NO118910B - - Google Patents

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Publication number: NO118910B
Authority: NO; Norway
Prior art keywords: general formula; reaction; formula; above meaning; lower alkyl
Prior art date: 1963-10-29

Application number

NO155319A

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.)

1963-10-29

Filing date

1964-10-27

Publication date

1970-03-02

1964-10-27 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1970-03-02 Publication of NO118910B publication Critical patent/NO118910B/no

Links

238000000034 method Methods 0.000 claims description 10
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims description 4
239000003513 alkali Substances 0.000 claims description 3
150000001342 alkaline earth metals Chemical class 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens 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
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 7
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
239000000203 mixture Substances 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 3
239000007789 gas Substances 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000002844 melting Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
238000010992 reflux Methods 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
MTNWQRGOHOXCFV-UHFFFAOYSA-N 7-chloro-2-methoxy-4-oxido-5-phenyl-3h-1,4-benzodiazepin-4-ium Chemical compound [O-][N+]=1CC(OC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 MTNWQRGOHOXCFV-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-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
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
125000003342 alkenyl group Chemical group 0.000 description 2
150000001557 benzodiazepines Chemical class 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
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
239000006260 foam Substances 0.000 description 2
238000002955 isolation Methods 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
LNJIWXQSXIDEAO-UHFFFAOYSA-N 4-oxido-5-phenyl-5H-1,4-benzodiazepin-4-ium Chemical class C1(=CC=CC=C1)C1[N+](=CC=NC2=C1C=CC=C2)[O-] LNJIWXQSXIDEAO-UHFFFAOYSA-N 0.000 description 1
KFDNKXWSTFABQT-UHFFFAOYSA-N 6-chloro-2-(chloromethyl)-3-oxido-4-phenylquinazolin-3-ium Chemical compound [O-][N+]1=C(CCl)N=C2C=CC(Cl)=CC2=C1C1=CC=CC=C1 KFDNKXWSTFABQT-UHFFFAOYSA-N 0.000 description 1
BUCORZSTKDOEKQ-UHFFFAOYSA-N 7-chloro-4-hydroxy-N-methyl-5-phenyl-3H-1,4-benzodiazepin-2-imine Chemical compound C=12C=C(Cl)C=CC2=NC(=NC)CN(O)C=1C1=CC=CC=C1 BUCORZSTKDOEKQ-UHFFFAOYSA-N 0.000 description 1
DQZUAVXXQQOPOW-UHFFFAOYSA-N 7-chloro-n,n-dimethyl-4-oxido-5-phenyl-3h-1,4-benzodiazepin-4-ium-2-amine Chemical compound [O-][N+]=1CC(N(C)C)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 DQZUAVXXQQOPOW-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
229940049706 benzodiazepine Drugs 0.000 description 1
230000000694 effects Effects 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
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
-1 lower alkanols Chemical class 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000005394 methallyl group Chemical group 0.000 description 1
ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
239000000932 sedative agent Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 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
- C07D243/20—Nitrogen atoms
- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/24—Oxygen atoms

Landscapes

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

NO155319A 1963-10-29 1964-10-27 NO118910B (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US319673A US3312688A (en)	1963-10-29	1963-10-29	Process for preparing 2-aminobenzodiazepines

Publications (1)

Publication Number	Publication Date
NO118910B true NO118910B (fr)	1970-03-02

Family

ID=23243220

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO155319A NO118910B (fr)	1963-10-29	1964-10-27

Country Status (14)

Country	Link
US (1)	US3312688A (fr)
BE (1)	BE654924A (fr)
BR (1)	BR6463736D0 (fr)
CH (1)	CH443319A (fr)
DE (2)	DE1445910A1 (fr)
DK (1)	DK114271B (fr)
ES (1)	ES305413A1 (fr)
FR (1)	FR1442311A (fr)
GB (1)	GB1058739A (fr)
IL (1)	IL22192A (fr)
NL (3)	NL139527B (fr)
NO (1)	NO118910B (fr)
OA (1)	OA00943A (fr)
SE (2)	SE329625B (fr)

1963
- 1963-10-29 US US319673A patent/US3312688A/en not_active Expired - Lifetime
1964
- 1964-09-30 CH CH1272964A patent/CH443319A/de unknown
- 1964-10-03 DE DE19641445910 patent/DE1445910A1/de active Pending
- 1964-10-03 DE DE19641695217 patent/DE1695217A1/de active Pending
- 1964-10-05 IL IL22192A patent/IL22192A/en unknown
- 1964-10-19 DK DK516164AA patent/DK114271B/da unknown
- 1964-10-22 GB GB43160/64A patent/GB1058739A/en not_active Expired
- 1964-10-26 FR FR992633A patent/FR1442311A/fr not_active Expired
- 1964-10-27 NO NO155319A patent/NO118910B/no unknown
- 1964-10-27 BR BR163736/64A patent/BR6463736D0/pt unknown
- 1964-10-27 NL NL646412484A patent/NL139527B/xx not_active IP Right Cessation
- 1964-10-28 ES ES0305413A patent/ES305413A1/es not_active Expired
- 1964-10-28 BE BE654924D patent/BE654924A/xx unknown
- 1964-10-29 SE SE13019/64A patent/SE329625B/xx unknown
- 1964-10-29 SE SE10586/70A patent/SE355580B/xx unknown
- 1964-12-26 OA OA51038A patent/OA00943A/fr unknown
1971
- 1971-11-15 NL NL7115681A patent/NL7115681A/xx unknown
- 1971-11-15 NL NL7115680A patent/NL7115680A/xx unknown

Also Published As

Publication number	Publication date
FR1442311A (fr)	1966-06-17
US3312688A (en)	1967-04-04
DK114271B (da)	1969-06-16
NL7115680A (fr)	1972-02-25
SE329625B (fr)	1970-10-19
NL7115681A (fr)	1972-02-25
GB1058739A (en)	1967-02-15
DE1445910A1 (de)	1969-01-23
BE654924A (fr)	1965-04-28
DE1695217A1 (de)	1972-02-17
IL22192A (en)	1968-01-25
NL139527B (nl)	1973-08-15
BR6463736D0 (pt)	1973-07-17
ES305413A1 (es)	1965-05-01
NL6412484A (fr)	1965-05-03
CH443319A (de)	1967-09-15
SE355580B (fr)	1973-04-30
OA00943A (fr)	1968-03-22

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