Erratum: Discovery of DF-461, a potent squalene synthase inhibitor (ACS Medicinal Chemistry Letters (2013) 4:10 (932-936) DOI:10.1021/ml400151c);Discovery of DF-461, a potent squalene synthase inhibitor

ACS Medicinal Chemistry Letters

Volumn 4, Issue 10, 2013, Pages 932-936

  Ichikawa, Masanori ^a   Ohtsuka, Masami ^a   Ohki, Hitoshi ^a   Ota, Masahiro ^a   Haginoya, Noriyasu ^a   Itoh, Masao ^a   Shibata, Yoshihiro ^a   Sugita, Kazuyuki ^a   Ishigai, Yutaka ^a   Terayama, Koji ^a   Kanda, Akira ^a   Usui, Hiroyuki ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

dyslipidemia; inhibitor; Squalene synthase; triazolobenzoxazepine

Indexed keywords

2 CHLORO 3 METHOXYPHENYL; 2 METHYL 3 METHOXYPHENYL; 2,3 DIMETHOXYPHENYL; ATORVASTATIN; CHOLESTEROL; DF 461; LAPAQUISTAT; SQUALENE SYNTHASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ARTICLE; CHOLESTEROL LIVER LEVEL; CHOLESTEROL SYNTHESIS; CONTROLLED STUDY; DRUG EFFICACY; DRUG IDENTIFICATION; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; IC 50; IN VIVO STUDY; NONHUMAN; PRIORITY JOURNAL; RAT; SINGLE DRUG DOSE; STRUCTURE ACTIVITY RELATION;

RATTUS;

EID: 84885444378     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml500149q     Document Type: Erratum

References (23)

