WO2009084827A3 - Synthetic intermediates, process for preparing pyrrolylheptanoic acid derivatives therefrom - Google Patents

Synthetic intermediates, process for preparing pyrrolylheptanoic acid derivatives therefrom Download PDF

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Publication number
WO2009084827A3
WO2009084827A3 PCT/KR2008/007350 KR2008007350W WO2009084827A3 WO 2009084827 A3 WO2009084827 A3 WO 2009084827A3 KR 2008007350 W KR2008007350 W KR 2008007350W WO 2009084827 A3 WO2009084827 A3 WO 2009084827A3
Authority
WO
WIPO (PCT)
Prior art keywords
pyrrolylheptanoic
derivative
acid derivatives
fluorphenyl
isopropyl
Prior art date
Application number
PCT/KR2008/007350
Other languages
French (fr)
Other versions
WO2009084827A2 (en
Inventor
Moon-Sung Kim
Moo-Hi Yoo
Jae-Keol Rhee
Yong-Jik Kim
Seong-Jin Park
Jun-Ho Choi
Si-Young Sung
Hong-Gyu Lim
Dae-Won Cha
Original Assignee
Dong-A Pharm.Co., Ltd.
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 Dong-A Pharm.Co., Ltd. filed Critical Dong-A Pharm.Co., Ltd.
Priority to JP2010540562A priority Critical patent/JP2011507947A/en
Publication of WO2009084827A2 publication Critical patent/WO2009084827A2/en
Publication of WO2009084827A3 publication Critical patent/WO2009084827A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
    • C07D207/36—Oxygen or sulfur atoms
    • C07D207/40—2,5-Pyrrolidine-diones
    • C07D207/416—2,5-Pyrrolidine-diones 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 other ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C07D207/333—Radicals substituted by oxygen or sulfur atoms

Abstract

There are provided intermediates used to prepare a derivative, (3R,5R)-7-[2-(4-fluorphenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-lH-pyrrol-l-yl]-3,5-di hydroxyheptanoic acid, which has an effect to suppress cholesterol in blood, and a process for preparing pyrrolylheptanoic acid derivatives therefrom. In accordance with the present invention, the 5-(4-fluorphenyl)-2-isopropyl-4-phenyl-lH-pyrrole-3-carbonyl derivative is provided as one of the novel synthetic intermediates that are used to prepare pyrrolylheptanoic acid derivatives including a derivative, (3R,5R)-7-[2-(4-fluorphenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-lH-pyrrol-l-yl]-3,5-di hydroxyheptanoic acid. Therefore, the (3R,5R)-7-[2-(4-fluorphenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-lH-pyrrol-l-yl]-3,5-di hydroxyheptanoic acid derivative may be prepared from the carbonyl derivative in a high yield for a short time period under a moderate condition.
PCT/KR2008/007350 2007-12-27 2008-12-12 Synthetic intermediates, process for preparing pyrrolylheptanoic acid derivatives therefrom WO2009084827A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2010540562A JP2011507947A (en) 2007-12-27 2008-12-12 A production method using a synthetic intermediate of a pyrrolylheptanoic acid derivative and a novel synthetic intermediate.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2007-0138166 2007-12-27
KR1020070138166A KR20090070233A (en) 2007-12-27 2007-12-27 Synthetic intermediates, process for preparing pyrrolylheptanoic acid derivatives therefrom

Publications (2)

Publication Number Publication Date
WO2009084827A2 WO2009084827A2 (en) 2009-07-09
WO2009084827A3 true WO2009084827A3 (en) 2009-08-27

Family

ID=40824861

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2008/007350 WO2009084827A2 (en) 2007-12-27 2008-12-12 Synthetic intermediates, process for preparing pyrrolylheptanoic acid derivatives therefrom

Country Status (3)

Country Link
JP (1) JP2011507947A (en)
KR (1) KR20090070233A (en)
WO (1) WO2009084827A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102617440B (en) * 2012-03-07 2013-11-06 湖南欧亚生物有限公司 Method for preparing atorvastatin calcium
CN102702014B (en) * 2012-05-28 2014-03-19 扬子江药业集团江苏海慈生物药业有限公司 Method for preparing atorvastatin calcium intermediate
CN104151286B (en) * 2014-04-10 2018-05-15 湖北益泰药业有限公司 A kind of method prepared by Atorvastatin calcium intermediate

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050182125A1 (en) * 2003-05-16 2005-08-18 Ambit Biosciences Corporation Pyrrole compounds and uses thereof
WO2006110918A1 (en) * 2005-04-13 2006-10-19 Ambit Biosciences Corporation Pyrrole compounds and uses thereof
EP1834944A1 (en) * 2006-03-17 2007-09-19 Ratiopharm GmbH Process for preparing C7 intermediates and their use in the preparation on N-substituted pyrrole derivatives

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007516227A (en) * 2003-05-16 2007-06-21 アンビット バイオサイエンシス コーポレーション Pyrrole compounds and uses thereof

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050182125A1 (en) * 2003-05-16 2005-08-18 Ambit Biosciences Corporation Pyrrole compounds and uses thereof
WO2006110918A1 (en) * 2005-04-13 2006-10-19 Ambit Biosciences Corporation Pyrrole compounds and uses thereof
EP1834944A1 (en) * 2006-03-17 2007-09-19 Ratiopharm GmbH Process for preparing C7 intermediates and their use in the preparation on N-substituted pyrrole derivatives

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
PRAMOD. S. PANDEY ET AL.: "An efficient synthesis ofN3,4-diphenyl-5-(4- fluorophenyl)-2-isopropyl-1H-3-pyrrolecarboxamide, a key intermediate for atorvastatin synthesis.", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS., vol. 14, no. 1, 2004, pages 129 - 131 *

Also Published As

Publication number Publication date
WO2009084827A2 (en) 2009-07-09
KR20090070233A (en) 2009-07-01
JP2011507947A (en) 2011-03-10

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