JP2020512270A5 - - Google Patents
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- Publication number
- JP2020512270A5 JP2020512270A5 JP2019515212A JP2019515212A JP2020512270A5 JP 2020512270 A5 JP2020512270 A5 JP 2020512270A5 JP 2019515212 A JP2019515212 A JP 2019515212A JP 2019515212 A JP2019515212 A JP 2019515212A JP 2020512270 A5 JP2020512270 A5 JP 2020512270A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- alkenyl
- aryl
- 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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- 125000000217 alkyl group Chemical group 0.000 claims description 89
- 125000003118 aryl group Chemical group 0.000 claims description 84
- 125000001072 heteroaryl group Chemical group 0.000 claims description 73
- 239000000539 dimer Substances 0.000 claims description 55
- 125000003545 alkoxy group Chemical group 0.000 claims description 50
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 49
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 32
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 30
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 29
- 239000003446 ligand Substances 0.000 claims description 27
- 239000000651 prodrug Substances 0.000 claims description 27
- 229940002612 prodrug Drugs 0.000 claims description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
- 206010028980 Neoplasm Diseases 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 102000004357 Transferases Human genes 0.000 claims description 10
- 108090000992 Transferases Proteins 0.000 claims description 10
- 150000001413 amino acids Chemical class 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 230000002062 proliferating effect Effects 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 235000001014 amino acid Nutrition 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- -1 methoxy, ethoxy Chemical group 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 201000011510 cancer Diseases 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 235000018102 proteins Nutrition 0.000 claims description 5
- 102000004169 proteins and genes Human genes 0.000 claims description 5
- 108090000623 proteins and genes Proteins 0.000 claims description 5
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
- 125000000739 C2-C30 alkenyl group Chemical group 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 206010039491 Sarcoma Diseases 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 150000008195 galaktosides Chemical group 0.000 claims description 4
- 150000008134 glucuronides Chemical group 0.000 claims description 4
- 150000002430 hydrocarbons Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 238000011282 treatment Methods 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 208000020084 Bone disease Diseases 0.000 claims description 2
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 2
- 206010006187 Breast cancer Diseases 0.000 claims description 2
- 208000026310 Breast neoplasm Diseases 0.000 claims description 2
- 206010009944 Colon cancer Diseases 0.000 claims description 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 2
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 2
- 206010033128 Ovarian cancer Diseases 0.000 claims description 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 2
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 2
- 206010060862 Prostate cancer Diseases 0.000 claims description 2
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 2
- 201000004681 Psoriasis Diseases 0.000 claims description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- 208000015634 Rectal Neoplasms Diseases 0.000 claims description 2
- 206010038389 Renal cancer Diseases 0.000 claims description 2
- 206010041067 Small cell lung cancer Diseases 0.000 claims description 2
