WO2008152653A2 - An improved process for the preparation of tamsulosin hydrochloride - Google Patents

An improved process for the preparation of tamsulosin hydrochloride Download PDF

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Publication number
WO2008152653A2
WO2008152653A2 PCT/IN2008/000367 IN2008000367W WO2008152653A2 WO 2008152653 A2 WO2008152653 A2 WO 2008152653A2 IN 2008000367 W IN2008000367 W IN 2008000367W WO 2008152653 A2 WO2008152653 A2 WO 2008152653A2
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Prior art keywords
formula
process according
tamsulosin
compound
methoxybenzenesulfonamide
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PCT/IN2008/000367
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French (fr)
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WO2008152653A3 (en
Inventor
Om Dutt Tyagi
Purna Chandra Ray
Konudula Babu Rao
Yogendra Kumar Chauhan
Bandlamudi Veera Narayana
Dosarala Siva Prasad Reddy
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Matrix Laboratories Ltd
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Publication of WO2008152653A3 publication Critical patent/WO2008152653A3/en

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    • 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Definitions

  • TITLE An Improved Process for the preparation of Tamsulosin Hydrochloride FIELD OF INVENTION The invention relates an improved process for preparing the (/?)-(-) 5-[2-[[2-(2- ethoxyphenoxy) ethyl] amino] propyl]-2-methoxybenzenesulfonamide of Formula I
  • Tamsulosin (R)-(-)-5 - [2- [ [2-(2-ethoxyphenoxy)ethy l]amino]propy 1] -2-methoxybenzenesulfonamide is know as Tamsulosin.
  • Tamsulosin is being marketed as its hydrochloride salt under the trade name FLOMAX. It is an ⁇ -adrenergic antagonist used preferably for treating benign prostatic hyperplasia.
  • US 4,703,063 describes two processes for the preparation of Tamsulosin, one of which involves the conversion of a hydroxyl substituted analogues of Tamsulosin, i.e., a compound having the Tamsulosin structure but contains the hydroxyl substituent at a position ⁇ to the benzenesulfonamide ring, by halogenation followed by reduction and the other process involves condensation of an appropriately substituted benzyl methyl ketone with the substituted phenoxy amine, followed by reduction of the resulting imino compound.
  • a hydroxyl substituted analogues of Tamsulosin i.e., a compound having the Tamsulosin structure but contains the hydroxyl substituent at a position ⁇ to the benzenesulfonamide ring
  • the other process involves condensation of an appropriately substituted benzyl methyl ketone with the substituted phenoxy amine, followed by reduction of the resulting imino compound.
  • CA 1,282,077 discloses a process to prepare Tamsulosin wherein (/?)-enantiomer of sulfonamide amine has been condensed with ethoxyphenoxy bromide in dimethylformamide to obtain Tamsulosin (Scheme 1) that was subsequently purified by crystallization before converting into hydrochloride salt
  • Tamsulosin hydrochloride is obtained in low yield, and therefore this process is not suitable for commercial production.
  • WO 2002/068383 Al discloses a process to prepare sulfamoyl substituted phenethylamine derivatives including Tamsulosin.
  • the described process involves a coupling reaction between (/?)-(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide with an acid or a corresponding acid chloride or mixed anhydride to produce Tamsulosin amide and thereafter reduction of the obtained compound to give Tamsulosin.
  • the coupling reaction presents the disadvantage that the acid or acid chloride or anhydride should be provided in a high purity in order to obtain a good yield in the coupling reaction and it is known in the art that purification of such products is not always easy.
  • WO 2004/022532 Al discloses a process to prepare Tamsulosin (Scheme II) wherein protected amine is used during condensation with ethoxy phenoxy derivative to obtain protected Tamsulosin. In this process, an additional step of removing the protecting group to obtain Tamsulosin in involved.
  • Tamsulosin EP 0 380 144 Bl describes a process for preparing Tamsulosin in stereospecific form, by reaction of a benzenesulfonamide amine with predetermined stereospecificity, with 2-(2- ethoxyphenoxy)ethyl halide, specifically the bromide.
  • Tamsulosin base has been purified with column chromatography.
