JP7402159B2 - 薬物リンカー化合物の調製のためのプロセス - Google Patents

薬物リンカー化合物の調製のためのプロセス Download PDF

Info

Publication number
JP7402159B2
JP7402159B2 JP2020529321A JP2020529321A JP7402159B2 JP 7402159 B2 JP7402159 B2 JP 7402159B2 JP 2020529321 A JP2020529321 A JP 2020529321A JP 2020529321 A JP2020529321 A JP 2020529321A JP 7402159 B2 JP7402159 B2 JP 7402159B2
Authority
JP
Japan
Prior art keywords
compound
formula
salt
alkyl
group
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.)
Active
Application number
JP2020529321A
Other languages
English (en)
Japanese (ja)
Other versions
JP2021505542A5 (https=
JP2021505542A (ja
Inventor
ソフィー ブランチャード，
ジェームズ コーツ，
Original Assignee
シージェン インコーポレイテッド
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 シージェン インコーポレイテッド filed Critical シージェン インコーポレイテッド
Publication of JP2021505542A publication Critical patent/JP2021505542A/ja
Publication of JP2021505542A5 publication Critical patent/JP2021505542A5/ja
Priority to JP2023152281A priority Critical patent/JP7787859B2/ja
Application granted granted Critical
Publication of JP7402159B2 publication Critical patent/JP7402159B2/ja
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

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
    • A61K47/6889—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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • 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
    • A61K47/62—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 a protein, peptide or polyamino acid
    • A61K47/65—Peptidic linkers, binders or spacers, e.g. peptidic enzyme-labile linkers
    • 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
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
    • C07K1/10—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using coupling agents
    • 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
    • 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
    • C07K5/06034—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms
    • C07K5/06052—Val-amino acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
    • C07K7/02—Linear peptides containing at least one abnormal peptide link

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (AREA)
  • Biophysics (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Immunology (AREA)
  • Analytical Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Peptides Or Proteins (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicinal Preparation (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
JP2020529321A 2017-11-30 2018-11-29 薬物リンカー化合物の調製のためのプロセス Active JP7402159B2 (ja)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2023152281A JP7787859B2 (ja) 2017-11-30 2023-09-20 薬物リンカー化合物の調製のためのプロセス

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201762593104P 2017-11-30 2017-11-30
US62/593,104 2017-11-30
PCT/US2018/063070 WO2019108797A1 (en) 2017-11-30 2018-11-29 Process for the preparation of drug linker compounds

Related Child Applications (1)

Application Number Title Priority Date Filing Date
JP2023152281A Division JP7787859B2 (ja) 2017-11-30 2023-09-20 薬物リンカー化合物の調製のためのプロセス

Publications (3)

Publication Number Publication Date
JP2021505542A JP2021505542A (ja) 2021-02-18
JP2021505542A5 JP2021505542A5 (https=) 2022-01-06
JP7402159B2 true JP7402159B2 (ja) 2023-12-20

Family

ID=66665808

Family Applications (2)

Application Number Title Priority Date Filing Date
JP2020529321A Active JP7402159B2 (ja) 2017-11-30 2018-11-29 薬物リンカー化合物の調製のためのプロセス
JP2023152281A Active JP7787859B2 (ja) 2017-11-30 2023-09-20 薬物リンカー化合物の調製のためのプロセス

Family Applications After (1)

Application Number Title Priority Date Filing Date
JP2023152281A Active JP7787859B2 (ja) 2017-11-30 2023-09-20 薬物リンカー化合物の調製のためのプロセス

Country Status (15)

