CA2433467A1 - Substituted quinolinecarboxamides as antiviral agents - Google Patents
Substituted quinolinecarboxamides as antiviral agents Download PDFInfo
- Publication number
- CA2433467A1 CA2433467A1 CA002433467A CA2433467A CA2433467A1 CA 2433467 A1 CA2433467 A1 CA 2433467A1 CA 002433467 A CA002433467 A CA 002433467A CA 2433467 A CA2433467 A CA 2433467A CA 2433467 A1 CA2433467 A1 CA 2433467A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- oxo
- chlorobenzyl
- ylmethyl
- dihydroquinoline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 239000003443 antiviral agent Substances 0.000 title abstract description 10
- ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical class C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 118
- -1 morpholinylmethyl Chemical group 0.000 claims description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- VSWHIJKJQVVFJA-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-hydroxyprop-1-ynyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCO)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 VSWHIJKJQVVFJA-UHFFFAOYSA-N 0.000 claims description 15
- 241001529453 unidentified herpesvirus Species 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- 241000282414 Homo sapiens Species 0.000 claims description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 229910052757 nitrogen Chemical group 0.000 claims description 10
- 241000701022 Cytomegalovirus Species 0.000 claims description 9
- 241000701024 Human betaherpesvirus 5 Species 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 241000701085 Human alphaherpesvirus 3 Species 0.000 claims description 7
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- SBFDYTBWVDUUFQ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-methyl-8-[3-(5-methylimidazol-1-yl)prop-1-ynyl]-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound CC1=CN=CN1CC#CC1=CC(CN2CCOCC2)=CC(C2=O)=C1N(C)C=C2C(=O)NCC1=CC=C(Cl)C=C1 SBFDYTBWVDUUFQ-UHFFFAOYSA-N 0.000 claims description 7
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- MGWPYFURPLZGBR-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(4-hydroxybut-1-ynyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCCO)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 MGWPYFURPLZGBR-UHFFFAOYSA-N 0.000 claims description 6
- LIMCXBXZXQIZJC-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(4-hydroxybut-1-ynyl)-1-methyl-6-(oxan-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound O=C1C2=CC(CC3CCOCC3)=CC(C#CCCO)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 LIMCXBXZXQIZJC-UHFFFAOYSA-N 0.000 claims description 6
- FNALQGUDHPRRGW-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(5-hydroxypent-1-ynyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCCCO)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 FNALQGUDHPRRGW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 241000701044 Human gammaherpesvirus 4 Species 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- NYQSBTHWIBQUKL-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxo-8-(2-pyridin-4-ylethynyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CC=3C=CN=CC=3)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 NYQSBTHWIBQUKL-UHFFFAOYSA-N 0.000 claims description 5
- MKITVSKAOUHTMH-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(4-hydroxypent-1-ynyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound C=1C(C(C(C(=O)NCC=2C=CC(Cl)=CC=2)=CN2C)=O)=C2C(C#CCC(O)C)=CC=1CN1CCOCC1 MKITVSKAOUHTMH-UHFFFAOYSA-N 0.000 claims description 5
- GFIYDHXQIDHBOG-GOSISDBHSA-N n-[(4-chlorophenyl)methyl]-8-[(3r)-3-hydroxybut-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound C=1C(C(C(C(=O)NCC=2C=CC(Cl)=CC=2)=CN2C)=O)=C2C(C#C[C@H](O)C)=CC=1CN1CCOCC1 GFIYDHXQIDHBOG-GOSISDBHSA-N 0.000 claims description 5
- SXQAGZQPQZBYCI-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(3-hydroxypiperidin-1-yl)prop-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCN3CC(O)CCC3)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 SXQAGZQPQZBYCI-UHFFFAOYSA-N 0.000 claims description 5
