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Claims for Patent: 5,866,591

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Claims for Patent: 5,866,591

Title: Stable formulations of remifentanil
Abstract:Stable formulations of 3-[4-methoxycarbonyl-4-[(1 -oxopropyl)phenylamino]-1-piperidine]propanoic acid, methyl ester, generally referred to as remifentanil, are disclosed. In particular, stabilized lyophilized solid composition are disclosed comprising certain acids, most preferably comprising glycine.
Inventor(s): Gatlin; Larry Alan (Chapel Hill, NC), Heiman; Shirley Ann (Cary, NC), Lewis; Janet Sue (Cary, NC)
Assignee: Glaxo Wellcome Inc. (Research Triangle Park, NC)
Application Number:08/926,930
Patent Claims: 1. A solid composition comprising remifentanil and glycine, wherein said composition maintains a room temperature shelf life stability of at least two years.

2. The composition of claim 1 wherein said composition is a lyophilized solid composition.

3. A solid composition comprising remifentanil and at least one agent selected from the group consisting of ascorbic acid, citric acid, maleic acid, phosphoric acid, glycine, succinic acid, or tartaric acid.

4. The composition of claim 3 wherein said composition comprises less than 3% by weight water.

5. The composition of claim 3 wherein said agent is glycine.

6. The composition of claim 5 further comprising sodium chloride, polyvinylpyrolidone, or mannitol.

7. The composition of claim 5 wherein remifentanil and glycine comprise at least 20% by weight of the composition.

8. The composition of claim 5 wherein remifentanil and glycine comprise at least 50% by weight of the composition.

9. The composition of claim 5 wherein said composition gives an aqueous solution having a pH of from pH 1.5 to pH 5, when dissolved in an amount of aqueous liquid to give a composition suitable for intravenous administration to a patient.

10. The composition of claim 5 wherein said composition gives an aqueous solution having a pH of from pH 2.5 to pH 3.5, when dissolved in an amount of aqueous liquid to give a composition suitable for intravenous administration to a patient.

11. The composition of claim 5 wherein said composition gives an aqueous solution having a pH of from pH 2.8 to pH 3.2, when dissolved in an amount of aqueous liquid to give a composition suitable for intravenous administration to a patient.

12. The composition of claim 5 wherein said composition is lyophilized.

13. The composition of claim 12 wherein said composition is sterilized.

14. The composition of claim 5 wherein the ratio by weight of other components to remifentanil is less than or equal to 75 to 1.

15. The composition of claim 5 wherein the ratio by weight of other components to remifentanil is less than or equal to 40 to 1.

16. The composition of claim 5 wherein the ratio by weight of other components to remifentanil is less than or equal to 15 to 1.

17. The composition of claim 5 wherein glycine comprises at least 50% by weight of the composition.

18. The composition of claim 5 wherein said composition comprises, for each part by weight of remifentanil free base or hydrochloride salt, from 2 to 20 parts by weight of glycine, and from 0 to 50 parts by weight of other ingredients.

19. A complex of remifentanil hydrochloride, glycine, and water.

20. Remifentanil glycinate.
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