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US4920131A Expired / Lapsed US ⏱️ 0.0 years remaining

Quinoline derivatives and use thereof as antagonists of leukotriene D4

Assignee: Aventis Pharmaceuticals Inc
•
Filing: 1988-06-21
•
Granted: 1990-04-24
•
Expires: 2008-06-21
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Abstract

Abstract This invention relates to quinolinyl compounds of the general formula: ##STR1## and the use of these compounds as pharmacological agents which are lipoxygenase inhibitors and/or leukotriene antagonists possessing anti-inflammatory and anti-allergic properties and their pharmaceutical compositions and processes for this preparation.

Inventors

  • 👤 Fu-Chi Huang
  • 👤 Robert A. Galemmo, Jr.
  • 👤 Henry F. Campbell

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-03 08:41
CPC Classifications
C; C07; C07D; C07D401/00; C07D401/02; C07D401/12; C07D215/00; C07D215/02; C07D215/12; C07D215/14; C07D215/16; C07D215/18; C07D215/20

Claims Analysis

Total Claims: 20
Claim 1
Independent Claim 398 words
A compound of the formula ##STR25## where: A is O or S; B is a chemical bond, O, S, SO, SO 2 , NR 1 , ##STR26## D is O, S, NR 1 , ##STR27## or a chemical bond; E is a chemical bond or ##STR28## a is 0-2; b is 0-1; c is 0-4; d is 0-5; e is 0-4; f is 0-5; n is 0-2; R' is independently hydrogen, alkyl having 1 to 6 carbon atoms, hydroxy, alkoxy having 1 to 6 carbon atoms, carboxy, carbalkoxy wherein alkoxy has 1 to 6 carbon atoms, halo, nitro, trifluoromethyl, cyano, acetyl, propionyl or benzoyl; R" is independently hydrogen, hydroxy, alkoxy having 1 to 6 carbon atoms, halo, trifluoromethyl, --CH 2 R, --CH 2 --O--(CH 2 ) x --X or R; R 1 is independently hydrogen, alkyl having 1 to 6 carbon atoms, benzyl or phenethyl; R is --(CH 2 ) x --X, --O--(CH 2 ) x --X (when not geminal to A or B when A or B is O); --S--(CH 2 ) x --X or --NR 1 --(CH 2 ) x --X where x is 0-3; and X is hydrogen, alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, phenyl, benzyl, phenethyl, hydroxy, alkoxy having 1 to 6 carbon atoms, aralkoxy wherein aryl is phenyl and alkoxy has 1 to 6 carbon atoms, amino, mono- and di-alkylamino having 1 to 6 carbon atoms, benzylamino, phenethylamino, acetylamino, propionylamino, benzoylamino, --CONR 1 R 1 , --COOR, --CN, tetrazolyl, acetylsulfonamido, propionylsulfonamido or benzoylsulfonamido; 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 groups may together form a spiro substituent, --(CH 2 ) z --, where z is 2 to 5; geminal R 1 or R 1 and R groups may together form an alkylidenyl substituent, ##STR29## Z is --COOR 1 ; --CN; ##STR30## where R 3 is hydrogen, alkyl having 1 to 6 carbon atoms, trifluoromethyl, phenyl or benzyl; ##STR31## --OR 1 or tetrazolyl or substituted tetrazolyl where the substituent may be alkyl having 1 to 6 carbon atoms, carboxyalkyl wherein alkyl has 1 to 6 carbon atoms, or carbalkoxyalkyl wherein alkoxy has 1 to 6 carbon atoms and alkyl has 1 to 6 carbon atoms; and pharmaceutically acceptable salts thereof.
Claim 2
Dependent Claim 398 words
A compound of the formula ##STR25## where: A is O or S; B is a chemical bond, O, S, SO, SO 2 , NR 1 , ##STR26## D is O, S, NR 1 , ##STR27## or a chemical bond; E is a chemical bond or ##STR28## a is 0-2; b is 0-1; c is 0-4; d is 0-5; e is 0-4; f is 0-5; n is 0-2; R' is independently hydrogen, alkyl having 1 to 6 carbon atoms, hydroxy, alkoxy having 1 to 6 carbon atoms, carboxy, carbalkoxy wherein alkoxy has 1 to 6 carbon atoms, halo, nitro, trifluoromethyl, cyano, acetyl, propionyl or benzoyl; R" is independently hydrogen, hydroxy, alkoxy having 1 to 6 carbon atoms, halo, trifluoromethyl, --CH 2 R, --CH 2 --O--(CH 2 ) x --X or R; R 1 is independently hydrogen, alkyl having 1 to 6 carbon atoms, benzyl or phenethyl; R is --(CH 2 ) x --X, --O--(CH 2 ) x --X (when not geminal to A or B when A or B is O); --S--(CH 2 ) x --X or --NR 1 --(CH 2 ) x --X where x is 0-3; and X is hydrogen, alkyl having 1 to 6 carbon atoms, alkenyl