ZA200407902B - Tri-substituted hetreroaryls and methods of makingand using the same. - Google Patents
Tri-substituted hetreroaryls and methods of makingand using the same. Download PDFInfo
- Publication number
- ZA200407902B ZA200407902B ZA200407902A ZA200407902A ZA200407902B ZA 200407902 B ZA200407902 B ZA 200407902B ZA 200407902 A ZA200407902 A ZA 200407902A ZA 200407902 A ZA200407902 A ZA 200407902A ZA 200407902 B ZA200407902 B ZA 200407902B
- Authority
- ZA
- South Africa
- Prior art keywords
- imidazol
- methyl
- pyridin
- benzo
- dioxol
- Prior art date
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- 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
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- KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 claims 1
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- 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
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- 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
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- 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
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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
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- 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
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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
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- C—CHEMISTRY; METALLURGY
- 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
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- 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
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- 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
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
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- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Pulmonology (AREA)
- Gastroenterology & Hepatology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
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| US36979302P | 2002-04-04 | 2002-04-04 |
Publications (1)
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| EP (1) | EP1499308A4 (xx) |
| JP (1) | JP2005527590A (xx) |
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| CN (1) | CN100448868C (xx) |
| AR (1) | AR039241A1 (xx) |
| AU (1) | AU2003228446B2 (xx) |
| CA (1) | CA2480860A1 (xx) |
| EA (1) | EA010418B1 (xx) |
| IL (1) | IL164295A0 (xx) |
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| UA (1) | UA81624C2 (xx) |
| WO (1) | WO2003087304A2 (xx) |
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| GB0217787D0 (en) * | 2002-07-31 | 2002-09-11 | Glaxo Group Ltd | C ompounds |
| PL375973A1 (en) | 2002-09-18 | 2005-12-12 | Pfizer Products Inc. | Novel isothiazole and isoxazole compounds as transforming growth factor (tgf) inhibitors |
| JP2006502236A (ja) | 2002-09-18 | 2006-01-19 | ファイザー・プロダクツ・インク | 形質転換成長因子（ｔｇｆ）阻害剤としてのトリアゾール誘導体 |
| WO2004026306A2 (en) | 2002-09-18 | 2004-04-01 | Pfizer Products Inc. | Pyrazole derivatives as transforming growth factor (tgf) inhibitors |
| BR0314383A (pt) | 2002-09-18 | 2005-07-19 | Pfizer Prod Inc | Compostos de oxazol e tiazol como inibidores do fator de crescimento transformante(tgf) |
| EA200500378A1 (ru) * | 2002-09-18 | 2005-08-25 | Пфайзер Продактс Инк. | Новые соединения имидазола в качестве ингибиторов трансформирующего фактора роста (tgf) |
| PA8595001A1 (es) | 2003-03-04 | 2004-09-28 | Pfizer Prod Inc | Nuevos compuestos heteroaromaticos condensados que son inhibidores del factor de crecimiento transforante (tgf) |
| CN1921864A (zh) * | 2003-12-24 | 2007-02-28 | 西奥斯公司 | 使用TGF－β抑制剂治疗神经胶质瘤 |
| JP4853284B2 (ja) * | 2004-03-05 | 2012-01-11 | 大正製薬株式会社 | チアゾール誘導体 |
| US20080319012A1 (en) | 2004-04-21 | 2008-12-25 | In2Gen Co., Ltd. | 2-Pyridyl substituted imidazoles as ALK5 and/or ALK4 inhibitors |
| CA2578630A1 (en) * | 2004-08-31 | 2006-03-09 | Wen-Cherng Lee | Pyrimidinylimidazoles as tgf-beta inhibitors |
| WO2006028029A1 (ja) * | 2004-09-07 | 2006-03-16 | Sankyo Company, Limited | 置換ビフェニル誘導体 |
| CN101061116A (zh) | 2004-09-24 | 2007-10-24 | 詹森药业有限公司 | 磺酰胺化合物 |
| CA2584248A1 (en) * | 2004-10-15 | 2006-04-27 | Biogen Idec Ma Inc. | Methods of treating vascular injuries |
| GB0510141D0 (en) | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds B3 |
| EP1973914A2 (en) | 2005-12-22 | 2008-10-01 | Biogen Idec MA Inc. | Transforming growth factor modulators |
| US8642034B2 (en) | 2006-10-03 | 2014-02-04 | Genzyme Corporation | Use of TGF-β antagonists to treat infants at risk of developing bronchopulmonary dysplasia |
