CH567020A5 - 4h-s-triazolo (1,5-a) (1,4) benzodiazepine-2-carboxylic acid amide(s) - CNS inhibitors, anticonvulsants, tranquillizers, etc. - Google Patents
4h-s-triazolo (1,5-a) (1,4) benzodiazepine-2-carboxylic acid amide(s) - CNS inhibitors, anticonvulsants, tranquillizers, etc.Info
- Publication number
- CH567020A5 CH567020A5 CH173872A CH173872A CH567020A5 CH 567020 A5 CH567020 A5 CH 567020A5 CH 173872 A CH173872 A CH 173872A CH 173872 A CH173872 A CH 173872A CH 567020 A5 CH567020 A5 CH 567020A5
- Authority
- CH
- Switzerland
- Prior art keywords
- triazolo
- chloro
- benzodiazepine
- mol
- general formula
- Prior art date
Links
- 239000001961 anticonvulsive agent Substances 0.000 title description 5
- YICCAPNGTAHTGA-UHFFFAOYSA-N 4H-[1,2,4]triazolo[1,5-a][1,4]benzodiazepine-2-carboxylic acid Chemical compound C1N=CC2=CC=CC=C2N2N=C(C(=O)O)N=C21 YICCAPNGTAHTGA-UHFFFAOYSA-N 0.000 title description 2
- 229940125681 anticonvulsant agent Drugs 0.000 title description 2
- 239000003112 inhibitor Substances 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 150000003839 salts Chemical class 0.000 claims abstract description 16
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 13
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 8
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 52
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 45
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 18
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 16
- 238000002844 melting Methods 0.000 claims description 16
- 230000008018 melting Effects 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 239000000460 chlorine Substances 0.000 claims description 11
- 238000000354 decomposition reaction Methods 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000007858 starting material Substances 0.000 claims description 11
- FZVKANVQRBBDJA-UHFFFAOYSA-N 1,2-benzodiazepine-2-carboxamide Chemical compound NC(=O)N1C=CC=C2C=CC=CC2=N1 FZVKANVQRBBDJA-UHFFFAOYSA-N 0.000 claims description 10
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- CJYHJHPYTWFLHS-UHFFFAOYSA-N 1h-1,4-benzodiazepine-2-carboxamide Chemical compound N1C(C(=O)N)=CN=CC2=CC=CC=C21 CJYHJHPYTWFLHS-UHFFFAOYSA-N 0.000 claims description 9
- 150000007524 organic acids Chemical class 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 150000007522 mineralic acids Chemical class 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 7
- 239000011737 fluorine Chemical group 0.000 claims description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 6
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 235000005985 organic acids Nutrition 0.000 claims description 6
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 claims description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 150000003857 carboxamides Chemical class 0.000 claims description 4
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- 230000003647 oxidation Effects 0.000 claims description 4
- 238000007254 oxidation reaction Methods 0.000 claims description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 150000004965 peroxy acids Chemical class 0.000 claims description 3
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 2
- ALJUCXBQAGZWFT-UHFFFAOYSA-N 8-chloro-6-(2-fluorophenyl)-N-(2-hydroxyethyl)-4H-[1,2,4]triazolo[1,5-a][1,4]benzodiazepine-2-carboxamide Chemical compound C12=CC(Cl)=CC=C2N2N=C(C(=O)NCCO)N=C2CN=C1C1=CC=CC=C1F ALJUCXBQAGZWFT-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 125000005277 alkyl imino group Chemical group 0.000 claims description 2
