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Prodrug of mycophenolic acid and production method of prodrug of mycophenolic acid

A liquid preparation and pharmacy technology, applied in the field of medicine, to achieve the effects of good water solubility and good permeability

Inactive Publication Date: 2019-12-03
SHANGHAI INNOFORTUNE BOITECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above factors prevent mycophenolate mofetil and mycofenac sodium from being directly made into liquid preparations (injections, oral solutions and eye drops, etc.)

Method used

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  • Prodrug of mycophenolic acid and production method of prodrug of mycophenolic acid
  • Prodrug of mycophenolic acid and production method of prodrug of mycophenolic acid
  • Prodrug of mycophenolic acid and production method of prodrug of mycophenolic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Embodiment 1, Preparation of (SZY1805-1H) compound

[0060] according to figure 1 The synthetic route diagram shown prepares the above compounds:

[0061] Add SZY-1805-2H (10.0g, 31.22mmol, 1.0eq, MW320.34) in 250ml round bottom flask, add 100mlDMF to dissolve, add imidazole (13.8g, 202.9mmol, 6.5eq, MW68.08) to dissolve, then TBSCl (18.82g, 124.87mmol, 4.0eq, MW150.7) was added in batches, and the reaction was stirred overnight at room temperature. TLC detects that the reaction is complete, and 150ml of EA and 200ml of water are added to the solution to form a layer. The aqueous phase was extracted three times with 50 ml EA, and the organic phases were combined. The organic phase was washed with 1% hydrochloric acid solution and 3-5 times with pure water (DMF was removed). The organic phase was dried with anhydrous sodium sulfate and rotary evaporated to obtain an oily substance. Add 50ml of THF, 50ml of water, and 50ml of acetic acid to the oil, stir at room te...

Embodiment 2

[0069] Embodiment 2, Preparation of (SZY1805-1a) compound

[0070] according to figure 2 The synthetic route diagram shown prepares the above compounds:

[0071] Add SZY-1805-2a (10.0g, 31.22mmol, 1.0eq, MW320.34) in 250ml round bottom flask, add 100mlDMF to dissolve, add imidazole (13.8g, 202.9mmol, 6.5eq, MW68.08) to dissolve, then TBSCl (18.82g, 124.87mmol, 4.0eq, MW150.7) was added in batches, and the reaction was stirred overnight at room temperature. TLC detects that the reaction is complete, and 150ml of EA and 200ml of water are added to the solution to form a layer. The aqueous phase was extracted three times with 50 ml EA, and the organic phases were combined. The organic phase was washed with 1% hydrochloric acid solution and 3-5 times with pure water (DMF was removed). The organic phase was dried with anhydrous sodium sulfate and rotary evaporated to obtain an oily substance. Add 50ml of THF, 50ml of water, and 50ml of acetic acid to the oil, stir at room t...

Embodiment 3

[0078] Embodiment 3, Preparation of (SZY1805-1f) compound

[0079] according to image 3 The synthetic route diagram shown prepares the above compounds:

[0080] Add SZY-1805-2f (10.0g, 31.22mmol, 1.0eq, MW320.34) in 250ml round bottom flask, add 100mlDMF to dissolve, add imidazole (13.8g, 202.9mmol, 6.5eq, MW68.08) to dissolve, then TBSCl (18.82g, 124.87mmol, 4.0eq, MW150.7) was added in batches, and the reaction was stirred overnight at room temperature. TLC detects that the reaction is complete, and 150ml of EA and 200ml of water are added to the solution to form a layer. The aqueous phase was extracted three times with 50 ml EA, and the organic phases were combined. The organic phase was washed with 1% hydrochloric acid solution and 3-5 times with pure water (DMF was removed). The organic phase was dried with anhydrous sodium sulfate and rotary evaporated to obtain an oily substance. Add 50ml of THF, 50ml of water, and 50ml of acetic acid to the oil, stir at room te...

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Abstract

The invention belongs to the field of medicines, and particularly relates to a prodrug of a mycophenolic acid and a production method of the prodrug of the mycophenolic acid. A structural general formula of the prodrug of the mycophenolic acid is as shown in a formula I as shown in the specification, wherein the compound as shown in the formula I has better aqueous humor permeability, aqueous solution stability and water solubility compared with the mycophenolic acid, and can be hydrolyzed into mycophenolate mofetil in aqueous humor, thus a drug concentration of the mycophenolic acid in the aqueous humor is significantly improved compared with that of mycophenolate sodium, and the drug concentration, which is observed in experiments, of the mycophenolic acid in the aqueous humor is two ormore times that of the mycophenolate sodium, so that the prodrug of the mycophenolic acid is more suitable for producing liquid preparations for eyes.

Description

technical field [0001] The invention belongs to the field of medicine, and in particular relates to a prodrug of mycophenolic acid and a preparation method thereof. Background technique [0002] Mycophenolate mofetil (Mycophenolate mofetil, MMF) is a potent, new type of immunosuppressive drug, which is the 2-morpholinyl ethyl esterification product of mycophenolic acid (mycophenolic acid, MPA). Inosine monophosphate dehydrogenase is an enzyme required for the synthesis of guanine nucleotides in lymphocytes and is therefore necessary for DNA synthesis and cell proliferation. MMF is a non-competitive, reversible inhibitor of this enzyme. The inhibitory effect of MPA on hypoxanthine monophosphate dehydrogenase can cause cells to stay in the G1 phase of the cell cycle. In T cells, MPA can inhibit the activity of cyclin-dependent kinase (CDK) and block the clearance of cDK inhibitor p27 (Kipl). In addition to its effect on lymphocyte proliferation, MMF can also inhibit the gly...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/88A61K31/343A61K9/08A61P37/06A61P29/00A61P27/02
CPCC07D307/88A61K9/08A61K9/0048A61P37/06A61P29/00A61P27/02
Inventor 刘国强刘伟
Owner SHANGHAI INNOFORTUNE BOITECH CO LTD
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