CA2584248A1

CA2584248A1 - Procede pour traiter des lesions vasculaires

Procede pour traiter des lesions vasculaires Download PDF

Info

Publication number: CA2584248A1
Authority: CA; Canada
Prior art keywords: pyridin; methyl; imidazol; benzo; dioxol
Prior art date: 2004-10-15
Legal status : Abandoned

Application number

CA002584248A

Other languages

English (en)

Inventor

Leona E. Ling

Kai Fu

Alan Gill

Philip J. Gotwals

Current Assignee

Biogen MA Inc

Original Assignee

Individual

Priority date

2004-10-15

Filing date

2005-10-13

Publication date

2006-04-27

2005-10-13 Application filed by Individual filed Critical Individual

2006-04-27 Publication of CA2584248A1 publication Critical patent/CA2584248A1/fr

Status Abandoned legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims description 51
208000024248 Vascular System injury Diseases 0.000 title description 5
208000012339 Vascular injury Diseases 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 83
208000032594 Vascular Remodeling Diseases 0.000 claims abstract description 27
206010020772 Hypertension Diseases 0.000 claims abstract description 26
206010072810 Vascular wall hypertrophy Diseases 0.000 claims abstract description 20
208000037803 restenosis Diseases 0.000 claims abstract description 16
210000000056 organ Anatomy 0.000 claims abstract description 11
208000019553 vascular disease Diseases 0.000 claims abstract description 9
230000002093 peripheral effect Effects 0.000 claims abstract description 7
208000002815 pulmonary hypertension Diseases 0.000 claims abstract description 4
206010042957 Systolic hypertension Diseases 0.000 claims abstract description 3
208000007530 Essential hypertension Diseases 0.000 claims abstract 2
201000004239 Secondary hypertension Diseases 0.000 claims abstract 2
125000000217 alkyl group Chemical group 0.000 claims description 336
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 321
125000000753 cycloalkyl group Chemical group 0.000 claims description 270
-1 hydroxy, amino, nitro, oxo, thioxo Chemical group 0.000 claims description 269
125000001072 heteroaryl group Chemical group 0.000 claims description 231
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 211
125000003118 aryl group Chemical group 0.000 claims description 161
125000003545 alkoxy group Chemical group 0.000 claims description 149
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 149
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 147
125000004414 alkyl thio group Chemical group 0.000 claims description 125
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 122
125000003342 alkenyl group Chemical group 0.000 claims description 118
125000000304 alkynyl group Chemical group 0.000 claims description 103
125000002252 acyl group Chemical group 0.000 claims description 95
125000003710 aryl alkyl group Chemical group 0.000 claims description 89
125000004104 aryloxy group Chemical group 0.000 claims description 86
125000005553 heteroaryloxy group Chemical group 0.000 claims description 86
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 83
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 83
125000000000 cycloalkoxy group Chemical group 0.000 claims description 82
125000005843 halogen group Chemical group 0.000 claims description 80
125000004475 heteroaralkyl group Chemical group 0.000 claims description 79
229910052739 hydrogen Inorganic materials 0.000 claims description 78
239000001257 hydrogen Substances 0.000 claims description 78
125000004093 cyano group Chemical group *C#N 0.000 claims description 77
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 76
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 75
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 75
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 74
125000003435 aroyl group Chemical group 0.000 claims description 72
150000002431 hydrogen Chemical class 0.000 claims description 71
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 68
239000004202 carbamide Substances 0.000 claims description 68
125000005163 aryl sulfanyl group Chemical group 0.000 claims description 65
125000005171 cycloalkylsulfanyl group Chemical group 0.000 claims description 65
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 65
125000005224 heteroarylcarbonylamino group Chemical group 0.000 claims description 54
125000004658 aryl carbonyl amino group Chemical group 0.000 claims description 53
125000000392 cycloalkenyl group Chemical group 0.000 claims description 49
125000004122 cyclic group Chemical group 0.000 claims description 47
125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 47
239000003112 inhibitor Substances 0.000 claims description 43
125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 35
125000005419 heteroarylsulfonylamino group Chemical group 0.000 claims description 35
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 34
125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 33
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
125000005126 aryl alkyl carbonyl amino group Chemical group 0.000 claims description 29
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 29
125000005169 cycloalkylcarbonylamino group Chemical group 0.000 claims description 28
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
229910052757 nitrogen Inorganic materials 0.000 claims description 25
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 24
150000001204 N-oxides Chemical class 0.000 claims description 23
150000003839 salts Chemical class 0.000 claims description 23
125000005018 aryl alkenyl group Chemical group 0.000 claims description 20
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 19
125000001188 haloalkyl group Chemical group 0.000 claims description 18
125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 15
125000004043 oxo group Chemical group O=* 0.000 claims description 13
125000000623 heterocyclic group Chemical group 0.000 claims description 11
125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 11
SARWAMFCNRRZTD-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-piperidin-4-yl-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCNCC2)C=2C=C3OCOC3=CC=2)=N1 SARWAMFCNRRZTD-UHFFFAOYSA-N 0.000 claims description 10
MQZAFVXXIGNUPG-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)pyrazolo[1,5-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C=2C(=C3C=CC=CN3N=2)C=2N=C(N)N=CC=2)=N1 MQZAFVXXIGNUPG-UHFFFAOYSA-N 0.000 claims description 10
125000004450 alkenylene group Chemical group 0.000 claims description 10
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 10
125000004419 alkynylene group Chemical group 0.000 claims description 10
150000001408 amides Chemical class 0.000 claims description 10
125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 10
125000005015 aryl alkynyl group Chemical group 0.000 claims description 10
125000005135 aryl sulfinyl group Chemical group 0.000 claims description 10
VYMTWHZMUYWTDG-UHFFFAOYSA-N benzyl 3-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]piperidine-1-carboxylate Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CN(CCC2)C(=O)OCC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 VYMTWHZMUYWTDG-UHFFFAOYSA-N 0.000 claims description 10
HJTDQRHNNVDYNJ-UHFFFAOYSA-N benzyl 4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]piperidine-1-carboxylate Chemical compound C1CC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CCN1C(=O)OCC1=CC=CC=C1 HJTDQRHNNVDYNJ-UHFFFAOYSA-N 0.000 claims description 10
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 10
125000005149 cycloalkylsulfinyl group Chemical group 0.000 claims description 10
125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 10
OOBORGGKBQGOQB-UHFFFAOYSA-N n-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]acetamide Chemical compound CC(=O)NC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 OOBORGGKBQGOQB-UHFFFAOYSA-N 0.000 claims description 10
125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims description 10
QQXSDZAMXCQBPE-UHFFFAOYSA-N benzyl 3-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]pyrrolidine-1-carboxylate Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CN(CC2)C(=O)OCC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 QQXSDZAMXCQBPE-UHFFFAOYSA-N 0.000 claims description 9
KOJILNLSRNSDPE-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylic acid Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(O)=O)C=2C=C3OCOC3=CC=2)=N1 KOJILNLSRNSDPE-UHFFFAOYSA-N 0.000 claims description 8
KLLKKKAXFTYAGU-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxylic acid Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C(O)=O)C=2N=C(N)N=CC=2)=N1 KLLKKKAXFTYAGU-UHFFFAOYSA-N 0.000 claims description 8
QAALUNOPVWULBE-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxylic acid Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(O)=O)C=2N=C(N)N=CC=2)=N1 QAALUNOPVWULBE-UHFFFAOYSA-N 0.000 claims description 7
YURRESDVZOTIIE-UHFFFAOYSA-N 1-[5-(6-methylpyridin-2-yl)-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylic acid Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(O)=O)C2=CN3N=CN=C3C=C2)=N1 YURRESDVZOTIIE-UHFFFAOYSA-N 0.000 claims description 6
101001053401 Arabidopsis thaliana Acid beta-fructofuranosidase 3, vacuolar Proteins 0.000 claims description 6
101001053395 Arabidopsis thaliana Acid beta-fructofuranosidase 4, vacuolar Proteins 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000006574 non-aromatic ring group Chemical group 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
TWFAJNXORPXXHJ-UHFFFAOYSA-N (2-chlorophenyl)methyl 4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]piperidine-1-carboxylate Chemical compound ClC1=CC=CC=C1COC(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 TWFAJNXORPXXHJ-UHFFFAOYSA-N 0.000 claims description 5
XPHBQOUOAVUTLL-UHFFFAOYSA-N (4,5-dimethoxy-2-nitrophenyl)methyl 4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]piperidine-1-carboxylate Chemical compound C1=C(OC)C(OC)=CC(COC(=O)N2CCC(CC2)C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)=C1[N+]([O-])=O XPHBQOUOAVUTLL-UHFFFAOYSA-N 0.000 claims description 5
JBVFHFGCUCLBAC-UHFFFAOYSA-N (4-nitrophenyl)methyl 4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]piperidine-1-carboxylate Chemical compound C1=CC([N+](=O)[O-])=CC=C1COC(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 JBVFHFGCUCLBAC-UHFFFAOYSA-N 0.000 claims description 5
BDCDBMMOQZVEQQ-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-cyclopropylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylic acid Chemical compound C1CC(C(=O)O)(CC2)CCC12C(NC=1C=2C=C3OCOC3=CC=2)=NC=1C(N=1)=CC=CC=1C1CC1 BDCDBMMOQZVEQQ-UHFFFAOYSA-N 0.000 claims description 5
PSFNVZCUNRDLSM-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n,n-diethylbicyclo[2.2.2]octane-4-carboxamide Chemical compound C1CC(C(=O)N(CC)CC)(CC2)CCC12C(N1)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CC(C)=N1 PSFNVZCUNRDLSM-UHFFFAOYSA-N 0.000 claims description 5
TYKPSDLNBWREBQ-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n,n-dimethylbicyclo[2.2.2]octane-4-carboxamide Chemical compound C1CC(C(=O)N(C)C)(CC2)CCC12C(N1)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CC(C)=N1 TYKPSDLNBWREBQ-UHFFFAOYSA-N 0.000 claims description 5
AVBSRIGBTOAPCC-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n,n-dipropylbicyclo[2.2.2]octane-4-carboxamide Chemical compound C1CC(C(=O)N(CCC)CCC)(CC2)CCC12C(N1)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CC(C)=N1 AVBSRIGBTOAPCC-UHFFFAOYSA-N 0.000 claims description 5
SCLUKIYIEQXKPC-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-(1,3-benzothiazol-2-yl)bicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(=O)NC=2SC3=CC=CC=C3N=2)C=2C=C3OCOC3=CC=2)=N1 SCLUKIYIEQXKPC-UHFFFAOYSA-N 0.000 claims description 5
WQGFGKHYEZFVEL-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-(1-hydroxy-1-phenylpropan-2-yl)bicyclo[2.2.2]octane-4-carboxamide Chemical compound C=1C=CC=CC=1C(O)C(C)NC(=O)C(CC1)(CC2)CCC12C(N1)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CC(C)=N1 WQGFGKHYEZFVEL-UHFFFAOYSA-N 0.000 claims description 5
OYLSBWOMVFQWKV-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-(1-methyl-5-methylsulfanyl-1,2,4-triazol-3-yl)bicyclo[2.2.2]octane-4-carboxamide Chemical compound CN1C(SC)=NC(NC(=O)C23CCC(CC2)(CC3)C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=C(C)C=CC=2)=N1 OYLSBWOMVFQWKV-UHFFFAOYSA-N 0.000 claims description 5
YKNSIFNFRJZJNZ-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-(5,7-difluoro-1,3-benzothiazol-2-yl)bicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(=O)NC=2SC3=C(F)C=C(F)C=C3N=2)C=2C=C3OCOC3=CC=2)=N1 YKNSIFNFRJZJNZ-UHFFFAOYSA-N 0.000 claims description 5
ZNHHQIKDYUGVDY-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-(pyridin-2-ylmethyl)bicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(=O)NCC=2N=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 ZNHHQIKDYUGVDY-UHFFFAOYSA-N 0.000 claims description 5
IDMSXJAGKSMKAQ-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-(pyridin-4-ylmethyl)bicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(=O)NCC=2C=CN=CC=2)C=2C=C3OCOC3=CC=2)=N1 IDMSXJAGKSMKAQ-UHFFFAOYSA-N 0.000 claims description 5
ZUTIQUZCDSCVSY-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-benzylbicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(=O)NCC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 ZUTIQUZCDSCVSY-UHFFFAOYSA-N 0.000 claims description 5
OLKOQFCACIBBJG-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-hydroxybicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(NC(=N2)C23CCC(CC2)(CC3)C(=O)NO)C=2C=C3OCOC3=CC=2)=N1 OLKOQFCACIBBJG-UHFFFAOYSA-N 0.000 claims description 5
RFHKQZKAHKOHRP-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-methoxybicyclo[2.2.2]octane-4-carboxamide Chemical compound C1CC(C(=O)NOC)(CC2)CCC12C(NC=1C=2C=C3OCOC3=CC=2)=NC=1C1=CC=CC(C)=N1 RFHKQZKAHKOHRP-UHFFFAOYSA-N 0.000 claims description 5
