RU2139284C1 - 4-гидроксипиран-2-оны, циклооктил-или бензопиран-2-оны, 4-гидрокси-2н-пиран-2-оны и 4-гидрокси-циклооктапиран-2-оны - Google Patents
4-гидроксипиран-2-оны, циклооктил-или бензопиран-2-оны, 4-гидрокси-2н-пиран-2-оны и 4-гидрокси-циклооктапиран-2-оны Download PDFInfo
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- RU2139284C1 RU2139284C1 RU96123286A RU96123286A RU2139284C1 RU 2139284 C1 RU2139284 C1 RU 2139284C1 RU 96123286 A RU96123286 A RU 96123286A RU 96123286 A RU96123286 A RU 96123286A RU 2139284 C1 RU2139284 C1 RU 2139284C1
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- RU
- Russia
- Prior art keywords
- phenyl
- hydroxy
- pyran
- oxo
- propyl
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- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical class C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 title claims description 39
- VNZOLPIHDIJPBZ-UHFFFAOYSA-N 4-hydroxypyran-2-one Chemical class OC=1C=COC(=O)C=1 VNZOLPIHDIJPBZ-UHFFFAOYSA-N 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 602
- -1 het Chemical group 0.000 claims abstract description 383
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 251
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 94
- 239000012634 fragment Substances 0.000 claims abstract description 38
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 240
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 125
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 117
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 100
- 229940124530 sulfonamide Drugs 0.000 claims description 52
- 125000000623 heterocyclic group Chemical group 0.000 claims description 45
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 31
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 30
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 27
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 20
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000001153 fluoro group Chemical group F* 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 17
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims description 16
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 11
- 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 11
- 229910052717 sulfur Chemical group 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
- 239000011593 sulfur Chemical group 0.000 claims description 9
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000002619 bicyclic group Chemical group 0.000 claims description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 239000004475 Arginine Substances 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Chemical group 0.000 claims description 7
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 7
- 125000006532 (C3-C5) alkyl group Chemical group 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
- 239000011591 potassium Substances 0.000 claims description 5
- 229910052700 potassium Inorganic materials 0.000 claims description 5
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 5
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 5
- RLEGNEMAZOQPDY-UHFFFAOYSA-N 3-cyclooctylpyran-2-one Chemical class O=C1OC=CC=C1C1CCCCCCC1 RLEGNEMAZOQPDY-UHFFFAOYSA-N 0.000 claims description 4
- DWBYVCQMWSZSHP-UHFFFAOYSA-N n-[3-[1-(4-hydroxy-6-oxo-2,2-dipropyl-3h-pyran-5-yl)propyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound O=C1OC(CCC)(CCC)CC(O)=C1C(CC)C1=CC=CC(NS(=O)(=O)C=2N=CN(C)C=2)=C1 DWBYVCQMWSZSHP-UHFFFAOYSA-N 0.000 claims description 4
- CPOJIWBHCUHYPR-UHFFFAOYSA-N n-[3-[1-(4-hydroxy-6-oxo-2,2-dipropyl-3h-pyran-5-yl)propyl]phenyl]quinoline-8-sulfonamide Chemical compound O=C1OC(CCC)(CCC)CC(O)=C1C(CC)C1=CC=CC(NS(=O)(=O)C=2C3=NC=CC=C3C=CC=2)=C1 CPOJIWBHCUHYPR-UHFFFAOYSA-N 0.000 claims description 4
- DDELSUNXQXSHNC-UHFFFAOYSA-N n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C1C(O)=C(C(C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)C(C)(C)C)C(=O)OC1(CCC)CCC1=CC=CC=C1 DDELSUNXQXSHNC-UHFFFAOYSA-N 0.000 claims description 4
- 125000004542 purin-6-yl group Chemical group N1=CN=C2N=CNC2=C1* 0.000 claims description 4
- 125000004260 quinazolin-2-yl group Chemical group [H]C1=NC(*)=NC2=C1C([H])=C([H])C([H])=C2[H] 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 4
- IDMNMIWJDJTSEZ-UHFFFAOYSA-N 3-phenylpyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=NC=CC=C1C1=CC=CC=C1 IDMNMIWJDJTSEZ-UHFFFAOYSA-N 0.000 claims description 3
- DKFOXCYPEGIHMT-UHFFFAOYSA-N 5-cyano-n-[3-[1-[4-hydroxy-6-oxo-2,2-bis(2-phenylethyl)-3h-pyran-5-yl]propyl]phenyl]pyridine-2-sulfonamide Chemical compound C=1C=CC(NS(=O)(=O)C=2N=CC(=CC=2)C#N)=CC=1C(CC)C(C(O1)=O)=C(O)CC1(CCC=1C=CC=CC=1)CCC1=CC=CC=C1 DKFOXCYPEGIHMT-UHFFFAOYSA-N 0.000 claims description 3
- WUOXAVXJDAZRNO-UHFFFAOYSA-N 5-cyano-n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]pyridine-2-sulfonamide Chemical compound C1C(O)=C(C(C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C#N)C=CC=2)C(C)(C)C)C(=O)OC1(CCC)CCC1=CC=CC=C1 WUOXAVXJDAZRNO-UHFFFAOYSA-N 0.000 claims description 3
- SLZNWUVSDZUVTO-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-(1,3-dicyclopropylpropan-2-yl)-4-hydroxy-2-oxopyran-3-yl]methyl]phenyl]-4-fluorobenzenesulfonamide Chemical compound OC=1C=C(C(CC2CC2)CC2CC2)OC(=O)C=1C(C=1C=C(NS(=O)(=O)C=2C=CC(F)=CC=2)C=CC=1)C1CC1 SLZNWUVSDZUVTO-UHFFFAOYSA-N 0.000 claims description 3
- HXDACLLDEJPDPL-UHFFFAOYSA-N 3-[[3-(1h-benzimidazol-2-ylsulfonylmethyl)phenyl]-cyclopropylmethyl]-4-hydroxychromen-2-one Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C(C=1C=C(CS(=O)(=O)C=2NC3=CC=CC=C3N=2)C=CC=1)C1CC1 HXDACLLDEJPDPL-UHFFFAOYSA-N 0.000 claims description 2
