JP5746972B2 - ホスホジエステラーゼ10阻害剤としてのピラジン化合物 - Google Patents

ホスホジエステラーゼ10阻害剤としてのピラジン化合物 Download PDF

Info

Publication number
JP5746972B2
JP5746972B2 JP2011536567A JP2011536567A JP5746972B2 JP 5746972 B2 JP5746972 B2 JP 5746972B2 JP 2011536567 A JP2011536567 A JP 2011536567A JP 2011536567 A JP2011536567 A JP 2011536567A JP 5746972 B2 JP5746972 B2 JP 5746972B2
Authority
JP
Japan
Prior art keywords
benzo
pyrazin
alkyl
phenyl
yloxy
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
JP2011536567A
Other languages
English (en)
Japanese (ja)
Other versions
JP2012508776A5 (enExample
JP2012508776A (ja
Inventor
アレン,ジエニフアー・アール
ブルボー,マシユー・ピー
チエン,ニン
フー,エツサ
クンツ,ロクサーヌ
ラムフエルト,シヤノン
Original Assignee
アムジエン・インコーポレーテツド
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 アムジエン・インコーポレーテツド filed Critical アムジエン・インコーポレーテツド
Publication of JP2012508776A publication Critical patent/JP2012508776A/ja
Publication of JP2012508776A5 publication Critical patent/JP2012508776A5/ja
Application granted granted Critical
Publication of JP5746972B2 publication Critical patent/JP5746972B2/ja
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/4965Non-condensed pyrazines
    • A61K31/497Non-condensed pyrazines containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/14Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16Anti-Parkinson drugs
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/18Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/24Antidepressants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/28Drugs 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/30Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/36Opioid-abuse
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/04Anorexiants; Antiobesity agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00Drugs for disorders of the metabolism
    • A61P3/08Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D403/00Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D407/00Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/14Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D409/00Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D413/00Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/14Heterocyclic 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 three or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D471/00Heterocyclic 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
    • C07D471/02Heterocyclic 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
    • C07D471/04Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Diabetes (AREA)
  • Addiction (AREA)
  • Hematology (AREA)
  • Psychology (AREA)
  • Obesity (AREA)
  • Emergency Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Child & Adolescent Psychology (AREA)
  • Endocrinology (AREA)
  • Pain & Pain Management (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
JP2011536567A 2008-11-14 2009-11-16 ホスホジエステラーゼ10阻害剤としてのピラジン化合物 Expired - Fee Related JP5746972B2 (ja)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US11456708P 2008-11-14 2008-11-14
US61/114,567 2008-11-14
US16621209P 2009-04-02 2009-04-02
US61/166,212 2009-04-02
PCT/US2009/064637 WO2010057121A1 (en) 2008-11-14 2009-11-16 Pyrazine compounds as phosphodiesterase 10 inhibitors

Publications (3)

Publication Number Publication Date
JP2012508776A JP2012508776A (ja) 2012-04-12
JP2012508776A5 JP2012508776A5 (enExample) 2014-12-04
JP5746972B2 true JP5746972B2 (ja) 2015-07-08

Family

ID=41478512

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2011536567A Expired - Fee Related JP5746972B2 (ja) 2008-11-14 2009-11-16 ホスホジエステラーゼ10阻害剤としてのピラジン化合物

Country Status (30)

Country Link
US (4) US8053438B2 (enExample)
EP (1) EP2364308B1 (enExample)
JP (1) JP5746972B2 (enExample)
KR (1) KR20110083746A (enExample)
CN (1) CN102300860B (enExample)
AR (1) AR074358A1 (enExample)
AU (1) AU2009313768B2 (enExample)
BR (1) BRPI0922095A2 (enExample)
CA (1) CA2742993C (enExample)
CL (1) CL2011001094A1 (enExample)
CO (1) CO6382157A2 (enExample)
CR (1) CR20110326A (enExample)
CY (1) CY1113680T1 (enExample)
DK (1) DK2364308T3 (enExample)
EA (1) EA019206B1 (enExample)
ES (1) ES2397218T3 (enExample)
HR (1) HRP20130054T1 (enExample)
IL (1) IL212687A0 (enExample)
MA (1) MA32889B1 (enExample)
MX (1) MX2011005100A (enExample)
NZ (1) NZ592508A (enExample)
PE (1) PE20110581A1 (enExample)
PL (1) PL2364308T3 (enExample)
PT (1) PT2364308E (enExample)
RS (1) RS52598B (enExample)
SI (1) SI2364308T1 (enExample)
SM (1) SMT201200061B (enExample)
TN (1) TN2011000221A1 (enExample)
TW (1) TWI396689B (enExample)
WO (1) WO2010057121A1 (enExample)

