US 2012/0238565 A1Published application

Triazolopyridine compounds and their use as ask inhibitors

AssigneeMerck Serono SA

InventorsDOMINIQUE SWINNEN, Catherine Jorand-Lebrun, Tania Grippi-Vallotton, Mathilde Muzerelle, Amanda Royle, Jacqueline Macritchie, Richard Hill, Jeffrey P. Shaw

Life of this patent

Estimating the term…

Abstract

The present invention relates to triazolopyridine compounds according to Formula (I), their use as medicament, for treating autoimmune disorders, inflammatory diseases, cardiovascular diseases and/or neurodegenerative diseases and a process for their preparation.

Claims10

Dependent claims

A triazolopyridine compound of formula I:

Formula (I)
wherein:
R1 is selected from:
a) —NR6R7;
b) C3-C8-cycloalkoxy, or C1-C6-alkoxy;
c) C3-C8-cycloalkyl sulfanyl, or C1-C6-alkyl sulfanyl;
or
d) 5 or 6-membered heteroaryl having at least one heteroatom selected from N, S or O, said heteroaryl being substituted with C1-C6 alkyl, halogen, or C1-C6 alkoxy;
R2 is selected from:
a) hydrogen;
b) halogen;
c) aryl that is unsubstituted or is substituted with R10, R11 and/or R12;
or
d) 5 to 10-membered heteroaryl having at least one heteroatom selected from N, S or O and wherein said 5 to 10-membered heteroaryl is unsubstituted or is substituted with C1-C6 alkyl;
or R1 and R2 taken together form a —C═C—C═C— group-;
R3 is selected from:
a) hydrogen;
b) halogen;
or
c) C1-C6-alkyl that is unsubstituted or is substituted with at least one fluoro;
R4 is selected from:
a) hydrogen;
or
b) 5 or 6-membered heteroaryl having at least one heteroatom selected from N, S or O;
R5 is selected from:
a) C1-C6-alkyl that is unsubstituted or is substituted with at least one of the following groups:
i) alkoxycarbonyl,
ii) C1-C6-alkoxy,
iii) —NC(O)R′ wherein R′ is an aryl that is unsubstituted or is substituted with C1-C6-alkyl, or
iv) benzyloxy;
b) aryl-C1-C6-alkyl;
c) 5 or 6-membered heteroaryl-C1-C6-alkyl having a heteroatom selected from N, S or O that is unsubstituted or is substituted with C1-C6-alkyl, halogen or C1-C6-alkoxy;
d) C3-C6-cycloalkyl that is substituted with phenyl;
e) 3 to 8-membered heterocycloalkyl having a heteroatom selected from N, S or O that is substituted with an acyl group;
f) aryl that is unsubstituted or is substituted with at least one of the following groups:
i) C1-C6-alkyl,
ii) halogen,
iii) C1-C6-alkoxy,
iv) perfluoro-C1-C6-alkyl,
v) at least one C1-C6-alkoxy that is unsubstituted or is substituted with C1-C6-alkoxy carbonyl,
vi) phenyl,
vii) C1-C6-alkyl sulfonyl,
viii) —NHC(O)C1-C6-alkyl,
ix) amino-C1-C6-alkyl wherein amino is selected from —NH2, —NHC1-C6-alkyl, —N(C1-C6-alkyl)2, N(C1-C6-alkyl)(C1-C6-alkoxy-C1-C6-alkyl), and the two substituents C1-C6-alkyl can be the same or different, and wherein the two substituents may form a 3 to 8-membered heterocycloalkyl with the N to which they are attached and wherein the heterocycloalkyl is unsubstituted or is substituted with C1-C6-alkyl or with hydroxy,
