ES2552514T3 - Compuestos bicíclicos de piperazina - Google Patents

Compuestos bicíclicos de piperazina Download PDF

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ES2552514T3
ES2552514T3 ES12795138.2T ES12795138T ES2552514T3 ES 2552514 T3 ES2552514 T3 ES 2552514T3 ES 12795138 T ES12795138 T ES 12795138T ES 2552514 T3 ES2552514 T3 ES 2552514T3
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nhch3
och2ch2oh
och2ch3
och3
formula
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James John CRAWFORD
Daniel Fred Ortwine
Wendy B. Young
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F Hoffmann La Roche AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic 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
    • C07D487/04—Ortho-condensed systems
    • 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
    • A61K31/435—Heterocyclic 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
    • A61K31/4353—Heterocyclic 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
    • A61K31/437—Heterocyclic 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
    • 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
    • A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
    • 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
    • A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring systems
    • 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
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/5025—Pyridazines; Hydrogenated pyridazines ortho- or peri-condensed with heterocyclic ring systems
    • 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
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • 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
    • 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
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • 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
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic 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
    • C07D471/02—Heterocyclic 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
    • C07D471/04—Ortho-condensed systems
    • 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
    • C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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  • Neurology (AREA)
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  • Cardiology (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Biomedical Technology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Neurosurgery (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Communicable Diseases (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

Un compuesto, seleccionado de entre la Fórmula I: **Fórmula** ( Copiar figura 2 - Fórmula I - de la página 3) o estereómeros, tautómeros o sales farmacéuticamente aceptables de éstos, en donde, la lína continua / discontinua , indica un enlace individual o doble; X1, es CR1 ó N; X2, es CR2 ó N; X3, es CR3 ó N; en donde, ninguna, una, ó dos de entre las X1, X2 y X3, son N; Y1 e Y2, se seleccionan, de una forma independiente, entre CH y N; Y3, es C ó N; Y4, es CR6, N ó NH; en donde, una, ó dos de entre las Y1, Y2, Y3, e Y4, son N; R1, R2 y R3 , se seleccionan, de una forma independiente, de entre H, F, Cl, -NH2, -NHCH3, -N(CH3)2,-OH, -OCH3, -OCH2CH3, -OCH2CH2OH, y alquilo C1-C3 opcionalmente sustituido con F, Cl, CN, -NH2, -NHCH3, -N(CH3) , -OH, -OCH3, -OCH2CH3, y -OCH2CH2OH; R4, se selecciona de entre H, F, Cl, CN, -CH2OH, -CH(CH3)OH, -C(CH3)2OH,-CH(CF3)OH, -CH2F, -CHF2, -CH2CHF2, -CF3, -C(O)NH2, -C(O)NHCH3, -C(O)N(CH3)2, -NH2, -NHCH3, -N(CH3)2, -NHC(O)CH3, -OH, -OCH3, -OCH2CH3, -OCH2CH2OH, ciclopropilo, ciclopropilmetilo, 1-hidroxiciclopropilo, imidazolilo, pirazolilo, 3-hidroxi-oxetan- 3-ilo, oxetan-3-ilo, y azetidin-1-ilo; R5, se selecciona de entre -CH3, -CH2CH3, -CH2OH, -CH2F, -CHF2, -CF3, -CN, y -CH2CH2OH; ó dos grupos R5, forman un anillo carbocíclico o heterocíclico de 3, 4, 5, ó 6-miembros; ó un grupo R5 y un grupo R8, forman un anillo carbocíclico o heterocíclico de 3, 4, 5, ó 6-miembros; n, es 0, 1, 2, 3, ó 4; R6, se selecciona de entre H, Cl, -CH3, -CH2CH3, -CH2CH2OH, -CH2F, -CHF2, -CF3, -NH2, -NHCH3, -N(CH3)2, -OH, -OCH3, -OCH2CH3, y -OCH2CH2OH; R7, se selecciona de entre las estructuras:**Fórmula** en donde, la línea ondulada, indica el sitio de unión; R8, se selecciona de entre H, -CH3, -S(O)2CH3, ciclopropilo, azetidin-3-ilo, oxetan-3-ilo, y morfolin-4-ilo; Z, es CR9 ó N; en donde, R9, se selecciona de entre H, F, Cl, -CH3, -CH2CH3, -CH2CH2OH, -NH2, -NHCH3, -N(CH3)2, -OH, -OCH3, -OCH2CH3, y -OCH2CH2OH.
ES12795138.2T 2011-11-03 2012-11-02 Compuestos bicíclicos de piperazina Active ES2552514T3 (es)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201161555396P 2011-11-03 2011-11-03
US201161555396P 2011-11-03
PCT/US2012/063171 WO2013067260A1 (en) 2011-11-03 2012-11-02 Bicyclic piperazine compounds

