From chiral bromo[13,14Cn]acetyl sultams to complex molecules singly/multiply labelled with isotopic carbon

Journal of Labelled Compounds and Radiopharmaceuticals

Volumn 45, Issue 10, 2002, Pages 867-897

  Voges, R ^a  

^a NOVARTIS PHARMA AG   (Switzerland)

Author keywords

C 14 labelled BABS; Chiral bromo 13,14Cn acetyl sultams; Chiral synthons; DPMGBS; e.p. C 14 labelled drug substances; PABS; Stereoselective syntheses

Indexed keywords

ADDITION REACTIONS; AMINO ACIDS; CARBON; CARBOXYLIC ACIDS; KETONES; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

C-14 LABELED BABS; CHIRAL BROMO[13,14CN]ACETYL SULTAM; CHIRAL SYNTHONS; DPMGBS; DRUG SUBSTANCES; EP C-14 LABELED DRUG SUBSTANCE; N ACETYLS; PABS; STEREOSELECTIVE SYNTHESIS; SULTAMS;

ALDEHYDES;

2 BROMO 3 HYDROXYCARBOXYLIC ACID C 13; 2 BROMO 3 HYDROXYCARBOXYLIC ACID C 14; 2 HYDROXYACID; ALDEHYDE; BROMOACETYLBORNANE 10,2 SULTAM C 13; BROMOACETYLBORNANE 10,2 SULTAM C 14; CARBON 13; CARBON 14; CARBOXYLIC ACID DERIVATIVE; CYCLOSPORIN DERIVATIVE; DIETHYLPHOSPHONOACETYLBORNANE 10,2 SULTAM C 13; DIETHYLPHOSPHONOACETYLBORNANE 10,2 SULTAM C 14; DIPHENYLMETHYLENEGLYCINYLBORNANE 10,2 SULTAM C 13; DIPHENYLMETHYLENEGLYCINYLBORNANE 10,2 SULTAM C 14; ESTER; EVEROLIMUS; HYDROXYACID; ISOTHIOCYANATOACETYLBORNANE 10,2 SULTAM C 13; ISOTHIOCYANATOACETYLBORNANE 10,2 SULTAM C 14; LIPID X; NVP IMM 125; NVP NIM 811; PACLITAXEL; RADIOPHARMACEUTICAL AGENT; SDZ ISQ 844; SDZ PR 105; TITANIUM DERIVATIVE; TRICHLOROTITANIUM ENOLATE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VALSARTAN; VALSPODAR;

CHEMICAL REACTION; CHIRALITY; DIASTEREOISOMER; DRUG PURIFICATION; DRUG PURITY; ENANTIOMER; ISOTOPE LABELING; REVIEW; STEREOCHEMISTRY; SYNTHESIS; TECHNIQUE;

EID: 0036734984     PISSN: 03624803     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlcr.610     Document Type: Review

References (104)

