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WO1999033807A3 - Synthesis of pharmaceutically useful pyridine derivatives (intermediates) employing free radical substitution reactions to functionalize the 2-position of the pyridine - Google Patents

Synthesis of pharmaceutically useful pyridine derivatives (intermediates) employing free radical substitution reactions to functionalize the 2-position of the pyridine Download PDF

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Publication number
WO1999033807A3
WO1999033807A3 PCT/CA1998/001153 CA9801153W WO9933807A3 WO 1999033807 A3 WO1999033807 A3 WO 1999033807A3 CA 9801153 W CA9801153 W CA 9801153W WO 9933807 A3 WO9933807 A3 WO 9933807A3
Authority
WO
WIPO (PCT)
Prior art keywords
pyridine
functionalize
free radical
intermediates
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/CA1998/001153
Other languages
French (fr)
Other versions
WO1999033807A2 (en
Inventor
Michel Zoghbi
Liquin Chen
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.)
PDI Research Laboratories Inc
Original Assignee
PDI Research Laboratories 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
Priority claimed from CA 2225863 external-priority patent/CA2225863A1/en
Application filed by PDI Research Laboratories Inc filed Critical PDI Research Laboratories Inc
Priority to US09/582,345 priority Critical patent/US6437139B1/en
Priority to AU16566/99A priority patent/AU1656699A/en
Publication of WO1999033807A2 publication Critical patent/WO1999033807A2/en
Publication of WO1999033807A3 publication Critical patent/WO1999033807A3/en
Anticipated expiration legal-status Critical
Ceased 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
    • C07D213/60—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 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/68—One oxygen atom attached in position 4

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)

Abstract

A process is provided for the preparation of compounds of formula (I) useful in the preparation of compounds such as Omeprazole, Lansoprazole and Pantoprazole, wherein R1=H or CH¿3, R?2=H or CH¿3, R?3=Alkoxy (1-4C), OCH¿2?CF3, Cyano, Hydrogen, Halogen, Acetoxy or Aryloxy, any electron withdrawing group or salts (organic or inorganic) of electron donating groups, R=Alkoxy, Hydroxy, Halogen, Activated ester, Tosylate, Mesylate, Thiol or Xanthyl, wherein the process for the preparation of compound of formula (I) employs a free radical reaction to functionalize the 2-position.
PCT/CA1998/001153 1997-05-06 1998-12-11 Synthesis of pharmaceutically useful pyridine derivatives (intermediates) employing free radical substitution reactions to functionalize the 2-position of the pyridine Ceased WO1999033807A2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US09/582,345 US6437139B1 (en) 1997-05-06 1998-12-11 Synthesis of pharmaceutically useful pyridine derivatives
AU16566/99A AU1656699A (en) 1997-12-24 1998-12-11 Synthesis of pharmaceutically useful pyridine derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CA 2225863 CA2225863A1 (en) 1997-05-06 1997-12-24 Synthesis of pharmaceutical useful pyridine derivatives
CA2,225,863 1997-12-24

Publications (2)

Publication Number Publication Date
WO1999033807A2 WO1999033807A2 (en) 1999-07-08
WO1999033807A3 true WO1999033807A3 (en) 1999-10-21

Family

ID=4161949

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/CA1998/001153 Ceased WO1999033807A2 (en) 1997-05-06 1998-12-11 Synthesis of pharmaceutically useful pyridine derivatives (intermediates) employing free radical substitution reactions to functionalize the 2-position of the pyridine

Country Status (2)

Country Link
AU (1) AU1656699A (en)
WO (1) WO1999033807A2 (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105153024A (en) * 2015-10-10 2015-12-16 成都同创源医药科技有限公司 Synthetic method of 3,4-substituted 2-picolinic acid
CN105153023B (en) * 2015-10-10 2018-04-13 成都同创源医药科技有限公司 The synthetic method of 2 amino, 4 bromopyridine
CN113797968B (en) * 2021-08-19 2022-08-05 万华化学集团股份有限公司 Preparation of 2-chloroisonicotinic acid-phosphomolybdic acid catalyst and preparation method of polyglycerol fatty acid ester

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD29611A (en) *
SU330737A1 (en) * 1970-03-20 1973-05-22 METHOD OF JOINT PREPARATION OF 2,3-DICHLOR-, 2,3,6-TRICHLOR-2, 3, 4, 5-TETRACHLOR- AND PENTAL CHRORINE
EP0103553A1 (en) * 1982-08-26 1984-03-21 Aktiebolaget Hässle Intermediates for the preparation of omeprazole
EP0172595A1 (en) * 1984-08-20 1986-02-26 SOLVAY & Cie (Société Anonyme) Process for the preparation of chlorinated derivatives of pyridine, and radical initiators used in this process
EP0357103A1 (en) * 1988-07-15 1990-03-07 Solvay Process for the preparation of 2,6-dichloropyridine and the use of bis(trichloromethyl)sulphone in this process
KR910009817A (en) * 1989-11-02 1991-06-28 에드먼드 에이 콜린즈 Impact polyacetal resin composition exhibiting excellent antistatic properties
EP0533131A1 (en) * 1991-09-19 1993-03-24 Hoechst Aktiengesellschaft Process for selectively mono-ortho-hydroxy alkylation of 4-substituted pyridine derivatives
WO1998050361A2 (en) * 1997-05-06 1998-11-12 Pdi-Research Laboratories, Inc. Synthesis of pharmaceutically useful pyridine derivatives

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DD29611A (en) *
SU330737A1 (en) * 1970-03-20 1973-05-22 METHOD OF JOINT PREPARATION OF 2,3-DICHLOR-, 2,3,6-TRICHLOR-2, 3, 4, 5-TETRACHLOR- AND PENTAL CHRORINE
EP0103553A1 (en) * 1982-08-26 1984-03-21 Aktiebolaget Hässle Intermediates for the preparation of omeprazole
EP0172595A1 (en) * 1984-08-20 1986-02-26 SOLVAY & Cie (Société Anonyme) Process for the preparation of chlorinated derivatives of pyridine, and radical initiators used in this process
EP0357103A1 (en) * 1988-07-15 1990-03-07 Solvay Process for the preparation of 2,6-dichloropyridine and the use of bis(trichloromethyl)sulphone in this process
KR910009817A (en) * 1989-11-02 1991-06-28 에드먼드 에이 콜린즈 Impact polyacetal resin composition exhibiting excellent antistatic properties
EP0533131A1 (en) * 1991-09-19 1993-03-24 Hoechst Aktiengesellschaft Process for selectively mono-ortho-hydroxy alkylation of 4-substituted pyridine derivatives
WO1998050361A2 (en) * 1997-05-06 1998-11-12 Pdi-Research Laboratories, Inc. Synthesis of pharmaceutically useful pyridine derivatives

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
BERNARDI R ET AL: "NUCLEOPHILIC CHARACTER OF CARBON FREE RADICALS. A NEW CONVENIENT, SELECTIVE CARBOXYLATION OF HETEROAROMATIC BASES", TETRAHEDRON LETTERS, no. 9, 1973, pages 645 - 648, XP002073298 *
CHOU S -Y ET AL: "SYNTHESIS OF 2-HYDROXYMETHYL-3,5-DIMETHYL-4-METHOXYPYRIDINE: A KEY INTERMEDIATE FOR OMEPRAZOLE", HETEROCYCLES, vol. 45, no. 1, 1997, pages 77 - 85, XP002073301 *
CITTERIO A ET AL: "NUCLEOPHILIC CHARACTER OF THE ALKYL RADICALS. 19. ABSOLUTE RATE CONSTANTS IN THE HOMOLYTIC ALKYLATION OF PROTONATED HETEROAROMATIC BASES BY N-BUTYL AND TERT-BUTYL RADICALS", JOURNAL OF ORGANIC CHEMISTRY, vol. 45, 1980, pages 4752 - 4757, XP002073300 *
DATABASE WPI Section Ch Week 674, Derwent World Patents Index; Class C02, AN 74-10791v, XP002073303 *
DATABASE WPI Section Ch Week 9250, Derwent World Patents Index; Class B03, AN 92-412945, XP002073302 *
FONTANA F ET AL: "HOMOLYTIC ACYLATIONS OF PROTONATED PYRIDINES AND PYRAZINES WITH ALPHA-KETO ACIDS: THE PROBLEM OF MONOACYLATION", JOURNAL OF ORGANIC CHEMISTRY, vol. 56, 1991, pages 2866 - 2869, XP002073299 *
MINISCI F: "NOVEL APPLICATIONS OF FREE-RADICAL REACTIONS IN PREPARATIVE ORGANIC CHEMISTRY", SYNTHESIS, no. 1, 1973, pages 1 - 24, XP002073297 *
MINISCI,F. ET AL.: "Advances in Homolytic Substitution of Heteroaromatic Compounds", ADV.HETEROCYCL.CHEM., vol. 16, 1974, NEW YORK, pages 123 - 180, XP002101509 *

Also Published As

Publication number Publication date
WO1999033807A2 (en) 1999-07-08
AU1656699A (en) 1999-07-19

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