KR101399766B1 - 키나제 조절제로서 유용한 융합된 헤테로시클릭 화합물 - Google Patents

키나제 조절제로서 유용한 융합된 헤테로시클릭 화합물 Download PDF

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Publication number
KR101399766B1
KR101399766B1 KR1020087009516A KR20087009516A KR101399766B1 KR 101399766 B1 KR101399766 B1 KR 101399766B1 KR 1020087009516 A KR1020087009516 A KR 1020087009516A KR 20087009516 A KR20087009516 A KR 20087009516A KR 101399766 B1 KR101399766 B1 KR 101399766B1
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South Korea
Prior art keywords
aminocyclohexyl
trans
imidazo
pyridazine
diamine
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Expired - Fee Related
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KR1020087009516A
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Korean (ko)
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KR20080063344A (ko
Inventor
웨인 바카로
종 첸
다름팔 에스. 도드
트램 엔. 후인
제임스 린
춘지안 리우
크리스토퍼 피. 무사리
존 에스. 토카르스키
데이비드 알. 토르톨라니
스티븐 티. 브로블레스키
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브리스톨-마이어스 스큅 컴퍼니
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Application filed by 브리스톨-마이어스 스큅 컴퍼니 filed Critical 브리스톨-마이어스 스큅 컴퍼니
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D487/00Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04Ortho-condensed systems
    • 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
    • A61K31/435Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/18Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/06Antiasthmatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/12Drugs for disorders of the urinary system of the kidneys
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • A61P17/06Antipsoriatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/02Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/06Antigout agents, e.g. antihyperuricemic or uricosuric agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00Drugs for skeletal disorders
    • A61P19/08Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00Drugs for disorders of the muscular or neuromuscular system
    • A61P21/04Drugs for disorders of the muscular or neuromuscular system for myasthenia gravis
    • 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
    • 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
    • A61P25/28Drugs 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
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12Antivirals
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • A61P35/02Antineoplastic agents specific for leukemia
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/08Antiallergic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00Drugs for disorders of the blood or the extracellular fluid
    • A61P7/06Antianaemics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00Drugs for disorders of the cardiovascular system
    • A61P9/10Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

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  • 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)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Neurology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurosurgery (AREA)
  • Rheumatology (AREA)
  • Pulmonology (AREA)
  • Diabetes (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Hematology (AREA)
  • Immunology (AREA)
  • Dermatology (AREA)
  • Urology & Nephrology (AREA)
  • Oncology (AREA)
  • Pain & Pain Management (AREA)
  • Cardiology (AREA)
  • Emergency Medicine (AREA)
  • Obesity (AREA)
  • Endocrinology (AREA)
  • Psychiatry (AREA)
  • Psychology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hospice & Palliative Care (AREA)
  • Vascular Medicine (AREA)
  • Communicable Diseases (AREA)
  • Virology (AREA)
KR1020087009516A 2005-09-22 2006-09-22 키나제 조절제로서 유용한 융합된 헤테로시클릭 화합물 Expired - Fee Related KR101399766B1 (ko)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US71951905P 2005-09-22 2005-09-22
US60/719,519 2005-09-22
US11/524,996 2006-09-21
US11/524,996 US20070078136A1 (en) 2005-09-22 2006-09-21 Fused heterocyclic compounds useful as kinase modulators
PCT/US2006/037056 WO2007038314A2 (en) 2005-09-22 2006-09-22 Fused heterocyclic compounds useful as kinase modulators

Related Child Applications (1)

Application Number Title Priority Date Filing Date
KR1020147007661A Division KR20140058645A (ko) 2005-09-22 2006-09-22 키나제 조절제로서 유용한 융합된 헤테로시클릭 화합물

Publications (2)

Publication Number Publication Date
KR20080063344A KR20080063344A (ko) 2008-07-03
KR101399766B1 true KR101399766B1 (ko) 2014-06-18

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ID=37716206

Family Applications (2)

Application Number Title Priority Date Filing Date
KR1020147007661A Withdrawn KR20140058645A (ko) 2005-09-22 2006-09-22 키나제 조절제로서 유용한 융합된 헤테로시클릭 화합물
KR1020087009516A Expired - Fee Related KR101399766B1 (ko) 2005-09-22 2006-09-22 키나제 조절제로서 유용한 융합된 헤테로시클릭 화합물

Family Applications Before (1)

