Abstract: 1-Alkylamino-3-(5-alkynylaminocarbonylthiazol-2-yloxy)-2-propanol; 5-(5-alkynylaminocarbonyl-thiazol-2-yloxymethylene)-N-alkyloxazolidine and/or 2-substituted oxazolidine derivatives thereof, and methods of making such compounds. The compounds exhibit cardiovascular activity and are useful in the treatment of abnormal heart conditions in mammals. The compounds are also useful in the treatment of hypertension in mammals. The 5-(5-alkynyl-aminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidines and derivatives are also intermediates for the 1-alkylamino-3-(5-alkynylaminocarbonylthiazol-2-yloxy)-2-propanols. The 1-alkylamino-3-(5-alkynylaminocarbonylthiazol-2-yloxy)-2-propanols can be prepared by base or acid hydrolysis of the corresponding 5-(5-alkynylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidine or derivative; or by treatment of the corresponding 3-(5-alkynylaminocarbonylthiazol-2-yloxy)-2,3-epoxypropane with the desired alkylamine.
Type:
Grant
Filed:
July 19, 1976
Date of Patent:
December 20, 1977
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Belig M. Berkoz, Brian Lewis, Stefan H. Unger
Abstract: 21-Cyclic acetals of steroids of the corticoid series are prepared from the corresponding 21-hydroxy steroids. The products have utility as anti-inflammatory agents.
Abstract: Esters of 6,11-dihydrodibenzo-[b.e.]-thiepin-11-ones of the formula: ##STR1## wherein R is hydrogen or methyl and R.sup.1 is --CH.sub.2 --CH(OH)--CH.sub.2 OH, ##STR2## where Y is either O or S, or ##STR3## where R.sup.2 and R.sup.3 are independently hydrogen, alkyl having 1 to 6 carbon atoms, phenyl or benzyl or together R.sup.2 and R.sup.3 form an alkylene bridge having 4, 5 or 6 carbon atoms, and processes for the production thereof.
Abstract: Processes and intermediates for preparing 1-alkylamino-3-(5-substitutedaminocarbonylthiazol-2-yloxy)-2-propanols and 5-(5-substitutedaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidine and 2-substituted oxazolidine derivatives thereof and intermediates therefore. The present processes, and intermediates, reduce the number of transformations necessary to produce these products as compared with the prior processes. The products are useful to treat abnormal heart conditions and/or hypertension in mammals. The intermediates are 2-alkylsulfinyl-5-substitutedaminocarbonylthiazoles and 2-alkylsulfonyl-5-substitutedaminocarbonylthiazoles.
Type:
Grant
Filed:
July 19, 1976
Date of Patent:
December 20, 1977
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Belig M. Berkoz, Brian Lewis, Joseph M. Muchowski
Abstract: 1-Alkylamino-3-(5-alkenylaminocarbonylthiazol-2-yloxy)-2-propanol; 5-(5-alkenylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidine and/or 2-substituted oxazolidine derivatives thereof, and methods of making such compounds. The compounds exhibit cardiovascular activity and are useful in the treatment of abnormal heart conditions in mammals. The compounds are also useful in the treatment of hypertension in mammals. The 5-(5-alkenylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidines and derivatives are also intermediates for the 1-alkylamino-3-(5-alkenylaminocarbonylthiazol-2-yloxy)-2-propanols. The 1-alkylamino-3-(5-alkenylaminocarbonylthiazol-2-yloxy)-2-propanols can be prepared by base or acid hydrolysis of the corresponding 5-(5-alkenylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazolidine or derivative; or by treatment of the corresponding 3-(5-alkenylaminocarbonylthiazol-2-yloxy)-2,3-epoxypropane with the desired alkylamine.
Type:
Grant
Filed:
July 19, 1976
Date of Patent:
December 20, 1977
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Belig M. Berkoz, Brian Lewis, Stefan H. Unger
Abstract: 1-Alkylamino-3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2-propanol; 5-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxymethylene-N-alkyloxazolid ine and/or 2-substituted oxazolidine derivatives thereof, and methods of making such compounds. The compounds exhibit cardiovascular activity and are useful in the treatment of abnormal heart conditions in mammals. The compounds are also useful in the treatment of hypertension in mammals. The 5-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazoli dines and derivatives are also intermediates for the 1-alkylamino-3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2-propanol s. The 1-alkylamino-3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2-propanol s can be prepared by base or acid hydrolysis of the corresponding 5-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxymethylene)-N-alkyloxazoli dine or derivative; or by treatment of the corresponding 3-(5-carbocyclicalkylaminocarbonylthiazol-2-yloxy)-2,3-epoxypropane with the desired alkylamine.