- AFAXKKURBHECKR-UHFFFAOYSA-N 3-[[3-(benzenesulfonylmethyl)phenyl]-cyclopropylmethyl]-4-hydroxy-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-2-one Chemical compound OC=1C=2CCCCCCC=2OC(=O)C=1C(C=1C=C(CS(=O)(=O)C=2C=CC=CC=2)C=CC=1)C1CC1 AFAXKKURBHECKR-UHFFFAOYSA-N 0.000 claims description 2
- FGYKZDNDRRRWFL-UHFFFAOYSA-N 3-[cyclopropyl-[3-(pyridin-2-ylsulfonylmethyl)phenyl]methyl]-4-hydroxy-6-(1-phenylbutan-2-yl)pyran-2-one Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(CS(=O)(=O)C=3N=CC=CC=3)C=CC=2)C(=O)OC=1C(CC)CC1=CC=CC=C1 FGYKZDNDRRRWFL-UHFFFAOYSA-N 0.000 claims description 2
- SHSUXUGDRARKMQ-UHFFFAOYSA-N 3-[cyclopropyl-[3-(pyridin-2-ylsulfonylmethyl)phenyl]methyl]-4-hydroxychromen-2-one Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C(C=1C=C(CS(=O)(=O)C=2N=CC=CC=2)C=CC=1)C1CC1 SHSUXUGDRARKMQ-UHFFFAOYSA-N 0.000 claims description 2
- JDLUWMUMZVJSCQ-UHFFFAOYSA-N 3-[cyclopropyl-[3-(pyrimidin-2-ylsulfonylmethyl)phenyl]methyl]-4-hydroxy-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-2-one Chemical compound OC=1C=2CCCCCCC=2OC(=O)C=1C(C=1C=C(CS(=O)(=O)C=2N=CC=CN=2)C=CC=1)C1CC1 JDLUWMUMZVJSCQ-UHFFFAOYSA-N 0.000 claims description 2
- AGRPABSPYRMWBR-UHFFFAOYSA-N 3-[cyclopropyl-[3-(quinolin-2-ylsulfonylmethyl)phenyl]methyl]-4-hydroxy-6-(1-phenylbutan-2-yl)pyran-2-one Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(CS(=O)(=O)C=3N=C4C=CC=CC4=CC=3)C=CC=2)C(=O)OC=1C(CC)CC1=CC=CC=C1 AGRPABSPYRMWBR-UHFFFAOYSA-N 0.000 claims description 2
- ODALELAXRCIMES-UHFFFAOYSA-N 3-[cyclopropyl-[3-(quinolin-2-ylsulfonylmethyl)phenyl]methyl]-4-hydroxychromen-2-one Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C(C=1C=C(CS(=O)(=O)C=2N=C3C=CC=CC3=CC=2)C=CC=1)C1CC1 ODALELAXRCIMES-UHFFFAOYSA-N 0.000 claims description 2
- FQZNMFPVTGULAX-UHFFFAOYSA-N 3-[cyclopropyl-[3-[(1-methylimidazol-4-yl)sulfonylmethyl]phenyl]methyl]-4-hydroxy-6-(1-phenylbutan-2-yl)pyran-2-one Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(CS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)C(=O)OC=1C(CC)CC1=CC=CC=C1 FQZNMFPVTGULAX-UHFFFAOYSA-N 0.000 claims description 2
- ZWJDTSHTRYXTLS-UHFFFAOYSA-N 3-[cyclopropyl-[3-[(1-methylimidazol-4-yl)sulfonylmethyl]phenyl]methyl]-4-hydroxychromen-2-one Chemical compound CN1C=NC(S(=O)(=O)CC=2C=C(C=CC=2)C(C2CC2)C=2C(OC3=CC=CC=C3C=2O)=O)=C1 ZWJDTSHTRYXTLS-UHFFFAOYSA-N 0.000 claims description 2
- ZYKCTQWAKJZELI-UHFFFAOYSA-N 4-[[3-[cyclopropyl-(4-hydroxy-2-oxochromen-3-yl)methyl]phenyl]methylsulfonyl]benzonitrile Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C(C=1C=C(CS(=O)(=O)C=2C=CC(=CC=2)C#N)C=CC=1)C1CC1 ZYKCTQWAKJZELI-UHFFFAOYSA-N 0.000 claims description 2
- PCJJJRSOLJBGTG-UHFFFAOYSA-N 4-[[3-[cyclopropyl-[4-hydroxy-2-oxo-6-(1-phenylbutan-2-yl)pyran-3-yl]methyl]phenyl]methylsulfonyl]benzonitrile Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(CS(=O)(=O)C=3C=CC(=CC=3)C#N)C=CC=2)C(=O)OC=1C(CC)CC1=CC=CC=C1 PCJJJRSOLJBGTG-UHFFFAOYSA-N 0.000 claims description 2
- RJXRWWHIZKLIFC-UHFFFAOYSA-N 4-cyano-N-[3-[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]propyl]phenyl]pyridine-2-sulfonamide Chemical compound C(#N)C1=CC(=NC=C1)S(=O)(=O)NC1=CC(=CC=C1)C(CC)C=1C(OC(CC=1O)(C1=CC=CC=C1)C1=CC=CC=C1)CC=O RJXRWWHIZKLIFC-UHFFFAOYSA-N 0.000 claims description 2
- YXOZDPNMDRQJOZ-UHFFFAOYSA-N 4-cyano-n-[3-[1-(4-hydroxy-6-oxo-2,2-dipropyl-3h-pyran-5-yl)propyl]phenyl]benzenesulfonamide Chemical compound O=C1OC(CCC)(CCC)CC(O)=C1C(CC)C1=CC=CC(NS(=O)(=O)C=2C=CC(=CC=2)C#N)=C1 YXOZDPNMDRQJOZ-UHFFFAOYSA-N 0.000 claims description 2
- KBNOQQLTUMJCJF-UHFFFAOYSA-N 4-cyano-n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]propyl]phenyl]pyridine-2-sulfonamide Chemical compound C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3N=CC=C(C=3)C#N)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 KBNOQQLTUMJCJF-UHFFFAOYSA-N 0.000 claims description 2
- JJUKGKSZZSLEBS-UHFFFAOYSA-N 4-fluoro-n-[3-[1-(4-hydroxy-6-oxo-2,2-dipropyl-3h-pyran-5-yl)propyl]phenyl]benzenesulfonamide Chemical compound O=C1OC(CCC)(CCC)CC(O)=C1C(CC)C1=CC=CC(NS(=O)(=O)C=2C=CC(F)=CC=2)=C1 JJUKGKSZZSLEBS-UHFFFAOYSA-N 0.000 claims description 2
- FAKDTHHSOVDTMS-UHFFFAOYSA-N 5-cyano-n-[3-[1-(4-hydroxy-6-oxo-2,2-dipropyl-3h-pyran-5-yl)-2,2-dimethylpropyl]phenyl]pyridine-2-sulfonamide Chemical compound O=C1OC(CCC)(CCC)CC(O)=C1C(C(C)(C)C)C1=CC=CC(NS(=O)(=O)C=2N=CC(=CC=2)C#N)=C1 FAKDTHHSOVDTMS-UHFFFAOYSA-N 0.000 claims description 2
- ZHDLFKICABABHZ-UHFFFAOYSA-N 5-cyano-n-[3-[1-(4-hydroxy-6-oxo-2,2-dipropyl-3h-pyran-5-yl)propyl]phenyl]pyridine-2-sulfonamide Chemical compound O=C1OC(CCC)(CCC)CC(O)=C1C(CC)C1=CC=CC(NS(=O)(=O)C=2N=CC(=CC=2)C#N)=C1 ZHDLFKICABABHZ-UHFFFAOYSA-N 0.000 claims description 2
- YIIKDYADFBAUNX-UHFFFAOYSA-N 5-cyano-n-[3-[1-[2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]pyridine-2-sulfonamide Chemical compound C1C(O)=C(C(C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C#N)C=CC=2)C(C)(C)C)C(=O)OC1(CCC)CCC1=CC=C(F)C=C1 YIIKDYADFBAUNX-UHFFFAOYSA-N 0.000 claims description 2
- FNGPDMVDSXJKKX-UHFFFAOYSA-N 5-cyano-n-[3-[1-[2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-2-propyl-3h-pyran-5-yl]propyl]phenyl]pyridine-2-sulfonamide Chemical compound C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C#N)C=CC=2)C(=O)OC1(CCC)CCC1=CC=C(F)C=C1 FNGPDMVDSXJKKX-UHFFFAOYSA-N 0.000 claims description 2
- HZNIOHBLXZBDEE-UHFFFAOYSA-N 5-cyano-n-[3-[1-[4-hydroxy-2,2-bis(2-methylpropyl)-6-oxo-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]pyridine-2-sulfonamide Chemical compound O=C1OC(CC(C)C)(CC(C)C)CC(O)=C1C(C(C)(C)C)C1=CC=CC(NS(=O)(=O)C=2N=CC(=CC=2)C#N)=C1 HZNIOHBLXZBDEE-UHFFFAOYSA-N 0.000 claims description 2
