JP2017513913A - 光学活性なｐｄｅ１０阻害剤 - Google Patents

光学活性なｐｄｅ１０阻害剤 Download PDF

Info

Publication number
JP2017513913A
JP2017513913A JP2016564604A JP2016564604A JP2017513913A JP 2017513913 A JP2017513913 A JP 2017513913A JP 2016564604 A JP2016564604 A JP 2016564604A JP 2016564604 A JP2016564604 A JP 2016564604A JP 2017513913 A JP2017513913 A JP 2017513913A
Authority
JP
Japan
Prior art keywords
compound
formula
disorder
converting
acid
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.)
Pending
Application number
JP2016564604A
Other languages
English (en)
Japanese (ja)
Other versions
JP2017513913A5 (enExample
Inventor
ニール エス． カッツホール，
ニール エス． カッツホール，
ケネス エム． ファーガソン，
ケネス エム． ファーガソン，
チャールズ プリンス ズタ，
チャールズ プリンス ズタ，
Original Assignee
オメロス コーポレーション
オメロス コーポレーション
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 オメロス コーポレーション, オメロス コーポレーション filed Critical オメロス コーポレーション
Publication of JP2017513913A publication Critical patent/JP2017513913A/ja
Publication of JP2017513913A5 publication Critical patent/JP2017513913A5/ja
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/433—Thidiazoles
    • 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
    • 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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • A61P25/22—Anxiolytics
    • 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
    • A61P25/24—Antidepressants
    • 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
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • 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
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Psychology (AREA)
  • Epidemiology (AREA)
  • Hospice & Palliative Care (AREA)
  • Anesthesiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
JP2016564604A 2014-04-28 2015-04-24 光学活性なｐｄｅ１０阻害剤 Pending JP2017513913A (ja)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US201461985381P 2014-04-28 2014-04-28
US61/985,381 2014-04-28
US201462047569P 2014-09-08 2014-09-08
US62/047,569 2014-09-08
PCT/US2015/027645 WO2015167968A1 (en) 2014-04-28 2015-04-24 Optically active pde10 inhibitor

Publications (2)

Publication Number Publication Date
JP2017513913A true JP2017513913A (ja) 2017-06-01
JP2017513913A5 JP2017513913A5 (enExample) 2018-05-31

Family

ID=54359189

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2016564604A Pending JP2017513913A (ja) 2014-04-28 2015-04-24 光学活性なｐｄｅ１０阻害剤

Country Status (13)

Country Link
US (2) US9493447B2 (enExample)
EP (1) EP3137461B1 (enExample)
JP (1) JP2017513913A (enExample)
KR (1) KR102558505B1 (enExample)
CN (1) CN106255690B (enExample)
AU (1) AU2015253463B2 (enExample)
BR (1) BR112016024523B1 (enExample)
CA (1) CA2946754C (enExample)
ES (1) ES2895487T3 (enExample)
IL (1) IL248586B (enExample)
NZ (2) NZ716462A (enExample)
RU (1) RU2016146097A (enExample)
WO (1) WO2015167968A1 (enExample)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017513885A (ja) * 2014-04-28 2017-06-01 オメロス コーポレーション Ｐｄｅ１０阻害剤の調製のための方法および中間体

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ601967A (en) * 2010-03-12 2015-03-27 Omeros Corp Pde10 inhibitors and related compositions and methods
NZ716462A (en) * 2014-04-28 2017-11-24 Omeros Corp Optically active pde10 inhibitor
US20160284909A1 (en) * 2015-03-27 2016-09-29 Gabriel Harley Multi-diode solar cells
CN107530313A (zh) * 2015-04-24 2018-01-02 奥默罗斯公司 Pde10抑制剂以及相关组合物和方法
WO2017079678A1 (en) 2015-11-04 2017-05-11 Omeros Corporation Solid state forms of a pde10 inhibitor

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013522228A (ja) * 2010-03-12 2013-06-13 オメロス コーポレーション Ｐｄｅ１０インヒビターならびに関連する組成物および方法
JP6474430B2 (ja) * 2014-04-28 2019-02-27 オメロス コーポレーション Ｐｄｅ１０阻害剤の調製のための方法および中間体

