1461225 Pyrrolobenzodiazepines AMERICAN CYANAMID CO 7 April 1975 [26 April 1974] 14188/75 Heading C2C 1,2,3,11a - Tetrahydro - 10 - methyl - 5H- pyrrolo[2,1-c][1,4]benzodiazepin - 5,11(10H)- dione is prepared by (a) cyclizing 1-(N-methylanthraniloyl)proline, N-(2-pyrrolidylcarbonyl)- N - methylanthranilic acid or an ester of either acid, (b) heating N-methylisatoic anhydride and proline or (c) methylation. An optically active starting material may be used. 1 - (N - methylanthraniloyl)proline and its esters are prepared by reacting N-methylisatoic anhydride and proline or an ester thereof, and ethyl N - (2 - pyrrolidylcarbonyl - N - methylanthranilate is prepared by converting N- benzylproline to the acid chloride and condensing with ethyl N-methylanthranilate, followed by debenzylation. The dextrorotatory and racemic products are anxiolytics, and may be administered in the form of pharmaceutical preparations containing them in association with a carrier.
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