Lilly Industries, Inc.

Eli Lilly and Company

Eli Lilly Industries Limited

William B Jamieson

William J Ross

John P Verge

Stephen Richard Baker

Robin G Simmonds

John Christopher Saunders

Roger G Harrison

Alec Todd

Terry D Lindstrom

There are described compounds of formula ##STR1## in which n is 0, 1 or 2, R.sup.1 is a hydrocarbyl group optionally substituted with an optionally substituted phenyl group and containing from 5 to 30 carbon atoms, R.sup.2 is optionally substituted phenyl or C.sub.1-10 alkyl optionally substituted by one or more substituents selected from optionally protected hydroxyl, optionally protected carboxyl, nitrile, optionally protected tetrazolyl, --COR.sup.6 where R.sup.6 is C.sub.1-4 alkyl, C.sub.1-4 alkoxy, an optionally protected amino acid residue or --NR.sub.2.sup.7 where each R.sup.7 is hydrogen or C.sub.1-4 alkyl, and --NHR.sup.8 where R.sup.8 is hydrogen, a protecting group, an optionally protected amino acid residue, C.sub.1-4 alkyl or --COR.sup.9 where R.sup.9 is C.sub.1-4 alkyl or C.sub.1-4 alkoxy, and R.sup.3, R.sup.4 and R.sup.5 are each selected from hydrogen, carboxyl, C.sub.2-5 alkoxycarbonyl, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, hydroxyl, optionally protected tetrazolyl, halo, trifluoromethyl, nitrile, nitro and --CONR.sub.2.sup.10 where each R.sup.10 is hydrogen or C.sub.1-4 alkyl; and salts thereof. The compounds are leukotriene antagonists.

Oxiranes

There are described compounds of the formula ##STR1## in which either R.sup.1 and R.sup.2 are both hydrogen or R.sup.1 is carboxyl and R.sup.2 is hydrogen, C.sub.3-4 alkenyl or C.sub.1-4 alkyl, and R.sup.3, R.sup.4 and R.sup.5 are each hydrogen, nitro, hydroxyl, carboxyl, carboxyC.sub.1-2 alkoxy, C.sub.3-4 alkenyl, C.sub.1-4 alkyl, C.sub.3-4 alkenyloxy, C.sub.1-4 alkoxy or the group ##STR2## where R.sup.6 and R.sup.7 are each hydrogen or C.sub.1-4 alkyl; and salts and esters thereof. The compounds are indicated for use in the treatment of immediate sensitivity reactions and inflammatory diseases.

Certain aurones and their use in the treatment of allergies

There are described pharmacologically active compounds, useful in the treatment of allergic/inflammatory disorders involving SRS-A as causal mediator and which, in free acid form, are of formula I, ##STR1## in which R.sub.1 is (i) an aliphatic, saturated or unsaturated hydrocarbyl radical of up to 20 carbon atoms, unsubstituted or substituted by at least one substituent selected from halogen, hydroxy, C.sub.3-6 alkoxy, C.sub.3-6 cycloalkyl, aryl or heteroaryl, the cycloalkyl, aryl or heteroaryl being unsubstituted or substituted by at least one substituent selected from hydroxy, halogen and alkyl, alkenyl or alkynyl of up to 10 carbon atoms,

SRS-A antagonists

Novel hydantoin compounds are described of the formula (I): ##STR1## wherein Ar is phenyl optionally substituted by up to three radicals selected from the group comprising C.sub.1-6 alkoxy, halogen, 1,3-dioxol-2-yl, hydroxy C.sub.1-4 alkoxy C.sub.1-4 alkyl, phenyl, hydroxyl, nitrile, C.sub.1-4 haloalkyl, C.sub.1-4 alkyl, C.sub.2-4 alkenyloxy, C.sub.1-4 alkoxycarbonyl or phenoxy optionally substituted by C.sub.1-4 haloalkyl, C.sub.1-4 alkoxy or halogen;

Thenyl hydantoins and anti-asthmatic compositions thereof

Substituted aurones of formula (I): ##STR1## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 are the same or different and can each represent hydrogen, halogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.3-8 cycloalkyl, optionally substituted phenyl, C.sub.1-6 haloalkyl, amido, amino, cyano, hydroxy, nitro, C.sub.2-4 alkenyl, carboxyl, tetrazol-5-yl and --CH.dbd.CHCOOH; or

Aurone derivatives

Treatment of immediate hypersensitivity diseases with aryl hydantoins

Pharmaceutical formulations are described, which comprise a hydantoin of formula (I): ##STR1## wherein R.sup.1 is C.sub.1-4 alkyl, R.sup.2 is hydrogen or C.sub.1-4 alkyl; or R.sup.1 and R.sup.2 taken together either represent a C.sub.4-6 alkylene group or a group of formula: ##STR2## where R.sup.5 and R.sup.6 independently represent hydrogen or C.sub.1-4 alkyl;

Method of treating asthma with alkyl, alkylidene and alkylene hydantoins

Hydantoin compounds are described of the formula (I) : ##STR1## wherein R.sup.1 is phenyl, C.sub.1-4 hydroxyalkyl or carboxy C.sub.1-4 alkyl and wherein R.sub.2 is C.sub.1-6 alkyl. The compounds are useful in the prophylactic treatment of immediate hypersensitivity diseases including asthma.

Treating immediate hypersensitivity conditions with 3,5-disubstituted

Acylamino tetrazolyl compounds having anti-allergic activity, methods of making the compounds and pharmaceutical formulations containing the compounds.

Acylamino derivatives

Acylamino pyrazolyl compounds of the formula: ##STR1## wherein Ar represents an optionally substituted pyrazolyl group, the acylamino group --NR.sup.1 COR.sup.2 being attached to a carbon atom of the pyrazolyl ring, which have anti-allergic activity, methods of making the compounds and pharmaceutical formulations containing the compounds.

Acylaminopyrazoles

Phenylpiperazine derivatives of formula (I): ##STR1## where R.sup.1 is benzyl, C.sub.1-6 alkyl or optionally substituted phenyl; R.sup.2 is optionally substituted phenyl; R.sup.3 is hydrogen or C.sub.1-4 alkyl; Q is furan, thiophene, oxazole or thiazole; m is 1 to 3 and n is 0 or 1; and pharmaceutically-acceptable salts thereof are active in the chemotherapy of immediate hypersensitivity conditions such as asthma.

Phenylpiperazine derivatives

1,2,3-triazoles and 1,2,4-triazoles having an N-substituted acylamino substituent are prepared by alkylating N-unsubstituted acylamino triazoles or acylating N-substituted amino triazoles. The N-substituted acylamino triazoles are useful as anti-allergy drugs. Pharmaceutical formulations containing acylamino triazoles and a method of treating allergic conditions utilizing such compounds are provided.

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Woking, United Kingdom

William B Jamieson