US4218448A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Antihypertensive polyfluorohydroxyisopropyl bicyclic and tricyclic carbostyrils
Assignee: EIDP Inc
•
Filing: 1977-12-22
•
Granted: 1980-08-19
•
Expires: 1997-12-22
Abstract
Abstract Polyfluorohydroxyisopropyl bicyclic and tricyclic carbostyrils, such as 1,2-dihydro-8-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-6-m ethyl-4H-pyrrolo-[3,2,1-ij]quinolin-7-one, useful as antihypertensive agents.
Inventors
- 👤 Paul E. Aldrich
- 👤 Gilbert H. Berezin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 16:42
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/20; C07D215/22; C07D215/227; C07D209/00; C07D209/02; C07D209/04; C07D209/08; C07D209/56; C07D209/80; C07D209/82; C07D209/86; C07D215/12; C07D215/14; C07D219/00; C07D219/02; C07D455/00; C07D455/03; C07D455/04; C07D471/00; C07D471/02; C07D471/06
Claims Analysis
Total Claims: 74
Claim 1
Independent Claim
210 words
A compound of the formula: ##STR110## where R 1 =H or alkyl of 1-4 carbons: R 2 =H or alkyl of 1-4 carbons; provided when R 1 =alkyl, R 2 =H, --CH 3 or --CH 2 CH 3 ; or R 1 +R 2 taken together, is ##STR111## where R 6 =H or --CH 3 ; R 7 =H or --CH 3 ; R 8 =H or alkyl of 1-4 carbons; R 9 =H or alkyl of 1-4 carbons; or R 8 +R 9 , taken together, is --(CH 2 ) 4 --; provided (i) at least one of R 6 , R 7 , R 8 , or R 9 =H; and (ii) the sum of the carbons of R 6 , R 7 , R 8 , and R 9 is not more than 6; ##STR112## where R 10 =H, --CH 3 , or --CH 2 CH 3 ; R 11 =H, --CH 3 , or --CH 2 CH 3 ; R 12 =H, --CH 3 , or --CH 2 CH 3 ; or R 11 , taken together with R 10 or R 12 , is --(CH 2 ) 4 --; provided at least one of R 10 , R 11 , or R 12 =H; or
Claim 2
Dependent Claim
210 words
A compound of the formula: ##STR110## where R 1 =H or alkyl of 1-4 carbons: R 2 =H or alkyl of 1-4 carbons; provided when R 1 =alkyl, R 2 =H, --CH 3 or --CH 2 CH 3 ; or R 1 +R 2 taken together, is ##STR111## where R 6 =H or --CH 3 ; R 7 =H or --CH 3 ; R 8 =H or alkyl of 1-4 carbons; R 9 =H or alkyl of 1-4 carbons; or R 8 +R 9 , taken together, is --(CH 2 ) 4 --; provided (i) at least one of R 6 , R 7 , R 8 , or R 9 =H; and (ii) the sum of the carbons of R 6 , R 7 , R 8 , and R 9 is not more than 6; ##STR112## where R 10 =H, --CH 3 , or --CH 2 CH 3 ; R 11 =H, --CH 3 , or --CH 2 CH 3 ; R 12 =H, --CH 3 , or --CH 2 CH 3 ; or R 11 , taken together with R 10 or R 12 , is --(CH 2 ) 4 --; provided at least one of R 10 , R 11 , or R 12 =H; or
Claim 3
Dependent Claim
75 words
(c) --(CH 2 ) 4 --; R 3 =H, CH 3 , F, Cl, Br, NO 2 , NH 2 , or OH; R 4 =H or alkyl of 1-4 carbons; R 5 =H, benzyl, alkanoyl, alkenoyl, and hydrocarbon aroyl or alkyl of 1-6 carbons; Ra=CF 3 , CF 2 Cl or CF 2 H; Rb=CF 3 , CF 2 Cl or CF 2 H; and when R 5 =H, its pharmaceutical suitable metal salt.
