3-methylenespiro (benzofuranpiperidines)
AssigneeHoechst-Roussel Pharmaceuticals Inc.
InventorRaymond W. Kosley, Jr.
Life of this patent
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Abstract
Novel 3-methylenespiro[benzofuran-2(3H),4'-piperidines], intermediates and processes for the preparation thereof and methods for reducing blood pressure utilizing the compounds and compositions thereof are disclosed.
Claims19
A compound of the formula ##STR43## wherein R is hydrogen, loweralkyl of 1 to 6 carbon atoms, aralkyl, loweralkoxyloweralkyl having 1 to 6 carbon atoms in the alkoxy and alkyl groups, benzyloxyloweralkyl having 1 to 6 carbon atoms in the alkyl group, a group of the formula ##STR44## wherein R.sup.1 is aryl or loweralkyl of 1 to 6 carbon atoms, a group of the formula ##STR45## wherein R.sup.2 is hydrogen or loweralkyl of 1 to 6 carbon atoms, a group of the formula ##STR46## wherein R.sup.3 is hydrogen or loweralkyl of 1 to 6 carbon atoms, V is hydrogen or halogen and n is 2, 3 or 4, a group of the formula ##STR47## wherein n is 2 or 3, a group of the formula ##STR48## wherein n is 2 or 3, a group of the formula ##STR49## wherein Z is hydrogen, halogen, loweralkyl of 1 to 6 carbon atoms, loweralkoxy of 1 to 6 carbon atoms, trifluoromethyl or hydroxy and n is 1, 2, 3, or 4 or a group of the formula ##STR50## wherein n is 2, 3 or 4;
- X is hydrogen, halogen, loweralkyl of 1 to 6 carbon atoms, loweralkoxy of 1 to 6 carbon atoms, hydroxy or trifluoromethyl, an optical antipode thereof or a pharmaceutically acceptable acid addition salt thereof.
A method of preparing a compound of formula ##STR58## wherein R is a group of the formula ##STR59## wherein R.sup.1 is loweralkyl of 1 to 6 carbon atoms or phenyl or a group of the formula ##STR60## wherein R.sup.2 is hydrogen or loweralkyl of 1 to 6 carbon atoms;
- and X is hydrogen, halogen, loweralkyl of 1 to 6 carbon atoms, loweralkoxy of 1 to 6 carbon atoms, hydroxy or trifluoromethyl, which comprises contacting a compound of the formula ##STR61## wherein R and X are as above with an alkali metal nitrite in the presence of an acid and a hydrogen donor.
Dependencies are inferred from the claim text.