JP2016515530A5 - - Google Patents
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- Publication number
- JP2016515530A5 JP2016515530A5 JP2016503315A JP2016503315A JP2016515530A5 JP 2016515530 A5 JP2016515530 A5 JP 2016515530A5 JP 2016503315 A JP2016503315 A JP 2016503315A JP 2016503315 A JP2016503315 A JP 2016503315A JP 2016515530 A5 JP2016515530 A5 JP 2016515530A5
- Authority
- JP
- Japan
- Prior art keywords
- composition
- triptolide
- sodium
- oil
- group
- 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
- 239000000203 mixture Substances 0.000 claims description 42
- DFBIRQPKNDILPW-CIVMWXNOSA-N Triptolide Chemical compound O=C1OCC([C@@H]2C3)=C1CC[C@]2(C)[C@]12O[C@H]1[C@@H]1O[C@]1(C(C)C)[C@@H](O)[C@]21[C@H]3O1 DFBIRQPKNDILPW-CIVMWXNOSA-N 0.000 claims description 40
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 20
- 239000000839 emulsion Substances 0.000 claims description 16
- 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 16
- 150000002632 lipids Chemical class 0.000 claims description 12
- 235000011187 glycerol Nutrition 0.000 claims description 10
- 150000003904 phospholipids Chemical class 0.000 claims description 10
- NRHMKIHPTBHXPF-TUJRSCDTSA-M sodium cholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 NRHMKIHPTBHXPF-TUJRSCDTSA-M 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 229940057917 medium chain triglycerides Drugs 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000001990 intravenous administration Methods 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- YRIMSXJXBHUHJT-UHFFFAOYSA-N 2,3-di(nonanoyloxy)propyl nonanoate Chemical compound CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC)COC(=O)CCCCCCCC YRIMSXJXBHUHJT-UHFFFAOYSA-N 0.000 claims description 2
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 claims description 2
- 235000010469 Glycine max Nutrition 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
- 206010062016 Immunosuppression Diseases 0.000 claims description 2
- 235000006679 Mentha X verticillata Nutrition 0.000 claims description 2
- 235000002899 Mentha suaveolens Nutrition 0.000 claims description 2
- 235000001636 Mentha x rotundifolia Nutrition 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- FVJZSBGHRPJMMA-IOLBBIBUSA-N PG(18:0/18:0) Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@@H](O)CO)OC(=O)CCCCCCCCCCCCCCCCC FVJZSBGHRPJMMA-IOLBBIBUSA-N 0.000 claims description 2
- 235000019483 Peanut oil Nutrition 0.000 claims description 2
- 230000006907 apoptotic process Effects 0.000 claims description 2
- 239000004359 castor oil Substances 0.000 claims description 2
- 235000019438 castor oil Nutrition 0.000 claims description 2
- 230000004663 cell proliferation Effects 0.000 claims description 2
- 239000003240 coconut oil Substances 0.000 claims description 2
- 235000019864 coconut oil Nutrition 0.000 claims description 2
- 235000005687 corn oil Nutrition 0.000 claims description 2
- 239000002285 corn oil Substances 0.000 claims description 2
- 235000012343 cottonseed oil Nutrition 0.000 claims description 2
- 239000002385 cottonseed oil Substances 0.000 claims description 2
- CITHEXJVPOWHKC-UHFFFAOYSA-N dimyristoyl phosphatidylcholine Chemical compound CCCCCCCCCCCCCC(=O)OCC(COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCC CITHEXJVPOWHKC-UHFFFAOYSA-N 0.000 claims description 2
- 229960005160 dimyristoylphosphatidylglycerol Drugs 0.000 claims description 2
- 229960004756 ethanol Drugs 0.000 claims description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 2