SCJDMLODCHYEER-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-methylsulfonylbicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(=O)NS(C)(=O)=O)C=2C=C3OCOC3=CC=2)=N1 SCJDMLODCHYEER-UHFFFAOYSA-N 0.000 claims description 5
DKSAUIAQFZUDED-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octan-4-amine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(N)(CC2)CC3)C=2C=C3OCOC3=CC=2)=N1 DKSAUIAQFZUDED-UHFFFAOYSA-N 0.000 claims description 5
XDONAADVYDVOCU-UHFFFAOYSA-N 1-[4-(3-methyl-4-oxoquinazolin-6-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylic acid Chemical compound CC1=CC=CC(C2=C(NC(=N2)C23CCC(CC2)(CC3)C(O)=O)C=2C=C3C(=O)N(C)C=NC3=CC=2)=N1 XDONAADVYDVOCU-UHFFFAOYSA-N 0.000 claims description 5
KXENDECZPMIZLE-UHFFFAOYSA-N 1-[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]piperidin-1-yl]-3-phenylpropan-1-one Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)C(=O)CCC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 KXENDECZPMIZLE-UHFFFAOYSA-N 0.000 claims description 5
SPIRDUBGWMKCEE-UHFFFAOYSA-N 1-[4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCC1C1=NC(C=2C=C3OCOC3=CC=2)=C(C=2N=CC=CC=2)N1 SPIRDUBGWMKCEE-UHFFFAOYSA-N 0.000 claims description 5
QNTZUABGHJBFPJ-UHFFFAOYSA-N 1-[4-[4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]piperidin-1-yl]sulfonylphenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 QNTZUABGHJBFPJ-UHFFFAOYSA-N 0.000 claims description 5
REYSLEGAAKFCRQ-UHFFFAOYSA-N 1-[5-(2-aminopyrimidin-4-yl)-4-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylic acid Chemical compound CC1=CC=CC(C2=C(NC(=N2)C23CCC(CC2)(CC3)C(O)=O)C=2N=C(N)N=CC=2)=N1 REYSLEGAAKFCRQ-UHFFFAOYSA-N 0.000 claims description 5
DCSXVNBJFYIXIH-UHFFFAOYSA-N 1-[5-(2-methylpyrimidin-4-yl)-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=NC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(N)=O)C2=CN3N=CN=C3C=C2)=N1 DCSXVNBJFYIXIH-UHFFFAOYSA-N 0.000 claims description 5
GDAIFEPYRASGRM-UHFFFAOYSA-N 1-[5-(2-methylpyrimidin-4-yl)-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylic acid Chemical compound CC1=NC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(O)=O)C2=CN3N=CN=C3C=C2)=N1 GDAIFEPYRASGRM-UHFFFAOYSA-N 0.000 claims description 5
KIZAXJYFDWLRFS-UHFFFAOYSA-N 1-[5-(2-methylpyrimidin-4-yl)-4-([1,2,4]triazolo[4,3-a]pyridin-6-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octan-4-ol Chemical compound CC1=NC=CC(C2=C(N=C(N2)C23CCC(O)(CC2)CC3)C2=CN3C=NN=C3C=C2)=N1 KIZAXJYFDWLRFS-UHFFFAOYSA-N 0.000 claims description 5
SQYJKVGOSYWORT-UHFFFAOYSA-N 1-[5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-2,3-dihydroindol-1-yl]ethanone Chemical compound C=1C=C2N(C(=O)C)CCC2=CC=1C1=CNN=C1C1=CC=CC=N1 SQYJKVGOSYWORT-UHFFFAOYSA-N 0.000 claims description 5
YGHSVVBPXIXHSF-UHFFFAOYSA-N 1-[5-(6-cyclopropylpyridin-2-yl)-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1h-imidazol-2-yl]-n-hydroxybicyclo[2.2.2]octane-4-carboxamide Chemical compound C1CC(C(=O)NO)(CC2)CCC12C(NC=1C2=CN3N=CN=C3C=C2)=NC=1C(N=1)=CC=CC=1C1CC1 YGHSVVBPXIXHSF-UHFFFAOYSA-N 0.000 claims description 5
NVJLNUFBDYBWQY-UHFFFAOYSA-N 1-[5-(6-cyclopropylpyridin-2-yl)-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylic acid Chemical compound C1CC(C(=O)O)(CC2)CCC12C(NC=1C2=CN3N=CN=C3C=C2)=NC=1C(N=1)=CC=CC=1C1CC1 NVJLNUFBDYBWQY-UHFFFAOYSA-N 0.000 claims description 5
YIBGSDUTNZLXET-UHFFFAOYSA-N 1-[5-(6-methylpyridin-2-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylic acid Chemical compound CC1=CC=CC(C2=C(NC(=N2)C23CCC(CC2)(CC3)C(O)=O)C=2C=C3N=CC=NC3=CC=2)=N1 YIBGSDUTNZLXET-UHFFFAOYSA-N 0.000 claims description 5
GWJQEWCTGGIYQC-UHFFFAOYSA-N 1-[5-[2-(cyclopropylamino)pyrimidin-4-yl]-4-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylic acid Chemical compound CC1=CC=CC(C2=C(NC(=N2)C23CCC(CC2)(CC3)C(O)=O)C=2N=C(NC3CC3)N=CC=2)=N1 GWJQEWCTGGIYQC-UHFFFAOYSA-N 0.000 claims description 5
PLFVJNCDYWCWML-UHFFFAOYSA-N 1-[6-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]pyridin-2-yl]ethanol Chemical compound CC(O)C1=CC=CC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=N1 PLFVJNCDYWCWML-UHFFFAOYSA-N 0.000 claims description 5
XYMWHITVFQOZSE-UHFFFAOYSA-N 1-methoxy-4-(5-pyridin-2-yl-1h-pyrazol-4-yl)isoquinoline Chemical compound C12=CC=CC=C2C(OC)=NC=C1C1=CNN=C1C1=CC=CC=N1 XYMWHITVFQOZSE-UHFFFAOYSA-N 0.000 claims description 5
SFZYRCUDHYKJJC-UHFFFAOYSA-N 1-tert-butyl-3-[6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazolin-4-yl]urea Chemical compound C1=C2C(NC(=O)NC(C)(C)C)=NC=NC2=CC=C1C1=CNN=C1C1=CC=CC=N1 SFZYRCUDHYKJJC-UHFFFAOYSA-N 0.000 claims description 5
LRKYHEWFSVQJMQ-UHFFFAOYSA-N 2,3-dimethyl-6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazolin-4-one Chemical compound C1=C2C(=O)N(C)C(C)=NC2=CC=C1C1=CNN=C1C1=CC=CC=N1 LRKYHEWFSVQJMQ-UHFFFAOYSA-N 0.000 claims description 5
MFNRPQVYVRQKII-UHFFFAOYSA-N 2,4-dimethoxy-5-(5-pyridin-2-yl-1h-pyrazol-4-yl)pyrimidine Chemical compound COC1=NC(OC)=NC=C1C1=C(C=2N=CC=CC=2)NN=C1 MFNRPQVYVRQKII-UHFFFAOYSA-N 0.000 claims description 5
QFVDOHIBLYRLPY-UHFFFAOYSA-N 2-(2,7-difluoro-3-hydroxy-6-oxoxanthen-9-yl)-5-[4-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]butylcarbamoyl]benzoic acid Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCCNC(=O)C=3C=C(C(=CC=3)C3=C4C=C(F)C(=O)C=C4OC4=CC(O)=C(F)C=C43)C(O)=O)N=CC=2)=N1 QFVDOHIBLYRLPY-UHFFFAOYSA-N 0.000 claims description 5
MCMKSMNPHIBOLT-UHFFFAOYSA-N 2-(3-methoxyphenyl)-n-[2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl]acetamide Chemical compound COC1=CC=CC(CC(=O)NC2=NC3=NC(=C(N3C=C2)C=2N=C(N=CC=2)S(C)(=O)=O)C=2N=C(C)C=CC=2)=C1 MCMKSMNPHIBOLT-UHFFFAOYSA-N 0.000 claims description 5
BUVRVVBYIQDIDT-UHFFFAOYSA-N 2-(3-pyridin-2-yl-4-quinolin-4-ylpyrazol-1-yl)ethanamine Chemical compound N=1N(CCN)C=C(C=2C3=CC=CC=C3N=CC=2)C=1C1=CC=CC=N1 BUVRVVBYIQDIDT-UHFFFAOYSA-N 0.000 claims description 5
FLMHPOCIZIPARJ-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CSC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 FLMHPOCIZIPARJ-UHFFFAOYSA-N 0.000 claims description 5
VYFQAELHCIQANB-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound CSC1=NC=CC(C=2N3C=CC(N)=NC3=NC=2C=2N=C(C)C=CC=2)=N1 VYFQAELHCIQANB-UHFFFAOYSA-N 0.000 claims description 5
DRUPRNRFTAHFGT-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)S(C)(=O)=O)=N1 DRUPRNRFTAHFGT-UHFFFAOYSA-N 0.000 claims description 5
DOGVCZGYQZYXAP-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C#N)C=2N=C(N=CC=2)S(C)(=O)=O)=N1 DOGVCZGYQZYXAP-UHFFFAOYSA-N 0.000 claims description 5
QBVDQHQMPZYGCP-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-(2-piperidin-1-ylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)N2CCCCC2)=N1 QBVDQHQMPZYGCP-UHFFFAOYSA-N 0.000 claims description 5
IYTJQGUUWQZKMH-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-[2-(2h-tetrazol-5-yl)pyrimidin-4-yl]imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)C=2NN=NN=2)=N1 IYTJQGUUWQZKMH-UHFFFAOYSA-N 0.000 claims description 5
WVAVXRCQIICYRN-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-pyrimidin-4-ylimidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=CN=CC=2)=N1 WVAVXRCQIICYRN-UHFFFAOYSA-N 0.000 claims description 5
TVCVBBJSTVIFLY-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-pyrimidin-4-ylimidazo[1,2-a]pyrimidin-7-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC(N)=NC3=N2)C=2N=CN=CC=2)=N1 TVCVBBJSTVIFLY-UHFFFAOYSA-N 0.000 claims description 5
AEUAOIYYRAMAQD-UHFFFAOYSA-N 2-[2-(1-benzylsulfonylpiperidin-4-yl)-4-(2-fluoropyridin-4-yl)-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)CC=2C=CC=CC=2)C=2C=C(F)N=CC=2)=N1 AEUAOIYYRAMAQD-UHFFFAOYSA-N 0.000 claims description 5
ISXNRDZPHJMGIT-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]-6-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=CC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=N1 ISXNRDZPHJMGIT-UHFFFAOYSA-N 0.000 claims description 5
WPTMLMRCXDJZNI-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]-6-cyclopropylpyridine Chemical compound C1CC1C1=CC=CC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=N1 WPTMLMRCXDJZNI-UHFFFAOYSA-N 0.000 claims description 5
VQNGFTSKHNQZEI-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]-6-ethenylpyridine Chemical compound C=CC1=CC=CC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=N1 VQNGFTSKHNQZEI-UHFFFAOYSA-N 0.000 claims description 5
BJYFDVHHZLGZSW-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]-6-ethylpyridine Chemical compound CCC1=CC=CC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=N1 BJYFDVHHZLGZSW-UHFFFAOYSA-N 0.000 claims description 5
XPJQTAGLWLONLB-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]-6-prop-1-enylpyridine Chemical compound CC=CC1=CC=CC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=N1 XPJQTAGLWLONLB-UHFFFAOYSA-N 0.000 claims description 5
VZQJKFWHVVOZGS-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]-6-propan-2-ylpyridine Chemical compound CC(C)C1=CC=CC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=N1 VZQJKFWHVVOZGS-UHFFFAOYSA-N 0.000 claims description 5
DDLCKXIXNHICNI-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]-6-propylpyridine Chemical compound CCCC1=CC=CC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=N1 DDLCKXIXNHICNI-UHFFFAOYSA-N 0.000 claims description 5
YHDUMDBRUMICHF-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-benzylsulfonylpiperidin-3-yl)-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CN(CCC2)S(=O)(=O)CC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 YHDUMDBRUMICHF-UHFFFAOYSA-N 0.000 claims description 5
KFRZBSUJGFDECR-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-benzylsulfonylpiperidin-4-yl)-1h-imidazol-5-yl]-6-bromopyridine Chemical compound BrC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)CC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 KFRZBSUJGFDECR-UHFFFAOYSA-N 0.000 claims description 5
YUOCFEKWIWPITK-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-benzylsulfonylpiperidin-4-yl)-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)CC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 YUOCFEKWIWPITK-UHFFFAOYSA-N 0.000 claims description 5
SGQKTIWTZZVBHS-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-benzylsulfonylpyrrolidin-3-yl)-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CN(CC2)S(=O)(=O)CC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 SGQKTIWTZZVBHS-UHFFFAOYSA-N 0.000 claims description 5
GUTRQDMDMYZGES-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-butylsulfonylpiperidin-3-yl)-1h-imidazol-5-yl]-6-methylpyridine Chemical compound C1N(S(=O)(=O)CCCC)CCCC1C1=NC(C=2C=C3OCOC3=CC=2)=C(C=2N=C(C)C=CC=2)N1 GUTRQDMDMYZGES-UHFFFAOYSA-N 0.000 claims description 5
HQNAVRIDVCVQQZ-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-butylsulfonylpiperidin-4-yl)-1h-imidazol-5-yl]-6-methylpyridine Chemical compound C1CN(S(=O)(=O)CCCC)CCC1C1=NC(C=2C=C3OCOC3=CC=2)=C(C=2N=C(C)C=CC=2)N1 HQNAVRIDVCVQQZ-UHFFFAOYSA-N 0.000 claims description 5
IEMNRBMFCIUNGS-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-butylsulfonylpiperidin-4-yl)-1h-imidazol-5-yl]pyridine Chemical compound C1CN(S(=O)(=O)CCCC)CCC1C1=NC(C=2C=C3OCOC3=CC=2)=C(C=2N=CC=CC=2)N1 IEMNRBMFCIUNGS-UHFFFAOYSA-N 0.000 claims description 5
CWPONJIVPGFGOA-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-butylsulfonylpyrrolidin-3-yl)-1h-imidazol-5-yl]-6-methylpyridine Chemical compound C1N(S(=O)(=O)CCCC)CCC1C1=NC(C=2C=C3OCOC3=CC=2)=C(C=2N=C(C)C=CC=2)N1 CWPONJIVPGFGOA-UHFFFAOYSA-N 0.000 claims description 5
ADEUXTLXWVFLME-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-ethylsulfonylpiperidin-4-yl)-1h-imidazol-5-yl]-6-methylpyridine Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=NC(C=2C=C3OCOC3=CC=2)=C(C=2N=C(C)C=CC=2)N1 ADEUXTLXWVFLME-UHFFFAOYSA-N 0.000 claims description 5
WKHVJQNTICLHHP-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-ethylsulfonylpiperidin-4-yl)-1h-imidazol-5-yl]pyridine Chemical compound C1CN(S(=O)(=O)CC)CCC1C1=NC(C=2C=C3OCOC3=CC=2)=C(C=2N=CC=CC=2)N1 WKHVJQNTICLHHP-UHFFFAOYSA-N 0.000 claims description 5
SNYRGCFIRFHTBD-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-methylsulfonylpiperidin-4-yl)-1h-imidazol-5-yl]pyridine Chemical compound C1CN(S(=O)(=O)C)CCC1C1=NC(C=2C=C3OCOC3=CC=2)=C(C=2N=CC=CC=2)N1 SNYRGCFIRFHTBD-UHFFFAOYSA-N 0.000 claims description 5
BXUBKWMJQNIVNK-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-methylsulfonylpyrrolidin-3-yl)-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CN(CC2)S(C)(=O)=O)C=2C=C3OCOC3=CC=2)=N1 BXUBKWMJQNIVNK-UHFFFAOYSA-N 0.000 claims description 5
DXBVGXRVODZVNR-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-propan-2-ylsulfonylpiperidin-4-yl)-1h-imidazol-5-yl]-6-methylpyridine Chemical compound C1CN(S(=O)(=O)C(C)C)CCC1C1=NC(C=2C=C3OCOC3=CC=2)=C(C=2N=C(C)C=CC=2)N1 DXBVGXRVODZVNR-UHFFFAOYSA-N 0.000 claims description 5
YBQSOTUUSVQSDX-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-propan-2-ylsulfonylpiperidin-4-yl)-1h-imidazol-5-yl]pyridine Chemical compound C1CN(S(=O)(=O)C(C)C)CCC1C1=NC(C=2C=C3OCOC3=CC=2)=C(C=2N=CC=CC=2)N1 YBQSOTUUSVQSDX-UHFFFAOYSA-N 0.000 claims description 5
WFAFZVJXDCKORT-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-propylsulfonylpiperidin-4-yl)-1h-imidazol-5-yl]-6-methylpyridine Chemical compound C1CN(S(=O)(=O)CCC)CCC1C1=NC(C=2C=C3OCOC3=CC=2)=C(C=2N=C(C)C=CC=2)N1 WFAFZVJXDCKORT-UHFFFAOYSA-N 0.000 claims description 5
AQCMMAOQMOKPJQ-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-thiophen-2-ylsulfonylpiperidin-4-yl)-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)C=2SC=CC=2)C=2C=C3OCOC3=CC=2)=N1 AQCMMAOQMOKPJQ-UHFFFAOYSA-N 0.000 claims description 5
PBXFIFABKLKBKE-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-thiophen-3-ylsulfonylpiperidin-4-yl)-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)C2=CSC=C2)C=2C=C3OCOC3=CC=2)=N1 PBXFIFABKLKBKE-UHFFFAOYSA-N 0.000 claims description 5