1. Voges R. Stereoselective procedures in the synthesis of e.p. isotopically labelled compounds. In Synthesis and Applications of Isotopically Labelled Compounds, Allen J, Voges R (eds). Wiley: Chichester, 1995; 1-26.
2. (a) Rodriguez I, Voges R. J Label Compd Radiopharm 2000; 43: 169-176;
3. (b) Oppolzer W, Zhou G. Thesis, Universite de Geneve 1993;
4. (c) Voges R, Appenzeller U. Internal Report, Sandoz Pharma AG, Basel, 1993, unpublished.
5. (a) Pridgen LN, Abdel-Magid AF, Egglestone DS, Lantos I, Shilcrat S. J Org Chem 1993; 58: 5107-5118;
6. (b) Pridgen LN, Abdel-Magid A, Lantos I, Tetrahedron Lett 1989; 30: 5539-5542;
7. (c) Abdel-Magid AF, Pridgen LN, Egglestone DS, Lantos I. J Am Chem Soc 1986; 108: 4595-4602;
8. (d) Pridgen LN, Abdel-Magid A, Lantos I, Tetrahedron Lett 1984; 25: 3273-3276.
9. Voges R, Metz Y, Internal Report, Sandoz Pharma AG, Bourd, 1995, unpublished.
10. (a) Burtscher P, Kohler B, Metz Y, Voges R, Wenger R. J Label Compd Radiopharm 2000; 43: 205-216;
11. (b) Moenius Th, Voges R, Mahnke M, Burtscher P, Metz Y, Guenat Ch. J Label Compd Radiopharm 1999; 42: 29-41;
12. 15N]amino acids. In. Synthesis and Applications of Isotopically Labelled Compounds, Allen J, Voges R (eds). Wiley: Chichester, 1995, 761-766.
13. (a) Evans DA, Weber AE. J Am Chem Soc 1987; 109: 7151-7157;
14. (b) Evans DA, Weber AE. J Am Chem Soc 1986; 108: 6757-6761;
15. (c) Voges R, Metz Y. Internal Report, Sandoz Pharma AG, Basel, 1993, unpublished.
16. (a) Oppolzer W. Pure Appl Chem 1990; 62: 1241-1250;
17. (b) Oppolzer W. Pure Appl Chem 1988; 60: 39-48;
18. (c) Oppolzer W. Tetrahedron 1987; 43: 1969-2004.
19. (a) Rossiter BE, Swingle NM. Chem Rev 1992; 92: 771-806;
20. (b) Oppolzer W, Poli G. Tetrahedron Lett 1986; 27: 4717-4720;
21. (c) Oppolzer W, Poli G. Tetrahedron 1986; 45: 479-486;
22. (d) Oppolzer W, Klingma AJ. Helv Chim Acta 1989; 72:1337-1349;
23. (e) Oppolzer W, Poli G, Kingma AJ, Starkemann C, Bernardinelli G. Helv Chim Acta 1987; 70: 2201-2214;
24. (f) Oppolzer W, Tamura O, Deerberg J. Helv Chim Acta 1992; 75: 1965-1978;
25. (g) Oppolzer W, Arend AJ, Poli G. Tetrahedron 1989; 45: 479-488;
26. (h) Oppolzer W, Schneider P. Helv Chim Acta 1986; 69: 1817-1823;
27. (i) Oppolzer W, Moretti R, Bernardinelli G. Tetrahedron Lett 1986; 27: 4713-4716;
28. (j) Oppolzer W, Mills RJ, Pachinger W, Stevenson T. Helv Chim Acta 1986; 69: 1542-1548;
29. (k) Oppolzer W, Poli G, Starkemann C, Bernardinell G. Tetrahedron Lett 1988; 29: 3559-3564.
30. (a) Kim BH, Curran DP. Tetrahedron 1993; 49: 293-318;
31. (b) Oppolzer W, Dupuis D, Poli G, Raynham TM, Bernardinelli G. Tetrahedron 1988; 46: 5885-5888;
32. (c) Vandewalle M, van der Eycken J, Oppozer W, Vulluid C. Tetrahedron 1986; 42: 4035-4043;
33. (d) Oppolzer W, Dupuis D. Tetrahedron 1985; 44: 5437-5440;
34. (e) Oppolzer W, Dupuis D. Tetrahedron Lett 1985; 26, 5437-5440;
35. (f) Oppolzer W, Chapuis C, Bernardinelli G. Helv Chim Acta 1984; 67: 1397-1401;
36. (g) Curran DP, Heffner TA. J Org Chem; 1990; 55: 4585-4595;
