JP2013515737A5 - - Google Patents
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- Publication number
- JP2013515737A5 JP2013515737A5 JP2012546161A JP2012546161A JP2013515737A5 JP 2013515737 A5 JP2013515737 A5 JP 2013515737A5 JP 2012546161 A JP2012546161 A JP 2012546161A JP 2012546161 A JP2012546161 A JP 2012546161A JP 2013515737 A5 JP2013515737 A5 JP 2013515737A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolo
- dihydro
- trans
- quinolin
- dione
- 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.)
- Pending
Links
- -1 quinolin-1-yl Chemical group 0.000 claims description 75
- 238000000034 method Methods 0.000 claims description 69
- 239000002904 solvent Substances 0.000 claims description 64
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 51
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
- 239000000243 solution Substances 0.000 claims description 33
- 239000003125 aqueous solvent Substances 0.000 claims description 32
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 27
- UCEQXRCJXIVODC-PMACEKPBSA-N LSM-1131 Chemical compound C1CCC2=CC=CC3=C2N1C=C3[C@@H]1C(=O)NC(=O)[C@H]1C1=CNC2=CC=CC=C12 UCEQXRCJXIVODC-PMACEKPBSA-N 0.000 claims description 27
- 239000012044 organic layer Substances 0.000 claims description 23
- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 claims description 21
- 239000013078 crystal Substances 0.000 claims description 14
- AZRRZGIBBLWSSQ-UHFFFAOYSA-N 4-ethyl-7-phenyl-3,5-diazabicyclo[2.2.2]octane-2,6-dione Chemical compound N1C(=O)C2C(=O)NC1(CC)CC2C1=CC=CC=C1 AZRRZGIBBLWSSQ-UHFFFAOYSA-N 0.000 claims description 12
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 12
- 238000005406 washing Methods 0.000 claims description 12
- 241000551547 Dione <red algae> Species 0.000 claims description 8
- 230000005855 radiation Effects 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 7
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 7
- VNQNEQQYAIPCAQ-UHFFFAOYSA-N 3-(1h-indol-3-yl)pyrrolidine-2,5-dione Chemical compound O=C1NC(=O)CC1C1=CNC2=CC=CC=C12 VNQNEQQYAIPCAQ-UHFFFAOYSA-N 0.000 claims description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 239000012266 salt solution Substances 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 201000011510 cancer Diseases 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- GNFTZDOKVXKIBK-UHFFFAOYSA-N 3-(2-methoxyethoxy)benzohydrazide Chemical compound COCCOC1=CC=CC(C(=O)NN)=C1 GNFTZDOKVXKIBK-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 claims description 4
- 229960003908 pseudoephedrine Drugs 0.000 claims description 4
- 239000002002 slurry Substances 0.000 claims description 4
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 3
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 3
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 3
- 206010006187 Breast cancer Diseases 0.000 claims description 3
- 208000026310 Breast neoplasm Diseases 0.000 claims description 3
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 3
- 206010009944 Colon cancer Diseases 0.000 claims description 3
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 3
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 3
- 206010033128 Ovarian cancer Diseases 0.000 claims description 3
