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Last Updated: January 18, 2020

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Claims for Patent: 9,375,496

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Summary for Patent: 9,375,496
Title:Halogenated compounds for cancer imaging and treatment and methods for their use
Abstract: Compounds having a structure of Formula I: ##STR00001## or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are as defined herein, and wherein the compound comprises at least one F, Cl, Br, I or .sup.123I moiety, are provided. Uses of such compounds for imaging diagnostics in cancer and therapeutics methods for treatment of subjects in need thereof, including prostate cancer as well as methods and intermediates for preparing such compounds are also provided.
Inventor(s): Andersen; Raymond John (Vancouver, CA), Banuelos; Carmen Adriana (Richmond, CA), Garcia Fernandez; Javier (Colunga, ES), Imamura; Yusuke (Chiba, JP), Kunzhong; Jian (Vancouver, CA), Mawji; Nasrin R. (Burnaby, CA), Sadar; Marianne Dorothy (West Vancouver, CA), Wang; Jun (Surrey, CA), Tien; Amy (Hsing Chen) (Vancouver, CA)
Assignee: British Columbia Cancer Agency Branch (CA) The University of British Columbia (CA)
Application Number:14/481,727
Patent Claims:1. A compound having a structure of Formula I: ##STR00068## or a pharmaceutically acceptable salt, tautomer or stereoisomer thereof, wherein: R.sup.1 and R.sup.2 are each independently H or C.sub.1-C.sub.10 alkyl, or R.sup.1 and R.sup.2, together with the carbon atom to which they are bound, are taken together to form a carbocyclic or heterocyclic ring; R.sup.3 is H or C.sub.1-C.sub.10 alkylcarboyl; R.sup.4 and R.sup.5 are each independently H, C.sub.1-C.sub.10 alkyl or C.sub.1-C.sub.10 alkylcarbonyl; and X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are each independently H, F, Cl, Br, I or .sup.123I, wherein at least one of X.sup.1, X.sup.2, X.sup.3 or X.sup.4 is .sup.123I.

2. The compound of claim 1, wherein the compound has one of the following structures (Ia), (Ib), (Ic), (Id), (Ie), (If), (Ig) or (Ih): ##STR00069## ##STR00070##

3. The compound of claim 1, wherein three of X.sup.1, X.sup.2, X.sup.3 and X.sup.4 are H, and the remaining X.sup.1, X.sup.2, X.sup.3 or X.sup.4 is .sup.123I.

4. The compound of claim 1, wherein X.sup.1 is F, Cl, Br or I or .sup.123I.

5. The compound of claim 1, wherein X.sup.3 is F, Cl, Br or I or .sup.123I.

6. The compound of claim 1, wherein R.sup.1 and R.sup.2 are each C.sub.1-C.sub.10 alkyl.

7. The compound of claim 6, wherein C.sub.1-C.sub.10 alkyl is methyl.

8. The compound of claim 1, wherein at least one of R.sup.3, R.sup.4 or R.sup.5 is H.

9. The compound of claim 1, wherein R.sup.3, R.sup.4 and R.sup.5 are each H.

10. The compound of claim 1, wherein at least one of R.sup.4 or R.sup.5 is C.sub.1-C.sub.10 alkyl.

11. The compound of claim 1, wherein R.sup.4 and R.sup.5 are each C.sub.1-C.sub.10 alkyl.

12. The compound of claim 11, wherein C.sub.1-C.sub.10 alkyl is methyl, isopropyl or n-butyl.

13. The compound of claim 1, wherein at least one of R.sup.3, R.sup.4 or R.sup.5 is C.sub.1-C.sub.10 alkylcarbonyl.

14. The compound of claim 1, wherein R.sup.3, R.sup.4 and R.sup.5 are each C.sub.1-C.sub.10 alkylcarbonyl.

15. The compound of claim 14, wherein C.sub.1-C.sub.10 alkylcarbonyl is methyl carbonyl.

16. The compound of claim 1, wherein the compound has one of the following Structures: ##STR00071## ##STR00072## ##STR00073## or a pharmaceutically acceptable salt or stereoisomer thereof.

17. A pharmaceutical composition comprising a compound of claim 1, and a pharmaceutically acceptable carrier.

18. A method of imaging cancer, the method comprising administering a compound of claim 1 to a subject and detecting the presence or absence of cancer by use of SPECT or PET.

19. The method of claim 18, wherein the method identifies the presence or absence of a tumor.

20. The method of claim 18, wherein the method identifies the location of a tumor.

21. The method of claim 18, wherein the cancer is prostate cancer.

22. A pharmaceutical composition comprising a compound of claim 1, an additional therapeutic agent and a pharmaceutically acceptable carrier, wherein the additional therapeutic agent is enzalutamide, galeterone, ODM-201, ARN-509, abiraterone, bicalutamide, nilutamide, flutamide, cyproterone acetate, docetaxel, Bevacizumab (Avastin), OSU-HDAC42, VITAXIN, sunitumib, ZD-4054, Cabazitaxel (XRP-6258), MDX-010 (Ipilimumab), OGX 427, OGX 011, finasteride, dutasteride, turosteride, bexlosteride, izonsteride, FCE 28260, SKF105,111 or related compounds thereof.

23. A method of imaging cancer, the method comprising administering the pharmaceutical composition of claim 17 to a subject and detecting the presence or absence of cancer by use of SPECT or PET.

Details for Patent 9,375,496

Applicant Tradename Biologic Ingredient Dosage Form BLA Number Approval Date Patent No. Assignee Estimated Patent Expiration Status Orphan Source
Genentech AVASTIN bevacizumab VIAL; INTRAVENOUS 125085 001 2004-02-26   Start Trial British Columbia Cancer Agency Branch (CA) The University of British Columbia (CA) 2033-09-09 RX Orphan search
Genentech AVASTIN bevacizumab VIAL; INTRAVENOUS 125085 002 2004-02-26   Start Trial British Columbia Cancer Agency Branch (CA) The University of British Columbia (CA) 2033-09-09 RX Orphan search
Bristol Myers Squibb YERVOY ipilimumab INJECTABLE; INJECTION 125377 001 2011-03-25   Start Trial British Columbia Cancer Agency Branch (CA) The University of British Columbia (CA) 2033-09-09 RX Orphan search
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Number >Approval Date >Patent No. >Assignee >Estimated Patent Expiration >Status >Orphan >Source

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