CA2754890C - Bicyclic heterocycles - Google Patents

Bicyclic heterocycles Download PDF

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Publication number
CA2754890C
CA2754890C CA2754890A CA2754890A CA2754890C CA 2754890 C CA2754890 C CA 2754890C CA 2754890 A CA2754890 A CA 2754890A CA 2754890 A CA2754890 A CA 2754890A CA 2754890 C CA2754890 C CA 2754890C
Authority
CA
Canada
Prior art keywords
amino
thiazolo
piperazin
pyrimidin
pyrimidine
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
CA2754890A
Other languages
English (en)
French (fr)
Other versions
CA2754890A1 (en
Inventor
Piet Herdewijn
Steven De Jonghe
Ling-Jie Gao
Mi-Yeon Jang
Bart Vanderhoydonck
Mark Jozef Albert Waer
Yuan Lin
Jean Ferdinand Herman
Thierry Andre Michel Louat
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Katholieke Universiteit Leuven
Original Assignee
Katholieke Universiteit Leuven
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
Priority claimed from GB0904373A external-priority patent/GB0904373D0/en
Priority claimed from GB0904353A external-priority patent/GB0904353D0/en
Priority claimed from GB0911022A external-priority patent/GB0911022D0/en
Application filed by Katholieke Universiteit Leuven filed Critical Katholieke Universiteit Leuven
Priority to CA2987743A priority Critical patent/CA2987743A1/en
Publication of CA2754890A1 publication Critical patent/CA2754890A1/en
Application granted granted Critical
Publication of CA2754890C publication Critical patent/CA2754890C/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
    • C07D473/32—Nitrogen atom
    • 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
    • A61K31/495—Heterocyclic 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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
    • 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
    • A61K31/495—Heterocyclic 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
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic 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
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • 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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
    • A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
    • 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
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Immunology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Rheumatology (AREA)
  • Pain & Pain Management (AREA)
  • Transplantation (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2754890A 2009-03-13 2010-03-15 Bicyclic heterocycles Expired - Fee Related CA2754890C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA2987743A CA2987743A1 (en) 2009-03-13 2010-03-15 Purine derivatives and their use as immunosuppressive agents

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
GB0904373A GB0904373D0 (en) 2009-03-13 2009-03-13 Novel thienopyrimidines
GB0904353A GB0904353D0 (en) 2009-03-13 2009-03-13 Novel thiazolopyrimidines
GB0904353.0 2009-03-13
GB0904373.8 2009-03-13
GB0911022A GB0911022D0 (en) 2009-06-26 2009-06-26 Novel purines
GB0911022.2 2009-06-26
PCT/EP2010/053318 WO2010103130A2 (en) 2009-03-13 2010-03-15 Novel bicyclic heterocycles

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA2987743A Division CA2987743A1 (en) 2009-03-13 2010-03-15 Purine derivatives and their use as immunosuppressive agents

Publications (2)

Publication Number Publication Date
CA2754890A1 CA2754890A1 (en) 2010-09-16
CA2754890C true CA2754890C (en) 2018-01-16

Family

ID=42181129

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2754890A Expired - Fee Related CA2754890C (en) 2009-03-13 2010-03-15 Bicyclic heterocycles
CA2987743A Abandoned CA2987743A1 (en) 2009-03-13 2010-03-15 Purine derivatives and their use as immunosuppressive agents

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA2987743A Abandoned CA2987743A1 (en) 2009-03-13 2010-03-15 Purine derivatives and their use as immunosuppressive agents

Country Status (6)

