CN100430395C - 改进的皮克特-施彭格勒反应和由该反应制备得到的产物 - Google Patents

改进的皮克特-施彭格勒反应和由该反应制备得到的产物 Download PDF

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Publication number
CN100430395C
CN100430395C CNB038182386A CN03818238A CN100430395C CN 100430395 C CN100430395 C CN 100430395C CN B038182386 A CNB038182386 A CN B038182386A CN 03818238 A CN03818238 A CN 03818238A CN 100430395 C CN100430395 C CN 100430395C
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China
Prior art keywords
compound
tetrahydro
diastereomer
tryptophan
reaction
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.)
Expired - Lifetime
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CNB038182386A
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English (en)
Chinese (zh)
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CN1671706A (zh
Inventor
M·W·奥尔姆
M·J·马蒂内利
C·W·德克
J·M·帕夫拉克
E·C·切利乌斯
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A Menarini Asia Pacific Holdings Pte Ltd
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Lilly Icos LLC
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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
    • C07D471/12—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
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
  • Indole Compounds (AREA)
  • Meat, Egg Or Seafood Products (AREA)
  • Confectionery (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Dental Preparations (AREA)
CNB038182386A 2002-07-31 2003-07-14 改进的皮克特-施彭格勒反应和由该反应制备得到的产物 Expired - Lifetime CN100430395C (zh)

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
CN1671706A CN1671706A (zh) 2005-09-21
CN100430395C true CN100430395C (zh) 2008-11-05

Family

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Family Applications (1)

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CNB038182386A Expired - Lifetime CN100430395C (zh) 2002-07-31 2003-07-14 改进的皮克特-施彭格勒反应和由该反应制备得到的产物

Country Status (19)

Country Link
US (2) US7550479B2 (https=)
EP (1) EP1546149B1 (https=)
JP (2) JP2005536567A (https=)
KR (1) KR100937915B1 (https=)
CN (1) CN100430395C (https=)
AT (1) ATE415402T1 (https=)
AU (1) AU2003256539B2 (https=)
BR (1) BR0313070B1 (https=)
CA (1) CA2492540C (https=)
DE (1) DE60324949D1 (https=)
EA (1) EA008666B1 (https=)
EG (1) EG23843A (https=)
ES (1) ES2318175T3 (https=)
IL (2) IL166255A (https=)
MX (1) MXPA05001139A (https=)
NO (1) NO331775B1 (https=)
NZ (1) NZ537784A (https=)
PL (1) PL216529B1 (https=)
WO (1) WO2004011463A1 (https=)

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CN105842350A (zh) * 2015-05-14 2016-08-10 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

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KR20070072891A (ko) * 2004-11-02 2007-07-06 테바 파마슈티컬 인더스트리즈 리미티드 타달라필 결정형 및 이의 제조 방법
US7417044B2 (en) 2005-02-25 2008-08-26 Teva Pharmaceutical Industries Ltd. Tadalafil having a large particle size and a process for preparation thereof
MX2007010431A (es) * 2005-02-25 2007-10-11 Teva Pharma Proceso para purificar tadalafil.
EP1851222A1 (en) * 2005-02-25 2007-11-07 Teva Pharmaceutical Industries Ltd Process of synthesizing tadalafil
US20060276652A1 (en) * 2005-04-12 2006-12-07 Ben-Zion Dolitzky Preparation of tadalafil intermediates
WO2007052283A1 (en) * 2005-10-31 2007-05-10 Alembic Limited An improved process for preparing tadalafil and its intermediate
EP2004644A1 (en) * 2006-03-24 2008-12-24 Glenmark Pharmaceuticals Limited Process for the preparation of tadalafil
US7527912B2 (en) * 2006-09-28 2009-05-05 Shin-Etsu Chemical Co., Ltd. Photoacid generators, resist compositions, and patterning process
US20080194529A1 (en) * 2007-02-12 2008-08-14 Auspex Pharmaceuticals, Inc. HIGHLY SELECTIVE and LONG-ACTING PDE5 MODULATORS
DK2170880T3 (da) 2007-06-29 2012-09-10 Ranbaxy Lab Ltd Fremgangsmåde til fremstillingen af mellemprodukter af tetracycliske forbindelser
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
EP2673275B1 (en) * 2011-02-10 2015-04-08 Interquim, S.A. Process for obtaining compounds derived from tetrahydro-beta-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
SI3172207T1 (sl) * 2014-07-23 2019-06-28 Krka D.D., Novo Mesto Proces za pripravo zaviralca CGMP-fosfodiesteraze in oralne farmacevtske formulacije, ki obsega koprecipitate tadalafila
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
US12129265B2 (en) 2020-07-21 2024-10-29 Ankh Life Sciences Limited Therapeutic agents and uses thereof
CN114057738A (zh) * 2021-12-14 2022-02-18 京博农化科技有限公司 一种氯吲哚酰肼的合成方法
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
CN116715667A (zh) * 2023-06-20 2023-09-08 常州制药厂有限公司 一种他达拉非新晶型b及其制备方法