  • WO 2004/016582 discloses a process to prepare Tamsulosin hydrochloride (Scheme III). This process involves two additional steps, first the protection of amine group before condensing with ethoxyphenoxy halide and thereafter the deprotection to obtain Tamsulosin.
  • the objective of the present invention is to provide an improved process for preparing highly pure Tamsulosin hydrochloride in high yield.
  • Yet another objective of the present invention is to provide a simple, industrially advantageous process to manufacture Tamsulosin hydrochloride.
  • Z represents a leaving group such as 0-SO 2 CH 3 , -OSO 2 C 6 H 4 CH 3 , -F, -Br, -Cl, or -I, c) extracting the reaction mass with aliphatic hydrocarbon solvents and chlorinated and d) recrystallizing the obtained reaction mass to obtain compound of Formula I
  • the present process provides an improved method for preparing Tamsulosin and in particular, optically pure (/?)-Tamsulosin.
  • the (/?)-(-)-5-(2-aminopropyl)-2- methoxybenzenesulfonamide hydrochloride of Formula II is neutralized by using liquid ammonia to yield compound of Formula III.
  • inorganic salts like sodium carbonate, potassium carbonate, sodium hydroxide or potassium hydroxide are used which generate lot of solid waste.
  • the inventors have utilized liquid ammonia as neutralizing agent.
  • the compound of Formula III is finally recrystallized from hot water.
  • the compound of Formula III is condensed with the compound of Formula IV in an alcoholic solvent.
  • the reaction mass was heated to reflux temperature and maintained for 48 hrs.
  • methanol was distilled off and aliphatic hydrocarbons were added and heated to 50 0 C for 30 minutes.
  • the aliphatic hydrocarbons employed for extraction are selected from hexanes, heptanes, cyclohexanes more preferably n-hexane.
  • the unreacted compound of Formula IV gets carried into the hexane layer which can be recovered and reused again. Initially the compound at this stage is having a purity of 30 %.
  • the compound of Formula I at this stage has a purity of 50-55%.
  • the slurry is filtered off and the obtained cake is extracted in chlorinated solvents selected from chloroform, dichloromethane, carbon tetrachloride etc.
  • the preferred choice of solvent is dichloromethane.
  • dichloromethane the unreacted (/?)-5-(2-amino- l-propyl)-2-methoxy benzenesulfonamide is recovered. Further, traces of the amine compound was removed by washing the dichloromethane layer with 20% aqueous potassium carbonate solution, followed by water washings to get crude base.
  • the obtained crude base of compound of Formula I additionally contains large amounts of overalkylated compound which were further eliminated by recrystallisation the crude reaction mass from aromatic hydrocarbon solvents selected from toluene, xylene etc, more preferably toluene.
  • the Tamsulosin base obtained contains less than 1 % of overalkylated product i.e 5-(/?)-2 ⁇ Bis-[2-(2-ethoxy- phenoxy)-ethyl]-amino ⁇ -propyl)-2-methoxy-benzenesulfonarnide and the compounds of Formula II and III are less than 0.5 %.
  • the major advantage realized in the present process of invention is the use of various solvents for purification of the crude compound of Formula I. Normally in the prior-art process this condensation leads to generation of many impurities and by-products which are difficult to remove. Hence, column chromatography is employed to remove these impurities/byproducts so as to make a purer product. Instead, a combination of solvents have been employed in the present invention so as to remove these impurities in various stages thereby avoiding column chromatography altogether.
  • the Tamsulosin base is further converted to hydrochloride in ethanol with ethanolic HCl to give pure Tamsulosin hydrochloride having less than 0.1 % of all individual impurities and less than 0.2 of total impurities.
  • Tamsulosin base (15 g, 0.036 moles) was dissolved in 225 ml of ethanol at 75-78 0 C.
  • the reaction mass was cooled to 65 0 C and charcolized.
  • the reaction mass was filtered.
  • the reaction mass cooled to 2O 0 C and pH of the reaction mass was adjusted to 2.0 with 10% ethanolic HCl.
  • the reaction mass was maintained at 25-3O 0 C for 3.0 hours and subsequently heated to reflux for 30 minutes. Cool the reaction mass to 40-45 0 C and filtered and washed the cake with 20 ml ethanol. Dry the material under vacuum at 40-50 0 C. Dry Weight : 16.O g HPLC Purity : 99.9%