x) —N(C1-C6-alkyl) (C1-C6-alkoxy-C1-C6-alkyl),
xi) 5 to 6-membered heterocycloalkyl-C1-C6-alkyl having a heteroatom selected from N and O, or
xii) amido-C1-C6-alkyl;
g) 5 to 10-membered heteroaryl having at least one heteroatom selected from N, O or S optionally substituted with halogen;
or
h) pyridinyl that is unsubstituted or is substituted with at least one of the following groups:
i) halogen,
ii) C1-C6-alkyl,
iii) amino-C1-C6-alkyl wherein amino is selected from —NH2, —NHC1-C6-alkyl or —N(C1-C6-alkyl)2, wherein the two substituents C1-C6-alkyl can be the same or different, and wherein the two substituents may form a 3 to 8-membered heterocycloalkyl with the N to which they are attached and wherein the heterocycloalkyl is unsubstituted or is substituted with C1-C6-alkyl or hydroxy,
iv) —NH(hydroxy-C1-C6-alkyl),
v) —NH-(5-membered heteroaryl-C1-C6-alkyl having as heteroatom O),
vi) 5 or 6-membered heterocycloalkyl-C1-C6-alkyl having at least one heteroatom selected from O or N,
vii) 5 or 6-membered heterocycloalkyl having at least one heteroatom selected from O or N and that is unsubstituted or is substituted with hydroxy, —C(O)OR′ wherein R′ is C1-C6-alkyl, halogen or C1-C6-alkyl,
viii) amino,
ix) —NH(amino-C1-C6-alkyl), or
x) —N(C1-C6-alkyl)2;
R6 is selected from:
a) C1-C6-alkyl that is unsubstituted or is substituted with one or two hydroxy groups;
b) phenyl substituted with at least one of the following groups:
i) halogen,
ii) C1-C6-alkyl, or
iii) C1-C6-alkoxy;
c) 5 or 6-membered heterocycloalkyl having a heteroatom selected from O or N and substituted with C1-C6-alkyl;
d) C3-C8-cycloalkyl substituted with R8;
or
e) —(CH2)nR9 wherein n equals 1, 2 or 3;
R7 is:
a) hydrogen;
or
b) C1-C6-alkyl;
or R6 and R7 can form a 3 to 8-membered heterocycloalkyl with the N to which they are attached and wherein the heterocycloalkyl is substituted with C1-C6-alkyl;
R8 is selected from:
a) hydrogen;
b) hydroxy;
c) C1-C6-alkyl that is unsubstituted or is substituted with hydroxy;
d) C(O)O—C1-C6-alkyl;
or
e) —NH2;
R9 is selected from:
a) C3-C8-cycloalkyl that is unsubstituted or is substituted with an unsubstituted C1-C6-alkyl;
b) 5 or 6-membered heterocycloalkyl having a heteroatom selected from N and O and that is unsubstituted or is substituted with C1-C6-alkyl;
c) 5 or 6-membered heteroaryl having a heteroatom selected from N and O that is unsubstituted or is and that is unsubstituted or is substituted with C1-C6-alkyl;
or
d) phenyl;
and
R10, R11 and R12 are each independently selected from:
a) hydrogen;
b) halogen;
c) hydroxy;
d) C1-C6-alkyl;
e) C1-C6-alkoxy;
f) cyano;
g) —C(O)NH(C1-C6-alkyl)amino wherein the amino is —N(CH3)2);
or
h) —NH2.

