US4435405A
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Quinoline derivatives which are 5-hydroxytryptamine antagonists
Assignee: Imperial Chemical Industries Ltd
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Filing: 1982-05-26
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Granted: 1984-03-06
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Expires: 2002-05-26
Abstract
Abstract Compounds of the formula: <IMAGE> wherein A stands for the radical -(CH2)2- which may bear one or two defined substituents; R1 stands for a (3-4C) alkyl or cyclopropyl radical, or a phenyl radical which may optionally bear one or two defined substituents, or a heteroaryl radical of five or six ring atoms which may optionally bear a (1-3C)alkyl substituent; R2 and R3 stand for hydrogen or a (1-2C)alkyl radical, or R2 stands for a (2-4C)alkylene radical which is linked to one of the carbon atoms forming the two-carbon-atom-backbone of A so as to form, together with the adjacent nitrogen atom, a pyrrolidinyl or piperidyl radical; and one of R4 and R5 stands for hydrogen, and the other stands for hydrogen, a halogen atom or a (1-3C)alkyl or (1-3C)alkoxy radical; and acid-addition salts thereof. Processes for the manufacture of said compounds. Pharmaceutical compositions comprising one of said compounds and a pharmaceutical diluent or carrier. The compounds are 5-hydroxytryptamine antagonists.
Inventors
- 👤 Thomas P. Blackburn
- 👤 Barry Cox
- 👤 Allen J. Guildford
- 👤 David J. Le Count
- 👤 Robert J. Pearce
- 👤 Craig W. Thornber
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 19:19
CPC Classifications
C; C07; C07D; C07D211/00; C07D211/04; C07D211/06; C07D211/36; C07D211/40; C07D211/42; A; A61; A61P; A61P25/00; A61P25/08; A61P43/00; C07C; C07C233/00; C07C233/01; C07C233/02; C07C233/11; C07D215/00; C07D215/02; C07D215/16; C07D215/18; C07D215/36; C07D277/00; C07D277/02; C07D277/20; C07D277/22; C07D277/28; C07D333/00; C07D333/02; C07D333/04; C07D333/06; C07D333/24; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0803; C07F7/081; C07F7/0812
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
247 words
A quinoline derivative of the formula: ##STR36## wherein: A is a member selected from the group consisting of the radical --(CH 2 ) 2 --, the radical --(CH 2 ) 2 -- which is substituted by not more than two (1-2C)alkyl radicals, and the radical --(CH 2 ) 2 -- which is substituted by an alkylene radical so as to form, together with the residue of the --(CH 2 ) 2 -- radical, a cycloalkylene radical of not more than 6 carbon atoms; R 1 is a member selected from the group consisting of n-, iso- and s-(3-4C)alkyl, cyclopropyl and phenyl; and phenyl which bears not more than two substituents selected from the group consisting of halogen, hydroxy, (1-4C)alkyl, (1-4C)alkoxy, (1-4C)alkylthio, (1-2C)perfluoroalkyl, cyano, carboxy, (1-2C)alkoxy-carbonyl, carbamoyl, N-[(1-3C)alkyl]carbamoyl and N,N-di-[(1-3C)alkyl]carbamoyl; and furyl, thienyl, pyridyl, thiazolyl or oxazolyl, any of which may optionally be substituted by (1-2C)alkyl; R 2 is a member selected from the group consisting of hydrogen, methyl and ethyl, and dimethylene, trimethylene or tetramethylene which is linked to one or other of the carbon atoms forming the two-carbon-atom-backbone of radical A so as to form, together with the adjacent nitrogen atom, a pyrrolidinyl or piperidyl radical; R 3 is a member selected from the group consisting of hydrogen, methyl and ethyl; and one or R 4 and R 5 stands for hydrogen, and the other is a member selected from the group consisting of hydrogen, halogen atoms, (1-3C)alkyl and (1-3C)alkoxy; or a pharmaceutically-acceptable acid-addition salt thereof.
