Derivatives of quinoline, the retrieval method (variants), pharmaceutical composition and method of treatment using them

 

Describes quinoline derivatives of General formula (I), where R is chosen from methyl, ethyl, n-propyl, isopropyl, n-butyl, R' are selected from methyl, methoxy, fluorine, chlorine, bromine, trifloromethyl and coxFywhere x=0-2, y=1-3 with the proviso that x+y =3, R" is selected from hydrogen, fluorine or chlorine, provided that R" is fluorine or chlorine, only when R' is selected from fluorine and chlorine,4selected from hydrogen or a pharmaceutically acceptable inorganic or organic cations; R5selected from ethyl, n-propyl, isopropyl, methoxy, ethoxy, chlorine, bromine, trifloromethyl, coxFyor och2CHxFywhere x=0 -2, y=1-3 with the proviso that x+y=3, R6is hydrogen, and R5and R6together represent methylenedioxy, as well as any tautomer. Also described pharmaceutical composition having protivotumanki and anti-inflammatory action, containing the compound of General formula (I) together with a pharmaceutically acceptable carrier, methods of making compounds of formula (I), and a method of treating mammals suffering from diseases, the cause of which is autoimmunity and pathological inflammation, the introduction of the specified mammal Saedinenie and anti-inflammatory effect. 5 C. and 38 C.p. f-crystals, 2 PL.

Description text in facsimile form (see graphic part).

Claims

1. The compound of General formula Iwhere R is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl; R is chosen from methyl, methoxy, fluorine, chlorine, bromine, trifloromethyl and coxFywhere x=0-2, y=1-3 with the proviso that x+y=3; R" is selected from hydrogen, fluorine and chlorine, with the proviso that R" is selected from fluorine and chlorine only when R' is selected from fluorine and chlorine; R4selected from hydrogen and pharmaceutically acceptable inorganic and organic cations; R5selected from ethyl, n-propyl, isopropyl, methoxy, ethoxy, chlorine, bromine, trifloromethyl, coxFyand co2CHxFywhere x=0-2, y=1-3, provided that x+y=3; R6is hydrogen; or
R5and R6together represent methylenedioxy;
and any tautomer.

2. Connection on p. 1, in which the pharmaceutically acceptable inorganic cation selected from the cations of sodium, potassium and calcium, and organic cation selected from cations of monoethanolamine, diethanolamine, dimethylaminomethyl.

4. Connection under item 1 or 2, in which R5and R6together represent methylenedioxy.

5. The compound according to any one of the preceding paragraphs, in which R is chosen from methyl and ethyl.

6. The compound according to any one of the preceding paragraphs, in which R' are selected from methoxy, fluorine, chlorine and trifloromethyl, when R" is hydrogen.

7. The compound according to any one of the preceding paragraphs, in which R" is chosen from meta - and parafora provided that R' is orthopteron.

8. Connection under item 1 or 2, representing N-ethyl-N-(3-forfinal)-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoindole-3-carboxamide.

9. Connection under item 1 or 2, representing the N-methyl-N-(2,4-differenl)-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoindole-3-carboxamide.

10. Connection under item 1 or 2, representing the N-methyl-N- (2,5-differenl)-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoindole-3-carboxamide.

11. Connection under item 1 or 2, representing N-ethyl-N-(3-methoxyphenyl)-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxoindole-3-carboxamide.

12. Connection under item 1 or 2, representing the N-methyl-N-(2,5-differenl)-1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxoindole-3-carboxamide.

13. Connection under item 1 or 2, depict the.

14. Connection under item 1 or 2, representing the N-methyl-N-(2,4-differenl)-1,2-dihydro-4-hydroxy-5,6-methylenedioxy-1-methyl-2-oxoindole-3-carboxamide.

15. The compound according to any one of the preceding paragraphs, intended for use in the treatment of diseases caused by autoimmunity.

16. Pharmaceutical composition having protivotumanki and anti-inflammatory action, containing as active ingredient a compound of General formula I and pharmaceutically suitable carrier.

17. The pharmaceutical composition according to p. 16 intended for use as a drug with a daily dose of the active substance from 0.0005 to about 10 mg/kg of body weight.

