Derivatives of 2-arylaryl-(piperidine-4-ylmethyl)amine and drug

 

Describes the derived 2-arylaryl-(piperidin-4-ylmethyl)amine of the formula (I), where R1is hydrogen, halogen atom, alkoxy, haloalkyl containing in the alkyl part is one to twelve carbon atoms, amino group; R2- alkyl, alkyloxy, haloalkyl containing in the alkyl part is one to twelve carbon atoms; halogen atom; nitro-group;- (CH2)pX, where p denotes 0; X is selected from haloalkyl containing from one to twelve carbon atoms, and phenyl; -NR7R8; -NR6R9; -NR6WITH NR7R8; -NR6SO2R9; -NR6SO2NR7R8; -SR9; -SOR9; -SO2R9or R1and R2together with the ring to which they are bound, form a 5 - or 6-membered monocyclic saturated or unsaturated ring, optionally containing 0, 1 or 2 heteroatoms, independently from each other selected from nitrogen atom, oxygen; R3and R4each independently from each other represents lower alkyl or cycloalkenyl containing from four to fourteen carbon atoms, R5denotes a hydrogen atom; -R6; -R7; -CONR7R8- (CH2)nNR6SO2R9; -CSNR; SO2NR6(CH2)nR7n denotes 1 to 6; R6and R7each independently represents a hydrogen atom or lower alkyl, cycloalkyl containing from three to fourteen carbon atoms, phenyl or pyridyl; R9denotes alkyl containing from one to twelve carbon atoms; cycloalkyl, including from three to four carbon atoms; phenethyl; naphthyl; diphenyl; phenyl, unsubstituted or mono-, di - or tizamidine phenyl, the substituents which independently of one another selected from halogen atom; lower alkyl, alkyloxy, haloalkyl containing in the alkyl part is one to twelve carbon atoms; ceanography; nitro; -R7; -NR7R8; -SO2R9; -SO2NR7R8;- (CH2)pX; p represents 0; X - haloalkyl containing from one to twelve carbon atoms; heterocyclyl, represents saturated carbocyclic radical containing five or six ring atoms, of which one or two selected from nitrogen, oxygen and sulfur, optionally substituted by one or two substituents from lower alkyl, hydroxy, hydroxyalkyl containing from one to twelve carbon atoms, carbonyl group, -COR7and-R

Description text in facsimile form (see graphic part).

Claims

1. The derived 2-arylaryl-(piperidine-4-yl-methyl)amine of the formula

where R1denotes a hydrogen atom, alkyloxy containing from one to twelve carbon atoms, halogen atom, haloalkyl containing from one to twelve carbon atoms, or amino group;

R2refers to (1) alkyl containing from one to twelve carbon atoms, (2) alkyloxy containing from one to twelve carbon atoms, (3) halogen atom, (4) haloalkyl containing from one to twelve carbon atoms, (5) a nitro-group, (7) -O(CH2)7R8, (9) -NR6R9, (10) -NR6WITH NR7R8, (13) -NR6SO2R9, (14) -NR6SO2NR7R8, (15) -SR9, (16) -SOR9, (17) -SO2R9or R1and R2together with the ring to which they are bound, form a 5 - or 6-membered monocyclic saturated or unsaturated ring, optionally containing 0,1 or 2 heteroatoms, independently from each other selected from nitrogen atom, oxygen;

R3and R4each independently from each other represents lower alkyl or cycloalkenyl containing from four to fourteen carbon atoms;

R5represents (1) hydrogen atom, (2) -R9, (3) -R7, (4) -NR7R8, (10)- (CH2)nNR6SO2R9, (14) -CSNR7R8, (15) -SO2R9, (16) -SO2NR7R8, (17) -SO2(CH2)nNR6SO2R9, (18) -SO2NR6(CH2)nR7where n is 1-6, R6and R7each independently of one another denotes hydrogen atom or lower alkyl, R8denotes a hydrogen atom, lower alkyl, cycloalkyl containing from three to fourteen carbon atoms, phenyl or pyridyl, R9refers to (1) allerod, (3) phenethyl, (4) naphthyl, diphenyl, phenyl, unsubstituted or mono-, di - or tizamidine phenyl, the substituents which independently of one another selected from lower alkyl, alkyloxy containing from one to twelve carbon atoms, halogen atom, haloalkyl containing from one to twelve carbon atoms, ceanography, nitro, R7, -NR7R8, -SO2R9, -SO2NR7R8and(CH2)pX, where p = 0, and X denotes haloalkyl containing from one to twelve carbon atoms, (5) heterocyclyl, represents saturated carbocyclic radical containing five or six ring atoms, of which one or two selected from nitrogen, oxygen and sulfur, optionally substituted by one or two substituents selected from lower alkyl, hydroxy, hydroxyalkyl containing from one to twelve carbon atoms, carbonyl group, -R7and-R7or (6) heteroaryl, which represents a monocyclic ring containing one, two or three heteroatoms selected from nitrogen, oxygen, sulfur, or 9-14 membered bicyclic ring system where one ring is in its nature an aromatic, optionally substituted lower alkyl,

<% for p. 1, in which each of R3and R4independently from each other represents lower alkyl or cycloalkyl containing from four to fourteen carbon atoms.

