HRP20040504A2 - Sulfonamido substituted imidazopyridines - Google Patents
Sulfonamido substituted imidazopyridinesInfo
- Publication number
- HRP20040504A2 HRP20040504A2 HRP20040504A HRP20040504A2 HR P20040504 A2 HRP20040504 A2 HR P20040504A2 HR P20040504 A HRP20040504 A HR P20040504A HR P20040504 A2 HRP20040504 A2 HR P20040504A2
- Authority
- HR
- Croatia
- Prior art keywords
- imidazo
- pyridin
- amino
- ethoxymethyl
- butyl
- Prior art date
Links
- 150000005232 imidazopyridines Chemical class 0.000 title description 2
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 117
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 229910052799 carbon Inorganic materials 0.000 claims description 45
- -1 -alkyl-Y-alkenyl Chemical class 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 27
- 102000004127 Cytokines Human genes 0.000 claims description 26
- 108090000695 Cytokines Proteins 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 26
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 241001465754 Metazoa Species 0.000 claims description 19
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 17
- 230000015572 biosynthetic process Effects 0.000 claims description 16
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 13
- 230000006698 induction Effects 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 230000003612 virological effect Effects 0.000 claims description 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- HNQIVZYLYMDVSB-NJFSPNSNSA-N methanesulfonamide Chemical compound [14CH3]S(N)(=O)=O HNQIVZYLYMDVSB-NJFSPNSNSA-N 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 230000001613 neoplastic effect Effects 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- AOZMNNYIOVPNHJ-UHFFFAOYSA-N n-[3-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]propyl]methanesulfonamide Chemical compound N1=C(C)C(C)=C2N(CCCNS(C)(=O)=O)C(COCC)=NC2=C1N AOZMNNYIOVPNHJ-UHFFFAOYSA-N 0.000 claims description 4
- GNXMSXQEEFMDPJ-UHFFFAOYSA-N 2-(ethoxymethyl)-6,7-dimethyl-1-[2-(1-methylsulfonylpiperidin-4-yl)ethyl]imidazo[4,5-c]pyridin-4-amine Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC1CCN(S(C)(=O)=O)CC1 GNXMSXQEEFMDPJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 claims description 3
- OLKZFAZVUSSVGH-UHFFFAOYSA-N n-[4-(4-amino-2-butyl-6,7-dimethylimidazo[4,5-c]pyridin-1-yl)butyl]methanesulfonamide Chemical compound N1=C(C)C(C)=C2N(CCCCNS(C)(=O)=O)C(CCCC)=NC2=C1N OLKZFAZVUSSVGH-UHFFFAOYSA-N 0.000 claims description 3
- DGVFVEODKSWYJK-UHFFFAOYSA-N 1-[2-[1-[4-[[4-(dimethylamino)phenyl]diazenyl]phenyl]sulfonylpiperidin-4-yl]ethyl]-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-4-amine Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC(CC1)CCN1S(=O)(=O)C(C=C1)=CC=C1N=NC1=CC=C(N(C)C)C=C1 DGVFVEODKSWYJK-UHFFFAOYSA-N 0.000 claims description 2
- IBMXTGBEHBPGLC-UHFFFAOYSA-N 1-[4-(1,1-dioxo-1,2-thiazolidin-2-yl)butyl]-6,7-dimethyl-2-propylimidazo[4,5-c]pyridin-4-amine Chemical compound CCCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCCN1CCCS1(=O)=O IBMXTGBEHBPGLC-UHFFFAOYSA-N 0.000 claims description 2
- HESNGHFXTBCTNA-UHFFFAOYSA-N 4-[2-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]ethyl]-n,n-dimethylpiperidine-1-sulfonamide Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC1CCN(S(=O)(=O)N(C)C)CC1 HESNGHFXTBCTNA-UHFFFAOYSA-N 0.000 claims description 2
