Antineoplastic and Immunomodulating Agents (L)
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Antineoplastic and Immunomodulating Agents (L)
First published: 19 June 2017
Abstract
The article contains sections titled:
| 1. | Introduction |
| 2. | Antineoplastic Agents (L01) |
| 2.1. | L01A Alkylating Agents |
| 2.2. | L01B Antimetabolites |
| 2.3. | L01C Plant Alkaloids and Other Natural Products |
| 2.4. | L01D Cytotoxic Antibiotics and Related Substances |
| 2.5. | L01X Other Antineoplastic Agents |
| 3. | Endocrine Therapy (L02) and Immunosuppressants (L04) |
| 3.1. | Endocrine Therapy (L02) |
| 3.2. | Immunosuppressants |
General References and Reviews
- Airley, R. (2009) Cancer Chemotherapy, Wiley-Blackwell, Chichester.
-
Missailidis, S. (2008) Anticancer Therapeutics, Wiley-Blackwell, Chichester
10.1002/9780470697047 Google Scholar
- National Cancer Institute (2015) What is Cancer?, www.cancer.gov/about-cancer/what-is-cancer (last accessed March 2017).
- Manley P. W., et al., (2015) Progress into the era of genomically targeted cancer drugs: 50 years of anticancer medicinal chemistry, in Medicinal Chemistry Reviews Vol. 50, Med. Chem. Division of the ACS, a) chapter 8, p. 187–223: Targeting Protein kinases, Lipid kinases, Protein-Protein interactions regulating apoptosis, aberrant DNA methylation, Histones, Hormones and hormone receptors, RAS. b) chapter 9, p. 225–237: Targeting the B-cell receptor pathway in hematological malignancies with Btk inhibitors, PI3Kδ inhibitors, Syk inhibitors.
- World Health Organisation (2017) Concentrate from World Cancer Report 2014, International agency for Research on Cancer (IARC) with data of the year 2012; www.who.int/mediacentre/factsheets/fs297/en/ (last accessed March 2017).
- World Health Organisation (2015) 19th WHO Model List of Essential Medicines, April 2015.
- IMS Institute for Healthcare Informatics: a) Global Oncology Trend Report, May 2015 (Development in cancer treatments, market dynamics, patient access and value); b) Global Oncology Trend Report, June 2016 (A review of 2015 and outlook to 2020).
- Dobbelstein, M. and Moll, U. (2014) Targeting tumour-supportive cellular machineries in anticancer drug development, Nature Rev. Drug Discov. 13, 179–196. (Review regarding also the history of cancer therapies).
- zur Hausen, H. (2009) The Search for Infectious Causes of Human Cancers: Where and Why (Nobel Lecture), Angew. Chem. Int. Ed. 48, 5798–5808
- Various authors (2009) Chemical Reviews 109, No.7, p. 2859–3208; 17 review articles on cancer chemotherapeutics.
- Cragg, G.M., et al. (2009) Impact of Natural Products on Developing New Anti-cancer Agents, Chemical Reviews 109, 3012–3043.
- NCA/NIH (Office of Cancer Nanotechnology Research, Center for Strategic Scientific Initiatives) (2015) Cancer Nanotechnology Plan 2015, 257 pages; (describes research results and challenges for the application of Nanotechnology to anticancer drug delivery and diagnostic methods, e.g., Manufacturing Challenges of Nano-Products).
- Various authors (2013) Nature outlook: Cancer Immunotherapy, Nature 504 (issue 7480), S1–S17.
- Adams, J.L., et al. (2015) Big opportunities for small molecules in immune-oncology, Nature Reviews Drug Discovery 14, 603–622.
- Al-Lazikani, B., et al. (2012) Combinatorial drug therapy for cancer in the post-genomic era, Nature Biotechnology 30, 1–13. (a detailed review)
- Zolot, R.S., et al. (2013) Antibody-drug conjugates, Nature Rev. Drug Discovery 12, 259–260.
Specific References
- 17 Kleemann-Engel-Kutscher-Reichert, (2009) Pharmaceutical Substances, 5th edn., 2009, Thieme Verlag Stuttgart and/or its online version.
- 18 Goodman & Gilman's (2011) The Pharmacological Basis of Therapeutics, 12th edn, McGraw Hill Medical, N.Y. et al.; Section VIII, Chemotherapy of Neoplastic Diseases, chapters 60-63, pages 1665–1769. – herein further referred to as Goodman & Gilman's.
- 19 Mutschler (2012) Arzneimittelwirkungen, 10th edn, Wissenschaftliche Verlagsgesellschaft, Stuttgart, chapter 22, Chemotherapie maligner Tumoren.
- 20
D.E.V. Wilman, (ed.) (1990) The Chemistry of Antitumour Agents, Blackie & Son Ltd., Glasgow and London.
10.1007/978-94-009-0397-5 Google Scholar
- 21 National Cancer Institute (2015) www.cancer.gov/ (last accessed March 2017).
- 22 Thayer, A.M, (2008) C&EN 86 (24), 17–27.
- 23 Goodman & Gilman's (2011) chapter 61/I, p. 1677–1690.
- 24
Sneader, W. (2005) Drug Discovery – A History, John Wiley & Sons, Chichester, p. 440–443. (History)
10.1002/0470015535 Google Scholar
- 25 Chabner, B.A. (2011) General Principles of Cancer Chemotherapy, in Goodman & Gilman's, p. 1667–1675.
- 26 Chabner, B.A., et al. (2011) Cytotoxic Agents in Goodman & Gilman's, p. 1677–1730.
- 27 Arnold, H. and Bourseaux, F. (1958) Angew. Chem. 70, 539.
- 28 Arnold, H., et al. (1958) Nature 181, 931.
- 29 Brock, N. (1962) Arzneim.-Forsch. 8, 1.
- 30 Asta-Werke (1962) US 3 018 302, DE-prior. 1956.
- 31 Everett, J.L., et al. (1953) J. Chem. Soc. 2390.
- 32 NRDC (1960) US 2 944 079, GB-prior. 1953.
- 33 NRDC (1962) US 3 032 584, GB-prior.
