KR100445929B1 - 역전사바이러스감염을치료하기에유용한피라논화합물 - Google Patents

Info

Publication number

KR100445929B1

KR100445929B1 KR1019960706245A KR19960706245A KR100445929B1 KR 100445929 B1 KR100445929 B1 KR 100445929B1 KR 1019960706245 A KR1019960706245 A KR 1019960706245A KR 19960706245 A KR19960706245 A KR 19960706245A KR 100445929 B1 KR100445929 B1 KR 100445929B1

Authority

KR

South Korea

Prior art keywords

phenyl

hydroxy

propyl

pyran

oxo

Prior art date

1994-05-06

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.)

Expired - Lifetime

Links

• Espacenet
• Global Dossier
• Discuss

• ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical class O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 title abstract description 11
• 238000010839 reverse transcription Methods 0.000 title description 5
• 230000009385 viral infection Effects 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 714
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims abstract description 41
• -1 2 -cyclopropyl Chemical group 0.000 claims description 304
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 159
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 138
• 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 130
• 238000000034 method Methods 0.000 claims description 128
• 150000001412 amines Chemical class 0.000 claims description 91
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 73
• YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 47
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 43
• HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 claims description 42
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
• 229910000104 sodium hydride Inorganic materials 0.000 claims description 32
• 229940124530 sulfonamide Drugs 0.000 claims description 31
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
• 239000012312 sodium hydride Substances 0.000 claims description 29
• 150000001408 amides Chemical class 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 26
• 150000003839 salts Chemical class 0.000 claims description 23
• LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims description 22
• 239000003960 organic solvent Substances 0.000 claims description 21
• 150000007530 organic bases Chemical class 0.000 claims description 20
• 150000003456 sulfonamides Chemical class 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 19
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
• CWWWHACKSNBBMU-UHFFFAOYSA-N 1-phenylhexan-3-one Chemical compound CCCC(=O)CCC1=CC=CC=C1 CWWWHACKSNBBMU-UHFFFAOYSA-N 0.000 claims description 17
• 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 17
• 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 16
• 239000011734 sodium Substances 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 125000003037 imidazol-2-yl group Chemical group [H]N1C([*])=NC([H])=C1[H] 0.000 claims description 10
• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
• 229910052717 sulfur Chemical group 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
• 125000002619 bicyclic group Chemical group 0.000 claims description 7
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 239000001301 oxygen Chemical group 0.000 claims description 6
• 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 6
