JP2018505128A5 - - Google Patents
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- Publication number
- JP2018505128A5 JP2018505128A5 JP2017525940A JP2017525940A JP2018505128A5 JP 2018505128 A5 JP2018505128 A5 JP 2018505128A5 JP 2017525940 A JP2017525940 A JP 2017525940A JP 2017525940 A JP2017525940 A JP 2017525940A JP 2018505128 A5 JP2018505128 A5 JP 2018505128A5
- Authority
- JP
- Japan
- Prior art keywords
- buffer
- antibody
- process according
- solution
- piperazine
- 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.)
- Ceased
Links
- 238000000034 method Methods 0.000 claims description 93
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 239000011230 binding agent Substances 0.000 claims description 22
- 239000000872 buffer Substances 0.000 claims description 19
- 239000000243 solution Substances 0.000 claims description 19
- 230000001588 bifunctional effect Effects 0.000 claims description 18
- 239000003431 cross linking reagent Substances 0.000 claims description 18
- 239000007853 buffer solution Substances 0.000 claims description 17
- 231100000599 cytotoxic agent Toxicity 0.000 claims description 14
- 229940127089 cytotoxic agent Drugs 0.000 claims description 14
- 239000002254 cytotoxic agent Substances 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- OWXMKDGYPWMGEB-UHFFFAOYSA-N HEPPS Chemical compound OCCN1CCN(CCCS(O)(=O)=O)CC1 OWXMKDGYPWMGEB-UHFFFAOYSA-N 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 12
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 10
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 claims description 8
- LVQFQZZGTZFUNF-UHFFFAOYSA-N 2-hydroxy-3-[4-(2-hydroxy-3-sulfonatopropyl)piperazine-1,4-diium-1-yl]propane-1-sulfonate Chemical compound OS(=O)(=O)CC(O)CN1CCN(CC(O)CS(O)(=O)=O)CC1 LVQFQZZGTZFUNF-UHFFFAOYSA-N 0.000 claims description 7
- JOCBASBOOFNAJA-UHFFFAOYSA-N N-tris(hydroxymethyl)methyl-2-aminoethanesulfonic acid Chemical compound OCC(CO)(CO)NCCS(O)(=O)=O JOCBASBOOFNAJA-UHFFFAOYSA-N 0.000 claims description 7
- 239000011780 sodium chloride Substances 0.000 claims description 5
- SXGZJKUKBWWHRA-UHFFFAOYSA-N 2-(N-morpholiniumyl)ethanesulfonate Chemical compound [O-]S(=O)(=O)CC[NH+]1CCOCC1 SXGZJKUKBWWHRA-UHFFFAOYSA-N 0.000 claims description 4
- 239000007995 HEPES buffer Substances 0.000 claims description 4
- GIZQLVPDAOBAFN-UHFFFAOYSA-N HEPPSO Chemical group OCCN1CCN(CC(O)CS(O)(=O)=O)CC1 GIZQLVPDAOBAFN-UHFFFAOYSA-N 0.000 claims description 4
- 239000008351 acetate buffer Substances 0.000 claims description 4
- 239000007979 citrate buffer Substances 0.000 claims description 4
- 231100000433 cytotoxic Toxicity 0.000 claims description 4
- 230000001472 cytotoxic effect Effects 0.000 claims description 4
- 239000008363 phosphate buffer Substances 0.000 claims description 4
- YCLWMUYXEGEIGD-UHFFFAOYSA-M sodium;2-hydroxy-3-[4-(2-hydroxyethyl)piperazin-1-yl]propane-1-sulfonate Chemical compound [Na+].OCCN1CCN(CC(O)CS([O-])(=O)=O)CC1 YCLWMUYXEGEIGD-UHFFFAOYSA-M 0.000 claims description 4
- 239000008362 succinate buffer Substances 0.000 claims description 4
- 230000003432 anti-folate effect Effects 0.000 claims description 2
- 229940127074 antifolate Drugs 0.000 claims description 2
- 239000004052 folic acid antagonist Substances 0.000 claims description 2
- 102000006495 integrins Human genes 0.000 claims description 2
- 108010044426 integrins Proteins 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 102000005962 receptors Human genes 0.000 claims description 2
