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Claims for Patent: 3,932,645

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Claims for Patent: 3,932,645

Title: Pharmaceutical compositions containing unsymmetrical esters of 1,4-dihydropyridine 3,5-dicarboxylic acid
Abstract:Pharmaceutical compositions containing unsymmetrical esters of 1,4-dihydropyridine 3,5-dicarboxylic acids as the active ingredient and methods of using same. The said ingredients are unsymmetrical 1,4-dihydropyridine 3,5-dicarboxylates which are substituted at position-4 of the dihydropyridine nucleus by phenyl which contains at least one nitro, cyano, azido, alkylthio, or alkylsulphonyl substituent. The compositions have a cardiovascular activity which makes them useful for effecting coronary vascular dilation and, also, they have utility 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)
Application Number:05/398,982
Patent Claims: 1. A pharmaceutical composition useful for effecting coronary vascular dilation and for treating hypertension which comprises a coronary vascular dilating effective amount or an antihypertensive amount of a compound of the formula: ##SPC2##

wherein

R is mono or disubstituted phenyl in which the substituents are selected from the group consisting of nitro, cyano, azido, --S(O).sub.n -lower alkyl in which n has a value of 0, 1 or 2, lower alkyl, lower alkoxy and halogeno, at least one of said substituents being nitro, cyano, azido or --S(O).sub.n -lower alkyl; or a member selected from the group consisting of naphthyl, pyridyl, methylpyridyl, thenyl, furyl, and pyrryl;

each of R.sup.1 and R.sup.3, independent of the other, is hydrogen or lower alkyl;

R.sup.2 is lower alkyl, lower alkenyl, lower alkynyl, or lower alkoxy(lower alkyl);

R.sup.4 is lower alkyl, lower alkenyl, lower alkynyl, or lower alkoxy(lower alkyl), R.sup.4 being different from R.sup.2,

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 and R.sup.2 is lower alkyl.

3. A pharmaceutical composition according to claim 1 wherein R.sup.1 and R.sup.3 are each methyl, R.sup.2 is methyl, ethyl, propyl or isopropyl and R.sup.4 is different from R.sup.2 and is methyl, ethyl, propyl, isopropyl, allyl, propargyl, propoxyethyl, methoxyethyl or cyclohexyl.

4. A pharmaceutical composition according to claim 3 wherein R is phenyl substituted by cyano, nitro or methylmercapto and further unsubstituted or substituted by chloro.

5. A pharmaceutical composition according to claim 3 wherein R is pyridyl, pyrryl, furyl, or pyrimidyl.

6. A pharmaceutical composition according to claim 3 wherein R is naphthyl, quinolyl or isoquinolyl.

7. A pharmaceutical composition according to claim 1 in oral administration form.

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

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

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

11. A pharmaceutical composition according to claim 1 wherein the compound is 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine 3-.beta.-methoxyethyl ester-5-isopropyl ester.

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

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

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

15. A method of effecting coronary vascular dilation in humans and animals which comprises administering to such human or animal an amount of a compound of the formula: ##SPC3##

wherein

R is mono or disubstituted phenyl in which the substituents are selected from the group consisting of nitro, cyano, azido, --S(O).sub.n -lower alkyl in which n has a value of 0, 1 or 2, lower alkyl, lower alkoxy and halogeno, at least one of said substituents being nitro, cyano, azido or --S(O).sub.n -lower alkyl; or a member selected from the group consisting of naphthyl, pyridyl, methylpyridyl, thenyl, furyl, and pyrryl;

each of R.sup.1 and R.sup.3, independent of the other, is hydrogen or lower alkyl;

R.sup.2 is lower alkyl, lower alkenyl, lower alkynyl, or lower alkoxy(lower alkyl);

R.sup.4 is lower alkyl, lower alkenyl, lower alkynyl, or lower alkoxy(lower alkyl), R.sup.4 being different from R.sup.2,

or a pharmaceutically acceptable acid addition salt thereof, sufficient to effect coronary vascular dilation.

16. A method according to claim 15 wherein each of R.sup.1 and R.sup.3 is lower alkyl and R.sup.2 is lower alkyl.

17. A method according to claim 15 wherein R.sup.1 and R.sup.3 are each methyl, R.sup.2 is methyl, ethyl, propyl or isopropyl and R.sup.4 is different from R.sup.2 and is methyl, ethyl, propyl, isopropyl, allyl, propargyl, propoxyethyl, methoxyethyl or cyclohexyl.

18. A method according to claim 15 wherein R is phenyl substituted by cyano, nitro or methylmercapto and further unsubstituted or substituted by chloro.

19. A method according to claim 15 wherein R is pyridyl, pyrryl or furyl.

20. A method according to claim 15 wherein R is naphthyl.

21. A method according to claim 15 wherein the administration is oral.

22. The method according to claim 15 wherein the compound is 2,6-dimethyl-4-(2'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-isopropyl ester.

23. The method according to claim 15 wherein the compound is 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-ethyl ester.

24. The method according to claim 15 wherein the compound is 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-isopropyl ester.

25. The method according to claim 15 wherein the compound is 2,6-dimethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine 3-.beta.-methoxyethyl ester-5-isopropyl ester.

26. The method according to claim 15 wherein the compound is 2,6-dimethyl-4-(4'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-ethyl ester.

27. The method according to claim 15 wherein the compound is 2,6-dimethyl-4-(.alpha.-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-isopropyl ester.

28. The method according to claim 15 wherein the compound is 2,6-dimethyl-4-(.alpha.-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-methyl ester-5-propargyl ester.
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