US 8,946,413 B2Granted

3-aminocyclopentanecarboxamides as chemokine receptor agonists

AssigneePfizer Inc.

InventorsRobert O. Hughes, Rajesh V. Devraj, Donald J. Rogier, John I. Trujillo, Steve R. Turner, Wei Huang

Life of this patent

Estimating the term…

Abstract

There is provided a compound of Formula I(a) or I(b): or a pharmaceutically acceptable salt thereof, wherein the various substitutents are defined herein.

Claims13

Dependent claims

A compound of Formula I(a) or I(b):

or a pharmaceutically acceptable salt thereof, wherein:
A is O or CF2;
W is CR13R14, C(O), CHOR15, CHF, or CF2;
R1 is H or (C1-C6)alkyl optionally substituted by 1-3 substituents selected from halo, OH, CO2H, CO2—(C1-C6)alkyl, or (C1-C3) alkoxy;
R2 and R3 are each, independently, H, (C1-C6)alkyl, (C1-C6) haloalkyl, halo, (C3-C6) cycloalkyl, CN, OH, OCOR12;
wherein said (C1-C6)alkyl is optionally substituted with one or more substituents selected from F, (C1-C3) alkoxy, OH, CN or CO2R12;
R8 and R9 are each, independently, H, (C1-C6)alkyl, (C1-C6)haloalkyl, (C3-C6)cycloalkyl, CN, OH, OCOR12;
wherein said (C1-C6)alkyl is optionally substituted with one or more substituents selected from F, (C1-C3) alkoxy, OH, CN or CO2R12;
R2 and R9, taken together may form a 5-8 membered ring;
R4 and R7, taken together may form a 5-8 membered ring;
R4 and R5 are each, independently, H, CN, (C1-C6)alkyl, halo, (C1-C3)alkoxy, (C1-C3)haloalkoxy, (C3-C6)cycloalkyl, OH, CO2R12, OCOR12, wherein said (C1-C6)alkyl is optionally substituted with one or more substituents selected from F, (C1-C3) alkoxy, OH or CO2R12;
R6 and R7 are each, independently, H, CN, (C1-C6)alkyl, halo, (C1-C3)alkoxy, (C1-C3)haloalkoxy, (C3-C6)cycloalkyl, OH, CO2R12, OCOR12, wherein said (C1-C6)alkyl is optionally substituted with one or more substituents selected from F, (C1-C3) alkoxy, OH or CO2R12;
or R2 and R3 together with the carbon atom to which they are attached form a 3-7 membered spirocyclyl group;
or R4 and R5 together with the carbon atom to which they are attached form a 3-7 membered spirocyclyl group;
or R3 and R4 together with the C atoms to which they are attached form a fused 3-7 membered cycloalkyl group or 3-7 membered heterocycloalkyl group;
R10 is (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)hydroxyalkyl, (C1-C6)alkoxy, (C3-C6)cycloalkyl, hydroxy(C3-C6)cycloalkyl, alkoxy cycloalkyl, OH, (C1-C5)heterocyclyl, amino, aryl or CN,
R11 is aryl or heteroaryl, said R11 optionally, independently substituted by one or more (C1-C6) alkyl, halo, (C1-C6)haloalky(C1-C3)alkoxy, OH, amino, C(O)NH2, NH2SO2, SF5, or CN;
R12 is H, (C1-C4)alkyl, or (C3-C6)cycloalkyl;
R13 is H, halo, (C1-C4)alkyl, (C1-C4)alkoxy, or OH;
R14 is H, halo, (C1-C4)alkyl, (C1-C4)alkoxy or OH;
and
R15 is H, (C1-C6)alkyl or (C3-C6)cycloalkyl.

