WO2003035608A1 - A method of the preparation of (r)-(-)-5`2-`2-(2-ethoxyphenoxy) ethylamino! propyl!-2-methoxybenzenesulphonamide (tamsulosin) - Google Patents
A method of the preparation of (r)-(-)-5`2-`2-(2-ethoxyphenoxy) ethylamino! propyl!-2-methoxybenzenesulphonamide (tamsulosin) Download PDFInfo
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- WO2003035608A1 WO2003035608A1 PCT/CZ2002/000053 CZ0200053W WO03035608A1 WO 2003035608 A1 WO2003035608 A1 WO 2003035608A1 CZ 0200053 W CZ0200053 W CZ 0200053W WO 03035608 A1 WO03035608 A1 WO 03035608A1
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- WIPO (PCT)
- Prior art keywords
- reaction
- accordance
- formula
- ethanol
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- Prior art date
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- 238000000034 method Methods 0.000 title claims description 17
- DRHKJLXJIQTDTD-OAHLLOKOSA-N Tamsulosine Chemical compound CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 DRHKJLXJIQTDTD-OAHLLOKOSA-N 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 5
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 title description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 title description 2
- 229960002613 tamsulosin Drugs 0.000 title description 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 22
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 239000002585 base Substances 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 3
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 239000003880 polar aprotic solvent Substances 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- 150000003512 tertiary amines Chemical class 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 64
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 14
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- IOYHGBZPUZBUTJ-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1OCCBr IOYHGBZPUZBUTJ-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 238000001704 evaporation Methods 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 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 description 7
- 239000012074 organic phase Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- ZZIZZTHXZRDOFM-XFULWGLBSA-N tamsulosin hydrochloride Chemical compound [H+].[Cl-].CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 ZZIZZTHXZRDOFM-XFULWGLBSA-N 0.000 description 6
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- -1 2- (2-ETHOXYPHENOXY) ETHYLAMINO Chemical class 0.000 description 2
- DRHKJLXJIQTDTD-UHFFFAOYSA-N 5-(2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl)-2-methoxybenzenesulfonamide Chemical compound CCOC1=CC=CC=C1OCCNC(C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 DRHKJLXJIQTDTD-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000002035 prolonged effect Effects 0.000 description 2
- 210000002307 prostate Anatomy 0.000 description 2
- 102000005962 receptors Human genes 0.000 description 2
- 108020003175 receptors Proteins 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 210000001635 urinary tract Anatomy 0.000 description 2
- RQEUFEKYXDPUSK-SSDOTTSWSA-N (1R)-1-phenylethanamine Chemical compound C[C@@H](N)C1=CC=CC=C1 RQEUFEKYXDPUSK-SSDOTTSWSA-N 0.000 description 1
- PJPREWNCIPMGIS-UHFFFAOYSA-N 2-(sulfamoylamino)ethylbenzene Chemical class NS(=O)(=O)NCCC1=CC=CC=C1 PJPREWNCIPMGIS-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229940122878 Alpha 1 adrenoreceptor antagonist Drugs 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- 229910019020 PtO2 Inorganic materials 0.000 description 1
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical class [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 102000004305 alpha Adrenergic Receptors Human genes 0.000 description 1
- 108090000861 alpha Adrenergic Receptors Proteins 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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
- C07C303/36—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 invention relates to a method of preparing (R)-(-)-5-[2-[2-(2- ethoxyphenoxy)ethylamino]propyl]-2 ⁇ methoxybenzenesulphonamide (termed tamsulosine below) of formula I
- the compound I has been known as a selective blocker of o ⁇ c receptors, which allows its use for a treatment of urine-retention problems in connection with hyperplasic prostate without influencing blood pressure. This property distinguishes the compound I from a number of other blockers of ⁇ i receptors, which do not act selectively and, therefore, show side effects in the form of hypotension connected with various unpleasant conditions for the patient (e.g. EP 710 486).
- (R)-amine III is alkylated with bromide IV in such a way that an excess of the expensive amine is used (2 equivalents) and the reaction is performed via prolonged boiling in ethanol (16 hours).
- the reaction mixture is subjected to alkaline processing and the crude product, which contains unreacted starting amine III, is purified using column chromatography.
