ZA200600424B - Bicyclic imidazol derivatives against flaviviridae - Google Patents
Bicyclic imidazol derivatives against flaviviridae Download PDFInfo
- Publication number
- ZA200600424B ZA200600424B ZA200600424A ZA200600424A ZA200600424B ZA 200600424 B ZA200600424 B ZA 200600424B ZA 200600424 A ZA200600424 A ZA 200600424A ZA 200600424 A ZA200600424 A ZA 200600424A ZA 200600424 B ZA200600424 B ZA 200600424B
- Authority
- ZA
- South Africa
- Prior art keywords
- substituted
- cyclohexyl
- quinolin
- benzoimidazole
- carboxylic acid
- Prior art date
Links
- -1 Bicyclic imidazol derivatives Chemical class 0.000 title claims description 278
- 241000710781 Flaviviridae Species 0.000 title claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 156
- 125000001072 heteroaryl group Chemical group 0.000 claims description 131
- 150000001875 compounds Chemical class 0.000 claims description 110
- 125000000217 alkyl group Chemical group 0.000 claims description 89
- 125000003118 aryl group Chemical group 0.000 claims description 69
- 125000003107 substituted aryl group Chemical group 0.000 claims description 64
- 125000000304 alkynyl group Chemical group 0.000 claims description 50
- 125000003342 alkenyl group Chemical group 0.000 claims description 49
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 46
- 239000001257 hydrogen Substances 0.000 claims description 46
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 40
- 150000002431 hydrogen Chemical class 0.000 claims description 31
- 229910052757 nitrogen Inorganic materials 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 18
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 18
- 241000711549 Hepacivirus C Species 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 14
- 241000700605 Viruses Species 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 11
- 102000006992 Interferon-alpha Human genes 0.000 claims description 9
- 108010047761 Interferon-alpha Proteins 0.000 claims description 9
- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 9
- 229960000329 ribavirin Drugs 0.000 claims description 9
- HZCAHMRRMINHDJ-DBRKOABJSA-N ribavirin Natural products O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1N=CN=C1 HZCAHMRRMINHDJ-DBRKOABJSA-N 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 208000005176 Hepatitis C Diseases 0.000 claims description 4
- 208000036142 Viral infection Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 230000009385 viral infection Effects 0.000 claims description 4
- 241000282414 Homo sapiens Species 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- 102000012479 Serine Proteases Human genes 0.000 claims description 2
- 108010022999 Serine Proteases Proteins 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 24
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 15
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 14
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 11
