EA018462B1 - ТРИЦИКЛИЧЕСКИЕ СОЕДИНЕНИЯ КАК МОДУЛЯТОРЫ СИНТЕЗА TNF-α И КАК ИНГИБИТОРЫ PDE4 - Google Patents

Info

Publication number

EA018462B1

EA018462B1 EA201070884A EA201070884A EA018462B1 EA 018462 B1 EA018462 B1 EA 018462B1 EA 201070884 A EA201070884 A EA 201070884A EA 201070884 A EA201070884 A EA 201070884A EA 018462 B1 EA018462 B1 EA 018462B1

Authority

EA

Eurasian Patent Office

Prior art keywords

methoxy

pyrimido

quinoline

dione

chlorophenyl

Prior art date

2008-01-25

Links

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• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 168
• 108060008682 Tumor Necrosis Factor Proteins 0.000 title abstract description 5
• 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 title abstract description 5
• 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 abstract 2
• 238000003786 synthesis reaction Methods 0.000 title description 9
• 230000015572 biosynthetic process Effects 0.000 title description 8
• 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title 1
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title 1
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 26
• -1 propan-2-sulfonyl Chemical group 0.000 claims description 124
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 86
• 150000003839 salts Chemical class 0.000 claims description 53
• YZMVLKJJJCMVGX-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline-2,4-dione Chemical compound C1=CC=C2NC(=O)CC(=O)C2=C1 YZMVLKJJJCMVGX-UHFFFAOYSA-N 0.000 claims description 47
• 125000000217 alkyl group Chemical group 0.000 claims description 20
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 19
• NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 16
• VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims description 8
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 8
• DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 claims description 7
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 7
• 239000003937 drug carrier Substances 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• 229910052736 halogen Inorganic materials 0.000 claims description 6
• 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 5
• 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 description 5
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
• 229910052739 hydrogen Inorganic materials 0.000 claims description 5
• 239000001257 hydrogen Substances 0.000 claims description 5
• UXQHERGWFNFMGT-UHFFFAOYSA-N 1-cyclopentyl-3-(2,3-dimethylphenyl)-7-methoxypyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C(=C(C)C=CC=1)C)C1=O)=O)=C2N1C1CCCC1 UXQHERGWFNFMGT-UHFFFAOYSA-N 0.000 claims description 4
• CSURRMSKKGUPBQ-UHFFFAOYSA-N 1-cyclopentyl-3-(2,5-dimethylphenyl)-7-methoxypyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C(=CC=C(C)C=1)C)C1=O)=O)=C2N1C1CCCC1 CSURRMSKKGUPBQ-UHFFFAOYSA-N 0.000 claims description 4
• XNSUXHIVHKZNQR-UHFFFAOYSA-N 1-cyclopentyl-3-(3,4-dimethylphenyl)-7-methoxypyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C=C(C)C(C)=CC=1)C1=O)=O)=C2N1C1CCCC1 XNSUXHIVHKZNQR-UHFFFAOYSA-N 0.000 claims description 4
• ATMBZUZOUPYZSJ-UHFFFAOYSA-N 1-cyclopentyl-3-(3,5-dimethylphenyl)-7-methoxypyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C=C(C)C=C(C)C=1)C1=O)=O)=C2N1C1CCCC1 ATMBZUZOUPYZSJ-UHFFFAOYSA-N 0.000 claims description 4
