KR100937915B1 - 변형된 픽텟-스펭글러 반응 및 그것으로부터 제조된생성물 - Google Patents
변형된 픽텟-스펭글러 반응 및 그것으로부터 제조된생성물 Download PDFInfo
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- KR100937915B1 KR100937915B1 KR1020057001520A KR20057001520A KR100937915B1 KR 100937915 B1 KR100937915 B1 KR 100937915B1 KR 1020057001520 A KR1020057001520 A KR 1020057001520A KR 20057001520 A KR20057001520 A KR 20057001520A KR 100937915 B1 KR100937915 B1 KR 100937915B1
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- 0 COC([C@@](CC(c1ccccc1*CC1)=C1[C@]1c(cc2)cc3c2OCO3)N1C(CCl)=O)=O Chemical compound COC([C@@](CC(c1ccccc1*CC1)=C1[C@]1c(cc2)cc3c2OCO3)N1C(CCl)=O)=O 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Meat, Egg Or Seafood Products (AREA)
- Confectionery (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Dental Preparations (AREA)
Abstract
Description
Claims (23)
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- 하기 화학식을 갖는 테트라하이드로-β-카르볼린의 시스-부분입체 이성체를 제조하는 방법으로서,(a) 화학식 R2OH(식중, R2는 메틸, 에틸, 이소프로필, n-프로필, n-부틸, sec-부틸, t-부틸 및 이의 혼합물로 구성되는 군으로부터 선택됨)를 갖는 알콜을 사용하여 에스테르화한 트립토판을 제공하는 단계;(b) 단계 (a)의 트립토판 에스테르와 화학식 R1CHO(식중, R1은 아릴기 또는 지방족기임)를 갖는 지방족 또는 아릴 알데히드를 반응시켜 시스-부분입체 이성체 및 원하지 않는 부분입체 이성체를 제공하는 단계로서, 상기 반응은 알콜인 용매에서 수행되는 단계; 및(c) 가용성의 원하지 않는 부분입체 이성체로부터 불용성의 시스-부분입체 이성체를 분리하는 단계를 포함하는 방법.
- 제9항에 있어서, 단계 (b)의 알콜이 이소프로필 알콜, n-프로필 알콜, n-부탄올 및 sec-부틸 알콜로 구성되는 군으로부터 선택되는 것인 방법.
- 제9항에 있어서, 단계 (b)의 알콜이 이소프로필 알콜인 방법.
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- 하기 구조식을 갖는 화합물을 제조하는 방법으로서,(a) 메탄올과 티오닐 클로라이드 중에서 D-트립토판을 에스테르화하여 D-트립토판 메틸 에스테르 염산염을 제공하는 단계;(b) D-트립토판 메틸 에스테르 염산염과 피페로날을 환류 이소-프로필 알콜 중에서 반응시켜 시스-1-(1,3-벤조디옥솔-5-일)-2,3,4,9-테트라하이드로-1H-피리도[3,4-b]인돌-3-카르복실산 메틸 에스테르를 제공하는 단계;(c) 단계 (b)의 생성물과 클로로아세틸 클로라이드 및 트리에틸아민을 반응시켜 하기 화합물을 제공하는 단계; 및(d) 단계 (c)의 생성물을 메틸아민과 반응시켜 목적하는 화합물을 제공하는 단계를 포함하는 방법.