Country Link
US (2) US8901132B2 (enExample)
EP (2) EP2923734B1 (enExample)
JP (2) JP5647998B2 (enExample)
CA (2) CA2754890C (enExample)
ES (2) ES2543216T3 (enExample)
WO (1) WO2010103130A2 (enExample)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PL2035369T3 (pl) 2006-07-05 2015-02-27 Fibrotech Therapeutics Pty Ltd Związki terapeutyczne
ES2543216T3 (es) * 2009-03-13 2015-08-17 Katholieke Universiteit Leuven, K.U. Leuven R&D Moduladores de tiazolopirimidina como agentes inmunosupresores
CN102574843B (zh) * 2009-10-22 2015-06-17 法博太科制药有限公司 抗纤维化剂的稠环类似物
GB201012889D0 (en) 2010-08-02 2010-09-15 Univ Leuven Kath Antiviral activity of novel bicyclic heterocycles
GB201015411D0 (en) 2010-09-15 2010-10-27 Univ Leuven Kath Anti-cancer activity of novel bicyclic heterocycles
GB201114212D0 (en) 2011-08-18 2011-10-05 Ucb Pharma Sa Therapeutic agents
GB201115665D0 (en) 2011-09-09 2011-10-26 Univ Leuven Kath Autoimmune and inflammatory disorder therapy
US20130102601A1 (en) 2011-10-21 2013-04-25 F. Hoffmann-La Roche Ltd Pyrimidin-4-one derivatives and their use in the treatment, amelioration or prevention of a viral disease
GB201119401D0 (en) 2011-11-10 2011-12-21 Ucb Pharma Sa Therapeutic agents
GB201217704D0 (en) * 2012-10-03 2012-11-14 Ucb Pharma Sa Therapeutic agents
PE20151767A1 (es) * 2012-12-20 2015-12-11 Ucb Biopharma Sprl Derivados de pirazolo-pirimidina terapeuticamente activos
CN103044460B (zh) * 2013-01-30 2015-02-25 石家庄学院 3,5,7-三苯基-5H-噻唑并[3,2-a]嘧啶类衍生物及应用
BR112015025296A2 (pt) * 2013-04-05 2017-07-18 Polichem Sa uso de pidotimod para o tratamento de doença inflamatória intestinal
RU2016110852A (ru) * 2013-09-27 2017-10-30 Нимбус Айрис, Инк. Ингибиторы irak и их применения
TWI648281B (zh) 2013-10-17 2019-01-21 日商安斯泰來製藥股份有限公司 含硫二環式化合物
CN104892589A (zh) * 2014-03-07 2015-09-09 中国科学院上海药物研究所 一类杂环化合物、其制备方法和用途
GB201410817D0 (en) * 2014-06-17 2014-07-30 Ucb Biopharma Sprl And Katholieke Universiteit Leuven K U Leuven R & D Therapeutic agents
US9822127B2 (en) * 2014-07-23 2017-11-21 The Board Of Trustees Of The Leland Stanford Junior University GAK modulators as antivirals
MX2017005462A (es) 2014-11-05 2017-07-28 Flexus Biosciences Inc Agentes inmunorreguladores.
UY36390A (es) 2014-11-05 2016-06-01 Flexus Biosciences Inc Compuestos moduladores de la enzima indolamina 2,3-dioxigenasa (ido), sus métodos de síntesis y composiciones farmacéuticas que los contienen
GB201517263D0 (en) 2015-09-30 2015-11-11 Ucb Biopharma Sprl And Katholieke Universiteit Leuven Therapeutic agents
GB201521767D0 (en) 2015-12-10 2016-01-27 Ucb Biopharma Sprl And Katholieke Universiteit Leuven K U Leuven R&D Therapeutic agents
MX2019009235A (es) 2017-02-03 2019-12-11 Certa Therapeutics Pty Ltd Compuestos antifibroticos.
US11952387B2 (en) 2018-08-21 2024-04-09 Kyorin Pharmaceutical Co., Ltd Bicyclic heteroaromatic ring derivative

