TWI648272B - 經取代之四氫咔唑及咔唑甲醯胺化合物 - Google Patents

經取代之四氫咔唑及咔唑甲醯胺化合物 Download PDF

Info

Publication number
TWI648272B
TWI648272B TW103121681A TW103121681A TWI648272B TW I648272 B TWI648272 B TW I648272B TW 103121681 A TW103121681 A TW 103121681A TW 103121681 A TW103121681 A TW 103121681A TW I648272 B TWI648272 B TW I648272B
Authority
TW
Taiwan
Prior art keywords
compound
formula
mmol
bromo
mixture
Prior art date
Application number
TW103121681A
Other languages
English (en)
Chinese (zh)
Other versions
TW201536774A (zh
Inventor
約瑟夫Ａ 提諾
Joseph A. Tino
亞奴拉格Ｓ 斯里瓦斯塔瓦
Anurag S. Srivastava
壽成 高
Soo Sung Ko
麥克Ａ 嘉利拉
Michael A. Galella
查理斯Ｍ 蘭吉芬
Charles M. Langevine
喬治 德魯卡
George Delucca
劉慶杰
Qingjie Liu
道格拉斯Ａ 巴特
Douglas A. BATT
史考特 杭特 瓦特森
Scott Hunter Watterson
清 石
Qing Shi
麥拉 包多恩 伯坦德
Myra Beaudoin BERTRAND
Original Assignee
美商必治妥美雅史谷比公司
Bristol-Myers Squibb Company
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 美商必治妥美雅史谷比公司, Bristol-Myers Squibb Company filed Critical 美商必治妥美雅史谷比公司
Publication of TW201536774A publication Critical patent/TW201536774A/zh
Application granted granted Critical
Publication of TWI648272B publication Critical patent/TWI648272B/zh

Links

Classifications

    • 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
    • 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
    • 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
    • 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
    • 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
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Rheumatology (AREA)
  • Neurosurgery (AREA)
  • Epidemiology (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Hospice & Palliative Care (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Transplantation (AREA)
  • Psychiatry (AREA)
  • Pain & Pain Management (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Indole Compounds (AREA)
TW103121681A 2013-06-25 2014-06-24 經取代之四氫咔唑及咔唑甲醯胺化合物 TWI648272B (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US201361839141P 2013-06-25 2013-06-25
US61/839,141 2013-06-25

Publications (2)

Publication Number Publication Date
TW201536774A TW201536774A (zh) 2015-10-01
TWI648272B true TWI648272B (zh) 2019-01-21

Family

ID=51210830

Family Applications (1)

Application Number Title Priority Date Filing Date
TW103121681A TWI648272B (zh) 2013-06-25 2014-06-24 經取代之四氫咔唑及咔唑甲醯胺化合物

Country Status (31)

Country Link
US (6) US9334290B2 (en:Method)
EP (1) EP3013814B1 (en:Method)
JP (1) JP6353529B2 (en:Method)
KR (1) KR102346508B1 (en:Method)
CN (1) CN105358546B (en:Method)
AR (1) AR096721A1 (en:Method)
AU (1) AU2014302548B2 (en:Method)
BR (1) BR112015030723A8 (en:Method)
CA (1) CA2916500A1 (en:Method)
CL (1) CL2015003635A1 (en:Method)
CY (1) CY1119371T1 (en:Method)
DK (1) DK3013814T3 (en:Method)
EA (1) EA026729B1 (en:Method)
ES (1) ES2636652T3 (en:Method)
HR (1) HRP20171031T1 (en:Method)
HU (1) HUE034460T2 (en:Method)
IL (1) IL243296B (en:Method)
LT (1) LT3013814T (en:Method)
MA (1) MA38648B1 (en:Method)
MY (1) MY176631A (en:Method)
PE (1) PE20160519A1 (en:Method)
PH (1) PH12015502630A1 (en:Method)
PL (1) PL3013814T3 (en:Method)
PT (1) PT3013814T (en:Method)
RS (1) RS56371B1 (en:Method)
SI (1) SI3013814T1 (en:Method)
SM (1) SMT201700422T1 (en:Method)
TN (1) TN2015000529A1 (en:Method)
TW (1) TWI648272B (en:Method)
UY (1) UY35625A (en:Method)
WO (1) WO2014210085A1 (en:Method)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014210087A1 (en) 2013-06-25 2014-12-31 Bristol-Myers Squibb Company Carbazole carboxamide compounds useful as kinase inhibitors
LT3209651T (lt) * 2014-10-24 2020-01-10 Bristol-Myers Squibb Company Karbazolo dariniai
JP6592512B2 (ja) 2014-10-24 2019-10-16 ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ 三環式アトロプ異性体の化合物
LT3461821T (lt) 2014-10-24 2020-08-10 Bristol-Myers Squibb Company Indolo karboksamido junginiai, naudotini kaip kinazės inhibitoriai
US10842963B2 (en) 2016-07-01 2020-11-24 Brio Device, LLC Intubation stylet with video feed
CN108101905A (zh) * 2016-11-24 2018-06-01 中国科学院上海药物研究所 嘧啶并[5,4-b]吲嗪或嘧啶并[5,4-b]吡呤化合物、其制备方法及用途
US11590167B2 (en) 2016-12-03 2023-02-28 Juno Therapeutic, Inc. Methods and compositions for use of therapeutic T cells in combination with kinase inhibitors
US10875843B2 (en) 2016-12-20 2020-12-29 Bristol-Myers Squibb Company Process for preparing tetrahydrocarbazole carboxamide compound
EP3789040A4 (en) 2018-04-27 2022-03-09 ONO Pharmaceutical Co., Ltd. PREVENTIVE AND/OR THERAPEUTIC AGENT FOR AUTOIMMUNE DISEASES WITH A COMPOUND WITH BTK INHIBITING ACTIVITY AS AN INGREDIENT
CA3224985C (en) 2018-07-31 2025-11-18 Loxo Oncology, Inc. SPRAY-DRIED DISPERSIONS, FORMULATIONS AND POLYMORPHIES OF (S)-5-AMINO-3-(4-((5-FLUORO-2-METHOXYBENZAMIDO)METHYL)PHENYL)(1,1,1-TRIFLUOROPROPANE-2-YL)-1H-PYRAZOLE-4-CARBOXAMIDE
WO2022140246A1 (en) 2020-12-21 2022-06-30 Hangzhou Jijing Pharmaceutical Technology Limited Methods and compounds for targeted autophagy
US20240216330A1 (en) 2021-04-02 2024-07-04 Biogen Ma Inc. Combination treatment methods of multiple sclerosis
AU2023220628A1 (en) * 2022-02-15 2024-05-23 F. Hoffmann-La Roche Ag Processes for the preparation of 1,2,3,5,6,7-hexahydro-s-indacene derivatives

