GB1002860A - Azathioxanthene derivatives - Google Patents

Abstract

The invention comprises compounds of general formula <FORM:1002860/C2/1> wherein A represents a straight or branchedchain alkylene group containing 2 to 6 carbon atoms and such that the carbon atom linked to the azathioxanthene nucleus is primary or secondary, and Z represents a dialkylamino group in which each alkyl group contains not more than 6 carbon atoms; non-toxic acid addition and quaternary ammonium salts thereof; and their preparation by (1) reacting a 10-(alkali metal)-derivative of 1-azathioxanthene with a compound X-A-Z where X is the acid residue of a reactive ester, (2) reducing by known methods a 10 - hydroxy - 10 - (AZ) - azathioxanthene, (3) hydrogenating by known methods a 10-(BZ)-azathioxanthene where B is an alkanylidene radical corresponding to A. Separation of optical isomers is mentioned. Other processes outlined are (1) reaction of a 10-(AX)-azathioxanthene with a compound HZ, (2) reduction of a corresponding 10-(dialkylamido-alkylene)-azathioxanthene, and (3) reaction of 10-halo-azathioxanthenes with Grignard reagents. 10 - Hydroxy - 10 - (AZ) - azathioxanthenes are prepared by reaction of 10-oxo-azathioxanthene with organo-metallic, e.g. Grignard, derivatives containing -AZ; dehydration yields 10-(BZ)-azathioxanthenes. Salts of starting materials are obtainable. 10 - (Dialkylamido - alkylene) - azathioxenthenes may be prepared from corresponding acid chlorides and compounds HZ. 10 - Oxo - azathioxanthene is prepared from 2-carboxy - 3 - phenylthiopyridine in tetrahydrofuran, and yields the azathioxanthene on reduction with hydrazine. Pharmaceutical compositions comprise compounds I and salts of the invention with pharmaceutical carriers or coatings. Oral (tablets, pills, powders, granules, capsules, emulsions, solutions, suspensions, syrups, elixirs), parenteral (solutions, suspensions, emulsions) and rectal (suppositories) administration is mentioned. They have antihistaminic, spasmolytic, antitursive and analgesic effects.