37. (h) Curran DP, Kim BH, Daugherty J, Heffner TA. Tetrahedron Lett 1988; 29: 3555-3563;
38. (i) Lee AWM, Yuen WH, Xia PF, Wong WY. Tetrahedron: Asymmetry 1999; 10: 1421-1424;
39. (j) Oppolzer W, Barras JP. Helv Chim Acta 1987; 70: 1666-1674.
40. (a) Reetz MT. Angew Chem 1991; 103: 1559-1573;
41. (b) Reetz MT, Lauterbach EH. Tetrahedron Lett 1991; 32: 4477-4480;
42. Valverde S, Martin-Lomas M, Herradon B, Garcia-Ochoa S. Tetrahedron 1987; 43: 1895-1901;
43. Minami N, Ko SS, Kishi Y. J Am Chem Soc 1982; 104: 1109-1111.
44. (a) Voges R, Appenzeller U, Eustache J, Metz Y Internal Report, Sandoz Pharma AG, Basel, 1993, unpublished;
45. (b) Voges R, Metz Y. Internal Report, Sandoz Pharma AG, Basel, 1987, unpublished;
46. (c) Macher I, Unger FM. Internal Report, Sandoz Forschungsinstitut, Vienna, 1987, unpublished;
47. (d) Inage M, Chaki H, Imoto M, Shimemoto T, Kusumoto S, Shiba T. Tetrahedron Lett 1983; 24: 2011-2014.
48. Iversen T, Bundle D. J Chem Soc Chem Comm 1981; 1240-1241.
49. (a) Wenger R. Helv Chim Acta 1983; 66: 502-525;
50. (b) Wenger R. Angew Chem 1985; 97: 88-96;
51. (c) Rich HD, Colucci WJ, Teng RD, Petri JA. J Org Chem 1990; 55: 2895-2903;
52. (d) Wasmuth D. Internal Report, Sandoz Pharma AG, Basel, 1990, unpublished.
53. (a) Rowinsky EK. Semin Oncol 1997; 24 (6, Suppl. 19): 1;
54. (b) Goldspiel BR. Pharmacotherapy 1997; 17 (5, Part 2): 1102-1127;
55. (c) Lam F, Chan J, Kuhn JG. J Oncol Pharm Pract 1997; 3: 76-93.
56. (a) Brown S, Jordan AM, Lawrence NJ, Prichard RG, McGown AT. Tetrahedron Lett 1998; 39: 3559-3562;
57. (b) Sharpless KB, Li G, Chang HT. Patent Application WO97-US8593 970521;
58. (c) Gennar C, Carcano M, Donghi M, Mongelli N, Vanotti E, Vulpetti A. J Org Chem 1997; 62: 4746-4755;
59. (d) Boa AN, Jenkins PR, Lawrence NJ. Contemp Org Synth 1994; 1: 47-75;
60. (e) Chong JM, Sharpless KB, J. Org Chem. 1985; 50, 1560-1563;
61. (f) Commercon A, Bezard D, Bernard F, Bourzat JD. Tetrahedron Lett 1992; 33: 5185-5188;
62. (g) Gou DM, Liu YC, Chen CS. J Org Chem 1993; 58: 1287-1289.
63. (a) Ojima I, Sun CM, Zucco M, Park YH, Duclos O, Kuduk S. Tetrahedron Lett 1993; 34: 4149-4152;
64. (b) Walter DG, Swigor JE, Kant J, Schroeder DR. J Label Compd Radiopharm 1994; 34: 973-980.
65. (a) Williams RM. Synthesis of Optically Active a-Amino Acids, Pergamon Press: Oxford, 1989; 1-97;
66. (b) Seebach D, Juarist E, Miller DD, Schickly C, Weber T. Helv Chim Acta 1987; 70: 237-261.
67. Bollinger P, Bölsterli JL, Borel JF, Krieger M, Payne TG, Traber RP, Wenger R, E.P. 0296 122 (1988).
68. Moenius Th, Voges R, Burtscher P, Zueger Ch. J Label Compd Radiopharm 2000; 43: 1245-1252.
69. (a) Boyle MJ, Kahans BD. In Immunosuppressive Drugs, Thomson AV, Starzl TE (eds). Edward Arnold: London, 1994; 129-143;
70. Schuurman HJ, Cottens S, Fuch S, et al. Transplantation 1997; 64: 36-42.
71. (a) Roberts MF, Demain AL, Paiva NL. Enzyme Microb Technol 1993; 15: 581-588;
72. (b) Lowden P, B6hm G, Staunton J, Leadley P. Angew Chem 1996; 108: 2395-2397.