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention relates an improved process for preparing the (R)-(-)5-[2-[[2-(2-ethoxyphenoxyethyl]amino]propyl]-2-methoxybenzenesulfonamide of Formula (I): and its pharmaceutically acceptable salts.

Description

TITLE: An Improved Process for the preparation of Tamsulosin Hydrochloride FIELD OF INVENTION The invention relates an improved process for preparing the (/?)-(-) 5-[2-[[2-(2- ethoxyphenoxy) ethyl] amino] propyl]-2-methoxybenzenesulfonamide of Formula I
Formula I
Figure imgf000002_0001
and its pharmaceutically acceptable salts BACKGROUND OF THE INVENTION
(R)-(-)-5 - [2- [ [2-(2-ethoxyphenoxy)ethy l]amino]propy 1] -2-methoxybenzenesulfonamide is know as Tamsulosin. Presently Tamsulosin is being marketed as its hydrochloride salt under the trade name FLOMAX. It is an α-adrenergic antagonist used preferably for treating benign prostatic hyperplasia.
US 4,703,063 describes two processes for the preparation of Tamsulosin, one of which involves the conversion of a hydroxyl substituted analogues of Tamsulosin, i.e., a compound having the Tamsulosin structure but contains the hydroxyl substituent at a position α to the benzenesulfonamide ring, by halogenation followed by reduction and the other process involves condensation of an appropriately substituted benzyl methyl ketone with the substituted phenoxy amine, followed by reduction of the resulting imino compound.
The above described processes are non-stereospecific and the final product requires an additional step of resolution of enantiomers to specifically obtain (/?)-enantiomer Tamsulosin.
CA 1,282,077 discloses a process to prepare Tamsulosin wherein (/?)-enantiomer of sulfonamide amine has been condensed with ethoxyphenoxy bromide in dimethylformamide to obtain Tamsulosin (Scheme 1) that was subsequently purified by crystallization before converting into hydrochloride salt
2-(2-ethoxyphenoxy)ethyl bromide
Figure imgf000003_0001
Tamsulosin Hydrochloride
Scheme I
As per the above described process, Tamsulosin hydrochloride is obtained in low yield, and therefore this process is not suitable for commercial production.
WO 2002/068383 Al discloses a process to prepare sulfamoyl substituted phenethylamine derivatives including Tamsulosin. The described process involves a coupling reaction between (/?)-(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide with an acid or a corresponding acid chloride or mixed anhydride to produce Tamsulosin amide and thereafter reduction of the obtained compound to give Tamsulosin. The coupling reaction presents the disadvantage that the acid or acid chloride or anhydride should be provided in a high purity in order to obtain a good yield in the coupling reaction and it is known in the art that purification of such products is not always easy. WO 2004/022532 Al discloses a process to prepare Tamsulosin (Scheme II) wherein protected amine is used during condensation with ethoxy phenoxy derivative to obtain protected Tamsulosin. In this process, an additional step of removing the protecting group to obtain Tamsulosin in involved.
Xylene
2-(2-ethoxyphenoxy)ethyI methanesulfonate Magnesium oxide
Figure imgf000004_0001
Figure imgf000004_0002
BENZYL TAMSULOSIN
Figure imgf000004_0003
TAMSULOSIN
SCHEME-II
The process involves the use of a protected amine derivative, which needs to be deprotected after the formation of Tamsulosin EP 0 380 144 Bl describes a process for preparing Tamsulosin in stereospecific form, by reaction of a benzenesulfonamide amine with predetermined stereospecificity, with 2-(2- ethoxyphenoxy)ethyl halide, specifically the bromide. In this process Tamsulosin base has been purified with column chromatography.
