Azasteroid connection

 

(57) Abstract:

Usage: as compounds useful for the treatment and prevention of prostatic hypertrophy. Entity: product: azasteroid compounds of General formula I

< / BR>
where R1- H, substituted C1-C4-alkyl, benzyl; R2- C1-C4substituted phenyl, shriley or thienyl group; R3- H, substituted C1-C4-alkyl, alkyl (C1-C4substituted hydroxyl or carboxyl group, or R3alkenyl C3-C6, -A-B - C-D - a - carbon - carbon single or double connection, and these phenyl groups may be substituted by at least one Deputy, such as C1-C6-alkoxy, C2-C4-alkoxycarbonyl, hydroxy, halogen, acetaminophe. Compound I is able to inhibit 5-reductase. table 4.

The invention relates to certain new azasteroid compounds useful for the treatment and prevention of hypertrophy prostate, and provides methods and compositions, their use and methods for their preparation.

Treatment of hypertrophy of the prostate is extremely limited, although it has been shown that compounds that inhibited the tats, and U.S. patent N 4179453 and N 4760071 open multiple connections with this type of activity, and thus may be useful for this purpose. Of these compounds the most active and, apparently, most similar to the compounds according to the invention are the compounds of formula (A)

< / BR>
in which R' and R" both represent ethyl group (compound A1or R' represents a hydrogen atom and R" represents a tert-boutelou group (compound A2).

However, while these compounds do not have sufficient activity, so there is a need to develop compounds with higher activity.

It is now established that connection with some specific carbamoyl substituents in the 17th position azasteroid skeleton, have high inhibitory activity against 5-alpha-reductase, and therefore can be used for treatment and prophylaxis of the aforementioned diseases.

The aim of the invention is the development of a number of new azasteroid compounds that may be useful for the treatment and prevention of prostatic hypertrophy.

Further and more specific objective of izaberete and prevention of hypertrophy of the prostate.

Compounds according to the invention are azasteroid compounds that have the formula I:

< / BR>
in which R1represents a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, or a substituted alkyl group having 1 to 6 carbon atoms which is substituted by at least one Deputy, selected from the group comprising aryl group, as defined below, an aromatic heterocyclic group, as defined below, carboxypropyl and actigraphy;

R2represents a substituted alkyl group having 1 to 6 carbon atoms which is substituted by at least one Deputy, selected from the group comprising aryl group, as defined below, and aromatic heterocyclic groups as defined below, and which is not substituted or otherwise substituted by at least one additional Deputy selected from the group including carboxypropyl or actigraphy, or diarylamino;

R3represents a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted alkyl group having 1 to 6 carbon atoms which is substituted by at least one Deputy, selected the th group, having 3 to 6 carbon atoms: each of the connections represented as alpha -, beta-and gamma-Delta is a carbon-carbon simple bond (-CH2-CH2- or carbon-carbon double bond (-CH=CH-),

mentioned aryl groups are aryl carboxylic groups which have 6 to 10 carbon ring atoms and which is not substituted or is substituted by at least one Deputy, selected from the group comprising alkyl groups having 1 to 6 carbon atoms, alkoxygroup having 1 to 6 carbon atoms, alkoxycarbonyl group having 2 to 7 carbon atoms, actigraphy, halogen atoms and groups of formula-otherawhere Rarepresents an aliphatic carboxylic acyl group having 1 to 5 carbon atoms, mentioned aromatic heterocyclic groups are 5 or 6 ring atoms, of which from 1 to 3 heteroatoms selected from the group comprising heteroatoms of nitrogen, oxygen and sulfur, and is not substituted or is substituted by at least one Deputy, selected from the group comprising alkyl groups having 1 to 6 carbon atoms, alkoxygroup having 1 to 6 carbon atoms, and halogen atoms;

and pharmaceutically acceptable salts and esters of the compounds.

The invention further provides another method of treating hypertrophy of the prostate, which includes the introduction of an animal, preferably a mammal, which may be people, at least one active connection, representing at least one compound of formula I or its pharmaceutically acceptable salt or ester.

The invention also provides methods of making compounds according to the invention, described in more detail below.

In the compounds of the formula I, in which R1represents an alkyl group having 1 to 6 carbon atoms, the alkyl group may be straight or branched chain comprising from 1 to 6 carbon atoms, and examples include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, hexyl and isohexyl. Of these groups, preferred alkyl groups having 1 to 4 carbon atoms, preferably methyl, ethyl, sawn, ISO-propyl, boutelou and isobutylene group, more preferably methylin is or it may be substituted by at least one Deputy, preferably one or two substituents selected from the group comprising aryl group, as defined above and shown in the examples below, an aromatic heterocyclic group as defined above and shown in the examples below, a carboxyl group and actigraphy.

Examples of such aryl groups include phenyl and raftiline (1 - or 2-naphthyl) group, which can be not substituted or is substituted by one or more of the following groups, preferably from 1 to 3 groups, and more preferably one or two groups selected among:

alkyl groups having 1 to 5 carbon atoms, for example methyl, ethyl, ISO-propyl, bucilina, isobutylene, second-bucilina, tert-bucilina, pentilla, isopentyl, neopentyl, exilda and isohexyl groups, of which the preferred methyl and ethyl group, and most preferred methyl group,

alkoxygroup having 1 to 6 carbon atoms, for example methoxy-, ethoxy-, propoxy-, isopropoxy, butoxy, isobutoxy-, second -, butoxy-, tert-butoxy, pentyloxy, isopentylamine, neopentylene, hexyloxy and isohexadecane, of which preferred methoxy - and ethoxypropan and the most preferred metal is ohms fluorine and chlorine,

alkoxycarbonyl groups having 2 to 7, preferably 2 to 5, carbon atoms (i.e., itself CNS part contains 1 to 6, preferably 1 to 4, carbon atoms), such as methoxycarbonyl, etoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, butoxycarbonyl, isobutoxide, second-butoxycarbonyl, tert-butoxycarbonyl, pentyloxybenzoyl, isopentylamine, neopentylglycol, hexyloxybenzoyl and isohexadecane, of which preferred methoxycarbonyl and ethoxycarbonyl group;

groups of the formula-otherawhere Rarepresents an aliphatic carboxylic acyl group having 1 to 5 carbon atoms, for example formyl, acetyl, propionyl, butyryloxy, valerino, isovaleryl and pivaloyl groups, of which the preferred formal and acetyl group;

exigrep.

Examples of substituted and unsubstituted aryl groups include phenyl, 1-naftalina, 2-naftalina, 2-, 3 - and 4-trillou, 2-, 3 - and 4-metoksifenilny, 2-, 3 - and 4-ethylphenyl, 2-, 3 - and 4-ethoxyphenyl, 2-, 3 - and 4-chloraniline, 2-, 3-, 4-florfenicol, 2-, 3 - and 4-oxyphenylic, 2-, 3 - and 4-acetamidophenyl and 2, 3 - and 4-formimidoyl group.

Where sameshima are heteroatoms, selected from the group comprising heteroatoms of nitrogen, oxygen and sulfur. Heterocyclic group may be unsubstituted or may be substituted by at least one Deputy, selected from the group comprising alkyl groups having 1 to 6 carbon atoms, alkoxygroup having 1 to 6 carbon atoms, and halogen atoms from the number shown in the examples above. Where there are three heteroatoms, preferably, at least one (preferably two) were nitrogen atom and one or two should be nitrogen atoms, oxygen or sulfur (in the case of two they may be the same or different). If there are two heteroatom, they may be the same or different and selected from among the atoms of nitrogen, oxygen and sulfur, but preferably, if one is a nitrogen atom or an oxygen atom, the other is a nitrogen atom, oxygen or sulfur. Such groups can be unsubstituted or can be substituted by at least one (preferably 1 to 3) Deputy from among defined above. Examples of such unsubstituted groups include follow (2 or 3), thienyl (2 - or 3-), pyridinol (2-, 3 - or 4-), pyrrolidinyl (2 - or 3-), imidazole (2-, 4 - or 5-), thiazolidine (2-, 4 - or 5-), isonline (2-, 4-, 5 -, or 6-) and pyridinoline (3-, 4-, 5 -, or 6-) groups, of which the preferred furilla and thienyl groups, and in particular thienyl group.

If R2represents a substituted alkyl group, the alkyl part may be any of the alkyl groups described for the example above in connection with R1and the group is necessarily substituted by at least one, preferably from 1 to 5 (depending on the availability of capable of substitution positions), more preferably from 1 to 3 and most preferably one or two substituents, and they must include at least one Deputy, selected from the group comprising aryl group and aromatic heterocyclic group, both of which may be those described for the example above in relation to substituents on the groups represented by the radical R1and can optionally contain, in addition carboxy or axisymmetrical.

If R2is diarylamino, the two aryl part may be the same or different and they can be as described for the example above in connection with aryl substituents at R1. Preferably such groups are diphenylamino.

1. Alternative R3can be alkenylphenol group. If R3represents alkenylphenol group, it has 3 to 6 carbon atoms and may be a group with a straight or branched chain. Examples of such groups include allyl, metallinou, 2-butenyloxy, 2-pentanediol Il 2-hexenyl groups, of which the preferred group having 3 or 4 carbon atoms, especially allyl group.

Preferably the link represented alpha-beta, is a carbon-carbon simple relationship, and the relationship represented by gamma-Delta is a carbon-carbon simple bond or a carbon-carbon double bond, or a bond represented by alpha-beta, is a carbon-carbon double bond and the bond represented by gamma-Delta is a carbon-carbon simple communication.

Examples of preferred groups can be represented by formula)-amino, (2-, 3 - or 4-terbisil)-amino, (2-, 3 - or 4-chlorbenzyl)-amino, phenethylamine, (2-, 3 - or 4-methylpentyl)-amino, (2-, 3 - or 4-methoxyphenethyl)-amino, (2-, 3 - or 4-florfenicol)-amino, (2-, 3 - or 4-chlorphenyl)-amino, (3-phenylpropyl)-amino, (1-methyl-1-phenylethyl)-amino, /1-methyl-1-(2-, 3 - or 4-were)-ethyl/-amino, /1-methyl-1-(2-, 3 - or 4-methoxyphenyl)-ethyl/-amino, /1-methyl-1-(2-, 3 - or 4-chlorophenyl)-ethyl/-amino, /1-methyl-1-(2-, 3 - and 4-chlorophenyl)-ethyl/-amino, /1-methyl-1-2-(2-, 3- and 4-chlorophenyl)-ethyl/-amino, /1-1-methyl-2-, 3 - or 4 oksifenil)-ethyl/-amino, /1-methyl-1-(2-, 2 - or 4-acetamidophenyl)-ethyl/-amino, /1-methyl-1-(2,3-, 2,4-, 2,5-, 2,6-, 3,4-, 3,5- or 3,6-acid)-acylamino, (1,1-dimethyl-2-phenylethyl)-amino, (1,1-dimethyl-2-(2-, 3 - or 4-were)-ethyl/-amino, (1,1-dimethyl-2-(2-, 3 - or 4-methoxyphenyl)-ethyl/-amino, /1,1-dimethyl-2-(2-, 3 - or 4-chlorophenyl)-ethyl/-amino, /1,1-dimethyl-2-(2-, 3 - or 4-forfinal)-ethyl/-amino, benzhydrylamine, /(2-, 3 - or 4-), (2'-, 3'- or 4-)-diferensial/-amino, /(2-, 3 - or 4-), (2'- 3'- or 4-)-dimethoxybenzamide/-amino, (2-, 3 - or 4-chlorobenzhydryl)-amino, (2-, 3 - or 4-methoxybenzyl)-amino, (2-, 3 - or 4-oxybenzyl)-amino, /(2-, 3 - or 4-), (2'-, 3'- or 4-)-dimethylbenzamide/-amino, (1,1-diphenylether)-amino, (1,2-diphenylether)-amino, /2-(2-, 3- or 4-chlorophenyl)-1-phenylethyl/-amino, /1-(2-, 3- or 4-chlorophenyl)-2-(2-, 3- or 4-chlorophenyl)-ethyl/the Nile)-1-phenylethyl/-amino, /1-(2-, 3 - or 4-chlorophenyl)-2-(2-, 3- or 4-forfinal)-ethyl/-amino, /1-(2-, 3- or 4-chlorophenyl)-2-(2-, 3-or 4-methoxyphenyl)-ethylamino, /1-(2-, 3- or 4-chlorophenyl)-2-(2-, 3- or 4-were)-ethyl/-amino, /1-(2-, 3- or 4 oksifenil)-2-(2-, 3- or 4 oksifenil)-ethyl/-amino, /2-(2-, 3- or 4-forfinal)-1-(2-, 3- or 4-were)-ethyl/-amino, /2-(2-, 3- or 4-forfinal)-1-(2-, 3- or 4-methoxyphenyl)-ethyl/-amino, /2-(2-, 3- or 4 oksifenil)-1-phenyl)-ethyl/-amino, /1-(2-, 3- or 4-methoxyphenyl)-2-phenylethyl)-amino, /1-methyl-1,2-diphenyl)-amino, (2,2-diphenylether)-amino, /2-(2-, 3- or 4-methoxyphenyl)-2-(2-, 3- or 4-methoxyphenyl)-ethyl/-amino, /2-(2-, 3- or 4 were)-2-(2-, 3- or 4-were)-ethyl/-amino, (1-benzyl-4-phenylbutyl)-4-amino, (1,1-diphenylether/-amino, /1-(2-, 3- or 4-chlorophenyl)-1-(2-, 3- or 4-forfinal)-ethyl/-amino, /1-(2-, 3- or 4 were)-1-(2-, 3-, or 4-were)-ethyl/-amino, /1-(2-, 3- or 4-methoxyphenyl)-1-(2-, 3- or 4-methoxy-phenyl)-ethyl/-amino, /1-(2-, 3- or 4 oksifenil)-1-phenylethyl/-amino, triphenylethylene, /2-(2-, 3- or 4-), (2'-, 3'- or 4'-), (2"-, 3"-, 4"-)-triftoratsetilatsetonom, /2-(2-, 3- or 4-), (2'-, 3'- or 4'-), (2"-, 3"-, 4"-)-trimethylsilylmethylamine, /1-(2-, 3) or 4-terbisil)-2-(2-, 3- or 4-tryptophanyl)-ethyl/-amino, (1-benzyl-1-methyl-2-phenylethyl)-amino, /1-(2-, 3- or 4-Chlorobenzyl)-2-(2-, 3- or 4-chlorophenyl)-ethyl/-amino, /1-(2-, 3- or 4-terbisil)-2-(2-, 3- or 4-forfinal)-Lee 4-chlorophenyl)-1-methylpropylamine, (1,3-diphenylpropyl)-amino, /1-(2-, 3- or 4-Chlorobenzyl)-3-(2-, 3- or 4-were)-propyl/-amino, /1-(2-, 3- or 4-methoxyphenyl)-3-(2-, 3- or 4-methoxyphenyl)-propyl/-amino, (1,4-diphenylmethyl)-amino, /1-(2-, 3- or 4-chlorbenzyl)-4-(2-, 3- or 4-chlorophenyl)-butyl/-amino, /1-(2-, 3- or 4-methoxyphenyl)-4-(2-, 3- or 4-chlorophenyl)-butyl/-amino, (1-methyl-3,3-diphenylpropyl)-amino, /3-(2-, 3- or 4-terbisil)-3-(2-, 3- or 4-forfinal)-1-methylpropyl/-amino, /1-methyl-3-(2-, 3 - or 4-were)-3-(2-, 3- or 4-were)-propyl/-amino, N-benzyl-N-methylamino, N-benzyl-N-ethylamino, N-benzyl-N-isopropylamino, N-benzyl-N-isobutylamino, N-benzyl-N-tert-butylamino, N-(2, 3 - or 4-terbisil)-N-isopropylamino, N-(2, 3 - or 4-chlorbenzyl)-N-isopropylamino, N-(2, 3 - or 4-methylbenzyl)-N-isopropylamino, N-(2, 3 - or 4-methoxybenzyl)-N-isopropylamino, N-(2, 3 - or 4-oxybenzyl)-N-isopropylamino, N, N-dibenzylamine, N-benzyl-(2-, 3 - or 4-methoxybenzyl)-amino, N-(2, 3 - or 4-terbisil)-N-(2-, 3 - or 4-terbisil)-amino, N-(2, 3 - or 4-methylbenzyl)-N-(2-, 3 - or 4-methylbenzyl)-amino, N-(2, 3 - or 4-methoxybenzyl)-N-(2-, 3 - or 4-methoxybenzyl)-amino, N-(2, 3 - or 4-oxybenzyl)-N-(2-, 3 - or 4-oxybenzyl)-amino, N-benzyl-N-phenethylamine, N-benzyl-N-(1-phenylethyl)-amino, N-benzyl-N-(1-methyl-phenylethyl)-amino, N,N-definitionin, N, N-bis(1-phenylethyl)-amino, N-benzyl-N-(3-phenylpropyl)-amino, (2 and 3-thienylmethyl)-amino, /2-(2 - or 3-furyl-2-ethyl/-amino, /2-(2 - or 3-furyl-2-ethyl/-amino, /3-(2 - or 3-furyl-2-propyl/-amino, /3-(2 - or 3-thienyl)-propyl/-amino, (bis-(2 - or 3-furyl)-methyl/-amino, /bis-(2-or 3-thienyl)-methyl/-amino, /1,1-bis-(2 - or 3-furyl)-ethyl/-amino, /1,1-bis-(2 - or 3-thienyl)-ethyl/-amino, /(2 - or 3-methyl-2-or 3-furyl), 2 - or 3-methyl-2 - or 3-methyl-2 or 3-furyl)-methyl/-amino, /(2 - or 3-methyl-2-or 3-thienyl), 2 - or 3-methyl-2 - or 3-thienyl-methyl/-amino, /1-(2-or 3-furyl)-1-methylethyl/-amino, /1-(2-or 3-thienyl)-1-methylethyl/-amino, /1-(2-or 5-methyl)-2 - or 3-thienyl)-1-methylethyl/-amino, /1-(2-or 5-methyl)-2 - or 3-furyl)-1-methylethyl/-amino, /1-(2-or 3-furyl)-2-(2 - or 3-furyl)-1-ethyl/-amino, /1-(2-or 3-furyl)-2-(2 - or 3-thienyl)-ethyl/-amino, /1-(2-or 3-furyl)-2-phenylethyl/-amino, /1-(2-or 3-furyl)-2-, 3-or 4-were)-ethyl/-amino, /2-phenyl-1-(2 - or 3-thienyl)-ethyl/-amino, /1-phenyl-2-(2-(2 - or 3-thienyl)-ethyl/-amino, /2-(2-, 3- or 4-were)-1-(2 - or 3-thienyl)-ethyl/-amino, /2-(2-, 3- or 4-chlorophenyl)-1-(2 - or 3-thienyl)-ethyl/-amino, /2-(2-, 3- or 4-forfinal)-1-(2 - or 3-thienyl)-ethyl/-amino, /1-(2-, 3- or 4-methoxyphenyl)-1-(2 - or 3-thienyl)-ethyl/-amino, N-(2 - or 3-furylmethyl)-N-(2 - or 3-furylmethyl)-amino, N-(2 - or 3-thienylmethyl)-N-(2 - or 3-thienylmethyl)-amino, /1-(2-, 3- or 4-forfinal)-2-(2 - or 3-thienyl)-ethyl/-amino, N-benzyl-N-(2 - or 3-furylmethyl)-amino, N-benzyl-N-(2 - or 3-thienylmethyl toxigenic)-N-phenylhydrazine, N-(2-, 3 - or 4-chlorophenyl)-N-phenylhydrazine, N-(2-, 3 - or 4-forfinal)-N-phenylhydrazine, N-(2-, 3 - or 4 oksifenil)-N-phenylhydrazine, N-(2-, 3 - or 4-acetamidophenyl)-N-phenylhydrazine, N-(2-, 3 - or 4-were)-N-(2-, 3 - or 4-were)-hydrazine and N-(2-, 3 - or 4-methoxyphenyl)-N-(2-, 3 - or 4-methoxyphenyl)-hydrazine.

