Synthesis of novel proline and γ-lactam derivatives as non-peptide mimics of Somatostatin/Sandostatin®

Tetrahedron

Volumn 55, Issue 33, 1999, Pages 10135-10154

  Damour, Dominique ^a   Herman, Frédéric ^a   Labaudinière, Richard ^a   Pantel, Guy ^a   Vuilhorgne, Marc ^a   Mignani, Serge ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA LACTAM DERIVATIVE; OCTREOTIDE; PROLINE DERIVATIVE; SOMATOSTATIN;

ARTICLE; DIASTEREOISOMER; DRUG STRUCTURE; MOLECULAR MIMICRY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0033551723     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00561-X     Document Type: Article

References (39)

1. a) Damour, D.; Barreau, M.; Blanchard, J-C.; Burgevin, M-C.; Doble, A.; Herman, F.; Pantel, G.; James-Surcouf, E.; Vuilhorgne, M.; Mignani, S., Poitou, L., Le Merrer, Y., Depezay, J-C. Bioorg. Med. Chem. Lett., 1996, 6, 1667. b) Damour, D. ; Barreau, M. ; Blanchard, J.-C. ; Burgevin, M.-C. ; Doble, A. ; Pantel, G. ; Labaudiniere, R. ; Mignani, S. Chem. Lett. 1998, 943.
2. a) Damour, D.; Barreau, M.; Blanchard, J-C.; Burgevin, M-C.; Doble, A.; Herman, F.; Pantel, G.; James-Surcouf, E.; Vuilhorgne, M.; Mignani, S., Poitou, L., Le Merrer, Y., Depezay, J-C. Bioorg. Med. Chem.lett., 1996, 6, 1667. b) Damour, D. ; Barreau, M. ; Blanchard, J.-C. ; Burgevin, M.-C. ; Doble, A. ; Pantel, G. ; Labaudiniere, R. ; Mignani, S. Chem. Lett. 1998, 943.
3. Schally, A. V.; Coy, D. H.; Meyers, C. A. Ann. Rev. Biochem., 1978, 47, 89.
4. Patel, Y. C. ; Greenwood, M. T. ; Panetta, R. ; Demchyshyn, L. ; Niznik, H. ; Srikant, C. B. Life Sci. 1995, 57, 1249.
5. a) For cyclic-peptides, see: Veber, D. F. ; Holly, F. W. ; Nutt, R. F. ; Bergstrand, S. J. ; Brady, S. F. ; Hirschmann, R. ; Glitzer, M. S.; Saperstein, R. Nature, 1979, 280, 512. Nutt, R. F. ; Veber, D. F. ; Saperstein, R. J. Am. Chem. Soc., 1980, 102, 6539. Veber, D. F. ; Freidinger, R. M., Perlow ; D. S., Strachan, R. G. ; Nutt, R. F. ; Arison, B. H. ; Homnick, C. ; Randall, W. C. ; Saperstein, R. ; Hirschmann, R.Nature, 1981, 292, 55. Elseviers, M. ; Van Der Auwera, L. ; Pepermans, H. ; Tourwé, D. ; Van Binst, G. Biochemical and Research Communication, 1988, 154, 515. Spanevello, R. A. ; Hirschmann, R. ; Raynor, K. ; Reisine, T. ; Nutt, R. F. Tetrahedron Lett., 1991, 32, 4675. Huang, Z. ; He Ya-Bo, H ; Raynor, K. ;Tallent, M. ; Reisine, T. ; Goodman, M.J. Am. Chem. Soc., 1992, 114, 9390.
6. a) For cyclic-peptides, see: Veber, D. F. ; Holly, F. W. ; Nutt, R. F. ; Bergstrand, S. J. ; Brady, S. F. ; Hirschmann, R. ; Glitzer, M. S.; Saperstein, R. Nature, 1979, 280, 512. Nutt, R. F. ; Veber, D. F. ; Saperstein, R. J. Am. Chem. Soc., 1980, 102, 6539. Veber, D. F. ; Freidinger, R. M., Perlow ; D. S., Strachan, R. G. ; Nutt, R. F. ; Arison, B. H. ; Homnick, C. ; Randall, W. C. ; Saperstein, R. ; Hirschmann, R.Nature, 1981, 292, 55. Elseviers, M. ; Van Der Auwera, L. ; Pepermans, H. ; Tourwé, D. ; Van Binst, G. Biochemical and Research Communication, 1988, 154, 515. Spanevello, R. A. ; Hirschmann, R. ; Raynor, K. ; Reisine, T. ; Nutt, R. F. Tetrahedron Lett., 1991, 32, 4675. Huang, Z. ; He Ya-Bo, H ; Raynor, K. ;Tallent, M. ; Reisine, T. ; Goodman, M.J. Am. Chem. Soc., 1992, 114, 9390.