- 229940049706 benzodiazepine Drugs 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- AVKAOVFFCRAZQV-UHFFFAOYSA-N 8-chloro-n,n-diethyl-6-phenyl-4h-[1,2,4]triazolo[1,5-a][1,4]benzodiazepine-2-carboxamide Chemical compound C12=CC(Cl)=CC=C2N2N=C(C(=O)N(CC)CC)N=C2CN=C1C1=CC=CC=C1 AVKAOVFFCRAZQV-UHFFFAOYSA-N 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 abstract description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 abstract 1
- 239000012965 benzophenone Substances 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 70
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- -1 2-hydroxypropyl Chemical group 0.000 description 43
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 20
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 19
- 239000002253 acid Substances 0.000 description 18
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 18
- 150000001735 carboxylic acids Chemical class 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- PHNMUQYFHNMYGN-UHFFFAOYSA-N 1h-1,4-benzodiazepine-2-carboxylic acid Chemical class N1C(C(=O)O)=CN=CC2=CC=CC=C21 PHNMUQYFHNMYGN-UHFFFAOYSA-N 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 229910052938 sodium sulfate Inorganic materials 0.000 description 10
- 235000011152 sodium sulphate Nutrition 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 7
- 150000001408 amides Chemical class 0.000 description 7
- 125000004494 ethyl ester group Chemical group 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 229940093915 gynecological organic acid Drugs 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 239000012954 diazonium Substances 0.000 description 4
- 150000001989 diazonium salts Chemical class 0.000 description 4
- 239000004312 hexamethylene tetramine Substances 0.000 description 4
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- GTGMXPIQRQSORU-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(2-fluorophenyl)methanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1F GTGMXPIQRQSORU-UHFFFAOYSA-N 0.000 description 3
- GPOKFLSWUBGZBM-UHFFFAOYSA-N 1,2-benzodiazepine-2-carboxylic acid Chemical compound OC(=O)N1C=CC=C2C=CC=CC2=N1 GPOKFLSWUBGZBM-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
- MCDPDIXQLHXPNV-UHFFFAOYSA-N 8-chloro-6-phenyl-4h-[1,2,4]triazolo[1,5-a][1,4]benzodiazepine-2-carboxylic acid Chemical compound C12=CC(Cl)=CC=C2N2N=C(C(=O)O)N=C2CN=C1C1=CC=CC=C1 MCDPDIXQLHXPNV-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 230000001773 anti-convulsant effect Effects 0.000 description 3
- 229960003965 antiepileptics Drugs 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 235000010288 sodium nitrite Nutrition 0.000 description 3
- ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 2
- XUZOBVGYAAVHDW-UHFFFAOYSA-N 1-(2-benzoyl-4-bromophenyl)-5-(chloromethyl)-1,2,4-triazole-3-carboxylic acid Chemical compound N1=C(C(=O)O)N=C(CCl)N1C1=CC=C(Br)C=C1C(=O)C1=CC=CC=C1 XUZOBVGYAAVHDW-UHFFFAOYSA-N 0.000 description 2
- 125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-N 3-chlorobenzoic acid Chemical compound OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
- PUBUWYSZWMXORC-UHFFFAOYSA-N 8-chloro-6-(2-chlorophenyl)-4h-[1,2,4]triazolo[1,5-a][1,4]benzodiazepine-2-carboxylic acid Chemical compound C12=CC(Cl)=CC=C2N2N=C(C(=O)O)N=C2CN=C1C1=CC=CC=C1Cl PUBUWYSZWMXORC-UHFFFAOYSA-N 0.000 description 2
- RCIDLVPAJRDWIW-UHFFFAOYSA-N 8-chloro-6-(2-chlorophenyl)-n,n-diethyl-4h-[1,2,4]triazolo[1,5-a][1,4]benzodiazepine-2-carboxamide Chemical compound C12=CC(Cl)=CC=C2N2N=C(C(=O)N(CC)CC)N=C2CN=C1C1=CC=CC=C1Cl RCIDLVPAJRDWIW-UHFFFAOYSA-N 0.000 description 2
