JPWO2019236954A5 - - Google Patents
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- JPWO2019236954A5 JPWO2019236954A5 JP2020567763A JP2020567763A JPWO2019236954A5 JP WO2019236954 A5 JPWO2019236954 A5 JP WO2019236954A5 JP 2020567763 A JP2020567763 A JP 2020567763A JP 2020567763 A JP2020567763 A JP 2020567763A JP WO2019236954 A5 JPWO2019236954 A5 JP WO2019236954A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- formula
- moiety
- camptothecin
- covalent bond
- 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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- 102100024853 Carnitine O-palmitoyltransferase 2, mitochondrial Human genes 0.000 claims description 58
- 101000909313 Homo sapiens Carnitine O-palmitoyltransferase 2, mitochondrial Proteins 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 57
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical group O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 54
- 229910052757 nitrogen Inorganic materials 0.000 claims description 52
- 101000859570 Homo sapiens Carnitine O-palmitoyltransferase 1, liver isoform Proteins 0.000 claims description 50
- 101000989606 Homo sapiens Cholinephosphotransferase 1 Proteins 0.000 claims description 50
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 44
- KLWPJMFMVPTNCC-UHFFFAOYSA-N Camptothecin Natural products CCC1(O)C(=O)OCC2=C1C=C3C4Nc5ccccc5C=C4CN3C2=O KLWPJMFMVPTNCC-UHFFFAOYSA-N 0.000 claims description 40
- 229940127093 camptothecin Drugs 0.000 claims description 40
- VSJKWCGYPAHWDS-UHFFFAOYSA-N dl-camptothecin Natural products C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)C5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-UHFFFAOYSA-N 0.000 claims description 40
- VSJKWCGYPAHWDS-FQEVSTJZSA-N camptothecin Chemical compound C1=CC=C2C=C(CN3C4=CC5=C(C3=O)COC(=O)[C@]5(O)CC)C4=NC2=C1 VSJKWCGYPAHWDS-FQEVSTJZSA-N 0.000 claims description 38
- 101100497211 Solanum lycopersicum CPT6 gene Proteins 0.000 claims description 29
- 101100497209 Solanum lycopersicum CPT4 gene Proteins 0.000 claims description 25
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 101000896517 Homo sapiens Steroid 17-alpha-hydroxylase/17,20 lyase Proteins 0.000 claims description 20
- 102100021719 Steroid 17-alpha-hydroxylase/17,20 lyase Human genes 0.000 claims description 20
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 20
- 125000003277 amino group Chemical group 0.000 claims description 18
- 150000008134 glucuronides Chemical group 0.000 claims description 18
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 125000006850 spacer group Chemical group 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000001425 triazolyl group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 229960002317 succinimide Drugs 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 201000011510 cancer Diseases 0.000 claims description 9
- 150000002596 lactones Chemical group 0.000 claims description 9
- 239000003446 ligand Substances 0.000 claims description 9
- 206010025323 Lymphomas Diseases 0.000 claims description 8
- 101100497208 Solanum lycopersicum CPT3 gene Proteins 0.000 claims description 8
- 101100497210 Solanum lycopersicum CPT5 gene Proteins 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 208000032839 leukemia Diseases 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 125000004434 sulfur atom Chemical group 0.000 claims description 8
- 125000000524 functional group Chemical group 0.000 claims description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 6
- 230000001404 mediated effect Effects 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000001540 azides Chemical class 0.000 claims description 5
- 125000000686 lactone group Chemical group 0.000 claims description 5
- 239000002243 precursor Substances 0.000 claims description 5
- -1 caproyl-β-alanyl Chemical group 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 102000005744 Glycoside Hydrolases Human genes 0.000 claims description 2
- 108010031186 Glycoside Hydrolases Proteins 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 230000001143 conditioned effect Effects 0.000 claims description 2
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims description 2
- 229930182480 glucuronide Natural products 0.000 claims description 2
- 150000002402 hexoses Chemical class 0.000 claims description 2