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ES2552514T3 true ES2552514T3 (es) 2015-11-30

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US (1) US8722676B2 (es)
EP (1) EP2773640B1 (es)
JP (1) JP5808869B2 (es)
KR (1) KR20140096100A (es)
CN (1) CN104105697B (es)
BR (1) BR112014010391A2 (es)
CA (1) CA2852964A1 (es)
ES (1) ES2552514T3 (es)
HK (1) HK1201268A1 (es)
MX (1) MX2014005285A (es)
RU (1) RU2628616C2 (es)
WO (1) WO2013067260A1 (es)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5832664B2 (ja) * 2011-12-09 2015-12-16 エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ ブルトン型チロシンキナーゼの阻害剤
EP2813504A1 (en) * 2013-06-14 2014-12-17 Institut Quimic De Sarriá Cets, Fundació Privada 4-Amino-6-(2,6-dichlorophenyl)-2-(phenylamino)-pyrido[2,3-d]pyrimidin-7(8H)-one derivatives, synthesis and uses thereof
US9326985B2 (en) 2013-07-03 2016-05-03 Genentech, Inc. Heteroaryl pyridone and aza-pyridone amide compounds
CN103360399B (zh) * 2013-08-02 2016-03-02 北京大学 6-芳基取代-咪唑-[1,2-b]哒嗪类衍生物，其制备方法及用途
CN105793251B (zh) 2013-12-05 2018-10-12 豪夫迈·罗氏有限公司 具有亲电子官能性的杂芳基吡啶酮和氮杂-吡啶酮化合物
MX2016006351A (es) * 2013-12-13 2016-08-01 Hoffmann La Roche Inhibidores de tirosina cinasa de bruton.
MX2016011674A (es) 2014-03-12 2017-04-27 Novartis Ag Combinacion que comprende un inhibidor de btk y un inhibidor de akt.
WO2015157955A1 (en) 2014-04-17 2015-10-22 Abbvie Inc. Heterocyclic btk inhibit ors
WO2015177367A1 (en) 2014-05-23 2015-11-26 Active Biotech Ab Novel compounds useful as s100-inhibitors
JP6507234B2 (ja) 2014-10-02 2019-04-24 エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ ブルトンチロシンキナーゼ（ｂｔｋ）によって介入される障害の処置における使用のためのピラゾールカルボキサミド化合物
EP3212645B1 (en) 2014-10-27 2018-11-28 F.Hoffmann-La Roche Ag Process for making tricyclic lactam compounds
PL3267984T4 (pl) * 2015-03-10 2022-05-02 Aurigene Discovery Technologies Limited Związki 1,2,4-oksadiazolu i tiadiazolu jako immunomodulatory
CN104744463A (zh) * 2015-03-31 2015-07-01 山东友帮生化科技有限公司 6-氯-8-溴咪唑并[1,2-a]吡啶的合成方法
FR3037959B1 (fr) * 2015-06-23 2017-08-04 Servier Lab Nouveaux derives bicycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
US20190256499A1 (en) 2016-11-08 2019-08-22 Merck Patent Gmbh Substituted quinoxaline derivatives as inhibitors of pfkfb
AR110282A1 (es) 2016-12-02 2019-03-13 Hoffmann La Roche Compuestos de amida bicíclica y uso de éstos en el tratamiento de enfermedades mediadas por rip1
JP6800334B2 (ja) * 2016-12-15 2020-12-16 エフ．ホフマン−ラ ロシュ アーゲーＦ． Ｈｏｆｆｍａｎｎ−Ｌａ Ｒｏｃｈｅ Ａｋｔｉｅｎｇｅｓｅｌｌｓｃｈａｆｔ Ｂｔｋ阻害剤を調製するプロセス
EP3564232B1 (en) 2016-12-27 2022-01-26 Riken Bmp-signal-inhibiting compound
CN109206435B (zh) * 2017-06-29 2020-09-08 中国医药研究开发中心有限公司 噻吩并[3,2-d]嘧啶类化合物及其制备方法和医药用途
KR20240065201A (ko) 2017-07-14 2024-05-14 에프. 호프만-라 로슈 아게 이환형 케톤 화합물 및 이의 사용 방법
BR112020008446A2 (pt) 2017-10-31 2020-12-29 F. Hoffmann-La Roche Ag Sulfonas e sulfóxidos bicíclicos e seus métodos de uso
CN110256446B (zh) * 2018-08-01 2021-12-14 上海海雁医药科技有限公司 苯并杂环取代的环戊二烯并[4,5]吡咯并吡嗪-1-酮衍生物及其应用
CA3131517A1 (en) 2019-02-25 2020-09-03 Guangzhou Lupeng Pharmaceutical Company Ltd. Inhibitor of btk and mutants thereof
WO2021066958A1 (en) 2019-10-05 2021-04-08 Newave Pharmaceutical Inc. Inhibitor of btk and mutants thereof
AU2021222197A1 (en) * 2020-02-20 2022-09-08 Hutchison Medipharma Limited Heteroaryl heterocyclic compounds and uses thereof
WO2021219071A1 (en) * 2020-04-30 2021-11-04 Beigene (Beijing) Co., Ltd. Process for preparing protac btk degraders
CN115715291A (zh) * 2020-06-18 2023-02-24 上海华汇拓医药科技有限公司 布鲁顿酪氨酸激酶抑制剂及其制备方法
PE20232044A1 (es) * 2020-09-21 2023-12-27 Hutchison Medipharma Ltd Compuestos heterociclicos de heteroarilo y usos de los mismos
WO2022094172A2 (en) 2020-10-30 2022-05-05 Newave Pharmaceutical Inc. Inhibitors of btk
JP7490548B2 (ja) 2020-12-14 2024-05-27 住友化学株式会社 高分子化合物の製造方法
AU2021401056A1 (en) 2020-12-20 2023-08-03 Guangzhou Lupeng Pharmaceutical Company Ltd. Btk degrader
WO2023143491A1 (zh) * 2022-01-28 2023-08-03 和记黄埔医药（上海）有限公司 7,8-二氢-2h-环戊二烯并吡咯并吡嗪酮化合物的合成方法