• 229920006395 saturated elastomer Polymers 0.000 claims description 6
• 239000011593 sulfur Chemical group 0.000 claims description 6
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 6
• 125000004260 quinazolin-2-yl group Chemical group [H]C1=NC(*)=NC2=C1C([H])=C([H])C([H])=C2[H] 0.000 claims description 5
• 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 4
• 239000004475 Arginine Substances 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 class 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
• YUCPJAAJLZXQOZ-UHFFFAOYSA-N n-[3-[cyclopropyl-(4-hydroxy-6-oxo-2,2-dipropyl-3h-pyran-5-yl)methyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound O=C1OC(CCC)(CCC)CC(O)=C1C(C=1C=C(NS(=O)(=O)C=2N=CN(C)C=2)C=CC=1)C1CC1 YUCPJAAJLZXQOZ-UHFFFAOYSA-N 0.000 claims description 4
• 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
• 229910052708 sodium Inorganic materials 0.000 claims description 4
• 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
• SQGDXPMEKOVUNE-UHFFFAOYSA-N N-[3-[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]propyl]phenyl]pyridine-2-sulfonamide Chemical class 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=NC=CC=C1 SQGDXPMEKOVUNE-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• LRGGJJZCDSKECU-UHFFFAOYSA-N n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-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=CC=C1 LRGGJJZCDSKECU-UHFFFAOYSA-N 0.000 claims description 3
• NCNJJWLCPJVLFO-UHFFFAOYSA-N n-[3-[[6-(1-azidopentan-3-yl)-4-hydroxy-2-oxopyran-3-yl]-cyclopropylmethyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound O=C1OC(C(CCN=[N+]=[N-])CC)=CC(O)=C1C(C=1C=C(NS(=O)(=O)C=2N=CN(C)C=2)C=CC=1)C1CC1 NCNJJWLCPJVLFO-UHFFFAOYSA-N 0.000 claims description 3
• SMABGRXWDGFPEH-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-6-[1-(2-methoxyethoxy)pentan-3-yl]-2-oxopyran-3-yl]methyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound O=C1OC(C(CCOCCOC)CC)=CC(O)=C1C(C=1C=C(NS(=O)(=O)C=2N=CN(C)C=2)C=CC=1)C1CC1 SMABGRXWDGFPEH-UHFFFAOYSA-N 0.000 claims description 3
• MEMPZWYMKIENFT-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-6-[3-(2-methoxyethoxy)propyl]-2-oxopyran-3-yl]methyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound O=C1OC(CCCOCCOC)=CC(O)=C1C(C=1C=C(NS(=O)(=O)C=2N=CN(C)C=2)C=CC=1)C1CC1 MEMPZWYMKIENFT-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
• 125000004542 purin-6-yl group Chemical group N1=CN=C2N=CNC2=C1* 0.000 claims description 3
• 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 3
• GXKMYJQDLNOGEO-UHFFFAOYSA-N 2-[[8-[3-[5-[[3-(1h-benzimidazol-2-ylsulfonylamino)phenyl]-cyclopropylmethyl]-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=2NC3=CC=CC=C3N=2)C=CC=1)C1CC1 GXKMYJQDLNOGEO-UHFFFAOYSA-N 0.000 claims description 2
• RCXIREKFNVGMOU-UHFFFAOYSA-N 2-[[8-[3-[5-[[3-(benzenesulfonamido)phenyl]-cyclopropylmethyl]-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=2C=CC=CC=2)C=CC=1)C1CC1 RCXIREKFNVGMOU-UHFFFAOYSA-N 0.000 claims description 2
• GBTHKYAWGLPMIY-UHFFFAOYSA-N 2-[[8-[3-[5-[cyclopropyl-[3-(1h-imidazol-2-ylsulfonylamino)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=2NC=CN=2)C=CC=1)C1CC1 GBTHKYAWGLPMIY-UHFFFAOYSA-N 0.000 claims description 2