Application Number Title Priority Date Filing Date
KR1020147007661A Withdrawn KR20140058645A (ko) 2005-09-22 2006-09-22 키나제 조절제로서 유용한 융합된 헤테로시클릭 화합물

Country Status (24)

Country Link
US (1) US20070078136A1 (enExample)
EP (1) EP1928879B1 (enExample)
JP (1) JP5241498B2 (enExample)
KR (2) KR20140058645A (enExample)
AR (1) AR055177A1 (enExample)
AU (1) AU2006295439B2 (enExample)
BR (1) BRPI0616393B8 (enExample)
CA (1) CA2623369C (enExample)
CY (1) CY1114001T1 (enExample)
DK (1) DK1928879T3 (enExample)
EA (1) EA017632B1 (enExample)
ES (1) ES2402664T3 (enExample)
GE (1) GEP20104943B (enExample)
HR (1) HRP20130155T1 (enExample)
IL (1) IL190280A (enExample)
NO (1) NO20081231L (enExample)
NZ (1) NZ566663A (enExample)
PE (1) PE20070520A1 (enExample)
PH (1) PH12013501329B1 (enExample)
PL (1) PL1928879T3 (enExample)
PT (1) PT1928879E (enExample)
SI (1) SI1928879T1 (enExample)
TW (2) TWI478925B (enExample)
WO (1) WO2007038314A2 (enExample)