- WSBWKGLVMNROFG-UHFFFAOYSA-N 5-cyano-n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]propyl]phenyl]pyridine-2-sulfonamide Chemical compound C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C#N)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 WSBWKGLVMNROFG-UHFFFAOYSA-N 0.000 claims description 2
- GSTUBFJZGFVJHZ-UHFFFAOYSA-N 6-[[3-[cyclopropyl-(4-hydroxy-2-oxochromen-3-yl)methyl]phenyl]methylsulfonyl]pyridine-3-carbonitrile Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C(C=1C=C(CS(=O)(=O)C=2N=CC(=CC=2)C#N)C=CC=1)C1CC1 GSTUBFJZGFVJHZ-UHFFFAOYSA-N 0.000 claims description 2
- ZQVNSTTUJFMYGM-UHFFFAOYSA-N 6-[[3-[cyclopropyl-[4-hydroxy-2-oxo-6-(1-phenylbutan-2-yl)pyran-3-yl]methyl]phenyl]methylsulfonyl]pyridine-3-carbonitrile Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(CS(=O)(=O)C=3N=CC(=CC=3)C#N)C=CC=2)C(=O)OC=1C(CC)CC1=CC=CC=C1 ZQVNSTTUJFMYGM-UHFFFAOYSA-N 0.000 claims description 2
- GSLZBEXVWFVTIG-UHFFFAOYSA-N N-[3-[1-(2,4-dioxo-6,6-dipropyloxan-3-yl)propyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound CCCC1(CCC)CC(=O)C(C(CC)c2cccc(NS(=O)(=O)c3cn(C)cn3)c2)C(=O)O1 GSLZBEXVWFVTIG-UHFFFAOYSA-N 0.000 claims description 2
- BXHQUWTTYKXNQS-UHFFFAOYSA-N N-[3-[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]propyl]phenyl]-1,3-thiazole-4-sulfonamide Chemical compound OC1=C(C(OC(C1)(C1=CC=CC=C1)C1=CC=CC=C1)CC=O)C(CC)C=1C=C(C=CC=1)NS(=O)(=O)C=1N=CSC=1 BXHQUWTTYKXNQS-UHFFFAOYSA-N 0.000 claims description 2
- ULJQPPQPAVOMFF-UHFFFAOYSA-N N-[3-[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]propyl]phenyl]-1H-benzimidazole-2-sulfonamide Chemical compound OC1=C(C(OC(C1)(C1=CC=CC=C1)C1=CC=CC=C1)CC=O)C(CC)C=1C=C(C=CC=1)NS(=O)(=O)C1=NC2=C(N1)C=CC=C2 ULJQPPQPAVOMFF-UHFFFAOYSA-N 0.000 claims description 2
- LEAZNXXRBRXMGB-UHFFFAOYSA-N N-[3-[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]propyl]phenyl]-1H-imidazole-2-sulfonamide Chemical compound OC1=C(C(OC(C1)(C1=CC=CC=C1)C1=CC=CC=C1)CC=O)C(CC)C=1C=C(C=CC1)NS(=O)(=O)C=1NC=CN1 LEAZNXXRBRXMGB-UHFFFAOYSA-N 0.000 claims description 2
- DHBQGFCFUUENEL-UHFFFAOYSA-N N-[3-[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]propyl]phenyl]-7H-purine-6-sulfonamide Chemical compound OC1=C(C(OC(C1)(C1=CC=CC=C1)C1=CC=CC=C1)CC=O)C(CC)C=1C=C(C=CC=1)NS(=O)(=O)C1=C2NC=NC2=NC=N1 DHBQGFCFUUENEL-UHFFFAOYSA-N 0.000 claims description 2
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- QJCNFHOHDNDOMT-UHFFFAOYSA-N N-[3-[[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]cyclopropyl]methyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NC=2C=C(CC3(CC3)C=3C(OC(CC=3O)(C=3C=CC=CC=3)C=3C=CC=CC=3)CC=O)C=CC=2)=C1 QJCNFHOHDNDOMT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
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- NURFUQWJTPTBKU-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-(1,3-dicyclopropylpropan-2-yl)-4-hydroxy-2-oxopyran-3-yl]methyl]phenyl]-1h-imidazole-2-sulfonamide Chemical compound OC=1C=C(C(CC2CC2)CC2CC2)OC(=O)C=1C(C=1C=C(NS(=O)(=O)C=2NC=CN=2)C=CC=1)C1CC1 NURFUQWJTPTBKU-UHFFFAOYSA-N 0.000 claims description 2
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- WSBWKGLVMNROFG-SUYBVONHSA-N 5-cyano-n-[3-[(1s)-1-[(2r)-4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]propyl]phenyl]pyridine-2-sulfonamide Chemical compound C([C@@]1(CCC)OC(=O)C([C@@H](CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C#N)C=CC=2)=C(O)C1)CC1=CC=CC=C1 WSBWKGLVMNROFG-SUYBVONHSA-N 0.000 claims 2
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- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
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- LWRFDGCKGSOOLI-UHFFFAOYSA-N n-[3-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-3-yl)methyl]phenyl]quinazoline-2-sulfonamide Chemical compound OC=1C=2CCCCCCC=2OC(=O)C=1C(C=1C=C(NS(=O)(=O)C=2N=C3C=CC=CC3=CN=2)C=CC=1)C1CC1 LWRFDGCKGSOOLI-UHFFFAOYSA-N 0.000 claims 2
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- JCWFLYMBMGSWFG-UHFFFAOYSA-N 2-[[8-[3-[5-[cyclopropyl-[3-[(1-methylimidazol-2-yl)sulfonylamino]phenyl]methyl]-4-hydroxy-6-oxopyran-2-yl]propylamino]-8-oxooctanoyl]-methylamino]ethanesulfonic acid Chemical compound O=C1OC(CCCNC(=O)CCCCCCC(=O)N(CCS(O)(=O)=O)C)=CC(O)=C1C(C=1C=C(NS(=O)(=O)C=2N(C=CN=2)C)C=CC=1)C1CC1 JCWFLYMBMGSWFG-UHFFFAOYSA-N 0.000 claims 1
- UAMSGPPAABLQIS-UHFFFAOYSA-N 2-[[8-[3-[5-[cyclopropyl-[3-[(1-methylimidazol-4-yl)sulfonylamino]phenyl]methyl]-4-hydroxy-6-oxopyran-2-yl]pentylamino]-8-oxooctanoyl]-methylamino]ethanesulfonic acid Chemical compound O=C1OC(C(CCNC(=O)CCCCCCC(=O)N(C)CCS(O)(=O)=O)CC)=CC(O)=C1C(C=1C=C(NS(=O)(=O)C=2N=CN(C)C=2)C=CC=1)C1CC1 UAMSGPPAABLQIS-UHFFFAOYSA-N 0.000 claims 1
- AUVZIYNMEUNVEO-UHFFFAOYSA-N 2-[[8-[3-[5-[cyclopropyl-[3-[(1-methylimidazol-4-yl)sulfonylamino]phenyl]methyl]-4-hydroxy-6-oxopyran-2-yl]propylamino]-8-oxooctanoyl]-methylamino]ethanesulfonic acid Chemical compound O=C1OC(CCCNC(=O)CCCCCCC(=O)N(CCS(O)(=O)=O)C)=CC(O)=C1C(C=1C=C(NS(=O)(=O)C=2N=CN(C)C=2)C=CC=1)C1CC1 AUVZIYNMEUNVEO-UHFFFAOYSA-N 0.000 claims 1
- OSMUTHDWCQQEAB-UHFFFAOYSA-N 3-[[3-(1h-benzimidazol-2-ylsulfonylmethyl)phenyl]-cyclopropylmethyl]-4-hydroxy-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-2-one Chemical compound OC=1C=2CCCCCCC=2OC(=O)C=1C(C=1C=C(CS(=O)(=O)C=2NC3=CC=CC=C3N=2)C=CC=1)C1CC1 OSMUTHDWCQQEAB-UHFFFAOYSA-N 0.000 claims 1
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- JFZIIRCVFOAXCP-UHFFFAOYSA-N 6-[[3-[1-(4-hydroxy-6-oxo-2,2-dipropyl-3h-pyran-5-yl)propyl]phenyl]sulfamoyl]pyridine-3-carboxamide Chemical compound O=C1OC(CCC)(CCC)CC(O)=C1C(CC)C1=CC=CC(NS(=O)(=O)C=2N=CC(=CC=2)C(N)=O)=C1 JFZIIRCVFOAXCP-UHFFFAOYSA-N 0.000 claims 1
