Analgesics, Centrally Acting
Elmar Friderichs
Grünenthal GmbH, Center of Research, Aachen, Germany
Search for more papers by this authorThomas Christoph
Grünenthal GmbH, Center of Research, Aachen, Germany
Search for more papers by this authorHelmut Buschmann
Laboratorios Dr. Esteve S.A., Barcelona, Spain
Search for more papers by this authorElmar Friderichs
Grünenthal GmbH, Center of Research, Aachen, Germany
Search for more papers by this authorThomas Christoph
Grünenthal GmbH, Center of Research, Aachen, Germany
Search for more papers by this authorHelmut Buschmann
Laboratorios Dr. Esteve S.A., Barcelona, Spain
Search for more papers by this authorAbstract
The article contains sections titled:
1. |
Opioids |
1.1. |
Opioids in Clinical Use |
1.1.1. |
Morphine and Morphinane Derivatives |
1.1.2. |
Piperidine Derivatives |
1.1.3. |
Fentanyl and Congeners |
1.1.4. |
Methadone and Congeners |
1.2. |
Other Structures |
1.2.1. |
Mixed Opioid Agonist-Antagonists and Partial Agonists |
1.2.2. |
Opioid Antagonists |
2. |
Anti-Neuropathic Analgesics and Other Nonopioid Compounds |
2.1. |
Neuropathic Pain Treatment |
2.2. |
Individual Compounds |
Specific References
- 1 K. L. Pierce et al., TIPS 16 (1995) 253–256.
- 2 A. Kleemann, J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances, Synthesis, Patents, Applications, Thieme, Stuttgart – New York, 1999 (available in print and CD-ROM).
- 3 For alternative synthesis: US 3 992 495, (Merck & Co.).
- 4 P. Moser et al., J. Med. Chem. 33 (1990) 2358–2368. Link
- 5 Byk Gulden, US 4 4 325 962, 1982; DE 1 946 370, 1969.
- 6 G. L. Plosker, A. J. Wagstaff, Drugs 50 (1995) 1050–1075.
- 7 D. Loew et al., Z. Rheumatol. 44 (1985) 186–192.
- 8 M. Therien et al., Synthesis (2001) 1778–1779.
- 9
A. F. Casy,
R. T. Parfitt:
Opioid Analgesics, Chemistry and Receptors,
Plenum Press,
New York
1986.
10.1007/978-1-4899-0585-7 Google Scholar
- 10
A. F. Casy,
R. T. Parfitt,
Opioid Analgesics. Chemistry and Receptors,
Plenum Press,
New York -London
1986.
10.1007/978-1-4899-0585-7 Google Scholar
- 11 H. Akil et al. Annu. Rev. Neurosci. 7 (1984) 223–255.
- 12 A. Mansour et al., Trends Neurosci. 18 (1995) 22–29.
- 13 A. Herz J. Neural. Transm. Suppl. 18 (1983) 227–233.
- 14 G. B. Stefano, et al. Crit. Rev. Immunol. 16 (1996) 109–144.
- 15 C. Stein et al.,in C. Stein (ed.): Opioids in Pain Control. Basic and Clinical Aspects, Cambridge University Press, Cambridge 1999, pp. 96–108.
- 16 W.R. Martin et al., J. Pharmacol. Exp Ther. 197 (1976) 517–5132.
- 17 C. J. Fowler G. L. Fraser Neurochem. Int. 24 (1994) 401–426.
- 18 W. R. Martin, Pharmacol. Rev. 35 (1983) 283–323.
- 19 B. N. Dhawan et al., Pharmacol Rev. 48 (1996) 567–592.
- 20 J. C. Meunier et al., Nature 377 (1995) 532–535.
- 21 P. L. Wood, Neuropharmacology 21 (1982) 487–497.
- 22 G. W. Pasternak, P. J. Wood, Life Sci. 38 (1986) 1889–1898.
- 23 G. Gaveriaux-Ruff, B. Kieffer, in C. Stein, (ed.): Opioids in Pain Control. Basic and Clinical Aspects, Cambridge University Press, Cambridge 1999, pp. 1–20.
- 24 B. L. Kieffer et al., Proc. Natl. Acad. Sci. U S A. 89 (1992) 12048–12052.
- 25 C. J. Evans et al., Science, 258 (1992) 1952–1955.
- 26 R. K. Reinscheid et al. Science, 270 (1995) 792–794.
- 27 G. Calo' et al. Peptides, 21 (2000) 935–947.
- 28 R. J. Knapp et al., FASEB J. 9 (1995) 516–525.
- 29 S. R. Childers Life Sci. 48 (1991) 1991–2003.
- 30 I. McFadzean, Neuropeptides 11 (1988) 173–180.
- 31 W. F. Simonds, Endocr. Rev. 9 (1988) 200–212.
