Robert J Morin

US Patent:

40575403, Nov 8, 1977

Filed:

Mar 17, 1976

Appl. No.:

5/667825

Inventors:

Ronald G. Micetich - Edmonton, CA
Robert B. Morin - Warren NJ
Kenneth E. Wilson - Edmonton, CA

Assignee:

Connlab Holdings Limited - Ontario

International Classification:

C07D20508
C07D51304
C07D41712

US Classification:

260239A

Abstract:

The invention relates to novel azetidinones of the general formula: ##STR1## wherein R stands for lower alkyl, phenyl, phenyloxyloweralkyl, phenylloweralkyl, 2-thiophenemethyl, 5-tetrazolylmethyl, R. sup. 3 O--and R. sup. 3 S--, wherein R. sup. 3 stands for lower alkyl, phenyl or phenylloweralkyl; R. sup. 1 is hydrogen or a cleavable radical selected from lower alkyl; loweralkoxymethyl, 2,2,2-trichloroethyl, benzyl, p-halobenzyl, p-nitrobenzyl and p-methoxybenzyl, benzhydryl and trimethylsilyl; R. sup. 2 is hydrogen or methoxy; X is SCl, Sbr or --OH in which case the C. sub. 3 -sidechain is better represented as the amide RCONH-- group; Y is chloro or bromo; and ##STR2## may also be taken as phthalimido. These novel compounds possess antibacterial activity and are useful intermediates for the synthesis of modified penicillins and the analogues of penicillins.

US Patent:

40910261, May 23, 1978

Filed:

Oct 15, 1975

Appl. No.:

5/622627

Inventors:

Ronald G. Micetich - Edmonton, CA
Clinton G. Chin - Edmonton, CA
Robert B. Morin - Warren NJ

Assignee:

Connlab Holdings Limited

International Classification:

C07D51304

US Classification:

2603067C

Abstract:

An improved process for preparing 4-thia-2,6-diazabicyclo[3,2,0]hept-2-ene-7-ones such as methyl 3-phenoxy-4-thia-2,6-diazabicyclo[3,2,0]hept-2-ene-7-one-6-isopropenylacet ate which comprises extruding sulfur from dithiazeneazetidinones such as methyl 3-phenoxymethyl-4,5-dithia-2,7-diazabicyclo[4,2,0]-oct-2-ene-8-one-7-isopr openylacetate. The compounds obtained are useful intermediates in the preparation of certain 3-cephems.