DE1288610B - Verfahren zur Herstellung von 2-Oxo-1, 2-dihydro-3H-1, 4-benzodiazepinen - Google Patents
Verfahren zur Herstellung von 2-Oxo-1, 2-dihydro-3H-1, 4-benzodiazepinenInfo
- Publication number
- DE1288610B DE1288610B DEH41139A DEH0041139A DE1288610B DE 1288610 B DE1288610 B DE 1288610B DE H41139 A DEH41139 A DE H41139A DE H0041139 A DEH0041139 A DE H0041139A DE 1288610 B DE1288610 B DE 1288610B
- Authority
- DE
- Germany
- Prior art keywords
- oxo
- dihydro
- molecular weight
- benzodiazepine
- low molecular
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 6
- UDLAUVFRZXIQJS-UHFFFAOYSA-N 1,3-dihydro-1,4-benzodiazepin-2-one Chemical class N1C(=O)CN=CC2=CC=CC=C21 UDLAUVFRZXIQJS-UHFFFAOYSA-N 0.000 title claims 2
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000007795 chemical reaction product Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- -1 phosphorus halide Chemical class 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- 239000011574 phosphorus Substances 0.000 claims description 3
- 229910052698 phosphorus Inorganic materials 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 150000001557 benzodiazepines Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000002844 melting Methods 0.000 description 59
- 230000008018 melting Effects 0.000 description 59
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- QQUIWIVTEWQHKA-UHFFFAOYSA-N 3h-1,4-benzodiazepine Chemical compound C1=NCC=NC2=CC=CC=C21 QQUIWIVTEWQHKA-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 239000007868 Raney catalyst Substances 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- NBMRAXVZMPSMQF-UHFFFAOYSA-N N1CC[N+](=CC2=C1C=CC=C2)[O-] Chemical compound N1CC[N+](=CC2=C1C=CC=C2)[O-] NBMRAXVZMPSMQF-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
- 239000002253 acid Substances 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- GGRWZBVSUZZMKS-UHFFFAOYSA-N demoxepam Chemical compound C12=CC(Cl)=CC=C2NC(=O)C[N+]([O-])=C1C1=CC=CC=C1 GGRWZBVSUZZMKS-UHFFFAOYSA-N 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- OEGHKMSYOJOVNJ-UHFFFAOYSA-N 4-oxido-3H-1,4-benzodiazepin-4-ium Chemical compound N1=CC[N+](=CC2=C1C=CC=C2)[O-] OEGHKMSYOJOVNJ-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- XQPHRSXQZMGKHF-UHFFFAOYSA-N N1C(C[N+](=CC2=C1C=CC=C2)[O-])=O Chemical compound N1C(C[N+](=CC2=C1C=CC=C2)[O-])=O XQPHRSXQZMGKHF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000004323 potassium nitrate Substances 0.000 description 2
- 235000010333 potassium nitrate Nutrition 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- QNRATNLHPGXHMA-XZHTYLCXSA-N (r)-(6-ethoxyquinolin-4-yl)-[(2s,4s,5r)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl]methanol;hydrochloride Chemical compound Cl.C([C@H]([C@H](C1)CC)C2)CN1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OCC)C=C21 QNRATNLHPGXHMA-XZHTYLCXSA-N 0.000 description 1
- NSGCECVNIHAAIE-UHFFFAOYSA-N 2,3-dihydro-1h-1,4-benzodiazepine Chemical compound N1CCN=CC2=CC=CC=C21 NSGCECVNIHAAIE-UHFFFAOYSA-N 0.000 description 1
- VKTTYIXIDXWHKW-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)aniline Chemical compound NC1=CC(C(F)(F)F)=CC=C1Cl VKTTYIXIDXWHKW-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- PRMIWZTXQDCXCT-UHFFFAOYSA-N 3-methyl-7-nitro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC([N+]([O-])=O)=CC=C2NC(=O)C(C)N=C1C1=CC=CC=C1 PRMIWZTXQDCXCT-UHFFFAOYSA-N 0.000 description 1
