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US4686226A
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Substituted benzo[b]furo- and benzo[b]thieno quinolizines
Assignee: Merck and Co Inc
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Filing: 1985-09-03
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Granted: 1987-08-11
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Expires: 2005-09-03
Abstract
Abstract Substituted hexahydro arylquinolizines and pharmaceutically acceptable salts thereof are selective alpha 2-adrenergic receptor antagonists and thereby useful as antidepressants, antihypertensives, ocular antihypertensives, antidiabetics, antiobesity and platelet aggregation inhibitors and modifiers of gastrointestinal motility.
Inventors
- 👤 Joel R. Huff
- 👤 John J. Baldwin
- 👤 Yojiro Sakurai
- 👤 Joseph P. Vacca
- 👤 James P. Guare, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 16:49
CPC Classifications
C; C07; C07D; C07D471/00; C07D471/12; C07D471/14; A; A61; A61P; A61P1/00; A61P25/00; A61P25/02; A61P25/24; A61P25/26; A61P3/00; A61P3/04; A61P3/08; A61P7/00; A61P7/02; A61P9/00; A61P9/12; C07D455/00; C07D455/03; C07D455/04; C07D455/06; C07D491/00; C07D491/12; C07D491/14; C07D495/00; C07D495/12; C07D495/14
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
199 words
A compound of structural formula: ##STR40## or a pharmaceutically acceptable salt thereof wherein Ar represents an aromatic group selected from X,Y-benzo[b]furo-, X,Y-benzo[b]thieno-, and; wherein X and Y are independently: (1) hydrogen, (2) halo, (3) hydroxy, (4) C 1-3 alkoxy, or (5) C 1-6 alkyl; R is (1) ##STR41## wherein R 1 is hydrogen or C 1-5 alkyl, either straight or branched chain; (2) ##STR42## wherein R 2 is (a) hydrogen, (b) C 1-5 alkyl, or (c) C 1-5 alkylidene; (3) ##STR43## (4) ##STR44## wherein R 1 and R 2 can be joined together to form pyrrolidine or piperidine; (5) ##STR45## wherein Q is (a) O, or (b) N--OR 1 ; (6) ##STR46## wherein Z is (a) --OR 3 or --SR 3 (b) --NR 2 R 3 , wherein R 3 is (i) H, (ii) C 1-5 alkyl, unsubstituted or substituted with (1) --OH (2) --COOR 1 , (3) --SO 2 R 2 , (4) --N(R 2 )SO 2 R 2 , (iii) --COOR 2 , (iv) --SO 2 R 2 , (v) SO 2 NR 1 R 2 ; R 4 is (a) C 1-5 alkyl, or (b) C 1-5 alkylidene; and the broken lines represent possible double bonds.
Claim 2
Dependent Claim
199 words
A compound of structural formula: ##STR40## or a pharmaceutically acceptable salt thereof wherein Ar represents an aromatic group selected from X,Y-benzo[b]furo-, X,Y-benzo[b]thieno-, and; wherein X and Y are independently: (1) hydrogen, (2) halo, (3) hydroxy, (4) C 1-3 alkoxy, or (5) C 1-6 alkyl; R is (1) ##STR41## wherein R 1 is hydrogen or C 1-5 alkyl, either straight or branched chain; (2) ##STR42## wherein R 2 is (a) hydrogen, (b) C 1-5 alkyl, or (c) C 1-5 alkylidene; (3) ##STR43## (4) ##STR44## wherein R 1 and R 2 can be joined together to form pyrrolidine or piperidine; (5) ##STR45## wherein Q is (a) O, or (b) N--OR 1 ; (6) ##STR46## wherein Z is (a) --OR 3 or --SR 3 (b) --NR 2 R 3 , wherein R 3 is (i) H, (ii) C 1-5 alkyl, unsubstituted or substituted with (1) --OH (2) --COOR 1 , (3) --SO 2 R 2 , (4) --N(R 2 )SO 2 R 2 , (iii) --COOR 2 , (iv) --SO 2 R 2 , (v) SO 2 NR 1 R 2 ; R 4 is (a) C 1-5 alkyl, or (b) C 1-5 alkylidene; and the broken lines represent possible double bonds.
Claim 3
Dependent Claim
9 words
The compound of claim 1, wherein Ar is benzo[b]furo--.
Claim 4
Dependent Claim
65 words
The compound of claim 2, wherein R is CH 2 CO 2 R 1 , CH 3 CHCO 2 R 1 , R 1 --C═NOR 3 , R 1 (R 4 )C--OH, R 1 CHO(CH 2 ) 2 OH, or R 1 (R 4 )CO(CH 2 ) 2 OH wherein R 1 , R 3 and R 4 are independently C 1-5 alkyl or H.
Claim 5
Dependent Claim
19 words
The compound of claim 3, wherein R 1 , and R 4 are methyl and R 3 is H.
Claim 6
Dependent Claim
22 words
A pharmaceutical composition for the treatment of depression, comprising a pharmaceutical carrier and an effective amount of the compound of claim 1.
Claim 7
Dependent Claim
10 words
The composition of claim 5 wherein the Ar is benzo[b]furo--.
Claim 8
Dependent Claim
65 words
The composition of claim 6, wherein R is --CH 2 CO 2 R 1 , CH 3 CHCO 2 R 1 , R 1 --C═NOR 3 , R 1 (R 4 )C--OH, R 1 CH--O(CH 2 ) 2 OH or R 1 (R 4 )C--O(CH 2 ) 2 OH wherein R 1 , R 3 and R 4 are independently C 1-5 alkyl or H.
Claim 9
Dependent Claim
18 words
The composition of claim 7 wherein R 1 and R 4 are methyl and R 3 is H.
Claim 10
Dependent Claim
29 words
A method of treating depression which comprises the administration to a patient in need of such treatment of an effective amount of a compound as described in claim 1.
Claim 11
Dependent Claim
9 words
The method of claim 9 wherein Ar is benzo[b]furo--.
Claim 12
Dependent Claim
65 words
The method of claim 10, wherein R is --CH 2 CO 2 R 1 , CH 3 CHCO 2 R 1 , R 1 --C═NOR 3 , R 1 (R 4 )--C--OH, R 1 CHO(CH 2 ) 2 OH, or R 1 (R 4 )C--O(CH 2 ) 2 OH wherein R 1 , R 3 and R 4 are indepenently C 1-5 alkyl or H.
Claim 13
Dependent Claim
18 words
The method of claim 11, wherein R 1 and R 4 are methyl and R 3 is H.
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) | 1990-08-10 | 1991-02-09 | 1991-08-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-08-10 | 1995-02-09 | 1995-08-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-08-10 | 1999-02-09 | 1999-08-11 | $7700.00 | Window Closed / Lapsed |