- 150000002772 monosaccharides Chemical class 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 150000003573 thiols Chemical class 0.000 claims description 2
- 150000001345 alkine derivatives Chemical group 0.000 claims 2
- 108010044023 Ki-1 Antigen Proteins 0.000 claims 1
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- 150000001408 amides Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical group [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 8
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 8
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical group NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 6
- 108010077895 Sarcosine Proteins 0.000 description 4
- 150000001413 amino acids Chemical group 0.000 description 4
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 2
- GDFAOVXKHJXLEI-VKHMYHEASA-N N-methyl-L-alanine Chemical compound C[NH2+][C@@H](C)C([O-])=O GDFAOVXKHJXLEI-VKHMYHEASA-N 0.000 description 2
- AKCRVYNORCOYQT-YFKPBYRVSA-N N-methyl-L-valine Chemical compound CN[C@@H](C(C)C)C(O)=O AKCRVYNORCOYQT-YFKPBYRVSA-N 0.000 description 2
- VDIPNVCWMXZNFY-UHFFFAOYSA-N N-methyl-beta-alanine Chemical compound CNCCC(O)=O VDIPNVCWMXZNFY-UHFFFAOYSA-N 0.000 description 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 2
- 125000002355 alkine group Chemical group 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 description 2
- 125000006575 electron-withdrawing group Chemical group 0.000 description 2
- 229940043230 sarcosine Drugs 0.000 description 2
- 239000004474 valine Substances 0.000 description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 239000000427 antigen Substances 0.000 description 1
- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023205217A JP2024023543A (ja) | 2018-06-07 | 2023-12-05 | カンプトテシンコンジュゲート |
| JP2025070103A JP2025108689A (ja) | 2018-06-07 | 2025-04-22 | カンプトテシンコンジュゲート |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862681847P | 2018-06-07 | 2018-06-07 | |
| US62/681,847 | 2018-06-07 | ||
| US201862777491P | 2018-12-10 | 2018-12-10 | |
| US62/777,491 | 2018-12-10 | ||
| PCT/US2019/035971 WO2019236954A1 (en) | 2018-06-07 | 2019-06-07 | Camptothecin conjugates |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023205217A Division JP2024023543A (ja) | 2018-06-07 | 2023-12-05 | カンプトテシンコンジュゲート |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2021527040A JP2021527040A (ja) | 2021-10-11 |
| JPWO2019236954A5 true JPWO2019236954A5 (https=) | 2022-06-15 |
| JP2021527040A5 JP2021527040A5 (https=) | 2022-06-15 |
| JP7527978B2 JP7527978B2 (ja) | 2024-08-05 |
Family
ID=67139801
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2020567763A Active JP7527978B2 (ja) | 2018-06-07 | 2019-06-07 | カンプトテシンコンジュゲート |
| JP2023205217A Withdrawn JP2024023543A (ja) | 2018-06-07 | 2023-12-05 | カンプトテシンコンジュゲート |
| JP2025070103A Pending JP2025108689A (ja) | 2018-06-07 | 2025-04-22 | カンプトテシンコンジュゲート |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023205217A Withdrawn JP2024023543A (ja) | 2018-06-07 | 2023-12-05 | カンプトテシンコンジュゲート |
| JP2025070103A Pending JP2025108689A (ja) | 2018-06-07 | 2025-04-22 | カンプトテシンコンジュゲート |
Country Status (13)
| Country | Link |
|---|---|
| US (3) | US12194321B2 (https=) |
| EP (1) | EP3801633A1 (https=) |
| JP (3) | JP7527978B2 (https=) |
| KR (1) | KR20210053871A (https=) |
| CN (2) | CN112512592B (https=) |
| AU (1) | AU2019282767B2 (https=) |
| BR (1) | BR112020024915A2 (https=) |
| CA (1) | CA3101866A1 (https=) |
| IL (2) | IL278990B2 (https=) |
| MX (2) | MX2020013169A (https=) |
| SG (1) | SG11202011915TA (https=) |
| TW (1) | TWI851577B (https=) |
| WO (1) | WO2019236954A1 (https=) |
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CA3094313A1 (en) * | 2018-04-06 | 2019-10-10 | Seattle Genetics, Inc. | Camptothecin peptide conjugates |
| TWI851577B (zh) | 2018-06-07 | 2024-08-11 | 美商思進公司 | 喜樹鹼結合物 |
| CN114341162B (zh) | 2019-07-10 | 2025-10-17 | 赛博克萨2公司 | 作为治疗剂的细胞毒素的肽缀合物 |
| TW202116356A (zh) | 2019-07-10 | 2021-05-01 | 美商斯布雷克薩三號公司 | 作為治療劑之微管靶向藥劑之肽結合物 |
| CN112125915A (zh) * | 2019-09-18 | 2020-12-25 | 四川百利药业有限责任公司 | 一种喜树碱衍生物及其偶联物 |
| AU2020356955A1 (en) * | 2019-10-04 | 2022-04-14 | Seagen Inc. | Camptothecin peptide conjugates |
| WO2021067820A1 (en) * | 2019-10-04 | 2021-04-08 | Seagen Inc. | Formulation of antibody-drug conjugate |