- 34 NRDC (1962) US 3 032 585, GB-prior. 1954.
- 35 Hanby W.E. and Rydon, H.N. (1947) J. Chem. Soc. 513.
- 36 Asta-Werke AG (1966) DE 1 645 921, DE-prior. 1966.
- 37 Asta-Werke AG (1973) US 3 732 340, DE-prior. 1967.
- 38 Ozegowski, W. and Krebs, D. (1963) J. prakt. Chem. 20 178.
- 39 Burroughs Wellcome (1959) US 2 917 432, GB-prior. 1950.
- 40 Sandberg J.S., et al. (1972) Cancer Chemother. Rep. Part 2, 30, 137.
- 41 American Cyanamid (1954) US 2 670 347, US-prior. 1952.
- 42 American Cyanamid (1990) US 4 918 199, US-prior. 1988.
- 43 Johnston, T.P., et al. (1963) J. Med. Chem. 6, 669; (1966) J. Med. Chem. 9, 892.
- 44 Johnston, T.P., et al. (1966) J. Med. Chem. 9, 892; (1975) J. Med. Chem. 18, 104.
- 45 Herr, R.R., et al. (1959–60) Antibiot. Ann. 230.
- 46 Herr, R.R. et al. (1967) J. Am. Chem. Soc. 89, 4808.
- 47 Upjohn (1962) US 3 027 300, US-prior. 1958.
- 48 Upjohn (1971) US 3 577 406, US-prior. 1968.
- 49 ADIR (Servier) (1986) US 4 567 169, FR-prior. 1982.
- 50 Sankyo (1977) US 4 003 901, JP-prior. 1971.
- 51 Tokyo Tanabe (1977) US 4 057 684, JP-prior. 1975.
- 52 Tokyo Tanabe (1979) US 4 156 777, JP-prior. 1977.
- 53 Stevens, M.F.G., et al. (1984) J. Med. Chem. 27, 196.
- 54 Cancer Res. Campaign Technol. (1993) US 5 260 291, GB-prior. 1981.
- 55 Schering Corp. (08.08.2006) US 7 087 751, US-prior. 18.01.2001.
- 56 Shealy, J.F., et al. (1962) J. Org. Chem. 27, 2150.
- 57 Goodman & Gilman's (2011) chapter 61/II, p. 1690–1705.
- 58 Jordheim, L.P., et al. (2013) Advances in the development of nucleoside and nucleotide analogues for cancer and viral diseases, Nature Rev. Drug Discovery 12, 447–464.
- 59 Shelton, J., et al. (2016) Metabolism, Biochemical Actions, and Chemical Synthesis of Anticancer Nucleosides, Nucleotides, and Base Analogs, Chem. Rev. 116, 14379–14455.
- 60 Seeger, D.R., et al. (1949) J. Am. Chem. Soc. 71, 1753.
- 61 Waller, C.W., et al. (1948). J. Am. Chem. Soc. 70, 19
- 62 Piper, J.R. and Montgomery, J.A. (1974) J. Heterocyclic. Chem. 11, 279.
- 63 Lederle (American Cyanamid) (1950) US 2 512 572, US-prior.1947.
- 64 Marsham, P.R., et al. (1991) J. Med. Chem. 34, 1594.
- 65 ICI (1991) US 4 992 550,GB-prior. 1986.
- 66 Taylor, E.C. et al. (1992) J. Med. Chem. 35, 4450.
- 67 Taylor, E.C. et al. (2003) J. Org. Chem. 68, 9938.
- 68 Trustees Princeton Univ. (1994) US 5 344 932, US-prior. 1989.
- 69 DeGraw, J.I. et al. (1993) J. Med. Chem. 36, 2228.
- 70 SRI (1994) US 5 354 751, US-prior. 1992.
- 71 Elion, G.B., et al. (1952) J. Am. Chem. Soc. 74, 411.
- 72 Burroughs Wellcome (1954) US 2 697 709, GB-prior. 1951.
- 73 Burroughs Wellcome (1956) US 2 756 228, GB-prior. 1954.
- 74 Elion, G.B. and Hitchings, G.H. (1955) J.Am.Chem Soc. 77, 1676.
- 75 Burroughs Wellcome (1954), US 2 697 709, GB-prior. 1951.
- 76 Burroughs Wellcome (1959) US 2 884 667, US-prior. 1955.
- 77 Christensen L.F., et al. (1972) J. Med. Chem. 15, 735.
- 78 Kazimerczuk, Z., et al. (1984) J. Am. Chem. Soc. 106, 6379.
- 79 Ortho Pharm. Corp. (1988) US 4 760 137, US-prior. 1984.
- 80 Ortho Pharm. Corp. (1993) US 5 208 327, US-prior. 1991.
- 81 Montgomery, J.A., et al. (1969) J. Med. Chem. 12, 498.
- 82 Montgomery, J.A., et al. (1979) J. Heterocycl. Chem. 16, 157.
- 83 DoH (1980) US 4 210 745, US-prior. 1978.
- 84 DoH (1982) US 4 357 324, US-prior. 1981.
- 85 Schering AG (1997) US 5 602 246, US-prior. 1992.
- 86 Montgomery, J.A., et al. (1992) J. Med. Chem. 35, 397.
- 87 Bauta, W.E., et al. (2004) Org. Process Res. & Dev. 8, 889.
- 88 Sloan-Kettering Inst. Cancer Research (1988) US 4 751 221, US-prior. 1985.
- 89 Sloan-Kettering Inst. Cancer Research (1990) US 4 918 179, US-prior. 1985.
- 90 Ilex Products (20.01.2004) US 6 680 382, US-prior. 02.08.2001.
- 91 Burroughs Wellcome (1995) US 5 424 295, GB-prior. 1987.
- 92 Shen, T.Y., et al. (1965) J. Org. Chem. 30, 835.
- 93 Upjohn (1963) US 3 116 282, US-prior. 1956.
- 94 Duschinsky, R., et al. (1957) J. Am. Chem. Soc. 79, 4559.
- 95 Roche (1957) US 2 802 005, US-prior. 1956.
- 96 Barton, D.H.R., et al. (1972) J. Org. Chem. 37, 329.
