CH513886A - Verfahren zur Herstellung von Benzodiazepin-Derivaten - Google Patents
Verfahren zur Herstellung von Benzodiazepin-DerivatenInfo
- Publication number
- CH513886A CH513886A CH115269A CH115269A CH513886A CH 513886 A CH513886 A CH 513886A CH 115269 A CH115269 A CH 115269A CH 115269 A CH115269 A CH 115269A CH 513886 A CH513886 A CH 513886A
- Authority
- CH
- Switzerland
- Prior art keywords
- hydrogen
- phenyl
- formula
- halogen
- benzodiazepin
- Prior art date
Links
- LLPGEPRZHOMDHC-UHFFFAOYSA-N 2-(c-phenylcarbonohydrazonoyl)aniline Chemical class C=1C=CC=C(N)C=1C(=NN)C1=CC=CC=C1 LLPGEPRZHOMDHC-UHFFFAOYSA-N 0.000 title abstract 2
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- 150000007857 hydrazones Chemical class 0.000 claims abstract description 10
- 230000002378 acidificating effect Effects 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Chemical group 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical group [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 4
- 150000002431 hydrogen Chemical group 0.000 claims 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 abstract description 2
- 239000001961 anticonvulsive agent Substances 0.000 abstract description 2
- 229940125681 anticonvulsant agent Drugs 0.000 abstract 1
- 239000012965 benzophenone Substances 0.000 abstract 1
- 229940035363 muscle relaxants Drugs 0.000 abstract 1
- 239000003158 myorelaxant agent Substances 0.000 abstract 1
- 229940125723 sedative agent Drugs 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- -1 for example Chemical class 0.000 description 14
- 239000000243 solution Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- QYCSNMDOZNUZIT-UHFFFAOYSA-N benzhydrylidenehydrazine Chemical compound C=1C=CC=CC=1C(=NN)C1=CC=CC=C1 QYCSNMDOZNUZIT-UHFFFAOYSA-N 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- 238000007363 ring formation reaction Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- UDLAUVFRZXIQJS-UHFFFAOYSA-N 1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N1C(=O)CN=CC2=CC=CC=C21 UDLAUVFRZXIQJS-UHFFFAOYSA-N 0.000 description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 2
- DBFLXAXACNTBEP-UHFFFAOYSA-N 5-phenyl-3h-1,4-benzodiazepine Chemical class N=1CC=NC2=CC=CC=C2C=1C1=CC=CC=C1 DBFLXAXACNTBEP-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005597 hydrazone group Chemical group 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- PLZWYQYDWCXHTF-UHFFFAOYSA-N 1-methyl-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(C)C2=CC=CC=C2C=1C1=CC=CC=C1 PLZWYQYDWCXHTF-UHFFFAOYSA-N 0.000 description 1
- NTVANYIWXRUGQR-UHFFFAOYSA-N 5-(4-chlorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C1=CC(Cl)=CC=C1C1=NCC(=O)NC2=CC=CC=C12 NTVANYIWXRUGQR-UHFFFAOYSA-N 0.000 description 1
- RMNQMFPFGLLSPE-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound FC(F)(F)C1=CC=CC(C=2C3=CC=CC=C3NC(=O)CN=2)=C1 RMNQMFPFGLLSPE-UHFFFAOYSA-N 0.000 description 1
- KJLDVCXHGDQPAB-UHFFFAOYSA-N 5-[4-(trifluoromethyl)phenyl]-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C1=CC(C(F)(F)F)=CC=C1C1=NCC(=O)NC2=CC=CC=C12 KJLDVCXHGDQPAB-UHFFFAOYSA-N 0.000 description 1
