Synthesis of 5-N-Substituted Tetrazole Derivatives of the Potent NK1 Receptor Antagonist GR203040

Synlett

Volumn 1996, Issue 4, 1996, Pages 359-360

  Congreve, Miles S ^a  

^a GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007312451     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5420     Document Type: Article

References (22)

1. Regoli, D.; Boudon, A.; Fauchere, J.-L. Pharmacological Reviews, 1994, 46, 551-599.
2. Ward, P.; Armour, D. R.; Bays, D. E.; Evans, B.; Giblin, G. M. P.; Heron, N.; Hubbard, T.; Liang K.; Middlemiss, D.; Mordaunt J.; Naylor, N.; Pegg, N. A.; Vinader, M. V.; Watson, S. P.; Bountra, C.; Evans, D. C. J. Med Chem., 1995, 38, 4985-92.
3. Ishii, K.; Hatanaka, M.; Ueda, I. Chem. Pharm. Bull., 1991, 39, 3331-3334; Miller, A. E.; Feeney, D. J.; Ma, Y.; Zarcone, L.; Aziz, M. A.; Magnuson, E. Synth. Commun., 1990, 20, 217-226; Atherton, F. R.; Lambert, R. W. Tetrahedron. 1983, 39, 2599-2608; Ding, Y. X.; Weber, W. P., Synthesis, 1987, 823-824; Mironova, D. F.; Staninets, V. I. Ukr. Khim. Zh., 1986, 52, 1269-1273; Zbiral, E.; Schoerkhuber, W. Liebigs Ann. Chem., 1982, 1870-1890; Tsuge, O.; Urano, S.; Oe, K. J. Org Chem., 1980, 45, 5130-5136; Yamamoto, I.; Tokanou, H.; Uemura, H.; Gotoh, H. J. Chem. Soc., Perkin Trans. 1, 1977, 1241-1243; Imhof, R.; Ladner, D. W.; Muchowski, J. M. J. Org Chem., 1977, 42, 3709-3713; Viehe, H. G.; George, P. Chimia, 1975, 29, 209-210; Kauer, J. C.; Sheppard, W. A. J. Org. Chem., 1967, 32, 3580-3593.
4. Ishii, K.; Hatanaka, M.; Ueda, I. Chem. Pharm. Bull., 1991, 39, 3331-3334; Miller, A. E.; Feeney, D. J.; Ma, Y.; Zarcone, L.; Aziz, M. A.; Magnuson, E. Synth. Commun., 1990, 20, 217-226; Atherton, F. R.; Lambert, R. W. Tetrahedron. 1983, 39, 2599-2608; Ding, Y. X.; Weber, W. P., Synthesis, 1987, 823-824; Mironova, D. F.; Staninets, V. I. Ukr. Khim. Zh., 1986, 52, 1269-1273; Zbiral, E.; Schoerkhuber, W. Liebigs Ann. Chem., 1982, 1870-1890; Tsuge, O.; Urano, S.; Oe, K. J. Org Chem., 1980, 45, 5130-5136; Yamamoto, I.; Tokanou, H.; Uemura, H.; Gotoh, H. J. Chem. Soc., Perkin Trans. 1, 1977, 1241-1243; Imhof, R.; Ladner, D. W.; Muchowski, J. M. J. Org Chem., 1977, 42, 3709-3713; Viehe, H. G.; George, P. Chimia, 1975, 29, 209-210; Kauer, J. C.; Sheppard, W. A. J. Org. Chem., 1967, 32, 3580-3593.
5. Ishii, K.; Hatanaka, M.; Ueda, I. Chem. Pharm. Bull., 1991, 39, 3331-3334; Miller, A. E.; Feeney, D. J.; Ma, Y.; Zarcone, L.; Aziz, M. A.; Magnuson, E. Synth. Commun., 1990, 20, 217-226; Atherton, F. R.; Lambert, R. W. Tetrahedron. 1983, 39, 2599-2608; Ding, Y. X.; Weber, W. P., Synthesis, 1987, 823-824; Mironova, D. F.; Staninets, V. I. Ukr. Khim. Zh., 1986, 52, 1269-1273; Zbiral, E.; Schoerkhuber, W. Liebigs Ann. Chem., 1982, 1870-1890; Tsuge, O.; Urano, S.; Oe, K. J. Org Chem., 1980, 45, 5130-5136; Yamamoto, I.; Tokanou, H.; Uemura, H.; Gotoh, H. J. Chem. Soc., Perkin Trans. 1, 1977, 1241-1243; Imhof, R.; Ladner, D. W.; Muchowski, J. M. J. Org Chem., 1977, 42, 3709-3713; Viehe, H. G.; George, P. Chimia, 1975, 29, 209-210; Kauer, J. C.; Sheppard, W. A. J. Org. Chem., 1967, 32, 3580-3593.