- DOIKDDSTKNFGID-UHFFFAOYSA-N 8-chloro-6-(2-fluorophenyl)-4h-[1,2,4]triazolo[1,5-a][1,4]benzodiazepine-2-carboxylic acid Chemical compound C12=CC(Cl)=CC=C2N2N=C(C(=O)O)N=C2CN=C1C1=CC=CC=C1F DOIKDDSTKNFGID-UHFFFAOYSA-N 0.000 description 2
- NGWWJBCDRRMIPL-UHFFFAOYSA-N 8-nitro-6-phenyl-4h-[1,2,4]triazolo[1,5-a][1,4]benzodiazepine-2-carboxylic acid Chemical compound C12=CC([N+]([O-])=O)=CC=C2N2N=C(C(=O)O)N=C2CN=C1C1=CC=CC=C1 NGWWJBCDRRMIPL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical class CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- NRMOBHGSHDKJLW-UHFFFAOYSA-N [2-amino-5-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound NC1=CC=C(C(F)(F)F)C=C1C(=O)C1=CC=CC=C1 NRMOBHGSHDKJLW-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
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- QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 2
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- PZPZDEIASIKHPY-UHFFFAOYSA-N (2-amino-5-nitrophenyl)-phenylmethanone Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 PZPZDEIASIKHPY-UHFFFAOYSA-N 0.000 description 1
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- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
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- PADHVNCHPHEBPA-UHFFFAOYSA-N 8-bromo-n,n-dimethyl-6-phenyl-4h-[1,2,4]triazolo[1,5-a][1,4]benzodiazepine-2-carboxamide Chemical compound C12=CC(Br)=CC=C2N2N=C(C(=O)N(C)C)N=C2CN=C1C1=CC=CC=C1 PADHVNCHPHEBPA-UHFFFAOYSA-N 0.000 description 1
- PVNXUCAAXXYFKB-UHFFFAOYSA-N 8-chloro-6-(2-chlorophenyl)-n-methyl-4h-[1,2,4]triazolo[1,5-a][1,4]benzodiazepine-2-carboxamide Chemical compound C12=CC(Cl)=CC=C2N2N=C(C(=O)NC)N=C2CN=C1C1=CC=CC=C1Cl PVNXUCAAXXYFKB-UHFFFAOYSA-N 0.000 description 1
- QMVLSRGNUFTATB-UHFFFAOYSA-N 8-chloro-6-(2-fluorophenyl)-4h-[1,2,4]triazolo[1,5-a][1,4]benzodiazepine-2-carbonyl chloride Chemical compound FC1=CC=CC=C1C1=NCC2=NC(C(Cl)=O)=NN2C2=CC=C(Cl)C=C12 QMVLSRGNUFTATB-UHFFFAOYSA-N 0.000 description 1
- JERMNTDWLDFEGH-UHFFFAOYSA-N 8-chloro-6-(2-fluorophenyl)-4h-[1,2,4]triazolo[1,5-a][1,4]benzodiazepine-2-carboxamide Chemical compound C12=CC(Cl)=CC=C2N2N=C(C(=O)N)N=C2CN=C1C1=CC=CC=C1F JERMNTDWLDFEGH-UHFFFAOYSA-N 0.000 description 1
- LJMQBIZMGZIAST-UHFFFAOYSA-N 8-chloro-6-(2-fluorophenyl)-n,n-dimethyl-4h-[1,2,4]triazolo[1,5-a][1,4]benzodiazepine-2-carboxamide Chemical compound C12=CC(Cl)=CC=C2N2N=C(C(=O)N(C)C)N=C2CN=C1C1=CC=CC=C1F LJMQBIZMGZIAST-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- WVMWALYQFUJQSC-UHFFFAOYSA-N C(C)OC(C(C(=O)OCC)N=NC1=C(C=C(C=C1)Cl)C(C1=CC=CC=C1)=O)=O Chemical compound C(C)OC(C(C(=O)OCC)N=NC1=C(C=C(C=C1)Cl)C(C1=CC=CC=C1)=O)=O WVMWALYQFUJQSC-UHFFFAOYSA-N 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
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- 241001465754 Metazoa Species 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 1
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- 241001279009 Strychnos toxifera Species 0.000 description 1
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- 150000001447 alkali salts Chemical class 0.000 description 1
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- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
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- 125000001246 bromo group Chemical group Br* 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
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- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
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- PSOISAZMWBBMKT-UHFFFAOYSA-N diethyl 2-[(2-benzoyl-4-nitrophenyl)diazenyl]-2-[(2-chloroacetyl)amino]propanedioate Chemical compound CCOC(=O)C(NC(=O)CCl)(C(=O)OCC)N=NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 PSOISAZMWBBMKT-UHFFFAOYSA-N 0.000 description 1
