# US 7,410,996 B2 · 3-aryloxy/thio-2,3-substituted propanamines and their use in inhibiting serotonin and norepinephrine reuptake

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- Number: US 7,410,996 B2
- Document ID: US7410996B2
- Status: Granted
- Kind: B2
- Application number: 10/533,328
- Filed: 2003-10-24
- Published: 2006-08-03
- Granted: 2008-08-12
- Earliest claimed: 2002-11-05
- Assignees: Eli Lilly and Company
- Inventors: Serge Louis Boulet; Sandra Ann Filla; Peter Thaddeus Gallagher; Kevin John Hudziak; Anette Margareta Johansson; Rushad E. Karanjawala; John Joseph Masters; Victor Giulio Matassa; Brian Michael Mathes; Richard Edmund Rathmell; Maria Ann Whatton; Chad Nolan Wolfe
- Web page: https://patentgrep.com/patent/US7410996B2

## CPC

- C07D 275/04: condensed with carbocyclic rings or ring systems
- A61P 25/06: Antimigraine agents
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A61P 25/24: Antidepressants
- C07C 217/16: the six-membered aromatic ring or condensed ring system containing that ring not being further substituted
- C07C 217/30: having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
- C07C 217/48: the carbon skeleton being unsaturated and containing rings
- C07C 323/32: having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
- C07D 307/86: with an oxygen atom directly attached in position 7
- C07D 333/54: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D 333/62: with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D 475/04: with a nitrogen atom directly attached in position 2
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS

## Abstract

There is provided a compound of formula (I) wherein A is selected from —O— and —S—; X is selected from phenyl optionally substituted with up to 5 substituents each independently selected from halo, C1-C4 alkyl and C1-C4 alkoxy, thienyl optionally substituted with up to 3 substituents each independently selected from halo and C1-C4 alkyl, and C2-C8 alkyl, C2-C8 alkenyl, C3-C8 cycloalkyl and C4-C8 cycloalkylalkyl, each of which may be optionally substituted with up to 3 substituents each independently selected from halo, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl-S(O)n— where n is 0, 1 or 2, —CF3, —CN and —CONH2; Y is selected from phenyl, naphthyl, dihydrobenzothienyl, benzothiazolyl, benzoisothiazolyl, quinolyl, isoquinolyl, naphthyridyl, thienopyridyl, indanyl, 1,3-benzodioxolyl, benzothienyl, indolyl and benzofuranyl, each of which may be optionally substituted with up to 4 or, where possible, up to 5 substituents each independently selected from halo, C1-C4 alkyl, C1-C4 alkoxy, C1-C4 alkyl-S(O)n— where n is 0, 1 or 2, nitro, acetyl, —CF3, —SCF3 and cyano; and when Y is indolyl it may be substituted or further substituted by an N-substituent selected from C1-C4 alkyl; Z is selected from OR3 or F, wherein R3 is selected from H, C1-C6 alkyl and phenyl C1-C6 alkyl; R1 and R2 are each independently H or C1-C4 alkyl; and pharmaceutically acceptable salts thereof with the proviso that when Y is optionally substituted phenyl or optionally substituted 1,3-benzodioxolyl and Z is OR3 and X is optionally substituted phenyl then A is —S—.

## Claims

### Claim 1

A compound of formula I:
wherein
X is phenyl optionally substituted with fluorine
Y is benzothienyl, optionally substituted with fluorine
Z is selected from OH or F,
R1 and R2 are each independently H or C1-C4 alkyl; or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

A compound as claimed in claim 1, wherein one of R1 and R2 is H and the other is methyl.

### Claim 3 (depends on 1)

A pharmaceutical composition comprising a compound of formula I or a pharmaceutically acceptable salt thereof, as defined in claim 1, together with a pharmaceutically acceptable diluent or carrier.