JP2017503777A5 - - Google Patents
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- JP2017503777A5 JP2017503777A5 JP2016540522A JP2016540522A JP2017503777A5 JP 2017503777 A5 JP2017503777 A5 JP 2017503777A5 JP 2016540522 A JP2016540522 A JP 2016540522A JP 2016540522 A JP2016540522 A JP 2016540522A JP 2017503777 A5 JP2017503777 A5 JP 2017503777A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- independently selected
- nhc
- linked
- substituted
- 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
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- 150000001875 compounds Chemical class 0.000 claims 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 18
- 125000005842 heteroatom Chemical group 0.000 claims 17
- 229940127121 immunoconjugate Drugs 0.000 claims 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000001424 substituent group Chemical group 0.000 claims 10
- 125000006580 bicyclic heterocycloalkyl group Chemical group 0.000 claims 9
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 125000002883 imidazolyl group Chemical group 0.000 claims 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 2
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 2
- 239000004475 Arginine Substances 0.000 claims 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 2
- 108010016626 Dipeptides Proteins 0.000 claims 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 2
- 239000004471 Glycine Substances 0.000 claims 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 2
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 claims 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 2
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 2
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 2
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 2
- 239000004472 Lysine Substances 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 2
- 239000004473 Threonine Substances 0.000 claims 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 2
- 235000004279 alanine Nutrition 0.000 claims 2
- 235000001014 amino acid Nutrition 0.000 claims 2
- 229940024606 amino acid Drugs 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 2
- 235000009582 asparagine Nutrition 0.000 claims 2
- 229960001230 asparagine Drugs 0.000 claims 2
- 235000003704 aspartic acid Nutrition 0.000 claims 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 2
- 235000018417 cysteine Nutrition 0.000 claims 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 2
- 235000013922 glutamic acid Nutrition 0.000 claims 2
- 239000004220 glutamic acid Substances 0.000 claims 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 2
- 229960000310 isoleucine Drugs 0.000 claims 2
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 2
- 229930182817 methionine Natural products 0.000 claims 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
- 125000006850 spacer group Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 2
- 239000004474 valine Substances 0.000 claims 2
- 239000000427 antigen Substances 0.000 claims 1
- 102000036639 antigens Human genes 0.000 claims 1
- 108091007433 antigens Proteins 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361917293P | 2013-12-17 | 2013-12-17 | |
| US61/917,293 | 2013-12-17 | ||
| PCT/US2014/070800 WO2015095301A2 (en) | 2013-12-17 | 2014-12-17 | Cytotoxic peptides and conjugates thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019176561A Division JP2020023514A (ja) | 2013-12-17 | 2019-09-27 | 細胞障害性ペプチドおよびその抱合体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017503777A JP2017503777A (ja) | 2017-02-02 |
| JP2017503777A5 true JP2017503777A5 (https=) | 2018-02-01 |
| JP6636925B2 JP6636925B2 (ja) | 2020-01-29 |
Family
ID=52463118
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016540522A Expired - Fee Related JP6636925B2 (ja) | 2013-12-17 | 2014-12-17 | 細胞障害性ペプチドおよびその抱合体 |
| JP2019176561A Pending JP2020023514A (ja) | 2013-12-17 | 2019-09-27 | 細胞障害性ペプチドおよびその抱合体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019176561A Pending JP2020023514A (ja) | 2013-12-17 | 2019-09-27 | 細胞障害性ペプチドおよびその抱合体 |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US9988420B2 (https=) |
| EP (2) | EP3082877B1 (https=) |
| JP (2) | JP6636925B2 (https=) |
| KR (1) | KR20160098257A (https=) |
| CN (1) | CN105899526A (https=) |
| AU (1) | AU2014364812B2 (https=) |
| BR (1) | BR112016012538A2 (https=) |
| CA (1) | CA2930614A1 (https=) |
| EA (1) | EA201691251A1 (https=) |
| ES (1) | ES2758506T3 (https=) |
| IL (1) | IL245558B (https=) |
| MX (1) | MX2016007865A (https=) |
| PL (1) | PL3082877T3 (https=) |
| PT (1) | PT3082877T (https=) |
| SG (1) | SG11201604877UA (https=) |
| WO (1) | WO2015095301A2 (https=) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
