CA2243826A1 - Synthesis of acyclic nucleosides - Google Patents

Synthesis of acyclic nucleosides

Info

Publication number
CA2243826A1
CA2243826A1 CA002243826A CA2243826A CA2243826A1 CA 2243826 A1 CA2243826 A1 CA 2243826A1 CA 002243826 A CA002243826 A CA 002243826A CA 2243826 A CA2243826 A CA 2243826A CA 2243826 A1 CA2243826 A1 CA 2243826A1
Authority
CA
Canada
Prior art keywords
ch2ch3
monounsaturated
saturated
formula
substituted alkyl
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.)
Granted
Application number
CA002243826A
Other languages
French (fr)
Other versions
CA2243826C (en
Inventor
Per Engelhardt
Marita Hogberg
Xiao-Xiong Zhou
Bjorn Lindborg
Nils Gunnar Johansson
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.)
Medivir AB
Original Assignee
Medivir Ab
Per Engelhardt
Marita Hogberg
Xiao-Xiong Zhou
Bjorn Lindborg
Nils Gunnar Johansson
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 SE9600614A external-priority patent/SE9600614D0/en
Priority claimed from SE9600613A external-priority patent/SE9600613D0/en
Application filed by Medivir Ab, Per Engelhardt, Marita Hogberg, Xiao-Xiong Zhou, Bjorn Lindborg, Nils Gunnar Johansson filed Critical Medivir Ab
Publication of CA2243826A1 publication Critical patent/CA2243826A1/en
Application granted granted Critical
Publication of CA2243826C publication Critical patent/CA2243826C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • 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
    • A61P31/18—Antivirals for RNA viruses for HIV
    • 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
    • A61P31/22—Antivirals for DNA viruses for herpes viruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
    • C07D473/18—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 one oxygen and one nitrogen atom, e.g. guanine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
    • C07D473/32—Nitrogen atom
    • 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

Abstract

A method for preparing enhanced bioavailability antiviral compounds of formula (I) where one of R1 and R2 is -C(O)CH(CH(CH3)2)NH2 or -C(O)CH(CH(CH3)CH2CH3)NH2 and the other of R1 and R2 is -C(O)C3-C21 saturated or monounsaturated, optionally substituted alkyl; and R3 is OH or H, the method comprising: A) the monodeacylation of a diacylated compound corresponding to formula (I) wherein R1 and R2 are both -C(O)CH(CH(CH3)2)NH2 or -C(O)CH(CH(CH3)CH2CH3)NH2 (which are optionally N-protected) or R1 and R2 are both -C(=O)C3-C21, saturated or monounsaturated, optionally substituted alkyl; B) acylating the thus liberated side chain 4-hydroxy or side chain 2-hydroxymethyl group with the corresponding -C(O)CH(CH(CH3)2)NH2 or -C(O)CH(CH(CH3)CH2CH3)NH2 or -C(=O)C3-C21, saturated or monounsaturated, optionally substituted alkyl to thereby produce a compound of formula (I); and C) deprotecting as necessary.
CA002243826A 1996-02-16 1997-02-14 Synthesis of acyclic nucleosides Expired - Fee Related CA2243826C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
SE9600614A SE9600614D0 (en) 1996-02-16 1996-02-16 Antiviral compounds
SE9600613-5 1996-02-16
SE9600614-3 1996-02-16
SE9600613A SE9600613D0 (en) 1996-02-16 1996-02-16 Acyclic nucleoside derivatives
PCT/SE1997/000242 WO1997030052A1 (en) 1996-02-16 1997-02-14 Synthesis of acyclic nucleosides

Publications (2)

Publication Number Publication Date
CA2243826A1 true CA2243826A1 (en) 1997-08-21
CA2243826C CA2243826C (en) 2005-12-27

Family

ID=26662518

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002243826A Expired - Fee Related CA2243826C (en) 1996-02-16 1997-02-14 Synthesis of acyclic nucleosides

Country Status (26)

Country Link
US (5) US5869493A (en)
EP (2) EP0880521B1 (en)
JP (2) JP2000504721A (en)
KR (1) KR100464692B1 (en)
CN (1) CN1067073C (en)
AR (1) AR005827A1 (en)
AT (2) ATE231507T1 (en)
AU (1) AU715062B2 (en)
BG (1) BG64179B1 (en)
CA (1) CA2243826C (en)
CZ (1) CZ292169B6 (en)
DE (2) DE69718626T2 (en)
DK (1) DK0888348T3 (en)
EA (2) EA001404B1 (en)
ES (2) ES2189942T3 (en)
HK (1) HK1015773A1 (en)
HU (1) HU229865B1 (en)
IL (1) IL124760A (en)
MY (1) MY123083A (en)
NO (1) NO322930B1 (en)
NZ (1) NZ330472A (en)
PL (1) PL184892B1 (en)
SK (1) SK284613B6 (en)
TR (1) TR199801318T2 (en)
TW (1) TW533213B (en)
WO (2) WO1997030052A1 (en)

