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Synthesis 2005(13): 2119-2121
DOI: 10.1055/s-2005-869984
DOI: 10.1055/s-2005-869984
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York
The First Synthesis of Novel (1-Alkoxycarbonyloxyethylidene)-1,1-bisphosphonic Acid Derivatives Taking Advantage of the Rearrangement Characteristic of the Tetramethyl Ester of Etidronate
Weitere Informationen
Received
21 February 2005
Publikationsdatum:
27. Juni 2005 (online)
Publikationsverlauf
Publikationsdatum:
27. Juni 2005 (online)
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Abstract
A novel method to (1-alkoxycarbonyloxyethylidene)-1,1-bisphosphonic acid derivatives 1a-c, where R = Et, Pr, i-Bu, from the tetramethyl ester of etidronate (3) and a novel alkoxycarbonyl chloride has been developed; products were isolated in reasonable yields (60-88%). The easy rearrangement characteristic of etidronate tetramethyl ester to tetraalkyl phosphonophosphate was advantageous.
Key words
bisphosphonate - etidronate - ester - 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. Obst. Gynecol. 1996, 88: 431 -
2a
Szajnman SH.Montalvetti A.Wang Y.Docampo R.Rodriguez JB. Bioorg. Med. Chem. Lett. 2003, 13: 3231 -
2b
Szajnman SH.Bailey BN.Docampo R.Rodriguez JB. Bioorg. Med. Chem. Lett. 2001, 11: 789 -
2c
Martin MB.Sanders JM.Kendrick H.Luca-Fradley K.Lewis JC.Grimley JS.Van Brussel EM.Olsen JR.Meints GA.Burzynska A.Kafarski P.Croft SL.Oldfield E. J. Med. Chem. 2002, 45: 2904 -
2d
Garzoni LR.Caldera A.Nazareth L.Meirelles M.Castro SL.Docampo R.Meints GA.Oldfield E.Urbina JA. Int. J. Antimicrob. Agents 2004, 23: 273 -
2e
Garzoni LR.Waghabi MC.Baptista MM.Castro SL.Nazareth L.Meirelles M.Britto CC.Docampo R.Oldfield E.Urbina JA. Int. J. Antimicrob. Agents 2004, 23: 286 -
3a
Vepsäläinen JJ. Curr. Med. Chem. 2002, 9: 1201 -
3b
Lin JH. Bone 1996, 18: 75 -
3c
Recker RR.Saville PD. Toxicol. Appl. Pharmacol. 1973, 24: 580 -
4a
Turhanen PA.Niemi R.Peräkylä M.Järvinen T.Vepsäläinen JJ. Org. Biomol. Chem. 2003, 3223 -
4b
Ahlmark M.Vepsäläinen J.Taipale H.Niemi R.Järvinen T. J. Med. Chem. 1999, 42: 1473 -
4c
Niemi R.Vepsäläinen J.Taipale H.Järvinen T. J. Med. Chem. 1999, 42: 5053 -
4d
Niemi R.Turhanen P.Vepsäläinen J.Taipale H.Järvinen T. Eur. J. Pharm. Sci. 2000, 11: 173 -
4e
Turhanen PA.Ahlgren MJ.Järvinen T.Vepsäläinen JJ. Synthesis 2001, 633 -
5a
Li Z.Bithe P.Lang SA.Lin Y.-I. Bioorg. Med. Chem. Lett. 1997, 7: 2909 -
5b
Vigroux A.Bergon M. Bioorg. Med. Chem. Lett. 1995, 5: 427 -
6a
Pudovik AN.Konovalova IV. J. Gen. Chem. USSR 1963, 33: 91 -
6b
Pudovik AN.Gazizov TKh. J. Gen. Chem. USSR 1968, 33: 139 -
6c
Prentice JB.Quimby OT.Grabenstetter RJ.Nicholson DA. J. Am. Chem. Soc. 1972, 94: 6119 -
6d
Turhanen PA.Vepsäläinen JJ. Synthesis 2004, 992 -
6e
Chopard PA. Helv. Chim. Acta 1967, 50: 1021 -
6f
Ruel R.Bouvier J.-P.Young RN. J. Org. Chem. 1995, 60: 5209 -
6g
Guenin E.Degache E.Liquier J.Lecouvey M. Eur. J. Org. Chem. 2004, 2983 -
7a
Fitch SJ.Moedritzer K. J. Am. Chem. Soc. 1962, 84: 1876 -
7b
Nicholson DA.Vaughn H. J. Org. Chem. 1971, 36: 3843 -
7c
Ruel R.Bouvier J.-P.Young RN. J. Org. Chem. 1995, 60: 5209 -
7d
Tromelin A.El Manouni D.Burgada R. Phosphorus Sulfur Relat. Elem. 1986, 27: 301 - 8
Turhanen PA.Ahlgren MJ.Järvinen T.Vepsäläinen JJ. Phosphorus, Sulfur Silicon Relat. Elem. 2001, 170: 115 -
9a
Mc Kenna CE.Shen P. J. Org. Chem. 1981, 46: 4573 -
9b
Vaghefi MM.Bernacki RJ.Hennen WJ.Robins RK. J. Med. Chem. 1987, 30: 1391 -
9c
Nguyen LM.Niesor E.Bentzen CL. J. Med. Chem. 1987, 30: 1426 -
9d
Ebetino FH.Degenhardt CR.Jamieson LA.Burdsall DC. Heterocycles 1990, 30: 855 -
9e
Nugent RA.Murphy M.Schlachter ST.Dunn CJ.Smith RJ.Staite ND.Galinet LA.Shields SK.Aspar DG.Richard KA.Rohloff NA. J. Med. Chem. 1993, 36: 134