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Part III: Nakamura K., Tsuji K., Konishi N., Matsuo M., Chem. Pharm. Bull., 41, 2050-2052 (1993).
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Chem. Pharm. Bull.
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Nakamura, K.1
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a) Ivey K. J., Am. J. Med., 75 (5A), 53-64 (1983);
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Ivey, K.J.1
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b) Nanra R. S., ibid., 75 (5A), 70-81 (1983);
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Nanra, R.S.1
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c) Allison M. C., Howatson A. G., Torrance C. J., Lee F. D., Russell R. I., N. Eng. J. Med., 327, 749-754 (1992).
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Allison, M.C.1
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Lee, F.D.4
Russell, R.I.5
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8
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0029179309
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ed. by Samuelsson B. et al., Raven Press, Ltd., New York
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b) Isakson P., Seibert K., Masferrer J., Salvemini D., Lee L., Needleman P., "Advances in Prostaglandin. Thromboxane, and Leukotriene Research," Vol. 23, ed. by Samuelsson B. et al., Raven Press, Ltd., New York, 1995, pp. 49-54.
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Isakson, P.1
Seibert, K.2
Masferrer, J.3
Salvemini, D.4
Lee, L.5
Needleman, P.6
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9
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0026761625
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a) Tsuji K., Nakamura K., Konishi N., Okumura H., Matsuo M., Chem. Pharm. Bull., 40, 2399-2409 (1992);
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Chem. Pharm. Bull.
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Tsuji, K.1
Nakamura, K.2
Konishi, N.3
Okumura, H.4
Matsuo, M.5
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10
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0027282120
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b) Nakamura K., Tsuji K., Konishi N., Okumura H., Matsuo M., ibid., 41, 894-906 (1993).
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Chem. Pharm. Bull.
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Nakamura, K.1
Tsuji, K.2
Konishi, N.3
Okumura, H.4
Matsuo, M.5
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11
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0343451805
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a) Gans K. R., Balles E. A., Galbraith W., Haber S. B., Kerr J. S., Newton R. C., Schmidt W. K., Smith C., Hewes W. E., Ackerman N. R., Pharmacologist, 29, 138 (1987);
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Pharmacologist
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Gans, K.R.1
Balles, E.A.2
Galbraith, W.3
Haber, S.B.4
Kerr, J.S.5
Newton, R.C.6
Schmidt, W.K.7
Smith, C.8
Hewes, W.E.9
Ackerman, N.R.10
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12
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0025160887
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b) Gans K. R., Galbraith W., Roman R. J., Haber S. B., Kerr J. S., Schmidt W. K., Smith C., Hewes W. E., Ackerman N. R., J. Pharmacol. Exp. Ther., 254, 180-187 (1990).
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Gans, K.R.1
Galbraith, W.2
Roman, R.J.3
Haber, S.B.4
Kerr, J.S.5
Schmidt, W.K.6
Smith, C.7
Hewes, W.E.8
Ackerman, N.R.9
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13
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0343451806
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note
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Compound 1 was metabolized to a 5-(methylsulfonyl)thiophene derivative in rats. Compound 1 also showed mutagenicity in a chromosome aberration test conducted by Toxicology Research Laboratories, Fujisawa Pharmaceutical Co., Ltd. (unpublished results).
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14
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0342581930
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note
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The energy levels and the orbital distributions of HOMO and LUMO, and the torsion angles of the benzene rings of the most stable conformer of 5-bromo-3-(4-acetylphenyl)-2-(4-fluorophenyl)thiophene (38) and that of 3-bromo-5-(4-acetylphenyl)-1-(4-fluorophenyl)pyrazole (39) were calculated by the MNDO method: e.g., the torsion angle of the 4-acetylphenyl ring was +77.7° (38) and +79.1° (39) and that of the 4-fluorophenyl ring was +77.4° (38) and +77.3° (39), respectively.
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15
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4344715685
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Eur. Patent 178035 (1986)
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Appleton R. A., Burford S. C., Hardern D. N., Wilkinson D., Eur. Patent 178035 (1986) [Chem. Abstr., 105, 42796f (1986)].
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Chem. Abstr.
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Appleton, R.A.1
Burford, S.C.2
Hardern, D.N.3
Wilkinson, D.4
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16
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0343451803
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note
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The production of the by-product 15 was suppressed when the reaction was conducted in AcOH.
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17
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0008054345
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Eur. Patent 418845 (1991)
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Matsuo M., Tsuji K., Konishi N., Nakamura K., Eur. Patent 418845 (1991) [Chem. Abstr., 115, 71593z (1991)].
