AU2021381437C1 - Novel spiropyrrolidine derived antiviral agents - Google Patents

Novel spiropyrrolidine derived antiviral agents

Info

Publication number
AU2021381437C1
AU2021381437C1 AU2021381437A AU2021381437A AU2021381437C1 AU 2021381437 C1 AU2021381437 C1 AU 2021381437C1 AU 2021381437 A AU2021381437 A AU 2021381437A AU 2021381437 A AU2021381437 A AU 2021381437A AU 2021381437 C1 AU2021381437 C1 AU 2021381437C1
Authority
AU
Australia
Prior art keywords
optionally substituted
compound
mmol
alkyl
acetone
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
AU2021381437A
Other languages
English (en)
Other versions
AU2021381437A9 (en
AU2021381437B2 (en
AU2021381437A1 (en
Inventor
Samuel Bartlett
Hui Cao
Xuri Gao
Yong He
Nathaniel Thomas KENTON
Wei Li
Jiang Long
Jun Ma
Yat Sun Or
Joseph D. PANARESE
Xiaowen Peng
Ruichao Shen
Guoqiang Wang
Xuechao Xing
Jiajun Zhang
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.)
Enanta Pharmaceuticals Inc
Original Assignee
Enanta Pharmaceuticals 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
Priority claimed from US17/479,244 external-priority patent/US11384090B2/en
Priority claimed from US17/479,530 external-priority patent/US11352363B1/en
Application filed by Enanta Pharmaceuticals Inc filed Critical Enanta Pharmaceuticals Inc
Publication of AU2021381437A1 publication Critical patent/AU2021381437A1/en
Publication of AU2021381437A9 publication Critical patent/AU2021381437A9/en
Publication of AU2021381437B2 publication Critical patent/AU2021381437B2/en
Application granted granted Critical
Publication of AU2021381437C1 publication Critical patent/AU2021381437C1/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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
    • 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
    • A61K31/407—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 condensed with other heterocyclic ring systems, e.g. ketorolac, physostigmine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/06—Antiasthmatics
    • 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
    • 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
    • C07D471/12—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 three hetero rings
    • C07D471/20—Spiro-condensed systems
    • 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
    • C07D487/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—Ortho-condensed systems
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Virology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Molecular Biology (AREA)
  • Pulmonology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
AU2021381437A 2020-11-23 2021-11-22 Novel spiropyrrolidine derived antiviral agents Active AU2021381437C1 (en)

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
US202063117170P 2020-11-23 2020-11-23
US63/117,170 2020-11-23
US202163142663P 2021-01-28 2021-01-28
US63/142,663 2021-01-28
US17/479,244 US11384090B2 (en) 2020-11-23 2021-09-20 Spiropyrrolidine derived antiviral agents
US17/479,530 US11352363B1 (en) 2020-11-23 2021-09-20 Spiropyrrolidine derived antiviral agents
US17/479,244 2021-09-20
US17/479,530 2021-09-20
PCT/US2021/060247 WO2022109363A1 (en) 2020-11-23 2021-11-22 Novel spiropyrrolidine derived antiviral agents

Publications (4)

Publication Number Publication Date
AU2021381437A1 AU2021381437A1 (en) 2023-06-22
AU2021381437A9 AU2021381437A9 (en) 2024-10-10
AU2021381437B2 AU2021381437B2 (en) 2025-12-18
AU2021381437C1 true AU2021381437C1 (en) 2026-04-02

Family

ID=78725298

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2021381437A Active AU2021381437C1 (en) 2020-11-23 2021-11-22 Novel spiropyrrolidine derived antiviral agents

Country Status (13)

