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US20060036113A1 - Process for preparing tamsulosin - Google Patents

Process for preparing tamsulosin Download PDF

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Publication number
US20060036113A1
US20060036113A1 US11/201,878 US20187805A US2006036113A1 US 20060036113 A1 US20060036113 A1 US 20060036113A1 US 20187805 A US20187805 A US 20187805A US 2006036113 A1 US2006036113 A1 US 2006036113A1
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US
United States
Prior art keywords
process according
mixtures
group
solvent
conducted
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.)
Abandoned
Application number
US11/201,878
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English (en)
Inventor
Meihua Xie
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Scinopharm Taiwan Ltd
Original Assignee
Scinopharm Taiwan Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Scinopharm Taiwan Ltd filed Critical Scinopharm Taiwan Ltd
Assigned to SCINOPHARM TAIWAN LTD. reassignment SCINOPHARM TAIWAN LTD. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: XIE, MEIHUA
Publication of US20060036113A1 publication Critical patent/US20060036113A1/en
Assigned to SCINOPHARM TAIWAN LTD. reassignment SCINOPHARM TAIWAN LTD. CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE'S ADDRESS PREVIOUSLY RECORDED ON AUGUST 11, 2005 ON REEL 016866 FRAME 0129. Assignors: XIE, MEIHUA
Priority to US11/644,328 priority Critical patent/US7332621B2/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
    • C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/36—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids
    • C07C303/40—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of amides of sulfonic acids by reactions not involving the formation of sulfonamide groups

