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
- Authority
- 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.)
- Granted
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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 (enExample) | 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 (enExample) |
| EP (1) | EP2427467B1 (enExample) |
| JP (3) | JP6000122B2 (enExample) |
| KR (1) | KR101821823B1 (enExample) |
| CN (1) | CN102596977B (enExample) |
| AU (1) | AU2010245669B2 (enExample) |
| BR (1) | BRPI1014802B8 (enExample) |
| CA (2) | CA2964631A1 (enExample) |
| DK (1) | DK2427467T3 (enExample) |
| EA (1) | EA021135B1 (enExample) |
| ES (1) | ES2552163T3 (enExample) |
| MX (1) | MX2011011776A (enExample) |
| MY (1) | MY160392A (enExample) |
| PL (1) | PL2427467T3 (enExample) |
| PT (1) | PT2427467E (enExample) |
| SG (1) | SG175885A1 (enExample) |
| WO (1) | WO2010129918A1 (enExample) |
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 |
| RS58781B1 (sr) | 2012-08-23 | 2019-06-28 | Senestech Inc | Kompozicije i postupci za redukciju reproduktivnog kapaciteta ženki pacova |
| 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 |
| DK3348276T3 (da) * | 2015-09-11 | 2021-08-09 | Ys Ac Co Ltd | Cancerbehandlingssammensætning, hvor af anti-CD26-antistof og et andet anticancermiddel er kombineret |
| 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 |
| WO2021221179A1 (ja) * | 2020-04-28 | 2021-11-04 | 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 |
| US20230303618A1 (en) | 2020-08-21 | 2023-09-28 | Reyoung Corporation | Triptolide conjugates and uses thereof |
| 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 |
| WO2024186320A1 (en) | 2023-03-09 | 2024-09-12 | Minneamrita Therapeutics Llc | Drug combination for treatment of pancreatic cancer |
| WO2024187139A1 (en) | 2023-03-09 | 2024-09-12 | Minneamrita Therapeutics Llc | Drug combination for treatment of gastric cancer |
| AU2024204522B1 (en) | 2023-03-09 | 2024-08-22 | Minneamrita Therapeutics Llc | Drug combination for treatment of gastric 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 |
| US6548537B1 (en) * | 1998-09-02 | 2003-04-15 | Pharmagenesis, Inc. | Triptolide prodrugs having high aqueous solubility |
| DE69932649T2 (de) | 1998-09-02 | 2007-08-09 | Pharmagenesis, Inc., Palo Alto | Triptolid-Prodrugs mit hoher Wasserlöslichkeit |
| 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 |
| AU5368699A (en) | 1999-04-16 | 2000-11-02 | 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 |
| US6569893B2 (en) * | 2001-03-15 | 2003-05-27 | Pharmagenesis, Inc. | Amino acid derivatives of triptolide compounds as immune modulators and anticancer agents |
| CA2470423C (en) * | 2001-12-21 | 2011-03-15 | Guilford Pharmaceuticals, Inc. | Process for preparing water-soluble phosphonooxymethyl derivatives of alcohol and phenol |
| JP4680589B2 (ja) * | 2002-05-31 | 2011-05-11 | ファーマジェネシス， インコーポレイテッド | アポトーシスおよび免疫抑制の調節のためのトリプトリド誘導体 |
| 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 |
| DK1732536T3 (da) | 2004-03-02 | 2012-06-25 | Pharmagenesis Inc | Tripolidlactonringderivater som immunomodulatorer og anticancermidler |
| WO2006012204A2 (en) | 2004-06-25 | 2006-02-02 | 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 |
| CA2658793A1 (en) * | 2006-07-25 | 2008-02-07 | Daniel Dumas | Quinoline derivatives |
| CN101622263B (zh) * | 2007-03-06 | 2013-05-29 | 卫材R&D管理有限公司 | 稳定性被改善的含有磷酸氯甲酯衍生物的组合物及其制备方法 |
| 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 CN CN201080031839.1A patent/CN102596977B/zh active Active
- 2010-05-07 CA CA2964631A patent/CA2964631A1/en not_active Abandoned
- 2010-05-07 SG SG2011081122A patent/SG175885A1/en unknown
- 2010-05-07 JP JP2012510027A patent/JP6000122B2/ja active Active
- 2010-05-07 CA CA2760953A patent/CA2760953C/en active Active
- 2010-05-07 EA EA201190293A patent/EA021135B1/ru unknown
- 2010-05-07 DK DK10719188.4T patent/DK2427467T3/en active
- 2010-05-07 AU AU2010245669A patent/AU2010245669B2/en active Active
- 2010-05-07 WO PCT/US2010/034117 patent/WO2010129918A1/en not_active Ceased
- 2010-05-07 US US13/319,316 patent/US8507552B2/en active Active
- 2010-05-07 KR KR1020117029123A patent/KR101821823B1/ko active Active
- 2010-05-07 PT PT107191884T patent/PT2427467E/pt unknown
- 2010-05-07 BR BRPI1014802A patent/BRPI1014802B8/pt active IP Right Grant
- 2010-05-07 MY MYPI2011005335A patent/MY160392A/en unknown
- 2010-05-07 ES ES10719188.4T patent/ES2552163T3/es active Active
- 2010-05-07 PL PL10719188T patent/PL2427467T3/pl unknown
- 2010-05-07 MX MX2011011776A patent/MX2011011776A/es active IP Right Grant
-
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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