- WXPSOLDEAMAJPP-UHFFFAOYSA-N 4-amino-1-[4-(dimethylsulfamoylamino)butyl]-2-(ethoxymethyl)-7-methylimidazo[4,5-c]pyridine Chemical compound N1=CC(C)=C2N(CCCCNS(=O)(=O)N(C)C)C(COCC)=NC2=C1N WXPSOLDEAMAJPP-UHFFFAOYSA-N 0.000 claims description 2
- CCZSVQPAKLUELI-UHFFFAOYSA-N 4-amino-2-butyl-1-[4-(dimethylsulfamoylamino)butyl]-6,7-dimethylimidazo[4,5-c]pyridine Chemical compound N1=C(C)C(C)=C2N(CCCCNS(=O)(=O)N(C)C)C(CCCC)=NC2=C1N CCZSVQPAKLUELI-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- DYVTWANBKVYOQI-UHFFFAOYSA-N n-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]methanesulfonamide Chemical compound N1=C(C)C(C)=C2N(CCCNS(C)(=O)=O)C(C)=NC2=C1N DYVTWANBKVYOQI-UHFFFAOYSA-N 0.000 claims description 2
- OXJRPUMIQFPKIY-UHFFFAOYSA-N n-[4-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]butyl]methanesulfonamide Chemical compound N1=C(C)C(C)=C2N(CCCCNS(C)(=O)=O)C(COCC)=NC2=C1N OXJRPUMIQFPKIY-UHFFFAOYSA-N 0.000 claims description 2
- GVVGTARNSOAMIW-UHFFFAOYSA-N n-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butyl]methanesulfonamide Chemical compound N1=C(C)C=C2N(CCCCNS(C)(=O)=O)C(COCC)=NC2=C1N GVVGTARNSOAMIW-UHFFFAOYSA-N 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims description 2
- 229940124530 sulfonamide Drugs 0.000 claims description 2
- XLLFMFAAILQGBO-FMIVXFBMSA-N (e)-n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-2-phenylethenesulfonamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNS(=O)(=O)\C=C\C1=CC=CC=C1 XLLFMFAAILQGBO-FMIVXFBMSA-N 0.000 claims 1
- AYUINKIDLBLXIR-SDNWHVSQSA-N (e)-n-[3-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]propyl]-2-phenylethenesulfonamide Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNS(=O)(=O)\C=C\C1=CC=CC=C1 AYUINKIDLBLXIR-SDNWHVSQSA-N 0.000 claims 1
- ZQFVHILXTVZLDV-UHFFFAOYSA-N 1-[2-(1-butylsulfonylpiperidin-4-yl)ethyl]-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-4-amine Chemical compound C1CN(S(=O)(=O)CCCC)CCC1CCN1C2=C(C)C(C)=NC(N)=C2N=C1COCC ZQFVHILXTVZLDV-UHFFFAOYSA-N 0.000 claims 1
- BFCUTJOHOPUWGQ-UHFFFAOYSA-N 2-(ethoxymethyl)-1-[2-(1-ethylsulfonylpiperidin-4-yl)ethyl]-6,7-dimethylimidazo[4,5-c]pyridin-4-amine Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC1CCN(S(=O)(=O)CC)CC1 BFCUTJOHOPUWGQ-UHFFFAOYSA-N 0.000 claims 1
- VEXBNBISUFJIKZ-UHFFFAOYSA-N 2-(ethoxymethyl)-6,7-dimethyl-1-[2-(1-naphthalen-2-ylsulfonylpiperidin-4-yl)ethyl]imidazo[4,5-c]pyridin-4-amine Chemical compound C1=CC=CC2=CC(S(=O)(=O)N3CCC(CC3)CCN3C4=C(C)C(C)=NC(N)=C4N=C3COCC)=CC=C21 VEXBNBISUFJIKZ-UHFFFAOYSA-N 0.000 claims 1
- YQHJWQMJJQCVKL-UHFFFAOYSA-N 2-(ethoxymethyl)-6,7-dimethyl-1-[2-(1-propan-2-ylsulfonylpiperidin-4-yl)ethyl]imidazo[4,5-c]pyridin-4-amine Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC1CCN(S(=O)(=O)C(C)C)CC1 YQHJWQMJJQCVKL-UHFFFAOYSA-N 0.000 claims 1
- QNRLLBCZBABYEU-UHFFFAOYSA-N 2-(ethoxymethyl)-6,7-dimethyl-1-[2-[1-(4-methylsulfonylphenyl)sulfonylpiperidin-4-yl]ethyl]imidazo[4,5-c]pyridin-4-amine Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC(CC1)CCN1S(=O)(=O)C1=CC=C(S(C)(=O)=O)C=C1 QNRLLBCZBABYEU-UHFFFAOYSA-N 0.000 claims 1
