Skip to main content
Log in

Synthesis of Ftorafur (review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Published data on methods for the synthesis of the antitumor compound “Ftorafur” by the tetrahydrofurylation of 5-fluorouracil and its derivatives and also by fluorination, cyclization, solvolysis, oxidation, and other reactions are reviewed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature Cited

  1. A. V. Stetsenko, Vest. Kievskogo Un-ta, 24, 42 (1983).

    Google Scholar 

  2. Daikin Industries Co., Japanese Patent No. 59681. Derwent CPI, 48676A/27.

  3. Daikin Industries Co., Japanese Patent No. 36281. Derwent CPI, 32507B/17.

  4. R. Duschinsky, E. Pleven, and C. Heidelberg, J. Am. Chem. Soc., 79, 4559 (1957).

    Google Scholar 

  5. R. A. Zhuk, History of the Creation of Ftorafur [in Russian]; S. A. Giller, Life and Scientific Activity [in Russian] (editor Ya. P. Stradyn'), Zinatne, Riga (1982), p. 103.

  6. Ya. P. Stradyn', Experimental and Clinical Pharmacotherapy [in Russian], Zinatne, Riga, No. 12, 5 (1983).

    Google Scholar 

  7. R. A. Zhuk, L. Kaulina, A. Ludzisa, E. Liepins, and M. Lidaks, Nucleic Acids Symp. Ser., 9, 123 (1981).

    Google Scholar 

  8. Ftorafur. An Antitumor Drug (Pamphlet), Zinatne, Riga (1979).

  9. Ftorafur. A New Soviet Antitumor Preparation [in Russian], Institut Organicheskogo Sinteza, Riga (1972).

  10. S. A. Giller, R. A. Zhuk, and M. Yu. Lidak, éksp. i Klin. Farmakoter., No. 7, 9 (1977).

    Google Scholar 

  11. R. A. Zhuk (ed.), Ftorafur. Proceedings of the International Symposium on Ftorafur, Riga, 1979, Zinatne, Riga (1985).

    Google Scholar 

  12. A. A. Zidermane, Fluoropyrimidines in the Chemotherapy of Tumors [in Russian], Zinatne, Riga (1982).

    Google Scholar 

  13. N. G. Blokhina, B. T. Garibdzhanyan, M. Yu. Lidak, and A. B. Syrkin, The Antitumor Product Ftorafur [in Russian] (1981) (cited in [12]).

    Google Scholar 

  14. A. Eisenstadt, R. R. G. Haber, and U. Michael, Israeli Patent No. 52565. Chem. Abs., 93, 168296 (1980).

    Google Scholar 

  15. S. Hashimoto and T. Suzue, J. Synth. Org. Chem. Japan, 38, 528 (1980).

    Google Scholar 

  16. J. Žemlička, R. Gassner, J. V. Fleisler, and J. P. Horwitz, J. Am. Chem. Soc., 94, 3213 (1972).

    Google Scholar 

  17. M. Yasumoto, A. Moriyama, N. Unemi, S. Hashimoto, and T. Suzue, J. Med. Chem., 20, 1592 (1977).

    Google Scholar 

  18. J. Yamashita, I. Yamawaki, S. Ueda, M. Yasumoto, N. Unemi, and S. Hashimoto, Chem. Pharm. Bull., 30, 4258 (1982).

    Google Scholar 

  19. H. Fujita, S. Hiller Memorial Lectures, Riga (1990).

  20. O. Miyashita, K. Matsumura, T. Kasahara, H. Shimadzu, and N. Hashimoto, Chem. Pharm. Bull., 30, 887 (1982).

    Google Scholar 

  21. S. Osaki, Y. Watanabe, T. Hoshiko, T. Nagasi, T. Ogasawara, H. Furukawa, A. Uemura, K. Ishikawa, H. Mori, A. Hoshi, M. Iigo, and R. Tokuzen, Chem. Pharm. Bull., 34, 150 (1986).

    Google Scholar 

  22. H. Nomura, Y. Yoshioka, and I. Minami, Chem. Pharm. Bull., 27, 899 (1979).

    Google Scholar 

  23. Netherlands Patent No. 7702516 (1977). Derwent CPI, 2436A/02. Y. Hoshide, Y. Hashimoto, H. Ogawa, and S. Tasaka, German Patent No. 2709839; Chem. Abs., 88, 121667 (1978).

    Google Scholar 

  24. Y. Hoshide, Y. Hashimoto, H. Ogawa, and S. Tasaka, Japanese Patent No. 119880; Chem. Abs., 90, 204125 (1979).

    Google Scholar 

  25. I. Minami, Y. Yoshioka, and H. Nomura, Belgian Patent No. 848662 (1977); German Patent No. 2653398 (1977); Chem. Abs., 87, 135384 (1977); Japanese Patent No. 89679 (1977); Japanese Patent No. 9778 (1978); Japanese Patent No. 16484 (1979); Derwent CPI, 36283 Y/21.

    Google Scholar 

  26. A. Takamizawa and K. Hirai, Chem. Pharm. Bull., 13, 681 (1965).

    Google Scholar 

  27. N. Nagasawa, J. Kumashiro, and T. Takenishi, J. Org. Chem., 31, 2685 (1966).

    Google Scholar 

  28. S. Giller, R. A. Zhuk, and M. Yu. Lidak, Dokl. Akad. Nauk SSSR, 332 (1967).

  29. Y. Kojima, A. Okabe, A. Okubo, H. Izuka, and Y. Jinno, Japanese Patent No. 118477 (1977); Chem. Abs., 88, 105718 (1978).

