JP2017512752A5 - - Google Patents
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- Publication number
- JP2017512752A5 JP2017512752A5 JP2016552268A JP2016552268A JP2017512752A5 JP 2017512752 A5 JP2017512752 A5 JP 2017512752A5 JP 2016552268 A JP2016552268 A JP 2016552268A JP 2016552268 A JP2016552268 A JP 2016552268A JP 2017512752 A5 JP2017512752 A5 JP 2017512752A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- optionally substituted
- solvate
- pharmaceutically acceptable
- drug
- 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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- 239000003446 ligand Substances 0.000 claims description 76
- 150000003839 salts Chemical class 0.000 claims description 60
- 150000001875 compounds Chemical class 0.000 claims description 59
- 239000012453 solvate Substances 0.000 claims description 58
- -1 substituted Chemical class 0.000 claims description 48
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 229940024606 amino acid Drugs 0.000 claims description 40
- 235000001014 amino acid Nutrition 0.000 claims description 40
- 150000001413 amino acids Chemical class 0.000 claims description 40
- 125000002947 alkylene group Chemical group 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 18
- 229940049906 glutamate Drugs 0.000 claims description 14
- 229930195712 glutamate Natural products 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 13
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 12
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims description 12
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims description 12
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims description 12
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims description 12
- 229960001230 asparagine Drugs 0.000 claims description 12
- 235000009582 asparagine Nutrition 0.000 claims description 12
- 235000004554 glutamine Nutrition 0.000 claims description 12
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims description 12
- 229960002743 glutamine Drugs 0.000 claims description 12
- 125000005647 linker group Chemical group 0.000 claims description 12
- 229960001153 serine Drugs 0.000 claims description 12
- 235000004400 serine Nutrition 0.000 claims description 12
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 11
- 229940079593 drug Drugs 0.000 claims description 11
- 239000004473 Threonine Substances 0.000 claims description 9
- 229960002898 threonine Drugs 0.000 claims description 9
- 239000004475 Arginine Substances 0.000 claims description 8
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 8
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims description 8
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 8
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims description 8
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 8
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 8
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 8
- 239000004472 Lysine Substances 0.000 claims description 8
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims description 8
- 229960003767 alanine Drugs 0.000 claims description 8
- 235000004279 alanine Nutrition 0.000 claims description 8
- 229960003121 arginine Drugs 0.000 claims description 8
- 235000009697 arginine Nutrition 0.000 claims description 8
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 8
- 229940009098 aspartate Drugs 0.000 claims description 8
- 235000014304 histidine Nutrition 0.000 claims description 8
- 229960002885 histidine Drugs 0.000 claims description 8
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 8
- 235000018977 lysine Nutrition 0.000 claims description 8
- 229960003646 lysine Drugs 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 235000008521 threonine Nutrition 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 7
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 6
- 208000023275 Autoimmune disease Diseases 0.000 claims description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 6
