Lilly Industries, Inc.

Eli Lilly and Company

Eli Lilly Industries Limited

William J Ross

John P Verge

William B Jamieson

Alec Todd

Stephen Richard Baker

Barry P Clark

Delme Evans

William R Williamson

Robin G Simmonds

Michael Ralph Jolley

Brian Picton Swann

John Christopher Saunders

Roger G Harrison

John Goldsworthy

Terry D Lindstrom

Alex Todd

There is disclosed a pharmaceutical compound of the formula ##STR1## in which R.sup.1 is C.sub.7-20 alkyl, C.sub.7-20 alkenyl, or C.sub.7-20 alkynyl, the alkyl, alkenyl or alkynyl group being optionally substituted by phenyl or substituted phenyl, R.sup.2 is --CN, --COOR.sup.3 or ##STR2## wherein R.sup.3 is hydrogen or a protecting group, X is alkylene containing 1 to 6 carbon atoms and Y is a nitrogen-containing group selected from ##STR3## where each R.sup.4 independently is hydrogen or C.sub.1-4 alkyl; and salts thereof.

Tetrazole compounds and use as anti-allergics

Pharmaceutical compounds are described of the formula ##STR1## in which R.sup.1 is (i) R.sup.4 O(CH.sub.2 CH.sub.2 O).sub.n (CH.sub.2).sub.m --, where R.sup.4 is hydrogen or C.sub.1-5 alkyl, n is 0 or 1 to 5 and m is 1 to 7, or (ii) R.sup.5 --X-- where R.sup.5 is a polar group and X is a C.sub.6-20 alkylene or a C.sub.6-20 alkenylene radical containing from 1 to 3 double bonds, R.sup.2 is a group of the formula A--B-- where A is --COOH or ##STR2## where R.sup.6 is hydrogen or a protecting group, and B is C.sub.1-6 alkylene, and R.sup.3 is --COOH or ##STR3## where R.sup.7 is hydrogen or a protecting group; or a salt or ester thereof.

Sulfur containing alkenylenyl substituted benzoic acids and phenyl

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

Compounds are described of the formula ##STR1## in which R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano, 5-tetrazolyl or R.sup.6, where R.sup.5 is hydrogen or C.sub.1-8 alkyl and R.sup.6 is phenyl or naphthyl, the phenyl or naphthyl group being optionally substituted by one or more group selected from halogen, C.sub.1-6 alkyl, C.sub.1-4 alkoxy, hydroxy, benzyloxy, nitro, trifluoromethyl, carboxyl, C.sub.1-4 alkylsulphinyl, C.sub.1-4 alkylsulphonyl, N(R.sup.5).sub.2, NHCOR.sup.5 and SR.sup.5 ; R.sup.2 is R.sup.6 or --CH.dbd.CH--R.sup.6 when R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano or 5-tetrazolyl, or R.sup.2 is --CH.dbd.CH--R.sup.6 when R.sup.1 is R.sup.6 ; R.sup.3 is hydrogen, C.sub.1-6 alkyl, halogen, hydroxy or --OCH.sub.2 R.sup.6 ; and R.sup.4 is hydrogen, C.sub.1-6 alkyl or halogen; and salts thereof. The compounds have pharmaceutical properties and in particular are useful in the treatment of immediate hypersensitivity conditions such as asthma.

6-Substituted pyranone compounds and their use as pharmaceuticals

Compounds of the following formula are described: ##STR1## in which n is 0, 1 or 2, R.sup.1 is C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.1-4 alkylthio, C.sub.1-4 alkylsulphonyl, trifluoromethyl, halo or nitro, and R.sup.2 and R.sup.3 are each independently hydrogen or C.sub.1-4 alkyl, and salts thereof. The compounds are useful in the treatment of immediate hypersensitivity conditions and are prepared by reaction of the appropriate formylquinolone with malonic acid, ylid or phosphonate.

Quinolone derivatives and their use in a method of controlling an

Compounds are described of the formula ##STR1## in which R.sup.1 is COOR.sup.5, CONHR.sup.5, cyano, 5-tetrazolyl or 5-tetrazolylaminocarbonyl, where R.sup.5 is hydrogen or C.sub.1-6 alkyl; R.sup.2 is hydrogen or C.sub.1-6 alkyl; R.sup.3 is a group of the formula

5-Substituted pyranone compounds and their use as pharmaceuticals to

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

A class of novel 2-oxazolyl ureas and carbamates having anti-allergic activity are described together with methods of making such compounds and pharmaceutical compositions containing the active compounds of the invention.

Oxazole carbamates, formulations and asthma treatment

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.

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Lightwater, United Kingdom

William J Ross