ES2000382A6 - Production of substituted phenethylamine derivative - Google Patents
Production of substituted phenethylamine derivativeInfo
- Publication number
- ES2000382A6 ES2000382A6 ES8600685A ES8600685A ES2000382A6 ES 2000382 A6 ES2000382 A6 ES 2000382A6 ES 8600685 A ES8600685 A ES 8600685A ES 8600685 A ES8600685 A ES 8600685A ES 2000382 A6 ES2000382 A6 ES 2000382A6
- Authority
- ES
- Spain
- Prior art keywords
- formula
- reduced
- deriv
- phenethylamine
- aminopropyl
- 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
Links
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 title abstract 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 229940117803 phenethylamine Drugs 0.000 abstract 2
- XFFILAFLGDUMBF-UHFFFAOYSA-N 2-phenoxyacetaldehyde Chemical class O=CCOC1=CC=CC=C1 XFFILAFLGDUMBF-UHFFFAOYSA-N 0.000 abstract 1
- IORITYIZDHJCGT-SSDOTTSWSA-N 5-[(2r)-2-aminopropyl]-2-methoxybenzenesulfonamide Chemical compound COC1=CC=C(C[C@@H](C)N)C=C1S(N)(=O)=O IORITYIZDHJCGT-SSDOTTSWSA-N 0.000 abstract 1
- 239000012448 Lithium borohydride Substances 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- 229910052987 metal hydride Inorganic materials 0.000 abstract 1
- 150000004681 metal hydrides Chemical class 0.000 abstract 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 abstract 1
- 229910003446 platinum oxide Inorganic materials 0.000 abstract 1
- 239000012279 sodium borohydride Substances 0.000 abstract 1
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A phenethylamine deriv. of formula (I) is reacted with a substituted phenoxyacetaldehyde of formula (II) and the resulting intermediate is reduced to obtain a substd. phenethylamine deriv. of formula (III) (where R1 is lower alkoxy; R2 is lower alkyl; R3 is lower alkoxy). - (I) is pref. R(-)-5-(2 aminopropyl) 2-methoxybenzenesulfonamide or R(+)-5-(2-aminopropyl) 2-methoxy benzeneulfonamide. The reaction of (I) and (II) is effected in an inert solvent (methanol, ether, benzene at room temp. or under heat. After isolation, the intermediate is reduced by catalytic redn. in the presence of a catalyst of platinum oxide, Pd/C or Raney nickel, or reduced with a metal hydride such as sodium borohydride, lithium borohydride or lithium aluminium hydride.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP60254326A JPS62114952A (en) | 1985-11-13 | 1985-11-13 | Production of substituted phenethylamine derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2000382A6 true ES2000382A6 (en) | 1988-02-16 |
Family
ID=17263445
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES8600685A Expired ES2000382A6 (en) | 1985-11-13 | 1986-07-29 | Production of substituted phenethylamine derivative |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS62114952A (en) |
| KR (1) | KR940007746B1 (en) |
| AT (1) | AT397960B (en) |
| CA (1) | CA1282077C (en) |
| ES (1) | ES2000382A6 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2200699A1 (en) * | 2002-07-12 | 2004-03-01 | Ragactives Sl | Method of separating r(-)- and s(+)-5- 2- 2-(2-ethoxyphenoxy)ethyl amino propyl-2-methoxybenzene-sulphonamide |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4971990A (en) * | 1988-02-19 | 1990-11-20 | Hokuriku Pharmaceutical Co., Ltd. | Phenoxyethylamine derivatives, for preparing the same and composition for exhibiting excellent α1 -blocking activity containing the same |
| US5288759A (en) * | 1992-08-27 | 1994-02-22 | Alcon Laboratories, Inc. | Use of certain sulfamoyl-substituted phenethylamine derivatives to reverse drug-induced mydriasis |
| TW536402B (en) | 1998-06-26 | 2003-06-11 | Yamanouchi Pharma Co Ltd | Pharmaceutical composition for the therapy of voiding dysfunction |
| KR100525493B1 (en) | 2001-02-23 | 2005-11-02 | 연성정밀화학(주) | Process for preparing sulfamoyl-substituted phenethylamine derivatives |
| CZ291802B6 (en) * | 2001-10-25 | 2003-05-14 | Léčiva, A.S. | Process for preparing (R)-(-)-5-[2-[2-(2-ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzene sulfonamide |