    Google Scholar 

  30. Y. Kojima, A. Okabe, A. Okubo, H. Izuka, and Y. Jinno, Japanese Patent No. 105483 (1978); Chem. Abs., 90, 23106 (1979).

    Google Scholar 

  31. Mitsui Toatsu Chem. Ind., Japanese Patent No. 15285 (1981); Chem. Abs., 95, 7322 (1981).

    Google Scholar 

  32. A. Kojima, Y. Kono, Y. Ike, T. Yokoyama, and M. Odate, Netherlands Patent No. 7614220; Japanese Patent No. 89678 (1977); Japanese Patent No. 89680 (1977); Japanese Patent No. 85180 (1977); Chem. Abs., 87, 202041 (1977); Japanese Patent No. 142079 (1977); Japanese Patent No. 125177 (1977); German Patent No. 2656604 (1977); Chem. Abs., 87, 135397 (1977); Derwent CPI, 49783Y/28.

    Google Scholar 

  33. A. Kojima, Y. Jinno, S. Ike, T. Yokoyama, and M. Odate, Japanese Patent No. 2478 (1978); Chem. Abs., 89, 24347 (1978).

    Google Scholar 

  34. A. Kojima, T. Yokoyama, M. Odate, Y. Ike, and Y. Kamino, Japanese Patent No. 108987 (1978); Chem. Abs., 90, 137855 (1979).

    Google Scholar 

  35. T. Nakamura, Y. Hoshimoto, Y. Hoshide, K. Suzuki, and Y. Yoshida, Netherlands Patent No. 7702515 (1977); German Patent No. 2709838 (1978); Chem. Abs., 88, 152656 (1978). Japanese Patent No. 2479 (1978); Japanese Patent No. 31673 (1978); Japanese Patent No. 121771 (1978); Derwent CPI, 4538A/03.

    Google Scholar 

  36. O. Maruyama, T. Sato, T. Kawashima, H. Suehiro, S. Ishida, Y. Yanase, and A. Aoki, Japanese Patent No. 21178 (1978); Chem. Abs., 89, 24350 (1978).

    Google Scholar 

  37. T. Nakamura, Y. Hoshide, Y. Hashimoto, K. Suzuki, and Y. Yoshida, Japanese Patent No. 70287 (1979); Chem. Abs., 91, 193334 (1979).

    Google Scholar 

  38. Y. Otsuka, Y. Fujimori, and H. Kondo, Japanese Patent No. 27584 (1979); Chem. Abs., 91, 5246 (1979).

    Google Scholar 

  39. ABIC, Japanese Patent No. 98979 (1978); Chem. Abs., 90, 72224 (1979).

    Google Scholar 

  40. é. Ya. Lukevits, M. A. Trushule, V. é. Udre, and é. é. Liepin'sh, Izv. Akad. Nauk Latv. SSR. Ser. Khim., No. 3, 317 (1982).

    Google Scholar 

  41. K. Sakurai, Japanese Patent No. 2484 (1978); Chem. Abs., 89, 129530 (1978).

    Google Scholar 

  42. K. Sakurai, Japanese Patent No. 5986 (1979); Chem. Abs., 90, 204136 (1979).

    Google Scholar 

  43. Mitsui Toatsu Chem. Inc., Japanese Patent No. 139079 (1977); Derwent CPI, 2747A/02.

  44. é. Ya. Lukevits, M. A. Trushule, D. é, Zarinya, L. M. Ignatovich, and é. é. Liepin'sh, Zh. Obshch. Khim., 51, 827 (1981).

    Google Scholar 

  45. H. Fukatsu, T. Miyano, I. Iwatsuki, and I. Matsumoto, Japanese Patent No. 98785 (1979); Chem. Abs., 92, 146795 (1980).

    Google Scholar 

  46. T. Nakamura, Y. Hoshide, Y. Hashimoto, and K. Suzuki, Japanese Patent No. 55581 (1979); Chem. Abs., 91, 175384 (1979).

    Google Scholar 

  47. K. Ishibashi, S. Ishiguro, and R. Komaki, German Patent No. 2834698 (1979); Chem. Abs., 91, 20334 (1979). Japanese Patent No. 46788 (1979); US Patent No. 4159378 (1979); Japanese Patent No. 84582 (1979); Derwent CPI, 24163B/13.

    Google Scholar 

  48. I. Minami, Y. Yoshioka, and H. Nomura, Belgian Patent No. 849651 (1977); Netherlands Patent No. 7614420 (1977); German Patent No. 2657709 (1977); Chem. Abs., 87, 135396 (1977); Japanese Patent No. 78887 (1977); Derwent CPI, 43509Y/25.

    Google Scholar 

  49. K. Sakai, Y. Inamoto, and H. Matsuzawa, Japanese Patent No. 46985 (1978); Chem. Abs., 89, 109567 (1978); Japanese Patent No. 20506 (1979); Derwent CPI, 41273A/23.

    Google Scholar 

  50. H. Fukatsu, T. Miyano, I. Iwatsuki, and I. Matsumoto, Japanese Patent No. 41882 (1979); Chem. Abs., 91, 123750 (1979).

