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Details for Patent: 9,134,328

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Details for Patent: 9,134,328

Title:Methods of using benzothiazole derivative compounds and compositions
Abstract: This invention provides benzothiazole derivative compounds, compositions comprising such compounds, methods of preparing such compounds, and methods of using such compounds for detecting amyloid deposit(s) and for diagnosing a disease, disorder or condition characterized by amyloid deposit(s).
Inventor(s): Klunk; William E. (Pittsburgh, PA), Mathis, Jr.; Chester A. (Pittsburgh, PA), Wang; Yanming (Beachwood, OH)
Assignee: University of Pittsburgh--Of the Commonwealth System of Higher Education (Pittsburgh, PA)
Filing Date:Apr 07, 2014
Application Number:14/246,890
Claims:1. A method for distinguishing an Alzheimer's diseased brain from a normal brain comprising: (i) obtaining tissues from the cerebellum and another area of the same brain, of a normal mammal and of a mammal suspected of having Alzheimer's disease; (ii) contacting the tissues with a compound of formula I; (iii) quantifying the amyloid bound to the compound; (iv) calculating the ratio of (a) the amount of amyloid in the area of the brain other than the cerebellum to (b) the amount of amyloid in the cerebellum; and (v) comparing the ratio for a normal mammal with the ratio for a mammal suspected of having Alzheimer's disease, wherein the compound of formula I is represented by formula I ##STR00010## or a pharmaceutically acceptable salt of the compound, wherein: R.sup.1 is hydrogen, --OH, --NO.sub.2, --CN, --COOR, --OCH.sub.2OR, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy, or halo; R is C.sub.1-C.sub.6 alkyl; R.sup.2 is a non-radioactive halo or a radioactive halo; R.sup.3 is hydrogen, C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl or C.sub.2-C.sub.6 alkynyl; and R.sup.4 is C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl or C.sub.2-C.sub.6 alkynyl, wherein when R.sup.2 is a non-radioactive halo, the alkyl, alkenyl or alkynyl of R.sup.4 comprises a radioactive carbon or .sup.3H, or is substituted with a radioactive halo.

2. The method of claim 1, wherein: (a) R.sup.1 is hydrogen, --OH, --CN, C.sub.1-C.sub.6 alkyl, C.sub.7-C.sub.6 alkenyl, C.sub.2-C.sub.6 alkynyl, C.sub.1-C.sub.6 alkoxy or halo; and (b) R.sup.4 is C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl or C.sub.2-C.sub.6 alkynyl, wherein the alkyl, alkenyl or alkynyl comprises a radioactive carbon.

3. The method of claim 2, wherein: (a) R.sup.1 is hydrogen, --OH, --CN, --OCH.sub.3, --CH.sub.3, or --Br; and (b) R.sup.3 is hydrogen or --CH.sub.3; and (c) R.sup.4 is --.sup.11CH.sub.3 or --.sup.14CH.sub.3.

4. The method of claim 3, wherein R.sup.4 is --.sup.14CH.sub.3.

5. The method of claim 1, wherein: (a) R.sup.2 is a non-radioactive halo or a radioactive halo, wherein the halo is iodo; and (b) R.sup.4 is C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl or C.sub.2-C.sub.6 alkynyl, wherein the alkyl, alkenyl or alkynyl comprises a radioactive carbon when R.sup.2 is a non-radioactive halo.

6. The method of claim 5, wherein: (a) R is --CH.sub.3; and (b) the radioactive carbon in R.sup.4 is .sup.11C or .sup.14C.

7. The method of claim 6 wherein the radioactive carbon in R.sup.4 is .sup.14C.

8. The method of claim 6 wherein: (a) R.sup.1 is --OH or C.sub.1-C.sub.6 alkoxy; (b) R.sup.2 is a radioiodine; (c) R.sup.3 is hydrogen or C.sub.1-C.sub.6 alkyl; and (d) R.sup.4 is C.sub.1-C.sub.6 alkyl.

9. The method of claim 6, wherein: (a) R.sup.1 is --OH; (b) R.sup.2 is --.sup.123I or --.sup.125I; and (c) R.sup.3 is hydrogen.

10. The method of claim 1, wherein R.sup.2 is a radiofluoro.

11. The method of claim 10, wherein: (a) R.sup.1 is --OH or C.sub.1-C.sub.6 alkoxy; (b) R.sup.2 is .sup.18F; (c) R.sup.3 is hydrogen or C.sub.1-C.sub.6 alkyl; and (d) R.sup.4 is C.sub.1-C.sub.6 alkyl.

12. The method of claim 11, wherein: (a) R.sup.1 is --OH; (b) R.sup.3 is hydrogen; and (c) R.sup.4 is --CH.sub.3.

13. The method of claim 1, wherein R.sup.4 is C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl or C.sub.2-C.sub.6 alkynyl, wherein the alkyl, alkenyl or alkynyl comprises a radioactive carbon or .sup.3H.

14. The method of claim 1, wherein, R.sup.4 is C.sub.1-C.sub.6 alkyl, C.sub.2-C.sub.6 alkenyl, or C.sub.2-C.sub.6 alkynyl, wherein the alkyl, alkenyl or alkynyl is substituted with a radioactive halo.

15. The method of claim 14, wherein: (a) R.sup.1 is --OH or C.sub.1-C.sub.6 alkoxy; (b) R.sup.2 is hydrogen; (c) R.sup.3 is hydrogen or C.sub.1-C.sub.6 alkyl; and (d) R.sup.4 is C.sub.1-C.sub.6 alkyl substituted with .sup.18F.

16. The method of claim 15, wherein: (a) R.sup.1 is --OH; (b) R.sup.3 is hydrogen; and (c) R.sup.4 is --CH.sub.2CH.sub.2CH.sub.2.sup.18F.

17. The method of claim 1, wherein the compound is selected from the group consisting of: [N-Methyl-.sup.11C]2-(4'-Dimethylaminophenyl)-6-methoxy-benzothiazole; 2-(3'-.sup.125I-iodo-4'-amino-phenyl)-benzothiazol-6-ol; 2-(3-[.sup.18F]-fluoro-4-methylamino-phenyl)-benzothiazol-6-ol; and 2-[4-(3-.sup.18F-fluoro-propylamino)-phenyl]benzothiazol-6-ol.

18. The method of claim 1, wherein the mammal is a human.

19. The method of claim 1, wherein the tissues from at least one mammal are obtained by a biopsy.

20. The method of claim 19, wherein the biopsy tissue is formalin-fixed, fresh-frozen, homogenized, or any combination thereof.

21. The method of claim 1, wherein a diagnosis of Alzheimer's disease is made if the ratio for a mammal suspected of having Alzheimer's disease is above 90% of the ratio for a normal mammal.
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