- KVBZGDNWBRCXHF-UHFFFAOYSA-N 3-oxidoquinazolin-3-ium Chemical compound C1=CC=CC2=C[N+]([O-])=CN=C21 KVBZGDNWBRCXHF-UHFFFAOYSA-N 0.000 description 1
- OJISXAOTBSUAOL-UHFFFAOYSA-N 5-(2-chlorophenyl)-7,8-dimethyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C1=2C=C(C)C(C)=CC=2NC(=O)CN=C1C1=CC=CC=C1Cl OJISXAOTBSUAOL-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
- DWKRKWLFPIBTHA-UHFFFAOYSA-N 5-phenyl-7-(trifluoromethyl)-3H-1,4-benzodiazepine Chemical compound C1(=CC=CC=C1)C1=NCC=NC2=C1C=C(C=C2)C(F)(F)F DWKRKWLFPIBTHA-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
- ZMXLAUDJKIBNLG-UHFFFAOYSA-N 7,9-dimethyl-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(C)=CC(C)=C2NC(=O)CN=C1C1=CC=CC=C1 ZMXLAUDJKIBNLG-UHFFFAOYSA-N 0.000 description 1
- KMADJPBGARDOAO-UHFFFAOYSA-N 7-bromo-5-(2-fluorophenyl)-1-methyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(C)C2=CC=C(Br)C=C2C=1C1=CC=CC=C1F KMADJPBGARDOAO-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
- ATCCWKYKHCKDGT-UHFFFAOYSA-N 7-bromo-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C12=CC(Br)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 ATCCWKYKHCKDGT-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
- 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
- BUCORZSTKDOEKQ-UHFFFAOYSA-N 7-chloro-4-hydroxy-N-methyl-5-phenyl-3H-1,4-benzodiazepin-2-imine Chemical compound C=12C=C(Cl)C=CC2=NC(=NC)CN(O)C=1C1=CC=CC=C1 BUCORZSTKDOEKQ-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
- LUHWKYPQVCYWDV-UHFFFAOYSA-N 7-chloro-5-(3-chlorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound ClC1=CC=CC(C=2C3=CC(Cl)=CC=C3NC(=O)CN=2)=C1 LUHWKYPQVCYWDV-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
- 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
- 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
- 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 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
- CTIOCCLJDVAGLD-UHFFFAOYSA-N ClC1=C(C(C2=CC=CC=C2)=N)C=C(C=C1)C(F)(F)F Chemical compound ClC1=C(C(C2=CC=CC=C2)=N)C=C(C=C1)C(F)(F)F CTIOCCLJDVAGLD-UHFFFAOYSA-N 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- AVPYVFOHLZKIET-UHFFFAOYSA-N N-[[2-amino-5-(trifluoromethyl)phenyl]-phenylmethylidene]hydroxylamine Chemical compound NC1=C(C(C2=CC=CC=C2)=NO)C=C(C=C1)C(F)(F)F AVPYVFOHLZKIET-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 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 1
- QHDJJBSLUFDASY-UHFFFAOYSA-N [2-chloro-5-(trifluoromethyl)phenyl]-phenylmethanone Chemical compound FC(F)(F)C1=CC=C(Cl)C(C(=O)C=2C=CC=CC=2)=C1 QHDJJBSLUFDASY-UHFFFAOYSA-N 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 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
- 150000001768 cations Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940045803 cuprous chloride Drugs 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
- 238000007865 diluting Methods 0.000 description 1
- 238000001035 drying Methods 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
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 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
- 239000000463 material Substances 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- HXTHYOABCQCIOL-UHFFFAOYSA-N n-(7-chloro-4-oxido-5-phenyl-3h-1,4-benzodiazepin-4-ium-2-yl)-n-methylacetamide Chemical compound [O-][N+]=1CC(N(C(C)=O)C)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 HXTHYOABCQCIOL-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
