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Details for Patent: 3,932,646

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Details for Patent: 3,932,646

Title: Pharmaceutical compositions containing unsymmetrical esters of 1,4-dihydropyridine 3,5-dicarboxylate
Abstract:Pharmaceutical compositions containing unsymmetrical esters of 1,4-dihydropyridine 3,5-dicarboxylate as the active ingredient and methods of using same. The said ingredients are unsymmetrical esters of 1,4-dihydropyridine 3,5-dicarboxylic acid which are substituted at position-4 of the dihydropyridine ring by phenyl or a substituted phenyl moiety. The compositions have cardiovascular activity which makes them useful for effecting coronary vascular dilation and in the treatment of hypertension.
Inventor(s): Meyer; Horst (Wuppertal-Elberfeld, DT), Bossert; Friedrich (Wuppertal-Elberfeld, DT), Vater; Wulf (Opladen, DT), Stoepel; Kurt (Wuppertal-Vohwinkel, DT)
Assignee: Farbenfabriken Bayer AG (DT)
Filing Date:Sep 21, 1973
Application Number:05/399,387
Claims:1. A pharmaceutical composition useful for effecting coronary vascular dilation and for treating hypertension in humans and animals which comprises a coronary vascular dilating amount or an antihypertensive amount of a compound of the formula: ##SPC2##

wherein

R is phenyl, unsubstituted or substituted by a substituent selected from the group consisting of lower alkyl, lower alkoxy, halogeno, trifluoromethyl and carbo(lower alkoxy) or by up to three lower alkoxy or halogeno substituents;

R.sup.1 and R.sup.3, independent of the other, is hydrogen, methyl, ethyl or propyl;

R.sup.2 is a member selected from the group consisting of lower alkyl, allyl, butenyl, propargyl, butynyl and lower alkoxy(lower alkyl);

R.sup.4 is a member different from R.sup.2 and is selected from the group consisting of allyl, butenyl, propargyl, butynyl and lower alkoxy(lower alkyl),

or a pharmaceutically acceptable acid addition salt thereof, in combination with a pharmaceutically acceptable non-toxic inert carrier.

2. A pharmaceutical composition according to claim 1 wherein each of R.sup.1 and R.sup.3 is lower alkyl, R.sup.2 is lower alkyl and R.sup.4 is lower alkenyl, lower alkynyl, or lower alkoxy (lower alkyl).

3. A pharmaceutical composition according to claim 2 wherein R.sup.1 and R.sup.3 are each methyl, R.sup.2 is methyl, ethyl, propyl or isopropyl, R.sup.4 is allyl, propargyl, methoxyethyl or propoxyethyl and R is phenyl substituted by methyl, methoxy, fluoro, chloro, trifluoromethyl or carbo(lower alkoxy).

4. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(2'-methylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester-5-allyl ester.

5. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(2'-methylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester-5-propargyl ester.

6. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(2'-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-allyl ester.

7. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(2'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicar boxylic acid 3-ethyl ester-5-propargyl ester.

8. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(2'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicar boxylic acid 3-ethyl ester-5-allyl ester.

9. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(2'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicar boxylic acid 3-methyl ester-5-propargyl ester.

10. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(2'-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester-5-.beta.-propoxyethyl ester.

11. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(2'-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester-5-allyl ester.

12. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(2,', 3', 4'-trimethoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester-5-allyl ester.

13. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(3', 4'-dimethoxy-5-bromophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-allyl ester.

14. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(2'-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-propargyl ester 5-methyl ester.

15. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(2'-trifluoromethylphenyl)-1,4-dihydropyridine 3,5-dicarboxylic acid 3-propargyl ester 5-methyl ester.

16. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(2'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarbox ylic acid 3-propargyl ester 5-ethyl ester.

17. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(2'-chlorophenyl)-1,4-dihydropyridine 3,5-dicarboxylic acid 3-.beta.-methoxyethyl ester 5-ethyl ester.

18. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(3'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarbox ylic acid 3-isopropyl ester 5-allyl ester.

19. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(2'-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-propargyl ester 5-methyl ester.

20. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(3'-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-allyl ester 5-ethyl ester.

21. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(2'-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-propargyl ester 5-ethyl ester.

22. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(4'-carboxyethylphenyl)-1,4-dihydropyridine-3,5-dicarboxyli c acid 3-propargyl ester 5-ethyl ester.

23. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(2', 4', 5'-trimethoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-allyl ester 5-methyl ester.

24. A method of effecting coronary vascular dilation and treating hypertension in humans and animals which comprises administering to such human or animal a coronary vascular dilating amount or an anti-hypertensive amount of a compound of the formula: ##SPC3##

wherein

R is phenyl, unsubstituted or substituted by a substituent selected from the group consisting of lower alkyl, lower alkoxy, halogeno, trifluoromethyl and carbo(lower alkoxy) or by up to three lower alkoxy or halogeno substituents;

R.sup.1 and R.sup.3, independent of the other, is hydrogen, methyl, ethyl or propyl;

R.sup.2 is a member selected from the group consisting of lower alkyl, allyl, butenyl, propargyl, butynyl and lower alkoxy(lower alkyl);

R.sup.4 is a member different from R.sup.2 and is selected from the group consisting of allyl, butenyl, propargyl, butynyl and lower alkoxy(lower alkyl),

or a pharmaceutically acceptable acid addition salt thereof.

25. A method according to claim 24 wherein R.sup.2 is lower alkyl and R.sup.4 is allyl, propargyl or lower alkoxy(lower alkyl).

26. A method according to claim 24 wherein R.sup.1 and R.sup.3 are each methyl, R.sup.2 is methyl, ethyl, propyl or isopropyl, R.sup.4 is allyl, propargyl, methoxyethyl or propoxyethyl and R is phenyl substituted by methyl, methoxy, fluoro, chloro, trifluoromethyl or carbo(lower alkoxy).

27. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(2'-methylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester-5-allyl ester.

28. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(2'-methylphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester-5-propargyl ester.

29. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(2'-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-allyl ester.

30. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(2'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarbox ylic acid 3-ethyl ester-5-propargyl ester.

31. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(2'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarbox ylic acid 3-ethyl ester-5-allyl ester.

32. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(2'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarbox ylic acid 3-methyl ester-5-propargyl ester.

33. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(2'-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester-5-.beta.-propoxyethyl ester.

34. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(2'-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester-5-allyl ester.

35. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(2', 3', 4'-trimethoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester-5-allyl ester.

36. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(3', 4'-dimethoxy-5-bromophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-allyl ester.

37. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(2'-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-propargyl ester 5-methyl ester.

38. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(2'-trifluoromethylphenyl)-1,4-dihydropyridine 3,5-dicarboxylic acid 3-propargyl ester 5-methyl ester.

39. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(2'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarbox ylic acid 3-propargyl ester 5-ethyl ester.

40. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(2'-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-.beta.-methoxyethyl ester 5-ethyl ester.

41. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(3'-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarbox ylic acid 3-isopropyl ester 5-allyl ester.

42. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(2'-fluorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-propargyl ester 5-methyl ester.

43. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(3'-chlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-allyl ester 5-ethyl ester.

44. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(2'-methoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-propargyl ester 5-ethyl ester.

45. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(4'-carboxyethylphenyl)-1,4-dihydropyridine-3,5-dicarboxyli c acid 3-propargyl ester 5-ethyl ester.

46. A method according to claim 24 wherein the compound is 2,6-dimethyl-4-(2' , 4', 5'-trimethoxyphenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-allyl ester 5-methyl ester.
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