Antirheumatic agents: Novel methotrexate derivatives bearing a benzoxazine or benzothiazine moiety

Journal of Medicinal Chemistry

Volumn 40, Issue 1, 1997, Pages 105-111

  Matsuoka, Hiroharu ^a   Ohi, Nobuhiro ^a   Mihara, Masahiko ^a   Suzuki, Hiroshi ^a   Miyamoto, Katsuhito ^a   Maruyama, Noriaki ^a   Tsuji, Keiichiro ^a   Kato, Nobuaki ^a   Akimoto, Toshio ^a   Takeda, Yasuhisa ^a   Yano, Keiichi ^a   Kuroki, Toshio ^a  

^a CHUGAI PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIRHEUMATIC AGENT; METHOTREXATE DERIVATIVE; N [[4 [(2,4 DIAMINO 6 PTERIDINYL)METHYL] 3,4 DIHYDRO 2H 1,4 BENZOTHIAZIN 7 YL]CARBONYL]HOMOGLUTAMIC ACID; N [[4 [(2,4 DIAMINOPTERIDIN 6 YL)METHYL] 3,4 DIHYDRO 2H 1,4 BENZOTHIAZIN 7 YL]CARBONYL]GLUTAMIC ACID; N [[4 [(2,4 DIAMINOPTERIDIN 6 YL)METHYL] 3,4 DIHYDRO 2H 1,4 BENZOTHIAZIN 7 YL]CARBONYL]HOMOGLUTAMIC ACID; N [[4 [(2,4 DIAMINOPTERIDIN 6 YL)METHYL] 3,4 DIHYDRO 2H 1,4 BENZOXAZIN 7 YL]CARBONYL]HOMOGLUTAMIC ACID; UNCLASSIFIED DRUG;

ADJUVANT ARTHRITIS; ANIMAL MODEL; ARTICLE; CELL PROLIFERATION; CONTROLLED STUDY; DOSE RESPONSE; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; MALE; MONONUCLEAR CELL; NONHUMAN; RAT; RHEUMATOID ARTHRITIS; SYNOVIOCYTE;

ANIMALS; ANTIRHEUMATIC AGENTS; ARTHRITIS, EXPERIMENTAL; CELL DIVISION; HUMANS; MALE; METHOTREXATE; MONOCYTES; OXAZINES; RATS; SYNOVIAL FLUID; THIAZINES;

EID: 8044234375     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9605288     Document Type: Article

References (19)

1. Gubner, R.; August, S.; Ginsberg, V. Therapeutic Suppression of Tissue Reactivity. II. Effect of Aminopterine in Rheumatoid Arthritis. Am. J. Med. Sci. 1951, 221, 176-182.
2. Weinstein, G. D. Methotrexate. Diagnosis and Treatment. Ann. Intern. Med. 1977, 86, 199-204.
3. Owen, E. T.; Cohen, M. L. Methotrexate in Reiter's Disease. Ann. Rheum. Dis. 1979, 38, 48-50.
4. Sokoloff, M. C.; Goldberg, L. S.; Pearson, C. M. Treatment of Corticosteroid Resistant Polymyositis with Methotrexate. Lancet 1971, 1, 14-16.
5. Williams, H. J.; Willkens, R. F.; Samuelson, C. O.; Alarcon, G. S.; Guttadauria, M.; Yarboro, C.; Polisson, R. P.; Weiner, S. R.; Luggen, M. E.; Billingsley, L. M.; Dahl, S. L.; Egger, M. J.; Reading, J. C.; Ward, J. R. Comparison of Low-dose Oral Pulse Methotrexate and Placebo in the Treatment of Rheumatoid Arthritis. Arthritis Rheum. 1985, 28, 721-730.
6. Hamdy, H.; McKendry, R. J. R.; Mierins, E.; Liver, J. A. Low-dose Methotrexate Compared with Azathioprine in the Treatment of Rheumatoid Arthritis. Arthritis Rheum. 1987, 30, 361-368.
7. Weinblatt, M. E.; Weissman, B. N.; Holdsworth, D. E.; Fraser, P. A.; Maier, A. L.; Falchuk, K. R.; Coblyn, J. S. Long-term Prospective Study of Methotrexate in the Treatment of Rheumatoid Arthritis. Arthritis Rheum. 1992, 35, 129-145.
8. Furst, D. E.; Erikson, N.; Clute, L.; Koehnke, R.; Burmeister, L. F.; Kohler, J. A. Adverse Experience with Methotrexate During 176 Weeks of a Longterm Prospective Trial in Patients with Rheumatoid Arthritis. J. Rheumatol. 1990, 17, 1628-1635.
9. Galivan, J. Evidence for the Cytotoxic Activity of Polyglutamate Derivatives of Methotrexate. Mol. Pharmacol. 1980, 17, 105-110.
10. Chabner, B. A.; Allegra, C. J.; Curt, G. A.; Clendeninn, N. J.; Baram, J.; Koizumi, S. Polyglutamation of Methotrexate. J. Clin. Invest. 1985, 76, 907-912.
11. Matsuoka, H.; Kato, N.; Tsuji, K.; Maruyama, N.; Suzuki, H.; Mihara, M.; Takeda, Y.; Yano, K. Antirheumatic Agents. 1. Novel Methotrexate Derivatives Bearing an Indoline Moiety. Chem. Pharm. Bull. 1996, 44, 1332-1337.
12. Oefner, C.; D'Arcy, A.; Winkler, F. K. Crystal Structure of Human Dihydrofolate Reductase Complexed with Folate. Eur. J. Biochem. 1988, 174, 377-385.
13. Akimoto, T.; Matsuoka, H.; Suzuki, H.; Kato, N.; Tsuji, K.; Kuroki, T.; Ohi, N.; Maruyama, N.; Mihara, M.; Takeda, Y. The Docking Studies of Novel Antirheumatic Agent to Dihydrofolate Reductase. Pharmaceutical Soc. Jpn. 11th Annual Meeting Abstract, 1996; 27 (L2) 11-2.
14. Wolfe, J. F. Step-growth Propagation of High Molecular Weight Rigid Rod Poymers. SRI International Technical Report, AFOSFRTR-80-1370, Order No. AD-A093879, 1980.
15. Piper, J. R.; McCaleb, G. S.; Montgomery, J. A.; Kisliuk, R. L.; Gaumont, Y.; Sirotnak, F. M. 10-Propagylaminopterine and Alkyl Homologues of Methotrexate as Inhibitors of Folate Metabolism. J. Med. Chem. 1982, 25, 877-880.
16. Piper, J. R.; Montgomery, J. A. Preparation of 6-(Bromomethyl)-2,4-Pteridinediamine Hydrobromide and Its Use in Improved Synthesis of Methotrexate and Related Compound. J. Org. Chem. 1977, 42, 208-211.
17. Moran, R. G.; Colman, P. D.; Rosowsky, A.; Forsch, R. A.; Chan, K. K. Structural Features of 4-Amino Antifolates Required for Substrate Activity with Manmalian Folylpolyglutamate Synthetase. Mol. Pharmacol. 1984, 27, 156-166.
18. Mihara, M.; Ikuta, M.; Koishihara, Y.; Ohsugu, Y. Interleukin 6 Inhibits Delayed-type Hypersensitivity and the Developmant of Adjuvant Arthritis. Eur. J. Immunol. 1991, 21, 2327-2331.
19. Trentham, D. E.; Townes, A. S.; Kang, A. H. Autoimmunity to Type II Collagen: an Experimental Model of Arthritis. J. Exp. Med. 1977, 146, 867-868.