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US5041453A Expired / Lapsed US ⏱️ 0.0 years remaining

Quinolinyl-benzoheterobicyclic derivatives as antagonists of leukotriene D4

Assignee: Aventis Pharmaceuticals Inc
•
Filing: 1990-05-30
•
Granted: 1991-08-20
•
Expires: 2010-05-30
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Abstract

Abstract This invention relates to certain quinolinyl-benzoheterobicyclic compounds and their use as valuable pharmaceutical agents, particularly as lipoxygenase inhibitors and/or leukotriene antagonists and/or as mediator release inhibitors useful as anti-inflammatory and anti-allergic agents.

Inventors

  • 👤 Fu-chih Huang
  • 👤 Keith S. Learn
  • 👤 Ashvin V. Gavai

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 05:01
CPC Classifications
C; C07; C07D; C07D409/00; C07D409/02; C07D409/12; A; A61; A61P; A61P29/00; A61P37/00; A61P37/08; C07D409/14; C07D413/00; C07D413/02; C07D413/12; C07D413/14

Claims Analysis

Total Claims: 30
Claim 1
Independent Claim 350 words
A compound of the formula: ##STR29## where: A is O, S, ##STR30## or a carbon-carbon single bond; B is a carbon-carbon single bond, O, S, SO, SO 2 , NR 1 , ##STR31## D is O, S, NR 1 , ##STR32## or a carbon-carbon single bond; E is a carbon-carbon single bond or ##STR33## a is 0-1; b is 0-1; c is 0-3; d is 0-3; e is 0-3; f is 0-3; n is 0-2; X is NR 2 , O or S; Y is CR 2 R 3 or NR 2 when Z is CR 2 R 3 ; Z is CR 2 R 3 NR 2 , O or S; R' is independently hydrogen, alkyl, hydroxy, alkoxy, carboxy, carbalkoxy, halo, nitro, haloalkyl, cyano or acyl; R" is independently hydrogen, hydroxy, alkoxy, halo, haloalkyl, or --(CH 2 ) x --F--(CH 2 ) y --G; R 1 is independently hydrogen, alkyl or aralkyl; R 2 is a bond, hydrogen or alkyl; R 3 is hydrogen or together with a vicinal R 3 group a double bond; R is independently hydrogen or --(CH 2 ) x --F--(CH 2 ) y --G provided F and A or B are not geminal oxygen atoms; x is 0-3; y is 0-3; F is a carbon-carbon single bond, O, S or NR 1 ; G is hydrogen, alkyl, alkenyl, cycloalkyl, aryl, aralkyl, hydroxy, alkoxy, aralkoxy, amino, mono- and di-alkylamino, aralkylamino, acylamino, --CONR 1 R 1 , --COOR, CN, tetrazolyl, ##STR34## where R 4 is hydrogen, alkyl haloalkyl, phenyl or benzyl; vicinal R groups together may be (CH 2 ) y --where y is 1-4, thus forming a 3-6 membered ring; geminal R 1 and R 1 groups may together form a spiro substituent, --(CH 2 ) 2 --, where z is 2-5; geminal R 1 or R 1 and R groups may together form an alkylidenyl substitutent, ##STR35## Q is --COOR 1 ,--CN, ##STR36## where R 4 is as described above, ##STR37## --OR 1 , tetrazolyl, substituted tetrazolyl where the substituent may be alkyl, carboxyalkyl or carbalkoxyalkyl or ##STR38## or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim 350 words