Families Citing this family (129)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR062207A1 (es) 2006-08-04 2008-10-22 Takeda Pharmaceutical Derivados de imidazopiridazina inhibidores de quinasas utiles para prevenir y/o tratar el cancer.
EP2125819B1 (en) * 2007-03-21 2014-10-22 Bristol-Myers Squibb Company Fused heterocyclic compounds useful for the treatment of proliferative, allergic, autoimmune or inflammatory diseases
AR067326A1 (es) * 2007-05-11 2009-10-07 Novartis Ag Imidazopiridinas y pirrolo -pirimidinas sustituidas como inhibidores de cinasa de lipido
CA2694261A1 (en) * 2007-07-26 2009-01-29 Novartis Ag Organic compounds
EP2222639A1 (en) * 2007-11-21 2010-09-01 Decode Genetics EHF Biaryl pde4 inhibitors for treating pulmonary and cardiovascular disorders
WO2009067604A1 (en) * 2007-11-21 2009-05-28 Decode Genetics Ehf Substituted benzoazole pde4 inhibitors for treating inflammatory, cardiovascular and cns disorders
JP5693239B2 (ja) * 2008-01-23 2015-04-01 ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company 4−ピリジノン化合物および癌についてのその使用
WO2009100375A1 (en) * 2008-02-06 2009-08-13 Bristol-Myers Squibb Company Substituted imidazopyridazines useful as kinase inhibitors
UY31676A1 (es) 2008-02-28 2009-09-30 "derivados de 3-metil-imidiazo-[1,2-b]-piridazina"
AU2009226024B2 (en) * 2008-03-20 2012-07-12 Amgen Inc. Aurora kinase modulators and method of use
BRPI0912668A2 (pt) * 2008-05-13 2016-01-26 Irm Llc composto e composições como inibidores de quinase
WO2010036407A2 (en) * 2008-05-15 2010-04-01 Biocryst Pharmaceuticals, Inc. Antiviral nucleoside analogs
NZ602791A (en) * 2008-05-21 2014-04-30 Incyte Corp Salts of 2-fluoro-n-methyl-4-[7-(quinolin-6-yl-methyl)- imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide and processes related to preparing the same
JP2011529073A (ja) * 2008-07-24 2011-12-01 ブリストル−マイヤーズ スクイブ カンパニー キナーゼ調節因子として有用な縮合ヘテロ環化合物
UY32049A (es) * 2008-08-14 2010-03-26 Takeda Pharmaceutical Inhibidores de cmet
WO2010027114A1 (en) * 2008-09-05 2010-03-11 Choongwae Pharma Corporation Use of pyrazole-pyridine derivatives and its salts for treating or reventin osteoporosis
EP2350075B1 (en) 2008-09-22 2014-03-05 Array Biopharma, Inc. Substituted imidazo[1,2b]pyridazine compounds as trk kinase inhibitors
TWI491610B (zh) 2008-10-09 2015-07-11 必治妥美雅史谷比公司 作為激酶抑制劑之咪唑并嗒腈
KR101853026B1 (ko) 2008-10-22 2018-04-27 어레이 바이오파마 인크. TRK 키나아제 억제제로서 치환된 피라졸로[1,5­a] 피리미딘 화합물
WO2010068810A2 (en) * 2008-12-10 2010-06-17 Cgi Pharmaceuticals, Inc. Certain substituted amides, method of making, and method of use thereof
PA8854101A1 (es) * 2008-12-18 2010-07-27 Ortho Mcneil Janssen Pharm Derivados de imidazol bicíclicos sustituidos como moduladores de gamma secretasa
SG171815A1 (en) 2008-12-19 2011-07-28 Bristol Myers Squibb Co Carbazole carboxamide compounds useful as kinase inhibitors
WO2010074284A1 (ja) 2008-12-26 2010-07-01 味の素株式会社 ピラゾロピリミジン化合物
AU2010211109B2 (en) 2009-02-06 2014-11-27 Cellzome Limited Novel substituted bicyclic heterocyclic compounds as gamma secretase modulators
TWI461425B (zh) 2009-02-19 2014-11-21 Janssen Pharmaceuticals Inc 作為伽瑪分泌酶調節劑之新穎經取代的苯并唑、苯并咪唑、唑并吡啶及咪唑并吡啶衍生物類
MX2011011753A (es) 2009-05-07 2011-11-29 Janssen Pharmaceuticals Inc Nuevos derivados sustitutos de indazol y aza-indazol como moduladores de la gamma secretasa.
ES2444777T3 (es) 2009-06-12 2014-02-26 Bristol-Myers Squibb Company Compuestos de nicotinamida útiles como moduladores de quinasas
AR077468A1 (es) 2009-07-09 2011-08-31 Array Biopharma Inc Compuestos de pirazolo (1,5 -a) pirimidina sustituidos como inhibidores de trk- quinasa
CA2778517A1 (en) 2009-07-15 2011-01-20 Janssen Pharmaceuticals, Inc. Substituted triazole and imidazole derivatives as gamma secretase modulators
US8389526B2 (en) 2009-08-07 2013-03-05 Novartis Ag 3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives
NZ599597A (en) * 2009-10-30 2013-05-31 Janssen Pharmaceutica Nv IMIDAZO[1,2-b]PYRIDAZINE DERIVATIVES AND THEIR USE AS PDE10 INHIBITORS
