NO750649L - - Google Patents
Info
- Publication number
- NO750649L NO750649L NO750649A NO750649A NO750649L NO 750649 L NO750649 L NO 750649L NO 750649 A NO750649 A NO 750649A NO 750649 A NO750649 A NO 750649A NO 750649 L NO750649 L NO 750649L
- Authority
- NO
- Norway
- Prior art keywords
- formula
- derivative
- benzodiazepine
- reaction
- dihydro
- Prior art date
Links
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- FQHPKOVQMIHQBR-UHFFFAOYSA-N 2-isocyanatoacetyl chloride Chemical class ClC(=O)CN=C=O FQHPKOVQMIHQBR-UHFFFAOYSA-N 0.000 claims description 13
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 10
- -1 alkoxyalkyloxyalkyl Chemical group 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 8
- 150000008366 benzophenones Chemical class 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 3
- 125000005452 alkenyloxyalkyl group Chemical group 0.000 claims description 3
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical class OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000004385 trihaloalkyl group Chemical group 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000013067 intermediate product Substances 0.000 claims 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001557 benzodiazepines Chemical class 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000007858 starting material Substances 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
- CPEZVJLUFDDWPH-UHFFFAOYSA-N 1,3-dimethyl-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound C12=CC=CC=C2N(C)C(=O)C(C)N=C1C1=CC=CC=C1 CPEZVJLUFDDWPH-UHFFFAOYSA-N 0.000 description 1
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- YVTVBCWQHDDTGB-UHFFFAOYSA-N 5-(2-fluorophenyl)-1-methyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(C)C2=CC=CC=C2C=1C1=CC=CC=C1F YVTVBCWQHDDTGB-UHFFFAOYSA-N 0.000 description 1
- CPTNPLVMZBCJNJ-UHFFFAOYSA-N 5-(2-fluorophenyl)-1-methyl-7-nitro-4,5-dihydro-3h-1,4-benzodiazepin-2-one Chemical compound N1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C1C1=CC=CC=C1F CPTNPLVMZBCJNJ-UHFFFAOYSA-N 0.000 description 1
- FLEQTIDRWGGTRR-UHFFFAOYSA-N 7-bromo-1-methyl-5-phenyl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(C)C2=CC=C(Br)C=C2C=1C1=CC=CC=C1 FLEQTIDRWGGTRR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- OFVXPDXXVSGEPX-UHFFFAOYSA-N Flutoprazepam Chemical compound FC1=CC=CC=C1C(C1=CC(Cl)=CC=C11)=NCC(=O)N1CC1CC1 OFVXPDXXVSGEPX-UHFFFAOYSA-N 0.000 description 1
- UBKVMFUMOAWHGB-UHFFFAOYSA-N N1-(2-Hydroxyethyl)flurazepam Chemical compound N=1CC(=O)N(CCOC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1F UBKVMFUMOAWHGB-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-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
- 238000007351 Smiles rearrangement reaction Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- KIWZKBUUWJTGPP-UHFFFAOYSA-N [2-(methylamino)-5-nitrophenyl]-phenylmethanone Chemical compound CNC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 KIWZKBUUWJTGPP-UHFFFAOYSA-N 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
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 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 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000010446 mirabilite Substances 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [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
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C265/00—Derivatives of isocyanic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic 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 |
|---|---|---|---|
| JP49024622A JPS50116485A (fr) | 1974-02-27 | 1974-02-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO750649L true NO750649L (fr) | 1975-08-28 |
Family
ID=12143235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO750649A NO750649L (fr) | 1974-02-27 | 1975-02-26 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3991048A (fr) |
| JP (1) | JPS50116485A (fr) |
| AT (1) | AT341530B (fr) |
| BE (1) | BE825983A (fr) |
| CA (1) | CA1038382A (fr) |
| CH (1) | CH599175A5 (fr) |
| DE (1) | DE2508332A1 (fr) |
| DK (1) | DK138267B (fr) |
| FI (1) | FI750487A (fr) |
| FR (1) | FR2262037B1 (fr) |
