EP0190722A2
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EP
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Dihydro and tetrahydroquinoline derivatives
Assignee: USV Pharmaceutical Corp
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Filing: 1986-02-04
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Granted: —
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Expires: 2006-02-04
Abstract
Abstract This invention relates to novel lipoxygenase inhibitors possessing anti-inflammatory and anti-allergic activities. The present new compounds are di-and tetra-hydroquinoline or di- and tetra-hydronapthalene derivatives, more particularly, 1,2-, 1,4-, 5,6-, or 7,8-dihydro; 1,2,3,4,-tetrahydro-; 5,8-dihydro-; or 5,6,7,8-tetrahydroquinoline or napthalene derivatives of a compound of the formula: and oxides, quaternary ammonium salts and acid salts thereof; wherein A is CH or N; Z is an alkylene chain containing up to 10 carbon atoms in the principal chain and a total of up to 12 carbon atoms and the said alkylene chain may be attached to the phenyl group through an oxygen atom; R is the substituent OR 6 attached to one of the carbon atoms of Z in which R 6 is H, lower alkyl or phenyl; X is -0(CHR 5 ) m -, alkylene of up to 2 carbon atoms in the principal chain and up to a total of 4 carbon atoms or - -C (CHR 5 ) m -, wherein R 5 is H or CH 3 ; OH R 1 , R 2 , R 3 , and R 4 , are each H or OH; n' = 1 or 2; and m = 1 or 2.
Inventors
- 👤 Edward S. Neiss
- 👤 Rohit M. Desai
- 👤 Raymond D. Youssefyeh
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-07 14:07
CPC Classifications
C; C07; C07D; C07D215/00; C07D215/02; C07D215/16; C07D215/20; C07D215/22; C07D215/233; A; A61; A61P; A61P29/00; A61P37/00; A61P37/08; A61P43/00; C07C; C07C17/00; C07C17/093; C07C309/00; C07C33/00; C07C33/34; C07C43/00; C07C43/02; C07C43/20; C07C43/23; C07D215/12; C07D215/14; C07D215/58; C07D215/60
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
160 words
A 1,2-dihydro; 1,2,3,4-cetrahydro; 5,8-dihydro; or 5,6,7, 8 -tetrahydro derivative of a compound of the formula: and acid salts thereof; wherein A is N or CH; Z is an alkylene chain containing up to 10 carbon atoms in the principal chain and a total of up to 12 carbon atoms and the said alkylene chain may be attached to the phenyl group through an oxygen atom; R is the substituent OR 6 attached to one of the carbon atoms of Z in which R 6 is H, lower alkyl. or phenyl; X is -O(CHR 5 ) m -, alkylene of up to 2 carbon atoms in the principal chain and up to a total of 4 carbon atoms or -C(CHR 5 ) m - wherein R 5 is H or CH 3 ; OH R 1 , R 2 , R 3 and R 4 are each II or OH; n' = 1 or 2; and m = 1 or 2.
Claim 2
Dependent Claim
160 words
A 1,2-dihydro; 1,2,3,4-cetrahydro; 5,8-dihydro; or 5,6,7, 8 -tetrahydro derivative of a compound of the formula: and acid salts thereof; wherein A is N or CH; Z is an alkylene chain containing up to 10 carbon atoms in the principal chain and a total of up to 12 carbon atoms and the said alkylene chain may be attached to the phenyl group through an oxygen atom; R is the substituent OR 6 attached to one of the carbon atoms of Z in which R 6 is H, lower alkyl. or phenyl; X is -O(CHR 5 ) m -, alkylene of up to 2 carbon atoms in the principal chain and up to a total of 4 carbon atoms or -C(CHR 5 ) m - wherein R 5 is H or CH 3 ; OH R 1 , R 2 , R 3 and R 4 are each II or OH; n' = 1 or 2; and m = 1 or 2.
Claim 3
Dependent Claim
105 words
A 1,2-dihydro; 1,2',3,4-tetrahydro; 5, 8-dihydro or 5,5,7,8-tetrahydro derivative of a compound of the formula: and salts thereof; wherein A is CH or N; Z is an alkylene chain containing up to 10 carbon atoms in the principal chain and a total of up to 12 carbon atoms and the said alkylene chain may be attached to the phenyl group through an oxygen atom; R is the substituent OR 6 attached to one of the carbon atoms of Z in which R 6 is H, lower alkyl or phenyl; and R 1 , R 2 , R 3 and R 4 are each H or OH.