- SMOWTBSZIOTETF-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(dimethylamino)prop-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound C=1C(C(C(C(=O)NCC=2C=CC(Cl)=CC=2)=CN2C)=O)=C2C(C#CCN(C)C)=CC=1CN1CCOCC1 SMOWTBSZIOTETF-UHFFFAOYSA-N 0.000 claims description 5
- QYGAFRCYZAFZAH-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-[2-(2-hydroxyethyl)piperidin-1-yl]prop-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCN3C(CCCC3)CCO)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 QYGAFRCYZAFZAH-UHFFFAOYSA-N 0.000 claims description 5
- UPTHOHQEWDJKIE-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-[4-(2-hydroxyethyl)piperazin-1-yl]prop-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCN3CCN(CCO)CC3)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 UPTHOHQEWDJKIE-UHFFFAOYSA-N 0.000 claims description 5
- QOZAPTVTTIRFKC-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[5-hydroxy-4-(hydroxymethyl)pent-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCC(CO)CO)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 QOZAPTVTTIRFKC-UHFFFAOYSA-N 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
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 206010019972 Herpes viral infections Diseases 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 241000700584 Simplexvirus Species 0.000 claims description 4
- 230000037396 body weight Effects 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- OPJOHUGGAJPPFT-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxo-8-(2-pyridin-3-ylethynyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CC=3C=NC=CC=3)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 OPJOHUGGAJPPFT-UHFFFAOYSA-N 0.000 claims description 4
- PKTJQQZTTYHRPO-XMMPIXPASA-N n-[(4-chlorophenyl)methyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxo-8-[4-[(4r)-2-oxo-1,3-oxazolidin-4-yl]but-1-ynyl]quinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCC[C@H]3NC(=O)OC3)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 PKTJQQZTTYHRPO-XMMPIXPASA-N 0.000 claims description 4
- VCVYCVVYIFPQEG-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-hydroxyprop-1-ynyl)-1-methyl-6-(oxan-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound O=C1C2=CC(CC3CCOCC3)=CC(C#CCO)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 VCVYCVVYIFPQEG-UHFFFAOYSA-N 0.000 claims description 4
- UDGHVURPBHORHE-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-imidazol-1-ylprop-1-ynyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCN3C=NC=C3)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 UDGHVURPBHORHE-UHFFFAOYSA-N 0.000 claims description 4
- GFIYDHXQIDHBOG-SFHVURJKSA-N n-[(4-chlorophenyl)methyl]-8-[(3s)-3-hydroxybut-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound C=1C(C(C(C(=O)NCC=2C=CC(Cl)=CC=2)=CN2C)=O)=C2C(C#C[C@@H](O)C)=CC=1CN1CCOCC1 GFIYDHXQIDHBOG-SFHVURJKSA-N 0.000 claims description 4
- XZQYPQNRUZEBDT-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(dimethylamino)prop-1-ynyl]-1-methyl-6-(oxan-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound C=1C(C(C(C(=O)NCC=2C=CC(Cl)=CC=2)=CN2C)=O)=C2C(C#CCN(C)C)=CC=1CC1CCOCC1 XZQYPQNRUZEBDT-UHFFFAOYSA-N 0.000 claims description 4
- OVZQONYEPMLPOM-SANMLTNESA-N n-[(4-chlorophenyl)methyl]-8-[3-[(2s)-2-(hydroxymethyl)pyrrolidin-1-yl]prop-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCN3[C@@H](CCC3)CO)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 OVZQONYEPMLPOM-SANMLTNESA-N 0.000 claims description 4
- ZBAWVIILDZKQQK-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-[3-(hydroxymethyl)piperidin-1-yl]prop-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCN3CC(CO)CCC3)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 ZBAWVIILDZKQQK-UHFFFAOYSA-N 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 3
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