JWWQUDKZMQCNNI-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(1-methylimidazol-4-yl)sulfonylpyrrolidin-3-yl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CN(CC2)S(=O)(=O)C=2N=CN(C)C=2)C=2C=C3OCOC3=CC=2)=N1 JWWQUDKZMQCNNI-UHFFFAOYSA-N 0.000 claims description 5
WIESZJDBWQBFCO-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(2-naphthalen-1-ylethylsulfonyl)piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C=1C=CC2=CC=CC=C2C=1CCS(=O)(=O)N(CC1)CCC1C(N1)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CC=N1 WIESZJDBWQBFCO-UHFFFAOYSA-N 0.000 claims description 5
CHISAJWFSHSAGP-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(2-naphthalen-2-ylethylsulfonyl)piperidin-4-yl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)CCC=2C=C3C=CC=CC3=CC=2)C=2C=C3OCOC3=CC=2)=N1 CHISAJWFSHSAGP-UHFFFAOYSA-N 0.000 claims description 5
NIVOFZWVKLYSMZ-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(2-phenylethenylsulfonyl)piperidin-4-yl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)C=CC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 NIVOFZWVKLYSMZ-UHFFFAOYSA-N 0.000 claims description 5
HLLZYGDCAIEDSD-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(2-phenylethenylsulfonyl)piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C1CC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CCN1S(=O)(=O)C=CC1=CC=CC=C1 HLLZYGDCAIEDSD-UHFFFAOYSA-N 0.000 claims description 5
DKBOGMRTFOKIEM-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(2-phenylethylsulfonyl)piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C1CC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CCN1S(=O)(=O)CCC1=CC=CC=C1 DKBOGMRTFOKIEM-UHFFFAOYSA-N 0.000 claims description 5
ZTIDOCNVLREPJM-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(3,4-dichlorophenyl)sulfonylpiperidin-4-yl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)C=2C=C(Cl)C(Cl)=CC=2)C=2C=C3OCOC3=CC=2)=N1 ZTIDOCNVLREPJM-UHFFFAOYSA-N 0.000 claims description 5
UYMPGKGTHHSJND-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(3,4-dichlorophenyl)sulfonylpiperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 UYMPGKGTHHSJND-UHFFFAOYSA-N 0.000 claims description 5
FJTQBZQIVAMWKJ-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(4-chlorophenyl)sulfonylpiperidin-4-yl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)C=2C=CC(Cl)=CC=2)C=2C=C3OCOC3=CC=2)=N1 FJTQBZQIVAMWKJ-UHFFFAOYSA-N 0.000 claims description 5
DDWDJRWPMOQIFD-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(4-chlorophenyl)sulfonylpiperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 DDWDJRWPMOQIFD-UHFFFAOYSA-N 0.000 claims description 5
WQRSAMRRRMOASD-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(4-chlorophenyl)sulfonylpyrrolidin-3-yl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CN(CC2)S(=O)(=O)C=2C=CC(Cl)=CC=2)C=2C=C3OCOC3=CC=2)=N1 WQRSAMRRRMOASD-UHFFFAOYSA-N 0.000 claims description 5
MPODDBWOVRLHKU-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(4-methoxyphenyl)sulfonylpiperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 MPODDBWOVRLHKU-UHFFFAOYSA-N 0.000 claims description 5
IZSKNMHGLYPANF-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(4-methylphenyl)sulfonylpiperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 IZSKNMHGLYPANF-UHFFFAOYSA-N 0.000 claims description 5
DUFDYJBGCYXACR-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(4-phenoxyphenyl)sulfonylpiperidin-4-yl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)C=2C=CC(OC=3C=CC=CC=3)=CC=2)C=2C=C3OCOC3=CC=2)=N1 DUFDYJBGCYXACR-UHFFFAOYSA-N 0.000 claims description 5
JMKJVYXTWYNLEK-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(4-phenylphenyl)sulfonylpiperidin-4-yl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 JMKJVYXTWYNLEK-UHFFFAOYSA-N 0.000 claims description 5
QNWJZGWOVACKLE-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(cyclohexylmethyl)piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C1CC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CCN1CC1CCCCC1 QNWJZGWOVACKLE-UHFFFAOYSA-N 0.000 claims description 5
FZEZTGKNVDQBCE-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(pyridin-2-ylmethylsulfonyl)piperidin-4-yl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)CC=2N=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 FZEZTGKNVDQBCE-UHFFFAOYSA-N 0.000 claims description 5
SATHLSRFOICFMQ-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(pyridin-3-ylmethylsulfonyl)piperidin-4-yl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)CC=2C=NC=CC=2)C=2C=C3OCOC3=CC=2)=N1 SATHLSRFOICFMQ-UHFFFAOYSA-N 0.000 claims description 5
WSMSMYWLCAAAKS-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound O1C(C)(C)OCC1CN1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 WSMSMYWLCAAAKS-UHFFFAOYSA-N 0.000 claims description 5
BSACKBHLZQSGCB-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-[(2-nitrophenyl)methylsulfonyl]piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound [O-][N+](=O)C1=CC=CC=C1CS(=O)(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 BSACKBHLZQSGCB-UHFFFAOYSA-N 0.000 claims description 5
XHVXAVMCXRSSIJ-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-[(3,4-dichlorophenyl)methylsulfonyl]piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C1=C(Cl)C(Cl)=CC=C1CS(=O)(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 XHVXAVMCXRSSIJ-UHFFFAOYSA-N 0.000 claims description 5
MPSCSDJNRHTYAK-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-[(3,5-dichlorophenyl)methylsulfonyl]piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound ClC1=CC(Cl)=CC(CS(=O)(=O)N2CCC(CC2)C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)=C1 MPSCSDJNRHTYAK-UHFFFAOYSA-N 0.000 claims description 5
VEDFSRDPRBIAHR-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-[(3,5-difluorophenyl)methylsulfonyl]piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound FC1=CC(F)=CC(CS(=O)(=O)N2CCC(CC2)C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)=C1 VEDFSRDPRBIAHR-UHFFFAOYSA-N 0.000 claims description 5
DAQSRPVCLQSDTE-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-[(4-chlorophenyl)methylsulfonyl]piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C1=CC(Cl)=CC=C1CS(=O)(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 DAQSRPVCLQSDTE-UHFFFAOYSA-N 0.000 claims description 5
QPDBYYHHNUCVME-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-[(4-methylphenyl)methyl]piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C1=CC(C)=CC=C1CN1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 QPDBYYHHNUCVME-UHFFFAOYSA-N 0.000 claims description 5
OGRVREHRYLXFIJ-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-[[3,5-bis(trifluoromethyl)phenyl]methylsulfonyl]piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(CS(=O)(=O)N2CCC(CC2)C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)=C1 OGRVREHRYLXFIJ-UHFFFAOYSA-N 0.000 claims description 5
VCZVKWZFYAUTMB-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-[[3-(trifluoromethyl)phenyl]methylsulfonyl]piperidin-4-yl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)CC=2C=C(C=CC=2)C(F)(F)F)C=2C=C3OCOC3=CC=2)=N1 VCZVKWZFYAUTMB-UHFFFAOYSA-N 0.000 claims description 5
QOLBRKVCDJBHLM-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-[[3-fluoro-5-(trifluoromethyl)phenyl]methyl]piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound FC(F)(F)C1=CC(F)=CC(CN2CCC(CC2)C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)=C1 QOLBRKVCDJBHLM-UHFFFAOYSA-N 0.000 claims description 5
KPXYXCVXSFYBBO-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-[[4-(trifluoromethyl)phenyl]methylsulfonyl]piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C1=CC(C(F)(F)F)=CC=C1CS(=O)(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 KPXYXCVXSFYBBO-UHFFFAOYSA-N 0.000 claims description 5
KLGKGHCBTZTAGG-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[4-(sulfamoylamino)-1-bicyclo[2.2.2]octanyl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)NS(N)(=O)=O)C=2C=C3OCOC3=CC=2)=N1 KLGKGHCBTZTAGG-UHFFFAOYSA-N 0.000 claims description 5
KHDKNUGNYWMNRU-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-piperidin-4-yl-1h-imidazol-5-yl]pyridine Chemical compound C1=C2OCOC2=CC=C1C=1N=C(C2CCNCC2)NC=1C1=CC=CC=N1 KHDKNUGNYWMNRU-UHFFFAOYSA-N 0.000 claims description 5
OUISUIBLHNSWMA-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-3-(6-methylpyridin-2-yl)pyrazol-1-yl]acetonitrile Chemical compound CC1=CC=CC(C=2C(=CN(CC#N)N=2)C=2C=C3OCOC3=CC=2)=N1 OUISUIBLHNSWMA-UHFFFAOYSA-N 0.000 claims description 5
GEGAGIPGIGCNRW-UHFFFAOYSA-N 2-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)-1h-pyrazol-5-yl]pyridine Chemical compound C=1C=C2OCCOC2=CC=1C1=CNN=C1C1=CC=CC=N1 GEGAGIPGIGCNRW-UHFFFAOYSA-N 0.000 claims description 5
OBKNPOIEIDWLFN-UHFFFAOYSA-N 2-[4-(2,3-dihydro-1-benzofuran-5-yl)-1h-pyrazol-5-yl]pyridine Chemical compound C=1C=C2OCCC2=CC=1C1=CNN=C1C1=CC=CC=N1 OBKNPOIEIDWLFN-UHFFFAOYSA-N 0.000 claims description 5
HTLSOALCDIEOBI-UHFFFAOYSA-N 2-[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-1-bicyclo[2.2.2]octanyl]acetic acid Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC(O)=O)(CC2)CC3)C=2C=C3OCOC3=CC=2)=N1 HTLSOALCDIEOBI-UHFFFAOYSA-N 0.000 claims description 5
WTMCRVJVKGKDOO-UHFFFAOYSA-N 2-[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-1-bicyclo[2.2.2]octanyl]acetonitrile Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC#N)(CC2)CC3)C=2C=C3OCOC3=CC=2)=N1 WTMCRVJVKGKDOO-UHFFFAOYSA-N 0.000 claims description 5
FVJFPPZGRCXFRL-UHFFFAOYSA-N 2-[[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]piperidin-1-yl]sulfonylmethyl]aniline Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)CC=2C(=CC=CC=2)N)C=2C=C3OCOC3=CC=2)=N1 FVJFPPZGRCXFRL-UHFFFAOYSA-N 0.000 claims description 5
IHWIMLMSJKMBBR-UHFFFAOYSA-N 2-methyl-4-methylsulfanyl-6-(5-pyridin-2-yl-1h-pyrazol-4-yl)pyrimidine Chemical compound CC1=NC(SC)=CC(C=2C(=NNC=2)C=2N=CC=CC=2)=N1 IHWIMLMSJKMBBR-UHFFFAOYSA-N 0.000 claims description 5
QGAGLWKUTXHKMN-UHFFFAOYSA-N 2-methyl-6-(5-pyridin-2-yl-1h-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyridine Chemical compound C=1N2N=C(C)N=C2C=CC=1C1=CNN=C1C1=CC=CC=N1 QGAGLWKUTXHKMN-UHFFFAOYSA-N 0.000 claims description 5
IDWPHPUVJLLXHG-UHFFFAOYSA-N 3,3-dimethyl-n-[2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl]butanamide Chemical compound CSC1=NC=CC(C=2N3C=CC(NC(=O)CC(C)(C)C)=NC3=NC=2C=2N=C(C)C=CC=2)=N1 IDWPHPUVJLLXHG-UHFFFAOYSA-N 0.000 claims description 5
SRUUQKVZNDNFFD-UHFFFAOYSA-N 3,3-dimethyl-n-[2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl]butanamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(NC(=O)CC(C)(C)C)=NC3=N2)C=2N=C(N=CC=2)S(C)(=O)=O)=N1 SRUUQKVZNDNFFD-UHFFFAOYSA-N 0.000 claims description 5
NQGDNOYOIMCELQ-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)-n-(2-oxo-2-pyridin-3-ylethyl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NCC(=O)C=2C=NC=CC=2)C=2N=C(N)N=CC=2)=N1 NQGDNOYOIMCELQ-UHFFFAOYSA-N 0.000 claims description 5
ZSGAZWNRAGROEO-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)-n-(piperidin-3-ylmethyl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NCC2CNCCC2)C=2N=C(N)N=CC=2)=N1 ZSGAZWNRAGROEO-UHFFFAOYSA-N 0.000 claims description 5
DYTLNCMKOFYAIP-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)-n-methylsulfonylimidazo[1,2-a]pyridine-6-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C(=O)NS(C)(=O)=O)C=2N=C(N)N=CC=2)=N1 DYTLNCMKOFYAIP-UHFFFAOYSA-N 0.000 claims description 5
PMPGOGWILLVGCS-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-8-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=C(N)C3=N2)C=2N=C(N)N=CC=2)=N1 PMPGOGWILLVGCS-UHFFFAOYSA-N 0.000 claims description 5
BAUQEWQBBHXUMG-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carbonitrile Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C#N)C=2N=C(N)N=CC=2)=N1 BAUQEWQBBHXUMG-UHFFFAOYSA-N 0.000 claims description 5
WBSWEUKONANKOY-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(N)=O)C=2N=C(N)N=CC=2)=N1 WBSWEUKONANKOY-UHFFFAOYSA-N 0.000 claims description 5
JJRWXPAUYRHWSS-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyrimidin-7-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC(N)=NC3=N2)C=2N=C(N)N=CC=2)=N1 JJRWXPAUYRHWSS-UHFFFAOYSA-N 0.000 claims description 5
DZYLDAACLSDXJN-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-6-methyl-2-(6-methylpyridin-2-yl)-n-(2-pyridin-4-ylethyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C12=NC(C=3N=C(C)C=CC=3)=C(C=3N=C(N)N=CC=3)N2C=C(C)C=C1NCCC1=CC=NC=C1 DZYLDAACLSDXJN-UHFFFAOYSA-N 0.000 claims description 5
VJJLFUGNAPGFAM-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-N-hydroxy-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C(=O)NO)C=2N=C(N)N=CC=2)=N1 VJJLFUGNAPGFAM-UHFFFAOYSA-N 0.000 claims description 5
DZASFVSKVJGYPH-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-N-hydroxy-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NO)C=2N=C(N)N=CC=2)=N1 DZASFVSKVJGYPH-UHFFFAOYSA-N 0.000 claims description 5
VKODDBPPNQPIEV-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n',n'-dimethyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carbohydrazide Chemical compound N1=C2C=C(C(=O)NN(C)C)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 VKODDBPPNQPIEV-UHFFFAOYSA-N 0.000 claims description 5
WOBVNDLMPGASJH-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-(2-methoxyethyl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NCCOC)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(N)=N1 WOBVNDLMPGASJH-UHFFFAOYSA-N 0.000 claims description 5
DSZXRZARDVKLEJ-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-[2-(dimethylamino)ethyl]-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound N1=C2C=C(C(=O)NCCN(C)C)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 DSZXRZARDVKLEJ-UHFFFAOYSA-N 0.000 claims description 5
HWDOSLVNGNQUSJ-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-cyclopropyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C(=O)NC2CC2)C=2N=C(N)N=CC=2)=N1 HWDOSLVNGNQUSJ-UHFFFAOYSA-N 0.000 claims description 5