• QIMFNOLWNIZKPD-UHFFFAOYSA-N 2-[[8-[3-[5-[cyclopropyl-[3-(pyridin-2-ylsulfonylamino)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=CC=CC=2)C=CC=1)C1CC1 QIMFNOLWNIZKPD-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• DNORAKKFDCRISV-UHFFFAOYSA-N 2-amino-4-[5-[[3-(1h-benzimidazol-2-ylsulfonylamino)phenyl]-cyclopropylmethyl]-4-hydroxy-6-oxopyran-2-yl]-n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]butanamide Chemical compound O=C1OC(CCC(N)C(=O)NC(CO)(CO)CO)=CC(O)=C1C(C=1C=C(NS(=O)(=O)C=2NC3=CC=CC=C3N=2)C=CC=1)C1CC1 DNORAKKFDCRISV-UHFFFAOYSA-N 0.000 claims description 2
• PGNAOHBVNAJYEW-UHFFFAOYSA-N 2-amino-4-[5-[[3-(benzenesulfonamido)phenyl]-cyclopropylmethyl]-4-hydroxy-6-oxopyran-2-yl]-n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]butanamide Chemical compound O=C1OC(CCC(N)C(=O)NC(CO)(CO)CO)=CC(O)=C1C(C=1C=C(NS(=O)(=O)C=2C=CC=CC=2)C=CC=1)C1CC1 PGNAOHBVNAJYEW-UHFFFAOYSA-N 0.000 claims description 2
• HMMHGRFNCAEMNU-UHFFFAOYSA-N 2-amino-4-[5-[cyclopropyl-[3-(1h-imidazol-2-ylsulfonylamino)phenyl]methyl]-4-hydroxy-6-oxopyran-2-yl]-n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]butanamide Chemical compound O=C1OC(CCC(N)C(=O)NC(CO)(CO)CO)=CC(O)=C1C(C=1C=C(NS(=O)(=O)C=2NC=CN=2)C=CC=1)C1CC1 HMMHGRFNCAEMNU-UHFFFAOYSA-N 0.000 claims description 2
• GBAZMVQISXHWIM-UHFFFAOYSA-N 2-amino-4-[5-[cyclopropyl-[3-(pyridin-2-ylsulfonylamino)phenyl]methyl]-4-hydroxy-6-oxopyran-2-yl]-n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]butanamide Chemical compound O=C1OC(CCC(N)C(=O)NC(CO)(CO)CO)=CC(O)=C1C(C=1C=C(NS(=O)(=O)C=2N=CC=CC=2)C=CC=1)C1CC1 GBAZMVQISXHWIM-UHFFFAOYSA-N 0.000 claims description 2
• WWNMOZIYEKNROH-UHFFFAOYSA-N 2-amino-4-[5-[cyclopropyl-[3-[(1-methylimidazol-2-yl)sulfonylamino]phenyl]methyl]-4-hydroxy-6-oxopyran-2-yl]-n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]butanamide Chemical compound CN1C=CN=C1S(=O)(=O)NC1=CC=CC(C(C2CC2)C=2C(OC(CCC(N)C(=O)NC(CO)(CO)CO)=CC=2O)=O)=C1 WWNMOZIYEKNROH-UHFFFAOYSA-N 0.000 claims description 2
• ZISVMKCDIYWPEX-UHFFFAOYSA-N 2-amino-4-[5-[cyclopropyl-[3-[(1-methylimidazol-4-yl)sulfonylamino]phenyl]methyl]-4-hydroxy-6-oxopyran-2-yl]-n-[1,3-dihydroxy-2-(hydroxymethyl)propan-2-yl]butanamide Chemical compound CN1C=NC(S(=O)(=O)NC=2C=C(C=CC=2)C(C2CC2)C=2C(OC(CCC(N)C(=O)NC(CO)(CO)CO)=CC=2O)=O)=C1 ZISVMKCDIYWPEX-UHFFFAOYSA-N 0.000 claims description 2
• SGXGYLDRGBWXKW-UHFFFAOYSA-N 2-hydroxy-N-[3-[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]propyl]phenyl]benzenesulfonamide Chemical compound C=1C=CC(NS(=O)(=O)C=2C(=CC=CC=2)O)=CC=1C(CC)C(C(O1)CC=O)=C(O)CC1(C=1C=CC=CC=1)C1=CC=CC=C1 SGXGYLDRGBWXKW-UHFFFAOYSA-N 0.000 claims description 2
• MFHNQRLMXNAAHA-UHFFFAOYSA-N 2-hydroxy-n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]propyl]phenyl]benzenesulfonamide Chemical compound C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3C(=CC=CC=3)O)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 MFHNQRLMXNAAHA-UHFFFAOYSA-N 0.000 claims description 2
• LDRYFGXDYMMYIR-UHFFFAOYSA-N 3-[[3-(1h-benzimidazol-2-ylsulfonylmethyl)phenyl]-cyclopropylmethyl]-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=3NC4=CC=CC=C4N=3)C=CC=2)C(=O)OC=1C(CC)CC1=CC=CC=C1 LDRYFGXDYMMYIR-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
• 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
• 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
• 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