- 108020003175 receptors Proteins 0.000 claims description 2
- 229960004641 rituximab Drugs 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 231100000167 toxic agent Toxicity 0.000 claims description 2
- 239000003440 toxic substance Substances 0.000 claims description 2
- 229960000575 trastuzumab Drugs 0.000 claims description 2
- 239000006172 buffering agent Substances 0.000 claims 1
- 238000013467 fragmentation Methods 0.000 claims 1
- 238000006062 fragmentation reaction Methods 0.000 claims 1
- 238000010791 quenching Methods 0.000 claims 1
- 230000000171 quenching effect Effects 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- 229920001213 Polysorbate 20 Polymers 0.000 description 3
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 3
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 3
- FUHCFUVCWLZEDQ-UHFFFAOYSA-N 1-(2,5-dioxopyrrolidin-1-yl)oxy-1-oxo-4-(pyridin-2-yldisulfanyl)butane-2-sulfonic acid Chemical compound O=C1CCC(=O)N1OC(=O)C(S(=O)(=O)O)CCSSC1=CC=CC=N1 FUHCFUVCWLZEDQ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 238000005377 adsorption chromatography Methods 0.000 description 2
- 125000003275 alpha amino acid group Chemical group 0.000 description 2
- 230000021615 conjugation Effects 0.000 description 2
- 238000009295 crossflow filtration Methods 0.000 description 2
- 229940068977 polysorbate 20 Drugs 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012537 formulation buffer Substances 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011535 reaction buffer Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 229960003080 taurine Drugs 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201462081914P | 2014-11-19 | 2014-11-19 | |
| US62/081,914 | 2014-11-19 | ||
| PCT/US2015/061310 WO2016081584A1 (en) | 2014-11-19 | 2015-11-18 | Process for preparing cell-binding agent-cytotoxic agent conjugates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018505128A JP2018505128A (ja) | 2018-02-22 |
| JP2018505128A5 true JP2018505128A5 (enExample) | 2018-12-27 |
Family
ID=54754814
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017525940A Ceased JP2018505128A (ja) | 2014-11-19 | 2015-11-18 | 細胞結合剤−細胞毒性剤コンジュゲートを調製するためのプロセス |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US10413615B2 (enExample) |
| EP (1) | EP3220959A1 (enExample) |
| JP (1) | JP2018505128A (enExample) |
| KR (1) | KR20170088905A (enExample) |
| CN (1) | CN107592813A (enExample) |
| AU (1) | AU2015349985A1 (enExample) |
| CA (1) | CA2966932A1 (enExample) |
| IL (1) | IL251900B (enExample) |
| MA (1) | MA40934A (enExample) |
| RU (1) | RU2711930C2 (enExample) |
| SG (1) | SG11201703599VA (enExample) |
| WO (1) | WO2016081584A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA3146385A1 (en) | 2019-07-10 | 2021-01-14 | Cybrexa 3, Inc. | Peptide conjugates of microtubule-targeting agents as therapeutics |
| CA3146560A1 (en) | 2019-07-10 | 2021-01-14 | Cybrexa 2, Inc. | Peptide conjugates of cytotoxins as therapeutics |
Family Cites Families (55)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4307016A (en) | 1978-03-24 | 1981-12-22 | Takeda Chemical Industries, Ltd. | Demethyl maytansinoids |
| US4256746A (en) | 1978-11-14 | 1981-03-17 | Takeda Chemical Industries | Dechloromaytansinoids, their pharmaceutical compositions and method of use |
| JPS55102583A (en) | 1979-01-31 | 1980-08-05 | Takeda Chem Ind Ltd | 20-acyloxy-20-demethylmaytansinoid compound |
| JPS55162791A (en) | 1979-06-05 | 1980-12-18 | Takeda Chem Ind Ltd | Antibiotic c-15003pnd and its preparation |