    Google Scholar 

  51. H. Fukatsu, T. Miyano, I. Iwatsuki, and I. Matsumoto, Japanese Patent No. 103880 (1979); Chem. Abs., 92, 128954 (1980).

    Google Scholar 

  52. K. Ishibashi, S. Ishiguro, and R. Komaki, Japanese Patent No. 98784 (1979); Chem. Abs., 92, 146796 (1980).

    Google Scholar 

  53. Banya Pharm. Co., Japanese Patent No. 79290 (1979); Derwent CPI, 58592B/32.

  54. H. Fukatsu and T. Miyano, Japanese Patent No. 30187 (1979); Chem. Abs., 91, 39525 (1979).

    Google Scholar 

  55. H. Fukatsu and T. Miyano, Japanese Patent No. 52085 (1979); Chem. Abs., 91, 157760 (1979).

    Google Scholar 

  56. K. Sakurai, S. Aoyagi, H. Toyofuku, M. Ohki, T. Yoshizawa, and T. Kuroda, Chem. Pharm. Bull., 26, 3665 (1978).

    Google Scholar 

  57. K. Sakurai, Japanese Patent No. 27583 (1979); Chem. Abs., 91, 5245 (1979).

    Google Scholar 

  58. Y. Otsuka, Y. Fujimori, and H. Kondo, Japanese Patent No. 27585 (1979); Chem. Abs., 91, 5247 (1979).

    Google Scholar 

  59. T. Nakamura, Y. Hoshide, Y. Hashimoto, K. Suzuki, and H. Yoshida, Japanese Patent No. 52086 (1979); Chem. Abs., 91, 175381 (1979).

    Google Scholar 

  60. T. Umemoto, E. Ogura, T. Mukono, Japanese Patent No. 112073 (1986); Chem. Abs., 106, 18602 (1987).

    Google Scholar 

  61. J. Yamashita, M. Yasumoto, and S. Hashimoto, Chem. Pharm. Bull., 31, 3872 (1983).

    Google Scholar 

  62. T. Sato, T. Kawashima, H. Suehiro, O. Maruyama, and M. Yokoyama, Japanese Patent No. 27579 (1979); Chem. Abs., 91, 20539 (1979).

    Google Scholar 

  63. T. Narimoto and Y. Ichikawa, Japanese Patent No. 131587 (1977); Chem. Abs., 88, 105399 (1978).

    Google Scholar 

  64. T. Narimoto and Y. Ichikawa, Japanese Patent No. 131586 (1977); Chem. Abs., 88, 121230 (1978).

    Google Scholar 

  65. T. Ishida and K. Akashi, Japanese Patent No. 127981 (1974); Chem. Abs., 83, 10132 (1975).

    Google Scholar 

  66. N. Kamano, Japanese Patent No. 98976 (1978); Chem. Abs., 90, 54967 (1979).

    Google Scholar 

  67. S. Ozaki and K. Ishikawa, Japanese Patent No. 52182 (1976); Chem. Abs., 85, 192753 (1976).

    Google Scholar 

  68. Mitsui Toatsu Chem. Inc. Japanese Patent No. 33682 (1977); Derwent CPI 29784Y/17.

  69. K. Sakurai, M. Amino, and H. Toyofuku, Japanese Patent No. 77071 (1978); Chem. Abs., 89, 197590 (1978).

    Google Scholar 

  70. Institute of Organic Synthesis Academy of Sciences of the Latvian SSR, Russian Patent No. 791753 (1981); Derwent CPI 71150D/39.

  71. M. Yasumoto, J. Yamashita, I. Yamawaki, S. Ueda, S. Hashimoto, and T. Suzue, Japanese Patent No. 89481 (1978); Chem. Abs., 90, 54965 (1978).

    Google Scholar 

  72. N. Kamano, Japanese Patent No. 95980 (1978), Chem. Abs., 90, 23102 (1979); Japanese Patent No. 20508 (1979), Derwent CPI 69523A/39.

    Google Scholar 

  73. T. Hayasaka, K. Saito, and T. Goto, Japanese Patent No. 119881 (1978); Chem. Abs., 90, 204126 (1979).

    Google Scholar 

  74. O. Futsukaichi, S. Kumata, and H. Hayashiichi, Japanese Patent No. 137972 (1978); Chem. Abs., 90, 121647 (1979).

    Google Scholar 

  75. M. Yasumoto, S. Hashimoto, and T. Suzue, Japanese Patent No. 30188 (1979); Chem. Abs., 91, 39524 (1979).

    Google Scholar 

  76. M. H. Normant and M. M. Delepine, Compt. Rend., 228, 102 (1949).

    Google Scholar 

  77. E. L. Bliel, B. E. Nowak, R. A. Daignault, and V. G. Badding, J. Org. Chem., 30, 2441 (1956).

    Google Scholar 

  78. T. Kametani, Heterocycles, 6, 529 (1977).

    Google Scholar 

  79. T. Kametani, J. Heterocycl. Chem., 14, 473 (1977).

    Google Scholar 

  80. K. Kigasawa, M. Kukiki, K. Wakisaka, O. Kusama, H. Sugi, and K. Kawasaki, Japanese Patent No. 93778 (1977); Chem. Abs., 88, 121226 (1978).