WO 2004/016582 discloses a process to prepare Tamsulosin hydrochloride (Scheme III). This process involves two additional steps, first the protection of amine group before condensing with ethoxyphenoxy halide and thereafter the deprotection to obtain Tamsulosin.
Figure imgf000005_0001
TAMSULOSIN
SCHEME-III
This process involves the use of a protected amine derivative, which needs to be deprotected after the formation of Tamsulosin OBJECTIVE OF THE INVENTION
The objective of the present invention is to provide an improved process for preparing highly pure Tamsulosin hydrochloride in high yield.
Yet another objective of the present invention is to provide a simple, industrially advantageous process to manufacture Tamsulosin hydrochloride.
SUMMARY OF THE INVENTION
An improved process for the preparation (/?)-5-(2-(2-ethoxyphenoxy)ethylamino)-l- propyl)-2-methoxybenzenesulfonamide hydrochloride of Formula I,
Formula I
Figure imgf000006_0001
and its pharmaceutically acceptable salts
which comprises : a) neutralizing the (/?)-(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide hydrochloride of Formula II,
.HCl Formula II
Figure imgf000006_0002
with a base to give (/?)-(-)-5-(2-arninopropyl)-2-methoxybenzenesulfonamide of Formula HI,
NHc Formula III
Figure imgf000006_0003
b) reacting the (/?)-(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide of Formula III with a substituted phenoxy compound of Formula IV.
Formula IV
Figure imgf000007_0001
wherein Z represents a leaving group such as 0-SO2CH3, -OSO2C6H4CH3, -F, -Br, -Cl, or -I, c) extracting the reaction mass with aliphatic hydrocarbon solvents and chlorinated and d) recrystallizing the obtained reaction mass to obtain compound of Formula I
DETAILED DESCRIPTION OF THE INVENTION
The present process provides an improved method for preparing Tamsulosin and in particular, optically pure (/?)-Tamsulosin.
In the first embodiment of the invention the (/?)-(-)-5-(2-aminopropyl)-2- methoxybenzenesulfonamide hydrochloride of Formula II is neutralized by using liquid ammonia to yield compound of Formula III. Normally in all the prior-art process, inorganic salts like sodium carbonate, potassium carbonate, sodium hydroxide or potassium hydroxide are used which generate lot of solid waste. In order to reduce the solid effluent, the inventors have utilized liquid ammonia as neutralizing agent. The compound of Formula III is finally recrystallized from hot water.
The compound of Formula III is condensed with the compound of Formula IV in an alcoholic solvent. The reaction mass was heated to reflux temperature and maintained for 48 hrs. After completion of the reaction, methanol was distilled off and aliphatic hydrocarbons were added and heated to 50 0C for 30 minutes. The aliphatic hydrocarbons employed for extraction are selected from hexanes, heptanes, cyclohexanes more preferably n-hexane. During this n-hexane reflux, the unreacted compound of Formula IV gets carried into the hexane layer which can be recovered and reused again. Initially the compound at this stage is having a purity of 30 %. After the hexane washing, the compound of Formula I at this stage has a purity of 50-55%. The slurry is filtered off and the obtained cake is extracted in chlorinated solvents selected from chloroform, dichloromethane, carbon tetrachloride etc. The preferred choice of solvent is dichloromethane. During this dichloromethane extraction, the unreacted (/?)-5-(2-amino- l-propyl)-2-methoxy benzenesulfonamide is recovered. Further, traces of the amine compound was removed by washing the dichloromethane layer with 20% aqueous potassium carbonate solution, followed by water washings to get crude base.