- FHWSUYOPVRGYSQ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxo-8-(2-pyridin-2-ylethynyl)quinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CC=3N=CC=CC=3)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 FHWSUYOPVRGYSQ-UHFFFAOYSA-N 0.000 claims description 3
- ZRGCVFFOPWYAGJ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(4,5-dichloroimidazol-1-yl)prop-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCN3C(=C(Cl)N=C3)Cl)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 ZRGCVFFOPWYAGJ-UHFFFAOYSA-N 0.000 claims description 3
- ZOGKFJZEKLAULV-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(4-hydroxypiperidin-1-yl)prop-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCN3CCC(O)CC3)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 ZOGKFJZEKLAULV-UHFFFAOYSA-N 0.000 claims description 3
- WZDNQHUHVQSJHR-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-[2,3-dihydroxypropyl(methyl)amino]prop-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound C=1C(C(C(C(=O)NCC=2C=CC(Cl)=CC=2)=CN2C)=O)=C2C(C#CCN(C)CC(O)CO)=CC=1CN1CCOCC1 WZDNQHUHVQSJHR-UHFFFAOYSA-N 0.000 claims description 3
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 3
- 150000002923 oximes Chemical class 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 3
- SMIJBCNUGPFFIO-UHFFFAOYSA-N 8-[3-[butyl(2-hydroxyethyl)amino]prop-1-ynyl]-n-[(4-chlorophenyl)methyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound C=1C(C(C(C(=O)NCC=2C=CC(Cl)=CC=2)=CN2C)=O)=C2C(C#CCN(CCO)CCCC)=CC=1CN1CCOCC1 SMIJBCNUGPFFIO-UHFFFAOYSA-N 0.000 claims description 2
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 claims description 2
- 108020005202 Viral DNA Proteins 0.000 claims description 2
- AHTWPTOJRMBDCN-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-fluoroprop-1-ynyl)-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCF)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 AHTWPTOJRMBDCN-UHFFFAOYSA-N 0.000 claims description 2
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- IQICEVRDCOHUEE-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(1,1-dioxo-1,4-thiazinan-4-yl)prop-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCN3CCS(=O)(=O)CC3)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 IQICEVRDCOHUEE-UHFFFAOYSA-N 0.000 claims 2
- KVWPVZONWRAHLF-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(3-hydroxypyrrolidin-1-yl)prop-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCN3CC(O)CC3)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 KVWPVZONWRAHLF-UHFFFAOYSA-N 0.000 claims 2
- OVZQONYEPMLPOM-AREMUKBSSA-N n-[(4-chlorophenyl)methyl]-8-[3-[(2r)-2-(hydroxymethyl)pyrrolidin-1-yl]prop-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound O=C1C2=CC(CN3CCOCC3)=CC(C#CCN3[C@H](CCC3)CO)=C2N(C)C=C1C(=O)NCC1=CC=C(Cl)C=C1 OVZQONYEPMLPOM-AREMUKBSSA-N 0.000 claims 2
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- UIYLHDWLEFCUHE-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-[2-hydroxyethyl(methyl)amino]prop-1-ynyl]-1-methyl-6-(morpholin-4-ylmethyl)-4-oxoquinoline-3-carboxamide Chemical compound C=1C(C(C(C(=O)NCC=2C=CC(Cl)=CC=2)=CN2C)=O)=C2C(C#CCN(CCO)C)=CC=1CN1CCOCC1 UIYLHDWLEFCUHE-UHFFFAOYSA-N 0.000 claims 1
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
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- CVAWACBLSANHSQ-UHFFFAOYSA-N 4-oxo-1h-quinoline-3-carboxamide Chemical class C1=CC=CC2=C(O)C(C(=O)N)=CN=C21 CVAWACBLSANHSQ-UHFFFAOYSA-N 0.000 abstract description 2
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 abstract description 2
- 241000700605 Viruses Species 0.000 abstract description 2
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 294
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 105
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- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
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- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 description 1
- NUAFULZXWAVICA-UHFFFAOYSA-N n-(oxan-2-ylmethyl)aniline Chemical compound C1CCCOC1CNC1=CC=CC=C1 NUAFULZXWAVICA-UHFFFAOYSA-N 0.000 description 1