More preferred of these groups include the following groups: (1-methyl-1-phenylethyl)-amino, /1-methyl-1-(2-, 3 - or 4-were)-ethyl/-amino, /1-methyl-1-(2-, 3 - or 4-methoxyphenyl)-ethyl/-amino, (1-methyl-1-(2-, 3 - or 4-chlorophenyl)-ethyl/-amino, (1-methyl-1-(2-, 3 - or 4-forfinal)-ethyl/-amino, (1-methyl-1-(2-, 3 - or 4 oksifenil)-ethyl/-amino, (1-methyl-1-(2-, 3 - or 4-acetamidophenyl)-ethyl/-amino, /1-methyl-1-(2,3- 2,4-, 2,5-, 2,6-, 3,4- 3,5- or 3,6 - acid)-ethyl/amino, (1,1-dimethyl-2-phenylethyl)-amino, benzhydrylamine, /(2-, 3 - or 4-), (2'-, 3'- or 4'-)-diferensial/-amino, (2-, 3 - or 4-), (2'-, 3'- or 4'-)-dimethoxybenzyl)-amino, (2-, 3 - or 4-chlorobenzhydryl)-amino, (2-, 3 - or 4-methoxybenzyl)-amino, (2-, 3 - or 4-farbenspiel)-amino, (2-, 3 - or 4-methylbenzhydryl)-amino, (2-, 3 - or 4-oxybenzyl)-amino, (2-, 2 - or 4-), (2'-, 3'- or 4'-)-dioxybenzene/-amino, (2-, 2 - or 4-), (2'-, 3'- or 4'-)-dimethylbenzamide/-amino, (1.1-diphenylether)-amino, (1,2-diphenylether)-amino, /2-(2-, 3- or 4-chlorophenyl)-1-phenylethyl/-amino, /2-(2-, 3- l)-1-phenylethyl/-amino, /2-(2-, 3 - or 4-methoxyphenyl)-1-phenylethyl/-amino, /2-(2-, 3- or 4-chlorophenyl)-2-(2-, 3- or 4-forfinal)-ethyl/-amino, /2-(2-, 3- or 4 were)-2-(2-, 3- or 4-were)-ethyl/-amino, /2-(2-, 3- or 4 oksifenil)-2-(2-, 3- or 4 oksifenil)-ethyl/-amino, /2-(2-, 3- or 4-forfinal)-2-(2-, 3- or 4-were)-ethyl/-amino, /2-(2-, 3- or 4-forfinal)-2-(2-, 3- or 4-methoxyphenyl)-ethyl/-amino, /2-(2-, 3- or 4 oksifenil)-2-(2-, 3- or 4-phenylethyl/-amino, /2-(2-, 3- or 4-methoxyphenyl)-2-(2-, 3- or 2-phenylethyl/-amino, (1-methyl-1,2-diphenylether)-amino, (2,2-diphenylether)-amino, (1,1-diphenylether)-amino, /1-(2-, 3- or 4-forfinal)-1-(2-, 3- or 4-forfinal)-ethyl/-amino, /1-(2-, 3- or 4 were)-1-(2-, 3- or 4-were)-ethyl/-amino, /1-(2-, 3- or 4-methoxyphenyl)-1-(2-, 3- or 4-methoxyphenyl)-ethyl/-amino, /1-(2-, 3- or 4 oksifenil)-1-(2-, 3- or 1-phenylethyl/-amino, triphenylethylene, (1-benzyl-2-phenylethyl)-amino, (1-benzyl-1-methyl-2-phenylethyl)-amino, N-benzyl-N-methylamino, N-benzyl-N-ethylamino, N-benzyl-N-isopropylamino, N-benzyl-N-isobutylamino, N-benzyl-N-tert-butylamino, N-(2-, 3 - or 4-terbisil)-N-isopropylamino, N-(2-, 3 - or 4-chlorbenzyl)-N-isopropylamino, N-(2-, 3 - or 4-methylbenzyl)-N-isopropylamino, N-(2-, 3 - or 4-methoxybenzyl)-N-isopropylamino, N-(2-, 3 - or 4-oxybenzyl)-N-isopropylamino, N-benzyl-N-(2-, 3 - or 4-methoxybenzyl)-amino, N-N-dibenzylamino, N-(2-, 3 - or 4-tibinil)-N-(2-, 3 - or 4-methoxybenzyl)-amino, N-(2-, 3 - or 4-oxybenzyl)-N-(2-, 3 - or 4-oxybenzyl)-amino, /bis-2 - or 3-furyl-methyl/-amino, /bis-2 - or 3-thienyl)-methyl/-amino, /1,1-bis-2 - or 3-thienyl)-ethyl/-amino, /(2 - or 3-methyl-2 or 3-thienyl), (2 - or 3-methyl-2 or 3-thienyl)-methyl/-amino, /1-(2 - or 3-methyl-)-1-methylethyl)-amino, /1-(2 - or 3-furyl-)-1-methylethyl)-amino, /1-(2 - or 3-methyl-2 or 3-thienyl)-1-methylethyl/-amino, /1-(2 - or 3-furyl-2-(2 - or 3-furyl)-ethyl/-amino, /1-(2 - or 3-thienyl-2-(2 - or 3-Tennille)-ethyl/-amino, /1-(2 - or 3-furyl-2-(2 - or 3-furyl)-ethyl/-amino, /1-(2 - or 3-thienyl-2-(2 - or 3-thienyl)-ethyl/-amino, /1-(2 - or 3-furyl-2-phenylethyl/-amino, /2-phenyl-1-(2-or 3-thienyl)-ethyl/-amino, /1-phenyl-2-(2 - or 3-Tennille)-ethyl/-amino, /2-(2-, 3- or 4-were)-1-(2 - or 3-thienyl)-ethyl/-amino, /2-(2-, 3- or 4-chlorophenyl)-1-(2 - or 3-thienyl)-ethyl/-amino, /2-(2-, 3- or 4-forfinal)-1-(2 - or 3-thienyl)-ethyl/-amino, /2-(2-, 3- or 4-methoxyphenyl)-1-(2 - or 3-thienyl)-ethyl/-amino, N-(2 - or 3-thienylmethyl)-N-(2 - or 3-thienylmethyl)-amino, /2-(2-, 3- or 4-forfinal)-2-(2 - or 3-thienyl)-ethyl/-amino, (2-hydroxy-1,2-diphenylether)-amino, N,N-diphenylhydrazone, N-(2-, 3 - or 4-methoxyphenyl)-N-phenylhydrazine, N-(2-, 3 - or 4-were)-N-phenylhydrazine, N-(2-, 3 - or 4-chlorophenyl)-N-phenylhydrazine, N-(2-, 3 - or 4-forfinal)-N-phenylhydrazine, N-(2-, 3 - or 4 oksifenil)-N-phenylhydrazine, N-(2-, 3 - or 4-acetamide is whether 4-methoxyphenyl)-hydrazine.

Most preferred of these include the following groups: (1-methyl-1-phenylethyl)-amino, (1-methyl-1-(2-, 3 - or 4-were)-ethyl/-amino, (1-methyl-1-(2-, 3 - or 4-methoxyphenyl)-ethyl/-amino, (1-methyl-1-(2-, 3 - or 4-chlorophenyl)-ethyl/-amino, (1-methyl-1-(2-, 3 - or 4-forfinal)-ethyl/-amino, (1-methyl-1-(2-, 3 - or 4-acetamidophenyl)-ethyl/-amino, (1,1-dimethyl-2-phenylethyl)-amino, benzhydrylamine, /(2-, 3 - or 4-), (2-, 3- or 4-)-diferensial/-amino, /(2-, 3 - or 4-), (2-, 3- or 4-)-dimethoxybenzamide/-amino, (2-, 3 - or 4-chlorobenzhydryl)amino, (2-, 3 - or 4-methoxybenzyl)-amino, (2-, 3 - or 4-farbenspiel)-amino, 2-, 3 - or 4-oxybenzyl)-amino, (1,1-diphenylether)amino, (1,2-diphenylether)-amino, /2-(2-, 3- or 4-chlorophenyl)-1-phenylethyl/-amino, /2-(2-, 3- or 4-forfinal)-1-phenylethyl/-amino, /2-(2-, 3- or 4-were)-1-phenylethyl/-amino, /2-(2-, 3- or 4-methoxyphenyl)-1-phenylethyl/-amino, N, N-dibenzylamino, N-2-, 3 - or 4-terbisil)-N-(2-, 3 - or 4-terbisil)-amino, N-2-, 3 - or 4-methylbenzyl)-N,N-(2-, 3 - or 4-methylbenzyl)-amino, N-2-, 3 - or 4-methoxybenzyl)-N-(2-, 3 - or 4-methoxybenzyl)-amino, /1-(2 - or 3-thienyl)-1-(2 - or 3-thienyl)-methyl/-amino, /2-phenyl-1-(2 - or 3-thienyl)-ethyl/-amino, /1-methyl-1-(2 - or 3-thienyl)-ethyl/-amino, /1-methyl-1-(2 - or 3-furyl)-ethyl/-amino, /1-methyl-1-(2 - or 5-methyl -, 2 - or 3-thienyl)-ethyl/-amino, (2-hydroxy-1,2-diphenylether)-amino, N, N)-hydrazine.

If the compounds according to the invention contain carboxypropyl or a phenolic oxygraph, they can form salts with bases. There are no special restrictions regarding the nature of these salts, provided that they are intended for therapeutic use and are pharmaceutically acceptable. Where they are intended for non-therapeutic use, for example, as intermediates for other, perhaps more active compounds, even this restriction does not apply. Examples of such salts include salts with alkali metals such as sodium, potassium or lithium: salts with alkaline earth metals such as barium or calcium: salts with other metals such as magnesium and aluminium salts of organic compounds, such salts as dicyclohexylamine and salts with basic amino acid such as lysine or arginine, of which the preferred salt with an alkaline metal.

Similarly, these acidic compounds can form esters, and there are also no restrictions regarding the nature of such esters, provided that they are intended for therapeutic use and are pharmaceutically acceptable connected is in, with aryl-substituted alkyl groups having 1 to 6 carbon atoms in the alkyl part, or alkenylamine groups having 3 to 6 carbon atoms, of which the preferred esters with alkyl group having 1 to 4 carbon atoms, benzyl group, with benzhydryl group or allyl group.

Compounds according to the invention can contain one or more asymmetric carbon atoms in their molecules, and thus can form optical isomers. Although all of them are represented here one molecular formula, but the invention includes as separate isomers and mixtures thereof, including racemates. If you use the methods of synthesis of stereoregular or use as a starting material an optically active compound, it can directly be obtained from the individual isomers; on the other hand, if the mixture of isomers, the individual isomers can be obtained by conventional methods of separation.

Preferred classes of compounds according to the invention are those compounds of formula I, their salts and esters, in which:

(A) R1represents a hydrogen atom, alkyl group having 3 carbon atomapi, including substituents (a) defined below, furylmethyl group or thienyl group, said substituents (a) selected from the group comprising alkyl groups having 1 to 4 carbon atoms, alkoxygroup having 1 to 4 carbon atoms, halogen atoms, actigraphy, alkoxycarbonyl group having 2 to 5 carbon atoms, and aliphatic carboxylic alluminare having 1 to 5 carbon atoms;

(C) R2represents a substituted alkyl group having 1 to 4 carbon atoms and substituted by at least one Deputy, selected from the group comprising phenyl groups, substituted phenyl groups having at least one Deputy, selected from the group including substituents (a) defined in paragraph (A), foreline group, foreline group, substituted C1-C4-alkyl Deputy, thienyl group and a thienyl group, substituted C1-C4-alkyl Deputy, these asilinae groups do not have more substituents or substituted by at least one Deputy, selected from the group including carboxypropyl and actigraphy;

diphenylamino from which each phenyl group is unsubstituted or one or both of E. in paragraph (A) above;

(C) R3represents a hydrogen atom, alkyl group having 1 to 4 carbon atoms, a substituted alkyl group having 1 to 4 carbon atoms and substituted by at least one Deputy, selected from the group comprising phenyl groups, substituted phenyl groups having at least one Deputy, selected from the group including substituents (a) defined in paragraph (A) above, carboxypropyl and actigraphy, or

alkenylphenol group having 3 to 4 carbon atoms;

(D) communication, presents alpha-beta, is a carbon-carbon simple relationship, and the relationship represented by gamma-Delta is a carbon-carbon simple bond or a carbon-carbon double bond, or a bond represented by alpha-beta, is a carbon-carbon double bond, and the bond represented by gamma-Delta is a carbon-carbon simple communication;

and of these, particularly preferred are those compounds in which R1matter specified in paragraph (A) above, R2matter specified in paragraph (B) above, R3matter specified in paragraph (C) above, and communications, presented the alpha beta and gamma Delta have the meaning as defined in paragraph (D) above.

Blognya esters, where:

(E) R1represents a hydrogen atom, an isopropyl group, benzyl group, substituted benzyl group having at least one Deputy, selected from the group including substituents (b), defined below, or trimethylene group, and said substituents (b) selected from the group including methyl group, ethyl group, metoxygroup, ethoxypropan, fluorine atoms, chlorine atoms, bromine atoms, actigraphy, ethoxycarbonyl group, methoxycarbonyl group, formamidine and acetaminop;

(F) R2represents a substituted alkyl group having 1 to 4 carbon atoms and substituted by at least one Deputy, selected from the group comprising phenyl groups, substituted phenyl groups having at least one Deputy, selected from the group including substituents (b), defined in paragraph (E) above, foreline group, substituted foreline groups with methyl Deputy, thienyl group and a substituted thienyl group, with methyl Deputy, with the aforementioned alkyl group have no further substituents or substituted by at least one axisymmetrical, or diphenylamino, in which Karim from the group including substituents (b), defined in paragraph (E) above;

(G) R3represents a hydrogen atom, methyl group, ethyl group, benzyl group, substituted benzyl group, which is substituted by at least one Deputy, selected from the group including substituents (b), defined in paragraph (E) above, substituted alkyl groups having 1 to 3 carbon atoms and substituted by at least one axisymmetrical or alkyl group; of these, particularly preferred compounds in which R1matter specified in paragraph (E) above, R2have the meanings given to it in clause (F) above, R3have the meanings given to it in clause (G) above, and especially those compounds in which in addition to the above relation, represented by the symbols of alpha beta and gamma Delta, have the meanings given to them in paragraph (D) above.

The most preferred classes of compounds according to the invention are those compounds of formula I, their salts and esters, in which:

(H) R1and R2the same or different and each represents a benzyl or substituted benzyl group having at least one Deputy, wybranie methyl group, metoxygroup, fluorine atoms, chlorine atoms, actigraphy and acetaminop;

(H') R1represents a hydrogen atom and R2represents a substituted alkyl group having 1 to 3 carbon atoms and substituted by at least one Deputy, selected from the group comprising phenyl groups, substituted phenyl groups having at least one Deputy, selected from the group including substituents (c) defined in paragraph (H) above, foreline group and thienyl group, or diphenylamino, in which each phenyl group is not substituted, or one or both groups substituted by at least one Deputy, selected from the group including substituents (c) defined in paragraph (H) above;

(I) R3represents a hydrogen atom, methyl group or ethyl group, and particularly preferred are those compounds in which R1and R2have the meanings given to them in clause (H) or (H') above, and R3matter specified in paragraph (I) above, and especially those in which in addition to the above relation, represented by the symbols of alpha beta and gamma Delta have the meanings defined in paragraph (D) above.

Alternative prudery, where:

(J) R1represents a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms or a substituted alkyl group having 1 to 6 carbon atoms which is substituted by at least one Deputy, selected from the group comprising aryl group, as defined below, an aromatic heterocyclic group, as defined below, and carboxypropyl;

(K) R2represents a substituted alkyl group having 1 to 6 carbon atoms which is substituted by at least one Deputy, selected from the group comprising aryl group, as defined below, and aromatic heterocyclic groups as defined below;

(L) R3represents a hydrogen atom, an unsubstituted alkyl group having 1 to 6 carbon atoms, a substituted alkyl group having 1 to 6 carbon atoms which is substituted by at least one Deputy, selected from the group comprising aryl group, as defined below, carboxypropyl and actigraphy;

(M) each of the connections represented as alpha-beta and gamma-Delta is a simple carbon-carbon bond or a double carbon-carbon bond;

the aforementioned aryl groups in paragraphs (J) (L) aany at least one Deputy, selected from the group comprising alkyl groups having 1 to 4 carbon atoms, alkoxygroup having 1 to 4 carbon atoms, actigraphy and halogen atoms;

mentioned aromatic heterocyclic group in paragraphs (J) and (K) have 5 to 6 ring atoms, of which one heteroatom selected from the group comprising heteroatoms of nitrogen, oxygen and sulfur, which is unsubstituted or substituted by at least one Deputy, selected from the group comprising alkyl group with 1 to 4 carbon atoms, alkoxygroup with 1 to 4 carbon atoms and halogen atoms; and especially preferred are those compounds in which R1matter specified in paragraph (J) above, R2have the meanings given to it in clause (K) above, and R3matter specified in paragraph (L) above, and in particular those compounds in which in addition to the above relation, represented as alpha-beta and gamma-Delta, have the meanings given to them in paragraph (M) above.

More preferred classes of compounds according to the invention are those compounds of formula I, their salts and esters, in which:

(N) R1represents a hydrogen atom, an unsubstituted alkyl group having meztitlan, selected from the group comprising phenyl groups, substituted phenyl groups having at least one Deputy, selected from the group comprising alkyl group with 1 to 4 carbon atoms, alkoxygroup having 1 to 4 carbon atoms, halogen and axisymmetrical, follow group and thienyl group;

(O) R2represents a substituted alkyl group having 1 to 4 carbon atoms and substituted by 1 to 3 substituents selected from the group comprising phenyl groups, substituted phenyl groups having at least one Deputy, selected from the group comprising alkyl groups having 1 to 4 carbon atoms, alkoxygroup having 1 to 4 carbon atoms, alkoxygroup having 1 to 4 carbon atoms, halogen atoms and actigraphy,

follow group or thienyl group;

(P) R3represents a hydrogen atom, alkyl group having 1 to 4 carbon atoms, a substituted alkyl group having 1 to 4 carbon atoms and having at least one Deputy, selected from the group comprising phenyl groups, carboxypropyl and actigraphy,

or alkenylphenol group having 3 or 4 carbon atom,

(Q) relation, represented as alpha-beta, is about the relationship or double carbon-carbon bond, or link represented alpha-beta, is a double carbon-carbon bond and a relationship represented as gamma-Delta is a carbon-carbon simple communication;

and of these, particularly preferred are those compounds in which R1have the meanings given to it in paragraph (N) above, R2matter specified in paragraph (A) above, and R3matter specified in paragraph (B) above, and in particular those in which (in addition) relationships represented as alpha-beta and gamma-Delta are those defined in paragraph (Q) above.

Much more preferred compounds according to the invention are those compounds of formula I, their salts and esters, in which:

(R) R1represents a hydrogen atom and R2represents a group of the formula

-C(CH3)(CH3)-R2',

in which R2'represent a phenyl group, substituted phenyl group having at least Deputy selected from the group comprising methyl, methoxy, chlorine atom, fluorine atom and hydroxy-substituents;

or substituted alkyl group having 1 to 3 carbon atoms and having 2 or 3 substituent selected from the group comprising Fenicia methyl, methoxy-, fluorine-, chlorine - and axisymmetrical,

foreline group and thienyl group, or

(R') R1and R2the same or different and each represents a substituted alkyl group having 1 to 3 carbon atoms and having one Deputy, selected from the group comprising phenyl groups, substituted phenyl groups having at least one Deputy, selected from the group comprising methyl, methoxy-, fluorine-, chlorine - and axisymmetrical,

foreline group and thienyl group;

(S) R3represents a hydrogen atom, methyl group, ethyl group, allyl group or benzyl group;

(T) the link represented through alpha-beta, is a carbon-carbon simple bond or a carbon-carbon double bond, and the bond represented through gamma-Delta is a carbon-carbon simple communication;

and of these, particularly preferred are those compounds in which R1and R2have the meanings defined in paragraph (R) or (R') above, R3matter specified in paragraph (S) above, and especially those compounds in which (in addition) communication presents alpha beta and gamma Delta have the meanings defined in paragraph (T) above.

N the formula I, their salts and esters, in which:

(U) R1represents a hydrogen atom and R2represents diphenylmethylene group, substituted diphenylmethylene group having at least one Deputy, selected from the group comprising methyl, methoxy, fluorine, chlorine or axisymmetrical;

1,2-diphenylethylene group, a substituted 1,2-diphenylethylene group having at least one Deputy, selected from the group comprising methyl, methoxy, fluorine, chlorine or axisymmetrical;

1,1-diphenylethylene group or a substituted 1,1-diphenylethylene group having at least one Deputy, selected from the group comprising methyl, methoxy, fluorine, chlorine or axisymmetrical;

(V) R3represents a hydrogen atom, methyl group or ethyl group;

of these are particularly preferred those compounds in which R1and R2have the meanings given to them in paragraph (U) above, R3matter specified in paragraph (U) above, and especially those compounds in which (in addition) relationships represented as alpha-beta and gamma-Delta are those defined in paragraph (T) above.

Examples of specific compounds according to the invention existing table. 1, 2 and 3, i.e. table. 1 relates to formula 1-1, PL. 2 to the formula 1-2, and table. 3 to the formula 1-3.

In table. 1 -3 used the following abbreviations for some groups of substituents: Ac is acetyl; All allyl; Bu butyl; Bz benzyl; Bzhy - benzhydryl; Bt ethyl; Fur furyl; Me is methyl; the Mec methoxycarbonyl; Ph is phenyl; Pr propyl; Thi thienyl.

Formula 1-1:

< / BR>
Formula 1-2:

< / BR>
Formula 1-3:

< / BR>
Listed in the table. 1 3 preferred compounds are compounds: 1-1, 1-2, 1-3, 1-4, 1-5, 1-11, 1-14, 1-16, 1-20, 1-22, 1-28, 1-32, 1-36, 1-38, 1-39, 1-44, 1-46, 1-47, 1-57, 1-58, 1-70, 1-74, 1-76, 1-81, 1-82, 1-85, 1-86, 1-88, 1-89, 1-95, 1-100, 1-101, 1-104, 1-107, 1-108, 1-09, 1-110, 1-111, 1-112, 1-113, 1-114, 1-115, 2-1, 2-2, 2-4, 2-5, 2-7, 2-8, 2-12, 2-14, 2-16, 2-17, 2-17, 2-18, 2-19, 2-20, 2-21, 2-23, 2-24, 2-26, 2-28, 2-29, 2-31, 2-33, 2-34, 2-35, 2-36, 2-42, 2-43, 2-44, 2-47, 2-48, 2-52, 2-54, 2-55, 2-56, 2-57, 2-59, 2-60, 2-61, 3-1, 3-2, 3-4, 3-5, 3-7, 3-8, 3-12, 3-14, 3-15, 3-16, 3-17, 3-18, 3-19, 3-20, 3-21, 3-23, 3-24, 3-38, 3-39, 3-31, 3-32, 3-33, 3-34, 3-35, 3-36, 3-42, 3-43, 3-45, 3-47, 3-50, 3-53, 3-54, 3-55, 3-56, 3-57 and 358 for.

Most preferred are compounds of rooms:

1-1. N-(1,2-diphenylether)-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide,

1-2. N-(1,2-diphenylmethyl)-3-oxo-3-Aza-5-alpha-androstane-17-beta-carboxamide,

1-3. N-(1,1-diphenylether)-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide,

1-22. N-/-2-(4-were)-1-phenylethyl/- 3-oxo-4-Aza-5-alpha-androstane-17,2-diphenylether)- 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide,

1-44. N-(1-methyl-1-phenylethyl)-3-oxo-4-Aza-5-alpha-androstane-17-beta-carbon - Samid,

1-45. N/(1-methyl-1-(2-thienyl)-ethyl/- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide,

1-46. N-/1-methyl-1-(2-thienyl)-ethyl/- 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide,

1-47. N-(1-methyl-1-phenylethyl) -4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide,

1-47. N-/2-(4-were-1-phenylethyl-4-methyl/ -3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide,

1-76. N-(1,1-diphenylether) -4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide,

1-81. N-(alpha-(4 oksifenil)-benzyl-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide,

1-82. N-(alpha-(4 oksifenil)- benzyl-4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide,

1-88. N-/1-(4-methoxyphenyl)-1-methylethyl/- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide,

1-89. N-/1-(4-methoxyphenyl)-1-methylethyl/ -4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide,

1-100. N,N-diphenyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide,

1-101. N,N-diphenyl-4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide,

1-104. N-/1-(3-methoxyphenyl-1-methylethyl/ -4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide,

1-114. N-/1-methyl-1-(2-furyl)-ethyl/ -3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide,

2-1. N-is-5-alpha-androstane-17-beta-carboxamide,

2-4. N-(diphenylmethyl) -3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide,

2-5. N-(diphenylmethyl) -4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide,

2-16. N-/1-phenyl-2-(methoxyphenyl)-ethyl/ -3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide,

2-17. N-/1-phenyl-2-(4-were)-ethyl/ -4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide,

2-18. N-(1,1-diphenylether) -3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide,

2-19. N-(1,1-diphenylether) -4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide,

2-20. N-(1-methyl-1-phenylethyl) -3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide,

2-21. N-(1-methyl-1-phenylethyl) -4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide,

2-23. N-/1-methyl-1-(-2-thienyl)-ethyl/ -3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide,

2-24. N-/1-methyl-1-(2-thienyl)-ethyl/ -4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide,

2-28. N/alpha oksifenil)-benzyl/ -3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide,

2-29. N/alpha(4 oksifenil)-benzyl/ -4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide,

2-35. N-/4-Methoxyphenyl)-1-2-methylethyl/ -3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide,

2-36. N-/1-(4-Methoxyphenyl)-1-methylethyl/ -4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carb is l-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta - carbohydrazide,

2-48. N, N-diphenyl-4-methyl-3-oxo-4-Aza-5-alpha-androst-1-EN-beta-carbohydrazide,

2-52. N-/1-(2-methoxyphenyl)-1-methylethyl/- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide,

2-60. N-/1-methyl-1-(2-furyl)-ethyl/- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide,

3-1. N-(1,2-diphenylether)- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide,

3-2. N-(1,1-diphenyl)- 4-methyl-3-oxo-4-Aza-5-ene-17-beta-carboxamide,

3-4. N-(diphenylmethyl)- 3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide,

3-5. N-(diphenylmethyl)- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide,

3-16. N-/2-(-4-were)-1-phenylethyl/- 3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide,

3-17. N-/2-(-4-were)-1-phenylethyl/- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide,

3-18. N-(1,1-diphenyl)- 3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide,

3-19. N-(1,1-diphenylether)- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide,

3-20. N-(1-methyl-1-phenylethyl)- 3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide,

3-21. N-(1-methyl-1-phenylethyl)- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide,

3-23. N-/1-methyl-1-(2-thienyl)-ethyl/- 3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide,

3-24. N-/1-methyl-1-(2-thienyl)-ethyl/- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide,

3-28. N/alpha(4 oksifenil)-benzyl/- 3-oxo-4 is-carboxamid,

3-35. N-/1-(4-methoxyphenyl)-1-methylethyl/- 3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide,

3-36. N-/1-(4-methoxyphenyl)-1-methylethyl/- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide,

3-45. N-(2-hydroxy-1,2-diphenylether)- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide,

3-47. N,N-diphenyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide,

3-48. N,N-diphenyl-4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide,

3-50. N-/1-(3-methoxyphenyl)-1-methylethyl/- 3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide,

3-53. N-/1-(2-methoxyphenyl)-1-methylethyl/- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide and

358 for. N-/1-methyl-1-(2-furyl)-ethyl)- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

Compounds according to the invention can be obtained by various methods known to experts in obtaining compounds of this type. For example, in General, they can be obtained:

a) interaction of the amino compounds of the formula II:

< / BR>
in which R1and R2have the meanings given above

with azasteroid derivative of the formula III:

< / BR>
in which W and W' together represent a group of formula IV:

< / BR>
or a group of formula IVa:

< / BR>
where alpha, beta, gamma, Delta, and R3have the meanings defined is inane, obtained in stage (a) to turn the group into a group of the formula IVb:

< / BR>
and the interaction of the compounds with the compound of the formula V: NH2R3,

in which R3has the above specified values,

to transform the group into a group of the formula IV:

C) if necessary, transformation groups represented by the radical R3in any other such group;

d) if necessary, converting the carbon-carbon simple communication presents alpha-beta, the carbon-carbon double bond;

e) if you wish, at any stage of obtaining salt or etherification of the compounds.

