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 (https=) | 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 (https=) |
| EP (1) | EP3220959A1 (https=) |
| JP (1) | JP2018505128A (https=) |
| KR (1) | KR20170088905A (https=) |
| CN (1) | CN107592813A (https=) |
| AU (1) | AU2015349985A1 (https=) |
| CA (1) | CA2966932A1 (https=) |
| IL (1) | IL251900B (https=) |
| MA (1) | MA40934A (https=) |
| RU (1) | RU2711930C2 (https=) |
| SG (1) | SG11201703599VA (https=) |
| WO (1) | WO2016081584A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2022000449A (es) | 2019-07-10 | 2022-04-25 | Cybrexa 2 Inc | Conjugados peptídicos de citotoxinas como terapéuticos. |
| US11555019B2 (en) | 2019-07-10 | 2023-01-17 | Cybrexa 3, Inc. | Peptide conjugates of microtubule-targeting agents as therapeutics |
Family Cites Families (55)
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| 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 |
| EP0028683A1 (en) | 1979-09-21 | 1981-05-20 | Takeda Chemical Industries, Ltd. | Antibiotic C-15003 PHO and production thereof |
| JPS5645485A (en) | 1979-09-21 | 1981-04-25 | Takeda Chem Ind Ltd | Production of c-15003pnd |
| 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 |
| 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 |
| 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 |
| JPS57192389A (en) | 1981-05-20 | 1982-11-26 | Takeda Chem Ind Ltd | Novel maytansinoid |
| US5225539A (en) | 1986-03-27 | 1993-07-06 | Medical Research Council | Recombinant altered antibodies and methods of making altered antibodies |
| GB8607679D0 (en) | 1986-03-27 | 1986-04-30 | Winter G P | Recombinant dna product |
| 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 |
| ATE158021T1 (de) | 1990-08-29 | 1997-09-15 | Genpharm Int | Produktion und nützung nicht-menschliche transgentiere zur produktion heterologe antikörper |
| 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 |
| PT1024191E (pt) | 1991-12-02 | 2008-12-22 | Medical Res Council | Produção de auto-anticorpos a partir de reportórios de segmentos de anticorpo e exibidos em fagos |
| EP0563475B1 (en) | 1992-03-25 | 2000-05-31 | Immunogen Inc | Cell binding agent conjugates of 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 |
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| WO1999006587A2 (en) | 1997-08-01 | 1999-02-11 | 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 |
| WO2001058479A1 (en) | 2000-02-08 | 2001-08-16 | The Penn State Research Foundation | Immunotherapy using interleukin 13 receptor subunit alpha 2 |
| US6596503B1 (en) | 2000-08-18 | 2003-07-22 | East Carolina University | Monoclonal antibody DS6, tumor-associated antigen CA6, and methods of use thereof |
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| ME00502B (me) | 2001-01-05 | 2011-10-10 | Amgen Fremont Inc | Antitjela za insulinu sličan receptor faktora i rasta |
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| US11274121B2 (en) * | 2018-01-12 | 2022-03-15 | Immunogen, Inc. | Methods for antibody drug conjugation, purification, and formulation |
-
2015
- 2015-11-18 US US15/527,525 patent/US10413615B2/en not_active Expired - Fee Related
- 2015-11-18 SG SG11201703599VA patent/SG11201703599VA/en unknown
- 2015-11-18 EP EP15802310.1A patent/EP3220959A1/en not_active Withdrawn
- 2015-11-18 KR KR1020177016749A patent/KR20170088905A/ko not_active Withdrawn
- 2015-11-18 CN CN201580060700.2A patent/CN107592813A/zh active Pending
- 2015-11-18 JP JP2017525940A patent/JP2018505128A/ja not_active Ceased
- 2015-11-18 AU AU2015349985A patent/AU2015349985A1/en not_active Abandoned
- 2015-11-18 RU RU2017115812A patent/RU2711930C2/ru active
- 2015-11-18 MA MA040934A patent/MA40934A/fr unknown
- 2015-11-18 CA CA2966932A patent/CA2966932A1/en not_active Abandoned
- 2015-11-18 WO PCT/US2015/061310 patent/WO2016081584A1/en 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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