- PSISVOCFYRZRIG-UHFFFAOYSA-N 6-[[3-[1-[2,2-bis[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-3h-pyran-5-yl]propyl]phenyl]sulfamoyl]pyridine-3-carboxamide Chemical compound C=1C=CC(NS(=O)(=O)C=2N=CC(=CC=2)C(N)=O)=CC=1C(CC)C(C(O1)=O)=C(O)CC1(CCC=1C=CC(F)=CC=1)CCC1=CC=C(F)C=C1 PSISVOCFYRZRIG-UHFFFAOYSA-N 0.000 claims 1
- AAVAJZUFHHIPDJ-UHFFFAOYSA-N 6-[[3-[1-[2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-2-propyl-3h-pyran-5-yl]propyl]phenyl]sulfamoyl]pyridine-3-carboxamide Chemical compound C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(N)=O)C=CC=2)C(=O)OC1(CCC)CCC1=CC=C(F)C=C1 AAVAJZUFHHIPDJ-UHFFFAOYSA-N 0.000 claims 1
- KROSBOPLDYXUAB-UHFFFAOYSA-N 6-[[3-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-3-yl)methyl]phenyl]methylsulfonyl]pyridine-3-carbonitrile Chemical compound OC=1C=2CCCCCCC=2OC(=O)C=1C(C=1C=C(CS(=O)(=O)C=2N=CC(=CC=2)C#N)C=CC=1)C1CC1 KROSBOPLDYXUAB-UHFFFAOYSA-N 0.000 claims 1
- FACOZAPMHBSIEV-UHFFFAOYSA-N C1(CC1)C(C1=CC=C(C=C1)NS(=O)(=O)C1=NC=CC=C1)C1=C(C2=C(OC1=O)CCCCCC2)O Chemical compound C1(CC1)C(C1=CC=C(C=C1)NS(=O)(=O)C1=NC=CC=C1)C1=C(C2=C(OC1=O)CCCCCC2)O FACOZAPMHBSIEV-UHFFFAOYSA-N 0.000 claims 1
- BOPZEALUAHQHTO-UHFFFAOYSA-N N-[3-[1-(2,4-dioxo-6,6-dipentyloxan-3-yl)propyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound O=C1OC(CCCCC)(CCCCC)CC(=O)C1C(CC)C1=CC=CC(NS(=O)(=O)C=2N=CN(C)C=2)=C1 BOPZEALUAHQHTO-UHFFFAOYSA-N 0.000 claims 1
- GRXZZNAAYSZPRQ-UHFFFAOYSA-N N-[3-[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]propyl]phenyl]-N-methyl-1H-benzimidazole-2-sulfonamide Chemical compound OC1=C(C(OC(C1)(C1=CC=CC=C1)C1=CC=CC=C1)CC=O)C(CC)C=1C=C(C=CC=1)N(S(=O)(=O)C=1NC2=C(N=1)C=CC=C2)C GRXZZNAAYSZPRQ-UHFFFAOYSA-N 0.000 claims 1
- YGNVGVPIRLNPLM-UHFFFAOYSA-N N-[3-[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]propyl]phenyl]-N-methyl-1H-imidazole-2-sulfonamide Chemical compound OC1=C(C(OC(C1)(C1=CC=CC=C1)C1=CC=CC=C1)CC=O)C(CC)C=1C=C(C=CC=1)N(S(=O)(=O)C=1NC=CN=1)C YGNVGVPIRLNPLM-UHFFFAOYSA-N 0.000 claims 1
- GLWCLVAKNYSCKJ-UHFFFAOYSA-N N-[3-[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]propyl]phenyl]-N-methyl-7H-purine-6-sulfonamide Chemical compound OC1=C(C(OC(C1)(C1=CC=CC=C1)C1=CC=CC=C1)CC=O)C(CC)C=1C=C(C=CC=1)N(S(=O)(=O)C1=C2NC=NC2=NC=N1)C GLWCLVAKNYSCKJ-UHFFFAOYSA-N 0.000 claims 1
- CVANVZOPUPHPCB-UHFFFAOYSA-N N-[3-[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]propyl]phenyl]-N-methylpyridine-2-sulfonamide Chemical compound OC1=C(C(OC(C1)(C1=CC=CC=C1)C1=CC=CC=C1)CC=O)C(CC)C=1C=C(C=CC=1)N(S(=O)(=O)C1=NC=CC=C1)C CVANVZOPUPHPCB-UHFFFAOYSA-N 0.000 claims 1
- WEGZWFIRTVZLGG-UHFFFAOYSA-N N-[3-[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]propyl]phenyl]-N-methylpyrimidine-2-sulfonamide Chemical compound OC1=C(C(OC(C1)(C1=CC=CC=C1)C1=CC=CC=C1)CC=O)C(CC)C=1C=C(C=CC=1)N(S(=O)(=O)C1=NC=CC=N1)C WEGZWFIRTVZLGG-UHFFFAOYSA-N 0.000 claims 1
- VYYZZUKATOZNAS-UHFFFAOYSA-N N-[3-[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]propyl]phenyl]-N-methylquinazoline-2-sulfonamide Chemical compound OC1=C(C(OC(C1)(C1=CC=CC=C1)C1=CC=CC=C1)CC=O)C(CC)C=1C=C(C=CC=1)N(S(=O)(=O)C1=NC2=CC=CC=C2C=N1)C VYYZZUKATOZNAS-UHFFFAOYSA-N 0.000 claims 1
- RMOMEJJJBDPWES-UHFFFAOYSA-N N-[3-[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]propyl]phenyl]-N-methylquinoline-2-sulfonamide Chemical compound OC1=C(C(OC(C1)(C1=CC=CC=C1)C1=CC=CC=C1)CC=O)C(CC)C=1C=C(C=CC=1)N(S(=O)(=O)C1=NC2=CC=CC=C2C=C1)C RMOMEJJJBDPWES-UHFFFAOYSA-N 0.000 claims 1
- VTKSDODUQKRPGD-UHFFFAOYSA-N N-[3-[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]propyl]phenyl]quinazoline-2-sulfonamide Chemical compound OC1=C(C(OC(C1)(C1=CC=CC=C1)C1=CC=CC=C1)CC=O)C(CC)C=1C=C(C=CC=1)NS(=O)(=O)C1=NC2=CC=CC=C2C=N1 VTKSDODUQKRPGD-UHFFFAOYSA-N 0.000 claims 1
- FMTMTBPFLDQKED-UHFFFAOYSA-N N-[3-[5-[[3-(1H-benzimidazol-2-ylsulfonylamino)phenyl]-cyclopropylmethyl]-4-hydroxy-6-oxopyran-2-yl]propyl]piperazine-1-carboxamide Chemical compound O1C(=O)C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3NC4=CC=CC=C4N=3)C=CC=2)=C(O)C=C1CCCNC(=O)N1CCNCC1 FMTMTBPFLDQKED-UHFFFAOYSA-N 0.000 claims 1
- OIRPFQNTAVOHIB-UHFFFAOYSA-N N-[3-[5-[[3-(benzenesulfonamido)phenyl]-cyclopropylmethyl]-4-hydroxy-6-oxopyran-2-yl]propyl]piperazine-1-carboxamide Chemical compound O1C(=O)C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3C=CC=CC=3)C=CC=2)=C(O)C=C1CCCNC(=O)N1CCNCC1 OIRPFQNTAVOHIB-UHFFFAOYSA-N 0.000 claims 1
- YRLZNQLZGGKOHN-UHFFFAOYSA-N N-[3-[5-[cyclopropyl-[3-(1H-imidazol-2-ylsulfonylamino)phenyl]methyl]-4-hydroxy-6-oxopyran-2-yl]propyl]piperazine-1-carboxamide Chemical compound O1C(=O)C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3NC=CN=3)C=CC=2)=C(O)C=C1CCCNC(=O)N1CCNCC1 YRLZNQLZGGKOHN-UHFFFAOYSA-N 0.000 claims 1
- WOULXJMFMKDTOH-UHFFFAOYSA-N N-[3-[5-[cyclopropyl-[3-(pyridin-2-ylsulfonylamino)phenyl]methyl]-4-hydroxy-6-oxopyran-2-yl]propyl]piperazine-1-carboxamide Chemical compound O1C(=O)C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3N=CC=CC=3)C=CC=2)=C(O)C=C1CCCNC(=O)N1CCNCC1 WOULXJMFMKDTOH-UHFFFAOYSA-N 0.000 claims 1
- QJBGMDNEESZGTF-UHFFFAOYSA-N N-[4-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-3-yl)methyl]phenyl]-4-methylpyrimidine-2-sulfonamide Chemical compound C1(CC1)C(C1=CC=C(C=C1)NS(=O)(=O)C1=NC=CC(=N1)C)C1=C(C2=C(OC1=O)CCCCCC2)O QJBGMDNEESZGTF-UHFFFAOYSA-N 0.000 claims 1
- AJMAITKWFVYVBM-UHFFFAOYSA-N N-[4-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-3-yl)methyl]phenyl]pyrazine-2-sulfonamide Chemical compound C1(CC1)C(C1=CC=C(C=C1)NS(=O)(=O)C1=NC=CN=C1)C1=C(C2=C(OC1=O)CCCCCC2)O AJMAITKWFVYVBM-UHFFFAOYSA-N 0.000 claims 1
