JP2018503639A5 - - Google Patents
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- JP2018503639A5 JP2018503639A5 JP2017537227A JP2017537227A JP2018503639A5 JP 2018503639 A5 JP2018503639 A5 JP 2018503639A5 JP 2017537227 A JP2017537227 A JP 2017537227A JP 2017537227 A JP2017537227 A JP 2017537227A JP 2018503639 A5 JP2018503639 A5 JP 2018503639A5
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- JP
- Japan
- Prior art keywords
- alkyl
- independently
- formula
- unsubstituted
- 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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- 125000000217 alkyl group Chemical group 0.000 claims 48
- 229910052739 hydrogen Inorganic materials 0.000 claims 18
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 12
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 9
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1H-1,2-benzodiazepine Chemical class N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 claims 8
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000002947 alkylene group Chemical group 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 4
- 102000004965 antibodies Human genes 0.000 claims 4
- 108090001123 antibodies Proteins 0.000 claims 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 4
- UCMIRNVEIXFBKS-UHFFFAOYSA-N β-Alanine Chemical compound NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 claims 4
- 241000257303 Hymenoptera Species 0.000 claims 3
- 125000005418 aryl aryl group Chemical group 0.000 claims 3
- 125000004350 aryl cycloalkyl group Chemical group 0.000 claims 3
- 125000000732 arylene group Chemical group 0.000 claims 3
- 125000006448 cycloalkyl cycloalkyl group Chemical group 0.000 claims 3
- 125000002993 cycloalkylene group Chemical group 0.000 claims 3
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 3
- 125000005349 heteroarylcycloalkyl group Chemical group 0.000 claims 3
- 125000005549 heteroarylene group Chemical group 0.000 claims 3
- 125000006588 heterocycloalkylene group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 229960003767 Alanine Drugs 0.000 claims 2
- 239000004475 Arginine Substances 0.000 claims 2
- 229960001230 Asparagine Drugs 0.000 claims 2
- 229960005261 Aspartic Acid Drugs 0.000 claims 2
- MTCFGRXMJLQNBG-UWTATZPHSA-N D-serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 claims 2
- QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical compound C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 claims 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N GABA Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 claims 2
- 229960002989 Glutamic Acid Drugs 0.000 claims 2
- 239000004471 Glycine Substances 0.000 claims 2
- 229960000310 ISOLEUCINE Drugs 0.000 claims 2
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-2-aminohexanoic acid zwitterion Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 claims 2
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid zwitterion Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-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
- 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
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline zwitterion Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 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
- 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
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-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
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-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
- 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
- 239000004472 Lysine Substances 0.000 claims 2
- 229960003104 Ornithine Drugs 0.000 claims 2
- 229960005190 Phenylalanine Drugs 0.000 claims 2
- 239000004473 Threonine Substances 0.000 claims 2
