US 10,100,043 B2Granted

Substituted aldehyde compounds and methods for their use in increasing tissue oxygenation

AssigneesGlobal Blood Therapeutics, Inc., Cytokinetics, Inc.

InventorsBrian Metcalf, Chihyuan Chuang, Zhe Li

Life of this patent

Estimating the term…

Abstract

Provided are cycloalkyl- and cycloalkenyl-substituted benzaldehydes and heteroaldehydes of formula (I) that act as allosteric modulators of hemoglobin, methods and intermediates for their preparation, pharmaceutical compositions containing the modulators, and methods for their use in treating disorders mediated by hemoglobin and disorders that would benefit from increased tissue oxygenation.

Claims26

Dependent claims

A compound of Formula (I):

a tautomer, a stereoisomer, a mixture of stereoisomers, or a pharmaceutically acceptable salt thereof, wherein:
Q is cycloalkyl or cycloalkenyl, each of which is substituted with one to three Ra;
Y is CR1aR1b, wherein
R1a is H or halo, and
R1b is H or halo;
X is 0;
T1, T2, T3, and T4 are independently C or N provided that at least one of T1, T2, T3, and T4 is C;
wherein when T1, T2, T3, or T4 are N, then R2, R3, R4, or R5, respectively, are absent;
R2, R3, and R4 are independently hydrogen, halo, Rb, ORd, or NRdNRd;
R5 is selected from the group consisting of hydrogen, halo, Rb, ORd, —O(CH2)zORd, —O(CH2)zNRdRd, OC(O)Re, SRd, CN, NO2, CO2Rd, CONRdRd, C(O)Rd, OC(O)NRdRd, NRdRd, NRdC(O)Re, NRdC(O)2Re, NRdC(O)NRdRd, S(O)Re, S(O)2Re, NRdS(O)2Re, S(O)2NRdRd, and N3;
wherein z is 0, 1, 2, 3, 4, 5, or 6;
or
R5 is —(CH2)pR5a, wherein p is 0 or 1 and R5a is OH;
R6 and R7 together form oxo or an aldehyde protecting group, or
R6 together with R1b or R5 forms a cyclic ether, wherein
one of R1b or R5a is O, R6 is a bond, and
R7 is selected from the group consisting of OH, C1-8alkoxy, and haloC1-8alkoxy;
each Ra is independently selected from the group consisting of halo, Rb, ORd, —(CH2)kCO2(C1-8alkyl)OH, —(CH2)kCO2Rd, —(CH2)kCONRdRd, —(CH2)kC(O)Rd, —(CH2)karyl optionally substituted with one to three Rc, —(CH2)kheteroaryl optionally substituted with one to three Rc, and —(CH2)kheterocycloalkyl optionally substituted with one to three Rc ;
wherein k is 0, 1, 2, 3, 4, 5, or 6;
and wherein at least one of Ra is selected from the group consisting of ORd, —(CH2)kCO2(C1-8alkyl)OH, —(CH2)kCO2Rd, —(CH2)kCONRdRd, —(CH2)kC(O)Rd, —(CH2)karyl optionally substituted with one to three Rc, —(CH2)kheteroaryl optionally substituted with one to three Rc, —(CH2)kheterocycloalkyl optionally substituted with one to three Rc, substituted C1-8alkyl, substituted C2-8alkenyl, and substituted C2-8 alkynyl;
wherein the substituted C1-8alkyl, substituted C2-8alkenyl, and substituted C2-8 alkynyl are each substituted with one to three halo, ORd, or NRdRd;
each Rb is independently selected from the group consisting of C1-8alkyl, C2-8alkenyl, and C2-8 alkynyl, each optionally independently substituted with one to three halo, ORd, or NRdRd;
each Rc is independently selected from the group consisting of halo, C1-8alkyl, haloC1-8alkyl, C2-8alkenyl, haloC2-8 alkenyl, C2-8alkynyl, haloC2-8alkynyl, (CH2)mORf, heteroaryl, cycloalkyl, and heterocycloalkyl;
wherein m is selected from the group consisting of 0, 1, 2, 3, 4, 5, and 6;
each Rd is independently selected from the group consisting of hydrogen, C1-8 alkyl, haloC1-8alkyl, C2-8 alkenyl, haloC2-8alkenyl, C2-8 alkynyl, haloC2-8alkynyl, —(CH2)kheterocycloalkyl, and —(CH2)uO—(CH2)uH;
wherein k is 0, 1, 2, 3, 4, 5, or 6 and each u is independently 1, 2, 3, 4, 5, or 6;
each Rf is independently selected from the group consisting of hydrogen, C1-8 alkyl, haloC1-8alkyl, C2-8 alkenyl, haloC2-8alkenyl, C2-8 alkynyl, and haloC2-8alkynyl;
and
Re is C1-8alkyl, haloC1-8alkyl, C2-8 alkenyl, haloC2-8alkenyl, C2-8alkynyl, or haloC2-8alkynyl;
provided that:
at least one of R4 and R5 is other than hydrogen or
T1 and T3 are C;
T2 is N and T4 is C, or T2 is C and T4 is N.