Claim 4
Dependent Claim
105 words
A 1,2-dihydro; 1,2',3,4-tetrahydro; 5, 8-dihydro or 5,5,7,8-tetrahydro derivative of a compound of the formula: and salts thereof; wherein A is CH or N; Z is an alkylene chain containing up to 10 carbon atoms in the principal chain and a total of up to 12 carbon atoms and the said alkylene chain may be attached to the phenyl group through an oxygen atom; R is the substituent OR 6 attached to one of the carbon atoms of Z in which R 6 is H, lower alkyl or phenyl; and R 1 , R 2 , R 3 and R 4 are each H or OH.
Claim 5
Dependent Claim
94 words
A 1,2-dihydro; 1,2,3,4-tetrahydro; 5,8-dihydro or 5,6,7,8-tetrahydro derivative of a compound of the formula: and salts thereof; wherein A is N or CH ; Z is an alkylene chain containing up to 10 carbon atoms in the principal chain and a total of up to 12 carbon atoms and the said alkylene chain may be attached to the phenyl group through an oxygen atom and the OH substituent is located on any one of the carbon atoms of Z; and R1 , A 2 , R 3 and R 4 are each H or OH.
Claim 6
Dependent Claim
94 words
A 1,2-dihydro; 1,2,3,4-tetrahydro; 5,8-dihydro or 5,6,7,8-tetrahydro derivative of a compound of the formula: and salts thereof; wherein A is N or CH ; Z is an alkylene chain containing up to 10 carbon atoms in the principal chain and a total of up to 12 carbon atoms and the said alkylene chain may be attached to the phenyl group through an oxygen atom and the OH substituent is located on any one of the carbon atoms of Z; and R1 , A 2 , R 3 and R 4 are each H or OH.
Claim 7
Dependent Claim
17 words
The compound according to Claim 3 wherein the OH group on Z is a secondary alcohol group.
Claim 8
Dependent Claim
24 words
The compound according to Claim 3 wherein the OH group on Z is attached to the carbon atom attached directly to the phenyl group.
Claim 9
Dependent Claim
32 words
The compound according to Claim 3 which is 1,2-dihydro-2-(3-(1-hydroxyhexyl)phenoxy)-methyl)quinoline; 2-(3-(1-hydroxyhexyl)phenoxy)methyl-1,2,2,4-tetrahydroquinoline-3,4-diol; 5,8-dihydro-2-(3-(1-hydroxy-2-metnylhexyl)-phenoxy)methylquinoline; 1,2,3.4-tetrahydro-2-(3-(1-hydroxyhexyl)phenoxy)methylquinoline; 2-(3-(1-hydroxyhexyl)phenoxy)methyl-5,6,7,o-tetrahxdro- quinoline-6,7-diol 2-(3-(1-hydroxyhexyl)phenoxy)methyl-5,6,7,8-tetra hydroquinoline; 2-(3-(1-hydroxy-2-methylhexyl)phenoxy)methyl-1,2,3,4-tetrahydroquinoline; 2-(3-(1-hydroxy-2,2-dimethylhexyl)phenoxy)methyl-5,8-dihydroquinoline; 2-(3-(1-hydroxy-2-methylhexyl)phenoxy)methyl-5,6,7,8-tetrahydroquinoline-6,7-diol; 2-(3-(1-hydroxy-2,2-dimethylhexyl)phenoxy)methyl-1,2-dihydroquinoline; 2-(3-(1-hydroxy-2,2-dimethylhexyl)phenoxy)methyl-1,2,3,4-tetrahydroquinoline-3,4-diol; 2-(3-(2-hydroxy-2-heptyl)phenoxy)methyl-5,8-dihydroquinoline; 2-(3-(l-hydroxy-2-methylhexyl)phenoxy)methyl-5,6,7,8-tetrahydroquinoline; 2-(3-(1-hydroxy-2,2-dimethylhexyl)phenoxy)methyl-5,6,7,8-tetrahydroquinoline-6,7-diol; 2-(3-(2-hydroxy-2-heptyl)phenoxy)methyl-1,2,3 1 4-tetra- hydroquinoline; 2-(3-(1-hydroxy-2-phenoxyethyl)phenoxy)methyl-1,2,3,4-tetrahydroquinoline-3,4-diol; 2-(3-(1-hydroxy-2-methylhexyl)phenoxy)methyl-1,2-dihydroquinoline; or 2-(3-(1-hydroxy-2-phenoxyethyl)phenoxy)methyl-5,6,7,8-tetrahydroquinoline.
Claim 10
Dependent Claim
16 words
A therapeutic composition comprising a derivative of any of Claims 1-6 and a pharmaceutical carrier therefor.
References Cited (Backward Citations)
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