A parallel solution-phase synthesis of substituted 3,7-diazabicyclo[3.3.1] nonanes

Journal of Combinatorial Chemistry

Volumn 6, Issue 5, 2004, Pages 828-834

  Ivachtchenko, Alexander V ^a   Tkachenko, Sergey E ^a   Sandulenko, Yuriy B ^a   Vvedensky, Vladimir Y ^a   Khvat, Alexander V ^a  

^a CHEMDIV INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 (3 CARBOXYPROPYL) 3,7 DIAZABICYCLO[3.3.1]NONANE 3,7 DICARBOXYLIC ACID DI TERT BUTYL ESTER; 2 (4 MORPHOLIN 4 YL 4 OXOBUTYL) 3,7 DIAZABICYCLO[3.3.1]NONANE 3,7 DICARBOXYLIC ACID DI TERT BUTYL ESTER; 2 (4 MORPHOLIN 4 YLBUTYL) 3,7 DIAZABICYCLO[3.3.1]NONANE 3,7 DICARBOXYLIC ACID DI TERT BUTYL ESTER; 4 (3,7 DIAZABICYCLO[3.3.1]NON 2 YL)BUTANOL; 4 (3,7 DIBENZYL 3,7 DIAZABICYCLO[3.3.1]NON 2 YL)BUTANOL; 4 (3,7 DIBENZYL 3,7 DIAZABICYCLO[3.3.1]NON 2 YL)BUTYRIC ACID METHYL ESTER; 4 (7 BENZYL 3,7 DIAZABICYCLO[3.3.1]NON 2 YL)BUTANOL; 4 (7 BENZYL 3,7 DIAZABICYCLO[3.3.1]NON 2 YL)BUTYRIC ACID METHYL ESTER; 4 (7 CYCLOPROPYLMETHYL 3,7 DIAZABICYCLO[3.3.1]NON 3 YL)BUTYRIC ACID METHYL ESTER; 4 (7 ETHYL 3,7 DIAZABICYCLO[3.3.1]NON 2 YL)BUTYRIC ACID METHYL ESTER; 4 (7 METHOXYBENZYL 3,7 DIAZABICYCLO[3.3.1]NON 2 YL)BUTYRIC ACID METHYL ESTER; 4 (7 PHENETYL 3,7 DIAZABICYCLO[3.3.1]NON 2 YL)BUTYRIC ACID METHYL ESTER; 4 [3 BENZYL 7 (4 METHOXYBENZYL) 3,7 DIAZABICYCLO[3.3.1]NON 2 YL]BUTANOL; 4 [3 BENZYL 7 (4 METHOXYBENZYL) 3,7 DIAZABICYCLO[3.3.1]NON 2 YL]BUTYRIC ACID METHYL ESTER; 4 [7 (4 METHOXYBENZYL) 3,7 DIAZABICYCLO[3.3.1]NON 2 YL]BUTANOL; 7 BENZYL 2 (3 METHOXYCARBONYLPROPYL) 3,7 DIAZABICYCLO[3.3.1]NONANE 3 CARBOXYLIC ACID TERT BUTYL ESTER; ALKALI; BICYCLO[3.3.1]NONANE DERIVATIVE; CYTISINE; HETEROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CATALYSIS; COMBINATORIAL LIBRARY; DRUG PURITY; DRUG SYNTHESIS; HYDROGENATION; METHODOLOGY; REACTION ANALYSIS;

EID: 4944234665     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc0499385     Document Type: Article

References (25)

1. Mannich, C.; Mohs, P. Chem. Ber. 1930, 63, 506-512.
2. Wick, E.; Bell, U.; Dengler, H. J. Med. Welt 1971, 22, 303-304.
3. (a) Bosch, R. F.; Milek, I. V.; Popovic, K.; Mermi, J.; Mewis, C.; Kohlkamp, V.; Seipel, L. J. Cardiovasc. Pharmacol. 1999, 33, 762-771.
4. (b) Hahn, K.-J.; Kirchengast, M. EP 0701442, 1996; Chem. Abstr. 1994, 121, 170560s.
5. Schon, U.; Heitmann, W.; Matzel, U. EP 0550383, 1995; Chem. Abstr. 1993, 119, 203392c.
6. Pugsley, M. K.; Goldin, A. L. Eur. J. Pharmacol. 1998, 342, 93-104.
7. (a) Boido, C. C.; Tasso, B.; Boido, V.; Sparatore, F. Farmaco 2003, 58, 265.
8. (b) Slater, Y. E.; Houlihan, L. M.; Maskell, P. D.; Exley, R.; Bermuderz, I.; Lukas, P. J.; Valdivia, A. C.; Cassels, B. K. Neuropharmacology 2003, 44, 503-515.
9. (c) Imming, P.; Klaperski, P.; Stubbs, M. T.; Seitz, G.; Gundisch, D. Eur. J. Med. Chem. 2001, 36, 375-388.
10. (d) O'Neill, B. T. U.S. Patent 6235734, 2001; Chem. Abstr. 1998, 129, 004774k.
11. (e) Marrière, E.; Rouden, J.; Tadino, V.; Lasne, M.-C. Org. Lett. 2000, 2, 1121-1124.
12. (a) Zefirov, N. S.; Palyulin, V. A. Top. Stereochem. 1991, 20, 171-230.
13. (b) Jeyaraman, R.; Avila, S. Chem. Rev. 1981, 81, 149-174.
14. (a) Mannich, C.; Veit, F. Chem. Ber. 1935, 68B, 506-512.
15. (b) Miyahara, Y.; Goto, K.; Inazu, T. Synthesis 2001, 3, 364-366.
16. Bohlmann, F.; Ottawa, N.; Keller, R. Annalen 1954, 587, 162-176.
17. Schön, U.; Antel, J.; Brückner, R.; Messinger, J. J. Med. Chem. 1998, 41, 318-331.
18. Bojadschiewa, M.; Issaev, I.; Totev, I.; Dimov, S. Pharmazie 1971, 26, 643.
19. (a) O'Neill, B. T.; Yohannes, D.; Bundesmann, M. W.; Arnold, E. P. Org. Lett. 2000, 2, 4201-4204.
20. (b) Coe, J. W. Org. Lett. 2000, 2, 4205-4208.
21. (a) Dearden, M. J.; Firkin, C. R.; Hermet, J.-P. R.; O'Brien, P. J. Am. Chem. Soc. 2002, 124, 11870-11871.
22. (b) Primuchamedov, I.; Tillyaev, K. S. Uzbeksky Khim. Zhurn. 1981, 1, 52-55.
23. (c) Primuchamedov, I.; Tillyaev, K. S.; Zaidova, R. A. Uzbeksky Khim. Zhurn. 1982, 3, 63-64.
24. Baru, M.; Ivachtchenko, A. Russian Patent 2,180,609, 2002; Patent PCT WO 02/087740 A1, 2002; Chem. Abstr. 2003, 138, 014907f.
25. For description of this equipment, see: Technology Platform. In Custom Chemistry; Chemical Diversity Labs, Inc.: San Diego, CA, 2002; p 5. Available at http://www.chemdiv.com.