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 3
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 3
- 206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- 206010038389 Renal cancer Diseases 0.000 claims description 3
- 208000029742 colonic neoplasm Diseases 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 3
- 201000005202 lung cancer Diseases 0.000 claims description 3
- 208000020816 lung neoplasm Diseases 0.000 claims description 3
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 201000001441 melanoma Diseases 0.000 claims description 3
- 201000002528 pancreatic cancer Diseases 0.000 claims description 3
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 201000010174 renal carcinoma Diseases 0.000 claims description 3
- 239000011780 sodium chloride Substances 0.000 claims description 3
- AAUMLJXGWCWDPR-FKLPMGAJSA-N (+/-)-trans-3-(5,6-dihydro-4h-pyrrolo[3,2,1-ij]quinolin-1-yl)-4-(1h-indol-3-yl)pyrrolidine-2,5-dione dcm Chemical compound ClCCl.C1CCC2=CC=CC3=C2N1C=C3[C@@H]1C(=O)NC(=O)[C@H]1C1=CNC2=CC=CC=C12 AAUMLJXGWCWDPR-FKLPMGAJSA-N 0.000 claims description 2
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 2
- UKWZRDPRXOROJQ-UHFFFAOYSA-N ClCCl.N1C(CCC1=O)=O Chemical compound ClCCl.N1C(CCC1=O)=O UKWZRDPRXOROJQ-UHFFFAOYSA-N 0.000 claims description 2
- XJARZERVKWKOER-FKLPMGAJSA-N NCCC1CCCCC1.C1CCC2=CC=CC3=C2N1C=C3[C@@H]1C(=O)NC(=O)[C@H]1C1=CNC2=CC=CC=C12 Chemical compound NCCC1CCCCC1.C1CCC2=CC=CC3=C2N1C=C3[C@@H]1C(=O)NC(=O)[C@H]1C1=CNC2=CC=CC=C12 XJARZERVKWKOER-FKLPMGAJSA-N 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims description 2
- 238000007865 diluting Methods 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- AGVKXDPPPSLISR-UHFFFAOYSA-N n-ethylcyclohexanamine Chemical compound CCNC1CCCCC1 AGVKXDPPPSLISR-UHFFFAOYSA-N 0.000 claims description 2
- 238000012856 packing Methods 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000011176 pooling Methods 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 208000006265 Renal cell carcinoma Diseases 0.000 claims 1
- 201000000050 myeloid neoplasm Diseases 0.000 claims 1
- 102000054765 polymorphisms of proteins Human genes 0.000 claims 1
- MVPDOCKVRBYAPQ-RTBURBONSA-N 1-[(3r,4r)-4-(1h-indol-3-yl)-pyrrolidin-3-yl]-5,6-dihydro-4h-pyrrolo[3,2,1-ij]quinoline Chemical compound C1CCC2=CC=CC3=C2N1C=C3[C@@H]1CNC[C@H]1C1=CNC2=CC=CC=C12 MVPDOCKVRBYAPQ-RTBURBONSA-N 0.000 description 10
- 208000034578 Multiple myelomas Diseases 0.000 description 2
- 238000002955 isolation Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28956309P | 2009-12-23 | 2009-12-23 | |
| US61/289,563 | 2009-12-23 | ||
| PCT/US2010/061625 WO2011079142A2 (en) | 2009-12-23 | 2010-12-21 | Purified pyrroloquinolinyl-pyrrolidine-2,5-dione compositions and methods for preparing and using same |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015198998A Division JP2016041712A (ja) | 2009-12-23 | 2015-10-07 | 精製されたピロロキノリニル−ピロリジン−２，５−ジオン組成物ならびにその調製方法および使用方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013515737A JP2013515737A (ja) | 2013-05-09 |
| JP2013515737A5 true JP2013515737A5 (https=) | 2014-02-06 |
Family
ID=44188284
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012546161A Pending JP2013515737A (ja) | 2009-12-23 | 2010-12-21 | 精製されたピロロキノリニル−ピロリジン−２，５−ジオン組成物ならびにその調製方法および使用方法 |