7. a) For cyclic-peptides, see: Veber, D. F. ; Holly, F. W. ; Nutt, R. F. ; Bergstrand, S. J. ; Brady, S. F. ; Hirschmann, R. ; Glitzer, M. S.; Saperstein, R. Nature, 1979, 280, 512. Nutt, R. F. ; Veber, D. F. ; Saperstein, R. J. Am. Chem. Soc., 1980, 102, 6539. Veber, D. F. ; Freidinger, R. M., Perlow ; D. S., Strachan, R. G. ; Nutt, R. F. ; Arison, B. H. ; Homnick, C. ; Randall, W. C. ; Saperstein, R. ; Hirschmann, R. Nature, 1981, 292, 55. Elseviers, M. ; Van Der Auwera, L. ; Pepermans, H. ; Tourwé, D. ; Van Binst, G. Biochemical and Research Communication, 1988, 154, 515. Spanevello, R. A. ; Hirschmann, R. ; Raynor, K. ; Reisine, T. ; Nutt, R. F. Tetrahedron Lett., 1991, 32, 4675. Huang, Z. ; He Ya-Bo, H ; Raynor, K. ;Tallent, M. ; Reisine, T. ; Goodman, M.J. Am. Chem. Soc., 1992, 114, 9390.
8. a) For cyclic-peptides, see: Veber, D. F. ; Holly, F. W. ; Nutt, R. F. ; Bergstrand, S. J. ; Brady, S. F. ; Hirschmann, R. ; Glitzer, M. S.; Saperstein, R. Nature, 1979, 280, 512. Nutt, R. F. ; Veber, D. F. ; Saperstein, R. J. Am. Chem. Soc., 1980, 102, 6539. Veber, D. F. ; Freidinger, R. M., Perlow ; D. S., Strachan, R. G. ; Nutt, R. F. ; Arison, B. H. ; Homnick, C. ; Randall, W. C. ; Saperstein, R. ; Hirschmann, R. Nature, 1981, 292, 55. Elseviers, M. ; Van Der Auwera, L. ; Pepermans, H. ; Tourwé, D. ; Van Binst, G. Biochemical and Research Communication, 1988, 154, 515. Spanevello, R. A. ; Hirschmann, R. ; Raynor, K. ; Reisine, T. ; Nutt, R. F. Tetrahedron Lett., 1991, 32, 4675. Huang, Z. ; He Ya-Bo, H ; Raynor, K. ;Tallent, M. ; Reisine, T. ; Goodman, M.J. Am. Chem. Soc., 1992, 114, 9390.
9. a) For cyclic-peptides, see: Veber, D. F. ; Holly, F. W. ; Nutt, R. F. ; Bergstrand, S. J. ; Brady, S. F. ; Hirschmann, R. ; Glitzer, M. S.; Saperstein, R. Nature, 1979, 280, 512. Nutt, R. F. ; Veber, D. F. ;Saperstein, R. J. Am. Chem. Soc., 1980, 102, 6539. Veber, D. F. ; Freidinger, R. M., Perlow ; D. S., Strachan, R. G. ; Nutt, R. F. ; Arison, B. H. ; Homnick, C. ; Randall, W. C. ; Saperstein, R. ; Hirschmann, R. Nature, 1981, 292, 55. Elseviers, M. ; Van Der Auwera, L. ; Pepermans, H. ; Tourwé, D. ; Van Binst, G. Biochemical and Research Communication, 1988, 154, 515. Spanevello, R. A. ; Hirschmann, R. ; Raynor, K. ; Reisine, T. ; Nutt, R. F. Tetrahedron Lett., 1991, 32, 4675. Huang, Z. ; He Ya-Bo, H ; Raynor, K. ;Tallent, M. ; Reisine, T. ; Goodman, M.J. Am. Chem. Soc., 1992, 114, 9390.