- 239000007922 nasal spray Substances 0.000 description 1
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- 239000006199 nebulizer Substances 0.000 description 1
- 231100000344 non-irritating Toxicity 0.000 description 1
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- 235000019198 oils Nutrition 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
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- 206010033072 otitis externa Diseases 0.000 description 1
- JMJRYTGVHCAYCT-UHFFFAOYSA-N oxan-4-one Chemical compound O=C1CCOCC1 JMJRYTGVHCAYCT-UHFFFAOYSA-N 0.000 description 1
- OOFGXDQWDNJDIS-UHFFFAOYSA-N oxathiolane Chemical compound C1COSC1 OOFGXDQWDNJDIS-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- PMOIAJVKYNVHQE-UHFFFAOYSA-N phosphanium;bromide Chemical compound [PH4+].[Br-] PMOIAJVKYNVHQE-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- BIWOSRSKDCZIFM-UHFFFAOYSA-N piperidin-3-ol Chemical compound OC1CCCNC1 BIWOSRSKDCZIFM-UHFFFAOYSA-N 0.000 description 1
- HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
- 235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
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- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- JHHZLHWJQPUNKB-UHFFFAOYSA-N pyrrolidin-3-ol Chemical compound OC1CCNC1 JHHZLHWJQPUNKB-UHFFFAOYSA-N 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- DJXNJVFEFSWHLY-UHFFFAOYSA-N quinoline-3-carboxylic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CN=C21 DJXNJVFEFSWHLY-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- GHBFNMLVSPCDGN-UHFFFAOYSA-N rac-1-monooctanoylglycerol Chemical compound CCCCCCCC(=O)OCC(O)CO GHBFNMLVSPCDGN-UHFFFAOYSA-N 0.000 description 1
- 230000007420 reactivation Effects 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
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- 239000002002 slurry Substances 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000001587 sorbitan monostearate Substances 0.000 description 1
- 235000011076 sorbitan monostearate Nutrition 0.000 description 1
- 229940035048 sorbitan monostearate Drugs 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- ODEAGBKJOAYUGE-UHFFFAOYSA-N tert-butyl-[2-[[tert-butyl(diphenyl)silyl]oxymethyl]pent-4-ynoxy]-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(C(C)(C)C)OCC(CC#C)CO[Si](C(C)(C)C)(C=1C=CC=CC=1)C1=CC=CC=C1 ODEAGBKJOAYUGE-UHFFFAOYSA-N 0.000 description 1
- MHXBHWLGRWOABW-UHFFFAOYSA-N tetradecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC MHXBHWLGRWOABW-UHFFFAOYSA-N 0.000 description 1
- 125000006173 tetrahydropyranylmethyl group Chemical group 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- SDCRCIBCGZZNPR-UHFFFAOYSA-N trimethylazanium;carbonate Chemical compound C[NH+](C)C.C[NH+](C)C.[O-]C([O-])=O SDCRCIBCGZZNPR-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 102000003390 tumor necrosis factor Human genes 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C07D401/06—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 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
- C07D413/02—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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Virology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27260701P | 2001-03-01 | 2001-03-01 | |
| US60/272,607 | 2001-03-01 | ||
| PCT/US2002/003407 WO2002070487A1 (en) | 2001-03-01 | 2002-02-27 | Substituted quinolinecarboxamides as antiviral agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2433467A1 true CA2433467A1 (en) | 2002-09-12 |
Family
ID=23040509
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002433467A Abandoned CA2433467A1 (en) | 2001-03-01 | 2002-02-27 | Substituted quinolinecarboxamides as antiviral agents |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US6544990B2 (enExample) |
| EP (1) | EP1363887A1 (enExample) |
| JP (1) | JP2004520424A (enExample) |
| CA (1) | CA2433467A1 (enExample) |
| PE (1) | PE20020974A1 (enExample) |