• ILSIUSIHKBGUQT-UHFFFAOYSA-N 4-[[3-[cyclopropyl-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]methyl]phenyl]methylsulfonyl]benzonitrile Chemical compound C1C(O)=C(C(C2CC2)C=2C=C(CS(=O)(=O)C=3C=CC(=CC=3)C#N)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 ILSIUSIHKBGUQT-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
• SWZRJQGYMCZICW-UHFFFAOYSA-N 4-cyano-n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]propyl]phenyl]benzenesulfonamide Chemical compound C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3C=CC(=CC=3)C#N)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 SWZRJQGYMCZICW-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
• BIDDTDOVRMYYOL-UHFFFAOYSA-N 4-cyano-n-[3-[[1-(4-hydroxy-6-oxo-2,2-dipropyl-3h-pyran-5-yl)cyclopropyl]methyl]phenyl]benzenesulfonamide Chemical compound O=C1OC(CCC)(CCC)CC(O)=C1C1(CC=2C=C(NS(=O)(=O)C=3C=CC(=CC=3)C#N)C=CC=2)CC1 BIDDTDOVRMYYOL-UHFFFAOYSA-N 0.000 claims description 2
• ZVOJZKFASJFZKR-UHFFFAOYSA-N 4-cyano-n-[3-[[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]cyclopropyl]methyl]phenyl]benzenesulfonamide Chemical compound C1C(O)=C(C2(CC=3C=C(NS(=O)(=O)C=4C=CC(=CC=4)C#N)C=CC=3)CC2)C(=O)OC1(CCC)CCC1=CC=CC=C1 ZVOJZKFASJFZKR-UHFFFAOYSA-N 0.000 claims description 2
• GDZNOQJDTRZGEW-UHFFFAOYSA-N 4-cyano-n-[3-[cyclopropyl-[6-(1,3-dicyclopropylpropan-2-yl)-4-hydroxy-2-oxopyran-3-yl]methyl]phenyl]benzenesulfonamide Chemical compound OC=1C=C(C(CC2CC2)CC2CC2)OC(=O)C=1C(C=1C=C(NS(=O)(=O)C=2C=CC(=CC=2)C#N)C=CC=1)C1CC1 GDZNOQJDTRZGEW-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
• QGDDBHANGIGIBF-UHFFFAOYSA-N 4-fluoro-n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]propyl]phenyl]benzenesulfonamide Chemical compound C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3C=CC(F)=CC=3)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 QGDDBHANGIGIBF-UHFFFAOYSA-N 0.000 claims description 2
• UMQSERHFVBTSHI-UHFFFAOYSA-N 4-fluoro-n-[3-[[1-(4-hydroxy-6-oxo-2,2-dipropyl-3h-pyran-5-yl)cyclopropyl]methyl]phenyl]benzenesulfonamide Chemical compound O=C1OC(CCC)(CCC)CC(O)=C1C1(CC=2C=C(NS(=O)(=O)C=3C=CC(F)=CC=3)C=CC=2)CC1 UMQSERHFVBTSHI-UHFFFAOYSA-N 0.000 claims description 2
• NKOAJBMTRIVPEL-UHFFFAOYSA-N 4-fluoro-n-[3-[[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]cyclopropyl]methyl]phenyl]benzenesulfonamide Chemical compound C1C(O)=C(C2(CC=3C=C(NS(=O)(=O)C=4C=CC(F)=CC=4)C=CC=3)CC2)C(=O)OC1(CCC)CCC1=CC=CC=C1 NKOAJBMTRIVPEL-UHFFFAOYSA-N 0.000 claims description 2
• OLWLCHNARYYQLL-UHFFFAOYSA-N 5-[[3-(1h-benzimidazol-2-ylsulfonylmethyl)phenyl]-cyclopropylmethyl]-4-hydroxy-2-(2-phenylethyl)-2-propyl-3h-pyran-6-one Chemical compound C1C(O)=C(C(C2CC2)C=2C=C(CS(=O)(=O)C=3NC4=CC=CC=C4N=3)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 OLWLCHNARYYQLL-UHFFFAOYSA-N 0.000 claims description 2
• CKXVIVGYYRBBHS-UHFFFAOYSA-N 5-[cyclopropyl-[3-(pyridin-2-ylsulfonylmethyl)phenyl]methyl]-4-hydroxy-2-(2-phenylethyl)-2-propyl-3h-pyran-6-one Chemical compound C1C(O)=C(C(C2CC2)C=2C=C(CS(=O)(=O)C=3N=CC=CC=3)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 CKXVIVGYYRBBHS-UHFFFAOYSA-N 0.000 claims description 2
• OKRUIZYMAASPEW-UHFFFAOYSA-N 5-[cyclopropyl-[3-(quinolin-2-ylsulfonylmethyl)phenyl]methyl]-4-hydroxy-2-(2-phenylethyl)-2-propyl-3h-pyran-6-one Chemical compound C1C(O)=C(C(C2CC2)C=2C=C(CS(=O)(=O)C=3N=C4C=CC=CC4=CC=3)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 OKRUIZYMAASPEW-UHFFFAOYSA-N 0.000 claims description 2