JPWO2011078221A1 (ja) 2009-12-24 2013-05-09 味の素株式会社 イミダゾピリダジン化合物
PH12012501381A1 (en) 2010-01-15 2012-10-22 Janssen Pharmaceuticals Inc Novel substituted bicyclic triazole derivatives as gamma secretase modulators
CA2787714C (en) 2010-01-22 2019-04-09 Joaquin Pastor Fernandez Inhibitors of pi3 kinase
AR080754A1 (es) 2010-03-09 2012-05-09 Janssen Pharmaceutica Nv Derivados de imidazo (1,2-a) pirazina y su uso como inhibidores de pde10
EP2563792B1 (en) 2010-04-28 2014-08-27 Bristol-Myers Squibb Company Imidazopyridazinyl compounds and their uses for cancer
US20130131057A1 (en) 2010-05-13 2013-05-23 Centro Nacional De Investigaciones Oncologicas (Cnio New bicyclic compounds as pi3-k and mtor inhibitors
CN105693720B (zh) 2010-05-20 2019-01-18 阵列生物制药公司 作为trk激酶抑制剂的大环化合物
EP2582668B1 (en) 2010-06-16 2016-01-13 Bristol-Myers Squibb Company Carboline carboxamide compounds useful as kinase inhibitors
CA2806655A1 (en) 2010-07-28 2012-02-02 Bayer Intellectual Property Gmbh Substituted imidazo[1,2-b]pyridazines
UY33597A (es) 2010-09-09 2012-04-30 Irm Llc Compuestos y composiciones como inhibidores de la trk
TWI541243B (zh) * 2010-09-10 2016-07-11 拜耳知識產權公司 經取代咪唑并嗒
JP2013542259A (ja) 2010-11-12 2013-11-21 ブリストル−マイヤーズ スクイブ カンパニー 置換アザインダゾール化合物
CA2821817A1 (en) 2010-12-17 2012-06-21 Bayer Intellectual Property Gmbh Substituted 6-imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment of hyperproliferative disorders
CN103370322B (zh) 2010-12-17 2016-02-10 拜耳知识产权有限责任公司 在过度增殖性病症的治疗中用作mps-1和tkk抑制剂的2-取代的咪唑并吡嗪
US20130303532A1 (en) 2010-12-17 2013-11-14 Bayer Intellectual Property Gmbh Imidazopyrazines for use as mps-1 and tkk inhibitors in the treatment hyperproliferative disorders
MX2013010970A (es) 2011-03-24 2013-10-17 Cellzome Ltd Novedosos derivados de triazolil piperazina y triazolil piperidina sustituidos como moduladores de gamma-secretasa.
GB201108003D0 (en) 2011-05-13 2011-06-29 Materialise Dental Nv Endodontic treatment simulation system
WO2012156367A1 (en) 2011-05-17 2012-11-22 Bayer Intellectual Property Gmbh Amino-substituted imidazopyridazines as mknk1 kinase inhibitors
CN103717604B (zh) 2011-06-01 2016-06-01 拜耳知识产权有限责任公司 取代的氨基咪唑并哒嗪
CN103764656A (zh) * 2011-06-22 2014-04-30 拜耳知识产权有限责任公司 杂环基氨基咪唑并哒嗪
WO2013000924A1 (en) 2011-06-27 2013-01-03 Janssen Pharmaceutica Nv 1-ARYL-4-METHYL-[1,2,4]TRIAZOLO[4,3-a]QUINOXALINE DERIVATIVES
EA023045B1 (ru) 2011-07-15 2016-04-29 Янссен Фармасьютикалз, Инк. Новые замещенные производные индола в качестве модуляторов гамма-секретазы
WO2013012915A1 (en) 2011-07-19 2013-01-24 Infinity Pharmaceuticals Inc. Heterocyclic compounds and uses thereof
CN103814029B (zh) 2011-09-23 2016-10-12 拜耳知识产权有限责任公司 取代的咪唑并哒嗪
WO2013049263A1 (en) 2011-09-27 2013-04-04 Bristol-Myers Squibb Company Substituted bicyclic heteroaryl compounds
RU2662443C2 (ru) 2011-11-01 2018-07-26 Ф. Хоффманн-Ля Рош Аг Имидазопиридазины
WO2013104573A1 (en) 2012-01-10 2013-07-18 F. Hoffmann-La Roche Ag Pyridazine amide compounds and their use as syk inhibitors
EP2822559B1 (en) * 2012-03-09 2018-05-02 Lexicon Pharmaceuticals, Inc. Imidazo[1,2-b]pyridazine-based compounds, compositions comprising them, and uses thereof
EP2825540B1 (en) 2012-03-14 2016-09-14 Bayer Intellectual Property GmbH Substituted imidazopyridazines
MX355164B (es) 2012-05-16 2018-04-06 Janssen Pharmaceuticals Inc Derivados de 3,4-dihidro-2h-pirido[1,2-a]pirazin-1,6-diona sustituidos utiles para el tratamiento de la enfermedad de alzheimer (inter alia).
WO2014001314A1 (en) 2012-06-26 2014-01-03 Janssen Pharmaceutica Nv Combinations comprising pde 2 inhibitors such as 1-aryl-4-methyl- [1,2,4] triazolo [4,3-a] quinoxaline compounds and pde 10 inhibitors for use in the treatment of neurological or metabolic disorders
AU2013289284B2 (en) 2012-07-09 2017-03-30 Janssen Pharmaceutica Nv Inhibitors of phosphodiesterase 10 enzyme
