JP2016534990A5 - - Google Patents
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- JP2016534990A5 JP2016534990A5 JP2016522097A JP2016522097A JP2016534990A5 JP 2016534990 A5 JP2016534990 A5 JP 2016534990A5 JP 2016522097 A JP2016522097 A JP 2016522097A JP 2016522097 A JP2016522097 A JP 2016522097A JP 2016534990 A5 JP2016534990 A5 JP 2016534990A5
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- Japan
- Prior art keywords
- ligand
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- drug
- alkyl
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- Prior art date
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- 239000003814 drug Substances 0.000 claims description 215
- 229940079593 drug Drugs 0.000 claims description 214
- 150000001875 compounds Chemical class 0.000 claims description 117
- 239000003446 ligand Substances 0.000 claims description 88
- 229920001223 polyethylene glycol Polymers 0.000 claims description 72
- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 239000002202 Polyethylene glycol Substances 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 22
- -1 amino aldehyde Chemical group 0.000 claims description 20
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 235000001014 amino acid Nutrition 0.000 claims description 14
- 150000001413 amino acids Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims description 10
- 125000003827 glycol group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 10
- 229920000768 polyamine Chemical group 0.000 claims description 10
- 150000001414 amino alcohols Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 150000003573 thiols Chemical group 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 7
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000000732 arylene group Chemical group 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 4
- 239000000427 antigen Substances 0.000 claims description 4
- 102000036639 antigens Human genes 0.000 claims description 4
- 108091007433 antigens Proteins 0.000 claims description 4
- 108010044540 auristatin Proteins 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 150000008134 glucuronides Chemical group 0.000 claims description 3
- 230000002209 hydrophobic effect Effects 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 102000004225 Cathepsin B Human genes 0.000 claims description 2
- 108090000712 Cathepsin B Proteins 0.000 claims description 2
- 102000005744 Glycoside Hydrolases Human genes 0.000 claims description 2
- 108010031186 Glycoside Hydrolases Proteins 0.000 claims description 2
- 125000006242 amine protecting group Chemical group 0.000 claims description 2
- 125000002837 carbocyclic group Chemical group 0.000 claims description 2
- 238000003776 cleavage reaction 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
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 125000006850 spacer group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000000562 conjugate Substances 0.000 description 93
- 125000004429 atom Chemical group 0.000 description 10
- 0 C*(C*)(NC(CS*)C(C)=O)S Chemical compound C*(C*)(NC(CS*)C(C)=O)S 0.000 description 6
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 3
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 3
- 235000018417 cysteine Nutrition 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- LJRDOKAZOAKLDU-UDXJMMFXSA-N (2s,3s,4r,5r,6r)-5-amino-2-(aminomethyl)-6-[(2r,3s,4r,5s)-5-[(1r,2r,3s,5r,6s)-3,5-diamino-2-[(2s,3r,4r,5s,6r)-3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-hydroxycyclohexyl]oxy-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyoxane-3,4-diol;sulfuric ac Chemical compound OS(O)(=O)=O.N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO LJRDOKAZOAKLDU-UDXJMMFXSA-N 0.000 description 1
