JP2012526148A5 - - Google Patents
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- JP2012526148A5 JP2012526148A5 JP2012510027A JP2012510027A JP2012526148A5 JP 2012526148 A5 JP2012526148 A5 JP 2012526148A5 JP 2012510027 A JP2012510027 A JP 2012510027A JP 2012510027 A JP2012510027 A JP 2012510027A JP 2012526148 A5 JP2012526148 A5 JP 2012526148A5
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- JP
- Japan
- Prior art keywords
- compound
- alkyl
- cancer
- formula
- item
- 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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- 150000001875 compounds Chemical class 0.000 claims description 40
- 206010028980 Neoplasm Diseases 0.000 claims description 20
- 201000011510 cancer Diseases 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
- 101710163595 Chaperone protein DnaK Proteins 0.000 claims description 8
- 101710178376 Heat shock 70 kDa protein Proteins 0.000 claims description 8
- 101710152018 Heat shock cognate 70 kDa protein Proteins 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- -1 pyrrolidino, piperidino, piperazino Chemical group 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- ZHBJMVNZRZUQEP-KIKMAQITSA-L minnelide Chemical group [Na+].[Na+].O=C1OCC([C@@H]2C3)=C1CC[C@]2(C)[C@]12O[C@H]1[C@@H]1O[C@]1(C(C)C)[C@@H](OCOP([O-])([O-])=O)[C@]21[C@H]3O1 ZHBJMVNZRZUQEP-KIKMAQITSA-L 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- YKUJZZHGTWVWHA-UHFFFAOYSA-N triptolide Natural products COC12CC3OC3(C(C)C)C(O)C14OC4CC5C6=C(CCC25C)C(=O)OC6 YKUJZZHGTWVWHA-UHFFFAOYSA-N 0.000 claims description 4
- 230000005764 inhibitory process Effects 0.000 claims description 3
- 230000000069 prophylactic effect Effects 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 239000004475 Arginine Substances 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical group NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004471 Glycine Substances 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004472 Lysine Substances 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 claims description 2
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims description 2
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical group OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 2
- 229910052782 aluminium Inorganic materials 0.000 claims description 2
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 229910052788 barium Inorganic materials 0.000 claims description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 150000001767 cationic compounds Chemical class 0.000 claims description 2
- 230000010261 cell growth Effects 0.000 claims description 2
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 claims description 2
- 229960001231 choline Drugs 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910001411 inorganic cation Inorganic materials 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 238000013160 medical therapy Methods 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 150000002892 organic cations Chemical class 0.000 claims description 2
- 229960003104 ornithine Drugs 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical group OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 2
- 229960000281 trometamol Drugs 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 239000011701 zinc Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 5
- 206010029260 Neuroblastoma Diseases 0.000 description 8
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 8
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 description 8
- 201000002528 pancreatic cancer Diseases 0.000 description 8
- 208000008443 pancreatic carcinoma Diseases 0.000 description 8