- 97 Knuniants, I.L., et al. (1972) US 3 682 917, US-prior. 1970.
- 98 Yasumoto, M., et al. (1977) J. Med. Chem. 20, 1592.
- 99 Yasumoto, M., et al. (1978) J. Med. Chem. 21, 738.
- 100 Giller, S.A., et al. (1972) US 3 635 946, US-prior. 1967.
- 101 Hertel, L.W.. et al. (1988) J. Org. Chem. 53, 2406.
- 102 Eli Lilly (1985) US 4 526 988, US-prior. 1983.
- 103 Eli Lilly (1989) US 4 808 614, US-prior. 1983.
- 104 Cook, A.F., et al. (1979) J. Med. Chem. 22, 1330.
- 105 Roche (1995) US 5 472 949, EP-prior. 1992.
- 106 Piskala, A. and Sorm, F. (1964) Collect. Czech. Chem. Commun. 29, 2060.
- 107 Piskala, A. and Sorm, F. (1967) US 3 350 388, US-prior. 1965.
- 108 Pliml, J. and Sorm, F. (1964) Collect. Czech. Chem. Commun. 29, 2576.
- 109 Dumontet, C. and Jordan, M.A. (2010) Microtubule-binding agents: a dynamic field of cancer therapeutics, Nature Rev. Drug Discovery 9, 790–803.
- 110 Goodman & Gilman's (2011), Microtubule-damaging agents, chapter 61/III, p. 1705–1730.
- 111 Noble, R.L. et al. (1958) Ann. N. Y. Acad. Sci. 76, 882.
- 112 Gorman, M., et al. (1959) J. Am. Chem. Soc. 81, 4745, 4754.
- 113 Canadian Pat.&Dev. (1963) US 3 097 137, US-prior. 1958.
- 114 Eli Lilly (1965) US 3 225 030, US-prior. 1958.
- 115 Richter Gedeon (1978) US 4 070 358, H-prior. 1975.
- 116 Lilly (1965) US 3 205 220, US-prior. 1961. (Extraction).
- 117 Richter Gedeon (1975) US 3 899 493, US-prior. 1972. (Semisynthesis from vinblastine by oxidation).
- 118 Burnett, C.J., et al. (1978) J. Med. Chem. 21, 88.
- 119 Eli Lilly (1980) US 4 203 898, US-prior. 1973.
- 120 Eli Lilly (1984) US 4 479 957, US-prior. 1973.
- 121 Mangeney, P., et al., (1979) J. Org. Chem. 44, 3765.
- 122 ANVAR (1981) US 4 307 100, FR-prior. 1978.
- 123 Raucher, S., et al. (1987) J. Am. Chem. Soc. 109, 442.
- 124 Lilly (1977) US 4 029 663, US-prior. 1975.
- 125 Fahy, J., et al. (1997) J. Am. Chem. Soc. 119, 8576.
- 126 Pierre Fabre (15.04.1997) US 5 620 985, FR-prior. 21.07.1993.
- 127 Keller-Juslen, C., et al. (1971) J. Med. Chem. 14, 936.
- 128 Sandoz (1970) US 3 524 844, CH-prior. 1965.
- 129 Wang, Y.-F., et al. (2011) Natural Taxanes: developments since 1828, Chem. Rev. 111, 7652–7709.
- 130 Wani, M.C. et al. (1971) J. Am. Chem. Soc. 93, 2325.
- 131 Denis, J.N., et al. (1988) J. Am. Chem. Soc. 110, 5917.
- 132 Holton, R.A., et al. (1993) Bioorg. Med. Chem. Lett. 3, 2475.
- 133 Florida State Univ. (1993) US 5 254 703, US-prior. 1992.
- 134 Singh, A.K., et al. (2003) Org. Proc. Res. Dev. 7, 25.
- 135 Phyton Biotech (04.09.2007) US 7 264 951, US-prior. 20.02.1992
- 136 Gueritte-Voegelein, F., et al. (1992) J. Med. Chem. 34, 992.
- 137 Rhone-Poulenc Rorer (1989) US 4 814 470, FR-prior. 1986.
- 138 Rhone-Poulenc Rorer (1988) EP 253 738, FR-prior. 1986.
- 139 Rhone Poulenc Rorer; Aventis (08.12.1998) US 5 847 170, FR-prior. 27.03.1995.
- 140 Rhone Poulenc Rorer; Aventis (28.03.2002) US 6 387 946, FR-prior. 27.03.1995.
- 141 Rinehart, K.L., et al. (1990) J. Org. Chem. 55, 4512.
- 142 Corey, E.J., et al. (1996) J. Am. Chem. Soc. 118, 9202.
- 143 Univ. Illinois (1992) US 5 089 273, US-prior. 1986.
- 144 PharmaMar (10.04.2007) US 7 202 361, GB-prior. 12.04.2000.
- 145 Merck & Co. (1945) US 2 378 876, US-prior. 1941.
- 146 Arcamone, F., et al. (1975) J. Med. Chem. 18, 703.
- 147 Farmitalia (1971) US 3 590 028, IT-prior. 1967.
- 148 Arcamone, F., et al. (1964) J. Am. Chem. Soc. 86, 5334.
- 149 Farmitalia (1977) US 4 012 284, IT-prior. 1962.
- 150 Arcamone, F., et al. (1975) J. Med. Chem. 18, 703.
- 151 Farmitalia (1977) US 4 058 519, IT-prior. 1974.
- 152 Farmitalia (1977) US 4 046 878, GB-prior. 1974.
- 153 Adria Labs. (1984) US 4 471 052, US-prior. 1982.
- 154 Murdock, K.C., et al. (1979) J. Med. Chem. 22, 1024.
- 155 Zee-Cheng, R.K.-Y., and Cheng, C.C. (1978) J. Med. Chem. 21, 291.
- 156 American Cyanamid (1980) US 4 197 249, US-prior. 1977.
- 157 American Cyanamid (1981) US 4 278 689, US-prior. 1978.
- 158 S.Farber Cancer Institute (1977) US 4 035 566, US-prior. 1975.
- 159
Nicolaou, K.C., et al. (1998) Chemical biology of Epothilones, Angew. Chem. Internat. Ed.
