Pharmaceutically active compounds

Details Pharmaceutically active compounds Pharmaceutically active compounds

1991-12-18

1993-12-21

Ford, John M.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

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

514395, 514374, 514376, 514377, 548235, 548236, 5483044, 5483047, 5483051, 5483061, 5483097, 5483101, 5483104, C07D40112, C07D23506, A61K 31415

Patent

active

052721671

DESCRIPTION:

BRIEF SUMMARY
This invention relates to compounds with pharmaceutical activity, i.e. antiviral, antiinflammatory and platelet activating factor inhibition, their pharmaceutically acceptable salts and solvates and pharmaceutical compositions containing the active compounds.
Arildone, a compound represented by the formula ##STR2## is active in vitro against herpes virus and polio virus, but is only marginally active against rhinoviruses. Diana et al., J. Med. Chem. 28, 748 (1985) prepared some alkyl-substituted isoxazole analogs of arildone in an attempt to prepare compounds with broad spectrum activity against picornaviruses. Some of the compounds were active against both rhinovirus type 2 and poliovirus type 2. However, there is no indication that any of the Diana et al. compounds have activity as antiinflammatories or as platelet activating factor inhibitors. Many of the compounds of this invention possess such activity. The following publications are also cited: EPA 86043; U.S. Pat. No. 4,540,703; EPA 49060; U.S. Pat. No. 3,190,883; EPA 112292; EPS 2158543; and EPA 274867 as well as J. Med. Chem. 28 (1985) pages 748-752.
The compounds of this invention are represented by the following structural formulas I and II ##STR3## pharmaceutically acceptable acid addition, basic addition, and quaternary amine salts thereof and pharmaceutically acceptable solvates thereof, wherein
each Z is independently tertiary butyl; phenyl; naphthyl; adamantanyl; 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, lower alkylaminothiocarbonyl, hydroxyiminoloweralkyl, hydroxyloweralkyl or carbamyl; or 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 of --COOH, --CH.sub.2 OH, lower alkyl, loweralkylcarbonyl, or aryl lower alkyl;
X and Y are each independently a bond, ##STR4##
each Q is independently a divalent substituted or unsubstituted, straight or branched chain lower alkanediyl, loweralkanediyl-cycloalkanediylloweralkanediyl, lower alkenediyl, lower alkynediyl, phenylene, dihydrofurandiyl, loweralkanediyldihydrofurandiyl-loweralkanedily, tetrahydrofurandiyl, tetrahydropyrandiyl, loweralkanediyl-tetrahydropyrandiylloweralkanediyl, loweralkanediyl-tetrahydrofurandiylloweralkanediyl wherein the substituents are one or more of hydroxy, ketalized adjacent hydroxys (see, for example, Example 91), epoxy, fluorine, chlorine, azide, or amino;
W is a monovalent substituted or unsubstituted aryl group, wherein the substituents on the aryl group are as defined above for Z wherein Z is substituted phenyl, or an unsubstituted or substituted heterocyclic 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 on the heterocyclic ring are one or more of hydroxy, oxo, amino, carbamoyl, carboxyl, nitrile, nitro, lower alkyl, loweralkoxycarbonyl, halogen, sulfamyl, loweralkoxycarbonylloweralkyl, loweralkythio, lower alkoxy, hydroxy loweralkyl, amino loweralkyl, carboxy loweralkyl, guanidino, thioureido, lower alkyl sulfonylamino.-aminocarbonylloweralkyl, allyloxycarbonylmethyl or carbamoyloxyloweralkyl, with the proviso that W cannot be substituted or unsubstituted isoxazolyl, and with the further proviso that when Z is 2-chloro-4-methoxyphenyl, X is --O--, Q is C.sub.5 --C.sub.7 alkanediyl and Y is a bond, W is not imidazolyl substituted at positions 2, 4 and 5 with 1-3 substituents independently selected from the group consisting of hydrogen, hydroxyloweralkyl, nitro, loweralkoxycarbonyl, lower alkyl and amino methylene;
W' is divalent W.
The invention also includes pharmaceutical

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