Bisphosphonate prodrugs: Synthesis and in vitro evaluation of novel clodronic acid dianhydrides as bioreversible prodrugs of clodronate

Journal of Medicinal Chemistry

Volumn 42, Issue 8, 1999, Pages 1473-1476

  Ahlmark, Marko ^a   Vepsäläinen, Jouko ^a   Taipale, Hannu ^a   Niemi, Riku ^a   Järvinen, Tomi ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

BISPHOSPHONIC ACID DERIVATIVE; CLODRONIC ACID; PRODRUG;

ARTICLE; DRUG BIOAVAILABILITY; DRUG EFFECT; DRUG SOLUBILITY; DRUG SYNTHESIS; DRUG USE; HUMAN; LIPOPHILICITY; OSTEOPOROSIS;

ANHYDRIDES; CLODRONIC ACID; HUMANS; HYDROLYSIS; KINETICS; PRODRUGS;

EID: 0344731435     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9810809     Document Type: Article

References (19)

1. Fleisch, H. Bisphosphonates in Bone Disease: From the Laboratory to the Patient; The Parthenon Publishing Group Inc.: New York, 1995.
2. Fleisch, H. Bisphosphonates: Pharmacology and use in the Treatment of Tumour-Induced Hypercalcaemic and Metastatic Bone Disease. Drugs 1991, 42, 919-944.
3. Papapoulos, S. E.; Landman, J. O.; Bijvoet, O. L. M.; Löwik, C. W. G. M.; Valkema, R.; Pauwels, E. K. J.; Vermeij, P. The Use of Bisphosphonates in the treatment of Osteoporosis. Bone 1992, 13, S41-S49.
4. Yates, J.; Rodan, A. Alendronate and Osteoporosis. DDT 1998, 3, 69-78.
5. Socrates, E.; Papapoulos, M. D. The Role of bisphosphonates in the Prevention and Treatment of Osteoporosis. Am. J. Med. 1993, 95, 48S-52S.
6. Giannini, S.; D'Angelo, A.; Sartori, L.; Passeri, G.; Carbonare, L. D.; Crepaldi, C. Continuous and Cyclical Clodronate Therapies and Bone Density in Postmenopausal Bone Loss. Obst. Gynecol. 1996, 88, 431-436.
7. Salo, J.; Lehenkari, P.; Mulari, M.; Metsikkö, K.; Väänänen, H. K. Removal of Osteoclast Bone Resorption Products by Transcytosis. Science 1997, 276, 270-273.
8. Hannuniemi, R.; Laurén, L.; Puolijoki, H. Clodronate: an Effective Agent for the Treatment of Increased Bone Resorption. Drugs Today 1991, 27, 375-389.
9. Yakatan, G. J.; Poynor, W. J.; Talbert, R. L.; Floyd, B. F.; Slough, C. L.; Ampulski, R. S.; Benedict, J. J. Clodronate Kinetics and Bioavailability. Clin. Pharmacol. Ther. 1982, 31, 402-410.
10. Pentikäinen, P. J.; Elomaa, I.; Nurmi, A.-K.; Kärkkäinen, S. Pharmacokinetics of Clodronate in Patients with Metastatic Breast Cancer. Int. J. Clin. Pharmacol. Ther. Toxicol. 1989, 27, 222-228.
11. Vepsäläinen, J.; Vainiotalo, P.; Nupponen, H.; Pohjala, E. Preparation and Identification of Tetraamide Esters of Methylene-and (Dichloromethylene)bisphosphonates. Acta Chem. Scand. 1997, 51, 932-937.
12. McKenna, C. E.; Khawli, L. A.; Ahmad, W.-Y.; Pham, P.; Bongartz, J.-P. Synthesis of α-Halogenated Methanediphosphonates. Phosp. Sulf. 1988, 37, 1-12.
13. Ahlmark, M. J.; Vepsäläinen, J. J. Strategies for the Selective Synthesis of Monosubstituted (dichloromethylene)bisphosphonate Esters. Tetrahedron 1997, 53, 16153-16160.
14. Niemi, R.; Taipale, H.; Ahlmark, M.; Vepsäläinen, J.; Järvinen, T. Simultaneous Determination of Clodronate and its Partial Ester Derivatives by Ion-Pair Reversed-Phase High-Performance Liquid Chromatography Coupled with Evaporative Light-Scattering Detection. J. Chromatogr. B 1997, 701, 97-102.
15. Lin, J. H. Bisphosphonates: a Review of Their Pharmacokinetic Properties. Bone 1996, 18, 75-85.
16. Räsänen, J. P.; Pohjala, E.; Nikander, H.; Pakkanen, T. P. Ab Initio Studies on Organophosphorus Compounds. 5. Interactions of Dianionic Bisphosphonate Compounds with Magnesium and Calcium. J. Phys. Chem. 1996, 100, 8230-8239.
17. Björkroth, J.-P.; Pakkanen, T. A.; Lindroos, J. Comparative Molecular Field Analysis of Some Clodronic Acid Esters. J. Med. Chem. 1991, 34, 2338-2343.
18. 14C-Labeled Clodronate. J. Labeled Compd. Radiopharm. 1991, 29, 1191-1196.
19. Vepsäläinen, J.; Nupponen, H.; Pohjala, E.; Ahlgren, M. Bisphosphonic Compounds. Part 3. Preparation and identification of Tetraalkyl Methylene-and (α-Halomethylene)bisphosphonates by Mass Spectrometry, NMR Spectroscopy and X-ray Crystallography. J. Chem. Soc., Perkin Trans. 2 1992, 835-842.