AU2014229065B2 - Methods of synthesizing a difluorolactam analog - Google Patents

Methods of synthesizing a difluorolactam analog Download PDF

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Publication number
AU2014229065B2
AU2014229065B2 AU2014229065A AU2014229065A AU2014229065B2 AU 2014229065 B2 AU2014229065 B2 AU 2014229065B2 AU 2014229065 A AU2014229065 A AU 2014229065A AU 2014229065 A AU2014229065 A AU 2014229065A AU 2014229065 B2 AU2014229065 B2 AU 2014229065B2
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Australia
Prior art keywords
compound
formula
methyl
mmol
acid
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Ceased
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AU2014229065A
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AU2014229065A1 (en
Inventor
Stephen Douglas Barrett
Joseph Michael Colombo
Bradlee David Germain
Andriy Kornilov
James Bernard Kramer
Adam Uzieblo
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Cayman Chemical Co Inc
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Cayman Chemical Co Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic 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 carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B39/00—Halogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • 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)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Rheumatology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Ophthalmology & Optometry (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Neurosurgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Pyrrole Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
AU2014229065A 2013-03-15 2014-03-14 Methods of synthesizing a difluorolactam analog Ceased AU2014229065B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201361799334P 2013-03-15 2013-03-15
US61/799,334 2013-03-15
PCT/US2014/028933 WO2014144500A2 (en) 2013-03-15 2014-03-14 Methods of synthesizing a difluorolactam analog

Publications (2)

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AU2014229065A1 AU2014229065A1 (en) 2015-09-17
AU2014229065B2 true AU2014229065B2 (en) 2017-03-09

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AU2014229065A Ceased AU2014229065B2 (en) 2013-03-15 2014-03-14 Methods of synthesizing a difluorolactam analog

Country Status (7)

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US (3) US9914725B2 (cg-RX-API-DMAC7.html)
EP (1) EP2970234B1 (cg-RX-API-DMAC7.html)
JP (1) JP6368351B2 (cg-RX-API-DMAC7.html)
AU (1) AU2014229065B2 (cg-RX-API-DMAC7.html)
CA (1) CA2903314C (cg-RX-API-DMAC7.html)
IL (1) IL241042B (cg-RX-API-DMAC7.html)
WO (1) WO2014144500A2 (cg-RX-API-DMAC7.html)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9440919B2 (en) 2012-07-19 2016-09-13 Cayman Chemical Company, Inc. Difluorolactam compositions for EP4-mediated osteo related diseases and conditions
HU231033B1 (hu) 2016-03-22 2019-12-30 CHINOIN Gyógyszer és Vegyészeti Termékek Gyára Zrt. Eljárás 3-as kötést tartalmazó optikailag aktív karbonsavak, karbonsav sók és karbonsav származékok előállítására
CN106699604B (zh) * 2017-01-09 2019-01-01 四川同晟生物医药有限公司 一种沙库比曲及其中间体的制备方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009023193A1 (en) * 2007-08-15 2009-02-19 Cytokinetics, Incorporated Certain chemical entities, compositions, and methods
WO2014015247A1 (en) * 2012-07-19 2014-01-23 Cayman Chemical Company, Inc. Difluorolactam compounds as ep4 receptor-selective agonists for use in the treatment of ep4-mediated disease and conditions