| GB (1) | GB1460403A (fr) |
| HU (1) | HU170222B (fr) |
| NL (1) | NL7501958A (fr) |
| NO (1) | NO750649L (fr) |
| SE (1) | SE7501867L (fr) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2450825A1 (fr) * | 1979-03-09 | 1980-10-03 | Synthelabo | Derives de benzodiazepine et leur application en therapeutique |
| JPH0780858B2 (ja) * | 1987-10-19 | 1995-08-30 | 住友化学工業株式会社 | 放射性ベンゾジアゼピン誘導体およびその製造法 |
| US5216147A (en) * | 1987-10-19 | 1993-06-01 | Sumitomo Chemical Company, Limited | Radioactive benzodiazepine derivatives |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3371085A (en) * | 1959-12-10 | 1968-02-27 | Hoffmann La Roche | 5-aryl-3h-1,4-benzodiazepin-2(1h)-ones |
-
1974
- 1974-02-27 JP JP49024622A patent/JPS50116485A/ja active Pending
-
1975
- 1975-02-19 SE SE7501867A patent/SE7501867L/xx unknown
- 1975-02-19 NL NL7501958A patent/NL7501958A/xx not_active Application Discontinuation
- 1975-02-21 FI FI750487A patent/FI750487A/fi not_active Application Discontinuation
- 1975-02-24 AT AT137375A patent/AT341530B/de not_active IP Right Cessation
- 1975-02-25 US US05/552,888 patent/US3991048A/en not_active Expired - Lifetime
- 1975-02-25 GB GB787075A patent/GB1460403A/en not_active Expired
- 1975-02-26 CH CH240575A patent/CH599175A5/xx not_active IP Right Cessation
- 1975-02-26 NO NO750649A patent/NO750649L/no unknown
- 1975-02-26 DE DE19752508332 patent/DE2508332A1/de active Pending
- 1975-02-26 FR FR7505959A patent/FR2262037B1/fr not_active Expired
- 1975-02-26 CA CA220,821A patent/CA1038382A/fr not_active Expired
- 1975-02-26 DK DK76375AA patent/DK138267B/da unknown
- 1975-02-26 BE BE153740A patent/BE825983A/fr unknown
- 1975-02-27 HU HUSU891A patent/HU170222B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1038382A (fr) | 1978-09-12 |
| DE2508332A1 (de) | 1975-09-04 |
| JPS50116485A (fr) | 1975-09-11 |
| BE825983A (fr) | 1975-06-16 |
| NL7501958A (nl) | 1975-08-29 |
| FR2262037A1 (fr) | 1975-09-19 |
| AU7856075A (en) | 1976-08-26 |
| DK76375A (fr) | 1975-10-20 |
| FR2262037B1 (fr) | 1977-11-18 |
| HU170222B (fr) | 1977-04-28 |
| DK138267C (fr) | 1979-03-05 |
| CH599175A5 (fr) | 1978-05-12 |
| DK138267B (da) | 1978-08-07 |
| US3991048A (en) | 1976-11-09 |
| FI750487A (fr) | 1975-08-28 |
| ATA137375A (de) | 1977-06-15 |
| GB1460403A (en) | 1977-01-06 |
| AT341530B (de) | 1978-02-10 |
| SE7501867L (fr) | 1975-08-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1090333A (fr) | Procede de production de derives de la diazepine | |
| SE449098B (sv) | Fenyl-/2-(5-hydroxi-1-imidazolyl)fenyl/-metanonderivat till anvendning som mellanprodukter for framstellning av imidazo/1,5-a//1,4/bensodiazepinderivat | |
| CH630381A5 (de) | Verfahren zur herstellung von diazepinderivaten. | |
| NO118914B (fr) | ||
| DE2323149A1 (de) | Thienopyrimidine, verfahren zu deren herstellung und diese verbindungen enthaltende arzneipraeparate | |
| US3573308A (en) | 3-lower alkoxy methyl-3,4-dihydro-4-hydroxy-4-aryl quinazolin-2(1h) ones and related compounds | |
| CA1049009A (fr) | 6h-thieno (3,2-f)-s-triazolo (4,3-a) (1,4) diazepines | |
| NO750649L (fr) | ||
| NO117366B (fr) | ||
| US3784542A (en) | Benzodiazepin-2-ones | |
| NO126799B (fr) | ||
| US4116956A (en) | Benzodiazepine derivatives | |
| US3513158A (en) | Process for preparing 5-aryl benzodiazepines and intermediates | |
| US4579685A (en) | Process for preparing 1-substituted-1,4-benzodiazepine derivatives | |
| NO132800B (fr) | ||
| DK156391B (da) | Analogifremgangsmaade til fremstilling af 3-aminopyrrolderivater | |
| US3849434A (en) | Process for preparing triazolobenzodiazepines | |
| CA1055491A (fr) | Procede pour la fabrication de derives de la benzodiazepine | |
| CA1049514A (fr) | Benzodiazepines-1,4 | |
| US3503966A (en) | 4-aryl-3,1-benzothiazin-2-one and 4-aryl-3,1-benzothiazine-2-thione | |
| US3991070A (en) | Process for preparing halo triazolo benzodiazepine | |
| US3746701A (en) | Method for the production of benzodiazepine derivatives | |
| US3524848A (en) | Process for producing benzodiazepine derivatives | |
| US3446800A (en) | Process for the preparation of 1,3-dihydro-2h-1,4-benzodiazepin-2-ones | |
| KR800001087B1 (ko) | 디아제핀 유도체의 제조방법 |