NO121951B - - Google Patents
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- Publication number
- NO121951B NO121951B NO4919/68A NO491968A NO121951B NO 121951 B NO121951 B NO 121951B NO 4919/68 A NO4919/68 A NO 4919/68A NO 491968 A NO491968 A NO 491968A NO 121951 B NO121951 B NO 121951B
- Authority
- NO
- Norway
- Prior art keywords
- formula
- hydrogen
- reaction
- chloro
- dihydro
- Prior art date
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- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 239000000543 intermediate Substances 0.000 claims description 4
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims description 3
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 claims 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 11
- -1 quinazoline compound Chemical class 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 239000003054 catalyst 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
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 229910000365 copper sulfate Inorganic materials 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003246 quinazolines Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LVHORFVCJPVJTA-UHFFFAOYSA-N ClC=1C=C2C(=[N+](C(NC2=CC1)(CCl)CCl)[O-])C1=CC=CC=C1 Chemical compound ClC=1C=C2C(=[N+](C(NC2=CC1)(CCl)CCl)[O-])C1=CC=CC=C1 LVHORFVCJPVJTA-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 150000001879 copper Chemical class 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 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 2
- SUNMBRGCANLOEG-UHFFFAOYSA-N 1,3-dichloroacetone Chemical compound ClCC(=O)CCl SUNMBRGCANLOEG-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 239000000538 analytical sample Substances 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
- 229960004132 diethyl ether Drugs 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-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
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- SFPLCXSRUNUDRX-UHFFFAOYSA-N ClCC1NC2=CC=C(C=C2C(=[N+]1[O-])C1=CC=CC=C1)Cl Chemical compound ClCC1NC2=CC=C(C=C2C(=[N+]1[O-])C1=CC=CC=C1)Cl SFPLCXSRUNUDRX-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
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 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
- 230000009286 beneficial effect Effects 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 229940049706 benzodiazepine Drugs 0.000 description 1
- 239000012267 brine Substances 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
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 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
- 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
- 239000000155 melt Substances 0.000 description 1
- LGRLWUINFJPLSH-UHFFFAOYSA-N methanide Chemical compound [CH3-] LGRLWUINFJPLSH-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZRLVQFQTCMUIRM-UHFFFAOYSA-N potassium;2-methylbutan-2-olate Chemical compound [K+].CCC(C)(C)[O-] ZRLVQFQTCMUIRM-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- DZHAYSANSDYBFE-UHFFFAOYSA-N sodium;diethylazanide Chemical compound [Na+].CC[N-]CC DZHAYSANSDYBFE-UHFFFAOYSA-N 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 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
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
Landscapes
- 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)
- Glass Compositions (AREA)
- Surface Treatment Of Glass Fibres Or Filaments (AREA)
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
- Moulding By Coating Moulds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO4919/68A NO121951B (da) | 1964-04-10 | 1968-12-09 |
Applications Claiming Priority (10)
| 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 |
| NO160742A NO122653B (da) | 1964-04-10 | 1965-12-02 | |
| US73548468A | 1968-04-09 | 1968-04-09 | |
| US73547868A | 1968-04-09 | 1968-04-09 | |
| US73547668A | 1968-04-09 | 1968-04-09 | |
| US73547968A | 1968-04-09 | 1968-04-09 | |
| US73547568A | 1968-04-09 | 1968-04-09 | |
| NO4919/68A NO121951B (da) | 1964-04-10 | 1968-12-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO121951B true NO121951B (da) | 1971-05-03 |
Family
ID=27575413
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO160742A NO122653B (da) | 1964-04-10 | 1965-12-02 | |