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims 10
- 125000004525 thiadiazinyl group Chemical group S1NN=C(C=C1)* 0.000 claims 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 9
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 claims 9
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 9
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 9
- 125000004607 1,2,3,4-tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 8
- 125000004242 cinnolin-3-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)N=NC2=C1[H] 0.000 claims 8
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 150000001412 amines Chemical class 0.000 claims 5
- 125000004104 aryloxy group Chemical group 0.000 claims 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 4
- 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 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 4
- IWUCXVSUMQZMFG-RGDLXGNYSA-N 1-[(2s,3s,4r,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,4-triazole-3-carboxamide Chemical compound N1=C(C(=O)N)N=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 IWUCXVSUMQZMFG-RGDLXGNYSA-N 0.000 claims 3
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims 3
- RHDYQUZYHZWTCI-UHFFFAOYSA-N 1-methoxy-4-phenylbenzene Chemical group C1=CC(OC)=CC=C1C1=CC=CC=C1 RHDYQUZYHZWTCI-UHFFFAOYSA-N 0.000 claims 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- JZFICWYCTCCINF-UHFFFAOYSA-N Thiadiazin Chemical compound S=C1SC(C)NC(C)N1CCN1C(=S)SC(C)NC1C JZFICWYCTCCINF-UHFFFAOYSA-N 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- YXVFYQXJAXKLAK-UHFFFAOYSA-N biphenyl-4-ol Chemical group C1=CC(O)=CC=C1C1=CC=CC=C1 YXVFYQXJAXKLAK-UHFFFAOYSA-N 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims 2
- 125000005505 thiomorpholino group Chemical group 0.000 claims 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- LPUCHTNHUHOTRY-UHFFFAOYSA-N 1-(3-bicyclo[2.2.1]heptanyl)ethanamine Chemical compound C1CC2C(C(N)C)CC1C2 LPUCHTNHUHOTRY-UHFFFAOYSA-N 0.000 claims 1
- BKEZCCOADKFOCR-UHFFFAOYSA-N 1-cyclohexyl-2-(2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzimidazole-5-carboxylic acid Chemical compound C=1C=C2NC(C)CCC2=CC=1C1=NC2=CC(C(O)=O)=CC=C2N1C1CCCCC1 BKEZCCOADKFOCR-UHFFFAOYSA-N 0.000 claims 1
- XLNFHFKMFYNZGY-UHFFFAOYSA-N 1-cyclohexyl-2-(2-methyl-1,4-dioxo-3h-phthalazin-6-yl)benzimidazole-5-carboxylic acid Chemical compound C=1C=C2C(=O)N(C)NC(=O)C2=CC=1C1=NC2=CC(C(O)=O)=CC=C2N1C1CCCCC1 XLNFHFKMFYNZGY-UHFFFAOYSA-N 0.000 claims 1
- NNCVVTDPHUUXOC-UHFFFAOYSA-N 1-cyclohexyl-2-(2-methyl-4-oxo-1h-quinolin-6-yl)benzimidazole-5-carboxylic acid Chemical compound C=1C=C2NC(C)=CC(=O)C2=CC=1C1=NC2=CC(C(O)=O)=CC=C2N1C1CCCCC1 NNCVVTDPHUUXOC-UHFFFAOYSA-N 0.000 claims 1
- LUZRJYOSQAUAJJ-UHFFFAOYSA-N 1-cyclohexyl-2-(2-methylpteridin-6-yl)benzimidazole-5-carboxylic acid Chemical compound C1=NC2=NC(C)=NC=C2N=C1C1=NC2=CC(C(O)=O)=CC=C2N1C1CCCCC1 LUZRJYOSQAUAJJ-UHFFFAOYSA-N 0.000 claims 1
