US3513159A - Method of producing 1,2-dihydro-1,4-benzodiazepines-2-ones - Google Patents
Method of producing 1,2-dihydro-1,4-benzodiazepines-2-ones Download PDFInfo
- Publication number
- US3513159A US3513159A US663499A US3513159DA US3513159A US 3513159 A US3513159 A US 3513159A US 663499 A US663499 A US 663499A US 3513159D A US3513159D A US 3513159DA US 3513159 A US3513159 A US 3513159A
- Authority
- US
- United States
- Prior art keywords
- dihydro
- producing
- benzodiazepines
- ones
- phenyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Lifetime
Links
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
Definitions
- the invention relates to a novel method of producing l-alky] 1,2 dihydro 3H 5 phenyl-1,4-benzodiazepin- 2-ones by oxidizing the corresponding 1,2,4,5-tetrahydro compounds with azodicarboxylic acid diethyl ester.
- This invention relates to a method of producing l-alkyl- 1,Z-dihydro-3H-2-oxo-5-phenyl-1,4-benzodiazepines of the general formula R2 f 1 XQ /C]EI2 I R (I) wherein X represents hydrogen, halogen, a nitro group, a nitroso group, an alkyl group, a trifluoromethyl group or a hydroxy group, R represents a phenyl group, which may be substituted, and R represents a lower alkyl group, preferably a methyl group.
- 1,4-benzodiazepines of the general formula ⁇ CH-NH R (II) wherein X and R are as hereinbefore described can be oxidized by means of common oxidizing agents, such as CrO to establish a double bond in the 4,5-position.
- reaction proceeds smoothly, swiftly, and completely quantitatively, which is a great advantage, because the purification problems are avoided, which are characteristic for the oxidation methods using common oxidizing agents as mentioned hereinbefore.
- the compounds resulting from the present method are of strongly sedative and tranquilizing effect.
- the present method is illustrated by the following example.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DK466266AA DK124260B (da) | 1966-09-09 | 1966-09-09 | Fremgangsmåde til fremstilling af 1-alkyl-1,2-dihydro-3H-2-oxo-5-fenyl-1,4-benzodiazepinforbindelser. |
Publications (1)
Publication Number | Publication Date |
---|---|
US3513159A true US3513159A (en) | 1970-05-19 |
Family
ID=8135555
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US663499A Expired - Lifetime US3513159A (en) | 1966-09-09 | 1967-08-28 | Method of producing 1,2-dihydro-1,4-benzodiazepines-2-ones |
Country Status (9)
Country | Link |
---|---|
US (1) | US3513159A (da) |
CH (1) | CH487907A (da) |
DE (1) | DE1645992A1 (da) |
DK (1) | DK124260B (da) |
ES (1) | ES344822A1 (da) |
FI (1) | FI47772C (da) |
NL (1) | NL6712101A (da) |
NO (1) | NO123180B (da) |
SE (1) | SE335988B (da) |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3371085A (en) * | 1959-12-10 | 1968-02-27 | Hoffmann La Roche | 5-aryl-3h-1,4-benzodiazepin-2(1h)-ones |
-
1966
- 1966-09-09 DK DK466266AA patent/DK124260B/da unknown
-
1967
- 1967-08-28 US US663499A patent/US3513159A/en not_active Expired - Lifetime
- 1967-08-30 FI FI672330A patent/FI47772C/fi active
- 1967-09-01 DE DE19671645992 patent/DE1645992A1/de active Pending
- 1967-09-04 NL NL6712101A patent/NL6712101A/xx unknown
- 1967-09-04 CH CH1235667A patent/CH487907A/de not_active IP Right Cessation
- 1967-09-05 NO NO169616A patent/NO123180B/no unknown
- 1967-09-06 SE SE12298/67A patent/SE335988B/xx unknown
- 1967-09-07 ES ES344822A patent/ES344822A1/es not_active Expired
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3371085A (en) * | 1959-12-10 | 1968-02-27 | Hoffmann La Roche | 5-aryl-3h-1,4-benzodiazepin-2(1h)-ones |
Also Published As
Publication number | Publication date |
---|---|
FI47772B (da) | 1973-11-30 |
SE335988B (da) | 1971-06-21 |
NL6712101A (da) | 1968-03-11 |
FI47772C (fi) | 1974-03-11 |
NO123180B (da) | 1971-10-11 |
DK124260B (da) | 1972-10-02 |
CH487907A (de) | 1970-03-31 |
ES344822A1 (es) | 1968-11-01 |
DE1645992A1 (de) | 1970-07-16 |
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