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Details for Patent: 6,569,889

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Details for Patent: 6,569,889

Title: Amino ceramide-like compounds and therapeutic methods of use
Abstract:Novel amino ceramide-like compounds are provided which inhibit glucosyl ceramide (GlcCer) formation by inhibiting the enzyme GlcCer synthase, thereby lowering the level of glycosphingolipids. The compounds of the present invention have improved GlcCer synthase inhibition activity and are therefore highly useful in therapeutic methods for treating various conditions and diseases associated with altered glycosphingolipid levels.
Inventor(s): Shayman; James A. (Ann Arbor, MI), Radin; Norman S. (Menlo Park, CA)
Assignee: The Regents of the University of Michigan (Ann Arbor, MI)
Filing Date:May 31, 2001
Application Number:09/870,870
Claims:1. A compound selected from the group consisting of the formula ##STR5##

where R.sub.1 is 4-hydroxyphenyl or 3,4-ethylendioxy phenyl; R.sub.2 is an aliphatic chain having 10 to 18 carbons; and R.sub.3 is pyrrolidino.

2. The compound of claim 1, wherein R.sup.1 is 4-hydroxyphenyl.

3. The compound of claim 1, wherein R.sup.1 is 3,4-ethylenedioxy phenyl.

4. The compound of claim 1, wherein R.sup.2 is C.sub.15 H.sub.31.

5. The compound of claim 1, wherein the compound is 4'-hydroxy-1-phenyl-2-palmitoylamino-3-pyrrolidino-1-propanol or pharmaceutically acceptable salts thereof.

6. The compound of claim 1, wherein the compound is 3',4'-ethylenedioxy-1-phenyl-2-palmitoylamino-3-pyrrolidino-1-propanol or pharmaceutically acceptable salts thereof.

7. A method of inhibiting growth of cancer cells in a mammal, comprising the step of administering to the mammal a therapeutically effective amount of a composition comprising the compound of claim 1, wherein said cancer cells are sensitive to said compound.

8. The method of claim 7, wherein the growth of the cancer cells is inhibited by increasing ceramide levels in the cancer cells to a toxic level.

9. A method for inhibiting the growth of cancer cells in a mammal, comprising the step of administering to the mammal a therapeutically effective amount of a composition comprising a compound selected from the group consisting of D-t-3',4'-ethylenedioxy-1-phenyl-2-palmitoylamino-3-pyrrolidino-1-propanol D-t-4-hydroxy-1-phenyl-2-palmitoylamino-3-pyrrolidino-1-propanol, pharmaceutically acceptable salts, and mixtures thereof, wherein said cancer cells are sensitive to said compound composition.

10. The method of claim 9, wherein the compound is D-t-3',4'-ethylenedioxy-1-phenyl-2-palmitoylamino-3-pyrrolidino-1-propanol or pharmaceutically acceptable salts thereof.

11. The method of claim 9, wherein the compound is D-t-4'-hydroxy-1-phenyl-2-palmitoylamino-3-pyrrolidino-1-propanol or pharmaceutically acceptable salts thereof.

12. A method of treating a patient having a drug resistant tumor, comprising the step of administering to the patient a therapeutically effective amount of a composition comprising the compound of claim 1, wherein the tumor is sensitive to said compound.

13. A method of treating a patient having a drug resistant tumor, comprising the step of administering to the patient a therapeutically effective amount of a composition comprising a compound selected from the group consisting of D-t-3',4'-ethylenedioxy-1-phenyl-2-palmitoylamino-3-pyrrolidino-1-propanol , D-t-4-hydroxy-1-phenyl-2-palmitoylamino-3-pyrrolidino-1-propanol, pharmaceutically acceptable salts, and mixtures thereof, wherein the tumor is sensitive to said compound.

14. The method of claim 13, wherein the compound is D-t-3',4'-ethylenedioxy-1-phenyl-2-palmitoylamino-3-pyrrolidino-1-propanol or pharmaceutically acceptable salts thereof.

15. The method of claim 13, wherein the compound is D-t-4'-hydroxy-1-phenyl-2-palmitoylamino-3-pyrrolidino-1-propanol or pharmaceutically acceptable salts thereof.

16. A method of reducing tumor angiogenesis in a patient, comprising the step of administering to the patient a therapeutically effective amount of a composition comprising the compound of claim 1, wherein said angiogenesis is sensitive to said compound.

17. A method of reducing tumor angiogenesis in a patient, comprising the step of administering to the patient a therapeutically effective amount of a composition comprising a compound selected from the group consisting of D-t-3',4'-ethylenedioxy-1-phenyl-2-palmitoylamino-3-pyrrolidino-1-propanol , D-t-4-hydroxy-1-phenyl-2-palmitoylamino-3-pyrrolidino-1-propanol, pharmaceutically acceptable salts, and mixtures thereof, wherein said angiogenesis is sensitive to said compound.

18. The method of claim 17, wherein the compound is D-t 3',4'-ethylenedioxy-1-phenyl-2-palmitoylamino-3-pyrrolidino-1-propanol or pharmaceutically acceptable salts thereof.

19. The method of claim 17, wherein the compound is D-t-4'-hydroxy-1-phenyl-2-palmitoylamino-3-pyrrolidino-1-propanol or pharmaceutically acceptable salts thereof.
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