ZA200407902B - Tri-substituted hetreroaryls and methods of makingand using the same. - Google Patents

Tri-substituted hetreroaryls and methods of makingand using the same. Download PDF

Info

Publication number: ZA200407902B
Authority: ZA; South Africa
Prior art keywords: imidazol; methyl; pyridin; benzo; dioxol
Prior art date: 2002-04-04

Application number

ZA200407902A

Other languages

English (en)

Inventor

Wen-Cheng Lee

Feng Shan

Zhongli Zheng

Lihong Sun

Claudio Chuaqui

Russell C Petter

Original Assignee

Biogen Idec Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-04-04

Filing date

2004-09-30

Publication date

2005-09-22

2004-09-30 Application filed by Biogen Idec Inc filed Critical Biogen Idec Inc

2005-09-22 Publication of ZA200407902B publication Critical patent/ZA200407902B/en

Links

238000000034 method Methods 0.000 title claims description 44
150000001875 compounds Chemical class 0.000 claims description 91
125000000217 alkyl group Chemical group 0.000 claims description 46
239000000203 mixture Substances 0.000 claims description 45
-1 hydroxy, amino, nitro, oxo, thioxo Chemical group 0.000 claims description 43
125000001072 heteroaryl group Chemical group 0.000 claims description 31
102000009618 Transforming Growth Factors Human genes 0.000 claims description 29
125000003118 aryl group Chemical group 0.000 claims description 29
108010009583 Transforming Growth Factors Proteins 0.000 claims description 26
229910052739 hydrogen Inorganic materials 0.000 claims description 23
239000001257 hydrogen Substances 0.000 claims description 23
210000004027 cell Anatomy 0.000 claims description 20
230000002401 inhibitory effect Effects 0.000 claims description 17
150000002431 hydrogen Chemical group 0.000 claims description 16
230000003176 fibrotic effect Effects 0.000 claims description 15
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 15
238000004519 manufacturing process Methods 0.000 claims description 14
201000009030 Carcinoma Diseases 0.000 claims description 10
102000010834 Extracellular Matrix Proteins Human genes 0.000 claims description 10
108010037362 Extracellular Matrix Proteins Proteins 0.000 claims description 10
210000002744 extracellular matrix Anatomy 0.000 claims description 10
206010016654 Fibrosis Diseases 0.000 claims description 9
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 9
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
150000003839 salts Chemical class 0.000 claims description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 8
238000009825 accumulation Methods 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
GPRLTFBKWDERLU-UHFFFAOYSA-N bicyclo[2.2.2]octane Chemical group C1CC2CCC1CC2 GPRLTFBKWDERLU-UHFFFAOYSA-N 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
230000004761 fibrosis Effects 0.000 claims description 8
230000019491 signal transduction Effects 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
125000004193 piperazinyl group Chemical group 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
206010028980 Neoplasm Diseases 0.000 claims description 6
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000002877 alkyl aryl group Chemical group 0.000 claims description 6
125000003710 aryl alkyl group Chemical group 0.000 claims description 6
125000004475 heteroaralkyl group Chemical group 0.000 claims description 6
125000003386 piperidinyl group Chemical group 0.000 claims description 6
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 6
206010027476 Metastases Diseases 0.000 claims description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims description 5
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
230000009401 metastasis Effects 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
230000002018 overexpression Effects 0.000 claims description 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
208000005069 pulmonary fibrosis Diseases 0.000 claims description 5
210000004881 tumor cell Anatomy 0.000 claims description 5
KPUSZZFAYGWAHZ-UHFFFAOYSA-N 3-azabicyclo[2.2.2]octane Chemical group C1CC2CCC1NC2 KPUSZZFAYGWAHZ-UHFFFAOYSA-N 0.000 claims description 4
CJQNJRRDTPULTL-UHFFFAOYSA-N 3-azabicyclo[3.2.1]octane Chemical group C1C2CCC1CNC2 CJQNJRRDTPULTL-UHFFFAOYSA-N 0.000 claims description 4
CONVAEXWACQJSA-UHFFFAOYSA-N 3-oxabicyclo[2.2.2]octane Chemical group C1CC2CCC1OC2 CONVAEXWACQJSA-UHFFFAOYSA-N 0.000 claims description 4
206010004664 Biliary fibrosis Diseases 0.000 claims description 4
