Imidazole derivatives and pharmaceutical composition based on them

 

(57) Abstract:

Imidazole derivatives of the formula I, where R1- C1-20-alkyl, C4-12-cycloalkyl, C1-6-halogenated, oxoalkyl,8-13-areilly, C7-13-aralkyl, alkenyl, cycloalkyl, halogenated, oxoalkyl, aralkyl, areilly, hydroxy, nitro, NH2-NNSA(C1-6-alkyl or amino, substituted alkyl, aminoalkyl, carbamoyl or alkylsulfonyl; heteroallyl, including as heteroaryl 5-10-membered cycle, optionally benzoannelirovannykh, having as a heteroatom, 1 sulfur atom or nitrogen, optionally substituted by exography, alkyl, alkenyl, cycloalkyl, halogenation, oxoalkyl, aralkyl, arilalkilamin, hydroxy, alkoxy or amino (other deputies, see p. 1 formula). The compounds of formula I and pharmaceutical compositions on their basis have the ability to specific inhibition of proliferation of pathogenic HIV virus in the lymph nodes with low toxicity. 2 C. and 7 C.p. f-crystals, 6 PL.

The invention relates to new imidazole derivative and medicinal composition containing the derivative as an active ingredient.

AIDS (syndrome acquisition is no serious social problem all over the world, and so scientists around the world conduct research to develop drugs against HIV. Up to the present time the main purpose of these studies was derived nucleic acids, such as acidogenicity (AZT), dideoxyinosine (DDI), dideoxycytidine (DDC), dimethoxytetrahydrofuran (D4T) and 3'-thiacytidine (3TC), which are intended for clinical use, however, severe side effects and reduced efficiency due to the emergence of resistant strains, create new problems, and so the development of new drugs is currently very topical.

The pathological picture of AIDS are still not completely understood, and recently it was found that even in patients whose symptoms are absent, and whose condition is considered from the point of view of Virology as the latent period, there is a proliferation of the virus in the lymph nodes. Thus, the development of more effective drugs against HIV virus is currently a very important social value.

In this respect, it was a study of various derivatives of imidazole.

In U.S. patent (US, 3968228) description the x imidazole, used as intermediate compounds for the synthesis of these imidazolone drug compounds. However, in imidazole derivatives disclosed in this patent, the Deputy, is linked directly to the imidazole ring by-S-, -SO - or-SO2- limited to alkyl groups.

In U.S. patent 4592774 disclosed imidazole derivatives, which are used as herbicides, But all disclosed imidazole derivatives are optionally substituted phenylmethyl 2 polozenie imidazole ring.

In Japanese patent application Kokai-Hei-2-83373 revealed a series of imidazole derivatives possessing valuable properties due to which they can be used as pesticides, medicines, cosmetics or polymeric materials. These imidazole derivatives someseni 4 and/or 5-position by hydrogen, cyano group, carbamoyl group, thiocarbamoyl group or a group of the formula; COOR2(in this publication, they are represented by Deputy Y).

In Japanese patent application Kokai-Hei-5-252270 described imidazole derivatives having activity against HIV. However, in the disclosed derivatives of imidazole, the substituent in the 1-position of imidazole the Dublin core from the above state of modern science, we developed the present invention, the purpose of which is to obtain compounds with the ability to specific inhibition of proliferation of pathogenic HIV virus in the lymph nodes, and also has low toxicity.

The authors of this application it was found that the number of derivatives of imidazole, having defined below replacement group, satisfy the above objectives, based on which we developed the present invention. Thus, the present invention relates, generally, to any of such imidazole derivatives, and to pharmaceutical compositions containing these derivatives as the active ingredient.

Below is a detailed description of the present invention.

Imidazole derivatives of the present invention have the following formula (I):

< / BR>
where R1represents hydrogen, alkyl group with 1-20 carbon atoms, alkenylphenol group with 2-7 carbon atoms, cycloalkylcarbonyl group with 4-12 carbon atoms, halogenation group with 1-6 carbon atoms, oxoalkyl group with 1-6 carbon atoms, aroylamino group with 8 to 13 carbon atoms, substituted or unsubstituted aracelio group is th, carbamoyloximes or aryloxyalkyl group or branched hydroxyalkyl group;

R2represents an alkyl group with 1-6 carbon atoms, acyl group with 1-6 carbon atoms, hydroxylaminopurine group, hydroconseil group or a group of the formula: -(CH2)n-R4(where R4represents halogen, alkoxy group, hydroxy group, cyano group, acyloxy group, aryloxypropanolamine group, alkoxycarbonyl group, carboxy group, substituted or unsubstituted karbamoilnuyu group, substituted or unsubstituted, hydroxyalkyloxy group, substituted or unsubstituted benzyloxy group, a substituted or unsubstituted, carbamoylated or thiocarbamoyl group, substituted or unsubstituted amino group or azido-group;

and n is an integer of 1-3);

R3represents a substituted or unsubstituted alkyl group with 1-6 carbon atoms;

X and Y independently represent hydrogen, alkyl group with 1-3 carbon atoms, halogen or nitro group;

Z is S, SO, SO2or CH2.

In the above formula, the "alkyl group with 1-20 carbon atoms" represented by R1means spicy or times opentel, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, t-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, n-octadecyl, n-Needell, n-eicosyl etc.

Alkenylphenol group with 2-7 carbon atoms represented by R1are, without any restrictions, vinyl, allyl, propenyl, butenyl, pentenyl, hexenyl, heptenyl etc.

Cycloalkyl group with 4-12 carbon atoms represented by R1that is, without any restrictions, cyclopropylmethyl; 1 - or 2-cyclopropylethyl; 1-, 2 - or 3-cyclopropylmethyl; 1-, 2-, 3 - or 4-cyclopropylmethyl; 1-, 2-, 3-, 4- or 5-cyclopropylmethyl; 1-, 2-, 3-, 4-, 5- or 6-cyclopropylethyl; 1-, 2-, 3-, 4-, 5-, 6- or 7-cyclopropylethyl, 1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-cyclopropylethyl, 1-, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-cyclopropylmethyl; cyclobutylmethyl, 1 - or 2-cyclobutylmethyl, 1-, 2 - or 3-cyclobutylmethyl; 1-, 2-, 3 - or 4-cyclobutylmethyl; 1-, 2-, 3-, 4- or 5-cyclobutylmethyl; 1-, 2-, 3-, 4-, 5- or 6-cyclobutylmethyl; 1-, 2-, 3-, 4-, 5-, 6- or 7-cyclobutylmethyl; 1-, 2-, 3-, 4-, 5-, 6-, 7- or 8-cyclobutylmethyl, cyclopentylmethyl; 1 - or 2-cyclopentylmethyl; 1-, 2 - or 3-cyclopentylpropionyl; 1-, 2-, 3 - or 4-cyclopentylmethyl; 1-, 2-, 3-, 4- or 5-cyclopentylmethyl; 1-, 2-, 3-, 4-, 5- or 6-cyclopentyloxy; 1-, 2-, 3-, 4-, 5-, 6-, or 7-cyclopentylmethyl; C and 5-cyclohexylmethyl; 1-, 2-, 3-, 4-, 5- or 6-cyclohexyloxy; cycloheptylmethyl; 1-or 2-cycloheptylmethyl; 1-, 2 - or 3-cycloheptenyl; 1-, 2-, 3 - or 4-cycloheptylmethyl; 1-, 2-, 3-, 4- or 5-cycloheptylmethyl; cycloheptylmethyl; 1 - or 2-cyclooctylmethyl; 1-, 2 - or 3-cyclooctylmethyl; 1-, 2-, 3 - or 4 - cyclooctylmethyl; 1 - or 2-cyclooctylmethyl; 1-, 2 - or 3-cyclononylmethyl etc.

Halogenoalkanes group with 1-6 carbon atoms represented by R1are without any restrictions, chloromethyl, 1 - or 2-chloroethyl; 1-, 2 - or 3-chlorpropyl; 1-, 2-, 3 - or 4-chlorobutyl; 1-, 2-, 3-, 4- or 5-chloropentyl; 1-, 2-, 3-, 4-, 5- or 6-chlorhex; methyl bromide; 1 - or 2-bromacil; 1-, 2 - or 3-bromopropyl; 1-, 2-, 3 - or 4-bromobutyl; 1-, 2-, 3-, 4-. or 5-bromopentyl; 1-, 2-, 3-, 4-, 5- or 6-bromohexyl; vermeil; 1 - or 2-foretel; 1-, 2 - or 3-forproper; 1-, 2-, 3 - or 4-terbutyl; 1-, 2-, 3-, 4- or 5-terpencil; 1-, 2-, 3-, 4-, 5- or 6-forhekset; iodomethyl; 1 - or 2-Iodate; 1-, 2 - or 3-improper; 1-, 2-, 3 - or 4-iodobutyl; 1-, 2-, 3-, 4- or 5-iopentol; 1-, 2-, 3-, 4-, 5- or 6-iohexol; deformity; 1,2-dottorati; trifluoromethyl; 2,2,2-triptorelin etc.

Oxoalkyl group with 1-6 carbon atoms represented by R1and do not have any specific restrictions are acetylethyl, propicillin, 2-oxoethyl etc.

Kalkilya grtel; 1 - or 2-phenylethyl; 1-, 2 - or 3-phenylpropyl; 1-, 2-, 3 - or 4-phenylbutyl; 1-, 2-, 3-,4- or 5-fenilpentil; 1-, 2-, 3-, 4-, 5- or 6-phenylhexa; 1-, 2-, 3-, 4-, 5-, 6- or 7-phenylheptane; naphthylmethyl; 1 - or 2-naphtalate; etc.

Royalmile group with 8 to 13 carbon atoms represented by R1and do not have any specific restrictions are benzoylmethyl; 1 - or 2-benzoylethyl; 1-, 2 - or 3-benzoylpropionic; 1-, 2-, 3 - or 4-benzoylmethyl; 1-, 2-, 3-, 4- or 5-benzoylphenyl; 1-, 2-, 3-, 4-, 5- or 6-benzoyloxy; 1-, 2-, 3-, 4-, 5-, 6- or 7-benzoylmethyl; etc.

Heteroallyl group mentioned in the definition of R1and without any particular limitation, are 2-pyridylmethyl; 3-pyridylmethyl; 4-pyridylmethyl, 1 - or 2-(2-pyridyl)ethyl; 1 - or 2-(3-pyridyl)ethyl, 1 - or 2 - (4-pyridyl)ethyl; 1-, 2 -, or 3-(2-pyridyl)propyl; 2-thienylmethyl; 3-thienylmethyl, 4-thienylmethyl, 2-chenailler, 3-chenailler, 4-chenailler; etc.

Carbamoylated group mentioned in the definition of R1and do not have any specific restrictions are carbamoyloxymethyl; 1 - or 2-carbamoyloximes; 1-, 2 - or 3-carbamoyloximes; 1-, 2-, 3 - or 4-carbamoyloximes; etc.

Carbamoyloximes group mentioned in the definition of R1and not AI, etc.

Aryloxyalkyl group mentioned in the definition of R1and do not have any specific restrictions are acetoacetyl, propionylacetate etc.

Hydroxyalkyl group mentioned in the definition of R1and without any particular limitation, are 2-hydroxy-1-propyl, 2-hydroxy-2-propyl, 2-hydroxy-3-propyl, etc.

Deputy, which may be present on such groups represented by R1as substituted or unsubstituted aralkyl, substituted or unsubstituted heteroaromatic, or substituted or unsubstituted carbamoyloximes, carbamoyloximes or aryloxyalkyl, and which does not have any specific restrictions are alkyl (e.g. methyl, ethyl), alkenyl (for example, allyl), cycloalkyl (for example, cyclopropyl), halogenated (for example, permitil), oxoalkyl (for example, acetylethyl), aralkyl (e.g., benzyl), areilly (for example, benzoylmethyl), hydroxy group, substituted or unsubstituted amino group (for example, N-methylamino-, N,N-dimethylamino-N-acetylamino-, diaminomaleonitrile, freedomites, methanesulfonylaminoethyl).

In the above formula, the alkyl group with 1-6 carbon atoms, predstavleniya, mentioned in connection with the definition of R1. Acyl group with 1-6 carbon atoms represented by R2and R4and without any particular limitation, is formyl, acetyl, propionyl, butyryl, valeryl etc.

Alkoxy group mentioned in the definition of R4and without any particular limitation, may be, for example, methoxy, ethoxy-, propoxy - or butoxy group.

Aryloxypropanolamine group mentioned in the definition of R4and without any particular limitation, is, for example, vinyloxycarbonyloxy group.

Alkoxycarbonyl group mentioned in the definition of R4and without any particular limitation, is for example, ethoxycarbonyl group.

Hydroxyalkyloxy group mentioned in the definition of R4and without any particular limitation, is hydroxyethyloxy, hydroxyethyloxy group, etc.

Deputy, which may be present in the groups represented by R4such as substituted or unsubstituted carbarnoyl, substituted or unsubstituted, hydroxyalkyloxy group, substituted or unsubstituted benzyloxy group, a substituted or nezame who has any restrictions, is alkyl, alkenyl, cycloalkenyl, halogenated, oxoalkyl, acyl, carbarnoyl, and substituted or unsubstituted amino group (for example, N-methylamino, N,N-dimethylamino, N-acetylamino, diaminomaleonitrile, freedomites, methanesulfonylaminoethyl).

In the above formula, the alkyl group with 1-6 carbon atoms, referred to in the definition of R3is straight or branched alkyl group, which represents the same alkyl groups with 1-6 carbon atoms, which are indicated in the definition of R1. Thus, the preferred alkyl group is isopropyl. Deputy for such alkyl group has no particular restriction and represents hydroxy, alkoxy, acyloxy, alkenyl, cycloalkyl, halogen, oxoalkyl, aralkyl, areilly, cyano, carboxy, alkoxycarbonyl (for example, methoxycarbonyl, etoxycarbonyl), etc.

In the above formula is an alkyl group with 1-3 carbon atoms, referred to in the definition of X, has no specific limitation, and can be, for example, stands, ethyl or propylene. The halogen represented by X, has no specific limitation, and is chlorine, bromine, fluorine and iodine. When this predpochtitelnei Y, has no specific limitation, and can be, for example, stands, ethyl or propylene. The halogen represented for Y, has no particular restriction and can be chlorine, bromine, fluorine and iodine. While preferred is chlorine.

Below is a list of preferred compounds of the present invention.

(A-1) 2-Carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(A-2) 2-[5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]ethanol;

(A-3) 2-Carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-4-yl)methyl-1H-imidazole;

(A-4) [5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl]methanol;

(A-5) [1-(2-Hydroxypropyl)-5-(3,5-dichlorophenylthio-4-isopropyl-1H-imidazol-2-yl]methanol;

(A-6) [5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl] acetonitrile;

(A-7) [5-(3,5-Dichlorophenylthio)-1-(4-aminobenzyl)-4-isopropyl-1H-imidazol-2-yl]methanol;

(A-8) [5-(3,5-Dichlorophenylthio)-1-(3-aminobenzyl)-4-isopropyl-1H-imidazol-2-yl]methanol;

(A-9) 2-[5-(3,5-Dichlorophenylthio)-4-isopropyl-1-ethyl-1H-imidazol-2-yl] ethanol;

(A-10) 2-[2-(Carbamoylated)ethyl] -5-(3,5-dichlorophenylthio-1-ethyl-4-isopropyl-1H-imidazole;

(A-11) [5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(6-oxo-1,6-dihydropyridines-3-h-3-yl)methyl-4-isopropyl-1H-imidazole.

In addition to the above compounds of the present invention includes, for example, the following connections:

(1) 2-Carbamoyloxymethyl-5-isopropyl-1-methyl-4-phenylthio-1H-imidazole;

(2) the Reaction of 5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole-2-carbaldehyde;

(3) 4-(3,5-Differenlty)-5-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde;

(4) Methyl-3-(5-(3,5-differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)propionate;

(5) 2-(5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)ethanol;

(6) Hydrazone 5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole-2-carbaldehyde;

(7) 2-(2-Carbamoylethyl)-4-isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole;

(8) 2-(2-Carbamoylethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1-methyl-1H-imidazole;

(9) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1-(2-phenylethyl)-H-imidazole;

(10) 2-(2-Carbamoyloximes)methyl-1-ethyl-4-isopropyl-5-phenylthio-1H-imidazole;

(11) 2-(2-Carbamoylethyl)-5-(3,5-dimethylphenyl)-1-ethyl-4-isopropyl-1H-imidazole;

(12) 2-(2-Carbamoyloximes)methyl-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(13) 2-(2-Carbamoyloximes)methyl-5-(3-nitrophenylthio)-1-ethyl-4-isopropyl-1H-imide-1-methyl-1H-imidazole;

(16) 2-Azidomethyl-4-(3,5-differenlty)-1-ethyl-5-isopropyl-1H-imidazole;

(17) 4-Isopropyl-2-N-methyl(thiocarbamoyl)oxymethyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole.

(18) 5-(3,5-Dimethylphenyl)-4-isopropyl-1-n-propyl-1H-imidazol-2-ylmethanol;

(19) 2-(2-Carbamoylethyl)-4-isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazole;

(20) 2-(2-Acetoxyethyl)-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(21) 3-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)propanol;

(22) 4-Isopropyl-2-N-methylcarbamoylmethyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole;

(23) 4-Isopropyl-1-methyl-5-(3-forfinally)-1H-imidazol-2-ylacetonitrile;

(24) 1-(5-(3,5-Dichlorophenylthio)-2-(3-carbamoyloximes)-4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(25) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-1-vermeil-4-isopropyl-1H-imidazole;

(26) 2-Carbamoyloxymethyl-4-isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazole;

(27) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylacetonitrile;

(28) Methyl-3-(5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)propionate;

(29) Hydrazone 5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole-2-carbaldehyde;

(32) 1-Benzyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-2-ylmethanol;

(33) 2-(2-Carbamoyloximes)methyl-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(34) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylmethanol;

(35) 2-(2-Carbamoylethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(36) 2-Aminomethyl-4-isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazole;

37) 1-Benzyl-2-(3-carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(38) 5-(3,5-Differenlty)-2-dimethylaminomethyl-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(39) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1-n-propyl-1H-imidazole;

(40) 2-2-(Acetoxyethyl)-5-(3,5-differenlty)-4-isopropyl-1-methyl-1H-imidazole;

(41) 2-(2-Carbamoylethyl)-5-(3,5-dimethylphenyl)-1-hexyl-4-isopropyl-1H-imidazole;

(42) 5-(3,5-Differenlty)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazol-2-ylmethanol;

(43) 2-Carbamoyloxymethyl-5-(3,5-dimethylphenyl)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazole;

(44) 2-(2-amino-ethyl)-1-ethyl-4-isopropyl-5-phenylthio-1H-imidazole;

(45) 1-Allyl-2-(3-carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(46) 2-(1-Allyl-5-(3,5-differenl is metoxi)ethanol;

(48) -(2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(49) 3-(1-(4-Aminobenzyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-2-yl)propanol;

(50) 2-Carbamoyloxymethyl-1-cyclopropylmethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(51) 2-Azidomethyl-4-(3-chlorophenylthio)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(52) N-(5-(3,5-Dichloraniline)-1-ethyl-4-isopropyl-1H-imidazole-4-ylmethyl)acetamide;

(53) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1-methyl-1H-imidazole;

(54) -(2-(2-Hydroxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(55) 1-Allyl-2-(3-carbamoylmethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazole;

(56) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole-2-carbaldehyde;

(57) 5-(3,5-Dichlorophenylthio)-4-isopropyl-2-N-methylcarbamoylmethyl-1-(- perigee-4-ylmethyl)-1H-imidazole;

(58) 2-Azidomethyl-4-isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole;

(59) 2-(4-Isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(60) 2-Acetamidomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(61) 2-(5-(3,5-Dichlorophenylthio)-1-hexyl-4-isopropyl-1H-imidazol-2-yl)ethanol;

(62) 1-Ethyl-5-isoprenylation)-1H-imidazole;

(64) -(5-(3,5-Differenlty)-2-(3-hydroxypropyl)-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(65) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(3-(pyridin-4-yl)propyl-1H-imidazol-2-ylmethanol;

(66) 5-(3-Chlorophenylthio)-2-dimethylaminomethyl-1-ethyl-4-isopropyl-1H-imidazole;

(67) 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(quinoline-3-ylmethyl)-1H-imidazol-2-yl)ethanol;

(68) 2-Carbamoyloxymethyl-4-isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazole;

(69) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylacetonitrile;

(70) 2-Acetamidomethyl-5-(3,5-differenlty)-1-ethyl-4-isopropyl-1H-imidazole;

(71) the Reaction of 5-(3,5-differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole-2-carbaldehyde;

(72) 5-(3,5-Dichlorophenylthio)-2-dimethylaminomethyl-4-isopropyl-1-methyl-1H-imidazole;

(73) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-1-ethyl-4-isopropyl-1H-imidazole;

(74) 2-(1-Ethyl-4-isopropyl-5-(3-forfinally)-1H - imidazol-2-yl)ethanol;

(75) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylacetic;

(76) 4-Isopropyl-1-methyl-5-phenylthio-1H-imidazol-2-ylacetic;

(77) 1-Benzyl-2-carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(78) 4-Isopropyl-2-N-methylcarbamoylmethyl-5-phenylthio-1-(pyridine-2-ylmethyl) is aminomethyl-4-isopropyl-1-methyl-5-(3-forfinally)-1H-imidazole;

(81) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole-2-carbaldehyde hydrazone;

(82) 4-Isopropyl-1-methyl-5-phenylthio-1H-imidazol-2-ilmatieteen;

(83) 2-Aminomethyl-4-(3,5-differenlty)-5-isopropyl-1-methyl-1H-imidazole;

(84) 5-(3,5-Differenlty)-1-ethyl-4-isopropyl-1H-imidazole-2-carbaldehyde;

(85) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylacetic;

(86) 2-(4-Isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(87) 4-Isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-2-freedomites-1H-imidazole;

(88) 2-(5-(3,5-Differenlty)-1-hexyl-4-isopropyl-1H-imidazol-2-yl)ethanol;

(89) 5-(3,5-Differenlty)-4-isopropyl-1-methyl-1H-imidazol-2-ylacetonitrile;

(90) 2-Carbamoyloxymethyl-4-(3,5-differenlty)-1-ethyl-5-isopropyl-1H-imidazole;

(91) 4-Isopropyl-2-N-methylcarbamoylmethyl-1-methyl-5-phenylthio - 1H-imidazole;

(92) 5-(3-Nitrophenylthio)-4-isopropyl-2-methanesulfonamido-1-methyl-1H-imidazole;

(93) 5-(3,5-Differenlty)-4-isopropyl-1-methyl-2-N-methylthiocarbamate-1H-imidazole;

(94) -(2-(2-Hydroxyethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(95) 4-Isopropyl-2-N-methylcarbamoylmethyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole;

(98) 2-(4-(3-Nitrophenylthio)-1-ethyl-5-isopropyl-1H-imidazol-2-ylethoxy)ethanol;

(99) 2-Acetamidomethyl-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(100) Hydrazone of 1-ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazole-2-carbaldehyde;

(101) 2-Dimethylaminomethyl-4-isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazole;

(102) 5-(3,5-Dichlorophenylthio)-4-isopropyl-2-N-methylcarbamoylmethyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(103) 1,4-Dibenzyl-5-isopropyl-1H-imidazol-2-ylmethanol;

(104) 5-(3,5-Differenlty)-4-isopropyl-1-methyl-1H - imidazol-2-ilmatieteen;

(105) 2-Carbamoyloxymethyl-4-(3,5-differenlty)-5-isopropyl-1-methyl-1H-imidazole;

(106) 5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-2-N-methylaminomethyl-1H-imidazole;

(107) 2-2-(Acetoxyethyl)-4-isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole;

(108) Hydrazone 5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde;

(109) 1-(2-Aminobenzyl)-5-(3,5-dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1H-imidazole;

(110) 2-Carbamoyloxymethyl-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(111) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-1-hexyl-4-isopropyl-1H-imidazole;

(112) 1-(2-(2-Hydroxyethyl)-5-(3,5-dimethylphenyl)-4-isodata;

(114) 2-(5-(3,5-Differenlty)-4-isopropyl-1-methyl-1H-imidazol-2-ylethoxy)ethanol;

(115) 2-(2-Carbamoylethyl)-5-(3-nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(116) 1-n-Butyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazol-2-ylmethanol;

(117) 1-(2-Carbamoylethyl)-2-(3-carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(118) 2-(4-Isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazol-2-yl)ethanol;

(119) Hydrazone of 4-isopropyl-1-methyl-5-(3-formailty)- 1H-imidazole-2-carbaldehyde;

(120) 1-n-Butyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-ylmethanol;

(121) 2-(5-(3,5-Dichlorophenylthio)-1,4-aminobutiramida-1H-imidazol-2-yl)ethanol;

(122) 5-(3,5-Differenlty)-4-isopropyl-2-methanesulfonamido-1-methyl-1H-imidazole;

(123) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1-(3-phenylpropyl)-1H-imidazole;

(124) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(125) 5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-4-isopropyl-1-n-propyl-1H-imidazole;

(126) 4-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-1-ethyl-5-isopropyl-1H-imidazole;

(127) 2-(1-Ethyl-4-isopropyl-5-phenylthio-1H-imidazol-2-yl)-ethanol;

(128) 5-(3-Chlorophenylthio)-4-isopropyl-2-N-methylthiocarbamate-1-(/BR> (130) 2-Aminomethyl-4-(3,5-dichlorophenylthio)-1-ethyl-5-isopropyl-1H-imidazole;

(131) 2-(2-Carbamoyloximes)methyl-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(132) 2-Azidomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(133) 2-(2-amino-ethyl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(134) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1-methyl-1H-imidazole;

(135) 5-(3-Nitrophenylthio)-4-isopropyl-1-methyl-2-N-methyl-carbamoyloxymethyl-1H-imidazole;

(136) 5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ilmatieteen;

(137) 5-(3,5-Differenlty)-4-isopropyl-1-methyl-1H-imidazol-2-ylacetic;

(138) N-(5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-4-ylmethyl)acetamide;

(139) Isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazole-2-carbaldehyde hydrazone;

(140) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ylacetonitrile;

(141) 2-(5-(3,5-Dichlorophenylthio-1-ethyl-4-isopropyl-1H-imidazol-2-retoxification;

(142) 2-(2-Carbamoylethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1-n-propyl-1H-imidazole;

(143) 1-(3-Aminobenzyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-2-ylmethanol;

(144) 5-(3-Nitrophenylthio)-4-isopro hydropyridine-3-yl)methyl-1H-imidazol-2-yl)propanol;

(146) 3-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(2-phenylethyl)-1H-imidazol-2-yl)propanol;

(147) N-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-4-ylmethyl)acetamide;

(148) 5-(3,5-Dichlorophenylthio)-1-(2-carbamoylethyl)-2-carbamoyloxymethyl-4-isopropyl-1H-imidazole;

(149) 5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-4-isopropyl-1-(2-(pyridin-4-yl)ethyl)-1H-imidazole;

(150) 2-(2-Azidoethyl)-5-(3-chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(151) N-(4-Isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazol-4-ylmethyl)acetamide;

(152) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-(2,2-triptorelin)-1H-imidazole;

(153) N-(1-Ethyl-4-isopropyl-5-phenylthio-1H-imidazol-4-ylmethyl)acetamide;

(154) 5-(3,5-Dichlorophenylthio)-2-diaminomethylene-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(155) 5-(3,5-Dichlorophenylthio)-2-dimethylaminomethyl-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(156) 5-(3,5-Differenlty)-4-isopropyl-1-(2-phenylethyl)-1H-imidazol-2-ylmethanol;

(157)-(2-(2-Carbamoylethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(158) 2-Azidomethyl-4-(3-nitrophenylthio)-1-ethyl-5-isopropyl-1H-imidazole;

(159) 5-(3,5-Differenlty)-4-isopropyl-1-methyl-1H-imidazol-2-ylmethanol;

(160) Hydras is 1-ethyl-5-isopropyl-4-phenylthio-1H-imidazole;

(162) 2-(1-(2-Aminobenzyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(163) 1-Cyclopropylmethyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazol-2-ylmethanol;

(164) 2-(5-(3,5-Dimethylphenyl)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanol;

(165) -(5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(166) 2-Acetamidomethyl-5-(3,5-differenlty)-4-isopropyl-1-methyl-1H-imidazole;

(167) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(168) Methyl 3-(5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-yl)propionate;

(169) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazol-2-ylmethanol;

(170) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1-(2-methylpyridin-3-ylmethyl)-1H-imidazole;

(171) N-(4-Isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazol-4-ylmethyl)acetamide;

(172) 1-(3-Aminobenzyl)-2-(2-carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(173) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylacetic;

(174) 1-(2-Aminobenzyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-ylmethanol;

(175) 2-(2-Carbamoylethyl)-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-they shall velociprey)-1-cyclopropylmethyl-5-(3,5 - differenlty)-4-isopropyl-1H-imidazole;

(178) 2-(2-Carbamoylethyl)-1-ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazole;

(179)-5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole-2-carbaldehyde hydrazone;

(180) 2-Acetamidomethyl-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(181) 2-Carbamoyloxymethyl-4-isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole;

(182) 2-(5-(3,5-Dimethylphenyl)-4-isopropyl-1-n-propyl-1H-imidazol-2-yl)ethanol;

(183) N-(4-Isopropyl-1-methyl-5-(3-forfinally)-1H-imidazol - 4-ylmethyl)acetamide;

(184) 2-(2-amino-ethyl)-4-isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazole;

(185) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(186) N-(5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-4-ylmethyl)acetamide;

(187) 5-(3,5-Dimethylphenyl)-1-vermeil-4-isopropyl-1H-imidazol-2-ylmethanol;

(188) 2-(2-Acetoxyethyl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(189) 4-(3,5-Dimethylphenyl)-5-isopropyl-1-methyl-1H-imidazol-2-ylmethanol;

(190) 5-(3-Nitrophenylthio)-4-isopropyl-1-methyl-2-N-methylaminomethyl-1H-imidazole;

(191) 5-(3-Chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ylacetic;

(192) 2-(2-Carbamoylethyl)-5-(3-chlorophenylthio-1H-imidazole;

(194) 2-Azidomethyl-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(195) 2-(5-(3,5-Dichlorophenylthio)-1-(2-carbamoylethyl)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(196) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-2-freedomites-1H-imidazole;

(197) 1-(2-(2-Hydroxyethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)-2-propanone;

(198) 5-(3,5-Dichlorophenylthio)-1-cyclopropylmethyl-4-isopropyl-1H-imidazol-2-ylmethanol;

(199) 1-Allyl-2-carbamoyloxymethyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazole;

(200) 5-(3,5-Dichlorophenylthio)-2-(3-carbamoyloximes)-4-isopropyl-1-methyl-1H-imidazole;

(201) 2-Carbamoyloxymethyl-4-isopropyl-1-methyl-5-phenylthio-1H-imidazole;

(202) 3-(1-Cyclopropylmethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)propanol;

(203) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-2-freedomites-1H-imidazole;

(204) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ilmatieteen;

(205) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-methyl-1H-imidazole;

(206) 5-(3,5-Dichlorophenylthio)-2-(3-carbamoyloximes)-4-isopropyl-1-(2-phenylethyl)-1H-imidazole;

(207) 2-(2-Azidoethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(208) 4-Isopropyl-2-N-Mel)-1H-imidazol-2-yl)ethanol;

(210) 3-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(6-oxo-1,6-dihydropyridines-3-yl)methyl-1H-imidazol-2-yl)propanol;

(211) 2-Diaminomethylene-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(212) 2-(4-Isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylethoxy)ethyl acetate;

(213) 2-Diaminomethylene-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(214) 5-(3-Chlorophenylthio)-1-ethyl-4-isopropyl-2-freedomites-1H-imidazole;

(215) 3-(1,4-Aminobutiramida-5-(3,5-differenlty)-1H-imidazol-2-yl)propanol;

(216) 2-(2-amino-ethyl)-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-;

(217) 1-(3-Aminobenzyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-ylmethanol;

(218) 2-(5-(3,5-Differenlty)-4-isopropyl-1-(3-(pyridin-4-yl)propyl)-1H-imidazol-2-yl)ethanol;

(219) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole-2-carbaldehyde

(220) 3-(1-(2-Aminobenzyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)propanol;

(221) 2-(2-Carbamoyloximes)methyl-5-(3,5-differenlty)-4-isopropyl-1-methyl-1H-imidazole;

(222) 1-Allyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-ylmethanol;

(223) 2-(1-Benzyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(224) 2-(3-Carbamoylmethyl)-2-(3-carbamoyloximes)-1-hexyl-4-isopropyl-1H-imidazole;

(226) 2-(2-Acetoxyethyl)-4-isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazole;

(227) 5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole-2-carbaldehyde;

(228) 5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ylacetic;

(229) 2-Acetamidomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(230) 2-(2-Acetoxyethyl)-4-isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole;

(231) 2-Carbamoyloxymethyl-4-(3,5-dimethylphenyl)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(232) 2-(2-Azidoethyl)-4-isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazole;

(233) N-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-4-ylmethyl)acetamide;

(234) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-2-freedomites-1H-imidazole;

(235) 2-Aminomethyl-4-isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole;

(236) 3-(5-(3,5-Dimethylphenyl)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-yl)propanol;

(237) 2-(5-(3,5-Differenlty)-4-isopropyl-1-(2-(pyridin-4-yl)ethyl)-1H-imidazol-2-yl)ethanol;

(238) 4-(3,5-Dichlorophenylthio)-5-isopropyl-1-methyl-1H-imidazol-2-ilmatieteen;

(239) 5-(3,5-Dichlorophenylthio)-1,2-bis-(2-carbamoylethyl)-4-isopropyl-1H-imidazole;

(240) 2-(5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imitatores-2-N-methylcarbamoylmethyl-1-methyl-5-phenylthio-1H-imidazole;

(243) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(244) 5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-1-vermeil-4-isopropyl-1H-imidazole;

(245) 4-(3,5-Dimethylphenyl)-1-vermeil-5-isopropyl-1H-imidazol-2-ylmethanol;

(246) 2-Aminomethyl-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(247) 1-Ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazole-2-carbaldehyde;

(248) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylacetonitrile;

(249) 5-(3,5-Dichlorophenylthio)-4-isopropyl-2-N-methylthiocarbamate-1-(pyridine-4-ylmethyl)-1H-imidazole;

(250) 2-(5-(3,5-Differenlty)-1,4-aminobutiramida-1H-imidazol-2-yl)ethanol;

(251) 5-(3,5-Dichlorophenylthio)-2-(3-carbamoyloximes)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(252) Methyl 3-(4-isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazol-2-yl)propionate;

(253) 2-(5-(3,5-Dimethylphenyl)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)ethanol;

(254) 5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-2-N-methylthiocarbamate-1H-imidazole;

(255) N-(4-Isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazol-4-ylmethyl)acetamide;

(256) 5-(3-Nitrophenylthio)-4-isopropyl-2-N-methylcarbamoylmethyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(257) the Il-1-methyl-1H-imidazole;

(259) 4-Isopropyl-1-methyl-5-(3-forfinally)-1H-imidazol-2-ylacetic;

(260) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole-2-carbaldehyde hydrazone;

(261) 2-(2-Carbamoylethyl)-4-isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazole;

(262) 2-(3-Carbamoylmethyl)-5-(3-nitrophenylthio)-4-isopropyl-1-(- perigee-4-ylmethyl)-1H-imidazole;

(263) 4-Isopropyl-2-N-methylaminomethyl-1-methyl-5-(3-forfinally)-1H-imidazole;

(264) 2-(4-(3-Chlorophenylthio)-5-isopropyl-1-methyl-1H-imidazol-2-ylethoxy)ethanol;

(265) Methyl 3-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)propionate;

(266) 1-(5-(3,5-Dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(267) 2-(1-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(268) 4-(3-Chlorophenylthio)-1-ethyl-5-isopropyl-1H-imidazol-2-ilmatieteen;

(269) 5-(3,5-Dichlorophenylthio)-2-dimethylaminomethyl-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(270) 2-Aminomethyl-4-isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazole;

(271) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-2-freedomites-1H-imidazole;

(272) 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ylethoxy)ethyl acetate;

(273) Hydrazone 5-(3-nitrophenylthio)-4-and the ol-4-ylmethyl)acetamide;

(275) 5-(3-Chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole-2-carbaldehyde;

(276) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylacetonitrile;

(277) 1-(2-Aminobenzyl)-2-(3-carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(278) 2-Carbamoyloxymethyl-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(279) 5-(3-Nitrophenylthio)-1-ethyl-4-isopropyl-2-N-methylthiocarbamate-1H-imidazole;

(280) 5-(3-Chlorophenylthio)-4-isopropyl-2-N-methylaminomethyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(281) 1-(4-Aminobenzyl)-5-(3,5-dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1H-imidazole;

(282) 4-Isopropyl-1-methyl-5-phenylthio-1H-imidazol-2-ylacetonitrile;

(283) 2-(4-(3,5-Differenlty)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(284) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-2-freedomites-1H-imidazole;

(285) 1-n-Butyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-ylmethanol;

(286) 2-(2-Carbamoyloximes)methyl-4-isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazole;

(287) 2-(2-Carbamoylethyl)-4-isopropyl-1-methyl-5-(3-forfinally)-1H-imidazol;

(288) the Reaction of 5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole-2-carbaldehyde

(289) 5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(291) 5-(3,5-Dichlorophenylthio)-4-isopropyl-2-N-methylaminomethyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(292) 2-(2-Azidoethyl)-5-(3-nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(293) 5-(3,5-Dimethylphenyl)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazol-2-ylmethanol;

(294) 1-n-Butyl-2-carbamoyloxymethyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazole;

(295) 2-(5-(3,5-Differenlty)-4-isopropyl-1-methyl-1H-imidazol-2-ylethoxy)ethyl acetate;

(296) 2-Diaminomethylene-4-isopropyl-1-methyl-5-phenylthio-1H-imidazole;

(297) 4-(3,5-Differenlty)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ilmatieteen;

(298) 2-Carbamoyloxymethyl-4-(3,5-differenlty)-1-vermeil-5-isopropyl-1H-imidazole;

(299) 2-Carbamoyloxymethyl-4-(3-nitrophenylthio)-1-ethyl-5-isopropyl-1H-imidazole;

(300) N-(4-Isopropyl-1-methyl-5-phenylthio-1H-imidazol-4-ylmethyl)acetamide;

(301) N-(4-Isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazol-4-ylmethyl)acetamide;

(302) 2-(3-Carbamoyloximes)-1-ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazole;

(303) 2-Diaminomethylene-5-(3,5-differenlty)-4-isopropyl-1-methyl-1H-imidazole;

(304) 5-(3-Chlorophenylthio)-4-isopropyl-2-N-methyl(thiocarbamoyl)-oxymethyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(305) 3-(5-(3-Nitrophenylthio)-4-carbaldehyde the oxime;

(307) 2-Acetamidomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(308) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazole-2-carbaldehyde;

(309) 5-(3-Chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde hydrazone;

(310) 2-Carbamoyloxymethyl-1-cyclopropylmethyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazole;

(311) 4-(3-Chlorophenylthio)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ilmatieteen;

(312) 3-(5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)propanol;

(313) 2-(2-amino-ethyl)-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(314) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylacetic;

(315) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylacetic;

(316) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-2-freedomites-1H-imidazole;

(317) 2-(4-Isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylethoxy)ethyl acetate;

(318) 1-Ethyl-4-isopropyl-5-(3-forfinally)-2-freedomites-1H-imidazole;

(319) 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(3-phenylpropyl)-1H-imidazol-2-yl)ethanol;

(320) 5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-4-isopropyl-1-(2-phenylethyl)-1H-imidazole;

(321) 5-(3,5-Differenl the-imidazole;

(323) 5-(3,5-Differenlty)-1-ethyl-4-isopropyl-1H-imidazol-2-ylacetonitrile;

(324) 2-Carbamoyloxymethyl-5-(3,5-dimethylphenyl)-1-forfinal-4-isopropyl-1H-imidazole;

(325) 4-Isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylacetonitrile;

(326) 1-Benzyl-4-(3,5-dimethylphenyl)-5-isopropyl-1H-imidazol-2-ylmethanol;

(327) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazole-2-carbaldehyde;

(328) 3-(4-Isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazol-2-yl)propanol;

(329) 1-(3-Aminobenzyl)-2-(3-carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(330) 1-Ethyl-5-isopropyl-4-(3-forfinally)-1H-imidazole-2-carbaldehyde;

(331) 5-(3,5-Dichlorophenylthio)-2-(3-carbamoyloximes)-4-isopropyl-1-(2-methylpyridin-3-ylmethyl)-1H-imidazole;

(332) 1-Ethyl-4-isopropyl-2-methanesulfonylaminoethyl-5-(3-forfinally)-1H-imidazole;

(333) 2-Azidomethyl-4-isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazole;

(334) 5-(3-Chlorophenylthio)-2-diaminomethylene-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(335) 5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-2-freedomites-1H-imidazole;

(336) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(337) 2-Carbamoyloximes-2-carbaldehyde hydrazone;

(339) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-2-freedomites-1H-imidazole;

(340) 5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylacetonitrile;

(341) 5-(3-Chlorophenylthio)-2-dimethylaminomethyl-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(342) 2-(5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylethoxy)ethyl acetate;

(343) 2-Acetamidomethyl-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(344) 3-(1-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)propanol;

(345) 5-Isopropyl-1-methyl-4-(3-forfinally)-1H-imidazol-2-ylmethanol;

(346) 2-Acetamidomethyl-4-isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazole;

(347) 2-(2-Carbamoylethyl)-1-cyclopropylmethyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazole;

(348) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-(2-phenylethyl)-1H-imidazole;

(349) 2-(2-Azidoethyl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(350) 5-(3-Nitrophenylthio)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde;

(351) 4-(3-Chlorophenylthio)-1-ethyl-5-isopropyl-1H-imidazole-2-carbaldehyde;

(352) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylacetonitrile;

(353) 4-Isopropyl-2-methylthio)-1-ethyl-5-isopropyl-1H-imidazole;

(355) 2-Aminomethyl-5-(3-nitrophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(356) 5-(3-Nitrophenylthio)-4-isopropyl-2-methanesulfonamido-1-(pyridine-2-ylmethyl)-1H-imidazole;

(357) 5-(3,5-Differenlty)-1-hexyl-4-isopropyl-1H-imidazol-2-ylmethanol;

(358) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-1-ethyl-4-isopropyl-1H-imidazole;

(359) 2-Aminomethyl-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(360) 3-(5-(3,5-Dimethylphenyl)-1-hexyl-4-isopropyl-1H-imidazol-2-yl)propanol;

(361) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole-2-carbaldehyde the oxime;

(362) 2-(5-(3,5-Differenlty)-1-hexyl-4-isopropyl-1H-imidazol-2-yl)ethanol;

(363) 2-(5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-yl)ethanol;

(364) 1-(2-(2-Carbamoylethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazol-1-yl)-2-propanol;

(365) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(quinoline-3-ylmethyl)-1H-imidazol-2-ylmethanol;

(366) Methyl-3-(1-ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazol-2-yl)propionate;

(367) 2-Aminomethyl-4-isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazole;

(368) 1-(5-(3,5-Differenlty)-2-(3-hydroxypropyl)-4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(369) 2-(2-Carbamoylethyl)-5-(3,5-dimethylphenyl)-1-formati) 4-Isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylacetic;

(372) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-1-ethyl-4-isopropyl-1H-imidazole;

(373) 5-(3,5-Differenlty)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde hydrazone;

(374) 2-(4-Isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazol-2-yl)ethanol;

(375) 2-(2-Acetoxyethyl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(376) 5-(3,5-Dimethylphenyl)-1-ethyl-4-isopropyl-1H-imidazol-2-ylmethanol;

(377) 5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-4-isopropyl-1-(2-methylpyridin-3-ylmethyl)-1H-imidazole;

(378) 2-Azidomethyl-4-(3-nitrophenylthio)-5-isopropyl-1-methyl-1H-imidazole;

(379) 1-Allyl-5-(3,5-dichlorophenylthio)-2-(3-carbamoyloximes)-4-isopropyl-1H-imidazole;

(380) 1-(5-(3,5-Dimethylphenyl)-2-hydroxymethyl)-4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(381) 2-(3-Carbamoylmethyl)-5-(3-chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(382) 2-Carbamoyloxymethyl-4-(3-nitrophenylthio)-5-isopropyl-1-methyl-1H-imidazole;

(383) 1-(4-Aminobenzyl)-2-carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(384) 5-(3,5-Dichlorophenylthio)-2-diaminomethylene-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(385) 2-Azidomethyl-5-(3-nitrophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(386) 2-(5-(3,5-Dichlorophenylthio)-4-isoprop-imidazole;

(388) 5-(3,5-Differenlty)-4-isopropyl-2-N-methylaminomethyl-1-(pyridine-2-ylmethyl)-1H-imidazole; 1 (389) 2-Acetamidomethyl-5-(3-chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(390) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1-n-propyl-1H-imidazole;

(391) 2-Aminomethyl-4-(3-chlorophenylthio)-5-isopropyl-1-methyl-1H-imidazole;

(392) 3-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(3-(pyridin-4-yl)propyl)-1H-imidazol-2-yl)propanol;

(393) 2-Diaminomethylene-4-isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole;

(394) 2-(3-Carbamoyloximes)-1,5-dibenzyl-4-isopropyl-1H-imidazole;

(395) 5-(3,5-Dichlorophenylthio)-1-n-butyl-4-isopropyl-1H-imidazol-2-ylmethanol;

(396) 2-(5-(3-Nitrophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ylethoxy)ethanol;

(397) 1-(5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(398) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-1-hexyl-4-isopropyl-1H-imidazole;

(399) 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanol;

(400) 5-(3-Nitrophenylthio)-4-isopropyl-2-N-methyl(thiocarbamoyl)-oxymethyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(401) 1-Benzyl-2-carbamoyloxymethyl-4-(3,5-differenlty)-5-isopropyl-1H-imidazole;

(402) 2-(1,5-Dibenzyl-4-isopropyl-1H-imidazol-2-yl)ethanol;


(405) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(406) 2-Carbamoyloxymethyl-5-(3,5-dimethylphenyl)-1-hexyl-4-isopropyl-1H-imidazol;

(407) 5-(3-Nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ylmethanol;

(408) 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ylethoxy)ethanol;

(409) 5-(3,5-Dichlorophenylthio)-2-(3-carbamoyloximes)-4-isopropyl-1-(3-phenylpropyl)-1H-imidazole;

(410) 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(3-(pyridin-4-yl)propyl)-1H-imidazol-2-yl)ethanol;

(411) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-1,4-aminobutiramida-1H-imidazole;

(412) 2-Azidomethyl-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(413) 1-(4-Aminobenzyl)-2-(2-carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(414) 5-(3-Nitrophenylthio)-2-dimethylaminomethyl-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(415) 2-(2-Carbamoylethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazole;

(416) 2-Carbamoyloxymethyl-4-(3,5-differenlty)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(417) 4-Isopropyl-2-N-methylaminomethyl-1-methyl-5-phenylthio-1H-imidazole;

(418) 4-(3,5-Dichlorophenylthio)-1-vermeil-5-isopropyl-1H-imidazol-2-ylmethanol;

(419) 5-Isopropyl-1-l-1H-imidazole;

(421) 4-Isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylmethanol;

(422) Methyl 3-(5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-yl)propionate;

(423) 5-(3,5-Dichlorophenylthio)-2-(3-carbamoyloximes)-4-isopropyl-1-(2-(pyridin-4-yl)ethyl)-1H-imidazole;

(424) 2-Aminomethyl-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(425) 2-Aminomethyl-4-isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole;

(426) 3-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazol-2-yl)propanol;

(427) 4-(3,5-Differenlty)-1-vermeil-5-isopropyl-1H-imidazol-2-ylmethanol;

(428) 2-Diaminomethylene-4-isopropyl-1-methyl-5-(3-forfinally)-1H-imidazole;

(429) 2-(5-(3,5-Differenlty)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)ethanol;

(430) -(2-Carbamoyloxymethyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(431) 1-(2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(432) 3-(5-(3,5-Differenlty)-4-isopropyl-1-n-propyl-1H-imidazol-2-yl)propanol;

(433) -(2-(2-Hydroxyethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(434) 2-Aminomethyl-4-isopropyl-1-methyl-5-(3-forfinally)-1H-imidazole;

(435) 2-(2-Carbamoyloximes)methyl-5-(3-chloral-1H-imidazole;

(437) 2-Diaminomethylene-4-isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazole;

(438) 2-(2-Carbamoyloximes)methyl-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(439) 3-(5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)propanol;

(440) 2-(2-Carbamoylethyl)-1-cyclopropylmethyl-5-(3,5-differenlty)-4-isopropyl-1H-Imidazole;

(441) 5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylacetonitrile;

(442) 2-(4-Isopropyl-1-methyl-5-phenylthio-1H-imidazol-2-yl)-ethanol;

(443) 2-(5-Isopropyl-1-methyl-4-phenylthio-1H-imidazol-2-ylethoxy)ethanol;

(444) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylacetonitrile;

(445) 2-Aminomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(446) 2-(5-(3,5-Dichlorophenylthio)-1-vermeil-4-isopropyl-1H-imidazol-2-yl)ethanol;

(447) 2-carbamoyloxymethyl-5-(3,5-dimethylphenyl)-1-ethyl-4-isopropyl-1H-imidazole;

(448) N-(5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-4-ylmethyl)acetamide;

(449) Methyl 3-(5-(3,5-differenlty)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)propionate;

(450) 5-(3,5-Differenlty)-4-isopropyl-1-(3-phenylpropyl)-1H-imidazol-2-ylmethanol;

(451) 2-(2-amino-ethyl-5-(3,5-dichlorophen is an imidazole;

(453) 1-(4-Aminobenzyl)-5-(3,5-dichlorophenylthio)-2-carbamoyloxymethyl-4-isopropyl-1H-imidazole;

(454) 3-(5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)propanol;

(455) 5-(3,5-Dichlorophenylthio)-4-isopropyl-2-N-methylaminomethyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(456) 5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-2-methanesulfonamido-1H-imidazole;

(457) 2-Carbamoyloxymethyl-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(458) 2-(1-n-Butyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(459) 2-(5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(460) 5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylacetonitrile;

(461) 4-Isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-2-freedomites-1H-imidazole;

(462) 2-(5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(463) 2-(1-(4-Aminobenzyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(464) 2-Diaminomethylene-4-isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole;

(465) 2-(5-(3-Chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ylethoxy)ethyl acetate;

(466) 1-Ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazol-2-ylacetonitrile;

(467) 2-(5-(3-Nitrophenylthio)-lenity)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(469) 4-Isopropyl-2-N-methyl(thiocarbamoyl)oxymethyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazole;

(470) 5-(3,5-Dichlorophenylthio)-1-vermeil-4-isopropyl-1H-imidazol-2-ylmethanol;

(471) 2-(5-(3-Nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ylethoxy)ethyl acetate;

(472) 2-Diaminomethylene-4-isopropyl-5-(3-forfinally)-1-pyridin-3-ylmethyl)-1H-imidazole;

(473) 5-(3,5-Differenlty)-4-isopropyl-2-N-methyl(thiocarbamoyl)oxymethyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(474) 1-(3-Aminobenzyl)-2-carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(475) 2-(2-Azidoethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(476) 2-Carbamoyloxymethyl-1-cyclopropylmethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(477) 1-n-Butyl-2-(2-carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(478) 5-(3,5-Differenlty)-4-isopropyl-1-(2-methylpyridin-3-ylmethyl)-1H-imidazol-2-ylmethanol;

(479) 1-Ethyl-4-isopropyl-5-phenylthio-1H-imidazole-2-carbaldehyde;

(480) 2-(5-Isopropyl-1-methyl-4-(3-forfinally)-1H-imidazol-2-ylethoxy)ethanol;

(481) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazole;

(482) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ilmatieteen;

(485) 5-(3-Chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde;

(486) 2-Acetamidomethyl-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(487) 1-(4-Aminobenzyl)-5-(3,5-dichlorophenylthio)-2-(3-carbamoyloximes)-4-isopropyl-1H-imidazole;

(488) 2-(1-Ethyl-5-isopropyl-4-phenylthio-1H-imidazol-2-ylethoxy)ethanol;

(489) 2-Dimethylaminomethyl-4-isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazole;

(490) 5-(3-Chlorophenylthio)-1-ethyl-4-isopropyl-2-N-methyl(thiocarbamoyl)oxymethyl-1H-imidazole;

(491) 2-(5-(3,5-Differenlty)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanol;

(492) 2-(4-(3,5-Dichlorophenylthio)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(493) 4-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(494) 2-(2-amino-ethyl)-5-(3-nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(495) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-(2-(pyridin-4-yl)ethyl)-1H-imidazole;

(496) 2-Aminomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(497) 4-Isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylacetonitrile;

(498) 2-Azidomethyl-5-isopropyl-4-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole;

(499) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-2-azole;

(501) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoyloximes)-methyl-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(502) 2-(5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylethoxy)ethyl acetate;

(503) 2-(5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylethoxy)ethyl acetate;

(504) 5-(3-chlorophenylthio)-2-diaminomethylene-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(505) 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-n-propyl-1H-imidazol-2-yl)ethanol;

(506) 4-Isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazole-2-carbaldehyde the oxime;

(507) 2-(1-(3-Aminobenzyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(508) 1-Allyl-2-carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(509) 5-(3-Chlorophenylthio)-2-diaminomethylene-4-isopropyl-1-methyl-1H-imidazole;

(510) 2-Carbamoyloxymethyl-4-isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole;

(511) 5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylacetic;

(512) 2-(2-Azidoethyl)-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(513) 2-(4-Isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(514) 5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-1,4-aminobutiramida-1H-imidazole;

l-1-methyl-4-phenylthio-1H-imidazole-2-carbaldehyde;

(517) 2-(5-(3,5-Differenlty)-4-isopropyl-1-(3-phenylpropyl)-1H-imidazol-2-yl)ethanol;

(518) 2-(2-Azidoethyl)-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(519) N-(5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-4-ylmethyl)acetamide;

(520) 2-(5-(3,5-Differenlty)-1-vermeil-4-isopropyl-1H-imidazol-2-yl)ethanol;

(521) 2-Acetamidomethyl-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(522) 2-Carbamoyloxymethyl-5-(3-chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(523) 1-Benzyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-ylmethanol;

(524) 1-Cyclopropylmethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-ylmethanol;

(525) 5-(3,5-Dichlorophenylthio)-4-isopropyl-2-N-methylcarbamoylmethyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(526) 2-(5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(527) 2-Carbamoyloxymethyl-4-(3,5-dimethylphenyl)-5-isopropyl-1-methyl-1H-imidazole;

(528) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole-2-carbaldehyde the oxime;

(529) 2-Carbamoyloxymethyl-4-(3,5-differenlty)-1-ethyl-5-isopropyl-1H-imidazole;

(530) 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazol-2-yl)ethanol;

(531) 5-(3,5-Diptotes)-1H-imidazol-2-yl)propanol;

(533) 2-(2-Carbamoylethyl)-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(534) 2-(3-Carbamoyloximes)-1-ethyl-4-isopropyl-5-phenylthio-1H-imidazole;

(535) Methyl 3-(5-(3,5-differenlty)-4-isopropyl-1-methyl-1H-imidazol-2-yl)propionate;

(536) 2-(4-Isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)ethanol;

(537) 1-Ethyl-4-isopropyl-5-phenylthio-1H-imidazol-2-ylacetic;

(538) 3-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-yl)propanol;

(539) 2-(3-Carbamoyloximes)-4-isopropyl-1-methyl-5-phenylthio-1H-imidazole;

(540) 2-Carbamoyloxymethyl-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(541) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylacetonitrile;

(542) N-(5-(3-Nitrophenylthio)-4-isopropyl-1-methyl-1H-imidazol-4-ylmethyl)acetamide;

(543) 2-Azidomethyl-4-(3,5-dichlorophenylthio)-1-ethyl-5-isopropyl-1H-imidazole;

(544) 5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole-2-carbaldehyde the oxime;

(545) 4-(3,5-Dimethylphenyl)-1-ethyl-5-isopropyl-1H-imidazol-2-ylmethanol;

(546) 4-(3,5-Differenlty)-5-isopropyl-1-methyl-1H-imidazol-2-ilmatieteen;

(547) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ilmatieteen;

(548) 2-(propyl-2-methanesulfonamido-1-(pyridine-2-ylmethyl)-1H-imidazole;

(550) 2-Carbamoyloxymethyl-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(551) 4-Isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole-2-carbaldehyde;

(552) 4-(3,5-Dichlorophenylthio)-5-isopropyl-1-methyl-1H-imidazol-2-ylmethanol;

(553) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylacetic;

(554) 1-(2-Aminobenzyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-2-ylmethanol;

(555) 2-(3-Carbamoylmethyl)-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(556) 2-Azidomethyl-5-isopropyl-1-methyl-4-(3-forfinally)-1H-imidazole;

(557) 1-Benzyl-2-carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(558) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1-n-propyl-1H-imidazole;

(559) 3-(1-Ethyl-4-isopropyl-5-phenylthio-1H-imidazol-2-yl)-propanol;

(560) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole-2-carbaldehyde the oxime;

(561) 2-Carbamoyloxymethyl-5-(3,5-dimethylphenyl)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(562) 2-Carbamoyloxymethyl-4-isopropyl-1-methyl-5-(3-forfinally)-1H-imidazole;

(563) 2-2-(Acetoxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(564) 3-(1,5-Dibenzyl-4-isopropyl-1H-imidazol-2-yl)propanolamide)-1-vermeil-5-isopropyl-1H-imidazol-2-ylmethanol;

(567) 4-(3-Nitrophenylthio)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole-2-carbaldehyde;

(568) 5-(3-Nitrophenylthio)-4-isopropyl-2-N-methylaminomethyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(569) 4-(3,5-Differenlty)-5-isopropyl-1-methyl-1H-imidazol-2-ylmethanol;

(570) 2-(5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)ethanol;

(571) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1-(3-phenylpropyl)-1H-imidazole;

(572) 2-(2-Carbamoyloximes)methyl-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridyl-3-ylmethyl)-1H-imidazole;

(573) 2-(5-(3,5-Differenlty)-4-isopropyl-1-(2(1H)-pyridone-5-ylmethyl)-1H-imidazol-2-yl)ethanol;

(574) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(575) 5-(3,5-Differenlty)-4-isopropyl-2-N-methylaminomethyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(576) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylacetic;

(577) 3-(5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)propanol;

(578) 2-2-(Acetoxyethyl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(579) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylmethanol;

(580) 2-(2-Azidoethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-2-elmet the (582) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(583) 5-(3-Nitrophenylthio)-4-isopropyl-2-N-methylcarbamoylmethyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(584) 5-(3,5-Dichlorophenylthio)-2-(3-carbamoyloximes)-1-cyclopropylmethyl-4-isopropyl-1H-imidazole;

(585) 2-(1,4-Aminobutiramida-5-(3,5-differenlty)-1H-imidazol-2-yl)ethanol;

(586) 2-Azidomethyl-5-(3-chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(587) 5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylmethanol;

(588) 5-Isopropyl-4-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylmethanol;

(589) 1-(2-(2-Hydroxyethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(590) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-1-hexyl-4-isopropyl-1H-imidazole;

(591) 2-Diaminomethylene-5-(3-nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(592) 2-Acetamidomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(593) 2-Diaminomethylene-5-(3,5-differenlty)-1-ethyl-4-isopropyl-1H-imidazole;

(594) 4-Isopropyl-1-methyl-5-(3-forfinally)-1H-imidazol-2-ilmatieteen;

(595) 5-(3,5-Differenlty)-1-ethyl-4-isopropyl-2-methanesulfonamido-1H-imidazole;

(596) 2-Diaminomethylene-4-isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazole;

(597) 2-(3-Carbamoylmethyl)-5-(3-the l-1H-imidazole;

(599) 2-2-(Acetoxyethyl)-5-(3-chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(600) 2-Aminomethyl-4-isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazole;

(601) 2-Aminomethyl-1-ethyl-4-isopropyl-5-phenylthio-1H-imidazole;

(602) 4-Isopropyl-2-methanesulfonamido-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole;

(603) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1-(3-phenylpropyl)-1H-imidazole;

(604) 1-(2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(605) 3-(4-Isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)propanol;

(606) 3-(1-Cyclopropylmethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)propanol;

(607) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylmethanol;

(608) 2-(2-Carbamoylethyl)-5-(3-chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(609) 5-(3-Nitrophenylthio)-4-isopropyl-1-methyl)-1H-imidazole-2-carbaldehyde the oxime;

(610) 1-Ethyl-4-isopropyl-2-N-methylthiocarbamate-5-(3-forfinally)-1H-imidazole;

(611) 2-(5-(3,5-Differenlty)-4-isopropyl-1-(quinoline-3-ylmethyl)-1H-imidazol-2-yl)ethanol;

(612) 1-(5-(3,5-Dimethylphenyl)-2-(3-hydroxypropyl)-4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(613) 2-(5-(3,5-Dimethylphenyl)-4-isopropyl-1-(the azole-2-yl)propanol;

(615) 2-(5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(616) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ilmatieteen;

(617) 5-(3-Nitrophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ylacetic;

(618) 5-(3,5-Dimethylphenyl)-1-hexyl-4-isopropyl-1H-imidazol-2-ylmethanol;

(619) 5-Isopropyl-4-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole-2-carbaldehyde;

(620) Methyl-3-(5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)propionate;

(621) 4-(3-Chlorophenylthio)-5-isopropyl-1-methyl-1H-imidazol-2-ylmethanol;

(622) 2-Aminomethyl-5-(3-nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(623) 5-(3,5-Differenlty)-4-isopropyl-2-N-methylcarbamoylmethyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(624) 2-(5-(3-Nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ylethoxy)ethanol;

(625) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(626) 5-(3-Nitrophenylthio)-4-isopropyl-2-methanesulfonamido-1-(pyridine-3-ylmethyl)-1H-imidazole;

(627) 3-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(3-phenylpropyl)-1H-imidazol-2-yl)propanol;

(628) 2-(5-(3-Chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanol;

(629) 2-(2-amino-ethyl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1>(631) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-1,4-aminobutiramida-1H-imidazole;

(632) 2-Aminomethyl-4-(3,5-dichlorophenylthio)-5-isopropyl-1-methyl-1H-imidazole;

(633) 1-Allyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-ylmethanol;

(634) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-n-propyl-1H-imidazole;

(635) 2-Azidomethyl-5-(3,5-differenlty)-1-ethyl-4-isopropyl-1H-imidazole;

(636) 2-Diaminomethylene-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(637) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1-(2-(pyridin-4-yl)ethyl)-1H-imidazole;

(638) 1-(4-Aminobenzyl)-2-(3-carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(639) 2-Aminomethyl-5-isopropyl-4-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole;

(640) 5-(3,5-Differenlty)-4-isopropyl-1-n-propyl-1H-imidazol-2-ylmethanol;

(641) 2-(2-Acetoxyethyl)-5-(3-nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(642) 2-(2-Carbamoylethyl)-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(643) 3-(5-(3-Chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)propanol;

(644) 5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-2-freedomites-1H-imidazole;

(645) 4-Isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazole-2-carbaldehyde hydrazone;

(648) N-(5-(3-Nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazole-4-ylmethyl)acetamide;

(649) 5-(3-Nitrophenylthio)-1-ethyl-4-isopropyl-2-N-methylaminomethyl-1H-imidazole;

(650) 2-(3-Carbamoyloximes)-4-isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazole;

(651) Methyl-3-(4-isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazol-2-yl)propionate;

(652) 5-(3-Chlorophenylthio)-4-isopropyl-1-methyl-2-N-methylcarbamoylmethyl-1H-imidazole;

(653) 2-(2-Carbamoylethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(654) - alpha-(5-(3,5-Dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(655) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1-(3-(pyridin-4-yl)propyl)-1H-imidazole;