- 238000000034 method Methods 0.000 description 7
- 206010009944 Colon cancer Diseases 0.000 description 6
- 208000005718 Stomach Neoplasms Diseases 0.000 description 6
- 206010017758 gastric cancer Diseases 0.000 description 6
- 201000011549 stomach cancer Diseases 0.000 description 6
- 206010006187 Breast cancer Diseases 0.000 description 4
- 208000026310 Breast neoplasm Diseases 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- 208000029742 colonic neoplasm Diseases 0.000 description 4
- 208000005017 glioblastoma Diseases 0.000 description 4
- 201000007270 liver cancer Diseases 0.000 description 4
- 208000014018 liver neoplasm Diseases 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 3
- 206010004593 Bile duct cancer Diseases 0.000 description 2
- 206010008342 Cervix carcinoma Diseases 0.000 description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 description 2
- 208000000461 Esophageal Neoplasms Diseases 0.000 description 2
- 208000008839 Kidney Neoplasms Diseases 0.000 description 2
- 206010023774 Large cell lung cancer Diseases 0.000 description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 2
- 206010025323 Lymphomas Diseases 0.000 description 2
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 2
- 206010030155 Oesophageal carcinoma Diseases 0.000 description 2
- 206010033128 Ovarian cancer Diseases 0.000 description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 description 2
- 206010035226 Plasma cell myeloma Diseases 0.000 description 2
- 206010060862 Prostate cancer Diseases 0.000 description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 2
- 206010038389 Renal cancer Diseases 0.000 description 2
- 206010041067 Small cell lung cancer Diseases 0.000 description 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 2
- 208000026900 bile duct neoplasm Diseases 0.000 description 2
- 230000009702 cancer cell proliferation Effects 0.000 description 2
- 201000010881 cervical cancer Diseases 0.000 description 2
- 208000006990 cholangiocarcinoma Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 201000004101 esophageal cancer Diseases 0.000 description 2
- 201000010982 kidney cancer Diseases 0.000 description 2
- 201000005202 lung cancer Diseases 0.000 description 2
- 201000009546 lung large cell carcinoma Diseases 0.000 description 2
- 208000020816 lung neoplasm Diseases 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 201000000050 myeloid neoplasm Diseases 0.000 description 2
- 208000000587 small cell lung carcinoma Diseases 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17624909P | 2009-05-07 | 2009-05-07 | |
| US61/176,249 | 2009-05-07 | ||
| PCT/US2010/034117 WO2010129918A1 (en) | 2009-05-07 | 2010-05-07 | Triptolide prodrugs |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014137661A Division JP2014185181A (ja) | 2009-05-07 | 2014-07-03 | トリプトリド製品 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012526148A JP2012526148A (ja) | 2012-10-25 |
| JP2012526148A5 true JP2012526148A5 (https=) | 2013-06-06 |
| JP6000122B2 JP6000122B2 (ja) | 2016-09-28 |
Family
ID=42244313
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012510027A Active JP6000122B2 (ja) | 2009-05-07 | 2010-05-07 | トリプトリド製品 |
| JP2014137661A Withdrawn JP2014185181A (ja) | 2009-05-07 | 2014-07-03 | トリプトリド製品 |
| JP2016002236A Pending JP2016065099A (ja) | 2009-05-07 | 2016-01-08 | トリプトリド製品 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014137661A Withdrawn JP2014185181A (ja) | 2009-05-07 | 2014-07-03 | トリプトリド製品 |
| JP2016002236A Pending JP2016065099A (ja) | 2009-05-07 | 2016-01-08 | トリプトリド製品 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US8507552B2 (https=) |
| EP (1) | EP2427467B1 (https=) |
