Claims
- 1. 1,4-Dihydropyridine derivatives of formula (I): ##STR162## wherein Ar.sup.1 represents a naphthyl group which may have a substituent, or an aromatic heterocyclic group selected from the group consisting of pyridyl group, quinolyl group, isoquinolyl group, furyl group, thienyl group, benzoxazolyl group, benzothiazolyl group, pyridazinyl group, pyrazinyl group, pyrimidinyl group, indolyl group, benzoxadiazolyl group and benzothiadiazolyl group, which aromatic heterocyclic group may have a substituent, and Ar.sup.2 represents an aromatic hydrocarbon group which may have a substituent, or an aromatic heterocyclic group which may have a substituent; R.sup.1 represents a group selected from the group consisting of --CO.sub.2 R.sup.2, --SO.sub.2 R.sup.3, --COR.sup.4, --CON(R.sup.5).sub.2, --CN or --NO.sub.2 ; R.sup.2 represents (i) hydrogen, (ii) a straight chain, branched chain or cyclic saturated hydrocarbon group having 1 to 10 carbon atoms, which may have a substituent selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, a phenoxy group which may have a substituent, a phenylthio group which may have a substituent, a substituted amino group, a cyclic amino group which may have a substituent, a phenyl group which may have a substituent, an aromatic heterocyclic group which may have a substituent, and a trihalomethyl group, or (iii) a straight chain, branched chain or cyclic unsaturated hydrocarbon group having 2 to 10 carbon atoms, which may have a substituent selected from the group consisting of an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a phenoxy group which may have a substituent, a phenylthio group which may have a substituent, a substituted amino group, a cyclic amino group which may have a substituent, a phenyl group which may have a substituent, an aromatic heterocyclic group which may have a substituent, and a trihalomethyl group; R.sup.3 represents an alkyl group having 1 to 4 carbon atoms; R.sup.4 represents an alkyl group having 1 to 4 carbon atoms, or a phenyl group; and R.sup.5 represents an alkyl group having 1 to 4 carbon atoms.
- 2. The 1,4-dihydropyridine derivatives as claimed in claim 1, wherein the substituent of the aromatic heterocyclic group represented by Ar.sup.1 is selected from the group consisting of a halogen, cyano group, nitro group, trifluoromethyl group, trichloromethyl group, azide group, amide group, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, benzoyl group, an alkylthio group having 1 to 4 carbon atoms, phenylthio group, phenoxy group, a lower alkoxycarbonyl group, a lower acyl group, benzyloxy group, hydroxy group, and cinnamyloxy group.
- 3. The 1,4-dihydropyridine derivatives as claimed in claim 1, wherein Ar.sup.2 represents an aromatic hydrocarbon group selected from the group consisting of phenyl group and naphthyl group, each of which may have a substituent.
- 4. The 1,4-dihydropyridine derivatives as claimed in claim 1, wherein Ar.sup.2 represents an aromatic heterocyclic group selected from the group consisting of pyridyl group, quinolyl group, isoquinolyl group, furyl group, thienyl group, benzoxazolyl group, benzothiazolyl group, pyridazinyl group, pyrazinyl group, pyrimidinyl group, indolyl group, benzoxadiazolyl group, and benzothiadiazolyl group, each of which may have a substituent.
- 5. The 1,4-dihydropyridine derivatives as claimed in claim 3, wherein the substituent of the aromatic hydrocarbon group represented by either Ar.sup.2 is selected from the group consisting of a halogen, cyano group, nitro group, trifluoromethyl group, trichloromethyl group, azide group, amide group, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, a benzoyl group, an alkylthio group having 1 to 4 carbon atoms, phenylthio group, phenoxy group, a lower alkoxycarbonyl group, a lower acyl group, benzyloxy group, hydroxy group, and cinnamyloxy group.
- 6. The 1,4-dihydropyridine derivatives as claimed in claim 4, wherein the substituent of the aromatic heterocyclic group represented by Ar.sup.2 is selected from the group consisting of a halogen, cyano group, nitro group, trifluoromethyl group, trichloromethyl group, azide group, amide group, an alkyl group having 1 to 4 carbon atoms, an alkoxyl group having 1 to 4 carbon atoms, benzoyl group, an alkylthio group having 1 to 4 carbon atoms, phenylthio group, phenoxy group, a lower alkoxycarbonyl group, a lower acyl group, benzyloxy group, hydroxy group, and cinnamyloxy group.
