AR074977A1 - Sintesis de nucleosidos de purina - Google Patents

Sintesis de nucleosidos de purina

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Publication number
AR074977A1
AR074977A1 ARP090105094A ARP090105094A AR074977A1 AR 074977 A1 AR074977 A1 AR 074977A1 AR P090105094 A ARP090105094 A AR P090105094A AR P090105094 A ARP090105094 A AR P090105094A AR 074977 A1 AR074977 A1 AR 074977A1
Authority
AR
Argentina
Prior art keywords
alkyl
optionally substituted
cycloalkyl
halogenated
alkynyl
Prior art date
Application number
ARP090105094A
Other languages
English (en)
Inventor
Byoung-Kwon Chun
Jinfa Du
Dhanapalan Nagarathnam
Ganapati Reddy Pamulapati
Suguna Rachakonda
Bruce Ross
Michael Sofia
Wonsuk Chang
Hai-Ren Zhang
Original Assignee
Pharmasset Inc
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Publication date
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=41683220&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=AR074977(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Pharmasset Inc filed Critical Pharmasset Inc
Publication of AR074977A1 publication Critical patent/AR074977A1/es

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Classifications

    • 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
    • C07H19/16—Purine radicals
    • C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • 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
    • A61K31/7076—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 containing purines, e.g. adenosine, adenylic acid
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • 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
    • 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
    • C07H19/16—Purine radicals
    • C07H19/167—Purine radicals with ribosyl as the saccharide radical
    • 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
    • C07H19/16—Purine radicals
    • C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C07H19/213—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids containing cyclic phosphate
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/02—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to halogen
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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

