JP2013511540A5 - - Google Patents
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- Publication number
- JP2013511540A5 JP2013511540A5 JP2012540065A JP2012540065A JP2013511540A5 JP 2013511540 A5 JP2013511540 A5 JP 2013511540A5 JP 2012540065 A JP2012540065 A JP 2012540065A JP 2012540065 A JP2012540065 A JP 2012540065A JP 2013511540 A5 JP2013511540 A5 JP 2013511540A5
- Authority
- JP
- Japan
- Prior art keywords
- irinotecan
- glycine
- hydrogen halide
- salt
- composition
- 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
- 229960004768 irinotecan Drugs 0.000 claims description 72
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 65
- 239000012433 hydrogen halide Substances 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 51
- 150000003839 salts Chemical group 0.000 claims description 47
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 23
- 239000004698 Polyethylene Substances 0.000 claims description 20
- UWKQSNNFCGGAFS-XIFFEERXSA-N irinotecan Chemical compound C1=C2C(CC)=C3CN(C(C4=C([C@@](C(=O)OC4)(O)CC)C=4)=O)C=4C3=NC2=CC=C1OC(=O)N(CC1)CCC1N1CCCCC1 UWKQSNNFCGGAFS-XIFFEERXSA-N 0.000 claims description 20
- 229920000573 polyethylene Polymers 0.000 claims description 20
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 206010028980 Neoplasm Diseases 0.000 claims description 14
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 12
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 10
- 238000001556 precipitation Methods 0.000 claims description 10
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004471 Glycine Substances 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 229920002214 alkoxylated polymer Polymers 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000004820 halides Chemical class 0.000 claims description 4
- 238000004255 ion exchange chromatography Methods 0.000 claims description 4
- 239000002861 polymer material Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 206010008342 Cervix carcinoma Diseases 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical group [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims description 2
- 201000010881 cervical cancer Diseases 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 239000008121 dextrose Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 150000004673 fluoride salts Chemical group 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- 238000001802 infusion Methods 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 238000001990 intravenous administration Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 claims description 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 230000004614 tumor growth Effects 0.000 claims description 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims description 2
- 241000124008 Mammalia Species 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US26246309P | 2009-11-18 | 2009-11-18 | |
| US61/262,463 | 2009-11-18 | ||
| US29007209P | 2009-12-24 | 2009-12-24 | |
| US61/290,072 | 2009-12-24 | ||
| PCT/US2010/057292 WO2011063158A1 (en) | 2009-11-18 | 2010-11-18 | Salt form of a multi-arm polymer-drug conjugate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013511540A JP2013511540A (ja) | 2013-04-04 |
| JP2013511540A5 true JP2013511540A5 (enExample) | 2013-11-21 |
| JP5901073B2 JP5901073B2 (ja) | 2016-04-06 |
Family
ID=43639124
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012540064A Active JP5951496B2 (ja) | 2009-11-18 | 2010-11-18 | ポリマー−薬物コンジュゲートの酸性塩形態及びアルコキシル化方法 |
| JP2012540065A Active JP5901073B2 (ja) | 2009-11-18 | 2010-11-18 | マルチアームポリマー−薬物コンジュゲートの塩形態 |
| JP2015199074A Pending JP2016006127A (ja) | 2009-11-18 | 2015-10-07 | ポリマー−薬物コンジュゲートの酸性塩形態及びアルコキシル化方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012540064A Active JP5951496B2 (ja) | 2009-11-18 | 2010-11-18 | ポリマー−薬物コンジュゲートの酸性塩形態及びアルコキシル化方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015199074A Pending JP2016006127A (ja) | 2009-11-18 | 2015-10-07 | ポリマー−薬物コンジュゲートの酸性塩形態及びアルコキシル化方法 |
