Chemically modified small molecules
First Claim
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1. A compound selected from the group consisting of:
- 6-CH3-(OCH2CH2)5-O-naloxol;
6-CH3-(OCH2CH2)6-O-naloxol;
6-CH3-(OCH2CH2)8-O-naloxol; and
6-CH3-(OCH2CH2)9-O-naloxol;
or a pharmaceutically acceptable salt thereof, wherein the compound is an α
-6 isomer, a β
-6 isomer or a mixture of α
-6 and β
-6 isomers.
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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.
84 Citations
17 Claims
-
1. A compound selected from the group consisting of:
-
6-CH3-(OCH2CH2)5-O-naloxol; 6-CH3-(OCH2CH2)6-O-naloxol; 6-CH3-(OCH2CH2)8-O-naloxol; and 6-CH3-(OCH2CH2)9-O-naloxol; or a pharmaceutically acceptable salt thereof, wherein the compound is an α
-6 isomer, a β
-6 isomer or a mixture of α
-6 and β
-6 isomers.- View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17)
α
,β
-6-CH3-(OCH2CH2)6-O-naloxol;α
,β
-6-CH3-(OCH2CH2)8-O-naloxol; andα
,β
-6-CH3-(OCH2CH2)9-O-naloxol;or a pharmaceutically acceptable salt thereof.
-
-
3. The compound of claim 2, wherein the compound is α
- ,β
-6-CH3-(OCH2CH2)5-O-naloxol or a pharmaceutically acceptable salt thereof.
- ,β
-
4. The compound of claim 2, wherein the compound is α
- ,β
-6-CH3-(OCH2CH2)6-O-naloxol or a pharmaceutically acceptable salt thereof.
- ,β
-
5. The compound of claim 2, wherein the compound is α
- ,β
-6-CH3-(OCH2CH2)8-O-naloxol or a pharmaceutically acceptable salt thereof.
- ,β
-
6. The compound of claim 2, wherein the compound is α
- ,β
-6-CH3-(OCH2CH2)9-O-naloxol or a pharmaceutically acceptable salt thereof.
- ,β
-
7. The compound of claim 1, wherein the compound is selected from the group consisting of
α - -6-CH3-(OCH2CH2)5-O-naloxol;
α
-6-CH3-(OCH2CH2)6-O-naloxol;α
-6-CH3-(OCH2CH2)8-O-naloxol; andα
-6-CH3-(OCH2CH2)9-O-naloxol;or a pharmaceutically acceptable salt thereof.
- -6-CH3-(OCH2CH2)5-O-naloxol;
-
8. The compound of claim 7, wherein the compound is α
- -6-CH3-(OCH2CH2)5-O-naloxol or a pharmaceutically acceptable salt thereof.
-
9. The compound of claim 7, wherein the compound is α
- -6-CH3-(OCH2CH2)6-O-naloxol or a pharmaceutically acceptable salt thereof.
-
10. The compound of claim 7, wherein the compound is α
- -6-CH3-(OCH2CH2)8-O-naloxol or a pharmaceutically acceptable salt thereof.
-
11. The compound of claim 7, wherein the compound is α
- -6-CH3-(OCH2CH2)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
β - -6-CH3-(OCH2CH2)5-O-naloxol;
β
-6-CH3-(OCH2CH2)6-O-naloxol;β
-6-CH3-(OCH2CH2)8-O-naloxol; andβ
-6-CH3-(OCH2CH2)9-O-naloxol;or a pharmaceutically acceptable salt thereof.
- -6-CH3-(OCH2CH2)5-O-naloxol;
-
13. The compound of claim 12, wherein the compound is β
- -6-CH3-(OCH2CH2)5-O-naloxol or a pharmaceutically acceptable salt thereof.
-
14. The compound of claim 12, wherein the compound is β
- -6-CH3-(OCH2CH2)6-O-naloxol or a pharmaceutically acceptable salt thereof.
-
15. The compound of claim 12, wherein the compound is β
- -6-CH3-(OCH2CH2)8-O-naloxol or a pharmaceutically acceptable salt thereof.
-
16. The compound of claim 12, wherein the compound is β
- -6-CH3-(OCH2CH2)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.
Specification