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Substituted 6-(piperazinyl)-10H-pyrido[3,2-b]thieno[3,4-e][1,4]-diazepines
| Details |
Inventors: Safir, Sidney Robert; Hofmann, Corris Mabelle;
Assignee: American Cyanamid Company (Stamford, CT)
Primary Examiner: Coughlan, Jr.; Paul M.
Assistant Examiner: Tovar; Jose
Attorney, Agent or Firm: Johnson; Norton S.
Various substituted 6-(piperazinyl)10H-pyrido[3,2-b]thieno[3,4-e][1,4]-diazepines which have demonstrated anti-psychotic activity are disclosed. |
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DETAILED DESCRIPTION We claim: 1.
The compound 6-(4-methyl-1-piperazinyl)-10H-pyrido[3,2-b]thieno[3,4-e][1,4]-diazepine.
Description:
Description of the Prior Art U.
S.
Pat.
No.
3,953,430, Safir, discloses lactams of the following formula: ##STR1## More specifically, the compounds where Z is N and R, and R.
sub.
1 and R.
sub.
2 are H are the starting materials for the preparation of the compounds of the present invention.
SUMMARY OF THE INVENTION This application discloses novel compounds of the formula: ##STR2## wherein R is selected from the group consisting of hydrogen, lower alkyl and hydroxy lower alkyl; R.
sub.
1 is selected from the group consisting of hydrogen and lower alkyl, and pharmaceutically acceptable acid addition salts thereof.
This application is concerned also with methods and compositions of matter thereof for the therapeutic management of the manifestations of psychotic disorders, psychoneurotic conditions, anxiety and tension in warm-blooded animals by administering compounds of the claimed invention.
The compounds of the present invention may be prepared by the following sequence: ##STR3## wherein R and R.
sub.
1 are as defined above.
The starting material, a substituted 5,10-dihydro-6H-pyrido[3,2-b]thieno[3,4-e][1,4]diazepin-6-thione (I), is prepared from the reaction of the corresponding 5,10-dihydro-6H-pyrido[3,2-b]thieno[3,4-e][1,4]diazepin-6-one (described in U.
S.
Pat.
No.
3,953,430) and phosphorus pentasulfide in a solvent such as pyridine at reflux.
This intermediate (I) is then converted to the correspondingly substituted 6-(methylthio)-10H-pyrido[3,2-b]thieno[3,4-e][1,4]diazepine (II) by reaction with a strong base such as sodium methoxide or sodium hydride and methyl iodide or methyl sulfate in a suitable solvent such as ethanol or dimethylformamide.
The latter reaction is carried out at from 25.
degree.
C to 45.
degree.
C for a period of from about 1/2 to 3 hours.
The intermediate (II) is converted to the corresponding 6-substituted piperazinyl-10H-pyrido[3,2-b]thieno[3,4-e][1,4]diazepine by reaction with the appropriate piperazine at reflux temperature either neat or in a solvent such as xylene containing a catalystic amount of acetic acid
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