30 more elements

A compound selected from the group consisting of

cis-methyl4-((2-formyl-3-hydroxyphenoxy)methyl)cyclohexanecarboxylate;
cis-4((2-formyl-3-hydroxyphenoxy)methyl)cyclohexanecarboxylic acid;
(1R,3S)-3-((2-formyl-3-hydroxyphenoxy)methyl)cyclohexanecarboxylic acid;
trans-methyl4-((2-formyl-3-hydroxyphenoxy)methyl)cyclohexanecarboxylate;
trans-4-((2-formyl-3-hydroxyphenoxy)methyl)cyclohexanecarboxylic acid;
methyl3-((2-formyl-3-hydroxyphenoxy)methyl)cyclohexanecarboxylate;
trans-methyl4-((2-formyl-3-methoxyphenoxy)methyl)cyclohexanecarboxylate;
2-hydroxy-6-((3,4,5,6-tetrahydro-[1,1’-biphenyl]-2-yl)methoxy)benzaldehyde;
2-hydroxy-6-((2-phenylcyclohexyl)methoxy)benzaldehyde;
2-hydroxy-6-((2-(1-isopropyl-1H-pyrazol-5-yl)cyclohex-1-en-1-yl)methoxy)benzaldehyde;
2-hydroxy-6-[[2-(2-hydroxypropan-2-yl)cyclohexyl]methoxy]benzaldehyde;
2-hydroxy-6-[[2-(2-hydroxybutan-2-yl)cyclohexyl]methoxy]benzaldehyde;
2-hydroxy-6-[[2-(2-hydroxypentan-2-yl)cyclohexyl]methoxy]benzaldehyde;
2-hydroxy-6-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexyl]methoxy]benzaldehyde;
2-[[2-(2-chlorophenyl)cyclohexyl]methoxy]-6-hydroxybenzaldehyde;
2-hydroxy--[[2-(3-propan-2-ylimidazol-4-yl)cyclohexyl]methoxy]benzaldehyde;
2-hydroxy-6-[(2-phenylcyclohexyl)methoxy]benzaldehyde;
2-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]-6-hydroxybenzaldehyde;
2-[[2-(2-fluorophenyl)cyclohexyl]methoxy]-6-hydroxybenzaldehyde;
2-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexyl]methoxy]-6-hydroxybenzaldehyde;
2-hydroxy-6-[[2-(2-methoxypyridin-3-yl)cyclohexyl]methoxy]benzaldehyde;
2-hydroxy-6-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexyl]methoxy]benzaldehyde;
2-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexyl]methoxy]-6-hydroxybenzaldehyde;
2-hydroxy-6-[[2-(2-propylpyrazol-3-yl)cyclohexyl]methoxy]benzaldehyde;
2-[[2-(2-chloropyridin-3-yl)cyclohexyl]methoxy]-6-hydroxybenzaldehyde;
2-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexyl]methoxy]-6-hydroxybenzaldehyde;
2-hydroxy-6-[[2-(2-methoxyphenyl)cyclohexyl]methoxy]benzaldehyde;
2-hydroxy-6-[[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]benzaldehyde;
2-hydroxy-6-[[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexyl]methoxy]benzaldehyde;
2-[[2-(2-ethylpyrazol-3-yl)cyclohexyl]methoxy]-6-hydroxybenzaldehyde;
2-hydroxy-6-[[2-(2-hydroxypentan-2-yl)cyclohexyl]methoxy]-3-methylbenzaldehyde;
2-hydroxy-6-[[2-(2-hydroxybutan-2-yl)cyclohexyl]methoxy]-3-methylbenzaldehyde;
2-hydroxy-6-[[2-(2-hydroxypropan-2-yl)cyclohexyl]methoxy]-3-methylbenzaldehyde;
6-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexyl]methoxy]-2-hydroxy-3-methylbenzaldehyde;
2-hydroxy-3-methyl-64[2-(2-propan-2-ylpyrazol-3-yl)cyclohexyl]methoxy]benzaldehyde;
6-[[2-(2-chloropyridin-3-yl)cyclohexyl]methoxy]-2-hydroxy-3-methylbenzaldehyde;
6-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]-2-hydroxy-3-methylbenzaldehyde;
6-[[2-(2-fluorophenyl)cyclohexyl]methoxy]-2-hydroxy-3-methylbenzaldehyde;
6-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexyl]methoxy]-2-hydroxy-3-methylbenzaldehyde;
2-hydroxy-6-[[2-(2-methoxyphenyl)cyclohexyl]methoxy]-3-methylbenzaldehyde;
2-hydroxy-3-methyl-6-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexyl]methoxy]benzaldehyde;
2-hydroxy-3-methyl-6-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexyl]methoxy]benzaldehyde;
6-[[2-(2-chlorophenyl)cyclohexyl]methoxy]-2-hydroxy-3-methylbenzaldehyde;
2-hydroxy-3-methyl-6-[[2-(2-propylpyrazol-3-yl)cyclohexyl]methoxy]benzaldehyde;
2-hydroxy-3-methyl-6-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexyl]methoxy]benzaldehyde;
2-hydroxy-3-methyl-6-[(2-phenylcyclohexyl)methoxy]benzaldehyde;
2-hydroxy-3-methyl-6-[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]benzaldehyde;
2-hydroxy-6-[[2-(2-methoxypyridin-3-yl)cyclohexyl]methoxy]-3-methylbenzaldehyde;
6-[[2-(2-ethylpyrazol-3-yl)cyclohexyl]methoxy]-2-hydroxy-3-methylbenzaldehyde;
6-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexyl]methoxy]-2-hydroxy-3-methylbenzaldehyde;
3-chloro-2-hydroxy-6-[[2-(2-hydroxybutan-2-yl)cyclohexyl]methoxy]benzaldehyde;
3-chloro-2-hydroxy-6-[[2-(2-hydroxypropan-2-yl)cyclohexyl]methoxy]benzaldehyde;
3-chloro-2-hydroxy-6-[[2-(2-hydroxypentan-2-yl)cyclohexyl]methoxy]benzaldehyde;
3-chloro-6-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]-2-hydroxybenzaldehyde;
3-chloro-2-hydroxy-6-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexyl]methoxy]benzaldehyde;
3-chloro-2-hydroxy-6-[[2-(2-propylpyrazol-3-yl)cyclohexyl]methoxy]benzaldehyde;
3-chloro-6-[[2-(2-chloropyridin-3-yl)cyclohexyl]methoxy]-2-hydroxybenzaldehyde;
3-chloro-2-hydroxy-6-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexyl]methoxy]benzaldehyde;
3-chloro-2-hydroxy-6-[(2-phenylcyclohexyl)methoxy]benzaldehyde;
3-chloro-2-hydroxy-6-[[2-(2-methoxyphenyl)cyclohexyl]methoxy]benzaldehyde;
3-chloro-2-hydroxy-6-[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]benzaldehyde;
3-chloro-6-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexyl]methoxy]-2-hydroxybenzaldehyde;
3-chloro-6-[[2-(2-ethylpyrazol-3-yl)cyclohexyl]methoxy]-2-hydroxybenzaldehyde;
3-chloro-6-[[2-(2-chlorophenyl)cyclohexyl]methoxy]-2-hydroxybenzaldehyde;
3-chloro-2-hydroxy-6-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexyl]methoxy]benzaldehyde;
3-chloro-6-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexyl]methoxy]-2-hydroxybenzaldehyde;
3-chloro-6-[[2-(2-fluorophenyl)cyclohexyl]methoxy]-2-hydroxybenzaldehyde;
3-chloro-6-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexyl]methoxy]-2-hydroxybenzaldehyde;
3-chloro-2-hydroxy-6-[[2-(2-methoxypyridin-3-yl)cyclohexyl]methoxy]benzaldehyde;
3-chloro-2-hydroxy-6-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexyl]methoxy]benzaldehyde;
2-fluoro-6-[[2-(2-hydroxypropan-2-yl)cyclohexyl]methoxy]benzaldehyde;
2-fluoro-6-[[2-(2-hydroxypentan-2-yl)cyclohexyl]methoxy]benzaldehyde;
2-fluoro-6-[[2-(2-hydroxybutan-2-yl)cyclohexyl]methoxy]benzaldehyde;
2-fluoro-6-[[2-(2-propylpyrazol-3-yl)cyclohexyl]methoxy]benzaldehyde;
2-[[2-(2-chloropyridin-3-yl)cyclohexyl]methoxy]-6-fluorobenzaldehyde;
2-fluoro-6-[[2-(2-methoxyphenyl)cyclohexyl]methoxy]benzaldehyde;
2-fluoro-6[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]benzaldehyde;
2-fluoro-6[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexyl]methoxyThenzaldehyde;
2-[[2-(2-ethylpyrazol-3-yl)cyclohexyl]methoxy]-6-fluorobenzaldehyde;
2-[[2-(2-chlorophenyl)cyclohexyl]methoxy]-6-fluorobenzaldehyde;
2-fluoro-6-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexyl]methoxy]benzaldehyde;
2-fluoro-6-[(2-phenylcyclohexyl)methoxy]benzaldehyde;
2-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]-6-fluorobenzaldehyde;
2-fluoro-6-[[2-(2-fluorophenyl)cyclohexyl]methoxy]benzaldehyde;
2-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexyl]methoxy]-6-fluorobenzaldehyde;