KEVVIUGJRUOWCB-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-cyclopropyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NC2CC2)C=2N=C(N)N=CC=2)=N1 KEVVIUGJRUOWCB-UHFFFAOYSA-N 0.000 claims description 5
WNOGQPVYYPDYIN-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-ethyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NCC)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(N)=N1 WNOGQPVYYPDYIN-UHFFFAOYSA-N 0.000 claims description 5
PTALXKKEJWSJGX-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-ethyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound N1=C2C=C(C(=O)NCC)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 PTALXKKEJWSJGX-UHFFFAOYSA-N 0.000 claims description 5
RIHSPLOZUDDXSE-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-methoxy-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NOC)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(N)=N1 RIHSPLOZUDDXSE-UHFFFAOYSA-N 0.000 claims description 5
AMODHECBNXJGPF-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-methoxy-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound N1=C2C=C(C(=O)NOC)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 AMODHECBNXJGPF-UHFFFAOYSA-N 0.000 claims description 5
ZFGJPLYSVPCNAA-UHFFFAOYSA-N 3-(2-methylsulfanylpyrimidin-4-yl)-2-pyridin-2-ylimidazo[1,2-a]pyridine Chemical compound CSC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=CC=CC=2)=N1 ZFGJPLYSVPCNAA-UHFFFAOYSA-N 0.000 claims description 5
MIJYWKSDJJUTCG-UHFFFAOYSA-N 3-(3-methoxyphenyl)-5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-2,1-benzoxazole Chemical compound COC1=CC=CC(C2=C3C=C(C=CC3=NO2)C2=C(NN=C2)C=2N=CC=CC=2)=C1 MIJYWKSDJJUTCG-UHFFFAOYSA-N 0.000 claims description 5
PKYNGYYFDJWSPD-UHFFFAOYSA-N 3-(3-pyridin-2-yl-4-quinolin-4-ylpyrazol-1-yl)propan-1-amine Chemical compound N=1N(CCCN)C=C(C=2C3=CC=CC=C3N=CC=2)C=1C1=CC=CC=N1 PKYNGYYFDJWSPD-UHFFFAOYSA-N 0.000 claims description 5
GKMSJYFFCJBASE-UHFFFAOYSA-N 3-(3-pyridin-2-yl-4-quinolin-4-ylpyrazol-1-yl)propanoic acid Chemical compound N=1N(CCC(=O)O)C=C(C=2C3=CC=CC=C3N=CC=2)C=1C1=CC=CC=N1 GKMSJYFFCJBASE-UHFFFAOYSA-N 0.000 claims description 5
OVWQVJJJLDIODX-UHFFFAOYSA-N 3-(4-chlorophenyl)-5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-2,1-benzoxazole Chemical compound C1=CC(Cl)=CC=C1C1=C2C=C(C=3C(=NNC=3)C=3N=CC=CC=3)C=CC2=NO1 OVWQVJJJLDIODX-UHFFFAOYSA-N 0.000 claims description 5
JGJUOHQSJQGVKB-UHFFFAOYSA-N 3-(4-ethylphenyl)-5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-2,1-benzoxazole Chemical compound C1=CC(CC)=CC=C1C1=C2C=C(C=3C(=NNC=3)C=3N=CC=CC=3)C=CC2=NO1 JGJUOHQSJQGVKB-UHFFFAOYSA-N 0.000 claims description 5
VKVHXDKKGYMTPU-UHFFFAOYSA-N 3-(4-methoxyphenyl)-5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-2,1-benzoxazole Chemical compound C1=CC(OC)=CC=C1C1=C2C=C(C=3C(=NNC=3)C=3N=CC=CC=3)C=CC2=NO1 VKVHXDKKGYMTPU-UHFFFAOYSA-N 0.000 claims description 5
VCIAFTLLDVOKLY-UHFFFAOYSA-N 3-[(4-nitrophenyl)methyl]-6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazolin-4-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1CN1C(=O)C2=CC(C=3C(=NNC=3)C=3N=CC=CC=3)=CC=C2N=C1 VCIAFTLLDVOKLY-UHFFFAOYSA-N 0.000 claims description 5
CRXCBJUEAVHWOS-UHFFFAOYSA-N 3-[2-(2-methylaziridin-1-yl)pyrimidin-4-yl]-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine Chemical compound CC1CN1C1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 CRXCBJUEAVHWOS-UHFFFAOYSA-N 0.000 claims description 5
ITDLSWQHTALTPU-UHFFFAOYSA-N 3-[2-(azetidin-1-yl)pyrimidin-4-yl]-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)N2CCC2)=N1 ITDLSWQHTALTPU-UHFFFAOYSA-N 0.000 claims description 5
GYSJFFZLKJKITE-UHFFFAOYSA-N 3-[4-(1,3-benzodioxol-5-yl)-3-(6-methylpyridin-2-yl)pyrazol-1-yl]propanenitrile Chemical compound CC1=CC=CC(C=2C(=CN(CCC#N)N=2)C=2C=C3OCOC3=CC=2)=N1 GYSJFFZLKJKITE-UHFFFAOYSA-N 0.000 claims description 5
KWAPKVNILUFYMY-UHFFFAOYSA-N 3-methyl-6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazolin-4-one Chemical compound C1=C2C(=O)N(C)C=NC2=CC=C1C1=CNN=C1C1=CC=CC=N1 KWAPKVNILUFYMY-UHFFFAOYSA-N 0.000 claims description 5
YBHYZXZQTQWBQB-UHFFFAOYSA-N 3-methyl-6-[5-(6-methylpyridin-2-yl)-1h-pyrazol-4-yl]quinazolin-4-one Chemical compound CC1=CC=CC(C=2C(=CNN=2)C=2C=C3C(=O)N(C)C=NC3=CC=2)=N1 YBHYZXZQTQWBQB-UHFFFAOYSA-N 0.000 claims description 5
UDWZGKJGQUDLSG-UHFFFAOYSA-N 4-(2-pyridin-2-ylimidazo[1,2-a]pyridin-3-yl)-n-(pyridin-3-ylmethyl)pyrimidin-2-amine Chemical compound C=1C=CN=CC=1CNC(N=1)=NC=CC=1C(N1C=CC=CC1=N1)=C1C1=CC=CC=N1 UDWZGKJGQUDLSG-UHFFFAOYSA-N 0.000 claims description 5
IUXZYJGBRTUWHZ-UHFFFAOYSA-N 4-(2-pyridin-2-ylimidazo[1,2-a]pyridin-3-yl)pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=CC=CC=2)=N1 IUXZYJGBRTUWHZ-UHFFFAOYSA-N 0.000 claims description 5
OKLAIKUJFGYQNY-UHFFFAOYSA-N 4-(2-pyridin-2-ylpyrazolo[1,5-a]pyridin-3-yl)pyrimidin-2-amine Chemical compound NC1=NC=CC(C2=C3C=CC=CN3N=C2C=2N=CC=CC=2)=N1 OKLAIKUJFGYQNY-UHFFFAOYSA-N 0.000 claims description 5
LORWLLUMJKJESN-UHFFFAOYSA-N 4-(4-methoxyphenyl)-6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazoline Chemical compound C1=CC(OC)=CC=C1C1=NC=NC2=CC=C(C=3C(=NNC=3)C=3N=CC=CC=3)C=C12 LORWLLUMJKJESN-UHFFFAOYSA-N 0.000 claims description 5
XEQUMANZORSJSQ-UHFFFAOYSA-N 4-(5-pyridin-2-yl-1h-pyrazol-4-yl)-2h-isoquinolin-1-one Chemical compound C12=CC=CC=C2C(=O)NC=C1C1=CNN=C1C1=CC=CC=N1 XEQUMANZORSJSQ-UHFFFAOYSA-N 0.000 claims description 5
HJWAOCQEWUVDQM-UHFFFAOYSA-N 4-(5-pyridin-2-yl-1h-pyrazol-4-yl)-2h-phthalazin-1-one Chemical compound C12=CC=CC=C2C(=O)NN=C1C1=CNN=C1C1=CC=CC=N1 HJWAOCQEWUVDQM-UHFFFAOYSA-N 0.000 claims description 5
QTIQBUCPHAGXIX-UHFFFAOYSA-N 4-[2-(1-benzylsulfonylpiperidin-4-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]-n-[(4-methoxyphenyl)methyl]pyridin-2-amine Chemical compound C1=CC(OC)=CC=C1CNC1=CC(C2=C(NC(=N2)C2CCN(CC2)S(=O)(=O)CC=2C=CC=CC=2)C=2N=C(C)C=CC=2)=CC=N1 QTIQBUCPHAGXIX-UHFFFAOYSA-N 0.000 claims description 5
ZJRFSDKQGLOMFX-UHFFFAOYSA-N 4-[2-(1-butylsulfonylpiperidin-4-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-4-yl]pyridin-2-amine Chemical compound C1CN(S(=O)(=O)CCCC)CCC1C1=NC(C=2C=C(N)N=CC=2)=C(C=2N=C(C)C=CC=2)N1 ZJRFSDKQGLOMFX-UHFFFAOYSA-N 0.000 claims description 5
YBHWFXBSFOTTDF-UHFFFAOYSA-N 4-[2-(6-chloropyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(Cl)C=CC=2)=N1 YBHWFXBSFOTTDF-UHFFFAOYSA-N 0.000 claims description 5
UCEORFVRGDPMJZ-UHFFFAOYSA-N 4-[2-(6-chloropyridin-2-yl)pyrazolo[1,5-c]pyrimidin-3-yl]pyrimidin-2-amine Chemical compound NC1=NC=CC(C2=C3C=CN=CN3N=C2C=2N=C(Cl)C=CC=2)=N1 UCEORFVRGDPMJZ-UHFFFAOYSA-N 0.000 claims description 5
ZIKNHXBNMFKMFV-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(2-morpholin-4-ylethyl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCN3CCOCC3)N=CC=2)=N1 ZIKNHXBNMFKMFV-UHFFFAOYSA-N 0.000 claims description 5
UMUBGGWVFYWKPC-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(2-pyridin-2-ylethyl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCC=3N=CC=CC=3)N=CC=2)=N1 UMUBGGWVFYWKPC-UHFFFAOYSA-N 0.000 claims description 5
XRHDZRZVBYMLHG-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(2-pyridin-3-ylethyl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCC=3C=NC=CC=3)N=CC=2)=N1 XRHDZRZVBYMLHG-UHFFFAOYSA-N 0.000 claims description 5
PGEFNWQUJQHPLE-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(2-pyridin-4-ylethyl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCC=3C=CN=CC=3)N=CC=2)=N1 PGEFNWQUJQHPLE-UHFFFAOYSA-N 0.000 claims description 5
WNHKNNXDZWKEPX-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(2h-tetrazol-5-yl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NC=3NN=NN=3)N=CC=2)=N1 WNHKNNXDZWKEPX-UHFFFAOYSA-N 0.000 claims description 5
OXNVLQQCADIKLE-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(3-morpholin-4-ylpropyl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCN3CCOCC3)N=CC=2)=N1 OXNVLQQCADIKLE-UHFFFAOYSA-N 0.000 claims description 5
DKWLODKAWHEALD-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(3-piperidin-1-ylpropyl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCN3CCCCC3)N=CC=2)=N1 DKWLODKAWHEALD-UHFFFAOYSA-N 0.000 claims description 5
VHVLKQPXJUKJFV-GOSISDBHSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-[(1r)-1-phenylethyl]pyrimidin-2-amine Chemical compound N([C@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1C(N1C=CC=CC1=N1)=C1C1=CC=CC(C)=N1 VHVLKQPXJUKJFV-GOSISDBHSA-N 0.000 claims description 5
GLWTXYIDCICEOP-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-propan-2-ylpyrimidin-2-amine Chemical compound CC(C)NC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 GLWTXYIDCICEOP-UHFFFAOYSA-N 0.000 claims description 5
UDPIROHVSULNKG-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N)N=CC=2)=N1 UDPIROHVSULNKG-UHFFFAOYSA-N 0.000 claims description 5
AMZCVYMZEGXAJP-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidine-2-carbonitrile Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)C#N)=N1 AMZCVYMZEGXAJP-UHFFFAOYSA-N 0.000 claims description 5
PUMALOKTAVGLKL-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidine-2-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)C(N)=O)=N1 PUMALOKTAVGLKL-UHFFFAOYSA-N 0.000 claims description 5
QMGFXZTTZWZHID-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)pyrazolo[1,5-a]pyrazin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C=2C(=C3C=NC=CN3N=2)C=2N=C(N)N=CC=2)=N1 QMGFXZTTZWZHID-UHFFFAOYSA-N 0.000 claims description 5
FSMFIPLMGNQWQW-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)pyrazolo[1,5-a]pyrimidin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C=2C(=C3N=CC=CN3N=2)C=2N=C(N)N=CC=2)=N1 FSMFIPLMGNQWQW-UHFFFAOYSA-N 0.000 claims description 5
MHSGTSAQVXECLK-UHFFFAOYSA-N 4-[2-[2-[4-(1,3-benzodioxol-5-yl)-3-(6-methylpyridin-2-yl)pyrazol-1-yl]ethoxy]ethoxy]bicyclo[2.2.2]octane-1-carboxylic acid Chemical compound CC1=CC=CC(C=2C(=CN(CCOCCOC34CCC(CC3)(CC4)C(O)=O)N=2)C=2C=C3OCOC3=CC=2)=N1 MHSGTSAQVXECLK-UHFFFAOYSA-N 0.000 claims description 5
YECDPLLJCMSCJW-UHFFFAOYSA-N 4-[3-pyridin-2-yl-1-(3-pyrrolidin-1-ylpropyl)pyrazol-4-yl]quinoline Chemical compound C1=C(C=2C3=CC=CC=C3N=CC=2)C(C=2N=CC=CC=2)=NN1CCCN1CCCC1 YECDPLLJCMSCJW-UHFFFAOYSA-N 0.000 claims description 5
ZUJOXLNMLFTWFC-UHFFFAOYSA-N 4-[3-pyridin-2-yl-1-[2-(2h-tetrazol-5-yl)ethyl]pyrazol-4-yl]quinoline Chemical compound N1=NNN=C1CCN(N=1)C=C(C=2C3=CC=CC=C3N=CC=2)C=1C1=CC=CC=N1 ZUJOXLNMLFTWFC-UHFFFAOYSA-N 0.000 claims description 5
AHSRGISWCAGSEM-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]-2-(trifluoromethyl)pyrimidine Chemical compound FC(F)(F)C1=NC=CC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=N1 AHSRGISWCAGSEM-UHFFFAOYSA-N 0.000 claims description 5
NOYRGTIDHSIQDF-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]-2-methylpyrimidine Chemical compound CC1=NC=CC(C=2C(=CNN=2)C=2C=C3OCOC3=CC=2)=N1 NOYRGTIDHSIQDF-UHFFFAOYSA-N 0.000 claims description 5
YIQGAYJYTUYZAB-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-yl)-3-(6-methylpyridin-2-yl)pyrazol-1-yl]cyclohexan-1-amine Chemical compound CC1=CC=CC(C=2C(=CN(N=2)C2CCC(N)CC2)C=2C=C3OCOC3=CC=2)=N1 YIQGAYJYTUYZAB-UHFFFAOYSA-N 0.000 claims description 5
IITIZYRMDPTJAP-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-yl)-5-(2-methylsulfanylpyrimidin-4-yl)-1h-imidazol-2-yl]benzamide Chemical compound CSC1=NC=CC(C2=C(N=C(N2)C=2C=CC(=CC=2)C(N)=O)C=2C=C3OCOC3=CC=2)=N1 IITIZYRMDPTJAP-UHFFFAOYSA-N 0.000 claims description 5
PNFODLUWBLVNJD-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-yl)-5-(2-methylsulfanylpyrimidin-4-yl)-1h-imidazol-2-yl]benzonitrile Chemical compound CSC1=NC=CC(C2=C(N=C(N2)C=2C=CC(=CC=2)C#N)C=2C=C3OCOC3=CC=2)=N1 PNFODLUWBLVNJD-UHFFFAOYSA-N 0.000 claims description 5
UREOYJDBSNWAOP-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]cyclohexan-1-amine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCC(N)CC2)C=2C=C3OCOC3=CC=2)=N1 UREOYJDBSNWAOP-UHFFFAOYSA-N 0.000 claims description 5
HRGIAZJKJVXATI-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-2h-imidazol-2-yl]-n,n-dimethylpiperidine-1-sulfonamide Chemical compound C1CN(S(=O)(=O)N(C)C)CCC1C1N=C(C=2N=C(C)C=CC=2)C(C=2C=C3OCOC3=CC=2)=N1 HRGIAZJKJVXATI-UHFFFAOYSA-N 0.000 claims description 5
ZTNXYHHZJXGCJP-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]-n-[(2,4-dichlorophenyl)methyl]piperidine-1-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1CNC(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 ZTNXYHHZJXGCJP-UHFFFAOYSA-N 0.000 claims description 5
JLVJKUWRYNTZKQ-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]-n-[(2-chlorophenyl)methyl]piperidine-1-carboxamide Chemical compound ClC1=CC=CC=C1CNC(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 JLVJKUWRYNTZKQ-UHFFFAOYSA-N 0.000 claims description 5
HHTYORXLPPYWAD-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]-n-[(3-fluorophenyl)methyl]piperidine-1-carboxamide Chemical compound FC1=CC=CC(CNC(=O)N2CCC(CC2)C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)=C1 HHTYORXLPPYWAD-UHFFFAOYSA-N 0.000 claims description 5
PYXXJCQYVKRWTJ-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]-n-[(4-fluorophenyl)methyl]piperidine-1-carboxamide Chemical compound C1=CC(F)=CC=C1CNC(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 PYXXJCQYVKRWTJ-UHFFFAOYSA-N 0.000 claims description 5
LDQVZEVRSYWYTL-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]-n-[(4-methoxyphenyl)methyl]piperidine-1-carboxamide Chemical compound C1=CC(OC)=CC=C1CNC(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 LDQVZEVRSYWYTL-UHFFFAOYSA-N 0.000 claims description 5
ISBORYSXADEHMA-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]-n-[(4-methylphenyl)methyl]piperidine-1-carboxamide Chemical compound C1=CC(C)=CC=C1CNC(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 ISBORYSXADEHMA-UHFFFAOYSA-N 0.000 claims description 5