Claim 4
Dependent Claim
75 words
(c) --(CH 2 ) 4 --; R 3 =H, CH 3 , F, Cl, Br, NO 2 , NH 2 , or OH; R 4 =H or alkyl of 1-4 carbons; R 5 =H, benzyl, alkanoyl, alkenoyl, and hydrocarbon aroyl or alkyl of 1-6 carbons; Ra=CF 3 , CF 2 Cl or CF 2 H; Rb=CF 3 , CF 2 Cl or CF 2 H; and when R 5 =H, its pharmaceutical suitable metal salt.
Claim 5
Dependent Claim
10 words
The compound of claim 1 where R 3 is hydrogen.
Claim 6
Dependent Claim
12 words
The compound of claim 1 where R 4 is methyl or ethyl.
Claim 7
Dependent Claim
10 words
The compound of claim 1 where R 5 is hydrogen.
Claim 8
Dependent Claim
16 words
The compound of claim 1 where R 1 and R 2 , taken together, are: ##STR113##
Claim 9
Dependent Claim
28 words
The compound of claim 5 where R 1 and R 2 , taken together, are: ##STR114## and R 6 , R 7 , and R 8 are hydrogen.
Claim 10
Dependent Claim
24 words
The compound of claim 5 where R 1 and R 2 , taken together, are: ##STR115## and R 10 and R 11 are hydrogen.
Claim 11
Dependent Claim
17 words
The compound of claim 6 where R 3 is hydrogen and R 4 is methyl or ethyl.
Claim 12
Dependent Claim
17 words
The compound of claim 7 where R 3 is hydrogen and R 4 is methyl or ethyl.
Claim 13
Dependent Claim
10 words
The compound of claim 8 where R 5 is hydrogen.
Claim 14
Dependent Claim
10 words
The compound of claim 9 where R 5 is hydrogen.
Claim 15
Dependent Claim
23 words
The compound of claim 8 where Ra is CF 3 and Rb is CF 3 , CF 2 Cl or CF 2 H.
Claim 16
Dependent Claim
23 words
The compound of claim 9 where Ra is CF 3 and Rb is CF 3 , CF 2 Cl or CF 2 Cl.
Claim 17
Dependent Claim
14 words
The compound of claim 1 where Ra and Rb both are CF 3 .
Claim 18
Dependent Claim
6 words
The compound of claim 1: 2,3-dihydro-9-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-7-methyl-1H,5H-benzo[ij]quinolizin-5-one.
Claim 19
Dependent Claim
5 words
The compound of claim 1:
Claim 20
Dependent Claim
1 words
3-dihydro-3,7-dimethyl-9-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-1H,5H-benzo[ij]quinolizin-5-one.
Claim 21
Dependent Claim
1 words
3-dihydro-3,7-dimethyl-9-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-1H,5H-benzo[ij]quinolizin-5-one.
Claim 22
Dependent Claim
6 words
The compound of claim 1: 2,3-dihydro-7ethyl-9-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-1H,5H-benzo[ij]quinolizin-5-one.
Claim 23
Dependent Claim
6 words
The compound of claim 1: 1,2-dihydro-8-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-6-methyl-4H-pyrrolo[3,2,1-ij]quinolin-4-one.
Claim 24
Dependent Claim
6 words
The compound of claim 1: 1,2-dihydro-2,6-dimethyl-8-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-4H-pyrrolo[3,2,1-ij]quinolin-4-one.
Claim 25
Dependent Claim
6 words
The compound of claim 1: 1,2-dihydro-6-ethyl-8-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-4H-pyrrolo[3,2,1-ij]quinolin-4-one.
Claim 26
Dependent Claim
6 words
The compound of claim 1: 1,2-dihydro-8-[2,2-difluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-6-methyl-4H-pyrrolo[3,2,1-ij]quinolin-4-one.