10. a) For cyclic-peptides, see: Veber, D. F. ; Holly, F. W. ; Nutt, R. F. ; Bergstrand, S. J. ; Brady, S. F. ; Hirschmann, R. ; Glitzer, M. S.; Saperstein, R. Nature, 1979, 280, 512. Nutt, R. F. ; Veber, D. F. ; Saperstein, R. J. Am. Chem. Soc., 1980, 102, 6539. Veber, D. F. ; Freidinger, R. M., Perlow ; D. S., Strachan, R. G. ; Nutt, R. F. ; Arison, B. H. ; Homnick, C. ; Randall, W. C. ; Saperstein, R. ; Hirschmann, R. Nature, 1981, 292, 55. Elseviers, M. ; Van Der Auwera, L. ; Pepermans, H. ; Tourwé, D. ; Van Binst, G. Biochemical and Research Communication, 1988, 154, 515. Spanevello, R. A. ; Hirschmann, R. ; Raynor, K. ; Reisine, T. ; Nutt, R. F. Tetrahedron Lett., 1991, 32, 4675. Huang, Z. ; He Ya-Bo, H ; Raynor, K. ; Tallent, M. ; Reisine, T. ; Goodman, M.J. Am. Chem. Soc., 1992, 114, 9390.
11. b) For non-peptide mimics, see: original work was performed by Merck Research Laboratories [(a) Nicolaou, K. C. ; Salvino, J. M. ; Raynor, K. ; Pietranico, S. ; Reisine, T. ; Freidinger, R.M. ; Hirschmann, R. Peptides-Chemistry Structure and Biology: Proceedings of The Eleventh American Peptide Symposium. Rivier, J. E. ; Marshall, G. R. Eds; ESCOM, Leiden, 1990, 881. (b) Hirschmann, R. ; Nicolaou, K. C. ; Pietranico, A. ; Salvino, J. ; Leahy, E. M. ; Sprengeler, P. A. ; Furst, G. ; Smith, B. ; Strader, C. D. ; Cascieri, A. ; Candelore, M. R. ; Donaldson, C. ; Vale, W. ; Maechler, L. J. Am. Chem. Soc., 1992, 114, 9217. (c) Hirschmann, R. ; Nicolaou, K. C. ; Pietranico, S. ; Leahy, E. M. ; Salvino, J. ; Arison, B. ; Cichy, M. A. ; Spoors, P. G. ; Shakespeare, W. C. ; Sprengeler, P. A. ; Hamley, P. ; Smith, A. B. ; Reisine, T. ; Raynor, K. ; Maechler, L. ; Donaldson, C. ; Vale, W. ; Freidinger, R. M. ; Cascieri, M. R. ; Strader, C.D. J. Am. Chem. Soc., 1993, 115, 12550] and other examples were published by Sandoz Pharma Research Laboratories [(d) Papageorgiou, C. ; Haltiner, R. ; Bruns C. ; Petcher, T. Bioorg. Med. Chem. Lett., 1992, 2, 135. (e) Papageorgiou, C. ; Borer, X. Bioorg. Med. Chem. Lett., 1996, 6, 267. (f) Goodman, M. ; Zhang, J. Chemtracts-Organic Chemistry, 1997, 10, 629.
12. b) For non-peptide mimics, see: original work was performed by Merck Research Laboratories [(a)Nicolaou, K. C. ; Salvino, J. M. ; Raynor, K. ; Pietranico, S. ; Reisine, T. ; Freidinger, R.M. ; Hirschmann, R. Peptides-Chemistry Structure and Biology: Proceedings of The Eleventh American Peptide Symposium. Rivier, J. E. ; Marshall, G. R. Eds; ESCOM, Leiden, 1990, 881. (b) Hirschmann, R. ; Nicolaou, K. C. ; Pietranico, A. ; Salvino, J. ; Leahy, E. M. ; Sprengeler, P. A. ; Furst, G. ; Smith, B. ; Strader, C. D. ; Cascieri, A. ; Candelore, M. R. ; Donaldson, C. ; Vale, W. ; Maechler, L. J. Am. Chem. Soc., 1992, 114, 9217. (c) Hirschmann, R. ; Nicolaou, K. C. ; Pietranico, S. ; Leahy, E. M. ; Salvino, J. ; Arison, B. ; Cichy, M. A. ; Spoors, P. G. ; Shakespeare, W. C. ; Sprengeler, P. A. ; Hamley, P. ; Smith, A. B. ; Reisine, T. ; Raynor, K. ; Maechler, L. ; Donaldson, C. ; Vale, W. ; Freidinger, R. M. ; Cascieri, M. R. ; Strader, C.D. J. Am. Chem. Soc., 1993, 115, 12550] and other examples were published by Sandoz Pharma Research Laboratories [(d) Papageorgiou, C. ; Haltiner, R. ; Bruns C. ; Petcher, T. Bioorg. Med. Chem. Lett., 1992, 2, 135. (e) Papageorgiou, C. ; Borer, X. Bioorg. Med. Chem. Lett., 1996, 6, 267. (f) Goodman, M. ; Zhang, J. Chemtracts-Organic Chemistry, 1997, 10, 629.