- WTOJIUMTXUXGEW-UHFFFAOYSA-N 1-cyclohexyl-2-(2-methylquinazolin-7-yl)-n-methylsulfonylbenzimidazole-5-carboxamide Chemical compound C=1C2=NC(C)=NC=C2C=CC=1C1=NC2=CC(C(=O)NS(C)(=O)=O)=CC=C2N1C1CCCCC1 WTOJIUMTXUXGEW-UHFFFAOYSA-N 0.000 claims 1
- BFFWFDUCNNHBLM-UHFFFAOYSA-N 1-cyclohexyl-2-(2-naphthalen-1-ylquinolin-6-yl)benzimidazole-5-carboxylic acid Chemical compound C=1C=C2N=C(C=3C4=CC=CC=C4C=CC=3)C=CC2=CC=1C1=NC2=CC(C(=O)O)=CC=C2N1C1CCCCC1 BFFWFDUCNNHBLM-UHFFFAOYSA-N 0.000 claims 1
- YIGJZGQXEPUOHT-UHFFFAOYSA-N 1-cyclohexyl-2-(2-phenyl-1,2,3,4-tetrahydroquinolin-6-yl)benzimidazole-5-carboxylic acid Chemical compound C=1C=C2NC(C=3C=CC=CC=3)CCC2=CC=1C1=NC2=CC(C(=O)O)=CC=C2N1C1CCCCC1 YIGJZGQXEPUOHT-UHFFFAOYSA-N 0.000 claims 1
- BAXYSNSVMGVGTR-UHFFFAOYSA-N 1-cyclohexyl-2-(2-phenylpteridin-6-yl)benzimidazole-5-carboxylic acid Chemical compound C=1N=C2N=C(C=3C=CC=CC=3)N=CC2=NC=1C1=NC2=CC(C(=O)O)=CC=C2N1C1CCCCC1 BAXYSNSVMGVGTR-UHFFFAOYSA-N 0.000 claims 1
- XHUHIJYTJMRJSJ-UHFFFAOYSA-N 1-cyclohexyl-2-(2-pyridin-2-ylquinolin-6-yl)benzimidazole-5-carboxylic acid Chemical compound C=1C=C2N=C(C=3N=CC=CC=3)C=CC2=CC=1C1=NC2=CC(C(=O)O)=CC=C2N1C1CCCCC1 XHUHIJYTJMRJSJ-UHFFFAOYSA-N 0.000 claims 1
- VQCZWKZLWPOCKI-UHFFFAOYSA-N 1-cyclohexyl-2-(3-methyl-1,4-dihydroisoquinolin-6-yl)benzimidazole-5-carboxylic acid Chemical compound C1=C2CC(C)=NCC2=CC=C1C1=NC2=CC(C(O)=O)=CC=C2N1C1CCCCC1 VQCZWKZLWPOCKI-UHFFFAOYSA-N 0.000 claims 1
- WTKXMCRTGBWKCU-UHFFFAOYSA-N 1-cyclohexyl-2-(3-methylisoquinolin-6-yl)-n-methylsulfonylbenzimidazole-5-carboxamide Chemical compound C=1C=C2C=NC(C)=CC2=CC=1C1=NC2=CC(C(=O)NS(C)(=O)=O)=CC=C2N1C1CCCCC1 WTKXMCRTGBWKCU-UHFFFAOYSA-N 0.000 claims 1
- XMXHJRXCXZFBAK-UHFFFAOYSA-N 1-cyclohexyl-2-(3-phenylquinolin-6-yl)benzimidazole-5-carboxylic acid Chemical compound C=1C=C2N=CC(C=3C=CC=CC=3)=CC2=CC=1C1=NC2=CC(C(=O)O)=CC=C2N1C1CCCCC1 XMXHJRXCXZFBAK-UHFFFAOYSA-N 0.000 claims 1
- VBIVKJJOKUAQTJ-UHFFFAOYSA-N 1-cyclohexyl-2-(6-methyl-1,5-naphthyridin-2-yl)-n-methylsulfonylbenzimidazole-5-carboxamide Chemical compound C1=CC2=NC(C)=CC=C2N=C1C1=NC2=CC(C(=O)NS(C)(=O)=O)=CC=C2N1C1CCCCC1 VBIVKJJOKUAQTJ-UHFFFAOYSA-N 0.000 claims 1
- ADXKVUAMSDKDSD-UHFFFAOYSA-N 1-cyclohexyl-2-(6-methyl-1,5-naphthyridin-2-yl)benzimidazole-5-carboxylic acid Chemical compound C1=CC2=NC(C)=CC=C2N=C1C1=NC2=CC(C(O)=O)=CC=C2N1C1CCCCC1 ADXKVUAMSDKDSD-UHFFFAOYSA-N 0.000 claims 1
- RTPUZRAEDWZUCP-UHFFFAOYSA-N 1-cyclohexyl-2-(6-methyl-1,8-naphthyridin-3-yl)-n-methylsulfonylbenzimidazole-5-carboxamide Chemical compound C=1C2=CC(C)=CN=C2N=CC=1C1=NC2=CC(C(=O)NS(C)(=O)=O)=CC=C2N1C1CCCCC1 RTPUZRAEDWZUCP-UHFFFAOYSA-N 0.000 claims 1
- DKEFQEQWTNDNNV-UHFFFAOYSA-N 1-cyclohexyl-2-(6-methyl-1,8-naphthyridin-3-yl)benzimidazole-5-carboxylic acid Chemical compound C=1C2=CC(C)=CN=C2N=CC=1C1=NC2=CC(C(O)=O)=CC=C2N1C1CCCCC1 DKEFQEQWTNDNNV-UHFFFAOYSA-N 0.000 claims 1
