NO742737L - - Google Patents

Info

Publication number: NO742737L
Authority: NO; Norway
Prior art keywords: formula; general formula; benzodiazepine; halogen; compound
Prior art date: 1973-07-27

Application number

NO742737A

Other languages

English (en)

Norwegian (no)

Inventor

D L Coffen

R I Fryer

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.)

1973-07-27

Filing date

1974-07-26

Publication date

1975-02-24

1974-07-26 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1975-02-24 Publication of NO742737L publication Critical patent/NO742737L/no

Links

150000001875 compounds Chemical class 0.000 claims description 13
238000000034 method Methods 0.000 claims description 11
229910052736 halogen Inorganic materials 0.000 claims description 10
150000002367 halogens Chemical class 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 2
VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
150000002431 hydrogen Chemical class 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
238000010992 reflux Methods 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
230000003647 oxidation Effects 0.000 description 6
238000007254 oxidation reaction Methods 0.000 description 6
239000002904 solvent Substances 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 5
239000000047 product Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical class N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 3
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
-1 methoxy, ethoxy, propoxy Chemical group 0.000 description 3
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
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 3
238000005406 washing Methods 0.000 description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
QQUIWIVTEWQHKA-UHFFFAOYSA-N 3h-1,4-benzodiazepine Chemical class C1=NCC=NC2=CC=CC=C21 QQUIWIVTEWQHKA-UHFFFAOYSA-N 0.000 description 2
YERSFONNQQBBRN-UHFFFAOYSA-N 7-chloro-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepine-2-carbonitrile Chemical compound ClC=1C=CC2=C(C(=NCC(N2)C#N)C2=CC=CC=C2)C1 YERSFONNQQBBRN-UHFFFAOYSA-N 0.000 description 2
JVQJIOGELLYIIQ-UHFFFAOYSA-N 7-chloro-5-phenyl-3H-1,4-benzodiazepine-2-carbonitrile Chemical compound C(#N)C1=NC2=C(C(=NC1)C1=CC=CC=C1)C=C(C=C2)Cl JVQJIOGELLYIIQ-UHFFFAOYSA-N 0.000 description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-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
OFLXLNCGODUUOT-UHFFFAOYSA-N acetohydrazide Chemical compound C\C(O)=N\N OFLXLNCGODUUOT-UHFFFAOYSA-N 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
229940049706 benzodiazepine Drugs 0.000 description 2
238000007333 cyanation reaction Methods 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
WPHGSKGZRAQSGP-UHFFFAOYSA-N methylenecyclohexane Natural products C1CCCC2CC21 WPHGSKGZRAQSGP-UHFFFAOYSA-N 0.000 description 2
230000000269 nucleophilic effect Effects 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000008096 xylene Substances 0.000 description 2
CZWUXUPLWLGPBZ-UHFFFAOYSA-N 1,3-dihydro-1,2-benzodiazepine-2-carbonitrile Chemical class C(#N)N1NC2=C(C=CC1)C=CC=C2 CZWUXUPLWLGPBZ-UHFFFAOYSA-N 0.000 description 1
NTLDJOUQLMVTMD-UHFFFAOYSA-N 1-phenyl-1,4-benzodiazepine Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C=NC=C1 NTLDJOUQLMVTMD-UHFFFAOYSA-N 0.000 description 1
GSIGZZKHXAAYOA-UHFFFAOYSA-N 6-phenyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical class C12=CC=CC=C2N2C=NN=C2CN=C1C1=CC=CC=C1 GSIGZZKHXAAYOA-UHFFFAOYSA-N 0.000 description 1
ZXBHWLWXRCXTSO-UHFFFAOYSA-N 7-chloro-5-(2-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine-2-carbonitrile Chemical compound ClC=1C=CC2=C(C(=NCC(N2)C#N)C2=C(C=CC=C2)F)C1 ZXBHWLWXRCXTSO-UHFFFAOYSA-N 0.000 description 1
VIYATZUINQZUAA-UHFFFAOYSA-N 7-chloro-5-(2-fluorophenyl)-2,3-dihydro-1h-1,4-benzodiazepine Chemical compound FC1=CC=CC=C1C1=NCCNC2=CC=C(Cl)C=C12 VIYATZUINQZUAA-UHFFFAOYSA-N 0.000 description 1
GIVYEEPCHMGCEK-UHFFFAOYSA-N 7-chloro-5-phenyl-3h-1,4-benzodiazepine Chemical compound C12=CC(Cl)=CC=C2N=CCN=C1C1=CC=CC=C1 GIVYEEPCHMGCEK-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
MPZVLJCMGPYWQQ-UHFFFAOYSA-N 8-chloro-6-(2-fluorophenyl)-1-methyl-4h-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1F MPZVLJCMGPYWQQ-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000001035 drying 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
239000000284 extract Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
DXGIRFAFSFKYCF-UHFFFAOYSA-N propanehydrazide Chemical compound CCC(=O)NN DXGIRFAFSFKYCF-UHFFFAOYSA-N 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229940125723 sedative agent Drugs 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
238000001665 trituration Methods 0.000 description 1