Country Status (24)
| Country | Link |
|---|---|
| US (5) | US9226969B2 (enExample) |
| EP (3) | EP3498754A1 (enExample) |
| JP (3) | JP5951496B2 (enExample) |
| KR (2) | KR101790804B1 (enExample) |
| CN (2) | CN102711837B (enExample) |
| AU (1) | AU2010321882B2 (enExample) |
| BR (2) | BR112012011947B8 (enExample) |
| CA (3) | CA2780645C (enExample) |
| CY (1) | CY1121700T1 (enExample) |
| DK (1) | DK2501413T3 (enExample) |
| EA (2) | EA023503B1 (enExample) |
| ES (2) | ES2623677T3 (enExample) |
| HR (1) | HRP20191138T1 (enExample) |
| HU (1) | HUE043689T2 (enExample) |
| IL (2) | IL219866A (enExample) |
| LT (1) | LT2501413T (enExample) |
| ME (1) | ME03396B (enExample) |
| MX (2) | MX337393B (enExample) |
| PL (1) | PL2501413T3 (enExample) |
| PT (1) | PT2501413T (enExample) |
| RS (1) | RS58901B1 (enExample) |
| SI (1) | SI2501413T1 (enExample) |
| SM (1) | SMT201900294T1 (enExample) |
| WO (2) | WO2011063158A1 (enExample) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8852638B2 (en) | 2005-09-30 | 2014-10-07 | Durect Corporation | Sustained release small molecule drug formulation |
| EP2152315B1 (en) | 2007-05-25 | 2016-01-06 | Indivior UK Limited | Sustained delivery formulations of risperidone compounds |
| CA2780645C (en) | 2009-11-18 | 2018-01-16 | Nektar Therapeutics | Salt form of a multi-arm polymer-drug conjugate |
| GB2513060B (en) | 2010-06-08 | 2015-01-07 | Rb Pharmaceuticals Ltd | Microparticle buprenorphine suspension |
| US9272044B2 (en) | 2010-06-08 | 2016-03-01 | Indivior Uk Limited | Injectable flowable composition buprenorphine |
| JP6138140B2 (ja) * | 2011-10-25 | 2017-05-31 | ネクター セラピューティクス | 癌患者の治療 |
| WO2013162387A1 (en) * | 2012-04-26 | 2013-10-31 | Amylex Pharmaceuticals, Inc | Novel composition for extracorporeal reduction of beta-amyloids and process for producing thereof |
| JP6300460B2 (ja) * | 2012-07-20 | 2018-03-28 | キヤノン株式会社 | 化合物、および前記化合物を有する光音響イメージング用造影剤 |
| WO2014036566A1 (en) * | 2012-08-31 | 2014-03-06 | Virginia Commonwealth University | Clickable polyoxetane carrier for drug delivery |
| CN104813167B (zh) | 2012-11-28 | 2019-04-09 | 尼克塔治疗公司 | 用于评估和预测用一种长效拓扑异构酶i抑制剂进行乳腺癌治疗的疗效的方法 |
| US9493766B2 (en) * | 2013-02-04 | 2016-11-15 | Corning Incorporated | PCR reaction cleanup buffers |
| CN105492011A (zh) | 2013-04-08 | 2016-04-13 | 丹尼斯·M·布朗 | 不理想给药化学化合物的治疗增效 |
| WO2014194289A1 (en) | 2013-05-31 | 2014-12-04 | Nektar Therapeutics | Method for predicting and evaluating responsiveness to cancer treatment with dna-damaging chemotherapeutic agents |
| CN104225611B (zh) * | 2013-06-18 | 2017-06-30 | 天津键凯科技有限公司 | 达沙替尼与非线性构型聚乙二醇的结合物 |
| CA3191031A1 (en) | 2013-09-27 | 2015-04-02 | Massachusetts Institute Of Technology | Carrier-free biologically-active protein nanostructures |
| CN106061483B (zh) * | 2013-10-04 | 2021-01-08 | 普洛林克斯有限责任公司 | Sn-38的缓释结合物 |
| JP5721806B2 (ja) * | 2013-10-04 | 2015-05-20 | Ｄｅｌｔａ−Ｆｌｙ Ｐｈａｒｍａ株式会社 | 副作用のない抗癌剤 |
| AU2015206667B2 (en) | 2014-01-14 | 2020-05-14 | Nektar Therapeutics | Combination-based treatment method |
| GB201404139D0 (en) | 2014-03-10 | 2014-04-23 | Rb Pharmaceuticals Ltd | Sustained release buprenorphine solution formulations |
| EP3228650B1 (en) * | 2014-12-04 | 2022-03-09 | Delta-Fly Pharma, Inc. | Novel peg derivative |
| EP3253777B9 (en) * | 2015-02-04 | 2021-11-17 | United Arab Emirates University | Rvg derived peptides |
| AU2016305087B2 (en) | 2015-08-12 | 2022-01-20 | Massachusetts Institute Of Technology | Cell surface coupling of nanoparticles |
| CN107019803B (zh) * | 2016-01-29 | 2020-09-15 | 北京键凯科技股份有限公司 | 具有低成瘾作用的聚乙二醇化阿片样物质 |
| CN107375288B (zh) | 2016-05-16 | 2019-08-23 | 博瑞生物医药（苏州）股份有限公司 | 多臂的聚合靶向抗癌偶联物 |