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3975399A (en) 1974-08-06 1976-08-17 E. I. Du Pont De Nemours And Company 1,5-Disubstituted-2-pyrrolidinones, -3-pyrrolin-2-ones, and -4-pyrrolin-2-ones
DE2517771A1 (de) 1975-04-18 1976-10-28 Schering Ag Neue prostaglandin-acetylen-analoga und verfahren zu ihrer herstellung
CA1085859A (en) 1975-06-27 1980-09-16 Wilhelm Bartmann Pyrrolidones and process for their manufacture
DE2528664A1 (de) 1975-06-27 1977-01-13 Hoechst Ag Pyrrolidone und verfahren zu ihrer herstellung
DE2619638A1 (de) 1976-05-04 1977-11-17 Hoechst Ag Pyrrolidone und verfahren zu ihrer herstellung
US4177346A (en) 1976-08-06 1979-12-04 Pfizer Inc. 1,5-Disubstituted-2-pyrrolidones
US4320136A (en) 1980-08-11 1982-03-16 E. I. Du Pont De Nemours And Company 8-Aza-16,16-difluoroprostanoids
US4311644A (en) * 1981-01-30 1982-01-19 E. R. Squibb & Sons, Inc. Method for preparing 10,10-difluoro prostacyclin intermediates and new compounds produced thereby
US4456613A (en) 1982-12-27 1984-06-26 E. I. Du Pont De Nemours And Company 6-Keto- and 6-hydroxy-8-azaprostanoids and anti-ulcer use thereof
NZ525164A (en) 2000-11-27 2005-04-29 Pfizer Prod Inc EP4 receptor selective agonists in the treatment of osteoporosis
AU2002226035A1 (en) * 2000-12-07 2002-06-18 Michael P Doyle Lewis acid catalysis using chiral metal complexes
ES2289140T3 (es) 2001-07-16 2008-02-01 F. Hoffmann-La Roche Ag Derivados de 2-pirrolidona como agonistas de prostanoide.
BR0211201A (pt) 2001-07-16 2004-07-13 Hoffmann La Roche Composto, processo para a preparação desse composto, sua utilização, composição farmacêutica que compreende o mesmo e método para o tratamento de uma enfermidade em um mamìfero
TWI313608B (en) * 2001-07-23 2009-08-21 Ono Pharmaceutical Co Lower bone mass treating agent containing er4 agonist as active ingredient
EP1461026A2 (en) 2001-12-03 2004-09-29 Merck & Co., Inc. Method for treating ocular hypertension
BR0308738A (cg-RX-API-DMAC7.html) 2002-03-18 2005-01-11
CA2488001C (en) 2002-06-06 2011-03-22 Merck Frosst Canada & Co. 1,5-distributed pyrrolid-2-one derivatives for use as ep4 receptor agonists in the treatment of eye diseases such as glaucoma
EP1556347A4 (en) 2002-06-10 2006-08-09 Applied Research Systems GAMMA LACTAME AS PROSTAGLAND INAGONISTS AND THEIR USE
WO2004037786A2 (en) 2002-10-25 2004-05-06 Merck Frosst Canada & Co. 2-pyrrolidones as ep4 receptor agonists
DE602004013559D1 (de) 2003-03-03 2008-06-19 Serono Lab G-lactamderivate als prostaglandinagonisten
CN101868455B (zh) 2007-10-23 2013-11-13 阿勒根公司 治疗性的取代的内酰胺
WO2011003058A1 (en) 2009-07-03 2011-01-06 Concert Pharmaceuticals, Inc. Prostacyclin derivatives
CN103201261A (zh) 2010-11-10 2013-07-10 埃科特莱茵药品有限公司 用作为食欲素受体拮抗剂的内酰胺衍生物
DK2729445T3 (en) * 2011-07-04 2016-01-18 Rottapharm Biotech Srl CYCLIC AMINE DERIVATIVES AS EP4 RECEPTOR ANTAGONISTS

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009023193A1 (en) * 2007-08-15 2009-02-19 Cytokinetics, Incorporated Certain chemical entities, compositions, and methods
WO2014015247A1 (en) * 2012-07-19 2014-01-23 Cayman Chemical Company, Inc. Difluorolactam compounds as ep4 receptor-selective agonists for use in the treatment of ep4-mediated disease and conditions
WO2014015246A1 (en) * 2012-07-19 2014-01-23 Cayman Chemical Company, Inc. Difluorolactam compositions for ep4-mediated osteo related diseases and conditions

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
KONAS D. W. et al., Organic Letters, 1999, Vol. 1, pages 2105-2107 *
MARTINEZ-MONTERO S. et al., Bioorganic & Medicinal Chemistry, 2012, Vol. 20, pages 6885-6893 *
PubChem accession no. CID 66622708; Entry date 30 November 2012 *

Also Published As

Publication number Publication date
IL241042A0 (en) 2015-11-30
CA2903314C (en) 2023-02-14
EP2970234B1 (en) 2018-07-18
US9914725B2 (en) 2018-03-13
US20190202816A1 (en) 2019-07-04
IL241042B (en) 2021-10-31
HK1215022A1 (en) 2016-08-12
EP2970234A2 (en) 2016-01-20
CA2903314A1 (en) 2014-09-18
JP6368351B2 (ja) 2018-08-01
JP2016519669A (ja) 2016-07-07
US20180170918A1 (en) 2018-06-21
US20220127252A9 (en) 2022-04-28
AU2014229065A1 (en) 2015-09-17
US20160060253A1 (en) 2016-03-03
WO2014144500A2 (en) 2014-09-18
WO2014144500A3 (en) 2015-05-28
US11345690B2 (en) 2022-05-31

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