CH578545A5 - Cns-active 1-subst 1,4-benzodiazepin-2-ones - Google Patents
Cns-active 1-subst 1,4-benzodiazepin-2-onesInfo
- Publication number
- CH578545A5 CH578545A5 CH104576A CH104576A CH578545A5 CH 578545 A5 CH578545 A5 CH 578545A5 CH 104576 A CH104576 A CH 104576A CH 104576 A CH104576 A CH 104576A CH 578545 A5 CH578545 A5 CH 578545A5
- Authority
- CH
- Switzerland
- Prior art keywords
- benzodiazepin
- dihydro
- chloro
- acid
- phenyl
- Prior art date
Links
- RGGLEJFUEMKQSH-UHFFFAOYSA-N 1,4-benzodiazepin-2-one Chemical class O=C1C=NC=C2C=CC=CC2=N1 RGGLEJFUEMKQSH-UHFFFAOYSA-N 0.000 title abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 239000002904 solvent Substances 0.000 claims description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
- 229940049706 benzodiazepine Drugs 0.000 claims description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 4
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229910017604 nitric acid Inorganic materials 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 2
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 claims description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 2
- KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 235000019253 formic acid Nutrition 0.000 claims description 2
- AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims description 2
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 229910001927 ruthenium tetroxide Inorganic materials 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 claims 1
- 150000002148 esters Chemical class 0.000 abstract description 6
- 239000003158 myorelaxant agent Substances 0.000 abstract description 5
- 239000000932 sedative agent Substances 0.000 abstract description 4
- 239000001961 anticonvulsive agent Substances 0.000 abstract description 3
- 230000000147 hypnotic effect Effects 0.000 abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 230000001773 anti-convulsant effect Effects 0.000 abstract 1
- 229960003965 antiepileptics Drugs 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- -1 antispasmodics Substances 0.000 description 18
- 239000000203 mixture Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 150000001557 benzodiazepines Chemical class 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 229940035363 muscle relaxants Drugs 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- ARAFEULRMHFMDE-UHFFFAOYSA-N 1,3-oxazolidine-2,5-dione Chemical compound O=C1CNC(=O)O1 ARAFEULRMHFMDE-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 3
- ILVCYLJLDTWAAW-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-1-(ethylsulfonylmethyl)-3H-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)(=O)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl ILVCYLJLDTWAAW-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000009835 boiling Methods 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
- 239000000155 melt Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229940125723 sedative agent Drugs 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- 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 2
- NSFQYFCTDWFNSC-UHFFFAOYSA-N 1-(ethylsulfonylmethyl)-7-nitro-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)(=O)CC)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 NSFQYFCTDWFNSC-UHFFFAOYSA-N 0.000 description 2
- DYENXVJTSGQOPR-UHFFFAOYSA-N 7-chloro-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound N1C(=O)CN=CC2=CC(Cl)=CC=C21 DYENXVJTSGQOPR-UHFFFAOYSA-N 0.000 description 2