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Chem. Abstr.
, vol.115
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Matsuo, M.1
Tsuji, K.2
Konishi, N.3
Nakamura, K.4
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19
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0343004498
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Eur. Patent 87629 (1983)
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a) Haber S. B., Eur. Patent 87629 (1983) [Chem. Abstr., 100, 22571x (1984)];
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Chem. Abstr.
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Haber, S.B.1
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20
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26144468297
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U.S. Patent 4302461 (1981)
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b) Cherkofsky S. C., U.S. Patent 4302461 (1981) [Chem. Abstr., 96, 104081a (1982)].
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Chem. Abstr.
, vol.96
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Cherkofsky, S.C.1
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21
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0343016173
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Manuscript in preparation
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Manuscript in preparation.
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22
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0028889567
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COX-2 inhibitors having a sulfonamide group were recently reported: a) Li J. J., Anderson G. D., Burton E. G., Cogburn J. N., Collins J. T., Garland D. J., Gregory S. A., Huang H.-C., Isakson P. C., Koboldt C. M., Logusch E. W., Norton M. B., Perkins W. E., Reinhard E. J., Seibert K., Veenhuizen A. W., Zhang Y., Reitz D. B., J. Med. Chem., 38, 4570-4578 (1995); b) Leblanc Y., Gauthier J. Y., Ethier D., Guay J., Mancini J., Riendeau D., Tagari P., Vickers P., Wong E., Prasit P., Bioorg. Med. Chem. Lett., 5, 2123-2128 (1995).
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J. Med. Chem.
, vol.38
, pp. 4570-4578
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Li, J.J.1
Anderson, G.D.2
Burton, E.G.3
Cogburn, J.N.4
Collins, J.T.5
Garland, D.J.6
Gregory, S.A.7
Huang, H.-C.8
Isakson, P.C.9
Koboldt, C.M.10
Logusch, E.W.11
Norton, M.B.12
Perkins, W.E.13
Reinhard, E.J.14
Seibert, K.15
Veenhuizen, A.W.16
Zhang, Y.17
Reitz, D.B.18
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23
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0029151693
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COX-2 inhibitors having a sulfonamide group were recently reported: a) Li J. J., Anderson G. D., Burton E. G., Cogburn J. N., Collins J. T., Garland D. J., Gregory S. A., Huang H.-C., Isakson P. C., Koboldt C. M., Logusch E. W., Norton M. B., Perkins W. E., Reinhard E. J., Seibert K., Veenhuizen A. W., Zhang Y., Reitz D. B., J. Med. Chem., 38, 4570-4578 (1995); b) Leblanc Y., Gauthier J. Y., Ethier D., Guay J., Mancini J., Riendeau D., Tagari P., Vickers P., Wong E., Prasit P., Bioorg. Med. Chem. Lett., 5, 2123-2128 (1995).
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Bioorg. Med. Chem. Lett.
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, pp. 2123-2128
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Leblanc, Y.1
Gauthier, J.Y.2
Ethier, D.3
Guay, J.4
Mancini, J.5
Riendeau, D.6
Tagari, P.7
Vickers, P.8
Wong, E.9
Prasit, P.10
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24
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0343451797
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note
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COX-1 inhibition at 100 μM: 0% (33), 8% (37); COX-2 inhibition at 100 μM: 19% (33), 49% (37).
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25
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0343016168
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note
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This product was used for the next step in the synthesis without further purification.
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26
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0021878424
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Tomisawa K., Kameo K., Matsunaga T., Saito S., Hosoda K., Asami Y., Sota K., Chem. Pharm. Bull., 33, 2386-2394 (1985).
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Chem. Pharm. Bull.
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Tomisawa, K.1
Kameo, K.2
Matsunaga, T.3
Saito, S.4
Hosoda, K.5
Asami, Y.6
Sota, K.7
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27
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0008155879
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Eur. Patent 554829 (1993)
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Matsuo M., Tsuji K., Ogino T., Konishi N., Eur. Patent 554829 (1993) [Chem. Abstr., 120, 8589r (1994)].
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(1994)
Chem. Abstr.
, vol.120
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Matsuo, M.1
Tsuji, K.2
Ogino, T.3
Konishi, N.4
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28
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0343887611
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note
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Supplied by Exploratory Research Laboratories, Fujisawa Pharmaceutical Co., Ltd. (Tsukuba, Ibaraki).
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