| WO (1) | WO2002070487A1 (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2433467A1 (en) * | 2001-03-01 | 2002-09-12 | Joseph W. Strohbach | Substituted quinolinecarboxamides as antiviral agents |
| WO2004019933A1 (en) * | 2002-08-30 | 2004-03-11 | Pharmacia & Upjohn Company | Method of preventing or treating atherosclerosis or restenosis |
| US20040186131A1 (en) * | 2002-08-30 | 2004-09-23 | Wathen Michael W | Method of preventing or treating atherosclerosis or restenosis |
| MXPA06000675A (es) | 2003-07-24 | 2006-04-19 | Astellas Pharma Inc | Derivado de quinolona o sal del mismo. |
| CN100532362C (zh) * | 2004-04-13 | 2009-08-26 | 中国科学院化学研究所 | 酯类反应性溶剂制备碘化n-甲基喹啉类化合物的方法 |
| SG11201502935VA (en) | 2012-10-16 | 2015-09-29 | Janssen Pharmaceutica Nv | Phenyl linked quinolinyl modulators of ror-gamma-t |
| AU2013331496B2 (en) | 2012-10-16 | 2017-07-27 | Janssen Pharmaceutica Nv | Methylene linked quinolinyl modulators of ROR-gamma-t |
| WO2014062655A1 (en) | 2012-10-16 | 2014-04-24 | Janssen Pharmaceutica Nv | HETEROARYL LINKED QUINOLINYL MODULATORS OF RORyt |
| WO2014070976A1 (en) * | 2012-11-03 | 2014-05-08 | Boehringer Ingelheim International Gmbh | Inhibitors of cytomegalovirus |
| US9328095B2 (en) | 2013-10-15 | 2016-05-03 | Janssen Pharmaceutica Nv | Heteroaryl linked quinolinyl modulators of RORgammat |
| AU2014334616A1 (en) | 2013-10-15 | 2016-04-28 | Janssen Pharmaceutica Nv | Quinolinyl modulators of RORyt |
| US9221804B2 (en) | 2013-10-15 | 2015-12-29 | Janssen Pharmaceutica Nv | Secondary alcohol quinolinyl modulators of RORγt |
| US9403816B2 (en) | 2013-10-15 | 2016-08-02 | Janssen Pharmaceutica Nv | Phenyl linked quinolinyl modulators of RORγt |
| US9284308B2 (en) | 2013-10-15 | 2016-03-15 | Janssen Pharmaceutica Nv | Methylene linked quinolinyl modulators of RORγt |
| US9346782B2 (en) | 2013-10-15 | 2016-05-24 | Janssen Pharmaceutica Nv | Alkyl linked quinolinyl modulators of RORγt |
| US10555941B2 (en) | 2013-10-15 | 2020-02-11 | Janssen Pharmaceutica Nv | Alkyl linked quinolinyl modulators of RORγt |
| EP3849979A1 (en) | 2018-09-12 | 2021-07-21 | Novartis AG | Antiviral pyridopyrazinedione compounds |
| KR20250127350A (ko) | 2019-09-26 | 2025-08-26 | 노파르티스 아게 | 항바이러스성 피라졸로피리디논 화합물 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE239477T1 (de) | 1995-08-02 | 2003-05-15 | Darwin Discovery Ltd | Chinolone und deren therapeutische verwendung |
| DE69831506T2 (de) | 1997-12-22 | 2006-06-29 | Pharmacia & Upjohn Co. Llc, Kalamazoo | 4-hydroxychinolin-3-carboxamide und hydrazide als antivirale wirkstoffe |
| US6248736B1 (en) * | 1999-01-08 | 2001-06-19 | Pharmacia & Upjohn Company | 4-oxo-1,4-dihydro-3-quinolinecarboxamides as antiviral agents |
| US6248739B1 (en) * | 1999-01-08 | 2001-06-19 | Pharmacia & Upjohn Company | Quinolinecarboxamides as antiviral agents |
| US6682892B2 (en) * | 2000-07-13 | 2004-01-27 | Pharmacia & Upjohn Company | Method for treating herpes viruses |
| CA2433467A1 (en) * | 2001-03-01 | 2002-09-12 | Joseph W. Strohbach | Substituted quinolinecarboxamides as antiviral agents |
-
2002
- 2002-02-27 CA CA002433467A patent/CA2433467A1/en not_active Abandoned
- 2002-02-27 US US10/084,015 patent/US6544990B2/en not_active Expired - Fee Related
- 2002-02-27 WO PCT/US2002/003407 patent/WO2002070487A1/en not_active Ceased
- 2002-02-27 EP EP02709361A patent/EP1363887A1/en not_active Withdrawn
- 2002-02-27 JP JP2002569807A patent/JP2004520424A/ja not_active Withdrawn
- 2002-02-28 PE PE2002000167A patent/PE20020974A1/es not_active Application Discontinuation
-
2003
- 2003-01-23 US US10/350,248 patent/US6727248B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20020165253A1 (en) | 2002-11-07 |
| US20030149035A1 (en) | 2003-08-07 |
| US6544990B2 (en) | 2003-04-08 |
| US6727248B2 (en) | 2004-04-27 |
| EP1363887A1 (en) | 2003-11-26 |
| WO2002070487A1 (en) | 2002-09-12 |
| JP2004520424A (ja) | 2004-07-08 |
| PE20020974A1 (es) | 2002-10-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |