# US 9,040,518 B2 · Chemical compounds

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- Number: US 9,040,518 B2
- Document ID: US9040518B2
- Status: Granted
- Kind: B2
- Application number: 13/640,166
- Filed: 2011-04-27
- Published: 2013-01-31
- Granted: 2015-05-26
- Earliest claimed: 2010-04-27
- Assignees: GlaxoSmithKline LLC
- Applicants: Christopher Joseph Aquino; Jon Loren Collins; David John Cowan; Yulin Wu
- Inventors: Christopher Joseph Aquino; Jon Loren Collins; David John Cowan; Yulin Wu
- Web page: https://patentgrep.com/patent/US9040518B2

## CPC

- C07D 281/10: condensed with one six-membered ring
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 3/10: for hyperglycaemia, e.g. antidiabetics
- A61P 5/00: Drugs for disorders of the endocrine system
- C07D 417/06: linked by a carbon chain containing only aliphatic carbon atoms
- C07F 9/6541: condensed with carbocyclic rings or {carbocyclic} ring systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)

## Abstract

Compounds of Formula I and methods for treating metabolic disorders are disclosed.

## Claims

### Claim 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.

### Claim 2 (depends on 1)

A compound according to claim 1 wherein R1 is methoxy.

### Claim 3 (depends on 2)

A compound according to claim 2 wherein R2 is H.

### Claim 4 (depends on 3)

A compound according to claim 3 wherein X is CH2.

### Claim 5 (depends on 1)

A compound according to claim 1 wherein X is C(O).

### Claim 6 (depends on 1)

A compound according to claim 1 wherein Q is C0-2alkyl.

### Claim 7 (depends on 4)

A compound according to claim 4 wherein Q is absent.

### Claim 8 (depends on 7)

A compound according to claim 7 wherein each R3 is independently C2-4 alkyl.

### Claim 9 (depends on 8)

A compound according to claim 8 wherein each R3 is independently ethyl or n-butyl.

### Claim 10 (depends on 1)

A compound according to claim 1 wherein R4 is PO3H2.

### Claim 11 (depends on 9)

A compound according to claim 9 wherein R4 is NR5R5.

### Claim 12 (depends on 11)

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.

### Claim 13 (depends on 12)

A compound according to claim 12 wherein one R5 is H and the other is CH2CO2H, CH2SO3H, CH2CH2SO3H, or CH(R7)C0-1alkyCO2H.

### Claim 14 (depends on 13)

A compound according to claim 13 wherein R7 is C0-1alkylCO2H or C0-2alkylSO3H.

### Claim 15

The compound

### Claim 16

The compound

### Claim 17 (depends on 16)

The compound of claim 16 wherein said compound is crystalline.

### Claim 18 (depends on 1)

A pharmaceutically acceptable salt of a compound according to claim 1.

### Claim 19 (depends on 16)

A pharmaceutical composition comprising a compound according to claim 16.

### Claim 20 (depends on 19)

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.

### Claim 21 (depends on 20)

The method of claim 20 wherein said method is for treating Type II diabetes mellitus.

### Claim 22 (depends on 21)

The method of claim 21 wherein said method further comprises administration of metformin.