- 32 A. D. Blake et al. Channels 5 (1997) 231–235.
- 33 P. Y. Law, H. H. Loh, J. Pharmacol. Exp. Ther. 289 (1999) 607–624.
- 34 N. I. Cherny, Drugs 51 (1996) 713–737.
- 35 H. W. Matthes et al., Nature 383 (1996) 819–823.
- 36 B. L. Kieffer, Trends Pharmacol. Sci. 20 (1999) 19–26.
- 37 D. I. Scopes, Drug of the Future 18 (1993) 933–947.
- 38
A. Barber,
R. Gottschlich,
Exp. Opin. Invest. Drugs
6
(1997)
1354–1368.
10.1517/13543784.6.10.1351 Google Scholar
- 39 G. Dondio et al., Exp. Opin. Ther. Patents 7 (1997) 1075–1098.
- 40 M. A. Scheideler, Curr. Opin. CPNS Invest Drugs 2 (2000) 171–177.
- 41 C. Mollereau, L. Mouledous, Peptides. 21 (2000) 907–917.
- 42 R. Bertorelli et al., Trends Pharmacol. Sci. 21 (2000) 233–234.
- 43 A. Mansour et al., Trends Neurosci. 18 (1995) 22–29.
- 44 J. Lipp, Clin. Neuropharmacol. 14 (1991) 131–147.
- 45 T. L Yaksh, Acta Anaesthesiol. Scand. 41 (1997) 94–111.
- 46 C. Stein, Opioids in Pain Control. Basic and Clinical Aspects, Cambridge University Press, Cambridge 1999.
- 47 C. P. Watson, Clin. J. Pain, 16 (2 Suppl.) (2000) S49–55.
- 48 R. C. Etches et al., Can. J. Anaesth. 36 (1989) 165–185.
- 49 J. E. Shook et al., Am. Rev. Respir. Dis. 142 (1990) 895–909.
- 50 M. F. Mulroy, Reg. Anesth. 21 (6 Suppl.) (1996) 89–93.
- 51 F. W. Jackson, Gastroenterology 106 (1994) 820–821.
- 52 T. A. Bowdle, Drug Saf. 19 (1998) 173–189.
- 53 W. Kromer, Dig. Dis. 8 (1990) 361–373.
- 54 I. Mancini, E. Bruera, Support Care Cancer 6 (1998) 356–364.
- 55 A. De Luca, I. M. Coupar, Pharmacol. Ther. 69 (1996) 103–115.
- 56 R. C. Heel et al. Drugs. 15 (1978) 33–52.
- 57 E. Campora et al., J. Pain Symptom Manage. 6 (1991) 428–430.
- 58 R. Aparasu et al., J. Pain Symptom Manage. 18 (1999) 280–288.
- 59 J. P. Blancquaert et al. Eur. J. Pharmacol. 128 (1986) 143–150.
- 60 N. M. Barnes et al., Neuropharmacology 30 (1991) 1073–1083.
- 61 A. Pfeiffer et al., Science 233 (1986) 774–776.
- 62 R. Brown, R. Lo, Aust. N. Z. .J Ment. Health Nurs. 9 (2000) 65–74.
- 63 D. A. Taylor, W. W. Fleming, Pharmacol. Exp. Ther. 297 (2001) 11–18.
- 64 H. A. Heit, Eur. J. Pain 5 Suppl A (2001) 27–29.
- 65 R. F. Reder, Eur. J. Pain. 5 Suppl A (2001) 109–111.
- 66 Knoll, DOS 2 726 925, 1977.
- 67 T. Hudlicky et al.: A historical perspective of morphine synthesis, in: Atta-ur-Rahman (ed.): Studies in Natural products Chemistry, Elsevier, Amsterdam 1996, pp. 43–116.
- 68 D. Trauner et al., Synthesis 1983 203–204.
- 69 J. Mulzer, D. Trauner, Chirality 11 (1999) 475–482.
- 70 J. Frackenpohl, Chem. u. Zeit 34 (2000) 99–112.
- 71
G. J. Meuzelaar et al.,
Eur. J. Org. Chem.
(1999)
2315–2321.
10.1002/(SICI)1099-0690(199909)1999:9<2315::AID-EJOC2315>3.0.CO;2-V CAS Web of Science® Google Scholar
- 72 J. Mulzer, D. Trauner, Chirality 11 (1999) 475–482.
- 73 H. Nagata, et al. Chem. Commun. (2001) 1094–1095.
- 74 H. J. McQuay, B. J. Anaest. 63 (1989) 213–226.
- 75 L L. Christrup, Acta Anaesthesiol. Scand. 41 (1997) 116–122.
- 76 R. Osborne et al., Clin. Pharmacol. Ther. 47 (1990) 12–19.
