Patent US4892875A successfully refreshed from Google Patents.
US4892875A
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Substituted heterocyclylalkyl esters of 1,4-dihydropyridine-3,5-dicarboxylic acids
Assignee: Takeda Pharmaceutical Co Ltd
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Filing: 1985-01-22
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Granted: 1990-01-09
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Expires: 2005-01-22
Abstract
Abstract Dihydropyridine derivatives and acid addition salts thereof which are of use as prophylactic or/and therapeutic drugs for cardiovascular diseases, said dihydropyridine derivatives having the formula <IMAGE> wherein R1, R2 and R3 are the same or different and each is alkyl, cycloalkyl, cycloalkylalkyl or alkoxyalkyl; R4 and R5 are the same or different and each is hydrogen, halogen, nitro, trifluoromethyl, alkyl, cycloalkyl, alkoxy, cyano, alkoxycarbonyl or alkylthio; R6 is hydrogen, alkyl, cycloalkyl, aralkyl, aryl or a pyridyl; X is oxygen, sulfur, vinylene, azomethine or a group of the formula <IMAGE> A is alkylene; Ar is aryl or a pyridyl; m is an integer of 1 to 3; n is an integer of 0 to 2.
Inventors
- 👤 Kanji Meguro
- 👤 Akinobu Nagaoka
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 17:17
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/80; C07D211/84; C07D211/90; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/72; C07D213/74; C07D243/00; C07D243/06; C07D243/08; C07D295/00; C07D295/04; C07D295/08; C07D295/084; C07D295/088; C07D401/00; C07D401/02; C07D401/12; C07D405/00; C07D405/02; C07D405/04; C07D409/00; C07D409/02; C07D409/04; C07D413/00; C07D413/02; C07D413/04; C07D417/00; C07D417/02; C07D417/04
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
239 words
A dihydropyridine compound of the formula ##STR60## wherein R 1 , R 2 and R 3 are the same or different and each is C 1-6 -alkyl, C 3-6 -cycloalkyl, C 3-6 -cycloalkyl-C 1-6 -alkyl, or C 3-7 -alkoxyalkyl; R 4 and R 5 are the same or different and each is hydrogen, halogen, nitro, trifluoromethyl, C 1-6 -alkyl, C 3-6 -cycloalkyl, C 1-3 -alkoxy, cyano, C 2-4 -alkoxycarbonyl or C 1-3 -alkylthio; R 6 is hydrogen, C 1-6 -alkyl, C 3-6 -cycloalkyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, phenyl-C 1-3 -alkyl optionally substituted on the phenyl ring by halogen, nitro trifluoromethyl, C 1-6 -alkyl, C 3-6 -cycloalkyl, C 1-3 -alkoxy, cyano, C 1-3 -alkylthio and C 2-4 -alkoxycarbonyl groups, or phenyl, or naphthyl, wherein the phenyl or naphthyl groups can be optionally substituted by one or two halogen, nitro, trifluormethyl, C 1-6 -alkyl, C 3-6 -cycloalkyl, C 1-3 -alkoxy, cyano, C 1-3 -alkylthio and C 2-4 -alkoxycarbonyl groups; A is C 2-4 -alkylene; Ar is 2-pyridyl, 3-pyridyl, 4-pyridyl or phenyl or naphthyl which phenyl or naphthyl can be optionally substituted by one or two nitro, trifluoromethyl, halogen, C 1-6 -alkyl, C 3-6 -cycloalkyl, C 1-3 -alkoxy, cyano, C 1-3 -alkylthio and C 2-4 -alkoxycarbonyl groups; m is an integer of 1 to 3 inclusive; n is an integer of 1 or 2, and wherein ##STR61## represents phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furyl, 2-thienyl, 2,1,3-benzoxadiazol-4-yl, or 2,1,3-benzothiadiazol-4-yl; or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