- the obtained base of tamsulosine I is finally converted to its hydrochloride.
- the invention relates to the preparation of (R)-(-)-5-[2-[2-(2- ethoxyphenoxy)ethylamino]propyl]-2-methoxybenzenesulphonamide, i.e. of the compound of the formula I,
- X M ⁇ rv ⁇ m, equal to from 1 to 1.1, wherein Nm and Nrv, resp., are numbers of mols of the compounds III and IN, respectively, entering the reaction.
- the reaction is carried out in the presence of an inexpensive base and in the environment of a polar aprotic solvent.
- reaction rate of the contemplated competing reaction depends first of all on the choice of the external reagent. For this purpose, it is an advantageous to opt for such a base that is dissociated more than amine III in the given reaction environment.
- solvent is also crucial for the reaction of the invention, which solvent forms, to a substantial extent, the reaction environment, which will influence velocity of the main reaction of amine DI with brominated ether IN. In the same way, it impacts other reactions that lead to undesirable products.
- solvents are dialkylamides, e.g. dimethylformamide, dimethylacetamide, ⁇ -methylpyrrolidone, or dialkylsulphoxides, such as, for example, dimethylsulphoxide, sulpholane.
- the third important factor is temperature, which can range from 60 to 140 °C.
- an especially advantageous setting is the one in which the reaction runs in dimethylformamide or dimethylsulphoxide in the presence of potassium carbonate at temperatures 60 up to 140 °C for 2 to 8 hours.
- HX hydrochloric acid
- the obtained tamsulosine hydrochloride (1.0 g; 45 % of the theoretical yield) was purified by releasing the base with 10% aqueous solution of sodium hydroxide in ethanol and repeated conversion to tamsulosine hydrochloride with ethanolic hydrogen chloride in ethanol.
- Example 6 Anhydrous diisopropylethylamine (Huenig's base; 1.85 ml; 10.8 mmol) is added to the solution of (R)-(-)-5-(2-aminopropyl)-2-methoxybenzenesulphonamide (2.45 g; 10 mmol) and 2-(2-ethoxyphenoxy)ethylbromide (2.5g; 10.2 mmol) in dimethylsulphoxide (40 ml) and the reaction mixture is stirred and heated for 4 hours under a reflux condenser at a temperature of 90 - 95°C. After cooling down, water is added (50 ml) and the mixture is extracted with ethyl acetate (3 x 50 ml).
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ20013848A CZ291802B6 (cs) | 2001-10-25 | 2001-10-25 | Způsob výroby (R)-(-)-5-[2-[2-(2-ethoxyfenoxy)ethylamino]propyl]-2-methoxybenzensulfonamidu |
| CZPV2001-3848 | 2001-10-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2003035608A1 true WO2003035608A1 (en) | 2003-05-01 |
Family
ID=5473599
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/CZ2002/000053 WO2003035608A1 (en) | 2001-10-25 | 2002-10-03 | A method of the preparation of (r)-(-)-5`2-`2-(2-ethoxyphenoxy) ethylamino! propyl!-2-methoxybenzenesulphonamide (tamsulosin) |
Country Status (2)
| Country | Link |
|---|---|
| CZ (1) | CZ291802B6 (cs) |
| WO (1) | WO2003035608A1 (cs) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2864079A1 (fr) * | 2003-12-17 | 2005-06-24 | Prod Chim Auxiliaires Et De Sy | Nouveaux intermediaires de syntheses de la (r)-tamsulosine et de ses sels pharmaceutiquement acceptables et procede pour leur preparation |