A compound of the formula: ##STR29## where: A is O, S, ##STR30## or a carbon-carbon single bond; B is a carbon-carbon single bond, O, S, SO, SO 2 , NR 1 , ##STR31## D is O, S, NR 1 , ##STR32## or a carbon-carbon single bond; E is a carbon-carbon single bond or ##STR33## a is 0-1; b is 0-1; c is 0-3; d is 0-3; e is 0-3; f is 0-3; n is 0-2; X is NR 2 , O or S; Y is CR 2 R 3 or NR 2 when Z is CR 2 R 3 ; Z is CR 2 R 3 NR 2 , O or S; R' is independently hydrogen, alkyl, hydroxy, alkoxy, carboxy, carbalkoxy, halo, nitro, haloalkyl, cyano or acyl; R" is independently hydrogen, hydroxy, alkoxy, halo, haloalkyl, or --(CH 2 ) x --F--(CH 2 ) y --G; R 1 is independently hydrogen, alkyl or aralkyl; R 2 is a bond, hydrogen or alkyl; R 3 is hydrogen or together with a vicinal R 3 group a double bond; R is independently hydrogen or --(CH 2 ) x --F--(CH 2 ) y --G provided F and A or B are not geminal oxygen atoms; x is 0-3; y is 0-3; F is a carbon-carbon single bond, O, S or NR 1 ; G is hydrogen, alkyl, alkenyl, cycloalkyl, aryl, aralkyl, hydroxy, alkoxy, aralkoxy, amino, mono- and di-alkylamino, aralkylamino, acylamino, --CONR 1 R 1 , --COOR, CN, tetrazolyl, ##STR34## where R 4 is hydrogen, alkyl haloalkyl, phenyl or benzyl; vicinal R groups together may be (CH 2 ) y --where y is 1-4, thus forming a 3-6 membered ring; geminal R 1 and R 1 groups may together form a spiro substituent, --(CH 2 ) 2 --, where z is 2-5; geminal R 1 or R 1 and R groups may together form an alkylidenyl substitutent, ##STR35## Q is --COOR 1 ,--CN, ##STR36## where R 4 is as described above, ##STR37## --OR 1 , tetrazolyl, substituted tetrazolyl where the substituent may be alkyl, carboxyalkyl or carbalkoxyalkyl or ##STR38## or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim 65 words
A compound of claim 1 where: one of R is --(CH 2 ) x --F--(CH 2 ) y --G, --S--(CH 2 ) x --G or --NR 1 -(CH 2 ) x --G; and/or one of R" is --CH 2 R, R or --CH 2 -O-(CH 2 ) x --G and G is --CONR 1 R 1 , --COOR 1 , --CN, tetrazolyl, ##STR39## or acylsulfonamido.
Claim 4
Dependent Claim 37 words
A compound of claim 2 where: B is O, S, ##STR40## or a carbon-carbon single bond; Q is --COOR 1 , --CON(R 1 ) 2 , tetrazolyl or ##STR41## and R and R" are as described above.
Claim 5
Dependent Claim 8 words
A compound of claim 1 which is 5-(6-(3-(2-quinolinyl-methyloxy)phenoxymethyl)benzoxazol-2-yl)tetrazole.
Claim 6
Dependent Claim 8 words
A compound of claim 1 which is 5-(6-(4-(2-quinolinyl-methyloxy)phenoxymethyl)benzoxazol-2-yl)tetrazole.
Claim 7
Dependent Claim 8 words
A compound of claim 1 which is 2-ethoxyethyl-6-[3-(2quinolinylmethyloxy)phenoxymethyl]benzoxazole-2carboxylate.
Claim 8
Dependent Claim 9 words
A compound of claim 1 which is trans-(E)-5-(6-(2-(3-quinolin-2-ylmethyloxy)phenyl)ethenyl)benzoxazol -2-yl)tetrazole.
Claim 9
Dependent Claim 9 words
A compound of claim 1 which is 5-(6-(2-(3-(quinolin-2-ylmethyloxy)phenyl)ethyl)benzoxazol-2-yl) tetrazole.
Claim 10
Dependent Claim 8 words
A compound of claim 1 which is 5-(6-(3-(quinolin-2-ylmethyloxy)benzyloxy)benzoxazol-2-yl)tetrazole.
Claim 11
Dependent Claim 8 words
A compound of claim 1 which is n-propyl-5-(3-(quinolin-2-ylmethyloxy)benzyloxy)benzoxazole-2carboxylate.
Claim 12
Dependent Claim 9 words
A compound of claim 1 which is 5-(3-(quinolin-2-ylmethyloxy)benzyloxy)benzoxazole-2-carboxylic acid.
Claim 13
Dependent Claim 8 words