    Google Scholar 

  81. Y. Kamano, Japanese Patent No. 84581 (1979); Chem. Abs., 91, 157764 (1979).

    Google Scholar 

  82. K. Kigasawa, M. Hiragi, K. Wakisaka, O. Kasuma, H. Sugi, and K. Kawasaki, Japanese Patent No. 118479 (1977); Chem. Abs., 88, 89707 (1978).

    Google Scholar 

  83. K. Mikami, A. Matsubara, Y. Ike, T. Nakano, and S. Ozaki, Japanese Patent No. 139076 (1977); Chem. Abs., 88, 105404 (1978).

    Google Scholar 

  84. A. Matsubara, K. Mikami, Y. Ike, T. Nakano, and S. Ozaki, Japanese Patent No. 139077 (1977); Chem. Abs., 88, 121231 (1978).

    Google Scholar 

  85. H. Fukatsu, T. Miyano, and I. Matsumoto, Japanese Patent No. 2480 (1978); Chem. Abs., 89, 59896 (1978).

    Google Scholar 

  86. K. Ishibashi, S. Ishiguro, and R. Komaki, Japanese Patent No. 46789 (1979); Chem. Abs., 91, 140863 (1979).

    Google Scholar 

  87. K. Kigasawa, M. Hiiragi, K. Wakisaka, O. Kusama, H. Sugi, K. Kawasaki, and T. Iwama, Japanese Patent No. 125178 (1978); Chem. Abs., 88, 170183 (1978).

    Google Scholar 

  88. Y. Minami, Y. Hirose, and N. Ida, Japanese Patent No. 118478 (1977); Chem. Abs., 88, 89706 (1978).

    Google Scholar 

  89. M. Yasumoto, T. Marunaka, S. Hashimoto, K. Harima, and T. Suzue, Japanese Patent No. 64281 (1975); Chem. Abs., 131631 (1975).

  90. J. Yamashita and M. Yasumoto, Nucleic Acids Symp. Ser., 10, 7 (1981).

    Google Scholar 

  91. M. Yasumoto, T. Marunaka, S. Hashimoto, K. Harima, and T. Suzue, Japanese Patent No. 285 (1977); Chem. Abs., 87, 68407 (1977).

    Google Scholar 

  92. H. Fukatsu, Japanese Patent No. 12875 (1978); Derwent CPI 20785A/11.

  93. K. Kigasawa, M. Hiiragi, K. Wakisaka, O. Kusuma, H. Sugi, and K. Kawasaki, Japanese Patent No. 7688 (1978); Chem. Abs., 88, 170185 (1978).

    Google Scholar 

  94. ABIC, Japanese Patent No. 34778 (1978); Chem. Abs., 89, 129531 (1978).

    Google Scholar 

  95. O. Asano, S. Makino, and B. Kato, Japanese Patent No. 59288 (1979); Chem. Abs., 91, 175386 (1979).

    Google Scholar 

  96. S. A. Giller, R. A. Zhuk, and M. Yu. Lidak, Russian Patent No. 272307 (1965); Byul. Izobr., No. 19, 28 (1970).

  97. S. A. Hiller, R. A. Zhuk, M. J. Lidaks, and A. A. Zidermane, British Patent No. 1168391 (1969); Chem. Abs., 72, 43715 (1970); French Patent No. 1574684 (1969); Chem. Abs., 73, 77281 (1970); US Patent No. 3635946 (1972); Chem. Abs., 76, 140864 (1972); Japanese Patent No. 4554 (1977); Chem. Abs., 88, 89985 (1978); Derwent CPI 32845F/00.

    Google Scholar 

  98. Ferrer International S. A., Spanish Patent No. 458679 (1978), Chem. Abs., 91, 20990 (1979).

    Google Scholar 

  99. K. Kigasawa, M. Hiiragi, K. Wakisaka, O. Kusuma, H. Sugi, K. Kawasaki, and S. Kimura, Japanese Patent No. 108987 (1977); Chem. Abs., 88, 190878 (1978).

    Google Scholar 

  100. K. Kigasawa, M. Hiiragi, K. Wakisaka, O. Kusuma, H. Sugi, K. Kawasaki, and S. Kimura, Japanese Patent No. 108988 (1977); Chem. Abs., 88, 136649 (1978).

    Google Scholar 

  101. é. Ya. Lukevits and L. M. Ignatovich, Izv. Akad. Nauk Latv. SSR. Ser. Khim., No. 4, 492 (1981).

    Google Scholar 

  102. T. Sowa, N. Suzuki, Y. Ono, T. Ishida, and K. Akashi, Japanese Patent No. 8282 (1976); Chem. Abs., 84, 180278 (1976).

    Google Scholar 

  103. N. Suzuki, S. Tagaki, K. Iizuka, M. Kobayashi, Y. Kobayashi, T. Sone, M. Wakabayashi, and T. Sowa, Japanese Patent No. 83476 (1977); Chem. Abs., 87, 202040 (1977).

    Google Scholar 

  104. K. Kigasawa, M. Hiiragi, K. Wakisaka, O. Kusuma, H. Sugi, and K. Kawasaki, Japanese Patent No. 142080 (1977); Chem. Abs., 88, 136661 (1978).