| WO2005063702A1 (en) * | 2003-12-29 | 2005-07-14 | Lek Pharmaceuticals D.D. | Preparation of r-5-(2-(2-ethoxyphenoxyetylamino)propyl)-2- methoxybenzenesulphonamide hydrochloride of high chemical |
| WO2005063701A1 (en) * | 2003-12-29 | 2005-07-14 | Lek Pharmaceuticals D.D. | Synthesis of optically pure (r)-5-(2-aminopropyl)-2-methoxybenzenesulphonamide |
| WO2006061549A1 (en) * | 2004-12-06 | 2006-06-15 | Hovione Inter Ltd. | Process for the preparation of tamsulosin and intermediates thereof |
| WO2006019358A3 (en) * | 2004-08-16 | 2006-12-07 | Scinopharm Singapore Pte Ltd | Process for preparing tamsulosin |
| WO2006117662A3 (en) * | 2005-05-03 | 2007-01-04 | Ranbaxy Lab Ltd | Polymorphic forms of (r)-(-)-tamsulosin |
| WO2006134212A3 (en) * | 2005-06-15 | 2007-02-22 | Fermion Oy | Preparation of tamsulosin hydrochloride from tamsulosi |
| US7238839B2 (en) | 2004-10-07 | 2007-07-03 | Divi's Laboratories Limited | Process for the resolution of racemic (R,S) -5-(2-(2-(2- ethoxyphenoxy) ethylamino)Propyl)-2-methoxybenzene sulfonamide (tamsulosin), its novel R and S isomers and their salts and processes for their preparation |
| WO2007119110A3 (en) * | 2005-10-28 | 2008-02-28 | Medichem Sa | Process for the preparation of tamsulosin and related compounds |
| WO2008152653A3 (en) * | 2007-06-11 | 2010-04-29 | Matrix Laboratories Ltd | An improved process for the preparation of tamsulosin hydrochloride |
| EP2255793A1 (en) | 2009-05-28 | 2010-12-01 | Krka Tovarna Zdravil, D.D., Novo Mesto | Pharmaceutical composition comprising tamsulosin |
| US8273918B2 (en) * | 2005-09-12 | 2012-09-25 | Avrobindo Pharma Ltd. | Process for preparing tamsulosin hydrochloride |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT397960B (de) * | 1985-11-13 | 1994-08-25 | Yamanouchi Pharma Co Ltd | Verfahren zur herstellung des neuen r-(-)-5-(2-((2-(o-äthoxyphenoxy)-äthyl)-amino)- propyl)-2-methoxybenzolsulfonamids |
| EP0710486A1 (en) * | 1993-07-14 | 1996-05-08 | Yamanouchi Pharmaceutical Co. Ltd. | Remedy for urination disorder accompanying prostatic hypertrophy |
-
2001
- 2001-10-25 CZ CZ20013848A patent/CZ291802B6/cs not_active IP Right Cessation
-
2002
- 2002-10-03 WO PCT/CZ2002/000053 patent/WO2003035608A1/en not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT397960B (de) * | 1985-11-13 | 1994-08-25 | Yamanouchi Pharma Co Ltd | Verfahren zur herstellung des neuen r-(-)-5-(2-((2-(o-äthoxyphenoxy)-äthyl)-amino)- propyl)-2-methoxybenzolsulfonamids |
| EP0710486A1 (en) * | 1993-07-14 | 1996-05-08 | Yamanouchi Pharmaceutical Co. Ltd. | Remedy for urination disorder accompanying prostatic hypertrophy |
Cited By (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005058810A1 (en) * | 2003-12-17 | 2005-06-30 | Produits Chimiques Auxiliaires Et De Synthese | Novel intermediates for the synthesis of (r)-tamsulosin and of its pharmaceutically acceptable salts and process for their preparation |
| FR2864079A1 (fr) * | 2003-12-17 | 2005-06-24 | Prod Chim Auxiliaires Et De Sy | Nouveaux intermediaires de syntheses de la (r)-tamsulosine et de ses sels pharmaceutiquement acceptables et procede pour leur preparation |
| US7619116B2 (en) | 2003-12-17 | 2009-11-17 | Products Chimiques Auxiliaires Et de Synthese | Intermediates for the synthesis of (R)-tamsulosin and of its pharmaceutically acceptable salts and process for their preparation |
