NO121040B - - Google Patents

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Publication number: NO121040B
Authority: NO; Norway
Prior art keywords: formula; compounds; mixture; glycine; hours
Prior art date: 1964-10-01

Application number

NO159921A

Other languages

English (en)

Norwegian (no)

Inventor

G Archer

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.)

1964-10-01

Filing date

1965-09-30

Publication date

1971-01-11

1965-09-30 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1971-01-11 Publication of NO121040B publication Critical patent/NO121040B/no

Links

150000001875 compounds Chemical class 0.000 claims description 34
238000000034 method Methods 0.000 claims description 11
238000009833 condensation Methods 0.000 claims description 10
230000005494 condensation Effects 0.000 claims description 10
239000004471 Glycine Substances 0.000 claims description 8
229910052736 halogen Inorganic materials 0.000 claims description 7
150000002367 halogens Chemical class 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
239000007858 starting material Substances 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
239000000203 mixture Substances 0.000 description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 17
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical class NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
238000010992 reflux Methods 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 11
150000002148 esters Chemical class 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
238000001953 recrystallisation Methods 0.000 description 9
239000002253 acid Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 8
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
-1 methoxy, ethoxy Chemical group 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
150000001408 amides Chemical class 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
150000002923 oximes Chemical class 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
229910052794 bromium Inorganic materials 0.000 description 4
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 4
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 4
230000000694 effects Effects 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
239000000155 melt Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000002168 alkylating agent Substances 0.000 description 3
229940100198 alkylating agent Drugs 0.000 description 3
239000007795 chemical reaction product Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000000460 chlorine Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012043 crude product Substances 0.000 description 3
230000018044 dehydration Effects 0.000 description 3
238000006297 dehydration reaction Methods 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
238000000605 extraction Methods 0.000 description 3
235000013905 glycine and its sodium salt Nutrition 0.000 description 3
229930195733 hydrocarbon Natural products 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
125000001424 substituent group Chemical group 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
239000008096 xylene 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
HRPHZUAPQWJPCZ-UHFFFAOYSA-N (2-chloro-5-nitrophenyl)-phenylmethanone Chemical compound [O-][N+](=O)C1=CC=C(Cl)C(C(=O)C=2C=CC=CC=2)=C1 HRPHZUAPQWJPCZ-UHFFFAOYSA-N 0.000 description 2
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 2
RJUHASYVQSZHFA-UHFFFAOYSA-N 2-(2-benzoylanilino)acetic acid Chemical class OC(=O)CNC1=CC=CC=C1C(=O)C1=CC=CC=C1 RJUHASYVQSZHFA-UHFFFAOYSA-N 0.000 description 2
JUIKUQOUMZUFQT-UHFFFAOYSA-N 2-bromoacetamide Chemical class NC(=O)CBr JUIKUQOUMZUFQT-UHFFFAOYSA-N 0.000 description 2
SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
229940125681 anticonvulsant agent Drugs 0.000 description 2
239000001961 anticonvulsive agent Substances 0.000 description 2
229940049706 benzodiazepine Drugs 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical class NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 description 2
125000000623 heterocyclic group Chemical group 0.000 description 2
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
239000000725 suspension Substances 0.000 description 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
PZPZDEIASIKHPY-UHFFFAOYSA-N (2-amino-5-nitrophenyl)-phenylmethanone Chemical compound NC1=CC=C([N+]([O-])=O)C=C1C(=O)C1=CC=CC=C1 PZPZDEIASIKHPY-UHFFFAOYSA-N 0.000 description 1
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
ZHYMGSPDEVXULU-UHFFFAOYSA-N 1,2-benzodiazepin-3-one Chemical compound N1=NC(=O)C=CC2=CC=CC=C21 ZHYMGSPDEVXULU-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-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
108010077895 Sarcosine Proteins 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
239000011260 aqueous acid Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
239000012965 benzophenone Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000001804 chlorine Chemical class 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000002576 diazepinyl group Chemical class N1N=C(C=CC=C1)* 0.000 description 1
VMFYDQSRUVTFAA-UHFFFAOYSA-N dichloromethane ethanol hexane methanol Chemical compound CCCCCC.C(C)O.CO.C(Cl)Cl VMFYDQSRUVTFAA-UHFFFAOYSA-N 0.000 description 1
UPPBZOFWXKFRHI-UHFFFAOYSA-N dichloromethane;hexane;methanol Chemical compound OC.ClCCl.CCCCCC UPPBZOFWXKFRHI-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000006260 foam Substances 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003951 lactams Chemical group 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
230000007721 medicinal effect Effects 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000006396 nitration reaction Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
235000011056 potassium acetate Nutrition 0.000 description 1
150000003140 primary amides Chemical class 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000000523 sample Substances 0.000 description 1
229940043230 sarcosine Drugs 0.000 description 1
150000003334 secondary amides Chemical class 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
150000003511 tertiary amides Chemical class 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
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- 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

