Title:
BENZISOXAZOLE COMPOUND
Document Type and Number:
WIPO Patent Application WO/2007/126041
Kind Code:
A1
Abstract:
Disclosed is a compound represented by the general formula (I) or a salt thereof:
(I) wherein any one of R1, R2 and R3 represents a group represented by the formula:
-(CH2)m-NR11R12 (wherein m is 1 or 2; and R11 and R12 independently
represent a hydrogen atom or a C1-6 alkyl group or may, together with a nitrogen
atom to which R11 and R12 are bound, form a 4- or 5-membered cyclic group); the remaining
two of R1, R2 and R3 independently represent a group represented by the formula:
-(O)n-R21 (wherein n is 0 or 1; and R21 represents a hydrogen atom, a C1-6 alkyl
group, a C2-6 alkenyl group, a C2-6 alkynyl group, or the like); and R4 represents
a C1-6 alkyl group which may have a substituent or the like.
Inventors:
SASAKI ATSUSHI (JP)
UENO KOHSHI (JP)
SUZUKI YUICHI (JP)
HAMAOKA SHINICHI (JP)
SHIMMYO DAISUKE (JP)
TAKAHASHI YOSHINORI (JP)
KUROKAWA TOSHIKI (JP)
KAZUTA YUJI (JP)
OGURA HIROO (JP)
FUKUSHIMA TATSUTO (JP)
UENO KOHSHI (JP)
SUZUKI YUICHI (JP)
HAMAOKA SHINICHI (JP)
SHIMMYO DAISUKE (JP)
TAKAHASHI YOSHINORI (JP)
KUROKAWA TOSHIKI (JP)
KAZUTA YUJI (JP)
OGURA HIROO (JP)
FUKUSHIMA TATSUTO (JP)
Application Number:
PCT/JP2007/059146
Publication Date:
November 08, 2007
Filing Date:
April 27, 2007
Export Citation:
Assignee:
EISAI R&D MAN CO LTD (JP)
SASAKI ATSUSHI (JP)
UENO KOHSHI (JP)
SUZUKI YUICHI (JP)
HAMAOKA SHINICHI (JP)
SHIMMYO DAISUKE (JP)
TAKAHASHI YOSHINORI (JP)
KUROKAWA TOSHIKI (JP)
KAZUTA YUJI (JP)
OGURA HIROO (JP)
FUKUSHIMA TATSUTO (JP)
SASAKI ATSUSHI (JP)
UENO KOHSHI (JP)
SUZUKI YUICHI (JP)
HAMAOKA SHINICHI (JP)
SHIMMYO DAISUKE (JP)
TAKAHASHI YOSHINORI (JP)
KUROKAWA TOSHIKI (JP)
KAZUTA YUJI (JP)
OGURA HIROO (JP)
FUKUSHIMA TATSUTO (JP)
International Classes:
C07D413/06; A61K31/437; A61K31/454; A61K31/4545; A61K31/497; A61K31/501; A61K31/506; A61P1/14; A61P25/14; A61P25/16; A61P25/22; A61P25/24; A61P25/28; A61P43/00; C07D413/14; C07D471/04
Domestic Patent References:
| WO1992017475A1 | 1992-10-15 | |||
| WO1993004063A1 | 1993-03-04 |
Foreign References:
| JP2003063994A | 2003-03-05 | |||
| US5538984A | 1996-07-23 | |||
| EP0428437A1 | 1991-05-22 | |||
| JP2000219678A | 2000-08-08 |
Other References:
TONG W. ET AL., J. MED. CHEM., vol. 39, no. 2, 1996, pages 380 - 387, XP000567049
VILLALOBOS A., J. MED. CHEM., vol. 37, no. 17, 1994, pages 2721 - 2734, XP001073613
See also references of EP 2017275A4
LANCET, vol. 308, 1976, pages 1403
DRUGS, vol. 61, 2001, pages 41 - 52
AM. J. MED. GENET., vol. 116, 2003, pages 111 - 116
NEUROLOGY, vol. 63, 2004, pages 1579 - 1585
J. NEUROPATHOL. EXP. NEUROL., vol. 43, 1984, pages 359 - 368
J. NEUROSCI. RES., vol. 27, 1990, pages 576 - 586
T. W. GREENE; P. G. M. WUTS: "Protective Groups in Organic Chemistry", 1999, JOHN WILEY & SONS, INC., pages: 246 - 292
T. W. GREENE; P. G. M. WUTS: "Protective Groups in Organic Chemistry, Third Edition", 1999, JOHN WILEY & SONS, INC., pages: 17 - 245
VILLALOBOS, A. ET AL., J. MED. CHEM., vol. 38, no. 15, 1995, pages 2802
OLIVER, J. E.; WATERS, R. M.; LUSBY W. R., J. ORG. CHEM., vol. 54, no. 20, 1989, pages 4970
T. W. GREENE; P. G. M. WUTS: "Protective Groups in Organic Chemistry, Third Edition", 1999, JOHN WILEY & SONS, INC., pages: 246 - 292
SHEN, X.; VAN HEININGEN, A., CAN. J. CHEM., vol. 70, no. 6, 1992, pages 1754 - 1761
MASCI, B.; SACCHEO, S., TETRAHEDRON, vol. 49, no. 46, 1993, pages 10739 - 10748
ANELLI, P.-L. ET AL., J. CHEM. SOC., CHEM. COMMUN., 1995, pages 2541 - 2545
BRINGMANN, G.; SAEB, W.; RUEBENACKER, M., TETRAHEDRON, vol. 55, no. 2, 1999, pages 423 - 432
T. W. GREENE; P. G. M. WUTS: "Protective Groups in Organic Chemistry, Third Edition", 1999, JOHN WILEY & SONS, INC., pages: 494 - 653
