Synthesis of new pyrrolo[1,2-a]quinoxalines: Potential non-peptide glucagon receptor antagonists

European Journal of Medicinal Chemistry

Volumn 33, Issue 4, 1998, Pages 293-308

  Guillon, Jean ^a   Dallemagne, Patrick ^a   Pfeiffer, Bruno ^b   Renard, Pierre ^b   Manechez, Dominique ^c   Kervran, Alain ^d   Rault, Sylvain ^a  

^a UNIVERSITÉ DE CAEN   (France)

^b ADIR   (France)

^c IRIS Institut de Recherches Internationales Servier   (France)

^d HÔPITAL ARNAUD DE VILLENEUVE   (France)

Author keywords

Diabetes; Glucagon receptor; Non peptide antagonist; Pyrrolo 1,2 a quinoxaline derivative

Indexed keywords

1 (2 AMINO 4 CHLOROPHENYL)PYRROLE; 1 (2 AMINO 4,5 DICHLOROPHENYL)PYRROLE; 1 (2 AMINOPHENYL)PYRROLE; 6,7 DICHLORO 2 [N (3 DIMETHYLAMINOPROPYL) N METHYLAMINO] 3 STYRYLQUINOXALINE; GLUCAGON RECEPTOR; PYRROLO[1,2 A]QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; DERIVATIZATION; DIABETES MELLITUS; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; GLUCONEOGENESIS; HORMONE SYNTHESIS; NONHUMAN; PEPTIDE SYNTHESIS; PROTEIN DOMAIN; RAT; RECEPTOR AFFINITY; SEQUENCE HOMOLOGY;

EID: 0032051611     PISSN: 02235234     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0223-5234(98)80063-9     Document Type: Article

References (47)