Family Cites Families (70)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DK178590D0 (da) 1990-07-26 1990-07-26 Novo Nordisk As 1,4-disubstituerede piperaziner
PT100905A (pt) 1991-09-30 1994-02-28 Eisai Co Ltd Compostos heterociclicos azotados biciclicos contendo aneis de benzeno, ciclo-hexano ou piridina e de pirimidina, piridina ou imidazol substituidos e composicoes farmaceuticas que os contem
BR9307570A (pt) 1992-12-02 1999-05-25 Pfizer Diéteres de catecol como inibidores seletivos de pdeiv
DE4323192A1 (de) 1993-07-10 1995-01-12 Basf Ag Verfahren zur Herstellung von Homo- und Copolymerisaten von Alk-1-enen
DE4325846C1 (de) 1993-07-31 1995-01-19 Herberts Gmbh Verwendung von Furan-modifizierten aromatischen Pinakolderivaten als Initiatoren und Furan-modifizierte aromatische Pinakolderivate als solche
DE4343286A1 (de) 1993-12-17 1995-06-22 Hoechst Ag Heteroaromatische Verbindungen und ihre Verwendung in flüssigkristallinen Mischungen
DE4409501A1 (de) 1994-03-19 1995-09-21 Didier Werke Ag Verschleißfutter eines Schachtofens und Stein hierfür
CA2193725A1 (en) 1994-06-24 1996-01-04 David Cavalla Aryl derivative compounds and uses to inhibit phosphodiesterase iv acti vity
US5789434A (en) 1994-11-15 1998-08-04 Bayer Corporation Derivatives of substituted 4-biarylbutyric acid as matrix metalloprotease inhibitors
TW424087B (en) 1995-04-06 2001-03-01 Janssen Pharmaceutica Nv 1,3-dihydro-1-(phenylalkenyl)-2H-imidazol-2-one derivatives
TW332201B (en) 1995-04-06 1998-05-21 Janssen Pharmaceutica Nv 1,3-Dihydro-1-(phenylalkyl)-2H-imidazol-2-one derivatives
US6037370A (en) 1995-06-08 2000-03-14 Vertex Pharmaceuticals Incorporated Methods and compositions for stimulating neurite growth
JP2000503984A (ja) 1996-01-22 2000-04-04 藤沢薬品工業株式会社 チアゾリルベンゾフラン誘導体およびその医薬組成物
AU4015497A (en) 1996-08-26 1998-03-19 Byk Gulden Lomberg Chemische Fabrik Gmbh Thiazole derivatives useful as selective inhibitors of pde-iv
JPH1087543A (ja) 1996-09-17 1998-04-07 Chisso Corp アルコキシベンゼン誘導体、液晶組成物および液晶表示素子
US6548490B1 (en) 1997-10-28 2003-04-15 Vivus, Inc. Transmucosal administration of phosphodiesterase inhibitors for the treatment of erectile dysfunction
WO1999045914A1 (en) 1998-03-13 1999-09-16 Maruho Kabushikikaisha Alkyl amine derivative and local anesthetic agent using the same
GB9807354D0 (en) * 1998-04-07 1998-06-03 Glaxo Group Ltd Antiviral compound
SE9804212D0 (sv) 1998-12-04 1998-12-04 Astra Pharma Prod Compounds
WO2000034251A1 (en) 1998-12-07 2000-06-15 Smithkline Beecham Corporation A method for quantitative determination of amino acids
HUP0202248A3 (en) 1999-03-12 2006-06-28 Boehringer Ingelheim Pharma Compounds useful as anti-inflammatory agents
US7141593B1 (en) * 1999-06-04 2006-11-28 Abbott Laboratories Pharmaceutical formulations
GB9929552D0 (en) 1999-12-14 2000-02-09 Proteus Molecular Design Compounds