    Google Scholar 

  105. S. Ozaki, Japanese Patent No. 75079 (1976); Chem. Abs., 86, 106631 (1977).

    Google Scholar 

  106. S. Ozaki, Japanese Patent No. 111084 (1978); Derwent CPI 79176A/44.

  107. Y. Kojima, M. Odate, T. Yokoyama, Y. Ike, and Y. Jinno, Japanese Patent No. 68790 (1978); Chem. Abs., 89, 197591 (1978).

    Google Scholar 

  108. I. Nakajima, Y. Kanei, and T. Shinuchi, Japanese Patent No. 83385 (1977); Chem. Abs., 87, 184907 (1977).

    Google Scholar 

  109. I. Nakajima, Y. Kanei, and T. Shinuchi, Japanese Patent No. 83386 (1977); Chem. Abs., 87, 184908 (1977).

    Google Scholar 

  110. Y. Hoshide, Y. Hashimoto, H. Ogawa, and S. Tasaka, Japanese Patent No. 14981 (1979); Chem. Abs., 91, 57051 (1979).

    Google Scholar 

  111. S. Ozaki and T. Takahashi, Japanese Patent No. 5387 (1975); Chem. Abs., 82, 140297 (1975).

    Google Scholar 

  112. PCR Corp., US Patent No. 4024143 (1977); Japanese Patent No. 8836 (1981); Derwent CPI 37967Y/21.

  113. Mitsui Toatsu Chem. Inc., Japanese Patent No. 135988 (1978); Derwent CPI 2899B/02.

  114. S. A. Giller, M. Yu. Lidak, R. A. Zhuk, K. Ya. Pets, I. N. Getsova, and A. é. Berzinya, First All-Union Conference on the Chemotherapy of Malignant Tumors [in Russian], Riga (1968).

  115. R. A. Zhuk, Advances in the Chemistry of Furan [in Russian] é. Ya. Lukevits,(ed.), Zinatne, Riga (1978), p. 184.

    Google Scholar 

  116. S. A. Giller, M. Yu. Lidak, R. A. Zhuk, A. E. Berzinya, K. Ya. Pets, I. N. Getsova, and é I. Bruk, Khim. Geterotsikl. Soedin., No. 2, 375 (1969).

    Google Scholar 

  117. S. A. Giller, R. A. Zhuk, M. Yu. Lidak, A. E. Berzin', A. é. Getsova, K. Ya. Pets, and é. I. Bruk, Russian Patent No. 287952; Byul. Izobr., No. 47, 32 (1970).

  118. S. A. Giller, M. Yu. Lidak, R. A. Zhuk, K. Ya. Pets, I. N. Getsova, and A. E. Berzinya, Methods for Synthesis and Investigation of Antitumor Compounds [in Russian], No. Riga, 3, 109 (1970).

  119. Univ. of Utah, Belgian Patent No. 832067 (1975); Chem. Abs., 85, 160145 (1976).

    Google Scholar 

  120. L. B. Townsend, R. A. Earl, and S. J. Manning, German Patent No. 2519201 (1975); Chem. Abs., 84, 59575 (1976); US Patent No. 3960864; Canadian Patent No. 1024145 (1978); Chem. Abs., 88, 190889 (1978); Derwent CPI 78072W/47.

    Google Scholar 

  121. S. A. Hiller, A. A. Lazdinš, A. K. Vainberg, and A. B. Sidorov, Belgian Patent No. 830215; Chem. Abs., 85, 192757 (1976); German Patent No. 25190709 (1976); Japanese Patent No. 127087 (1976); Netherlands Patent No. 7504691 (1976); Chem. Abs., 86, 155685 (1977). British Patent No. 1462733 (1977); Chem. Abs., 87, 53361 (1977); US Patent No. 4039546 (1977); Chem. Abs., 87, 168342 (1977); French Patent No. 2313933 (1978); Swedish Patent No. 7504332 (1978); Swiss Patent No. 608013 (1978); Japanese Patent No. 12467 (1979); Derwent CPI 55X/01.

    Google Scholar 

  122. A. A. Lazdynysh, A. K. Veinberg, A. B. Sidorov, and S. A. Giller, Russian Patent No. 721439, Byul. Izobr., No. 10, 100 (1980).

  123. Y. Kobayashi, N. Suzuki, T. Sone, M. Wakabayashi, and T. Sowa, Japanese Patent No. 42887 (1977); Chem. Abs., 87, 135385 (1977).

    Google Scholar 

  124. Y. Kobayashi, K. Sako, Y. Hiyoshi, N. Suzuki, T. Sone, M. Wakabayashi, and T. Sowa, Japanese Patent No. 48676 (1977); Chem. Abs., 87, 201570 (1977).

    Google Scholar 

  125. Y. Kobayashi, S. Takagi, K. Nishimura, N. Suzuki, T. Sone, M. Wakabayashi, and T. Sowa, Japanese Patent No. 48677 (1977); Chem. Abs., 87, 201569 (1977).

    Google Scholar 

  126. Asahi Chem. Ind. Co., German Patent No. 2650918 (1977); Japanese Patent No. 59173 (1977); Japanese Patent No. 59174 (1977); Japanese Patent No. 59175 (1977); Derwent CPI 38416Y/22.

