JP2009533427A5 - - Google Patents
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- JP2009533427A5 JP2009533427A5 JP2009505326A JP2009505326A JP2009533427A5 JP 2009533427 A5 JP2009533427 A5 JP 2009533427A5 JP 2009505326 A JP2009505326 A JP 2009505326A JP 2009505326 A JP2009505326 A JP 2009505326A JP 2009533427 A5 JP2009533427 A5 JP 2009533427A5
- Authority
- JP
- Japan
- Prior art keywords
- thioxo
- tetrahydro
- purin
- methyl
- amino
- 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.)
- Ceased
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- 239000000203 mixture Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 15
- 229910052717 sulfur Inorganic materials 0.000 claims 14
- 150000003839 salts Chemical class 0.000 claims 13
- 125000003545 alkoxy group Chemical group 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 150000002367 halogens Chemical class 0.000 claims 12
- 229920006395 saturated elastomer Polymers 0.000 claims 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 10
- 239000012453 solvate Substances 0.000 claims 8
- 125000002950 monocyclic group Chemical group 0.000 claims 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 239000001301 oxygen Substances 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 4
- 239000002671 adjuvant Substances 0.000 claims 3
- 239000003085 diluting agent Substances 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- -1 5-methylpyrazin-2-yl Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- HNUHQXANZGQWGQ-UHFFFAOYSA-N 2-sulfanylidene-3-[2-(2h-triazol-4-ylmethylamino)propyl]-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CN=NN1 HNUHQXANZGQWGQ-UHFFFAOYSA-N 0.000 claims 1
- YVQCDZWXMRZDNJ-UHFFFAOYSA-N 3-(1h-benzimidazol-2-ylmethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2NC(CN3C(=S)NC(C=4NC=NC=43)=O)=NC2=C1 YVQCDZWXMRZDNJ-UHFFFAOYSA-N 0.000 claims 1
- MAQKUFVZHSCAGH-UHFFFAOYSA-N 3-(1h-pyrazol-5-ylmethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC=1C=CNN=1 MAQKUFVZHSCAGH-UHFFFAOYSA-N 0.000 claims 1
- IIIADLWTNVXNBD-UHFFFAOYSA-N 3-(2-aminopropyl)-2-sulfanylidene-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.O=C1NC(=S)N(CC(N)C)C2=C1NC=N2 IIIADLWTNVXNBD-UHFFFAOYSA-N 0.000 claims 1
- MYYPRTCFPDGPGK-UHFFFAOYSA-N 3-(2-phenyl-2-pyridin-2-ylethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C=1N=CC=CC=1)C1=CC=CC=C1 MYYPRTCFPDGPGK-UHFFFAOYSA-N 0.000 claims 1
- XOQCUPGBGQMLQK-UHFFFAOYSA-N 3-(pyridin-2-ylmethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC1=CC=CC=N1 XOQCUPGBGQMLQK-UHFFFAOYSA-N 0.000 claims 1
- AHKFFPZJELSEDV-UHFFFAOYSA-N 3-(pyridin-3-ylmethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC1=CC=CN=C1 AHKFFPZJELSEDV-UHFFFAOYSA-N 0.000 claims 1
- UZWAFZKSLZCFRV-UHFFFAOYSA-N 3-(pyridin-4-ylmethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC1=CC=NC=C1 UZWAFZKSLZCFRV-UHFFFAOYSA-N 0.000 claims 1
- AMZQGGBZPWAFRK-UHFFFAOYSA-N 3-(quinolin-4-ylmethyl)-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2C(CN3C(=S)NC(C=4NC=NC=43)=O)=CC=NC2=C1 AMZQGGBZPWAFRK-UHFFFAOYSA-N 0.000 claims 1
- SCYILAUVHGNMOS-UHFFFAOYSA-N 3-[(1-methylindol-2-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2N(C)C(CN3C(NC(=O)C=4NC=NC=43)=S)=CC2=C1 SCYILAUVHGNMOS-UHFFFAOYSA-N 0.000 claims 1