Country Link
EP (1) EP4001279A1 (cg-RX-API-DMAC10.html)
JP (1) JP7875859B2 (cg-RX-API-DMAC10.html)
KR (1) KR20230124582A (cg-RX-API-DMAC10.html)
CN (1) CN114524821B (cg-RX-API-DMAC10.html)
AU (1) AU2021381437C1 (cg-RX-API-DMAC10.html)
CA (1) CA3173333A1 (cg-RX-API-DMAC10.html)
CL (1) CL2023001476A1 (cg-RX-API-DMAC10.html)
CO (1) CO2023008018A2 (cg-RX-API-DMAC10.html)
IL (1) IL302991A (cg-RX-API-DMAC10.html)
MX (1) MX2023005984A (cg-RX-API-DMAC10.html)
TW (1) TW202237616A (cg-RX-API-DMAC10.html)
UY (1) UY39529A (cg-RX-API-DMAC10.html)
WO (1) WO2022109363A1 (cg-RX-API-DMAC10.html)

Families Citing this family (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US12540141B2 (en) 2020-11-23 2026-02-03 Enanta Pharmaceuticals, Inc. Spiropyrrolidine derived antiviral agents
WO2022109360A1 (en) 2020-11-23 2022-05-27 Enanta Pharmaceuticals, Inc. Novel spiropyrrolidine derived antiviral agents
US11970502B2 (en) 2021-05-04 2024-04-30 Enanta Pharmaceuticals, Inc. Macrocyclic antiviral agents
US12398147B2 (en) 2021-05-11 2025-08-26 Enanta Pharmaceuticals, Inc. Macrocyclic spiropyrrolidine derived antiviral agents
WO2023283256A1 (en) 2021-07-09 2023-01-12 Aligos Therapeutics, Inc. Anti-viral compounds
US12643905B2 (en) 2021-07-23 2026-06-02 Enanta Pharmaceuticals, Inc. Spiropyrrolidine derived antiviral agents
US12479854B2 (en) 2021-07-29 2025-11-25 Enanta Pharmaceuticals, Inc. Spiropyrrolidine derived antiviral agents
US11858945B2 (en) 2021-11-12 2024-01-02 Enanta Pharmaceuticals, Inc. Alkyne-containing antiviral agents
WO2023086352A1 (en) 2021-11-12 2023-05-19 Enanta Pharmaceuticals, Inc. Novel spiropyrrolidine derived antiviral agents
WO2023086400A1 (en) 2021-11-12 2023-05-19 Enanta Pharmaceuticals, Inc. Novel spiropyrrolidine derived antiviral agents
US11993600B2 (en) 2021-12-08 2024-05-28 Enanta Pharmaceuticals, Inc. Saturated spirocyclics as antiviral agents
CN117751124B (zh) * 2021-12-17 2026-07-24 南京药石科技股份有限公司 螺环氧化吲哚类化合物及其用于制备抗病毒蛋白酶抑制剂药物的用途
US12006291B2 (en) 2022-01-11 2024-06-11 Enanta Pharmaceuticals, Inc. Processes for the preparation of 4,6,7-trifluoro-1H-indole-2-carboxylic acid
CA3254409A1 (en) * 2022-03-18 2023-09-21 Enanta Pharmaceuticals, Inc. PROCESSES FOR PREPARING SUBSTITUTED SPIROOXINDOLE DERIVATIVES
US12145942B2 (en) 2022-04-05 2024-11-19 Enanta Pharmaceuticals, Inc. Spiropyrrolidine derived antiviral agents
AU2023303408A1 (en) 2022-07-06 2024-12-19 Aligos Therapeutics, Inc. Anti-viral compounds
CN116621918B (zh) * 2022-07-20 2023-10-31 深圳信立泰药业股份有限公司 一种螺环化合物及其制备方法与应用
CN115466189B (zh) * 2022-09-19 2024-08-30 安徽普利药业有限公司 一种氨基酸及其衍生物的纯化方法
IL320050A (en) * 2022-10-06 2025-06-01 Enanta Pharm Inc Crystalline forms of SARS-anti-COV-2 compound
CN115894504A (zh) * 2022-10-21 2023-04-04 深圳信立泰药业股份有限公司 一种冠状病毒3cl蛋白酶抑制剂及其用途
EP4612156A1 (en) * 2022-11-02 2025-09-10 Aligos Therapeutics, Inc. Anti-viral compounds
WO2024094152A1 (zh) * 2022-11-03 2024-05-10 中国科学院上海药物研究所 一类螺环化合物、其制备方法及用途
CN118852175A (zh) * 2023-01-17 2024-10-29 深圳信立泰药业股份有限公司 一种螺环化合物晶型及其制备方法与应用
CN119139307B (zh) * 2023-12-29 2025-09-23 上海柯君医药科技有限公司 螺环类化合物在制备3CLpro蛋白酶抑制剂或药物中的用途
CN119930495A (zh) * 2025-01-22 2025-05-06 中国科学技术大学先进技术研究院 化合物及其制备方法
CN120815076A (zh) * 2025-07-28 2025-10-21 广州医科大学附属第一医院(广州呼吸中心) Sal-0133在制备预防和/或治疗人鼻病毒感染的药物中的应用

