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Generated: November 21, 2017

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Claims for Patent: 5,583,141

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Claims for Patent: 5,583,141

Title: Heterocyclic compounds and their use as angiotensin antagonists
Abstract:
Inventor(s): Naka; Takehiko (Hyogo, JP), Inada; Yoshiyuki (Hyogo, JP)
Assignee: Takeda Chemical Industries, Ltd. (Osaka, JP)
Application Number:08/291,435
Patent Claims: 1. A compound or a salt thereof: ##STR71## wherein R.sup.1 is an optionally substituted hydrocarbon residue which is optionally bound through a hetero-atom;

R.sup.2 is a group of the formula: ##STR72## wherein i is --O-- or --S-- and j is >c=0 or >c=S;

R.sup.3 is optionally esterified or amidated carboxyl, tetrazolyl, trifluoromethanesulfonic amide, phosphoric acid or sulfonic acid, which may be protected with optionally substituted lower alkyl or acyl and the group of the formula ##STR73## has a structure selected from the group consisting of ##STR74## wherein in addition to R.sup.1 and R.sup.3, a methyl substituent may be provided, and wherein h is CH.sub.2, C.dbd.O, C.dbd.S, S--(O).sub.m, NR.sup.9 and O wherein m denotes an integer of 0-2 and R.sup.9 is hydrogen or lower(1-4C)alkyl, and excluding the compound 2-ethoxy-1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]meth yl]benzimidazole-7-carboxylic acid and its physiologically acceptable salts.

2. A compound or a salt thereof according to claim 1, wherein R.sup.1 is lower (C.sub.2-4) alkyl which may be bound through --O--, --NH-- or --S--.

3. A compound or a salt thereof according to claim 1, wherein R.sup.3 is a group of the formula: --CO--D wherein D is hydroxy, amino, N-lower (C.sub.1-4) alkylamino, N, N-di-lower (C.sub.1-4) alkylamino, lower (C.sub.1-6) alkoxy, lower (C.sub.1-6) alkylthio or optionally substituted dioxolenyl, or a group of the formula: --O--CH(R.sup.4)--OCOR.sup.5 wherein R.sup.4 is hydrogen, lower (C.sub.1-6) alkyl, lower (C.sub.2-6) alkenyl or lower (C.sub.3-8) cycloalkyl; and R.sup.5 is lower (C.sub.1-6) alkyl, lower (C.sub.2-6) alkenyl, lower (C.sub.3-8) cycloalkyl, lower (C.sub.1-3) alkyl substituted with lower (C.sub.3-8) cycloalkyl or aryl, lower (C.sub.2-3) alkenyl optionally substituted with lower (C.sub.3-8) cycloalkyl or aryl, aryl, lower (C.sub.1-6) alkoxy, lower (C.sub.2-8) alkenyloxy, lower (C.sub.3-8) cycloalkyloxy, lower (C.sub.1-3) alkoxy substituted with lower (C.sub.3-8) cycloalkyl or aryl, lower (C.sub.2-3) alkenyloxy substituted with lower (C.sub.3-8) cycloalkyl or aryl, or aryloxy.

4. A compound or a salt thereof according to claim 1, wherein R.sup.3 is a group of the formula: --CO--D" wherein D" is hydroxy, amino, N-lower (C.sub.1-4) alkylamino, N,N-di-lower (C.sub.1-4) alkylamino or lower (C.sub.1-4) alkoxy whose alkyl moiety may be substituted by hydroxy, amino, halogen, lower (C.sub.2-6) alkanoyloxy, 1-lower (C.sub.1-6) alkoxycarbonyl or lower (C.sub.1-4) alkoxy, or tetrazolyl optionally protected with lower (C.sub.1-4) alkyl or acyl.

5. A compound or a salt thereof according to claim 1, wherein R.sup.3 is optionally esterified carboxyl.

6. A compound or a salt thereof according to claim 1, wherein the group of the formula: ##STR75## is benzimidazole, thienoimidazole or imidazopyridine structure.