Citations (3)

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US5859006A (en) * 1994-01-21 1999-01-12 Icos Corporation Tetracyclic derivatives; process of preparation and use
US5981527A (en) * 1995-07-14 1999-11-09 Icos Corporation Cyclic GMP-specific phosphodiesterase inhibitors
US6001847A (en) * 1995-07-14 1999-12-14 Icos Corporation Chemical compounds

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ATE337320T1 (de) * 2000-11-06 2006-09-15 Lilly Icos Llc Indolderivate als pde5-inhibitoren
ES2307758T3 (es) * 2001-06-05 2008-12-01 Lilly Icos Llc Derivados de pirazino (1',2':1,6)pirido(3,4-b)indol 1,4-diona.

Patent Citations (3)

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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
US5981527A (en) * 1995-07-14 1999-11-09 Icos Corporation Cyclic GMP-specific phosphodiesterase inhibitors
US6001847A (en) * 1995-07-14 1999-12-14 Icos Corporation Chemical compounds

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
"Diastereo- and enantioselectivity in the Pictet-Spenglerreaction". BAILEY P D ET AL.J CHEM SOC PERKIN TRANS,Vol.1 No.4. 1999 *
The fate of the tryptophan stereocenter in the synthesis of 7,10,16,16a-tetrahydro-11H-quinazolina[2',3':3,4]-pyrazino[1,2-b]β-carboline-5,8-diones". MADRIGAL, A. ET AL.Tetrahedron:Asymmetry,Vol.11. 2000 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105842350A (zh) * 2015-05-14 2016-08-10 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

Also Published As

Publication number Publication date
NO331775B1 (no) 2012-03-26
EA008666B1 (ru) 2007-06-29
EA200500264A1 (ru) 2005-08-25
ES2318175T3 (es) 2009-05-01
IL200692A (en) 2011-11-30
CA2492540A1 (en) 2004-02-05
US20060004203A1 (en) 2006-01-05
KR100937915B1 (ko) 2010-01-21
JP2009235096A (ja) 2009-10-15
AU2003256539A1 (en) 2004-02-16
CN1671706A (zh) 2005-09-21
EG23843A (en) 2007-10-17
US20090312548A1 (en) 2009-12-17
BR0313070B1 (pt) 2014-09-09
IL166255A0 (en) 2006-01-15
CA2492540C (en) 2010-05-04
DE60324949D1 (de) 2009-01-08
AU2003256539B2 (en) 2010-03-04
BR0313070A (pt) 2005-06-28
NZ537784A (en) 2008-01-31
US7550479B2 (en) 2009-06-23
MXPA05001139A (es) 2005-05-16
EP1546149A1 (en) 2005-06-29
IL166255A (en) 2010-04-29
JP4994427B2 (ja) 2012-08-08
JP2005536567A (ja) 2005-12-02
KR20050030961A (ko) 2005-03-31
PL375092A1 (en) 2005-11-14
IL200692A0 (en) 2010-05-17
EP1546149B1 (en) 2008-11-26
PL216529B1 (pl) 2014-04-30
NO20051022L (no) 2005-04-22
WO2004011463A1 (en) 2004-02-05
ATE415402T1 (de) 2008-12-15

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Owner name: ICOS CORP.

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Patentee after: Icos Corp.

Address before: The United States Delaware

Patentee before: Lilly Icos LLC

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Patentee after: A. menarini Asia Pacific Holdings Pte. Ltd.

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Patentee before: ICOS Corp.

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Granted publication date: 20081105

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