TW201414737A (zh) 2012-07-13 2014-04-16 必治妥美雅史谷比公司 作爲激酶抑制劑之咪唑并三□甲腈
WO2014020041A1 (en) 2012-08-02 2014-02-06 Bayer Pharma Aktiengesellschaft Combinations for the treatment of cancer
US9428511B2 (en) 2012-09-06 2016-08-30 Bristol-Myers Squibb Company Imidazopyridazine JAK3 inhibitors and their use for the treatment of inflammatory and autoimmune diseases
AU2013344716B2 (en) 2012-11-16 2018-03-01 University Health Network Pyrazolopyrimidine compounds
ES2608356T3 (es) 2012-12-20 2017-04-10 Janssen Pharmaceutica Nv Novedosos derivados tricíclicos de 3,4-dihidro-2H-pirido[1,2-a]pirazin-1,6-diona como moduladores de la secretasa gamma
WO2014100533A1 (en) * 2012-12-21 2014-06-26 Bristol-Myers Squibb Company NOVEL SUBSTITUTED IMIDAZOLES AS CASEIN KINASE 1 δ/ε INHIBITORS
JP6283688B2 (ja) 2012-12-21 2018-02-21 ブリストル−マイヤーズ スクイブ カンパニーBristol−Myers Squibb Company カゼインキナーゼ1d/e阻害剤としての新規なピラゾール置換のイミダゾピラジン
AU2014206834B2 (en) 2013-01-17 2017-06-22 Janssen Pharmaceutica Nv Novel substituted pyrido-piperazinone derivatives as gamma secretase modulators
US9586958B2 (en) 2013-06-11 2017-03-07 Bayer Pharma Aktiengesellschaft Prodrug derivatives of substituted triazolopyridines
WO2014200885A1 (en) 2013-06-11 2014-12-18 Janssen Pharmaceutica Nv PDE10a INHIBITORS FOR THE TREATMENT OF TYPE II DIABETES
US9193736B2 (en) 2013-06-11 2015-11-24 Janssen Pharmaceutica, Nv PDE 10a inhibitors for the treatment of type II diabetes
AR096721A1 (es) 2013-06-25 2016-01-27 Bristol Myers Squibb Co Compuestos de tetrahidrocarbazol y carbazol carboxamida sustituidos
BR112015031432A2 (pt) 2013-06-25 2017-07-25 Bristol Myers Squibb Co compostos de carbazol carboxamida úteis como inibidores de cinase
US9453002B2 (en) 2013-08-16 2016-09-27 Janssen Pharmaceutica Nv Substituted imidazoles as N-type calcium channel blockers
AR097543A1 (es) * 2013-09-06 2016-03-23 Lexicon Pharmaceuticals Inc COMPUESTOS BASADOS EN IMIDAZO[1,2-b]PIRIDAZINA, COMPOSICIONES QUE LOS COMPRENDEN Y SUS MÉTODOS DE USO
ES2702126T3 (es) * 2013-12-10 2019-02-27 Bristol Myers Squibb Co Compuestos de imidazopiridazina útiles como moduladores de respuestas a IL-12, IL-23 y/o IFN alfa
WO2015097121A1 (en) 2013-12-23 2015-07-02 Norgine B.V. Compounds useful as ccr9 modulators
US10562897B2 (en) 2014-01-16 2020-02-18 Janssen Pharmaceutica Nv Substituted 3,4-dihydro-2H-pyrido[1,2-a]pyrazine-1,6-diones as gamma secretase modulators
TW201613927A (en) 2014-09-01 2016-04-16 Bayer Pharma AG Method for preparation of substituted imidazopyridazines
CN110511209B (zh) 2014-10-24 2022-07-05 百时美施贵宝公司 可用作激酶抑制剂的吲哚甲酰胺化合物
TWI746426B (zh) 2014-11-16 2021-11-21 美商亞雷生物製藥股份有限公司 (S)-N-(5-((R)-2-(2,5-二氟苯基)-吡咯啶-1-基)-吡唑并[1,5-a]嘧啶-3-基)-3-羥基吡咯啶-1-甲醯胺硫酸氫鹽結晶型
KR101635173B1 (ko) 2014-12-03 2016-06-30 충남직물공업협동조합 디지털프린팅 날염 친환경 자카드직물의 제조방법 및 그 직물
CN107108633B (zh) 2014-12-19 2020-05-12 詹森药业有限公司 作为PI3Kβ抑制剂的杂环基连接的咪唑并哒嗪衍生物
BR112017012930A2 (pt) 2014-12-19 2018-01-09 Janssen Pharmaceutica Nv derivados de imidazopiridazina como inibidores de pi3kbeta.
CA2978170C (en) 2015-03-09 2024-02-27 Aurigene Discovery Technologies Limited Pyrazolo[1,5-a][1,3,5]triazine and pyrazolo[1,5-a]pyrimidine derivatives as cdk inhibitors
WO2017070089A1 (en) 2015-10-19 2017-04-27 Incyte Corporation Heterocyclic compounds as immunomodulators
TN2018000138A1 (en) 2015-10-26 2019-10-04 Array Biopharma Inc Point mutations in trk inhibitor-resistant cancer and methods relating to the same
DK3377488T3 (da) 2015-11-19 2022-10-03 Incyte Corp Heterocykliske forbindelser som immunomodulatorer
MY199705A (en) 2015-12-22 2023-11-20 Incyte Corp Heterocyclic compounds as immunomodulators
US10045991B2 (en) 2016-04-04 2018-08-14 Loxo Oncology, Inc. Methods of treating pediatric cancers
HUE068971T2 (hu) 2016-04-04 2025-02-28 Loxo Oncology Inc (S)-N-(5-((R)-2-(2,5-difluorofenil)-pirrolidin-1-il)-pirazolo[1,5-A]pirimidin-3-il) -3-hidroxipirrolidin-1-karboxamid folyékony készítményei
TW201808950A (zh) 2016-05-06 2018-03-16 英塞特公司 作為免疫調節劑之雜環化合物