Country Link
US (2) US11612666B2 (https=)
EP (1) EP3717016A4 (https=)
JP (2) JP7402159B2 (https=)
KR (2) KR20250024092A (https=)
CN (2) CN111417408B (https=)
AU (1) AU2018375412B2 (https=)
BR (1) BR112020010503A2 (https=)
CA (1) CA3082165A1 (https=)
EA (1) EA202091340A1 (https=)
IL (1) IL274757B2 (https=)
MA (1) MA51870A (https=)
MX (2) MX2020005565A (https=)
SG (1) SG11202004698RA (https=)
WO (1) WO2019108797A1 (https=)
ZA (1) ZA202003037B (https=)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7167163B2 (ja) * 2019-05-20 2022-11-08 煙台邁百瑞国際生物医薬股▲ふん▼有限公司 抗体－薬物コンジュゲートの中間体のワンポット合成法による製造プロセス
CN110945009B (zh) * 2019-10-23 2023-10-31 烟台迈百瑞国际生物医药股份有限公司 一种寡肽连接子中间体及其制备方法
AU2022238571A1 (en) 2021-03-18 2023-09-14 Seagen Inc. Selective drug release from internalized conjugates of biologically active compounds
CN115873066A (zh) * 2022-07-27 2023-03-31 吉林省博大伟业制药有限公司 一种抗体偶联药物连接子的合成方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007514652A (ja) 2003-11-06 2007-06-07 シアトル ジェネティックス， インコーポレイテッド リガンドに結合体化可能なモノメチルバリン化合物
JP2010530428A (ja) 2007-06-21 2010-09-09 アムゲン インコーポレイティッド シナカルセトおよびその塩を合成する方法
JP2014516050A (ja) 2011-05-27 2014-07-07 アンブルックス，インコーポレイテッド 非天然アミノ酸結合ドラスタチン誘導体を含有する組成物、それを用いた方法、およびその使用
JP2016501244A (ja) 2012-12-07 2016-01-18 バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ Ａｔｒキナーゼ阻害剤として有用な化合物
JP2016526042A (ja) 2013-05-31 2016-09-01 ファルマ、マール、ソシエダード、アノニマＰｈａｒｍａ Ｍｒｓ，Ｓ．Ａ． 抗体薬物コンジュゲート

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6214345B1 (en) * 1993-05-14 2001-04-10 Bristol-Myers Squibb Co. Lysosomal enzyme-cleavable antitumor drug conjugates
WO2007031734A1 (en) * 2005-09-14 2007-03-22 Ucb Pharma S.A. Comb polymers
MX2009002855A (es) * 2006-09-15 2009-03-30 Enzon Pharmaceuticals Inc Profarmacos polimericos dirigidos que contienen enlazadores multifuncionales.
US9981046B2 (en) * 2012-05-15 2018-05-29 Concortis Biosystems, Corp., a wholly owned Subsidiary of Sorrento Therapeutics, Inc. Drug-conjugates, conjugation methods, and uses thereof
GB201416960D0 (en) * 2014-09-25 2014-11-12 Antikor Biopharma Ltd Biological materials and uses thereof
US9533483B2 (en) 2014-09-26 2017-01-03 Kimberly-Clark Worldwide, Inc. Apparatus for and method of shaping and applying a segment to a moving web

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2007514652A (ja) 2003-11-06 2007-06-07 シアトル ジェネティックス， インコーポレイテッド リガンドに結合体化可能なモノメチルバリン化合物
JP2010530428A (ja) 2007-06-21 2010-09-09 アムゲン インコーポレイティッド シナカルセトおよびその塩を合成する方法
JP2014516050A (ja) 2011-05-27 2014-07-07 アンブルックス，インコーポレイテッド 非天然アミノ酸結合ドラスタチン誘導体を含有する組成物、それを用いた方法、およびその使用
JP2016501244A (ja) 2012-12-07 2016-01-18 バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ Ａｔｒキナーゼ阻害剤として有用な化合物
JP2016526042A (ja) 2013-05-31 2016-09-01 ファルマ、マール、ソシエダード、アノニマＰｈａｒｍａ Ｍｒｓ，Ｓ．Ａ． 抗体薬物コンジュゲート

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
George R. PETTIT et al.，"Antineoplastic Agents. 604. The Path of Quinstatin Derivatives to Antibody Drug Conjugates"，Journal of Natural Products，2017年09月12日，Vol. 80, No. 9，p.2447-2452，DOI: 10.1021/acs.jnatprod.7b00237
Jun LU et al.，"Linkers Having a Crucial Role in Antibody-Drug Conjugates"，International Journal of Molecular Sciences，2016年04月14日，Vol. 17, No. 4，p.561，DOI: 10.3390/ijms17040561
Sergii KOLODYCH et al.，"Development and evaluation of β-galactosidase-sensitive antibody-drug conjugates"，European Journal of Medicinal Chemistry，2017年12月，Vol. 142，p.376-382，DOI: 10.1016/j.ejmech.2017.08.008
Tetrahedron，2004年，Vol.60，p.2447-2467