13. b) For non-peptide mimics, see: original work was performed by Merck Research Laboratories [(a)Nicolaou, K. C. ; Salvino, J. M. ; Raynor, K. ; Pietranico, S. ; Reisine, T. ; Freidinger, R.M. ; Hirschmann, R. Peptides-Chemistry Structure and Biology: Proceedings of The Eleventh American Peptide Symposium. Rivier, J. E. ; Marshall, G. R. Eds; ESCOM, Leiden, 1990, 881. (b) Hirschmann, R. ; Nicolaou, K. C. ; Pietranico, A. ; Salvino, J. ; Leahy, E. M. ; Sprengeler, P. A. ; Furst, G. ; Smith, B. ; Strader, C. D. ; Cascieri, A. ; Candelore, M. R. ; Donaldson, C. ; Vale, W. ; Maechler, L. J. Am. Chem. Soc., 1992, 114, 9217. (c) Hirschmann, R. ; Nicolaou, K. C. ; Pietranico, S. ; Leahy, E. M. ; Salvino, J. ; Arison, B. ; Cichy, M. A. ; Spoors, P. G. ; Shakespeare, W. C. ; Sprengeler, P. A. ; Hamley, P. ; Smith, A. B. ; Reisine, T. ; Raynor, K. ; Maechler, L. ; Donaldson, C. ; Vale, W. ; Freidinger, R. M. ; Cascieri, M. R. ; Strader, C.D. J. Am. Chem. Soc., 1993, 115, 12550] and other examples were published by Sandoz Pharma Research Laboratories [(d) Papageorgiou, C. ; Haltiner, R. ; Bruns C. ; Petcher, T. Bioorg. Med. Chem. Lett., 1992, 2, 135. (e) Papageorgiou, C. ; Borer, X. Bioorg. Med. Chem. Lett., 1996, 6, 267. (f) Goodman, M. ; Zhang, J. Chemtracts-Organic Chemistry, 1997, 10, 629.
14. b) For non-peptide mimics, see: original work was performed by Merck Research Laboratories [(a)Nicolaou, K. C. ; Salvino, J. M. ; Raynor, K. ; Pietranico, S. ; Reisine, T. ; Freidinger, R.M. ; Hirschmann, R. Peptides-Chemistry Structure and Biology: Proceedings of The Eleventh American Peptide Symposium. Rivier, J. E. ; Marshall, G. R. Eds; ESCOM, Leiden, 1990, 881. (b) Hirschmann, R. ; Nicolaou, K. C. ;Pietranico, A. ; Salvino, J. ; Leahy, E. M. ; Sprengeler, P. A. ; Furst, G. ; Smith, B. ; Strader, C. D. ;Cascieri, A. ; Candelore, M. R. ; Donaldson, C. ; Vale, W. ; Maechler, L. J. Am. Chem. Soc., 1992, 114, 9217. (c) Hirschmann, R. ; Nicolaou, K. C. ; Pietranico, S. ; Leahy, E. M. ; Salvino, J. ; Arison, B. ; Cichy, M. A. ; Spoors, P. G. ; Shakespeare, W. C. ; Sprengeler, P. A. ; Hamley, P. ; Smith, A. B. ; Reisine, T. ; Raynor, K. ; Maechler, L. ; Donaldson, C. ; Vale, W. ; Freidinger, R. M. ; Cascieri, M. R. ; Strader, C.D. J. Am. Chem. Soc., 1993, 115, 12550] and other examples were published by Sandoz Pharma Research Laboratories [(d) Papageorgiou, C. ; Haltiner, R. ; Bruns C. ; Petcher, T. Bioorg. Med. Chem. Lett., 1992, 2, 135. (e) Papageorgiou, C. ; Borer, X. Bioorg. Med. Chem. Lett., 1996, 6, 267. (f) Goodman, M. ; Zhang, J. Chemtracts-Organic Chemistry, 1997, 10, 629.