Family Cites Families (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2512572A (en) 1950-06-20 Substituted pteridines and method
BE791242A (fr) * 1971-11-11 1973-05-10 Thomae Gmbh Dr K Nouvelles thiazolo(5,4-d)pyrimidines
US4127118B1 (en) 1977-03-16 1995-12-19 Alvaro Latorre Method of effecting and enhancing an erection
ZA857647B (en) * 1984-10-12 1986-05-28 Warner Lambert Co Purine derivatives
US5057517A (en) * 1987-07-20 1991-10-15 Merck & Co., Inc. Piperazinyl derivatives of purines and isosteres thereof as hypoglycemic agents
IL87149A (en) * 1987-07-20 1994-05-30 Merck & Co Inc 6-Piperazinyl derivatives of purine and its 3- and 9-deaza isosteres, their preparation and pharmaceutical compositions containing them
GB9221220D0 (en) 1992-10-09 1992-11-25 Sandoz Ag Organic componds
US5780462A (en) 1995-12-27 1998-07-14 American Home Products Corporation Water soluble rapamycin esters
JP2001097979A (ja) * 1999-07-28 2001-04-10 Takeda Chem Ind Ltd 縮合複素環化合物、その製造法および用途
US6331547B1 (en) 1999-08-18 2001-12-18 American Home Products Corporation Water soluble SDZ RAD esters
DE60101372T2 (de) * 2000-02-11 2004-10-14 Astrazeneca Ab Pyrimidinverbindungen und ihre verwendung als modulatoren der chemokin-rezeptor-aktivität
US6440991B1 (en) 2000-10-02 2002-08-27 Wyeth Ethers of 7-desmethlrapamycin
JP2004028376A (ja) 2002-06-21 2004-01-29 Hino Motors Ltd Ｅｇｒクーラ
JP4768265B2 (ja) * 2002-10-15 2011-09-07 シンタ ファーマシューティカルズ コーポレーション 新規化合物
AU2003302657B8 (en) * 2002-12-04 2009-12-03 Eisai R&D Management Co., Ltd. Fused 1,3-dihydroimidazole ring compounds
ES2217956B1 (es) * 2003-01-23 2006-04-01 Almirall Prodesfarma, S.A. Nuevos derivados de 4-aminotieno(2,3-d)pirimidin-6-carbonitrilo.
ES2324536T7 (es) 2003-06-11 2012-03-16 Xention Limited Derivados de tenopirimidina como inhibidores de los canales de potasio.
DE10348023A1 (de) * 2003-10-15 2005-05-19 Imtm Gmbh Neue Alanyl-Aminopeptidasen-Inhibitoren zur funktionellen Beeinflussung unterschiedlicher Zellen und zur Behandlung immunologischer, entzündlicher, neuronaler und anderer Erkrankungen
US20080269238A1 (en) 2004-04-01 2008-10-30 Takeda Pharmaceutical Company Limited Thiazolopyrimidine Derivative
GB0407723D0 (en) * 2004-04-05 2004-05-12 Novartis Ag Organic compounds
US7576080B2 (en) 2004-12-23 2009-08-18 Memory Pharmaceuticals Corporation Certain thienopyrimidine derivatives as phosphodiesterase 10 inhibitors
FR2880626B1 (fr) * 2005-01-13 2008-04-18 Aventis Pharma Sa Derives de la purine, compositions les contenant et utilisation
EP1844052A1 (en) * 2005-01-26 2007-10-17 Pharmacia & Upjohn Company LLC Thieno[2,3-d]pyrimidine compounds as inhibitors of adp-mediated platelets aggregation
US20090149452A1 (en) 2005-07-01 2009-06-11 Nippon Chemiphar Co., Ltd. Xanthine oxidase inhibitor
GB0526246D0 (en) * 2005-12-22 2006-02-01 Novartis Ag Organic compounds
WO2007084815A2 (en) 2006-01-19 2007-07-26 Janssen Pharmaceutica, N.V. Substituted thienopyrimidine kinase inhibitors
KR100846988B1 (ko) 2006-03-06 2008-07-16 제일약품주식회사 신규한 티에노피리미딘 유도체 또는 이의 약학적으로허용가능한 염, 이의 제조방법 및 이를 함유하는 약학조성물