3. Connection on p. 2, in which each of R3and R4independently from each other represents methyl, ethyl, propyl, isopropyl or cyclopropylmethyl.

4. Connection on p. 3, in which R3denotes methyl, and R4denotes ethyl, propyl, isopropyl or cyclopropylmethyl.

5. Connection on p. 4, in which R5means-SO2R9, -COR9, -CONR7R8or- (CH2)nNR6SO2R9.

6. Connection on p. 5, in which R5means-SO2R9.

7. Connection on p. 6, in which R9denotes alkyl containing from one to six carbon atoms.

8. Connection on p. 7, in which R9denotes methyl, ethyl or propyl.

9. Connection on p. 5, in which R5means-COR9.

10. Connection on p. 9, in which R9means heterocyclyl or heteroaryl.

11. Connection on p. 10, in which R9indicates morpholino, piperidinyl or 1,2,3,4-tetrahydro [1,5] naphthyridine.

12. Connection on p. 5, in which R5means-CONR7R8.

14. Connection on p. 13, in which each of R7and R8independently from each other represents methyl, ethyl or propyl.

15. Connection on p. 5, in which R5means- (CH2)nNR6SO2R9.

16. Connection on p. 15, in which n = 1-4, R6denotes a hydrogen atom, and R9denotes alkyl.

17. Connection on p. 16, in which R9denotes methyl, ethyl or propyl.

18. Connection on p. 8, in which R1and R2together with the ring to which they are bound, form a 5 - or 6-membered monocyclic saturated or unsaturated ring, optionally containing 0, 1 or 2 heteroatoms, independently from each other selected from nitrogen atoms, oxygen.

19. Connection on p. 18, in which R1and R2together with the ring to which they are bound, form a 5 - or 6-membered monocyclic saturated ring, optionally containing 0, 1 or 2 heteroatoms of oxygen, and in which the ring is optionally mono - or disubstituted by lower alkyl.

20. Connection on p. 19, in which R1and R2together with the ring to which they are linked, form of indanyl, 2,3-dihydrobenzofuran-5-yl, 2,3-dihydrobenzofuran-6-yl, 3,3-dimethyl-2,3-dihydrofuran-5-yl, 3,3-dimethy which together with the ring, with which they are linked, form a 2,3-dihydrobenzofuranyl, R3denotes methyl, R4denotes ethyl, and R9denotes methyl.

22. Connection on p. 5, in which R1denotes a hydrogen atom, and R2indicates alkyloxy containing from one to twelve carbon atoms, halogen atom or haloalkyl containing from one to twelve carbon atoms.

23. Connection on p. 22, in which R2denotes methoxy, ethoxy, propoxy, chlorine atom or bromine or trifluoromethyl.

24. Connection on p. 5, in which R1denotes a hydrogen atom, and R2refers to-NR7R9.

25. Connection on p. 24, in which R7denotes a hydrogen atom, and R9denotes phenyl, optionally substituted by 1-3 substituents selected from lower alkyl, alkyloxy, haloalkyl, or halogen atom.

26. Connection on p. 25, in which R9denotes phenyl, optionally substituted by 1-3 substituents selected from methyl, ethyl, methoxy, ethoxy, chlorine atom or trifloromethyl.