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017222935A1 (en) * 2016-06-20 2017-12-28 Kansas State University Research Foundation Small molecule therapeutic inhibitors against picornaviruses, caliciviruses, and coronaviruses
WO2018042343A2 (en) * 2016-08-30 2018-03-08 Glaxosmithkline Intellectual Property (No.2) Limited Compounds that inhibit 3c and 3cl proteases and methods of use thereof

Family Cites Families (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5508269A (en) 1994-10-19 1996-04-16 Pathogenesis Corporation Aminoglycoside formulation for aerosolization
US6083922A (en) 1996-04-02 2000-07-04 Pathogenesis, Corp. Method and a tobramycin aerosol formulation for treatment prevention and containment of tuberculosis
US5767068A (en) 1997-02-13 1998-06-16 Pathogenesis Corporation Pure biologically active colistin, its components and a colistin formulation for treatment of pulmonary infections
US7504382B2 (en) 2003-05-06 2009-03-17 Cytovia, Inc. Protease inhibitors for coronaviruses and SARS-CoV and the use thereof
DE602004011047T2 (de) 2003-05-13 2008-12-24 Universität Zu Lübeck Kristallstruktur von der humanen coronavirus 229e hauptproteinase und deren verwendung zur entwicklung von sars-inhibitoren
US20060014821A1 (en) 2003-08-27 2006-01-19 Agouron Pharmaceuticals, Inc. Inhibitors of SARS 3C like protease
US7462594B2 (en) 2003-12-31 2008-12-09 Taigen Biotechnology Co., Ltd. Peptide-like compounds that inhibit coronaviral 3CL and flaviviridae viral proteases
WO2005113580A1 (en) 2004-05-21 2005-12-01 Pfizer Inc. Anticoronviral compounds and compositions, their pharmaceutical uses and materials for their synthesis
WO2006061714A2 (en) 2004-12-09 2006-06-15 Pfizer Inc. Anticoronaviral compounds and compositions, their pharmaceutical uses and materials for their synthesis
PE20121506A1 (es) * 2006-07-14 2012-11-26 Amgen Inc Compuestos triazolopiridinas como inhibidores de c-met
MY160077A (en) * 2011-01-21 2017-02-15 Univ Sains Malaysia Curcumin compounds and their preparations thereof
UY34094A (es) * 2011-05-27 2013-01-03 Novartis Ag Derivados de la piperidina 3-espirocíclica como agonistas de receptores de la ghrelina
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
CA2859915A1 (en) * 2012-01-03 2013-07-11 Ruey J. Yu N-acylpeptide derivatives and their uses
CA2872147A1 (en) 2012-05-02 2013-11-07 Kansas State University Research Foundation Macrocyclic and peptidomimetic compounds as broad-spectrum antivirals against 3c or 3c-like proteases of picornaviruses, caliciviruses and coronaviruses
WO2017035409A1 (en) * 2015-08-26 2017-03-02 Achillion Pharmaceuticals, Inc. Aryl, heteroaryl, and heterocyclic compounds for treatment of immune and inflammatory disorders
WO2018023054A1 (en) 2016-07-28 2018-02-01 Kansas State University Research Foundation Protease transition state inhibitor prodrugs
JP7691691B2 (ja) * 2020-09-11 2025-06-12 公立大学法人横浜市立大学 新型コロナウイルス感染症の予防又は治療用の食品組成物、医薬品組成物、医薬部外品組成物、化粧品組成物、及び雑貨
WO2022109360A1 (en) * 2020-11-23 2022-05-27 Enanta Pharmaceuticals, Inc. Novel spiropyrrolidine derived antiviral agents