- IVUAAOBNUNMJQC-UHFFFAOYSA-N 5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC=CC=C2NC(=O)CN=C1C1=CC=CC=C1 IVUAAOBNUNMJQC-UHFFFAOYSA-N 0.000 description 1
- AOJRGBWRJGTLDT-UHFFFAOYSA-N 5-phenyl-8-(trifluoromethyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C=1C(C(F)(F)F)=CC=C2C=1NC(=O)CN=C2C1=CC=CC=C1 AOJRGBWRJGTLDT-UHFFFAOYSA-N 0.000 description 1
- WEPBMRWHJMFXGG-UHFFFAOYSA-N 7,8-dimethyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C1=2C=C(C)C(C)=CC=2NC(=O)CN=C1C1=CC=CC=C1 WEPBMRWHJMFXGG-UHFFFAOYSA-N 0.000 description 1
- LODQZIQLZDHYJG-UHFFFAOYSA-N 7,9-dichloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(Cl)=CC(Cl)=C2NC(=O)CN=C1C1=CC=CC=C1 LODQZIQLZDHYJG-UHFFFAOYSA-N 0.000 description 1
- KVXRLJHLTJKYKB-UHFFFAOYSA-N 7-bromo-5-(4-methylphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C1=CC(C)=CC=C1C1=NCC(=O)NC2=CC=C(Br)C=C12 KVXRLJHLTJKYKB-UHFFFAOYSA-N 0.000 description 1
- SRDIBKOFJZSMMA-UHFFFAOYSA-N 7-bromo-8-methoxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C1=2C=C(Br)C(OC)=CC=2NC(=O)CN=C1C1=CC=CC=C1 SRDIBKOFJZSMMA-UHFFFAOYSA-N 0.000 description 1
- PMOYAPWQLZTKJB-UHFFFAOYSA-N 7-chloro-1-ethyl-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 PMOYAPWQLZTKJB-UHFFFAOYSA-N 0.000 description 1
- IKDQDTVOEWNZKV-UHFFFAOYSA-N 7-chloro-1-methyl-5-(2-methylphenyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1C IKDQDTVOEWNZKV-UHFFFAOYSA-N 0.000 description 1
- VMRHOEBUTQIEKP-UHFFFAOYSA-N 7-chloro-5-(2-methoxyphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound COC1=CC=CC=C1C1=NCC(=O)NC2=CC=C(Cl)C=C12 VMRHOEBUTQIEKP-UHFFFAOYSA-N 0.000 description 1
- PLSKGUKSIDTEPG-UHFFFAOYSA-N 7-chloro-5-(2-methoxyphenyl)-1-methyl-3H-1,4-benzodiazepin-2-one Chemical compound COC1=C(C=CC=C1)C1=NCC(=O)N(C)C2=CC=C(Cl)C=C12 PLSKGUKSIDTEPG-UHFFFAOYSA-N 0.000 description 1
- AOOWAUAQVUYDCR-UHFFFAOYSA-N 7-chloro-5-(2-methylphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound CC1=CC=CC=C1C1=NCC(=O)NC2=CC=C(Cl)C=C12 AOOWAUAQVUYDCR-UHFFFAOYSA-N 0.000 description 1
- ZKDHYCJJSORAST-UHFFFAOYSA-N 7-chloro-5-(3-fluorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound FC1=CC=CC(C=2C3=CC(Cl)=CC=C3NC(=O)CN=2)=C1 ZKDHYCJJSORAST-UHFFFAOYSA-N 0.000 description 1
- JPSGKFVCUQLFJS-UHFFFAOYSA-N 7-chloro-5-(3-methoxyphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound COC1=CC=CC(C=2C3=CC(Cl)=CC=C3NC(=O)CN=2)=C1 JPSGKFVCUQLFJS-UHFFFAOYSA-N 0.000 description 1
- XKAHDJVCUSNHTE-UHFFFAOYSA-N 7-chloro-5-(4-chlorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C1=CC(Cl)=CC=C1C1=NCC(=O)NC2=CC=C(Cl)C=C12 XKAHDJVCUSNHTE-UHFFFAOYSA-N 0.000 description 1
- BWQOGLAANRWTBZ-UHFFFAOYSA-N 7-chloro-5-(4-methoxyphenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C1=CC(OC)=CC=C1C1=NCC(=O)NC2=CC=C(Cl)C=C12 BWQOGLAANRWTBZ-UHFFFAOYSA-N 0.000 description 1
- JZWOKDTXYPEJEW-UHFFFAOYSA-N 7-chloro-5-phenyl-2,3-dihydro-1h-1,4-benzodiazepine Chemical compound C12=CC(Cl)=CC=C2NCCN=C1C1=CC=CC=C1 JZWOKDTXYPEJEW-UHFFFAOYSA-N 0.000 description 1
- XCLIOOLMKFFEIX-UHFFFAOYSA-N 7-chloro-9-methylsulfanyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound CSC1=C2NC(=O)CN=C(C3=CC=CC=C3)C2=CC(Cl)=C1 XCLIOOLMKFFEIX-UHFFFAOYSA-N 0.000 description 1
