Correction to: Discovery of the hemifumarate and (α- l -alanyloxy)methyl ether as prodrugs of an antirheumatic oxindole: prodrugs for the enolic OH group (Journal of Medicinal Chemistry (1996) 39 (10-18) DOI: 10.1021/jm950575k);Discovery of the hemifumarate and (α-L-alanyloxy)methyl ether as prodrugs of an antirheumatic oxindole: Prodrugs for the enolic OH group

Journal of Medicinal Chemistry

Volumn 39, Issue 1, 1996, Pages 10-18

  Robinson, Ralph P ^a   Reiter, Lawrence A ^a   Barth, Wayne E ^a   Campeta, Anthony M ^a   Cooper, Kelvin ^a   Cronin, Brian J ^a   Destito, Rosalina ^a   Donahue, Kathleen M ^a   Falkner, Fred C ^a   Fiese, Eugene F ^a   Johnson, Diane L ^a   Kuperman, Alexander V ^a   Liston, Theodore E ^a   Malloy, Deborah ^a   Martin, John J ^a   Mitchell, David Y ^a   Rusek, Frank W ^a   Shamblin, Sheri L ^a   Wright, Charles F ^a  

^a PFIZER INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

6 CHLORO 5 FLUORO 2,3 DIHYDRO 2 OXO 3 (2 THENOYL) 1 INDOLECARBOXAMIDE; 6 CHLORO 5 FLUORO 2,3 DIHYDRO 2 OXO 3 (2 THENOYL) 1 INDOLECARBOXAMIDE HEMIFUMARATE; ANTIRHEUMATIC AGENT; OXINDOLE DERIVATIVE; PRODRUG; TENIDAP; UNCLASSIFIED DRUG;

ARTHRITIS; ARTICLE; DRUG ACTIVITY; DRUG BIOAVAILABILITY; DRUG STABILITY;

EID: 13344261987     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.8b00306     Document Type: Erratum

References (42)

