NO120476B - - Google Patents

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Info

Publication number: NO120476B
Authority: NO; Norway
Prior art keywords: methyl; benzodiazepine; dihydro; oxide; phenyl
Prior art date: 1964-04-10

Application number

NO160741A

Other languages

English (en)

Norwegian (no)

Inventor

G Field

L Sternbach

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1964-04-10

Filing date

1965-12-02

Publication date

1970-10-26

1964-12-03 Priority claimed from US415793A external-priority patent/US3398139A/en

1965-12-02 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1970-10-26 Publication of NO120476B publication Critical patent/NO120476B/no

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)
Glass Compositions (AREA)
Surface Treatment Of Glass Fibres Or Filaments (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
Moulding By Coating Moulds (AREA)

NO160741A 1964-04-10 1965-12-02 NO120476B (pt)

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
US73547868A	1968-04-09	1968-04-09
US73547668A	1968-04-09	1968-04-09
US73547568A	1968-04-09	1968-04-09
US73547968A	1968-04-09	1968-04-09
US73548468A	1968-04-09	1968-04-09

Publications (1)

Publication Number	Publication Date
NO120476B true NO120476B (pt)	1970-10-26

Family

ID=27575413

Family Applications (4)

Application Number	Title	Priority Date
NO160740A NO121607B (pt)	1964-04-10	1965-12-02
NO160742A NO122653B (pt)	1964-04-10	1965-12-02
NO160741A NO120476B (pt)	1964-04-10	1965-12-02
NO4919/68A NO121951B (pt)	1964-04-10	1968-12-09

Family Applications Before (2)

Application Number	Title	Priority Date	Filing Date
NO160740A NO121607B (pt)	1964-04-10	1965-12-02
NO160742A NO122653B (pt)	1964-04-10	1965-12-02

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO4919/68A NO121951B (pt)	1964-04-10	1968-12-09

Country Status (14)

Country	Link
US (5)	US3523972A (pt)
BE (6)	BE662354A (pt)
BR (5)	BR6568738D0 (pt)
CH (10)	CH507259A (pt)
DE (8)	DE1695193A1 (pt)
DK (7)	DK121123B (pt)
FI (1)	FI46965C (pt)
FR (8)	FR1459759A (pt)
GB (10)	GB1082163A (pt)
IL (5)	IL23270A (pt)
MY (2)	MY6800112A (pt)
NL (8)	NL6504628A (pt)
NO (4)	NO121607B (pt)
SE (9)	SE338779B (pt)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
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
US4472435A (en) *	1980-07-31	1984-09-18	Hoffman-La Roche Inc.	Benzophenone derivatives useful in treating heart failure
CA1157855A (en) *	1980-07-31	1983-11-29	Albert E. Fischli	Benzodiazepine derivatives
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)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3311612A (en) *		1967-03-28		Process for preparing
US3179656A (en) *		1965-04-20		Azepine x-oxidss
US3138586A (en) *		1964-06-23		Z-cycloalkylamino derivatives of
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 DE19651695193 patent/DE1695193A1/de active Pending
- 1965-04-06 DE DE19651618518 patent/DE1618518A1/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 FR FR12379A patent/FR1459759A/fr not_active Expired
- 1965-04-08 GB GB14884/65A patent/GB1082163A/en not_active Expired
- 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
- 1965-04-09 SE SE04688/65A patent/SE338779B/xx unknown
- 1965-04-12 NL NL6504628A patent/NL6504628A/xx unknown
- 1965-09-01 IL IL24258A patent/IL24258A/en unknown
- 1965-09-10 CH CH1264065A patent/CH470399A/de not_active IP Right Cessation
- 1965-09-10 CH CH1530468A patent/CH470401A/de not_active IP Right Cessation
- 1965-09-14 DE DE19651545964 patent/DE1545964A1/de active Pending
- 1965-09-14 DE DE19651795500 patent/DE1795500A1/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 BE BE670133D patent/BE670133A/xx unknown
- 1965-09-27 FR FR32729A patent/FR1447832A/fr not_active Expired
- 1965-09-28 BR BR173523/65A patent/BR6573523D0/pt unknown
- 1965-09-29 SE SE12612/65A patent/SE318281B/xx unknown
- 1965-09-29 NL NL6512614A patent/NL6512614A/xx unknown
- 1965-09-29 SE SE14586/67A patent/SE318282B/xx unknown
- 1965-11-21 IL IL24658A patent/IL24658A/xx unknown
- 1965-11-21 IL IL24659A patent/IL24659A/en unknown
- 1965-11-26 CH CH1904268A patent/CH487908A/de not_active IP Right Cessation
- 1965-11-26 CH CH1904168A patent/CH469722A/de unknown
- 1965-11-26 CH CH1632465A patent/CH469008A/de unknown
- 1965-11-26 CH CH1632265A patent/CH462177A/de unknown
- 1965-11-26 CH CH1632365A patent/CH462832A/de unknown
- 1965-11-29 NL NL6515499A patent/NL6515499A/xx unknown
- 1965-11-29 DE DE19651545974 patent/DE1545974A1/de active Pending
- 1965-11-29 DE DE19651545972 patent/DE1545972A1/de active Pending
- 1965-11-29 DE DE19651545975 patent/DE1545975A1/de active Pending
- 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 SE9994/69A patent/SE345455B/xx unknown
- 1965-12-01 FR FR40400A patent/FR1476609A/fr not_active Expired
- 1965-12-01 BE BE673106D patent/BE673106A/xx unknown
- 1965-12-01 BE BE673108D patent/BE673108A/xx unknown
- 1965-12-01 GB GB50942/65A patent/GB1082444A/en not_active Expired
- 1965-12-01 GB GB50943/65A patent/GB1124245A/en not_active Expired
- 1965-12-01 SE SE15558/65A patent/SE320080B/xx unknown
- 1965-12-01 BE BE673109D patent/BE673109A/xx unknown
- 1965-12-01 BE BE673107D patent/BE673107A/xx unknown
- 1965-12-01 GB GB36215/66A patent/GB1124246A/en not_active Expired
- 1965-12-01 GB GB50940/65A patent/GB1124244A/en not_active Expired
- 1965-12-01 SE SE15556/65A patent/SE317384B/xx unknown
- 1965-12-01 GB GB36216/66A patent/GB1124247A/en not_active Expired
- 1965-12-01 SE SE9993/69A patent/SE345458B/xx unknown
- 1965-12-01 GB GB36217/66A patent/GB1124248A/en not_active Expired
- 1965-12-01 GB GB50941/65A patent/GB1082165A/en not_active Expired
- 1965-12-01 SE SE16559/65A patent/SE320081B/xx unknown
- 1965-12-02 FR FR40552A patent/FR1482841A/fr not_active Expired
- 1965-12-02 NO NO160740A patent/NO121607B/no unknown
- 1965-12-02 NO NO160742A patent/NO122653B/no unknown
- 1965-12-02 FR FR40563A patent/FR1476612A/fr not_active Expired
- 1965-12-02 DK DK621565AA patent/DK117229B/da unknown
- 1965-12-02 BR BR175397/65A patent/BR6575397D0/pt unknown
- 1965-12-02 NO NO160741A patent/NO120476B/no unknown
- 1965-12-02 BR BR175398/65A patent/BR6575398D0/pt unknown
- 1965-12-02 BR BR175394/65A patent/BR6575394D0/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 US735484*A patent/US3485823A/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
- 1968-12-09 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 NL7006996A patent/NL7006996A/xx unknown
- 1970-05-14 NL NL7006995A patent/NL7006995A/xx unknown
- 1970-06-10 DK DK301070A patent/DK133155C/da active