(656) 2-(2-amino-ethyl)-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(657) 2-Dimethylaminomethyl-4-isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole;

(658) 3-(1-Ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazol-2-yl)propanol;

(659) 4-Isopropyl-2-methanesulfonamido-1-methyl-5-phenylthio-1H-imidazole;

(660) 1-Allyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazol-2-ylmethanol;

(661) 2-(2-Carbamoylethyl)-1,5-dibenzyl-4-isopropyl-1H-imidazole;

(662) 4-Isopropyl-2-N-methylaminomethyl-5-phenylthio-1-(feast of the Sabbath.>/BR>(664) 2-(2-Azidoethyl)-4-isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazole;

(665) 4-Isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole-2-carbaldehyde the oxime;

(666) 3-(5-(3,5-Differenlty)-1-vermeil-4-isopropyl-1H-imidazol-2-yl)propanol;

(667) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1-(2-phenylethyl)-1H-imidazole;

(668) 1-n-Butyl-2-(2-carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(669) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(670) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-1-ethyl-4-isopropyl-1H-imidazole;

(671) 2-(3-Carbamoylmethyl)-5-(3-chlorinity)-4-isopropyl-1-methyl-1H-imidazole;

(672) 2-(2-Carbamoyloximes)methyl-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(673) 2-Diaminomethylene-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(674) 2-(4-Isopropyl-1-methyl-5-(3-forfinally)-1H-imidazol-2-ylethoxy)ethanol;

(675) 3-(5-(3,5-Dimethylphenyl)-1-vermeil-4-isopropyl-1H-imidazol-2-yl)propanol;

(676) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(2-phenylethyl)-1H-imidazol-2-ylmethanol;

(677) 1-Ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazol-2-ylacetic;

(678) 2-(2-Carbamoylethyl)-5-(3,5-dipyridine-4-ylmethyl)-1H-imidazole;

(680) 4-Isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ilmatieteen;

(681) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-methyl-1H-imidazole;

(682) 4-(3-Chlorophenylthio)-5-isopropyl-1-methyl-1H-imidazol-2-ilmatieteen;

(683) 2-(2-Azidoethyl)-4-isopropyl-5-(phenylthio-1-(pyridine - 4-ylmethyl)-1H-imidazole;

(684) 2-(2-Azidoethyl)-4-isopropyl-1-methyl-5-phenylthio-1H-imidazole;

(685) 1-Ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazol-2-ilmatieteen;

(686) 2-(3-Carbamoyloximes)-1-cyclopropylmethyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazole;

(687) 4-Isopropyl-2-N-methylaminomethyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazole;

(688) Methyl 3-(4-isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazol-2-yl)propionate;

(689) 2-Diaminomethylene-5-(3-nitrophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(690) 1,4-Aminobutiramida-5-(3,5-dimethylphenyl)-1H-imidazol-2-ylmethanol;

(691) 2-(3-Carbamoyloximes)-4-isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazole;

(692) 2-Azidomethyl-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(693) 1-Ethyl-4-isopropyl-2-N-methylthiocarbamate-5-phenylthio-1H-imidazole;

(694) 2-(5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-yl)ethanol;

(6 is)-4-isopropyl-1-methyl-1H-imidazol-2-yl)propionate;

(697) 2-(2-Acetoxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(698) 2-2-(Acetoxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(699) 2-Azidomethyl-4-(3-chlorophenylthio)-1-ethyl-5-isopropyl-1H-imidazole;

(700) 3-(5-(3,5-Differenlty)-4-isopropyl-1-(2-phenylethyl)-1H-imidazol-2-yl)propanol;

(701) 2-(1-n-Butyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(702) 1-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-ylmethanol;

(703) -(2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(704) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole-2-carbaldehyde;

(705) 5-(3,5-Dichlorophenylthio)-2-diaminomethylene-1-ethyl-4-isopropyl-1H-imidazole;

(706) 2-(5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ylethoxy)ethanol;

(707) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(3-phenylpropyl)-1H-imidazol-2-ylmethanol;

(708) 2-(2-amino-ethyl)-4-isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazole;

(709) 2-Carbamoylmethyl-5-(3,5-dimethylphenyl)-4-isopropyl-1-n-propyl-1H-imidazole;

(710) 5-(3,5-Dichlorophenylthio)-2-(3-carbamoyloximes)-1,4-aminobutiramida-1H-imidazole;

(711) 1-(2-Aminobenzyl)-5-(3,5-dichlorophenylthio)-2-(3-carbamoyloximes)-4-from the 2-(3-Carbamoylmethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazole;

(714) 2-Carbamoyloxymethyl-5-(3-nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(715) 2-Azidomethyl-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(716) 3-(5-(3,5-Differenlty)-1-hexyl-4-isopropyl-1H-imidazol-2-yl)propanol;

(717) 2-(5-(3-Nitrophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanol;

(718) 1-Benzyl-2-(3-carbamoylmethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazole;

(719) 5-(3-Chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ylacetonitrile;

(720) 2-(5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)ethanol;

(721) 2-(4-(3,5-Dichlorophenylthio)-1-ethyl-5-isopropyl-1H-imidazol-2-ylethoxy)ethanol;

(722) 4-Isopropyl-2-N-methylaminomethyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazole;

(723) 4-Isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazole-2-carbaldehyde;

(724) 5-(3-Nitrophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ylmethanol;

(725) 5-(3,5-Dichlorophenylthio)-1-n-butyl-2-carbamoyloxymethyl-4-isopropyl-1H-imidazole;

(726) 5-(3,5-Differenlty)-1-ethyl-4-isopropyl-2-N-methylcarbamoylmethyl-1H-imidazole;

(727) 2-Dimethylaminomethyl-4-isopropyl-1-methyl-5-phenylthio-1H-imidazole;

(728) 2-Carbamoyloxymethyl-1-ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazole;

(729) 5-(3,5-Differentiel-1-(pyridine-4-ylmethyl)-1H-imidazol-2-yl)ethanol;

(731) 2-Carbamoyloxymethyl-5-(3,5-dimethylphenyl)-4-isopropyl-1-methyl-1H-imidazole;

(732) 2-(2-amino-ethyl)-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(733) 2-(3-Carbamoyloximes)-4-isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole;

(734) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1-methyl-1H-imidazole;

(735) 2-Acetamidomethyl-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(736) 2-(1-Allyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(737) 5-(3,5-Dichlorophenylthio)-2-(3-carbamoyloximes)-4-isopropyl-1-(3-(pyridin-4-yl)propyl)-1H-imidazole;

(738) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylacetic;

(739) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(740) 1-Benzyl-2-(3-carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(741) 4-Isopropyl-2-N-methyl(thiocarbamoyl)oxymethyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole;

(742) 3-(5-(3,5-Dichlorophenylthio)-1,4-aminobutiramida-1H-imidazol-2-yl)propanol;

(743) 2-(2-Azidoethyl)-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(744) 2-(2-Carbamoyloximes)methyl-4-isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-they are the Il-4-(3,5-differenlty)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(747) 2-(3-Carbamoylmethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(748) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-(quinoline-3-ylmethyl)-1H-imidazole;

(749) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylmethanol;

(750) Methyl-3-(4-isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazol-2-yl)propionate;

(751) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoyloximes)-methyl-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(752) 5-(3,5-Differenlty)-4-isopropyl-2 - methanesulfonamido-1-(pyridine-4-ylmethyl)-1H-imidazole;

(753) 2-(2-Carbamoyloximes)methyl-4-isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazole;

(754) 4-(3,5-Dichlorophenylthio)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylmethanol;

(755) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-2-freedomites-1H-imidazole;

(756) 5-(3,5-Dichlorophenylthio)-1-n-butyl-2-(3-carbamoyloximes)-4-isopropyl-1H-imidazole;

(757) 2-Aminomethyl-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(758) 2-Aminomethyl-4-(3-chlorophenylthio)-1-ethyl-5-isopropyl-1H-imidazole;

(759) 4-(3,5-Dichlorophenylthio)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ilmatieteen;

(760) 2-(2-amino-ethyl)-4-isopropyl-1-methyl-5-(3-BR>
(762) 4-(3-Nitrophenylthio)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylmethanol;

(763) 4-Isopropyl-1-methyl-5-(3-forfinally)-1H-imidazole-2-carbaldehyde;

(764) 5-Isopropyl-1-methyl-4-(3-forfinally)-1H-imidazol-2 - ilmatieteen;

(765) 2-Aminomethyl-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(766) 2-(2-Azidoethyl)-4-isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazole;

(767) 1-n-Butyl-2-carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(768) 2-(2-acetoxyethyl)-1-ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazole;

(769) 4-(3,5-Differenlty)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylmethanol;

(770) 3-(5-(3,5-Differenlty)-4-isopropyl-1-(2-methylpyridin-3-ylmethyl)-1H-imidazol-2-yl)propanol;

(771) -(5-(3,5-Dichlorophenylthio)-2-(3-hydroxypropyl)-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(772) 4-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-1-vermeil-5-isopropyl-1H-imidazole;

(773) 3-(5-(3,5-Differenlty)-4-isopropyl-1-(quinoline-3-ylmethyl)-1H-imidazol-2-yl)propanol;

(774) 2-(1-Cyclopropylmethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(775) 5-(3,5-Differenlty)-4-isopropyl-1-(3-(pyridin-4-yl)propyl)-1H-imidazol-2-ylmethanol;

(776) 5-(3-Chlorophenylthio)-4-isopropyl-1-methyl-1H-imida is;

(778) 5-(3-Chlorophenylthio)-4-isopropyl-1-methyl-2-N-methylaminomethyl-1H-imidazole;

(779) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-(2-methylpyridin-3-ylmethyl)-1H-imidazole;

(780) 5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole-2-carbaldehyde the oxime;

(781) 2-(1-Cyclopropylmethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(782) 2-Dimethylaminomethyl-1-ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazole;

(783) 2-Aminomethyl-5-(3,5-differenlty)-1-ethyl-4-isopropyl-1H-imidazole;

(784) 1-Allyl-2-(3-carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol;

(785) 2-Acetamidomethyl-4-isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazole;

(786) 5-(3,5-Dichlorophenylthio)-2-(3-carbamoyloximes)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(787) 3-(5-(3,5-Differenlty)-4-isopropyl-1-methyl-1H-imidazol-2-yl)propanol;

(788) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazole;

(789) 1-Ethyl-4-isopropyl-5-phenylthio-1H-imidazole-2-carbaldehyde the oxime;

(790) Methyl-3-(5-(3,5-differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-yl)propionate;

(791) 2-(5-Isopropyl-4-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(792) 5-(3,5-Dichlorophenylthio)-2-dim the si)ethanol;

(794) 2-(2-Carbamoyloximes)methyl-4-isopropyl-1-methyl-5-phenylthio-1H-imidazole;

(795) 4-Isopropyl-2-methanesulfonamido-1-methyl-5-(3-forfinally)-1H-imidazole;

(796) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(6-oxo-1,6-dihydropyridines-3-yl)methyl-1H-imidazol-2-ylmethanol;

(797) 1-n-Butyl-2-carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(798) 3-(1-(2-Aminobenzyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-2-yl)propanol;

(799) 5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ylacetonitrile;

(800) 4-Isopropyl-1-methyl-5-(3-forfinally)-2-freedomites-1H-imidazole;

(801) 2-(2-Carbamoylethyl)-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(802) 1-Benzyl-2-carbamoyloxymethyl-4-(3,5-differenlty)-5-isopropyl-1H-imidazole;

(803) 5-(3,5-Differenlty)-1-ethyl-4-isopropyl-1H-imidazole-2-carbaldehyde the oxime;

(804) 5-(3,5-Differenlty)-1-ethyl-4-isopropyl-2-freedomites-1H-imidazole;

(805) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoyloximes)-methyl-1-ethyl-4-isopropyl-1H-imidazole;

(806) 5-(3,5-Dimethylphenyl)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylmethanol;

(807) N-(5-(3,5-Differenlty)-4-isopropyl-1-methyl-1H-imidazol-4-ylmethyl)acetamide;

(808) -(5-(3,5-Dimethylphenyl)-2-(3-hydroxypropyl)- 2-2-(Acetoxyethyl)-5-(3,5-differenlty)-1-ethyl-4-isopropyl-1H-imidazole;

(811) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1-n-propyl-1H-imidazole;

(812) 5-(3,5-Dichlorophenylthio)-2-(3-carbamoyloximes)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(813) 2-(2-amino-ethyl)-4-(3-chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(814) 2-Carbamoyloxymethyl-1,4-dibenzyl-5-isopropyl-1H-imidazole;

(815) 5-(3,5-Dichlorophenylthio)-2-(3-carbamoyloximes)-4-isopropyl-1-n-propyl-1H-imidazole;

(816) 1-(5-(3,5-Differenlty)-2-hydroxymethyl-4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(817) 2-Azidomethyl-5-isopropyl-1-methyl-4-phenylthio-1H-imidazole;

(818) 5-(3,5-Differenlty)-1-hexyl-4-isopropyl-1H-imidazol-2-ylmethanol;

(819) 2-Acetamidomethyl-5-(3-chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(820) 4-(3,5-Dichlorophenylthio)-1-ethyl-5-isopropyl-1H-imidazol-2-ilmatieteen;

(821) 2-Carbamoyloxymethyl-4-(3,5-differenlty)-1-vermeil-5-isopropyl-1H-imidazole;

(822) 1-Ethyl-4-isopropyl-5-phenylthio-1H-imidazol-2-ilmatieteen;

(823) 2-(5-(3-Chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)ethanol;

(824) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(2-methylpyridin-3-ylmethyl)-1H-imidazol-2-ylmethanol;

(825) 5-Isopropyl-1-methyl-4-phenylthio-1H-imidazol-2-ilmatieteen;

(826) 2-Acetamidomethyl-5-(3-nitrophenylthio)-4-isopropyl-28) 1-(2-Carbamoylethyl)-2-carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(829) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-1-cyclopropylmethyl-4-isopropyl-1H-imidazole;

(830) 2-(2-Carbamoylethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(831) 2-(5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylethoxy)ethyl acetate;

(832) Methyl 3-(1-ethyl-4-isopropyl-5-(phenylthio-1H-imidazol-2-yl)propionate;

(833) 2-(5-(3,5-Differenlty)-1-ethyl-4-isopropyl-1H-imidazol-2-ylethoxy)ethyl acetate;

(834) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(835) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1-(2-methylpyridin-3-ylmethyl)-1H-imidazole;

(836) 4-Isopropyl-1-methyl-5-phenylthio-1H-imidazole-2-carbaldehyde;

(837) 2-(3-Carbamoylmethyl)-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(838) 4-Isopropyl-2-methanesulfonamido-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole;

(839) 2-2-(Acetoxyethyl)-4-isopropyl-1-methyl-5-phenylthio-1H-imidazole;

(840) 2-(5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylethoxy)ethyl acetate;

(841) N-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-4-ylmethyl)acetamide;

(842) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-2-ur (844) 5-(3-Nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazole-2-carbaldehyde the oxime;

(845) 5-(3-Nitrophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ylacetonitrile;

(846) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-2-freedomites-1H-imidazole;

(847) 2-(2-Azidoethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(848) 2-Aminomethyl-4-(3,5-differenlty)-1-ethyl-5-isopropyl-1H-imidazole;

(849) 4-(3-Nitrophenylthio)-1-ethyl-5-isopropyl-1H-imidazol-2-ilmatieteen;

(850) 3-(5-(3,5-Divertenti-4-isopropyl-1-pyridin-4-ylmethyl)-1H-imidazol-2-yl)propanol;

(851) 2-Diaminomethylene-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(852) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-carbaldehyde hydrazone;

(853) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazole-2-carbaldehyde hydrazone;

(854) 2-(5-(3,5-Differenlty)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazol-2-yl)ethanol;

(855) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1-n-propyl-1H-imidazole;

(856) 5-(3,5-Differenlty)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde the oxime;

(857) 3-(5-(3,5-Differenlty)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazol-2-yl)propanol;

(858) 2-Azidomethyl-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(859) 1-Ethyl-5-isopropy the BR>
(861) 5-(3-Nitrophenylthio)-4-isopropyl-1-methyl-2-N-methyl(thiocarbamoyl)oxymethyl-1H-imidazole;

(862) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole-2-carbaldehyde;

(863) 5-(3-nitrophenylthio)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde hydrazone;

(864) 2-(2-Azidoethyl)-5-(3-chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(865) 2-Azidomethyl-5-(3,5-differenlty)-4-isopropyl-1-methyl-1H-imidazole;

(866) 2-(2-amino-ethyl)-5-(3,5-differenlty)-1-ethyl-4-isopropyl-1H-imidazole;

(867) 2-(4-(3-Nitrophenylthio)-5-isopropyl-1-methyl-1H-imidazol-2-ylethoxy)ethanol;

(868) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1-(quinoline-3-ylmethyl)-1H-imidazole;

(869) 2-Azidomethyl-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(870) 5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-1-hexyl-4-isopropyl-1H-imidazole;

(871) 5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazole;

(872) 3-(5-(3,5-Dimethylphenyl)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)propanol;

(873) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-1,4-aminobutiramida-1H-imidazole;

(874) Methyl 3-(5-(3,5-dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)propionate;

(875) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-1-R>
(877) N-(5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-4-ylmethyl)acetamide;

(878) 2-(2-Acetoxyethyl)-4-isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazole;

(879) 1-Ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazole-2-carbaldehyde the oxime;

(880) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazole-2-carbaldehyde the oxime;

(881) 2-Carbamoyloxymethyl-5-isopropyl-4-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole;

(882) 2-Aminomethyl-4-(3-nitrophenylthio)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(883) 4-Isopropyl-2-N-methylaminomethyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazole;

(884) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole-2-carbaldehyde hydrazone;

(885) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ilmatieteen;

(886) N-(4-Isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazol-4-ylmethyl)acetamide;

(887) 5-(3,5-Differenlty)-4-isopropyl-1-(quinoline-3-ylmethyl)-1H-imidazol-2-ylmethanol;

(888) 5-(3-Nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ylacetonitrile;

(889) 4-(3,5-Dimethylphenyl)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylmethanol;

(890) 1-n-Butyl-2-(2-carbamoylmethyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazole;

(891) 5-(3-Chlorophenylthio)-4-isopr-imidazole-2-carbaldehyde hydrazone;

(893) 5-(3-Chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole-2-carbaldehyde hydrazone;

(894) 1-Ethyl-4-isopropyl-2-N-methylaminomethyl-5-(3-forfinally)-1H-imidazole;

(895) 2-Azidomethyl-1-ethyl-5-isopropyl-4-phenylthio-1H-imidazole;

(896) 5-(3,5-(Differentia)-4-isopropyl-2-N-methylaminomethyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(897) 2-(3-Carbamoylmethyl)-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(898) 2-(1-(2-Aminobenzyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(899) 2-(2-Carbamoyloximes)methyl-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(900) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylmethanol;

(901) 5-Isopropyl-4-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylmethanol;

(902) 2-(2-amino-ethyl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(903) 1-Ethyl-4-isopropyl-5-phenylthio)-1H-imidazole-2-carbaldehyde hydrazone;

(904) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylmethanol;

(905) 3-(5-(3,5-Dimethylphenyl)-4-isopropyl-1-n-propyl-1H-imidazol-2-yl)propanol;

(906) 1-(2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-1-yl)-2-propanone; 1 (907) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoyloximes)metl)propanol;

(909) 2-(5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-yl)ethanol;

(910) 1-(5-(3,5-Differenlty)-2-(3-hydroxypropyl)-4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(911) 2-(5-(3,5-Dichlorophenylthio)-1-cyclopropylmethyl-4-isopropyl-1H-imidazol-2-yl)ethanol;

(912) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylmethanol;

(913) 2-(2-Acetoxyethyl)-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(914) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylmethanol;

(915) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylmethanol;

(916) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-(6-oxo-1,6-dihydropyridines-3-yl)methyl-1H-imidazole;

(917) 2-Carbamoyloxymethyl-1,5-dibenzyl-4-isopropyl-1H-imidazole;

(918) 2-(1-Cyclopropylmethyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(919) 5-(3-Chlorophenylthio)-4-isopropyl-2-N-methylaminomethyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(920) 3-(5-Chlorophenylthio)-4-isopropyl-2-methanesulfonamido-1-(pyridine-4-ylmethyl)-1H-imidazole;

(921) Methyl-3-(5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1-h-imidazol-2-yl)propionate;

(922) 3-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-yl)Pro) 2-(4-Isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylethoxy)ethyl acetate;

(925) 5-(3-Nitrophenylthio)-4-isopropyl-1-methyl-1H - imidazol-2-ilmatieteen;

(926) 2-(2-Acetoxyethyl)-5-(3-nitrophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(927) 3-(1,4-Aminobutiramida-5-(3,5-dimethylphenyl)-1H-imidazol-2-yl)propanol;

(928) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole-2-carbaldehyde;

(929) 2-Aminomethyl-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(930) 1-Allyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-2-ylmethanol;

(931) 5-(3,5-Dichlorophenylthio)-4-isopropyl-2-methanesulfonamido-1-(pyridine-3-ylmethyl)-1H-imidazole;

(932) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-n-propyl-1H-imidazole;

(933) 5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-4-isopropyl-1-(3-(pyridin-4-yl)propyl-1H-imidazole;

(934) 2-(3-Carbamoylmethyl-5-(3,5-differenlty)-4-isopropyl-1-(quinoline-3-ylmethyl)-1H-imidazole;

(935) 2-(5-(3,5-Dichlorophenylthio)-1-n-butyl-4-isopropyl-1H-imidazol-2-yl)ethanol;

(936) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde;

(937) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-1-ethyl-4-isopropyl-1H-imidazole;

(938) 3-(5-(3,5-Dimethylphenyl)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)propanol;

(939) 5-(3,5-Differenlty)-4-isopropyl-1-(2-(pyridin-4-yl)ethyl)-1H-misoprotol-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(942) 4-Isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylacetic;

(943) 5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-4-isopropyl-1-(6-oxo-1,6-dihydropyridines-3-yl)methyl-1H-imidazole;

(944) 2-(2-Carbamoylethyl)-4-isopropyl-1-methyl-5-phenylthio-1H-imidazole;

(945) 2-Dimethylaminomethyl-4-isopropyl-1-methyl-5-(3-forfinally)-1H-imidazole;

(946) 4-(3,5-Differenlty)-1-ethyl-5-isopropyl-1H-imidazol-2-ylmethanol;

(947) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-1-hexyl-4-isopropyl-1H-imidazole;

(948) 5-(3,5-Differenlty)-4-isopropyl-1-(2-(1H)-pyridone-5-ylmethyl)-1H-imidazol-2-ylmethanol;

(949) 2-(2-amino-ethyl)-4-isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazole;

(950) 5-(3-Chlorophenylthio)-1-ethyl-4-isopropyl-2-methanesulfonamido-1H-imidazole;

(951) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1-(6-oxo-1,6-dihydropyridines-3-yl)methyl-1H-imidazole;

(952) 5-(3-Chlorophenylthio)-4-isopropyl-1-methyl-2-N-methylcarbamoylmethyl-1H-imidazole;

(953) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylmethanol;

(954) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ylmethanol;

(955) -(5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(956) 1-Benzyl-5-(3,5-dimethylphenyl;

(958) 1-(5-(3,5-Dichlorophenylthio)-2-(3-hydroxypropyl)-4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(959)-5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ilmatieteen;

(960) 2-(4-Isopropyl-1-methyl-5-phenylthio-1H-imidazol-2-ylethoxy)ethyl acetate;

(961) 3-(5-3-Nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-yl)propanol;

(962) 2-Azidomethyl-4-isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazole;

(963) 5-(3,5-Differenlty)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazol-2-ylmethanol;

(964) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-1,4-aminobutiramida-1H-imidazole;

(965) 2-(2-amino-ethyl)-4-isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazole;

(966) 4-Isopropyl-2-N-methylthiocarbamate-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazole;

(967) 5-(3-Nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazole-2-carbaldehyde;

(968) 2-(5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylethoxy)ethyl acetate;

(969) 3-(5-(3-Nitrophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)propanol;

(970) -(2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(971) 2-Aminomethyl-5-(3,5-differenlty)-4-isopropyl-1-methyl-1H-imidazole;

(972) 2-(3-Carbamoylmethyl)-5-(3-chloro who ropyl-1H-imidazol-1-yl)acetophenone;

(974) 5-(3,5-Differenlty)-1-ethyl-4-isopropyl-2-N-methylaminomethyl-1H-imidazole;

(975) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazole-2-carbaldehyde the oxime;

(976) 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(2-methylpyridin-3-ylmethyl)-1H-imidazol-2-yl)ethanol;

(977) 2-(2-amino-ethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(978) 1-(2-Aminobenzyl)-2-(2-carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(979) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1-(quinoline-3-ylmethyl)-1H-imidazole;

(980) 3-(5-(3,5-Differenlty)-4-isopropyl-1-(3-phenylpropyl)-1H-imidazol-2-yl)propanol;

(981) 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylethoxy)ethyl acetate;

(982) 2-(2-Acetoxyethyl)-5-(3,5-dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(983) 3-(5-(3,5-Differenlty)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)propanol;

(984) -(2-(3-Carbamoylmethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(985) 2-Azidomethyl-4-(3,5-differenlty)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(986) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-1-hexyl-4-isopropyl-1H-imidazole;

(987) 1-(4-Aminobenzyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-2-ylmethanol;

(988) 2-(5-(3,5-Delamination-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(990) 2-(5-(3,5-Differenlty)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)ethanol;

(991) 5-(3-Nitrophenylthio)-4-isopropyl-2-N-methylthiocarbamate-1-(pyridine-4-ylmethyl)-1H-imidazole;

(992) 2-(3-Carbamoylmethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(993) 5-(3-Chlorophenylthio)-4-isopropyl-2-methanesulfonamido-1-methyl-1H-imidazole;

(994) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1-methyl-1H-imidazole;

(995) 2-Azidomethyl-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(996) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylmethanol;

(997) 5-(3-Chlorophenylthio)-4-isopropyl-1-methyl-2-freedomites-1H-imidazole;

(998) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1-(2-(pyridin-4-yl)ethyl)-1H-imidazole;

(999) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylacetonitrile;

(1000) 3-(1-Benzyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)propanol;

(1001) 5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole-2-carbaldehyde;

(1002) 2-Carbamoyloxymethyl-5-(3-nitrophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(1003) 4-(3-Nitrophenylthio)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ilmatieteen;

(1004) 2-(1,4-Aminobutiramida 5--3-ylmethyl)-1H-imidazole;

(1006) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ilmatieteen;

(1007) 2-(2-Carbamoylethyl)-4-isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1008) 5-(3-Nitrophenylthio)-1-ethyl-4-isopropyl-2-N-methyl-carbamoyloxymethyl-1H-imidazole;

(1009) 4-Isopropyl-1-methyl-5-(3-forfinally)-1H-imidazole-2-carbaldehyde the oxime;

(1010) 2-(2-Acetoxyethyl)-5-(3-chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(1011) -(5-(3,5-Differenlty)-2-(3-hydroxypropyl)-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(1012) 2-Aminomethyl-5-(3-chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(1013) 4-Isopropyl-2-N-methylcarbamoylmethyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1014) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole-2-carbaldehyde the oxime;

(1015) 4-Isopropyl-2-N-methyl(thiocarbamoyl)oxymethyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1016) 2-(5-(3,5-Dimethylphenyl)-1-hexyl-4-isopropyl-1H-imidazol-2-yl)ethanol;

(1017) 2-(5-(3-Chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ylethoxy)ethanol;

(1018) 3-(5-(3,5-Dimethylphenyl)-4-isopropyl-1-methyl-1H-imidazol-2-yl)propanol;

(1019) 2-Aminomethyl-1-ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazole;

(1020) 2-(2-Carbamoylethyl)-5-(3,5-differenl is rfinity)-1H-imidazole;

(1022) 1-Benzyl-4-(3,5-differenlty)-5-isopropyl-1H-imidazol-2-ylmethanol;

(1023) 1-Allyl-5-(3,5-dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1H-imidazole;

(1024) 5-(3,5-Differenlty)-2-dimethylaminomethyl-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1025) 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(2-methylpyridin-3-ylmethyl)-1H-imidazol-2-yl)ethanol;

(1026) 1-(2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(1027) 3-(4-Isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazol-2-yl)propanol;

(1028) 5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-1-ethyl-4-isopropyl-1H-imidazole;

(1029) 2-Carbamoyloxymethyl-5-isopropyl-4-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1030) 1-Allyl-5-(3,5-dichlorophenylthio)-2-carbamoyloxymethyl-4-isopropyl-1H-imidazole;

(1031) 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(1032) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-1-ethyl-4-isopropyl-1H-imidazole;

(1033) 2-(3-Carbamoylmethyl)-5-(3,5-dimethylphenyl)-1-hexyl-4-isopropyl-1H-imidazole;

(1034) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1035) 2-Aminomethyl-1-ethyl-5-isopropyl-4-phenylthio-1H-imidazole;

(1036) 2-Aminomethyl-5-ISO-imidazole;

(1038) 1-Benzyl-4-(3,5-differenlty)-5-isopropyl-1H-imidazol-2-ylmethanol;

(1039) 2-(5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(1040) 2-Carbamoyloxymethyl-1-ethyl-5-isopropyl-4-(3-forfinally)-1H-imidazole;

(1041)-(2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(1042) 2-Acetamidomethyl-4-isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1043) 2-(2-Carbamoyloximes)methyl-5-(3-chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(1044) 2-Acetamidomethyl-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1045) 2-(5-(3,5-Dimethylphenyl)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-yl)ethanol;

(1046) 5-(3,5-Differenlty)-4-isopropyl-2-N-methyl(thiocarbamoyl)oxymethyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1047) 3-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)propanol;

(1048) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1-(6-oxo-1,6-dihydropyridines-3-yl)methyl-1H-imidazole;

(1049) 5-(3-Nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ylacetic;

(1050) 2-(1-Allyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(1051) 2-(5-(3-Chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ylethoxy)ethyl acetate;

(1052)-4-(3--4-isopropyl-1H-imidazole;

(1054) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazole;

(1055) 2-(5-(3,5-Differenlty)-4-isopropyl-1-n-propyl-1H-imidazol-2-yl)ethanol;

(1056) 1-(3-Aminobenzyl)-5-(3,5-dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1H-imidazole;

(1057) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole-2-carbaldehyde;

(1058) 1-(2-Aminobenzyl)-5-(3,5-dichlorophenylthio)-2-carbamoyloxymethyl-4-isopropyl-1H-imidazole;

(1059) 3-(4-Isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazol-2-yl)propanol;

(1060) 1-Allyl-2-(2-carbamoylethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazole;

(1061) 5-(3-Chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ylacetonitrile;

(1062) 3-(5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-yl)propanol;

(1063) 2-Aminomethyl-5-(3,5-dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(1064) 3-(1-Allyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazol-2-yl)propanol;

(1065) Methyl 3-(5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-yl)propionate;

(1066) 2-(2-amino-ethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1067) 5-(3,5-Differenlty)-1-ethyl-4-isopropyl-1H-imidazol-2-ylacetic;

(1068) 5-(3-Chlorophenylthio)-1-ethyl-4-isopropyl-1H-aminopropyl-1-methyl-5-(3-forfinally)-1H-imidazol-2-yl)propionate;

(1071) 2-(2-Azidoethyl)-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1072) 3-(5-(3,5-Dimethylphenyl)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazol-2-yl)propanol;

(1073) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-2-freedomites-1H-imidazole;

(1074) 2-(5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(1075) 2-(5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylethoxy)ethyl acetate;

(1076) 2-(3-Carbamoyloximes)-4-isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1077) 2-Azidomethyl-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1078) 5-(3,5-Dimethylphenyl)-4-isopropyl-1-methyl-1H-imidazol-2-ylmethanol;

(1079) 2-Acetamidomethyl-4-isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1080) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole-2-carbaldehyde;

(1081) 3-(1-Allyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)propanol;

(1082) 5-(3,5-Differenlty)-2-dimethylaminomethyl-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1083) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ilmatieteen;

(1084) 4-Isopropyl-1-methyl-5-(3-forfinally)-1H-imidazol-2-ylmethanol;

(1085) 2-(5-(3-Harfe ropyl-1H-imidazol-2-yl)ethanol;

(1087) 5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-4-isopropyl-1-methyl-1H-imidazole;

(1088) 1-(5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(1089) 5-(3-Chlorophenylthio)-2-diaminomethylene-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1090) N-(5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-4-ylmethyl)acetamide;

(1091) Methyl 3-(5-(3-chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)propionate;

(1092) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylacetic;

(1093) 2-(2-Azidoethyl)-4-isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1094) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-1,4-aminobutiramida-1H-imidazole;

(1095) 2-Azidomethyl-4-(3,5-differenlty)-5-isopropyl-1-methyl-1H-imidazole;

(1096) 2-(2-amino-ethyl)-4-isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1097) 2-Azidomethyl-5-(3-nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(1098) 5-(3-Chlorophenylthio)-4-isopropyl-2-methanesulfonamido-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1099) 5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ilmatieteen;

(1100) 4-Isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylacetonitrile;

(1101) -(2-(3-Carbamoylmethyl)-5-(3,5-differentiator;

(1103) 2-(2-Carbamoyloximes)methyl-4-isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1104) 2-(2-amino-ethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1105) 5-(3,5-Dichlorophenylthio)-2-(3-carbamoyloximes)-4-isopropyl-1-(6-oxo-1,6-dihydropyridines-3-yl)methyl-1H-imidazole;

(1106) N-(5-(3-Chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-4-ylmethyl)acetamide;

(1107) 4-Isopropyl-2-N-methylaminomethyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1108) 2-Dimethylaminomethyl-4-isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1109) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1110) 1-Allyl-2-(2-carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(1111) 2-Azidomethyl-5-(3,5-dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(1112) 5-(3-Chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ylmethanol;

(1113) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-2-freedomites-1H-imidazole;

(1114) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1-(2-methylpyridin-3-ylmethyl)-1H-imidazole;

(1115)-4-Isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole-2-carbaldehyde hydrazone;

(1116) 2-(2-amino-ethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(PI

(1118) 1-Ethyl-5-isopropyl-4-phenylthio-1H-imidazol-2-ilmatieteen;

(1119) 2-(5-(3-Necromantia)-4-isopropyl-1-methyl-1H-imidazol-2-ylethoxy)ethyl acetate;

(1120) 2-(2-Azidoethyl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1121) N-(5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-4-ylmethyl)acetamide;

(1122) 5-Isopropyl-4-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole-2-carbaldehyde;

(1123) 3-(5-(3,5-Differenlty)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazol-2-yl)propanol;

(1124) 2-(2-Carbamoylethyl)-4-isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1125) 2-(1-Ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazol-2-ylethoxy)ethyl acetate;

(1126) 2-(5-(3-Chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ylethoxy)ethanol;

(1127) 5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1128) 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(2-(pyridin-4-yl)-1H-imidazol-2-yl)ethanol;

(1129) 2-(1-Allyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(1130) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1-(3-(pyridin-4-yl)propyl)-1H-imidazole;

(1131) 2-(3-Carbamoylmethyl)-5-(3,5-dimethylphenyl)-1-vermeil-4-isopropyl-1H-imidazole;

(1132) 5-(3-Harvel-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylmethanol;

(1134) 2-Acetamidomethyl-4-isopropyl-1-methyl-5-phenylthio-1H-imidazole;

(1135) 3-(5-(3,5-Differenlty)-4-isopropyl-1-n-propyl-1H-imidazol-2-yl)propanol;

(1136) 2-(2-Acetoxyethyl)-4-isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1137) 3-(1-(4-Aminobenzyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)propanol;

(1138) 5-(3-Nitrophenylthio)-2-dimethylaminomethyl-1-ethyl-4-isopropyl-1H-imidazole;

(1139) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-(3-(pyridin-4-yl)propyl)-1H-imidazole;

(1140) 2-(5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-yl)ethanol;

(1141) 5-(3,5-Differenlty)-1-ethyl-4-isopropyl-1H-imidazol-2-ylmethanol;

(1142) 4-Isopropyl-2-methanesulfonamido-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1143) 2-(1-Ethyl-4-isopropyl-5-phenylthio-1H-imidazol-2-ylethoxy)ethyl acetate;

(1144) 5-(3-Nitrophenylthio)-4-isopropyl-2-N-methyl(thiocarbamoyl)oxymethyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1145) 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-yl)ethanol;

(1146) 5-(3,5-Dichlorophenylthio)-4-isopropyl-2-methanesulfonamido-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1147) 2-2-(Acetoxyethyl-)-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1148) 4-Isopropyl-2-N--2-ylmethyl)-1H-imidazol-2-ylacetonitrile;

(1150) 4-Isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-2-freedomites-1H-imidazole;

(1151) Methyl 3-(4-isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)propionate;

(1152) 5-(3-Nitrophenylthio)-2-dimethylaminomethyl-4-isopropyl-1-methyl-1H-imidazole;

(1153) 5-(3-Chlorophenylthio)-4-isopropyl-2-N-methylcarbamoylmethyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1154) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-(3-phenylpropyl)-1H-imidazole;

(1155) 4-(3-Chlorophenylthio)-1-ethyl-5-isopropyl-1H-imidazol-2-ylmethanol;

(1156) 3-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-n-propyl-1H-imidazol-2-yl)propanol;

(1157) 3-(5-(3,5-Differenlty)-1-hexyl-4-isopropyl-1H-imidazol-2-yl)propanol;

(1158) 5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ilmatieteen;

(1159) 5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-2-freedomites-1H-imidazole;

(1160) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole-2-carbaldehyde the oxime;

(1161) 5-(3,5-Dichlorophenylthio)-4-isopropyl-2-N-methylthiocarbamate-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1162) 5-(3,5-Differenlty)-1-ethyl-4-isopropyl-1H-imidazol-2-ilmatieteen;

(1163) 2-(3-carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1-methyl-1H-imidazole;

(1164) 3-(5-(3,5-Differentiatio-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1166) 5-(3,5-Dimethylphenyl)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylmethanol;

(1167) 2-(2-Carbamoyloximes)methyl-5-(3,5-differenlty)-1-ethyl-4-isopropyl-1H-imidazole;

(1168) 2-Diaminomethylene-1-ethyl-4-isopropyl-5-phenylthio-1H-imidazole;

(1169) 2-(4-Isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(1170) 1-(2-(2-Carbamoylethyl)-5-(3,5-differenlty)- 4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(1171) 3-(4-Isopropyl-1-methyl-5-phenylthio-1H-imidazol-2-yl)propanol;

(1172) 2-Carbamoyloxymethyl-5-(3,5-dimethylphenyl)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1173) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1-h-imidazole-2-carbaldehyde the oxime;

(1174) N-(5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-4-ylmethyl)acetamide;

(1175) 2-(2-Acetoxyethyl)-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1176) 3-(5-(3,5-Differenlty)-1-vermeil-4-isopropyl-1H-imidazol-2-yl)propanol;

(1177) -(5-(3,5-Differenlty)-2-hydroxymethyl-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(1178) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1-h-imidazole;

(1179) 1-Ethyl-4-isopropyl-5-phenylthio-1H-imidazol-2-ylacetonitrile;

(1180) 5-(3,5-Dichloro is iridin-4-ylmethyl)-1H-imidazol-2-yl)ethanol;

(1182) 5-(3,5-Dichlorophenylthio)-2-diaminomethylene-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1183) 2-Aminomethyl-4-(3,5-differenlty)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1184) 1-n-Butyl-2-(3-carbamoylmethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazole;

(1185) 2-(4-Isopropyl-1-methyl-5-(3-forfinally)-1H-imidazol-2-yl)ethanol;

(1186) 1-Allyl-2-(2-carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(1187) 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(6-oxo-1,6-dihydropyridines-3-yl)methyl-1H-imidazol-2-yl)ethanol;

(1188) 5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-4-isopropyl-1-(quinoline-3-ylmethyl)-1H-imidazole;

(1189) 2-(1-(4-Aminobenzyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(1190) 5-(3,5-Dichlorophenylthio)-2-(3-carbamoyloximes)-1-vermeil-4-isopropyl-1H-imidazole;

(1191) 2-(4-Isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylethoxy)ethyl acetate;

(1192) 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylethoxy)ethyl acetate;

(1193) 2-Azidomethyl-1-ethyl-4-isopropyl-5-phenylthio-1H-imidazole;

(1194) 5-(3-Chlorophenylthio)-1-ethyl-4-isopropyl-2-N-methylcarbamoylmethyl-1H-imidazole;

(1195) 2-(1-(3-Aminobenzyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-2-yl)ethanol;
-1-ethyl-5-isopropyl-1H-imidazol-2-ilmatieteen;

(1198) 2-Dimethylaminomethyl-4-isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1199) 2-Aminomethyl-4-(3-nitrophenylthio)-1-ethyl-5-isopropyl-1H-imidazole;

(1200) -(5-(3,5-Dimethylphenyl)-2-hydroxymethyl - 4-isopropyl-1H-imidazol-2-yl)acetophenone;

(1201) 5-(3,5-Differenlty)-4-isopropyl-2-N-methyl(thiocarbamoyl)oxymethyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1202) 2-(2-Carbamoylethyl)-1-cyclopropylmethyl-5-(3,5 - differenlty)-4-isopropyl-1H-imidazole;

(1203) 2-Azidomethyl-4-isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1204) 2-(5-Isopropyl-4-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(1205) 5-(3,5-Dichlorophenylthio)-2-(3-carbamoyloximes)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazole;

(1206) 4-Isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylmethanol;

(1207) 3-(5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-yl)propanol;

(1208) 3-(1-(3-Aminobenzyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-2-yl)propanol;

(1209) 5-(3,5-Dichlorophenylthio)-2-dimethylaminomethyl-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1210) 4-Isopropyl-1-methyl-5-phenylthio-1H-imidazole-2-carbaldehyde the oxime;

(1211) 2-(5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylethoxy)et-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-yl)ethanol;

(1214) 5-Isopropyl-4-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ilmatieteen;

(1215) 2-(3-Carbamoyloximes)-4-isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1216) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylacetonitrile;

(1217) 4-Isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazole-2-carbaldehyde the oxime;

(1218) 1-Ethyl-4-isopropyl-2-N-methylcarbamoylmethyl-5-(3-forfinally)-1H-imidazole;

(1219) 5-Isopropyl-1-methyl-4-(3-forfinally)-1H-imidazole-2-carbaldehyde;

(1220) 5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-2-N-methylcarbamoylmethyl-1H-imidazole;

(1221) 3-(1-(3-Aminobenzyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)propanol;

(1222) 3-(5-(3,5-Differenlty)-1,4-aminobutiramida-1H-imidazol-2-yl)propanol;

(1223) 2-(2-Carbamoylethyl)-1-ethyl-4-isopropyl-5-phenylthio-1H-imidazole;

(1224) 3-(5-(3,5-Dichlorophenylthio)-1-hexyl-4-isopropyl-1H-imidazol-2-yl)propanol;

(1225) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ilmatieteen;

(1226) 4-(3-Nitrophenylthio)-5-isopropyl-1-methyl-1H-imidazol-2-ylmethanol;

(1227) 5-(3,5-Differenlty)-1-vermeil-4-isopropyl-1H-imidazol-2-ylmethanol;

(1228) 5-(3-Chlorophenylthio)-1-ethyl-4-isopropyl-2-N-methylaminomethyl-1H-imidazole;

(1229 isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylmethanol;

(1231) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylacetic;

(1232) 2-Carbamoyloxymethyl-5-isopropyl-1-methyl-4-(3-forfinally)-1H-imidazole;

(1233) 4-(3,5-Differenlty)-1-ethyl-5-isopropyl-1H-imidazole-2-carbaldehyde;

(1234) 5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole-2-carbaldehyde the oxime;

(1235) 2-(3-Carbamoylmethyl)-5-(3,5-dimethylphenyl)-1-ethyl-4-isopropyl-1H-imidazole;

(1236) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole-2-carbaldehyde;

(1237) 2-(2-amino-ethyl)-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1238) 5-(3-Nitrophenylthio)-1-ethyl-4-isopropyl-2-freedomites-1H-imidazole;

(1239) 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)ethanol;

(1240) 3-(4-Isopropyl-1-methyl-5-(3-forfinally)-1H-imidazol-2-yl)propanol;

(1241) Methyl 3-(5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-yl)propionate;

(1242) 2-(3-Carbamoyloximes)-4-isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1243) 4-(3,5-Differenlty)-5-isopropyl-1-methyl-1H-imidazol-2-ylmethanol;

(1244) 2-(4-Isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)ethanol;

(1245) 4-Isopropyl-1-methyl-5-phenylthio-1H-imidazol-2-ylmethanol;

(1246) 2-(2-�-vermeil-5-isopropyl-1H-imidazole;

(1248) 2-Aminomethyl-1-ethyl-5-isopropyl-4-(3-forfinally)-1H-imidazole;

(1249) 2-Carbamoyloxymethyl-4-isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1250) 2-(2-Acetoxyethyl)-1-ethyl-4-isopropyl-5-phenylthio-1H-imidazole;

(1251) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylacetic;

(1252) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-2-N-methylcarbamoylmethyl-1H-imidazole;

(1253) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazole;

(1254) 4-(3,5-Differenlty)-1-ethyl-5-isopropyl-1H-imidazol-2-ylmethanol;

(1255) 2-Carbamoyloxymethyl-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1256) 4-Isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazole-2-carbaldehyde;

(1257) 2-Azidomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1258) 2-(5-(3,5-Dimethylphenyl)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazol-2-yl)ethanol;

(1259) 2-(2-amino-ethyl)-5-(3-chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(1260) 2-(5-(3-Nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)ethanol;

(1261) 4-(3,5-Differenlty)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole-2-carbaldehyde;

(1262) 5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ilmeteo who yl)-5-(3,5-differenlty)-4-isopropyl-1-methyl-1H-imidazole;

(1265) 5-(3,5-Differenlty)-3-dimethylaminomethyl-4-isopropyl-1-methyl-1H-imidazole;

(1266) 5-(3,5-Dichlorophenylthio)-1-(2-carbamoylethyl)-2-(3-carbamoyloximes)-4-isopropyl-1H-imidazole;

(1267) 1,2-Di-(2-carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(1268) 2-Azidomethyl-4-(3,5-dichlorophenylthio)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1269) 2-Aminomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1270) 2-Acetamidomethyl-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1271) 2-Acetamidomethyl-4-isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1272) 2-Acetamidomethyl-4-isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1273) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1274) -(2-(2-Hydroxyethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(1275) -(5-(3,5-Dichlorophenylthio)-2-(3-carbamoyloximes)-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(1276) 5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ylmethanol;

(1277) N-(5-(3,5-Differenlty)-1-ethyl-4-isopropyl-1H-imidazole-4-ylmethyl)acetamide;

(1278) 1-Cyclopropylmethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-almeta is methyl-1-ethyl-4-isopropyl-5-phenylthio-1H-imidazole;

(1281) 5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-4-isopropyl-1-(3-phenylpropyl)-1H-imidazole;

(1282) 4-(3-Chlorophenylthio)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylmethanol;

(1283) 5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1284) 2-Acetamidomethyl-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1285) 3-(5-(3,5-Differenlty)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)propanol;

(1286) N-(5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-4-ylmethyl)acetamide;

(1287) 4-Isopropyl-2-N-methyl(thiocarbamoyl)oxymethyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1288) Methyl 3-(5-(3-chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)propionate;

(1289) 2-(1-Ethyl-5-isopropyl-4-(3-forfinally)-1H-imidazol-2-ylethoxy)ethanol;

(1290) 1-Benzyl-2-carbamoyloxymethyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazole;

(1291) 5-(3-Nitrophenylthio)-4-isopropyl-1-methyl-2-freedomites-1H-imidazole;

(1292) 2-(2-Carbamoyloximes)methyl-4-isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1293) 2-(2-Carbamoylethyl)-4-isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1294) 2-(2-Azidoethyl)-5-(3-nitrophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(1295) 2-(2-One-2-ylmethyl)-1H-imidazole;

(1297) 5-(3,5-Differenlty)-4-isopropyl-2-methanesulfonamido-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1298) 1-(2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(1299) 3-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(2-methylpyridin-3-ylmethyl)-1H-imidazol-2-yl)propanol;

(1300) 2-Aminomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1301) 2-Aminomethyl-4-isopropyl-1-methyl-5-phenylthio-1H-imidazole;

(1302) 2-(1-Ethyl-4-isopropyl-5-phenylthio-1H-imidazol-2-ylethoxy)ethanol;

(1303) 2-(4-(3,5-Differenlty)-1-ethyl-5-isopropyl-1H-imidazol-2-ylethoxy)ethanol;

(1304) 2-(2-Carbamoylethyl)-1,4-aminobutiramida-5-(3,5-dimethylphenyl)-1H-imidazole;

(1305) 2-(1-Benzyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(1306) 5-(3,5-Differenlty)-4-isopropyl-2 - methanesulfonamido-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1307) Methyl 3-(4-isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)propionate;

(1308) 2-(1-Ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazol-2-ylethoxy)ethanol;

(1309) Methyl 3-(5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-yl)propionate;

(1310) 2-(5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)ethanol;

(1311) 2-(2-Acetoxyethyl)-ethoxy)methyl-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1313) 2-Aminomethyl-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1314) 1-Ethyl-5-isopropyl-4-phenylthio-1H-imidazole-2-carbaldehyde;

(1315) 2-(5-(3,5-Differenlty)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanol;

(1316) 3-(1-Allyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)propanol;

(1317) 2-(4-Isopropyl-1-methyl-5-(3-forfinally)-1H-imidazol-2-ylethoxy)ethyl acetate;

(1318) 5-(3,5-Dichlorophenylthio)-1,4-aminobutiramida-1H-imidazol-2-ylmethanol;

(1319) 2-Azidomethyl-4-(3-nitrophenylthio)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1320) 5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylacetic;

(1321) 5-(3,5-Dichlorophenylthio)-2-diaminomethylene-4-isopropyl-1-methyl-1H-imidazole;

(1322) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1-(3-(pyridin-4-yl)propyl)-1H-imidazole;

(1323) 5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylmethanol;

(1324) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-1-vermeil-4-isopropyl-1H-imidazole;

(1325) 5-(3,5-Differenlty)-1,4-aminobutiramida-1H-imidazol-2-ylmethanol;

(1326) 3-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(quinoline-3-ylmethyl)-1H-imidazol-2-yl)propanol;

(1327) 4-Isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazole-2-carbaldehyde hydrail-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1330) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ilmatieteen;

(1331) 2-(5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(1332) 2-(4-(3-Chlorophenylthio)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(1333) 5-(3-Nitrophenylthio)-4-isopropyl-2-N-methylaminomethyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1334) N-(5-(3-Chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole-4-ylmethyl)acetamide;

(1335) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-4-ilmatieteen;

(1336) 3-(5-(3-Nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)propanol;

(1337) 3-(1-n-Butyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)propanol;

(1338) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-1-vermeil-4-isopropyl-1H-imidazole;

(1339) 5-(3,5-Dichlorophenylthio)-4-isopropyl-2-N-methyl(thiocarbamoyl)oxymethyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1340) 2-(2-Acetoxyethyl)-4-isopropyl-1-methyl-5-(3-forfinally)-1H-imidazole;

(1341) 5-(3,5-Differenlty)-1-ethyl-4-isopropyl-2-N-methylthiocarbamate-1H-imidazole;

(1342) 2-(3-Carbamoylmethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1-methyl-1H-imidazole;

(1343) 2-(2-Carbamoyloximes)methyl-4-isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole;<4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole-2-carbaldehyde hydrazone;

(1346) N-(5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-4-ylmethyl)acetamide;

(1347) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1348) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-2-N-methylaminomethyl-1H-imidazole;

(1349) 2-Carbamoyloxymethyl-4-isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1350) 5-(3-Nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2 - ilmatieteen;

(1351) 5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole-2-carbaldehyde;

(1352) 2-(4-Isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(1353) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1354) 5-(3,5-Dichlorophenylthio)-2-(2-carbamoylethyl)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1355) 4-(3-Nitrophenylthio)-1-ethyl-5-isopropyl-1H-imidazole-2-carbaldehyde;

(1356) 2-(4-Isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylethoxy)ethyl acetate;

(1357) 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylethoxy)ethanol;

(1358) 5-(3-Nitrophenylthio)-4-isopropyl-2-methanesulfonamido-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1359) 5-(3,5-Differenlty)-4-isopropyl-2-N-methylcarbamoyl ethyl-1H-imidazole;

(1361) 3-(1-Benzyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazol-2-yl)propanol;

(1362) 2-(4-(3,5-Differenlty)-5-isopropyl-1-methyl-1H-imidazol-2-ylethoxy)ethanol;

(1363) 5-(3-Chlorophenylthio)-4-isopropyl-2-methanesulfonamido-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1364) 2-(2-Azidoethyl)-1-ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazole;

(1365) 3-(1-Benzyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)propanol;

(1366) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole-2-carbaldehyde;

(1367) 5-(3,5-Differenlty)-4-isopropyl-1-n-propyl-1H-imidazol-2-ylmethanol;

(1368) 4-Isopropyl-2-N-methylcarbamoylmethyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1369) 2-Acetamidomethyl-1-ethyl-4-isopropyl-5-phenylthio-1H-imidazole;

(1370) 2-Carbamoyloxymethyl-1-ethyl-4-isopropyl-5-phenylthio-1H-imidazole;

(1371) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ylacetic;

(1372) 1-(2-Carbamoyloxymethyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(1373) 2-(4-Isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylethoxy)ethyl acetate;

(1374) 2-(5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)ethanol;

(1375) 3-(1-n-Butyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazol-2-yl)propanol;

(1378) 2-(3-Carbamoylmethyl)-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1379) 5-(3-Chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ilmatieteen;

(1380) 2-Azidomethyl-4-isopropyl-1-methyl-5-(3-forfinally)-1H-imidazole;

(1381) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazole;

(1382) 2-Azidomethyl-5-(3-chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(1383) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(2-(pyridin-4-yl)-ethyl)-1H-imidazol-2-ylmethanol;

(1384) 5-(3,5-Dichlorophenylthio)-4-isopropyl-2-N-methylaminomethyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1385) 5-(3,5-Dichlorophenylthio)-2-(3-carbamoyloximes)-4-isopropyl-1-(quinoline-3-ylmethyl)-1H-imidazole;

(1386) 2-(5-(3,5-Differenlty)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazol-2-yl)ethanol;

(1387) 2-Carbamoyloxymethyl-4-(3-chlorophenylthio)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1388) 5-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-1-cyclopropylmethyl-4-isopropyl-1H-imidazole;

(1389) 2-Carbamoyloxymethyl-5-(3,5-differenlty)-1-vermeil-4-isopropyl-1H-imidazole;

(1390) 2-(2-Azidoethyl)-4-isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1391) 5-(3-Nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazole-2-carbaldehyde hydrazone;

(1392) who yl)-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1394) 2-(2-Carbamoyloximes)methyl-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1395) 2-(3-Carbamoyloximes)-1,4-aminobutiramida-5-(3,5-dimethylphenyl)-1H-imidazole;

(1396) 1-Ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazol-2-ylmethanol;

(1397) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1-(2-(pyridin-4-yl)ethyl)-1H-imidazole;

(1398) 5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ilmatieteen;

(1399) 1-Ethyl-5-isopropyl-4-(3-forfinally)-1H-imidazol-2-ilmatieteen;

(1400) 2-(5-(3,5-Dimethylphenyl)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)ethanol;

(1401) 1-Ethyl-4-isopropyl-2-methanesulfonamido-5-phenylthio-1H-imidazole;

(1402) 2-Aminomethyl-4-(3,5-dichlorophenylthio)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1403) 2-(2-Azidoethyl)-4-isopropyl-1-methyl-5-(3-forfinally)-1H-imidazole;

(1404) 2-Diaminomethylene-1-ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazole;

(1405) 2-Azidomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1406) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-2-N-methyl-(thiocarbamoyl)oxymethyl-1H-imidazole;

(1407) 2-(3-Carbamoylmethyl)-5-(3,5-Differenlty)-4-isopropyl-1-(2-phenylethyl)-1H-imidazole;

(1408) 5-(3-Chlorophenylthio)-2-diisopropyl-1H-imidazole;

(1410) 2-(2-Azidoethyl)-5-(3,5-differenlty)-4-isopropyl-1-methyl-1H-imidazole;

(1411) 2-(2-Carbamoyloximes)methyl-5-(3-chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(1412) 2-Azidomethyl-4-(3,5-dichlorophenylthio)-5-isopropyl-1-methyl-1H-imidazole;

(1413) 3-(5-(3,5-Differenlty)-4-isopropyl-1-methyl-1H-imidazol-2-yl)propanol;

(1414) 2-2-(Acetoxyethyl)-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1415) 2-(1-Benzyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(1416) 2-Azidomethyl-4-(3-chlorophenylthio)-5-isopropyl-1-methyl-1H-imidazole;

(1417) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylacetonitrile;

(1418) 2-(2-Acetoxyethyl)-4-isopropyl-5-phenylthio-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1419) 5-(3,5-Differenlty)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole-2-carbaldehyde hydrazone;

(1420) 4-Isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylacetic;

(1421) 2-Diaminomethylene-4-isopropyl-5-(3-forfinally)-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1422) 2-Acetamidomethyl-1-ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazole;

(1423) 1-Ethyl-4-isopropyl-5-phenylthio-2-freedomites-1H-imidazole;

(1424) 2-Carbamoyloxymethyl-1,4-aminobutiramida-5-(3,5-dimethylphenyl)-1H-imidazole;

(1425) 3-(5-(3,5-D-1H-imidazole-2-carbaldehyde the oxime;

(1427) 5-(3,5-Dimethylphenyl)-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ylmethanol;

(1428) 3-(1-Cyclopropylmethyl-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazol-2-yl)propanol;

(1429) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-n-propyl-1H-imidazol-2-ylmethanol;

(1430) 1-(3-Aminobenzyl)-5-(3,5-dichlorophenylthio)-2-(3-carbamoyloximes)-4-isopropyl-1H-imidazole;

(1431) 5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde the oxime;

(1432) 5-(3-Chlorophenylthio)-4-isopropyl-2-N-methyl(thiocarbamoyl)-oxymethyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1433) 1-(2-(3-Carbamoylmethyl)-5-(3,5-dimethylphenyl)-4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(1434) 2-(3-Carbamoyloximes)-4-isopropyl-1-methyl-5-(3-forfinally)-1H-imidazole;

(1435) 5-(3,5-Differenlty)-4-isopropyl-1-methyl-2-N-methylaminomethyl-1H-imidazole;

(1436) 4-(3,5-Dichlorophenylthio)-1-ethyl-5-isopropyl-1H-imidazol-2-ylmethanol;

(1437) alpha-(5-(3,5-Differenlty)-2-hydroxymethyl-4-isopropyl-1H-imidazol-1-yl)acetophenone;

(1438) Methyl 3-(5-(3-nitrophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl)propionate;

(1439) 2-Azidomethyl-1-ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazole;

(1440) 2-(2-Carbamoylethyl)-5-(3-chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(1441) 3-(5-(3,5-Dichlorophenylthio)-1-n-bout who-1H-imidazole;

(1443) 3-(5-(3,5-Dichlorophenylthio)-1-cyclopropylmethyl-4-isopropyl-1H-imidazol-2-yl)propanol;

(1444) 2-(2-Acetoxyethyl)-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1445) 4-Isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazol-2-ilmatieteen;

(1446) 4-(3,5-Dichlorophenylthio)-5-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde;

(1447) 5-(3-Chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-ylmethanol;

(1448) 5-(3-Chlorophenylthio)-2-dimethylaminomethyl-4-isopropyl-1-methyl-1H-imidazole;

(1449) 2-(4-Isopropyl-1-methyl-5-phenylthio-1H-imidazol-2-ylethoxy)ethanol;

(1450) 3-(5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-yl)propanol;

(1451) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole-2-carbaldehyde;

(1452) 1-Ethyl-4-isopropyl-5-phenylthio-1H-imidazol-2-ylmethanol;

(1453) 2-(2-Carbamoyloximes)methyl-5-(3-nitrophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(1454) 2-Azidomethyl-1-ethyl-5-isopropyl-4-(3-forfinally)-1H-imidazole;

(1455) 3-(5-(3,5-Dimethylphenyl)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-yl)propanol;

(1456) 2-(5-(3,5-Differenlty)-1-ethyl-4-isopropyl-1H-imidazol-2-ylethoxy)ethanol;

(1457) 2-(2-amino-ethyl)-5-(3-nitrophenylthio)-4-isopropyl-1-methyl-1H-imidazole;

(1458) 2-(3-Carbamoyloximes)-5 is Tyl-4-isopropyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1460) 1-Ethyl-4-isopropyl-2-N-methylaminomethyl-5-phenylthio-1H-imidazole;

(1461) 5-(3-Chlorophenylthio)-4-isopropyl-2-N-methylcarbamoylmethyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1462) 5-(3,5-Differenlty)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde;

(1463) 2-Diaminomethylene-5-(3,5-differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1464) 2-Azidomethyl-4-isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1465) 2-(1-n-Butyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)ethanol;

(1466) 2-(2-Carbamoylethyl)-5-(3-nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1467) 3-(4-Isopropyl-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazol-2-yl)propanol;

(1468) 2-(3-Carbamoylmethyl)-5-(3,5-differenlty)-1-vermeil-4-isopropyl-1H-imidazole;

(1469) 5-(3-Nitrophenylthio)-4-isopropyl-2-N-methylcarbamoylmethyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1470) 2-Carbamoyloxymethyl-4-(3-nitrophenylthio)-5-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1471) 5-(3-Chlorophenylthio)-4-isopropyl-2-N-methylcarbamoylmethyl-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1472) 4-(3-Nitrophenylthio)-1-ethyl-5-isopropyl-1H-imidazol-2-ylmethanol;

(1473) 2-(2-Azidoethyl)-5-(3-chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1474 ropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-yl)propionate;

(1476) 5-Isopropyl-4-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ilmatieteen;

(1477) 2-(2-Azidoethyl)-5-(3,5-dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(1478) 1-n-Butyl-2-(3-carbamoylmethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(1479) 3-(1-n-Butyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-yl)propanol;

(1480) 4-Isopropyl-1-methyl-5-phenylthio-2-freedomites-1H-imidazole;

(1481) 5-(3,5-Differenlty)-2-dimethylaminomethyl-1-ethyl-4-isopropyl-1H-imidazole;

(1482) 1-(2-(2-Hydroxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-1-yl)-2-propanone;

(1483) 2-(2-Carbamoylethyl)-5-(3,5-differenlty)-1-ethyl-4-isopropyl-1H-imidazole;

(1484) 5-(3-Nitrophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylmethanol;

(1485) 5-(3,5-Dichlorophenylthio)-4-isopropyl-2-methanesulfonamido-1-methyl-1H-imidazole;

(1486) 2-(5-(3,5-Differenlty)-4-isopropyl-1-(2-phenylethyl)-1H-imidazol-2-yl)ethanol;

(1487) 1-(4-Aminobenzyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazol-2-ylmethanol;

(1488) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazole-2-carbaldehyde the oxime;

(1489) 2-Carbamoyloxymethyl-5-(3,5-dimethylphenyl)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazole;

(1490) 3-(4-Isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-immortality)-1-(2-carbamoylethyl)-4-isopropyl-1H-imidazol-2-ylmethanol;

(1493) 5-(3,5-Dichlorophenylthio)-1-hexyl-4-isopropyl-1H-imidazol-2-ylmethanol;

(1494)5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylacetic;

(1495) 4-(3,5-Dichlorophenylthio)-2-carbamoyloxymethyl-5-isopropyl-1-methyl-1H-imidazole;

(1496) 1,4-Aminobutiramida-5-(3,5-differenlty)-1H-imidazol-2-ylmethanol;

(1497) 2-(5-(3-Chlorophenylthio)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylethoxy)ethyl acetate;

(1498) N-(4-Isopropyl-5-(3-forfinally)-1-(pyridine-4-ylmethyl)-1H-imidazol-4-ylmethyl)acetamide;

(1499) 2-Azidomethyl-5-isopropyl-4-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazole;

(1500) 2-(2-Carbamoyloximes)methyl-1-ethyl-4-isopropyl-5-(3-forfinally)-1H-imidazole;

(1501) 3-(5-(3,5-Dichlorophenylthio)-1-(2-carbamoylethyl)-4-isopropyl-1H-imidazol-2-yl)propanol;

(1502) 4-Isopropyl-2-methanesulfonamido-5-phenylthio-1-(pyridine-2-ylmethyl)-1H-imidazole;

(1503) 1-Benzyl-2-(2-carbamoylethyl)-5-(3,5-differenlty)-4-isopropyl-1H-imidazole;

(1504) Methyl 3-(5-(3,5-differenlty)-4-isopropyl-1-(pyridine-3-ylmethyl)-1H-imidazol-2-yl)propionate;

(1505) 5-(3-Chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-ilmatieteen;

(1506) 4-Isopropyl-5-phenylthio-1-(pyridine-4-ylmethyl)-1H-imidazol-2-ylmethanol;

(1507) 1-(5-(3,5-Differenlty)-2-hydroxymethyl-4-isop Gasol;

(1509) 4-Isopropyl-5-(3-forfinally)-1-(pyridine-3-ylmethyl)-1H-imidazol-2-ylmethanol; and

(1510) 2-(2-Azidoethyl)-4-isopropyl-1-methyl-5-phenylthio-1H-imidazole.

