WO2018121228A1 - Composé ayant une activité inhibitrice d'axl, sa méthode de préparation et son utilisation - Google Patents

Composé ayant une activité inhibitrice d'axl, sa méthode de préparation et son utilisation Download PDF

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Publication number
WO2018121228A1
WO2018121228A1 PCT/CN2017/115380 CN2017115380W WO2018121228A1 WO 2018121228 A1 WO2018121228 A1 WO 2018121228A1 CN 2017115380 W CN2017115380 W CN 2017115380W WO 2018121228 A1 WO2018121228 A1 WO 2018121228A1
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methyl
substituted
unsubstituted
pyrrolo
group
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PCT/CN2017/115380
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English (en)
Chinese (zh)
Inventor
段文虎
耿美玉
王蔚
丁健
艾菁
许丹丹
彭霞
曹素芬
季寅淳
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中国科学院上海药物研究所
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Priority to CN201780074009.9A priority Critical patent/CN110036014B/zh
Publication of WO2018121228A1 publication Critical patent/WO2018121228A1/fr

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    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • 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
    • A61K31/695—Silicon compounds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage

Definitions

  • R 5 is selected from H, substituted or unsubstituted C1-C4 alkyl, halogen, substituted or unsubstituted C1-C4 alkoxy.
  • R 5 is selected from the group consisting of H, methyl, F, Cl, and methoxy.
  • R 6 is H.
  • R 1 is selected from substituted or unsubstituted 6-10 membered aryl, substituted or unsubstituted 5-10 membered heteroaryl containing 1-3 selected from N, O and S heteroatoms.
  • substituted means that one or more hydrogen atoms on the group are substituted with a substituent selected from the group consisting of a further substituted or unsubstituted C1-C4 alkyl group, a halogen, a cyano group, an amino group, a further substitution or Unsubstituted C1-C4 alkoxy group and further substituted or unsubstituted C1-C4 alkylthio group.
  • R 2 is selected from H, substituted or unsubstituted C1-C4 alkyl, substituted or unsubstituted C3-C6 cycloalkyl, substituted or unsubstituted, and 1-3 are selected from N, a 3-8 membered heterocycloalkyl group of O and S heteroatoms; said "substituted” means that one or more hydrogen atoms on the group are substituted with a substituent selected from the group consisting of a further substituted or unsubstituted C1- a C4 alkyl group, a further substituted or unsubstituted C1-C4 alkoxy group, a substituted or unsubstituted C1-C4 alkylamino group, a substituted or unsubstituted C1-C4 alkylthio group, containing 1-3 selected from N, a 3-8 membered heterocycloalkyl group of O and S heteroatoms and -CONR 10 R 11
  • the GAS6/AXL signaling pathway abnormal expression related diseases are colon cancer, rectal cancer, skin cancer, gastric cancer, lung cancer, endometrial cancer, malignant melanoma, thyroid cancer, glioma, esophagus Tumors associated with poor prognosis such as cancer, prostate cancer, ovarian cancer, and breast cancer, and their high expression may mediate acquired resistance to EGFR.
  • the compound of the present invention is as shown in the general formula (I):
  • amine salt and other pharmaceutically acceptable amine salts (such as methylamine salt, ethylamine salt, propylamine salt, dimethylamine salt, trimethylamine salt, diethylamine salt, triethylamine salt, tert-butyl) a base amine salt, an ethylenediamine salt, a glycolic acid amine salt, a dihydroxyethylamine salt, a trishydroxyethylamine salt, and an amine salt formed from morpholine, piperazine, and lysine, respectively.
  • amine salt such as methylamine salt, ethylamine salt, propylamine salt, dimethylamine salt, trimethylamine salt, diethylamine salt, triethylamine salt, tert-butyl
  • base amine salt such as methylamine salt, ethylamine salt, propylamine salt, dimethylamine salt, trimethylamine salt, diethylamine salt, triethylamine salt, tert-buty
  • Dosage forms for the compounds of the invention for topical administration include ointments, powders, patches, propellants and inhalants.
  • the active ingredient is admixed under sterile conditions with a physiologically acceptable carrier and any preservatives, buffers, or, if necessary, propellants.
  • Step 1 Preparation of ethyl 3-oxo-4-phenylbutanoate
  • Step 5 Preparation of N-(5-(4-amino-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)pyridin-2-yl)-5-(4-fluorobenzene 4-oxo-1-((tetrahydro-2H-pyran-4-yl)methyl)-1,4-dihydropyridine-3-carboxamide
  • Step 1 Preparation of 4-chloro-5-iodo-7-((1-methylpiperidin-4-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidine
  • Step 4 Preparation of N-(4-(4-amino-7-((tetrahydro-2H-pyran-4-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl Phenyl)-5-(4-fluorophenyl)-4-oxo-1-((tetrahydro-2H-pyran-4-yl)methyl)-1,4-dihydropyridine-3- Formamide
  • Example 38 N-(4-(4-Amino-7-(tetrahydro-2H-pyran-4-yl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenyl) -5-(4-fluorophenyl)-4-oxo-1-((tetrahydro-2H-pyran-4-yl)methyl)-1,4-dihydropyridine-3-carboxamide (NO .38)
  • Step 3 Preparation of 5-(3,5-difluorophenyl)-4-oxo-1-((tetrahydro-2H-pyran-4-yl)methyl)-1,4-dihydropyridine- Ethyl 3-carboxylate
  • Step 2 Preparation of ethyl 4-(3-fluorophenyl)-3-oxobutanoate
  • Step 2 Preparation of ethyl 4-(4-(methylthio)phenyl)-3-oxobutanoate