15. b) For non-peptide mimics, see: original work was performed by Merck Research Laboratories [(a)Nicolaou, K. C. ; Salvino, J. M. ; Raynor, K. ; Pietranico, S. ; Reisine, T. ; Freidinger, R.M. ; Hirschmann, R. Peptides-Chemistry Structure and Biology: Proceedings of The Eleventh American Peptide Symposium.Rivier, J. E. ; Marshall, G. R. Eds; ESCOM, Leiden, 1990, 881. (b) Hirschmann, R. ; Nicolaou, K. C. ;Pietranico, A. ; Salvino, J. ; Leahy, E. M. ; Sprengeler, P. A. ; Furst, G. ; Smith, B. ; Strader, C. D. ;Cascieri, A. ; Candelore, M. R. ; Donaldson, C. ; Vale, W. ; Maechler, L. J. Am. Chem. Soc., 1992, 114, 9217. (c) Hirschmann, R. ; Nicolaou, K. C. ; Pietranico, S. ; Leahy, E. M. ; Salvino, J. ; Arison, B. ; Cichy, M. A. ; Spoors, P. G. ; Shakespeare, W. C. ; Sprengeler, P. A. ; Hamley, P. ; Smith, A. B. ; Reisine, T. ; Raynor, K. ; Maechler, L. ; Donaldson, C. ; Vale, W. ; Freidinger, R. M. ; Cascieri, M. R. ; Strader, C.D. J. Am. Chem. Soc., 1993, 115, 12550] and other examples were published by Sandoz Pharma Research Laboratories [(d) Papageorgiou, C. ; Haltiner, R. ; Bruns C. ; Petcher, T. Bioorg. Med. Chem. Lett., 1992, 2, 135. (e) Papageorgiou, C. ; Borer, X. Bioorg. Med. Chem. Lett., 1996, 6, 267. (f) Goodman, M. ; Zhang, J. Chemtracts-Organic Chemistry, 1997, 10, 629.
16. b) For non-peptide mimics, see: original work was performed by Merck Research Laboratories [(a)Nicolaou, K. C. ; Salvino, J. M. ; Raynor, K. ; Pietranico, S. ; Reisine, T. ; Freidinger, R.M. ; Hirschmann, R. Peptides-Chemistry Structure and Biology: Proceedings of The Eleventh American Peptide Symposium. Rivier, J. E. ; Marshall, G. R. Eds; ESCOM, Leiden, 1990, 881. (b) Hirschmann, R. ; Nicolaou, K. C. ;Pietranico, A. ; Salvino, J. ; Leahy, E. M. ; Sprengeler, P. A. ; Furst, G. ; Smith, B. ; Strader, C. D. ;Cascieri, A. ; Candelore, M. R. ; Donaldson, C. ; Vale, W. ; Maechler, L. J. Am. Chem. Soc., 1992, 114, 9217. (c) Hirschmann, R. ; Nicolaou, K. C. ; Pietranico, S. ; Leahy, E. M. ; Salvino, J. ; Arison, B. ; Cichy, M. A. ; Spoors, P. G. ; Shakespeare, W. C. ; Sprengeler, P. A. ; Hamley, P. ; Smith, A. B. ; Reisine, T. ; Raynor, K. ; Maechler, L. ; Donaldson, C. ; Vale, W. ; Freidinger, R. M. ; Cascieri, M. R. ; Strader, C.D. J. Am. Chem. Soc., 1993, 115, 12550] and other examples were published by Sandoz Pharma Research Laboratories [(d) Papageorgiou, C. ; Haltiner, R. ; Bruns C. ; Petcher, T. Bioorg. Med. Chem. Lett., 1992, 2, 135. (e) Papageorgiou, C. ; Borer, X. Bioorg. Med. Chem. Lett., 1996, 6, 267. (f) Goodman, M. ; Zhang, J. Chemtracts-Organic Chemistry, 1997, 10, 629.