| JP (3) | JP6000122B2 (https=) |
| KR (1) | KR101821823B1 (https=) |
| CN (1) | CN102596977B (https=) |
| AU (1) | AU2010245669B2 (https=) |
| BR (1) | BRPI1014802B8 (https=) |
| CA (2) | CA2760953C (https=) |
| DK (1) | DK2427467T3 (https=) |
| EA (1) | EA021135B1 (https=) |
| ES (1) | ES2552163T3 (https=) |
| MX (1) | MX2011011776A (https=) |
| MY (1) | MY160392A (https=) |
| PL (1) | PL2427467T3 (https=) |
| PT (1) | PT2427467E (https=) |
| SG (1) | SG175885A1 (https=) |
| WO (1) | WO2010129918A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9150600B2 (en) | 2009-05-07 | 2015-10-06 | Regents Of The University Of Minnesota | Triptolide prodrugs |
| DK3510860T3 (da) * | 2012-08-23 | 2021-10-18 | Senestech Inc | Nedsættelse af pattedyrs reproduktive kapacitet |
| WO2014047783A1 (zh) * | 2012-09-25 | 2014-04-03 | 鼎泓国际投资（香港）有限公司 | 含有雷公藤甲素及雷公藤甲素类衍生物和Bcl-2抑制剂的药物组合物及其应用 |
| WO2014167581A2 (en) * | 2013-04-01 | 2014-10-16 | Laurus Labs Private Limited | An improved process for the preparation of triptolide prodrugs |
| KR20180061226A (ko) * | 2015-09-11 | 2018-06-07 | 와이즈에이씨가부시키가이샤 | 항cd26 항체와 다른 항암제를 조합한 암 치료용 조성물 |
| CN109942665B (zh) * | 2018-04-02 | 2021-04-06 | 欣凯医药化工中间体（上海）有限公司 | 雷公藤内酯醇衍生物及其制备方法和应用 |
| CN110551171B (zh) * | 2018-05-31 | 2021-07-27 | 欣凯医药化工中间体（上海）有限公司 | 一种雷公藤内酯醇衍生物的制备方法 |
| KR20210058880A (ko) * | 2018-09-13 | 2021-05-24 | 미네암리타 테라퓨틱스, 엘엘씨 | 섬유증, nash, 및 nafld를 치료하기 위한 방법에서 사용을 위한 트립톨리드 및 이의 전구약물 |
| JP7702110B2 (ja) * | 2020-04-28 | 2025-07-03 | 国立大学法人高知大学 | ヒト膵癌オルガノイドを用いたマウスモデルの樹立 |
| CN116583303A (zh) | 2020-08-21 | 2023-08-11 | 瑞阳公司 | 雷公藤甲素缀合物和其用途 |
| CN115227829B (zh) * | 2022-02-22 | 2023-10-13 | 成都中医药大学 | 酸敏感性适配体雷公藤甲素偶联物及应用 |
| KR102821060B1 (ko) | 2023-03-09 | 2025-06-16 | 미네암리타 테라퓨틱스, 엘엘씨 | 위암의 치료를 위한 약물 조합 |
| WO2024187139A1 (en) | 2023-03-09 | 2024-09-12 | Minneamrita Therapeutics Llc | Drug combination for treatment of gastric cancer |
| WO2024186320A1 (en) | 2023-03-09 | 2024-09-12 | Minneamrita Therapeutics Llc | Drug combination for treatment of pancreatic cancer |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5843452A (en) | 1992-11-09 | 1998-12-01 | Pharmagenesis, Inc. | Immunotherapy composition and method |
| US5759550A (en) | 1993-05-06 | 1998-06-02 | Pharmagenesis, Inc. | Method for suppressing xenograft rejection |
| US5609991A (en) | 1995-02-10 | 1997-03-11 | Morton International, Inc. | Photoimageable composition having improved alkaline process resistance and tack-free surface for contact imaging |
| US5663335A (en) | 1996-03-01 | 1997-09-02 | Pharmagenesis, Inc. | Immunosuppressive compounds and methods |
| US5962516A (en) | 1997-02-28 | 1999-10-05 | Pharmagenesis, Inc. | Immunosuppressive compounds and methods |
| US6204257B1 (en) * | 1998-08-07 | 2001-03-20 | Universtiy Of Kansas | Water soluble prodrugs of hindered alcohols |
| CN1316997A (zh) * | 1998-09-02 | 2001-10-10 | 法玛吉尼西斯公司 | 具有高水溶性的雷公藤内酯前药 |
| US6548537B1 (en) * | 1998-09-02 | 2003-04-15 | Pharmagenesis, Inc. | Triptolide prodrugs having high aqueous solubility |
| WO2000048619A1 (en) | 1999-02-16 | 2000-08-24 | The Board Of Trustees Of The Leland Stanford Junior University | Combined therapy of diterpenoid triepoxides and trail for synergistic killing of tumor cells |
| WO2000063212A1 (en) | 1999-04-16 | 2000-10-26 | Chengdu Diao Pharmaceutical Group Company Limited | Derivatives of triptolide, and preparation and uses thereof |
| US6294546B1 (en) | 1999-08-30 | 2001-09-25 | The Broad Of Trustees Of The Leland Stanford Junior University | Uses of diterpenoid triepoxides as an anti-proliferative agent |
| US6620843B2 (en) * | 2001-01-19 | 2003-09-16 | Pharmagenesis | Anticancer treatment using triptolide prodrugs |