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US5869493A (en) 1996-02-16 1999-02-09 Medivir Ab Acyclic nucleoside derivatives
US6703394B2 (en) 1996-02-16 2004-03-09 Medivir Ab Acyclic nucleoside derivatives
JP2001503767A (en) * 1996-11-12 2001-03-21 メディヴィル・アクチボラグ Nucleoside
ES2186127T3 (en) * 1997-02-10 2003-05-01 Medivir Ab SYNTHESIS OF ACICLIC NUCLEOSID DERIVATIVES.
US6184376B1 (en) * 1997-02-10 2001-02-06 Mediver Ab Synthesis of acyclic nucleoside derivatives
PL338643A1 (en) * 1997-08-15 2000-11-06 Medivir Ab Nucleosidic analoques such as antiviral ones comprising inhibitors of retrovirus revertase and dna polymerase of b type viral hepatic (hbv)
AU1711599A (en) * 1997-12-19 1999-07-12 Bristol-Myers Squibb Company Prodrugs of lobucavir and methods of use
US20040266795A1 (en) * 2003-04-30 2004-12-30 Genny Shamai Process for the preparation of famciclovir
AU2005321239B2 (en) 2004-12-30 2009-02-12 Medivir Ab Compounds useful in the treatment of HIV
US20080233053A1 (en) * 2005-02-07 2008-09-25 Pharmalight Inc. Method and Device for Ophthalmic Administration of Active Pharmaceutical Ingredients
CN101033238B (en) * 2006-03-06 2011-02-16 中国科学院上海药物研究所 Preparation method and use for purine compounds double amino acid ester
ZA200702234B (en) * 2006-03-21 2008-07-30 Cipla Ltd Preparation of ester of purine derivatives
MX2010000424A (en) 2007-07-09 2010-08-10 Easter Virginia Medical School Substituted nucleoside derivatives with antiviral and antimicrobial properties.
US20100240681A1 (en) 2007-09-21 2010-09-23 Epiphany Biosciences, Inc. Valomaciclovir polymorphs
WO2011022712A1 (en) * 2009-08-21 2011-02-24 Epiphany Biosciences, Inc. Method of treating infectious mononucleosis with acylic nucleoside derivatives
AU2012267786B2 (en) 2011-06-10 2017-08-03 Oregon Health & Science University CMV glycoproteins and recombinant vectors
KR101763127B1 (en) 2015-06-23 2017-08-01 (주)농협아그로 Sticky and embossed trap tape

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Also Published As

Publication number Publication date
AU715062B2 (en) 2000-01-13
HK1015773A1 (en) 1999-10-22
US6576763B1 (en) 2003-06-10
US20090076041A1 (en) 2009-03-19
TR199801318T2 (en) 1998-10-21
ES2189941T3 (en) 2003-07-16
BG102647A (en) 1999-04-30
JP2000504720A (en) 2000-04-18
AR005827A1 (en) 1999-07-14
NO983216L (en) 1998-10-13
NO983216D0 (en) 1998-07-13
ATE231508T1 (en) 2003-02-15
JP4171069B2 (en) 2008-10-22
EA199800729A1 (en) 1999-02-25
US5869493A (en) 1999-02-09
AU1818397A (en) 1997-09-02
IL124760A (en) 2003-09-17
US8124609B2 (en) 2012-02-28
JP2000504721A (en) 2000-04-18
BG64179B1 (en) 2004-03-31
DE69718626T2 (en) 2003-09-11
NO322930B1 (en) 2006-12-18
EA001404B1 (en) 2001-02-26
DK0888348T3 (en) 2003-04-14
MY123083A (en) 2006-05-31
HU229865B1 (en) 2014-10-28
CZ232298A3 (en) 1998-10-14
EP0880521A1 (en) 1998-12-02
CN1210537A (en) 1999-03-10
WO1997030051A1 (en) 1997-08-21
KR19990082571A (en) 1999-11-25
PL184892B1 (en) 2003-01-31
CA2243826C (en) 2005-12-27
KR100464692B1 (en) 2005-06-21
AU713916B2 (en) 1999-12-16
WO1997030052A1 (en) 1997-08-21
DE69718626D1 (en) 2003-02-27
TW533213B (en) 2003-05-21
SK98598A3 (en) 1998-12-02
EP0888348A1 (en) 1999-01-07
DE69718619D1 (en) 2003-02-27
EP0880521B1 (en) 2003-01-22
US6255312B1 (en) 2001-07-03
EA002809B1 (en) 2002-10-31
ES2189942T3 (en) 2003-07-16
CN1067073C (en) 2001-06-13
IL124760A0 (en) 1999-01-26
ATE231507T1 (en) 2003-02-15
EA200000787A1 (en) 2001-04-23
AU1818297A (en) 1997-09-02
HUP9900680A2 (en) 1999-06-28
SK284613B6 (en) 2005-07-01
EP0888348B1 (en) 2003-01-22
PL328335A1 (en) 1999-01-18
HUP9900680A3 (en) 2001-02-28
CZ292169B6 (en) 2003-08-13
DE69718619T2 (en) 2003-08-21
NZ330472A (en) 2000-02-28
US20120123119A1 (en) 2012-05-17

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Effective date: 20140214