Granted Patent B2

US 8,901,087 · App. 13/883,811 · Granted Dec 2, 2014

Abstract

Claims (277)

1. A compound of Formula (I) or a pharmaceutically acceptable salt thereof:

wherein:

each R is independently H or C(O)CH 3 ;

R 1 and R 2 are independently selected from the group consisting of: H, C 1-6 alkyl, C 2-6 alkenyl, C 1-6 alkoxy, —(CH 2 ) n -cyclopropyl and —(CH 2 ) n -cyclobutyl wherein n is 0, 1, 2, 3 or 4; or R 1 and R 2 may be joined together with the nitrogen atom to which they are attached to form azetidine, pyrrolidine, piperidine or isoxazolidine, said C 1-6 alkyl, C 2-6 alkenyl, C 1-6 alkoxy, —(CH 2 ) n -cyclopropyl, —(CH 2 ) n -cyclobutyl, azetidine, pyrrolidine, piperidine and isoxazolidine optionally substituted from one up to the maximum number of substituents with fluoro, hydroxy and methyl;

R 3 is selected from the group consisting of: C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl, C 3-6 cycloalkyl, aryl and heteroaryl, each optionally substituted from one up to the maximum number of substituents with fluoro and OH;

R 4 is selected from the group consisting of: H, F, C 1-8 alkyl, C 2-8 alkenyl and C 2-8 alkynyl, each excluding hydrogen optionally substituted from one up to the maximum number of substituents with fluoro and OH; or R 3 and R 4 and the carbon atom to which they are attached may join together to form vinyl or a 3 to 7-membered carbocyclic or heterocyclic ring, said 3 to 7-membered carbocyclic or heterocyclic ring optionally containing a double bond and optionally substituted from one up to the maximum number of substituents with fluoro and OH; and

R 5 is selected from H, F, OH and OC(O)CH 3 ;

with the proviso that when R 4 is F then R 5 is other than OH and OC(O)CH 3 .

2. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein R 1 and R 2 are independently selected from the group consisting of: H, C 1-6 alkyl, C 1-6 alkoxy, —(CH 2 ) n -cyclopropyl and —(CH 2 ) n -cyclobutyl wherein n is 0, 1, 2, 3 or 4; or R 1 and R 2 may be joined together with the nitrogen atom to which they are attached to form azetidine, pyrrolidine or piperidine, said C 1-6 alkyl, C 1-6 alkoxy, —(CH 2 ) n -cyclopropyl, —(CH 2 ) n -cyclobutyl, azetidine, pyrrolidine and piperidine optionally substituted from one up to the maximum number of substituents with fluoro and methyl.

3. The compound according to claim 2 of Formula (Ia) or a pharmaceutically acceptable salt thereof:

4. The compound according to claim 3 or a pharmaceutically acceptable salt thereof, wherein:

R 1 and R 2 are independently C 1-4 alkyl;

R 3 is C 1-6 alkyl;

R 4 is selected from the group consisting of: H and C 1-6 alkyl; and

R 5 is OH.

5. The compound according to claim 4 or a pharmaceutically acceptable salt thereof, wherein:

R 1 and R 2 are independently methyl or ethyl;

R 3 is methyl or ethyl; and

R 4 is selected from the group consisting of: H, methyl and ethyl.

6. The compound according to claim 3 or a pharmaceutically acceptable salt thereof, wherein R 3 and R 4 and the carbon atom to which they are attached may join together to form a 3 to 7-membered carbocyclic or heterocyclic ring, said 3 to 7-membered carbocyclic or heterocyclic ring optionally containing a double bond and optionally substituted from one up to the maximum number of substituents with fluoro and OH.

7. The compound according to claim 3 or a pharmaceutically acceptable salt thereof, wherein:

R 1 and R 2 are independently selected from the group consisting of: H, C 1-6 alkyl and cyclopropylmethyl; or R 1 and R 2 may be joined together with the nitrogen atom to which they are attached to form azetidine or pyrrolidine, said C 1-6 alkyl, cyclopropylmethyl, azetidine or pyrrolidine optionally substituted with 1 to 3 substituents selected from fluoro and methyl;

R 3 is selected from the group consisting of: C 1-8 alkyl, C 2-8 alkenyl, C 2-8 alkynyl and C 3-6 cycloalkyl, each optionally substituted with 1 to 3 substituents selected from fluoro and OH; and

R 4 is selected from the group consisting of: H, F, C 1-8 alkyl, C 2-8 alkenyl and C 2-8 alkynyl, each excluding hydrogen optionally substituted with 1 to 3 substituents selected from fluoro and OH; or R 3 and R 4 and the carbon atom to which they are attached may join together to form a 5-membered carbocyclic ring optionally containing a double bond and optionally substituted with 1 to 3 substituents selected from fluoro and OH.

