GB2556535A - A method for preparation of ibrutinib precursor - Google Patents

A method for preparation of ibrutinib precursor Download PDF

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Publication number
GB2556535A
GB2556535A GB1800657.7A GB201800657A GB2556535A GB 2556535 A GB2556535 A GB 2556535A GB 201800657 A GB201800657 A GB 201800657A GB 2556535 A GB2556535 A GB 2556535A
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GB
United Kingdom
Prior art keywords
ibrutinib
precursor
preparation
pyrimidin
piperidin
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
GB1800657.7A
Other versions
GB201800657D0 (en
GB2556535B (en
Inventor
Lebedevs Antons
Ponomarjovs Jurijs
Varaceva Larisa
Cernaks Dmitrijs
Cernobrovijs Aleksandrs
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 GB201800657D0 publication Critical patent/GB201800657D0/en
Publication of GB2556535A publication Critical patent/GB2556535A/en
Application granted granted Critical
Publication of GB2556535B publication Critical patent/GB2556535B/en
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

Abstract

A method for the preparation of ibrutinib's precursor, 3-(4-phenoxyphenyl)-1-((3R)-piperidin-3-il)-1H-pyrazolof [3,4-d]|pyrimidin-4-amine, involving arylation of N-protected 1-(piperidin-3-yl)pyrazolo[3,4-d]pyrimidin-4-amine in the presence of palladium catalyst, nitrogen-containing ligand, and base, with subsequent removal of the protecting groups by known methods, is reported. (Formula (II))
GB1800657.7A 2015-08-31 2015-11-13 A method for preparation of ibrutinib precursor Active GB2556535B (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
LVP-15-98A LV15201B (en) 2015-08-31 2015-08-31 The method for the preparation of ibrutinib intermediate
PCT/LV2015/000009 WO2017039425A1 (en) 2015-08-31 2015-11-13 A method for preparation of ibrutinib precursor

Publications (3)

Publication Number Publication Date
GB201800657D0 GB201800657D0 (en) 2018-02-28
GB2556535A true GB2556535A (en) 2018-05-30
GB2556535B GB2556535B (en) 2020-10-14

Family

ID=54754721

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1800657.7A Active GB2556535B (en) 2015-08-31 2015-11-13 A method for preparation of ibrutinib precursor

Country Status (4)

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

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107674079B (en) * 2017-09-27 2019-12-13 黑龙江珍宝岛药业股份有限公司 Synthesis method of ibrutinib
CN113200986A (en) * 2021-04-29 2021-08-03 湖南华腾制药有限公司 Preparation method of ibrutinib intermediate
CN114940678B (en) * 2021-09-26 2023-02-07 上海贵之言医药科技有限公司 Pyrazolopyrimidine ester compound

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012158795A1 (en) * 2011-05-17 2012-11-22 Principia Biopharma Inc. Pyrazolopyrimidine derivatives as tyrosine kinase inhibitors
WO2014139970A1 (en) * 2013-03-15 2014-09-18 Janssen Pharmaceutica Nv Processes and intermediates for preparing a medicament

Family Cites Families (4)

* 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
EP2560007A1 (en) 2007-03-28 2013-02-20 Pharmacyclics, Inc. Identification of bruton's tyrosine kinase inhibitors
JP2011503103A (en) 2007-11-07 2011-01-27 フォールドアールエックス ファーマシューティカルズ インコーポレーティッド Methods for regulating protein transport
WO2012058645A1 (en) 2010-10-29 2012-05-03 Biogen Idec Ma Inc. Heterocyclic tyrosine kinase inhibitors

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012158795A1 (en) * 2011-05-17 2012-11-22 Principia Biopharma Inc. Pyrazolopyrimidine derivatives as tyrosine kinase inhibitors
WO2014139970A1 (en) * 2013-03-15 2014-09-18 Janssen Pharmaceutica Nv Processes and intermediates for preparing a medicament

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
European Journal of Organic Chemistry, vol. 2012, no. 36, 2012, A. Ben-Yahia et al., "Direct C-3 arylation sof 1H-indazoles", pp. 7075-7081. *

Also Published As

Publication number Publication date
LV15201A (en) 2017-03-20
CA2987708C (en) 2022-08-02
WO2017039425A1 (en) 2017-03-09
LV15201B (en) 2017-07-20
CA2987708A1 (en) 2017-03-09
GB201800657D0 (en) 2018-02-28
GB2556535B (en) 2020-10-14

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