In accordance with the present invention can be used any salts of the above compounds, provided that they are pharmaceutically acceptable. As example can be mentioned salts formed with mineral acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, hydrofluoric acid, Hydrobromic acid, etc; salts formed with organic acids such as formic acid, acetic acid, tartaric acid, lactic acid, citric acid, fumaric acid, maleic acid, succinic acid, methanesulfonate acid, econsultancy acid, benzolsulfonat acid, toluensulfonate acid, naphthalenesulfonate acid, camphorsulfonic acid and so forth; and salts formed alkali or alkaline earth metals, such as sodium, potassium, calcium, etc.

Compounds of the present invention are new compounds, obtained by the authors of this application, and as will be shown below, they represent the Yu transcriptase of HIV-1 (NNRT1).

Activity videocasting compounds comparable to the activity of AZT (azidothymidine), and in the analytical system using peripheral blood lymphocytes of infected person fresh insulator virus, these compounds find higher activity than AZT. In addition, these compounds possess strong activity against AZT-resistant virus strains and mutants that detect cross-resistance to many NNRT1, and the emergence of resistant strains in vitro in this case is slower than in the case of nevirapine, where the locus of mutation is also different.

In addition, the above compounds with a high degree of effectiveness transferred to the lymph nodes, and their concentration in the lymph nodes is maintained at a level much greater than the 90% inhibitory concentration in vitro. In addition, the above compounds are highly safe drug and have very low toxicity.

Thus, the compounds of the present invention can be successfully used as a drug against HIV, and, taken together with AZT, they have a synergistic dei is mikeski synthesized by standard methods using known compounds. General methods of preparing compounds of the present invention are described in more detail below.

Typical compounds of the present invention can be synthesized by condensation of imidazoles with thiophenols in accordance with the following reaction scheme (scheme, see the end of the description).

In addition, using as starting compounds, the compounds represented by the General formula or , it is possible to synthesize compounds of the present invention having various 2-substituted groups, by modifying the 2-side chain imidazole ring.

In this method of synthesis of any Deputy is reactive and the reaction can be carried out with prior protection Deputy suitable protective group.

B of reaction scheme I, R1, R3X and Y are the same as defined above, a is a halogen, R2'represents the type of R2that can be used in this reaction, or hydrogen. P represents hydrogen or a group of the formula

< / BR>
(Stage 1)

In this stage, the halogen (e.g. chlorine, bromine or iodine) injected into the imidazole derivative in the presence of a base. At the same time, especially predpochtitelnye (for example, sodium hydroxide or potassium hydroxide) in a solvent such as methylene chloride or telengard. The connection can be synthesized by the method described in EP-585014.

(Phase 2)

In this stage, the compound is subjected to condensation with thiophenolate derived compounds That thiophenolate derived (thiophenol or a corresponding disulfide) is dissolved in a suitable solvent (for example, N,N-dimethylformamide, tetrahydrofuran, dimethyl sulfoxide) and to this solution, in the presence of a strong base (such as lithium hydride, sodium hydride or potassium hydride) add imidazolidin obtained in the previous stage. In this stage get phenylthiazol formula or tautomer.

(Stage 3)

At this stage, R1injected into the N-position of the imidazole ring. Thus, in the N-position enter Deputy. For example, a halide of the desired substituent (i.e., R1A) is subjected to reaction with phenylthiomethyl or tautomers obtained in the previous stage. This reaction is carried out in the presence of a strong base (such as lithium hydride or sodium hydride) in an aprotic solvent such as N,N-dimethylformamide or dimethylsulfoxide. At this stage, get with the quality of the original connection and choosing substitutes for 2-position of the imidazole ring, you can get another type of compounds of the present invention. Methods (A) - (D) synthesis of these compounds is described below with reference to the corresponding reaction schemes.

In reaction scheme II, R1, R3X and Y are the same as defined above. Rarepresents hydroxy or a substituted or an unsubstituted amino group).

(Stage 1)

In this stage, the formyl group is introduced in the 2-position of the imidazole part. This stage is carried out using the reaction of the compounds with N,N-dimethylformamide in the presence of a strong base, for example, utility, and in a solvent such as tetrahydrofuran.

(Phase 2)

In this stage, the formyl group in the 2-position of the imidazole part of the turn in hydroxymethylene group. This stage is carried out by reconnection with the use of reducing agents, such as borohydride sodium, and in a solvent such as ethanol or methanol.

(Stage 3)

In this stage, the formyl group in the 2-position of the imidazole part of the turn in oxymora or hydrazone group. This compound is subjected to reaction with hydroxylamine hydrochloride or hydrazine hydrate in a solvent such as methanol or etano is represents hydrogen, acyl or substituted or unsubstituted carbarnoyl or thiocarbamoyl, R2brepresents alkyl.

(Stage 1)

In this stage 2-hydroxymethylene group of the imidazole part of the connection is subjected to acylation. This stage can be carried out using the reaction of compound c allermuir agent (e.g. acid chloride such as acetylchloride or propionitrile, or with an acid anhydride such as acetic anhydride) in the presence of a base such as triethylamine) in a solvent such as methylene chloride or telengard.

(Phase 2)

In this stage 2-hydroxymethylene group imidazole connection parts are carbamoylethyl. This stage can be carried out using the reaction of compounds with carbamoylethyl agent (for example, trichlorotriazine or chlorosulfonylisocyanate) in a solvent such as tetrahydrofuran or glyme.

(Stage 3)

In this stage, the acyl part of acylamino-group compounds were subjected to hydrolytic elimination and received carbamoyl connection This stage can be carried out by heating the compound in the presence of organic bases (for example, theta and subsequent stage acetaldehyde group to give 2-hydroxy-group of the imidazole part of the First connection connection 9 is subjected to reaction with 2-bromo-1,3-dioxolane in the presence of a strong base, such as sodium hydride or potassium hydride in a solvent such as N,N-dimethylformamide, tetrahydrofuran or dimethylsulfoxide.

(Stage 5)

Aldehyde protective group at the 2-side chain imidazole ring compounds 14, obtained in the previous stage, helps eliminate by acid hydrolysis. This stage can be carried out by treating the compound with a mineral acid, such as hydrochloric acid in methanol.

(Stage 6)

In this stage, the aldehyde group in the compound obtained in the previous stage, reduced to the corresponding alcohol (R2a= H), and then, if necessary, impose Deputy, such as acyl, carnemolla or thiocarbamoyl group. So, for example, the connection restore using a reducing agent such as sodium borohydride in a solvent such as ethanol or methanol, resulting in a gain alcohol (R2a= N). When the acylation, carbamoylation or thiocarbamoylation alcohol, using well-known techniques obtain the corresponding acyl derivative (R2a= acyl), carbamoyl derivative (R2a= carbarnoyl) or thiocarbamoyl derivative (R2a= thiocarbamoyl). Konkretnyie, as they were defined above. R2cand R2dindependently represent hydrogen or alkyl.

(Stage 1)

In this stage, the halogen is introduced into hydroxymethylene group in 2-position of the imidazole part. This stage is carried out using the reaction of compounds with gloriouse agent such as thionyl chloride, phosphorus oxychloride or trichloride phosphorus, in a solvent such as N,N-dimethylformamide, tetrahydrofuran or dimethylsulfoxide.

(Phase 2)

In this stage, the halide obtained in the previous stage, transformed into azide. This stage is carried out using the reaction of compounds with azide such as sodium azide or potassium azide, in a solvent such as N,N-dimethylformamide or dimethylsulfoxide.

(Stage 3)

In this stage, the azide compound obtained in the previous stage, reduced to the amino compound. For example, the compound is subjected to reaction with triphenylphosphine in a solvent such as tetrahydrofuran, N,N-dimethylformamide or dimethylsulfoxide.

In reaction scheme V R1, R2c, R3X and Y are the same as defined above.

(Stage 1)

In this stage halogenmethyl group in 2-position of the imidazole hour the shares connections with tianyoude agent, such as potassium cyanide or sodium cyanide, in a solvent such as N,N-dimethylformamide, tetrahydrofuran or dimethylsulfoxide.

(Phase 2)

In this stage, the cyano compound obtained in the previous stage, is subjected to the carboxylation or esterification. For example, the connection process gas (dry) chlorocarbon in a solvent such as methanol or ethanol, and neutralize, for example, sodium bicarbonate or potassium carbonate, resulting in a gain of methyl or ethyl ester (R2c= methyl or ethyl). This ester is subjected to conventional alkaline hydrolysis, resulting receive free carboxylic acid (R2c= N).

In reaction scheme VI, R1, R2', R3X, Y and Z are as defined above.

Compounds in which Z is SO or SO2can be obtained by reaction of the sulfide compound with one or more equimolar amount of an oxidant, such as periodate sodium m-chlorbenzene acid, aqueous solution of hydrogen peroxide, sodium dichromate, potassium permanganate, chromic acid or selenium dioxide, in a solvent such as methylene chloride or acetonitrile, and then, aluminia.

In addition, in the same manner as that described in the Main method of synthesis (1), by modification of the 2-side chain imidazole ring can be obtained from the class of compounds of the present invention having different substituents in the 2-position.

B of reaction scheme VII, R1, R2, R3X and Y are the same as defined above.

(Stage 1)

In the main method of synthesis (3) as the source of the connections are right-acylamino--substituted ketone compound This compound is subjected to cyclodehydration by heating with ammonia or its salt formed by an organic or inorganic acid, in an organic solvent, for example acetic acid, at room temperature or under conditions of heating under reflux, resulting in the formation of the imidazole ring.

(Phase 2)

This stage is carried out in the same way that was described in Stage 3 Primary method of synthesis (1).

By modification of the 2-side chain imidazole ring in the same manner as that described in the Main method of synthesis (1) may be obtained from the class of compounds of the present invention having different substituents in the 2-La oral administration of the compounds of the present invention can be used in any of the standard pharmaceutical form, for example, in the form of solid dosage forms such as tablets, powders, granules, capsules, etc. ; solutions, oil suspensions; and liquid dosage forms such as syrups and elixirs. For parenteral administration the compounds of the present invention can be used in the form of an injectable aqueous or oil suspensions. In the manufacture of such dosage forms can be selectively used standard fillers, binders, sizing, aqueous solvents, oily solvents, emulsifiers, suspendresume agents, etc. in Addition, the pharmaceutical compositions may also have other additives such as preservatives and stabilizers. The dose of a compound of the present invention or its salts depends on the method of administration, age, body weight and clinical condition of the patient, and the type of the disease. However, in General, the daily dose for oral administration of the compounds of the present invention is from 0.05 to 3000 mg, and preferably from 0.1 to 1000 mg, and the daily dose for parenteral administration is from 0.1 to 1000 mg, and preferably from 0.05 to 500 mg, and this dose can be introduced in the form of 1-5 divided doses.

Now izaberete is that, however, should not be construed as a limitation of the scope of the invention.

Example 1

Synthesis of 5-(3,5-dichlorophenylthio)-1,2-dimethyl-4-isopropyl-1H - imidazole (Compound 1-1)

4-Isopropyl-2-Mei (3a) was synthesized by the method described in EP-A-585014, and 5-iodine-4-isopropyl-2-Mei (4a) and 5-(3,5-dichlorophenylthio)-4-isopropyl-2-methyl-1H-imidazole (5a) was synthesized by the method described in Japanese patent application Koka Hei 5-255270.

In anhydrous N, N-dimethylformamide (8 ml) was dissolved 400 mg (1.3 mmol) of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-methyl-1H-imidazole (5a), and then, with ice cooling, was added 80 mg (2.0 mmol) of sodium hydride. After keeping for 5 minutes, to the mixture was added 245 mg (1,73 mm) under the conditions. After 30 minutes the reaction mixture was poured into ice water and was extracted with diethyl ether. The extract was washed with water, dried with sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by chromatography on silica gel (ethyl acetate:n-hexane 1:2) and then recrystallized from n-hexane, resulting in received 313 mg (75% yield) of 5-(3,5 - dichlorophenylthio)-1,2-dimethyl-4-isopropyl-1H-imidazole (Compound 1-1). So pl.: 95-96oC.

1H-NMR (CDCl3- H16Cl2N2S):

Calculated: C 53,34 H 5,12 Cl 22,49 N 8,89 (%)

Found: C 53,05 To 5.21 H Cl 22,40 N 8,96 (%).

Example 2

Synthesis of 5-(3,5-dimethylphenyl)-1,2-dimethyl-4-isopropyl-1H - imidazole (Compound 1-2)

Compound 1-2 was obtained by the synthesis method described in example 1 for Compounds 1-1.

1H-NMR (CDCl3- TMS) million D.: a 1.25 (d, J=7,0 Hz. 6H), 2,22 (s, 6H), to 2.46 (s, 3H), and 3.16 (Sep., 1H), 3,42 (s, 3H), return of 6.58 (s, 2H), 6.75 in (s, 1H).

Example 3

Synthesis of 5-(3-chlorophenylthio)-1,2-dimethyl-4-isopropylimidazole (Compound 1-3)

Compound 1-3 was obtained from 5-(3-chlorophenylthio)-4-isopropyl-2 - methylimidazole by the method of synthesis described in example 1 for Compounds 1-1 (yield 47%).

So pl.: 91-94oC.

1H-NMR (CDCl3- TMS) million D.: a 1.25 (d,J=7.2 Hz, 6H), to 2.46 (s, 3H), is 3.08-3,2 (m, 1H), 3,42 (s, 3H), 6,80 ~at 6.84 (m, 1H), 6,94 (t, J= 2.4 Hz, 1H), 7,1 ~7,2 (m, 1H)

Example 4

Synthesis of 1-benzyl-5-(3,5-dimethylphenyl)-4-isopropyl-2 - methylimidazole (Compound 1-4)

Compound 1-4 was obtained by the synthesis method described in example 1 for Compounds 1-1.

So pl.: 94-97oC.

1H-NMR (CDCl3- TMS) million D.: of 1.28 (d,J=6.6 Hz, 6H), of 2.45 (s, 3H), 3,05-3,2 (m, 1H), is 5.06 (s, 2H), of 6.68 (d,J=1.8 Hz, 2H), 6,9 (DD,J=0,9, 1.8 Hz, 2H), 6,99 (t,J=1.8 Hz, 1H), 7,1-7,3 (m, 4H).

Elemental analysis for C20H20< Example 5

Synthesis of 1,2-dimethyl-5-(3,5-dimethylphenyl)-4-ethylimidazole (Compound 1-5)

In anhydrous dimethylformamide (4 ml) was dissolved 200 mg (0.8 millimoles) of 5-(3,5-dimethylphenyl)-4-ethyl-2-methylimidazole (5), and then was added 49 mg (1.2 millimoles) of 60% sodium hydride, cooling the thus ice, and the resulting mixture was stirred for five minutes, To this mixture was added 138 mg (1.00 mmol) under the conditions, and then was stirred for 30 minutes. The reaction mixture was poured into ice water and was extracted with diethyl ether. The organic layer was dried with sodium sulfate. After that, the solvent was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (eluent:ethyl acetate/methylene chloride = 1 : 1). From the first fraction was obtained 40 mg (yield 19%) of isomer position (b') of the target compound as an oily substance. From the latter fraction was obtained 140 mg of 1,2-dimethyl-5-(3,5-dimethylphenyl)-4-ethylimidazole (Compound 1-5) in the form of oily substance (yield 66%).

(b'):1H-NMR (CDCl3-TMS) million D.: 1,09 (t, J = 7.4 Hz, 3H), of 2.21 (s, 6N), is 2.40 (s, 3H), 2,70 (kV, J = 7,4 Hz, 2H), 3,51 (s, 3H), 6,70 (m, 1H), 6,77 (m, 2H).

Compound 1-5 (oily substance):1H-NMR (CDCl3-TMS) million D.: 1,22 (t, J = 7,6 Hz, 3H), 2,22 thio)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde (Compound 1-6)

In 350 ml of acetonitrile was dissolved 70 g (0,452 mol) of 2,2-dichloro-3-methylbutyraldehyde (1), and then added 74 g (0,913 mol) of 37% formalin. To the resulting mixture under ice cooling was added 616 ml of 28% aqueous ammonia solution, and then the mixture was stirred at room temperature for 66 hours. The resulting reaction mixture was concentrated under reduced pressure and the resulting residue was extracted with methylene chloride. The extract was dried with sodium sulfate, filtered and concentrated under reduced pressure, resulting in the received mixture of 4-isopropylimidazole (3b) and (4-isopropyl-1H-imidazol-2-yl)Isopropylamine (3b') as a yellow oily substance. 39.5 g of the above oily substance was dissolved in 199 ml of methylene chloride, and the resulting solution was added a solution of sodium hydroxide (28,7 g) in water (287 ml). Thereafter, while cooling with ice and with stirring drop by drop) was added a solution containing iodine (182 g, 0,716 mol) and methylene chloride (910 ml) in methanol (455 ml). After complete addition, the mixture was stirred under ice cooling for 30 minutes. To the obtained solution was added an aqueous solution of sodium thiosulfate, and the mixture was neutralized by adding hydrochloric acid and then was extracted was methylcholantrene under reduced pressure. The residue was recrystallized from diisopropyl ether, resulting in received of 55.9 g (yield 43%) of 2,5-diiodide-4 - isopropyl-1H-imidazole (7).

The filtrate obtained by filtration of 2.5-diid - 4-isopropyl-1H-imidazole (7), concentrated under reduced pressure and then the residue was subjected to chromatography on silica gel, elwira first 1% methanol/methylene chloride, then 5% methanol/methylene chloride. The eluate was recrystallized from ethyl acetate/isopropyl ether, resulting in the received 7.6 g (yield 6%) (5-iodine-4-isopropyl-1H-imidazol-2-yl)Isopropylamine (8). Melting point: 138-140oC.1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J = 7,0 Hz, 6H), of 1.35 (d, J = 7,0 Hz, 6H), 3,14 (Sept., 1H), 3,88 (Sept., 1H), 11,35 (fat.. 1H).

IR (film) cm-1: 3232, 1655.

Elemental analysis of C10H15N2IO):

Calculated (%): C 39,23 H 4,94 N 9,15 I is 41.45

Found: (%): C 39,15 H 4,95 N 9,12 I 41,43.

In 240 ml of ethanol was dissolved of 48.1 g (0.144 mol) of 2,5-diid-4 - isopropyl-1H-imidazole (7), and then added 240 ml of water and 20.1 g (strength of 0.159 mol) of sodium sulfate. The resulting mixture was heated at a temperature of 85oC for 35 minutes. This reaction mixture was concentrated and extracted with methylene chloride, and then the extract was washed water is the action scene the residue was washed with ethyl acetate/diisopropyl ether and filtered, as a result, we got to 26.9 g (yield 86%) of 4-isopropyl-5-iodine-1H-imidazole (4b).

1H-NMR (CDCl3- TMS) million D.: 1,32 (d, J = 7.2 Hz, 6H), is 3.08 (Sept., 1H), 7,86 (s, 1H), total of 8.74 (IRTP., 1H).

In 30 ml of anhydrous N,N-dimethylformamide was dissolved 4.0 g (16,9 millimoles) of 4-isopropyl-5-iodine-1H-imidazole (4b), and then added 4.68 g (33,9 mm) 3.5-dimethylthiophenol and 2.1 g (52,5 mm) of 60% sodium hydrate. The resulting mixture was heated for 7 hours at a temperature of 140oC. Then N, N-dimethylformamide drove away under reduced pressure, and after adding dry ice residue was extracted with methylene chloride. The organic layer was washed with water and dried with sodium sulfate. After removal of the solvent under reduced pressure, the residue was separated into fractions by chromatography on silica gel (3% methanol/methylenechloride). Polyuretane the crude substance was recrystallized from ethyl acetate/diisopropyl ether, the result of which was obtained 2.2 g (yield 53%) of 5-(3,5 - dimethylphenyl)-4-isopropyl-1H-imidazole (X = Y = Me) (9).

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J = 7,0 Hz, 6H), are 2.19 (s, 6H), 3,25 (Sept., 1H), of 6.52 (s, 2H), 6,72 (s, 1H), 7,66 (s, 1H), 8.30 (width, 1H).

In 10 ml of anhydrous N,N-dimethylformamide was dissolved 1.0 g (4.1 millimoles) of 5-(3,5-dimethylphenyl)-4-idrica sodium. After 5 minutes was added 690 mg (4.9 mm) under the conditions, and the mixture was stirred for ten minutes. The resulting reaction mixture was poured into ice water and was extracted with diethyl ether. The organic layer was washed with water and dried with sodium sulfate. After removal of the solvent under reduced pressure, the residue was separated into fractions by chromatography on dioxide aluminum (eluent: ethyl acetate/n-hexane 1:1). From the first fraction was allocated 833 mg (yield 79%) of 5-(3,5 - dimethylphenyl)-4-isopropyl-1-methyl-4H-imidazole (X = Y = Me) (10) in the form of an oily substance.

1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J = 6.8 Hz, 3H), 1.27mm (d, J = 6.8 Hz, 3H), 2,22 (s, 6H), 3,17 (Sept, 1H), 3,53 (s, 3H), to 6.57 (s, 2H), 6,76 (s, 1H), 7,65 (s, 1H).

From the polar fraction was obtained 201 mg (yield 19%) of methyl isomer position (10') in the form of an oily substance.

1H-NMR (CDCl3- TMS) million D.: 1,31 (d, J = 7.2 Hz, 6H), of 2.21 (s, 6H), 3,30 (Sept., 1H), to 3.67 (s, 3H), of 6.71 (s, 2H) 6.75 in (s, 2H), 7,42 (s, 1H).

In 16 ml of anhydrous tetrahydrofuran was dissolved 800 mg (3.1 millimoles) of 5-(3,5-dimethylphenyl)-4-isopropyl-1-methyl - 1H-imidazole (X = Y = Me) (10). The resulting solution was cooled to -78oC, and then in a nitrogen atmosphere for one drop was added 2.2 ml (of 1.66 mol) n-utility in n-hexane. Across the same temperature, The resulting reaction mixture was poured into ice water and was extracted with diethyl ether. The organic layer was washed with water and dried with sodium sulfate. After removal of the solvent under reduced pressure the residue was purified by chromatography on silica gel (ethyl acetate/n-hexane 1: 5), resulting in a received 644 mg (yield = 73%) of Compound 1-6. So pl.: 93-94oC.

1H-NMR (CDCl3- TMS) million D.: of 1.29 (d, J = 7,0 Hz, 6H), of 2.23 (s, 6H), 3,26 (Sept., 1H), 3,91 (s, 3H), 6,59 (s, 2H), for 6.81 (s, 1H), 9,83 (s, 1H).

Example 7

Synthesis of 5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole - 2-carbaldehyde (Compound 1-7)

Connection 1-7 was obtained by the synthesis method described in example 6 for Compounds 1-6. Obtained compound represented an oily substance.

1H-NMR (CDCl3- TMS) million D.: of 1.29 (d, J = 7,0 Hz, 6H), 3,19 (Sept., 1H), for 6.81 (m, 2H), 7,18 (m, 1H), 9,86 (s, 1H).

Example 8

Synthesis of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl - 1H-imidazol-2-yl]methanol (Compound 1-8)

In 4 ml of ethanol was dissolved 440 mg (1.3 millimoles) of 5-(3,5-dichlorophenylthio)-4 - isopropyl-1-methyl-1H-imidazole-2-carbaldehyde (Compound 1-6), and then was added 51 mg (1.3 millimoles) of sodium borohydride at room temperature. After incubation for 10 meisenholder. The organic layer was washed with water and dried with sodium sulfate. The solvent was concentrated under reduced pressure, then the residue was recrystallized from isopropyl ether/n-hexane, resulting in received 340 mg (yield 77%) of Compounds 1-8.

So pl.: 157-158oC.

1H-NMR (CDCl3-TMS) million D.: of 1.18 (d, J = 7,0 Hz, 6H), to 3.09 (Sept., 1H) and 3.59 (s, 3H), amounts to 4.76 (s, 2H), 4,76 (width,1H), for 6.81 (m, 2H), 7,12 (m, 1H).

Elemental analysis (C14H16Cl2N2OS):

Calculated (%): C 50,76 H 4,87 N 8,46

Found (%): C 50,81 H 4,92 N 8,44.

Example 9

Synthesis of [5-(3,5-dimethylphenyl)-4-isopropyl-1-methyl-1H-imidazol - 2-yl] methanol (Compound 1-9)

Connection 1-9 were obtained by the synthesis method described in example 8 for Compounds 1-8. So pl.: 131~133oC.

1H-NMR (CDCl3-TMS) mn d: 1,23 (d, J = 7,0 Hz, 6H), of 2.23 (s, 6H), 3,19 (Sept., 1H), to 3.58 (s, 3H) and 4.65 (s, 2H), 6.75 in (lat., 1H), 6,59 (s, 2H), 6,77 (s, 1H).

Example 10

Synthesis of oxime 5-(3,5-dimethylphenyl)-4-isopropyl-1-methyl - 1H-imidazole-2-carbaldehyde (Compound 1-10)

In 2 ml of ethanol was dissolved 50 g (0,17 millimoles) of 5-(3,5 - dimethylphenyl)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde (Compound 1-6), and then was added 36 mg (0.5 mm) of hydroxylamine hydrochloride and 43 mg (0.5 Ionoi mixture was added water, and the mixture was extracted with methylene chloride. The organic layer was washed with water and dried with sodium sulfate and then the solvent was concentrated under reduced pressure. The residue was washed with ethyl acetate to precipitate the product, which idea was filtered and received 32 mg (yield 60%) of Compounds 1-10. So pl.: 240-241oC.

1H-NMR (DMSO-d6-TMS) million D.: 1,14 (d, J = 6.8 Hz, 6H), 2,19 (s, 1H), 3.08 (Sept. , 1H), 3,69 (s, 3H), 6,60 (s, 2H), for 6.81 (s, 1H), 8,11 (s, 1H), 11,67 (s, 1H).

Example 11

Synthesis of hydrazone 5-(3,5-dimethylphenyl)-4-isopropyl-1-methyl - 1H-imidazole-2-carbaldehyde (Compound 1-11)

In 2 ml of ethanol was dissolved 50 mg (0,17 millimoles) of 5-(3,5 - dimethylphenyl)-4-isopropyl-1-methyl-1H-imidazole-2-carbaldehyde (Compound 1-6), and then was added 26 mg (0.5 millimoles) of hydrazine hydrate is added, and the mixture was stirred for 15 minutes at room temperature. To the obtained reaction mixture was added water, and then extracted with methylene chloride. The organic layer was washed with water, dried with sodium sulfate, and the solvent was concentrated under reduced pressure. The residue was washed with n-hexane to precipitate the product which was then filtered, and received 34 mg (yield 65%) of Compound 1-11. So pl.: 118-119oC.

1H-NMR (CDClexample 12

Synthesis of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl] Isopropylamine (Compound 1-12)

(1) To a solution of anhydrous N,N-dimethylformamide containing 2.70 g (15 millimoles) of 3,5-dichloraniline and 0.36 g (15 millimoles) of sodium hydroxide, with stirring, was added a 3.06 g (10 millimoles) of 5-iodine-2-isobutyryl-4-isopropylimidazole (8) at room temperature. The resulting mixture was stirred for 30 minutes at room temperature and then was stirred for three hours while heating at 150oC. the Reaction mixture was concentrated under reduced pressure, and the residue was extracted with a mixture of water and ethyl acetate. The organic layer was washed with water and dried with sodium sulfate, then the solvent was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate/n-hexane = 1:9), resulting in a received 1.70 g (yield 48%) [5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-2-yl] Isopropylamine (14) in the form of an oily substance.

1H-NMR (CDCl3- TMS) million D.: 1,25-1,35 (m, 18H), is 1.81 (s, 6H), 3,29 (Sept. , 1H), 3,89 (Sept., 1H), 6,98 (d, J = 1.8 Hz, 2H), 7,10 (m, 2H), 7,18 (m, 1H), 7,30 (m, 1H).

(2) In 10 ml of acetone was dissolved 340 mg (0,66 mm) [5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-millimol) of potassium carbonate and 191 mg (13,0 mm) under the conditions. The resulting mixture was stirred over night. The reaction mixture was concentrated under reduced pressure and then the residue was extracted with methylene chloride. The organic layer was washed with water and dried with sodium sulfate, and the solvent is kept at reduced pressure. The residue was purified by chromatography on silica gel (eluent: ethyl acetate/n-hexane = 1:9), resulting in a received 123 mg (yield 50%) of Compounds 1-12 in the form of an oily substance.

1H-NMR (CDCl3-TMS) million D.: of 1.23 (d, J = 5.6 Hz, 6H), of 1.26 (d, J = 5.6 Hz, 6H), 3,36 (Sept, 1H), 3,88 (s, 3H), 4.00 points (Sept., 1H), 6,80 (d, J = 1.8 Hz, 2H), 7,15 (t, J = 1.8 Hz, 1H).

Comparative example 1

Synthesis of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H - imidazol-2-yl]methanol (Compound 1-8)

(1) Benzyloxyacetaldehyde (2C) was synthesized by the method described in Synthetic Communications, 18, 359 (1988).

In 200 ml of acetonitrile was dissolved in 53 g (339 millimoles) of 2,2-dichloro-3-methylbutyraldehyde (1). To the resulting solution at a temperature of 0oC was added 45 g of benzyloxyacetaldehyde (2C) and 400 ml of an aqueous solution of ammonia (28%). Then the mixture was stirred at room temperature for 15 hours. The reaction mixture was concentrated under reduced pressure, and the residue was extracted with methylenechloride the filtrate was concentrated under reduced pressure, the result that was obtained 2-(benzoyloxymethyl)-4-isopropyl-1H-imidazole (3C). Output: 77 g (96,5%).

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J= 6.8 Hz, 6H), 2,89 (m, 1H), of 4.54 (s, 2H) br4.61 (s, 2H), 6,66 (s, 1H), 7,31 (s, 5H).

(2) In 250 ml methylenchloride was dissolved 70 g (304 mm) of 2-(benzoyloxymethyl)-4-isopropyl-1H-imidazole (3C). Venture to the obtained solution at a temperature of 0oC was added an aqueous solution obtained by dissolving 13 g of sodium hydroxide in 160 ml of water, and the mixture was stirred for five minutes. After this, at a temperature of 0oC was added a solution of iodine (49 g, 386 mm) in methylene chloride (350 ml) and methanol (150 ml) and the mixture was stirred at room temperature for 20 minutes. To the reaction mixture were added an aqueous solution of sodium sulfite, and the venture was extracted with methylene chloride. The extract was washed with saturated saline, dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure, resulting in a received 2-benzoyloxymethyl - 5-iodine-4-isopropyl-imidazole (4C). The output 93 g (85,5%).

1H-NMR (CDCl3- TMS) million D.: of 1.20 (d, J = 7,0 Hz, 6H), 2,98 (m, 1H), of 4.54 (s, 2H), 4,57 (s, 2H), 7,31 (s, 5H).

(3) In 100 ml of dimethyl sulfoxide was dissolved 23 g (65 mm) 2-benzyloxyethyl, and then 14 g (39 millimoles) of di-3,5 - dichlorobenzaldehyde. The resulting mixture was stirred under heating at a temperature of 60oC for five hours. Then the reaction mixture was poured into ice water and was extracted twice with ethyl ether. The combined organic layer was twice washed with water and dried with sodium sulfate, then the solvent is kept at reduced pressure. The resulting residue was dissolved in ethanol and added to 5.85 g (65 millimoles) of oxalic acid. Selected so salt was collected by filtration, neutralized by adding aqueous ammonia and extracted with ethyl acetate. The organic layer was twice washed with water and dried with sodium sulfate. The solvent is kept at reduced pressure. The residue was washed with isopropyl alcohol, resulting in received 20 g (yield 86%) of 2-benzoyloxymethyl-5- (3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole (16A).

1H-NMR (CDCl3-TMS) million D.: 1,22 (d, J = 7.2 Hz, 6H), 3,64 (Sept., 1H), to 4.62 (s, 2H), 4,67 (s, 2H), 6,92 (Shir.s, 2H), 7,07 (Shir.s, 1H) of 7.36 (s, 5H), 9,2 (W, 1H).

(4) In 50 ml of anhydrous tetrahydrofuran was dissolved 15 g (44 millimoles) of 2-benzoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole (16A). To the resulting cooled solution at the mg of tetrabutylammonium bromide. After removal from the water bath with ice and the mixture was stirred for one hour. The resulting reaction mixture was concentrated under reduced pressure, then the residue was neutralized with hydrochloric acid and slightly podslushivaet by adding sodium bicarbonate, and then was extracted twice with ethyl acetate. The combined organic layer was washed with water and dried with sodium sulfate. After removal of the solvent under reduced pressure, the residue was separated into fractions by chromatography on silica gel (eluent: 3% ethyl acetate in methylene chloride). From the first fraction was obtained 3.5 g (yield 22%) of the target isomer position (17A') in the form of an oily substance. From the second fraction was obtained 10.4 g (yield 67%) target 2-benzoyloxymethyl-5-(3,5-dichlorophenylthio)-4 - isopropyl-1-methyl-1H-imidazole (17A) in the form of an oily substance.

(17a'):1H-NMR (CDCl3-TMS) million D.: of 1.30 (d, J = 7.2 Hz, 6H), 3,19 (Sept. , 1H), 3,66 (s, 3H), 4,55 (s, 2H), of 4.66 (s, 2H), 6,97 (d, J = 1.8 Hz, 2H), 7,05 (t, J = 1.8 Hz, 1H), 7,31-7,40 (m, 5H).

(17a)1H-NMR (CDCl3- TMS) million D.: of 1.26 (d, J=7,0 Hz, 6H), 3,12 (Sept. , 1H), 3,51 (s, 3H), 4,55 (s, 2H), 4,70 (s, 2H), 6,79 (d, J = 1.8 Hz, 2H), 7,11 (t, J = 1.8 Hz, 1H), 7,31-7,38 (m, 5H).

(5) In 20 ml of ethanol was dissolved 10.4 g (of 29.3 mmol) 2-benzoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl under reflux for 3 hours. Then this reaction mixture was concentrated under reduced pressure and the resulting residue was neutralized with an aqueous solution of sodium bicarbonate and was extracted with ethyl acetate. The organic layer was washed with water and dried with sodium sulfate, and the solvent is kept under reduced pressure; the residue was washed with isopropyl alcohol and got to 7.1 g (yield 92%) of target compound [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]methanol (Compound 1-8).

So pl. 157-158oC.

1H-NMR (CDCl3-TMS, m D.: of 1.18 (d, J = 7,0 Hz, 6H), to 3.09 (Sept., 1H) and 3.59 (s, 3H), amounts to 4.76 (s, 2H), 4,76 (width, 1H), for 6.81 (m, 2H), 7,12 (m, 1H);

Elemental analysis (C14H16Cl2N2OS)

Calculated: (%) C 50,76 H 4,87 N 8,46

Found: (%) C 50,81 H 4,92 N 8,44

Comparative example 2

Synthesis of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol - 2-yl] methanol (Compound 1-8)

(1) 1-p-methoxybenzylamine synthesized by the method described in Synthetic Communications, 18, 359 (1988). This compound (205,5 g, 0,968 mol) was dissolved in 1060 ml of methylene chloride. To the solution drop by drop) was added an aqueous solution (1883 ml) periodate sodium (269 g) at room temperature, and the mixture was stirred over night. This reaction mixture was diluted with 200 milliliters of igenom pressure, as a result, we received 175 g (yield 100%) p-methoxysalicylaldehyde (2d) in the form of an oily substance.

1H-NMR (CDCl3- TMS) million D.: 3,81 (s, 3H), 4,07 (s, 2H), 4,57 (s, 2H), 6.89 in-6,92 (m, 2H), 7,28-7,31 (m, 2H), 9,71 (s, 1H).

(2) In 970 ml of acetonitrile was dissolved in 175 g (0,968 mol) of p-methoxysalicylaldehyde (2d), and then added 150 g (0,968 mol) of 2,2-dichloro-3-methylbutyraldehyde (1). Then, while cooling with ice, one drop was added to 1300 ml of 28% aqueous ammonia solution. After complete addition, the mixture was left for 4 days at room temperature. Then this reaction mixture was concentrated under reduced pressure and extracted with methylene chloride. The organic layer was washed with saturated saline solution and dried with magnesium sulfate, and the solvent is kept at reduced pressure. The crude product was dissolved in ethyl acetate. To this solution was added a solution of oxalic acid (89,8 g, 0,968 mol) in ethyl acetate (70 ml) and the resulting oxalate was collected by filtration followed by washing with ethyl acetate. This oxalate neutralize 2 N sodium hydroxide and was extracted with ethyl acetate. The organic layer was washed with water and dried with magnesium sulfate. The solvent is then drove away when lower is in the form of an oily substance.

1H-NMR (CDCl3- TMS) million D.: 3,81 (s, 3H), 4,07 (s, 2H), 4,57 (s, 2H), 6.89 in-6,92 (m, 2H), 7,28-7,31 (m, 2H), 9,71 (s, 1H).

(3) In methylene chloride (60) and methanol (660 ml) was dissolved in 165 g (0.67 mol) of 4-isopropyl-2-(p-methoxybenzyloxy)-1H - imidazole (3d), and then was added 170 g of solid iodine. Then, while cooling with ice, drop by drop) was added an aqueous solution obtained by dissolving 27,3 g (0.67 mol) of sodium hydroxide in 85 ml of water. After adding one drop of the reaction mixture is stirred 1.5 hours at room temperature. This reaction mixture was extracted with methylene chloride, and the organic layer was washed with an aqueous solution of sodium sulfite and dried with anhydrous magnesium sulfate. The solvent is then drove away under reduced pressure, and the residue was washed with isopropyl ether and collected by filtration, resulting in received of 209.5 g (yield 81%) of 5-iodo-4-isopropyl-2-(p-methoxybenzyloxy)-1H - imidazole (4d).

So pl. 78-79oC.

1H-NMR (CDCl3- TMS) million D.; 1,20 (d, J=7,0 Hz, 6H), 2,99 (Sept., 1H), 3,81 (s, 3H), of 4.49 (s, 2H), 4,56 (s, 2H), to 6.88 (d, J=8.6 Hz, 2H), 7,25 (d, J=8.6 Hz, 2H), 9,18 (Shir.s, 1H).

(4) In 140 ml of dimethyl sulfoxide added 30 g (84 mmol) of di-3,5-dichlorobenzaldehyde, and of 1.34 g (168 mmol) of powder hydride Lite-isopropyl-2-(p-methoxybenzyloxy)-1H-imidazole (4d). After complete addition, the resulting mixture was stirred for 45 minutes under heating at 60oC. This reaction mixture was poured into ice water and was extracted twice with ethyl ether. The collected organic layer twice washed with water and dried with magnesium sulfate, and the solvent is kept at reduced pressure. The residue was dissolved in ethyl acetate and the solution was added oxalic acid (13.8 g, 65 mmol) in ethyl acetate (140 ml). The separated salt was collected by filtration and washed with about 100 milliliters of ethyl acetate. Then this salt was neutralized with 2 N NaOH and was extracted with diethyl ether. The organic layer was washed twice with water and dried with magnesium sulfate, and the solvent is kept under reduced pressure, resulting in a received 51 g (yield 76%) of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxy)-1H-imidazole (16b).

So pl. 96 - 97oC.

1H-NMR (CDCl3) million D.: 1,21 (d, J = 7,2 Hz, 6N), 3,18 (Sept., 1H), 3,81 (s, 3H), of 4.54 (s, 2H), with 4.64 (s, 2H), 6,88-6,92 (m, 4H), 7,07 (m, 1H), 7,26-7,30 (m, 2H).

Elemental analysis of C21H22Cl2N2O2S

Calculated (%): 57,67 N 5,07 Cl 16,21 N 6,40 S 7,33

Found (%): 57,62 N 5,09 Cl 16,32 to 6.43 N S 7,27

(5) In 25 ml of dry N,N-dimethylformamide was dissolved 11,0 g (25 is ol) of powdered potassium carbonate. After this was added 3,90 g (27.7 mmol) under the conditions, and the resulting mixture was stirred for 8 hours at room temperature. This reaction mixture was concentrated under reduced pressure, and the residue was diluted with water and was exteremely diethyl ether. The organic layer was washed with water and dried with magnesium sulfate. The solvent is kept under reduced pressure, and the residue was filtered through chromatography on silica gel (ethyl acetate:methylene chloride = 1: 9). From the first fraction was obtained 1.7 g (yield 15%) of the desired isomer position (17b') in the form of an oily substance. From the subsequent fractions were obtained 9,14 g (yield 80%) target 5-(3,5-dichlorophenylthio)-1-methyl-4-isopropyl-2- (p-methoxybenzyloxy)-1H-imidazole (17b).

So pl. 79-80oC.

(17b')1H-NMR (CDCl3- TMS) million D.: of 1.30 (d, J = 7.2 Hz, 6H), 3,18 (Sept. , 1H), to 3.64 (s, 3H), of 3.80 (s, 3H), 4,48 (s, 2H), with 4.64 (s, 2H), 6,84-7,27 (m, 7H).

(17b)1H-NMR (CDCl3-TMS) million D.; of 1.26 (d, J = 7,0 Hz, 6H), 3,12 (Sept. , 1H), 3,51 (s, 3H), of 3.80 (s, 3H), 4,48 (s, 2H), of 4.66 (s, 2H), 6,79-7,27 (m, 7H).

(6) In 45 ml of ethanol was dissolved 9,10 g (20,1 mmol) 5-(3,5-dichlorophenylthio)-1-methyl-4-isopropyl-2-(p-methoxybenzyloxy)- 1H-imidazole (17b), and then added to 90 ml of 6 N hydrochloric acid, and the resulting mixture was heated to reverse this b is anola, and the rest, forming two layers, two times were extracted with n-hexane to remove p-methoxybenzylamine. The aqueous layer was extracted with methylene chloride, and the extract was neutralized with an aqueous solution of sodium bicarbonate and dried with magnesium sulfate. The solvent is then drove away under reduced pressure, and the residue was washed with isopropyl ether, which was obtained 6.3 g (yield 95%) [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl] methanol (12 = Connection 1-8).

So pl. 157-158oC.

1H-NMR (CDCl3-TMS) million D.; of 1.18 (d, J = 7,0 Hz, 6H), to 3.09 (Sept., 1H) and 3.59 (s, 3H), amounts to 4.76 (s, 2H), 4,76 (width, 1H), for 6.81 (m, 2H), 7,12 (m, 1H).

Elemental analysis (C14H16Cl2N2OS)

Calculated (%): C 50,76 H 4,87 N 8,46

Found (%): C 50,81 H 4,92 N 8,44.

Example 13

Synthesis of [5-(3-chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]methanol (Compound 1-13)

(1) 5-(3-chlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxy)-1H-imidazole (16C) was obtained by a method described in Comparative example 2 (1) - (4).

Oxalate: so pl. 124-125oC.

1H-NMR (CDCl3-TMS) million D.: 1,21 (d, J=7,0 Hz, 6H), 3,20 (Sept., 1H), a 4.53 (s, 2H), 4,63 (s, 2H), 6.89 in (d, J= 8.6 Hz, 2H), 7,27 (d, J=8.6 Hz, 2H), 6.90 to-7,20 (m, 4H).

Elemental analysis (C22H25/BR>(2) From 5-(3-chlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxy)-1H-imidazole (16C) by the method described in Comparative example 2 (5) was obtained 2-(p-methoxybenzyloxy)-5-(3-chlorophenylthio)-1-methyl-4-isopropyl-1H-imidazole (17c) and its isomer provisions (17c') with yields of 46% and 8%, respectively.

(17c')1H-NMR (CDCl3-TMS) million D. : of 1.29 (d, J = 7,0 Hz, 6H), is 3.21 (Sept, 1H), 3,63 (s, 3H), of 3.80 (s, 3H), 4,48 (s, 2H), to 4.62 (s, 2H), 6.87 in (d, J = 8.6 Hz, 2H), 7,25 (d, J = 8.6 Hz, 2H), 6.90 to~7,20 (m, 4H).

(17c)1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J = 7.2 Hz, 6H), 3.15 in (Sept. , 1H), 3,50 (s, 3H), of 3.80 (s, 3H), 4,48 (s, 3H) and 4.65 (s, 3H), 6,86 (d, J = 8.6 Hz, 2H), 7,25 (d, J = 8,8 Hz, 2H), 6.75 in-7,20 (m, 4H).

(3) From 2-(p-methoxybenzyloxy)-5-(3-chlorophenylthio)-1-methyl - 4-isopropyl-1H-imidazole (17c) by the method described in Comparative example 2 (6), was obtained [5-(3-chlorophenylthio)-4-isopropyl-1-methyl-1H - imidazol-2-yl]methanol (Compound 1-13).

1H-NMR (CDCl3-TMS) million D.: of 1.18 (d, J= 7.2 Hz, 6H), of 3.12 (Sept, 1H), to 3.58 (s, 3H), and 4.75 (s, 2H), 6,70 - 7,25 (m, 4H).

Elemental analysis (C14H17ClN2OS):

Calculated (%): C 56,65 H 5,77 Cl 11,94 N 9,43 S 10,80

Found (%): C 56,81 H 5,78 Cl 11,88 N 9,16 S 10,47

Example 14

Synthesis of [4-Isopropyl-1-methyl-5-(3-nitrophenylthio)-1H-imidazol - 2-yl] methanol (Compound 1-14)

(1) 4-Isopropyl-2-(p-methoxybenzyl the x2">

1H-NMR (CDCl3-TMS) million D.; 1,22 ( d, 6N), 3,21 (Sept., 1H), 3,81 (s, 3H), 4,55 (s, 2H), with 4.64 (s, 2H), make 6.90 (d, J = 8.6 Hz, 2H), 7,29 (d, J = 8.6 Hz, 2H), 7,30-of 8.00 (m, 4H).

(2) the Method described in Comparative example 2 (17c), was obtained 4-isopropyl-2-(p-methoxybenzyloxy)-1-methyl - 5-(3-nitrophenylthio)-1H-imidazole (17d). Outputs 4-isopropyl-2-(p - methoxybenzyloxy)-1-methyl-5-(3-nitrophenylthio)-1H - imidazole (17d) and its isomer (17d') was 58% and 7%, respectively.

(17d') oily substance1H-NMR (CDCl3- TMS) million D.: 1,31 (d, J = 7,0 Hz, 6H), 3,21 (Sept., 1H), to 3.67 (s, 3H), of 3.80 (s, 3H), of 4.49 (s, 2H), 4,63 (s, 2H), to 6.88 (d, J = 8.6 Hz, 2H), 7,26 (d, J = 8.6 Hz, 2H), 7,30-of 8.00 (m, 4H).

(17d) so pl. 89~90oC.

1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J = 7,0 Hz, 6H), 2,14 (Sept., 1H), 3,80 (s, 3H), 4,50 (s, 2H), 4,67 (s, 2H), 6.87 in (d, J = 8.6 Hz, 2H), 7,25 (d, J = 8.6 Hz, 2H), 7,41 (t,J = 7,8 Hz, 1H), 7,83 (t, J = 2.0 Hz, 1H), 7,98 (m, 1H).

Elemental analysis (C22H25N3O4S):

Calculated (%): C 61,81 of 5.89 H N 9,83 S 7,50

Found (%): C 61,78 H 5,86 N 9,80 S OF 7.48

(3) Connection 1-14 was prepared from 4-isopropyl-2-(p-methoxybenzyloxy)-1-methyl-5-(3-nitrophenylthio)-1H-imidazole (17d) by the method described in example 2 to obtain Compounds 1-8.

1H-NMR (CDCl3-TMS) million D.: 1,19 (d, J = 6.8 Hz, 6H), 3,12 (Sept., 1H), 3,61 (s, 3H), of 4.77 (s, 2 Prov.-butyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H - imidazol-2-yl] methanol (Compound 1-15)

The method described in Comparative example 2 for the synthesis of 5-(3,5 - dichlorophenylthio)-1-methyl-4-isopropyl-2-(p-methoxybenzyloxy)- 1H-imidazole (17b), was obtained 2-(benzoyloxymethyl)-1-n-butyl-5- (3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole (e). Outputs 2-(benzoyloxymethyl)-1-n-butyl-5-(3,5-dichlorophenylthio)-4-isopropyl - 1H-imidazole (e) and its isomer provisions (e') were 91% and 6%, respectively.

(E') oily substance1H-NMR (CDCl3- TMS) million D.: of 0.93 (t, J = 7.2 Hz, 3H), of 1.33 (d, J = 7.2 Hz, 6H). 1,58 is 1.75 (m, 4H), 3,01 (Sept., 1H), 3,90-3,98 (m, 2H), of 4.54 (s, 2H) and 4.65 (s, 2H), 6,92 (s, 2H),? 7.04 baby mortality (s, 1H), 7,24 and 7.36 (m, 5H);

(E) an oily substance1H-NMR (CDCl3-TMS) million D.: 0,80 (t, J = 7.0 Hz, 3H), 1,25 (d, J = 7,0 Hz, 6H), of 1.1-1.3 (m, 2H), 1,42~1,60 (m, 2H), 3,09 (Sept., 1H), 3,84-to 3.92 (m, 2H), 4,55 (s, 2H), 4,67 (s, 2H), 6,79 (d, J = 2 Hz, 2H), 7,10 (t, J = 2 Hz, 1H), 7,30-7,39 (m, 5H).

Connection 1-15 was obtained from 2-(benzoyloxymethyl)-1-n-butyl - 5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole (e) by the method described in Comparative example 2 for the synthesis of Compounds 1-8. T. p. 104-106oC.

1H-NMR (CDCl3-TMS) million D.: 0,86 (t, J = 7.4 Hz, 3H), of 1.17 (d, J = 6.8 Hz, 6H), 1,20-1,40 (m, 2H), 1,50~of 1.65 (m, 2H), 3,06 (Sept., 1H), 3,92-4,00 (m, 2H), and 4.75 (s, 2H), 5,70 (s, 2H), 6,80 (d, J = 1.8 Hz, 2H), 7,11 (t, J = 1.8 Hz, 1H).

Example 16

Synthesis of [1-benzyl-5-(3,5-dichlorophenylthio (1.00 mmol) of 5-(3,5-dichlorophenylthio)-4-isopropyl - 2-(p-methoxybenzyloxy)-1H-imidazole (16b), and then stirring at room temperature, was added 205 mg (1.20 mmol) of benzylbromide, 48 mg (1.2 mmol) of sodium hydroxide and 5 mg (0.015 mmol) of tetrabutylammonium bromide, and the mixture was stirred at the same temperature for 3 hours. This reaction mixture was concentrated under reduced pressure, and the residue was diluted with water and extracted with methylene chloride. The organic layer was washed with water and dried with sodium sulfate. The solvent is kept under reduced pressure, and the oily residue was fractionally using chromatography on silica gel (ethyl acetate:methylene chloride = 1: 9). From the first fraction was obtained 33 mg (yield of 6.5%) of the desired isomer provisions 17f'). From the subsequent fractions were obtained 450 mg (yield 88%) 1 - beisel-5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p - methoxybenzyloxy)-1H-imidazole (17f).

(17f') oily substance1H-NMR (CDCl3- TMS) million D.: of 1.28 (d, J = 6.6 Hz, 6H), 2,95 (Sept., 1H), 3,79 (s, 3H), 4,50 (s, 2H), 4,55 (s, 2H), 5,28 (s, 2H), 6,83 (d, J = 6 Hz, 2H), 6,94-to 6.95 (m, 3H) 7,06 (m, 3H), 7,17 (d, J = 5.8 Hz, 2H), 7,26-7,40 (m, 4H).

(17f) an oily substance1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J=6.6 Hz, 6H), 3,13 (Sept., 1H), 3,80 (s, 3H), 4,47 (s, 2H), br4.61 (s, 2H), by 5.18 (s, 2H), 6,63 (d, J=1.6 Hz, 2H), 6,83 (d, J=2 Hz, 2H), 6.90 to-6,93 (m, 2H), 6,99 (s, 1H), 7,11-7,21 (m, 4H), 7,26 (s, 4H).

In 25 ml of masala (17f), and then stirring at room temperature, was added 12.5 ml 6 H hydrochloric acid, and the mixture was stirred for 3 hours at 60oC. This reaction mixture was concentrated under reduced pressure, the residual solution was neutralized with saturated aqueous sodium bicarbonate solution to obtain a weakly basic solution and was extracted with methylene chloride. The extract was washed with water and dried with magnesium sulfate, and the solvent was concentrated under reduced pressure. The residue was led from n-hexane and collected by filtration, which was obtained 1.0 g (yield 92%) of [1-benzyl-5-(3,5 - dichlorophenylthio)-4-isopropyl-1H-imidazol-2-yl] methanol (Compound 1-16). So pl. 121-124oC.

1H-NMR (CDCl3- TMS) million D.: of 1.28 (d, J=6.9 Hz, 6H), 3.15 in (Sept., 1H), 4,79 (s, 2H, in), 5.25 (s, 2H), only 6.64 (d, J= 1.2 Hz, 2H), 6,9-7,0 (m, 3H), 7.18 in-7,26 (m, 4H).

Example 17

Synthesis of [1-allyl-5-(3-chlorophenylthio)-4-isopropyl-1H-imidazol - 2-yl]methanol (Compound 1-17)

(1) In 10 ml of anhydrous tetrahydrofuran was dissolved 744 mg (2.00 mmol) of 2-(benzoyloxymethyl)-5-(3-chlorophenylthio)-4-isopropyl-1H - imidazole (16e), and then was added 410 mg (2,40 mmol) allylbromide, 96 mg (2,40 mmol) of sodium hydroxide and 5 mg (0.015 mmol) of tetrabutylammonium bromide, stirring at room shall have centriole under reduced pressure, the residue was extracted with methylene chloride, and the organic layer was washed with water and dried with sodium sulfate. The solvent was concentrated under reduced pressure, and the oily residue was fractionally using chromatography on silica gel (ethyl acetate: methylene chloride = 1:9). From the first fraction was obtained 50 mg (yield of 6.7%) of the desired isomer provisions (17g'), then received 480 mg (yield 58%) of 1-allyl-2-benzoyloxymethyl-5-(3-chlorophenylthio)-4-isopropyl - 1H-imidazole (1g).

(17g') oily substance;1H-NMR (CDCl3-TMS) million D.: of 1.30 (d, J= 7.2 Hz, 6H), 3.00 today (Sept., 1H), a 4.53 (s,2H), of 4.66 (s, 2H), 4,67 (d, J=6.3 Hz, 2H), a 4.83 (d, J=17,4 Hz, 1H), total of 5.21 (d, J=11,1 Hz, 1H), 5,85-5,95 (m, 1H), 6,97? 7.04 baby mortality (m, 3H), 7,09-7,14 (m, 1H), 7,25-7,40 (m, 5H).

(17g) an oily substance; 1H-NMR (CDCl3- TMS) million D.: of 1.26 (d, J= 6.9 Hz, 6H), 3,13 (Sept., 1H), of 4.54 (s, 2H), 4,55 with 4.65 (m, 2H), 4,79 (s, 2H), 4,82 (d, J=18.3 Hz, 1H), free 5.01 (d, J=11,4 Hz, 1H), ceiling of 5.60-of 5.75 (m, 1H), for 6.81 (d, J= 10.5 Hz, 2H), 6,93 (s, 1H), 7,05 is 7.50 (m, 2H), 7,30-7,40 (m, 5H).

(2) In 5 ml of methylene chloride was dissolved 470 mg (1.13 mmol) of 1 - allyl-2-benzoyloxymethyl-5-(3-chlorophenylthio)-4-isopropyl-1H - imidazole (17g), cooling up to -40oC, and then, stirring was added 0.7 ml (1,36 mmol) methylenechloride solution trichloride boron (1.94 mol) and the resulting mixture was exchanged within 30 minutes. To this reaction CME is Oh was washed with water and dried with sodium sulfate. The solvent was concentrated under reduced pressure, and the residue was separated into fractions by chromatography on silica gel (ethyl acetate:methylene chloride = 1:4). From the first fraction was obtained 50 mg (yield 13%) of 1-allyl-2-chloromethyl-5-(3-chlorophenylthio)-4 - isopropylimidazole (28a) in the form of an oily substance, and then 155 mg (yield 43%) of Compound 1-17.

So pl. 84-86oC.

(28a)1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J= 6.9 Hz, 6H), and 3.16 (Sept., 1H), 4,66-and 4.68 (m, 2H), 4,69 (s, 2H), to 4.98 (d, J=18 Hz, 1H), 5,12 (d, J=12,6 Hz, 1H), 5,65-5,80 (m, 1H), 6,8 (d, J=10.5 Hz, 1H), 6,95 (s, 1H), 7,1-7,2 (m, 2H).

Connection 1-171H-NMR (CDCl3-TMS) million D.: of 1.23 (d, J=6.8 Hz, 6H), and 3.16 (Sept. , 1H), br4.61-of 4.66 (m, 2H), 4,74 (s, 2H), 4.92 in (d, J=18 Hz, 1H), 5,10 (d, J=12 Hz, 1H), 5,6 - 5,8 (m, 1H), 6,80-6,84 (m, 1H), 6,95 (t, J=2.7 Hz, 1H), 7,1-7,2 (m, 2H).

Example 18

Synthesis of [5-(3,5-dichlorophenylthio)-1-dodecyl-4-isopropyl-1H - imidazol-2-yl] methanol (Compound 1-18)

(1) 5-(3,5-dichlorophenylthio)-1-dodecyl-4-isopropyl-2-(p - methoxybenzyloxy)-1H-imidazole (17h) was obtained by the synthesis method described in example 16 for (17f) (yield 43%).

(17h) an oily substance1H-NMR (CDCl3- TMS) million D.: of 0.87 (t, J= 6.0 Hz, 3H), of 1.26 (d, J=6.9 Hz, 6H), 1.1 to 1.4 (m, 18H), 1.5 a (width, 2H), 3,07 (Sept. , 1H), 3,81 (s, 3H), 3,85-3,90 (m, 2H), 4,48 (s, 2H), with 4.64 (s, 2H), 6,80 (s, 2H), 6.87 in (d, J=8,4 Hz, 2H), 7,11 (s, 1H), 7,27 (s, 2H).

the Ola (17h), described in example 16 for the synthesis of Compounds 1-16. (Yield 68%).

1H-NMR (CDCl3-TMS) million D. : 0,89 (t, J=7.5 Hz, 3H), of 1.21 (d, 6H), 1,2-1,3 (m, 18H), 1,6 (width, 2H), 3,10 (Sept., 1H), 3,92 (t, J=10 Hz, 2H), amounts to 4.76 (s, 2H), PC 6.82 (d, J=1.6 Hz, 2H), 7,12 (t, J=1.6 Hz, 1H).

Example 19

Synthesis of [1-allyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol - 2-yl] methanol (Compound 1-19)

(1) 1-Allyl-5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p - methoxybenzyloxy)-1H-imidazole (17i) was obtained by the method described in example 16 synthesis of compound (17f). Outputs (17i) and its isomer provisions (17i') was 83% and 8%, respectively.

(17i') oily substance;1H-NMR (CDCl3- TMS) million D.: of 1.29 (d, J= 7.5 Hz, 6H), was 3.05 (Sept, 1H), 3,80 (s, 3H), of 4.46 (s, 2H), 4,58 (s, 2H), 4,62-4,7 (m, 2H), 4,82 (d, J=15 Hz, 1H), 5,22 (d, J=11 Hz, 1H), of 5.82 is 5.98 (m, 1H), 6.87 in (d, J=6 Hz, 2H).

(17i) an oily substance;1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J= 7.2 Hz, 6H), 3,10 (Sept., 1H), 3,81 (s, 3H), 4,47 (s, 2H), to 4.62 (s, 2H), 4,57-to 4.62 (m, 2H), 4,82 (d, J=18 Hz, 1H), to 5.03 (d, J=10 Hz, 1H), 5,58-5,80 (m, 1H), 6.87 in (d, J=2 Hz, 2H), 6.8 or 6.9 (m, 2H), and 7.1 (t, J=3,4 Hz, 1H), of 7.23 (s, 2H).

(2) [1-Allyl-4-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol - 2-yl] methanol (Compound 1-19) was obtained from 1-allyl-5- (3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxy)- imidazole (17i) by the method described in example 16 synthesis With the l2OS):

Calculated (%): C 53,79 H 5.08, N 7,75 Cl 19,85 S 8,90

Found (%): C 53,68 H 5,16 N 7,75 Cl 19,57 S 8,99

Example 20

Synthesis of [1-benzyl-5-(3-chlorophenylthio)-4-isopropyl-1H-imidazol-2 - yl]methanol (Compound 1-20).

(1) 1-Benzyl-5-(3-chlorophenylthio)-4-isopropyl-2-benzoyloxymethyl - 1H-imidazole (17j) was obtained by the method described in example 17 synthesis of compound (17g). Outputs connection (17j) and its isomer provisions (17j') was 88% and 3%, respectively.

(17j') oily substance;1H-NMR (CDCl3-TMS) million D.: 1,17 (d, J=7 Hz, 6H), 2,97 (Sept., 1H), a 4.53 (s, 2H), 4,60 (s, 2H), and 5.30 (s, 2H), 6,9-7,2 (m, 8H), of 7.2 to 7.4 (m, 5H).

(17j) oily substance; 1H-NMR (CDCl3-TMS) million D.; of 1.28 (d, J=7 Hz, 6H), and 3.16 (Sept., 1H), 4,51 (s, 2H), 4,58 (s, 2H), 5,19 (s, 2H), 6,72-to 6.80 (m, 3H), 6,88-6,93 (m, 2H), 7,02-7,05 (m, 2H), 7,14~7,26 (m, 2H), 7.23 percent-to 7.32 (m, 5H).

(2) 2- [1-Benzyl-5-(3-chlorophenylthio)-4-isopropyl-1H-imidazol - 2-yl]methanol (Compound 1-20) was obtained from 1-benzyl-5-(3 - chlorophenylthio)-4-isopropyl-2-benzoyloxymethyl-1H-imidazole (17j) by the method described in example 17 for the synthesis of Compounds 1-17. (Yield 35%). So pl. 120-122oC.

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J=6.6 Hz, 6H), and 3.16 (Sept., 1H), 4,70 (s, 2H), with 5.22 (s, 2H), 6.75 in-PC 6.82 (m, 2H), 6.90 to-7,06 (m, 4H), 7,1-7,3 (m, 3H).

Elemental analysis (C20H21N2ClOS):

Facilediaper-5-(3-nitrophenylthio)-1H-imidazol - 2-yl]methanol (Compound 1-21)

(1) 1-Benzyl-5-(3-nitrophenylthio)-4-isopropyl-2-butylacetyl - 1H-imidazole (17K) was obtained by the method described in example 17 synthesis (17g). Outputs connection (17K) and its isomer provisions (17K') was 92% and 2%, respectively.

