JP2014521726A5 - - Google Patents
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- JP2014521726A5 JP2014521726A5 JP2014525188A JP2014525188A JP2014521726A5 JP 2014521726 A5 JP2014521726 A5 JP 2014521726A5 JP 2014525188 A JP2014525188 A JP 2014525188A JP 2014525188 A JP2014525188 A JP 2014525188A JP 2014521726 A5 JP2014521726 A5 JP 2014521726A5
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- Prior art keywords
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- 150000001875 compounds Chemical class 0.000 claims description 56
- 238000000034 method Methods 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000012453 solvate Substances 0.000 claims description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 3
- 230000008025 crystallization Effects 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 claims description 2
- 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 239000007787 solid Substances 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 238000001953 recrystallisation Methods 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000002002 slurry Substances 0.000 claims 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000007788 liquid Substances 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- XTEGVFVZDVNBPF-UHFFFAOYSA-N naphthalene-1,5-disulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1S(O)(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-N 0.000 description 4
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229910052805 deuterium Inorganic materials 0.000 description 3
- 125000004431 deuterium atom Chemical group 0.000 description 3
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- HSARCAKRDFJMNW-UHFFFAOYSA-N 1-aminoethanesulfonic acid;2-aminoethanesulfonic acid Chemical compound CC(N)S(O)(=O)=O.NCCS(O)(=O)=O HSARCAKRDFJMNW-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical group OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940116298 l- malic acid Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098895 maleic acid Drugs 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201161522624P | 2011-08-11 | 2011-08-11 | |
| US61/522,624 | 2011-08-11 | ||
| PCT/US2012/050453 WO2013023184A1 (en) | 2011-08-11 | 2012-08-10 | Kinase inhibitor polymorphs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2014521726A JP2014521726A (ja) | 2014-08-28 |
| JP2014521726A5 true JP2014521726A5 (enExample) | 2015-10-01 |
Family
ID=47669006
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014525188A Pending JP2014521726A (ja) | 2011-08-11 | 2012-08-10 | キナーゼ阻害剤多形体 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US20150065524A1 (enExample) |
| EP (1) | EP2741749A4 (enExample) |
| JP (1) | JP2014521726A (enExample) |
| KR (1) | KR20140079368A (enExample) |
| CN (1) | CN103957918A (enExample) |
| AU (1) | AU2012294202B2 (enExample) |
| BR (1) | BR112014003214A2 (enExample) |
| CA (1) | CA2844742A1 (enExample) |
| CL (1) | CL2014000343A1 (enExample) |
| CO (1) | CO6960542A2 (enExample) |
| CR (1) | CR20140082A (enExample) |
| DO (1) | DOP2014000027A (enExample) |
| EA (1) | EA027970B1 (enExample) |
| EC (1) | ECSP14013236A (enExample) |
| HK (1) | HK1199203A1 (enExample) |
| IL (1) | IL230850A0 (enExample) |
| MX (1) | MX2014001662A (enExample) |
| MY (1) | MY186267A (enExample) |
| PE (1) | PE20141358A1 (enExample) |
| PH (1) | PH12014500331A1 (enExample) |
| RU (1) | RU2636588C2 (enExample) |
| SG (2) | SG2014009492A (enExample) |
| TN (1) | TN2014000063A1 (enExample) |