- WYPCJTAXRKLCNR-UHFFFAOYSA-N 3-[(2-butyl-4-chloro-1h-imidazol-5-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound N1C(CCCC)=NC(Cl)=C1CN1C(=S)NC(=O)C2=C1N=CN2 WYPCJTAXRKLCNR-UHFFFAOYSA-N 0.000 claims 1
- ILPHIXRPMGQFJZ-UHFFFAOYSA-N 3-[(3,5-dimethyl-1,2-oxazol-4-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound CC1=NOC(C)=C1CN1C(=S)NC(=O)C2=C1N=CN2 ILPHIXRPMGQFJZ-UHFFFAOYSA-N 0.000 claims 1
- HVYDXNSLQRFDIG-UHFFFAOYSA-N 3-[(3-butoxypyridin-2-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound CCCCOC1=CC=CN=C1CN1C(=S)NC(=O)C2=C1N=CN2 HVYDXNSLQRFDIG-UHFFFAOYSA-N 0.000 claims 1
- GSEOEHAWXVFUCX-UHFFFAOYSA-N 3-[(3-propan-2-yl-1,2-oxazol-5-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound O1N=C(C(C)C)C=C1CN1C(=S)NC(=O)C2=C1N=CN2 GSEOEHAWXVFUCX-UHFFFAOYSA-N 0.000 claims 1
- XXICVNQMYQJXLB-UHFFFAOYSA-N 3-[(4-butoxypyridin-2-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound CCCCOC1=CC=NC(CN2C(NC(=O)C=3NC=NC=32)=S)=C1 XXICVNQMYQJXLB-UHFFFAOYSA-N 0.000 claims 1
- QQPMWNAWGBKGCU-UHFFFAOYSA-N 3-[(4-fluoro-1h-indol-3-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2C(F)=CC=CC=2NC=C1CN(C(NC1=O)=S)C2=C1NC=N2 QQPMWNAWGBKGCU-UHFFFAOYSA-N 0.000 claims 1
- JUHNYHJKAXOZNQ-UHFFFAOYSA-N 3-[(4-methyl-1,2,5-oxadiazol-3-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound CC1=NON=C1CN1C(=S)NC(=O)C2=C1N=CN2 JUHNYHJKAXOZNQ-UHFFFAOYSA-N 0.000 claims 1
- SXNNLWVBOSOYAT-UHFFFAOYSA-N 3-[(5-chloro-1h-indol-3-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C12=CC(Cl)=CC=C2NC=C1CN(C(NC1=O)=S)C2=C1NC=N2 SXNNLWVBOSOYAT-UHFFFAOYSA-N 0.000 claims 1
- NLEUINUWQPGXHI-UHFFFAOYSA-N 3-[(5-fluoro-1h-indol-2-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C=1C2=CC(F)=CC=C2NC=1CN(C(NC1=O)=S)C2=C1NC=N2 NLEUINUWQPGXHI-UHFFFAOYSA-N 0.000 claims 1
- FCYBVAXJKFBGAG-UHFFFAOYSA-N 3-[(6-butoxypyridin-2-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound CCCCOC1=CC=CC(CN2C(NC(=O)C=3NC=NC=32)=S)=N1 FCYBVAXJKFBGAG-UHFFFAOYSA-N 0.000 claims 1
- ZBDZGNKVUOCITH-UHFFFAOYSA-N 3-[(6-phenoxypyridin-3-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C=N1)=CC=C1OC1=CC=CC=C1 ZBDZGNKVUOCITH-UHFFFAOYSA-N 0.000 claims 1
- BFIWTKIXULBUTE-UHFFFAOYSA-N 3-[1-(1h-benzimidazol-2-yl)ethyl]-2-sulfanylidene-7h-purin-6-one Chemical compound N=1C2=CC=CC=C2NC=1C(C)N(C(NC1=O)=S)C2=C1NC=N2 BFIWTKIXULBUTE-UHFFFAOYSA-N 0.000 claims 1
- KHHYBTYRTYJWQL-UHFFFAOYSA-N 3-[2-(1h-benzimidazol-2-yl)ethyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2NC(CCN3C(=S)NC(C=4NC=NC=43)=O)=NC2=C1 KHHYBTYRTYJWQL-UHFFFAOYSA-N 0.000 claims 1
- XPJXEVNLVLNQRN-UHFFFAOYSA-N 3-[2-(1h-benzimidazol-2-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2NC(CNC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=NC2=C1 XPJXEVNLVLNQRN-UHFFFAOYSA-N 0.000 claims 1
- VQQXXEBNSFHZEL-UHFFFAOYSA-N 3-[2-(1h-imidazol-2-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=NC=CN1 VQQXXEBNSFHZEL-UHFFFAOYSA-N 0.000 claims 1
- VPIIFTJWQLSYIL-UHFFFAOYSA-N 3-[2-(pyridin-2-ylmethoxy)propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)OCC1=CC=CC=N1 VPIIFTJWQLSYIL-UHFFFAOYSA-N 0.000 claims 1
