ZA200207543B - 4-hydroxycinnoline-3-carboxyamides as antiviral agents. - Google Patents
4-hydroxycinnoline-3-carboxyamides as antiviral agents. Download PDFInfo
- Publication number
- ZA200207543B ZA200207543B ZA200207543A ZA200207543A ZA200207543B ZA 200207543 B ZA200207543 B ZA 200207543B ZA 200207543 A ZA200207543 A ZA 200207543A ZA 200207543 A ZA200207543 A ZA 200207543A ZA 200207543 B ZA200207543 B ZA 200207543B
- Authority
- ZA
- South Africa
- Prior art keywords
- hydroxy
- chlorobenzyl
- cinnolinecarboxamide
- morpholinylmethyl
- pyran
- Prior art date
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- 239000003443 antiviral agent Substances 0.000 title description 5
- GYKBFNVIWCCYQA-UHFFFAOYSA-N 2-(4-oxo-1H-cinnolin-3-yl)acetamide Chemical class OC1=C(N=NC2=CC=CC=C12)CC(=O)N GYKBFNVIWCCYQA-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- -1 cyano, phenyl Chemical group 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 241000124008 Mammalia Species 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 9
- 208000036142 Viral infection Diseases 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
- 241000701044 Human gammaherpesvirus 4 Species 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 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
- 241000701024 Human betaherpesvirus 5 Species 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000002618 bicyclic heterocycle group Chemical group 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 125000002837 carbocyclic group Chemical group 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 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
- 208000029433 Herpesviridae infectious disease Diseases 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 21
- 230000037396 body weight Effects 0.000 claims 6
- 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
- KFZFJTZYXHXVQH-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(hydroxymethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound O=C1C2=CC(CO)=CC=C2NN=C1C(=O)NCC1=CC=C(Cl)C=C1 KFZFJTZYXHXVQH-UHFFFAOYSA-N 0.000 claims 3
- ZAXAMTDTQDBBMQ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C1=C2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)N=NC2=CC=C1CN1CCOCC1 ZAXAMTDTQDBBMQ-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 2
- WKSKKVDMZYMYHS-UHFFFAOYSA-N methyl 3-[(4-chlorophenyl)methylcarbamoyl]-4-oxo-1h-cinnoline-6-carboxylate Chemical compound O=C1C2=CC(C(=O)OC)=CC=C2NN=C1C(=O)NCC1=CC=C(Cl)C=C1 WKSKKVDMZYMYHS-UHFFFAOYSA-N 0.000 claims 2
- NTHRKKXGDSVVBM-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(oxan-4-ylmethyl)-4-oxo-8-(2-phenylethyl)-1h-cinnoline-3-carboxamide Chemical compound C1=C(CC2CCOCC2)C=C2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)N=NC2=C1CCC1=CC=CC=C1 NTHRKKXGDSVVBM-UHFFFAOYSA-N 0.000 claims 2
- QNFJUNYZKAMLTP-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(oxan-4-ylmethyl)-4-oxo-8-(2-phenylethynyl)-1h-cinnoline-3-carboxamide Chemical compound C1=C2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)N=NC2=C(C#CC=2C=CC=CC=2)C=C1CC1CCOCC1 QNFJUNYZKAMLTP-UHFFFAOYSA-N 0.000 claims 2
- UPOZVSMQNMFSBD-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3,3-dicyclopropyl-3-hydroxyprop-1-ynyl)-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C1=C2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)N=NC2=C(C#CC(O)(C2CC2)C2CC2)C=C1CN1CCOCC1 UPOZVSMQNMFSBD-UHFFFAOYSA-N 0.000 claims 2
