Patent US3145252A successfully refreshed from Google Patents.
Patent US4595690A successfully refreshed from Google Patents.
US4595690A
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Antihypertensive dihydropyridine derivatives
Assignee: Syntex USA LLC
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Filing: 1985-02-11
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Granted: 1986-06-17
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Expires: 2005-02-11
Abstract
Abstract Novel dihydropyridine derivatives which are useful for treating congestive heart failure, hypertension, and angina have the formula 1: <IMAGE> (1) or a pharmaceutically acceptable acid addition salt thereof, wherein: n is an integer from 0 to 8; Y is -O, -NH, -NR2, -S, -S(O), -S(O)2, or a bond; R1 and R2 are each independently A1, A2, A3 or A4 where: A1 is -(CH2)m(CHOH)pCH2OH; A2 is -(CH2)qCH(3-r)[(CH2)sOH]r; A3 is -(CH2)qCH(3-r)[(CH2)pCOOR3]r; and A4 is -(CH2)mCOOR3; where: m is an integer from 1 to 8; p is an integer from 0 to 4; q is an integer from 0 to 8; r is 2 or 3; s is an integer from 1 to 4; and R3 is H or alkyl of 1 to 18 carbon atoms; R4 is -NO2, -CF3, or halo; and R5 is lower alkyl or -CH2CH2OCH3.
Inventors
- 👤 Robin Clark
- 👤 Moysey M. Povzhitkov
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 23:26
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/12; A; A61; A61P; A61P9/00; A61P9/12; C07D211/00; C07D211/04; C07D211/80; C07D211/84; C07D211/90; C07D317/00; C07D317/08; C07D317/10; C07D317/14; C07D317/18; C07D317/20; C07D317/22; C07D317/24; C07D317/30
Claims Analysis
Total Claims: 25
Claim 1
Independent Claim
189 words
A compound of the formula ##STR6## or a pharmaceutically acceptable acid addition salt thereof, wherein: n is an integer from 0 to 8; Y is --O, --NH, --NR 2 , --S, --S(O), --S(O) 2 , or a bond; R 1 and R 2 are each independently A 1 , A 2 , A 3 or A 4 where A 1 is --(CH 2 ) m (CHOH) p CH 2 OH; A 2 is --(CH 2 ) q CH.sub.(3-r) [(CH 2 ) s OH] r ; A 3 is --(CH 2 ) q CH.sub.(3-r) [(CH 2 ) p COOR 3 ] r ; and A 4 is --(CH 2 ) m COOR 3 ; where m is an integer from 1 to 8; p is an integer from 0 to 4; q is an integer from 0 to 8; r is 2 or 3; s is an integer from 1 to 4; and R 3 is H or alkyl of 1 to 18 carbon atoms; R 4 is --NO 2 , --CF 3 , or halo; and R 5 is lower alkyl or --CH 2 CH 2 OCH 3 .
Claim 2
Dependent Claim
189 words
A compound of the formula ##STR6## or a pharmaceutically acceptable acid addition salt thereof, wherein: n is an integer from 0 to 8; Y is --O, --NH, --NR 2 , --S, --S(O), --S(O) 2 , or a bond; R 1 and R 2 are each independently A 1 , A 2 , A 3 or A 4 where A 1 is --(CH 2 ) m (CHOH) p CH 2 OH; A 2 is --(CH 2 ) q CH.sub.(3-r) [(CH 2 ) s OH] r ; A 3 is --(CH 2 ) q CH.sub.(3-r) [(CH 2 ) p COOR 3 ] r ; and A 4 is --(CH 2 ) m COOR 3 ; where m is an integer from 1 to 8; p is an integer from 0 to 4; q is an integer from 0 to 8; r is 2 or 3; s is an integer from 1 to 4; and R 3 is H or alkyl of 1 to 18 carbon atoms; R 4 is --NO 2 , --CF 3 , or halo; and R 5 is lower alkyl or --CH 2 CH 2 OCH 3 .
Claim 3
Dependent Claim
11 words
The compound of claim 1 wherein R 4 is meta nitro.
Claim 4
Dependent Claim
10 words
The compound of claim 2 wherein R 5 is methyl.
Claim 5
Dependent Claim
17 words
The compound of claim 3 wherein Y is para --O and R 1 is A 1 .
Claim 6
Dependent Claim
13 words
The compound of claim 4 wherein m is 1 and p is 1.
Claim 7
Dependent Claim
13 words
The compound of claim 5 wherein n is 2, i.e., the compound 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2,3-dihydroxypropoxy)phenyl]ethoxycarbonyl)-1,4-dihydropyridine.
Claim 8
Dependent Claim
13 words
The compound of claim 5 wherein n is 1, i.e., the compound 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-[4-(2,3-dihydroxypropoxy)phenyl]methoxycarbonyl)-1,4-dihydropyridine.
Claim 9
Dependent Claim
13 words
The compound of claim 5 wherein n is 3, i.e., the compound 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(3-[4-(2,3-dihydroxypropoxy)phenyl]propoxycarbonyl)-1,4-dihydropyridine.
Claim 10
Dependent Claim
20 words
The compound of claim 3 wherein n is 2, Y is para --O and R 1 is A 2 .
Claim 11
Dependent Claim
20 words
The compound of claim 9 wherein q is 0, r is 2, and s is 1, i.e., the compound 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(1,3-dihydroxyprop-2-oxy)phenyl]ethoxycarbonyl)-1,4-dihydropyridine.