  127. T. Tomiyama, Japanese Patent No. 71480 (1977); Chem. Abs., 87, 184905 (1977).

    Google Scholar 

  128. H. Nakayama and M. Ishikura, Japanese Patent No. 108989 (1977); Chem. Abs., 88, 190877 (1978).

    Google Scholar 

  129. Y. Kojima, M. Odate, T. Yokoyama, Y. Ike, Y. Jinno, Japanese Patent No. 68791 (1978); Chem. Abs., 89, 180036 (1978).

    Google Scholar 

  130. Y. Fujimora and Y. Otsuka, Japanese Patent No. 127485 (1978); Chem. Abs., 90, 137853 (1979).

    Google Scholar 

  131. Y. Fujimori and Y. Otsuka, Japanese Patent No. 130677 (1978); Chem. Abs., 90, 152228 (1979).

    Google Scholar 

  132. Y. Fujimori and Y. Otsuka, Japanese Patent No. 130678 (1978); Chem. Abs., 90, 152227 (1979).

    Google Scholar 

  133. Y. Fujimori and Y. Otsuka, Japanese Patent No. 132580 (1978); Chem. Abs., 90, 121640 (1979).

    Google Scholar 

  134. Y. Kobayashi, S. Takagi, T. Sone, M. Wakabayashi, and R. Kodaira, Japanese Patent No. 135989 (1978); Chem. Abs., 90, 121642 (1979).

    Google Scholar 

  135. Mitsui Toatsu Chem. Ind., Japanese Patent No. 15284 (1981); Chem. Abs., 95, 7323 (1981).

    Google Scholar 

  136. K. Sakai and Y. Inamoto, Japanese Patent No. 31079 (1977); Chem. Abs., 87, 53375 (1977).

    Google Scholar 

  137. J. W. Shuppert and C. A. Angell, J. Chem. Phys., 67, 3050 (1977).

    Google Scholar 

  138. Y. Hoshide, Y. Hashimoto, H. Ogawa, S. Tasaka, and Y. Yoshide, Japanese Patent No. 48774 (1979); Chem. Abs., 91, 175680 (1979).

    Google Scholar 

  139. K. Kobayashi, T. Sone, N. Suzuki, M. Wakabayashi, and T. Sowa, Japanese Patent No. 36673 (1977); Chem. Abs., 87, 135387 (1977).

    Google Scholar 

  140. T. Merunaka, M. Yasumoto, S. Hashimoto, K. Harima, and T. Suzue, Japanese Patent No. 105673 (1975); Chem. Abs., 84, 59543 (1976).

    Google Scholar 

  141. T. Marunaka, M. Yasumoto, S. Hashimoto, K. Harima, and T. Suzue, Japanese Patent No. 105674 (1975); Chem. Abs., 84, 59542 (1976).

    Google Scholar 

  142. Y. Kobayashi, N. Suzuki, S. Takagi, K. Nishimura, Y. Hiyoshi, T. Sone, M. Wakabayashi, and T. Sowa, Japanese Patent No. 59172 (1977); Chem. Abs., 87, 168080 (1977).

    Google Scholar 

  143. Y. Fujimori, Japanese Patent No. 32488 (1979); Chem. Abs., 91, 107995 (1979).

    Google Scholar 

  144. T. Tomiyama, Japanese Patent No. 71479 (1977); Chem. Abs., 87, 202039 (1977).

    Google Scholar 

  145. N. Suzuki, T. Sone, K. Nishimura, E. Muramatsu, Y. Kobayashi, M. Wakabayashi, and T. Sowa, Japanese Patent No. 59171 (1977); Chem. Abs., 87, 135392 (1977); Japanese Patent No. 20505 (1979); Derwent CPI 45759Y/26.

    Google Scholar 

  146. Tanabe Pharm. Co., Japanese Patent No. 77054 (1978); Derwent CPI 57880A/32.

  147. N. Suzuki, K. Nazama, K. Iizuka, I. Himeno, Y. Kobayashi, T. Sone, M. Wakabayashi, and T. Sowa, Japanese Patent No. 83475 (1977); Chem. Abs., 87, 202038 (1977).

    Google Scholar 

  148. Michael Uri, Z. Sasson, and E. Schoenberger, Belgian Patent No. 859529 (1978); German Patent No. 2744956 (1978); Chem. Abs., 89, 24357 (1978); Japanese Patent No. 46987 (1978); German Patent No. 7903687 (1980); Derwent CPI 26970A/15.

    Google Scholar 

  149. S. A. Hiller, R. A. Zhuk, A. E. Berzina, L. A. Sherin, and A. A. Lazdinš, Belgian Patent No. 807556 (1974); German Patent No. 2357847 (1974); Chem. Abs., 81, 120680 (1974); French Patent No. 2207138 (1974); Chem. Abs., 82, 171019 (1975); Netherlands Patent No. 7315712 (1974); Chem. Abs., 83, 10138 (1975); US Patent No. 3912734 (1975); Chem. Abs., 84, 59538 (1976); British Patent No. 1438987 (1976); Chem. Abs., 86, 16696 (1977); Canadian Patent No. 999863 (1976); Swiss Patent No. 586696 (1977); Swedish Patent No. 7315630 (1980); Japanese Patent No. 39545 (1980); Chem. Abs., 94, 175151 (1981); Derwent CPI 41634V/23.

    Google Scholar 

  150. R. A. Zhuk, A. é. Berzinya, L. A. Sherin, L. T. Kaulinya, and S. A. Giller, Khim. Geterotsikl. Soedin., No. 9, 1258 (1977).

