CN109456272A - Mek抑制剂的制备和包含mek抑制剂的制剂 - Google Patents

Mek抑制剂的制备和包含mek抑制剂的制剂 Download PDF

Info

Publication number
CN109456272A
CN109456272A CN201810684986.7A CN201810684986A CN109456272A CN 109456272 A CN109456272 A CN 109456272A CN 201810684986 A CN201810684986 A CN 201810684986A CN 109456272 A CN109456272 A CN 109456272A
Authority
CN
China
Prior art keywords
compound
formula
solution
methyl
bromo
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.)
Pending
Application number
CN201810684986.7A
Other languages
English (en)
Chinese (zh)
Inventor
C.M.克雷尔
M.米森
D.A.尼德尔
W.H.帕钦格
M-c.沃尔夫
D.齐默尔曼
W.刘
P.J.斯滕格尔
P.尼科尔斯
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.)
Array Biopharma Inc
Original Assignee
Array Biopharma Inc
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=50488781&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CN109456272(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Array Biopharma Inc filed Critical Array Biopharma Inc
Publication of CN109456272A publication Critical patent/CN109456272A/zh
Pending legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/41Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/41641,3-Diazoles
    • A61K31/41841,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/08Radicals containing only hydrogen and carbon atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/02Inorganic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/12Carboxylic acids; Salts or anhydrides thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/30Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
    • A61K47/36Polysaccharides; Derivatives thereof, e.g. gums, starch, alginate, dextrin, hyaluronic acid, chitosan, inulin, agar or pectin
    • A61K47/38Cellulose; Derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/0012Galenical forms characterised by the site of application
    • A61K9/0053Mouth and digestive tract, i.e. intraoral and peroral administration
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2009Inorganic compounds
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2013Organic compounds, e.g. phospholipids, fats
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2013Organic compounds, e.g. phospholipids, fats
    • A61K9/2018Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/20Pills, tablets, discs, rods
    • A61K9/2004Excipients; Inactive ingredients
    • A61K9/2022Organic macromolecular compounds
    • A61K9/205Polysaccharides, e.g. alginate, gums; Cyclodextrin
    • A61K9/2054Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D235/00Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • CCHEMISTRY; METALLURGY
    • C30CRYSTAL GROWTH
    • C30BSINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
    • C30B29/00Single crystals or homogeneous polycrystalline material with defined structure characterised by the material or by their shape
    • C30B29/54Organic compounds
    • CCHEMISTRY; METALLURGY
    • C30CRYSTAL GROWTH
    • C30BSINGLE-CRYSTAL GROWTH; UNIDIRECTIONAL SOLIDIFICATION OF EUTECTIC MATERIAL OR UNIDIRECTIONAL DEMIXING OF EUTECTOID MATERIAL; REFINING BY ZONE-MELTING OF MATERIAL; PRODUCTION OF A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; SINGLE CRYSTALS OR HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; AFTER-TREATMENT OF SINGLE CRYSTALS OR A HOMOGENEOUS POLYCRYSTALLINE MATERIAL WITH DEFINED STRUCTURE; APPARATUS THEREFOR
    • C30B7/00Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions
    • C30B7/08Single-crystal growth from solutions using solvents which are liquid at normal temperature, e.g. aqueous solutions by cooling of the solution
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07BGENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13Crystalline forms, e.g. polymorphs

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Molecular Biology (AREA)
  • Engineering & Computer Science (AREA)
  • Biophysics (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Metallurgy (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Materials Engineering (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Biochemistry (AREA)
  • Nutrition Science (AREA)
  • Physiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CN201810684986.7A 2012-10-19 2013-10-18 Mek抑制剂的制备和包含mek抑制剂的制剂 Pending CN109456272A (zh)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201261716169P 2012-10-19 2012-10-19
US61/716,169 2012-10-19
CN201380063271.5A CN104870427B (zh) 2012-10-19 2013-10-18 Mek抑制剂的制备和包含mek抑制剂的制剂

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
CN201380063271.5A Division CN104870427B (zh) 2012-10-19 2013-10-18 Mek抑制剂的制备和包含mek抑制剂的制剂

Publications (1)