US6933304B2 (en) 2000-06-15 2005-08-23 Pharmacia Corporation Heteroarylalkanoic acids as integrin receptor antagonists
US20030032579A1 (en) 2001-04-20 2003-02-13 Pfizer Inc. Therapeutic use of selective PDE10 inhibitors
IL158591A0 (en) * 2001-05-22 2004-05-12 Pfizer Prod Inc Crystal forms of azithromycin
US6821502B2 (en) * 2002-06-12 2004-11-23 Chevron U.S.A. Inc. Method of making aluminum-containing zeolite with IFR structure
JP2005533858A (ja) 2002-07-27 2005-11-10 アストラゼネカ アクチボラグ 化合物
AU2003275493A1 (en) 2002-10-08 2004-05-04 The Scripps Research Institute Inhibitors of fatty acid amide hydrolase
WO2004041258A2 (fr) 2002-10-30 2004-05-21 Neuro3D Utilisation d’inhibiteurs des phosphodiesterases des nucleotides cycliques, ayant une structure benzodiazepinique en therapie
TW200410921A (en) 2002-11-25 2004-07-01 Hoffmann La Roche Mandelic acid derivatives
US20060040986A1 (en) 2002-12-06 2006-02-23 Kowa Co., Ltd. Erythropoietin production accelerator
US20050043344A1 (en) 2002-12-20 2005-02-24 Pharmacia Corporation Heteroarylalkanoic acids as integrin receptor antagonists derivatives
WO2004071509A1 (ja) 2003-02-12 2004-08-26 Nippon Chemiphar Co., Ltd. オリゴデンドロサイト分化促進剤
KR20060005375A (ko) 2003-04-18 2006-01-17 메모리 파마슈티칼스 코포레이션 포스포디에스테라제 4 억제제로서의 피라졸 유도체
AR047541A1 (es) * 2004-02-13 2006-01-25 Sandoz Ag Fosfato de 5-[[4-[2-metil-2-piridinil-amino-etoxi]fenil]metil]-2,4 tiazolidinadiona (rosiglitazona) y sus formas polimorficas
MXPA06012130A (es) 2004-04-20 2007-01-31 Transtech Pharma Inc Derivados de tiazol y pirimidina substituidos como moduladores del receptor de melanocortina.
JP2007537296A (ja) * 2004-05-14 2007-12-20 アボット・ラボラトリーズ 治療薬としてのキナーゼ阻害薬
US7351833B2 (en) * 2004-07-23 2008-04-01 Abbott Laboratories (1S,5S)-3-(5,6-dichloropyridin-3-yl)-3,6-diazabicyclo[3.2.0]heptane benzenesulfonate
US7449486B2 (en) * 2004-10-19 2008-11-11 Array Biopharma Inc. Mitotic kinesin inhibitors and methods of use thereof
US8436176B2 (en) * 2004-12-30 2013-05-07 Medicis Pharmaceutical Corporation Process for preparing 2-methyl-1-(2-methylpropyl)-1H-imidazo[4,5-c][1,5]naphthyridin-4-amine
EA012211B1 (ru) 2005-01-07 2009-08-28 Пфайзер Продактс Инк. Гетероароматические соединения хинолинов и их применение в качестве ингибиторов pde10
MX2007009388A (es) 2005-02-04 2007-09-25 Senomyx Inc Compuestos que comprenden porciones heteroarilo unidas y su uso como modificadores del sabor unami, saborizantes y mejoradores del sabor para composiciones comestibles.
AR056319A1 (es) 2005-04-22 2007-10-03 Kalypsys Inc Inhibidores de orto-terfinilo de p38 quinasa, composicion farmaceutica y compuestos intermedios
UA91546C2 (uk) * 2005-05-03 2010-08-10 Бьорінгер Інгельхайм Інтернаціональ Гмбх КРИСТАЛІЧНА ФОРМА 1-ХЛОР-4-(β-D-ГЛЮКОПІРАНОЗ-1-ИЛ)-2-[4-((S)-ТЕТРАГІДРОФУРАН-3-ІЛОКСИ)-БЕНЗИЛ]-БЕНЗОЛУ, СПОСІБ ЇЇ ОДЕРЖАННЯ ТА ЇЇ ЗАСТОСУВАННЯ ПРИ ПРИГОТУВАННІ ЛІКАРСЬКИХ ЗАСОБІВ
