ZA200207540B - 4-oxo-1,4-dihydro-3-cinnolinecarboxamides and antiviral agents. - Google Patents
4-oxo-1,4-dihydro-3-cinnolinecarboxamides and antiviral agents. Download PDFInfo
- Publication number
- ZA200207540B ZA200207540B ZA200207540A ZA200207540A ZA200207540B ZA 200207540 B ZA200207540 B ZA 200207540B ZA 200207540 A ZA200207540 A ZA 200207540A ZA 200207540 A ZA200207540 A ZA 200207540A ZA 200207540 B ZA200207540 B ZA 200207540B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- dihydro
- chlorobenzyl
- cinnolinecarboxamide
- oxo
- Prior art date
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- 239000003443 antiviral agent Substances 0.000 title description 4
- IJAVOENDLHVSER-UHFFFAOYSA-N 4-oxo-1h-cinnoline-3-carboxamide Chemical class C1=CC=CC2=C(O)C(C(=O)N)=NN=C21 IJAVOENDLHVSER-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 41
- -1 bicyclic carbocyclic radical Chemical class 0.000 claims description 38
- 125000003118 aryl group Chemical group 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 31
- 239000000203 mixture Substances 0.000 claims description 30
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 241000124008 Mammalia Species 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 208000036142 Viral infection Diseases 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 230000009385 viral infection Effects 0.000 claims description 7
- 241000701085 Human alphaherpesvirus 3 Species 0.000 claims description 6
- 241000701024 Human betaherpesvirus 5 Species 0.000 claims description 6
- 241000701044 Human gammaherpesvirus 4 Species 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 claims description 5
- 241000282414 Homo sapiens Species 0.000 claims description 5
- 241000700588 Human alphaherpesvirus 1 Species 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000005842 heteroatom Chemical group 0.000 claims description 5
- 238000001727 in vivo Methods 0.000 claims description 5
- 208000015181 infectious disease Diseases 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 206010019972 Herpes viral infections Diseases 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims description 4
- 238000000338 in vitro Methods 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 229910052744 lithium Chemical group 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 150000002923 oximes Chemical class 0.000 claims description 3
- 239000011591 potassium Chemical group 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 239000011734 sodium Substances 0.000 claims description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 3
- 208000029433 Herpesviridae infectious disease Diseases 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 21
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 8
- 230000037396 body weight Effects 0.000 claims 6
- 150000001408 amides Chemical class 0.000 claims 4
- 241001465754 Metazoa Species 0.000 claims 3
- 108020005202 Viral DNA Proteins 0.000 claims 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 3
- 244000144972 livestock Species 0.000 claims 3
- KFVKJOGHROHASP-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(hydroxymethyl)-1-methyl-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CO)=CC=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 KFVKJOGHROHASP-UHFFFAOYSA-N 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- VREVBHMMPSREDI-UHFFFAOYSA-N 1,4-dihydrocinnoline-3-carboxamide Chemical compound C1=CC=C2CC(C(=O)N)=NNC2=C1 VREVBHMMPSREDI-UHFFFAOYSA-N 0.000 claims 2
