ES2138537B1 - PROCEDURE FOR THE PREPARATION OF THE ANTIVIRAL COMPOUNDS PENCICLOVIR AND FAMCICLOVIR. - Google Patents

PROCEDURE FOR THE PREPARATION OF THE ANTIVIRAL COMPOUNDS PENCICLOVIR AND FAMCICLOVIR.

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Publication number
ES2138537B1
ES2138537B1 ES9701615A ES9701615A ES2138537B1 ES 2138537 B1 ES2138537 B1 ES 2138537B1 ES 9701615 A ES9701615 A ES 9701615A ES 9701615 A ES9701615 A ES 9701615A ES 2138537 B1 ES2138537 B1 ES 2138537B1
Authority
ES
Spain
Prior art keywords
sub
carboxy
hydrogen
penciclovir
famciclovir
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
ES9701615A
Other languages
Spanish (es)
Other versions
ES2138537A1 (en
Inventor
Victor Witold Jacewicz
David Alan Jones
Norman John Lewis
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.)
SmithKline Beecham Ltd
Original Assignee
SmithKline Beecham Ltd
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
Application filed by SmithKline Beecham Ltd filed Critical SmithKline Beecham Ltd
Publication of ES2138537A1 publication Critical patent/ES2138537A1/en
Application granted granted Critical
Publication of ES2138537B1 publication Critical patent/ES2138537B1/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

Procedimiento para la preparación de los compuestos antivirales penciclovir y famciclovir. Un procedimiento para la preparación de: penciclovir o famciclovir, que comprende una o más de las siguiente etapas: a) formar una purina mediante el cierre del anillo de imidazol o pirimidina; b) hacer reaccionar una purina con un intermedio precursor de cadena lateral en posición 9 adecuado; c) convertir la cadena lateral en posición 9 en: 4-hidroxi-3-hidroximetilbut-l-ilo o 4-acetoxi-3-acetoximetilbut-l-ilo d) convertir una purina en guanina o 2-aminopurina, caracterizado porque la purina tiene la fórmula (I): en la que uno de X{sub,1 , y X{sub,2 , es ciano o carboxi o un derivado de carboxi; y el otro se selecciona entre: X{sub,1 , es ciano o carboxi o un derivado de carboxi, o hidrógeno, o hidroxi, o un radical que pueda convertirse en hidrógeno o hidroxi; X{sub,2 es ciano o carboxi o un derivado de carboxi, o hidrógeno, o un radical que pueda convertirse en hidrógeno; R{sub,1 , es amino o un grupo que pueda convertirse en el mismo; y R{sub,2 , es hidrógeno o una cadena lateral en posición 9; que se convierte e famciclovir o penciclovir: cuando X{sub,1 , y/o X{sub,2 , es ciano o un derivado de carboxi, se convierte e carboxi; y cuando X{sub,1 , y/o X{sub,2 es carboxi, se convierte en X{sub,1 y/o X {sub,2 hidrógeno por descarboxilación; y/o cuando X{sub,1 es carboxi se convierte en X{sub,1 , hidroxi por hidrólisis.Procedure for the preparation of the antiviral compounds penciclovir and famciclovir. A process for the preparation of: penciclovir or famciclovir, comprising one or more of the following steps: a) forming a purine by closing the imidazole or pyrimidine ring; b) reacting a purine with a suitable 9-side chain precursor intermediate; c) converting the side chain in position 9 to: 4-hydroxy-3-hydroxymethylbut-l-yl or 4-acetoxy-3-acetoxymethylbut-l-yl d) converting a purine to guanine or 2-aminopurine, characterized in that the purine has the formula (I): wherein one of X {sub, 1, and X {sub, 2, is cyano or carboxy or a carboxy derivative; and the other is selected from: X {sub, 1, is cyano or carboxy or a derivative of carboxy, or hydrogen, or hydroxy, or a radical that can be converted to hydrogen or hydroxy; X {sub, 2 is cyano or carboxy or a carboxy derivative, or hydrogen, or a radical that can be converted to hydrogen; R {sub, 1, is amino or a group that can become the same; and R {sub, 2, is hydrogen or a side chain at position 9; that e famciclovir or penciclovir is converted: when X {sub, 1, and / or X {sub, 2, is cyano or a carboxy derivative, e carboxy is converted; and when X {sub, 1, and / or X {sub, 2 is carboxy, it becomes X {sub, 1 and / or X {sub, 2 hydrogen by decarboxylation; and / or when X {sub, 1 is carboxy it is converted to X {sub, 1, hydroxy by hydrolysis.

ES9701615A 1996-07-20 1997-07-18 PROCEDURE FOR THE PREPARATION OF THE ANTIVIRAL COMPOUNDS PENCICLOVIR AND FAMCICLOVIR. Expired - Fee Related ES2138537B1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GBGB9615276.4A GB9615276D0 (en) 1996-07-20 1996-07-20 Pharmaceuticals

Publications (2)

Publication Number Publication Date
ES2138537A1 ES2138537A1 (en) 2000-01-01
ES2138537B1 true ES2138537B1 (en) 2000-11-16

Family

ID=10797241

Family Applications (1)

Application Number Title Priority Date Filing Date
ES9701615A Expired - Fee Related ES2138537B1 (en) 1996-07-20 1997-07-18 PROCEDURE FOR THE PREPARATION OF THE ANTIVIRAL COMPOUNDS PENCICLOVIR AND FAMCICLOVIR.

Country Status (5)

Country Link
AT (1) AT412872B (en)
ES (1) ES2138537B1 (en)
GB (1) GB9615276D0 (en)
GR (1) GR1002942B (en)
PT (1) PT102027B (en)

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0141927B1 (en) * 1983-08-18 1991-10-30 Beecham Group Plc Antiviral guanine derivatives
IL73682A (en) * 1983-12-20 1991-08-16 Medivir Ab Antiviral pharmaceutical compositions containing 9-hydroxy aliphatic derivatives of guanine,some new such derivatives and process for their preparation
EP0152316B1 (en) * 1984-01-26 1989-07-26 Merck & Co. Inc. Substituted butyl guanines and their utilization in antiviral compositions
EP0182024B1 (en) * 1984-09-20 1991-04-03 Beecham Group Plc Purine derivatives and their pharmaceutical use
SE8406538D0 (en) * 1984-12-21 1984-12-21 Astra Laekemedel Ab NOVEL DERIVATIVES OF PURINE
DE3671227D1 (en) * 1985-07-27 1990-06-21 Beecham Group Plc 9-SUBSTITUTED GUANINE MONOHYDRATES.
GB8817270D0 (en) * 1988-07-20 1988-08-24 Beecham Group Plc Novel process
GB8817607D0 (en) * 1988-07-23 1988-09-01 Beecham Group Plc Novel process
GB8822236D0 (en) * 1988-09-21 1988-10-26 Beecham Group Plc Chemical process
GB8922076D0 (en) * 1989-09-28 1989-11-15 Beecham Group Plc Novel process
GB9407698D0 (en) * 1994-04-19 1994-06-15 Smithkline Beecham Plc Pharmaceuticals

Also Published As

Publication number Publication date
GR1002942B (en) 1998-07-21
PT102027A (en) 1998-01-30
PT102027B (en) 1999-04-30
ES2138537A1 (en) 2000-01-01
GB9615276D0 (en) 1996-09-04
AT412872B (en) 2005-08-25
ATA122697A (en) 2005-01-15
MX9705481A (en) 1998-08-30

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