Syntex (u.s.a.) Inc.

Angel Guzman

Joseph M Muchowski

Robert J Greenhouse

Pierre Crabbe

David John Morgans, Jr

Eric Brian Sjogren

John H Fried

Jurg R Pfister

Francisco Javier Lopez-Tapia

Todd Richard Elworthy

Saul Jaime-Figueroa

Francisco X Talamas

Gary W Bantle

Arturo Perez-Medrano

Joseph M Muchwoski

Compounds of Formula I: ##STR1## where R.sup.5 is a group selected from Formulae (a), (b), (c) and (d): ##STR2## and the pharmaceutically acceptable salts and N-oxides thereof, are .alpha..sub.1 -adrenergic receptor antagonists useful for the treatment of diseases involving directly or indirectly an obstruction of the lower urinary tract, such as benign prostatic hyperplasia.

Pyrimidinedione, pyrimidinetrione, triazinedione and

Sixteen carbon atom carboxylic acids having 16-phenoxy or 16-phenylthio substituents, and 0, 1, or 4 triple bonds, methods of preparing them, and pharmaceutical preparations containing them. These compounds are useful as lipoxygenase inhibitors.

16-Substituted polyunsaturated hexadecanoic fatty acids

4-Monosubstituted and 4,6-disubstituted phenoxazines, methods of preparing them and pharmaceutical compositions containing them. These compounds are useful as anti-inflammatories.

4-monosubstituted and 4,6-disubstituted

Thiol esters of 4,5-allenyl prostaglandins, methods of making them, and pharmaceutical compositions containing them. These compounds are useful as gastric acid secretion inhibitors.

Thiol esters of 4,5-allenyl prostaglandins and use thereof as

4-Monosubstitued and 4,6-disubstituted phenoxazines, methods of preparing them and pharmaceutical compositions containing them. These compounds are useful as anti-inflammatories.

4-monosubstituted and 4,6-disubstituted phenoxazines

Long chain unsaturated hydrocarbon derivatives, having from 13 to 21 carbon atoms, which are substituted at the 1-position by a phenoxy, phenylthio or a phenyl that bear a carboxylic acid group at the ortho, meta or para positions, and up to 4 carbon-carbon triple bonds, methods of preparing them, and pharmaceutical preparations containing them. These compounds are useful as lipoxygenase inhibitors, and therefore as antiinflammatory agents.

Arachidonic acid analogs

Compounds of the formula: ##STR1## and the pharmaceutically acceptable, non-toxic salts and esters (alkyl, 1-6C) thereof, wherein:

Thiazolidin-2-one analogs

This invention relates to novel imidazolidinone prostaglandin compounds of the formula ##STR1## and the pharmaceutically acceptable salts thereof, wherein R.sup.1 and R.sup.2 are independently hydrogen or alkyl of 1 to 4 carbons; R.sup.3 is hydrogen or methyl; and R4 is --(CH.sub.2).sub.n CH.sub.3 wherein n is 3-7, cycloalkyl of 5-7 carbons, a substituent of the formula ##STR2## wherein R.sup.5 is hydrogen, alkyl of 1 to 4 carbons, alkoxy of 1 to 4 carbons, halo or trifluoromethyl. These compounds are inhibitors of blood platelet aggregation.

Imidazolidinone prostaglandins, compositions and use

Oxazolidin-2-one prostaglandin compounds

Novel prostaglandin dehydro analogs of the PGA and PGB series and the 9-hydroxy-derivatives thereof, which possess a diethylenic unsaturation in the carboxylic acid chain and may be additionally substituted at C-4, C-6, C-9 and/or C-15 by a methyl, ethyl or propyl group, as well as the C-20-nor, bisnor or C-20 alkyl derivatives thereof, the alkyl group being of a straight chain and containing from 1 to 5 carbon atoms inclusive,, and processes for making same. 9-keto-15.alpha.-hydroxyprosta-4,5,10,13-trans-tetraenoic acid and 9-keto-15.alpha.-hydroxyprosta-4,5,8(12),13-trans-tetraenoic acid are representative of the class. Also included are the pharmaceutically acceptable, non toxic esters and salts of the carboxylic acid function and the pharmaceutically acceptable, non toxic esters and/or ethers of the secondary hydroxyl groups. These compounds possess prostaglandin-like activities and thus are useful in the treatment of mammals, where prostaglandins are indicated.

Polyunsaturated prostaglandin derivatives

Prostaglandin analogs of the PGF.sub.2.sub..alpha., PGE.sub.2, PGF.sub.1.sub..alpha. and PGE.sub.1 series substituted at C-10.alpha. by a hydroxyl group, the derivatives of the PGF.sub.1.sub..alpha. and PGE.sub.1 series further substituted at C-5,6 by a methylene or dihalomethylene group, and the 10,11-ketals thereof and methods of preparing such compounds. 9.alpha.,15.alpha.-Dihydroxy-10.alpha.,11.alpha.-isopropylidenedioxyprosta -5,13-dienoic acid, 9-keto-10.alpha.,11.alpha.-isopropylidenedioxy-15.alpha.-hydroxyprosta-5,1 3-dienoic acid and 5,6-methylene-9.alpha.,15.alpha.-dihydroxy-10.alpha.,11.alpha.-isopropylid enedioxyprost-13-enoic acid are representative of the class. Also included are the corresponding esters, ethers, pharmaceutically acceptable salts and amides. These compounds possess prostaglandin-like activity and thus are useful in the treatment of mammals, where prostaglandins are indicated.

Substituted prostaglandin derivatives

Novel 8R-antimeric and racemic 11.alpha.-methylsubstituted-prosta-5-cis, 13-trans-dienoic and prost-13-trans-enoic acids having oxygenated functions at the C-9 and C-15 positions of the molecule, as well as the 15-methyl or ethyl derivatives thereof and processes for making such compounds. Also encompassed are the pharmaceutically acceptable, non-toxic alkyl esters and salts of the carboxylic acid function of these novel compounds.

11.alpha.-METHYLSUBSTITUTED PROSTAGLANDIN DERIVATIVES

Novel process for the preparation of 11.alpha.-hydroxymethyl derivatives of natural (8R-) and racemic 9-keto-15.alpha.-hydroxy- and 9,15.alpha.-dihydroxy-prosta-5-cis,13-trans-dienoic and prost-13-transenoic acids, and the novel 15-methyl and ethyl substituted derivatives thereof, as well as the esters of the primary and secondary hydroxy groups and the non-toxic, pharmaceutically acceptable salts of the novel compounds.

Growing community of inventors

Mexico City, Mexico

Angel Guzman