Optimization, continuation and lack of the one-step diphosphorylation reaction. Assay of modification of the tetraethyl(pyrrolidine-2,2-diyl)bisphosphonate
Olive, Gilles; Jacques, Alain
2003 • In Phosphorus, Sulfur and Silicon and the Related Elements, 178 (1), p. 33-46
[en] The optimization of the one-step diphosphorylation reaction is reported. The synthesis of new ®-aminobisphosphonates with four- and sixmembered rings and acyclic species with several substituents on the nitrogen atom and on the carbon atom bearing the two phosphorus atoms is described.
Optimization, continuation and lack of the one-step diphosphorylation reaction. Assay of modification of the tetraethyl(pyrrolidine-2,2-diyl)bisphosphonate
Publication date :
2003
Journal title :
Phosphorus, Sulfur and Silicon and the Related Elements
G. Sturtz and H. Couthon, C. R. Acad. Sc. Paris, 316 (Serie II), 181 (1993).
A. Ebrahimpour, F. H. Ebetino, G. Sethuraman, and G. H. Nancollas, Determination of Solubility and Calcium Ion Stability Constants of a Phosphonoalkylphosphinate (PAP) and Bisphosphonates (BPs) Such as EHDP, Risedronate, Alendronate, 3-pic AMBP, and 3-pic AMPMP, edited by Z. Amjad (Plenum Press, New York, 1995), p. 295.
W. Plöger, M. Schmidt-Dunker, and C. Gloxhuber, US PAT. 3,988,443 (1976).
D. Nelson and H. Smitherman, US PAT. WO 92/00721 (1992).
M. Nakamura, T. Ando, M. Abe, K. Kumagai, and Y. Endo, Br. J. Pharmacol., 119, 2O5 (1996).
J. G. Slatter, K. L. Feenstra, M. J. Hauer, D. A. Kloosterman, A. H. Parton, P. E. Sanders, G. Scott, and W. Speed, Drug Metab. Dispos., 24, 65 (1996).
J. P. Räsänen, E. Pohjala, H. Nikander, and T. A. Pakkanen, J. Phys. Chem., 100, 8230 (1996).
C. Dufau and G. Sturtz, Phosphorus, Sulfur, Silicon Relat. Elem., 69, 93 (1992).
J. H. Lin, Bone, 18, 75 (1996).
F. Hosain, R. P. Spencer, H. M. Couthon, and G. L. Sturtz, J. Nucl. Med., 37, 105 (1996).
D. V. Griffiths, J. M. Hughes, J. W. Brown, J. C. Caesar, S. P. Swetnam, S. A. Cumming, and J. D. Kelly, Tetrahedron, 53, 17815 (1997).
R. K. Harris, P. Jackson, L. H. Merwin, B. J. Say, and G. Hägele, J. Chem. Soc., Faraday Trans. 1, 84, 3649 (1988).
R. T. Chlebowski and A. McTiernan, J. Clin. Oncol., 17, 130 (1999).
M. Mimura, M. Hayashida, K. Nomiyama, S. Ikegami, Y. Iida, M. Tamura, Y. Hiyama, and Y. Ohishi, Chem. Pharm. Bull., 41, 1971 (1993).
T. Yokomatsu, Y. Yoshida, N. Nakabayashi, and S. Shibuya, J. Org. Chem., 59, 7562 (1994).
F. Cheng, X. Yang, C. Fan, and H. Zhu, Tetrahedron, 57, 7331 (2001).
R. A. Nugent, M. Murphy, S. T. Schlachter, C. J. Dunn, R. J. Smith, N. D. Staite, L. A. Galinet, S. K. Shields, D. G. Aspar, K. A. Richard, and N. A. Rohloff, J. Med. Chem., 36, 134 (1993).
J. C. Brelière, X. Edmonds-Alt, and G. Garcia, Eur. Pat. 100 718; Chem. Abstr., 1984, 100, 192078j (1983).
H.-J. Cristau, C. Brahic, and J.-L. Pirat, Tetrahedron, 57, 9149 (2001).
D. Kantoci, J. K. Denike, and W. J. Wechter, Synth. Commun., 26, 2037 (1996).
K. Fisher, F. Woolard, M. Leadbetter, and J. Gerdes, US PAT. WO 96/31124 (1996).
T. H. Cromartie, K. J. Fisher, and J. N. Grossman, Pestic. Biochem. Physiol., 63, 114 (1999).
D. Q. Qian, X. D. Shi, R. Z. Cao, and L. Z. Liu, Heteroat. Chem., 10, 271 (1999).
J. Ohanessian, D. Avenel, D. El Manouni, and M. Benramdane, Phosphorus, Sulfur; Silicon Relat. Elem., 129, 99 (1997).
L. Lemée, M. Gulea, M. Saquet, S. Masson, and N. Collignon, Heteroat. Chem., 10, 281 (1999).
D. C. Stepinski, D. W. Nelson, P. R. Zalupski, and A. W. Herlinger, Tetrahedron, 57, 8637 (2001).
A. Rockenbauer, A. Mercier, F. Le Moigne, G. Olive, and P. Tordo, J. Phys. Chem. A, 101, 7965 (1997).
G. Olive, F. Le Moigne, A. Mercier, A. Rockenbauer, and P. Tordo, J. Org. Chem., 63, 9095 (1998).
F. Palacios, M. J. Gil, E. Martínez de Marigorta, and M. Rodríguez, Tetrahedron, 56, 6319 (2000).
G. Sturtz, H. Couthon, O. Fabulet, M. Mian, and S. Rosini, Eur. J. Med. Chem., 28, 899 (1993).
N. Kreutzkamp and G. Cordes, Ann., 623, 103 (1959).
L. Maier, Phosphorus and Sulfur, 11, 311 (1981).
A. Köckritz, G. Röhr, and M. Schnell, Phosphorus, Sulfur, Silicon Relat. Elem., 63, 95 (1991).
D. Q. Qian, X. D. Shi, R. Z. Cao, and L. Z. Liu, Tet. Lett., 38, 6245 (1997).
G. Olive, F. Le Moigne, A Mercier, and P. Tordo, Synth. Commun., 30, 629 (2000).
G. R. F. M. Olive, Ph.D. Thesis, Université d'Aix, Marseille III (1998).
E. W. Petillo and R. Spitzmiller, Tetrahedron Lett., 51, 4929 (1979).
H. Gross, B. Costisella, and L. Brennecke, Phosphorus, 4, 241 (1974).
G. Olive and M. H. P. van Genderen, Magn. Res. Chem., 38, 379 (2000).
G. M. Blackburn, D. Brown, S. J. Martin, and M. J. Parratt, J. Chem. Soc., Perkin Trans. 1, 181 (1987).
E. E. Nifant'ev, L. M. Runova, T. G. Shestakova, E. V. Bogatyreva, and V. I. Ronkov, Zh. Obshch. Khim., 50, 304 (1980).
U. Jahn, J. Andersch, and W. Schroth, Synthesis, 573 (1997).
J. J. Vepsäläinen, J. Kivikoski, M. Ahlgén, H. E. Nupponen, and E. K. Pohjalad, Tetrahedron, 51, 6805 (1995).
H. Gross and B. Costisella, J. Prakt. Chem., 328, 231 (1986).
S. Pietri, M. Miollan, S. Martel, F. Le Moigne, B. Blaive, and M. Culcasi, J. Biol. Chem., 275, 19505 (2000).