- 77 J. Lotsch, G. Geisslinger, Clin. Pharmacokinet. 40 (2001) 485–499.
- 78 G. Ehrhart, H. Ruschig: Arzneimittel, Entwicklung, Wirkung, Darstellung, vol. 1, Verlag Chemie, Weinheim 1972, pp. 117–118.
- 79 Boehringer, DRP 247 180, 1912.
- 80 F. J. Muhtadi, M. M. A. Hassan, Anal. Profiles Drug Subs. 10 (1981) 93–138.
- 81 Q. Y. Yue et al., Ther. Drug Monit. 19 (1997) 539–542.
- 82 G. Ehrhart, H. Ruschig: Arzneimittel, Entwicklung, Wirkung, Darstellung, vol. 1, Verlag Chemie, Weinheim 1972, 118.
- 83 E. Merck AG, DRP 131 980, 1902.
- 84 E. Tani et al., Arzneimittelforschung 39 (1989) 1399–1402.
- 85 V. Ozdemir et al., Pharmacogenetics 10 (2000) 373–388.
- 86 G. Ehrhart, H. Ruschig: Arzneimittel, Entwicklung, Wirkung, Darstellung, vol. 1, Verlag Chemie, Weinheim 1972, pp. 79, 115.
- 87 C.E. Inturrisi et al., Life Sci. 33 Suppl 1 (1983) 773–776.
- 88 J. G. Umans, C. E. Inturrisi, J. Pharmacol. Exp. Ther. 218 (1981) 409–415.
- 89 D. K. Wyatt, L. T. Grady, Anal. Profiles Drug Subst. 10 (1981) 357–403.
- 90 U. Boerner et al., Drug Metab. Rev. 4 (1975) 39–73.
- 91 C. E. Inturrisi et al., N. Engl. J. Med. 310 (1984) 1213–1217.
- 92 G. Ehrhart, H. Ruschig: Arzneimittel, Entwicklung, Wirkung, Darstellung, vol. 1, Verlag Chemie, Weinheim 1972, p. 180.
- 93 A. Stein, Pharmazie 10 (1955) 180–186.
- 94 J. E. Edwards et al. Cochrane Database Syst. Rev. (2000) CD 2760.
- 95 H. Matthys et al., Schweiz. Med. Wochenschr. 115 (1985) 307–311.
- 96 R. S. Lloyd et al., Curr. Med. Res. Opin. 13 (1992) 37–48.
- 97 Reckitt & Colman, DE 1 620 206, 1966.
- 98 Reckitt & Sons Ltd., US 3 433 791, 1969.
- 99 K. W. Bentley, D. G. Hardy, Proc. Chem. Soc. (London) 1963, 220.
- 100 W. G. Dorner, Chem. Unserer Zeit 15 (1986) 33–46.
- 101 K. O. Lee et al., Eur. J. Pharmacol. 378 (1999) 323–330.
- 102 G. F. Blane, J. Pharm. Pharmacol. 19 (1967) 367–373.
- 103 T. Alford et al., J. Am. Vet. Med. Ass. 164 (1974) 702–705.
- 104 G. Ehrhart, H. Ruschig: Arzneimittel, Entwicklung, Wirkung, Darstellung, vol. 1, Verlag Chemie, Weinheim 1972, pp. 119–120.
- 105 Knoll, DRP 607 931, 1935.
- 106 Z. R. Chen et al., Life Sci. 48 (1991) 2165–2171.
- 107 A. B. Morrison, Can. Med. Assoc J. 120 (1979) 1338.
- 108 Merck, US 2 715 626, 1955.
- 109 H. Rapoport, R. Naumann, E. R. Bissel, R. M. Bonner, J. Org. Chem. 15 (1950) 1103–1107.
- 110 G. Lindena et al., Schmerz 12 (1998) 195–204.
- 111 D. E. Moulin et al., Lancet 337 (1991) 465–468.
- 112 J. L. Hill, J. P. Zacny, Psychopharmacology (Berlin). 152 (2000) 31–39.
- 113 G. Ehrhart, H. Ruschig: Arzneimittel, Entwicklung, Wirkung, Darstellung, vol. 1, Verlag Chemie, Weinheim 1972, pp. 130–131.
- 114 O. Schnider, A. Grüssner, Helv. Chim. Acta 34 (1951) 2211–2217.
- 115 O. Schnider, J. Hellerbach, Helv. Chim. Acta 33 (1950) 1437–1448.
- 116 R. Grewe, Naturwissenschaften 33 (1946) 333–337.
- 117 L. L. Randall, G. Lehmann, J. Pharmacol. Exp. Ther. 99 (1950) 163.
- 118 S. W. Coniam, Anaesthesia 46 (1991) 518.