| JPS5645483A (en) | 1979-09-19 | 1981-04-25 | Takeda Chem Ind Ltd | C-15003phm and its preparation |
| JPS5645485A (en) | 1979-09-21 | 1981-04-25 | Takeda Chem Ind Ltd | Production of c-15003pnd |
| EP0028683A1 (en) | 1979-09-21 | 1981-05-20 | Takeda Chemical Industries, Ltd. | Antibiotic C-15003 PHO and production thereof |
| WO1982001188A1 (en) | 1980-10-08 | 1982-04-15 | Takeda Chemical Industries Ltd | 4,5-deoxymaytansinoide compounds and process for preparing same |
| US4450254A (en) | 1980-11-03 | 1984-05-22 | Standard Oil Company | Impact improvement of high nitrile resins |
| US4313946A (en) | 1981-01-27 | 1982-02-02 | The United States Of America As Represented By The Secretary Of Agriculture | Chemotherapeutically active maytansinoids from Trewia nudiflora |
| US4315929A (en) | 1981-01-27 | 1982-02-16 | The United States Of America As Represented By The Secretary Of Agriculture | Method of controlling the European corn borer with trewiasine |
| JPS57192389A (en) | 1981-05-20 | 1982-11-26 | Takeda Chem Ind Ltd | Novel maytansinoid |
| GB8607679D0 (en) | 1986-03-27 | 1986-04-30 | Winter G P | Recombinant dna product |
| US5225539A (en) | 1986-03-27 | 1993-07-06 | Medical Research Council | Recombinant altered antibodies and methods of making altered antibodies |
| US5530101A (en) | 1988-12-28 | 1996-06-25 | Protein Design Labs, Inc. | Humanized immunoglobulins |
| GB9015198D0 (en) | 1990-07-10 | 1990-08-29 | Brien Caroline J O | Binding substance |
| DK0546073T3 (da) | 1990-08-29 | 1998-02-02 | Genpharm Int | Frembringelse og anvendelse af transgene, ikke-humane dyr, der er i stand til at danne heterologe antistoffer |
| US5545806A (en) | 1990-08-29 | 1996-08-13 | Genpharm International, Inc. | Ransgenic non-human animals for producing heterologous antibodies |
| SE9102074D0 (sv) | 1991-07-03 | 1991-07-03 | Kabi Pharmacia Ab | Tomour antigen specific antibody |
| ES2341666T3 (es) | 1991-12-02 | 2010-06-24 | Medimmune Limited | Produccion de autoanticuerpos de repertorios de segmentos de anticue rpos expresados en la superficie de fagos. |
| CA2076465C (en) | 1992-03-25 | 2002-11-26 | Ravi V. J. Chari | Cell binding agent conjugates of analogues and derivatives of cc-1065 |
| US5639641A (en) | 1992-09-09 | 1997-06-17 | Immunogen Inc. | Resurfacing of rodent antibodies |
| IL111748A0 (en) | 1993-12-03 | 1995-01-24 | Zeneca Ltd | Proteins |
| US6265150B1 (en) | 1995-06-07 | 2001-07-24 | Becton Dickinson & Company | Phage antibodies |
| US5714352A (en) | 1996-03-20 | 1998-02-03 | Xenotech Incorporated | Directed switch-mediated DNA recombination |
| US5958872A (en) | 1996-04-01 | 1999-09-28 | Apoptosis Technology, Inc. | Active survival domains of IGF-IR and methods of use |
| EP1005569A2 (en) | 1997-08-01 | 2000-06-07 | MorphoSys AG | Novel method and phage for the identification of nucleic acid sequences encoding members of a multimeric (poly)peptide complex |
| TW593241B (en) | 1999-04-20 | 2004-06-21 | Hoffmann La Roche | Carbamic acid derivatives |
| EP1257289A1 (en) | 2000-02-08 | 2002-11-20 | The Penn State Research Foundation | Immunotherapy using interleukin 13 receptor subunit alpha 2 |
| US6333410B1 (en) | 2000-08-18 | 2001-12-25 | Immunogen, Inc. | Process for the preparation and purification of thiol-containing maytansinoids |
| US6596503B1 (en) | 2000-08-18 | 2003-07-22 | East Carolina University | Monoclonal antibody DS6, tumor-associated antigen CA6, and methods of use thereof |
