Claims
- 1. A 4,7-dihydropyrazolo[3,4-b]-pyridine derivative represented by the formula: ##STR134## wherein R.sup.1 is (a) straight or branched chain C.sub.5 -C.sub.8 alkyl, (b) C.sub.4 -C.sub.6 cycloalkyl which may be substituted by lower alkyl, (c) C.sub.3 -C.sub.7 cycloalkyl (C.sub.1 -C.sub.4)alkyl, (d) C.sub.1 -C.sub.4 alkoxy-(C.sub.1 -C.sub.4)alkyl, (e) C.sub.4 -C.sub.7 cycloalkyloxy(C.sub.1 -C.sub.4)alkyl, (f) phenoxy(C.sub.1 -C.sub.4)alkyl, (g) C.sub.1 -C.sub.4 alkylthio(C.sub.1 -C.sub.4)alkyl, (h) C.sub.4 -C.sub.7 cycloalkylthio(C.sub.1 -C.sub.4)alkyl, (i) phenylthio(C.sub.1 -C.sub.4)alkyl, (j) C.sub.1 -C.sub.4 monalkylamino or C.sub.2 -C.sub.8 dialkylamino-substituted (C.sub.1 -C.sub.4)alkyl, (k) tetrahydrofuryl(C.sub.1 -C.sub.4)alkyl, (l) phenyl(C.sub.1 -C.sub.3)alkyl, which may have one or more substituents of halogen or C.sub.1 -C.sub.4 alkoxy, (m) N-benzylpyrrolidinyl, or (n) N-benzylpiperidinyl; R.sup.2 is C.sub.1 -C.sub.4 alkyl; and R.sup.3 is C.sub.4 -C.sub.6 cycloalkyl or C.sub.3 -C.sub.7 cycloalkyl(C.sub.1 -C.sub.4)alkyl; and the pharmaceutically acceptable acid addition salts thereof.
- 2. A compound as claimed in claim 1 in which R' is a halogenphenyl (C.sub.1 -C.sub.3) alkyl.
- 3. A compound claimed in claim 1, namely, cyclopentyloxyethyl 3-cyclopentyl-1,6-dimethyl-4-(2-nitrophenyl)-4,7-dihydropyrazolo-[3,4-b]pyridine-5-carboxylate.
- 4. A compound claimed in claim 1, namely, methylthioethyl 3-cyclopentyl-1,6-dimethyl-4-(2-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate.
- 5. A compound claimed in claim 1, namely, phenethyl 3-cyclopentyl-1,6-dimethyl-4-(2-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]-pyridine-5-carboxylate.
- 6. A compound claimed in claim 1, namely, cyclopentylethyl 3-cyclopentyl-1,6-dimethyl-4-(2-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate.
- 7. A compound claimed in claim 1, namely, (3-thienyl)ethyl 3-cyclopentyl-1,6-dimethyl-4-(2-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate.
- 8. A 4,7-dihydropyrazolo[3,4-b]pyridine derivative represented by the formula: ##STR135## wherein X and X.sup.1 each is hydrogen, nitro, or halogen which may be located at the position or positions 2, 3, and/or 6;
- R.sup.1 is C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.4 -C.sub.6 cycloalkyl, or phenyl;
- R.sup.3 is hydrogen, C.sub.1 -C.sub.8 straight or branched chain alkyl, C.sub.3 -C.sub.7 cycloalkyl which may be substituted by C.sub.1 -C.sub.3 alkyl, phenyl which may be substituted by chlorine, trifluoromethyl, cyano, methoxy, methoxycarbonyl or ethoxycarbonyl, C.sub.7 -C.sub.9 aralkyl or C.sub.1 -C.sub.4 alkoxycarbonyl; or pharmaceutically acceptable acid addition salts thereof.
- 9. A compound claimed in claim 8 wherein X is nitro, X' is hydrogen, R.sup.1 is C.sub.1 -C.sub.4 alkyl, R.sup.2 is C.sub.1 -C.sub.4 alkyl, R.sup.3 is C.sub.1 -C.sub.8 straight or branched chain alkyl, or C.sub.3 -C.sub.7 cycloalkyl.
- 10. A compound claimed in claim 9 wherein X is located at the 2 or 3 position of the phenyl.
- 11. A compound claimed in claim 9 wherein R.sup.3 is cyclopentyl or cyclohexyl.
- 12. A compound claimed in claim 8, namely, methyl 3-(n-butyl)-1,6-dimethyl-4-(3-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate.
- 13. A compound claimed in claim 8, namely, methyl 3-cyclobutyl-1,6-dimethyl-4-(3-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate.
- 14. A compound claimed in claim 8, namely, methyl 3-cyclopentyl-1,6-dimethyl-4-(3-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate.
