Preparation of novel 2,3,8-trisubstituted pyrido[3,4-b]pyrazines and pyrido[2,3-b]pyrazines

Synthesis

Volumn , Issue 5, 2011, Pages 794-806

  Antoine, Maud ^a   Czech, Michael ^b   Gerlach, Matthias ^b   Günther, Eckhard ^b   Schuster, Tilmann ^b   Marchand, Pascal ^a  

^a UNIVERSITÉ DE NANTES   (France)

^b Æterna Zentaris GmbH   (Germany)

Author keywords

amide; di amino pyridine; pyrido 2,3 b pyrazine; pyrido 3,4 b pyrazine; thiourea; urea

Indexed keywords

AMIDES; METABOLISM; UREA;

FOUR-STEP SYNTHESIS; PYRAZINES; PYRIDO[2 ,3-B]; PYRIDO[2 ,3-B]PYRAZINE; SYNTHETIC ROUTES;

THIOUREAS;

AMIDE; ANILINE; N (2,3 DIPHENYLPYRIDO[2,3 B]PYRAZIN 8 YL) N' ETHYLTHIOUREA; N (2,3 DIPHENYLPYRIDO[2,3 B]PYRAZIN 8 YL) N' ETHYLUREA; N (2,3 DIPHENYLPYRIDO[2,3 B]PYRAZIN 8 YL) N' PHENYLUREA; N (2,3 DIPHENYLPYRIDO[3,4 B]PYRAZIN 8 YL) 4 METHOXYBENZAMIDE; N (2,3 DIPHENYLPYRIDO[3,4 B]PYRAZIN 8 YL) N' (3 METHOXYPHENYL)UREA; N (2,3 DIPHENYLPYRIDO[3,4 B]PYRAZIN 8 YL) N' ETHYLTHIOUREA; N (2,3 DIPHENYLPYRIDO[3,4 B]PYRAZIN 8 YL) N' ETHYLUREA; N (2,3 DIPHENYLPYRIDO[3,4 B]PYRAZIN 8 YL) N' PHENYLUREA; N (2,3 DIPHENYLPYRIDO[3,4 B]PYRAZIN 8 YL)ACETAMIDE; N (3 BROMOPHENYL) 2,3 DIPHENYLPYRIDO[3,4 B]PYRAZIN 8 AMINE; N (3 CHLORO 4 FLUOROPHENYL) 2,3 DIPHENYLPYRIDO[3,4 B]PYRAZIN 8 AMINE; N (3 CHLOROPHENYL) N' (2,3 DIPHENYLPYRIDO[2,3 B]PYRAZIN 8 YL)UREA; N (3 CHLOROPHENYL) N' (2,3 DIPHENYLPYRIDO[3,4 B]PYRAZIN 8 YL)UREA; N [2,3 BIS(4 METHOXYPHENYL)PYRIDO[2,3 B]PYRAZIN 8 YL] N' ETHYLUREA; N [2,3 BIS(4 METHOXYPHENYL)PYRIDO[2,3 B]PYRAZIN 8 YL] N' PHENYLUREA; N [2,3 BIS(4 METHOXYPHENYL)PYRIDO[3,4 B]PYRAZIN 8 YL] N' ETHYLTHIOUREA; N [2,3 BIS(4 METHOXYPHENYL)PYRIDO[3,4 B]PYRAZIN 8 YL] N' PHENYLUREA; N [2,3 BIS(4 METHOXYPHENYL)PYRIDO[3,4 B]PYRAZIN 8 YL]ACETAMIDE; N [4 CHLORO 3 (TRIFLUOROMETHYL)PHENYL] N' (2,3 DIPHENYLPYRIDO[3,4 B]PYRAZIN 8 YL)UREA; PYRAZINE DERIVATIVE; THIOUREA; UNCLASSIFIED DRUG; UREA;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 79951851741     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1259429     Document Type: Article

References (25)

1. Koch P, Jahns H, Schattel V, Goettert M, Laufer S, J. Med. Chem. 2010 53 1128
2. Claus E, Seipelt I, Günther E, Polymeropoulos E, Czech M, Schuster T, WO 2007,054,556 2007; Chem. Abstr. 2007, 146, 521825
3. Wrasidlo W, Doukas J, Royston I, Noronha G, Hood J D., Dneproskaia E, Gong X, Splittgerber U, Zhao N, WO 2004,030,635 2004; Chem. Abstr. 2004, 140, 321386
4. White L E., Reynolds R C., Suling W, WO 2004,005,472 2004; Chem. Abstr. 2004, 140, 105238
5. Crowley P J., Müller U, Dobler M, Williams J, WO 2005,123,733 2005; Chem. Abstr. 2005, 144, 88319
6. Palanki M S. S., Dneprovskaia E, Doukas J, Fine R M., Hood J, Kang X, Lohse D, Martin M, Noronha G, Soll R M., Wrasidlo W, Yee S, Zhu H, J. Med. Chem. 2007 50 4279
7. Friedrich K, In Houben-Weyl 4th ed., Vol. E9c Schaumann E Georg Thieme Verlag Stuttgart 1998 227
8. Temple C, Rener G A., J. Med. Chem. 1990 33 3044
9. Temple C, Rose J D., Elliot R D., Montgomery J A., J. Med. Chem. 1970 13 853
10. Israel M, Day A R., J. Org. Chem. 1959 24 1455
11. Brzozka L, Baran W, Kraus W, Tomasck P, Polish J. Chem. 1995 69 605
12. Deady L W., Grimmet M R., Potts C H., Tetrahedron 1979 35 2895
13. Deady L W., Korytsky O L., Rowe J E., Aust. J. Chem. 1982 35 2025
14. Wieczorek J S., Talik T, Rocz. Chem. 1962 36 967
15. Harris M G., Stewart R, Can. J. Chem. 1977 55 380
16. Yang B H., Buchwald S L., J. Organomet. Chem. 1999 576 125
17. Prashad M, Hu B, Lu Y, Draper K, Har D, Repic O, Blacklock T J., J. Org. Chem. 2000 65 2612
18. Li H, Wang Y, Yan L, Campbell R M., Anderson B D., Wagner J R., Yingling J M., Bioorg. Med. Chem. Lett. 2004 14 3585
19. Wolfe J P., Ahman J, Sadighi J P., Singer R A., Buchwald S L., Tetrahedron Lett. 1997 38 6367
20. Graboyes H, Day A R., J. Am. Chem. Soc. 1957 79 6421
21. Temple C, Laseter A G., Rose J D., Montgomery J A., J. Heterocycl. Chem. 1970 7 1195
22. Cai S X., Huang J C., Espitia S A., Tran M, Ilyin V I., Hawkinson J E., Woodward R M., Weber E, Keana J F. W., J. Med. Chem. 1997 40 3679
23. Zhao Z, Wisnoski D D., Wolkenberg S E., Leister W H., Wang Y, Lindsley C W., Tetrahedron Lett. 2004 45 4873
24. Yeo B R., Hallett A J., Kariuki B M., Pope S J. A., Polyhedron 2010 29 1088
25. Scriven E F. V., Turnbull K, Chem. Rev. 1988 88 297