- ARBGSRDZYJRBBH-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-hydroxy-3-methylbut-1-ynyl)-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(C#CC(C)(O)C)=CC=1CN1CCOCC1 ARBGSRDZYJRBBH-UHFFFAOYSA-N 0.000 claims 2
- ZQUYTFDQRXAHJD-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-hydroxy-3-phenylprop-1-ynyl)-6-(oxan-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C=CC=CC=1C(O)C#CC(C1=NN=C(C(O)=C1C=1)C(=O)NCC=2C=CC(Cl)=CC=2)=CC=1CC1CCOCC1 ZQUYTFDQRXAHJD-UHFFFAOYSA-N 0.000 claims 2
- RNVVOCXGCWKFOC-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-hydroxy-3-phenylpropyl)-6-(oxan-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C=CC=CC=1C(O)CCC(C1=NN=C(C(O)=C1C=1)C(=O)NCC=2C=CC(Cl)=CC=2)=CC=1CC1CCOCC1 RNVVOCXGCWKFOC-UHFFFAOYSA-N 0.000 claims 2
- DXCMWPVHJOPMEX-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(4-hydroxybut-1-ynyl)-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(C#CCCO)=CC=1CN1CCOCC1 DXCMWPVHJOPMEX-UHFFFAOYSA-N 0.000 claims 2
- CARLFBWSKKOMEK-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(4-hydroxybut-1-ynyl)-6-(oxan-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(C#CCCO)=CC=1CC1CCOCC1 CARLFBWSKKOMEK-UHFFFAOYSA-N 0.000 claims 2
- GUAKFLFCKGHMRG-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(5-hydroxypent-1-ynyl)-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(C#CCCCO)=CC=1CN1CCOCC1 GUAKFLFCKGHMRG-UHFFFAOYSA-N 0.000 claims 2
- MWBHOTSDSOEFFS-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(5-hydroxypentyl)-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(CCCCCO)=CC=1CN1CCOCC1 MWBHOTSDSOEFFS-UHFFFAOYSA-N 0.000 claims 2
- ZXPODLQNYIJBIS-MRXNPFEDSA-N n-[(4-chlorophenyl)methyl]-8-[(3r)-3-hydroxybut-1-ynyl]-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(C#C[C@H](O)C)=CC=1CN1CCOCC1 ZXPODLQNYIJBIS-MRXNPFEDSA-N 0.000 claims 2
- SBKWUMFDAIODBT-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[2-(1-hydroxycyclohexyl)ethynyl]-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C1=C2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)N=NC2=C(C#CC2(O)CCCCC2)C=C1CN1CCOCC1 SBKWUMFDAIODBT-UHFFFAOYSA-N 0.000 claims 2
- SPSBQXKGSSONMA-PLTNMMHCSA-N n-[(4-chlorophenyl)methyl]-8-[2-[(1r,2r)-1-hydroxy-2-methylcyclohexyl]ethyl]-6-(oxan-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C[C@@H]1CCCC[C@@]1(O)CCC1=CC(CC2CCOCC2)=CC2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C12 SPSBQXKGSSONMA-PLTNMMHCSA-N 0.000 claims 2
- PYBLAYVFFCYFHC-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(1,1-dioxo-1,4-thiazinan-4-yl)propyl]-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C1=C(CN2CCOCC2)C=C2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)N=NC2=C1CCCN1CCS(=O)(=O)CC1 PYBLAYVFFCYFHC-UHFFFAOYSA-N 0.000 claims 2
- HLCQJXMBWHPZFE-UHFFFAOYSA-N 4-(morpholin-4-ylmethyl)cinnoline-3-carboxamide Chemical compound NC(=O)C1=NN=C2C=CC=CC2=C1CN1CCOCC1 HLCQJXMBWHPZFE-UHFFFAOYSA-N 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- LBEAYDLGLMZOGQ-UHFFFAOYSA-N 8-[3-(carbamoylamino)-3-methylbut-1-ynyl]-n-[(4-chlorophenyl)methyl]-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(C#CC(C)(NC(N)=O)C)=CC=1CN1CCOCC1 LBEAYDLGLMZOGQ-UHFFFAOYSA-N 0.000 claims 1
- LBGQERGEZNQMAT-UHFFFAOYSA-N cinnoline-3-carboxamide Chemical compound C1=CC=C2N=NC(C(=O)N)=CC2=C1 LBGQERGEZNQMAT-UHFFFAOYSA-N 0.000 claims 1
- BJRTYXSZEHGABW-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-6-(oxan-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C1=C2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)N=NC2=CC=C1CC1CCOCC1 BJRTYXSZEHGABW-UHFFFAOYSA-N 0.000 claims 1