37, 2014–2045.
10.1002/(SICI)1521-3773(19980817)37:15<2014::AID-ANIE2014>3.0.CO;2-2 CAS PubMed Web of Science® Google Scholar
- 160 Umezawa, H., et al., (1966) J. Antibiot. 19, 200; 210.
- 161 Takita, T., et al. (1968) J. Antibiot. 21, 79; (1969) J. Antibiot. 22, 237; (1972) J. Antibiot. 25, 755; (1978) J. Antibiot. 31, 801.
- 162 Microb. Chem. Res. Found. (1980) US-RE 30 451, JP-prior. 1969.
- 163 Hata, T., et al. (1956) J. Antibiot. 9A, 141.
- 164 Kyowa Hakko (1972) US 3 660 578, JP-prior. 1957.
- 165 Stevens, C.L., et al. (1965) J. Med. Chem. 8, 1.
- 166 Borzilleri, R.M., et al. (2000) J. Am. Chem. Soc. 122, 8890.
- 167 Bristol-Myers Squibb (BMS) (12.08.2003) US 6 605 599, US-prior. 08.07.1997.
- 168 Wilson, J.J. and Lippard, S.J. (2014) Synthetic methods for the preparation of platinum anticancer complexes, Chem. Rev. 114, 4470–4495.
- 169
Peyrone, M. (1845) Annalen
51, 1.
10.1002/jlac.18440510102 Google Scholar
- 170 Rosenberg, B., et al. (1965) Nature 205, 698.
- 171 MPD Technol. (1981) US 4 273 755, US-prior.1979.
- 172 Research Corp. (1979) US 4 140 707, US-prior. 1972.
- 173 Kidani, Y. and Inagaki, K. (1978) J. Med. Chem. 21, 1315.
- 174 Kidani, Y. and Inagaki, K. (1979) US 4 169 846, JP-prior. 1976.
- 175 Roche (1970) US 3 520 926, CH-prior. 1961.
- 176 Celli, J.P., et al. (2010) Imaging and photodynamic therapy: mechanisms, monitoring, and optimization, Chem. Rev. 110, 2795–2838.
- 177 Lovell, J.F., et al. (2010) Activatable photosensitizers for imaging and therapy, Chem. Rev. 110, 2839–2857.
- 178 Health Research Inc. (1987) US 4 649 151, US-prior. 1982.
- 179 Univ. B.C. (1988) US 4 883 790, US-prior. 1987.
- 180 Univ. B.C. (1992) US 5 095 030, CA-prior. 1988.
- 181 Quadra Logic (1991) US 5 053 423, USA-prior. 1990.
- 182 Quadra Logic (1993) US 5 238 940, USA-prior. 1990.
- 183 Siddiqui, M.A.A., et al. (2004) Am. J. Clin. Dermatol. 5, 127. (Review).
- 184 Queen's Univ. (1993) US 5 234 940, US-prior.1989.
- 185 Bonnett, R. et al. (1989) Biochem. J. 261, 277.
- 186 Bonnett, R. and Martinez, G. (2002) Org. Lett. 4, 2013.
- 187 Efamol (1991) US 4 992 257, GB-prior. 1988.
- 188 Parrish, J.A. et al. (1980) Int. J. Dermatol. 19, 379. (Use).
- 189 US Secret. Agricult. (1959) US 2 889 337, US-prior. 1956. (Extraction).
- 190 Elder, T.C. (1978) US 4 129 576, US-prior. 1976. (Synthesis).
- 191 Kleemann, A. (2010) Ullmann's Chapter “Antineoplastic Agents 1”, pp. 44–49..
- 192 Capdeville, R. et al. (2002) Glivec (STI 571, Imatinib), a rationally developed, targeted anticancer drug, Nature Rev. Drug Discovery 1, 493.
- 193 Goodman & Gilman's (2011), chapter 62, p. 1731–1740.
- 194 Bradshaw, T.D. (2008) Target-Directed Drug Discovery, in S. Missailidis (ed.), Anticancer Therapeutics, Wiley-Blackwell, Oxford, pp. 223–243.
- 195 Airley, R. (2009) Tyrosine kinase inhibitors, in Cancer Chemotherapy chapter 14, Wiley-Blackwell, Oxford, pp. 217–223.
- 196 Bridges, A.J. (2001) Chemical Inhibitors of Protein Kinases, Chem. Rev. 101 2541–2571.
- 197 Jänne P.A, et al. (2009) Factors underlying sensitivity of cancers to small-molecule kinase Inhibitors, Nature Rev. Drug Discovery 8 709–723.
- 198 Bikker J.A., et al. (2009) Kinase domain mutations in cancer: implications for small molecule drug design strategies, J. Med. Chem. 52 1493–1509.
- 199 Peták, I. et al. (2010) Integrating molecular diagnostics into anticancer drug discovery, Nature Rev. Drug Discovery 9 523–535.
- 200 Morphy, R. (2010) Selectively nonselective kinase inhibition: striking the right balance, J. Med. Chem. (Perspective) 53 1413–1437.
- 201 Davis, M.I. et al. (2011) Comprehensive analysis of kinase inhibitor selectivity, Nature Biotechnol. 29 1046–1052.
- 202 Barf, T. and Kaptein, A. (2012) Irreversible protein kinase inhibitors: balancing the benefits and risks, J. Med. Chem. 55 6243–6262.
- 203 Musumeci F., et al. (2012) Vascular Endothelial growth factor (VEGF) receptors: drugs and new inhibitors, J. Med. Chem. 55 10797–10822.
- 204 Cui, J.J (2014) A new challenging and promising era of Tyrosine kinase inhibitors, ACS Med. Chem. Lett. 5 272–274.
- 205 Fruman, D.A. and Rommel, Ch. (2014) P13K and cancer: lessons, challenges and opportunities, Nature Rev. Drug Discovery 13 140–156.
- 206 Various authors (2015) J. Med. Chem. 58 1–521: special issue “New frontiers in Kinases”.
- 207 Asghar U., et al. (2015) The history and future of targeting cyclin-dependent kinases (CDKs) in cancer therapy, Nature Rev. Drug Discovery 14 130–146.