1. (a) Robinson, C. Tenidap sodium. Drugs Future 1990, 15, 898-901.
2. (b) Tenidap sodium, Enable, Enablex. Drugs Future 1993, 18, 875-878.
3. (a) Kraska, A. R.; Wilhelm, F. E.; Kirby, D. S.; Loose, L. D.; Ting, N.; Shanahan, W. R.; Weiner, E. S. Tenidap vs. piroxicam vs. piroxicam plus hydroxychloroquine in rheumatoid arthritis: a 24-week interim analysis. Arthritis Rheum. 1993, 36 (Suppl. 9), S57.
4. (b) Leeming, M. R. G. A double-blind randomized comparison of tenidap vs. auranofin plus diclofenac in early rheumatoid arthritis (RA). Arthritis Rheum. 1993, 36 (Suppl. 9), S111.
5. (a) Carty, T. J.; Showell, H. J.; Loose, L. D.; Kadin, S. B. Inhibition of both 5-lipoxygenase and cyclooxygenase pathways of arachidonic acid (AA) metabolism by CP-66,248, a novel anti-inflammatory compound. Arthritis Rheum. 1988, 31 (Suppl. 4), S89.
6. (b) Moilamen, E.; Alanko, J.; Asmawi, M. Z.; Vapaatalo, H. CP-66,248, a new anti-inflammatory agent is a potent inhibitor of leukotriene B4 and prostanoid synthesis in human polymorphonuclear leucocytes in vitro. Eicosanoids 1988, 1, 35-39.
7. (a) LaLiberte, R.; Perregaux, D.; Svensson, L.; Pazoles, C. J.; Gabel, C. A. Tenidap modulates cytoplasmic pH and inhibits anion transport in vitro. I. Mechanism and evidence of functional significance. J. Immunol. 1994, 153, 2180-2193.
8. (b) LaLiberte, R.; Perregaux, D.; Svensson, L.; Pazoles, C. J.; Gabel, C. A. Tenidap modulates cytoplasmic pH and inhibits anion transport in vitro. II. Inhibition of IL-1β production from ATP-treated monocytes and macrophages. J. Immunol., in press.
9. (c) McNiff, P. A.; LaLiberte, R.; Svensson, L.; Pazoles, C. J.; Gabel, C. A. Inhibition of cytokine activation processes in vitro by tenidap, a novel anti-inflammatory agent. Cytokine, in press.
10. (d) Otterness, I. G.; Bliven, M. L.; Downs, J. T.; Natoli, E. J.; Hanson, D. C. Inhibition of interleukin 1 synthesis by tenidap: a new drug for arthritis. Cytokine 1991, 3, 277.
11. (e) Sipe, J. D.; Bartle, L. M.; Loose, L. D. Modification of proinflammatory cytokine production by the antirheumatic agents tenidap and naproxen: a possible correlate with clinical acute phase response. J. Immunol. 1992, 148, 480.
12. Carty, T. J. Personal communication.
13. (a) Carty, T. J.; Marfat, A.; Moore, P. F.; Falkner, F. C.; Twomey, T. M.; Weissman, A Ampiroxicam, an anti-inflammatory agent which is a prodrug of piroxicam. Agents Actions 1993, 39, 157-165.
14. (b) Hopkins, S. J.; Rabasseda, X. Ampiroxicam: A prodrug of piroxicam devoid of gastrointestinal toxicity. Drugs Today 1994, 30, 557-563.
15. (c) Falkner, F. C.; Twomey, T. M.; Borger, A. P.; Garg, D.; Weidler, D.; Gerber, N.; Browder, I. W. Disposition of ampiroxicam, a prodrug of piroxicam, in man. Xenobiotica 1990, 20, 645-652.
16. (d) Ampiroxicam. Drugs Future 1992, 17, 451-454.
17. Marfat, A. Ether prodrugs of anti-inflammatory oxicams. US Patent 4,551,452.
18. (a) Farre, A. J.; Colombo, M.; Fort, A.; Gutiérrez, B.; Rodriguez, L.; Roser, R. Pharmacological properties of droxicam, a new nonsteroidal anti-inflammatory agent. Methods Find. Exp. Clin. Pharmacol. 1986, 8, 407-422.
19. (b) Esteve, A.; Farre, A. J.; Roser, R. Pharmacological profile of droxicam. Gen. Pharmacol. 1988, 19, 49-54.
20. (c) Esteve, A.; Martinez, L.; Roser, R.; Sagarra, R. Pharmacokinetics of droxicam in rat and dog. Methods Find. Exp. Clin. Pharmacol. 1986, 8, 423-429.