| AU2021213421B2 (en) | 2020-01-31 | 2025-02-06 | Innate Pharma | Treatment of cancer |
| CA3183602A1 (en) * | 2020-05-13 | 2021-11-18 | Seagen Inc. | Methods of treating cancer using a combination of anti-cd30 antibody-drug conjugates |
| KR102349925B1 (ko) * | 2020-07-16 | 2022-01-12 | 주식회사 피노바이오 | Fl118 약물을 포함하는 화합물 및 이를 이용한 면역접합체 |
| AU2022207454A1 (en) * | 2021-01-15 | 2023-06-22 | R.P. Scherer Technologies, Llc | Camptothecine antibody-drug conjugates and methods of use thereof |
| WO2022155362A1 (en) * | 2021-01-15 | 2022-07-21 | R.P. Scherer Technologies, Llc | Dual-cleavage ester linkers for antibody-drug conjugates |
| KR20250120438A (ko) * | 2021-02-05 | 2025-08-08 | 쓰촨 케룬-바이오테크 바이오파마수티컬 컴퍼니 리미티드 | 캄프토테신 화합물, 그의 제조방법 및 그의 응용 |
| MX2023008895A (es) * | 2021-02-09 | 2023-08-09 | Medilink Therapeutics Suzhou Co Ltd | Conjugado de sustancia bioactiva, metodo de preparacion y uso del mismo. |
| US12521444B2 (en) | 2021-02-25 | 2026-01-13 | Fortvita Biologics Limited | Anti-HER2 antibody-drug conjugates and uses thereof |
| CN117015545A (zh) * | 2021-03-12 | 2023-11-07 | 国立研究开发法人科学技术振兴机构 | Sn-38衍生物、包含该衍生物的纳米粒子、医药及该纳米粒子的制造方法 |
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| EP4496593A1 (en) | 2022-03-23 | 2025-01-29 | Synaffix B.V. | Antibody-conjugates for targeting of tumours expressing nectin-4 |
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| KR20250009592A (ko) | 2022-04-12 | 2025-01-17 | 미네르바 바이오테크놀로지 코포레이션 | 항-가변 muc1* 항체 및 그의 용도 |
| KR20230149752A (ko) * | 2022-04-20 | 2023-10-27 | 주식회사 피노바이오 | Ddx5 단백질에 결합하는 캄토테신 유도체 및 이의 프로드럭 |
| WO2023217227A1 (zh) * | 2022-05-12 | 2023-11-16 | 先声再明医药有限公司 | 喜树碱类衍生物及配体-药物偶联物 |
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| WO2024212922A1 (zh) * | 2023-04-11 | 2024-10-17 | 映恩生物制药（苏州）有限公司 | 喜树碱类化合物及其偶联物、其制备方法和用途 |
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| CN119424671A (zh) * | 2023-08-01 | 2025-02-14 | 上海新理念生物医药科技有限公司 | 含糖基吡啶型连接子的抗体药物偶联物 |
| WO2025078841A2 (en) | 2023-10-11 | 2025-04-17 | Antikor Biopharma Limited | Antibodies, conjugates, and uses thereof |
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| WO2025149947A1 (en) | 2024-01-12 | 2025-07-17 | Seagen Inc. | Antibody-drug conjugates |
| WO2025169056A1 (en) | 2024-02-06 | 2025-08-14 | Seagen Inc. | Methods of treating cancers using anti-cd30 antibody-drug conjugates |
| TW202602929A (zh) | 2024-03-21 | 2026-01-16 | 美商思進公司 | Ｃｄ２５抗體、抗體-藥物共軛體及彼等之用途 |
| WO2025223507A1 (zh) * | 2024-04-25 | 2025-10-30 | 江苏康宁杰瑞生物制药有限公司 | 化合物及其偶联物 |
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| TW202435917A (zh) | 2022-11-17 | 2024-09-16 | 美商西雅圖遺傳學公司 | Ceacam5抗體-藥物接合物及其使用方法 |
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2019
- 2019-06-06 TW TW108119649A patent/TWI851577B/zh active
- 2019-06-07 SG SG11202011915TA patent/SG11202011915TA/en unknown
- 2019-06-07 BR BR112020024915-7A patent/BR112020024915A2/pt unknown
- 2019-06-07 US US16/972,469 patent/US12194321B2/en active Active
- 2019-06-07 JP JP2020567763A patent/JP7527978B2/ja active Active
- 2019-06-07 CN CN201980050566.6A patent/CN112512592B/zh active Active
- 2019-06-07 MX MX2020013169A patent/MX2020013169A/es unknown
- 2019-06-07 CA CA3101866A patent/CA3101866A1/en active Pending
- 2019-06-07 AU AU2019282767A patent/AU2019282767B2/en active Active
- 2019-06-07 IL IL278990A patent/IL278990B2/en unknown
- 2019-06-07 KR KR1020217000418A patent/KR20210053871A/ko not_active Ceased
- 2019-06-07 CN CN202511210624.0A patent/CN121059827A/zh active Pending
- 2019-06-07 EP EP19735436.8A patent/EP3801633A1/en active Pending
- 2019-06-07 WO PCT/US2019/035971 patent/WO2019236954A1/en not_active Ceased
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2020
- 2020-12-03 MX MX2024008677A patent/MX2024008677A/es unknown
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2023
- 2023-12-05 JP JP2023205217A patent/JP2024023543A/ja not_active Withdrawn
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2024
- 2024-03-12 IL IL311437A patent/IL311437B1/en unknown
- 2024-11-08 US US18/942,261 patent/US20250073348A1/en active Pending
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2025
- 2025-03-24 US US19/088,772 patent/US20250248994A1/en active Pending
- 2025-04-22 JP JP2025070103A patent/JP2025108689A/ja active Pending
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