| WO (1) | WO2013023184A1 (enExample) |
| ZA (1) | ZA201401211B (enExample) |
Families Citing this family (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1747747B (zh) | 2003-01-06 | 2012-09-05 | 安吉奥开米公司 | 作为穿过血脑屏障的载体的抑酶肽及类似物 |
| US9365634B2 (en) | 2007-05-29 | 2016-06-14 | Angiochem Inc. | Aprotinin-like polypeptides for delivering agents conjugated thereto to tissues |
| RU2531591C2 (ru) | 2008-10-15 | 2014-10-20 | Ангиокем Инк. | Конъюгаты этопозида и доксорубицина для доставки лекарственных средств |
| US8921314B2 (en) | 2008-10-15 | 2014-12-30 | Angiochem, Inc. | Conjugates of GLP-1 agonists and uses thereof |
| MX2011005963A (es) | 2008-12-05 | 2011-09-01 | Angiochem Inc | Conjugados de neurotensina o analogos de neurotensina y sus usos. |
| CN102300987A (zh) | 2008-12-17 | 2011-12-28 | 安吉奥开米公司 | 膜型-1基质金属蛋白抑制剂及其用途 |
| AU2010239069B2 (en) | 2009-04-20 | 2015-05-14 | Angiochem Inc | Treatment of ovarian cancer using an anticancer agent conjugated to an Angiopep-2 analog |
| MX2012000016A (es) | 2009-07-02 | 2012-03-26 | Angiochem Inc | Conjugados de peptidos multimericos y sus usos. |
| CN106924741A (zh) * | 2011-11-08 | 2017-07-07 | 因特利凯有限责任公司 | 使用多种药剂的治疗方案 |
| CN104250250A (zh) * | 2013-06-25 | 2014-12-31 | 苏州科捷生物医药有限公司 | 4-芳香胺基嘧啶类化合物及其抗肿瘤用途 |
| CN105899232A (zh) | 2013-11-13 | 2016-08-24 | 诺华股份有限公司 | 用于增强免疫应答的mTOR抑制剂 |
| CA2931684C (en) | 2013-12-19 | 2024-02-20 | Novartis Ag | Human mesothelin chimeric antigen receptors and uses thereof |
| EP3087101B1 (en) | 2013-12-20 | 2024-06-05 | Novartis AG | Regulatable chimeric antigen receptor |
| EP3593812A3 (en) | 2014-03-15 | 2020-05-27 | Novartis AG | Treatment of cancer using chimeric antigen receptor |
| IL322264A (en) | 2014-04-07 | 2025-09-01 | Novartis Ag | Cancer treatment using chimeric antigen receptor (CAR) against CD19 |
| US11542488B2 (en) | 2014-07-21 | 2023-01-03 | Novartis Ag | Sortase synthesized chimeric antigen receptors |
| WO2016014530A1 (en) | 2014-07-21 | 2016-01-28 | Novartis Ag | Combinations of low, immune enhancing. doses of mtor inhibitors and cars |
| US9777061B2 (en) | 2014-07-21 | 2017-10-03 | Novartis Ag | Treatment of cancer using a CD33 chimeric antigen receptor |
| US20170209492A1 (en) | 2014-07-31 | 2017-07-27 | Novartis Ag | Subset-optimized chimeric antigen receptor-containing t-cells |
| WO2016025880A1 (en) | 2014-08-14 | 2016-02-18 | Novartis Ag | Treatment of cancer using gfr alpha-4 chimeric antigen receptor |
| SG11201700770PA (en) | 2014-08-19 | 2017-03-30 | Novartis Ag | Anti-cd123 chimeric antigen receptor (car) for use in cancer treatment |
| ES2891332T3 (es) | 2014-09-17 | 2022-01-27 | Novartis Ag | Direccionamiento a células citotóxicas con receptores quiméricos para la inmunoterapia adoptiva |
| AU2015330898B2 (en) | 2014-10-08 | 2022-03-10 | Novartis Ag | Biomarkers predictive of therapeutic responsiveness to chimeric antigen receptor therapy and uses thereof |
| EP3280795B1 (en) | 2015-04-07 | 2021-03-24 | Novartis AG | Combination of chimeric antigen receptor therapy and amino pyrimidine derivatives |
| AU2016249005B2 (en) | 2015-04-17 | 2022-06-16 | Novartis Ag | Methods for improving the efficacy and expansion of chimeric antigen receptor-expressing cells |
| EP3286211A1 (en) | 2015-04-23 | 2018-02-28 | Novartis AG | Treatment of cancer using chimeric antigen receptor and protein kinase a blocker |
| US10980892B2 (en) | 2015-06-15 | 2021-04-20 | Angiochem Inc. | Methods for the treatment of leptomeningeal carcinomatosis |
