Merck + Co., Inc.

Merck Gmbh

Thomas N Salzmann

Frank P DiNinno

Ronald W Ratcliffe

Burton G Christensen

Mark L Greenlee

Gary H Rasmusson

James V Heck

Nathan G Steinberg

David A Muthard

Eugene D Thorsett

Ichiro Shinkai

David H Shih

Lelia M Fuentes

Robert R Wilkening

Ravindra N Guthikonda

William J Leanza

Kothandaraman Shankaran

Michael J Szymonifka

F Aileen Bouffard

Compounds of the formula: ##STR1## where R is hydrogen, hydroxyl, alkyl or acyl, R' and R' together are oxo, hydroxyimino or alkoxyimino, and R' and R' independently are hydrogen, hydroxyl, acyloxy, or amino substituted by any of hydrogen, alkylcarbonyl, arylcarbonyl, aralkylcarbonyl, alkoxycarbonyl, aralkoxycarbonyl, alkylsulfonyl or arylsulfonyl, and n is 0 or 1, and the pharmaceutically acceptable salts thereof. The compounds are macrolide antibiotics and are also useful as intermediates to the synthesis of other macrolide antibiotics. Pharmaceutical compositions and methods of their use are also provided for.

Homoerythromycin A derivatives modified at the 4'-and 8A-positions

New antibacterial 6-amido-1-methyl-2-(substituted-thio)-carbapenems and process for their synthesis involving new azetidinone intermediates.

6-amido-1-methyl-2-(substituted-thio)carbapenems

Carbapenems having the formula: ##STR1## are useful antibacterial agents.

2-(heterocyclylheteroaryliumalkyl) phenyl carbapenem antibacterial agents

Carbapenems of the formula: ##STR1## are useful intermediates to antibacterial agents.

2-biphenyl-carbapenems

(2-substituted phenyl) carbapenems

Carbapenems having the formula: ##STR1## where X is O or S(O).sub.0-2 ; are useful antibacterial agents, especially with respect to activity against methicillin resistant Staphylococcus aureus (MRSA).

2-(substituted-dibenzofuranyl and dibenzothienyl) carbapenem

Carbapenems of the formula ##STR1## are useful intermediates to antibacterial agents.

2-biphenyl carbapenem intermediates

Carbapenems of the formula ##STR1## are useful as intermediates to antibacterial agents.

2-phenanthrenyl carbapenem intermediates

New antibacterial spirocyclic 6-amido carbapenems of the structural formulas: ##STR1## wherein R.sup.1 is hydrogen, C.sub.1-8 substituted or unsubstituted alkyl, or C.sub.6-10 substituted or unsubstituted aryl; R.sup.5 is hydrogen or a protecting group for alcohol; R.sup.6 is hydrogen or a protecting group for amido nitrogen; R.sup.7 is hydrogen or a protecting group for amido nitrogen; and R.sup.8 is hydroxy, hydrogen, C.sub.1-8 substituted or unsubstituted thioalkyl, C.sub.6-10 substituted or unsubstituted thioaryl, 5 or 6 membered, substituted or unsubstituted thioheteroaryl; and a process for their synthesis through novel spirocyclic 4-amido azetidinones are disclosed.

Spirocyclic 6-amido-carbapenems and azetidinones

2-biphenyl-carbapenems intermediates

2-phenanthrenyl-carbapenems

Selected 17.beta.-Polyaroyl-4-aza-5.alpha.-androst-1-en-3-ones as steroidal reductase inhibitors of the formula: ##STR1## wherein R is selected from hydrogen, methyl and ethyl

Selected 17 .beta.-polyaroyl-4-aza-5 .alpha.-androst-1-en-3-ones as

Carbapenem intermediates having the formula: ##STR1## where Z is; ##STR2## M is a removable protecting group for carboxy and P' is a removable protecting group for hydroxy are useful intermediates for preparing antibacterial agents, especially with respect to activity against methicillin resistant Staphylococcus aureus (MRSA).

Intermediates for preparing 2-(substituted-dibenzofuranyl and

Specific 17.beta.-thiobenzoyl-4-aza-5.alpha.-androst-1-en-3-ones as antiandrogenic agents of the formula: ##STR1## wherein R is selected from hydrogen, methyl and ethyl and

Specific 17.beta.-thiobenzoyl-4-aza-5.alpha.-androst-1-en-3-ones as

New antibacterial 6-amido-1-methylcarbapenems and process for their synthesis involving new azetidinone intermediates.

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North Plainfield, NJ, United States of America

Thomas N Salzmann