Abstract

Un proceso para preparar profármacos de fosforamidato o profármacos de fosfato cíclicos de derivados de nucleosido, que es un compuesto, sus estereoisomeros, sales (sales de adicion ácida o básica), hidratos, solvatos, o formas cristalinas de los mismos, y agente antiviral. Composicion farmacéutica. Reivindicacion 1: Un compuesto (1) o una sal del mismo o el compuesto (2) o una sal del mismo: caracterizado porque (a) R1 es hidrogeno, n-alquilo; alquilo ramificado; cicloalquilo; o arilo, que incluye, pero no se limita a, fenilo o naftilo, donde fenilo o naftilo están opcionalmente sustituidos con al menos uno de alquilo C1-6, alquenilo C2-6, alquinilo C2-6, alcoxi C1-6, F, Cl, Br, I, nitro, ciano, haloalquilo C1-6, -N(R1')2, acilamino C1-6, -NHSO2 alquilo C1-6, -SO2N(R1')2, COR1'', y -SO2 alquilo C1-6; (R1' es independientemente hidrogeno o alquilo, que incluye, pero no se limita a, alquilo C1-20, alquilo C1-10, o alquilo C1-6, R1'' es -OR' o -N(R1')2); (b) R2 es hidrogeno, alquilo C1-10, o R3a o R3b y R2 juntos son (CH2)n de manera que forman el anillo cíclico que incluye los átomos N y C contiguos, donde n es 2 hasta 4; (c) R3a y R3b son (i) independientemente seleccionado de hidrogeno, alquilo C1-10, cicloalquilo, -(CH2)c(NR3')2, hidroxialquilo C1-6, -CH2SH, -(CH2)2S(O)dMe, -(CH2)3NHC(=NH)NH2, (1H-indol-3-il)metilo, (1H-imidazol-4-il)metilo, -(CH2)eCOR3'', arilo y aril alquilo C1-3, los grupos arilo opcionalmente sustituidos con un grupo seleccionado de hidroxil, alquilo C1-10, alcoxi C1-6, halogeno, nitro y ciano; (ii) R3a y R3b ambos son alquilo C1-6; (iii) R3a y R3b juntos son (CH2)f de manera que forman un anillo espiro; (iv) R3a es hidrogeno y R3b y R2 juntos con (CH2)n de manera que forman el anillo cíclico que incluye los átomos N y C contiguos (v) R3b es hidrogeno y R3a y R2 juntos son (CH2)n de manera que forman el anillo cíclico que incluye los átomos N y C contiguos, donde c es 1 hasta 6, d es 0 hasta 2, e es 0 hasta 3, f es 2 hasta 5, n es 2 hasta 4, y donde R3' es independientemente hidrogeno o alquilo C1-6 y R3'' es -OR' o -N(R3')2); (vi) R3a es H y R3b es H, CH3, CH2CH3, CH(CH3)2, CH2CH(CH3)2, CH(CH3)CH2CH3, CH2Ph, CH2-indol-3-ilo, CH2CH2SCH3, CH2CO2H, CH2C(O)NH2, CH2CH2COOH, CH2CH2C(O)NH2, CH2CH2CH2CH2NH2, -CH2CH2CH2NHC(NH)NH2, CH2-imidazol-4-ilo, CH2OH, CH(OH)CH3, CH2((4'-OH)-Ph), CH2SH, o cicloalquilo inferior; o (vii) R3a es CH3, -CH2CH3, CH(CH3)2, CH2CH(CH3)2, CH(CH3)CH2CH3, CH2Ph, CH2-indol-3-ilo, -CH2CH2SCH3, CH2CO2H, CH2C(O)NH2, CH2CH2COOH, CH2CH2C(O)NH2, CH2CH2CH2CH2NH2, -CH2CH2CH2NHC(NH)NH2, CH2-imidazol-4-ilo, CH2OH, CH(O)CH3, CH2((4'-OH)-Ph), CH2SH, o cicloalquilo inferior y R3b es H, donde R3' es independientemente hidrogeno o alquilo, que incluye, pero no se limita a, alquilo C1-20, alquilo C1-10, o alquilo C1-6, R3'' es -OR' o -N(R3')2); (d) R4 es hidrogeno, alquilo C1-10, alquilo C1-10 opcionalmente sustituido con un alquilo inferior, alcoxi, di(alquilo inferior)-amino, o halogeno, haloalquilo C1-10, cicloalquilo C3-10, cicloalquil alquilo, cicloheteroalquilo, aminoacilo, arilo, tal como fenilo, heteroarilo, tal como, piridinilo, arilo sustituido, o heteroarilo sustituido; (e) R5 es H, un alquilo inferior, CN, vinilo, O-(alquilo inferior), hidroxi alquilo inferior, es decir, (CH2)pOH, donde p es 1-6, incluyendo hidroxil metil (CH2OH), CH2F, N3, CH2CN, CH2NH2, CH2NHCH3, CH2N(CH3)2, alquino (opcionalmente sustituido), o halogeno, incluyendo F, Cl, Br, o I; (f) R6 es H, CH3, CH2F, CHF2, CF3, F, CN, vinilo, o etinilo; (g) R7 es hidrogeno, n-alquilo, alquilo ramificado, cicloalquilo, alcarilo, o arilo, que incluye, pero no se limita a, fenilo o naftilo, donde fenilo o naftilo están opcionalmente sustituidos con al menos uno de H, F, Cl, Br, I, OH, OR7', SH, SR7', NH2, NHR7', NR7'2, alquilo inferior de C1-6, alquilo inferior halogenado (F, Cl, Br, I) de C1-6, alquenilo inferior halogenado (F, Cl, Br, I) de C2-6, alquinilo inferior de C2-6, tal como C:::CH, alquinilo inferior halogenado (F, Cl, Br, I) de C2-6), alcoxi inferior de C1-6, alcoxi inferior halogenado (F, Cl, Br, I) de C1-6, CO2H, CO2R7', CONH2, CONHR7', CONR7'2, CH=CHCO2H, o CH=CHCO2R7' en donde R7' es un alquilo opcionalmente sustituido, cicloalquilo, alquenilo, alquinilo, o alcoxialquilo, que incluye, pero no se limita a, alquilo C1-10, cicloalquilo C3-7, alquenilo C2-10, alquinilo C2-10, y alcoxialquilo C1-10, (h) X es H, OH, OMe, halogeno, CN, NH2, o N3; (i) Y es OH; (j) Z es N o CR10; (k) R8 y R9 son independientemente H, F, Cl, Br, I, OH, OR', SH, SR', NH2, NHr', NR'2, nitrogeno heterociclo, alquilo inferior de C1-6, alquilo inferior halogenado (F, Cl, Br, I) de C1-6, alquenilo inferior de C2-6, alquenilo inferior halogenado (F, Cl, Br, I) de C2-6, alquinilo inferior de C2-6 tal como C:::CH, alquinilo inferior halogenado (F, Cl, Br, I) de C2-6), alcoxi inferior de C1-6, alcoxi inferiorhalogenado (F, Cl, Br, I) de C1-6, CO2H, CO2R', CONH2, CONHR', CONR'2, CH=CHCO2H, o CH=CHCO2R', y (1) R10 es H, halogeno, (incluyendo F, Cl, Br, I), OH, OR', SH, SR', NH2, NHR', NR'2, NO2 alquilo inferior de C1-6, halogenado (F, Cl, Br, I) alquilo inferior de C1-6, alquenilo inferior de C2-6, alquenilo inferior halogenado (F, Cl, Br, I) de C2-6, alquinilo inferior de C2-6, alquinilo inferior halogenado (F, Cl, Br, I) de C2-6, alcoxi inferior de C1-6, alcoxi inferior halogenado (F, Cl, Br, I) de C1-6, CO2H, CO2R', CONH2, CONHR', CONR'2, CH=CHCO2H, O CH=CHCO2R'; en donde R' es un alquilo opcionalmente sustituido, que incluye, pero no se limita a, un alquilo C1-20 opcionalmente sustituido, un alquilo C1-10 opcionalmente sustituido, un alquilo inferior opcionalmente sustituido; un cicloalquilo opcionalmente sustituido; un alcarilo; un alquinilo de C2-6 opcionalmente sustituido, un alquenilo inferior de C2-6 opcionalmente sustituido, o acilo opcionalmente sustituido, que incluye pero no se limita a C(O) alquilo, C(O)(alquilo C1-20), C(O)(alquilo C1-10), o un C(O)(alquilo inferior).
ARP090105094A 2008-12-23 2009-12-23 Sintesis de nucleosidos de purina AR074977A1 (es)

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Country Status (19)

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US (2) US8716263B2 (es)
EP (2) EP2376515A1 (es)
JP (4) JP5793084B2 (es)
KR (1) KR20110104074A (es)
CN (1) CN102325783A (es)
AR (1) AR074977A1 (es)
AU (1) AU2009329872B2 (es)
BR (1) BRPI0923815A2 (es)
CA (1) CA2748016A1 (es)
CL (1) CL2009002206A1 (es)
CO (1) CO6400228A2 (es)
EA (1) EA019295B1 (es)
IL (1) IL213701A0 (es)
MX (1) MX2011006892A (es)
NZ (1) NZ593647A (es)
PA (1) PA8855801A1 (es)
SG (2) SG194404A1 (es)
TW (1) TW201031675A (es)
WO (1) WO2010075554A1 (es)

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