| NO160740A NO121607B (da) | 1964-04-10 | 1965-12-02 | |
| NO160741A NO120476B (da) | 1964-04-10 | 1965-12-02 | |
| NO4919/68A NO121951B (da) | 1964-04-10 | 1968-12-09 |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO160742A NO122653B (da) | 1964-04-10 | 1965-12-02 | |
| NO160740A NO121607B (da) | 1964-04-10 | 1965-12-02 | |
| NO160741A NO120476B (da) | 1964-04-10 | 1965-12-02 |
Country Status (14)
| Country | Link |
|---|---|
| US (5) | US3523972A (da) |
| BE (6) | BE662354A (da) |
| BR (5) | BR6568738D0 (da) |
| CH (10) | CH507259A (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) | NO122653B (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 |
| WO2004035581A1 (ja) * | 2002-10-18 | 2004-04-29 | Ono Pharmaceutical Co., Ltd. | スピロ複素環誘導体化合物およびその化合物を有効成分とする薬剤 |
| 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 | ||
| US3311612A (en) * | 1967-03-28 | Process for preparing | ||
| US3179656A (en) * | 1965-04-20 | Azepine x-oxidss | ||
| 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 CH1663168A patent/CH507259A/de not_active IP Right Cessation
- 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
- 1965-04-06 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 BE BE662354D patent/BE662354A/xx unknown
- 1965-04-09 DK DK182565AA patent/DK121123B/da unknown
- 1965-04-09 SE SE04688/65A patent/SE338779B/xx unknown
- 1965-04-09 FR FR12562A patent/FR4621M/fr not_active Expired
- 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 SE14586/67A patent/SE318282B/xx unknown
- 1965-09-29 SE SE12612/65A patent/SE318281B/xx unknown
- 1965-11-21 IL IL24659A patent/IL24659A/en unknown
- 1965-11-21 IL IL24658A patent/IL24658A/xx 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 CH1632265A patent/CH462177A/de unknown
- 1965-11-26 CH CH1904168A patent/CH469722A/de unknown
- 1965-11-26 CH CH1632365A patent/CH462832A/de unknown
- 1965-11-29 DE DE19651545975 patent/DE1545975A1/de active Pending
- 1965-11-29 DE DE19651545974 patent/DE1545974A1/de active Pending
- 1965-11-29 DE DE19651545972 patent/DE1545972A1/de active Pending
- 1965-11-29 NL NL6515499A patent/NL6515499A/xx unknown
- 1965-11-30 IL IL24703A patent/IL24703A/en unknown
- 1965-11-30 FR FR40199A patent/FR4904M/fr not_active Expired
- 1965-11-30 FR FR40200A patent/FR1482840A/fr not_active Expired
- 1965-12-01 SE SE15558/65A patent/SE320080B/xx unknown
- 1965-12-01 GB GB36217/66A patent/GB1124248A/en not_active Expired
- 1965-12-01 GB GB50942/65A patent/GB1082444A/en not_active Expired
- 1965-12-01 BE BE673108D patent/BE673108A/xx unknown
- 1965-12-01 GB GB50940/65A patent/GB1124244A/en not_active Expired
- 1965-12-01 BE BE673107D patent/BE673107A/xx unknown
- 1965-12-01 FR FR40400A patent/FR1476609A/fr not_active Expired
- 1965-12-01 GB GB36215/66A patent/GB1124246A/en not_active Expired
- 1965-12-01 BE BE673109D patent/BE673109A/xx unknown
- 1965-12-01 GB GB50943/65A patent/GB1124245A/en not_active Expired
- 1965-12-01 SE SE16559/65A patent/SE320081B/xx unknown
- 1965-12-01 BE BE673106D patent/BE673106A/xx unknown
- 1965-12-01 SE SE9993/69A patent/SE345458B/xx unknown
- 1965-12-01 GB GB36216/66A patent/GB1124247A/en not_active Expired
- 1965-12-01 SE SE15556/65A patent/SE317384B/xx unknown
- 1965-12-01 GB GB50941/65A patent/GB1082165A/en not_active Expired
- 1965-12-01 SE SE9994/69A patent/SE345455B/xx unknown
- 1965-12-02 DK DK621565AA patent/DK117229B/da unknown
- 1965-12-02 NO NO160742A patent/NO122653B/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 NO160740A patent/NO121607B/no unknown
- 1965-12-02 FR FR40552A patent/FR1482841A/fr not_active Expired
- 1965-12-02 FR FR40563A patent/FR1476612A/fr not_active Expired
- 1965-12-02 NO NO160741A patent/NO120476B/no unknown
- 1965-12-02 BR BR175398/65A patent/BR6575398D0/pt unknown
- 1965-12-03 NL NL6515758A patent/NL6515758A/xx unknown
- 1965-12-03 DK DK624065AA patent/DK125555B/da unknown
- 1965-12-03 NL NL6515759A patent/NL131734C/xx active
-
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 US735476*A patent/US3523972A/en not_active Expired - Lifetime
- 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 US735484*A patent/US3485823A/en not_active Expired - Lifetime
- 1968-04-09 US US735475*A patent/US3503975A/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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