CA2987708A1 - Procede de preparation de precurseur d'ibrutinib - Google Patents

Procede de preparation de precurseur d'ibrutinib Download PDF

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Publication number
CA2987708A1
CA2987708A1 CA2987708A CA2987708A CA2987708A1 CA 2987708 A1 CA2987708 A1 CA 2987708A1 CA 2987708 A CA2987708 A CA 2987708A CA 2987708 A CA2987708 A CA 2987708A CA 2987708 A1 CA2987708 A1 CA 2987708A1
Authority
CA
Canada
Prior art keywords
compound
boc
cbz
ibrutinib
arylation
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.)
Granted
Application number
CA2987708A
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English (en)
Other versions
CA2987708C (fr
Inventor
Antons Lebedevs
Jurijs PONOMARJOVS
Larisa VARACEVA
Dmitrijs CERNAKS
Aleksandrs Cernobrovijs
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.)
Latvian Institute of Organic Synthesis
Original Assignee
Latvian Institute of Organic Synthesis
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 Latvian Institute of Organic Synthesis filed Critical Latvian Institute of Organic Synthesis
Publication of CA2987708A1 publication Critical patent/CA2987708A1/fr
Application granted granted Critical
Publication of CA2987708C publication Critical patent/CA2987708C/fr
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • 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
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Epidemiology (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

L'invention concerne un procédé de préparation de précurseur d'ibrutinib, 3-(4-phénoxyphényl)-1-((3R)-pipéridin-3-yl)-1H-pyrazolo[3,4-d]-pyrimidin-4-amine, impliquant l'arylation de 1-(pipéridin-3-yl)pyrazolo[3,4-d]pyrimidin-4-amine N-protégée en présence d'un catalyseur au palladium, d'un ligand contenant de l'azote et d'une base, avec le retrait consécutif des groupes protecteurs par des procédés connus. (Formule (II))
CA2987708A 2015-08-31 2015-11-13 Procede de preparation de precurseur d'ibrutinib Active CA2987708C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
LVP-15-98A LV15201B (lv) 2015-08-31 2015-08-31 Ibrutiniba izejvielas iegūšanas paņēmiens
LVP-15-98 2015-08-31
PCT/LV2015/000009 WO2017039425A1 (fr) 2015-08-31 2015-11-13 Procédé de préparation de précurseur d'ibrutinib

Publications (2)

Publication Number Publication Date
CA2987708A1 true CA2987708A1 (fr) 2017-03-09
CA2987708C CA2987708C (fr) 2022-08-02

Family

ID=54754721

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2987708A Active CA2987708C (fr) 2015-08-31 2015-11-13 Procede de preparation de precurseur d'ibrutinib

Country Status (4)

Country Link
CA (1) CA2987708C (fr)
GB (1) GB2556535B (fr)
LV (1) LV15201B (fr)
WO (1) WO2017039425A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107674079B (zh) * 2017-09-27 2019-12-13 黑龙江珍宝岛药业股份有限公司 一种伊布替尼的合成方法
CN113200986A (zh) * 2021-04-29 2021-08-03 湖南华腾制药有限公司 一种伊布替尼中间体的制备方法
CN114940678B (zh) * 2021-09-26 2023-02-07 上海贵之言医药科技有限公司 一种吡唑并嘧啶酯类化合物

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20080007621A1 (en) 2006-07-06 2008-01-10 Sbc Knowledge Ventures, Lp System and method of controlling access to an entrance
SG10202107066WA (en) 2007-03-28 2021-07-29 Pharmacyclics Llc Inhibitors of bruton's tyrosine kinase
CA2705303A1 (fr) 2007-11-07 2009-05-14 Foldrx Pharmaceuticals, Inc. Regulation du trafic de proteines
WO2012058645A1 (fr) 2010-10-29 2012-05-03 Biogen Idec Ma Inc. Inhibiteurs de tyrosine kinase hétérocycliques
WO2012158795A1 (fr) 2011-05-17 2012-11-22 Principia Biopharma Inc. Dérivés de pyrazolopyrimidine utilisés comme inhibiteurs de tyrosine kinase
CA2901510C (fr) * 2013-03-15 2022-11-29 Janssen Pharmaceutica Nv Procedes pour preparer les derives d'ibrutinib et leurs intermediaires

Also Published As

Publication number Publication date
GB2556535B (en) 2020-10-14
GB2556535A (en) 2018-05-30
GB201800657D0 (en) 2018-02-28
WO2017039425A1 (fr) 2017-03-09
CA2987708C (fr) 2022-08-02
LV15201B (lv) 2017-07-20
LV15201A (lv) 2017-03-20

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Effective date: 20200715