| EP1399483B1 (en) | 2001-01-05 | 2010-04-14 | Pfizer Inc. | Antibodies to insulin-like growth factor i receptor |
| MXPA05004712A (es) | 2002-11-07 | 2005-11-23 | Immunogen Inc | Anticuerpos anti-cd33 y metodo para tratamiento de leucemia mieloide aguda utilizando los mismos. |
| WO2005010151A2 (en) | 2003-06-27 | 2005-02-03 | Abgenix, Inc | Antibodies directed to the deletion mutants of epidermal growth factor receptor and uses thereof |
| CN114053429A (zh) | 2004-06-01 | 2022-02-18 | 健泰科生物技术公司 | 抗体-药物偶联物和方法 |
| US20060045877A1 (en) | 2004-08-30 | 2006-03-02 | Goldmakher Viktor S | Immunoconjugates targeting syndecan-1 expressing cells and use thereof |
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| AU2006247039B2 (en) * | 2005-05-19 | 2011-03-03 | Amgen Inc. | Compositions and methods for increasing the stability of antibodies |
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| RU2595424C2 (ru) * | 2009-06-03 | 2016-08-27 | Иммьюноджен, Инк. | Способы конъюгации |
| AR078471A1 (es) | 2009-10-02 | 2011-11-09 | Sanofi Aventis | COMPUESTOS MAITANSINOIDES Y EL USO DE ESTOS PARA PREPARAR CONJUGADOS CON UN ANTICUERPO LOS CUALES SE UTILIZAN COMO AGENTES ANTICANCERIGENOS Y EL PROCEDIMIENTO DE PREPARACIoN DE ESTOS CONJUGADOS |
| AR078470A1 (es) | 2009-10-02 | 2011-11-09 | Sanofi Aventis | Anticuerpos que se unen especificamente al receptor epha2 |
| EP3196212B1 (en) | 2010-02-24 | 2020-06-03 | ImmunoGen, Inc. | Immunoconjugates comprising a folate receptor 1 antibody |
| SI2544719T1 (sl) | 2010-03-12 | 2019-11-29 | Debiopharm Int Sa | CD37-povezovalne molekule in njihovi imunokonjugati |
| WO2012019024A2 (en) | 2010-08-04 | 2012-02-09 | Immunogen, Inc. | Her3-binding molecules and immunoconjugates thereof |
| US9260483B2 (en) | 2011-01-10 | 2016-02-16 | Technische Universität München | Triazacyclononane-based phosphinate ligand and its use for molecular imaging |
| CN113896731A (zh) * | 2011-02-15 | 2022-01-07 | 伊缪诺金公司 | 细胞毒性苯并二氮杂䓬衍生物 |
| US20120282282A1 (en) * | 2011-04-04 | 2012-11-08 | Immunogen, Inc. | Methods for Decreasing Ocular Toxicity of Antibody Drug Conjugates |
| US9999680B2 (en) * | 2013-02-28 | 2018-06-19 | Immunogen, Inc. | Conjugates comprising cell-binding agents and maytansinoids as cytotoxic agents |
| US9498532B2 (en) * | 2013-03-13 | 2016-11-22 | Novartis Ag | Antibody drug conjugates |
| JP2019510741A (ja) * | 2016-02-05 | 2019-04-18 | イミュノジェン・インコーポレーテッド | 細胞結合剤・細胞毒性剤コンジュゲートを調製するための効率的なプロセス |
| KR20200108843A (ko) * | 2018-01-12 | 2020-09-21 | 이뮤노젠 아이엔씨 | 항체 약물 접합, 정제, 및 제제화 방법 |
-
2015
- 2015-11-18 WO PCT/US2015/061310 patent/WO2016081584A1/en not_active Ceased
- 2015-11-18 AU AU2015349985A patent/AU2015349985A1/en not_active Abandoned
- 2015-11-18 MA MA040934A patent/MA40934A/fr unknown
- 2015-11-18 CA CA2966932A patent/CA2966932A1/en not_active Abandoned
- 2015-11-18 EP EP15802310.1A patent/EP3220959A1/en not_active Withdrawn
- 2015-11-18 SG SG11201703599VA patent/SG11201703599VA/en unknown
- 2015-11-18 KR KR1020177016749A patent/KR20170088905A/ko not_active Withdrawn
- 2015-11-18 RU RU2017115812A patent/RU2711930C2/ru active
- 2015-11-18 CN CN201580060700.2A patent/CN107592813A/zh active Pending
- 2015-11-18 US US15/527,525 patent/US10413615B2/en not_active Expired - Fee Related
- 2015-11-18 JP JP2017525940A patent/JP2018505128A/ja not_active Ceased
-
2017
- 2017-04-25 IL IL251900A patent/IL251900B/en not_active IP Right Cessation
-
2019
- 2019-08-07 US US16/534,521 patent/US20200101168A1/en not_active Abandoned
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