- 7. The 1,4-dihydropyridine derivatives as claimed in claim 1, wherein Ar.sup.2 is selected from the group consisting of phenyl group, 2-nitrophenyl group, 3-nitrophenyl group, 4-nitrophenyl group, 2-cyanophenyl group, 2-bromophenyl group, 3-bromophenyl group, 4-bromophenyl group, 2-chlorophenyl group, 3-chlorophenyl group, 4-chlorophenyl group, 2-iodophenyl group, 3-iodophenyl group, 4-iodophenyl group, 3-cyanophenyl group, 4-cyanophenyl group, 2,3-dichlorophenyl group, 2,6-dichlorophenyl group, 3,5-dichlorophenyl group, 2-furyl group, furyl group, thienyl group, 3-thienyl group, 1-naphthyl group, naphthyl group, 3-azidophenyl group, 2-trifluoromethylphenyl group, 3-trifluoromethylphenyl group, 4-trifluoromethylphenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 2-hydroxyphenyl group, 3-hydroxyphenyl group, 4-hydroxyphenyl group, 2-benzyloxyphenyl group, 3-benzyloxyphenyl group, 2-cinnamyloxyphenyl group, 3-cinnamyloxyphenyl group, 3-benzoylphenyl group, 2-methoxyphenyl group, 3-methoxyphenyl group, 4-methoxyphenyl group, 4-methylthiophenyl group, 3-trichloromethylphenyl group, 2-pyridyl group, pyridyl group, 4-pyridyl group, quinolyl group, 3-quinolyl group, 4-quinolyl group, 1-isoquinolyl group, quinoxalyl group, 2-chloropyridyl group, 6-chloropyridyl group, 2-methylpyridyl group, 6-methylpyridyl group, 2-methoxypyridyl group, 6-methoxypyridyl group, 5-bromopyridyl group, 2-amionpyridyl group, 2-mercaptopyridyl group, pyridazinyl group, 4-pyridazinyl group, pyrazinyl group, pyrimidinyl group, 5-pyrimidinyl group, 7-benzoxazolyl group, 7-benzothiazolyl group, 3-benzoxadiazolyl group, 3-benzothiazolyl group, 2-indolyl group, 3-indolyl group, and 5-indolyl group.
- 8. The 1,4-dihydropyridine derivatives as claimed in claim 1, wherein R.sup.1 is --CO.sub.2 R.sup.2, in which R.sup.2 is hydrogen.
- 9. The 1,4-dihydropyridine derivatives as claimed in claim 1, wherein R.sup.1 is --CO R.sup.2, in which R.sup.2 is a straight chain or branched saturated hydrocarbon group selected from the group consisting of methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, isoproyl group, and isobutyl group, each of which may have a substituent.
- 10. The 1,4-dihydropyridine derivatives as claimed in claim 1, wherein R.sup.1 is --CO.sub.2 R.sup.2, in which R.sup.2 is a cyclic hydrocarbon group selected from the group consisting of cyclopentyl group and cyclohexyl group, each of which may have a substituent.
- 11. The 1,4-dihydropyridine derivatives as claimed in claim 1, wherein R.sup.1 is --CO.sub.2 R.sup.2, in which R.sup.2 is an unsaturated hydrocarbon group selected from the group consisting of propenyl group, 2-butenyl group, 3-butenyl group, 2-pentenyl group, 2,4-hexadienyl group, 2,4-hexadiynyl group, hexa-4-en-2-yne, each of which may have a substituent.
- 12. The 1,4-dihydropyridine derivatives as claimed in claim 9, wherein the substituent of R.sup.2 is selected from the group consisting of an alkoxyl group having 1 to 6 carbon atoms, an unsubstituted or substituted phenoxy group, an unsubstituted or substituted phenylthio group, a substituted amino group, cyclic amino group, an unsubstituted or substituted phenyl group, an unsubstituted or substituted pyridyl group, an aromatic heterocyclic group, and a trihalomethyl group.
- 13. The 1,4-dihydropyridine derivatives as claimed in claim 10, wherein the substituent of R.sup.2 is selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, an unsubstituted or substituted phenoxy group, an unsubstituted or substituted phenylthio group, a substituted amino group, a cyclic amino group, an unsubstituted or substituted phenyl group, an unsubstituted or substituted pyridyl group, an aromatic heterocyclic group, and a trihalomethyl group.
- 14. The 1,4-dihydropyridine derivatives as claimed in claim 11, wherein the substituent of R.sup.2 is selected from the group consisting of an alkyl group having 1 to 6 carbon atoms, an alkyl group having 1 to 6 carbon atoms, an unsubstituted or substituted phenoxy group, an unsubstituted or substituted phenylthio group, a substituted amino group, cyclic amino group, an unsubstituted or substituted phenyl group, an unsubstituted or substituted pyridyl group, an aromatic heterocyclic group, and a trihalomethyl group.
