Derivatives of amines

 

The invention relates to new derivatives of amine of the formula (I), where R1is karbamoilnuyu group (which may have one or two Deputydescribed later), thiocarbamoyl group (which may have one or two Deputydescribed later), sulfonyloxy group (which has one Deputydescribed next) or carbonyl group (which has one Deputydescribed below); R2represents a hydrogen atom; R3represents C1-C10alkyl group; W1, W2and W3each represents a single bond or C1-C8alkylenes group; X represents an oxygen atom or a sulfur atom; Y represents an oxygen atom; Q represents a sulfur atom; Z represents = CH-group or a nitrogen atom; Ar represents a benzene or naphthalene ring; L represents 1 to 2 substituents in Ar ring and each Deputy represents a hydrogen atom, a C1-C6alkyl group; Deputyrepresents (i) C1-C10alkyl group, (ii)3-C10cycloalkyl group, (iii) phenyl group (//img.russianpatents.com/chr/947.gif">represents (i) C1-C6alkyl group, (ii) C1-C6halogenating group, (iii) C1-C6CNS group, (iv) halogen atom, (v) hydroxyl group, (vi) cyano, (vii) a nitro-group, (viii) alkylenedioxy; or its pharmaceutically acceptable salts or esters. Pharmaceutical composition having PPAR-trigger action, including the compound of formula (I) or its pharmaceutically acceptable salt, or ester derivative in an effective amount with a carrier or diluent. Agent containing the compound of formula (I) or its pharmaceutically acceptable salt, or ester derivative, suitable for prevention or treatment of cancer. Method of drug effects on the body of a warm-blooded animal for the treatment or prevention of cancer, including the introduction in need of such treatment a warm-blooded animal an effective amount of the compounds of formula (I) or its pharmaceutically acceptable salt, or ester derivative. The method of treatment or prophylaxis of cancer in a warm-blooded animal, including the introduction of a warm-blooded animal requiring such treatment, an effective amount of a compound Faure. The technical result - obtaining new amine derivatives having PPAR-trigger action. 5 C. and 31 C.p. f-crystals, 7 PL.

Description text in facsimile form (see graphic part)and

Claims

1. Derived amine of the formula (I)

where R1is karbamoilnuyu group (which may have one or two Deputydescribed later), thiocarbamoyl group (which may have one or two Deputydescribed later), sulfonyloxy group (which has one Deputydescribed next) or carbonyl group (which has one Deputydescribed below);

R2represents a hydrogen atom;

R3represents C1-C10alkyl group;

W1, W2and W3each represents a single bond or C1-C8alkylenes group;

X represents an oxygen atom or a sulfur atom;

Y represents an oxygen atom;

Q represents a sulfur atom;

Z represents =CH - group is in her AG ring and each Deputy represents a hydrogen atom, C1-6alkyl group;

Deputyrepresents (i) C1-C10alkyl group, (ii)3-C10cycloalkyl group, (iii) phenyl group (which may have from 1 to 3 substituentsdescribed below), (iv) benzyl group (which may have 1 Deputydescribed later, on the phenyl portion), (v) pyridyloxy group or (vi) phenylsulfonyl group;

Deputyrepresents (i) C1-C6alkyl group, (ii) C1-C6halogenating group, (iii) C1-C6CNS group, (iv) halogen atom, (v) hydroxyl group, (vi) cyano, (vii) a nitro-group, (viii) C1-C4alkylenedioxy,

or its pharmacologically acceptable salt or ester.

2. Derived amine or its pharmacologically acceptable salt p. 1, where R1is karbamoilnuyu group (which may have one Deputy), thiocarbamoyl group (which may have one Deputy), sulfonyloxy group (which has one Deputy) or carbonyl group (which has one ub>1is karbamoilnuyu group (which has one Deputy).

4. Derived amine or its pharmacologically acceptable salt p. 1, where R1represents a carbonyl group (which has one Deputy).

5. Derived amine or its pharmacologically acceptable salt according to any one of paragraphs.1-4, where R3represents C1-C6alkyl group.

6. Derived amine or its pharmacologically acceptable salt according to any one of paragraphs.1-4, where R3represents C1-C4alkyl group.

7. Derived amine or its pharmacologically acceptable salt according to any one of paragraphs.1-4, where R3represents C1-C2alkyl group.

8. Derived amine or its pharmacologically acceptable salt according to any one of paragraphs.1-7, where W1, W2and W3each represents a single bond or C1-C4alkylenes group.

9. Derived amine or its pharmacologically acceptable salt according to any one of paragraphs.1-7, where W1and W2each represents a single bond or C1-C4alkylenes group, and W3represents C1-C2alkylenes group.

10. Derived amine or farmacol the sub>1-C2alkylenes group, and W3represents a methylene group.

11. Derived amine or its pharmacologically acceptable salt according to any one of paragraphs.1-10, where X represents the oxygen atom.