19 more elements

A compound selected from the group consisting of:

1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-ethyl-3-({(1S,4S)-5-[4-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-ethyl-3-({(1S,4S)-5-[4-(trifluoromethyl)pyrimidin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-ethyl-3-({(1S,4S)-5-[6-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-ethyl-3-({(1S,4S)-5-[6-(trifluoromethyl)pyrazin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-ethyl-3-({(1S,4S)-5-[2-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-ethyl-3-({(1S,4S)-5-[6-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-ethyl-3-({(1S,4S)-5-[2-(trifluoromethyl)pyridin-4-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-ethyl-3-({(1S,4S)-5-[3-fluoro-4-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-methyl-3-({(1S,4S)-5-[4-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-methyl-3-({(1S,4S)-5-[6-(trifluoromethyl)pyrazin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-isopropyl-3-({(1S,4S)-5-[4-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-isopropyl-3-({(1S,4S)-5-[4-(trifluoromethyl)pyrimidin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-isopropyl-3-({(1S,4S)-5-[6-(trifluoromethyl)pyrazin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-isopropyl-3-({(1S,4S)-5-[2-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-isopropyl-3-({(1S,4S)-5-[6-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-isopropyl-3-({(1S,4S)-5-[2-(trifluoromethyl)pyridin-4-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-isopropyl-3-({(1S,4S)-5-[5-(trifluoromethyl)pyridazin-3-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-3-{[(1R,3S)-3-isopropyl-3-({(1S,4S)-5-[2,6-bis(trifluoromethyl)pyridin-4-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)-3-isopropylcyclopentyl]amino}-2,3-dideoxy-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-({(1S,4S)-5-[3-fluoro-4-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)-3-isopropylcyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-isopropyl-3-({(1S,4S)-5-[6-methyl-4-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-isopropyl-3-({(1S,4S)-5-[3-(trifluoromethyl)phenyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-({(1S,4S)-5-[3-fluoro-5-(trifluoromethyl)phenyl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)-3-isopropylcyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-(2,2-difluoroethyl)-3-({(1S,4S)-5-[6-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-(2,2-difluoroethyl)-3-({(1S,4S)-5-[4-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-(2,2-difluoroethyl)-3-({(1S,4S)-5-[2-(trifluoromethyl)pyridin-4-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-(2,2-difluoroethyl)-3-({(1S,4S)-5-[4-(trifluoromethyl)pyrimidin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-(2,2-difluoroethyl)-3-({(1S,4S)-5-[6-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-(2,2-difluoroethyl)-3-({(1S,4S)-5-[6-(trifluoromethyl)pyrazin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-(2,2-difluoroethyl)-3-({(1S,4S)-5-[2-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-(2,2-difluoroethyl)-3-({(1S,4S)-5-[5-(trifluoromethyl)pyridazin-3-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-4-O-methyl-3-{[(1R,3S)-3-(2,2,2-trifluoroethyl)-3-({(1S,4S)-5-[6-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-4-O-methyl-3-{[(1R,3S)-3-(2,2,2-trifluoroethyl)-3-({(1S,4S)-5-[4-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-4-O-methyl-3-{[(1R,3S)-3-(2,2,2-trifluoroethyl)-3-({(1S,4S)-5-[2-(trifluoromethyl)pyridin-4-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-4-O-methyl-3-{[(1R,3S)-3-(2,2,2-trifluoroethyl)-3