- 102100024222 B-lymphocyte antigen CD19 Human genes 0.000 description 1
- 102100022005 B-lymphocyte antigen CD20 Human genes 0.000 description 1
- 102100025221 CD70 antigen Human genes 0.000 description 1
- XUJNEKJLAYXESH-UWTATZPHSA-N D-Cysteine Chemical compound SC[C@@H](N)C(O)=O XUJNEKJLAYXESH-UWTATZPHSA-N 0.000 description 1
- KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 description 1
- VVNCNSJFMMFHPL-VKHMYHEASA-N D-penicillamine Chemical compound CC(C)(S)[C@@H](N)C(O)=O VVNCNSJFMMFHPL-VKHMYHEASA-N 0.000 description 1
- 229930195710 D‐cysteine Natural products 0.000 description 1
- 101000980825 Homo sapiens B-lymphocyte antigen CD19 Proteins 0.000 description 1
- 101000897405 Homo sapiens B-lymphocyte antigen CD20 Proteins 0.000 description 1
- 101000934356 Homo sapiens CD70 antigen Proteins 0.000 description 1
- 101000934338 Homo sapiens Myeloid cell surface antigen CD33 Proteins 0.000 description 1
- 101000851376 Homo sapiens Tumor necrosis factor receptor superfamily member 8 Proteins 0.000 description 1
- 235000019766 L-Lysine Nutrition 0.000 description 1
- 239000004201 L-cysteine Substances 0.000 description 1
- 235000013878 L-cysteine Nutrition 0.000 description 1
- VVNCNSJFMMFHPL-GSVOUGTGSA-N L-penicillamine Chemical compound CC(C)(S)[C@H](N)C(O)=O VVNCNSJFMMFHPL-GSVOUGTGSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 102100025243 Myeloid cell surface antigen CD33 Human genes 0.000 description 1
- 102100036857 Tumor necrosis factor receptor superfamily member 8 Human genes 0.000 description 1
- 239000000611 antibody drug conjugate Substances 0.000 description 1
- 229940049595 antibody-drug conjugate Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 235000018977 lysine Nutrition 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229960001639 penicillamine Drugs 0.000 description 1
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361891320P | 2013-10-15 | 2013-10-15 | |
| US61/891,320 | 2013-10-15 | ||
| US201461941904P | 2014-02-19 | 2014-02-19 | |
| US61/941,904 | 2014-02-19 | ||
| US201461947742P | 2014-03-04 | 2014-03-04 | |
| US61/947,742 | 2014-03-04 | ||
| US201461975318P | 2014-04-04 | 2014-04-04 | |
| US61/975,318 | 2014-04-04 | ||
| PCT/US2014/060477 WO2015057699A2 (en) | 2013-10-15 | 2014-10-14 | Pegylated drug-linkers for improved ligand-drug conjugate pharmacokinetics |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019194539A Division JP2020012002A (ja) | 2013-10-15 | 2019-10-25 | 改善されたリガンド−薬物コンジュゲート薬物動態のためのｐｅｇ化薬物−リンカー |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016534990A JP2016534990A (ja) | 2016-11-10 |
| JP2016534990A5 true JP2016534990A5 (enExample) | 2017-11-24 |
| JP6747971B2 JP6747971B2 (ja) | 2020-08-26 |
Family
ID=52828847
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016522097A Active JP6747971B2 (ja) | 2013-10-15 | 2014-10-14 | 改善されたリガンド−薬物コンジュゲート薬物動態のためのｐｅｇ化薬物−リンカー |
| JP2019194539A Withdrawn JP2020012002A (ja) | 2013-10-15 | 2019-10-25 | 改善されたリガンド−薬物コンジュゲート薬物動態のためのｐｅｇ化薬物−リンカー |
| JP2022005005A Active JP7330309B2 (ja) | 2013-10-15 | 2022-01-17 | 改善されたリガンド－薬物コンジュゲート薬物動態のためのｐｅｇ化薬物－リンカー |
| JP2023104167A Pending JP2023116821A (ja) | 2013-10-15 | 2023-06-26 | 改善されたリガンド－薬物コンジュゲート薬物動態のためのｐｅｇ化薬物－リンカー |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019194539A Withdrawn JP2020012002A (ja) | 2013-10-15 | 2019-10-25 | 改善されたリガンド−薬物コンジュゲート薬物動態のためのｐｅｇ化薬物−リンカー |
