WO2009013764A3 - Process for producing 6(r)-[2-(8'(s)-2 ',2 '-dimethylbutyryloxy-2'(s),6'(r)-dimethyl-1,2,6,7', 8',8a'(r)- hexahydronaphthyl-l'(s))ethyl]-4(r)-hydroxy-3,4,5,6- tetrahydro-2h-pyran-2-one - Google Patents

Process for producing 6(r)-[2-(8'(s)-2 ',2 '-dimethylbutyryloxy-2'(s),6'(r)-dimethyl-1,2,6,7', 8',8a'(r)- hexahydronaphthyl-l'(s))ethyl]-4(r)-hydroxy-3,4,5,6- tetrahydro-2h-pyran-2-one Download PDF

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Publication number
WO2009013764A3
WO2009013764A3 PCT/IN2008/000467 IN2008000467W WO2009013764A3 WO 2009013764 A3 WO2009013764 A3 WO 2009013764A3 IN 2008000467 W IN2008000467 W IN 2008000467W WO 2009013764 A3 WO2009013764 A3 WO 2009013764A3
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WO
WIPO (PCT)
Prior art keywords
dimethyl
ethyl
dimethylbutyryloxy
hexahydronaphthyl
pyran
Prior art date
Application number
PCT/IN2008/000467
Other languages
French (fr)
Other versions
WO2009013764A2 (en
Inventor
Harnam Singh
Shailendra Kumar Dubey
Nitin Gupta
Sushil Kumar Dubey
Original Assignee
Jubilant Organosys Ltd
Harnam Singh
Shailendra Kumar Dubey
Nitin Gupta
Sushil Kumar Dubey
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 Jubilant Organosys Ltd, Harnam Singh, Shailendra Kumar Dubey, Nitin Gupta, Sushil Kumar Dubey filed Critical Jubilant Organosys Ltd
Publication of WO2009013764A2 publication Critical patent/WO2009013764A2/en
Publication of WO2009013764A3 publication Critical patent/WO2009013764A3/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D309/30—Oxygen atoms, e.g. delta-lactones

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pyrane Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Disclosed herein is an improved process for producing HMG-CoA reductase inhibitor, 6(R)-[2-(8 '(S)-2 ',2 ''-dimethylbutyryloxy-2'(S),6 '(R)-dimethyl- 1', 2', 6', 7', 8',8a'(R)-hexahydronaphthyl-r(S))ethyl]-4(R)-hydroxy-3,4,5,6-tetrahydro-2H- pyran-2-one, the process comprising hydrolyzing (lS,3R,7S,8S,8aR)-8-{2-[(2R,4R)- 4-hydroxy-6-oxotetrahydro-2H-ρyran-2-yl]ethyl}-3,7-dimethyl-l,2,3,7,8,8a- hexahydronaphthalen-1-yl (2S)-2-methylbutanoate in presence of a base and antioxidant, lactonizing and selectively protecting the hydroxyl group of the resultant compound, followed by acylation with an acylating agent to obtain 6(R)-[2-(8'(S)- 2',2''-dimethylbutyryloxy-2 '(S),6 '(R)-dimethyl- 1',2',6',7',8',8a'(R)- hexahydronaphthyl-r(S))ethyl]-4(R)-substituted)-3,4,5,6-tetrahydro-2H-pyran-2-one and further deprotection to obtain 6(R)-[2-(8'(S)-2',2'-dimethylbutyryloxy- 2'(S),6'(R)-dimethyl-1',2',6',7',8',8a'(R)-hexahydronaphthyl-1'(S))ethyl]-4(R)- hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-one.
PCT/IN2008/000467 2007-07-24 2008-07-24 Process for producing 6(r)-[2-(8'(s)-2 ',2 '-dimethylbutyryloxy-2'(s),6'(r)-dimethyl-1,2,6,7', 8',8a'(r)- hexahydronaphthyl-l'(s))ethyl]-4(r)-hydroxy-3,4,5,6- tetrahydro-2h-pyran-2-one WO2009013764A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN1554DE2007 2007-07-24
IN1554/DEL/2007 2007-07-24