73. Josien H, Martin A, Chassaing G. Tetrahedron Lett 1991; 32: 6547-6550.
74. (a) Myers AG. US Patent 1998; No. 5,760,237;
75. (b) Myers AG, Gleason JL, Yoon T, Kung DW. J Am Chem Soc 1997; 119: 656-673;
76. (c) Myers AG, Gleason JL. J Org Chem 1996; 61: 813-815;
77. (d) Myers AG, Yoon T, Gleason JL. Tetrahedron Lett 1995; 36: 4555-4558;
78. (e) Myers AG, Yoon T, Gleason JL. Tetrahedron Lett 1995; 36: 9429-9432.
79. (a) Metternich R, Powling M, Taparelli C, Cook N. Internal Report, Sandoz Pharma AG, Basel, 1991, unpublished;
80. 14C]-Ala]NVP MTH958. In Synthesis and Applications of Isotopically Labelled Compounds, Pleiss U, Voges R (eds), vol. 7. Wiley: Chichester, 2001; 295-299;
81. (c) Bowler KS, Internal Report, Amersham Life Science, 1996, unpublished.
82. Oppolzer W, Mills RJ, Reglier M. Tetrahedron Lett 1986; 27: 183-186.
83. Voges R, Naef R, Metz Y, Internal Report Sandoz Pharma AG, Basel, 1992, unpublished.
84. (a) Oppolzer W, Moretti R. Helv Chim Acta 1986; 69: 1923-1928;
85. (a) Oppolzer W, Moretti R. Tetrahedron 1988; 44: 5541-5548.
86. (a) Rodriguez I, Metz Y, Voges R. J Label Compd Radiopharm 2001; 44: 963-964;
87. (b) Voges R, Metz Y. C-14 Labelling of NVP BPI562, a β-Amino Acid Derivative. In Synthesis and Applications of Isotopically Labelled Compounds, Pleiss U, Voges R (eds), vol. 7. Wiley: Chichester, 2001; 307-310;
88. (c) Evans DA, Wu LD, Wiener LLM, Johnson JS, Ripin DHB, Tedrow JS. J Org Chem 1999; 64: 6411-6417;
89. (d) Sibi MS, Deshpande PK. J Chem Soc Perkin Trans I, 2000; 1461-1466;
90. (e) Sibi MP. Aldrichim Acta 1999; 35: 93-107;
91. (f) Rodriguez I, Kohler B, Metz Y, Voges R. Novartis Pharma AG, Basel, 2001, unpublished results.
92. (a) Arvidson PI, Frackenpohl J, Schreiber JV, Seebach D. Project Report 2000, ETH Zürich, unpublished results;
93. (b) Abele S, Seebach D. Eur J Org Chem 2000; 65: 1-15
94. (c) Abele S, Seebach D. Helv Chim Acta 1999; 82: 1774-1783.
95. Harding JR, Hughes RS, Kelly NM, Sutherland A, Willis CL. J Chem Soc Perkin Trans 1 2000; 3406-3416.
96. Voges R, Kohler B. Internal Report, Sandoz Pharma AG, Basel, 1993; unpublished results.
97. (a) Corey EJ, Huang HC. Tetrahedron Lett 1989; 30: 5235-5238;
98. (b) Ireland RE, Highsmith Th, Gegnas LD, Gleason JL. J Org Chem 1992; 57: 5071-5073.
99. Thom C, Kocienski P, Sarowicki K, Synthesis 1993; 475-477.
100. (a) Sedrani R, Stone G. Internal Report, Novartis Pharma AG, Basel, 1996, unpublished;
101. (b) Schuler W, Sedrani R, Cottens S, Häberlin B, Schulz M, Schuurmann HL, Zenke G, Zerwes HG, Schreier M. Transplantation 1997; 64: 36-42.
102. Dannecker R, Hauck Ch. NVP RAD001, Human in vitro Biotransformation: LC-MS Investigation of Metabolites, Internal Report, Novartis Pharma AG, Basel, 1997, unpublished results.
103. (a) Billich A, Gstach H, Rosenworth, B. Internal Report, Sandoz Forschungsinstitut, Vienna, 1993, unpublished
104. (b) Voges R, Gstach H, Metz Y. Internal Report, Sandoz Pharma AG, Basel, 1993, unpublished results.