• UFXRKZRLUCJDMS-UHFFFAOYSA-N 5-[cyclopropyl-[3-[(1-methylimidazol-4-yl)sulfonylmethyl]phenyl]methyl]-4-hydroxy-2-(2-phenylethyl)-2-propyl-3h-pyran-6-one Chemical compound C1C(O)=C(C(C2CC2)C=2C=C(CS(=O)(=O)C=3N=CN(C)C=3)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 UFXRKZRLUCJDMS-UHFFFAOYSA-N 0.000 claims description 2
• HWABYPZESASKHA-UHFFFAOYSA-N 5-amino-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(N)=CC=3)C=CC=2)C(C)(C)C)C(=O)OC1(CCC)CCC1=CC=CC=C1 HWABYPZESASKHA-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
• GDRVMXLZKTVRPW-UHFFFAOYSA-N 5-cyano-n-[3-[[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]cyclopropyl]methyl]phenyl]pyridine-2-sulfonamide Chemical compound C1C(O)=C(C2(CC=3C=C(NS(=O)(=O)C=4N=CC(=CC=4)C#N)C=CC=3)CC2)C(=O)OC1(CCC)CCC1=CC=CC=C1 GDRVMXLZKTVRPW-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
• LMXJIEIILMMLEV-UHFFFAOYSA-N 6-[[3-[cyclopropyl-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]methyl]phenyl]methylsulfonyl]pyridine-3-carbonitrile Chemical compound C1C(O)=C(C(C2CC2)C=2C=C(CS(=O)(=O)C=3N=CC(=CC=3)C#N)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 LMXJIEIILMMLEV-UHFFFAOYSA-N 0.000 claims description 2
• 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 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
• 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
• OQQKVZCEDMNGFL-UHFFFAOYSA-N N-[3-[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]propyl]phenyl]quinoline-2-sulfonamide Chemical class 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=C1 OQQKVZCEDMNGFL-UHFFFAOYSA-N 0.000 claims description 2
• 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
• 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 description 2
• 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 description 2
• POQVBFPMVPCJQU-UHFFFAOYSA-N n-[3-[1-(4-hydroxy-6-oxo-2,2-dipropyl-3h-pyran-5-yl)propyl]phenyl]-1-methylimidazole-2-sulfonamide Chemical compound O=C1OC(CCC)(CCC)CC(O)=C1C(CC)C1=CC=CC(NS(=O)(=O)C=2N(C=CN=2)C)=C1 POQVBFPMVPCJQU-UHFFFAOYSA-N 0.000 claims description 2
• OWBIZTIQPYOOFG-UHFFFAOYSA-N n-[3-[1-(4-hydroxy-6-oxo-2,2-dipropyl-3h-pyran-5-yl)propyl]phenyl]-5-(trifluoromethyl)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(F)(F)F)=C1 OWBIZTIQPYOOFG-UHFFFAOYSA-N 0.000 claims description 2
• STHZIMXCCJAYPV-UHFFFAOYSA-N n-[3-[1-[2,2-bis(2-cyclopropylethyl)-4-hydroxy-6-oxo-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(C=2C(OC(CCC3CC3)(CCC3CC3)CC=2O)=O)C(C)(C)C)=C1 STHZIMXCCJAYPV-UHFFFAOYSA-N 0.000 claims description 2
• DBAWJUWUDIYVHA-UHFFFAOYSA-N n-[3-[1-[2,2-bis(2-cyclopropylethyl)-4-hydroxy-6-oxo-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]-5-cyanopyridine-2-sulfonamide Chemical compound C=1C=CC(NS(=O)(=O)C=2N=CC(=CC=2)C#N)=CC=1C(C(C)(C)C)C(C(O1)=O)=C(O)CC1(CCC1CC1)CCC1CC1 DBAWJUWUDIYVHA-UHFFFAOYSA-N 0.000 claims description 2
• HTPISUBBGCZOAD-UHFFFAOYSA-N n-[3-[1-[2,2-bis(2-cyclopropylethyl)-4-hydroxy-6-oxo-3h-pyran-5-yl]propyl]phenyl]-5-cyanopyridine-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(CCC1CC1)CCC1CC1 HTPISUBBGCZOAD-UHFFFAOYSA-N 0.000 claims description 2