- NVKURPSLPZAWIE-UHFFFAOYSA-N 1-(benzenesulfinylmethyl)-n-[(4-chlorophenyl)methyl]-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1CNC(=O)C(C(C1=CC(CN2CCOCC2)=CC=C11)=O)=NN1CS(=O)C1=CC=CC=C1 NVKURPSLPZAWIE-UHFFFAOYSA-N 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- JQELSVSXEAZYQG-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-(1,2-diethylpyrazolidin-4-yl)-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound C1N(CC)N(CC)CC1N1C2=CC=C(CN3CCOCC3)C=C2C(=O)C(C(=O)NCC=2C=CC(Cl)=CC=2)=N1 JQELSVSXEAZYQG-UHFFFAOYSA-N 0.000 claims 2
- UVOIGLFJNPNGTJ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-methyl-6,8-bis(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(CN3CCOCC3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 UVOIGLFJNPNGTJ-UHFFFAOYSA-N 0.000 claims 2
- LAMQEKZKURLPJA-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 LAMQEKZKURLPJA-UHFFFAOYSA-N 0.000 claims 2
- XIPHMDKBQRFMMS-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-methyl-6-(oxan-4-ylmethyl)-4-oxo-8-(2-phenylethyl)cinnoline-3-carboxamide Chemical compound O=C1C2=CC(CC3CCOCC3)=CC(CCC=3C=CC=CC=3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 XIPHMDKBQRFMMS-UHFFFAOYSA-N 0.000 claims 2
- WACKJXWKGISGMV-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(3-hydroxyprop-1-ynyl)-1-methyl-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(C#CCO)=CC=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 WACKJXWKGISGMV-UHFFFAOYSA-N 0.000 claims 2
- IGGBOIMQUDGDFQ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(4-hydroxybut-1-ynyl)-1-methyl-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(C#CCCO)=CC=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 IGGBOIMQUDGDFQ-UHFFFAOYSA-N 0.000 claims 2
- RRFKOBJOHHGLCM-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(morpholin-4-ylmethyl)-1-(oxan-3-yl)-4-oxocinnoline-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1CNC(=O)C(C(C1=CC(CN2CCOCC2)=CC=C11)=O)=NN1C1COCCC1 RRFKOBJOHHGLCM-UHFFFAOYSA-N 0.000 claims 2
- SNUYVQJIKTXKGA-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(morpholin-4-ylmethyl)-1-(oxan-4-yl)-4-oxocinnoline-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1CNC(=O)C(C(C1=CC(CN2CCOCC2)=CC=C11)=O)=NN1C1CCOCC1 SNUYVQJIKTXKGA-UHFFFAOYSA-N 0.000 claims 2
- DIJXTTVQLNYFCS-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(morpholin-4-ylmethyl)-1-(oxetan-3-yl)-4-oxocinnoline-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1CNC(=O)C(C(C1=CC(CN2CCOCC2)=CC=C11)=O)=NN1C1COC1 DIJXTTVQLNYFCS-UHFFFAOYSA-N 0.000 claims 2
- DXNMWWQCKMIYFV-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(morpholin-4-ylmethyl)-4-oxo-1-(oxolan-3-yl)cinnoline-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1CNC(=O)C(C(C1=CC(CN2CCOCC2)=CC=C11)=O)=NN1C1COCC1 DXNMWWQCKMIYFV-UHFFFAOYSA-N 0.000 claims 2
- UTMWGKILIFRFBR-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-iodo-1-methyl-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(I)=CC=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 UTMWGKILIFRFBR-UHFFFAOYSA-N 0.000 claims 2
- ATXHYNPFBGCDQN-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(2-cyclopropylethyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(CCC3CC3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 ATXHYNPFBGCDQN-UHFFFAOYSA-N 0.000 claims 2
- UEWGZGQKIXOLPF-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3,3-dicyclopropyl-3-hydroxypropyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(CCC(O)(C3CC3)C3CC3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 UEWGZGQKIXOLPF-UHFFFAOYSA-N 0.000 claims 2
- GBHCGGPRZKPKES-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-hydroxy-3-methylbut-1-ynyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CC(C)(C)O)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 GBHCGGPRZKPKES-UHFFFAOYSA-N 0.000 claims 2
- DJYOHWGIPSKPAT-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-hydroxyprop-1-ynyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCO)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 DJYOHWGIPSKPAT-UHFFFAOYSA-N 0.000 claims 2