| WO2002074759A1 (en) | 2001-03-15 | 2002-09-26 | Pharmagenesis, Inc. | Amino acid derivatives of triptolide compounds as immune modulators and anticancer agent |
| KR101016969B1 (ko) * | 2001-12-21 | 2011-02-25 | 에이자이 아이엔씨. | 알콜 및 페놀의 수용성 포스포노옥시메틸 유도체를제조하는 방법 |
| EP2468277A1 (en) | 2002-05-31 | 2012-06-27 | Pharmagenesis, Inc. | Triptolide derivatives for modulation of apoptosis and immunosuppression |
| CN100398544C (zh) * | 2002-09-18 | 2008-07-02 | 成都达远药物有限公司 | 高免疫抑制活性的水溶性雷公藤内酯醇衍生物及其应用 |
| WO2004058246A1 (en) | 2002-12-17 | 2004-07-15 | Pharmagenesis, Inc. | Triptolide derivatives as immunomodulator and anticancer agents |
| CN1223595C (zh) | 2002-12-27 | 2005-10-19 | 中国科学院上海药物研究所 | 雷公藤内酯醇衍生物及其应用 |
| US6943259B2 (en) | 2003-02-25 | 2005-09-13 | Pharmagenesis, Inc. | Halogenated triptolide derivatives as immunomodulators and anticancer agents |
| WO2005020887A2 (en) | 2003-06-27 | 2005-03-10 | Pharmagenesis, Inc. | Method for treatment of severe acute respiratory syndrome |
| US7820834B2 (en) | 2003-12-24 | 2010-10-26 | Pharmagenesis, Inc. | Triptolide 5,6-derivatives as immunomodulators and anticancer agents |
| JP5252765B2 (ja) | 2003-12-26 | 2013-07-31 | 学校法人東京薬科大学 | 皮脂産生抑制剤及び皮脂腺発達抑制剤、並びに、皮膚外用剤 |
| ES2385716T3 (es) | 2004-03-02 | 2012-07-30 | Pharmagenesis, Inc. | Derivados en el anillo de lactona de triptolida como inmunomoduladores y agentes anticáncer |
| US20070244080A1 (en) | 2004-06-25 | 2007-10-18 | Pharmagenesis, Inc. | Method for Treatment of Inflammatory Disorders Using Triptolide Compounds |
| WO2007025031A2 (en) * | 2005-08-24 | 2007-03-01 | Cephalon, Inc. | Prodrugs of indanone and tetralone compounds |
| CN101049300A (zh) | 2006-04-04 | 2007-10-10 | 中国科学院上海药物研究所 | 包含雷公藤内酯醇衍生物的药物组合物、其剂型和应用 |
| RU2009106461A (ru) * | 2006-07-25 | 2010-08-27 | Энвиво Фармасьютикалз, Инк. (Us) | Хинолиновые производные |
| JP5221514B2 (ja) * | 2007-03-06 | 2013-06-26 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 安定性が改善されたクロロメチルフォスフェイト誘導体を含む組成物及びその製造方法 |
| FI20070574A0 (fi) * | 2007-07-30 | 2007-07-30 | Kuopion Yliopisto | Vesiliukoinen propofolin etylideenifosfaatti-aihiolääke |
| WO2009023201A1 (en) | 2007-08-16 | 2009-02-19 | Myelorx Llc | Rigid derivatives of triptolide as anticancer, immune suppressant, anti-fibrosis, and cns protectant agents |
-
2010
- 2010-05-07 EP EP10719188.4A patent/EP2427467B1/en active Active
- 2010-05-07 MY MYPI2011005335A patent/MY160392A/en unknown
- 2010-05-07 SG SG2011081122A patent/SG175885A1/en unknown
- 2010-05-07 CA CA2760953A patent/CA2760953C/en active Active
- 2010-05-07 PT PT107191884T patent/PT2427467E/pt unknown
- 2010-05-07 MX MX2011011776A patent/MX2011011776A/es active IP Right Grant
- 2010-05-07 BR BRPI1014802A patent/BRPI1014802B8/pt active IP Right Grant
- 2010-05-07 AU AU2010245669A patent/AU2010245669B2/en active Active
- 2010-05-07 PL PL10719188T patent/PL2427467T3/pl unknown
- 2010-05-07 JP JP2012510027A patent/JP6000122B2/ja active Active
- 2010-05-07 CA CA2964631A patent/CA2964631A1/en not_active Abandoned
- 2010-05-07 WO PCT/US2010/034117 patent/WO2010129918A1/en not_active Ceased
- 2010-05-07 CN CN201080031839.1A patent/CN102596977B/zh active Active
- 2010-05-07 ES ES10719188.4T patent/ES2552163T3/es active Active
- 2010-05-07 KR KR1020117029123A patent/KR101821823B1/ko active Active
- 2010-05-07 EA EA201190293A patent/EA021135B1/ru unknown
- 2010-05-07 US US13/319,316 patent/US8507552B2/en active Active
- 2010-05-07 DK DK10719188.4T patent/DK2427467T3/en active
-
2014
- 2014-07-03 JP JP2014137661A patent/JP2014185181A/ja not_active Withdrawn
-
2016
- 2016-01-08 JP JP2016002236A patent/JP2016065099A/ja active Pending
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