2-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexyl]methoxy]-6-fluorobenzaldehyde;
2-fluoro-6-[[2-(2-methoxypyridin-3-yl)cyclohexyl]methoxy]benzaldehyde;
2-fluoro-6-[[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexyl]methoxy]benzaldehyde;
2-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexyl]methoxy]-6-fluorobenzaldehyde;
2-fluoro-6-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexyl]methoxy]benzaldehyde;
2-hydroxy-6-[[2-(2-hydroxypropan-2-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
2-hydroxy-6-[[2-(2-hydroxybutan-2-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
2-hydroxy-6-[[2-(2-hydroxypentan-2-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
2-hydroxy-6-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]benzaldehyde;
2-[[2-(2-chlorophenyl)cyclohexen-1-yl]methoxy]-6-hydroxybenzaldehyde;
2-hydroxy-6-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
2-[[2-(2-fluorophenyl)cyclohexen-1-yl]methoxy]-6-hydroxybenzaldehyde;
2-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-6-hydroxybenzaldehyde;
2-hydroxy-6-[[2-(2-methoxypyridin-3-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
2-hydroxy-6-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
2-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-6-hydroxybenzaldehyde;
2-hydroxy-6-[[2-(2-propylpyrazol-3-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
2-[[2-(2-chloropyridin-3-yl)cyclohexen-1-yl]methoxy]-6-hydroxybenzaldehyde;
2-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-6-hydroxybenzaldehyde;
2-hydroxy-6-[[2-(2-methoxyphenyl)cyclohexen-1-yl]methoxy]benzaldehyde;
2-hydroxy-6-[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]benzaldehyde;
2-hydroxy-6-[[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]benzaldehyde;
2-[[2-(2-ethylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-6-hydroxybenzaldehyde;
2-hydroxy-6-[[2-(2-hydroxypentan-2-yl)cyclohexen-1-yl]methoxy]-3-methylbenzaldehyde;
2-hydroxy-6-[[2-(2-hydroxybutan-2-yl)cyclohexen-1-yl]methoxy]-3-methylbenzaldehyde;
2-hydroxy-6-[[2-(2-hydroxypropan-2-yl)cyclohexen-1-yl]methoxy]-3-methylbenzaldehyde;
6-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-hydroxy-3-methylbenzaldehyde;
2-hydroxy-3-methyl-6-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
6-[[2-(2-chloropyridin-3-yl)cyclohexen-1-yl]methoxy]-2-hydroxy-3-methylbenzaldehyde;
6-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]-2-hydroxy-3-methylbenzaldehyde;
6-[[2-(2-fluorophenyl)cyclohexen-1-yl]methoxy]-2-hydroxy-3-methylbenzaldehyde;
6-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-hydroxy-3-methylbenzaldehyde;
2-hydroxy-6-[[2-(2-methoxyphenyl)cyclohexen-1-yl]methoxy]-3-methylbenzaldehyde;
2-hydroxy-3-methyl-6-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]benzaldehyde;
2-hydroxy-3-methyl-6-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]benzaldehyde;
6-[[2-(2-chlorophenyl)cyclohexen-1-yl]methoxy]-2-hydroxy-3-methylbenzaldehyde;
2-hydroxy-3-methyl-6-[[2-(2-propylpyrazol-3-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
2-hydroxy-3-methyl-6-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
2-hydroxy-3-methyl-6-[(2-phenylcyclohexen-1-yl)methoxy]benzaldehyde;
2-hydroxy-3-methyl-6-[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]benzaldehyde;
2-hydroxy-6-[[2-(2-methoxypyridin-3-yl)cyclohexen-1-yl]methoxy]-3-methylbenzaldehyde;
6-[[2-(2-ethylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-hydroxy-3-methylbenzaldehyde;
6-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-hydroxy-3-methylbenzaldehyde;
3-chloro-2-hydroxy-6-[[2-(2-hydroxybutan-2-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
3-chloro-2-hydroxy-6-[[2-(2-hydroxypropan-2-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
3-chloro-2-hydroxy-6-[[2-(2-hydroxypentan-2-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
3-chloro-6-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]-2-hydroxybenzaldehyde;
3-chloro-2-hydroxy-6-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]benzaldehyde;
3-chloro-2-hydroxy-6-[[2-(2-propylpyrazol-3-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
3-chloro-6-[[2-(2-chloropyridin-3-yl)cyclohexen-1-yl]methoxy]-2-hydroxybenzaldehyde;
3-chloro-2-hydroxy-6-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
3-chloro-2-hydroxy-6-[(2-phenylcyclohexen-1-yl)methoxy]benzaldehyde;
3-chloro-2-hydroxy-6-[[2-(2-methoxyphenyl)cyclohexen-1-yl]methoxy]benzaldehyde;
3-chloro-2-hydroxy-6-[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]benzaldehyde;
3-chloro-6-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-hydroxybenzaldehyde;
3-chloro-6-[[2-(2-ethylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-hydroxybenzaldehyde;
3-chloro-6-[[2-(2-chlorophenyl)cyclohexen-1-yl]methoxy]-2-hydroxybenzaldehyde;
3-chloro-2-hydroxy-6-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
3-chloro-6-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-hydroxybenzaldehyde;
3-chloro-6-[[2-(2-fluorophenyl)cyclohexen-1-yl]methoxy]-2-hydroxybenzaldehyde;
3-chloro-6-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-hydroxybenzaldehyde;
3-chloro-2-hydroxy-6-[[2-(2-methoxypyridin-3-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
3-chloro-2-hydroxy-6-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]benzaldehyde;
2-fluoro-6-[[2-(2-hydroxypropan-2-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
2-fluoro-6-[[2-(2-hydroxypentan-2-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
2-fluoro-6-[[2-(2-hydroxybutan-2-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
2-fluoro-6-[[2-(2-propylpyrazol-3-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
2-[[2-(2-chloropyridin-3-yl)cyclohexen-1-yl]methoxy]-6-fluorobenzaldehyde;
2-fluoro-6-[[2-(2-methoxyphenyl)cyclohexen-1-yl]methoxy]benzaldehyde;
2-fluoro-6-[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]benzaldehyde;
2-fluoro-6-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]benzaldehyde;
2-[[2-(2-ethylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-6-fluorobenzaldehyde;
2-[[2-(2-chlorophenyl)cyclohexen-1-yl]methoxy]-6-fluorobenzaldehyde;
2-fluoro-6-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
2-fluoro-6-[(2-phenylcyclohexen-1-yl)methoxy]benzaldehyde;
2-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]-6-fluorobenzaldehyde;
2-fluoro-6-[[2-(2-fluorophenyl)cyclohexen-1-yl]methoxy]benzaldehyde;
2-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-6-fluorobenzaldehyde;
2-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-6-fluorobenzaldehyde;
2-fluoro-6-[[2-(2-methoxypyridin-3-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
2-fluoro-6-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]benzaldehyde;
2-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-6-fluorobenzaldehyde;
2-fluoro-6-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexen-1-yl]methoxy]benzaldehyde;