- PEACRWGRSQUWBX-UHFFFAOYSA-N 7-methoxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(OC)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 PEACRWGRSQUWBX-UHFFFAOYSA-N 0.000 description 1
- ZZLQGKUTUGIQNL-UHFFFAOYSA-N 7-methyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(C)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 ZZLQGKUTUGIQNL-UHFFFAOYSA-N 0.000 description 1
- YZIDHIOWIUILEQ-UHFFFAOYSA-N 7-methylsulfanyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(SC)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 YZIDHIOWIUILEQ-UHFFFAOYSA-N 0.000 description 1
- PSRFZVMHJDITLA-UHFFFAOYSA-N 7-methylsulfinyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC([S+]([O-])C)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 PSRFZVMHJDITLA-UHFFFAOYSA-N 0.000 description 1
- RXCDCVYRSFPGHQ-UHFFFAOYSA-N 7-methylsulfonyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(S(=O)(=O)C)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 RXCDCVYRSFPGHQ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZQNMREXZDXVUPB-UHFFFAOYSA-N 8-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C=1C(Cl)=CC=C2C=1NC(=O)CN=C2C1=CC=CC=C1 ZQNMREXZDXVUPB-UHFFFAOYSA-N 0.000 description 1
- OGDLFFYXUKTNDD-UHFFFAOYSA-N 8-methoxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C=1C(OC)=CC=C2C=1NC(=O)CN=C2C1=CC=CC=C1 OGDLFFYXUKTNDD-UHFFFAOYSA-N 0.000 description 1
- NOJVFPSKPFOJHX-UHFFFAOYSA-N 8-nitro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C=1C([N+](=O)[O-])=CC=C2C=1NC(=O)CN=C2C1=CC=CC=C1 NOJVFPSKPFOJHX-UHFFFAOYSA-N 0.000 description 1
- NUXRLDCCKDXYCK-UHFFFAOYSA-N 9-chloro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound ClC1=CC=CC2=C1NC(=O)CN=C2C1=CC=CC=C1 NUXRLDCCKDXYCK-UHFFFAOYSA-N 0.000 description 1
- YYSSSENOSHKUEM-UHFFFAOYSA-N 9-nitro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound [O-][N+](=O)C1=CC=CC2=C1NC(=O)CN=C2C1=CC=CC=C1 YYSSSENOSHKUEM-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YMDCXLFARNYMJK-UHFFFAOYSA-N Cl.C(C)SC=1C=CC2=C(C(=NCC(N2)=O)C2=CC=CC=C2)C1 Chemical compound Cl.C(C)SC=1C=CC2=C(C(=NCC(N2)=O)C2=CC=CC=C2)C1 YMDCXLFARNYMJK-UHFFFAOYSA-N 0.000 description 1
- XFWIVWMJNHCZJY-UHFFFAOYSA-N Cl.C(CCC)SC=1C=CC2=C(C(=NCC(N2)=O)C2=CC=CC=C2)C1 Chemical compound Cl.C(CCC)SC=1C=CC2=C(C(=NCC(N2)=O)C2=CC=CC=C2)C1 XFWIVWMJNHCZJY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- YLCXGBZIZBEVPZ-UHFFFAOYSA-N Medazepam Chemical compound C12=CC(Cl)=CC=C2N(C)CCN=C1C1=CC=CC=C1 YLCXGBZIZBEVPZ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- WPNMLCMTDCANOZ-UHFFFAOYSA-N [5-chloro-2-(methylamino)phenyl]-phenylmethanone Chemical compound CNC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 WPNMLCMTDCANOZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 229960003965 antiepileptics Drugs 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- IKWQWOFXRCUIFT-UHFFFAOYSA-N benzene-1,2-dicarbohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C(=O)NN IKWQWOFXRCUIFT-UHFFFAOYSA-N 0.000 description 1
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 description 1
- 150000001557 benzodiazepines Chemical class 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- VAVRLZSOYQZLMB-UHFFFAOYSA-N benzyl n-aminocarbamate;hydrochloride Chemical compound Cl.NNC(=O)OCC1=CC=CC=C1 VAVRLZSOYQZLMB-UHFFFAOYSA-N 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- CHIFCDOIPRCHCF-UHFFFAOYSA-N delorazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)CN=C1C1=CC=CC=C1Cl CHIFCDOIPRCHCF-UHFFFAOYSA-N 0.000 description 1
