Orally active antiviral compounds

Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...

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514277, 514374, 514438, 514461, 514720, 514721, 546261, 546339, 548237, 549 78, 549502, 568645, C07C 43225, A61K 3144, A61K 3109, C07D21363

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active

055591337

DESCRIPTION:

BRIEF SUMMARY
This application is a 371 of PCT/0592/04-861 filed 06/17/1992.


BACKGROUND

This invention relates to compounds having antiviral activity, pharmaceutical composition containing these antiviral compounds and use of these compounds lot the preparation of a medicament for treating and/or preventing vital infections and methods of treating and/or preventing vital infections, especially picomaviral infections, in mammals using such pharmaceutical compositions.
U.S. Pat. No. 4,851,423 and European Patent Applications EP-A 0274867, and EP-A-0407217, generally, disclose compounds, having antiviral, antiinflammatory and platelet activating factor inhibition activities. The pending European Patent Application discloses such compounds which are represented by the following structural formulas I and II amine salts thereof and pharmaceutically acceptable solvates thereof, wherein substituted phenyl, wherein the substituents are one or more of halogen, lower alkoxy, phenoxy, nitrile, nitro, phenylsulfonyl, loweralkylsulfonyl, oxazol-2-yl, lower alkanoyl, benzoyl, lower alkoxycarbonyl, lower alkyl, phenyl, lower alkylthio, phenylaminothiocarbonyl, or lower alkylaminothiocarbonyl; 4 to 6 membered unsubstituted or substituted heterocyclic ring containing at least one nitrogen in the ring with the remaining members of the ring being at least one carbon, and optionally sulfur or oxygen wherein the substituents are one or more or--COOH, --CH.sub.2 OH, lower alkyl, lower alkylcarbonyl, or aryl lower alkyl; ##STR2## each Q is independently a divalent substituted or unsubstituted, straight or branched chain lower alkanediyl, loweralkanediyl-cycloalkanediyl-lower alkanediyl, lower alkenediyl, lower alkynediyl, phenylene, dihydrofurandiyl, tetrahydrofurandiyl, tetrahydropyrandiyl, lower alkanediyl-tetrahydrofurandiyl-lower alkanediyl wherein the substituents are one or more of hydroxy, epoxy, fluorine, chlorine, azide, or amino; single or fused ring containing from 4 to 10 ring atoms, at least one hetero atom of which is a nitrogen atom and the remaining ring atoms being at least one carbon and optionally sulfur or oxygen, wherein the substituents are one or more of hydroxy, oxo, amino, carbamoyl, carboxyl nitrile, nitro, lower alkyl, lower alkyoxycarbonyl, halogen, sulfamyl, lower alkoxycarbonyllower alkyl, lower alkythio, lower alkoxy, hydroxy lower alkyl, amino lower alkyl, carboxy lower alkyl, guanidino, thioureido, lower alkyl sulfonylamino, aminocarbonyllower alkyl, allyloxycarbonylmethyl or carbamoyloxylower alkyl, with the proviso that W cannot be substituted or unsubstituted isoxazolyl,
However, the compounds of this invention are not specifically disclosed.
European Patent Application EP-A- 0099933 discloses alpha, omega-bis (2-chlorophenoxy)- (C.sub.1 -C.sub.6) alkylene-4, 4'-dicarboxylic acid and its lower alkyl esters which are useful as starting materials for producing polyester fibers or films.
Chem. Ber. 111 (1978) 1108-1125 discloses noncyclic crown ethers with central pyridine units substituted at the 2 and 6 positions with 2 -and 2, 6-substituted phenyloxy methylene donor groups; these crown ethers form stoichiometric crystalline complexes with alkaline and alkaline earth and heavy metal ions.
Chemical Abstracts, Vol. 83 (1975) 163817z discloses p-xylene diphenylether derivatives having fungicidal and herbicidal activities.
European Patent Application EP-A-0028305 discloses substituted diaryl mono-loxy- (but not bisaryloxy) compounds which are active against viruses, especially rhinoviruses.
None of these references disclose the compounds of this invention.


SUMMARY OF THE INVENTION

The present invention provides a compound represented by formula I substituted pyridinyl, the substituents on said phenyl or pyridinyl being independently selected from one, two or three of (C.sub.1 -C.sub.10) alkyl, (C.sub.1 -C.sub.10) perhaloalkyl, (C.sub.1 -C.sub.10) alkoxy, halogen, carbamyl, di (C.sub.1 -C.sub.10) alkylcarbamoyl (C.sub.1 -C.sub.10) alkoxycarbonyl, oxazolinyl, and (C.sub.1 -C.sub.10) alkyl substituted by (C.su

REFERENCES:
patent: 4851423 (1989-07-01), Girijavallabhan et al.
patent: 4891449 (1990-01-01), Borden et al.
patent: 5041604 (1991-08-01), Saito et al.
patent: 5350772 (1994-09-01), Girijavallabhan et al.
Rasshofer, W. et al. Chemische Berichte 1978 vol. III pp. 1108-1125.
CA 83 163816Y, Morikawa, et al. (Japanese 75 09785).
Morikawa, H. et al. Chem Abstracts 1975 vol. 83 Abst #163817z.
Karrer, F. et al. Chem. Absracts 1975 vol. 82 (No. 13) Abst #86207a.
Geratz, J. D. et al. J. Medicinal Chem (1976) vol. 19(#5) 634-639.
Tidwell, R. R. et al. Thrombosis Research (1980) vol. 19 339-349.
Chauhan, P. M. S. et al. Indian Journal of Chemistry (1908) vol. 27B pp. 38-42.

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