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Claims for Patent: 6,034,267

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Claims for Patent: 6,034,267

Title: Esters of 5-aminolevulinic acid as photosensitizing agents in photochemotherapy
Abstract:The invention provides a pharmaceutical compositions comprising a compound of formula I: wherein, R.sup.1 and R.sup.2 have any of the values defined in the specification; or a salt thereof; and a pharmaceutically acceptable carrier or excipient. The invention also provides a method for the diagnosis or photochemotherapeutic treatment of disorders or abnormalities of external or internal surfaces of the body using such compounds or salts.
Inventor(s): Gierskcky; Karl E. (Oslo, NO), Moan; Johan (Oslo, NO), Peng; Qian (Oslo, NO), Steen; Harald (Oslo, NO), Warloe; Trond (Oslo, NO), Bjorseth; Alf (Oslo, NO)
Assignee: PhotoCure AS (Olso, NO)
Application Number:08/913,257
Patent Claims: 1. A method for the diagnosis or photochemotherapeutic treatment of disorders or abnormalities of external or internal surfaces of the body, comprising:

i) administering to the sites of investigation or affected surfaces a composition comprising a compound of formula 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 salt thereof; and

ii) exposing said sites or surfaces to light.

2. The method of claim 1 wherein aryl is phenyl or a monocyclic 5-7 membered heteroaromatic.

3. The method of claim 1 wherein R.sup.1 represents an unsubstituted alkyl group and each R.sup.2 is hydrogen.

4. The method of claim 1 wherein R.sup.1 represents an unsubstituted alkyl group or each R.sup.2 is hydrogen.

5. The method of claim 1 wherein alkyl contains up to 10 carbon atoms.

6. The method of claim 1 wherein the compound is ALA-methyl ester, ALA-ethyl ester, ALA-propyl ester, ALA-hexyl ester, ALA-heptyl ester, or ALA-octyl ester; or a salt thereof.

7. The method of claim 1 wherein the light is in the wavelength region 500-700 nm.

8. A pharmaceutical composition comprising an effective diagnostic or therapeutic amount of a compound of formula 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; together with at least one pharmaceutical carrier or excipient.

9. The composition of claim 8 wherein the compound is ALA-methyl ester, ALA-ethyl ester, ALA-propyl ester, ALA-hexyl ester, ALA-heptyl ester, or ALA-octyl ester; or a pharmaceutically acceptable salt thereof.

10. The composition of claim 8 further comprising at least one surface-penetration assisting agent, and optionally one or more chelating agents.

11. The composition of claim 10 wherein the surface-penetration assisting agent is dimethyl sulfoxide.

12. The composition of claim 10 wherein the compound is ALA-methyl ester, ALA-ethyl ester, ALA-propyl ester, ALA-hexyl ester, ALA-heptyl ester, or ALA-octyl ester; or a pharmaceutically acceptable salt thereof.

13. A method for in vitro diagnosis of abnormalities or disorders by assaying a sample of body fluid or tissue of a patient, said method comprising:

i) admixing said body fluid or tissue with a compound of formula 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;

ii) exposing said mixture to light;

iii) ascertaining the level of fluorescence; and

iv) comparing the level of fluorescence to control levels.

14. The method of claim 13 wherein the compound is ALA-methyl ester, ALA-ethyl ester, ALA-propyl ester, ALA-hexyl ester, ALA-heptyl ester, or ALA-octyl ester; or a pharmaceutically acceptable salt thereof.

15. A kit for use in diagnosis or photochemotherapy of disorders or abnormalities of external or internal surfaces of the body comprising:

i) a first container containing a compound of formula 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;

ii) a second container containing at least one surface penetration assisting agent; and optionally

iii) one or more chelating agents contained either within said first container or in a third container.

16. The kit of claim 15 wherein the compound is ALA-methyl ester, ALA-ethyl ester, ALA-propyl ester, ALA-hexyl ester, ALA-heptyl ester, or ALA-octyl ester; or a phamaceutically acceptable salt thereof.
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