27. The compound of formula I, selected from the group comprising N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl(1-methanol-phenylpiperidine-4-ylmethyl)amine, N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-propyl (who yl)piperidine-4-ylmethyl]amine, N-[2-(2,3-dihydrobenzofuran-6-yl)-1-methylethyl]-N-cyclopropylmethyl [1-(morpholine-4-carbonyl)piperidine-4-ylmethyl]amine, N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-ethyl[1-(morpholine-4-carbonyl)piperidine-4-ylmethyl]amine, N-[2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl]-N-propyl[1-(morpholine-4-carbonyl) piperidine-4-ylmethyl]amine, N-[2-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-1-methylethyl]-N-ethyl[1-(morpholine-4-carbonyl)piperidine-ylmethyl]amine, (S)-N-[3-{4-[[(2-(2,3-dihydrobenzofuran-5-yl)-1-methylethyl)ethylamino]methyl] piperidine-1-yl}-3-oxopropyl} methanesulfonamide, N-[2-(indan-5-yl)-1-methylethyl]-N-ethyl(1-methanesulfonamido-4-ylmethyl]amine, N-[2-(indan-5-yl)-1-methylethyl]-N-propyl(1-methanesulfonamido-4-ylmethyl]amine, N-[2-(3,3-dimethyl-2,3-dihydrobenzofuran-6-yl)-1-methylethyl]-N-ethyl [1 - (morpholine-4-carbonyl)piperidine-4-ylmethyl]amine, N-[2-(3,3-dimethyl-2,3-dihydrobenzofuran-6-yl)-1-methylethyl]-N-ethyl(1 methanesulfonanilide-4-ylmethyl) amine, N-[2-(4-methoxyphenyl)-1-methylethyl]N-ethyl [1-(dimethylamino-bonyl)piperidine-4-ylmethyl]amine, N-[2-(3-triptoreline)-1-methylethyl]-N-ethyl[1-(dimethylamino-carbonyl)piperidine-4-ylmethyl]amine, N-[2-(3-triptoreline)-1-methylethyl]-N-ethyl[1 - (piperidine-1-carbonyl)piperidine-4-ylmethyl]amine, N-[2-(4-triptoreline)-1-methylethyl]-N-ethyl[1-(piperidine-1-carbonyl) piperidine-4-iriformation)-1-methylethyl]-N-ethyl[1-(morpholine-4-CT-bonyl)piperidine-4-ylmethyl]amine, N-[2-(3-triptoreline)-1-methylethyl]-N-ethyl[1-(1,2,3,4-tetrahed-ro[1,5]naphthiridine-1-carbonyl)piperidine-4-ylmethyl]amine, N-[2-(3-chlorophenyl)-1-methylethyl]-N-ethyl[1-(piperidine-1-carbonyl)piperidine-4-ylmethyl]amine, N-[2-(3-triptoreline)-1-methylethyl]-N-propyl[1-(morpholine-4-carbonyl)piperidine-4-ylmethyl]amine, N-{2-[3-(4-methoxyphenylethylamine)phenyl]-1-methylethyl}-N-propyl [1 - (morpholine-4-carbonyl)piperidine-4-ylmethyl]amine and N-{2-[3-(4-methylphenylethylamine)phenyl]-1-methylethyl}-N-propyl [1 - (morpholine-4-carbonyl)piperidine-4-ylmethyl]amine.

28. Connection on p. 1 or 27, pharmaceutically acceptable salt is a salt formed with hydrochloric acid, phosphoric acid, triperoxonane acid or Dibenzoyl-L-tartaric acid.

29. The drug, which is an antagonist of muscarinic receptor, comprising a compound according to any one of paragraphs.1-28 and pharmaceutically acceptable excipients.

30. Drug for p. 29 for the treatment of urogenital system.

Priority items:

27.02.1998 - PP.3, 6, 7, 8, 9, 18, 29;

19.11.1998 - PP.1, 2, 4, 5, 10, 11-17, 19-28, 30.

 

Same patents:

The invention relates to organic chemistry, namely to new derivatives of benzoperylene

The invention relates to new substituted pyrazolylborate General formula (I) in which R1-R6have the meanings given in the description of the invention

The invention relates to piperazine derivatives of the formula I, in which R1denotes a substituted radicals CN or Hal indole-3-ilen residue, R2denotes unsubstituted 2-oxo-2H-1-benzopyran-6-yl or 2-oxo-2H-1-benzopyran-4-yl

The invention relates to novel azole compounds having antifungal activity, their preparation and application

The invention relates to 1,4-disubstituted the piperazines of General formula I, the method of production thereof, containing compositions and their use for the clinical treatment of painful conditions, increased pain sensitivity and/or inflammatory conditions in which the pathophysiological role of C-fibers, causing neurogenic pain or inflammation
The invention relates to an improved process for the preparation of doxazosin, which is known antihypertensive agent used in hypertension and prostate cancer

The invention relates to amide derivative of the formula I

< / BR>
where R3represents (1-6C)alkyl or halogen; m is 0, 1, 2 or 3; R1represents hydroxy, halogen, trifluoromethyl, nitro, amino, (1-6C)alkyl, (2-6C)alkenyl, (2-6C)quinil, (1-6C)alkoxy, (1-6C)alkylamino, di-[(1-6C)alkyl] amino, amino-(2-6C)alkylamino, (1-6C)alkylamino-(2-6C)alkylamino etc

The invention relates to derivatives of cyclic amines and their use as pharmaceuticals, particularly to a compound represented by the General formula (I), its pharmaceutically acceptable acid additive salts or its pharmaceutically acceptable C1-C6alcaldicios salt, R1-phenyl, C3-8-cycloalkyl, aromatic heterocycle with 1-3 heteroatoms selected from O, S, N, or combinations thereof, and these groups may be condensed with benzene ring or an aromatic heterocyclic group with heteroatoms, selected from O, S or N, or combinations thereof, and may also have different substituents