3-[[2-(2-hydroxypentan-2-yl)cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-hydroxybutan-2-yl)cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-hydroxypropan-2-yl)cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-propylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-chloropyridin-3-yl)cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-methoxyphenyl)cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-ethylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-chlorophenyl)cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[(2-phenylcyclohexyl)methoxy]pyridine-2-carbaldehyde;
3-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-fluorophenyl)cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-methoxypyridin-3-yl)cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-hydroxybutan-2-yl)cyclohexyl]methoxy]-6-methylpyridine-2-carbaldehyde;
3-[[2-(2-hydroxypropan-2-yl)cyclohexyl]methoxy]-6-methylpyridine-2-carbaldehyde;
3-[[2-(2-hydroxypentan-2-yl)cyclohexyl]methoxy]-6-methylpyridine-2-carbaldehyde;
3-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexyl]methoxy]-6-methylpyridine-2-carbaldehyde;
3-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexyl]methoxy]-6-methylpyridine-2-carbaldehyde;
6-methyl-3-[[2-(2-propylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-chloropyridin-3-yl)cyclohexyl]methoxy]-6-methylpyridine-2-carbaldehyde;
6-methyl-3-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-methoxyphenyl)cyclohexyl]methoxy]-6-methylpyridine-2-carbaldehyde;
6-methyl-3-[[242-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-2-carbaldehyde;
6-methyl-3-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-ethylpyrazol-3-yl)cyclohexyl]methoxy]-6-methylpyridine-2-carbaldehyde;
3-[[2-(2-chlorophenyl)cyclohexyl]methoxy]-6-methylpyridine-2-carbaldehyde;
6-methyl-3-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-2-carbaldehyde;
6-methyl-3-[(2-phenylcyclohexyl)methoxy]pyridine-2-carbaldehyde;
3-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]-6-methylpyridine-2-carbaldehyde;
3-[[2-(2-fluorophenyl)cyclohexyl]methoxy]-6-methylpyridine-2-carbaldehyde;
3-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexyl]methoxy]-6-methylpyridine-2-carbaldehyde;
3-[[2-(2-methoxypyridin-3-yl)cyclohexyl]methoxy]-6-methylpyridine-2-carbaldehyde;
6-methyl-3-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-2-carbaldehyde;
3-chloro-5-[[2-(2-hydroxypropan-2-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-hydroxypentan-2-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-hydroxybutan-2-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-methoxyphenyl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-ethylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-chlorophenyl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-fluorophenyl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-methoxypyridin-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-propylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-chloropyridin-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[(2-phenylcyclohexyl)methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-hydroxypentan-2-yl)cyclohexyl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-[[2-(2-hydroxybutan-2-yl)cyclohexyl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-[[2-(2-hydroxypropan-2-yl)cyclohexyl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-[[2-(2-methoxyphenyl)cyclohexyl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-methyl-5-[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-methyl-5-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-ethylpyrazol-3-yl)cyclohexyl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-methyl-5-[(2-phenylcyclohexyl)methoxy]pyridine-4-carbaldehyde;
3-[[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-[[2-(2-fluorophenyl)cyclohexyl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexyl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexyl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-[[2-(2-methoxypyridin-3-yl)cyclohexyl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-methyl-5-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexyl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-methyl-5-[[2-(2-propylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-chloropyridin-3-yl)cyclohexyl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-methyl-5-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-chlorophenyl)cyclohexyl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-methyl-5-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-hydroxy-5-[[2-(2-hydroxypentan-2-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-hydroxy-5-[[2-(2-hydroxybutan-2-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-hydroxy-5-[[2-(2-hydroxypropan-2-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-hydroxy-5-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]-5-hydroxypyridine-4-carbaldehyde;
3-[[2-(2-fluorophenyl)cyclohexyl]methoxy]- 5-hydroxypyridine-4-carbaldehyde;
3-hydroxy-5-[[2-(2-methoxypyridin-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-hydroxy-5-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexyl]methoxy]-5-hydroxypyridine-4-carbaldehyde;
3-hydroxy-5-[[2-(2-propylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-chloropyridin-3-yl)cyclohexyl]methoxy]-5-hydroxypyridine-4-carbaldehyde;
3-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexyl]methoxy]-5-hydroxypyridine-4-carbaldehyde;
3-hydroxy-5-[[2-(2-methoxyphenyl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-hydroxy-5-[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-hydroxy-5-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-hydroxy-5-[[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-ethylpyrazol-3-yl)cyclohexyl]methoxy]-5-hydroxypyridine-4-carbaldehyde;
3-[[2-(2-chlorophenyl)cyclohexyl]methoxy]-5-hydroxypyridine-4-carbaldehyde;
3-hydroxy-5-[(2-phenylcyclohexyl)methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexyl]methoxy]-5-hydroxypyridine-4-carbaldehyde;
3-[[2-(2-hydroxybutan-2-yl)cyclohexyl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-[[2-(2-hydroxypropan-2-yl)cyclohexyl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-[[2-(2-hydroxypentan-2-yl)cyclohexyl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-[[2-(2-fluorophenyl)cyclohexyl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexyl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-methoxy-5-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-methoxy-5-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-chlorophenyl)cyclohexyl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-methoxy-5-[[2-(2-propylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-methoxy-5-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-methoxy-5-[(2-phenylcyclohexyl)methoxy]pyridine-4-carbaldehyde;
