EA201171406A1 - Спирооксетановые производные урацилсодержащих нуклеозидов - Google Patents

Спирооксетановые производные урацилсодержащих нуклеозидов

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Publication number
EA201171406A1
EA201171406A1 EA201171406A EA201171406A EA201171406A1 EA 201171406 A1 EA201171406 A1 EA 201171406A1 EA 201171406 A EA201171406 A EA 201171406A EA 201171406 A EA201171406 A EA 201171406A EA 201171406 A1 EA201171406 A1 EA 201171406A1
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EA
Eurasian Patent Office
Prior art keywords
phenyl
6alkyl
optionally substituted
formula
spirooxetane
Prior art date
Application number
EA201171406A
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English (en)
Other versions
EA022084B1 (ru
Inventor
Тим Хьюго Мария Йонкерс
Пьер Жан-Мари Бернар Рабуассон
Коэн Вандик
Стивен Морис Паула Ван Хоф
Лили Ху
Абделлах Тахри
Original Assignee
ЯНССЕН ПРОДАКТС, Эл.Пи.
Медивир Аб
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.)
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Publication date
Application filed by ЯНССЕН ПРОДАКТС, Эл.Пи., Медивир Аб filed Critical ЯНССЕН ПРОДАКТС, Эл.Пи.
Publication of EA201171406A1 publication Critical patent/EA201171406A1/ru
Publication of EA022084B1 publication Critical patent/EA022084B1/ru

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/067—Pyrimidine radicals with ribosyl as the saccharide radical
    • 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
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/503—Pyridazines; Hydrogenated pyridazines spiro-condensed
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
    • A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
    • A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
    • A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
    • A61K31/7068—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid
    • A61K31/7072—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines having oxo groups directly attached to the pyrimidine ring, e.g. cytidine, cytidylic acid having two oxo groups directly attached to the pyrimidine ring, e.g. uridine, uridylic acid, thymidine, zidovudine
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/18—Acyclic radicals, substituted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/06—Pyrimidine radicals
    • C07H19/10—Pyrimidine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
    • C07H21/02—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids with ribosyl as saccharide radical

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Virology (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Communicable Diseases (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)

Abstract

Раскрыты соединения формулы (I), включая их любые возможные стереоизомеры, где Rпредставляет собой монофосфатную, дифосфатную или трифосфатную сложноэфирную группу; или Rпредставляет собой формулу (II) или формулу (III), Rпредставляет собой необязательно замещенный фенил, необязательно замещенный нафтил или необязательно замещенный индолил; Rи R' представляют собой водород, C-Салкил, бензил или фенил; или Rи R' образуют С-Сциклоалкил; Rпредставляет собой C-Салкил, С-Сциклоалкил, фенил или фенил-C-Салкил, где фенильный фрагмент в фениле или фенил-С-Салкиле необязательно замещен; или их фармацевтически приемлемая соль или сольват; технологии получения лекарственных средств и применение соединений I в качестве ингибиторов вируса HCV.
EA201171406A 2009-05-14 2010-05-11 Спирооксетановые производные урацилсодержащих нуклеозидов EA022084B1 (ru)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP09160215 2009-05-14
PCT/EP2010/056438 WO2010130726A1 (en) 2009-05-14 2010-05-11 Uracyl spirooxetane nucleosides

Publications (2)

Publication Number Publication Date
EA201171406A1 true EA201171406A1 (ru) 2012-05-30
EA022084B1 EA022084B1 (ru) 2015-10-30

Family

ID=40823307

Family Applications (1)

Application Number Title Priority Date Filing Date
EA201171406A EA022084B1 (ru) 2009-05-14 2010-05-11 Спирооксетановые производные урацилсодержащих нуклеозидов

Country Status (39)

