NO124645B - - Google Patents
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- NO124645B NO124645B NO2421/69A NO242169A NO124645B NO 124645 B NO124645 B NO 124645B NO 2421/69 A NO2421/69 A NO 2421/69A NO 242169 A NO242169 A NO 242169A NO 124645 B NO124645 B NO 124645B
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- Norway
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- 150000001875 compounds Chemical class 0.000 claims abstract 21
- 150000003839 salts Chemical class 0.000 claims abstract 14
- 239000002253 acid Substances 0.000 claims abstract 12
- 239000001257 hydrogen Substances 0.000 claims abstract 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 12
- -1 benzodiazepine ester Chemical class 0.000 claims abstract 10
- 238000000034 method Methods 0.000 claims abstract 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 8
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims abstract 7
- 238000004519 manufacturing process Methods 0.000 claims abstract 7
- 229910052707 ruthenium Inorganic materials 0.000 claims abstract 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract 6
- 150000002367 halogens Chemical class 0.000 claims abstract 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract 4
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims abstract 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract 4
- 239000000460 chlorine Substances 0.000 claims abstract 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 4
- 150000002431 hydrogen Chemical class 0.000 claims abstract 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 3
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims abstract 2
- 239000012458 free base Substances 0.000 claims abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- 241000112708 Vates Species 0.000 claims 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 21
- 239000000463 material Substances 0.000 abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 21
- 239000000243 solution Substances 0.000 abstract 21
- 238000012360 testing method Methods 0.000 abstract 18
- 241001465754 Metazoa Species 0.000 abstract 17
- 239000000203 mixture Substances 0.000 abstract 17
- 238000002844 melting Methods 0.000 abstract 16
- 230000008018 melting Effects 0.000 abstract 16
- 241000699670 Mus sp. Species 0.000 abstract 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 12
- 239000000047 product Substances 0.000 abstract 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 10
- 238000006243 chemical reaction Methods 0.000 abstract 10
- 238000003756 stirring Methods 0.000 abstract 10
- 206010010904 Convulsion Diseases 0.000 abstract 9
- 230000000694 effects Effects 0.000 abstract 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 8
- 238000001816 cooling Methods 0.000 abstract 8
- 239000000126 substance Substances 0.000 abstract 8
- 238000002425 crystallisation Methods 0.000 abstract 7
- 230000008025 crystallization Effects 0.000 abstract 7
- 238000002474 experimental method Methods 0.000 abstract 7
- 238000001914 filtration Methods 0.000 abstract 7
- 230000007935 neutral effect Effects 0.000 abstract 7
- 239000007787 solid Substances 0.000 abstract 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 6
- 239000000706 filtrate Substances 0.000 abstract 6
- 239000000725 suspension Substances 0.000 abstract 6
- MEXNZUOOCNBUJU-UHFFFAOYSA-N (2-chlorophenyl)-pyrimidin-2-ylmethanone Chemical compound ClC1=CC=CC=C1C(=O)C1=NC=CC=N1 MEXNZUOOCNBUJU-UHFFFAOYSA-N 0.000 abstract 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 5
- 241000282326 Felis catus Species 0.000 abstract 5
- 230000036461 convulsion Effects 0.000 abstract 5
- 239000003921 oil Substances 0.000 abstract 5
- 235000019198 oils Nutrition 0.000 abstract 5
- 238000000746 purification Methods 0.000 abstract 5
- 239000002904 solvent Substances 0.000 abstract 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 4
- 230000001773 anti-convulsant effect Effects 0.000 abstract 4
- 239000013078 crystal Substances 0.000 abstract 4
- 238000004821 distillation Methods 0.000 abstract 4