- 119 G. Ehrhart, H. Ruschig: Arzneimittel, Entwicklung, Wirkung, Darstellung, vol. I, Verlag Chemie, Weinheim 1972, 118.
- 120 E. Merck, DRP 411 530, 1925.
- 121 K. W. Bentley: The Chemistry of Morphine Alkaloids, Oxford 1954.
- 122 F. M. Hauser et al., J. Med. Chem. 17 (1974) 1117.
- 123 J. Cleary et al., J. Pharmacol. Exp. Ther. 271 (1994) 1528–1534.
- 124 E. Kalzo, A. Vanino, Clin Pharmacol. Ther. 47 (1990) 639–646.
- 125 F. Kaiko et al., Clin. Pharmacol. Ther. 59 (1996) 52–61.
- 126 U. Weiss, J. Am. Chem. Soc. 77 (1955) 5891–5892.
- 127 R. S. Sinatra, D. M. Harrison, Clin. Pharm. 8 (1989) 541–544.
- 128 V. S. Copland et al., Am. J. Vet. Res. 48 (1987) 1626–1630.
- 129 Winthrop, US 2 167 351, 1939, (O. Eisleb).
- 130 I. G. Farben, DE 679 281, 1937.
- 131
O. Eisleb,
Chem. Ber.
74
(1941)
1433–1450.
10.1002/cber.19410740814 Google Scholar
- 132 E. E. Smissman, G. Hite, J. Am. Chem. Soc. 81 (1959) 1201–1203.
- 133 C. B. Pert, S. H. Snyder, J. Med. Chem. 19 (1976) 1248–1250.
- 134 N. P. Fish, N. J. De-Angelis, Anal. Profiles Drug Subs. 1 (1972) 175–205.
- 135 K. Jiraki, Am. J. Forensic Med. Pathol. 13 (1992) 42–43.
- 136 D. Meyer, V. Halfin, J. Clin. Psychopharmacol. 1 (1981) 319–321.
- 137 C. F. Seifert, S. Kennedy, Pharmacotherapy 24 (2004) 776–783.
- 138 J. G. Stevenson et al., Jt. Comm. J. Qual. Saf. 30 (2004) 277–281, 233.
- 139 A. B. O'Connor, et al., Am. J. Med. 118 (2005) 885–889.
- 140 I.G. Farben, DRP 752 755, 1942.
- 141 H. Kägi, K. Miescher, Helv. Chim. Acta 32 (1949) 2489–2507.
- 142 C. B. Christensen, Pharmacol. Toxicol. 73 (1993) 344–345.
- 143 L. Jylli et al., Acta Anaesthesiol. Scand. 48 (2004) 1256–1259.
- 144 S. Andersen et al., Pain 67 (1996) 369–374.
- 145 P. Peltola, P. Soisalo, AMA Arch Intern Med. 101 (1958) 741–746.
- 146 Janssen, US 3 164 600, 1965; US 3 141 823, 1964.
- 147 R. Hess et al., J. Pharmacol. Exp. Ther. 179 (1971) 474–484.
- 148 M. A. Clotz, M. C. Nahata, Clin. Pharm. 10 (1991) 581–593.
- 149 J. F. Buchanan, C. R. Brown, Med. Toxicol. 3 (1988) 1–17.
- 150 Janssen, DE-OS 2 819 837, 1978.
- 151 F. Janssen et al., J. Med. Chem. 29 (1986) 2290–2297.
- 152
S. J. Hopkins,
Drugs Future
6
(1981)
335–337.
10.1358/dof.1981.006.02.1000238 Google Scholar
- 153 R. F. Cookson et al., Br. J. Anaesth. 55 Suppl 2 (1983) 147S–155S.
- 154 C. J. E. Niemegeers, P. A. J. Janssen, Drug. Dev. Res. 1 (1981) 83.
- 155 G. E. Larijani, M. E. Goldberg, Clin. Pharm. 6 (1987) 275–282.
- 156 Glaxo, EP 383 579, 1990.
- 157
Drugs Future
19
(1994)
1088–1092.
10.1358/dof.1994.019.12.276772 Google Scholar
- 158 K. Flick et al., Arzneim.-Forsch./Drug Res. 28 (1978) no. 1, 107–113.
- 159 W. E. Hoffman et al., Anesthesiology 79 (1993) 107–113.
- 160 T. E. Egan, Clin. Pharmacokinet. 29 (1995) 80–94.
- 161 F. Servin, Eur. J. Anaesthesiol. 15 Suppl.(1997) 41–44.
- 162 C. G. Haigh, Minerva Anesthesiol. 66 (2000) 414–416.
- 163 J. Cohen, D. l. Royston, Curr. Opin. Crit. Care 7 (2001) 227–231.
- 164 L. G. Michelsen et al., J. Clin. Anesth. 8 (1996) 679–682.