6. Ishii, K.; Hatanaka, M.; Ueda, I. Chem. Pharm. Bull., 1991, 39, 3331-3334; Miller, A. E.; Feeney, D. J.; Ma, Y.; Zarcone, L.; Aziz, M. A.; Magnuson, E. Synth. Commun., 1990, 20, 217-226; Atherton, F. R.; Lambert, R. W. Tetrahedron. 1983, 39, 2599-2608; Ding, Y. X.; Weber, W. P., Synthesis, 1987, 823-824; Mironova, D. F.; Staninets, V. I. Ukr. Khim. Zh., 1986, 52, 1269-1273; Zbiral, E.; Schoerkhuber, W. Liebigs Ann. Chem., 1982, 1870-1890; Tsuge, O.; Urano, S.; Oe, K. J. Org Chem., 1980, 45, 5130-5136; Yamamoto, I.; Tokanou, H.; Uemura, H.; Gotoh, H. J. Chem. Soc., Perkin Trans. 1, 1977, 1241-1243; Imhof, R.; Ladner, D. W.; Muchowski, J. M. J. Org Chem., 1977, 42, 3709-3713; Viehe, H. G.; George, P. Chimia, 1975, 29, 209-210; Kauer, J. C.; Sheppard, W. A. J. Org. Chem., 1967, 32, 3580-3593.
7. Ishii, K.; Hatanaka, M.; Ueda, I. Chem. Pharm. Bull., 1991, 39, 3331-3334; Miller, A. E.; Feeney, D. J.; Ma, Y.; Zarcone, L.; Aziz, M. A.; Magnuson, E. Synth. Commun., 1990, 20, 217-226; Atherton, F. R.; Lambert, R. W. Tetrahedron. 1983, 39, 2599-2608; Ding, Y. X.; Weber, W. P., Synthesis, 1987, 823-824; Mironova, D. F.; Staninets, V. I. Ukr. Khim. Zh., 1986, 52, 1269-1273; Zbiral, E.; Schoerkhuber, W. Liebigs Ann. Chem., 1982, 1870-1890; Tsuge, O.; Urano, S.; Oe, K. J. Org Chem., 1980, 45, 5130-5136; Yamamoto, I.; Tokanou, H.; Uemura, H.; Gotoh, H. J. Chem. Soc., Perkin Trans. 1, 1977, 1241-1243; Imhof, R.; Ladner, D. W.; Muchowski, J. M. J. Org Chem., 1977, 42, 3709-3713; Viehe, H. G.; George, P. Chimia, 1975, 29, 209-210; Kauer, J. C.; Sheppard, W. A. J. Org. Chem., 1967, 32, 3580-3593.
8. Ishii, K.; Hatanaka, M.; Ueda, I. Chem. Pharm. Bull., 1991, 39, 3331-3334; Miller, A. E.; Feeney, D. J.; Ma, Y.; Zarcone, L.; Aziz, M. A.; Magnuson, E. Synth. Commun., 1990, 20, 217-226; Atherton, F. R.; Lambert, R. W. Tetrahedron. 1983, 39, 2599-2608; Ding, Y. X.; Weber, W. P., Synthesis, 1987, 823-824; Mironova, D. F.; Staninets, V. I. Ukr. Khim. Zh., 1986, 52, 1269-1273; Zbiral, E.; Schoerkhuber, W. Liebigs Ann. Chem., 1982, 1870-1890; Tsuge, O.; Urano, S.; Oe, K. J. Org Chem., 1980, 45, 5130-5136; Yamamoto, I.; Tokanou, H.; Uemura, H.; Gotoh, H. J. Chem. Soc., Perkin Trans. 1, 1977, 1241-1243; Imhof, R.; Ladner, D. W.; Muchowski, J. M. J. Org Chem., 1977, 42, 3709-3713; Viehe, H. G.; George, P. Chimia, 1975, 29, 209-210; Kauer, J. C.; Sheppard, W. A. J. Org. Chem., 1967, 32, 3580-3593.
