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Novel steroid compound and uses thereof

A compound and reaction technology, applied in the field of [17α, can solve the problems of easy explosion, high risk, low yield, etc., and achieve the effect of high safety performance and operability, excellent yield and cost, and simple circuit

Inactive Publication Date: 2008-05-14
TIANJIN PHARMA GROUP CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Aiming at the historical problems of [17α, 16α-d] oxazoline steroids and their preparation methods, we have designed a new process route for the synthesis of oxazoline steroids by taking advantage of our company’s technical advantages, and selected the appropriate 16, 17-epoxypregnane as the starting material, after 16,17-epoxy ring-opening, and then cyclization into 16,17-oxazole compound, successfully solved the azide method, which is easy to explode, high risk, complicated products, and high yield Low; and the cost of platinum oxide catalyst is expensive and other key issues

Method used

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  • Novel steroid compound and uses thereof
  • Novel steroid compound and uses thereof
  • Novel steroid compound and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Condensation, ring opening reaction

[0048] Add 32.4g of 1,4,9-triene-16,17-epoxy-3,20-diketone pregna (ZL200210014479.5) and 205ml of tetrahydrofuran into the reaction flask. After replacing the air with nitrogen, add Semicarbazide 20.8gH 2 NNH CONH 2 , 0.205g p-toluenesulfonic acid, temperature control 20-25℃, react for 2 hours, take samples for TLC analysis until there is no raw material, change to ammonia gas, the temperature is 20-25℃, stop the gas conduction after 3 hours, and then react for 1 hour , thin-layer analysis to no raw materials, exhaust the ammonia with atmospheric nitrogen, dilute the reaction solution in 1200ml of saturated sodium chloride water, stir for 1 hour, let stand for 1 hour, filter, and dry to obtain 34g of compound 16α-hydroxyl- 17α-Amino-1,4,9-trienpregna-3-one-20-semicarbazone.

[0049] Cyclization reaction

[0050] Add 30g of 16α-hydroxy-17α-amino-1,4,9-triene-pregn-3-one-20-semicarbazone, 150ml of acetic anhydride, 150ml of acetic...

Embodiment 2

[0056] Condensation, ring opening reaction

[0057] Add 30g of 16,17-epoxy-11-hydroxyl-1,4-dienepregna-3,20-dione (ZL200210014479.5), 180ml of dimethylformamide into the reaction flask, and feed nitrogen After replacing the air, add semicarbazide 18gH 2 NNH CONH 2 , 0.18g p-toluenesulfonic acid, react at a temperature of 25-30°C for 2 hours, take a sample for thin-layer analysis until there is no raw material, change to ammonia gas, the temperature is 10-15°C, stop the gas conduction after 5 hours, and then react for 1.5 hour, thin-layer analysis to no raw materials, exhaust the ammonia with atmospheric nitrogen, dilute the reaction solution in 800ml of saturated sodium chloride water, extract three times with 150ml of chloroform, combine the organic phases, wash with water until neutral, concentrate under reduced pressure, Replace with ethyl ester 2 to 3 times when the volume reaches a small size, and the precipitated material is cooled at 0 to 5°C for 1 hour, filtered and ...

Embodiment 3

[0065] Synthetic Deflazacort:

[0066] The 2′-methyl-5′βH-pregna-1,4,9-triene-[17α,16α-d]-oxazole-3,20-dione obtained in Example 1 was used as the raw material.

[0067] 1) Ethylene bond addition reaction:

[0068] Add 18.3g of 2′-methyl-5′βH-pregna-1,4,9-triene-[17α,16α-d]-oxazole-3,20-dione and 183ml of tetrahydrofuran into the reaction flask, After dissolving, cool down to 0±5°C, quickly add 110ml of 4.8% perchloric acid aqueous solution dropwise, then add 22g of N-bromosuccinimide, react for 30 minutes, take samples for lamellar analysis to determine the end point, add 30ml of saturated sodium sulfite The aqueous solution is discolored by reaction. After stirring for 30 minutes at 10±2°C, pour the reaction solution into 1200ml of saturated sodium chloride ice water for dilution, stir for 1 hour, let stand for 1 hour, filter, wash with water until neutral, and dry to obtain 22g of the compound 11-Hydroxy-9-bromo-2'-methyl-5'βH-pregna-1,4,9-triene-[17α,16α-d]-oxazole-3,20-...

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Abstract

The invention relates to new steroid compounds and the application, in particular to [17 Alpha, 16 Alpha -d] oxazoline steroid compounds and the preparation method. The new compound (II) and compound (III) from the invention protected by ketol 20, are the important intermediates in synthesizing [17 Alpha, 16 Alpha -d] oxazoline steroid compounds. The invention also provides the application of compound (I), compound (II) and compound (III) in preparing compound (V). The invention has the advantages of high feasibility and strong operability of the process, ability to obtain intermediates through general chemical purification without high risk operation and expensive reagents, and high industrialization factor.

Description

technical field [0001] The present invention relates to new steroidal compounds and applications thereof, in particular to [17α, 16α-d] oxazoline steroidal compounds and their preparation methods. Background technique [0002] [17α, 16α-d]oxazoline steroids are a very useful class of steroidal active compounds, and the representative drug is deflazacort. Deflazacort is a third-generation glucocorticoid steroidal anti-inflammatory drug, an oxazoline derivative of prednisolone, mainly used for rheumatoid arthritis, nephrotic syndrome, systemic lupus erythematosus, uvea Inflammation, sarcoidosis treatment and organ transplantation. The literature Drugs Res.30 (II), Nr, 9 (1980) mentioned that the anti-inflammatory activity of deflazacort was significantly stronger than that of prednisolone, and the literature Drugs50 (2): 317-313, 1995 mentioned that in rheumatic joints Deflazacort is as effective as prednisone or hexamethylprednisolone in the treatment of arthritis and is co...

Claims

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Application Information

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IPC IPC(8): C07J7/00C07J71/00
CPCY02P20/55
Inventor 李媛卢彦昌李金禄孙朝晖
Owner TIANJIN PHARMA GROUP CORP
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