- QHHRGOALWBPDRC-UHFFFAOYSA-N 2-(ethoxymethyl)-6,7-dimethyl-1-[2-[1-(4-phenylphenyl)sulfonylpiperidin-4-yl]ethyl]imidazo[4,5-c]pyridin-4-amine Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC(CC1)CCN1S(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 QHHRGOALWBPDRC-UHFFFAOYSA-N 0.000 claims 1
- LTWMKBUBTVKLJS-UHFFFAOYSA-N 2-(ethoxymethyl)-6,7-dimethyl-1-[2-[1-[4-(trifluoromethyl)phenyl]sulfonylpiperidin-4-yl]ethyl]imidazo[4,5-c]pyridin-4-amine Chemical compound CCOCC1=NC2=C(N)N=C(C)C(C)=C2N1CCC(CC1)CCN1S(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 LTWMKBUBTVKLJS-UHFFFAOYSA-N 0.000 claims 1
- BEHSXHFKMDXZOR-UHFFFAOYSA-N 4-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethylsulfamoyl]benzoic acid Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNS(=O)(=O)C1=CC=C(C(O)=O)C=C1 BEHSXHFKMDXZOR-UHFFFAOYSA-N 0.000 claims 1
- DIKNMAGLRNPLCD-UHFFFAOYSA-N 4-amino-1-[4-(dimethylsulfamoylamino)butyl]-6,7-dimethylimidazo[4,5-c]pyridine Chemical compound N1=C(C)C(C)=C2N(CCCCNS(=O)(=O)N(C)C)C=NC2=C1N DIKNMAGLRNPLCD-UHFFFAOYSA-N 0.000 claims 1
- YPWULWOOLXIYDQ-QNEJGDQOSA-N C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S(=O)(=O)NCCCCN2C3=C(C)C(C)=NC(N)=C3N=C2)C=C1 Chemical compound C1=CC(N(C)C)=CC=C1\N=N\C1=CC=C(S(=O)(=O)NCCCCN2C3=C(C)C(C)=NC(N)=C3N=C2)C=C1 YPWULWOOLXIYDQ-QNEJGDQOSA-N 0.000 claims 1
- QDJQMYUKUKPBHY-JEIPZWNWSA-N CCOCC1=NC2=C(N)N=C(C)C=C2N1CCCCNS(=O)(=O)C(C=C1)=CC=C1\N=N\C1=CC=C(N(C)C)C=C1 Chemical compound CCOCC1=NC2=C(N)N=C(C)C=C2N1CCCCNS(=O)(=O)C(C=C1)=CC=C1\N=N\C1=CC=C(N(C)C)C=C1 QDJQMYUKUKPBHY-JEIPZWNWSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- PMPGNVBILGZNKR-UHFFFAOYSA-N n-[1-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]-2-methylpropan-2-yl]methanesulfonamide Chemical compound N1=C(C)C(C)=C2N(CC(C)(C)NS(C)(=O)=O)C(COCC)=NC2=C1N PMPGNVBILGZNKR-UHFFFAOYSA-N 0.000 claims 1
- SZRXVUJCEOXNOU-UHFFFAOYSA-N n-[1-[4-amino-2-(ethoxymethyl)-6,7-dimethylimidazo[4,5-c]pyridin-1-yl]-2-methylpropan-2-yl]propane-2-sulfonamide Chemical compound N1=C(C)C(C)=C2N(CC(C)(C)NS(=O)(=O)C(C)C)C(COCC)=NC2=C1N SZRXVUJCEOXNOU-UHFFFAOYSA-N 0.000 claims 1
- FFNYVSPQBMNFSD-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-1-(2-nitrophenyl)methanesulfonamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNS(=O)(=O)CC1=CC=CC=C1[N+]([O-])=O FFNYVSPQBMNFSD-UHFFFAOYSA-N 0.000 claims 1
- CWRZRIVFNUEMEI-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-1-(7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonamide Chemical compound N1=C(C)C(C)=C2N(CCNS(=O)(=O)CC34C(CC(CC3)C4(C)C)=O)C(C)=NC2=C1N CWRZRIVFNUEMEI-UHFFFAOYSA-N 0.000 claims 1
- WABQHXXEEYRFFS-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-1-methylimidazole-4-sulfonamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNS(=O)(=O)C1=CN(C)C=N1 WABQHXXEEYRFFS-UHFFFAOYSA-N 0.000 claims 1
- OSOXBFCRCUBBEY-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-2,4-difluorobenzenesulfonamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNS(=O)(=O)C1=CC=C(F)C=C1F OSOXBFCRCUBBEY-UHFFFAOYSA-N 0.000 claims 1
- XRIYPXXGMFEJGD-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3,5-dimethyl-1,2-oxazole-4-sulfonamide Chemical compound CC1=NOC(C)=C1S(=O)(=O)NCCN1C2=C(C)C(C)=NC(N)=C2N=C1C XRIYPXXGMFEJGD-UHFFFAOYSA-N 0.000 claims 1