- UGOTVDDXTSWPGE-UHFFFAOYSA-N N-[4-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-3-yl)methyl]phenyl]pyridine-4-sulfonamide Chemical compound C1(CC1)C(C1=CC=C(C=C1)NS(=O)(=O)C1=CC=NC=C1)C1=C(C2=C(OC1=O)CCCCCC2)O UGOTVDDXTSWPGE-UHFFFAOYSA-N 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- XFMOIOCPWIEJHC-UHFFFAOYSA-N ethyl 2-[[3-[cyclopropyl-(4-hydroxy-2-oxochromen-3-yl)methyl]phenyl]sulfamoyl]-1H-imidazole-5-carboxylate Chemical compound N1C(C(=O)OCC)=CN=C1S(=O)(=O)NC1=CC=CC(C(C2CC2)C=2C(OC3=CC=CC=C3C=2O)=O)=C1 XFMOIOCPWIEJHC-UHFFFAOYSA-N 0.000 claims 1
- CXJABNUZLUSTNI-UHFFFAOYSA-N ethyl 2-[[3-[cyclopropyl-[4-hydroxy-6-[1-(oxan-4-yl)butan-2-yl]-2-oxopyran-3-yl]methyl]phenyl]sulfamoyl]-1H-imidazole-5-carboxylate Chemical compound N1C(C(=O)OCC)=CN=C1S(=O)(=O)NC1=CC=CC(C(C2CC2)C=2C(OC(=CC=2O)C(CC)CC2CCOCC2)=O)=C1 CXJABNUZLUSTNI-UHFFFAOYSA-N 0.000 claims 1
- VGVVCRSKLMJGMX-UHFFFAOYSA-N ethyl 2-[[3-[cyclopropyl-[6-[2-(1-ethylcyclohexa-2,4-dien-1-yl)ethyl]-4-hydroxy-2-oxopyran-3-yl]methyl]phenyl]sulfamoyl]-1H-imidazole-5-carboxylate Chemical compound N1C(C(=O)OCC)=CN=C1S(=O)(=O)NC1=CC=CC(C(C2CC2)C=2C(OC(CCC3(CC)C=CC=CC3)=CC=2O)=O)=C1 VGVVCRSKLMJGMX-UHFFFAOYSA-N 0.000 claims 1
- SBINOEYHZPHFRC-UHFFFAOYSA-N n-[2-[4-hydroxy-5-[1-[3-[(1-methylimidazol-4-yl)sulfonylamino]phenyl]propyl]-6-oxo-2-propyl-3h-pyran-2-yl]ethyl]-1-methylimidazole-4-sulfonamide Chemical compound C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)C(=O)OC1(CCC)CCNS(=O)(=O)C1=CN(C)C=N1 SBINOEYHZPHFRC-UHFFFAOYSA-N 0.000 claims 1
- LYUJJKJZIZRGMA-GRKNLSHJSA-N n-[3-[(1r)-1-[(2r)-2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C([C@@]1(CCC)OC(=O)C([C@@H](C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)C(C)(C)C)=C(O)C1)CC1=CC=C(F)C=C1 LYUJJKJZIZRGMA-GRKNLSHJSA-N 0.000 claims 1
- XIZNTPWHVJBYBH-FUFSCUOVSA-N n-[3-[(1r)-1-[(2r)-2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-2-propyl-3h-pyran-5-yl]propyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C([C@@]1(CCC)OC(=O)C([C@H](CC)C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)=C(O)C1)CC1=CC=C(F)C=C1 XIZNTPWHVJBYBH-FUFSCUOVSA-N 0.000 claims 1
- DDELSUNXQXSHNC-GRKNLSHJSA-N n-[3-[(1r)-1-[(2r)-4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C([C@@]1(CCC)OC(=O)C([C@@H](C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)C(C)(C)C)=C(O)C1)CC1=CC=CC=C1 DDELSUNXQXSHNC-GRKNLSHJSA-N 0.000 claims 1
- LRGGJJZCDSKECU-FUFSCUOVSA-N n-[3-[(1r)-1-[(2r)-4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]propyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C([C@@]1(CCC)OC(=O)C([C@H](CC)C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)=C(O)C1)CC1=CC=CC=C1 LRGGJJZCDSKECU-FUFSCUOVSA-N 0.000 claims 1
- LYUJJKJZIZRGMA-MVSFAKPFSA-N n-[3-[(1r)-1-[(2s)-2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C([C@]1(CCC)OC(=O)C([C@@H](C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)C(C)(C)C)=C(O)C1)CC1=CC=C(F)C=C1 LYUJJKJZIZRGMA-MVSFAKPFSA-N 0.000 claims 1
- XIZNTPWHVJBYBH-GIGWZHCTSA-N n-[3-[(1r)-1-[(2s)-2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-2-propyl-3h-pyran-5-yl]propyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C([C@]1(CCC)OC(=O)C([C@H](CC)C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)=C(O)C1)CC1=CC=C(F)C=C1 XIZNTPWHVJBYBH-GIGWZHCTSA-N 0.000 claims 1
- DDELSUNXQXSHNC-MVSFAKPFSA-N n-[3-[(1r)-1-[(2s)-4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C([C@]1(CCC)OC(=O)C([C@@H](C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)C(C)(C)C)=C(O)C1)CC1=CC=CC=C1 DDELSUNXQXSHNC-MVSFAKPFSA-N 0.000 claims 1
- LRGGJJZCDSKECU-GIGWZHCTSA-N n-[3-[(1r)-1-[(2s)-4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]propyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C([C@]1(CCC)OC(=O)C([C@H](CC)C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)=C(O)C1)CC1=CC=CC=C1 LRGGJJZCDSKECU-GIGWZHCTSA-N 0.000 claims 1
- ZUUVMQIINQIUJN-MGBGTMOVSA-N n-[3-[(1r)-1-[4-hydroxy-6-oxo-2,2-bis(2-phenylethyl)-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NC=2C=C(C=CC=2)[C@H](C=2C(OC(CCC=3C=CC=CC=3)(CCC=3C=CC=CC=3)CC=2O)=O)C(C)(C)C)=C1 ZUUVMQIINQIUJN-MGBGTMOVSA-N 0.000 claims 1
- LYUJJKJZIZRGMA-QCENPCRXSA-N n-[3-[(1s)-1-[(2r)-2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C([C@@]1(CCC)OC(=O)C([C@H](C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)C(C)(C)C)=C(O)C1)CC1=CC=C(F)C=C1 LYUJJKJZIZRGMA-QCENPCRXSA-N 0.000 claims 1
- XIZNTPWHVJBYBH-PWUYWRBVSA-N n-[3-[(1s)-1-[(2r)-2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-2-propyl-3h-pyran-5-yl]propyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C([C@@]1(CCC)OC(=O)C([C@@H](CC)C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)=C(O)C1)CC1=CC=C(F)C=C1 XIZNTPWHVJBYBH-PWUYWRBVSA-N 0.000 claims 1
- DDELSUNXQXSHNC-QCENPCRXSA-N n-[3-[(1s)-1-[(2r)-4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C([C@@]1(CCC)OC(=O)C([C@H](C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)C(C)(C)C)=C(O)C1)CC1=CC=CC=C1 DDELSUNXQXSHNC-QCENPCRXSA-N 0.000 claims 1
- LRGGJJZCDSKECU-PWUYWRBVSA-N n-[3-[(1s)-1-[(2r)-4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]propyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C([C@@]1(CCC)OC(=O)C([C@@H](CC)C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)=C(O)C1)CC1=CC=CC=C1 LRGGJJZCDSKECU-PWUYWRBVSA-N 0.000 claims 1
- XIZNTPWHVJBYBH-OUTSHDOLSA-N n-[3-[(1s)-1-[(2s)-2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-2-propyl-3h-pyran-5-yl]propyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C([C@]1(CCC)OC(=O)C([C@@H](CC)C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)=C(O)C1)CC1=CC=C(F)C=C1 XIZNTPWHVJBYBH-OUTSHDOLSA-N 0.000 claims 1