- 208 Myers S.H., et al. (2016) AXL inhibitors in cancer: a medicinal chemistry perspective, J. Med. Chem. 59 3593–3608.
- 209 Cohen, P. and. Alessi, D.R. (2013) Kinase drug discovery – what's next in the field?, ACS Chem. Biol. 8 96–104.
- 210 Zimmermann, J. et al. (1997) Bioorg. Med. Chem. Lett. 7, 187.
- 211 Capdeville R., et al. (2002) Nature Rev. Drug Discov. 1, 493.
- 212 Ciba-Geigy (1996) US 5 521 184, US-prior. 1993.
- 213 Barker, A.J. et al. (2001) Bioorg. Med. Chem. Lett. 11, 1911.
- 214 Zeneca (23.06.1998) US 5 770 599, GB-prior. 27.04.1995.
- 215 Pfizer (05.05.1998) US 5 747 498, US-prior. 28.05.1996.
- 216 Dowell, J., et al. (2005) Nature Rev. Drug Discov. 4, 13.
- 217 Sun, L., et al. (2003) J. Med. Chem. 46, 1116.
- 218 Manley, J.M., et al. (2003) J. Org. Chem. 68, 6447.
- 219 Atkins, M.. et al. (2006). Nature. Rev. Drug Discov. 5, 279.
- 220 Sugen (11.08.1998) US 5 792 783, US-prior. 07.06.1995.
- 221 Bankston, D., et al. (2002) Org. Process Res. Dev. 6, 777.
- 222 Wilhelm, S.. et al. (2006) Nature Rev. Drug Discov. 5, 835.
- 223 Bayer (26.06.2007) US 7 235 576, US-prior. 12.01.2001.
- 224 Bayer (01.08.2008) US 7 351 834, US-prior. 13.01.1999.
- 225 Lombardo, L.J., et al. (2004) J. Med. Chem. 47, 6658.
- 226 Kantarjian, H., et al. (2006) Nature Rev. Drug Discov. 5, 717.
- 227 Bristol-Myers Squibb (22.07.2003) US 6 596 746, US-prior. 15.04.1999.
- 228 Moy, B. et al. (2007) Nature Rev. Drug Discov. 6, 431.
- 229 SmithKline Beecham; GlaxoSmithKline (19.09.2006) US 7 109 333, GB-prior. 12.01.1998.
- 230 Quintás-Cardama, A., et al. (2007) Nature Rev. Drug Discov. 6, 834.
- 231 Storey, S. (2009) Nature Rev. Drug Discov. 8, 447.
- 232 Novartis (30.01.2007) US 7 169 791, GB-prior. 05.07.2002, 20.12.2002.
- 233 AHP (08.11.1994) US 5 362 718, US-prior. 18.04.1994.
- 234 Wyeth (21.08.2001) US 6 277 983, US-prior. 27.09.2000.
- 235 Sandoz (09.09.1997) US 5 665 772, GB-prior. 09.10.1992.
- 236 American Home Products (21.08.2001) US 6 277 983, US-prior. 27.09.2000.
- 237 Bukowski, R.M., et al. (2010) Nature Rev. Drug Discov. 9, 17.
- 238 Harris, P.A., et al. (2008) J. Med. Chem. 51, 4632.
- 239 SKB (12.09.2006) US 7 105 530, US-prior. 21.12.2000.
- 240 SKB (28.08.2007) US 7 262 203, US-prior. 21.12.2000.
- 241 GSK (14.02.2012) US 8 114 885, US-prior. 21.12.2000.
- 242 Hennequin, L.F., et al. (2002) J. Med. Chem. 45, 1300.
- 243 AstraZeneca (06.02.2007) US 7 173 038, EP-prior. 05.11.1999.
- 244 Boehringer Ing (29.05.2012) US RE 43 431, DE-prior. 20.12.2000.
- 245 Boehringer Ing (28.03.2006) US 7 019 012, DE-prior. 20.12.2000.
- 246 Boschelli, D.H., et al. (2001) J. Med. Chem. 44, 3965; (2004) J. Med. Chem 47, 1599.
- 247 American Cyanamid (14.12.1999) US 6 002 008, US-prior. 03.04.1997.
- 248 Bollag, G., et al. (2010) Nature 467, 596.
- 249 Bollag, G., et al. (2012) Nature Rev. Drug Discov. 11, 873.
- 250 Plexxikon (04.01.2011) US 7 863 288, USA-prior. 22.06.2005 [661 pages]
- 251 Plexxikon (27.03.2012) US 8 143 271; USA-prior. 22.06.2005 [670 pages]
- 252 Shaw, A.T.. et al. (2011) Nature Rev. Drug Discov. 10, 897.
- 253 Cui, J.J., et al. (2011) J. Med. Chem. 54, 6342.
- 254 Agouron (28.12.2010) US 7 858 643, US-prior. 26.08.2004.
- 255 de Koning, P.P., et al. (2011) Org. Process Res. Dev. 15, 1018.
- 256 Agouron (25.10.2001) US 6 534 524, US-prior. 02.07.1999.
- 257 Agouron (19.06.2007) US 7 232 910, US-prior. 02.11.2004.
- 258 Xiang, Y., et al. (2008) Org. Process Res. Dev. 12, 116.
- 259 Flahive, E.J., et al. (2008) Org. Process Res. Dev. 12, 637.
- 260 Chekal, B.P., et al. (2009) Org. Process Res. Dev. 13, 1327.
- 261 Mesa, R.A., et al. (2012) Nature Rev. Drug Discov. 11, 103.
- 262 Moran, N. (2012) Nature Biotechnol. 30, 3.
- 263 Incyte (06.10.2009) US 7 598 257, US-prior. 13.12.2005.
- 264 Bayer (03.02.2005) WO 2005/009961, US-prior. 23.07.2003.
- 265 Bayer (01.04.2008) US 7 351 834, US-prior. 13.01.1999.
- 266 Bankston, D., et al. (2002) Org. Process Res. Dev. 6, 777.
- 267 Rheault, T.R., et al. (2013) Med. Chem. Lett. 4, 358.