Families Citing this family (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9156812B2 (en) 2008-06-04 2015-10-13 Bristol-Myers Squibb Company Crystalline form of 6-[(4S)-2-methyl-4-(2-naphthyl)-1,2,3,4-tetrahydroisoquinolin-7-yl]pyridazin-3-amine
US8637500B2 (en) * 2008-12-17 2014-01-28 Amgen Inc. Aminopyridine and carboxypyridine compounds as phosphodiesterase 10 inhibitors
KR101730665B1 (ko) 2009-02-05 2017-04-26 다케다 야쿠힌 고교 가부시키가이샤 피리다지논 화합물
WO2010132442A1 (en) * 2009-05-12 2010-11-18 Albany Molecular Reserch, Inc. 7-([1,2,4,]triazolo[1,5,-a]pyridin-6-yl)-4-(3,4-dichlorophenyl)-1,2,3,4- tetrahydroisoquinoline and use thereof
MX2011011900A (es) 2009-05-12 2012-01-20 Squibb Bristol Myers Co Formas cristalinas de (s)-7-([1,2,4]triazolo[1,5-a]piridin-6-il)-4 -(3,4-diclorofenil)-1,2,3,4-tetrahidroisoquinolina y usos de las misma.
PH12012501661A1 (en) 2010-02-19 2012-10-22 Boehringer Ingelheim Int Tricyclic pyridine derivatives, medicaments containing such compounds, their use and process for their preparation
TWI546302B (zh) 2010-06-24 2016-08-21 武田藥品工業股份有限公司 稠合雜環化合物
JP5760085B2 (ja) * 2010-08-04 2015-08-05 武田薬品工業株式会社 縮合複素環化合物
US8883788B2 (en) 2010-08-04 2014-11-11 Takeda Pharmaceutical Company Limited Fused heterocyclic ring compound
EP2604597B1 (en) 2010-08-10 2017-01-04 Takeda Pharmaceutical Company Limited Heterocyclic compound and use thereof inhibitor of phosphodiesterase 10a
CN108864151A (zh) 2010-11-19 2018-11-23 利亘制药公司 杂环胺及其用途
CA2824047C (en) 2011-01-11 2019-06-18 Sunovion Pharmaceuticals Inc. Heteroaryl compounds and methods of use thereof
EP2687529B1 (en) 2011-03-16 2016-07-13 Takeda Pharmaceutical Company Limited Condensed heterocyclic compound
TWI570122B (zh) 2011-06-22 2017-02-11 武田藥品工業股份有限公司 稠合雜環化合物之結晶
US9750705B2 (en) * 2012-08-31 2017-09-05 The Regents Of The University Of California Agents useful for treating obesity, diabetes and related disorders
CN102911135B (zh) * 2012-10-18 2016-01-13 内蒙古工业大学 2-巯基苯并噻唑类衍生物的合成方法
JP6208261B2 (ja) 2013-02-05 2017-10-04 パーデュー、ファーマ、リミテッド、パートナーシップPurdue Pharma L.P. タンパリング抵抗性医薬製剤
EP2975037A4 (en) 2013-03-15 2016-08-10 Daiichi Sankyo Co Ltd benzothiophene derivative
WO2015006689A1 (en) 2013-07-12 2015-01-15 University Of South Alabama Treatment and diagnosis of cancer and precancerous conditions using pde10a inhibitors and methods to measure pde10a expression
RU2016110852A (ru) 2013-09-27 2017-10-30 Нимбус Айрис, Инк. Ингибиторы irak и их применения
US9657015B2 (en) 2014-07-31 2017-05-23 Boehringer Ingelheim International Gmbh Substituted bicyclic dihydropyrimidinones and their use as inhibitors of neutrophil elastase activity
CN104649882A (zh) * 2015-02-11 2015-05-27 南通恒盛精细化工有限公司 一种磷酸二酯酶抑制剂的中间体制备工艺
US10807983B2 (en) 2015-03-16 2020-10-20 Ligand Pharmaceuticals, Inc. Imidazo-fused heterocycles and uses thereof
RU2760373C2 (ru) * 2015-09-18 2021-11-24 Какен Фармасьютикал Ко., Лтд. Биарильное производное и содержащее его лекарственное средство
CA3088932A1 (en) * 2018-01-19 2019-07-25 Suzhou Sinovent Pharmaceuticals Co., Ltd. Heterocyclic compound, preparation method and use thereof in medicine
CN109020977B (zh) * 2018-10-26 2020-11-13 安庆奇创药业有限公司 一种Acalabrutinib的制备方法
JP2023553699A (ja) 2020-12-17 2023-12-25 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング ヘテロ芳香族イソチオシアネート類
CN113929598A (zh) * 2021-11-24 2022-01-14 上海吉奉生物科技有限公司 一种(s)-2-叔丁氧羰基氨基-3-(4,4-二氟环己基)丙酸的合成方法
EP4524134A1 (en) * 2022-05-09 2025-03-19 TYK Medicines Inc. Polycyclic compound and use thereof
CN115894181A (zh) * 2022-09-30 2023-04-04 渭南高新区海泰新型电子材料有限责任公司 一种环己烯基环己基二氟苯类液晶化合物的合成方法