8. The compound according to claim 3 or a pharmaceutically acceptable salt thereof, wherein R 3 is CF 3 and R 5 is OH.

9. A compound which is selected from the group consisting of:

(3aR,5R,6S,7R,7aR)-2-(Dimethylamino)-5-((S)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,6S,7R,7aR)-5-((S)-1-hydroxyethyl)-2-(propylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-(2-Hydroxypropan-2-yl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-(2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(Dimethylamino)-5-(2-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(Dimethylamino)-5-ethyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-vinyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-Ethyl-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(Dimethylamino)-5-((S)-1-fluoroethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-((S)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-(1,1-Difluoroethyl)-2-(dimethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxyethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1-hydroxyethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxypropyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1-hydroxypropyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-(1-hydroxy-2-methylpropyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-(cyclopropyl(hydroxy)methyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-(hydroxy(pyridin-3-yl)methyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-(hydroxy(phenyl)methyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1-hydroxyallyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxyallyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1-hydroxy-2-methylallyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1-hydroxybut-3-enyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxybut-3-enyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-((R)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-((S)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-cyclopropyl(hydroxy)methyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(1-hydroxy-2-methylpropyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(hydroxy(phenyl)methyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-((R)-1-hydroxyallyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-((S)-1-hydroxyallyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-((R)-1-hydroxy-2-methylallyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-((R)-1-hydroxybutyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-((S)-1-hydroxybutyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-((R)-1-hydroxypentyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-((S)-1-hydroxypentyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-((R)-1-hydroxybut-3-enyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-((S)-1-hydroxybut-3-enyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-(2-hydroxypropan-2-yl)-2-(propylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxyallyl)-2-(propylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1-hydroxybutyl)-2-(propylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxybutyl)-2-(propylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1-hydroxypentyl)-2-(propylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxypentyl)-2-(propylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-(1-hydroxypropyl)-2-(propylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1-hydroxybut-3-enyl)-2-(propylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxybut-3-enyl)-2-(propylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1-hydroxyethyl)-2-(methoxy(methyl)amino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxyethyl)-2-(methoxy(methyl)amino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(cyclopropylmethylamino)-5-((R)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(cyclopropylmethylamino)-5-((S)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethyl(methyl)amino)-5-((S)-1-hydroxybut-3-enyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethyl(methyl)amino)-5-((R)-1-hydroxybut-3-enyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(ethyl(methyl)amino)-5-(2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethyl(methyl)amino)-5-(1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethyl(methyl)amino)-5-((R)-1-hydroxypropyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethyl(methyl)amino)-5-(1-hydroxypropyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(ethyl(methyl)amino)-5-((R)-1-hydroxyallyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(ethyl(methyl)amino)-5-(1-hydroxyallyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-((S)-1-hydroxypropyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-((S)-1-hydroxyallyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-((R)-1-hydroxy-2-methylallyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-((S)-1-hydroxy-2-methylallyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-((R)-1-hydroxybut-3-enyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-((S)-1-hydroxybut-3-enyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-((R)-1-hydroxybutyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-((S)-1-hydroxybutyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-((R)-1-hydroxypentyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-((S)-1-hydroxypentyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-((S)-1-hydroxyhexyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-((R)-1-hydroxyheptyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-((S)-1-hydroxyheptyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(azetidin-1-yl)-5-((R)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(azetidin-1-yl)-5-((S)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(azetidin-1-yl)-5-(2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(azetidin-1-yl)-5-((S)-1-hydroxypropyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(azetidin-1-yl)-5-((R)-1-hydroxyallyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(azetidin-1-yl)-5-((S)-1-hydroxyallyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(azetidin-1-yl)-5-((R)-1-hydroxybut-3-enyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(azetidin-1-yl)-5-((S)-1-hydroxybut-3-enyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-(2-hydroxypropan-2-yl)-2-(methyl(propyl)amino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-(1-hydroxypropyl)-2-(methyl(propyl)amino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxyethyl)-2-(methyl(propyl)amino)-5,6,7,7a-tetrahydro-3 aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1-hydroxyallyl)-2-(methyl(propyl)amino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxyallyl)-2-(methyl(propyl)amino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1-hydroxybut-3-enyl)-2-(methyl(propyl)amino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxybut-3-enyl)-2-(methyl(propyl)amino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-(2-hydroxypropan-2-yl)-2-(pyrrolidin-1-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxyethyl)-2-(pyrrolidin-1-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1-hydroxypropyl)-2-(pyrrolidin-1-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxypropyl)-2-(pyrrolidin-1-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxyallyl)-2-(pyrrolidin-1-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(methylamino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(propylamino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(methoxy(methyl)amino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(methylamino)-5-((S)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(propylamino)-5-((S)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(methoxy(methyl)amino)-5-((S)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(ethylamino)-5-((S)-1-fluoroethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-((R)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-((S)-1-hydroxypropyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-((R)-1-hydroxypropyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-((S)-1-fluoroethyl)-2-(pyrrolidin-1-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1-hydroxybutyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxybutyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1-hydroxypentyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxypentyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1-hydroxyhexyl)-2-(methylamino)-5,6,7,7a-tetrahydropyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxyhexyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1-hydroxyethyl)-2-(propylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(cyclopropylmethylamino)-5-((S)-1-hydroxy-2-methylallyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(cyclopropylmethylamino)-5-((R)-1-hydroxypropyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(cyclopropylmethylamino)-5-((S)-1-hydroxypropyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(cyclopropylmethylamino)-5-((R)-1-hydroxybut-3-enyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(cyclopropylmethylamino)-5-(1-hydroxybut-3-enyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(cyclopropylmethylamino)-5-((S)-1-hydroxyallyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(2-cyclopropylethylamino)-5-((R)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(2-cyclopropylethylamino)-5-((S)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano

(3aR,5S,6S,7R,7aR)-2-(2-cyclopropylethylamino)-5-(2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethyl(methyl)amino)-5-((R)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethyl(methyl)amino)-5-((S)-1-hydroxybutyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethyl(methyl)amino)-5-((S)-1-hydroxypentyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-((R)-1-hydroxyhexyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxybutyl)-2-(pyrrolidin-1-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxypentyl)-2-(pyrrolidin-1-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-(1,1-difluoroethyl)-2-(methoxy(methyl)amino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-ethyl-2-(ethyl(methyl)amino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(azetidin-1-yl)-5-ethyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(azetidin-1-yl)-5-vinyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-ethyl-2-(propylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-ethyl-2-(ethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-vinyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-(1-hydroxycyclopentyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-(1-hydroxycyclopent-3-enyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-(2-fluoropropan-2-yl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(methylamino)-5-(prop-1-en-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(2-Fluoroethylamino)-5-((S)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(3-Fluoropropylamino)-5-((S)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-(3-Hydroxypropyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(Ethylamino)-5-(2-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-(2-hydroxyethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(Dimethylamino)-5-(2-fluoropropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-(1,1-Difluoroethyl)-2-(propylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-(1,1-difluoroethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-((S)-2,2-difluoro-1-hydroxyethyl)-2-(dimethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-((R)-2,2-difluoro-1-hydroxyethyl)-2-(dimethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1,2-dihydroxyethyl)-2-(dimethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1,2-dihydroxyethyl)-2-(dimethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-((S)-2-fluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-((R)-2-fluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-(2-fluoroethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-(2,2-difluoroethyl)-2-(dimethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-(2,2,2-trifluoroethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(methylamino)-5-((S)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(methylamino)-5-(1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(ethylamino)-5-((S)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(ethylamino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1-hydroxyethyl)-2-(2-hydroxyethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxyethyl)-2-(2-hydroxyethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-amino-5-[(1S)-2,2,2-trifluoro-1-hydroxyethyl]-3aH,5H,6H,7H,7aH-pyrano[3,2-d][1,3]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-amino-5-[(1R)-2,2,2-trifluoro-1-hydroxyethyl]-3aH,5H,6H,7H,7aH-pyrano[3,2-d][1,3]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(allylamino)-5-((S)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(allylamino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(allylamino)-5-((R)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(allylamino)-5-((S)-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(allylamino)-5-((S)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(allylamino)-5-(1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(2-hydroxyethylamino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(allylamino)-5-(2-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(allylamino)-5-(2,2-difluoroethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-amino-5-[(2S)-1,1,1-trifluoro-2-hydroxypropan-2-yl]-3aH,5H,6H,7H,7aH-pyrano[3,2-d][1,3]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-amino-5-[(2R)-1,1,1-trifluoro-2-hydroxypropan-2-yl]-3aH,5H,6H,7H,7aH-pyrano[3,2-d][1,3]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-amino-5-vinyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-amino-5-ethyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-((R)-1-fluoroethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-((S)-1-fluoroethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-((R)-1-fluoroethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(azetidin-1-yl)-5-((R)-1-fluoroethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-((S)-1,2,2,2-tetrafluoroethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-((S)-1-fluoroethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(azetidin-1-yl)-5-((S)-1-fluoroethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-((R)-1,2,2,2-tetrafluoroethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(azetidin-1-yl)-5-((R)-1,1,1-trifluoropropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(azetidin-1-yl)-5-((S)-1,1,1-trifluoropropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-((R)-1,1,1-trifluoropropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(dimethylamino)-5-((S)-1,1,1-trifluoropropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-((R)-2,2-difluoro-1-hydroxyethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-((S)-2-fluoro-1-hydroxyethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-5-((R)-2-fluoro-1-hydroxyethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-(2-fluoroethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-(2,2-difluoroethyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(methylamino)-5-(2,2,2-trifluoroethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(2,2,2-trifluoroethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(propylamino)-5-(2,2,2-trifluoroethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(azetidin-1-yl)-5-((S)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(azetidin-1-yl)-5-((R)1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-((S)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-((R)1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-((S)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(ethylamino)-5-((S)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(ethylamino)-5-((R)1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((R)-1-hydroxyethyl)-2-(isoxazolidin-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxyethyl)-2-(isoxazolidin-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-((S)-1-hydroxypropyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-5-((S)-1-hydroxyheptyl)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(ethyl(methyl)amino)-5-((S)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[1,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(ethyl(methyl)amino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(azetidin-1-yl)-5-((S)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(azetidin-1-yl)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(2-fluoroethylamino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(2-fluoroethylamino)-5-((S)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