- 150000002825 nitriles Chemical class 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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000002244 precipitate Substances 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
- 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
- 150000003839 salts Chemical class 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 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
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/42—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrolysis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
- C07C49/16—Saturated compounds containing keto groups bound to acyclic carbon atoms containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/80—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen
- C07C49/813—Ketones containing a keto group bound to a six-membered aromatic ring containing halogen polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/20—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms
- C07D243/26—Preparation from compounds already containing the benzodiazepine skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85856459A | 1959-12-10 | 1959-12-10 | |
| US260560A | 1960-01-15 | 1960-01-15 | |
| US2468660A | 1960-04-26 | 1960-04-26 | |
| US3873260A | 1960-06-27 | 1960-06-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1288610B true DE1288610B (de) | 1969-02-06 |
Family
ID=27485190
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH41138A Pending DE1290143B (de) | 1959-12-10 | 1960-12-07 | 2-Oxo-1, 2-dihydro-3H-1, 4-benzodiazepinderivate |
| DEH41139A Pending DE1288610B (de) | 1959-12-10 | 1960-12-07 | Verfahren zur Herstellung von 2-Oxo-1, 2-dihydro-3H-1, 4-benzodiazepinen |
| DEH41137A Pending DE1288609B (de) | 1959-12-10 | 1960-12-07 | 2-Oxo-1, 2-dihydro-3H-1, 4-benzodiazepine |
| DE19601445073 Pending DE1445073A1 (de) | 1959-12-10 | 1960-12-19 | Verfahren zur Herstellung von fluorhaltigen Benzodiazepin-Derivaten |
| DE19641445908 Pending DE1445908A1 (de) | 1959-12-10 | 1964-09-10 | Verfahren zur Herstellung von 1,4-Benzodiazepin-Derivaten |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH41138A Pending DE1290143B (de) | 1959-12-10 | 1960-12-07 | 2-Oxo-1, 2-dihydro-3H-1, 4-benzodiazepinderivate |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH41137A Pending DE1288609B (de) | 1959-12-10 | 1960-12-07 | 2-Oxo-1, 2-dihydro-3H-1, 4-benzodiazepine |
| DE19601445073 Pending DE1445073A1 (de) | 1959-12-10 | 1960-12-19 | Verfahren zur Herstellung von fluorhaltigen Benzodiazepin-Derivaten |
| DE19641445908 Pending DE1445908A1 (de) | 1959-12-10 | 1964-09-10 | Verfahren zur Herstellung von 1,4-Benzodiazepin-Derivaten |
Country Status (11)
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1295563B (de) * | 1963-05-29 | 1969-05-22 | American Home Prod | Verfahren zur Herstellung von 5-Phenyl-7-chlor-1, 2-dihydro-3H-1, 4-benzodiazepinon-(2)-4-oxyd |
| GB1333501A (en) * | 1971-03-05 | 1973-10-10 | Ravizza Spa | Process for the preparation of 7-chlorobenzodiazepine de rivatives |
| US4820834A (en) * | 1984-06-26 | 1989-04-11 | Merck & Co., Inc. | Benzodiazepine analogs |
| CA1332410C (en) * | 1984-06-26 | 1994-10-11 | Roger M. Freidinger | Benzodiazepine analogs |