239 words
A dihydropyridine compound of the formula ##STR60## wherein R 1 , R 2 and R 3 are the same or different and each is C 1-6 -alkyl, C 3-6 -cycloalkyl, C 3-6 -cycloalkyl-C 1-6 -alkyl, or C 3-7 -alkoxyalkyl; R 4 and R 5 are the same or different and each is hydrogen, halogen, nitro, trifluoromethyl, C 1-6 -alkyl, C 3-6 -cycloalkyl, C 1-3 -alkoxy, cyano, C 2-4 -alkoxycarbonyl or C 1-3 -alkylthio; R 6 is hydrogen, C 1-6 -alkyl, C 3-6 -cycloalkyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, phenyl-C 1-3 -alkyl optionally substituted on the phenyl ring by halogen, nitro trifluoromethyl, C 1-6 -alkyl, C 3-6 -cycloalkyl, C 1-3 -alkoxy, cyano, C 1-3 -alkylthio and C 2-4 -alkoxycarbonyl groups, or phenyl, or naphthyl, wherein the phenyl or naphthyl groups can be optionally substituted by one or two halogen, nitro, trifluormethyl, C 1-6 -alkyl, C 3-6 -cycloalkyl, C 1-3 -alkoxy, cyano, C 1-3 -alkylthio and C 2-4 -alkoxycarbonyl groups; A is C 2-4 -alkylene; Ar is 2-pyridyl, 3-pyridyl, 4-pyridyl or phenyl or naphthyl which phenyl or naphthyl can be optionally substituted by one or two nitro, trifluoromethyl, halogen, C 1-6 -alkyl, C 3-6 -cycloalkyl, C 1-3 -alkoxy, cyano, C 1-3 -alkylthio and C 2-4 -alkoxycarbonyl groups; m is an integer of 1 to 3 inclusive; n is an integer of 1 or 2, and wherein ##STR61## represents phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furyl, 2-thienyl, 2,1,3-benzoxadiazol-4-yl, or 2,1,3-benzothiadiazol-4-yl; or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
227 words
A dihydropyridine compound of the formula ##STR62## wherein R 1 , R 2 and R 3 are the same or different and each is C 1-6 -alkyl, C 3-6 -cycloalkyl, C 3-6 -cycloalkyl-C 1-6 -alkyl, or C 3-7 -alkoxyalkyl; R 4 and R 5 are the same or different and each is hydrogen, halogen, nitro, trifluoromethyl, C 1-6 -alkyl, C 3-6 -cycloalkyl, C 1-3 -alkoxy, cyano, C 2-4 -alkoxycarbonyl or C 1-3 -alkylthio; R 6 is hydrogen, C 1-6 -alkyl, C 3-6 -cycloalkyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, phenyl-C 1-3 -alkyl optionally substituted on the phenyl ring by halogen, nitro trifluoromethyl, C 1-6 -alkyl, C 3-6 -cycloalkyl, C 1-3 -alkoxy, cyano, C 1-3 -alkylthio and C 2-4 -alkoxycarbonyl groups, or naphthyl, wherein the phenyl or naphthyl groups can be optionally substituted by one or two halogen, nitro, trifluoromethyl, C 1-6 -alkyl, C 3-6 -cycloalkyl, C 1-3 -alkoxy, cyano, C 1-3 -alkylthio and C 2-4 -alkoxycarbonyl groups; A is C 2-4 -alkylene; Ar is 2-pyridyl, 3-pyridyl, 4-pyridyl or phenyl or naphthyl which phenyl or naphthyl can be optionally substituted by one or two nitro, trifluoromethyl, halogen, C 1-6 -alkyl, C 3-6 -cycloalkyl, C 1-3 -alkoxy, cyano, C 1-3 -alkylthio and C 2-4 -alkoxycarbonyl; m is 2, and n is 1 or 2; wherein ##STR63## represents phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furyl, 2-thienyl, 2,1,3-benzoxadiazol-4-yl, or 2,1,3-benzothiadiazol-4-yl; or a pharmaceutically acceptable salt thereof.
