GB1163103A - Ribofuranosyl Purine Derivatives - Google Patents
Ribofuranosyl Purine DerivativesInfo
- Publication number
- GB1163103A GB1163103A GB4992466A GB4992466A GB1163103A GB 1163103 A GB1163103 A GB 1163103A GB 4992466 A GB4992466 A GB 4992466A GB 4992466 A GB4992466 A GB 4992466A GB 1163103 A GB1163103 A GB 1163103A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkyl
- acyl
- formula
- halogen
- radical
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Abstract
1,163,103. Ribofuranosyl purine derivatives. MERCK & CO. Inc. 8 Nov., 1966 [15 Nov., 1965], No. 49924/66. Heading C2C. Novel nucleosides of the formula where R is a C 1-5 alkyl radical and each of Ra and Rb is a hydrogen or halogen atom or a hydroxy, C 1-5 alkyl, amino, C 1-5 alkylamino, di- (C 1-5 alkyl) amino, mercapto or C 1-5 alkyl mercapto radical, are prepared by treating 2,3,5 - tri - O - acyl - 3 - C 1-5 - alkyl - D - ribofuranosyl halides II with a chloromercuri-2,6- substituted purines of the formula where each of Rc and Rd is a halogen or hydrogen atom or a hydroxy, C 1-5 alkyl, acylamino or acyl C 1-5 alkylamino to produce the corresponding 9 - (2,3,5 - tri - 0 - acyl - 3 - C 1-5 - alkyl- D - ribofuranosyl) - 2,6 - substituted purine derivatives IV and either (a) hydrolysing these by a basic solvolysis reaction to give a compound of Formula I in which each of Ra and/or Rb is a hydrogen or halogen atom or a hydroxy, C 1-5 alkyl, amino or C 1-5 alkylamino radical or (b) when Rc and/or Rd is halogen, reacting compounds IV with primary or secondary amines to give compounds of Formula I in which Ra and/or Rb is a C 1-5 alkylamino or di-(C 1-5 alkyl) amino radical or (c) when Rc and/or Rd is halogen, subjecting compounds IV to mercaptolysis to give compounds of Formula I in which Ra and/or Rb is a mercapto or C 1-5 alkyl mercapto radical or (d) when Rc and/or Rd is halogen, hydrogenating and solvolysing compounds IV to give compounds of Formula I in which Ra and/or Rb is hydrogen. In the mercaptolysis reaction (c), a (tri-acyl-3-C 1-5 alkyl ribosyl) purine thiol may be formed as an intermediate. The 2,3,5 - tri - 0 - acyl - 3 - C 1-5 alkyl - D- ribofuranosyl halides II may be prepared by reacting a 5-0-acyl-1,2-O-isopropylidene-D- erythro-3-pentulofuranose with a Grignard reagent, thereby forming a 5-0-acyl-1,2-0-isopropylidene - 3 - C 1-5 alkyl - D - ribofuranose, subjecting this to acid alcoholysis to produce an alkyl 5 - O - acyl - 3 - C 1-5 alkyl - D - ribofuranoside, acylating this first to the alkyl 2,5-di-0- acyl- and then to the alkyl 2,3,5-triacyl-3-C 1-5 alkyl-D-ribofuranoside which is then subjected to a halogen replacement reaction. The above nucleosides are biologically active and are useful as antimetabolites and cellgrowth inhibitors.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US50771865A | 1965-11-15 | 1965-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1163103A true GB1163103A (en) | 1969-09-04 |
Family
ID=24019834
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4992466A Expired GB1163103A (en) | 1965-11-15 | 1966-11-08 | Ribofuranosyl Purine Derivatives |
Country Status (5)
| Country | Link |
|---|---|
| CH (1) | CH490395A (en) |
| DE (1) | DE1620053A1 (en) |
| FR (1) | FR1504091A (en) |
| GB (1) | GB1163103A (en) |
| NL (1) | NL6615905A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2001090121A3 (en) * | 2000-05-23 | 2002-05-02 | Novirio Pharmaceuticals Ltd | Methods and compositions for treating hepatitis c virus |