- 235000004279 alanine Nutrition 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 229960003692 aminobutyric acid Drugs 0.000 claims 2
- 229960003121 arginine Drugs 0.000 claims 2
- 235000009697 arginine Nutrition 0.000 claims 2
- 235000009582 asparagine Nutrition 0.000 claims 2
- 235000003704 aspartic acid Nutrition 0.000 claims 2
- 229940000635 beta-Alanine Drugs 0.000 claims 2
- 201000011510 cancer Diseases 0.000 claims 2
- 229960002173 citrulline Drugs 0.000 claims 2
- 235000013477 citrulline Nutrition 0.000 claims 2
- 235000018417 cysteine Nutrition 0.000 claims 2
- 229940013945 gamma-Aminobutyric Acid Drugs 0.000 claims 2
- 235000013922 glutamic acid Nutrition 0.000 claims 2
- 239000004220 glutamic acid Substances 0.000 claims 2
- 235000004554 glutamine Nutrition 0.000 claims 2
- 239000004474 valine Substances 0.000 claims 2
- UHBYWPGGCSDKFX-VKHMYHEASA-N γ-carboxy-L-glutamic acid zwitterion Chemical compound OC(=O)[C@@H](N)CC(C(O)=O)C(O)=O UHBYWPGGCSDKFX-VKHMYHEASA-N 0.000 claims 2
- 206010017758 Gastric cancer Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 206010033128 Ovarian cancer Diseases 0.000 claims 1
- 206010038389 Renal cancer Diseases 0.000 claims 1
- 201000010982 kidney cancer Diseases 0.000 claims 1
- 201000007270 liver cancer Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 239000000546 pharmaceutic aid Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- 201000011549 stomach cancer Diseases 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562103157P | 2015-01-14 | 2015-01-14 | |
| US62/103,157 | 2015-01-14 | ||
| US201562215928P | 2015-09-09 | 2015-09-09 | |
| US62/215,928 | 2015-09-09 | ||
| PCT/US2016/013136 WO2016115191A1 (en) | 2015-01-14 | 2016-01-13 | Benzodiazepine dimers, conjugates thereof, and methods of making and using |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018503639A JP2018503639A (ja) | 2018-02-08 |
| JP2018503639A5 true JP2018503639A5 (US20040106767A1-20040603-C00005.png) | 2018-04-12 |
| JP6498773B2 JP6498773B2 (ja) | 2019-04-10 |
Family
ID=55305072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017537227A Active JP6498773B2 (ja) | 2015-01-14 | 2016-01-13 | ベンゾジアゼピン二量体、そのコンジュゲート、ならびに製造および使用方法 |
Country Status (19)
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP6676058B2 (ja) * | 2015-01-14 | 2020-04-08 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | ヘテロアリーレン架橋したベンゾジアゼピン二量体、そのコンジュゲート、ならびに製造および使用方法 |
| US9504694B2 (en) * | 2015-03-19 | 2016-11-29 | Cellerant Therapeutics, Inc. | Isoquinolidinobenzodiazepines |
| US20190218294A1 (en) | 2016-09-09 | 2019-07-18 | Bristol-Myers Squibb Company | Use of an anti-pd-1 antibody in combination with an anti-mesothelin antibody in cancer treatment |
| WO2018053552A2 (en) * | 2016-09-19 | 2018-03-22 | Cellerant Therapeutics, Inc. | Isoquinolidinobenzodiazepines |
| JP2019530707A (ja) * | 2016-10-10 | 2019-10-24 | セレラント セラピューティクス インコーポレイテッド | イソキノリジノベンゾジアゼピン（ｉｑｂ）−１（クロロメチル）−２，３−ジヒドロ−１ｈ−ベンゾ［ｅ］インドール（ｃｂｉ）二量体 |
| US10738338B2 (en) | 2016-10-18 | 2020-08-11 | The Research Foundation for the State University | Method and composition for biocatalytic protein-oligonucleotide conjugation and protein-oligonucleotide conjugate |
| WO2018075842A1 (en) | 2016-10-20 | 2018-04-26 | Bristol-Myers Squibb Company | Condensed benzodiazepine derivatives and conjugates made therefrom |
| SG11201906666QA (en) * | 2017-01-25 | 2019-08-27 | Immunogen Inc | Methods of preparing cytotoxic benzodiazepine derivatives |
| WO2018195243A1 (en) * | 2017-04-20 | 2018-10-25 | Immunogen, Inc. | Cytotoxic benzodiazepine derivatives and conjugates thereof |
| EP3668545A2 (en) | 2017-08-16 | 2020-06-24 | Bristol-Myers Squibb Company | Prodruggable antibodies, prodrugs thereof, and methods of use and making |
| GB201714115D0 (en) | 2017-09-04 | 2017-10-18 | Femtogenix Ltd | Cytotoxic agents |
| IL301637B2 (en) | 2017-09-29 | 2024-10-01 | Daiichi Sankyo Co Ltd | Conjugation of an antibody with a pyrrolobenzodiazepine derivative |
