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Details for Patent: 8,034,825

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Details for Patent: 8,034,825

Title:Chemically modified small molecules
Abstract: The invention provides small molecule drugs that are chemically modified by covalent attachment of a water-soluble oligomer obtained from a monodisperse or bimodal water-soluble oligomer composition. A conjugate of the invention, when administered by any of a number of administration routes, exhibits a reduced biological membrane crossing rate as compared to the biological membrane crossing rate of the small molecule drug not attached to the water-soluble oligomer.
Inventor(s): Bentley; Michael D. (Huntsville, AL), Viegas; Tacey X. (Madison, AL), Goodin; Richard R. (Fayerville, TN), Cheng; Lin (Huntsville, AL), Zhao; Xuan (Huntsville, AL)
Assignee: Nektar Therapeutics (San Francisco, CA)
Filing Date:Jun 24, 2010
Application Number:12/822,935
Claims:1. A compound selected from the group consisting of: 6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.5-O-naloxol; 6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.6-O-naloxol; 6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.8-O-naloxol; and 6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.9-O-naloxol; or a pharmaceutically acceptable salt thereof, wherein the compound is an .alpha.-6 isomer, a .beta.-6 isomer or a mixture of .alpha.-6 and .beta.-6 isomers.

2. The compound of claim 1, wherein the compound is selected from the group consisting of .alpha.,.beta.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.5-O-naloxol; .alpha.,.beta.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.6-O-naloxol; .alpha.,.beta.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.8-O-naloxol; and .alpha.,.beta.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.9-O-naloxol; or a pharmaceutically acceptable salt thereof.

3. The compound of claim 2, wherein the compound is .alpha.,.beta.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.5-O-naloxol or a pharmaceutically acceptable salt thereof.

4. The compound of claim 2, wherein the compound is .alpha.,.beta.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.6-O-naloxol or a pharmaceutically acceptable salt thereof.

5. The compound of claim 2, wherein the compound is .alpha.,.beta.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.8-O-naloxol or a pharmaceutically acceptable salt thereof.

6. The compound of claim 2, wherein the compound is .alpha.,.beta.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.9-O-naloxol or a pharmaceutically acceptable salt thereof.

7. The compound of claim 1, wherein the compound is selected from the group consisting of .alpha.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.5-O-naloxol; .alpha.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.6-O-naloxol; .alpha.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.8-O-naloxol; and .alpha.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.9-O-naloxol; or a pharmaceutically acceptable salt thereof.

8. The compound of claim 7, wherein the compound is .alpha.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.5-O-naloxol or a pharmaceutically acceptable salt thereof.

9. The compound of claim 7, wherein the compound is .alpha.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.6-O-naloxol or a pharmaceutically acceptable salt thereof.

10. The compound of claim 7, wherein the compound is .alpha.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.8-O-naloxol or a pharmaceutically acceptable salt thereof.

11. The compound of claim 7, wherein the compound is .alpha.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.9-O-naloxol or a pharmaceutically acceptable salt thereof.

12. The compound of claim 1, wherein the compound is selected from the group consisting of .beta.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.5-O-naloxol; .beta.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.6-O-naloxol; .beta.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.8-O-naloxol; and .beta.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.9-O-naloxol; or a pharmaceutically acceptable salt thereof.

13. The compound of claim 12, wherein the compound is .beta.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.5-O-naloxol or a pharmaceutically acceptable salt thereof.

14. The compound of claim 12, wherein the compound is .beta.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.6-O-naloxol or a pharmaceutically acceptable salt thereof.

15. The compound of claim 12, wherein the compound is .beta.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.8-O-naloxol or a pharmaceutically acceptable salt thereof.

16. The compound of claim 12, wherein the compound is .beta.-6-CH.sub.3-(OCH.sub.2CH.sub.2).sub.9-O-naloxol or a pharmaceutically acceptable salt thereof.

17. A pharmaceutical composition comprising a compound of any one of claims 1-16 or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.
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