17. Bauer, W.; Briner, U.; Doepfiner, W.; Haller, R.; Huguenin, R.; Marbach, P.; Petcher, T. J.; Pless, J. Life Sci., 1982, 31, 1133.
18. The term of ambiscalemic is proposed as a descriptor for enantiomerically substances with unknown absolute configurations and is delineated as shown in Schemes 3-10 (Maehr, H. Chemical & Engineering News, 1991, August 26, 2).
19. a) Introduction of proline moiety is well-known to be an efficient way to introduce conformational restrictions into peptides, and thus was incorporated as conformationally fixed analogues of corresponding aminoacids, for a review, see: Toniolo, C. Int. J. Protein Res., 1990, 35, 287 and references cited therein; and for an example, see: Webb, T. R.; Eigenbrot, C. J. Org. Chem., 1991, 56, 3009 and references cited therein;
20. a) Introduction of proline moiety is well-known to be an efficient way to introduce conformationalrestrictions into peptides, and thus was incorporated as conformationally fixed analogues of correspondingaminoacids, for a review, see: Toniolo, C. Int. J. Protein Res., 1990, 35, 287 and references cited therein; and for an example, see: Webb, T. R.; Eigenbrot, C. J. Org. Chem., 1991, 56, 3009 and references cited therein.
21. b) For examples of utilization of γ-lactam-constrained peptides, see: Freidinger, R. M., J. Org. Chem., 1985, 50, 3631. Wolf, J-P., Rapoport, J. Org. Chem., 1989, 54, 3164. Zydowsky, T. M., Dellaria, J. F., Nellans, H., J. Org. Chem., 1988, 53, 5607.
22. b) For examples of utilization of γ-lactam-constrained peptides, see: Freidinger, R. M., J. Org. Chem., 1985, 50, 3631. Wolf, J-P., Rapoport, J. Org. Chem., 1989, 54, 3164. Zydowsky, T. M., Dellaria, J. F., Nellans, H., J. Org. Chem., 1988, 53, 5607.
23. b) For examples of utilization of γ-lactam-constrained peptides, see: Freidinger, R. M., J. Org. Chem., 1985, 50, 3631. Wolf, J-P., Rapoport, J. Org. Chem., 1989, 54, 3164. Zydowsky, T. M., Dellaria, J. F., Nellans, H., J. Org. Chem., 1988, 53, 5607.
24. The forms A and B represent each corresponding enantiomerically pure diastereoisomer.
25. 3, rt, 12h].
26. Sarges, R.; Tretter, J. R. J. Org. Chem., 1974, 12, 1710. Chung, J., Y., L.; Wasicak, J. T.; Arnold, W., A.; May, C., S.; Nadzan, A., M.; Holladay, M., W. J. Org. Chem., 1990, 55, 270.
27. Sarges, R.; Tretter, J. R. J. Org. Chem., 1974, 12, 1710. Chung, J., Y., L.; Wasicak, J. T.; Arnold, W., A.; May, C., S.; Nadzan, A., M.; Holladay, M., W. J. Org. Chem., 1990, 55, 270.
28. Sakaitani, M.; Ohfune, Y. J. Org. Chem., 1990, 55, 870.
29. Damour, D. ; M. Vuilhorgne, M. ; Pulicani, J-P. ; Mignani, S. Synlett 1999, submitted for publication.
30. Pindur, U.; Pfeufer, L. Monatsh. Chem. 1989, 120, 157.
31. Shono, T.; Terauchi, J. ; Matsumura, Y. Chem. Lett., 1989, 1963 and references cited therein.
32. For other examples of cyclization reaction giving γ-lactams, see: Thaisrivongs, S. WO Patent 87/05909, 1987 (C.A. 87/291632); Barlos, K. ; Papaioannou, D. ; Voliotis, S. Liebigs Ann. Chem., 1988, 12, 1127. Thaisrivongs, S. ; Pals, D. T. ; Turner, S. R. ; Kroll, L. T. J. Med. Chem., 1988, 31, 1369; Yu, K-L.Rajakumar, G. ; Srivastava, L. K. ; Mishra, R. K. ; Johnson, R. L. J. Med. Chem., 1988, 31, 1430. Deal, M.J. ; Hagan, R. M. ; Ireland, S. J. ; Jordan, C. C. ; McElroy, A. B. ; Porter, B. ; Ross, B. C. ; Stephens-Smith, K. M. ; Ward, P. J. Med. Chem., 1992, 35, 4195. Abood, N. A. ; Laneman, S. A. ; Nosal, R., ; Schretzman, L. L. A. US Patent, 5,484,946, 1996 (C.A. 96/087126). Semple, J. E. ; Minami, N. K. ; Tamura, S. Y.;M. Brunck, T. K.; Nutt, R. F. ; Ripka, W. C. Bioorg. & Med. Chem. Lett., 1997, 7, 2421.
