KR20080109087A - 티오크산틴 유도체 및 ｍｐｏ 억제제로서의 그의 용도 - Google Patents

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Publication number

KR20080109087A

KR20080109087A KR1020087027662A KR20087027662A KR20080109087A KR 20080109087 A KR20080109087 A KR 20080109087A KR 1020087027662 A KR1020087027662 A KR 1020087027662A KR 20087027662 A KR20087027662 A KR 20087027662A KR 20080109087 A KR20080109087 A KR 20080109087A

Authority

KR

South Korea

Prior art keywords

alkoxy

alkyl

phenoxy

methyl

tetrahydro

Prior art date

2006-04-13

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.)

Withdrawn

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• 239000003112 inhibitor Substances 0.000 title abstract description 8
• 150000001875 compounds Chemical class 0.000 claims abstract description 367
• 150000003839 salts Chemical class 0.000 claims abstract description 57
• 238000000034 method Methods 0.000 claims abstract description 42
• 238000011282 treatment Methods 0.000 claims abstract description 30
• 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 21
• 230000002265 prevention Effects 0.000 claims abstract description 14
• 102000004190 Enzymes Human genes 0.000 claims abstract description 11
• 108090000790 Enzymes Proteins 0.000 claims abstract description 11
• 208000036110 Neuroinflammatory disease Diseases 0.000 claims abstract description 10
• 208000005764 Peripheral Arterial Disease Diseases 0.000 claims abstract description 8
• 208000023504 respiratory system disease Diseases 0.000 claims abstract description 8
• 125000003545 alkoxy group Chemical group 0.000 claims description 214
• 125000000217 alkyl group Chemical group 0.000 claims description 185
• 229910052760 oxygen Inorganic materials 0.000 claims description 177
• 229910052717 sulfur Inorganic materials 0.000 claims description 165
• 229920006395 saturated elastomer Polymers 0.000 claims description 159
• 229910052736 halogen Inorganic materials 0.000 claims description 156
• 150000002367 halogens Chemical class 0.000 claims description 156
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 151
• 125000003118 aryl group Chemical group 0.000 claims description 124
• 229910052757 nitrogen Inorganic materials 0.000 claims description 104
• 125000005842 heteroatom Chemical group 0.000 claims description 86
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 82
• 229910052799 carbon Inorganic materials 0.000 claims description 81
• 125000004429 atom Chemical group 0.000 claims description 66
• 125000002950 monocyclic group Chemical group 0.000 claims description 64
• -1 3-[(4-fluoro-1 H -indol-3-yl) methyl] -2-thioxo-1,2,3,7-tetrahydro-6 H -purin-6-one Phosphorus Chemical compound 0.000 claims description 58
• 125000001424 substituent group Chemical group 0.000 claims description 52
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 50
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 43
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 40
• 229910052739 hydrogen Inorganic materials 0.000 claims description 40
• 125000004122 cyclic group Chemical group 0.000 claims description 39
• 239000001257 hydrogen Substances 0.000 claims description 37
• 125000001072 heteroaryl group Chemical group 0.000 claims description 36
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 33
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 32
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 32
• 239000000460 chlorine Substances 0.000 claims description 32
• 239000001301 oxygen Substances 0.000 claims description 32
• 201000010099 disease Diseases 0.000 claims description 31
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 30
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 29
• 229910052731 fluorine Inorganic materials 0.000 claims description 27
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 26
• 201000006417 multiple sclerosis Diseases 0.000 claims description 25
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
• 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 19
• 239000012453 solvate Substances 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 18
• 150000002431 hydrogen Chemical class 0.000 claims description 17
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 14
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
• SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 14
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 12
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
• SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 12
• 238000004519 manufacturing process Methods 0.000 claims description 12
• 208000018737 Parkinson disease Diseases 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 8
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 8
• VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 claims description 7
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
• 206010019280 Heart failures Diseases 0.000 claims description 7
• 208000030831 Peripheral arterial occlusive disease Diseases 0.000 claims description 7
• 239000011737 fluorine Substances 0.000 claims description 7
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 7
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 7
• FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims description 6
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 6
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 6
• 239000002671 adjuvant Substances 0.000 claims description 6
• 230000009286 beneficial effect Effects 0.000 claims description 6
• 239000003085 diluting agent Substances 0.000 claims description 6
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 6
• 208000015181 infectious disease Diseases 0.000 claims description 6
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 150000003852 triazoles Chemical class 0.000 claims description 6
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 125000002541 furyl group Chemical group 0.000 claims description 5
• WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims description 5
• 230000008569 process Effects 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• 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 description 4
• 201000003883 Cystic fibrosis Diseases 0.000 claims description 4
• WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
• 206010006451 bronchitis Diseases 0.000 claims description 4
• 150000002244 furazanes Chemical class 0.000 claims description 4
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
• WIOYFBDCQDDCTI-UHFFFAOYSA-N 2-sulfanylidene-3-[2-[[6-(trifluoromethyl)pyridin-3-yl]methylamino]propyl]-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(C(F)(F)F)N=C1 WIOYFBDCQDDCTI-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
• 206010065563 Eosinophilic bronchitis Diseases 0.000 claims description 3
• 201000009267 bronchiectasis Diseases 0.000 claims description 3
• 125000001041 indolyl group Chemical group 0.000 claims description 3
• 230000002458 infectious effect Effects 0.000 claims description 3
• 208000027866 inflammatory disease Diseases 0.000 claims description 3
• 230000002401 inhibitory effect Effects 0.000 claims description 3
• 210000002569 neuron Anatomy 0.000 claims description 3
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• XFTQGGQXLLFMET-UHFFFAOYSA-N 3-[(5-methylpyrazin-2-yl)methyl]-2-sulfanylidene-7h-purin-6-one Chemical compound C1=NC(C)=CN=C1CN1C(=S)NC(=O)C2=C1N=CN2 XFTQGGQXLLFMET-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
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