Claim 27
Dependent Claim
6 words
The compound of claim 1: 1,2-dihydro-8-[2-chloro-2,2-difluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-6-methyl-4H-pyrrolo[3,2,1-ij]quinolin-4-one.
Claim 28
Dependent Claim
6 words
The compound of claim 1: 1,2-dihydro-8-[2,2-difluoro-1-hydroxy-1-(difluoromethyl)ethyl]-6-methyl-4H-pyrrolo[3,2,1-ij]quinolin-4-one.
Claim 29
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier and an effective antihypertensive amount of a compound of claim 1.
Claim 30
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier and an effective antihypertensive amount of a compound of claim 2.
Claim 31
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier and an effective antihypertensive amount of a compound of claim 3.
Claim 32
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier and an effective antihypertensive amount of a compound of claim 4.
Claim 33
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier and an effective antihypertensive amount of a compound of claim 5.
Claim 34
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier and an effective antihypertensive amount of a compound of claim 6.
Claim 35
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier and an effective antihypertensive amount of a compound of claim 7.
Claim 36
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier and an effective antihypertensive amount of a compound of claim 8.
Claim 37
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier and an effective antihypertensive amount of a compound of claim 9.
Claim 38
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier and an effective antihypertensive amount of a compound of claim 10.
Claim 39
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier and an effective antihypertensive amount of a compound of claim 11.
Claim 40
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier and an effective antihypertensive amount of a compound of claim 12.
Claim 41
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier and an effective antihypertensive amount of a compound of claim 13.
Claim 42
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier of an effective antihypertensive amount of a compound of claim 14.
Claim 43
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier of an effective antihypertensive amount of the compound of claim 15.
Claim 44
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier of an effective antihypertensive amount of the compound of claim 16.
Claim 45
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier of an effective antihypertensive amount of the compound of claim 17.
Claim 46
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier of an effective antihypertensive amount of the compound of claim 18.
Claim 47
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier of an effective antihypertensive amount of the compound of claim 19.
Claim 48
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier of an effective antihypertensive amount of the compound of claim 20.
Claim 49
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier of an effective antihypertensive amount of the compound of claim 21.
Claim 50
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier of an effective antihypertensive amount of the compound of claim 22.
Claim 51
Dependent Claim
19 words
A pharmaceutical composition comprising a pharmaceutically suitable carrier of an effective antihypertensive amount of the compound of claim 23.
Claim 52
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of a compound of claim 1.
Claim 53
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of a compound of claim 2.
Claim 54
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of a compound of claim 3.
Claim 55
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of a compound of claim 4.
Claim 56
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of a compound of claim 5.
Claim 57
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of a compound of claim 6.
Claim 58
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of a compound of claim 7.
Claim 59
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of a compound of claim 8.
Claim 60
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of a compound of claim 9.
Claim 61
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of a compound of claim 10.
Claim 62
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of a compound of claim 11.
Claim 63
Dependent Claim
24 words
A method of treating hypertension in a mammel which comprises administering to the mammal an effective antihypertensive amount of a compound of claim 12.
Claim 64
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of a compound of claim 13.
Claim 65
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of a compound of claim 14.
Claim 66
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of the compound of claim 15.
Claim 67
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of the compound of claim 16.
Claim 68
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of the compound of claim 17.
Claim 69
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of the compound of claim 18.
Claim 70
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of the compound of claim 19.
Claim 71
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of the compound of claim 20.
Claim 72
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of the compound of claim 21.
Claim 73
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of the compound of claim 22.
Claim 74
Dependent Claim
24 words
A method of treating hypertension in a mammal which comprises administering to the mammal an effective antihypertensive amount of the compound of claim 23.
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) | 1983-08-19 | 1984-02-18 | 1984-08-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-08-19 | 1988-02-18 | 1988-08-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-08-19 | 1992-02-18 | 1992-08-19 | $7700.00 | Window Closed / Lapsed |