Family Cites Families (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4198417A (en) 1979-01-10 1980-04-15 American Hoechst Corporation Phenoxyphenylpiperidines
US20060293360A1 (en) 2003-04-04 2006-12-28 H. Lundbeck A/S 4-(2-Phenyloxyphenyl)-piperidine or-1,2,3,6-tetrahydropyridine derivatives as serotonin reuptake inhibitors
DE10337942A1 (de) 2003-08-18 2005-03-17 Merck Patent Gmbh Aminobenzimidazolderivate
DE10344223A1 (de) 2003-09-24 2005-04-21 Merck Patent Gmbh 1,3-Benzoxazolylderivate als Kinase-Inhibitoren
DE10349587A1 (de) 2003-10-24 2005-05-25 Merck Patent Gmbh Benzimidazolylderivate
US7470712B2 (en) 2004-01-21 2008-12-30 Bristol-Myers Squibb Company Amino-benzazoles as P2Y1 receptor inhibitors
CN1984901B (zh) * 2004-05-18 2011-02-09 先灵公司 用作pde4抑制剂的取代的2-喹啉基-*唑
BRPI0511854A (pt) * 2004-06-07 2008-01-15 Pfizer Prod Inc inibição de fosfodiestearase 10 como tratamento para condições relacionados com a obesidade e relacionadas a sìndrome metabólica
US20060183763A1 (en) * 2004-12-31 2006-08-17 Pfizer Inc Novel pyrrolidyl derivatives of heteroaromatic compounds
DE102005016634A1 (de) 2005-04-12 2006-10-19 Merck Patent Gmbh Neuartige Aza-Hetercyclen als Kinase-Inhibitoren
WO2007016228A2 (en) 2005-08-02 2007-02-08 Irm Llc 5-substituted thiazol-2-yl amino compounds and compositions as protein kinase inhibitors
JP2009527560A (ja) 2006-02-21 2009-07-30 アムゲン インコーポレイティッド ホスホジエステラーゼ10阻害剤としてのシンノリン誘導体
US7868177B2 (en) 2006-02-24 2011-01-11 Amgen Inc. Multi-cyclic compounds and method of use
CA2650976A1 (en) * 2006-05-02 2007-11-15 Pfizer Products Inc. Bicyclic heteroaryl compounds as pde10 inhibitors
US20080090834A1 (en) 2006-07-06 2008-04-17 Pfizer Inc Selective azole pde10a inhibitor compounds
US8236823B2 (en) 2006-10-27 2012-08-07 Amgen Inc. Multi-cyclic compounds and methods of use
ATE502028T1 (de) * 2006-12-21 2011-04-15 Pfizer Prod Inc Succinatsalz von 2-((4-(1-methyl-4(pyridin-4-yl)- 1h-pyrazol-3-yl)phenoxy)methyl)chinolin
CA2703653A1 (en) 2007-10-25 2009-04-30 Astrazeneca Ab Pyridine and pyrazine derivatives -083
WO2009081259A1 (en) 2007-12-21 2009-07-02 Pfizer Inc. Phenoxy-pyridyl derivatives
US20110294836A1 (en) 2008-06-20 2011-12-01 Metabolex, Inc. Aryl gpr119 agonists and uses thereof