MY152185A (en) * 2005-06-10 2014-08-29 Novartis Ag Modified release 1-[(3-hydroxy-adamant-1-ylamino)-acetyl]-pyrrolidine-2(s)-carbonitrile formulation
CA2617788A1 (en) 2005-08-04 2007-02-15 Apogee Biotechnology Corporation Sphingosine kinase inhibitors and methods of their use
JP5063600B2 (ja) * 2005-08-29 2012-10-31 サノフイ−アベンテイス・ユー・エス・エルエルシー ピリダジノ［４，５−ｂ］インドール誘導体の新規な結晶形
KR20070085703A (ko) * 2005-09-13 2007-08-27 시코르, 인크. 로큐로늄 브로마이드의 합성 방법
AU2006316079B2 (en) 2005-11-15 2012-03-29 Otsuka Pharmaceutical Co., Ltd. Oxazole compound and pharmaceutical composition
CN101341131A (zh) 2005-12-23 2009-01-07 阿斯利康(瑞典)有限公司 作为gaba-b受体调节剂的咪唑
JP2009535394A (ja) 2006-05-02 2009-10-01 ファイザー・プロダクツ・インク Ｐｄｅ１０阻害剤としての二環式ヘテロアリール化合物
US20080090834A1 (en) 2006-07-06 2008-04-17 Pfizer Inc Selective azole pde10a inhibitor compounds
CN101568331A (zh) 2006-09-08 2009-10-28 奥尔制药有限公司 减少或缓解消化道炎症的方法
SG10201609581TA (en) * 2006-09-25 2016-12-29 Ptc Therapeutics Inc Crystalline forms of 3-[5-(2-fluorophenyl)-[1,2,4]oxadiazol-3-yl]-benzoic acid
CA2663569A1 (en) * 2006-09-28 2008-04-03 Merck & Co., Inc. Pharmaceutical compositions of hdac inhibitors and chelatable metal compounds, and metal-hdac inhibitor chelate complexes
US20090253918A1 (en) 2006-10-02 2009-10-08 Janssen Pharmaceuticals, N.V. Novel intermediate for glyt1 inhibitor
US7837978B2 (en) * 2006-10-13 2010-11-23 Chevron U.S.A. Inc. Process for preparing aluminum-containing molecular sieve SSZ-26
US7786139B2 (en) * 2006-11-21 2010-08-31 Omeros Corporation PDE10 inhibitors and related compositions and methods
EP2083819B1 (en) 2006-11-21 2017-02-22 Omeros Corporation Pde10 inhibitors and related compositions and methods
PE20081506A1 (es) * 2006-12-12 2008-12-09 Infinity Discovery Inc Formulaciones de ansamicina
WO2009008906A2 (en) 2007-02-06 2009-01-15 The Trustees Of The University Of Pennsylvania Therapeutic compounds for blocking dna synthesis of pox viruses
WO2008143500A1 (en) * 2007-05-22 2008-11-27 Ultimorphix Technologies B.V. Tenofovir disoproxil hemi-fumaric acid co-crystal
EP2017264A1 (de) 2007-07-16 2009-01-21 Bayer Cropscience Ag Substituierte Phenylpropargylverbindungen, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
WO2009049022A1 (en) 2007-10-10 2009-04-16 Ore Pharmaceuticals Inc. Method for treatment of pancreatitis
TW200944520A (en) * 2008-01-29 2009-11-01 Glaxo Group Ltd Spiro compounds as NPY Y5 receptor antagonists
WO2009143178A2 (en) 2008-05-20 2009-11-26 Omeros Corporation Pde10 inhibitors and related compositions and methods
TWI501965B (zh) 2008-06-20 2015-10-01 Lundbeck & Co As H 作為ｐｄｅ１０ａ酵素抑制劑之新穎苯基咪唑衍生物
CN102143752B (zh) * 2008-08-05 2014-12-10 奥默罗斯公司 Pde10抑制剂以及相关组合物和方法
NZ716462A (en) * 2014-04-28 2017-11-24 Omeros Corp Optically active pde10 inhibitor

