JP2018526340A5 - - Google Patents
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- JP2018526340A5 JP2018526340A5 JP2018502791A JP2018502791A JP2018526340A5 JP 2018526340 A5 JP2018526340 A5 JP 2018526340A5 JP 2018502791 A JP2018502791 A JP 2018502791A JP 2018502791 A JP2018502791 A JP 2018502791A JP 2018526340 A5 JP2018526340 A5 JP 2018526340A5
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- 150000001875 compounds Chemical class 0.000 claims 39
- 150000003839 salts Chemical class 0.000 claims 17
- 239000011780 sodium chloride Substances 0.000 claims 17
- 239000000178 monomer Substances 0.000 claims 10
- 125000006242 amine protecting group Chemical group 0.000 claims 6
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 5
- FAMRKDQNMBBFBR-BQYQJAHWSA-N Diethyl azodicarboxylate Chemical group CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims 4
- 239000003153 chemical reaction reagent Substances 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- 125000006241 alcohol protecting group Chemical group 0.000 claims 3
- BZKBCQXYZZXSCO-UHFFFAOYSA-N sodium hydride Chemical compound [H-].[Na+] BZKBCQXYZZXSCO-UHFFFAOYSA-N 0.000 claims 3
- USVVENVKYJZFMW-UHFFFAOYSA-L N-carboxylatoiminocarbamate Chemical compound [O-]C(=O)N=NC([O-])=O USVVENVKYJZFMW-UHFFFAOYSA-L 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N Triphenylphosphine Chemical group C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (NE)-N-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 claims 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L Caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims 1
- OQJBFFCUFALWQL-UHFFFAOYSA-N N-(piperidine-1-carbonylimino)piperidine-1-carboxamide Chemical compound C1CCCCN1C(=O)N=NC(=O)N1CCCCC1 OQJBFFCUFALWQL-UHFFFAOYSA-N 0.000 claims 1
- 230000003213 activating Effects 0.000 claims 1
- 239000012190 activator Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 239000012320 chlorinating reagent Substances 0.000 claims 1
- 150000002466 imines Chemical class 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- 239000001184 potassium carbonate Substances 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- OCFVSFVLVRNXFJ-UHFFFAOYSA-N potassium hydride Inorganic materials [H-].[K+] OCFVSFVLVRNXFJ-UHFFFAOYSA-N 0.000 claims 1
- 239000003638 reducing agent Substances 0.000 claims 1
- 239000001187 sodium carbonate Substances 0.000 claims 1
- 229910000029 sodium carbonate Inorganic materials 0.000 claims 1
- QKSQWQOAUQFORH-UHFFFAOYSA-N tert-butyl N-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C QKSQWQOAUQFORH-UHFFFAOYSA-N 0.000 claims 1
- 0 C[C@@](C(N[C@@](C)C(Nc1cc(C*)cc(CO)c1)=O)=O)NC(CCCCC(*)=O)=O Chemical compound C[C@@](C(N[C@@](C)C(Nc1cc(C*)cc(CO)c1)=O)=O)NC(CCCCC(*)=O)=O 0.000 description 2
- ROVBYDCETXMZLN-UHFFFAOYSA-N COc(cc(c(N=CC1N2c3ccccc3C1)c1)C2=O)c1O Chemical compound COc(cc(c(N=CC1N2c3ccccc3C1)c1)C2=O)c1O ROVBYDCETXMZLN-UHFFFAOYSA-N 0.000 description 1
Claims (16)
- アルコール活性化剤およびアゾジカルボキシレートの存在下において前記式(14d)の化合物を式(d1)のモノマーと反応させる、請求項1に記載の方法。
- 前記アルコール活性化剤がトリフェニルホスフィンである、請求項2に記載の方法。
- 前記アゾジカルボキシレートが、ジエチルアゾジカルボキシレート(DEAD)、ジイソプロピルアゾジカルボキシレート(DIAD)、1,1'−(アゾジカルボニル)ジピペリジン(ADDP)、及びジtert−ブチルアゾジカルボキシレート(DTAD)からなる群から選択される、請求項2または3に記載の方法。
- 塩基の存在下において前記式(17d)の化合物を式(a1)のモノマー化合物と反応させる、請求項7に記載の方法。
- 前記塩基が、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、水素化ナトリウム、または水素化カリウムである、請求項8に記載の方法。
- R100 がメトキシである、請求項1〜15のいずれか一項に記載の方法。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
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US201562195023P | 2015-07-21 | 2015-07-21 | |
US62/195,023 | 2015-07-21 | ||
US201662327973P | 2016-04-26 | 2016-04-26 | |
US62/327,973 | 2016-04-26 | ||
