Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1990-06-01
1992-05-05
Springer, David B.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
5142325, 514314, 546174, 546176, 544128, C07D40310, C07D41310, A61K 3147
Patent
active
051108194
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to hitherto unknown compounds useful in the human and veterinary therapy, to pharmaceutically acceptable salts thereof, to bioreversible derivatives thereof, to methods for producing said new compounds, to pharmaceutical compositions containing the new compounds, to dosage units of the compositions, and to methods of treating patients using said compositions and dosage units.
It has recently been discovered that leukotrienes, which are formed via the 5-lipoxygenase pathway of arachidonic acid metabolism, are implicated in a variety of pathophysiologic functions, such as bronchoconstriction, plasma exudation, coronary artery spasm, leukocyte chemotaxis and neutrophil degranulation (1). It is therefore of considerable interest to develop compounds which inhibit 5-lipoxygenases and thereby the production of leukotrienes, or antagonize the effects of leukotrienes.
German patent application DE 3607 382 (corresponding to United Kingdom patent application No. 8604183) describes a series of pyridylmethoxy or -methyl-thio substituted N-substituted aniline derivatives with activities as lipoxygenase inhibitors and/or leukotriene antagonists. The N-substituent in these compounds may be substituted or unsubstituted aryl or aralkyl.
EP-A-206751 discloses compounds having the formula: ##STR1## In this formula Y inter alia may be CH.sub.2 O, X is O, S, SO, SO.sub.2 or NR.sub.2 and R.sup.3 inter alia may be a saturated or unsaturated aliphatic group which may be substituted by a carboxyl group. These compouns are described to antagonize the effects of the leucotrienes and to inhibit the leucotrienes. Thus, these compounds are valuable in the prevention and treatment of disease states in which the leucotrienes are the causative factor.
EP-A-190 722 discloses compounds of the formula: ##STR2## in which X is inter alia CH.sub.2 O, Z is an alkylene chain containing up to 10 carbon atoms in the principal chain which may be attached to the phenyl group through an oxygen atom and R may be OR.sub.6 wherein R.sub.6 is H, lower alkyl or phenyl. These compounds are lipoxygenase inhibitors possessing anti-inflammatory and anti-allergic activities.
EP-A-232 954 discloses compounds of the general formula: ##STR3## in which inter alia X may be an nitrogen atom and W a carbon atom, Y may be CH.sub.2 O, R.sub.2 is hydrogen oder lower alkyl and R.sub.3 is lower alkyl, perfluoro lower alkyl or perfluorophenyl. These compounds are useful in the treatment of leukotriene-mediated naso-bronchial obstructive air passage way conditions, such as allergic rhinitis, allergic bronchial asthma and the like, and anti-thrombotic therapy.
EP-A-233 763 discloses compounds of the formula: ##STR4## in which inter alia Y is CH.sub.2 O, and X.sup.2 and X.sup.3 are independently O, S, SO or SO.sub.2 and R.sup.6 is H or C.sub.1 bis C.sub.4 alkyl. The residues attached to X.sub.2 and X.sub.3 may be saturated or unsaturated aliphatic groups which may be inter alia substituted by a carboxyl group. These compounds are leukotriene antagonists or inhibitors and are useful for treatment of disease states in which the leukotrienes are the causative factor.
EP-A-271 287 has a similar disclosure.
Now it has surprisingly turned out that introduction of one of a number of acidic groups into such N-substituents results in compounds with an even more pronounced effect.
Furthermore, it has been found that in the presence of such acidic groups also compounds which are not anilines, but in which the nitrogen atom has been separated from the phenyl group with a carbon chain are potent compounds.
Moreover, these compounds are more specific agents, as their leukotriene antagonistic activity is much more pronounced than their activity as lipoxygenase inhibitors.
Also, the present compounds are well absorbed after enteral administration.
The present compounds have the formula I ##STR5## in which formula I R.sub.1 stands for hydrogen, straight or branched, saturated or unsaturated, unsubstituted or substituted C.sub.1 -C.sub.8 -alkyl, aryl or for ar-C.su
REFERENCES:
patent: 4826987 (1989-05-01), Nielsen et al.
patent: 4904786 (1990-02-01), Musser et al.
patent: 4929626 (1990-05-01), Mohrs et al.
Ahnfelt-Ronne Ian
Hansen Erik T.
Kirstein Dorte
Nielsen Ole Bent I.
Rachlin Schneur
Leo Pharmaceutical Products Ltd.
Springer David B.
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