# US 2016/0251306 A1 · Dimethylbenzoic acid compounds

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- Number: US 2016/0251306 A1
- Document ID: US20160251306A1
- Status: Published application
- Kind: A1
- Application number: 15/030,891
- Filed: 2014-12-11
- Published: 2016-09-01
- Earliest claimed: 2013-12-17
- Assignees: Eli Lilly and Company
- Applicants: Eli Lilly and Company
- Inventors: Maria Jesus Blanco-Pillado; Peter Rudolph Manninen; Matthew Allen Schiffler; Tatiana Natali Vetman; Alan M Warshawsky; Jeremy Schulenburg York
- Web page: https://patentgrep.com/patent/US20160251306A1

## CPC

- C07C 235/84: with the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- C07C 233/81: having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C 235/42: having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
- C07D 213/81: Amides; Imides
- C07D 215/52: with aryl radicals attached in position 2
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 405/04: directly linked by a ring-member-to-ring-member bond
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention provides a compound of the Formula I: wherein A is: and W, Y, X, R1, R2, R3, and R4 are as defined herein, or a pharmaceutically acceptable salt thereof, for use as an inhibitor of the EP4 receptor.

## Claims

### Claim 1

A compound of the formula:
wherein A is:
W is CH or N;
Y is CH or N;
X is CH or N;
R1 is CH3, CF3, or F;
R2 is H, F, Cl, CH3, CF3, CH2OH, CH2CH2OH, CH2OCH3, OCH3, OCF3, or CN;
R3 is H or F; or
R2 and R3 together are a OCH2O group attached to vicinal carbon atoms;
R4 is H, Cl, or CH2OH;
or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

The compound or salt according to claim 1 of the formula:

### Claim 3 (depends on 2)

The compound or salt according to claim 2 of the formula:

### Claim 4 (depends on 3)

The compound or salt according to claim 3 wherein A is:

### Claim 5 (depends on 4)

The compound or salt according to claim 4 wherein R1 is CH3.

### Claim 6 (depends on 5)

The compound or salt according to claim 5 wherein R3 is H.

### Claim 7 (depends on 6)

The compound or salt according to claim 6 wherein R2 is CH2OH, CH2CH2OH, or OCH3.

### Claim 8 (depends on 7)

The compound or salt according to claim 7 wherein R2 is CH2OH.

### Claim 9 (depends on 5)

The compound or salt according to claim 5 wherein R2 and R3 together are a OCH2O group attached to vicinal carbon atoms.

### Claim 10 (depends on 4)

The compound or salt according to claim 4 wherein R4 is Cl.

### Claim 11 (depends on 1)

The compounds or salts thereof according to claim 1 which are:
3-[[6-(1,3-benzodioxol-5-yl)-3-methyl-pyridine-2-carbonyl]amino]-2,4-dimethyl-benzoic acid;
3-[[6-[3-(hydroxymethyl)phenyl]-3-methyl-pyridine-2-carbonyl]amino]-2,4-dimethyl-benzoic acid; and
3-[[3-(3-chlorophenyl)naphthalene-1-carbonyl]amino]-2,4-dimethyl-benzoic acid.

### Claim 12 (depends on 1)

A method of treating osteoarthritis in a patient, comprising administering to a patient in need of such treatment an effective amount of a compound, or pharmaceutically acceptable salt thereof, according to claim 1.

### Claim 13 (depends on 1)

A method of treating rheumatoid arthritis in a patient, comprising administering to a patient in need of such treatment an effective amount of a compound or pharmaceutically acceptable salt thereof, according to claim 1.

### Claim 14 (depends on 1)

A method of treating pain associated with osteoarthritis or rheumatoid arthritis in a patient, comprising administering to a patient in need of such treatment an effective amount of a compound or a pharmaceutically acceptable salt thereof, according to claim 1.

### Claim 15

(canceled)

### Claim 16

(canceled)

### Claim 17

(canceled)

### Claim 18

(canceled)

### Claim 19 (depends on 1)

A pharmaceutical composition, comprising a compound or a pharmaceutically acceptable salt thereof according to claim 1 with one or more pharmaceutically acceptable carriers, diluents, or excipients.