- UCPAWBWTMAABES-UHFFFAOYSA-N 1-cyclohexyl-2-(6-phenyl-1,8-naphthyridin-3-yl)benzimidazole-5-carboxylic acid Chemical compound C=1N=C2N=CC(C=3C=CC=CC=3)=CC2=CC=1C1=NC2=CC(C(=O)O)=CC=C2N1C1CCCCC1 UCPAWBWTMAABES-UHFFFAOYSA-N 0.000 claims 1
- SFWMFKGIWCOMFS-UHFFFAOYSA-N 1-cyclohexyl-2-(7-methyl-1,8-naphthyridin-3-yl)-n-methylsulfonylbenzimidazole-5-carboxamide Chemical compound C1=NC2=NC(C)=CC=C2C=C1C1=NC2=CC(C(=O)NS(C)(=O)=O)=CC=C2N1C1CCCCC1 SFWMFKGIWCOMFS-UHFFFAOYSA-N 0.000 claims 1
- SUBQECRWKXEZEM-UHFFFAOYSA-N 1-cyclohexyl-2-(7-methyl-1,8-naphthyridin-3-yl)benzimidazole-5-carboxylic acid Chemical compound C1=NC2=NC(C)=CC=C2C=C1C1=NC2=CC(C(O)=O)=CC=C2N1C1CCCCC1 SUBQECRWKXEZEM-UHFFFAOYSA-N 0.000 claims 1
- LDPQWIJJGHMNTE-UHFFFAOYSA-N 1-cyclohexyl-2-(7-methylcinnolin-3-yl)benzimidazole-5-carboxylic acid Chemical compound N1=NC2=CC(C)=CC=C2C=C1C1=NC2=CC(C(O)=O)=CC=C2N1C1CCCCC1 LDPQWIJJGHMNTE-UHFFFAOYSA-N 0.000 claims 1
- ZRDWVIXETQVBCJ-UHFFFAOYSA-N 1-cyclohexyl-2-(7-phenyl-1,8-naphthyridin-3-yl)benzimidazole-5-carboxylic acid Chemical compound C=1N=C2N=C(C=3C=CC=CC=3)C=CC2=CC=1C1=NC2=CC(C(=O)O)=CC=C2N1C1CCCCC1 ZRDWVIXETQVBCJ-UHFFFAOYSA-N 0.000 claims 1
- LXUIQUOMODHWDA-UHFFFAOYSA-N 1-cyclohexyl-2-(7-phenylcinnolin-3-yl)benzimidazole-5-carboxylic acid Chemical compound C=1C2=CC=C(C=3C=CC=CC=3)C=C2N=NC=1C1=NC2=CC(C(=O)O)=CC=C2N1C1CCCCC1 LXUIQUOMODHWDA-UHFFFAOYSA-N 0.000 claims 1
- VJNRFZCPZJIOQA-UHFFFAOYSA-N 1-cyclohexyl-2-[2-(3,4-dichlorophenyl)quinolin-6-yl]benzimidazole-5-carboxylic acid Chemical compound C=1C=C2N=C(C=3C=C(Cl)C(Cl)=CC=3)C=CC2=CC=1C1=NC2=CC(C(=O)O)=CC=C2N1C1CCCCC1 VJNRFZCPZJIOQA-UHFFFAOYSA-N 0.000 claims 1
- AZHJJBXSNLQZGO-UHFFFAOYSA-N 1-cyclohexyl-2-[2-(3-hydroxypropyl)quinolin-6-yl]benzimidazole-5-carboxylic acid Chemical compound C1=CC2=NC(CCCO)=CC=C2C=C1C1=NC2=CC(C(O)=O)=CC=C2N1C1CCCCC1 AZHJJBXSNLQZGO-UHFFFAOYSA-N 0.000 claims 1
- VULQLJVXHIDRHI-UHFFFAOYSA-N 1-cyclohexyl-2-[2-(4-morpholin-4-ylphenyl)quinolin-6-yl]benzimidazole-5-carboxylic acid Chemical compound C=1C=C2N=C(C=3C=CC(=CC=3)N3CCOCC3)C=CC2=CC=1C1=NC2=CC(C(=O)O)=CC=C2N1C1CCCCC1 VULQLJVXHIDRHI-UHFFFAOYSA-N 0.000 claims 1
- JIDVYZHWJXTAAM-UHFFFAOYSA-N 1-cyclohexyl-2-[2-(4-phenylphenyl)quinolin-6-yl]benzimidazole-5-carboxylic acid Chemical compound C=1C=C2N=C(C=3C=CC(=CC=3)C=3C=CC=CC=3)C=CC2=CC=1C1=NC2=CC(C(=O)O)=CC=C2N1C1CCCCC1 JIDVYZHWJXTAAM-UHFFFAOYSA-N 0.000 claims 1
- IOJZGAAHYQGJBH-UHFFFAOYSA-N 1-cyclohexyl-2-[2-(5-methyl-2-phenylthiophen-3-yl)quinolin-6-yl]benzimidazole-5-carboxylic acid Chemical compound S1C(C)=CC(C=2N=C3C=CC(=CC3=CC=2)C=2N(C3=CC=C(C=C3N=2)C(O)=O)C2CCCCC2)=C1C1=CC=CC=C1 IOJZGAAHYQGJBH-UHFFFAOYSA-N 0.000 claims 1
- VQUKSGYQFFXFBW-UHFFFAOYSA-N 1-cyclohexyl-2-[2-[2-(2-fluorophenyl)-5-methoxyphenyl]quinolin-6-yl]benzimidazole-5-carboxylic acid Chemical compound C=1C=C2C=C(C=3N(C4=CC=C(C=C4N=3)C(O)=O)C3CCCCC3)C=CC2=NC=1C1=CC(OC)=CC=C1C1=CC=CC=C1F VQUKSGYQFFXFBW-UHFFFAOYSA-N 0.000 claims 1
