JPS56115751A - Preparation of novel 3-acylamino-4-hydroxy-alpha- aralkylaminomethyl benzyl alcohol - Google Patents
Preparation of novel 3-acylamino-4-hydroxy-alpha- aralkylaminomethyl benzyl alcoholInfo
- Publication number
- JPS56115751A JPS56115751A JP7870080A JP7870080A JPS56115751A JP S56115751 A JPS56115751 A JP S56115751A JP 7870080 A JP7870080 A JP 7870080A JP 7870080 A JP7870080 A JP 7870080A JP S56115751 A JPS56115751 A JP S56115751A
- Authority
- JP
- Japan
- Prior art keywords
- benzyl alcohol
- formula
- benzyl
- hydroxy
- novel
- 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
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 title abstract 10
- 235000019445 benzyl alcohol Nutrition 0.000 title abstract 4
- -1 3-Formylamino-4-hydroxy-α-[ N-( 1-methyl-2-p-hydroxyphenylethyl ) aminomethyl ]benzyl Chemical group 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 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 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- 210000000056 organ Anatomy 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 230000000241 respiratory effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 210000002460 smooth muscle Anatomy 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
NEW MATERIAL:The titled benzyl alcohol (acid addition salt) expressed by formula I.
EXAMPLE: 3-Formylamino-4-hydroxy-α-[ N-( 1-methyl-2-p-hydroxyphenylethyl ) aminomethyl ]benzyl alcohol.
USE: A bronchodiator having an activity in a respiratory organ smooth muscle.
PROCESS: A compound of formula II [A and D are H or benzyl; B is carbonyl or formula III; E is branched lower alkylene; R1 is (substituted) acyl; R2 is phenyl substituted by lower alkyl, OH, etc.; however, B is carbonyl when A and D are both H], e.g. 4-benzyloxy-3-formylamino-α-[N-benzyl-N-(1-methyl-2-p-hydroxyphenylethyl)aminomethyl]benzyl alcohol, is catalytically reduced in water or an organic solvent, e.g. an alcohol, in the presence of a palladium catalyst to give the exemplified compound. The starting compound of formula II is also a novel substance.
COPYRIGHT: (C)1981,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55078700A JPS599542B2 (en) | 1980-06-11 | 1980-06-11 | Novel method for producing 3-acylamino-4-hydroxy-α-(aralkyl aminomethyl)benzyl alcohol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55078700A JPS599542B2 (en) | 1980-06-11 | 1980-06-11 | Novel method for producing 3-acylamino-4-hydroxy-α-(aralkyl aminomethyl)benzyl alcohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56115751A true JPS56115751A (en) | 1981-09-11 |
| JPS599542B2 JPS599542B2 (en) | 1984-03-03 |
Family
ID=13669138
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55078700A Expired JPS599542B2 (en) | 1980-06-11 | 1980-06-11 | Novel method for producing 3-acylamino-4-hydroxy-α-(aralkyl aminomethyl)benzyl alcohol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS599542B2 (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009032764A1 (en) | 2007-08-28 | 2009-03-12 | Sepracor Inc. | Acetamide stereoisomer |
| JP2010538009A (en) * | 2007-08-28 | 2010-12-09 | セプラコール インク． | Carbamate stereoisomers |
| CN103896795A (en) * | 2012-12-26 | 2014-07-02 | 上海医药工业研究院 | Methanamide compound, preparation method of intermediate of methanamide compound, and applications of the intermediate |
| CN109535027A (en) * | 2018-11-28 | 2019-03-29 | 广州健康元呼吸药物工程技术有限公司 | A kind of preparation method of formoterol, its pharmaceutically acceptable salt and its intermediate |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60235432A (en) * | 1984-05-09 | 1985-11-22 | Toshiba Corp | Wire bonding apparatus |
-
1980
- 1980-06-11 JP JP55078700A patent/JPS599542B2/en not_active Expired
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009032764A1 (en) | 2007-08-28 | 2009-03-12 | Sepracor Inc. | Acetamide stereoisomer |
| JP2010538010A (en) * | 2007-08-28 | 2010-12-09 | セプラコール インク． | Acetamide stereoisomer |
| JP2010538009A (en) * | 2007-08-28 | 2010-12-09 | セプラコール インク． | Carbamate stereoisomers |
| US8501994B2 (en) * | 2007-08-28 | 2013-08-06 | Sunovion Pharmaceuticals Inc. | Acetamide stereoisomer |
| US8664441B2 (en) | 2007-08-28 | 2014-03-04 | Sunovion Pharmaceuticals Inc. | Acetamide stereoisomer |
| KR101398775B1 (en) * | 2007-08-28 | 2014-05-27 | 선오비온 파마슈티컬스 인코포레이티드 | Acetamide stereoisomer |
| US9040588B2 (en) | 2007-08-28 | 2015-05-26 | Sunovion Pharmaceuticals Inc. | Acetamide stereoisomer |
| US9499476B2 (en) | 2007-08-28 | 2016-11-22 | Sunovion Pharmaceuticals Inc. | Acetamide stereoisomer |
| CN103896795A (en) * | 2012-12-26 | 2014-07-02 | 上海医药工业研究院 | Methanamide compound, preparation method of intermediate of methanamide compound, and applications of the intermediate |
| CN103896795B (en) * | 2012-12-26 | 2016-01-06 | 上海医药工业研究院 | The preparation method and its usage of benzamide compound, its intermediate |
| CN109535027A (en) * | 2018-11-28 | 2019-03-29 | 广州健康元呼吸药物工程技术有限公司 | A kind of preparation method of formoterol, its pharmaceutically acceptable salt and its intermediate |
| CN109535027B (en) * | 2018-11-28 | 2021-12-21 | 广州健康元呼吸药物工程技术有限公司 | Preparation method of formoterol, medicinal salt and intermediate thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS599542B2 (en) | 1984-03-03 |
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