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011159857A1 (en) * 2010-06-16 2011-12-22 Bristol-Myers Squibb Company Carboline carboxamide compounds useful as kinase inhibitors
US8084620B2 (en) * 2008-12-19 2011-12-27 Bristol-Myers Squibb Company Carbazole carboxamide compounds useful as kinase inhibitors

Family Cites Families (27)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4200750A (en) 1977-01-07 1980-04-29 Westwood Pharmaceuticals Inc. 4-Substituted imidazo [1,2-a]quinoxalines
CA2140722A1 (en) 1994-01-24 1995-07-25 Joseph A. Jakubowski Beta-carboline thromboxane synthase inhibitors
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
WO2005047290A2 (en) 2003-11-11 2005-05-26 Cellular Genomics Inc. Imidazo[1,2-a] pyrazin-8-ylamines as kinase inhibitors
US7713973B2 (en) 2004-10-15 2010-05-11 Takeda Pharmaceutical Company Limited Kinase inhibitors
CA2587192A1 (en) 2004-11-10 2006-05-18 Cgi Pharmaceuticals, Inc. Imidazo[1 , 2-a] pyrazin-8-ylamines useful as modulators of kinase activity
AP2334A (en) 2004-12-17 2011-12-06 Glenmark Pharmaceuticals Sa Novel heterocyclic compounds useful for the treatment of inflamatory and allergic disorders.
US7947835B2 (en) 2005-03-10 2011-05-24 Cgi Pharmaceuticals, Inc. Certain substituted amides, method of making, and method of use thereof
JP2009508872A (ja) 2005-09-16 2009-03-05 セレネックス， インコーポレイテッド カルバゾール誘導体
US20070078136A1 (en) 2005-09-22 2007-04-05 Bristol-Myers Squibb Company Fused heterocyclic compounds useful as kinase modulators
US7723336B2 (en) 2005-09-22 2010-05-25 Bristol-Myers Squibb Company Fused heterocyclic compounds useful as kinase modulators
US8518964B2 (en) 2005-11-22 2013-08-27 Merck Sharp & Dohme Corp. Tricyclic compounds useful as inhibitors of kinases
CA2663178C (en) 2006-09-11 2016-01-12 Matrix Laboratories Ltd. Dibenzofuran derivatives as inhibitors of pde-4 and pde-10
WO2008033858A2 (en) 2006-09-11 2008-03-20 Cgi Pharmaceuticals, Inc. Kinase inhibitors, and methods of using and identifying kinase inhibitors
US20090062251A1 (en) 2007-08-17 2009-03-05 Astrazeneca Ab Novel Compounds 002
EP2231143B1 (en) 2007-12-13 2013-07-03 Merck Sharp & Dohme Corp. 5H-pyrido[4,3-b]indoles as INHIBITORS OF JANUS KINASES
FI2247558T4 (fi) 2008-02-14 2024-09-19 Lilly Co Eli Uusia kuvantamisaineita neurologisen toimintahäiriön toteamiseen
GB0809360D0 (en) 2008-05-22 2008-07-02 Isis Innovation Calcium modulation
EP2151441A1 (en) 2008-08-06 2010-02-10 Julius-Maximilians-Universität Würzburg Beta-carbolin-derivates as substrates for an enzyme
CN101475571B (zh) 2009-01-21 2011-06-22 中国药科大学 β-咔啉类细胞周期蛋白依赖性激酶2抑制剂及其用途
US8242260B2 (en) 2009-08-28 2012-08-14 Novartis Ag Compounds and compositions as protein kinase inhibitors
US9029387B2 (en) 2010-03-26 2015-05-12 Merck Patent Gmbh Benzonaphthyridinamines as autotaxin inhibitors
EP2455378A1 (en) 2010-11-03 2012-05-23 Philip Morris Products S.A. Carbazole and carboline derivatives, and preparation and therapeutic applications thereof
CA2817896A1 (en) 2010-11-15 2012-05-24 Viiv Healthcare Uk Limited Inhibitors of hiv replication
ES2590491T3 (es) 2011-05-17 2016-11-22 F. Hoffmann-La Roche Ag Inhibidores de la tirosina quinasa de Bruton
WO2013054185A1 (en) 2011-10-13 2013-04-18 Pfizer, Inc. Pyrimidine and pyridine derivatives useful in therapy

