Synthesis and evaluation of novel fluorinated methotrexate derivatives for application to rheumatoid arthritis treatment

Journal of Medicinal Chemistry

Volumn 40, Issue 20, 1997, Pages 3280-3291

  Kokuryo, Yoshitsugu ^a   Kawata, Kyozo ^a   Nakatani, Takuji ^a   Kugimiya, Akira ^a   Tamura, Yoshinori ^a   Kawada, Kenji ^a   Matsumoto, Mitsunobu ^a   Suzuki, Ryuji ^a   Kuwabara, Kenji ^a   Hori, Yozo ^a   Ohtani, Mitsuaki ^a  

^a SHIONOGI AND CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CONCANAVALIN A; FLUORINE; GLUTAMIC ACID; IMMUNOSUPPRESSIVE AGENT; LIPOPOLYSACCHARIDE; METHOTREXATE DERIVATIVE; MITOGENIC AGENT;

ADJUVANT ARTHRITIS; ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIBODY PRODUCTION; ARTICLE; B LYMPHOCYTE; CONTROLLED STUDY; DIASTEREOISOMER; DRUG SYNTHESIS; FLUORINATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IMMUNOSUPPRESSIVE TREATMENT; MOUSE; NONHUMAN; RAT; RHEUMATOID ARTHRITIS; T LYMPHOCYTE;

ANIMALS; ANTIBODY FORMATION; ARTHRITIS, EXPERIMENTAL; ARTHRITIS, RHEUMATOID; B-LYMPHOCYTES; FEMALE; FLUORINE; FOLIC ACID ANTAGONISTS; METHOTREXATE; MICE; MODELS, CHEMICAL; RATS; RATS, INBRED LEW; STEREOISOMERISM; T-LYMPHOCYTES;

EID: 9844253897     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm970085n     Document Type: Article

References (48)