In more detail, these reactions can be carried out as follows.

Reaction (A):

< / BR>
In this reaction, the compound of formula I is produced by interaction azasteroid derivative of the formula IIIA or its reactive derivative with the compound of the formula II. If the compound of formula II contains one or more carboxylate, these carboxypropyl preferably protected before carrying out this reaction, using protective groups and reagents well-known in this field. Examples carboxyamide groups include tert-butyl, benzhydryl, 4-methylbenzhydryl and 4-the which can be applied for the synthesis of peptides such as the azide method, the method of activated esters, the method of mixed anhydrides of acids or condensation method.

After this reaction carboxyamide group can be removed by conventional means, depending on the nature of the protective group, for example by treatment of the compounds obtained by the acid in an inert solvent. Examples of acids that may be used include kaleidostone acid, such as hydrochloric acid, Hydrobromic acid, uudistoodetena acid and strong organic carboxylic acids and sulfonic acids, such as triperoxonane acid, trichloroacetic acid, triftoratsetata, of which the preferred organic acid. There are no special restrictions to the nature of the subject use of solvent provided that it does not have a negative impact on the course of the reaction or on the reagents involved in the reaction and that it can dissolve the reagents, at least to a certain extent. Examples of suitable solvents include halogenated hydrocarbons, especially halogenated aliphatic hydrocarbons, such as methylene chloride or chloroform, and arrowy ethers, such as anisole or doget take place in a wide range of temperatures and the precise reaction temperature is not critical to this invention. In General, it is convenient to conduct the reaction at a temperature of from -20oWith up to 50oS, more preferably from -10oWith up to room temperature. The time required for completion of the reaction, also varies widely depending on many factors, notably from the reaction temperature and the nature of the reagents. However, provided that the reaction is carried out in the preferred conditions outlined above, the period of time from 30 minutes to 20 hours and more preferably from one to 10 hours is usually sufficient.

Azide method.

Azide method may be carried out by the interaction of the compounds of formula IIIA or its complex ester with hydrazine in an inert solvent, such as dimethylformamide, at about room temperature to obtain the hydrazide amino acids, which can then be converted into the corresponding azide compound interaction with the connection of nitrous acid azide then subjected to interaction with aminoguanidinium formula II.

Examples of compounds of nitrous acid, which can be used include alkali metal nitrite such as sodium nitrite and alkalemia nitrites such as isoamyl nitrite.

The reaction preferably is carried out in which I provided that it does not affect adversely on the reaction or on the reagents involved in the reaction and that it can dissolve the reagents, at least to some extent. Examples of suitable solvents include amides, especially amides of fatty acids, such as dimethylformamide or dimethylacetamide, sulfoxidov, such as dimethyl sulfoxide and pyrrolidone, such as N-organic. Two stages of this method is usually carried out in one reaction solution without isolation of intermediate compounds. The reaction can take place in a wide range of temperatures and the precise reaction temperature is not critical for the invention. In General, it was found that it is convenient to conduct the reaction in the first stage at a temperature of from -50oWith 0oC, and the reaction in the second stage is at a temperature of from -10oTo +10oC. the Time required for the reaction may also vary widely, depending on many factors, including significantly from the reaction temperature and the nature of the reagents. However, based on the conditions that the reaction is performed in the preferred conditions outlined above, the period of time from 5 minutes to one hour and 10 hours to five days would be sufficient for the first stage and the second stage of the reaction, respectively which can be carried out by the interaction of the compounds of formula IIIA with etherification agent, to obtain an activated ester, and then by the interaction of the thus obtained activated complex ester with aminoguanidinium formula II.

Both reactions are preferably carried out in an inert solvent. There are no special restrictions to the nature of the solvent used in the reaction, provided that it does not affect adversely on the reaction or on the involved reagents and can dissolve the reagents, at least to some extent. Examples of suitable solvents include halogenated hydrocarbons, especially halogenated aliphatic hydrocarbons, such as methylene chloride or chloroform, ethers, such as diethyl ether or tetrahydrofuran, amides, especially amides of fatty acids, such as dimethylformamide or dimethylacetamide, and NITRILES, such as acetonitrile.

Suitable tarifitsiruemye agents that can be used in this reaction include N-oxycoedone, such as N-oxysuccinimide, 1-oxybisethanol and N-hydroxy-5-norbornene-2,3-dicarboximide and disulfide compounds such as dipyridamole. The reaction produce an activated complex ester is preferably carried out in the presence of a condensing agent is carried out in a wide range of temperatures and the precise reaction temperature is not critical for the invention. In General, it is convenient to conduct the reaction produce an activated complex ether at a temperature of from -10oWith up to 80oAnd the reaction of the activated ester with aminoguanidinium approximately at room temperature. The time required for the reaction may also vary widely, depending on many factors, among which is a noticeable reaction temperature and the nature of the reagents. However, provided that the reaction should be conducted at the preferred conditions of the above, the period of time from 30 minutes to 10 hours is usually sufficient for each reaction.

The method of mixed anhydrides of acids.

Get a mixed anhydride of the acid compounds of formula IIIA and then it is subjected to interaction with aminoguanidinium formula II.

The reaction of obtaining the mixed acid anhydride can be carried out by interaction of the acid compounds of formula IIIA with a compound capable of forming a mixed anhydride of the acid, such as halide carbonate alkyl with 1 to 4 carbon atoms, such as ethyl ether harpalinae acid or isobutyl ether harpalinae acid halide of lower alkanoyl, such as pivaloyl chloride, lower alkilany or allowin ether cyanophosphonate sour is usually and preferably carried out in an inert solvent, for example, in the above-mentioned halogenosilanes hydrocarbon, amide or simple ether.

The reaction is preferably carried out in the presence of an organic amine such as triethylamine or N-methylmorpholine.

The reaction can take place in a wide range of temperatures and the precise reaction temperature is not critical for the invention. In General, it's usually necessary to carry out the reaction at a temperature of from -10oWith up to 50oC. the Time required for the reaction also varies widely depending on many factors, such as the reaction temperature and the nature of the reagents. However, provided that the reaction is performed in the preferred conditions of the above, the period of time from 30 minutes to 20 hours will normally be sufficient.

The interaction of the thus obtained mixed acid anhydride with the amine of formula II is preferably carried out in an inert solvent, for example in the above-mentioned amide or simply ether, in the presence of an organic amine at a temperature of from 0oWith up to 80oC, at which the reaction usually requires 1 to 24 hours

This reaction can also be carried out by the interaction of both compounds of formula IIIA, connection fo the ionic method.

Condensation method can be performed by direct interaction of the compounds of formula IIIA with aminoguanidinium formula II in the presence of a condensing agent, such as dicyclohexylcarbodiimide, carbonyldiimidazole or iodine triethylamine 1-methyl-2-chloropyridine. The reaction is carried out analogously to the reaction used to obtain the above-mentioned activated complex ether.

Reaction B.

The compounds of formula I in which R3is R3a(where R3Arepresents a substituted or unsubstituted alkyl group or alkenylphenol group as defined for R3), i.e. the compound of formula IB can be obtained by the coupling of compounds of formula I in which R3Arepresents a hydrogen atom, i.e. a compound of formula IA with a compound of the formula:

R3aX (IIB),

where R3Ahas the previously defined values, X represents a halogen atom, preferably chlorine, bromine or iodine:

< / BR>
in which R1, R2, R3, R3aX, alpha beta and gamma Delta have the previously defined values.

The reaction is normally and preferably carried out in an inert solvent and in the presence of bases is their as sodium hydride or potassium hydride, the alcoholate of an alkali metal such as sodium methylate, sodium ethylate or tert-butyl potassium, hydroxide of alkali metal such as sodium hydroxide or potassium hydroxide and alkali metal carbonates such as lithium carbonate, sodium carbonate or potassium carbonate, of which the preferred hydrides of alkali metals.

To the nature of the solvent has no particular restrictions, provided that the solvent does not adversely affect the reaction or on the involved reagents and that it can dissolve the reagents, at least to a certain extent. Examples of suitable solvents include water, alcohols, such as methanol or ethanol, ethers, such as diethyl ether or tetrahydrofuran, aromatic hydrocarbons such as benzene, toluene or xylene, halogenated hydrocarbons, especially halogenated aliphatic hydrocarbons, such as methylene chloride or chloroform, ketones, such as acetone or methyl ethyl ketone, amides, especially amides of fatty acids, such as dimethylformamide, dimethylacetamide, triamide hexamethylphosphoric acid, sulfoxidov, such as dimethylsulfoxide and mixtures of any two or more of these solvents, of which the second solvent and water, can be conducted in a two-phase reaction in the presence of ammonium salts, such as hydrosulfite tetrabutylammonium.

The reaction can be carried out in a wide range of temperatures, and the precise reaction temperature is not critical for the invention. In General, it is convenient to conduct the reaction at a temperature of from -50oWith up to 150oWith (more preferably from -10oWith up to 100oC). The time required for the reaction also varies within wide limits depending on many factors, notably from the reaction temperature and the nature of the reagents. However, provided that the reaction is performed in the preferred conditions outlined above, the period of time from 30 minutes to 24 hours (more preferably 1 to 10 h) is usually sufficient.

The source material of the formula IIIA is a known compound or can be obtained by a known method, for example, J. Med. Chem. 27, 1960 (1984): 29, 2298 (1986).

Starting material of formula II is a known compound or can be obtained by a known method such as Synthesis, 593 (176), I. Ord. Chem. 36, 305 (1971), Angew. Chem. 82, 138 (1970), 24 (1978), Senthesis Commun 17, 777 (1988), Senthesis Commun 18, 783 (1988), Organic Reation 3, 337 (1946), Org. Synthesis 51, 48, Tetrahidrom 30, 2151 (1974) and I. Org. Chem. 37, 188, (1972).

Reaction C.

< / BR>
in which R1, R is formula (IC), which is a compound of formula I, in which the 1,2-bond is a double bond, get dehydrogenization the compounds of formula Ib, in which 1,2-link is a simple link used any of the following four methods.

1). Dehydrogenase 2,3-dichloro-5,6-dicyano-parabenzoquinone.

The interaction of the compounds of formula Ib with 2,3-dichloro-5,6-dicyano-parabenzoquinone can be carried out in an inert solvent and in the presence of the agent, to introduce a silyl group.

Examples of reagents which introduce silyl group include: amides of bis-/(Tris-C1-C4)-carboxylic acids, such as N,O-bis(trimethylsilyl)-ndimethylacetamide, N,O-bis(trimethylsilyl)-ndimethylacetamide, N,O-bis-(Tripropylene)-ndimethylacetamide, N, O-bis-(tributyltin)-ndimethylacetamide, N,O-bis(trimethylsilyl)-triptorelin, N, O-bis-(triethylsilyl)-triptorelin, N,O-bis-(Tripropylene)-triptorelin, N,O-bis-(tributyltin)-triptorelin, N,O-bis(trimethylsilyl)-pentafluoropropionate, N,O-bis-(triethylsilyl)-pentafluoropropionate, N,O-bis-(Tripropylene)-pentafluoropropionate, N,O-bis-(tributyltin)-pentafluoropropionate, N, O-bis(trimethylsilyl)-trichloroacetamide, N, O-bis-(triethylsilyl)-trichloroacetamide, N,O-bis-(Tripropylene)-trichloroe(triethylsilyl)-triptorelin, N, O-bis(trimethylsilyl)-pentafluoropropionate and N,O-bis-(triethylsilyl)-pentafluoropropionate,

and more preferably N,O-bis(trimethylsilyl)-triptorelin and N,O-bis-(triethylsilyl)-triptorelin.

To the nature of the solvent has no particular restrictions, provided that the applied solution does not affect adversely on the reaction or on the reagents involved in the reaction and that it can dissolve the reagents, at least to some extent. Examples of suitable solvents include ethers, such as diethyl ether, tetrahydrofuran and dioxane: hydrocarbons, which may be aliphatic or aromatic, such as hexane, benzene, toluene, xylene and cyclohexane, and halogenated hydrocarbons, especially halogenated aliphatic hydrocarbons, such as methylene chloride, chloroform and carbon tetrachloride. Of these solvents, preferred ethers.

The reaction may proceed in a wide range of temperatures and the precise reaction temperature is not critical for the invention. In General, it is convenient to conduct the reaction at a temperature of from 0oWith up to 150oS, more preferably from room temperature to 120oC. Time, need to change the x significant are the reaction temperature and the nature of the reagents. However, provided that the reaction is carried out in the preferred conditions outlined above, the period of time from 1 h to 24 h, more preferably 3 to 20 hours, is usually sufficient.

2) Dehydrogenase anhydride benzylamino acid.

Oxidation of compounds of formula Ib can be carried out in an inert solvent in the presence of the anhydride benzylamino acid.

To the nature of the solvent has no particular restrictions, provided that it does not affect adversely on the reaction or on the involved reagents and can dissolve the reagents, at least to some extent. Examples of suitable solvents include aromatic hydrocarbons, and halogenated aromatic hydrocarbons such as benzene, toluene, xylene, chlorobenzene and dichlorobenzene: dialkylamide, such as dimethylformamide and dimethylacetamide and diallylsulfide, such as dimethylsulfoxide. Of these preferred aromatic hydrocarbons.

The reaction can take place in a wide range of temperatures and the precise reaction temperature is not critical for the invention. In General, it is convenient to conduct the reaction at a temperature of from 50oWith up to 250oS, more preferably from 100joi by many factors, to a large extent on the reaction temperature and the nature of the reagents. However, provided that the reaction is performed in the preferred conditions outlined above, the period of time from 2 h to 24 h, preferably 2 to 10 hours is usually sufficient.

3) Deionisation.

It is conducted in three stages:

i) Reaction of the compound Ib with veridicality.

This reaction is carried out in an inert solvent in the presence of a base.

Examples of suitable duringsleep include diphenyldisulfide, ditertiary, deproliferation, diphemethoxidine and disaffiliative, preferably diphenyldisulfide.

Examples of suitable bases include amides Valkyrie, such as diisopropylamide lithium, dicyclohexylamine lithium and isopropylcyclohexane lithium, preferably diisopropylamide lithium.

Does not impose special restrictions to the nature of the solvent, provided that the latter does not affect adversely on the reaction or on the involved reagents and that it can dissolve the reagents, at least to some extent. Examples of suitable solvents include ethers, such as diethyl ether, tetrahydrofuran and dioxane, and ug is clohexane. Of them preferred ethers.

The reaction can take place in a wide range of temperatures and the precise reaction temperature is not critical for the invention. In General, it is convenient to conduct the reaction at a temperature of from -78oWith up to 50oS, more preferably from -30oWith up to room temperature. The time required for the reaction also varies within wide limits depending on many factors, significantly on the reaction temperature and the nature of the reagents. However, based on the conditions of the reaction in the preferred conditions outlined above, a period of time from 1 h to 24 h, more preferably 3 to 24 hours is usually sufficient.

ii) the Oxidation of sulfide.

The oxidation reaction of the sulfide obtained in stage (i) can be carried out in an inert solvent in the presence of an oxidant.

Examples of suitable oxidants include percolate, such as peracetic acid, natantia acid, natalilove acid and metaglidasen acid and perhalogenated alkali metal such as sodium perchlorate, potassium perchlorate, perbromic sodium, periodate lithium, periodate sodium and periodate potassium. Which one is preferable natantia acid, Armenia to the nature of the solvent provided that it does not affect adversely on the reaction or on the reagents involved in the reaction and can dissolve the reagents, at least to some extent. Examples of suitable solvents include alcohols, such as methanol, ethanol, propanol and butanol, hydrocarbons, which may be aliphatic or aromatic, such as hexane, benzene, toluene, xylene and cyclohexane, and halogenated hydrocarbons, especially halogenated aliphatic hydrocarbons, such as methylene chloride, chloroform and carbon tetrachloride, are preferred alcohols.

The reaction can take place in a wide range of temperatures and the precise reaction temperature is not critical for the invention. In General, it is convenient to conduct the reaction at a temperature of from -20oWith up to 50oS, more preferably from 0oWith up to room temperature. The time required for the reaction may also vary widely, depending on many factors, significantly on the reaction temperature and the nature of the reagents. However, with the reaction in the preferred conditions outlined above, a period of time of 1 to 24 hours, more preferably 3 to 20 hours, is usually sufficient.

iii) Deionisation.

There are no special restrictions regarding the nature of the solvent, provided that it does not affect adversely on the reaction or on the participating agents, and that it can dissolve the reagents, at least to a certain extent. Examples of suitable solvents include aromatic hydrocarbons and halogenated aromatic hydrocarbons such as benzene, toluene, xylene and chlorobenzene, dialkylamide, such as dimethylformamide and dimethylacetamide and diallylsulfide, such as dimethylsulfoxide. Which one is preferable aromatic and halogenated aromatic hydrocarbons.

Examples of bases are the same, which is shown in stage 4 (i) below.

The reaction can take place in a wide range of temperatures and the precise reaction temperature is not critical for the invention. In General, it is convenient to conduct the reaction at a temperature of from 50oWith up to 250oS, more preferably from 100oWith up to 200oC. the Time required for the reaction may also vary within wide limits depending on many factors, most notably from the reaction temperature and the nature of the reagents. However, when the reaction is preferable in the method dihydrobromide acid.

The method is carried out in 4 stages.

i) Reaction of the compound Ib with halide accelerom.

The reaction can be carried out in an inert solvent in the presence of organic bases.

Examples of suitable halide of xalilov include oxalicacid and oxalipatin, preferably chloride, oxalyl.

Examples of suitable organic bases include triethylamine, diethylaniline, pyridine, 4-dimethylaminopyridine, 1,5-diazabicyclo-/4,3,0)-non-5-ene and 1,8-diazabicyclo-/5,4,0/-indec-7-ene, preferably triethylamine, diethylaniline or pyridine.

On the nature of the subject to the application of the solvent has no particular restrictions, provided that it does not affect adversely on the reaction or involved in the reaction reagents and can dissolve the reagents, at least to some extent. Examples of suitable solvents include ethers, such as diethyl ether, tetrahydrofuran and dioxane, hydrocarbons, which may be aliphatic or aromatic, such as hexane, benzene, toluene, xylene and cyclohexane, and halogenated hydrocarbons, especially halogenated aliphatic hydrocarbons, such as methylene chloride, chloroform, tetrachloride and rotor and the precise reaction temperature is not critical for the invention. In General, it is convenient to conduct the reaction at a temperature of from -20oWith up to 100oS, more preferably from 0oWith up to room temperature. The time required for the reaction also varies within wide limits depending on many factors, to a large extent on the reaction temperature and the nature of the reagents. However, with the reaction in the preferred conditions outlined above, a period of time from 30 min to 10 h, more preferably 1 to 5 h usually is enough.

ii) Bromination of oxalate.

Bromination of oxalate obtained in stage (i) may be carried out by the interaction with bromine in an inert solvent.

On the nature of the solvent is not imposed special restrictions, provided that subject to the application of the solvent does not adversely affect the reaction or on the reagents involved in the reaction and can dissolve the reagents, at least to some extent. Examples of suitable solvents include ethers, such as diethyl ether, tetrahydrofuran and dioxane, which may be aliphatic or aromatic, such as hexane, benzene, toluene, xylene and cyclohexane, and halogenated hydrocarbons, in hilarity carbon. Of these solvents, preferred halogenated hydrocarbons.

The reaction may proceed in a wide range of temperatures and the precise reaction temperature is not critical for the invention. In General, it is convenient to conduct the reaction at a temperature of from -20oWith up to 50oS, more preferably from 0oWith up to room temperature. The time required for the reaction may also vary within wide limits depending on many factors, among which significant reaction temperature, the nature of the reagents. However, with the reaction in the preferred conditions outlined above, a period of time from 30 min to 24 h, more preferably from 1 to 10 hours will normally suffice.

iii) Desexualization.

The reaction can be carried out in an inert solvent in the presence of Ethylenediamine.

To nature subject to application of solvent is not subject to special restrictions, provided that it does not affect adversely on the reaction or on participating in the reaction reagents and that it can dissolve the reagents, at least to some extent. Examples of suitable solvents include ethers, such as diethyl ether, tetrahydrofur lool, xylene and cyclohexane, and halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride. Of these solvents, preferred ethers.

The reaction may proceed in a wide range of temperatures and the precise temperature is not critical for the invention. In General, it is convenient to conduct the reaction at a temperature of from 0oWith up to 200oS, more preferably from room temperature to 100oC. the Time required for the reaction may also vary widely, depending on many factors, among them significant are the reaction temperature and the nature of the reagents. However, given that the reaction is performed in the preferred conditions outlined above, a period of time from 30 min to 24 h, more preferably 1 to 10 hours is usually sufficient.

iv) Dehydrobrominated.

Dehydrobrominated bromide obtained in stage (iii) can be carried out in an inert solvent in the presence of organic bases.

Examples of suitable organic bases include triethylamine, diethylaniline, pyridine, 4-dimethylaminopyridine, 1,5-diazabicyclo-/4,3,0)-non-5-ene (DBN) and 1.8-diazabicyclo-/5.4.0/-undec-7-ene (DBU), Predela provided that it does not affect adversely on the reaction or on the involved reagents and can dissolve the reagents, at least to a certain extent. Examples of suitable solvents include ethers, such as diethyl ether, tetrahydrofuran, dioxane, hydrocarbons, which may be aliphatic or aromatic, such as hexane, benzene, toluene, xylene and cyclohexane, and halogenated hydrocarbons, especially halogenated aliphatic hydrocarbons, such as methylene chloride, chloroform and carbon tetrachloride. Of these solvents, preferred ethers or hydrocarbons.