MADRAS, B. K., MED. CHEM. RES., vol. 3, no. 4, 1993, pages 209
BAXTER, E. W.; REITZ, A. B., ORGANIC REACTIONS, vol. 59, 2002, pages 1
EMERSON, W. S., ORGANIC REACTIONS, vol. 4, 1948, pages 174
LANE, C. F., SYNTHESIS, vol. 135, 1975
CTOWELL, J. C.; PEDEGIMAS, S. J., SYNTHESIS, vol. 127, 1974
ABDEL-MAGID, A. F. ET AL., J. ORG. CHEM., vol. 61, 1996, pages 384
ALTAMURA, M.; PERROTTA, E., J. ORG. CHEM., vol. 58, no. 1, 1993, pages 272
GMEINER, P.; SOMMER, J., ARCH. PHARM., vol. 323, no. 12, 1990, pages 991
MELLONI, P. ET AL., J. MED. CHEM., vol. 22, 1979, pages 183
ANDERSON, W. K.; VEYSOGLU, T., SYNTHESIS, 1974, pages 665
JAROCH, S. ET AL., BIOORG. MED. CHEM. LETT., vol. 14, no. 3, 2004, pages 743
NUSSBAUMER, P. ET AL., TETRAHEDRON LETT., vol. 47, no. 26, 1991, pages 4591
T. W. GREENE; P. G. M. WUTS: "Protective Groups in Organic Chemistry, Third Edition", 1999, JOHN WILEY & SONS, INC.
NICHOLS, D. E. ET AL., J. MED. CHEM., vol. 34, no. 1, 1991, pages 276
SATO, H. ET AL., CHEM. PHARM. BULL., vol. 39, no. 7, 1991, pages 1760
NICHOLS, D. E. ET AL., J. MED. CHEM., vol. 34, no. 1, 1991, pages 276
THACH, L. N. ET AL., SYNTH. COMMUN., vol. 23, no. 10, 1993
SAWYER, J. S. ET AL., J. ORG. CHEM., vol. 63, no. 18, 1998, pages 6338
LAI, G.; ANDERSON, W. K., TETRAHEDRON LETT., vol. 34, no. 43, 1993, pages 6849
MASQUELIN, T.; HENGARTNER, U.; STREITH, J, SYNTHESIS, 1995, pages 780
BANFIELD, S. C.; ENGLAND, D. B.; KERR, M. A., ORG. LETT., vol. 3, no. 21, 2001, pages 3325
J. TSUJI: "Palladium Reagents and Catalysts", 1995, JOHN WILEY & SONS
SHUTO, S. ET AL., TETRAHEDRON. LETT., vol. 37, no. 5, 1996, pages 641
DI GIOVANNI, M. C. ET AL., TETRAHEDRON: ASYMMETRY, vol. 7, no. 8, 1996, pages 2277
STAUDINGER, H; MEYER, J., HELV. CHIM. ACTA, vol. 2, 1919, pages 635
LEE, S. ET AL., BULL. KOREAN CHEM. SOC., vol. 25, no. 7, 2004, pages 1003
ANKALA, S. V.; FENTEANY, G., TETRAHEDRON LETT, vol. 43, no. 27, 2002, pages 4729
SCHMITTLING, E. A.; SAWYER, J. S., TETRAHEDRON LETT, vol. 32, no. 49, 1991, pages 7207
"Organic Reactions", vol. 42, 1992, JOHN WILEY & SONS, INC., pages: 335 - 656
T. W. GREENE; P. G. M. WUTS: "Protective Groups in Organic Chemistry", 1999, JOHN WILEY & SONS, INC., pages: 494 - 653
KLUTCHKO, S. ET AL., SYNTH. COMMUN., vol. 23, no. 7, 1993, pages 971
SASAKI, N. A. ET AL., TETRAHEDRON LETT., vol. 35, no. 2, 1994, pages 241
BEGER, J. ET AL., J. PRAKT. CHEM/CHEM-ZTG., vol. 334, no. 3, 1992, pages 269
NUHRICH, A.; ET AL., EUR. J. MED. CHEM., vol. 29, no. 1, 1994, pages 75
GREEN, I. R. ET AL., SYNTH. COMMUN., vol. 26, no. 5, 1996, pages 867
SINGH, V.; SAMANTA, B., SYNTH. COMMUN., vol. 27, no. 24, 1997, pages 4235
