Melanin-concentrating hormone receptor 1 antagonists: Synthesis, structure-activity relationship, docking studies, and biological evaluation of 2,3,4,5-tetrahydro-1H-3-benzazepine derivatives

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 21, 2011, Pages 6261-6273

  Kasai, Shizuo ^a   Kamaura, Masahiro ^a   Kamata, Makoto ^a   Aso, Kazuyoshi ^a   Ogino, Hitomi ^a   Nakano, Yoshihide ^a   Watanabe, Kaoru ^a   Kaisho, Tomoko ^a   Tawada, Michiko ^a   Nagisa, Yasutaka ^a   Takekawa, Shiro ^a   Kato, Koki ^a   Suzuki, Nobuhiro ^a   Ishihara, Yuji ^a  

^a TAKEDA PHARMACEUTICAL COMPANY LIMITED   (Japan)

Author keywords

homology model; MCH; MCHR1 antagonist; obesity

Indexed keywords

1 (2 ACETYL 2,3,4,5, TETRAHYDRO 1H 2 BENZAZEPIN 8 YL) 4 CHLOROBUTAN 1 ONE; 1 (2 ACETYL 2,3,4,5, TETRAHYDRO 1H 2 BENZAZEPIN 8 YL) 4 [4 (4 CHLOROPHENYL)PIPERIDIN 1 YL] BUTAN 1 ONE; 1 (2 ACETYL 2,3,4,5, TETRAHYDROISOQUINOLIN 7 YL) 4 CHLOROBUTAN 1 ONE; 1 (3 ACETYL 2,3,4,5 TETRAHYDRO 1H 3 BENZAZEPIN 7 YL) 4 CHLOROBUTAN 1 ONE; 1 (3 ACETYL 2,3,4,5 TETRAHYDRO 1H 3 BENZAZEPIN 7 YL) 4 [4 (2 METHYLPHENYL)PIPERIDIN 1 YL] BUTAN 1 ONE; 1 (3 ACETYL 2,3,4,5 TETRAHYDRO 1H 3 BENZAZEPIN 7 YL) 4 [4 (3 METHYLPHENYL)PIPERIDIN 1 YL] BUTAN 1 ONE; 1 (3 ACETYL 2,3,4,5 TETRAHYDRO 1H 3 BENZAZEPIN 7 YL) 4 [4 (4 CHLOROPHENYL)PIPERIDIN 1 YL] BUTAN 1 ONE; 1 (3 ACETYL 2,3,4,5 TETRAHYDRO 1H 3 BENZAZEPIN 7 YL) 4 [4 (4 FLUOROPHENYL)PIPERIDIN 1 YL] BUTAN 1 ONE; 1 (3 ACETYL 2,3,4,5 TETRAHYDRO 1H 3 BENZAZEPIN 7 YL) 4 [4 (4 METHYLPHENYL)PIPERIDIN 1 YL] BUTAN 1 ONE; 1 (3 BENZOYL 2,3,4,5, TETRAHYDRO 1H 3 BENZAZEPIN 7 YL) 4 [4 (4 CHLOROPHENYL)PIPERIDIN 1 YL] BUTAN 1 ONE; 1 (3 BUTYRYL 2,3,4,5, TETRAHYDRO 1H 3 BENZAZEPIN 7 YL) 4 [4 (4 CHLOROPHENYL)PIPERIDIN 1 YL] BUTAN 1 ONE; 1 (5 ACETYL 4,5,6,7 TETRAHYDROTHIENOL[3,2 C]PYRIDIN 2 YL) 4 CHLOROBUTAN 1 ONE; 1 (5 ACETYL 4,5,6,7 TETRAHYDROTHIENOL[3,2 