- BFSKMWCXYBODSI-UHFFFAOYSA-N 7-chloro-1-(methylsulfonylmethyl)-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)(=O)C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 BFSKMWCXYBODSI-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 229940125681 anticonvulsant agent Drugs 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 239000003326 hypnotic agent Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000003791 organic solvent mixture Substances 0.000 description 2
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003204 tranquilizing agent Substances 0.000 description 2
- 230000002936 tranquilizing effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 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 1
- MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 1
- MLIWQXBKMZNZNF-KUHOPJCQSA-N (2e)-2,6-bis[(4-azidophenyl)methylidene]-4-methylcyclohexan-1-one Chemical compound O=C1\C(=C\C=2C=CC(=CC=2)N=[N+]=[N-])CC(C)CC1=CC1=CC=C(N=[N+]=[N-])C=C1 MLIWQXBKMZNZNF-KUHOPJCQSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- HOICSGJPACIQQP-UHFFFAOYSA-N 1-(3-ethylsulfinylpropyl)-7-nitro-5-phenyl-3H-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)CC)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 HOICSGJPACIQQP-UHFFFAOYSA-N 0.000 description 1
- GYAAZAGXSUGSLP-UHFFFAOYSA-N 1-(3-ethylsulfonylpropyl)-5-phenyl-7-(trifluoromethyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)(=O)CC)C2=CC=C(C(F)(F)F)C=C2C=1C1=CC=CC=C1 GYAAZAGXSUGSLP-UHFFFAOYSA-N 0.000 description 1
- URGLBYWEUNIHBY-UHFFFAOYSA-N 1-(3-ethylsulfonylpropyl)-7-nitro-5-phenyl-3H-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)(=O)CC)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 URGLBYWEUNIHBY-UHFFFAOYSA-N 0.000 description 1
- MUANBEQXKCJEQG-UHFFFAOYSA-N 1-(3-methylsulfinylpropyl)-5-phenyl-7-(trifluoromethyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)C)C2=CC=C(C(F)(F)F)C=C2C=1C1=CC=CC=C1 MUANBEQXKCJEQG-UHFFFAOYSA-N 0.000 description 1
- QEWYQZGERSZOKT-UHFFFAOYSA-N 1-(3-methylsulfinylpropyl)-7-nitro-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 QEWYQZGERSZOKT-UHFFFAOYSA-N 0.000 description 1
- YYRDIWHWJLNFKX-UHFFFAOYSA-N 1-(3-methylsulfonylpropyl)-7-nitro-5-phenyl-3H-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)(=O)C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 YYRDIWHWJLNFKX-UHFFFAOYSA-N 0.000 description 1
- CGSBBTJPJDTNDC-UHFFFAOYSA-N 1-(ethylsulfinylmethyl)-2-oxo-5-phenyl-3H-1,4-benzodiazepine-7-carbonitrile Chemical compound N=1CC(=O)N(CS(=O)CC)C2=CC=C(C#N)C=C2C=1C1=CC=CC=C1 CGSBBTJPJDTNDC-UHFFFAOYSA-N 0.000 description 1
- JRLWDTBPXAZQNE-UHFFFAOYSA-N 1-(ethylsulfinylmethyl)-5-phenyl-7-(trifluoromethyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)CC)C2=CC=C(C(F)(F)F)C=C2C=1C1=CC=CC=C1 JRLWDTBPXAZQNE-UHFFFAOYSA-N 0.000 description 1
- GBLRJCFLJNPXMO-UHFFFAOYSA-N 1-(ethylsulfinylmethyl)-7-nitro-5-phenyl-3H-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)CC)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 GBLRJCFLJNPXMO-UHFFFAOYSA-N 0.000 description 1
- AWORSZWOJZQUSG-UHFFFAOYSA-N 1-(ethylsulfonylmethyl)-2-oxo-5-phenyl-3H-1,4-benzodiazepine-7-carbonitrile Chemical compound N=1CC(=O)N(CS(=O)(=O)CC)C2=CC=C(C#N)C=C2C=1C1=CC=CC=C1 AWORSZWOJZQUSG-UHFFFAOYSA-N 0.000 description 1