3-methoxy-5-[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexyl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-methoxy-5-[[2-(2-methoxypyridin-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-ethylpyrazol-3-yl)cyclohexyl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-methoxy-5-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexyl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-[[2-(2-chloropyridin-3-yl)cyclohexyl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-[[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-methoxy-5-[[2-(2-methoxyphenyl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-hydroxy-5-[[2-(2-hydroxybutan-2-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-hydroxy-5-[[2-(2-hydroxypropan-2-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-hydroxy-5-[[2-(2-hydroxypentan-2-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-ethylpyrazol-3-yl)cyclohexyl]methoxy]-2-hydroxypyridine-4-carbaldehyde;
5-[[2-(2-chlorophenyl)cyclohexyl]methoxy]-2-hydroxypyridine-4-carbaldehyde;
2-hydroxy-5-[(2-phenylcyclohexyl)methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexyl]methoxy]-2-hydroxypyridine-4-carbaldehyde;
5-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexyl]methoxy]-2-hydroxypyridine-4-carbaldehyde;
2-hydroxy-5-[[2-(2-methoxypyridin-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-hydroxy-5-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexyl]methoxy]-2-hydroxypyridine-4-carbaldehyde;
2-hydroxy-5-[[2-(2-propylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-chloropyridin-3-yl)cyclohexyl]methoxy]-2-hydroxypyridine-4-carbaldehyde;
2-hydroxy-5-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-hydroxy-5-[[2-(2-methoxyphenyl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-hydroxy-5-[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-hydroxy-5-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-hydroxy-5-[[2-[2-(2-propan-2-ylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
5-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]-2-hydroxypyridine-4-carbaldehyde;
5-[[2-(2-fluorophenyl)cyclohexyl]methoxy]-2-hydroxypyridine-4-carbaldehyde;
5-[[2-(2-hydroxypropan-2-yl)cyclohexyl]methoxy]-2-methoxypyridine-4-carbaldehyde;
5-[[2-(2-hydroxypentan-2-yl)cyclohexyl]methoxy]-2-methoxypyridine-4-carbaldehyde;
5-[[2-(2-hydroxybutan-2-yl)cyclohexyl]methoxy]-2-methoxypyridine-4-carbaldehyde;
2-methoxy-5-[[2-(2-methoxypyridin-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexyl]methoxy]-2-methoxypyridine-4-carbaldehyde;
2-methoxy-5-[[2-(2-propylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-chloropyridin-3-yl)cyclohexyl]methoxy]-2-methoxypyridine-4-carbaldehyde;
5-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexyl]methoxy]-2-methoxypyridine-4-carbaldehyde;
2-methoxy-5-[[2-(2-methoxyphenyl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-methoxy-5-[[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-methoxy-5-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-methoxy-5-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-ethylpyrazol-3-yl)cyclohexyl]methoxy]-2-methoxypyridine-4-carbaldehyde;
5-[[2-(2-chlorophenyl)cyclohexyl]methoxy]-2-methoxypyridine-4-carbaldehyde;
2-methoxy-5-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-methoxy-5-[(2-phenylcyclohexyl)methoxy]pyridine-4-carbaldehyde;
5-[[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]-2-methoxypyridine-4-carbaldehyde;
5-[[2-(2-fluorophenyl)cyclohexyl]methoxy]-2-methoxypyridine-4-carbaldehyde;
5-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexyl]methoxy]-2-methoxypyridine-4-carbaldehyde;
2-methoxy-5-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-hydroxypropan-2-yl)cyclohexyl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-hydroxypentan-2-yl)cyclohexyl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-hydroxybutan-2-yl)cyclohexyl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
2-(2-methoxyethoxy)-5-[(2-phenylcyclohexyl)methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexyl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-chlorophenyl)cyclohexyl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
2-(2-methoxyethoxy)-5-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexyl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
5-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-fluorophenyl)cyclohexyl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexyl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
2-(2-methoxyethoxy)-5-[[2-(2-methoxypyridin-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-(2-methoxyethoxy)-5-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-(2-methoxyethoxy)-5-[[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-(2-methoxyethoxy)-5-[[2-(2-propylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-chloropyridin-3-yl)cyclohexyl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
2-(2-methoxyethoxy)-5-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-(2-methoxyethoxy)-5-[[2-(2-methoxyphenyl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-(2-methoxyethoxy)-5-[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-ethylpyrazol-3-yl)cyclohexyl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-hydroxybutan-2-yl)cyclohexyl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-hydroxypropan-2-yl)cyclohexyl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-hydroxypentan-2-yl)cyclohexyl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
2-(2-morpholin-4-ylethoxy)-5-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-chlorophenyl)cyclohexyl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
2-(2-morpholin-4-ylethoxy)-54[2-(2-propylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-(2-morpholin-4-ylethoxy)-5-[(2-phenylcyclohexyl)methoxy]pyridine-4-carbaldehyde;
2-(2-morpholin-4-ylethoxy)-5-[[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexyl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-methoxypyridin-3-yl)cyclohexyl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-ethylpyrazol-3-yl)cyclohexyl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
2-(2-morpholin-4-ylethoxy)-5-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexyl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-chloropyridin-3-yl)cyclohexyl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
5-[[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexyl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-fluorophenyl)cyclohexyl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexyl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-methoxyphenyl)cyclohexyl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
2-(2-morpholin-4-ylethoxy)-5-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexyl]methoxy]pyridine-4-carbaldehyde;
