Abstract: A process for irreversible regio- and stereoselective enzyme catalyzed acylation of alcohols using enol esters as acylating reagents is disclosed. The present invention permits the selective modification of hydroxyl group(s) of chiral and meso alcohols, including sugars, organometallics, and glycosides. The enol freed upon transesterification rapidly tautomerizes to the corresponding volatile aldehyde or ketone thereby preventing the reverse reaction from occurring.
Type:
Grant
Filed:
August 24, 1989
Date of Patent:
April 21, 1992
Assignee:
G. D. Searle & Co.
Inventors:
Chi-Huey Wong, Yi-Fong Wang, William J. Hennen, Kevin A. Babiak, John H. Dygos, John S. Ng
Abstract: This invention encompasses a process for preparing higher order cuprate complexes which contain a carbanion for the formation of carbon to carbon bonds in reactions such as 1,4-conjugate addition. The complex is formed by reacting a first cuprate cmoplex with a stannane such that the carbanion to be used to form carbon to carbon bonds is transferred from the stannane to the first cuprate complex to form a different higher order cuprate complex. This process permits the in situ preparation of a higher order cuprate complex having the carbanion desired to be used in a synthetic reaction. Higher order cuprate complexes prepared by this process are particularly useful for the efficient preparation of pharmacologically active prostaglandins.
Abstract: This invention related to leukotriene B.sub.4 antagonists having the structure ##STR1## and the pharmaceutically acceptable addition salts thereof; wherein R.sup.1 is lower alkyl having 1-10 carbon atoms; or lower alkenyl or alkynyl having 2-10 carbon atoms; or lower alkadienyl having 3-10 carbon atoms; or lower alkadienyl or alkenynyl having 4-10 carbon atoms;wherein R.sup.2 and R.sup.3 are the same or different and represent hydrogen or lower alkyl having 1-6 carbon atoms;wherein X is CH.dbd.CH, S, or O;wherein Y is CH.dbd.CH or C.tbd.C;wherein Z is OR.sup.4 or NR.sup.5 R.sup.6, and wherein R.sup.4 represents H, lower alkyl having 1-6 carbon atoms, or a pharmaceutically acceptable cation, and wherein R.sup.5 and R.sup.6 act independently and represent H or lower alkyl having 1-6 carbon atoms, or R.sup.5 and R.sup.
Type:
Grant
Filed:
June 3, 1988
Date of Patent:
January 23, 1990
Assignee:
C. D. Searle & Co.
Inventors:
Stevan W. Djuric, Richard A. Haack, Julie M. Miyashiro
Abstract: This invention encompasses compounds of Formula 1 and the pharmaceutically acceptable salts thereof. ##STR1## wherein R.sup.1 represents alkyl having 2-6 carbon atoms;R.sup.2 represents methyl or ethyl;R.sup.3 represents alkyl having 1 to 5 carbon atoms;W represents (CH.sub.2).sub.x where x is 2 to 7, alkylene having 2 to 7 carbon atoms, alkenylene having 3 to 7 carbon atoms, alkynylene having 3 to 7 carbon atoms, or cyclopentyl;R.sup.4 represents hydrogen, alkyl having 2-5 carbon atoms, alkenyl having 2 to 5 carbon atoms, or alkynyl having 2 to 5 carbon atoms;Q represents oxygen or CH.sub.2 ;B represents CH.sub.2, C.dbd.O or CH--OH;R.sup.5 represents hydrogen, alkyl having 1 to 6 carbon atoms, or R.sup.5 and R.sup.6 together optionally represent a carbon to carbon bond; orR.sup.5 represents alkanoyl having 2 to 4 carbon atoms, carboxy, alkoxycarbonyl, or (CH.sub.2)y--CO.sub.2 R.sup.8 wherein y is 0 to 4 and R.sup.8 is hydrogen or alkyl having 1 to 6 carbon atoms; andA represents --Z--CO.sub.2 R.sup.
Type:
Grant
Filed:
May 12, 1988
Date of Patent:
December 26, 1989
Assignee:
G. D. Searle & Co.
Inventors:
Stevan W. Djuric, Robert L. Shone, Stella S. T. Yu
Abstract: A method and assembly provided for the detection and determination of at least one ligand in a sample suspected of containing the ligand. The method includes providing in a hand-held assembly having a first chamber and a second chamber separated by a separation means which permits the passage therethrough of materials of a relatively small size while preventing the passage therethrough of materials of a relatively larger size; a suspension in the first chamber of an admixture of a binding partner for the ligand and a labeled component. The labeled component is selected from the group consisting of binding partner, compound which can bind to the binding partner, compound which can bind to the reaction product of the ligand and binding partner, and compound which can bind to the ligand. The sample suspected of containing the ligand is introduced to the first chamber.