C]PYRIDIN 2 YL) 4 [4 (4 CHLOROPHENYL)PIPERIDIN 1 YL] BUTAN 1 ONE; 1 (6 ACETYL 4,5,6,7 TETRAHYDROTHIENOL[2,3 C]PYRIDIN 2 YL) 4 CHLOROBUTAN 1 ONE; 1 (6 ACETYL 4,5,6,7 TETRAHYDROTHIENOL[2,3 C]PYRIDIN 2 YL) 4 [4 (4 CHLOROPHENYL)PIPERIDIN 1 YL] BUTAN 1 ONE; 2,3,4,5 TETRAHYDRO 1H 3 BENZAZEPINE DERIVATIVE; 4 CHLORO 1 (6,7,8,9 TETRAHYDRO 5H BENZO[7]ANNULEN 2 YL) BUTAN 1 ONE; 4 [4 (4 CHLOROPHENYL)PIPERIDIN 1 YL] 1 (2,3,4,5 TETRAHYDRO 1H 3 BENZAZEPIN 7 YL) BUTAN 1 ONE DIHYDROCHLORIDE; 4 [4 (4 CHLOROPHENYL)PIPERIDIN 1 YL] 1 (3 METHYL 2,3,4,5 TETRAHYDRO 1H 3 BENZAZEPIN 7 YL) BUTAN 1 ONE; 4 [4 (4 CHLOROPHENYL)PIPERIDIN 1 YL] 1 (3 PENTANOYL 2,3,4,5 TETRAHYDRO 1H 3 BENZAZEPIN 7 YL) BUTAN 1 ONE; 4 [4 (4 CHLOROPHENYL)PIPERIDIN 1 YL] 1 (3 PROPIONYL 2,3,4,5 TETRAHYDRO 1H 3 BENZAZEPIN 7 YL) BUTAN 1 ONE; 4 [4 (4 CHLOROPHENYL)PIPERIDIN 1 YL] 1 [3 (CYCLOPROPYLCARBONYL) 2,3,4,5 TETRAHYDRO 1H 3 BENZAZEPIN 7 YL] BUTAN 1 ONE; 4 [4 (4 CHLOROPHENYL)PIPERIDIN 1 YL] 1 [3 (ETHYLSULFONYL) 2,3,4,5 TETRAHYDRO 1H 3 BENZAZEPIN 7 YL] BUTAN 1 ONE; 4 [4 (4 CHLOROPHENYL)PIPERIDIN 1 YL] 1 [3 (METHYLSULFONYL) 2,3,4,5 TETRAHYDRO 1H 3 BENZAZEPIN 7 YL] BUTAN 1 ONE; 7 [4 [4 (4 CHLOROPHENYL)PIPERIDIN 1 YL] BUTANOYL] N ETHYL 1,2,4,5 TETRAHYDRO 3H 3 BENZAZEPINE 3 CARBOXAMIDE; MELANIN CONCENTRATING HORMONE RECEPTOR 1 ANTAGONIST; METHYL 7 [4 [4 (4 CHLOROPHENYL)PIPERIDIN 1 YL] BUTANOYL] 1,2,4,5 TETRAHYDRO 3H 3 BENZAZEPINE 3 CARBOXYLATE; N [5 (4 CHLOROBUTANOYL) 2,3 DIHYDRO 1H INDEN 2 YL] ACETAMIDE; N [5 [4 [4 (4 CHLOROPHENYL)PIPERIDIN 1 YL]BUTANOYL] 2,3 DIHYDRO 1H INDEN 2 YL] ACETAMIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; AREA UNDER THE CURVE; ARTICLE; BINDING AFFINITY; BINDING SITE; CONTROLLED STUDY; DOSE RESPONSE; DRUG METABOLISM; DRUG STRUCTURE; DRUG SYNTHESIS; FISCHER 344 RAT; FOOD INTAKE; HUMAN; MAXIMUM PLASMA CONCENTRATION; NONHUMAN; OBESITY; RAT; STRUCTURE ACTIVITY RELATION;