2-(2-morpholin-4-ylethoxy)-5-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexyl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-hydroxypentan-2-yl)cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-hydroxybutan-2-yl)cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-hydroxypropan-2-yl)cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-propylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-chloropyridin-3-yl)cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-methoxyphenyl)cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-ethylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-chlorophenyl)cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[(2-phenylcyclohexen-1-yl)methoxy]pyridine-2-carbaldehyde;
3-[[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-fluorophenyl)cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-methoxypyridin-3-yl)cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-hydroxybutan-2-yl)cyclohexen-1-yl]methoxy]-6-methylpyridine-2-carbaldehyde;
3-[[2-(2-hydroxypropan-2-yl)cyclohexen-1-yl]methoxy]-6-methylpyridine-2-carbaldehyde;
3-[[2-(2-hydroxypentan-2-yl)cyclohexen-1-yl]methoxy]-6-methylpyridine-2-carbaldehyde;
3-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-6-methylpyridine-2-carbaldehyde;
3-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-6-methylpyridine-2-carbaldehyde;
6-methyl-3-[[2-(2-propylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-chloropyridin-3-yl)cyclohexen-1-yl]methoxy]-6-methylpyridine-2-carbaldehyde;
6-methyl-3-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-methoxyphenyl)cyclohexen-1-yl]methoxy]-6-methylpyridine-2-carbaldehyde;
6-methyl-3-[[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
6-methyl-3-[[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-[[2-(2-ethylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-6-methylpyridine-2-carbaldehyde;
3-[[2-(2-chlorophenyl)cyclohexen-1-yl]methoxy]-6-methylpyridine-2-carbaldehyde;
6-methyl-3-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
6-methyl-3-[(2-phenylcyclohexen-1-yl)methoxy]pyridine-2-carbaldehyde;
3-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]-6-methylpyridine-2-carbaldehyde;
3-[[2-(2-fluorophenyl)cyclohexen-1-yl]methoxy]-6-methylpyridine-2-carbaldehyde;
3-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-6-methylpyridine-2-carbaldehyde;
3-[[2-(2-methoxypyridin-3-yl)cyclohexen-1-yl]methoxy]-6-methylpyridine-2-carbaldehyde;
6-methyl-3-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-2-carbaldehyde;
3-chloro-5-[[2-(2-hydroxypropan-2-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-hydroxypentan-2-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-hydroxybutan-2-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-methoxyphenyl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-ethylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-chlorophenyl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-fluorophenyl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-methoxypyridin-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-propylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[[2-(2-chloropyridin-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-chloro-5-[(2-phenylcyclohexen-1-yl)methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-hydroxypentan-2-yl)cyclohexen-1-yl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-[[2-(2-hydroxybutan-2-yl)cyclohexen-1-yl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-[[2-(2-hydroxypropan-2-yl)cyclohexen-1-yl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-[[2-(2-methoxyphenyl)cyclohexen-1-yl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-methyl-5-[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-methyl-5-[[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-ethylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-methyl-5-[(2-phenylcyclohexen-1-yl)methoxy]pyridine-4-carbaldehyde;
3-[[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-[[2-(2-fluorophenyl)cyclohexen-1-yl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-[[2-(2-methoxypyridin-3-yl)cyclohexen-1-yl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-methyl-5-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-methyl-5-[[2-(2-propylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-chloropyridin-3-yl)cyclohexen-1-yl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-methyl-5-[[2-(3-propan-2-yhmidazol-4-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-chlorophenyl)cyclohexen-1-yl]methoxy]-5-methylpyridine-4-carbaldehyde;
3-methyl-5-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-hydroxy-5-[[2-(2-hydroxypentan-2-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-hydroxy-5-[[2-(2-hydroxybutan-2-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-hydroxy-5-[[2-(2-hydroxypropan-2-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-hydroxy-5-[[2-(3-propan-2-yhmidazol-4-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]-5-hydroxypyridine-4-carbaldehyde;
3-[[2-(2-fluorophenyl)cyclohexen-1-yl]methoxy]-5-hydroxypyridine-4-carbaldehyde;
3-hydroxy-5-[[2-(2-methoxypyridin-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-hydroxy-5-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-5-hydroxypyridine-4-carbaldehyde;
3-hydroxy-5-[[2-(2-propylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-chloropyridin-3-yl)cyclohexen-1-yl]methoxy]-5-hydroxypyridine-4-carbaldehyde;
3-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-5-hydroxypyridine-4-carbaldehyde;
3-hydroxy-5-[[2-(2-methoxyphenyl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-hydroxy-5-[[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-hydroxy-5-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-hydroxy-5-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-ethylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-5-hydroxypyridine-4-carbaldehyde;
3-[[2-(2-chlorophenyl)cyclohexen-1-yl]methoxy]-5-hydroxypyridine-4-carbaldehyde;
3-hydroxy-5-[(2-phenylcyclohexen-1-yl)methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-5-hydroxypyridine-4-carbaldehyde;
3-[[2-(2-hydroxybutan-2-yl)cyclohexen-1-yl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-[[2-(2-hydroxypropan-2-yl)cyclohexen-1-yl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-[[2-(2-hydroxypentan-2-yl)cyclohexen-1-yl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-[[2-(2-fluorophenyl)cyclohexen-1-yl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-methoxy-5-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-methoxy-5-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-chlorophenyl)cyclohexen-1-yl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-methoxy-5-[[2-(2-propylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-methoxy-5-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-methoxy-5-[(2-phenylcyclohexen-1-yl)methoxy]pyridine-4-carbaldehyde;