96 more elements

A triazolopyridine compound selected from:

N-[5-(cyclopropylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-(5-pyrrolidin-1-yl[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide;
N-[1,2,4]triazolo[1,5-a]quinolin-2-ylnicotinamide;
N-[5-(cyclopentylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]benzamide;
N-{5-[(3-methoxypropyl)amino][1,2,4]triazolo[1,5-a]pyridin-2-yl}benzamide;
N-{5-[(2-furylmethyl)amino][1,2,4]triazolo[1,5-a]pyridin-2-yl}benzamide;
N-{5-[(tetrahydrofuran-2-ylmethyl)amino][1,2,4]triazolo[1,5-a]pyridin-2-yl}benzamide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]benzamide;
N-(5-{[1-(hydroxymethyl)propyl]amino}[1,2,4]triazolo[1,5-a]pyridin-2-yl)benzamide;
N-{5-[(2-methoxyethyl)amino][1,2,4]triazolo[1,5-a]pyridin-2-yl}benzamide;
N-{5-[(2,3-dihydroxypropyl)amino][1,2,4]triazolo[1,5-a]pyridin-2-yl}benzamide;
N-[5-(benzylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-(cycloheptylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide dihydrochloride;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-(5-{[(5-methyl-2-furyl)methyl]amino}[1,2,4]triazolo[1,5-a]pyridin-2-yl)nicotinamide;
N-{5-[(tetrahydrofuran-2-ylmethyl)amino][1,2,4]triazolo[1,5-a]pyridin-2-yl}nicotinamide;
N-[5-(cyclooctylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-{5-[cyclohexyl(methyl)amino][1,2,4]triazolo[1,5-a]pyridin-2-yl}nicotinamide;
N-[5-(tetrahydro-2H-pyran-4-ylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-{5-[(1-methylpiperidin-4-yl)amino][1,2,4]triazolo[1,5-a]pyridin-2-yl}nicotinamide;
N-{5-[(3-aminocyclohexyl)amino][1,2,4]triazolo[1,5-a]pyridin-2-yl}benzamide;
N-{5-[(1-methylpiperidin-4-yl)amino][1,2,4]triazolo[1,5-a]pyridin-2-yl}benzamide;
N-[5-(cyclopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-(cyclohexylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-(cycloheptylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-(cyclopentylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-[(cyclohexylmethyl)amino]-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-{5-[(3-hydroxycyclohexyl)amino][1,2,4]triazolo[1,5-a]pyridin-2-yl}nicotinamide;
N-{5-[(4-tert-butylcyclohexyl)amino][1,2,4]triazolo[1,5-a]pyridin-2-yl}nicotinamide;
N-[5-(tetrahydro-2H-pyran-3-ylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]benzamide;
N-[5-(cycloheptylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-(morpholin-4-ylmethyl)benzamide;
N-[5-(cyclohexylthio)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-{5-[(trans-4-hydroxycyclohexyl)amino][1,2,4]triazolo[1,5-a]pyridin-2-yl}nicotinamide;
N-[5-(cyclobutylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-morpholin-4-ylnicotinamide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-[(dimethylamino)methyl]benzamide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-3-(morpholin-4-ylmethyl)benzamide;
N-[5-[(cyclopropylmethyl)amino]-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
methyltrans-4-{[2-[(pyridin-3-ylcarbonyl)amino]-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-5-yl]amino}cyclohexanecarboxylate;
N-[5-{[(1RS,2RS)-2-(hydroxymethyl)cyclohexyl]amino}-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[6-bromo-5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-(cycloheptylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]tetrahydro-2H-pyran-4-carboxamide;
N-(3-{[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino}-3-oxopropyl)benzamide;
N-[5-(isopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-(sec-butylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-(methylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-(cyclohexyloxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-2-(3-methoxyphenyl)acetamide;
N-[5-(cyclohexyloxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-(2-pyrrolidin-1-ylethyl)nicotinamide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-(morpholin-4-ylmethyl)nicotinamide;
N-{5-[(cyclohexylmethyl)amino][1,2,4]triazolo[1,5-a]pyridin-2-yl}nicotinamide;
N-{5-[(4-hydroxycyclohexyl)amino][1,2,4]triazolo[1,5-a]pyridin-2-yl}-3-methoxybenz amide;
N-[5-(cyclopentylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-2-furamide;
N-[7-chloro-5-(cyclobutylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[7-chloro-5-(cyclopentylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[7-chloro-5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-(sec-butylamino)-7-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[7-chloro-5-(cyclopropylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-[(2-methoxyethyl)amino]-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-[(3-hydroxypropyl)amino]-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-[(2-hydroxyethyl)amino]-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-(dimethylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-2-pyridin-3-ylacetamide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-(piperidin-1-ylmethyl)benzamide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-(pyrrolidin-1-ylmethyl)benzamide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-{[(2-methoxyethyl)(methyl)amino]methyl}benzamide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-methylnicotinamide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-[(3-hydroxypropyl)amino]nicotinamide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-[(2-furylmethyl)amino]nicotinamide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide 1-oxide;