KR101402474B1 (ko) * 2006-04-26 2014-06-19 제넨테크, 인크. 포스포이노시티드 3-키나제 억제제 화합물 및 이를 포함하는 약학적 조성물
CA2651769C (en) * 2006-05-18 2013-12-17 F. Hoffmann-La Roche Ag Thiazolo-pyramidine / pyridine urea derivatives as adenosine a2b receptor antagonists
WO2008005303A2 (en) 2006-06-30 2008-01-10 Janssen Pharmaceutica N.V. Thiazolopyrimidine modulators of trpv1
ATE485276T1 (de) 2006-08-08 2010-11-15 Millennium Pharm Inc Heteroarylverbindungen als hemmer der e1- aktivierenden enzyme
WO2008057402A2 (en) * 2006-11-02 2008-05-15 Cytovia, Inc. N-aryl-isoxazolopyrimidin-4-amines and related compounds as activators of caspases and inducers of apoptosis and the use thereof
AU2006350748A1 (en) 2006-11-16 2008-05-22 Pharmacopeia, Llc 7-substituted purine derivatives for immunosuppression
WO2008059368A2 (en) 2006-11-17 2008-05-22 Pfizer Products Inc. Fused 2-amino pyrimidine compounds and their use for the treatment of cancer
ES2571028T3 (es) * 2006-12-07 2016-05-23 Genentech Inc Compuestos inhibidores de fosfoinositida 3-cinasa y métodos de uso
CA2674875A1 (en) 2007-01-23 2008-07-31 Palau Pharma, S.A. Purine derivatives
MX2009007944A (es) 2007-01-26 2009-08-07 Irm Llc Compuestos y composiciones de purina como inhibidores de quinasa para el tratamiento de enfermedades relacionadas con plasmodium.
WO2008135232A1 (en) 2007-05-02 2008-11-13 Riccardo Cortese Use and compositions of purine derivatives for the treatment of proliferative disorders
CN101679456B (zh) * 2007-06-12 2012-09-05 霍夫曼-拉罗奇有限公司 噻唑并嘧啶类和它们作为磷脂酰肌醇3-激酶的抑制剂的应用
TWI434849B (zh) 2007-06-29 2014-04-21 Gilead Sciences Inc 類鐸（Ｔｏｌｌ－ｌｉｋｅ）受體７之調節劑
WO2009013545A2 (en) * 2007-07-26 2009-01-29 Astrazeneca Ab Chemical compounds
WO2009027732A1 (en) * 2007-08-24 2009-03-05 Astrazeneca Ab 5-6-bicyclic heteroaromatic compounds with antibacterial activity
CA2704711C (en) * 2007-09-24 2016-07-05 Genentech, Inc. Thiazolopyrimidine p13k inhibitor compounds and methods of use
UA104010C2 (en) * 2008-12-18 2013-12-25 Эли Лилли Энд Компани Purine compounds
ES2543216T3 (es) * 2009-03-13 2015-08-17 Katholieke Universiteit Leuven, K.U. Leuven R&D Moduladores de tiazolopirimidina como agentes inmunosupresores
AR080711A1 (es) * 2010-03-31 2012-05-02 Lilly Co Eli Compuesto de piperazin-purina composicion farmaceutica que lo comprende y su uso para preparar un medicamento util para el tratamiento o prevencion del dolor

Also Published As

Publication number Publication date
WO2010103130A2 (en) 2010-09-16
EP2923734A1 (en) 2015-09-30
US9221822B2 (en) 2015-12-29
ES2543216T3 (es) 2015-08-17
ES2665277T3 (es) 2018-04-25
US8901132B2 (en) 2014-12-02
JP5647998B2 (ja) 2015-01-07
WO2010103130A3 (en) 2010-12-23
JP2015028088A (ja) 2015-02-12
JP6021880B2 (ja) 2016-11-09
CA2754890A1 (en) 2010-09-16
CA2987743A1 (en) 2010-09-16
EP2923734B1 (en) 2018-01-10
US20150038494A1 (en) 2015-02-05
EP2405973A2 (en) 2012-01-18
US20120046278A1 (en) 2012-02-23
JP2012520269A (ja) 2012-09-06
EP2405973B1 (en) 2015-04-22

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