- 15. The 1,4-dihydropyridine derivatives as claimed in claim 12, wherein said alkoxyl group is selected from the group consisting of methoxy group, ethoxy group and propoxy group.
- 16. The 1,4-dihydropyridine derivatives as claimed in claim 12, wherein said substituted amino group is selected from the group consisting of dimethyl amino group, diethyl amino group, and N-benzyl-N-methylamino group.
- 17. The 1,4-dihydropyridine derivatives as claimed in claim 12, wherein said cyclic amino group is selected from the group consisting of an unsubstituted or substituted piperazinyl group and piperidinyl group.
- 18. The 1,4-dihydropyridine derivatives as claimed in claim 12, wherein said aromatic heterocyclic group is selected from the group consisting of pyridyl group, quinolyl group, isoquinolyl group, furyl group, thienyl group, benzoxazolyl group, benzothiazolyl group, pyridazinyl group, pyrazinyl group, pyrimidinyl group, indolyl group, benzoxadiazolyl group, and benzothiadiazolyl group.
- 19. The 1,4-dihydropyridine derivatives as claimed in claim 13, wherein said alkyl group is selected from the group consisting of methyl group, ethyl group, propyl group, and isopropyl group.
- 20. The 1,4-dihydropyridine derivatives as claimed in claim 13, wherein said alkoxyl group is selected from the group consisting of methoxy group, ethoxy group and propoxy group.
- 21. The 1,4-dihydropyridine derivatives as claimed in claim 13, wherein said substituted amino group is selected from the group consisting of dimethyl amino group, diethyl amino group, and N-benzyl-N-methylamino group.
- 22. The 1,4-dihydropyridine derivatives as claimed in claim 13, wherein said cyclic amino group is selected from the group consisting of an unsubstituted or substituted piperazinyl group and piperidinyl group.
- 23. The 1,4-dihydropyridine derivatives as claimed in claim 13, wherein said aromatic heterocyclic group is selected from the group consisting of pyridyl group, quinolyl group, isoquinolyl group, furyl group, thienyl group, benzoxazolyl group, benzothiazolyl group, pyridazinyl group, pyrazinyl group, pyrimidinyl group, indolyl group, benzoxadiazolyl group, and benzothiadiazolyl group.
- 24. The 1,4-dihydropyridine derivatives as claimed in claim 14, wherein said alkyl group is selected from the group consisting of methyl group, ethyl group, propyl group, and isopropyl group.
- 25. The 1,4-dihydropyridine derivatives as claimed in claim 14, wherein said alkoxyl group is selected from the group consisting of methoxy group, ethoxy group and propoxy group.
- 26. The 1,4-dihydropyridine derivatives as claimed in claim 14, wherein said substituted amino group is selected from the group consisting of dimethyl amino group, diethyl amino group, and N-benzyl-N-methylamino group.
- 27. The 1,4-dihydropyridine derivatives as claimed in claim 14, wherein said cyclic amino group is selected from the group consisting of an unsubstituted or substituted piperazinyl group and piperidinyl group.
- 28. The 1,4-dihydropyridine derivatives as claimed in claim 14, wherein said aromatic heterocyclic group is selected from the group consisting of pyridyl group, quinolyl group, isoquinolyl group, furyl group, thienyl group, benzoxazolyl group, benzothiazolyl group, pyridazinyl group, pyrazinyl group, pyrimidinyl group, indolyl group, benzoxadiazolyl group, and benzothiadiazolyl group.
