# US 8,772,291 B2 · Multicyclic compounds and methods of their use

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- Number: US 8,772,291 B2
- Document ID: US8772291B2
- Status: Granted
- Kind: B2
- Application number: 12/633,453
- Filed: 2009-12-08
- Published: 2010-04-01
- Granted: 2014-07-08
- Earliest claimed: 2005-05-13
- Assignees: Lexicon Pharmaceuticals, Inc.
- Applicants: Joseph Barbosa; Li Dong; Cynthia Anne Fink; Jiancheng Wang; G. Gregory Zipp
- Inventors: Joseph Barbosa; Li Dong; Cynthia Anne Fink; Jiancheng Wang; G. Gregory Zipp
- Web page: https://patentgrep.com/patent/US8772291B2

## CPC

- C07D 239/42: One nitrogen atom (nitro radicals C07D239/30)
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/28: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 277/42: Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
- C07D 401/04: directly linked by a ring-member-to-ring-member bond
- C07D 401/12: linked by a chain containing hetero atoms as chain links
- C07D 401/14: containing three or more hetero rings
- C07D 403/04: directly linked by a ring-member-to-ring-member bond
- C07D 417/04: directly linked by a ring-member-to-ring-member bond
- C07D 451/02: containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
- C07D 471/08: Bridged systems
- C07D 487/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

This invention relates to multicyclic compounds, pharmaceutical compositions comprising them, and methods of their use in, for example, the treatment of cognitive disorders.

## Claims

### Claim 1

A compound of the formula
or a pharmaceutically acceptable salt thereof, wherein:
each of E1, E2 and E3 is independently N or CR2;
each of G1 and G2 is independently N or CR3;
each of R1, R2 and R3 is independently hydrogen, halogen, cyano, RA, ORA, C(O)RA, C(O)ORA, C(O)N(RARB), N(RARB), or SO2RA;
each R5 is independently halogen, cyano, RA, ORA, C(O)RA, C(O)ORA, C(O)N(RARB), N(RARB), or SO2RA;
each RA is independently hydrogen or optionally substituted alkyl, aryl, arylalkyl, alkylaryl, heterocycle, heterocycle-alkyl, or alkyl-heterocycle;
each RB is independently hydrogen or optionally substituted alkyl, aryl, arylalkyl, alkylaryl, heterocycle, heterocycle-alkyl, or alkyl-heterocycle; and
n is 0-5.

### Claim 2 (depends on 1)

The compound of claim 1, wherein G1 is N.

### Claim 3 (depends on 1)

The compound of claim 1, wherein G2 is N.

### Claim 4 (depends on 1)

The compound of claim 1, wherein G1 and G2 are both N.

### Claim 5 (depends on 1)

The compound of claim 1, wherein each R1 is hydrogen.

### Claim 6 (depends on 1)

The compound of claim 1, wherein E1 is CR2.

### Claim 7 (depends on 1)

The compound of claim 1, wherein E2 is CR2.

### Claim 8 (depends on 1)

The compound of claim 1, wherein E3 is CR2.

### Claim 9 (depends on 1)

The compound of claim 1, wherein E1, E2 and E3 are all CR2.

### Claim 10 (depends on 9)

The compound of claim 9, wherein E1, E2 and E3 are all CH.

### Claim 11 (depends on 10)

The compound of claim 10, wherein at least one R2 is halo.

### Claim 12 (depends on 11)

The compound of claim 11, wherein one of R2 is chloro.

### Claim 13 (depends on 1)

The compound of claim 1, wherein n is 0.

### Claim 14

A compound or a pharmaceutically acceptable salt thereof, wherein the compound is (3′-chlorobiphenyl-4-yl)(1-(pyrimidin-2-yl)piperidin-4-yl)methanone.

### Claim 15 (depends on 1)

A pharmaceutical composition comprising a compound of claim 1 and a pharmaceutically acceptable excipient.

### Claim 16 (depends on 15)

A capsule or tablet comprising the pharmaceutical composition of claim 15.

### Claim 17 (depends on 14)

A pharmaceutical composition comprising a compound of claim 14 and a pharmaceutically acceptable excipient.

### Claim 18 (depends on 17)

A capsule or tablet comprising the pharmaceutical composition of claim 17.