CA2991305C - Methods of preparing cytotoxic benzodiazepine derivatives - Google Patents

Methods of preparing cytotoxic benzodiazepine derivatives Download PDF

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Publication number
CA2991305C
CA2991305C CA2991305A CA2991305A CA2991305C CA 2991305 C CA2991305 C CA 2991305C CA 2991305 A CA2991305 A CA 2991305A CA 2991305 A CA2991305 A CA 2991305A CA 2991305 C CA2991305 C CA 2991305C
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Canada
Prior art keywords
formula
compound
reacting
monomer
reagent
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CA2991305A
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English (en)
French (fr)
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CA2991305A1 (en
Inventor
Baudouin Gerard
Manami Shizuka
Michael Louis Miller
Richard A. Silva
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Immunogen Inc
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Immunogen Inc
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Priority to CA3227588A priority Critical patent/CA3227588A1/en
Publication of CA2991305A1 publication Critical patent/CA2991305A1/en
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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
    • 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
    • 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
    • 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
    • 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)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (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 That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Medicinal Preparation (AREA)
  • Pyridine Compounds (AREA)
CA2991305A 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine derivatives Active CA2991305C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA3227588A CA3227588A1 (en) 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine deravatives

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
CA3227588A Division CA3227588A1 (en) 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine deravatives

Publications (2)

Publication Number Publication Date
CA2991305A1 CA2991305A1 (en) 2017-01-26
CA2991305C true CA2991305C (en) 2024-03-12

Family

ID=56557925

Family Applications (4)

Application Number Title Priority Date Filing Date
CA2991305A Active CA2991305C (en) 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine derivatives
CA2992082A Pending CA2992082A1 (en) 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine derivatives
CA3227588A Pending CA3227588A1 (en) 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine deravatives
CA2991326A Abandoned CA2991326A1 (en) 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine derivatives

Family Applications After (3)

Application Number Title Priority Date Filing Date
CA2992082A Pending CA2992082A1 (en) 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine derivatives
CA3227588A Pending CA3227588A1 (en) 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine deravatives
CA2991326A Abandoned CA2991326A1 (en) 2015-07-21 2016-07-21 Methods of preparing cytotoxic benzodiazepine derivatives

Country Status (23)

Country Link
US (11) US9890179B2 (enExample)
EP (7) EP3778602B1 (enExample)
JP (8) JP6858745B2 (enExample)
KR (5) KR20240055903A (enExample)
CN (5) CN108026103B (enExample)
AU (7) AU2016297607A1 (enExample)
CA (4) CA2991305C (enExample)
CY (2) CY1122553T1 (enExample)
DK (2) DK3325482T3 (enExample)
ES (4) ES2933376T3 (enExample)
HK (1) HK1252322A1 (enExample)
HR (1) HRP20201479T1 (enExample)
HU (1) HUE051541T2 (enExample)
IL (10) IL305279A (enExample)
LT (2) LT3325483T (enExample)
PL (2) PL3325483T3 (enExample)
PT (2) PT3325482T (enExample)
RS (2) RS60840B1 (enExample)
RU (3) RU2746322C2 (enExample)
SG (2) SG10202009354SA (enExample)
SI (2) SI3325483T1 (enExample)
SM (2) SMT202000004T1 (enExample)
WO (3) WO2017015495A1 (enExample)

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Publication number Publication date
EP3325485B1 (en) 2020-04-08
CN113087763A (zh) 2021-07-09
CA2991305A1 (en) 2017-01-26
CA2992082A1 (en) 2017-01-26
JP2018526340A (ja) 2018-09-13
RU2018105752A (ru) 2019-08-21
JP2018522018A (ja) 2018-08-09
IL276631B (en) 2021-10-31
CN108026103B (zh) 2021-04-16
CN108290895A (zh) 2018-07-17
CN108055844A (zh) 2018-05-18
JP2022046542A (ja) 2022-03-23
JP6995178B2 (ja) 2022-02-21
US20170051011A1 (en) 2017-02-23
IL256854A (en) 2018-03-29
WO2017015496A1 (en) 2017-01-26
HK1252321A1 (en) 2019-05-24
JP7334228B2 (ja) 2023-08-28
US10392407B2 (en) 2019-08-27
SMT202000004T1 (it) 2020-03-13
US10899775B2 (en) 2021-01-26
KR102659706B1 (ko) 2024-04-23
ES2959741T3 (es) 2024-02-28
US20210171547A1 (en) 2021-06-10
HUE051541T2 (hu) 2021-03-01
JP2021100959A (ja) 2021-07-08
CA2991326A1 (en) 2017-01-26
IL276631A (en) 2020-09-30
AU2021203148B2 (en) 2023-01-12
KR102660070B1 (ko) 2024-04-24
IL283355B (en) 2022-08-01
AU2021202403A1 (en) 2021-05-20
IL276630A (en) 2020-09-30
US20170050985A1 (en) 2017-02-23
EP3778602B1 (en) 2023-07-12
CY1122553T1 (el) 2021-01-27
IL286788B2 (en) 2024-01-01
AU2016297087B2 (en) 2021-02-18
IL256860A (en) 2018-03-29
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