Immunosuppressive compounds and methods

A compound and pharmaceutical technology, applied in the field of immunosuppressive compounds and can solve the problems of complex suspensions

Inactive Publication Date: 2000-03-01
法玛吉尼西斯公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Suspensions are more complex than solutions in terms of dosing standards

Method used

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  • Immunosuppressive compounds and methods

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0141] Triptolide Succinate (YM-262)

[0142] A solution of triptolide (100 mg) in 10 ml pyridine was treated with succinic anhydride (150 mg) at room temperature. The reaction was carried out at 85°C for 30 hours under nitrogen atmosphere. Hexane (50ml) was added to the resulting mixture to precipitate a crude product which was collected by filtration and washed with hexane. Recrystallization from ether / hexane gave 90 mg (70%) of triptolide succinate (YM-262), m.p.: 111-113°C.

[0143] IR(KBr): 3431.8, 2974.6, 1375.5, 1743.8, 1159.4, 1022.4 cm -1 . 1 HNMR (CDCl 3 ): 5.08 (1H, s, 14-CH), 4.67 (2H, s, 19-CH2), 3.82 (1H, d, 11-CH), 3.50 (1H, d, 12-CH), 3.43 (1H, d, 7-CH), 2.75 (5H, m, CH2CH2, 5-CH), 2.30 (1H, d-m, 15-CH), 2.15 (2H, m, 6-CH a , 2-CH a ), 1.88 (2H, m, 2-CH b ,6-CH b B), 1.55 (1H, m, 1-CH b ), 1.20 (1H, m, 1-CH 2 ), 1.05(3H, s, 20-CH3), 0.95(3H, d, 16-CH 3 ), 0.83 (3H, d, 17-CH 3 )ppm. MS (m / z): 461 (M+1).

Embodiment 2

[0145] Triptolide succinate trisalt (YM-273)

[0146] A solution of triptolide succinate (20 mg) and tris(hydroxymethyl)aminomethane (5.3 mg) in 20 ml of water was mixed and stirred for 1 hour. The solution was filtered and the filtrate was lyophilized to give 24 mg (96%) of a white powder.

[0147] IR(KBr): 3391, 2937.96, 1745.80, 1562.9, 1411.67, 1159, 1066.57, 1024.57cm -1 . 1 H NMR (D 6 -DMSO, ppm): 5.00 (1H, s, 14-CH), 4.85 (2H, d, 19-CH2), 3.95 (1H, d, 11-CH), 3.70 (1H, d, 12-CH), 3.55 (1H, d, 7-CH), 3.30 (6H, s, 3CH 2 O), 2.65 (1H, m, 5H), 2.45 (2H, m, CH2), 2.20 (3H, m, CH 2 , 15-CH), 1.90 (4H, m, 6-CH 2 , 2-CH2), 1.34 (2H, br, 1-CH2), 0.95 (3H, s, 20-CH3), 0.88 (3H, d, 16-CH3), 0.75 (3H, d, 17-CH 3 ).

Embodiment 3

[0149] Triptolide Sodium Succinate (YM-274)

[0150] A solution of triptolide succinate (20 mg) and sodium bicarbonate (3.65 mg) in 20 ml of water was mixed and stirred for 30 minutes. The aqueous solution was filtered and the filtrate was lyophilized to give 20 mg (95%) of a white powder.

[0151] IR(KBr): 3431.8, 2975.56, 1743.87, 1577.97, 1419.79, 1163.22, 1022.40cm -1 . 1 H NMR (D 6 -DMSO, ppm): 5.00 (1H, s, 14-CH), 4.85 (2H, d, 19-CH2), 3.95 (1H, d, 11-CH), 3.70 (1H, d, 12-CH), 3.55 (1H, d, 7-CH), 2.58 (1H, m, 5H), 2.45 (2H, m, CH2), 2.20 (3H, m, CH2, 15-CH), 1.90 (4H, m, 6- CH2, 2-CH2), 1.34 (2H, br, 1-CH2), 0.95 (3H, s, 20-CH3), 0.88 (3H, d, 16-CH3), 0.75 (3H, d, 17-CH3) .

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Abstract

Compounds and methods for use in immunosuppressive and anti-inflammatory treatment are described. The compounds are triptolide analogs with improved water solubility and low toxicity.

Description

field of invention [0001] The present invention relates to compounds and methods for immunosuppressive and anti-inflammatory therapy, and reduction of male fertility. [0002] References [0003] Bradley, L., SELECTED METHODS INCELLULAR IMMUNOLOGY, W.H. Freeman and Company, San Francisco, pp. 162-164, (1980) [0004] Briggs, J, D., Immunol. Lett. 29(1-2):89-94 (1991) [0005] Hasan, R. et al., Transplantation 54:408 (1992) [0006] Kennedy, M.S. et al., Am. J. Med. 78:978 (1983) [0007] Keown, P.A., Clin. Transplants 205-223 (1991) [0008] Kocienski, P.J., Protecting Groups, Georg Thieme Verlag, Stuttgart (1994) [0009] Kupchan, S.M. et al., J. Am. Chem. Soc. 94:719 (1972) [0010] Kupchan, S.M. et al., U.S. Patent No. 4,005,108 (1977) [0011] Lipsky, P.E. et al., U.S. Patent No. 5,294,443 (1994) [0012] Ma, P-C. et al., J. Chin Pharm. Sci. 1:12 (1992) [0013] Mishell, B. et al., eds., SELECTED METHODS IN CELLULAR IMMUNOLOGY, W.H. Freeman and Co., San Francisco,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/22A61K31/34A61K31/365A61P11/06A61P15/16A61P29/00A61P37/06C07D307/77
CPCC07D307/77A61P11/06A61P15/16A61P29/00A61P37/06
Inventor 齐友矛约翰·H·马瑟约翰·M·菲德勒
Owner 法玛吉尼西斯公司
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