• XQKQUSXNGYFKPN-UHFFFAOYSA-N n-[3-[1-[2,2-bis[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-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(C=2C(OC(CCC=3C=CC(F)=CC=3)(CCC=3C=CC(F)=CC=3)CC=2O)=O)C(C)(C)C)=C1 XQKQUSXNGYFKPN-UHFFFAOYSA-N 0.000 claims description 2
• NXRXXYMKHLULPS-UHFFFAOYSA-N n-[3-[1-[2,2-bis[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]-5-cyanopyridine-2-sulfonamide Chemical compound C=1C=CC(NS(=O)(=O)C=2N=CC(=CC=2)C#N)=CC=1C(C(C)(C)C)C(C(O1)=O)=C(O)CC1(CCC=1C=CC(F)=CC=1)CCC1=CC=C(F)C=C1 NXRXXYMKHLULPS-UHFFFAOYSA-N 0.000 claims description 2
• MMRSADPBHVYOMB-UHFFFAOYSA-N n-[3-[1-[2,2-bis[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-3h-pyran-5-yl]propyl]phenyl]-5-cyanopyridine-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(F)=CC=1)CCC1=CC=C(F)C=C1 MMRSADPBHVYOMB-UHFFFAOYSA-N 0.000 claims description 2
• KTNLOHRAKZKWJY-UHFFFAOYSA-N n-[3-[1-[4-hydroxy-2,2-bis(2-methylpropyl)-6-oxo-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)C1=C(O)CC(CC(C)C)(CC(C)C)OC1=O KTNLOHRAKZKWJY-UHFFFAOYSA-N 0.000 claims description 2
• ZUUVMQIINQIUJN-UHFFFAOYSA-N n-[3-[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(C=2C(OC(CCC=3C=CC=CC=3)(CCC=3C=CC=CC=3)CC=2O)=O)C(C)(C)C)=C1 ZUUVMQIINQIUJN-UHFFFAOYSA-N 0.000 claims description 2
• ZXVYHEJQODFGMG-UHFFFAOYSA-N n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]-5-(trifluoromethyl)pyridine-2-sulfonamide Chemical compound C1C(O)=C(C(C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C(F)(F)F)C=CC=2)C(C)(C)C)C(=O)OC1(CCC)CCC1=CC=CC=C1 ZXVYHEJQODFGMG-UHFFFAOYSA-N 0.000 claims description 2
• JDMBZFDXSJNJBR-UHFFFAOYSA-N n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]propyl]phenyl]-1h-benzimidazole-2-sulfonamide Chemical compound C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3NC4=CC=CC=C4N=3)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 JDMBZFDXSJNJBR-UHFFFAOYSA-N 0.000 claims description 2
• DWAKAIVTTURURI-UHFFFAOYSA-N n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]propyl]phenyl]-1h-imidazole-2-sulfonamide Chemical compound C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3NC=CN=3)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 DWAKAIVTTURURI-UHFFFAOYSA-N 0.000 claims description 2
• LHJAZWYHUGBTPG-UHFFFAOYSA-N 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=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 LHJAZWYHUGBTPG-UHFFFAOYSA-N 0.000 claims description 2
• GGQQHVCYJSFAGB-UHFFFAOYSA-N n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]propyl]phenyl]pyrimidine-2-sulfonamide Chemical class C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3N=CC=CN=3)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 GGQQHVCYJSFAGB-UHFFFAOYSA-N 0.000 claims description 2
• HLWQGRRCLANAKK-UHFFFAOYSA-N n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]propyl]phenyl]quinazoline-2-sulfonamide Chemical compound C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3N=C4C=CC=CC4=CN=3)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 HLWQGRRCLANAKK-UHFFFAOYSA-N 0.000 claims description 2
• NLLYRTWTRUOUPU-UHFFFAOYSA-N n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]propyl]phenyl]quinoline-2-sulfonamide Chemical compound C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3N=C4C=CC=CC4=CC=3)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 NLLYRTWTRUOUPU-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• YWLXOKIDWGNROL-UHFFFAOYSA-N n-[3-[[1-(4-hydroxy-6-oxo-2,2-dipropyl-3h-pyran-5-yl)cyclopropyl]methyl]phenyl]-1-methylimidazole-2-sulfonamide Chemical compound O=C1OC(CCC)(CCC)CC(O)=C1C1(CC=2C=C(NS(=O)(=O)C=3N(C=CN=3)C)C=CC=2)CC1 YWLXOKIDWGNROL-UHFFFAOYSA-N 0.000 claims description 2
