Patent US4747195A successfully refreshed from Google Patents.
US4640920A
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US
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4-(cinnolinylamino or quinazolinylamino)benzenesulphonamides and intermediates therefor
Assignee: John Wyeth and Brother Ltd
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Filing: 1985-06-13
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Granted: 1987-02-03
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Expires: 2005-06-13
Abstract
Abstract Novel quinazoline and cinnoline derivatives having the formula ##STR1## (wherein one of A and B is CH and the other one of A and B is N; X 1 is halogen or CF 3 and X 3 is one of the groups II, III, IV or V ##STR2## where Q is lower alkylene; R 1 is hydrogen or lower alkyl; R 2 and R 3 are independently lower alkyl or R 2 and R 3 are a divalent radical such that HNR 2 R 3 is a secondary cyclic amine with 5 to 7 ring atoms; R 4 is lower alkyl; n is 0 or 1; the rings shown in formulae III and IV are piperidine or pyrrolidine optionally substituted by lower alkyl; and the ring shown in formula V is piperazine optionally substituted by lower alkyl) and their pharmaceutically acceptable salts are useful as pharmaceuticals particularly as anti-hypertensives. Novel intermediates are also described including the corresponding sulphonic acids of formula I (where A, B and X 1 are defined above and X 3 is OH).
Inventors
- 👤 John T. A. Boyle
- 👤 Richard S. Todd
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 15:59
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/12; C07D207/00; C07D207/02; C07D207/04; C07D207/08; C07D207/09; C07D215/00; C07D215/02; C07D215/16; C07D215/38; C07D215/42; C07D215/44; C07D237/00; C07D237/26; C07D237/28; C07D239/00; C07D239/70; C07D239/72; C07D239/86; C07D239/94; C07D403/00; C07D403/02; C07D403/12
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
189 words
A compound selected from those having the formula I ##STR23## and their pharmaceutically acceptable salts, wherein one of A and B is CH whilst the other one of A and B is N; X 1 is selected from halogen and trifluoromethyl and X 3 is a group having one of the formulae II, III, IV ##STR24## wherein Q is lower alkylene; R 1 is hydrogen or lower alkyl; R 2 and R 3 , when separate, are independently lower alkyl and R 2 and R 3 , when linked together, represent a divalent radical such that HNR 2 R 3 is a secondary cyclic amine with 5 to 7 ring atoms; R 4 is lower alkyl; n is selected from 0 and 1; the ring illustrated in formulae III and IV is selected from the group consisting of piperidine, pyrrolidine, piperidine substituted on at least one ring carbon atom by lower alkyl and pyrrolidine substituted on at least one ring carbon atom by lower alkyl and the ring illustrated in formula V is selected from piperazine and piperazine substituted on at least one ring carbon atom by lower alkyl.
Claim 2
Dependent Claim
189 words
A compound selected from those having the formula I ##STR23## and their pharmaceutically acceptable salts, wherein one of A and B is CH whilst the other one of A and B is N; X 1 is selected from halogen and trifluoromethyl and X 3 is a group having one of the formulae II, III, IV ##STR24## wherein Q is lower alkylene; R 1 is hydrogen or lower alkyl; R 2 and R 3 , when separate, are independently lower alkyl and R 2 and R 3 , when linked together, represent a divalent radical such that HNR 2 R 3 is a secondary cyclic amine with 5 to 7 ring atoms; R 4 is lower alkyl; n is selected from 0 and 1; the ring illustrated in formulae III and IV is selected from the group consisting of piperidine, pyrrolidine, piperidine substituted on at least one ring carbon atom by lower alkyl and pyrrolidine substituted on at least one ring carbon atom by lower alkyl and the ring illustrated in formula V is selected from piperazine and piperazine substituted on at least one ring carbon atom by lower alkyl.
Claim 3
Dependent Claim
21 words
A compound as claimed in claim 1, wherein X 1 is at the 7-position of the quinazoline or cinnoline ring system.
Claim 4
Dependent Claim
57 words
A compound as claimed in claim 1, wherein X 3 is a group having one of the formulae IIa and IVa ##STR25## wherein Q is alkylene of 1 to 4 carbon atoms; R 2 , R 3 and R 4 are independently alkyl of 1 to 4 carbon atoms and m is selected from 0 and 1.
Claim 5
Dependent Claim
16 words
A compound as claimed in claim 1, which is 4-(7-Chloro-4-quinazolinylamino)-N-(2-diethylaminoethyl)-benzenesulphonamide or a pharmaceutically acceptable salt thereof.
Claim 6
Dependent Claim
16 words
A compound as claimed in claim 1, which is 4-(7-Chloro-4-cinnolinylamino)-N-(2-diethylaminoethyl)-benzenesulphonamide or a pharmaceutically acceptable salt thereof.
Claim 7
Dependent Claim
16 words
A compound as claimed in claim 1, which is 4-(6-Chloro-4-quinazolinylamino)-N-(2-diethylaminoethyl)-benzenesulphonamide or a pharmaceutically acceptable salt thereof.
Claim 8
Dependent Claim
16 words
A compound as claimed in claim 1, which is 4-[7-Chloro-4-quinazolinylamino]-N-(1-ethyl-3-piperidyl)-benzenesulphonamide or a pharmaceutically acceptable salt thereof.
Claim 9
Dependent Claim
16 words
A compound as claimed in claim 1, which is 4-[7-Chloro-4-cinnolinylamino]-N-(1-ethyl-3-piperidyl)-benzenesulphonamide or a pharmaceutically acceptable salt thereof.
Claim 10
Dependent Claim
16 words
A compound as claimed in claim 1, which is 1-[4-(7-Chloro-4-quinazolinylamino)benzenesulphonyl]-4-methylpiperazine or a pharmaceutically acceptable salt thereof.
Claim 11
Dependent Claim
17 words
A compound as claimed in claim 1, which is 4-(7-Chloro-4-quinazolinylamino)-N-[2-(1-pyrrolidinyl) ethyl]benzenesulphonamide or a pharmaceutically acceptable salt thereof.
Claim 12
Dependent Claim
16 words
A compound as claimed in claim 1, which is 4-(7-Chloro-4-quinazolinylamino)-N-[(2-(1-ethyl)-pyrrolidinyl)methyl]benzenesulphonamide or a pharmaceutically acceptable salt thereof.
Claim 13
Dependent Claim
16 words
A compound as claimed in claim 1, which is 4-(7-Chloro-4-quinazolinylamino)-N-(3-diethylaminopropyl)-benzenesulphonamide or a pharmaceutically acceptable salt thereof.
Claim 14
Dependent Claim
16 words
A compound as claimed in claim 1, which is N-[2-diethylaminoethyl]-4-[7-trifluoromethyl-4-quinazolinylamino]benzenesulphonamide or a pharmaceutically acceptable salt thereof.
Claim 15
Dependent Claim
25 words
A pharmaceutical composition comprising an anti-hypertensively effective amount of a compound as claimed in claim 1 in association or combination with a pharmaceutically acceptable carrier.
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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) | 1990-02-02 | 1990-08-04 | 1991-02-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-02-02 | 1994-08-04 | 1995-02-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-02-02 | 1998-08-04 | 1999-02-03 | $7700.00 | Window Closed / Lapsed |