-({(1S,4S)-5-[4-(trifluoromethyl)pyrimidin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-4-O-methyl-3-{[(1R,3S)-3-(2,2,2-trifluoroethyl)-3-({(1S,4S)-5-[6-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-4-O-methyl-3-{[(1R,3S)-3-(2,2,2-trifluoroethyl)-3-({(1S,4S)-5-[6-(trifluoromethyl)pyrazin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-4-O-methyl-3-{[(1R,3S)-3-(2,2,2-trifluoroethyl)-3-({(1S,4S)-5-[2-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-4-O-methyl-3-{[(1R,3S)-3-(2,2,2-trifluoroethyl)-3-({(1S,4S)-5-[5-(trifluoromethyl)pyridazin-3-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1S,4S)-4-isopropyll-4-({(1S,4S)-5-[4-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopent-2-en-1-yl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1S,4S)-4-isopropyll-4-({(1S,4S)-5-[4-(trifluoromethyl)pyrimidin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopent-2-en-1-yl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1S,4S)-4-isopropyll-4-({(1S,4S)-5-[6-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopent-2-en-1-yl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1S,4S)-4-isopropyll-4-({(1S,4S)-5-[6-(trifluoromethyl)pyrazin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopent-2-en-1-yl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-3-{[(1R,3S)-3-{[(1S,4S)-5-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]carbonyl}-3-ethylcyclopentyl]amino}-2,3-dideoxy-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-3-{[(1R,3S)-3-{[(1S,4S)-5-(tert-butoxycarbonyl)-2,5-diazabicyclo[2.2.1]hept-2-yl]carbonyl}-3-(2,2,2-trifluoroethyl)cyclopentyl]amino}-2,3-dideoxy-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-(1-hydroxycyclobutyl)-3-({(1S,4S)-5-[6-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-(1-hydroxycyclobutyl)-3-({(1S,4S)-5-[4-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-(1-hydroxycyclobutyl)-3-({(1S,4S)-5-[4-(trifluoromethyl)pyrimidin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-(1-hydroxycyclobutyl)-3-({(1S,4S)-5-[2-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-(1-hydroxycyclobutyl)-3-({(1S,4S)-5-[6-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-(1-hydroxycyclobutyl)-3-({(1S,4S)-5-[6-(trifluoromethyl)pyrazin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[(1R,3S)-3-(1-hydroxycyclobutyl)-3-({(1S,4S)-5-[2-(trifluoromethyl)pyridin-4-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methyl-D-erythro-pentitol;
1,5-anhydro-2,3-dideoxy-3-{[3-(1-hydroxy-1-methylethyl)-3-({5-[4-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methylpentitol;
1,5-anhydro-2,3-dideoxy-3-{[3-(1-hydroxy-1-methylethyl)-3-({5-[6-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methylpentitol;
1,5-anhydro-2,3-dideoxy-3-{[3-(1-hydroxy-1-methylethyl)-3-({5-[4-(trifluoromethyl)pyrimidin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methylpentitol;
1,5-anhydro-2,3-dideoxy-3-{[3-(1-hydroxy-1-methylethyl)-3-({5-[5-(trifluoromethyl)pyridazin-3-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methylpentitol;
1,5-anhydro-2,3-dideoxy-3-{[3-(1-hydroxy-1-methylethyl)-3-({5-[2-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methylpentitol;
1,5-Anhydro-2,3-dideoxy-3-{[3-(1-hydroxy-1-methylethyl)-3-({5-[6-(trifluoromethyl)pyridin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methylpentitol;
1,5-anhydro-2,3-dideoxy-3-{[3-(1-hydroxy-1-methylethyl)-3-({5-[2-(trifluoromethyl)pyridin-4-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methylpentitol;
and
1,5-anhydro-2,3-dideoxy-3-{[3-(1-hydroxy-1-methylethyl)-3-({5-[6-(trifluoromethyl)pyrazin-2-yl]-2,5-diazabicyclo[2.2.1]hept-2-yl}carbonyl)cyclopentyl]amino}-4-O-methylpentitol.