3-methoxy-5-[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-methoxy-5-[[2-(2-methoxypyridin-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-ethylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-methoxy-5-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
3-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-[[2-(2-chloropyridin-3-yl)cyclohexen-1-yl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]-5-methoxypyridine-4-carbaldehyde;
3-methoxy-5-[[2-(2-methoxyphenyl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
2-hydroxy-5-[[2-(2-hydroxybutan-2-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
2-hydroxy-5-[[2-(2-hydroxypropan-2-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
2-hydroxy-5-[[2-(2-hydroxypentan-2-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-ethylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-hydroxypyridine-4-carbaldehyde;
5-[[2-(2-chlorophenyl)cyclohexen-1-yl]methoxy]-2-hydroxypyridine-4-carbaldehyde;
2-hydroxy-5-[(2-phenylcyclohexen-1-yl)methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-hydroxypyridine-4-carbaldehyde;
5-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-hydroxypyridine-4-carbaldehyde;
2-hydroxy-5-[[2-(2-methoxypyridin-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
2-hydroxy-5-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-hydroxypyridine-4-carbaldehyde;
2-hydroxy-5-[[2-(2-propylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-chloropyridin-3-yl)cyclohexen-1-yl]methoxy]-2-hydroxypyridine-4-carbaldehyde;
2-hydroxy-5-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
2-hydroxy-5-[[2-(2-methoxyphenyl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
2-hydroxy-5-[[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
2-hydroxy-5-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
2-hydroxy-5-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]-2-hydroxypyridine-4-carbaldehyde;
5-[[2-(2-fluorophenyl)cyclohexen-1-yl]methoxy]-2-hydroxypyridine-4-carbaldehyde;
5-[[2-(2-hydroxypropan-2-yl)cyclohexen-1-yl]methoxy]-2-methoxypyridine-4-carbaldehyde;
5-[[2-(2-hydroxypentan-2-yl)cyclohexen-1-yl]methoxy]-2-methoxypyridine-4-carbaldehyde;
5-[[2-(2-hydroxybutan-2-yl)cyclohexen-1-yl]methoxy]-2-methoxypyridine-4-carbaldehyde;
2-methoxy-5-[[2-(2-methoxypyridin-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-methoxypyridine-4-carbaldehyde;
2-methoxy-5-[[2-(2-propylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-chloropyridin-3-yl)cyclohexen-1-yl]methoxy]-2-methoxypyridine-4-carbaldehyde;
5-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-methoxypyridine-4-carbaldehyde;
2-methoxy-5-[[2-(2-methoxyphenyl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
2-methoxy-5-[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
2-methoxy-5-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
2-methoxy-5-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-ethylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-methoxypyridine-4-carbaldehyde;
5-[[2-(2-chlorophenyl)cyclohexen-1-yl]methoxy]-2-methoxypyridine-4-carbaldehyde;
2-methoxy-5-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
2-methoxy-5-[(2-phenylcyclohexen-1-yl)methoxy]pyridine-4-carbaldehyde;
5-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]-2-methoxypyridine-4-carbaldehyde;
5-[[2-(2-fluorophenyl)cyclohexen-1-yl]methoxy]-2-methoxypyridine-4-carbaldehyde;
5-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-methoxypyridine-4-carbaldehyde;
2-methoxy-5-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-hydroxypropan-2-yl)cyclohexen-1-yl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-hydroxypentan-2-yl)cyclohexen-1-yl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-hydroxybutan-2-yl)cyclohexen-1-yl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
2-(2-methoxyethoxy)-5-[(2-phenylcyclohexen-1-yl)methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-chlorophenyl)cyclohexen-1-yl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
2-(2-methoxyethoxy)-5-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
5-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-fluorophenyl)cyclohexen-1-yl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
2-(2-methoxyethoxy)-5-[[2-(2-methoxypyridin-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
2-(2-methoxyethoxy)-5-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
2-(2-methoxyethoxy)-5-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
2-(2-methoxyethoxy)-5-[[2-(2-propylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-chloropyridin-3-yl)cyclohexen-1-yl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
2-(2-methoxyethoxy)-5-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
2-(2-methoxyethoxy)-5-[[2-(2-methoxyphenyl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
2-(2-methoxyethoxy)-5-[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-ethylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-(2-methoxyethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-hydroxybutan-2-yl)cyclohexen-1-yl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-hydroxypropan-2-yl)cyclohexen-1-yl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-hydroxypentan-2-yl)cyclohexen-1-yl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
2-(2-morpholin-4-ylethoxy)-5-[[2-[2-(3,3,3-trifluoropropyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-chlorophenyl)cyclohexen-1-yl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
2-(2-morpholin-4-ylethoxy)-5-[[2-(2-propylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
2-(2-morpholin-4-ylethoxy)-5-[(2-phenylcyclohexen-1-yl)methoxy]pyridine-4-carbaldehyde;
2-(2-morpholin-4-ylethoxy)-5[[2-[2-(2,2,2-trifluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-cyclobutylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-methoxypyridin-3-yl)cyclohexen-1-yl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-ethylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
2-(2-morpholin-4-ylethoxy)-5-[[2-(2-propan-2-ylpyrazol-3-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
5-[[2-(2-cyclopentylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-chloropyridin-3-yl)cyclohexen-1-yl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
5-[[2-[2-(2,2-difluoroethyl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-fluorophenyl)cyclohexen-1-yl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-cyclopropylpyrazol-3-yl)cyclohexen-1-yl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
5-[[2-(2-methoxyphenyl)cyclohexen-1-yl]methoxy]-2-(2-morpholin-4-ylethoxy)pyridine-4-carbaldehyde;
2-(2-morpholin-4-ylethoxy)-5-[[2-[2-(oxetan-3-yl)pyrazol-3-yl]cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde;
and
2-(2-morpholin-4-ylethoxy)-5-[[2-(3-propan-2-ylimidazol-4-yl)cyclohexen-1-yl]methoxy]pyridine-4-carbaldehyde,
or a tautomer, a stereoisomer, a mixture of stereoisomers, or a pharmaceutically acceptable salt thereof.

