CA2932059C - Crystalline form i of ibrutinib - Google Patents

Crystalline form i of ibrutinib Download PDF

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Publication number
CA2932059C
CA2932059C CA2932059A CA2932059A CA2932059C CA 2932059 C CA2932059 C CA 2932059C CA 2932059 A CA2932059 A CA 2932059A CA 2932059 A CA2932059 A CA 2932059A CA 2932059 C CA2932059 C CA 2932059C
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CA
Canada
Prior art keywords
crystalline form
ibrutinib
ray powder
powder diffraction
diffraction pattern
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.)
Active
Application number
CA2932059A
Other languages
English (en)
French (fr)
Other versions
CA2932059A1 (en
Inventor
Minhua Chen
Yanfeng Zhang
Chaohui YANG
Xiaoyu Zhang
Fei Lu
Heng GE
Peng Wang
Pixu Li
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.)
Crystal Pharmatech Co Ltd
Suzhou Pengxu Pharmatech Co Ltd
Original Assignee
Crystal Pharmatech Co Ltd
Suzhou Pengxu Pharmatech Co Ltd
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Publication date
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Publication of CA2932059A1 publication Critical patent/CA2932059A1/en
Application granted granted Critical
Publication of CA2932059C publication Critical patent/CA2932059C/en
Active legal-status Critical Current
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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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oncology (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA2932059A 2013-11-27 2014-11-26 Crystalline form i of ibrutinib Active CA2932059C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
CN201310616065.4A CN103694241A (zh) 2013-11-27 2013-11-27 Pci-32765的新晶型a及其制备方法
CN201310616065.4 2013-11-27
CN201410542609.1A CN104327085B (zh) 2013-11-27 2014-10-14 Pci-32765的晶型a及其制备方法
CN201410542609.1 2014-10-14
PCT/US2014/067586 WO2015081180A1 (en) 2013-11-27 2014-11-26 Crystalline form i of ibrutinib

Publications (2)

Publication Number Publication Date
CA2932059A1 CA2932059A1 (en) 2015-06-04
CA2932059C true CA2932059C (en) 2019-07-02

Family

ID=50355928

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2932059A Active CA2932059C (en) 2013-11-27 2014-11-26 Crystalline form i of ibrutinib

Country Status (14)

Country Link
US (1) US9751889B2 (enExample)
EP (1) EP3073999B1 (enExample)
JP (1) JP6483126B2 (enExample)
CN (2) CN103694241A (enExample)
AU (1) AU2014354728B2 (enExample)
CA (1) CA2932059C (enExample)
DK (1) DK3073999T3 (enExample)
ES (1) ES2684094T3 (enExample)
HU (1) HUE039718T2 (enExample)
IL (1) IL245865B (enExample)
MX (1) MX363265B (enExample)
PL (1) PL3073999T3 (enExample)
PT (1) PT3073999T (enExample)
WO (1) WO2015081180A1 (enExample)