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2017222935A1 (en) * 2016-06-20 2017-12-28 Kansas State University Research Foundation Small molecule therapeutic inhibitors against picornaviruses, caliciviruses, and coronaviruses
WO2018042343A2 (en) * 2016-08-30 2018-03-08 Glaxosmithkline Intellectual Property (No.2) Limited Compounds that inhibit 3c and 3cl proteases and methods of use thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
Thanigaimalai, ., et al. "Design, synthesis, and biological evaluation of novel dipeptide-type SARS-CoV 3CL protease inhibitors: Structure-activity relationship study." European Journal of Medicinal Chemistry, 2013, 65, p 436-447 *

Also Published As

Publication number Publication date
AU2021381437A9 (en) 2024-10-10
JP7875859B2 (ja) 2026-06-18
IL302991A (en) 2023-07-01
CN114524821B (zh) 2026-01-02
CA3173333A1 (en) 2022-05-27
TW202237616A (zh) 2022-10-01
CN114524821A (zh) 2022-05-24
JP2023551174A (ja) 2023-12-07
EP4001279A1 (en) 2022-05-25
CO2023008018A2 (es) 2023-07-10
AU2021381437B2 (en) 2025-12-18
KR20230124582A (ko) 2023-08-25
UY39529A (es) 2022-06-30
MX2023005984A (es) 2023-08-17
CL2023001476A1 (es) 2023-12-11
WO2022109363A1 (en) 2022-05-27
AU2021381437A1 (en) 2023-06-22

Similar Documents

Publication Publication Date Title
AU2021381437B2 (en) Novel spiropyrrolidine derived antiviral agents
US12540141B2 (en) Spiropyrrolidine derived antiviral agents
ES2936277B2 (es) Peptidos funcionalizados como agentes antivirales
US11352363B1 (en) Spiropyrrolidine derived antiviral agents
US11384090B2 (en) Spiropyrrolidine derived antiviral agents
US12479854B2 (en) Spiropyrrolidine derived antiviral agents
US11339170B1 (en) Spiropyrrolidine derived antiviral agents
WO2022235605A1 (en) Novel macrocyclic antiviral agents
WO2023091561A1 (en) Novel spiropyrrolidine derived antiviral agents
IL300589A (en) Peptides that function as antiviral agents
US20230115107A1 (en) Novel spiropyrrolidine derived antiviral agents
JP2022506337A (ja) B型肝炎ウイルス(hbv)に対して活性を有する6,7-ジヒドロ-4h-ピラゾロ[1,5-a]ピラジンインドール-2-カルボキサミド
KR20240044452A (ko) 신규한 스피로피롤리딘 유래 항바이러스제
KR20180021820A (ko) Ido 억제제
JP2022512870A (ja) B型肝炎ウイルス(hbv)に対して活性を有する新規尿素6,7-ジヒドロ-4h-ピラゾロ[1,5-a]ピラジン
WO2023003610A1 (en) Novel spiropyrrolidine derived antiviral agents
JP2022512873A (ja) B型肝炎ウイルス(hbv)に対して活性を有する新規尿素6,7-ジヒドロ-4h-ピラゾロ[4,3-c]ピリジン
HK40071048A (en) Novel spiropyrrolidine derived antiviral agents
EA048496B1 (ru) Новые противовирусные агенты на основе производных спиропирролидина
HK40096316A (en) Functionalized peptides as antiviral agents

Legal Events

Date Code Title Description
SREP Specification republished
DA2 Applications for amendment section 104

Free format text: THE NATURE OF THE AMENDMENT IS AS SHOWN IN THE STATEMENT(S) FILED 18 DEC 2025

DA3 Amendments made section 104

Free format text: THE NATURE OF THE AMENDMENT IS AS SHOWN IN THE STATEMENT(S) FILED 18 DEC 2025

FGA Letters patent sealed or granted (standard patent)