208000007342 Diabetic Nephropathies Diseases 0.000 claims description 4
208000007659 Fibroadenoma Diseases 0.000 claims description 4
201000008808 Fibrosarcoma Diseases 0.000 claims description 4
206010018364 Glomerulonephritis Diseases 0.000 claims description 4
206010019668 Hepatic fibrosis Diseases 0.000 claims description 4
206010020772 Hypertension Diseases 0.000 claims description 4
206010061216 Infarction Diseases 0.000 claims description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
206010039710 Scleroderma Diseases 0.000 claims description 4
206010046798 Uterine leiomyoma Diseases 0.000 claims description 4
125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 4
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
125000004104 aryloxy group Chemical group 0.000 claims description 4
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
LPCWKMYWISGVSK-UHFFFAOYSA-N bicyclo[3.2.1]octane Chemical group C1C2CCC1CCC2 LPCWKMYWISGVSK-UHFFFAOYSA-N 0.000 claims description 4
230000009787 cardiac fibrosis Effects 0.000 claims description 4
125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
208000033679 diabetic kidney disease Diseases 0.000 claims description 4
206010016629 fibroma Diseases 0.000 claims description 4
125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 4
208000017169 kidney disease Diseases 0.000 claims description 4
201000010260 leiomyoma Diseases 0.000 claims description 4
UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 claims description 4
230000002265 prevention Effects 0.000 claims description 4
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical group C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 claims description 4
201000002793 renal fibrosis Diseases 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
239000005711 Benzoic acid Substances 0.000 claims description 3
208000032612 Glial tumor Diseases 0.000 claims description 3
206010018338 Glioma Diseases 0.000 claims description 3
208000034578 Multiple myelomas Diseases 0.000 claims description 3
206010035226 Plasma cell myeloma Diseases 0.000 claims description 3
125000002252 acyl group Chemical group 0.000 claims description 3
125000003435 aroyl group Chemical group 0.000 claims description 3
210000003445 biliary tract Anatomy 0.000 claims description 3
210000000481 breast Anatomy 0.000 claims description 3
210000003679 cervix uteri Anatomy 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
125000004122 cyclic group Chemical group 0.000 claims description 3
125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
208000005017 glioblastoma Diseases 0.000 claims description 3
210000003128 head Anatomy 0.000 claims description 3
125000002883 imidazolyl group Chemical group 0.000 claims description 3
210000004185 liver Anatomy 0.000 claims description 3
210000004072 lung Anatomy 0.000 claims description 3
201000001441 melanoma Diseases 0.000 claims description 3
125000002950 monocyclic group Chemical group 0.000 claims description 3
210000003739 neck Anatomy 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
210000000496 pancreas Anatomy 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
210000002307 prostate Anatomy 0.000 claims description 3
230000011664 signaling Effects 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
150000001204 N-oxides Chemical class 0.000 claims description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 2
125000005018 aryl alkenyl group Chemical group 0.000 claims description 2
125000005163 aryl sulfanyl group Chemical group 0.000 claims description 2
125000005872 benzooxazolyl group Chemical group 0.000 claims description 2
125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 2
239000004202 carbamide Substances 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 2
125000005171 cycloalkylsulfanyl group Chemical group 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 2
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 2
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
229940098779 methanesulfonic acid Drugs 0.000 claims description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
125000003831 tetrazolyl group Chemical group 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
125000001425 triazolyl group Chemical group 0.000 claims description 2
239000000126 substance Substances 0.000 claims 40
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 24
125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims 10