- 208000024313 Testicular Neoplasms Diseases 0.000 claims description 2
- 206010057644 Testis cancer Diseases 0.000 claims description 2
- 239000000427 antigen Substances 0.000 claims description 2
- 102000036639 antigens Human genes 0.000 claims description 2
- 108091007433 antigens Proteins 0.000 claims description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 2
- 235000018417 cysteine Nutrition 0.000 claims description 2
- 125000004030 farnesyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000002686 geranylgeranyl group Chemical group [H]C([*])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])/C([H])=C(C([H])([H])[H])/C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 201000010982 kidney cancer Diseases 0.000 claims description 2
- 208000032839 leukemia Diseases 0.000 claims description 2
- 201000007270 liver cancer Diseases 0.000 claims description 2
- 208000014018 liver neoplasm Diseases 0.000 claims description 2
- 201000005202 lung cancer Diseases 0.000 claims description 2
- 208000020816 lung neoplasm Diseases 0.000 claims description 2
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 2
- 201000001441 melanoma Diseases 0.000 claims description 2
- 210000004798 organs belonging to the digestive system Anatomy 0.000 claims description 2
- 201000008968 osteosarcoma Diseases 0.000 claims description 2
- 201000002528 pancreatic cancer Diseases 0.000 claims description 2
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 206010038038 rectal cancer Diseases 0.000 claims description 2
- 201000001275 rectum cancer Diseases 0.000 claims description 2
- 208000000587 small cell lung carcinoma Diseases 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims description 2
- 201000003120 testicular cancer Diseases 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 2
- 206010005003 Bladder cancer Diseases 0.000 claims 1
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 1
- 150000001345 alkine derivatives Chemical class 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- 201000005112 urinary bladder cancer Diseases 0.000 claims 1
- 239000012453 solvate Substances 0.000 description 26
- 0 CSC(*(*)CN)C(C[C@](C1*)N)C1C=O Chemical compound CSC(*(*)CN)C(C[C@](C1*)N)C1C=O 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 208000035269 cancer or benign tumor Diseases 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023081396A JP2023113699A (ja) | 2017-03-29 | 2023-05-17 | ピロロベンゾジアゼピン二量体前駆体及びそのリガンド－リンカーコンジュゲート化合物 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR10-2017-0039841 | 2017-03-29 | ||
| KR20170039841 | 2017-03-29 | ||
| KR10-2018-0036895 | 2018-03-29 | ||
| PCT/KR2018/003744 WO2018182341A1 (ko) | 2017-03-29 | 2018-03-29 | 피롤로벤조디아제핀 이량체 전구체 및 이의 리간드-링커 접합체 화합물 |
| KR1020180036895A KR101938800B1 (ko) | 2017-03-29 | 2018-03-29 | 피롤로벤조디아제핀 이량체 전구체 및 이의 리간드-링커 접합체 화합물 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023081396A Division JP2023113699A (ja) | 2017-03-29 | 2023-05-17 | ピロロベンゾジアゼピン二量体前駆体及びそのリガンド－リンカーコンジュゲート化合物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2020512270A JP2020512270A (ja) | 2020-04-23 |
| JP2020512270A5 true JP2020512270A5 (enExample) | 2021-05-13 |
| JP7664680B2 JP7664680B2 (ja) | 2025-04-18 |
Family
ID=63876096
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019515212A Active JP7664680B2 (ja) | 2017-03-29 | 2018-03-29 | ピロロベンゾジアゼピン二量体前駆体及びそのリガンド－リンカーコンジュゲート化合物 |
| JP2023081396A Pending JP2023113699A (ja) | 2017-03-29 | 2023-05-17 | ピロロベンゾジアゼピン二量体前駆体及びそのリガンド－リンカーコンジュゲート化合物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023081396A Pending JP2023113699A (ja) | 2017-03-29 | 2023-05-17 | ピロロベンゾジアゼピン二量体前駆体及びそのリガンド－リンカーコンジュゲート化合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US11654197B2 (enExample) |
| EP (1) | EP3604311A4 (enExample) |
| JP (2) | JP7664680B2 (enExample) |