- JRQLTSHRMXYCEB-VKHMYHEASA-N (2S)-2-(2H-triazol-4-ylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC=1C=NNN=1 JRQLTSHRMXYCEB-VKHMYHEASA-N 0.000 claims description 4
- WMXUAKCTYHRPBT-BYPYZUCNSA-N (2s)-2-(1h-pyrazol-5-ylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC=1C=CNN=1 WMXUAKCTYHRPBT-BYPYZUCNSA-N 0.000 claims description 4
- UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 claims description 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- CZWARROQQFCFJB-UHFFFAOYSA-N L-2-Amino-5-hydroxypentanoic acid Chemical compound OC(=O)C(N)CCCO CZWARROQQFCFJB-UHFFFAOYSA-N 0.000 claims description 4
- UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 claims description 4
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 4
- CKLJMWTZIZZHCS-REOHCLBHSA-L aspartate group Chemical group N[C@@H](CC(=O)[O-])C(=O)[O-] CKLJMWTZIZZHCS-REOHCLBHSA-L 0.000 claims description 4
- 235000003704 aspartic acid Nutrition 0.000 claims description 4
- 229960005261 aspartic acid Drugs 0.000 claims description 4
- 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 description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 235000013922 glutamic acid Nutrition 0.000 claims description 4
- 239000004220 glutamic acid Substances 0.000 claims description 4
- 229960002989 glutamic acid Drugs 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 4
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 4
- 229960002317 succinimide Drugs 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 208000035473 Communicable disease Diseases 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000004471 Glycine Substances 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 108010044540 auristatin Proteins 0.000 claims description 2
- 230000037396 body weight Effects 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 108091005601 modified peptides Proteins 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229920001184 polypeptide Polymers 0.000 claims description 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 2
- 235000018102 proteins Nutrition 0.000 claims description 2
- 108090000623 proteins and genes Proteins 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 claims description 2
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- PECYZEOJVXMISF-UHFFFAOYSA-N 3-aminoalanine Chemical compound [NH3+]CC(N)C([O-])=O PECYZEOJVXMISF-UHFFFAOYSA-N 0.000 claims 1
- 0 CNC(*)C(NCC(*)NC([C@](CCC(O)=O)N[S+])=O)=O Chemical compound CNC(*)C(NCC(*)NC([C@](CCC(O)=O)N[S+])=O)=O 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461940759P | 2014-02-17 | 2014-02-17 | |
| US61/940,759 | 2014-02-17 | ||
| US201461947368P | 2014-03-03 | 2014-03-03 | |
| US61/947,368 | 2014-03-03 | ||
| PCT/US2015/016185 WO2015123679A1 (en) | 2014-02-17 | 2015-02-17 | Hydrophilic antibody-drug conjugates |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020024690A Division JP2020073607A (ja) | 2014-02-17 | 2020-02-17 | 親水性抗体−薬物コンジュゲート |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017512752A JP2017512752A (ja) | 2017-05-25 |
| JP2017512752A5 true JP2017512752A5 (OSRAM) | 2018-01-25 |
| JP6716461B2 JP6716461B2 (ja) | 2020-07-01 |
Family
ID=53800705
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016552268A Active JP6716461B2 (ja) | 2014-02-17 | 2015-02-17 | 親水性抗体−薬物コンジュゲート |
| JP2020024690A Withdrawn JP2020073607A (ja) | 2014-02-17 | 2020-02-17 | 親水性抗体−薬物コンジュゲート |
| JP2022078761A Active JP7447183B2 (ja) | 2014-02-17 | 2022-05-12 | 親水性抗体－薬物コンジュゲート |
| JP2022194229A Pending JP2023018157A (ja) | 2014-02-17 | 2022-12-05 | 親水性抗体－薬物コンジュゲート |
| JP2024075020A Pending JP2024096335A (ja) | 2014-02-17 | 2024-05-06 | 親水性抗体－薬物コンジュゲート |
Family Applications After (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020024690A Withdrawn JP2020073607A (ja) | 2014-02-17 | 2020-02-17 | 親水性抗体−薬物コンジュゲート |
| JP2022078761A Active JP7447183B2 (ja) | 2014-02-17 | 2022-05-12 | 親水性抗体－薬物コンジュゲート |
| JP2022194229A Pending JP2023018157A (ja) | 2014-02-17 | 2022-12-05 | 親水性抗体－薬物コンジュゲート |
| JP2024075020A Pending JP2024096335A (ja) | 2014-02-17 | 2024-05-06 | 親水性抗体－薬物コンジュゲート |
