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 |
|---|---|---|---|
| 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) | US9226969B2 (enExample) |
| EP (3) | EP2501413B1 (enExample) |
| JP (3) | JP5901073B2 (enExample) |
| KR (2) | KR101779229B1 (enExample) |
| CN (2) | CN102711836B (enExample) |
| AU (1) | AU2010321882B2 (enExample) |
| BR (2) | BR112012011943A2 (enExample) |
| CA (3) | CA3063465C (enExample) |
| CY (1) | CY1121700T1 (enExample) |
| DK (1) | DK2501413T3 (enExample) |
| EA (2) | EA024533B1 (enExample) |
| ES (2) | ES2723026T3 (enExample) |
| HR (1) | HRP20191138T1 (enExample) |
| HU (1) | HUE043689T2 (enExample) |
| IL (2) | IL219866A (enExample) |
| LT (1) | LT2501413T (enExample) |
| ME (1) | ME03396B (enExample) |
| MX (2) | MX338134B (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 (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8852638B2 (en) | 2005-09-30 | 2014-10-07 | Durect Corporation | Sustained release small molecule drug formulation |
| CN101801415B (zh) | 2007-05-25 | 2015-09-23 | Rb医药品有限公司 | 利培酮化合物的持续递送制剂 |
| ME03396B (me) | 2009-11-18 | 2020-01-20 | Nektar Therapeutics | Oblici kisele soli konjugata polimer-lek |
| GB2481017B (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 |
| 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 |
| US20150087591A1 (en) * | 2012-04-26 | 2015-03-26 | 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 |
| MX366911B (es) | 2012-11-28 | 2019-07-30 | Nektar Therapeutics | Método para evaluar y predecir la eficacia del tratamiento del cáncer de mama con un inhibidor de topoisomerasa i de acción prolongada. |
| US9493766B2 (en) * | 2013-02-04 | 2016-11-15 | Corning Incorporated | PCR reaction cleanup buffers |
| US11491154B2 (en) | 2013-04-08 | 2022-11-08 | Dennis M. Brown | Therapeutic benefit of suboptimally administered chemical compounds |
| EP3004888A1 (en) | 2013-05-31 | 2016-04-13 | 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 |
| EP3049114B1 (en) * | 2013-09-27 | 2021-11-10 | Massachusetts Institute of Technology | Carrier-free biologically-active protein nanostructures |
| ES2759905T3 (es) * | 2013-10-04 | 2020-05-12 | Prolynx Llc | Conjugados de liberación lenta de SN-38 |
| JP5721806B2 (ja) * | 2013-10-04 | 2015-05-20 | Ｄｅｌｔａ−Ｆｌｙ Ｐｈａｒｍａ株式会社 | 副作用のない抗癌剤 |
| CA2934552C (en) | 2014-01-14 | 2021-03-30 | Nektar Therapeutics | Combination-based treatment method |
| GB201404139D0 (en) | 2014-03-10 | 2014-04-23 | Rb Pharmaceuticals Ltd | Sustained release buprenorphine solution formulations |
| ES2910659T3 (es) * | 2014-12-04 | 2022-05-13 | Delta Fly Pharma Inc | Nuevo derivado de PEG |
| WO2016124976A1 (en) * | 2015-02-04 | 2016-08-11 | United Arab Emirates University | Rvg derived peptides |
| US11034752B2 (en) | 2015-08-12 | 2021-06-15 | 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 |
| CA3029813A1 (en) | 2016-06-13 | 2017-12-21 | Torque Therapeutics, Inc. | Methods and compositions for promoting immune cell function |
| 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 |
| JP6947909B2 (ja) * | 2017-04-21 | 2021-10-13 | 博瑞生物医薬（蘇州）股▲分▼有限公司Ｂｒｉｇｈｔｇｅｎｅ Ｂｉｏ−Ｍｅｄｉｃａｌ Ｔｅｃｈｎｏｌｏｇｙ Ｃｏ．， Ｌｔｄ． | マルチアーム標的抗がんコンジュゲート |
| 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 |
| US12329382B2 (en) | 2017-09-01 | 2025-06-17 | Arizona Board Of Regents On Behalf Of Arizona State University | Thixotropic biocompatible gel for live cell observation in cell computed tomography |
| WO2019050978A1 (en) | 2017-09-05 | 2019-03-14 | Torque Therapeutics, Inc. | THERAPEUTIC PROTEIN COMPOSITIONS AND METHODS OF PREPARATION AND USE THEREOF |
| 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 |
| 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 |
| 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 |
| US11299587B2 (en) | 2017-12-27 | 2022-04-12 | Sanyo Chemical Industries, Ltd. | Starting material, for bulk drug or additives for drug, and bulk drug or drug using same |
| WO2019140266A1 (en) * | 2018-01-12 | 2019-07-18 | Prolynx Llc | Protocol for minimizing toxicity of combination dosages and imaging agent for verification |
| 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 |
| JP7546552B2 (ja) * | 2018-09-17 | 2024-09-06 | ザ・チルドレンズ・ホスピタル・オブ・フィラデルフィア | ポリマーベースの高分子プロドラッグ |
| 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 |
| KR20220099946A (ko) * | 2019-08-15 | 2022-07-14 | 더 리서치 파운데이션 포 더 스테이트 유니버시티 오브 뉴욕 | 종양 관련 엑소좀의 면역 억제를 차단하는 포스파티딜세린 결합 분자 |
| 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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| ME03396B (me) | 2009-11-18 | 2020-01-20 | Nektar Therapeutics | Oblici kisele soli konjugata polimer-lek |
-
2010
- 2010-11-18 ME MEP-2019-185A patent/ME03396B/me unknown
- 2010-11-18 ES ES10782159T patent/ES2723026T3/es active Active
- 2010-11-18 EA EA201290342A patent/EA024533B1/ru unknown
- 2010-11-18 CN CN201080061609.XA patent/CN102711836B/zh active Active
- 2010-11-18 US US13/510,587 patent/US9226969B2/en active Active
- 2010-11-18 EP EP10782159.7A patent/EP2501413B1/en active Active
- 2010-11-18 WO PCT/US2010/057292 patent/WO2011063158A1/en not_active Ceased
- 2010-11-18 EA EA201200751A patent/EA023503B1/ru unknown
- 2010-11-18 MX MX2012005794A patent/MX338134B/es active IP Right Grant
- 2010-11-18 HU HUE10782159A patent/HUE043689T2/hu unknown
- 2010-11-18 MX MX2012005795A patent/MX337393B/es active IP Right Grant
- 2010-11-18 DK DK10782159.7T patent/DK2501413T3/da active
- 2010-11-18 CA CA3063465A patent/CA3063465C/en active Active
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