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

NO159921A 1964-10-01 1965-09-30 NO121040B (cs)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US400891A US3317518A (en)	1964-10-01	1964-10-01	Novel 5-aryl-1, 2, 4, 5-tetrahydrobenzo-diazepin-3-one compounds
US60414166A	1966-12-23	1966-12-23
US60414266A	1966-12-23	1966-12-23
US60414866A	1966-12-23	1966-12-23

Publications (1)

Publication Number	Publication Date
NO121040B true NO121040B (cs)	1971-01-11

Family

ID=27503456

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO159921A NO121040B (cs)	1964-10-01	1965-09-30

Country Status (11)

Country	Link
US (4)	US3317518A (cs)
BE (1)	BE670394A (cs)
BR (1)	BR6573560D0 (cs)
CH (1)	CH484162A (cs)
DE (4)	DE1543654A1 (cs)
FR (1)	FR5206M (cs)
GB (4)	GB1081636A (cs)
IL (1)	IL24380A (cs)
NL (1)	NL6512775A (cs)
NO (1)	NO121040B (cs)
SE (1)	SE330177B (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3997591A (en) *	1975-03-11	1976-12-14	Hoffmann-La Roche Inc.	Tricyclic benzodiazepines
GB9507661D0 (en) *	1995-04-13	1995-05-31	Ass Octel	Process

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3182054A (en) *		1965-05-04		Benzodiazepine - compounds
US3121074A (en) *		1964-02-11		Nitro substituted jh-l
US3121103A (en) *	1961-10-20	1964-02-11	Hoffmann La Roche	Aminobenzophenones
US3186996A (en) *	1961-10-30	1965-06-01	Nihon Surfactant Ind Co Ltd	Pyridoxine 3, 4-diacylates and their preparation
US3182065A (en) *	1964-04-09	1965-05-04	Hoffmann La Roche	2-acetamidobenzoyl-pyridines
US3182066A (en) *	1964-04-09	1965-05-04	Hoffmann La Roche	Aminophenyl-pyridyl ketones
US3182067A (en) *	1964-04-09	1965-05-04	Hoffmann La Roche	Benzodiazepine compounds

1964
- 1964-10-01 US US400891A patent/US3317518A/en not_active Expired - Lifetime
1965
- 1965-09-24 CH CH1323865A patent/CH484162A/de not_active IP Right Cessation
- 1965-09-28 DE DE19651543654 patent/DE1543654A1/de active Pending
- 1965-09-28 DE DE19651545965 patent/DE1545965A1/de active Pending
- 1965-09-29 GB GB28464/66A patent/GB1081636A/en not_active Expired
- 1965-09-29 GB GB28465/66A patent/GB1081637A/en not_active Expired
- 1965-09-29 GB GB41353/65A patent/GB1081634A/en not_active Expired
- 1965-09-29 BR BR173560/65A patent/BR6573560D0/pt unknown
- 1965-09-29 IL IL24380A patent/IL24380A/xx unknown
- 1965-09-29 GB GB28463/66A patent/GB1081635A/en not_active Expired
- 1965-09-30 NO NO159921A patent/NO121040B/no unknown
- 1965-09-30 FR FR33195A patent/FR5206M/fr not_active Expired
- 1965-10-01 NL NL6512775A patent/NL6512775A/xx unknown
- 1965-10-01 SE SE12776/65A patent/SE330177B/xx unknown
- 1965-10-01 BE BE670394D patent/BE670394A/xx unknown
- 1965-10-06 DE DE19651543655 patent/DE1543655A1/de active Pending
- 1965-10-06 DE DE19651695143 patent/DE1695143A1/de active Pending
1966
- 1966-12-23 US US604141A patent/US3504013A/en not_active Expired - Lifetime
- 1966-12-23 US US604148A patent/US3504015A/en not_active Expired - Lifetime
- 1966-12-23 US US604142A patent/US3504014A/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
CH484162A (de)	1970-01-15
GB1081635A (en)	1967-08-31
US3504015A (en)	1970-03-31
US3504013A (en)	1970-03-31
DE1543655A1 (de)	1969-10-02
GB1081637A (en)	1967-08-31
DE1695143A1 (de)	1970-02-12
NL6512775A (cs)	1966-04-04
US3317518A (en)	1967-05-02
BR6573560D0 (pt)	1973-08-02
IL24380A (en)	1969-05-28
BE670394A (cs)	1966-04-01
FR5206M (cs)	1967-07-03
GB1081634A (en)	1967-08-31
DE1545965A1 (de)	1969-12-11
DE1543654A1 (de)	1970-03-19
US3504014A (en)	1970-03-31
SE330177B (cs)	1970-11-09
GB1081636A (en)	1967-08-31

