A. H. Robins Company, Incorporated

Dwight A Shamblee

Young S Lo

David A Walsh

Joseph C Nolan

William J Welstead, Jr

Ibrahim M Uwaydah

Richard P Mays

David H Causey

James R Shanklin, Jr

Methods of treating chronic arthritis and osteoporosis which utilize both known and novel compounds which would fall under the general formula:

Compounds having one or more aminosulfonyloxy radicals useful as

Compounds having one or more aminosulfaonyloxy radicals useful as

Sulfamates as antiglaucoma agents

A novel process is described for preparing azetidine and 2 or 3 methyl and ethyl azetidine free bases by reacting primary arylmethylamine having suitable bulk providing substituents attached to the methyl carbon and an appropriate propane derivative having leaving groups in the one and three position in hot organic solvent containing a non-nucleophilic base and an amount of water sufficient to promote azetidine ring formation to give N-protected-azetidines and deprotecting by hydrogenolysis under acidic conditions to give an acid salt of the azetidines and thereafter flashing off vaporized azetidine from a hot, agitated strong base solution or slurry and condensing to give the liquid azetidine free bases.

Process for synthesis of azetidine and novel intermediates therefor

Novel 2-amino-3-(alkylthiobenzoyl)phenylacetic acids, esters and metal salts have the formula: ##STR1## wherein R is hydrogen or lower alkyl, R.sup.1 is hydrogen, lower alkyl or pharmaceutically acceptable metal cation, R.sup.2 is hydrogen, halogen, lower alkyl or lower alkoxy, Am is primary amino (--NH.sub.2), methylamino or dimethylamino. The compounds have anti-inflammatory activity; have effective analgesic activity, and inhibit blood platelet aggregation.

2-Amino-3-(alkylthiobenzoyl)-phenylacetic acids

Novel 2-amino-3-benzoyl-phenylacetamides are provided having the formula: ##STR1## wherein R represents hydrogen or lower alkyl, R.sup.1 and R.sup.2 represent hydrogen, lower alkyl, cycloalkyl, phenyl and phenyl substituted by lower alkyl, lower alkoxy, halogen, nitro and trifluoromethyl, and R.sup.1 and R.sup.2 when taken together with the adjacent nitrogen may form a heterocyclic residue; X represents hydrogen, lower alkyl, lower alkoxy, halogen or trifluoromethyl; Y represents hydrogen, lower alkyl, lower alkoxy, halogen, trifluoromethyl, lower alkylthio, lower alkyloxythio or lower alkyldioxythio; Am is primary amino (--NH.sub.2), methylamino or dimethylamino, and n is 1 to 3 inclusive. The compounds exhibit anti-inflammatory, antipyretic, anti-blood platelet aggregation and analgetic pharmacological activities.

Method of producing an inhibitory effect on blood platelet aggregation

Cis and trans 3-amino-4-hydroxypyrrolidines and derivatives thereof are disclosed having the formula: ##STR1## wherein R.sub.1 is hydrogen, loweralkyl or phenylcarbonyl; R.sub.2 is hydrogen, loweralkyl, lowercycloalkyl, phenyl or phenylloweralkyl; R.sub.3 is hydrogen, loweralkyl, phenylloweralkyl, phenylcarbonyl, diphenylmethyl, 5-yl-10,11-dihydro-5H-dibenzo[a,d]cycloheptene or naphthylcarbonyl; R.sub.4 is hydrogen, loweralkyl, phenylloweralkyl or lowercycloalkyl; phenyl is optionally substituted and acid addition salts thereof. The compounds have antidepressant activity and methods and pharmaceutical compositions for use thereof are disclosed.

Growing community of inventors

Richmond, VA, United States of America

Dwight A Shamblee