    Google Scholar 

  151. M. Yasumoto, T. Marunaka, S. Hashimoto, K. Harima, and T. Suzue, Japanese Patent No. 50383 (1975); Chem. Abs., 83, 206316 (1975).

    Google Scholar 

  152. M. Yasumoto, I. Yamayaki, T. Marunaka, and S. Hashimoto, J. Med. Chem., 21, 738 (1978).

    Google Scholar 

  153. M. Yasumoto, T. Marunaka, S. Hashimoto, K. Harima, and T. Suzue, Japanese Patent No. 50384 (1975); Chem. Abs., 83, 193366 (1975).

    Google Scholar 

  154. Ferrer International S. A., Spanish Patent No. 458887 (1978); Chem. Abs., 89, 197610 (1978).

    Google Scholar 

  155. T. Kanai and M. Ishino, Japanese Patent No. 65774 (1976); Chem. Abs., 86, 29862 (1977).

    Google Scholar 

  156. C. H. Lee, J. Y. Kim, W. J. Kim, and Y. H. Kim, Heterocycles, 31, 211 (1990).

    Google Scholar 

  157. M. Yasumoto, T. Marunaka, S. Hashimoto, K. Harima, and T. Suzue, Japanese Patent No. 146482 (1976); Chem. Abs., 87, 53355 (1977).

    Google Scholar 

  158. Y. Kobayashi, T. Sone, N. Suzuki, S. Furukawa, M. Wakabayashi, and R. Kodaira, Japanese Patent No. 144581 (1978); Chem. Abs., 90, 204127 (1979).

    Google Scholar 

  159. Y. Kobayashi, T. Sone, M. Wakabayashi, and R. Kodaira, Japanese Patent No. 149985 (1978); Chem. Abs., 91, 20991 (1979).

    Google Scholar 

  160. Y. Kobayashi, T. Sone, K. Sako, E. Muramatsu, I. Himeno, N. Suzuki, M. Wakabayashi, and T. Sowa, Japanese Patent No. 59179 (1977); Chem. Abs., 87, 184542 (1977).

    Google Scholar 

  161. T. Miyoshi, Japanese Patent No. 112884 (1978); Chem. Abs., 90, 87504 (1979).

    Google Scholar 

  162. H. Morizawa, T. Miyoshi, G. Yamazaki, K. Ajisaka, and M. Kaisho, Japanese Patent No. 39084 (1979); Chem. Abs., 91, 91660 (1979).

    Google Scholar 

  163. Y. Hoshide, Y. Hashimoto, H. Ogawa, K. Suzuki, and S. Tasaka, Japanese Patent No. 59289 (1979); Chem. Abs., 91, 175387 (1979).

    Google Scholar 

  164. M. Matsui and T. Ogawa, German Patent No. 2648239 (1977); Chem. Abs., 87, 102600 (1977); Japanese Patent No. 51373 (1977); Japanese Patent No. 51375 (1977); Japanese Patent No. 68189 (1977); Japanese Patent No. 68190 (1977); Japanese Patent No. 116483 (1977); Japanese Patent No. 37873 (1978); Japanese Patent No. 37874 (1978); Japanese Patent No. 12030 (1980); Chem. Abs., 93, 204684 (1980); Derwent CPI 31342Y/17.

    Google Scholar 

  165. T. Sone and N. Suzuki, Japanese Patent No. 108986 (1977); Chem. Abs., 88, 136647 (1978).

    Google Scholar 

  166. Y. Fujimori and Y. Otsuka, Japanese Patent No. 141283 (1978); Chem. Abs., 90, 121649 (1979).

    Google Scholar 

  167. N. Suzuki, G. Kimura, M. Tomari, and M. Yajima, Japanese Patent No. 83474 (1977); Chem. Abs., 87, 184906 (1977).

    Google Scholar 

  168. K. Ishibashi and R. Komaki, Japanese Patent No. 36280 (1979); Chem. Abs., 91, 107994 (1979).

    Google Scholar 

  169. Y. Kobayashi, S. Kiyohide, and M. Wakabayashi, Japanese Patent No. 5983 (1979); Chem. Abs., 91, 5244 (1976).

    Google Scholar 

  170. T. Sone and Y. Kobayashi, Japanese Patent No. 108985 (1977); Chem. Abs., 88, 170182 (1977).

    Google Scholar 

  171. K. Ishibashi, R. Komura, R. Komaki, and H. Yamai, Japanese Patent No. 137973 (1978); Chem. Abs., 90, 121646 (1979).

    Google Scholar 

  172. Institute of Physical Chemistry, Japanese Patent No. 59682 (1978); Japanese Patent No. 20510 (1979); Derwent CPI 48677A/27.

  173. Asahi Chem. Ind. Co., Japanese Patent No. 59169 (1977); Derwent CPI 45757Y/26.

  174. Y. Kobayashi, T. Sone, S. Takagi, K. Sako, and I. Himeno, Japanese Patent No. 108984 (1977); Chem. Abs., 88, 136648 (1978).

    Google Scholar 

  175. M. Miyoshi, K. Inoue, K. Matsumoto, T. Iwasaka, and H. Horikawa, Japanese Patent No. 5984 (1979); Chem. Abs., 90, 204135 (1979).