(17K') oily substance1H-NMR (CDCl3- TMS) million D.: 1,17 (d, J= 7.2 Hz, 6H), 2,96 (Sept., 1H), a 4.53 (s, 2H), 4,59 (s, 2H), and 5.30 (s, 2H), 6,98 (d, J=6,9 Hz, 2H) 7.23 percent-7,41 (m, 8H), 7,49 (d, J=9,3 Hz, 1H), 7,80 (t, J=1.8 Hz, 1H), 7,92 (d, J=10 Hz, 1H).

(17k) an oily substance1H-NMR (CDCl3- TMS) million D.: of 1.30 (d, J= 6.9 Hz, 6H), 3.15 in (Sept., 1H), 4,57 (s, 2H), 4,67 (s, 2H), with 5.22 (s, 2H), 6.90 to-6,93 (m, 2H),? 7.04 baby mortality-7,13 (m, 4H), 7,22 - 7,33 (m, 5H), 7,56 (t, J= 2.1 Hz, 1H), 7,82-7,86 (m, 1H).

(2) [1-Benzyl-4-isopropyl-5-(3-nitrophenylthio)-1H-imidazol-2-yl] methanol (Compound 1-21) was obtained from 1-benzyl-5-(3-nitrophenylthio)-4 - isopropyl-2-benzoyloxymethyl-1H-imidazole (17K) in a manner analogous to the method of synthesis of Compounds 1-17 described in example 17. (Yield 37%). So pl. 152-155oC.

As a by-product was obtained 1-benzyl-2-chloromethyl-5- (3-nitrophenylthio)-4-isopropyl-1H-imidazole (28b), (yield 9%).

(28b) an oily substance1H-NMR (CDCl3- TMS) million D.; of 1.29 (d, J= 6.6 Hz, 6H), 3.15 in (Sept., 1H), 4,63 (s, 2H), from 5.29 (s, 2H), 6.89 in-6,92 (m, 2H), 7,05-7,14 (m, 5H), 7,63-of 7.90 (m, 2H).

Connection 1-211H-NMR (CDCl3

Elemental analysis (C20H21N3O3S):

Calculated (%): C 62,64 H 5,52 N 10,96 S AT 8.36

Found (%): H 5,66 of 10.58 N S 8,05

Example 22

Synthesis of [1-allyl-4-isopropyl-5-(3-nitrophenylthio)-1H-imidazol - 2-yl] methanol (Compound 1-22)

(1) 1-Allyl-5-(3-nitrophenylthio)-4-isopropyl-2-benzyloxyethyl)- 1H-imidazole (17l') was obtained by the method described in example 17 synthesis (17g). Outputs connection (17l') and its isomer provisions (17l') was 82% and 9%, respectively.

(17I') oily substance1H-NMR (CDCl3-TMS) million D.: 1,31 (d, J= 7.2 Hz, 6H), 3.00 today (Sept., 3H), 4,55 (s, 2H), 4,63 (s, 2H), 4,69-to 4.73 (m, 2H), a 4.86 (dt, J=15 Hz, 2 Hz, 1H), 5,24 (dt, J=11 Hz, 2 Hz, 1H), 5,80-6,00 (m, 1H), 7,26-of 7.48 (m, 7H), 7,83 (t, J=2 Hz, 1H), 7,92 (dt, J=9 Hz and 1.4 Hz, 1H).

(17l') oily substance1H-NMR (CDCl3-TMS) million D.: of 1.27 (d, J= 7.2 Hz, 6H), 3,11 (Sept., 1H), 4,56 (s, 2H), 4,56-of 4.66 (m, 2H), of 4.66 (s, 2H), 5,55-of 5.75 (m, 1H), 7,19-the 7.43 (m, 7H), 7,83 (t, J=2 Hz, 1H), of 7.96 (dt, J=8,2 Hz, 1.2 Hz, 1H).

(2) Compound 1-22 received from (17l') in the same manner that was described in example 17 for the synthesis of Compounds 1-17. (Yield 37%). So pl. 117-120oC.

As a by-product was obtained 1-allyl-2-chloromethyl - 5-(3-nitrophenylthio)-4-isopropyl-1H-imidazole (28C). (Yield 11%).

(28C) an oily substance1.

Connection 1-221H-NMR (CDCl3-TMS) million D.: 1,24 (d, J=7.2 Hz, 6H), 3,14 (Sept., 1H), with 4.64 - 4,69 (m, 2H), 4,71 (s, 2H), 4,9 (d, J=19,8 Hz, 1H), 5,08 (d, J=12 Hz, 1H), 5,65-5,63 (m, 1H), 7.23 percent-7,26 (m, 1H), 7,42 (t, J=8,1 Hz, 1H), 7,87 (s, 1H), to 7.99 (d, J=9 Hz, 1H).

Elemental analysis (C16H19N3O3S):

Calculated (%): C 57,64 H 5,74 N 12,60 S 9,62

Found (%): C 57,45 Of 5.84 H N 12,70 S Was 9.33.

Example 23

Synthesis of [1-ethyl-4-isopropyl-5-(3-nitrophenylthio)-1H-imidazol-2 - yl]methanol (Compound 1-23)

(1) by the Method described in example 17 synthesis (17g), was obtained 1-ethyl-5-(3-nitrophenylthio)-4-isopropyl-2-benzoyloxymethyl-1H-imidazole (17m). Outputs connection (17m) and its isomer provisions (17m') was 89% and 12%, respectively.

(17m') oily substance 1H-NMR (CDCl3- TMS) million D.: 1,36 (d, J= 7.2 Hz, 6H), of 1.36 (t, J=6.9 Hz, 3H), of 3.07 (Sept., 1H), 4.09 to (sq, J=6,9 Hz, 2H), 4,57 (s, 2H), 4,67 (s, 2H), 7,26 was 7.45 (m, 7H), 7,86 (t, J=2.1 Hz, 1H), to $ 7.91 (dt, J=9 Hz, 1.2 Hz, 1H).

(17m) an oily substance 1H-NMR (CD-TMS) million D.: of 1.18 (d, J=7.5 Hz, 6H), of 1.26 (t, J=7.5 Hz, 3H), 3,12 (Sept., 1H), 3,99 (sq, J=7.5 Hz, 2H), 4,58 (s, 2H), 4,69 (s, 2H), 7,20 (DD, J= 8,1 Hz, 0.9 Hz, 1H), 7,30-7,42 (m, 6H), to 7.84 (d, J=2.1 Hz), of 7.96 (DD, J=8,1 Hz, 0.9 Hz, 1H).

(2) Compound 1-23 was obtained from 1-ethyl-5-(3-nitrophenylthio)-4 - isopropyl-2-benzoyloxymethyl-1H-imidazole (17m) in the same way that was used Educt was obtained 1-ethyl-2-chloromethyl - 5-(3-nitrophenylthio)-4-isopropyl-1H-imidazole (28d).

Exit 13%.

(28d) an oily substance1H-NMR (CDCl3- TMS) million D.: of 1.26 (d, J= 6.9 Hz, 6H), of 1.28 (t, J=7 Hz, 3H), of 3.12 (Sept, 1H), 4,03 (sq, J=7 Hz, 2H), 4,60 (s, 2H), 4.72 in (s, 2H), 7.18 in was 7.45 (m, 2H), 7,84-to 7.95 (m, 2H).

Connection 1-231H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J=6.9 Hz, 6H), 1,24 (t, J=7.2 Hz, 3H), 3,11 (Sept., 1H), 4,06 (sq, J=7.2 Hz, 2H), of 4.77 (s, 2H), 7,22 (d, J=11 Hz, 1H), 7,40 (t, J=7 Hz, 1H), 7,87 (t, J=2 Hz, 1H), 7,97 (DD. J=11 Hz, 1 Hz, 1H).

Elemental analysis (C15H19N3O3SH2O):

Calculated (%): C 55,44 of 6.02 H N 12,93 S 9,86

Found (%): C 55,36 H 6,90 N 12,91 S 9,70.

Example 24

Synthesis of [4-isopropyl-5-(3-nitrophenylthio)-1-n-propyl-1H-imidazol - 2-yl] methanol (Compound 1-24)

(1) by the Method described in example 17 synthesis (17g), received 2-benzoyloxymethyl-4-isopropyl-5-(3-nitrophenylthio)-1-n-propyl-1H - imidazole (17n). Outputs (17n) and its polymer provisions (17n') was 93% and 7.5%, respectively.

(17n') oily substance 1H-NMR (CDCl3- TMS) million D. as 0.96 (t, J= 10 Hz, 3H), of 1.34 (d, 7.2 Hz, 6H), a 1.7-1.8 (m, 2H), 3.04 from (Sept., 1H), 3.93-3,98 (m, 2H), 4,55 (s, 2H) and 4.65 (s, 2H), 7,26-the 7.43 (m, 7H), 7,83 (t, J=2.1 Hz, 1H), of 7.90 (DD, J=7.8 Hz, 1.2 Hz, 1H).

(17n) an oily substance1H-NMR (CDCl3- TMS) million D.; to 0.80 (t, J= 7.2 Hz, 3H), 1,25 (d, J=6.9 Hz, 6H), 1,5-of 1.62 (m, 2H), 3,11 (Sept., 1H), 3,84-to 3.89 (m, 2H), 4,57 (s, 2H), 4,67 (s, 2H), 7,18 (DD, J=4,8 shall simetal-4-isopropyl - 5-(3-nitrophenylthio)-1-n-propyl-1H-imidazole (17n) method, described in example 17 for the synthesis of Compounds 1-17. (Yield 65%). An oily substance.

1H-NMR (CDCl3-TMS) million D.; to 0.88 (t, J=7.2 Hz, 3H), 1,19 (d, J=6.9 Hz, 6H), 1,58 is 1.70 (m, 2H), 3,10 (Sept., 1H), 3,93 (t, J=7.2 Hz, 2H), amounts to 4.76 (s, 2H), 7,20 (d, J=9 Hz, 1H), 7,40 (t, J=8,1 Hz, 1H), 7,85 (t, J=2.1 Hz, 1H), of 7.97 (DD, J=11 Hz, J=0.9 Hz, 1H).

Example 25

Synthesis of 2-[5-(3,5-dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol - 2-yl] methanol (Compound 1-25)

(1) 5-(3,5-Dichlorophenylthio)-1-ethyl-4-isopropyl-2-(p - methoxybenzyloxy)-1H-imidazole (17o) was obtained by the method described in example 16 synthesis (17f). (Yield 35%). An oily substance.

1H-NMR (CDCl3-TMS) mn d: of 1.18 (t, J= 7.0 Hz, 3H), 1,25 (d, J=7,0 Hz, 6H), to 3.09 (Sept., 1H), 3,80 (s, 3H), 3.96 points (kV, J=7,0 Hz, 2H), 4,48 (s, 2H), with 4.64 (s, 2H), 6,80 (d, J=1.4 Hz, 2H), 6,85-6,89 (m, 2H), 7,11 (t, J=1,8, 1H), 7.24 to 7,28 (m, 2H).

(2) Connection 1-25 was obtained from 5-(3,5-dichlorophenylthio)-1-ethyl - 4-isopropyl-2-(p-methoxybenzyloxy)-1H-imidazole (17o) by the method described in Comparative example 2 for the synthesis of Compounds 1-8. (Yield 80%). So pl. 120-121oC.

1H-NMR (CDCl3-TMS) million D.: 1,17 (d, J=6.6 Hz, 6H), 1,25 (t, J=7.0 Hz, 3H), of 3.07 (Sept. , 1H), of 4.05 (t, J=7,0 Hz, 2H), amounts to 4.76 (s, 2H), 5,79 (width, 1H), for 6.81 (d, J=1.6 Hz, 2H), 7,11 (t, J=1.6 Hz, 1H).

Example 26

Synthesis of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-n-propyl-1H - imidazole-imidazole (17p) was obtained by way described in example 16 synthesis (17f). (Yield 41%). An oily substance.

1H-NMR (CDCl3-TMS) million D.: 0,81 (t, J=7,6 Hz, 3H), 1,24 (d, J=7,0, 6H), 1,51-of 1.64 (m, 3H), is 3.08 (Sept., 1H), 3,81 (s, 3H), 3,80-a 3.87 (m, 2H); 4,48 (s, 2H), 4,63 (s, 2H), 6,78 (d, J=8 Hz, 2H), 6,86-of 6.90 (m, 2H), 7,11 (t, J=1.8 Hz, 1H), 7.24 to 7,28 (m, 2H).

(2) Compound 1-26 was obtained from 5-(3,5-dichlorophenylthio)-4 - isopropyl-2-(p-methoxyethoxymethyl)-1-n-propyl-1H-imidazole (17p) by the method described in Comparative example 2 for the synthesis of Compounds 1-8. (Yield 72%). So pl. 104-107oC.

1H-NMR (CDCl3-TMS) million D.: 1,17 (d, J=6.6 Hz, 6H), 1,25 (t, J=7.0 Hz, 3H), of 3.07 (Sept. , 1H), of 4.05 (t, J=7,0 Hz, 2H), amounts to 4.76 (s, 2H), 5,79 (width, 1H), for 6.81 (d, J=1.6 Hz, 2H), 7,11 (t, J=1.6 Hz, 1H).

Elemental analysis (C16H20Cl2N2OS 0,1 H2O):

Calculated (%): C 53,22 H 5,64 N 7,76 S 8,88 Cl quintiles these figures were 19.63

Found (%): C 53,27 H 5,63 To 7.77 N S 8,89 Cl 19,96.

Example 27

Synthesis of [5-(3,5-dichlorophenylthio)-1,4-aminobutiramida-1H-imidazol - 2-yl]methanol (Compound 1-27).

(1) 5-(3,5-dichlorophenylthio)-1,4-aminobutiramida-2- (p-methoxybenzyloxy)-1H-imidazole (17q) was obtained by the method described in example 16 synthesis (17f). (Yield 43%).

1H-NMR (CDCl3-TMS) million D.; to 1.23 (d, J=7,0 Hz, 6H), of 1.42 (d, J=7.2 Hz, 6H), of 3.07 (Sept., 1H), 3,81 (s, 3H), 4,48 (s, 2H), 4,60-4,74 (m, 1H), 4,67 (s, 2H), 6,79 (d, J=1.8 Hz, 2H), 6,85-6,90 (methoxyethoxymethyl)-1H-imidazole (17q), described in comparative example 2 for the synthesis of Compounds 1-8. (Yield 64%). So pl. 136-137oC.

1H-NMR (CDCl3-TMS) million D.: 1,19 (d, J=6.6 Hz, 6H), of 1.45 (d, J=7,0 Hz, 6H), 2,99-3,13 (m, 1H), or 4.31 (width, 1H), 4,62-of 4.77 (m, 1H), 4,79 (s, 2H), 6,8 (d, J=1.4 Hz, 2H), 7,11 (d, J= 1.6 Hz, 1H).

Example 28

Synthesis of [1-ethyl-5-(3-chlorophenylthio)-4-isopropyl-1H-imidazol-2-yl] methanol (Compound 1-28).

(1) 2-Benzoyloxymethyl-5-(3-chlorophenylthio)-1-ethyl-4-isopropyl - 1H-imidazole (17r) was obtained by the method described in example 17 synthesis (17g).

1H-NMR (CDCl3-TMS) million D.: 1,17 (t, J=7.4 Hz, 3H), 1,25 (d, J=6.6 Hz, 3H), 3,13 (Sept., 1H), 3,98 (sq, J=7,4 Hz, 2H), 4,56 (s, 2H), 4,67 (s, 2H), 6,79-7,20 (m, 4H), 7.24 to 7,40 (m, 5H).

(2) Compound 1-28 was obtained from 2-benzoyloxymethyl-5- (3-chlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole (17r) by the method described in Comparative example 1 for the synthesis of Compounds 1-8. (Yield 64%). So pl. 99-100oC.

1H-NMR (CDCl3-TMS) million D.: 1,19 (d, J=6.6 Hz, 6H), 1,24 (t, J=7.0 Hz, 3H), 3,12 (Sept., 1H), 4,05 (sq, J=7,0 Hz, 2H), 4,77 (m, 2H), 6,78-7,19 (m, 4H).

Elemental analysis (C12H19ClN2OS0,15 H2O):

Calculated (%): C 57,46 H 6,20 N 8,93

Found (%): C 57,25 H 6,05 N 8,92.

Example 29

Synthesis of [5-(3-chlorophenylthio)-4-isopropyl-1-n-propyl-1H-imidazol - 2-yl] methanol (Compound 1-2ASS="ptx2">

So pl. 85-88oC.

1H-NMR (CDCl3-TMS) million D.: of 0.87 (t, J=7.2 Hz, 3H), of 1.18 (d, J=6.6 Hz, 6H), 1,57 was 1.69 (m, 2H), 3,09 (Sept., 1H), 3,88-of 3.94 (m, 2H), 4,74 (s, 2H), 5,0 (width, 1H), 6,80~to 7.18 (m, 4H).

Elemental analysis (C16H21ClN2OS):

Calculated (%): C 59,15 H 6,52 N 8,62 S 9,87 Cl 10,91

Found (%): C 58,92 H 6,51 N 8,67 S 9,89 Cl 10,79.

Example 30

Synthesis of [1-cyclopropylmethyl-5-(3,5-dichlorophenylthio)-4-isopropyl - 1H-imidazol-2-yl]methanol (Compound 1-30)

(1) 2-Benzoyloxymethyl-1-cyclopropylmethyl-5-(3,5-dichlorophenylthio)- 4-isopropyl-1H-imidazole (17T load) was obtained by the method described in example 17 synthesis (17g). Outputs connection (17T load) and its isomer provisions (17T load') was 86% and 10%, respectively.

(17T load') an oily substance,1H-NMR (CDCl3-TMS) million D.: 0,28-0,36 (m, 2H), 0.55 to 0.64 in (m, 2H), 0.99-of 1.16 (m, 1H), 1,35 (d, J=7.2 Hz, 6H), 3.04 from (Sept., 1H), 3,91 (d, J=6.6 Hz, 2H), of 4.54 (s, 2H) and 4.65 (s, 2H), 6,94 (d, J= 2.0 Hz, 2H),? 7.04 baby mortality (t, J= 2.0 Hz, 1H), 7,26 and 7.36 (m, 5H).

(17T load) an oily substance,1H-NMR (CDCl3- TMS) million D.: 0,18-0,26 (m, 2H), from 0.35 to 0.44 (m, 2H), 0,95-1,12 (m, 1H), 1,25 (d, J=7,0 Hz, 6H), to 3.09 (Sept., 1H), 3,82 (d, J=6.6 Hz, 2H), 4,55 (s, 2H), 4,70 (s, 2H), 6,78 (d, J= 2.0 Hz, 2H), to 7.09 (t, J=2.0 Hz, 1H), 7,27-7,40 (m, 5H).

Connection 1-30 was obtained from 2-benzoyloxymethyl-1-cyclopropylmethyl - 5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole (17T load), o-TMS) million doctor : of 0.29 and 0.37 (m, 2H), 0,41-of 0.53 (m, 2H), 1,00-1,20 (m, 1H), 1,17 (d, J=7,0 Hz, 6H), 3,05 (Sept., 1H), 3,88 (d, J=6.6 Hz, 2H), 4,79 (s, 2H), 5,52 (width, 1H), 6,79 (d, J=1.8 Hz, 2H), 7,10 (t, J= 1.8 Hz, 1H).

Elemental analysis (C17H20Cl2N2OS):

Calculated (%): C 54,99 H 5,43 N 7,54 8,64 S Cl KZT 19.09

Found (%): C 54,91 H 5,42 N 7,53 S 8,68 Cl 19,28.

Example 31

Synthesis of [1-benzoylmethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H - imidazol-2-yl]methanol (Compound 1-31)

(1) 1-Benzoylmethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p - methoxybenzyloxy)-1H-imidazole (17u) was obtained by the method described in example 16 synthesis (17f) (Yield 88%).

(17u) an oily substance,1H-NMR (CDCl3-TMS) million D.: 1,72 (d, J= 7.2 Hz, 6H), 3,14 (Sept., 1H), 3,74 (s, 3H), 4,36 (s, 2H), with 4.64 (s, 3H), 7,03 (t, J=0.9 Hz, 1H), to 7.09 (d, J=8,4 Hz, 2H), 7,46 (t, J=7.5 Hz, 2H), to 7.59 (t, J=7.5 Hz, 1H), 7,79 (DD, J=7.5 Hz, 0.9 Hz, 2H).

(2) Compound 1-31 was obtained from 1-benzoylmethyl-5-(3,5 - dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxy)-1H-imidazole (17u) by the method described in example 16 for the synthesis of Compounds 1-16. (75% yield). So pl. 205-211oC.

1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J=7,0 Hz, 6H), 3,13 (Sept., 1H), 4.72 in (s, 2H), 5,51 (s, 2H), 6,77 (d, J=2 Hz, 2H), 7,01 (t, J=1.8 Hz, 1H), 7,40-the 7.65 (m, 3H), 7,87 (dt, J=5.6 Hz, 1.4 Hz, 2H).

Example 32

Synthesis of [1-acetylethyl-5-(3,5-dichlorophenylthio)-4-ia, and then added 200 mg (1.2 mmol) of potassium iodide, and the mixture was stirred for 15 minutes at room temperature. Then added 437 mg (1.00 mmol) of 5-(3,5 - dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxy)-1H - imidazole (16b) and 170 mg (1.20 mmol) of potassium carbonate, after which the mixture is stirred for 5 hours and left overnight. This reaction mixture was concentrated under reduced pressure, and the residue was extracted with methylene chloride. The organic layer was washed with water, dried with anhydrous sodium sulfate, and the solvent was concentrated under reduced pressure. The residue was fractionally using chromatography on silica gel (ethyl acetate:methylene chloride = 1: 9). The oily substance was led from the ether and was obtained 270 mg (yield 62%) of 1-acetylethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p - methoxybenzyloxy)-1H-imidazole (17v).

So pl. 87-90oC.

1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J=6.8 Hz, 6H), of 1.97 (s, 3H), of 3.80 (s, 3H), of 4.38 (s, 2H), 4,60 (s, 2H), 4,74 (s, 2H), for 6.81 (d, J=2 Hz, 2H), at 6.84 (s, 1H), 6.89 in (t, J=1.8 Hz, 2H), 7,11 (t, J=2 Hz, 1H), 7,21 (d, J=8.6 Hz, 2H).

Elemental analysis (C24H26Cl2N2O3S):

Calculated (%): C 58,42 H 5,31 N 5,68 S 6,50 Cl 14,37

Found (%): C 58,23 H 5,32 N 5,81 S 6,55 Cl 14,69

(2) the Connection 1-Dong, described in example 16 for the synthesis of Compounds 1-16, (Yield 45%). So pl. 165-167oC.

1H-NMR (CDCl3-TMS) million D.: 1,21-of 1.27 (m, 6H), and 1.56 (s, 2H), 2,16 (s, 1H), 3,11 (Sept. , 1H), 3,55, 3,92 (sq, J= 12.9 Hz, 2H), 4,59 (C), 4,80, 4,96 (sq , J=15.6 Hz), 4,93 (C) 6,83 (t, J=1.8 Hz, 2H), 7,13 (t, J=1 Hz, 1H).

Elemental analysis (C16H18Cl2N2O2S 0,5 H2O):

Calculated (%): C 50,25 H 5,02 N 7,35 Cl a 18.57

Found (%): C 50,36 H 4,87 N 7,29 Cl 18,94.

Example 32

Synthesis of [1-(2-hydroxypropyl)-5-(3,5-dichlorophenylthio)-4-isopropyl - 1H-imidazol-2-yl]methanol (Compound 1-32')

In methanol (5 ml) was dissolved 371 mg (0.8 mmol) acetylethyl-2-benzoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole (17v), and then stirring at room temperature, was added 38 mg (1.0 mmol) of sodium borohydride, and the mixture was stirred for 1.5 hours. This reaction mixture was concentrated under reduced pressure and to the residue was added water and methylene chloride for extraction. The organic layer was washed with water and dried with sodium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel (ethyl acetate:methylene chloride = 1:9), resulting in a received 2-benzoyloxymethyl-5-(3,5 - dichlorophenylthio)-1-(2-guide the 1H-NMR (CDCl3-TMS) million D.: 1,14 (d, J=5.7 Hz, 3H), 1,25 (t, J=6.9 Hz), 2,72 (d, J= 4,8 Hz, 1H), 3,10 (Sept., 1H), 3,83-3,93 (m, 2H), br4.61 (DD, J= 15.6 Hz, 10,2 Hz, 2H), 4,71 (DD, J=42,3 Hz, 12 Hz, 2H), 6,38 (s, 2H), 7,11 (s, 1H), 7,26-7,37 (m, 5H).

Connection 1-32' was obtained from 2-benzoyloxymethyl-5-(3,5 - dichlorophenylthio)-1-(2-hydroxypropyl)-4-isopropyl-1H-imidazole (17v"') by the method described in example 17 for the synthesis of Compounds 1-17. (Yield 59%). So pl. 155-157oC.

1H-NMR (CDCl3-TMS) million D.: 1,21 (t, J=6.9 Hz) of 1.24 (d, J= 5.4 Hz, 3H), 3,09 (Sept. , 1H), 3.72 points Shir., 1H), 3,93 (Shir.C) of 3.97 (DD, J=34.8 Hz, 11.7 Hz, 2H), 4.72 in (DD, J=32,4 Hz and 13.5 Hz, 2H), 6,79 (width, 1H), 6,79 (d, J=1.8 Hz, 2H), 7,13 (t, J= 1,8 Hz).

Elemental analysis (C16H20Cl2N2O2S):

Calculated (%): C 51,20 lower than the 5.37 H N 7,46 Cl Rate 18.89 S 8,54

Found (%): C 51,25 H 5,32 N 7,38 Cl 18,82 S 8,56

Example 33

Synthesis of 2-[5-(3,5-dichlorophenylthio)-4-isopropyl-1-(1,1,1-triptorelin)- 1H-imidazol-2-yl]methanol (Compound 1-33)

(1) 5-(3,5-Dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxy)- 1-(1,1,1-triptorelin)-1H-imidazole (17w) was obtained by the method described in example 16 synthesis (17f). Outputs connection 17w and its isomer provisions 17w' was 58% and 6.4%, respectively.

17w': an oily substance,1H-NMR (CDCl3- TMS) million D.: of 1.33 (d, J=7 Hz, 6H), 2,90 (Sept., 1H), 3,80 (s, 3H), 4,48 (s, 2H), 4,69 society1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J=7.2 Hz, 6H), 3,10 (Sept., 1H), 3,81 (s, 3H), 4,47 (s, 2H), 4,69 (sq, J=17 Hz, 2H), 4,74 (s, 2H), 6,77 (d, J=1.8 Hz, 2H), to 6.88 (d, J=8.7 Hz, 2H), 7,12 (s, 1H), 7.23 percent (d, J=8.7 Hz, 2H).

Connection 1-33 was obtained from 5-(3,5-dichlorophenylthio)-4-isopropyl - 2-(p-methoxybenzyloxy)-1-(1,1,1-triptorelin)-1H-imidazole (17w) by the method described in example 16 for the synthesis of Compounds 1-16. (Yield 82%). So pl. 134-136oC.

1H-NMR (CDCl3-TMS) million D.: 1,22 (d, J=6.9 Hz, 6H), 3,06 (Sept., 1H), 3,30-to 3.38 (m, 1H), 4.72 in (sq, J=8,4 Hz, 2H), 4,84 (d, J=6 Hz, 2H), 6,79 (d, J=1.8 Hz, 2H), 7,14 (d, J= 2 Hz, 1H).

Elemental analysis (C15H15Cl2F3N2S)

Calculated (%): C 45,12 H 3,79 N 7,02 Cl 17,76 F 14,27 S 8,03

Found (%): C 45,30 H 3,85 N 7,00 Cl 17,98 F 14,26 S 7,95.

Example 34

Synthesis of [1-vermeil-5-(3,5-dichlorophenylthio)-4-isopropyl-1H - imidazol-2-yl]methanol (Compound 1-34)

In dimethyl sulfoxide (20 ml) was dissolved 814 mg (2.0 mmol) of 2-benzoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropylimidazole (16A), cooling up to 0-3oC, and then, stirring was added 1.44 g (10.4 mmol) of potassium carbonate, and the mixture was stirred at this temperature for 15 minutes. Then was added 270 mg (2,40 mmol) brumptomyia, and the resulting mixture stirred for 30 minutes at the same temperature, and is Oh, were extracted with ethyl acetate, and the organic layer was washed with water and dried with sodium sulfate. The solvent was concentrated under reduced pressure, and the crude product was fractionally using chromatography on silica gel (ethyl acetate:methylene chloride = 1:19). From the first fraction was obtained 137 mg (yield 16%) of isomer provisions (17x') of target compound in the form of an oily product. And from the subsequent fractions were obtained 700 mg of 2-benzoyloxymethyl-5-(3,5 - dichlorophenylthio)-1-vermeil-4-isopropyl-1H-imidazole (17x) of target compound in the form of an oily product (yield 80%).

17x': an oily substance,1H-NMR (CDCl3- TMS) million D.: of 1.35 (d, J= 6.9 Hz, 6H), 3,23 (Sept., 1H), 4,56 (s, 2H), to 4.73 (s, 2H), 6,04 (d, J=52,2 Hz, 2H), 6,97 (d, J=1.5 Hz, 2H), to 7.09 (d, J=1.5 Hz, 1H), 7.3 to 7.4 (m, 5H).

17x: an oily substance,1H-NMR (CDCl3- TMS) million D.: of 1.26 (d, J= 7.2 Hz, 6H), 3,12 (Sept., 1H), 4,57 (s, 2H), 4,78 (s, 2H), of 5.99 (d, J=52,2 Hz, 2H), 6,85 (d, J=1.8 Hz, 2H), 7,13 (d, J=1.8 Hz, 1H), 7,30-7,76 (m, 5H).

Connection 1-34 was obtained from 2-benzoyloxymethyl-5-(3,5 - dichlorophenylthio)-1-vermeil-4-isopropyl-1H-imidazole (17x) by the method described in example 17 for the synthesis of Compounds 1-17. (Yield 86%). So pl. 115-117oC.

1H-NMR (CDCl3-TMS) million D.: 1,21 (d, J=7.2 Hz, 6H), 3,12 (Sept., 1H), 3,98 (t, J= 6.3 Hz, 1H), a 4.86 (d, J=6.3 Hz, 2H), 6,04 ):

Calculated (%): C 48,15 H 4,33 N 8,02 Cl 20,30 F 5,33 S 9,18

Found (%): C 48,01 H 4,36 Of 7.96 N Cl 20,36 F 5,63 S 9,25.

Example 35

Synthesis of [5-(3,5-dichlorophenylthio)-1-(1-foradil)-4-isopropyl-1H - imidazol-2-yl]methanol (Compound 1-35)

2-Benzoyloxymethyl-5-(3,5-dichlorophenylthio)-1-foradil-4-isopropyl - 1H-imidazole (17y) was obtained by the method described in example 17 synthesis of Compound 17f. Outputs connection (17y) and its isomer provisions (17y') was 95% and 4%, respectively.

17y': an oily substance,1H-NMR (CDCl3- TMS) million D.: of 1.33 (d, J=7 Hz, 6H), to 3.02 (Sept., 1H), 4,27 (t, J= 3 Hz, 1H), to 4.38 (t, J=4,8 Hz, 1H), 4,50 (t, J=4,8 Hz,1H), 4,74 (t, J= 5.4 Hz, 1H).

17y: an oily substance,1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J=7 Hz, 6H), 3,10 (Sept., 1H), 4,25 (d, J=4,8 Hz, 1H), 4,20-4,56 (m, 2H), 4,56 (s, 2H), 4,56~4,60 (m, 2H), to 4.73 (s, 2H), 6,80 (d, J=3 Hz, 2H), 7,11 (t, J=3 Hz, 1H), 7,29-to 7.35 (m, 5H).

Connection 1-35 was obtained from 2-benzoyloxymethyl-5-(3,5 - dichlorophenylthio)-1-foradil-4-isopropyl-1H-imidazole (17y) by the method described in example 17 for the synthesis of Compounds 1-17. (Yield 58%). So pl. 131-132oC.

1H-NMR (CDCl3-TMS) million D.: of 1.23 (d, J=5.6 Hz, 6H), to 3.09 (Sept., 1H), 4,0 (t, J=7.5 Hz, 1H), 4,29 (t, J=5.4 Hz, 1H), 4,37 (t, J=5.4 Hz, 1H), to 4.52 (t, J=5,1 Hz, 1H), br4.61 (t, J= 5,1 Hz, 1H), 6,80 (d, J=2.1 Hz, 2H), 7,13 (t, J=2.1 Hz, 1H).

Elemental analysis (C15H8,86.

Example 36

Synthesis of [5-(3,5-differenlty)-1-ethyl-4-isopropyl-1H-imidazol - 2-yl]methanol (Compound 1-36).

In dimethylformamide (10 ml) was dissolved 432 mg (1.2 mmol) 2-benzoyloxymethyl-5-(3,5-differenlty)-4-isopropyl-1H-imidazole (16f), and then stirring at room temperature, was added 192 mg (1.4 mmol) of potassium carbonate and 153 mg (1.4 mmol) of brometane, and the resulting mixture stirred at this temperature for 3 days. The reaction mixture was extracted with ether, and the ether layer washed with water, dried with magnesium sulfate and filtered. The ether layer was concentrated under reduced pressure, and the oily residue was purified by chromatography on silica gel (methanol:methylene chloride = 3: 97). From the first fraction received 20 mg (yield of 4.3%) of isomer provisions (17z') of the target compound. From the subsequent fraction received 300 mg of 2-benzoyloxymethyl-5-(3,5-differenlty)-1-ethyl-4-isopropyl - 1H-imidazole (17z), which was used in the next reaction.

(Yield 65%). An oily substance.

17z': an oily substance, 1H-NMR (CDCl3-TMS) million days of 1.34 (d, J= 6,9, 6H), of 1.35 (t, J=7.0 Hz, 3H), 3.00 and-3,10 (m, 1H), 4,05 (sq, J=7,0 Hz, 2H), 4,55 (s, 2H) and 4.65 (s, 2H), 6,46-of 6.65 (m, 3H), 7,25-7,40 (m, 5H);

17z oily substance,1H-NMR (CDCl3- TMS) million is 2">

1H-NMR (CDCl3) 3a of 1.34 (d, J=6.9 Hz, 6H), of 1.35 (t, J=7.0 Hz, 3H), 3.00 and-3,10 (m, 1H), 4,05 (sq, J=7,0 Hz, 2H), 4,55 (s, 2H) and 4.65 (s, 2H), 6,46-of 6.65 (m, 3H), 7,25-7,40 (m, 5H).

In 5 ml of ethanol was dissolved 300 mg (0.75 mmol) of 2-benzoyloxymethyl - 5-(3,5-differenlty)-1-ethyl-4-isopropyl-1H-imidazole (17z), and then stirring at room temperature, was added 5 N HCl (10 ml) and the resulting mixture was left for reaction in an oil bath at 130oC for three hours, during which time the mixture was concentrated. After the reaction mixture was extracted with ethyl acetate, an ethyl acetate layer was washed with water and dried with magnesium sulfate, and the solvent is kept at reduced pressure. The oily residue was led from n-hexane and filtered, resulting in a received 160 mg of Compound 1-36 (yield 68%). So pl. 102-104oC.

1H-NMR (CDCl3-TMS) million D.: 1,19 (d, J= 6.8 Hz, 6H), 1,25 (t, J=7.2 Hz, 3H), is 3.08 (Sept.), as 4.02 (sq, J= 7.2 Hz, 2H), of 4.44-4,60 (width, 1H), 4,70-4,80 (width, 2H), 6,46-only 6.64 (m, 3H).

Example 37

Synthesis of [1-ethyl-5-(3-forfinally)-4-isopropyl-1H-imidazol - 2-yl]methanol (Compound 1-37)

2-Benzoyloxymethyl-1-ethyl-5-(3-forfinally)-4-isopropyl-1H - imidazole (17aa) was obtained by the method described in example 36 synthesis of compounds 17z. Outputs connection (17aa) and its isomer provisions (17aa') 34 (d, J= 7,4 Hz, 6H), of 1.35 (t, J=7.4 Hz, 3H), 3,06 (Sept., 1H), 4,05 (sq, J=7,4 Hz, 2H), 4,55 (s, 2H) and 4.65 (s, 2H), 6,70-of 6.90 (m, 3H), 7,08-7,20 (m, 1H), 7,25-7,40 (width, 5H).

17aa oily substance1H-NMR (CDCl3-TMS) million D.: 1,17 (d, J=7.2 Hz, 6H), 1,25 (t, J=7.0 Hz, 3H), 3,13 (Sept., 1H), 3,97 (sq, J=7.2 Hz, 2H), 4,56 (s, 2H), 4,67 (s, 2H), 6,60-6,86 (m, 3H), 7,13-7,24 (m, 1H), 7,28-7,38 (width, 5H).

Connection 1-37 was obtained from 2-benzoyloxymethyl-1-ethyl-5-(3 - forfinally)-4-isopropyl-1H-imidazole (a) was obtained by the method described in example 36 synthesis of compounds 1-36. (Yield 61%). So pl. 88-90oC.

1H-NMR (CDCl3-TMS) million D.: of 1.18 (d, J=7,0 Hz, 6H), of 1.23 (t, J=7.4 Hz, 3H), 3,11 (Sept., 1H), 4.04 the (sq, J=7,4 Hz, 2H), 4,70-5,30 (width, 1H), and 4.75 (s, 2H), 6,61~6,85 (m, 3H), 7,13-7,24 (m, 1H).

Example 38

Synthesis of [4-(3-chlorophenylthio)-5-isopropyl-1-methyl-1H-imidazol-2 - yl]methanol (Compound 1-38)

In 218 g of anhydrous dimethylformamide was dissolved 21.8 g (58,5 mmol) 2-benzoyloxymethyl-5-(3-chlorophenylthio)-4-isopropyl-1H-imidazole (e), and then was added 12.2 g (88,3 mmol) of anhydrous potassium carbonate and 11.6 g (81,7 mmol) methyliodide, and the mixture is stirred at room temperature for 7 hours. To the reaction mixture were added ice water and the mixture was extracted with diethyl ether. The extract was washed with water and dried with sodium sulfate. The solvent was concentrated the 1:8). From the first elyuirovaniya faction received 620 mg (yield 3%) 2-benzoyloxymethyl-4-(3-chlorophenylthio)-5-isopropyl-1-methyl-1H - imidazole (17ab') in the form of an oily product. From the last elyuirovaniya fractions were obtained by 17.6 g (yield 78%) of 2-benzoyloxymethyl - 5-(3-chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole (17ab) as an oily product.

17ab':1H-NMR (CDCl3-TMS) million D.: of 1.30 (d, J= 7.2 Hz, 6H), 3,20 (Sept. , 1H), the 3.65 (s, 3H), 4,55 (s, 2H) and 4.65 (s, 2H), of 6.96-7,34 (m, 9H).

17ab:1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J= 7,0 Hz, 6H), 3.15 in (Sept., 1H), 3,51 (s, 3H), of 4.54 (s, 2H); and 4.68 (s, 2H), 6,78-7,35 (m, 9H).

5.8 ml of concentrated hydrochloric acid was dissolved 580 mg (1.5 mmol) 2-benzoyloxymethyl-4-(3-chlorophenylthio)-5-isopropyl-1-methyl - 1H-imidazole (17ab'), and the resulting mixture was heated under reflux at 110oC for 6 hours. Then the reaction mixture was neutralized with saturated aqueous sodium bicarbonate solution and was extracted with methylene chloride. The organic layer was washed with water and dried with sodium sulfate, and the solvent is kept at reduced pressure. The crude product is recrystallized from a mixture of ethyl acetate and isopropyl ether, resulting in the received 289 mg of target Compound 1-38 (yield 65%). So pl. 105-106oC.

<>IR (Nujol") 3146 cm-1< / BR>
Elemental analysis (C14H17ClN2OS):

Calculated (%): C 56,65 H 5,77 N 9,44 S 10,80 Cl 11,94

Found (%): C 56,75 H 5,77 N 9,39 S 10,80 Cl 11,93

Example 39

Synthesis of [4-(3,5-dichlorophenylthio)-5-isopropyl-1-methyl-1H-imidazol - 2-yl]methanol (Compound 1-39)

Connection 1-39 was obtained from the compound (17b') by the method described in Comparative example 2 for the synthesis of Compounds 1-8. So pl. 167-168oC.

1H-NMR (CDCl3-TMS) million D.: 1,31 (d, J=7.2 Hz, 6H), 3,20 (Sept., 1H), 3,69 (s, 1H), with 4.64 (s, 2H), 6,91 (d, J= 1.8 Hz, 2H), 7,05 (t, J=1.8 Hz, 1H).

Elemental analysis (C14H16Cl2N2OS):

Calculated (%): C 50,76 H 4,87 N 8,46 S 9,68 Cl 21,40

Found (%): C 50,73 H 4,86 Charged 8.52 N S 9,76 Cl 21,35.

Comparative example 3

Synthesis of 2-benzoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl - 1-methyl-1H-imidazole (17A).

In 50 ml of methylene chloride was added 15.0 g (35.8 mmol) of hydrochloric acid ethyl ester of glycine, and then added 9.2 grams (75,3 mmol) of 4-dimethylaminopyridine, cooling, while the ice. After 10 minutes of stirring, drop by drop for 30 minutes was added to 6.5 ml (39,4 mmol) benzyloxyacetaldehyde, cooling with ice. Then the temperature was raised to room temperature, and the mixture was stirred for 12 hours. Kyu mixture was extracted with methylene chloride. The extract was washed with saturated saline, dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated and obtained 9.0 g of ethyl ether complex N-benzyloxycarbonylglycine (yield 100%).

1H-NMR (CDCl3-TMS) million D.: of 1.29 (t, J=7.0 Hz, 3H), a 4.03 (s, 2H), 4,07 (d, J=5.4 Hz, 2H), 4,23 (sq, J=7,0 Hz, 2H), br4.61 (s, 2H), 7,09 (width, 1H), was 7.36 (s, 5H).

Elemental analysis (C13H17NO4):

Calculated (%): C 62,14 H 6,82 N 5,57

Found (%): C 62,10 H 6,80 N 5,51.

In 10 ml of anhydrous tetrahydrofuran was dissolved 21,0 g (4.0 mmol) of ethyl ester of N-benzyloxycarbonylglycine, and then added 175,0 mg (4.4 mmol) of sodium hydride (60% oil suspension) under cooling with ice. After 10 minutes of stirring, drop by drop for 30 minutes was added 473,0 μl (7.6 mmol) under the conditions, cooling with ice. Then the temperature was raised to room temperature, and the mixture is stirred for 12 hours. To this mixture was added 10 ml of tetrahydrofuran and filtered. To the filtrate was added 5% hydrochloric acid and was extracted with ethyl acetate. The extract was washed with saturated saline solution, dried with anhydrous sodium sulfate and filtered. The obtained filtrate was concentrated. The crude product was purified by chromatography on Silmarillion (18) (output 40,7%).

1H-NMR (CDCl3-TMS) million D.: 1,20; 1,28 (t 2, J=7,0 Hz, 3H), 3,01, 3,07 (2, 3H), 4,13, 4,16 (2, 2H), 4,08, 4,20 (square 2, J=7,0 Hz, 2H), 4,16, 4,25 (2, 2H), 4,54, with 4.64 (2, 2H), 7,27-7,40 (m 2, 5H).

Elemental analysis (C14H19NO40,1 H2O)

Calculated (%): C 62,95 H 7,25 N 5,24

Found (%): C 63,01 H 7,24 N 5,25.

In 4 ml of anhydrous tetrahydrofuran was dissolved 272,6 μl (1.9 mmol) of Diisopropylamine, and then for 10 minutes at 0oC was added 1.0 ml (1.7 mmol) of n-utility (1.7 M solution of hexane). After 30 minutes stirring at 0oC, the mixture was cooled in a bath of dry ice to -78oC for 10 minutes was added 430,0 mg (1.6 mmol) of ethyl ester of N-benzyloxyethyl-N-methylglycine. After stirring at -78oC for 1 hour, the mixture was heated to -40oC, and then cooled to -78oC. then, within 10 minutes, one drop was added tertrahydrofuran ring solution (2.0 ml) 635,1 mg (1.8 mmol) of 3,5-dichlorobenzaldehyde. After 30 minutes of stirring the temperature was raised to room temperature and was added 5% hydrochloric acid. The mixture was extracted with ethyl acetate. The extract was washed with saturated saline solution, dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The crude product was purified with peacetul - N-methyl)amino-2-(3,5-dichlorophenylthio)acetate (19) (yield of 13.6%).

1H-NMR (CDCl3-TMS) million D.: is 1.31 (t, J=7.0 Hz, 3H), 3.04 from (s, 3H), 4,13 (d, J=2.4 Hz, 2H), 4.26 deaths (sq, J=7,0 Hz, 2H), 4,49 (sq, J=7.8 Hz, 2H), 6.90 to (s, 1H), 7,21-7,40 (m, 8H).

In 10 ml of ethanol was dissolved 890,0 mg (2.0 mmol) of ethyl 2-(N-benzyloxyethyl-N-methyl)amino-2-(3,5-dichlorophenylthio)-acetate (19), and then added of 124.7 mg (2.1 mmol) of 86% potassium hydroxide while cooling with ice. The temperature was raised to room temperature, after which the mixture is stirred for 1 hour, and precipitated crystals were filtered. To the crystals was added 5% hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with saturated saline solution, dried with anhydrous sodium sulfate, filtered and concentrated, resulting in a received 640,0 mg of 2-(N-benzyloxyethyl-N-methyl)amino-2-(3,5-dichlorophenylthio) acetic acid (yield 78.5 per cent).

1H-NMR (CDCl3-TMS) million D.: 3,05 (s, 3H), 4,14 (d, J=2.0 Hz, 2H), 4,48 (d, J=5.4 Hz, 2H), 6,85 (s, 1H), 7,00 (width, 1H), 7,25-7,40 (m, 8H).

In 5 ml of anhydrous toluene was dissolved 500.0 mg (1.2 mmol) of 2-(N-benzyloxyethyl-N-methyl)amino-2(3,5-dichlorophenylthio)acetic acid, after which, at room temperature, was added 210,6 μl (2.4 mmol) of oxalicacid, and the resulting mixture was stirred for 1 hour. Toluene drove under reduced davlenie, added 2.4 ml (4.8 mmol) of the chloride Isopropylamine (2.0 M solution of tetrahydrofuran). After that, the mixture was heated to 0oC and again cooled to -78oC and then added to the above tertrahydrofuran ring solution (5 ml) of the acid chloride. The resulting mixture was stirred for 30 minutes and was added 10 ml of methanol at -78oC, after which the temperature was raised to room temperature. Then added 3 ml of water and 5 ml of diethyl ether, and the mixture was filtered through celite. The filtrate was extracted with diethyl ether. The extract was washed with saturated saline solution, dried with anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by chromatography on silica gel (ethyl acetate: hexane = 1:5), which was obtained 2-benzyloxy-N-[1-(3,5-dichlorophenylthio)-3-methyl-2-oxobutyl]-N - methylacetamide (20).

1H-NMR (CDCl3-TMS) million D.: 1,15 (d, J = 3.8 Hz, 3H), of 1.18 (d, J=4.0 Hz, 3H), to 3.02 (s, 3H), 4,15 (d, J= 3,4 Hz, 2H), 4,51 (d, J=6.0 Hz, 2H), 7,02 (s, 1H), 7,22-7,40 (m, 8H).

In acetic acid was dissolved 2-benzyloxy-N-[1-(3,5 - dichlorophenylthio)-3-methyl-2-oxobutyl] -N-methylacetamide (20), and then was added ammonium acetate and the resulting mixture was heated under reflux. After 1 hour the reaction mixture was concentrated privale saturated salt solution, was dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated and obtained 2-benzyloxy-5-(3,5-dichlorophenylthio)-4-isopropyl-1H - Mei (17A).

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J= 7,0 Hz, 6H), 3,51 (s, 3H), of 4.54 (s, 2H), 4,69 (s, 2H), 6,79 (s, 2H), 7,10 (s, 1H), 7,22-7,40 (m, 5H).

Comparative example 4

Synthesis of 2-benzyloxy-N-[1-(3,5-dichlorophenylthio)-3-methyl-2 - oxobutyl]-N-methylacetamide (20)

To 300 ml of anhydrous methanol was added to 43.1 mg (0.5 mol) of 3-methyl-2-butanone, and the resulting mixture was stirred at 5oC. and Then for 30 minutes at 10oC was added to 27.3 ml (0.5 mol) of bromine. After 1 hour stirring at 10oC was added 150 ml of water, and then the temperature of the mixture was brought to room temperature, and the mixture is stirred for 3 hours. After adding 300 ml of water the mixture 3 times was extracted with 500 milliliters of diethyl ether. The extract was washed with saturated aqueous sodium bicarbonate solution and then saturated saline, and then to diethylamino layer was added calcium chloride. The resulting mixture was stirred for 1 hour to dehydration. Then diethylamine layer was filtered, concentrated at a temperature below 30oC, and the condensate is kept under reduced pressure, result (CDCl3-TMS) million D.: of 1.18 (d, J=6.0 Hz, 6H), 2,99 (m, 1H), 4.00 points (s, 2H).

To a stirred mixture 42,4 ml of 25% aqueous solution of methylamine and 24.2 ml of tetrahydrofuran for 30 minutes at 10oC was added 10.0 g (to 60.6 mmol) 1-bromo-3-methyl-2-butanone. The mixture is stirred for 30 minutes at 10oC and then added to 18.0 ml of diethyl ether and 12.1 g of potassium carbonate, and the mixture was stirred for 10 minutes at room temperature. Diethyl layer was separated, washed with saturated salt solution, dried with anhydrous potassium carbonate and filtered. The filtrate was concentrated and received 6,09 g 3-methyl-1-methylamino-2-butanone (yield 87%).

A mixture of 6.1 g (52,9 mmol) 3-methyl-1-methylamino-2-butanone, 70,0 ml ethyl acetate and was 41.0 ml of water is stirred at 0oC. was Then added to 7.1 g (to 84.6 mmol) of sodium bicarbonate, and the mixture is stirred for 10 minutes. After that for 30 minutes was added to 8.5 ml (54,0 mmol) benzyloxyacetaldehyde. The mixture is stirred for 10 hours at room temperature, and then an ethyl acetate layer was separated, washed with saturated salt solution, dried with anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by chromatography on silica gel (hexane:ethyl acetate = 1:1), CDCl3-TMS) million D.: the 1.04 and 1.15 (d 2, J=6,6 Hz, 6H), 2,94, 3,01 (2, 3H), 2,52, 2,66 (m 2, 1H), 4,06, 4,25 (2, 2H), 4.25 in, 4,30 (2, 2H), 4,49, with 4.64 (2, 2H), 7,27 was 7.45 (m, 5H).

In 2 ml of anhydrous tetrahydrofuran was dissolved 100 mg (0.4 mmol) 2-benzyloxy-N-methyl-N-(3-methyl-2-oxobutyl)-ndimethylacetamide (18a'), and then stirring at -78oC for 10 minutes was added 223 μl (0.4 mmol) of n-utility (1.7 M solution of hexane). The mixture is stirred for 1 hour at -78oC, after which this mixture for 10 minutes was added tertrahydrofuran ring solution (1 ml) 135 mg (0.4 mmol) of 3,5-dichlorophenylthio. After 30 minutes the temperature was raised to room and added a saturated aqueous solution of ammonium chloride, after which the mixture was extracted with ethyl ester of acetic acid. The extract was washed with saturated saline, dried with anhydrous sodium sulfate, filtered and concentrated. The crude product was purified by chromatography on silica gel (hexane:ethyl acetate = 5:1), resulting in a received 79 mg of 2-benzyloxy-N-[1-(3,5 - dichlorophenylthio)-3-methyl-2-oxobutyl]-N-methylacetamide (20) (yield 47%).

1H-NMR (CDCl3-TMS) million D.: 1,15 (d, J=3.8 Hz, 3H), of 1.18 (d, J=4.0 Hz, 3H), to 3.02 (s, 3H), 4,15 (d, J=3,4 Hz, 2H), 4,51 (d, J=6.0 Hz, 2H), 7,02 (s, 1H), 7,22-7,40 (m, 8H).

Comparative example 5

Synthesis of 2-benzilic obom, described in Comparative example 4 synthesis of compound (18a').

1H-NMR (CDCl3-TMS) million D.: 1,12 (d, J=7,4 Hz, 6H), of 1.12 (t, J=7.2 Hz, 3H), 2,61 (sq, J=7.2 Hz, 2H), only 3.57 (s, 2H), only 3.57 (m, 1H, in), 3.75 (m, 1H).

2-Benzyloxy-N-ethyl-N-(3-methyl-2-oxobutyl)-ndimethylacetamide (18b') was obtained by a method described in Comparative example 4 synthesis of 2-benzyloxy-N-methyl-N-(3-methyl-2-oxobutyl)-ndimethylacetamide.

1H-NMR (CDCl3-TMS) million D.: 1,05, of 1.16 (d 2, J=7.2 Hz, 6H), to 1.11 to 1.15 (t, 2, J=7.5 Hz, 3H); 2,55, 2,71 (m 2, 1H), 3,37 (square 2, J=7.5 Hz, 2H), was 4.02, 4,19 (2, 2H), 4.25 in, 4,28 (C2, 2H), 4,49, with 4.64 (c2, 2H), 7,27-7,41 (m, 5H).

2-benzyloxy-N-[1-(3,5-dichlorophenylthio)-3-methyl-2-oxobutyl]- N-ethylacetamide (20b) was obtained by a method described in Comparative example 4 synthesis of compound (20).

1H-NMR (CDCl3-TMS) million D.: 1,09 (t, J=7.4 Hz, 3H) and 1.15 (d, J=7,0 Hz, 3H), 1,20 (d, J=7,0 Hz, 3H), 2,99 (m, 1H), 3,35 (m, 1H), 3,60 (m, 1H), 4,19 (d, J=6.6 Hz, 2H), 4,57 (d, J=9.4 Hz, 2H), PC 6.82 (s, 1H), 7,24 (s, 1H), 7,27 (s, 2H), 7,34 (s, 5H).

2-Benzoyloxymethyl-5-(3,5-dichlorophenylthio)-1-ethyl-4-isopropylimidazole (17o') was obtained by a method described in Comparative example 3 synthesis of compound (17a).

1H-NMR (CDCl3-TMO) million D.: of 1.18 (t, J=7.0 Hz, 3H), 1,25 (d, J=7,0 Hz, 3H), 3,10 (m, 1H), 3,97 (sq, J=7,4 Hz, 2H), 4,56 (s, 2H), and 4.68 (s, 2H), 6,80 (s, 2H), 7,10 (s, 1H), 7,26 - 7,40 (m, 5H).

Example 40

the methylene chloride (10 ml) was dissolved 220 mg (0,700 mmol) [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl] methanol (Compound 1-8), and then added 201 mg (2.00 mmol) of triethylamine. To the resulting mixture under ice cooling was added 78,0 mg (1.00 mmol) of acetylchloride, and the mixture is stirred for 30 minutes at the same temperature. Then for neutralization was added saturated aqueous sodium bicarbonate solution, and the resulting mixture was extracted with methylene chloride. The organic layer was washed with water and dried with sodium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel (ethyl acetate: n-hexane = 1: 1), which was obtained 170 mg of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol - 2-yl]acetate (Compound 1-40) (yield 69%). So pl. 92-93oC.

1H-NMR (CDCl3-TMS) million D.; of 1.26 (d, J=6.8 Hz, 6H), 2,12 (s, 3H), 3,13 (Sept., 1H), 3,54 (s, 3H), to 5.21 (s, 2H), to 6.80 (m, 2H).

Example 41

Synthesis of 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl - 1-methyl-1H-imidazole (Compound 1-41).

In anhydrous tetrahydrofuran (72 ml) was dissolved 23,9 g (72.2 mmol) [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2 - yl] methanol (Compound 1-8), and the resulting mixture was cooled to (-40) - (-30)oC. To this mixture, stirring, was added drop of 16.3 r (86,6 mmol) trichloroacetimidate. When you are finished adding R the reaction mixture was added ice and stirred at room temperature. The solvent is kept under reduced pressure, and the residue was extracted with methylene chloride. The organic layer was washed saturated aqueous sodium bicarbonate, then with brine and was dried with magnesium sulfate. The solvent was concentrated under reduced pressure. Oily residue of 2-(N-trichloroethanol)oxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole was dissolved in methanol (200 ml), then was added 20 ml of triethylamine and 20 ml of water, and the mixture was heated under reflux for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was extracted with methylene chloride. The organic layer is washed with aqueous saturated sodium bicarbonate solution and then with brine and was dried with magnesium sulfate. The solvent was concentrated under reduced pressure, and the residue was led from 100 ml of diethyl ether. After filtering received an increase of 22.7 g of 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-4 - isopropyl-1-methyl-1H-imidazole (Compound 1-41) (yield 87%).

So pl. 146-148oC

1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J=7,0 Hz, 6H), 3,13 (Sept., 1H), of 3.56 (s, 3H), 4.75 in (lat., 2H), 5,23 (s, 2H), 6,80 (d, J=1.6 Hz, 2H), 7,13 (t, J=1.6 Hz, 1H).

Elemental analysis (C15H17

Example 42

Synthesis of 2-carbamoyloxymethyl-5-(3-chlorophenylthio)-4-isopropyl - 1-methyl-1H-imidazole (Compound 1-42)

Connection 1-42 was obtained from Compound 1-13 method described in example 41 synthesis of Compounds 1-41 by obtaining an intermediate compound 2-(N-trichloroethanol)oxymethyl-5- (3-chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole.

Measured the NMR spectrum of the intermediate compounds.

1H-NMR (CDCl3-TMS) million D.: of 1.27 (d, J=7,0 Hz, 6H), 3,19 (Sept., 1H), 3,63 (s, 3H), of 5.40 (s, 2H), at 6.84 (dt, J= 7,4 Hz, 2.0 Hz, 1H), 6,93 (t, J=2.0 Hz, 1H), 7,10-of 7.23 (m, 2H).

Connection 1-42, so pl. 117~118oC

1H-NMR (CDCl3-TMS) mn d: 1,26 (d, J=7,0 Hz, 6H), and 3.16 (Sept., 1H), of 3.56 (s, 3H), 4,80 (VIR., 2H), with 5.22 (s, 2H), 6,79-6,83 (m, 1H), 6,93-6,94 (m, 1H), 7,09-7,19 (m, 2H).

Example 43

Synthesis of 5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl - 2-(N-methylcarbamoyl)oxymethyl-1H-imidazole (Compound 1-43).

In anhydrous tetrahydrofuran (6 ml) was dissolved 0,300 g (of 0.91 mmol) [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2 - yl] methanol (Compound 1-8) and of 0.48 ml (8,15 mmol) of methyl isocyanate. To this solution was added 0.04 ml of bis(tributylamine)oxide, and the resulting mixture was stirred at room temperature for 2.5 hours. The reaction mixture was concentrared = 1:4) and recrystallized from isopropyl ether, resulting received 0,345 g of Compound 1-43 (yield 98%).

So pl. 112-113oC.

1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J=7,0 Hz, 6H), 2,82 (d, J=4,8 Hz, 3H), 3,13 (Sept., 1H), of 3.56 (s, 3H), 4,78 (width, 1H), 5,22 (s, 2H), 6,79 (d, J=2.0 Hz, 2H), 7,12 (t, 2.0 Hz, 1H).

Elemental analysis (C16H19Cl2N3O2S)

Calculated (%): C 49,49 H 4,93 N 10,82 S compared to 8.26 Cl 18,26

Found (%): C 49,47 H 4,94 N 10,87 S 8,20 Cl 18,35.

Example 44

Synthesis of 5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-2-(N - methylthiocarbamate)oxymethyl-1H-imidazole (Compound 1-44)

To an anhydrous solution of tetrahydrofuran and dimethylformamide (1:1 volume/volume, 1 ml) containing 50 mg (0.15 mmol) [5-(3,5 - dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl] methanol (Compound 1-8), was added 6.6 mg (0,17 mmol) of 60% sodium hydride in a nitrogen atmosphere, and the mixture was stirred for 30 minutes at room temperature. Then, with ice cooling was added 22 mg (0.3 mmol) of methyl isocyanate. The resulting mixture was stirred at the same temperature for 30 minutes and then another 30 minutes at room temperature. To the reaction mixture to complete the reaction was added an aqueous solution of ammonium chloride. Then the mixture was extracted with diethyl ether. The organic layer was washed the feast upon the residue was purified by chromatography on silica gel (ethyl acetate:n-hexane = 1: 1), as a result, we obtained 37 mg of 5-(3,5-dichlorophenylthio)-4 - isopropyl-1-methyl-2-(N-methylthiocarbamate)oxymethyl-1H-imidazole (Compound 1-44) (yield 60%). So pl. 119-121oC.

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J= 6.8 Hz, 6H), 3,11 (d, J=4,8 Hz, 3H), 3,12 (Sept., 1H), 3,55 (s, 3H), 5,59 (s, 2H), 6,70 (width, 1H), 6,80 (d, J=1.8 Hz, 2H), 7,13 (t, J=1.8 Hz, 1H).

Elemental analysis (C16H19Cl2N3OS2)

Calculated (%): C 47,52 H 4,74 accounted for 10.39 N S 15,86 Cl 17,53

Found (%): C 47,27 H 4,80 N 10,33 S 15,73 Cl 17,84.

Example 45

Synthesis of 1-benzyl-2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)- 4-isopropyl-1H-imidazole (Compound 1-45)

In anhydrous tetrahydrofuran was dissolved 204 mg (0.50 mmol) [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2 - yl]methanol (Compound 1-8) and to the resulting solution, stirring at room temperature, one drop was added 72 mg (0,60 mmol) characaterization. After the mixture is stirred at this temperature for 1 hour. The reaction mixture was neutralized with saturated aqueous sodium bicarbonate solution and was extracted with ethyl acetate. The organic layer was washed with water, and dried with sodium sulfate. The solvent was concentrated under reduced pressure, and the thus obtained oily 1-benzyl-2-(N-chlorine cleaning.

1H-NMR (CDCl3-TMS) million D.: of 1.30 (d, J=6.9 Hz, 6H), and 3.16 (Sept., 1H), 4,32 (s, 2H, in), 5.25 (s, 2H), 5,27 (s, 2H), of 6.71 (d, J=3 Hz, 2H), 6,85-6,87 (m, 2H),? 7.04 baby mortality (d, J=1.8 Hz, 1H), 7,2-7,3 (m, 3H), 7,65 (W, 1H).

The above intermediate compound was dissolved in methanol (3 ml), and then stirring at room temperature, was added 0.1 ml of water and 5 mg of zinc dust. The resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and to the residue to neutralize added a saturated aqueous solution of sodium bicarbonate. Nerastvorim material was filtered through celite, and the filtrate was extracted with methylene chloride. The extract was washed with water, dried with sodium sulfate and concentrated under reduced pressure. The residue was led from diethyl ether and filtered, resulting in a received 115 mg of the Compound 1-45 (51% yield from (12A)). So pl. 60-65oC (decomposition with evolution of gas).

1H-NMR (CDCl3-TMS) million D.; of 1.29 (d, J=7.2 Hz, 6H), 3.15 in (Sept., 1H), 5,20 (s, 2H), 5,23 (s, 2H), 6,66 (s, 2H), 6.89 in-6,92 (m, 2H), 7,00 (s, 1H), 7,10-7,22 (m, 3H).

Elemental analysis (C21H21Cl2N3O2S0,15H2O)

Calculated (%): C 55,52 H 4,99 9,25 N S 7,05 Cl 15,61

Found (%): C is 55.74 H of 5.05 N 8,77 S 6,84 Cl 15,50

Connection 1-46 received by the method described in example 45 synthesis of Compounds 1-45. NMR data are given only for intermediate connection.

