US 2008/0287487 A1Published application

Muscarinic Acetylcholine Receptor Antagonists

OwnerAnthony William James Cooper, Dramane I. Laine +2inventors

InventorsAnthony William James Cooper, Dramane I. Laine, Michael R. Palovich, Sonia M. Thomas

Life of this patent

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Abstract

Muscarinic Acetylcholine Receptor Antagonists and methods of using them are provided.

Claims11

Dependent claims

A compound according to formula (I) as indicated below

wherein:
Y is selected from the group consisting of
R1 and R2 are, independently, selected from the group consisting of a bond, hydrogen, and C1-4 alkyl;
R3, R4, R5 and R6 are, independently, selected from the group consisting of hydrogen, halogen, nitro, cyano, C1-C10 alkyl, C2-10 alkenyl, C1-10 alkoxy, halosubstituted C1-10 alkoxy, (CR8R8)qORa, hydroxy, hydroxy substituted C1-4 alkyl, (CR8R8)qNR10R11, (CR8R8)qNC(O)R9, and (CR8R8)qC(O)NR10R11;
or two of either R3, R4, R5 or R6 moieties together may form a 5 to 6 membered saturated or unsaturated ring;
and wherein the alkyl, aryl, arylalkyl, heteroaryl, heteroalkyl, heterocyclic or heterocyclicalkyl groups may be optionally substituted;
R12, R13 and R14 are independently selected from the group consisting of hydrogen, halogen, nitro, cyano, C1-4 alkyl, C2-4 alkenyl, C1-4 alkoxy, halosubstituted C1-4 alkoxy, (CR8R8)pORa, hydroxy, hydroxy substituted C1-4 alkyl, (CR8R8)pNR10R11, (CR8R8)pNC(O)R9, and (CR8R8)pC(O)NR10R11;
or two of either R12, R13 or R14 moieties together may form a 5 to 6 membered saturated or unsaturated ring;
and wherein the alkyl, aryl, arylalkyl, heteroaryl, heteroalkyl, heterocyclic, or heterocyclicalkyl groups may be optionally substituted;
R7 is selected from the group consisting of hydrogen, and C1-4 alkyl;
R8 is hydrogen or C1-4 alkyl;
R9 is selected from the group consisting of hydrogen, optionally substituted C1-4 alkyl, and optionally substituted aryl;
R10 and R11 are, independently, selected from the group consisting of hydrogen, optionally substituted C1-4 alkyl, optionally substituted aryl, optionally substituted aryl C1-4 alkyl, optionally substituted heteroaryl, optionally substituted aryl C 1-4 alkyl, optionally substituted heteroaryl, optionally substituted heteroaryl C 1-4 alkyl, heterocyclic, and heterocyclic C1-4 alkyl;
or R10 and R11 together with the nitrogen to which they are attached form a 5 to 7 membered ring which may optionally comprise an additional heteroatom selected from O, N and S;
Ra is selected from the group consisting of hydrogen, alkyl, aryl, aryl C1-4 alkyl, heteroaryl, heteroaryl C1-4 alkyl, heterocyclic and a heterocyclic C1-4 alkyl moiety, all of which moieties may be optionally substituted;
q is 0, or an integer having a value of 1 to 10;
p is 0, or an integer having a value of 1 to 4;
n is 0 or 1;
X- is a physiologically acceptable anion, such as chloride, bromide, iodide, hydroxide, sulfate, nitrate, phosphate, acetate, trifluoroacetate, fumarate, citrate, tartrate, oxalate, succinate, mandelate, methanesulfonate and p-toluenesulfonate.

