CA3073766A1 - Process for the preparation of tubulysins and intermediates thereof - Google Patents

Process for the preparation of tubulysins and intermediates thereof Download PDF

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Publication number
CA3073766A1
CA3073766A1 CA3073766A CA3073766A CA3073766A1 CA 3073766 A1 CA3073766 A1 CA 3073766A1 CA 3073766 A CA3073766 A CA 3073766A CA 3073766 A CA3073766 A CA 3073766A CA 3073766 A1 CA3073766 A1 CA 3073766A1
Authority
CA
Canada
Prior art keywords
intermediates
preparation
tubulysins
tubulysin
compounds
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
CA3073766A
Other languages
English (en)
French (fr)
Inventor
Kun-liang WU
Qingwu Jin
Wendel Doubleday
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.)
Seagen Inc
Original Assignee
Seattle Genetics 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 Seattle Genetics Inc filed Critical Seattle Genetics Inc
Publication of CA3073766A1 publication Critical patent/CA3073766A1/en
Pending legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6835—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site
    • A61K47/6851—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment the modifying agent being an antibody or an immunoglobulin bearing at least one antigen-binding site the antibody targeting a determinant of a tumour cell
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
    • A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
    • A61K47/6811—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug being a protein or peptide, e.g. transferrin or bleomycin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6801—Drug-antibody or immunoglobulin conjugates defined by the pharmacologically or therapeutically active agent
    • A61K47/6803—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates
    • A61K47/6811—Drugs conjugated to an antibody or immunoglobulin, e.g. cisplatin-antibody conjugates the drug being a protein or peptide, e.g. transferrin or bleomycin
    • A61K47/6817—Toxins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/68—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an antibody, an immunoglobulin or a fragment thereof, e.g. an Fc-fragment
    • A61K47/6889—Conjugates wherein the antibody being the modifying agent and wherein the linker, binder or spacer confers particular properties to the conjugates, e.g. peptidic enzyme-labile linkers or acid-labile linkers, providing for an acid-labile immuno conjugate wherein the drug may be released from its antibody conjugated part in an acidic, e.g. tumoural or environment
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
    • C07K5/021—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-(X)n-C(=0)-, n being 5 or 6; for n > 6, classification in C07K5/06 - C07K5/10, according to the moiety having normal peptide bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Immunology (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Toxicology (AREA)
  • Cell Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Thiazole And Isothizaole Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
CA3073766A 2017-09-08 2018-09-07 Process for the preparation of tubulysins and intermediates thereof Pending CA3073766A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201762556234P 2017-09-08 2017-09-08
US62/556,234 2017-09-08
PCT/US2018/050095 WO2019051322A1 (en) 2017-09-08 2018-09-07 PROCESS FOR THE PREPARATION OF TUBULYSINS AND INTERMEDIATES THEREOF

Publications (1)

Publication Number Publication Date
CA3073766A1 true CA3073766A1 (en) 2019-03-14

Family

ID=63963374

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3073766A Pending CA3073766A1 (en) 2017-09-08 2018-09-07 Process for the preparation of tubulysins and intermediates thereof

Country Status (15)

Country Link
US (2) US11389543B2 (enExample)
EP (1) EP3679036A1 (enExample)
JP (2) JP2020533308A (enExample)
KR (1) KR20200051733A (enExample)
CN (1) CN111601803A (enExample)
AU (1) AU2018329951B2 (enExample)
BR (1) BR112020004495A2 (enExample)
CA (1) CA3073766A1 (enExample)
EA (1) EA202090670A1 (enExample)
IL (1) IL272837B2 (enExample)
MA (1) MA50124A (enExample)
MX (1) MX2020001928A (enExample)
SG (1) SG11202001543XA (enExample)
TW (2) TWI820038B (enExample)
WO (1) WO2019051322A1 (enExample)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111601803A (zh) * 2017-09-08 2020-08-28 西雅图基因公司 微管溶素及其中间体的制备方法
US20230002440A1 (en) * 2018-09-07 2023-01-05 Seattle Genetics, Inc. Alternative processes for the preparation of tubulysins and intermediates thereof
CA3213636A1 (en) 2021-03-18 2022-09-22 Seagen Inc. Selective drug release from internalized conjugates of biologically active compounds