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Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US40038602P | 2002-07-31 | 2002-07-31 | |
US60/400,386 | 2002-07-31 | ||
US46016103P | 2003-04-03 | 2003-04-03 | |
US60/460,161 | 2003-04-03 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR20050030961A KR20050030961A (ko) | 2005-03-31 |
KR100937915B1 true KR100937915B1 (ko) | 2010-01-21 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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KR1020057001520A KR100937915B1 (ko) | 2002-07-31 | 2003-07-14 | 변형된 픽텟-스펭글러 반응 및 그것으로부터 제조된생성물 |
Country Status (19)
Country | Link |
---|---|
US (2) | US7550479B2 (ko) |
EP (1) | EP1546149B1 (ko) |
JP (2) | JP2005536567A (ko) |
KR (1) | KR100937915B1 (ko) |
CN (1) | CN100430395C (ko) |
AT (1) | ATE415402T1 (ko) |
AU (1) | AU2003256539B2 (ko) |
BR (1) | BR0313070B1 (ko) |
CA (1) | CA2492540C (ko) |
DE (1) | DE60324949D1 (ko) |
EA (1) | EA008666B1 (ko) |
EG (1) | EG23843A (ko) |
ES (1) | ES2318175T3 (ko) |
IL (2) | IL166255A (ko) |
MX (1) | MXPA05001139A (ko) |
NO (1) | NO331775B1 (ko) |
NZ (1) | NZ537784A (ko) |
PL (1) | PL216529B1 (ko) |
WO (1) | WO2004011463A1 (ko) |
Families Citing this family (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2005116030A1 (en) * | 2004-05-31 | 2005-12-08 | Matrix Laboratories Ltd | A process for the preparation of tadalafil |
EP1804582A4 (en) * | 2004-10-28 | 2009-12-09 | Reddys Lab Ltd Dr | POLYMORPH SHAPES OF TADALAFIL |
EP1799216A2 (en) * | 2004-11-02 | 2007-06-27 | Teva Pharmaceutical Industries Ltd | Tadalafil crystal forms and processes for preparing them |
CA2599378A1 (en) * | 2005-02-25 | 2006-08-31 | Teva Pharmaceutical Industries Ltd. | Tadalafil having a large particle size and a process for preparation thereof |
US20070004737A1 (en) * | 2005-02-25 | 2007-01-04 | Inbal Ornan | Process of purifying tadalafil |
WO2006091975A1 (en) * | 2005-02-25 | 2006-08-31 | Teva Pharmaceutical Industries Ltd. | Process of synthesizing tadalafil |
CN101155809A (zh) * | 2005-04-12 | 2008-04-02 | 特瓦制药工业有限公司 | 他达那非中间体的制备 |
WO2007052283A1 (en) * | 2005-10-31 | 2007-05-10 | Alembic Limited | An improved process for preparing tadalafil and its intermediate |
WO2007110734A1 (en) * | 2006-03-24 | 2007-10-04 | Glenmark Pharmaceuticals Limited | Process for the preparation of tadalafil |
KR101035742B1 (ko) * | 2006-09-28 | 2011-05-20 | 신에쓰 가가꾸 고교 가부시끼가이샤 | 신규 광산 발생제 및 이것을 이용한 레지스트 재료 및 패턴형성 방법 |
US20080194529A1 (en) * | 2007-02-12 | 2008-08-14 | Auspex Pharmaceuticals, Inc. | HIGHLY SELECTIVE and LONG-ACTING PDE5 MODULATORS |
US8445698B2 (en) | 2007-06-29 | 2013-05-21 | Ranbaxy Laboratories Limited | Process for the preparation of an intermediate of tadalafil |
ITMI20080285A1 (it) | 2008-02-22 | 2009-08-23 | Endura Spa | Procedimento per la preparazione di esteri di acidi tetraidro-1h-betacarbolin-3-carbossilici |