Also Published As

Publication number	Publication date
GB1124246A (en)	1968-08-21
MY6800112A (en)	1968-12-31
IL24703A (en)	1969-11-12
BE673109A (pt)	1966-06-01
GB1082165A (en)	1967-09-06
DK125555B (da)	1973-03-05
FR1476609A (fr)	1967-04-14
GB1124829A (en)	1968-08-21
DE1545974A1 (de)	1969-12-11
BE673106A (pt)	1966-06-01
BE662354A (pt)	1965-10-11
BR6575397D0 (pt)	1973-09-06
GB1124245A (en)	1968-08-21
IL24658A (en)	1970-01-29
GB1082164A (en)	1967-09-06
FR1482841A (fr)	1967-06-02
DK115851B (da)	1969-11-17
MY6900183A (en)	1969-12-31
NO121607B (pt)	1971-03-22
BE673108A (pt)	1966-06-01
CH487908A (de)	1970-03-31
GB1082163A (en)	1967-09-06
IL24659A (en)	1970-01-29
CH469008A (de)	1969-02-28
BR6575398D0 (pt)	1973-09-06
CH507259A (de)	1971-05-15
SE320080B (pt)	1970-02-02
CH470399A (de)	1969-03-31
NL131734C (pt)	1971-06-15
CH507215A (de)	1971-05-15
DE1545942A1 (de)	1969-12-18
FI46965C (fi)	1973-08-10
NL6515759A (pt)	1966-06-06
BR6575394D0 (pt)	1973-09-06
SE320081B (pt)	1970-02-02
FR1459759A (fr)	1966-06-17
DK115108B (da)	1969-09-08
GB1124244A (en)	1968-08-21
DK133155C (da)	1976-09-06
SE318282B (pt)	1969-12-08
NL6515499A (pt)	1966-06-06
SE338779B (pt)	1971-09-20
NL6504628A (pt)	1965-10-11
SE345458B (pt)	1972-05-29
DE1545972A1 (de)	1970-07-02
DE1795500A1 (de)	1972-02-03
FR4904M (pt)	1967-04-17
GB1124248A (en)	1968-08-21
DK117229B (da)	1970-03-31
DK120752B (da)	1971-07-12
GB1124247A (en)	1968-08-21
BE673107A (pt)	1966-06-01
NO122653B (pt)	1971-07-26
DE1545964A1 (de)	1970-01-22
GB1082444A (en)	1967-09-06
DE1545975A1 (de)	1969-11-20
NL6802319A (pt)	1968-04-25
SE317384B (pt)	1969-11-17
DE1695193A1 (de)	1971-04-08
CH462832A (de)	1968-09-30
DK133155B (da)	1976-03-29
BE670133A (pt)	1966-03-28
FR1447832A (fr)	1966-07-29
US3503975A (en)	1970-03-31
US3485841A (en)	1969-12-23
BR6573523D0 (pt)	1973-09-11
NL7006996A (pt)	1970-09-23
CH498844A (de)	1970-11-15
FR1476612A (fr)	1967-04-14
NL6512614A (pt)	1966-03-30
BR6568738D0 (pt)	1973-08-07
FR4621M (pt)	1967-01-02
CH469722A (de)	1969-03-15
DE1618518A1 (de)	1971-03-04
US3485823A (en)	1969-12-23
NL6515758A (pt)	1966-06-06
SE345455B (pt)	1972-05-29
SE318281B (pt)	1969-12-08
FR1482840A (fr)	1967-06-02
IL24258A (en)	1969-05-28
SE350756B (pt)	1972-11-06
NL7006995A (pt)	1970-09-23
CH470401A (de)	1969-03-31
FI46965B (pt)	1973-05-02
CH462177A (de)	1968-09-15
US3523972A (en)	1970-08-11
NO121951B (pt)	1971-05-03
US3594364A (en)	1971-07-20
IL23270A (en)	1969-02-27
DK121123B (da)	1971-09-13