- 238000001704 evaporation Methods 0.000 abstract 4
- 239000011541 reaction mixture Substances 0.000 abstract 4
- WOCIAKWEIIZHES-UHFFFAOYSA-N ruthenium(iv) oxide Chemical compound O=[Ru]=O WOCIAKWEIIZHES-UHFFFAOYSA-N 0.000 abstract 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 abstract 4
- CLUHZXYQKUXOOL-UHFFFAOYSA-N 1-methyl-7-nitro-5-pyrimidin-2-yl-2,3-dihydro-1,4-benzodiazepine Chemical compound C12=CC([N+]([O-])=O)=CC=C2N(C)CCN=C1C1=NC=CC=N1 CLUHZXYQKUXOOL-UHFFFAOYSA-N 0.000 abstract 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 3
- 150000001557 benzodiazepines Chemical class 0.000 abstract 3
- 238000009835 boiling Methods 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 239000012043 crude product Substances 0.000 abstract 3
- 238000000354 decomposition reaction Methods 0.000 abstract 3
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 abstract 3
- 230000008020 evaporation Effects 0.000 abstract 3
- 238000000605 extraction Methods 0.000 abstract 3
- 210000000548 hind-foot Anatomy 0.000 abstract 3
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 abstract 3
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 3
- 238000010992 reflux Methods 0.000 abstract 3
- 230000001624 sedative effect Effects 0.000 abstract 3
- ZAICQJHRVHLVEY-UHFFFAOYSA-N 2-(2-chlorophenyl)-2-pyrimidin-2-ylacetonitrile Chemical compound ClC1=CC=CC=C1C(C#N)C1=NC=CC=N1 ZAICQJHRVHLVEY-UHFFFAOYSA-N 0.000 abstract 2
- BSFOWENCYDHTPW-UHFFFAOYSA-N 7-nitro-5-pyrimidin-2-yl-2,3-dihydro-1h-1,4-benzodiazepine Chemical compound C12=CC([N+](=O)[O-])=CC=C2NCCN=C1C1=NC=CC=N1 BSFOWENCYDHTPW-UHFFFAOYSA-N 0.000 abstract 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 abstract 2
- 241000124008 Mammalia Species 0.000 abstract 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 2
- 208000005392 Spasm Diseases 0.000 abstract 2
- 238000010521 absorption reaction Methods 0.000 abstract 2
- 229960000583 acetic acid Drugs 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- 239000001961 anticonvulsive agent Substances 0.000 abstract 2
- 229960003965 antiepileptics Drugs 0.000 abstract 2
- 239000002585 base Substances 0.000 abstract 2
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 abstract 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 abstract 2
- 239000000284 extract Substances 0.000 abstract 2
- 239000005457 ice water Substances 0.000 abstract 2
- 230000007794 irritation Effects 0.000 abstract 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 abstract 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 abstract 2
- 239000002480 mineral oil Substances 0.000 abstract 2
- 235000010446 mineral oil Nutrition 0.000 abstract 2
- 210000003205 muscle Anatomy 0.000 abstract 2
- 239000003158 myorelaxant agent Substances 0.000 abstract 2
- 229910017604 nitric acid Inorganic materials 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- 239000003208 petroleum Substances 0.000 abstract 2
- 239000012071 phase Substances 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 238000002360 preparation method Methods 0.000 abstract 2
- 230000002040 relaxant effect Effects 0.000 abstract 2
- 230000035939 shock Effects 0.000 abstract 2
- 239000012312 sodium hydride Substances 0.000 abstract 2
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 2
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 abstract 2
- 229910052938 sodium sulfate Inorganic materials 0.000 abstract 2
- 235000011152 sodium sulphate Nutrition 0.000 abstract 2
- 239000007858 starting material Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- GUJAGMICFDYKNR-UHFFFAOYSA-N 1,4-benzodiazepine Chemical class N1C=CN=CC2=CC=CC=C12 GUJAGMICFDYKNR-UHFFFAOYSA-N 0.000 abstract 1
- MRDUURPIPLIGQX-UHFFFAOYSA-N 2-(2-chlorophenyl)acetonitrile Chemical compound ClC1=CC=CC=C1CC#N MRDUURPIPLIGQX-UHFFFAOYSA-N 0.000 abstract 1
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical compound ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 abstract 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 abstract 1
- HSJXGZBLRDYBCN-UHFFFAOYSA-N 5-pyrimidin-2-yl-1H-1,4-benzodiazepine Chemical class N1=C(N=CC=C1)C1=NC=CNC2=C1C=CC=C2 HSJXGZBLRDYBCN-UHFFFAOYSA-N 0.000 abstract 1