The reaction can be performed in a wide range of temperatures and the precise reaction temperature is not critical for the invention. In General, it is convenient to conduct the reaction at a temperature of from -20oWith up to 100oS, more preferably from 0oWith up to 50oC. the Time required for the reaction may also vary within wide limits depending on many factors, essentially on the reaction temperature and the nature of the reagents. However, provided that the reaction is performed in the preferred conditions outlined above, a period of time from 30 min to 10 h, more preferably 1 to 5 h, is an Association of the formula I, in which the link 5, 6 is a double bond, can be obtained by the coupling of compounds of formula VI with aminoguanidinium formula V in an inert solvent.

There is no particular restriction on the nature of the subject to the application of the solvent, provided that it does not affect adversely on the reaction or on the involved reagents and which can dissolve the reagents, at least to some extent. Examples of suitable solvents include glycols such as ethylene glycol and propylene glycol, dialkylamide, such as dimethylformamide and dimethylacetamide, diallylsulfide, such as dimethyl sulfoxide and ethers such as dimethyl glycol, dimethyl ether of propylene glycol, diethyl ether of ethylene glycol and diethyl ether of propylene glycol. Of these solvents, preferred glycols.

The reaction can take place in a wide range of temperatures and the precise reaction temperature is not critical for the invention. In General, it is convenient to conduct the reaction at a temperature of from -10oWith up to 220oWith, preferably raising the temperature in the range -10oWith up to 150oC for 2 5 h and then maintaining the reaction mixture at a temperature of from 150oWith up to 220oSince t is to be obtained by the coupling of compounds of formula VII:

< / BR>
which is described in I. Med. Chem. 27, 1690, 1701, (1984) and 29, 2298 2315 (1985).

with aminoguanidinium formula II:

< / BR>
in a similar manner to that described in reaction A, with subsequent oxidation method similar to that described in I. Med. Chem. 27, 1690 1701 (1984) and 29, 2298 2315 (1986).

After completion of all stages of the reaction the desired connection with this stage can be isolated from the reaction mixture by conventional means. For example, in one suitable method of separation of the reaction mixture is appropriately neutralized, insoluble materials, if any, are removed by filtration, the solvent is distilled off, then the crystals are separated, remove the filter and get the desired compound; or the reaction mixture is diluted with water, extracted with water-immiscible organic solvent, the solvent is distilled off and get the desired connection. If necessary, the compound may be further purified by traditional means such as recrystallization, re-precipitation or various chromatographic methods, especially column chromatography.

Azasteroid compounds according to the invention have a pronounced ability to inhibit testosterone-5-alpha-rechazo and Nata.

For this purpose, they can be, if required, used in a mixture with other active compounds and/or with conventional carriers, diluents, auxiliary and/or fillers for the preparation of pharmaceutical preparations. Alternatively, they can, if required, be entered alone. The form of the medicinal product, of course, will depend on the selected route of administration, but for oral administration the compounds can be, for example, prepared in the form of powders, granules, syrups, tablets, or capsules; for parenteral administration they may be prepared in the form of injections, suppositories or inhalation. These drugs can be obtained by known methods by adding additives such as carriers, binders, shredders, lubricants, stabilizers and substances that improve the taste of drugs. Although the dose may vary depending on the symptoms and age of the patient, nature and severity of the disease or disorder, the route and method of administration, in the case of oral administration to an adult patient can usually be entered daily dose of 1 to 1000 mg of the Compounds can be administered in a single dose or fractional doses, for example two or three times a day.

Receipt and scope of the invention, and getting some of the original materials used in these examples are shown in the following examples of the preparation of starting materials.

Example 1. N-(diphenylmethyl)-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

100 g of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid, 100 ml of diphenylethylamine, 75 ml of diethyl ether cyanophosphonate acid and 100 ml triethylamine were added in this order to 5 ml of dry methylene chloride and then the reaction solution was left overnight under stirring at room temperature. Then it was diluted with 100 ml of methylene chloride and washed with 1 N. aqueous hydrochloric acid, water, aqueous sodium bicarbonate solution and saturated aqueous sodium chloride in this order, dried over anhydrous magnesium sulfate and person to distil under reduced pressure. The obtained residue was purified column chromatography through 15 g of silica gel. Gradient elution with a mixture acetonitrile methylene within relations from 1 9 to 1 1 by volume received 137 mg specified in the title of the example target compound.

Spectrum of nuclear magnetic resonance (CDCl3Delta, mn doctor of 0.67 (3H, singlet), of 0.90 (3H, singlet), 0,70 2,00 (15 NM, multi is J 9 Hz), 6,28 (1H, doublet, J 9 Hz), 7,20 7,38 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3288, 2935, 2868, 1664, 1521, 1493, 1448, 1226, 733, 698,

Example 2. N-(1,1-diphenylether)-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

150 ml of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid, 250 ml of 1,1-diphenylethylene, 150 mg iodide, 2-chloro-1-methylpyridine and 150 ml of triethylamine were dissolved in 5 ml of dry acetonitrile and the solution was heated for 4 h under reflux. At the end of this time the reaction solution was diluted with 100 ml of methylene chloride, washed with 1 N. aqueous hydrochloric acid, water, aqueous solution of sodium bisulfate and saturated aqueous solution of sodium chloride in the order listed and dried over anhydrous magnesium sulfate, then the solvent was removed by distillation under reduced pressure. The obtained residue was purified chromatographically on a column of 15 g of silica gel. Gradient elution with mixtures acetonitrile methylene within relations from 1 9 to 1 1 by volume received 165 mg of the target compound.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0,70 (3H, singlet), of 0.90 (3H, singlet), of 2.20 (3H, singlet), 0,70 2,25 (17H, multiplet), 2,35 2,50 (3H, multiplepoint (KBr),maxcm-1: 3300, 2937, 1665, 1491, 1446, 1360, 1226, 762, 699.

Example 3. N-(1,2-diphenylether)-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

Indicated in the name of the target compound with a yield of 91 was obtained by the method similar to that described in example 1, by reacting 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid and 1,2-diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.48 and 0.50 (all 3H, each singlet), 0.88 and 0.89 as (all 3H, each singlet), 0,7 2,2 (M, multiplet), 2,35 2,47 (2H, multiplet), 2,97 3,30 (3H, multiplet), 5,20 ceiling of 5.60 (3H, multiplet), 7,02 7,37 (N, multiplet).

Absorption spectrum in the infrared region (KBr), maxcm-1: 3300, 2935, 1664, 1525, 1495, 1358, 1307, 1227, 755, 698.

Example 4. N,N-dibenzyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

Indicated in the name of example, the target compound with a yield of 79 was obtained in a manner analogous to the method in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid and N,N-dibenzylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.89 (3H, singlet), of 0.91 (3H, singlet), 0,7 1,9 (17H, multiplet), of 2.3 to 2.5 (2H, multiplet), 2,73 (1H, triplet, J 8 Hz), 3,03 (1H, double doublet, J 10 and 5 Hz), to 3.73 (1H, LASS="ptx2">

Absorption spectrum in the infrared region (KBr),maxcm-1: 2196, 2933, 1669, 1633, 1444, 1359, 1306, 1218, 755, 703.

Example 5. N-(2,2-diphenylether)-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

Indicated in the name of example, the target compound with a yield of 81 was obtained in a manner analogous to the one described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid and 2,2-diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.54 (3H, singlet), to 0.88 (3H, singlet), 0,73 2,20 (17H, multiplet), a 2.36 - of 2.54 (2H, multiplet), of 3.00 (1H, doublet of doublets, J 10 and 5 Hz), of 3.48 (1H, doublet, J 5 Hz), 3,74 (1H, double doublet of doublets, J 15, 10 and 5 Hz), 4,07 (1H, double doublet of doublets, J 15, 10 and 5 Hz), is 4.21 (1H, triplet, J 10 Hz), 5,20 (1H, broad triplet, J 5 Hz), 5,42 (1H, broad), 7.18 in 7,37 (10H, triplet).

Absorption spectrum in the infrared region (KBr)maxcm-1: 3282, 3189, 2934, 1662, 1494, 1449, 1357, 1229, 735, 701.

Example 6. N-(3,3-diphenylpropyl)-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The target compound is indicated in the name of the example was obtained with 95-s ' output method similar to that described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid and 3,3-diphenylpropylamine.

JV the years), 2,22 - of 2.34 (2H, multiplet), 2,36 2,47 (2H, multiplet), was 3.05 (1H, doublet of doublets, J 10 and 5 Hz) at 3.25 (2H, multiplet), of 3.97 (1H, triplet, J 8 Hz), 5,20 (1H, broad triplet, J 6 Hz), vs. 5.47 (1H, broad), 7,13 to 7.35 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3305, 2935, 2869, 1662, 1532, 1449, 1359, 1307, 1227, 750, 701.

Example 7.

Target connection specified in the title of the example was obtained from 54 output method similar to that described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid with diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days is 0.69 (3H, singlet), of 0.97 (3H, singlet), 0,80 2,30 (N, multiplet), and 3.31 (1H, triplet, J 10 Hz), 5,20 (1H, broad), 5,80 (1H, doublet, J 9 Hz), of 5.89 (1H, doublet, J 8 Hz), 6,28 (1H, doublet, J 8 Hz), 6,77 (1H, doublet, J 9 Hz), 7,10 7,40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2935, 1676. 1600, 1518, 1493, 1448, 698.

Example 8. N-(1,2-diphenylether)- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example was obtained from 87 output method similar to that described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid 1,2-diphenylethylamine.

Absorption spectrum in the infrared region (KBr),maxcm-1: 2968, 1675, 1601, 1525, 1495, 1452, 816, 698.

Example 9. N,N-Dibenzyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example was obtained with the yield 58 manner similar to that described in example 1 1, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid with N,N-dibenzylamino.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.90 (3H, singlet), 0,99 (3H, singlet), 0,0 1,95 (14N, multiplet), is 2.40 (1H, Quartet, J 10 Hz), was 2.76 (1H, triplet, J 9 Hz), 3,30 (1H, triplet, J 9 Hz), of 3.77 (1H, doublet, J 14 Hz), 4,18 (1H, doublet, J 16 Hz), the 4.90 (1H, doublet, J 16 Hz), from 5.29 (1H, broad), the 5.45 (1H, doublet, J 14 Hz), 5,80 (1H, doublet, J 10 Hz), 6,74 (1H, doublet, J 10 Hz), 7,00 7,40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2938, 1682, 1636, 1444, 1423, 699.

Example 10. N-(2,2-diphenylether)-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide

The connection specified in the title of the example, with the release of 90 was obtained by way analogically.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.56 (3H, singlet), of 0.95 (3H, singlet), 0,80 2,20 (N, multiplet), 3,29 (1H, triplet, J 9 Hz), 3,74 (1H, multiplet), 4,08 (1H, multiplet), is 4.21 (1H, triplet, J 8 Hz), to 5.21 (1H, broad triplet), 5,31 (1H, broad), 5,80 (1H, doublet, J 10 Hz), 6,76 (1H, doublet, J 10 Hz), 7,10 7,40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3296, 2933, 1675, 1600, 1517, 1594, 1450, 1226, 816, 700.

Example 11. N-(diphenylmethyl)-3-oxo-4-Aza-5-alpha-androst-5-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 59 was obtained in a manner analogous to the one described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androst-5-ene-17-beta-carboxylic acid with diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.71 (3H, singlet), 1,10 (3H, singlet), 1,00 2,00 (N, multiplet), 2,40 - to 2.55 (2H, multiplet), 4,79 (1H, multiplet), of 5.89 (1H, doublet, J 9 Hz), 6,28 (1H, doublet, J 9 Hz), 7,16 (1H, broad), 7.18 in yield of 7.40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 1661, 1485, 1400, 700.

Example 12. N-(1,2-diphenylether)- 3-oxo-4-Aza-5-alpha-androst-5-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 68 received sposoby and 1,2-diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0.50 to 0.53 (all 3H, each singlet), with 1.07 and 1.09 (all 3H, each singlet), 1,00 2,30 (N, multiplet), 2,40 2,60 (2H, multiplet), 2,98 up 3.22 (2H, multiplet), 4,78 (1H, multiplet), 5,23 of 5.40 (1H, multiplet), 5,50 and ceiling of 5.60 (all 1H, each doublet, J 9 Hz), 7,00 7,40 (11N, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3186, 2942, 1662, 1604, 1492, 1386, 1221, 768, 699.

Example 13. N,N-dibenzyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

The target compound was obtained with the yield 71 manner similar to that described in example 1, the interaction of 3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid with N,N-dibenzylamino.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.93 (3H, singlet), of 1.12 (3H, singlet), 1,00 2,50 (17H, multiplet), 2,676 (1H, triplet, J 9 Hz in), 3.75 (1H, doublet, J 14 Hz), 4,17 (1H, doublet, J 16 Hz), 4,79 (1H, multiplet), the 4.29 (1H, doublet, J 16 Hz), 5,46 (1H, doublet, J 14 Hz), 7,00 7,4 (11N, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3200, 2936, 1729, 1664, 1360, 1193, 1182, 1155.

Example 14. N-(1,1-Dimethyl-2-phenylethyl)- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example with the release of 12 was obtained in a manner analogous to the-phenethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0,70 (3H, singlet), of 0.90 (3H, singlet), of 1.27 (3H, singlet), USD 1.43 (3H, singlet), 0,75 2,30 (N, multiplet), 2,37 of 2.50 (2H, multiplet), and 2.83 (1H, doublet, J 13 Hz), 3,05 (1H, doublet of doublets, J 10 and 5 Hz), 3,20 (1H, doublet, J 13 Hz), of 5.53 (1H, broad), 7,10 to 7.35 (5H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2937, 2869, 1666, 1502, 1452, 1385, 1360, 1307, 1229, 727, 702.

Example 15. N-(1,1-dimethyl-2-phenylethyl) -3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

Indicated in the name of example, the connection with the release of 48 was obtained by the method similar to that described in example 2, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid and 1,1-dimethyl-2-phenethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0,70 (3H, singlet), is 0.96 (3H, singlet), of 1.27 (3H, singlet), of 1.44 (3H, singlet), from 0.90 to 2.25 (M, multiplet), 2,82 (1H, doublet, J 13 Hz), 3,20 (1H, doublet, J 13 Hz), 3,32 (1H, triplet, J 9 Hz), equal to 4.97 (1H, broad), of 5.40 (1H, broad), 5,80 (1H, doublet, J 10 and 1 Hz), 6,77 (1H, doublet, J 10 Hz), 7,10 to 7.35 (5H, multiplet).

Absorption spectrum in the infrared region (KBr), maxcm-1: 2968, 2944, 168, 1600, 1503, 1452, 1362, 702.

Example 16. N-benzyl-N-isopropyl-3-oxo-4-Aza-5-alpha-androst-17-beta-carboxamide.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0,70 2,90 (N, multiplet) to 3.02 (1H, multiplet), 4,20 and 4,29 (all 1H, each doublet, J 15 and 17 Hz), 4,40 and 4,96 (all 1H, each singlet, J 7 Hz), 4,82 and 4,84 (all 1H, each doublet, J 17 and 15 Hz), of 5.40 (1H, broad), 7,10 yield of 7.40 (5H, multiplet).

Absorption spectrum in the infrared region (KBr), maxcm-1: 2970, 2937, 1668, 1451, 1418, 1388, 1360, 1307, 732.

Example 17. N-benzyl-N-isopropyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The target compound is indicated in the name of example, with an output of 40 was obtained by the method similar to that described in example 2, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid with N-benzyl-N-isopropylamino.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0,70 2,40 (N, multiplet), 2.48 and 2,84 (all 1H, each triplet, J 9 Hz), 3,23 3,40 (1H, multiplet), 4,22 and 4,30 (all 1H, each doublet, J 15 and 17 Hz), and 4,40 4,95 (all 1H, each septet, J 7 Hz), 4,80, and a 4.83 (all 1H, each doublet, J 17 and 15 Hz), and 5.30 (1H, broad), and 5.30 (1H, multiplet), 6,75 and 6.78 (all 1H, each doublet, J 9 Hz), 7,10 yield of 7.40 (5H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3197, 2971, 2934, 1681, 1636, 1602, 1450, 1417, 1366, 1180, 817, 697.

Example 18. N-(1,1-diphenylether)- 3-oxo-4-Aza-5-alpha-and abom, similar to that described in example 2, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid 1,1-diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0,70 (3H, singlet), and 0.98 (3H, singlet), 0,90 2,30 (N, multiplet), of 2.20 (3H, singlet), to 3.33 (1H, triplet, J 9 Hz), 5,32 (1H, broad), 5,80 (1H, doublet, J 10 Hz), 5,98 (1H, singlet), is 6.78 (1H, doublet, J 10 Hz), 7,10 - 7,40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2968, 2935, 1678, 1600, 1491, 1446, 1365, 761, 699.

Example 19. N-(1,1-diphenylether)- 3-oxo-4-Aza-5-alpha-androst-5-ene-17-beta-carboxamide.

Indicated in the name of example, the target compound with a yield of 55 was obtained by the method similar to that described in example 2, the interaction of 3-oxo-4-Aza-5-alpha-androst-5-ene-17-beta-carboxylic acid and 1,1-diphenylethylene.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days to 0.73 (3H, singlet), is 1.11 (3H, singlet), 1,00 2,30 (N, multiplet), of 2.20 (3H, singlet), 2,40 2,55 (2H, multiplet), 4,80 (1H, multiplet), 5,98 (1H, broad), 7,10 7,40 (11N, multiplet).

Absorption spectrum in the infrared region (KBr), maxcm-1: 2943, 1681, 1667, 1487, 1447, 1386, 669.

Example 20. N-(diphenylmethyl)- 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carbox is described in example 1, was dissolved in 4 ml of dry dimethylformamide and the resulting solution was added 40 mg of sodium hydride (as a 55 weight suspension in mineral oil). Then the mixture was stirred at room temperature for 30 min and was added dropwise thereto 0.5 ml iodotope bromide at room temperature, then the mixture was stirred at 70o2 hours after this time the reaction solution was diluted with 200 ml diethyl ether, three times washed with water, then saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. Then solvent was removed by distillation under reduced pressure. The obtained residue was purified column chromatography through 15 g of silica gel. Gradient elution with a mixture acetonitrile methylene within relations from 1 20 to 1 4 to get the 106 mg of the target compound.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.67 (3H, singlet), to 0.88 (3H, singlet), 0,70 2,50 (20N, multiplet), with 2.93 (3H, singlet), to 3.02 (1H, doublet of doublets, J 12 and 2 Hz), 5,88 (1H, doublet, J 8 Hz), of 6.29 (1H, doublet, J 8 Hz), 7,10 was 7.45 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3296, 2937, 1665, 1619, 1528, 1493, 1446, 1397, 1304, 1218, 669.

Example 21. N-(diphenylmethyl)- 4-methyl-3-oxo-4-AZ the Ali method, similar to that described in example 20, the interaction of N-(diphenylmethyl)- 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide, obtained as described in example 1, with idestam-ethyl.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.68 (3H, singlet), to 0.88 (3H, singlet), of 1.05 (3H, triplet, J 8 Hz), 0,60 - 2,50 (20N, multiplet), is 3.08 (1H, doublet of doublets, J 11 and 2 Hz) at 3.25 (1H, multiplet), 3,74 (1H, multiplet), 5,88 (1H, doublet, J 8 Hz), 6,28 (1H, doublet, J 8 Hz), 7,10 7,40 (10H, multiplet).

Range of the infrared absorption (KBr),maxcm-1: 3292, 2936, 1671, 1619, 1530, 1447, 1224, 698.

Example 22. N-(diphenylmethyl)- 4-allyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 47 was obtained by the method similar to that described in example 20, the interaction of N-(diphenylmethyl)- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide, obtained as described in example 1 with methyl-allyl.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.67 (3H, singlet), of 0.90 (3H, singlet), 0,70 2,40 (N, multiplet), 3,11 (1H, doublet of doublets, J 10 and 3 Hz), 3,80 (1H, doublet of doublets, J 16 and 5 Hz), 4,43 (1H, multiplet), to 5.08 (1H, multiplet), 5,12 (1H, multiplet), USD 5.76 (1H, multiplet), by 5.87 (1H, doublet, J 9 Hz), 6,28 (1H, doublet, J 1624, 1531, 1444, 1223, 698.

Example 23. N-(diphenylmethyl)- 4-benzyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

Indicated in the name of example, the target compound with a yield of 55 was obtained by the method similar to that described in example 20, the interaction of N-(diphenylmethyl)- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide, obtained as described in example 1 with methyl-benzyl.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.65 (3H, singlet), of 0.93 (3H, singlet), 0,70 2,30 (N, multiplet), 2,55 - to 2.65 (2H, multiplet), 3,10 (1H, doublet of doublets, J 11 and 3 Hz), 4,45 (doublet, J 16 Hz), to 5.03 (1H, doublet, J 16 Hz), to 5.85 (1H, doublet, J 9 Hz), 6,27 (1H, doublet, J 9 Hz), 7,10 7,40 (15 NM, multiplet).

Absorption spectrum in the infrared region (KBr)maxcm-1: 3310, 3027, 2941, 1643, 1519, 1494, 1451, 1409, 1304, 1226, 699.

Example 24. N-(diphenylmethyl)- 4-methyl-3-oxo-4-Aza-5-alpha-androst-17-beta-carboxamide.

Target connection specified in the title of the example, with the release of 83 was obtained similar to that described in example 1 way, interacting 4-methyl-3-oxo-4-Aza-5-alpha-androst-17-beta-carboxylic acid, obtained according to the example of obtaining the source material 4, with diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3), del is 5,86 (1H, doublet, J 8 Hz, 5,88 (1H, doublet, J 8 Hz), 6,28 (1H, doublet, J 8 Hz), to 6.67 (1H, doublet, J 10 Hz), 7,20 7,40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1]: 2966, 2940, 1663, 1602, 1519, 1494, 1448, 1394, 1221, 698.

Example 25. N-(diphenylmethyl)- 4-methyl-3-oxo-4-Aza-androst-5-ene-17--beta-carboxamide.

The connection specified in the title of the example, with the release of 82 was obtained by the method similar to that described in example 1, the interaction of 3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid, obtained as described in example obtaining raw materials 5, diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0,70 (3H, singlet), of 1.05 (3H, singlet), 0,80 2,35 (N, multiplet), 2,45 - to 2.57 (2H, multiplet), of 3.12 (3H, singlet), 5,04 (1H, multiplet), of 5.89 (1H, doublet, J 9 Hz), of 6.29 (1H, doublet, J 9 Hz), 7,10 7,40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3314, 2944, 1669, 1642, 1627, 1524, 1494, 1385, 1124, 1054, 699.

Example 26. N-(1,1-diphenylether)- 4-methyl-3-oxo-4-5-alpha-Aza-androstane-17-beta-carboxamide.

Target connection specified in the title of the example, with the release of 65 was obtained in a manner analogous to the one described in example 2, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carbon of the Sabbath.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0,70 (3H, singlet), of 0.90 (3H, singlet), 0,70 2,30 (3H, multiplet, of 2.20 (3H, multiplet), 2,48 (2H, multiplet), to 2.94 (3H, singlet), totaling 3.04 (1H, doublet of doublets, J 13 and 4 Hz), 5,97 (1H, broad), 7,20 7,40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2940, 2872, 1681, 1643, 1492, 1446, 1392, 1228, 762, 699.

