JP2013522325A5 - - Google Patents
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- Publication number
- JP2013522325A5 JP2013522325A5 JP2013500246A JP2013500246A JP2013522325A5 JP 2013522325 A5 JP2013522325 A5 JP 2013522325A5 JP 2013500246 A JP2013500246 A JP 2013500246A JP 2013500246 A JP2013500246 A JP 2013500246A JP 2013522325 A5 JP2013522325 A5 JP 2013522325A5
- Authority
- JP
- Japan
- Prior art keywords
- cancer
- composition
- furan
- acetyl
- 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.)
- Granted
Links
- 206010028980 Neoplasm Diseases 0.000 claims description 48
- 201000011510 cancer Diseases 0.000 claims description 48
- DPHUWDIXHNQOSY-UHFFFAOYSA-N napabucasin Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1OC(C(=O)C)=C2 DPHUWDIXHNQOSY-UHFFFAOYSA-N 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 43
- 239000002245 particle Substances 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- 238000002441 X-ray diffraction Methods 0.000 claims description 16
- 238000005481 NMR spectroscopy Methods 0.000 claims description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 238000004128 high performance liquid chromatography Methods 0.000 claims description 13
- 230000001186 cumulative effect Effects 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000012535 impurity Substances 0.000 claims description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 9
- FHRKNQJXHSDMGJ-UHFFFAOYSA-N 3,4-dibromobut-3-en-2-one Chemical compound CC(=O)C(Br)=CBr FHRKNQJXHSDMGJ-UHFFFAOYSA-N 0.000 claims description 8
- AGHIQBRPBAHPMV-UHFFFAOYSA-N 3-bromobut-3-en-2-one Chemical compound CC(=O)C(Br)=C AGHIQBRPBAHPMV-UHFFFAOYSA-N 0.000 claims description 8
- 206010006187 Breast cancer Diseases 0.000 claims description 8
- 208000026310 Breast neoplasm Diseases 0.000 claims description 8
- 206010052360 Colorectal adenocarcinoma Diseases 0.000 claims description 8
- 206010033128 Ovarian cancer Diseases 0.000 claims description 8
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 8
- 235000019439 ethyl acetate Nutrition 0.000 claims description 8
- CSFWPUWCSPOLJW-UHFFFAOYSA-N lawsone Chemical compound C1=CC=C2C(=O)C(O)=CC(=O)C2=C1 CSFWPUWCSPOLJW-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 102000004495 STAT3 Transcription Factor Human genes 0.000 claims description 7
- 108010017324 STAT3 Transcription Factor Proteins 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 208000037819 metastatic cancer Diseases 0.000 claims description 5
- 208000011575 metastatic malignant neoplasm Diseases 0.000 claims description 5
- 201000003076 Angiosarcoma Diseases 0.000 claims description 4
- 208000001258 Hemangiosarcoma Diseases 0.000 claims description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 206010038111 Recurrent cancer Diseases 0.000 claims description 4
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 claims description 4
- 238000007256 debromination reaction Methods 0.000 claims description 4
- 201000006585 gastric adenocarcinoma Diseases 0.000 claims description 4
- 201000010536 head and neck cancer Diseases 0.000 claims description 4
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 4
- 201000005202 lung cancer Diseases 0.000 claims description 4
- 208000020816 lung neoplasm Diseases 0.000 claims description 4
- 201000001441 melanoma Diseases 0.000 claims description 4
- 230000002018 overexpression Effects 0.000 claims description 4
- 239000000651 prodrug Substances 0.000 claims description 3
- 229940002612 prodrug Drugs 0.000 claims description 3
- 239000013557 residual solvent Substances 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- KUJTUBMARVZCNB-UHFFFAOYSA-N 1-(4,9-dihydrobenzo[f][1]benzofuran-2-yl)ethanone Chemical compound C(C)(=O)C1=CC2=C(O1)CC1=CC=CC=C1C2 KUJTUBMARVZCNB-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 230000004083 survival effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 238000002560 therapeutic procedure Methods 0.000 claims 2