| WO2001092282A3 (en) * | 2000-05-26 | 2002-05-02 | Novirio Pharmaceuticals Ltd | Methods and compositions for treating flaviviruses and pestiviruses |
| WO2004003000A3 (en) * | 2002-06-28 | 2004-11-04 | Idenix Cayman Ltd | 1’-, 2'- and 3'- modified nucleoside derivatives for treating flaviviridae infections |
| US7094770B2 (en) | 2000-04-13 | 2006-08-22 | Pharmasset, Ltd. | 3′-or 2′-hydroxymethyl substituted nucleoside derivatives for treatment of hepatitis virus infections |
| US7138376B2 (en) | 2001-09-28 | 2006-11-21 | Idenix Pharmaceuticals, Inc. | Methods and compositions for treating hepatitis C virus using 4'-modified nucleosides |
| US7192936B2 (en) | 2002-06-28 | 2007-03-20 | Idenix Pharmaceuticals, Inc. | Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
| US7625875B2 (en) | 2002-06-28 | 2009-12-01 | Idenix Pharmaceuticals, Inc. | 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
| US7781576B2 (en) | 2005-12-23 | 2010-08-24 | Idenix Pharmaceuticals, Inc. | Process for preparing a synthetic intermediate for preparation of branched nucleosides |
| US7824851B2 (en) | 2002-11-15 | 2010-11-02 | Idenix Pharmaceuticals, Inc. | 2′-branched nucleosides and Flaviviridae mutation |
-
1966
- 1966-11-08 CH CH1606766A patent/CH490395A/en not_active IP Right Cessation
- 1966-11-08 GB GB4992466A patent/GB1163103A/en not_active Expired
- 1966-11-10 NL NL6615905A patent/NL6615905A/xx unknown
- 1966-11-14 DE DE19661620053 patent/DE1620053A1/en active Pending
- 1966-11-14 FR FR83545A patent/FR1504091A/en not_active Expired
Cited By (35)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7094770B2 (en) | 2000-04-13 | 2006-08-22 | Pharmasset, Ltd. | 3′-or 2′-hydroxymethyl substituted nucleoside derivatives for treatment of hepatitis virus infections |
| US7157441B2 (en) | 2000-05-23 | 2007-01-02 | Idenix Pharmaceuticals, Inc. | Methods and compositions for treating hepatitis C virus |
| US8299038B2 (en) | 2000-05-23 | 2012-10-30 | Idenix Pharmaceuticals, Inc. | Methods and compositions for treating hepatitis C virus |
| EA011720B1 (en) * | 2000-05-23 | 2009-04-28 | Айденикс (Кайман) Лимитед | β-D NUCLEOSIDE DERIVATIVES |
| US10758557B2 (en) | 2000-05-23 | 2020-09-01 | Idenix Pharmaceuticals Llc | Methods and compositions for treating hepatitis C virus |
| US6914054B2 (en) | 2000-05-23 | 2005-07-05 | Idenix Pharmaceuticals, Inc. | Methods and compositions for treating hepatitis C virus |
| EA007178B1 (en) * | 2000-05-23 | 2006-08-25 | Айденикс (Кайман) Лимитед | Methods and compositions for treating hepatitis c virus |
| US10363265B2 (en) | 2000-05-23 | 2019-07-30 | Idenix Pharmaceuticals Llc | Methods and compositions for treating hepatitis C virus |
| WO2001090121A3 (en) * | 2000-05-23 | 2002-05-02 | Novirio Pharmaceuticals Ltd | Methods and compositions for treating hepatitis c virus |
| US7169766B2 (en) | 2000-05-23 | 2007-01-30 | Idenix Pharmaceuticals, Inc. | Methods and compositions for treating hepatitis C virus |
| SG156517A1 (en) * | 2000-05-23 | 2009-11-26 | Idenix Cayman Ltd | Methods and compositions for treating hepatitis c virus |
| US7148206B2 (en) | 2000-05-26 | 2006-12-12 | Idenix Pharmaceuticals, Inc. | Methods and compositions for treating flaviviruses and pestiviruses |
| US7163929B2 (en) | 2000-05-26 | 2007-01-16 | Idenix Pharmaceuticals, Inc. | Methods and compositions for treating flaviviruses and pestiviruses |