- UVBADRDOORKJOU-UHFFFAOYSA-N 1-(ethylsulfonylmethyl)-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)(=O)CC)C2=CC=CC=C2C=1C1=CC=CC=C1 UVBADRDOORKJOU-UHFFFAOYSA-N 0.000 description 1
- UVJQWKDFFWFCGI-UHFFFAOYSA-N 1-(ethylsulfonylmethyl)-5-phenyl-7-(trifluoromethyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)(=O)CC)C2=CC=C(C(F)(F)F)C=C2C=1C1=CC=CC=C1 UVJQWKDFFWFCGI-UHFFFAOYSA-N 0.000 description 1
- BEDGIVTVMSYHRO-UHFFFAOYSA-N 1-(methylsulfinylmethyl)-2-oxo-5-phenyl-3h-1,4-benzodiazepine-7-carbonitrile Chemical compound N=1CC(=O)N(CS(=O)C)C2=CC=C(C#N)C=C2C=1C1=CC=CC=C1 BEDGIVTVMSYHRO-UHFFFAOYSA-N 0.000 description 1
- WJYXMFSAHFWRCA-UHFFFAOYSA-N 1-(methylsulfinylmethyl)-7-nitro-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 WJYXMFSAHFWRCA-UHFFFAOYSA-N 0.000 description 1
- TZGUCHAAEAZCEU-UHFFFAOYSA-N 1-(methylsulfonylmethyl)-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)(=O)C)C2=CC=CC=C2C=1C1=CC=CC=C1 TZGUCHAAEAZCEU-UHFFFAOYSA-N 0.000 description 1
- GWZZULOJOBLXGM-UHFFFAOYSA-N 1-(methylsulfonylmethyl)-7-nitro-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)(=O)C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 GWZZULOJOBLXGM-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- VVDRVODULUWWTE-UHFFFAOYSA-N 5-(2-chlorophenyl)-1-(3-ethylsulfinylpropyl)-7-nitro-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)CC)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1Cl VVDRVODULUWWTE-UHFFFAOYSA-N 0.000 description 1
- NUPPVCQMUXQBEN-UHFFFAOYSA-N 5-(2-chlorophenyl)-1-(3-ethylsulfonylpropyl)-7-nitro-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)(=O)CC)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1Cl NUPPVCQMUXQBEN-UHFFFAOYSA-N 0.000 description 1
- DPUPSYGDEKWHMT-UHFFFAOYSA-N 5-(2-chlorophenyl)-1-(3-methylsulfinylpropyl)-7-nitro-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1Cl DPUPSYGDEKWHMT-UHFFFAOYSA-N 0.000 description 1
- CFENNAQEDDOLBM-UHFFFAOYSA-N 5-(2-chlorophenyl)-7-nitro-1-(propylsulfinylmethyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)CCC)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1Cl CFENNAQEDDOLBM-UHFFFAOYSA-N 0.000 description 1
- OJTNUVKIKHKGJS-UHFFFAOYSA-N 7-bromo-1-(3-ethylsulfinylpropyl)-5-phenyl-3H-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)CC)C2=CC=C(Br)C=C2C=1C1=CC=CC=C1 OJTNUVKIKHKGJS-UHFFFAOYSA-N 0.000 description 1
- OKNMPYWGPOGYPB-UHFFFAOYSA-N 7-bromo-1-(3-ethylsulfonylpropyl)-5-phenyl-3H-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)(=O)CC)C2=CC=C(Br)C=C2C=1C1=CC=CC=C1 OKNMPYWGPOGYPB-UHFFFAOYSA-N 0.000 description 1
- XLMWORGXTQKTDZ-UHFFFAOYSA-N 7-bromo-1-(ethylsulfinylmethyl)-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)CC)C2=CC=C(Br)C=C2C=1C1=CC=CC=C1 XLMWORGXTQKTDZ-UHFFFAOYSA-N 0.000 description 1
- KQXDMFYDHQBJFB-UHFFFAOYSA-N 7-bromo-1-(ethylsulfonylmethyl)-5-phenyl-3H-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)(=O)CC)C2=CC=C(Br)C=C2C=1C1=CC=CC=C1 KQXDMFYDHQBJFB-UHFFFAOYSA-N 0.000 description 1
- CNDNANRMBUIUER-UHFFFAOYSA-N 7-bromo-1-(methylsulfinylmethyl)-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)C)C2=CC=C(Br)C=C2C=1C1=CC=CC=C1 CNDNANRMBUIUER-UHFFFAOYSA-N 0.000 description 1
- FJOYRFBNFLWDOT-UHFFFAOYSA-N 7-chloro-1-(2-methylsulfinylethyl)-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCS(=O)C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 FJOYRFBNFLWDOT-UHFFFAOYSA-N 0.000 description 1