Publication Number Publication Date
CN109456272A true CN109456272A (zh) 2019-03-12

Family

ID=50488781

Family Applications (3)

Application Number Title Priority Date Filing Date
CN201380063271.5A Active CN104870427B (zh) 2012-10-19 2013-10-18 Mek抑制剂的制备和包含mek抑制剂的制剂
CN201810684986.7A Pending CN109456272A (zh) 2012-10-19 2013-10-18 Mek抑制剂的制备和包含mek抑制剂的制剂
CN201811124073.6A Active CN109336824B (zh) 2012-10-19 2013-10-18 Mek抑制剂的制备和包含mek抑制剂的制剂

Family Applications Before (1)

Application Number Title Priority Date Filing Date
CN201380063271.5A Active CN104870427B (zh) 2012-10-19 2013-10-18 Mek抑制剂的制备和包含mek抑制剂的制剂

Family Applications After (1)

Application Number Title Priority Date Filing Date
CN201811124073.6A Active CN109336824B (zh) 2012-10-19 2013-10-18 Mek抑制剂的制备和包含mek抑制剂的制剂

Country Status (23)

Country Link
US (7) US9238627B2 (enExample)
EP (3) EP2909182B1 (enExample)
JP (3) JP6385939B2 (enExample)
CN (3) CN104870427B (enExample)
AR (1) AR099630A1 (enExample)
BR (1) BR112015008623B1 (enExample)
CA (2) CA2888474C (enExample)
CY (1) CY1122670T1 (enExample)
DK (2) DK2909182T3 (enExample)
ES (2) ES2971077T3 (enExample)
FI (1) FI3702351T3 (enExample)
HR (1) HRP20240033T1 (enExample)
HU (2) HUE047708T2 (enExample)
JO (1) JOP20130304B1 (enExample)
LT (1) LT3702351T (enExample)
PL (2) PL3702351T3 (enExample)
PT (2) PT2909182T (enExample)
RS (1) RS65117B1 (enExample)
RU (2) RU2018127873A (enExample)
SI (2) SI2909182T1 (enExample)
SM (1) SMT202400044T1 (enExample)
TW (1) TWI650316B (enExample)
WO (1) WO2014063024A1 (enExample)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR099630A1 (es) 2012-10-19 2016-08-10 Novartis Ag Preparación de un inhibidor de mek y formulación que lo comprende
CN105566225A (zh) * 2015-02-16 2016-05-11 苏州晶云药物科技有限公司 一种口服丝裂原活化蛋白激酶抑制剂的晶型及其制备方法
MX387795B (es) * 2016-06-03 2025-03-19 Array Biopharma Inc Combinaciones farmaceuticas.
CN109438362B (zh) 2017-11-14 2020-07-21 深圳市塔吉瑞生物医药有限公司 一种取代的苯并咪唑化合物及包含该化合物的组合物
TW201938165A (zh) 2017-12-18 2019-10-01 美商輝瑞股份有限公司 治療癌症的方法及組合療法
US11395823B2 (en) * 2018-01-09 2022-07-26 Duke University Topical administration of MEK inhibiting agents for the treatment of skin disorders
WO2020212832A1 (en) * 2019-04-16 2020-10-22 Alembic Pharmaceuticals Limited Process of preparation of benzimidazole compounds
WO2021116901A1 (en) * 2019-12-09 2021-06-17 Biocon Limited Forms of binimetinib and process for preparation thereof
EP4225307A1 (en) 2020-10-05 2023-08-16 Pierre Fabre Medicament Combination of encorafenib and binimetinib as adjuvant treatment for resected stage ii melanoma
CN112679438A (zh) * 2020-12-31 2021-04-20 武汉九州钰民医药科技有限公司 制备司美替尼的方法
WO2022251193A1 (en) 2021-05-27 2022-12-01 Mirati Therapeutics, Inc. Combination therapies
WO2023084489A1 (en) 2021-11-15 2023-05-19 Pfizer Inc. Methods of treating coronavirus disease 2019
EP4460303A4 (en) * 2022-01-06 2025-07-23 Msn Laboratories Private Ltd R&D Center IMPROVED PROCESS FOR THE PREPARATION OF 5-[(4-BROMO-2-FLUOROPHENYL)AMINO]-4-FLUORO-N-(2HYDROXYETHOXY)-1-METHYL-1H-BENZIMIDAZOLE-6-CARBOXAMIDE
WO2024003942A1 (en) * 2022-07-01 2024-01-04 Natco Pharma Limited An improved process for the preparation of selumetinib sulfate
TW202508595A (zh) 2023-05-04 2025-03-01 美商銳新醫藥公司 用於ras相關疾病或病症之組合療法
WO2025034702A1 (en) 2023-08-07 2025-02-13 Revolution Medicines, Inc. Rmc-6291 for use in the treatment of ras protein-related disease or disorder
WO2025080946A2 (en) 2023-10-12 2025-04-17 Revolution Medicines, Inc. Ras inhibitors
WO2025171296A1 (en) 2024-02-09 2025-08-14 Revolution Medicines, Inc. Ras inhibitors
FR3159741A1 (fr) 2024-03-04 2025-09-05 Pierre Fabre Medicament Formulation topique comprenant du binimetinib
WO2025240847A1 (en) 2024-05-17 2025-11-20 Revolution Medicines, Inc. Ras inhibitors

