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Claims for Patent: 4,264,611

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Claims for Patent: 4,264,611

Title: 2,6-Dimethyl-4-2,3-disubstituted phenyl-1,4-dihydro-pyridine-3,5-dicarboxylic acid-3,5-asymmetric diesters having hypotensive properties, as well as method for treating hypertensive conditions and pharmaceutical preparations containing same
Abstract:The present invention relates to new compounds having antihypertensive effect, which compounds are of the formula I, ##STR1## wherein R.sup.1 is selected from the group consisting of --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 OCH.sub.3, and --CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, and R.sup.2 is selected from the group consisting of --C.sub.2 H.sub.5, --CH(CH.sub.3).sub.2, --C(CH.sub.3).sub.3, --CH(CH.sub.3)CH.sub.2 OCH.sub.3, C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3, and --CH.sub.2 C(CH.sub.3).dbd.CH.sub.2, whereby R.sup.1 and R.sup.2 are not the same, R.sup.3 is selected from the group consisting of chloro, and R.sup.4 is selected from the group consisting of chloro, and methyl, a method for lowering the blood pressure in mammals including man using said compounds, and pharmaceutical preparations containing said compounds.
Inventor(s): Berntsson; Peder B. (Molndal, SE), Carlsson; Stig A. I. (Molnlycke, SE), Gaarder; Jan O. (Goteborg, SE), Ljung; Bengt R. (Goteborg, SE)
Assignee: Aktiebolaget Hassle (Molndal, SE)
Application Number:06/050,083
Patent Claims: 1. A compound of the formula I ##STR13## wherein R.sup.1 is selected from the group consisting of --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 OCH.sub.3, and --CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, R.sup.2 is selected from the group consisting of --CH.sub.2 CH.sub.3, --CH(CH.sub.3).sub.2, --C(CH.sub.3).sub.3, --CH(CH.sub.3)CH.sub.2 OCH.sub.3, --C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3, and --CH.sub.2 C(CH.sub.3).dbd.CH.sub.2, whereby R.sup.1 and R.sup.2 are not the same, R.sup.3 is chloro and R.sup.4 is selected from the group consisting of chloro, and methyl.

2. A compound of claim 1, wherein R.sup.1 is selected from the group consisting of --CH.sub.3, --CH.sub.2 CH.sub.2 OCH.sub.3, and --CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, and R.sup.2 is selected from the group consisting of --C.sub.2 H.sub.5, --CH(CH.sub.3).sub.2, --C(CH.sub.3).sub.3, --CH(CH.sub.3)CH.sub.2 OCH.sub.3, and C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3, R.sup.3 is chloro, and R.sup.4 is selected from the group consisting of chloro, and methyl.

3. A compound of claim 1, wherein R.sup.1 is --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 OCH.sub.3, and --CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, R.sup.2 is --CH.sub.2 C(CH.sub.3).dbd.CH.sub.2, R.sup.3 is chloro, and R.sup.4 is selected from the group consisting of chloro, and methyl.

4. A method for treating arterial hypertension in a mammal suffering therefrom, comprising administering to said mammal an amount effective to relax the vascular smooth muscle of said mammal of a compound of formula I ##STR14## wherein R.sup.1 is selected from the group consisting of --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 OCH.sub.3, and --CH.sub.2 CH.sub.2 OCH.sub.2 H.sub.5, R.sup.2 is selected from the group consisting of --CH.sub.2 CH.sub.3, --CH(CH.sub.3).sub.2, --C(CH.sub.3).sub.3, --CH(CH.sub.3)CH.sub.2 OCH.sub.3, --C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3, and --CH.sub.2 C(CH.sub.3).dbd.CH.sub.2, whereby R.sup.1 and R.sup.2 are not the same, R.sup.3 is chloro, and R.sup.4 is selected from the group consisting of chloro, and methyl.

5. A method according to claim 4, wherein a compound of formula I is administered, wherein R.sup.1 is selected from the group consisting of --CH.sub.3, --CH.sub.2 CH.sub.2 OCH.sub.3, and --CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, and R.sup.2 is selected from the group consisting of --C.sub.2 H.sub.5, --CH(CH.sub.3).sub.2, --C(CH.sub.3).sub.3, --CH(CH.sub.3)CH.sub.2 OCH.sub.3, and C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3, R.sup.3 is chloro and R.sup.4 is selected from the group consisting of chloro, and methyl.

6. A method according to claim 4, wherein a compound of formula I is administered, wherein R.sup.1 is --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 OCH.sub.3, and --CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, R.sup.2 is selected from the group consisting of --CH.sub.2 C.tbd.CH, --CH.sub.2 C(CH.sub.3).dbd.CH.sub.2, R.sup.3 is chloro and methoxy, and R.sup.4 is selected from the group consisting of chloro, and methyl.