- DDELSUNXQXSHNC-IZEXYCQBSA-N n-[3-[(1s)-1-[(2s)-4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C([C@]1(CCC)OC(=O)C([C@H](C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)C(C)(C)C)=C(O)C1)CC1=CC=CC=C1 DDELSUNXQXSHNC-IZEXYCQBSA-N 0.000 claims 1
- LRGGJJZCDSKECU-OUTSHDOLSA-N n-[3-[(1s)-1-[(2s)-4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]propyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C([C@]1(CCC)OC(=O)C([C@@H](CC)C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)=C(O)C1)CC1=CC=CC=C1 LRGGJJZCDSKECU-OUTSHDOLSA-N 0.000 claims 1
- ZUUVMQIINQIUJN-XIFFEERXSA-N n-[3-[(1s)-1-[4-hydroxy-6-oxo-2,2-bis(2-phenylethyl)-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NC=2C=C(C=CC=2)[C@@H](C=2C(OC(CCC=3C=CC=CC=3)(CCC=3C=CC=CC=3)CC=2O)=O)C(C)(C)C)=C1 ZUUVMQIINQIUJN-XIFFEERXSA-N 0.000 claims 1
- SUJUHGSWHZTSEU-SUHMBNCMSA-N n-[3-[(1s)-1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]propyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide Chemical compound C1C(O)=C([C@@H](CC)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 SUJUHGSWHZTSEU-SUHMBNCMSA-N 0.000 claims 1
- SELVWOUUEBTPLK-UHFFFAOYSA-N n-[3-[1-(4-hydroxy-6-oxo-2,2-dipropyl-3h-pyran-5-yl)-2,2-dimethylpropyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound O=C1OC(CCC)(CCC)CC(O)=C1C(C(C)(C)C)C1=CC=CC(NS(=O)(=O)C=2N=CN(C)C=2)=C1 SELVWOUUEBTPLK-UHFFFAOYSA-N 0.000 claims 1
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- XIZNTPWHVJBYBH-UHFFFAOYSA-N n-[3-[1-[2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-2-propyl-3h-pyran-5-yl]propyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)C(=O)OC1(CCC)CCC1=CC=C(F)C=C1 XIZNTPWHVJBYBH-UHFFFAOYSA-N 0.000 claims 1
- OADRMKHZZGGHSL-UHFFFAOYSA-N n-[3-[1-[4-hydroxy-2,2-bis(2-methylpropyl)-6-oxo-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound O=C1OC(CC(C)C)(CC(C)C)CC(O)=C1C(C(C)(C)C)C1=CC=CC(NS(=O)(=O)C=2N=CN(C)C=2)=C1 OADRMKHZZGGHSL-UHFFFAOYSA-N 0.000 claims 1
- DPZHGXSOHOQGTQ-UHFFFAOYSA-N n-[3-[1-[4-hydroxy-6-oxo-2,2-bis(2-phenylethyl)-3h-pyran-5-yl]propyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C=1C=CC(NS(=O)(=O)C=2N=CN(C)C=2)=CC=1C(CC)C(C(O1)=O)=C(O)CC1(CCC=1C=CC=CC=1)CCC1=CC=CC=C1 DPZHGXSOHOQGTQ-UHFFFAOYSA-N 0.000 claims 1
- GBDZPSACWUYCKN-UHFFFAOYSA-N n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]propyl]phenyl]quinoline-8-sulfonamide Chemical compound C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3C4=NC=CC=C4C=CC=3)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 GBDZPSACWUYCKN-UHFFFAOYSA-N 0.000 claims 1
- DRAYFDICDXSBQF-UHFFFAOYSA-N n-[3-[5-[cyclopropyl-[3-[(1-methylimidazol-4-yl)sulfonylamino]phenyl]methyl]-4-hydroxy-6-oxopyran-2-yl]pentyl]-1-methylimidazole-4-sulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)C(=O)OC=1C(CC)CCNS(=O)(=O)C1=CN(C)C=N1 DRAYFDICDXSBQF-UHFFFAOYSA-N 0.000 claims 1
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- SEDLBYUCIWQTFN-UHFFFAOYSA-N n-[3-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-3-yl)methyl]phenyl]-4-fluoro-n-methylbenzenesulfonamide Chemical compound C=1C=C(F)C=CC=1S(=O)(=O)N(C)C(C=1)=CC=CC=1C(C=1C(OC=2CCCCCCC=2C=1O)=O)C1CC1 SEDLBYUCIWQTFN-UHFFFAOYSA-N 0.000 claims 1
- YLVDUXWURRFRCG-UHFFFAOYSA-N n-[3-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-3-yl)methyl]phenyl]-7h-purine-6-sulfonamide Chemical compound OC=1C=2CCCCCCC=2OC(=O)C=1C(C=1C=C(NS(=O)(=O)C=2C=3NC=NC=3N=CN=2)C=CC=1)C1CC1 YLVDUXWURRFRCG-UHFFFAOYSA-N 0.000 claims 1
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- FINVAQCUIIGUBQ-UHFFFAOYSA-N n-[3-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-3-yl)methyl]phenyl]-n-methyl-1h-imidazole-2-sulfonamide Chemical compound N=1C=CNC=1S(=O)(=O)N(C)C(C=1)=CC=CC=1C(C=1C(OC=2CCCCCCC=2C=1O)=O)C1CC1 FINVAQCUIIGUBQ-UHFFFAOYSA-N 0.000 claims 1
- UZDAMSOTCGSWCC-UHFFFAOYSA-N n-[3-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-3-yl)methyl]phenyl]-n-methyl-7h-purine-6-sulfonamide Chemical compound N=1C=NC=2N=CNC=2C=1S(=O)(=O)N(C)C(C=1)=CC=CC=1C(C=1C(OC=2CCCCCCC=2C=1O)=O)C1CC1 UZDAMSOTCGSWCC-UHFFFAOYSA-N 0.000 claims 1
- VCWFMNOXZBVLSH-UHFFFAOYSA-N n-[3-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-3-yl)methyl]phenyl]-n-methylpyridine-2-sulfonamide Chemical compound C=1C=CC=NC=1S(=O)(=O)N(C)C(C=1)=CC=CC=1C(C=1C(OC=2CCCCCCC=2C=1O)=O)C1CC1 VCWFMNOXZBVLSH-UHFFFAOYSA-N 0.000 claims 1
- GCXSOIODDJUSGI-UHFFFAOYSA-N n-[3-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-3-yl)methyl]phenyl]-n-methylpyrimidine-2-sulfonamide Chemical compound N=1C=CC=NC=1S(=O)(=O)N(C)C(C=1)=CC=CC=1C(C=1C(OC=2CCCCCCC=2C=1O)=O)C1CC1 GCXSOIODDJUSGI-UHFFFAOYSA-N 0.000 claims 1
- RQKCSFUJQXUJFJ-UHFFFAOYSA-N n-[3-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-3-yl)methyl]phenyl]pyrimidine-2-sulfonamide Chemical compound OC=1C=2CCCCCCC=2OC(=O)C=1C(C=1C=C(NS(=O)(=O)C=2N=CC=CN=2)C=CC=1)C1CC1 RQKCSFUJQXUJFJ-UHFFFAOYSA-N 0.000 claims 1
- IWFYGSGCRXKOFT-UHFFFAOYSA-N n-[3-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-3-yl)methyl]phenyl]quinoline-2-sulfonamide Chemical compound OC=1C=2CCCCCCC=2OC(=O)C=1C(C=1C=C(NS(=O)(=O)C=2N=C3C=CC=CC3=CC=2)C=CC=1)C1CC1 IWFYGSGCRXKOFT-UHFFFAOYSA-N 0.000 claims 1
- RAUZSEFLHWFIPS-UHFFFAOYSA-N n-[3-[cyclopropyl-(4-hydroxy-2-oxochromen-3-yl)methyl]phenyl]-1,3-thiazole-4-sulfonamide Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C(C=1C=C(NS(=O)(=O)C=2N=CSC=2)C=CC=1)C1CC1 RAUZSEFLHWFIPS-UHFFFAOYSA-N 0.000 claims 1
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- AKAMOGIHKMRDBI-UHFFFAOYSA-N n-[3-[cyclopropyl-(4-hydroxy-2-oxochromen-3-yl)methyl]phenyl]pyrazole-1-sulfonamide Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C(C=1C=C(NS(=O)(=O)N2N=CC=C2)C=CC=1)C1CC1 AKAMOGIHKMRDBI-UHFFFAOYSA-N 0.000 claims 1