PCT/US2016/043406 WO2017015496A1 (en) | 2015-07-21 | 2016-07-21 | Methods of preparing cytotoxic benzodiazepine derivatives |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2020180147A Division JP6995178B2 (ja) | 2015-07-21 | 2020-10-28 | 細胞毒性ベンゾジアゼピン誘導体の調製方法 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2018526340A JP2018526340A (ja) | 2018-09-13 |
JP2018526340A5 true JP2018526340A5 (ja) | 2019-08-29 |
JP6787995B2 JP6787995B2 (ja) | 2020-11-18 |
Family
ID=56557925
Family Applications (8)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018502800A Withdrawn JP2018522018A (ja) | 2015-07-21 | 2016-07-21 | 細胞毒性ベンゾジアゼピン誘導体の調製方法 |
JP2018502791A Active JP6787995B2 (ja) | 2015-07-21 | 2016-07-21 | 細胞毒性ベンゾジアゼピン誘導体の調製方法 |
JP2018502785A Active JP6858745B2 (ja) | 2015-07-21 | 2016-07-21 | 細胞毒性ベンゾジアゼピン誘導体の調製方法 |
JP2020180147A Active JP6995178B2 (ja) | 2015-07-21 | 2020-10-28 | 細胞毒性ベンゾジアゼピン誘導体の調製方法 |
JP2021049502A Active JP7337114B2 (ja) | 2015-07-21 | 2021-03-24 | 細胞毒性ベンゾジアゼピン誘導体の調製方法 |
JP2021202215A Active JP7334228B2 (ja) | 2015-07-21 | 2021-12-14 | 細胞毒性ベンゾジアゼピン誘導体の調製方法 |
JP2023132536A Pending JP2023162264A (ja) | 2015-07-21 | 2023-08-16 | 細胞毒性ベンゾジアゼピン誘導体の調製方法 |
JP2023134420A Pending JP2023166434A (ja) | 2015-07-21 | 2023-08-22 | 細胞毒性ベンゾジアゼピン誘導体の調製方法 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2018502800A Withdrawn JP2018522018A (ja) | 2015-07-21 | 2016-07-21 | 細胞毒性ベンゾジアゼピン誘導体の調製方法 |
Family Applications After (6)
Application Number | Title | Priority Date | Filing Date |
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JP2018502785A Active JP6858745B2 (ja) | 2015-07-21 | 2016-07-21 | 細胞毒性ベンゾジアゼピン誘導体の調製方法 |
JP2020180147A Active JP6995178B2 (ja) | 2015-07-21 | 2020-10-28 | 細胞毒性ベンゾジアゼピン誘導体の調製方法 |
JP2021049502A Active JP7337114B2 (ja) | 2015-07-21 | 2021-03-24 | 細胞毒性ベンゾジアゼピン誘導体の調製方法 |
JP2021202215A Active JP7334228B2 (ja) | 2015-07-21 | 2021-12-14 | 細胞毒性ベンゾジアゼピン誘導体の調製方法 |
JP2023132536A Pending JP2023162264A (ja) | 2015-07-21 | 2023-08-16 | 細胞毒性ベンゾジアゼピン誘導体の調製方法 |
JP2023134420A Pending JP2023166434A (ja) | 2015-07-21 | 2023-08-22 | 細胞毒性ベンゾジアゼピン誘導体の調製方法 |
Country Status (22)
Country | Link |
---|---|
US (11) | US9873708B2 (ja) |
EP (7) | EP3325483B1 (ja) |
JP (8) | JP2018522018A (ja) |
KR (5) | KR20240055903A (ja) |
CN (5) | CN108055844A (ja) |
AU (7) | AU2016297608B2 (ja) |
CA (4) | CA2991305C (ja) |
CY (2) | CY1122553T1 (ja) |
DK (2) | DK3325482T3 (ja) |
ES (4) | ES2959741T3 (ja) |
HK (3) | HK1252323A1 (ja) |
HR (1) | HRP20201479T1 (ja) |
HU (1) | HUE051541T2 (ja) |
IL (10) | IL305279A (ja) |
LT (2) | LT3325483T (ja) |
PL (2) | PL3325482T3 (ja) |
PT (2) | PT3325482T (ja) |
RS (2) | RS60840B1 (ja) |
RU (3) | RU2727151C2 (ja) |
SG (2) | SG10202106529XA (ja) |
SI (2) | SI3325482T1 (ja) |
WO (3) | WO2017015496A1 (ja) |
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WO2018075692A2 (en) | 2016-10-19 | 2018-04-26 | Invenra Inc. | Antibody constructs |
BR112019013107A2 (pt) | 2016-12-22 | 2019-12-17 | Univ Degli Studi Magna Graecia Catanzaro | anticorpos, molécula de ligação, receptor de antígeno quimérico, vetor de expressão, composição farmacêutica, linfócito, ácido nucleico, célula de hibridoma, método para a produção do anticorpo monoclonal e usos |
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JP2021527047A (ja) | 2018-06-05 | 2021-10-11 | キングス・カレッジ・ロンドン | 消化管系へのペイロード送達のための、btnl3/8を標的とする構築物 |
JP2022512936A (ja) * | 2018-11-12 | 2022-02-07 | イミュノジェン・インコーポレーテッド | 細胞傷害性ベンゾジアゼピン誘導体の調製方法 |
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LT3325483T (lt) * | 2015-07-21 | 2020-01-27 | Immunogen, Inc. | Citotoksinių benzodiazepino darinių gavimo būdai |
DK3380525T3 (da) * | 2015-11-25 | 2024-01-29 | Immunogen Inc | Farmaceutiske formuleringer og fremgangsmåder til anvendelse deraf |
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2016
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