US4555509A
Expired / Lapsed
US
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Anti-hypertensive benzo[b]pyran-3-ols
Assignee: BEEHAM GROUP PLC
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Filing: 1984-03-22
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Granted: 1985-11-26
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Expires: 2004-03-22
Abstract
Abstract Compounds of the formula (I): ##STR1## wherein: one of R 1 and R 2 is hydrogen and the other is C 1-6 alkyl-thiocarbonyl, C 1-6 alkoxy thiocarbonyl, C 1-6 alkyl-thiocarbonyloxy, 1-mercapto C 2-7 alkyl or formyl; one of R 3 and R 4 is hydrogen or C 1-4 alkyl and the other is C 1-4 alkyl, or R 3 and R 4 together with the carbon atom to which they are attached are C 3-6 spiroalkyl; R 5 is hydrogen, C 1-3 alkyl or C 1-8 acyl; and n is 1 or 2; the lactam group being trans to the OR 5 group, having anti-hypertensive activity.
Inventors
- 👤 John M. Evans
- 👤 Robin E. Buckingham
- 👤 Kenneth Willcocks
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 08:58
CPC Classifications
C; C07; C07D; C07D405/00; C07D405/02; C07D405/04; A; A61; A61P; A61P9/00; A61P9/12
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
102 words
A compound of formula (I): ##STR18## wherein: one of R 1 and R 2 is hydrogen and the other is C 1-6 alkyl-thiocarbonyl, C 1-6 alkoxy-thiocarbonyl, C 1-6 alkyl-thiocarbonyloxy, 1-mercapto C 2-7 alkyl or formyl; one of R 3 and R 4 is hydrogen or C 1-4 alkyl and the other is C 1-4 alkyl, or R 3 and R 4 together with the carbon atom to which they are attached are C 3-6 spiroalkyl; R 5 is hydrogen, C 1-3 alkyl or C 1-8 acyl; and n is 1 or 2; the lactam group being trans to the OR 5 group.
Claim 2
Dependent Claim
102 words
A compound of formula (I): ##STR18## wherein: one of R 1 and R 2 is hydrogen and the other is C 1-6 alkyl-thiocarbonyl, C 1-6 alkoxy-thiocarbonyl, C 1-6 alkyl-thiocarbonyloxy, 1-mercapto C 2-7 alkyl or formyl; one of R 3 and R 4 is hydrogen or C 1-4 alkyl and the other is C 1-4 alkyl, or R 3 and R 4 together with the carbon atom to which they are attached are C 3-6 spiroalkyl; R 5 is hydrogen, C 1-3 alkyl or C 1-8 acyl; and n is 1 or 2; the lactam group being trans to the OR 5 group.
Claim 3
Dependent Claim
24 words
A compound according to claim 1, wherein the other of R 1 and R 2 is C 1-6 alkyl-thiocarbonyl, C 1-6 alkoxy-thiocarbonyl or formyl.
Claim 4
Dependent Claim
18 words
A compound according to claim 1, wherein the alkyl moieties of the alkyl-containing groups are methyl or ethyl.
Claim 5
Dependent Claim
11 words
A compound according to claim 1, wherein R 2 is hydrogen.
Claim 6
Dependent Claim
17 words
A compound according to claim 1, wherein R 3 and R 4 are both methyl or ethyl.
Claim 7
Dependent Claim
11 words
A compound according to claim 1, wherein R 5 is hydrogen.
Claim 8
Dependent Claim
3 words
6-Formyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-pyrrolidinyl)-2H-benzo[b]pyran-3-ol or 6-formyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-piperidinyl)-2H-benzo[b]pyran-3-ol.
Claim 9
Dependent Claim
3 words
6-Formyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-pyrrolidinyl)-2H-benzo[b]pyran-3-ol or 6-formyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-piperidinyl)-2H-benzo[b]pyran-3-ol.
Claim 10
Dependent Claim
5 words
6-Thioacetyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-pyrrolidinyl)-2H-benzo[b]pyran-3-ol; 6-thioacetyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-piperidinyl)-2H-benzo[b]pyran-3-ol; 6-methoxy-thiocarbonyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-pyrrolidinyl)-2H-benzo[b]pyran-3-ol; or 6-methoxy-thiocarbonyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-piperidinyl)-2H-benzo[b]pyran-3-ol.
Claim 11
Dependent Claim
5 words
6-Thioacetyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-pyrrolidinyl)-2H-benzo[b]pyran-3-ol; 6-thioacetyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-piperidinyl)-2H-benzo[b]pyran-3-ol; 6-methoxy-thiocarbonyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-pyrrolidinyl)-2H-benzo[b]pyran-3-ol; or 6-methoxy-thiocarbonyl-3,4-dihydro-2,2-dimethyl-trans-4-(2-oxo-1-piperidinyl)-2H-benzo[b]pyran-3-ol.
Claim 12
Dependent Claim
30 words
A pharmaceutical composition for treating or preventing hypertension in animals including humans which comprises an anti-hypertensive effective amount of a compound according to claim 1 and a pharmaceutically acceptable carrier.
Claim 13
Dependent Claim
28 words
A method of treating or preventing hypertension in animals including humans which comprises administering to the patient an anti-hypertensive effective amount of a compound according to claim 1.
Claim 14
Dependent Claim
176 words
A compound of formula (XV): ##STR19## wherein one of the R 1 ' and R 2 ' is hydrogen or a group or atom convertible into hydrogen and the other is C 1-6 alkyl-thiocarbonyl, C 1-6 alkoxy-thiocarbonyl, C 1-6 alkyl-thiocarbonyloxy, 1-mercapto C 2-7 alkyl or formyl or a group or atom convertible thereto, R 3 and R 4 are as defined in claim 1 and R 7 is OR 5 , in which R 5 is as defined in claim 1, and R 8 is --NH(CH 2 ) n+2 COL 1 , --NH 2 , --N 3 , ##STR20## --HN(CH 2 ) n+2 CH(OR 6 ) 2 or --HNCO(CH 2 ) n+2 L 3 , in which n is as defined in claim 1, L 1 is hydroxy or C 1-4 alkoxy, L 3 is chloro, and R 6 is C 1-4 alkyl, or R 7 is bromo and R 8 is hydroxy, or R 7 and R 8 together are oxygen; R 7 , when OR 5 or bromo, being trans to R 8 .
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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) | 1988-11-25 | 1989-05-27 | 1989-11-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-11-25 | 1993-05-27 | 1993-11-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-11-25 | 1997-05-27 | 1997-11-26 | $7700.00 | Window Closed / Lapsed |