7. A compound or a salt thereof according to claim 1, wherein the group ##STR76##

8. A compound or a salt thereof according to claim 1, wherein R.sup.3 is optionally esterified or amidated carboxyl.

9. A compound or a salt thereof according to claim 8, wherein R.sup.3 is a group of the formula: --CO--D wherein D is hydroxy, optionally substituted amino or optionally substituted alkoxy.

10. A compound or a salt thereof according to claim 9, wherein the optionally substituted alkoxy is lower (C.sub.1-6) alkoxy whose alkyl moiety may be substituted by hydroxy, optionally substituted amino, halogen, lower (C.sub.1-6) alkoxy, lower (C.sub.1-6) alkylthio or optionally substituted dioxolenyl, or a group of the formula: --O--CH(R.sup.4)--OCOR.sup.5 wherein R.sup.4 is hydrogen, lower (C.sub.1-6) alkyl, lower (C.sub.2-6) alkenyl or lower (C.sub.3-8) cycloalkyl; and R.sup.5 is lower (C.sub.1-6) alkyl, lower (C.sub.2-6) alkenyl, lower (C.sub.3-8) cycloalkyl, lower (C.sub.1-3) alkyl substituted with lower (C.sub.3-8) cycloalkyl or aryl, lower (C.sub.2-3) alkenyl optionally substituted with lower (C.sub.3-8) cycloalkyl or aryl, aryl, lower (C.sub.1-6) alkoxy, lower (C.sub.2-8) alkenyloxy, lower (C.sub.3-8) cycloalkyloxy, lower (C.sub.1-3) alkoxy substituted with lower (C.sub.3-8) cycloalkyl or aryl, lower (C.sub.2-3) alkenyloxy substituted with lower (C.sub.3-8) cycloalkyl or aryl, or aryloxy.

11. A compound or a salt thereof according to claim 8, wherein R.sup.3 is carboxyl.

12. A compound or a salt thereof according to claim 1, wherein R.sup.1 is alkyl, alkenyl, alkynyl or cycloalkyl which may be bound through a group of the formula: --N(R.sup.9)-- wherein R.sup.9 is hydrogen or lower (C.sub.1-4) alkyl, --O-- or --S(O).sub.m -- wherein m is an integer of 0 to 2 and which may be substituted with hydroxy, optionally substituted amino, halogen, lower (C.sub.1-4) alkoxy or lower (C.sub.1-4) alkylthio.

13. A compound or a salt thereof according to claim 1, wherein R.sup.1 is aryl or aralkyl which may be bound through a group of the formula: --N(R.sup.9)-- wherein R.sup.9 is hydrogen or lower (C.sub.1-4) alkyl, --O-- or --S(O).sub.m -- wherein m is an integer of 0 to 2 and which may be substituted with halogen, nitro, optionally substituted amino, lower (C.sub.1-4) alkoxy, lower (C.sub.1-4) alkylthio or lower (C.sub.1-4) alkyl.

14. A compound or a salt thereof according to claim 1, wherein R.sup.1 is lower (C.sub.1-8) alkyl or lower (C.sub.2-8) alkenyl which may be bound through a group of the formula: --N(R.sup.9)-- wherein R.sup.9 is hydrogen or lower (C.sub.1-4) alkyl, --O-- or --S(O).sub.m wherein m is an integer of 0 to 2 and which may be substituted with hydroxy, amino, N-lower (C.sub.1-4) alkylamino, N,N-dilower (C.sub.1-4) alkylamino, halogen, lower (C.sub.1-4) alkoxy or lower (C.sub.1-4) alkylthio.