SI3458456T1 (sl) 2016-05-18 2021-04-30 Loxo Oncology, Inc. Priprava (S)-N-(5-((R)-2-(2,5-difluorofenil) pirolidin-1-il) pirazolo (1,5-A) pirimidin-3-il)-3-hidroksipirolidin-1-karboksamida
US20170342060A1 (en) 2016-05-26 2017-11-30 Incyte Corporation Heterocyclic compounds as immunomodulators
WO2017210399A1 (en) * 2016-06-02 2017-12-07 Celgene Corporation Animal and human anti-malarial agents
SG11201811414TA (en) 2016-06-20 2019-01-30 Incyte Corp Heterocyclic compounds as immunomodulators
EP3484866B1 (en) 2016-07-14 2022-09-07 Incyte Corporation Heterocyclic compounds as immunomodulators
MA46045A (fr) 2016-08-29 2021-04-28 Incyte Corp Composés hétérocycliques utilisés comme immunomodulateurs
JOP20190092A1 (ar) 2016-10-26 2019-04-25 Array Biopharma Inc عملية لتحضير مركبات بيرازولو[1، 5-a]بيريميدين وأملاح منها
ES2849974T3 (es) * 2016-11-17 2021-08-24 Bristol Myers Squibb Co Moduladores de imidazopiridazina de IL-12, IL-23 y/o IFNalfa
WO2018109667A1 (en) 2016-12-15 2018-06-21 Nestec Sa Compositions and methods that modulate white blood cells or neutrophils in a companion animal
WO2018119266A1 (en) 2016-12-22 2018-06-28 Incyte Corporation Benzooxazole derivatives as immunomodulators
WO2018119236A1 (en) 2016-12-22 2018-06-28 Incyte Corporation Triazolo[1,5-a]pyridine derivatives as immunomodulators
WO2018119221A1 (en) 2016-12-22 2018-06-28 Incyte Corporation Pyridine derivatives as immunomodulators
US20180179202A1 (en) 2016-12-22 2018-06-28 Incyte Corporation Heterocyclic compounds as immunomodulators
JOP20190213A1 (ar) 2017-03-16 2019-09-16 Array Biopharma Inc مركبات حلقية ضخمة كمثبطات لكيناز ros1
RU2770363C2 (ru) 2017-04-05 2022-04-15 Куровир Аб Гетероароматические соединения, пригодные в терапии
CA3059939A1 (en) * 2017-04-21 2018-10-25 Kyn Therapeutics Indole ahr inhibitors and uses thereof
US11046698B2 (en) * 2017-07-28 2021-06-29 Nimbus Lakshmi, Inc. TYK2 inhibitors and uses thereof
WO2019169249A1 (en) * 2018-03-01 2019-09-06 The Johns Hopkins University INHIBITION OF nSMase FOR THE TREATMENT OF HUMAN IMMUNODEFICIENCY VIRUS INFECTION
FI3774791T3 (fi) 2018-03-30 2023-03-21 Incyte Corp Heterosyklisiä yhdisteitä immunomodulaattoreina
BR112020022936A2 (pt) 2018-05-11 2021-02-02 Incyte Corporation derivados de tetra-hidro-imidazo[4,5-c]piridina como imunomoduladores de pd-l1
KR102813547B1 (ko) 2018-07-27 2025-05-27 코크리스탈 파마, 아이엔씨. 인플루엔자바이러스 복제 억제제로서의 피롤로[2,3-b]피리딘 유도체
CA3126034A1 (en) * 2019-01-23 2020-07-30 Nimbus Lakshmi, Inc. Tyk2 inhibitors and uses thereof
EP3935058B1 (en) * 2019-03-05 2024-08-21 Bristol-Myers Squibb Company Imidazopyridazine compounds useful as modulators of il-12, il-23 and/or ifn alpha responses
CA3139161A1 (en) * 2019-05-17 2020-11-26 Kinnate Biopharma Inc. Inhibitors of fibroblast growth factor receptor kinases
US11753406B2 (en) 2019-08-09 2023-09-12 Incyte Corporation Salts of a PD-1/PD-L1 inhibitor
MX2022003578A (es) 2019-09-30 2022-05-30 Incyte Corp Compuestos de pirido[3,2-d]pirimidina como inmunomoduladores.
BR112022009031A2 (pt) 2019-11-11 2022-10-11 Incyte Corp Sais e formas cristalinas de um inibidor de pd-1/pd-l1
CN116057045A (zh) 2020-06-05 2023-05-02 金耐特生物制药公司 成纤维细胞生长因子受体激酶抑制剂
TW202233615A (zh) 2020-11-06 2022-09-01 美商英塞特公司 Pd—1/pd—l1抑制劑之結晶形式
US11780836B2 (en) 2020-11-06 2023-10-10 Incyte Corporation Process of preparing a PD-1/PD-L1 inhibitor
MX2023005362A (es) 2020-11-06 2023-06-22 Incyte Corp Proceso para hacer un inhibidor de proteina de muerte programada 1 (pd-1)/ligando de muerte programada 1 (pd-l1) y sales y formas cristalinas del mismo.
CN117355533A (zh) * 2021-06-22 2024-01-05 株式会社Lg化学 作为蛋白激酶抑制剂的新型化合物
EP4268824A1 (en) * 2022-04-26 2023-11-01 Manros Therapeutics Imidazo[2,1-f][1,2,4]triazine derivatives useful as a medicament
WO2025199359A1 (en) * 2024-03-21 2025-09-25 The Translational Genomics Research Institute Methods of modulating cdk7 and flt3 using fused bicyclic compounds