BCYZNZMXANPOKW-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]-n-benzylpiperidine-1-carboxamide Chemical compound C1CC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CCN1C(=O)NCC1=CC=CC=C1 BCYZNZMXANPOKW-UHFFFAOYSA-N 0.000 claims description 5
FRJGDMVGTXTZSH-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]piperidine-1-carboxamide Chemical compound C1CN(C(=O)N)CCC1C1=NC(C=2C=C3OCOC3=CC=2)=C(C=2N=CC=CC=2)N1 FRJGDMVGTXTZSH-UHFFFAOYSA-N 0.000 claims description 5
QRRMLTSYWBBKFI-UHFFFAOYSA-N 4-[4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]piperidin-1-yl]sulfonylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 QRRMLTSYWBBKFI-UHFFFAOYSA-N 0.000 claims description 5
VSQHYECTXDPPSE-UHFFFAOYSA-N 4-[4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]piperidin-1-yl]sulfonylbenzonitrile Chemical compound C=1C=C(C#N)C=CC=1S(=O)(=O)N(CC1)CCC1C(N1)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CC=N1 VSQHYECTXDPPSE-UHFFFAOYSA-N 0.000 claims description 5
CVHYJFJDSMSYGH-UHFFFAOYSA-N 4-[5-(2-methylpyrimidin-4-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]cyclohexan-1-ol Chemical compound CC1=NC=CC(C2=C(N=C(N2)C2CCC(O)CC2)C=2C=C3N=CC=NC3=CC=2)=N1 CVHYJFJDSMSYGH-UHFFFAOYSA-N 0.000 claims description 5
SJANNJAOQJMQHI-UHFFFAOYSA-N 4-[5-(6-methylpyridin-2-yl)-1h-pyrazol-4-yl]-2-methylsulfanylpyrimidine Chemical compound CSC1=NC=CC(C=2C(=NNC=2)C=2N=C(C)C=CC=2)=N1 SJANNJAOQJMQHI-UHFFFAOYSA-N 0.000 claims description 5
RFDFWKWWEIPCNH-UHFFFAOYSA-N 4-[6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazolin-4-yl]morpholine Chemical compound C1COCCN1C1=NC=NC2=CC=C(C=3C(=NNC=3)C=3N=CC=CC=3)C=C12 RFDFWKWWEIPCNH-UHFFFAOYSA-N 0.000 claims description 5
XBQDWPKMVWEZHR-UHFFFAOYSA-N 4-[6-chloro-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=C(Cl)C=CC3=N2)C=2N=C(N)N=CC=2)=N1 XBQDWPKMVWEZHR-UHFFFAOYSA-N 0.000 claims description 5
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XECULGSXZDNXJQ-UHFFFAOYSA-N [2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyridin-6-yl]methanol Chemical compound CSC1=NC=CC(C=2N3C=C(CO)C=CC3=NC=2C=2N=C(C)C=CC=2)=N1 XECULGSXZDNXJQ-UHFFFAOYSA-N 0.000 claims description 5
JTTAWSWSUAVCDG-UHFFFAOYSA-N [2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyridin-6-yl]methanol Chemical compound CC1=CC=CC(C2=C(N3C=C(CO)C=CC3=N2)C=2N=C(N=CC=2)S(C)(=O)=O)=N1 JTTAWSWSUAVCDG-UHFFFAOYSA-N 0.000 claims description 5
QEQJSRLUCZMVDY-UHFFFAOYSA-N [3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-6-yl]methanol Chemical compound CC1=CC=CC(C2=C(N3C=C(CO)C=CC3=N2)C=2N=C(N)N=CC=2)=N1 QEQJSRLUCZMVDY-UHFFFAOYSA-N 0.000 claims description 5
ANTKYHGNIZRNTI-UHFFFAOYSA-N [3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-7-yl]methanol Chemical compound CC1=CC=CC(C2=C(N3C=CC(CO)=CC3=N2)C=2N=C(N)N=CC=2)=N1 ANTKYHGNIZRNTI-UHFFFAOYSA-N 0.000 claims description 5
BYAKYGFYMNEJPP-UHFFFAOYSA-N [4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-1-bicyclo[2.2.2]octanyl]methanol Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CO)(CC2)CC3)C=2C=C3OCOC3=CC=2)=N1 BYAKYGFYMNEJPP-UHFFFAOYSA-N 0.000 claims description 5
XOJFPKUVNZNOGI-UHFFFAOYSA-N [4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-1-bicyclo[2.2.2]octanyl]methyl methanesulfonate Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(COS(C)(=O)=O)(CC2)CC3)C=2C=C3OCOC3=CC=2)=N1 XOJFPKUVNZNOGI-UHFFFAOYSA-N 0.000 claims description 5
XLRLGDAZZOAPBN-UHFFFAOYSA-N [4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]piperidin-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=C(C)C=CC=2)CC1 XLRLGDAZZOAPBN-UHFFFAOYSA-N 0.000 claims description 5
IAJVXOFFUNWYCJ-UHFFFAOYSA-N [4-[5-(2-cyclopropylpyrimidin-4-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]-1-bicyclo[2.2.2]octanyl]methanol Chemical compound C1CC(CO)(CC2)CCC12C(N1)=NC(C=2C=C3N=CC=NC3=CC=2)=C1C(N=1)=CC=NC=1C1CC1 IAJVXOFFUNWYCJ-UHFFFAOYSA-N 0.000 claims description 5
SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 claims description 5
125000000732 arylene group Chemical group 0.000 claims description 5
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 5
FLPVZFWPLBCBPW-UHFFFAOYSA-N benzyl 3-[4-(1,3-benzodioxol-5-yl)-1-hydroxy-5-(6-methylpyridin-2-yl)imidazol-2-yl]piperidine-1-carboxylate Chemical compound CC1=CC=CC(C=2N(C(C3CN(CCC3)C(=O)OCC=3C=CC=CC=3)=NC=2C=2C=C3OCOC3=CC=2)O)=N1 FLPVZFWPLBCBPW-UHFFFAOYSA-N 0.000 claims description 5
UYVSVOPNRWVWOK-UHFFFAOYSA-N benzyl 3-[4-(1,3-benzodioxol-5-yl)-1-hydroxy-5-(6-methylpyridin-2-yl)imidazol-2-yl]pyrrolidine-1-carboxylate Chemical compound CC1=CC=CC(C=2N(C(C3CN(CC3)C(=O)OCC=3C=CC=CC=3)=NC=2C=2C=C3OCOC3=CC=2)O)=N1 UYVSVOPNRWVWOK-UHFFFAOYSA-N 0.000 claims description 5
YYAWRRQXTYRTBM-UHFFFAOYSA-N benzyl 3-[4-(1,3-benzodioxol-5-yl)-1-hydroxy-5-pyridin-2-ylimidazol-2-yl]piperidine-1-carboxylate Chemical compound ON1C(C2CN(CCC2)C(=O)OCC=2C=CC=CC=2)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CC=N1 YYAWRRQXTYRTBM-UHFFFAOYSA-N 0.000 claims description 5
WMRUYLMASOAKIX-UHFFFAOYSA-N benzyl 3-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]piperidine-1-carboxylate Chemical compound C1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CN1C(=O)OCC1=CC=CC=C1 WMRUYLMASOAKIX-UHFFFAOYSA-N 0.000 claims description 5
ILRMCYWSPJJDHC-UHFFFAOYSA-N benzyl 4-[4-(1,3-benzodioxol-5-yl)-1-hydroxy-5-(6-methylpyridin-2-yl)imidazol-2-yl]piperidine-1-carboxylate Chemical compound CC1=CC=CC(C=2N(C(C3CCN(CC3)C(=O)OCC=3C=CC=CC=3)=NC=2C=2C=C3OCOC3=CC=2)O)=N1 ILRMCYWSPJJDHC-UHFFFAOYSA-N 0.000 claims description 5
MXPBQVSQKIJLBS-UHFFFAOYSA-N benzyl 4-[4-(1,3-benzodioxol-5-yl)-1-methyl-5-(6-methylpyridin-2-yl)imidazol-2-yl]piperidine-1-carboxylate Chemical compound CC1=CC=CC(C=2N(C(C3CCN(CC3)C(=O)OCC=3C=CC=CC=3)=NC=2C=2C=C3OCOC3=CC=2)C)=N1 MXPBQVSQKIJLBS-UHFFFAOYSA-N 0.000 claims description 5
YDJKFBCGNSHCTN-UHFFFAOYSA-N benzyl 4-[4-(1,3-benzodioxol-5-yl)-5-(6-ethylpyridin-2-yl)-1h-imidazol-2-yl]piperidine-1-carboxylate Chemical compound CCC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)C(=O)OCC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 YDJKFBCGNSHCTN-UHFFFAOYSA-N 0.000 claims description 5
RCCQRLHHHFFQTG-UHFFFAOYSA-N benzyl 4-[4-(1,3-benzodioxol-5-yl)-5-[6-(trifluoromethyl)pyridin-2-yl]-1h-imidazol-2-yl]piperidine-1-carboxylate Chemical compound FC(F)(F)C1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)C(=O)OCC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 RCCQRLHHHFFQTG-UHFFFAOYSA-N 0.000 claims description 5
PBPHCFMNDCXBPN-UHFFFAOYSA-N benzyl 4-[5-(1,3-benzodioxol-5-yl)-1-hydroxy-4-(6-methylpyridin-2-yl)imidazol-2-yl]piperidine-1-carboxylate Chemical compound CC1=CC=CC(C2=C(N(O)C(C3CCN(CC3)C(=O)OCC=3C=CC=CC=3)=N2)C=2C=C3OCOC3=CC=2)=N1 PBPHCFMNDCXBPN-UHFFFAOYSA-N 0.000 claims description 5
ZEMXQOXSUMNQJR-UHFFFAOYSA-N benzyl 4-[5-(1,3-benzodioxol-5-yl)-1-methyl-4-(6-methylpyridin-2-yl)imidazol-2-yl]piperidine-1-carboxylate Chemical compound CC1=CC=CC(C2=C(N(C)C(C3CCN(CC3)C(=O)OCC=3C=CC=CC=3)=N2)C=2C=C3OCOC3=CC=2)=N1 ZEMXQOXSUMNQJR-UHFFFAOYSA-N 0.000 claims description 5
FGLYBAMPQJQWRN-UHFFFAOYSA-N benzyl 4-[5-(1,3-benzodioxol-5-yl)-4-(6-bromopyridin-2-yl)-1-hydroxyimidazol-2-yl]piperidine-1-carboxylate Chemical compound C=1C=C2OCOC2=CC=1C=1N(O)C(C2CCN(CC2)C(=O)OCC=2C=CC=CC=2)=NC=1C1=CC=CC(Br)=N1 FGLYBAMPQJQWRN-UHFFFAOYSA-N 0.000 claims description 5
AYBAYRSDQLKGBA-UHFFFAOYSA-N benzyl 4-[5-(2-cyclopropylpyrimidin-4-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]piperidine-1-carboxylate Chemical compound C1CC(C=2NC(=C(N=2)C=2C=C3N=CC=NC3=CC=2)C=2N=C(N=CC=2)C2CC2)CCN1C(=O)OCC1=CC=CC=C1 AYBAYRSDQLKGBA-UHFFFAOYSA-N 0.000 claims description 5
KYTOWRQDSUTQEP-UHFFFAOYSA-N benzyl n-[1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-4-bicyclo[2.2.2]octanyl]carbamate Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)NC(=O)OCC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 KYTOWRQDSUTQEP-UHFFFAOYSA-N 0.000 claims description 5
HGVJKJTWVKWHNL-UHFFFAOYSA-N benzyl n-[1-[5-[2-(cyclopropylamino)pyrimidin-4-yl]-4-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-4-bicyclo[2.2.2]octanyl]carbamate Chemical compound CC1=CC=CC(C2=C(NC(=N2)C23CCC(CC2)(CC3)NC(=O)OCC=2C=CC=CC=2)C=2N=C(NC3CC3)N=CC=2)=N1 HGVJKJTWVKWHNL-UHFFFAOYSA-N 0.000 claims description 5
NUNPIJGMCBURAP-UHFFFAOYSA-N benzyl n-[4-[4-(1,3-benzodioxol-5-yl)-1-hydroxy-5-(6-methylpyridin-2-yl)imidazol-2-yl]cyclohexyl]carbamate Chemical compound CC1=CC=CC(C=2N(C(C3CCC(CC3)NC(=O)OCC=3C=CC=CC=3)=NC=2C=2C=C3OCOC3=CC=2)O)=N1 NUNPIJGMCBURAP-UHFFFAOYSA-N 0.000 claims description 5
HKDZSCRAUDDTJO-UHFFFAOYSA-N benzyl n-[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]cyclohexyl]carbamate Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCC(CC2)NC(=O)OCC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 HKDZSCRAUDDTJO-UHFFFAOYSA-N 0.000 claims description 5
BFSIPABIKNTDAL-UHFFFAOYSA-N benzyl n-[4-[5-(6-methylpyridin-2-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]cyclohexyl]carbamate Chemical compound CC1=CC=CC(C2=C(NC(=N2)C2CCC(CC2)NC(=O)OCC=2C=CC=CC=2)C=2C=C3N=CC=NC3=CC=2)=N1 BFSIPABIKNTDAL-UHFFFAOYSA-N 0.000 claims description 5
NTKOFBLZGJHQLV-UHFFFAOYSA-N benzyl n-[[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]cyclohexyl]methyl]carbamate Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCC(CNC(=O)OCC=3C=CC=CC=3)CC2)C=2C=C3OCOC3=CC=2)=N1 NTKOFBLZGJHQLV-UHFFFAOYSA-N 0.000 claims description 5
229910052799 carbon Inorganic materials 0.000 claims description 5
125000005724 cycloalkenylene group Chemical group 0.000 claims description 5
125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 5
125000002993 cycloalkylene group Chemical group 0.000 claims description 5
QFHMDQXPBKJJRC-UHFFFAOYSA-N ethyl 2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyridine-7-carboxylate Chemical compound N1=C2C=C(C(=O)OCC)C=CN2C(C=2N=C(SC)N=CC=2)=C1C1=CC=CC(C)=N1 QFHMDQXPBKJJRC-UHFFFAOYSA-N 0.000 claims description 5
MLLZUQFQTCAQEX-UHFFFAOYSA-N ethyl 2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyridine-7-carboxylate Chemical compound N1=C2C=C(C(=O)OCC)C=CN2C(C=2N=C(N=CC=2)S(C)(=O)=O)=C1C1=CC=CC(C)=N1 MLLZUQFQTCAQEX-UHFFFAOYSA-N 0.000 claims description 5
UDYZIFHYNMPZCV-UHFFFAOYSA-N ethyl 2-[[4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]piperidin-1-yl]methyl]cyclopropane-1-carboxylate Chemical compound CCOC(=O)C1CC1CN1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 UDYZIFHYNMPZCV-UHFFFAOYSA-N 0.000 claims description 5
IGVJTFHMBDHFBX-UHFFFAOYSA-N ethyl 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxylate Chemical compound N1=C2C=C(C(=O)OCC)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 IGVJTFHMBDHFBX-UHFFFAOYSA-N 0.000 claims description 5
125000005549 heteroarylene group Chemical group 0.000 claims description 5
125000006588 heterocycloalkylene group Chemical group 0.000 claims description 5
125000005946 imidazo[1,2-a]pyridyl group Chemical group 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
MUIPEBFNXITVRC-UHFFFAOYSA-N methyl 1-[4-(1,3-benzodioxol-5-yl)-1-hydroxy-5-(6-methylpyridin-2-yl)imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylate Chemical compound C1CC(C(=O)OC)(CC2)CCC12C(N1O)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CC(C)=N1 MUIPEBFNXITVRC-UHFFFAOYSA-N 0.000 claims description 5
MLNIHAZFATZMLC-UHFFFAOYSA-N methyl 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylate Chemical compound C1CC(C(=O)OC)(CC2)CCC12C(N1)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CC(C)=N1 MLNIHAZFATZMLC-UHFFFAOYSA-N 0.000 claims description 5
YNWJWINZGPMSOV-UHFFFAOYSA-N methyl 1-[4-(3-methyl-4-oxoquinazolin-6-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylate Chemical compound C1CC(C(=O)OC)(CC2)CCC12C(NC=1C=2C=C3C(=O)N(C)C=NC3=CC=2)=NC=1C1=CC=CC(C)=N1 YNWJWINZGPMSOV-UHFFFAOYSA-N 0.000 claims description 5
SHEAUYBYKARAME-UHFFFAOYSA-N methyl 1-[4-(6-methylpyridin-2-yl)-5-(2-methylsulfonylpyrimidin-4-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylate Chemical compound C1CC(C(=O)OC)(CC2)CCC12C(N1)=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(S(C)(=O)=O)=N1 SHEAUYBYKARAME-UHFFFAOYSA-N 0.000 claims description 5
JPUNLPDLHYEFHG-UHFFFAOYSA-N methyl 1-[4-(6-methylpyridin-2-yl)-5-(2-oxo-1h-pyrimidin-6-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylate Chemical compound C1CC(C(=O)OC)(CC2)CCC12C(N1)=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(=O)N1 JPUNLPDLHYEFHG-UHFFFAOYSA-N 0.000 claims description 5
VGUBUAAMYIJYSJ-UHFFFAOYSA-N methyl 1-[5-(2-methoxypyrimidin-4-yl)-4-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylate Chemical compound C1CC(C(=O)OC)(CC2)CCC12C(N1)=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(OC)=N1 VGUBUAAMYIJYSJ-UHFFFAOYSA-N 0.000 claims description 5
QRNGIZIVLZGQPW-UHFFFAOYSA-N methyl 1-[5-(2-methylpyrimidin-4-yl)-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylate Chemical compound C1CC(C(=O)OC)(CC2)CCC12C(N1)=NC(C2=CN3N=CN=C3C=C2)=C1C1=CC=NC(C)=N1 QRNGIZIVLZGQPW-UHFFFAOYSA-N 0.000 claims description 5
VDOQHHCXPVJPQV-UHFFFAOYSA-N methyl 1-[5-(5-fluoro-6-methylpyridin-2-yl)-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylate Chemical compound C1CC(C(=O)OC)(CC2)CCC12C(NC=1C2=CN3N=CN=C3C=C2)=NC=1C1=CC=C(F)C(C)=N1 VDOQHHCXPVJPQV-UHFFFAOYSA-N 0.000 claims description 5
NWFVHIKWHVMBEH-UHFFFAOYSA-N methyl 1-[5-(6-cyclopropylpyridin-2-yl)-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylate Chemical compound C1CC(C(=O)OC)(CC2)CCC12C(NC=1C2=CN3N=CN=C3C=C2)=NC=1C(N=1)=CC=CC=1C1CC1 NWFVHIKWHVMBEH-UHFFFAOYSA-N 0.000 claims description 5
FDJOWQXTDJWMPC-UHFFFAOYSA-N methyl 1-[5-(6-methylpyridin-2-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylate Chemical compound C1CC(C(=O)OC)(CC2)CCC12C(NC=1C=2C=C3N=CC=NC3=CC=2)=NC=1C1=CC=CC(C)=N1 FDJOWQXTDJWMPC-UHFFFAOYSA-N 0.000 claims description 5
BONOOAYCHZZVND-UHFFFAOYSA-N methyl 1-[5-[2-(cyclopropylamino)pyrimidin-4-yl]-4-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylate Chemical compound C1CC(C(=O)OC)(CC2)CCC12C(N1)=NC(C=2N=C(C)C=CC=2)=C1C(N=1)=CC=NC=1NC1CC1 BONOOAYCHZZVND-UHFFFAOYSA-N 0.000 claims description 5
