American Cyanamid Company

Thomas H Claus

Vern G DeVries

Minu D Dutia

Jonathan D Bloom

Jo A Dolan

Middleton B Floyd, Jr

Semiramis Ayral-Kaloustian

Joseph William Epstein

Gary H Birnberg

Elwood Eugene Largis

Jo A Goidl

The invention is antiobesity/antidiabetes beta-3 agonists of the formula: ##STR1## wherein Ar, X, R.sub.2, R.sub.3, Y and n are as defined in the specification.

.beta..sub.3 -adrenergic agents, benzodioxole dicarboxylates and their

.beta..sub.3 -adrenergic agents benzodioxole dicarboxylates and their

The present invention discloses substituted 1,3-benzodioxoles which possess anti-diabetic and/or anti-hyperglycemic and/or anti-obesity properties in humans and other animals.

Substituted 5-(2-((2-aryl-2-hydroxyethyl)amino)propyl)-1,3-benzodioxoles

A process is disclosed for obtaining the R,R isomer of: ##STR1## wherein R.sub.1 and R.sub.2 may be one or more groups which may be the same or different and are selected from the group consisting of hydrogen, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, hydroxy, halogen, trifluoromethyl, carboxy, hydroxyalkyl, alkoxycarbonyl, C.sub.1 to C.sub.4 thioalkyl, sulfonyl and sulfinyl; X is a divalent radical consisting of ##STR2## wherein R' is hydrogen; R.sub.2 and R.sub.3 may be the same or different and are selected from the group consisting of hydrogen and C.sub.1 to C.sub.4 alkyl; R.sub.5 and R.sub.6 are selected from the group consisting of hydrogen, carboxy, alkoxycarbonyl, hydroxymethyl, --CH.sub.2 OCH.sub.2 COOR.sub.7 and --CH.sub.2 OCH.sub.2 CH.sub.2 OR.sub.7 where R.sub.7 is hydrogen or C.sub.1 to .sub.4 alkyl; except that R.sub.5 and R.sub.6 may not both be hydrogen; and the asterisks denote asymmetric carbon atoms; said process comprising the steps of:

Substituted 5-(2-(2-aryl-2-hydroxyethyl)-amino)propyl)-1,3-benzodioxoles

Method of increasing lean meat in edible animals

Phosphates are disclosed which stimulate the enzyme fructose-1,6-bisphosphatase and inhibit the enzyme 6-phosphofructo-1-kinase, thereby lowering glucose levels in mammals. These phosphates may thus be used to treat hyperglycemia and/or diabetes. Processes for the synthesis of the phosphates are also disclosed.

Antidiabetic phosphates

Phosphonates are disclosed which stimulate the enzyme fructose-1,6-bisphosphatase and inhibit the enzyme 6-phosphofructo-1-kinase, thereby lowering glucose levels in mammals. These phosphonates may thus be used to treat hyperglycemia and/or diabetes. Processes for the synthesis of the phosphonates are also disclosed.

Antidiabetic phosphonates

Alpha-substituted phosphonates are disclosed which stimulate the enzyme fructose-1,6-bisphosphatase and inhibit the enzyme 6-phosphofructo-1-kinase, thereby lowering glucose levels in mammals. These alpha-substituted phosphonates may thus be used to treat hyperglycemia and/or diabetes. Processes for the synthesis of the alpha-substituted phosphonates are also disclosed.

Antidiabetic alpha-substituted phosphonates

This disclosure describes pharmaceutical compositions of matter containing 5-[1-hydroxy-2-(isopropylamino)ethyl]anthranilonitrile and the method of treating diabetes therewith.

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Montvale, NJ, United States of America

Thomas H Claus