The obtained crude base of compound of Formula I additionally contains large amounts of overalkylated compound which were further eliminated by recrystallisation the crude reaction mass from aromatic hydrocarbon solvents selected from toluene, xylene etc, more preferably toluene. After recrystallization from toluene, the Tamsulosin base obtained contains less than 1 % of overalkylated product i.e 5-(/?)-2{Bis-[2-(2-ethoxy- phenoxy)-ethyl]-amino}-propyl)-2-methoxy-benzenesulfonarnide and the compounds of Formula II and III are less than 0.5 %.
The major advantage realized in the present process of invention is the use of various solvents for purification of the crude compound of Formula I. Normally in the prior-art process this condensation leads to generation of many impurities and by-products which are difficult to remove. Hence, column chromatography is employed to remove these impurities/byproducts so as to make a purer product. Instead, a combination of solvents have been employed in the present invention so as to remove these impurities in various stages thereby avoiding column chromatography altogether.
The Tamsulosin base is further converted to hydrochloride in ethanol with ethanolic HCl to give pure Tamsulosin hydrochloride having less than 0.1 % of all individual impurities and less than 0.2 of total impurities.
The compound of Formula II is prepared by known methods in literature. Example-1
Preparation of /?-(-)-5-(2-Aminopropyl-2-methoxybenzene sulphonamide
2i?,l/?-2-Methoxy-5-[2-(l-Methyl benzyl amino)propyl]benzene sulphonamide HCl (150 g 0.39 moles) of and 1500 ml methanol was charged with 15 g of activated carbon and maintained for 30 min at room temperature. After completion of the reaction, the reaction mass was filtered. The obtained filtrate was diluted with 1500 ml methanol and charged with
30 g of 10% Pd/C 50% wet. Debenzylation was carried out under 4-5 Kg/cm2 H2 pressure at
60-650C. The reaction was monitored by HPLC. After completion of the reaction, methanol was distilled off under vacuum at 45-5O0C. The residue was neutralized with aqueous ammonia (240 ml of 20% solution) and crystallized from hot water to give pure product.
Weight :76 g (80% yield) HPLC purity 99.8%, and chiral purity 99.8%.
ExampIe-2
Preparation of Tamsulosin base
/?-(-)-5-(2-Amino propyl-2-methoxybenzene sulphonamide (25 g 0.10 moles) of in 425 ml of methanol and 1 -(2-Bromoethoxy)-2-ethoxy benzene (37.5 g, 0.15 moles) was charged at 25- 350C. The reaction mass was heated to reflux and maintained for 48 hours. The methanol was distilled off under vacuum at below 550C. The residue was extracted with 375 ml of n-hexane twice to recover l-(2-Bromoethoxy)-2-ethoxy benzene. The residue after n-Hexane extracts is further extracted twice with methylene chloride 300 ml the undissloved is R-(-)-5-(2- Amino propyl-2-methoxybenzene sulphonamide and can be recycled. The methylene chloride layer is washed twice with 210 ml of 20% potassium carbonate solution. Wash twice with 210 ml of water, distill off methylene chloride. The crude product was recrystallized twice with 290 ml Toluene. Material was dried at 5O0C. Weight : 15 g : HPLC purity : 99% Dimer content NMT 1.0% Example -3
Preparation of Tamsulosin Hydrochloride
Tamsulosin base (15 g, 0.036 moles) was dissolved in 225 ml of ethanol at 75-780C. The reaction mass was cooled to 650C and charcolized. The reaction mass was filtered. The reaction mass cooled to 2O0C and pH of the reaction mass was adjusted to 2.0 with 10% ethanolic HCl. The reaction mass was maintained at 25-3O0C for 3.0 hours and subsequently heated to reflux for 30 minutes. Cool the reaction mass to 40-450C and filtered and washed the cake with 20 ml ethanol. Dry the material under vacuum at 40-50 0C. Dry Weight : 16.O g HPLC Purity : 99.9%