Type:
Grant
Filed:
July 19, 1976
Date of Patent:
December 20, 1977
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Brian Lewis, Stefan H. Unger, Karl G. Untch
Abstract: Novel thioesters of 6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-acetic acid, (dl) 2-(6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-yl)propionic acid and the individual (d) isomers of the latter, and processes for making the same.
Abstract: Novel prostaglandin intermediates and process for the production thereof. Compounds, and process for the production thereof, useful in the production of (dl)-[1.alpha.-hydroxy-3.beta.-(3S-tetrahydropyranyloxy-trans-1-octenyl)-4 .alpha.-tetrahydropyranyloxy-cyclopent-1.alpha.-yl] acetaldehyde hemiacetal and [1.alpha.-hydroxy-3.beta.-(3S-tetrahydropyranyloxy-trans-1-octenyl)-4.alph a.-tetrahydropyranyloxycyclopent-1.alpha.-yl] acetaldehyde hemiacetal.
Type:
Grant
Filed:
August 23, 1976
Date of Patent:
October 25, 1977
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Francisco S. Alvarez, Albert R. Van Horn
Abstract: This invention relates to a novel method for the preparation of 6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-acetic acid and the novel intermediates 3-(2-dialkylamino-2-dialkylphosphonylvinyl)-6,11-dihydrodibenzo-[b.e.]-thi epin-11-one in the preparation thereof.
Abstract: This invention relates to a novel method for the preparation of 6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-acetic acid and the novel intermediate 6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-carboxaldehyde used in the preparation thereof.
Type:
Grant
Filed:
June 18, 1976
Date of Patent:
September 27, 1977
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Anthony Prince, Otto Halpern, Jack Ackrell
Abstract: 6,11-Dihydrodibenzo-[b.e.]-thiepin-11-one-3-acetic acid is prepared from 6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-acetonitrile, a novel intermediate, by strong acid or base hydrolysis.
Abstract: This invention relates to a method of treating allergic, dermatologic and rheumatic diseases in mammals which comprises daily orally administering to said mammal in a single dose an effective amount of 6-chloro-11.beta.,17.alpha.,21-trihydroxypregna-1,4,6-triene-3,20-dione.
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: 13-Cis prostaglandin derivatives; cis-octenol ether copper.sup.(I) lithium reagents and methods of making such reagents and using the reagents to prepare the 13-cis prostaglandin derivatives. The 13-cis prostaglandin derivatives exhibit prostaglandin-like pharmacological properties and are further useful as intermediates for the corresponding prostaglandin isomers having the normal 13-trans configuration.
Type:
Grant
Filed:
December 9, 1974
Date of Patent:
September 6, 1977
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Arthur F. Kluge, Karl G. Untch, John H. Fried
Abstract: Novel 2-substituted-1,2,4-thiadiazolo-[2,3-a]-benzimidazoles of the formula ##STR1## 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: Novel racemic and antimeric prostaglandin analogs having a difluoromethylene group attached to the C-11,12 positions of the molecule, and oxygenated functions at C-9 and C-15, which may be further substituted at C-15 by a methyl group and processes for the production of such compounds. Also included are the lower alkyl esters of the carboxylic acid function and pharmaceutically acceptable salts thereof. These compounds possess prostaglandin-like activities and thus are useful in the treatment of mammals, where prostaglandins are indicated.
Abstract: Novel prostaglandin intermediates and process for the production thereof. Compounds, and process for the production thereof, useful in the production of (dl)-[1.alpha.-hydroxy-3.beta.-(3S-tetrahydropyranyloxy-trans-1-octenyl)-4 .alpha.-tetrahydropyranyloxycyclopent-1.alpha.-yl] acetaldehyde hemiacetal and [1.alpha.-hydroxy-3.beta.-(3S-tetrahydropyranyloxy-trans-1-octenyl)-4.alph a.-tetrahydropyranyloxycyclopent-1.alpha.-yl] acetaldehyde hemiacetal.
Type:
Grant
Filed:
January 15, 1975
Date of Patent:
December 21, 1976
Assignee:
Syntex (U.S.A.) Inc.
Inventors:
Francisco S. Alvarez, Albert R. Van Horn