21. (a) Chérié-Lignière, G.; Montagnani, G.; Alberici, M.; Acerbi; D. Plasma and synovial fluid concentrations of piroxicam during prolonged treatment with piroxicam pivalic ester. Arzneim.-Forsch./Drug Res. 1987, 37, 560-563.
22. (b) Cinnoxicam, piroxicam cinnamate. Drugs Future 1991, 16, 164.
23. Prodrug reviews: (a) Bundgaard, H. Design of prodrugs: bio-reversible derivatives for various functional groups and chemical entities. In Design of Prodrugs; Bundgaard, H., Ed., Elsevier: Amsterdam, 1985; Chapter 1, pp 1-92. (b) Bundgaard, H. Novel chemical approaches in prodrug design. Drugs Future 1991, 16, 443-458. For a recent example of an enol prodrug, see: Burkhart, J. P.; Koehl, J. R.; Mehdi, S.; Durham, S. L.; Janusz, M. J.; Huber, E. W.; Angelastro, M. R.; Sunder, S.; Metz, W. A.; Shum, P. W.; Chen, T.-M.; Bey, P.; Cregge, R. J.; Peet, N. P. Inhibition of human neutrophil elastase. 3. An orally active enol acetate prodrug. J. Med. Chem. 1995, 38, 223-233.
24. Prodrug reviews: (a) Bundgaard, H. Design of prodrugs: bio-reversible derivatives for various functional groups and chemical entities. In Design of Prodrugs; Bundgaard, H., Ed., Elsevier: Amsterdam, 1985; Chapter 1, pp 1-92. (b) Bundgaard, H. Novel chemical approaches in prodrug design. Drugs Future 1991, 16, 443-458. For a recent example of an enol prodrug, see: Burkhart, J. P.; Koehl, J. R.; Mehdi, S.; Durham, S. L.; Janusz, M. J.; Huber, E. W.; Angelastro, M. R.; Sunder, S.; Metz, W. A.; Shum, P. W.; Chen, T.-M.; Bey, P.; Cregge, R. J.; Peet, N. P. Inhibition of human neutrophil elastase. 3. An orally active enol acetate prodrug. J. Med. Chem. 1995, 38, 223-233.
25. Prodrug reviews: (a) Bundgaard, H. Design of prodrugs: bio-reversible derivatives for various functional groups and chemical entities. In Design of Prodrugs; Bundgaard, H., Ed., Elsevier: Amsterdam, 1985; Chapter 1, pp 1-92. (b) Bundgaard, H. Novel chemical approaches in prodrug design. Drugs Future 1991, 16, 443-458. For a recent example of an enol prodrug, see: Burkhart, J. P.; Koehl, J. R.; Mehdi, S.; Durham, S. L.; Janusz, M. J.; Huber, E. W.; Angelastro, M. R.; Sunder, S.; Metz, W. A.; Shum, P. W.; Chen, T.-M.; Bey, P.; Cregge, R. J.; Peet, N. P. Inhibition of human neutrophil elastase. 3. An orally active enol acetate prodrug. J. Med. Chem. 1995, 38, 223-233.
26. 2O, DMSO, etc.) and could not be purified to a level acceptable for screening.
27. As a corollary, the hemisuccinate ester cannot be isolated after exposure of 1 to succinic anhydride.
28. Bundgaard, H.; Falch, E.; Jensen, E. A novel solution-stable, water-soluble prodrug type for drugs containing a hydroxyl or an NH-acidic group. J. Med. Chem. 1989, 32, 2503-2507.
29. Robinson, R. P.; Donahue, K. M. Synthesis of N-alkoxycarbonyl and N-carboxamide derivatives of anti-inflammatory oxindoles. J. Heterocycl. Chem. 1994, 1541-1544.
30. [(Aminoacyl)oxy]methyl esters have been examined as water-soluble prodrugs of cephalosporins; see: Wheeler, W. J.; Preston, D. A.; Wright, W. E.; Huffman, G. W.; Osborne, H. E.; Howard, D. P. Orally active esters of cephalosporin antibiotics. 3. Synthesis and biological properties of aminoacyloxymethyl esters of 7-[D-(-)-mandelamido]-3-[[(1-methyl-1H-tetrazol-5-yl)thio]-methyl]-3-cephem-4- carboxylic acid. J. Med. Chem. 1979, 22, 657-661.
31. This stability profile resembles that of cefamandole (aminoacyl)-oxy ester prodrugs (ref 15).
32. (a) Bundgaard, H.; Nielsen, N. M. Esters of N,N-disubstituted 2-hydroxyacetamides as a novel highly biolabile prodrug type for carboxylic acid agents. J. Med. Chem. 1987, 30, 451-454.