having 2 to 6 carbon atoms, cycloalkyl having 3 to 6 carbon atoms, phenyl, benzyl, phenethyl, hydroxy, alkoxy having 1 to 6 carbon atoms, aralkoxy wherein aryl is phenyl and alkoxy has 1 to 6 carbon atoms, amino, mono- and di-alkylamino having 1 to 6 carbon atoms, benzylamino, phenethylamino, acetylamino, propionylamino, benzoylamino, --CONR 1 R 1 , --COOR, --CN, tetrazolyl, acetylsulfonamido, propionylsulfonamido or benzoylsulfonamido; 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 groups may together form a spiro substituent, --(CH 2 ) z --, where z is 2 to 5; geminal R 1 or R 1 and R groups may together form an alkylidenyl substituent, ##STR29## Z is --COOR 1 ; --CN; ##STR30## where R 3 is hydrogen, alkyl having 1 to 6 carbon atoms, trifluoromethyl, phenyl or benzyl; ##STR31## --OR 1 or tetrazolyl or substituted tetrazolyl where the substituent may be alkyl having 1 to 6 carbon atoms, carboxyalkyl wherein alkyl has 1 to 6 carbon atoms, or carbalkoxyalkyl wherein alkoxy has 1 to 6 carbon atoms and alkyl has 1 to 6 carbon atoms; and pharmaceutically acceptable salts thereof.
Claim 3
Dependent Claim 82 words
A compound of claim 1 of the formula ##STR32## where one of R is --(CH 2 ) x --X; --S--(CH 2 ) x --X; --O--(CH 2 ) x --X; (when not geminal to A or B when A or B is O); or --NR 1 --(CH 2 ) x --X; and/or one of R" is --CH 2 R; R or --CH 2 --O--(CH 2 ) x --X and X is --CONR 1 R 1 , --COOR 1 , --CN, tetrazolyl or acylsulfonamido.
Claim 4
Dependent Claim 25 words
A compound of claim 2 where B is O, S, ##STR33## or a chemical bond; Z is --COOR 1 --CON(R 1 ) 2 or tetrazolyl.
Claim 5
Dependent Claim 9 words
A compound of claim 3 of the formula ##STR34##
Claim 6
Dependent Claim 9 words
A compound of claim 3 of the formula ##STR35##
Claim 7
Dependent Claim 9 words
A compound of claim 3 of the formula ##STR36##
Claim 8
Dependent Claim 9 words
A compound of claim 3 of the formula ##STR37##
Claim 9
Dependent Claim 9 words
A compound of claim 3 of the formula ##STR38##
Claim 10
Dependent Claim 9 words
A compound of claim 3 of the formula ##STR39##
Claim 11
Dependent Claim 8 words
A compoundof claim 3 of the formula ##STR40##
Claim 12
Dependent Claim 9 words
A compound of claim 3 of the formula ##STR41##
Claim 13
Dependent Claim 9 words
A compound of claim 3 of the formula ##STR42##
Claim 14
Dependent Claim 9 words
A compound of claim 3 of the formula ##STR43##
Claim 15
Dependent Claim 10 words
A compound according to claim 1 which is 2-hydroxy-3-((2-carboxyethyl)thio-3-[(2-(4-((quinolin-2-yl)methyloxy)phenoxymethyl)phenyl]propionic acid.
Claim 16
Dependent Claim 10 words
A compound according to claim 12 which is 4-(2-(4-((quinolin-2-yl)metholoxy)phenoxymethyl)phenoxy)-4-carboxybutyric acid.
Claim 17
Dependent Claim 10 words
A compound according to claim 11 which is 3-(-1-[3-(3-(2-quinolinylmethyloxy)phenoxy)benzyl]-1-(N,N-dimethylcarbamylethylthio)thiomethyl)propionic acid.
Claim 18
Dependent Claim 10 words
A compound according to claim 1 which is 2-(3-(3-(quinolin-2-yl)methyloxy)phenoxymethyl)phenoxy)valeric acid.
Claim 19
Dependent Claim 33 words
A method for the treatment of hypersensitive ailments in a patient requiring such treatment which comprises administering to such patient an effective amount of a compound of the formula according to claim 1.
Claim 20
Dependent Claim 32 words
A pharmaceutical composition for the treatment of hypersensitive ailments in a patient requiring such treatment comprising an effective amount of a compound according to claim 1 in admixture with a pharmaceutical carrier.

References Cited (Backward Citations)

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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) 1993-04-23 1993-10-23 1994-04-24 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1997-04-23 1997-10-23 1998-04-24 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2001-04-23 2001-10-23 2002-04-24 $7700.00 Window Closed / Lapsed

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