- WMNDKWKOEAXOSM-UHFFFAOYSA-N diethyl 2-[(2-chloroacetyl)amino]-2-[[4-chloro-2-(2-fluorobenzoyl)phenyl]diazenyl]propanedioate Chemical compound CCOC(=O)C(NC(=O)CCl)(C(=O)OCC)N=NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1F WMNDKWKOEAXOSM-UHFFFAOYSA-N 0.000 description 1
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- VVOISGODVGAYPS-UHFFFAOYSA-N ethyl 1-(2-benzoyl-4-nitrophenyl)-5-(chloromethyl)-1,2,4-triazole-3-carboxylate Chemical compound N1=C(C(=O)OCC)N=C(CCl)N1C1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 VVOISGODVGAYPS-UHFFFAOYSA-N 0.000 description 1
- DHZYWCBUDKTLGD-UHFFFAOYSA-N ethyl 1h-1,2,4-triazole-5-carboxylate Chemical compound CCOC(=O)C1=NC=NN1 DHZYWCBUDKTLGD-UHFFFAOYSA-N 0.000 description 1
- QIHNBRTVYICNTQ-UHFFFAOYSA-N ethyl 1h-1,4-benzodiazepine-2-carboxylate Chemical compound N1C(C(=O)OCC)=CN=CC2=CC=CC=C21 QIHNBRTVYICNTQ-UHFFFAOYSA-N 0.000 description 1
- UTJLOUUVFHZACW-UHFFFAOYSA-N ethyl 6-(2-fluorophenyl)-8-nitro-4H-[1,2,4]triazolo[1,5-a][1,4]benzodiazepine-2-carboxylate Chemical compound C12=CC([N+]([O-])=O)=CC=C2N2N=C(C(=O)OCC)N=C2CN=C1C1=CC=CC=C1F UTJLOUUVFHZACW-UHFFFAOYSA-N 0.000 description 1
- RRZCWBXIPGPEBU-UHFFFAOYSA-N ethyl 8-nitro-6-phenyl-4h-[1,2,4]triazolo[1,5-a][1,4]benzodiazepine-2-carboxylate Chemical compound C12=CC([N+]([O-])=O)=CC=C2N2N=C(C(=O)OCC)N=C2CN=C1C1=CC=CC=C1 RRZCWBXIPGPEBU-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
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- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000005191 hydroxyalkylamino group Chemical group 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- NBCMDDVCPGVZPY-UHFFFAOYSA-N n,n-dimethyl-8-nitro-6-phenyl-4h-[1,2,4]triazolo[1,5-a][1,4]benzodiazepine-2-carboxamide Chemical compound C12=CC([N+]([O-])=O)=CC=C2N2N=C(C(=O)N(C)C)N=C2CN=C1C1=CC=CC=C1 NBCMDDVCPGVZPY-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229960005453 strychnine Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/32—Monoazo dyes prepared by diazotising and coupling from coupling components containing a reactive methylene group
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (48)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE795020D BE795020A (fr) | 1972-02-07 | Procede de preparation de nouvelles diazepines | |
| CH173872A CH567020A5 (en) | 1972-02-07 | 1972-02-07 | 4h-s-triazolo (1,5-a) (1,4) benzodiazepine-2-carboxylic acid amide(s) - CNS inhibitors, anticonvulsants, tranquillizers, etc. |
| FI99/73A FI54310C (fi) | 1972-02-07 | 1973-01-15 | Foerfarande foer framstaellning av nya saosom laekemedel anvaendbara 6-fenyl-4h-s-triazolo(1,5-a)(1,4)bensodiazepin-2-karboxamider |
| SE7300689A SE402012B (sv) | 1972-02-07 | 1973-01-18 | Analogiforfarande for framstellning av s-triazolo(1,5-a)(1,4)diazepinderivat |
| NO275/73A NO135422C (cs) | 1972-02-07 | 1973-01-23 | |
| IE99/73A IE37250B1 (en) | 1972-02-07 | 1973-01-23 | Diazepine derivatives and processes for their production |
| IL41375A IL41375A (en) | 1972-02-07 | 1973-01-23 | 6-phenyl-4h-s-triazolo(1,5-alpha)(1,4)benzodiazepine-2-carboxamides,their production and pharmaceutical compositions containing them |
| ZA730531A ZA73531B (en) | 1972-02-07 | 1973-01-24 | New diazepine derivatives and processes for their production |
| DE2304307A DE2304307A1 (de) | 1972-02-07 | 1973-01-30 | Neue diazepinderivate und verfahren zu ihrer herstellung |
| US328815*A US3870714A (en) | 1972-02-07 | 1973-01-31 | Certain 6-phenyl-4h-s-triazolo{8 1,5-a{9 {8 1,4{9 benzodiazepine-2-carboxamides |
