IL42416A - 6-phenyl-4h-s-triazolo(4,3-alpha)(1,4)benzodiazepine and n-oxide derivatives,their preparation and pharmaceutical compositions containing them - Google Patents

Claims (1)

1. CLAIMS Ci.."■ Benzodiazepine derivatives of the general formula. wherein Y represents one of the groups R, R^ and R^ represent hydrogen or lower alkyl, R^ represents phenyl or halophenyl. represents hydrogen, lower alkyl, hydroxy or lower alkanoylox , -R^. an&Rg together represent a group -OI^CI^-, removable by conventional-hydrolyzing techniqAies-.-and-.n represents the integer 0 or 1 with the proviso, that n represents the integer 0, when R^ represents hydroxy or lower alkanoyloxy, pharmaceutically jacceptable acid addition salts thereof . 42416/2 2. Benzodiazepine derivatives -according to claim wherein R^ is hydrogen. 3. Benzodiazepine derivatives according to claim or 82 wherein R. is hydrogen. 4. Benzodiazepine derivatives according to any one of claims 1-3 wherein R, is phenyl or halophenyl. 5. Benzodiazepine derivatives according to claim wherein R^ is o-halophenyl. ;6. Benzodiazepine derivatives according to claim 5 wherein R^ is o-fluorophenyl . '7. Benzodiazepine derivatives according to any one of -claims |1-6: ! wherein R-and R^are-methyl.. 3. Benzodiazepine derivatives according to any one of claims I 1-7 wherein n is the integer 0. '•9. 6-(2-fluorophenyl)-8-(1-hydroxyethyl)-l-methy1-4H-s-triazolo[ 4 , 3-a] [ 1, 4]benzodiazepine . 42416/2 10. 1-methyl-8-(2-methyl-1 ,3-dioxolan-2-yl)-6- " phenyl-4H-s-triazoio 4,3-a7/ f.^benzodiazepine. 11. 8-acetyl-1-methyl-6-phenyl-4H-s-triazolo 4,3-a7/T,47 benzodiazepine . 12. 1 -methyl-8- ( 2-methyi-1 , 3-dioxolan-2-yl)-6-phenyl- 4H-s-triazolo 4,3-a7jl ,,.7benzodiazepine-5-oxide. 13. 8-acet l-1-methyl-6-phenyl-4H-s-triazolo 4,3-a7 f47 benzodiazepine-5-oxide . 14. 4-acetoxy-8-acetyl-1 -methyl-6-phenyl-4H-s-triazolo- ' 15i 8-(1 -hydroxy-ethyl)-1 -methyl-6-phenyl-4H-s-triazolo-Z f 3-a7/l ,47benzodiazepine-5-oxide . 16. 8-acetyl-1 -methyl-^-hydroxy-e-phenyl-^H-s- . 17. Benzodiazepine derivatives of formula I in Claim 1 and pharmaceutically acceptable salts thereof, substantially as described herein with reference to the Examples. 18. A process for preparing benzodiazepine derivatives of the general formula I -in Claim- 1- and of pharmaceutically acce -able--acid- addition salts thereof, which process comprises a) for preparing compounds of the general formula wherein Z represents the group and n, R, R^, R^t R^, R^, R^ and Rg have the meaning indicated above, treating a compound of the general formula wherein Rrj represents lower alkyl and n, Z, R, R^, Rj, R^, R and Rg have the meaning indicated above, with a lower alkanoyl hydrazide, or b) for preparing compounds of the general formula wherein n, R, . R^, and ^ have the meaning indicated above, hydrolyzing a compound of the general formula wherein n, R, R^t ^> R^, R^ and Rg have the meaning indicated above, or c) for preparing compounds of the formula I above, R^ represents lower alkanoyloxy, n is 0 and Y, R, R-j, R^ and Rg have the meaning indicated above, treating a compound of the general formula wherein Y, R, R^, R^, R^> R^ and Rg have the meaning indicated above, with a lower alkanoyl group providing agent, or d) for preparing compounds of the formula I above, wherein R^ represents hydroxy, n is 0 and Y, R, R.^, R2, R^, R^ and Rg have the meaning indicated above, hydrolyzing a compound of the general formula wherein Y, R, R, , R», R, , R._ and R ' 1' 2 3 5 1 the meaning indicated above and Rg presents lower alkanoyloxy, or e) for preparing compounds of the formula I above, wherein R^ represents hydrogen or lower alkyl and n represents the integer 0, deoxygenating a corresponding N-oxide, or f ) for preparing compounds of the general formula wherein n, R, R2, j. and R^ have the meaning indicated above, reducing a compound of the formula lb above, or g) for preparing compounds of the general formula wherein R'^ represents lower alkyl and n, R, R2> R^ and R^ have the meaning indicated above, treating a compound of the formula lb above with a lower alkyl lithium, or h) for preparing compounds of the formula lb above oxidizing a compound of the formula Ie above, and i) if desired, converting a product obtained into a pharmaceutically acceptable acid addition salt. 19. A process as claimed in claim 18 wherei-n R^ ■is ·\ hydrogen. 20. A process as claimed in claim 18 "or 19 wherein B^ is hydrogen. 21* A process as claimed in any one of claims 18-20 wherein R-j is phenyl or halophenyl. 22. A process as claimed in claim 21 wherein R^ is o-halophenyl. 23. A process as claimed in claim 22 wherein is o-fluorophenyl. 24. A process as claimed in any one of claims 18-23 wherein R and are methyl. 25· A process as claimed in. any one of claims 18-24 wherein n is the integer 0. 26. A process as claimed in claim 18 herein any of the compound's of Claims 9 to 17 is prepared. 27. A process for the preparation of benzodiazepine derivatives of the general formula I as defined in claim 1 as hereinbefore particularly described, especially with -reference to the foregoing:Examples: 1 to 9. 28. -Benzodiazepine derivatives, of the general formula I in claim 1 when prepared by a process according to any. one of claims 18-27. 29._ Compositions having anticonvulsant, muscle relaxant and sedative properties, containing a benzodiazepine derivative of the general formula I as defined in claim 1 or a pharmaceutically acceptable acid addition salt thereof and a carrier.