Country Link
US (2) US8481510B2 (ru)
EP (2) EP2511282B1 (ru)
JP (2) JP5778135B2 (ru)
KR (1) KR101806837B1 (ru)
CN (1) CN102439024B (ru)
AP (1) AP2783A (ru)
AR (1) AR076579A1 (ru)
AU (1) AU2010247439B2 (ru)
BR (1) BRPI1010579A2 (ru)
CA (1) CA2760329C (ru)
CL (1) CL2011002859A1 (ru)
CO (1) CO6440533A2 (ru)
CR (1) CR20120297A (ru)
CY (2) CY1114081T1 (ru)
DK (2) DK2511282T3 (ru)
EA (1) EA022084B1 (ru)
EC (1) ECSP11011461A (ru)
ES (2) ES2411086T3 (ru)
HK (1) HK1166326A1 (ru)
HN (1) HN2011003014A (ru)
HR (2) HRP20130554T1 (ru)
IL (1) IL215955A (ru)
JO (1) JO3027B1 (ru)
ME (1) ME01478B (ru)
MX (1) MX2011012027A (ru)
MY (1) MY157018A (ru)
NI (1) NI201100197A (ru)
NZ (1) NZ596073A (ru)
PL (2) PL2430035T3 (ru)
PT (2) PT2430035E (ru)
RS (1) RS52822B (ru)
SG (1) SG175981A1 (ru)
SI (2) SI2511282T1 (ru)
SM (2) SMT201300078B (ru)
TW (1) TWI461432B (ru)
UA (1) UA105790C2 (ru)
UY (1) UY32642A (ru)
WO (1) WO2010130726A1 (ru)
ZA (1) ZA201108309B (ru)

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US8173621B2 (en) 2008-06-11 2012-05-08 Gilead Pharmasset Llc Nucleoside cyclicphosphates
TW201031675A (en) 2008-12-23 2010-09-01 Pharmasset Inc Synthesis of purine nucleosides
JO3027B1 (ar) 2009-05-14 2016-09-05 Janssen Products Lp نيوكليوسيدات يوراسيل سبيرواوكسيتان
PT2638054E (pt) 2010-11-10 2015-03-02 Medivir Ab Fosforamidatos de nucleósidos de uracilo espirooxetano
WO2012062869A1 (en) * 2010-11-10 2012-05-18 Janssen Products, Lp Uracyl spirooxetane nucleoside phosphoramidates
US8841275B2 (en) * 2010-11-30 2014-09-23 Gilead Pharmasset Llc 2′-spiro-nucleosides and derivatives thereof useful for treating hepatitis C virus and dengue virus infections
AU2015252113B2 (en) * 2010-11-30 2017-05-04 Gilead Pharmasset Llc Compounds
AU2012242517B2 (en) * 2011-04-13 2016-12-15 Gilead Sciences, Inc. 1'-substituted pyrimidine N-nucleoside analogs for antiviral treatment
AU2012358804B2 (en) * 2011-12-22 2018-04-19 Alios Biopharma, Inc. Substituted phosphorothioate nucleotide analogs
EP2861611B1 (en) 2012-05-25 2016-07-13 Janssen Sciences Ireland UC Uracyl spirooxetane nucleosides
KR101857337B1 (ko) * 2013-03-08 2018-05-11 난징 산홈 팔마세우티칼 컴퍼니 리미티드 신규한 뉴클레오시드 포스포라미데이트 화합물 및 이의 용도
WO2014169280A2 (en) 2013-04-12 2014-10-16 Achillion Pharmaceuticals, Inc. Deuterated nucleoside prodrugs useful for treating hcv
CN104231023B (zh) * 2013-06-06 2019-02-05 南京汇诚制药有限公司 三环稠杂环类核苷氨基磷酸酯化合物、其制备方法及应用
EP3074412A4 (en) * 2013-11-28 2017-05-31 Janssen Sciences Ireland UC Crystal form of nucleoside inhibitor of hcv
CA2978085C (en) 2015-03-06 2023-01-17 Atea Pharmaceuticals, Inc. .beta.-d-2'-deoxy-2'-.alpha.-fluoro-2'-.beta.-c-substituted-2-modified-n6-substituted purine nucleotides for hcv treatment
US10711029B2 (en) 2016-07-14 2020-07-14 Atea Pharmaceuticals, Inc. Beta-d-2′-deoxy-2′-alpha-fluoro-2′-beta-c-substituted-4′fluoro-n6-substituted-6-amino-2-substituted purine nucleotides for the treatment of hepatitis c virus infection
PT3512863T (pt) 2016-09-07 2022-03-09 Atea Pharmaceuticals Inc Nucleótidos de purina 2'-substituídos-n6-substituídos para tratamento de vírus de rna
GEP20237457B (en) 2017-02-01 2023-01-10 Atea Pharmaceuticals Inc Nucleotide hemi-sulfate salt for treatment of hepatitis c virus
KR20200140865A (ko) 2018-04-10 2020-12-16 아테아 파마슈티컬즈, 인크. 간경변증을 갖는 hcv 감염 환자의 치료
US10874687B1 (en) 2020-02-27 2020-12-29 Atea Pharmaceuticals, Inc. Highly active compounds against COVID-19
WO2021209427A1 (en) * 2020-04-14 2021-10-21 Janssen Sciences Ireland Unlimited Company Spirocyclic nucleoside analogues for the treatment of hepatitis e

