Philip Morris Inc.

Philip Morris Products Inc.

Henry V Secor

Jeffrey I Seeman

Edward B Sanders

William B Edwards, Iii

Thomas S Osdene

Yoram Houminer

Charles R Howe

Robert N Ferguson

Norman H Cromwell

This invention provides novel organic acids which exhibit utility as liquid ion exchanges suitable for use in an invention solvent extraction process. Illustrative of an invention organic acid is a compound corresponding to the formula: ##STR1## where each of R.sub.1 and R.sub.2 is a C.sub.3 -C.sub.16 branched alkyl group.

Extraction process using a novel organic acid as a liquid ion exchanger

This invention provides a class of nicotine analogs which as therapeutic agents exhibit tranquilizing effects in mammals. Illustrative of an invention nicotine analog is 3-[N-methyl-N-(3-aminopropyl)]aminomethylpyridine ##STR1## the nicotine analogs can exist in the form of acid addition salts.

Nicotine analogs

This invention privdes novel heteroaromatic compounds, and smoking compositions which contain an invention heteroaromatic compound as a flavorant-release additive as illustrated by the following additive structure: ##STR1## Under typical cigarette smoking conditions, 2-isopropylpyrazine and acetophenone are released as pyrolysis products, and enhance the flavor and aroma of the mainstream and sidestream smoke.

Smoking compositions containing a heteroaromatic flavorant-release

This invention provides a novel class of nicotine analogs which as therapeutic agents exhibit tranquilizing effects in mammals. Illustrative of invention nicotine analogs are 1-(3-dimethylaminopropyl)-2-(3-pyridyl)pyrrolidine: ##STR1## and (R,S)-6-(N,N-dimethyl-3-aminopropyl)nicotine: ##STR2## The nicotine analogs can exist in the form of acid addition salts.

The invention relates to 2-alkyl nicotinoids and improved methods for producing them.

Process for preparing 2-alkyl nicotinoids

A process for the production of .gamma.-amino alcohols from .beta.-dicarbonyl compounds is disclosed. The dicarbonyls are reacted with alkoxyamines and the resultant alkoximino compounds reduced to yield .gamma.-amino alcohols. Also described are novel substituted .gamma.-amino alcohols.

Method of producing .gamma.-amino alcohols

Novel azetidine, and particularly 2-pyridyl-azetidine, compounds are disclosed. These compounds are produced from amino-esters by a sequence comprising conversion to the sulfonamide, reduction of the ester to the alcohol, sulfonation of the resultant alcohol and cylization to the N-sulfonylazetidine. This azetidine compound may then be transformed, as desired, to various N-derivatives by substitution of hydrogen or other univalent organic groups on the secondary amine of the azetidine ring.

Azetidine compounds and process for production

Novel azetidine, and particularly 3-pyridyl-azetidine, compounds are disclosed. These compounds are produced from .gamma.-amino alcohols by a sequence comprising disulfonation to produce the sulfonamido-alkylsulfonate and then cyclization to the N-sulfonylazetidine. These azetidine compounds may then be transformed, as desired, to various N-derivatives by substitution of hydrogen or other univalent organic groups on the secondary amine of the azetidine ring.

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Midlothian, VA, United States of America

Henry V Secor