- MJRWBAUMLJOQRL-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(2-cyclopropylethyl)-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C1=C(CN2CCOCC2)C=C2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)N=NC2=C1CCC1CC1 MJRWBAUMLJOQRL-UHFFFAOYSA-N 0.000 claims 1
- PFWQAKMIQIPOIG-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(2-cyclopropylethynyl)-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C1=C2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)N=NC2=C(C#CC2CC2)C=C1CN1CCOCC1 PFWQAKMIQIPOIG-UHFFFAOYSA-N 0.000 claims 1
- WCRHFSHCICNKPF-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3,3-dicyclopropyl-3-hydroxypropyl)-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C1=C(CN2CCOCC2)C=C2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)N=NC2=C1CCC(O)(C1CC1)C1CC1 WCRHFSHCICNKPF-UHFFFAOYSA-N 0.000 claims 1
- OIVPFHLNOAZEHK-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-hydroxyprop-1-ynyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound N=1N=C2C(C#CCO)=CC=CC2=C(O)C=1C(=O)NCC1=CC=C(Cl)C=C1 OIVPFHLNOAZEHK-UHFFFAOYSA-N 0.000 claims 1
- LVNULNUQXIYZFV-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-hydroxyprop-1-ynyl)-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(C#CCO)=CC=1CN1CCOCC1 LVNULNUQXIYZFV-UHFFFAOYSA-N 0.000 claims 1
- CFSQISNTTOESHS-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-hydroxyprop-1-ynyl)-6-(oxan-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(C#CCO)=CC=1CC1CCOCC1 CFSQISNTTOESHS-UHFFFAOYSA-N 0.000 claims 1
- FOOPEVRFDORPOI-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-hydroxypropyl)-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(CCCO)=CC=1CN1CCOCC1 FOOPEVRFDORPOI-UHFFFAOYSA-N 0.000 claims 1
- HIOWOXHRWAMTJF-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(3-hydroxypropyl)-6-(oxan-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(CCCO)=CC=1CC1CCOCC1 HIOWOXHRWAMTJF-UHFFFAOYSA-N 0.000 claims 1
- XFDLXIWPKONYTM-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(4-hydroxybut-1-ynyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound N=1N=C2C(C#CCCO)=CC=CC2=C(O)C=1C(=O)NCC1=CC=C(Cl)C=C1 XFDLXIWPKONYTM-UHFFFAOYSA-N 0.000 claims 1
- AETKBJJVPGBBLM-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(4-hydroxybutyl)-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(CCCCO)=CC=1CN1CCOCC1 AETKBJJVPGBBLM-UHFFFAOYSA-N 0.000 claims 1
- RDEKETYSAXPPNL-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-(4-hydroxybutyl)-6-(oxan-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(CCCCO)=CC=1CC1CCOCC1 RDEKETYSAXPPNL-UHFFFAOYSA-N 0.000 claims 1
- ZHWUBLFRLMPKFP-MRXNPFEDSA-N n-[(4-chlorophenyl)methyl]-8-[(3r)-3-hydroxybutyl]-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(CC[C@H](O)C)=CC=1CN1CCOCC1 ZHWUBLFRLMPKFP-MRXNPFEDSA-N 0.000 claims 1
- ZXPODLQNYIJBIS-INIZCTEOSA-N n-[(4-chlorophenyl)methyl]-8-[(3s)-3-hydroxybut-1-ynyl]-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(C#C[C@@H](O)C)=CC=1CN1CCOCC1 ZXPODLQNYIJBIS-INIZCTEOSA-N 0.000 claims 1
- IKQCQKBUSHBWSG-QJWGWKRISA-N n-[(4-chlorophenyl)methyl]-8-[2-[(1r,2r)-1-hydroxy-2-methylcyclohexyl]ethynyl]-6-(oxan-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C[C@@H]1CCCC[C@]1(O)C#CC1=CC(CC2CCOCC2)=CC2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C12 IKQCQKBUSHBWSG-QJWGWKRISA-N 0.000 claims 1
- ZJMNMJCUSHSNFK-YKSBVNFPSA-N n-[(4-chlorophenyl)methyl]-8-[2-[(1r,2s)-2-hydroxycyclopentyl]ethynyl]-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound O[C@H]1CCC[C@@H]1C#CC1=CC(CN2CCOCC2)=CC2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C12 ZJMNMJCUSHSNFK-YKSBVNFPSA-N 0.000 claims 1