The intermediate connection:

1H-NMR (CDCl3-TMS) million D.: 1,31 (d, J=6.6 Hz, 6H), 3,24 (Sept., 1H), 4,32 (s, 2H), 5,24 (s, 3H), 6,80-7,27 (m, 9H), 7.62mm (width, 1H).

Connection 1-46, so pl. 96-98oC.

1H-NMR (CDCl3-TMS) million D.: of 1.29 (d, J=7.2 Hz, 6H), 3,20 (Sept., 1H), 4,50 (width, 2H), further 5.15 (s, 2H), with 5.22 (s, 2H), 6,76-7,26 (m, 9H).

Elemental analysis (C21H22ClN3O2S 0,6 H2O)

Calculated (%): 59,09 H 5,49 N 9,85 S 7,51 Cl 8,32

Found (%): C 59,33 H 5,44 N 9,68 S 7,17 Cl 7,87

Example 47

Synthesis of 1-benzyl-2-carbamoyloxymethyl-4-isopropyl-5-(3 - nitrophenylthio)-1H-imidazole (Compound 1-47)

Connection 1-47 received by the method described in example 45 synthesis of Compounds 1-45. NMR data are given only for intermediate connection.

The intermediate connection:

1H-NMR (CDCl3-TMS) million D.: 1,32 (d, J=6.9 Hz, 6H), 3,22 (Sept., 1H), or 4.31 (s, 2H), 5,28 (s, 2H), 6,83-6,86 (m, 2H), 7,14-7,27 (m, 5H), and 7.6 (s, 1H), 7,75 (width, 1H), of 7.90 (DD., J= 11,4 Hz, 1.2 Hz, 1H).

Connection 1-47, so pl. 58oC

1H-NMR (CDCl3-TMS) million D.: of 1.29 (d, J=7.2 Hz, 6H), 3,17 (Sept., 1H), 4,57 (Shir. , 2H), total of 5.21 (s, 2H, in), 5.25 (s, 2H), 6.87 in-6,90 (m, 2H), 7,07-7,16 (mV>O4S 0,6 H2O0,5Et2O)

Calculated (%): C 58,00 of 6.02 H N 11,77 S OF 6.73

Found (%): C 57,91 H 5,72 N 11,73 S Of 6.71.

Example 48

Synthesis of 1-allyl-2-carbamoyloxymethyl-4-isopropyl-5-(3 - nitrophenylthio)-1H-imidazole (Compound 1-48)

Connection 1-48 received by the method described in example 45 synthesis of Compounds 1-45. NMR data are given only for intermediate connection.

The intermediate connection

1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J= 9.9 Hz, 6H), 3.15 in (Sept., 1H), 4,42 (s, 2H), 4,67-4,69 (m, 2H), 4,84 (dt, J=20,1 Hz, 1.5 Hz, 1H), 5,07 (d, J= 11.7 Hz, 1H), from 5.29 (s, 2H), 5,62-5,80 (m, 1H), 7,42 (t, J=7.8 Hz, 1H), 7,78 (t, J=2.1 Hz, 1H), to 7.99 (DD, J=10.5 Hz, 0.9 Hz, 1H), 8,06 (Shir. 1H).

Connection 1-48, so PL 124-125oC

1H-NMR (CDCl3-TMS) million D.; 1.27mm (d, J=6.9 Hz, 6H), 3.15 in (Sept., 1H), 4,65 - of 4.66 (m, 2H), 4,88 (DD, J=17 Hz, 0.6 Hz, 1H), of 5.05 (DD, J=11,1 Hz, 0.9 Hz, 1H), 5,19 (s, 2H), 5,64-5,78 (m, 1H), 7,41 (t, J=7.8 Hz, 1H), 7,81 (t, J=1.8 Hz, 1H), 7,98 (DD, J=11,1 Hz, 0.9 Hz, 1H).

Elemental analysis (C17H20N4O4S H2O0,5-Et2O)

Calculated (%): C 52,87 H 6,32 N 12,99 S 7,43

Found (%): C 52,91 H 6,00 N S 12,65 7,24.

Example 49

Synthesis of 2-carbamoyloxymethyl-1-ethyl-4-isopropyl-5-(3 - nitrophenylthio)-1H-imidazole (Compound 1-49)

Connection 1-49 received by the method described in example 45 synthesis Connect the

1H-NMR (CDCl3-TMS) million D.: 1,21 (t, J=7.5 Hz, 3H), 1,24 (d, J=7.2 Hz, 6H), 3,13 (Sept., 1H), 4,13 (sq, J=7.5 Hz, 2H), 5,33 (s, 2H), 7,25 (dt, J= 8,1 Hz, 0.9 Hz, 1H), 7,43 (t, J=7.8 Hz, 1H), 7,94 (t, J=1.8 Hz, 1H), to 7.99 (DD, J=2,4 Hz and 8.4 Hz, 1H), 8,20 (width, 1H).

Connection 1-49, so pl. 131-137oC

1H-NMR (CDCl3-TMS) million D.: of 1.20 (t, J=7.5 Hz, 3H), of 1.26 (d, J=6.9 Hz, 6H), 3,14 (Sept., 1H), 4,03 (sq, J= 7.5 Hz, 2H), 4.75 in (lat., 2H), 5,23 (s, 2H), 7,27 (m, 1H),7,42 (t, J= 7.8 Hz, 1H), 7,83 (t, J=2.1 Hz, 1H), 7,98 (DD, J=9.6 Hz, 1.2 Hz, 1H).

Elemental analysis (C16H20N4O4S)

Calculated (%): C 52,73 H of 5.53 shed 15.37 N S 8,80

Found (%): C 52,83 H 5,61 N 15,07 S 8,53.

Example 50

Synthesis of 2-carbamoyloxymethyl-4-isopropyl-5-(3-nitrophenylthio)-1 - n-propyl-1H-imidazole (Compound 1-50)

Connection 1-50 received by the method described in example 45 synthesis of Compounds 1-45. NMR data are given only for intermediate connection.

The intermediate connection:

1H-NMR (CDCl3-TMS) million D.: 0,88 (t, J= 7.2 Hz, 3H),1,24 (d, J= 6.9 Hz, 6H), 1,52-of 1.62 (m, 1H), 3,12 (Sept., 1H) of 3.94 (t, J= 8,1 Hz, 2H), of 4.44 (s, 2H), 5,32 (s, 2H), 7,24 (dt, J= 8,1 Hz, 0.6 Hz, 1H), 7,43 (t, J= 8,4 Hz, 1H), to 7.77 (t, J= 1.8 Hz, 1H), to 7.99 (DD, J=2.1 Hz, 9.3 Hz, 1H).

Connection 1-50, so pl. 120-124oC

1H-NMR (CDCl3-TMS) million D.: of 0.87 (t, J= 9.9 Hz, 3H), 1,25 (d, J= 7.2 Hz, 6H), 1,50-of 1.65 (m, 2H), 3,12 (Sept., 1H), 3,91 (dt, J= 8,1 G is 2">

Elemental analysis (C17H22N4O4S)

Calculated (%): C 53,95 H 5,86 N 14,80 S OF 8.47

Found (%): C 53,83 H 5,85 N 14,70 S 8,61.

Example 51

Synthesis of 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl - 1-n-propyl-1H-imidazole (Compound 1-51)

Connection 1-51 received by the method described in example 45 synthesis of Compounds 1-45. So pl. 110-112oC.

1H-NMR (CDCl3-TMS) million D.: 0,88 (t, J=7.4 Hz, 3H), 1,25 (d, J= 7,0 Hz, 6H), 1,50-of 1.65 (m, 2H), 3,09 (Sept., 1H) 3,85-3,93 (m, 2H), 4,71 (width, 2H), with 5.22 (s, 2H), 6,79 (d, J= 2 Hz, 2H), 7,12 (t, J=1.6 Hz, 1H).

Elemental analysis (C17H21Cl2N3O2S0,6H2O)

Calculated (%): C 49,42 H 5,42 N 10,17

Found (%):. C 49,14 H A 5.25 N 10,07.

Example 52

Synthesis of 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-1-ethyl-4 - isopropyl-1H-imidazole (Compound 1-52)

Connection 1-52 received by the method described in example 45 synthesis of Compounds 1-45. So pl. 148-149oC.

1H-NMR (CDCl3-TMS) million D.: 1,21 (t, J= 7.2 Hz, 3H), of 1.26 (d, J=7.2 Hz, 6H), 3,11 (Sept., 1H), 4.00 points (sq, J=7.2 Hz, 2H), 4,76 (width, 2H), with 5.22 (s, 2H), for 6.81 (d, J=1.8 Hz, 2H), 7,12 (t, J=1.8 Hz, 1H).

Elemental analysis (C16H19Cl2N3O2S)

Calculated (%): C 48,37 H 5,07 of 10.58 N S 8,07 Cl 17,85

Found (%); C 48,32 H 4,94 N 10,45 S 8,28 Cl 17,88.


Connection 1-53 received by the method described in example 45 synthesis of Compounds 1-45. So pl. 98-100oC.

1H-NMR (CDCl3-TMS) million D.:1,19 (t, J=7.4 Hz, 3H), 1,25 (d, J= 6.6 Hz, 6H), 3.15 in (Sept., 1H), 4.00 points (sq, J= 7,4 Hz, 2H), 4,77 (width, 2H), a total of 5.21 (s, 2H), 6,80-7,16 (m, 4H).

Example 54

Synthesis of 2-carbamoyloxymethyl-5-(3-chlorophenylthio)-4-isopropyl - 1-n-propyl-1H-imidazole (Compound 1-54)

Connection 1 - 54 was obtained by the method described in example 45 synthesis of Compounds 1-45. So pl. 110-112oC.

1H-NMR (CDCl3-TMS) million D.: 0,88 (t, J=7.5 Hz, 3H), 1.27mm (d, J= 6.6 Hz, 6H), 1.56 to of 1.64 (m, 2H), 3.15 in (Sept., 1H), 3,86-3,93 (m, 2H), 4,76 (width, 2H), 5,23 (s, 2H), for 6.81-7,20 (m, 4H).

Elemental analysis (C17H22ClN3O2S 0,2 H2O)

Calculated (%): C 54,96 H between 6.08 N 11,31 S 8,63 Cl 9,54

Found (%): C 54,89 H 5,97 N 11,28 S 8,43 Cl 10,06

Example 55

Synthesis of 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl - 1-(1,1,1-triptorelin)-1H-imidazole (Compound 1-55)

Connection 1-55 received by the method described in example 45 synthesis of Compounds 1-45. NMR data are given only for intermediate connection.

The intermediate connection

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J=7.2 Hz, 6H), is 3.08 (Sept., 1H), to 4.38 (s, 2H), a 4.83 (sq, J=7.5 Hz, 2H), 5,31 (s, 2H), 6.75 in (d, J=1.8 Hz, 2H), 7,15 (t, J= 1,8 GCC, 6H), 3,11 (Sept., 1H), 4,74 (width, 2H), 4,84 (sq, J= 7,6 Hz, 2H), total of 5.21 (s, 2H), 6.75 in (l, J=1.4 Hz, 2H), 7,15 (t, J=1.4 Hz, 1H), 8,21 (width, 1H).

Elemental analysis (C16H16Cl2F3N3O2S)

Calculated (%): C 43,45 H 3,65 9,50 N Cl 16,03 F 12,89 S 7,25

Found (%): C 43,41 H 3,70 N 9,37 Cl 15,88 F 12,87 S 7,24.

Example 56

Synthesis of 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-1-vermeil - 4-isopropyl-1H-imidazole (Compound 1-56)

Connection 1-56 received by the method described in example 45 synthesis of Compounds 1-45. NMR data are given only for intermediate connection.

The intermediate connection

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J= 7,0 Hz, 6H), 3.15 in (Sept., 1H), 4,42 (s, 2H), equal to 6.05 (d, J=52 Hz, 2H), at 6.84 (d, J= 1.8 Hz, 2H), 7,16 (t, J= 1.8 Hz, 1H), 8,11 (width, 1H).

Connection 1-56. So pl. 166-169oC

1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J=7.2 Hz, 6H), and 3.16 (Sept., 1H), from 5.29 (s, 2H), 6,04 (d, J=52 Hz, 2H), 6,85 (d, J= 1.8 Hz, 2H), 7,14 (t, J= 1.8 Hz, 1H).

Elemental analysis (C15H16Cl2FN3O2S)

Calculated (%): C 45,93 H 4,11 N 10,71 Cl 18,08 F 4,84 S 8,17

Found (%): C 45,62 H 4,11 N 10,71 Cl 18,36 F 5,08 S 8,16.

Example 57

Synthesis of 2-carbamoyloxymethyl-1-ethyl-5-(3-forfinally)-4 - isopropylamino-1H-imidazole (Compound 1-57)

Compound 1-57 got way opican, = 7.2 Hz, 3H), 1,25 (d, J= 7,0 Hz, 6H), is 3.08-up 3.22 (m, 1H), 4,03 (sq, J= 7.2 Hz, 2H), 4,60-4,80 (width, 2H), a total of 5.21 (s, 2H), 6,60-6,86 (m, 3H), 7,15-7,25 (m, 1H).

Example 58

Synthesis of 2-carbamoyloxymethyl-5-(3,5-differenlty)-1-ethyl-4 - isopropyl-1H-imidazole (Compound 1-58)

Compound 1-58 received by the method described in example 45 synthesis of Compounds 1-45. So pl. 128-130oC.

1H-NMR (CDCl3-TMS) million D.; to 1.21 (t, J=7.2 Hz, 3H), 1,25 (d, J= 7,0 Hz, 6H), 3,11 (Sept., 1H), 3,98 (sq, J= 7.2 Hz, 2H), 4,60-4,84 (width, 2H), and 5.30 (s, 2H), 6,60-only 6.64 (m, 3H).

Example 59

Synthesis of 2-carbamoyloxymethyl-4-(3-chlorophenylthio)-5-isopropyl-1 - methylimidazole (Compound 1-59)

In 5 ml of anhydrous tetrahydrofuran was dissolved 200 mg (0.67 mmol) [4-(3-chlorophenylthio)-5-isopropyl-1-methyl-1H-imidazol-2-yl] methanol (Compound 1-38), and to the resulting mixture, cooling at -40oC, was added 190 mg (1.0 mmol) trichloroacetimidate. After 10 minutes the mixture was heated to 0oC and stirred at this temperature for 10 minutes. To the reaction mixture was added ice water, after which the mixture was neutralized with saturated aqueous sodium bicarbonate solution and was extracted with ethyl acetate. The organic layer was washed with water and dried with sodium sulfate. The solvent was concentrated under reduced pressure, and the residue on the operating mixture was added water, were extracted with methylene chloride, and the extract was washed with water and dried with sodium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel (ethyl acetate). The resulting product was recrystallized from ethyl acetate/isopropyl ether, resulting in a received 180 mg of target compound (Compound 1-59) (yield 79%). So pl. 145-146oC.

1H-NMR (CDCl3-TMS) million D.: of 1.33 (d, J=7.2 Hz, 6H), 3,24 (Sept., 1H), 3,68 (s, 3H), 4,81 (width, 2H), 5,19 (s, 2H), 6,97-to 7.15 (m, 4H).

IR (Nujol") 3382, 3160, 1741, 1715 cm-1< / BR>
Elemental analysis (C15H18ClN3O2S)

Calculated (%): C 53,01, H 5,34 N 12,36 S 9,43 Cl 10,43

Found (%): C 53,13 H 5,42 To 12.28 N S 9,41 The 10.40 Cl.

Example 60

Synthesis of 2-{[5-(3,5-dichlorophenylthio)-4-isopropyl-1-Mei - 2-yl]methoxy}acetic acid ethyl ester (Compound 1-60)

In anhydrous dimethylformamide (10 ml) was dissolved 500 mg (mmol 1,60) [5-(3', 5'-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2 - yl] methanol (Compound 1-8), and then at room temperature was added 180 mg (4,50 mmol) of 60% sodium hydrate, and the mixture was stirred for 5 minutes. To this solution was added 452 mg (2,70 mmol) 2-methyl bromide-1,3-dioxolane, and the mixture was heated 2 hours at 50oC. Organizes the Ali using chromatography on silica gel (ethyl acetate), as a result, we received 156 mg 5-(3,5-dichlorophenylthio)-2-(1,3-dioxolane-2-intoximeter)-4 - isopropyl-1-methyl-1H-imidazole (23a) in the form of oily substance (yield 25%).

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J=6.8 Hz, 6H), 3,11 (Sept., 1H), only 3.57 (s, 3H), 3,83-3,98 (m, 4H), 4,24 (d, J= 4.0 Hz, 2H), 4,74 (s, 2H), of 5.05 (t, J=4.0 Hz, 1H), 6,78 (m, 2H), 7,10 (m, 1H).

In a mixture of methanol (1 ml) and 6 H of hydrochloric acid (1 ml) was dissolved 156 mg (from 0.37 mmol) of 5-(3,5-dichlorophenylthio)-2-(1,3-dioxolane-2 - intoximeter)-4-isopropyl-1-methylimidazole (23a), and the mixture was stirred 3 hours at room temperature. To reaktsionnoi mixture was added saturated aqueous sodium bicarbonate solution to neutralize and was extracted with methylene chloride. The organic layer was washed with water and dried with sodium sulfate. The solvent is kept under reduced pressure, and the residue was fractionally using chromatography on silica gel (ethyl acetate), resulting in a received 39 mg of { [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H - imidazol-2-yl] methoxy]acetaldehyde (24A) in the form of oily substance (yield 28%).

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J=7,0 Hz, 6H),3,12 (Sept., 1H), 3,63 (s, 3H), 4,23 (s, 2H), and 4.75 (s, 2H), for 6.81 (m, 2H), 7,13 (m, 1H), for 9.64 (s, 1H).

In ethanol (6 ml) was dissolved 220 mg (0.59 mmol) of {[5-(3,5-diclofena sodium, and the resulting mixture stirred 15 minutes. The reaction mixture was slightly acidified with acetic acid. And again for neutralization was added saturated aqueous sodium bicarbonate solution, after which the mixture was extracted with methylene chloride. The extract was washed with water and dried with sodium sulfate. The solvent is kept under reduced pressure, and the residue was fractionally using chromatography on silica gel (ethyl acetate). The product was recrystallized from n-hexane and received 144 mg of 2-{ [5-(3,5 - dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2 - yl]methoxy} ethanol (25A) (yield 65%) so pl. 89-90oC.

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J= 7,0 Hz, 6H), 3,12 (Sept., 1H), 3,28 (Shir. , 1H), 3,54 (s, 3H), 3,65-of 3.78 (m, 4H), 4.72 in (s, 2H), 6,79 (m, 2H), 7,12 (m, 1H).

Elemental analysis (C16H20Cl2N2O2S)

Calculated (%): C 51,20 lower than the 5.37 H N 7,46 S 8,54 Cl rate 18.89

Found (%): C 51,00 H 5,41 N 7,43 S 8,46 Cl 19,15.

To anhydrous methylenechloride solution (5 ml) of 200 mg (0.5 mmol) 2-{ [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2 - yl] methoxy}ethanol (25A) was added 161 mg (1,60 mmol) of triethylamine. Then, with ice cooling was added 63 mg (0.8 mmol) acetylchloride, and the resulting mixture was stirred at the same temperature for 15 minutes. To the reaction see the house. The extract was washed with water and dried with sodium sulfate. The solvent is kept under reduced pressure, and the residue was purified by chromatography on silica gel (ethyl acetate:n-hexane = 1:1), resulting in the received 200 mg of 2-{[5-(3,5-dichlorophenylthio)- 4-isopropyl-1-Mei-2-yl] -methoxy} acetic acid ethyl ester (Compound 1-60) in the form of oily substance (yield 90%),

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J=7,0 Hz, 6H), was 2.05 (s, 3H), 3,12 (Sept. , 1H), only 3.57 (s, 3H), 3,68 (t, J= 4.6 Hz, 2H), 4,22 (t, J=4.6 Hz, 2H), 4,70 (s, 2H), 6,78 (m, 2H), 7,12 (m, 1H).

Example 61

Synthesis of (2-carbamoylated)ethoxy-5-(3,5-dichlorophenylthio)-4 - isopropyl-1-methyl-1H-imidazole (Compound 1-61)

Anhydrous tertrahydrofuran ring solution (5 ml) 200 mg (0.50 mmol) 2-{ [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]methoxy}ethanol (25A) was cooled to -40oC and was added 150 mg (0.8 mmol) trichloroacetimidate. The resulting mixture was stirred at this temperature for 10 minutes. Then the mixture was heated to 0oC and stirred at this temperature for 10 minutes. To the reaction mixture was added ice water, after which the mixture was extracted with ethyl acetate, and the organic layer was washed with water and dried with sodium sulfate. Solvent are condensed under reduced pressure, and on the ri 50oC. the Reaction mixture was cooled to room temperature, and then added water and was extracted with methylene chloride. The extract was washed with water and was extracted with methylene chloride. The extract was washed with water and dried with sodium sulfate. The solvent is kept under reduced pressure, and the residue was purified by chromatography on silica gel (ethyl acetate). The resulting product was recrystallized from n-hexane and received 197 mg of target compound (Compound 1-61) (yield 88%). So pl. 102-103oC.

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J=7,0 Hz, 6H), 3,12 (Sept., 1H), of 3.56 (s, 3H), of 3.69 (t, J= 4,8 Hz, 2H), 4,24 (t, J=4,8 Hz, 2H), 4,66 (width, 2H), 4,70 (s, 2H), 6,79 (m, 2H), 7,11 (m, 1H).

IR (Nujol") 3360, 3160, 1696, 1079 cm-1< / BR>
Elemental analysis (C17H21Cl2N3O3S)

Calculated (%): C 48,81 H 5,06 N 10,04 S 7,66 Cl 16,95

Found (%): C 48,73 H 5,09 To 9.93 N S Of 7.68 Cl 16,66.

Example 62

Synthesis of 2-{[5-(3,5-dichlorophenylthio)-1-ethyl-4-isopropyl-1H - imidazol-2-yl] methoxy}acetic acid ethyl ester (Compound 1-62)

5-(3,5-dichlorophenylthio)-2-(1,3-dioxolane-2-intoximeter)-1 - ethyl-4-isopropyl-1H-imidazole (23b) was obtained by the method described in example 60 synthesis of compound (23a), oily substance.

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J=6.8 Hz, 6H), 1,24 (chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl] methoxy} acetaldehyde (24b) was obtained from (23b). The oily product.

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J = 7,0 Hz, 6H), of 1.26 (t, J = 7.0 Hz, 3H), 3,09 (Sept., 1H), 4,07 (sq, J = 7,0 Hz, 2H), 4,23 (s, 2H), 4,74 (s, 2H), for 6.81 (m, 2H), 7,16 (m, 1H), 9,65 (s, 1H).

2-{ [5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2 - yl] methoxy} ethanol (25b) was obtained from {[5-(3,5-dichlorophenylthio)-4 - isopropyl-1-methyl-1H-imidazol-2-yl]methoxy}acetaldehyde (24b). So pl. 93-94oC.

1H-NMR (CDCl3-TMS) million D.: 1,22 (t, J = 7.4 Hz, 3H), 1,25 (d, J = 7,0 Hz, 6H), 3,10 (Sept., 1H), 3,52 (width, 1H), 3,71-with 3.79 (m, 4H), 3,97 (sq, J= 7,4 Hz, 2H), 4,71 (s, 2H), to 6.80 (m, 2H), 7,12 (m, 1H).

IR (Nujol") 3274, 1560 cm-1< / BR>
Elemental analysis (C17H22Cl2N2O2S)

Calculated (%): C 52,44 H 5,70 N 7,19 S 8,24 Cl 18,21

Found (%): C 51,98 H 5,76 N 7,14 S Cl 8,10 18,08

Compound 1-62 was obtained from 2-{[5-(3,5-dichlorophenylthio)-4 - isopropyl-1-methyl-1H-imidazol-2-yl] methoxy} ethanol (25b) by the method described in example 60 synthesis of Compound 1-60. An oily substance.

1H-NMR (CDCl3-TMS) million D.: 1,24 (t, J = 7.2 Hz, 3H), 1,25 (d, J=6.8 Hz, 6H), was 2.05 (s, 3H), 3,09 (Sept., 1H), 3,70 (t, J= 4.6 Hz, 2H), 4,01 (sq, J = 7.2 Hz, 2H), 4,23 (t, J = 4.6 Hz, 2H), 4,69 (s, 2H), to 6.80 (m, 2H), 7,11 (m, 1H).

IR (Nujol") 1741, 1563, 1231 cm-1.

Example 63

Synthesis of 2-(2-carbamoyloximes)methyl-5-(3,5-dichlorophenylthio the re 61 for the synthesis of Compound 1-61.

1H-NMR (CDCl3-TMS) million D.: 1,24 (t, J=7.0 Hz, 3H), 1,25 (d, J=7,0 Hz, 2H), 4,22-4.26 deaths (m, 2H), 3,09 (Sept., 1H), 3,69 - to 3.73 (m, 2H), 4.00 points (kV, J= 7,0 Hz, 2H), 4,22-4.26 deaths (m, 2H), 4,69 (s, 2H), 4,79 (width, 2H), to 6.80 (m, 2H), 7,12 (m, 1H).

IR (Nujol") 3348, 3184, 1725, 1563, 1324 cm-1.

Example 64

Synthesis of 2-{[4-0,5-dichlorophenylthio)-5-isopropyl-1-methyl-1H - imidazol-2-yl] methoxy}acetic acid ethyl ester (Compound 1-64)

4-(3,5-Dichlorophenylthio)-2-(1,3-dioxolane-2-intoximeter)-5 - isopropyl-1-methyl-1H-imidazole (23a') was obtained from [4-(3,5-dichlorophenylthio)-5-isopropyl-1-methyl-1H-imidazol-2-yl] methanol as described in example 60 synthesis of (23a), in the form of an oily substance.

1H-NMR (CDCl3-TMS) million D.: 1,32 (d, J=7.2 Hz, 6H), 3,21 (Sept., 1H), of 3.56 (d, J= 4.0 Hz, 2H), 3,71 (s, 3H), of 3.80-4.00 points (m, 4H), 4,70 (s, 2H), of 5.05 (t, J=4.0 Hz, 1H), 6,91 (m, 2H),? 7.04 baby mortality (m, 1H).

{ [4-(3,5-dichlorophenylthio)-5-isopropyl-1-methyl-1H-imidazol-2-yl] methoxy} acetaldehyde (24A') was obtained as an oily substance from 4-(3,5-dichlorophenylthio)-2-(1,3-dioxolane-2 - intoximeter)-5-isopropyl-1-methyl-1H-imidazole (23a') by the method described in example 60 (24).

1H-NMR (CDCl3-TMS) million D.: of 1.34 (d, J= 7.2 Hz, 6H), 3,22 (Sept., 1H), of 3.78 (s, 3H), 4,25 (s, 2H), 4,70 (s, 2H), 6.89 in (m, 2H), 7,05 (m, 1H), 9,62 (s, 1H).

2-{ [4-(3,5-dichlorophenylthio)-5-isopropyl-1-methyl-1H-imidazol-2 - yl] methoxy} etano is SUP>H-NMR (CDCl3-TMC) million D.: of 1.33 (d, J=7.2 Hz, 6H), 2,30 (width, 1H), 3,21 (Sept. , 1H), 3,59-of 3.78 (m, 4H), 3,70 (s, 3H), of 4.66 (s, 2H), 6,91 (m, 2H), 7,05 (m, 1H).

Elemental analysis (C16H20Cl2N2O2S)

Calculated (%); C 51,20 lower than the 5.37 H N 7,46 S 8,54 Cl rate 18.89

Found (%): C 51,18 H 5,38 of 7.55 N S 8,75 Cl 18,80

Connection 1-64 received by the method described in example 60 synthesis of Compound 1-60, in the form of an oily substance.

1H-NMR (CDCl3-TMS) million D.: of 1.33 (d, J=7.2 Hz, 6H), of 2.08 (s, 3H), 3,21 (Sept. , 1H), 3,69 (t, J=4.6 Hz, 2H), 3,70 (s, 3H), is 4.21 (t, J= 4.6 Hz, 2H) and 4.65 (s, 2H), 6,91 (m, 2H), 7,05 (m, 1H).

IR (Nujol") 1738, 1563, 1232 cm-1.

Example 65

Synthesis of (2-carbamoylated)ethoxymethyl-4-(3,5-dichlorophenylthio)-5 - isopropyl-1-methyl-1H-imidazole (Compound 1-65)

Compound 1-65 received in the form of oily substances from an alcohol compound (25A'), synthesized by the method described in example 61 to obtain Compound 1-61.

1H-NMR (CDCl3-TMS) million D.: of 1.33 (d, J= 7.2 Hz, 6H), 3,21 (Sept., 1H), 3,67-and 3.72 (m, 2H), 3,70 (s, 3H), 4,21-of 4.25 (m, 2H), of 4.66 (s, 2H), 4,73 (Shir. , 2H), 6,91 (m, 2H), 7,05 (m, 1H).

Example 66

Synthesis of 2-aminomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1 - methylimidazolidine (Compound 1-66)

To anhydrous dimethylformamide solution (50 ml) containing 22,5 g (67 who chloride, and the resulting mixture was stirred for 1 hour at room temperature. The reaction mixture was concentrated under reduced pressure and to the residue was added ethyl acetate for extraction. The extract was neutralized with saturated aqueous sodium bicarbonate solution and was dried with magnesium sulfate. The solvent is kept under reduced pressure, resulting in a received 23.7 g of 2-chloromethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methylimidazole (28a) (yield about 100%). So pl. 110-111oC.

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J=7,0 Hz, 6H), 3,12 (Sept., 1H) and 3.59 (s, 3H), to 4.73 (s, 2H), 6,79 (d, J= 1.8 Hz, 2H), 7,13 (t, J=1.8 Hz, 1H).

Elemental analysis (C14H15Cl3N2S)

Calculated (%): C 48,08 H 4,32 N 8,01

Found (%): C 47,98 H 4,39 N 8,12

To anhydrous dimethylformamide solution (70 ml) containing 23.7 g of 2-chloromethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H - imidazole (28a), was added 5.30 g of sodium azide, and the mixture was stirred by heating at 80oC for 16 hours. Then the reaction mixture was added to ice water and was extracted with diethyl ether. The organic layer was washed with water and dried with magnesium sulfate. The solvent is kept under reduced pressure and received 24.2 g of 2-azidomethyl - 5-(3,5-dichlorophenylthio)-4-ISO is of 1.26 (d, J=6.6 Hz, 6H), 3,13 (Sept., 1H), 3,55 (s, 3H), 4,35 (s, 2H), 6,79 (d, J= 2 Hz, 2H), 7,13 (t, J=2.0 Hz, 1H).

Elemental analysis (C14H15Cl2N5S)

Calculated (%): C 47,20 H 4,24 N 19,66 S 9,00 Cl 19,90

Found (%): C Is 47.24 H Or 4.31 N 19,60 S 8,93 Cl 20,12.

To anhydrous tertrahydrofuran ring solution (60 ml) and 24.2 g of 2-azidomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole (29A) was added, the cooling in this ice and 19.6 g of triphenylphosphine, and the mixture was stirred for 4 hours at room temperature. After complete reaction (disappearance 29A), which was confirmed by thin-layer chromatography (TLC) (silica gel, methylene chloride: ethyl acetate = 10:1) was added 50 ml of water, after which the mixture is stirred at room temperature for 1.5 hours and left overnight. Tetrahydrofuran drove under reduced pressure and to the residue was added 400 ml of 3 H hydrochloric acid. When flushing diethyl ether from hydrochloric sdoia has precipitated crystals. These crystals were collected by filtration and neutralized with saturated aqueous sodium bicarbonate solution. The mixture was extracted with diethyl ether. The aqueous layer was neutralized with saturated aqueous sodium bicarbonate solution and was extracted with diethyl ether. These essential was extractable 20.6 g of 2-aminomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl - 1H-imidazole (30A) (yield 92%). So pl. 86-87oC.

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J=6.9 Hz, 6H), 3,11 (Sept., 1H), 3,52 (s, 3H), 4,01 (s, 2H), 6,80 (d, J= 1.8 Hz, 2H), 7,11 (t, J=1.8 Hz, 1H).

Elemental analysis (C14H17Cl2N3S)

Calculated (%): C 50,91 H 5,19 N 12,72 S 9,71 Cl 21,47

Found (%): C 50,88 H 5,24 H 12,53 S 9,49 Cl 21,51.

The ethyl acetate was dissolved 20.6 g of 2-aminomethyl-5-(3,5 - dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole (30A), and then was added an ethyl acetate solution of 16.9 g of oxalic acid, and the resulting mixture was heated. After the reaction mixture was cooled, and the crystals were filtered. Then the crystals are recrystallized from ethanol and obtained 19.3 g of target Compound 1-66 (yield 60%).

So pl. 162-163oC.

Elemental analysis (C14H17Cl2N3S(COOH)20.5 H2O)

Calculated (%): C 43,05 H 4,46 N 8,86 S 6,76 Cl 14,95

Found (%): C 42,96 H 4,47 N 9,06 S 6,74 Cl 14,86

2-aminomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H - imidazole (30A) get the corresponding hydrochloride by the method described in this example. So pl. 123-125oC.

Elemental analysis (C14H17Cl2N3SHCl0,25H2O)

Calculated (%): C 41,24 H 4,82 N 10,31 S 7,86 Cl 34,78

Found (%): C 41,10 H 4,74 N 10,27 S 7,93 Cl 35,05.

Example 67
oC.

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J=7,0 Hz, 6H), 3,14 (Sept., 1H), 3,60 (s, 3H), to 4.73 (s, 2H), 7,19 (d, J= 7,0 Hz, 1H), 7,43 (t, J= 7.8 Hz, 1H), 7,85 (t, J=2.0 Hz, 1H), 8,00 (d, J=7.8 Hz, 1H).

Elemental analysis (C14H16ClN3O2S)

Calculated (%): C 51,61 H 4,95 N 12,90 S 9,84 Cl 10,88

Found (%): C 51,61 H 5,00 Was 12.75 N S 9,88 Cl 10,89.

2-Azidomethyl-4-isopropyl-1-methyl-5-(3-nitrophenylthio)-1H-imidazole (29b) was obtained from 2-chloromethyl-4-isopropyl-1-methyl-5-(3-nitrophenylthio)- 1H-imidazole (28b) by the method described in example of synthesis of compound (29A).

So pl. 100-101oC.

1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J=7,0 Hz, 6H), 3.15 in (Sept., 1H), of 3.56 (s, 3H), of 4.54 (s, 2H), 7,19 (d, J=8.0 Hz, 1H), 7,43 (t, J= 8.0 Hz, 1H), to 7.84 (t, J= 2.2 Hz, 1H), 8,00 (d, J= 8.0 Hz, 1H).

Elemental analysis (C14H16N6O2S)

Calculated (%): C 50,59 H 4,85 N 25,28 S 9,65

Found (%): C 50,63 H 4,88 N 24,94 S For 9.64.

The target compound 1-67 received by the method described in example 66 synthesis of Compound 1-66. So pl. 77-78oC.

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J=7,0 Hz, 6H), 3,14 (Sept., 1H), 3,53 (s, 3H), 4.00 points (s,2H), 7,22 (d, J=8,2 Hz, 1H), 7,83 (t, J=2.4 Hz, 1H), of 7.97 (d, J=8,2 Hz, 1H).

Elemental analysis (C14H18N4O2 2-aminomethyl-1-n-butyl-5-(3,5-dichlorophenylthio)-4 - isopropyl-1H-imidazole (Compound 1-68)

Compound 1-68 were obtained from [5-(3,5-dichlorophenylthio)-1-n-butyl-4 - isopropyl-1H-imidazol-2-yl] methanol (12) the method described in example 66 synthesis of Compound 1-66. An oily substance.

1H-NMR (CDCl3-TMS) million D.: 0,86 (t, J=7.2 Hz, 3H), of 1.23 to 1.34 (m, 2H), 1,24 (d, J= 7.2 Hz, 6H), 1,47 is 1.58 (m, 2H), 3,09 (Sept., 1H), a 3.87 (t, J=7,6 Hz, 2H), 3.96 points (s, 3H), to 6.80 (d, J=1.8 Hz, 2H), 7,10 (t, J=1.8 Hz, 1H).

Example 69

Synthesis of 2-aminomethyl-5-(3-chlorophenylthio)-4-isopropyl-1-methyl-1H - imidazole hydrochloride (Compound 1-69)

2-Aminomethyl-5-(3-chlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole (30C) was obtained from 2-(3-chlorophenylthio-4-isopropyl-1-methyl)imidazolyl - 1H-methanol (12) the method described in example 66 synthesis of Compound 1-66. An oily substance.

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J=6.8 Hz, 6H), 1,78 (s, 2H), 3,14 (Sept. , 1H), 3,51 (s, 3H), 3,99 (s, 2H), for 6.81 (dt, J=7,2 Hz, 1.8 Hz, 1H), 6,93 (t, J=1.8 Hz, 1H). 7,07-7,20 (m, 2H).

Compound 1-69 was obtained from 2-aminomethyl-5-(3-chlorophenylthio)- 4-isopropyl-1-methylimidazole (30C) by the method described in example 66 synthesis of Compound 1-66.

So pl. 99-101oC.

Elemental analysis (C14H18ClN3S2 HCl0,67H2O)

Calculated (%): C 44,16 H 5,65 N 11,04 S 8,42 Cl 27,93

Found (X): C 44,19 H 5,67 N 11,09 S 8,53 Cl 27,67

Example 70

Sin,5-dichlorophenylthio)-4-isopropyl-1H - imidazole (28th) was synthesized from [1-benzyl-5-(3,5-dichlorophenylthio)-4 - isopropyl-1H-imidazol-2-yl]methanol way described in example 66 to obtain the Compound (28a), and then without purification of the synthesized compounds was obtained 2-azidomethyl-1-benzyl-5-(3,5-dichlorophenylthio)-4 - isopropylimidazole (e) by the method described in example 66 synthesis of Compound (29A). An oily substance.

1H-NMR (CDCl3-TMS) million D.: of 1.29 (d, J=10.5 Hz, 6H), and 3.16 (Sept., 1H), of 4.44 (s, 2H), 5,20 (s, 2H), to 6.67 (d, J=2.4 Hz, 2H), 6,85-to 6.95 (m, 2H), 7,02 (t, J= 2,04 Hz, 1H), 7,1-7,3 (m, 3H).

IR (Nujol") 2100 cm-1.

Connection 1-70 was obtained from 2-azidomethyl-1-benzyl-5-(3,5 - dichlorophenylthio)-4-isopropyl-1H-imidazole (e) by the method described in example 66 synthesis of Compound 1-66. Oily connection.

1H-NMR (CDCl3-TMS) million D.: of 1.28 (d, J=6.9 Hz, 6H), 1.93 and (width, 2H), 3.15 in (Sept. , 1H) 3,93 (s, 2H), 5,19 (s, 2H), 6,69 (s, 2H), 6,93 (d, J= 7.8 Hz, 2H), 7,0 (s, 1H), 7,15-7,30 (m, 3H).

Example 71

Synthesis of 2-aminomethyl-5-(3,5-dichlorophenylthio)-1-ethyl-4-isopropyl - 1H-imidazole (Compound 1-71)

Compound 1-71 was obtained by the method described in example 66 synthesis of Compound 1-66. So pl. 63-67oC.

1H-NMR (CDCl3-TMS) million D.: of 1.20 (t, J=7.0 Hz, 3H), 1,24 (d, J= 7,0 Hz, 6H), of 1.85 (s, 2H), 3,09 (Sept., 1H), 3.96 points (sq, J= 7,0 Hz, 2H), 3,99 (s, 2H), for 6.81 (d, J=1.0 Hz, 2H), 7,10 (t, J= 1.4 Hz, 1H).

Example 72

Synthesis of 2-aminomethyl-5-(3,5-diclofe the La synthesis of Compound 1-66. So pl. 99-100oC.

1H-NMR (CDCl3-TMS) million D.; 1,22 (d, J= 6.8 Hz, 6H), USD 1.43 (d, J=7,6 Hz, 6H), of 3.07 (Sept., 1H), was 4.02 (s, 2H), br4.61-of 4.75 (m, 1H), 6,80 (d, J= 1.4 Hz, 2H), 7,10 (t,J= 1.2 Hz, 1H).

Example 73

Synthesis of 2-aminomethyl-5-(3-chlorophenylthio)-1-ethyl-4 - isopropylimidazole (Compound 1-73)

Compound 1-73 was obtained by the method described in example 66 synthesis of Compound 1-66. An oily substance.

1H-NMR (CDCl3-TMS) million D.: 1,19 (t, J=7.4 Hz, 3H), 1,24 (d, J= 7,6 Hz, 6H), 2,1 (width, 2H), 3,13 (Sept., 1H), 3,97 (sq, J= 7,4 Hz, 2H), 3,99 (s, 2H), 6,80-7,19 (m, 4H).

Example 74

Synthesis of 2-aminomethyl-4-isopropyl-1-methyl-5-phenylthiazole (Compound 1-74)

2-Chloromethyl-4-isopropyl-1-methyl-5-phenylthio-1H-imidazole (28i) was obtained from [4-isopropyl-1-methyl-5-phenylthio-1H-imidazol-2-yl] methanol as described in example 66 synthesis of compound (28a). An oily substance.

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J=7.2 Hz, 6H), 3,14 (Sept., 1H) of 3.53 (s, 3H), 4,50 (s, 2H), 6,91-7,28 (m, 5H).

2-Azidomethyl-4-isopropyl-1-methyl-5-phenylthio-1H-imidazole (29i) was obtained from 2-Chloromethyl-4-isopropyl-1-methyl-5-phenyl-1H-imidazole (28i) by the method described in example 66 synthesis of compound (29A). An oily substance.

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J=7,0 Hz, 6H), 3,19 (by the way, described in example 66 synthesis of Compound 1-66. An oily substance.

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J=7,0 Hz, 6H), 1,52 (width, 2H), 3,18 (Sept., 1H), 3,51 (s, 3H), of 3.96 (s, 2H), 6,93-7,28 (m, 5H).

Example 75

Synthesis of 2-aminomethyl-1-ethyl-4-isopropyl-5-phenylthio-1H-

imidazole (Compound 1-75)

2-Chloromethyl-1-ethyl-4-isopropyl-5-phenylthiazol (28j) was obtained from [(1-ethyl-4-isopropyl-5-phenylthio)-1H-imidazol-2 - yl] methanol as described in example 66 synthesis of compound (28a). An oily substance.

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J = 7,0 Hz, 6H), 1,25 (t, J= 7.0 Hz, 3H), 3,17 (Sept., 1H), 4.04 the (sq, J= 7,0 Hz, 2H), 4,71 (s, 2H), 6,93-7,27 (m, 5H).

2-Azidomethyl-1-ethyl-4-isopropyl-5-phenylthio-1H-imidazole (29j) was obtained from 2-chloromethyl-1-ethyl-4-isopropyl-5-phenylthio-1H-imidazole (28j) by the method described in example 66 synthesis of Compound (29A). An oily substance.

1H-NMR (CDCl3-TMS) million D.: 1,21 (t, J = 7.2 Hz, 3H), 1,25 (d, J = 6.8 Hz, 6H), 3,17 (Sept., 1H), 3,98 (sq, J= 7.2 Hz, 2H), 4,49 (s, 2H), 6,92-7,27 (m, 5H).

IR (Nujol") 2094 cm-1.

Connection 1-75 was obtained by the method described in example 66 synthesis of Compound 1-66. Oily connection.

1H-NMR (CDCl3-TMS) million D.: 1,17 (t, J = 7.2 Hz, 3H), 1,24 (d, J = 7,0 Hz,5-dichlorophenylthio)-4-isopropyl-1-(2,2,2 - triptorelin)-1H-imidazole (Compound 1-76)

2-Chloromethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(2,2,2 - triptorelin)-1H-imidazole (28k) was synthesized from [5-(3,5 - dichlorophenylthio)-4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazol-2 - yl] methanol (Compound 1-33) by the method described in example 66 to obtain the Compound (28a), and then from this compound, without cleaning it, received 2-azidomethyl-5- (3,5-dichlorophenylthio)-4-isopropyl-1-(2,2,2-triptorelin)-1H - imidazole (29K) by the method described in example 66 synthesis of compound (29A). An oily substance.

1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J= 7.8 Hz, 6H), 3,10 (Sept., 1H), 4,60 (s, 2H), 4,66 (sq, J= 8.6 Hz, 2H), 6,76~is 6.78 (m, 2H), 7,14~7,16 (m, 1H).

Compound 1-76 was obtained from 2-azidomethyl-5-(3,5-dichlorophenylthio)- 4-isopropyl-1-(2,2,2-triptorelin)-1H-imidazole (29K) by the method described in example 66 synthesis of Compound 1-66. An oily substance.

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J = 7.2 Hz, 6H), to 3.09 (Sept., 1H), 4,10 (s, 2H), 4,85 (sq, J= 8.7 Hz, 2H), 6,78 (d, J = 1.8 Hz, 2H), 7,13 (t, J= 1.8 Hz, 1H).

Example 77

Synthesis of 2-aminomethyl-5-(3,5-dichlorophenylthio)-1-vermeil-4 - isopropylimidazole (Compound 1-77)

2-Azidomethyl-5-(3,5-dichlorophenylthio)-1-(permitil-4-isopropyl-1H - imidazole (29l) was obtained by the method described in example 76 synthesis of Compound (29K). An oily substance.

IR (Nujol") 2090 cm-1< / BR>
Compound 1-77 was obtained from 2-azidomethyl-5-(3,5-dichlorophenylthio)- 1-vermeil-4-isopropyl-1H-imidazole (29l) by the method described in example 66 synthesis of Compound 1-66. An oily substance,

1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J= 6.9 Hz, 6H), 1.61 of (width, 2H), 3,13 (Sept., 1H), 4,10 (s, 2H), 6,05 (sq, J = 52,5 Hz, 2H), 6,86 (d, J= 1.2 Hz, 2H), 7,13 (m, 1H).

Example 78

Synthesis of 5-(3,5-dichlorophenylthio)-2-dimethylaminomethyl-4-isopropyl - 1-methyl-1H-imidazole (Compound 1-78)

A mixture containing 0.15 g (0.43 mmol) of 2-chloromethyl-5- (3,5 - dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole (28a), 1 ml of acetonitrile and 1.5 ml of 50% aqueous solution of methylamine, stirred for 1 hour at room temperature. The reaction mixture was concentrated under reduced pressure, and the residue was extracted with diethyl ether. The extract was washed with water and saturated saline solution and dried with potassium carbonate. The solvent is kept under reduced pressure, and the residue was fractionally using chromatography on silica gel (ethyl acetate: methylene chloride 1:4), resulting in a received 0,148 g of Compound 1-78 (yield 95%). An oily substance.

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J= 6.8 Hz, 6H), 3,10 (Sept., 1H), the filing-1-methyl-1H - imidazol-2-yl] methylamino}ethanol (Compound 1-79)

Compound 1-79 was obtained by the method described in example 78 synthesis of Compound 1-78.

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J=7,0 Hz, 6H), 2,50 (width, 2H), only 2.91 (t, J= 5,2 Hz, 2H), 3,11 (Sept., 1H), 3,49 (s, 3H), of 3.65 (t, J=5,2 Hz, 2H), 3,95 (s, 2H), 6,79 (d, J= 1.8 Hz, 2H), 7,27 (t, J= 1.8 Hz, 1H).

Elemental analysis (C16H21Cl2N3OS)

Calculated (%): C 51,34 H 5,65 N 11,23 to 8.57 S Cl 18,94

Found (%): C 51,00 H 5,67 N 11,03 S 8,44 Cl 19.01 In.

Example 80

Synthesis of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol - 2-yl] acetic acid (Compound 1-80)

13.6 ml of anhydrous dimethylformamide was dissolved 4,75 g (to 13.6 mmol) of 2-chloromethyl-5-(3,5-dichlorophenylthio)-4-isopropyl - 1-methyl-1H-imidazole (28a) and 1.0 g of potassium cyanide (97,5%), and the mixture was stirred by heating at 70-75oC, within 24 hours. Then the reaction mixture was concentrated under reduced pressure and to the residue was added water. The mixture was extracted with diethyl ether, and the organic layer was three times washed with water and dried with magnesium sulfate. The solvent is kept under reduced pressure, and the residue was fractionally using chromatography on silica gel (ethyl acetate:methylene chloride = 1: 9 - 4), resulting in a received 2,43 g of [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H - imidazol-2-yl] -acetonic (d, J= 7,0 Hz, 6H), 3,12 (Sept., 1H) and 3.59 (s, 3H), of 3.97 (s, 2H), for 6.81 (d, J=1.8 Hz, 2H), 7,14 (t, J= 1.8 Hz, 1H).

Elemental analysis (C15H15Cl2N3S)

Calculated (%): C 52,95 H of 4.44 N 12,35 S 9,42 Cl 20,84

Found (%): C 52,90 H 4,48 to 12.28 N S 9,49 Cl 20,78

A suspension of 1.0 g (2.9 mmol) [5-(3,5-dichlorophenylthio)-4-isopropyl - 1-methyl-1H-imidazol-2-yl] acetonitrile (Compound 1-80A) in methanol (12 ml) was saturated, stirring under ice cooling, anhydrous hydrogen chloride, and the resulting mixture was barbotirovany with gaseous hydrogen chloride for 30 minutes at room temperature. Then the reaction mixture was heated at 60oC and purged with gaseous hydrogen chloride for 30 minutes, after which the mixture was left overnight. The solvent is kept under reduced pressure, and the residue after neutralization was added saturated aqueous sodium bicarbonate solution. Undertaking the mixture was extracted with diethyl ether. The organic layer was washed with saline and dried with magnesium sulfate, and the solvent is kept at reduced pressure. The residue was led from isopropyl ether, resulting in received of 0.68 g of methyl-[5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl - 1H-imidazol-2-yl] acetate (33). The mother liquor obtained after crystallization, purified using the are you recrystallization from n-hexane total output amounted to 0.94 g (yield 87%). So pl. 110-111oC.

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J= 7.2 Hz, 6H), 3,11 (Sept., 1H), 3,47 (s, 3H), of 3.75 (s, 3H), 3,92 (s, 2H), 6,78 (d, J= 1.8 Hz, 2H), 7,11 (t, J= 1.8 Hz, 1H).

Elemental analysis (C16H18Cl2N2O2S)

Calculated (%): C 51,48 H a 4.86 N 7,50 S 8,59 Cl 18,99

Found (%): C 51,42 H 4,85 N 7,56 S 8,61 Cl 18,80.

A mixture of methanol (1 ml), 0.10 g of methyl-[5-(3,5-dichlorophenylthio)- 4-isopropyl-1-methyl-1H-imidazol-2-yl] acetate (33) and 1 H of sodium hydroxide (0,32 ml) stirred 1.5 hours at room temperature. Then to the reaction mixture were added 0,32 ml 1 H hydrochloric acid, and the resulting crystals were filtered, washed with water, and then cooled with methanol, resulting in a received 87 mg of target Compound 1-80 (yield 90%). So pl. 118oC (decomposition).

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J= 7.2 Hz, 6H), 3.15 in (Sept., 1H), 3,50 (s, 3H), 3,88 (s, 2H), 5,70 (width, 1H), 6,83 (doctor J= 1.8 Hz, 2H), 7,26 (t, J= 1.8 Hz, 1H).

Elemental analysis (C15H16Cl2N2O2S)

Calculated (%): C 50,15 H 4,49 N 7,80 S 8,93 Cl to 19.74

Found (%): C 50,17 H 4,53 N 7,87 S 9,06 Cl 19,61.

Example 81

Synthesis of 2-(2-carbamoylated)ethyl-5-(3,5-dichlorophenylthio)-4 - isopropyl-1-methyl-1H-imidazole (Compound 1-81)

To a suspension of 0.08 g (2.1 mmol) of lithium aluminum hydride in anhydrous of diet is l-(5- (3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl] acetate (33) in diethyl ether (10 ml), stirring in the cooling conditions of the ice. After that, the reaction mixture is stirred at this temperature for 0.5 hour and then at room temperature for 1 hour and added to ice water. The ether layer was separated by decantation and the aqueous layer was extracted with diethyl ether. The ether extracts were combined, dried with magnesium sulfate, and the solvent is kept at reduced pressure. The residue was recrystallized from isopropyl ether and filtered, resulting in received of 0.58 g of 2-[5-(3,5-dichlorophenylthio)-4 - isopropyl-1-methyl-1H-imidazol-2-yl]ethanol (Compound 1-a) (yield 82%).

1H-NMR (CDCl3-TMS) million D.: 1,22 (d, J=7,0 Hz, 6H), is 2.88 (t, J=5.8 Hz, 2H), is 3.08 (Sept. , 1H), 3,42 (s, 3H), 4.09 to (t, J= 5.8 Hz, 2H), 4,70 (width, 1H), for 6.81 (d, J= 1.8 Hz, 2H), 7,12 (t, J=1.8 Hz, 1H).

Elemental analysis (C15H18Cl2N2OS)

Calculated (%): C 52,18 H a 5.25 N 8,11 S 9,29 Cl 20,53

Found (%): C 52,08 H 5,28 N 8,10 S 9,34 Cl 20,31.

Compound 1-81 was obtained from 2-[5-(3,5-dichlorophenylthio)- 4-isopropyl-1-methyl-1H-imidazol-2-yl] ethanol (Compound 1-a) by the method described in example 41 synthesis of Compounds 1-41. So pl. 177-178oC.

1H-NMR (CDCl3-TMS) million D.: of 1.23 (d, J= 6.8 Hz, 6H),3,10 (Sept., 1H), 3,12 (t, J= 6,8 Hz, 2H), 3,48 (s, 3H), 4,43 (t, J=6,8 Hz, 2H), 4, 2
S)

Calculated (%): C 49,49 H 4,93 N 10,82 S compared to 8.26 Cl 18,26

Found (%): C 49,28 H 4,92 N 10,84 S 8,33 Cl 18,05.

Example 82

Synthesis of 2-(2-amino-ethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1 - methyl-1H-imidazole (Compound 1-82)

2-(2-Chloroethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl - 1H-imidazole (37) was obtained from Compounds 1-8 in the manner described in example 66 synthesis of Compound (28a).

So pl. 101-102oC

1H-NMR (CDCl3-TMS) million D.: of 1.23 (d, J= 7,0 Hz, 6H), 3,11 (Sept., 1H), 3,23 (t, J=7,0 Hz, 2H), 3,50 (s, 3H), 3,92 (t, J= 7,0 Hz, 2H), 6,77 (d, J= 1.8 Hz, 2H), 7,10 (t, J=1.8 Hz, 1H).

Elemental analysis (C15H17Cl3N2S)

Calculated (%); C 49,53 H 4,71 N 7,70 S 8,82 Cl 29,24

Found (%): C 49,40 H 4,74 N 7,74 S 8,86 Cl 28,94

2-(2-Azidoethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl - 1H-imidazole (38) was obtained from the compound (37) the method described in example 66 synthesis of (29A).

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J= 7,0 Hz, 6H), 3,01 (t, J= 6,8 Hz, 2H), 3,11 (Sept., 1H), 3,48 (s, 3H), 3,76 (t, J= 6,8 Hz, 2H), 6,80 (d, J= 1.8 Hz, 2H), 7,11 (t, J= 1.8 Hz, 1H).

5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-2-vinyl-1H-imidazole (37) was obtained as a by-product.

So pl. 124-125oC.

1H-NMR (CDCl3-TMS) million D.: of 1.27 (d, J= 6.8 Hz, 6H), 3,13 (Sept., 1H), 3,53 (s, 3H), of 5.55 (DD, J= 11.2 Hz, 1.5 Hz, 1H), 6,28 (DD, J= is special, described in example 66 synthesis of Compound 1-66. An oily substance.

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J= 7,0 Hz, 6H), 1,60 (width, 2H), 2,88 (t, J= 7,0 Hz, 2H), 3,10 (Sept., 1H), 3,14 (t, J= 6,8 Hz, 2H), 6,79 (d, J= 1.8 Hz, 2H), 7,10 (t, J= 1.8 Hz, 1H). Oksolat Connection 1-82. So pl. 160-161oC.

Elemental analysis (C15H19Cl2N2S C2H2O4)

Calculated (%): C 47,01 H 4,87 N 9,67 S 7,38 Cl 16,32

Found (%): C 47,08 H 4,88 9,81 N S 7,45 Cl 16,04.

Example 83

Synthesis of 2-(N-acetamidomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl - 1-methyl-1H-imidazole (Compound 1-83)

In pyridine (1 ml) was dissolved 220 mg (0.67 mmol) of 2-aminomethyl-5- (3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole (30A), and then stirring at room temperature, one drop was added 82 mg (0.80 mmol) of acetic anhydride, and the reaction mixture was left overnight. The reaction mixture was concentrated under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium bicarbonate solution and then water, and dried with sodium sulfate. The solvent is kept under reduced pressure, and the crude product was washed with n-hexane and filtered, resulting in a received 210 mg of the Compound 1-83 (yield 84%). So pl. 139-141oC.

80 (d, J= 2.0 Hz, 2H), 7,13 (t, J= 2.0 Hz, 1H).

Elemental analysis (C16H19Cl2N3OS)

Calculated (%): C 50,05 H 5,50 N A 10.74 S 8,28 Cl 18,15

Found (%): C 50,40 H 5,02 N 10,86 S Scored 8.38 Cl 17,77.

Example 84

Synthesis of 5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-2 - methylaminomethyl-1H-imidazole (Compound 1-84)

To a solution of 101 mg (0.30 mmol) of 2-aminomethyl-5-(3,5-dichlorophenylthio)- 4-isopropyl-1-methyl-1H-imidazole (30A) in methanol (2 ml) was added, stirring at room temperature for 18.5 mg (0.15 mmol) of the hydrochloride of ethyl-N-methylacetamide, after which the resulting mixture was stirred at room temperature for 3 hours and left overnight. Then to the reaction mixture for neutralization was added saturated aqueous sodium bicarbonate solution, and the reaction mixture was concentrated under reduced pressure. To the residue was added methanol (10 ml) and the mixture was concentrated under reduced pressure. This procedure was repeated three times, and then to the residue was added methanol. Insoluble material was filtered, and the filtrate was purified by chromatography on silica gel (0.5% ammonia/methanol), resulting in a received 35 mg of Compound 1-84 (yield 63%). So pl. 176-178oC.

1H-NMR(CDCl3-TMS) million D.: 1,85 (d, J= 7.2 Hz, 6H), 2,10 (s, 3H), 3,55 (BR>
Calculated (%): C 49,34 H 5,70 N 14,39 S 8,23 Cl 18,27

Found (%); C 48,90 H 5,13 N 14,02 S 8,21 Cl 18,28.

Example 85

Synthesis of 5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-2 - methylaminomethyl-1H-imidazole (Compound 1-85)

To a solution of 206 mg (from 0.76 mmol) 2-aminomethyl-5-(3,5-dichlorophenylthio)- 4-isopropyl-1-methyl-1H-imidazole (30A) and 100 mg (1,14 mmol) of triethylamine in methylene chloride (3 ml) drop by drop) was added, stirring under ice cooling, 190 mg (of 0.91 mmol) of anhydride triperoxonane acid, and the mixture was stirred at room temperature. After the disappearance of the parent compounds, as evidenced by TLC, the reaction mixture was added water, and the mixture was extracted with diethyl ether. The organic layer was washed for 1 H hydrochloric acid, saturated aqueous sodium bicarbonate and water, and then dried with magnesium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel (ethyl acetate: methylene chloride = 1: 4), resulting in a received 315 ml of 5-(3,5-dichlorophenylthio)-4-isopropyl - 1-methyl-2-triptoreline-1H-imidazole (40C) (yield 97%). Recrystallized from isopropyl ether. So pl. 157-158oC.

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J= 7,0 Hz, 6H), 3,12 (Sep H16Cl2F3N3OS)

Calculated (%): C 45,08 of 3.78 H N 9,86 S 7,52 Cl 16,63 F 13,37

Found (%): C 44,90 H A 3.87 N 9,87 S Of 7.64 Cl 16,38 F 13,16.

To a solution of 286 mg (0.67 mmol) of 5-(3,5-dichlorophenylthio)-4 - isopropyl-1-methyl-2-triptoreline-1H-imidazole (40C) in anhydrous dimethylformamide (2 Il) was added in a stream of nitrogen 32 mg (0.80 mmol) of 60% sodium hydride, and the mixture was stirred for 10 minutes under ice cooling. Then was added 115 mg (0.80 mmol) under the conditions, and the resulting mixture was stirred 3 hours at room temperature. To the reaction mixture were added an aqueous solution of ammonium chloride, and the reaction was completed. The mixture was extracted with ethyl acetate, and the extract was washed with brine 3 times, and then dried with magnesium sulfate. The solvent is kept under reduced pressure, and the residue was purified by chromatography on silica gel (ethyl acetate:methylene chloride = 1:4), resulting in a received 232 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-2-(N-TRIFLUOROACETYL - N-methyl)aminomethyl-1H-imidazole (40d) (yield 79%). An oily substance.

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J= 6.8 Hz, 6H), 3,12 (Sept., 1H), 3,20 (m, 3H), 3,51 (s, 3H), of 4.83 (s, 2H), 6,74 (d, J= 1.8 Hz, 2H), 7,13 (t, J=1.8 Hz, 1H).

A mixture of 225 mg (0.51 mmol) of 5-(3,5-dichlorophenylthio)-4-isopropyl-1 - methyl-2-(N-minut at room temperature. The reaction mixture was concentrated under reduced pressure to remove methanol. The residue was extracted with diethyl ether, and the organic layer was washed with brine and was dried with potassium carbonate. The solvent is kept under reduced pressure, and received 175 mg of the Compound 1-85 in the form of an oily product. (Yield 100%).

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J= 7,0 Hz, 6H), 2.49 USD (s, 3H), 3,11 (Sept. , 1H), 3,54 (m, 3H), a 3.87 (s, 2H), 6,78 (d, J= 1.8 Hz, 2H), 7,10 (t, J= 1.8 Hz, 1H).

Example 86

Synthesis of 2-diaminomethylene-5-(3,5-dichlorophenylthio)- 4-isopropyl-1-methylimidazole (Compound 1-86)

A solution containing 100 mg (0,292 mmol) 2-aminomethyl-5-(3,5 - dichlorophenylthio)-4-isopropyl-1-methylimidazole (30A), 97 mg (0.35 mmol) of N,N-di(t-butoxycarbonyl)thiourea and 67 mg (0.35 mmol) of EDC in anhydrous dimethylformamide (0.3 ml), stirred overnight at room temperature. Then to the reaction mixture was added ice water, extracted with diethyl ether, and the extract was washed with saline and dried with magnesium sulfate. The solvent is kept under reduced pressure, and the residue was purified by chromatography on silica gel (ethyl Acetate:n-hexane = 1:2), resulting in a received 165 mg of the product of the joining of 2-[(N,N'-di-tert-bookshelve.

1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J= 6.8 Hz, 6H), 1.50 and 1,51 (x 2, N), 3,11 (Sept., 1H), 3,53 (s, 3H), 4.72 in (d, J = 5,2 Hz, 2H), 6,78 (d, J = 1.8 Hz, 2H), 7,11 (t, J = 1.8 Hz, 1H), 11,43 (width, 1H).

A solution of 150 mg of 2-[(N,N'-di-tert-butoxycarbonyl)guanidino]-5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazole (40f) in triperoxonane acid (1.5 ml) is stirred for 1 hour at room temperature. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate, washed three times with sodium hydroxide, and the organic layer was dried with potassium carbonate. The solvent is kept under reduced pressure, resulting in a received 66 mg of target compound (Compound 1-86) in the form of oily substance (yield 68%).

1H-NMR (CDCl3-TMS) million D.: 1,17 (d, J = 7,0 Hz, 6H), is 3.08 (Sept, 1H), 3,53 (s, 3H), 4,37 (s, 2H), 6.35mm (width, 2H), 6,78 (d, J = 1.8 Hz, 2H), 7,12 (t, J = 1.8 Hz, 1H).