Classifications

- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO742737A 1973-07-27 1974-07-26 NO742737L (fi)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US00383363A US3849434A (en)	1973-07-27	1973-07-27	Process for preparing triazolobenzodiazepines

Publications (1)

Publication Number	Publication Date
NO742737L true NO742737L (fi)	1975-02-24

Family

ID=23512776

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO742737A NO742737L (fi)	1973-07-27	1974-07-26

Country Status (19)

Country	Link
US (1)	US3849434A (fi)
JP (1)	JPS5041891A (fi)
AR (1)	AR204535A1 (fi)
AU (1)	AU7169674A (fi)
BE (1)	BE818133A (fi)
DD (1)	DD114608A5 (fi)
DE (1)	DE2436148A1 (fi)
DK (1)	DK402874A (fi)
ES (1)	ES428640A1 (fi)
FI (1)	FI226074A (fi)
FR (1)	FR2270255B1 (fi)
GB (1)	GB1445789A (fi)
IL (1)	IL45343A0 (fi)
LU (1)	LU70604A1 (fi)
NL (1)	NL7410111A (fi)
NO (1)	NO742737L (fi)
PL (1)	PL89891B1 (fi)
SE (1)	SE7409735L (fi)
ZA (1)	ZA744605B (fi)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4075408A (en) *	1975-09-08	1978-02-21	Parke, Davis & Company	Imidazopyrazolodiazepine compounds
WO2007010369A2 (en) *	2005-07-22	2007-01-25	Emcure Pharmaceuticals Limited	Sustained release formulation of alprazolam

1973
- 1973-07-27 US US00383363A patent/US3849434A/en not_active Expired - Lifetime
1974
- 1974-01-01 AR AR254905A patent/AR204535A1/es active
- 1974-07-18 ZA ZA00744605A patent/ZA744605B/xx unknown
- 1974-07-25 DD DD180122A patent/DD114608A5/xx unknown
- 1974-07-25 IL IL45343A patent/IL45343A0/xx unknown
- 1974-07-25 JP JP49084703A patent/JPS5041891A/ja active Pending
- 1974-07-25 LU LU70604*A patent/LU70604A1/xx unknown
- 1974-07-25 FR FR7425867A patent/FR2270255B1/fr not_active Expired
- 1974-07-26 NO NO742737A patent/NO742737L/no unknown
- 1974-07-26 FI FI2260/74A patent/FI226074A/fi unknown
- 1974-07-26 BE BE146982A patent/BE818133A/xx unknown
- 1974-07-26 ES ES428640A patent/ES428640A1/es not_active Expired
- 1974-07-26 DE DE2436148A patent/DE2436148A1/de active Pending
- 1974-07-26 SE SE7409735A patent/SE7409735L/xx unknown
- 1974-07-26 AU AU71696/74A patent/AU7169674A/en not_active Expired
- 1974-07-26 NL NL7410111A patent/NL7410111A/xx unknown
- 1974-07-26 GB GB3316774A patent/GB1445789A/en not_active Expired
- 1974-07-26 DK DK402874A patent/DK402874A/da unknown
- 1974-07-26 PL PL1974173038A patent/PL89891B1/pl unknown

