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Steroid compound containing nitrogen and its preparation method

A technology of steroidal compounds and compounds, which is applied in the field of glucocorticoid nitrogen-containing steroidal compounds and their preparation, and the intermediates for the preparation of these compounds, and can solve problems such as not much progress in research

Inactive Publication Date: 2003-04-30
NANKAI UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, research in this area has not made much progress

Method used

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  • Steroid compound containing nitrogen and its preparation method

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Experimental program
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Effect test

Embodiment 1

[0027] Preparation of 11β,17α,21-trihydroxy-pregn-4-ene-3,20-dione-21-methanesulfonate

[0028] 11β, 17α, 21-trihydroxy-pregn-4-ene-3,20-dione (hydrocortisone, 30g; 82.77mmol), pyridine (160ml) in a 250ml three-necked flask, cooled to 0°C, To this was added methanesulfonyl chloride (15.5ml, 191.64mmol) dropwise over half an hour. React at 0-5°C for 3 hours. After the reaction, pour the reaction solution into 2000ml of ice water, let it stand for more than 2 hours, filter with suction, wash with water, and dry to obtain 33.53g of crude product with a yield of 91.95%.

[0029] The obtained crude product was recrystallized from a mixed solvent of chloroform / methanol to obtain 30.5 g of pure product. Mp178~180(dec.)℃.

[0030] Elemental Analysis: C 22 h 32 o 7 S, Cal.C59.98%, H7.32%; Found: 59.88%, H7.50%

[0031] 1 HNMR (δ, 200MHz, DMSO-d6): 5.55(1H, s), 5.49(1H, s), 5.28(1H, d, J AB 17.6Hz), 4.87 (1H, d, J AB 17.6Hz), 4.35(1H, d, J3.1Hz), 4.25(1H, s), 3.23(3H, s), 1.35(...

Embodiment 2

[0033] Preparation of 11β, 17α, 21-trihydroxy-pregna-1,4-ene-3,20-dione-21-methanesulfonate

[0034]11β, 17α, 21-trihydroxy-pregna-1,4-en-3,20-one (prednisolone, 50.33g, 139.63mmol), tetrahydrofuran (500ml), triethylamine (46.70ml, 335.11mmol ) in a 1000ml three-neck flask, stirred mechanically, added methanesulfonyl chloride (25.5ml, 329.46mmol) dropwise at below 0°C within 0.5 hours, and reacted at 0-5°C for 3 hours. After the reaction, the reaction solution was extracted with 1000ml of ethyl acetate, washed with 300ml×3 water, the organic phase was taken, dried over anhydrous sodium sulfate, and then concentrated to dryness under reduced pressure to obtain 58.2g of crude product with a yield of 95.04%. Mp199~200℃.

[0035] 1 HNMR (δ, 200MHz, DMSO-d6): 7.33(d, 1H, J9.9Hz), 6.17(d, 1H, J9.9Hz), 5.90(s, 1H), 5.5(s, 1H), 5.27(d ,1H,J AB 17.5Hz), 4.91 (d, 1H, J AB 17.5Hz), 4.8(s, 1H), 4.27(s, 1H), 3.22(s, 3H), 1.37(s, 3H), 0.79(s, 3H)

[0036] [Ref.Krajcsi, P.and Arányi, P...

Embodiment 3

[0038] Preparation of 11β,17α,21-trihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione-21-methanesulfonate

[0039] 11β, 17α, 21-trihydroxy-6α-methyl-pregna-1,4-diene-3,20-dione (methylprednisolone, 50g, 133.52mmol), with methanesulfonyl chloride (23.5ml, 303.62 mmol) was esterified to obtain 58.87 g of methanesulfonate, with a yield of 97.42%. Get 1g crude product, through flash column chromatography (CH 2 Cl 2 :CH 3 OH=10:0.2), yielding 0.9 g of analytical sample. Mp199~201℃.

[0040] 1 HNMR (δppm, DMSO-d6): 7.32 (d, 1H, J10.21Hz, C 1 -H), 6.17(d, 1H, J9.91Hz, C 2 -H), 5.81(s, 1H, C 4 -H), 5.48(s, 1H, C 11 -OH), 5.26(d, 1H, J17.8Hz, C 21 -H), 4.87(d, 1H, J17.6Hz, C 21 -H), 4.69(s, 1H, C 17 -OH), 4.27(s, 1H, C 11 -H), 3.23(s, 1H, SO 3 -CH 3 ), 1.37 (s, 3H, C 19 -CH 3 ), 1.04(d, 1H, J6.0Hz, C 6 -CH 3 ), 0.80(s, 1H, C 18 -CH 3 )

[0041] HRFAB (M+1): C 23 h 32 o 7 The theoretical value of S is 453.1941, and the measured value is 453.1949.

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Abstract

A glucocorticoid-type nitrogen-contained steroid compound, its preparing process, and its medical application for selectively suppressing the expression and activity of iNos and using its glucocorticoid medicine are disclosed.

Description

Technical field [0001] The invention relates to a nitrogen-containing steroid compound, and specifically provides a glucocorticoid nitrogen-containing steroid compound and a preparation method thereof. The nitrogen-containing steroid compound can selectively inhibit the expression and activity of iNOS when used as a medicine. The present invention also provides methods for preparing intermediates of these compounds. Background technique [0002] In the past ten years, people have made great progress in the research on the enzymology of NO production and the role of NO in physiology and pathology of many diseases. This makes people fully aware of the duality of NO, which is like a "double-edged sword" (Colasanti, M. and Suzuki, H. The dual personality of NO. TiPS. 2000, 21, 249-252), in addition to having In addition to one side, there is another side of pathological toxins. In view of the two sides of NO, pharmacists have developed two major classes of drugs, one can incre...

Claims

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Application Information

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IPC IPC(8): C07J5/00
Inventor 彭久合程津培朱兴族季新泉韩翀李秉桀
Owner NANKAI UNIV
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