33. (b) Bundgaard, H.; Nielsen, N. M. Glycolamide esters as a novel biolabile prodrug type for nonsteroidal anti-inflammatory carboxylic acid drugs. Int. J. Pharm. 1988, 43, 101-110.
34. (c) Bundgaard, H.; Nielsen, N. M. Glycolamide esters as biolabile prodrugs of carboxylic acid agents: synthesis, stability, bioconversion, and physicochemical properties. J. Pharm. Sci. 1988, 77, 285-298.
35. 2, Table 1) were also prepared but were likewise poorly active as prodrugs of 1 in the rat.
36. Fujimoto, K.; Ishihara, S.; Yanagisawa, H.; Ide, J.; Nakayama, E.; Nakao, H.; Sugawara, S.-I.; Iwata, M. Studies on orally active cephalosporin esters. J. Antibiot. 1987, 40, 370-384.
37. Yoshimura, Y.; Hamagushi, N.; Yashiki, T. Preparation of 1-acyloxyethyl esters of 7-[2-(2-aminothiazol-4-yl)acetamido]-3-[[[1-(dimethylaminoethyl)-1H-tetrazol-5- yl]thio]methyl]ceph-3-em-4-carboxylic acid (cefotiam) and their oral absorption in mice. J. Antibiot. 1986, 39, 1329-1342.
38. The chloromethyl esters used for the preparation of compounds 5, 6, 17, 19, 20, and 22 are known in the literature. (a) Chloroethyl pivalate: Rasmussen, M.; Leonard, N. J. The synthesis of 3-(2′-deoxy-D-ribofuranosyl)adenine. Application of a new protecting group, pivaloyloxymethyl (Pom). J. Am. Chem. Soc. 1967, 89, 5439-5444. (b) Chloromethyl benzoate: Bodor, N.; Kaminski, J. J.; Worley, S. D.; Gerson, S. H. Quantitative evaluation of the reactivity of alkylating agents. Z. Naturforsch., B. Anorg. Chem. Org. Chem. 1980, 35, 758-763. (c) N-t-BOC-glycine chloromethyl ester, N-t-BOC-L-valine chloromethyl ester, and N-t-BOC-L-leucine chloromethyl ester: see ref 15.
39. The chloromethyl esters used for the preparation of compounds 5, 6, 17, 19, 20, and 22 are known in the literature. (a) Chloroethyl pivalate: Rasmussen, M.; Leonard, N. J. The synthesis of 3-(2′-deoxy-D-ribofuranosyl)adenine. Application of a new protecting group, pivaloyloxymethyl (Pom). J. Am. Chem. Soc. 1967, 89, 5439-5444. (b) Chloromethyl benzoate: Bodor, N.; Kaminski, J. J.; Worley, S. D.; Gerson, S. H. Quantitative evaluation of the reactivity of alkylating agents. Z. Naturforsch., B. Anorg. Chem. Org. Chem. 1980, 35, 758-763. (c) N-t-BOC-glycine chloromethyl ester, N-t-BOC-L-valine chloromethyl ester, and N-t-BOC-L-leucine chloromethyl ester: see ref 15.
40. The chloromethyl esters used for the preparation of compounds 5, 6, 17, 19, 20, and 22 are known in the literature. (a) Chloroethyl pivalate: Rasmussen, M.; Leonard, N. J. The synthesis of 3-(2′-deoxy-D-ribofuranosyl)adenine. Application of a new protecting group, pivaloyloxymethyl (Pom). J. Am. Chem. Soc. 1967, 89, 5439-5444. (b) Chloromethyl benzoate: Bodor, N.; Kaminski, J. J.; Worley, S. D.; Gerson, S. H. Quantitative evaluation of the reactivity of alkylating agents. Z. Naturforsch., B. Anorg. Chem. Org. Chem. 1980, 35, 758-763. (c) N-t-BOC-glycine chloromethyl ester, N-t-BOC-L-valine chloromethyl ester, and N-t-BOC-L-leucine chloromethyl ester: see ref 15.
41. Lutz, R. E. The synthesis and configurations of unsaturated 1,4-diketones and ketonic acids, and the stereochemical mechanism of the addition of bromine. Studies on unsaturated 1,4-diketones. VI. J. Am. Chem. Soc. 1930, 52, 3423.
42. Sharma, S. K.; Miller, M. J.; Payne, S. M. Spermexatin and spermexatol: new spermidine-based siderophore analogues. J. Med. Chem. 1989, 32, 357-367.