| JP2022005005A Active JP7330309B2 (ja) | 2013-10-15 | 2022-01-17 | 改善されたリガンド－薬物コンジュゲート薬物動態のためのｐｅｇ化薬物－リンカー |
| JP2023104167A Pending JP2023116821A (ja) | 2013-10-15 | 2023-06-26 | 改善されたリガンド－薬物コンジュゲート薬物動態のためのｐｅｇ化薬物－リンカー |
Country Status (23)
| Country | Link |
|---|---|
| US (3) | US11103593B2 (enExample) |
| EP (2) | EP3057585B1 (enExample) |
| JP (4) | JP6747971B2 (enExample) |
| KR (4) | KR102356814B1 (enExample) |
| CN (1) | CN105764503A (enExample) |
| AU (3) | AU2014337555C1 (enExample) |
| BR (1) | BR112016007622A2 (enExample) |
| CA (2) | CA2921707C (enExample) |
| CY (1) | CY1123675T1 (enExample) |
| DK (1) | DK3057585T3 (enExample) |
| EA (1) | EA201690780A1 (enExample) |
| ES (1) | ES2826398T3 (enExample) |
| HU (1) | HUE051389T2 (enExample) |
| IL (4) | IL293071A (enExample) |
| MX (4) | MX385458B (enExample) |
| NZ (2) | NZ758050A (enExample) |
| PL (1) | PL3057585T3 (enExample) |
| PT (1) | PT3057585T (enExample) |
| SG (3) | SG10201806917PA (enExample) |
| SI (1) | SI3057585T1 (enExample) |
| TW (4) | TWI736047B (enExample) |
| WO (1) | WO2015057699A2 (enExample) |
| ZA (1) | ZA201601436B (enExample) |
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| NZ758050A (en) | 2013-10-15 | 2024-03-22 | Seagen Inc | Pegylated drug-linkers for improved ligand-drug conjugate pharmacokinetics |
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| WO2016059377A1 (en) | 2014-10-14 | 2016-04-21 | Polytherics Limited | Process for the conjugation of a peptide or protein with a reagent comprising a leaving group including a portion of peg |
| EP3220956B1 (en) * | 2014-10-24 | 2023-08-09 | Abzena (UK) Limited | Conjugates and conjugating reagents |
| US11566082B2 (en) | 2014-11-17 | 2023-01-31 | Cytiva Bioprocess R&D Ab | Mutated immunoglobulin-binding polypeptides |
| CA2976740A1 (en) * | 2015-03-18 | 2016-09-22 | Seattle Genetics, Inc. | Cd48 antibodies and conjugates thereof |
| EP3165237B1 (en) | 2015-11-03 | 2018-12-19 | Industrial Technology Research Institute | Antibody-drug conjugate (adc) and method for forming the same |
| KR102847348B1 (ko) | 2015-11-25 | 2025-08-19 | 주식회사 리가켐바이오사이언스 | 펩타이드 그룹을 포함하는 접합체 및 이와 관련된 제조방법 |
| US11173214B2 (en) | 2015-11-25 | 2021-11-16 | Legochem Biosciences, Inc. | Antibody-drug conjugates comprising branched linkers and methods related thereto |
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| EP3455243B1 (en) | 2016-05-11 | 2021-03-24 | Cytiva BioProcess R&D AB | Separation matrix |
| US10730908B2 (en) | 2016-05-11 | 2020-08-04 | Ge Healthcare Bioprocess R&D Ab | Separation method |
| US10703774B2 (en) | 2016-09-30 | 2020-07-07 | Ge Healthcare Bioprocess R&D Ab | Separation method |
| US10654887B2 (en) | 2016-05-11 | 2020-05-19 | Ge Healthcare Bio-Process R&D Ab | Separation matrix |
| SG11201900699QA (en) | 2016-08-09 | 2019-02-27 | Seattle Genetics Inc | Drug conjugates with self-stabilizing linkers having improved physiochemical properties |
| US12448411B2 (en) | 2016-09-30 | 2025-10-21 | Cytiva Bioprocess R&D Ab | Separation method |
| EP3525826B1 (en) | 2016-10-11 | 2020-07-22 | Byondis B.V | Non-linear self-immolative linkers and conjugates thereof |
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| JP7244987B2 (ja) * | 2016-12-14 | 2023-03-23 | シージェン インコーポレイテッド | 多剤抗体薬物コンジュゲート |
| BR112019013107A2 (pt) | 2016-12-22 | 2019-12-17 | Univ Degli Studi Magna Graecia Catanzaro | anticorpos, molécula de ligação, receptor de antígeno quimérico, vetor de expressão, composição farmacêutica, linfócito, ácido nucleico, célula de hibridoma, método para a produção do anticorpo monoclonal e usos |
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