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 7
125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims 7
230000037390 scarring Effects 0.000 claims 6
KSZCAGWHZCZJLZ-UHFFFAOYSA-N 1-methylimidazole-4-sulfonic acid Chemical compound CN1C=NC(S(O)(=O)=O)=C1 KSZCAGWHZCZJLZ-UHFFFAOYSA-N 0.000 claims 5
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 4
230000001404 mediated effect Effects 0.000 claims 4
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 3
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 3
201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 3
208000005777 Lupus Nephritis Diseases 0.000 claims 3
206010069351 acute lung injury Diseases 0.000 claims 3
PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 claims 3
238000002512 chemotherapy Methods 0.000 claims 3
208000036971 interstitial lung disease 2 Diseases 0.000 claims 3
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 3
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 3
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 3
OVOVWHQXIRPYJB-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]methanesulfonamide Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CNS(C)(=O)=O)(CC2)CC3)C=2C=C3OCOC3=CC=2)=N1 OVOVWHQXIRPYJB-UHFFFAOYSA-N 0.000 claims 3
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims 3
HNDXKIMMSFCCFW-UHFFFAOYSA-N propane-2-sulphonic acid Chemical compound CC(C)S(O)(=O)=O HNDXKIMMSFCCFW-UHFFFAOYSA-N 0.000 claims 3
238000001959 radiotherapy Methods 0.000 claims 3
208000037803 restenosis Diseases 0.000 claims 3
LRGLFIGRZTYOJU-UHFFFAOYSA-N thiophene-3-sulfonic acid Chemical compound OS(=O)(=O)C=1C=CSC=1 LRGLFIGRZTYOJU-UHFFFAOYSA-N 0.000 claims 3
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 2
KKVJMMSITMLWCO-UHFFFAOYSA-N 1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-n-(furan-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=2OC=CC=2)C=2C=C3OCOC3=CC=2)=N1 KKVJMMSITMLWCO-UHFFFAOYSA-N 0.000 claims 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 claims 2
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 2
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 2
BQRGKTFOVBEAPO-UHFFFAOYSA-N 4-[[4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]piperidin-1-yl]sulfonylmethyl]-7,7-dimethylbicyclo[2.2.1]heptan-3-one Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(=O)(=O)CC23C(CC(CC2)C3(C)C)=O)C=2C=C3OCOC3=CC=2)=N1 BQRGKTFOVBEAPO-UHFFFAOYSA-N 0.000 claims 2
CATSNJVOTSVZJV-UHFFFAOYSA-N Heptan-2-one Natural products CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 claims 2
VZDSAUHMBJSLFF-UHFFFAOYSA-N N-hydroxybicyclo[2.2.2]octane-1-carboxamide Chemical compound ONC(=O)C12CCC(CC1)CC2 VZDSAUHMBJSLFF-UHFFFAOYSA-N 0.000 claims 2
XPCUDTLFGOVKAW-UHFFFAOYSA-N [1-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]-4-bicyclo[2.2.2]octanyl] sulfamate Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)OS(N)(=O)=O)C=2C=C3OCOC3=CC=2)=N1 XPCUDTLFGOVKAW-UHFFFAOYSA-N 0.000 claims 2
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 2
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 2
ZXKINMCYCKHYFR-UHFFFAOYSA-N aminooxidanide Chemical compound [O-]N ZXKINMCYCKHYFR-UHFFFAOYSA-N 0.000 claims 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 claims 2
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
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 2
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 2
WDETXUVGXDZSND-UHFFFAOYSA-N n-[4-[5-(6-methylpyridin-2-yl)-4-quinoxalin-6-yl-1h-imidazol-2-yl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)C)CCC1C1=NC(C=2N=C(C)C=CC=2)=C(C=2C=C3N=CC=NC3=CC=2)N1 WDETXUVGXDZSND-UHFFFAOYSA-N 0.000 claims 2
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 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 2
BSXLLFUSNQCWJP-UHFFFAOYSA-N thiophene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CS1 BSXLLFUSNQCWJP-UHFFFAOYSA-N 0.000 claims 2
KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 claims 1
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 1
LQAUXDMGRBWDIU-UHFFFAOYSA-N (3-chloro-4-fluorophenyl)methanamine Chemical compound NCC1=CC=C(F)C(Cl)=C1 LQAUXDMGRBWDIU-UHFFFAOYSA-N 0.000 claims 1
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 1
HMTSWYPNXFHGEP-UHFFFAOYSA-N (4-methylphenyl)methanamine Chemical compound CC1=CC=C(CN)C=C1 HMTSWYPNXFHGEP-UHFFFAOYSA-N 0.000 claims 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