12. Derived amine or its pharmacologically acceptable salt according to any one of paragraphs.1-11, where Z is =CH - group.

13. Derived amine or its pharmacologically acceptable salt according to any one of paragraphs.1-11, where Z represents a nitrogen atom.

14. Derived amine or its pharmacologically acceptable salt according to any one of paragraphs.1-13, where AG represents a naphthalene ring.

15. Derived amine or its pharmacologically acceptable salt according to any one of paragraphs.1-13, where AG represents a benzene ring.

16. Derived amine or its pharmacologically acceptable salt according to any one of paragraphs.1-15, where L represents a hydrogen atom.

17. Derived amine or its pharmacologically acceptable salt according to any one of paragraphs.1-16, where Deputyrepresents (i) C1-C8alkyl group, (ii)5-C10cycloalkyl group, (iii) phenyl group (which may have from 1 to 3 substituents), (iv) benzyl group (which may have one Deputyin the phenyl is logicheskie acceptable salt according to any one of paragraphs.1-16, where Deputyrepresents (i) C1-C4alkyl group, (ii)5-C10cycloalkyl group, (iii) phenyl group (which may have from 1 to 3 substituents), (iv) benzyl group (which may have one Deputyin the phenyl part), or (v) pyridyloxy group.

19. Derived amine or its pharmacologically acceptable salt according to any one of paragraphs.1-16, where Deputyrepresents a phenyl group (which may have from 1 to 3 substituents).

20. Derived amine or its pharmacologically acceptable salt according to any one of paragraphs.1-19, where Deputyrepresents (i) C1-C6alkyl group, (ii) C1-C2halogenating group, (iii) C1-C4CNS group, (iv) halogen atom, (v) hydroxyl group, (vi) cyano, (vii) a nitro-group, (viii) C1-C4alkylenedioxy group.

21. Derived amine or its pharmacologically acceptable salt according to any one of paragraphs.1-19, where Deputyrepresents (i) C1-C6alkyl group, (ii) triptorelin group, (iii) C1-C4alkoxylalkyl.

22. Derived amine or its pharmacologically acceptable salt according to any one of paragraphs.1-19, where Deputyrepresents (i) C1-C4alkyl group, (ii) triptorelin group, (iii) halogen atom, or (iv) the nitrogroup.

23. Derived amine or its pharmacologically acceptable salt p. 1, where R3represents C1-C6alkyl group;

W1, W2and W3each represents a single bond or C1-C4alkylenes group;

Z represents =CH - group;

AG represents a benzene ring;

Deputyrepresents (i) C1-C8alkyl group, (ii)5-C10cycloalkyl group, (iii) phenyl group (which may have from 1 to 3 substituents), (iv) benzyl group (which may have one Deputyin the phenyl part), (v) pyridyloxy group, (vi) phenylsulfonyl group;

Deputyrepresents (i) C1-C6alkyl group, (ii) C1-C4halogenating group, (iii) C1-C6CNS group, (iv) halogen atom, (v) hydroxyl group, (vi) cyano, (vii) a nitro-group, (viii) C1-C4alkyl is made karbamoilnuyu group (which may have one Deputy), thiocarbamoyl group (which may have one Deputy), sulfonyloxy group (which has one Deputy) or carbonyl group (which has one Deputy);

R3represents C1-C4alkyl group;

W1and W2each represents a single bond or C1-C4alkylenes group and W3represents C1-C2alkylenes group;

Z represents =CH - group;

AG represents a benzene ring;

L represents from 1 to 2 substituents ar ring and each Deputy represents a hydrogen atom, a C1-C4alkyl group;

Deputyrepresents (i) C1-C8alkyl group, (ii) C5-C10cycloalkyl group, (iii) phenyl group (which may have from 1 to 3 substituents), (iv) benzyl group (which may have one Deputyon the phenyl portion), (v) pyridyloxy group or (vi) phenylsulfonyl group (which may have from 1 to 3 substituents (phenyl);

Deputyrepresents (i) C1- 1-C4alkylenedioxy.

25. Derived amine or its pharmacologically acceptable salt p. 1, where R1is karbamoilnuyu group (which has one Deputy), thiocarbamoyl group (which has one Deputy), sulfonyloxy group (which has one Deputy).