| CN107469089B (zh) * | 2016-06-07 | 2022-01-07 | 北京键凯科技股份有限公司 | 一种peg连接子及配基药物偶联物 |
| CN109715196A (zh) | 2016-06-13 | 2019-05-03 | 转矩医疗股份有限公司 | 用于促进免疫细胞功能的组合物和方法 |
| AU2018207283C1 (en) | 2017-01-10 | 2024-05-02 | Nektar Therapeutics | Multi-arm polymer conjugates of TLR agonist compounds and related immunotherapeutic treatment methods |
| WO2018143122A1 (ja) * | 2017-02-02 | 2018-08-09 | アルプス電気株式会社 | 平衡式電流センサ |
| KR102279429B1 (ko) | 2017-04-21 | 2021-07-20 | 브라이트제네 바이오-메디컬 테크놀로지 코., 엘티디. | 멀티 암 표적 항암 콘쥬게이트 |
| CN108727584B (zh) * | 2017-04-21 | 2021-01-05 | 博瑞生物医药（苏州）股份有限公司 | 抗癌偶联物 |
| WO2019046452A1 (en) * | 2017-09-01 | 2019-03-07 | Arizona Board Of Regents On Behalf Of Arizona State University | THIXOTROPIC BIOCOMPATIBLE GEL FOR OBSERVATION OF LIVING CELLS IN COMPUTER-ASSISTED TOMOGRAPHY ON CELLS |
| CA3074826A1 (en) | 2017-09-05 | 2019-03-14 | Torque Therapeutics, Inc. | Therapeutic protein compositions and methods of making and using the same |
| WO2019096096A1 (zh) * | 2017-11-14 | 2019-05-23 | 博瑞生物医药（苏州）股份有限公司 | 多臂靶向偶联物 |
| CN107854693B (zh) * | 2017-11-14 | 2020-07-14 | 高瑞耀业(北京)科技有限公司 | 整合素受体靶向的抗癌偶联物 |
| CN109776787B (zh) * | 2017-11-14 | 2021-08-03 | 博瑞生物医药（苏州）股份有限公司 | 多臂靶向偶联物 |
| CN111526891B (zh) * | 2017-12-27 | 2023-10-20 | 三洋化成工业株式会社 | 药品原料药用原料或药品用添加物和使用了它们的药品原料药或药品 |
| JP2021510702A (ja) | 2018-01-12 | 2021-04-30 | プロリンクス エルエルシー | 相乗的がん治療 |
| CN112367985A (zh) | 2018-01-31 | 2021-02-12 | 明尼苏达大学董事会 | 用于治疗肺水肿或肺炎的组合物和方法 |
| CN110256533B (zh) * | 2018-03-12 | 2022-05-10 | 博瑞生物医药（苏州）股份有限公司 | 一种高纯度的多臂抗癌偶联物的提取方法 |
| CN110577552A (zh) * | 2018-06-08 | 2019-12-17 | 遵义医学院 | 喜树碱-甘氨酸-5,6-双脱氢去甲斑蝥素结合物及其应用 |
| EP3852793B1 (en) | 2018-09-17 | 2025-11-19 | The Children's Hospital Of Philadelphia | Macromolecular prodrug peg-[sn22]4 |
| CN111603567B (zh) | 2019-02-22 | 2024-12-27 | 赣江新区博瑞创新医药有限公司 | Cd44靶向多臂偶联物 |
| US20220305025A1 (en) * | 2019-08-15 | 2022-09-29 | The Research Foundation For The State University Of New York | Phosphatidylserine binding molecules block immune suppression of tumor associated exosomes |
| MX2022011821A (es) | 2020-03-27 | 2022-10-10 | Univ Minnesota | Composiciones y metodos para tratar edema pulmonar o inflamacion pulmonar. |
| CN114705801B (zh) * | 2022-01-24 | 2024-02-27 | 中国食品药品检定研究院(国家药品监督管理局医疗器械标准管理中心、中国药品检验总所) | 一种利福霉素类药物中亚硝酸根离子的测定方法 |
| WO2025053315A1 (ko) * | 2023-09-08 | 2025-03-13 | 파로스젠 주식회사 | 항암제 프로드러그 컨쥬게이트의 제조에서 팔라듐의 회수 및 제거 방법 |
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| CA2780645C (en) | 2009-11-18 | 2018-01-16 | Nektar Therapeutics | Salt form of a multi-arm polymer-drug conjugate |
-
2010
- 2010-11-18 CA CA2780645A patent/CA2780645C/en active Active
- 2010-11-18 EA EA201200751A patent/EA023503B1/ru unknown
- 2010-11-18 CA CA3063465A patent/CA3063465C/en active Active
- 2010-11-18 ES ES10781794.2T patent/ES2623677T3/es active Active
- 2010-11-18 PT PT10782159T patent/PT2501413T/pt unknown
- 2010-11-18 EP EP19152138.4A patent/EP3498754A1/en active Pending
- 2010-11-18 CN CN201080061613.6A patent/CN102711837B/zh active Active
- 2010-11-18 HU HUE10782159A patent/HUE043689T2/hu unknown
- 2010-11-18 DK DK10782159.7T patent/DK2501413T3/da active
- 2010-11-18 RS RS20190781A patent/RS58901B1/sr unknown
- 2010-11-18 MX MX2012005795A patent/MX337393B/es active IP Right Grant
- 2010-11-18 ES ES10782159T patent/ES2723026T3/es active Active
- 2010-11-18 PL PL10782159T patent/PL2501413T3/pl unknown
- 2010-11-18 JP JP2012540064A patent/JP5951496B2/ja active Active
- 2010-11-18 WO PCT/US2010/057292 patent/WO2011063158A1/en not_active Ceased
- 2010-11-18 HR HRP20191138TT patent/HRP20191138T1/hr unknown
- 2010-11-18 EP EP10782159.7A patent/EP2501413B1/en active Active
- 2010-11-18 EP EP10781794.2A patent/EP2501412B1/en active Active
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