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Preparation methods of S-(+)-ibuprofen tromethamine salt and oral solution thereof

A technology for dexibuprofen and oral solution, which is applied in the preparation of carboxylate salts, organic compounds, amino hydroxyl compounds, etc., can solve the problems of low water solubility of dexibuprofen, and achieve accurate dosage and good taste Improvement, water-solubility enhancement effect

Inactive Publication Date: 2012-03-21
NANJING TEFENG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The water solubility of the drug compound has been effectively improved, and its onset is faster than that of Dexibuprofen. After being made into an oral solution, its mouthfeel is obviously better than that of Dexibuprofen, and it is more suitable for children and patients with dysphagia. Gastrointestinal side effects such as gastrointestinal ulcers and bleeding caused by ibuprofen have greatly improved the shortcomings of low water solubility and spicy taste of ibuprofen, and are suitable for clinical antipyretic, analgesic and anti-inflammatory applications

Method used

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  • Preparation methods of S-(+)-ibuprofen tromethamine salt and oral solution thereof
  • Preparation methods of S-(+)-ibuprofen tromethamine salt and oral solution thereof
  • Preparation methods of S-(+)-ibuprofen tromethamine salt and oral solution thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: Preparation of dextroibuprofen tromethamine salt

[0045] Accurately weigh 2.422g of tromethamine and dissolve it in 25mL of distilled water, heat to 50℃ to dissolve, and accurately weigh 4.130g of dextro-ibuprofen (the molar ratio of tromethamine is 1:1) in a mill Add 17 mL of 95% ethanol to a round-bottomed bottle. After stirring to dissolve, slowly add the above tromethamine aqueous solution, stirring at room temperature until white precipitation appears, and the solvent is evaporated to obtain the crude product. Recrystallized with 95% ethanol, the yield is 94.6 %. The measured melting point is 158~162℃, and the water solubility is 5.0~6.0mg / mL.

[0046] 1 HNMR (ppm): 0.876 (d, H a ), 1.296(s, H b ), 1.798(m, H c ), 3.390(s, H d ), 5.816(m, H e ), 7.101(q, H e ), 2.428(t, H f )

[0047] IR(kBr)(cm -1 ): 1183.77cm -1 It is the stretching vibration of dextroibuprofen carboxyl group, 1403.29cm -1 And 1,631.73cm -1 It is the characteristic band of carboxyl ion ban...

Embodiment 2

[0048] Example 2: Preparation of dextroibuprofen tromethamine salt

[0049] Accurately weigh 2.450g of tromethamine and dissolve it in 50mL of distilled water, heat to 40℃ to dissolve, and accurately weigh 8.315g of dextro-ibuprofen (the molar ratio of tromethamine is 2:1) in a mill Add 30 mL of 95% ethanol to a round-bottomed flask. After stirring to dissolve, the tromethamine aqueous solution is slowly added dropwise and stirred at room temperature until white precipitation appears. The solvent is evaporated to obtain the crude product, which is recrystallized with acetone. The yield is 61.73%. The measured melting point is 158~162℃, and the water solubility is 5.0~6.0mg / mL.

[0050] 1 HNMR (ppm): 0.876 (d, H a ), 1.296(s, H b ), 1.798(m, H c ), 3.390(s, H d ), 5.816(m, H e ), 7.101(q, H e ), 2.428(t, H f )

[0051] IR(kBr)(cm -1 ): 1183.77cm -1 It is the stretching vibration of dextroibuprofen carboxyl group, 1403.29cm -1 And 1,631.73cm -1 It is the characteristic band of carboxy...

Embodiment 3

[0052] Example 3: Preparation of dextroibuprofen tromethamine salt

[0053] Accurately weigh 2.320g of tromethamine and dissolve in 50mL of distilled water, heat to 60℃ to dissolve, and accurately weigh 2.006g of dextro-ibuprofen (molar ratio of tromethamine is 1:2) in a mill Add 30 mL of 95% ethanol to a round-bottomed flask. After stirring to dissolve, slowly add dropwise the above tromethamine aqueous solution, stir at room temperature until white precipitation appears, distill off the solvent to obtain a crude product, and recrystallize with methanol. The yield is 70.65%. The measured melting point is 158~162℃, and the water solubility is 5.0~6.0mg / mL.

[0054] 1 HNMR (ppm): 0.876 (d, H a ), 1.296(s, H b ), 1.798(m, H c ), 3.390(s, H d ), 5.816(m, H e ), 7.101(q, H e ), 2.428(t, H f )

[0055] IR(kBr)(cm -1 ): 1183.77cm -1 It is the stretching vibration of dextroibuprofen carboxyl group, 1403.29cm -1 And 1,631.73cm -1 It is the characteristic band of carboxyl ion band, 714.69cm ...

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Abstract

The invention discloses preparation methods of S-(+)-ibuprofen tromethamine salt and an oral solution thereof. The preparation method of the S-(+)-ibuprofen tromethamine salt comprises the following steps: based as S-(+)-ibuprofen and tromethamine as starting raw materials, slowly dropping the aqueous solution of tromethamine in an organic solvent solution containing 50%-99% of S-(+)-ibuprofen at room temperature under stirring until precipitate emerges, then vaporizing to remove the solvent and crystallizing to obtain the S-(+)-ibuprofen tromethamine salt with higher water solubility. The invention also discloses a formula and a preparation method of the oral solution preparation of the S-(+)-ibuprofen tromethamine salt.

Description

Technical field [0001] The invention relates to a dextroibuprofen tromethamine salt and a preparation method of its oral solution, belonging to the technical field of drug synthesis and pharmaceutical preparations, and more specifically to a dextroibuprofen tromethamine salt The synthesis and preparation method of the salt oral solution. Background technique [0002] The oral solution of dextroibuprofen tromethamine salt contains the active ingredient dextroibuprofen tromethamine salt. Dexibuprofen tromethamine salt is (S)-2-(4-isobutylphenyl)propionic acid 2-amino-2-hydroxymethyl-1,3-propanediol salt (dexibuprofentromethamine salt). Dextro-ibuprofen is the right-handed enantiomer of ibuprofen. Ibuprofen consists of the same proportions of L-ibuprofen and Dex-ibuprofen. The pharmacological activity of ibuprofen is mainly produced by Dex-ibuprofen. The side effect of dextro-ibuprofen is only 1 / 3 of that of lev-ibuprofen, and its elimination from the body is more complete. After...

Claims

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Application Information

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IPC IPC(8): C07C215/10C07C213/08C07C57/30C07C51/41A61K31/205A61K9/08A61P29/00
Inventor 陶亮何秀丽温天文李述彬朱怀柏夏秋月孙柏旺
Owner NANJING TEFENG PHARMA
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