| KR (4) | KR101938800B1 (enExample) |
| CN (1) | CN109790171B (enExample) |
| AU (1) | AU2018246806B2 (enExample) |
| CA (1) | CA3058360A1 (enExample) |
| IL (1) | IL269535B2 (enExample) |
| MX (1) | MX2019011655A (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2017089894A1 (en) | 2015-11-25 | 2017-06-01 | Legochem Biosciences, Inc. | Conjugates comprising peptide groups and methods related thereto |
| CA3006249A1 (en) | 2015-11-25 | 2017-06-01 | Legochem Biosciences, Inc. | Antibody-drug conjugates comprising branched linkers and methods related thereto |
| HRP20240795T1 (hr) | 2015-11-25 | 2024-09-13 | Ligachem Biosciences Inc. | Konjugati koji se sastoje od samozapaljujućih skupina i postupci povezani s njima |
| IL269535B2 (en) | 2017-03-29 | 2024-11-01 | Ligachem Biosciences Inc | Pyrrolobenzodiazepine dimer prodrug and ligand-linker conjugate compound of the same |
| GB201803342D0 (en) * | 2018-03-01 | 2018-04-18 | Medimmune Ltd | Methods |
| EP3790591A4 (en) | 2018-05-09 | 2022-05-11 | LegoChem Biosciences, Inc. | Compositions and methods related to anti-cd19 antibody drug conjugates |
| WO2020141923A2 (ko) | 2019-01-03 | 2020-07-09 | 주식회사 레고켐 바이오사이언스 | 안전성이 향상된 피롤로벤조디아제핀 이량체 화합물 및 이의 용도 |
| KR20200084802A (ko) | 2019-01-03 | 2020-07-13 | 주식회사 레고켐 바이오사이언스 | 안전성이 향상된 피롤로벤조디아제핀 이량체 화합물 및 이의 용도 |
| BR112021017303A2 (pt) | 2019-03-06 | 2021-11-16 | Legochem Biosciences Inc | Conjugado de anticorpo ou um sal ou solvato farmaceuticamente aceitável deste, anticorpo que se liga com especificidade ao dlk1 ou um fragmento de ligação ao antígeno deste, composição farmacêutica para prevenção ou tratamento de doença proliferativa, câncer ou angiogênica, métodos para prevenção e para tratamento de doença proliferativa, câncer ou angiogênica, e, uso do conjugado |
| KR20210028544A (ko) * | 2019-09-04 | 2021-03-12 | 주식회사 레고켐 바이오사이언스 | 인간 ror1에 대한 항체를 포함하는 항체 약물 접합체 및 이의 용도 |
| WO2021137646A1 (ko) | 2019-12-31 | 2021-07-08 | 주식회사 레고켐바이오사이언스 | 피롤로벤조디아제핀 유도체 및 이의 리간드-링커 접합체 |
| WO2022211508A1 (ko) | 2021-03-30 | 2022-10-06 | 주식회사 레고켐바이오사이언스 | 인간 cldn18.2에 대한 항체를 포함하는 항체 약물 접합체 및 이의 용도 |
| GB202203070D0 (en) * | 2022-03-04 | 2022-04-20 | Iksuda Therapeutics Ltd | Anti-canag antibody conjugate |
| CN115429890B (zh) * | 2022-08-04 | 2024-05-24 | 辽宁键凯科技有限公司 | 一种缀合物及用其制备的抗体药物偶联物 |
| CN115772163B (zh) * | 2022-12-09 | 2025-07-22 | 中国科学院成都生物研究所 | 吲哚糖苷类化合物及吡咯糖苷类化合物及合成方法与应用 |
| EP4389152A1 (en) | 2022-12-23 | 2024-06-26 | Synaffix B.V. | Conjugates of pbd prodrugs |
| CN120857932A (zh) * | 2023-02-22 | 2025-10-28 | 坚毅科学股份有限公司 | 用于靶向肿瘤相关巨噬细胞的组合物和方法 |
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-
2018
- 2018-03-29 IL IL269535A patent/IL269535B2/en unknown
- 2018-03-29 US US16/328,256 patent/US11654197B2/en active Active
- 2018-03-29 CN CN201880003365.6A patent/CN109790171B/zh active Active
- 2018-03-29 CA CA3058360A patent/CA3058360A1/en active Pending
- 2018-03-29 KR KR1020180036895A patent/KR101938800B1/ko active Active
- 2018-03-29 EP EP18774896.7A patent/EP3604311A4/en active Pending
- 2018-03-29 MX MX2019011655A patent/MX2019011655A/es unknown
- 2018-03-29 AU AU2018246806A patent/AU2018246806B2/en active Active
- 2018-03-29 JP JP2019515212A patent/JP7664680B2/ja active Active
- 2018-08-08 KR KR1020180092623A patent/KR20180110649A/ko not_active Ceased
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2021
- 2021-05-14 KR KR1020210063019A patent/KR20210058795A/ko not_active Ceased
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2022
- 2022-01-10 KR KR1020220003168A patent/KR102489250B1/ko active Active
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2023
- 2023-02-24 US US18/113,948 patent/US12398124B2/en active Active
- 2023-05-17 JP JP2023081396A patent/JP2023113699A/ja active Pending
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