YCEVMAIOGXNBBQ-UHFFFAOYSA-N 1-[4-[4-(1,3-benzodioxol-5-yl)-5-pyridin-2-yl-1h-imidazol-2-yl]piperidin-1-yl]-2-methylpropan-2-ol Chemical compound C1CN(CC(C)(O)C)CCC1C1=NC(C=2C=C3OCOC3=CC=2)=C(C=2N=CC=CC=2)N1 YCEVMAIOGXNBBQ-UHFFFAOYSA-N 0.000 claims 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
PBQVYGAFMWMPQG-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-(1-methylsulfonylpiperidin-4-yl)-1h-imidazol-5-yl]-6-methylpyridine Chemical compound CC1=CC=CC(C2=C(N=C(N2)C2CCN(CC2)S(C)(=O)=O)C=2C=C3OCOC3=CC=2)=N1 PBQVYGAFMWMPQG-UHFFFAOYSA-N 0.000 claims 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
VONCCHSJBDBVLX-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(furan-2-ylmethyl)piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C=1C=COC=1CN(CC1)CCC1C(N1)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CC=N1 VONCCHSJBDBVLX-UHFFFAOYSA-N 0.000 claims 1
DJUINZOSOCXBAC-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-(pyridin-4-ylmethyl)piperidin-4-yl]-1h-imidazol-5-yl]pyridine Chemical compound C=1C=NC=CC=1CN(CC1)CCC1C(N1)=NC(C=2C=C3OCOC3=CC=2)=C1C1=CC=CC=N1 DJUINZOSOCXBAC-UHFFFAOYSA-N 0.000 claims 1
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 1
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 1
CVEXHODKIZBOMC-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-[(3,5-difluorophenyl)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(F)C=C(F)C=2)C=2C=C3OCOC3=CC=2)=N1 CVEXHODKIZBOMC-UHFFFAOYSA-N 0.000 claims 1
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 1
LRAVQICQOUSVKQ-UHFFFAOYSA-N 2-[4-(1,3-benzodioxol-5-yl)-2-[1-[(3-phenoxyphenyl)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(OC=3C=CC=CC=3)C=CC=2)C=2C=C3OCOC3=CC=2)=N1 LRAVQICQOUSVKQ-UHFFFAOYSA-N 0.000 claims 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 claims 1
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 1
GKODTPGEVLRHGQ-UHFFFAOYSA-N 4-[4-(1,3-benzodioxol-5-yl)-5-(6-methylpyridin-2-yl)-1h-imidazol-2-yl]bicyclo[2.2.2]octane-1-carbonitrile Chemical compound CC1=CC=CC(C2=C(N=C(N2)C23CCC(CC2)(CC3)C#N)C=2C=C3OCOC3=CC=2)=N1 GKODTPGEVLRHGQ-UHFFFAOYSA-N 0.000 claims 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
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 1
OEEBJKDZPLDBQI-UHFFFAOYSA-N 5,7-difluoro-1,3-benzothiazol-2-amine Chemical compound FC1=CC(F)=C2SC(N)=NC2=C1 OEEBJKDZPLDBQI-UHFFFAOYSA-N 0.000 claims 1
MAQAGRJURDEYDQ-UHFFFAOYSA-N 6-methylpyridine Chemical compound CC1=C=CC=C[N]1 MAQAGRJURDEYDQ-UHFFFAOYSA-N 0.000 claims 1
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims 1
GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 claims 1
JZHBNBRNRYSAKX-UHFFFAOYSA-N N-benzylbicyclo[2.2.2]octane-1-carboxamide Chemical compound C(C1=CC=CC=C1)NC(=O)C12CCC(CC1)CC2 JZHBNBRNRYSAKX-UHFFFAOYSA-N 0.000 claims 1
125000006383 alkylpyridyl group Chemical group 0.000 claims 1
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 1
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 1
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 1
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 1
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 1
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238000005805 hydroxylation reaction Methods 0.000 description 1
208000013403 hyperactivity Diseases 0.000 description 1
230000001506 immunosuppresive effect Effects 0.000 description 1
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238000002347 injection Methods 0.000 description 1
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229910052500 inorganic mineral Inorganic materials 0.000 description 1
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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210000004324 lymphatic system Anatomy 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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239000011707 mineral Substances 0.000 description 1
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210000004897 n-terminal region Anatomy 0.000 description 1
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239000007800 oxidant agent Substances 0.000 description 1
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FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
230000035515 penetration Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
229960004838 phosphoric acid Drugs 0.000 description 1
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230000003389 potentiating effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/08—Bridged systems