15. A compound or a salt thereof according to claim 1, wherein R.sup.1 is lower (C.sub.1-5) alkyl or lower (C.sub.2-5) alkenyl which may be bound through a group of the formula: --N(R.sup.9)-- wherein R.sup.9 is hydrogen or lower (C.sub.1-4) alkyl, --O-- or --S(O).sub.m -- wherein m is an integer of 0 to 2 and which may be substituted with hydroxy, amino, halogen or lower (C.sub.1-4) alkoxy.

16. A compound or a salt thereof according to claim 1, wherein R.sup.2 is 2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl group.

17. A compound or a salt thereof according to claim 1, wherein R.sup.2 is 2,5-dihydro-5-oxo-1,2,4-thiadiazol-3-yl group.

18. A compound or a salt thereof according to claim 1, wherein R.sup.2 is 2,5-dihydro-5-thioxo-1,2,4-oxadiazol-3-yl group.

19. A compound or a salt according to claim 1, wherein the group of the formula: ##STR77## is benzimidazole or imidazopyridine.

20. A compound or a salt according to claim 19, wherein R.sup.2 is 2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl or 2,5-dihydro-5-oxo-1,2,4-thiadiazol-3-yl.

21. A compound or a salt according to claim 1, wherein the group of the formula: ##STR78## has a structure selected from the group consisting of ##STR79##

22. A compound or a salt according to claim 21, wherein R.sup.2 is 2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl or 2,5-dihydro-5-oxo-1,2,4-thiadiazol-3-yl.

23. A compound or a salt thereof of formula: ##STR80## wherein R.sup.1 is lower (C.sub.1-5) alkyl which may be bound through --O--, --NH-- or --S-- and which may be substituted with hydroxy, amino, N-lower (C.sub.1-4) alkylamino, N,N-di-lower (C.sub.1-4) alkylamino, halogen, lower (C.sub.1-4) alkoxy or lower (C.sub.1-4) alkylthio;

R.sup.2 is a group of the formula: ##STR81## wherein i is --O-- or --S--and j is >c=0 or >c=S;

R.sup.3 is optionally esterified or amidated carboxyl, tetrazolyl, trifluoromethanesulfonic amide, phosphoric acid or sulfonic acid, which may be protected with optionally substituted lower alkyl or acyl and the group of the formula ##STR82## has a structure selected from the group consisting of ##STR83## wherein in addition to R.sup.1 and R.sup.3, a methyl substituent may be provided, and excluding the compound 2-ethoxy-1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]meth yl]benzimidazole-7-carboxylic acid and its physiologically acceptable salts thereof.

24. A compound according to claim 1, which is 1-(cyclohexyloxycarbonyloxy)ethyl 2-ethoxy-1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]meth yl]benzimidazole-7-carboxylate.

25. A compound according to claim 1, which is 1-[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl-4-methy l-2-propoxythieno[3,4-d]imidazole-6-carboxylic acid.

26. A compound according to claim 1, which is 2-ethyl-1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methy l]benzimidazole-7-carboxylic acid.

27. A compound according to claim 1, which is 2-ethoxy-1-[[2'-(2,5-dihydro-5-oxo-1,2,4-thiadiazol-3-yl)biphenyl-4-yl]met hyl]benzimidazole-7-carboxylic acid.

28. A compound according to claim 1, which is 2-ethyl-3-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methy l]-5,7-dimethylimidazo[4.5-b]pyridine.

29. A compound according to claim 1, which is 1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]2-meth oxy-4-methylthieno[3,4-d]imidazole-6-carboxylic acid.

30. A compound according to claim 1, which is 2-cyclopropyl-1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl ]methyl]benzimidazole-7-carboxylic acid.

31. A pharmaceutical composition for antagonizing angiotensin II which comprises a therapeutically effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof in admixture with a pharmaceutical acceptable carrier, excipient or diluent.

32. A method for antagonizing angiotensin II in a mammal which comprises administering to said mammal a therapeutically effective amount of a compound according to claim 1 or a pharmaceutically acceptable salt thereof.
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