- 230000002519 immonomodulatory effect Effects 0.000 claims description 2
- 230000001506 immunosuppresive effect Effects 0.000 claims description 2
- 230000001939 inductive effect Effects 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 239000004006 olive oil Substances 0.000 claims description 2
- 235000008390 olive oil Nutrition 0.000 claims description 2
- 239000003346 palm kernel oil Substances 0.000 claims description 2
- 235000019865 palm kernel oil Nutrition 0.000 claims description 2
- 239000000312 peanut oil Substances 0.000 claims description 2
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 2
- 229940068886 polyethylene glycol 300 Drugs 0.000 claims description 2
- 229940068918 polyethylene glycol 400 Drugs 0.000 claims description 2
- 229960004063 propylene glycol Drugs 0.000 claims description 2
- 235000005713 safflower oil Nutrition 0.000 claims description 2
- 239000003813 safflower oil Substances 0.000 claims description 2
- 239000008159 sesame oil Substances 0.000 claims description 2
- 235000011803 sesame oil Nutrition 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- AAYACJGHNRIFCT-YRJJIGPTSA-M sodium glycochenodeoxycholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC([O-])=O)C)[C@@]2(C)CC1 AAYACJGHNRIFCT-YRJJIGPTSA-M 0.000 claims description 2
- OABYVIYXWMZFFJ-ZUHYDKSRSA-M sodium glycocholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 OABYVIYXWMZFFJ-ZUHYDKSRSA-M 0.000 claims description 2
- VMSNAUAEKXEYGP-YEUHZSMFSA-M sodium glycodeoxycholate Chemical compound [Na+].C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC([O-])=O)C)[C@@]2(C)[C@@H](O)C1 VMSNAUAEKXEYGP-YEUHZSMFSA-M 0.000 claims description 2
- JAJWGJBVLPIOOH-IZYKLYLVSA-M sodium taurocholate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 JAJWGJBVLPIOOH-IZYKLYLVSA-M 0.000 claims description 2
- 229940045946 sodium taurodeoxycholate Drugs 0.000 claims description 2
- YXHRQQJFKOHLAP-FVCKGWAHSA-M sodium;2-[[(4r)-4-[(3r,5r,8r,9s,10s,12s,13r,14s,17r)-3,12-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonate Chemical compound [Na+].C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS([O-])(=O)=O)C)[C@@]2(C)[C@@H](O)C1 YXHRQQJFKOHLAP-FVCKGWAHSA-M 0.000 claims description 2
- IYPNVUSIMGAJFC-HLEJRKHJSA-M sodium;2-[[(4r)-4-[(3r,5s,7r,8r,9s,10s,13r,14s,17r)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]ethanesulfonate Chemical compound [Na+].C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCCS([O-])(=O)=O)C)[C@@]2(C)CC1 IYPNVUSIMGAJFC-HLEJRKHJSA-M 0.000 claims description 2
- 239000003549 soybean oil Substances 0.000 claims description 2
- 235000012424 soybean oil Nutrition 0.000 claims description 2
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 claims description 2
- MAYCICSNZYXLHB-UHFFFAOYSA-N tricaproin Chemical compound CCCCCC(=O)OCC(OC(=O)CCCCC)COC(=O)CCCCC MAYCICSNZYXLHB-UHFFFAOYSA-N 0.000 claims description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 2
- PJHKBYALYHRYSK-UHFFFAOYSA-N triheptanoin Chemical compound CCCCCCC(=O)OCC(OC(=O)CCCCCC)COC(=O)CCCCCC PJHKBYALYHRYSK-UHFFFAOYSA-N 0.000 claims description 2
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 description 3
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361794926P | 2013-03-15 | 2013-03-15 | |
| US61/794,926 | 2013-03-15 | ||
| PCT/US2014/030041 WO2014145303A1 (en) | 2013-03-15 | 2014-03-15 | Intravenous emulsions of triptolide as immunomodulators and anticancer agents i |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016515530A JP2016515530A (ja) | 2016-05-30 |