- CZQMZCJDLBGTKX-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(1,1-dioxo-1,4-thiazinan-4-yl)prop-1-ynyl]-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C1=C2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)N=NC2=C(C#CCN2CCS(=O)(=O)CC2)C=C1CN1CCOCC1 CZQMZCJDLBGTKX-UHFFFAOYSA-N 0.000 claims 1
- OTPPZJMSNJKLFD-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(4,5-dichloroimidazol-1-yl)prop-1-ynyl]-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C1=C2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)N=NC2=C(C#CCN2C(=C(Cl)N=C2)Cl)C=C1CN1CCOCC1 OTPPZJMSNJKLFD-UHFFFAOYSA-N 0.000 claims 1
- ZQBDEJYXDLWSHR-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(4,5-dichloroimidazol-1-yl)propyl]-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C1=C(CN2CCOCC2)C=C2C(O)=C(C(=O)NCC=3C=CC(Cl)=CC=3)N=NC2=C1CCCN1C=NC(Cl)=C1Cl ZQBDEJYXDLWSHR-UHFFFAOYSA-N 0.000 claims 1
- WPQONQOBDIVEKN-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(dimethylamino)prop-1-ynyl]-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(C#CCN(C)C)=CC=1CN1CCOCC1 WPQONQOBDIVEKN-UHFFFAOYSA-N 0.000 claims 1
- OBAYCZMMRBTYIS-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(dimethylamino)prop-1-ynyl]-6-(oxan-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(C#CCN(C)C)=CC=1CC1CCOCC1 OBAYCZMMRBTYIS-UHFFFAOYSA-N 0.000 claims 1
- REPIEUIKVRUWKI-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(dimethylamino)propyl]-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(CCCN(C)C)=CC=1CN1CCOCC1 REPIEUIKVRUWKI-UHFFFAOYSA-N 0.000 claims 1
- TYHBFTVFKWDGAL-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-(dimethylamino)propyl]-6-(oxan-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C=1C2=C(O)C(C(=O)NCC=3C=CC(Cl)=CC=3)=NN=C2C(CCCN(C)C)=CC=1CC1CCOCC1 TYHBFTVFKWDGAL-UHFFFAOYSA-N 0.000 claims 1
- DZFJHAARFXTFEX-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-methyl-3-(4-sulfanylidene-1,3,5-triazinan-1-yl)but-1-ynyl]-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C1NC(=S)NCN1C(C)(C)C#CC(C1=NN=C(C(O)=C1C=1)C(=O)NCC=2C=CC(Cl)=CC=2)=CC=1CN1CCOCC1 DZFJHAARFXTFEX-UHFFFAOYSA-N 0.000 claims 1
- IJSSRGGLTITSMY-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-[3-methyl-3-(4-sulfanylidene-1,3,5-triazinan-1-yl)butyl]-6-(morpholin-4-ylmethyl)-4-oxo-1h-cinnoline-3-carboxamide Chemical compound C1NC(=S)NCN1C(C)(C)CCC(C1=NN=C(C(O)=C1C=1)C(=O)NCC=2C=CC(Cl)=CC=2)=CC=1CN1CCOCC1 IJSSRGGLTITSMY-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- 201000010099 disease Diseases 0.000 description 6
- 150000001721 carbon Chemical group 0.000 description 5
- 125000006413 ring segment Chemical group 0.000 description 4
- 241001529453 unidentified herpesvirus Species 0.000 description 4
- 230000003612 virological effect Effects 0.000 description 4
- 230000000840 anti-viral effect Effects 0.000 description 3
- 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 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 108010014303 DNA-directed DNA polymerase Proteins 0.000 description 2
- 201000005866 Exanthema Subitum Diseases 0.000 description 2
- 241000701074 Human alphaherpesvirus 2 Species 0.000 description 2
- 241000701041 Human betaherpesvirus 7 Species 0.000 description 2
- 241001502974 Human gammaherpesvirus 8 Species 0.000 description 2
- 241000701027 Human herpesvirus 6 Species 0.000 description 2
- 206010061598 Immunodeficiency Diseases 0.000 description 2
