Abbott Laboratories Corporation

Other

Greenwich Pharmaceuticals Incorporated

501 Greenwich Pharmaceuticals Incorporated

Albert V Thomas

Sudershan K Arora

Bruce Ronsen

Ramiya H Premchandran

Alexandra E Graham

Roy L Whistler

Sanjay R Chemburkar

David A Riley

Juliette K Busse

Robert F Keyes

Hemant H Patel

Hemantkumar H Patel

Shyamal I Parekh

Anne H Kemp

David P Sawick

Michael John Dipierro

John E Dete

Joseph M Roman

Rachel R Yang

The claimed invention relates to a novel process of preparing N-demethyl-N-alkyl-4'-deoxy erythromycin A and B. The process comprises protecting the 2'-hydroxy or the 2'- and 11-hydroxy of a N-demethyl-4'-deoxy erythromycin derivative having the formula: ##STR1## where R.sub.b is H or OH, with a silyl protecting group and alkylating the N-position of the desosamine sugar.

Process for preparing N-demethyl-N-alkyl erythromycin derivatives

A process for the preparation of 4'-deoxyerythromycins, having the formula: ##STR1## wherein R is H or OH, R.sup.1 is H or loweralkyl, and R.sup.2 is H or CH.sub.3 by treatment of the starting material, 2'-O-acetyl-4'-imidazolylthiocarbamoyl-erythromycin, with a hypophosphite reagent, in a water-miscible protic solvent optionally comprising a phase transfer agent. In a preferred embodiment, the water-miscible solvent is an alcohol and the starting material is reacted with sodium hypophosphite, ACVA and tetra-n-butylammonium hydroxide.

Hypophosphite deoxygenation reactions in the synthesis of erythromycin

A process for the preparation of N-demethyl-4'-deoxy-erythromycins A and B, having the formula: ##STR1## wherein R.sup.a is H or OH, by stepwise addition of iodine and base to the N-dimethyl-4'-deoxyerythromycin, preferably, accompanied by sparging with an inert gas.

Process for preparation of N-demethyl-4'-deoxy-erthromycins A and B

A process for the preparation of 4'-deoxyerythromycins, having the formula: ##STR1## wherein R is H or OH, and R.sup.1 is H or loweralkyl by treatment of the 2'-O-acetyl-4'-imidazolylthionocarbonyl-erythromycin starting material with the radical initiator 4,4'-azobis-(4-cyanovaleric acid), H.sub.3 PO.sub.2 and an organic base in a water-miscible solvent and optionally eliminating the 2'-O-acetyl group. In a preferred embodiment, the water-miscible solvent is an alcohol and the deoxygenation and deacetylation is carried out in one step.

Process for preparation of 4'-deoxyerythromycins A and B

The present invention provides a process for the preparation of a compound of formula ##STR1## wherein R is a straight or branched alkyl group of from one to twelve carbon atoms; M represents hydrogen or a pharmaceutically acceptable cation; and A is selected from optionally substituted carbocyclic phenyl.

Process for the preparation of arylalkynyl-N-hydroxyurea derivatives

Derivatives of simple monosaccharides which exhibit anti-proliferative and/or anti-inflammatory activity and are useful for treating mammals having inflammatory disorders and/or autoimmune disorders. This invention also encompasses pharmaceutical compositions containing these compounds and methods of treating inflammatory and/or autoimmune disorders.

Monosaccharides having anti-proliferation and anti-inflammatory

Derivatives of 1,2-O-isopropylidene-.alpha.,D-glucofuranose and intermediates for preparing these derivatives are described. These derivatives are useful for treating animals and mammals with inflammatory and/or autoimmune disorders such as autoimmune deficiency syndrome, psoriasis, atopic dermatitus, rheumatoid arthritis, osteoarthritis, scleroderma and systemic lupus erythematosus.

3,5,6-substituted derivatives of

Derivatives of -.alpha.,D-glucofuranose .alpha.,D-allanfuranose and intermediates for preparing these derivatives are described. These derivatives are useful for treating animals and mammals with inflammatory and/or autoimmune disorders such as psoriasis, atopic dermatitus, rheumatoid arthritis, osterarthritis, scleroderma and systemic lupus erythematosus.

Derivatives of .alpha.,D-glucofuranose or .alpha.,D-allofuranose and

An improvement in a boring bar assembly is disclosed. The improvement relates to a lateral bar assembly in combination with the adjustable boring bar assembly of U.S. Pat. No. 2,838,316 issued to Albert Thomas, a co-inventor of the present invention. The improvement includes a lateral bar to which a major portion of the shank member of the boring bar assembly is removably fixed. The lateral bar has a plurality of longitudinally spaced threaded receptacles into which an end of the shank may be screwed. The shank may be selectively screwed into the lateral bar to thereby change the diameter of the boring bar assembly. The lateral bar may be varied in overall length with the number of receptacles likewise varied to thus vary the magnitude of the ranges of diameters of operation of the boring bar assembly.

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Vernon Hills, IL, United States of America

Albert V Thomas