Example 27. N-(1,1-diphenylether)- 4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

Target connection specified in the title of the example, with the release of 44 was obtained in a manner analogous to the one described in example 2, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid obtained by example of the initial preparation of compounds 4 with 1,1-diphenylethylene.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0,70 (3H, singlet), of 0.93 (3H, singlet), 0,90 2,30 (N, multiplet), of 2.20 (3H, singlet), 2,96 (3H, singlet), to 3.35 (1H, doublet of doublets, J 13 and 4 Hz), 5,90 (1H, doublet, J 10 Hz), 5,98 (1H, broad), 6,69 (1H, doublet, J 10 Hz), 7,20 7,40 (10 H, multiplet).

Absorption spectrum in the infrared region (KBr), maxcm-1: 2940, 1663, 1604, 1492, 1446, 699.

Example 28. N-(1,1-diphenylether) -4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

Connection science 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid, obtained as described in example retrieve the source of the compounds 5, 1,1-diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million d: to 0.73 (3H, singlet), of 1.06 (3H, singlet), 1,00 2,35 (N, multiplet), of 2.20 (3H, singlet), of 3.13 (3H, singlet), 5,04 (1H, multiplet), 5,96 (1H, broad), 7,20 7,40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr) maxcm-1: 2966, 2943, 1641, 1492, 1447, 1388, 1324, 1241, 699.

Example 29. N-(1,2-diphenylether)- 4-methyl-3-oxo-4-Aza-5-alpha-androst-17-beta-carboxamide.

The connection specified in the title of the example, with a yield of 75 was obtained in a manner analogous to the one described in example 1, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androst-17-beta-carboxylic acid, obtained as described in the example of a parent compounds 2, 1,2-diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days between 0.46 and 0.50 (all 3H, each singlet), 0,85 and 0,86 (all 3H, each singlet), 0,60 2,50 (20N, multiplet), only 2.91 (3H, singlet), 2,85 3,20 (3H, multiplet), 5,26 and 5,33 (all 1H, each doublet of doublets, J 8 and 7 Hz), 5,47 and 5,57 (all 1H, each doublet, J 8 Hz), 7,00 7,40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3314, 2937, 2870, 1644, 1529, 1453, 1393, 1305, 1229, 699.

An example is s, indicated in the name of example, with the release of 78 was obtained in a manner analogous to the one described in example 1, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androst-17-beta-carboxylic acid, obtained as described in example obtaining raw materials 4, 1,2-diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0,48 0,52 (all 3H, each singlet), 0,90 and 0,91 (all 3H, each singlet), 0,80 - 2,20 (N, multiplet), 2,95 (3H, singlet), 2,90 3,24 (2H, multiplet), to 3.33 (1H, doublet, J 13 Hz), 5,27 and 5,34 (all 1H, each doublet of doublets, J 8 and 7 Hz), 5,48, and 5.58 (all 1H, each doublet, J 8 Hz), by 5.87 and of 5.89 (all 1H, each doublet, J 10 Hz), 6,67 and 6,69 (all 1H, each doublet, J 10 Hz), 7,00-7,40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3320, 2939, 1659, 1602, 1526, 699.

Example 31. N-(1,2-diphenylether)- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 78 was obtained in a manner analogous to the one described in example 1, the interaction of 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid, obtained as described in example retrieve the source of the compounds 5, 1,2-diphenylethylamine.

Spectrum of nuclear magnetic resonance (DCl3Delta, million days of 0.49 and 0.53 per share (all 02 (1H, multiplet), 5,27 and 5,34 (all 1H, each doublet of doublets, J 8 and 7 Hz), 5,50 and 5,59 (all 1H, each doublet, J 8 Hz), 7,00 - 7,38 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2944, 2871, 1669, 1642, 1524, 1495, 1453, 1387, 1243, 699.

Example 32. N-/(S)- 1,2-diphenylether-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 96 was obtained by the method similar to that described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid with (S)-1,2-diphenylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.50 (3H, singlet), of 0.87 (3H, singlet), 0,70 3,20 (N, multiplet in), 5.25 (1H, Quartet, J 5 Hz), vs. 5.47 (1H, broad), to 5.58 (1H, doublet, J 5 Hz), 7,00 7,40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2938, 2872, 1663, 1497, 1453, 1360, 1308, 1230, 699.

Example 33. N-/(R)-1,2-diphenylether/- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 83 was obtained by the method similar to that described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid with (R)-1,2-diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, mee), 7,10-7,40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3218, 2935, 1663, 1494, 1453, 1361, 1305, 1229, 1121, 704.

Example 34. N,N-dibenzyl-4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of example, with yields of 80 was obtained by the method similar to that described in example 1, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid, obtained as described in the example of a parent compounds 2, with N,N-diphenylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0,89 (6N, singlet), 0,65 2,50 (N, multiplet), a 2.75 (1H, triplet, J 10 Hz), of 2.72 (3H, singlet), of 3.00 (1H, doublet of doublets, J 13 and 14 Hz in), 3.75 (1H, doublet, J 15 Hz), 4,15 (1H, doublet, J 16 Hz), 4,91 (1H, doublet, J 16 Hz), 6,46 (1H, doublet, J 15 Hz), 7,07 7,40 (10H, multiplet),

Absorption spectrum in the infrared region (KBr),maxcm-1: 2941, 2872, 1642, 1494, 1451, 1471, 1389, 1305, 1215, 735, 700.

Example 35. N,N-dibenzyl-4-methyl-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of example, with 68 output was obtained in a manner analogous to the one described in example 1, the interaction of 4-methyl-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid, obtained as described in the example is 3Delta, million days of 0.90 (3H, singlet), were 0.94 (3H, singlet), 0,80 2,20 (15 NM, triplet), a 2.75 (1H, doublet, J 9 Hz), 2,95 (3H, singlet), and 3.31 (1H, doublet of doublets, J 12 and 4 Hz in), 3.75 (1H, doublet, J 13 Hz), 4,18 (1H, doublet, J 15 Hz), 4,19 (1H, doublet, J 15 Hz), the 5.45 (1H, doublet, J 13 Hz), of 5.82 (1H, doublet, J 10 Hz), only 6.64 (1H, doublet, J 10 Hz), 7,06 7,73 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2940, 1664, 1641, 1606, 1494, 1424, 1217, 820, 735, 698.

Example 36. N,N-dibenzyl-4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the output 74 received in a manner analogous to the one described in example 1, the interaction of 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid, obtained as described in example retrieve the source of the compounds 5, N,N-dibenzylamino.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.92 (3H, singlet), of 1.06 (3H, singlet), 1,00 2,60 (17H, multiplet), 2,77 (1H, triplet, J 9 Hz), 3,11 (3H, singlet), of 3.75 (1H, doublet, J 13 Hz), 4,18 (1H, doublet, J 15 Hz), 4,94 (1H, doublet, J 15 Hz), to 5.03 (1H, multiplet), vs. 5.47 (1H, doublet, J 13 Hz), 7,07 the 7.43 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 296, 2902, 1666, 1641, 1411, 1201, 1054, 732, 697.

Example 37. N-(1-methyl-1-phenylethyl)- 3-oxo-4-Aza-5-alpha-androstane-17-beta-CA,2-piperidinomethyl in this order were added to 30 ml of dry toluene. Then the reaction solution was left overnight at room temperature with stirring, after which it was purified column chromatography through 100 g of silica gel. Gradient elution with a mixture of acetone methylene chloride in ratios from 1 9 to 1 1 by volume received 5,96 g of 2-peridotite 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid.

150 mg of 2-peridotite obtained as described above and 500 mg of 1-methyl-1-phenethylamine in this order were added to 5 ml of dry tetrahydrofuran. Then the reaction solution was left at room temperature for three days under stirring. After this time the solution was diluted with 100 ml of methylene chloride, washed with 1 N. aqueous hydrochloric acid, water, aqueous solution of acid sodium carbonate and saturated aqueous solution of sodium chloride in the order listed and dried over anhydrous magnesium sulfate. The solvent is then drove away under reduced pressure. The obtained residue was purified column chromatography through 15 g of silica gel. Gradient elution with a mixture of acetone methylene chloride in ratios from 1 9 to 1: 1 by volume received 112 mg of target compound indicated in the title of the example.

Range nuclear meth), 1,72 (3H, singlet), 2,35 2,50 (2H, multiplet), 3,06 (1H, doublet of doublets, J 12 and 5 Hz), 5,52 (1H, broad band), the ceiling of 5.60 (1H, broad band), 7,20 was 7.45 (5H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2938, 2919, 1699, 1672, 1495, 1447, 1361, 1308, 1257, 1233, 697.

Example 38. N-(1-methyl-1-phenylethyl)- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

Indicated in the name of example, the connection with the release of 70 was obtained in a manner analogous to the one described in example 37, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid and 1-methyl-1-phenethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days is 0.69 (3H, singlet), and 0.98 (3H, singlet), from 0.90 to 2.25 (M, multiplet), 1,71 (3H, singlet), at 1.73 (3H, singlet), to 3.33 (1H, triplet, J 8 Hz), of 5.53 (1H, broad band), 5,69 (1H, broad band), of 5.84 (1H, doublet, J 10 Hz), for 6.81 (1H, doublet, J 10 Hz), 7,20 was 7.45 (5H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2969, 2937, 1672, 1598, 1494, 1446, 1254, 821, 761, 696.

Example 39. N-(1-methyl-1-phenylethyl)-5-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

Indicated in the name of example, the connection to the output 68 received in a manner analogous to the one described in example 37, the interaction of 3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic it is. ,71 (3H, singlet), is 1.11 (3H, singlet), 1,00 2,60 (N, multiplet), 1,71 (3H, singlet), at 1.73 (3H, singlet), a 4.83 (1H, multiplet), 5,52 (1H, broad band), 7,20-7,50 (6N, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2969, 2940, 1707, 1673, 1495, 1448, 1386, 1225, 671, 697.

Example 40. N-(1-methyl-1-phenylethyl)- 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

Indicated in the name of example, the connection to the output 82 received in a manner analogous to the one described in example 37, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid, obtained as described in the example of a parent compounds 2, with 1-methyl-1-phenylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days is 0.69 (3H, singlet), to 0.89 (3H, singlet), 0,70 2,20 (N, multiplet), to 1.70 (3H, singlet), at 1.73 (3H, singlet), 2,47 (2H, multiplet), to 2.94 (3H, singlet), totaling 3.04 (1H, doublet of doublets, J 12 and 3 Hz), of 5.53 (broad), 7,20 is 7.50 (5H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 335, 2967, 2942, 1670, 1628, 1547, 1527, 1442, 1368, 1228, 762, 698.

Example 41. N-(1-methyl-1-phenylethyl)- 4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

Indicated in the name of example, the connection to the output 66 is received in a manner analogous to opisanych described in the example of a parent compounds 4, 1-methyl-1-phenethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days is 0.69 (3H, singlet), of 0.93 (3H, singlet), 0,90 2,35 (N, multiplet), 1,71 (3H, singlet), at 1.73 (3H, singlet), 2,96 (3H, singlet), to 3.35 (1H, doublet of doublets, J 13 and 4 Hz), of 5.53 (1H, broad), of 5.85 (1H, doublet, J 10 Hz), of 6.68 (1H, doublet, J 10 Hz), 7,20 was 7.45 (5H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3332, 2964, 2943, 1674, 1658, 1604, 1537, 1448, 1244, 821, 705.

Example 42. N-(1-methyl-1-phenylethyl)- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

Indicated in the name of example, the connection with the release of 70 was obtained in a manner analogous to the one described in example 37, the interaction of 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid, obtained as described in the example of a parent compound 5, with 1-methyl-1-phenethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.71 (3H, singlet), of 1.06 (3H, singlet), 1,00 2,30 (N, multiplet), 1,71 (3H, singlet), of 1.74 (3H, singlet), 2,50 2,60 (2H, multiplet), of 3.13 (3H, singlet), 5,04 (1H, multiplet), of 5.53 (1H, broad), 7,20 was 7.45 (5H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3333, 3970, 1636, 2950, 1677, 1519, 1448, 1382, 1245, 761, 696.

Example 43. N-/1-(4-methoxyphenyl)-1-mutilate the Odom 82 received by way similar to that described in example 37, the interaction of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid with 1-(4-methoxyphenyl)-1-methylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.68 (3H, singlet), 0,9, (3H, singlet), 0,70 2,80 (20N, multiplet), was 1.69 (3H, singlet), 1,71 (3H, singlet), is 3.08 (1H, doublet of doublets, J 13 and 4 Hz), of 3.80 (3H, singlet), 5,49 (1H, broad), and 6.25 (1H, broad), to 6.88 (2H, doublet, J 9 Hz), 7,30 (2H, doublet, J 9 Hz).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2939, 1701, 1674, 1615, 1614, 1497, 145, 1360, 1251, 1180, 1034, 827.

Example 44. N-1/-(4-methoxyphenyl)-1-methylethyl/- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 78 was obtained in a manner analogous to the one described in example 37, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid with 1-(4-methoxyphenyl)-1-methylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.68 (3H, singlet), and 0.98 (3H, singlet), 0,90 2,20 (NN, multiplet), to 1.70 (3H, singlet), at 1.73 (3H, singlet), to 3.35 (1H, doublet, J 9 Hz), of 3.80 (3H, singlet), of 5.48 (1H, broad), USD 5.76 (1H, broad), of 5.83 (1H, doublet, J 10 Hz), PC 6.82 (1H, doublet, J 10 Hz), to 6.88 (1H, doublet, J 9 Hz), 7,32 (2H, doublet, J 9 Hz).

Absorption spectrum in Imereti/- 3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 65 was obtained by the method similar to that described in example 37, the interaction of 3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid with 1-(4-methoxyphenyl)-1-methylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0,70 (3H, singlet), 1,10 (3H, singlet), 1,00 2,70 (N, multiplet), to 1.70 (3H, singlet), 1,72 (3H, singlet), of 3.80 (3H, singlet), 4,91 (1H, multiplet), of 5.50 (1H, broad, to 6.88 (2H, doublet, J 9 Hz), 7,34 (2H, doublet, J 9 Hz), 7,95 (1H, broad).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2940, 1708, 1672, 1615, 1514, 1497, 1385, 1251, 1180, 1033, 825.

Example 46. N-/1-(4-methoxyphenyl)-1-methylethyl/- 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 82 was obtained by the method similar to that described in example 37, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid, obtained in example obtain the starting compound 2 with 1-(4-methoxyphenyl)-1-methylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.68 (3H, singlet), of 0.90 (3H, singlet), 0,70 2,60 (20N, multiplet), was 1.69 (3H, multiplet), 1,71 (3H. singlet), to 2.94 (3H, singlet), 3,05 (1H doublet of doublets, J 13 and 4 Hz), of 3.78 (3H, si is B>maxcm-1: 3333, 2940, 1675, 1643, 1513, 1455, 1384, 1304, 1247, 1180, 1035, 828.

Example 47. N-/1-(4-methoxyphenyl)-1-methylethyl/- 4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

Indicated in the name of example, the connection to the output 71 received in a manner analogous to the one described in example 37, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid, obtained in example 4 to obtain the original compounds, 1-(4-methoxyphenyl)-1-methylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days is 0.69 (3H, singlet), to 0.92 (3H, singlet), 0,80 2,30 (N, multiplet), to 1.70 (3H, singlet), 1,72 (3H, singlet), 2,96 (3H, singlet), to 3.36 (1H, doublet of doublets, J 13 and 4 Hz), with 3.79 (3H, singlet), of 5.50 (1H, broad), 5,86 (1H, doublet, J 10 Hz, 6,69 (1H, doublet, J 10 Hz), to 6.88 (1H, doublet, J 9 Hz), 7,35 (1H, doublet, J 9 Hz).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2968, 2940, 1662, 1513, 1453, 1247, 1180, 1034, 827.

Example 48. N-/1-(4-methoxyphenyl)-1-methylethyl/- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

Target connection specified in the title of the example, with the release of 72 was obtained in a manner analogous to the one described in example 37, the interaction of 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid, obtained when the aqueous resonance (CDCl3Delta, million D. 0,70 (3H, singlet), of 1.06 (3H, singlet), 1,00 2,30 (N, multiplet), 2,50 - 2,60 (2H, multiplet), to 1.70 (3H, singlet) 1,72 (3H, singlet), of 3.12 (3H, singlet), of 3.80 (3H, singlet), 5,04 (1H, multiplet), of 5.50 (1H, broad), to 6.88 (2H, doublet, J 9 Hz), 7,32 (1H, doublet, J 9 Hz).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3344, 2967, 294, 1670, 1642, 1513, 1455, 1386, 1305, 1247, 1180, 1034, 829.

Example 49. N-/1-(2-thienyl)-1-methylethyl/- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 96 was obtained by the method similar to that described in example 37, the interaction of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid with 1-(2-thienyl)-1-methylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.67 (3H, singlet), of 0.90 (3H, singlet), is 1.81 (3H, singlet), is 1.82 (3H, singlet), 0,70 2,35 (N, multiplet), 2,39 of 2.45 (2H, multiplet), 3,06 (1H, doublet of doublets, J 11 and 4 Hz), the 5.51 (1H, broad), 5,78 (1H, broad), 6,91 of 6.99 (2H, multiplet), 7,17 (1H, doublet of doublets, J 5 and 2 Hz).

Absorption spectrum in the infrared region (KBr), maxcm-1: 3296, 2937, 1663, 1449, 1360, 695.

Example 50. N-/1-(2-thienyl)-1-methylethyl/- 3-oxo-4-Aza-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the output 27 of polossaty with 1-(2-thienyl)-1-methylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3million days of 0.71 (3H, singlet), 1,10 (3H, singlet), 1,05 2,30 (N, multiplet), is 1.82 (3H, singlet), 1,89 (3H, singlet), 2,47 of 2.53 (2H, multiplet), is 4.85 (1H, doublet, J 3 Hz), 5,54 (1H, singlet), 6,91 of 6.99 (2H, multiplet), 7,17 (1H, doublet of doublets, J 5 and 2 Hz), 7,53 (1H, broad).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3200, 2940, 1706, 1678, 1495, 1386, 1246, 1225, 695.

Example 51. N/alpha-(4-chlorophenyl)-benzyl/- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example, with the output 84 received in a manner analogous to the one described in example 2, the interaction of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid and alpha-(4-chlorophenyl)-benzylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.66 and 0.67 (all 3H, each singlet), of 0.89 and 0.90 (all 3H, each singlet), 0,73 2,45 (20 H, multiplet), was 3.05 (1H, doublet of doublets, J 11 and 4 Hz), of 5.84 (1H, doublet, J 8 Hz), 5,88 (1H, broad), 6.22 per and 6.25 (all 1 N, each doublet, J 8 Hz), 7,13 7,37 (N, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3360, 2978, 1736, 1652, 1514, 1371, 1199.

Example 52. N-/-alpha-(4-chlorophenyl)-benzyl/- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The target connection, the decree-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid and alpha-(4-chlorophenyl)-benzylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.68 and 0.69 (all 3H, each singlet), of 0.96 and 0.97 (all 3H, each singlet), 0,80-2,30 (N, multiplet), to 3.33 (1H, triplet, J 8 Hz), of 5.68 (1H, broad), 5,80 of 5.85 (2H, multiplet), 6,34 and 6.26 (all 1H, each doublet, J 10 Hz), 6,79 and 6,82 (all 1H, each doublet, J 10 Hz), 7,14 7,37 (N, multiplet).

Absorption spectrum in the infrared region (KBr), maxcm-1: 3293, 2936, 1676, 1601, 1490, 815, 700.

Example 53. N/alpha-(4-chlorophenyl)-benzyl/- 3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

Target connection specified in the title of the example, with the release of 78 was obtained in a manner analogous to the one described in example 2, by interacting 3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid alpha-(4-chlorophenyl)-benzylamino.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days to 0.70 and 0.71 (all 3H, each singlet), 1.00 and 1.10 for (all 3H, each singlet), 1,10 2,60 (N, multiplet), 4,89 4,91 (1H, multiplet), 5,86 (1H, doublet, J 7 Hz), 6,23 and 6.26 (all 1H, each doublet, J 7 Hz), 7,15-7,38 (M, multiplet), 7,87 (wide band).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2943, 1661, 1490, 1386, 694.

Example 54. N/alpha-(4-chlorophenyl)-benzyl-/- 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

Joint-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid, obtained according to the example of obtaining the source compounds 2, alpha-(2-chlorophenyl)-benzylamino.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.66 and 0.67 (all 3H, each singlet), of 0.87 and 0.88 (all 3H, each singlet), 0,70 2,60 (20N, multiplet), to 2.94 (3H, singlet), 3,01 of 3.07 (1H, multiplet), of 5.83 (1H, doublet, J 6 Hz), 6,22 of 6.26 (1H, multiplet), 7,14 - 7,37 (N, multiplet).

Absorption spectrum in the infrared region (KBr), maxcm-1: 3305, 2940, 1646, 1622, 1521, 1490, 1226, 700.

Example 55. N/alpha-(4-chlorophenyl)-benzyl/- 4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 58 was obtained by the method similar to that described in example 2, the interaction of 4-methyl-4-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid, obtained as described in the example of a parent compounds 4, c alpha-(4-chlorophenyl)-4-benzylamino.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.67 and 0.68 (all 3H, each singlet), of 0.91 and 0.92 (all 3H, each singlet), 0,84-2,30 (N, multiplet), to 2.94 (3H, singlet), to 3.34 (1H, doublet doublet, J 13 and 3 Hz), of 5.82 by 5.87 (2H, multiplet), 6,23 and 6.26 (all 1H, each doublet, J 8 Hz), 6,74 and 6,77 (all 1H, each doublet, J 10 Hz), 7,14 of 7.64 (M, multiplet).

Range of pogloshena is a-(4-chlorophenyl)-benzyl/- 4-methyl-3-oxo-4-Aza-androstane-5-ene-17-beta-carboxamide.

The connection specified in the title of example, with yields of 80 was obtained by the method similar to that described in example 2, the interaction of 4-methyl-3-oxo-4-Aza-androstane-5-ene-17-beta-carboxylic acid, obtained in example retrieve the source of the compounds 5, c alpha-(4-chlorophenyl)-benzylamino.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days to 0.69 and 0.70 (all 3H, each singlet), the 1.04 and 1.05 (all 3H, each singlet), 1,10 2,60 (N, multiplet), of 3.12 (3H, singlet), 5,02 of 5.05 (1H, multiplet), to 5.85 (1H, doublet, J 7 Hz), 6,23 and 6.26 (all 1H, each doublet, J 7 Hz), 7,15 7,38 (M, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3316, 2945, 1670, 1644, 1518, 1490, 1388, 700.

Example 57. N/alpha(4 oksifenil)-benzyl/- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 63 was obtained in a manner analogous to the one described in example 37, the interaction of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid and alpha-(4-chlorophenyl)-4-benzylamino.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.66 (3H, singlet), to 0.88 (3H, singlet), 0,70 3,02 (N, multiplet), was 3.05 (1H, doublet of doublets, J 12 and 4 Hz), 5,85 of 5.89 (2H, multiplet), to 6.19 (1H, doublet, J 8 Hz), 6,72 of 6.78 (2H, multiplet), 7,01 7,06 (2H, m is 1495, 1228, 699.