- 268 GSK (09.08.2011) US 7 994 185, US-prior. 06.05.2008.
- 269 GSK (09.04.2013) US 8 415 345, US-prior. 14.07.2011.
- 270 Huang, W.-S., et al. (2010) J. Med. Chem. 53, 4701.
- 271 Ariad Pharmaceuticals (14.02.2012) US 8 114 874, US-prior. 22.12.2006.
- 272 Abe, H., et al. (2011) Med. Chem. Lett. 2, 320.
- 273 Japan Tobacco (27.05.2013) US 7 378 423, JP-prior. 11.06.2004,10.11.2004.
- 274 Exelixis (25.08.2009) US 7 579 473, US-prior. 26.09.2003.
- 275 Exelixis (15.05.2012) US 8 178 532, US-prior. 09.01.2004.
- 276 Young, R.M., et al. (2013) Nature Rev. Drug Disc. 12, 229.
- 277 Pharmacyclics (07.04.2009) US 7 514 444, US-prior. 22.09.2006.
- 278 Pharmacyclics (19.03.2013) US 8 399 470, US-prior. 22.09.2006.
- 279 Chen, J., et al. (2013) J. Med. Chem. 56, 5673.
- 280 Marsilje, T.H., et al. (2013) J. Med. Chem. 56, 5675.
- 281 Novartis (22.02.2011) US 7 893 074, GB-prior. 15.08.2003.
- 282 Novartis (21.06.2011) US 7 964 592, GB-prior. 14.03.2003.
- 283 Cully, M. (2015) Nature Rev. Drug Discov. 14, 229.
- 284 Eisai (07.08.2007) US 7 253 286, JP-prior. 20.10.2000.
- 285 Eisai (03.11.2009) US 7 612 208, JP-prior. 25.12.2003.
- 286 Roth, G.J.. et al. (2009) J. Med. Chem. 52, 4466.
- 287 Roth, G.J., et al. (2015) J. Med. Chem. 58, 1053.
- 288 Boehringer Ing (13.07.2003) US 6 762 180, DE-prior. 13.10.1999.
- 289 VanderWel, S.N., et al. (2005) J. Med. Chem. 48, 2371.
- 290 Toogood, P.L., et al. (2005) J. Med. Chem. 48, 2388.
- 291 Maloney, M.T., et al., (2016) OPRD 20, 1191, 1203, 1217. (Commercial process).
- 292 Warner-Lambert (30.08.2005) US 6 936 612, USA-prior. 22.01.2002.
- 293 Pfizer (24.08.2010) US 7 781 583, USA-prior. 08.09.2006.
- 294 Finlay, M.R.V., et al. (2014), J. Med. Chem. 57, 8249–8267. (Synthesis).
- 295 AstraZeneca (31.01.2013) WO 2013/ 014448, USA-prior. 27.07.2011.
- 296 AstraZeneca (03.02.2015) US 8 946 235, USA-prior. 07.07.2011.
- 297 Kinoshita, K., et al. (2012) Bioorganic & Medicinal Chemistry 20, 1271.
- 298 Chugai (08.09.2015) US 9 126 931JP-prior. 10.06.2009.
- 299 Chugai (14.06.2016) US 9 365 514, JP-prior. 20.08.2010.
- 300 Rice, K. D., et al. (2012) Med. Chem. Letter 3, 416–421. (Synthesis).
- 301 Exelixis (28.09.2010) US 7 803 839, USA-prior. 07.10.2005.
- 302 Exelixis (29.01.2013) US 8 362 002, USA-prior. 07.10.2005.
- 303 Paris, M., et al. (2008) Histone deacetylase (HDAC) inhibitors: from bench to clinic, J. Med. Chem. 51, 1505–1529. – [incl. Vorinostat, Romidepsin, Panobinostat, Belinostat].
- 304 Rentsch, A., et al. (2013) Synthesis and pharmacology of Proteasome inhibitors, Angew. Chem. Internat. Ed. 52, 5450–5488. [incl. Bortezomib, Carfilzomib, Ixazomib].
- 305 Jackson, K.L., et al. (2009) The Halichondrins and E7389, Chem. Rev. 109, 3044–3079. [Eribulin].
- 306 Cain, B.F., et al. (1975) J. Med. Chem. 18, 1110.
- 307
Hofmann, A.W. (1885) Ber.
18, 2755.
10.1002/cber.188501802188 Google Scholar
- 308 Cassella (1969) US 3 424 752 DE-prior. 1965.
- 309 Dressler, W.F.C. et al. (1869), Ann. 150, 242.
- 310 Du Pont (1955) US 2 705 727 US-prior. 1952.
- 311 Woo, P.W.K., et al. (1974) J. Heterocycl. Chem. 11, 641.
- 312 Parke Davis (1975) US 3 923 785, US-prior. 1974.
- 313 Warner-Lambert (1995) US 5 463 035 US-prior. 1991.
- 314 ASTA Medica (1997) EP 521 297, DE-prior. 1991.
- 315 MPG (1989) US 4 837 023, DE-prior. 1985 and 1986.
- 316 Leo (1977) US Re 29199, GB-prior. 1963. [reissue of US 3 299 104]
- 317 Roche (1973) US 3 746 730, CH-prior. 1969.
- 318 Kingsbury, W.D., et al. (1991) J. Med. Chem. 34, 98.
- 319 SmithKline Beecham (1991) US 5 004 758, US-prior. 1987.
- 320
Sawada, S., et al. (1986) Chem. Pharm. Bull.
39, 1446.
10.1248/cpb.39.1446 Google Scholar
- 321 Yakult Honsha (1986) US 4 604 463, JP-prior. 1983.
- 322 Robeson, C.D., et al. (1955) J. Am. Chem. Soc. 77, 4111.
- 323 Boehm, M.F., et al. (1994) J. Med. Chem. 37, 408.
- 324 Bennani, Y.L. (1996) J. Org. Chem. 61, 3542.
- 325 Terzolo, M., et al. (2007) N. Engl. J. Med. 356, 2372.
- 326 Hailer, B.L., et al. (1945) J. Am. Chem. Soc. 67, 1591. (Synthesis).
- 327 Soignet, S.L., et al. (1998) N. Engl. J. Med. 339, 1341.
- 328 Miller, W.H., et al. (2002) Cancer Res. 62, 3893.
- 329 Memorial Sloan Kettering Cancer Center (20.04.2004) US 6 723 351,; US-prior. 10.11.1997.
- 330 Boehm, M.F., et al. (1994) J. Med. Chem. 37, 2930.
- 331 Ligand Pharmac. (14.07.1998) US 5 780 676, US-prior. 22.04.1992.
- 332 Adams, J., et al. (1998) Bioorg. Med. Chem. Lett. 8, 333.
- 333 Millennium Pharmac (14.07.1998) US 5 780 454, US-prior. 28.10.1994.
- 334 Millennium Pharmac (08.06.2004) US 6 747 150, US-prior. 28.10.1994.
- 335 Yamaguchi, H., et al. (1981) J. Heterocycl. Chem. 18, 67.
- 336 Roberts Lab. (08.03.1996) EP 778 258 US-prior. 04.12.1995.
- 337 Bristol-Myers (1976) US 3 932 407 US-prior. 1972.
- 338 Stowell, J.C., et al. (1995) J. Med. Chem. 38, 1411.
- 339 Sloan-Kettering Inst.Cancer Res. (29.11.1994) US 5 369 108, US-prior. 04.10.1991.
- 340 Okuhara, M., et al. (1994) J. Antibiot. 47, 301.
- 341 Fujisawa (1990) US 4 977 138, GB-prior. 1988.
- 342 ChemGenex (09.07.2009) US 2009/0176759, US-prior. 07.12.2007.
- 343 Stragen (30.01.2007) US 7 169 774 FR-prior. 20.03.1998.
- 344 Zheng, W., et al. (2004) Bioorg. Med. Chem. Lett. 14, 5551.
- 345 Eisai (10.04.2001) US 6 214 865, US-prior. 17.06.1998.
- 346 Eisai (30.12.2008) US 7 470 720, US-prior. 16.10.2002.
- 347 Guha, M. (2015) Nature Rev. Drug Discov. 14, 225.
- 348 Novartis (22.04.2003) US 6 552 065, USA-prior. 01.09.2000.
- 349 Novartis (01.11.2014) US 8 883 842, USA-prior. 03.08.2005). (Medical use in multiple myeloma).
- 350 Gianetti, A.M., et al. (2011) J. Med. Chem. 54(8), 2592.
- 351 Curis (15.02.2011) US 7 888 364, USA-prior. 02.09.2004.
- 352 Zhou, H.J., et al. (2009) J. Med. Chem. 52, 3028.
- 353 Proteolix (19.06.2007) US 7 232 818, USA-prior. 15.04.2004.
- 354 Menear, K.A., et al. (2008) J. Med. Chem. 51, 6581.
- 355 Kudos (19.12.2006) US 7 151 102, GB-prior. 30.10.2000.
- 356 Kudos (22.05.2012) US 8 183 369, USA-prior. 17.10.2007.
- 357 Patel, L., et al. (2016) J. Med. Chem. 59, 3532.
- 358 ICOS (05.10.2004) US 6 800 620, USA-prior. 25.04.2000.
- 359 ICOS (26.04.2011) US 7 932 260 USA-prior. 13.05.2004.
- 360 ICOS (12.11.2013) US RE 44 599 USA-prior. 13.05.2004.
- 361 ICOS (10.12.2013) US RE 44 638 USA-prior. 13.05.2004.
- 362 Pan, S., et al. (2010) ACS Med. Chem. Lett. 1, 130.
- 363 Novartis (22.11.2011) US 8 063 043, USA-prior. 17.09.2008.
- 364 IRM LLC (15.05.2012) US 8 178 563, USA-prior. 05.05.2006.
- 365 Topo Target (03.05.2005) US 6 888 027, GB-prior. 29.09.2000.
- 366 Formulation: Topo Target (16.09.2014) US 8 835 501, USA-prior. 13.05.2005. (Formulation).
- 367 Chizkov, R.R., and Million, R.P. (2015) Nature Rev. Drug Discov. 14, 597.
- 368 Millenium Pharm. (28.10.2008) US 7 442 830, USA-prior. 06.08.2007.
- 369 Millenium Pharm. (10.09.2013) US 8 530 694, USA-prior. 06.08.2007.
- 370 Bruncko, M., et al. (2007) J. Med. Chem. 50, 641–662. (Synthesis).
- 371 Abbvie (01.10.2013) US 8 546 399, US-prior. 26.05.2009 – see ex.1, p. 107–112.
- 372 Goodman & Gilman's (2011) chapter 63, p. 1755–1769.
- 373 Airley, R. (2009) Cancer Chemotherapy, Wiley-Blackwell, Chichester, p. 106 ff.
- 374
Sneader, W. (2005) Drug Discovery–A History, Wiley, Chichester, p. 195 ff.
10.1002/0470015535 Google Scholar
- 375 Fernö, O., et al. (1958) Acta Chem. Scand. 12, 1675.
- 376 AB Leo (1960) US 2 928 849, DK-prior. 1953.
- 377 Inhoffen, H.H., et al. (1938) Ber. Dtsch. Chem. Ges. 71, 1024.
- 378 Inhoffen, H.H., et al. (1938) Naturwissenschaften 26, 96.
- 379 Schering (1941) US 2 243 887, DE-prior. 1935.
- 380 Schering (1941) US 2 251 939, FR-prior. 1935.
- 381 Schering (1941) US 2 265 976, DE-prior. 1937.
- 382 Ciba (1941) US 2 267 257, CH-prior. 1937.
- 383 Ringold, H.J., et al. (1959) J. Am. Chem Soc. 81, 3712.
- 384 Searle (1959) US 2 891 079, US-prior. 1959.
- 385 Babcock, J.C., et al. (1958) J. Am. Chem. Soc. 80, 2904.
- 386 Ellis, B., et al. (1957) J. Chem. Soc. 4092.
- 387 Upjohn (1964) US 3 147 290, US-prior. 1956.
- 388 Syntex (1958) DE 1 097 986, MX-prior. 1956.
