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US 7,598,267 B2Granted
Muscarinic acetylcholine receptor antagonists
AssigneeGlaxo Group Limited
InventorsDramane I. Laine, Brent W. McCleland, Christopher E. Neipp, Michael R. Palovich
Life of this patent
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Abstract
Muscarinic Acetylcholine Receptor Antagonists and methods of using them are provided.
Claims42
A compound of formula (I) as indicated below
- wherein:
- R1 is selected from hydrogen, C1-15 alkyl, halosubstituted C1-15 alkyl, aryl C1-15 alkyl, C1-15 alkyl cycloalkyl, cycloalkyl, C2-15 alkenyl, hydroxy substituted C1-15 alkyl, C1-15 alkyl aryl, (CR7R7)qORa, (CR7R7)qNRaRa, (CR7R7)qNC(O)Ra, (CR7R7)qC(O)NRaRa, (CR7R7)qC(O)Ra, (CR7R7)qC(O)ORa, or (CR7R7)qOC (O)Ra;
- or
- R1 is:
- R2 and R3 are independently selected, from the group consisting of aryl, aryl C1-4 alkyl, C1-4 alkyl aryl, heteroaryl, heteroaryl C1-4 alkyl, C1-4 alkyl heteroaryl, heterocyclic, C1-4 alkyl heterocyclic and a heterocyclic C1-4 alkyl moiety;
- Ra is selected from the group consisting of hydrogen, C1-15 alkyl, C1-15 alkoxy, aryl, aryl C1-15 alkyl, heteroaryl, heteroaryl C1-15 alkyl, heterocyclic and a heterocyclic C1-15 alkyl;
- q is 0 or an integer having a value of 1 to 15;
- n is an integer having a value of 1 to 14;
- m is an integer having a value of 1 to 15;
- p is an integer having a value of 1 to 4;
- X, Y, Z and W are, independently, selected from the group consisting of hydrogen, C1-4 alkyl, C1-4 alkyl aryl, halosubstituted C1-4 alkyl, and hydroxy substituted C1-4 alkyl;
- V is selected from the group consisting of O, S, and NRb;
- Rb is selected from the group consisting of hydrogen, C1-4 alkyl and aryl C1-4 alkyl;
- R7 is selected from the group consisting of hydrogen, C1-4 alkyl, halosubstituted C1-4 alkyl, and hydroxy substituted C1-4 alkyl;
- and
- X— is a physiologically acceptable anion.
13 more elements
A compound according to formula (II) herein below:
- wherein:
- R1 is selected from the group consisting of hydrogen, C1-10 alkyl, halosubstituted C1-10 alkyl, C1-10 alkyl aryl, C1-10 alkyl cycloalkyl, cycloalkyl, hydroxy substituted C1-10 alkyl, C2-5 alkenyl, and (CR7R7)qORa;
- R2 and R3 are, independently, selected from the group consisting of:
- F, G, H, K and L are independently selected from the group consisting of hydrogen, halogen, cyano, C1-4 alkyl, halosubstituted C1-4 alkyl, hydoxy substituted C1-4 alkyl, and C1-4 alkoxy;
- Ra is selected from the group consisting of hydrogen, C1-10 alkyl, C1-10 alkoxy, and C1-10 alkyl aryl;
- or
- Ra is:
- wherein:
- M, N, O, P and Q are, independently, selected from the group consisting of hydrogen, halogen, cyano, nitro, and amino, C1-4 alkyl, halosubstituted C1-4 alkyl, hydroxy substituted C1-4 alkyl, and C1-4 alkoxy;
- or two of either M, N, O, P and Q moieties, together, form a 5 to 6 membered saturated or unsaturated ring;
- q is 0 or an integer having a value of 1 to 10;
- n is an integer having a value of 1 to 9;
- m is an integer having a value of 1 to 10;
- p is an integer having a value of 1 to 4;
- V is selected from the group consisting of O, S, NH, and NHRb;
- Rb is selected from the group consisting of hydrogen, C1-4 alkyl, and aryl C1-4 alkyl;
- R7 is hydrogen or, C1-4 alkyl;
- and
- X— is a physiologically acceptable anion, selected from the group consisting of chloride, bromide, iodide, hydroxide, sulfate, nitrate, phosphate, acetate, trifluoroacetate, fumarate, citrate, tartrate, oxalate, succinate, mandelate, methanesulfonate and p-toluenesulfonate.
16 more elements
The compound which is 4-[cyano(diphenyl)methyl]-1-[2-(methyloxy)ethyl]-1-azoniabicyclo[2.2.2]octane bromide.
Dependencies are inferred from the claim text.