NO120476B - - Google Patents
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- Publication number
- NO120476B NO120476B NO160741A NO16074165A NO120476B NO 120476 B NO120476 B NO 120476B NO 160741 A NO160741 A NO 160741A NO 16074165 A NO16074165 A NO 16074165A NO 120476 B NO120476 B NO 120476B
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- benzodiazepine
- dihydro
- oxide
- phenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims description 3
- 150000007529 inorganic bases Chemical class 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- QNFIMGMERSKNTL-UHFFFAOYSA-N ClC=1C=C2C(=[N+](C(NC2=CC1)(C)CCl)[O-])C1=CC=CC=C1 Chemical compound ClC=1C=C2C(=[N+](C(NC2=CC1)(C)CCl)[O-])C1=CC=CC=C1 QNFIMGMERSKNTL-UHFFFAOYSA-N 0.000 claims 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 238000000354 decomposition reaction Methods 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000007868 Raney catalyst Substances 0.000 description 5
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 5
- 229910000564 Raney nickel Inorganic materials 0.000 description 5
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000000538 analytical sample Substances 0.000 description 5
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 5
- -1 lithium aluminum hydride Chemical compound 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- CNBQOYSHHJFXGJ-UHFFFAOYSA-N 7-chloro-2-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine Chemical compound ClC=1C=CC2=C(C(=NCC(N2)C)C2=CC=CC=C2)C1 CNBQOYSHHJFXGJ-UHFFFAOYSA-N 0.000 description 4
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZWWWYOKRVNYQHF-UHFFFAOYSA-N 2,3-dihydro-1h-1,2-benzodiazepine Chemical class C1=CCNNC2=CC=CC=C21 ZWWWYOKRVNYQHF-UHFFFAOYSA-N 0.000 description 3
- MBGNATWIIKSNNI-UHFFFAOYSA-N 2-methyl-4-oxido-5-phenyl-3H-1,4-benzodiazepin-4-ium Chemical compound CC1=NC2=C(C(=[N+](C1)[O-])C1=CC=CC=C1)C=CC=C2 MBGNATWIIKSNNI-UHFFFAOYSA-N 0.000 description 3
- UNGOBIYYVFAYDT-UHFFFAOYSA-N 2-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine Chemical compound CC1NC2=C(C(=NC1)C1=CC=CC=C1)C=CC=C2 UNGOBIYYVFAYDT-UHFFFAOYSA-N 0.000 description 3
- GKLUBGAXMUNLPW-UHFFFAOYSA-N 7-chloro-2-methyl-4-oxido-5-phenyl-3H-1,4-benzodiazepin-4-ium Chemical compound ClC=1C=CC2=C(C(=[N+](CC(=N2)C)[O-])C2=CC=CC=C2)C1 GKLUBGAXMUNLPW-UHFFFAOYSA-N 0.000 description 3
- ZWQMJAXXCHJSMR-UHFFFAOYSA-N ClC=1C=CC2=C(C(=[N+](CC(N2)C)[O-])C2=CC=CC=C2)C1 Chemical compound ClC=1C=CC2=C(C(=[N+](CC(N2)C)[O-])C2=CC=CC=C2)C1 ZWQMJAXXCHJSMR-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001557 benzodiazepines Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 150000003246 quinazolines Chemical class 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- NUTBMPXAQFUZNM-UHFFFAOYSA-N 2-methyl-5-phenyl-3H-1,4-benzodiazepine Chemical compound CC1=NC2=C(C(=NC1)C1=CC=CC=C1)C=CC=C2 NUTBMPXAQFUZNM-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- LKUYDJYQYPWZDG-UHFFFAOYSA-N 7-chloro-2-methyl-5-phenyl-3H-1,4-benzodiazepine Chemical compound ClC=1C=CC2=C(C(=NCC(=N2)C)C2=CC=CC=C2)C1 LKUYDJYQYPWZDG-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- DTOGVDLJHZCPHB-UHFFFAOYSA-N CC1(NC2=CC=CC=C2C(=[N+]1[O-])C1=CC=CC=C1)C Chemical compound CC1(NC2=CC=CC=C2C(=[N+]1[O-])C1=CC=CC=C1)C DTOGVDLJHZCPHB-UHFFFAOYSA-N 0.000 description 2
- XQQWPHGNYONDKJ-UHFFFAOYSA-N CC1NC2=C(C(=[N+](C1)[O-])C1=CC=CC=C1)C=CC=C2 Chemical compound CC1NC2=C(C(=[N+](C1)[O-])C1=CC=CC=C1)C=CC=C2 XQQWPHGNYONDKJ-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- ANDFAZOPEFWGGL-UHFFFAOYSA-N ClC=1C=C2C(=[N+](C(NC2=CC1)(C)C)[O-])C1=CC=CC=C1 Chemical compound ClC=1C=C2C(=[N+](C(NC2=CC1)(C)C)[O-])C1=CC=CC=C1 ANDFAZOPEFWGGL-UHFFFAOYSA-N 0.000 description 2