Example 58. N-/-alpha-(4 oksifenil)-benzyl/- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of example, with access 95 was obtained by the method similar to that described in example 37, the interaction of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid with alpha-(4-hydrofoil)-benzylamino.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.67 and 0.68 (all 3H, each singlet), of 0.95 and 0.96 (all 3H, each singlet), 0,80 3,20 (17H, multiplet), 3,32 (1H, triplet, J 8 Hz), 5,52 (1H, broad), of 5.82 (1H, doublet, J 10 Hz), 5,90 (1H, doublet, J 7 Hz), to 6.19 (1H, doublet, J 7 Hz), 6,72 for 6.81 (3H, multiplet), 7,02-7,07 (2H, multiplet), 7,20-to 7.35 (5H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3292, 2937, 1668, 1613, 1596, 1514, 1495, 1450, 1223, 816, 699.

Example 59. N/alpha(oxyphenyl)-benzyl/- 3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

The target compound is indicated in the name of example, with an output of 77 was obtained by the method similar to that described in example 37, the interaction of 3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid with alpha-(4 oksifenil)-benzylamino.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.65 and 0.69 (all 3H, each singlet), 0,99 and 1.08 (all 3H, cadet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3189, 2943, 1673, 1661, 1612, 1514, 1493, 1386, 1222, 832, 700.

Example 60. N/alpha(4 oksifenil)-benzyl/- 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 46 was obtained in a manner analogous to the one described in example 2, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid, obtained as described in the example of a parent compounds 2, alpha-(4 oksifenil)-benzylamino.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.67 (3H, singlet), of 0.87 and 0.88 (all 3H, each singlet), 0,70 2,50 (N, multiplet), of 2.92 (3H, singlet), 3,03 (1H doublet of doublets, J 13 and 3 Hz), of 5.84 by 5.87 (1H, multiplet), 6,17 6,21 (1H, multiplet), 6,74 6,79 (2H, multiplet), 7,02 7,06 (2H, multiplet), then 7.20 to 7.35 (5H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3292, 2940, 1644, 1671, 1590, 1514, 1494, 1452, 1228, 699.

Example 61. N-/(R)-2-(4-were)-1-phenylethyl/ -3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of example, with yields of 80 was obtained by the method similar to that described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid with (R)-2-(4-meth singlet), to 0.88 (3H, singlet), of 2.25 (3H, singlet), 0,65 3,30 (N, multiplet), of 5.34 (1H, Quartet, J 5 Hz), of 5.48 (1H, doublet, J 5 Hz), to 6.80 (1H, broad), 7,1 7,4 (N, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3218, 2935, 1664, 1495, 1305, 1121.

Example 62. N-/(S)-2-(4-were)-1-phenylethyl/- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example, exit 81 was obtained in a manner analogous to the one described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid with (S)-2-(4-were)-1-phenethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.51 (3H, singlet), to 0.88 (3H, singlet), 0,70 3,20 (N, multiplet), to 2.29 (3H, singlet), 5,23 (1H, Quartet, J 7 Hz), to 5.57 (1H, doublet, J 7 Hz), 6,50 (1H, broad), 6,94 (2H, doublet, J 8 Hz), 7,02 (2H, doublet, J 8 Hz), to 7.15 to 7.35 (5H, multiplet).

Absorption spectrum in the infrared region (KBr), maxcm-1: 2939, 1664, 1516, 1496, 1371, 1361, 1313, 1234, 1120, 789, 704.

Example 63. N-/(S)-2-(4-were)-1-phenylethyl/- 4-methyl--3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the name of the example, with the release of 46 was obtained in a manner analogous to the one described in example 2, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-cartilagineum.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.51 (3H, singlet) to 0.85 (3H, singlet), 0,70 2,50 (20N, multiplet), 2029 (3H, singlet), only 2.91 (3H, singlet), 2,90 of 3.15 (3H, multiplet), a 5.25 (1H, Quartet, J 7 Hz), to 5.58 (1H, doublet, J 7 Hz), to 6.95 (2H, doublet, J 8 Hz), 7,02 (2H, doublet, J 8 Hz), to 7.15 to 7.35 (5H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3323, 2942, 1646, 1516, 1454, 1393, 1305, 1228, 1103, 1037, 700.

Example 64. N, N-diphenyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carbohydrazide.

The connection specified in the title of example, with exit 57 was obtained in a manner analogous to the one described in example 37, by interacting with 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid with N,N-diphenylhydrazine.

Spectrum of nuclear magnetic resonance (CDCl3million days to 0.70 (3H, singlet), of 0.90 (3H, singlet), 0,70 2,50 (20N, multiplet), was 3.05 (1H, doublet of doublets, J 13 and 4 Hz), the 5.45 (1H, broad), 6,97-7.37 (10H, multiplet), 7,51 (1H, broad band).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3198, 2934, 1698, 1652, 1589, 1491, 1324, 1188, 1120, 746, 693.

Example 65. N,N-diphenyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carbohydrazide.

The connection specified in the title of the example, with the release of 22 was obtained in a manner analogous to the one described in example 2, ot the KTR nuclear magnetic resonance (CDCl3Delta, million days of 0.71 (3H, singlet), of 0.97 (3H, singlet), 0,86 of 2.25 (20N, multiplet), to 3.33 (1H, doublet of doublets, J 9 and 7 Hz), of 5.48 (1H, broad), of 5.82 (1H, doublet, J 10 Hz), 6,79 (1H, doublet, J 9 Hz), 6,98 to 7.35 (10H, multiplet), 7,53 (1H, singlet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3211, 2931, 1701, 16668, 1589, 1494, 1330, 814, 747, 693.

Example 66. N,N-diphenyl-3-oxo-4-Aza-androst-5-ene-17-beta-carbohydrazide.

The connection specified in the title of the example, with the release of 25 was obtained in a manner analogous to the one described in example 2, the interaction of 3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid with N,N-diphenylhydrazine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days to 0.73 (3H, singlet), 1,10 (3H, singlet), 0,88 of 2.51 (M, multiplet), 4,78 (1H, multiplet), 6,98 7,31 (10H, multiplet), 7,51 (1H, singlet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 4320, 2944, 1682, 1662, 1590, 1495, 1385, 1222, 748, 691.

Example 67. N,N-diphenyl-4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carbohydrazide.

The connection specified in the title of the example, with the release of 35 was obtained in a manner analogous to the one described in example 2, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid and N,N-diphenylhydrazine.

Range of the poison is 3H, singlet), 3,06 (1H, doublet of doublets, J 12 and 3 Hz) 6,98 7,34 (10H, multiplet), to 7.50 (1H, singlet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3236, 3208, 2935, 1695, 1619, 1602, 1494, 754, 693.

Example 68. N,N-diphenyl-4-methyl-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carbohydrazide.

The connection specified in the title of the example, with the release of 44 was obtained in a manner analogous to the one described in example 2, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid and N,N-diphenylhydrazine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.71 (3H, singlet), to 0.92 (3H, singlet), 0,75-2,29 (N, multiplet), 2,95 (3H, singlet), to 3.34 (1H, doublet of doublets, J 13 and 4 Hz), to 5.85 (1H, doublet, J 10 Hz), 6.67 (1H, doublet, J 10 Hz), 6,98 to 7.35 (10H, multiplet), to 7.50 (1H, singlet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3252, 2941, 1664, 1590, 1495, 747, 691.

Example 69. N,N-diphenyl-4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carbohydrazide.

The connection specified in the title of the example, with the release of 25 was obtained in a manner analogous to the one described in example 2, the interaction of 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid, obtained in example retrieve the source of the compounds 5, N,N-diphenylhydrazine.

tiplet), of 2.51 is 2.55 (2H, multiplet), of 3.12 (3H, singlet), 5,02 of 5.05 (1H, multiplet), 6,99 to 7.32 (10H, multiplet), 7,49 (1H, singlet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3246, 2964, 1698, 1622, 1591, 1495, 1332, 754, 694.

Example 70. N-/(1S, 2R)-2-Hydroxy-1,2-diphenylether/- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 60 was obtained in a manner analogous to the one described in example 37, the interaction of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid (1R, 2S)-2-amino-1,2-diphenylethanol.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.60 (3H, singlet), to 0.89 (3H, singlet), 0,70 2,50 (N, multiplet), was 3.05 (1H, doublet of doublets, J 13 and 4 Hz), 5,00 (1H, doublet, J 5 Hz), 5,28 (1H, doublet, J 5 Hz), 7,00-7,30 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3426, 2938, 1659, 1494, 1458, 1387, 1307, 701.

Example 71. N-/(1S, 2R)-2-hydroxy-1,2-diphenylether/- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 88 was obtained by the method similar to that described in example 37, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid (1R,2S)-2-amino-1,2-diphenylethanol.

Spectrum of nuclear magnetic R is Oki), of 3.23 (1H, doublet of doublets, J 13 and 4 Hz), 5,0 (1H, doublet, J 5 Hz), 5,28 (1H, doublet, J 5 Hz), of 5.83 (1H, doublet, J 9 Hz), 6.87 in (1H, doublet, J 9 Hz), 7,05 7,30 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3273, 2933, 1664, 1598, 1496, 1455, 822, 700.

Example 72. N-/(1R, 2S)-2-hydroxy-1,2-diphenylether/- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example, with the output 56 received in a manner analogous to the one described in example 37, the interaction of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid with (1S,2R)-2-amino-1,2-diphenylethanol).

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.66 (3H, singlet), of 0.87 (3H, singlet), 0,70 2,70 (N, multiplet), was 3.05 (1H, doublet of doublets, J 13 and 3 Hz), 5,07 (1H, doublet, J 4 Hz), and 5.30 (1H, doublet of doublets, J 7 and 4 Hz), USD 5.76 (1H, broad), 6,12 (1H, doublet, J 7 Hz), of 6.96-was 7.08 (4H, multiplet), 7,16 7,30 (6N, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-13292, 3210, 2932, 1664, 1490, 1360, 1308, 698, 586.

Example 73. N-/(1R,2S)-2-hydroxy-1,2-diphenylether/- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 71 was obtained by the method similar to that described in example 37, the interaction of 3-oxo-4-Aza-5-alpha-Andro is the mission (CDCl3Delta, million days of 0.57 (3H, singlet), of 0.95 (3H, singlet), 0,80 2,80 (17H, multiplet), to 3.35 (1H, multiplet), to 5.08 (1H, doublet, J 4 Hz), 5,31 (1H, doublet of doublets, J 7 and 4 Hz), of 5.84 (1H, doublet, J 9 Hz), equal to 6.05 (1H, broad), 6,16 (1H, doublet, J 7 Hz), at 6.84 (1H, doublet, J 9 Hz), 6,95 7,40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3438, 3278, 2931, 2846, 1679, 1601, 1494, 1452, 1386, 1220, 1124, 1064, 825, 700, 589.

Example 74. N-(alpha-methoxycarbonyl--alpha phenylbenzyl)- 3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 29 was obtained in a manner analogous to the one described in example 2, the interaction of 3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid and methyl ester diphenylglycine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 1.08 (3H, singlet), of 0.59 (3H, singlet), 1,0 2,55 (N, multiplet in), 3.75 (3H, singlet), 4,80 (1H, multiplet), of 6.99 (1H, broad band), 7,20 to 7.4 (11N, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2966, 2947, 1745, 1681, 1491, 1449, 1242, 1221, 698.

Example 75. N-(diphenylmethyl)- N-methyl-4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with an output of 55 was obtained in a manner analogous to described the frame as described in example 24, with idestam the stands.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days from 0.84 (3H, singlet), 0,8 2,45 (N, multiplet), 2,85 (3H, singlet), of 2.97 (3H, singlet), to 3.35 (1H, doublet of doublets, J 13 and 4 Hz), to 5.58 (1H, doublet, J 10 Hz), of 6.65 (1H, doublet, J 10 Hz), 7,10 to 7.32 (11N, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2934, 1662, 1639, 1606, 1446, 1396, 1272, 1103, 700.

Example 76. N-(diphenylmethyl)-4-(2-carboxyethyl)- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

250 mg of N-(diphenylmethyl)-4-(3-oksipropil)- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide, obtained as described below in example 77 was dissolved in 10 ml of acetone and added to a solution of 1 ml of Jones reagent at 0oC. Then the reaction mixture was stirred at 0oC for 30 min, and then to the mixture was added isopropyl alcohol. Insoluble material was filtered using a celite (trade mark) as the accelerator was filtered and the filtrate are condensed by evaporation under reduced pressure. The crystals which precipitated were collected, washed with diethyl ether and received 202 mg of the target compound.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.68 (3H, singlet), to 0.88 (3H, singlet), 0,70 2,65 (22N, mult is 10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3301, 2942, 1729, 1643, 1622, 1600, 1494, 1449, 1227, 1193, 1029, 699.

Example 77. N-(diphenylmethyl)-4-(3-oksipropil) -3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

Indicated in the name of the example compound was obtained with the yield of 70 in a manner analogous to the one described in example 1, the interaction of 4-(3-oksipropil)-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid with diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.68 (3H, singlet), of 0.90 (3H, singlet), 0,70 2,30 (20N, multiplet), 2,40-of 2.56 (2H, multiplet), 2,90 (1H, broad), 3,06 (1H, doublet of doublets, J 13 and 4 Hz), 3,40 of 3.78 (4H, multiplet), by 5.87 (1H, doublet, J 8 Hz), 6,30 (1H, doublet, J 8 Hz), 7.18 in-7,40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3309, 2940, 1644, 1618, 1522, 1494, 1448, 1412, 1227, 699.

Example 78. N-(1,2-di-(2-thienyl)-ethyl)- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example was obtained with the yield 59 manner similar to that described in example 1, the reaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid and 1,2-di-(2-thienyl)ethylamine.

Spectrum of nuclear magnetic resonance (CDCl3), del the years of doublets, J 11 and 3 Hz), 6,72 of 7.25 (7H, multiplet).

Absorption spectrum in the infrared region (KBr), maxcm-1: 2993, 1675, 1498, 695.

Example 79. N-/2-(4-forfinal)-1-(2-thienyl)-ethyl/- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 64 was obtained in a manner analogous to the one described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid with 2-(4-forfinal)-1-(2-thienyl)-ethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.51 and 0.61 (all 3H, each singlet), of 0.95 (3H, singlet), is 3.08 of 3.42 (3H, multiplet), 5,35 5,73 (3H, multiplet), of 5.82 (1H, doublet of doublets, J 11 and 3 Hz), 6.73 x of 7.23 (8H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3288, 2934, 1675, 1599, 1509, 1443, 1221, 817, 696.

Example 80. N-/2-(4-were)-1-(2-thienyl)ethyl/- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the header, with the release of 46 was obtained by the method of example 1, the reaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid with 2-(4-were)-1-(2-thienyl)-ethylamine.

Spectrum of nuclear magnetic resonance (DCl3Delta, million days of 0.45 and 0,58 (total 3H, each singlet), of 0.93 (3H, singlet), 2,31 (3H, singlet), 3,p absorption in the infrared region (KBr),maxcm-1: 3288, 2932, 1675, 1599, 1515, 1227, 816, 695.

Example 81. N-/2-(4-methoxyphenyl)-phenylethyl/- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 44 was obtained in a manner analogous to the one described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid with 2-(4-methoxyphenyl)-1-phenethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0.52 and 0.53 per share (all 3H, each singlet), were 0.94 and 0.95 (all 3H, each singlet), 2,91-3,18 (2H, multiplet), and 3.31 (1H, broad singlet), 3,76 (3H, singlet), 5,15 to 5.6 (3H, multiplet), of 5.82 (1H, doublet of doublets, J 11 and 3 Hz), 6,72 - 7,37 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2934, 1675, 1600, 1512, 1248, 1177, 817, 699.

Example 82. N-/-2-(4-methoxyphenyl)-1-(2-thienyl)-ethyl/- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 65 was obtained by the method similar to that described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid and 2-(4-methoxyphenyl)-1-(2-thienyl)-ethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.47 and 0.58, up (all 3H, each singlet), were 0.94 (3H, single of 7.2 (8H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3196, 2931, 1676, 1600, 1513, 1248, 1031, 819.

Example 83. N-/2-(phenyl-1-(2-thienyl)-ethyl/- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 20 was obtained by the method similar to that described in example 20 by the interaction of the N-/2-(phenyl-1-(2-thienyl)-ethyl/- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid and iodotope bromide.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days from 0.4 to 0.60 (all 3H, each singlet), of 1.07 (3H, singlet), with 2.93 (3H, singlet), 3,21 (3H, multiplet), 4,7 5,7 (2H, multiplet), 6,7 7,4 (8H, multiplet).

Absorption spectrum in the infrared region (KBr), maxcm-1: 1666, 1601.

Example 84. N-/2-(phenyl-1-(2-thienyl)-ethyl/- 4-methyl-3-oxo-4-Aza-androst-5-ene-carboxamide.

The connection specified in the title of the example, with the release of 48 was obtained by the method described in example 1, the interaction of 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid, obtained as described in example retrieve the source of the compounds 5, with 2-phenyl-1-(2-thienyl)-ethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.4 and 0.61 (all 3H, each singlet), a 1.08 (3H, singlet),KScm-1: 1665, 1601.

Example 85. N-/2-phenyl-1-(2-thienyl)-ethyl/- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 58 was obtained by the method similar to that described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid and 2-phenyl-1-(2-thienyl)-ethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0.42 and 0.58, up (all 3H, each singlet), of 0.97 (3H, singlet), 3,05 to 3.38 (3H, multiplet), 5,28 (1H, singlet), lower than the 5.37 5,74 (2H, multiplet), 5,80 (1H, doublet of doublets, J 14 and 5 Hz), 6,77 (1H, multiplet), 6,91 (2H, multiplet), 7,08 7,33 (6N, multiplet).

Absorption spectrum in the infrared region (KBr), maxcm-1: 2967, 2933, 1674, 1600, 1469, 1227, 697.

Example 86. N-(Bis-(4-methoxyphenyl)-methyl/- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 69 was obtained in a manner analogous to the one described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid and bis-(4-methoxyphenyl)-methylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.77 (3H, singlet), of 0.97 (3H, singlet), 3,32 (1H, triplet, J 10 Hz), to 3.73 (3H, singlet), with 3.79 (3H, singlet, 5,7 5,9 (3H, SUP>: 2934, 2837, 1678, 1661, 1601, 1509, 1245, 1175, 1034, 818.

Example 87. N-/1,2-di-(2-thienyl)-ethyl/- 3-oxo-4-Aza-5-alpha-androst-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 47 was obtained by the method similar to that described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androst-17-beta-carboxylic acid and 1,2-di-(thienyl)-ethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. and 0,66 0,57 (all 3H, each singlet), and 0.98 (3H, singlet), 3,21 (1H, multiplet), 5,4 5,9 (3H, multiplet), 6,7 7,3 (6N, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 1670, 1601.

Example 88. N-/1,2-di-(2-thienyl)-ethyl/- 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

Indicated in the name of example, the connection to the output 37 was obtained in a manner analogous to the one described in example 1, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid, obtained as described in the example of a parent compounds 2, 1,2-di-(2-thienyl)-ethylamine.

Spectrum of nuclear magnetic resonance (CDCl3: Delta, m D. and 0,66 0,56 (all 3H, each singlet), of 0.97 (3H, singlet), only 2.91 (3H, singlet), of 3.12 (1H, multiplet), 5,4 5,9 (2H, multiplet), 5,7 7,3 (6N, multiplet).

Range of Oct-5-ene-17-beta-carboxamide.

Indicated in the name of example, the connection with the release of 40 was obtained by the method similar to that described in example 1, the interaction of 3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid with 1,2-di-(2-thienyl)-ethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.57 and 0.67 (all 3H, each singlet), and 0.98 (3H, singlet), 5,4 5,9 (4H, multiplet), 6,7 7,3 (6N, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 1665, 1601.

Example 90. N-1,2-di-(2-thienyl)- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 49 was obtained by the method similar to that described in example 1, the interaction of 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid, obtained in example retrieve the source of the compounds 5, 1,2-di-(2-thienyl)-ethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. and 0,66 0,56 (all 3H, each singlet), of 0.97 (3H, singlet), with 2.93 (3H, singlet), 5,4 5,9 (3H, multiplet), 6,7 7,3 (6N, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 1665, 1600.

Example 91. N-/-alpha-(4-methoxyphenyl)-benzyl/- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the on-5-alpha-androst-1-ene-17-beta-carboxylic acid with alpha-(4-methoxyphenyl)-benzylamino.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days is 0.69 (3H, singlet), and 1.00 (3H, singlet), to 3.36 (1H, multiplet), of 3.60 (3H, singlet), 5,73 (1H, broad singlet), of 5.84 (2H, multiplet), 6,23 (1H, doublet, J 8 Hz), 6,78 7,38 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2935, 1678, 1511, 1248, 818, 699.

Example 92. N-/1--alpha-(4-methoxyphenyl)-benzyl/- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 40 was obtained by the method similar to that described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid and alpha-(4-methoxyphenyl)-benzylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.67 (3H, singlet), to 0.89 (3H, singlet), 0,70 2,70 (20N, multiplet), was 3.05 (1H, doublet of doublets, J 11 and 4 Hz), of 5.68 (1H, broad), of 5.83 (1H, doublet, J 7 Hz), to 6.22 (1H, doublet, J 7 Hz), 6,28 to 6.88 (2H, multiplet), 7,10 and 7.36 (7H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3304, 2935, 1664, 1511, 1248, 1033, 700.

Example 93. N-/-alpha-(4-methoxyphenyl)-benzyl/- 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example, with the output 46 received in a manner similar to described the Sano in the example of a parent compounds 2, alpha-(4-methoxyphenyl)-benzylamino.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.67 (3H, singlet), to 0.88 (3H, singlet), 0,70 2,30 (N, multiplet), 2,41 is 2.46 (2H, multiplet), of 2.92 (3H, singlet), to 3.02 (1H, doublet of doublets, J 13 and 3 Hz), with 3.79 (3H, singlet), of 5.83 (1H, doublet, J 8 Hz), to 6.22 (1H, doublet, J 8 Hz), 6,83 6,87 (2H, multiplet), 7,11 to 7.35 (7H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3306, 2936, 1644, 1624, 1511, 1248, 1034, 699.

Example 94. N-/-alpha-(4-methoxyphenyl)-benzyl/- 3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

The connection specified in the title of example, with exit 57 was obtained in a manner analogous to the one described in example 1, the interaction of 3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid and alpha-(4-methoxyphenyl)-benzylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0,70 (3H, singlet), of 1.09 (3H, singlet), 1,05 2,70 (N, multiplet), with 3.79 (3H, singlet), 4,80 4,82 (1H, multiplet), to 5.85 (1H, doublet, J 8 Hz), 6,23 (1H, doublet, J 8 Hz), 6,83 to 6.88 (2H, multiplet), 7,11 7,40 (7H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 1661, 1511, 1249, 1033, 700.

Example 95. N-/-alpha-(4-methoxyphenyl)-benzyl/- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

The target issue for lighting the Sabbath., Samadashvili 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid, obtained as described in example retrieve the source of the compounds 5, alpha-(4-methoxyphenyl)-benzylamino.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0,70 (3H, singlet), was 1.04 (3H, singlet), 1,10 2,30 (N, multiplet), 2,49 - of 2.54 (2H, multiplet), 3,11 (3H, singlet), with 3.79 (3H, singlet), 5,04 5,01 (1H, multiplet), to 5.85 (1H, doublet, J 8 Hz), 6,23 (1H, doublet, J 8 Hz), 6,83 6,87 (2H, multiplet), 7,12 to 7.35 (7H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3312, 294, 1669, 1644, 1511, 1248, 1033, 700.