33. For other examples of cyclization reaction giving γ-lactams, see: Thaisrivongs, S. WO Patent 87/05909, 1987 (C.A. 87/291632); Barlos, K. ; Papaioannou, D. ; Voliotis, S. Liebigs Ann. Chem., 1988, 12, 1127. Thaisrivongs, S. ; Pals, D. T. ; Turner, S. R. ; Kroll, L. T. J. Med. Chem., 1988, 31, 1369; Yu, K-L.Rajakumar, G. ; Srivastava, L. K. ; Mishra, R. K. ; Johnson, R. L. J. Med. Chem., 1988, 31, 1430. Deal, M.J. ; Hagan, R. M. ; Ireland, S. J. ; Jordan, C. C. ; McElroy, A. B. ; Porter, B. ; Ross, B. C. ; Stephens-Smith, K. M. ; Ward, P. J. Med. Chem., 1992, 35, 4195. Abood, N. A. ; Laneman, S. A. ; Nosal, R., ; Schretzman, L. L. A. US Patent, 5,484,946, 1996 (C.A. 96/087126). Semple, J. E. ; Minami, N. K. ; Tamura, S. Y.;M. Brunck, T. K.; Nutt, R. F. ; Ripka, W. C. Bioorg. & Med. Chem. Lett., 1997, 7, 2421.
34. For other examples of cyclization reaction giving γ-lactams, see: Thaisrivongs, S. WO Patent 87/05909, 1987 (C.A. 87/291632); Barlos, K. ; Papaioannou, D. ; Voliotis, S. Liebigs Ann. Chem., 1988, 12, 1127. Thaisrivongs, S. ; Pals, D. T. ; Turner, S. R. ; Kroll, L. T. J. Med. Chem., 1988, 31, 1369; Yu, K-L.Rajakumar, G. ; Srivastava, L. K. ; Mishra, R. K. ; Johnson, R. L. J. Med. Chem., 1988, 31, 1430. Deal, M.J. ; Hagan, R. M. ; Ireland, S. J. ; Jordan, C. C. ; McElroy, A. B. ; Porter, B. ; Ross, B. C. ; Stephens-Smith, K. M. ; Ward, P. J. Med. Chem., 1992, 35, 4195. Abood, N. A. ; Laneman, S. A. ; Nosal, R., ; Schretzman, L. L. A. US Patent, 5,484,946, 1996 (C.A. 96/087126). Semple, J. E. ; Minami, N. K. ; Tamura, S. Y.;M. Brunck, T. K.; Nutt, R. F. ; Ripka, W. C. Bioorg. & Med. Chem. Lett., 1997, 7, 2421.
35. For other examples of cyclization reaction giving γ-lactams, see: Thaisrivongs, S. WO Patent 87/05909, 1987 (C.A. 87/291632); Barlos, K. ; Papaioannou, D. ; Voliotis, S. Liebigs Ann. Chem., 1988, 12, 1127. Thaisrivongs, S. ; Pals, D. T. ; Turner, S. R. ; Kroll, L. T. J. Med. Chem., 1988, 31, 1369; Yu, K-L. Rajakumar, G. ; Srivastava, L. K. ; Mishra, R. K. ; Johnson, R. L. J. Med. Chem., 1988, 31, 1430. Deal, M.J. ; Hagan, R. M. ; Ireland, S. J. ; Jordan, C. C. ; McElroy, A. B. ; Porter, B. ; Ross, B. C. ; Stephens-Smith, K. M. ; Ward, P. J. Med. Chem., 1992, 35, 4195. Abood, N. A. ; Laneman, S. A. ; Nosal, R., ; Schretzman, L. L. A. US Patent, 5,484,946, 1996 (C.A. 96/087126). Semple, J. E. ; Minami, N. K. ; Tamura, S. Y.;M. Brunck, T. K.; Nutt, R. F. ; Ripka, W. C. Bioorg. & Med. Chem. Lett., 1997, 7, 2421.
