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Details for Patent: 7,850,008

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Details for Patent: 7,850,008

Title:Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy
Abstract: The present invention relates to compounds being esters of 5-aminolevulinic acids or pharmaceutically acceptable salts thereof, including compounds of formula (I) R22N--CH2COCH2-CH2CO--OR1 (wherein R1 may represent alkyl optionally substituted by hydroxy, alkoxy, acyloxy, alkoxycarbonyloxy, amino, aryl, oxo or fluoro groups and optionally interrupted by oxygen, nitrogen, sulphur or phosphorus atoms; and R2 represents a hydrogen atom or a group R1, and both R2 groups may be the identical or different), and their use in diagnosis and photochemotherapy of disorders or abnormalities of external or internal surfaces of the body, and products and kits for performing the invention.
Inventor(s): Gierskcky; Karl E. (Hosle, NO), Moan; Johan (Oslo, NO), Peng; Qian (Oslo, NO), Steen; Harald (Oslo, NO), Warloe; Trond (Oslo, NO), Bjorseth; Alf (Oslo, NO)
Assignee: Photocure ASA (Oslo, NO)
Filing Date:May 07, 2009
Application Number:12/437,444
Claims:1. A method for the diagnosis of disorders or abnormalities of an internal surface of the body, comprising: (i) administering to the sites of investigation or affected surfaces a composition comprising a compound of formula (I) R.sup.2.sub.2N--CH.sub.2COCH.sub.2--CH.sub.2CO--OR.sup.1 (I) wherein, R.sup.1 is alkyl; and each R.sup.2 is independently hydrogen or alkyl; wherein each alkyl of R.sup.1 and R.sup.2 is optionally substituted by hydroxy, alkoxy, acyloxy, alkoxycarbonyloxy, amino, aryl, oxo or fluoro groups and is optionally interrupted by oxygen atoms; or a pharmaceutically acceptable salt thereof; and (ii) exposing said sites or surfaces to light, wherein the internal surface of the body is the lining of the intestine.

2. The method of claim 1, wherein the composition is in the form of a tablet or capsule suitable for oral administration.

3. The method of claim 1, wherein the composition is in the form of a solution suitable for oral or rectal administration.

4. The method of claim 3, wherein the composition further comprises an aqueous carrier.

5. The method of claim 1, claim 2, claim 3, or claim 4, wherein, in the compound of formula (I), R.sup.1 represents an unsubstituted alkyl group and each R.sup.2 is hydrogen.

6. The method of claim 5, wherein the compound of formula (I) is ALA-methyl ester, ALA-ethyl ester, ALA-propyl ester, or ALA-hexyl ester.

7. The method of claim 6, wherein the method is used to determine whether colorectal cancer may be present.

8. The method of claim 7, wherein the compound of formula (I) is ALA-hexyl ester.

9. The method of claim 8, wherein the compound in the composition is the hydrochloride salt of ALA-hexyl ester.

10. The method of claim 1, wherein the concentration of the compound in the composition is 10-50% (w/w).

11. The method of claim 10, wherein the concentration of the compound is 15-30% (w/w).

12. The method of claim 1, wherein a period of 0.5-48 hours is permitted to elapse between administering the composition and exposing the sites or surfaces to light.

13. The method of claim 12, wherein a period of 1 to 10 hours is permitted to elapse between administering the composition and exposing the sites or surfaces to light.

14. The method of claim 1, wherein the light has a wavelength of 350-640 nm.

15. A method for the diagnosis of disorders or abnormalities of an internal surface of the body, comprising: (i) administering to the sites of investigation or affected surfaces a composition comprising (a) a compound of formula (I) R.sup.2.sub.2N--CH.sub.2COCH.sub.2--CH.sub.2CO--OR.sup.1 (I) wherein, R.sup.1 is alkyl; and each R.sup.2 is independently hydrogen or alkyl; wherein each alkyl of R.sup.1 and R.sup.2 is optionally substituted by hydroxy, alkoxy, acyloxy, alkoxycarbonyloxy, amino, aryl, oxo or fluoro groups and is optionally interrupted by oxygen atoms; or a pharmaceutically acceptable salt thereof, and (b) one or more fatty substances; and (ii) exposing said sites or surfaces to light, wherein the internal surface of the body is the lining of the intestine.

16. The method of claim 15, wherein the composition is in the form of a tablet or capsule suitable for oral administration.

17. The method of claim 15, wherein the composition is in the form of a solution suitable for oral or rectal administration.

18. The method of claim 17, wherein the composition comprises an aqueous carrier.

19. The method of claim 15, claim 16, claim 17, or claim 18, wherein, in the compound of formula (I), R.sup.1 represents an unsubstituted alkyl group and each R.sup.2 is hydrogen.

20. The method of claim 19, wherein the compound of formula (I) is ALA-methyl ester, ALA-ethyl ester, ALA-propyl ester, or ALA-hexyl ester.

21. The method of claim 20, wherein the method is used to determine whether colorectal cancer may be present.

22. The method of claim 21, wherein the compound of formula (I) is ALA-hexyl ester.

23. The method of claim 22, wherein the compound in the composition is the hydrochloride salt of ALA-hexyl ester.

24. The method of claim 15, wherein the concentration of the compound in the composition is 10-50% (w/w).

25. The method of claim 24, wherein the concentration of the compound is 15-30% (w/w).

26. The method of claim 15, wherein a period of 0.5-48 hours is permitted to elapse between administering the composition and exposing the sites or surfaces to light.

27. The method of claim 26, wherein a period of 1 to 10 hours is permitted to elapse between administering the composition and exposing the sites or surfaces to light.

28. The method of claim 15, wherein the light has a wavelength of 350-640 nm.

29. A pharmaceutical composition comprising (a) a compound of formula (I) R.sup.2.sub.2N--CH.sub.2COCH.sub.2--CH.sub.2CO--OR.sup.1 (I) wherein, R.sup.1 is alkyl; and each R.sup.2 is independently hydrogen or alkyl; wherein each alkyl of R.sup.1 and R.sup.2 is optionally substituted by hydroxy, alkoxy, acyloxy, alkoxycarbonyloxy, amino, aryl, oxo or fluoro groups and is optionally interrupted by oxygen atoms; or a pharmaceutically acceptable salt thereof, and (b) one or more fatty substances.

30. The composition of claim 29, wherein the composition is in the form of a tablet or capsule suitable for oral administration.

31. The composition of claim 29, wherein the composition is in the form of a solution suitable for oral or rectal administration.

32. The composition of claim 31, wherein the composition comprises an aqueous carrier.

33. The composition of claim 29, claim 30, claim 31, or claim 32, wherein, in the compound of formula (I), R.sup.1 represents an unsubstituted alkyl group and each R.sup.2 is hydrogen.

34. The composition of claim 33 wherein the compound of formula (I) is ALA-methyl ester, ALA-ethyl ester, ALA-propyl ester, or ALA-hexyl ester.

35. The composition of claim 34, wherein the compound of formula (I) is ALA-hexyl ester.

36. The composition of claim 35, wherein the compound in the composition is the hydrochloride salt of ALA-hexyl ester.

37. The composition of claim 29, wherein the concentration of the compound in the composition is 10-50% (w/w).

38. The composition of claim 37, wherein the concentration of the compound is 15-30% (w/w).
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