Example 96. N-/2-phenyl-1-(2-thienyl)-ethyl/- 3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 45 was obtained in a manner analogous to the one described in example 1, the interaction of 3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid and 2-phenyl-1-(2-thienyl)-ethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.45 and 0.61 (all 3H, each singlet), of 1.07 (3H, singlet), 4,7 5,7 (4H, multiplet), 6,7 7,4 (8H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 1663, 1602.

Example 97. N-/(S)-1,2-diphenylether/- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.51 (3H, singlet), were 0.94 (3H, singlet), 0,90 2,20 (N, multiplet), 3,11 3,00 (2H, multiplet), and 3.31 (1H, triplet, J 8 Hz), 5,22 5,31 (1H, multiplet), vs. 5.47 (1H, broad band), 5,59 (1H, doublet, J 7 Hz), 5,80 (1H, doublet, J 10 Hz), 6,77 (1H, doublet, J 10 Hz), 7,0 to 7.35 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3225, 2931, 1667, 1602, 1495, 1475, 1453, 1220, 825, 698.

Example 98. N-/(S)-1,2-diphenylether/- 3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

The connection specified in the title of the example, with a yield of 99 was obtained in a manner analogous to the one described in example 1, the interaction of 3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid and (S)-1,2-diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.54 (3H, singlet), of 1.07 (3H, singlet), of 1.07 (3H, singlet), 0,80 2,60 (N, multiplet), 3,00 3,20 (2H, multiplet), 4,77 4,80 (1H, multiplet), 5,23 5,31 (1H, multiplet), ceiling of 5.60 (1H, doublet, J 7 Hz), 7,00 7,40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 29430 1677, 1660, 1640, 1518, 1496, 1454, 1386, 1223, 699.

Example 99. N-/(S)-1,2-diphenylether/- 4-methyl-3-oxo-4-Aza-5-alpha-androstane--17-beta-carboxamide.

The connection specified in the title of the example, exit 77 polycarbonates acid, obtained as described in the example of a parent compounds 2, with (S)-1,2-diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.50 (3H, singlet) to 0.85 (3H, singlet), 0,70 2,20 (N, multiplet), 2,40 - of 2.50 (2H, multiplet), of 2.92 (3H, singlet), 2,99 3,17 (3H, multiplet), of 5.26 (1H, Quartet, J 7 Hz), to 5.58 (1H, doublet, J 7 Hz), 7.03 is 7,34 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3318, 2941, 1645, 1528, 1495, 1454, 1393, 1305, 1228, 1031, 757, 700.

Example 100. N-/(S)-1,2-diphenylether/- 4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 90 was obtained by the method similar to that described in example 1, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid, obtained in the example of a parent compounds 4, with (S)-1,2-diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.51 (3H, singlet), to 0.89 (3H, singlet), 0,90 2,20 (N, multiplet), to 2.94 (3H, singlet), to 3.33 (1H, doublet of doublets, J 13 and 4 Hz), 5,22 5,31 (1H, multiplet), 5,59 (1H, doublet, J 7 Hz), of 5.84 (1H, doublet, J 10 Hz), of 6.65 (1H, doublet, J 10 Hz), 7,00 7,40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3320, 2941, 1659, 1603, 1525, 1495, 1453, 12>The connection specified in the title of the example, with the release of 91 was obtained by the method similar to that described in example 1, the interaction of 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid, obtained in example retrieve the source of the compounds 5, c (S)-1,2-diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.53 (3H, singlet), a 1.01 (3H, singlet), 0,90 2,30 (N, multiplet), 2,49 - of 2.54 (2H, multiplet), 3,11 (3H, singlet), 3,05 3,20 (2H, multiplet), of 5.00 to 5.03 (1H, multiplet), 5,27 (1H, Quartet, J 7 Hz), ceiling of 5.60 (1H, doublet, J 7 Hz), 7,00 7,40 (10H, multiplet).

Range of the infrared absorption (KBr),maxcm-1: 3402, 2949, 1648, 1624, 1520, 1468, 1361, 1267, 760, 700.

Example 102. N-/(R)-1,2-diphenylether/- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 73 was obtained by the method similar to that described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid with (R)-1,2-diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0,46 (3H, singlet), of 0.95 (3H, singlet), 0,90 1,80 (14N, multiplet), 2,00 - 2,25 (2H, multiplet), 2,95 of 2.23 (2H, multiplet), and 3.31 (1H, triplet, J 7 Hz), 5,30 to 5.55 (3H, multiplet), of 5.82 (1H, doublet, J 10 Hz), 6,79 (1H, doublet, J 10 Hz), 7,10 7,40 (10H, mu is 8.

Example 103. N-/(R)-1,2-diphenylether/- 3-oxo-4-Aza-5-alpha-androst-5-ene-17-beta-carboxamide.

The connection specified in the title of the example was obtained with the yield of 80 manner similar to that described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid and (R)-1,2-diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.49 (3H, singlet), a 1.08 (3H, singlet), 0,90 2,30 (N, multiplet), 2,40 - 2,60 (2H, multiplet), 2,90 of 3.25 (2H, multiplet), 4,67 rate 4.79 (1H, multiplet), 5,30 5,38 (1H, multiplet), of 5.50 (1H, doublet, J 8 Hz), 7,10 - 7,40 (11N, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3185, 2945, 1670, 1495, 1454, 1386, 1222, 832, 760, 699.

Example 104. N-/(R)-1,2-diphenylether/- 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 96 was obtained by the method similar to that described in example 1, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid, obtained as described in example obtain compounds 2, with (R)-1,2-diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0,46 (3H, singlet), of 0.87 (3H, singlet), 0,70 2,20 (N, multiplet), 2,30 - of 2.50 (2H, multiplet), of 2.92 (3H, singleowner in the infrared region (KBr),maxcm-1: 3317, 2939, 164, 1527, 1495, 1453, 1392, 1305, 1228, 1032, 699.

Example 105. N-/(R)-1,2-diphenylether/- 4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 86 was obtained in a manner analogous to the one described in example 1, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid, obtained as described in the example of a parent compounds 4, with (R)-1,2-diphenylethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 04,6 (3H, singlet), of 0.90 (3H, singlet), 0,80 2,25 (N, multiplet), 2,95 (3H, singlet), 2,90 3,40 (3H, multiplet), from 5.29 5,38 (1H, multiplet), 5,49 (1H, doublet, J 7 Hz), 5,88 (1H, doublet, J 9 Hz), 6,69 (1H, doublet, J 9 Hz), 7,10 7,40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3323, 2940, 1663, 1526, 1495, 1453, 1227, 820, 699.

Example 106. N-/(R)-1,2-diphenylether/- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 82 was obtained by the method similar to that described in example 1, the interaction of 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid, obtained as described in example retrieve the source of the compounds 5, with (R)-1,2-diphenylethylamine.

With the plet), 2,50 - 2,60 (2H, multiplet), 3,11 (3H, multiplet), 2,99-3,20 (2H, multiplet), of 5.00 to 5.03 (1H, multiplet), 5,30 5,38 (1H, multiplet), of 5.50 (1H, doublet, J 7 Hz), 7,10 7,40 (10H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3434, 2940, 1672, 1663, 1649, 1495, 1453, 1389, 758, 701.

Example 107. N-/1-methyl-1-(2-thienyl)-ethyl/- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 27 was obtained in a manner analogous to the one described in example 2, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid with 1-methyl-1-(2-thienyl)-ethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.68 (3H, singlet), of 0.97 (3H, singlet), 0,90 1,85 (N, multiplet), is 1.81 (3H, singlet), is 1.82 (3H, singlet), 2,02 2,07 (2H, multiplet), 3,32 (1H, triplet, J 9 Hz), of 5.39 (1H, broad), of 5.53 (1H, singlet), of 5.81 (1H, doublet, J 10 Hz), 6,79 (1H, doublet, J 10 Hz), 6,91 of 6.99 (2H, multiplet), 7,16 - 7,19 (1H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3253, 2931, 1675, 1656, 1596, 1489, 1453, 817, 700.

Example 108. N-/1-methyl-1-(2-thienyl)-ethyl/- 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 42 was obtained by a method similar to that described in the example is the iMER obtain parent compounds 2, 1-methyl-1-(2-thienyl)-ethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.67 (3H, singlet), or 0.83 (3H, singlet), 0,70 2,25 (N, multiplet), is 1.81 (3H, singlet), is 1.82 (3H, singlet), 2,42 2,47 (2H, multiplet), of 2.92 (3H, singlet), to 3.02 (1H, doublet of doublets, J 12 and 3 Hz), the 5.51 (1H, singlet), 6,91 of 6.99 (2H, multiplet), 7,16 to 7.18 (1H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3312, 2943, 1671, 1627, 1537, 1383, 1227, 707.

Example 109. N-/1-methyl-1-(2-thienyl)-ethyl/- 4-methyl-3-oxo-4-Aza-5-alpha-androst-EN-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 26 was obtained in a manner analogous to the one described in example 2, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid, obtained as described in the example of a parent compounds 4, 1-methyl-(2-thienyl)-ethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.68 (3H, singlet), to 0.92 (3H, singlet), 0,90 1,86 (N, multiplet), is 1.81 (3H, singlet), is 1.82 (3H, singlet), 1,96 2,17 (4H, multiplet), 2,95 (3H, singlet), to 3.34 (1H, doublet of doublets, J 13 and 3 Hz), 5,52 (1H, singlet), 5,86 (1H, doublet, J 10 Hz), of 6.68 (1H, doublet, J 10 Hz), 6,91 of 6.99 (2H, multiplet), 7,16-7,19 (1H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm--beta-carboxamide.

The connection specified in the title of the example, with the release of 50 was obtained by the method similar to that described in example 2, the interaction of 4-methyl-3-oxo-4-Aza-androst-1-ene-17-beta-carboxylic acid, obtained as described in example retrieve the source of the compounds 5, 1-methyl-1-(2-thienyl)-ethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.71 (3H, singlet), of 1.05 (3H, singlet), of 1.05 to 2.29 (M, multiplet), is 1.82 (3H, singlet) and 1.83 (3H, singlet), 2,50 2,55 (2H, multiplet), 3,11 (3H, singlet), 5,04 5,01 (1H, multiplet), 5,54 (1H, singlet), 6,91 of 7.00 (2H, multiplet), 7,16 7,19 (1H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3321, 2966, 1677, 1636, 1522, 1383, 1247, 688.

Example 111. N-/-alpha-(4 oksifenil)-benzyl/- 4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 90 was obtained by the method similar to that described in example 37, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid, obtained as described in the example of a parent compounds 4, alpha-(4 oksifenil)-benzylamine.

Spectrum of nuclear magnetic resonance (CDCl3+ CD2OD), δ, million days of 0.57 (3H, singlet) of 0.91 (3H, singlet), 0,93 2,03 (N, multiplet), 2 doublet, J 10 Hz), 6.75 in to 6.80 (2H, multiplet), 7,01-7,06 (2H, multiplet), then 7.20 to 7.35 (5H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3274, 2943, 1641, 1615, 1599, 1514, 820, 705.

Example 112. N-/-alpha-(4 oksifenil)-benzyl/- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 25 was obtained in a manner analogous to the one described in example 37, the interaction of 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid, obtained as described in example retrieve the source of the compounds 5, alpha-(4 oksifenil)-benzylamino.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0,70 (3H, singlet), was 1.04 (3H, singlet), 1,07 2,30 (17H, multiplet), 2,49 is 2.55 (2H, multiplet), of 3.12 (3H, singlet), 5,04 (1H, doublet of doublets, J 5 and 2 Hz), by 5.87 (1H, doublet, J 8 Hz), of 6.20 (1H, doublet, J 8 Hz), 6.73 x is 6.78 (2H, multiplet), 7,02 7,07 (2H, multiplet), 7,22 of 7.36 (5H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3282, 2946, 1628, 1595, 1517, 1452, 1274, 1239, 701.

Example 113. N-/(S)-1-phenyl-2-(4-were)ethyl/- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 71 was obtained by the method similar to the one used in example 1, entries batch is the range of nuclear magnetic resonance (CDCl3Delta, million days of 0.51 (3H, singlet), were 0.94 (3H, singlet), 0,90 2,20 (N, multiplet), of 2.28 (3H, singlet), 3,07 3,00 (2H, multiplet), and 3.31 (1H, triplet, J 7 Hz), 5,23 (1H, doublet of doublets, J 14 and 7 Hz), of 5.40 (broad band), to 5.58 (1H, doublet, J 7 Hz), 5,80 (1H, doublet, J 10 Hz), 6,77 (1H, doublet, J 10 Hz), 6,93 (1H, doublet, J 8 Hz), 7,03 (2H, doublet, J 8 Hz), 7,19 7,33 (5H, multiplet).

Absorption spectrum in the infrared region (KBr), maxcm-1: 3438, 3226, 2931, 1683, 1607, 1475, 698.

Example 114. N-/(S)-1-phenyl-2-(4-were)-ethyl/- 3-oxo-4-Aza-5-alpha-androst-5-ene-17-beta-carboxamide.

The connection specified in the title of the example, exit 81 was obtained in a manner analogous to the one described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid and (S-1-phenyl-2-(4-were)-ethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.54 (3H, singlet), of 1.07 (3H, singlet), 1,00 2,60 (N, multiplet), of 2.28 (3H, singlet), of 3.00 to 3.09 (2H, multiplet), 4,76 rate 4.79 (1H, multiplet), of 5.34 (1H, doublet of doublets, J 14 and 7 Hz), to 5.58 (1H, doublet, J 7 Hz), 6,93 (2H, doublet, J 8 Hz), 7,03 (2H, doublet, J 8 Hz), 7,17 7,33 (5H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3420, 3140, 2944, 1678, 1660, 1637, 1518, 707.

Example 115. N-/(S)-1-phenyl-2-(4-were)-ethyl/- 3-oxo-4-Aza-5-alpha-androst-analogichnym described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid, obtained as described in the example of a parent compounds 4, with (S)-1-phenyl-2-(4-methyl-phenyl)-ethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.51 (3H, singlet), to 0.89 (3H, singlet), 0,80 2,20 (N, multiplet), of 2.28 (3H, singlet), to 2.94 (3H, singlet), 3,02 of 3.07 (2H, multiplet), to 3.33 (1H, doublet of doublets, J 13 and 3 Hz), 5,20 5,30 (1H, multiplet), to 5.57 (1H, doublet, J 7 Hz), by 5.87 (2H, doublet, J 10 Hz), 0,66 (1H, doublet, J 10 Hz), 6,93 (2H, doublet, J 8 Hz, 7,03 (2H, doublet, J 8 Hz), 7,19 7,33 (5H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3359, 2954, 1651, 1598, 1525, 1448, 700.

Example 116. N-/(S)-1-phenyl-2-(4-were)-ethyl/- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 58 was obtained by the method similar to that described in example 1, the interaction of 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid, obtained as described in example retrieve the source of compounds 5 with (S)-1-phenyl-2-(4-were)-ethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.53 (3H, singlet), a 1.01 (3H, singlet), 1,05 of 2.27 (M, multiplet), of 2.28 (3H, singlet), 2,49 of 2.54 (2H, multiplet), 3,03 of 3.07 (2H, mo,93 (2H, doublet, J 8 Hz), 7,03 (2H, doublet, J 8 Hz), 7,19 7,33 (5H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3396, 2945, 1665, 164, 1627, 1519, 1471, 704.

Example 117. N-/(S)-1-diphenylmethyl)- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

640 mg of N-diphenylmethyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide was dissolved in 20 ml of dry dioxane and the resulting solution was added 310 mg of 2,3-dichloro-5,6-dicyano-para-benzoquinone and 1356 mg and 11.0-bis-(trimethylsilyl)-trifurcated. The resulting solution was then stirred at room temperature for 4 h, after which it was heated under reflux for 13 hours Then the reaction mixture was cooled to room temperature and diluted with 100 ml methylene chloride. Then washed with water, aqueous sodium bicarbonate solution and saturated aqueous sodium chloride in that order, then dried over anhydrous magnesium sulfate and are condensed by evaporation under reduced pressure. The obtained residue was purified by chromatography on a column of 15 g of silica gel. Gradient elution with mixtures of acetone methylene chloride in ratios from 1 9 to 2 3 to get the 360 mg of the target compound.

Spectrum of nuclear magnetic resonance ukazannoj is(4-acetamidophenyl)-1-(methylacyl)- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 73 was obtained by the method similar to that described in example 37, the interaction of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid and 4-(1-amino-1-methylethyl)-ndimethylacetamide.

Spectrum of nuclear magnetic resonance (CDCl3+ CD3OD), δ, million days of 0.65 (3H, singlet), to 0.89 (3H, singlet), 0,75 2,20 (N, multiplet), of 1.65 (3H, singlet), by 1.68 (3H, singlet) by 2.13 (3H, singlet), 2,37 2,43 (2H, multiplet), was 3.05 (1H, doublet of doublets, J 12 and 4 Hz), 7,31 (2H, doublet, J 8 Hz), 7,45 (2H, doublet, J 8 Hz).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3303, 3194, 2490, 2817, 1698, 1672, 1609. 1546, 1495, 1405, 829, 560.

Example 119. N-/1-(4-acetamidophenyl)-1-methylethyl/- 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 59 was obtained in a manner analogous to the one described in example 37, the interaction of 3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid and 4-(1-amino-1-methylethyl)-acetanilide.

Spectrum of nuclear magnetic resonance (CDCl3+ CD3OD), δ, h in million of 0.66 (3H, singlet), of 0.97 (3H, singlet), 1,00 2,20 (N, multiplet), of 1.66 (3H, singlet), by 1.68 (3H, singlet) by 2.13 (3H, singlet), 3,32 (1H, double doublet, J 9 and 6 Hz), 5,80 (1H, doublet, J 10 Hz), PC 6.82 (1H, doublet, J 10 Hz), 7,32 (23, 2936, 1707, 1672, 1606, 1545, 1495, 1321, 882, 561.

Example 120. N-/1-(4-acetamidophenyl)-1-methylethyl/- 3-oxo-4-Aza-5-alpha-androst-5-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 50 was obtained by the method similar to that described in example 37, the interaction of 3-oxo-4-Aza-5-alpha-androst-5-ene-17-beta-carboxylic acid and 4-(1-amino-1-methylethyl)-acetanilide.

Spectrum of nuclear magnetic resonance (CDCl3+ CD3OD), δ, h in million of 0.68 (3H, singlet), 1,10 (3H, singlet), 1,00 2,50 (N, multiplet), of 1.66 (3H, singlet), by 1.68 (3H, singlet), to 2.18 (3H, singlet), 7,32 (2H, doublet, J 9 Hz), 7,45 (2H, doublet, J 9 Hz).

Absorption spectrum in the infrared region (KBr),maxcm-1: 330, 3194, 2939, 1705, 1671, 1610, 1574, 1495, 1387, 1225, 830, 561.

Example 121. N-/1-(4-acetamidophenyl)-1-methylethyl/- 4-methyl-3-oxo-4-Aza-5-alpha-androst-5-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 40 was obtained by the method similar to that described in example 37, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androst-5-ene-17-beta-carboxylic acid, obtained as described in the example of a parent compounds 2, 4-(1-amino-1-methylethyl)-acetanilide.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.66 (3H, singable doublets, J 12 and 3 Hz), 5,54 (1H, broad), 7,33 (2H, doublet, J 8 Hz), 7,42 (2H, doublet, J 8 Hz).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3305, 2938, 1688, 1673, 1623, 1530, 1398, 1318, 1252, 834, 557.

Example 122. N-/1-(4-acetamidophenyl)-1-methylethyl/- 4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 67 was obtained in a manner analogous to the one described in example 37, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androst-5-ene-17-beta-carboxylic acid, obtained as described in the example of a parent compounds 4, 4-(1-amino-1-methylethyl)-acetanilide.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.67 (3H, singlet), of 0.93 (3H, singlet), 0,90 2,20 (17H, multiplet), to 1.67 (3H, singlet), to 1.70 (3H, singlet), 2,17 (3H, singlet), 2,96 (3H, singlet), to 3.35 (1H, doublet of doublets, J 13 and 5 Hz), 5,54 (1H, broad), of 5.89 (1H, doublet, J 10 Hz), 6,69 (1H, doublet, J 10 Hz), 7,33 (2H, doublet, J 8 Hz), 7,42 (2H, doublet, J 8 Hz).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3309, 2971, 2936, 1689, 1675, 1605, 1534, 1315, 1255, 824.

Example 123. N-/1-(4-acetamidophenyl)-1-methylethyl/- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 61 was obtained by a method similar is Oh as described in the example of a parent compounds 5, and 4-(1-amino-1-methylethyl)-acetanilide.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days is 0.69 (3H, singlet), and 1.63 (3H, singlet), 1,00 2,30 (17H, multiplet), to 1.67 (3H, singlet), to 1.70 (3H, singlet), of 2.15 (3H, singlet), 2,58 2,50 (2H, multiplet), of 3.12 (3H, singlet), 5,04 (1H, doublet of doublets, J 5 and 2 Hz), of 5.55 (1H, broad), 7,34 (2H, doublet, J 8 Hz), 7,41 (2H, doublet, J 8 Hz).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3302, 2958, 1667, 1653, 1641, 1529, 1382, 1319, 1264, 835, 560.

Example 124. N-(4,4-dimethoxyphenethyl)- 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxamide.

Indicated in the name of the example compound 50 output was obtained in a manner analogous to the one described in example 1, the interaction of 4-methyl-3-oxo-4-Aza-androst-5-ene-17-beta-carboxylic acid and 4,4-dimethoxyphenethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million D. 0,70 (3H, singlet), of 1.09 (3H, singlet), 1,10 2,30 (20N, multiplet), 2,45 - of 2.50 (2H, multiplet), with 3.79 (3H, singlet), 4,77 rate 4.79 (1H, multiplet), of 5.81 (1H, doublet, J 8 Hz), 6,18 (1H, doublet, J 8 Hz), 6,82 to 6.88 (4H, multiplet), 7,11 to 7.18 (4H, multiplet).

Absorption spectrum in the infrared region (KBr), maxcm-1: 1662, 1609, 1511, 1488, 1248, 176, 1035, 831.

Example 125. N-(4-methoxyphenethyl)- 4-methyl-3-oxo-4-Aza-5-alpha--Andro is, similar to that described in example 1, the interaction of 4-methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid, obtained as described in the example of a parent compounds 4, 4-methoxybenzylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.68 (3H, singlet), to 0.92 (3H, singlet), 0,90 of 1.88 (M, multiplet), 1,90 - 2,10 (2H, multiplet), 2,17 of 2.30 (2H, multiplet), 2,95 (3H, singlet), to 3.34 (1H, doublet of doublets, J 13 and 3 Hz), with 3.79 (3H, singlet), of 5.83 by 5.87 (1H, multiplet), to 5.85 (1H, doublet, J 10 Hz), 6,23 (2H, doublet, J 8 Hz), 6,66 (1H, doublet, J 10 Hz), 6,83 6,87 (2H, multiplet), 7,16 7,12 (2H, multiplet), 7,20 of 7.36 (5H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3312, 2939, 1663, 1604, 1511, 1248, 820, 699.