9. Ishii, K.; Hatanaka, M.; Ueda, I. Chem. Pharm. Bull., 1991, 39, 3331-3334; Miller, A. E.; Feeney, D. J.; Ma, Y.; Zarcone, L.; Aziz, M. A.; Magnuson, E. Synth. Commun., 1990, 20, 217-226; Atherton, F. R.; Lambert, R. W. Tetrahedron. 1983, 39, 2599-2608; Ding, Y. X.; Weber, W. P., Synthesis, 1987, 823-824; Mironova, D. F.; Staninets, V. I. Ukr. Khim. Zh., 1986, 52, 1269-1273; Zbiral, E.; Schoerkhuber, W. Liebigs Ann. Chem., 1982, 1870-1890; Tsuge, O.; Urano, S.; Oe, K. J. Org Chem., 1980, 45, 5130-5136; Yamamoto, I.; Tokanou, H.; Uemura, H.; Gotoh, H. J. Chem. Soc., Perkin Trans. 1, 1977, 1241-1243; Imhof, R.; Ladner, D. W.; Muchowski, J. M. J. Org Chem., 1977, 42, 3709-3713; Viehe, H. G.; George, P. Chimia, 1975, 29, 209-210; Kauer, J. C.; Sheppard, W. A. J. Org. Chem., 1967, 32, 3580-3593.
10. Ishii, K.; Hatanaka, M.; Ueda, I. Chem. Pharm. Bull., 1991, 39, 3331-3334; Miller, A. E.; Feeney, D. J.; Ma, Y.; Zarcone, L.; Aziz, M. A.; Magnuson, E. Synth. Commun., 1990, 20, 217-226; Atherton, F. R.; Lambert, R. W. Tetrahedron. 1983, 39, 2599-2608; Ding, Y. X.; Weber, W. P., Synthesis, 1987, 823-824; Mironova, D. F.; Staninets, V. I. Ukr. Khim. Zh., 1986, 52, 1269-1273; Zbiral, E.; Schoerkhuber, W. Liebigs Ann. Chem., 1982, 1870-1890; Tsuge, O.; Urano, S.; Oe, K. J. Org Chem., 1980, 45, 5130-5136; Yamamoto, I.; Tokanou, H.; Uemura, H.; Gotoh, H. J. Chem. Soc., Perkin Trans. 1, 1977, 1241-1243; Imhof, R.; Ladner, D. W.; Muchowski, J. M. J. Org Chem., 1977, 42, 3709-3713; Viehe, H. G.; George, P. Chimia, 1975, 29, 209-210; Kauer, J. C.; Sheppard, W. A. J. Org. Chem., 1967, 32, 3580-3593.
11. Ishii, K.; Hatanaka, M.; Ueda, I. Chem. Pharm. Bull., 1991, 39, 3331-3334; Miller, A. E.; Feeney, D. J.; Ma, Y.; Zarcone, L.; Aziz, M. A.; Magnuson, E. Synth. Commun., 1990, 20, 217-226; Atherton, F. R.; Lambert, R. W. Tetrahedron. 1983, 39, 2599-2608; Ding, Y. X.; Weber, W. P., Synthesis, 1987, 823-824; Mironova, D. F.; Staninets, V. I. Ukr. Khim. Zh., 1986, 52, 1269-1273; Zbiral, E.; Schoerkhuber, W. Liebigs Ann. Chem., 1982, 1870-1890; Tsuge, O.; Urano, S.; Oe, K. J. Org Chem., 1980, 45, 5130-5136; Yamamoto, I.; Tokanou, H.; Uemura, H.; Gotoh, H. J. Chem. Soc., Perkin Trans. 1, 1977, 1241-1243; Imhof, R.; Ladner, D. W.; Muchowski, J. M. J. Org Chem., 1977, 42, 3709-3713; Viehe, H. G.; George, P. Chimia, 1975, 29, 209-210; Kauer, J. C.; Sheppard, W. A. J. Org. Chem., 1967, 32, 3580-3593.
12. Ishii, K.; Hatanaka, M.; Ueda, I. Chem. Pharm. Bull., 1991, 39, 3331-3334; Miller, A. E.; Feeney, D. J.; Ma, Y.; Zarcone, L.; Aziz, M. A.; Magnuson, E. Synth. Commun., 1990, 20, 217-226; Atherton, F. R.; Lambert, R. W. Tetrahedron. 1983, 39, 2599-2608; Ding, Y. X.; Weber, W. P., Synthesis, 1987, 823-824; Mironova, D. F.; Staninets, V. I. Ukr. Khim. Zh., 1986, 52, 1269-1273; Zbiral, E.; Schoerkhuber, W. Liebigs Ann. Chem., 1982, 1870-1890; Tsuge, O.; Urano, S.; Oe, K. J. Org Chem., 1980, 45, 5130-5136; Yamamoto, I.; Tokanou, H.; Uemura, H.; Gotoh, H. J. Chem. Soc., Perkin Trans. 1, 1977, 1241-1243; Imhof, R.; Ladner, D. W.; Muchowski, J. M. J. Org Chem., 1977, 42, 3709-3713; Viehe, H. G.; George, P. Chimia, 1975, 29, 209-210; Kauer, J. C.; Sheppard, W. A. J. Org. Chem., 1967, 32, 3580-3593.