36. For other examples of cyclization reaction giving γ-lactams, see: Thaisrivongs, S. WO Patent 87/05909, 1987 (C.A. 87/291632); Barlos, K. ; Papaioannou, D. ; Voliotis, S. Liebigs Ann. Chem., 1988, 12, 1127. Thaisrivongs, S. ; Pals, D. T. ; Turner, S. R. ; Kroll, L. T. J. Med. Chem., 1988, 31, 1369; Yu, K-L.Rajakumar, G. ; Srivastava, L. K. ; Mishra, R. K. ; Johnson, R. L. J. Med. Chem., 1988, 31, 1430. Deal, M. J. ; Hagan, R. M. ; Ireland, S. J. ; Jordan, C. C. ; McElroy, A. B. ; Porter, B. ; Ross, B. C. ; Stephens-Smith, K. M. ; Ward, P. J. Med. Chem., 1992, 35, 4195. Abood, N. A. ; Laneman, S. A. ; Nosal, R., ; Schretzman, L. L. A. US Patent, 5,484,946, 1996 (C.A. 96/087126). Semple, J. E. ; Minami, N. K. ; Tamura, S. Y.;M. Brunck, T. K.; Nutt, R. F. ; Ripka, W. C. Bioorg. & Med. Chem. Lett., 1997, 7, 2421.
37. For other examples of cyclization reaction giving γ-lactams, see: Thaisrivongs, S. WO Patent 87/05909, 1987 (C.A. 87/291632); Barlos, K. ; Papaioannou, D. ; Voliotis, S. Liebigs Ann. Chem., 1988, 12, 1127. Thaisrivongs, S. ; Pals, D. T. ; Turner, S. R. ; Kroll, L. T. J. Med. Chem., 1988, 31, 1369; Yu, K-L.Rajakumar, G. ; Srivastava, L. K. ; Mishra, R. K. ; Johnson, R. L. J. Med. Chem., 1988, 31, 1430. Deal, M.J. ; Hagan, R. M. ; Ireland, S. J. ; Jordan, C. C. ; McElroy, A. B. ; Porter, B. ; Ross, B. C. ; Stephens-Smith, K. M. ; Ward, P. J. Med. Chem., 1992, 35, 4195. Abood, N. A. ; Laneman, S. A. ; Nosal, R., ; Schretzman, L. L. A. US Patent, 5,484,946, 1996 (C.A. 96/087126). Semple, J. E. ; Minami, N. K. ; Tamura, S. Y.;M. Brunck, T. K.; Nutt, R. F. ; Ripka, W. C. Bioorg. & Med. Chem. Lett., 1997, 7, 2421.
38. For other examples of cyclization reaction giving γ-lactams, see: Thaisrivongs, S. WO Patent 87/05909, 1987 (C.A. 87/291632); Barlos, K. ; Papaioannou, D. ; Voliotis, S. Liebigs Ann. Chem., 1988, 12, 1127. Thaisrivongs, S. ; Pals, D. T. ; Turner, S. R. ; Kroll, L. T. J. Med. Chem., 1988, 31, 1369; Yu, K-L.Rajakumar, G. ; Srivastava, L. K. ; Mishra, R. K. ; Johnson, R. L. J. Med. Chem., 1988, 31, 1430. Deal, M.J. ; Hagan, R. M. ; Ireland, S. J. ; Jordan, C. C. ; McElroy, A. B. ; Porter, B. ; Ross, B. C. ; Stephens-Smith, K. M. ; Ward, P. J. Med. Chem., 1992, 35, 4195. Abood, N. A. ; Laneman, S. A. ; Nosal, R., ; Schretzman, L. L. A. US Patent, 5,484,946, 1996 (C.A. 96/087126). Semple, J. E. ; Minami, N. K. ; Tamura, S. Y.; M. Brunck, T. K.; Nutt, R. F. ; Ripka, W. C. Bioorg. & Med. Chem. Lett., 1997, 7, 2421.
39. Srikant, C. B. ; Patel, Y. C. Proc. Natl. Acad. Sci. USA 1981, 78, 3930.