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EP2399588B1 (en) * 2001-01-22 2020-04-29 Merck Sharp & Dohme Corp. Nucleoside derivatives as inhibitors of rna-dependent rna viral polymerase
CA2571079A1 (en) * 2004-06-24 2006-02-02 Merck & Co., Inc. Nucleoside aryl phosphoramidates for the treatment of rna-dependent rna viral infection
CA2618335C (en) * 2005-08-15 2015-03-31 F.Hoffmann-La Roche Ag Antiviral phosphoramidates of 4'-substituted pronucleotides
JP2009526850A (ja) * 2006-02-14 2009-07-23 メルク エンド カムパニー インコーポレーテッド Ｒｎａ依存性ｒｎａウイルス感染を治療するためのヌクレオシドアリールホスホルアミデート
PA8852101A1 (es) * 2008-12-08 2010-07-27 Medivir Ab Nucleótidos uracil ciclopropílicos
JO3027B1 (ar) 2009-05-14 2016-09-05 Janssen Products Lp نيوكليوسيدات يوراسيل سبيرواوكسيتان

Also Published As

Publication number Publication date
ME01478B (me) 2014-04-20
AP2011005958A0 (en) 2011-10-31
NI201100197A (es) 2012-05-28
HK1166326A1 (en) 2012-10-26
PT2430035E (pt) 2013-05-22
SMT201400085B (it) 2014-09-08
EP2511282A1 (en) 2012-10-17
US20120065156A1 (en) 2012-03-15
NZ596073A (en) 2013-02-22
CL2011002859A1 (es) 2012-07-20
PT2511282E (pt) 2014-07-11
CA2760329C (en) 2017-10-31
JP2015180692A (ja) 2015-10-15
IL215955A0 (en) 2012-01-31
EP2511282B1 (en) 2014-04-02
SI2511282T1 (sl) 2014-09-30
MY157018A (en) 2016-04-15
DK2430035T3 (da) 2013-05-27
AU2010247439B2 (en) 2014-09-25
ES2477598T3 (es) 2014-07-17
AR076579A1 (es) 2011-06-22
KR20120018355A (ko) 2012-03-02
TWI461432B (zh) 2014-11-21
CY1115383T1 (el) 2017-01-04
WO2010130726A1 (en) 2010-11-18
TW201100442A (en) 2011-01-01
DK2511282T3 (da) 2014-07-07
JP2012526764A (ja) 2012-11-01
SG175981A1 (en) 2011-12-29
CA2760329A1 (en) 2010-11-18
IL215955A (en) 2015-03-31
PL2430035T3 (pl) 2013-08-30
US8933052B2 (en) 2015-01-13
UA105790C2 (ru) 2014-06-25
BRPI1010579A2 (pt) 2016-03-15
US20130217648A1 (en) 2013-08-22
PL2511282T3 (pl) 2014-09-30
EA022084B1 (ru) 2015-10-30
JP5778135B2 (ja) 2015-09-16
HRP20140605T1 (hr) 2014-09-26
AP2783A (en) 2013-10-31
HRP20130554T1 (en) 2013-07-31
ECSP11011461A (es) 2012-02-29
ES2411086T3 (es) 2013-07-04
EP2430035B1 (en) 2013-04-03
SI2430035T1 (sl) 2013-08-30
UY32642A (es) 2010-11-30
HN2011003014A (es) 2014-06-30
CY1114081T1 (el) 2016-07-27
KR101806837B1 (ko) 2017-12-08
JO3027B1 (ar) 2016-09-05
SMT201300078B (it) 2013-09-06
CN102439024B (zh) 2014-09-17
EP2430035A1 (en) 2012-03-21
RS52822B (en) 2013-10-31
MX2011012027A (es) 2012-02-28
CN102439024A (zh) 2012-05-02
CO6440533A2 (es) 2012-05-15
ZA201108309B (en) 2013-04-24
US8481510B2 (en) 2013-07-09
CR20120297A (es) 2012-10-25
AU2010247439A1 (en) 2011-12-01

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