Claim 12
Dependent Claim
20 words
The compound of claim 3 wherein n is 2, Y is para --NH and R 1 is A 1 .
Claim 13
Dependent Claim
18 words
The compound of claim 11 wherein m is 1, and p is 0, i.e., the compound 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2-hydroxyethylamino)phenyl]ethoxycarbonyl)-1,4-dihydropyridine hydrochloride.
Claim 14
Dependent Claim
25 words
The compound of claim 3 wherein n is 2, Y is para --NR 2 , and R 1 and R 2 are A 1 .
Claim 15
Dependent Claim
18 words
The compound of claim 13 wherein m is 1, and p is 0, i.e, the compound 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-[N,N-bis(2-hydroxyethyl)amino]phenyl]-ethoxycarbonyl)-1,4-dihydropyridine hydrochloride.
Claim 16
Independent Claim
209 words
A method for treating hypertension, congestive heart failure, angina, migraine, and vasospastic disorders which comprises administering a therapeutically effective amount of a compound of formula ##STR7## or a pharmaceutically acceptable acid addition salt thereof, wherein: n is an integer from 0 to 8; Y is --O, --NH, --NR 2 , --S, --S(O), --S(O) 2 , or a bond; R 1 and R 2 are each independently A 1 , A 2 , A 3 or A 4 where: A 1 is --(CH 2 ) m (CHOH) p CH 2 OH; A 2 is --(CH 2 ) q CH.sub.(3-r) [(CH 2 ) s OH] r ; A 3 is --(CH 2 ) q CH.sub.(3-r) [(CH 2 ) p COOR 3 ] r ; and A 4 is --(CH 2 ) m COOR 3 ; where m is an integer from 1 to 8; p is an integer from 0 to 4; q is an integer from 0 to 8; r is 2 or 3; s is an integer from 1 to 4; and R 3 is H or alkyl of 1 to 18 carbon atoms; R 4 is --NO 2 , --CF 3 , or halo; and R 5 is lower alkyl or --CH 2 CH 2 OCH 3 .
Claim 17
Independent Claim
209 words
A method for treating hypertension, congestive heart failure, angina, migraine, and vasospastic disorders which comprises administering a therapeutically effective amount of a compound of formula ##STR7## or a pharmaceutically acceptable acid addition salt thereof, wherein: n is an integer from 0 to 8; Y is --O, --NH, --NR 2 , --S, --S(O), --S(O) 2 , or a bond; R 1 and R 2 are each independently A 1 , A 2 , A 3 or A 4 where: A 1 is --(CH 2 ) m (CHOH) p CH 2 OH; A 2 is --(CH 2 ) q CH.sub.(3-r) [(CH 2 ) s OH] r ; A 3 is --(CH 2 ) q CH.sub.(3-r) [(CH 2 ) p COOR 3 ] r ; and A 4 is --(CH 2 ) m COOR 3 ; where m is an integer from 1 to 8; p is an integer from 0 to 4; q is an integer from 0 to 8; r is 2 or 3; s is an integer from 1 to 4; and R 3 is H or alkyl of 1 to 18 carbon atoms; R 4 is --NO 2 , --CF 3 , or halo; and R 5 is lower alkyl or --CH 2 CH 2 OCH 3 .
Claim 18
Dependent Claim
10 words
The method of claim 15 wherein the compound is 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2,3-dihydroxypropoxy)phenyl]ethoxycarbonyl)-1,4-dihydropyridine.
Claim 19
Dependent Claim
10 words
The method of claim 15 wherein the compound is 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-[4-(2,3-dihydroxypropoxy)phenyl]methoxycarbonyl)-1,4-dihydropyridine.
Claim 20
Dependent Claim
10 words
The method of claim 15 wherein the compound is 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(3-[4-(2,3-dihydroxypropoxy)phenyl]propoxycarbonyl)-1,4-dihydropyridine.
Claim 21
Dependent Claim
10 words
The method of claim 15 wherein the compound is 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(1,3-dihydroxyprop-2-oxy)phenyl]ethoxycarbonyl)-1,4-dihydropyridine.
Claim 22
Dependent Claim
11 words
The method of claim 15 wherein the compound is 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-(2-hydroxyethylamino)phenyl]ethoxycarbonyl)-1,4-dihydropyridine hydrochloride.
Claim 23
Dependent Claim
11 words
The method of claim 15 wherein the compound is 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-(2-[4-N,N-(2-hydroxyethyl)aminophenyl]ethoxycarbonyl)-1,4-dihydropyridine hydrochloride.
Claim 24
Dependent Claim
10 words
The method of claim 15 wherein the compound is 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-[2-(4-methoxycarbonylmethoxyphenyl)ethoxycarbonyl]-1,4-dihydropyridine.
Claim 25
Dependent Claim
11 words
The method of claim 15 wherein the compound is 2,6-dimethyl-3-methoxycarbonyl-4-(3-nitrophenyl)-5-[2-(4-aminophenyl)ethoxycarbonyl]-1,4-dihydropyridine hydrochloride.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-06-16 | 1989-12-16 | 1990-06-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-06-16 | 1993-12-16 | 1994-06-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-06-16 | 1997-12-16 | 1998-06-17 | $7700.00 | Window Closed / Lapsed |