Design and synthesis of new prostaglandin D 2 receptor antagonists

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 18, 2011, Pages 5361-5371

  Iwahashi, Maki ^a   Takahashi, Eiji ^a   Tanaka, Motoyuki ^a   Matsunaga, Yoko ^a   Okada, Yutaka ^a   Matsumoto, Ryoji ^a   Nambu, Fumio ^a   Nakai, Hisao ^a   Toda, Masaaki ^a  

^a ONO PHARMACEUTICAL CO   (Japan)

Author keywords

Antagonist; DP receptor; Phenylacetic acid; Prostaglandin

Indexed keywords

(3 FLUORO 5 NITROPHENYL)ACETIC ACID; (3 METHYL 5 NITROPHENYL)ACETIC ACID; (3 METHYL 5 NITROPHENYL)ACETONITRILE; [(3 FLUORO 5 NITROPHENYL)ETHYNYL](TRIMETHYL)SILANE; [2 FLUORO 5 [[2 METHYL 4 [(4 METHYL 3,4 DIHYDRO 2H 1,4 BENZOXAZIN 2 YL)METHOXY]BENZOYL]AMINO]PHENYL]ACETIC ACID; [2 METHOXY 5 [[2 METHYL 4 [(4 METHYL 3,4 DIHYDRO 2H 1,4 BENZOXAZIN 2 YL)METHOXY]BENZOYL]AMINO]PHENYL]ACETIC ACID; [2 METHYL 3 [[2 METHYL 4 [(4 METHYL 3,4 DIHYDRO 2H 1,4 BENZOXAZIN 2 YL)METHOXY]BENZOYL]AMINO]PHENYL]ACETIC ACID; [2 METHYL 5 [[2 METHYL 4 [(4 METHYL 3,4 DIHYDRO 2H 1,4 BENZOXAZIN 2 YL)METHOXY]BENZOYL]AMINO]PHENYL]ACETIC ACID; [3 [[2 CHLORO 4 [(4 METHYL 3,4 DIHYDRO 2H 1,4 BENZOXAZIN 2 YL)METHOXY]BENZOYL]AMINO]PHENYL]ACETIC ACID; [3 [[2 METHYL 4 [(4 METHYL 3,4 DIHYDRO 2H 1,4 BENZOXAZIN 2 YL)METHOXY]BENZOYL]AMINO]PHENYL]ACETIC ACID; [3 [[4 [(4 METHYL 3,4 DIHYDRO 2H 1,4 BENZOXAZIN 2 YL)METHOXY]BENZOYL]AMINO]PHENYL]ACETIC ACID; [3 [ETHYL[4 [(4 METHYL 3,4 DIHYDRO 2H 1,4 BENZOXAZIN 2 YL)METHOXY]BENZOYL]AMINO]PHENYL]ACETIC ACID; [3 [METHYL[4 [(4 METHYL 3,4 DIHYDRO 2H 1,4 BENZOXAZIN 2 YL)METHOXY]BENZOYL]AMINO]PHENYL]ACETIC ACID; [3 FLUORO 5 [[2 METHYL 4 [(4 METHYL 3,4 DIHYDRO 2H 1,4 BENZOXAZIN 2 YL)METHOXY]BENZOYL]AMINO]PHENYL]ACETIC ACID; [3 METHYL 5 [[2 METHYL 4 [(4 METHYL 3,4 DIHYDRO 2H 1,4 BENZOXAZIN 2 YL)METHOXY]BENZOYL]AMINO]PHENYL]ACETIC ACID; [4 CHLORO 3 [[2 METHYL 4 [(4 METHYL 3,4 DIHYDRO 2H 1,4 BENZOXAZIN 2 YL)METHOXY]BENZOYL]AMINO]PHENYL]ACETIC ACID; [4 FLUORO 3 [[2 METHYL 4 [(4 METHYL 3,4 DIHYDRO 2H 1,4 BENZOXAZIN 2 YL)METHOXY]BENZOYL]AMINO]PHENYL]ACETIC ACID; [4 METHYL 3 [[2 METHYL 4 [(4 METHYL 3,4 DIHYDRO 2H 1,4 BENZOXAZIN 2 YL)METHOXY]BENZOYL]AMINO]PHENYL]ACETIC ACID; METHYL (3 AMINO 2 METHYLPHENYL)ACETATE; METHYL (3 AMINO 4 FLUOROPHENYL)ACETATE; METHYL (3 AMINO 4 METHYLPHENYL)ACETATE; METHYL (3 AMINO 5 FLUOROPHENYL)ACETATE; METHYL (3 AMINO 5 METHYLPHENYL)ACETATE; METHYL (3 FLUORO 5 NITROPHENYL)ACETATE; METHYL (3 METHYL 5 NITROPHENYL)ACETATE; METHYL (5 AMINO 2 FLUOROPHENYL)ACETATE; METHYL [3 (ETHYLAMINO)PHENYL]ACETATE; PROSTAGLANDIN D2; PROSTAGLANDIN RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ALKYLATION; ANIMAL CELL; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; COST EFFECTIVENESS ANALYSIS; DRUG DESIGN; DRUG POTENCY; DRUG PROTEIN BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROBORATION; HYDROGENATION; HYDROLYSIS; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANIMALS; BENZAMIDES; BINDING, COMPETITIVE; CHO CELLS; CRICETINAE; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; MALE; MOLECULAR CONFORMATION; PHENYLACETATES; RATS; RECEPTORS, IMMUNOLOGIC; RECEPTORS, PROSTAGLANDIN; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TISSUE DISTRIBUTION;

