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Silyl methods for the modification of penicillin and cephalosporin (review)

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The principal pathways of modification of β-lactam antibiotics by means of silyl methods, including silylation, the preparation of N-acyl and amide analogs of penicillin and cephalosporin, the deacylation of N-protective groups, the epimerization of the side chain, the transformation of penicillin to cephalosporin, and other transformations, are examined.

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Literature cited

  1. E. H. Flynn, Cephalosporins, Chemistry and Biology, Academy of Sciences of the Latvian SSR, New York (1972).

    Google Scholar 

  2. J. H. C. Nayler, Adv. Drug Res., 7, 1 (1973).

    Google Scholar 

  3. A. K. Mukerjee and A. K. Singh, Synthesis, 9, 547 (1975).

    Google Scholar 

  4. R. J. Stoodley, Tetrahedron, 31, 2325 (1975).

    Google Scholar 

  5. B. E. Cooper, Process Biochem., 9 (1980).

  6. É Ya. Lukevits, A. E. Zablotskaya, and I. I. Solomennikova, Usp. Khim., 43, 370 (1974).

    Google Scholar 

  7. K. W. Glombitza, Lieb. Ann., 673, 166 (1964).

    Google Scholar 

  8. B. O. Sjoberg and A. B. Ekstrora, BE Patent No. 628231; Chem. Abstr., 61, 1870 (1964).

    Google Scholar 

  9. Chemie Grunenthal G.m.b.H., BE Patent No. 615344; Chem. Abstr., 59, 5173 (1963).

    Google Scholar 

  10. L. Birkofer, BE Patent No. 615401; Chem. Abstr., 59, 2826 (1963).

    Google Scholar 

  11. S. Herrling and H. Muecter, US Patent No. 3249622; Chem. Abstr., 65, 3884 (1966).

    Google Scholar 

  12. G. Palladino and E. Paolinich, GB patent No. 2001985; Chem. Abstr., 91, 211428 (1979).

    Google Scholar 

  13. T. Ishimary and Y. Codama, JA Patent No. 738690; Chem. Abstr., 80, 37131 (1974).

    Google Scholar 

  14. T. Ishimary and Y. Codama, DT Patent No. 2151531; Chem. Abstr., 77, 34502 (1972).

    Google Scholar 

  15. P. Crooij and A. Colinet, US Patent No. 3912728; Chem. Abstr., 84, 440986 (1976).

    Google Scholar 

  16. S. Herrling, DT Patent No. 2115542; Chem. Abstr., 78, 84400 (1973).

    Google Scholar 

  17. J. Werweij, DT Patent No. 2166561; Chem. Abstr., 81, 152216 (1974).

    Google Scholar 

  18. N. Asako, T. Soma, and C. Harukawa, Jpn. Patent No. 7748991; Chem. Abstr., 89, 215417 (1978).

    Google Scholar 

  19. C. A. Robinson, DT Patent No. 1931624; Chem. Abstr., 72, 43665 (1970).

    Google Scholar 

  20. T. Ishimary, Jpn. Patent No. 7612637; Chem. Abstr., 86, 121324 (1977).

    Google Scholar 

  21. S. P. A. Procter, GB Patent No. 1459807; Chem. Abstr., 87, 39508 (1977).

    Google Scholar 

