JPS5536403A - Preparation of 1-benzazonine derivative - Google Patents
Preparation of 1-benzazonine derivativeInfo
- Publication number
- JPS5536403A JPS5536403A JP9233678A JP9233678A JPS5536403A JP S5536403 A JPS5536403 A JP S5536403A JP 9233678 A JP9233678 A JP 9233678A JP 9233678 A JP9233678 A JP 9233678A JP S5536403 A JPS5536403 A JP S5536403A
- Authority
- JP
- Japan
- Prior art keywords
- benzazonine
- derivative
- optically active
- solvent
- methyl
- 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.)
- Granted
Links
- ASLUVGUEPYXPRF-UHFFFAOYSA-N 1h-1-benzazonine Chemical class N1C=CC=CC=CC2=CC=CC=C21 ASLUVGUEPYXPRF-UHFFFAOYSA-N 0.000 title 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 2
- 150000007524 organic acids Chemical class 0.000 abstract 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 abstract 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 abstract 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 abstract 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 abstract 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 abstract 1
- 230000004071 biological effect Effects 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 231100000053 low toxicity Toxicity 0.000 abstract 1
- 229960002510 mandelic acid Drugs 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 231100000957 no side effect Toxicity 0.000 abstract 1
- 235000002906 tartaric acid Nutrition 0.000 abstract 1
- 239000011975 tartaric acid Substances 0.000 abstract 1
Landscapes
- Other In-Based Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
PURPOSE: To obtain the title compound, a lenitive having no side effect, low toxicity and a high biological activity, by making use of the solubility difference of the diastereomeric mixture formed by treatment of a derivative of dl-benzazonine with an optically active organic acid in a solvent.
CONSTITUTION: A derivative of dl-benzazonine of the formula (R=H, methyl) is treated with an optically active organic acid (example; optically active mandelic acid, optically active tartaric acid, etc.) in a solvent to form diastereomeric mixture, form which a derivative of l-benzazonine is isolated by making use of the solubility difference of the isomers to a solvent, e.g. acetone, methyl ethyl ketone, methyl isobutyl ketone, etc.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9233678A JPS5536403A (en) | 1978-07-28 | 1978-07-28 | Preparation of 1-benzazonine derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9233678A JPS5536403A (en) | 1978-07-28 | 1978-07-28 | Preparation of 1-benzazonine derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5536403A true JPS5536403A (en) | 1980-03-14 |
| JPS6320817B2 JPS6320817B2 (en) | 1988-04-30 |
Family
ID=14051543
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9233678A Granted JPS5536403A (en) | 1978-07-28 | 1978-07-28 | Preparation of 1-benzazonine derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5536403A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57175010A (en) * | 1981-03-27 | 1982-10-27 | Mitsubishi Heavy Ind Ltd | Mandrel bar holding device |
| JPS5874206A (en) * | 1981-10-27 | 1983-05-04 | Sumitomo Metal Ind Ltd | Rolling installation for metallic pipe |
| JPS6192708A (en) * | 1984-10-12 | 1986-05-10 | Nippon Steel Corp | Mandrel drawing method in mandrel mill |
| JPH037251A (en) * | 1980-11-14 | 1991-01-14 | Eli Lilly & Co | Production of (-)-n-methyl-3-(2-methylphenoxy)- 3-phenylpropylamine |
| WO2017038656A1 (en) * | 2015-08-28 | 2017-03-09 | 日本臓器製薬株式会社 | Method for producing novel 4-benzazonine derivative |
-
1978
- 1978-07-28 JP JP9233678A patent/JPS5536403A/en active Granted
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH037251A (en) * | 1980-11-14 | 1991-01-14 | Eli Lilly & Co | Production of (-)-n-methyl-3-(2-methylphenoxy)- 3-phenylpropylamine |
| JPH046699B2 (en) * | 1980-11-14 | 1992-02-06 | Lilly Co Eli | |
| JPS57175010A (en) * | 1981-03-27 | 1982-10-27 | Mitsubishi Heavy Ind Ltd | Mandrel bar holding device |
| JPS5874206A (en) * | 1981-10-27 | 1983-05-04 | Sumitomo Metal Ind Ltd | Rolling installation for metallic pipe |
| JPS6192708A (en) * | 1984-10-12 | 1986-05-10 | Nippon Steel Corp | Mandrel drawing method in mandrel mill |
| WO2017038656A1 (en) * | 2015-08-28 | 2017-03-09 | 日本臓器製薬株式会社 | Method for producing novel 4-benzazonine derivative |
| JPWO2017038656A1 (en) * | 2015-08-28 | 2018-06-14 | 日本臓器製薬株式会社 | Method for producing novel 4-benzoazonin derivative |
| US10703725B2 (en) | 2015-08-28 | 2020-07-07 | Nippon Zoki Pharmaceutical Co., Ltd. | Process for producing novel 4-benzoazonine derivatives |
| JP2021098744A (en) * | 2015-08-28 | 2021-07-01 | 日本臓器製薬株式会社 | Method for producing novel 4-benzazonine derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6320817B2 (en) | 1988-04-30 |
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