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 (https=) | 2013-11-21 |
| JP5901073B2 JP5901073B2 (ja) | 2016-04-06 |
Family
ID=43639124
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| 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 |
| 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 |
| 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 After (2)
| 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 |
| 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) | US20130143909A1 (https=) |
| EP (3) | EP2501413B1 (https=) |
| JP (3) | JP5901073B2 (https=) |
| KR (2) | KR101779229B1 (https=) |
| CN (2) | CN102711837B (https=) |
| AU (1) | AU2010321882B2 (https=) |
| BR (2) | BR112012011947B8 (https=) |
| CA (3) | CA2780645C (https=) |
| CY (1) | CY1121700T1 (https=) |
| DK (1) | DK2501413T3 (https=) |
| EA (2) | EA023503B1 (https=) |
| ES (2) | ES2723026T3 (https=) |
| HR (1) | HRP20191138T1 (https=) |
| HU (1) | HUE043689T2 (https=) |
| IL (2) | IL219865A (https=) |
| LT (1) | LT2501413T (https=) |
| ME (1) | ME03396B (https=) |
| MX (2) | MX337393B (https=) |
| PL (1) | PL2501413T3 (https=) |
| PT (1) | PT2501413T (https=) |
| RS (1) | RS58901B1 (https=) |
| SI (1) | SI2501413T1 (https=) |
| SM (1) | SMT201900294T1 (https=) |
| WO (2) | WO2011063158A1 (https=) |
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 |
| ES2562878T3 (es) | 2007-05-25 | 2016-03-08 | Indivior Uk Limited | Formulaciones de liberación sostenida de compuestos de risperidona |
| PT2501413T (pt) | 2009-11-18 | 2019-07-10 | Nektar Therapeutics | Formas de sal de ácido de conjugados de polímero-fármaco |
| US9272044B2 (en) | 2010-06-08 | 2016-03-01 | Indivior Uk Limited | Injectable flowable composition buprenorphine |
| GB2513060B (en) | 2010-06-08 | 2015-01-07 | Rb Pharmaceuticals Ltd | Microparticle buprenorphine suspension |
| EP2771034B1 (en) * | 2011-10-25 | 2018-08-08 | Nektar Therapeutics | Topoisomerase-i and-ii inhibitors for use in the treatment of patients suffering from cancer |
| AU2013253098A1 (en) * | 2012-04-26 | 2014-11-13 | 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 |
| US9421276B2 (en) * | 2012-08-31 | 2016-08-23 | Virginia Commonwealth University | Clickable polyoxetane carrier for drug delivery |
| WO2014085571A1 (en) | 2012-11-28 | 2014-06-05 | Nektar Therapeutics | Method for assessing and predicting efficacy of breast cancer treatment with a long-acting topoisomerase i inhibitor |
| US9493766B2 (en) * | 2013-02-04 | 2016-11-15 | Corning Incorporated | PCR reaction cleanup buffers |
| KR20160061911A (ko) | 2013-04-08 | 2016-06-01 | 데니스 엠. 브라운 | 최적하 투여된 화학 화합물의 치료 효과 |
| 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 |
| JP5721806B2 (ja) * | 2013-10-04 | 2015-05-20 | Ｄｅｌｔａ−Ｆｌｙ Ｐｈａｒｍａ株式会社 | 副作用のない抗癌剤 |
| MX371201B (es) * | 2013-10-04 | 2020-01-22 | Prolynx Llc | Conjugados de liberación lenta de sn-38. |
| MX386070B (es) | 2014-01-14 | 2025-03-18 | Nektar Therapeutics | Metodo de tratamiento basado en combinacion. |
| 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 |
| WO2016124976A1 (en) * | 2015-02-04 | 2016-08-11 | United Arab Emirates University | Rvg derived peptides |
| WO2017027843A1 (en) | 2015-08-12 | 2017-02-16 | 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 |
| KR102619747B1 (ko) | 2017-01-10 | 2023-12-29 | 넥타르 테라퓨틱스 | Tlr 효현제 화합물의 다중-아암 중합체 컨쥬게이트 및 관련 면역 요법적 치료 방법 |
| CN110235003B (zh) * | 2017-02-02 | 2022-04-01 | 阿尔卑斯阿尔派株式会社 | 平衡式电流传感器 |
| 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 |
| KR102279429B1 (ko) | 2017-04-21 | 2021-07-20 | 브라이트제네 바이오-메디컬 테크놀로지 코., 엘티디. | 멀티 암 표적 항암 콘쥬게이트 |
| 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 |
| WO2019131515A1 (ja) | 2017-12-27 | 2019-07-04 | 三洋化成工業株式会社 | 医薬品原薬用原料又は医薬品用添加物及びこれらを用いた医薬品原薬又は医薬品 |
| MX2020007442A (es) * | 2018-01-12 | 2020-09-14 | Prolynx Llc | Protocolo para minimizar la toxicidad de dosificaciones de combinacion y agente formador de imagen para verificacion. |
| MX2020007971A (es) | 2018-01-31 | 2020-09-09 | Univ Minnesota | Composiciones y metodos para tratar edema pulmonar o inflamacion pulmonar. |
| 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 |
| CA3112778A1 (en) | 2018-09-17 | 2020-03-26 | The Children's Hospital Of Philadelphia | Polymer-based macromolecular prodrugs |
| 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 |
| JP2022545402A (ja) * | 2019-08-15 | 2022-10-27 | ザ リサーチ ファウンデイション フォー ザ ステイト ユニバーシティー オブ ニューヨーク | 腫瘍関連エキソソームの免疫抑制をブロックするホスファチジルセリン結合分子 |
| EP4126104A4 (en) | 2020-03-27 | 2024-04-17 | Regents of the University of Minnesota | COMPOSITIONS AND METHODS FOR TREATING PULMONARY EDEMA OR PNEUMATIC INFLAMMATION |
| 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 |
| CN121843719A (zh) * | 2023-09-08 | 2026-04-10 | 法罗斯根有限公司 | 在制备抗癌剂前药偶联物中回收和去除钯的方法 |
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| PT2501413T (pt) | 2009-11-18 | 2019-07-10 | Nektar Therapeutics | Formas de sal de ácido de conjugados de polímero-fármaco |
-
2010
- 2010-11-18 PT PT10782159T patent/PT2501413T/pt unknown
- 2010-11-18 ES ES10782159T patent/ES2723026T3/es active Active
- 2010-11-18 PL PL10782159T patent/PL2501413T3/pl unknown
- 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 WO PCT/US2010/057289 patent/WO2011063156A2/en not_active Ceased
- 2010-11-18 BR BR112012011947A patent/BR112012011947B8/pt active IP Right Grant
- 2010-11-18 SI SI201031891T patent/SI2501413T1/sl unknown
- 2010-11-18 CA CA2780645A patent/CA2780645C/en active Active
- 2010-11-18 JP JP2012540065A patent/JP5901073B2/ja active Active
- 2010-11-18 EP EP10782159.7A patent/EP2501413B1/en active Active
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