CA2675142C - Fused aromatic difluoromethanephosphonates as protein tyrosine phosphatase 1b (ptp-1b) inhibitors - Google Patents

Fused aromatic difluoromethanephosphonates as protein tyrosine phosphatase 1b (ptp-1b) inhibitors Download PDF

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Publication number
CA2675142C
CA2675142C CA2675142A CA2675142A CA2675142C CA 2675142 C CA2675142 C CA 2675142C CA 2675142 A CA2675142 A CA 2675142A CA 2675142 A CA2675142 A CA 2675142A CA 2675142 C CA2675142 C CA 2675142C
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CA
Canada
Prior art keywords
inhibitors
optionally substituted
compound
pharmaceutically acceptable
agonists
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.)
Expired - Fee Related
Application number
CA2675142A
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English (en)
French (fr)
Other versions
CA2675142A1 (en
Inventor
John Colucci
Marie-Claire Wilson
Yongxin Han
Claude Dufresne
Michel Belley
Cheuk K. Lau
Christopher Bayly
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Kaneq Pharma Inc
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Kaneq Pharma Inc
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Publication of CA2675142A1 publication Critical patent/CA2675142A1/en
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Publication of CA2675142C publication Critical patent/CA2675142C/en
Expired - Fee Related legal-status Critical Current
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/576—Six-membered rings
    • C07F9/60—Quinoline or hydrogenated quinoline ring systems
    • 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
    • A61K31/66—Phosphorus compounds
    • A61K31/662—Phosphorus acids or esters thereof having P—C bonds, e.g. foscarnet, trichlorfon
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • 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]
    • 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
    • A61P3/04—Anorexiants; Antiobesity agents
    • 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
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
    • C07F9/3834—Aromatic acids (P-C aromatic linkage)
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Diabetes (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Oncology (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Child & Adolescent Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
CA2675142A 2007-01-26 2008-01-24 Fused aromatic difluoromethanephosphonates as protein tyrosine phosphatase 1b (ptp-1b) inhibitors Expired - Fee Related CA2675142C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US89770007P 2007-01-26 2007-01-26
US60/897,700 2007-01-26
PCT/CA2008/000172 WO2008089581A1 (en) 2007-01-26 2008-01-24 Fused aromatic ptp-1b inhibitors

Publications (2)

Publication Number Publication Date
CA2675142A1 CA2675142A1 (en) 2008-07-31
CA2675142C true CA2675142C (en) 2014-08-19

Family

ID=39644072

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2675142A Expired - Fee Related CA2675142C (en) 2007-01-26 2008-01-24 Fused aromatic difluoromethanephosphonates as protein tyrosine phosphatase 1b (ptp-1b) inhibitors

Country Status (16)

Country Link
US (4) US8168815B2 (enExample)
EP (1) EP2114971B1 (enExample)
JP (1) JP5570223B2 (enExample)
KR (1) KR101568799B1 (enExample)
CN (1) CN102317296B (enExample)
AU (1) AU2008209296B2 (enExample)
BR (1) BRPI0806789B8 (enExample)
CA (1) CA2675142C (enExample)
DK (1) DK2114971T3 (enExample)
ES (1) ES2547386T3 (enExample)
IL (1) IL199742A (enExample)
MX (1) MX2009007911A (enExample)
NZ (2) NZ600947A (enExample)
RU (1) RU2462469C2 (enExample)
WO (1) WO2008089581A1 (enExample)
ZA (1) ZA200904679B (enExample)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008089581A1 (en) * 2007-01-26 2008-07-31 Merck Frosst Canada Ltd. Fused aromatic ptp-1b inhibitors
WO2011107494A1 (de) 2010-03-03 2011-09-09 Sanofi Neue aromatische glykosidderivate, diese verbindungen enthaltende arzneimittel und deren verwendung
EP2582709B1 (de) 2010-06-18 2018-01-24 Sanofi Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen
US8530413B2 (en) 2010-06-21 2013-09-10 Sanofi Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments
TW201215388A (en) 2010-07-05 2012-04-16 Sanofi Sa (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments
TW201221505A (en) 2010-07-05 2012-06-01 Sanofi Sa Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament
TW201215387A (en) 2010-07-05 2012-04-16 Sanofi Aventis Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament
WO2013037390A1 (en) 2011-09-12 2013-03-21 Sanofi 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors
WO2013045413A1 (en) 2011-09-27 2013-04-04 Sanofi 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors
CA2870488A1 (en) * 2012-04-16 2013-10-24 Kaneq Pharma Inc. Fused aromatic phosphonate derivatives as precursors to ptp-1b inhibitors
WO2014141110A2 (en) * 2013-03-14 2014-09-18 Curadev Pharma Pvt. Ltd. Aminonitriles as kynurenine pathway inhibitors
WO2015127548A1 (en) 2014-02-28 2015-09-03 The Royal Institution For The Advancement Of Learning / Mcgill University Tc-ptp inhibitors as apc activators for immunotherapy
CN108159069A (zh) * 2018-01-26 2018-06-15 广东省微生物研究所（广东省微生物分析检测中心） 灰树花多糖f2在制备治疗高脂血症药物、预防或延缓动脉粥样硬化药物中的应用
WO2023220833A1 (en) * 2022-05-19 2023-11-23 Kanyr Pharma Inc. Combined inhibition of tyrosine phosphatases tcptp and ptp1b and pd-1 blockage immunotherapy in the treatment of cancer
WO2024123585A1 (en) * 2022-12-05 2024-06-13 Merck Sharp & Dohme Llc Substituted quinazoline derivatives and methods of use thereof