Also Published As

Publication number Publication date
KR102762352B1 (ko) 2025-02-05
CN111417408B (zh) 2024-04-23
BR112020010503A2 (pt) 2020-10-20
US20200360532A1 (en) 2020-11-19
MX2020005565A (es) 2020-08-20
KR20250024092A (ko) 2025-02-18
CN118271394A (zh) 2024-07-02
JP2023164652A (ja) 2023-11-10
SG11202004698RA (en) 2020-06-29
KR20200094185A (ko) 2020-08-06
JP7787859B2 (ja) 2025-12-17
MX2023009372A (es) 2023-08-16
WO2019108797A1 (en) 2019-06-06
EP3717016A4 (en) 2021-09-01
IL274757B1 (en) 2025-12-01
IL274757A (en) 2020-07-30
CA3082165A1 (en) 2019-06-06
US11612666B2 (en) 2023-03-28
MA51870A (fr) 2020-10-07
CN111417408A (zh) 2020-07-14
EP3717016A1 (en) 2020-10-07
JP2021505542A (ja) 2021-02-18
EA202091340A1 (ru) 2020-10-16
IL274757B2 (en) 2026-04-01
US20240042052A1 (en) 2024-02-08
AU2018375412A1 (en) 2020-05-28
ZA202003037B (en) 2023-12-20
AU2018375412B2 (en) 2025-01-02

Similar Documents

Publication Publication Date Title
JP7787859B2 (ja) 薬物リンカー化合物の調製のためのプロセス
TWI839055B (zh) 聚乙二醇化的藥物－連接劑及其中間體
JP7527787B2 (ja) グルクロニド薬物－リンカーの調製のためのプロセスおよびその中間体
KR20230137295A (ko) 접합체 및 이의 용도
HK40112601A (zh) 药物接头化合物的制备方法
TW202517641A (zh) 咪唑並喹啉胺類衍生物的藥物共軛物、組合物以及其方法
HK40033820A (en) Process for the preparation of drug linker compounds
HK40033820B (zh) 药物接头化合物的制备方法
EA044354B1 (ru) Способ получения соединений "лекарственное средство-линкер"
TW202334176A (zh) 新穎的澳瑞他汀(auristatin)類似物及其免疫綴合物
WO2018045245A1 (en) Cyclic peptide analogs and conjugates thereof
EA047735B1 (ru) Способ получения пегилированных соединений лекарственный препарат-линкер и их промежуточных соединений
HK40009733A (en) Process for the preparation of pegylated drug-linkers and intermediates thereof
HK40016637A (en) Process for the preparation of glucuronide drug-linkers and intermediates thereof

Legal Events

Date Code Title Description
A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20211126

A621 Written request for application examination

Free format text: JAPANESE INTERMEDIATE CODE: A621

Effective date: 20211126

A977 Report on retrieval

Free format text: JAPANESE INTERMEDIATE CODE: A971007

Effective date: 20221031

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20221101

A601 Written request for extension of time

Free format text: JAPANESE INTERMEDIATE CODE: A601

Effective date: 20230201

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20230324

A131 Notification of reasons for refusal

Free format text: JAPANESE INTERMEDIATE CODE: A131

Effective date: 20230623

A521 Request for written amendment filed

Free format text: JAPANESE INTERMEDIATE CODE: A523

Effective date: 20230920

TRDD Decision of grant or rejection written
A01 Written decision to grant a patent or to grant a registration (utility model)

Free format text: JAPANESE INTERMEDIATE CODE: A01

Effective date: 20231109

A61 First payment of annual fees (during grant procedure)

Free format text: JAPANESE INTERMEDIATE CODE: A61

Effective date: 20231208

R150 Certificate of patent or registration of utility model

Ref document number: 7402159

Country of ref document: JP

Free format text: JAPANESE INTERMEDIATE CODE: R150

RD04 Notification of resignation of power of attorney

Free format text: JAPANESE INTERMEDIATE CODE: R3D04

RD02 Notification of acceptance of power of attorney

Free format text: JAPANESE INTERMEDIATE CODE: R3D02