HUFJMAZLBLCKBL-UHFFFAOYSA-N methyl 2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyridine-6-carboxylate Chemical compound N12C=C(C(=O)OC)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(SC)=N1 HUFJMAZLBLCKBL-UHFFFAOYSA-N 0.000 claims description 5
PGCUQJWVGDBCCN-UHFFFAOYSA-N methyl 2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyridine-6-carboxylate Chemical compound N12C=C(C(=O)OC)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(S(C)(=O)=O)=N1 PGCUQJWVGDBCCN-UHFFFAOYSA-N 0.000 claims description 5
VVALHDDBBJJYDI-UHFFFAOYSA-N methyl 3-[[3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carbonyl]amino]propanoate Chemical compound N12C=C(C(=O)NCCC(=O)OC)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(N)=N1 VVALHDDBBJJYDI-UHFFFAOYSA-N 0.000 claims description 5
WSIRNNCRNKOMOB-UHFFFAOYSA-N methyl 3-[[3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carbonyl]amino]propanoate Chemical compound N1=C2C=C(C(=O)NCCC(=O)OC)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 WSIRNNCRNKOMOB-UHFFFAOYSA-N 0.000 claims description 5
ZVTWQRWEZQTOQF-UHFFFAOYSA-N methyl 4-[2-[2-[4-(1,3-benzodioxol-5-yl)-3-(6-methylpyridin-2-yl)pyrazol-1-yl]ethoxy]ethoxy]bicyclo[2.2.2]octane-1-carboxylate Chemical compound C1CC(C(=O)OC)(CC2)CCC12OCCOCCN(N=1)C=C(C=2C=C3OCOC3=CC=2)C=1C1=CC=CC(C)=N1 ZVTWQRWEZQTOQF-UHFFFAOYSA-N 0.000 claims description 5
VCQMZOLWWYQBIZ-UHFFFAOYSA-N methyl 4-[4-(1,3-benzodioxol-5-yl)-3-(6-methylpyridin-2-yl)pyrazol-1-yl]bicyclo[2.2.2]octane-1-carboxylate Chemical compound C1CC(C(=O)OC)(CC2)CCC12N(N=1)C=C(C=2C=C3OCOC3=CC=2)C=1C1=CC=CC(C)=N1 VCQMZOLWWYQBIZ-UHFFFAOYSA-N 0.000 claims description 5
SKUDIQGDJCJNBP-UHFFFAOYSA-N n',n'-dimethyl-n-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]ethane-1,2-diamine Chemical compound CN(C)CCNC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 SKUDIQGDJCJNBP-UHFFFAOYSA-N 0.000 claims description 5
PLPJZUFRCQISJL-UHFFFAOYSA-N n,n-dimethyl-3-(3-pyridin-2-yl-4-quinolin-4-ylpyrazol-1-yl)propan-1-amine Chemical compound N=1N(CCCN(C)C)C=C(C=2C3=CC=CC=C3N=CC=2)C=1C1=CC=CC=N1 PLPJZUFRCQISJL-UHFFFAOYSA-N 0.000 claims description 5
LHBQJBASKOAGGW-UHFFFAOYSA-N n,n-dimethyl-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CN(C)C1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 LHBQJBASKOAGGW-UHFFFAOYSA-N 0.000 claims description 5
NSXRXTQIPOLKAQ-UHFFFAOYSA-N n,n-dimethyl-5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)N(C)C)=NNC2=CC=C1C1=CNN=C1C1=CC=CC=N1 NSXRXTQIPOLKAQ-UHFFFAOYSA-N 0.000 claims description 5
ATZVYFZDGMLQDL-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)-1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(=O)NC=2NC3=CC=CC=C3N=2)C=2C=C3OCOC3=CC=2)=N1 ATZVYFZDGMLQDL-UHFFFAOYSA-N 0.000 claims description 5
JADDVONWNKKVFF-UHFFFAOYSA-N n-(2,2-dimethylpropyl)-5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)NCC(C)(C)C)=NNC2=CC=C1C=1C=NNC=1C1=CC=CC=N1 JADDVONWNKKVFF-UHFFFAOYSA-N 0.000 claims description 5
WWSCCUJUUTZBPL-UHFFFAOYSA-N n-(2-methoxyethyl)-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound COCCNC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 WWSCCUJUUTZBPL-UHFFFAOYSA-N 0.000 claims description 5
IMZHFBNWTRKGPJ-UHFFFAOYSA-N n-(3-imidazol-1-ylpropyl)-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCN3C=NC=C3)N=CC=2)=N1 IMZHFBNWTRKGPJ-UHFFFAOYSA-N 0.000 claims description 5
PCCDINVHZJGVQS-UHFFFAOYSA-N n-(4-morpholin-4-ylphenyl)-6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazolin-4-amine Chemical compound C1COCCN1C(C=C1)=CC=C1NC1=NC=NC2=CC=C(C=3C(=NNC=3)C=3N=CC=CC=3)C=C12 PCCDINVHZJGVQS-UHFFFAOYSA-N 0.000 claims description 5
RQLBSRWECGGUKO-UHFFFAOYSA-N n-[(4-aminophenyl)methyl]-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCC=3C=CC(N)=CC=3)N=CC=2)=N1 RQLBSRWECGGUKO-UHFFFAOYSA-N 0.000 claims description 5
LZZKVZNLUYDCJN-UHFFFAOYSA-N n-[1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-4-bicyclo[2.2.2]octanyl]-1-methylimidazole-4-sulfonamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)NS(=O)(=O)C=2N=CN(C)C=2)C=2C=C3OCOC3=CC=2)=N1 LZZKVZNLUYDCJN-UHFFFAOYSA-N 0.000 claims description 5
BNEKNFBLMPBYDD-UHFFFAOYSA-N n-[1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-4-bicyclo[2.2.2]octanyl]-1-phenylmethanesulfonamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)NS(=O)(=O)CC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 BNEKNFBLMPBYDD-UHFFFAOYSA-N 0.000 claims description 5
WXIRAUQWCUZUEN-UHFFFAOYSA-N n-[1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-4-bicyclo[2.2.2]octanyl]-1-pyridin-2-ylmethanesulfonamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)NS(=O)(=O)CC=2N=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 WXIRAUQWCUZUEN-UHFFFAOYSA-N 0.000 claims description 5
OCBBSNQNKKGPDP-UHFFFAOYSA-N n-[1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-4-bicyclo[2.2.2]octanyl]acetamide Chemical compound C1CC(NC(=O)C)(CC2)CCC12C(N1)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CC(C)=N1 OCBBSNQNKKGPDP-UHFFFAOYSA-N 0.000 claims description 5
FZEJDYTUUDDWPT-UHFFFAOYSA-N n-[1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-4-bicyclo[2.2.2]octanyl]thiophene-2-sulfonamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)NS(=O)(=O)C=2SC=CC=2)C=2C=C3OCOC3=CC=2)=N1 FZEJDYTUUDDWPT-UHFFFAOYSA-N 0.000 claims description 5
FLFUCQHZGVBFDA-UHFFFAOYSA-N n-[1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-4-bicyclo[2.2.2]octanyl]thiophene-3-sulfonamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)NS(=O)(=O)C2=CSC=C2)C=2C=C3OCOC3=CC=2)=N1 FLFUCQHZGVBFDA-UHFFFAOYSA-N 0.000 claims description 5
XAUGBHAXFOOAIF-UHFFFAOYSA-N n-[1-[5-(6-methylpyridin-2-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]-4-bicyclo[2.2.2]octanyl]acetamide Chemical compound C1CC(NC(=O)C)(CC2)CCC12C(N1)=NC(C=2C=C3N=CC=NC3=CC=2)=C1C1=CC=CC(C)=N1 XAUGBHAXFOOAIF-UHFFFAOYSA-N 0.000 claims description 5
CPXWHQHMPSLSIT-UHFFFAOYSA-N n-[1-[5-(6-methylpyridin-2-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]-4-bicyclo[2.2.2]octanyl]methanesulfonamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)NS(C)(=O)=O)C=2C=C3N=CC=NC3=CC=2)=N1 CPXWHQHMPSLSIT-UHFFFAOYSA-N 0.000 claims description 5
CIJIVQDXYSUZPF-UHFFFAOYSA-N n-[2-(3-pyridin-2-yl-4-quinolin-4-ylpyrazol-1-yl)ethyl]methanesulfonamide Chemical compound N=1N(CCNS(=O)(=O)C)C=C(C=2C3=CC=CC=C3N=CC=2)C=1C1=CC=CC=N1 CIJIVQDXYSUZPF-UHFFFAOYSA-N 0.000 claims description 5
IHMOMVMNTVXNDN-UHFFFAOYSA-N n-[2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl]-3-pyridin-3-ylpropanamide Chemical compound CSC1=NC=CC(C=2N3C=CC(NC(=O)CCC=4C=NC=CC=4)=NC3=NC=2C=2N=C(C)C=CC=2)=N1 IHMOMVMNTVXNDN-UHFFFAOYSA-N 0.000 claims description 5
WEVPRMMAVXDFRH-UHFFFAOYSA-N n-[2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl]propanamide Chemical compound N1=C2N=C(NC(=O)CC)C=CN2C(C=2N=C(N=CC=2)S(C)(=O)=O)=C1C1=CC=CC(C)=N1 WEVPRMMAVXDFRH-UHFFFAOYSA-N 0.000 claims description 5
UVHPZRONHYJPKH-UHFFFAOYSA-N n-[2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl]pyridine-3-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(NC(=O)C=4C=NC=CC=4)=NC3=N2)C=2N=C(N=CC=2)S(C)(=O)=O)=N1 UVHPZRONHYJPKH-UHFFFAOYSA-N 0.000 claims description 5
YYAVSZGFEPUTHP-UHFFFAOYSA-N n-[3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyrimidin-7-yl]-2-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(CC(=O)NC2=NC3=NC(=C(N3C=C2)C=2N=C(N)N=CC=2)C=2N=C(C)C=CC=2)=C1 YYAVSZGFEPUTHP-UHFFFAOYSA-N 0.000 claims description 5
JDBVSUUJSFDFFW-UHFFFAOYSA-N n-[3-(3-pyridin-2-yl-4-quinolin-4-ylpyrazol-1-yl)propyl]acetamide Chemical compound N=1N(CCCNC(=O)C)C=C(C=2C3=CC=CC=C3N=CC=2)C=1C1=CC=CC=N1 JDBVSUUJSFDFFW-UHFFFAOYSA-N 0.000 claims description 5
UFFLRNPZBQSJLA-UHFFFAOYSA-N n-[3-(3-pyridin-2-yl-4-quinolin-4-ylpyrazol-1-yl)propyl]methanesulfonamide Chemical compound N=1N(CCCNS(=O)(=O)C)C=C(C=2C3=CC=CC=C3N=CC=2)C=1C1=CC=CC=N1 UFFLRNPZBQSJLA-UHFFFAOYSA-N 0.000 claims description 5
MCXIJRXEPGHSNX-UHFFFAOYSA-N n-[3-(4-methylpiperazin-1-yl)propyl]-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1CN(C)CCN1CCCNC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 MCXIJRXEPGHSNX-UHFFFAOYSA-N 0.000 claims description 5
JYJCLZJDOYHSJZ-UHFFFAOYSA-N n-[3-(4-methylpiperidin-1-yl)propyl]-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1CC(C)CCN1CCCNC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 JYJCLZJDOYHSJZ-UHFFFAOYSA-N 0.000 claims description 5
YLONOLZALBGKKB-UHFFFAOYSA-N n-[3-[4-(1,3-benzodioxol-5-yl)-3-(6-methylpyridin-2-yl)pyrazol-1-yl]propyl]methanesulfonamide Chemical compound CC1=CC=CC(C=2C(=CN(CCCNS(C)(=O)=O)N=2)C=2C=C3OCOC3=CC=2)=N1 YLONOLZALBGKKB-UHFFFAOYSA-N 0.000 claims description 5
WZEQZQOEXMACDP-UHFFFAOYSA-N n-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]-1,3,4-thiadiazol-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NC=3SC=NN=3)N=CC=2)=N1 WZEQZQOEXMACDP-UHFFFAOYSA-N 0.000 claims description 5
YQTXBCQGMQIFHA-UHFFFAOYSA-N n-[4-[4-(1,3-benzodioxol-5-yl)-3-(6-methylpyridin-2-yl)pyrazol-1-yl]cyclohexyl]methanesulfonamide Chemical compound CC1=CC=CC(C=2C(=CN(N=2)C2CCC(CC2)NS(C)(=O)=O)C=2C=C3OCOC3=CC=2)=N1 YQTXBCQGMQIFHA-UHFFFAOYSA-N 0.000 claims description 5
VZLCIGZSUBXKFU-UHFFFAOYSA-N n-[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]cyclohexyl]-1-methylimidazole-4-sulfonamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCC(CC2)NS(=O)(=O)C=2N=CN(C)C=2)C=2C=C3OCOC3=CC=2)=N1 VZLCIGZSUBXKFU-UHFFFAOYSA-N 0.000 claims description 5
BNRHAYBJQHUPFO-UHFFFAOYSA-N n-[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]cyclohexyl]butane-1-sulfonamide Chemical compound C1CC(NS(=O)(=O)CCCC)CCC1C1=NC(C=2C=C3OCOC3=CC=2)=C(C=2N=C(C)C=CC=2)N1 BNRHAYBJQHUPFO-UHFFFAOYSA-N 0.000 claims description 5
SQAMQHSJXJSQPS-UHFFFAOYSA-N n-[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]cyclohexyl]thiophene-2-sulfonamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCC(CC2)NS(=O)(=O)C=2SC=CC=2)C=2C=C3OCOC3=CC=2)=N1 SQAMQHSJXJSQPS-UHFFFAOYSA-N 0.000 claims description 5
SSOWKIPDUUSTQR-UHFFFAOYSA-N n-[4-[5-(6-methylpyridin-2-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]cyclohexyl]methanesulfonamide Chemical compound CC1=CC=CC(C2=C(NC(=N2)C2CCC(CC2)NS(C)(=O)=O)C=2C=C3N=CC=NC3=CC=2)=N1 SSOWKIPDUUSTQR-UHFFFAOYSA-N 0.000 claims description 5
COZHHCCXEPKUPS-UHFFFAOYSA-N n-[[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-1-bicyclo[2.2.2]octanyl]methyl]-1-phenylmethanesulfonamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CNS(=O)(=O)CC=4C=CC=CC=4)(CC2)CC3)C=2C=C3OCOC3=CC=2)=N1 COZHHCCXEPKUPS-UHFFFAOYSA-N 0.000 claims description 5
HLEPPLCYOPROMT-UHFFFAOYSA-N n-[[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]cyclohexyl]methyl]-1-phenylmethanesulfonamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCC(CNS(=O)(=O)CC=3C=CC=CC=3)CC2)C=2C=C3OCOC3=CC=2)=N1 HLEPPLCYOPROMT-UHFFFAOYSA-N 0.000 claims description 5
ILVOUIRNTYMOBH-UHFFFAOYSA-N n-[[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]cyclohexyl]methyl]-1-pyridin-2-ylmethanesulfonamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCC(CNS(=O)(=O)CC=3N=CC=CC=3)CC2)C=2C=C3OCOC3=CC=2)=N1 ILVOUIRNTYMOBH-UHFFFAOYSA-N 0.000 claims description 5
KAYVCFMKCMLIDK-UHFFFAOYSA-N n-[[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]cyclohexyl]methyl]-1-pyridin-4-ylmethanesulfonamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCC(CNS(=O)(=O)CC=3C=CN=CC=3)CC2)C=2C=C3OCOC3=CC=2)=N1 KAYVCFMKCMLIDK-UHFFFAOYSA-N 0.000 claims description 5
OGDDSGBJTFBANP-UHFFFAOYSA-N n-[[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]cyclohexyl]methyl]acetamide Chemical compound C1CC(CNC(=O)C)CCC1C1=NC(C=2C=C3OCOC3=CC=2)=C(C=2N=C(C)C=CC=2)N1 OGDDSGBJTFBANP-UHFFFAOYSA-N 0.000 claims description 5
YPDUTSPYVABKFP-UHFFFAOYSA-N n-[[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]cyclohexyl]methyl]methanesulfonamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCC(CNS(C)(=O)=O)CC2)C=2C=C3OCOC3=CC=2)=N1 YPDUTSPYVABKFP-UHFFFAOYSA-N 0.000 claims description 5
HQUAVNGZXPDBGG-UHFFFAOYSA-N n-benzyl-5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-1h-indazole-3-carboxamide Chemical compound N=1NC2=CC=C(C=3C(=NNC=3)C=3N=CC=CC=3)C=C2C=1C(=O)NCC1=CC=CC=C1 HQUAVNGZXPDBGG-UHFFFAOYSA-N 0.000 claims description 5
XNAAOIBANVQHDR-UHFFFAOYSA-N n-cyclopentyl-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NC3CCCC3)N=CC=2)=N1 XNAAOIBANVQHDR-UHFFFAOYSA-N 0.000 claims description 5
BOZKLPKKXYBXKP-UHFFFAOYSA-N n-cyclopropyl-n-methyl-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound N=1C=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=NC=1N(C)C1CC1 BOZKLPKKXYBXKP-UHFFFAOYSA-N 0.000 claims description 5
HPDIJGLJVPCQPX-UHFFFAOYSA-N n-hydroxy-1-[5-(6-methylpyridin-2-yl)-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(NC(=N2)C23CCC(CC2)(CC3)C(=O)NO)C2=CN3N=CN=C3C=C2)=N1 HPDIJGLJVPCQPX-UHFFFAOYSA-N 0.000 claims description 5
SJVMSBCSXJCECY-UHFFFAOYSA-N n-hydroxy-1-[5-(6-methylpyridin-2-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(NC(=N2)C23CCC(CC2)(CC3)C(=O)NO)C=2C=C3N=CC=NC3=CC=2)=N1 SJVMSBCSXJCECY-UHFFFAOYSA-N 0.000 claims description 5
TVGHQAZJZCDHCM-UHFFFAOYSA-N n-hydroxy-3-(3-pyridin-2-yl-4-quinolin-4-ylpyrazol-1-yl)propanamide Chemical compound N=1N(CCC(=O)NO)C=C(C=2C3=CC=CC=C3N=CC=2)C=1C1=CC=CC=N1 TVGHQAZJZCDHCM-UHFFFAOYSA-N 0.000 claims description 5
RRRGHOSHLCPQLU-UHFFFAOYSA-N n-methyl-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CNC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 RRRGHOSHLCPQLU-UHFFFAOYSA-N 0.000 claims description 5
QMDPZBJUHORZHH-UHFFFAOYSA-N n-methyl-5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-1h-indazole-3-carboxamide Chemical compound C1=C2C(C(=O)NC)=NNC2=CC=C1C1=CNN=C1C1=CC=CC=N1 QMDPZBJUHORZHH-UHFFFAOYSA-N 0.000 claims description 5