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FI83421C (fi) * 1989-06-21 1991-07-10 Huhtamaeki Oy Foerfarande foer framstaellning av farmakologiskt anvaendbara metylenbisfosfonsyraderivat.
WO1997028149A1 (en) 1996-02-02 1997-08-07 Merck & Co., Inc. Method for raising hdl cholesterol levels
US6174874B1 (en) * 1998-09-21 2001-01-16 Merck Frosst Canada & Co. Phosphonic acids derivatives as inhibitors of protein tyrosine phosphate 1B (PTP-1B)
JP2003518130A (ja) * 1999-12-22 2003-06-03 メルク フロスト カナダ アンド カンパニー 蛋白チロシンホスファターゼ１ｂ（ｐｔｐ−１ｂ）阻害薬としてのホスホン酸誘導体
CA2402414A1 (en) * 2000-03-22 2001-09-27 Christopher Bayly Sulfur substituted aryldifluoromethylphosphonic acids as ptp-1b inhibitors
AU7705601A (en) 2000-07-25 2002-02-05 Merck & Co Inc N-substituted indoles useful in the treatment of diabetes
CA2495943C (en) 2002-08-29 2009-07-21 Merck & Co., Inc. Indoles having anti-diabetic activity
UA84050C2 (en) * 2004-01-30 2008-09-10 Медивир Аб Hcv ns-3-serine protease inhibitors
JP4922924B2 (ja) 2004-04-13 2012-04-25 メルク・シャープ・エンド・ドーム・コーポレイション Ｃｅｔｐ阻害薬
DOP2005000123A (es) 2004-07-02 2011-07-15 Merck Sharp & Dohme Inhibidores de cetp
WO2006055525A2 (en) 2004-11-15 2006-05-26 Ceptyr, Inc. Protein tyrosine phosphatase inhibitors and methods of use thereof
WO2008089581A1 (en) * 2007-01-26 2008-07-31 Merck Frosst Canada Ltd. Fused aromatic ptp-1b inhibitors

Also Published As

Publication number Publication date
NZ600947A (en) 2012-12-21
AU2008209296B2 (en) 2012-12-20
JP2010516715A (ja) 2010-05-20
CN102317296B (zh) 2015-05-27
HK1165806A1 (en) 2012-10-12
US8481742B2 (en) 2013-07-09
CN102317296A (zh) 2012-01-11
US20120178679A1 (en) 2012-07-12
US8927526B2 (en) 2015-01-06
WO2008089581A1 (en) 2008-07-31
EP2114971B1 (en) 2015-06-17
RU2462469C2 (ru) 2012-09-27
DK2114971T3 (en) 2015-08-31
ZA200904679B (en) 2010-04-28
EP2114971A4 (en) 2011-07-06
JP5570223B2 (ja) 2014-08-13
EP2114971A1 (en) 2009-11-11
RU2009132092A (ru) 2011-03-10
AU2008209296A1 (en) 2008-07-31
BRPI0806789B1 (pt) 2020-01-28
IL199742A (en) 2014-03-31
BRPI0806789A2 (pt) 2011-09-13
IL199742A0 (en) 2010-04-15
KR101568799B1 (ko) 2015-11-12
US20150045325A1 (en) 2015-02-12
US20130281365A1 (en) 2013-10-24
US9334295B2 (en) 2016-05-10
KR20090108102A (ko) 2009-10-14
MX2009007911A (es) 2009-07-31
NZ578296A (en) 2012-07-27
US8168815B2 (en) 2012-05-01
CA2675142A1 (en) 2008-07-31
ES2547386T3 (es) 2015-10-05
BRPI0806789B8 (pt) 2021-05-25
US20100022477A1 (en) 2010-01-28

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