567 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/776,723Filed 14 Mar 2014 · us provisional application
Priority: 15 Mar 2013
Published: US 2016/0039801 A111 Feb 2016
Granted: 16 Oct 2018
Term ends: Not estimatedThe source records don’t support an estimate.

Classification22 codes

C07D 405/14
Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having…:…
A61P 7/00
Drugs for disorders of the blood or the extracellular fluid
C07C 47/565
Containing hydroxy groups: all hydroxy groups bound to the ring
C07C 47/575
Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings: containing ether groups, [IMAGE cpc-sch-C07C-0958.gif]…

Family

Application61/799,120Us provisional application · filed 15 Mar 2013
US 2016/0039801 A1Pre-grant publication · published 11 Feb 2016
US 10,100,043 B2This patent

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

Timeline

Citations

Open elsewhere

patentgrep

Loading patent…

Abstract

A compound of Formula (I):

a tautomer, a stereoisomer, a mixture of stereoisomers, or a pharmaceutically acceptable salt thereof, wherein:
Q is cycloalkyl or cycloalkenyl, each of which is substituted with one to three Ra;
Y is CR1aR1b, wherein
R1a is H or halo, and
R1b is H or halo;
X is 0;
T1, T2, T3, and T4 are independently C or N provided that at least one of T1, T2, T3, and T4 is C;
wherein when T1, T2, T3, or T4 are N, then R2, R3, R4, or R5, respectively, are absent;
R2, R3, and R4 are independently hydrogen, halo, Rb, ORd, or NRdNRd;
R5 is selected from the group consisting of hydrogen, halo, Rb, ORd, —O(CH2)zORd, —O(CH2)zNRdRd, OC(O)Re, SRd, CN, NO2, CO2Rd, CONRdRd, C(O)Rd, OC(O)NRdRd, NRdRd, NRdC(O)Re, NRdC(O)2Re, NRdC(O)NRdRd, S(O)Re, S(O)2Re, NRdS(O)2Re, S(O)2NRdRd, and N3;
wherein z is 0, 1, 2, 3, 4, 5, or 6;
or
R5 is —(CH2)pR5a, wherein p is 0 or 1 and R5a is OH;
R6 and R7 together form oxo or an aldehyde protecting group, or
R6 together with R1b or R5 forms a cyclic ether, wherein
one of R1b or R5a is O, R6 is a bond, and
R7 is selected from the group consisting of OH, C1-8alkoxy, and haloC1-8alkoxy;
each Ra is independently selected from the group consisting of halo, Rb, ORd, —(CH2)kCO2(C1-8alkyl)OH, —(CH2)kCO2Rd, —(CH2)kCONRdRd, —(CH2)kC(O)Rd, —(CH2)karyl optionally substituted with one to three Rc, —(CH2)kheteroaryl optionally substituted with one to three Rc, and —(CH2)kheterocycloalkyl optionally substituted with one to three Rc ;
wherein k is 0, 1, 2, 3, 4, 5, or 6;
and wherein at least one of Ra is selected from the group consisting of ORd, —(CH2)kCO2(C1-8alkyl)OH, —(CH2)kCO2Rd, —(CH2)kCONRdRd, —(CH2)kC(O)Rd, —(CH2)karyl optionally substituted with one to three Rc, —(CH2)kheteroaryl optionally substituted with one to three Rc, —(CH2)kheterocycloalkyl optionally substituted with one to three Rc, substituted C1-8alkyl, substituted C2-8alkenyl, and substituted C2-8 alkynyl;
wherein the substituted C1-8alkyl, substituted C2-8alkenyl, and substituted C2-8 alkynyl are each substituted with one to three halo, ORd, or NRdRd;
each Rb is independently selected from the group consisting of C1-8alkyl, C2-8alkenyl, and C2-8 alkynyl, each optionally independently substituted with one to three halo, ORd, or NRdRd;
each Rc is independently selected from the group consisting of halo, C1-8alkyl, haloC1-8alkyl, C2-8alkenyl, haloC2-8 alkenyl, C2-8alkynyl, haloC2-8alkynyl, (CH2)mORf, heteroaryl, cycloalkyl, and heterocycloalkyl;
wherein m is selected from the group consisting of 0, 1, 2, 3, 4, 5, and 6;
each Rd is independently selected from the group consisting of hydrogen, C1-8 alkyl, haloC1-8alkyl, C2-8 alkenyl, haloC2-8alkenyl, C2-8 alkynyl, haloC2-8alkynyl, —(CH2)kheterocycloalkyl, and —(CH2)uO—(CH2)uH;
wherein k is 0, 1, 2, 3, 4, 5, or 6 and each u is independently 1, 2, 3, 4, 5, or 6;
each Rf is independently selected from the group consisting of hydrogen, C1-8 alkyl, haloC1-8alkyl, C2-8 alkenyl, haloC2-8alkenyl, C2-8 alkynyl, and haloC2-8alkynyl;
and
Re is C1-8alkyl, haloC1-8alkyl, C2-8 alkenyl, haloC2-8alkenyl, C2-8alkynyl, or haloC2-8alkynyl;
provided that:
at least one of R4 and R5 is other than hydrogen or
T1 and T3 are C;
T2 is N and T4 is C, or T2 is C and T4 is N.

30 more elements

Facts

Application

14/776,723Filed 14 Mar 2014 · us provisional application

Priority

15 Mar 2013

Published

US 2016/0039801 A111 Feb 2016

Granted

16 Oct 2018

Term ends

Not estimatedThe source records don’t support an estimate.

Classification22 codes

C07D 405/14
Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having…:…
A61P 7/00
Drugs for disorders of the blood or the extracellular fluid
C07C 47/565
Containing hydroxy groups: all hydroxy groups bound to the ring
C07C 47/575
Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings: containing ether groups, [IMAGE cpc-sch-C07C-0958.gif]…