EP2107059A1 (en) | 2008-03-31 | 2009-10-07 | LEK Pharmaceuticals D.D. | Conversion of tryptophan into ß-carboline derivatives |
PL385356A1 (pl) | 2008-06-03 | 2009-12-07 | Zakłady Farmaceutyczne POLPHARMA Spółka Akcyjna | Sposób wytwarzania tadalafilu |
CN101906103A (zh) * | 2010-08-08 | 2010-12-08 | 浙江华海药业股份有限公司 | 四氢-β-咔啉化合物合成方法的改进 |
US8829023B2 (en) | 2011-02-10 | 2014-09-09 | Interquim, S.A. | Process for obtaining compounds derived from tetrahydro-β-carboline |
CN102367253B (zh) * | 2011-09-20 | 2016-04-06 | 浙江华海药业股份有限公司 | 一种制备他达拉非晶型a的方法 |
AR099416A1 (es) | 2014-02-28 | 2016-07-20 | Lilly Co Eli | Terapia combinada para la hipertensión resistente |
CN103980275B (zh) * | 2014-05-14 | 2016-09-28 | 湖北省医药工业研究院有限公司 | 磷酸二酯酶5抑制剂他达拉非的制备方法 |
CN104151313B (zh) * | 2014-07-13 | 2019-04-09 | 浙江华海药业股份有限公司 | 一种纯化他达拉非中间体的方法 |
WO2016012539A1 (en) * | 2014-07-23 | 2016-01-28 | Krka, D.D., Novo Mesto | A process for the preparation of cgmp-phosphodiesterase inhibitor and oral pharmaceutical formulation comprising tadalafil co-precipitates |
CN105842350B (zh) * | 2015-05-14 | 2018-11-13 | 湖北生物医药产业技术研究院有限公司 | 利用高效液相色谱分析他达拉非合成中间体的方法 |
CN105061428B (zh) * | 2015-08-26 | 2019-12-27 | 浙江华海药业股份有限公司 | 一种精制他达拉非的方法 |
CN106674223A (zh) * | 2016-06-29 | 2017-05-17 | 浙江华海药业股份有限公司 | 一种精制他达拉非的方法 |
CN107663210A (zh) * | 2016-07-28 | 2018-02-06 | 常州爱诺新睿医药技术有限公司 | 一种新的制备无水他达拉非晶型i的方法 |
CN106279155B (zh) * | 2016-08-02 | 2019-03-19 | 扬子江药业集团四川海蓉药业有限公司 | 他达拉非的杂质对照品及其制备方法 |
CN109053724A (zh) * | 2018-08-22 | 2018-12-21 | 上海青平药业有限公司 | 一种制备他达拉非过程中的杂质及该杂质的制备方法和他达拉非的纯化方法以及用途 |
CN110437228B (zh) * | 2019-07-22 | 2022-06-14 | 山东省药学科学院 | 一种他达拉非及其中间体的制备方法 |
US10947253B2 (en) | 2019-08-05 | 2021-03-16 | Ankh Life Sciences Limited | Fused polycyclic dimers |
CN110790764B (zh) * | 2019-11-27 | 2021-04-06 | 四川省通园制药集团有限公司 | 一种一锅法制备他达拉非的方法 |
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CN114805345B (zh) * | 2022-04-27 | 2023-11-10 | 山东省药学科学院 | 一种他达拉非中间体顺式四氢咔啉盐酸盐的制备方法 |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5859006A (en) * | 1994-01-21 | 1999-01-12 | Icos Corporation | Tetracyclic derivatives; process of preparation and use |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9514465D0 (en) * | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Chemical compounds |
GB9514473D0 (en) * | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Chemical compounds |
AU2002211493A1 (en) * | 2000-11-06 | 2002-05-15 | Lilly Icos Llc | Indole derivatives as pde5-inhibitors |
EP1392688B1 (en) * | 2001-06-05 | 2008-06-04 | Lilly Icos LLC | Pyrazino[1',2':1,6]-pyrido[3,4-b] indole-1,4-dione derivatives |
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2003
- 2003-07-14 EP EP03771620A patent/EP1546149B1/en not_active Expired - Lifetime
- 2003-07-14 DE DE60324949T patent/DE60324949D1/de not_active Expired - Lifetime
- 2003-07-14 BR BRPI0313070-3A patent/BR0313070B1/pt not_active IP Right Cessation
- 2003-07-14 NZ NZ537784A patent/NZ537784A/en not_active IP Right Cessation
