Abstract: d1- and 8R-9-fluoro-11,15.alpha.-dihydroxyprosta-5-cis,13-trans-dienoic acid, d1- and 8R-9-fluoro-11,15.alpha.-dihydroxy-15.beta.-methyl-prosta-5-cis,13-trans-d ienoic acid and d1- and 8R-9-fluoro-11,15.beta.-dihydroxy-15.alpha.-methylprosta-5-cis,13-trans-di enoic acid, the pharmaceutically acceptable, nontoxic lower alkyl esters and salts thereof and process for the production of such compounds. 8R-9.beta.-fluoro-11.alpha.,15.alpha.-dihydroxyprosta-5-cis,13-trans-dieno ic acid is a representative compound of the class. These compounds possess prostaglandin-like activities and thus are useful in the treatment of mammals where prostaglandins are indicated. They are particularly useful as luteolytic agents in female mammals and as bronchodilators.
Type:
Grant
Filed:
June 26, 1975
Date of Patent:
December 14, 1976
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Joseph M. Muchowski, Esperanza V. Velarde
Abstract: Compositions containing and methods employing, as the essential ingredient, novel disubstituted xanthone carboxylic acid compounds which are useful in the treatment of allergic conditions. Methods for preparing these compounds and compositions and intermediates therein are also disclosed. 5-Methylsulfinyl-7-isopropoxyxanthone-2-carboxylic acid and 5,7-di(methylsulfinyl)xanthone-2-carboxylic acid are illustrated as representative compounds.
Type:
Grant
Filed:
December 4, 1975
Date of Patent:
November 2, 1976
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Jurg R. Pfister, Ian T. Harrison, John H. Fried
Abstract: Compositions containing and methods employing, as the essential ingredient, novel disubstituted xanthone carboxylic acid compounds which are useful in the treatment of allergic conditions. Methods for preparing these compounds and compositions and intermediates therein are also disclosed. 5-Methylsulfinyl-7-isopropoxyxanthone-2-carboxylic acid and 5,7-di(methylsulfinyl)xanthone-2-carboxylic acid are illustrated as representative compounds.
Type:
Grant
Filed:
December 4, 1975
Date of Patent:
November 2, 1976
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Jurg R. Pfister, Ian T. Harrison, John H. Fried
Abstract: Compositions containing and methods employing, as the essential ingredient, novel disubstituted xanthone carboxylic acid compounds which are useful in the treatment of allergic conditions. Methods for preparing these compounds and compositions and intermediates therein are also disclosed. 5-Methylsulfinyl-7-isopropoxyxanthone-2-carboxylic acid and 5,7-di(methylsulfinyl)xanthone-2-carboxylic acid are illustrated as representative compounds.
Type:
Grant
Filed:
December 4, 1975
Date of Patent:
October 26, 1976
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Jurg R. Pfister, Ian T. Harrison, John H. Fried
Abstract: Novel racemic and 8R-antimeric 16-phenoxy- and 16-(o, m or p)-substituted phenoxy derivatives of 9.alpha., 11.alpha.,15-trihydroxy-17,18,19,20-tetranorprosta-4,5,13-trans-trienoic acids, which may be further substituted at C-15 by a methyl or ethyl group, the pharmaceutically acceptable, non-toxic lower alkyl esters and salts thereof and processes for the production of such compounds. dl 9.alpha.,11.alpha.,15.alpha.-trihydroxy-16-m-trifluoromethylphenoxy-17,18, 19,20-tetranorprosta-4,5,13-trans-trienoic acid and dl 9.alpha.,11.alpha.,15 -trihydroxy-15 -methyl-16-m-trifluoromethylphenoxy-17,18,19,20-tetranorprosta-4,5,13-tran s-trienoic acid are representative compounds of the class. These compounds possess prostaglandin-like activities and thus are useful in the treatment of mammals where prostaglandins are indicated. They are particularly useful as luteolytic agents in female mammals.
Abstract: Compositions containing and methods employing, as the essential ingredient, novel disubstituted xanthone carboxylic acid compounds which are useful in the treatment of allergic conditions. Methods for preparing these compounds and compositions and intermediates therein are also disclosed. 5-Isopropyl-7-acetylxanthone-2-carboxylic acid is illustrated as a representative compound.
Type:
Grant
Filed:
December 4, 1975
Date of Patent:
September 7, 1976
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Jurg R. Pfister, Ian T. Harrison, John H. Fried
Abstract: Novel 2-substituted-1,2,4-thiadiazolo-[2,3-a]-imidazoles of the formula ##SPC1##And the pharmaceutically acceptable salts thereof; and process for their preparation. These 2-substituted-1,2,4-thiadiazolo-[2,3-a]-imidazoles are useful as fungistatic and fungicidal agents.
Abstract: Novel 2-substituted-1,2,4-thiadiazolo-[2,3-a]-benzimidazoles of the formula ##SPC1##And the pharmaceutically acceptable salts thereof; and process for their preparation. These 2-substituted-1,2,4-thiadiazolo-[2,3-a]-benzimidazoles are useful as fungistatic and fungicidal agents.
