CA2746307C - Aminopyridine and carboxypyridine compounds as phosphodiesterase 10 inhibitors - Google Patents

Aminopyridine and carboxypyridine compounds as phosphodiesterase 10 inhibitors Download PDF

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Publication number
CA2746307C
CA2746307C CA2746307A CA2746307A CA2746307C CA 2746307 C CA2746307 C CA 2746307C CA 2746307 A CA2746307 A CA 2746307A CA 2746307 A CA2746307 A CA 2746307A CA 2746307 C CA2746307 C CA 2746307C
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CA
Canada
Prior art keywords
pyridin
compound
pharmaceutically acceptable
acceptable salt
ylamino
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
CA2746307A
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English (en)
French (fr)
Other versions
CA2746307A1 (en
Inventor
Jennifer R. Allen
Ning Chen
James R. Falsey
Michael Frohn
Paul Harrington
Essa Hu
Matthew R. Kaller
Roxanne Kunz
Stephanie J. Mercede
Thomas T. Nguyen
Alexander J. Pickrell
Andreas Reichelt
Shannon Rumfelt
Robert M. Rzasa
Kelvin Sham
Aaron C. Siegmund
Christopher M. Tegley
Guomin Yao
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Amgen Inc
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Amgen Inc
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Publication of CA2746307A1 publication Critical patent/CA2746307A1/en
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Publication of CA2746307C publication Critical patent/CA2746307C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/02—Heterocyclic 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 two hetero rings
    • C07D401/04—Heterocyclic 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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • 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
    • A61P25/08—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
    • A61P25/24—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
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/32—Alcohol-abuse
    • 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
    • A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
    • A61P25/36—Opioid-abuse
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/72—Nitrogen atoms
    • C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/84—Nitriles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/02—Heterocyclic 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 two hetero rings
    • C07D401/12—Heterocyclic 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 two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic 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
    • C07D401/14—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic 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
    • C07D407/14—Heterocyclic 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
    • 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
    • C07D409/14—Heterocyclic 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic 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

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Neurology (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Psychiatry (AREA)
  • Addiction (AREA)
  • Psychology (AREA)
  • Pain & Pain Management (AREA)
  • Hospice & Palliative Care (AREA)
  • Dermatology (AREA)
  • Pulmonology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
CA2746307A 2008-12-17 2009-12-16 Aminopyridine and carboxypyridine compounds as phosphodiesterase 10 inhibitors Expired - Fee Related CA2746307C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US13843408P 2008-12-17 2008-12-17
US13844308P 2008-12-17 2008-12-17
US61/138,443 2008-12-17
US61/138,434 2008-12-17
PCT/US2009/068330 WO2010077992A1 (en) 2008-12-17 2009-12-16 Aminopyridine and carboxypyridine compounds as phosphodiesterase 10 inhibitors

Publications (2)

Publication Number Publication Date
CA2746307A1 CA2746307A1 (en) 2010-07-08
CA2746307C true CA2746307C (en) 2013-11-19

Family

ID=41718257

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2746307A Expired - Fee Related CA2746307C (en) 2008-12-17 2009-12-16 Aminopyridine and carboxypyridine compounds as phosphodiesterase 10 inhibitors

Country Status (10)