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1652776A (zh) * 2002-03-13 2005-08-10 阵列生物制药公司 作为mek抑制剂的n3烷基化苯并咪唑衍生物

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL144214A0 (en) * 1999-01-13 2002-05-23 Warner Lambert Co Benzoheterocycles and their use as mek inhibitors
CN1358094A (zh) * 1999-07-16 2002-07-10 沃尼尔·朗伯公司 用mek抑制剂治疗慢性疼痛的方法
US7235537B2 (en) * 2002-03-13 2007-06-26 Array Biopharma, Inc. N3 alkylated benzimidazole derivatives as MEK inhibitors
WO2005009975A2 (en) * 2003-07-24 2005-02-03 Warner-Lambert Company Llc Benzimidazole derivatives as mek inhibitors
WO2006030826A1 (ja) 2004-09-17 2006-03-23 Eisai R & D Management Co., Ltd. 医薬組成物
ES2567133T3 (es) 2005-06-23 2016-04-20 Array Biopharma, Inc. Proceso para preparar compuestos de benzoimidazol
BRPI0612306A2 (pt) 2005-06-23 2010-11-03 Array Biopharma Inc processo snar para preparar composto de benzimidazol
TWI405756B (zh) * 2005-12-21 2013-08-21 Array Biopharma Inc 新穎硫酸氫鹽
CN101341132A (zh) * 2005-12-21 2009-01-07 阿斯利康(瑞典)有限公司 作为mek抑制剂用于治疗癌症的6-(4-溴-2-氯-苯基氨基)-7-氟-n-(2-羟基乙氧基)-3-甲基-3h-苯并咪唑-5-甲酰胺的甲苯磺酸盐
KR20150091434A (ko) * 2007-07-30 2015-08-10 아디아 바이오사이언스즈 인크. 다형체를 포함하는, mek의 억제제로서의 n-(아릴아미노) 술폰아미드의 유도체 및 조성물, 사용 방법 및 이의 제조 방법
WO2009064675A1 (en) 2007-11-12 2009-05-22 Takeda Pharmaceutical Company Limited Mapk/erk kinase inhibitors
JP2012524114A (ja) * 2009-04-21 2012-10-11 ノバルティス アーゲー Mek阻害剤としてのヘテロ環式化合物
WO2012145503A1 (en) 2011-04-21 2012-10-26 Novartis Ag Pharmaceutical combinations
EP2750672A1 (en) 2011-09-01 2014-07-09 Novartis AG Use of organic compound for the treatment of noonan syndrome
AR099630A1 (es) 2012-10-19 2016-08-10 Novartis Ag Preparación de un inhibidor de mek y formulación que lo comprende

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1652776A (zh) * 2002-03-13 2005-08-10 阵列生物制药公司 作为mek抑制剂的n3烷基化苯并咪唑衍生物