Claim 4
Dependent Claim
227 words
A dihydropyridine compound of the formula ##STR62## wherein R 1 , R 2 and R 3 are the same or different and each is C 1-6 -alkyl, C 3-6 -cycloalkyl, C 3-6 -cycloalkyl-C 1-6 -alkyl, or C 3-7 -alkoxyalkyl; R 4 and R 5 are the same or different and each is hydrogen, halogen, nitro, trifluoromethyl, C 1-6 -alkyl, C 3-6 -cycloalkyl, C 1-3 -alkoxy, cyano, C 2-4 -alkoxycarbonyl or C 1-3 -alkylthio; R 6 is hydrogen, C 1-6 -alkyl, C 3-6 -cycloalkyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, phenyl-C 1-3 -alkyl optionally substituted on the phenyl ring by halogen, nitro trifluoromethyl, C 1-6 -alkyl, C 3-6 -cycloalkyl, C 1-3 -alkoxy, cyano, C 1-3 -alkylthio and C 2-4 -alkoxycarbonyl groups, or naphthyl, wherein the phenyl or naphthyl groups can be optionally substituted by one or two halogen, nitro, trifluoromethyl, C 1-6 -alkyl, C 3-6 -cycloalkyl, C 1-3 -alkoxy, cyano, C 1-3 -alkylthio and C 2-4 -alkoxycarbonyl groups; A is C 2-4 -alkylene; Ar is 2-pyridyl, 3-pyridyl, 4-pyridyl or phenyl or naphthyl which phenyl or naphthyl can be optionally substituted by one or two nitro, trifluoromethyl, halogen, C 1-6 -alkyl, C 3-6 -cycloalkyl, C 1-3 -alkoxy, cyano, C 1-3 -alkylthio and C 2-4 -alkoxycarbonyl; m is 2, and n is 1 or 2; wherein ##STR63## represents phenyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-furyl, 2-thienyl, 2,1,3-benzoxadiazol-4-yl, or 2,1,3-benzothiadiazol-4-yl; or a pharmaceutically acceptable salt thereof.
Claim 5
Dependent Claim
11 words
A dihydropyridine compound claimed in claim 1, wherein A is ethylene.
Claim 6
Dependent Claim
11 words
A dihydropyridine compound claimed in claim 1, wherein X is vinylene.
Claim 7
Dependent Claim
11 words
A dihydropyridine compound claimed in claim 1, wherein Ar is phenyl.
Claim 8
Dependent Claim
11 words
A dihydropyridine compound claimed in claim 1, wherein X is azomethine.
Claim 9
Dependent Claim
11 words
A dihydropyridine compound claimed in claim 1, wherein X is oxygen.
Claim 10
Dependent Claim
21 words
A dihydropyridine compound claimed in claim 1, wherein R 6 and Ar each is a phenyl group and n is 1.
Claim 11
Dependent Claim
28 words
A dihydropyridine compound claimed in claim 1, wherein R 6 and Ar each is phenyl, X is vinylene, A is ethylene, m is 2, and n is 1.
Claim 12
Dependent Claim
12 words
A dihydropyridine compound claimed in claim 1, which is 2-(4-benzhydryl-1-piperazinyl)ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.
Claim 13
Dependent Claim
12 words
A dihydropyridine compound claimed in claim 1, which is 2-[4-(4,4'-difluorobenzhydryl)-1-piperazinyl]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.
Claim 14
Dependent Claim
12 words
A dihydropyridine compound claimed in claim 1, which is 2-[4-(4,4'-dimethylbenzhydryl)-1-piperazinyl]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.
Claim 15
Dependent Claim
12 words
A dihydropyridine compound claimed in claim 1, which is 2-[4-(4,4'-dichlorobenzhydryl)-1-piperazinyl]ethyl methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.
Claim 16
Dependent Claim
12 words
A dihydropyridine compound claimed in claim 1, which is 2-(4-benzhydryl-1-piperazinyl)ethyl methyl 4-(2,1,3-benzoxadiazol-4-yl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate.
Claim 17
Dependent Claim
33 words
A pharmaceutical composition which comprises, as an active ingredient, an effective antihypertensive amount of a dihydropyridine compound or its salt as defined in claim 1, and a pharmaceutically acceptable carrier or diluent therefor.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1993-01-08 | 1993-07-10 | 1994-01-09 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1997-01-08 | 1997-07-10 | 1998-01-09 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2001-01-08 | 2001-07-10 | 2002-01-09 | $7700.00 | Window Closed / Lapsed |