7. Pharmaceutical preparation, which comprises as an active ingredient a therapeutically effective dose of an antihypertensive compound having vascular smooth muscle relaxing properties which compound has the formula I ##STR15## wherein R.sup.1 is selected from the group consisting of --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 OCH.sub.3, and --CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, R.sup.2 is selected from the group consisting of --CH.sub.2 CH.sub.3, --CH(CH.sub.3).sub.2, --C(CH.sub.3).sub.3, --CH(CH.sub.3)CH.sub.2 OCH.sub.3, --C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3, and --CH.sub.2 C(CH.sub.3).dbd.CH.sub.2, whereby R.sup.1 and R.sup.2 are not the same, R.sup.3 is chloro, and R.sup.4 is selected from the group consisting of chloro, and methyl, in association with a pharmaceutically acceptable carrier.

8. A pharmaceutical preparation according to claim 7, wherein the active ingredient is a compound of formula I, wherein R.sup.1 is selected from the group consisting of --CH.sub.3, --CH.sub.2 CH.sub.2 OCH.sub.3, and --CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, and R.sup.2 is selected from the group consisting of --C.sub.2 H.sub.5, --CH(CH.sub.3).sub.2, --C(CH.sub.3).sub.3, --CH(CH.sub.3)C.sub.2 H.sub.5, --CH(CH.sub.3)CH.sub.2 OCH.sub.3, and C(CH.sub.3).sub.2 CH.sub.2 OCH.sub.3, R.sup.3 is chloro and R.sup.4 is selected from the group consisting of chloro and methyl.

9. A pharmaceutical preparation according to claim 7, wherein the active ingredient is a compound of formula I, wherein R.sup.1 is --CH.sub.3, --C.sub.2 H.sub.5, --CH.sub.2 CH.sub.2 OCH.sub.3, and --CH.sub.2 CH.sub.2 OC.sub.2 H.sub.5, R.sup.2 is selected from the group consisting of --CH.sub.2 C(CH.sub.3).dbd.CH.sub.2, R.sup.3 is chloro, and R.sup.4 is selected from the group consisting of chloro, and methyl.

10. A pharmaceutical preparation according to claim 7, wherein the substituted 2,6-dimethyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylic acid-diester compound comprises 0.1 to 99% by weight of the preparation.

11. The compound according to claim 1 which is 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-methylester-5-ethylester.

12. The compound according to claim 1 which is 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-ethylester-5-(2-methoxyethylester).

13. The compound according to claim 1 which is 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-methylester-5-isopropylester.

14. The compound according to claim 1 which is 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-methyl-5-tert.butylester.

15. The compound according to claim 1 which is 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-methylester-5-(2-methoxy-1-methylethylester).

16. The compound according to claim 1 which is 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-(2-methoxyethyl)ester-5-isopropylester.

17. The compound according to claim 1 which is 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-(2-ethoxyethyl)ester-5-ethylester.

18. The compound according to claim 1 which is 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-methylester-5-(2-methoxy-1,1-dimethylethyl)ester.

19. The compound according to claim 1 which is 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-(2-methoxy)ethylester-5-propargyl ester.

20. The compound according to claim 1 which is 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-methylester-5-(2-methyl)allylester.

21. A pharmaceutical preparation according to claim 7 wherein said active ingredient is the compound 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-methylester-5-ethylester.

22. A pharmaceutical preparation according to claim 7 wherein said active ingredient is the compound 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-ethylester-5-(2-methoxyethylester).

23. A pharmaceutical preparation according to claim 7 wherein said active ingredient is the compound 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-methylester-5-isopropylester.

24. A pharmaceutical preparation according to claim 7 wherein said active ingredient is the compound 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-methyl-5-tert.butylester.

25. A pharmaceutical preparation according to claim 7 wherein said active ingredient is the compound 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-methylester-5-(2-methoxy-1-methylethylester).

26. A pharmaceutical preparation according to claim 7 wherein said active ingredient is the compound 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-(2-methoxyethyl)ester-5-isopropylester.

27. A pharmaceutical preparation according to claim 7 wherein said active ingredient is the compound 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-(2-ethoxyethyl)ester-5-ethylester.

28. A pharmaceutical preparation according to claim 7 wherein said active ingredient is the compound 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-methylester-5-(2-methoxy-1,1-dimethylethyl)ester.

29. A pharmaceutical preparation according to claim 7 wherein said active ingredient is the compound 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-(2-methoxy)ethylester-5-propargyl ester.

30. A pharmaceutical preparation according to claim 7 wherein said active ingredient is the compound 2,6-dimethyl-4-(2,3-dichlorophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-methylester-5-(2-methyl)allylester.
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