(3aR,5R,6S,7R,7aR)-2-(methylamino)-5-((R)-1,1,1-trifluoropropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol; and

(3aR,5R,6S,7R,7aR)-2-(methylamino)-5-((S)-1,1,1-trifluoropropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol;

or a pharmaceutically acceptable salt of any of the foregoing compounds.

10. The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein: each R is H, R 5 is OH, R 3 is C 1-6 alkyl, optionally substituted from one up to the maximum number of substituents with fluoro and hydroxy, and R 4 is H.

11. The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein: each R is H, R 5 is H, R 3 is C 1-6 alkyl, optionally substituted from one up to the maximum number of substituents with fluoro and hydroxy, and R 4 is H or C 1-6 alkyl.

12. The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein R 1 is C 1-6 alkyl, optionally substituted from one up to the maximum number of substituents with hydroxy, and R 2 is H.

13. The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein R 1 is C 2-6alkenyl and R 2 is H.

14. The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein each R is H and R 5 is F.

15. A pharmaceutical composition comprising a compound according to claim 1 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

16. A method for treating a condition which is selected from the group consisting of: an inflammatory disease, an allergy, asthma, allergic rhinitis, hypersensitivity lung diseases, hypersensitivity pneumonitis, eosinophilic pneumonias, delayed-type hypersensitivity, atherosclerosis, interstitial lung disease (ILD), idiopathic pulmonary fibrosis, ILD associated with rheumatoid arthritis, systemic lupus erythematosus, ankylosing spondylitis, systemic sclerosis, Sjogren's syndrome, polymyositis or dermatomyositis, systemic anaphylaxis or hypersensitivity response, drug allergy, insect sting allergy, autoimmune disease, rheumatoid arthritis, psoriatic arthritis, multiple sclerosis, Guillain-Barré syndrome, systemic lupus erythematosus, myastenia gravis, glomerulonephritis, autoimmune thyroiditis, graft rejection, allograft rejection, graft-versus-host disease, inflammatory bowel disease, Crohn's disease, ulcerative colitis, spondyloarthropathy, scleroderma, psoriasis, T-cell mediated psoriasis, inflammatory dermatosis, dermatitis, eczema, atopic dermatitis, allergic contact dermatitis, urticaria, vasculitis, necrotizing, cutaneous, and hypersensitivity vasculitis, eosinphilic myotis, eosiniphilic fasciitis, solid organ transplant rejection, heart transplant rejection, lung transplant rejection, liver transplant rejection, kidney transplant rejection, pancreas transplant rejection, kidney allograft, lung allograft, epilepsy, pain, fibromyalgia, stroke, and neuroprotection in a subject in need thereof, the method comprising administering to the subject an effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

17. A method for treating a condition which is selected from the group consisting of a neurodegenerative disease, cancer and stress, in a subject in need thereof, the method comprising administering to the subject an effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

