CN112996792B - 制备细胞毒性苯并二氮杂卓衍生物的方法 - Google Patents

制备细胞毒性苯并二氮杂卓衍生物的方法 Download PDF

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CN112996792B
CN112996792B CN201980074241.1A CN201980074241A CN112996792B CN 112996792 B CN112996792 B CN 112996792B CN 201980074241 A CN201980074241 A CN 201980074241A CN 112996792 B CN112996792 B CN 112996792B
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compound
formula
reacting
cyanuric chloride
iia
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CN112996792A (zh
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M·里尔登
R·A·西尔瓦
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Immunogen Inc
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Immunogen Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/07—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C237/22—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/22—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of hydropolysulfides or polysulfides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
    • C07C321/20—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
    • C07C323/24—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/25—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Genetics & Genomics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Peptides Or Proteins (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CN201980074241.1A 2018-11-12 2019-11-11 制备细胞毒性苯并二氮杂卓衍生物的方法 Expired - Fee Related CN112996792B (zh)

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CN202410421643.7A CN118324848A (zh) 2018-11-12 2019-11-11 制备细胞毒性苯并二氮杂卓衍生物的方法

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US201862758814P 2018-11-12 2018-11-12
US62/758,814 2018-11-12
PCT/US2019/060677 WO2020102051A1 (en) 2018-11-12 2019-11-11 Methods of preparing cytotoxic benzodiazepine derivatives

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US (3) US10851117B2 (cg-RX-API-DMAC10.html)
EP (2) EP3880681B1 (cg-RX-API-DMAC10.html)
JP (2) JP7437395B2 (cg-RX-API-DMAC10.html)
KR (1) KR20210098470A (cg-RX-API-DMAC10.html)
CN (2) CN112996792B (cg-RX-API-DMAC10.html)
AU (1) AU2019379104A1 (cg-RX-API-DMAC10.html)
CA (1) CA3119358A1 (cg-RX-API-DMAC10.html)
IL (1) IL283045A (cg-RX-API-DMAC10.html)
MA (1) MA54228A (cg-RX-API-DMAC10.html)
SG (1) SG11202104360YA (cg-RX-API-DMAC10.html)
TW (1) TW202033530A (cg-RX-API-DMAC10.html)
WO (1) WO2020102051A1 (cg-RX-API-DMAC10.html)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3612533A1 (en) * 2017-04-20 2020-02-26 Immunogen, Inc. Methods of preparing indolinobenzodiazepine derivatives
CN112996792B (zh) 2018-11-12 2024-04-26 伊缪诺金公司 制备细胞毒性苯并二氮杂卓衍生物的方法
AU2023298568A1 (en) 2022-06-30 2025-01-09 Toray Industries, Inc. Pharmaceutical composition for cancer treatment and/or prevention

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4902707A (en) * 1985-04-30 1990-02-20 Eli Lilly And Company Bicyclic pyrazolidinones, compositions and use
US5015738A (en) * 1989-08-07 1991-05-14 Hoechst-Roussel Pharmaceuticals Inc. Benzo(b)pyrrolobenzodiazepines
CN102050824A (zh) * 2009-11-04 2011-05-11 上海阳帆医药科技有限公司 哌嗪并三唑衍生物
CN108026103A (zh) * 2015-07-21 2018-05-11 伊缪诺金公司 制备细胞毒性苯并二氮杂䓬衍生物的方法

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SI2675480T1 (sl) 2011-02-15 2019-05-31 Immunogen, Inc. Metode priprave konjugatov
RU2539658C1 (ru) 2013-12-10 2015-01-20 Федеральное государственное казенное учреждение "33 Центральный научно-исследовательский испытательный институт Министерства обороны Российской Федерации" Способ получения бензилхлорида
SI3313845T1 (sl) * 2015-06-29 2021-01-29 Immunogen, Inc. Konjugati spremenjenih protiteles cisteina
SMT202100092T1 (it) * 2015-06-29 2021-03-15 Immunogen Inc Anticorpi anti-cd123 e loro coniugati e derivati
RS65120B1 (sr) * 2015-11-25 2024-02-29 Immunogen Inc Farmaceutske formulacije i postupci za njihovu upotrebu
HRP20230002T1 (hr) 2017-01-25 2023-02-17 Immunogen, Inc. Postupci pripreme citotoksičnih derivata benzodiazepina
WO2019133652A1 (en) * 2017-12-28 2019-07-04 Immunogen, Inc. Benzodiazepine derivatives
CN112996792B (zh) 2018-11-12 2024-04-26 伊缪诺金公司 制备细胞毒性苯并二氮杂卓衍生物的方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4902707A (en) * 1985-04-30 1990-02-20 Eli Lilly And Company Bicyclic pyrazolidinones, compositions and use
US5015738A (en) * 1989-08-07 1991-05-14 Hoechst-Roussel Pharmaceuticals Inc. Benzo(b)pyrrolobenzodiazepines
CN102050824A (zh) * 2009-11-04 2011-05-11 上海阳帆医药科技有限公司 哌嗪并三唑衍生物
CN108026103A (zh) * 2015-07-21 2018-05-11 伊缪诺金公司 制备细胞毒性苯并二氮杂䓬衍生物的方法
CN108055844A (zh) * 2015-07-21 2018-05-18 伊缪诺金公司 制备细胞毒性苯并二氮杂*衍生物的方法

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
"A General Catalytic Method for Highly Cost- and Atom-Efficient Nucleophilic Substitutions"及其Supporting Information;Peter H. Huy等;《Chem. Eur. J.》;第24卷;第7410-7416页其Supporting Information第S1-S156页 *
"Synthesis of a new class of unsymmetrical PCP’ pincer ligands and their palladium (II) complexes: X-ray structure determination of PdCl{C6H3-2-CH2PPh2-6-CH2PBut2}";Ali Naghipour等;《Journal of Organometallic Chemistry》;第689卷;第2494-2502页 *

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IL283045A (en) 2021-06-30
SG11202104360YA (en) 2021-05-28
EP4361128A2 (en) 2024-05-01
US10851117B2 (en) 2020-12-01
MA54228A (fr) 2021-09-22
WO2020102051A8 (en) 2020-06-18
JP2022512935A (ja) 2022-02-07
TW202033530A (zh) 2020-09-16
CN118324848A (zh) 2024-07-12
KR20210098470A (ko) 2021-08-10
WO2020102051A1 (en) 2020-05-22
EP3880681B1 (en) 2024-03-13
US20200172555A1 (en) 2020-06-04
CN112996792A (zh) 2021-06-18
US20210122768A1 (en) 2021-04-29
CA3119358A1 (en) 2020-05-22
US20230045079A1 (en) 2023-02-09
US11981688B2 (en) 2024-05-14
EP4361128A3 (en) 2024-07-17
US11396519B2 (en) 2022-07-26
JP2024056819A (ja) 2024-04-23
EP3880681A1 (en) 2021-09-22
AU2019379104A1 (en) 2021-06-03
JP7437395B2 (ja) 2024-02-22

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