RATTUS;

EID: 80054897458     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.09.007     Document Type: Article

References (41)

1. Kawauchi, H.; Kawazoe, I.; Tsubokawa, M.; Kishida, M.; Baker, B. I. Nature 1983, 305, 321.
2. Vaughan, J. M.; Fischer, W. H.; Hoeger, C.; River, J.; Vale, W. Endocrinology 1989, 125, 1660.
3. Presse, F.; Nahon, J. L.; Fischer, W. H.; Vale, W. Mol. Endocrinol. 1990, 4, 632.
4. Bittencourt, J. C.; Presse, F.; Arias, C.; Peto, C.; Vaughan, J.; Nahon, J. L.; Vale, W.; Sawchenko, P. E. J. Comp. Neurol. 1992, 319, 218.
5. Rossi, M.; Choi, J. S.; O'Shea, D.; Miyoshi, T.; Ghatei, M. A.; Bloom, S. R. Endocrinology 1997, 138, 351.
6. Qu, D.; Ludwig, D. S.; Gammeltoft, S.; Piper, M.; Pelleymounter, M. A.; Cullen, M. J.; Mathes, W. F.; Przypek, R.; Kanarek, R.; Maratos-Flier, E. Nature 1996, 380, 243.
7. Hanada, R.; Nakazato, M.; Matsukura, S.; Murakami, N.; Yoshimatsu, H.; Sakata, T. Biochem. Biophys. Res. Commun. 2000, 268, 88.
8. Sanchez, M.; Baker, B. I.; Celis, M. Peptides 1997, 18, 393;
9. Grill, H. J.; Ginsberg, A. B.; Seeley, R. J.; Kaplan, J. M. J. Neurosci. 1998, 18, 10128;
10. Ludwig, D. S.; Mountjoy, K. G.; Tatro, J. B.; Gillette, J. A.; Frederich, R. C.; Flier, J. S.; Maratos-Flier, E. Am. J. Physiol. 1998, 274, E627.
11. Shimada, M.; Tritos, N. A.; Lowell, B. B.; Flier, J. S.; Maratos-Flier, E. Nature 1998, 396, 670.
12. Ludwig, D. S.; Tritos, N. A.; Mastaitis, J. W.; Kulkarni, R.; Kokkotou, E.; Elmquist, J.; Lowell, B.; Flier, J. S.; Maratos-Flier, E. J. Clin. Invest. 2001, 107, 379.
13. Shimomura, Y.; Mori, M.; Sugo, T.; Ishibashi, Y.; Abe, M.; Kurokawa, T.; Onda, H.; Nishimura, O.; Sumino, Y.; Fujino, M. Biochem. Biophys. Res. Commun. 1999, 261, 622;
14. Chambers, J.; Ames, R. S.; Bergsma, D.; Muir, A.; Fitzgerald, L. R.; Hervieu, G.; Dytko, G. M.; Foley, J. J.; Martin, J.; Liu, W.-S.; Park, J.; Ellis, C.; Ganguly, S.; Konchar, S.; Cluderay, J.; Leslie, R.; Wilson, S.; Sarau, H. M. Nature 1999, 400, 261;
15. Saito, Y.; Nothacker, H.-P.; Wang, Z.; Lin, S. H. S.; Leslie, F.; Civelli, O. Nature 1999, 400, 265;
16. Lembo, P. M. C.; Grazzini, E.; Cao, J.; Hubatsch, D. A.; Pelletier, M.; Hoffert, C.; St-Onge, S.; Pou, C.; Labrecque, J.; Groblewski, T.; O'Donnell, D.; Payza, K.; Ahmad, S.; Walker, P. Nat. Cell Biol. 1999, 1, 267;
17. Bächner, D.; Kreienkamp, H.-J.; Weise, C.; Buck, F.; Richter, D. FEBS Lett. 1999, 457, 522.
18. Mori, M.; Harada, M.; Terao, Y.; Sugo, T.; Watanabe, T.; Shimomura, Y.; Abe, M.; Shintani, Y.; Onda, H.; Nishimura, O.; Fujino, M. Biochem. Biophys. Res. Commun. 2001, 283, 1013;
19. Hill, J.; Duckworth, M.; Murdock, P.; Rennie, G.; Sabido-David, C.; Ames, R. S.; Szekeres, P.; Wilson, S.; Bergsma, D. J.; Gloger, I. S.; Levy, D. S.; Chambers, J. K.; Muir, A. I. J. Biol. Chem. 2001, 276, 20125;
20. Sailer, A. W.; Sano, H.; Zeng, Z.; McDonald, T. P.; Pan, J.; Pong, S. S.; Feighner, S. D.; Tan, C. P.; Fukami, T.; Iwaasa, H.; Hreniuk, D. L.; Morin, N. R.; Sadowski, S. J.; Ito, M.; Ito, M.; Bansal, A.; Ky, B.; Figueroa, D. J.; Jiang, Q.; Austin, C. P.; MacNeil, D. J.; Ishihara, A.; Ihara, M.; Kanatani, A.; Van Der Ploeg, L. H.; Howard, A. D.; Liu, Q. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 7564;