- CVOQPERREXIWAH-UHFFFAOYSA-N 7-chloro-1-(2-methylsulfonylethyl)-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCS(=O)(=O)C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 CVOQPERREXIWAH-UHFFFAOYSA-N 0.000 description 1
- MHWCQJZBDYGHIB-UHFFFAOYSA-N 7-chloro-1-(3-ethylsulfinylpropyl)-5-(2-fluorophenyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F MHWCQJZBDYGHIB-UHFFFAOYSA-N 0.000 description 1
- YUWJMDTVDFLILO-UHFFFAOYSA-N 7-chloro-1-(3-ethylsulfinylpropyl)-5-(2-methylphenyl)-3H-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1C YUWJMDTVDFLILO-UHFFFAOYSA-N 0.000 description 1
- UYIRRJCXWOAMCX-UHFFFAOYSA-N 7-chloro-1-(3-ethylsulfonylpropyl)-5-(2-fluorophenyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)(=O)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F UYIRRJCXWOAMCX-UHFFFAOYSA-N 0.000 description 1
- YZUOOXGXIIZCAN-UHFFFAOYSA-N 7-chloro-1-(3-ethylsulfonylpropyl)-5-[2-(trifluoromethyl)phenyl]-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)(=O)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1C(F)(F)F YZUOOXGXIIZCAN-UHFFFAOYSA-N 0.000 description 1
- RBJVBDTZICHOCA-UHFFFAOYSA-N 7-chloro-1-(3-ethylsulfonylpropyl)-5-phenyl-3H-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)(=O)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 RBJVBDTZICHOCA-UHFFFAOYSA-N 0.000 description 1
- GFURDBIDBRBPIW-UHFFFAOYSA-N 7-chloro-1-(3-methylsulfinylpropyl)-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 GFURDBIDBRBPIW-UHFFFAOYSA-N 0.000 description 1
- NRBAHEZLDIPLLB-UHFFFAOYSA-N 7-chloro-1-(3-methylsulfonylpropyl)-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)(=O)C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 NRBAHEZLDIPLLB-UHFFFAOYSA-N 0.000 description 1
- DWGREBFUYKQYLO-UHFFFAOYSA-N 7-chloro-1-(ethylsulfinylmethyl)-5-(2-fluorophenyl)-3H-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F DWGREBFUYKQYLO-UHFFFAOYSA-N 0.000 description 1
- UFEFFKZBNBKIMM-UHFFFAOYSA-N 7-chloro-1-(ethylsulfinylmethyl)-5-[2-(trifluoromethyl)phenyl]-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1C(F)(F)F UFEFFKZBNBKIMM-UHFFFAOYSA-N 0.000 description 1
- CGYGHQWJYKBCNF-UHFFFAOYSA-N 7-chloro-1-(ethylsulfonylmethyl)-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)(=O)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 CGYGHQWJYKBCNF-UHFFFAOYSA-N 0.000 description 1
- JZKVAWLTIJFXQC-UHFFFAOYSA-N 7-chloro-1-(propylsulfonylmethyl)-5-[2-(trifluoromethyl)phenyl]-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)(=O)CCC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1C(F)(F)F JZKVAWLTIJFXQC-UHFFFAOYSA-N 0.000 description 1
- SAKRRBRUBXSBKD-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-1-(3-ethylsulfinylpropyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl SAKRRBRUBXSBKD-UHFFFAOYSA-N 0.000 description 1
- OUWOOFBUMYYYDC-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-1-(3-ethylsulfonylpropyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)(=O)CC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl OUWOOFBUMYYYDC-UHFFFAOYSA-N 0.000 description 1
- MSGXAKHJPJOMOK-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-1-(3-methylsulfonylpropyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)(=O)C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl MSGXAKHJPJOMOK-UHFFFAOYSA-N 0.000 description 1
- NJZQRLHMKHSIEX-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-1-(methylsulfinylmethyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl NJZQRLHMKHSIEX-UHFFFAOYSA-N 0.000 description 1