- UVCOILFBWYKHHB-UHFFFAOYSA-N desalkylflurazepam Chemical compound FC1=CC=CC=C1C1=NCC(=O)NC2=CC=C(Cl)C=C12 UVCOILFBWYKHHB-UHFFFAOYSA-N 0.000 description 1
- VPAYQWRBBOGGPY-UHFFFAOYSA-N diclazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl VPAYQWRBBOGGPY-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ZRKDDZBVSZLOFS-UHFFFAOYSA-N flubromazepam Chemical compound FC1=CC=CC=C1C1=NCC(=O)NC2=CC=C(Br)C=C12 ZRKDDZBVSZLOFS-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- GWUSZQUVEVMBPI-UHFFFAOYSA-N nimetazepam Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 GWUSZQUVEVMBPI-UHFFFAOYSA-N 0.000 description 1
- KJONHKAYOJNZEC-UHFFFAOYSA-N nitrazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1 KJONHKAYOJNZEC-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- AKPLHCDWDRPJGD-UHFFFAOYSA-N nordazepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 AKPLHCDWDRPJGD-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000005544 phthalimido group Chemical group 0.000 description 1
- 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- UUBMOUNXQFMBQF-UHFFFAOYSA-N ro5-2904 Chemical compound C12=CC(C(F)(F)F)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 UUBMOUNXQFMBQF-UHFFFAOYSA-N 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP688468A JPS5130074B1 (enExample) | 1968-02-06 | 1968-02-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH513886A true CH513886A (de) | 1971-10-15 |
Family
ID=11650643
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH115269A CH513886A (de) | 1968-02-06 | 1969-01-23 | Verfahren zur Herstellung von Benzodiazepin-Derivaten |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS5130074B1 (enExample) |
| BR (1) | BR6906070D0 (enExample) |
| CH (1) | CH513886A (enExample) |
| DK (1) | DK136423C (enExample) |
| ES (1) | ES363295A1 (enExample) |
| SE (1) | SE372532B (enExample) |
| YU (1) | YU33789B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2132708A1 (enExample) * | 1971-04-08 | 1972-11-24 | Chugai Pharmaceutical Co Ltd |
-
1968
- 1968-02-06 JP JP688468A patent/JPS5130074B1/ja active Pending
-
1969
- 1969-01-23 CH CH115269A patent/CH513886A/de not_active IP Right Cessation
- 1969-01-28 SE SE112569A patent/SE372532B/xx unknown
- 1969-02-03 BR BR20607069A patent/BR6906070D0/pt unknown
- 1969-02-04 DK DK60369A patent/DK136423C/da not_active IP Right Cessation
- 1969-02-05 ES ES363295A patent/ES363295A1/es not_active Expired
- 1969-02-06 YU YU27169A patent/YU33789B/xx unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2132708A1 (enExample) * | 1971-04-08 | 1972-11-24 | Chugai Pharmaceutical Co Ltd |
Also Published As
| Publication number | Publication date |
|---|---|
| BR6906070D0 (pt) | 1973-03-13 |
| YU27169A (en) | 1977-10-31 |
| YU33789B (en) | 1978-05-15 |
| DK136423B (da) | 1977-10-10 |
| SE372532B (enExample) | 1974-12-23 |
| DK136423C (da) | 1978-03-13 |
| ES363295A1 (es) | 1970-12-16 |
| JPS5130074B1 (enExample) | 1976-08-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |