ATE427930T1 - Verfahren zur herstellung von tamsulosin und zwischenprodukten davon - Google Patents
Verfahren zur herstellung von tamsulosin und zwischenprodukten davonInfo
- Publication number
- ATE427930T1 ATE427930T1 AT05701921T AT05701921T ATE427930T1 AT E427930 T1 ATE427930 T1 AT E427930T1 AT 05701921 T AT05701921 T AT 05701921T AT 05701921 T AT05701921 T AT 05701921T AT E427930 T1 ATE427930 T1 AT E427930T1
- Authority
- AT
- Austria
- Prior art keywords
- formula
- compound
- methoxy
- propyl
- benzenesulfonic acid
- Prior art date
Links
- 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 abstract 2
- 239000013067 intermediate product Substances 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 7
- 150000003839 salts Chemical class 0.000 abstract 4
- ZIDMEUOHWXPUFW-SSDOTTSWSA-N 5-[(2r)-2-aminopropyl]-2-methoxybenzenesulfonic acid Chemical compound COC1=CC=C(C[C@@H](C)N)C=C1S(O)(=O)=O ZIDMEUOHWXPUFW-SSDOTTSWSA-N 0.000 abstract 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 229940092714 benzenesulfonic acid Drugs 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 abstract 1
- -1 5-{(2R)-2-[2-(2-ethoxy-phenoxy)-ethylamino]-propyl}-2-methoxy-benzenesulfonic acid compound Chemical class 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 abstract 1
- 229960002613 tamsulosin Drugs 0.000 abstract 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
- C07C303/38—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 reaction of ammonia or amines with sulfonic acids, or with esters, anhydrides, or halides thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- 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
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/04—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups
- C07C303/08—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof by substitution of hydrogen atoms by sulfo or halosulfonyl groups by reaction with halogenosulfonic acids
-
- 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
- C07C303/02—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof
- C07C303/22—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of sulfonic acids or halides thereof from sulfonic acids, by reactions not involving the formation of sulfo or halosulfonyl groups; from sulfonic halides by reactions not involving the formation of halosulfonyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/49—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PT103216A PT103216B (pt) | 2004-12-06 | 2004-12-06 | Preparação de tamsulosin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE427930T1 true ATE427930T1 (de) | 2009-04-15 |
Family
ID=34959901
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT05701921T ATE427930T1 (de) | 2004-12-06 | 2005-01-18 | Verfahren zur herstellung von tamsulosin und zwischenprodukten davon |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8017803B2 (de) |
| EP (1) | EP1828110B8 (de) |
| JP (1) | JP4714222B2 (de) |
| AT (1) | ATE427930T1 (de) |
| CA (1) | CA2593010C (de) |
| DE (1) | DE602005013818D1 (de) |
| ES (1) | ES2322168T3 (de) |
| PT (1) | PT103216B (de) |
| WO (1) | WO2006061549A1 (de) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT103216B (pt) | 2004-12-06 | 2010-05-19 | Hovione Farmaciencia S A | Preparação de tamsulosin |