- PFRMBGWPEZSQEL-UHFFFAOYSA-N ClC=1C=C2C(=[N+](C(NC2=CC1)(C)Cl)[O-])C1=C(C=CC=C1)C Chemical compound ClC=1C=C2C(=[N+](C(NC2=CC1)(C)Cl)[O-])C1=C(C=CC=C1)C PFRMBGWPEZSQEL-UHFFFAOYSA-N 0.000 description 2
- CSOVSTDKURWFIR-UHFFFAOYSA-N ClCC1(NC2=CC=CC=C2C(=[N+]1[O-])C1=CC=CC=C1)C Chemical compound ClCC1(NC2=CC=CC=C2C(=[N+]1[O-])C1=CC=CC=C1)C CSOVSTDKURWFIR-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-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
- STLNPQQBAZTBIO-FYWRMAATSA-N (ne)-n-[(2-aminophenyl)-phenylmethylidene]hydroxylamine Chemical compound NC1=CC=CC=C1\C(=N\O)C1=CC=CC=C1 STLNPQQBAZTBIO-FYWRMAATSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- GWVZPZZPRYMVHC-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1H-1,2-benzodiazepin-4-ol Chemical class N1NCC(CC2=C1C=CC=C2)O GWVZPZZPRYMVHC-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-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
- 150000007513 acids Chemical class 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229940049706 benzodiazepine Drugs 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 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
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000006049 ring expansion reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005406 washing Methods 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
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/34—Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions
- C03C17/36—Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions at least one coating being a metal
- C03C17/3602—Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions at least one coating being a metal the metal being present as a layer
- C03C17/3668—Surface treatment of glass, not in the form of fibres or filaments, by coating with at least two coatings having different compositions at least one coating being a metal the metal being present as a layer the multilayer coating having electrical properties
-
- 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
-
- 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/10—Spiro-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
- C09K5/08—Materials not undergoing a change of physical state when used
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Combustion & Propulsion (AREA)
- Thermal Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
- Moulding By Coating Moulds (AREA)
- Glass Compositions (AREA)
- Surface Treatment Of Glass Fibres Or Filaments (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35891964A | 1964-04-10 | 1964-04-10 | |
| US40019364A | 1964-09-29 | 1964-09-29 | |
| US415793A US3398139A (en) | 1964-04-10 | 1964-12-03 | Process for preparing 2-amino-benzodiazepines |
| US73547568A | 1968-04-09 | 1968-04-09 | |
| US73547668A | 1968-04-09 | 1968-04-09 | |
| US73547968A | 1968-04-09 | 1968-04-09 | |
| US73547868A | 1968-04-09 | 1968-04-09 | |
| US73548468A | 1968-04-09 | 1968-04-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO120476B true NO120476B (da) | 1970-10-26 |
Family
ID=27575413
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO160740A NO121607B (da) | 1964-04-10 | 1965-12-02 | |
| NO160741A NO120476B (da) | 1964-04-10 | 1965-12-02 | |
| NO160742A NO122653B (da) | 1964-04-10 | 1965-12-02 | |
| NO4919/68A NO121951B (da) | 1964-04-10 | 1968-12-09 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO160740A NO121607B (da) | 1964-04-10 | 1965-12-02 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO160742A NO122653B (da) | 1964-04-10 | 1965-12-02 | |
| NO4919/68A NO121951B (da) | 1964-04-10 | 1968-12-09 |
Country Status (14)
| Country | Link |
|---|---|
| US (5) | US3485841A (da) |
| BE (6) | BE662354A (da) |