- ATPOLLKTGMVGBH-UHFFFAOYSA-N 3-[2-(pyridin-2-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=CC=N1 ATPOLLKTGMVGBH-UHFFFAOYSA-N 0.000 claims 1
- RRQORCIDUZXJPT-UHFFFAOYSA-N 3-[2-(pyridin-3-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=CN=C1 RRQORCIDUZXJPT-UHFFFAOYSA-N 0.000 claims 1
- YMEBQHCQKRPKCI-UHFFFAOYSA-N 3-[2-(pyridin-4-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=NC=C1 YMEBQHCQKRPKCI-UHFFFAOYSA-N 0.000 claims 1
- SKAUBHPJNDJLBF-UHFFFAOYSA-N 3-[2-(quinolin-2-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=CC=CC2=NC(CNC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=CC=C21 SKAUBHPJNDJLBF-UHFFFAOYSA-N 0.000 claims 1
- DYKYDXGYDOPQCH-UHFFFAOYSA-N 3-[2-(quinolin-3-ylmethylamino)propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=CC2=CC(CNC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=CN=C21 DYKYDXGYDOPQCH-UHFFFAOYSA-N 0.000 claims 1
- FZDOSCHSMNDEKZ-UHFFFAOYSA-N 3-[2-(quinolin-4-ylmethylamino)ethyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2C(CNCCN3C(=S)NC(C=4NC=NC=43)=O)=CC=NC2=C1 FZDOSCHSMNDEKZ-UHFFFAOYSA-N 0.000 claims 1
- ZIDMKBGVDCBFNB-UHFFFAOYSA-N 3-[2-[(1-methylimidazol-2-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=NC=CN1C ZIDMKBGVDCBFNB-UHFFFAOYSA-N 0.000 claims 1
- CKBADCZMJZPWOE-UHFFFAOYSA-N 3-[2-[(1-methylindol-3-yl)methylamino]ethyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C12=CC=CC=C2N(C)C=C1CNCCN1C(=S)NC(=O)C2=C1N=CN2 CKBADCZMJZPWOE-UHFFFAOYSA-N 0.000 claims 1
- RSEFPWXFDKRGNQ-UHFFFAOYSA-N 3-[2-[(1-methylindol-3-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2C(CNC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=CN(C)C2=C1 RSEFPWXFDKRGNQ-UHFFFAOYSA-N 0.000 claims 1
- HJJAUEDOGPHQPS-UHFFFAOYSA-N 3-[2-[(1-methylpyrrol-2-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=CN1C HJJAUEDOGPHQPS-UHFFFAOYSA-N 0.000 claims 1
- CCNVCEPQJBXJJV-UHFFFAOYSA-N 3-[2-[(1-tert-butyl-3,5-dimethylpyrazol-4-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC=1C(C)=NN(C(C)(C)C)C=1C CCNVCEPQJBXJJV-UHFFFAOYSA-N 0.000 claims 1
- URTIWUIHHQAMGU-UHFFFAOYSA-N 3-[2-[(4,6-dichloropyrimidin-5-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=C(Cl)N=CN=C1Cl URTIWUIHHQAMGU-UHFFFAOYSA-N 0.000 claims 1
- ZKKGDXCJLITGDO-UHFFFAOYSA-N 3-[2-[(5-bromo-3-methylimidazol-4-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=C(Br)N=CN1C ZKKGDXCJLITGDO-UHFFFAOYSA-N 0.000 claims 1
- NVMLJGAILCBLQF-UHFFFAOYSA-N 3-[2-[(6-bromo-2-methylimidazo[1,2-a]pyridin-3-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC(Br)=CN2C(CNC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=C(C)N=C21 NVMLJGAILCBLQF-UHFFFAOYSA-N 0.000 claims 1
- ZIWMBSQQYYREIU-UHFFFAOYSA-N 3-[2-[(6-chloropyridin-3-yl)methylamino]propyl]-2-sulfanylidene-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=C(Cl)N=C1 ZIWMBSQQYYREIU-UHFFFAOYSA-N 0.000 claims 1
- FKZCBBOOFJXZIX-UHFFFAOYSA-N 3-[2-[[1-(3-methoxyphenyl)pyrrol-2-yl]methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound COC1=CC=CC(N2C(=CC=C2)CNC(C)CN2C(NC(=O)C=3NC=NC=32)=S)=C1 FKZCBBOOFJXZIX-UHFFFAOYSA-N 0.000 claims 1