  22. B. E. Cooper and D. W. Butler, DT Patent No. 2649536; Chem. Abstr., 87., 135894 (1977).

    Google Scholar 

  23. W. J. Wheeler, US Patent No. 4035361; Chem. Abstr., 87, 135371 (1977).

    Google Scholar 

  24. T. Tamura, T. Ishimary, and T. Shinuchi, Jpn. Patent No. 77125186; Chem. Abstr., 88., 170166 (1978).

    Google Scholar 

  25. M. Croci and G. Gotti, DT Patent No. 2701406; Chem. Abstr., 87., 135309 (1977).

    Google Scholar 

  26. B. G. Jackson, DT Patent No. 1942454; Chem. Abstr., 74, 125836 (1971).

    Google Scholar 

  27. C. A. Gema, DT Patent No. 2462383; Chem. Abstr., 86, 140067 (1977).

    Google Scholar 

  28. A. L. C. Palomo, DT Patent No. 2408171; Chem. Abstr., 81, 152210 (1974).

    Google Scholar 

  29. P. Renato and F. Marco, ES Patent No. 448741; Chem. Abstr., 88, 105387 (1978).

    Google Scholar 

  30. K. Ishibashi, H. Ishiguro, Y. Miyaji, and K. Moshizuki, Jpn. Patent No. 7859689; Chem. Abstr., 89, 146917 (1978).

    Google Scholar 

  31. K. Shimizy, H. Asai, and S. Kuroyanagi, Jpn. Patent No. 7882791; Chem. Abstr., 90, 103979 (1979).

    Google Scholar 

  32. L. Birkofer and A. Ritter, DT Patent No. 1770855; Chem. Abstr., 81, 13501 (1974).

    Google Scholar 

  33. P. Sieber, DT Patent No. 2706490; Chem. Abstr., 88, 23391 (1978).

    Google Scholar 

  34. F. Bortesi, S. Cavalli, and A. Mangia, J. Pharm. Sci., 66, 1767 (1977).

    Google Scholar 

  35. S. Silingardi, M. Di Bitetto, and A. Mangia, J. Pharm. Sci., 66., 1769 (1977).

    Google Scholar 

  36. H.-L. Wu, M. Masada, and T. Uno, J. Chromatogr., 137, 127 (1977).

    Google Scholar 

  37. L. Doub and J. S. Kalterbronn, US Patent No. 3948903; Chem. Abstr., 85, 21348 (1976).

    Google Scholar 

  38. H. H. Silvestri, US Patent No. 3862186; Chem. Abstr., 83, 48198 (1975).

    Google Scholar 

  39. E. Kisewetter and S. Herrling, US Patent No. 3926954; Chem. Abstr., 85, 33042 (1976).

    Google Scholar 

  40. T. Ishimary and Y. Kodama, DT Patent No. 2163514; Chem. Abstr., 79, 78862 (1973).

    Google Scholar 

  41. P. Borrevang, P. Faarup, E. Guddal, J. K. Nielsen, and H. B. Petersen, DT Patent No. 2612523; Chem. Abstr., 86, 89853 (1977).

    Google Scholar 

  42. R. Wiederkehr and H. Bickel, DT Patent No. 2636962; Chem. Abstr., 87, 85015 (1977).

    Google Scholar 

  43. B. Bouzard and A. Weber, GB Patent No. 1484120; Chem. Abstr., 88, 105365 (1978).

    Google Scholar 

  44. P. Crooij and G. Simonet, DT Patent No. 2615091; Chem. Abstr., 86, 89905 (1977).

    Google Scholar 

  45. R. D. G. Cooper, G. V. Kaiser, C. F. Murphy, E. M. van Heyningen, and J. A. Webber, DT Patent No. 1940080; Chem. Abstr., 74, 22863 (1971).