| BR (5) | BR6568738D0 (da) |
| CH (10) | CH507215A (da) |
| DE (8) | DE1618518A1 (da) |
| DK (7) | DK121123B (da) |
| FI (1) | FI46965C (da) |
| FR (8) | FR1459759A (da) |
| GB (10) | GB1082163A (da) |
| IL (5) | IL23270A (da) |
| MY (2) | MY6800112A (da) |
| NL (8) | NL6504628A (da) |
| NO (4) | NO121607B (da) |
| SE (9) | SE338779B (da) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4238610A (en) * | 1979-12-20 | 1980-12-09 | Hoffmann-La Roche Inc. | Intermediates for the production of imidazobenzodiazepines |
| CA1157855A (en) * | 1980-07-31 | 1983-11-29 | Albert E. Fischli | Benzodiazepine derivatives |
| US4472435A (en) * | 1980-07-31 | 1984-09-18 | Hoffman-La Roche Inc. | Benzophenone derivatives useful in treating heart failure |
| US5326765A (en) * | 1990-02-14 | 1994-07-05 | Ortho Pharmaceutical Corporation | 2,2,4-trialkyl-1,2-dihydroquinazoline-3-oxides |
| US20060019977A1 (en) * | 2002-10-18 | 2006-01-26 | Ono Pharmaceutical Co., Ltd. | Spiroheterocyclic derivative compounds and drugs comprising the compound as the active ingredient |
| US7086167B2 (en) * | 2004-04-16 | 2006-08-08 | Empire Level Mfg. Corp. | Overmolded vial for use with a level |
| CN115108968A (zh) * | 2021-03-23 | 2022-09-27 | 上药康丽（常州）药业有限公司 | 一种3-(4-溴苯基)-哌啶的生产方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3138586A (en) * | 1964-06-23 | Z-cycloalkylamino derivatives of | ||
| US3179656A (en) * | 1965-04-20 | Azepine x-oxidss | ||
| US3311612A (en) * | 1967-03-28 | Process for preparing | ||
| US3267110A (en) * | 1960-06-03 | 1966-08-16 | Smith Kline French Lab | Trifluoromethyl substituted o-aminophenyl ketones |
| US3389176A (en) * | 1961-09-11 | 1968-06-18 | Hoffmann La Roche | 2-aminophenyl-cycloalkyl-ketoximes |
| US3321467A (en) * | 1963-11-27 | 1967-05-23 | Hoffmann La Roche | 3-halo-1, 4-benzodiazepin-2-ones |
| US3398139A (en) * | 1964-04-10 | 1968-08-20 | Hoffmann La Roche | Process for preparing 2-amino-benzodiazepines |
-
1965
- 1965-03-31 IL IL23270A patent/IL23270A/xx unknown
- 1965-04-02 CH CH1663268A patent/CH507215A/de not_active IP Right Cessation
- 1965-04-02 CH CH461365A patent/CH498844A/de not_active IP Right Cessation
- 1965-04-02 CH CH1663168A patent/CH507259A/de not_active IP Right Cessation
- 1965-04-06 DE DE19651618518 patent/DE1618518A1/de active Pending
- 1965-04-06 DE DE19651695193 patent/DE1695193A1/de active Pending
- 1965-04-06 DE DE19651545942 patent/DE1545942A1/de active Pending
- 1965-04-07 BR BR168738/65A patent/BR6568738D0/pt unknown
- 1965-04-08 GB GB14884/65A patent/GB1082163A/en not_active Expired
- 1965-04-08 FR FR12379A patent/FR1459759A/fr not_active Expired
- 1965-04-09 SE SE04688/65A patent/SE338779B/xx unknown
- 1965-04-09 BE BE662354D patent/BE662354A/xx unknown
- 1965-04-09 FR FR12562A patent/FR4621M/fr not_active Expired
- 1965-04-09 DK DK182565AA patent/DK121123B/da unknown
- 1965-04-12 NL NL6504628A patent/NL6504628A/xx unknown
- 1965-09-01 IL IL24258A patent/IL24258A/en unknown
- 1965-09-10 CH CH1530468A patent/CH470401A/de not_active IP Right Cessation
- 1965-09-10 CH CH1264065A patent/CH470399A/de not_active IP Right Cessation
- 1965-09-14 DE DE19651795500 patent/DE1795500A1/de active Pending
- 1965-09-14 DE DE19651545964 patent/DE1545964A1/de active Pending
- 1965-09-17 GB GB39728/65A patent/GB1082164A/en not_active Expired
- 1965-09-17 GB GB7046/66A patent/GB1124829A/en not_active Expired
- 1965-09-24 DK DK492765AA patent/DK120752B/da unknown
- 1965-09-24 FI FI652286A patent/FI46965C/fi active
- 1965-09-27 FR FR32729A patent/FR1447832A/fr not_active Expired
- 1965-09-27 BE BE670133D patent/BE670133A/xx unknown
- 1965-09-28 BR BR173523/65A patent/BR6573523D0/pt unknown
- 1965-09-29 NL NL6512614A patent/NL6512614A/xx unknown