| WO2009009059A1 (en) * | 2007-07-09 | 2009-01-15 | Biogen Idec Ma Inc. | Spiro compounds as antagonists of tgf-beta |
| US8138168B1 (en) | 2007-09-26 | 2012-03-20 | Takeda Pharmaceutical Company Limited | Renin inhibitors |
| US8865732B2 (en) | 2008-03-21 | 2014-10-21 | Novartis Ag | Heterocyclic compounds and uses thereof |
| KR101408517B1 (ko) * | 2008-03-21 | 2014-06-17 | 노파르티스 아게 | 신규한 헤테로시클릭 화합물 및 그의 용도 |
| CL2009000904A1 (es) | 2008-04-21 | 2010-04-30 | Shionogi & Co | Compuestos derivados de ciclohexil sulfonamidas que tienen actividad antagonista en el receptor npy y5, composicion farmaceutica y formulacion farmaceutica que los comprende. |
| UA103319C2 (xx) | 2008-05-06 | 2013-10-10 | Глаксосмитклайн Ллк | Сполуки бензенсульфонамідтіазолу та -оксазолу$соединения бензенсульфонамидтиазола и -оксазола |
| CN102083439A (zh) * | 2008-05-30 | 2011-06-01 | 萨马保健系统有限责任公司 | 使用TGF-β受体抑制剂或活化素样激酶(ALK)5抑制剂A-83-01和SB-431542治疗眼病与伤口愈合症状的方法 |
| WO2010011917A1 (en) * | 2008-07-25 | 2010-01-28 | Glaxosmithkline Llc | SEH AND 11β-HSD1 DUAL INHIBITORS |
| CN102695511A (zh) * | 2009-04-17 | 2012-09-26 | 舒玛健康系统有限责任公司 | 抑制眼部瘢痕形成的转化生长因子-β受体抑制剂的用途 |
| USRE47141E1 (en) | 2010-06-29 | 2018-11-27 | EWHA University—Industry Collaboration Foundation | Methods of treating fibrosis, cancer and vascular injuries |
| US8080568B1 (en) * | 2010-06-29 | 2011-12-20 | Ewha University - Industry Collaboration Foundation | 2-pyridyl substituted imidazoles as therapeutic ALK5 and/or ALK4 inhibitors |
| US8513222B2 (en) | 2010-06-29 | 2013-08-20 | EWHA University—Industry Collaboration Foundation | Methods of treating fibrosis, cancer and vascular injuries |
| US8871744B2 (en) | 2010-07-21 | 2014-10-28 | B & G Partyers, LLC | Compounds and methods for selectively targeting tumor-associated mucins |
| RU2612958C2 (ru) | 2011-07-13 | 2017-03-14 | Ск Кемикалз Ко., Лтд. | 2-пиридилзамещенные имидазолы в качестве ингибиторов alk5 и/или alk4 |
| WO2013014262A1 (en) | 2011-07-27 | 2013-01-31 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Methods for diagnosing and treating myhre syndrome |
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| JP2023533849A (ja) | 2020-07-15 | 2023-08-04 | キエシ・フアルマチエウテイチ・ソチエタ・ペル・アチオニ | Ａｌｋ５阻害剤としてのピリダジニルアミノ誘導体 |
| AU2021307560A1 (en) | 2020-07-15 | 2023-02-23 | Chiesi Farmaceutici S.P.A. | Pyrido oxazine amino derivatives as ALK5 inhibitors |
| WO2022136221A1 (en) | 2020-12-23 | 2022-06-30 | Chiesi Farmaceutici S.P.A. | Pyrido oxazine derivatives as alk5 inhibitors |
| CN112759592A (zh) * | 2021-02-01 | 2021-05-07 | 无锡鸣鹭医药科技有限公司 | 一种6-碘[1,2,3]三唑并[1,5-a]吡啶的合成方法 |
| CN114105975A (zh) * | 2021-02-25 | 2022-03-01 | 无锡海伦生物科技有限公司 | 一种[1,2,4]三氮唑[1,5-a]吡啶-6-甲醛的合成方法 |
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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 EA EA200401309A patent/EA010418B1/ru not_active IP Right Cessation
- 2003-04-04 UA UA20041108993A patent/UA81624C2/ru unknown
- 2003-04-04 AU AU2003228446A patent/AU2003228446B2/en not_active Ceased
- 2003-04-04 JP JP2003584248A patent/JP2005527590A/ja active Pending
- 2003-04-04 KR KR10-2004-7015706A patent/KR20040094908A/ko not_active Application Discontinuation
- 2003-04-04 EP EP03726198A patent/EP1499308A4/en not_active Withdrawn
- 2003-04-04 US US10/510,459 patent/US7612094B2/en active Active
- 2003-04-04 RS YU95904A patent/RS95904A/sr unknown
- 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 MX MXPA04009546A patent/MXPA04009546A/es unknown
- 2003-04-04 IL IL16429503A patent/IL164295A0/xx unknown
- 2003-04-04 PL PL03373502A patent/PL373502A1/xx not_active Application Discontinuation
- 2003-04-04 NZ NZ536202A patent/NZ536202A/en not_active IP Right Cessation
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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 |
|---|---|
| AR039241A1 (es) | 2005-02-16 |
| IL164295A0 (en) | 2005-12-18 |
| RS95904A (xx) | 2006-10-27 |
| US7612094B2 (en) | 2009-11-03 |
| US20060063809A1 (en) | 2006-03-23 |
| UA81624C2 (ru) | 2008-01-25 |
| CA2480860A1 (en) | 2003-10-23 |
| CN1658866A (zh) | 2005-08-24 |
| EP1499308A2 (en) | 2005-01-26 |
| NZ536202A (en) | 2009-08-28 |
| JP2005527590A (ja) | 2005-09-15 |
| PL373502A1 (en) | 2005-09-05 |
| MXPA04009546A (es) | 2005-01-25 |
| EA010418B1 (ru) | 2008-08-29 |
| EA200401309A1 (ru) | 2005-08-25 |
| KR20040094908A (ko) | 2004-11-10 |
| NO20044779L (no) | 2005-01-04 |
| AU2003228446B2 (en) | 2009-08-06 |
| WO2003087304A2 (en) | 2003-10-23 |
| WO2003087304A3 (en) | 2004-07-22 |
| IS7475A (is) | 2004-09-28 |
| AU2003228446A1 (en) | 2003-10-27 |
| CN100448868C (zh) | 2009-01-07 |
| EP1499308A4 (en) | 2006-05-24 |
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