Definitions

  • the present invention relates to a process for preparing Tamsulosin, an anti-benign prostatic hyperplasia drug.
  • Tamsulosin is (R)-( ⁇ )-5-[2-[[2-(2-ethoxyphenoxy)ethyl]amino]propyl]-2-methoxybenzenesulfonamide hydrochloride, with the following structural formula (1):
  • Tamsulosin is a selective antagonist of ⁇ 1c -receptor, which was clinically used for treating hypertension initially, and now is mainly used for treating benign prostatic hyperplasia. Tamsulosin was developed by Yamanouchi Pharmaceutical Co., Ltd. of Japan and firstly commercialized in Japan in 1996. Yamanouchi Pharmaceutical Co. Ltd. owns a patent, EP 0 034 432 (published on Aug. 26, 1981), for Tamsulosin.
  • EP 0 034 432 to Imai et al. discloses a synthetic route of Tamsulosin as follows:
  • Tamsulosin is prepared by condensation of 2-(2-ethoxyphenoxy)-acetaldehyde with R-( ⁇ )-5(2-aminopropyl)-2-methoxybenzenesulfonamide and followed by reduction.
  • the use of 5% Pd/C can obtain a reduction yield of 32.8%
  • the use of NaBH 3 CN can obtain a reduction yield of 57.2%.
  • the synthetic route is as follows:
  • Tamsulosin is prepared by condensation of 2-methoxy-5-(2-oxopropyl)-5 benzenesulfonamide with 2-(2-ethoxyphenoxy)-1-ethanamine and followed by reduction to afford DL-Tamsulosin, which is then salified with (+)camphor-10-sulphonic acid, resolved into individual optical isomers, and then recrystallized four times to produce Tamsulosin, with a yield of 8.9%.
  • the synthetic route is as follows:
  • the present invention relates to a novel process for preparing Tamsulosin, which includes reacting o-ethoxyphenoxyethanol with sulfonyl chloride to produce a sulfonate, and then condensating the resulted sulfonate with an optically active amine, (R)-( ⁇ )-5-(2-aminopropyl)-2-methoxybenzenesulfonamide to produce Tamsulosin.
  • the synthetic route is as follows:
  • the present invention relates to a novel process for preparing Tamsulosin, which includes reacting o-ethoxyphenoxyethanol with sulfonyl chloride to produce a sulfonate, and then condensating the resulted sulfonate with an optically active amine, (R)-( ⁇ )-5-(2-aminopropyl)-2-methoxybenzenesulfonamide to produce Tamsulosin.
  • the synthetic route is as follows:
  • the process of the present invention includes the following two steps: (i) reacting o-ethoxyphenoxyethanol (compound (2)) with sulfonyl chloride of Formula RSO 2 Cl to produce o-ethoxyphenoxyethanol sulfonate (compound (3)), wherein R is (C 1 -C 6 )alkyl, such as methyl and ethyl, or phenyl substituted by halogen, nitro and/or (C 1 -C 6 )alkyl (such as methyl), preferably substituted at the ortho, para, or meta position; and (ii) reacting the compound (3) with (R)-( ⁇ )-5-(2-aminopropyl)-2-methoxybenzenesulfonamide (compound (4)) with a suitable organic amine and/or inorganic base as an acid scavenger at a temperature of about 40 to 100° C., in the presence of a catalyst and a suitable solvent, to prepare Tamsulosin.
  • R
  • the compound (2) is dissolved into an organic solvent (the suitable solvent is selected from the group consisting of chloromethane (preferably dichloromethane and/or trichloromethane), chloroethane (preferably dichloroethane), benzene, substituted benzene (preferably toluene), pyridine, other similar organic solvents and mixtures thereof, stirred until they are fully dissolved, and cooled to about ⁇ 10 to 10° C., preferably about ⁇ 5 to 5° C., more preferably about ⁇ 5 to 0° C.
  • chloromethane preferably dichloromethane and/or trichloromethane
  • chloroethane preferably dichloroethane
  • benzene substituted benzene
  • pyridine other similar organic solvents and mixtures thereof
  • sulfonyl chloride of Formula RSO 2 Cl (wherein R is (C 1 -C 6 )alkyl, such as methyl and ethyl, or phenyl substituted by halogen, nitro and/or (C 1 -C 6 )alkyl (such as methyl), preferably substituted at the ortho, para, and meta position) is added dropwise into the mixture.
  • R is (C 1 -C 6 )alkyl, such as methyl and ethyl, or phenyl substituted by halogen, nitro and/or (C 1 -C 6 )alkyl (such as methyl), preferably substituted at the ortho, para, and meta position
  • R is (C 1 -C 6 )alkyl, such as methyl and ethyl, or phenyl substituted by halogen, nitro and/or (C 1 -C 6 )alkyl (such as methyl), preferably substituted at the ortho, para, and meta position)
  • the compound (3), an organic amine and/or inorganic base as an acid scavenger, a catalyst and a suitable solvent are added into a reaction flask and heated to about 40-50° C., and then the compound (4) is added in portions;
  • the organic amine as an acid scavenger is selected from the group consisting of an organic tertiary amine, pyridine and mixtures thereof, preferably the group consisting of triethylamine, pyridine and mixtures thereof;
  • the inorganic base as an acid scavenger is selected from the group consisting of KOH, NaOH, K 2 CO 3 , NaHCO 3 , the like and mixtures thereof;
  • the catalyst is selected from the group consisting of monovalent inorganic iodides, preferably the group consisting of potassium iodide (KI), sodium iodide (NaI), copper iodide (CuI) and mixtures thereof;
  • the proper solvent is an aprotic organic solvent, preferably selected
  • the reaction mixture is heated at a temperature of about 50-100° C., preferably about 50-80° C., more preferably about 55-65° C., until the compound (3) disappears. Then, the mixture is cooled to room temperature, added with water, extracted with ethyl acetate or the like, distilled off the solvent under reduced pressure, and added with an organic solvent containing HCl (preferably selected from the group consisting of ethyl acetate-HCl, CH 3 OH—HCl, EtOH—HCl, (CH 3 ) 2 CHOH—HCl and mixtures thereof) to isolate white solids, which are then recrystallized with an aqueous methanol, various aqueous, alcohols, acetone, or dissolvants of above in mixure with ethyl acetate, methyl tert-butyl ether, benzene and/or toluene to produce Tamsulosin, with a yield of 55-70%.
  • HCl preferably selected from the
  • the ethyl acetate extract solutions are combined, rinsed twice with 100 ml water, dried with anhydrous magnesium sulfate, and distilled off ethyl acetate under reduced pressure. After that, the residue is dissolved in ethanol and filtered while it is still warm. The filtrate is cooled to room temperature, and EtOH—HCl is added gradually until the filtrate has a pH of 2. White solids are isolated. Thereafter, the solids are recrystallized with aqueous ethanol to isolate white crystals, which are then filtered, washed with ethanol, and dried to obtain 20.4 g title compound. Yield: 56.9%.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
US11/201,878 2004-08-16 2005-08-11 Process for preparing tamsulosin Abandoned US20060036113A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US11/644,328 US7332621B2 (en) 2004-08-16 2006-12-22 Process for preparing Tamsulosin

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CN200410058397.6 2004-08-16
CNB2004100583976A CN100545148C (zh) 2004-08-16 2004-08-16 一种抗良性前列腺肥大药物坦索罗辛之合成方法

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US11/644,328 Division US7332621B2 (en) 2004-08-16 2006-12-22 Process for preparing Tamsulosin

Publications (1)

Publication Number Publication Date
US20060036113A1 true US20060036113A1 (en) 2006-02-16

Family

ID=35800874

Family Applications (2)

Application Number Title Priority Date Filing Date
US11/201,878 Abandoned US20060036113A1 (en) 2004-08-16 2005-08-11 Process for preparing tamsulosin
US11/644,328 Expired - Fee Related US7332621B2 (en) 2004-08-16 2006-12-22 Process for preparing Tamsulosin

Family Applications After (1)

Application Number Title Priority Date Filing Date
US11/644,328 Expired - Fee Related US7332621B2 (en) 2004-08-16 2006-12-22 Process for preparing Tamsulosin

Country Status (4)