- PEONULQHAQSDLP-UHFFFAOYSA-N 7-chloro-5-(2-chlorophenyl)-1-(propylsulfinylmethyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)CCC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1Cl PEONULQHAQSDLP-UHFFFAOYSA-N 0.000 description 1
- JHSVIYYVRLIPDK-UHFFFAOYSA-N 7-chloro-5-(2-fluorophenyl)-1-(2-methylsulfonylethyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCS(=O)(=O)C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F JHSVIYYVRLIPDK-UHFFFAOYSA-N 0.000 description 1
- HMBFLAWETXSAEL-UHFFFAOYSA-N 7-chloro-5-(2-fluorophenyl)-1-(3-methylsulfinylpropyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F HMBFLAWETXSAEL-UHFFFAOYSA-N 0.000 description 1
- GXOUUFZTWIDOKI-UHFFFAOYSA-N 7-chloro-5-(2-fluorophenyl)-1-(3-methylsulfonylpropyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CCCS(=O)(=O)C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F GXOUUFZTWIDOKI-UHFFFAOYSA-N 0.000 description 1
- AQTJXDXZDPRBDO-UHFFFAOYSA-N 7-chloro-5-(2-fluorophenyl)-1-(methylsulfinylmethyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F AQTJXDXZDPRBDO-UHFFFAOYSA-N 0.000 description 1
- JDROOALFTLFCLT-UHFFFAOYSA-N 7-chloro-5-(2-fluorophenyl)-1-(methylsulfonylmethyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)(=O)C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F JDROOALFTLFCLT-UHFFFAOYSA-N 0.000 description 1
- OFEBJEWVGRFXBR-UHFFFAOYSA-N 7-chloro-5-(2-methylphenyl)-1-(3-methylsulfinylpropyl)-3h-1,4-benzodiazepin-2-one Chemical compound CC1=CC=CC=C1C1=NCC(=O)N(CCCS(C)=O)C2=CC=C(Cl)C=C12 OFEBJEWVGRFXBR-UHFFFAOYSA-N 0.000 description 1
- YQDFEIOLHIWUKV-UHFFFAOYSA-N 7-chloro-5-(2-methylphenyl)-1-(3-methylsulfonylpropyl)-3h-1,4-benzodiazepin-2-one Chemical compound CC1=CC=CC=C1C1=NCC(=O)N(CCCS(C)(=O)=O)C2=CC=C(Cl)C=C12 YQDFEIOLHIWUKV-UHFFFAOYSA-N 0.000 description 1
- CIQOKNCZASDWPT-UHFFFAOYSA-N 7-chloro-5-(2-methylphenyl)-1-(methylsulfonylmethyl)-3h-1,4-benzodiazepin-2-one Chemical compound CC1=CC=CC=C1C1=NCC(=O)N(CS(C)(=O)=O)C2=CC=C(Cl)C=C12 CIQOKNCZASDWPT-UHFFFAOYSA-N 0.000 description 1
- WWRGEVQWZDHVRO-UHFFFAOYSA-N 7-chloro-5-(2-methylphenyl)-1-(propylsulfinylmethyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)CCC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1C WWRGEVQWZDHVRO-UHFFFAOYSA-N 0.000 description 1
- SYPQIUYRBDCSOF-UHFFFAOYSA-N 7-chloro-5-(2-methylphenyl)-1-(propylsulfonylmethyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)(=O)CCC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1C SYPQIUYRBDCSOF-UHFFFAOYSA-N 0.000 description 1
- GLTKQZURWSZESR-UHFFFAOYSA-N 7-chloro-5-(4-chloro-2-fluorophenyl)-1-(ethylsulfonylmethyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)(=O)CC)C2=CC=C(Cl)C=C2C=1C1=CC=C(Cl)C=C1F GLTKQZURWSZESR-UHFFFAOYSA-N 0.000 description 1
- YFXGHDPLRNDUKC-UHFFFAOYSA-N 7-chloro-5-(4-chloro-2-methylphenyl)-1-(methylsulfinylmethyl)-3h-1,4-benzodiazepin-2-one Chemical compound CC1=CC(Cl)=CC=C1C1=NCC(=O)N(CS(C)=O)C2=CC=C(Cl)C=C12 YFXGHDPLRNDUKC-UHFFFAOYSA-N 0.000 description 1
- JZGQHIRZWIZFJZ-UHFFFAOYSA-N 7-chloro-5-phenyl-1-(propan-2-ylsulfinylmethyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)C(C)C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 JZGQHIRZWIZFJZ-UHFFFAOYSA-N 0.000 description 1
- NCWFJPFNSGVLFC-UHFFFAOYSA-N 7-chloro-5-phenyl-1-(propylsulfinylmethyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)CCC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 NCWFJPFNSGVLFC-UHFFFAOYSA-N 0.000 description 1