| JP2016515530A5 true JP2016515530A5 (https=) | 2017-04-13 |
Family
ID=51537944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016503315A Pending JP2016515530A (ja) | 2013-03-15 | 2014-03-15 | 免疫調節薬および抗がん剤としてのトリプトリドの静脈内乳剤 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20160038454A1 (https=) |
| EP (1) | EP2968140A4 (https=) |
| JP (1) | JP2016515530A (https=) |
| CN (1) | CN105263475A (https=) |
| HK (1) | HK1219228A1 (https=) |
| TW (1) | TWI597071B (https=) |
| WO (1) | WO2014145303A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6931228B2 (ja) * | 2015-09-11 | 2021-09-01 | ワイズ・エー・シー株式会社 | 抗ｃｄ２６抗体と他の抗癌剤とを組み合わせた癌治療用組成物 |
| US10342797B2 (en) | 2016-03-13 | 2019-07-09 | LivePet, LLC | Solubility of therapeutic agents |
| CN107663225A (zh) * | 2016-07-29 | 2018-02-06 | 欣凯医药化工中间体（上海）有限公司 | 一种氟代雷公藤内酯醇内酯环衍生物 |
| CN108530511B (zh) * | 2017-03-02 | 2021-06-22 | 欣凯医药化工中间体（上海）有限公司 | 一种c19-酰基化雷公藤甲素衍生物 |
| CN106946975B (zh) * | 2017-03-16 | 2020-08-14 | 上海天氏利医药科技有限公司 | 一种雷公藤甲素衍生物及其制备方法与制剂 |
| CN106994129A (zh) * | 2017-05-15 | 2017-08-01 | 王晓辉 | 雷公藤甲素及其衍生物在制备治疗和/或预防肺损伤疾病的药物中的应用 |
| WO2018222351A1 (en) * | 2017-05-27 | 2018-12-06 | Pharmagenesis, Inc. | Triptolide lactone derivatives as immunomodulators and anticancer agents |
| EP3761961A4 (en) * | 2018-03-07 | 2022-01-05 | Andrew Xian Chen | Aqueous formulations for insoluble medicinal products |
| CN109771430A (zh) * | 2019-03-15 | 2019-05-21 | 大连大学 | 甘氨胆酸在制备抗肿瘤药物中的应用 |
| CN111494319A (zh) * | 2020-06-15 | 2020-08-07 | 沈阳药科大学 | 雷公藤甲素复方组合物及其制备方法与应用 |
| CN115466269A (zh) * | 2021-06-11 | 2022-12-13 | 复旦大学 | 一种胆碱碳酸酯类前药及其制备方法和应用 |
| CN114569554A (zh) * | 2022-03-01 | 2022-06-03 | 福建省医学科学研究院 | 一种肿瘤靶向性雷公藤内酯醇乳液及其制备方法 |
| CN114831962A (zh) * | 2022-04-29 | 2022-08-02 | 福建省医学科学研究院 | 一种雷公藤内酯醇固体脂质纳米粒及其滴丸的制备方法 |
| WO2023221961A1 (zh) * | 2022-05-20 | 2023-11-23 | 上海维洱生物医药科技有限公司 | 一种雷公藤甲素木蜡酸酯及其脂质体与制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU3631795A (en) * | 1994-09-15 | 1996-03-29 | Pharmagenesis, Inc. | Composition and method for immunotherapy |
| WO2004058246A1 (en) * | 2002-12-17 | 2004-07-15 | Pharmagenesis, Inc. | Triptolide derivatives as immunomodulator and anticancer agents |
| WO2005084365A2 (en) * | 2004-03-02 | 2005-09-15 | Pharmagenesis, Inc. | Triptolide lactone ring derivatives as immunomodulators and anticancer agents |
| UA89545C2 (uk) * | 2005-08-29 | 2010-02-10 | Сепсикюр Л.Л.К. | Спосіб лікування чи попередження станів, викликаних грампозитивними бактеріями |
| CN101485629B (zh) * | 2008-01-16 | 2013-01-23 | 沈阳药科大学 | 一种给药系统及其制备方法 |
| TW201138782A (en) * | 2010-04-26 | 2011-11-16 | Besins Healthcare Lu Sarl | Low-oil pharmaceutical emulsion compositions comprising progestogen |
| CN102793674B (zh) * | 2011-05-26 | 2014-11-26 | 澳门科技大学 | 一种雷公藤甲素固体脂质纳米颗粒及其制备方法和应用 |
| CN102552137B (zh) * | 2012-02-22 | 2013-04-10 | 福建医科大学 | 雷公藤内酯醇脂肪乳注射剂及其制备方法 |
-
2014
- 2014-03-15 EP EP14765049.3A patent/EP2968140A4/en not_active Withdrawn
- 2014-03-15 US US14/776,606 patent/US20160038454A1/en not_active Abandoned
- 2014-03-15 CN CN201480015321.7A patent/CN105263475A/zh active Pending
- 2014-03-15 JP JP2016503315A patent/JP2016515530A/ja active Pending
- 2014-03-15 WO PCT/US2014/030041 patent/WO2014145303A1/en not_active Ceased
- 2014-03-15 HK HK16107282.4A patent/HK1219228A1/zh unknown
- 2014-03-17 TW TW103109891A patent/TWI597071B/zh active
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