- MOMFXATYAINJML-UHFFFAOYSA-N 2-Acetylthiazole Chemical group CC(=O)C1=NC=CS1 MOMFXATYAINJML-UHFFFAOYSA-N 0.000 claims 1
- 102000054765 polymorphisms of proteins Human genes 0.000 claims 1
- 238000000034 method Methods 0.000 description 23
- MFMVRILBADIIJO-UHFFFAOYSA-N benzo[e][1]benzofuran Chemical class C1=CC=C2C(C=CO3)=C3C=CC2=C1 MFMVRILBADIIJO-UHFFFAOYSA-N 0.000 description 8
- 210000004027 cell Anatomy 0.000 description 3
- 206010070308 Refractory cancer Diseases 0.000 description 2
- 208000016691 refractory malignant neoplasm Diseases 0.000 description 2
- 210000000130 stem cell Anatomy 0.000 description 2
- 229940124639 Selective inhibitor Drugs 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31588610P | 2010-03-19 | 2010-03-19 | |
| US31589010P | 2010-03-19 | 2010-03-19 | |
| US61/315,890 | 2010-03-19 | ||
| US61/315,886 | 2010-03-19 | ||
| US32581410P | 2010-04-19 | 2010-04-19 | |
| US61/325,814 | 2010-04-19 | ||
| PCT/US2011/029281 WO2011116398A1 (en) | 2010-03-19 | 2011-03-21 | Novel compounds and compositions for targeting cancer stem cells |
Related Child Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014040227A Division JP2014098050A (ja) | 2010-03-19 | 2014-03-03 | がん幹細胞を標的とするための新規の化合物および組成物 |
| JP2014040226A Division JP2014098049A (ja) | 2010-03-19 | 2014-03-03 | がん幹細胞を標的とするための新規の化合物および組成物 |
| JP2014040225A Division JP5993390B2 (ja) | 2010-03-19 | 2014-03-03 | がん幹細胞を標的とするための新規の化合物および組成物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013522325A JP2013522325A (ja) | 2013-06-13 |
| JP2013522325A5 true JP2013522325A5 (OSRAM) | 2013-12-05 |
| JP5602935B2 JP5602935B2 (ja) | 2014-10-08 |
Family
ID=47678419
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013500246A Expired - Fee Related JP5602935B2 (ja) | 2010-03-19 | 2011-03-21 | がん幹細胞を標的とするための新規の化合物および組成物 |
Country Status (15)
| Country | Link |
|---|---|
| US (4) | US9084766B2 (OSRAM) |
| EP (1) | EP2547334B1 (OSRAM) |
| JP (1) | JP5602935B2 (OSRAM) |
| KR (2) | KR101714819B1 (OSRAM) |
| CN (3) | CN107721958B (OSRAM) |
| AU (2) | AU2011227022C1 (OSRAM) |
| BR (2) | BR112012023661A2 (OSRAM) |
| CA (2) | CA2946899C (OSRAM) |
| DK (1) | DK2547334T3 (OSRAM) |
| ES (1) | ES2659541T3 (OSRAM) |
| MX (2) | MX370721B (OSRAM) |
| NZ (1) | NZ602328A (OSRAM) |
| RU (1) | RU2571661C2 (OSRAM) |
| SG (1) | SG184063A1 (OSRAM) |
| WO (1) | WO2011116398A1 (OSRAM) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5688840B2 (ja) | 2007-09-10 | 2015-03-25 | ボストン バイオメディカル， インコーポレイテッド | 新規のＳｔａｔ３経路阻害剤及び癌幹細胞阻害剤 |
| WO2011116398A1 (en) * | 2010-03-19 | 2011-09-22 | Boston Biomedical, Inc. | Novel compounds and compositions for targeting cancer stem cells |
| SG10201502079VA (en) * | 2010-03-19 | 2015-06-29 | Boston Biomedical Inc | Novel compounds and compositions for targeting cancer stem cells |
| MX2015014181A (es) | 2013-04-09 | 2016-05-24 | Boston Biomedical Inc | 2-acetilnafto [2,3-b]furano -4,9-diona para uso en el tratamiento del cáncer. |
| JP6695275B2 (ja) | 2014-02-07 | 2020-05-20 | ボストン バイオメディカル， インコーポレイテッド | ３−置換カルボニル−ナフト［２，３−ｂ］フラン誘導体又はその薬学的に許容される塩 |
| ES2792851T3 (es) * | 2014-06-09 | 2020-11-12 | Kyoto Pharma Ind | Derivados de naftofurano para uso como agentes antineoplásicos |
| CN107666906A (zh) | 2015-04-17 | 2018-02-06 | 波士顿生物医药有限公司 | 用于治疗癌症的方法 |
| JP2018511645A (ja) | 2015-04-17 | 2018-04-26 | ボストン バイオメディカル， インコーポレイテッド | 癌を治療するための方法 |
| US20180140572A1 (en) | 2015-06-03 | 2018-05-24 | Boston Biomedical, Inc. | Compositions comprising a cancer stemness inhibitor and an immunotherapeutic agent for use in treating cancer |
| US10329267B2 (en) | 2015-07-17 | 2019-06-25 | Sumitomo Dainippon Pharma Co., Ltd. | Method for producing 2-acetyl-4H,9H-naphtho[2,3-b]furan-4,9-dione |
| WO2017079864A1 (en) * | 2015-11-12 | 2017-05-18 | Hangzhou Yier Biotech Co., Ltd. | Treatment of cancers related to chronically active ras |
