Last Updated: June 23, 2026

Claims for Patent: 9,040,518

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Summary for Patent: 9,040,518

Title:	Chemical compounds
Abstract:	Compounds of Formula I and methods for treating metabolic disorders are disclosed.
Inventor(s):	Christopher Joseph Aquino, Jon Loren Collins, David John Cowan, Yulin Wu
Assignee:	GlaxoSmithKline LLC
Application Number:	US13/640,166
Patent Claims:	1. A compound of Formula I wherein R1 is H, Cl, Br, N(CH3)2, or methoxy; R2 is H or OH; each R3 is independently C1-6alkyl; X is CH2, C(O), or CH═CH; Q is C0-6alkyl; R4 is OH, SO3H, CO2H, PO3H2, CONR5R5, NR5R5; or NHC(O)CH2NR5R5; each R5 is independently H, OH, C1-6alkyl, C0-6alkylCO2H, C0-6 alkylSO3H, C0-6alkylPO3H2, C(O)C0-6alkylCO2H, C(O)C0-6alkylSO3H, C(O)C0-6alkylPO3H2, or CH(R7)C0-6alkyCO2H; and R7 is C0-6alkylCO2H, C0-6alkylOH, C0-6alkylSO3H, or C0-6alkylPO3H2. 2. A compound according to claim 1 wherein R1 is methoxy. 3. A compound according to claim 2 wherein R2 is H. 4. A compound according to claim 3 wherein X is CH2. 5. A compound according to claim 1 wherein X is C(O). 6. A compound according to claim 1 wherein Q is C0-2alkyl. 7. A compound according to claim 4 wherein Q is absent. 8. A compound according to claim 7 wherein each R3 is independently C2-4 alkyl. 9. A compound according to claim 8 wherein each R3 is independently ethyl or n-butyl. 10. A compound according to claim 1 wherein R4 is PO3H2. 11. A compound according to claim 9 wherein R4 is NR5R5. 12. A compound according to claim 11 wherein one R5 is H and the other is OH, methyl, C1-4alkylCO2H, C0-2 alkylSO3H, C1-2alkylPO3H2, C(O)CO2H, C(O)C1-2alkylSO3H, C(O)C1-2alkylPO3H2, or CH(R7)C0-1alkyCO2H. 13. A compound according to claim 12 wherein one R5 is H and the other is CH2CO2H, CH2SO3H, CH2CH2SO3H, or CH(R7)C0-1alkyCO2H. 14. A compound according to claim 13 wherein R7 is C0-1alkylCO2H or C0-2alkylSO3H. 15. The compound 16. The compound 17. The compound of claim 16 wherein said compound is crystalline. 18. A pharmaceutically acceptable salt of a compound according to claim 1. 19. A pharmaceutical composition comprising a compound according to claim 16. 20. A method for treating diabetes mellitus (Type I or Type II) or obesity, in a human comprising administration of a composition according to claim 19. 21. The method of claim 20 wherein said method is for treating Type II diabetes mellitus. 22. The method of claim 21 wherein said method further comprises administration of metformin.

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