Abstract: (d1)-13-Substituted sulfinyl-prostaglandin-like [(d1)-2.alpha.-substituted-3.beta.-(1.alpha.-substituted sulfinyl-trans-2-alkenyl)-1-oxygenated cyclopentane and (d1)-2.alpha.-substituted-3.beta.-(1.alpha.-substituted sulfinyl-trans-2-alkenyl-4.alpha.-hydroxy-1-oxygenated cyclopentane]compounds exhibiting prostaglandin-like biological properties are prepared from known prostaglandins and prostaglandin-like compounds.
Abstract: (dl)-13-Substituted sulfinyl-prostaglandin-like [(dl)-2.alpha.-substituted-3.beta.-(1.alpha.-substituted sulfinyl-trans-2-alkenyl)-1-oxygenated cyclopentane and (dl)-2.alpha.-substituted -3.beta.-(1.alpha.-substituted sulfinyl-trans-2-alkenyl)-4-oxygenated-1-oxygenated cyclopentane] compounds exhibit prostaglandin-like biological properties and are also useful intermediates in the preparation of known prostaglandins.
Abstract: 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.
Type:
Grant
Filed:
July 15, 1974
Date of Patent:
July 20, 1976
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Pierre Crabbe, John H. Fried, Angel Guzman
Abstract: Compositions containing and methods employing, as the essential ingredient, novel disubstituted xanthone carboxylic acid compounds which are useful in the treatment of allergic conditions. Methods for preparing these compounds and compositions and intermediates therein are also disclosed. 5-Methyl-sulfinyl-7-isopropoxyxanthone-2-carboxylic acid and 5,7-di(methylsulfinyl)xanthone-2-carboxylic acid are illustrated as representative compounds.
Type:
Grant
Filed:
March 13, 1975
Date of Patent:
June 22, 1976
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Jurg R. Pfister, Ian T. Harrison, John H. Fried
Abstract: Compositions containing and methods employing, as the essential ingredient, novel disubstituted xanthone carboxylic acid compounds which are useful in the treatment of allergic conditions. Methods for preparing these compounds and compositions and intermediates therein are also disclosed. 5-Methylsulfinyl-7-isopropoxyxanthone-2-carboxylic acid and 5,7-di(methylsulfinyl)xanthone-2-carboxylic acid are illustrated as representative compounds.
Type:
Grant
Filed:
March 13, 1975
Date of Patent:
June 15, 1976
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Jurg R. Pfister, Ian T. Harrison, John H. Fried
Abstract: Compositions containing and methods employing, as the essential ingredient, novel disubstituted xanthone carboxylic acid compounds which are useful in the treatment of allergic conditions. Methods for preparing these compounds and compositions and intermediates therein are also disclosed. 5-Methyl-sulfinyl-7-isopropoxyxanthone-2-carboxylic acid and 5,7-di(methylsulfinyl)xanthone-2-carboxylic acid are illustrated as representative compounds.
Type:
Grant
Filed:
March 13, 1975
Date of Patent:
June 15, 1976
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Jurg R. Pfister, Ian T. Harrison, John H. Fried
Abstract: Method for immunizing nursing piglets against transmissible gastroenteritis (TGE) virus by administering to the pregnant sow an effective amount of a vaccine containing attenuated TGE virus and permitting the nursing piglets to suckle the sow. The vaccine is administered twice, (a) intramuscularly at from about 63 days to about 21 days pre-farrowing and (b) intranasally at from about 21 days to about 7 days pre-farrowing, with the proviso that at least 14 days and not more than 42 days elapse between the intranasal and intramuscular inoculations.
Abstract: 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.
Abstract: Compositions containing and methods employing, as the essential ingredient, novel disubstituted xanthone carboxylic acid compounds which are useful in the treatment of allergic conditions. Methods for preparing these compounds and compositions and intermediates therein are also disclosed. 5-Methylthio-7-isopropoxyxanthone-2-carboxylic acid and 5,7-di-(methylthio)xanthone-2-carboxylic acid are illustrated as representative compounds.
Type:
Grant
Filed:
January 20, 1975
Date of Patent:
April 20, 1976
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Jurg R. Pfister, Ian T. Harrison, John H. Fried
Abstract: Compositions containing and methods employing, as the essential ingredient, novel substituted xanthone carboxylic acid compounds which are useful in the treatment of allergic conditions. Methods for preparing these compounds and compositions and intermediates therein are also disclosed. 6-Acetylxanthone-2-carboxylic acid is illustrated as a representative compound.
Type:
Grant
Filed:
January 23, 1975
Date of Patent:
April 6, 1976
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Jurg R. Pfister, Ian T. Harrison, John H. Fried
Abstract: Novel 2-substituted-1,2,4-thiadiazolo-[ 2,3-a]-benzimidazoles of the formula ##SPC1##And the pharmaceutically acceptable salts thereof; and process for their preparation. These 2-substituted-1,2,4-thiadiazole-[2,3-a]-benzimidazoles are useful as fungistatic and fungicidal agents.