- 165 Janssen, US 3 998 834, 1976.
- 166
L. Castaner,
E. Arrigoni-Martelli,
Drugs Future
2
(1977)
334–337.
10.1358/dof.1977.002.05.53506 Google Scholar
- 167 W. F. M. Van Bever, et al., Arzneim.-Forsch./Drug Res. 26 (1976) 1548–1556.
- 168 P. G. H. Van Daele et al., Arzneim.-Forsch./Drug Res. 26 (1976) 1521–1531.
- 169 J. E. Leysen et al., Eur. J. Pharmacol. 87 (1983) 209–225.
- 170 I. P. Monk et al., Drugs 36 (1988) 286–313.
- 171 M. Goldberg et al., Anesthesiology 63 (1985) 199–201.
- 172 J. A. Grass, J. Pain Symptom Manage. 7 (1992) 271–286.
- 173 M. Goldberg et al., Anesthesiology 63 (1985) 199–201.
- 174 Farbw. Hoechst, DBP 865 314, 1941.
- 175 Merck & Co., US 2 644 010, 1953.
- 176 Abott, US 2 983 757, 1961.
- 177 E. M. Schultz et al., J. Am. Chem. Soc. 69 (1947) 2454–2459.
- 178 N. R. Easton et al., J. Am. Chem. Soc. 69 (1947) 2941–2942.
- 179 A. A. Larsen et al., J. Am. Chem. Soc. 70 (1948) 4195–4196.
- 180 E. E. Howe, M. Sletzinger, J. Am. Chem. Soc. 71 (1949) 2935.
- 181 M. Bockmühl, G. Ehrhart, Justus Liebigs Ann. Chem. 561 (1948) 52–85.
- 182 S. K. Sim, Can. Med. Assoc. J. 109 (1973) 615–619.
- 183
R. H. Biskara,
Anal. Profiles Drug Subs.
3
(1974)
365–439.
10.1016/S0099-5428(08)60074-X Google Scholar
- 184 M. P.xs Davis, D. Walsh, Support Care Cancer 9 (2001) 73–83.
- 185 H. Joseph et al., Mt. Sinai J. Med. 67 (2000) 347–364.
- 186
M. Farell
et al.,
Br. Med. J.
309
(1994)
997–1001.
10.1136/bmj.309.6960.997 Google Scholar
- 187 M. J. Kreek, JAMA. 223 (1973) 665–668.
- 188 J. Lowinson et al., Curr. Psychiatr. Ther. 18 (1978) 165–172.
- 189 F. I. Carroll et al., J. Org. Chem. 41 (1950) 3521–3524.
- 190 S. A. Walczak et al., Eur. J. Pharmacol. 72 (1981) 343–349.
- 191 J. D. Blaine et al. Ann. N. Y. Acad. Sci. 362 (1981) 101–115.
- 192 A. Wolven et al., NIDA Res. Monogr. (1976) 29–38.
- 193 J. Kang et al., Eur. J. Pharmacol. 458 (2003) 25–29.
- 194 R. L. Deamer et al., J. Addict Dis. 20 (2001) 7–14.
- 195 Janssen, DE 1 117 126; 1956; GB 822 055, 1956.
- 196 A. J. Grace, Br. Med. J. 281 (1980) 1285.
- 197 D. Boven et al., Hum. Toxicol. 3 (1984) Suppl., 1S–238S.
- 198 A. A. Lawson, D. B. Northridge, Med. Toxicol. Adverse Drug Exp. 2 (1987) 430–444.
- 199 Janssen, US 2 898 340, 1959; Searle, US 4 086 234, 1978.
- 200 C. J. Niemegeers et al., Arzneimittelforschung 22 (1972) 516–518.
- 201
D. D. Hung,
Anal. Profiles Drug. Subst.
7
(1978)
149–169.
10.1016/S0099-5428(08)60091-X Google Scholar
- 202 Janssen, US 3 714 159, 1973; ED-OS 2 126 559, 1971.
- 203 R. A. Stokbroekx et al., J. Med. Chem. 16 (1973) 782–786.
- 204 M. R. Dashwood et al., Prog. Clin. Biol. Res. 328 (1990) 165–169.
- 205 R. C. Heel et al., Drugs 15 (1978) 33–52.
- 206 R. C. Heel et al., Drugs. 15 (1978) 33–52.
- 207 D. L. DeHaven-Hudkins, et al., Life Sci. 71 (2002) 2787–2796.
- 208 F. Awouters et al., Dig. Dis. Sci. 38 (1993) 977–995.
- 209 C. D. Ericsson P. C. Johnson, Am. J. Med. 88(6A) (1990) 10S–14S.
- 210 Janssen, DE 1 238 472, 1961.
- 211 F. Weyne et al., Acta anaesth. belg. 19 (1968) 33–45.