Country Link
US (1) US8637500B2 (https=)
EP (1) EP2376455B1 (https=)
JP (1) JP2012512255A (https=)
AR (1) AR074775A1 (https=)
AU (1) AU2009333214B2 (https=)
CA (1) CA2746307C (https=)
ES (1) ES2397934T3 (https=)
MX (1) MX2011006575A (https=)
TW (1) TW201035051A (https=)
WO (1) WO2010077992A1 (https=)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9051296B2 (en) 2009-11-16 2015-06-09 Raqualia Pharma Inc. Aryl carboxamide derivatives as TTX-S blockers
US8470820B2 (en) * 2010-01-22 2013-06-25 Hoffman-La Roche Inc. Nitrogen-containing heteroaryl derivatives
EP2601192B1 (en) * 2010-08-04 2017-03-01 Takeda Pharmaceutical Company Limited Fused heterocyclic compounds
CN103476757A (zh) 2011-02-18 2013-12-25 阿勒根公司 作为磷酸二酯酶10(pde10a)的抑制剂的取代的6,7-二烷氧基-3-异喹啉醇衍生物
EP2714041B1 (en) * 2011-05-24 2016-10-19 Merck Sharp & Dohme Corp. Aryloxymethyl cyclopropane derivatives as pde10 inhibitors
BR112013033375B1 (pt) * 2011-06-27 2022-05-10 Janssen Pharmaceutica N.V Derivados de 1-aril-4-metil-[1,2,4]triazolo[4,3-a]quinoxa-lina, seu uso, composição farmacêutica que os compreende, processo de preparação dos mesmos, solução estéril e composto intermediário
DK2748151T3 (en) * 2011-08-25 2016-07-04 Merck Sharp & Dohme Pyrimidine-pde10 inhibitors
US8470884B2 (en) 2011-11-09 2013-06-25 Hoffmann-La Roche Inc. Alkenyl naphthylacetic acids
WO2013148537A1 (en) * 2012-03-29 2013-10-03 Ning Xi Substituted spirobicyclic compounds and methods of use
ES2670667T3 (es) 2012-05-15 2018-05-31 Novartis Ag Derivados de benzamida para inhibir la actividad de ABL1, ABL2 y BCR-ABL1
HK1206250A1 (en) 2012-06-26 2016-01-08 Janssen Pharmaceutica Nv Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl-[1,2,4] triazolo [4,3-a] quinoxaline compounds and ped 10 inhibitors for use in the treatment of neurological or metabolic disorders
WO2014071044A1 (en) 2012-11-01 2014-05-08 Allergan, Inc. Substituted 6,7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (pde10a)
US9200016B2 (en) 2013-12-05 2015-12-01 Allergan, Inc. Substituted 6, 7-dialkoxy-3-isoquinoline derivatives as inhibitors of phosphodiesterase 10 (PDE 10A)
SG11201801856XA (en) 2015-09-18 2018-04-27 Kaken Pharmaceutical Co Ltd Biaryl derivative and medicine containing same
EA202092441A1 (ru) 2016-06-07 2021-05-21 Джакобио Фармасьютикалс Ко., Лтд. Новые гетероциклические производные, применимые в качестве ингибиторов shp2
EP3527570A4 (en) 2016-10-14 2020-04-15 Jiangsu Hengrui Medicine Co., Ltd. FIVE-LINKED HETERARYARYLE CYCLE BRIDGE DERIVATIVE, METHOD FOR PREPARING SAME, AND MEDICAL USE THEREOF
KR20240026521A (ko) 2017-03-23 2024-02-28 자코바이오 파마슈티칼스 컴퍼니 리미티드 Shp2 억제제로서 유용한 신규한 헤테로환형 유도체
JP7234201B2 (ja) * 2017-07-12 2023-03-07 ブリストル－マイヤーズ スクイブ カンパニー 心不全の治療のためのｒｏｃｋの５員アミノヘテロ環および５，６－または６，６員二環式アミノヘテロ環の阻害剤
CN108997230B (zh) * 2018-07-26 2020-08-04 山东大学 具有基质金属蛋白酶抑制活性的喹喔啉衍生物及其制备方法和应用
CN112839935A (zh) 2018-09-26 2021-05-25 北京加科思新药研发有限公司 可用作shp2抑制剂的新型杂环衍生物
CN116583577B (zh) 2020-12-17 2025-10-21 默克专利股份有限公司 杂芳族异硫氰酸酯
JP2025515208A (ja) * 2022-05-09 2025-05-13 ティーワイケー メディシンズ インコーポレーテッド 多環式化合物およびその使用
WO2025024681A1 (en) * 2023-07-25 2025-01-30 The Regents Of The University Of California Ire1alpha inhibitors and uses thereof
WO2025024688A1 (en) * 2023-07-25 2025-01-30 The Regents Of The University Of California Ire1alpha inhibitors and uses thereof

