CA2699989C - N-phenyl-dioxo-hydro pyrimidines useful as hepatitis c virus (hcv) inhibitor - Google Patents

N-phenyl-dioxo-hydro pyrimidines useful as hepatitis c virus (hcv) inhibitor Download PDF

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Publication number
CA2699989C
CA2699989C CA2699989A CA2699989A CA2699989C CA 2699989 C CA2699989 C CA 2699989C CA 2699989 A CA2699989 A CA 2699989A CA 2699989 A CA2699989 A CA 2699989A CA 2699989 C CA2699989 C CA 2699989C
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CA
Canada
Prior art keywords
phenyl
tert
butyl
dioxo
methanesulfonamide
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.)
Expired - Fee Related
Application number
CA2699989A
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English (en)
French (fr)
Other versions
CA2699989A1 (en
Inventor
Pamela L. Donner
John T. Randolph
Allan C. Krueger
David A. Betebenner
Douglas K. Hutchinson
Dachun Liu
Yaya Liu
Kenton L. Longenecker
Clarence J. Maring
John K. Pratt
Todd W. Rockway
Kent D. Stewart
Rolf Wagner
David M. Barnes
Shuang Chen
Thaddeus S. Ii Franczyk
Yi Gao
Anthony R. Haight
John E. Hengeveld
Rodger F. Henry
Brian J. Kotecki
Xiaochun Lou
Geoff G. Z. Zhang
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AbbVie Bahamas Ltd
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AbbVie Bahamas Ltd
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Publication of CA2699989A1 publication Critical patent/CA2699989A1/en
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Publication of CA2699989C publication Critical patent/CA2699989C/en
Expired - Fee Related legal-status Critical Current
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/20—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D239/22—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to ring carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
    • 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
    • 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
    • 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
    • A61P31/20—Antivirals for DNA viruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52—Two oxygen atoms
    • C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • C07D239/545—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/553—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals with other hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms with halogen atoms or nitro radicals directly attached to ring carbon atoms, e.g. fluorouracil
    • 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
    • C07D401/10—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 carbon chain containing aromatic rings
    • 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
    • C07D403/10—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 aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
    • 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
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/513—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
    • 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
    • C07B2200/13—Crystalline forms, e.g. polymorphs

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Virology (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Biotechnology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CA2699989A 2007-09-17 2008-09-17 N-phenyl-dioxo-hydro pyrimidines useful as hepatitis c virus (hcv) inhibitor Expired - Fee Related CA2699989C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US97288707P 2007-09-17 2007-09-17
US60/972,887 2007-09-17
US9679408P 2008-09-13 2008-09-13
US61/096,794 2008-09-13
PCT/US2008/076594 WO2009039135A1 (en) 2007-09-17 2008-09-17 N-phenyl-dioxo-hydropyrimidines useful as hepatitis c virus (hcv) inhibitors

Publications (2)

Publication Number Publication Date
CA2699989A1 CA2699989A1 (en) 2009-03-26
CA2699989C true CA2699989C (en) 2014-03-25

Family

ID=40091991

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2699989A Expired - Fee Related CA2699989C (en) 2007-09-17 2008-09-17 N-phenyl-dioxo-hydro pyrimidines useful as hepatitis c virus (hcv) inhibitor

Country Status (14)

Country Link
US (2) US8178548B2 (en:Method)
EP (3) EP2377854A1 (en:Method)
JP (1) JP5726527B2 (en:Method)
CN (3) CN105294569A (en:Method)
AT (1) ATE512954T1 (en:Method)
CA (1) CA2699989C (en:Method)
DK (1) DK2203430T3 (en:Method)
HR (1) HRP20110632T1 (en:Method)
MX (1) MX2010002904A (en:Method)
PL (1) PL2203430T3 (en:Method)
PT (1) PT2203430E (en:Method)
RU (1) RU2542099C2 (en:Method)
WO (1) WO2009039135A1 (en:Method)
ZA (1) ZA201002690B (en:Method)