21. An, S.; Cutler, G.; Zhao, J. J.; Huang, S. G.; Tian, H.; Li, W.; Liang, L.; Rich, M.; Bakleh, A.; Du, J.; Chen, J. L.; Dai, K. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 7576;
22. Rodriguez, M.; Beauverger, P.; Naime, I.; Rique, H.; Ouvry, C.; Souchaud, S.; Dromaint, S.; Nagel, N.; Suply, T.; Audinot, V.; Boutin, J. A.; Galizzi, J. P. Mol. Pharmacol. 2001, 60, 632;
23. Wang, S.; Behan, J.; O'Neill, K.; Weig, B.; Fried, S.; Laz, T.; Bayne, M.; Gustafson, E.; Hawes, B. E. J. Biol. Chem. 2001, 276, 34664.
24. Tan, C. P.; Sano, H.; Iwassa, H.; Pan, J.; Sailer, A. W.; Hreniuk, D. L.; Feighner, S. D.; Palyha, O. C.; Pong, S. S.; Figueroa, D. J.; Austin, C. P.; Jiang, M. M.; Yu, H.; Ito, J.; Ito, M.; Guan, X. M.; MacNeil, D. J.; Kanatani, A.; Van der Ploeg, L. H. T.; Howard, A. D. Genomics 2002, 79, 785.
25. Hervieu, G. J.; Cluderay, J. E.; Harrison, D.; Meakin, J.; Maycox, P.; Nasir, S.; Leslie, R. A. Eur. J. Neurosci. 2000, 12, 1194.
26. Kokkotou, E. G.; Tritos, N. A.; Mastaitis, J. W.; Slieker, L.; Maratos-Flier, E. Endocrinology 2001, 142, 680.
27. Chen, Y.; Hu, C.; Hsu, C.-K.; Zhang, Q.; Bi, C.; Asnicar, M.; Hsiung, H. M.; Fox, N.; Slieker, L. J.; Yang, D. D.; Heiman, M. L.; Shi, Y. Endocrinology 2002, 143, 2469;
28. Marsh, D. J.; Weingarth, D. T.; Novi, D. E.; Chen, H. Y.; Trumbauer, M. E.; Chen, A. S.; Guan, X.-M.; Jiang, M. M.; Feng, Y.; Camacho, R. E.; Shen, Z.; Frazier, E. G.; Yu, H.; Metzger, J. M.; Kuca, S. J.; Shearman, L. P.; Gopal-Truter, S.; MacNeil, D. J.; Strack, A. M.; MacIntyre, D. E.; Van der Ploeg, L. H.; Qian, S. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 3240.
29. Mashiko, S.; Ishihara, A.; Gomori, A.; Moriya, R.; Ito, M.; Iwaasa, H.; Matsuda, M.; Feng, Y.; Shen, Z.; Marsh, D. J.; Bednarek, M. A.; MacNeil, D. J.; Kanatani, A. Endocrinology 2005, 146, 3080;
30. Morens, C.; Nørregaard, P.; Receveur, J.-M.; Van Dijk, G.; Scheurink, A. J. W. Brain Res. 2005, 1062, 32.
31. Many articles and reviews were reported, including: Browning, A. Expert Opin. Ther. Patents 2004, 14, 1303;
32. Dyke, H. J.; Ray, N. C. Expert Opin. Ther. Patents 2005, 15, 1303;
33. Kowalski, T. J.; McBriar, M. D. Expert Opin. Investig. Drugs 2004, 13, 1113;
34. Johansson, A. Expert Opin. Ther. Patents 2011, 21, 905.
35. Takekawa, S.; Asami, A.; Ishihara, Y.; Terauchi, J.; Kato, K.; Shimomura, Y.; Mori, M.; Murakoshi, H.; Kato, K.; Suzuki, N.; Nishimura, O.; Fujino, M. Eur. J. Pharmacol. 2002, 438, 129.
36. MOE (The Molecular Operating Environment), version 2005.06; Chemical Computing Group Inc., 1010 Sherbrooke St. W, Suite 910 Montreal, Quebec, Canada H3A 2R7. www.chemcomp.com.
37. GOLD; CCDC, Business & Administration, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, U.K. http://www.ccdc.cam.ac.uk.
38. Jones, G.; Willett, P.; Glen, R. C. J. J. Mol. Biol. 1995, 245, 43.
39. Jones, G.; Willett, P.; Glen, R. C.; Leach, A. R.; Taylor, R. J. Mol. Biol. 1997, 267, 727.
40. Kamata, M.; Yamashita, T.; Imaeda, T.; Tanaka, T.; Terauchi, J.; Miyamoto, M.; Ora, T.; Tawada, M.; Endo, S.; Takekawa, S.; Asami, A.; Suzuki, N.; Nagisa, Y.; Nakano, Y.; Watanabe, K.; Ogino, H.; Kato, K.; Kato, K.; Ishihara, Y. Bioorg. Med. Chem. 2011, 19, 5539.
41. Palczewski, K.; Kumasaka, T.; Hori, T.; Behnke, C. A.; Motoshima, H.; Fox, B. A.; Le Trong, I.; Teller, D. C.; Okada, T.; Stenkamp, R. E.; Yamamoto, M.; Miyano, M. Science 2000, 289, 739.