JING, X. ET AL., SYNTH. COMMUN., vol. 31, no. 6, 2001, pages 861
TAKAHASHI, K.; SHIMIZU, S.; OGATA, M., HETEROCYCLES, vol. 23, no. 6, 1985, pages 1483
SHARMA, A. P. ET AL., J. MED. CHEM., vol. 33, no. 12, 1990, pages 3222
T. W. GREENE; P. G. M. WUTS: "Protective Groups in Organic Chemistry, Third Edition", 1999, JOHN WILEY & SONS, INC., pages: 276 - 278
KAGAWA, H. ET AL., CHEM. PHARM. BULL., vol. 53, no. 5, 2005, pages 547
TATSUTA, K. ET AL., CHEM. LETT., 2002, pages 262
GUO, W. ET AL., SYNTH. COMMUN., vol. 35, 2005, pages 145
SHARMA, A. P. ET AL., J.MED. CHEM., vol. 33, no. 12, 1990, pages 3222
BOX, V. G. S; YIANNIKOUROS, G. P.;, HETEROCYCLES, vol. 31, no. 7, 1990, pages 1261
SIMIG, G.; SCHLOSSER, M., ACTA. CHIM. HUNG., vol. 131, no. 2, 1994, pages 217
BOX, V. G. S.; YIANNIKOUROS, G. P., HETEROCYCLES, vol. 31, no. 7, 1990, pages 1261
PENDRAK, I.; CHAMBERS, P. A., J. ORG. CHEM., vol. 60, no. 10, 1995, pages 3249
ANDAPPAN, M. M. S. ET AL., J. ORG. CHEM., vol. 69, no. 16, 2004, pages 5212
KUMPATY, H. J. ET AL., SYNTHESIS, vol. 14, 2003, pages 2206
KUMPATY, H. J.; WILLIAMSON, J. S.; BHATTACHARYYA, S., SYNTH. COMMUN., vol. 33, no. 8, 2003, pages 1411
J. ORG. CHEM., vol. 67, 2002, pages 1669 - 1677
VILLALOBOS A., J. MED. CHEM., vol. 37, no. 17, 1994, pages 2721 - 2734, XP001073613
See also references of EP 2017275A4
LANCET, vol. 308, 1976, pages 1403
DRUGS, vol. 61, 2001, pages 41 - 52
AM. J. MED. GENET., vol. 116, 2003, pages 111 - 116
NEUROLOGY, vol. 63, 2004, pages 1579 - 1585
J. NEUROPATHOL. EXP. NEUROL., vol. 43, 1984, pages 359 - 368
J. NEUROSCI. RES., vol. 27, 1990, pages 576 - 586
T. W. GREENE; P. G. M. WUTS: "Protective Groups in Organic Chemistry", 1999, JOHN WILEY & SONS, INC., pages: 246 - 292
T. W. GREENE; P. G. M. WUTS: "Protective Groups in Organic Chemistry, Third Edition", 1999, JOHN WILEY & SONS, INC., pages: 17 - 245
VILLALOBOS, A. ET AL., J. MED. CHEM., vol. 38, no. 15, 1995, pages 2802
OLIVER, J. E.; WATERS, R. M.; LUSBY W. R., J. ORG. CHEM., vol. 54, no. 20, 1989, pages 4970
T. W. GREENE; P. G. M. WUTS: "Protective Groups in Organic Chemistry, Third Edition", 1999, JOHN WILEY & SONS, INC., pages: 246 - 292
SHEN, X.; VAN HEININGEN, A., CAN. J. CHEM., vol. 70, no. 6, 1992, pages 1754 - 1761
MASCI, B.; SACCHEO, S., TETRAHEDRON, vol. 49, no. 46, 1993, pages 10739 - 10748
ANELLI, P.-L. ET AL., J. CHEM. SOC., CHEM. COMMUN., 1995, pages 2541 - 2545
BRINGMANN, G.; SAEB, W.; RUEBENACKER, M., TETRAHEDRON, vol. 55, no. 2, 1999, pages 423 - 432
T. W. GREENE; P. G. M. WUTS: "Protective Groups in Organic Chemistry, Third Edition", 1999, JOHN WILEY & SONS, INC., pages: 494 - 653