- 29. The 1,4-dihydropyridine derivatives as claimed in claim 1, wherein R.sup.1 is --CO.sub.2 R.sup.2, in which R.sup.2 is selected from the group consisting of hydrogen, methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-octyl group, n-nonyl group, n-decyl group, isopropyl group, isobutyl group, cyclopentyl group, cyclohexyl group, 2-propene-1-yl group, 2-propyne-1-yl group, [E)-2-butene-1-yl group, (E)-3-butene-1-yl group, (E)-2-pentene-1-yl group, (2E,4E)-2,4-hexadienyl group, 2,4-hexadiynyl group, (E)-hexa-4-en-2-yne group, (E)-3-phenyl-2-propene-1-yl group, (Z)-3-phenyl-2-propyne-1-yl group, 3-phenyl-2-propyne-1-yl group, [2E,4E)-5-phenyl-2,4-pentadiene-1-yl group, 5-phenyl-penta-2,4-diyne-1-yl group, (E)-5-phenyl-penta-2-en-4-yne-1-yl group, (E)-3-[4-(1-imidazolylmethyl)phenyl]-2-propene-1-yl group, (E)-3-[3-(1-imidazolylmethyl}phenyl]-2-propene-1-yl group, (E)-3-[2-[1-imidazolylmethyl)phenyl]-2-propene-1-yl group, (Z)-3-[4-(1-imidazolylmethyl)phenyl]-2-propene-1-yl group, (E)-3-[6-(1-imidazolylmethyl)pyridine-2-yl]-2-propene-1-yl group, (E)-3-[5-(1-imidazolylmethyl)furan-2-yl]-2-propene-1-yl group, (E)-3-[5-(1-imidazolylmethyl)thiophene-2-yl]-2-propene-1-yl group, (E)-3-phenyl-1-methyl-2-propene-1-yl group, (E)-2-fluoro-3-phenyl-2-propene-1-yl group, 2-methoxyethyl group, 3-methoxypropyl group, 3-ethoxypropyl group, 2-phenoxyethyl group, 2-phenylthioethyl group, 2-(N-methylamino)ethyl group, 2-(N,N-dimethylamino)-ethyl group, 2-(N-methyl-N-phenylamino)ethyl group, 2-N,N-diethylamino)ethyl group, 2-(N-benzyl-N-methylamino)-ethyl group, 2-(1-piperazinyl)ethyl group, 4-(1-piperazinyl)butyl group, 6-(1-piperazinyl)hexyl group, 2-(1-piperidinyl)ethyl group, 2-(4-phenylpiperazine-1-yl)-ethyl group, 3-(4-phenylpiperazine-1-yl)propyl group, 4-4-phenylpiperazine-1-yl)butyl group, 6-(4-phenylpiperadine-1-yl)hexyl group, 2-(4-phenylpiperidine-1-yl)-ethyl group, 3-(4-phenylpiperidine-1-yl)propyl group, 4-(4-phenylpiperidine-1-yl)butyl group, 4-(4-phenylpiperidine-1-yl)butyl group, 6-(4-phenylpiperidine-1-yl)hexyl group, 2-[4-(diphenylmethyl)piperazine-1-yl]ethyl group, 3-[4-(diphenylmethyl)piperazine-1-yl)propyl group, 4-[4-(diphenylmethyl)piperazine-1-yl)]butyl group, 6-[4-[diphenylmethyl)piperazine-1-yl)]hexyl group, 2-morpholinoethyl group, N-benzylpyrrolidine-3-yl group, N-benzylpiperidine-3-yl group, 2-[1,2,3,4-tetrahydroisoquinoline-2-yl)ethyl group, 2,2,2-trifluoroethyl group, 2-(3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione-1-yl)ethyl group, and 2-(1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-7H-purine-7-yl)ethyl group.
- 30. The 1,4-dihydropyridine derivatives as claimed in claim 1, wherein R.sup.1 is --SO.sub.2 R.sup.3, in which R.sup.3 is an alkyl group having 1 to 4 carbon atoms.
- 31. The 1,4-dihydropyridine derivatives as claimed in claim 30, wherein the alkyl group represented by R.sup.3 is selected from the group consisting of methyl group, ethyl group, n-propyl group, and isopropyl group.
- 32. The 1,4-dihydropyridine derivatives as claimed in claim 1, wherein R.sup.1 is --COR.sup.4, in which R.sup.4 is an alkyl group having 1 to 4 carbon atoms.
- 33. The 1,4-dihydropyridine derivatives as claimed in claim 32, wherein the alkyl group represented by R.sup.4 is selected from the group consisting of methyl group, ethyl group, n-propyl group, and isopropyl group.
- 34. The 1,4-dihydropyridine derivatives as claimed in claim 1, wherein R.sup.1 is --COR.sup.4, in which R.sup.4 is a phenyl group.
- 35. The 1,4-dihydropyridine derivatives as claimed in claim 1, wherein R.sup.1 is --CON(R.sup.5).sub.2, in which R.sup.5 is an alkyl group having 1 to 4 carbon atoms.
- 36. The 1,4-dihydropyridine derivatives as claimed in claim 35, wherein the alkyl group represented by R.sup.5 is selected from the group consisting of methyl group, ethyl group, n-propyl group, and isopropyl group.
Priority Claims (1)
Number |
Date |
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Kind |
1-136208 |
May 1989 |
JPX |
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Parent Case Info
This application is a continuation of application Ser. No. 07/529,445, filed on May 29, 1990, now abandoned.
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Entry |
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Continuations (1)
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Number |
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Parent |
529445 |
May 1990 |
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