Claims

WE CLAIM :
1) An improved process for the preparation (/?)-5-(2-(2-ethoxyphenoxy)ethylamino)-l- propyl)-2-methoxybenzenesulfonamide of Formula I
Formula I
Figure imgf000011_0001
and its pharmaceutically acceptable salts which comprises : a) neutralizing the (/?)-(-)-5-(2-aminopropyl)-2-rnethoxybenzenesulfonamide hydrochloride of Formula II,
.HCl Formula II
Figure imgf000011_0002
with a base to give (/?)-(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide of Formula HI,
Formula HI
Figure imgf000011_0003
b) reacting the (i?)-(-)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide of Formula III with a substituted phenoxy compound of Formula IV,
Formula IV
Figure imgf000011_0004
wherein Z represents a leaving group such as 0-SO2CH3, -OSO2C6H4CH3, -F, -Br, -Cl, or
-I, c) extracting the reaction mass of claim Ib with aliphatic hydrocarbon solvents, chlorinated solvents, d) recrystallizing the crude reaction mass of claim Ic to give compound of Formula I
2) The process according to claim 1, wherein the base employed in step(a) is ammonia.
3) The process according to claim 1 , step (c) wherein extraction is performed by employing aliphatic hydrocarbons, chlorinated hydrocarbons.
4) The process according to claim 3, wherein the extraction is performed employing aliphatic hydrocarbons that are selected from n-hexanes, heptanes, cyclohexane
5) The process according to claim 4, wherein the solvent employed is n-hexane
6) The process according to claim l,step(c) wherein the extraction is performed employing chlorinated hydrocarbons that are selected from chloroform, carbon tetrachloride or dichloromethane
7) The process according to claim 6, wherein the chlorinated hydrocarbon employed is dichloromethane .
8) The process according to claim 1, step(d) wherein the compound of Formula I is recrystallized from aromatic hydrocarbon solvents selected from toluene, xylene more preferably toluene.
9) The process according to claim 8, wherein the hydrocarbon solvent employed is toluene.
10) The process according to claim 1, wherein the compound of Formula I is having a purity of > 99 %.
PCT/IN2008/000367 2007-06-11 2008-06-10 An improved process for the preparation of tamsulosin hydrochloride WO2008152653A2 (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102898336A (en) * 2012-10-16 2013-01-30 北京悦康科创医药科技有限公司 Preparation method of tamsulosin hydrochloride

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1282077C (en) * 1985-11-13 1991-03-26 Kunihiro Niigata Process for producing substituted-phenethylamine derivatives
WO2003035608A1 (en) * 2001-10-25 2003-05-01 Leciva, A.S. A method of the preparation of (r)-(-)-5`2-`2-(2-ethoxyphenoxy) ethylamino! propyl!-2-methoxybenzenesulphonamide (tamsulosin)
WO2004087623A2 (en) * 2003-03-07 2004-10-14 Alembic Limited An improved process for the preparation of (r) (-) tamsulosin hydrochloride
EP1734036A1 (en) * 2005-06-14 2006-12-20 Well-being Biochemical Corp. Process for preparation of tamsulosin and its derivatives

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA1282077C (en) * 1985-11-13 1991-03-26 Kunihiro Niigata Process for producing substituted-phenethylamine derivatives
WO2003035608A1 (en) * 2001-10-25 2003-05-01 Leciva, A.S. A method of the preparation of (r)-(-)-5`2-`2-(2-ethoxyphenoxy) ethylamino! propyl!-2-methoxybenzenesulphonamide (tamsulosin)
WO2004087623A2 (en) * 2003-03-07 2004-10-14 Alembic Limited An improved process for the preparation of (r) (-) tamsulosin hydrochloride
EP1734036A1 (en) * 2005-06-14 2006-12-20 Well-being Biochemical Corp. Process for preparation of tamsulosin and its derivatives

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102898336A (en) * 2012-10-16 2013-01-30 北京悦康科创医药科技有限公司 Preparation method of tamsulosin hydrochloride
CN102898336B (en) * 2012-10-16 2013-11-27 北京悦康科创医药科技有限公司 Preparation method of tamsulosin hydrochloride

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