- NEW 2-SUBSTITUTED INDAZOLES, METHODS FOR PRODUCING SAME, PHARMACEUTICAL PREPARATIONS THAT CONTAIN SAME, AND USE OF SAME TO PRODUCE DRUGS
-
The present application relates to novel substituted indazoles, to processes for preparation thereof, to the use thereof alone or in combinations for treatment and/or prophylaxis of diseases, and to the use thereof for production of medicaments for treatm
- -
-
Paragraph 0462; 0463
(2019/03/14)
-
- 2-Thioalkyl Penems: An Efficient Synthesis of Sulopenem, a (5R,6S)-6-(1(R)-Hydroxyethyl)-2--2-penem Antibacterial
-
A practical synthesis of potent penem antibacterials, CP-70,429 (1) (sulopenam) and CP-81,054 (2), is described. (L)-Aspartic acid was utilized to generate both the (3S)- and (3R)-thiolanylthio side chains of (5R,6S)-6-(1-(R)-hydroxyethyl)-2--2-penem-3-carboxylic acids 1 and 2.This synthetic pathway provided in high yield enantiopure thioacetate intermediates 15 and 19.To accommodate the fragile side chain sulfoxide moiety of the targeted β-lactams, standard penem synthetic methodology was modified to facilitate the conversion of 15 and 19 to 1 and 2.The reactive chloroazetidinone 4b was utilized to generate key azetidinone trithiocarbonate intermediate 22 which contains the requisite penem side chain.A chemoselective oxalofluoride-based azetidinone N-acylation procedure, which avoids sulfoxide O-acylation, was required for the conversion of 22 to the penem framework.
- Volkmann, Robert A.,Kelbaugh, Paul R.,Nason, Deane M.,Jasys, V. John
-
p. 4352 - 4361
(2007/10/02)
-
- Diastereomeric 5R,6S-6-(1R-hydroxyethyl)-2-(cis-1-oxo-3-thiolanylthio)-2-penem-3-carboxylic acids
-
Diastereomeric 5R,6S-6-(1R-hydroxyethyl)-2-(1S-oxo-3R-thiolanylthio)-2-penem-3-carboxylic acid and 5R,6S-6-(1R-hydroxyethyl)-2-(1R-oxo-3S-thiolanylthio )-2-penem-3-carboxylic acid, and pharmaceutically-acceptable salts and in vivo hydrolyzable esters thereof, useful as systemic antibacterial agents; and intermediates and processes which are useful in the said synthesis of said diastereoisomers.
- -
-
-
- Process for the preparation of penems
-
An efficient, multistep process for the synthesis of 6-(1-hydroxyethyl) 2-thio-substituted penem antibiotics from 2-[4R-(triphenylmethy lthio)-3S-(1S-(dimethyl-t-butylsilyloxy)ethyl)-2-azetidon-1-yl]acetic acid esters.
- -
-
-