- 208000036485 Roseola Diseases 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 231100000676 disease causative agent Toxicity 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 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 description 1
- 208000011691 Burkitt lymphomas Diseases 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 201000006082 Chickenpox Diseases 0.000 description 1
- 206010008874 Chronic Fatigue Syndrome Diseases 0.000 description 1
- 208000032170 Congenital Abnormalities Diseases 0.000 description 1
- 206010010356 Congenital anomaly Diseases 0.000 description 1
- 108020004414 DNA Proteins 0.000 description 1
- 102000053602 DNA Human genes 0.000 description 1
- 241000450599 DNA viruses Species 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 208000007514 Herpes zoster Diseases 0.000 description 1
- 208000017604 Hodgkin disease Diseases 0.000 description 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 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 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 208000034578 Multiple myelomas Diseases 0.000 description 1
- 208000002454 Nasopharyngeal Carcinoma Diseases 0.000 description 1
- 206010061306 Nasopharyngeal cancer Diseases 0.000 description 1
- 208000037581 Persistent Infection Diseases 0.000 description 1
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 206010065857 Primary Effusion Lymphoma Diseases 0.000 description 1
- 206010038910 Retinitis Diseases 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 241000700584 Simplexvirus Species 0.000 description 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 description 1
- 206010046980 Varicella Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000007698 birth defect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 150000001854 cinnolines Chemical class 0.000 description 1
- 208000010643 digestive system disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 208000018685 gastrointestinal system disease Diseases 0.000 description 1
- 210000004392 genitalia Anatomy 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 201000006747 infectious mononucleosis Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 208000029766 myalgic encephalomeyelitis/chronic fatigue syndrome Diseases 0.000 description 1
- 201000011216 nasopharynx carcinoma Diseases 0.000 description 1
- 230000001613 neoplastic effect Effects 0.000 description 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 102000003390 tumor necrosis factor Human genes 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
-
- 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
- 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)
- Virology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19097600P | 2000-03-21 | 2000-03-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200207543B true ZA200207543B (en) | 2003-12-19 |
Family
ID=22703578
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200207543A ZA200207543B (en) | 2000-03-21 | 2002-09-19 | 4-hydroxycinnoline-3-carboxyamides as antiviral agents. |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6458788B1 (fr) |
| EP (1) | EP1265872A1 (fr) |
| JP (1) | JP2003531195A (fr) |
| KR (1) | KR20020081480A (fr) |
| CN (1) | CN1398258A (fr) |
| AR (1) | AR028269A1 (fr) |
| AU (1) | AU2001243239A1 (fr) |
| BR (1) | BR0109391A (fr) |
| CA (1) | CA2399741A1 (fr) |
| MX (1) | MXPA02009248A (fr) |
| NZ (1) | NZ521521A (fr) |
| WO (1) | WO2001081318A1 (fr) |
| ZA (1) | ZA200207543B (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20060041254A (ko) * | 2003-07-24 | 2006-05-11 | 아스텔라스세이야쿠 가부시키가이샤 | 퀴놀론 유도체 또는 그의 염 |