- XLWBJBOAIOXJFE-UHFFFAOYSA-N 7-chloro-5-phenyl-1-(propylsulfonylmethyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)(=O)CCC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 XLWBJBOAIOXJFE-UHFFFAOYSA-N 0.000 description 1
- UHFUEVXPMIADLP-UHFFFAOYSA-N 7-methoxy-1-(methylsulfinylmethyl)-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound C12=CC(OC)=CC=C2N(CS(C)=O)C(=O)CN=C1C1=CC=CC=C1 UHFUEVXPMIADLP-UHFFFAOYSA-N 0.000 description 1
- DRLUVBGGFWKCIC-UHFFFAOYSA-N 7-methoxy-1-(methylsulfonylmethyl)-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound C12=CC(OC)=CC=C2N(CS(C)(=O)=O)C(=O)CN=C1C1=CC=CC=C1 DRLUVBGGFWKCIC-UHFFFAOYSA-N 0.000 description 1
- CASWPYNIADWSGD-UHFFFAOYSA-N 7-nitro-5-phenyl-1-(propylsulfinylmethyl)-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(CS(=O)CCC)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 CASWPYNIADWSGD-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000001118 alkylidene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- 229940124575 antispasmodic agent Drugs 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- GSEZYWGNEACOIW-UHFFFAOYSA-N bis(2-aminophenyl)methanone Chemical compound NC1=CC=CC=C1C(=O)C1=CC=CC=C1N GSEZYWGNEACOIW-UHFFFAOYSA-N 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229960004782 chlordiazepoxide Drugs 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229940093915 gynecological organic acid Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
- 229960002456 hexobarbital Drugs 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 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
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000004967 organic peroxy acids Chemical class 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VYGSFTVYZHNGBU-UHFFFAOYSA-N trichloromethanesulfonic acid Chemical compound OS(=O)(=O)C(Cl)(Cl)Cl VYGSFTVYZHNGBU-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- 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
-
- 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
- C07D243/28—Preparation including building-up the benzodiazepine skeleton from compounds containing no hetero rings
-
- 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
- C07D243/30—Preparation including building-up the benzodiazepine skeleton from compounds already containing hetero rings
-
- 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
- C07D243/30—Preparation including building-up the benzodiazepine skeleton from compounds already containing hetero rings
- C07D243/36—Preparation including building-up the benzodiazepine skeleton from compounds already containing hetero rings containing an indole or hydrogenated indole ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP5552970A JPS4831118B1 (enrdf_load_stackoverflow) | 1970-06-24 | 1970-06-24 |
Publications (1)
Publication Number | Publication Date |
---|---|
CH578545A5 true CH578545A5 (en) | 1976-08-13 |
Family
ID=13001241
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH104576A CH578545A5 (en) | 1970-06-24 | 1976-01-28 | Cns-active 1-subst 1,4-benzodiazepin-2-ones |
Country Status (6)
Country | Link |
---|---|
JP (1) | JPS4831118B1 (enrdf_load_stackoverflow) |
AT (1) | AT306733B (enrdf_load_stackoverflow) |
CH (1) | CH578545A5 (enrdf_load_stackoverflow) |
CS (1) | CS179398B2 (enrdf_load_stackoverflow) |