    Google Scholar 

  46. B. G. Kristensen, USSR Inventor's Certificate No. 450413; Byull. Izobret., No. 42, 154 (1974).

  47. K. Shimizu and A. Asai, Jpn. Patent No. 78124289; Chem. Abstr., 90, 152173 (1979).

    Google Scholar 

  48. K. Shimizu and H. Terai, Jpn. Patent No. 7884988; Chem. Abstr., 90, 6393 (1979).

    Google Scholar 

  49. P. W. Henniger, GB Patent No. 1339708; Chem. Abstr., 80, 95937 (1974).

    Google Scholar 

  50. P. M. Smid and J. Calter, DT Patent No. 2264602; Chem. Abstr., 81, 49675 (1974).

    Google Scholar 

  51. J. H. Sellstedt and S. C. Bell, US Patent No. 3714150; Chem. Abstr., 78, 124608 (1973).

    Google Scholar 

  52. P. W. Henniger and J. K. van der Drift, DT Patent No. 2235390; Chem. Abstr., 78, 124608 (1973).

    Google Scholar 

  53. J. H. Sellstedt, D. M. Teller, and C. J. Guinosso, US Patent No. 3720666; Chem. Abstr., 79, 5329 (1973).

    Google Scholar 

  54. P. Grooji and A. Colinet, US Patent No. 3994887; Chem. Abstr., 86, 106624 (1977).

    Google Scholar 

  55. Koninklijke Nederlandishe, DT Patent No. 2062297; Chem. Abstr., 75, 98565 (1971).

    Google Scholar 

  56. P. Borrevang, E. Guddal, H. B. Petersen, P. Faarup, and J. K. Nielsen, DT Patent No. 2364759; Chem. Abstr., 83, 10064 (1975).

    Google Scholar 

  57. E. Guddal, DT Patent No. 2626280; Chem. Abstr., 36, 140072 (1977).

    Google Scholar 

  58. P. Borrevang, P. Faarup, E. Guddal, J. K. Nielsen, and H. B. Petersen, DT Patent No. 2612523; Chem. Abstr., 86, 89853 (1977).

    Google Scholar 

  59. E. Kiesewetter and S. Herrling, US Patent No. 3926954; Chem. Abstr., 85, 33042 (1976).

    Google Scholar 

  60. J. H. Grossman and G. A. Hardcastle, DT Patent No. 2611286; Chem. Abstr., 86, 16664 (1977).

    Google Scholar 

  61. D. A. Love, GB Patent No. 1339605; Chem. Abstr., 80, 108507 (1974).

    Google Scholar 

  62. J. M. Goldman, DT Patent No. 2334343; Chem. Abstr., 80, 120917 (1974).

    Google Scholar 

  63. P. Feyen, DT Patent No. 2622456; Chem. Abstr., 88, 89622 (1978).

    Google Scholar 

  64. S. Morimoto, H. Nomura, T. Fugonono, K. Takeshi, and J. Ishigura, DT Patent No. 1966850; Chem. Abstr., 81, 136135 (1974).

    Google Scholar 

  65. J. Saikawa, S. Takano, H. Imaizumi, I. Takakura, H. Ochiaki, T. Yasuda, H. Taki, M. Tai, and Y. Kodama, DT Patent No. 2831568; Chem. Abstr., 90, 186980 (1979).

    Google Scholar 

  66. W. J. Wheeler, US Patent No. 4035361; Chem. Abstr., 87, 135371 (1977).

    Google Scholar 

  67. K. Kariyone, M. Kurita, H. Yasawa, and T. Oku, DT Patent No. 2262262; Chem. Abstr., 79, 92244 (1973).

    Google Scholar 

  68. L. Doub, J. S. Kalternborn, and D. Shweiss, US Patent No. 3595734; Chem. Abstr., 85, 108863 (1976).

    Google Scholar 

  69. L. Doub and J. S. Kalternborn, US Patent No. 3873523.; Chem. Abstr., 83; 58807 (1975).

    Google Scholar 

  70. A. E. Alburn and W. Dwonch, US Patent No. 3932321; Chem. Abstr., 85, 32998 (1976).

    Google Scholar 

  71. T. H. Cronin, US Patent No. 3847900; Chem. Abstr., 82, 57681 (1975).

    Google Scholar 

  72. C. Palomo and L. Antonio, DT Patent No. 2408171; Chem. Abstr., 81, 152210 (1974).

    Google Scholar 

  73. F. Lund and L. Tybring, Nature, New Biol., 236, 153 (1972).

    Google Scholar 

  74. F. Lund, DT Patent No. 2430375; Chem. Abstr., 83, 58850 (1975).

    Google Scholar 

  75. G. A. Veinberg, K. I. Dikovskaya, E. M. Belevich, S. A. Giller, and A. S. Khokhlov, USSR Inventor's Certificate No. 516691; Byull. Izobret., No. 21, 89 (1976).