N-[5-(isopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-2-pyridin-3-ylacetamide trihydrochloride;
N-[5-[(1-ethylpropyl)amino]-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-(isopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide 1-oxide;
N-[5-[(3-hydroxycyclohexyl)amino]-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide formic acid;
N-{7-chloro-5-[(3-hydroxycyclohexyl)amino][1,2,4]triazolo[1,5-a]pyridin-2-yl}nicotinamide formic acid;
N-[5-(cyclopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-[(dimethylamino)methyl]benzamide;
N-[5-(cyclopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-[(2-oxopyrrolidin-1-yl)methyl]benzamide;
N-[5-(cyclopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-pyrrolidin-1-ylnicotinamide;
N-[5-(cyclopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-methylnicotinamide;
N-[5-{[(1R,2S)-2-(hydroxymethyl)cyclohexyl]amino}-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide hydrochloride;
N-[5-(cyclopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-[(4-hydroxypiperidin-1-yl)methyl]benzamide;
N-[5-(cyclopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-(pyrrolidin-1-ylmethyl)benzamide;
N-[5-(cyclopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-(4-hydroxypiperidin-1-yl)nicotinamide;
N-[5-(cyclopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-piperazin-1-ylnicotinamide;
N-[5-(cyclopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-(dimethylamino)nicotinamide;
N-[6-bromo-5-(cyclopentylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-morpholin-4-ylnicotinamide;
N-[5-(cyclopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-morpholin-4-ylnicotinamide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-(dimethylamino)nicotinamide;
tert-butyl 4-[5-({[5-(cyclopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino}carbonyl)pyridin-2-yl]piperazine-1-carboxylate;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-[(4-hydroxypiperidin-1-yl)methyl]benz amide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-(4-fluoropiperidin-1-yl)nicotinamide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-(1H-pyrazol-1-yl)nicotinamide;
tert-butyl 4-[5-({[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]amino}carbonyl)pyridin-2-yl]piperazine-1-carboxylate;
N-[5-(cyclopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-[(3-hydroxypropyl)amino]nicotinamide;
N-[5-(isopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-(morpholin-4-ylmethyl)nicotinamide;
N-[5-[(pyrrolidin-3-ylmethyl)amino]-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-(piperazin-1-ylmethyl)benzamide;
N-[5-(cyclohexylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-[(4-formylpiperazin-1-yl)methyl]benz amide;
N-[5-(piperidin-3-ylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-(sec-butylamino)-7-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-[(2-methoxyethyl)(methyl)amino]nicotinamide;
N-[5-(sec-butylamino)-7-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-[(3-hydroxypropyl)amino]nicotinamide;
N-[5-(sec-butylamino)-7-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-morpholin-4-ylnicotinamide;
N-[5-(sec-butylamino)-7-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-{[(2-methoxyethyl)(methyl)amino]methyl}benzamide;
N-[5-(sec-butylamino)-7-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-methylnicotinamide;
N-[7-chloro-5-(isopropylamino)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-[(3-isopropoxyphenyl)amino]-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-[(3-fluoro-4-methoxyphenyl)amino]-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-{[3-(benzyloxy)phenyl]amino}-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-(sec-butylamino)-7-chloro[1,2,4]triazolo[1,5-a]pyridin-2-yl]-4-(morpholin-4-ylmethyl)benzamide;
N-[5-(isopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]-6-methylnicotinamide;
6-chloro-N-[5-(isopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
6-[(2-aminoethyl)amino]-N-[5-(isopropylamino)-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
N-[5-(sec-butylamino)-7-methyl[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide;
or
N-[5-(isopropylamino)-7-methyl[1,2,4]triazolo[1,5-a]pyridin-2-yl]nicotinamide.