Example 87

Synthesis of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-methanesulfonylaminoethyl-1-methyl-1H-imidazole (Compound 1-87)

Compound 1-87 was obtained by the method described in example 86 synthesis of Compound 1-86 using 30A as the source connection. So pl. 116-118oC.

1H-NMR (CDCl3-TMS) million D.: 1,22 (d, J = 7,0 Hz, 6H), 3,11 (Sept., 1H), 3,54 (s, 3H), 4,4 SUB>2
N3O2S2)

Calculated (%): 44,12 H 4,69 N 10,29 S 15,72 Cl 17,36

Found (%): 44,08 H 4,68 N 10,24 S 15,60 Cl 17,29

Example 88

Synthesis of 5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl - 2-p-toluensulfonate-1H-imidazole (Compound 1-88)

Compound 1-88 was obtained by the method described in example 86 synthesis of Compound 1-86 using 30A as the source connection. So pl. 85-87oC.

1H-NMR (CDCl3-TMS) million D.: 1,14 (d, J= 7,0 Hz, 6H), is 2.44 (s, 3H), 3.04 from (Sept. , 1H), 3,50 (s, 3H), 4,14 (d, J= 5.4 Hz, 2H), 6,03 (width, 2H), 6,77 (d, J= 1.6 Hz, 2H), 7,13 (t, J= 1.6 Hz, 1H), 7,29 (d, J= 8,2 Hz, 2H), 7,72 (d, J= 8,2, 2H).

Elemental analysis (C21H23Cl2N3O2S2)

Calculated (%): C 52,20 H 5,02 at 8.36 N S Of 12.76 Cl 14,11

Found (%): C 52,20 H 5,03 of 8.37 N S 12,43 Cl 13,91

Example 89

Synthesis of 5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl - 2-(N-methylthiocarbamate)aminomethyl-1H-imidazole (Compound 1-89)

Compound 1-89 was obtained by the method described in example 44 synthesis of Compound 1-44 using 30A as the source connection. So pl. 188-190oC.

1H-NMR (CDCl3-TMS) million D.: 1,21 (d, J= 7,0 Hz, 6H), 3.04 from (d, J= 4,8 Hz, 3H), 3,13 (Sept., 1H), to 3.58 (s, 3H), around 4.85 (d, 2H), PC 6.82 (d, J= 1.6 Hz, 2H), 7,14 (t, J= 1.6 Hz, 1H).

Elemental analysis (C16H20Cl2N4 the EP 90

Synthesis of 5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-2 - freedomites-1H-imidazole (Compound 1-90)

The connection between 1 and 90 were obtained by the method described in example 41 synthesis of Compounds 1-41 using the Connection 1-85 as source material. The physical properties of the intermediate connection; so pl. 163-165oC.

1H-NMR (CDCl3-TMS) million D.; of 1.28 (d, J=7.2 Hz, 6H), 3,13 (Sept., 1H) and 3.59 (s, 3H), 4.72 in (d, J= 5.8 Hz, 2H), PC 6.82 (d, J= 1.8 Hz, 2H), 7,15 (t, J= 1.8 Hz, 1H), 8,53 (width,1H), 8,65 (width, 1H).

The physical properties of the Compound 1-90: so pl. 192-194oC.

1H-NMR (CDCl3-TMS) million D.: 1,21 (d, J= 7.2 Hz, 6H), 3,11 (Sept., 1H), 3,53 (s, 3H), 4,50 (d, J= 5.8 Hz, 2H), 4,85 (width, 2H), 6,32 (width, 1H), 6,80 (d, J= 1.8 Hz, 2H), 7,26 (t, J= 1.8 Hz, 1H).

Elemental analysis (C15H18Cl2N4OS)

Calculated (%): C 48,26 H a 4.86 N 15,01 S 8,59 Cl 18,99

Found (%): C 48,21 H 4,91 N 14,85 S 8,51 Cl 18,85.

Example 91

Synthesis of 5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-2 - methoxycarbonylaminophenyl-1H-imidazole (Compound 1-91)

Compound 1-91 was obtained by the method described in example 84 synthesis of Compound 1-84 using 30A as the source connection. So pl. 138-139oC.

1H-NMR (CDCl3-TMS) million D.: of 1.23 (d, J= 7,0 Hz, 6H), 3,10 (Sept., 1H), 3,54 (C. 3H), 3,71 (s, 3H), 4,50 (d, J= 5.6 Hz, 2H), 5,75 /SUB>S)

Calculated (%): C 49,49 H 4,93 N 10,82 S compared to 8.26 Cl 18,26

Found (%): C 49,18 H 4,92 N 10,53 S 8,27 Cl 18,64.

Example 92

Synthesis of 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl - 1-(pyridine-3-yl)methyl-1H-imidazole (Compound 1-92)

The compound 5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p - methoxybenzyloxy)-1-(pyridine-3-yl)methyl-1H-imidazole (17ab) was obtained from compound (16b) by the method described in Comparative example 2 for the synthesis of (17b). An oily substance.

1H-NMR (CDCl3-TMS) million D.: of 1.27 (d, J= 7,0 Hz, 6H), 3,10 (Sept., 1H), 3,79 (s, 3H), 4,48 (s, 2H), with 4.64 (s, 2H), 5,16 (s, 2H), is 6.61 (d, J= 1.2 Hz, 2H), at 6.84 (d, J= 8.6 Hz, 2H), 7,02~7,07 (m, 2H), 7,16~7,26 (m, 5H), to 8.34 (width, 2H).

The compound [5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-3-yl) methyl-1H-imidazol-2-yl] methanol (12ad) was obtained from (17ad) by the method described in Comparative example 2 for the synthesis of Compounds 1-8. So pl. 136-139oC.

1H-NMR (CDCl3-TMS) million D.; to 1.23 (d, J= 6.9 Hz, 6H), 3.15 in (Sept., 1H), 3,81 (s, 3H), 4,39 (s, 3H), 4,80 (s, 2H), 5,27 (s, 2H), of 6.20 (s, 2H), to 6.88 (d, J= 8.7 Hz), 7,02 (s, 1H), 7,10-7,24 (m, 1H), 7,35-7,38 (m, 1H), 8,40-8,42 (m, 1H).

Elemental analysis (C19H19Cl2N3OS)

Calculated (%): C 55,89 H 4,69 H 10,29's A 7.85 Cl 17,36

Found (%); C 55,78 H 4,79 N 10,20 S 7,88 Cl 17,60

2-(N-Chloroacetanilide)methyl-5-(3,5-dichlorophenylthio)-4 - isoprene (22). An oily substance.

1H-NMR (CDCl3-TMS) million D.: 1,31 (d, J= 8,1 Hz, 6H), 3,17 (Sept., 1H), 4,35 (s, 2H), to 5.03 (s, 2H), 5,33 (s, 2H), of 6.68 (s, 2H), was 7.08 (s, 1H), 7,25~ 7,29 (m, 2H), 8.34 per~8,35 (m, 1H), 8,46-8,48 (m, 1H).

Compound 1-92 was obtained by the method described in example 45 to obtain Compounds 1-45. So pl. 152-155oC.

1H-NMR (CDCl3-TMS) million D.: of 1.28 (d, J= 7,0 Hz, 6H), 3.15 in (Sept., 1H), 4,63 (Shir. , 2H), 5,23 (s, 2H), 5,24 (s, 2H), only 6.64 (d, J= 1.6 Hz, 2H),? 7.04 baby mortality (d, J= 16 Hz, 1H),? 7.04 baby mortality-7,26 (m, 4H), 8,30 (d, J= 0.8 Hz, 1H), to 8.41, 8,42 (DD, J= 4,6 Hz, 1.2 Hz, 1H).

Elemental analysis (C20H20Cl2N4O2S)

Calculated (%); C 53,22 H 4,47 N 12,41 S 7,00 Cl 15,71

Found (%): C 52,96 To 4.52 H N S 12,13 7,00 Cl 15,80.

Example 93

Synthesis of 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-4 - isopropyl-1-(pyridine-2-yl)methyl-1H-imidazole (Compound 1-93)

2-Benzoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1- (pyridine-2-yl)methyl-1H-imidazole (AE) was obtained from compound (16A) by the method described in Comparative example 1 to obtain compound (17A). An oily substance.

1H-NMR (CDCl3-TMS) million D.; of 1.28 (d, J=7 Hz, 6H), 3,12 (Sept., 1H), a 4.53 (s, 2H), of 4.77 (s, 2H), 5,32 (s, 2H), of 6.31 (d, J= 1.8 Hz, 2H), 6.73 x (d, J= 7.8 Hz, 1H), 6,94 (t, J= 1.8 Hz, 1H), 6,95~7,03 (m, 2H), 7,27 was 7.36 (m, 6H), 8,40~ 8,43 (m, 1H).

[5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(p is for obtaining compounds (12A). So pl. 145-146oC.

1H-NMR (CDCl3-TMS) million D.: 1,22 (d, J= 7,0 Hz, 6H), of 3.07 (Sept., 1H), 4,91 (d, J= 5.8 Hz, 2H), of 5.34 (t, J= 5.8 Hz, 1H), 6,41 (d, J=2 Hz, 2H), 6,91 (t, J= 2 Hz, 1H), 7,05~7,13 (m, 2H), 7,32~7,37 (m, 1H), 8,43~of 8.47 (m, 1H).

Elemental analysis (C19H19Cl2N3OS)

Calculated (%): C 55,89 H 4,69 N 10,29's A 7.85 Cl 17,36

Found (%): C 55,83 H 4,82 N S 10,11 7,78 Cl 17,08.

The target Compound 1-93 received from connections (AE) by the method described in example 45 to obtain Compounds 1-45. So pl. 127-130oC.

1H-NMR (CDCl3-TMS) million D.: of 1.28 (d, J= 6.9 Hz, 6H), 3,13 (Sept., 1H), 4,62 (Shir. , 2H), 5,32 (s, 2H), are 5.36 (s, 2H), 6,62 (s, 2H), 6,78 (d, J= 7.8 Hz, 1H), 6,95 (s, 1H), 7,02 ~7,07 (m, 1H), 7,38~7,44 (m, 1H), 8,43~8,46 (m, 1H).

Elemental analysis (C20H20Cl2N4ABOUT2S)

Calculated (%): C 53,22 H 4,47 N 12,41 S 7,00 Cl 15,71

Found (%): C 53,23 H 4,51 N 12,36 S 6,98 Cl 15,45.

Example 93'

Synthesis of 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl - 1-(pyridine-4-yl)methyl-1H-imidazole (Compound 1-93')

2-Benzoyloxymethyl-5-(3,5-Dichlorophenylthio)-4-isopropyl-1- (pyridine-4-yl)methyl-1H-imidazole (17af) was obtained from compound (16A) by the method described in Comparative example 1 to obtain (17A).

[5-(3,5-Dichlorophenylthio)-4-isopropyl-1-(pyridine-4-yl)methyl - 1H-imidazol-2-yl]methanol (12af) the least 1. So pl. 137-139oC.

1H-NMR (CDCl3-TMS) million D.; 1.27mm (d, J = 7,0 Hz, 6H), 3,12 (Sept., 1H), and 4.75 (s, 2H), 5,26 (s, 2H), 6,66 (d, J= 2 Hz, 2H), 6.87 in (DD, J = 1.6 Hz, 6 Hz, H), 7,05 (t, J= 2.4 Hz, H), 8,44 (DD, J = 1.6 Hz, 6 Hz, H).

Elemental analysis (C19H19Cl2N3OS)

Calculated (%): C 55,89 H 4,69 N 10,29's A 7.85 Cl 17,36

Found (%): C 55,92 H 4,74 N 10,24 S Of 7.64 Cl 17,09.

2HCl salt of compound (12af): so pl. 223-235oC (decomposition).

2-(N-(chloroacetyl)carbanilate)methyl-5-(3,5-dichlorophenylthio)-4 - isopropyl-1-(pyridine-4-yl)methyl-1H-imidazole (22af) was obtained from (12af) method used to obtain (22) in example 45. An oily substance.

1H-NMR (CDCl3-TMS) million D.: 1,32 (d, J= 7,0 Hz, 6H), 3,17 (Sept., 1H), 4,30 (s, 2H), 5,28 (s, 2H), 5,31 (s, 2H), of 6.71 (d, J= 1.4 Hz, 2H) PC 6.82 (d, J= 5.8 Hz, 2H), 7,05 (t, J= 1.4 Hz, 1H), 8,20 (width, 1H), 8,49 (d, J= 5.4 Hz, 2H).

The target compound 1-93' was obtained from the compound (12af) by the method described in example 45 to obtain Compounds 1-45. So pl. 88oC (decomposition).

1H-NMR (CDCl3-TMS) million D.: 1,32 (d, J= 6.9 Hz, 6H), 3,17 (Sept., 1H), 4.53-in (W, 2H), total of 5.21 (s, 2H), 5,27 (s, 2H), 6,69 (d, J=1.6 Hz, 2H), PC 6.82 (d, J= 5,2 Hz, 2H), 7,06 (t, J= 1.6 Hz, 1H), 8,46 (width, 2H).

Elemental analysis of C20H20Cl2N4O2S0,5H2O)

Calculated (%): C 52,16 H Br4.61 N 12,17 S Of 6.96 Cl 15,42<>Example 94

Synthesis of 2-aminomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1- (pyridine-3-yl)methyl-1H-imidazole (Compound 1-94)

2-Azidomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-3 - yl)methyl-1H-imidazole (29ad) was obtained from compound (e) by the method described in example 66 to obtain the compound (29A). An oily substance.

1H-NMR (CDCl3-TMS) million D.: of 1.28 (d, J= 6.8 Hz, 6H), 3.15 in (Sept., 1H), 4,50 (s, 2H), 5,20 (s, 2H), 6,65 (d, J=1.8 Hz, 2H), 7,06 (t, J= 1.8 Hz, 1H), 7,06~7,27 (m, 2H), at 8.36 (W, 1H), 8,45 (width, 1H).

Compound 1-94 received from (29ad) by the method described in example 66 to obtain the connection (30A). So pl. 99-103oC.

1H-NMR (CDCl3-TMS) million D.: of 1.28 (d, J=6.6 Hz, 6H), 3,14 (Sept., 1H), 3,99 (s, 2H), 5,26 (s, 2H). to 6.67 (s, 2H),? 7.04 baby mortality (s, 1H), 7,11~7,20 (m, 1H), 7,25~7,35 (m, 1H), of 8.37 (d, J= 0.9 Hz, 1H), 8,43 (d, J= 6,6 Hz, 1H).

Elemental analysis (C19H20Cl2N4OS 0,2 H2O)

Calculated (%): C 55,53 H 5,00 N 13,63 S 7,80

Found (%): C 55,46 H 4,96 N 13,57 S 7,60.

Example 95

Synthesis of 2-aminomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1- (pyridine-2-yl)methyl-1H-imidazole (Compound 1-95)

2-Azidomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine - 2-yl)methyl-1H-imidazole (AE) was obtained from compound (e) by the method described in example 66 to obtain the compound (29A). Oil is(s, 2H), 6,83 (d, J= 7.8 Hz, 1H), 6,95 (s, 1H), 7,06~7,10 (m, 1H), 7,39~ 7,45 (m, 1H), 8,46~8,49 (m, 1H).

IR (film) 2100 cm-1< / BR>
Connection 1-95 received from (e) by the method described in example 66 to obtain (30A), Oily substance.

1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J= 6.9 Hz, 6H), 3,12 (Sept., 1H), 4,01 (s, 2H), of 5.05 (s, 2H), 6,60 (s, 2H), 6,85 (d, J= 7.8 Hz, 1H), 6,95 (s, 1H), 7,02~7,10 (m, 1H), 7,22~ 7,28 (m, 1H), 7,38~the 7.43 (m, 1H).

Example 95

Synthesis of 2-aminomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1 - (- perigee-4-yl)methyl-1H-imidazole (Compound 1-95')

2-Azidomethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-4 - yl)methyl-1H-imidazole (29af) was obtained from compound (12af) by the method described in example 66 to obtain (29A). An oily substance.

1H-NMR (CDCl3-TMS) million D.: 1,31 (d, J = 6.8 Hz, 6H), 3,18 (Sept., 1H), 4,47 (s, 2H), 5,20 (s, 2H), 6,69 (d, J=1.8 Hz, 2H), PC 6.82 (d, J= 5.6 Hz. 2H), 7,06 (t, J= 1.8 Hz, 1H), of 8.47 (width, 2H).

IR (film) 2080 cm-1< / BR>
Connection 1-95' received from (29af) by the method described in example 66 to obtain the connection (30A). An oily substance.

1H-NMR (CDCl3-TMS) million D.: of 1.30 (d, J=8,2 Hz, 6H), and 3.16 (Sept., 1H), 3,95 (s, 2H, in), 5.25 (s, 2H), of 6.71 (d, J= 1.2 Hz, 2H), 6,83 (d, J= 4,8 Hz, 2H),? 7.04 baby mortality (t, J= 1.2 Hz, 1H), 8,42~8,48 (m, 1H).

3HCl salt Compound 1-95': So pl. 252-260oC (decomposition)

the>/BR>Found (%); C 42,07 H 4,67 N 10,55 Of 5.92 S Cl 32,51.

Example 96

Synthesis of methyl-2-1,2-dimethyl-5-(3,5-dimethylphenyl)-1H - imidazol-4-yl] propionate (Compound 1-96)

A solution of 7.0 g (3.2 mmol) of 5-(3,5-dimethylphenyl)-2-methyl - 1H-imidazole (5b) in 37% aqueous formaldehyde (20 ml) was heated at 120oC in a sealed tube for 15 hours. The reaction mixture was dissolved in methanol/methylene chloride, and the aqueous layer was separated. The organic layer was dried with sodium sulfate, and the solvent is kept at reduced pressure. The residue was purified by chromatography on silica gel (methanol:ethyl acetate to 2:98), and the crude product was washed with isopropyl ether, which was obtained 1.7 g of [5-(3,5-dimethylphenyl)- 2-methyl-1H-imidazol-4-yl] methanol (41d) (yield 21%). So pl. 199-201oC.

1H-NMR (DMSO-d6-TMS) million D.: 2,17 (s, 6H), and 2.27 (s, 3H), to 4.41 (m, 2H), 5,09 (width, 1H), 6,74 (K, 3H), 12,16 (width, 1H).

In anhydrous methylene chloride (85 ml) was dissolved 1.7 g (6.8 mmol) [5-(3,5-dimethylphenyl)-2-methyl-1H-imidazol-4-yl] methanol (41d), and then was added 2.10 g (to 20.8 mmol) of triethylamine. Then to this solution, stirring while cooling with ice, drop by drop added acetylchloride. The resulting mixture was stirred at the same temperature for 30 minutes, then add the ionic mixture was added for neutralization with saturated aqueous sodium bicarbonate solution and was extracted with methylene chloride. The extract was washed with water and dried with sodium sulfate. The solvent is kept at reduced pressure, and the residue was purified by chromatography on silica gel (ethyl acetate), resulting in a received 1.55 g of [5-(3,5-dimethylphenyl)- 2-methyl-1H-imidazol-4-yl]methyl acetate (41b) in the form of oily substance (yield 78%)

1H-NMR (CDCl3-TMS) million D.: 2,05 (s, 6H), of 2.21 (s, 3H), 2,39 (s, 3H), 5,11 (s, 2H), 6.75 in (s, 3H), 9,81 (width, 1H).

In 26 ml of anhydrous dimethylformamide was dissolved 1,33 g (4.6 mmol) [5-(3,5-dimethylphenyl)-2-methyl-1H-imidazol-4-yl] methyl acetate (41b), and then was added 1.28 g (9.3 mmol) of anhydrous potassium carbonate and 715 mg (5.0 mmol) under the conditions, after which the mixture is stirred at room temperature for 2 hours. Then to the reaction mixture were added ice water and was extracted with diethyl ether, and the organic layer was washed with water and dried with sodium sulfate. The solvent is kept under reduced pressure, and the obtained crude product was fractionally using chromatography on silica gel (ethyl acetate), resulting in a received 510 ml [5-(1,2-dimethyl - 3,5-dimethylphenyl)imidazol-4-yl] methyl acetate (42A) in the form of oily substance (yield 37%).

1H-NMR (CDCl3-TMS) million D.: 2,05 (s, 6H), of 2.23 (s, 3H), of 2.46 (s, 3H), 3.46 in (with, is ethylvanillin)-1H-imidazol-4-yl] methyl acetate (42A), and then was added to 4.9 ml of 1 H a solution of sodium methylate at room temperature, and the mixture was stirred for 30 minutes. Then to the reaction mixture were added water and the mixture was extracted with methylene chloride, and the organic layer was washed with water and dried with sodium sulfate. The solvent was concentrated under reduced pressure, and the residue was recrystallized from a mixture of ethyl acetate and isopropyl ether, resulting in the received 398 mg [1,2-dimethyl-5-(3,5-dimethylphenyl)-1H-imidazol-4-yl] methanol (42b) (yield 93%). So pl. 198-199oC.

1H-NMR (CDCl3-TMS) million D.: of 2.23 (s, 6H), 2.40 a (width, 1H), 2,46 (s, 3H), of 3.45 (s, 3H), 4,47 (s, 2H), only 6.64 (s, 2H), 6,78 (s, 1H).

To 1.9 ml of thionyl chloride was added 370 mg (1.4 mmol) of [1,2-dimethyl-5-(3,5-dimethylphenyl)-1H-imidazol-4-yl] methanol (42b), and the resulting mixture was heated at 70oC for 3 hours. Then the reaction mixture was concentrated under reduced pressure. Then to the reaction mixture was added ice water, and then to neutralize - saturated aqueous sodium bicarbonate solution and was extracted with diethyl ether. The organic layer was washed with water and dried with sodium sulfate, and the solvent is kept at reduced pressure. The residue was purified by chromatography the ash (42c) in the form of oily substance (yield 73%).

1H-NMR (CDCl3-TMS) million D.: of 2.25 (s, 6H), 2,48 (s, 3H), 3.46 in (s, 3H), 4,71 (s, 2H), of 6.71 (s, 2H), for 6.81 (s, 1H).

5.6 ml of anhydrous dimethylformamide was dissolved 280 mg (1.0 mmol) 4-chloromethyl-1,2-dimethyl-5-(3,5-dimethylphenyl)-1H-imidazole (42s). Then was added 98 mg (1.5 mmol) of potassium cyanide, and the mixture was heated at 50oC for 5 hours. Then to the reaction mixture was added ice water, the extract was washed with water and dried with sodium sulfate. The solvent is kept under reduced pressure, and the residue was purified by chromatography on silica gel (ethyl acetate), resulting in a received 114 mg [1,2-dimethyl-5- (3,5-dimethylphenyl)-1H-imidazol-4-yl]acetonitrile (42d) (yield 42%). Etc., 81-82oC.

1H-NMR (CDCl3-TMS) million D.: 2,24 (s, 6H), 2,47 (s,3H), 3,47 (s, 3H), 3,76 (s, 2H), 6,60 (s, 2H), 6,80 (s, 1H).

In anhydrous tetrahydrofuran (5 ml) was dissolved 49 mg (0.48 mmol) of Diisopropylamine, and the solution was cooled to 0oC. To this solution in a stream of nitrogen was added 0.3 ml of 1.62 M hexane solution of n-utility, and the resulting mixture stirred for 10 minutes. Then the mixture was cooled to -78oC and was added 85 mg (0.31 mmol) of [1,2-dimethyl-5-(3,5-dimethylphenyl) imidazol-4-yl]acetonitrile (42d), after which the mixture is stirred for 15 minutes. To polucen and the mixture is stirred for 30 minutes at -78oC. the Reaction mixture was poured into ice water, was extracted with diethyl ether, and the extract was washed with water and dried with sodium sulfate. The solvent is kept under reduced pressure, and the residue was purified by chromatography on silica gel (ethyl acetate), resulting in a received 51 mg of 2-[1,2-dimethyl-5-(3,5-dimethylphenyl)-1H-imidazol-4 - yl]propionitrile (43A) in the form of oily substance (yield 57%)

1H-NMR (CDCl3-TMS) million D.: 1,63 (d, J= 7.2 Hz, 3H), 2,24 (s, 6H), 2,48 (s, 3H), 3.46 in (s, 3H), 4,15 (sq, J= 7.2 Hz, 1H), 6,60 (s, 2H), 6,80 (s, 1H).

In 5 ml of a mixture methanol/diethyl ether (about 1/3./vol.%), rich chlorocarbon, was dissolved 60 mg (0.21 mmol) 2-[1,2-dimethyl-5-(3,5-dimethylphenyl)-1H-imidazol-4-yl] propionitrile (43A), and the resulting mixture was left for 23 hours at 4oC. Then the reaction mixture was added 2 ml of methanol and 0.3 ml of water, and the mixture was stirred for 4 hours at room temperature. Then the reaction mixture was added to saturated aqueous sodium bicarbonate solution and was extracted with methylene chloride. The organic layer was washed with water and dried with sodium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel (ethyl acetate), in CDCl3-TMS) million D.: 1,51 (d, J = 7,4 Hz, 3H), of 2.23 (s, 6H), of 2.45 (s, 3H), 3.43 points (s, 3H) and 3.59 (s, 3H), 4,01 (sq, J= 7,4 Hz, 1H), 6,63 (s, 2H), 6,77 (s, 1H).

Example 97

Synthesis of 2-[5-(3-chlorophenylthio)-1,2-dimethyl-1H-imidazol-4-yl] propionitrile (Compound 1-97) [5-(3-Chlorophenylthio)-1,2-dimethyl-1H - imidazol-4-yl]acetonitrile (42f) was obtained from [5-(3-chlorophenylthio)-1,2 - dimethyl-1H-imidazol-4-yl] methanol (e) by the method described in example 96 to obtain the Compound 42d. So pl. 90-91oC.

1H-NMR (CDCl3-TMS) million D.: 2,48 (s, 3H), 3,47 (s, 3H), 3,76 (s, 2H), 6,82~7,27 (m, 4H).

Compound 1-97 was obtained by the method described in example 96 synthesis of Compound 1-96.

1H-NMR (CDCl3-TMS) million D.: 1,64 (d, J= 6.8 Hz, 3H), 2.49 USD (s, 3H), 3,47 (s, 3H), 4,13 (sq, J = 6,8 Hz, 1H), for 6.81~7,27 (m, 4H).

Example 98

Synthesis of 2-[2-carbamoyloxymethyl-5-(3-chlorophenylthio)-1-methyl-1H - imidazol-4-yl]propiononitrile (Compound 1-98)

1-Benzoyloxymethyl-2-imidazolecarboxaldehyde (44) was obtained as an oily product from 1-benzoyloxymethyl-1H-imidazole by the method described in example 6 for the synthesis of Compounds 1-6. Yield 95%.

1H-NMR (CDCl3-TMS) million D.: 4,55 (s, 2H), by 5.87 (s, 2H), 7,26 ~ 7,37 (m, 7H), 9,86 (s, 1H).

In a manner analogous to the method described in example 8 for the synthesis of Compounds 1-8, received (1-beside (44) and was purified by chromatography on silica gel (ethyl acetate : methanol = 19 : 1). Yield 53%.

1H-NMR (CDCl3-TMS) million D.: of 4.49 (s, 2H), 4,71 (s, 2H), 5,10 (width, 1H), 5,44 (s, 2H), 6,92 (m, 1H), 6,99 (m, 1H), 7,33 (m, 5H).

In a solution of 29.5 g (135 mmol) (1-benzoyloxymethyl-1H-imidazol-2-yl)methanol in anhydrous methylene chloride (295 ml) was added 11.1 g (163 mmol) of imidazole, and then cooling with ice, drop by drop was added 24.4 g (162 mmol) of tert-butylmethacrylate. After complete addition, the reaction mixture is stirred for 30 minutes at room temperature. Then to the reaction mixture was added ice water, the resulting mixture was extracted with methylene chloride, and the extract was washed with water and dried with sodium sulfate. The solvent is kept under reduced pressure and got to 43.0 g of 1-benzoyloxymethyl-2-t-butyldimethylsilyloxy (44') in the form of an oily product (yield 96%).

1H-NMR (CDCl3-TMS) million D.: of 0.05 (s, 6H), 0,81 (s, 9H), 4,43 (s, 2H), amounts to 4.76 (s, 2H), 5,42 (s, 2H), 6,92 ~ 7,30 (m, 7H).

A solution of 29.5 g (88.7 mmol) 1-benzoyloxymethyl-2-t-butyldimethylsilyloxy-1H-imidazole (44') in anhydrous tetrahydrofuran was cooled to -78oC, and then the flow of nitrogen drop was added 76 ml of 1.66 M hexane solution of n-utillity. The resulting mixture was stirred 5 minutes at the same temperature, and then gradually the Reaction mixture was poured into water with ice, was extracted with diethyl ether, and the organic layer was washed with water and dried with sodium sulfate. The solvent is kept under reduced pressure, and the residue was purified by chromatography on silica gel (ethyl acetate: n-hexane = 1:2), resulting received a 21.5 g of 1-benzoyloxymethyl-2-t - butyldimethylsilyloxy-5-(3-chlorophenylthio)imidazole (45) in the form of an oily product (yield 51%).

1H-NMR (CDCl3-TMS) million D.; and 0.09 (s, 6H), of 0.87 (s, 9H), 4,39 (s, 2H), a 4.86 (s, 2H), 5,51 (s, 2H), 6.90 to~of 7.36 (m, 10H).

To a solution of 1-benzoyloxymethyl-2-t-butyldimethylsilyloxy-5- (3-chlorophenylthio)imidazole (45) in nitromethane (108 ml) was added to 14.7 g (137 mmol) of anisole, and then at a temperature lower than the 30oC was gradually added to 18.1 g (136 mmol) of anhydrous aluminium chloride. After complete addition, the mixture is stirred at room temperature for 15 minutes. The reaction mixture was cooled, then added water and saturated aqueous sodium bicarbonate solution for alkalizing. Then to the mixture was added ethyl acetate, and the resulting mixture was filtered to separate on Hiflow Super Cell. The organic layer was washed with water, dried with sodium sulfate, and the solvent was concentrated under reduced pressure. The residue was purified with pometia)-1H-imidazol-2-yl] methanol as an oily product (yield 87%).

1H-NMR (CDCl3-TMS) million D.; 4,00 (width, 2H), with 4.64 (s, 2H), 7.03 is~7,28 (m, 5H).

2-t-Butylbenzamidoxime-5-(3-chlorophenylthio)imidazole was obtained from [5-(3-chlorophenylthio)-1H-imidazol-2-yl]methanol in the same manner, which has received the above-mentioned 1-benzoyloxymethyl-2-t - butyldimethylsilyloxy (44'). (Yield 60%). So pl. 107 - 108oC.

1H-NMR (CDCl3-TMS) million D.; 0,03 (s, 6H), of 0.82 (s, 9H), 4,74 (s, 2H), 7,00 (m, 4H), 7,20 (s, 1H), 9,50 (width, 1H).

An aqueous solution of 2.0 g (5.6 mmol) of 2-t-butyldimethylsilyloxy - 5-(3-chlorophenylthio)-1H-imidazole (45') of 37% formalin (10 ml) was heated at 120oC in a sealed tube for 10 hours. Then the reaction mixture was washed from the tube with methanol, dried with sodium sulfate, and the solvent is kept at reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate: n-hexane 1:9), the crude product was washed with n-hexane and filtered, resulting in a received 716 mg of [2-t - butyldimethylsilyloxy-5-(3-chlorophenylthio)-1H-imidazol-4-yl] methanol (46) (yield 33%). So pl. 136-137oC.

1H-NMR (CDCl3-TMS) million D.: of 0.08 (s, 6H), to 0.89 (s, 9H), to 4.46 (d, J= 5.0 Hz, 2H), to 4.62 (s, 2H), 5,23 (t, J=5.0 Hz, 1H), 7,05~7,30 (m, 4H), 12,59 (width, 1H).

In a solution of 700 mg (1.8 mmol) [2-t-buildmode) of triethylamine, and then, stirring with ice cooling for one drop was added to 1.00 g (12.8 mmol) of acetylchloride. The reaction mixture is stirred for 15 minutes at room temperature, after which was added for neutralization to a cooled saturated aqueous sodium bicarbonate solution, and was extracted with methylene chloride. The organic layer was washed with water and dried with sodium sulfate. The solvent is kept at reduced pressure. The residue was dissolved in 5 ml of methanol, to which was added 5 ml of 50% aqueous acetic acid, and the mixture was stirred at room temperature for 1 hour. Then to the reaction mixture were added for neutralization with saturated aqueous sodium bicarbonate solution and was extracted with methylene chloride. The organic layer was washed with water and dried with sodium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel (ethyl acetate:n-hexane = 1:2), resulting in a received 602 mg of [2-t - butyldimethylsilyloxy-5-(3-chlorophenylthio)-1H-imidazol-4-yl] acetate as an oily product (yield 78%).

1H-NMR (CDCl3-TMS) million D.; 0,13 (s, 6H), of 0.95 (s, 9H), of 2.08 (s, 3H), 4,80 (s, 2H), 5,16 (s, 2H), 7,10 (m, 4H), 9,83 (width, 1H).

In 12 ml betw the l-4-yl]acetate, and then was added anhydrous potassium carbonate (2.8 mmol). After this was added 240 mg (1.7 mmol) under the conditions, and the reaction mixture is stirred for 1 hour at room temperature. To the reaction mixture was added ice water, after which the mixture was extracted with diethyl ether, and the organic layer was washed with water and dried with sodium sulfate. The solvent is kept under reduced pressure, and the residue was purified by chromatography on silica gel (ethyl acetate:n-hexane = 1:2), resulting in a received 288 mg of [2-t - butyldimethylsilyloxy-5-(3-chlorophenylthio)-1-methyl-1H-imidazol - 4-yl]methyl acetate (47) in the form of an oily product. (Yield 46%).

1H-NMR (CDCl3-TMS) million D.: of 0.08 (s, 6H), of 0.87 (s, 9H), 2,02 (s, 3H), of 3.60 (s, 3H), 4,82 (s, 2H), 5,13 (s, 2H), 6.90 to~to 7.18 (m, 4H).

[2-t-Butyldimethylsilyloxy-5-(3-dichlorophenylthio)-1-methyl - 1H-imidazol-4-yl]methanol was obtained from the compound (47) by the method described in example 96 to obtain (42b).

So pl. 111-112oC.

1H-NMR (CDCl3-TMS) million D.: 0,72 (s, 6H), of 0.87 (s, 9H), 3,30 (width, 1H) and 3.59 (s, 3H), 4,68 (width, 2H), 4,80 (s, 2H), 6,88~7,17 (m, 4H).

2-t-Butyldimethylsilyloxy-4-chloromethyl-5-(3-chlorophenylthio)- 1-methyl-1H-imidazole was obtained from [2-t-butyldimethylsilyloxy-5- (3-chlorophenylthio)-1-isH-NMR (CDCl3-TMS) million D.: of 0.07 (s, 6H), of 0.87 (s, 9H), 3,30, (W.,1H), to 3.58 (s, 3H), of 4.67 (s, 2H), to 4.81 (s, 2H), 6.90 to~7,22 (m, 4H).

[2-t-Butyldimethylsilyloxy-5-(3-chlorophenylthio)-1 - methyl-1H-imidazol-4-yl] acetonitrile (48) was obtained from 2-t - butyldimethylsilyloxy-4-chloromethyl-5-(3-chlorophenylthio)-1 - methylimidazole by the method described in example 96 to obtain (42d), oily substance.

1H-NMR (CDCl3-TMS) million D.: 0,09 (s, 6H), to 0.88 (s, 9H), of 3.60 (s, 3H), of 3.77 (s, 2H), to 4.81 (s, 2H), 6,80~7,22 (m, 4H).

In anhydrous tetrahydrofuran (5 ml) was dissolved 87 mg (0.86 mmol) of Diisopropylamine, and the solution was cooled to 0oC. and Then in an atmosphere of gaseous nitrogen was added 0.5 ml 1,71 M hexane solution of n-utility, and the resulting mixture stirred for 10 minutes. After that, the mixture was cooled to -78oC, and then added 200 mg of [2-t-butyldimethylsilyloxy-5-(3-chlorophenylthio)-1-methyl-1H - imidazol-4-yl]-acetonitrile (48), and the mixture is stirred for 25 minutes. Then one drop was added 154 mg (0.86 mmol) of triamide hexamethylphosphoric acid and 122 mg (0.86 mmol) under the conditions, and the resulting mixture stirred at -78oC for 10 minutes. The reaction mixture was poured into ice water, was extracted with diethyl ether, and the extract was washed with water and drained Alfie on silica gel (ethyl acetate: n-hexane = 1:2). From the first fraction received 40 mg of 2-(2-t-butyldimethylsilyloxy-5-(3-chlorophenylthio)-1-methyl-1H - imidazol-4-yl)-2-methylpropionitrile (49') in the form of an oily product (yield 19%). And from the subsequent fractions were obtained 70 mg of 2-(2-t-butyldimethylsilyloxy-5-(3-chlorophenylthio)-1-methyl-1H - imidazol-4-yl)- propionitrile (50') in the form of an oily product (yield 34%).

49'1H-NMR (CDCl3-TMS) million D.: of 0.08 (s, 6H), to 0.88 (s, 9H), to 1.76 (s, 6H), of 3.56 (s, 3H), 4,79 (s, 2H), 6,80~7,22 (m, 4H).

50'1H-NMR (CDCl3-TMS) million D.: of 0.08 (s, 6H), of 0.87 (s, 9H), and 1.63 (d, J= 7,4 Hz, 3H), of 3.60 (s, 3H), 4,12 (sq, J=7,4 Hz, 1H), 4,82 (s, 2H), 6,80~7,22 (m, 4H).

In anhydrous tetrahydrofuran (2 ml) was dissolved 70 mg of 2-(2 - butyldimethylsilyloxy-5-(3-chlorophenylthio)-1-methyl-1H-imidazol - 4-yl)propiononitrile (50'), and then was added 0.33 ml of a 1M solution of tetrabutylammonium fluoride-tetrahydrofuran, and the reaction mixture stirred 10 minutes at room temperature. To the reaction mixture was added water, the mixture was extracted with methylene chloride, the organic layer was washed with water and dried with sodium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by chromatography on silica gel (ethyl acetate), resulting in received 50 mg of 2-[5-(3-chlorophenylthio)-2-hydroxymet the (CDCl3-TMS) million D.; to 1.61 (d, J= 7,4 Hz), 3,60 (s, 3H), 4,13 (sq, J= 7,4 Hz, 1H), 4,20 (width, 1H), 4,79 (s, 2H), 6,79~7,25 (m, 4H).

2-[5-(3-Chlorophenylthio)-2-hydroxymethyl-1-Mei-4-yl] -2 - methylpropionitrile (49) was obtained from (49') in the same way, which was obtained 2-[5-(3-chlorophenylthio)-2-hydroxymethyl-1-Mei-4-yl] propiononitrile (50). The oily product.

1H-NMR (CDCl3-TMS) million D.; to 1.76 (s, 6H), 3,24 (m, 1H), of 3.56 (s, 3H), amounts to 4.76 (d, J= 5.4 Hz, 2H), 6,80~7,22 (m, 4H).

Compound 1-98 was obtained from 2-[5-(3-chlorophenylthio)-2 - hydroxymethyl-1-methyl-1H-imidazol-4-yl] propiononitrile (50) in the same way, which received the Connection 1-59 in example 59. The oily product.

1H-NMR (CDCl3-TMS) million D.: 1,63 (d, J=7.2 Hz, 3H), of 3.60 (s, 3H), 4,15 (sq, J= 7.2 Hz, 1H), 4,82 (width, 2H), 5,23 (s, 2H), 6,80~7,25 (m, 4H).

Example 99

Synthesis of 2-[5-(3-chlorophenylthio)-1,2-dimethyl-1H-imidazol-4-yl] propionic acid (Compound 1-99)

A solution of 30 mg of 2-[5-(3-chlorophenylthio)-1,2-dimethyl-1H-imidazol-4 - yl]propiononitrile (52) in 3 ml 6 H hydrochloric acid was left for reaction at 110oC. the Mixture was concentrated under reduced pressure, podslushivaet 28% ammonia water, and then acidified with acetic acid. The aqueous solution was loaded on a column of 25 g of MCl-GEL (CHP20P 75-150 MK), and suirable purified water, the mg of target compound (Compound 1-99) as an oily product (yield 78%).

1H-NMR (CDCl3-TMS) million D.: 1,49 (d, J= 7,4 Hz, 3H), 2,48 (s, 3H), 3.46 in (s, 3H), 3,95 (sq, J= 7,4 Hz, 1H), 6,84~7,20 (m, 5H).

Example 100

Synthesis of 5-(3,5-dichlorobenzyl)-1,2-dimethyl-4-isopropyl-1H - imidazole (Compound 1-100)

In 20 ml of anhydrous acetone was dissolved 930 mg (3.3 mmol) of 5-(3,5-dichlorobenzyl)-4-isopropyl-2-methyl-1H-imidazole (54), and then was added 1.4 g (10.1 mmol) of anhydrous potassium carbonate, and the mixture was stirred at room temperature. After 5 minutes was added 225 μl (3.6 mmol) under the conditions at room temperature, and the mixture was heated up to 80oC. After 5 hours the mixture was cooled to room temperature, filtered, and the filtrate was concentrated under reduced pressure. The residue was diluted with water and concentrated chloroform. The extract was washed with saturated saline solution, dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by chromatographie on silica gel (ethyl acetate), and received 218 mg of target compound (Compound 1-100) (yield 22%).

1H-NMR (CDCl3-TMS) million D.: of 1.27 (d, J= 4,2 Hz, 6H), a 2.36 (s, 3H), of 2.86 (m, 1H), 3,21 (s, 3H), 3,88 (s, 2H), of 6.96 (s, 2H), 7,21 (s, 1H).

Example 101

Synthesis of 2-aminomethyl-5-(3,5-dichlorobenzyl)-4-isopropyl-1-methyl-1H - the l-5-iodo-4-isopropyl-1-methylimidazole (4C), and then for 30 minutes at -70oC was added 5,78 ml (9,83 mmol) n-utility (1.70 M hexane solution). Then, after 5 minutes, for 30 minutes at -70oC was added a solution of 1.56 g (8,91 mmol) of 3,5-dichlorobenzaldehyde dissolved in 10 ml of anhydrous tetrahydrofuran. After 1 hour the mixture was left to cool to room temperature, and then to this mixture was added an aqueous solution of ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline solution, dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (ethyl acetate/methylene chloride = 10/1), and received a 1.25 g of [2-benzoyloxymethyl-5-isopropyl-3-methyl-3H-imidazol-4-yl]-(3,5-dichlorophenyl)-methanol (56) (output 33,3%).

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J= 8,2 Hz, 6H), to 2.94 (m, 1H), 3,38 (s, 3H), of 4.49 (s, 2H), 4,55 (s, 2H), of 5.99 (s, 1H), 7,21~7,39 (m, 8H).

In 20 ml of methylene chloride was dissolved 1.25 g (2,98 mmol) [2-benzoyloxymethyl-5-isopropyl-3-methyl-3H-imidazol-4-yl]- (3,5-dichlorophenyl)methanol (56), and then added to 1.45 g (11.9 mmol) of 4-(dimethylamino)-pyridine at room temperature. After 5 minutes at room temperature was added 0,49 ml (3.54 mmol) finish the second pressure and was purified by chromatography on silica gel (ethyl acetate:hexane = 1:1), the result that was obtained 1.07 g of 2-benzoyloxymethyl-5-(1-(3,5-dichlorophenyl)-1 - phenoxythiocarbonyl)methyl-4-isopropyl-1-methyl-1H-imidazole (57) (output 64,6%).

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J= 6.0 Hz, 6H), of 2.92 (m, 1H), 3.46 in (s, 3H), 4,51 (s, 2H), br4.61 (s, 2H), 6,01 (s, 1H), 6,85~7,42 (m, 13H).

In 20 ml of anhydrous toluene was dissolved 1.07 g (1,93 mmol) 2-benzoyloxymethyl-5-[1-(3,5-dichlorophenyl)-phenoxythiocarbonyl] methyl-4-isopropyl-1-methyl-1H-imidazole (57), and then at room temperature was added 158 mg (0.96 mmol) , azobisisobutyronitrile and 1.14 ml (4,24 mmol) of anti-hydride, and the resulting mixture was heated to 85oC. After 5 hours the reaction mixture was concentrated under reduced pressure and was purified by chromatography on silica gel (ethyl acetate-hexane = 1:1), resulting in a received 470 mg of 2-benzoyloxymethyl-5-(3,5-dichlorobenzyl)-4 - isopropyl-1-methyl-1H-imidazole (58) (yield of 60.5%).

1H-NMR (CDCl3-TMS) million D.: of 1.28 (d, J= 6.8 Hz, 6H), 2,90 (m, 1H), and 3.31 (s, 3H), 3,88 (s, 2H), to 4.52 (s, 2H), 4,63 (s, 2H), 6,94 (s, 2H), 7,22 (s, 1H), 7,30 (s, 5H).

In 3 ml of ethanol was dissolved 470 mg (1,17 mmol) 2-benzoyloxymethyl - 5-(3,5-dichlorobenzyl)-4-isopropyl-1-methyl-1H-imidazole (58), and then added 10 ml of concentrated hydrochloric acid (36% aqueous solution), and the resulting mixture on the m pressure, the neutralized aqueous solution of sodium hydroxide and was extracted with ethyl acetate. The extract was washed with saturated saline solution, dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated. To the crude crystals was added 5 ml of diethyl ether and filtered, resulting in a received 350 mg of [5-(3,5-dichlorobenzyl)-4-isopropyl-1 - methyl-1H-imidazol-2-yl] methanol (59A) (output 95,9%).

1H-NMR (CDCl3-TMS) million D.; 1,22 (d, J= 7,0 Hz, 6H), of 2.92 (m, 1H), 3.45 points (s, 3H), was 4.02 (s, 2H), to 4.62 (s, 2H), 7,06 (s, 2H), 7,29 (s, 1H).

In 5 ml of thionyl chloride was dissolved 160 mg (0.51 mmol) [5-(3,5 - dichlorobenzyl)-4-isopropyl-1-methyl-1H-imidazol-2-yl] -methanol (59A), and the mixture was stirred at room temperature. After 2 hours the reaction mixture was concentrated under reduced pressure, and the obtained residue was added 5 ml of anhydrous dimethylformamide and 80 mg (1,23 mmol) of sodium azide. The mixture is stirred at room temperature for 3 hours, was dissolved with water and was extracted with ethyl acetate. The extract was washed with saturated saline solution, dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated and received 150 mg of 2-azidomethyl-5-(3,5-dichlorobenzyl)-4-isopropyl-1 - methyl-1H-imidazole (60) (yield 87%).

1Nanola was dissolved 150 mg (0.44 mmol) of 2-azidomethyl-5-(3,5-dichlorobenzyl)-4-isopropyl-1-methyl-1H-imidazole (60) and at -20oC was added 50 mg of 10% palladium on coal. The resulting mixture was stirred in a stream of hydrogen at room temperature. After 4 hours the reaction mixture was filtered through celite, and the filtrate was concentrated, resulting in a received 94 mg of the Compound 1-101 (yield 68%).

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J = 6.6 Hz, 6H), 3,37 (s, 3H), with 3.89 (s, 2H), 3,95 (width, 2H), as 4.02 (s, 2H), 6,95 (s, 2H), 7,21 (s, 1H).

Example 102

Synthesis of [5-(3-Chlorobenzyl)-4-isopropyl-1-methyl-1H-imidazol-2-yl] methanol (Compound 1-102)

[2-(Benzoyloxymethyl)-5-isopropyl-3-methyl - 3H-imidazol-4-yl] -(3-chlorophenyl)methanol (56') was obtained from (4C) and 3-chlorobenzaldehyde the method described in example 101 to obtain the compound (56).

1H-NMR (CDCl3-TMS) million D.: of 1.23 (d, J = 8,2 Hz, 6H), 2,96 (m, 1H), 3,34 (s, 3H), 4,47 (s, 2H), 4.53-in (s, 2H), 6,02 (s, 1H), 7,12~the 7.43 (m, 9H).

2-Benzoyloxymethyl-5-(3-Chlorobenzyl)-4-isopropyl-1-methyl-1H-imidazole (58') was obtained from compound (56') in the manner described in example 101 synthesis (58).

1H-NMR (CDCl3-TMS) million D.: of 1.28 (d, J = 6.8 Hz, 6H), 2.91 in (m, 1H), 3,30 (s, 3H), 3,90 (s, 2H), to 4.52 (s, 2H), 4,63 (s, 2H), 6.90 to (m, 1H), 7,20 (m, 2H), 7,30 (m, 5H).

Connection 1-102 received from (58') in the same manner that was described in example 101 to obtain the compound (59A). The oily product~7,35 (m, 2H).

Example 103

Synthesis of 2-carbamoyloxymethyl-5-(3,5-dichlorobenzyl)- 4-isopropyl-1-methyl-1H-imidazole (Compound 1-103)

In 5 ml of anhydrous tetrahydrofuran was dissolved 167 mg (0,53 mmol) [5- (3,5-dichlorobenzyl)-4-isopropyl-1-methyl-1H - imidazol-2-yl] methanol (59A), and at room temperature was added 50 μl (0.59 mmol) characaterization, after which the mixture is stirred. After 1 hour the mixture was diluted with water and extracted with ethyl acetate, and the extract was washed with saturated saline solution, dried with anhydrous sodium sulfate and filtered. The filtrate was concentrated and received 210 mg of 2-N-chloroacetoacetate-5-(3,5 - dichlorobenzyl)-4-isopropyl-1-methyl-1H-imidazole (62) (yield 99%).

1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J= 6.6 Hz, 6H), 2,90 (m, 1H), 3,39 (s, 3H), 3,92 (s, 2H), of 4.44 (s, 2H), 5,26 (s, 2H), 6,94 (s, 2H), 7,25 (s, 1H), 8,55 (width, 1H).

In 20 ml of methanol was dissolved 210 mg (of 0.53 mmol) of 2-N - chloroacetoacetate-5-(3,5-dichlorobenzyl)-4-isopropyl-1 - methyl-1H-imidazole (62), and then at room temperature was added 2 g (30,60 mmol) of zinc, and the mixture was stirred. After 4 hours the reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (MS) million D.: 1,27 (d, J=4,6 Hz, 6H), 2,90 (m, 1H), on 3.36 (s, 3H), 3,91 (s, 2H), 4,85 (width, 2H), 5,17 (s, 2H), 6,95 (s, 2H), 7.23 percent (s, 1H).

Elemental analysis (C16H19N3O2Cl2)

Calculated (%): C 53,94 H 5,38 N 11,80 Cl 19,90

Found (%): C 53,94 H 5,43 N 11,59 Cl 19,66.

Example 104

Synthesis of 5-(3,5-dimethylbenzenesulfonyl)-4-isopropyl-1,2-dimethyl - 1H-imidazole (Compound 1-104)

In methylene chloride (10 ml) was dissolved 150 mg (0.55 mmol) of 5-(3,5-dimethylphenyl)-4-isopropyl-1,2-dimethyl-1H-imidazole, and then under ice cooling was added 177 mg (0.82 mmol) of 80% meta-chloroperbenzoic acid, and the mixture was stirred for 10 minutes. To the reaction mixture was added aqueous sodium thiosulfate solution and then an aqueous solution of sodium bicarbonate and was extracted with methylene chloride. The extract was washed with saturated saline solution, dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate) and recrystallized from n-hexane, resulting in received 100 mg of Compound 1-104 (yield 63%). So pl. 100-101oC.

1H-NMR (CDCl3-TMS) million D.: 1,36 (d, J= 7,0 Hz, 3H), of 1.37 (d, J= 7,0 Hz, 3H), of 2.33 (s, 3H), of 2.35 (s, 3H), 3,26 (s, 3H), 3,32 (Sept., 1H), 7,06 (m, 3H).

Elementry is S="ptx2">

Example 105

Synthesis of 5-(3,5-dimethylbenzenesulfonyl)-4-isopropyl-1,2-dimethyl - 1H-imidazole (Compound 1-105)

In methylene chloride (6 ml) was dissolved 60 mg (0.20 mmol) of 5-(3,5-dimethylphenyl)-4-isopropyl-1,2-dimethyl-1H-imidazole, and then added 223 mg (1.00 mmol) of 80% metallocarboranes acid, and the mixture was stirred for 1 hour at room temperature. To the reaction mixture was added aqueous sodium thiosulfate solution and then an aqueous solution of sodium bicarbonate, and the mixture was extracted with methylene chloride. The extract was washed with saturated saline solution and dried with anhydrous sodium sulfate, and the filtrate was concentrated under reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate) and recrystallized from n-hexane, resulting in received 24 mg of Compound 1-105 (yield 39%). So pl. 126-128oC.

1H-NMR (CDCl3-TMS) million D.: of 1.29 (d, J=6.8 Hz, 6H), a 2.36 (s, 3H) and 3.59 (s, 3H), 3,82 (Sept., 1H), 7,19 (s, 1H), 7,46 (s, 2H).

Example 106

Synthesis of [5-(3,5-dimethylbenzenesulfonyl)-4-isopropyl-1-methyl-1H - imidazol-2-yl]methanol (Compound 1-106)

Compound 1-106 received from Compounds 1-9 in the manner described in example 104. So pl. 125oC,

1H-NMR (CDCl3-TMS) million D.: of 1.29 (d, J = 6,8 Hz, -(3,5-dimethylbenzenesulfonyl)-4-isopropyl-1-methyl-1H - imidazol-2-yl]methanol (Compound 1-107)

Compound 1-107 received from Compounds 1-9 in the manner described in example 105. So pl. 180-182oC

1H-NMR (CDCl3-TMS) million D.: of 1.16 (d, J=6.8 Hz, 6H), of 2.38 (s, 3H), of 3.73 (s, 3H), 3,74 (Sept., 1H), 4,40 (width, 1H), of 4.66 (s, 2H), 7,21 (s, 1H), 7,47 (s, 2H).

Example 108

Synthesis of [5-(3,5-dichlorobenzenesulfonyl)-4-isopropyl-1-methyl-1H - imidazol-2-yl]methanol (Compound 1-108)

Compound 1-108 received from Compounds 1-8 in the same manner that was described in example 104. So pl. 128-130oC.

1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J= 5.0 Hz, 3H), of 1.28 (d, J = 5.0 Hz, 3H), 3,26 (Sept., 1H), 3.46 in (s, 3H) and 4.65 (s, 2H), 7,37 (d, J=1.4 Hz, 2H), 7,46 (t, J=1.4 Hz, 1H).

Elemental analysis (C14H16Cl2N2O2S)

Calculated (%): C 48,42 H with 4.64 N 8,07 S 9,23 Cl 20,42

Found (%): C 48,27 H 4,73 N 7,99 S 9,23 Cl 20,60.

Example 109

Synthesis of [5-(3,5-dichlorobenzenesulfonyl)-4-isopropyl-1-methyl-1H - imidazol-2-yl]methanol (Compound 1-109)

Compound 1-109 received from Compounds 1-8 in the manner described in example 105. So pl. 202-204oC.

1H-NMR (CDCl3-TMS) million D.: 1,22 (d, J=4.4 Hz, 6H), 3,71 (Sept., 1H), 4,69 (s, 2H), 7,56 (t, J= 1.2 Hz, 1H), 7,72 (d, J= 1.2 Hz, 2H).

Example 110

Synthesis of 2-aminomethyl-5-(3,5-dichlorobenzenesulfonyl)-4-isopropyl - 1-methyl-1H-imidazole (Compound 1-110)

Soy is/SUP>H-NMR (CDCl3-TMS) million D.; 1,36 (d, J =4,6 Hz, 3H), of 1.37 (d, J= 4,6 Hz, 3H), 3,29 (Sept., 1H), 3,38 (s, 3H), 3,88 (s, 2H), 7,38 (d, J= 1.2 Hz, 2H), 7,45 (t, J=1.2 Hz, 1H).

Example 111

Synthesis of 2-aminomethyl-5-(3,5-dichlorobenzenesulfonyl)-4-isopropyl - 1-methyl-1H-imidazole (Compound 1-111)

Compound 1-111 was obtained from Compound 1-66 method described in example 105. The oily product.

1H-NMR (CDCl3-TMS) million D.: 1,15 (d, J= 4.4 Hz, 3H), 3,69 (Sept., 1H), 3,81 (s, 3H), 4,70 (width, 2H), 7,56 (t, J=1.2 Hz, 1H), 7,71 (d, J= 1.2 Hz, 2H).

Example 112

Synthesis of 5-(3,5-dichlorobenzenesulfonyl)-4-isopropyl-1-methyl-2 - triptoreline-1H-imidazole (Compound 1-112)

Compound 1-112 was obtained from the compound (40C) in the manner described in example 104. The oily product.

1H-NMR (CDCl3-TMS) million D.: of 1.35 (d, J=6.8 Hz, 3H), of 1.36 (d, J= 6.8 Hz, 3H), 3,29 (Sept., 1H), 3,38 (s, 3H), of 4.49 (DD, 5,2 Hz, 1.6 Hz, 2H), 7,37 (d, J= 1.8 Hz, 2H), 7,47 1.8 Hz, 1H).

Example 113

Synthesis of [5-(3,5-dichlorobenzenesulfonyl)-4-isopropyl-1H-imidazol - 2-yl]methanol (Compound 1-113)

Compound 1-113 was obtained from the compound (12) (R1= H) by the method described in example 104. So pl. 217-218oC.

1H-NMR (DMSO-d6-TMS) million D.: of 1.27 (d, J= 7,0 Hz, 3H), 1,32 (d, J= 7,0 Hz, 3H), 3,37 (Sept., 1H), 4,34 (d, J=5.8 Hz, 2H), 5,46 (t, J= 5.8 Hz, 1H), 7,53 (d, J= 1.6 Hz, (%): C 46,86 H 4,23 to 8.41 N S 9,62 Cl 21,28

Found (%): C 46,73 H 4,34 N 8,15 S 9,39 Cl 21,13.

Example 114

Synthesis of [5-(3,5-dichlorobenzenesulfonyl)-4-isopropyl-1H-imidazol - 2-yl]methanol (Compound 1-114)

Compound 1-114 was obtained from the compound (12) (R1= H) by the method described in example 105. So pl. 217oC.

1H-NMR (DMSO-d6-TMS) million D.; to 1.23 (d, J=6.6 Hz, 6H), of 3.75 (m, 1H), 4,39 (d, J= 5.6 Hz, 2H), 5,50 (t, J= 5.6 Hz, 1H), 7,80 (d, J= 1.6 Hz, 2H), 7,98 (t, J= 1.6 Hz, 1H), 12,81 (width, 1H).

Elemental analysis (C13H14Cl2N2O3S)

Calculated (%): C 44,71 H 4,04 N 8,02 S 9,18 Cl 20,30

Found (%): C 44,94 H 4,11 Of 7.90 N S 8,91 Cl 20,12.

Example 115

Synthesis of 2-carbamoyloxymethyl-5-(3,5-dichlorobenzenesulfonyl)-4 - isopropyl-1-methyl-1H-imidazole (Compound 1-115)

Compound 1-115 was obtained from Compound 1-41 method described in example 104.

So pl. 148-149oC.

1H-NMR (DMSO-d6-TMS) million D.: of 1.37 (d, J=7.2 Hz, 3H), of 1.39 (d, J= 7.2 Hz, 3H), and 3.31 (Sept., 1H), 3,44 (s, 3H), 4,70 (width, 2H), 5,13 (s, 2H), 7,38 (d, J= 1.8 Hz, 2H), 7,47 (t, J= 1.8 Hz, 1H).

Elemental analysis (C15H17Cl2N3O3S)

Calculated (%): C 46,16 H 4,39 N 10,77 S By 8.22 Cl 18,17

Found (%): C 45,94 H 4,45 N 10,61 S 8,02 Cl 18,36.

Example 116

Synthesis of 1-(p-t-butylbenzyl)-5-(3,5-dichlorophenylthio)-2 - hydroxymethyl-4-isopropyl-1H-is 152 mg of potassium iodide, cooling in this ice, after which the mixture was left to warm to room temperature and stirred for 20 minutes. Then added 200 mg of 5-(3,5-dichlorophenylthio)- 4-isopropyl-2-(p-methoxybenzyloxy)-1H-imidazole (101b), and then was added 126 mg of potassium carbonate, and the resulting mixture was heated to 50oC. Then the mixture was left for reaction for 6 hours. After completion of the reaction the mixture was diluted with water, was extracted with diethyl ether, the extract was dried with anhydrous sodium sulfate, and the solvent is kept at reduced pressure. To the thus obtained oily product was added 5 ml of ethanol and 10 ml of 36% hydrochloric acid, and the mixture is stirred 2 hours at 90oC. After completion of the reaction the solvent is kept at reduced pressure, the obtained crystals were washed with diethyl ether and filtered, resulting in a received 220 mg of Compound 1-116 (yield 96%).

So pl. 174-177oC.

1H-NMR (CD3OD-TMS) million D.: 1,22 (s, 9H), of 1.35 (d, J= 7,0 Hz, 6H), 3,30 (Sept. , 1H), 5,02 (s, 2H), 5,44 (s, 2H), 6,72 (d, J= 1.8 Hz, 2H), 7,05~of 7.25 (m, 5H).

Example 117

Synthesis of 1-(p-N-acetylaminobenzoic)-5-(3,5-dichlorophenylthio)-2 - hydroxymethyl-4-isopropyl-1H-imidazole (Compound 1-117)

In dimethylformamide was added prda room temperature and stirred for 20 minutes. Then to the mixture was added 200 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxy)- 1H-imidazole (101b), and then was added 76 mg of potassium carbonate. At the beginning of the reaction, the reaction mixture had a green color, but this color soon disappeared. Then the mixture was heated to 50oC and left for 3 hours to undergo reaction. After completion of the reaction the mixture was diluted with water, was extracted with diethyl ether, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. To the thus obtained oily substance was added 5 ml of ethanol and 10 ml of 36% hydrochloric acid, and the mixture is stirred for 2 hours at 90oC. After completion of the reaction the solvent drove away under reduced pressure. To the residue was added an aqueous solution of sodium bicarbonate, the mixture was extracted with ethyl acetate, the extract was dried with sodium sulfate, the solvent is kept at reduced pressure. The crystals were washed with diethyl ether, filtered and received 150 mg of 5-(3,5 - dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1-(p-nitrobenzyl)-1H - imidazole (103A) (yield 73%). So pl. 192-194oC.

1H-NMR (CD3OD-TMS) million D.: a 1.25 (d, J= 7,0 Hz, 6H), 3,12 (Sept., 1H), 4,79 (s, 2H), vs. 5.47 (s, 2H), return of 6.58 (d, J=2.0 Hz, 2H), 6,99 (d, 1H), 7,32 (d is propyl-1-(p-nitrobenzyl)-1H-imidazole (103A) and added charcoal coated with a sulfur platinum. After replacing the reaction medium in an atmosphere of hydrogen and the mixture was subjected to catalytic hydrogenation at atmospheric pressure and room temperature. After 1 hour the mixture was filtered through celite, the filtrate is kept under reduced pressure and to the residue was added diethyl ether. Precipitated crystals were filtered and received 579 mg of 1-(p-aminobenzyl)-5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl - 1H-imidazole (a) (Yield 78%). So pl. 130oC (Razlog.).

1H-NMR (CDCl3-TMS) million D.: 1,19 (d, J= 7,0 Hz, 6H), is 3.08 (Sept., 2H), 4,28 (Shir. , 2H), and 4.75 (s, 2H), 5,12 (s, 2H), to 6.43 (d, J= 8,2 Hz, 2H), 6,60 (d, 2H), 6,80 (d, J= 8,2 Hz, 2H), 7,00 (d, 1H).

The methylene chloride was dissolved 200 mg of 1-(p-aminobenzyl)-5-(3,5 - dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1H-imidazole (a), and then under ice cooling was added 116 mg dimethylaminopyridine and 212 μl of acetic anhydride, and the mixture was left to warm to room temperature and stirred for 1 hour. After completion of the reaction the mixture was diluted with water, extracted with methylene chloride, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. The residue was purified by chromatography on silica gel (methylene chloride:ethyl acetate = 2:1) and obtained 2 - acetoxymethyl-1-the under ice cooling was added a 1 M solution of sodium methoxide. Then the mixture was left to warm to room temperature and stirred for 1 hour. After completion of the reaction the solvent is kept under reduced pressure and was received by 41.2 mg of Compound 1-117 (yield 10%).

