A. H. Robins Company, Incorporated

E.i. Dupont De Nemours and Company

The Dupont Merck Pharmaceutical Company

Other

Merck + Co., Inc.

Dupont Pharmaceuticals, Inc.

Young S Lo

William J Welstead, Jr

Dwight A Shamblee

Lucius Thomas Rossano

David A Walsh

Chandler R Taylor, Jr

Ibrahim M Uwaydah

Joseph C Nolan

Richard P Mays

Albert D Cale, Jr

Harry R Munson, Jr

David H Causey

Robert D Larsen

Anthony O King

This invention relates to novel compounds and derivatives thereof containing a trioxepane protected diol in addition to a hydrazone, hydrazine, amine, or cyclic urea moiety; methods for the preparation of said compounds; and the use of said compounds in processes to prepare human immunodeficiency virus (HIV) protease inhibitors which effectively inhibit HIV. The novel compounds provided by this invention have the formulae: ##STR1## wherein the substituents are as defined herein.

Processes and intermediates for the preparation of cyclic urea HIV

Intermediates for the preparation of cyclic urea

Method for the preparing biphenyltetrazole compounds which are angiotensin II receptor antagonists or which are useful intermediates to prepare angiotensin II receptor antagonists. An illustrative biphenyl tetrazole compound is 2-n-butyl-4-chloro-1-[(2'-(tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-im idazole-5-methanol, potassium salt.

Process for preparing biphenyltetrazole compounds

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

Method for the preparation of novel tetrazolyphenylboronic acids such as the compound 2-(2'-triphenylmethyl-2'H-tetrazol-5'-yl)phenylboronic acid.

Process for preparing tetrazolylphenylboronic acid intermediates

Compounds having one or more aminosulfaonyloxy radicals useful as

Sulfamates as antiglaucoma agents

This invention relates to an improved process for the preparation of 3-phenoxy-1-azetidinecarboxamides of Formula I which are useful ##STR1## in the treatment of epileptic seizures. Under Formula I, n is 1 to 3, X is H, halogen, trifluoromethyl, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, acetyl, or aminocarbonyl, and R is H or methyl. This process involves heating a 3-phenoxyazetidine with urea to obtain the Formula I compound. Urea is inexpensive and easily removed by washing the solid Formula I product with water.

Urea fusion process for the synthesis of

Novel tetrazolylphenylboronic acids, methods for their preparation, and their use in the syntheses of angiotensin II receptor antagonists are disclosed.

Tetrazolylphenylboronic acid intermediates for the synthesis of AII

Herein disclosed is a method of treating convulsions with a pharmaceutical composition containing a compound of the formula:

Aryl and aryloxyalkyl sulfamate esters useful as anticonvulsants

A novel process is disclosed for the preparation of 3-pyrrolidinol compounds selected from the group having the formula: ##STR1## wherein: R is selected from hydrogen, loweralkyl, loweralkenyl, cycloalkyl, cycloalkyl-loweralkyl, phenyl-loweralkyl and substituted phenyl-loweralkyl; R.sup.1, R.sup.2, and R.sup.3 are selected from hydrogen, loweralkyl, and loweralkenyl; and the optical isomers thereof. In the process, 4-amino-3-hydroxybutyronitriles are reductively cyclized with Raney nickel to produce the 3-pyrrolidinol compound.

Process for preparing 3-pyrrolidinols

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

A process for the preparation of 5-halo-2-hydroxynicotinic acids having the formula: ##STR1## wherein X is chlorine or bromine, Y and Z are selected from hydrogen, loweralkyl or loweralkyl, is described wherein a corresponding 2-hydroxynicotinic acid is halogenated with alkali-metal hypohalite in a strongly alkaline solution pH 12 and above. Certain aspects of the isolation of the product are directed to avoiding replacement of the carboxy group with halogen.

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Richmond, VA, United States of America

Young S Lo