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US 8,557,552 B2Granted
Selective neuronal nitric oxide synthase inhibitors
AssigneeNorthwestern University
InventorsRichard B. Silverman, Haitao Ji, He Huang
Life of this patent
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Abstract
Compounds and related methods for selective inhibition of neuronal nitric oxide synthase over inducible and endothelial isoforms, such compounds as can provide reduced cationic character and enhanced bioavailability.
Claims30
A nitric oxide synthase inhibitor compound of a formula
- wherein n is selected from 0 and 1;
- Y is selected from CH2, O, NH, CH2O, CH2NH, CH2CH2 and CH═CH moieties;
- X is selected from N and CH;
- and R1 and R2 are independently selected from H, amono, methyl, methoxy, fluoro, chloro,and mono-, di- and trifluoromethyl, and mono-, di, and trichloromethyl substituents, and combinations thereof, or a salt thereof.
1 more element
A nitric oxide synthase inhibitor compound of a formula
- wherein Y is selected from CH2CH2 and CH═CH moieties;
- and R1 and R2 are independently selected from H, Cl and F, or a salt thereof.
A compound selected from
- 6-(((3R,4R)-4-((5-(3-chloro-5-fluorophenyl)pentyl)oxy)pyrrolidin-3-yl)methyl)-4-methylpyridin-2-amine (HH002);
- and
- 6-(((3R,4R)-4-(((E)-5-(3-fluorophenyl)pent-4-en-1-yl)oxy)pyrrolidin-3-yl)methyl)-4-methylpyridin-2-amine (HH003).
A nitric oxide synthase inhibitor compound of a formula
- wherein Y is selected from CH2CH2 and CH═CH moieties;
- R3 is selected from H and CH3;
- and R4 is selected from H and NH2, or a salt thereof.
A compound selected from
- 4-methyl-6-(((3R,4R)-4-((5-(pyridin-2-yl)pentyl)oxy)pyrrolidin-3-yl)methyl)pyridin-2-amine;
- 4-methyl-6-(((3R,4R)-4-((5-(4-methylpyridin-2-yl)pentyl)oxy)pyrrolidin-3-yl)methyl)pyridin-2-amine ;
- 6-(((3R,4R)-4-((5-(3-aminophenyl)pentyl)oxy)pyrrolidin-3-yl)methyl)-4-methylpyridin-2-amine;
- and
- 6-(((3R,4R)-4-((5-(3-amino-5-methylphenyl)pentyl)oxy)pyrrolidin-3-yl)methyl)-4-methylpyridin-2-amine.
2 more elements
A nitric oxide synthase inhibitor compound of a formula
- wherein Ar is selected from naphthalenylene and isoquinolinylene moieties;
- X is selected from CH and N;
- R1 is selected from H and CH3;
- and R2 is independently selected from H and NH2, and or salt thereof.
1 more element
A compound selected from
- 4-(((3R,4R)-4-((6-amino-4-methylpyridin-2-yl)methyl)pyrrolidin-3-yl)oxy)-N-(pyridin-2-yl)isoquinolin-7-amine;
- and
- 4-methyl-6-(((3R,4R)-4-((6-(pyridin-2-ylamino)naphthalen-1-yl)oxy)pyrrolidin-3-yl)methyl)pyridin-2-amine.
Dependencies are inferred from the claim text.