VGXNKFNLPSVFAI-UHFFFAOYSA-N n-phenyl-5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-1h-indazole-3-carboxamide Chemical compound N=1NC2=CC=C(C3=C(NN=C3)C=3N=CC=CC=3)C=C2C=1C(=O)NC1=CC=CC=C1 VGXNKFNLPSVFAI-UHFFFAOYSA-N 0.000 claims description 5
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
ZVKRNQYPRSEQLT-UHFFFAOYSA-N tert-butyl 2-[[4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]piperidin-1-yl]methyl]pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1CN1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 ZVKRNQYPRSEQLT-UHFFFAOYSA-N 0.000 claims description 5
KSGUWWVYVKIXKD-UHFFFAOYSA-N tert-butyl n-[4-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]butyl]carbamate Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCCNC(=O)OC(C)(C)C)N=CC=2)=N1 KSGUWWVYVKIXKD-UHFFFAOYSA-N 0.000 claims description 5
GJXUUDPBMCBINS-UHFFFAOYSA-N tert-butyl n-[5-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]pentyl]carbamate Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCCCNC(=O)OC(C)(C)C)N=CC=2)=N1 GJXUUDPBMCBINS-UHFFFAOYSA-N 0.000 claims description 5
125000000464 thioxo group Chemical group S=* 0.000 claims description 5
FXPNNBPYKCSUKM-UHFFFAOYSA-N (4-methoxyphenyl)-[6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazolin-4-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=NC=NC2=CC=C(C=3C(=NNC=3)C=3N=CC=CC=3)C=C12 FXPNNBPYKCSUKM-UHFFFAOYSA-N 0.000 claims description 4
VCCKBRVPZFATNP-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-1-hydroxy-5-(6-methylpyridin-2-yl)imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C=2N(C(=NC=2C=2C=C3OCOC3=CC=2)C23CCC(CC2)(CC3)C(N)=O)O)=N1 VCCKBRVPZFATNP-UHFFFAOYSA-N 0.000 claims description 4
JJNJCSWAUNUNME-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-cyclohexylbicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(=O)NC2CCCCC2)C=2C=C3OCOC3=CC=2)=N1 JJNJCSWAUNUNME-UHFFFAOYSA-N 0.000 claims description 4
FQKPLAVROJGWCP-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carbohydrazide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(=O)NN)C=2C=C3OCOC3=CC=2)=N1 FQKPLAVROJGWCP-UHFFFAOYSA-N 0.000 claims description 4
MPBWLALQULSSSD-UHFFFAOYSA-N 1-[4-(3-methyl-4-oxoquinazolin-6-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(NC(=N2)C23CCC(CC2)(CC3)C(N)=O)C=2C=C3C(=O)N(C)C=NC3=CC=2)=N1 MPBWLALQULSSSD-UHFFFAOYSA-N 0.000 claims description 4
ZYTPHJMFJJGFAE-UHFFFAOYSA-N 1-[5-(2-methylpyrimidin-4-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]bicyclo[2.2.2]octan-4-ol Chemical compound CC1=NC=CC(C2=C(N=C(N2)C23CCC(O)(CC2)CC3)C=2C=C3N=CC=NC3=CC=2)=N1 ZYTPHJMFJJGFAE-UHFFFAOYSA-N 0.000 claims description 4
WJADENHXXXGFQC-UHFFFAOYSA-N 1-[5-(6-cyclopropylpyridin-2-yl)-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxamide Chemical compound C1CC(C(=O)N)(CC2)CCC12C(NC=1C2=CN3N=CN=C3C=C2)=NC=1C(N=1)=CC=CC=1C1CC1 WJADENHXXXGFQC-UHFFFAOYSA-N 0.000 claims description 4
SDJBBSCKFMBPRN-UHFFFAOYSA-N 1-[5-(6-methylpyridin-2-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(NC(=N2)C23CCC(CC2)(CC3)C(N)=O)C=2C=C3N=CC=NC3=CC=2)=N1 SDJBBSCKFMBPRN-UHFFFAOYSA-N 0.000 claims description 4
GIJBVTBOMJGKKK-UHFFFAOYSA-N 2-(3-amino-6-iminoxanthen-9-yl)-4-[4-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]butylcarbamoyl]benzoic acid Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCCNC(=O)C=3C=C(C(C(O)=O)=CC=3)C3=C4C=CC(=N)C=C4OC4=CC(N)=CC=C43)N=CC=2)=N1 GIJBVTBOMJGKKK-UHFFFAOYSA-N 0.000 claims description 4
SBOQNZCQEFSIBJ-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-propylsulfonylpiperidin-4-yl)-1h-imidazol-5-yl]pyridine Chemical compound C1CN(S(=O)(=O)CCC)CCC1C1=NC(C=2C=C3OCOC3=CC=2)=C(C=2N=CC=CC=2)N1 SBOQNZCQEFSIBJ-UHFFFAOYSA-N 0.000 claims description 4
ZFHPVSVBYUVQQV-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(1-methylimidazol-4-yl)sulfonylpiperidin-4-yl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)C=2N=CN(C)C=2)C=2C=C3OCOC3=CC=2)=N1 ZFHPVSVBYUVQQV-UHFFFAOYSA-N 0.000 claims description 4
JKRBSKGJJHPDKW-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(4-phenoxyphenyl)sulfonylpiperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C=1C=C(OC=2C=CC=CC=2)C=CC=1S(=O)(=O)N(CC1)CCC1C(N1)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CC=N1 JKRBSKGJJHPDKW-UHFFFAOYSA-N 0.000 claims description 4
VTNZDIXVWUFWCR-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[4-(2h-tetrazol-5-yl)-1-bicyclo[2.2.2]octanyl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C=2NN=NN=2)C=2C=C3OCOC3=CC=2)=N1 VTNZDIXVWUFWCR-UHFFFAOYSA-N 0.000 claims description 4
UFOODNGHDAVHSP-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-5-(trifluoromethyl)-1h-pyrazol-3-yl]-6-bromopyridine Chemical compound C=1C=C2OCOC2=CC=1C1=C(C(F)(F)F)NN=C1C1=CC=CC(Br)=N1 UFOODNGHDAVHSP-UHFFFAOYSA-N 0.000 claims description 4
FEBFVHXQOMKXJX-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)-n-(2-thiophen-2-ylethyl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NCCC=2SC=CC=2)C=2N=C(N)N=CC=2)=N1 FEBFVHXQOMKXJX-UHFFFAOYSA-N 0.000 claims description 4
GRZYOCPOBQZHDY-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-6-methyl-2-(6-methylpyridin-2-yl)-n-(2-morpholin-4-ylethyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C12=NC(C=3N=C(C)C=CC=3)=C(C=3N=C(N)N=CC=3)N2C=C(C)C=C1NCCN1CCOCC1 GRZYOCPOBQZHDY-UHFFFAOYSA-N 0.000 claims description 4
YWJXDLAGSVQNRE-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-6-methyl-2-(6-methylpyridin-2-yl)-n-(2-pyridin-3-ylethyl)imidazo[1,2-a]pyridin-8-amine Chemical compound C12=NC(C=3N=C(C)C=CC=3)=C(C=3N=C(N)N=CC=3)N2C=C(C)C=C1NCCC1=CC=CN=C1 YWJXDLAGSVQNRE-UHFFFAOYSA-N 0.000 claims description 4
MPPCLPUSEFDPGS-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-(1,4-dioxan-2-ylmethyl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NCC2OCCOC2)C=2N=C(N)N=CC=2)=N1 MPPCLPUSEFDPGS-UHFFFAOYSA-N 0.000 claims description 4
WSEICPQOLNGCPR-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)-8-phenylmethoxyimidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=C(OCC=4C=CC=CC=4)C3=N2)C=2N=C(N)N=CC=2)=N1 WSEICPQOLNGCPR-UHFFFAOYSA-N 0.000 claims description 4
VENUMYHILKBIGQ-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)pyrazolo[1,5-c]pyrimidin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C=2C(=C3C=CN=CN3N=2)C=2N=C(N)N=CC=2)=N1 VENUMYHILKBIGQ-UHFFFAOYSA-N 0.000 claims description 4
DPICOUUHHUBYDI-UHFFFAOYSA-N 6-[5-[2-(trifluoromethyl)pyrimidin-4-yl]-1h-pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyridine Chemical compound FC(F)(F)C1=NC=CC(C=2C(=CNN=2)C2=CN3N=CN=C3C=C2)=N1 DPICOUUHHUBYDI-UHFFFAOYSA-N 0.000 claims description 4
101150101604 ACVR1B gene Proteins 0.000 claims description 4
BTAJRCJWIJOGDV-UHFFFAOYSA-N [4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]piperidin-1-yl]-(3-chlorophenyl)methanone Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)C(=O)C=2C=C(Cl)C=CC=2)C=2C=C3OCOC3=CC=2)=N1 BTAJRCJWIJOGDV-UHFFFAOYSA-N 0.000 claims description 4
YSFRQMGFXGXWMD-UHFFFAOYSA-N methyl 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxylate Chemical compound N12C=C(C(=O)OC)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(N)=N1 YSFRQMGFXGXWMD-UHFFFAOYSA-N 0.000 claims description 4
XXIVJMVKDFQRIS-UHFFFAOYSA-N n-[1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-4-bicyclo[2.2.2]octanyl]methanesulfonamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)NS(C)(=O)=O)C=2C=C3OCOC3=CC=2)=N1 XXIVJMVKDFQRIS-UHFFFAOYSA-N 0.000 claims description 4
OFYLYPTVTMOCTB-UHFFFAOYSA-N n-[2-(6-methylpyridin-2-yl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl]propanamide Chemical compound N1=C2N=C(NC(=O)CC)C=CN2C(C=2N=C(SC)N=CC=2)=C1C1=CC=CC(C)=N1 OFYLYPTVTMOCTB-UHFFFAOYSA-N 0.000 claims description 4
AXAGAGTVHZOYQD-UHFFFAOYSA-N n-[2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl]-3-pyridin-3-ylpropanamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(NC(=O)CCC=4C=NC=CC=4)=NC3=N2)C=2N=C(N=CC=2)S(C)(=O)=O)=N1 AXAGAGTVHZOYQD-UHFFFAOYSA-N 0.000 claims description 4
VGLHRJFHJIIEGB-UHFFFAOYSA-N n-[2-[4-(1,3-benzodioxol-5-yl)-3-(6-methylpyridin-2-yl)pyrazol-1-yl]ethyl]methanesulfonamide Chemical compound CC1=CC=CC(C=2C(=CN(CCNS(C)(=O)=O)N=2)C=2C=C3OCOC3=CC=2)=N1 VGLHRJFHJIIEGB-UHFFFAOYSA-N 0.000 claims description 4
VPRBGKHSSMMFKG-UHFFFAOYSA-N n-[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]cyclohexyl]-1-phenylmethanesulfonamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCC(CC2)NS(=O)(=O)CC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 VPRBGKHSSMMFKG-UHFFFAOYSA-N 0.000 claims description 4
FPVNUKSAQKMDQL-UHFFFAOYSA-N n-[[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]cyclohexyl]methyl]butane-1-sulfonamide Chemical compound C1CC(CNS(=O)(=O)CCCC)CCC1C1=NC(C=2C=C3OCOC3=CC=2)=C(C=2N=C(C)C=CC=2)N1 FPVNUKSAQKMDQL-UHFFFAOYSA-N 0.000 claims description 4
XRQCPLADXMJECN-UHFFFAOYSA-N n-hydroxy-1-[4-(3-methyl-4-oxoquinazolin-6-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(=O)NO)C=2C=C3C(=O)N(C)C=NC3=CC=2)=N1 XRQCPLADXMJECN-UHFFFAOYSA-N 0.000 claims description 4
229940080818 propionamide Drugs 0.000 claims description 4
PCCZEQHMOCIYSN-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-[[3-(trifluoromethyl)phenyl]methylsulfonyl]piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound FC(F)(F)C1=CC=CC(CS(=O)(=O)N2CCC(CC2)C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)=C1 PCCZEQHMOCIYSN-UHFFFAOYSA-N 0.000 claims description 3
WMBVVXOGMONONM-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-[2-(dimethylamino)ethyl]-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound N12C=C(C(=O)NCCN(C)C)C=CC2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(N)=N1 WMBVVXOGMONONM-UHFFFAOYSA-N 0.000 claims description 3
IIVJQOJFWOXTLG-UHFFFAOYSA-N morpholin-4-yl-[5-(5-pyridin-2-yl-1h-pyrazol-4-yl)-1h-indazol-3-yl]methanone Chemical compound N=1NC2=CC=C(C=3C(=NNC=3)C=3N=CC=CC=3)C=C2C=1C(=O)N1CCOCC1 IIVJQOJFWOXTLG-UHFFFAOYSA-N 0.000 claims description 3
HNZSKMMZMZQUQM-UHFFFAOYSA-N n-[[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]cyclohexyl]methyl]propane-2-sulfonamide Chemical compound C1CC(CNS(=O)(=O)C(C)C)CCC1C1=NC(C=2C=C3OCOC3=CC=2)=C(C=2N=C(C)C=CC=2)N1 HNZSKMMZMZQUQM-UHFFFAOYSA-N 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
SBIXZUVKSKBIOQ-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(pyridin-4-ylmethylsulfonyl)piperidin-4-yl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)CC=2C=CN=CC=2)C=2C=C3OCOC3=CC=2)=N1 SBIXZUVKSKBIOQ-UHFFFAOYSA-N 0.000 claims description 2
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201000000054 Coronary Restenosis Diseases 0.000 claims description 2
206010056489 Coronary artery restenosis Diseases 0.000 claims description 2
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125000004356 hydroxy functional group Chemical group O* 0.000 claims 28
SVVCBKPGSAZAIZ-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-(1,4-dioxan-2-ylmethyl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C(=O)NCC2OCCOC2)C=2N=C(N)N=CC=2)=N1 SVVCBKPGSAZAIZ-UHFFFAOYSA-N 0.000 claims 8
VXTGVZRNWICVJF-UHFFFAOYSA-N n-[3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyrimidin-7-yl]acetamide Chemical compound N1=C2N=C(NC(=O)C)C=CN2C(C=2N=C(N)N=CC=2)=C1C1=CC=CC(C)=N1 VXTGVZRNWICVJF-UHFFFAOYSA-N 0.000 claims 8
RGNMSMJXVJXJIK-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-(3-imidazol-1-ylpropyl)bicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(=O)NCCCN2C=NC=C2)C=2C=C3OCOC3=CC=2)=N1 RGNMSMJXVJXJIK-UHFFFAOYSA-N 0.000 claims 4
ZRTGIBNKIAKGJK-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-[(3-chloro-4-fluorophenyl)methyl]bicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(=O)NCC=2C=C(Cl)C(F)=CC=2)C=2C=C3OCOC3=CC=2)=N1 ZRTGIBNKIAKGJK-UHFFFAOYSA-N 0.000 claims 4
SXNCKMDMFDMHGZ-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-butylbicyclo[2.2.2]octane-4-carboxamide Chemical compound C1CC(C(=O)NCCCC)(CC2)CCC12C(N1)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CC(C)=N1 SXNCKMDMFDMHGZ-UHFFFAOYSA-N 0.000 claims 4
XZZCGMDSLJGNSF-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-ethylbicyclo[2.2.2]octane-4-carboxamide Chemical compound C1CC(C(=O)NCC)(CC2)CCC12C(N1)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CC(C)=N1 XZZCGMDSLJGNSF-UHFFFAOYSA-N 0.000 claims 4
HDYXSERXYSWHPR-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-methylbicyclo[2.2.2]octane-4-carboxamide Chemical compound C1CC(C(=O)NC)(CC2)CCC12C(N1)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CC(C)=N1 HDYXSERXYSWHPR-UHFFFAOYSA-N 0.000 claims 4
CFAJOGKZNGBSHP-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-propan-2-ylbicyclo[2.2.2]octane-4-carboxamide Chemical compound C1CC(C(=O)NC(C)C)(CC2)CCC12C(N1)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CC(C)=N1 CFAJOGKZNGBSHP-UHFFFAOYSA-N 0.000 claims 4
XEDYDXQBBLLNLV-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octan-4-ol Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(O)(CC2)CC3)C=2C=C3OCOC3=CC=2)=N1 XEDYDXQBBLLNLV-UHFFFAOYSA-N 0.000 claims 4
JUHTXZGCTPDXRU-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(N)=O)C=2C=C3OCOC3=CC=2)=N1 JUHTXZGCTPDXRU-UHFFFAOYSA-N 0.000 claims 4
LZAPLGQNLFUTOU-UHFFFAOYSA-N 1-[4-quinoxalin-6-yl-5-[2-(trifluoromethyl)pyrimidin-4-yl]-1h-imidazol-2-yl]bicyclo[2.2.2]octan-4-ol Chemical compound C1CC(O)(CC2)CCC12C(N1)=NC(C=2C=C3N=CC=NC3=CC=2)=C1C1=CC=NC(C(F)(F)F)=N1 LZAPLGQNLFUTOU-UHFFFAOYSA-N 0.000 claims 4
NHBUNMRREKYNKL-UHFFFAOYSA-N 1-[5-(2-cyclopropylpyrimidin-4-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]bicyclo[2.2.2]octan-4-ol Chemical compound C1CC(O)(CC2)CCC12C(N1)=NC(C=2C=C3N=CC=NC3=CC=2)=C1C(N=1)=CC=NC=1C1CC1 NHBUNMRREKYNKL-UHFFFAOYSA-N 0.000 claims 4
HBTUBFWKPRCCGB-UHFFFAOYSA-N 1-[5-(6-methylpyridin-2-yl)-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(NC(=N2)C23CCC(CC2)(CC3)C(N)=O)C2=CN3N=CN=C3C=C2)=N1 HBTUBFWKPRCCGB-UHFFFAOYSA-N 0.000 claims 4