- 212 Gödecke, DE 1 518 959, 1965; Warner-Lambert, US 3 557 126, 1969.
- 213 L. E. Overman et al., J. Org. Chem. 44 (1979) 4183–4185.
- 214 G. Satzinger, Justus Liebigs Ann. Chem. 758 (1972) 43–64, 65–71; 728 (1969) 64–87.
- 215 G. Satzinger et al., Pharm. Ind. 40 (1978) 657–664.
- 216 R. Schulz et al., Naunyn Schmiedebergs Arch. Pharmacol. 304 (1978) 89–93.
- 217 M. Hermann et al., Arzneimittel-Forsch. 20 (1970) 977–983.
- 218 K. O. Vollmer, Fortschr. Med. 106 (1988) 593–596.
- 219 Grünenthal, GB 997 399, 1964; US 3 564 100, 1971 (E. Frankus, K. Flick).
- 220 K. Flick et al., Arzneim.-Forsch./Drug Res. 28 (1978) no. 1, 107–113.
- 221 M. C. Frink et al., Arzneimittelforschung 46 (1996) 1029–1036.
- 222 E. Friderichs et al., Arzneimittel-Forsch. 28 (1978) 122–134.
- 223 R. B. Raffa, E. Friderichs, Pain Rev. 3 (1996) 249–271.
- 224 R. B. Raffa et al., J. Pharmacol. Exp. Ther. 267 (1993) 331–340.
- 225 C. R. Lee et al., Drugs 46 (1993) 313–340.
- 226 K. McClellan, L. J. Scott, Drugs 63 (2003) 1079–1088.
- 227 P. Huang et al., J. Pharmacol. Exp. Ther. 297 (2001) 688–695.
- 228 B. Kögel et al. Eur. J. Pain. 9 (2005) 599–611.
- 229 R. C. Heel et al., Drugs. 17 (1979) 81–110.
- 230
J. Martin,
J.Psychoactive Drugs Suppl
2
(2004)
129–137.
10.1080/02791072.2004.10400048 Google Scholar
- 231 S. Sung, J. M. Conry, Ann. Pharmacother. 40 (2006) 501–505.
- 232 T. J. Gal, Clin. Pharmacol. Ther. 45 (1989) 66–71.
- 233 N. Griessinger et al., Curr. Med. Res Opin. 21 (2005) 1147–1156.
- 234 A. Dahan et al., Br. J. Anaesth. (2006) 96, 627–632.
- 235 Bristol-Myers, US 3 775 414, 1973.
- 236 J. Monkovic et al., J. Am. Chem. Soc. 95 (1973) 7910.
- 237 J. Monkovic et al., J. Am. Chem. Soc. 100 (1978) 4609–4610.
- 238 C. E. Rosow, Acute Care 12 Suppl 1 (1988) 2–7.
- 239 R. C. Heel et al., Drugs 16 (1978) 473–505.
- 240 B. Ameer, F. J. Salter, Am. J. Hosp. Pharm. 36 (1979) 1683–1691.
- 241 R. V. Homan, Am. Fam. Physician 49 (1994) 188–192.
- 242 American Home, BE 776 173, 1971; DE 2 159 324, 1971.
- 243 M. E. Freed et al., J. Med. Chem. 16 (1973) 595–599.
- 244 J. C. Chen et al., Life Sci. 52 (1993) 389–396.
- 245 J. J. O'Brien, et al., Drugs 38 (1989) 226–248.
- 246 J. L. Malis, J. Pharmacol. Exp. Ther. 194 (1975) 488–498.
- 247 J. J. O'Brien, P. Benfield, Drugs 38 (1989) 226–248.
- 248 Wyeth, DE-OS 1 941 534, 1969; GB 1 285 025, 1969.
- 249 G. Bradley et al., Eur. J. Med. Chem. 15 (1980) 375.
- 250 B. Holmes, A. Ward, Drugs 30 (1985) 285–312.
- 251 G. W. Pasternak et al., Postgrad. Med. J. 61 Suppl 2 (1985) 5–12.
- 252 B. Holmes, A. Ward, Drugs 30 (1985) 285–312.
- 253 Endo Laboratories, GB 1 119 270, 1968; US 3 332 950, 1967.
- 254
L. Castaner,
P. J. Roberts,
Drugs Future
2
(1977)
613–615.
10.1358/dof.1977.002.09.277276 Google Scholar
- 255 E. B. De Souza, et al., J. Pharmacol. Exp. Ther. 244 (1988) 391–402.
- 256 J. K. Errick, R. C. Heel, Drugs 26 (1983) 191–211.
- 257 W. K. Schmidt, Drug Alcohol Depend. 14 (1985) 339–362.
- 258 G. C. Pugh et al., Br. J. Anaesth. 62 (1989) 601–609.