1. Tobert, J. A. Losvastatin and beyond: the history of the HMG-CoA reductase inhibitor Nat. Rev. Drug. Discovery 2003, 2, 517-526
2. Havel, R. J.; Rapaport, E. Management of primary hyperlipidemia New Eng. J. Med. 1995, 332, 1491-1498
3. Shepherd, J.; Cobbe, S. M.; Ford, I.; Isles, C. G.; Lorimer, A. R.; Macfarlane, P. W.; McKillop, J. H.; Packard, C. J. Prevention of coronary heart disease with pravastatin in men with hypercholesterolemia N. Engl. J. Med. 1995, 333, 1301-1308
4. Hodel, C. Myopathy and rhabdomyolysis with lipid-lowering drugs Toxicol. Lett. 2002, 128, 159-168
5. Thompson, P. D.; Clarkson, P.; Karas, R. H. Statin-associated myopathy JAMA. 2003, 289, 1681-1690
6. Furberg, C. D.; Pitt, B. Withdrawal of cerivastatin from the world market Curr. Control Trials Cardiovasc. Med. 2001, 2, 205-207
7. Ishihara, T.; Kakuta, H.; Moritani, H.; Ugawa, T.; Yanagisawa, I. Synthesis and biological evaluation of novel propylamine derivatives as orally active squalene synthase inhibitors Bioorg. Med. Chem. 2004, 12, 5899-5908
8. Miki, T.; Kori, M.; Mabuchi, H.; Tozawa, R.; Nishimoto, T.; Sugiyama, Y.; Teshima, K.; Yukimasa, H. Synthesis of novel 4,1-benzoxazepine derivatives as squalene synthase inhibitors and their inhibition of cholesterol synthesis J. Med. Chem. 2002, 45, 4571-4580
9. Biller, S. A.; Neuenschwander, K.; Ponpipom, M. M.; Poulter, C. D. Squalene synthase inhibitors Curr. Pharm. Des. 1996, 2, 1-40
10. Gonzalez-Pacanowska, D.; Arison, B.; Havel, C. M.; Watson, J. A. Isopentenoid synthesis in isolated embryonic Drosophila cells. Farnesol catabolism and ω-oxidation J. Biol. Chem. 1988, 263, 1301-1306
11. Bergstrom, J. D.; Kurtz, M. M.; Rew, D. J.; Amend, A. M.; Karakas, J. D.; Bostedor, R. G.; Bansal, V. S.; Dufresne, C.; VanMiddlesworth, F. L.; Hensens, O. D. Zaragozic acids: a family of fungal metabolites that are picomolar competitive inhibitors of squalene synthase Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 80-84
12. Bostedor, R. G.; Karkas, J. D.; Arison, B. H.; Bansal, V. S.; Vaidya, S.; Germershausen, J. I.; Kurtz, M. M.; Bergstrom, J. D. Farnesol-derived dicarboxylic acids in the urine of animals treated with zaragozic acid A or with farnesol J. Biol. Chem. 1997, 272, 9197-9203
13. Griebenow, N.; Flessner, T.; Buchmueller, A.; Raabe, M.; Bischoff, H.; Kolkhof, P. Identification and optimization of tetrahydro-2 H -3-benzazepin-2-ones as squalene synthase inhibitors Bioorg. Med. Chem. Lett. 2011, 21, 2554-2558
14. Griebenow, N.; Buchmueller, A.; Kolkhof, P.; Schamberger, J.; Bischoff, H. Identification of 4 H,6 H -[2]benzoxepino[4,5-c][1,2]oxazoles as novel squalene synthase inhibitors Bioorg. Med. Chem. Lett. 2011, 21, 3648-3653
15. Hiyoshi, H.; Yanagimachi, M.; Ito, M.; Saeki, T.; Yoshida, I.; Okada, T.; Ikuta, H.; Shinmyo, D.; Tanaka, K.; Kurusu, N.; Tanaka, H. Squalene synthase inhibitors reduce plasma triglyceride through a low-density lipoprotein receptor-independent mechanism Eur. J. Pharmacol. 2001, 431, 345-352
16. Brown, G. R.; Clarke, D. S.; Foubister, A. J.; Freeman, S.; Harrison, P. J.; Johnson, M. C.; Mallion, K. C.; McCormick, J.; McTaggart, F.; Reid, A. C.; Smith, G. J.; Taylor, M. J. Synthesis and activity of a novel series of 3-biarylquinuclidine squalene synthase inhibitors J. Med. Chem. 1996, 39, 2971-2979
17. Usui, H.; Kagechika, K.; Nagashima, H. WO1998/029380.
18. Usui, H.; Katakura, S.; Suzuki, M. Jpn. Kokai Tokkyo Koho. 2001, 131 p (JP 2001/354587).
19. Ichikawa, M.; Yokomizo, A.; Itoh, M.; Sugita, K.; Usui, H.; Shimizu, H.; Suzuki, M.; Terayama, K.; Kanda, A. Discovery of a new 2-aminobenzhydrol template for highly potent squalene synthase inhibitors Bioorg. Med. Chem. 2011, 19, 1930-1949
20. Ichikawa, M.; Yokomizo, A.; Itoh, M.; Haginoya, N.; Sugita, K.; Usui, H.; Terayama, K.; Kanda, A. Discovery of atrop fixed alkoxy-aminobenzhydrol derivatives: Novel, highly potent and orally efficacious squalene synthase inhibitors Bioorg. Med. Chem. 2011, 19, 5207-5224
21. Ichikawa, M.; Ohtsuka, M.; Ohki, H.; Ota, M.; Haginoya, N.; Itoh, M.; Sugita, K.; Usui, H.; Suzuki, M.; Terayama, K.; Kanda, A. Discovery of novel tricyclic compounds as squalene synthase inhibitors Bioorg. Med. Chem. 2012, 20, 3072-3093
22. Pfefferkorn, J. A.; Litchfield, J.; Hutchings, R.; Cheng, X. M.; Larsen, S. D.; Auerbach, B.; Bush, M. R.; Lee, C.; Erasga, N.; Bowles, D. M.; Boyles, D. C.; Lu, G.; Sekerke, C.; Askew, V.; Hanselman, J. C.; Dillon, L.; Lin, Z.; Robertson, A.; Olsen, K.; Boustany, C.; Atkinson, K.; Goosen, T. C.; Sahasrabudhe, V.; Chupka, J.; Duignan, D. B.; Feng, B.; Scialis, R.; Kimoto, E.; Bi, Y. A.; Lai, Y.; El-Kattan, A.; Bakker-Arkema, R.; Barclay, P.; Kindt, E.; Le, V.; Mandema, J. W.; Milad, M.; Tait, B. D.; Kennedy, R.; Trivedi, B. K.; Kowala, M. Discovery of novel hepatoselective HMG-CoA reductase inhibitors for treating hypercholesterolemia: A bench-to-bedside case study on tissue selective drug distribution Bioorg. Med. Chem. Lett. 2011, 21, 2725-2731
23. Shechter, I.; Klinger, E.; Rucker, M. L.; Engstrom, R. G.; Spirito, J. A.; Islam, M. A.; Boettcher, B. R.; Weinstein, D. B. Solubilization, purification, and characterization of a truncated form of rat hepatic squalene synthetase J. Biol. Chem. 1992, 267, 8628-8635