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WO2006060225A3 - Process for asymmetric synthesis of hexahydropyrimido[1,2-a] azepine-2-carboxamides and related compounds - Google Patents

Process for asymmetric synthesis of hexahydropyrimido[1,2-a] azepine-2-carboxamides and related compounds Download PDF

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Publication number
WO2006060225A3
WO2006060225A3 PCT/US2005/042211 US2005042211W WO2006060225A3 WO 2006060225 A3 WO2006060225 A3 WO 2006060225A3 US 2005042211 W US2005042211 W US 2005042211W WO 2006060225 A3 WO2006060225 A3 WO 2006060225A3
Authority
WO
WIPO (PCT)
Prior art keywords
carboxamides
hexahydropyrimido
azepine
related compounds
asymmetric synthesis
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.)
Ceased
Application number
PCT/US2005/042211
Other languages
French (fr)
Other versions
WO2006060225A2 (en
Inventor
Yong-Li Zhong
Shane W Krska
Jaemoon Lee
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Merck and Co Inc filed Critical Merck and Co Inc
Publication of WO2006060225A2 publication Critical patent/WO2006060225A2/en
Publication of WO2006060225A3 publication Critical patent/WO2006060225A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Processes for asymmetric synthesis of 1O(S)-amino-3-hydroxy-4-oxo-4,6,7,8,9,10­hexahydropyrimido[1,2-a]azepine-2-carboxamides and related compounds are disclosed. The enantiomerically enriched carboxamides are useful as HIV integrase inhibitors and thus are useful for treating HIV infection and AIDS.
PCT/US2005/042211 2004-11-23 2005-11-18 Process for asymmetric synthesis of hexahydropyrimido[1,2-a] azepine-2-carboxamides and related compounds Ceased WO2006060225A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US63032204P 2004-11-23 2004-11-23
US60/630,322 2004-11-23

Publications (2)

Publication Number Publication Date
WO2006060225A2 WO2006060225A2 (en) 2006-06-08
WO2006060225A3 true WO2006060225A3 (en) 2006-10-12

Family

ID=36216789

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2005/042211 Ceased WO2006060225A2 (en) 2004-11-23 2005-11-18 Process for asymmetric synthesis of hexahydropyrimido[1,2-a] azepine-2-carboxamides and related compounds

Country Status (1)

Country Link
WO (1) WO2006060225A2 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2662419A1 (en) * 2006-09-15 2008-03-20 Stefan Abrecht Process for the preparation of pyrido[2,1-a]isoquinoline derivatives by catalytic asymmetric hydrogenation of an enamine
WO2008123067A1 (en) * 2007-03-19 2008-10-16 Takeda Pharmaceutical Company Limited Method for asymmetric hydrogenation of allyl amine
CN102239172A (en) * 2008-10-06 2011-11-09 默沙东公司 Hiv integrase inhibitors
US9227901B2 (en) * 2012-07-05 2016-01-05 Abbvie Inc. Process for preparing bicyclic amine derivatives
WO2014008636A1 (en) * 2012-07-11 2014-01-16 Merck Sharp & Dohme Corp. Macrocyclic compounds as hiv integrase inhibitors
CN115677579B (en) * 2022-11-02 2024-05-24 上海药坦药物研究开发有限公司 Preparation method of tetrahydropapaverine and intermediate thereof

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1386901A1 (en) * 2002-07-30 2004-02-04 Takasago International Corporation Method for producing an optically active beta-amino acid
WO2004058757A1 (en) * 2002-12-27 2004-07-15 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa Tetrahydro-4h-pyrido[1,2-a]pyrimidines and related compounds useful as hiv integrase inhibitors
WO2005061501A2 (en) * 2003-12-12 2005-07-07 Merck & Co., Inc. Process for preparing hexahydropyrimido[1,2-a]azepine-2-carboxylates and related compounds

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1386901A1 (en) * 2002-07-30 2004-02-04 Takasago International Corporation Method for producing an optically active beta-amino acid
WO2004058757A1 (en) * 2002-12-27 2004-07-15 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa Tetrahydro-4h-pyrido[1,2-a]pyrimidines and related compounds useful as hiv integrase inhibitors
WO2005061501A2 (en) * 2003-12-12 2005-07-07 Merck & Co., Inc. Process for preparing hexahydropyrimido[1,2-a]azepine-2-carboxylates and related compounds

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
RINGWALD M ET AL: "ASYMMETRIC THERMAL TRANSFORMATION, A NEW WAY TO ENANTIOPURE BIPHENYL-BRIDGED TITANOCENE AND ZIRCONOCENE COMPLEXES: EFFICIENT CATALYSTS FOR ASYMMETRIC IMINE HYDROGENATION", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 121, no. 7, 1999, pages 1524 - 1527, XP000962051, ISSN: 0002-7863 *
YI HSIAO ET AL: "Highly Efficient Synthesis of beta-Amino Acid Derivatives via Asymmetric Hydrogenation of Unprotected Enamines", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 126, no. 32, 21 July 2004 (2004-07-21), pages 9918 - 9919, XP002339712, ISSN: 0002-7863 *

Also Published As

Publication number Publication date
WO2006060225A2 (en) 2006-06-08

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