NZ586695A - TRICYCLIC COMPOUNDS AS MODULATORS OF TNF-alpha SYNTHESIS AND AS PDE4 INHIBITORS - Google Patents

Info

Publication number

NZ586695A

NZ586695A NZ586695A NZ58669509A NZ586695A NZ 586695 A NZ586695 A NZ 586695A NZ 586695 A NZ586695 A NZ 586695A NZ 58669509 A NZ58669509 A NZ 58669509A NZ 586695 A NZ586695 A NZ 586695A

Authority

NZ

New Zealand

Prior art keywords

methoxy

quinoline

pyrimido

dione

chloro

Prior art date

2008-01-25

Links

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 146
• 108060008682 Tumor Necrosis Factor Proteins 0.000 title abstract description 78
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 title abstract description 58
• 230000015572 biosynthetic process Effects 0.000 title description 8
• 238000003786 synthesis reaction Methods 0.000 title description 8
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title description 3
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title description 3
• MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 title description 2
• 238000000034 method Methods 0.000 claims abstract description 272
• 150000003839 salts Chemical class 0.000 claims abstract description 52
• 239000000203 mixture Substances 0.000 claims abstract description 41
• IISWCMIDUMTUPJ-UHFFFAOYSA-N 3-(3-chlorophenyl)-1-(1-ethylsulfonylpiperidin-4-yl)-7-methoxypyrimido[5,4-c]quinoline-2,4-dione Chemical compound C1CN(S(=O)(=O)CC)CCC1N1C(=O)N(C=2C=C(Cl)C=CC=2)C(=O)C2=CN=C3C(OC)=CC=CC3=C21 IISWCMIDUMTUPJ-UHFFFAOYSA-N 0.000 claims abstract description 7
• QBTZSDNOQVLDBB-INIZCTEOSA-N 3-(3-chlorophenyl)-7-methoxy-1-[(3s)-1-methylsulfonylpyrrolidin-3-yl]pyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C=C(Cl)C=CC=1)C1=O)=O)=C2N1[C@H]1CCN(S(C)(=O)=O)C1 QBTZSDNOQVLDBB-INIZCTEOSA-N 0.000 claims abstract description 6
• QBTZSDNOQVLDBB-MRXNPFEDSA-N 3-(3-chlorophenyl)-7-methoxy-1-[(3r)-1-methylsulfonylpyrrolidin-3-yl]pyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C=C(Cl)C=CC=1)C1=O)=O)=C2N1[C@@H]1CCN(S(C)(=O)=O)C1 QBTZSDNOQVLDBB-MRXNPFEDSA-N 0.000 claims abstract description 5
• 239000008194 pharmaceutical composition Substances 0.000 claims description 29
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• 238000003556 assay Methods 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 9
• SUUKGKCXNMAFGK-UHFFFAOYSA-N 1h-pyrimido[5,4-c]quinoline-2,4-dione Chemical compound C1=CC=CC2=NC=C(C(=O)NC(=O)N3)C3=C21 SUUKGKCXNMAFGK-UHFFFAOYSA-N 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• MUQKVPSLHRVESB-UHFFFAOYSA-N 3-(3-chlorophenyl)-7-methoxy-1-(1-methylsulfonylpiperidin-4-yl)pyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C=C(Cl)C=CC=1)C1=O)=O)=C2N1C1CCN(S(C)(=O)=O)CC1 MUQKVPSLHRVESB-UHFFFAOYSA-N 0.000 claims description 7
• 239000012131 assay buffer Substances 0.000 claims description 6
• 125000004494 ethyl ester group Chemical group 0.000 claims description 5
• NMCBQDCTQPGXHQ-UHFFFAOYSA-N 1-cyclopentyl-7-methoxy-3-(3-methylphenyl)pyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C=C(C)C=CC=1)C1=O)=O)=C2N1C1CCCC1 NMCBQDCTQPGXHQ-UHFFFAOYSA-N 0.000 claims description 4
• 101000988419 Homo sapiens cAMP-specific 3',5'-cyclic phosphodiesterase 4D Proteins 0.000 claims description 4
• CTKRVYLHFHYHOK-GOSISDBHSA-N tert-butyl (3r)-3-[3-(3-chlorophenyl)-7-methoxy-2,4-dioxopyrimido[5,4-c]quinolin-1-yl]pyrrolidine-1-carboxylate Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C=C(Cl)C=CC=1)C1=O)=O)=C2N1[C@@H]1CCN(C(=O)OC(C)(C)C)C1 CTKRVYLHFHYHOK-GOSISDBHSA-N 0.000 claims description 4
