Nucleophilic Addition of Bisulfite Ion to Prostaglandins E2 and A2: Implication in Aqueous Stability

Journal of Pharmaceutical Sciences - Tập 66 - Trang 149-154 - 1977
M.J. Cho1, W.C. Krueger1, T.O. Oesterling1
1Pharmacy Research, The Upjohn Company, Kalamazoo, MI 49001

Tài liệu tham khảo

Bergstrom, 1967, Science, 157, 382, 10.1126/science.157.3787.382 Oesterling, 1972, J. Pharm. Sci, 61, 1861, 10.1002/jps.2600611202 Weeks, 1972, Ann. Rev. Pharmacol., 12, 317, 10.1146/annurev.pa.12.040172.001533 Hinman, 1972, Ann. Rev. Biochem., 41, 161, 10.1146/annurev.bi.41.070172.001113 Andersen, 1974, Arch. Intern. Med., 133, 30, 10.1001/archinte.1974.00320130032004 Bundy, 1972, Ann. Rev. Med. Chem., 2, 157 Axen, 1973, vol. 1 Weinshenker, 1973, vol. 1 1972 Murnaghan, 1974, J. Obstet. Gynaecol. Br. Commonw., 81, 141, 10.1111/j.1471-0528.1974.tb00433.x Miller, 1974, J. Obstet. Gynaecol. Br. Commonw., 81, 706, 10.1111/j.1471-0528.1974.tb00545.x Elder, 1974, Prostaglandins, 6, 427, 10.1016/0090-6980(74)90018-5 Bergstrom, 1967, Prostaglandins, 21 Karim, 1968, Eur. J. Pharmacol., 4, 416, 10.1016/0014-2999(68)90028-9 Andersen, 1969, J. Lipid Res., 10, 320, 10.1016/S0022-2275(20)43090-1 Oesterling, 1970, 44 Monkhouse, 1973, J. Pharm. Sci., 62, 576, 10.1002/jps.2600620406 Thompson, 1973, J. Pharm. Sci., 62, 1738, 10.1002/jps.2600621044 Daniels, 1968, J. Am. Chem. Soc., 90, 5894, 10.1021/ja01023a041 Bell, 1966, J. Chem. Soc. (B), 241 Pike, 1969, J. Org. Chem., 34, 3552, 10.1021/jo01263a071 Fedor, 1971, J. Am. Chem. Soc., 93, 985, 10.1021/ja00733a034 Hupe, 1973, J. Am. Chem. Soc., 95, 2260, 10.1021/ja00788a027 Schroeter, 1966, 273 Cho, 1974, J. Am. Chem. Soc., 96, 1843, 10.1021/ja00813a032 Pitman, 1974, J. Am. Chem. Soc., 96, 1840, 10.1021/ja00813a031 March, 1968, 568 Crabbé, 1974, Tetrahedron, 30, 1979, 10.1016/S0040-4020(01)97328-4 Petrenko-Kritschenko, 1906, Chem. Ber., 39, 1452, 10.1002/cber.19060390255 Grudzinskas, 1973, Tetrahedron Lett., 141, 10.1016/S0040-4039(01)95599-6 Bundy, 1971, Ann. N.Y. Acad. Sci., 180, 76, 10.1111/j.1749-6632.1971.tb53186.x Sander, 1968, J. Am. Chem. Soc., 90, 6154, 10.1021/ja01024a038 Fife, 1961, J. Phys. Chem., 65, 1079, 10.1021/j100824a525 Crabbé, 1965, 191 A. G. Long and L. J. Wyman (to Glaxo Labs), U.S. pat. 2,908,695 (Oct. 13,1959); through Ref. 24, p. 111. Smith, 1972, J. Pharm. Sci., 61, 708, 10.1002/jps.2600610508 Higuchi, 1965, vol. 4, 117 Connors, 1966, J. Pharm. Sci., 55, 772, 10.1002/jps.2600550805 Higuchi, 1969, J. Pharm. Sci., 58, 661, 10.1002/jps.2600580603 Mader, 1970, Crit. Rev. Anal. Chem., 1, 193, 10.1080/10408347008085634 Meier, 1965, J. Pharm. Sci., 54, 1183, 10.1002/jps.2600540819 Higuchi, 1953, J. Am. Pharm. Assoc., Sci. Ed., 42, 132, 10.1002/jps.3030420306 Rowe, 1972, J. Pharm. Sci., 61, 2630, 10.1002/jps.2600610523 Mulley, 1964, vol. 1, 86 Roseman, 1973, J. Pharm. Sci., 62, 1680, 10.1002/jps.2600621021 Pasto, 1969, 393 Higuchi, 1960, J. Am. Chem. Soc., 82, 1904, 10.1021/ja01493a018 D. C. Monkhouse (to Pfizer), U.S. pat. 3,851,052 (Nov. 26, 1974). Hine, 1970, J. Org. Chem., 35, 2769, 10.1021/jo00833a065 Bourne, 1974, J. Pharm. Sci., 63, 865, 10.1002/jps.2600630612