- VGLYDQGVKGRCMJ-UHFFFAOYSA-N 3-[2-[[1-(4-butan-2-ylphenyl)pyrrol-2-yl]methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC(C(C)CC)=CC=C1N1C(CNC(C)CN2C(NC(=O)C=3NC=NC=32)=S)=CC=C1 VGLYDQGVKGRCMJ-UHFFFAOYSA-N 0.000 claims 1
- JGFLDGKYQKHBKO-UHFFFAOYSA-N 3-[2-[[1-(4-methylphenyl)sulfonylpyrrol-2-yl]methylamino]propyl]-2-sulfanylidene-7h-purin-6-one;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CC=CN1S(=O)(=O)C1=CC=C(C)C=C1 JGFLDGKYQKHBKO-UHFFFAOYSA-N 0.000 claims 1
- XJUIKKDOXAEZIF-UHFFFAOYSA-N 3-[2-[[1-[2-(2-methoxyphenoxy)ethyl]pyrrol-2-yl]methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound COC1=CC=CC=C1OCCN1C(CNC(C)CN2C(NC(=O)C=3NC=NC=32)=S)=CC=C1 XJUIKKDOXAEZIF-UHFFFAOYSA-N 0.000 claims 1
- KFZWPCHWGYQNRM-UHFFFAOYSA-N 3-[2-[[2-(dimethylamino)pyrimidin-5-yl]methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC1=CN=C(N(C)C)N=C1 KFZWPCHWGYQNRM-UHFFFAOYSA-N 0.000 claims 1
- RUYCBGLQUYCAEG-UHFFFAOYSA-N 3-[2-[[4-(3-chlorobenzoyl)-1-methylpyrrol-2-yl]methylamino]propyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NCC(N(C=1)C)=CC=1C(=O)C1=CC=CC(Cl)=C1 RUYCBGLQUYCAEG-UHFFFAOYSA-N 0.000 claims 1
- DSOXIQGGJIBKDX-UHFFFAOYSA-N 3-[2-[methyl(quinolin-4-ylmethyl)amino]ethyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=CC=C2C(CN(CCN3C(NC(=O)C=4NC=NC=43)=S)C)=CC=NC2=C1 DSOXIQGGJIBKDX-UHFFFAOYSA-N 0.000 claims 1
- WEKREWHBVCUSJN-UHFFFAOYSA-N 3-[[3-ethoxy-4-(2-ethoxyethoxy)pyridin-2-yl]methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound CCOCCOC1=CC=NC(CN2C(NC(=O)C=3NC=NC=32)=S)=C1OCC WEKREWHBVCUSJN-UHFFFAOYSA-N 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 201000003883 Cystic fibrosis Diseases 0.000 claims 1
- 206010014561 Emphysema Diseases 0.000 claims 1
- 102000004190 Enzymes Human genes 0.000 claims 1
- 108090000790 Enzymes Proteins 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 230000009286 beneficial effect Effects 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 201000009267 bronchiectasis Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
- 125000002541 furyl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- DSUIOKUNQXSQHF-UHFFFAOYSA-N n-[1-(6-oxo-2-sulfanylidene-7h-purin-3-yl)propan-2-yl]-1,8-naphthyridine-2-carboxamide Chemical compound C1=CC=NC2=NC(C(=O)NC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=CC=C21 DSUIOKUNQXSQHF-UHFFFAOYSA-N 0.000 claims 1
- CCIWNVVVKVZFGZ-UHFFFAOYSA-N n-[1-(6-oxo-2-sulfanylidene-7h-purin-3-yl)propan-2-yl]-1h-imidazole-2-carboxamide;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NC(=O)C1=NC=CN1 CCIWNVVVKVZFGZ-UHFFFAOYSA-N 0.000 claims 1
- SMBFHTPOCAIXGA-UHFFFAOYSA-N n-[1-(6-oxo-2-sulfanylidene-7h-purin-3-yl)propan-2-yl]pyridine-2-carboxamide Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NC(=O)C1=CC=CC=N1 SMBFHTPOCAIXGA-UHFFFAOYSA-N 0.000 claims 1
- GSLCARCSLQLGFD-UHFFFAOYSA-N n-[1-(6-oxo-2-sulfanylidene-7h-purin-3-yl)propan-2-yl]pyridine-3-carboxamide Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NC(=O)C1=CC=CN=C1 GSLCARCSLQLGFD-UHFFFAOYSA-N 0.000 claims 1
- KIVNADZCPIUYGU-UHFFFAOYSA-N n-[1-(6-oxo-2-sulfanylidene-7h-purin-3-yl)propan-2-yl]pyridine-4-carboxamide Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NC(=O)C1=CC=NC=C1 KIVNADZCPIUYGU-UHFFFAOYSA-N 0.000 claims 1
