NO123223B - - Google Patents
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- Publication number
- NO123223B NO123223B NO3954/68A NO395468A NO123223B NO 123223 B NO123223 B NO 123223B NO 3954/68 A NO3954/68 A NO 3954/68A NO 395468 A NO395468 A NO 395468A NO 123223 B NO123223 B NO 123223B
- Authority
- NO
- Norway
- Prior art keywords
- benzodiazepine
- chloro
- phenyl
- methylamino
- mixture
- Prior art date
Links
- 238000001640 fractional crystallisation Methods 0.000 claims description 5
- YMPXMTJJHMOCFO-UHFFFAOYSA-N 7-chloro-4-hydroxy-n-methyl-5-phenyl-3,5-dihydro-1,4-benzodiazepin-2-amine Chemical compound ON1CC(NC)=NC2=CC=C(Cl)C=C2C1C1=CC=CC=C1 YMPXMTJJHMOCFO-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- RHUMXTALHSBJRL-UHFFFAOYSA-N 7-chloro-N-methyl-4-oxido-5-phenyl-1,5-dihydro-1,4-benzodiazepin-4-ium-2-imine Chemical compound CNC1=NC2=C(C=C(Cl)C=C2)C(C2=CC=CC=C2)[N+]([O-])=C1 RHUMXTALHSBJRL-UHFFFAOYSA-N 0.000 claims description 3
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 5
- 238000007254 oxidation reaction Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 229910019093 NaOCl Inorganic materials 0.000 description 4
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- BUCORZSTKDOEKQ-UHFFFAOYSA-N 7-chloro-4-hydroxy-N-methyl-5-phenyl-3H-1,4-benzodiazepin-2-imine Chemical group C=12C=C(Cl)C=CC2=NC(=NC)CN(O)C=1C1=CC=CC=C1 BUCORZSTKDOEKQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- XPAZAEVQMWOYMA-UHFFFAOYSA-N 4-oxido-5h-1,4-benzodiazepin-4-ium Chemical class C1[N+]([O-])=CC=NC2=CC=CC=C21 XPAZAEVQMWOYMA-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- -1 pyridine Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001624 sedative effect Effects 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
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK519867 | 1967-10-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO123223B true NO123223B (xx) | 1971-10-18 |
Family
ID=8140340
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO3954/68A NO123223B (xx) | 1967-10-19 | 1968-10-05 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3635949A (xx) |
| BE (1) | BE722561A (xx) |
| BR (1) | BR6802675D0 (xx) |
| CH (1) | CH503749A (xx) |
| DE (1) | DE1803911C3 (xx) |
| FR (1) | FR1594672A (xx) |
| GB (1) | GB1175649A (xx) |
| NL (1) | NL6814877A (xx) |
| NO (1) | NO123223B (xx) |
| SE (2) | SE363829B (xx) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102008012289A1 (de) | 2008-03-03 | 2009-09-10 | Anatolij Bolenko | Fotoreflektor und Fototapete |
-
1968
- 1968-09-16 US US760088A patent/US3635949A/en not_active Expired - Lifetime
- 1968-09-25 CH CH1431968A patent/CH503749A/de not_active IP Right Cessation
- 1968-09-27 BR BR202675/68A patent/BR6802675D0/pt unknown
- 1968-10-05 NO NO3954/68A patent/NO123223B/no unknown
- 1968-10-11 SE SE11517/71A patent/SE363829B/xx unknown
- 1968-10-11 SE SE13782/68A patent/SE352085B/xx unknown
- 1968-10-17 NL NL6814877A patent/NL6814877A/xx unknown
- 1968-10-18 GB GB49489/68A patent/GB1175649A/en not_active Expired
- 1968-10-18 BE BE722561D patent/BE722561A/xx unknown
- 1968-10-18 DE DE1803911A patent/DE1803911C3/de not_active Expired
- 1968-10-18 FR FR1594672D patent/FR1594672A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1175649A (en) | 1969-12-23 |
| DE1803911A1 (de) | 1969-10-02 |
| SE352085B (xx) | 1972-12-18 |
| FR1594672A (xx) | 1970-06-08 |
| BE722561A (xx) | 1969-04-01 |
| DE1803911B2 (de) | 1974-03-28 |
| SE363829B (xx) | 1974-02-04 |
| US3635949A (en) | 1972-01-18 |
| BR6802675D0 (pt) | 1973-04-17 |
| CH503749A (de) | 1971-02-28 |
| DE1803911C3 (de) | 1974-11-14 |
| NL6814877A (xx) | 1969-04-22 |
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