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P. Ducray et al. / Bioorg. Med. Chem. Lett. 18 (2008) 2935–2938
the upper part of midgut. Iodine fixed worms were
counted after destaining. Efficacy is expressed in percent
reduction of worm numbers compared to the geometric
mean number of worms collected from the control group,
using Abbot’s formula.
favorable tolerability of this class of compounds ob-
served in ruminants can be confirmed for humans, hu-
man medical practice may also benefit from this new
alternative to current treatments.
10. Synthesis of amino-acetonitriles 1–20 and 25–33, typical
procedures5: data for compound 19: mp = 102–103 °C. 1H
NMR (CDCl3, 400 MHz): d 7.80 (d, J = 8.8 Hz, 2H),
7.47–7.41 (m, 1H), 7.29–7.25 (m, 2H), 6.90 (dd, J = 11.0,
6.2 Hz, 1H), 6.54 (br s, 1H), 4.59 (d, J = 9.0 Hz, 1H), 4.37
(d, J = 9.0 Hz, 1H), 1.96 (s, 3H). HRMS (m/z): [M+H]+
calcd for C19H12F8N2O3, 469.0793; found, 469.0793.
11. All compounds listed in Table 1 gave satisfactory 1H
NMR data and purity.
Acknowledgments
The authors are grateful to M. Keller, C. Bergamin, C.
Durano, N. Estable, J. Lambert, M. Mueller, S. Mulha-
user, L. Sabato, F. Schroeder, M. Senn, U. Thuering
and A. Zehntner for technical assistance. The authors
thank B. Hosking, A. Redpath and R. Steiger for review
of this manuscript.
12. Gauvry, N.; Goebel, T.; Ducray, P.; Pautrat, F.; Kamin-
sky, R.; Jung, M. WO 05/044784, 2005; Chem. Abstr. 2005,
142, 481750.
13. Synthesis of amino-acetonitriles 21–24 and 34–36, typical
References and notes
1
procedures12: data for compound 36: mp = 69–73 °C. H
NMR (CDCl3, 400 MHz) d 7.81 (m, 2H), 7.76–7.72 (m,
3H), 7.41 (d, J = 8.1 Hz, 1H), 7.30 (s, 1H), 6.50 (br s, 1H),
4.71 (d, J = 8.9 Hz, 1H), 4.50 (d, J = 8.9 Hz, 1H), 2.00 (s,
3H). HRMS (m/z): [M+H]+ calcd for C20H13F6N3O2S,
474.0754; found, 474.0754.
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