Patent EP0271287A2 successfully refreshed from Google Patents.
EP0271287A2
Expired / Lapsed
EP
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Quinoline dioic acids and amides
Assignee: Merck Frosst Canada and Co
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Filing: 1987-12-03
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Granted: —
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Expires: 2007-12-03
Abstract
Abstract Compounds having the formula are antagonists of leukotrienes and inhibitors of their biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents.
Inventors
- 👤 Robert N. Young
- 👤 Robert Zamboni
- 👤 Haydn W. R. Williams
- 👤 Michel L. Belley
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-09 03:59
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/10; A; A61; A61P; A61P1/00; A61P1/16; A61P11/00; A61P13/00; A61P13/02; A61P15/00; A61P29/00; A61P37/00; A61P37/08; A61P39/00; A61P39/02; A61P43/00; C07D215/00; C07D215/02; C07D215/16; C07D215/18; C07D401/12; C07D401/14
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
569 words
A compound of the formula: wherein: R 1 is H, halogen, C 1 -C 8 alkyl, C 2 -Ca alkenyl, C 2 -C 8 alkynyl, -CF 3 , -OR 2 , -SR 2 , -S(O)R 2 , -S(O) 2 R 2 , -NR 2 R 2 , -CHO, -COOR 2 , -(C=O)R2, -C(OH)R2R 2 , -CN, -N0 2 , substituted or unsubstituted phenyl, substituted or unsubstituted benzyl, or substituted or unsubstituted phenethyl; R 2 is H, C 1 -Ca alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, -CF 3 , substituted or unsubstituted phenyl, substituted or unsubstituted benzyl, or substituted or unsubstituted phenethyl; R 3 is H, halogen, -N0 2 , -CN, -OR 2 , -SR 2 , NR 2 R 2 , or C 1 -C 8 alkyl; CR 2 R 3 may be the radical of a naturally occurring amino acid; R 4 is H, halogen, -N0 2 , -CN, -OR 2 , -SR 2 , NR 2 R 2 , C 1 -C 8 alkyl, or -(C=O)R 2 ; R5 is R 6 is H or C 1 -C 4 alkyl; R 7 is A) a monocyclic or bicyclic heterocyclic radical containing from 3 to 12 nuclear carbon atoms and 1 or 2 nuclear heteroatoms selected from N, S or 0 and with each ring in the heterocyclic radical being formed of 5 or 6 atoms, or B) the radical W-R 8; R 8 contains up to 21 carbon atoms and is (1) a hydrocarbon radical or (2) an acyl radical of an organic acyclic or monocyclic carboxylic acid containing not more than 1 heteroatom in the ring; R 9 is-OR 10 , -SR 10 , or NR 10 R 10 ; R 10 is H, Ci-C 6 alkyl, -(C=O)R 11 , unsubstituted phenyl, unsubstituted benzyl, or two R 10 groups joined to the same N may form a ring of 5 or 6 members containing up to two heteratoms chosen from O,S or N; R 11 is H, c 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, -CF 3 , or unsubstituted phenyl, benzyl, or phenethyl; R 12 is R 2 or halogen; m and m'are independently 0-8; n and n' are independently 0 or 1; p and p' are independently 0-8; m+n+p is 1-10; m'+n'+p' is 0-10; s is 0-3; Q 1 and Q 2 are independently -COOR 2 , tetrazole, -COOR 5 , -CONHS(O) 2 R 11 , -CN, -CONR 10 R 10 , -CHO, -CH 2 0H, -COCH 2 0H, -NHS(O) 2 R 11 ; or if Q 1 or Q 2 is COOH and R 3 is -OH, -SH, or -NHR 2 then Q 1 or Q 2 and R 3 and the carbons through which they are attached may form a heterocyclic ring with loss of water; W is O, S, or NH; X 1 is 0, S, -S(O)-, -S(O) 2 -, -NR 2 , or -CR 2 R 2 -; X 2 is CR 2 R 2 , O, S, S(O), or S(O)2; Y is -CR 2 =CR 2 -, -C=C-, -CR 2 R 2 -X 1 -, -X 1 -CR 2 R 2 -, -CR 2 R 2 -X 1 -CR 2 R 2 -, C=O, O, S, or - NR 2 ; Z 1 and Z 2 are independently -CONR 2- ; and the pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim
569 words
A compound of the formula: wherein: R 1 is H, halogen, C 1 -C 8 alkyl, C 2 -Ca alkenyl, C 2 -C 8 alkynyl, -CF 3 , -OR 2 , -SR 2 , -S(O)R 2 , -S(O) 2 R 2 , -NR 2 R 2 , -CHO, -COOR 2 , -(C=O)R2, -C(OH)R2R 2 , -CN, -N0 2 , substituted or unsubstituted phenyl, substituted or unsubstituted benzyl, or substituted or unsubstituted phenethyl; R 2 is H, C 1 -Ca alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, -CF 3 , substituted or unsubstituted phenyl, substituted or unsubstituted benzyl, or substituted or unsubstituted phenethyl; R 3 is H, halogen, -N0 2 , -CN, -OR 2 , -SR 2 , NR 2 R 2 , or C 1 -C 8 alkyl; CR 2 R 3 may be