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013522228A (ja) * 2010-03-12 2013-06-13 オメロス コーポレーション Ｐｄｅ１０インヒビターならびに関連する組成物および方法
JP6474430B2 (ja) * 2014-04-28 2019-02-27 オメロス コーポレーション Ｐｄｅ１０阻害剤の調製のための方法および中間体

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BERNARD HULIN ET AL: "Hypoglycemic Activity of a Series of α-Alkylthio and α-Alkoxy Carboxylic Acids Related to Ciglitaz", J. MED. CHEM., vol. 39, no. 20, JPN6019008030, 1996, pages 3897 - 3907, ISSN: 0003991651 *
平山令明編, 有機化合物結晶作製ハンドブック −原理とノウハウ−, JPN6011053065, 25 July 2008 (2008-07-25), pages 57 - 84, ISSN: 0004178028 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2017513885A (ja) * 2014-04-28 2017-06-01 オメロス コーポレーション Ｐｄｅ１０阻害剤の調製のための方法および中間体

Also Published As

Publication number Publication date
EP3137461B1 (en) 2021-08-11
US9493447B2 (en) 2016-11-15
IL248586A0 (en) 2016-12-29
CN106255690B (zh) 2020-07-17
CA2946754A1 (en) 2015-11-05
KR20160141845A (ko) 2016-12-09
EP3137461A1 (en) 2017-03-08
ES2895487T3 (es) 2022-02-21
US9850238B2 (en) 2017-12-26
RU2016146097A (ru) 2018-05-30
WO2015167968A1 (en) 2015-11-05
US20160024070A1 (en) 2016-01-28
NZ630803A (en) 2016-03-31
AU2015253463B2 (en) 2018-12-06
RU2016146097A3 (enExample) 2018-11-15
BR112016024523B1 (pt) 2022-10-11
US20170096420A1 (en) 2017-04-06
CN106255690A (zh) 2016-12-21
IL248586B (en) 2019-09-26
NZ716462A (en) 2017-11-24
KR102558505B1 (ko) 2023-07-21
EP3137461A4 (en) 2017-09-13
BR112016024523A2 (pt) 2017-08-15
CA2946754C (en) 2022-08-30
AU2015253463A1 (en) 2016-11-03

Similar Documents

Publication Publication Date Title
TW495498B (en) Amide derivative and a pharmaceutical composition containing the same as a Ca2+ release activated Ca2+ channel inhibitor
KR102558505B1 (ko) 광학 활성 pde10 저해제
Ohashi et al. Discovery of the investigational drug TAK-441, a pyrrolo [3, 2-c] pyridine derivative, as a highly potent and orally active hedgehog signaling inhibitor: modification of the core skeleton for improved solubility
AU2014249050B2 (en) Histone dementhylase inhibitors
CA2891976C (en) Imidazopyridine compounds
RU2545456C2 (ru) Pde10 ингибиторы и содержащие их композиции и способы
CA2802216C (en) Tetrahydrocarboline derivative and its use as an enpp2 inhibitor
JP2008526966A (ja) β−セクレターゼの阻害のためのアミノ−イミダゾロン
AU2011204370B2 (en) Hedgehog inhibitors
EP3590920A1 (en) 2-(substituted benzene matrix) aromatic formate fto inhibitor, preparation method therefor, and applications thereof
WO2015189433A1 (en) Pyridazinones for the treatment of cancer
CN114685520B (zh) 三并环化合物及其药物组合物和应用
JP2018513153A (ja) Ｐｄｅ１０インヒビターならびに関連する組成物および方法
US9650368B2 (en) Processes and intermediates for the preparation of a PDE10 inhibitor
HK1235766B (en) Method of preparing an optically active pde10 inhibitor
HK1235766A1 (en) Method of preparing an optically active pde10 inhibitor
WO2023031246A1 (en) Substituted thiophene compounds as d-dopachrome tautomerase inhibitors
CN103923078A (zh) 3,4-二取代(1H-吡唑[3,4-b]吡啶)类化合物及其用途
JPWO2019088057A1 (ja) アニリド誘導体及びその医薬用途
KR20230056618A (ko) Stat3 저해제로서 벤조싸이오펜-1,1-다이옥사이드 유도체 화합물 및 이의 용도
WO2023187471A1 (en) Heteroaryl derivative compounds, and uses thereof

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20180413

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20180413

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20190306

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20190603

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20190906

A02 Decision of refusal

Free format text: JAPANESE INTERMEDIATE CODE: A02

Effective date: 20191219