Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1995-08-16
1997-01-07
Springer, David B.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546174, 546176, 546180, C07D40310, C07D40710, A61K 3147
Patent
active
055917526
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP94/00234 filed Feb. 16, 1994, and published as WO94/19345 Sep. 1, 1994.
TECHNICAL FIELD
This invention relates to a quinoline derivative and a salt thereof which have a thromboxane A.sub.2 antagonistic action, a thromboxane A2-synthesizing enzyme inhibitory action and so on as well as a leukotriene D.sub.4 antagonistic action and are useful as an antiallergic medicine and an anti-inflammatory medicine.
BACKGROUND ART
As a compound having a leukotriene D.sub.4 antagonistic action as in the present invention and having a structure partially Similar to that of the compound of the present invention, there have been known, for example, 5-[3-[3-(2-quinolinylmethoxy)phenoxy]propyl]-1H-tetrazole (RG7152; J. Med. Chem. 1990, 33, 1186), 5-[[2-[[4-(2-quinolinylmethoxy)phenoxy]methyl]phenyl]methyl]-1H-tetrazole (RG12525; J. Med. Chem. 1990, 33, 1194), etc.
DISCLOSURE OF THE INVENTION
The present inventors have studied for many years in order to develop a compound having a strong leukotriene D.sub.4 antagonistic action, and having a thromboxane A.sub.2 antagonistic action, a thromboxane A.sub.2 -synthesizing enzyme inhibitory action, etc. as well as a leukotriene D.sub.4 antagonistic action so that it can be an antiallergic medicine and an anti-inflammatory medicine which are clinically useful, and consequently found that a novel quinoline derivative having a dihydrodibenzoxepine skeleton in a molecule satisfies this object, to accomplish the present invention.
The present invention is a quinoline derivative represented by the formula (I): ##STR2## [wherein R.sup.1 represents a group selected from a halogen atom, a lower alkyl group, a halogeno-lower alkyl group, a lower alkoxy group, a halogeno-lower alkoxy group, a lower alkylthio group and a halogeno-lower alkylthio group, m represents 0 or an integer of 1 to 4 and when m is 2 to 4, R.sup.1 s may be different from each other. R.sup.2 represents a group selected from a halogen atom, a hydroxyl group, a nitro group, a cyano group, a carbamoyl group, a carboxy group, a tetrazol-5-yl group, a lower alkyl group or a lower alkoxy group or a lower alkylthio group which may be substituted by carboxy or tetrazol-5-yl, and an alkanoyl-lower alkyl group, n represents 0 or an integer of 1 to 4 and when n is 2 to 4, R.sup.2 s may be different from each other. X represents an oxygen atom, a sulfur atom, a methylene group, a formula of .dbd.CH-- or a formula of .dbd.N--O--. Y represents a straight or branched alkylene group. Z represents a carboxy group, a tetrazol-5-yl group, a (tetrazol-5-yl)aminocarbonyl group, a (tetrazol-5-yl)carbonylamino group, a formula of --NH--CO--R.sup.3, a formula of --NH--SO.sub.2 --R.sup.3 or a formula of --CO--NH--SO.sub.2 --R.sup.3 (wherein R.sup.3 represents a lower alkyl group which may be substituted by a halogen, or a phenyl group which may be substituted by a halogen, a lower alkyl, a halogeno-lower alkyl, a lower alkoxy, a halogeno-lower alkoxy, nitro, cyano, carboxy or tetrazol-5-yl). p represents 0 or 1. .......... represents a single bond or a double bond] and a salt thereof.
In the compound represented by the above formula (I), the substituent R.sup.1 in the formula is a group selected from a) a halogen atom, b) a lower alkyl group, c) a halogeno-lower alkyl group, d) a lower alkoxy group, e) a halogeno-lower alkoxy group, f) a lower alkylthio group and g) a halogeno-lower alkylthio group.
In R.sup.1, as the halogen atom, there may be mentioned fluorine, chlorine, bromine and iodine; as the lower alkyl group, a C.sub.1 to C.sub.4 alkyl group such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl and t-butyl; as the halogeno-lower alkyl group, a halogeno-C.sub.1 to C.sub.4 alkyl group such as fluoromethyl, difluoromethyl, trifluoromethyl, trichloromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2,2,2-trifluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 3-chloropropyl, 3-bromopropyl, 3-iodopropyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl and 4-iodobutyl; as the lower alkoxy group, a
REFERENCES:
patent: 4396550 (1983-08-01), Takizawa et al.
patent: 4999363 (1991-03-01), Oshima et al.
patent: 5010087 (1991-04-01), Oshima et al.
Fujiwara Hiroshi
Ikuta Takashi
Kaku Yoshio
Kimura Tomio
Okanari Eiji
Springer David B.
Ube Industries Ltd.
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