A compound of claim 1 which is ethyl-6-(3-(quinolin-2-ylmethyloxy)benzyloxy)benzoxazole-2-carboxylate.
Claim 14
Dependent Claim 8 words
A compound of claim 1 which is 5-(7-(quinolin-2-ylmethyloxy)phenoxymethyl)benzoxazol-2-yl)tetrazole.
Claim 15
Dependent Claim 9 words
A compound of claim 1 which is 6-(4-(quinolin-2-ylmethyloxy)phenoxymethyl)benzoxazole-2-carboxylic acid.
Claim 16
Dependent Claim 9 words
A compound of claim 1 which is (E)-5-(6-[3-(7-chloro-2-quinolinylethenyl)phenoxymethyl)benzoxazol -2yl)tetrazole.
Claim 17
Dependent Claim 8 words
A compound of claim 1 which is 5-(6-[4-(7-chloro-2quinolinylethenyl)phenoxymethyl]benzoxazol-2-yl)tetrazole.
Claim 18
Dependent Claim 8 words
A compound of claim 1 which is 5-(5-[3-(7-chloro-2-quinolinylethenyl)phenoxymethyl]benzoxazol-2-yl)tetrazole.
Claim 19
Dependent Claim 10 words
A compound of claim 1 which is 5-[3-(7-chloro-2quinolinylethenyl)phenoxymethyl]-3-methylbenzo(b) -thiophene-2-carboxylic acid.
Claim 20
Dependent Claim 9 words
A compound of claim 1 which is 5-[4-(7-chloro-2quinolinylethenyl)phenoxymethyl]benzo(b)thiophene-2carboxylic acid.
Claim 21
Dependent Claim 9 words
A compound of claim 1 which is 3-methyl-5-[3-(2quinolinylmethyloxy)benzyloxy]benzo(b)thiophene-2carboxylic acid.
Claim 22
Dependent Claim 9 words
A compound of claim 1 which is 5-[3-(2-quinolinylmethyloxy)benzyloxy]benzo(b)thiophene-2-carboxylic acid.
Claim 23
Dependent Claim 9 words
A compound of claim 1 which is 3-methyl-5-[4-(2quinolinylmethyloxy)benzyloxy]benzo(b)thiophene-2carboxylic acid.
Claim 24
Dependent Claim 9 words
A compound of claim 1 which is 5-[4-(2-quinolinylmethyloxy)benzyloxy]benzo(b)thiophene-2-carboxylic acid.
Claim 25
Dependent Claim 9 words
A compound of claim 1 which is 5-(5-[3-(2-quinolinylmethyloxy)benzyloxy]-3-methylbenzo(b)thiophen -2-yl)tetrazole.
Claim 26
Dependent Claim 9 words
A compound of claim 1 which is 5-(5-[4-(2-quinolinylmethyloxy)benzyloxy]-3-methylbenzo(b)thiophen -2-yl)tetrazole.
Claim 27
Dependent Claim 9 words
A compound of claim 1 which is 5-(5-[4-(2-quinolinylmethyloxy)benzyloxy]benzo(b)thiophen-2-yl) tetrazole.
Claim 28
Dependent Claim 8 words
A compound of claim 1 which is N-1H-(5-tetrazolyl)-5[3-(2-quinolinylmethyloxy)benzyloxy]-3-methylbenzo(b)-thiophene-2-carboxamide.
Claim 29
Dependent Claim 28 words
A method for the treatment of hypersensitive ailments in humans and mammals comprising administering thereto an effective amount of a compound of the formula according to claim 1.
Claim 30
Dependent Claim 20 words
A pharmaceutical composition wherein the active ingredient is a compound according to claim 1 in admixture with a pharmaceutical carrier.

References Cited (Backward Citations)

US4186201A Cited
US4851409A Cited
US4920131A Cited
US4946855A Cited
EP0387610A2 Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1994-08-19 1995-02-18 1995-08-20 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1998-08-19 1999-02-18 1999-08-20 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2002-08-19 2003-02-18 2003-08-20 $7700.00 Window Closed / Lapsed

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