| EA007867B1 (en) * | 2000-05-26 | 2007-02-27 | Айденикс (Кайман) Лимитед | Methods and compositions for treating flaviviruses and pestiviruses |
| AP1727A (en) * | 2000-05-26 | 2007-03-06 | Idenix Cayman Ltd | Methods and compositions for treating flaviviruses and pestiviruses. |
| US7105493B2 (en) | 2000-05-26 | 2006-09-12 | Idenix Pharmaceuticals, Inc. | Methods and compositions for treating flaviviruses and pestiviruses |
| US7101861B2 (en) | 2000-05-26 | 2006-09-05 | Indenix Pharmaceuticals, Inc. | Methods and compositions for treating flaviviruses and pestiviruses |
| US9968628B2 (en) | 2000-05-26 | 2018-05-15 | Idenix Pharmaceuticals Llc | Methods and compositions for treating flaviviruses and pestiviruses |
| US6812219B2 (en) | 2000-05-26 | 2004-11-02 | Idenix Pharmaceuticals, Inc. | Methods and compositions for treating flaviviruses and pestiviruses |
| US8343937B2 (en) | 2000-05-26 | 2013-01-01 | Idenix Pharmaceuticals, Inc. | Methods and compositions for treating flaviviruses and pestiviruses |
| WO2001092282A3 (en) * | 2000-05-26 | 2002-05-02 | Novirio Pharmaceuticals Ltd | Methods and compositions for treating flaviviruses and pestiviruses |
| US7138376B2 (en) | 2001-09-28 | 2006-11-21 | Idenix Pharmaceuticals, Inc. | Methods and compositions for treating hepatitis C virus using 4'-modified nucleosides |
| US7192936B2 (en) | 2002-06-28 | 2007-03-20 | Idenix Pharmaceuticals, Inc. | Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
| US7625875B2 (en) | 2002-06-28 | 2009-12-01 | Idenix Pharmaceuticals, Inc. | 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
| US7635689B2 (en) | 2002-06-28 | 2009-12-22 | Idenix Pharmaceuticals, Inc. | Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
| US7662798B2 (en) | 2002-06-28 | 2010-02-16 | Idenix Pharmaceuticals, Inc. | 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
| US7608600B2 (en) | 2002-06-28 | 2009-10-27 | Idenix Pharmaceuticals, Inc. | Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
| US7547704B2 (en) | 2002-06-28 | 2009-06-16 | Idenix Pharmaceuticals, Inc. | Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
| US7384924B2 (en) | 2002-06-28 | 2008-06-10 | Idenix Pharmaceuticals, Inc. | Modified 2′ and 3′-nucleoside prodrugs for treating Flaviviridae infections |
| US7365057B2 (en) | 2002-06-28 | 2008-04-29 | Idenix Pharmaceuticals, Inc. | Modified 2′ and 3′-nucleoside prodrugs for treating Flavivridae infections |
| WO2004003000A3 (en) * | 2002-06-28 | 2004-11-04 | Idenix Cayman Ltd | 1’-, 2'- and 3'- modified nucleoside derivatives for treating flaviviridae infections |
| US7824851B2 (en) | 2002-11-15 | 2010-11-02 | Idenix Pharmaceuticals, Inc. | 2′-branched nucleosides and Flaviviridae mutation |
| US8674085B2 (en) | 2002-11-15 | 2014-03-18 | Idenix Pharmaceuticals, Inc. | 2′-branched nucleosides and Flaviviridae mutation |
| US10525072B2 (en) | 2002-11-15 | 2020-01-07 | Idenix Pharmaceuticals Llc | 2′-branched nucleosides and flaviviridae mutation |
| US7781576B2 (en) | 2005-12-23 | 2010-08-24 | Idenix Pharmaceuticals, Inc. | Process for preparing a synthetic intermediate for preparation of branched nucleosides |
Also Published As
| Publication number | Publication date |
|---|---|
| CH490395A (en) | 1970-05-15 |
| NL6615905A (en) | 1967-05-16 |
| FR1504091A (en) | 1967-12-01 |
| DE1620053A1 (en) | 1970-03-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |