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WO2010005520A3 - Deuterated ibudilast - Google Patents

Deuterated ibudilast Download PDF

Info

Publication number
WO2010005520A3
WO2010005520A3 PCT/US2009/003888 US2009003888W WO2010005520A3 WO 2010005520 A3 WO2010005520 A3 WO 2010005520A3 US 2009003888 W US2009003888 W US 2009003888W WO 2010005520 A3 WO2010005520 A3 WO 2010005520A3
Authority
WO
WIPO (PCT)
Prior art keywords
ibudilast
acylpyrazolo
inhibitor
derivatives
alkyl
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/US2009/003888
Other languages
French (fr)
Other versions
WO2010005520A2 (en
Inventor
Julie F. Liu
Rose A. Persichetti
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.)
Concert Pharmaceuticals Inc
Original Assignee
Concert Pharmaceuticals 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
Application filed by Concert Pharmaceuticals Inc filed Critical Concert Pharmaceuticals Inc
Publication of WO2010005520A2 publication Critical patent/WO2010005520A2/en
Publication of WO2010005520A3 publication Critical patent/WO2010005520A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pulmonology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

This invention relates to novel compounds that are 2-alkyl-3-acylpyrazolo[l,5- a]pyridines, their derivatives, and pharmaceutically acceptable salts thereof. More specifically, the invention relates to 2-alkyl-3-acylpyrazolo[l,5-a]pyridine compounds that are derivatives of ibudilast. This invention also provides compositions comprising a compound of this invention and the use of such compositions in methods of treating diseases and conditions that are beneficially treated by administering a phosphodiesterase (PDE) inhibitor, a leukotriene CysLTl (LTD4) antagonist, an inhibitor of nitric oxide synthase, and/or a glial cell activation suppressant, such as ibudilast.
PCT/US2009/003888 2008-06-30 2009-06-30 2-alkyl-3-acylpyrazolo[1,5-a]pyridine derivatives Ceased WO2010005520A2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US13352308P 2008-06-30 2008-06-30
US61/133,523 2008-06-30

Publications (2)

Publication Number Publication Date
WO2010005520A2 WO2010005520A2 (en) 2010-01-14
WO2010005520A3 true WO2010005520A3 (en) 2010-03-04

Family

ID=41056848

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2009/003888 Ceased WO2010005520A2 (en) 2008-06-30 2009-06-30 2-alkyl-3-acylpyrazolo[1,5-a]pyridine derivatives

Country Status (1)

Country Link
WO (1) WO2010005520A2 (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3850941A (en) * 1972-03-30 1974-11-26 Kyorin Seiyaku Kk 2-alkyl-3-acylpyrazolo(1,5-a)pyridines
WO1995026325A2 (en) * 1994-03-25 1995-10-05 Isotechnika Inc. Enhancement of the efficacy of drugs by deuteration
EP1570847A1 (en) * 2002-12-03 2005-09-07 Kyorin Pharmaceutical Co., Ltd. Phosphodiesterase 10a inhibitors

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3850941A (en) * 1972-03-30 1974-11-26 Kyorin Seiyaku Kk 2-alkyl-3-acylpyrazolo(1,5-a)pyridines
WO1995026325A2 (en) * 1994-03-25 1995-10-05 Isotechnika Inc. Enhancement of the efficacy of drugs by deuteration
EP1570847A1 (en) * 2002-12-03 2005-09-07 Kyorin Pharmaceutical Co., Ltd. Phosphodiesterase 10a inhibitors

Non-Patent Citations (11)

* Cited by examiner, † Cited by third party
Title
ATARASHII GANKA , 15(4), 573-578 CODEN: ATGAEX; ISSN: 0910-1810, 1998, XP001539556 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; KOMURO ET AL.: "Disposition of 0.01% ibudilast ophthalmic solution. IV. Distribution, metabolism, and excretion after a single instillation of 14C-labeled ibudilast in albino rabbits", XP002546078, retrieved from STN Database accession no. 1998:298386 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; NAGATSU; TAKAGI: "Synthesis of carbon-14 and deuterium labeled 3-isobutyryl-2-isopropylpyrazolo[1,5-a]pyridine", XP002546080, retrieved from STN Database accession no. 1986:207196 *
DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; TAKAGI; ENDO: "Studies on the metabolic fate of 3-isobutyryl-2-isopropylpyrazolo[1,5-a]pyridine (KC-404). (2). Metabolism in rats, dogs and monkeys", XP002546079, retrieved from STN Database accession no. 1986:141683 *
FOSTER: "Deuterium isotope effects in the metabolism of drugs and xenobiotics: implications for drug design", ADVANCES IN DRUG RESEARCH, vol. 14, 1 January 1985 (1985-01-01), pages 1 - 40, XP009086953, ISSN: 0065-2490 *
JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS , 22(7), 735-43 CODEN: JLCRD4; ISSN: 0362-4803, 1985 *
LEDEBOER ET AL.: "Ibudilast (AV-411). A new class therapeutic candidate for neuropathic pain and opioid withdrawal syndromes", EXPERT OPINION ON INVESTIGATIONAL DRUGS, ASHLEY PUBLICATIONS LTD., LONDON, GB, vol. 16, no. 7, 1 July 2007 (2007-07-01), pages 935 - 950, XP002483491, ISSN: 1354-3784 *
O'NEIL ET AL. (EDS.): "The Merck Index, 13th ed.", 2001, MERCK & CO., INC., WHITEHOUSE STATION, NJ, XP002546076 *
OYO YAKURI, vol. 30, no. 6, 1985, pages 983 - 994, XP009122761 *
SYNFINE RESEARCH INC.: "Online Catalogue: Ibudilast-d7", 2009, SYNFINE RESEARCH INC., RICHMOND HILL (ONTARIO, CANADA), XP002546077 *
YARNELL: "Heavy-Hydrogen Drugs Turn Heads, Again", CHEMICAL & ENGINEERING NEWS, vol. 87, no. 25, 22 June 2009 (2009-06-22), pages 36 - 39, XP002546075, Retrieved from the Internet <URL:http://pubs.acs.org/cen/science/87/8725sci1.html> [retrieved on 20090916] *

Also Published As

Publication number Publication date
WO2010005520A2 (en) 2010-01-14

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