1. [1] Conlon J.M., Diabetologia 31 (1988) 563-566.
2. [2] Mojsov S., Kopczynski M.G., Habener J.F., J. Biol. Chem. 265 (1990) 8001-8008.
3. [3] Goodman Gilman A., Hardman J.G., Limbird L.E., Molinoff P.B., Ruddon R.W., The Pharmacological Basis of Therapeutics, 9th ed., Mc Graw-Hill, 1996.
4. [4] Kahn C.R., Weir G.C., Jeslin's Diabetes Mellitus, 3rd ed., Lea and Febiger, 1994.
5. [5] Harris R.A., Mapes J.P., Ochs R.S., Crabb D.W., Stropes L., Adv. Exp. Med. Biol. 111 (1979) 215-224.
6. [6] Jelinek L.J., Lok S., Rosenberg G.R., Smith R.A., Grant F.J., Biggs S., Bensch P.A., Kvijper J.L., Sheppard P.D., Sprecher C.A., O'hara P.J., Foster D., Walker K.M., Chen L.H.J., Mc Kernan P.A., Kindsvogel W., Science 259 (1993) 1614-1616.
7. [7] Unger R.H., Metabolism 27 (1978) 1691-1709.
8. [8] Unger R.H., Orci L., Lancet 1 (1975) 14-26.
9. [9] Unger R.H., Orci L., Arch. Intern. Med. 137 (1977) 482-491.
10. [10] Johnson D.G., Goebel C.U., Hruby V.J., Bregman M.D., Trivedi D., Science 215 (1982) 1115-1116.
11. [11] Collins J.L., Dambek P.J., Goldstein S.W., Faraci W.S., Bioorg. Med. Chem. Lett. 2(9) (1992) 915-918.
12. [12] Rault S., Lancelot J.C., Prunier H., Robba M., Renard P., Delagrange P., Pfeiffer B., Caignard D.H., Guardiola-Lemaître B., Hamon M., J. Med. Chem. 39 (1996) 2068-2080.
13. [13] Prunier H., Rault S., Lancelot J.C., Robba M., Renard P., Delagrange P., Pfeiffer B., Caignard D.H., Guardiola-Lemaître B., Hamon M., J. Med. Chem. 40 (1997) 1808-1819.
14. [14] Bureau R., Lancelot J.C., Prunier H., Rault S., Quant. Struct. Act. Relat. 15 (1996) 373-381.
15. [15] Clauson-Kaas N., Tyle Z., Acta Chem. Scand. 6 (1952) 667-670.
16. [16] Elming N., Clauson-Kaas N., Acta Chem. Scand. 6 (1952) 867-874.
17. [17] Ganem B., Osby J.O., Chem. Rev. 86 (1986) 763-780.
18. [18] Borah H.N., Prajapati D., Sandlu J.S., J. Chem. Res. Synop. 6 (1994) 228-229.
19. [19] Ren P.D., Pon S.F., Dong T.W., Wu S.H., Synth. Commun. 25(23) (1995) 3799-3803.
20. [20] Nagarajan K., Ranga Rao V., Venkateswarlu A., Indian J. Chem. 10 (1972) 344-350.
21. [21] Cheeseman G.W.H., Tuck B., Chem. Ind. 31 (1965) 1382.
22. [22] Cheeseman G.W.H., Tuck B., J. Chem. Soc. C (1966) 852-855.
23. [23] Gowenlock A.H., Newbold G.T., Spring E.S., J. Chem. Soc. (1945) 622-625.
24. [24] Cheeseman G.W.H., J. Chem. Soc. (1957) 3236-3239.
25. [25] Acheson R.M., J. Chem. Soc. (1956) 4731-4735.
26. [26] Haworth R.D., Robinson S., J. Chem. Suc. (1948) 777-782.
27. [27] Lancelot J.C., Gazengel J.M., Robba M., Chem. Pharm. Bull. 31(8) (1983) 2652-2661.
28. [28] Cheeseman G.W.H., Hawi A.A., Varvounis G., J. Heterocycl. Chem. 22 (1985) 423-427.
29. [29] Candy C.F., Jones R.A., Wright P.H., J. Chem. Soc. C (1970) 2563-2567.
30. [30] Dallemagne P., Rault S., Fabis F., Dumoulin H., Robba M. Heterocycl. Commun. 1(1) (1994) 23-25.
31. [31] Nacci V., Campiani G., Garofalo A., Synth. Commun. 20(19) (1990) 3019-3029.
32. [32] Oussaid B., Hubert C., Fayet J.P., Garrigues B., Bull. Soc. Chim. Fr. 130 (1993) 86-92.
33. [33] Layer R.W., Chem. Rev. 63 (1963) 489-510.
34. [34] Schenker E., Angew. Chem. 73(3) (1961) 106.
35. [35] Dallemagne P., Rault S., Fabis F., Dumoulin H., Robba M., Synth. Commun. 24(13) (1994) 1855-1857.
36. [36] Von Auwers K., Ber. 50 (1917) 1177-1182.
37. [37] Berlin A., Martina S., Pugani G., Schiavon G., Zotti G., Heterocycles 32(1) (1991) 85-92.
38. [38] Blache Y., Gueiffier A., Chavignon O., Teulade J.C., Milhavet J.C., Viols H., Chapat J.P., Dauphin G., J. Heterocycl. Chem. 31 (1994) 161-166.
39. [39] Blache Y., Gueiffier A., Elhakmaoui A., Viols H., Chapat J.P., Chavignon O., Teulade J.C., Grassy G., Dauphin G., Carpy A., J. Heterocycl. Chem. 32 (1995) 1317-1324.
40. [40] Nystrom R.F., Brown W.G., J. Am. Chem. Soc. 69 (1947) 1197-1199.
41. [41] Bandaranayake W.M., Crombie L., Whiting D.A., J. Chem. Soc. C (1971) 811-815.
42. [42] Alazard J.P., Bové O., Gillet B., Guénard D., Beloeil J.C., Thal C., Bull. Soc. Chim. Fr. 130 (1993) 779-787.
43. [43] Gros L., Demirpence E., Jarrouse C., Kervran A., Bataille D., Endocrinology 130 (1992) 1263-1270.
44. [44] Dornauer H., Anderson V.B., US patent 3, 939, 159; Chem. Abstr. 84 (1976) 180293p.
45. [44] Dornauer H., Anderson V.B., US patent 3, 939, 159; Chem. Abstr. 84 (1976) 180293p.
46. [45] Gazdar A.F., Chick L.W., Die H.K., Sims H.L., King D.L., Weir J.C., Lauris V., Proc. Natl. Acad. Sci. USA 77 (1980) 3519-3523.
47. [46] Neville Jr D.M. Biochim. Biophys. Acta 154 (1968) 540-552.