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MX2010002904A (es) * 2007-09-17 2010-06-02 Abbott Lab N-fenil-dioxo-hidropirimidinas utiles como inhibidores de virus de hepatitis c (hcv).
KR101552474B1 (ko) * 2007-09-17 2015-09-11 애브비 바하마스 리미티드 Ｃ형 간염 치료용 우라실 또는 티민 유도체
EP2639226B1 (en) 2007-09-17 2016-08-31 AbbVie Bahamas Ltd. Anti-infective pyrimidines and uses thereof
CN102099335A (zh) 2008-07-23 2011-06-15 弗·哈夫曼-拉罗切有限公司 杂环抗病毒化合物
JP2012503620A (ja) 2008-09-26 2012-02-09 エフ．ホフマン−ラ ロシュ アーゲー Ｈｃｖを処置するためのピリンまたはピラジン誘導体
AU2009309813A1 (en) 2008-10-30 2010-05-06 F. Hoffmann-La Roche Ag Heterocyclic antiviral arylpyridone derivatives
BRPI0924121A2 (pt) 2008-12-22 2019-09-24 Hoffmann La Roche compostos antivirais heterocíclicos
BRPI1016266A2 (pt) 2009-03-06 2019-09-24 Hoffmann La Roche compostos antivirais heterocíclicos
JP5744003B2 (ja) * 2009-03-24 2015-07-01 アッヴィ・バハマズ・リミテッド 抗ウイルス化合物を調製する方法
AU2010240888A1 (en) * 2009-04-25 2011-11-17 F. Hoffmann-La Roche Ag Heterocyclic antiviral compounds
TWI428332B (zh) 2009-06-09 2014-03-01 Hoffmann La Roche 雜環抗病毒化合物
AU2010264802A1 (en) * 2009-06-24 2012-01-19 F. Hoffmann-La Roche Ag Heterocyclic antiviral compound
BR112012005616A2 (pt) 2009-09-21 2016-06-21 Hoffmann La Roche compostos antivirais heterocíclicos
US8822496B2 (en) 2009-10-30 2014-09-02 Boehringer Ingelheim International Gmbh Dosage regimens for HCV combination therapy
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US8841487B2 (en) 2010-07-16 2014-09-23 Abbvie Inc. Phosphine ligands for catalytic reactions
US8975443B2 (en) 2010-07-16 2015-03-10 Abbvie Inc. Phosphine ligands for catalytic reactions
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CN106065009B (zh) * 2014-06-28 2019-03-01 广东东阳光药业有限公司 作为丙型肝炎抑制剂的化合物及其在药物中的应用
US11192914B2 (en) 2016-04-28 2021-12-07 Emory University Alkyne containing nucleotide and nucleoside therapeutic compositions and uses related thereto
US11026958B2 (en) 2016-11-01 2021-06-08 Merck Sharp & Dohme Corp. Substituted 6-membered aryl or heteroaryl allosteric modulators of nicotinic acetylcholine receptors
JP7252973B2 (ja) 2018-03-26 2023-04-05 ノバルティス アーゲー Ｎ－（３－（７Ｈ－ピロロ［２，３－ｄ］ピリミジン－４－イル）フェニル）ベンズアミド誘導体
CN110483496B (zh) * 2019-07-17 2021-05-04 杭州市西溪医院 一类具有尿嘧啶-苯并噻唑结构衍生物、其制备方法及抗hcv药物的应用
US20220387602A1 (en) * 2019-09-16 2022-12-08 Novartis Ag Bifunctional degraders and their methods of use
CN114424227B (zh) 2019-09-16 2025-10-21 维萨国际服务协会 用于验证卡图像的系统、方法和计算机程序产品
EP3819006A1 (en) 2019-11-05 2021-05-12 Technische Universität Dresden Compounds with thymine skeleton for use in medicine
CN111018910A (zh) * 2019-12-05 2020-04-17 上海应用技术大学 一种铜催化合成含芳环α-羟基膦酸酯的方法
CN111518036A (zh) * 2020-04-29 2020-08-11 杭州勇诚睿生物科技有限公司 一种达沙布韦关键中间体的制备方法
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KR101552474B1 (ko) 2007-09-17 2015-09-11 애브비 바하마스 리미티드 Ｃ형 간염 치료용 우라실 또는 티민 유도체
CN102099335A (zh) 2008-07-23 2011-06-15 弗·哈夫曼-拉罗切有限公司 杂环抗病毒化合物

Also Published As

Publication number Publication date
HK1145839A1 (en) 2011-05-06
RU2542099C2 (ru) 2015-02-20
US8178548B2 (en) 2012-05-15
HRP20110632T1 (hr) 2011-10-31
EP2203430B1 (en) 2011-06-15
JP5726527B2 (ja) 2015-06-03
US20120189580A1 (en) 2012-07-26
CN105693626A (zh) 2016-06-22
CN101918369B (zh) 2016-02-24
MX2010002904A (es) 2010-06-02
CA2699989A1 (en) 2009-03-26
US20090176784A1 (en) 2009-07-09
ZA201002690B (en) 2015-12-23
RU2010114826A (ru) 2011-10-27
WO2009039135A1 (en) 2009-03-26
ATE512954T1 (de) 2011-07-15
EP2377854A1 (en) 2011-10-19
US8986740B2 (en) 2015-03-24
JP2010539188A (ja) 2010-12-16
CN105294569A (zh) 2016-02-03
CN101918369A (zh) 2010-12-15
DK2203430T3 (da) 2011-09-26
PT2203430E (pt) 2011-09-02
PL2203430T3 (pl) 2011-12-30
EP2203430A1 (en) 2010-07-07
EP2548873A1 (en) 2013-01-23

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