  76. I. Busko-Oszczapowich and J. Cieslak, Acta Pol. Pharm., 30, 43 (1973).

    Google Scholar 

  77. I. Busko-Oszczapowich and J. Cieslak, GB Patent No. 1312030; Chem. Abstr., 79, 18700 (1973).

    Google Scholar 

  78. R. G. Micetich, C. G. Chin, and R. B. Morin, Tetrahedron Lett., No. 13, 967 (1976).

    Google Scholar 

  79. R. D. Carrol, D. K. Pirie, W. M. Welch, and E. S. Hamanaka, DT Patent No. 2253781; Chem. Abstr., 79, 42490 (1973).

    Google Scholar 

  80. R. Gericke, E. Poetsch, H. Juraszuk, J. Suebert, W. Strehlow, and R. Gottschlich, DT Patent No. 2626026; Chem. Abstr., 88, 105383 (1978).

    Google Scholar 

  81. V. Henri and V. Lunn, USSR Inventor's Certificate No, 686621; Byull. Izobret., No. 34, 244 (1979).

  82. H. W. O. Weissenburger and M. G. van der Hoeven, Rec. Trav. Chim., 89, 1081 (1970).

    Google Scholar 

  83. E. Visher, Helv. Chim. Acta, 51, 1108 (1968).

    Google Scholar 

  84. D. A. Johnson, S. P. Brundidge, A. L. Vulkano, C. Sapino Jr., H. Mahan, and J. G. Grossman, US Patent No. 3932392; Chem. Abstr., 85, 33039 (1976).

    Google Scholar 

  85. T. Ishimary and Y. Codama, DT Patent No. 2151530; Chem. Abstr., 77, 34544 (1972).

    Google Scholar 

  86. E. Bauershmidt, D. Bormann, and M. Worn, DT Patent No. 2243242; Chem. Abstr., 80, 114618 (1974).

    Google Scholar 

  87. K. Hattori, J. Ueda, K. Endo, D. Morino, A. Morimoto, K. Kauyone, M. Kurita, M. Hashimoto, and O. Nishiwaki, DT Patent No. 2332045; Chem. Abstr., 80, 95981 (1974).

    Google Scholar 

  88. N. Asako, T. Soma, and C. Harukawa, Jpn. Patent No. 7748991; Chem. Abstr., 89, 21547 (1978).

    Google Scholar 

  89. T. Ishimary and M. Kawabata, DT Patent No. 2523280; Chem. Abstr., 84, 135692 (1976).

    Google Scholar 

  90. P. Claes, A. Vlietinck, E. Roets, H. Vanderhaeghe, and S. Toppet, J. Chem. Soc., Perkin Trans. I, No. 9, 932 (1973).

    Google Scholar 

  91. A. Vlietinck, E. Roels, P. Claes, G. Jassen, and H. Vanderhaeghe, J. Chem. Soc., Perkin Trans. I, No. 9, 937 (1973).

    Google Scholar 

  92. R. E. Gutowski, US Patent No. 3719667; Chem. Abstr., 78, 147944 (1973).

    Google Scholar 

  93. R. B. Morin, B. G. Jackson, R. A. Mueller, E. R. Lavangino, W. B. Scanlon, and S. L. Andrews, J. Am. Chem. Soc., 91, 1401 (1969).