- SBLCHJYDKKKTOC-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-hydroxypropyl)-1-methyl-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC=CC(CCCO)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 SBLCHJYDKKKTOC-UHFFFAOYSA-N 0.000 claims 2
- SPLMJVOOWMLCFK-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(4-hydroxybut-1-ynyl)-1-methyl-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC=CC(C#CCCO)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 SPLMJVOOWMLCFK-UHFFFAOYSA-N 0.000 claims 2
- FYJCXIBSPQCCSQ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(5-hydroxypent-1-ynyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCCCO)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 FYJCXIBSPQCCSQ-UHFFFAOYSA-N 0.000 claims 2
- SJZXJLIBQCRCQS-QGZVFWFLSA-N n-[(4-chlorophenyl)methyl]-8-[(3r)-3-hydroxybut-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound C=1C(C(C(C(=O)NCC=2C=CC(Cl)=CC=2)=NN2C)=O)=C2C(C#C[C@H](O)C)=CC=1CN1CCOCC1 SJZXJLIBQCRCQS-QGZVFWFLSA-N 0.000 claims 2
- AIAZXAVEVBLIAQ-KRWDZBQOSA-N n-[(4-chlorophenyl)methyl]-8-[(3s)-3-hydroxybutyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound C=1C(C(C(C(=O)NCC=2C=CC(Cl)=CC=2)=NN2C)=O)=C2C(CC[C@@H](O)C)=CC=1CN1CCOCC1 AIAZXAVEVBLIAQ-KRWDZBQOSA-N 0.000 claims 2
- RVFBGAQJNVCMBS-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[2-(1-hydroxycyclohexyl)ethyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(CCC3(O)CCCCC3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 RVFBGAQJNVCMBS-UHFFFAOYSA-N 0.000 claims 2
- DCMFWMPJGDVNEW-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[2-(1-hydroxycyclohexyl)ethynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CC3(O)CCCCC3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 DCMFWMPJGDVNEW-UHFFFAOYSA-N 0.000 claims 2
- HXBNMPRHFDJPCD-BWKNWUBXSA-N n-[(4-chlorophenyl)methyl]-8-[2-[(1r,2s)-2-hydroxycyclopentyl]ethynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#C[C@@H]3[C@H](CCC3)O)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 HXBNMPRHFDJPCD-BWKNWUBXSA-N 0.000 claims 2
- NVAXPHSKHMJWOM-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(1,1-dioxo-1,4-thiazinan-4-yl)propyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(CCCN3CCS(=O)(=O)CC3)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 NVAXPHSKHMJWOM-UHFFFAOYSA-N 0.000 claims 2
- ZBOAFXQQXAADNF-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(4,5-dichloroimidazol-1-yl)propyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(CCCN3C(=C(Cl)N=C3)Cl)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 ZBOAFXQQXAADNF-UHFFFAOYSA-N 0.000 claims 2
- OWCVBVOMDOQVNL-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(dimethylamino)propyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound C=1C(C(C(C(=O)NCC=2C=CC(Cl)=CC=2)=NN2C)=O)=C2C(CCCN(C)C)=CC=1CN1CCOCC1 OWCVBVOMDOQVNL-UHFFFAOYSA-N 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- MMDKFHVBVDGYLB-UHFFFAOYSA-N 1-(benzenesulfonylmethyl)-n-[(4-chlorophenyl)methyl]-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound C1=CC(Cl)=CC=C1CNC(=O)C(C(C1=CC(CN2CCOCC2)=CC=C11)=O)=NN1CS(=O)(=O)C1=CC=CC=C1 MMDKFHVBVDGYLB-UHFFFAOYSA-N 0.000 claims 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 claims 1
- XTTZBGVSJSCQQZ-UHFFFAOYSA-N 8-[(1-acetylpiperidin-4-yl)amino]-n-[(4-chlorophenyl)methyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound C1CN(C(=O)C)CCC1NC1=CC(CN2CCOCC2)=CC(C2=O)=C1N(C)N=C2C(=O)NCC1=CC=C(Cl)C=C1 XTTZBGVSJSCQQZ-UHFFFAOYSA-N 0.000 claims 1
- FAXGYPWIXVQXPT-UHFFFAOYSA-N 8-[3-(carbamoylamino)-3-methylbut-1-ynyl]-n-[(4-chlorophenyl)methyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CC(C)(C)NC(N)=O)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 FAXGYPWIXVQXPT-UHFFFAOYSA-N 0.000 claims 1