1H-NMR (CDCl3-TMS) million D.:, 1,22 (d, J=7,0 Hz, 6H), of 2.16 (s, 3H), 3,10 (Sept. , 1H), 4.72 in (s, 2H), 5,19 (s, 2H), 6,62 (d, J= 1.8 Hz, 2H), 6.87 in~7,38 (m, 5H).

Example 118

Synthesis of 1-(m-aminobenzyl)-5-(3,5-dichlorophenylthio)-2 - hydroxymethyl-4-isopropyl-1H-imidazole (Compound 1-118)

The dimethylformamide was added 94 mg m-nitrobenzylamine and 114 mg of potassium iodide under ice cooling, and then the mixture was left to warm to room temperature and stirred for 20 minutes. After this was added 200 mg of 5-(3,5 - dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxy)-1H - imidazole (101b), and then was added 76 mg of potassium carbonate. The resulting mixture was heated to 50oC and left for 6 hours to undergo reaction. After completion of the reaction the mixture was diluted with water, was extracted with diethyl ether, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. To the thus obtained oily substance was added 5 ml of ethanol and 10 ml of 36% hydrochloric acid, and the mixture is stirred 2 hours at R sodium bicarbonate and ethyl acetate. Insoluble materials in both layers was filtered and obtained 72 mg of 5-(3,5-dichlorophenylthio)-2 - hydroxymethyl-4-isopropyl-1-(m-nitrobenzyl)-1H-imidazole hydrochloride. An ethyl acetate layer of the filtrate was dried with sodium sulfate, and the solvent is kept at reduced pressure. The crystals were washed with diethyl ether, filtered and received 80 mg of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1-(m-nitrobenzyl)- 1H-imidazole (103b) (71% yield). 103b, so pl. 197-198oC.

1H-NMR (CD3OD-TMS) million D.; 1,25 (d, J=7,0 Hz, 6H), 3,10 (Sept., 1H), to 4.81 (s, 2H), vs. 5.47 (s, 2H), 6,53 (d, J=1.8 Hz, 2H), 6,99 (d, 1H), 7,32 (d, 1H), to 7.59 (d, 1H), 7,89 (d, 1H), 8,00 (s, 1H).

Hydrochloride compound 103b

1H-NMR (CD3OD-TMS) million D.: of 1.37 (d, J = 7,0 Hz, 6N), 3,36 (Sept., 1H), is 5.06 (s, 2H), 5,64 (s, 2H), of 6.68 (d, J= 1.6 Hz, 2H), 7,12 (d, J= 1.6 Hz, 1H), 7,45 (d, J= 8,2 Hz, 1H), 7,63 (d, 1H), to 7.99 (d, 1H), 8,07 (s, 1H).

Elemental analysis (C20H19Cl2N3O3SHCl1,1H2O)

Calculated (%): C 47,23 H 4,40 compared to 8.26 N Cl To 20.91 S 6,30

Found (%): C 47,06 H 4,42 of 8.37 N Cl 20,98 S OF 6.49

The ethyl acetate was dissolved 64 mg of 5-(3,5-dichlorophenylthio)-2 - hydroxymethyl-4-isopropyl-1-(m-nitrobenzyl)-1H-imidazole (103b), and then added sulfur platinum on coal. After replacing the reaction medium atmosphere of hydrogen and the mixture was subjected to catalytic heartrate drove under reduced pressure and added to diethyl ether. Precipitated crystals were filtered and received 25 mg of Compound 1-118 (yield 42%). So pl. 145-148oC.

1H-NMR (CDCl3-TMS) million D.: 1,22 (d, J=7,0 Hz, 6H), 3,11 (Sept., 1H), 4,71 (s, 2H), 5,13 (s, 2H), 6,21 (s, 2H), 6,32 ~6,50 (m, 2H), of 6.68 (d, J= 1.8 Hz, 2H), of 6.96 (m, 1H), 7,01 (d, J= 1.8 Hz, 1H).

Example 119

Synthesis of 1-(o-aminobenzyl)-5-(3,5-dichlorophenylthio)-2-hydroxymethyl - 4-isopropyl-1H-imidazole (Compound 1-119)

In dimethylformamide was added 237 mg on-nitrobenzylamine and 228 mg of potassium iodide under ice cooling, after which the mixture was left to warm to room temperature and stirred for 20 minutes. Then added 400 mg of 5-(3,5-dichlorophenylthio)-4 - isopropyl-2-(p-methoxybenzyloxy)-1H-imidazole (101b), and then added 152 mg of potassium carbonate. The resulting mixture was heated to 50oC and left for 6 hours to undergo reaction. After completion of the reaction the mixture was diluted with water, was exteremely diethyl ether, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. To the thus obtained oily substance was added 10 ml of ethanol and 20 ml of 36% hydrochloric acid, and the mixture is stirred 2 hours at 90oC. After completion of the reaction the solvent drove away under reduced pressure, adding water drove away under reduced pressure. The crystals were washed with diethyl ether, filtered and received 195 mg of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl - 1-(o-nitrobenzyl)-1H-imidazole (s) (Yield 47%). So pl. 160 - 166oC.

1H-NMR (CDCl3-TMS) million D.: 1,31 (d, J= 6.6 Hz, 6H), 3,19 (Sept., 1H), and 4.75 (s, 2H), 5,65(s, 2H), 6,51 (d, 1H), 6,70 (d, J= 1.6 Hz, 2H), 7,00 (d, J= 1.6 Hz, 1H), 7,37 (m, 2H), 8,03 (d, 1H).

Elemental analysis (C20H19Cl2N3O3S)

Calculated (%); C 53,10 H 4,23 N 9,29 Cl 15,67 S 7,09

Found (%): C 53,03 H Of 4.44 N 9,38 Cl 15,38 S 6,99.

The ethyl acetate was dissolved 170 mg of 5-(3,5-dichlorophenylthio)-2 - hydroxymethyl-4-isopropyl-1-(o-nitrobenzyl)-1H-imidazole (s) was added sulfur platinum on coal. After replacing the reaction medium with an atmosphere of hydrogen was carried out by catalytic hydrogenation at atmospheric pressure and at room temperature. After 1 hour the mixture was filtered through celite, and the filtrate is kept under reduced pressure. To the residue was added diethyl ether, the precipitated crystals were collected by filtration and received 77 mg of Compound 1-119 (yield 49%).

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J= 6.6 Hz, 6H), of 3.12 (Sept, 1H), 4,63 (S, 2H), 5,20 (s, 2H), 6,50~7,25 (m, 4H), of 6.66 (d, 2H), of 6.96 (d, 1H).

Example 120

Synthesis of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1- (1 is Talina and 152 mg of potassium iodide under ice cooling, then the mixture was left to warm to room temperature and stirred for 20 minutes. Then added 200 mg of 5-(3,5-dichlorophenylthio)-4 - isopropyl-2-(p-methoxybenzyloxy)-1H-imidazole (101b) with the subsequent addition of 126 mg of potassium carbonate. The resulting mixture was heated to 50oC and left for 6 hours to undergo reaction. After completion of the reaction the mixture was diluted with water and was extracted with diethyl ether. The extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. To the thus obtained oily substance was added 5 ml of ethanol and 10 ml of 36% hydrochloric acid, and the mixture is stirred for 2 hours at 90oC. After completion of the reaction the solvent drove away under reduced pressure. The crystals were washed with diethyl ether, filtered and received 220 mg of Compound 1-120 (yield 97%). So pl. 135-140oC.

1H-NMR (CD3OD-TMS) million D.: of 1.42 (d, J=7.2 Hz, 6H), 3.43 points (Sept., 1H), to 4.98 (s, 2H), of 5.99 (s, 2H), to 6.57 (d, J=1.8 Hz, 2H), 6,78 (d, 1H), 7,03 (d, J= 1.8 Hz, 1H), 7,25 (m, 1H), 7,45~for 7.78 (m, 3H), a 7.85 (d, 1H), 8,13 (d, 1H).

Example 121

Synthesis of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1- (2-phenylethyl)-1H-imidazole (Compound 1-121)

To dry tetrahydrofuran was added 44 mg powder g mg 5-(3,5 - dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxy)-1H - imidazole (101b). After 20 minutes, to this mixture was added 129 μl of 1-bromo-2-phenylethane. After 3 hours stirring at room temperature the mixture was diluted with water, was extracted with diethyl ether, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. To the thus obtained oily substance was added 10 ml of ethanol and 20 ml of 36% hydrochloric acid, and the mixture is stirred for 2 hours at 90oC. After completion of the reaction the solvent drove away under reduced pressure, to the residue was added aqueous sodium bicarbonate solution, extracted with ethyl acetate, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. The residue was purified by chromatography on silica gel (hexane: ethyl acetate = 1: 1) and received 100 mg of Compound 1-121 (yield 52%).

1H-NMR (CDCl3-TMS) mn d: 1,19 (d, J=7,0 Hz, 6H), is 2.88 (m, 2H), 3,05 (Sept. , 1H), 4,19 (m, 2H), 4,89 (s, 2H), at 6.84 (d, J= 1.8 Hz, 2H), 6,98~7,39 (m, 5H), 7,12 (d, J= 1.8 Hz, 1H).

Elemental analysis (C21H22Cl2N2OS)

Calculated (%): C 59,86 H 5,26 N 6,65 Cl equal to 16.83 S TO 7.61

Found (%): C 59,93 H 5,52 N 6,54 Cl 16,00 S 7,33.

Example 122

Synthesis of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1- (3-phenylpropyl)-1H-imidazole (Compound 1-122)

To be the harfenist)-4-isopropyl-2-(p-methoxybenzyloxy)-1H - imidazole (101b). After 20 minutes was added 136 μl of 1-bromo-3 - phenylpropane. After 3 hours stirring at room temperature the mixture was diluted with water and was extracted with diethyl ether. The extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. To the thus obtained oily substance was added 10 ml of ethanol and 20 ml of 36% hydrochloric acid, after which the mixture is stirred for 2 hours at 90oC. After completion of the reaction the solvent drove away under reduced pressure, then added an aqueous solution of sodium bicarbonate and was extracted with ethyl acetate. The extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. The residue was purified by chromatography on silica gel (hexane:ethyl acetate = 1:1) and received 80 mg of the Compound 1-122 (yield 40%).

1H-NMR (CDCl3-TMS) million D.: 1,19 (d, J= 6.6 Hz, 6H), 1.93 and (m, 2H), 2,61 (m, 2H), 3,05 (Sept., 1H), 3,92 (m, 2H), and 4.68 (s, 2H), 6.75 in (d, J= 1.8 Hz, 2H), 7,01~of 7.36 (m, 6H).

Elemental analysis (C22H24Cl2N2OS)

Calculated (%): C 60,69 H 5,56 N To 6.43 Cl 16.28 Per S OF 7.36

Found (%): C 60,57 H 5,64 N 6,41 Cl 16,01 S 7,43.

Example 123

Synthesis of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1- (4-phenylbutyl)-1H-imidazole (Compound 1-123)

To dimethylformamidine to room temperature and stirred for 20 minutes. Then added 200 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl - 2-(p-methoxybenzyloxy)-1H-imidazole (101b) with the subsequent addition of 126 mg of potassium carbonate. After that, the mixture was heated to 50oC and left for 6 hours to undergo reaction. After completion of the reaction the mixture was diluted with water, was extracted with diethyl ether, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. To the thus obtained oily substance was added 10 ml of ethanol and 20 ml of 36% hydrochloric acid, after which the mixture is stirred for 2 hours at 90oC. After completion of the reaction the solvent drove away under reduced pressure, then added an aqueous solution of sodium bicarbonate and was extracted with ethyl acetate. The extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. The residue was purified by chromatography on silica gel (hexane:ethyl acetate = 1:1) and received 86 mg of the Compound 1-23 (yield 42%).

1H-NMR (CDCl3-TMS) million D.: 1,15 (d, J=6.6 Hz, 6H), to 1.61 (m, 4H), of 2.54 (m, 2H), 3,03 (Sept., 1H), 3,98 (m, 2H), 4,71 (s, 3H), 6,78 (s, 2H), 7,01~ 7,39 (m, 6H).

Example 124

Synthesis of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1- (5-fenilpentil)-1H-imidazole (compound 1-124)

To dimethylformamidine to room temperature and stirred for 20 minutes. Then added 200 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl - 2-(p-methoxybenzyloxy)-1H-imidazole (101b) with the subsequent addition of 126 mg of potassium carbonate. After that, the mixture was heated to 50oC and left for 6 hours to undergo reaction. After completion of the reaction the mixture was diluted with water, was extracted with diethyl ether, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. To the thus obtained oily substance was added 10 ml of ethanol and 20 ml of 36% hydrochloric acid, after which the mixture is stirred for 2 hours at 90oC. After completion of the reaction the solvent drove away under reduced pressure, and then added an aqueous solution of sodium bicarbonate and was extracted with ethyl acetate. The extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. The residue was purified by chromatography on silica gel (hexane:ethyl acetate = 1:1) and received 120 mg of Compound 1-124 (yield 57%).

1H-NMR (CDCl3-TMS) million D.: of 1.16 (d, J= 7,0 Hz, 6H), of 1.30 (m, 2H), 1,58 (m, 4H), of 2.53 (m, 2H), 3,05 (Sept., 1H), 3.96 points (m, 2H), 4,74 (s, 2H), 6,80 (d, J= 1.8 Hz, 2H), 7,07~7,34 (m, 6H).

Example 125

Synthesis of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl - 1-(6-phenylhexa)-1H-imidazole (Compound 1-125)

about the mixture was left to warm to room temperature and stirred for 20 minutes. Then added 200 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl - 2-(p-methoxybenzyloxy)-1H-imidazole (101b) with the subsequent addition of 126 mg of potassium carbonate. After that, the mixture was heated to 50oC and left for 6 hours to undergo reaction. After completion of the reaction the mixture was diluted with water, was extracted with diethyl ether, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. To the thus obtained oily substance was added 10 ml of ethanol and 20 ml of 36% hydrochloric acid, and the mixture is then stirred for 2 hours at 90oC. After completion of the reaction the solvent drove away under reduced pressure, and then added an aqueous solution of sodium bicarbonate and was extracted with ethyl acetate. The extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. The residue was purified by chromatography on silica gel (hexane:ethyl acetate = 1:1), and received 81 mg of the Compound 1-125 (yield 37%).

1H-NMR (CDCl3-TMS) million D.: 1,17 (d, J= 7,0 Hz, 6H), 1.26 in

(m, 4H), of 1.53 (m, 4H), 2,52 (m, 2H), 3,05 (Sept., 1H), 3,92 (m, 2H), to 4.73 (s, 2H), 6,80 (d, J= 1.6 Hz, 2H), 7.03 is~7,34 (m, 6H).

Example 126

Synthesis of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl - 1-(2-thienylmethyl)-1H-imidazole hydrochloride (Som ice, then the mixture was left to warm to room temperature and stirred for 20 minutes. Then added 200 mg of 5-(3,5-dichlorophenylthio)-4 - isopropyl-2-(p-methoxybenzyloxy)-1H-imidazole (101b) with the subsequent addition of 126 mg of potassium carbonate. After that, the mixture was heated to 50oC and left for 6 hours to undergo reaction. After completion of the reaction the mixture was diluted with water, was extracted with diethyl ether, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. To the thus obtained oily substance was added 5 ml of ethanol and 10 ml of 36% hydrochloric acid, and the mixture is then stirred for 2 hours at 90oC. After completion of the reaction, the solvent is kept at reduced pressure. The crystals were washed with diethyl ether and filtered, resulting in a received 170 mg of the Compound 1-126 (yield 83%).

1H-NMR (CD3OD-TMS) million D.: 1,32 (d, J= 7,0 Hz, 6H), 3,32 (Sept., 1H), 5,04 (s, 2H), of 5.68 (s, 2H), to 6.80 (m, 1H), 6,86 (d, 2H), 7,05 (m, 1H), 7,26 (m, 1H), 7,32 (m, 1H).

Example 127

Synthesis of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl - 1-(3-thienylmethyl)-1H-imidazole hydrochloride (Compound 1-127)

In dimethylformamide was added under ice cooling 67 mg of 3-(chloromethyl)thiophene and 152 mg of iodide was added 200 mg of 5-(3,5-dichlorophenylthio)- 4-isopropyl-2-(p-methoxybenzyloxy)-1H-imidazole (101b) with the subsequent addition of 126 mg of potassium carbonate. After that, the mixture was heated to 50oC and left for 6 hours to undergo reaction. After completion of the reaction the mixture was diluted with water, was extracted with diethyl ether, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. To the thus obtained oily substance was added 5 ml of ethanol and 10 ml of 36% hydrochloric acid, and the mixture is then stirred for 2 hours at 90oC. After completion of the reaction the solvent drove away under reduced pressure. The crystals were washed with diethyl ether and filtered, resulting in the received 200 mg of the Compound 1-127 (yield 97%).

1H-NMR (CD3OD-TMS) million D.: of 1.33 (d, J=7,0 Hz, 6H), 3,32 (Sept., 1H), free 5.01 (s, 2H), 5,49 (s, 2H), PC 6.82 (d, J= 1.8 Hz, 2H), 7,01 (m, 1H), 7.23 percent (d, J= 1.8 Hz, 1H), 7,25~7,40 (m, 2H).

Example 128

Synthesis of 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl - 1-(quinoline-3-ylmethyl)-1H-imidazole (Compound 1-128)

In tetrahydrofuran (10 ml) was dissolved 245 mg (2 mmol) 2-benzoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imizol (101a). To this solution, stirring at room temperature, was added methylenechloride solution of quinoline-3-ylmethylboronic, after which was added 200 mg (5 mmol) of sodium hydroxide and 39 mg (0.12 mmol) of the bromide n-tetrobot mesh drove away under reduced pressure. The residue was extracted with methylene chloride, and the extract was washed with water and drained. The solvent is kept off, and the oily residue was purified by chromatography on silica gel (methylene chloride-ethyl acetate). As the first eluate was obtained 26 g (2,6%) 2-benzoyloxymethyl-4-(3,5-dichlorophenylthio)-5 - isopropyl-1-(quinoline-3-ylmethyl)-1H-imidazole (100A). From the subsequent eluate was received 730 mg of 2-benzoyloxymethyl-5-(3,5-dichlorophenylthio)-4 - isopropyl-1-(quinoline-3-ylmethyl)-1H-imidazole (100b) (yield 73%), so pl. 95-98oC. the resulting product was suitable for use in the subsequent reaction stage.

1H-NMR (CDCl3) million D.: (100A) of 1.29 (d, J= 6.8 Hz, 6H), 3,05~3,2 (m, 2H), 4,60 (s, 2H), 4,74 (s, 2H), to 5.35 (s, 2H), 6,5 (d, J=1.6 Hz, 2H), 6,59 (t, J=1.8 Hz, 1H), 7.5 to~to 7.75 (m, 4H), 8,91 (d, J= 9.8 Hz, 1H), 8,7 (d, J= 2.2 Hz).

(100b) of 1.18 (d, J= 7.2 Hz, 6H), 2,9~3,2 (m, 1H), to 4.52 (s, 2H), 4,63 (s, 2H), vs. 5.47 (s, 2H), 6,99 (d, J= 1.6 Hz, 2H), to 7.09 (t, J=2 Hz, 1H), 7,46-7,58 (m, 2H), to 7.67-to 7.68 (m, 2H), 8,11 (d, J=8,2 Hz, 2H), 8,76 (d, J= 2.4 Hz, 1H).

In 10 ml of con. HCl was dissolved 730 mg (1,36 mmol) 2-benzoyloxymethyl - 5-(3,5-dichlorophenylthio)-4-isopropyl-1-(quinoline-3-ylmethyl)-1H-imidazole (100b), after which the mixture was heated under reflux for 1 hour and left. Then to the reaction mixture were added saturated aqueous sodium bicarbonate solution, was extracted with metranil is using chromatography on silica gel (ethyl acetate) and received 500 mg of 2-hydroxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl - 1-(quinoline-3-ylmethyl)-1H-imidazole (109) (yield 83%). So pl. 174-175oC.

1H-NMR (CDCl3) million D.: of 1.26 (d, J= 6.8 Hz, 6H), 3,0~3,2 (m, 1H), 2,6~ 3.8V (Shir. 1H), to 4.87 (s, 2H), 5,44 (s, 2H), of 6.52 (d, J= 1.8 Hz, 2H), 6,61 (t, J= 2 Hz, 1H), 7,47-7,72 (m, 4H), of 8.04 (d, J= 9 Hz, 4H), 8,77 (d, J= 2 Hz, 1H).

Elemental analysis (C23H21N3Cl2OS)

Calculated (%): C 60,26 H 4,62 N 9,17 Cl 15,47 S 6,99

Found (%): C 59,98 H 4,73 remaining 9.08 N Cl 15,11 S 7,10

In 5 ml of tetrahydrofuran was dissolved 223 mg (0.50 mmol) of 2-hydroxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(quinoline-3 - ylmethyl)-1H-imidazole (109), and then stirring at 0oC, one drop was added 72 mg (0,60 mmol) charaterization, and the resulting mixture stirred for 30 minutes at room temperature. After completion of the reaction the mixture was stirred. To the reaction mixture were added saturated aqueous solution of sodium bicarbonate, then extracted with methylene chloride, and the extract was washed with water and drained. The solvent is kept under reduced pressure, and obtained 2-chloroacetoacetate-5-(3,5-dichlorophenylthio)-4 - isopropyl-1-(quinoline-3-ylmethyl)-1H-imidazole (110), which was suitable for use in the next stage. So pl. 167-170oC. the Obtained crystals were dissolved in 20 ml of aqueous methanol was added 40 mg of zinc dust, after which the mixture is stirred for 5 cask this mixture was added a saturated aqueous solution of sodium bicarbonate, and insoluble material was removed by filtration through celite under reduced pressure. The filtrate was concentrated and extracted with methylene chloride, the extract washed with water and dried, and the solvent drove away. The crystalline residue was washed with ethyl acetate and ether, resulting in the received 195 mg of the Compound 1-128 (yield 78%). So pl. 214-216oC.

1H-NMR (CDCl3) million D.: (110): is 1.81 (d, J= 6.8 Hz, 6H), 3,1~of 3.23 (m, 1H), is 4.21 (s, 2H), lower than the 5.37 (s, 2H), of 5.45 (s, 2H), 6,60 (d, J=2 Hz, 2H), 6.73 x (t, J= 1.6 Hz), 7,26~7,73 (m, 4H), 8,15 (d, J= 7.8 Hz, 1H), 8,12 (width, 1H), to 8.62 (d, J=2,4 Hz).

Connection 1-28: of 1.30 (d, J=7 Hz, 6H), 3,1~3,2 (m, 1H), 4,6 (width, 2H), 5,33 (s, 2H), 5,43 (s, 2H), of 6.52 (d, J=2 Hz, 2H), 6,59 (d, J= 1,8 Hz), 7,49~ of 7.69 (m, 4H), of 8.00 (d, J=8,8 Hz, 1H), 8,67 (d, J = 2,6 Hz).

Elemental analysis (C24H22N4Cl2O2S)

Calculated (%): C 57,74 H 4,42 N 11,17 S 6,39 Cl 14,14

Found (%): C 57,30 H 4,50 N 11,08 S 6,59 Cl 13,92.

Example 129

Synthesis of 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl - 1-(2-(2-pyridyl)ethyl)-1H-imidazole (Compound 1-129)

In 10 ml of methylene chloride was dissolved in 2 g of 2-pyridinethiol, the mixture was cooled to -40oC in a bath of dry ice was added 2.5 mg of thienylboronic. Then the mixture was left to heat for 10 minutes, after which the mixture is stirred at 60o is in tertrahydrofuran ring solution, containing 3.6 g of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p - methoxybenzyloxy)imidazole (101b), 650 mg of powdery sodium hydroxide and 262 mg of tetrabutylammonium bromide. Then the temperature was raised to room temperature and was added powdered sodium hydroxide for alkalizing. After 5 hours the mixture was diluted with water, was extracted with diethyl ether, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. The residue was purified by chromatography on silica gel (hexane:ethyl acetate = 2:1), resulting in received of 1.9 g of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p-methoxybenzyloxy)- 1-(2-(2-pyridine)ethyl-1H-imidazole (yield 43%).

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J=7,0 Hz, 6H), is 3.08 (m, 3H), 3,79 (s, 3H), 4,36 (m, 2H), 4,48 (s, 4H), 3.72 points-to 6.95 (m, 5H), 7,07-7,16 (m, 2H), 7,17-7,30 (m, 2H), 7,50 (m, 1H), charged 8.52 (m, 1H).

To 1,43 g of 5-(3,5-dichlorophenylthio)-4-isopropyl-2-(p - methoxybenzyloxy)-1-(2-(2-pyridine)ethyl-1H-imidazole was added 20 ml of ethanol and 40 ml of 36% hydrochloric acid, after which the mixture is stirred for 2 hours at 90oC. At the completion of the reaction the solvent is kept under reduced pressure, and then added an aqueous solution of sodium bicarbonate and was extracted with ethyl acetate. The extract was dried sulfate hydroxide is tracecut: methanol = 10:1), resulting received 571 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl-2 - hydroxymethyl-1-(2-(2-pyridyl)ethyl)-1H-imidazole (a) (51% yield).

1H-NMR (CDCl3-TMS) million D.: of 1.29 (d, J = 6.8 Hz, 6H), 3.15 in (m, 3H), to 4.52 (m, 2H), amounts to 4.76 (s, 2H), 6.87 in (d, 2H), 6,80-7,40 (m, 3H), 7,60 (m, 1H), and 8.50 (m, 1H).

Elemental analysis (C20H21Cl2N3OS)

Calculated (%): C 56,87 H 5,01 N 9,95 Cl 16,79 S TO 7.59

Found (%): C 56,58 H 5,13 N 9,90 Cl 16,65 S 7,53.

In 20 ml of tetrahydrofuran was dissolved 521 mg of 5-(3,5-dichlorophenylthio)- 4-isopropyl-2-hydroxymethyl-1-(2-pyridylethyl)-1H-imidazole (a), and the resulting mixture was cooled to -40oC. Then, while stirring was added 221 μl trichlorotriazine, the mixture was left at room temperature to complete the reaction and stirred for 30 minutes. After adding 500 μl of triethylamine, 5 ml of water and 5 ml of methanol, the mixture is stirred at 70oC for 1 hour. After completion of the reaction the solvent is kept under reduced pressure and to the residue was added aqueous sodium bicarbonate solution and was extracted with ethyl acetate. The extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:methanol = 10:1) and Polen), of 5.11 (s, 2H), 5,31 (width, 2H), at 6.84 (d, 2H), 6,94 (m, 1H), 7,13 (d, 1H), 7,18 (m, 1H), 7,60 (m, 1H), 8,51 (m, 1H).

Example 130

Synthesis of 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl - 1-(3-(2-pyridyl)propyl)-1H-imidazole (Compound 1-130)

In 20 ml of methylene chloride was dissolved 500 mg of 2-pyridinemethanol, after which the mixture was cooled to -40oC in a bath of dry ice and added 564 μl of thienylboronic. Next, the mixture was left for 10 minutes to heat, after which it was stirred at 60oC. After 30 minutes the mixture was cooled and the solvent is kept at reduced pressure. The residue was added cooling when this ice, in tertrahydrofuran ring solution containing 891 mg 2-benzoyloxymethyl - 5-(3,5-dichlorophenylthio)-4-isopropylimidazole (101A), 365 mg of powdery sodium hydroxide and 118 mg of tetrabutylammonium bromide. Then the temperature was raised to room temperature and again was added powdered sodium hydroxide for alkalizing. After 5 hours the mixture was diluted with water, was extracted with diethyl ether, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. The residue was purified by chromatography on silica gel (hexane:ethyl acetate = 2:1), and received 300 mg of 2-benzoyloxymethyl-5-(3,5-dichlorophenylthio)-4 - isopropyl-1-(3-(2-PIM, 2H), 3,09 (Sept., 1H), 3,97 (m, 2H), to 4.52 (s, 2H), of 4.66 (s, 2H), 6,74 (d, 2H), 6,95 (m, 1H), to 7.09 (d, 1H), 7,12 (m, 1H), 7,31 (m, 5H), 7,54 (m, 1H), 8,49 (m, 1H).

To 300 mg of 2-benzoyloxymethyl-5-(3,5-dichlorophenylthio)-4 - isopropyl-1-(3-(2-pyridyl)propyl)-imidazole was added 10 ml of ethanol and 20 ml of 36% hydrochloric acid, and the mixture was stirred for 2 hours at 90oC. After completion of the reaction the solvent drove away under reduced pressure, was added aqueous sodium bicarbonate solution and was extracted with ethyl acetate. The extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate: methanol = 10: 1) and received 127 mg of 5-(3,5-dichlorophenylthio)-4-isopropyl - 2-hydroxymethyl-1-(3-(2-pyridyl)propyl)-1H-imidazole (yield 51%).

1H-NMR (CDCl3-TMS) million D.: of 1.18 (d, J= 7,0 Hz, 6H), of 2.16 (m, 2H), 2,85 (m, 2H), 3,05 (Sept., 1H), was 4.02 (m, 2H), amounts to 4.76 (s, 2H), 6.75 in (d, 2H), 7,05-7,19 (m, 3H), 7,60 (m, 1H), 8,49 (m, 1H).

Elemental analysis (C21H23Cl2N3OS 0,3 H2O)

Calculated (%): C 57,09 H 5,38 N 9,51 Cl Of 16.05 S 7,25

Found (%): C 57,34 Lower Than The 5.37 H N 9,70 Cl 15,78 S 7,07.

In 10 ml of tetrahydrofuran was dissolved 110 mg of 5-(3,5-dichlorophenylthio)- 4-isopropyl-2-hydroxymethyl-1-(3-(2-pyridyl)propyl)-1H-imidazole, and the resulting mixture was cooled to -40ooC. After completion of the reaction the solution is kept under reduced pressure, was added aqueous sodium bicarbonate solution, extracted with ethyl acetate, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate:methanol = 10:1), resulting in a received 80 mg of the Compound 1-130 (yield 83%).

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J= 7,0 Hz, 6H), of 2.08 (m, 2H), 2,78 (m, 2H), is 3.08 (Sept., 1H), 3,97 (m, 2H), with 5.22 (s, 2H), 6,00 (width, 2H), 6,76 (d, 2H), to 7.09 (m, 3H), to 7.59 (m, 1H), 8,45 (m, 1H).

Elemental analysis (C22H24Cl2N4O2S0,3H2O)

Calculated (%): C 54,50 H 5,11 N 11,57 Cl 14,62 S 6,61

Found (%): C 54,52 To 5.21 H N 11,78 Cl 14,51 S 6,53.

Example 131

Synthesis of 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-1-(6-oxo - 1,6-dihydropyridines-3-ylmethyl)-4-isopropyl-1H-imidazole (Compound 1-131)

In 5 ml of methylene chloride was dissolved 375 mg of 2-methoxy-5 - hydroxymethylpropane, after which the mixture was cooled to -40oC in a bath of dry ice was added 209 μl of thienylboronic. Then the mixture was left naked is issued under reduced pressure. The residue was added under ice cooling in tertrahydrofuran ring solution containing 1179 mg 2-benzoyloxymethyl-5-(3,5-dichlorophenylthio)- 4-isopropyl-1H-imidazole (101A), 215 mg of powdery sodium hydroxide and 87 mg of tetrabutylammonium bromide. Then the temperature of the mixture was raised to room temperature and was again added powdered sodium hydroxide for alkalizing. After 5 hours the mixture was diluted with water, was extracted with diethyl ether, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. The residue was purified by chromatography on silica gel (methylene chloride:ethyl acetate = 4:1), and resulted from 290 mg of 2-benzoyloxymethyl-5-(3,5-dichlorophenylthio)-4 - isopropyl-1-(2-methoxypyridine-5-ylmethyl)-1H-imidazole (a) (yield 19%).

1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, 6H), to 3.09 (Sept., 1H), 3,83 (s, 3H), 4,58 (s, 2H), 4,70 (s, 2H), to 5.08 (s, 2H), 6,46 (d, 1H), 6,54 (d, 2H), 6,99 (m, 1H), 7.18 in~7,40 (m, 6H), 7,88 (d, 1H).

To a solution of 83 mg of potassium iodide in acetonitrile was added under ice cooling and stirring 64 μl of tributyltinchloride. The resulting mixture was left to heat for 10 minutes, after which was added 150 mg of 2-benzoyloxymethyl-5-(3,5-dichlorophenylthio)-1- (2-methoxypyridine-5-ylmethyl)-4-isopropyl-1H-imidazole, and the mixture p is solution of sodium bicarbonate, were extracted with ethyl acetate, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate:methanol = 10:1) and was obtained 50 mg of 2-benzoyloxymethyl-5-(3,5 - dichlorophenylthio)-1-(6-oxo-1,6-dihydropyridines-3-ylmethyl)-4-isopropyl - 1H-imidazole (a) (yield 34%).

1H-NMR (CDCl3-TMS) million D.: of 1.30 (d, J = 7 Hz, 6H), 3,12 (Sept., 1H) and 4.65 (s, 2H), amounts to 4.76 (s, 2H), 4.95 points (s, 2H), 6.35mm (d, 1H), 6,66 (d, J= 2.0 Hz, 2H), 7,05 (d, J= 2.0 Hz, 1H), was 7.08 (d, 1H), 7.23 percent~7,46 (m, 6H).

In a mixture of 5 ml ethanol and 10 ml of 36% hydrochloric acid was dissolved 50 mg of 2-benzoyloxymethyl-5-(3,5-dichlorophenylthio)-1-(6-oxo-1,6 - dihydropyridines-3-ylmethyl)-4-isopropyl-1H-imidazole, and the mixture was stirred 2 hours at 90oC. After completion of the reaction the solvent drove away under reduced pressure. It was further added an aqueous solution of sodium bicarbonate, the mixture was extracted with ethyl acetate, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. The crystals were washed with diethyl ether, filtered and received 10 mg of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl - 1-(6-oxo-1,6-dihydropyridines-3-ylmethyl] -4-isopropyl-1H-imidazole (116A) (yield 24%), pl. 220oC.

1H-NMR (CD3OD-TMS) million D.: J= 9,0 Hz, 1H).

Elemental analysis (C19H19Cl2N3O2S million D.; 1,22 (d, J= 7,0 Hz, 6H), 3,10 (Sept., 1H), 5,13 (s, 2H), 5,27 (s, 2H), 6.35mm (d, J= 9.4 Hz, 1H), to 6.67 (d, J = 1.6 Hz, 2H), 7,14 (d, J= 1.6 Hz, 1H), 7,18 (d, J= 1.8 Hz, 1H), was 7.36 (d, J= 9.4 Hz, 1H).

Example 132

Synthesis of 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-1-(2-oxo - 1,2-dihydropyridines-3-ylmethyl)-4-isopropyl-1H-imidazole (Compound 1-132)

In 15 ml of methylene chloride was dissolved 720 mg of 2-methoxy-3 - hydroxymethylpropane, and the resulting mixture was cooled to -40oC in the bath with dry ice, and then added 802 μl of thienylboronic. The resulting mixture was left for 10 minutes to heat, after which the mixture is stirred at 60oC. After 30 minutes the mixture was cooled and the solvent is kept at reduced pressure. The residue was added under ice cooling, to tertrahydrofuran ring solution containing 1264 mg 2-benzoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H - imidazole (101A), 517 mg of powdery sodium hydroxide and 167 mg of tetrabutylammonium bromide. Then the temperature of the mixture was raised to room temperature, and again was added powdered sodium hydroxide for alkalizing. After 5 hours the mixture was diluted with water, extracted with ethyl acetate, the extract was dried with sodium sulfate, and dissolve the tat = 2:1) and was obtained 1.4 g of 2 - benzoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(2-methoxypyridine-3-ylmethyl)-1H-imidazole. This compound was dissolved in acetonitrile, then added 2.2 g of potassium iodide, and then stirring under ice cooling, was added 1.7 ml of tributyltinchloride. The resulting mixture was left to warm up, and then, after 10 minutes, stirred by heating at 60oC. After 1 hour the solution is kept under reduced pressure, was added an aqueous solution of sodium bicarbonate, the mixture was extracted with ethyl acetate, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. The residue was purified by chromatography (ethyl acetate) on silica gel, resulting in a received 590 mg of 2-benzoyloxymethyl - 5-(3,5-dichlorophenylthio)-1-(2-oxo-1,2-dihydropyridines-3-ylmethyl)-4 - isopropyl-1H-imidazole (115b) (yield 38%).

1H-NMR (CDCl3-TMS) million D.: of 1.29 (d, J= 6.6 Hz, 6H), 3.15 in (Sept., 1H), a 4.53 (s, 2H), to 4.73 (s, 2H), 5,09 (s, 2H), 5,97 (m, 1H), of 6.68 (m, 1H), of 6.71 (d, J= 1.6 Hz, 2H), 7,01 (d, J= 2.0 Hz, 1H), 7,11 (m, 1H), 7,26 (m, 5H).

Elemental analysis (C26H25Cl2N3O2S0,6H2O)

Calculated (%): C 59,45 H 5,03 N 8,00 Cl 13,50 S 6,10

Found (%): C 59,79 H 5,13 N 8,29 Cl Of 13.05 S 6,16.

In a mixture of 15 ml of ethanol and 20 ml of 36% hydrochloric acid was dissolved 590 mg of 2-benzoyloxymethyl-5-(3,5-dichlorophenylthio)-(2-oxo-1,2 - dihydropyridines-3-ylmethyl)-4-isopropyl-1H-imidazole (115b), and propanganda pressure. To the residue was added an aqueous solution of sodium bicarbonate, then extracted with ethyl acetate, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. The crystals were washed with diethyl ether and filtered, resulting in a received 264 mg of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-1-(2(1H)-pyridone-3-ylmethyl)- 4-isopropyl-1H-imidazole (116b) (yield 54%). So pl. 244oC.

1H-NMR (CD3OD-TMS) million D.: of 1.23 (d, J= 7,0 Hz, 6H), 3,11 (Sept., 1H), a 4.83 (s, 2H), by 5.18 (s, 2H), 6,01 (m, 1H), of 6.71 (d, 2H), 7,05-7,20 (m, 3H).

Elemental analysis (C19H19Cl2N3O2S0,2H2O)

Calculated (%): C 53,33 H 4,57 N 9,82 Cl 16,57 S 7,49

Found (%): C 53,62 H 4,62 N 9,79 Cl 16.28 Per S 7,60.

In 20 ml of tetrahydrofuran was dissolved 200 mg of 5-(3,5-dichlorophenylthio)- 2-hydroxymethyl-1-(2-oxo-1,2-dihydropyridines-3-ylmethyl)-4-isopropyl - 1H-imidazole (116b), and the resulting mixture was cooled to -40oC. Then, with stirring, was added 84 μl trichlorotriazine, after which the mixture was left at room temperature to complete the reaction and stirred for 30 minutes. Then added 500 μl of triethylamine, 5 ml of water and 5 ml of methanol, and the mixture is stirred at 70oC for 1 hour. After completion of the reaction the solution is kept under reduced davleniam sodium, and the solvent is kept at reduced pressure. The crystals were washed with diethyl ether and filtered, resulting in a received 177 mg of the Compound 1-132 (yield 80%). So pl. 214oC.

1H-NMR (CD3OD-TMS) million D.: of 1.23 (d, J=7,0 Hz, 6H), 3,13 (Sept., 1H), 5,17 (s, 2H), 5,33 (s, 2H), of 5.99 (m, 1H), of 6.71 (d, J= 2.0 Hz, 2H), 7,00 (m, 1H), 7,11 (d, J= 2.0 Hz, 1H), 7,14 (m, 1H).

Example 133

Synthesis of 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl - 1-(2-methylpyridin-3-ylmethyl)-1H-imidazole (Compound 1-133)

In 10 ml of methylene chloride was dissolved 463 mg of 2-methyl-3 - hydroxymethylpropane and the resulting solution was cooled to -40oC in a bath of dry ice was added 582 μl of thienylboronic. After that, the mixture was left to warm up, and after 10 minutes it was stirred at 60oC. After 30 minutes the mixture was cooled and evaporated under reduced pressure. Under ice cooling, the residue was added to tertrahydrofuran ring solution containing 918 mg of 2-benzoyloxymethyl - 5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole (101A), 376 mg of powdery sodium hydroxide and 121 mg of tetrabutylammonium bromide. Then the temperature of the mixture was raised to room temperature, and again was added powdered sodium hydroxide for alkalizing mixture. After 5 hours the mixture was diluted VM pressure. The residue was purified by chromatography on silica gel (methylene chloride:ethyl acetate = 5:1) and received in the 609 mg 2-benzoyloxymethyl-5-(3,5 - dichlorophenylthio)-4-isopropyl-1-(2-methyl-3-pyridin-3-ylmethyl)-1H - imidazole (118a) (yield 53%).

1H-NMR (CDCl3-TMS) million D.: 1,32 (d, J=6.8 Hz, 6H), 2,48 (s, 3H), 3,17 (Sept. , 1H), 4,90 (s, 2H), 4,58 (s, 2H), 5,12 (s, 2H), 6,62 (m, 1H), of 6.68 (m, 2H), 6.90 to (m, 1H), 7,00 (m, 1H), 7,15 (m, 2H), 7,26 (m, 3H), of 8.28 (m, 1H).

Elemental analysis (C27H27Cl2N3OS 0,2 H2O)

Calculated (%): C 62,83 H 5,35 N 8,14 Cl 13,74 S 6,21

Found (%): C 62,59 H 5,47 N 7,89 Cl Of 13.27 S 6,03

In a mixture of 15 ml of ethanol and 20 ml of 36% hydrochloric acid was dissolved 609 mg 2-benzoyloxymethyl-5-(3,5-dichlorophenylthio)-4 - isopropyl-1-(2-methylpyridin-3-ylmethyl)-1H-imidazole (118a), and the mixture was stirred 3 hours at 90oC. After completion of the reaction the solvent drove away under reduced pressure. It was further added an aqueous solution of sodium bicarbonate, the mixture was extracted with ethyl acetate, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. The crystals were washed with diethyl ether and filtered, resulting in a received 500 mg of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl-1-(2 - methylpyridin-3-ylmethyl)-1H-imidazole (a) (yield 99%). So pl. 136), 6,69 (m, 2H), 6,94 (m, 1H), 7,02 (m, 1H), 8,29 (m, 1H).

Elemental analysis (C20H21Cl2N3OS 0,2 H2O)

Calculated (%): C 56,39 H 5,06 N 9,86 Cl 16,65 S 7,53

Found (%): C 56,34 of 5.05 H N 9,83 Cl 16,79 S 7,56

In 20 ml of tetrahydrofuran was dissolved 405 mg of 5-(3,5-dichlorophenylthio)- 2-hydroxymethyl-4-isopropyl-1-(2-methylpyridin-3-ylmethyl)-1H-imidazole (a), and the resulting mixture was cooled to -40oC. Then, with stirring, was added 171 μl trichlorotriazine, after which the mixture was left at room temperature to complete the reaction, and the mixture is stirred for 30 minutes. Next was added 200 μl of triethylamine, 5 ml of water and 10 ml of methanol, and the mixture is stirred 2 hours at 70oC. After completion of the reaction the solution is kept under reduced pressure, was added an aqueous solution of sodium bicarbonate, the mixture was extracted with ethyl acetate, the extract was dried with sodium sulfate, and the solvent is kept at reduced pressure. The crystals were washed with diethyl ether, filtered and received 400 mg of the Compound 1-133 (yield 90%). So pl. 127oC.

1H-NMR (CDCl3-TMS) million D.: 1,32 (d, J= 7,0 Hz, 6H), of 2.56 (s, 3H), 3,19 (Sept., 1H), 4,48 (width, 2H), by 5.18 (s, 2H), 5,20 (s, 2H), of 6.52 (m, 1H), 6,72 (m, 2H), 6,95 (m, 1H), 7,05 (m, 1H), 8,31 (m, 1H).

Example 134

Synthesis of 1-(2-carbamoylethyl)-2-the acetonitrile was dissolved 5.0 g (12.3 mmol) imidazolones connection (101A), and then was added 3.4 g (25 mmol) of potassium carbonate and 3.1 g (to 18.6 mmol) ethylbromoacetate, and the mixture is stirred for 8 hours by heating at 60oC. Then the mixture was diluted with water with ice and was extracted with ethyl acetate. The extract was washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:n-hexane = 1:2) and was obtained 5.6 g of 2-[2-benzoyloxymethyl-5-(3,5-dichlorophenylthio)- 4-isopropyl-1H-imidazol-1-yl)]ethyl acetate (118b) as an oily product (yield 92%).

1H-NMR (CDCl3-TMS) million D.: 1,10 (t, J = 7.2 Hz, 3H), 1.27mm (d, J = 6.8 Hz, 6H), 3,11 (Sept., 1H), 3,95 (sq, J = 7.2 Hz, 2H), 4,50 (s, 2H), 4,70 (s, 2H), amounts to 4.76 (s, 2H), 6,83 (m, 2H), 7,10 (m, 1H), 7,30 (m, 5H).

In 30 ml of anhydrous diethyl ether was dissolved 3.0 g (6.0 mmol) of the ether compound (118b), and then under ice cooling was added 230 mg (6.0 mmol) of lithium aluminum hydride. The mixture is stirred for 15 minutes at room temperature, and then added water. The resulting mixture was extracted with ethyl acetate, the extract washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate),NELTI)-4-isopropyl-1H-imidazol-1-yl] ethanol (s) in the form of crystals (yield 79%). So pl. 78-80oC.

1H-NMR (CDCl3-TMS) million D.: a 1.25 (t, J = 6.8 Hz, 6H), to 2.55 (t, J = 5.4 Hz, 1H), 3,10 (Sept., 1H), and 3.72 (m, 2H), 4.09 to (t, J = 5.0 Hz, 2H), br4.61 (s, 2H), 4.72 in (s, 2H), 6,78 (m, 2H), 7,11 (m, 5H), 7,35 (m, 5H).

Elemental analysis (C22H24Cl2N2O2S)

Calculated (%): C 58,54 are 5.36 H Cl 15,71 N 6,21 S 7,10

Found (%): C 58,46 Are 5.36 H Cl 15,57 N 6,23 S 7,29.

After adding 18 ml of concentrated hydrochloric acid to 1.8 g (4.0 mmol) of the alcohol compound (s) the mixture is stirred for 7 hours heating at 110oC. the mixture is Then cooled, neutralized with sodium bicarbonate and was extracted with ethyl acetate. The extract was washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate), and as a result received 960 mg of 2-(5-(3,5-dichlorophenylthio)-2-hydroxymethyl-4-isopropyl - 1H-imidazol-1-yl) ethanol (119b) as an oily product (yield 67%).

1H-NMR (CDCl3-TMS) million D.: of 1.18 (d, J = 7.2 Hz, 6H), is 3.08 (Sept., 1H), 3,76 (t, J = 5.0 Hz, 2H), 4,17 (t, J = 5.0 Hz, 2H), 4,67 (s, 2H), 4,90 (Shir. , 1H), 6,60 (width, 1H), 6,80-7,13 (m, 1H).

In 9 ml of anhydrous tetrahydrofuran was dissolved 910 mg (2.5 mmol) delovogo connection (119b), after which the mixture was cooled to-Noi temperature and stirred for 1 hour. Then added 4 ml of water and 2 ml of tetraethylene, and the mixture is stirred 3 hours at 50oC. the resulting mixture was diluted with water, extracted with ethyl acetate, the extract washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel and then recrystallized from a mixture of ethyl acetate-n-hexane, resulting in received 900 mg of Compounds 1-134 in the form of crystals (yield 80%). So pl. 159-161oC.

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J=7,0 Hz, 6H), 3,10 (Sept., 1H), 4,22 (m, 4H), 4,74 (width, 2H), 4,93 (width, 2H), 5,27 (s, 2H), to 6.80 (m, 2H), 7,12 (m, 1H).

Example 135

Synthesis of 2-[5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol - 2-yl] ndimethylacetamide (Compound 1-135)

In a mixture of 46 ml of anhydrous methanol and 86 ml of anhydrous ether was dissolved 8.6 g (2.5 mmol) cyanomethylene connection (s), and under ice cooling, and the mixture was purged with chlorocarbon before saturation. Then the mixture was stirred for 15 minutes at 4oC and upon cooling, ice water was gradually added with ice. After the reaction mixture was poured into a cooled aqueous solution of sodium bicarbonate and was extracted with diethyl ether. The extract was washed with water, dried anhydrous is silica gel. From the faction, elyuirovaniya a mixture of 3% methanol/methylene chloride, got 7,17 g of the ester compound (yield 76%), and from the faction, elyuirovaniya a mixture of 10% methanol/methylene chloride, was obtained 1.85 g of Compound 1-135 in the form of crystals (yield 21%). So pl. 164-166oC.

1H-NMR (CDCl3-TMS) million D.: of 1.23 (d, J= 6.6 Hz, 6H), of 3.12 (Sept, 1H), 3,41 (s, 3H), of 3.75 (s, 2H), 5,90 (width, 1H), 6,80 (m, 2H), 7,12 (m, 1H), 7,93 (width, 1H).

IR (Nujol") : 3336, 3136, 3070, 1673 cm-1< / BR>
Elemental analysis (C15H17Cl2N3OS)

Calculated (%): C 50,19 H 4,78 Cl 19,79 N 11,73 S 8,95

Found (%): C 50, 20mm H 4,82 Cl 19,65 N 11,66 S 9,03.

Example 136

Synthesis of 2-(2-benzyloxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl - 1-methyl-1H-imidazole (Compound 1-136)

In 20 ml of anhydrous methylene chloride was dissolved 3,0 g (11.9 mmol) of benzyl-2,2,2-trichloroacetimidate, and then was added molecular sieve 3A. Then at room temperature was added 2.7 g (7.8 mmol) of the alcohol compound (e). After 5 minutes was added 5 ml of anhydrous methylenechloride solution containing 1.7 g of a complex of boron TRIFLUORIDE and diethyl ether. The resulting mixture was left for 40 minutes at room temperature to complete the reaction and poured into a cooled aqueous solution of sodium bicarbonate. The mixture was extreamely under reduced pressure. The residue was separated into fractions using column chromatography on silica gel (ethyl acetate:n-hexane = 1:1), and received of 2.06 g of Compound 1-136 in the form of crystals (yield 61%). So pl. 101-103oC.

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J=7,0 Hz, 6H), of 3.07 (t, J= 6.2 Hz, 2H), 3,10 (Sept., 1H), 3.46 in (s, 3H), of 3.84 (t, J= 6.2 Hz, 2H), 4,51 (s, 2H), to 6.80 (m, 2H), to 7.09 (m, 1H), 7,28 (m, 5H).

Elemental analysis (C15H20Cl2N2OS)

Calculated (%): C 60,69 H 5,56 Cl 16.28 Per to 6.43 N S OF 7.36

Found (%): C 60,67 H 5,70 Cl 15,98 N 6,32 S 7,16.

Example 137

Synthesis of 2-(2-carbamoylethyl)-5-(3,5-dichlorophenylthio)-1-ethyl - 4-isopropyl-1H-imidazole (Compound 1-137)

In 20 ml of anhydrous acetonitrile was dissolved 4.0 g (9.5 mmol) of the Compound 1-136, then added 1.4 g (19 mmol) of lithium carbonate and 1.8 g (11.7 mmol) of diethylsulfate, and the resulting mixture was left for 9 hours at 70oC to complete the reaction. Next, the mixture was diluted with ice water and was extracted with ethyl acetate. The extract was washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:n-hexane 1:1), and received a 3.9 g of 2-(2-benzyloxyethyl-5-(3,5-dichlorophenylthio)-1-ethyl - 4-isopropyl-1H-imidazole (a) mA inputs3,06 (m, 3H), 3,91 (m, 4H), to 4.52 (s, 2H), for 6.81 (m, 2H), to 7.09 (m, 1H), 7,28 (m, 5H).

In 16 ml of concentrated hydrochloric acid was dissolved 3.8 g (8.5 mmol) of benzyl compounds (a), and the resulting mixture was heated for 2 hours at 100oC. After cooling, the mixture was neutralized with sodium bicarbonate, extracted with ethyl acetate, and the extract was washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (1% methanol:ethyl acetate), washed with n-hexane and filtered, resulting in received to 2.57 g of 2-[5- (3,5-dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl] ethanol (123A) as crystals (yield 85%). So pl. 80-81oC.

1H-NMR (CDCl3-TMS) million D.: of 1.16 (t, J= 7.4 Hz, 3H), 1,22 (d, J=6.6 Hz, 6H), 2,87 (t, J= 5.4 Hz, 2H), 3,06 (Sept, 1H), a 3.87 (sq, J= 7,4 Hz, 2H), 4.09 to (sq, J= 5.4 Hz, 2H), 4,91 (m, 1H), PC 6.82 (m, 2H), 7,11 (m, 1H).

Elemental analysis (C16H20Cl2N2OS)

Calculated (%): C 53,48 H 5,61 Cl 19,73 N 7,80 S 8,92

Found (%): C 53,48 H 5,61 Cl 19,73 N 7,80 S 8,92

In 15 ml of anhydrous tetrahydrofuran was dissolved 1.5 g (4.2 mmol) of the alcohol compound (123A), after which the resulting mixture was cooled to -30oC and was added 1.2 g (6.4 mmol) trichloroacetimidate. After 5 minutes, see the Extract was washed with water, and ethyl acetate drove away. To the residue was added 15 ml of methanol, 0.26 g of triethylamine and 0.72 ml of water, and the resulting mixture was heated for half an hour at 50oC. the mixture is Then diluted with ice water and was extracted with ethyl acetate. The extract was washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (2% methanol: ethyl acetate) and recrystallized from a mixture of ethyl acetate and n-hexane, which was given 1.5 g of Compound 1-137 in the form of crystals (yield 89%). So pl. 161-162oC.

1H-NMR (CDCl3-TMS) million D.: of 1.20 (t, J=7.4 Hz, 3H), of 1.23 (d, J= 7,0 Hz, 6H), of 3.07 (Sept., 1H), 3,10 (t, J= 7,0 Hz, 2H), 3,92 (sq, J= 7,4 Hz, 2H), 4,47 (t, J=7,0 Hz, 2H), 4,67 (width, 2H), to 6.80 (m, 2H), 7,11 (m, 1H).

Elemental analysis (C17H21Cl2N3O2S)

Calculated (%): C 50,75 H 5,26 Cl 17,62 N 10,44 S 7,97

Found (%): C 50,79 To 5.21 H Cl 17,33 N 10,36 S 7,98.

Example 138

Synthesis of 2-(2-carbamoylethyl)-5-(3,5-dichlorophenylthio)-4 - isopropyl-1-(pyridine-4-yl)methyl-1H-imidazole (Compound 1-138)

In 20 ml of tetrahydrofuran was dissolved 2.0 g (4.7 mmol) imidazolones connection (Connection 1-136) and then was added to 1.9 ml of 40% aqueous sodium hydroxide solution, 100 mg of bromide n-t 6 hours at 50oC. Then the mixture was extracted with ethyl acetate, the extract washed with water, dried with anhydrous sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (2% methanol:ethyl acetate), resulting in a 2.4 g of 4-[2-(2-benzyloxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-1-ylmethyl] pyridine (122b) as an oily product (yield 98%).

1H-NMR (CDCl3-TMS) million D.: of 1.30 (d, J = 7.2 Hz, 6H), to 2.99 (t, J = 6.0 Hz, 2H), and 3.16 (Sept., 1H), 3,84 (t, J = 6.0 Hz, 2H), 4,47 (s, 2H), 5,16 (s, 2H), 6,69 (m, 2H), 6,76 (d, J= 6.0 Hz, 2H), 7,01 (m, 1H), 7,22 (m, 5H), of 8.37 (d, J = 6.0 Hz, 2H).

In 12 ml of concentrated hydrochloric acid was dissolved 2.3 g (4.5 mmol) of benzyl compounds (122b), and the resulting mixture was heated for 4 hours at 100oC. Then the mixture was neutralized with sodium bicarbonate and was extracted with ethyl acetate. The extract was washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (7% methanol/ethyl acetate) and received 1.28 g 2-[5-(3, 5-dichlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)-1H - imidazol-2-yl] ethanol (123b) in the form of crystals (yield 67%). So pl. 121-122oC.

1H-NMR (CDCl3-TMS) million D.:1H), 8,48 (d, J = 4,6 Hz, 2H).

Elemental analysis (C20H21Cl2N3OS)

Calculated (%): C 56,87 H 5,01 Cl 16,79 N 9,95 S TO 7.59,

Found (%): C 56,69 H 5,02 Cl 16,70 N 8,89 S 7,41

In 10 ml of anhydrous tetrahydrofuran was dissolved 1.0 g of 12.4 mmol) of the alcohol compound (123b), after which the mixture was cooled to -20oC and was added 540 mg (2.9 mmol) trichloroacetimidate. After 3 minutes, the mixture was heated to 0oC and stirred for 10 minutes. Then added 4 ml of water and 2 ml of triethylamine, and the resulting mixture was heated at 50oC for 2 hours. Next, the mixture was diluted with ice water and was extracted with ethyl acetate, and the extract was washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (10% methanol/ethyl acetate) and recrystallized from ethyl acetate, resulting in a received 930 mg of the Compound 1-138 in the form of crystals (yield 85%). So pl. 189-191oC.

1H-NMR (CDCl3-TMS) million D.: of 1.28 (d, J=7,0 Hz, 6H), 3,03 (t, J= 6.6 Hz, 2H), 3,14 (Sept. , 1H), 4,42 (t, J= 6.6 Hz, 2H), 4,63 (width, 2H), 5,13 (s, 2H), of 6.71 (m, 2H), for 6.81 (d, J= 6.0 Hz, 2H), 7,05 (m, 1H), 8,48 (d, J= 6.0 Hz, 2H).

Elemental analysis (C21H22Cl2N4O2S)

Calculated SIL)-5-(3,5-dichlorophenylthio)-2 - hydroxyethyl-4-isopropyl-1H-imidazole (Compound 1-139)

In 10 ml of tetrahydrofuran was dissolved 1,05 mg (2.5 mmol) of 2-(2-benzyloxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H - imidazole (Compound 1-136), after which was added 220 mg (5.5 mmol) of sodium hydroxide, 48 mg (0.15 mmol) of tetrabutylammonium bromide and 594 mg (2,75 mmol) nitrobenzylamine, stirring at room temperature, and the mixture was left for 3 hours to undergo reaction. Next, the reaction mixture is kept under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with water, dried and the solvent drove away. The residue was purified by column chromatography on silica gel (ethyl acetate:chloroform = 1:9), and obtained 1.3 g (93%) of 2-(2-benzyloxyethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-p - nitrobenzyl-1H-imidazole (125) in the form of an oily product.

1H-NMR (CDCl3that ) million D.: 1,32 (d, J=7 Hz, 6H), to 3.0 - 3.2 (m, 1H), 3,03 (t, J= 5.8 Hz, 2H), a 3.87 (t, J= 5.8 Hz, 2H), 4,47 (s, 2H), 5,24 (s, 2H), is 6.61 (d, J= 2 Hz, 2H), 6,98 (t, J=2 Hz, 1H), 7,0 (d, J= 9 Hz, 2H), 7,2~to 7.3 (m, 5H), to 7.93 (d, J=9 Hz, 2H).

In 5 ml of concentrated hydrochloric acid was dissolved 1.3 g (2.34 mmol) of the benzyl compound (125), and the resulting mixture was heated under reflux for 4 hours. To the reaction mixture were added saturated aqueous solution of sodium bicarbonate and extrage the om and was led, the result that was obtained 5-(3,5 - dichlorophenylthio)-2-(2-hydroxyethyl)-4-isopropyl-1-p-nitrobenzyl-1H - imidazole (a). So pl. 169-171oC.

1H-NMR (CDCl3) million D.: of 1.27 (d, J= 4.4 Hz, 6H), 2,84 (t, 2H), 3,1~3,2 (m, 1H), 4,1 (t, 2H), 4,45 (width, 1H), 5,17 (s, 2H), only 6.64 (d, J= 1.2 Hz, 2H), 7,00 (t, J= 1.2 Hz, 1H)? 7.04 baby mortality (d, J= 5.8 Hz, 1H), of 8.06 (d, J= 5.8 Hz, 1H).

Elemental analysis (C21H21N3Cl2O3S)

Calculated (%): C 54,08 H 4,54 N 9,01 S 6,87

Found (%): C 54,05 H 4,59 N 8,84 S 6,70.

In 10 ml of ethyl acetate was dissolved 124 mg (0.26 mmol) nitrobenzylamine connection (a) was added at room temperature to 120 mg of sulfur platinum on coal. Then, with stirring, for 7 hours was injected gas H2and the resulting mixture is appropriately processed. That is, the reaction mixture was filtered through celite under reduced pressure, and the filtrate drove away. The residue was purified by column chromatography on silica gel (ethyl acetate), and the obtained oily product was treated with ether for crystallization, resulting in the received Connection 1-139 (yield 33%). So pl. 142-145oC.

1H-NMR (CDCl3) million D.: of 1.23 (d, J= 7,0 Hz, 6H), 2,85 (t, J= 5.4 Hz, 2H), 3,0-3,2 (m, 1H), a 4.03 (t, J= 5.4 Hz, 2H), 4,94 (s, 2H), 6,47 (d, J= 8,2 Hz, 2H), 6,66-of 6.73 (m, 4H), 7,02 (t, 1H).

Elementry H 5,27 N 9,37 S 7,09 Cl 15,81

Example 140

Synthesis of 1-(p-aminobenzyl)-2-(2-carbamoylethyl)-5-(3,5 - dichlorophenylthio)-4-isopropyl-1H-imidazole (Compound 1-140)

In 5 ml of tetrahydrofuran was dissolved 467 mg (1 mmol) 5-(3,5-dichlorophenylthio)-2-(2-hydroxyethyl)-4-isopropyl-1-p - nitrobenzyl-1H-imidazole (a), then, while stirring and cooling in a bath at -20oC was added to 0.23 g (1.2 mmol) trichloroacetimidate. Then the bath was removed and the mixture was left for 2 hours to undergo reaction. Next, to the reaction mixture were added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with methylene chloride. The extract was washed with water, dried and the solvent is kept in the result as the remainder received trichlorocarbanilide connection, which was suitable for use in the next reaction. This intermediate compound was dissolved in 10 ml of aqueous methanol (10%), then stirring at room temperature, was added 0.2 ml of triethylamine, and the mixture was stirred for 3 hours, heating at 50oC, and accordingly processed. If the deposited crystals, the mixture was directly filtered. If the crystals were not deposited, then the reaction mixture was added saturated water and drained, the solvent is kept off, and the residue was purified by column chromatography on silica gel (ethyl acetate), resulting in a received 2-(2-carbamoylethyl)-5-(3,5-dichlorophenylthio)-4 - isopropyl-1-(p-nitrobenzyl)-1H-imidazole (a) as an oily product (yield 98%).

1H-NMR (CDCl3) million D.: of 1.27 (d, J=7 Hz, 6H), is 3.08 (t, J=7 Hz, 2H), 3,0~3,2 (m, 1H), 4,43 (t, J=7 Hz, 2H), 5,23

(s, 2H), only 6.64 (d, J=2 Hz, 2H), 7,01 (t, J=2 Hz, 1H), 7,05 (d, J= 8.6 Hz, 2H), 8,07 (d, J= 8.6 Hz, 2H).

In 10 ml of ethyl acetate was dissolved 220 mg (0.43 mmol) of 2-(2-carbamoylethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1- (p-nitrobenzyl)-1H-imidazole (a), and then at room temperature was added 120 mg of sulfur platinum on coal. After that, stirring, for 7 hours was introduced hydrogen gas, and the mixture was processed. The reaction mixture was filtered through celite under reduced pressure, and the filtrate drove away. The oily residue was treated with ether for crystallization, and received the Connection 1-140 (yield 95%).