The invention relates to new salts of pyridinium General formula (I) or their pharmaceutically acceptable salts, where R1is-R4- R5or-N(R7)N(R7R9, R4choose from the group of-N(R7R6O-, N(R7R6N(R7), -OR6O-,

-OR SIG6N(R7)-, where R6- alkyl, R5choose from the group of alkyl, aryl, including heteroaryl, -COR7, -SO2R7and-COR10where R7Is H, alkyl or aryl, including heteroaryl, R2Is F, Cl, Br, J, alkyl, aryl, including heteroaryl, formyl, acyl, C(O)NR7R10or C(O)or SIG7, m = 0, 1, or 2, R3selected from the group comprising R7OR7N(R7)(R10) and CH(R7)C(O)R8, R8is R7OR7and NR7R10, R9is hydrogen, alkyl, aryl, including heteroaryl, -C(O)R10, -SO2R10, -C(S)OTHER10, -C(NH)NH(R10), -C(O)OTHER10, R10- H, alkyl, or aryl, including heteroaryl, and in each case, it is not necessarily different from R7X represents an ion halogen provided that 1) when two alkyl groups are the same carbon or nitrogen, they are not necessarily linked together with the formation of a cyclic structure, and (2) nitrogen heteroaryl ring R1

The invention relates to new N-phenylamine and N-pyridylamine derivative of the formula I

< / BR>
in which X denotes O or S;

R1and R2which may be identical or different, denote hydrogen, (C1-C6)alkyl or (C3-C8)cycloalkyl or R1and R2together with the carbon atom to which they are attached, form a (C3-C8)cycloalkyl;

R3means (C6-C12)aryl, optionally substituted by one or more radicals Y, which may be the same or different;

Y represents halogen;

R4and R5represent hydrogen;

Ar denotes one of the following groups or WITH:

< / BR>
T represents hydrogen or (C1-C6)alkyl;

T3and T4which may be identical or different, denote (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)allylthiourea;

R6and R7each denotes hydrogen or R6and R7together represent a bond;

Z denotes either (I) the divalent group-CHR9- in which the R11-, in which R10and R11together they form a bond that Z represents the group-CH=CH-, or R10and R11that may be the same or different, have the meanings indicated above for R9or (III) a divalent group-CHR12-CHR13-CH2-, in which R12and R13together they form a bond, Z represents-CH=CH-CH2-, or R12and R13that may be the same or different, have the meanings indicated above for R9,

as well as their additive salts with pharmaceutically acceptable acids or bases, and method of production thereof, pharmaceutical compositions and drug manifesting gipolipedimecescoe and antiatherosclerotic action based on them

The invention relates to new derivatives of 1-[(1-substituted-4-piperidinyl)methyl]-4-piperidine F.-ly (I), where Ar is a group of the formula (Ar-1) or (Ar-2), where R1is a halogen, R2represents hydrogen or lower alkyl, R3represents hydrogen, lower alkyl or lower alkanoyl, R4represents hydrogen or lower alkyl, R5and R6are the same or different and represent hydrogen or lower alkyl, n is 1, 2 or 3, And represents a group of formula (a-1), (a-2) or (a-3): -Z-N(Q1)(Q2) (A-1), where Z represents-CO -, - CS-or-SO2-, Q1and Q2are the same or different and represent hydrogen, lower alkyl, cycloalkyl, unsubstituted or substituted phenyl or phenyl(lower alkyl), or Q1and Q2together with the nitrogen atom form a pyrolidine, piperidine, hexahydroazepin, morpholino, thiomorpholine or pieperazinove ring; -CO-R7(A-2), where R7represents hydrogen, lower alkyl, lower alkoxy, lower alkoxycarbonyl, substituted lower alkyl; -(CH2)p-CH(R8)-COR9(A-3), where p has a value 0, 1, 2, 3, 4 5; R8represents hydrogen or lower alkyl; R9is

The invention relates to the field of organic chemistry and relates to compounds of formula (I) and their pharmaceutically acceptable salts and difficult ether derivatives

< / BR>
where Ar represents a phenyl group which may be optionally substituted from 1 to 3 substituents selected from the group consisting of halogen atoms and triptorelin groups having antifungal activity

The invention relates to derivatives of cyclic amines and their use as pharmaceuticals, particularly to a compound represented by the General formula (I), its pharmaceutically acceptable acid additive salts or its pharmaceutically acceptable C1-C6alcaldicios salt, R1-phenyl, C3-8-cycloalkyl, aromatic heterocycle with 1-3 heteroatoms selected from O, S, N, or combinations thereof, and these groups may be condensed with benzene ring or an aromatic heterocyclic group with heteroatoms, selected from O, S or N, or combinations thereof, and may also have different substituents
Up!