ES2138537A1 - Procedimiento para la preparacion de los compuestos antivirales penciclovir y famciclovir. - Google Patents
Procedimiento para la preparacion de los compuestos antivirales penciclovir y famciclovir.Info
- Publication number
- ES2138537A1 ES2138537A1 ES009701615A ES9701615A ES2138537A1 ES 2138537 A1 ES2138537 A1 ES 2138537A1 ES 009701615 A ES009701615 A ES 009701615A ES 9701615 A ES9701615 A ES 9701615A ES 2138537 A1 ES2138537 A1 ES 2138537A1
- Authority
- ES
- Spain
- Prior art keywords
- carboxy
- penciclovir
- famciclovir
- hydrogen
- procedure
- 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
Links
- JNTOCHDNEULJHD-UHFFFAOYSA-N Penciclovir Chemical compound N1C(N)=NC(=O)C2=C1N(CCC(CO)CO)C=N2 JNTOCHDNEULJHD-UHFFFAOYSA-N 0.000 title abstract 4
- 229960004396 famciclovir Drugs 0.000 title abstract 4
- GGXKWVWZWMLJEH-UHFFFAOYSA-N famcyclovir Chemical compound N1=C(N)N=C2N(CCC(COC(=O)C)COC(C)=O)C=NC2=C1 GGXKWVWZWMLJEH-UHFFFAOYSA-N 0.000 title abstract 4
- 229960001179 penciclovir Drugs 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 3
- 230000000840 anti-viral effect Effects 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 title abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 10
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 abstract 8
- 229910052739 hydrogen Chemical group 0.000 abstract 5
- 239000001257 hydrogen Chemical group 0.000 abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 4
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract 3
- UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 abstract 2
- 150000003254 radicals Chemical group 0.000 abstract 2
- MWBWWFOAEOYUST-UHFFFAOYSA-N 2-aminopurine Chemical compound NC1=NC=C2N=CNC2=N1 MWBWWFOAEOYUST-UHFFFAOYSA-N 0.000 abstract 1
- 238000006114 decarboxylation reaction Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 1
Landscapes
- 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.
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 true ES2138537A1 (es) | 2000-01-01 |
| ES2138537B1 ES2138537B1 (es) | 2000-11-16 |
Family
ID=10797241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES9701615A Expired - Fee Related ES2138537B1 (es) | 1996-07-20 | 1997-07-18 | Procedimiento para la preparacion de los compuestos antivirales penciclovir y famciclovir. |
Country Status (5)
| Country | Link |
|---|---|
| AT (1) | AT412872B (es) |
| ES (1) | ES2138537B1 (es) |
| GB (1) | GB9615276D0 (es) |
| GR (1) | GR1002942B (es) |
| PT (1) | PT102027B (es) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5075445A (en) * | 1983-08-18 | 1991-12-24 | Beecham Group P.L.C. | Guanine derivatives |
| WO1995028402A2 (en) * | 1994-04-19 | 1995-10-26 | Smithkline Beecham Plc | Preparation of purines |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| DE3582399D1 (de) * | 1984-09-20 | 1991-05-08 | Beecham Group Plc | Purin-derivate und ihre pharmazeutische verwendung. |
| SE8406538D0 (sv) * | 1984-12-21 | 1984-12-21 | Astra Laekemedel Ab | Novel derivatives of purine |
| DE3671227D1 (de) * | 1985-07-27 | 1990-06-21 | Beecham Group Plc | 9-substituierte guaninmonohydrate. |
| 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 |
-
1996
- 1996-07-20 GB GBGB9615276.4A patent/GB9615276D0/en active Pending
-
1997
- 1997-07-18 ES ES9701615A patent/ES2138537B1/es not_active Expired - Fee Related
- 1997-07-18 GR GR970100280A patent/GR1002942B/el not_active IP Right Cessation
- 1997-07-18 AT AT122697A patent/AT412872B/de not_active IP Right Cessation
- 1997-07-18 PT PT10202797A patent/PT102027B/pt not_active IP Right Cessation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5075445A (en) * | 1983-08-18 | 1991-12-24 | Beecham Group P.L.C. | Guanine derivatives |
| WO1995028402A2 (en) * | 1994-04-19 | 1995-10-26 | Smithkline Beecham Plc | Preparation of purines |
Non-Patent Citations (1)
| Title |
|---|
| GEEN G.R. et al., The Effect of the C-6 substituent on the regioselectivity of N-alkylation of 2-aminopurines, Tetrahedron, Vol. 46, no 19, paginas 6903-6914, 1990. * |
Also Published As
| Publication number | Publication date |
|---|---|
| MX9705481A (es) | 1998-08-30 |
| GR1002942B (el) | 1998-07-21 |
| PT102027A (pt) | 1998-01-30 |
| ATA122697A (de) | 2005-01-15 |
| ES2138537B1 (es) | 2000-11-16 |
| AT412872B (de) | 2005-08-25 |
| GB9615276D0 (en) | 1996-09-04 |
| PT102027B (pt) | 1999-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EC2A | Search report published |
Date of ref document: 20000101 Kind code of ref document: A1 Effective date: 20000101 |
|
| FD2A | Announcement of lapse in spain |
Effective date: 20180807 |