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

Info

Publication number
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
Authority
CN
China
Prior art keywords
compound
formula
reacting
cyanuric chloride
iia
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.)
Expired - Fee Related
Application number
CN201980074241.1A
Other languages
English (en)
Chinese (zh)
Other versions
CN112996792A (zh
Inventor
M·里尔登
R·A·西尔瓦
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
Priority to CN202410421643.7A priority Critical patent/CN118324848A/zh
Publication of CN112996792A publication Critical patent/CN112996792A/zh
Application granted granted Critical
Publication of CN112996792B publication Critical patent/CN112996792B/zh
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

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)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Peptides Or Proteins (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)
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)

Priority Applications (1)

Application Number Priority Date Filing Date Title
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

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

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CN202410421643.7A Division 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

Publications (2)

Publication Number Publication Date
CN112996792A CN112996792A (zh) 2021-06-18
CN112996792B true CN112996792B (zh) 2024-04-26

Family

ID=68835289

Family Applications (2)

Application Number Title Priority Date Filing Date
CN201980074241.1A Expired - Fee Related CN112996792B (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
CN202410421643.7A Pending 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

Family Applications After (1)

Application Number Title Priority Date Filing Date
CN202410421643.7A Pending 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

Country Status (12)

Country Link
US (3) US10851117B2 (enExample)
EP (2) EP3880681B1 (enExample)
JP (2) JP7437395B2 (enExample)
KR (1) KR20210098470A (enExample)
CN (2) CN112996792B (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
IL305224B2 (en) * 2017-04-20 2024-09-01 Immunogen Inc Methods of preparing indolinobenzodiazepine derivatives
MA54228A (fr) 2018-11-12 2021-09-22 Immunogen Inc Procédés de préparation de dérivés de benzodiazépine cytotoxiques
EP4548932A1 (en) 2022-06-30 2025-05-07 Toray Industries, Inc. Pharmaceutical composition for treating and/or preventing cancer

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
JP5826863B2 (ja) 2011-02-15 2015-12-02 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
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
SMT202000614T1 (it) * 2015-06-29 2021-01-05 Immunogen Inc Coniugati di anticorpi ingegnerizzati con cisteina
AU2016285552B2 (en) * 2015-06-29 2022-10-13 Immunogen, Inc. Anti-CD123 antibodies and conjugates and derivatives thereof
US20170189548A1 (en) * 2015-11-25 2017-07-06 Immunogen, Inc. Pharmaceutical formulations and methods of use thereof
EP4148044A1 (en) * 2017-01-25 2023-03-15 ImmunoGen, Inc. Methods of preparing cytotoxic benzodiazepine derivatives
US11793885B2 (en) * 2017-12-28 2023-10-24 Immunogen, Inc. Substituted benzo[5,6][1,4]diazepino[1,2-a]indoles for the treatment of proliferative disorders
MA54228A (fr) 2018-11-12 2021-09-22 Immunogen Inc Procédés de préparation de dérivés de benzodiazépine cytotoxiques

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 *

Also Published As

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

Similar Documents

Publication Publication Date Title
CN112996792B (zh) 制备细胞毒性苯并二氮杂卓衍生物的方法
KR102490955B1 (ko) 약제의 제조 방법
US10392407B2 (en) Methods of preparing cytotoxic benzodiazepine derivatives
CA2966800C (en) Synthesis of copanlisib and its dihydrochloride salt
CN104136399B (zh) 泛素活化酶的吡唑并嘧啶基抑制剂
CN110225904B (zh) 制备细胞毒性苯二氮䓬衍生物的方法
TWI863110B (zh) 用於製備選擇性雌激素受體降解劑之方法
KR20210014646A (ko) 키랄 2-[(헤테로)아릴알킬설파닐]피리미딘의 입체선택성 제조 공정 및 이로부터 얻을 수 있는 생성물
RU2813137C2 (ru) Способы получения цитотоксических производных бензодиазепина
KR20210081369A (ko) 1,2,3,4-테트라히드로퀴녹살린 유도체, 이의 제조 방법 및 응용
JP2025517323A (ja) Ｃｆｔｒモジュレーターとしての大環状化合物の固体形態及びその調製
AU2018232211A1 (en) Radioactive fluorine-labeling precursor compound and method for producing radioactive fluorine-labeled compound using same
Rammohan et al. Reactions of 4, 5-Dimethyl-1, 2-dehydrobenzene with 6-Aryl-3-(2-pyridyl)-1, 2, 4-triazines
CN103965198A (zh) 替卡格雷的中间体及其制备方法以及利用该中间体制备替卡格雷的方法
Diab El Harakeh Synthesis and characterization of triazine-based compounds as potential precursors for hydrogen-bonded organic frameworks (HOFs)
EP4592286A1 (en) Macrocyclic nitrogen-containing crown ether compound and use thereof as protein kinase inhibitor
HK40044947B (zh) 氨基嘧啶的制备方法和其中间体
Hollá Synthesis of polycyclic lactones and lactams
NZ747420A (en) [1,2,3]triazolo[4,5-d]pyrimidine derivatives with affinity for the type-2 cannabinoid receptor
KR20150108515A (ko) 피리미딘, 피라졸 및 피라졸로피리미딘 융합된 카보하이브리드 헤테로고리 화합물 라이브러리 및 이의 제조방법

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20240426

CF01 Termination of patent right due to non-payment of annual fee