112 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/483,324Filed 30 May 2012
Priority: EP 07115408.231 Aug 2007
Published: 20 Sep 2012
Term ends: Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07D 471/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 9/00
Drugs for disorders of the cardiovascular system
A61P 9/10
Drugs for disorders of the cardiovascular system: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary…
A61P 25/28
Drugs for disorders of the nervous system: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents,…

Family

Application60/966,989Us provisional application · filed 31 Aug 2007
Application12/666,445Continuation · filed 23 Dec 2009
Application13/483,324Continuation
US 2010/0197681 A1Published application
US 8,263,595 B2Related patent
US 2012/0238565 A1This patent

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

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Abstract

A triazolopyridine compound of formula I:

Formula (I)
wherein:
R1 is selected from:
a) —NR6R7;
b) C3-C8-cycloalkoxy, or C1-C6-alkoxy;
c) C3-C8-cycloalkyl sulfanyl, or C1-C6-alkyl sulfanyl;
or
d) 5 or 6-membered heteroaryl having at least one heteroatom selected from N, S or O, said heteroaryl being substituted with C1-C6 alkyl, halogen, or C1-C6 alkoxy;
R2 is selected from:
a) hydrogen;
b) halogen;
c) aryl that is unsubstituted or is substituted with R10, R11 and/or R12;
or
d) 5 to 10-membered heteroaryl having at least one heteroatom selected from N, S or O and wherein said 5 to 10-membered heteroaryl is unsubstituted or is substituted with C1-C6 alkyl;
or R1 and R2 taken together form a —C═C—C═C— group-;
R3 is selected from:
a) hydrogen;
b) halogen;
or
c) C1-C6-alkyl that is unsubstituted or is substituted with at least one fluoro;
R4 is selected from:
a) hydrogen;
or
b) 5 or 6-membered heteroaryl having at least one heteroatom selected from N, S or O;
R5 is selected from:
a) C1-C6-alkyl that is unsubstituted or is substituted with at least one of the following groups:
i) alkoxycarbonyl,
ii) C1-C6-alkoxy,
iii) —NC(O)R′ wherein R′ is an aryl that is unsubstituted or is substituted with C1-C6-alkyl, or
iv) benzyloxy;
b) aryl-C1-C6-alkyl;
c) 5 or 6-membered heteroaryl-C1-C6-alkyl having a heteroatom selected from N, S or O that is unsubstituted or is substituted with C1-C6-alkyl, halogen or C1-C6-alkoxy;
d) C3-C6-cycloalkyl that is substituted with phenyl;
e) 3 to 8-membered heterocycloalkyl having a heteroatom selected from N, S or O that is substituted with an acyl group;
f) aryl that is unsubstituted or is substituted with at least one of the following groups:
i) C1-C6-alkyl,
ii) halogen,
iii) C1-C6-alkoxy,
iv) perfluoro-C1-C6-alkyl,
v) at least one C1-C6-alkoxy that is unsubstituted or is substituted with C1-C6-alkoxy carbonyl,
vi) phenyl,
vii) C1-C6-alkyl sulfonyl,
viii) —NHC(O)C1-C6-alkyl,
ix) amino-C1-C6-alkyl wherein amino is selected from —NH2, —NHC1-C6-alkyl, —N(C1-C6-alkyl)2, N(C1-C6-alkyl)(C1-C6-alkoxy-C1-C6-alkyl), and the two substituents C1-C6-alkyl can be the same or different, and wherein the two substituents may form a 3 to 8-membered heterocycloalkyl with the N to which they are attached and wherein the heterocycloalkyl is unsubstituted or is substituted with C1-C6-alkyl or with hydroxy,
x) —N(C1-C6-alkyl) (C1-C6-alkoxy-C1-C6-alkyl),
xi) 5 to 6-membered heterocycloalkyl-C1-C6-alkyl having a heteroatom selected from N and O, or
xii) amido-C1-C6-alkyl;
