# US 7,410,982 B2 · Propanamine derivatives as serotonin and norepinephrine reuptake inhibitors

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- Number: US 7,410,982 B2
- Document ID: US7410982B2
- Status: Granted
- Kind: B2
- Application number: 10/532,765
- Filed: 2003-10-24
- Published: 2006-03-16
- 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; Brian Michael Mathes; Richard Edmund Rathmell; Maria Ann (nee Fagan) Whatton; Victor Matassa; Chad Nolan Wolfe
- Web page: https://patentgrep.com/patent/US7410982B2

## CPC

- C07D 275/04: condensed with carbocyclic rings or ring systems
- A61P 25/00: Drugs for disorders of the nervous system
- C07D 215/20: Oxygen atoms
- C07D 217/02: with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D 217/04: with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
- C07D 217/24: Oxygen atoms
- C07D 277/62: Benzothiazoles
- C07D 333/54: with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D 471/04: Ortho-condensed systems
- C07D 495/04: Ortho-condensed systems
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS

## Abstract

There is provided a heretoaryloxy/thio 3-substituted propanamine 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 dihydrobenzothienyl, benzothiazolyl, benzoisothiazolyl, quinolyl, isoquinolyl, naphthyridyl, and thienopyridyl, 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; Z is selected from H, OR3 or F, wherein R3 is selected from H, C1-C6 alkyl and phenyl C1C6 alkyl; R1 and R2 are each independently H or C1-C4 alkyl; and pharmaceutically acceptable salts thereof.

## Claims

### Claim 1

A compound of formula I:
where Y is thienopyridinyl; or a pharmaceutically acceptable salt thereof.

### Claim 2 (depends on 1)

A compound of claim 1, wherein the compound possesses the stereochemistry defined in formula II

### Claim 3 (depends on 1)

A compound claim 1, wherein the compound possesses the stereochemistry defined in formula III

### Claim 4 (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.