- IHDSDLMCWZEFIM-UHFFFAOYSA-N 8-amino-n-[(4-chlorophenyl)methyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(N)=C2N(C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 IHDSDLMCWZEFIM-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 claims 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 1
- STUHQDIOZQUPGP-UHFFFAOYSA-N morpholin-4-ium-4-carboxylate Chemical compound OC(=O)N1CCOCC1 STUHQDIOZQUPGP-UHFFFAOYSA-N 0.000 claims 1
- CJKBAAGRIMRQHY-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-(2-hydroxyethoxymethyl)-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC=C2N(COCCO)N=C1C(=O)NCC1=CC=C(Cl)C=C1 CJKBAAGRIMRQHY-UHFFFAOYSA-N 0.000 claims 1
- HWVBLJDVOIKCCO-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-(3-methylsulfanylpropyl)-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC=C2N(CCCSC)N=C1C(=O)NCC1=CC=C(Cl)C=C1 HWVBLJDVOIKCCO-UHFFFAOYSA-N 0.000 claims 1
- PESYDWOLBHBIGV-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-(3-methylsulfonylpropyl)-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC=C2N(CCCS(=O)(=O)C)N=C1C(=O)NCC1=CC=C(Cl)C=C1 PESYDWOLBHBIGV-UHFFFAOYSA-N 0.000 claims 1
- NGFJCAKCMZRCEV-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-(methylsulfanylmethyl)-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC=C2N(CSC)N=C1C(=O)NCC1=CC=C(Cl)C=C1 NGFJCAKCMZRCEV-UHFFFAOYSA-N 0.000 claims 1
- QHWRMCLRCGPHNA-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-[2-(2-ethoxyethoxy)ethyl]-6-(morpholin-4-ylmethyl)-4-oxocinnoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC=C2N(CCOCCOCC)N=C1C(=O)NCC1=CC=C(Cl)C=C1 QHWRMCLRCGPHNA-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/28—Cinnolines
-
- 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
- C07D403/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D405/06—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 linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19129100P | 2000-03-21 | 2000-03-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200207540B true ZA200207540B (en) | 2003-12-19 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200207540A ZA200207540B (en) | 2000-03-21 | 2002-09-19 | 4-oxo-1,4-dihydro-3-cinnolinecarboxamides and antiviral agents. |
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| EP (1) | EP1265873B1 (ko) |
| JP (1) | JP2003528087A (ko) |
| KR (1) | KR20020081479A (ko) |
| CN (1) | CN1406228A (ko) |
| AR (1) | AR027978A1 (ko) |
| AT (1) | ATE252086T1 (ko) |
| AU (1) | AU2001247224A1 (ko) |
| BR (1) | BR0109487A (ko) |
| CA (1) | CA2400000A1 (ko) |
| CZ (1) | CZ20023141A3 (ko) |
| DE (1) | DE60100999T2 (ko) |
| DK (1) | DK1265873T3 (ko) |
| EA (1) | EA200201002A1 (ko) |
| EE (1) | EE200200541A (ko) |
| ES (1) | ES2208581T3 (ko) |
| HK (1) | HK1052694A1 (ko) |
| HU (1) | HUP0300326A3 (ko) |
| IL (1) | IL151787A0 (ko) |
| MX (1) | MXPA02009251A (ko) |
| NO (1) | NO20024502L (ko) |
| NZ (1) | NZ521524A (ko) |
| PL (1) | PL357443A1 (ko) |
| PT (1) | PT1265873E (ko) |
| SI (1) | SI1265873T1 (ko) |
| SK (1) | SK12102002A3 (ko) |
| WO (1) | WO2001070706A2 (ko) |
| ZA (1) | ZA200207540B (ko) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20011349A1 (es) * | 2000-06-16 | 2002-01-19 | Upjohn Co | 1-aril-4-oxo-1,4-dihidro-3-quinolincarboxamidas como agentes antivirales |
| JP6237779B2 (ja) * | 2012-11-03 | 2017-11-29 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | サイトメガロウイルスの阻害薬 |
| WO2020053654A1 (en) | 2018-09-12 | 2020-03-19 | Novartis Ag | Antiviral pyridopyrazinedione compounds |
| AU2020353055B2 (en) | 2019-09-26 | 2024-03-07 | Gilead Sciences, Inc. | Antiviral pyrazolopyridinone compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8513639D0 (en) | 1985-05-30 | 1985-07-03 | Ici America Inc | Cinnoline compounds |
| GB8702288D0 (en) | 1987-02-02 | 1987-03-11 | Erba Farmitalia | Cinnoline-carboxamides |