Family Cites Families (38)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3773919A (en) 1969-10-23 1973-11-20 Du Pont Polylactide-drug mixtures
US5583024A (en) 1985-12-02 1996-12-10 The Regents Of The University Of California Recombinant expression of Coleoptera luciferase
DE4224133A1 (de) * 1992-07-22 1994-01-27 Thomae Gmbh Dr K Benzimidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung
US5543523A (en) 1994-11-15 1996-08-06 Regents Of The University Of Minnesota Method and intermediates for the synthesis of korupensamines
JPH08336393A (ja) 1995-04-13 1996-12-24 Mitsubishi Chem Corp 光学活性なγ−置換−β−ヒドロキシ酪酸エステルの製造法
US6602677B1 (en) 1997-09-19 2003-08-05 Promega Corporation Thermostable luciferases and methods of production
EP1409125B1 (en) 2001-07-12 2016-04-20 Reaxa Limited Microencapsulated catalyst, methods of preparation and methods of use thereof
US6514989B1 (en) * 2001-07-20 2003-02-04 Hoffmann-La Roche Inc. Aromatic and heteroaromatic substituted 1,2,4-triazolo pyridine derivatives
US7405295B2 (en) 2003-06-04 2008-07-29 Cgi Pharmaceuticals, Inc. Certain imidazo[1,2-a]pyrazin-8-ylamines and method of inhibition of Bruton's tyrosine kinase by such compounds
US7393848B2 (en) 2003-06-30 2008-07-01 Cgi Pharmaceuticals, Inc. Certain heterocyclic substituted imidazo[1,2-A]pyrazin-8-ylamines and methods of inhibition of Bruton's tyrosine kinase by such compounds
US20060178367A1 (en) 2004-11-10 2006-08-10 Currie Kevin S Certain imidazo[1,2-a]pyrazin-8-ylamines, method of making, and method of use thereof
KR101357524B1 (ko) 2005-03-10 2014-02-03 질레드 코네티컷 인코포레이티드 특정 치환된 아미드, 그의 제조 방법, 및 사용 방법
CN109053523B (zh) 2005-10-07 2022-03-25 埃克塞利希斯股份有限公司 作为用于治疗增生性疾病的mek抑制剂的吖丁啶
US7838523B2 (en) 2006-09-11 2010-11-23 Cgi Pharmaceuticals, Inc. Certain substituted amides, method of making, and method of use thereof
PE20080839A1 (es) 2006-09-11 2008-08-23 Cgi Pharmaceuticals Inc Determinadas amidas sustituidas, metodo de elaboracion y metodo de uso de las mismas
AR063946A1 (es) 2006-09-11 2009-03-04 Cgi Pharmaceuticals Inc Determinadas pirimidinas sustituidas, el uso de las mismas para el tratamiento de enfermedades mediadas por la inhibicion de la actividad de btk y composiciones farmaceuticas que las comprenden.
PT2530083T (pt) * 2006-09-22 2016-08-01 Pharmacyclics Llc Inibidores de tirosina cinase de bruton
CL2008002793A1 (es) 2007-09-20 2009-09-04 Cgi Pharmaceuticals Inc Compuestos derivados de amidas sustituidas, inhibidores de la actividad de btk; composicion farmaceutica que los comprende; utiles en el tratamiento del cancer, trastornos oseos, enfermedades autoinmunes, entre otras
