CA3204314A1 - Sars-cov-2 mpro inhibitor compounds - Google Patents

Sars-cov-2 mpro inhibitor compounds

Info

Publication number
CA3204314A1
CA3204314A1 CA3204314A CA3204314A CA3204314A1 CA 3204314 A1 CA3204314 A1 CA 3204314A1 CA 3204314 A CA3204314 A CA 3204314A CA 3204314 A CA3204314 A CA 3204314A CA 3204314 A1 CA3204314 A1 CA 3204314A1
Authority
CA
Canada
Prior art keywords
oxopyrrolidin
butan
dioxo
cyclopropylamino
dimethylpentanamide
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
CA3204314A
Other languages
English (en)
French (fr)
Inventor
Miles Stuart Congreve
John Andrew Christopher
Mark PICKWORTH
Chris DE GRAAF
Alicia Perez HIGUERUELO
Jonathan Stephen Mason
Santosh S. Kulkarni
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.)
Nxera Pharma UK Ltd
Original Assignee
Heptares Therapeutics Ltd
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
Priority claimed from GBGB2020190.1A external-priority patent/GB202020190D0/en
Priority claimed from GBGB2107385.3A external-priority patent/GB202107385D0/en
Application filed by Heptares Therapeutics Ltd filed Critical Heptares Therapeutics Ltd
Publication of CA3204314A1 publication Critical patent/CA3204314A1/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
    • C07D207/24—Oxygen or sulfur atoms
    • C07D207/26—2-Pyrrolidones
    • C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
    • C07D207/267—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to the ring nitrogen atom
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • C07D403/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
    • C07F9/572—Five-membered 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
    • C07K5/04—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
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Virology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Oncology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Biochemistry (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyrrole Compounds (AREA)
CA3204314A 2020-12-18 2021-12-20 Sars-cov-2 mpro inhibitor compounds Pending CA3204314A1 (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
GB2020190.1 2020-12-18
GBGB2020190.1A GB202020190D0 (en) 2020-12-18 2020-12-18 Sars-Cov-2 MPRO inhibitor compounds
GBGB2107385.3A GB202107385D0 (en) 2021-05-24 2021-05-24 Sars-cov-2 mpro inhibitor compounds
GB2107385.3 2021-05-24
PCT/GB2021/053374 WO2022129953A1 (en) 2020-12-18 2021-12-20 Sars-cov-2 mpro inhibitor compounds

Publications (1)

Publication Number Publication Date
CA3204314A1 true CA3204314A1 (en) 2022-06-23

Family

ID=79282959

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3204314A Pending CA3204314A1 (en) 2020-12-18 2021-12-20 Sars-cov-2 mpro inhibitor compounds

Country Status (8)

Country Link
US (1) US20240083845A1 (cg-RX-API-DMAC7.html)
EP (1) EP4263502B1 (cg-RX-API-DMAC7.html)
JP (1) JP2024500136A (cg-RX-API-DMAC7.html)
KR (1) KR20230121780A (cg-RX-API-DMAC7.html)
AU (1) AU2021402179A1 (cg-RX-API-DMAC7.html)
CA (1) CA3204314A1 (cg-RX-API-DMAC7.html)
IL (1) IL303757A (cg-RX-API-DMAC7.html)
WO (1) WO2022129953A1 (cg-RX-API-DMAC7.html)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP4545075A1 (en) * 2022-06-23 2025-04-30 Goryo Chemical, Inc. Calpain inhibitor
CN115073347B (zh) * 2022-07-14 2024-07-30 浙江江北药业有限公司 一种内酰胺环类医药中间体的制备方法
WO2024102455A1 (en) * 2022-11-09 2024-05-16 Emory University Non-covalent inhibitors of coronavirus main protease
CN116535460A (zh) * 2023-04-28 2023-08-04 中国人民解放军军事科学院军事医学研究院 一类含硫拟肽类化合物及其制备方法和用途

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5763576A (en) * 1995-10-06 1998-06-09 Georgia Tech Research Corp. Tetrapeptide α-ketoamides
SK6572000A3 (en) * 1997-11-05 2000-10-09 Novartis Ag Dipeptide nitriles, process for the preparation thereof, their use as medicaments and pharmaceutical composition comprising them
WO2004093860A1 (en) * 2003-04-21 2004-11-04 Pfizer Inc. Inhibitors of sars related coronavirus proteinase
WO2005113580A1 (en) * 2004-05-21 2005-12-01 Pfizer Inc. Anticoronviral compounds and compositions, their pharmaceutical uses and materials for their synthesis
CN100363346C (zh) * 2004-10-22 2008-01-23 清华大学 冠状病毒主蛋白酶的小分子抑制剂、制备方法及其应用
WO2006061714A2 (en) * 2004-12-09 2006-06-15 Pfizer Inc. Anticoronaviral compounds and compositions, their pharmaceutical uses and materials for their synthesis
CA2850003C (en) * 2011-09-27 2020-01-07 Kansas State University Research Foundation Broad-spectrum antivirals against 3c or 3c-like proteases of picornavirus-like supercluster: picornaviruses, caliciviruses and coronaviruses
CN103130710B (zh) * 2011-11-29 2015-12-16 南开大学 抗肠病毒71(ev71)己内酰胺醛类化合物及其制备方法和用途
CN103145608B (zh) * 2011-12-07 2015-09-02 南开大学 抗肠病毒71(ev71)己内酰胺类化合物及其制备方法和用途
TW201817714A (zh) * 2016-08-30 2018-05-16 英商葛蘭素史密斯克藍智慧財產權有限公司 抑制3c及3cl蛋白酶之化合物及其使用方法
CN110818691A (zh) * 2018-08-09 2020-02-21 中国科学院上海药物研究所 酮酰胺类化合物及其制备方法、药物组合物和用途

Also Published As

Publication number Publication date
EP4263502C0 (en) 2024-12-25
US20240083845A1 (en) 2024-03-14
IL303757A (en) 2023-08-01
EP4263502A1 (en) 2023-10-25
KR20230121780A (ko) 2023-08-21
WO2022129953A1 (en) 2022-06-23
JP2024500136A (ja) 2024-01-04
AU2021402179A9 (en) 2024-09-26
AU2021402179A1 (en) 2023-07-06
EP4263502B1 (en) 2024-12-25

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