Claim 2
Dependent Claim
247 words
A quinoline derivative of the formula: ##STR36## wherein: A is a member selected from the group consisting of the radical --(CH 2 ) 2 --, the radical --(CH 2 ) 2 -- which is substituted by not more than two (1-2C)alkyl radicals, and the radical --(CH 2 ) 2 -- which is substituted by an alkylene radical so as to form, together with the residue of the --(CH 2 ) 2 -- radical, a cycloalkylene radical of not more than 6 carbon atoms; R 1 is a member selected from the group consisting of n-, iso- and s-(3-4C)alkyl, cyclopropyl and phenyl; and phenyl which bears not more than two substituents selected from the group consisting of halogen, hydroxy, (1-4C)alkyl, (1-4C)alkoxy, (1-4C)alkylthio, (1-2C)perfluoroalkyl, cyano, carboxy, (1-2C)alkoxy-carbonyl, carbamoyl, N-[(1-3C)alkyl]carbamoyl and N,N-di-[(1-3C)alkyl]carbamoyl; and furyl, thienyl, pyridyl, thiazolyl or oxazolyl, any of which may optionally be substituted by (1-2C)alkyl; R 2 is a member selected from the group consisting of hydrogen, methyl and ethyl, and dimethylene, trimethylene or tetramethylene which is linked to one or other of the carbon atoms forming the two-carbon-atom-backbone of radical A so as to form, together with the adjacent nitrogen atom, a pyrrolidinyl or piperidyl radical; R 3 is a member selected from the group consisting of hydrogen, methyl and ethyl; and one or R 4 and R 5 stands for hydrogen, and the other is a member selected from the group consisting of hydrogen, halogen atoms, (1-3C)alkyl and (1-3C)alkoxy; or a pharmaceutically-acceptable acid-addition salt thereof.
Claim 3
Dependent Claim
27 words
A compound as claimed in claim 1 wherein A is a member selected from the group consisting of 1,2-ethylene, 1,2-propylene, 2,3-propylene, 1,1-dimethyl-1,2-ethylene, 2,2-dimethyl-1,2-ethylene, cyclopropylene, 1,2-cis-cyclohexylene and 1,2-trans-cyclohexylene.
Claim 4
Dependent Claim
69 words
A compound as claimed in claim 1 wherein R 1 is a member selected from the group consisting of n-propyl, isopropyl, n-butyl, s-butyl, cyclopropyl and phenyl; and phenyl which is substituted by not more than two substituents selected from fluorine, chlorine and bromine atoms and hydroxy, (1-2C)alkyl, (1-4C)-alkoxy, (1-2C)alkylthio, trifluoromethyl, cyano carboxy, (1-2C)alkoxy-carbonyl, carbamoyl, N-[(1-2C)alkyl]carbamoyl and N,N-di-[(1-2C)alkyl]carbamoyl; and furyl, thienyl, pyridyl, thiazolyl, oxazolyl, (1-2C)alkyl-furyl, (1-2C)alkyl-thienyl, (1-2C)alkyl-pyridyl, (1-2C)alkyl-thiazolyl and (1-2C)alkyl-oxazolyl.
Claim 5
Dependent Claim
29 words
A compound as claimed in claim 1 which is a member selected from the group consisting of 2-(2-dimethylaminoethylthio)-3-isopropylquinoline, 2-(2-dimethylaminoethylthio)-3-p-fluorophenylquinoline, 2-(2-dimethylaminoethylthio)-3-o-methoxyphenylquinoline, 2-(2-dimethylaminoethylthio)-3-p-tolylquinoline, 2-(2-dimethylamino-2-methylpropylthio)-3-phenylquinoline and 2-(2-dimethylaminopropylthio)-3-phenylquinoline, and pharmaceutically-acceptable acid-addition salts thereof.
Claim 6
Dependent Claim
23 words
A compound as claimed in claim 1 which is a member selected from the group consisting of 2-(2-dimethylaminoethylthio)-3-phenylquinoline and pharmaceutically-acceptable acid-addition salts thereof.
Claim 7
Dependent Claim
57 words
A pharmaceutical composition for use as a 5-hydroxytryptamine antagonist comprising an effective amount of a quinoline derivative of the formula I, wherein A, R 1 , R 2 , R 3 , R 4 and R 5 have the meanings stated in claim 1, or a pharmaceutically-acceptable acid-addition salt thereof, and an inert pharmaceutically-acceptable diluent or carrier.
Claim 8
Dependent Claim
27 words
The method of inhibiting the activity of 5-hydroxytryptamine in warm-blooded animals which comprises administering to such animals an effective amount of a compound according to claim 1.
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) | 1987-03-06 | 1987-09-05 | 1988-03-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-03-06 | 1991-09-05 | 1992-03-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-03-06 | 1995-09-05 | 1996-03-06 | $7700.00 | Window Closed / Lapsed |