Also Published As

Publication number Publication date
HUE047708T2 (hu) 2020-05-28
US20180296533A1 (en) 2018-10-18
EP3702351A1 (en) 2020-09-02
HRP20240033T1 (hr) 2024-03-29
EP2909182A4 (en) 2016-07-06
EP2909182B1 (en) 2019-12-04
US20160168103A1 (en) 2016-06-16
US9562016B2 (en) 2017-02-07
PL3702351T3 (pl) 2024-04-02
CN109336824A (zh) 2019-02-15
CN104870427A (zh) 2015-08-26
TWI650316B (zh) 2019-02-11
JP6385939B2 (ja) 2018-09-05
EP3702351B1 (en) 2023-11-22
PT2909182T (pt) 2020-03-02
JP2016503391A (ja) 2016-02-04
JOP20130304B1 (ar) 2021-08-17
RS65117B1 (sr) 2024-02-29
SI3702351T1 (sl) 2024-03-29
RU2669391C2 (ru) 2018-10-11
HUE065433T2 (hu) 2024-05-28
PT3702351T (pt) 2024-01-17
EP4306171A2 (en) 2024-01-17
CN109336824B (zh) 2022-11-11
JP6737838B2 (ja) 2020-08-12
US10398683B2 (en) 2019-09-03
JP2019194272A (ja) 2019-11-07
FI3702351T3 (fi) 2024-01-24
SMT202400044T1 (it) 2024-03-13
PL2909182T3 (pl) 2020-06-01
JP2018135399A (ja) 2018-08-30
AR099630A1 (es) 2016-08-10
CA2888474A1 (en) 2014-04-24
EP4306171A3 (en) 2024-04-03
HK1214254A1 (en) 2016-07-22
US20200171002A1 (en) 2020-06-04
DK2909182T3 (da) 2020-02-17
US20140128442A1 (en) 2014-05-08
CA3079071C (en) 2022-06-07
US9382212B1 (en) 2016-07-05
CY1122670T1 (el) 2021-03-12
ES2971077T3 (es) 2024-06-03
ES2772498T3 (es) 2020-07-07
BR112015008623A2 (pt) 2017-07-04
US9598376B2 (en) 2017-03-21
RU2015118572A (ru) 2016-12-20
RU2018127873A (ru) 2019-03-14
US20160168104A1 (en) 2016-06-16
CA2888474C (en) 2021-03-02
US10729678B2 (en) 2020-08-04
SI2909182T1 (sl) 2020-03-31
LT3702351T (lt) 2024-01-10
CA3079071A1 (en) 2014-04-24
TW201427956A (zh) 2014-07-16
US20170231963A1 (en) 2017-08-17
WO2014063024A1 (en) 2014-04-24
US9238627B2 (en) 2016-01-19
US9980944B2 (en) 2018-05-29
US20160168102A1 (en) 2016-06-16
EP2909182A1 (en) 2015-08-26
DK3702351T3 (da) 2024-01-29
BR112015008623B1 (pt) 2022-10-25
CN104870427B (zh) 2018-10-23

Similar Documents

Publication Publication Date Title
CN109456272A (zh) Mek抑制剂的制备和包含mek抑制剂的制剂
CN114846006A (zh) 杂环化合物及其制备方法和用途
TWI437988B (zh) 包含N-(5-第三丁基-異噁唑-3-基)-N’-{4-〔7-(2-嗎啉-4-基-乙氧基)咪唑并〔2,1-b〕〔1,3〕苯并噻唑-2-基〕苯基}脲之固體形式物、其組合物及與其有關之用途
TWI732431B (zh) 多形體
WO2016155670A1 (zh) 一种cdk抑制剂和mek抑制剂的共晶及其制备方法
TW202311267A (zh) 咪唑烷酮類化合物的多晶型物、包含其的藥物組合物、其製備方法及其應用
HK40108420A (en) Formulation comprising a mek inhibitor
HK40005916A (en) Preparation of and formulation comprising a mek inhibitor
HK1214254B (en) Preparation of and formulation comprising a mek inhibitor

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
REG Reference to a national code

Ref country code: HK

Ref legal event code: DE

Ref document number: 40005916

Country of ref document: HK