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| KR102447350B1 (ko) * | 2013-02-08 | 2022-09-23 | 노파르티스 아게 | 면역접합체의 제조를 위한 항체의 변형에 사용되는 특정 부위 |
| PL2968440T3 (pl) | 2013-03-15 | 2019-12-31 | Zymeworks Inc. | Związki cytotoksyczne i antymitotyczne oraz sposoby ich stosowania |
| RU2729194C2 (ru) | 2013-12-27 | 2020-08-05 | Займворкс Инк. | Сульфонамидсодержащие связывающие системы для лекарственных конъюгатов |
| AU2014373640B2 (en) | 2013-12-27 | 2018-08-30 | Var2 Pharmaceuticals Aps | VAR2CSA-drug conjugates |
| CA2940451A1 (en) * | 2014-03-12 | 2015-09-17 | Novartis Ag | Specific sites for modifying antibodies to make immunoconjugates |
| CN106573956A (zh) | 2014-06-13 | 2017-04-19 | 诺华股份有限公司 | 澳瑞他汀衍生物及其缀合物 |
| AU2015318556C1 (en) | 2014-09-17 | 2021-01-07 | Zymeworks Bc Inc. | Cytotoxic and anti-mitotic compounds, and methods of using the same |
| US11566082B2 (en) | 2014-11-17 | 2023-01-31 | Cytiva Bioprocess R&D Ab | Mutated immunoglobulin-binding polypeptides |
| US10703774B2 (en) | 2016-09-30 | 2020-07-07 | Ge Healthcare Bioprocess R&D Ab | Separation method |
| JP6987424B2 (ja) | 2016-05-11 | 2022-01-05 | サイティバ・バイオプロセス・アールアンドディ・アクチボラグ | 分離マトリックスを洗浄および／または消毒する方法 |
| US11708390B2 (en) | 2016-05-11 | 2023-07-25 | Cytiva Bioprocess R&D Ab | Method of storing a separation matrix |
| CN109071613A (zh) | 2016-05-11 | 2018-12-21 | 通用电气医疗集团生物工艺研发股份公司 | 分离基质 |
| US10730908B2 (en) | 2016-05-11 | 2020-08-04 | Ge Healthcare Bioprocess R&D Ab | Separation method |
| JP7031934B2 (ja) | 2016-05-11 | 2022-03-08 | サイティバ・バイオプロセス・アールアンドディ・アクチボラグ | 分離マトリックス |
| US10654887B2 (en) | 2016-05-11 | 2020-05-19 | Ge Healthcare Bio-Process R&D Ab | Separation matrix |
| US10889615B2 (en) | 2016-05-11 | 2021-01-12 | Cytiva Bioprocess R&D Ab | Mutated immunoglobulin-binding polypeptides |
| US12448411B2 (en) | 2016-09-30 | 2025-10-21 | Cytiva Bioprocess R&D Ab | Separation method |
| US10517958B2 (en) | 2016-10-04 | 2019-12-31 | Zymeworks Inc. | Compositions and methods for the treatment of platinum-drug resistant cancer |
| JOP20190187A1 (ar) | 2017-02-03 | 2019-08-01 | Novartis Ag | مترافقات عقار جسم مضاد لـ ccr7 |
| TW202014209A (zh) * | 2018-06-20 | 2020-04-16 | 瑞士商諾華公司 | 用於消融造血幹細胞之抗體藥物軛合物 |
| CN113365969B (zh) * | 2018-11-23 | 2023-09-15 | 上海药明合联生物技术有限公司 | 含有邻苯二甲醛的连接体及其用于制备抗体-药物缀合物的用途 |
| IL296277A (en) * | 2020-03-09 | 2022-11-01 | Sigma Aldrich Co Llc | Efficient preparation of dolstatin and oristatin analogs via a common intermediate |
| US20230181756A1 (en) | 2020-04-30 | 2023-06-15 | Novartis Ag | Ccr7 antibody drug conjugates for treating cancer |
| EP4279502A4 (en) * | 2021-01-18 | 2026-02-11 | Ajinomoto Kk | COMPOUND OR ITS SALT, AND ANTIBODIES THUS OBTAINED |
| WO2023061405A1 (zh) * | 2021-10-12 | 2023-04-20 | 成都科岭源医药技术有限公司 | 一种高稳定性的靶向接头-药物偶联物 |
| JP2025524986A (ja) * | 2022-07-27 | 2025-08-01 | メディボストン リミテッド | オーリスタチン誘導体およびそのコンジュゲート |
| WO2024152000A1 (en) * | 2023-01-13 | 2024-07-18 | The Trustees Of The University Of Pennsylvania | Disruptable linker compositions, switchable bispecific t cell nanoengager (switch-bite) compositions comprising the same, and methods of use thereof |
| AR132368A1 (es) | 2023-04-18 | 2025-06-18 | Astrazeneca Ab | Conjugados que comprenden enlazadores escindibles |
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-
2014
- 2014-12-17 BR BR112016012538A patent/BR112016012538A2/pt not_active Application Discontinuation
- 2014-12-17 KR KR1020167015935A patent/KR20160098257A/ko not_active Ceased
- 2014-12-17 WO PCT/US2014/070800 patent/WO2015095301A2/en not_active Ceased
- 2014-12-17 EA EA201691251A patent/EA201691251A1/ru unknown
- 2014-12-17 EP EP14835606.6A patent/EP3082877B1/en not_active Not-in-force
- 2014-12-17 ES ES14835606T patent/ES2758506T3/es active Active
- 2014-12-17 MX MX2016007865A patent/MX2016007865A/es active IP Right Grant
- 2014-12-17 CA CA2930614A patent/CA2930614A1/en not_active Abandoned
- 2014-12-17 AU AU2014364812A patent/AU2014364812B2/en not_active Ceased
- 2014-12-17 SG SG11201604877UA patent/SG11201604877UA/en unknown
- 2014-12-17 PL PL14835606T patent/PL3082877T3/pl unknown
- 2014-12-17 JP JP2016540522A patent/JP6636925B2/ja not_active Expired - Fee Related
- 2014-12-17 PT PT148356066T patent/PT3082877T/pt unknown
- 2014-12-17 CN CN201480068696.XA patent/CN105899526A/zh active Pending
- 2014-12-17 EP EP19193628.5A patent/EP3753578A1/en not_active Withdrawn
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2016
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2018
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2019
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- 2019-09-27 JP JP2019176561A patent/JP2020023514A/ja active Pending
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