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne un composé ayant des activités inhibitrices d'AXL, sa méthode de préparation et son utilisation. En particulier, l'invention concerne un composé de structure telle que représentée par la formule (I), chaque groupe et son substituant étant tels que définis dans la description. L'invention concerne en outre une méthode de préparation du composé décrit et son utilisation en tant qu'inhibiteur d'une protéine tyrosine kinase, en particulier en tant qu'inhibiteur d'AXL, dans des médicaments pour le traitement de maladies associées au cancer.
PCT/CN2017/115380 2016-12-28 2017-12-11 Composé ayant une activité inhibitrice d'axl, sa méthode de préparation et son utilisation WO2018121228A1 (fr)

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CN201780074009.9A CN110036014B (zh) 2016-12-28 2017-12-11 一种具有axl抑制活性的化合物及其制备和应用

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CN201611237355.8 2016-12-28
CN201611237355.8A CN108250200A (zh) 2016-12-28 2016-12-28 一种具有Axl抑制活性的化合物及其制备和应用

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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2020188015A1 (fr) 2019-03-21 2020-09-24 Onxeo Molécule dbait associée à un inhibiteur de kinase pour le traitement du cancer
WO2021089791A1 (fr) 2019-11-08 2021-05-14 INSERM (Institut National de la Santé et de la Recherche Médicale) Méthodes pour le traitement de cancers qui ont acquis une résistance aux inhibiteurs de kinase
WO2021148581A1 (fr) 2020-01-22 2021-07-29 Onxeo Nouvelle molécule dbait et son utilisation
WO2021155004A1 (fr) * 2020-01-30 2021-08-05 The Regents Of The University Of California Agents de liaison à strad et leurs utilisations
US11104676B2 (en) 2018-08-30 2021-08-31 Array Biopharma Inc. Pyrazolo[3,4-b]pyridine compounds as inhibitors of TAM and MET kinases
CN113683629A (zh) * 2020-05-18 2021-11-23 北京范恩柯尔生物科技有限公司 取代的杂芳基化合物及其组合物和用途
WO2021252488A1 (fr) 2020-06-08 2021-12-16 Halia Therapeutics, Inc. Inhibiteurs de la kinase nek7
WO2022007921A1 (fr) * 2020-07-10 2022-01-13 北京范恩柯尔生物科技有限公司 Composé triazine, composition et utilisation associées
WO2022242752A1 (fr) * 2021-05-21 2022-11-24 江苏恒瑞医药股份有限公司 Procédé de préparation d'un intermédiaire d'inhibiteur de btk
US11945785B2 (en) 2021-12-30 2024-04-02 Biomea Fusion, Inc. Pyrazine compounds as inhibitors of FLT3

Families Citing this family (10)

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CN110041316B (zh) * 2018-01-17 2022-04-19 药捷安康(南京)科技股份有限公司 Tam家族激酶/和csf1r激酶抑制剂及其用途
CN110627796B (zh) * 2018-06-21 2022-07-12 北京越之康泰生物医药科技有限公司 含氮杂环类衍生物及其在医药上的应用
CN111689991B (zh) * 2019-03-13 2023-06-09 习峰 取代的杂芳基化合物及其组合物和用途
WO2020182188A1 (fr) * 2019-03-13 2020-09-17 习峰 Composé hétéroaryle substitué, composition correspondante et utilisations associées
CN114555588B (zh) * 2019-11-07 2024-08-06 南京正大天晴制药有限公司 作为axl抑制剂的喹唑啉类化合物
CN116583287A (zh) * 2021-02-05 2023-08-11 四川科伦博泰生物医药股份有限公司 一类哒嗪酮杂环化合物及其制备方法和用途
WO2023016296A1 (fr) * 2021-08-12 2023-02-16 四川科伦博泰生物医药股份有限公司 Composé hétérocyclique, son procédé de préparation et son utilisation
WO2023155886A1 (fr) * 2022-02-17 2023-08-24 Shanghai Antengene Corporation Limited Composés de pyrazolopyridine utiles en tant qu'inhibiteurs de tam
CN115340557A (zh) * 2022-09-19 2022-11-15 安徽大学 一种4-氯-5-碘-7-甲基-7H-吡咯并[2,3-d]嘧啶的合成方法
CN115745993B (zh) * 2022-11-08 2024-03-12 上海皓元生物医药科技有限公司 一种mpo抑制剂的制备方法

