WO2008084671A1 - Process for producing 1-substituted-2-pyridone-3-carboxylic acid derivative - Google Patents

Process for producing 1-substituted-2-pyridone-3-carboxylic acid derivative Download PDF

Info

Publication number
WO2008084671A1
WO2008084671A1 PCT/JP2007/074791 JP2007074791W WO2008084671A1 WO 2008084671 A1 WO2008084671 A1 WO 2008084671A1 JP 2007074791 W JP2007074791 W JP 2007074791W WO 2008084671 A1 WO2008084671 A1 WO 2008084671A1
Authority
WO
WIPO (PCT)
Prior art keywords
pyridone
producing
substituted
general formula
compound represented
Prior art date
Application number
PCT/JP2007/074791
Other languages
French (fr)
Japanese (ja)
Inventor
Tomohiro Unno
Junichi Morita
Shoji Shinomoto
Yoshihide Sugata
Yutaka Ide
Original Assignee
Shionogi & 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 Shionogi & Co., Ltd. filed Critical Shionogi & Co., Ltd.
Priority to JP2008553053A priority Critical patent/JP5252498B2/en
Priority to MX2009006814A priority patent/MX2009006814A/en
Publication of WO2008084671A1 publication Critical patent/WO2008084671A1/en

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79Acids; Esters
    • C07D213/803Processes of preparation
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/79Acids; Esters
    • C07D213/80Acids; Esters in position 3
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D213/78Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81Amides; Imides
    • C07D213/82Amides; Imides in position 3
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D221/00Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00
    • C07D221/02Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
    • C07D221/04Ortho- or peri-condensed ring systems
    • C07D221/06Ring systems of three rings
    • C07D221/16Ring systems of three rings containing carbocyclic rings other than six-membered
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D227/00Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00
    • C07D227/02Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D227/06Heterocyclic compounds containing rings having one nitrogen atom as the only ring hetero atom, according to more than one of groups C07D203/00 - C07D225/00 with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D227/08Oxygen atoms
    • C07D227/087One doubly-bound oxygen atom in position 2, e.g. lactams
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D405/00Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)

Abstract

Disclosed are: a process for producing a 1-substituted-2-pyridone-3-carboxylic acid derivative which is an important intermediate for the production of a 2-pyridone-3-carbamoyl derivative that has a cannabinoid receptor agonist activity in a simple manner; and a process for producing the 2-pyridone-3-carbamoyl derivative in a simple manner. Specifically disclosed is a process for producing a compound represented by the general formula (II), which comprises: a step A for hydrolyzing a compound represented by the general formula (I); and a step (B) for adding an alcohol to the hydrolysate of the compound represented by the general formula (I) produced in the step A to produce a crystal of the compound represented by the general formula (II). (I) wherein R1 represents an alkyl which may be substituted by a non-reactive substituent, or the like; R2 and R3 independently represent an alkyl or the like, or R2 and R3, together with a carbon atom adjacent to R2 and R3, may form a cycloalkene; R4 represents a hydrogen atom or the like; and R5 represents an alkyl. (II) wherein R1, R2, R3 and R4 are as defined above.
PCT/JP2007/074791 2006-12-27 2007-12-25 Process for producing 1-substituted-2-pyridone-3-carboxylic acid derivative WO2008084671A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2008553053A JP5252498B2 (en) 2006-12-27 2007-12-25 Method for producing 1-substituted-2-pyridone-3-carboxylic acid derivative
MX2009006814A MX2009006814A (en) 2006-12-27 2007-12-25 Process for producing 1-substituted-2-pyridone-3-carboxylic acid derivative.

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2006-351281 2006-12-27
JP2006351281 2006-12-27

Publications (1)

Publication Number Publication Date
WO2008084671A1 true WO2008084671A1 (en) 2008-07-17

Family

ID=39608567

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2007/074791 WO2008084671A1 (en) 2006-12-27 2007-12-25 Process for producing 1-substituted-2-pyridone-3-carboxylic acid derivative

Country Status (5)

Country Link
JP (1) JP5252498B2 (en)
CN (1) CN101668744A (en)
MX (1) MX2009006814A (en)
TW (1) TWI414524B (en)
WO (1) WO2008084671A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130252957A1 (en) * 2009-04-27 2013-09-26 Elan Pharmaceuticals, Inc. Pyridinone antagonists of alpha-4 integrins

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002053543A1 (en) * 2000-12-28 2002-07-11 Shionogi & Co., Ltd. Pyridone derivative having affinity for cannabinoid 2-type receptor
WO2005073222A1 (en) * 2004-01-29 2005-08-11 Pfizer Japan, Inc. 1-isopropyl-2-oxo-1,2-dihydropyridine-3-carboxamide derivatives having 5-ht4 receptor agonistic activity
WO2006046778A1 (en) * 2004-10-28 2006-05-04 Shionogi & Co., Ltd. 3-carbamoyl-2-pyridone derivative

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2002053543A1 (en) * 2000-12-28 2002-07-11 Shionogi & Co., Ltd. Pyridone derivative having affinity for cannabinoid 2-type receptor
WO2005073222A1 (en) * 2004-01-29 2005-08-11 Pfizer Japan, Inc. 1-isopropyl-2-oxo-1,2-dihydropyridine-3-carboxamide derivatives having 5-ht4 receptor agonistic activity
WO2006046778A1 (en) * 2004-10-28 2006-05-04 Shionogi & Co., Ltd. 3-carbamoyl-2-pyridone derivative

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20130252957A1 (en) * 2009-04-27 2013-09-26 Elan Pharmaceuticals, Inc. Pyridinone antagonists of alpha-4 integrins

Also Published As

Publication number Publication date
JPWO2008084671A1 (en) 2010-04-30
JP5252498B2 (en) 2013-07-31
CN101668744A (en) 2010-03-10
TWI414524B (en) 2013-11-11
TW200835692A (en) 2008-09-01
MX2009006814A (en) 2009-07-02

Similar Documents

Publication Publication Date Title
NZ600119A (en) Process and intermediates for the preparation of 5-biphenyl-4-yl-2-methylpentanoic acid derivatives
MX2009001816A (en) Method for the production of d,l-2-hydroxy-4-alkylthio butyric acid.
WO2009151256A3 (en) Method for preparing clopidogrel and its derivatives
TW200745076A (en) Process for production of methylene disulfonate compound
DK1877384T3 (en) Process for preparing optionally 2-substituted 1,6-dihydro-6-oxo-4-pyrimidinecarboxylic acids
MX2009012602A (en) Process for the production of pyrazoles.
PL1920046T3 (en) Method of ethanol production by aid of liquid yeast
MY150280A (en) Process of preparing derivatives of 1-(2-halobiphenyl-4-yl)-cyclopropanecarboxylic acid
IL177431A0 (en) New process for the synthesis of substituted alpha-aminoindan derivatives
DK2019114T3 (en) Method of Preparation of Drospirenone
WO2009066735A1 (en) Method for producing 2-azaadamantane
IN2012DN01815A (en)
WO2009028676A1 (en) Method for producing carbonyl compound an pro-oxidant used for production of carbonyl compound
TW201129535A (en) Alcoholic hydroxyl-containing compounds and making method
WO2007049295A3 (en) An improved one pot process for making key intermediate for gemcitabine hcl
UA89218C2 (en) Process for the preparation of intermediates (variants)
MX2011008348A (en) Process for producing phenyl-substituted heterocyclic derivative through coupling using transition metal catalyst.
WO2014003203A3 (en) Method for producing stereoselective epoxyketone compound
TW200619201A (en) Process for the preparation of pyrazoles
UA99455C2 (en) Epoxy compound, process for the preparation thereof and process for the preparation of oxazole compound
UA90940C2 (en) Process for the production of 5-alkoxy-4-hydroxymethylpyrazole compound
WO2008084671A1 (en) Process for producing 1-substituted-2-pyridone-3-carboxylic acid derivative
WO2006034812A3 (en) Method for producing an optically active 2-methyl-alkane-1-ol from the corresponding 2-methylalk-2-en-1-al, comprising carbonyl-selective reduction, enantioselective hydration and lipase-catalyzed, stereoselective acylation in order to enrich the desired enantiomer
NZ592864A (en) Processes for the preparation of cyclopropyl-amide derivatives
TW200740763A (en) A method for preparing 5-hydroxy-1-alkyl pyrazole derivatives

Legal Events

Date Code Title Description
WWE Wipo information: entry into national phase

Ref document number: 200780051801.9

Country of ref document: CN

121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 07860020

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2008553053

Country of ref document: JP

WWE Wipo information: entry into national phase

Ref document number: MX/A/2009/006814

Country of ref document: MX

WWE Wipo information: entry into national phase

Ref document number: 3720/CHENP/2009

Country of ref document: IN

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 07860020

Country of ref document: EP

Kind code of ref document: A1