- RHDARXLPLTTWPE-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-cyanobenzenesulfonamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNS(=O)(=O)C1=CC=CC(C#N)=C1 RHDARXLPLTTWPE-UHFFFAOYSA-N 0.000 claims 1
- QHQNIVIUXKXEFI-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-3-fluorobenzenesulfonamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNS(=O)(=O)C1=CC=CC(F)=C1 QHQNIVIUXKXEFI-UHFFFAOYSA-N 0.000 claims 1
- SELJXCVUXVCRJB-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-4-(trifluoromethoxy)benzenesulfonamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNS(=O)(=O)C1=CC=C(OC(F)(F)F)C=C1 SELJXCVUXVCRJB-UHFFFAOYSA-N 0.000 claims 1
- CUNIXUWTBPBNCJ-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-4-(trifluoromethyl)benzenesulfonamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 CUNIXUWTBPBNCJ-UHFFFAOYSA-N 0.000 claims 1
- WQTJKIUMGBOIHW-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-4-cyanobenzenesulfonamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNS(=O)(=O)C1=CC=C(C#N)C=C1 WQTJKIUMGBOIHW-UHFFFAOYSA-N 0.000 claims 1
- RBFMOELWXHMFGN-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-4-methoxybenzenesulfonamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)NCCN1C2=C(C)C(C)=NC(N)=C2N=C1C RBFMOELWXHMFGN-UHFFFAOYSA-N 0.000 claims 1
- AMQISNMTOTWEGB-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-4-methylsulfonylbenzenesulfonamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNS(=O)(=O)C1=CC=C(S(C)(=O)=O)C=C1 AMQISNMTOTWEGB-UHFFFAOYSA-N 0.000 claims 1
- UWYXZBFTFOCGCT-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-4-phenylbenzenesulfonamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNS(=O)(=O)C(C=C1)=CC=C1C1=CC=CC=C1 UWYXZBFTFOCGCT-UHFFFAOYSA-N 0.000 claims 1
- XNVXGXRWEXOWLG-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]-5-chlorothiophene-2-sulfonamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNS(=O)(=O)C1=CC=C(Cl)S1 XNVXGXRWEXOWLG-UHFFFAOYSA-N 0.000 claims 1
- IHBYNMLOSYHLJJ-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]benzenesulfonamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNS(=O)(=O)C1=CC=CC=C1 IHBYNMLOSYHLJJ-UHFFFAOYSA-N 0.000 claims 1
- IQRIJRLKAATYNY-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]butane-1-sulfonamide Chemical compound N1=C(C)C(C)=C2N(CCNS(=O)(=O)CCCC)C(C)=NC2=C1N IQRIJRLKAATYNY-UHFFFAOYSA-N 0.000 claims 1
- PJSNKWBCIWHBCH-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]ethanesulfonamide Chemical compound N1=C(C)C(C)=C2N(CCNS(=O)(=O)CC)C(C)=NC2=C1N PJSNKWBCIWHBCH-UHFFFAOYSA-N 0.000 claims 1
- HRGCOYSKRWDVEN-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]naphthalene-1-sulfonamide Chemical compound C1=CC=C2C(S(=O)(=O)NCCN3C4=C(C)C(C)=NC(N)=C4N=C3C)=CC=CC2=C1 HRGCOYSKRWDVEN-UHFFFAOYSA-N 0.000 claims 1
- YPILHWLBRDFQPN-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]naphthalene-2-sulfonamide Chemical compound C1=CC=CC2=CC(S(=O)(=O)NCCN3C4=C(C)C(C)=NC(N)=C4N=C3C)=CC=C21 YPILHWLBRDFQPN-UHFFFAOYSA-N 0.000 claims 1
- PFWMIXCFNONSOZ-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]propane-2-sulfonamide Chemical compound N1=C(C)C(C)=C2N(CCNS(=O)(=O)C(C)C)C(C)=NC2=C1N PFWMIXCFNONSOZ-UHFFFAOYSA-N 0.000 claims 1
- ZZAQZZVHOYMVDF-UHFFFAOYSA-N n-[2-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)ethyl]thiophene-2-sulfonamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCNS(=O)(=O)C1=CC=CS1 ZZAQZZVHOYMVDF-UHFFFAOYSA-N 0.000 claims 1