- MJQYPZICNAFSSZ-UHFFFAOYSA-N n-[3-[cyclopropyl-(4-hydroxy-2-oxochromen-3-yl)methyl]phenyl]pyridine-2-sulfonamide Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C(C=1C=C(NS(=O)(=O)C=2N=CC=CC=2)C=CC=1)C1CC1 MJQYPZICNAFSSZ-UHFFFAOYSA-N 0.000 claims 1
- QETLHXTVGDTKGA-UHFFFAOYSA-N n-[3-[cyclopropyl-(4-hydroxy-2-oxochromen-3-yl)methyl]phenyl]quinazoline-2-sulfonamide Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C(C=1C=C(NS(=O)(=O)C=2N=C3C=CC=CC3=CN=2)C=CC=1)C1CC1 QETLHXTVGDTKGA-UHFFFAOYSA-N 0.000 claims 1
- VIYHEHLXUREGIV-UHFFFAOYSA-N n-[3-[cyclopropyl-(4-hydroxy-2-oxochromen-3-yl)methyl]phenyl]quinoline-2-sulfonamide Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C(C=1C=C(NS(=O)(=O)C=2N=C3C=CC=CC3=CC=2)C=CC=1)C1CC1 VIYHEHLXUREGIV-UHFFFAOYSA-N 0.000 claims 1
- FVCKWPQMLLACPQ-UHFFFAOYSA-N n-[3-[cyclopropyl-(4-hydroxy-7-methoxy-2-oxochromen-3-yl)methyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound O=C1OC2=CC(OC)=CC=C2C(O)=C1C(C=1C=C(NS(=O)(=O)C=2N=CN(C)C=2)C=CC=1)C1CC1 FVCKWPQMLLACPQ-UHFFFAOYSA-N 0.000 claims 1
- SHSTWKPBCINYTO-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-6-[1-(oxan-4-yl)butan-2-yl]-2-oxopyran-3-yl]methyl]phenyl]-1,3-thiazole-4-sulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3N=CSC=3)C=CC=2)C(=O)OC=1C(CC)CC1CCOCC1 SHSTWKPBCINYTO-UHFFFAOYSA-N 0.000 claims 1
- QBRNMLIKYLIHGA-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-6-[1-(oxan-4-yl)butan-2-yl]-2-oxopyran-3-yl]methyl]phenyl]-1-methylimidazole-2-sulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3N(C=CN=3)C)C=CC=2)C(=O)OC=1C(CC)CC1CCOCC1 QBRNMLIKYLIHGA-UHFFFAOYSA-N 0.000 claims 1
- FJLRWSQCOWCGTM-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-6-[1-(oxan-4-yl)butan-2-yl]-2-oxopyran-3-yl]methyl]phenyl]-1h-benzimidazole-2-sulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3NC4=CC=CC=C4N=3)C=CC=2)C(=O)OC=1C(CC)CC1CCOCC1 FJLRWSQCOWCGTM-UHFFFAOYSA-N 0.000 claims 1
- ZPWVTQPMBHVDJN-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-6-[1-(oxan-4-yl)butan-2-yl]-2-oxopyran-3-yl]methyl]phenyl]-2-hydroxybenzenesulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3C(=CC=CC=3)O)C=CC=2)C(=O)OC=1C(CC)CC1CCOCC1 ZPWVTQPMBHVDJN-UHFFFAOYSA-N 0.000 claims 1
- RVBVCFTYXVPMLN-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-6-[1-(oxan-4-yl)butan-2-yl]-2-oxopyran-3-yl]methyl]phenyl]-3-hydroxypyridine-2-sulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3C(=CC=CN=3)O)C=CC=2)C(=O)OC=1C(CC)CC1CCOCC1 RVBVCFTYXVPMLN-UHFFFAOYSA-N 0.000 claims 1
- RFMMODSAWBLCGC-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-6-[1-(oxan-4-yl)butan-2-yl]-2-oxopyran-3-yl]methyl]phenyl]-7h-purine-6-sulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3C=4NC=NC=4N=CN=3)C=CC=2)C(=O)OC=1C(CC)CC1CCOCC1 RFMMODSAWBLCGC-UHFFFAOYSA-N 0.000 claims 1
- GLACTYYNKNWMBE-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-6-[1-(oxan-4-yl)butan-2-yl]-2-oxopyran-3-yl]methyl]phenyl]pyrazole-1-sulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)N3N=CC=C3)C=CC=2)C(=O)OC=1C(CC)CC1CCOCC1 GLACTYYNKNWMBE-UHFFFAOYSA-N 0.000 claims 1
- GANDDCSDAYBRKY-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-6-[1-(oxan-4-yl)butan-2-yl]-2-oxopyran-3-yl]methyl]phenyl]pyridine-2-sulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3N=CC=CC=3)C=CC=2)C(=O)OC=1C(CC)CC1CCOCC1 GANDDCSDAYBRKY-UHFFFAOYSA-N 0.000 claims 1
- GZWFVIQOKHNKJM-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-6-[1-(oxan-4-yl)butan-2-yl]-2-oxopyran-3-yl]methyl]phenyl]quinazoline-2-sulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3N=C4C=CC=CC4=CN=3)C=CC=2)C(=O)OC=1C(CC)CC1CCOCC1 GZWFVIQOKHNKJM-UHFFFAOYSA-N 0.000 claims 1
- JRKAHMJFFAFMHP-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-6-[1-(oxan-4-yl)butan-2-yl]-2-oxopyran-3-yl]methyl]phenyl]quinoline-2-sulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3N=C4C=CC=CC4=CC=3)C=CC=2)C(=O)OC=1C(CC)CC1CCOCC1 JRKAHMJFFAFMHP-UHFFFAOYSA-N 0.000 claims 1
- WMHCXVBLTNOAJN-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]methyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 WMHCXVBLTNOAJN-UHFFFAOYSA-N 0.000 claims 1
- XMXFPJACKXUQAF-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-7-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]-2-oxochromen-3-yl]methyl]phenyl]pyridine-2-sulfonamide Chemical compound O=C1OC2=CC(OCCOCCOCCOC)=CC=C2C(O)=C1C(C=1C=C(NS(=O)(=O)C=2N=CC=CC=2)C=CC=1)C1CC1 XMXFPJACKXUQAF-UHFFFAOYSA-N 0.000 claims 1
- YKGGUIOYLXDVSM-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-7-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]-2-oxochromen-3-yl]methyl]phenyl]quinoline-8-sulfonamide Chemical compound O=C1OC2=CC(OCCOCCOCCOC)=CC=C2C(O)=C1C(C=1C=C(NS(=O)(=O)C=2C3=NC=CC=C3C=CC=2)C=CC=1)C1CC1 YKGGUIOYLXDVSM-UHFFFAOYSA-N 0.000 claims 1
- XDASXYHIYMOGQE-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-(1,3-dicyclopropylpropan-2-yl)-4-hydroxy-2-oxopyran-3-yl]methyl]phenyl]-1-methylimidazole-2-sulfonamide Chemical compound CN1C=CN=C1S(=O)(=O)NC1=CC=CC(C(C2CC2)C=2C(OC(=CC=2O)C(CC2CC2)CC2CC2)=O)=C1 XDASXYHIYMOGQE-UHFFFAOYSA-N 0.000 claims 1
- YTVNVRKKXQDZQA-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-[2-(1-ethylcyclohexa-2,4-dien-1-yl)ethyl]-4-hydroxy-2-oxopyran-3-yl]methyl]phenyl]-1,3-thiazole-4-sulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3N=CSC=3)C=CC=2)C(=O)OC=1CCC1(CC)CC=CC=C1 YTVNVRKKXQDZQA-UHFFFAOYSA-N 0.000 claims 1