MADRAS, B. K., MED. CHEM. RES., vol. 3, no. 4, 1993, pages 209
BAXTER, E. W.; REITZ, A. B., ORGANIC REACTIONS, vol. 59, 2002, pages 1
EMERSON, W. S., ORGANIC REACTIONS, vol. 4, 1948, pages 174
LANE, C. F., SYNTHESIS, vol. 135, 1975
CTOWELL, J. C.; PEDEGIMAS, S. J., SYNTHESIS, vol. 127, 1974
ABDEL-MAGID, A. F. ET AL., J. ORG. CHEM., vol. 61, 1996, pages 384
ALTAMURA, M.; PERROTTA, E., J. ORG. CHEM., vol. 58, no. 1, 1993, pages 272
GMEINER, P.; SOMMER, J., ARCH. PHARM., vol. 323, no. 12, 1990, pages 991
MELLONI, P. ET AL., J. MED. CHEM., vol. 22, 1979, pages 183
ANDERSON, W. K.; VEYSOGLU, T., SYNTHESIS, 1974, pages 665
JAROCH, S. ET AL., BIOORG. MED. CHEM. LETT., vol. 14, no. 3, 2004, pages 743
NUSSBAUMER, P. ET AL., TETRAHEDRON LETT., vol. 47, no. 26, 1991, pages 4591
T. W. GREENE; P. G. M. WUTS: "Protective Groups in Organic Chemistry, Third Edition", 1999, JOHN WILEY & SONS, INC.
NICHOLS, D. E. ET AL., J. MED. CHEM., vol. 34, no. 1, 1991, pages 276
SATO, H. ET AL., CHEM. PHARM. BULL., vol. 39, no. 7, 1991, pages 1760
NICHOLS, D. E. ET AL., J. MED. CHEM., vol. 34, no. 1, 1991, pages 276
THACH, L. N. ET AL., SYNTH. COMMUN., vol. 23, no. 10, 1993
SAWYER, J. S. ET AL., J. ORG. CHEM., vol. 63, no. 18, 1998, pages 6338
LAI, G.; ANDERSON, W. K., TETRAHEDRON LETT., vol. 34, no. 43, 1993, pages 6849
MASQUELIN, T.; HENGARTNER, U.; STREITH, J, SYNTHESIS, 1995, pages 780
BANFIELD, S. C.; ENGLAND, D. B.; KERR, M. A., ORG. LETT., vol. 3, no. 21, 2001, pages 3325
J. TSUJI: "Palladium Reagents and Catalysts", 1995, JOHN WILEY & SONS
SHUTO, S. ET AL., TETRAHEDRON. LETT., vol. 37, no. 5, 1996, pages 641
DI GIOVANNI, M. C. ET AL., TETRAHEDRON: ASYMMETRY, vol. 7, no. 8, 1996, pages 2277
STAUDINGER, H; MEYER, J., HELV. CHIM. ACTA, vol. 2, 1919, pages 635
LEE, S. ET AL., BULL. KOREAN CHEM. SOC., vol. 25, no. 7, 2004, pages 1003
ANKALA, S. V.; FENTEANY, G., TETRAHEDRON LETT, vol. 43, no. 27, 2002, pages 4729
SCHMITTLING, E. A.; SAWYER, J. S., TETRAHEDRON LETT, vol. 32, no. 49, 1991, pages 7207
