A. H. Robins Company, Incorporated

Philip Morris Inc.

Lina C Teng

David A Walsh

James R Shanklin, Jr

William L Smith

Reevis S Alphin

Lennox B Turnbull

George J Wright

Stephen C Bearekman

A method of treating cardiac dysfunction, the effects of histamine, and gastric secretion excesses with aryl(alkyl and alkylene)-N-[(phenoxy and phenythio)alkyl]aminoheterocyclics corresponding to the formula: ##STR1## wherein Ar is phenyl or substituted phenyl; R is phenyl, substituted phenyl, pyridinyl or cycloalkyl; A is hydrogen, hydroxy, cyano, amido and amino; Q is --CH.sub.2 --, --CH--, or --CHOH--; d and n are zero or one and the dotted lines form double bonds consistent with the valence of carbon; p is zero, one or two; m is one to six inclusive; B is oxygen, nitrogen, sulfur, sulfinyl or sulfonyl; z is zero or one; l is zero or one; W is hydrogen, loweralkyl, halo, nitro, loweralkoxy or hydroxy; X is hydrogen, loweralkyl, halogen, loweralkoxy or hydroxy; Y is --CH(OH)CH.sub.2 OH, --CH(OH)C(O)OH, --C(O)C(O)OH, --C(O)CH.sub.2 OH,--C(O)C(O)OCH.sub.3, --C(O)C(O)OC.sub.2 H.sub.5, --CH.sub.2 C(O)OC.sub.2 H.sub.5, --CH(OH)C(O)OCH.sub.3, --CH(OH)C(O)OC.sub.2 H.sub.5 or --C(O)CH.sub.2 OC(O)CH.sub.3 ; and the pharmaceutically acceptable salts thereof; in addition to the above methods of treatment, compounds wherein (B).sub.z is oxygen are useful in a method of treating Gell and Coombs type 1 allergic responses in mammals.

Aryl(alkyland alkylene)-N-((phenoxy and phenylthio)alkyl)

A method of controlling emesis caused by anticancer drugs with 2-alkoxy-N-(1-azabicyclo[2.2.2]oct-3-yl) benzamide-N-oxides having the formula: ##STR1## wherein R.sub.1 is loweralkyl, and R.sub.2 is selected from the group consisting of hydrogen, halo, 4,5-benzo, methylsulfonyl, loweralkoxy or Am and n is 1 or 2, and the pharmaceutically acceptable acid addition salts thereof is disclosed.

Method of using

3-Phenoxy-1-azetidinecarboxamides having the formula ##STR1## wherein R.sup.1 is selected from the group consisting of hydrogen, fluoro, loweralkyl, loweralkoxy, trifluoromethyl, acetyl or aminocarbonyl having prolonged anticonvulsant activity are disclosed.

3-Phenoxy-1-azetidinecarboxamides

N-Formyl and N-hydroxymethyl-3-phenoxy-1-azetidinecarboxamides having the formula: ##STR1## wherein R is selected from formyl and hydroxymethyl and R.sup.1 is selected from hydrogen, fluoro, loweralkyl, loweralkoxy, trifluoromethyl, acetyl, N-formylcarboxamido or N-hydroxymethylcarboxamido having antidepressant activity are disclosed.

N-Formyl and N-hydroxymethyl-3-phenoxy-1-azetidinecarboxamides

A smoking composition is provided which comprises a smoking material and, as a source of flavor or aroma for the smoke thereof, certain aromatic beta-hydroxy compounds. Compounds which may be employed as a source of flavor or aroma include beta-hydroxy esters formed by condensing, using a Reformatsky-type reaction, an alkyl alpha-bromoisobutyrate or homolog thereof with an aromatic aldehyde such as benzaldehyde, anisaldehyde or piperonal. Other compounds which may be employed are the acids and/or metal salts which are formed by hydrolysis of such beta-hydroxy esters. Novel compositions of matter provided by the present invention include: the compound ethyl 2,2-dimethyl-3-hydroxy-3-(3',4'-methylenedioxyphenyl)-propionate, the compound n-amyl 2,2-dimethyl-3-hydroxy-3-phenylpropionate, the compound methyl 2,2-dimethyl-3-hydroxy-3-phenylpropionate, the compound 2,2-dimethyl-3-hydroxy-3-(3',4'-methylenedioxyphenyl) propionic acid, the compound ethyl 2,2-dimethyl-3-hydroxy-3-(p-methylphenyl)propionate, and the compound ethyl 2,2-dimethyl-3-hydroxy-5-phenyl-trans-4-pentenoate. The invention enables the incorporation in smoking materials, and particularly in tobacco, of compounds which will release flavors or aromas which compounds can be maintained and preserved during subsequent processing and storage of the tobacco.

Smoking composition

A smoking composition is provided which comprises a smoking material and, as a source of flavor or aroma for the smoke thereof, certain aromatic beta-hydroxy compounds. Compounds which may be employed as a source of flavor or aroma include beta-hydroxy esters formed by condensing, using a Reformatsky-type reaction, an alkyl alpha-bromoisobutyrate or homolog thereof with an aromatic aldehyde such as benzaldehyde, anisaldehyde or piperonal. Other compounds which may be employed are the acids and/or metal salts which are formed by hydrolysis of such beta-hydroxy esters. Novel compositions of matter provided by the present invention include: the compound ethyl 2,2-dimethyl-3-hydroxy-3-(3',4'-methylenedioxyphenyl)-propionate, the compound n-amyl 2,2-dimethyl-3-hydroxy-3-phenylpropionate, the compound methyl 2,2-dimethyl-3-hydroxy-3-phenylpropionate, the compound 2,2-dimethyl-3-hydroxy-3-(3',4'-methylenedioxy phenyl) propionic acid, the compound ethyl 2,2-dimethyl-3-hydroxy-3-(p-methylphenyl)propionate, and the compound ethyl 2,2-dimethyl-3-hydroxy-5-phenyl-trans-4-pentenoate. The invention enables the incorporation in smoking materials, and particularly in tobacco, of compounds which will release flavors or aromas which compounds can be maintained and preserved during subsequent processing and storage of the tobacco.

Smoking composition and compounds therefor

A smoking composition is provided which comprises a smoking material and, as a source of flavor or aroma for the smoke thereof, certain aromatic beta-hydroxy compounds. Compounds which may be employed as a source of flavor or aroma include beta-hydroxy esters formed by condensing, using a Reformatsky-type reaction, an alkyl alpha-bromo-isobutyrate or homolog thereof with an aromatic aldehyde such as benzaldehyde, anisaldehyde or piperonal. Other compounds which may be employed are the acids and/or metal salts which are formed by hydrolysis of such beta-hydroxy esters. Novel compositions of matter provided by the present invention include: the compound ethyl 2,2-dimethyl-3-hydroxy-3-(3',4'-methylenedioxyphenyl)-propionate, the compound n-amyl 2,2-dimethyl-3-hydroxy-3-phenylpropionate, the compound methyl 2,2-dimethyl-3-hydroxy-3-phenylpropionate, the compound 2,2-dimethyl-3-hydroxy-3-(3',4'-methylenedioxy phenyl) propionic acid, the compound ethyl 2,2-dimethyl-3-hydroxy-3-(p-methylphenyl)propionate, and the compound ethyl 2,2-dimethyl-3-hydroxy-5-phenyl-trans-4-pentenoate. The invention enables the incorporation in smoking materials, and particularly in tobacco, of compounds which will release flavors or aromas which compounds can be maintained and preserved during subsequent processing and storage of the tobacco.

Growing community of inventors

Richmond, VA, United States of America

Lina C Teng