- 15. A compound claimed in claim 8, namely, ethyl 3-cyclopentyl-1,6-dimethyl-4-(3-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate.
- 16. A compound claimed in claim 8, namely, methyl 3-cyclohexyl-1,6-dimethyl-4-(2-nitrophenyl)-4,7-dihydropyrazolo[3,4-b]pyridine-5-carboxylate.
- 17. An agent for treating cardiovascular diseases, comprising an effective amount for treating cardiovascular diseases of at least one substance selected from 4,7-dihydropyrazolo[3,4-b]pyridine derivatives represented by the formula: ##STR136## wherein R.sup.1 is (a) straight or branched chain C.sub.5 -C.sub.8 alkyl, (b) C.sub.4 -C.sub.6 cycloalkyl which may be substituted by lower alkyl, (c) C.sub.3 -C.sub.7 cycloalkyl (C.sub.1 -C.sub.4 )alkyl, (d) C.sub.1 -C.sub.4 alkoxy-(C.sub.1 -C.sub.4)alkyl, (e) C.sub.4 -C.sub.7 cycloalkyloxy(C.sub.1 -C.sub.4)alkyl, (f) phenoxy(C.sub.1 -C.sub.4)alkyl, (g) C.sub.1 -C.sub.4 alkylthio(C.sub.1 -C.sub.4)alkyl, (h) C.sub.4 -C.sub.7 cycloalkylthio(C.sub.1 -C.sub.4)alkyl, (i) phenylthio(C.sub.1 -C.sub.4)-alkyl, (j) C.sub.1 -C.sub.4 monalkylamino or C.sub.2 -C.sub.8 dialkylamino-substituted (C.sub.1 -C.sub.4)alkyl, (k) tetrahydrofuryl(C.sub.1 -C.sub.4)alkyl, (l) phenyl(C.sub.1 -C.sub.3)alkyl, which may have one or more substituents of halogen or C.sub.1 -C.sub.4 alkoxy, [or trifluoroalkyl,] (m) N-benzylpyrrolidinyl, or (n) N-benzylpiperidinyl; R.sup.2 is C.sub.1 -C.sub.4 alkyl; and R.sup.3 is C.sub.4 -C.sub.6 cycloalkyl or C.sub.3 -C.sub.7 cycloalkyl(C.sub.1 -C.sub.4)alkyl or the pharmaceutically acceptable acid addition salts thereof and a pharmaceutically acceptable carrier.
- 18. An agent for treating cardiovascular diseases, comprising an effective amount for treating cardiovascular diseases of at least one substance selected from 4,7-dihydropyrazolo[3,4-b]pyridine derivatives represented by the formula: ##STR137## wherein X and X.sup.1 each is hydrogen, nitro, or halogen which may be located at the position or positions 2, 3, and/or 6; R.sup.1 is C.sub.1 -C.sub.4 alkyl; R.sup.2 is hydrogen, C.sub.1 -C.sub.4 alkyl, C.sub.4 -C.sub.6 cycloalkyl, or phenyl; R.sup.3 is hydrogen, C.sub.1 -C.sub.8 straight or branched chain alkyl, C.sub.3 -C.sub.7 cycloalkyl which may be substituted by C.sub.1 -C.sub.3 alkyl, phenyl which may be substituted by chlorine, trifluoromethyl, cyano, methoxy, methoxycarbonyl or ethoxycarbonyl, C.sub.7 -C.sub.9 aralkyl or C.sub.1 -C.sub.4 alkoxycarbonyl; or pharmaceutically acceptable acid addition salts thereof and a pharmaceutically acceptable carrier.
Priority Claims (2)
Number |
Date |
Country |
Kind |
57-176763 |
Oct 1982 |
JPX |
|
69-53118 |
Mar 1984 |
JPX |
|
Parent Case Info
This is a CIP application of U.S. application Ser. No. 709,795 filed Mar. 8, 1985 now abandoned, and U.S. application Ser. No. 018,815, filed Feb. 19, 1987 now abandoned, the latter application being a continuation of U.S. application Ser. No. 527,733, filed Aug. 30, 1983 now abandoned.
US Referenced Citations (1)
Number |
Name |
Date |
Kind |
4562256 |
Adachi et al. |
Dec 1985 |
|
Foreign Referenced Citations (2)
Number |
Date |
Country |
0107619 |
May 1984 |
EPX |
0114273 |
Aug 1984 |
EPX |
Continuations (1)
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Number |
Date |
Country |
Parent |
527733 |
Aug 1983 |
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Continuation in Parts (2)
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Number |
Date |
Country |
Parent |
709795 |
Mar 1985 |
|
Parent |
18815 |
Feb 1987 |
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