VFTPRXRFTGGRMR-UHFFFAOYSA-N 1-[5-[2-(cyclopropylamino)pyrimidin-4-yl]-4-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-hydroxybicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(NC(=N2)C23CCC(CC2)(CC3)C(=O)NO)C=2N=C(NC3CC3)N=CC=2)=N1 VFTPRXRFTGGRMR-UHFFFAOYSA-N 0.000 claims 4
GNHRGEPQRGPMCT-UHFFFAOYSA-N 1-[5-[2-(cyclopropylamino)pyrimidin-4-yl]-4-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-methoxybicyclo[2.2.2]octane-4-carboxamide Chemical compound C1CC(C(=O)NOC)(CC2)CCC12C(N1)=NC(C=2N=C(C)C=CC=2)=C1C(N=1)=CC=NC=1NC1CC1 GNHRGEPQRGPMCT-UHFFFAOYSA-N 0.000 claims 4
BFTOGZFVFWSNJF-UHFFFAOYSA-N 1-[5-[2-(cyclopropylamino)pyrimidin-4-yl]-4-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(NC(=N2)C23CCC(CC2)(CC3)C(N)=O)C=2N=C(NC3CC3)N=CC=2)=N1 BFTOGZFVFWSNJF-UHFFFAOYSA-N 0.000 claims 4
MZJSZQWWQZFBNG-UHFFFAOYSA-N 2,2,2-trifluoro-n-[4-[5-(6-methylpyridin-2-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]cyclohexyl]acetamide Chemical compound CC1=CC=CC(C2=C(NC(=N2)C2CCC(CC2)NC(=O)C(F)(F)F)C=2C=C3N=CC=NC3=CC=2)=N1 MZJSZQWWQZFBNG-UHFFFAOYSA-N 0.000 claims 4
ZXZQBJLOMCZQHF-UHFFFAOYSA-N 2-(6-methylpyridin-2-yl)-3-(2-pyrrolidin-1-ylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(N=CC=2)N2CCCC2)=N1 ZXZQBJLOMCZQHF-UHFFFAOYSA-N 0.000 claims 4
OYBDBJISEUFIPR-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-1h-pyrazol-5-yl]pyridine Chemical compound C1=C2OCOC2=CC=C1C1=CNN=C1C1=CC=CC=N1 OYBDBJISEUFIPR-UHFFFAOYSA-N 0.000 claims 4
HXKYYFMLJPHFTP-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-benzylsulfonylpiperidin-3-yl)-1h-imidazol-5-yl]pyridine Chemical compound C1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CN1S(=O)(=O)CC1=CC=CC=C1 HXKYYFMLJPHFTP-UHFFFAOYSA-N 0.000 claims 4
RDGCFSQXZFOYHX-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-benzylsulfonylpiperidin-4-yl)-1h-imidazol-5-yl]-6-ethylpyridine Chemical compound CCC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)CC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 RDGCFSQXZFOYHX-UHFFFAOYSA-N 0.000 claims 4
NLYMASABUDSJAK-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-benzylsulfonylpiperidin-4-yl)-1h-imidazol-5-yl]pyridine Chemical compound C1CC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CCN1S(=O)(=O)CC1=CC=CC=C1 NLYMASABUDSJAK-UHFFFAOYSA-N 0.000 claims 4
HGSNZSXZNFRRKD-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(2-phenylethylsulfonyl)piperidin-4-yl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)CCC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 HGSNZSXZNFRRKD-UHFFFAOYSA-N 0.000 claims 4
KXWFPORIVJKXPN-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(4-phenylphenyl)sulfonylpiperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1S(=O)(=O)N(CC1)CCC1C(N1)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CC=N1 KXWFPORIVJKXPN-UHFFFAOYSA-N 0.000 claims 4
JMYMOBAFZUSNHT-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(furan-2-yl)-2-methylpiperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound CC1CC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CCN1C1=CC=CO1 JMYMOBAFZUSNHT-UHFFFAOYSA-N 0.000 claims 4
OPLIBFMPIBWMKJ-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(pyridin-3-ylmethylsulfonyl)piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C1CC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CCN1S(=O)(=O)CC1=CC=CN=C1 OPLIBFMPIBWMKJ-UHFFFAOYSA-N 0.000 claims 4
KWYXWHJTVNXDNG-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(pyridin-4-ylmethylsulfonyl)piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C1CC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CCN1S(=O)(=O)CC1=CC=NC=C1 KWYXWHJTVNXDNG-UHFFFAOYSA-N 0.000 claims 4
GRYJBXNBDAWYNI-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-[(2-nitrophenyl)methylsulfonyl]piperidin-4-yl]-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)CC=2C(=CC=CC=2)[N+]([O-])=O)C=2C=C3OCOC3=CC=2)=N1 GRYJBXNBDAWYNI-UHFFFAOYSA-N 0.000 claims 4
XCFZTCGAQOLULN-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-[(4-fluorophenyl)methylsulfonyl]piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C1=CC(F)=CC=C1CS(=O)(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 XCFZTCGAQOLULN-UHFFFAOYSA-N 0.000 claims 4
CFNZVCJCUGTYBR-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-[(4-methylphenyl)methylsulfonyl]piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C1=CC(C)=CC=C1CS(=O)(=O)N1CCC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CC1 CFNZVCJCUGTYBR-UHFFFAOYSA-N 0.000 claims 4
OVTSOLBWYPDIHT-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-[(4-phenylphenyl)methylsulfonyl]piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C1CC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CCN1S(=O)(=O)CC(C=C1)=CC=C1C1=CC=CC=C1 OVTSOLBWYPDIHT-UHFFFAOYSA-N 0.000 claims 4
ATYHAOKWLVQUSW-UHFFFAOYSA-N 2-[4-(2,3-dihydro-1,4-benzodioxin-6-yl)-1h-pyrazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C=2C(=CNN=2)C=2C=C3OCCOC3=CC=2)=N1 ATYHAOKWLVQUSW-UHFFFAOYSA-N 0.000 claims 4
IHUYHJOWTKRENW-UHFFFAOYSA-N 2-[[4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]piperidin-1-yl]sulfonylmethyl]pyridine Chemical compound C1CC(C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=CC=CC=2)CCN1S(=O)(=O)CC1=CC=CC=N1 IHUYHJOWTKRENW-UHFFFAOYSA-N 0.000 claims 4
VZJCYHQIJKTKCJ-UHFFFAOYSA-N 3,6-dichloro-4-[4-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]butylcarbamoyl]-2-(2,4,5,7-tetrachloro-3-hydroxy-6-oxo-8a,9-dihydroxanthen-9-yl)benzoic acid Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCCNC(=O)C=3C(=C(C4C5=CC(Cl)=C(O)C(Cl)=C5OC5=C(Cl)C(=O)C(Cl)=CC54)C(C(O)=O)=C(Cl)C=3)Cl)N=CC=2)=N1 VZJCYHQIJKTKCJ-UHFFFAOYSA-N 0.000 claims 4
VDVOBHGYLRGHPS-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)-n-(2-thiophen-2-ylethyl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C(=O)NCCC=2SC=CC=2)C=2N=C(N)N=CC=2)=N1 VDVOBHGYLRGHPS-UHFFFAOYSA-N 0.000 claims 4
YUPNYCFIICXNPO-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)-n-methylsulfonylimidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NS(C)(=O)=O)C=2N=C(N)N=CC=2)=N1 YUPNYCFIICXNPO-UHFFFAOYSA-N 0.000 claims 4
CLIRYVSLRLIRFS-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=C(C=CC3=N2)C(N)=O)C=2N=C(N)N=CC=2)=N1 CLIRYVSLRLIRFS-UHFFFAOYSA-N 0.000 claims 4
QNKDCPDOULOXBJ-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-(2-hydroxyethyl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NCCO)C=2N=C(N)N=CC=2)=N1 QNKDCPDOULOXBJ-UHFFFAOYSA-N 0.000 claims 4
IHBLACKKNNTMNA-UHFFFAOYSA-N 3-(2-aminopyrimidin-4-yl)-n-[3-(4-methylpiperazin-1-yl)propyl]-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-6-carboxamide Chemical compound C1CN(C)CCN1CCCNC(=O)C1=CN2C(C=3N=C(N)N=CC=3)=C(C=3N=C(C)C=CC=3)N=C2C=C1 IHBLACKKNNTMNA-UHFFFAOYSA-N 0.000 claims 4
NKZVQBJACLKGJT-UHFFFAOYSA-N 3-[2-(4-methylpiperazin-1-yl)pyrimidin-4-yl]-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine Chemical compound C1CN(C)CCN1C1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 NKZVQBJACLKGJT-UHFFFAOYSA-N 0.000 claims 4
XAZXLZNLGFUKFB-UHFFFAOYSA-N 3-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]phenol Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NC=3C=C(O)C=CC=3)N=CC=2)=N1 XAZXLZNLGFUKFB-UHFFFAOYSA-N 0.000 claims 4
AGSSPIXIGIFOKP-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)-7-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(F)(F)F)C=2N=C(N)N=CC=2)=N1 AGSSPIXIGIFOKP-UHFFFAOYSA-N 0.000 claims 4
RMHURWLBIXLSDK-UHFFFAOYSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-(1h-pyrazol-5-yl)pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NC=3NN=CC=3)N=CC=2)=N1 RMHURWLBIXLSDK-UHFFFAOYSA-N 0.000 claims 4
VHVLKQPXJUKJFV-SFHVURJKSA-N 4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-n-[(1s)-1-phenylethyl]pyrimidin-2-amine Chemical compound N([C@@H](C)C=1C=CC=CC=1)C(N=1)=NC=CC=1C(N1C=CC=CC1=N1)=C1C1=CC=CC(C)=N1 VHVLKQPXJUKJFV-SFHVURJKSA-N 0.000 claims 4
MYKNCPCNCPKGDH-UHFFFAOYSA-N 4-[2-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]ethyl]benzenesulfonamide Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCC=3C=CC(=CC=3)S(N)(=O)=O)N=CC=2)=N1 MYKNCPCNCPKGDH-UHFFFAOYSA-N 0.000 claims 4
MSSYFOCCFPTMEM-UHFFFAOYSA-N 4-[4-[2-(6-methylpyridin-2-yl)pyrazolo[1,5-c]pyrimidin-3-yl]pyrimidin-2-yl]morpholine Chemical compound CC1=CC=CC(C=2C(=C3C=CN=CN3N=2)C=2N=C(N=CC=2)N2CCOCC2)=N1 MSSYFOCCFPTMEM-UHFFFAOYSA-N 0.000 claims 4
DFMXDYMTTUZLHC-UHFFFAOYSA-N 4-[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]piperidin-1-yl]sulfonyl-5-methyl-1,2-oxazole Chemical compound O1N=CC(S(=O)(=O)N2CCC(CC2)C=2NC(=C(N=2)C=2C=C3OCOC3=CC=2)C=2N=C(C)C=CC=2)=C1C DFMXDYMTTUZLHC-UHFFFAOYSA-N 0.000 claims 4
QVXCQUWCCGYXPM-UHFFFAOYSA-N 4-[7-(aminomethyl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound CC1=CC=CC(C2=C(N3C=CC(CN)=CC3=N2)C=2N=C(N)N=CC=2)=N1 QVXCQUWCCGYXPM-UHFFFAOYSA-N 0.000 claims 4
HPUFRDPDKQBLDH-UHFFFAOYSA-N 4-propan-2-yloxy-6-(5-pyridin-2-yl-1h-pyrazol-4-yl)quinazoline Chemical compound C1=C2C(OC(C)C)=NC=NC2=CC=C1C1=CNN=C1C1=CC=CC=N1 HPUFRDPDKQBLDH-UHFFFAOYSA-N 0.000 claims 4
ZLZCRVQDMUKNHC-UHFFFAOYSA-N 5-(dimethylamino)-n-[4-[[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]amino]butyl]naphthalene-1-sulfonamide Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)NCCCCNC(N=1)=NC=CC=1C(N1C=CC=CC1=N1)=C1C1=CC=CC(C)=N1 ZLZCRVQDMUKNHC-UHFFFAOYSA-N 0.000 claims 4
OREILLURMWYPQE-UHFFFAOYSA-N 6-(5-pyridin-2-yl-1h-pyrazol-4-yl)-4h-1,4-benzoxazin-3-one Chemical compound C1=C2NC(=O)COC2=CC=C1C1=CNN=C1C1=CC=CC=N1 OREILLURMWYPQE-UHFFFAOYSA-N 0.000 claims 4
COOYKNZJWSGUJD-UHFFFAOYSA-N 6-[5-(2-cyclopropylpyrimidin-4-yl)-2-(1-methylsulfonylpiperidin-4-yl)-1h-imidazol-4-yl]quinoxaline Chemical compound C1CN(S(=O)(=O)C)CCC1C1=NC(C=2C=C3N=CC=NC3=CC=2)=C(C=2N=C(N=CC=2)C2CC2)N1 COOYKNZJWSGUJD-UHFFFAOYSA-N 0.000 claims 4
PHIYKABHHHBNIA-UHFFFAOYSA-N 6-[5-(6-methylpyridin-2-yl)-1h-pyrazol-4-yl]quinoline Chemical compound CC1=CC=CC(C=2C(=CNN=2)C=2C=C3C=CC=NC3=CC=2)=N1 PHIYKABHHHBNIA-UHFFFAOYSA-N 0.000 claims 4
VXJLYXCHOKEODY-UHFFFAOYSA-N 6-[5-(6-methylpyridin-2-yl)-1h-pyrazol-4-yl]quinoxaline Chemical compound CC1=CC=CC(C=2C(=CNN=2)C=2C=C3N=CC=NC3=CC=2)=N1 VXJLYXCHOKEODY-UHFFFAOYSA-N 0.000 claims 4
TYUINBRGEGXQGY-UHFFFAOYSA-N 6-[6-methyl-2-(6-methylpyridin-2-yl)-8-(2-pyridin-4-ylethylamino)imidazo[1,2-a]pyridin-3-yl]-1h-pyrimidin-2-one Chemical compound C12=NC(C=3N=C(C)C=CC=3)=C(C=3N=C(O)N=CC=3)N2C=C(C)C=C1NCCC1=CC=NC=C1 TYUINBRGEGXQGY-UHFFFAOYSA-N 0.000 claims 4
WHIRSMPBKKWVNL-UHFFFAOYSA-N 6-[8-bromo-6-methyl-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]-1h-pyrimidin-2-one Chemical compound N12C=C(C)C=C(Br)C2=NC(C=2N=C(C)C=CC=2)=C1C1=CC=NC(O)=N1 WHIRSMPBKKWVNL-UHFFFAOYSA-N 0.000 claims 4
VIRLLLRMQBHWCT-UHFFFAOYSA-N 6-chloro-2-(6-methylpyridin-2-yl)-3-(2-methylsulfonylpyrimidin-4-yl)imidazo[1,2-a]pyridine Chemical compound CC1=CC=CC(C2=C(N3C=C(Cl)C=CC3=N2)C=2N=C(N=CC=2)S(C)(=O)=O)=N1 VIRLLLRMQBHWCT-UHFFFAOYSA-N 0.000 claims 4
VQLOYGTZJBJXHP-UHFFFAOYSA-N [1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-4-bicyclo[2.2.2]octanyl]-pyrrolidin-1-ylmethanone Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(=O)N2CCCC2)C=2C=C3OCOC3=CC=2)=N1 VQLOYGTZJBJXHP-UHFFFAOYSA-N 0.000 claims 4
JMDJSUXTQIQLKM-UHFFFAOYSA-N [4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]piperidin-1-yl]-(4-fluorophenyl)methanone Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)C(=O)C=2C=CC(F)=CC=2)C=2C=C3OCOC3=CC=2)=N1 JMDJSUXTQIQLKM-UHFFFAOYSA-N 0.000 claims 4
IJHGFKLYZUZFRU-UHFFFAOYSA-N benzyl 4-[4-(1,3-benzodioxol-5-yl)-5-(6-bromopyridin-2-yl)-1h-imidazol-2-yl]piperidine-1-carboxylate Chemical compound BrC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)C(=O)OCC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 IJHGFKLYZUZFRU-UHFFFAOYSA-N 0.000 claims 4
ITILYPBCIWETKV-UHFFFAOYSA-N benzyl 4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]piperidine-1-carboxylate Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)C(=O)OCC=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 ITILYPBCIWETKV-UHFFFAOYSA-N 0.000 claims 4
FTKRHDBAUOEGGQ-UHFFFAOYSA-N benzyl 4-[4-quinoxalin-6-yl-5-[2-(trifluoromethyl)pyrimidin-4-yl]-1h-imidazol-2-yl]piperidine-1-carboxylate Chemical compound FC(F)(F)C1=NC=CC(C2=C(N=C(N2)C2CCN(CC2)C(=O)OCC=2C=CC=CC=2)C=2C=C3N=CC=NC3=CC=2)=N1 FTKRHDBAUOEGGQ-UHFFFAOYSA-N 0.000 claims 4
229940098779 methanesulfonic acid Drugs 0.000 claims 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N methanesulfonic acid Substances CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 4
DFMWOFQKSBDAJT-UHFFFAOYSA-N methyl 1-[5-(6-methylpyridin-2-yl)-4-([1,2,4]triazolo[1,5-a]pyridin-6-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxylate Chemical compound C1CC(C(=O)OC)(CC2)CCC12C(N1)=NC(C2=CN3N=CN=C3C=C2)=C1C1=CC=CC(C)=N1 DFMWOFQKSBDAJT-UHFFFAOYSA-N 0.000 claims 4
OYNAFVDEMSUPFN-UHFFFAOYSA-N n'-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]butane-1,4-diamine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCCN)N=CC=2)=N1 OYNAFVDEMSUPFN-UHFFFAOYSA-N 0.000 claims 4
OXHZBUYAJNKADR-UHFFFAOYSA-N n'-[4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-yl]propane-1,3-diamine Chemical compound CC1=CC=CC(C2=C(N3C=CC=CC3=N2)C=2N=C(NCCCN)N=CC=2)=N1 OXHZBUYAJNKADR-UHFFFAOYSA-N 0.000 claims 4
VKJINYHQKFWPDV-UHFFFAOYSA-N n-(2-aminoethyl)-3-(2-aminopyrimidin-4-yl)-2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridine-7-carboxamide Chemical compound CC1=CC=CC(C2=C(N3C=CC(=CC3=N2)C(=O)NCCN)C=2N=C(N)N=CC=2)=N1 VKJINYHQKFWPDV-UHFFFAOYSA-N 0.000 claims 4
DPYZUMFTTWFGPP-UHFFFAOYSA-N n-(benzenesulfonyl)-1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-4-carboxamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C(=O)NS(=O)(=O)C=2C=CC=CC=2)C=2C=C3OCOC3=CC=2)=N1 DPYZUMFTTWFGPP-UHFFFAOYSA-N 0.000 claims 4
CERYWFBSRQOQIA-UHFFFAOYSA-N n-[(4-methoxyphenyl)methyl]-4-[2-(6-methylpyridin-2-yl)imidazo[1,2-a]pyridin-3-yl]pyrimidin-2-amine Chemical compound C1=CC(OC)=CC=C1CNC1=NC=CC(C=2N3C=CC=CC3=NC=2C=2N=C(C)C=CC=2)=N1 CERYWFBSRQOQIA-UHFFFAOYSA-N 0.000 claims 4
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