Country Link
US (2) US20060036113A1 (fr)
EP (1) EP1786764B1 (fr)
CN (1) CN100545148C (fr)
WO (1) WO2006019358A2 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070015939A1 (en) * 2005-07-13 2007-01-18 Jih Ru H Process for preparation of tamsulosin and its aralkylamine derivatives
US20100267987A1 (en) * 2005-09-12 2010-10-21 Aur Obindo Pharma Ltd Process for Preparing Tamsulosin Hydrochloride

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN100569745C (zh) * 2005-05-27 2009-12-16 国际威林生化科技股份有限公司 制备坦舒乐欣的方法
CN102898336B (zh) * 2012-10-16 2013-11-27 北京悦康科创医药科技有限公司 一种盐酸坦索罗辛的制备方法
KR101525493B1 (ko) * 2013-01-02 2015-06-03 보령제약 주식회사 고순도 탐술로신 또는 이의 염 제조방법

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4731478A (en) * 1980-02-08 1988-03-15 Yamanouchi Pharmaceutical Co., Ltd. Sulfamoyl-substituted phenethylamine derivatives, their preparation, and pharmaceutical compositions, containing them

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2825736A (en) * 1953-01-30 1958-03-04 Merck & Co Inc Sulfonic acid esters of ethanolamines
JPS62114952A (ja) 1985-11-13 1987-05-26 Yamanouchi Pharmaceut Co Ltd 置換フエネチルアミン誘導体の製造法
JPH066565B2 (ja) * 1986-07-21 1994-01-26 山之内製薬株式会社 光学活性なベンゼンスルホンアミド誘導体の製造法
JP3662761B2 (ja) * 1999-02-10 2005-06-22 アステラス製薬株式会社 フェノキシアルキルハライド誘導体の新規製造法
CZ291802B6 (cs) * 2001-10-25 2003-05-14 Léčiva, A.S. Způsob výroby (R)-(-)-5-[2-[2-(2-ethoxyfenoxy)ethylamino]propyl]-2-methoxybenzensulfonamidu
US6835853B2 (en) * 2001-10-31 2004-12-28 Synthon Bv Process for resolution of tamsulosin and compounds, compositions, and processes associated therewith
WO2004016582A1 (fr) * 2002-08-14 2004-02-26 Natco Pharma Limited Procede ameliore de preparation de chlorhydrate de tamsulosine
HU225505B1 (en) * 2002-09-09 2007-01-29 Richter Gedeon Vegyeszet Process for the preparation of r-(-)-tamsulosin hydrochloride and novel intermediates
WO2004087623A2 (fr) * 2003-03-07 2004-10-14 Alembic Limited Procede ameliore de preparation de (r) (-) tamsulosine chlorhydrate

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4731478A (en) * 1980-02-08 1988-03-15 Yamanouchi Pharmaceutical Co., Ltd. Sulfamoyl-substituted phenethylamine derivatives, their preparation, and pharmaceutical compositions, containing them

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070015939A1 (en) * 2005-07-13 2007-01-18 Jih Ru H Process for preparation of tamsulosin and its aralkylamine derivatives
US7282606B2 (en) * 2005-07-13 2007-10-16 Well-Being Biochemical Corp. Process for preparation of tamsulosin and its aralkylamine derivatives
US20100267987A1 (en) * 2005-09-12 2010-10-21 Aur Obindo Pharma Ltd Process for Preparing Tamsulosin Hydrochloride
US8273918B2 (en) 2005-09-12 2012-09-25 Avrobindo Pharma Ltd. Process for preparing tamsulosin hydrochloride

Also Published As

Publication number Publication date
US7332621B2 (en) 2008-02-19
WO2006019358A3 (fr) 2006-12-07
EP1786764B1 (fr) 2017-03-15
EP1786764A2 (fr) 2007-05-23
US20070142669A1 (en) 2007-06-21
CN1736984A (zh) 2006-02-22
CN100545148C (zh) 2009-09-30
EP1786764A4 (fr) 2009-11-11
WO2006019358A2 (fr) 2006-02-23

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Legal Events

Date Code Title Description
AS Assignment

Owner name: SCINOPHARM TAIWAN LTD., TAIWAN

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST;ASSIGNOR:XIE, MEIHUA;REEL/FRAME:016866/0129

Effective date: 20050623

AS Assignment

Owner name: SCINOPHARM TAIWAN LTD., TAIWAN

Free format text: CORRECTIVE ASSIGNMENT TO CORRECT THE ASSIGNEE'S ADDRESS PREVIOUSLY RECORDED ON AUGUST 11, 2005 ON REEL 016866 FRAME 0129;ASSIGNOR:XIE, MEIHUA;REEL/FRAME:017852/0026

Effective date: 20050623

STCB Information on status: application discontinuation

Free format text: ABANDONED -- FAILURE TO RESPOND TO AN OFFICE ACTION