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
6-phenyl-4h-s-triazolo(4,3-alpha)(1,4)benzodiazepine and n-oxide derivatives,their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL42416A IL42416A IL42416A IL4241673A IL42416A IL 42416 A IL42416 A IL 42416A IL 42416 A IL42416 A IL 42416A IL 4241673 A IL4241673 A IL 4241673A IL 42416 A IL42416 A IL 42416A
- Authority
- IL
- Israel
- Prior art keywords
- general formula
- phenyl
- benzodiazepine
- methyl
- formula
- Prior art date
Links
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical compound N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 title claims 2
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 16
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims 12
- 150000001557 benzodiazepines Chemical class 0.000 claims 12
- 238000000034 method Methods 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 7
- 239000001257 hydrogen Substances 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- 239000002253 acid Substances 0.000 claims 3
- 125000004423 acyloxy group Chemical group 0.000 claims 3
- 125000005059 halophenyl group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- -1 alkyl lithium Chemical compound 0.000 claims 1
- 230000001773 anti-convulsant effect Effects 0.000 claims 1
- 239000001961 anticonvulsive agent Substances 0.000 claims 1
- 229960003965 antiepileptics Drugs 0.000 claims 1
- 229940049706 benzodiazepine Drugs 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 230000003635 deoxygenating effect Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000003158 myorelaxant agent Substances 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 230000001624 sedative effect Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
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.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27143372A | 1972-07-13 | 1972-07-13 | |
| US35582973A | 1973-04-30 | 1973-04-30 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42416A0 IL42416A0 (en) | 1973-07-30 |
| IL42416A true IL42416A (en) | 1976-06-30 |
Family
ID=26954889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42416A IL42416A (en) | 1972-07-13 | 1973-05-31 | 6-phenyl-4h-s-triazolo(4,3-alpha)(1,4)benzodiazepine and n-oxide derivatives,their preparation and pharmaceutical compositions containing them |
Country Status (10)
| Country | Link |
|---|---|
| AU (1) | AU5667373A (en) |
| DD (1) | DD107691A5 (en) |
| DE (1) | DE2335282A1 (en) |
| ES (1) | ES416815A1 (en) |
| FR (1) | FR2192823A1 (en) |
| GB (2) | GB1435982A (en) |
| IE (1) | IE37889B1 (en) |
| IL (1) | IL42416A (en) |
| LU (1) | LU67988A1 (en) |
| NL (1) | NL7309566A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE434615T1 (en) | 2000-11-21 | 2009-07-15 | Janssen Pharmaceutica Nv | FARNESYLTRANSFERASE INHIBITING BENZOHETROCYCLIC DERIVATIVES |
-
1973
- 1973-05-31 IL IL42416A patent/IL42416A/en unknown
- 1973-06-07 AU AU56673/73A patent/AU5667373A/en not_active Expired
- 1973-07-09 IE IE1150/73A patent/IE37889B1/en unknown
- 1973-07-09 NL NL7309566A patent/NL7309566A/xx unknown
- 1973-07-11 LU LU67988A patent/LU67988A1/xx unknown
- 1973-07-11 DE DE19732335282 patent/DE2335282A1/en active Pending
- 1973-07-11 FR FR7325368A patent/FR2192823A1/fr not_active Withdrawn
- 1973-07-12 GB GB1897375A patent/GB1435982A/en not_active Expired
- 1973-07-12 GB GB3328973A patent/GB1435981A/en not_active Expired
- 1973-07-12 ES ES416815A patent/ES416815A1/en not_active Expired
- 1973-07-13 DD DD172327A patent/DD107691A5/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE2335282A1 (en) | 1974-01-31 |
| DD107691A5 (en) | 1974-08-12 |
| NL7309566A (en) | 1974-01-15 |
| IL42416A0 (en) | 1973-07-30 |
| AU5667373A (en) | 1974-12-12 |
| IE37889B1 (en) | 1977-11-09 |
| FR2192823A1 (en) | 1974-02-15 |
| ES416815A1 (en) | 1976-05-16 |
| IE37889L (en) | 1974-01-13 |
| GB1435982A (en) | 1976-05-19 |
| GB1435981A (en) | 1976-05-19 |
| LU67988A1 (en) | 1975-04-11 |
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