RATTUS;

EID: 80052588151     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.08.007     Document Type: Article

References (22)

1. R.A. Coleman Prostanoids Receptors D. Girdlestne, The IUPHAR Compendium of Receptor Characterization and Classification 1998 Burlington Press Cambridge 229 244
2. R.A. Coleman, W.L. Smith, and S. Narumiya Pharmacol. Rev. 46 1994 205
3. R.A. Lewis, N.A. Soter, P.T. Diamond, K.F. Austen, J.A. Oates, and L.J. Roverts II J. Immunol. 129 1982 1627
4. T. Matsuoka, M. Hirata, H. Tanaka, Y. Takahashi, T. Murata, K. Kabashima, Y. Sugimoto, T. Kobayashi, F. Ushikubi, Y. Aze, N. Yoshida, Y. Honda, H. Nagai, and S. Narumiya Science 287 2000 2013
5. W.J. Doyle, S. Boehm, and D.P. Skoner J. Allergy Clin. Immunol. 86 1990 924
6. S.L. Johnston, S. Smith, J. Harrison, W. Ritter, and P.H. Hawarth J. Allergy Clin. Immunol. 91 1993 903
7. K. Alving, R. Matran, and J.M. Lundberg Acta Physiol. Scand. 143 1991 93
8. D.F. Woodward, S.B. Hawley, L.S. Williams, T.R. Ralston, C.E. Protzman, C.S. Spada, and A.L. Nieves Invest. Ophthalmol. Vis. Sci. 31 1990 138
9. D.F. Woodward, A.L. Nieves, and J. Friedlaender Pharmacol. Exp. Ther. 279 1996 137
10. N.A. Soter, R.A. Lewis, E.J. Corey, and K.F. Austen J. Invest. Dermatol. 80 1983 115
11. R.J. Flower, E.A. Harvey, and W.P. Kingston Br. J. Pharmacol. 56 1976 229
12. K. Torisu, K. Kobayashi, M. Iwahashi, H. Egashira, Y. Nakai, Y. Okada, F. Nanbu, S. Ohuchida, H. Nakai, and M. Toda Bioorg. Med. Chem. Lett. 14 2004 4557
13. K. Torisu, K. Kobayashi, M. Iwahashi, Y. Nakai, T. Onoda, T. Nagase, I. Sugimoto, Y. Okada, R. Matsumoto, F. Nanbu, S. Ohuchida, H. Nakai, and M. Toda Bioorg. Med. Chem. Lett. 14 2004 4891
14. K. Torisu, K. Kobayashi, M. Iwahashi, Y. Nakai, T. Onoda, T. Nagase, I. Sugimoto, Y. Okada, R. Matsumoto, F. Nanbu, S. Ohuchida, H. Nakai, and M. Toda Bioorg. Med. Chem. 12 2004 4685
15. K. Torisu, K. Kobayashi, M. Iwahashi, Y. Nakai, T. Onoda, T. Nagase, I. Sugimoto, Y. Okada, R. Matsumoto, F. Nanbu, S. Ohuchida, H. Nakai, and M. Toda Bioorg. Med. Chem. 12 2004 5361
16. M. Iwahashi, A. Shimabukuro, T. Onoda, Y. Matsunaga, Y. Okada, R. Matsumoto, F. Nambu, H. Nakai, and M. Toda Bioorg. Med. Chem. 19 2011 4574
17. Iwahashi, M.; Kobayashi, K.; Nambu, F. WO03078409, 2003.
18. H. Kagechika, T. Himi, E. Kawachi, and K. Shudo J. Med. Chem. 32 1989 2292
19. A. Itai, Y. Toriumi, N. Tomioka, H. Kagechika, I. Azumaya, and K. Shudo Tetrahedron Lett. 30 1989 6177
20. Y. Toriumi, A. Kasuya, and A. Itai J. Org. Chem. 55 1990 259
21. K. Yamaguchi, G. Matsumura, H. Kagechika, I. Azumaya, Y. Ito, A. Itai, and K. Shudo J. Am. Chem. Soc. 113 1991 5474
22. A. Itai, Y. Toriumi, S. Saito, H. Kagechika, and K. Shudo J. Am. Chem. Soc. 114 1992 10649