- 389 Hoechst (1977) US 4 024 248, DE-prior. 1974.
- 390 Dutta, A.S., et al. (1978) J. Med. Chem. 21, 1018.
- 391 Abbott (1977) US 3 914 412, US-prior. 1973.
- 392 Takeda (1976) GB 1 434 694, GB-prior. 1973.
- 393 Dutta, A.S., et al. (1978) J. Med. Chem. 21, 1018.
- 394 ICI/AstraZeneca (1977) US 4 100 274, GB-prior. 1976.
- 395 Coy, D.H., et al. (1976) J. Med. Chem. 19, 423.
- 396 Schally, A.V.and Coy, D.H. (1977) US 4 010 125, US-prior. 1975.
- 397 Debiopharm (1993) US 5 225 205, CH-prior. 1989. (Pamoate microparticles).
- 398 Rivier, J.E.F., et al. (1978) Life Sci. 23, 869.
- 399 Salk Institute (1981) US 4 244 946, US-prior. 1979.
- 400 Harper, M.J.K., et al. (1966) Nature 212, 87.
- 401 ICI (1985) US 4 536 516, GB-prior. 1962, 1965.
- 402 Farmos (1983) US 4 696 949, GB-prior. 1982.
- 403 ICI (1987) US 4 659 516, GB-prior. 1983.
- 404 Baker, J.W., et al. (1967) J. Med. Chem. 10, 93.
- 405 Schering Corpor. (1974) US 3 847 988, US-prior. 1971.
- 406 Roussel-Uclaf (1976) US 4 097 578, FR-prior. 1975.
- 407 Tucker, H., et al. (1988) J. Med. Chem. 31, 954.
- 408 ICI/AstraZeneca (1987) US 4 636 505, GB-prior. 1982.
- 409 Tran, Ch., et al. (2009) Science 324, 787.
- 410 Jung, M.E., et al. (2010) J. Med. Chem. 53, 2779.
- 411 Univ. California (04.05.2010) US 7 709 517, USA-prior. 13.05.2005.
- 412 Univ. California (22.05.2012) US 8 183 274, USA-prior. 13.05.2005.
- 413 Ciba (1958) US 2 848 455, CH-prior. 1955.
- 414 ICI/AstraZeneca (1990) US 4 935 437, GB-prior. 1987.
- 415 Ciba-Geigy/Novartis (1990) US 4 978 672, US-prior. 1986.
- 416 Farmitalia (1989) US 4 808 616, GB-prior. 1985.
- 417 Indiana Univ. (01.12.1998) US 5 843 901, US-prior. 07.06.1995.
- 418 Samant, M.P., et al. (2006) J. Med. Chem. 49, 3536.
- 419 Jiang, G., et al. (2001) J. Med. Chem. 44, 453.
- 420 Ferring (20.07.1999) US 5 925 730, US-prior. 11.04.1997.
- 421 Potter, G.A., et al. (1995) J. Med. Chem. 38, 2463.
- 422 Potter, G.A., et al. (1997) Org. Prep. Proced. Int. 29, 123.
- 423 British Technol. Group (18.02.1997) US 5 604 213, GB-prior. 31.03.1992.
- 424 Syntex (1988) US 4 753 935, US-prior. 1987.
- 425 Williams, R.H., et al. (1968) J. Antibiot. 21, 463.
- 426 Suzuki, S., et al. (1969) J. Antibiot. 22, 297.
- 427 ICI (1967) GB 1 157 099, GB-prior. 1966. (Fermentation).
- 428 Vézina, C., et al. (1975) J. Antibiot. 28, 721.
- 429 Sehgal, S.N., et al. (1975) J. Antibiot. 28, 727.
- 430 Ayerst (1975) US 3 929 992, US-prior. 1972.
- 431 Hoechst (1978) US 4 087 535, DE-prior. 1975.
- 432 Hoechst (1981) US 4 284 786, DE-prior. 1978.
- 433 Adachi, K., et al. (1995) Bioorg. Med. Chem. Lett. 5, 847, 853.
- 434 Kiuchi, M., et al. (2000) J. Med. Chem. 43, 2946.
- 435 Yoshitomi (18.02.1997) US 5 604 229, JP-prior. 21.10.1992, 20.07.1993.
- 436 Flanagan, M.E., et al. (2010), J. Med. Chem. 53, 8468–8484. (Synthesis).
- 437 Pfizer (04.09.2007) US 7 265 221, USA-prior. 10.12.1999.
- 438 Pfizer (28.09.2010) US RE 41783, USA-prior. 10.12.1999.
- 439 Pfizer (27.07.2007) US 7 301 023, USA-prior. 31.05.2001.
- 440 Rüegger, A., et al. (1976) Helv. Chim. Acta 59, 1075.
- 441 Sandoz (1978) US 4 117 118, CH-prior. 1974.
- 442 Kino, T., et al. (1987) J. Antibiot. 40, 1249.
- 443 Fujisawa (1986) EP 184 162, GB-prior. 1985.
- 444 Synthesis: Fujisawa (1990) EP 378 318, US-prior. 1989.
- 445 Folkman, J. (2007) Angiogenesis: an organizing principle for drug discovery?, Nature Rev. Drug Discovery 6, 273–286. – [Thalidomide, Lenalidomide, Pomalidomide].
- 446 Burroughs Wellcome (1962) US 3 056 785, US-prior. 1960.
- 447 Grünenthal (1957) GB 768 821, DE-prior. 1954.
- 448 Muller, G.W., et al. (1999) Bioorg. Med. Chem. Lett. 9, 1625.
- 449 Celgene (03.06.1997) US 5 635 517, US-prior. 24.07.1996.
- 450 Affil. Medical Res. (1974) US 3 839 346, US-prior. 1972.
- 451 Margolin, S.B. (25.09.2002) EP 702 551 US-prior. 07.05.1993, 19.05.1993.
- 452 Stewart, A.K., (2014) Science 343, 256.
- 453 Winter, G.E., et al. (2015) Science 348, 1376.
- 454 Celgene (03.06.1997) US 5 635 517, USA-prior. 24.07.1996.