- OHIFAZIPWXYIII-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-[2-(1-ethylcyclohexa-2,4-dien-1-yl)ethyl]-4-hydroxy-2-oxopyran-3-yl]methyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)C(=O)OC=1CCC1(CC)CC=CC=C1 OHIFAZIPWXYIII-UHFFFAOYSA-N 0.000 claims 1
- CRMKJUODSUYEGY-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-[2-(1-ethylcyclohexa-2,4-dien-1-yl)ethyl]-4-hydroxy-2-oxopyran-3-yl]methyl]phenyl]-1h-benzimidazole-2-sulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3NC4=CC=CC=C4N=3)C=CC=2)C(=O)OC=1CCC1(CC)CC=CC=C1 CRMKJUODSUYEGY-UHFFFAOYSA-N 0.000 claims 1
- JVPJFIJBUHEIOH-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-[2-(1-ethylcyclohexa-2,4-dien-1-yl)ethyl]-4-hydroxy-2-oxopyran-3-yl]methyl]phenyl]-1h-imidazole-2-sulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3NC=CN=3)C=CC=2)C(=O)OC=1CCC1(CC)CC=CC=C1 JVPJFIJBUHEIOH-UHFFFAOYSA-N 0.000 claims 1
- RYEFEFHGXSPZGE-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-[2-(1-ethylcyclohexa-2,4-dien-1-yl)ethyl]-4-hydroxy-2-oxopyran-3-yl]methyl]phenyl]-2-hydroxybenzenesulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3C(=CC=CC=3)O)C=CC=2)C(=O)OC=1CCC1(CC)CC=CC=C1 RYEFEFHGXSPZGE-UHFFFAOYSA-N 0.000 claims 1
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Images
Classifications
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- 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
- C07D405/12—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 chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
-
- 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
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- 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
- A61P31/14—Antivirals for RNA viruses
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- 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
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/74—Benzo[b]pyrans, hydrogenated in the carbocyclic ring
-
- 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
- C07D405/14—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 three or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Molecular Biology (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23881794A | 1994-05-06 | 1994-05-06 | |
| US08/238,817 | 1994-05-06 | ||
| US34936194A | 1994-12-02 | 1994-12-02 | |
| US08/349,361 | 1994-12-02 | ||
| PCT/US1995/005219 WO1995030670A2 (en) | 1994-05-06 | 1995-05-04 | Pyranone compounds useful to treat retroviral infections |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU96123286A RU96123286A (ru) | 1999-01-20 |
| RU2139284C1 true RU2139284C1 (ru) | 1999-10-10 |
Family
ID=26931995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU96123286A RU2139284C1 (ru) | 1994-05-06 | 1995-05-04 | 4-гидроксипиран-2-оны, циклооктил-или бензопиран-2-оны, 4-гидрокси-2н-пиран-2-оны и 4-гидрокси-циклооктапиран-2-оны |
Country Status (32)
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| EP (1) | EP0758327B1 (OSRAM) |
| JP (1) | JP3883206B2 (OSRAM) |
| KR (1) | KR100445929B1 (OSRAM) |
| CN (2) | CN1154642C (OSRAM) |
| AT (1) | ATE236894T1 (OSRAM) |
| AU (2) | AU701965B2 (OSRAM) |
| BR (1) | BR9507615A (OSRAM) |
| CA (2) | CA2187523C (OSRAM) |
| CO (1) | CO4810313A1 (OSRAM) |
| CZ (1) | CZ296515B6 (OSRAM) |
| DE (2) | DE122006000014I2 (OSRAM) |
| DK (1) | DK0758327T3 (OSRAM) |
| ES (1) | ES2192201T3 (OSRAM) |
| FI (1) | FI117387B (OSRAM) |
| FR (1) | FR05C0047I2 (OSRAM) |
| HU (1) | HU228057B1 (OSRAM) |
| IL (3) | IL129871A (OSRAM) |
| LU (1) | LU91220I2 (OSRAM) |
| MX (1) | MX9605391A (OSRAM) |
| MY (2) | MY149862A (OSRAM) |
| NL (1) | NL300216I2 (OSRAM) |
| NO (2) | NO315799B1 (OSRAM) |
| NZ (1) | NZ285510A (OSRAM) |
| PE (1) | PE23196A1 (OSRAM) |
| PL (1) | PL190540B1 (OSRAM) |
| PT (1) | PT758327E (OSRAM) |
| RU (1) | RU2139284C1 (OSRAM) |
| SI (1) | SI0758327T1 (OSRAM) |
| SK (1) | SK284407B6 (OSRAM) |
| TW (1) | TW504507B (OSRAM) |
| WO (1) | WO1995030670A2 (OSRAM) |
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| RU2234535C2 (ru) * | 2002-10-03 | 2004-08-20 | Государственный научный центр вирусологии и биотехнологии "Вектор" | Субстрат для определения активности интегразы вируса иммунодефицита человека |
| RU2246939C2 (ru) * | 2000-08-18 | 2005-02-27 | Контроль-Окс Ой | Полученные из растений синтетические фенольные соединения и растительные экстракты, эффективные при лечении и профилактике хламидийных инфекций |
| RU2434860C1 (ru) * | 2007-11-01 | 2011-11-27 | Ханми Холдингс Ко., Лтд. | Способ получения (6r)-3-гексил-4-гидрокси-6-ундецил-5,6-дигидропиран-2-она и промежуточного соединения, применяемого в данном способе |
| RU2509769C1 (ru) * | 2010-01-15 | 2014-03-20 | Ханми Сайенс Ко., Лтд. | Способ получения солей тетразолметансульфоновой кислоты и новое соединение, используемое в нем |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2246939C2 (ru) * | 2000-08-18 | 2005-02-27 | Контроль-Окс Ой | Полученные из растений синтетические фенольные соединения и растительные экстракты, эффективные при лечении и профилактике хламидийных инфекций |
| RU2234535C2 (ru) * | 2002-10-03 | 2004-08-20 | Государственный научный центр вирусологии и биотехнологии "Вектор" | Субстрат для определения активности интегразы вируса иммунодефицита человека |
| RU2434860C1 (ru) * | 2007-11-01 | 2011-11-27 | Ханми Холдингс Ко., Лтд. | Способ получения (6r)-3-гексил-4-гидрокси-6-ундецил-5,6-дигидропиран-2-она и промежуточного соединения, применяемого в данном способе |
| RU2509769C1 (ru) * | 2010-01-15 | 2014-03-20 | Ханми Сайенс Ко., Лтд. | Способ получения солей тетразолметансульфоновой кислоты и новое соединение, используемое в нем |
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