Country Status (14)
| Country | Link |
|---|---|
| US (4) | US10933112B2 (OSRAM) |
| EP (2) | EP3912641B1 (OSRAM) |
| JP (5) | JP6716461B2 (OSRAM) |
| KR (3) | KR20160120777A (OSRAM) |
| CN (1) | CN106029083B (OSRAM) |
| AU (3) | AU2015218202B2 (OSRAM) |
| CA (1) | CA2937753A1 (OSRAM) |
| EA (1) | EA201691650A1 (OSRAM) |
| ES (2) | ES2994375T3 (OSRAM) |
| IL (4) | IL290116B2 (OSRAM) |
| MX (2) | MX385823B (OSRAM) |
| SG (2) | SG10202001468UA (OSRAM) |
| WO (1) | WO2015123679A1 (OSRAM) |
| ZA (1) | ZA201605111B (OSRAM) |
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| JP7224365B2 (ja) * | 2017-06-19 | 2023-02-17 | バイリ－バイオ（チェンドゥ）ファーマスーティカル シーオー．，エルティーディー． | 酸性自己安定化ジョイントを有する抗体薬物複合体 |
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| TWI838358B (zh) | 2018-02-20 | 2024-04-11 | 美商思進公司 | 疏水性奧瑞他汀(auristatin)f化合物及其結合物 |
| IL322895A (en) | 2018-06-05 | 2025-10-01 | King S College London | Btnl3/8-targeted constructs for delivery of cargo to the digestive system |
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| TW202320857A (zh) | 2021-07-06 | 2023-06-01 | 美商普方生物製藥美國公司 | 連接子、藥物連接子及其結合物及其使用方法 |
| US11806405B1 (en) | 2021-07-19 | 2023-11-07 | Zeno Management, Inc. | Immunoconjugates and methods |
| EP4400121A1 (en) | 2021-09-03 | 2024-07-17 | Toray Industries, Inc. | Pharmaceutical composition for treating and/or preventing cancer |
| MX2024005831A (es) * | 2021-11-15 | 2024-07-09 | Systimmune Inc | Conjugado de anticuerpo biespecifico-farmaco de camptotecina y uso farmaceutico del mismo. |
| EP4433096A1 (en) | 2021-11-19 | 2024-09-25 | Ardeagen Corporation | Gpc3 binding agents, conjugates thereof and methods of using the same |
| IL313262A (en) * | 2021-12-03 | 2024-08-01 | Systimmune Inc | Anti-human trop2 antibody-camptothecin drug conjugate and medical use thereof |
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| EP3912641B1 (en) * | 2014-02-17 | 2024-11-06 | Seagen Inc. | Hydrophilic drug-linker compounds |
| CA3155093A1 (en) | 2019-09-19 | 2021-03-25 | Seagen Inc. | Selective drug release from internalized conjugates of biologically active compounds |
| JP2024511360A (ja) | 2021-03-18 | 2024-03-13 | シージェン インコーポレイテッド | 生体活性化合物の内部移行複合体からの選択的薬物放出 |
| US12036286B2 (en) | 2021-03-18 | 2024-07-16 | Seagen Inc. | Selective drug release from internalized conjugates of biologically active compounds |
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2015
- 2015-02-17 EP EP21168364.4A patent/EP3912641B1/en active Active
- 2015-02-17 ES ES21168364T patent/ES2994375T3/es active Active
- 2015-02-17 WO PCT/US2015/016185 patent/WO2015123679A1/en not_active Ceased
- 2015-02-17 EP EP15748980.8A patent/EP3107557B1/en active Active
- 2015-02-17 KR KR1020167025612A patent/KR20160120777A/ko not_active Ceased
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- 2015-02-17 US US15/118,031 patent/US10933112B2/en active Active
- 2015-02-17 IL IL290116A patent/IL290116B2/en unknown
- 2015-02-17 KR KR1020247007857A patent/KR20240036143A/ko not_active Withdrawn
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- 2015-02-17 ES ES15748980T patent/ES2885686T3/es active Active
- 2015-02-17 EA EA201691650A patent/EA201691650A1/ru unknown
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- 2015-02-17 KR KR1020237014278A patent/KR102647074B1/ko active Active
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- 2015-02-17 JP JP2016552268A patent/JP6716461B2/ja active Active
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- 2015-02-17 CA CA2937753A patent/CA2937753A1/en active Pending
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2016
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- 2016-07-28 MX MX2021010550A patent/MX2021010550A/es unknown
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2020
- 2020-02-17 JP JP2020024690A patent/JP2020073607A/ja not_active Withdrawn
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- 2022-05-12 JP JP2022078761A patent/JP7447183B2/ja active Active
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2023
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