"Organic Reactions", vol. 42, 1992, JOHN WILEY & SONS, INC., pages: 335 - 656
T. W. GREENE; P. G. M. WUTS: "Protective Groups in Organic Chemistry", 1999, JOHN WILEY & SONS, INC., pages: 494 - 653
KLUTCHKO, S. ET AL., SYNTH. COMMUN., vol. 23, no. 7, 1993, pages 971
SASAKI, N. A. ET AL., TETRAHEDRON LETT., vol. 35, no. 2, 1994, pages 241
BEGER, J. ET AL., J. PRAKT. CHEM/CHEM-ZTG., vol. 334, no. 3, 1992, pages 269
NUHRICH, A.; ET AL., EUR. J. MED. CHEM., vol. 29, no. 1, 1994, pages 75
GREEN, I. R. ET AL., SYNTH. COMMUN., vol. 26, no. 5, 1996, pages 867
SINGH, V.; SAMANTA, B., SYNTH. COMMUN., vol. 27, no. 24, 1997, pages 4235
JING, X. ET AL., SYNTH. COMMUN., vol. 31, no. 6, 2001, pages 861
TAKAHASHI, K.; SHIMIZU, S.; OGATA, M., HETEROCYCLES, vol. 23, no. 6, 1985, pages 1483
SHARMA, A. P. ET AL., J. MED. CHEM., vol. 33, no. 12, 1990, pages 3222
T. W. GREENE; P. G. M. WUTS: "Protective Groups in Organic Chemistry, Third Edition", 1999, JOHN WILEY & SONS, INC., pages: 276 - 278
KAGAWA, H. ET AL., CHEM. PHARM. BULL., vol. 53, no. 5, 2005, pages 547
TATSUTA, K. ET AL., CHEM. LETT., 2002, pages 262
GUO, W. ET AL., SYNTH. COMMUN., vol. 35, 2005, pages 145
SHARMA, A. P. ET AL., J.MED. CHEM., vol. 33, no. 12, 1990, pages 3222
BOX, V. G. S; YIANNIKOUROS, G. P.;, HETEROCYCLES, vol. 31, no. 7, 1990, pages 1261
SIMIG, G.; SCHLOSSER, M., ACTA. CHIM. HUNG., vol. 131, no. 2, 1994, pages 217
BOX, V. G. S.; YIANNIKOUROS, G. P., HETEROCYCLES, vol. 31, no. 7, 1990, pages 1261
PENDRAK, I.; CHAMBERS, P. A., J. ORG. CHEM., vol. 60, no. 10, 1995, pages 3249
ANDAPPAN, M. M. S. ET AL., J. ORG. CHEM., vol. 69, no. 16, 2004, pages 5212
KUMPATY, H. J. ET AL., SYNTHESIS, vol. 14, 2003, pages 2206
KUMPATY, H. J.; WILLIAMSON, J. S.; BHATTACHARYYA, S., SYNTH. COMMUN., vol. 33, no. 8, 2003, pages 1411
J. ORG. CHEM., vol. 67, 2002, pages 1669 - 1677
Attorney, Agent or Firm:
ASAMURA, Kiyoshi et al. (New Ohtemachi Bldg.2-1, Ohtemachi 2-chome,Chiyoda-k, Tokyo 04, JP)
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