1H-NMR (CDCl3) million D.: 1,25 (DD, J=7 Hz, 2 Hz, 6H), 3,0~3,2 (m, 3H), 4,3~ was 4.42 (m, 2H), 4,6 (width, 2H), 4,99, of 5.05 (2, 2H), 6,45~6,5 (m, 1H), 6,65~of 6.75 (m, 2H), 7,01 (t, J=2 Hz, 1H).

Example 141

Synthesis of 1-(m-aminobenzyl)-5-(3,5-dichlorophenylthio)-2-hydroxyethyl - 4-isopropyl-1H-imidazole (Compound 1-141)

In 10 ml of tetr ulali 220 mg (5.5 mmol) of sodium hydroxide, 48 mg (0.15 mmol) of tetrabutylammonium bromide and 594 mg (2,75 mmol) nitrobenzotrifluoride, and the resulting mixture was left for 3 hours, heating at 60oC to complete the reaction, and then appropriately processed. The reaction mixture is kept under reduced pressure, the residue was extracted with ethyl acetate, the extract was washed with water and dried, and the solvent drove away. The residue was purified by column chromatography on silica gel (ethyl acetate:chloroform = 1:9), which was obtained 1.26 g of 2-(2-benzyloxyethyl)-5- (3,5-dichlorophenylthio)-4-isopropyl-1-n-nitrobenzyl-1H-imidazole (125b) as an oily product (yield 90%).

So pl. 119-122oC.

1H-NMR (CDCl3) million D.: of 1.29 (d, J=7 Hz, 6H), 3,0~3,2 (m, 1H), of 3.07 (t, J=5.6 Hz, 2H), 3,88 (t, J= 5.6 Hz, 2H), 4,48 (s, 2H, in), 5.25 (s, 2H), 6,59 (d, J= 1.8 Hz, 2H), 6,95 (t, J= 1.8 Hz, 1H), 7,81 (s, 1H), of 7.97 (d, J=6 Hz, 1H).

5-(3,5-Dichlorophenylthio)-2-(2-hydroxyethyl)-4-isopropyl-1-m - nitrobenzyl-1H-imidazole (126b) was obtained from compound (125b) the method described in example 139 for connection (a). So pl. 85-88oC.

1H-NMR (CDCl3) million D.: of 1.28 (d,J= 6.8 Hz, 6H), 2,87 (so J= 4,8 Hz, 2H), 3,1~3,2 (m, 1H), 4.09 to (t, J= 4,8 Hz, 2H), 5,17 (s, 2H), of 6.20 (d, J= 1.6 Hz, 2H), 6,72 (d, J= 1.6 Hz, 1H), 6,98~of 6.99 (m, 1H), 7,1~to 7.15 (m, 1H), of 7.36~ 7,42 (m, 2H), 7,83 (width, s, 1H), 7,98~8,1 (m, 1H).


Found (%): C 54,32 H 4,65 N 8,81 S 6,72 Cl 15,39.

Connection 1-141 received from (126b) by the method described in example 139 synthesis of Compound 1-139. So pl. 114-118oC.

1H-NMR (CDCl3) million D.: a 1.25 (d, J=7 Hz, 2H), 2,82 (t, J=5.6 Hz, 2H), 3,0~ 3,2 (m, 1H), was 4.02 (t, J= 5.6 Hz, 2H), 4,96 (s, 2H), 6,13 (s, 1H), and 6.3 (d, 1H), 6,5 (DD, 1H), 6,72 (d, J=1.8 Hz, 2H), 7,0 (d, 1H),? 7.04 baby mortality (t, J= 1.8 Hz, 1H).

Example 142

Synthesis of 1-(m-aminobenzyl)-2-(2-carbamoylethyl)-5-(3,5 - dichlorophenylthio)-4-isopropyl-1H-imidazole (Compound 1-142)

2-(2-Carbamoylethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl - 1-(n-nitrobenzyl)-1H-imidazole (128b) was obtained from (126b) by the method described in example 140 synthesis of compound (a). Yield 83%. So pl. 167-169oC.

1H-NMR (CDCl3) million D.: of 1.28 (d, J= 7 Hz, 6H), of 3.12 (t, J=5.8 Hz, 2H), 3,0-3,2 (m, 1H), 4,47 (t, J= 5.8 Hz, 2H), 4,63 (width, 2H), 5,23 (s, 2H), is 6.61 (d, J= 2 Hz, 2H), 6.97 (t, J=2 Hz, 1H), 7,40 (t, J= 8,2 Hz, 1H), 7,81 (width,1H), 8,02 (DD, 1H).

Elemental analysis (C22H22N4Cl2O4S0,2H2O)

Calculated (%): C 51,50 H 4,40 N 10,92 6,25 S Cl 13,92

Found (%): C 51,28 H 4,40 N 10,88 S 6,27 Cl 13,72.

Connection 1-142 was obtained from the compound (128b) by the method described in example 140 synthesis of Compound 1-140. So pl. 172-176oC.

1H-NMR (CDCl3) million D. : of 1.27 (d, J=7 Hz, 6H), to 3.0-3.2 (m, 3H), 3,6 (Shir. , 2H is entry analysis: (C22H24N4Cl2OS 0,8 H2O)

Calculated (%): C 53,51 H 5,23 N 11,35 S OF 6.49

Found (%): C 53,80 H A 4.86 N 11,35 S 6,48.

Example 143

Synthesis of 1-(o-aminobenzyl)-5-(3,5-dichlorophenylthio)-2-(2 - hydroxyethyl)-4-isopropyl-1H-imidazole (Compound 1-143)

2-(Benzyloxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(o - nitrobenzyl)-1H-imidazole (125C) was obtained from Compound 1-136 the method described in example 139 synthesis of compound (125). An oily substance. Yield 49%.

1H-NMR (CDCl3) million D.: 1,32 (d, J=6.6 Hz, 6H), to 2.99 (t, J= 6.2 Hz, 2H), 3,1-up 3.22 (m, 1H), 3,84 (t, J= 6.2 Hz, 2H), of 4.45 (s, 2H), to 5.58 (s, 2H), 6,4-of 6.45 (m, 1H), 6,69 (d, J= 2 Hz, 2H), 7,21 (t, J=2 Hz, 1H), of 7.95-with 8.05 (m, 1H).

5-(3,5-Dichlorophenylthio)-2-(2-hydroxyethyl)-4-isopropyl - 1-o-nitrobenzyl-1H-imidazole (s) was obtained from (125C) by the method described in example 139 synthesis (a). So PL, 104-107oC.

1H-NMR (CDCl3) million D.: of 1.30 (d, J= 6.6 Hz, 6H), 2,78 (t, J= 5.4 Hz, 2H), 3,1-3,2 (m, 1H), of 4.05 (t, J= 5.4 Hz, 2H), 5,49 (s, 2H), 6,37 (d, J= 8 Hz, 1H), 6,72 (d, J=1.8 Hz, 2H), 6,99 (t, J= 1.8 Hz, 1H), was 7.36-7,46 (m, 2H), 8,05 to 8.1 (m, 1H).

Elemental analysis (C21H21N3Cl2O3S)

Calculated (%): C 54,08 H 4,54 N 9,01 S 6,87 Cl 15,20

Found (%): C 54,01 H 4,62 N 8,92 6,80 S Cl 15,04.

Compound 1-143 received from (s) by the method described in example 139 synthesis is C, 2H), 3,0-3,2 (m, 1H), 3,55 (width, 2H), 4.00 points (t, J= 5.6 Hz, 2H), 4,91 (s, 2H), and 6.3 (d, 1H), 6,6-of 6.65 (m, 4H), 7,01-7,03 (m, 2H).

Elemental analysis (C21H23N3Cl2OS)

Calculated (%): C 57,92 H 5,33 N 9,66 S 7,35 Cl 16,07

Found (%): C 57,54 Of 5.40 H N 9,44 S 7,20 Cl 16,49.

Example 144

Synthesis of 1-(o-aminobenzyl)-2-(2-carbamoylethyl)-5-(3,5 - dichlorophenylthio)-4-isopropyl-1H-imidazole (Compound 1-144)

2-(2-Carbamoylethyl)-5-(3,5-chlorophenylthio)-4-isopropyl-1- (o-nitrobenzyl)-1H-imidazole (s) was obtained from (s) by the method described in example 140 to obtain (a). Yield 87%. So pl. 163-165oC.

1H-NMR (CDCl3) million D.: 1,31 (d, J=6.8 Hz, 6H), 3,01 (s, J= 6.2 Hz, 2H), 3,1-up 3.22 (m, 1H), 4,6 (width, 2H), to 5.56 (s, 2H), 6,4 (DD, 1H), 6,72 (d, J= 1.4 Hz, 2H), 7,01 (t, J=1.4 Hz, 1H), and 7.3-7.5 (m, 2H), 8,07 (DD, 1H).

Elemental analysis (C22H22N4Cl2O4S million D.: of 1.28 (d, J= 7 Hz, 6H), to 3.02 (t, J=6.6 Hz, 2H), 3,05 is 3.23 (m, 1H), 3,6 (width, 2H), 4,37 (t, J=6.6 Hz, 2H), 4,58 (width, 2H), equal to 4.97 (s, 2H), 6,28 (d, J=7.2 Hz, 1H), 6,6-of 6.65 (m, 2H), 6,7 (d, J= 1.8 Hz, 2H), 7,03 (t, J= 1.8 Hz, 1H).

Elemental analysis (C22H24N4Cl2O2S)

Calculated (%): C 55,12 H of 5.05 of 11.69 N S 6,09 Cl 14,79

Found (%): C 54,89 H 5,11 N 11,40 S 6,56 Cl 14,56.

Example 145

Synthesis of 2-[5-(3,5-dichlorophenylthio)-4-isopropyl-1-n-propyl - 1H-imidazol-2-yl]ethanol (Compound 1-145)

In beii ice was added 570 mg (14 mmol) of 60% sodium hydride. After 5 minutes, was added 1.75 g (of 14.2 mmol) of n-propyl bromide, and the mixture was stirred for 3 hours under heating at 50oC. the mixture was diluted with ice water, extracted with ethyl acetate, the extract washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:n-hexane = 1:1) and resulted 3,19 g 2-(2-benzyloxyethyl - 5-(3,5-dichlorophenylthio)-4-isopropyl-1-n-propyl-1H-imidazole (130A) in the form of an oily product (yield 73%).

1H-NMR (CDCl3-TMS) million doctor: or 0.83 (t, J=7.4 Hz, 3H), of 1.29 (d, J= 7,0 Hz, 6H), of 1.55 (m, 2H), 3,06 (m, 3H), 3,85 (m, 4H), 4.53-in (s, 2H), 6,79 (m, 2H), to 7.09 (m, 1H), 7,29 (m, 5H).

In 31 ml of concentrated hydrochloric acid was dissolved 3.1 g benzyloxy-connection (130A), and the mixture was stirred by heating at 110oC for 2.5 hours. After cooling, the mixture was neutralized with sodium bicarbonate and was extracted with ethyl acetate. The extract was washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate) and recrystallized from a mixture of ethyl acetate and n-hexane, H-NMR (CDCl3-TMS) million D.: 0,86 (t, J= 7,6 Hz, 3H), 1,21 (d, J= 7,0 Hz, 6H), 1.57 in (m, 2H), 2,87 (t, J= 5.4 Hz), 3,05 (Sept., 1H, in), 3.75 (t, J=7,6 Hz, 2H), 4,10 (m, 2H), 4,98 (width, 1H), 6,80 (m, 2H), 7,10 (m, 1H).

Elemental analysis (C17H22N2Cl2OS)

Calculated (%): C 54,69 H 5,94 N 7,50 S 8,59 Cl 18,79

Found (%): C 54,70 H 5,99 N 7,70 S 8,48 Cl 18,82.

Example 146

Synthesis of 2-[1-n-butyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H - imidazol-2-yl]ethanol (Compound 1-146)

In 40 ml of anhydrous dimethylformamide was dissolved 4.0 g (9.5 mmol) of the compound of imidazole (Compound 1-136), and then cooling with ice, was added 670 mg (16,8 mmol) of 60% sodium hydride. After 5 minutes was added 1,95 g (of 14.2 mmol) of n-butylbromide, and the resulting mixture was stirred by heating at 50oC, for 30 minutes. After cooling, the reaction mixture was diluted with ice water and was extracted with ethyl acetate. The extract was washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate), and was obtained 4.1 g of 2-(2-benzyloxyethyl - 1-butyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole (130b) as an oily product (yield 90%).

1H-NMR (CDCl3-TMS) million D.: of 0.82 (t, J= 7.2 Hz, 3H), of 1.23 (d, J= 7,0 Hz, 6H), of 1.30 (m, 2H), 1,50 (solenoi acid was dissolved 4.1 g benzyloxy-connection (130b), and the resulting mixture was stirred by heating at 110oC for 2.5 hours. After cooling, the mixture was neutralized with sodium bicarbonate and was extracted with ethyl acetate. The extract was washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate) and was obtained 3.0 g of the Compound 1-146 in the form of an oily product (yield 90%).

1H-NMR (CDCl3-TMS) million D.: 0,86 (t, J= 7.2 Hz, 3H), 1,21 (d, J= 7,0 Hz, 6H), 1,25 (m, 2H), 1,50 (m, 2H), 2,87 (t, J= 5.8 Hz, 2H), 3,06 (Sept., 1H), 3,79 (t, J= 7.4 Hz, 2H), 4,11 (m, 2H), 5,00 (width, 1H), for 6.81 (m, 2H), 7,10 (m, 1H).

Example 147

Synthesis of 1,2-di-(2-carbamoylethyl)-5-(3,5-dichlorophenylthio)-4 - isopropyl-1H-imidazole (Compound 1-147)

In 59 ml of anhydrous acetonitrile was dissolved 5,00 g (11.9 mmol) of the compound of imidazole (Compound 1-136), after which was added to 3.3 g (of 23.9 mmol) of potassium carbonate and 3.0 g (18 mmol) of ethylbromoacetate, and the resulting mixture was heated at 60oC for 11 hours. After cooling, the reaction mixture was diluted with water, extracted with ethyl acetate, the extract washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The remainder of ocislovanych)-4-isopropyl - 1H-imidazol-1-yl)ethyl acetate (130C) as an oily product (yield 90%).

1H-NMR (CDCl3-TMS) million D.: 1,15 (t, J = 7.2 Hz, 3H), of 1.26 (d, J = 6.8 Hz, 6H), to 3.02 (t, J = 6.2 Hz, 2H), 3,11 (Sept., 1H), 3,83 (t, J = 6.2 Hz, 2H), 4,01 (sq, J = 7.2 Hz, 2H), 4,49 (s, 2H), 4,74 (s, 2H), 6,83 (m, 2H), was 7.08 (m, 1H), 7,29 (m, 5H).

In 30 ml of anhydrous diethyl ether was dissolved 3.0 g (5.9 mmol) of the ester compound (130C), and then when the ice cooling was added 230 mg (6 mmol) of lithium aluminum hydride, and the mixture was stirred for 15 minutes at room temperature. The mixture was diluted with water, extracted with ethyl acetate, the extract washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate), and after recrystallization from a mixture of ethyl acetate and n-hexane was obtained 2.5 g of 2-(2-(2-benzyloxyethyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H - imidazol-1-yl)ethanol (130d) in the form of crystals (yield 91%). So pl. 129-130oC.

1H-NMR (CDCl3-TMS) million D.: a 1.25 (d, J = 7,0 Hz, 6H), 3,11 (m, 4H), 3,63 (m, 2H), 3,92 (t, J = 6.2 Hz, 2H), 4,07 (t, J= 4,8 Hz, 2H), 4,50 (s, 2H), 6,79 (m, 2H), 7,10 (m, 1H), 7,20-7,31 (m, 5H).

Elemental analysis (C23H26Cl2N2O2S)

Calculated (%): C 59,35 H 5,63 Cl 15,23 N 6,02 S 6,89

Found (%): C 59,32 H 5,65 Cl 15,00 N 6,00 S 6,88.

In 15 ml UP>o
C for 7 hours. After cooling, the mixture was neutralized with sodium bicarbonate and was extracted with ethyl acetate, and the extract was washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (3% methanol/ethyl acetate) and got to 1.14 g of 2-(5-(3,5-dichlorophenylthio)-2-(2-hydroxyethyl)-4 - isopropyl-1H-imidazol-1-yl)ethanol (s) as an oily product (yield 94%).

1H-NMR (CDCl3-TMS) million D.: 1,22 (d, J=7.2 Hz, 6H), 2,80 (width, 1H), 2,99 (t, J= 5.4 Hz, 2H), is 3.08 (Sept., 1H), of 3.73 (t, J= 5.0 Hz, 2H), of 4.05 (m, 4H), 4,80 (width, 1H), 6,79 (m, 2H), 7,13 (m, 1H).

In 10 ml of anhydrous tetrahydrofuran was dissolved 1.01 g (2.7 mmol) delovogo connection (s). The solution was cooled to -40oC and dropwise added 1.52 g (8 mmol) trichloroacetimidate. After 5 minutes, the temperature was gradually raised to room temperature, and the mixture is stirred for 1 hour. Then added 2 ml of triethylamine and 4 ml of water, and the mixture was heated at 50oC for 3 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. Were extracted with ethyl acetate. The extract was washed with water, drained svodnyy sodium sulfate, filtered and concentrated in Pont is recristallization from a mixture of ethyl acetate and n-hexane, the result that was obtained 1.0 g (yield 81%) of Compound 1-147 in the form of crystals. So pl. 152-153oC.

1H-NMR (CDCl3-TMS) million D.: of 1.23 (d, J=6.8 Hz, 6H), of 3.07 (Sept., 1H) and 3.15 (t, J= 7.4 Hz, 2H), 4,13 (m, 4H), to 4.52 (t, J= 7.2 Hz, 2H), 4,82 (width, 4H), 6,78 (m, 2H), 7,11 (m, 1H).

Elemental analysis (C18H22Cl2N4O4S)

Calculated (%): C 46,86 H 4,81 Cl Shed 15.37 N 12,14 S 6,95

Found (%): C 46,90 H 4,79 Cl 15,11 N 12,04 S 6,80.

Example 148

Synthesis of 2-(3-carbamoylmethyl)-5-(3,5-dichlorophenylthio)-4 - isopropyl-1-methyl-1H-imidazole (Compound 1-148)

To 300 ml of anhydrous n-hexane was added under ice cooling to 16.4 g (410 mmol) of 60% sodium hydride, and the mixture was stirred. The mixture is then left for some time, and the hexane layer was discarded. To the residue was added 100 ml of anhydrous N,N-dimethylformamide. Further, when the temperature is below 40oC was added dropwise 70 g (410 mmol) of benzylbromide, and the resulting mixture was stirred at the same temperature for 30 minutes, after which the mixture was poured into ice water and was extracted with diethyl ether. The extract was washed with water, dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by fractional distillation under reduced pressure, the result is th amounted to 114oC/0.5 mm RT.article.

1H-NMR (CDCl3-TMS) million D.: 1,71 (m, 4H), and 2.27 (m, 1H), 3,50 at 3.69 (m, 4H), 4.53-in (s, 2H), 7,35 (m, 5H).

Chetyrehosnuju flask with a capacity of 2 liters was downloaded 406 milliliters of anhydrous ethyl acetate and 42.3 g (333 mmol) of oxalicacid, and the resulting mixture was cooled to -70oC, Then at a temperature below - 70oC one drop of solution was added anhydrous dimethyl sulfoxide (53 g, 666 mmol) in anhydrous ethyl acetate (203 ml). After 15 minutes, one drop of solution was added ethanol (133b) (50 g, 278 mmol) in anhydrous ethyl acetate (203 ml) and the resulting mixture is stirred for 45 minutes. Then at -70oC was added 168 ml of triethylamine. The resulting mixture was stirred at the same temperature for half an hour, and then for 1 hour at room temperature. The reaction mixture was diluted with ice water and was extracted with ethyl acetate, and the extract was washed with water, dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was dissolved in 193 ml of acetonitrile and added to 51.6 g (333 mmol) of 2,2-dichloro-3-methylbutyraldehyde. To this mixture under ice cooling was added 336 ml of 28% aqueous ammonia, and the resulting mixture was stirred at 40oC for 7 hours. The reaction mixture was diluted with ice in who has demonstrated under reduced pressure. Received the product 2-(3-benzyloxyphenyl)-4-isopropyl-1H-imidazole (a) were subjected to subsequent iodination reaction without purification.

Chetyrehosnuju flask with a capacity of 1 l was downloaded 25 grams of 40% sodium hydroxide/H2O and 125 ml of water and then added to the solution obtained as described above, imidazole (a) in dioxane (125 ml). Then, with ice cooling was added solid iodine (70,5 g, 278 mmol) and the resulting mixture is stirred. After 1 hour, was added aqueous sodium thiosulfate solution, and then dry ice, after which the mixture was extracted with ethyl acetate. The extract was washed with water, dried with sodium sulfate and concentrated under reduced pressure. The residue was dissolved in diethyl ether and to the solution was added 39 g of oxalic acid. Precipitated crystals were collected by filtration, neutralized with sodium carbonate and was extracted with chloroform. The extract was washed with water, dried with sodium sulfate, filtered and concentrated under reduced pressure, resulting in a received 86,7 g (yield 82%) of 2-(3-benzyloxyphenyl)-5-iodine-4 - isopropyl-1H-imidazole (135b) as an oily product.

1H-NMR (CDCl3-TMS) million D.: a 1.01 (d, J=7,0 Hz, 6H), to 1.98 (quintet, 2H), 2,86 (t, J= 5.4 Hz, 2H), 3,63 (t, J= 5.4 Hz, 2H), 4.53-in (s, 2H), 7,35 (m, 5H), 9,40 (Shir is the train of 48.7 g (137 mmol) of 3,5 - dichlorobenzaldehyde. Then at room temperature was added 2,72 g (342 mmol) of lithium hydride. After that, the temperature was raised to 40oC, and then to 60oC. After 4 hours the mixture was poured into ice water and was extracted with ethyl acetate. The extract was washed with water, dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified with help> column chromatography on silica gel (ethyl acetate) and recrystallized from a mixture of ethyl acetate and n-hexane, resulting in received 70 g (yield 58%) of 2-(3-benzyloxyphenyl)- 5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole (e) in the form of crystals. So pl. 118-119oC.

1H-NMR (CDCl3-TMS) million D.: of 0.95 (d, J= 6.2 Hz, 6H), 2,04 (m, 2H), 2,93 (m, 2H), 3,02 (Sept., 1H), to 3.67 (m, 2H), 4,58 (s, 2H), 6.89 in (m, 2H), 7,02 (m, 1H), 7.38 (m, 5H), 10,06 (width, 1H).

In 25 ml of anhydrous acetonitrile was dissolved 5.0 g (11.5 mmol) of imidazole (e), and then was added 1.7 g (23 ml) of lithium carbonate and 2.2 g (of 17.4 mmol) dimethylsulfate. The resulting reaction mixture was stirred under heating at 70oC for 2 hours. Then the reaction mixture was diluted with water with ice and was extracted with diethyl ether. The extract was washed with water, dried with sodium sulfate, filtered and concentrated under reduced pressure. Stated 60%) of 2-(3-benzyloxyphenyl)-5-(3,5-dichlorophenylthio)-4-isopropyl - 1-methyl-1H-imidazole (a) in the form of massobrio product.

1H-NMR (CDCl3-TMS) million D.: 1,24 (d, J= 6.8 Hz, 6H), 2,07 (m, 2H), 2,88 (t, J= 7,6 Hz, 2H), 3,09 (Sept., 1H), 3,42 (s, 3H), 3,53 (t, J= 6.0 Hz, 2H), 4,50 (s, 2H), 6,77 (m, 2H), 7,10 (m, 1H), 7,32 (m, 5H).

To 3.1 g (6,9 mmol) of the above oily product (a) was added 13 ml of concentrated hydrochloric acid, and the mixture was heated at 110oC for two hours. After cooling, the mixture was neutralized with sodium bicarbonate and was extracted with ethyl acetate. The extract was washed with water, dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: 3% methanol-ethyl acetate) and recrystallized from ethyl acetate/n-hexane, which was obtained 1.6 g (yield 39%) 3-[5-(3,5- dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]-propan-1-ol (a) in the form of crystals, so pl. 124-125oC.

1H-NMR (CDCl3-TMS) million D.: of 1.23 (d, J= 7,0 Hz, 6H), of 2.08 (m, 2H), 2,92 (t, J= 6.0 Hz, 2H), is 3.08 (Sept., 1H), 3.45 points (s, 3H), 3,80 (t, J= 5,2 Hz, 2H), ceiling of 5.60 (Shir.s, 1H), 6,80 (m, 2H), 7,12 (m, 1H).

Elemental analysis (C16H20Cl2N2OS):

Calculated (%): C 53,48 H 5,61 Cl 19,73 N 7,80 S 8,92

Found (%): C 53,30 H 5,59 Cl 19,45 To 7.77 N S 8,77.

In 7 ml of anhydrous tetrahydrofuran was dissolved 700 mg (1.9 mmol) of the above is Anata. After 5 minutes, the temperature was gradually raised to room temperature and the mixture was stirred for 30 minutes. After adding 2 ml of water and 1 ml of triethylamine and the mixture was stirred at room temperature for three days. The reaction mixture was diluted with water and extracted with ethyl acetate, after which the extract was washed with water, dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (3% methanol in ethyl acetate) and recrystallized from ethyl acetate/n-hexane, resulting in received 690 mg (yield 88%) of Compound 1-148 in the form of crystals, so pl. 135-137oC.

1H-NMR (CDCl3-TMS) million D.: of 1.23 (d, J= 7,0 Hz, 6H), 2,11 (m, 2H), 2,84 (t, J= 7.8 Hz, 2H), 3,10 (Sept., 1H), 3,34 (s, 3H), 4,17 (t, J= 6.2 Hz, 2H), 4,71 (Shir.s, 2H), 6,78 (m, 2H), 7,11 (m, 1H).

Elemental analysis (C17H21Cl2N3O2S):

Calculated (%); C 50,75 H 5,26 Cl 17,62 N 10,44 S 7,97

Found (%): C 50,60 H A 5.25 Cl 17,40 N 10,37 S Of 7.85.

Example 149

Synthesis of 2-(3-carbamoylmethyl)-5-(3,5-dichlorophenylthio)-1-ethyl - 4-isopropyl-1H-imidazole (Compound 1-149)

In 25 ml of anhydrous acetonitrile was dissolved 5.0 g (11.5 mmol) of imidazole (e), and then was added 1.7 g (23 mmol) of lithium carbonate and 2.7 g (17.5 mmol) of the Oia, the reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate), resulting in received of 5.3 g (yield 98%) of 2-(3 - benzyloxyphenyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1-ethyl-1H - imidazole (136b) in the form of an oily substance.

1H-NMR (CDCl3-TMS) million D.: 1,15 (t, J= 7.4 Hz, 3H), of 1.23 (d, J=6.6 Hz, 6H), 2,10 (m, 2H), 2,85 (t, J= 7.4 Hz, 2H), 3,07 (Sept., 1H), 3,54 (t, J= 5.4 Hz, 2H), 3,85 (sq, J=7,4 Hz, 2H), 4,50 (s, 2H), 6,78 (m, 2H), was 7.08 (m, 1H), 7,31 (m, 5H).

To 5.3g to (11.4 mmol) of the above oily substance (136b) was added 24 ml of concentrated hydrochloric acid, and the mixture was heated at a temperature of 110oC for 2 hours. After cooling, the mixture was neutralized with sodium bicarbonate and was extracted with ethyl acetate. The extract was washed with water, dried with sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (3% methanol/ethyl acetate) and recrystallized from n-hexane, which was obtained 3.2 g (yield 75%) 3-[5-(3,5- dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl]-propan-1-ol (137b) in the form of crystals, so pl. 73oC.

1H-NMR (CDCl3-TMS) million PC 6.82 (m, 2H), 7,11 (m, 1H).

Elemental analysis (C17H22Cl2N2OS):

Calculated (%): C 54,69 H 5,94 Cl 18,99 N 7,50 S 8,59

Found (%): C 54,54 H 5,88 Cl 18,76 N 7,49 S 8,63.

In 7 ml of anhydrous tetrahydrofuran was dissolved 700 mg (1.9 mmol) of alcohol (137b), and then the solution was cooled to a temperature of -40oC, was added 530 mg (2.8 mmol) trichloroacetimidate, and the temperature was raised to room. After 30 minutes, was added 2 ml of water and 1 ml of triethylamine, and the resulting mixture was stirred at room temperature for three days. The reaction mixture was diluted with water and extracted with ethyl acetate, after which the extract was washed with water, dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (3% methanol/ethyl acetate) and recrystallized from ethyl acetate/n-hexane, resulting in received 705 mg (yield 90%) of Compound 1-149 in the form of crystals, so pl. 128-129oC.

1H-NMR (CDCl3-TMS) million D.: of 1.18 (t, J= 7.2 Hz, 3H), 1,23 (l, J= 6.8 Hz, 6H), of 2.15 (m, 2H), 2,82 (t, J= 7,6 Hz, 2H), is 3.08 (Sept., 1H), a 3.87 (sq, J=7.2 Hz, 2H), 4,18 (t, J= 6.2 Hz, 2H), 4,70 (Shir.s, 2H), to 6.80 (m, 2H), 7,10 (m, 1H).

Elemental analysis (C18H23Cl2N3O2S):

Calculated (%): C 5 is)-5-(3,5-dichlorophenylthio)-4 - isopropyl-1-(pyridine-4-yl)methyl-1H-imidazole (Compound 1-150)

In 50 ml of tetrahydrofuran was dissolved 5.0 g (11.5 mm) imidazole (e), and then added 5 ml of water and 1.84 g (46 mmol) of sodium hydroxide, after which was added 250 mg (0.8 mmol) of bromide n-tetrabutylammonium and 2.3 g (14 mmol) of the hydrochloride of 4-chloromethylpyridine. The resulting mixture was stirred under heating at 50oC for 8 hours. After cooling, the reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (5% methanol in ethyl acetate), resulting in a received 2-(3 - benzyloxyphenyl)-5-(3,5-dichlorophenylthio)- 4-isopropyl-1-(pyridine - 4-yl)methyl-1H-imidazole (s) in the form of an oily substance. To the thus obtained oily substance (s) was added 27 ml of concentrated hydrochloric acid, and the mixture was heated at a temperature of 110oC for 2 hours. After cooling, the mixture was neutralized with sodium bicarbonate and was extracted with ethyl acetate. The extract was washed with water, dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica compound is (output 76%) 3-(5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-4-ylmethyl)- 1H-imidazol-2-yl)-propan-1-ol (s) in the form of crystals, so pl. 106-107oC.

1H-NMR (CDCl3-TMS) million D.: of 1.28 (d, J= 7,0 Hz, 6H), for 2.01 (m, 2H), and 2.83 (t, J= 6.2 Hz, 2H), 3,14 (Sept., 1H), 3,78 (t, J= 5.6 Hz, 2H), 5,10 (s, 2H), 5,34 (Shir.s, 1H), of 6.71 (m, 2H), 6,78 (d, J= 6.0 Hz, 2H),? 7.04 baby mortality (m, 1H), 8,48 (d, J= 6.0 Hz, 2H).

Elemental analysis (C21H23Cl2N3OS):

Calculated (%): C 57,80 H 5,31 Cl 16,25 N 9,63 S 7,35

Found (%): C 57,45 Of 5.40 H Cl 16,02 H 9,50 S 7,28.

In 7 ml of anhydrous tetrahydrofuran was dissolved 700 mg (1.6 mmol) of alcohol (s), and then the solution was cooled to a temperature of -40oC, was added 450 mg (12.4 mmol) trichloroacetimidate, and the temperature was gradually raised to room. After stirring for 30 minutes was added 2 ml of water and 1 ml of triethylamine, and the mixture was stirred at room temperature for three days. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (5% ethanol/ethyl acetate) and recrystallized from ethyl acetate/n-hexane, resulting in received 610 mg (yield 79%) of Compound 1-150 in the form of crystals, so pl. 114-115oC.

1H-NMR (CDCl3-TMS) million D.: of 1.29 (d, J=6,8 Hz,d, J= 5.4 Hz, 2H).

Elemental analysis (C18H23Cl2N3O2S)

Calculated (%): C 51,92 H 5,57 Cl 17,03 of 10.09 N S 7,70

Found (1): C 52,09 H 5,59 Cl 16,69 N 10,01 S 7,53

Example 151

Synthesis of 1-(2-carbamoylethyl)-2-(3-carbamoylmethyl)-5- (3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole (Compound 1-151)

In 50 ml of anhydrous acetonitrile was dissolved 5.0 g (11.5 mmol) of imidazole (e), and then was added 3.2 g (23.2 mmol) of potassium carbonate and 2.9 g (of 17.4 mmol) ethylbromoacetate, and the resulting mixture was heated at a temperature of 60oC for 11 hours. After the reaction mixture was diluted with water with ice and was extracted with ethyl acetate. The extract was washed with water, dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (ethyl acetate:n-hexane = 1:2), resulting in a received 5.75 g (yield 96%) of [2-(3 - benzyloxyphenyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazolyl] ethyl acetate (136d) in the form of an oily substance.

1H-NMR (CDCl3-TMS) million D.: 1,15 (t, J= 7.2 Hz, 3H), 1,24 (d, J= 7,0 Hz, 6H), of 2.08 (m, 2H), 2,80 (t, J= 7.2 Hz, 2H), 3,09 (Sept., 1H), 3,52 (t, J= 5.8 Hz, 2H), 4,03 (sq, J= 7.2 Hz, 2H), 4,48 (s, 2H), 4,60 (s, 2H), PC 6.82 (m, 2H), was 7.08 (m, 1H), 7,31 (m, 5H).

In 30 ml of anhydrous diethyl ether races is imagegrid lithium. The mixture is stirred at room temperature for 15 minutes. Then the reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate) and then recrystallized from n-hexane, resulting in a 2.4 g (yield 87%) 2-[2-(3- benzyloxyphenyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol - 1-yl]-ethanol (e) in the form of crystals. So pl. 104-106oC.

1H-NMR (CDCl3-TMS) million D.: of 1.23 (d, J=7,0 Hz, 6H), 2,12 (quintet, 2H), 2,42 (width, 1H), 2,93 (t, J= 7.2 Hz, 2H), is 3.08 (Sept., 1H), 3,55 (t, J= 6.0 Hz, 2H), to 3.64 (m, 2H), 3.96 points (t, J= 5.8 Hz, 2H), of 4.45 (s, 2H), 6,77 (m, 2H), 7,10 (m, 1H), 7,30 (m, 5H).

Elemental analysis (C24H28Cl2N2O2S)

Calculated (%): C 60,12 of 5.89 H Cl 14,79 of 5.89 N S 6,69

Found (%): C 60,06 H 5,91 Cl 14,54 N 5,78 S 6,64.

To 14 ml of concentrated hydrochloric acid was added 1.4 g (2.9 mmol) of alcohol (e), and the resulting mixture was heated at 110oC for 7 hours. After cooling, the mixture was neutralized with sodium bicarbonate and was extracted with ethyl acetate. The extract was washed with water, dried with sodium sulfate, filtered and kontsentriruyutsya) and received 300 mg (yield 26%) 3-[5-(3,5-dichlorophenylthio)-1-(2-hydroxyethyl)-4 - isopropyl-1H-imidazol-2-yl]-propan-1-ol (137d) as an oily product.

1H-NMR (CDCl3-TMS) million D.: 1,22 (d, J= 6.8 Hz, 6H), to 2.06 (m, 2H), 2,60 (width, 1H), 3,00 (t, J=6.2 Hz, 2H), 3,07 (Sept., 1H), 3,76 (m, 2H), 4,01 (t, J= 5.4 Hz, 2H), 4,60 (width, 1H), 6,80 (m, 2H), 7,13 (m, 1H).

In 5 ml of anhydrous acetonitrile was dissolved 240 mg (0.6 mmol) of diol (137d), after which the solution was cooled to -40oC and was added dropwise to 400 mg (2,11 mmol) trichloroacetyl isocyanate. After 5 minutes, the temperature was gradually raised to room temperature, and the mixture is stirred for 1 hour. Then to the mixture was added 3 ml of water and 1.5 ml of triethylamine, and the resulting mixture was heated at 50oC for 3 hours. The reaction mixture was diluted with water with ice and was extracted with ethyl acetate. The extract was washed with water, dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate) and recrystallized from a mixture of ethyl acetate and n-hexane, resulting in received 127 mg (yield 43%) of Compound 1-151 in the form of crystals. So pl. 155-163oC.

1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J=7,0 Hz, 6H), of 2.16 (m, 2H), 2,86 (m, 2H), 3,07 (Sept. 1H), 4,14 (m, 6H), 4,88 (Shir.s, 4H), 6,78 (m, 2H), 7,11 (m, 1H).

Elemental analysis (C19H24Cl2N4O4S)

Calculated (%): C 48,00 H 5,09 2-carbamoyloximes)-5-(3,5 - dichlorophenylthio)-4-isopropyl-1H-imidazole (Compound 1-152)

In 20 ml of acetone was dissolved 5.0 g of imidazole (101A) and 1.36 g (14.7 mmol) of monochloroacetone, and then added to 2.46 g (12,27 mmol) of potassium iodide, and the mixture was stirred for 30 minutes at room temperature. Then to the mixture was added 2,04 g (of 14.8 mmol) of potassium carbonate, after which the mixture is stirred for 4 hours at 50oC and treated. The reaction mixture is kept under reduced pressure, and the residue was extracted with methylene chloride. The extract was washed with water, dried, and the solvent drove away. The residue was purified by column chromatography on silica gel (methylene chloride:ethyl acetate = 9: 1) and obtained 3.1 g (yield 54%) of 2-benzoyloxymethyl-5-(3,5 - dichlorophenylthio)-4-isopropyl-1-acetylethyl-1H-imidazole (139) in the form of a solid product.

1H-NMR (CDCl3-TMS) million D.: of 1.26 (d, J= 7.2 Hz, 6H), to 3.0-3.2 (m, 1H), of 4.45 (s, 2H), 4,63 (s, 2H), and 4.75 (s, 2H), 6,80 (d, J= 2 Hz, 2H), 7,26-to 7.32 (m, 5H).

In 50 ml of methanol was dissolved 3.6 g of ketone (139), and then cooling with ice and stirring, was added 352 mg (10 mmol) NaBH4and the resulting mixture is stirred for 3 hours at room temperature and processed. The reaction mixture is kept under reduced pressure, the residue was extracted with methylene chloride, washed with water, dried and the solvent drove away. the natural enemy, 2-benzoyloxymethyl-5-(3,5 - dichlorophenylthio)-1-(2-hydroxypropyl)-4-isopropyl-1H-imidazole (140A) as an oily product.

1H-NMR (CDCl3) million D.: 1,40 (d, J= 3,6 Hz, 3H), 1,22-1,3 (m, 6H), to 2.67 (m, 1H), 3,0-3,2 (m, 1H), br4.61 (d, J= 1.4 Hz, 2H), with 4.64, 4,78 (Avcv., J= 12,2 Hz, 29,4 Hz, 2H), 6,28 (d, J= 1.2 Hz, 2H), 7,11 (t, J= 1.6 Hz), 7,33 and 7.36 (5H).

In 55 ml of concentrated hydrochloric acid was dissolved 13,4 g (28.7 mmol) of alcohol (140A), after which the mixture was stirred by heating at 110oC, for 2 hours, and the reaction mixture was added saturated aqueous sodium bicarbonate solution. The mixture is kept under reduced pressure and the residue was extracted with ethylacetate. The extract was washed with water, dried and the solvent drove away. The residue was purified by column chromatography on silica gel (methylene chloride:ethyl acetate = 9:1), and the obtained oily substance was treated with ether and was led, resulting in received of 9.1 g (yield 84%) of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-1-(2-hydroxypropyl)-4 - isopropyl-1H-imidazole (a). So pl. 159-161oC.

1H-NMR (CDCl3) million D.: 1,18-of 1.24 (m, 9H), to 3.0-3.2 (m, 1H), 3,88-4,00 (m, 3H), 4,68, 4,78 (Avcv., J= 13,2 Hz, 21,4 Hz, 2H), 6,79 (d, J= 1.6 Hz, 2H), 7,13 (t, J=2 Hz, 1H).

In 20 ml of tetrahydrofuran was dissolved 1.13 g (3 mmol) of diol (a), then when ohley temperature. After completion of the reaction, to the reaction mixture were added saturated aqueous solution of sodium bicarbonate, the mixture is kept under reduced pressure, and the residue was extracted with methylene chloride. The extract was washed with water, dried and the solvent drove away. The residue was purified by column chromatography on silica gel (methylene chloride:ethyl acetate = 1:2). From the first elyuirovaniya faction received 290 mg (yield 20%) of 2-(N-chloroacetyl)- carbamoyloxymethyl-1-[2-(N-chloroacetyl)carbamoyloximes-5- (3,5-dichlorophenylthio)-4-isopropyl-1H-imidazole (142b) in powder form. From the second elyuirovaniya fractions were obtained 1.08 g (yield 59%) of 2-(N-chloroacetyl)carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-1- (2-hydroxypropyl)-4-isopropyl-1H-imidazole (142a) in the form of an oily product.

1H-NMR (CDCl3) million D.; (142a) of 1.20-1.26 in (m, 9H), 3,0-3,20 (m, 1H), of 3.8-4.1 (m, 3H), of 4.44 (s, 2H), 5,30, 5,47 (Avcv., J= 13,2 Hz, 34.8 Hz, 2H), 6,76 (d, J=2 Hz, 2H), 7,14 (t, J= 3,4 Hz, 1H), 8,43 (width, 1H).

(142b) 1,21-to 1.63 (m, 9H), to 3.0-3.2 (m, 1H), 4,1-to 4.23 (m, 2H), 4,37 is 4.45 (m, 3H), lower than the 5.37 (s, 2H), 6,77 (d, J = 2 Hz, 2H), 7.18 in-7,19 (m, 1H), 8,15-to 8.45 (m, 1H), 8,45-of 8.47 (m, 1H).

In 15 ml of a mixture of water and methanol (1:15) was dissolved 1.08 g (2,18 mmol) of mono(N-chloroacetyl)-connection (142a), then added 50 mg of zinc dust, and the resulting mixture was stirred for 6 hours at room temperaly through celite under reduced pressure, and the filtrate is kept under reduced pressure. The residue was extracted with methylene chloride. The extract was washed with water, dried and the solvent drove away. The residue was purified by column chromatography on silica gel (ethyl acetate) and received 820 mg (yield 90%) of 2 - carbamoyloxymethyl-2-(3,5-dichlorophenylthio)-1-(2-hydroxypropyl)-4 - isopropyl-1H-imidazole (143a) in the form of powder.

1H-NMR (CDCl3) million D.: 1,24-of 1.27 (m, 9H), to 3.0-3.2 (m, 1H), 3.96 points (s, 2H), 3,9-3,98 (m, 1H), 4,86 (width, 2H), 5,2, are 5.36 (Avcv., J= 13 Hz, 32 Hz, 2H), 6,78 (d, J= 2 Hz, 2H), 7,12 (t, 1H).

Elemental analysis (C17H21N3Cl2O3S)

Calculated (%): C 48,81 H 5,16 N 10,04 Cl Of 16.05 S 7,66

Found (%): C 48,75 H 5,27 N 9,90 Cl 16,22 S 7,46.

In 5 ml of a mixture of water and methanol (1:15) was dissolved 290 mg (0.47 mmol) of di(N-chloroacetyl)-connection (142b), and then was added 30 mg of zinc dust, and the resulting mixture was stirred for 6 hours at room temperature. To the reaction mixture were added saturated aqueous solution of sodium bicarbonate, the mixture was filtered through celite under reduced pressure, and the filtrate is kept under reduced pressure. The residue was extracted with methylene chloride. The extract was washed with water, dried and the solvent drove away. The residue was purified by means 152. So pl. 82oC.

1H-NMR (CDCl3) million D.; 1,17-of 1.26 (m, 9H), to 3.0-3.2 (m, 1H), 3,99-4,2 (m, 2H), 4,68-4,93 (width, m, 2H), 5,28 (d, J= 3.8 Hz, 2H), 3,78 (d, J= 1.6 Hz, 2H), 7,13 (t, J= 1.6 Hz, 1H).

Elemental analysis (C18H22N4Cl2O4S0,1H2O)

Calculated (%): C 46,59 H 4,84 N 12,07 S 6,91

Found (%): C 46,98 Of 5.05 H N 11,57 S 6,57.

Example 153

Synthesis of 5-(3,5-dichlorophenylthio)-2-hydroxymethyl-1-(2-hydroxy - 2-methylpropyl)-4-isopropyl-1H-imidazole (Compound 1-153)

In 5 ml of tetrahydrofuran was dissolved 464 mg (1 mmol) of ketone (139), and then was added dropwise, with stirring under ice cooling, 134 mg (1.1 mmol) of bromide Metalmania (tetrahydrofuran, 2 ml) and the resulting mixture is stirred for 30 minutes at room temperature. To the reaction mixture were added an aqueous solution of ammonium chloride, after which the mixture is kept under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with water, dried and the solvent drove away. The residue was purified by column chromatography on silica gel (ethyl acetate:methylene chloride = 1:1), resulting in a received 350 mg (yield 73%) 2-benzoyloxymethyl-5-(3,5 - dichlorophenylthio)-1-(2-hydroxy-2-methylpropyl)-4-isopropyl-1H - imidazole (140b) in the form of an oily product.

1H 2 Hz, 1H).

In 2 ml of concentrated hydrochloric acid was dissolved 350 mg (0.73 mmol) of benzyl compounds (140b), and the resulting solution was stirred for 3 hours under heating at 110oC. To this reaction mixture were added saturated aqueous solution of NaHCO3and the solvent is kept at reduced pressure. The residue was extracted with ethyl acetate, and the extract was washed with water and dried. The solvent is then drove away, and the residue was purified by column chromatography on silica gel (ethyl acetate), resulting in a received 150 mg (yield 53%) of Compound 1-153 in the form of crystals. So pl. 181-182oC.

1H-NMR (CDCl3) million D.: 1,18-of 1.24 (m, 12H), 3.00 and-3,2 (m, 1H) Android 4.04 (s, 2H), and 4.8 (s, 2H), of 6.71 (d, J= 1.6 Hz, 2H), 7,12 (t, J= 1.6 Hz, 1H).

Elemental analysis (C27H22N2Cl2O2S)

Calculated (%): C 52,44 H 5,70 N 7,20 S 8,23 Cl 18,21

Found (%): C 52,30 H 5,74 N 7,19 S 8,30 Cl 18,04.

The following examples illustrate the obtaining pharmaceutical compositions of the present invention. In these examples, the term "active ingredient" means a pharmaceutically acceptable compound of the present invention.

Example 1. Obtaining pharmaceutical compositions

Obtaining tablets

Below Consulate, with the subsequent addition of magnesium stearate and compressing the mixture.

Composition A, mg/tablet:

(a) Active ingredient 200 50

(b) Lactose - 260 5,2

(c) Hydroxypropylcellulose - 15 1,8

(d) Sodium-containing glycolate, starch - 20 2.4GHz

(e) magnesium Stearate - 5 0,6

Only 500 60

Composition B, mg/tablet:

(a) Active ingredient - 200

(b) Lactose - 200

(c) Crystalline cellulose - 60

(d) Hydroxypropylcellulose - 15

(e) Sodium-containing glycolate, starch - 20

(f) magnesium Stearate - 5

Only 500

Composition C, mg/tablet:

(a) Active ingredient - 200

(b) Lactose - 35

(c) Starch - 50

(d) Hydroxypropylcellulose - 12

(e) magnesium Stearate - 3

Only 300

Composition D was obtained by direct sprasowania mixed ingredients.

Composition I, mg/capsule:

(a) Active ingredient - 200

(b) Lactose - 150

(c) Crystalline cellulose - 100

Just - 450

Composition E with controlled release

This composition was prepared by mixing the following ingredients to obtain a solution hydroxypropylcellulose and subsequent wet granulation, adding stearate mA - 400

(b) Hydroxypropylcellulose H - 110

(c) Crystalline cellulose - 60

(d) Hydroxypropylcellulose - 24

(f) magnesium Stearate - 6

Just - 600

Example 2. Obtaining pharmaceutical compositions

Getting capsules

Composition A

These capsules were made by mixing the following ingredients and the subsequent introduction of the mixture in hard gelatin capsule mg/capsule:

(a) Active ingredient - 200

(b) Lactose - 173

(c) Sodium-containing glycolate, starch - 25

(d) magnesium Stearate - 2

Just - 400

Composition B

These capsules were made by melting macrogol 4000, dispersing the active ingredient in the resulting melt, and fill with a mixture of hard gelatin capsules, mg/capsule:

(a) Active ingredient - 200

(b) Macrogol 4000 - 300

Only 500

Composica C

These capsules obtained by dispersing the active ingredient in the lecithin and sesame oil and filling the mixture of hard gelatin capsules, mg/capsule:

(a) Active ingredient - 200

(b) Lecithin - 100

(c) Sesame oil - 100

Just - 400

Composition D (capsules with controlled release)

These capsules with reguliruemym forming pellets of the obtained extrudate and drying of granules. The dried granular product was covered with a film of controlled release and filled this product hard gelatin capsule mg/capsule:

(a) Active ingredient - 200

(b) Microcrystalline cellulose - 125

(c) Lactose - 120

(d) a Wax - 10

Just - 455

Example 3. Obtaining pharmaceutical compositions

Getting syrup

The active ingredient was dissolved in large parts of purified water along with the sodium-containing carboxymethyl cellulose, and then the solution was added sodium benzoate, a solution of D-sorbitol and an aromatic agent. Then added purified water to a final volume of 5 ml, after which the mixture was thoroughly stirred, sieved and homogenized.

(a) Active ingredient - 0.20 g

(b) Sucrose - 0.50 g

(c) D-sorbitol (70% water. solution of 1.00 g

(d) Sodium carboxymethylcellulose - 0.02 g

(e) Polysorbate 80 - 0,005 grams

(f) sodium Benzoate - 0,005 grams

(g) Aromatic additive is 0.01 g

(h) Purified water To 5 ml

Example 4. Obtaining a pharmaceutical composition

Getting suppositories

Fat and oil of the base were dissolved at 45oC. Then, to this fat and oil was added, stirring, active phrases and to room temperature, resulting received suppositories, mg/suppository:

(a) Active ingredient - 200

(b) Fats and oil based - 1800

Just - 2000

Example 5. Obtaining pharmaceutical compositions

Obtaining granules

The following granules were added to hydroxypropylcellulose, the mixture stirred, granulated using a granulator of the type of extruder and drained, resulting in the obtained granules, mg/1 g of granules:

(a) Active ingredient - 200

(b) Corn starch - 325

(b) a Calcium-containing carboxymethylcellulose - 50

(d) Lactose - 350

(e) Hydroxypropylcellulose - 25

(f) CARPLEX - 50

Just - 1000

Example test 1

Analysis of anti-HIV activity of each of the compounds synthesized as described in the above examples, was carried out as follows:

(1) Clone 8 T-cell line human MOLT-4, persistence infected by the virus HIV (strain HTLV-IIIB) were cultured in medium RPM1-1640, to which was added 10% fecal calf serum, and then the culture supernatant was filtered and determined the titer of the virus; the supernatant was stored at -80oC. on the other hand, the test compound was diluted with the above culture medium for predvaritelnogo the Oia. Then added 100 μl-aliquots of the cell suspension MT-4 (3,5104cells per well), and then added 50 μl-aliquots per well (60 b.about.E. (plaque-forming units)) HIV-containing supernatant, diluted the above culture.

(2) Plate and incubated for 5 days in CO2-incubator at 37oC. Then was added 30 μl of 1 per well bromide 3-(4,5 - dimethylthiazol-2-yl)-2,5-diphenyltetrazolium (MTT) (5 mg/ml PBS) and incubation continued for 1 hour. Surviving cells, restoring MTT, cause the deposition of formazan. So from all wells was removed and 150 μl of the supernatant of the culture, and instead, was added 150 μl of a solution containing 10% Triton X-100 and isopropyl alcohol added 0.4% (vol/vol) HCl. The tablet was shaken on a plate shaker for dissolution of formazan; the optical density (OD) of formazan was measured using spectrophotometer for microplates (microliter) at 560 nm and 690 nm (reference wavelength), and the obtained result was compared with the control. The concentration at which this compound inhibited the cytotoxic effect of the virus by 50%, expressed as EC50. The results are presented in tables 1 and 2.

Sample test 2

Was proanalizirovat defined as, as for (2) in the example test 1, except that instead of HIV-containing supernatant (virus suspension) (1) (see example test 1), to each well was added 50 μl of culture medium. The concentration at which the compound was detected 50% cytotoxic effect, meant CC50. The results are presented in tables 3 and 4.

Example test 3

RT-inhibitory (RT-reverse transcriptase) the activity of each of the compounds synthesized as described in the examples were analyzed as follows.

To analyze large numbers of samples used analytical system 96-well plates using purified reverse transcriptase (RT, E. C. 2.7.7.49) recombinant HIV-1 virus, obtained by expression in Escherichia coli. RT-inhibitory activity was determined as follows. To 11 μl solution of the test inhibitor in water or DMSO was added to 100 μl of reaction mixture (0.1 units/100 μl of RT, 50 mm Tris-HCl, pH is 8.3, 150 mm KCl, 10 mm MgCl, 3 mm dithiothreitol, 0.1% of Nonidet P-40, 10 μg/ml poly(rA) and 10 µg/ml (dT) 12-18 as template and primer, and 4 μm dTTP, 1 µci/100 μl of [3H] dTTP as substrate), and the mixture was incubated for 1 hour at 37oC, after which the mixture was immediately cooled the ATEM, using the flush line of the header cells, the cells were washed twice with 5% Na2HPO4/H2O and once with water and dried for 15 minutes at 95oC. then 10 ml of scintillation fluid and filter Mat was placed in a special package, and using a scintillation counter (LKB 1205 Betalate) measured the uptake of [3H] dTMP. Inhibitory activity was expressed as percentage inhibition relative to the radioactivity of the control (water or DMSO).

The concentration at which the compound inhibited reverse transcriptase at 50%, expressed as IC50. The results are presented in tables 5 and 6.

1. Imidazole derivatives of the formula I

< / BR>
or their salts,

where R1represents an alkyl group with 1 to 20 carbon atoms, alkenylphenol group with 2 to 7 carbon atoms, cycloalkylcarbonyl group with 4 to 12 carbon atoms, halogenation group with 1 to 6 carbon atoms, oxoalkyl group with 1 to 6 carbon atoms, aroylamino group with 8 to 13 carbon atoms; aracelio group with 7 to 13 carbon atoms, optionally substituted by alkyl with 1 to 6 carbon atoms, alkenyl, cycloalkyl, halogenation, oxoalkyl, aralkyl, kolkolkol, hydroxy, nitro, NH
R2represents an alkyl group with 1 to 6 carbon atoms, acyl group with 1 to 6 carbon atoms, hydroxylaminopurine group, hydrocodonetylenol group, or a group of the formula -(CH2)n-R4where R4represents halogen, alkoxygroup, the hydroxy-group, cyano, alloctype, aryloxypropanolamine; alkoxycarbonylmethyl; carboxypropyl; karbamoilnuyu group, hydroxyalkyloxy the th-alkyl, alkenyl, cycloalkylation, halogenation, oxoalkyl, acyl, carbamoyl, alkoxy, hydroxyalkyl, aminoalkyl, arylsulfonyl, N-architekturbuero, alkoxycarbonyl, halogenation, alkylsulfonyl or amino, optionally substituted alkyl, acyl, aminoalkyl, carbamoyl or alkylsulfonyl; or sidegroup;

n = 1, 2, 3;

R3represents an alkyl group with 1 to 6 carbon atoms, optionally substituted by hydroxy, alkoxy, acyloxy, alkenyl, cycloalkyl, halogen, oxoalkyl, aralkyl, arilalkilamin, cyano, carboxy or alkoxycarbonyl;

X and Y independently represent hydrogen, alkyl group with 1 to 3 carbon atoms, halogen or nitro-group;

Z IS S, SO, SO2or CH2.

2. Connection on p. 1, where the specified imidazole derivative is a compound of formula I'

< / BR>
where R1, R2, R3X, Y, and Z are defined above.

3. Connection on p. 1, where R1represents an alkyl group with 1 to 6 carbon atoms, hydroxyalkyl group with 1 to 6 carbon atoms or pyridylmethyl group.

4. Connection on p. 1, where R2represents a group of formula -(CH2)n-R4in which R4the submitted the

6. Connection on p. 1, where X and Y independently is halogen.

7. Connection on p. 1, where Z is s

8. Connection on p. 1, where the specified derivative of imidazole are:

(A-1) 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazole;

(And-2) 2-[5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]ethanol;

(A-3) 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-4-isopropyl-1-(pyridine-4-yl)methyl-1H-imidazole;

(A-4) [5-(3,5-dichlorophenylthio)-1-ethyl-4-isopropyl-1H-imidazol-2-yl]methanol;

(A-5) [1-(2-hydroxypropyl)-5-(3,5-dichlorophenylthio-4-isopropyl-1H-imidazol-2-yl]methanol;

(And-6) [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl] acetonitrile;

(A-7) [5-(3,5-dichlorophenylthio)-1-(4-aminobenzyl)-4-isopropyl-1H-imidazol-2-yl]methanol;

(A-8) [5-(3,5-dichlorophenylthio)-1-(3-aminobenzyl)-4-isopropyl-1H-imidazol-2-yl]methanol;

(And-9) 2-[5-(3,5-dichlorophenylthio)-4-isopropyl-1-ethyl-1H-imidazol-2-yl] ethanol;

(A-10) 2-[2-(carbamoylated)ethyl] -5-(3,5-dichlorophenylthio-1-ethyl-4-isopropyl-1H-imidazole;

(A-11) [5-(3,5-dichlorophenylthio)-4-isopropyl-1-(6-oxo-1,6-dihydropyridines-3-yl)methyl-1H-imidazol-2-yl]methanol;

(A-12) 2-carbamoyloxymethyl-5-(3,5-dichlorophenylthio)-1-(6-oxo-1,6-dihydropyridines-3-yl)methyl-4-isopropyl-1H-imidazole;

(A-13) 2-Benzi-isopropyl-1-(pyridine-4-yl)methyl-1H-imidazol-2-yl]methanol.

9. The pharmaceutical composition against HIV-containing compound under item 1 as an active ingredient.

Priority points and features:

26.09.94 on PP.1 and 2; R1is methyl, ethyl, propyl, benzyl, allyl, vermeil, trifluoromethyl; R2group - (CH2)n-R4where n = 1; R4- carbamoylated or thiocarbamoylation possibly replaced by stands; Z Is S; R3is isopropyl; X and Y are hydrogen, halogen or nitro-group;

15.03.95 on PP.1 and 2; R1is an alkyl group with 1 to 20 carbon atoms, Alchemilla group with 2 to 7 carbon atoms, cycloalkenyl group with 4 to 12 carbon atoms, kalkilya group with 7 to 13 carbon atoms, heteroallyl group, including as heteroaryl 5-10-membered cycle; R2is alkyl with 1 to 6 carbon atoms or the group -(CH2)n-R4where n=1, R4-carbamoylated or thiocarbamoylation, substituted alkyl; R3is an alkyl group with 1 to 4 carbon atoms, possibly substituted by hydroxy, halogen, cyano, alkoxycarbonyl; Z-SO, SO2or CH2; X and Y are the lower alkyl group with 1 to 3 carbon atoms;

12.08.95 on PP.1 and 2; R1- halogenation group with 1 to 6 carbon atoms, oxoalkyl group with 1 to 6 ilen group with 7 13 carbon atoms, substituted as specified in those paragraphs, heteroallyl group, including as heteroaryl 5-10-membered cycle, optionally benzoannelirovannykh, having as a heteroatom, 1 sulfur atom or nitrogen; unsubstituted or substituted as specified in those paragraphs, carbamylcholine, carbamylcholine or aryloxyalkyl group, or branched hydroxyalkyl group; R2- acyl group with 1 to 6 carbon atoms; hydroxylaminopurine group, gidrotonnelya group, or a group -(CH2)n-R4where n = 1 to 3, R4-halogen, alkoxy, hydroxy, cyano, acyloxy, aryloxypropanolamine, alkoxycarbonyl; unsubstituted or substituted as specified in those paragraphs, carboxy-, carbarnoyl, hydroxyalkyloxy-, amino-, benzyloxy-, carbamoylated or thiocarbamoyl group; R3is unsubstituted or substituted as specified in those paragraphs, an alkyl group with 1 to 6 carbon atoms; PP.3 - 8 and 9.

 

Same patents:

The invention relates to new thienyl or shilparamam compounds of General formula I, where each R, R1and R2independently represents hydrogen, halogen, NO2or SNO or R1and R2taken together with the carbon atoms to which they are linked, may form a ring in which R1, R2represented by structure II, in which each L, T, V and W is hydrogen, halogen, represents O or S, X represents CN, NO2provided that substituent in the 2 - or 5-position of the pyrrole ring is other than hydrogen, Y is halogen, C1-C6-halogenated, CN, phenyl, optionally substituted by one or more halogen atoms, Z represents a halogen or C1-C6-halogenoalkane, is an R6where R6is hydrogen or C1-C6-alkyl, substituted by one C1-C4-alkoxygroup

The invention relates to the field of organic chemistry and pharmaceuticals, namely heterobicyclic compounds and pharmaceutical compositions based on them, as well as methods of producing these compounds

The invention relates to chemistry, namely the synthesis of biologically active compounds

The invention relates to new 4-substituted piperidine derivative that is related to ones antagonists neirokinina 2 (NK), which can be used, for example, in the treatment of diseases such as asthma, and method of production thereof

The invention relates to 2-[(dihydro)pyrazolyl-3'-oxymethylene] anilides formula I

< / BR>
in whichmeans simple or double bond, and the index and the substituents have the following meanings:

n means 0, 1 or 2;

m means 0, 1 or 2 and the substituents R2may be different if m is greater than 1;

X represents a direct bond, O or NRa;

Rameans hydrogen;

R1means halogen or C1-C4alkyl, or, if n is 2, represents optionally associated with two adjacent ring atoms of the hydrocarbon bridge containing 3 or 4 carbon atoms;

R2means nitro, halogen, C1-C4alkyl, C1-C4halogenated or1-C4alkoxycarbonyl;

R3means optionally substituted alkyl, optionally substituted saturated cycle or optionally substituted single or dual core aromatic radical, which together with the carbon atoms may contain as members of the cycle from one to four nitrogen atoms;

R4means hydrogen, optionally substituted alkyl;

The invention relates to new chemical compounds with valuable biological properties, in particular to derive hinolan and naphthyridinone acids with antibacterial activity, as well as to the isoindole derivative as starting compounds for obtaining the derivatives hinolan and naphthyridinone acid

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The invention relates to a method for producing intermediates for the synthesis of substituted imidazole derivatives of formula I, where R1is phenyl, naphthyl, substituted COOR3; R2- C2-C8-alkyl; R3- N or C1-C6-alkyl; n = 1, the interaction of compound II with compound III, where X is chlorine, bromine, fluorine or iodine, Y OR4, R4- C1-C6-alkyl, in the environment of a solvent in the presence of a base

The invention relates to the field of organic chemistry, in particular to methods of synthesis of heterocyclic compounds and can be used in the production of imidazole needed to obtain drugs and sorbents

The invention relates to oxime derivative of formula I, where R1- H, C1-6-alkyl, R2- C2-6-alkylene, X - C6-10-aryl unsubstituted or substituted by 1 Deputy selected from the group comprising C1-6-alkyl, HE, alloctype, C1-4-alkoxygroup, halogen atoms, phenyl, phenylthiourea, phenylsulfonyl group, phenylcarbonylamino, pyridylsulfonyl group, imidazolidine and peredelnye group or heteroaromatic group: pyridyl, chinosol and imidazolyl ; Y = O, S, orZ represents a group of the formula (For), (Zв ), (Zс ) or ( Zd )
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