- 259 Merck & Co., US 2 364 833, 1944; US 2 891 954, 1959.
- 260 Sterling Drug, BE 611 000, 1961.
- 261 S. Archer et al., J. Med. Chem. 7 (1964) 123–127.
- 262 R. N. Brogden et al., Drugs 5 (1973) 6–91.
- 263 D. A. Reed, S. H. Schnoll, JAMA 256 (1986) 2562–2564.
- 264 H. Schmidthammer, Prog. Med. Chem. 35 (1998) 83–132.
- 265 G. Ehrhart, H. Ruschig: Arzneimittel, Entwicklung, Wirkung, Darstellung, vol .1, Verlag Chemie, Weinheim 1972, pp. 131–132.
- 266 J. Hellerbach et al., Helv. Chim. Acta 39 (1956) 429–440.
- 267 O. Schnider, A. Grüssner, Helv. Chim. Acta 24 (1951) 2211–2217.
- 268
D. M. Paton,
Drugs Future
4
(1979)
438–441.
10.1358/dof.1979.004.06.1002415 Google Scholar
- 269 W. Leimgruber et al., Adv. Biochem. Psychopharmacol. 8 (1973) 45–50.
- 270 F. F. Foldes et al., Can. Anaesth. Soc. J. 16 (1969) 151–161.
- 271 J. M. Evans et al., Anaesthesia 29 (1974) 721–727.
- 272 US 3 254 088, 1966; DE 1 183 508, 1962 (M. J. Lewenstein).
- 273 R. A. Olofson et al., Tetrahedron Lett. 1977 1567–1577.
- 274 R. Simantov, S. H. Snyder, Biochem. Soc. Trans. 5 (1977) 62–65.
- 275 K. A. Handal et al., Ann. Emerg. Med. 12 (1983) 438–445.
- 276 P. M. Goodrich, AANA J. 58 (1990) 14–16.
- 277 Endo Laboratories, GB 1 119 270, 1968; US 3 332 950, 1967.
- 278 V. Höllt, A. Herz, Fed. Proc. 37 (1978) 158–161.
- 279 B. L. Crabtree, Clin. Pharm. 3 (1984) 273–280.
- 280 J. P. Gonzalez, R. N. Brogden, Drugs 35 (1988) 192–213.
- 281 B. A. Judson et al., Drug Alcohol Depend. 7 (1981) 325–346.
- 282 Boehringer Ingelheim Pharma GmbH & Co. KG, US 4176186, 1979 (L. Goldberg, H. Merz, K. Stockhans).
- 283 C. S. Yuan, J. F. Foss, Neuropharmacology 38 (1999) 425–432.
- 284 C. S. Yuan et al., J. Pharmacol. Exp. Ther. 300 (2002) 118–123.
- 285 D. S. Wang et al., J. Emerg. Med. 16 (1998): 471–475.
- 286 H. E. Jones et al., Drug Alcohol Depend. 60 (2000) 29–37.
- 287 L. C. Costantini et al., Int. J. Pharm. 283 (2004) 35–44.
- 288 J. E. Grant et al., Am. J. Psychiatry 163 (2006) 303–312.
- 289 K. Hempenstall, A. S. Rice, Curr. Opin. Investig. Drugs 3 (220) 441–448.
- 290 R. H. Dworkin et al., Arch. Neurol. 60 (2003) 1524–1534.
- 291 H. Ueda, Pharmacol Therap. 109 (2006) 57–77.
- 292 D. B. Gordon, G. Love, Pain Manage. Nurs. 5 (2004) 19–33.
- 293 G. T. Carter, M. D. Sullivan, Curr. Opin. Investig. Drugs 3 (2002) 454–458.
- 294 J. Zhou, Drugs of the Future 29 (2004) 1235–1244.
- 295 J. Lai et al., Ann. Rev. Pharmacol. Toxicol. 44 (2004) 371–397.
- 296 Ciba, US 3 471 548. 1969.
- 297 Ciba, US 3 978 216, 1972.
- 298 N. G. Bowery, Curr. Opin. Pharmacol. 6 (2006) 37–43.
- 299 Geigi, US 2 948 718, 1960 (W. Schindler).
- 300 DD 133 052, 1977 (R. Müller).
- 301 D. Soyka et al., Schmerz 12 (1998) 419–427.
- 302 Boehringer Ingelheim, DE 1 303 141, 1961; US 3 236 857, 1966.
- 303 VEB Arzneimittelwerke Dresden, DE-AS 1 770 874, 1968.
- 304 H. Schmitt, Handb. Exp. Pharmacol. 39 (1977) 299–396.
- 305 C. Lund et al., Br. J. Anaesth. 63 (1989) 516–519.
- 306 D. R. Jasinki et al., Arch. Gen. Psychiatry 42 (1985) 1063–1066.
