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Nitrate salt of anti-ulcer medicine

A technology of nitrates and drugs, used in the treatment and prevention of ulcer recurrence and most dyspepsia compositions, gastroprotective activity and anti-high gastric acid secretion active composition field, can solve the problem of unsatisfactory tolerance

Inactive Publication Date: 2006-04-05
NICOX SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these combinations are often unsatisfactory in terms of their tolerability

Method used

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  • Nitrate salt of anti-ulcer medicine
  • Nitrate salt of anti-ulcer medicine
  • Nitrate salt of anti-ulcer medicine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Preparation of cimetidine nitrate

[0051] 10 g of cimetidine was dissolved in 100 ml of acetonitrile / tetrahydrofuran / water 1:1:2 (volume ratio) mixture cooled at 4°C. A solution of 2.5 mL of 70% nitric acid in 10 mL of acetonitrile was gradually added. The solution was diluted with ether and the temperature was maintained at 4°C until the product started to precipitate. After several hours the precipitated solid was filtered off, washed with ether and dried. 12.1 g of cimetidine mononitrate were recovered, with a melting point of 158-159° C. (decomposition).

[0052] 1 H-NMR (D 2 O): 8,55 (1H, s), 3,83 (2H, s), 3,32 (2H, s), 2,77 (3H, s), 2,68 (2H, t), 2, 32(3H,s).

[0053] Elemental analysis:

[0054] Calculated value (%) C 38.09 H 5.43 N 31.09 S 10.17

[0055] Found value (%) C 37.99 H 5.41 N 31.16 S 10.25

Embodiment 2

[0057] Preparation of ranitidine nitrate

[0058] 5 g of ranitidine hydrochloride were dissolved in 140 ml of acetonitrile / methanol 6:1 mixture at 20°C. Add 4.2 grams of silver nitrate powder. The precipitated silver chloride is filtered off, washed with an acetonitrile / methanol 6:1 solution, the organic phases are combined, dried and worked up to give a dry residue. An amorphous solid corresponding to ranitidine mononitrate was thus obtained.

[0059] 1 H-NMR (D 2 O): 6,70(1H,d), 6,40(1H,d), 4,34(2H,s), 3,83(2H,s), 3,43(2H,t), 2, 93(2H, m), 2,87(9H, s).

[0060] Calculated value (%) C 41.37 H 6.14 N 18.56 S 8.50

[0061] Measured value (%) C 41.12 H 6.20 N 18.44 S 8.38

[0062] Pharmacological experiment

Embodiment 3

[0064] acute toxicity

[0065] In the form of a 2% w / v carboxymethylcellulose aqueous suspension, a group of 10 rats each weighing 20 g were orally administered a single dose of 100 mg / kg of the western medicine prepared in the preceding examples via intubation. Metidine and ranitidine nitrate.

[0066] These experimental animals were monitored for 14 days. No signs of toxicity were observed in any of the animals in this group.

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Abstract

Nitrate salt compositions with anti-ulcer medicines having formula(A)and(B) wherein the(A)class compounds: R=H, OCH3, OCHF2; R1=CH3, OCH3; R2=H, CH3; R3=CH3, CH2-CF3, (CH2)3-OCH3; wherein the(B)class compounds: R3, R4 equal to or different from each other, are respectively free valence hydrogen,-N=C(NH2)2, -CH2-N(CH3)2; Y=S, N-R6, CR7R8; X=O, S, N-R1; R2=H, CH3; n=0, 1; Z=N-CN, N-SO2NH2, CH-NO2 or formula(VIIA)R5=H, -NH-CH3, NH2; R6, R7, R8, R1, equal to or different from each other, are hydrogen, free valence. The invention also comprises the methods for the preparation of above salts.

Description

technical field [0001] The present invention relates to compositions for the treatment and prevention of ulcer recurrences and most dyspepsias. In particular, the present invention relates to compositions having improved gastroprotective activity as well as activity inhibiting hyperacid secretion. Background technique [0002] Products known in the art and commercially available for the treatment of ulcers are compounds with anti-acid secretion (acid secretion inhibitors). See eg "New Guide to Medicine & Drugs" Brit. Medical Assoc. Editor, 1997, pp. 108-109. Known products with higher therapeutic activity show high antacid activity and are used in acute and long-term (6 months or more) treatment. A drawback of these products is their poor, if any, gastroprotective activity. From a practical point of view, this means that the gastroprotection is suboptimal and especially inconvenient for long-term treatment. In this case, frequent dyspepsia due to a weakened gastric mucos...

Claims

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Application Information

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IPC IPC(8): C07D401/12C07D233/61C07D307/52C07D277/28C07D277/48A61K31/44A61K31/415A61K31/34A61K31/425C07D233/64A61K31/341A61K31/4164A61K31/426A61K31/4427A61K31/4439A61P1/04C07D213/00C07D233/00C07D233/54C07D277/20C07D277/30C07D277/42C07D307/54
CPCC07D277/48C07D277/28C07D307/52C07D233/64A61K31/44C07D401/12A61K31/425A61K31/415A61P1/04A61K31/34A61K2300/00
Inventor P·德尔索达托
Owner NICOX SA