AU2016297087B2 - Methods of preparing cytotoxic benzodiazepine derivatives - Google Patents

Methods of preparing cytotoxic benzodiazepine derivatives Download PDF

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Publication number
AU2016297087B2
AU2016297087B2 AU2016297087A AU2016297087A AU2016297087B2 AU 2016297087 B2 AU2016297087 B2 AU 2016297087B2 AU 2016297087 A AU2016297087 A AU 2016297087A AU 2016297087 A AU2016297087 A AU 2016297087A AU 2016297087 B2 AU2016297087 B2 AU 2016297087B2
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AU
Australia
Prior art keywords
formula
compound
reacting
monomer
reagent
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Ceased
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AU2016297087A
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AU2016297087A1 (en
Inventor
Baudouin GÉRARD
Michael Louis Miller
Manami Shizuka
Richard A. Silva
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Immunogen Inc
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Immunogen Inc
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Priority to AU2021203148A priority Critical patent/AU2021203148B2/en
Priority to AU2023202221A priority patent/AU2023202221A1/en
Ceased legal-status Critical Current
Anticipated expiration legal-status Critical

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    • 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
    • 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
    • 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
    • A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
    • A61K31/5517—1,4-Benzodiazepines, e.g. diazepam or clozapine condensed with five-membered rings having nitrogen as a ring hetero atom, e.g. imidazobenzodiazepines, triazolam
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
    • C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
    • 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
    • C07K5/08—Tripeptides
    • C07K5/0802—Tripeptides with the first amino acid being neutral
    • C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicinal Preparation (AREA)
  • Pyridine Compounds (AREA)
AU2016297087A 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine derivatives Ceased AU2016297087B2 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
AU2021203148A AU2021203148B2 (en) 2015-07-21 2021-05-17 Methods of preparing cytotoxic benzodiazepine derivatives
AU2023202221A AU2023202221A1 (en) 2015-07-21 2023-04-11 Methods of preparing cytotoxic benzodiazepine derivatives

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
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/US2016/043414 WO2017015502A1 (en) 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine derivatives

Related Child Applications (1)

Application Number Title Priority Date Filing Date
AU2021203148A Division AU2021203148B2 (en) 2015-07-21 2021-05-17 Methods of preparing cytotoxic benzodiazepine derivatives

Publications (2)

Publication Number Publication Date
AU2016297087A1 AU2016297087A1 (en) 2018-02-08
AU2016297087B2 true AU2016297087B2 (en) 2021-02-18

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AU2016297087A Ceased AU2016297087B2 (en) 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine derivatives
AU2016297607A Abandoned AU2016297607A1 (en) 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine derivatives
AU2016297608A Ceased AU2016297608B2 (en) 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine derivatives
AU2021202403A Ceased AU2021202403B2 (en) 2015-07-21 2021-04-20 Methods of preparing cytotoxic benzodiazepine derivatives
AU2021203148A Ceased AU2021203148B2 (en) 2015-07-21 2021-05-17 Methods of preparing cytotoxic benzodiazepine derivatives
AU2023201339A Abandoned AU2023201339A1 (en) 2015-07-21 2023-03-03 Methods of preparing cytotoxic benzodiazepine derivatives
AU2023202221A Abandoned AU2023202221A1 (en) 2015-07-21 2023-04-11 Methods of preparing cytotoxic benzodiazepine derivatives

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AU2016297607A Abandoned AU2016297607A1 (en) 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine derivatives
AU2016297608A Ceased AU2016297608B2 (en) 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine derivatives
AU2021202403A Ceased AU2021202403B2 (en) 2015-07-21 2021-04-20 Methods of preparing cytotoxic benzodiazepine derivatives
AU2021203148A Ceased AU2021203148B2 (en) 2015-07-21 2021-05-17 Methods of preparing cytotoxic benzodiazepine derivatives
AU2023201339A Abandoned AU2023201339A1 (en) 2015-07-21 2023-03-03 Methods of preparing cytotoxic benzodiazepine derivatives
AU2023202221A Abandoned AU2023202221A1 (en) 2015-07-21 2023-04-11 Methods of preparing cytotoxic benzodiazepine derivatives

Country Status (23)

Country Link
US (11) US9890179B2 (https=)
EP (7) EP3653628B1 (https=)
JP (8) JP6858745B2 (https=)
KR (5) KR20240055894A (https=)
CN (5) CN108290895B (https=)
AU (7) AU2016297087B2 (https=)
CA (4) CA3227588A1 (https=)
CY (2) CY1122553T1 (https=)
DK (2) DK3325482T3 (https=)
ES (4) ES2959741T3 (https=)
HK (1) HK1252322A1 (https=)
HR (1) HRP20201479T1 (https=)
HU (1) HUE051541T2 (https=)
IL (10) IL286788B2 (https=)
LT (2) LT3325483T (https=)
PL (2) PL3325482T3 (https=)
PT (2) PT3325483T (https=)
RS (2) RS60840B1 (https=)
RU (3) RU2018105752A (https=)
SG (2) SG10202106529XA (https=)
SI (2) SI3325482T1 (https=)
SM (2) SMT202000506T1 (https=)
WO (3) WO2017015496A1 (https=)

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SG10202106529XA (en) * 2015-07-21 2021-07-29 Immunogen Inc Methods of preparing cytotoxic benzodiazepine derivatives
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KR20240000650A (ko) 2016-10-19 2024-01-02 인벤라 인코포레이티드 항체 구조물
EP3559039A1 (en) 2016-12-22 2019-10-30 Università Degli Studi Magna Graecia Catanzaro A monoclonal antibody targeting a unique sialoglycosilated cancer-associated epitope of cd43
EP4148044A1 (en) 2017-01-25 2023-03-15 ImmunoGen, Inc. Methods of preparing cytotoxic benzodiazepine derivatives
WO2019234136A1 (en) 2018-06-05 2019-12-12 King's College London Btnl3/8 targeting constructs for delivery of payloads to the gastrointestinal system
KR20210098470A (ko) * 2018-11-12 2021-08-10 이뮤노젠 아이엔씨 세포독성 벤조디아제핀 유도체의 제조 방법
TWI849000B (zh) * 2018-11-12 2024-07-21 美商伊繆諾金公司 製備細胞毒性苯二氮呯衍生物之方法
EP3947395A1 (en) * 2019-03-29 2022-02-09 ImmunoGen, Inc. Cytotoxic bis-benzodiazepine derivatives and conjugates thereof with cell-binding agents for inhibiting abnormal cell growth or for treating proliferative diseases
KR20250031149A (ko) 2022-06-30 2025-03-06 도레이 카부시키가이샤 암의 치료 및/또는 예방용 의약 조성물

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