California Polytechnic State University Foundation

The Upjohn Co.

Hewitt G Wight

Tracey G Call

Marvin L Mortensen

Martin L Mortensen

The present invention to certain immunosuppressive .omega.-(alkoxycarbonyl)alkyl m-fluorodithiocarbanilates. These compounds surprisingly and unexpectedly exhibit useful immunosuppressive effects in the treatment of tissue transplantation rejection phenomena and are useful in the symptomatic treatment of autoimmune diseases.

Immunosuppressive m-fluorodithiocarbanilates

The present invention provides certain novel .omega.-(alkoxycarbonyl)alkyl esters of dithiocarbanilic acid and certain aryl-substituted acids related thereto. These compounds are disclosed as immunoregulatory agents, useful in the treatment of organ transplant reject phenomena and autoimmune diseases such as arthritis. Additionally, there is described by the present invention the immunoregulatory use of .omega.-carboxyalkyl and .omega.-(alkoxycarbonyl)alkyl esters of dithiocarbanilic acid and certain aryl-substituted acids related thereto.

Immunosuppressive method with dithiocarbamates

Immunosuppressive dithiocarbanilates

The disclosure is directed to mono- and dithiocarbamates (hereinafter thiocarbamates) corresponding to the formula RNHCXSR'COOR' wherein R is paraphenylazophenyl or metafluorophenyl, X is oxygen when R is paraphenylazophenyl and X is sulfur when R is metafluorophenyl, R' is an alkylene radical having generally from 1 to about 5 carbon atoms and R' is hydrogen or an alkyl radical having generally from 1 to about 10 carbon atoms. The thiocarbamates, in acid form, can be prepared by blocking the carboxyl group of a mercaptoalkanoic acid with a carboxyl blocking agent; interacting the carboxyl blocked, mercaptoalkanoic acid with paraphenylazophenyl isocyanate or metafluorophenyl isothiocyanate to produce a thiocarbamate reaction product; and treating the thiocarbamate reaction product to remove the carboxyl blocking agent and to obtain the product in carboxylic acid form. The thiocarbamates, in ester form, can be prepared by interacting an alkyl mercaptoalkanoate with paraphenylazophenyl isocyanate or metafluorophenyl isothiocyanate. The thiocarbamates possess the unique property of being able to modify and enhance the strength of biological membranes.

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San Luis Obispo, CA, United States of America

Hewitt G Wight