- 1965-09-29 SE SE12612/65A patent/SE318281B/xx unknown
- 1965-09-29 SE SE14586/67A patent/SE318282B/xx unknown
- 1965-11-21 IL IL24659A patent/IL24659A/en unknown
- 1965-11-21 IL IL24658A patent/IL24658A/xx unknown
- 1965-11-26 CH CH1632365A patent/CH462832A/de unknown
- 1965-11-26 CH CH1632265A patent/CH462177A/de unknown
- 1965-11-26 CH CH1904268A patent/CH487908A/de not_active IP Right Cessation
- 1965-11-26 CH CH1632465A patent/CH469008A/de unknown
- 1965-11-26 CH CH1904168A patent/CH469722A/de unknown
- 1965-11-29 DE DE19651545972 patent/DE1545972A1/de active Pending
- 1965-11-29 DE DE19651545974 patent/DE1545974A1/de active Pending
- 1965-11-29 DE DE19651545975 patent/DE1545975A1/de active Pending
- 1965-11-29 NL NL6515499A patent/NL6515499A/xx unknown
- 1965-11-30 FR FR40199A patent/FR4904M/fr not_active Expired
- 1965-11-30 IL IL24703A patent/IL24703A/en unknown
- 1965-11-30 FR FR40200A patent/FR1482840A/fr not_active Expired
- 1965-12-01 SE SE15556/65A patent/SE317384B/xx unknown
- 1965-12-01 GB GB50943/65A patent/GB1124245A/en not_active Expired
- 1965-12-01 SE SE9994/69A patent/SE345455B/xx unknown
- 1965-12-01 BE BE673106D patent/BE673106A/xx unknown
- 1965-12-01 BE BE673109D patent/BE673109A/xx unknown
- 1965-12-01 FR FR40400A patent/FR1476609A/fr not_active Expired
- 1965-12-01 SE SE16559/65A patent/SE320081B/xx unknown
- 1965-12-01 GB GB36216/66A patent/GB1124247A/en not_active Expired
- 1965-12-01 GB GB36215/66A patent/GB1124246A/en not_active Expired
- 1965-12-01 GB GB50941/65A patent/GB1082165A/en not_active Expired
- 1965-12-01 BE BE673108D patent/BE673108A/xx unknown
- 1965-12-01 BE BE673107D patent/BE673107A/xx unknown
- 1965-12-01 SE SE15558/65A patent/SE320080B/xx unknown
- 1965-12-01 GB GB50942/65A patent/GB1082444A/en not_active Expired
- 1965-12-01 GB GB36217/66A patent/GB1124248A/en not_active Expired
- 1965-12-01 SE SE9993/69A patent/SE345458B/xx unknown
- 1965-12-01 GB GB50940/65A patent/GB1124244A/en not_active Expired
- 1965-12-02 NO NO160740A patent/NO121607B/no unknown
- 1965-12-02 NO NO160741A patent/NO120476B/no unknown
- 1965-12-02 BR BR175394/65A patent/BR6575394D0/pt unknown
- 1965-12-02 BR BR175397/65A patent/BR6575397D0/pt unknown
- 1965-12-02 NO NO160742A patent/NO122653B/no unknown
- 1965-12-02 FR FR40552A patent/FR1482841A/fr not_active Expired
- 1965-12-02 BR BR175398/65A patent/BR6575398D0/pt unknown
- 1965-12-02 DK DK621565AA patent/DK117229B/da unknown
- 1965-12-02 FR FR40563A patent/FR1476612A/fr not_active Expired
- 1965-12-03 NL NL6515759A patent/NL131734C/xx active
- 1965-12-03 DK DK624065AA patent/DK125555B/da unknown
- 1965-12-03 NL NL6515758A patent/NL6515758A/xx unknown
-
1966
- 1966-03-29 DK DK163566AA patent/DK115108B/da unknown
- 1966-03-29 DK DK163466AA patent/DK115851B/da unknown
-
1968
- 1968-02-19 NL NL6802319A patent/NL6802319A/xx unknown
- 1968-04-09 US US735478*A patent/US3485841A/en not_active Expired - Lifetime
- 1968-04-09 US US735479*A patent/US3594364A/en not_active Expired - Lifetime
- 1968-04-09 US US735475*A patent/US3503975A/en not_active Expired - Lifetime
- 1968-04-09 US US735484*A patent/US3485823A/en not_active Expired - Lifetime
- 1968-04-09 US US735476*A patent/US3523972A/en not_active Expired - Lifetime
- 1968-12-09 NO NO4919/68A patent/NO121951B/no unknown
- 1968-12-30 MY MY112/68A patent/MY6800112A/xx unknown
-
1969
- 1969-09-18 SE SE12886/69A patent/SE350756B/xx unknown
- 1969-12-31 MY MY1969183A patent/MY6900183A/xx unknown
-
1970
- 1970-05-14 NL NL7006995A patent/NL7006995A/xx unknown
- 1970-05-14 NL NL7006996A patent/NL7006996A/xx unknown
- 1970-06-10 DK DK301070A patent/DK133155C/da active
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