- YYYYWJSFGFIADJ-UHFFFAOYSA-N n-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-1-(7,7-dimethyl-3-oxo-4-bicyclo[2.2.1]heptanyl)methanesulfonamide Chemical compound N1=C(C)C(C)=C2N(CCCNS(=O)(=O)CC34C(CC(CC3)C4(C)C)=O)C(C)=NC2=C1N YYYYWJSFGFIADJ-UHFFFAOYSA-N 0.000 claims 1
- NTHGPCKAQKTLFS-UHFFFAOYSA-N n-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-3-cyanobenzenesulfonamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNS(=O)(=O)C1=CC=CC(C#N)=C1 NTHGPCKAQKTLFS-UHFFFAOYSA-N 0.000 claims 1
- GUVQSOIOPJRLFW-UHFFFAOYSA-N n-[3-(4-amino-2,6,7-trimethylimidazo[4,5-c]pyridin-1-yl)propyl]-3-fluorobenzenesulfonamide Chemical compound CC1=NC2=C(N)N=C(C)C(C)=C2N1CCCNS(=O)(=O)C1=CC=CC(F)=C1 GUVQSOIOPJRLFW-UHFFFAOYSA-N 0.000 claims 1
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- XVSPCXFVTPUQGP-UHFFFAOYSA-N n-[4-[4-amino-2-(ethoxymethyl)-6-methylimidazo[4,5-c]pyridin-1-yl]butyl]-4-methylsulfonylbenzenesulfonamide Chemical compound CCOCC1=NC2=C(N)N=C(C)C=C2N1CCCCNS(=O)(=O)C1=CC=C(S(C)(=O)=O)C=C1 XVSPCXFVTPUQGP-UHFFFAOYSA-N 0.000 claims 1
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- FRYFHVSURUNGBE-UHFFFAOYSA-N n-[4-[4-amino-2-(ethoxymethyl)-7-methylimidazo[4,5-c]pyridin-1-yl]butyl]-3-fluorobenzenesulfonamide Chemical compound CCOCC1=NC2=C(N)N=CC(C)=C2N1CCCCNS(=O)(=O)C1=CC=CC(F)=C1 FRYFHVSURUNGBE-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
- 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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US10/016,073 US20020107262A1 (en) | 2000-12-08 | 2001-12-06 | Substituted imidazopyridines |
PCT/US2002/018220 WO2003050117A1 (en) | 2001-12-06 | 2002-06-07 | Sulfonamido substituted imidazopyridines |
Publications (1)
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HRP20040504A2 true HRP20040504A2 (en) | 2004-12-31 |
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HRP20040503 HRP20040503A2 (en) | 2001-12-06 | 2004-06-04 | Amide supstituted imidazopyridines |
HRP20040504 HRP20040504A2 (en) | 2001-12-06 | 2004-06-04 | Sulfonamido substituted imidazopyridines |
HRP20040506 HRP20040506A2 (en) | 2001-12-06 | 2004-06-04 | Urea substituted imidazopyridines |
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HRP20040503 HRP20040503A2 (en) | 2001-12-06 | 2004-06-04 | Amide supstituted imidazopyridines |
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HRP20040506 HRP20040506A2 (en) | 2001-12-06 | 2004-06-04 | Urea substituted imidazopyridines |
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US (1) | US20020107262A1 (es) |
EP (3) | EP1451186A2 (es) |
JP (3) | JP2005511745A (es) |
KR (3) | KR20040105695A (es) |
CN (4) | CN101220028A (es) |
AU (3) | AU2002315006B2 (es) |
BR (3) | BR0214749A (es) |
CA (3) | CA2468164A1 (es) |
HR (3) | HRP20040503A2 (es) |
IL (3) | IL161945A0 (es) |
MX (3) | MXPA04005331A (es) |
NO (3) | NO20042621L (es) |
NZ (3) | NZ532926A (es) |
PL (3) | PL370738A1 (es) |
RU (3) | RU2004117159A (es) |
UA (3) | UA77710C2 (es) |
WO (3) | WO2003050118A1 (es) |
ZA (3) | ZA200405337B (es) |
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2001
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2002
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