CA2932059C - Crystalline form i of ibrutinib - Google Patents
Crystalline form i of ibrutinib Download PDFInfo
- 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
- Authority
- 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.)
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Links
- XYFPWWZEPKGCCK-GOSISDBHSA-N ibrutinib Chemical compound C1=2C(N)=NC=NC=2N([C@H]2CN(CCC2)C(=O)C=C)N=C1C(C=C1)=CC=C1OC1=CC=CC=C1 XYFPWWZEPKGCCK-GOSISDBHSA-N 0.000 title claims abstract description 43
- 239000002177 L01XE27 - Ibrutinib Substances 0.000 title claims abstract description 34
- 229960001507 ibrutinib Drugs 0.000 title claims abstract description 34
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 30
- 238000000034 method Methods 0.000 claims abstract description 18
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 11
- 102000001714 Agammaglobulinaemia Tyrosine Kinase Human genes 0.000 claims abstract description 10
- 108010029445 Agammaglobulinaemia Tyrosine Kinase Proteins 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 10
- 201000010099 disease Diseases 0.000 claims abstract description 7
- 208000035475 disorder Diseases 0.000 claims abstract description 7
- 230000000694 effects Effects 0.000 claims abstract description 6
- 238000000113 differential scanning calorimetry Methods 0.000 claims abstract description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 12
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 12
- 230000005855 radiation Effects 0.000 claims description 10
- 208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 9
- 150000002576 ketones Chemical class 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 208000025205 Mantle-Cell Lymphoma Diseases 0.000 claims description 8
- 238000002411 thermogravimetry Methods 0.000 claims description 8
- 206010028980 Neoplasm Diseases 0.000 claims description 7
- 210000003719 b-lymphocyte Anatomy 0.000 claims description 7
- 201000011510 cancer Diseases 0.000 claims description 7
- 238000001757 thermogravimetry curve Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims description 6
- 208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 6
- 206010012818 diffuse large B-cell lymphoma Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 229910016523 CuKa Inorganic materials 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 230000036210 malignancy Effects 0.000 claims description 4
- 208000034578 Multiple myelomas Diseases 0.000 claims description 3
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims 1
- 230000008018 melting Effects 0.000 claims 1
- 102000004169 proteins and genes Human genes 0.000 abstract 1
- 108090000623 proteins and genes Proteins 0.000 abstract 1
- 239000007909 solid dosage form Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 5
- 239000012453 solvate Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000001179 sorption measurement Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 108091008875 B cell receptors Proteins 0.000 description 2
- -1 but not limited to Substances 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000006186 oral dosage form Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- 230000011664 signaling Effects 0.000 description 2
- 238000013097 stability assessment Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
- 229940124291 BTK inhibitor Drugs 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 241001397173 Kali <angiosperm> Species 0.000 description 1
- 229910013470 LiC1 Inorganic materials 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 210000001744 T-lymphocyte Anatomy 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000013481 data capture Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000011067 equilibration Methods 0.000 description 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 210000003958 hematopoietic stem cell Anatomy 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Inorganic materials [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 210000000822 natural killer cell Anatomy 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 239000011863 silicon-based powder Substances 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000004441 surface measurement Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310616065.4 | 2013-11-27 | ||
| CN201310616065.4A CN103694241A (zh) | 2013-11-27 | 2013-11-27 | Pci-32765的新晶型a及其制备方法 |