| WO2004016582A1 (en) * | 2002-08-14 | 2004-02-26 | Natco Pharma Limited | An improved process for the preparation of tamsulosin hydrochloride |
| KR100503639B1 (en) | 2003-02-12 | 2005-07-26 | 보령제약 주식회사 | A purification process of Tamsulosin |
| JP2007513943A (en) | 2003-12-09 | 2007-05-31 | シージェイ コーポレーション | Process for the preparation of optically pure phenethylamine derivatives |
| SI21656A (en) * | 2003-12-29 | 2005-06-30 | LEK farmacevtska družba d.d. | Preparation of (r)-5-(2-(2-(2-ethoxyphenoxy)ethylamino)-1-propyl)-2-methoxybenzene sulphonamide hydrochloride of high chemical purity |
| SI21655A (en) * | 2003-12-29 | 2005-06-30 | LEK farmacevtska dru�ba d.d. | Synthesis of optically pure (r)-5-(2-aminopropyl)-methoxybenzene sulphonamide |
| CZ2004197A3 (en) | 2004-02-05 | 2005-08-17 | Zentiva, A. S. | Process for preparing (R)-(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide |
| US20080033208A1 (en) * | 2004-02-23 | 2008-02-07 | Dilipkumar Chandubhai Ramolia | Process for Manufacturing Optically Pure (R) or (S)-5-(2-Aminopropyl)-2-Methoxybenzene Sulfonamide |
| JP4800213B2 (en) * | 2004-07-07 | 2011-10-26 | 浜理薬品工業株式会社 | Process for producing optically active phenylpropylamine derivatives |
| CN100545148C (en) | 2004-08-16 | 2009-09-30 | 神隆新加坡私人有限公司 | Method for synthesizing tamsulosin medicine for resisting benign prostatic hyperplasia |
| US8273918B2 (en) | 2005-09-12 | 2012-09-25 | Avrobindo Pharma Ltd. | Process for preparing tamsulosin hydrochloride |
| WO2008152653A2 (en) * | 2007-06-11 | 2008-12-18 | Matrix Laboratories Ltd | An improved process for the preparation of tamsulosin hydrochloride |
| HUE029638T2 (en) | 2009-02-04 | 2017-03-28 | Astellas Pharma Inc | Pharmaceutical composition for oral administration |
| EP2255793A1 (en) | 2009-05-28 | 2010-12-01 | Krka Tovarna Zdravil, D.D., Novo Mesto | Pharmaceutical composition comprising tamsulosin |
| JP5661773B2 (en) * | 2009-09-12 | 2015-01-28 | サンド・アクチエンゲゼルシヤフト | Process for the preparation of indoline derivatives and intermediates thereof |
| DE202023102187U1 (en) | 2023-04-25 | 2023-05-02 | Nusrath Anjum | Derivative formulation based on tamsulosin |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1147342A (en) * | 1977-10-12 | 1983-05-31 | Kazuo Imai | Process of producing novel phenylethanolamine derivatives |
| US4558156A (en) * | 1980-02-08 | 1985-12-10 | Yamanouchi Pharmaceutical Co., Ltd. | Sulfamoyl-substituted phenethylamine derivatives |
| JPS56110665A (en) * | 1980-02-08 | 1981-09-01 | Yamanouchi Pharmaceut Co Ltd | Sulfamoyl-substituted phenetylamine derivative and its preparation |
-
1985
- 1985-11-13 JP JP60254326A patent/JPS62114952A/en active Granted
-
1986
- 1986-07-07 KR KR1019860005460A patent/KR940007746B1/en not_active Expired - Lifetime
- 1986-07-28 AT AT0203286A patent/AT397960B/en not_active IP Right Cessation
- 1986-07-29 ES ES8600685A patent/ES2000382A6/en not_active Expired
- 1986-07-31 CA CA000515041A patent/CA1282077C/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2200699A1 (en) * | 2002-07-12 | 2004-03-01 | Ragactives Sl | Method of separating r(-)- and s(+)-5- 2- 2-(2-ethoxyphenoxy)ethyl amino propyl-2-methoxybenzene-sulphonamide |
| WO2004006829A3 (en) * | 2002-07-12 | 2004-04-08 | Ragactives Sl | Method of separating r(-)- and s(+)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl-2-methoxybenzene-sulphonamide |
| US7105698B2 (en) | 2002-07-12 | 2006-09-12 | Ragactives, S.L. | Process for the separation of R(-)-and S(+)-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2- methoxybenzenesulfonamide |
Also Published As
| Publication number | Publication date |
|---|---|
| CA1282077C (en) | 1991-03-26 |
| JPS62114952A (en) | 1987-05-26 |
| KR940007746B1 (en) | 1994-08-24 |
| ATA203286A (en) | 1993-12-15 |
| JPH0137391B2 (en) | 1989-08-07 |
| AT397960B (en) | 1994-08-25 |
| KR870004949A (en) | 1987-06-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FD1A | Patent lapsed |
Effective date: 20060731 |