HU (1) | HU163792B (enrdf_load_stackoverflow) |
PL (1) | PL92569B1 (enrdf_load_stackoverflow) |
-
1970
- 1970-06-24 JP JP5552970A patent/JPS4831118B1/ja active Pending
-
1971
- 1971-01-27 HU HUSU000745 patent/HU163792B/hu unknown
- 1971-01-28 AT AT352672A patent/AT306733B/de not_active IP Right Cessation
- 1971-02-01 CS CS426571A patent/CS179398B2/cs unknown
- 1971-02-02 PL PL18373771A patent/PL92569B1/pl unknown
-
1976
- 1976-01-28 CH CH104576A patent/CH578545A5/de not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
JPS4831118B1 (enrdf_load_stackoverflow) | 1973-09-26 |
PL92569B1 (enrdf_load_stackoverflow) | 1977-04-30 |
AT306733B (de) | 1973-04-25 |
HU163792B (enrdf_load_stackoverflow) | 1973-10-27 |
CS179398B2 (en) | 1977-10-31 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE2037693A1 (de) | Chinazolinderivate,verfahren zu ihrer herstellung und ihre verwendung | |
CH632511A5 (de) | Verfahren zur herstellung von diazepinderivaten. | |
CH532065A (de) | Verfahren zur Herstellung von Benzodiazepinderivaten | |
DE1955349C2 (de) | s-Triazolo [4,3-a] [1,4] benzodiazepine | |
DE1920207A1 (de) | Verfahren zur Herstellung von 1,4-Benzodiazepin-2-onverbindungen | |
CH578545A5 (en) | Cns-active 1-subst 1,4-benzodiazepin-2-ones | |
DE2166472A1 (de) | Verfahren zur herstellung von 1,3dihydro-2h-1,4-benzodiazepin-2-onen | |
EP0072029A2 (de) | Triazolobenzazepine, Verfahren und Zwischenprodukte zu deren Herstellung und diese enthaltende Arzneimittel | |
DE1695211A1 (de) | Verfahren zur Herstellung von Benzodiazepin-Derivaten | |
DE2166504C3 (enrdf_load_stackoverflow) | ||
DE2104571C3 (de) | S-Phenyl-1,3-dihydro-2H-1,4benzodiazepin-2-one, ihre Salze und diese Verbindungen enthaltende Arzneipräparate | |
DE2141443C3 (de) | U-Dihydro-S-phenyl^H-M-benzodiazepin-2-one, ihre Salze, Verfahren zu ihrer Herstellung und Arzneimittel | |
CH581633A5 (en) | Cns-active 1-subst 1,4-benzodiazepin-2-ones | |
DE2016385C3 (de) | 1 -Alkoxyalkyl-5-(o-fluorphenyl)-7chlor-13-dihydro-2H-benzodiazepin-2-onderivate | |
DE2017060C3 (de) | Verfahren zur Herstellung von 1,3-Dihydro-2H-1,4-benzodiazepinon-(2)derivaten | |
DE2166866C3 (de) | 1 -Phenylalkoxyäthyl-13-dihydro-5phenyl-2H-1,4-benzodiazepin-2-one | |
DE2119717C3 (de) | 14.05.70 Japan 41499-70 1-Alkoxyalkyl-5-(o-tolyl)-7-chlor-1,3-dihydro-2H-1 ^-benzodiazepin Verbindungen, ihre Salze, Verfahren zu ihrer Herstellung und diese Verbindungen | |
AT395154B (de) | Verfahren zur herstellung von neuen imidazo(1,5-a)(1,4)diazepinverbindungen | |
DE2541464A1 (de) | 1,2,4-triazolderivate, verfahren zur herstellung derselben und diese enthaltende pharmazeutische mittel | |
DE2104571A1 (de) | Benzodiazepine, Verfahren zu ihrer Herstellung und Arzneipraparate | |
DE2204484A1 (de) | Verfahren zur herstellung von 1,4benzodiazepinen | |
AT330787B (de) | Verfahren zur herstellung von neuen diazepinderivaten und deren salzen | |
DE1795372C3 (de) | 10.01.68 Japan 1501-68 Verfahren zur Herstellung von 5-(o-Halogenphenyl)-7-halogen-1,3-dihydro-2H-1,4-benzodiazepin-2-onen und 2-Aminomethylindole und ihre Salze | |
DE2129647C3 (de) | Verfahren zur Herstellung von 1-Hydroxyalkyl-5-(o-halogenphenyl)-1,3dihydro-2 H -1,4-benzodiazepin-2-onderivaten | |
AT276400B (de) | Verfahren zur Herstellung von neuen Benzodiazepin-Derivaten und von deren Säureadditionssalzen und quaternären Salzen |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PL | Patent ceased | ||
PL | Patent ceased |