the radical of a naturally occurring amino acid; R 4 is H, halogen, -N0 2 , -CN, -OR 2 , -SR 2 , NR 2 R 2 , C 1 -C 8 alkyl, or -(C=O)R 2 ; R5 is R 6 is H or C 1 -C 4 alkyl; R 7 is A) a monocyclic or bicyclic heterocyclic radical containing from 3 to 12 nuclear carbon atoms and 1 or 2 nuclear heteroatoms selected from N, S or 0 and with each ring in the heterocyclic radical being formed of 5 or 6 atoms, or B) the radical W-R 8; R 8 contains up to 21 carbon atoms and is (1) a hydrocarbon radical or (2) an acyl radical of an organic acyclic or monocyclic carboxylic acid containing not more than 1 heteroatom in the ring; R 9 is-OR 10 , -SR 10 , or NR 10 R 10 ; R 10 is H, Ci-C 6 alkyl, -(C=O)R 11 , unsubstituted phenyl, unsubstituted benzyl, or two R 10 groups joined to the same N may form a ring of 5 or 6 members containing up to two heteratoms chosen from O,S or N; R 11 is H, c 1 -C 8 alkyl, C 2 -C 8 alkenyl, C 2 -C 8 alkynyl, -CF 3 , or unsubstituted phenyl, benzyl, or phenethyl; R 12 is R 2 or halogen; m and m'are independently 0-8; n and n' are independently 0 or 1; p and p' are independently 0-8; m+n+p is 1-10; m'+n'+p' is 0-10; s is 0-3; Q 1 and Q 2 are independently -COOR 2 , tetrazole, -COOR 5 , -CONHS(O) 2 R 11 , -CN, -CONR 10 R 10 , -CHO, -CH 2 0H, -COCH 2 0H, -NHS(O) 2 R 11 ; or if Q 1 or Q 2 is COOH and R 3 is -OH, -SH, or -NHR 2 then Q 1 or Q 2 and R 3 and the carbons through which they are attached may form a heterocyclic ring with loss of water; W is O, S, or NH; X 1 is 0, S, -S(O)-, -S(O) 2 -, -NR 2 , or -CR 2 R 2 -; X 2 is CR 2 R 2 , O, S, S(O), or S(O)2; Y is -CR 2 =CR 2 -, -C=C-, -CR 2 R 2 -X 1 -, -X 1 -CR 2 R 2 -, -CR 2 R 2 -X 1 -CR 2 R 2 -, C=O, O, S, or - NR 2 ; Z 1 and Z 2 are independently -CONR 2- ; and the pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim
36 words
A compound of Claim 1 of the Formula la: wherein: Y is -CR 2 =CR 2 -, -C=C-, , or ; the other substituents are as defined for Formula I; and the pharmaceutically acceptable salts thereof.
Claim 4
Dependent Claim
59 words
A compound of Claim 1 of the Formula Ib: wherein: R 1 is H, halogen, C 1 -C 3 alkyl,-CF 3 , or SCF 3 ; R 2 is H, C 1 -C 3 alkyl, C 2 -C 3 alkenyl, or -CF 3 ; the other substituents are as defined for Formula I; and the pharmaceutically acceptable salts thereof.
Claim 5
Dependent Claim
57 words
A compound of Claim 1 of the Formula Ic: wherein: R 1 is H, halogen, C 1 -C 3 alkyl, -CF 3 , or SCF 3 ; R 2 is H, C 1 -C 3 alkyl, C 2 -C 3 alkenyl, or-CF3; the other substituents are as defined for Formula I; and the pharmaceutically acceptable salts thereof.
Claim 6
Dependent Claim
64 words
A compound of Claim 1 of the Formula Id: wherein: R 1 is H, halogen, C 1 -C 3 alkyl, CF 3 or SCF 3 ; R 2 is H, C 1 -C 3 alkyl, C 2 -C 3 alkenyl, or CF 3 ; Y is - or ; the other substituents are as defined for Formula I; and the pharmaceutically acceptable salts thereof.
Claim 7
Dependent Claim
10 words
A compound of Claim 1 of Formula le which is:
Claim 8
Dependent Claim
29 words
A pharmaceutical composition useful in antagonizing leukotriene action in mammals comprising an amount of a compound of Claim 1 effective as a leukotriene antagonist and a pharmaceutically acceptable carrier.
Claim 9
Dependent Claim
47 words
The pharmaceutical composition of Claim 7 additionally comprising an effective amount of a second active ingredient selected from the group consisting of non-steroidal anti-inflammatory drugs; peripheral analgesic agents; cyclooxygenase inhibitors; leukotriene antagonists; leukotriene inhibitors; H 2 -receptor antagonists; antihistaminic agents; prostaglandin antagonists; thromboxane antagonists; and serotonin antagonists.
Claim 10
Dependent Claim
32 words
The use of a compound of Claim 1 for the preparation of a medicament useful for preventing the synthesis, the action, or the release of SRS-A or leukotriene D 4 in mammals.
Claim 11
Dependent Claim
24 words
The use of a compound of Claim 1 for the preparation of a medicament useful for treating inflammatory diseases of the eye in mammals.
References Cited (Backward Citations)
No citation records indexed.
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