Publication	Publication Date	Title
Boyer et al.	1953	Pyrido-2, 3-furoxane1
NO129745B (pt)	1974-05-20
NO120476B (pt)	1970-10-26
US3305553A (en)	1967-02-21	2-aminoquinazoline derivatives
Yates et al.	1971	Carbon disulfide. II. Reaction with active methylene compounds. The structures of the desaurins
FREED et al.	1960	Syntheses of 1, 4-Diazabicyclo [4.4. 0] decanes, 1, 4-Diazabicyclo [4.3. 0] nonanes and 1, 8-Diazabicyclo [4.3. 0] nonanes
NO135277B (pt)	1976-12-06
NO152786B (no)	1985-08-12	Fremgangsmaate ved fremstilling av 10,11-dihydro-5h-dibenzo-(a,d)-cyclohepten-5,10-iminer
Yamanaka	1959	Reaction of 4-Alkoxyquinazolines with Organic Peracid.
Wawzonek et al.	1959	Abnormal Beckmann Rearrangement of 9, 10-Dihydro-9, 10-(11-ketoethano) anthracene Oxime1
Jones et al.	1965	The synthesis of 9-azasteroids—II: Synthesis of β-cyano-and β-carbethoxy-3-and 4-oxo-1, 2, 3, 4, 5, 6-hexahydrobenzo [c] quinolizines
Petigara et al.	1974	Novel polycyclic heterocycles. XI. Synthesis of 11, 12‐dihydropyrido [2, 1‐b][1, 3] benzodiazepines, 6H‐pyrido [1, 2‐c][1, 3, 5] benzoxadiazepines, and 6H‐Pyrido [1, 2‐c][1, 3, 5] benzothiadiazepines
DE10017947A1 (de)	2001-10-25	Verfahren zur Herstellung benzo-annelierter Heterocyclen
Barbu et al.	2000	A Method for the synthesis of 3-methyl-2, 7-naphthyridine derivatives
NO165419B (no)	1990-10-29	Innretning for laasing og frigjoering av gjenstander beregnet for offentlig bruk, saasom bagasjetraller.
NO129744B (pt)	1974-05-20
Benington et al.	1960	Synthesis of Some Vicinal Trimethoxyphenyl Derivatives of Heterocyclic Nitrogen Bases
NO144099B (no)	1981-03-16	Dyse for maskinell flammehoevling av enkelte defekter paa overflaten til et metallegeme
AT262295B (de)	1968-06-10	Verfahren zur Herstellung von neuen Benzodiazepin-Derivaten und von deren Säureadditionssalzen
NO822445L (no)	1983-01-17	Fremgangsmaate ved fremstilling av 6-(3,6-dihydro-1(2h)-pyridyl)-pyrimidin-3-oksyder
NO126625B (pt)	1973-03-05
Lown	1969	Reaction of 3, 3-pentamethylenediaziridine with diphenylcyclopropenone
NO121040B (pt)	1971-01-11
DE2110534A1 (de)	1971-10-07	gamma-Piperazinobutyrophonderivate,Verfahren zu ihrer Herstellung und Arzneipraeparate
US20040116692A1 (en)	2004-06-17	Reductive alkylation of saturated cyclic amines