| PT841929E (pt) | 1995-08-02 | 2003-09-30 | Darwin Discovery Ltd | Quinolonas e sua utilizacao terapeutica |
| AU695132B2 (en) | 1995-08-02 | 1998-08-06 | Darwin Discovery Limited | Quinolones and their therapeutic use |
| ES2248923T3 (es) | 1997-12-22 | 2006-03-16 | PHARMACIA & UPJOHN COMPANY LLC | 4-hydroxiquinolin-3-carboxamidas y hidrazidas como agentes antivirales. |
| AU763636C (en) | 1998-01-29 | 2004-05-27 | Daiichi Asubio Pharma Co., Ltd. | 1-cycloalkyl-1,8-naphthyridin-4-one derivatives with phosphodiesterase IV inhibitory activity |
-
2001
- 2001-03-15 JP JP2001568916A patent/JP2003528087A/ja active Pending
- 2001-03-15 SI SI200130046T patent/SI1265873T1/xx unknown
- 2001-03-15 MX MXPA02009251A patent/MXPA02009251A/es active IP Right Grant
- 2001-03-15 WO PCT/US2001/005811 patent/WO2001070706A2/en active IP Right Grant
- 2001-03-15 EE EEP200200541A patent/EE200200541A/xx unknown
- 2001-03-15 CZ CZ20023141A patent/CZ20023141A3/cs unknown
- 2001-03-15 HU HU0300326A patent/HUP0300326A3/hu unknown
- 2001-03-15 CA CA002400000A patent/CA2400000A1/en not_active Abandoned
- 2001-03-15 NZ NZ521524A patent/NZ521524A/en unknown
- 2001-03-15 SK SK1210-2002A patent/SK12102002A3/sk unknown
- 2001-03-15 EP EP01920138A patent/EP1265873B1/en not_active Expired - Lifetime
- 2001-03-15 KR KR1020027012466A patent/KR20020081479A/ko not_active Application Discontinuation
- 2001-03-15 EA EA200201002A patent/EA200201002A1/ru unknown
- 2001-03-15 AT AT01920138T patent/ATE252086T1/de not_active IP Right Cessation
- 2001-03-15 ES ES01920138T patent/ES2208581T3/es not_active Expired - Lifetime
- 2001-03-15 IL IL15178701A patent/IL151787A0/xx unknown
- 2001-03-15 AU AU2001247224A patent/AU2001247224A1/en not_active Abandoned
- 2001-03-15 CN CN01805756A patent/CN1406228A/zh active Pending
- 2001-03-15 BR BR0109487-4A patent/BR0109487A/pt not_active IP Right Cessation
- 2001-03-15 DE DE60100999T patent/DE60100999T2/de not_active Expired - Fee Related
- 2001-03-15 US US09/808,836 patent/US6624160B2/en not_active Expired - Fee Related
- 2001-03-15 PL PL01357443A patent/PL357443A1/xx not_active Application Discontinuation
- 2001-03-15 DK DK01920138T patent/DK1265873T3/da active
- 2001-03-15 PT PT01920138T patent/PT1265873E/pt unknown
- 2001-03-20 AR ARP010101303A patent/AR027978A1/es unknown
-
2002
- 2002-09-19 ZA ZA200207540A patent/ZA200207540B/en unknown
- 2002-09-20 NO NO20024502A patent/NO20024502L/no not_active Application Discontinuation
-
2003
- 2003-07-09 HK HK03104900.8A patent/HK1052694A1/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2001247224A1 (en) | 2001-10-03 |
| PT1265873E (pt) | 2004-03-31 |
| ATE252086T1 (de) | 2003-11-15 |
| NZ521524A (en) | 2004-04-30 |
| MXPA02009251A (es) | 2004-04-05 |
| SI1265873T1 (en) | 2004-02-29 |
| CZ20023141A3 (cs) | 2003-02-12 |
| DK1265873T3 (da) | 2004-02-16 |
| BR0109487A (pt) | 2003-06-10 |
| EE200200541A (et) | 2004-04-15 |
| IL151787A0 (en) | 2003-04-10 |
| HK1052694A1 (zh) | 2003-09-26 |
| HUP0300326A3 (en) | 2003-09-29 |
| NO20024502L (no) | 2002-11-20 |
| KR20020081479A (ko) | 2002-10-26 |
| CA2400000A1 (en) | 2001-09-27 |
| WO2001070706A2 (en) | 2001-09-27 |
| EA200201002A1 (ru) | 2003-02-27 |
| DE60100999D1 (en) | 2003-11-20 |
| SK12102002A3 (sk) | 2003-03-04 |
| AR027978A1 (es) | 2003-04-23 |
| HUP0300326A2 (hu) | 2003-07-28 |
| US6624160B2 (en) | 2003-09-23 |
| DE60100999T2 (de) | 2004-09-02 |
| WO2001070706A3 (en) | 2002-05-10 |
| PL357443A1 (en) | 2004-07-26 |
| EP1265873A2 (en) | 2002-12-18 |
| ES2208581T3 (es) | 2004-06-16 |
| JP2003528087A (ja) | 2003-09-24 |
| EP1265873B1 (en) | 2003-10-15 |
| CN1406228A (zh) | 2003-03-26 |
| US20020045619A1 (en) | 2002-04-18 |
| NO20024502D0 (no) | 2002-09-20 |
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