| CA162,532A CA1003412A (en) | 1972-02-07 | 1973-01-31 | Triazolo benzodiazepines |
| SU1878321A SU520918A3 (ru) | 1972-02-07 | 1973-01-31 | Способ получени производных диазепина |
| ES411321A ES411321A1 (es) | 1972-02-07 | 1973-02-05 | Procedimiento para la obtencion de nuevos derivados de dia-zepina. |
| YU00291/73A YU29173A (en) | 1972-02-07 | 1973-02-05 | Process for preparing new diazepine derivatives |
| NL7301601A NL7301601A (cs) | 1972-02-07 | 1973-02-05 | |
| AU51780/73A AU476040B2 (en) | 1972-02-07 | 1973-02-05 | New diazepine derivatives and processes for their production |
| FR7304099A FR2181706B1 (cs) | 1972-02-07 | 1973-02-06 | |
| PL1973160619A PL89204B1 (en) | 1972-02-07 | 1973-02-06 | 4h-s-triazolo (1,5-a) (1,4) benzodiazepine-2-carboxylic acid amide(s) - CNS inhibitors, anticonvulsants, tranquillizers, etc.[CH567020A5] |
| DK62173A DK143277C (da) | 1972-02-07 | 1973-02-06 | Analogifremgangsmaade til fremstilling af s-triazolo(1,5-a)(1,4)benzodiazepinderivater eller 5-oxider eller syreadditionssalte deraf |
| EG46/73A EG10822A (en) | 1972-02-07 | 1973-02-06 | Process for the production of new diazepine derivatives |
| DD168394A DD105616A5 (cs) | 1972-02-07 | 1973-02-06 | |
| PL1973178148A PL92656B1 (en) | 1972-02-07 | 1973-02-06 | 4h-s-triazolo (1,5-a) (1,4) benzodiazepine-2-carboxylic acid amide(s) - CNS inhibitors, anticonvulsants, tranquillizers, etc.[CH567020A5] |
| AT103873A AT328454B (de) | 1972-02-07 | 1973-02-06 | Verfahren zur herstellung von neuen diazepinderivaten sowie deren 5-oxide und saureadditionssalze |
| AR246440A AR197802A1 (es) | 1972-02-07 | 1973-02-06 | Procedimiento para la obtencion de nuevos derivados de diazepina |
| PL1973178147A PL94159B1 (en) | 1972-02-07 | 1973-02-06 | 4h-s-triazolo (1,5-a) (1,4) benzodiazepine-2-carboxylic acid amide(s) - CNS inhibitors, anticonvulsants, tranquillizers, etc.[CH567020A5] |
| OA54824A OA04525A (fr) | 1972-02-07 | 1973-02-06 | Procédé de préparation de nouvelles diazépines. |
| HUCI1336A HU166827B (cs) | 1972-02-07 | 1973-02-06 | |
| CS7600006548A CS186798B2 (en) | 1972-02-07 | 1973-02-07 | Method of producing novel 2-aminocarbonyl-6-aryl-4h-s-triazole /1,5-a/ /1,4/benzdiazepines |
| CS7300000905A CS186770B2 (en) | 1972-02-07 | 1973-02-07 | Method of producing novel 2-aminocarbonyl-6-aryl-4h-s-triazole/1,5-a/ /1,4/benzdiazepines |
| CS7600006547A CS186797B2 (en) | 1972-02-07 | 1973-02-07 | Method of producing novel 2-aminocarbonyl-6-aryl-4h-s-triazole1,5-a/ /1,4/benzdiazepines |
| GB608173A GB1422266A (en) | 1972-02-07 | 1973-02-07 | Diazepine derivatives and processes for their production |
| GB3266375A GB1422267A (en) | 1972-02-07 | 1973-02-07 | Triazole derivatives |
| AR250754A AR200500A1 (es) | 1972-02-07 | 1973-10-29 | Procedimiento para la obtencion de nuevos derivados de diazapina |
| AR250753A AR197835A1 (es) | 1972-02-07 | 1973-10-29 | Procedimiento para la obtencion de nuevos derivados de diazepina |
| SU2067388A SU552028A3 (ru) | 1972-02-07 | 1974-10-09 | Способ получени производных диазепина или их 5-окисей, или их солей |
| SU2068917A SU555851A3 (ru) | 1972-02-07 | 1974-10-09 | Способ получени производных диазепина или их солей 5-окисей, или их солей |
| US05/535,480 US4027029A (en) | 1972-02-07 | 1974-12-23 | Diazepine derivatives |
| AT231775A AT330191B (de) | 1972-02-07 | 1975-03-26 | Verfahren zur herstellung neuer diazepinderivate sowie deren 5-oxide und saureadditionssalze |
| AT231875A AT330192B (de) | 1972-02-07 | 1975-03-26 | Verfahren zur herstellung neuer diazepinderivate sowie deren 5-oxide und saureadditionssalze |
| ES438600A ES438600A1 (es) | 1972-02-07 | 1975-06-16 | Procedimiento para la obtencion de nuevos derivados de dia- zepina. |