| AU2002317910B2 (en) | 2001-06-07 | 2008-06-19 | Via Pharmaceuticals, Inc. | Cyclic nucleotide phosphodiesterase inhibitors, preparation and uses thereof |
| MXPA04011465A (es) * | 2002-05-24 | 2005-02-14 | Millennium Pharm Inc | Inhibidores de ccr9 y metodos de uso de los mismos. |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2893992A (en) * | 1959-07-07 | I ii i i |
-
1960
- 1960-12-02 CH CH1349060A patent/CH411910A/de unknown
- 1960-12-02 CH CH1349160A patent/CH408029A/de unknown
- 1960-12-02 CH CH1349360A patent/CH418342A/de unknown
- 1960-12-02 CH CH1348960A patent/CH408940A/de unknown
- 1960-12-02 CH CH1349460A patent/CH414652A/de unknown
- 1960-12-02 CH CH1230565A patent/CH408045A/de unknown
- 1960-12-02 CH CH1349260A patent/CH418341A/de unknown
- 1960-12-02 CH CH1349560A patent/CH414653A/de unknown
- 1960-12-07 DE DEH41138A patent/DE1290143B/de active Pending
- 1960-12-07 BR BR124755/60A patent/BR6024755D0/pt unknown
- 1960-12-07 DE DEH41139A patent/DE1288610B/de active Pending
- 1960-12-07 DE DEH41137A patent/DE1288609B/de active Pending
- 1960-12-09 GB GB42400/60A patent/GB972962A/en not_active Expired
- 1960-12-09 BE BE598012A patent/BE598012A/fr unknown
- 1960-12-09 ES ES0263123A patent/ES263123A1/es not_active Expired
- 1960-12-09 GB GB40979/62A patent/GB972973A/en not_active Expired
- 1960-12-09 GB GB40978/62A patent/GB972972A/en not_active Expired
- 1960-12-09 GB GB42399/60A patent/GB972961A/en not_active Expired
- 1960-12-09 BE BE598008A patent/BE598008A/fr unknown
- 1960-12-09 GB GB20071/63A patent/GB972976A/en not_active Expired
- 1960-12-09 GB GB42403/60A patent/GB972965A/en not_active Expired
- 1960-12-09 GB GB42401/60A patent/GB972963A/en not_active Expired
- 1960-12-09 GB GB42405/60A patent/GB972967A/en not_active Expired
- 1960-12-09 GB GB42408/60A patent/GB972968A/en not_active Expired
- 1960-12-09 ES ES0263124A patent/ES263124A1/es not_active Expired
- 1960-12-09 GB GB42404/60A patent/GB972966A/en not_active Expired
- 1960-12-09 BE BE598015A patent/BE598015A/fr unknown
- 1960-12-09 BE BE598013A patent/BE598013A/fr unknown
- 1960-12-09 GB GB42402/60A patent/GB972964A/en not_active Expired
- 1960-12-13 CH CH1389960A patent/CH396016A/de unknown
- 1960-12-19 DE DE19601445073 patent/DE1445073A1/de active Pending
-
1961
- 1961-01-11 GB GB1168/61A patent/GB972969A/en not_active Expired
- 1961-01-11 GB GB29834/62A patent/GB972970A/en not_active Expired
-
1964
- 1964-09-10 DE DE19641445908 patent/DE1445908A1/de active Pending
- 1964-10-21 NL NL6412251A patent/NL6412251A/xx unknown
- 1964-10-21 NL NL6412250A patent/NL6412250A/xx unknown
- 1964-12-16 OA OA50896A patent/OA00817A/xx unknown
- 1964-12-16 OA OA50895A patent/OA00816A/xx unknown
- 1964-12-26 OA OA51048A patent/OA00953A/xx unknown
- 1964-12-26 OA OA51054A patent/OA00959A/xx unknown
- 1964-12-26 OA OA51053A patent/OA00958A/xx unknown
-
1965
- 1965-09-17 SE SE12149/65A patent/SE310887B/xx unknown
- 1965-11-03 CY CY32465A patent/CY324A/xx unknown
- 1965-12-31 MY MY1965178A patent/MY6500178A/xx unknown
-
1967
- 1967-03-30 OA OA52849A patent/OA02384A/xx unknown
- 1967-03-30 OA OA52850A patent/OA02385A/xx unknown
- 1967-11-15 SE SE1570567A patent/SE318283B/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2893992A (en) * | 1959-07-07 | I ii i i |
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