• PUVOZFSDIYNDGR-UHFFFAOYSA-N 1-cyclopentyl-3-(3-ethylphenyl)-7-methoxypyrimido[5,4-c]quinoline-2,4-dione Chemical compound CCC1=CC=CC(N2C(C3=CN=C4C(OC)=CC=CC4=C3N(C3CCCC3)C2=O)=O)=C1 PUVOZFSDIYNDGR-UHFFFAOYSA-N 0.000 claims description 4
• LYUZLPVTIXFQQE-UHFFFAOYSA-N 1-cyclopentyl-7-methoxy-3-(2-methylphenyl)pyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C(=CC=CC=1)C)C1=O)=O)=C2N1C1CCCC1 LYUZLPVTIXFQQE-UHFFFAOYSA-N 0.000 claims description 4
• 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
• WEWXZCSTWDNTEE-UHFFFAOYSA-N 1-cyclopentyl-7-methoxy-3-thiophen-2-ylpyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1SC=CC=1)C1=O)=O)=C2N1C1CCCC1 WEWXZCSTWDNTEE-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• JUZPJZSDHMNYSS-UHFFFAOYSA-N 3-(3-chlorophenyl)-1-cyclopentyl-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)=C2N1C1CCCC1 JUZPJZSDHMNYSS-UHFFFAOYSA-N 0.000 claims description 4
• 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 4
• VLSIAPYZDCCBPU-KOMQPUFPSA-N COC1=CC=CC2=C1N=CC(C(N(C=1C=C(Cl)C=CC=1)C1=O)=O)=C2N1[C@H]1CC[C@H](C(O)=O)CC1 Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C=C(Cl)C=CC=1)C1=O)=O)=C2N1[C@H]1CC[C@H](C(O)=O)CC1 VLSIAPYZDCCBPU-KOMQPUFPSA-N 0.000 claims description 4
• JJOYCHKVKWDMEA-UHFFFAOYSA-N ethyl cyclohexanecarboxylate Chemical compound CCOC(=O)C1CCCCC1 JJOYCHKVKWDMEA-UHFFFAOYSA-N 0.000 claims description 4
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
• BHEJVSJTYQYCBB-UHFFFAOYSA-N 1-cyclopentyl-3-(3-fluorophenyl)-7-methoxypyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C=C(F)C=CC=1)C1=O)=O)=C2N1C1CCCC1 BHEJVSJTYQYCBB-UHFFFAOYSA-N 0.000 claims description 3
• NLIFNZBMILAJFA-UHFFFAOYSA-N 1-cyclopentyl-3-(4-fluoro-3-methylphenyl)-7-methoxypyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C=C(C)C(F)=CC=1)C1=O)=O)=C2N1C1CCCC1 NLIFNZBMILAJFA-UHFFFAOYSA-N 0.000 claims description 3
• FOCBXVWTIKRGEO-UHFFFAOYSA-N 1-cyclopentyl-7-methoxy-3-(4-methylphenyl)pyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C=CC(C)=CC=1)C1=O)=O)=C2N1C1CCCC1 FOCBXVWTIKRGEO-UHFFFAOYSA-N 0.000 claims description 3
• RTYXYVDCINKRTD-UHFFFAOYSA-N 1-cyclopentyl-7-methoxy-3-[5-methyl-2-(trifluoromethyl)furan-3-yl]pyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C1=C(OC(C)=C1)C(F)(F)F)C1=O)=O)=C2N1C1CCCC1 RTYXYVDCINKRTD-UHFFFAOYSA-N 0.000 claims description 3
• RSCKXYMEBLRFKV-UHFFFAOYSA-N 1-cyclopentyl-7-methoxy-3-phenylpyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C=CC=CC=1)C1=O)=O)=C2N1C1CCCC1 RSCKXYMEBLRFKV-UHFFFAOYSA-N 0.000 claims description 3
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• 125000002541 furyl group Chemical group 0.000 claims description 3
• YKFLJYAKACCWMH-UHFFFAOYSA-N methyl piperidine-1-carboxylate Chemical compound COC(=O)N1CCCCC1 YKFLJYAKACCWMH-UHFFFAOYSA-N 0.000 claims description 3
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
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• 125000001544 thienyl group Chemical group 0.000 claims description 3
• OOUYBBSDYRMPDH-UHFFFAOYSA-N 1-cyclopentyl-3-(3-fluoro-4-methylphenyl)-7-methoxypyrimido[5,4-c]quinoline-2,4-dione Chemical compound COC1=CC=CC2=C1N=CC(C(N(C=1C=C(F)C(C)=CC=1)C1=O)=O)=C2N1C1CCCC1 OOUYBBSDYRMPDH-UHFFFAOYSA-N 0.000 claims description 2
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• 125000001188 haloalkyl group Chemical group 0.000 claims description 2
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