- 2003-07-14 AU AU2003256539A patent/AU2003256539B2/en not_active Expired
- 2003-07-14 ES ES03771620T patent/ES2318175T3/es not_active Expired - Lifetime
- 2003-07-14 AT AT03771620T patent/ATE415402T1/de not_active IP Right Cessation
- 2003-07-14 WO PCT/US2003/022039 patent/WO2004011463A1/en active Application Filing
- 2003-07-14 US US10/521,393 patent/US7550479B2/en active Active
- 2003-07-14 KR KR1020057001520A patent/KR100937915B1/ko active IP Right Grant
- 2003-07-14 CN CNB038182386A patent/CN100430395C/zh not_active Expired - Lifetime
- 2003-07-14 EA EA200500264A patent/EA008666B1/ru unknown
- 2003-07-14 CA CA2492540A patent/CA2492540C/en not_active Expired - Lifetime
- 2003-07-14 MX MXPA05001139A patent/MXPA05001139A/es active IP Right Grant
- 2003-07-14 PL PL375092A patent/PL216529B1/pl unknown
- 2003-07-14 JP JP2005505597A patent/JP2005536567A/ja active Pending
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2005
- 2005-01-12 IL IL166255A patent/IL166255A/en active IP Right Grant
- 2005-01-29 EG EGNA2005000016 patent/EG23843A/xx active
- 2005-02-25 NO NO20051022A patent/NO331775B1/no not_active IP Right Cessation
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2009
- 2009-06-18 US US12/486,817 patent/US20090312548A1/en not_active Abandoned
- 2009-07-15 JP JP2009166570A patent/JP4994427B2/ja not_active Expired - Lifetime
- 2009-09-02 IL IL200692A patent/IL200692A/en active IP Right Grant
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5859006A (en) * | 1994-01-21 | 1999-01-12 | Icos Corporation | Tetracyclic derivatives; process of preparation and use |
Non-Patent Citations (1)
Title |
---|
Journal of Chemical Society Perkin Transaction 1, 431-439, (1993.)* |
Also Published As
Publication number | Publication date |
---|---|
BR0313070A (pt) | 2005-06-28 |
IL200692A (en) | 2011-11-30 |
ES2318175T3 (es) | 2009-05-01 |
NO20051022L (no) | 2005-04-22 |
PL216529B1 (pl) | 2014-04-30 |
JP2005536567A (ja) | 2005-12-02 |
NZ537784A (en) | 2008-01-31 |
US7550479B2 (en) | 2009-06-23 |
JP2009235096A (ja) | 2009-10-15 |
EG23843A (en) | 2007-10-17 |
EA008666B1 (ru) | 2007-06-29 |
CA2492540A1 (en) | 2004-02-05 |
MXPA05001139A (es) | 2005-05-16 |
IL200692A0 (en) | 2010-05-17 |
EP1546149B1 (en) | 2008-11-26 |
CN100430395C (zh) | 2008-11-05 |
JP4994427B2 (ja) | 2012-08-08 |
BR0313070B1 (pt) | 2014-09-09 |
KR20050030961A (ko) | 2005-03-31 |
PL375092A1 (en) | 2005-11-14 |
US20060004203A1 (en) | 2006-01-05 |
ATE415402T1 (de) | 2008-12-15 |
NO331775B1 (no) | 2012-03-26 |
EA200500264A1 (ru) | 2005-08-25 |
CA2492540C (en) | 2010-05-04 |
EP1546149A1 (en) | 2005-06-29 |
WO2004011463A1 (en) | 2004-02-05 |
AU2003256539B2 (en) | 2010-03-04 |
IL166255A0 (en) | 2006-01-15 |
IL166255A (en) | 2010-04-29 |
AU2003256539A1 (en) | 2004-02-16 |
CN1671706A (zh) | 2005-09-21 |
US20090312548A1 (en) | 2009-12-17 |
DE60324949D1 (de) | 2009-01-08 |
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