26. Derived amine under item 1:

1-(4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl)-3-atilmotin,

1-(adamant-1-yl)-3-(4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl)urea,

1-(4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl) phenoxymethyl]-1-methyl-1H-benzimidazole-6-yloxy] phenyl)-3-phenylacetone,

1-(2,4-differenl)-3-[2-(4-[2-[4-(2,4-dioxo-thiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazole-6-yloxy]-phenyl)ethyl]urea,

1-(4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]-2,6-dimetilfenil)-3-(4-nitrophenyl)urea,

1-(4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl-1-n-hexyl-3-(4-forfinal)urea,

1-(2,6-diisopropyl,

1-benzyl-3-(7-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)-phenoxymethyl]-1-methyl-1H-benzimidazole-6-yloxy]naphthalene-yl)urea,

1-(4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl)-3-(cyclo-hexyl)thiourea,

1-benzyl-3-(7-[2-[4-(2,4-dioxothiazolidine-5~ylmethyl)-phenoxymethyl]-1-methyl-1H-benzimidazole-6-yloxy]naphthalene-yl)thiourea,

1-(4-chlorophenyl)-3-(4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)-phenoxymethyl]-1-methyl-1H-benzimidazole-6-yloxy]-2,6-dimetilfenil)thiourea,

N-(4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl)methane-sulfonamide,

1-(3-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl)-3-phenyl-urea,

1-(3-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl)-3-[2-(trifluoromethyl)-phenyl]urea,

1-(3-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl)-3-[4-(trifluoromethyl)-phenyl]urea,

1-(3-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl)-3-(4-forfinal)urea,

1-(3-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl)-3-[4-(trifluoromethyl)benzyl]urea,

N-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl]-N-n-exilerated,

amide N-[4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl]cyclopentanecarboxylic acid,

N-[4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl]benzamide,

amide N-[4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl] naphthalene-2-carboxylic acid,

2,4-debtor-N-[4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl]benzamide,

3-chloro-N-[4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxymethyl] -1-methyl-1 H-benzimidazole-6-yloxy]phenyl] benzamide,

N-[4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl]nicotinamide,

N-[4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl) phenoxymethyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl] isonicotinamide,

3,5-di-tert-butyl-N-[2-(4-[2-[4-(2,4-Dioxothiazolidine-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazole-6-yloxy]-phenyl)ethyl]-4-hydroxybenzamide,

2-(3-chlorophenyl)-N-[2-[4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazole-6-yloxy]-phenyl]ethyl|ndimethylacetamide and

N-[2-[4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl]ethyl] nicotinamide or their pharmacologically acceptable salts under item 1.

1-(adamant-1-yl)-3-(4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazole-6-yloxy]-phenyl)urea,

1-(2,4-differenl)-3-[2-(4-[2-[4-(2,4-dioxo-thiazolidin-5-ylmethyl)phenoxymethyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl)ethyl] urea,

1-benzyl-3-(7-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)-phenoxymethyl]-1-methyl-1H-benzimidazole-6-yloxy]naphthalene-1-yl)urea,

1-(4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl)-3-(cyclohexyl)thiourea,

N-(4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl)methane-sulfonamide,

1-(3-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl)-3-phenylacetone,

1-(3-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl)-3-[2-(trifluoromethyl)phenyl]urea,

1-(3-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl)-3-[4-(trifluoromethyl)phenyl]urea,

1-(3-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl)-3-(4-forfinal)urea,

N-[4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl]acetamide", she

amide N-[4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl]benzamide,

2,4-debtor-N-[4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl) phenoxymethyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl]-benzamide,

N-[4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl]nicotinamide,

N-[4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl] isonicotinamide and

N-[2-[4-[2-[4-(2,4-dioxothiazolidine-5-ylmethyl)phenoxy-methyl]-1-methyl-1H-benzimidazole-6-yloxy]phenyl]ethyl] nicotinamide

or their pharmacologically acceptable salts.

28. Pharmaceutical composition having PPAR-trigger action that includes a pharmacologically active compound together with a carrier or diluent, characterized in that the pharmacologically active compound is a compound according to any one of paragraphs.1-27, or its pharmaceutically acceptable salt, or ester derivative in an effective amount.

29. The compound according to any one of paragraphs.1-27 or its pharmaceutically acceptable salt with PPARy-trigger action.

30. The compound according to any one of paragraphs.1-27 as an active ingredient in pharmaceutical compositions for prevention or treatment of cancer.

31. Agent containing the compound according to any one of paragraphs.1-27, or its farmace the Way medicinal effects on the body of a warm-blooded animal for the treatment or prevention of cancer, including the introduction in need of such treatment a warm-blooded animal an effective amount of a compound according to any one of paragraphs.1-27, or its pharmaceutically acceptable salt, or ester derivative.

33. The pharmaceutical composition according to p. 28, characterized in that it further includes RXR activator.

34. The compound according to any one of paragraphs.1-27, or its pharmaceutically acceptable salt, or ester derivative in combination with RXR activators as an active ingredient in pharmaceutical compositions for prevention or treatment of cancer.

35. Agent p. 31, characterized in that it further comprises RXR activator suitable for prevention or treatment of cancer.

36. The method of treatment or prophylaxis of cancer in a warm-blooded animal, including the introduction of a warm-blooded animal requiring such treatment, an effective amount of a compound according to any one of paragraphs.1-27, or its pharmaceutically acceptable salt, or ester derivative in combination with RXR activator.

 

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