| ES2636646B1 (es) * | 2016-04-05 | 2018-08-03 | Universidade De Santiago De Compostela | NUEVOS VEHÍCULOS PARA LA TRANSFECCIÓN DE miRNAs |
| CN109641947B (zh) | 2016-07-20 | 2023-04-14 | 犹他大学研究基金会 | Cd229 car t细胞及其使用方法 |
| WO2018067992A1 (en) | 2016-10-07 | 2018-04-12 | Novartis Ag | Chimeric antigen receptors for the treatment of cancer |
| KR20190084310A (ko) | 2016-11-23 | 2019-07-16 | 바이엘 크롭사이언스 악티엔게젤샤프트 | 살충제로서의 2-[3-(알킬술포닐)-2H-인다졸-2-일]-3H-이미다조[4,5-b]피리딘 유도체 및 유사한 화합물 |
| US20200055948A1 (en) | 2017-04-28 | 2020-02-20 | Novartis Ag | Cells expressing a bcma-targeting chimeric antigen receptor, and combination therapy with a gamma secretase inhibitor |
| BR112020013794B1 (pt) * | 2018-01-09 | 2023-05-02 | Halcyon Labs Private Limited | Processo para a preparação de crisaborola de fórmula (i), compostos, uso de um composto de fórmula (iv), (iii) ou (ii), processo para a preparação de crisaborola altamente pura e sal |
| EP3784351A1 (en) | 2018-04-27 | 2021-03-03 | Novartis AG | Car t cell therapies with enhanced efficacy |
| EP3788369A1 (en) | 2018-05-01 | 2021-03-10 | Novartis Ag | Biomarkers for evaluating car-t cells to predict clinical outcome |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW444018B (en) * | 1992-12-17 | 2001-07-01 | Pfizer | Pyrazolopyrimidines |
| US7420084B2 (en) * | 2002-07-18 | 2008-09-02 | Teva Pharmaceutical Industries Ltd. | Polymorphic forms of nateglinide |
| US8476282B2 (en) * | 2008-11-03 | 2013-07-02 | Intellikine Llc | Benzoxazole kinase inhibitors and methods of use |
| AU2012205669B2 (en) * | 2011-01-10 | 2015-08-20 | Infinity Pharmaceuticals Inc. | Processes for preparing isoquinolinones and solid forms of isoquinolinones |
-
2012
- 2012-08-10 RU RU2014109023A patent/RU2636588C2/ru active
- 2012-08-10 PE PE2014000191A patent/PE20141358A1/es not_active Application Discontinuation
- 2012-08-10 WO PCT/US2012/050453 patent/WO2013023184A1/en not_active Ceased
- 2012-08-10 PH PH1/2014/500331A patent/PH12014500331A1/en unknown
- 2012-08-10 CN CN201280043863.6A patent/CN103957918A/zh active Pending
- 2012-08-10 EP EP12821708.0A patent/EP2741749A4/en not_active Withdrawn
- 2012-08-10 CA CA2844742A patent/CA2844742A1/en not_active Abandoned
- 2012-08-10 JP JP2014525188A patent/JP2014521726A/ja active Pending
- 2012-08-10 HK HK14112711.7A patent/HK1199203A1/xx unknown
- 2012-08-10 SG SG2014009492A patent/SG2014009492A/en unknown
- 2012-08-10 MX MX2014001662A patent/MX2014001662A/es unknown
- 2012-08-10 BR BR112014003214A patent/BR112014003214A2/pt not_active Application Discontinuation
- 2012-08-10 KR KR1020147006105A patent/KR20140079368A/ko not_active Ceased
- 2012-08-10 AU AU2012294202A patent/AU2012294202B2/en active Active
- 2012-08-10 MY MYPI2014000363A patent/MY186267A/en unknown
- 2012-08-10 SG SG10201606288TA patent/SG10201606288TA/en unknown
- 2012-08-10 EA EA201490446A patent/EA027970B1/ru not_active IP Right Cessation
- 2012-08-10 US US14/238,426 patent/US20150065524A1/en not_active Abandoned
-
2014
- 2014-02-06 IL IL230850A patent/IL230850A0/en unknown
- 2014-02-10 DO DO2014000027A patent/DOP2014000027A/es unknown
- 2014-02-11 CL CL2014000343A patent/CL2014000343A1/es unknown
- 2014-02-11 TN TNP2014000063A patent/TN2014000063A1/en unknown
- 2014-02-18 ZA ZA2014/01211A patent/ZA201401211B/en unknown
- 2014-02-20 CR CR20140082A patent/CR20140082A/es unknown
- 2014-03-11 EC ECSP14013236 patent/ECSP14013236A/es unknown
- 2014-03-11 CO CO14051879A patent/CO6960542A2/es unknown
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