- 307 J. Deeter et al., Tetrahedron Lett. 31 (1990) 7101.
- 308 L. A. Sorbera et al., Drugs of the Future 25 (2000) 907–916.
- 309 H. Liu et al., Chirality 12 (2000) 26–29.
- 310 S. Attila, E. Leinonen, Curr. Opin. Investig.Drugs 3 (2002) 1217–1221.
- 311 N. Pitsikas, Curr. Opin. Investig. Drugs 1 (2000) 116–121.
- 312 Degussa, DE 1 795 858, 1968; US 3 513 171, 1970.
- 313
Drugs Future
8
(1983)
773–775.
10.1358/dof.1983.008.09.53539 Google Scholar
- 314 W. von Bebenburg et al., Chem. Ztg. 103 (1979) 387–399.
- 315 W. von Bebenburg et al., Chem. Ztg. 105 (1981) 217–219.
- 316 H. A. Friedel, A. Fitton, Drugs 45 (1993) 548–569.
- 317 Pfizer, US 4152326, (J. Hartenstein, G. Satziger).
- 318 Pfizer, US 4024175, (G. Satzinger, J. Hartenstein, M. Hermann, W. Heldt).
- 319 Zambon Group, WO 2005 044 779, 2005 (K. Arrighi, F. Corcella, G. Marchioro, A. Nicoli, M. Paiocchi, M. Villa).
- 320 Taro Pharmaceutical Industries Ltd., WO 2003 089403, 2003
- 321 R. Cagnoli et al., Tetrahedron 59 (2003) 9951.
- 322 G. J. Sills, Curr. Opin. Pharmacol. 6 (2006) 108–113.
- 323 J. K. Baille, I. Power Curr. Opin. Investig. Drugs 7 (2006) 33–39.
- 324 I. W. Tremont-Lukats et al., Drugs 60 (2000) 1029–1052.
- 325 J. Devulder et al., Acta Neurol. Belg. 102 (2002) 97–103.
- 326 Wellcome Foundation, EP 21 12, 1981 (M. G. Baxter, et al.).
- 327 Wellcome, US 4 560 687, 1985 (M. G. Baxter, A. R. Elphick, A. A. Miller, D. A. Sawyer).
- 328 Wellcome, US 4 602 017, 1986 (M. G. Baxter, A. R. Elphick, A. A. Miller, D. A. Sawyer).
- 329 E. Eisenberg et al., Rev. Neurotherapeutics 5 (2005) 729–735.
- 330 M. Guven, H. Bozdemir, J. Gunay, Y. Sarica, J. Kahraman, F. Koc, The actions of lamotrigine and levetiracetam on the conduction properties of isolated rat sciatic nerve, Eur. J. Pharmacol. 553 (2006), 129–134.
- 331 Rexall, US 3 487 153, 1969.
- 332 Riker, US 3 830 803, 1974.
- 333 R. C. Heel et al., Drugs 19 (1980) 249–267.
- 334 Park Davis, US 2 409 754, 1946 (H. R. Henze).
- 335 H. Biltz et al., Ber. Dtsch. Chem. Ges. 41 (1908) 1391.
- 336 Warner-Lambert WO 99/48876, 1999 (R. L. Bosch)
- 337
B. D. Maryanoff,
B. L. Margul,
Drugs of the Future
14
(1989)
342.
10.1358/dof.1989.014.04.85087 Google Scholar
- 338 B. E. Maryanoff, et al., Med. Chem. 30 (1987) 880–887.
- 339 Ortho-McNeil Pharmaceuticals Inc., US 4513006, 1985 (B. E. Maryanoff, J. F. Gardocki).
- 340 Ortho-McNeil Pharmaceuticals Inc., WO 2004 078769, 2004 (J. E. Berkner, S. Duncan)
- 341 C. E. Heading, IDrugs 4 (2001) 339–350.
- 342 C. E. Heading, Curr. Opin. Investig. Drugs 3 (2002) 915–920.
Further Reading
- J. K. Aronson: Meyler's Side Effects of Analgesics and Anti-inflammatory Drugs, Elsevier, Amsterdam 2010.
- P. Beaulieu, D. Lussier, F. Porreca, A. Dickenson: Pharmacology of Pain, IASP Press, Seattle 2010.
-
H. Buschmann et al.:
Analgesics-From Chemistry and Pharmacology to Clinical Application,
Wiley-VCH,
Weinheim
2002.
10.1002/3527605614 Google Scholar
- S. M. Fishman, J. C. Ballantyne, J. P. Rathmell (eds.): Bonica's Management of Pain, 4th ed., Lippincott Williams & Wilkins, Philadelphia 2009.
- E. Freye: Opioids in Medicine, Springer, Dordrecht 2008.