Also Published As

Publication number	Publication date
NL7410111A (nl)	1975-01-29
US3849434A (en)	1974-11-19
LU70604A1 (fi)	1976-05-31
BE818133A (fr)	1975-01-27
ES428640A1 (es)	1976-08-16
JPS5041891A (fi)	1975-04-16
AR204535A1 (es)	1976-02-12
AU7169674A (en)	1976-01-29
FR2270255B1 (fi)	1976-10-22
PL89891B1 (fi)	1976-12-31
IL45343A0 (en)	1974-10-22
ZA744605B (en)	1975-08-27
DE2436148A1 (de)	1975-02-13
FR2270255A1 (fi)	1975-12-05
DD114608A5 (fi)	1975-08-12
DK402874A (fi)	1975-04-01
SE7409735L (fi)	1975-01-28
GB1445789A (en)	1976-08-11
FI226074A (fi)	1975-01-28

Publication	Publication Date	Title
US3100770A (en)	1963-08-13	5-pyridyl-1,4-benzodiazepine compounds
NO170987B (no)	1992-09-28	Fremgangsmaate for avsvovling av jern
NO742737L (fi)	1975-02-24
Finch et al.	1971	Rearrangement of 3-amino-1-benzylindazole to 4-amino-2-phenylquinazoline
NO153263B (no)	1985-11-04	Lavtirriterende fast eller flytende saapepreparat
US3235555A (en)	1966-02-15	7-amino-3-cyanoethyl-1-methyl-2, 4-dioxo-1, 2, 3, 4, 5, 6-hexahydropyrido[2, 3-d] pyrimidine and related compounds
NO120370B (fi)	1970-10-12
Peet et al.	1977	Synthesis of 5H‐Tetrazolo [1, 5‐d][1, 4] benzodiazepin‐6 (7H) ones
DE1695161A1 (de)	1970-12-10	Verfahren zur Herstellung von Benzodiazepin-Derivaten
US4247463A (en)	1981-01-27	Process for the preparation of imidazobenzodiazepines
NO166536B (no)	1991-04-29	Flammehemmende fenolskum og fremgangsmaate for dets fremstilling.
DE1965980A1 (de)	1971-01-07	2-(Dioxopiperazino)-benzophenone und Verfahren zu ihrer Herstellung
DE1288610B (de)	1969-02-06	Verfahren zur Herstellung von 2-Oxo-1, 2-dihydro-3H-1, 4-benzodiazepinen
EP0072029B1 (de)	1986-10-22	Triazolobenzazepine, Verfahren und Zwischenprodukte zu deren Herstellung und diese enthaltende Arzneimittel
KR840002269B1 (ko)	1984-12-14	이미다조 벤조디아제핀 유도체의 제조방법
NO132800B (fi)	1975-09-29
US3153082A (en)	1964-10-13	2-amino-benzophenones
NO128328B (fi)	1973-10-29
US3321520A (en)	1967-05-23	Iminocycloheptatrienes and a process for preparing the same
US3413346A (en)	1968-11-26	2-(2-haloethylamino)-5-halo-benzophenones
US3904603A (en)	1975-09-09	2,3,4,5-tetrahydro-4,4-dialkyl-1h-1,4-benzodiazepine halides
US3838116A (en)	1974-09-24	Process for preparing 1,4-benzodiazepines
US4250095A (en)	1981-02-10	Imidazobenzodiazepines
US3671517A (en)	1972-06-20	Preparation of 2,3,4,5-tetrahydro-5-phen-yl-1h-1,4-benzodiazepines and intermediates
US3906025A (en)	1975-09-16	(2-Aminobenzophenone) acetonitriles