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Arzneimittelforschung 2006; 56(2): 136-151
DOI: 10.1055/s-0031-1296801
Stampidine
Editio Cantor Verlag Aulendorf (Germany)

Large-Scale Synthesis and Formulation of GMP-Grade Stampidine, a New Anti-HIV Agent

Darin DuMez
1   Parker Hughes Institute, Roseville, Minnesota, USA
2   Paradigm Pharmaceuticals, St. Paul, Minnesota, USA
,
Taracad K. Venkatachalam
1   Parker Hughes Institute, Roseville, Minnesota, USA
2   Paradigm Pharmaceuticals, St. Paul, Minnesota, USA
,
Fatih M. Uckun
1   Parker Hughes Institute, Roseville, Minnesota, USA
2   Paradigm Pharmaceuticals, St. Paul, Minnesota, USA
3   Ikaros Enterprises, Hudson, Wisconsin, USA
› Author Affiliations
Further Information

Publication History

Publication Date:
23 December 2011 (online)

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Summary

The arylphosphoramidate derivative of stavudine (STV, d4T, 2',3'-didehydro-3'-deoxythymidine, CAS 3056-17-5), stampidine (STAMP, DDE-113, HI-113, N-[p-(4-bromophenyl)-2',3'-didehydro-3'-deoxy-5'-thymidylyl]-L-alanine methyl ester, CAS 217178-62-6), is a novel anti-HIV agent. STAMP was prepared under current Good Manufacturing Practice (cGMP) conditions on the scale of kilograms. Solid STAMP was subsequently formulated as a capsule under GMP conditions for oral administration.

Zusammenfassung

Synthese und Formulierung von Stampidin, einem neuen Anti-HIV-Wirkstoff, im großen Maßstab und in GMP-Qualität

Stampidin (STAMP, DDE-113, HI-113, N-[p-(4-Bromphenyl)-2',3'-didehydro-3'-deoxy-5'-thymidylyl]-L-alanin-methylester, CAS 217178-62-6) ist ein Arylphosphat-Derivat von Stavudin (STV, d4T, 2',3'-Didehydro-3'-deoxythymidin, CAS 3056-17-5), das als neuer Anti-HIV-Wirkstoff entwickelt wird. Kilogramm-Mengen von STAMP wurden entspechend den GMP-Bedingungen hergestellt, ebenso wurde festes STAMP in Kapseln für die orale Verabreichug formuliert.

Key words

Anti-HIV agents - Antiretroviral therapy - N-[p-(4-Bromophenyl)-2',3'-didehydro-3'-deoxy-5'-thymidylyl]-L-alanine methyl ester - CAS 3056-17-5 - CAS 217178-62-6 - DDE-113 - HI-113 - Stampidine, formulation, GMP, synthesis - Stavudine