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WO2013184572A1 (en) 2012-06-04 2013-12-12 Pharmacyclics, Inc. Crystalline forms of a bruton's tyrosine kinase inhibitor
US9884869B2 (en) 2014-03-27 2018-02-06 Perrigo Api Ltd. Ibrutinib solid forms and production process therefor
CN105085529A (zh) * 2014-05-15 2015-11-25 广东东阳光药业有限公司 依鲁替尼新晶型及其制备方法
US9545407B2 (en) 2014-08-07 2017-01-17 Pharmacyclics Llc Formulations of a bruton's tyrosine kinase inhibitor
EP3180343A1 (en) * 2014-08-14 2017-06-21 Assia Chemical Industries Ltd. Solid state forms of ibrutinib
CZ201584A3 (cs) 2015-02-09 2016-08-17 Zentiva, K.S. Sůl Ibrutinib sulfátu
US10477780B2 (en) * 2015-02-13 2019-11-19 Hgci, Inc. Multiple cell tray with media plugs
IL315294A (en) 2015-03-03 2024-10-01 Pharmacyclics Llc Pharmaceutical formulations of bruton's tyrosine kinase inhibitor
AU2016236578B2 (en) * 2015-03-20 2019-04-04 Crystal Pharmatech Co., Ltd. Preparation method of crystalline form a of pci-32765
CN106153797B (zh) * 2015-04-20 2017-08-29 北京睿创康泰医药研究院有限公司 一种依鲁替尼及依鲁替尼制剂有关物质分析方法
CN106153798B (zh) * 2015-04-22 2017-08-29 北京睿创康泰医药研究院有限公司 一种用于分析依鲁替尼及依鲁替尼制剂有关物质的hplc方法以及这些杂质做参比标准的用途
EP3337485B1 (en) 2015-08-19 2021-03-17 Sun Pharmaceutical Industries Ltd Crystalline forms of ibrutinib
ITUB20155616A1 (it) * 2015-11-16 2017-05-16 Laboratorio Chimico Int S P A Procedimento per la preparazione della forma amorfa dell?ibrutinib e nuova forma cristallina.
CN105294696A (zh) * 2015-11-19 2016-02-03 上海创诺医药集团有限公司 依鲁替尼新晶型及其制备方法
CN106905320A (zh) * 2015-12-23 2017-06-30 杭州容立医药科技有限公司 一种适合药用的依鲁替尼及其制剂
CN106995445B (zh) * 2016-01-22 2021-08-03 山东新时代药业有限公司 一种布鲁顿酪氨酸激酶抑制剂晶型及其制备方法
CN107286163A (zh) * 2016-03-30 2017-10-24 上海星泰医药科技有限公司 一种依鲁替尼的新晶型及其制备方法
CZ2016196A3 (cs) 2016-04-06 2017-10-18 Zentiva, K.S. Pevné formy Ibrutinibu
CZ2016276A3 (cs) 2016-05-11 2017-11-22 Zentiva, K.S. Pevné formy volné báze ibrutinibu
CN106117214A (zh) * 2016-06-29 2016-11-16 上海创诺医药集团有限公司 依鲁替尼新晶型及其制备方法
CN106008529A (zh) * 2016-08-08 2016-10-12 上海工程技术大学 一种依鲁替尼溶剂化物及其制备方法
US10183024B2 (en) 2016-12-02 2019-01-22 Apotex Inc. Crystalline forms of ibrutinib
WO2019070698A1 (en) 2017-10-02 2019-04-11 Johnson Matthey Public Limited Company Novel forms of ibrutinib
CZ2017787A3 (cs) 2017-12-08 2019-06-19 Zentiva, K.S. Farmaceutické kompozice obsahující ibrutinib
WO2019195827A1 (en) 2018-04-06 2019-10-10 Johnson Matthey Public Limited Company Novel form of ibrutinib
US20220009929A1 (en) 2018-05-02 2022-01-13 Cipla Limited Polymorphic forms of ibrutinib
JP7410877B2 (ja) 2018-05-03 2024-01-10 ジュノー セラピューティクス インコーポレイテッド キメラ抗原受容体（ｃａｒ）ｔ細胞療法とキナーゼ阻害剤の併用療法
EP3575300A1 (en) 2018-05-31 2019-12-04 Apotex Inc. Novel crystalline forms of ibrutinib
EP3810590A1 (en) * 2018-06-19 2021-04-28 Merck Patent GmbH Novel crystalline forms of 1-(4-{[6-amino-5-(4-phenoxy-phenyl)-pyrimidin-4-ylamino]-methyl}-4-fluoro-piperidin-1-yl)-propenone, salt forms thereof, and processes to obtain
CN111138436A (zh) * 2018-11-04 2020-05-12 鲁南制药集团股份有限公司 伊布替尼晶型a单晶及其制备方法
US10688050B1 (en) 2018-12-21 2020-06-23 Synthon B.V. Pharmaceutical composition comprising ibrutinib
EP3669867A1 (en) 2018-12-21 2020-06-24 Synthon B.V. Pharmaceutical composition comprising ibrutinib
CN113214261A (zh) * 2020-01-21 2021-08-06 尚科生物医药（上海）有限公司 一种依鲁替尼晶型a的纯化方法
WO2022260667A1 (en) 2021-06-10 2022-12-15 Hikma Pharmaceuticals Usa Inc. Oral dosage forms of ibrutinib
US11433072B1 (en) * 2021-06-10 2022-09-06 Hikma Pharmaceuticals USA, Inc. Oral dosage forms of ibrutinib
US20250302954A1 (en) 2022-05-11 2025-10-02 Celgene Corporation Methods to overcome drug resistance by re-sensitizing cancer cells to treatment with a prior therapy via treatment with a t cell therapy
WO2023242384A1 (en) 2022-06-17 2023-12-21 Krka, D.D., Novo Mesto Crystalline form of ibrutinib

Family Cites Families (8)

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CA2645583A1 (en) 2006-03-20 2007-09-27 F. Hoffman-La Roche Ag Methods of inhibiting btk and syk protein kinases
PL2526933T3 (pl) * 2006-09-22 2015-08-31 Pharmacyclics Llc Inhibitory kinazy tyrozynowej Brutona
CN105566229A (zh) 2010-08-10 2016-05-11 西建阿维拉米斯研究公司 Btk抑制剂的苯磺酸盐及其用途和制备方法
ES2681050T3 (es) * 2012-04-11 2018-09-11 Acerta Pharma B.V. Inhibidores de la tirosina quinasa de Bruton para la movilización hematopoyética
WO2013157021A1 (en) 2012-04-20 2013-10-24 Advinus Therapeutics Limited Bicyclic compounds, compositions and medicinal applications thereof
WO2013184572A1 (en) * 2012-06-04 2013-12-12 Pharmacyclics, Inc. Crystalline forms of a bruton's tyrosine kinase inhibitor
CN103121999A (zh) * 2012-08-29 2013-05-29 苏州迪飞医药科技有限公司 一种酪氨酸激酶抑制剂pci-32765的合成方法
CN103142601A (zh) * 2013-03-13 2013-06-12 杭州雷索药业有限公司 Pci-32765在制备抗血管生成类药物中的应用

Also Published As

Publication number Publication date
EP3073999A1 (en) 2016-10-05
ES2684094T3 (es) 2018-10-01
AU2014354728A1 (en) 2016-06-16
CN104327085A (zh) 2015-02-04
JP2016538314A (ja) 2016-12-08
DK3073999T3 (en) 2018-09-03
CN103694241A (zh) 2014-04-02
CA2932059A1 (en) 2015-06-04
EP3073999B1 (en) 2018-05-30
EP3073999A4 (en) 2017-03-22
AU2014354728B2 (en) 2019-02-28
MX363265B (es) 2019-03-19
US20170002009A1 (en) 2017-01-05
HUE039718T2 (hu) 2019-02-28
PL3073999T3 (pl) 2018-10-31
IL245865B (en) 2019-05-30
PT3073999T (pt) 2018-10-16
WO2015081180A1 (en) 2015-06-04
CN104327085B (zh) 2016-08-24
JP6483126B2 (ja) 2019-03-13
US9751889B2 (en) 2017-09-05
IL245865A0 (en) 2016-07-31
MX2016006901A (es) 2016-10-28

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