| JP2015198998A Pending JP2016041712A (ja) | 2009-12-23 | 2015-10-07 | 精製されたピロロキノリニル−ピロリジン−２，５−ジオン組成物ならびにその調製方法および使用方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015198998A Pending JP2016041712A (ja) | 2009-12-23 | 2015-10-07 | 精製されたピロロキノリニル−ピロリジン−２，５−ジオン組成物ならびにその調製方法および使用方法 |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US8552192B2 (https=) |
| EP (2) | EP2515904A4 (https=) |
| JP (2) | JP2013515737A (https=) |
| KR (2) | KR20160121602A (https=) |
| CN (2) | CN104910159A (https=) |
| AU (2) | AU2010336533B9 (https=) |
| BR (1) | BR112012015656A2 (https=) |
| CA (1) | CA2785503A1 (https=) |
| CO (1) | CO6561823A2 (https=) |
| HK (1) | HK1215025A1 (https=) |
| MX (1) | MX2012007259A (https=) |
| MY (2) | MY156701A (https=) |
| NZ (2) | NZ628087A (https=) |
| PH (2) | PH12012501293A1 (https=) |
| RU (1) | RU2556205C2 (https=) |
| SG (1) | SG181927A1 (https=) |
| TW (3) | TWI506026B (https=) |
| WO (1) | WO2011079142A2 (https=) |
| ZA (1) | ZA201204759B (https=) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100941205B1 (ko) * | 2005-02-09 | 2010-02-10 | 아르퀼 인코포레이티드 | 말레이미드 유도체, 약제학적 조성물 및 암을 치료하는방법 |
| MY156701A (en) * | 2009-12-23 | 2016-03-15 | Arqule Inc | Purified pyrroloquinolinyl-pyrrolidine-2,5-dione compositions and methods for preparing and using same |
| TW201315470A (zh) * | 2011-07-07 | 2013-04-16 | Arqule Inc | 吡咯並喹啉基－吡咯啶－２，５－二酮調製劑類及製備和使用彼等之方法 |
| WO2013162714A1 (en) * | 2012-04-23 | 2013-10-31 | Arqule, Inc. | Highly pure pyrroloquinolinyl-pyrrole-2,5-dione and pyrroloquinolinyl-pyrrolidine-2,5-dione and methods of preparing same |
| EP3021849B1 (en) * | 2013-07-16 | 2019-10-09 | Dr. Reddy's Laboratories Ltd. | Novel crystalline forms of pemetrexed tromethamine salts |
| CN111247153B (zh) * | 2017-08-11 | 2024-04-02 | 开动疗法公司 | 3-(5-氟苯并呋喃-3-基)-4-(5-甲基-5H-[1，3]间二氧杂环戊烯并[4，5-f]吲哚-7-基)吡咯-2，5-二酮的固体形式 |
| CN110806454A (zh) * | 2018-08-06 | 2020-02-18 | 江苏正大清江制药有限公司 | 一种盐酸吉西他滨中手性异构体的检测方法 |
| EA202192575A1 (ru) | 2019-03-21 | 2022-01-14 | Онксео | Соединения dbait в сочетании с ингибиторами киназ для лечения рака |
| CN114761006A (zh) | 2019-11-08 | 2022-07-15 | Inserm(法国国家健康医学研究院) | 对激酶抑制剂产生耐药性的癌症的治疗方法 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| WO2022216870A1 (en) * | 2021-04-07 | 2022-10-13 | Ur-1 Therapeutics, Inc. | Urat1 inhibitor, pharmaceutical compositions and uses thereof |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4522811A (en) | 1982-07-08 | 1985-06-11 | Syntex (U.S.A.) Inc. | Serial injection of muramyldipeptides and liposomes enhances the anti-infective activity of muramyldipeptides |
| DE4128015A1 (de) * | 1991-08-23 | 1993-02-25 | Kali Chemie Pharma Gmbh | 1,7-anellierte 2-(piperazinoalkyl)indol-derivate sowie verfahren und zwischenprodukte zu ihrer herstellung und diese verbindugnen enthaltende arzneimittel |
| US5760237A (en) * | 1995-08-25 | 1998-06-02 | California Institute Of Technology | Synthesis of l-azatyrosine using pseudoephedrine as a chiral auxiliary |
| EP1242420A2 (en) * | 1999-12-16 | 2002-09-25 | Eli Lilly And Company | Agents and methods for the treatment of proliferative diseases |
| ATE315017T1 (de) * | 2002-07-31 | 2006-02-15 | Firmenich & Cie | Verfahren zur racematspaltung einer sclareolid- vorstufe |
| CA2573508A1 (en) * | 2004-09-10 | 2006-03-23 | Wyeth | Process for the scalable synthesis of 1, 3, 4, 9-tetrahydropyrano[3, 4-b]-indole derivatives |
| KR100941205B1 (ko) * | 2005-02-09 | 2010-02-10 | 아르퀼 인코포레이티드 | 말레이미드 유도체, 약제학적 조성물 및 암을 치료하는방법 |
| US20070185346A1 (en) * | 2006-02-03 | 2007-08-09 | Vaidya Niteen A | Kit for automated resolving agent selection and method thereof |
| EP2170870B1 (en) | 2007-06-22 | 2014-03-05 | ArQule, Inc. | Pyrrolidinone, pyrrolidine-2, 5-dione, pyrrolidine and thiosuccinimide derivatives, compositions and methods for treatment of cancer |
| CA2912546A1 (en) * | 2007-06-22 | 2008-12-31 | Arqule, Inc. | Compositions and methods for treatment of cancer |
| MY156701A (en) * | 2009-12-23 | 2016-03-15 | Arqule Inc | Purified pyrroloquinolinyl-pyrrolidine-2,5-dione compositions and methods for preparing and using same |
| WO2013162714A1 (en) * | 2012-04-23 | 2013-10-31 | Arqule, Inc. | Highly pure pyrroloquinolinyl-pyrrole-2,5-dione and pyrroloquinolinyl-pyrrolidine-2,5-dione and methods of preparing same |
-
2010
- 2010-12-21 MY MYPI2012002895A patent/MY156701A/en unknown
- 2010-12-21 KR KR1020167027918A patent/KR20160121602A/ko not_active Ceased
- 2010-12-21 PH PH1/2012/501293A patent/PH12012501293A1/en unknown
- 2010-12-21 SG SG2012047023A patent/SG181927A1/en unknown
- 2010-12-21 EP EP10840083.9A patent/EP2515904A4/en not_active Ceased
- 2010-12-21 CN CN201510243421.1A patent/CN104910159A/zh active Pending
- 2010-12-21 RU RU2012131344/04A patent/RU2556205C2/ru active
- 2010-12-21 MY MYPI2014003506A patent/MY169232A/en unknown
- 2010-12-21 NZ NZ628087A patent/NZ628087A/en unknown
- 2010-12-21 JP JP2012546161A patent/JP2013515737A/ja active Pending
- 2010-12-21 BR BR112012015656A patent/BR112012015656A2/pt not_active IP Right Cessation
- 2010-12-21 EP EP16168527.6A patent/EP3081567A3/en not_active Withdrawn
- 2010-12-21 NZ NZ600800A patent/NZ600800A/en unknown
- 2010-12-21 KR KR1020127019155A patent/KR101669707B1/ko active Active
- 2010-12-21 CA CA2785503A patent/CA2785503A1/en not_active Abandoned
- 2010-12-21 AU AU2010336533A patent/AU2010336533B9/en active Active
- 2010-12-21 MX MX2012007259A patent/MX2012007259A/es unknown
- 2010-12-21 CN CN201080064457.9A patent/CN102834097B/zh active Active
- 2010-12-21 WO PCT/US2010/061625 patent/WO2011079142A2/en not_active Ceased
- 2010-12-22 US US12/975,644 patent/US8552192B2/en active Active
- 2010-12-22 TW TW099145242A patent/TWI506026B/zh active
- 2010-12-22 TW TW104125790A patent/TWI557125B/zh active
- 2010-12-22 TW TW105127477A patent/TW201643163A/zh unknown
-
2012
- 2012-06-26 ZA ZA2012/04759A patent/ZA201204759B/en unknown
- 2012-07-23 CO CO12122679A patent/CO6561823A2/es active IP Right Grant
-
2013
- 2013-09-25 US US14/036,672 patent/US8871933B2/en active Active
-
2014
- 2014-02-06 PH PH12014500310A patent/PH12014500310A1/en unknown
- 2014-09-26 US US14/498,651 patent/US9499540B2/en active Active
-
2015
- 2015-10-07 JP JP2015198998A patent/JP2016041712A/ja active Pending
- 2015-10-14 AU AU2015243015A patent/AU2015243015B2/en active Active
-
2016
- 2016-03-16 HK HK16103027.3A patent/HK1215025A1/zh unknown
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