• 238000002877 time resolved fluorescence resonance energy transfer Methods 0.000 claims description 4
• XBMCCMKXNQMPDO-UHFFFAOYSA-N 1-cyclopentyl-7-methoxy-3-(4-methylthiophen-2-yl)pyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1SC=C(C)C=1)C1=O)=O)=C2N1C1CCCC1 XBMCCMKXNQMPDO-UHFFFAOYSA-N 0.000 claims description 3
• BOWZLOCTDYTWKK-UHFFFAOYSA-N 3-(3-chlorophenyl)-1-cyclohexyl-7-methoxypyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C=C(Cl)C=CC=1)C1=O)=O)=C2N1C1CCCCC1 BOWZLOCTDYTWKK-UHFFFAOYSA-N 0.000 claims description 3
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• YOHPIEBURIBMTH-UHFFFAOYSA-N 3-(2-chlorophenyl)-7-methoxy-1-(1-methylsulfonylpiperidin-4-yl)pyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C(=CC=CC=1)Cl)C1=O)=O)=C2N1C1CCN(S(C)(=O)=O)CC1 YOHPIEBURIBMTH-UHFFFAOYSA-N 0.000 claims description 2
• PEPXWYFVYAYCEQ-HNNXBMFYSA-N 3-(3-chlorophenyl)-7-methoxy-1-[(3s)-pyrrolidin-3-yl]pyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C=C(Cl)C=CC=1)C1=O)=O)=C2N1[C@H]1CCNC1 PEPXWYFVYAYCEQ-HNNXBMFYSA-N 0.000 claims description 2
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• 238000012986 modification Methods 0.000 claims 2
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• PEPXWYFVYAYCEQ-OAHLLOKOSA-N 3-(3-chlorophenyl)-7-methoxy-1-[(3r)-pyrrolidin-3-yl]pyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C=C(Cl)C=CC=1)C1=O)=O)=C2N1[C@@H]1CCNC1 PEPXWYFVYAYCEQ-OAHLLOKOSA-N 0.000 claims 1
• CJIJXIFQYOPWTF-UHFFFAOYSA-N 7-hydroxycoumarin Natural products O1C(=O)C=CC2=CC(O)=CC=C21 CJIJXIFQYOPWTF-UHFFFAOYSA-N 0.000 claims 1
• YKFLJYAKACCWMH-UHFFFAOYSA-N methyl piperidine-1-carboxylate Chemical compound COC(=O)N1CCCCC1 YKFLJYAKACCWMH-UHFFFAOYSA-N 0.000 claims 1
• ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical compound C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 claims 1
• HFTAFOQKODTIJY-UHFFFAOYSA-N umbelliferone Natural products Cc1cc2C=CC(=O)Oc2cc1OCC=CC(C)(C)O HFTAFOQKODTIJY-UHFFFAOYSA-N 0.000 claims 1
• 239000003112 inhibitor Substances 0.000 abstract description 22
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• 229910052760 oxygen Inorganic materials 0.000 abstract description 9
• 230000008569 process Effects 0.000 abstract description 5
• LRZNRQNCOZPCEM-UHFFFAOYSA-N 1-cyclopentyl-7-methoxy-3-(3-methylphenyl)pyrimido[5,4-c]quinoline-2,4-dione 1-cyclopentyl-7-methoxy-3-(4-methylthiophen-2-yl)pyrimido[5,4-c]quinoline-2,4-dione Chemical compound C1(CCCC1)N1C(N(C(C=2C=NC=3C(=CC=CC3C21)OC)=O)C=2C=C(C=CC2)C)=O.C2(CCCC2)N2C(N(C(C=1C=NC=3C(=CC=CC3C12)OC)=O)C=1SC=C(C1)C)=O LRZNRQNCOZPCEM-UHFFFAOYSA-N 0.000 abstract 1
• NFZLXCFMLQBQAJ-UHFFFAOYSA-N 7-methoxy-1-(1-methylsulfonylpiperidin-4-yl)pyrimido[5,4-c]quinoline-2,4-dione Chemical compound CS(=O)(=O)N1CCC(CC1)N1C(NC(C=2C=NC=3C(=CC=CC3C21)OC)=O)=O NFZLXCFMLQBQAJ-UHFFFAOYSA-N 0.000 abstract 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 129
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• -1 alkoxyalkyi Chemical group 0.000 description 74
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• 239000002253 acid Substances 0.000 description 42
• WXHANMOYGBPNMN-UHFFFAOYSA-N ethyl 4-(cyclopentylamino)-8-methoxyquinoline-3-carboxylate Chemical compound CCOC(=O)C1=CN=C2C(OC)=CC=CC2=C1NC1CCCC1 WXHANMOYGBPNMN-UHFFFAOYSA-N 0.000 description 42
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• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 30
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