- MGPDXXHYUGWQSW-UHFFFAOYSA-N 7-chloro-1-methyl-5-pyrimidin-2-yl-2,3-dihydro-1,4-benzodiazepine Chemical compound C12=CC(Cl)=CC=C2N(C)CCN=C1C1=NC=CC=N1 MGPDXXHYUGWQSW-UHFFFAOYSA-N 0.000 abstract 1
- BQZBKGGPTRPZBA-UHFFFAOYSA-N 7-chloro-1-methyl-5-pyrimidin-2-yl-3h-1,4-benzodiazepin-2-one Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=NC=CC=N1 BQZBKGGPTRPZBA-UHFFFAOYSA-N 0.000 abstract 1
- 206010003591 Ataxia Diseases 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 1
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 108010010803 Gelatin Proteins 0.000 abstract 1
- 229920000084 Gum arabic Polymers 0.000 abstract 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 1
- 206010033799 Paralysis Diseases 0.000 abstract 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 238000000297 Sandmeyer reaction Methods 0.000 abstract 1
- 241000978776 Senegalia senegal Species 0.000 abstract 1
- 229920002472 Starch Polymers 0.000 abstract 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 1
- 239000000205 acacia gum Substances 0.000 abstract 1
- 235000010489 acacia gum Nutrition 0.000 abstract 1
- 230000002378 acidificating effect Effects 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 238000010171 animal model Methods 0.000 abstract 1
- 230000002243 anti-metrazol Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 230000000949 anxiolytic effect Effects 0.000 abstract 1
- 239000008346 aqueous phase Substances 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 229940049706 benzodiazepine Drugs 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 235000011089 carbon dioxide Nutrition 0.000 abstract 1
- 239000012876 carrier material Substances 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 229940117975 chromium trioxide Drugs 0.000 abstract 1
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 abstract 1
- 230000002566 clonic effect Effects 0.000 abstract 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- VNEBWJSWMVTSHK-UHFFFAOYSA-L disodium;3-hydroxynaphthalene-2,7-disulfonate Chemical compound [Na+].[Na+].C1=C(S([O-])(=O)=O)C=C2C=C(S([O-])(=O)=O)C(O)=CC2=C1 VNEBWJSWMVTSHK-UHFFFAOYSA-L 0.000 abstract 1
- 239000008298 dragée Substances 0.000 abstract 1
- 239000011363 dried mixture Substances 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 239000003995 emulsifying agent Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000007717 exclusion Effects 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 239000006260 foam Substances 0.000 abstract 1
- 235000019253 formic acid Nutrition 0.000 abstract 1
- 239000008273 gelatin Substances 0.000 abstract 1
- 229920000159 gelatin Polymers 0.000 abstract 1
- 235000019322 gelatine Nutrition 0.000 abstract 1
- 235000011852 gelatine desserts Nutrition 0.000 abstract 1
- 239000012362 glacial acetic acid Substances 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- 229940093915 gynecological organic acid Drugs 0.000 abstract 1
- 230000036571 hydration Effects 0.000 abstract 1
- 238000006703 hydration reaction Methods 0.000 abstract 1
- 150000002430 hydrocarbons Chemical group 0.000 abstract 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 238000002329 infrared spectrum Methods 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000011835 investigation Methods 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 235000019359 magnesium stearate Nutrition 0.000 abstract 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 abstract 1
- 239000011976 maleic acid Substances 0.000 abstract 1
- 238000013508 migration Methods 0.000 abstract 1
- 230000005012 migration Effects 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 235000005985 organic acids Nutrition 0.000 abstract 1
- 239000012074 organic phase Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000003204 osmotic effect Effects 0.000 abstract 1
- 239000007800 oxidant agent Substances 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 238000007911 parenteral administration Methods 0.000 abstract 1