18. A method for treating a condition which is selected from the group consisting of: Alzheimer's disease, Amyotrophic lateral sclerosis (ALS), Amyotrophic lateral sclerosis with cognitive impairment (ALSci), Argyrophilic grain dementia, Bluit disease, Corticobasal degeneration (CBD), Dementia pugilistica, Diffuse neurofibrillary tangles with calcification, Down's syndrome, Familial British dementia, Familial Danish dementia, Frontotemporal dementia with parkinsonism linked to chromosome 17 (FTDP-17), Gerstmann-Straussler-Scheinker disease, Guadeloupean parkinsonism, Hallevorden-Spatz disease (neurodegeneration with brain iron accumulation type 1), Multiple system atrophy, Myotonic dystrophy, Niemann-Pick disease (type C), Pallido-ponto-nigral degeneration, Parkinsonism-dementia complex of Guam, Pick's disease (PiD), Post-encephalitic parkinsonism (PEP), Prion diseases (including Creutzfeldt-Jakob Disease (CJD), Variant Creutzfeldt-Jakob Disease (vCJD), Fatal Familial Insomnia, and Kuru), Progressive supercortical gliosis, Progressive supranuclear palsy (PSP), Richardson's syndrome, Subacute sclerosing panencephalitis, Tangle-only dementia, Huntington's disease, Parkinson's disease, Schizophrenia, Mild Cognitive Impairment (MCI), Neuropathy (including peripheral neuropathy, autonomic neuropathy, neuritis, and diabetic neuropathy), and Glaucoma in a subject in need thereof, the method comprising administering to the subject an effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

19. A method for treating a condition which is selected from the group consisting of: ischemia; hemorrhage; hypovolemic shock; myocardial infarction; an interventional cardiology procedure; cardiac bypass surgery; fibrinolytic therapy; angioplasty; and stent placement in a subject in need thereof, the method comprising administering to the subject an effective amount of a compound according to claim 1 , or a pharmaceutically acceptable salt thereof.

20. The compound of claim 9 which is (3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-(2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol, or a pharmaceutically acceptable salt thereof.

21. The compound of claim 9 which is (3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-(2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol.

22. The compound of claim 9 which is (3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-(2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol in the form of a pharmaceutically acceptable salt thereof.

23. The compound of claim 9 which is (3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol, or a pharmaceutically acceptable salt thereof.

24. The compound of claim 9 which is (3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol.

25. The compound of claim 9 which is (3aR,5S,6S,7R,7aR)-2-(dimethylamino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol in the form of a pharmaceutically acceptable salt thereof.

26. The compound of claim 9 which is (3aR,5S,6S,7R,7aR)-2-(methylamino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol, or a pharmaceutically acceptable salt thereof.

27. The compound of claim 9 which is (3aR,5S,6S,7R,7aR)-2-(methylamino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol.

28. The compound of claim 9 which is (3aR,5S,6S,7R,7aR)-2-(methylamino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol in the form of a pharmaceutically acceptable salt thereof.

29. The compound of claim 9 which is (3aR,5S,6S,7R,7aR)-2-(methylamino)-5-((S)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol, or a pharmaceutically acceptable salt thereof.

30. The compound of claim 9 which is (3aR,5S,6S,7R,7aR)-2-(methylamino)-5-((S)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol.

31. The compound of claim 9 which is (3aR,5S,6S,7R,7aR)-2-(methylamino)-5-((S)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol in the form of a pharmaceutically acceptable salt thereof.

32. The compound of claim 9 which is (3aR,5S,6S,7R,7aR)-2-(methylamino)-5-((R)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol, or a pharmaceutically acceptable salt thereof.

33. The compound of claim 9 which is (3aR,5S,6S,7R,7aR)-2-(methylamino)-5-((R)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol.

34. The compound of claim 9 which is (3aR,5S,6S,7R,7aR)-2-(methylamino)-5-((R)-1,1,1-trifluoro-2-hydroxypropan-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol in the form of a pharmaceutically acceptable salt thereof.

35. The compound of claim 9 which is (3aR,5S,6S,7R,7aR)-2-(ethylamino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol, or a pharmaceutically acceptable salt thereof.

36. The compound of claim 9 which is (3aR,5S,6S,7R,7aR)-2-(ethylamino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol.

37. The compound of claim 9 which is (3aR,5S,6S,7R,7aR)-2-(ethylamino)-5-((R)-2,2,2-trifluoro-1-hydroxyethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol in the form of a pharmaceutically acceptable salt thereof.

38. A pharmaceutical composition comprising the compound of claim 20 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

39. A pharmaceutical composition comprising the compound of claim 23 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

40. A pharmaceutical composition comprising the compound of claim 26 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

41. A pharmaceutical composition comprising the compound of claim 29 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

42. A pharmaceutical composition comprising the compound of claim 32 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

43. A pharmaceutical composition comprising the compound of claim 35 or a pharmaceutically acceptable salt thereof and a pharmaceutically acceptable carrier.

Assignments (14)