16 more elements

4 A compound according to claim 1 herein below

(3-endo)-3-[({[4-fluoro-2-(3-thienyl)phenyl]amino}carbonyl)oxy]-8,8-dimethyl-8-azoniabicyclo[3.2.1]octane bromide;
(3-endo)-8,8-dimethyl-3-[({[2-(3-thienyl)phenyl]amino}carbonyl)oxy]-8-azoniabicyclo[3.2.1]octane bromide;
(3-endo)-3-[({[2-fluoro-6-(3-thienyl)phenyl]amino}carbonyl)oxy]-8,8-dimethyl-8-azoniabicyclo[3.2.1]octane bromide;
(3-endo)-3-[({[4-fluoro-2-(2-thienyl)phenyl]amino}carbonyl)oxy]-8,8-dimethyl-8-azoniabicyclo[3.2.1]octane bromide;
(3-endo)-8,8-dimethyl-3-[({[5-methyl-2-(3-thienyl)phenyl]amino}carbonyl)oxy]-8-azoniabicyclo[3.2.1]octane bromide;
(3endo)-8,8-dimethyl-3-[({[4-methyl-2-(3-thienyl)phenyl]amino}carbonyl)oxy]-8-azoniabicyclo[3.2.1]octane bromide;
(3-endo)-3-[({[5-fluoro-2-(3-thienyl)phenyl]amino}carbonyl)oxy]-8,8-dimethyl-8-azoniabicyclo[3.2.1]octane bromide;
(3-endo)-8,8-dimethyl-3-[({[2-(2-thienyl)phenyl]amino}carbonyl)oxy]-8-azoniabicyclo[3.2.1]octane bromide;
(3-endo)-3-[({[4-chloro-2-(2-thienyl)phenyl]amino}carbonyl)oxy]-8,8-dimethyl-8-azoniabicyclo[3.2.1]octane bromide;
(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl[2-(3-thienyl)phenyl]carbamate;
(3-endo)-8,8-dimethyl-3-[({[5-methyl-2-(2-thienyl)phenyl]amino}carbonyl)oxy]-8-azoniabicyclo[3.2.1]octane bromide;
(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl[4-fluoro-2-(3-thienyl)phenyl]carbamate;
(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl[2-fluoro-6-(3-thienyl)phenyl]carbamate;
(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl[5-methyl-2-(3-thienyl)phenyl]carbamate;
(3-endo)-8,8-dimethyl-3-[({[4-methyl-2-(2-thienyl)phenyl]amino}carbonyl)oxy]-8-azoniabicyclo[3.2.1]octane bromide;
(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl[4-chloro-2-(3-thienyl)phenyl]carbamate;
(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl[4-methyl-2-(3-thienyl)phenyl]carbamate;
(3-endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl[5-fluoro-2-(3-thienyl)phenyl]carbamate;
(3-endo)-3-[({[3-fluoro-2-(3-thienyl)phenyl]amino}carbonyl)oxy]-8,8-dimethyl-8-azoniabicyclo[3.2.1]octane bromide;
(3-endo)-8-azabicyclo [3.2.1]oct-3-ylmethyl[4-fluoro-2-(3-thienyl)phenyl]carbamate;
(3-endo)-3-{[({[4-fluoro-2-(3-thienyl)phenyl]amino}carbonyl)oxy]methyl}-8,8-dimethyl-8-azoniabicyclo[3.2.1]octane trifluoroacetate;
(3-endo)-8-azabicyclo [3.2.1]oct-3-ylmethyl[5-methyl-2-(3-thienyl)phenyl]carbamate trifluoroacetate;
(3-endo)-8-azabicyclo[3.2.1]oct-3-ylmethyl[5-fluoro-2-(3-thienyl)phenyl]carbamate trifluoroacetate;
and
(3-endo)-8-azabicyclo [3.2.1]oct-3-ylmethyl[2-(3-thienyl)phenyl]carbamate.

22 more elements

Dependencies are inferred from the claim text.