- 230000000144 pharmacologic effect Effects 0.000 abstract 1
- 239000002504 physiological saline solution Substances 0.000 abstract 1
- 229920001515 polyalkylene glycol Polymers 0.000 abstract 1
- 239000002244 precipitate Substances 0.000 abstract 1
- 239000003755 preservative agent Substances 0.000 abstract 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 229930195734 saturated hydrocarbon Natural products 0.000 abstract 1
- 239000000932 sedative agent Substances 0.000 abstract 1
- 239000002002 slurry Substances 0.000 abstract 1
- 235000010288 sodium nitrite Nutrition 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- 239000008107 starch Substances 0.000 abstract 1
- 235000019698 starch Nutrition 0.000 abstract 1
- 230000001954 sterilising effect Effects 0.000 abstract 1
- 238000004659 sterilization and disinfection Methods 0.000 abstract 1
- 239000012258 stirred mixture Substances 0.000 abstract 1
- 239000000829 suppository Substances 0.000 abstract 1
- 208000024891 symptom Diseases 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 239000000454 talc Substances 0.000 abstract 1
- 229910052623 talc Inorganic materials 0.000 abstract 1
- 235000012222 talc Nutrition 0.000 abstract 1
- 238000004809 thin layer chromatography Methods 0.000 abstract 1
- 230000001256 tonic effect Effects 0.000 abstract 1
- 208000028325 tonic-clonic seizure Diseases 0.000 abstract 1
- 230000001988 toxicity Effects 0.000 abstract 1
- 231100000419 toxicity Toxicity 0.000 abstract 1
- 239000003204 tranquilizing agent Substances 0.000 abstract 1
- 230000002936 tranquilizing effect Effects 0.000 abstract 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 abstract 1
- 229940099259 vaseline Drugs 0.000 abstract 1
- 235000015112 vegetable and seed oil Nutrition 0.000 abstract 1
- 239000008158 vegetable oil Substances 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
- 239000000080 wetting agent Substances 0.000 abstract 1
- 239000008096 xylene Substances 0.000 abstract 1
- 230000008439 repair process Effects 0.000 description 3
- 229910001369 Brass Inorganic materials 0.000 description 2
- 239000010951 brass Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 238000012856 packing Methods 0.000 description 2
- 230000002950 deficient Effects 0.000 description 1
- 239000002657 fibrous material Substances 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000004806 packaging method and process 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Manufacture And Refinement Of Metals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US73625068A | 1968-06-12 | 1968-06-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO124645B true NO124645B (xx) | 1972-05-15 |
Family
ID=24959135
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2421/69A NO124645B (xx) | 1968-06-12 | 1969-06-11 | |
| NO2420/69A NO123611B (xx) | 1968-06-12 | 1969-06-14 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2420/69A NO123611B (xx) | 1968-06-12 | 1969-06-14 |
Country Status (7)
| Country | Link |
|---|---|
| BR (2) | BR6909649D0 (xx) |
| DK (1) | DK138075B (xx) |
| ES (1) | ES368238A1 (xx) |
| HU (1) | HU162582B (xx) |
| IL (1) | IL32371A (xx) |
| NO (2) | NO124645B (xx) |
| SE (1) | SE346998B (xx) |
-
1969
- 1969-06-05 SE SE07988/69A patent/SE346998B/xx unknown
- 1969-06-06 DK DK306169AA patent/DK138075B/da unknown
- 1969-06-10 IL IL32371A patent/IL32371A/xx unknown
- 1969-06-11 ES ES368238A patent/ES368238A1/es not_active Expired
- 1969-06-11 BR BR209649/69A patent/BR6909649D0/pt unknown
- 1969-06-11 NO NO2421/69A patent/NO124645B/no unknown
- 1969-06-11 BR BR209650/69A patent/BR6909650D0/pt unknown
- 1969-06-12 HU HUHO1183A patent/HU162582B/hu unknown
- 1969-06-14 NO NO2420/69A patent/NO123611B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR6909650D0 (pt) | 1973-02-22 |
| DK138075B (da) | 1978-07-10 |
| BR6909649D0 (pt) | 1973-02-22 |
| HU162582B (xx) | 1973-03-28 |
| DK138075C (xx) | 1978-12-11 |
| IL32371A (en) | 1972-12-29 |
| SE346998B (xx) | 1972-07-24 |
| NO123611B (xx) | 1971-12-20 |
| ES368238A1 (es) | 1971-05-01 |
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