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10230872A1 (de) * 2002-07-09 2004-01-22 Morphochem AG Aktiengesellschaft für kombinatorische Chemie Verfahren zur Herstellung von substituierten Thiazol-2-ylmethylestern
JP5171621B2 (ja) 2005-07-07 2013-03-27 シアトル ジェネティックス， インコーポレイテッド フェニルアラニン側鎖修飾をｃ末端に有するモノメチルバリン化合物
WO2007140371A2 (en) 2006-05-30 2007-12-06 Genentech, Inc. Antibodies and immunoconjugates and uses therefor
CA2678941C (en) 2007-02-23 2018-11-27 Aileron Therapeutics, Inc. Triazole macrocycle systems
WO2008106080A2 (en) * 2007-02-27 2008-09-04 University Of Pittsburgh - Of The Commonwealth System Of Higher Education Synthesis of desacetoxytubulysin h and analogs thereof
AU2013229786B2 (en) 2012-03-08 2017-06-22 Halozyme, Inc. Conditionally active anti-epidermal growth factor receptor antibodies and methods of use thereof
EP3925627A1 (en) 2012-05-15 2021-12-22 Concortis Biosystems, Corp Drug-conjugates and uses thereof
AU2013263002C1 (en) 2012-05-15 2018-05-31 Seagen Inc. Self-stabilizing linker conjugates
EP2708243A1 (en) * 2012-09-17 2014-03-19 OntoChem GmbH Receptor ligand linked cytotoxic molecules
MA38686A1 (fr) 2013-05-31 2017-10-31 Genentech Inc Anticorps anti-acide téichoïque de la paroi cellulaire et conjugués associés
BR112015029754A2 (pt) 2013-05-31 2017-09-26 Genentech Inc anticorpos anti-teicoico da parede e conjugados
HRP20241124T1 (hr) * 2014-09-11 2024-11-22 Seagen Inc. Ciljana isporuka lijekovitih tvari koje sadrže tercijarni amin
MX2017007169A (es) 2014-12-03 2018-05-02 Genentech Inc Compuestos de amina cuaternaria y conjugados de anticuerpofármaco de los mismos.
EA201791896A1 (ru) * 2015-02-25 2018-02-28 Уильям Марш Райс Юниверсити Дезацетокситубулизин н и его аналоги
CN111601803A (zh) * 2017-09-08 2020-08-28 西雅图基因公司 微管溶素及其中间体的制备方法

Also Published As

Publication number Publication date
MA50124A (fr) 2020-07-15
IL272837B1 (en) 2024-02-01
SG11202001543XA (en) 2020-03-30
TW201920128A (zh) 2019-06-01
MX2020001928A (es) 2020-03-24
EP3679036A1 (en) 2020-07-15
JP2020533308A (ja) 2020-11-19
KR20200051733A (ko) 2020-05-13
EA202090670A1 (ru) 2020-07-28
US11389543B2 (en) 2022-07-19
BR112020004495A2 (pt) 2020-09-08
IL272837B2 (en) 2024-06-01
AU2018329951A1 (en) 2020-04-16
IL272837A (en) 2020-04-30
US20220323601A1 (en) 2022-10-13
AU2018329951B2 (en) 2023-12-14
TW202428569A (zh) 2024-07-16
WO2019051322A1 (en) 2019-03-14
JP2023053386A (ja) 2023-04-12
US20200297864A1 (en) 2020-09-24
TWI820038B (zh) 2023-11-01
CN111601803A (zh) 2020-08-28

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