- RUHSIIWGFOTUQV-UHFFFAOYSA-N 1-cyclohexyl-2-[2-[2-(3,4-difluorophenyl)-5-methoxyphenyl]quinolin-6-yl]benzimidazole-5-carboxylic acid Chemical compound C=1C=C2C=C(C=3N(C4=CC=C(C=C4N=3)C(O)=O)C3CCCCC3)C=CC2=NC=1C1=CC(OC)=CC=C1C1=CC=C(F)C(F)=C1 RUHSIIWGFOTUQV-UHFFFAOYSA-N 0.000 claims 1
- DQAFEIRASMXMJE-UHFFFAOYSA-N 1-cyclohexyl-2-[2-[2-(4-ethylphenyl)-5-methoxyphenyl]quinolin-6-yl]benzimidazole-5-carboxylic acid Chemical compound C1=CC(CC)=CC=C1C1=CC=C(OC)C=C1C1=CC=C(C=C(C=C2)C=3N(C4=CC=C(C=C4N=3)C(O)=O)C3CCCCC3)C2=N1 DQAFEIRASMXMJE-UHFFFAOYSA-N 0.000 claims 1
- TXJUUJQUIXQGFK-UHFFFAOYSA-N 1-cyclohexyl-2-[2-[3-(3,4-dichlorophenyl)-1,2-oxazol-5-yl]quinolin-6-yl]benzimidazole-5-carboxylic acid Chemical compound C=1C=C2N=C(C=3ON=C(C=3)C=3C=C(Cl)C(Cl)=CC=3)C=CC2=CC=1C1=NC2=CC(C(=O)O)=CC=C2N1C1CCCCC1 TXJUUJQUIXQGFK-UHFFFAOYSA-N 0.000 claims 1
- IXOZZJADLDUXKY-UHFFFAOYSA-N 1-cyclohexyl-2-[2-[3-(pyrrolidine-1-carbonyl)phenyl]quinolin-6-yl]benzimidazole-5-carboxylic acid Chemical compound C=1C=C2N=C(C=3C=C(C=CC=3)C(=O)N3CCCC3)C=CC2=CC=1C1=NC2=CC(C(=O)O)=CC=C2N1C1CCCCC1 IXOZZJADLDUXKY-UHFFFAOYSA-N 0.000 claims 1
- YUOTYCJWMXSSNA-UHFFFAOYSA-N 1-cyclohexyl-2-[2-[5-(methylcarbamoyl)-2-phenylphenyl]quinolin-6-yl]benzimidazole-5-carboxylic acid Chemical compound C=1C=C2C=C(C=3N(C4=CC=C(C=C4N=3)C(O)=O)C3CCCCC3)C=CC2=NC=1C1=CC(C(=O)NC)=CC=C1C1=CC=CC=C1 YUOTYCJWMXSSNA-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
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- 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
- C07D401/02—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
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- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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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
- C07D405/02—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 two hetero rings
- C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
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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
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- 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
- C07D417/02—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 two hetero rings
- C07D417/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- 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
-
- 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
- C07D487/04—Ortho-condensed systems
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| CN1829709A (zh) | 2006-09-06 |
| RU2355687C2 (ru) | 2009-05-20 |
| EP1651631A1 (en) | 2006-05-03 |
| TW200517381A (en) | 2005-06-01 |
| NO20061013L (no) | 2006-04-28 |
| IL172975A0 (en) | 2006-06-11 |
| US20050187390A1 (en) | 2005-08-25 |
| CA2534649A1 (en) | 2005-02-10 |
| JP2007501189A (ja) | 2007-01-25 |
| US7511145B2 (en) | 2009-03-31 |
| WO2005012288A1 (en) | 2005-02-10 |
| RU2006106272A (ru) | 2006-08-27 |
| KR20060054410A (ko) | 2006-05-22 |
| BRPI0413234A (pt) | 2006-10-03 |
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