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005082908A1 (en) 2004-02-25 2005-09-09 Schering Corporation Pyrazolotriazines as kinase inhibitors

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4166851A (en) 1977-05-16 1979-09-04 Merck & Co., Inc. Certain imidazo(1,2a)pyridine derivatives
CH635587A5 (fr) * 1978-01-09 1983-04-15 Aron Sa Derives amines de pyrazolo (1,5-a) s.triazine, therapeutiquement actifs et leurs procedes de preparation.
FR2619818B1 (fr) * 1987-09-01 1990-01-12 Sanofi Sa Imidazo (1,2-b) pyridazines, procede pour leur preparation et compositions pharmaceutiques les contenant
US5260285A (en) 1990-12-07 1993-11-09 Merck & Co., Inc. Substituted imidazopyridazines as angiotensin II antagonists
DE4327027A1 (de) 1993-02-15 1994-08-18 Bayer Ag Imidazoazine
CZ68199A3 (cs) 1996-08-28 1999-11-17 Pfizer Inc. 6,5-Heterobicyklické deriváty, farmaceutická kompozice na jejich bázi a způsob léčení chorob
CA2432417A1 (fr) * 2000-12-20 2002-06-27 Societe De Conseils De Recherches Et D'applications Scientifiques (S.C.R .A.S.) Inhibiteurs de kinases dependantes des cylines (cdk) et de la glycogene synthase kinase-3 (gsk-3)
FR2850653A1 (fr) * 2003-02-04 2004-08-06 Univ Pasteur Derives de pyrazolotriazine, procede de preparation et utilisations
MXPA05008955A (es) * 2003-02-28 2006-02-22 Teijin Pharma Ltd Derivados de pirazolo [1,5-a] pirimidina.
DE10356579A1 (de) * 2003-12-04 2005-07-07 Merck Patent Gmbh Aminderivate
US7537840B2 (en) * 2004-08-05 2009-05-26 H.B. Licensing & Financing, Inc. Polyamide adhesive and articles including the same
US7557103B2 (en) 2005-04-05 2009-07-07 Eli Lilly And Company Imidazopyridazine compounds

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005082908A1 (en) 2004-02-25 2005-09-09 Schering Corporation Pyrazolotriazines as kinase inhibitors

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