Salt compound formed by aceclofenac and organic base as well as composition and uses thereof

A salt compound, aceclofenac technology, applied in the direction of organic chemistry, drug combination, non-central analgesics, etc., can solve problems such as destruction, inability to take effect quickly, and pain relief for patients

Inactive Publication Date: 2008-06-25
王文菊
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because aceclofenac contains an ester bond, it is easily hydrolyzed under acidic and alkaline conditions, and the solution of the oral preparation is easily destroyed by acidic gastric juice, and for pa...

Method used

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  • Salt compound formed by aceclofenac and organic base as well as composition and uses thereof
  • Salt compound formed by aceclofenac and organic base as well as composition and uses thereof
  • Salt compound formed by aceclofenac and organic base as well as composition and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0022] Example 1 Aceclofenac arginine (1:1, AR)

[0023] Dissolve 35.4 g (0.1 mol) of aceclofenac in 300 mL of ethanol (95%), heat and stir, slowly add 17.4 g (0.1 mol) of arginine in portions, heat to reflux for 30 min after the reaction solution is clear, cool and crystallize , precipitated solid, filtered, washed the filter cake with cold ethanol, and dried in an oven at 60°C to obtain 48.4g of the product.

[0024]

[0025] 1HNMR (DMSO 12 ): 1.56(2H, m, 3#), 1.68(2H, q, 2#), 3.03(2H, t, 4#), 3.29(1H, t, 1#), 3.82(2H, s, 6# ), 4.26(2H, s, 5#), 6.25(1H, d, 10#), 6.85(1H, t, 8#), 7.06(1H, d, 7#), 7.18(1H, t, 12# ), 7.22(1H, t, 9#), 7.29(1H, s, 6'), 7.51(2H, d, 11#, 13#), 8.0(5H, overlapping, 2'(2), 3', 4', 5' (1)).

example 2

[0026] Example 2 Aceclofenac arginine (2:1, A 2 R)

[0027] Dissolve 35.4g (0.1mol) of aceclofenac in 150mL of ethanol (95%), heat and stir, slowly add 8.7g (0.05mol) of arginine in portions, heat to reflux for 30min after the reaction solution is clear, add isopropyl 350ml of alcohol was cooled and crystallized, and a solid was precipitated, filtered, the filter cake was washed with cold ethanol, and dried in an oven at 60°C to obtain 39.3g of the product.

[0028]

[0029] 1HNMR (DMSO+D 2 O): 1.54(2H, m, 3#), 1.68(2H, q, 2#), 3.06(2H, t, 4#), 3.36(1H, t, 1#), 3.83(4H, s, 6 #), 4.43(4H, s, 5#), 6.23(2H, d, 10#), 6.86(2H, t, 8#), 7.06(2H, t, 7#), 7.17(2H, t, 12 #), 7.21 (2H, t, 9#), 7.48 (4H, d, 11#, 13#).

example 3

[0030] Example 3 Aceclofenac lysine

[0031] Dissolve 35.4g (0.1mol) of aceclofenac in a mixture of 200mL ethanol (95%) and 80ml water, heat and stir, slowly add 14.6g (0.1mol) of lysine in portions, and heat after the reaction solution becomes clear. Reflux for 30 minutes, cool and crystallize, precipitate solids, filter, wash the filter cake with cold ethanol, and dry in an oven at 60°C to obtain 46.3 g of the product.

[0032]

[0033] 1HNMR (D 2 O): 1.434(2H, m, 3#), 1.63(2H, m, 4#), 1.83(2H, q, 2#), 2.93(2H, t, 5#), 3.69(1H, t, 1 #), 3.79(2H, s, 7#), 4.38(2H, s, #6), 6.18(1H, d, 11#), 6.75(1H, t, 9#), 6.78(1H, d, 8 #), 6.82 (1H, t, 13#), 7.12 (1H, t, 10#), 7.10 (2H, d, 12#, 14#).

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PUM

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Abstract

The invention discloses a salt compound formed through the aceclofenac and the organic base and the assemblage and the use. The general formula of the salt compound is AxR mH2O; wherein, A is the aceclofenac (CAS RN: 89796-99-6) and x is 1, 2; R is nitrogen organic base and can be amine and basic amino acid. The amine is most suitable for being selected from the Meglumine and trometamol; the basic amino acid is most suitable for being selected from the Arginine, Lysine, Ornithine, Histidine and Citrulline. The spatial configurations of the amino acids include the DL type, D type, L type and optimized L type; m is 0, 1, 2, 3, 4, 5 and 6. The compound and the assemblage to which the invention relates can be applied to the diseases such as the inflammation and pain, sprain, pull, and other soft tissue injuries and fever, etc., caused by the rheumatoid arthritis, rheumatoid arthritis, osteoarthritis, spondylitis, etc. of the human beings or animals.

Description

technical field [0001] The present invention relates to a salt compound formed by aceclofenac and an organic base, a preparation method thereof, a pharmaceutical composition containing one or more of these compounds, and the application of the compound and the pharmaceutical composition. Background technique [0002] Aceclofenac is a phenylacetic acid non-steroidal anti-inflammatory analgesic drug, which is a derivative of diclofenac. The English name is Aceclofenac (CAS RN: 89796-99-6), the chemical name is 2-2,6-dichlorophenyl-amino-phenylacetoxyacetic acid, and the molecular formula is C 16 h 13 Cl 2 NO 4 , the molecular weight is 354.19. [0003] [0004] Structurally, aceclofenac is related to diclofenac, aclofenac, and fenclofenac. In clinical practice, the pharmacological effects of aceclofenac are compared with other non-steroidal drugs (NSAIDs), in acute and chronic inflammation experimental models, aceclofenac shows a significant range of anti-inflammatory ...

Claims

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Application Information

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IPC IPC(8): C07C229/42A61K31/222A61P29/00C07C279/14C07C229/26C07C215/10
Inventor 王文菊
Owner 王文菊
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