Also Published As

Publication number Publication date
US20100137278A1 (en) 2010-06-03
TW201030006A (en) 2010-08-16
DK2364308T3 (da) 2013-02-04
KR20110083746A (ko) 2011-07-20
SI2364308T1 (sl) 2013-01-31
ES2397218T3 (es) 2013-03-05
CO6382157A2 (es) 2012-02-15
RS52598B (sr) 2013-04-30
AU2009313768B2 (en) 2013-01-10
US20110160202A1 (en) 2011-06-30
SMT201200061B (it) 2013-01-14
CN102300860A (zh) 2011-12-28
CA2742993C (en) 2015-01-20
PL2364308T3 (pl) 2013-03-29
PT2364308E (pt) 2013-01-08
US20120277209A1 (en) 2012-11-01
US8247418B2 (en) 2012-08-21
EA019206B1 (ru) 2014-01-30
HK1161251A1 (en) 2012-08-24
US8053438B2 (en) 2011-11-08
EP2364308A1 (en) 2011-09-14
AU2009313768A1 (en) 2010-05-20
CL2011001094A1 (es) 2011-11-11
EA201100748A1 (ru) 2011-10-31
TWI396689B (zh) 2013-05-21
WO2010057121A1 (en) 2010-05-20
BRPI0922095A2 (pt) 2019-09-24
CN102300860B (zh) 2014-08-27
CR20110326A (es) 2011-07-28
US8329700B2 (en) 2012-12-11
CY1113680T1 (el) 2016-06-22
IL212687A0 (en) 2011-07-31
HRP20130054T1 (hr) 2013-02-28
JP2012508776A (ja) 2012-04-12
US20110160182A1 (en) 2011-06-30
MA32889B1 (fr) 2011-12-01
NZ592508A (en) 2013-04-26
CA2742993A1 (en) 2010-05-20
MX2011005100A (es) 2011-05-30
TN2011000221A1 (en) 2012-12-17
AR074358A1 (es) 2011-01-12
EP2364308B1 (en) 2012-10-24
PE20110581A1 (es) 2011-09-03

Similar Documents

Publication Publication Date Title
JP5746972B2 (ja) ホスホジエステラーゼ10阻害剤としてのピラジン化合物
EP2364306B1 (en) Pyridine and pyrimidine derivatives as phosphodiesterase 10 inhibitors
US8497265B2 (en) Heteroaryloxyheterocyclyl compounds as PDE10 inhibitors
US8952037B2 (en) Heteroaryloxycarbocyclyl compounds as PDE10 inhibitors
AU2011253003A1 (en) Heteroaryloxyheterocyclyl compounds as PDE10 inhibitors
JP2013526524A (ja) Pde10阻害剤としてのアリールおよびヘテロアリール窒素ヘテロ環式化合物
HK1161251B (en) Pyrazine compounds as phosphodiesterase 10 inhibitors

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20120705

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20120705

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20140107

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20140513

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20140812

A602 Written permission of extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A602

Effective date: 20140819

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20141010

A524 Written submission of copy of amendment under article 19 pct

Free format text: JAPANESE INTERMEDIATE CODE: A524

Effective date: 20141010

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20150414

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20150511

R150 Certificate of patent or registration of utility model

Ref document number: 5746972

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

LAPS Cancellation because of no payment of annual fees