# US 7,608,629 B2 · (Piperidinyloxy)phenyl, (piperidinyloxy)pyridinyl, (piperidinylsulfanyl)phenyl and (piperidinylsulfanyl)pyridinyl compounds as 5-HT1F agonists

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- Number: US 7,608,629 B2
- Document ID: US7608629B2
- Status: Granted
- Kind: B2
- Application number: 10/552,131
- Filed: 2004-04-14
- Published: 2006-09-21
- Granted: 2009-10-27
- Earliest claimed: 2003-04-18
- Assignees: Eli Lilly and Company
- Inventors: Maria-Jesus Blanco-Pillado; Dana Rae Benesh; Sandra Ann Filla; Kevin John Hudziak; Brian Michael Mathes; Daniel Timothy Kohlman; Bai-Ping Ying; Deyi Zhang; Yao-Chang Xu
- Web page: https://patentgrep.com/patent/US7608629B2

## CPC

- C07D 401/12: linked by a chain containing hetero atoms as chain links
- A61P 1/02: Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- A61P 1/14: Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- A61P 3/04: Anorexiants; Antiobesity agents
- A61P 5/24: of the sex hormones
- A61P 15/00: Drugs for genital or sexual disorders (for disorders of sex hormones A61P5/24); Contraceptives
- A61P 15/08: for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
- A61P 15/10: for impotence
- A61P 17/02: for treating wounds, ulcers, burns, scars, keloids, or the like
- A61P 19/00: Drugs for skeletal disorders
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/04: Centrally acting analgesics, e.g. opioids
- A61P 25/06: Antimigraine agents
- A61P 25/14: for treating abnormal movements, e.g. chorea, dyskinesia
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/20: Hypnotics; Sedatives
- A61P 25/22: Anxiolytics
- A61P 25/24: Antidepressants
- 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 25/32: Alcohol-abuse
- A61P 25/34: Tobacco-abuse
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 211/44: attached in position 4
- C07D 211/46: having a hydrogen atom as the second substituent in position 4
- C07D 211/54: Sulfur atoms
- C07D 401/14: containing three or more hetero rings
- C07D 409/12: linked by a chain containing hetero atoms as chain links
- C07D 409/14: containing three or more hetero rings
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

The present invention relates to compounds of formula 1: and pharmaceutically acceptable acid addition sails thereof. The compounds of the present invention are useful for activating 5-HT1F receptors, inhibiting neuronal protein extravasation, and for the treatment or preverition of migraine in mammals, particularly humans.

## Claims

### Claim 1

A compound of formula I:
or a pharmaceutically acceptable acid addition salt thereof, where;
Q is oxygen or sulfur;
X is —C(R4c)═ or —N═;
R1 is mono- di-, or tri-substituted phenyl wherein the substitutions are independently selected from halo, C1-C2 alkoxy, trifluoromethyl, trifluoromethoxy, and trifluoroethoxy;
R2 is hydrogen or methyl;
R3 hydrogen;
R4a and R4b are hydrogen
When X is —C(R4c)═, R4c is hydrogen
R5 hydrogen; and
R6 is hydrogen.

### Claim 2 (depends on 1)

A composition comprising a compound according to claim 1 and a pharmaceutical carrier, diluent, or excipient.

### Claim 3

A method for the treatment of migraine in a mammal comprising administering to a mammal in need of such treatment or prevention an effective amount of a compound of formula I:
or a pharmaceutically acceptable acid addition salt thereof, where;
Q is oxygen or sulfur;
X is —C(R4c)═ or —N═;
R1 mono- di-, or tri-substituted phenyl wherein the substitutions are independently selected from halo, C1-C2 alkoxy, trifluoromethyl, trifluoromethoxy, and trifluoroethoxy;
R2 is hydrogen or methyl;
R3 hydrogen;
R4a and R4b are hydrogen;
When X is —C(R4c)═, R4c is hydrogen;
R5 hydrogen; and
R6 is hydrogen.

### Claim 4 (depends on 3)

The method according to claim 3 wherein the mammal is a human.

### Claim 5

A compound of formula I:
or a pharmaceutically acceptable acid addition salt thereof, where;
Q is oxygen or sulfur;
X is —C(H)═ or —N═;
R1 is a substituted or unsubstituted heterocycle wherein the heterocycle is selected from the group consisting of pyridinyl and thiophenyl;
R2 is hydrogen or methyl;
R3 is hydrogen;
R4a and R4b are hydrogen
R5 hydrogen; and
R6 is hydrogen.

### Claim 6 (depends on 5)

A composition comprising a compound according to claim 5 and a pharmaceutical carrier, diluents, or excipient.

### Claim 7

A method for the treatment of migraine in a mammal comprising administering to a mammal in need of such treatment or prevention an effective amount of a compound of formula I;
or a pharmaceutically acceptable acid addition salt thereof, where;
Q is oxygen or sulfur;
X is —C(H)═ or —N═;
R1 is a substituted or unsubstituted heterocycle wherein the heterocycle is selected from the group consisting of pyridinyl and thiophenyl;
R2 is hydrogen or methyl;
R3 hydrogen;
R4a and R4b are hydrogen
R5 hydrogen; and
R6 is hydrogen.

### Claim 8 (depends on 7)

The method according to claim 7 wherein the mammal is human.