Publications (2)

Publication Number Publication Date
WO2009013764A2 WO2009013764A2 (en) 2009-01-29
WO2009013764A3 true WO2009013764A3 (en) 2009-03-19

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IN2008/000467 WO2009013764A2 (en) 2007-07-24 2008-07-24 Process for producing 6(r)-[2-(8'(s)-2 ',2 '-dimethylbutyryloxy-2'(s),6'(r)-dimethyl-1,2,6,7', 8',8a'(r)- hexahydronaphthyl-l'(s))ethyl]-4(r)-hydroxy-3,4,5,6- tetrahydro-2h-pyran-2-one

Country Status (1)

Country Link
WO (1) WO2009013764A2 (en)

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0033538A2 (en) * 1980-02-04 1981-08-12 Merck & Co. Inc. 6(R)-(2-(8'-acyloxy-2'-methyl-6'-methyl (or hydrogen)-polyhydronaphthyl-1')-ethyl)-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-ones, the hydroxy acid form of said pyranones, the pharmaceutically acceptable salts of said hydroxy acids, and the lower alkyl, and phenyl, dimethylamino or acetylamino substituted lower alkyl esters of said hydroxy acid, processes for preparing the same, and a pharmaceutical antihypercholesterolemic composition containing the same
US4444784A (en) * 1980-08-05 1984-04-24 Merck & Co., Inc. Antihypercholesterolemic compounds
WO1997020834A1 (en) * 1995-12-06 1997-06-12 Antibiotic Co. Method of production of lovastatin
WO2001045484A2 (en) * 2001-02-27 2001-06-28 Chong Kun Dang Pharmaceutical Corp. An improved process for preparing simvastatin
WO2003057684A1 (en) * 2002-01-09 2003-07-17 Hanmi Pharm. Co., Ltd. Process for the preparation of simvastatin
WO2005058861A1 (en) * 2003-12-16 2005-06-30 Uk Chemipharm Co., Ltd. Process for preparing simvastatin.
WO2005077928A1 (en) * 2004-02-12 2005-08-25 Jubilant Organosys Limited Improved process for producing simvastatin
US20070117996A1 (en) * 2005-11-21 2007-05-24 Srinivasulu Gudipati Process for preparing simvastatin

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0033538A2 (en) * 1980-02-04 1981-08-12 Merck & Co. Inc. 6(R)-(2-(8'-acyloxy-2'-methyl-6'-methyl (or hydrogen)-polyhydronaphthyl-1')-ethyl)-4(R)-hydroxy-3,4,5,6-tetrahydro-2H-pyran-2-ones, the hydroxy acid form of said pyranones, the pharmaceutically acceptable salts of said hydroxy acids, and the lower alkyl, and phenyl, dimethylamino or acetylamino substituted lower alkyl esters of said hydroxy acid, processes for preparing the same, and a pharmaceutical antihypercholesterolemic composition containing the same
US4444784A (en) * 1980-08-05 1984-04-24 Merck & Co., Inc. Antihypercholesterolemic compounds
WO1997020834A1 (en) * 1995-12-06 1997-06-12 Antibiotic Co. Method of production of lovastatin
WO2001045484A2 (en) * 2001-02-27 2001-06-28 Chong Kun Dang Pharmaceutical Corp. An improved process for preparing simvastatin
WO2003057684A1 (en) * 2002-01-09 2003-07-17 Hanmi Pharm. Co., Ltd. Process for the preparation of simvastatin
WO2005058861A1 (en) * 2003-12-16 2005-06-30 Uk Chemipharm Co., Ltd. Process for preparing simvastatin.
WO2005077928A1 (en) * 2004-02-12 2005-08-25 Jubilant Organosys Limited Improved process for producing simvastatin
US20070117996A1 (en) * 2005-11-21 2007-05-24 Srinivasulu Gudipati Process for preparing simvastatin

Also Published As

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WO2009013764A2 (en) 2009-01-29

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