| CN201410542609.1 | 2014-10-14 | ||
| CN201410542609.1A CN104327085B (zh) | 2013-11-27 | 2014-10-14 | Pci-32765的晶型a及其制备方法 |
| 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) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20250151610A (ko) | 2012-06-04 | 2025-10-21 | 파마싸이클릭스 엘엘씨 | 브루톤 타이로신 키나아제 저해제의 결정 형태 |
| EP3122753A4 (en) | 2014-03-27 | 2017-11-29 | 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 |
| CA2955747A1 (en) | 2014-08-07 | 2016-02-11 | Pharmacyclics Llc | Novel formulations of a bruton's tyrosine kinase inhibitor |
| US10035802B2 (en) | 2014-08-14 | 2018-07-31 | Teva Pharmaceuticals Usa, Inc. | 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 |
| CN105669679A (zh) * | 2015-03-20 | 2016-06-15 | 苏州晶云药物科技有限公司 | 一种pci-32765晶型a的制备方法 |
| 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 |
| EP3787751A1 (en) | 2018-05-03 | 2021-03-10 | Juno Therapeutics, Inc. | Combination therapy of a chimeric antigen receptor (car) t cell therapy and a kinase inhibitor |
| EP3575300A1 (en) | 2018-05-31 | 2019-12-04 | Apotex Inc. | Novel crystalline forms of ibrutinib |
| KR20210022674A (ko) * | 2018-06-19 | 2021-03-03 | 메르크 파텐트 게엠베하 | 1-(4-｛[6-아미노-5-(4-페녹시-페닐)-피리미딘-4-일아미노]-메틸｝-4-플루오로-피페리딘-1-일)-프로펜온의 신규한 결정 형태, 이의 염 형태, 및 이를 수득하는 방법 |
| 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 |
| EP3669867A1 (en) | 2018-12-21 | 2020-06-24 | Synthon B.V. | Pharmaceutical composition comprising ibrutinib |
| US10688050B1 (en) | 2018-12-21 | 2020-06-23 | 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 |
| TN2023000295A1 (en) | 2021-06-10 | 2025-07-02 | 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)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007107469A1 (en) | 2006-03-20 | 2007-09-27 | F. Hoffmann-La Roche Ag | Methods of inhibiting btk and syk protein kinases |
| DK2529622T3 (en) * | 2006-09-22 | 2018-05-07 | Pharmacyclics Llc | INHIBITORS OF BRUTON-TYROSINKINASE |
| ES2617763T3 (es) * | 2010-08-10 | 2017-06-19 | Celgene Avilomics Research, Inc. | Sal de besilato de un inhibidor de BTK |
| US9522917B2 (en) | 2012-04-11 | 2016-12-20 | Acerta Pharma B.V. | Bruton's tyrosine kinase inhibitors for hematopoietic mobilization |
| WO2013157021A1 (en) * | 2012-04-20 | 2013-10-24 | Advinus Therapeutics Limited | Bicyclic compounds, compositions and medicinal applications thereof |
| KR20250151610A (ko) * | 2012-06-04 | 2025-10-21 | 파마싸이클릭스 엘엘씨 | 브루톤 타이로신 키나아제 저해제의 결정 형태 |
| 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 |
-
2013
- 2013-11-27 CN CN201310616065.4A patent/CN103694241A/zh active Pending
-
2014
- 2014-10-14 CN CN201410542609.1A patent/CN104327085B/zh active Active
- 2014-11-26 AU AU2014354728A patent/AU2014354728B2/en active Active
- 2014-11-26 ES ES14866302.4T patent/ES2684094T3/es active Active
- 2014-11-26 CA CA2932059A patent/CA2932059C/en active Active
- 2014-11-26 DK DK14866302.4T patent/DK3073999T3/en active
- 2014-11-26 PT PT14866302T patent/PT3073999T/pt unknown
- 2014-11-26 PL PL14866302T patent/PL3073999T3/pl unknown
- 2014-11-26 US US15/100,247 patent/US9751889B2/en active Active
- 2014-11-26 EP EP14866302.4A patent/EP3073999B1/en active Active
- 2014-11-26 HU HUE14866302A patent/HUE039718T2/hu unknown
- 2014-11-26 WO PCT/US2014/067586 patent/WO2015081180A1/en not_active Ceased
- 2014-11-26 JP JP2016535162A patent/JP6483126B2/ja active Active
- 2014-11-26 MX MX2016006901A patent/MX363265B/es unknown
-
2016
- 2016-05-26 IL IL245865A patent/IL245865B/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| MX2016006901A (es) | 2016-10-28 |
| CN104327085A (zh) | 2015-02-04 |
| IL245865B (en) | 2019-05-30 |
| ES2684094T3 (es) | 2018-10-01 |
| CN104327085B (zh) | 2016-08-24 |
| HUE039718T2 (hu) | 2019-02-28 |
| EP3073999A4 (en) | 2017-03-22 |
| JP2016538314A (ja) | 2016-12-08 |
| PT3073999T (pt) | 2018-10-16 |
| WO2015081180A1 (en) | 2015-06-04 |
| MX363265B (es) | 2019-03-19 |
| PL3073999T3 (pl) | 2018-10-31 |
| CN103694241A (zh) | 2014-04-02 |
| US20170002009A1 (en) | 2017-01-05 |
| AU2014354728B2 (en) | 2019-02-28 |
| DK3073999T3 (en) | 2018-09-03 |
| EP3073999A1 (en) | 2016-10-05 |
| CA2932059A1 (en) | 2015-06-04 |
| IL245865A0 (en) | 2016-07-31 |
| EP3073999B1 (en) | 2018-05-30 |
| AU2014354728A1 (en) | 2016-06-16 |
| JP6483126B2 (ja) | 2019-03-13 |
| US9751889B2 (en) | 2017-09-05 |
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