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Sternbach et al.	1962	Quinazolines and 1, 4-Benzodiazepines. VI. 1a Halo-, Methyl-, and Methoxy-substituted 1, 3-Dihydro-5-phenyl-2H-1, 4-benzodiazepin-2-ones1b, c
US4880810A (en)	1989-11-14	Quinazolinediones and pyridopyrimidinediones
SE452459B (sv)	1987-11-30	Indol-5-metansulfonamid, en farmaceutisk komposition och ett forfarande for framstellning av foreningen
NO162977B (no)	1989-12-04	Filt for fremstilling av en vaatpressefilt for en papirmaskin, samt fremgangsmaate ved fremstilling derav.
FI60010C (fi)	1981-11-10	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 4-(2-imidazolin-2-ylamino)-2,1,3-bensotiadiazoler
DK159148B (da)	1990-09-10	Analogifremgangsmaade til fremstilling af tranexamsyrederivater
US3466274A (en)	1969-09-09	Fluoreno-(1,9-ef)-1,4-diazepine-1-oxides and 1,3-diazafluoranthene-1-oxides
NO152064B (no)	1985-04-15	Utvidet stiveranordning for en selvreisende vinge
US4404214A (en)	1983-09-13	2-Pyridinecarboxamide derivatives compositions containing same and method of using same
NO121040B (cs)	1971-01-11
EP0118564B1 (en)	1987-04-22	4-amino-tetrahydro-2-naphthoic acid derivatives
WO1988001270A1 (en)	1988-02-25	Pyridopyrimidinediones
US2987518A (en)	1961-06-06	Certain 1h [4, 5-c]-imidazopyridines
US3531467A (en)	1970-09-29	Process for the preparation of 2,3,4,5-tetrahydro - 5 - aryl - 1h - 1,4 - benzodiazepine derivatives
NO121951B (cs)	1971-05-03
NO119593B (cs)	1970-06-08
FI70408B (fi)	1986-03-27	Foerfarande foer framstaellning av terapeutiskt aktiva karbostyrilderivat
Kaye	1949	2-Lepidyl substituted diamines
US3946018A (en)	1976-03-23	1,4-Dihydro-3 (2H)-isoquinolinone derivatives
CN112062763A (zh)	2020-12-11	羟基吡啶酮并[1,2-b][1,2,5]三氮卓平衍生物及制备和应用
US3974169A (en)	1976-08-10	α-[2-(2-Pyridyl)ethylamino]phenylacetic acid dihydrochloride Hemihydrate
NO129744B (cs)	1974-05-20
US3517061A (en)	1970-06-23	5h-1,4-benzodiazepin-5-ones
Brill et al.	1963	Quinoxaline Studies. XI. Unequivocal Syntheses of cis-and trans-dl-Decahydroquinoxalines. Resolution of trans-dl-Decahydroquinoxalines1-3
US3691176A (en)	1972-09-12	1-(4-fluorophenoxypropyl)-4-anilino-piperidines