| ES438602A ES438602A1 (es) | 1972-02-07 | 1975-06-16 | Procedimiento para la obtencion de nuevos derivados de dia- zepina. |
| ES438601A ES438601A1 (es) | 1972-02-07 | 1975-06-16 | Procedimiento para la obtencion de nuevos derivados de dia- zepina. |
| US05/765,573 US4111950A (en) | 1972-02-07 | 1977-02-04 | Triazolyl benzophenones |
| KE2910A KE2910A (en) | 1972-02-07 | 1978-12-24 | Diazepine derivatives and processes for their production |
| HK38/79A HK3879A (en) | 1972-02-07 | 1979-01-18 | Diazepine derivatives and processes for their production |
| YU02278/79A YU227879A (en) | 1972-02-07 | 1979-09-19 | Process for preparing new diazepine derivatives |
| YU02277/79A YU227779A (en) | 1972-02-07 | 1979-09-19 | Process for preparing new diazepine derivatives |
| MY23/79A MY7900023A (en) | 1972-02-07 | 1979-12-30 | Diazepine derivatives and processes for their production |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH173872A CH567020A5 (en) | 1972-02-07 | 1972-02-07 | 4h-s-triazolo (1,5-a) (1,4) benzodiazepine-2-carboxylic acid amide(s) - CNS inhibitors, anticonvulsants, tranquillizers, etc. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH567020A5 true CH567020A5 (en) | 1975-09-30 |
Family
ID=4217420
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH173872A CH567020A5 (en) | 1972-02-07 | 1972-02-07 | 4h-s-triazolo (1,5-a) (1,4) benzodiazepine-2-carboxylic acid amide(s) - CNS inhibitors, anticonvulsants, tranquillizers, etc. |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT328454B (cs) |
| AU (1) | AU476040B2 (cs) |
| CH (1) | CH567020A5 (cs) |
| CS (3) | CS186798B2 (cs) |
| ES (4) | ES411321A1 (cs) |
| HU (1) | HU166827B (cs) |
| PL (3) | PL92656B1 (cs) |
| SU (3) | SU520918A3 (cs) |
| ZA (1) | ZA73531B (cs) |
-
1972
- 1972-02-07 CH CH173872A patent/CH567020A5/de not_active IP Right Cessation
-
1973
- 1973-01-24 ZA ZA730531A patent/ZA73531B/xx unknown
- 1973-01-31 SU SU1878321A patent/SU520918A3/ru active
- 1973-02-05 ES ES411321A patent/ES411321A1/es not_active Expired
- 1973-02-05 AU AU51780/73A patent/AU476040B2/en not_active Expired
- 1973-02-06 PL PL1973178148A patent/PL92656B1/pl unknown
- 1973-02-06 HU HUCI1336A patent/HU166827B/hu unknown
- 1973-02-06 PL PL1973160619A patent/PL89204B1/pl unknown
- 1973-02-06 PL PL1973178147A patent/PL94159B1/pl unknown
- 1973-02-06 AT AT103873A patent/AT328454B/de not_active IP Right Cessation
- 1973-02-07 CS CS7600006548A patent/CS186798B2/cs unknown
- 1973-02-07 CS CS7600006547A patent/CS186797B2/cs unknown
- 1973-02-07 CS CS7300000905A patent/CS186770B2/cs unknown
-
1974
- 1974-10-09 SU SU2068917A patent/SU555851A3/ru active
- 1974-10-09 SU SU2067388A patent/SU552028A3/ru active
-
1975
- 1975-06-16 ES ES438602A patent/ES438602A1/es not_active Expired
- 1975-06-16 ES ES438601A patent/ES438601A1/es not_active Expired
- 1975-06-16 ES ES438600A patent/ES438600A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SU555851A3 (ru) | 1977-04-25 |
| AU5178073A (en) | 1974-08-08 |
| ES438600A1 (es) | 1977-03-01 |
| SU552028A3 (ru) | 1977-03-25 |
| CS186770B2 (en) | 1978-12-29 |
| ES411321A1 (es) | 1976-04-01 |
| CS186797B2 (en) | 1978-12-29 |
| PL94159B1 (en) | 1977-07-30 |
| ZA73531B (en) | 1973-10-31 |
| PL92656B1 (en) | 1977-04-30 |
| ATA103873A (de) | 1975-06-15 |
| AU476040B2 (en) | 1976-09-09 |
| HU166827B (cs) | 1975-06-28 |
| AT328454B (de) | 1976-03-25 |
| ES438601A1 (es) | 1977-04-01 |
| ES438602A1 (es) | 1977-03-16 |
| SU520918A3 (ru) | 1976-07-05 |
| CS186798B2 (en) | 1978-12-29 |
| PL89204B1 (en) | 1976-11-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |