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CA2485739A1 - Process for preparing 1-(6-methylpyridin-3-yl)-2-[(4-(methylsulphonyl)phenyl]ethanone - Google Patents

Process for preparing 1-(6-methylpyridin-3-yl)-2-[(4-(methylsulphonyl)phenyl]ethanone

Info

Publication number
CA2485739A1
CA2485739A1 CA002485739A CA2485739A CA2485739A1 CA 2485739 A1 CA2485739 A1 CA 2485739A1 CA 002485739 A CA002485739 A CA 002485739A CA 2485739 A CA2485739 A CA 2485739A CA 2485739 A1 CA2485739 A1 CA 2485739A1
Authority
CA
Canada
Prior art keywords
methylpyridin
ethanone
phenyl
preparing
methylsulphonyl
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.)
Granted
Application number
CA002485739A
Other languages
French (fr)
Other versions
CA2485739C (en
Inventor
Erich Armbruster
Yves Bessard
David Kuo
Ralf Proplesch
Jean-Paul Roduit
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.)
Lonza AG
Merck and Co Inc
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of CA2485739A1 publication Critical patent/CA2485739A1/en
Application granted granted Critical
Publication of CA2485739C publication Critical patent/CA2485739C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic 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
    • C07D213/02—Heterocyclic 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
    • C07D213/04—Heterocyclic 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
    • C07D213/24—Heterocyclic 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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/57—Nitriles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic 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
    • C07D213/02—Heterocyclic 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
    • C07D213/04—Heterocyclic 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
    • C07D213/24—Heterocyclic 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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pain & Pain Management (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Rheumatology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pyridine Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

1- (6-Methylpyridin-3-yl) -2- [ (4- (methylsulfonyl)phenyl] ethanone of the formula <See formula I> and a process for preparing such is disclosed. 1-(6-Methylpyridin-3-yl) -2- [(4-(methylsulfonyl)phenyl] ethanone is an important intermediate for preparing so-called COX-2 inhibitors, which are pharmaceutically active compounds having analgesic and anti-inflammatory action.
CA002485739A 1999-01-14 2000-01-13 Process for preparing 1-(6-methylpyridin-3-yl)-2-[(4-(methylsulphonyl)phenyl]ethanone Expired - Fee Related CA2485739C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
CH99100590.1 1999-01-14
EP99100590 1999-01-14
US14599699P 1999-07-29 1999-07-29
US60/145,996 1999-07-29
CA002359958A CA2359958C (en) 1999-01-14 2000-01-13 Process for preparing 1-(6-methylpyridin-3yl)-2-[(4-methylsulfonyl)phenyl]ethanone

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CA002359958A Division CA2359958C (en) 1999-01-14 2000-01-13 Process for preparing 1-(6-methylpyridin-3yl)-2-[(4-methylsulfonyl)phenyl]ethanone

Publications (2)

Publication Number Publication Date
CA2485739A1 true CA2485739A1 (en) 2000-07-20
CA2485739C CA2485739C (en) 2009-09-22

Family

ID=34089809

Family Applications (2)

Application Number Title Priority Date Filing Date
CA002359958A Expired - Fee Related CA2359958C (en) 1999-01-14 2000-01-13 Process for preparing 1-(6-methylpyridin-3yl)-2-[(4-methylsulfonyl)phenyl]ethanone
CA002485739A Expired - Fee Related CA2485739C (en) 1999-01-14 2000-01-13 Process for preparing 1-(6-methylpyridin-3-yl)-2-[(4-(methylsulphonyl)phenyl]ethanone

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CA002359958A Expired - Fee Related CA2359958C (en) 1999-01-14 2000-01-13 Process for preparing 1-(6-methylpyridin-3yl)-2-[(4-methylsulfonyl)phenyl]ethanone

Country Status (15)

Country Link
EP (2) EP1394149B1 (en)
JP (1) JP4765167B2 (en)
CN (2) CN1170820C (en)
AT (2) ATE253559T1 (en)
AU (1) AU2290800A (en)
CA (2) CA2359958C (en)
CZ (1) CZ302270B6 (en)
DE (2) DE50009312D1 (en)
DK (2) DK1159270T3 (en)
ES (2) ES2235138T3 (en)
HU (1) HUP0105124A3 (en)
IL (1) IL143981A0 (en)
PT (2) PT1159270E (en)
SK (1) SK284903B6 (en)
WO (1) WO2000042014A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104725300A (en) * 2015-02-28 2015-06-24 宁波九胜创新医药科技有限公司 Preparation method of 1-(6-methyl pyridine-3-yl)-2-(4-methylsulfonyl phenyl) ethanone

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3313683A (en) * 1963-04-22 1967-04-11 Lilly Co Eli Nematocidal and fungicidal methods
FR2074674A1 (en) * 1970-01-16 1971-10-08 Simafex Sulphonamide/aldehyde-bisulphite complexes - antibacterials with very high solubility in water
US4155909A (en) * 1977-06-13 1979-05-22 Philip Morris Incorporated 2-Alkyl nicotinoids and processes for their production
US5596008A (en) * 1995-02-10 1997-01-21 G. D. Searle & Co. 3,4-Diaryl substituted pyridines for the treatment of inflammation
DK0912518T3 (en) * 1996-07-18 2003-12-08 Merck Frosst Canada Inc Substituted pyridines as selective cyclooxygenase-2 inhibitors
TW492959B (en) * 1997-04-18 2002-07-01 Merck & Co Inc Process for making 2-aryl-3-aryl-5-halo pyridines useful as cox-2 inhibitors
AR015938A1 (en) * 1997-09-25 2001-05-30 Merck Sharp & Dohme PROCEDURE TO PREPARE DIARIL PIRIDINES USEFUL AS COX-2 INHIBITORS AND INTERMEDIATE COMPOUND
CA2329193C (en) * 1998-04-24 2007-01-23 Merck & Co., Inc. Process for synthesizing cox-2 inhibitors

Also Published As

Publication number Publication date
CA2359958A1 (en) 2000-07-20
CZ302270B6 (en) 2011-01-19
CA2359958C (en) 2006-04-04
DE50009312D1 (en) 2005-02-24
CN1281589C (en) 2006-10-25
CN1359374A (en) 2002-07-17
DE50004327D1 (en) 2003-12-11
EP1394149B1 (en) 2005-01-19
CA2485739C (en) 2009-09-22
WO2000042014A2 (en) 2000-07-20
ES2209807T3 (en) 2004-07-01
WO2000042014A3 (en) 2000-12-07
PT1394149E (en) 2005-05-31
SK284903B6 (en) 2006-02-02
ES2235138T3 (en) 2005-07-01
EP1159270B1 (en) 2003-11-05
CZ20012457A3 (en) 2002-01-16
SK9722001A3 (en) 2001-12-03
CN1583723A (en) 2005-02-23
EP1159270A2 (en) 2001-12-05
ATE253559T1 (en) 2003-11-15
HUP0105124A2 (en) 2002-04-29
ATE287396T1 (en) 2005-02-15
DK1159270T3 (en) 2004-02-23
EP1394149A1 (en) 2004-03-03
HUP0105124A3 (en) 2002-05-28
IL143981A0 (en) 2002-04-21
DK1394149T3 (en) 2005-04-04
AU2290800A (en) 2000-08-01
JP4765167B2 (en) 2011-09-07
PT1159270E (en) 2004-03-31
JP2003518002A (en) 2003-06-03
CN1170820C (en) 2004-10-13

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Legal Events

Date Code Title Description
EEER Examination request
FZDC Discontinued application reinstated
MKLA Lapsed

Effective date: 20130114