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4107288A (en) 1974-09-18 1978-08-15 Pharmaceutical Society Of Victoria Injectable compositions, nanoparticles useful therein, and process of manufacturing same
US4198417A (en) 1979-01-10 1980-04-15 American Hoechst Corporation Phenoxyphenylpiperidines
PT72878B (en) 1980-04-24 1983-03-29 Merck & Co Inc Process for preparing mannich-base hydroxamic acid pro-drugs for the improved delivery of non-steroidal anti-inflammatory agents
US5145684A (en) 1991-01-25 1992-09-08 Sterling Drug Inc. Surface modified drug nanoparticles
WO2001056990A2 (en) 2000-02-03 2001-08-09 Eli Lilly And Company Pyridine derivates as potentiators of glutamate receptors
WO2001087845A2 (en) * 2000-05-15 2001-11-22 Fujisawa Pharmaceutical Co., Ltd. N-containing heterocyclic compounds and their use as 5-ht antagonists
PT1635828E (pt) 2003-04-04 2008-07-01 Lundbeck & Co As H Derivados de 4-(2-feniloxifenil) piperidina ou de 1,2,3,6-tetrahidropiridina como inibidores da recaptação da serotonina
EP1651251A4 (en) 2003-07-31 2008-06-18 Bayer Pharmaceuticals Corp METHOD FOR THE TREATMENT OF DIABETES AND RELATED DISEASES USING PDE 10A INHIBITORS
JP2007504229A (ja) 2003-09-02 2007-03-01 メルク　エンド　カムパニー　インコーポレーテッド 代謝調節型グルタミン酸受容体−５のモジュレーターとしてのビピリジルアミン類およびエーテル類
US20050250820A1 (en) * 2004-03-08 2005-11-10 Amgen Inc. Therapeutic modulation of PPARgamma activity
US20060019975A1 (en) 2004-07-23 2006-01-26 Pfizer Inc Novel piperidyl derivatives of quinazoline and isoquinoline
NL2000397C2 (nl) 2006-01-05 2007-10-30 Pfizer Prod Inc Bicyclische heteroarylverbindingen als PDE10 inhibitoren.
AU2007208351C1 (en) 2006-01-23 2011-07-07 Amgen Inc. Aurora kinase modulators and method of use
US7560551B2 (en) * 2006-01-23 2009-07-14 Amgen Inc. Aurora kinase modulators and method of use
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
WO2008057280A1 (en) 2006-10-27 2008-05-15 Amgen Inc. Multi-cyclic compounds and methods of use
ES2392156T3 (es) 2006-12-20 2012-12-05 Amgen Inc. Heterociclos sustituidos y métodos de uso
WO2009081259A1 (en) 2007-12-21 2009-07-02 Pfizer Inc. Phenoxy-pyridyl derivatives
MX2010013876A (es) 2008-06-20 2011-03-04 Metabolex Inc Agonistas de arilo grpr119 y sus usos .
TWI396689B (zh) * 2008-11-14 2013-05-21 Amgen Inc 作為磷酸二酯酶１０抑制劑之吡衍生物

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Publication number Publication date
JP2012512255A (ja) 2012-05-31
AU2009333214B2 (en) 2013-09-26
US20100160280A1 (en) 2010-06-24
WO2010077992A1 (en) 2010-07-08
AU2009333214A1 (en) 2011-06-30
US8637500B2 (en) 2014-01-28
CA2746307A1 (en) 2010-07-08
TW201035051A (en) 2010-10-01
AR074775A1 (es) 2011-02-09
MX2011006575A (es) 2011-10-06
ES2397934T3 (es) 2013-03-12
EP2376455A1 (en) 2011-10-19
EP2376455B1 (en) 2012-11-14

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