13. Ishii, K.; Hatanaka, M.; Ueda, I. Chem. Pharm. Bull., 1991, 39, 3331-3334; Miller, A. E.; Feeney, D. J.; Ma, Y.; Zarcone, L.; Aziz, M. A.; Magnuson, E. Synth. Commun., 1990, 20, 217-226; Atherton, F. R.; Lambert, R. W. Tetrahedron. 1983, 39, 2599-2608; Ding, Y. X.; Weber, W. P., Synthesis, 1987, 823-824; Mironova, D. F.; Staninets, V. I. Ukr. Khim. Zh., 1986, 52, 1269-1273; Zbiral, E.; Schoerkhuber, W. Liebigs Ann. Chem., 1982, 1870-1890; Tsuge, O.; Urano, S.; Oe, K. J. Org Chem., 1980, 45, 5130-5136; Yamamoto, I.; Tokanou, H.; Uemura, H.; Gotoh, H. J. Chem. Soc., Perkin Trans. 1, 1977, 1241-1243; Imhof, R.; Ladner, D. W.; Muchowski, J. M. J. Org Chem., 1977, 42, 3709-3713; Viehe, H. G.; George, P. Chimia, 1975, 29, 209-210; Kauer, J. C.; Sheppard, W. A. J. Org. Chem., 1967, 32, 3580-3593.
14. Garbrecht, W. L.; Herbst, R. M. J. Org. Chem., 1953, 18, 1014-1021.
15. Raap, R. Can J. Chem., 1971, 49, 2139-2142; Grimmett, M. R.; Iddon, B. Heterocycles, 1995, 41, 1525-1574; Satoh, Y.; Marcopulos, N. Tetrahedron Lett., 1995, 36, 1759-1762.
16. Raap, R. Can J. Chem., 1971, 49, 2139-2142; Grimmett, M. R.; Iddon, B. Heterocycles, 1995, 41, 1525-1574; Satoh, Y.; Marcopulos, N. Tetrahedron Lett., 1995, 36, 1759-1762.
17. Raap, R. Can J. Chem., 1971, 49, 2139-2142; Grimmett, M. R.; Iddon, B. Heterocycles, 1995, 41, 1525-1574; Satoh, Y.; Marcopulos, N. Tetrahedron Lett., 1995, 36, 1759-1762.
18. Addition of sodium azide to the nitrile of the cyanoamide forms a guanidinium azide species which can exist in two tautomeric forms and undergoes electrocyclic cyclisation to give the 1-aryl-5-aminotetrazole product in preference to the 5-anilinotetrazole product. See Satoh, Y.; Marcopulos, N. Tetrahedron Lett. 1995, 36, 1759-1762 for a full discussion.
19. Armour, D. R.; Chung, K. M.; Congreve, M. S.; Evans, B.; Guntrip, S.; Hubbard, T.; Kay C.; Middlemiss, D.; Mordaunt J. E.; Pegg, N. A.; Vinader, M. V.; Ward, P.; Watson, S. P. Bioorganic Med. Chem. Lett. 1996, in preparation. The preparation of a protected version of this compound can be found in; Desai, M. C.; Lefkowitz, S. L.; Thadeio, P. F.; Longo, K. P.; Snider, M. R. J. Med. Chem., 1992, 35, 4911-13.
20. Armour, D. R.; Chung, K. M.; Congreve, M. S.; Evans, B.; Guntrip, S.; Hubbard, T.; Kay C.; Middlemiss, D.; Mordaunt J. E.; Pegg, N. A.; Vinader, M. V.; Ward, P.; Watson, S. P. Bioorganic Med. Chem. Lett. 1996, in preparation. The preparation of a protected version of this compound can be found in; Desai, M. C.; Lefkowitz, S. L.; Thadeio, P. F.; Longo, K. P.; Snider, M. R. J. Med. Chem., 1992, 35, 4911-13.
21. 3 requires 264.1096).
22. Products were single regioisomers and alkyl signals were coincident indicating di-alkylation on the exocyclic nitrogen atom. Under different conditions (methyl iodide, potassium carbonate, dimethylformamide) a mixture of mono-alkylated regioisomers were isolated, suggesting alkylation of the ring.