Facts

Application: 11/570,981Filed 30 Jun 2005
Priority: 30 Jun 2004
Published: 20 Nov 2008
Term ends: Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07D 451/02
Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring…:…
A61P 11/00
Drugs for disorders of the respiratory system
A61P 11/02
Drugs for disorders of the respiratory system: nasal agents, e.g. decongestants
A61P 11/06
Drugs for disorders of the respiratory system: antiasthmatics

Family

Application60/584,011Us provisional application · filed 30 Jun 2004
US 2008/0287487 A1This patent

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

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A compound according to formula (I) as indicated below

wherein:
Y is selected from the group consisting of
R1 and R2 are, independently, selected from the group consisting of a bond, hydrogen, and C1-4 alkyl;
R3, R4, R5 and R6 are, independently, selected from the group consisting of hydrogen, halogen, nitro, cyano, C1-C10 alkyl, C2-10 alkenyl, C1-10 alkoxy, halosubstituted C1-10 alkoxy, (CR8R8)qORa, hydroxy, hydroxy substituted C1-4 alkyl, (CR8R8)qNR10R11, (CR8R8)qNC(O)R9, and (CR8R8)qC(O)NR10R11;
or two of either R3, R4, R5 or R6 moieties together may form a 5 to 6 membered saturated or unsaturated ring;
and wherein the alkyl, aryl, arylalkyl, heteroaryl, heteroalkyl, heterocyclic or heterocyclicalkyl groups may be optionally substituted;
R12, R13 and R14 are independently selected from the group consisting of hydrogen, halogen, nitro, cyano, C1-4 alkyl, C2-4 alkenyl, C1-4 alkoxy, halosubstituted C1-4 alkoxy, (CR8R8)pORa, hydroxy, hydroxy substituted C1-4 alkyl, (CR8R8)pNR10R11, (CR8R8)pNC(O)R9, and (CR8R8)pC(O)NR10R11;
or two of either R12, R13 or R14 moieties together may form a 5 to 6 membered saturated or unsaturated ring;
and wherein the alkyl, aryl, arylalkyl, heteroaryl, heteroalkyl, heterocyclic, or heterocyclicalkyl groups may be optionally substituted;
R7 is selected from the group consisting of hydrogen, and C1-4 alkyl;
R8 is hydrogen or C1-4 alkyl;
R9 is selected from the group consisting of hydrogen, optionally substituted C1-4 alkyl, and optionally substituted aryl;
R10 and R11 are, independently, selected from the group consisting of hydrogen, optionally substituted C1-4 alkyl, optionally substituted aryl, optionally substituted aryl C1-4 alkyl, optionally substituted heteroaryl, optionally substituted aryl C 1-4 alkyl, optionally substituted heteroaryl, optionally substituted heteroaryl C 1-4 alkyl, heterocyclic, and heterocyclic C1-4 alkyl;
or R10 and R11 together with the nitrogen to which they are attached form a 5 to 7 membered ring which may optionally comprise an additional heteroatom selected from O, N and S;
Ra is selected from the group consisting of hydrogen, alkyl, aryl, aryl C1-4 alkyl, heteroaryl, heteroaryl C1-4 alkyl, heterocyclic and a heterocyclic C1-4 alkyl moiety, all of which moieties may be optionally substituted;
q is 0, or an integer having a value of 1 to 10;
p is 0, or an integer having a value of 1 to 4;
n is 0 or 1;
X- is a physiologically acceptable anion, such as chloride, bromide, iodide, hydroxide, sulfate, nitrate, phosphate, acetate, trifluoroacetate, fumarate, citrate, tartrate, oxalate, succinate, mandelate, methanesulfonate and p-toluenesulfonate.

16 more elements

Facts

Application

11/570,981Filed 30 Jun 2005

Priority

30 Jun 2004

Published

20 Nov 2008

Term ends

Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07D 451/02
Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring…:…
A61P 11/00
Drugs for disorders of the respiratory system
A61P 11/02
Drugs for disorders of the respiratory system: nasal agents, e.g. decongestants
A61P 11/06
Drugs for disorders of the respiratory system: antiasthmatics