| CN106478467B (zh) * | 2016-10-13 | 2018-07-13 | 深圳万和制药有限公司 | 制备稳定的盐酸坦索罗辛的方法 |
| CN108465443A (zh) * | 2018-04-23 | 2018-08-31 | 新乡市锦源化工有限公司 | 对位酯的乙酰苯胺路线的生产装置及系统 |
| CN109988525B (zh) * | 2019-03-07 | 2020-12-01 | 广东省生物资源应用研究所 | 一种档案防霉驱虫胶黏剂 |
| CN111170900B (zh) * | 2020-03-18 | 2022-12-13 | 珠海润都制药股份有限公司 | 一种高光学纯度坦索罗辛杂质的制备方法 |
| CN111413435B (zh) * | 2020-04-26 | 2022-07-08 | 珠海润都制药股份有限公司 | 一种盐酸坦索罗辛中间体的检测方法 |
| CN115368278B (zh) * | 2022-10-25 | 2023-04-11 | 北京鑫开元医药科技有限公司 | 一种苯磺酰胺类化合物水解制备苯磺酸类化合物的方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000197A (en) * | 1973-07-23 | 1976-12-28 | The University Of Iowa Research Foundation | Asymmetric synthesis of phenylisopropylamines |
| JPS56110665A (en) * | 1980-02-08 | 1981-09-01 | Yamanouchi Pharmaceut Co Ltd | Sulfamoyl-substituted phenetylamine derivative and its preparation |
| US5391825A (en) * | 1980-02-08 | 1995-02-21 | Yamanouchi Pharmaceutical Co., Ltd. | Sulfamoyl substituted phenethylamine intermediates |
| JPS5813669A (ja) | 1981-07-17 | 1983-01-26 | Toshiba Corp | 冷凍機冷媒系の銅部品用表面処理剤 |
| 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 |
| KR100525493B1 (ko) | 2001-02-23 | 2005-11-02 | 연성정밀화학(주) | 설파모일 치환 페네틸아민 유도체의 제조 방법 |
| CZ20013848A3 (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 |
| ES2200699B1 (es) * | 2002-07-12 | 2005-10-01 | Ragactives, S.L | Procedimiento para la separacion de r(-) y s(+)-5-(2-((2-(etoxifenoxi)etil)amino)propil-2-metoxibenceno-sulfonamida. |
| WO2004087623A2 (en) * | 2003-03-07 | 2004-10-14 | Alembic Limited | An improved process for the preparation of (r) (-) tamsulosin hydrochloride |
| FR2864079B1 (fr) * | 2003-12-17 | 2006-04-07 | 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 |
| CZ2004197A3 (cs) * | 2004-02-05 | 2005-08-17 | Zentiva, A. S. | Způsob výroby (R)-(-)-5-(2-aminopropyl)-2-methoxybenzensulfonamidu |
| PT103216B (pt) | 2004-12-06 | 2010-05-19 | Hovione Farmaciencia S A | Preparação de tamsulosin |
-
2004
- 2004-12-06 PT PT103216A patent/PT103216B/pt not_active IP Right Cessation
-
2005
- 2005-01-18 US US11/721,028 patent/US8017803B2/en not_active Expired - Fee Related
- 2005-01-18 AT AT05701921T patent/ATE427930T1/de not_active IP Right Cessation
- 2005-01-18 DE DE602005013818T patent/DE602005013818D1/de not_active Expired - Lifetime
- 2005-01-18 WO PCT/GB2005/000155 patent/WO2006061549A1/en not_active Ceased
- 2005-01-18 CA CA2593010A patent/CA2593010C/en not_active Expired - Fee Related
- 2005-01-18 JP JP2007544965A patent/JP4714222B2/ja not_active Expired - Fee Related
- 2005-01-18 ES ES05701921T patent/ES2322168T3/es not_active Expired - Lifetime
- 2005-01-18 EP EP05701921A patent/EP1828110B8/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2593010C (en) | 2012-04-03 |
| JP2008523039A (ja) | 2008-07-03 |
| PT103216A (pt) | 2006-06-30 |
| EP1828110A1 (de) | 2007-09-05 |
| US8017803B2 (en) | 2011-09-13 |
| ES2322168T3 (es) | 2009-06-17 |
| CA2593010A1 (en) | 2006-06-15 |
| EP1828110B1 (de) | 2009-04-08 |
| JP4714222B2 (ja) | 2011-06-29 |
| EP1828110B8 (de) | 2009-07-01 |
| WO2006061549A1 (en) | 2006-06-15 |
| US20090234154A1 (en) | 2009-09-17 |
| PT103216B (pt) | 2010-05-19 |
| DE602005013818D1 (de) | 2009-05-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| RER | Ceased as to paragraph 5 lit. 3 law introducing patent treaties |