US 7,009,051 B2Granted

4-(2-pyridyl) piperazines having 5HT7 receptor agonist activity

AssigneePfizer Inc.

InventorsWillard M. Welch, Vinod Parikh

Life of this patent

Estimating the term…

Abstract

The present invention relates to compounds of the formula I wherein R1, R2, R3, X and Y are defined as in the specification. Those compounds are 5HT7 partial agonists and are useful in the treatment of several disorders of the central nervous system.

Claims1

Dependent claims

A compound selected from the following compounds and their pharmaceutically acceptable salts:

1-[6-(Pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
3-{4-[6-(Pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazin-1-yl}-propan-1-ol;
1-Methyl-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-Ethyl-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-Benzyl-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-Propyl-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-(2-Methoxy-ethyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-Benzo[1,3]dioxol-5-ylmethyl-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-(2-Phenoxy-ethyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-(3-Phenoxy-propyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-(3-Phenyl-propyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-Butyl-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
3-{4-[6-(Pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazin-1-yl}-propionitrile-;
4-{4-[6-(Pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazin-1-yl}-butyronitrile;
1-(3-Methyl-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-(3-Chloro-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
3-{4-[6-(Pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazin-1-ylmethyl}-benzonitrile;
2-{4-[6-(Pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazin-1-ylmethyl}-benzonitrile;
4-{4-[6-(Pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazin-1-ylmethyl}-benzonitrile;
1-(3-Fluoro-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin--2-yl]-piperazine;
1-(4-Fluoro-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2- -yl]-piperazine;
1-(3-Methoxy-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2- -yl-piperazine;
1-(2-Chloro-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-y-1]-piperazine;
1-(4-tert-butyl-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-(2-Fluoro-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2- -yl]-piperazine;
1-(2-Bromo-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-y-1]-piperazine;
1-Isopropyl-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-Cyclopropyl-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-(1-Methyl-hexyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-[6-(2-Methyl-pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
4-(6-Piperazin-1-yl-pyridin-2-yloxymethyl)-quinoline;
1-[6-(3-Methyl-pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-[6-(2-Phenyl-pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-[6-(2,6-Dimethyl-pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
and
1-(4-Fluoro-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine.

33 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/617,967Filed 10 Jul 2003 · continuation
Priority: 2 May 2001
Published: US 2004/0014769 A122 Jan 2004
Granted: 7 Mar 2006
Term ends: Not estimatedThe source records don’t support an estimate.

Classification12 codes

C07D 213/74
Nitrogen atoms: amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
A61P 1/14
Drugs for disorders of the alimentary tract or the digestive system: prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics,…
A61P 13/02
Drugs for disorders of the urinary system: of urine or of the urinary tract, e.g. urine acidifiers
A61P 15/00
Drugs for genital or sexual disorders

Family

Application60/288,178Us provisional application · filed 2 May 2001
Application60/289,466Us provisional application · filed 8 May 2001
Application10/075,910Parent of this continuation · filed 13 Feb 2002
US 2004/0014769 A1Pre-grant publication · published 22 Jan 2004
US 2003/0008880 A1Published application
US 7,009,051 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

A compound selected from the following compounds and their pharmaceutically acceptable salts:

1-[6-(Pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
3-{4-[6-(Pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazin-1-yl}-propan-1-ol;
1-Methyl-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-Ethyl-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-Benzyl-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-Propyl-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-(2-Methoxy-ethyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-Benzo[1,3]dioxol-5-ylmethyl-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-(2-Phenoxy-ethyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-(3-Phenoxy-propyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-(3-Phenyl-propyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-Butyl-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
3-{4-[6-(Pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazin-1-yl}-propionitrile-;
4-{4-[6-(Pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazin-1-yl}-butyronitrile;
1-(3-Methyl-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-(3-Chloro-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
3-{4-[6-(Pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazin-1-ylmethyl}-benzonitrile;
2-{4-[6-(Pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazin-1-ylmethyl}-benzonitrile;
4-{4-[6-(Pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazin-1-ylmethyl}-benzonitrile;
1-(3-Fluoro-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin--2-yl]-piperazine;
1-(4-Fluoro-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2- -yl]-piperazine;
1-(3-Methoxy-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2- -yl-piperazine;
1-(2-Chloro-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-y-1]-piperazine;
1-(4-tert-butyl-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-(2-Fluoro-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2- -yl]-piperazine;
1-(2-Bromo-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-y-1]-piperazine;
1-Isopropyl-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-Cyclopropyl-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-(1-Methyl-hexyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-[6-(2-Methyl-pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
4-(6-Piperazin-1-yl-pyridin-2-yloxymethyl)-quinoline;
1-[6-(3-Methyl-pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-[6-(2-Phenyl-pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
1-[6-(2,6-Dimethyl-pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine;
and
1-(4-Fluoro-benzyl)-4-[6-(pyridin-4-ylmethoxy)-pyridin-2-yl]-piperazine.

33 more elements

Facts

Application

10/617,967Filed 10 Jul 2003 · continuation

Priority

2 May 2001

Published

US 2004/0014769 A122 Jan 2004

Granted

7 Mar 2006

Term ends

Not estimatedThe source records don’t support an estimate.

Classification12 codes

C07D 213/74
Nitrogen atoms: amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
A61P 1/14
Drugs for disorders of the alimentary tract or the digestive system: prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics,…
A61P 13/02
Drugs for disorders of the urinary system: of urine or of the urinary tract, e.g. urine acidifiers
A61P 15/00
Drugs for genital or sexual disorders

Family

Application60/288,178Us provisional application · filed 2 May 2001

Application60/289,466Us provisional application · filed 8 May 2001

Application10/075,910Parent of this continuation · filed 13 Feb 2002

US 2004/0014769 A1Pre-grant publication · published 22 Jan 2004

US 2003/0008880 A1Published application

US 7,009,051 B2This patent

From the US filing history. Foreign family members aren’t listed.