CA2708361C (en) * 2007-12-14 2016-06-07 F. Hoffmann-La Roche Ag Novel imidazo[1,2-a]pyridine and imidazo[1,2-b]pyridazine derivatives
US8426441B2 (en) 2007-12-14 2013-04-23 Roche Palo Alto Llc Inhibitors of bruton's tyrosine kinase
US7683064B2 (en) 2008-02-05 2010-03-23 Roche Palo Alto Llc Inhibitors of Bruton's tyrosine kinase
AU2009244291B2 (en) * 2008-05-06 2014-02-13 Genentech, Inc. Substituted amides, method of making, and use as Btk inhibitors
KR101299867B1 (ko) 2008-06-24 2013-08-23 에프. 호프만-라 로슈 아게 신규한 치환 피리딘-2-온 및 피리다진-3-온
WO2010000633A1 (en) 2008-07-02 2010-01-07 F. Hoffmann-La Roche Ag Novel phenylpyrazinones as kinase inhibitors
CN102066370B (zh) 2008-07-15 2014-05-14 霍夫曼-拉罗奇有限公司 苯基-咪唑并吡啶类和哒嗪类
ES2461494T3 (es) * 2008-07-18 2014-05-20 F. Hoffmann-La Roche Ag Nuevas fenilimidazopirazinas
WO2010011837A1 (en) * 2008-07-24 2010-01-28 Bristol-Myers Squibb Company Fused heterocyclic compounds useful as kinase modulators
US8598174B2 (en) 2008-11-12 2013-12-03 Genetech, Inc. Pyridazinones, method of making, and method of use thereof
WO2010068810A2 (en) * 2008-12-10 2010-06-17 Cgi Pharmaceuticals, Inc. Certain substituted amides, method of making, and method of use thereof
US8765754B2 (en) * 2009-04-29 2014-07-01 Locus Pharmaceuticals, Inc. Pyrrolotriazine compounds
WO2011029046A1 (en) * 2009-09-04 2011-03-10 Biogen Idec Ma Inc. Bruton's tyrosine kinase inhibitors
PT2545052E (pt) * 2010-03-11 2015-02-18 Gilead Connecticut Inc Inibidores da syk à base de imidazopiridinas
US8618107B2 (en) 2010-05-07 2013-12-31 Gilead Connecticut, Inc. Pyridone and aza-pyridone compounds and methods of use
AR082590A1 (es) 2010-08-12 2012-12-19 Hoffmann La Roche Inhibidores de la tirosina-quinasa de bruton
CA2809662C (en) 2010-09-01 2019-04-16 Gilead Connecticut, Inc. Pyridazinones, method of making, and method of use thereof
CA2809836C (en) 2010-09-01 2019-01-15 Gilead Connecticut, Inc. Pyridinones/pyrazinones, method of making, and method of use thereof for the treatment of disorders mediated by bruton's tyrosine kinase
EP2709997B1 (en) 2011-05-17 2016-06-29 F.Hoffmann-La Roche Ag Inhibitors of bruton's tyrosine kinase
BR112014003582A2 (pt) 2011-08-17 2017-03-14 Hoffmann La Roche inibidores da tirosina quinase de bruton

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US8722676B2 (en) 2014-05-13
JP5808869B2 (ja) 2015-11-10
US20130116262A1 (en) 2013-05-09
CN104105697B (zh) 2016-11-09
EP2773640B1 (en) 2015-08-19
EP2773640A1 (en) 2014-09-10
RU2014121073A (ru) 2015-12-10
CA2852964A1 (en) 2013-05-10
CN104105697A (zh) 2014-10-15
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JP2014532715A (ja) 2014-12-08
MX2014005285A (es) 2014-05-30

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