Synthesis of three isotopically labeled versions and a metabolite of Aurora A kinase inhibitor

Journal of Labelled Compounds and Radiopharmaceuticals

Volumn 52, Issue 9, 2009, Pages 355-359

  Li, Yuexian ^a   Prakash, Shimoga R ^a  

^a MILLENNIUM PHARMACEUTICALS INC   (United States)

Author keywords

Sodium carboxyl 14C 4 9 chloro 7 (2,6 difluorophenyl) 5H pyrimido 5,4 d 2 benzazepin 2 yl amino benzoate; Sodium ring 14C 4 9 chloro 7 (2,6 difluorophenyl) 5H pyrimido 5,4 d 2 benzazepin 2 yl amino benzoate; 14C 4 guanidinobenzoic acid; D4, 15N 4 guanidinobenzoic acid; D4, 15N 4 9 chloro 7 (2,6 difluorophenyl) 5H pyrimido 5,4 d 2 benzazepin 2 yl amino benzoic acid; acyl glucuronide of 4 9 chloro 7 (2,6 difluorophenyl) 5H pyrimido 5,4 d 2 benzazepin 2 yl amino benzoic acid

Indexed keywords

AMINO ACIDS; BENZOIC ACID; CARBOXYLATION; ENZYME INHIBITION; METABOLITES;

DIFLUOROPHENYL; GLUCURONIDES; SODIUM CARBOXYL-[ 14C]-4-[[9-CHLORO-7-(2,6-DIFLUOROPHENYL)-5H-PYRIMIDO[5,4-D][2] BENZAZEPIN-2-YL]AMINO]-BENZOATE; SODIUM RING-[14C]-4-[[9-CHLORO-7-(2,6-DIFLUOROPHENYL)-5H- PYRIMIDO[5,4-D][2]BENZAZEPIN-2-YL]AMINO]-BENZOATE; [14C]-4-GUANIDINOBENZOIC ACID; [D4, 15N]-4-GUANIDINOBENZOIC ACID; [D4, 15N]-4-[[9-CHLORO-7- (2,6-DIFLUOROPHENYL)-5H-PYRIMIDO[5,4-D][2]BENZAZEPIN-2-YL]AMINO]-BENZOIC ACID; Β-ACYL GLUCURONIDE OF 4-[[9-CHLORO-7-(2,6-DIFLUOROPHENYL)-5H-PYRIMIDO[5,4- D][2]BENZAZEPIN-2-YL]AMINO]-BENZOIC ACID;

SODIUM;

4 AMINOBENZOIC ACID; 4 GUANIDINOBENZOIC ACID; 4 [[9 CHLORO 7 (2,6 DIFLUOROPHENYL) 5H PYRIMIDO[5,4 D][2]BENZAZEPIN 2 YL]AMINO]BENZOIC ACID; 4 [[9 CHLORO 7 (2,6 DIFLUOROPHENYL) 5H PYRIMIDO[5,4 D][2]BENZAZEPIN 2 YL]AMINO]BENZOIC ACID BETA ACYL GLUCURONIDE; 4 [[9 CHLORO 7 (2,6 DIFLUOROPHENYL) 5H PYRIMIDO[5,4 D][2]BENZAZEPIN 2 YL]AMINO]BENZOIC ACID N 15; ANTINEOPLASTIC AGENT; AURORA A KINASE; BENZOIC ACID DERIVATIVE; CARBON 14; CYANAMIDE; CYANAMIDE C 14; DRUG METABOLITE; GLUCURONIC ACID; GLUCURONIDE; NITROGEN 15; PROTEIN SERINE THREONINE KINASE INHIBITOR; SODIUM CARBOXYL 4 [[9 CHLORO 7 (2,6 DIFLUOROPHENYL) 5H PYRIMIDO[5,4 D][2]BENZAZEPIN 2 YL]AMINO]BENZOIC ACID C 14; SODIUM RING 4 [[9 CHLORO 7 (2,6 DIFLUOROPHENYL) 5H PYRIMIDO[5,4 D][2]BENZAZEPIN 2 YL]AMINO]BENZOIC ACID C 14; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; GLUCURONIDATION; ISOTOPE LABELING; RADIOCHEMISTRY;

EID: 68949161040     PISSN: 03624803     EISSN: 10991344     Source Type: Journal    
DOI: 10.1002/jlcr.1607     Document Type: Article

References (10)

1. K. Hoar, A. Chakravarty, C. Rabino, D. Wysong, D. Bowman, N. Roy, J. A. Ecsedy, Mol. Cell. Biol. 2007, 27, 4513-4525.
2. P. J. LeRoy, J. J. Hunter, K. M. Hoar, K. E. Burke, V. Shinde, J. Ruan, D. Bowman, K. Galvin, J. A. Ecsedy, Cancer Res. 2007, 67, 5362-5370.
3. M. G. Manfredi, J. A. Ecsedy, K. A. Meetze, S. K. Balani, O. Burenkova, E. Chen, K. M. Galvin, K. M. Hoar, J. J. Huck, P. J. LeRoy, E. T. Ray, T. B. Sells, B. Stringer, S. G. Stroud, T. J. Vos, G. S. Weatherhead, D. R. Wysong, M. Z. Zhang, J. B. Bolen, C. F. Claiborne, Proc. Natl. Acad. Sci. 2007, 104, 4106-4111.
4. C. F. Claiborne, L. J. Payne, R. J. Boyce, T. B. Sells, S. G. Stroud, S. Travers, T. J. Vos, G. S. Weatherhead, US Pat. Appl. Publ. 2005, US 256102.
5. Account of this work was presented at the 6th International Conference on Isotopes, Seoul, Korea, 12-16 May, 2008.
6. A. Miller, J. J. Bischoff, Synthesis 1986, 777-779.
7. A. H. Binham, R. J. Davenport, L. Gowers, R. L. Knight, C. Lowe, D. A. Owen, D. M. Parry, W. R. Pitt, Bioorg. Med. Chem. Lett. 2004, 14, 409-412.
8. A. D. Mesmaeker, P. Hoffmann, B. Ernst, Tetrahedron Lett. 1989, 30, 3773-3776.
9. H. Juteau, Y. Gareau, M. Labelle, Tetrahedron Lett. 1997, 38, 1481-1484.
10. J. A. Perrie, J. R. Harding, D. W. Holt, A. Johnston, P. Meath, A. V. Stachulski, Org. Lett. 2005, 7, 2591-2594.