| WO2019229536A2 (en) | 2018-05-29 | 2019-12-05 | Intocell, Inc. | Novel benzodiazepine derivatives and uses thereof |
| US20220009946A1 (en) * | 2018-10-31 | 2022-01-13 | Intocell, Inc. | Fused heterocyclic benzodiazepine derivatives and uses thereof |
| AU2019379418A1 (en) | 2018-11-14 | 2021-06-03 | Daiichi Sankyo Company, Limited | Anti-CDH6 antibody-pyrrolobenzodiazepine derivative conjugate |
| WO2020112588A1 (en) | 2018-11-30 | 2020-06-04 | Bristol-Myers Squibb Company | Antibody comprising a glutamine-containing light chain c-terminal extension, conjugates thereof, and methods and uses |
| KR20210102334A (ko) | 2018-12-12 | 2021-08-19 | 브리스톨-마이어스 스큅 컴퍼니 | 트랜스글루타미나제 접합을 위해 변형된 항체, 그의 접합체, 및 방법 및 용도 |
| GB201901197D0 (en) | 2019-01-29 | 2019-03-20 | Femtogenix Ltd | G-A Crosslinking cytotoxic agents |
| BR112021017616A2 (pt) | 2019-03-25 | 2021-11-09 | Daiichi Sankyo Co Ltd | Conjugado de derivado de anticorpo anti-her2-pirrolobenzodiazepina |
| WO2020196474A1 (ja) | 2019-03-25 | 2020-10-01 | 第一三共株式会社 | 抗体－ピロロベンゾジアゼピン誘導体コンジュゲート |
| TWI841715B (zh) | 2019-03-27 | 2024-05-11 | 日商第一三共股份有限公司 | 抗體-吡咯并苯二氮呯衍生物結合物及ｐａｒｐ抑制劑之組合及其用途 |
| US20220251206A1 (en) | 2019-06-11 | 2022-08-11 | Bristol-Myers Squibb Company | Anti-ctla4 antibody prodruggable (probody) at a cdr position |
| WO2021055306A1 (en) | 2019-09-16 | 2021-03-25 | Bristol-Myers Squibb Company | Dual capture method for analysis of antibody-drug conjugates |
| AU2022207708A1 (en) | 2021-01-13 | 2023-07-27 | Daiichi Sankyo Company, Limited | Antibody-pyrrolobenzodiazepine derivative conjugate |
| CN113372245B (zh) * | 2021-06-17 | 2023-01-13 | 仪征市海帆化工有限公司 | 一种n-苯甲酰基-o,o-对甲苯磺酰基-二乙醇胺的合成方法 |
| WO2023037237A1 (en) * | 2021-09-09 | 2023-03-16 | Wavelength Enterprises Ltd | Process for the preparation of remimazolam |
| AU2022357933A1 (en) * | 2021-09-30 | 2024-04-11 | Ajinomoto Co., Inc. | Conjugate of antibody and functional substance or salt thereof, and antibody derivative and compound or salts thereof to be used in producing conjugate or salt thereof |
| EP4442828A1 (en) | 2021-11-30 | 2024-10-09 | Daiichi Sankyo Company, Limited | Protease-cleavable masked antibodies |
| AU2023218678A1 (en) | 2022-02-09 | 2024-08-01 | Daiichi Sankyo Company, Limited | Environmentally responsive masked antibody and use thereof |
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-
2016
- 2016-01-13 CA CA2973354A patent/CA2973354A1/en not_active Abandoned
- 2016-01-13 CN CN201680006151.5A patent/CN107428780B/zh active Active
- 2016-01-13 JP JP2017537227A patent/JP6498773B2/ja active Active
- 2016-01-13 US US14/994,296 patent/US9527871B2/en active Active
- 2016-01-13 MX MX2017009145A patent/MX2017009145A/es unknown
- 2016-01-13 SG SG11201705646XA patent/SG11201705646XA/en unknown
- 2016-01-13 EA EA201791550A patent/EA201791550A1/ru unknown
- 2016-01-13 TW TW105100987A patent/TW201632531A/zh unknown
- 2016-01-13 EP EP16703196.2A patent/EP3245213B1/en active Active
- 2016-01-13 WO PCT/US2016/013136 patent/WO2016115191A1/en active Application Filing
- 2016-01-13 ES ES16703196T patent/ES2783624T3/es active Active
- 2016-01-13 BR BR112017014599A patent/BR112017014599A2/pt not_active Application Discontinuation
- 2016-01-13 PE PE2017001216A patent/PE20171184A1/es unknown
- 2016-01-13 KR KR1020177022244A patent/KR20170102980A/ko not_active Application Discontinuation
- 2016-01-13 AU AU2016206798A patent/AU2016206798A1/en not_active Abandoned
- 2016-11-15 US US15/351,843 patent/US9676794B2/en active Active
-
2017
- 2017-05-05 US US15/587,715 patent/US9822144B2/en active Active
- 2017-07-10 IL IL253402A patent/IL253402A0/en unknown
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- 2017-08-10 CO CONC2017/0008078A patent/CO2017008078A2/es unknown
- 2017-10-17 US US15/785,675 patent/US10112975B2/en active Active