Example 126. N-(4,4-dimethoxyphenethyl)- 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxamide.

The connection specified in the title of the example, with the release of 51 was obtained in a manner analogous to the one described in example 1, the interaction of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid and 4,4-dimethoxyphenethylamine.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.67 (3H, singlet), to 0.89 (3H, singlet), 0,70 2,35 (N, multiplet), 2,37 is 2.43 (2H, multiplet), 3,4 (1H, doublet of doublets, J 11 and 4 Hz), of 3.78 (3H, single).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3305, 2936, 1659, 1511, 1247, 1175, 1034, 830.

Obtaining 1. Methyl-4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylate.

Suspension is 5.18 g of methyl ester of 3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid in 74 ml of dimethylformamide was added dropwise to a suspension of 0.82 g of sodium hydride (as a 55 weight dispersion in mineral oil) in 30 ml of dry dimethylformamide at room temperature and the suspension was stirred at 70o1 o'clock At the expiration of this time was added dropwise 22.1 g iodotope bromide to the mixture at room temperature and the mixture was stirred at room temperature for 100 min, then at 70oWith a further 1 h Then the reaction mixture was diluted with diethyl ether, twice washed with water and saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, then the solvent is kept at reduced pressure. The obtained residue was purified column chromatography through 290 g of silica gel. Gradient elution with mixtures of acetone and methylene chloride in the range of ratios from 1 5 to 1 2 to get the 2,95 g of compound indicated in the title of the example.

Spectrum of nuclear magnetic resonance (CDCl3< J 12 and 3 Hz), 5,67 (3H, singlet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2932, 1732, 1649, 1209.

Getting 2. 4-Methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid.

1.68 g of potassium hydride (purity 85 by weight), and 3.0 ml of water was added to the solution to 2.94 g of methyl ester of 4-methyl-3-oxo-4-Aza-5-alpha-androstane-17-beta-carboxylic acid, obtained as described in the example of a parent compounds 1, 12.1 ml of methanol and the mixture was stirred 3 h at reflux. After this time the reaction mixture are condensed by evaporation under reduced pressure. The obtained residue was acidified by adding hydrochloric acid. The crystals deposited precipitates were collected by filtration, washed with water and dried in the air, getting 2.20 g of the compound indicated in the title of the example.

Spectrum of nuclear magnetic resonance (CDCl3+ CD3OD), Delta, including million to 0.72 (3H, singlet), to 0.88 (3H, singlet), 0,75 2,60 (N, multiplet), with 2.93 (3H, singlet), of 3.07 (1H, doublet of doublets, J 12 and 3 Hz).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2938, 1716, 1604, 1212, 1191, 723.

Getting 3. Methyl ester-4-Methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid.

oC for 30 minutes, after this time the suspension at room temperature was added dropwise at 13.0 g of methyl iodide and the mixture was stirred at room temperature for 2.5 hours the Reaction mixture was then diluted with diethyl ether, washed with water (three times) and saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, then the solvent is kept at reduced pressure. The obtained residue was purified column chromatography through 160 g of silica gel. Gradient elution with mixtures of acetone and methylene chloride in the range of ratios from 1 20 to 1 2 to get the 2.15 g of the compound indicated in the title of the example.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.68 (3H, singlet), to 0.92 (3H, singlet), 0,88 2,20 (15 NM, multiplet), a 2.36 (1H, triplet, J 9 Hz), 2,96 (3H, singlet), to 3.36 (1H, doublet of doublets, J 13 and 4 Hz), to 3.67 (3H, singlet), 5,91 (1H, doublet, J 10 Hz), of 6.71 (1H, doublet, J 10 Hz).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2944, 1729, 1600, 1606, 1423, 1218, 1199, 1174, 1154, 822.

Getting 4. 4-Methyl-3-oxo-4-Aza-5-alpha-androst-1-ene-17-beta-carboxylic acid.

1.22 g of potassium hydroxide (purity 85 by weight) in 2.2 ml of water was added to a solution of 2.15 g of methyl ester 4 is similar compounds 3, and 8.8 ml of dioxane and the mixture was stirred at reflux for 3 hours, after this time the reaction mixture are condensed by evaporation under reduced pressure. The obtained residue was acidified by addition of aqueous hydrochloric acid. Precipitated precipitated crystals were collected by filtration, washed with water, dried in air and received 2.15 g of the compound indicated in the title of the example.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days to 0.73 (3H, singlet), to 0.92 (3H, singlet), 0,80 2,20 (N, multiplet), is 2.37 (1H, triplet, J 9 Hz), 2,96 (3H, singlet), 3,37 (1H, doublet of doublets, J 13 and 3 Hz), 5,88 (1H, doublet, J 10 Hz), 6,74 (1H, doublet, J 10 Hz).

Absorption spectrum in the infrared region (KBr),maxcm-1: 2939, 1713, 1655, 1589, 1451, 1220, 1213, 1199, 823.

Getting 5. 4-Methyl-3-oxo-4-Aza-5-alpha-androst-5-ene-17-beta-carboxylic acid.

37 40 ml volume of a solution of methylamine in methanol was added to the solution 26,0 17-beta-carboxy-5-oxo-A-nor-3,5-SECO-androstane-3-carboxylic acid in 150 ml of ethylene glycol at room temperature and the mixture was stirred at the same temperature for 30 minutes and Then the reaction mixture was gradually heated to 180oWith under stirring and the stirring was continued at 180oWith 3 more water. Precipitated precipitated crystals were collected by filtration, washed with water, dried in the air and got to 22.0 g of the target compound.

Spectrum of nuclear magnetic resonance (CDCl3Delta, million days of 0.77 (3H, singlet), of 1.05 (3H, singlet), 1,00 2,70 (N, multiplet), of 3.13 (3H, singlet), 5,03 of 5.06 (1H, multiplet).

Absorption spectrum in the infrared region (KBr),maxcm-1: 3459, 2943, 1726, 1616, 1474, 1393, 1329, 1230, 1168, 1057.

Experimental example.

1. Getting 5-alpha-reductase from prostate glands of rats.

Lobe of the prostate gland of adult male rats (weight 350 450 g line Spraque-Dauley) cut small pieces with scissors. 1 weight. including pieces of fabric were added to about 3 weight. including buffer solution (20 mmol phosphate potassium buffer solution, pH 7.4, containing 0.33 M sucrose, 1 mmol of dithiothreitol, 50 µmol nicotinamide-adenine-dinucleotide-phosphate (N) and 0.001 fluoride phenylmethylsulfonyl (PMSF) and the mixture is homogenized at first through the homogenizer Polytron (trademark, K1NEMATICA ImbH) and then using a glass Teflon homogenizer (trademark). Gomogenizirovannogo thus the tissue of the prostate gland then centrifuged (140000 g, 60 min) for sedimentation.

About 3 wt. is ova was centrifuged (14000 g, 60 min) for washing and separating the precipitate, which was considered as the drug of 5-alpha-reductase in rats. To the precipitate was added a sufficient amount of the above buffer solution to the protein content in the solution is between 10 and 40 mg/ml Then the solution was frozen and stored at -80oC. the protein Content was determined by bis-happy-protein analysis, in which gamma-globulin bovine serum (Gohn Fradion II, Sigma) was used as protein standard.

2. Test for inhibition of 5-alpha-reductase rats.

5 μl of dimethyl sulfoxide or ethanol, which was dissolved subject to the test compound, was added to 05, ml, 40 mmol buffer solution of potassium phosphate (pH 6.5) containing 5-alpha-reductase rats (the protein content of 1 mg), 1 µmol labeled with carbon-14 testosterone, 1 mmol of dithiothreitol and 500 µmol nicotinamide-adenine-dinucleotide-phosphate (final concentration of test compound (10-8mol and incubated for 15 to 30 min at 37oC. as a control, one sample was added only solvent. Then to terminate the reaction was added 2 ml of ethyl acetate containing 5 μg of testosterone, 5-alpha-dihydrotestosterone and Androstenedione each. Mixture C entre is about evaporated to dryness while blowing nitrogen gas. Steroids were dissolved in 40 μl of ethyl acetate. The solution was applied spots on the plate for thin-layer chromatography (silica plate LK5DF, Whatman) and showed a mixture of ethyl acetate and cyclohexane in the ratio of 1 to 1 by volume, twice at room temperature. Steroid fraction was identified by the appearance of staining under ultraviolet irradiation or by heating with a solution of 1 cesium sulfate and 10 sulfuric acid. The radioactivity on the plate for thin-layer chromatography was measured by analyzer assay (Fuji Film Co. Ltd). The enzyme activity was presented as the number (reaction rate) labeled with carbon-14 5-alpha-dihydrotestosterone, formed from the initially added labeled with carbon-14 testosterone. Inhibiting activity of the test sample in relation to the 5-alpha-reductase equal (the rate of conversion of experimental group / the rate of conversion of the control group) x 100

The results are presented in table.4.

1. Azasteroid compounds of General formula I

< / BR>
where R1H, unsubstituted C1C4-alkyl or benzyl;

R2C1C4-alkyl, substituted phenyl, shriley or thienyl group;

R3H, resumes is whether R3C3-C6alkenyl; carbon-carbon single or double connection, and these phenyl groups may be substituted by at least one Deputy, such as C1C6-alkyl, C1C4-alkoxy, C2C4-alkoxycarbonyl, hydroxy-, halogen-, acetaminophe.

2. Azasteroid of compound I on p. 1, characterized in that they are chosen from the group comprising N-(1,2-diphenylether)-3-oxo-4-Aza-5-androstane-17b-carboxamide, N-(diphenylmethyl)-3-oxo-4-Aza-5a-androstane-17b-carboxamide,

N-(1,1-diphenylether)-3-oxo-4-Aza-5a-androstane-17b-carboxamide, N-(diphenylmethyl)-4-methyl-3-oxo-4-Aza-5a-androstane-17b-carboxamide, N-(1,2-diphenylmethyl)-4-methyl-3-oxo-4-Aza-5a-androstane-17b-carboxamide, N-(1-methyl-1-phenylethyl)-3-oxo-4-Aza-5a-androstane-17b-carboxamide, N-[1-methyl-1-(2-thienyl)-ethyl] -3-oxo-4-Aza-5a-androstane-17b-carboxamide, N-[1-methyl-1-(2-thienyl)-ethyl] -4-methyl-3-oxo-4-Aza-5a-androstane-17b-carboxamide, N-(1-methyl-1-phenylethyl)-4-methyl-3-oxo-4-Aza-5a-androstane-17b-carboxamide, N-[2-(4-were)-1-phenylethyl] -4-methyl-3-oxo-4-Aza-5a-androstane-17b-carboxamide, N-[a-(4-were)-1-phenylethyl]-3-oxo-4-Aza-5a-androstane-17b-carboxamide, N-(1,1-diphenylether)-4-methyl-3-oxo-4-Aza-5a-androstane-17b-carboxamide, N-[a-(4 oksifenil)-benzyl] -3-oxo-4-Aza-5a-EN the-1-methylethyl]-3-oxo-4-Aza-5a-androstane-17b-carboxamide, N-[1-(4-methoxyphenyl)-1-methylethyl]-4-methyl-3-oxo-4-Aza-5a-17b-carboxamide, N, N-diphenyl-3-oxo-4-Aza-5a-androstane-17b-carbonhydrate, N, N-diphenyl-4-methyl-3-oxo-4-Aza-5a-androstane-17b-carbohydrazide, N-[1-(3-methoxyphenyl)-1-methylethyl] -4-methyl-3-oxo-4-Aza-5a-androstane-17b-carboxamide, N-[1-methyl-1-(2-furyl)-ethyl] -3-oxo-4-Aza-5a-androstane-17b-carboxamide, N-(1,2-diphenylether)-3-oxo-4-Aza-5a-androst-1-EN-17b-carboxamide, N-(1,2-diphenylether)-4-methyl-3-oxo-4-Aza-5a-androst-1-EN-17b-carboxamide, N-(diphenylmethyl)-3-oxo-4-Aza-5a-androst-1-EN-17b-carboxamide, N-(diphenylmethyl)-4-methyl-3-oxo-4-Aza-5a-androst-1-EN-17b-carboxamide, N-[1-phenyl-2-(4-were)-ethyl]-3-oxo-4-Aza-5a-androst-1-EN-17b-carboxamide, N-[1-phenyl-2-(4-were)-ethyl]-4-methyl-3-oxo-4-Aza-5a-androst-1-EN-17b-carboxamide, N-(1,1-diphenylether)-3-oxo-4-Aza-5a-androst-1-EN-17b-carboxamide, N-(1,1-diphenylether)-4-methyl-3-oxo-4-Aza-5a-androst-1-EN-17b-carboxamide, N-(1-methyl-1-phenylethyl)-3-oxo-4-Aza-5a-androst-1-EN-17b-carboxamide, N-(1-methyl-1-phenylethyl)-4-methyl-3-oxo-4-Aza-5a-androst-1-EN-17b-carboxamide, N-[1-methyl-1-(2-thienyl)-ethyl [3-oxo-4-Aza-5a-androst-1-EN-17b - carboxamide, N-[1-methyl-1-(2-thienyl)-ethyl] -4-methyl-3-oxo-4-Aza-5a-androst-1-EN-17b - carboxamide, N-[a-(4 oksifenil)-benzyl]-3-oxo-4-Aza-5a-androst-1-EN-17b-carboxamide, N-[1-(4 oksifenil)-benzyl-4-methyl-3-oxo-4-Aza-xifer)-1-methylethyl]-4-methyl-3-oxo-4-Aza-5a-androst-1-- ene-17b-carboxamide, N-(2-hydroxy-1,2-diphenylether)-3-oxo-4-Aza-5a-androst-1-EN-17b-carboxamide, N,N-diphenyl-3-oxo-4-Aza-5a-androst-1-EN-17b-carbohydrazide, N, N-diphenyl-4-methyl-3-oxo-4-Aza-5a-androst-1-EN-17b-carbohydrazide, N-[1-(2-methoxyphenyl)-1-methylethyl]-3-oxo-4-Aza-5a-androst-1-EN-17b - carboxamide, N-[1-methyl-1-(2-furyl)-ethyl]-3-oxo-4-Aza-5a-androst-1-EN-17b-carboxamide, N-(1,2-diphenylether)-3-oxo-4-Asandros-5-ene-17b-carboxamide, N-(1,2-diphenylether)-4-methyl-3-oxo-4-Asandros-5-ene-17b-carboxamide, N-(diphenylmethyl)-3-oxo-4-Asandros-5-ene-17b-carboxamide, N-(diphenylmethyl)-4-methyl-3-oxo-4-Asandros-5-ene-17b-carboxamide, N-[2-(4-were)-1-phenylethyl] -3-oxo-4-Asandros-5-ene-17b-carboxamide, N-[2-(4-were)-1-phenylethyl]-4-methyl-3-oxo-4-androst-5-ene-17b - carboxamide, N-(1,1-diphenylether)-3-oxo-4-Asandros-5-ene-17b-carboxamide, N-(1,1-diphenylether)-4-methyl-3-oxo-4-Asandros-5-ene-17b-carboxamide, N-(1-methyl-1-phenylethyl)-3-oxo-4-Asandros-5-ene-17b-carboxamide, N-(1-methyl-1-phenetyl)-4-methyl-3-oxo-4-Asandros-5-ene-17b-carboxamide, N-[1-methyl-1-(2-thienyl)-ethyl] -3-hydroxy-4-Asandros-5-ene-17b-carboxamide, N-[1-methyl-1-(2-thienyl)-ethyl] -4-methyl-3-oxo-4-Asandros-5-ene-17b - carboxamide, N-[a-(4 oksifenil)-benzyl] -3-oxo-4-Asandros-5-ene-17b-carboxamide, N-[a-(4 oksifenil)-benzyl]-4-methyl-3-oxo-4-Asandros-5-ene-17b - carboxamide, N-[1-(4-methoxyphenyl)-1-METI Roxane, N-(2-hydroxy-1,2-diphenylether)-4-methyl-3-oxo-4-Asandros-5-ene-17b - carboxamide, N,N-diphenyl-3-oxo-4-Asandros-5-ene-17b-carbohydrazide, N,N-diphenyl-4-methyl-3-oxo-4-Asandros-5-ene-17b-carbohydrazide, N-[1-(3-methoxyphenyl)-1-methylethyl]-3-oxo-4-Asandros-5-ene-17b - carboxamide, N-[1-(2-methoxyphenyl)-1-methylethyl] -4-methyl-3-oxo-4-Asandros-5 - ene-carboxamide and N-[1-methyl-1-(2-furyl)-ethyl]-4-methyl-3-oxo-4-Asandros-5-ene-17b - carboxamide.

3. Compound I under item 1, with the ability to inhibit 5-reductase.

 

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2 cl, 1 ex

FIELD: organic chemistry of steroids, chemical technology.

SUBSTANCE: invention relates to the improved method for preparing chemical compounds of steroid order, namely, to a method for preparing epibrassinolide representing (22R,23R,24R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostane-6-one and relating to biologically active substance - a phytostimulator regulating growth of plants. Method involves the successive carrying out the following stages: a) synthesis of ergosterol mesylate by treatment of ergosterol with methanesulfochloride in pyridine; b) synthesis of isoergosterol by boiling ergosterol mesylate in aqueous acetone in the presence of potassium (sodium) hydrocarbonate; c) synthesis of isoergosterone by oxidation of isoergosterol with chrome anhydride in pyridine; d) synthesis of 7,8-dihydroergosterol by reduction of isoergosterone with sodium dithionite in the presence of a solubilizing medium containing cationic, anionic or nonionic surface-active substances of the following order: CnH2n+1X wherein n = 9-18; X means -NMe3, -NEt3, -COOH, -SO3H, -OSO2M, -OP(O)(OM)2 wherein M means alkaline metal, polyethylene glycol, (C2-C6)-aliphatic alcohols or monoesters of ethylene glycol or diethylene glycol as a co-solubilizing agent, electrolyte and water taken in the molar ratio = 1:(5-6):(100-250), respectively; e) steroid rearrangement of 7,8-dihydroisoergosterol; f) formation of 24-epicastasterone by treatment of (22E,24R)-5α-ergosta-2,22-diene-6-one with methanesulfoneamide and potassium carbonate with using catalytic amounts of potassium ferricyanide (III) and osmium tetraoxide; g) dissolving 24-epicastasterone formed in chloroform followed by treatment with trifluoroperacetic acid forming in mixing trifluoroacetic anhydride and hydrogen peroxide in chlorinated organic solvent, and isolation of the end product of the formula (I) with high yield.

EFFECT: improved preparing method.

2 cl, 7 ex

FIELD: organic chemistry, steroids, medicine, pharmacy.

SUBSTANCE: invention describes novel halogen- and pseudohalogen-substituted 17-methylene-4-azasteroids of the general formula (I) wherein each R20 and R20a means independently fluorine, chlorine, bromine atom, (C1-C4)-alkyl, hydrogen atom (H), cyano-group; R4 and R10 mean hydrogen atom or methyl group; both R1 and R2 represent hydrogen atom and form an additional bond. Compounds are inhibitors of 5α-reductase and can be used in treatment of diseases caused by the enhanced blood and tissue testosterone and dihydrotestosterone level.

EFFECT: valuable medicinal and biochemical properties of compounds.

9 cl, 5 dwg, 1 tbl, 10 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention describes compound of the formula (I) or its pharmaceutically acceptable salt, or an enantiomer wherein n = 0 or 1; a - b means -CF=CH or -CHFCH2; R1 represents (C1-C3)-alkyl wherein alkyl is unsubstituted; R2 represents hydrogen atom; R3 is chosen from (C1-C4)-alkyl, (CH2)n-cycloheteroalkyl and (CH2)n-aryl; or R2 and R3 form in common 6-membered saturated ring condensed with 5-membered aromatic ring system comprising 2 heteroatoms chosen from nitrogen atom (N), and pharmaceutical compositions. Compounds of the formula (I) represent modulators of androgen receptors (AR) possessing tissue-selective effect. Proposed compounds are useful as androgen receptors agonists in osseous and/or muscle tissue in antagonizing AR in male patient prostate or in female patient uterus.

EFFECT: valuable medicinal properties of compounds and pharmaceutical composition.

36 cl, 2 tbl, 72 ex

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention describes an improved method for synthesis of 17β-substituted 4-azaandrost-1-en-3-one of the general formula (I): wherein R means -OH, (C1-C4)-alkyl, (C1-C4)-alkenyl, phenyl, benzyl and others, or their pharmaceutically acceptable salts. Method involves insertion protective groups into 3-keto-4-aza (lactam) form of compound of the general formula (II): wherein R has indicated values to form compound of the general formula (III): wherein R3 means trialkylsilyl, or in common with R4 residue -C(O)-C(O)- or -C(O)-Y-C(O)- wherein R4 means tert.-butyloxycarbonyl preferably; Y means -(CH2)n wherein n = 1-4, or ortho-phenylene. Then a synthesized compound is converted in the presence of a dehydrogenation catalyst of in the presence of benzoquinone, allylmethylcarbonate, allylethylcarbonate and/or allylpropylcarbonate, and ▵1-double bond is introduced in 1,2-position followed by removal of protective groups and, if necessary, (when R means -OH) conversion to salts. Method provides the high yield and purity degree of synthesized compounds.

EFFECT: improved method of synthesis.

21 cl, 9 ex

FIELD: chemistry.

SUBSTANCE: description is given of thiomorpholine derivatives of steroids with general formula I . These steroids are characterised by presence of a thiomorpholine fragment, bonded to a C17 steroid skeleton through an alkylene spacer, where R4 and R4' are hydrogen and methyl, under the condition that, both R4 and R4' represent hydrogen at the same time.

EFFECT: invention can be successfully used for stimulating meiosis of human oocyte.

12 cl, 2 ex, 5 tbl, 6 dwg

FIELD: chemistry.

SUBSTANCE: invention refers to production of new tritiated analogues of physiologically active compounds - triterpene glycosides of holothurians Cucumaria of formula: .

EFFECT: there are produced new tritiated analogues of physiologically active compounds.

2 cl, 2 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to racemic 3,17β-dihydroxy-7α,18-dimethyl-6-oxaextra-1,3,5(10),8(9)-tetraene diacetate of formula .

EFFECT: production of the substance exhibiting osteoprotective, hypocholesteremic and antioxidant action with lowered uterotropic activity.

1 cl, 2 ex, 2 tbl, 2 dwg

FIELD: chemistry.

SUBSTANCE: invention relates to novel 4-oxa- and 4-aza-16α, 17α-cyclohexanopregnanes (4-oxa- and 4-aza-pregna-D'-pentaranes), which can be used n medicine to treat malignant tumours, having general formula I , where X=0 or NR, R=R1=R2=R4=H where R1+R3 form a bond. Said compounds are obtained by oxidising ring A 16α, 17α-cyclohexano-progesterone with potassium permanganate and sodium periodate in the presence of sodium carbonate in 5-oxo-A-nor-3,5-secoacid followed by closure of ring A in 4-oxa-16α, 17α-cyclohexanopregn-5-en-20-one while treating with a sodium acetate dehydrating agent in Ac2O and in 4-aza-16α, 17α-cyclohexanopregn-5-en-20-one using ammonium acetate in acetic acid.

EFFECT: compounds are effective inhibitors of oestrogen-stimulated cell proliferation HeLa.

2 cl, 2 ex, 1 tbl

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