    Google Scholar 

  176. M. Miyoshi, Japanese Patent No. 79287 (1979); Derwent CPI 58589B/32.

  177. Tanabe Pharm. Co., Japanese Patent No. 79289 (1979); Derwent CPI 58591B/32.

  178. T. Iwasaki, T. Nishitani, H. Horikawa, and I. Inoue, Tetrahedron Lett., 22, 1029 (1981).

    Google Scholar 

  179. N. Suzuki, T. Sone, S. Takage, E. Muramatsu, Y. Kobayashi, M. Wakabayashi, and T. Sowa, Japanese Patent No. 59168 (1977); Chem. Abs., 87, 168079 (1977).

    Google Scholar 

  180. M. Miyoshi, K. Inoue, K. Matsumoto, and T. Iwasaki, Japanese Patent No. 79288 (1979); Chem. Abs., 92, 6551 (1980).

    Google Scholar 

  181. Hoffmann-La-Roche AG, Japanese Patent No. 144678 (1977).

  182. R. A. Earl and L. B. Townsend, J. Heterocycl. Chem., 9, 1141 (1972).

    Google Scholar 

  183. L. B. Townsend and R. A. Earl, US Patent Appl. 405532 (1973); Chem. Abs., 81, 63664 (1974).

    Google Scholar 

  184. Ferrer International S. A., Spanish Patent No. 458886 (1978); Chem. Abs., 89, 197596 (1978).

    Google Scholar 

  185. O. Miyashita, K. Matsumura, H. Shimadzu, and N. Hashimoto, Belgian Patent No. 853065 (1977); Japanese Patent No. 118480 (1977); Japanese Patent No. 71086 (1978); Chem. Abs., 89, 215427 (1978); Japanese Patent No. 124276 (1978); Derwent CPI 70715Y/40.

    Google Scholar 

  186. O. Miyashita, K. Matsumura, H. Shimadzu, and N. Hashimoto, Chem. Pharm. Bull., 29, 3181 (1981).

    Google Scholar 

  187. Takeda Chem. Ind. Co., Japanese Patent No. 102573 (1980); Derwent CPI 66722C/38.

  188. Y. Kojima and M. Odate, Japanese Patent No. 137974 (1978); Chem. Abs., 90, 121645 (1979); Japanese Patent No. 2716 (1982); Derwent CPI 3334B/02.

    Google Scholar 

  189. Y. Fujimori, Japanese Patent No. 59290 (1979); Chem. Abs., 91, 175388 (1979).

    Google Scholar 

  190. Y. Fujimori, Japanese Patent No. 66688 (1979); Chem. Abs., 91, 157762 (1979).

    Google Scholar 

  191. M. Yasumoto, J. Yamashita, S. Hashimoto, and T. Suzue, Japanese Patent No. 40781 (1978); Chem. Abs., 89, 109568 (1978).

    Google Scholar 

  192. M. Yasumoto, J. Yamashita, and S. Hashimoto, Japanese Patent No. 39082 (1979); Chem. Abs., 91, 91662 (1979).

    Google Scholar 

  193. ABIC, Japanese Patent No. 98980 (1978); Chem. Abs., 90, 72225 (1979).

    Google Scholar 

  194. A. Osamu and K. Fumiyoshi, Japanese Patent No. 124275 (1978); Chem. Abs., 90, 121644 (1979).

    Google Scholar 

  195. Taiho Pharm. Co., Japanese Patent No. 23986 (1978); Japanese Patent No. 33030 (1986); Derwent CPI 29321A/16.

  196. I. Minami, Y. Yoshioka, and H. Nomura, Japanese Patent No. 53671 (1978); Chem. Abs., 89, 197588 (1978).

    Google Scholar 

  197. Taiho Pharm. Co., Belgian Patent No. 847886 (1977); Derwent CPI 18206Y/11.

  198. S. Hashimoto, M. Yasumoto, T. Marunaka, N. Unemi, K. Kitazato, and S. Fujii, British Patent No. 1518391 (1978).

  199. Taiho Pharm. Co., Japanese Patent No. 23985 (1978); Derwent CPI 29320A/16.

  200. Taiho Pharm. Co., Japanese Patent No. 23987 (1978); Derwent CPI 29322A/16.

  201. Taiho Pharm Co., Japanese Patent No. 136687 (1976); Japanese Patent No. 49077 (1980); Derwent CPI 2864Y/02.

  202. Y. Hoshide, Y. Hashimoto, H. Ogawa, and N. Tasaka, Japanese Patent No. 39083 (1979); Chem. Abs., 91, 91661 (1979).

    Google Scholar 

  203. Y. Yoshioka and M. Nomura, Japanese Patent No. 108988 (1978), Chem. Abs., 90, 137856 (1979); Japanese Patent No. 20509 (1979); Derwent CPI 77593A/43.

    Google Scholar 

  204. S. Ozaki, H. Mizuno, K. Ishikawa, and H. Mori, Japanese Patent No. 33683 (1977); Chem. Abs., 87, 168350 (1977).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1590–1620, December, 1991.

The authors thank T. Shidlovskaya for assitance in the compilation of the tables.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Lukevits, É., Zablotskaya, A. Synthesis of Ftorafur (review). Chem Heterocycl Compd 27, 1271–1299 (1991). https://doi.org/10.1007/BF00515572

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00515572

Keywords

Navigation