US RE40,033 E1 | ||
Process for preparing 2-methyl-thieno-benzodiazepine | ||
Jiban Kumar Chakrabarti, deceased, late of Hampshire (United Kingdom), by Reba Chakrabarti, legal representative; Terrence Michael Hotten, Hampshire (United Kingdom); and David Edward Tupper, Hampshire (United Kingdom) | ||
Assigned to Eli Lilly and Company, Indianapolis, Ind. (US) | ||
Filed on Dec. 18, 2001, as Appl. No. 10/23,132. | ||
Application 09/122294 is a division of application No. 08/748292, filed on Nov. 13, 1996, granted, now 5,817,655. | ||
Application 08/748292 is a continuation in part of application No. 08/387997, filed on Feb. 13, 1995, granted, now 5,627,178. | ||
Application 08/387997 is a continuation in part of application No. 08/044844, filed on Apr. 08, 1993, abandoned. | ||
Application 08/044844 is a continuation in part of application No. 07/890348, filed on May 22, 1992, granted, now 5,229,382. | ||
Application 07/890348 is a continuation of application No. 07/690143, filed on Apr. 23, 1991, abandoned. | ||
Application 10/023132 is a reissue of application No. 09/122294, filed on Jul. 24, 1998, now 6,008,216, filed on Dec. 28, 1999. | ||
Int. Cl. A01N 43/62 (2006.01); C07D 243/10 (2006.01) |
U.S. Cl. 514—220 [540/557] | 3 Claims |
1. A method of preparing 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]-benzodiazepine comprising the following
steps:
A) preparing 2-amino-5-methylthiophene-3-carbonitrile by mixing sulfur,
B) preparing 2-(2-nitroanilino)-5-methylthiophene-3-carbonitrile from the reaction product of step (A) by reaction with a
slurry of sodium hydride dispersed in oil in tetrahydrofuran and
C) preparing 4-amino-2-methyl-10H-
D) preparing 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine by refluxing the reaction product of
step (C) with a mixture of N-methylpiperazine, dimethylsulphoxide and toluene.
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