g) 5 to 10-membered heteroaryl having at least one heteroatom selected from N, O or S optionally substituted with halogen;
or
h) pyridinyl that is unsubstituted or is substituted with at least one of the following groups:
i) halogen,
ii) C1-C6-alkyl,
iii) amino-C1-C6-alkyl wherein amino is selected from —NH2, —NHC1-C6-alkyl or —N(C1-C6-alkyl)2, wherein the two substituents C1-C6-alkyl can be the same or different, and wherein the two substituents may form a 3 to 8-membered heterocycloalkyl with the N to which they are attached and wherein the heterocycloalkyl is unsubstituted or is substituted with C1-C6-alkyl or hydroxy,
iv) —NH(hydroxy-C1-C6-alkyl),
v) —NH-(5-membered heteroaryl-C1-C6-alkyl having as heteroatom O),
vi) 5 or 6-membered heterocycloalkyl-C1-C6-alkyl having at least one heteroatom selected from O or N,
vii) 5 or 6-membered heterocycloalkyl having at least one heteroatom selected from O or N and that is unsubstituted or is substituted with hydroxy, —C(O)OR′ wherein R′ is C1-C6-alkyl, halogen or C1-C6-alkyl,
viii) amino,
ix) —NH(amino-C1-C6-alkyl), or
x) —N(C1-C6-alkyl)2;
R6 is selected from:
a) C1-C6-alkyl that is unsubstituted or is substituted with one or two hydroxy groups;
b) phenyl substituted with at least one of the following groups:
i) halogen,
ii) C1-C6-alkyl, or
iii) C1-C6-alkoxy;
c) 5 or 6-membered heterocycloalkyl having a heteroatom selected from O or N and substituted with C1-C6-alkyl;
d) C3-C8-cycloalkyl substituted with R8;
or
e) —(CH2)nR9 wherein n equals 1, 2 or 3;
R7 is:
a) hydrogen;
or
b) C1-C6-alkyl;
or R6 and R7 can form a 3 to 8-membered heterocycloalkyl with the N to which they are attached and wherein the heterocycloalkyl is substituted with C1-C6-alkyl;
R8 is selected from:
a) hydrogen;
b) hydroxy;
c) C1-C6-alkyl that is unsubstituted or is substituted with hydroxy;
d) C(O)O—C1-C6-alkyl;
or
e) —NH2;
R9 is selected from:
a) C3-C8-cycloalkyl that is unsubstituted or is substituted with an unsubstituted C1-C6-alkyl;
b) 5 or 6-membered heterocycloalkyl having a heteroatom selected from N and O and that is unsubstituted or is substituted with C1-C6-alkyl;
c) 5 or 6-membered heteroaryl having a heteroatom selected from N and O that is unsubstituted or is and that is unsubstituted or is substituted with C1-C6-alkyl;
or
d) phenyl;
and
R10, R11 and R12 are each independently selected from:
a) hydrogen;
b) halogen;
c) hydroxy;
d) C1-C6-alkyl;
e) C1-C6-alkoxy;
f) cyano;
g) —C(O)NH(C1-C6-alkyl)amino wherein the amino is —N(CH3)2);
or
h) —NH2.

96 more elements

Facts

Application

13/483,324Filed 30 May 2012

Priority

EP 07115408.231 Aug 2007

Published

20 Sep 2012

Term ends

Not estimatedThe source records don’t support an estimate.

Classification9 codes

C07D 471/04
In which the condensed system contains two hetero rings: ortho-condensed systems
A61P 9/00
Drugs for disorders of the cardiovascular system
A61P 9/10
Drugs for disorders of the cardiovascular system: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary…
A61P 25/28
Drugs for disorders of the nervous system: for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents,…

Family

Application60/966,989Us provisional application · filed 31 Aug 2007

Application12/666,445Continuation · filed 23 Dec 2009

Application13/483,324Continuation

US 2010/0197681 A1Published application

US 8,263,595 B2Related patent

US 2012/0238565 A1This patent

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