57 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/616,375Filed 14 Sep 2012 · continuation
Priority: 26 Nov 2008
Published: US 2013/0197008 A11 Aug 2013
Granted: 3 Feb 2015
Term ends: Not estimatedThe source records don’t support an estimate.

Classification36 codes

C07D 487/08
In which the condensed system contains two hetero rings: bridged systems
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…
A61P 3/02
Drugs for disorders of the metabolism: nutrients, e.g. vitamins, minerals

Family

Application61/118,053Us provisional application · filed 26 Nov 2008
PCT/IB2009/055232Parent of this continuation · filed 20 Nov 2009
Application12/795,266Parent of this continuation · filed 7 Jun 2010
US 2013/0197008 A1Pre-grant publication · published 1 Aug 2013
US 8,293,903 B2Parent of this continuation
US 2011/0144129 A1Published application
US 8,946,413 B2This patent

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

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Abstract

There is provided a compound of Formula I(a) or I(b): or a pharmaceutically acceptable salt thereof, wherein the various substitutents are defined herein.

A compound of Formula I(a) or I(b):

or a pharmaceutically acceptable salt thereof, wherein:
A is O or CF2;
W is CR13R14, C(O), CHOR15, CHF, or CF2;
R1 is H or (C1-C6)alkyl optionally substituted by 1-3 substituents selected from halo, OH, CO2H, CO2—(C1-C6)alkyl, or (C1-C3) alkoxy;
R2 and R3 are each, independently, H, (C1-C6)alkyl, (C1-C6) haloalkyl, halo, (C3-C6) cycloalkyl, CN, OH, OCOR12;
wherein said (C1-C6)alkyl is optionally substituted with one or more substituents selected from F, (C1-C3) alkoxy, OH, CN or CO2R12;
R8 and R9 are each, independently, H, (C1-C6)alkyl, (C1-C6)haloalkyl, (C3-C6)cycloalkyl, CN, OH, OCOR12;
wherein said (C1-C6)alkyl is optionally substituted with one or more substituents selected from F, (C1-C3) alkoxy, OH, CN or CO2R12;
R2 and R9, taken together may form a 5-8 membered ring;
R4 and R7, taken together may form a 5-8 membered ring;
R4 and R5 are each, independently, H, CN, (C1-C6)alkyl, halo, (C1-C3)alkoxy, (C1-C3)haloalkoxy, (C3-C6)cycloalkyl, OH, CO2R12, OCOR12, wherein said (C1-C6)alkyl is optionally substituted with one or more substituents selected from F, (C1-C3) alkoxy, OH or CO2R12;
R6 and R7 are each, independently, H, CN, (C1-C6)alkyl, halo, (C1-C3)alkoxy, (C1-C3)haloalkoxy, (C3-C6)cycloalkyl, OH, CO2R12, OCOR12, wherein said (C1-C6)alkyl is optionally substituted with one or more substituents selected from F, (C1-C3) alkoxy, OH or CO2R12;
or R2 and R3 together with the carbon atom to which they are attached form a 3-7 membered spirocyclyl group;
or R4 and R5 together with the carbon atom to which they are attached form a 3-7 membered spirocyclyl group;
or R3 and R4 together with the C atoms to which they are attached form a fused 3-7 membered cycloalkyl group or 3-7 membered heterocycloalkyl group;
R10 is (C1-C6)alkyl, (C1-C6)haloalkyl, (C1-C6)hydroxyalkyl, (C1-C6)alkoxy, (C3-C6)cycloalkyl, hydroxy(C3-C6)cycloalkyl, alkoxy cycloalkyl, OH, (C1-C5)heterocyclyl, amino, aryl or CN,
R11 is aryl or heteroaryl, said R11 optionally, independently substituted by one or more (C1-C6) alkyl, halo, (C1-C6)haloalky(C1-C3)alkoxy, OH, amino, C(O)NH2, NH2SO2, SF5, or CN;
R12 is H, (C1-C4)alkyl, or (C3-C6)cycloalkyl;
R13 is H, halo, (C1-C4)alkyl, (C1-C4)alkoxy, or OH;
R14 is H, halo, (C1-C4)alkyl, (C1-C4)alkoxy or OH;
and
R15 is H, (C1-C6)alkyl or (C3-C6)cycloalkyl.

19 more elements

Facts

Application

13/616,375Filed 14 Sep 2012 · continuation

Priority

26 Nov 2008

Published

US 2013/0197008 A11 Aug 2013

Granted

3 Feb 2015

Term ends

Not estimatedThe source records don’t support an estimate.

Classification36 codes

C07D 487/08
In which the condensed system contains two hetero rings: bridged systems
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…
A61P 1/16
Drugs for disorders of the alimentary tract or the digestive system: for liver or gallbladder disorders, e.g. hepatoprotective agents,…
A61P 3/02
Drugs for disorders of the metabolism: nutrients, e.g. vitamins, minerals

Family

Application61/118,053Us provisional application · filed 26 Nov 2008

PCT/IB2009/055232Parent of this continuation · filed 20 Nov 2009

Application12/795,266Parent of this continuation · filed 7 Jun 2010

US 2013/0197008 A1Pre-grant publication · published 1 Aug 2013

US 8,293,903 B2Parent of this continuation

US 2011/0144129 A1Published application

US 8,946,413 B2This patent

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