Quinoline derivatives and their use as antagonists of leukotrien

Details Quinoline derivatives and their use as antagonists of leukotrien Quinoline derivatives and their use as antagonists of leukotrien

1990-04-20

1991-10-22

Springer, David B.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Having -c-, wherein x is chalcogen, bonded directly to...

514311, 546472, 546174, 546176, C07D40110, C07D21512, A61K 3141, A61K 3147

Patent

active

050596101

DESCRIPTION:

BRIEF SUMMARY
FIELD OF INVENTION

This invention relates to quinolinyl phenyl compounds and their use as valuable pharmaceutical agents, particularly as lipoxygenase inhibitors and/or leukotriene antagonists possessing anti-inflammatory and anti-allergic properties.


SUMMARY OF THE INVENTION

This invention relates to the compounds described by the general Formula I and to therapeutic compositions comprising as active ingredient a compound of Formula I: ##STR1## where: A is O or S; ##STR2## D is O, S, NR.sub.1, ##STR3## or a chemical bond; E is a chemical bond or ##STR4## a is 0-2; b is 0-1; halo, nitro, haloalkyl, cyano or acyl; aralkoxy, amino, mono-and di-alkylamino, aralkylamino, acylamino, carbamyl, carboxy, carbalkoxy, tetrazolyl, or acylsulfonamido; thus forming a 3-6 membered ring; --(CH.sub.2).sub.z --, where z is 2 to 5; alkylidenyl substituent, .dbd.CHR.sub.1 ; ##STR5## --OR.sub.1, tetrazolyl or substituted tetrazolyl where the substituent may be alkyl, carboxyalkyl or carbalkoxyalkyl; pharmaceutically acceptable salts thereof.
The compounds of Formula I contain at least three aromatic rings, which may be designated as shown in Formula II below, and for which their substitution pattern along the chain with respect to each other is shown also below. ##STR6##
The substitution pattern of the quinoline ring, that is Ring I, is preferably at the 2- position for extending the side chain. As this side chain progresses from the quinoline ring, the two phenyl rings, designated Ring II and Ring III may be substituted along the chain in the ortho, meta or para positions with respect to each other and Ring II may also be substituted in the ortho, meta and para positions in respect to the quinoline ring.
The preferred substitution pattern for ring II is meta or para, that is: ##STR7##
Ring III may be substituted equally in the ortho, meta or para positions, that is: ##STR8##
Further preferred compounds of this invention are described by Formula V below: ##STR9##
where c+d=1-3 and R, R.sub.1, R.sub.2, e, f, n, D, E and Z are as described above.
The preferred compounds of Formula V are those where Z is --COOR.sub.1 ; --CN; ##STR10## or tetrazolyl.
In addition, the present invention relates to the method of using these compounds as lipoxygenase inhibitors and/or leukotriene antagonists possessing anti-inflammatory and anti-allergic properties.
As employed above and throughout the disclosure, the following terms, unless otherwise indicated, shall be understood to have the following meanings:
"Alkyl", either alone or with various substituents defined herein, means a saturated aliphatic hydrocarbon, either branched or straight chained. A "loweralkyl" is preferred having about 1 to about 6 carbon atoms. Examples of alkyl include methyl, ethyl, n-propyl, isopropyl, butyl, sec-butyl, t-butyl, amyl, hexyl, etc.
"Alkoxy" refers to a loweralkyl-O-group.
"Alkenyl" refers to a hydrocarbon having at least one point of unsaturation and may be branched or straight chained. Preferred alkenyl groups have six or less carbon atoms and include vinyl, allyl, ethynyl, isopropenyl, etc.
"Aralkyl" means an alkyl group substituted by an aryl radical. The preferred aralkyl groups are benzyl or phenethyl.
"Cycloalkyl" means a saturated monocyclic hydrocarbon ring having 3 to about 6 carbon atoms. Preferred groups include cyclopropyl, cyclohexyl, etc.
"Acyl" means an organic radical derived from an organic acid by removal of its hydroxyl group. Preferred acyl groups are groups derived from carboxylic acids. More preferred are the lower alkanoyl or benzoyl groups such as acetyl, propionyl benzoyl, etc.
"Halo" means a halogen. Preferred halogens include, chloride, bromide and fluoride. The preferred haloalkyl group is trifluromethyl.
The compounds of this invention may be prepared in segments as is common to a long chain molecule. Thus it is convenient to synthesize these molecules by employing condensation reactions at the A, B and D cites of the molecule. For this reason the present compounds may be prepared by art recognized procedures from known co

REFERENCES:
patent: 4920130 (1990-04-01), Huang et al.
patent: 4920131 (1990-04-01), Huang et al.
patent: 4920132 (1990-04-01), Huang et al.
patent: 4920133 (1990-04-01), Huang et al.

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