CA3119358A1 - Methods of preparing cytotoxic benzodiazepine derivatives - Google Patents

Methods of preparing cytotoxic benzodiazepine derivatives Download PDF

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Publication number
CA3119358A1
CA3119358A1 CA3119358A CA3119358A CA3119358A1 CA 3119358 A1 CA3119358 A1 CA 3119358A1 CA 3119358 A CA3119358 A CA 3119358A CA 3119358 A CA3119358 A CA 3119358A CA 3119358 A1 CA3119358 A1 CA 3119358A1
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CA
Canada
Prior art keywords
compound
formula
ome
reacting
reaction
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.)
Pending
Application number
CA3119358A
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English (en)
French (fr)
Inventor
Michael Reardon
Richard A. Silva
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Immunogen Inc
Original Assignee
Immunogen Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Immunogen Inc filed Critical Immunogen Inc
Publication of CA3119358A1 publication Critical patent/CA3119358A1/en
Pending legal-status Critical Current

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Classifications

    • 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

Landscapes

  • 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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
CA3119358A 2018-11-12 2019-11-11 Methods of preparing cytotoxic benzodiazepine derivatives Pending CA3119358A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
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

Publications (1)

Publication Number Publication Date
CA3119358A1 true CA3119358A1 (en) 2020-05-22

Family

ID=68835289

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3119358A Pending CA3119358A1 (en) 2018-11-12 2019-11-11 Methods of preparing cytotoxic benzodiazepine derivatives

Country Status (12)

Country Link
US (3) US10851117B2 (enExample)
EP (2) EP4361128A3 (enExample)
JP (2) JP7437395B2 (enExample)
KR (1) KR20210098470A (enExample)
CN (2) CN118324848A (enExample)
AU (1) AU2019379104A1 (enExample)
CA (1) CA3119358A1 (enExample)
IL (1) IL283045A (enExample)
MA (1) MA54228A (enExample)
SG (1) SG11202104360YA (enExample)
TW (1) TW202033530A (enExample)
WO (1) WO2020102051A1 (enExample)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115448926A (zh) * 2017-04-20 2022-12-09 伊缪诺金公司 制备吲哚啉并苯并二氮杂䓬衍生物的方法
CA3119358A1 (en) 2018-11-12 2020-05-22 Immunogen, Inc. Methods of preparing cytotoxic benzodiazepine derivatives
AU2023298568A1 (en) 2022-06-30 2025-01-09 Toray Industries, Inc. Pharmaceutical composition for cancer treatment and/or prevention

Family Cites Families (12)

* 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
KR20140010076A (ko) 2011-02-15 2014-01-23 이뮤노젠 아이엔씨 세포독성 벤조다이아제핀 유도체
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
SMT202100092T1 (it) * 2015-06-29 2021-03-15 Immunogen Inc Anticorpi anti-cd123 e loro coniugati e derivati
MD3313845T2 (ro) * 2015-06-29 2021-02-28 Immunogen Inc Conjugați cu anticorpi având cisteină modificată prin inginerie genetică
SMT202000004T1 (it) * 2015-07-21 2020-03-13 Immunogen Inc Metodi di preparazione dei derivati citotossici di benzodiazepina
US20170189548A1 (en) * 2015-11-25 2017-07-06 Immunogen, Inc. Pharmaceutical formulations and methods of use thereof
PL3573948T3 (pl) 2017-01-25 2023-01-30 Immunogen, Inc. Sposoby otrzymywania cytotoksycznych pochodnych benzodiazepiny
EP3732178A1 (en) * 2017-12-28 2020-11-04 ImmunoGen, Inc. Benzodiazepine derivatives
CA3119358A1 (en) 2018-11-12 2020-05-22 Immunogen, Inc. Methods of preparing cytotoxic benzodiazepine derivatives

Also Published As

Publication number Publication date
EP3880681B1 (en) 2024-03-13
EP4361128A3 (en) 2024-07-17
IL283045A (en) 2021-06-30
US20210122768A1 (en) 2021-04-29
JP2024056819A (ja) 2024-04-23
KR20210098470A (ko) 2021-08-10
CN118324848A (zh) 2024-07-12
US11396519B2 (en) 2022-07-26
TW202033530A (zh) 2020-09-16
US10851117B2 (en) 2020-12-01
US11981688B2 (en) 2024-05-14
SG11202104360YA (en) 2021-05-28
EP3880681A1 (en) 2021-09-22
JP7437395B2 (ja) 2024-02-22
MA54228A (fr) 2021-09-22
EP4361128A2 (en) 2024-05-01
CN112996792A (zh) 2021-06-18
US20230045079A1 (en) 2023-02-09
CN112996792B (zh) 2024-04-26
US20200172555A1 (en) 2020-06-04
JP2022512935A (ja) 2022-02-07
WO2020102051A1 (en) 2020-05-22
WO2020102051A8 (en) 2020-06-18
AU2019379104A1 (en) 2021-06-03

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