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Arylhydroxytriazenes: A New Class of Immunosuppressants

From the Pharma Research Canada, Ltd., 250 Hymus Boulevard, Pointe Claire 730, P.Q., Canada

Abstract

In a search for new immunosuppressants, it was found that some members of the arylhydroxytriazenes were active in suppressing the immune response in experimental animals. One member of this group, 3-methyl-3-hydroxy-1-(p-isopropyl-carbomoylphenyl)triazene and designated PR-H-286 BS,¹ has been studied more closely and has the following structural formula.

This compound was readily prepared by the general method of Bamberger (1); diazotization of 4-amino-N-isopropylbenzamide and subsequent coupling with N-methylhydroxylamine gave reasonable yield. Its structure was confirmed by elemental analysis as well as by infrared and nuclear magnetic resonance spectroscopy.

The immunosuppressant activity of PR-H-286 BS was first demonstrated in the Jerne plaque-forming cell (PFC) test (2). It was equally effective when given either by the intraperitoneal or oral route, suppressing the number of PFC by 96.6% and 96.4%, respectively (Table I). With this experience all further tests were done by the oral route.

Footnotes

¹ Abbreviations used in this paper: PR-H-286 BS, 3-methyl-3-hydroxyl-1-(p-isopropyl-carbomoylphenyl)triazene; PFC, plaque-forming cell; SRBC, sheep red blood cells.