18. The method of obtaining compounds of General formula I, as described in paragraph 1, which consists in the interaction of hard-ether derivative of quinoline-carboxylic acid of the formula II

where R4, R5and R6have the meanings stated above, with the aniline of the formula III

where R, R' and R" have the meanings specified above, in a suitable solvent, such as toluene, xylene or the like.

19. The method of obtaining compounds of General formula I/img.russianpatents.com/img_data/65/650890.gif">
where R4, R5and R6have the meanings stated above, with the aniline of the formula III

where R, R' and R" have the meanings specified above, using a suitable binding agent, preferably a carbodiimide or thionyl chloride, in the presence of triethylamine and a suitable solvent, for example dichloromethane.

20. A method of treating mammals suffering from pathological inflammation and autoimmunity, providing for the introduction to such mammal compounds of General formula I

where R is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl;
R' is chosen from methyl, methoxy, fluorine, chlorine, bromine, trifloromethyl and coxFywhere x=0-2, y=1-3, provided that x+y=3;
R" is selected from hydrogen, fluorine and chlorine, provided that R" is selected from fluorine and chlorine only when R' is selected from fluorine and chlorine;
R4selected from hydrogen and pharmaceutically acceptable inorganic and organic cations;
R5selected from ethyl, n-propyl, isopropyl, methoxy, ethoxy, chlorine, bromine, trifloromethyl, coxFyand OCH2CHxFywhere x=0-2, y=1-3, provided that x+y=3;
R6is

21. The method according to p. 20, in which the pharmaceutically acceptable inorganic cation selected from cations of sodium, potassium and calcium, and organic cation selected from cations of monoethanolamine, diethanolamine, dimethylaminoethanol, research.

22. The method according to p. 20 or 21, in which R5selected from ethyl, methoxy, chlorine and trifloromethyl.

23. The method according to p. 20 or 21, in which R5and R6together represent methylenedioxy.

24. The method according to p. 20 or 21, in which R is chosen from methyl and ethyl.

25. The method according to p. 20 or 21, in which R' are selected from methoxy, fluorine, chlorine and trifloromethyl, when R" is hydrogen.

26. The method according to p. 20 or 21, in which R" is chosen from meta - and paratore, provided that R' is orthopteron.

27. The method according to p. 20 or 21 in which the compound of General formula I is N-ethyl-N-(3-forfinal)-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoindole-3-carboxamide.

28. The method according to p. 20 or 21 in which the compound of General formula I is N-methyl-N-(2,4-differenl)-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxoindole-3-carboxamide.

29. The method according to p. 20 or 21 in which the compound of General formula I is N-methyl-N-(2,5-differenl)-1,2-dihydro-4-hydroxy-5-chloro-1-methyl-2-oxopentanenitrile)-1,2-dihydro-4-hydroxy-5-ethyl-1-methyl-2-oxoindole-3-carboxamide.

31. The method according to p. 20 or 21 in which the compound of General formula I is N-methyl-N-(2,5-differenl)-1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxoindole-3-carboxamide.

32. The method according to p. 20 or 21 in which the compound of General formula I is N-methyl-N-(4-triptoreline)-1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxoindole-3-carboxamide.

33. The method according to p. 20 or 21 in which the compound of General formula I is N-methyl-N-(2,4-differenl)-1,2-dihydro-4-hydroxy-5,6-methylenedioxy-1-methyl-2-oxoindole-3-carboxamide.

34. The method according to any of paragraphs.20-33 for the treatment of mammals, patients with multiple sclerosis (PC).

35. The method according to any of paragraphs.20-33 for the treatment of mammals, patients with insulin-dependent diabetes mellitus (IDDM).

36. The method according to any of paragraphs.20-33 for the treatment of mammalian patients with systemic lupus erythematosus (SLE).

37. The method according to any of paragraphs.20-33 for the treatment of mammals suffering from rheumatoid arthritis (PA).

38. The method according to any of paragraphs.20-33 for the treatment of mammals suffering from inflammatory bowel disease (IBD).

39. The method according to any of paragraphs.20-33 for the treatment of mammals suffering from psoriasis.

40. The method according to any of paragraphs.20-33 for the treatment of mammalian patients waspa the surrounding, patients with atherosclerosis.

42. The method according to any of paragraphs.20-33 for the treatment of mammals suffering from paralysis.

43. The method according to any of paragraphs.20-33 for the treatment of mammals suffering from Alzheimer's disease.

 

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