| US7538246B2 (en) | 2003-12-29 | 2009-05-26 | Lek Pharmaceuticals D.D. | Synthesis of optically pure(r)-5-(2-amynopropyl)-2-methoxybenzenesulphonamide |
| WO2005063702A1 (en) * | 2003-12-29 | 2005-07-14 | Lek Pharmaceuticals D.D. | Preparation of r-5-(2-(2-ethoxyphenoxyetylamino)propyl)-2- methoxybenzenesulphonamide hydrochloride of high chemical |
| WO2005063701A1 (en) * | 2003-12-29 | 2005-07-14 | Lek Pharmaceuticals D.D. | Synthesis of optically pure (r)-5-(2-aminopropyl)-2-methoxybenzenesulphonamide |
| AU2004309315B8 (en) * | 2003-12-29 | 2011-12-15 | Lek Pharmaceuticals D.D. | Preparation of R-5-(2-(2-(2-ethoxyphenoxy)ethylamino)propyl)-2-methoxybenzenesulphonamide hydrochloride of high chemical purity |
| AU2004309315B2 (en) * | 2003-12-29 | 2011-10-20 | Lek Pharmaceuticals D.D. | Preparation of R-5-(2-(2-(2-ethoxyphenoxy)ethylamino)propyl)-2-methoxybenzenesulphonamide hydrochloride of high chemical purity |
| AU2004309314B2 (en) * | 2003-12-29 | 2011-09-01 | Lek Pharmaceuticals D.D. | Synthesis of optically pure (R)-5-(2-aminopropyl)-2-methoxybenzenesulphonamide |
| RU2419605C2 (ru) * | 2003-12-29 | 2011-05-27 | Лек Фармасьютиклз Д.Д. | Синтез оптически чистого (r)-5-(2-аминопропил)-2-метоксибензолсульфонамида |
| JP2007517797A (ja) * | 2003-12-29 | 2007-07-05 | レツク・フアーマシユーテイカルズ・デー・デー | 高化学的ｒ−５−（２−（２−エトキシフェノキシエチルアミノ）プロピル）−２−メトキシベンゼンスルホンアミド塩酸塩の調製 |
| CN1902165B (zh) * | 2003-12-29 | 2010-06-16 | 力奇制药公司 | 光学纯(r)-5-(2-氨基丙基)-2-甲氧基苯磺酰胺的合成 |
| WO2006019358A3 (en) * | 2004-08-16 | 2006-12-07 | Scinopharm Singapore Pte Ltd | Process for preparing tamsulosin |
| US7332621B2 (en) | 2004-08-16 | 2008-02-19 | Scinopharm Taiwan Ktd. | Process for preparing Tamsulosin |
| US7238839B2 (en) | 2004-10-07 | 2007-07-03 | Divi's Laboratories Limited | Process for the resolution of racemic (R,S) -5-(2-(2-(2- ethoxyphenoxy) ethylamino)Propyl)-2-methoxybenzene sulfonamide (tamsulosin), its novel R and S isomers and their salts and processes for their preparation |
| US8017803B2 (en) | 2004-12-06 | 2011-09-13 | Hovione Inter Ltd. | Process for the preparation of tamsulosin and intermediates thereof |
| WO2006061549A1 (en) * | 2004-12-06 | 2006-06-15 | Hovione Inter Ltd. | Process for the preparation of tamsulosin and intermediates thereof |
| WO2006117662A3 (en) * | 2005-05-03 | 2007-01-04 | Ranbaxy Lab Ltd | Polymorphic forms of (r)-(-)-tamsulosin |
| WO2006134212A3 (en) * | 2005-06-15 | 2007-02-22 | Fermion Oy | Preparation of tamsulosin hydrochloride from tamsulosi |
| US8273918B2 (en) * | 2005-09-12 | 2012-09-25 | Avrobindo Pharma Ltd. | Process for preparing tamsulosin hydrochloride |
| WO2007119110A3 (en) * | 2005-10-28 | 2008-02-28 | Medichem Sa | Process for the preparation of tamsulosin and related compounds |
| WO2008152653A3 (en) * | 2007-06-11 | 2010-04-29 | Matrix Laboratories Ltd | An improved process for the preparation of tamsulosin hydrochloride |
| EP2255793A1 (en) | 2009-05-28 | 2010-12-01 | Krka Tovarna Zdravil, D.D., Novo Mesto | Pharmaceutical composition comprising tamsulosin |
Also Published As
| Publication number | Publication date |
|---|---|
| CZ20013848A3 (cs) | 2003-05-14 |
| CZ291802B6 (cs) | 2003-05-14 |
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