ES2572380T3 - Procedimiento para la preparación de cladribina - Google Patents
Procedimiento para la preparación de cladribinaInfo
- Publication number
- ES2572380T3 ES2572380T3 ES10809432T ES10809432T ES2572380T3 ES 2572380 T3 ES2572380 T3 ES 2572380T3 ES 10809432 T ES10809432 T ES 10809432T ES 10809432 T ES10809432 T ES 10809432T ES 2572380 T3 ES2572380 T3 ES 2572380T3
- Authority
- ES
- Spain
- Prior art keywords
- formula
- anomer
- cladribine
- sir1r2r3
- isolated
- 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.)
- Active
Links
- PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 title abstract 3
- 229960002436 cladribine Drugs 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 2
- 239000008241 heterogeneous mixture Substances 0.000 abstract 2
- 239000011541 reaction mixture Substances 0.000 abstract 2
- PDWIQYODPROSQH-PYHARJCCSA-N 2-deoxy-D-ribofuranose Chemical compound OC[C@H]1OC(O)C[C@@H]1O PDWIQYODPROSQH-PYHARJCCSA-N 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract 1
- 239000007848 Bronsted acid Substances 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000008878 coupling Effects 0.000 abstract 1
- 238000010168 coupling process Methods 0.000 abstract 1
- 238000005859 coupling reaction Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 230000001376 precipitating effect Effects 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
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
- C07H19/173—Purine radicals with 2-deoxyribosyl as the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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)
- Saccharide Compounds (AREA)
Abstract
Un procedimiento para hacer la cladribina de fórmula I**Fórmula** , que comprende: a) acoplar un compuesto de fórmula II**Fórmula** en donde cada uno de R1, R2 y R3 es independientemente alquilo, alquenilo, alquinilo o arilo, x es 0, 1 o 2, y es 2, 1 o 0, y R4 es hidrógeno o SiR1R2R3, con la condición de que cuando x es 2, y es 0, R4 es SiR1R2R3, con una 2-desoxiribofuranosa protegida de fórmula III**Fórmula** en donde cada uno de R6 y R7 es independientemente un grupo protector de hidroxilo, y R5 es un grupo lábil, en un disolvente orgánico y en presencia de un ácido de BrØnsted o ácido de Lewis basado en ácido sulfónico, para obtener una mezcla de reacción que comprende un anómero ß de fórmula IV**Fórmula** en donde x' es 0, 1 o 2, y' es 2, 1 o 0; b) precipitar selectivamente el anómero ß de fórmula IV de la mezcla de reacción para obtener una mezcla heterogénea en presencia de MeCN; c) aislar el anómero ß de fórmula IV precipitado de la mezcla heterogénea para obtener el anómero ß de fórmula IV aislado y sustancialmente enriquecido; y d) convertir el anómero ß de fórmula IV aislado y sustancialmente enriquecido en cladribina.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23468309P | 2009-08-18 | 2009-08-18 | |
| PCT/CN2010/001249 WO2011020298A1 (en) | 2009-08-18 | 2010-08-18 | Process for the preparation of cladribine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2572380T3 true ES2572380T3 (es) | 2016-05-31 |
Family
ID=43605867
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10809432T Active ES2572380T3 (es) | 2009-08-18 | 2010-08-18 | Procedimiento para la preparación de cladribina |
Country Status (5)
| Country | Link |
|---|---|
| US (2) | US8232387B2 (es) |
| EP (2) | EP2467391B1 (es) |
| ES (1) | ES2572380T3 (es) |
| TW (1) | TWI399381B (es) |
| WO (1) | WO2011020298A1 (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014068589A2 (en) * | 2012-10-29 | 2014-05-08 | Biophore India Pharmaceuticals Pvt. Ltd. | Novel process for the preparation of (1-{9-[(4s, 2r, 3r, 5r)-3, 4-dihydroxy-5-(hydroxymethyl) oxolan-2-yl)-6-aminopurin-2-yl} pyrazole-4-yl)-n-methylcarboxamide |
| DE102023123718A1 (de) | 2023-09-04 | 2025-03-06 | CHIRACON Pharma GmbH | Verfahren zur Herstellung von Nukleosiden |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4760137A (en) | 1984-08-06 | 1988-07-26 | Brigham Young University | Method for the production of 2'-deoxyadenosine compounds |
| CA1269659A (en) | 1984-08-06 | 1990-05-29 | Brigham Young University | Method for the production of 2'-deoxyadenosine compounds |
| US6252061B1 (en) * | 1998-03-23 | 2001-06-26 | Reliable Biopharmaceutical, Inc. | Process for the production of 2-halo-6-aminopurine derivatives |
| WO2000064918A1 (en) | 1999-04-28 | 2000-11-02 | Sterrenbeld Biotechnologie North America, Inc. | METHOD FOR THE PRODUCTION OF 2-CHLORO-2'-DEOXYADENOSINE (CLADRIBINE) AND ITS 3,5-DI-O-p-TOLUOYL DERIVATIVE |
| US20020052491A1 (en) * | 1999-04-28 | 2002-05-02 | Szepsel Gerszberg | Method for the production of 2-chloro-2' -deoxyadenosine (cladribine) and its 3,5-di-O-p-toluoyl derivative |
| US6680382B2 (en) * | 2001-08-02 | 2004-01-20 | Ilex Products, Inc. | Process for preparing purine nucleosides |
| US6884880B2 (en) | 2002-08-21 | 2005-04-26 | Ash Stevens, Inc. | Process for the preparation of 9-β-anomeric nucleoside analogs |
| CA2653247C (en) * | 2005-06-14 | 2012-12-18 | Brigham Young University | Methods for selective n-9 glycosylation of purines |
| SI1932918T1 (sl) * | 2006-12-15 | 2010-02-26 | Explora Lab Sa | Postopek izdelave kladribina |
| CN102209467B (zh) * | 2008-10-03 | 2014-03-12 | 台湾神隆股份有限公司 | 地西他滨(Decitabine)的合成 |
-
2010
- 2010-08-17 US US12/857,939 patent/US8232387B2/en active Active
- 2010-08-17 TW TW099127486A patent/TWI399381B/zh active
- 2010-08-18 EP EP10809432.7A patent/EP2467391B1/en active Active
- 2010-08-18 EP EP14173103.4A patent/EP2891660A1/en not_active Withdrawn
- 2010-08-18 ES ES10809432T patent/ES2572380T3/es active Active
- 2010-08-18 WO PCT/CN2010/001249 patent/WO2011020298A1/en not_active Ceased
-
2012
- 2012-03-26 US US13/429,827 patent/US8338586B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| TW201121988A (en) | 2011-07-01 |
| WO2011020298A1 (en) | 2011-02-24 |
| US8338586B2 (en) | 2012-12-25 |
| EP2467391B1 (en) | 2016-04-27 |
| EP2467391A4 (en) | 2013-07-03 |
| EP2891660A1 (en) | 2015-07-08 |
| US20110046363A1 (en) | 2011-02-24 |
| EP2467391A1 (en) | 2012-06-27 |
| US8232387B2 (en) | 2012-07-31 |
| US20120197010A1 (en) | 2012-08-02 |
| TWI399381B (zh) | 2013-06-21 |
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