| CA3011800A1 (en) | 2016-01-20 | 2017-08-03 | Boston Biomedical, Inc. | Methods for treating cancer |
| WO2017160978A1 (en) | 2016-03-15 | 2017-09-21 | Boston Biomedical, Inc. | Cell cultures and use thereof |
| WO2018005444A2 (en) | 2016-06-28 | 2018-01-04 | Boston Biomedical, Inc. | Methods for treating cancer |
| WO2018098352A2 (en) | 2016-11-22 | 2018-05-31 | Jun Oishi | Targeting kras induced immune checkpoint expression |
| WO2018102427A1 (en) | 2016-11-29 | 2018-06-07 | Boston Biomedical, Inc. | Naphthofuran derivatives, preparation, and methods of use thereof |
| JP2020512377A (ja) | 2017-03-30 | 2020-04-23 | ボストン バイオメディカル， インコーポレイテッド | がんを処置および／または防止するための組成物 |
| CA3062656A1 (en) | 2017-05-17 | 2018-11-22 | Boston Biomedical, Inc. | Methods for treating cancer |
| US12257227B2 (en) | 2018-10-12 | 2025-03-25 | 1Globe Biomedical Co., Ltd. | Combination solution for treating chemotherapy refractory cancer |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1049490A1 (ru) * | 1982-05-18 | 1983-10-23 | Ордена Трудового Красного Знамени Институт Химии Ан Мсср | (3 @ ,9 @ ,9 @ )-6,6,9 @ -Триметилтранспергидронафто(2,1- @ )фуран,в качестве душистого компонента парфюмерной композиции |
| JPH1121284A (ja) | 1997-06-30 | 1999-01-26 | Kotobuki:Kk | フラノナフトキノン誘導体及びこれを含有する医薬 |
| WO2004026253A2 (en) * | 2002-09-17 | 2004-04-01 | Arqule, Inc. | Novel lapacho compounds and methods of use thereof |
| US20070238770A1 (en) | 2006-04-05 | 2007-10-11 | Bristol-Myers Squibb Company | Process for preparing novel crystalline forms of peliglitazar, novel stable forms produced therein and formulations |
| JP5688840B2 (ja) * | 2007-09-10 | 2015-03-25 | ボストン バイオメディカル， インコーポレイテッド | 新規のＳｔａｔ３経路阻害剤及び癌幹細胞阻害剤 |
| US20100298402A1 (en) | 2007-11-06 | 2010-11-25 | Orchid Research Laboratories Limited | Stilbene derivatives as pstat3/il-6 inhibitors |
| WO2011116398A1 (en) * | 2010-03-19 | 2011-09-22 | Boston Biomedical, Inc. | Novel compounds and compositions for targeting cancer stem cells |
-
2011
- 2011-03-21 WO PCT/US2011/029281 patent/WO2011116398A1/en not_active Ceased
- 2011-03-21 EP EP11757134.9A patent/EP2547334B1/en active Active
- 2011-03-21 NZ NZ602328A patent/NZ602328A/en unknown
- 2011-03-21 KR KR1020127027267A patent/KR101714819B1/ko active Active
- 2011-03-21 AU AU2011227022A patent/AU2011227022C1/en active Active
- 2011-03-21 CA CA2946899A patent/CA2946899C/en not_active Expired - Fee Related
- 2011-03-21 RU RU2012144421/04A patent/RU2571661C2/ru active
- 2011-03-21 KR KR1020167032280A patent/KR101908208B1/ko active Active
- 2011-03-21 CN CN201710665153.1A patent/CN107721958B/zh active Active
- 2011-03-21 DK DK11757134.9T patent/DK2547334T3/en active
- 2011-03-21 CA CA2793526A patent/CA2793526C/en not_active Expired - Fee Related
- 2011-03-21 JP JP2013500246A patent/JP5602935B2/ja not_active Expired - Fee Related
- 2011-03-21 CN CN2011800231072A patent/CN103002890A/zh active Pending
- 2011-03-21 BR BR112012023661-0A patent/BR112012023661A2/pt not_active Application Discontinuation
- 2011-03-21 SG SG2012068102A patent/SG184063A1/en unknown
- 2011-03-21 ES ES11757134.9T patent/ES2659541T3/es active Active
- 2011-03-21 CN CN201710613671.9A patent/CN107375260B/zh active Active
- 2011-03-21 US US13/634,676 patent/US9084766B2/en not_active Expired - Fee Related
- 2011-03-21 BR BR122021025776-0A patent/BR122021025776B1/pt active IP Right Grant
- 2011-03-21 MX MX2012010434A patent/MX370721B/es active IP Right Grant
- 2011-03-21 MX MX2019001996A patent/MX394137B/es unknown
-
2015
- 2015-03-10 US US14/642,931 patent/US9381184B2/en not_active Expired - Fee Related
-
2016
- 2016-02-15 AU AU2016200953A patent/AU2016200953B2/en active Active
- 2016-05-31 US US15/169,315 patent/US20160271099A1/en not_active Abandoned
-
2018
- 2018-01-05 US US15/863,132 patent/US20180193303A1/en not_active Abandoned
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