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7. Recently, antirheumatic MTX derivatives have been reported with a strategy similar to ours, see: (b) Matsuoka, H.; Kato, N.; Tsuji, K.; Maruyama, N; Suzuki, H.; Mihara, M.; Takeda, Y.; Yano, K. Antirheumatic agents. I: Novel methotrexate derivatives bearing an indoline moiety. Chem. Pharm. Bull. 1996, 44, 1332-1337. Matsuoka, H.; Maruyama, N; Suzuki, H.; Kuroki, T.; Tsuji, K.; Kato, N.; Ohi, N.; Mihara, M.; Takeda, Y.; Yano, K. Antirheumatic agents. II: Novel methotrexate derivatives bearing an alkyl-substituted benzene ring. Chem. Pharm., Bull. 1996, 44, 2287-2293. Matsuoka, H.; Ohi, N.; Mihara, M.; Suzuki, H.; Miyarnoto, K.; Maruyama, N; Tsuji, K.; Kato, N.; Akimoto, T.; Takeda, Y.; Yano, K.; Kuroki, T. Antirheumatic agents: Novel methotrexate derivatives bearing a benzoxazine or benzothiazine moiety. J. Med. Chem. 1997, 40, 105-111. (e) DeGraw, J. I.; Colwell, W. T.; Crase, J.; Smith, R. L.; Piper, J. R.; Waud, W. R.; Sirotnak, F. M. Analogues of methotrexate in rheumatoid arthritis. I: Effects of 10-deazaaminopterin analogues on type II collagen-induced arthritis in mice. J. Med. Chem. 1997, 40, 370-376. (f) Piper, J. R.; DeGraw, J. I.; Colwell, W. T.; Johnson, C. A.; Smith, R. L.; Waud, W. R.; Sirotnak, F. M. Analogues of methotrexate in rheumatoid arthritis. II: Effects of 5-deazaaminopterin, 5,10-deazaarninopterin, and analogues on type II collagen-induced arthritis in mice. J. Med. Chem. 1997, 40, 377-384.
8. Recently, antirheumatic MTX derivatives have been reported with a strategy similar to ours, see: (b) Matsuoka, H.; Kato, N.; Tsuji, K.; Maruyama, N; Suzuki, H.; Mihara, M.; Takeda, Y.; Yano, K. Antirheumatic agents. I: Novel methotrexate derivatives bearing an indoline moiety. Chem. Pharm. Bull. 1996, 44, 1332-1337. Matsuoka, H.; Maruyama, N; Suzuki, H.; Kuroki, T.; Tsuji, K.; Kato, N.; Ohi, N.; Mihara, M.; Takeda, Y.; Yano, K. Antirheumatic agents. II: Novel methotrexate derivatives bearing an alkyl-substituted benzene ring. Chem. Pharm., Bull. 1996, 44, 2287-2293. Matsuoka, H.; Ohi, N.; Mihara, M.; Suzuki, H.; Miyarnoto, K.; Maruyama, N; Tsuji, K.; Kato, N.; Akimoto, T.; Takeda, Y.; Yano, K.; Kuroki, T. Antirheumatic agents: Novel methotrexate derivatives bearing a benzoxazine or benzothiazine moiety. J. Med. Chem. 1997, 40, 105-111. (e) DeGraw, J. I.; Colwell, W. T.; Crase, J.; Smith, R. L.; Piper, J. R.; Waud, W. R.; Sirotnak, F. M. Analogues of methotrexate in rheumatoid arthritis. I: Effects of 10-deazaaminopterin analogues on type II collagen-induced arthritis in mice. J. Med. Chem. 1997, 40, 370-376. (f) Piper, J. R.; DeGraw, J. I.; Colwell, W. T.; Johnson, C. A.; Smith, R. L.; Waud, W. R.; Sirotnak, F. M. Analogues of methotrexate in rheumatoid arthritis. II: Effects of 5-deazaaminopterin, 5,10-deazaarninopterin, and analogues on type II collagen-induced arthritis in mice. J. Med. Chem. 1997, 40, 377-384.
9. Recently, antirheumatic MTX derivatives have been reported with a strategy similar to ours, see: (b) Matsuoka, H.; Kato, N.; Tsuji, K.; Maruyama, N; Suzuki, H.; Mihara, M.; Takeda, Y.; Yano, K. Antirheumatic agents. I: Novel methotrexate derivatives bearing an indoline moiety. Chem. Pharm. Bull. 1996, 44, 1332-1337. Matsuoka, H.; Maruyama, N; Suzuki, H.; Kuroki, T.; Tsuji, K.; Kato, N.; Ohi, N.; Mihara, M.; Takeda, Y.; Yano, K. Antirheumatic agents. II: Novel methotrexate derivatives bearing an alkyl-substituted benzene ring. Chem. Pharm., Bull. 1996, 44, 2287-2293. Matsuoka, H.; Ohi, N.; Mihara, M.; Suzuki, H.; Miyarnoto, K.; Maruyama, N; Tsuji, K.; Kato, N.; Akimoto, T.; Takeda, Y.; Yano, K.; Kuroki, T. Antirheumatic agents: Novel methotrexate derivatives bearing a benzoxazine or benzothiazine moiety. J. Med. Chem. 1997, 40, 105-111. (e) DeGraw, J. I.; Colwell, W. T.; Crase, J.; Smith, R. L.; Piper, J. R.; Waud, W. R.; Sirotnak, F. M. Analogues of methotrexate in rheumatoid arthritis. I: Effects of 10-deazaaminopterin analogues on type II collagen-induced arthritis in mice. J. Med. Chem. 1997, 40, 370-376. (f) Piper, J. R.; DeGraw, J. I.; Colwell, W. T.; Johnson, C. A.; Smith, R. L.; Waud, W. R.; Sirotnak, F. M. Analogues of methotrexate in rheumatoid arthritis. II: Effects of 5-deazaaminopterin, 5,10-deazaarninopterin, and analogues on type II collagen-induced arthritis in mice. J. Med. Chem. 1997, 40, 377-384.
10. Recently, antirheumatic MTX derivatives have been reported with a strategy similar to ours, see: (b) Matsuoka, H.; Kato, N.; Tsuji, K.; Maruyama, N; Suzuki, H.; Mihara, M.; Takeda, Y.; Yano, K. Antirheumatic agents. I: Novel methotrexate derivatives bearing an indoline moiety. Chem. Pharm. Bull. 1996, 44, 1332-1337. Matsuoka, H.; Maruyama, N; Suzuki, H.; Kuroki, T.; Tsuji, K.; Kato, N.; Ohi, N.; Mihara, M.; Takeda, Y.; Yano, K. Antirheumatic agents. II: Novel methotrexate derivatives bearing an alkyl-substituted benzene ring. Chem. Pharm., Bull. 1996, 44, 2287-2293. Matsuoka, H.; Ohi, N.; Mihara, M.; Suzuki, H.; Miyarnoto, K.; Maruyama, N; Tsuji, K.; Kato, N.; Akimoto, T.; Takeda, Y.; Yano, K.; Kuroki, T. Antirheumatic agents: Novel methotrexate derivatives bearing a benzoxazine or benzothiazine moiety. J. Med. Chem. 1997, 40, 105-111. (e) DeGraw, J. I.; Colwell, W. T.; Crase, J.; Smith, R. L.; Piper, J. R.; Waud, W. R.; Sirotnak, F. M. Analogues of methotrexate in rheumatoid arthritis. I: Effects of 10-deazaaminopterin analogues on type II collagen-induced arthritis in mice. J. Med. Chem. 1997, 40, 370-376. (f) Piper, J. R.; DeGraw, J. I.; Colwell, W. T.; Johnson, C. A.; Smith, R. L.; Waud, W. R.; Sirotnak, F. M. Analogues of methotrexate in rheumatoid arthritis. II: Effects of 5-deazaaminopterin, 5,10-deazaarninopterin, and analogues on type II collagen-induced arthritis in mice. J. Med. Chem. 1997, 40, 377-384.
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