- KCYZTORODXQMMU-UHFFFAOYSA-N n-[1-(6-oxo-2-sulfanylidene-7h-purin-3-yl)propan-2-yl]pyrimidine-2-carboxamide Chemical compound C1=2N=CNC=2C(=O)NC(=S)N1CC(C)NC(=O)C1=NC=CC=N1 KCYZTORODXQMMU-UHFFFAOYSA-N 0.000 claims 1
- CVVVWYUXSNNDLD-UHFFFAOYSA-N n-[1-(6-oxo-2-sulfanylidene-7h-purin-3-yl)propan-2-yl]quinoline-2-carboxamide Chemical compound C1=CC=CC2=NC(C(=O)NC(CN3C(NC(=O)C=4NC=NC=43)=S)C)=CC=C21 CVVVWYUXSNNDLD-UHFFFAOYSA-N 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
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| AR039385A1 (es) * | 2002-04-19 | 2005-02-16 | Astrazeneca Ab | Derivados de tioxantina como inhibidores de la mieloperoxidasa |
| MY140748A (en) | 2004-12-06 | 2010-01-15 | Astrazeneca Ab | Novel pyrrolo [3,2-d] pyrimidin-4-one derivatives and their use in therapy |
| WO2007120097A1 (en) * | 2006-04-13 | 2007-10-25 | Astrazeneca Ab | Thioxanthine derivatives and their use as inhibitors of mpo |
| TW200804383A (en) * | 2006-06-05 | 2008-01-16 | Astrazeneca Ab | New compounds |
| AR066936A1 (es) * | 2007-06-13 | 2009-09-23 | Astrazeneca Ab | 3 - (2r - tetrahidrofuril - metil) - 2 - tioxantina. composiciones farmaceuticas. |
| US20090053176A1 (en) * | 2007-08-23 | 2009-02-26 | Astrazeneca Ab | New Combination 937 |
| US20090054468A1 (en) * | 2007-08-23 | 2009-02-26 | Astrazeneca Ab | New Use 938 |
| WO2010068171A1 (en) * | 2008-12-12 | 2010-06-17 | Astrazeneca Ab | A process for the preparation of 3- [ (2r) tetrahydrofuran-2- ylmethyl] -2-thioxo-l, 2, 3, 7-tetrahydro-6h-purin-6-one |
| GB0913345D0 (en) | 2009-07-31 | 2009-09-16 | Astrazeneca Ab | New combination 802 |
| WO2011061527A1 (en) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases |
| GB201021992D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | Compound |
| GB201021979D0 (en) | 2010-12-23 | 2011-02-02 | Astrazeneca Ab | New compound |
| CA2853024C (en) | 2011-11-11 | 2017-08-22 | Pfizer Inc. | 2-thiopyrimidinones |
| EP2831076B1 (en) * | 2012-03-29 | 2016-05-25 | Basf Se | N-substituted hetero-bicyclic compounds and derivatives for combating animal pests ii |
| US20170247343A1 (en) | 2014-09-11 | 2017-08-31 | Bristol-Myers Squibb Company | Thioether triazolopyridine and triazolopyrimidine inhibitors of myeloperoxidase |
| US9616063B2 (en) | 2014-12-01 | 2017-04-11 | Astrazeneca Ab | 1-[2-(aminomethyl)benzyl]-2-thioxo-1,2,3,5-tetrahydro-4H-pyrrolo[3,2-d]pyrimidin-4-ones as inhibitors of myeloperoxidase |
| JP2018515480A (ja) | 2015-05-05 | 2018-06-14 | ファイザー・インク | ２−チオピリミジノン |
| US10316035B2 (en) | 2015-09-03 | 2019-06-11 | Bristol-Myers Squibb Company | Triazolopyridine inhibitors of myeloperoxidase |
| US11059818B2 (en) * | 2016-03-14 | 2021-07-13 | Bristol-Myers Squibb Company | Triazolopyridine inhibitors of myeloperoxidase |
| CN115403584B (zh) * | 2021-05-26 | 2024-04-02 | 长春金赛药业有限责任公司 | 2-硫代-2,3-二氢嘧啶-4-酮衍生物、药物组合物及其制备方法和应用 |
| US20240166642A1 (en) | 2022-08-18 | 2024-05-23 | Astrazeneca Ab | Inhibitors of myeloperoxidase |
| WO2025172474A1 (en) | 2024-02-15 | 2025-08-21 | Astrazeneca Ab | Inhibitors of myeloperoxidase |