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WO2016006706A1 (fr) * 2014-07-07 2016-01-14 第一三共株式会社 Dérivé de pyridone ayant un groupe tétrahydropyranyl méthyle
CN105408312A (zh) * 2013-07-24 2016-03-16 小野药品工业株式会社 喹啉衍生物
EP3067356A1 (fr) * 2013-11-08 2016-09-14 ONO Pharmaceutical Co., Ltd. Dérivé de pyrrolopyrimidine

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101296928A (zh) * 2005-10-28 2008-10-29 Irm责任有限公司 作为蛋白激酶抑制剂的化合物和组合物
CN102131783A (zh) * 2008-04-16 2011-07-20 马克斯普朗克科学发展组织 作为axl激酶抑制剂的喹啉衍生物
CN102216300A (zh) * 2009-09-30 2011-10-12 浙江贝达药业有限公司 作为蛋白激酶抑制剂的化合物和组合物
CN103958497A (zh) * 2011-11-14 2014-07-30 赛福伦公司 作为AXL和c-MET激酶抑制剂的尿嘧啶衍生物
CN104185627A (zh) * 2012-01-31 2014-12-03 第一三共株式会社 吡啶酮衍生物
CN105408312A (zh) * 2013-07-24 2016-03-16 小野药品工业株式会社 喹啉衍生物
EP3067356A1 (fr) * 2013-11-08 2016-09-14 ONO Pharmaceutical Co., Ltd. Dérivé de pyrrolopyrimidine
WO2016006706A1 (fr) * 2014-07-07 2016-01-14 第一三共株式会社 Dérivé de pyridone ayant un groupe tétrahydropyranyl méthyle

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11104676B2 (en) 2018-08-30 2021-08-31 Array Biopharma Inc. Pyrazolo[3,4-b]pyridine compounds as inhibitors of TAM and MET kinases
US11780835B2 (en) 2018-08-30 2023-10-10 Array Biopharma Inc. Pyrazolo[3,4-b]pyridine compounds as inhibitors of TAM and MET kinases
WO2020188015A1 (fr) 2019-03-21 2020-09-24 Onxeo Molécule dbait associée à un inhibiteur de kinase pour le traitement du cancer
WO2021089791A1 (fr) 2019-11-08 2021-05-14 INSERM (Institut National de la Santé et de la Recherche Médicale) Méthodes pour le traitement de cancers qui ont acquis une résistance aux inhibiteurs de kinase
WO2021148581A1 (fr) 2020-01-22 2021-07-29 Onxeo Nouvelle molécule dbait et son utilisation
WO2021155004A1 (fr) * 2020-01-30 2021-08-05 The Regents Of The University Of California Agents de liaison à strad et leurs utilisations
WO2021233236A1 (fr) * 2020-05-18 2021-11-25 北京范恩柯尔生物科技有限公司 Composé hétéroaryle substitué, composition et utilisation associées
CN113683629A (zh) * 2020-05-18 2021-11-23 北京范恩柯尔生物科技有限公司 取代的杂芳基化合物及其组合物和用途
WO2021252488A1 (fr) 2020-06-08 2021-12-16 Halia Therapeutics, Inc. Inhibiteurs de la kinase nek7
WO2022007921A1 (fr) * 2020-07-10 2022-01-13 北京范恩柯尔生物科技有限公司 Composé triazine, composition et utilisation associées
JP7556604B2 (ja) 2020-07-10 2024-09-26 範恩柯爾生物科技（中山）有限公司 トリアジン系化合物およびその組成物と用途
WO2022242752A1 (fr) * 2021-05-21 2022-11-24 江苏恒瑞医药股份有限公司 Procédé de préparation d'un intermédiaire d'inhibiteur de btk
US11945785B2 (en) 2021-12-30 2024-04-02 Biomea Fusion, Inc. Pyrazine compounds as inhibitors of FLT3

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CN110036014A (zh) 2019-07-19
CN110036014B (zh) 2021-09-07

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