ZA200407902A 2002-04-04 2004-09-30 Tri-substituted hetreroaryls and methods of makingand using the same. ZA200407902B (en)

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US (1)	US7612094B2 (es)
EP (1)	EP1499308A4 (es)
JP (1)	JP2005527590A (es)
KR (1)	KR20040094908A (es)
CN (1)	CN100448868C (es)
AR (1)	AR039241A1 (es)
AU (1)	AU2003228446B2 (es)
CA (1)	CA2480860A1 (es)
EA (1)	EA010418B1 (es)
IL (1)	IL164295A0 (es)
IS (1)	IS7475A (es)
MX (1)	MXPA04009546A (es)
NO (1)	NO20044779L (es)
NZ (1)	NZ536202A (es)
PL (1)	PL373502A1 (es)
RS (1)	RS95904A (es)
UA (1)	UA81624C2 (es)
WO (1)	WO2003087304A2 (es)
ZA (1)	ZA200407902B (es)

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2003
- 2003-04-03 AR ARP030101166A patent/AR039241A1/es unknown
- 2003-04-04 WO PCT/US2003/010440 patent/WO2003087304A2/en active Application Filing
- 2003-04-04 NZ NZ536202A patent/NZ536202A/en not_active IP Right Cessation
- 2003-04-04 KR KR10-2004-7015706A patent/KR20040094908A/ko not_active Application Discontinuation
- 2003-04-04 UA UA20041108993A patent/UA81624C2/ru unknown
- 2003-04-04 US US10/510,459 patent/US7612094B2/en active Active
- 2003-04-04 JP JP2003584248A patent/JP2005527590A/ja active Pending
- 2003-04-04 CA CA002480860A patent/CA2480860A1/en not_active Abandoned
- 2003-04-04 CN CNB038126990A patent/CN100448868C/zh not_active Expired - Fee Related
- 2003-04-04 EP EP03726198A patent/EP1499308A4/en not_active Withdrawn
- 2003-04-04 AU AU2003228446A patent/AU2003228446B2/en not_active Ceased
- 2003-04-04 EA EA200401309A patent/EA010418B1/ru not_active IP Right Cessation
- 2003-04-04 RS YU95904A patent/RS95904A/sr unknown
- 2003-04-04 PL PL03373502A patent/PL373502A1/xx not_active Application Discontinuation
- 2003-04-04 MX MXPA04009546A patent/MXPA04009546A/es unknown
- 2003-04-04 IL IL16429503A patent/IL164295A0/xx unknown
2004
- 2004-09-28 IS IS7475A patent/IS7475A/is unknown
- 2004-09-30 ZA ZA200407902A patent/ZA200407902B/en unknown
- 2004-11-03 NO NO20044779A patent/NO20044779L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
CA2480860A1 (en)	2003-10-23
NZ536202A (en)	2009-08-28
IL164295A0 (en)	2005-12-18
MXPA04009546A (es)	2005-01-25
KR20040094908A (ko)	2004-11-10
EP1499308A4 (en)	2006-05-24
AR039241A1 (es)	2005-02-16
AU2003228446A1 (en)	2003-10-27
UA81624C2 (ru)	2008-01-25
IS7475A (is)	2004-09-28
CN1658866A (zh)	2005-08-24
EA010418B1 (ru)	2008-08-29
EA200401309A1 (ru)	2005-08-25
JP2005527590A (ja)	2005-09-15
US20060063809A1 (en)	2006-03-23
WO2003087304A2 (en)	2003-10-23
US7612094B2 (en)	2009-11-03
NO20044779L (no)	2005-01-04
AU2003228446B2 (en)	2009-08-06
PL373502A1 (en)	2005-09-05
CN100448868C (zh)	2009-01-07
WO2003087304A3 (en)	2004-07-22
EP1499308A2 (en)	2005-01-26
RS95904A (en)	2006-10-27

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