    Google Scholar 

  94. T. S. Chou, DT Patent No. 2323395; Chem. Abstr., 80, 48013 (1974).

    Google Scholar 

  95. T. S. Chou, Tetrahedron Lett., No. 9, 725 (1974).

    Google Scholar 

  96. J. J. de Coning, J. H. Kooreman, H. S. Tan, and J. Werweij, J. Org. Chem., 40, 1346 (1975).

    Google Scholar 

  97. Koninklijke Nederlandishe Gist-en Spiritus-Fabriek N. V., DT Patent No. 2107650; Chem. Abstr., 76, 3879 (1972).

    Google Scholar 

  98. J. Werweij, H. S. Tan, and J. H. Kooreman, DT Patent No. 2240224; Chem. Abstr., 83, 136314 (1973).

    Google Scholar 

  99. T. S. Chou, J. R. Burgtorf, A. L. Ellis, S. R. Lammert, and C. P. Kukolja, J. Am. Chem. Soc., 95, 1609 (1974).

    Google Scholar 

  100. H. Tanida and T. Tsuji, DT Patent No. 2333256; Chem. Abstr., 80, 95976 (1974).

    Google Scholar 

  101. J. Werweij and H. S. Tan, DT Patent No. 2406165; Chem. Abstr., 81, 152253 (1974).

    Google Scholar 

  102. J. Werweij and H. S. Tan, DT Patent No. 2505280; Chem. Abstr., 83, 193062 (1975).

    Google Scholar 

  103. R. Broggi and M. Falciani, DT Patent No. 2724286; Chem. Abstr., 88, 89696 (1978).

    Google Scholar 

  104. H. Ishimary, Jpn. Patent No. 79112891; Chem. Abstr., 92, 41435 (1980).

    Google Scholar 

  105. B. G. Christensen and L. D. Cama, US Patent No. 4071529; Chem. Abstr., 89, 6318 (1978).

    Google Scholar 

  106. T. R. Beattie, L. D. Cama, B. G. Christensen, and F. P. Dinnino, US Patent No. 4150156; Chem. Abstr., 91, 57041 (1979).

    Google Scholar 

  107. W. A. Slusarchuk, E. M. Gordon, and W. H. Koster, DT Patent No. 2754742; Chem. Abstr., 90, 103977 (1979).

    Google Scholar 

  108. F. E. Roberts, USSR Inventor's Certificate No. 608477; Byull. Izobret., No. 19, 172 (1978).

  109. K. Kuetlein and H. Jensen, DT Patent No. 2337443; Chem. Abstr., 82, 171002 (1975).

    Google Scholar 

  110. R. D. G. Cooper, G. V. Kaiser, C. F. Murphy, E. M. van Heyningen, and J. A. Webber, DT Patent No. 1940080; Chem. Abstr., 74, 22863 (1971).

    Google Scholar 

  111. E. Keisewetter and S. Herrling, DT Patent No. 2026508; Chem. Abstr., 76, 99650 (1972).

    Google Scholar 

  112. E. Keisewetter and S. Herrling, US Patent No. 3926954; Chem. Abstr., 85, 33042 (1976).

    Google Scholar 

  113. A. C. Adams, US Patent No. 3479338; Chem. Abstr., 72, 31783 (1970).

    Google Scholar 

  114. T. M. Vorozhkina, I. T. Strukov, and M. F. Shostakovskii, Zh. Obshch. Khim., 34, 1464 (1964).

    Google Scholar 

  115. G. A. Veinberg, É. P. Popova, A. M. Kats, and É. Ya. Lukevich, Khim.-farm. Zh., No. 10, 48 (1980).

    Google Scholar 

  116. G. Nannini, G. Molgora, G. Biasoli, P. Cozzi, F. Casabuona, G. Galli, D. Saverino, L. Sala, C. Confalonieri, P. N. Gicaldi, G. Vita, J. Decarneri, G. Meinardi, G. Monti, and A. Bianchi, Arzneim. — Forsc.-Drug Res., 27, 343 (1977).

    Google Scholar 

  117. P. Bamberg, B. A. Ekstrom, and B. O. H. Sjoberg, Acta Chem. Scand., 22, 367 (1968).

    Google Scholar 

  118. P. Bamberg, B. A. Ekstrom, and B. O. N. Sjoberg, FR Patent No. 1507866; Chem. Abstr., 70, 47434 (1969).

    Google Scholar 

  119. L. P. Puigdellivol, ES Patent No. 470902; Chem. Abstr., 91, 140851 (1979).

    Google Scholar 

  120. A. P. Da Luz, ZA Patent No. 7301720; Chem. Abstr., 83, 58805 (1975).

    Google Scholar 

  121. R. J. Stoodley, DT Patent No. 2202725; Chem. Abstr., 77, 126614 (1972).

    Google Scholar 

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 147–162, February, 1982.

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Veinberg, G.A., Petrulyanis, L.N. & Lukevits, É.Y. Silyl methods for the modification of penicillin and cephalosporin (review). Chem Heterocycl Compd 18, 111–123 (1982). https://doi.org/10.1007/BF00512950

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