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8084620B2 (en) * 2008-12-19 2011-12-27 Bristol-Myers Squibb Company Carbazole carboxamide compounds useful as kinase inhibitors
WO2011159857A1 (en) * 2010-06-16 2011-12-22 Bristol-Myers Squibb Company Carboline carboxamide compounds useful as kinase inhibitors

Also Published As

Publication number Publication date
UY35625A (es) 2014-12-31
US9334290B2 (en) 2016-05-10
TW201536774A (zh) 2015-10-01
EA026729B1 (ru) 2017-05-31
BR112015030723A8 (pt) 2020-01-07
AU2014302548A1 (en) 2016-02-11
PE20160519A1 (es) 2016-05-21
PT3013814T (pt) 2017-08-10
US20170283438A1 (en) 2017-10-05
CN105358546A (zh) 2016-02-24
RS56371B1 (sr) 2017-12-29
US10106559B2 (en) 2018-10-23
CY1119371T1 (el) 2018-02-14
MA38648A1 (fr) 2017-09-29
ES2636652T3 (es) 2017-10-06
AR096721A1 (es) 2016-01-27
HRP20171031T1 (hr) 2017-10-06
US20190023719A1 (en) 2019-01-24
US20160194338A1 (en) 2016-07-07
SMT201700422T1 (it) 2017-11-15
MA38648B1 (fr) 2018-06-29
US20180079758A1 (en) 2018-03-22
US9850258B2 (en) 2017-12-26
BR112015030723A2 (pt) 2017-07-25
CN105358546B (zh) 2017-10-31
US20140378475A1 (en) 2014-12-25
WO2014210085A1 (en) 2014-12-31
EP3013814B1 (en) 2017-06-14
SI3013814T1 (sl) 2017-08-31
MY176631A (en) 2020-08-19
WO2014210085A9 (en) 2015-12-23
CA2916500A1 (en) 2014-12-31
TN2015000529A1 (en) 2017-04-06
JP6353529B2 (ja) 2018-07-04
KR20160022889A (ko) 2016-03-02
KR102346508B1 (ko) 2022-01-03
HUE034460T2 (en) 2018-02-28
US20190382416A1 (en) 2019-12-19
PH12015502630A1 (en) 2016-03-07
EA201592287A1 (ru) 2016-06-30
AU2014302548B2 (en) 2018-05-10
JP2016523907A (ja) 2016-08-12
IL243296B (en) 2018-05-31
EP3013814A1 (en) 2016-05-04
US10435415B2 (en) 2019-10-08
CL2015003635A1 (es) 2016-07-29
HK1223359A1 (en) 2017-07-28
PL3013814T3 (pl) 2017-11-30
DK3013814T3 (en) 2017-09-25
LT3013814T (lt) 2017-08-10

Similar Documents

Publication Publication Date Title
TWI648272B (zh) 經取代之四氫咔唑及咔唑甲醯胺化合物
CN105473573B (zh) 用作激酶抑制剂的咔唑甲酰胺化合物
TWI620737B (zh) 作爲ＩＬ－１２、ＩＬ－２３及／或ＩＦＮα反應調節劑之經烷基－醯胺取代之吡啶化合物
CN107108583A (zh) 可用作激酶抑制剂的吲哚甲酰胺化合物
JP6531167B2 (ja) ブロモドメイン阻害剤としてのテトラヒドロキノリン誘導体
HK1223359B (en) Substituted tetrahydrocarbazole and carbazole carboxamide compounds useful as kinase inhibitors

Legal Events

Date Code Title Description
MM4A Annulment or lapse of patent due to non-payment of fees