The process development of RG 12525 (2-{[4-(Tetrazol-5-ylmethylphenyl)-methoxy]phenoxymethyl}quinoline)

Organic Process Research and Development

Volumn 5, Issue 1, 2001, Pages 9-15

  Bridge, Andrew W ^a,b   Jones, Ronald H ^a   Kabir, Humayun ^a   Kee, Alex A ^a   Lythgoe, David J ^a   Nakach, Mustafa ^a,c   Pemberton, Clive ^a   Wrightman, John A ^a  

^a Aventis Pharma Ltd   (United Kingdom)

^b SANOFI   (France)

^c Centre de Recherche de Vitry Alfortville   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0035625139     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op0000677     Document Type: Article

References (17)

1. Formerly known as Rhône-Poulenc Rorer Ltd.
2. Huang, Fu-Chih; Galemmo, Robert A.; Johnson, William H., Jr.; Poli, Gregory B., Jr.; Morrisette, Matthew M.; Mencel, James J.; Warus, James D.; Campbell, Henry F.; Nuss, George W.; Carnathan, Gilbert W.; Van Inwegen, Richard G. J. Med. Chem. 1990, 33, 3, 1194-1200
3. Jayyosi, Zaid; McGeehan, Gerard M.; Kelley, Michael F. PPAR-g-binding quinoline derivatives, their preparation, and their therapeutic use. PCT Int. Appl. 1999, 125 pp. CODEN: PIXXD2 WO 9920275 A1 19990429 CAN 130:320864 AN 1999: 282096.
4. O'Brien, M. K.; Sledeski, A. W.; Truesdale, L. K. Tetrahedron Lett. 1997, 38, 509-512; Sledeski, A. W.; O'Brien, M. K.; Truesdale, L. K. Tetrahedron Lett. 1997, 38, 1129-1132.
5. O'Brien, M. K.; Sledeski, A. W.; Truesdale, L. K. Tetrahedron Lett. 1997, 38, 509-512; Sledeski, A. W.; O'Brien, M. K.; Truesdale, L. K. Tetrahedron Lett. 1997, 38, 1129-1132.
6. (a) Thompson, M. D.; Authelin, J.-R. Chemical Development of the Drug Substance Solid Form. In Process Chemistry in the Pharmaceutical Industry; Gadamasetti, K. G., Ed.; Marcel-Dekker: New York, 1999; p 371-388; ISBN 0-8247-1981-6.
7. (b) Carlton, R. A.; Difeo, T. J.; Powner, T. H.; Santos, I.; Thompson, M. D. J. Pharm. Sci. 1996, 85, 461-467.
8. Mathes, W.; Schüly, H. Angew. Chem., Int. Ed. Engl. 1963, 2, 144.
9. Nakanishi, S.; Saito, T. (Sumika Fine Chemicals Co. Ltd.). Jpn. Kokai Tokkyo, Koho JP 92-360753, 1994.
10. Hain, J.; McGee, H. A. Ind. Eng. Chem. Prod. Res. Dev. 1984, 23, 490.
11. Department of the Environment, Transport and the Regions, Greening Government Operations available from http://www.environment.detr.gov.uk/ greening/greenpro/gguide/gg2annc.htm.
12. Based on isolated yields.
13. MODDE is a registered trademark of UMETRI AB, Box 7960, S-907 19 Umeå, Sweden.
14. The relationship between the kinetic data of the low-temperature thermolysis and the heats of explosion of inorganic azides. Zeman, Svatopluk; Dimun, Milan; Truchlik, Stefan; Kabatova, Viera. Thermochim. Acta 1984, 80 (1), 137-41.
15. Colour as determined by solution colour; Y6 or higher was acceptable.
16. Of this quantity 3.03 g was collected in a sodium hypochlorite trap so that only 17.27 g of chlorine (243 mmol, 1.39 equiv) is required for reaction.
17. The isolated yield represents 86.5%; the assay of the material is 87.6%; hence, corrected yield = 86.5 x 0.876 = 75.7%