| US7465795B2 (en) | 2005-12-20 | 2008-12-16 | Astrazeneca Ab | Compounds and uses thereof |
| CA2634305A1 (fr) | 2005-12-20 | 2007-06-28 | Marc Chapdelaine | Derives substitues de la cinnoline en tant que modulateurs du recepteur du gabaa et leur procede de synthese |
| WO2020053654A1 (fr) | 2018-09-12 | 2020-03-19 | Novartis Ag | Composés antiviraux de pyridopyrazinedione |
| KR20220070005A (ko) | 2019-09-26 | 2022-05-27 | 노파르티스 아게 | 항바이러스성 피라졸로피리디논 화합물 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4568649A (en) | 1983-02-22 | 1986-02-04 | Immunex Corporation | Immediate ligand detection assay |
| US4559157A (en) | 1983-04-21 | 1985-12-17 | Creative Products Resource Associates, Ltd. | Cosmetic applicator useful for skin moisturizing |
| LU84979A1 (fr) | 1983-08-30 | 1985-04-24 | Oreal | Composition cosmetique ou pharmaceutique sous forme aqueuse ou anhydre dont la phase grasse contient un polyether oligomere et polyethers oligomeres nouveaux |
| 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 |
| US4820508A (en) | 1987-06-23 | 1989-04-11 | Neutrogena Corporation | Skin protective composition |
| US4992478A (en) | 1988-04-04 | 1991-02-12 | Warner-Lambert Company | Antiinflammatory skin moisturizing composition and method of preparing same |
| US4938949A (en) | 1988-09-12 | 1990-07-03 | University Of New York | Treatment of damaged bone marrow and dosage units therefor |
| WO1997004779A1 (fr) | 1995-08-02 | 1997-02-13 | Chiroscience Limited | Quinolones et leur utilisation therapeutique |
| MX9800921A (es) | 1995-08-02 | 1998-05-31 | Chirotech Technology Ltd | Quinolonas y su uso terapeutico. |
| US6093732A (en) | 1997-12-22 | 2000-07-25 | Pharmacia & Upjohn Company | 4-hydroxyquinoline-3-carboxamides and hydrazides as antiviral agents |
| US6331548B1 (en) | 1998-01-29 | 2001-12-18 | Suntory Limited | 1-cycloalkyl-1,8-naphthyridin-4-one derivative as type IV phosphodiesterase inhibitor |
-
2001
- 2001-03-15 KR KR1020027012467A patent/KR20020081480A/ko not_active Application Discontinuation
- 2001-03-15 BR BR0109391-6A patent/BR0109391A/pt not_active IP Right Cessation
- 2001-03-15 CA CA002399741A patent/CA2399741A1/fr not_active Abandoned
- 2001-03-15 MX MXPA02009248A patent/MXPA02009248A/es unknown
- 2001-03-15 US US09/808,902 patent/US6458788B1/en not_active Expired - Fee Related
- 2001-03-15 EP EP01916182A patent/EP1265872A1/fr not_active Withdrawn
- 2001-03-15 WO PCT/US2001/005807 patent/WO2001081318A1/fr not_active Application Discontinuation
- 2001-03-15 CN CN01804486A patent/CN1398258A/zh active Pending
- 2001-03-15 AU AU2001243239A patent/AU2001243239A1/en not_active Abandoned
- 2001-03-15 JP JP2001578412A patent/JP2003531195A/ja active Pending
- 2001-03-15 NZ NZ521521A patent/NZ521521A/en unknown
- 2001-03-20 AR ARP010101300A patent/AR028269A1/es not_active Application Discontinuation
-
2002
- 2002-09-19 ZA ZA200207543A patent/ZA200207543B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20020042397A1 (en) | 2002-04-11 |
| WO2001081318A1 (fr) | 2001-11-01 |
| NZ521521A (en) | 2004-10-29 |
| BR0109391A (pt) | 2003-06-03 |
| AR028269A1 (es) | 2003-04-30 |
| AU2001243239A1 (en) | 2001-11-07 |
| CN1398258A (zh) | 2003-02-19 |
| CA2399741A1 (fr) | 2001-11-01 |
| JP2003531195A (ja) | 2003-10-21 |
| MXPA02009248A (es) | 2003-03-12 |
| EP1265872A1 (fr) | 2002-12-18 |
| KR20020081480A (ko) | 2002-10-26 |
| US6458788B1 (en) | 2002-10-01 |
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