Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2004(7): 0992-0994
DOI: 10.1055/s-2004-822345
DOI: 10.1055/s-2004-822345
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
Strategies for the Preparation of (1-Acetyloxyethylidene)-1,1-bisphosphonic Acid Derivatives
Further Information
Received
17 February 2004
Publication Date:
25 April 2004 (online)
Publication History
Publication Date:
25 April 2004 (online)
Abstract
The novel strategies for the synthesis of acetylated etidronic acid derivatives were investigated. (1-Acetyloxyethylidene)-1,1-bisphosphonic acid and its P,P′-dimethyl, trimethyl and tetramethyl esters were prepared in high 81-100% yields.
Key words
bisphosphonate - etidronate - partial esters - synthesis - prodrug
-
1a
Fleisch H. Bisphosphonates in Bone Disease: From the Laboratory to the Patient The Parthenon Publishing Group Inc.; New York: 1995. -
1b
Papapoulos SE.Landman JO.Bijvoet OLM.Löwik CWGM.Valkema R.Pauwels EKJ.Vermeij P. Bone 1992, 13: S41 -
1c
Yates AJ.Rodan GA. Drug Discovery Today 1998, 3: 69 -
1d
Socrates E.Papapoulos MD. Am. J. Med. 1993, 95: 48S -
1e
Giannini S.D’Angelo A.Sartori L.Passeri G.Garbonare LD.Crebaldi C. Obstet. Gynecol. 1996, 88: 431 -
2a
Vepsäläinen JJ. Curr. Med. Chem. 2002, 9: 1075 -
2b
Lin JH. Bone 1996, 18: 75 -
2c
Recker RR.Saville PD. Toxicol. Appl. Pharmacol. 1973, 24: 580 -
3a
Sinkkula AA.Yalkowsky SH. J. Pharm. Sci. 1975, 64: 181 -
3b
Stella VJ.Charman WNA.Naringregar VH. Drugs 1985, 29: 455 -
3c
Balant LP.Doelker E.Buri P. Eur. J. Drug Metab. Pharmacokinet. 1990, 15: 143 -
3d
Waller DG.George CF. Br. J. Clin. Pharmacol. 1989, 28: 497 -
4a
Turhanen PA.Niemi R.Peräkylä M.Järvinen T.Vepsäläinen JJ. Org. Biomol. Chem. 2003, 1: 3223 -
4b
Niemi R.Turhanen P.Vepsäläinen J.Taipale H.Järvinen T. Eur. J. Pharm. Sci. 2000, 11: 173 -
4c
Turhanen PA.Ahlgren MJ.Järvinen T.Vepsäläinen JJ. Phosphorus, Sulfur Silicon Relat. Elem. 2001, 170: 115 -
4d
Turhanen PA.Ahlgren MJ.Järvinen T.Vepsäläinen JJ. Synthesis 2001, 4: 633 - 5
Prentice JB.Quimby OT.Grabenstetter RJ.Nicholson DA. J. Am. Chem. Soc. 1972, 94: 6119