| WO2025190901A1 (en) | 2024-03-13 | 2025-09-18 | Institut National de la Santé et de la Recherche Médicale | Use of myeloperoxidase (mpo) inhibitors for promoting cd8+ t cell responses |
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| GB9312853D0 (en) * | 1993-06-22 | 1993-08-04 | Euro Celtique Sa | Chemical compounds |
| WO1995002604A1 (en) * | 1993-07-13 | 1995-01-26 | The United States Of America, Represented By The Secretary, Department Of Health And Human Services | A3 adenosine receptor agonists |
| US5708009A (en) * | 1993-12-21 | 1998-01-13 | Eli Lilly And Company | Methods of inhibiting myeloperoxidase activity |
| US6780865B1 (en) * | 1994-02-18 | 2004-08-24 | Cell Therapeutics, Inc. | Compounds having selective hydrolytic potentials |
| US6066641A (en) * | 1994-12-13 | 2000-05-23 | Euro-Celtique S.A. | Aryl thioxanthines |
| ES2264210T3 (es) * | 1997-09-05 | 2006-12-16 | Kyowa Hakko Kogyo Co., Ltd. | Derivados de xantina para el tratamiento de la isquemia cerebral. |
| JP2002541078A (ja) * | 1999-04-02 | 2002-12-03 | ユーロ−セルティーク，エス．エー． | ホスホジエステラーゼｉｖ阻害活性を有するプリン誘導体 |
| AR039385A1 (es) * | 2002-04-19 | 2005-02-16 | Astrazeneca Ab | Derivados de tioxantina como inhibidores de la mieloperoxidasa |
| SE0302756D0 (sv) * | 2003-10-17 | 2003-10-17 | Astrazeneca Ab | Novel Compounds |
| MY140748A (en) * | 2004-12-06 | 2010-01-15 | Astrazeneca Ab | Novel pyrrolo [3,2-d] pyrimidin-4-one derivatives and their use in therapy |
| WO2007120097A1 (en) * | 2006-04-13 | 2007-10-25 | Astrazeneca Ab | Thioxanthine derivatives and their use as inhibitors of mpo |
| TW200804383A (en) * | 2006-06-05 | 2008-01-16 | Astrazeneca Ab | New compounds |
| US20090054468A1 (en) * | 2007-08-23 | 2009-02-26 | Astrazeneca Ab | New Use 938 |
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2007
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- 2007-04-10 TW TW096112534A patent/TW200806667A/zh unknown
- 2007-04-12 KR KR1020087027662A patent/KR20080109087A/ko not_active Withdrawn
- 2007-04-12 JP JP2009505326A patent/JP2009533427A/ja not_active Ceased
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- 2007-04-12 WO PCT/SE2007/000349 patent/WO2007120098A1/en not_active Ceased
- 2007-04-12 US US12/295,306 patent/US8026244B2/en not_active Expired - Fee Related
- 2007-04-12 MX MX2008013033A patent/MX2008013033A/es not_active Application Discontinuation
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- 2007-04-12 AR ARP070101557A patent/AR060429A1/es unknown
- 2007-04-12 AU AU2007239147A patent/AU2007239147A1/en not_active Abandoned
- 2007-04-12 CL CL200701042A patent/CL2007001042A1/es unknown
- 2007-04-12 CA CA002649150A patent/CA2649150A1/en not_active Abandoned
- 2007-04-12 BR BRPI0711529-6A patent/BRPI0711529A2/pt not_active IP Right Cessation
- 2007-04-12 CN CNA200780022184XA patent/CN101466712A/zh active Pending
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2008
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- 2008-09-25 KR KR1020097014335A patent/KR20090109087A/ko not_active Ceased
- 2008-10-14 EC EC2008008821A patent/ECSP088821A/es unknown
- 2008-11-11 NO NO20084764A patent/NO20084764L/no not_active Application Discontinuation
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