JP2020512270A5 - - Google Patents
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- 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 | ||
| KR1020180036895A KR101938800B1 (ko) | 2017-03-29 | 2018-03-29 | 피롤로벤조디아제핀 이량체 전구체 및 이의 리간드-링커 접합체 화합물 |
| PCT/KR2018/003744 WO2018182341A1 (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 (https=) | 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 (https=) |
| EP (1) | EP3604311A4 (https=) |
| JP (2) | JP7664680B2 (https=) |
| KR (4) | KR101938800B1 (https=) |
| CN (1) | CN109790171B (https=) |
| AU (1) | AU2018246806B2 (https=) |
| CA (1) | CA3058360A1 (https=) |
| IL (1) | IL269535B2 (https=) |
| MX (1) | MX2019011655A (https=) |
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| AU2016359235B2 (en) | 2015-11-25 | 2022-09-15 | Ligachem Biosciences Inc. | Antibody-drug conjugates comprising branched linkers and methods related thereto |
| KR102847348B1 (ko) | 2015-11-25 | 2025-08-19 | 주식회사 리가켐바이오사이언스 | 펩타이드 그룹을 포함하는 접합체 및 이와 관련된 제조방법 |
| CA3058360A1 (en) | 2017-03-29 | 2018-10-04 | Legochem Biosciences, Inc. | Pyrrolobenzodiazepine dimer prodrug and ligand-linker conjugate compound of the same |
| GB201803342D0 (en) * | 2018-03-01 | 2018-04-18 | Medimmune Ltd | Methods |
| CN112601555A (zh) | 2018-05-09 | 2021-04-02 | 乐高化学生物科学股份有限公司 | 与抗cd19抗体药物结合物相关的组合物和方法 |
| KR20200084802A (ko) | 2019-01-03 | 2020-07-13 | 주식회사 레고켐 바이오사이언스 | 안전성이 향상된 피롤로벤조디아제핀 이량체 화합물 및 이의 용도 |
| WO2020141923A2 (ko) | 2019-01-03 | 2020-07-09 | 주식회사 레고켐 바이오사이언스 | 안전성이 향상된 피롤로벤조디아제핀 이량체 화합물 및 이의 용도 |
| EP3936150A4 (en) | 2019-03-06 | 2023-03-29 | LegoChem Biosciences, Inc. | ANTIBODY-DRUG CONJUGATES COMPRISING ANTIBODY AGAINST HUMAN DLK1 AND USE THEREOF |
| KR20210028544A (ko) * | 2019-09-04 | 2021-03-12 | 주식회사 레고켐 바이오사이언스 | 인간 ror1에 대한 항체를 포함하는 항체 약물 접합체 및 이의 용도 |
| KR20210086557A (ko) | 2019-12-31 | 2021-07-08 | 주식회사 레고켐 바이오사이언스 | 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 |
| CN119798218A (zh) * | 2024-12-31 | 2025-04-11 | 南京优氟医药科技有限公司 | 一种e3酶配体-连接链复合物及其制备方法 |
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2018
- 2018-03-29 CA CA3058360A patent/CA3058360A1/en active Pending
- 2018-03-29 US US16/328,256 patent/US11654197B2/en active Active
- 2018-03-29 IL IL269535A patent/IL269535B2/en unknown
- 2018-03-29 KR KR1020180036895A patent/KR101938800B1/ko active Active
- 2018-03-29 JP JP2019515212A patent/JP7664680B2/ja active Active
- 2018-03-29 EP EP18774896.7A patent/EP3604311A4/en active Pending
- 2018-03-29 AU AU2018246806A patent/AU2018246806B2/en active Active
- 2018-03-29 CN CN201880003365.6A patent/CN109790171B/zh active Active
- 2018-03-29 MX MX2019011655A patent/MX2019011655A/es unknown
- 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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