• AZGVOSYLGHXCEI-UHFFFAOYSA-N n-[3-[[1-(4-hydroxy-6-oxo-2,2-dipropyl-3h-pyran-5-yl)cyclopropyl]methyl]phenyl]quinoline-8-sulfonamide Chemical compound O=C1OC(CCC)(CCC)CC(O)=C1C1(CC=2C=C(NS(=O)(=O)C=3C4=NC=CC=C4C=CC=3)C=CC=2)CC1 AZGVOSYLGHXCEI-UHFFFAOYSA-N 0.000 claims description 2
• FQUQZZPGDBBICT-UHFFFAOYSA-N n-[3-[[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]cyclopropyl]methyl]phenyl]quinoline-8-sulfonamide Chemical compound C1C(O)=C(C2(CC=3C=C(NS(=O)(=O)C=4C5=NC=CC=C5C=CC=4)C=CC=3)CC2)C(=O)OC1(CCC)CCC1=CC=CC=C1 FQUQZZPGDBBICT-UHFFFAOYSA-N 0.000 claims description 2
• FMGIFZHIZCBFOH-UHFFFAOYSA-N n-[3-[[6-(1-bromopentan-3-yl)-4-hydroxy-2-oxopyran-3-yl]-cyclopropylmethyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound O=C1OC(C(CCBr)CC)=CC(O)=C1C(C=1C=C(NS(=O)(=O)C=2N=CN(C)C=2)C=CC=1)C1CC1 FMGIFZHIZCBFOH-UHFFFAOYSA-N 0.000 claims description 2
• PTWNQUJNIAXYOG-UHFFFAOYSA-N n-[3-[[6-(3-amino-4-oxo-4-piperazin-1-ylbutyl)-4-hydroxy-2-oxopyran-3-yl]-cyclopropylmethyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NC=2C=C(C=CC=2)C(C2CC2)C=2C(OC(CCC(N)C(=O)N3CCNCC3)=CC=2O)=O)=C1 PTWNQUJNIAXYOG-UHFFFAOYSA-N 0.000 claims description 2
• YJSJMNIKVCUWDC-UHFFFAOYSA-N n-[3-[[6-(3-amino-4-oxo-4-piperazin-1-ylbutyl)-4-hydroxy-2-oxopyran-3-yl]-cyclopropylmethyl]phenyl]-1h-benzimidazole-2-sulfonamide Chemical compound C1CNCCN1C(=O)C(N)CCC(OC1=O)=CC(O)=C1C(C=1C=C(NS(=O)(=O)C=2NC3=CC=CC=C3N=2)C=CC=1)C1CC1 YJSJMNIKVCUWDC-UHFFFAOYSA-N 0.000 claims description 2
• NJUWPHKTNYTYNC-UHFFFAOYSA-N n-[3-[[6-(3-amino-4-oxo-4-piperazin-1-ylbutyl)-4-hydroxy-2-oxopyran-3-yl]-cyclopropylmethyl]phenyl]-1h-imidazole-2-sulfonamide Chemical compound C1CNCCN1C(=O)C(N)CCC(OC1=O)=CC(O)=C1C(C=1C=C(NS(=O)(=O)C=2NC=CN=2)C=CC=1)C1CC1 NJUWPHKTNYTYNC-UHFFFAOYSA-N 0.000 claims description 2
• UFUNCSXWIHOGDD-UHFFFAOYSA-N n-[3-[[6-(3-amino-4-oxo-4-piperazin-1-ylbutyl)-4-hydroxy-2-oxopyran-3-yl]-cyclopropylmethyl]phenyl]benzenesulfonamide Chemical compound C1CNCCN1C(=O)C(N)CCC(OC1=O)=CC(O)=C1C(C=1C=C(NS(=O)(=O)C=2C=CC=CC=2)C=CC=1)C1CC1 UFUNCSXWIHOGDD-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• IMXXWUHDQINZEB-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-(1,3-dicyclopropylpropan-2-yl)-4-hydroxy-2-oxopyran-3-yl]methyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NC=2C=C(C=CC=2)C(C2CC2)C=2C(OC(=CC=2O)C(CC2CC2)CC2CC2)=O)=C1 IMXXWUHDQINZEB-UHFFFAOYSA-N 0.000 claims description 2
• XRPZKASTWDGNNY-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-(1,3-dicyclopropylpropan-2-yl)-4-hydroxy-2-oxopyran-3-yl]methyl]phenyl]-1h-benzimidazole-2-sulfonamide Chemical compound OC=1C=C(C(CC2CC2)CC2CC2)OC(=O)C=1C(C=1C=C(NS(=O)(=O)C=2NC3=CC=CC=C3N=2)C=CC=1)C1CC1 XRPZKASTWDGNNY-UHFFFAOYSA-N 0.000 claims description 2
• 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
• CEJNKMWDOPFONI-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-(1,3-dicyclopropylpropan-2-yl)-4-hydroxy-2-oxopyran-3-yl]methyl]phenyl]pyridine-2-sulfonamide Chemical compound OC=1C=C(C(CC2CC2)CC2CC2)OC(=O)C=1C(C=1C=C(NS(=O)(=O)C=2N=CC=CC=2)C=CC=1)C1CC1 CEJNKMWDOPFONI-UHFFFAOYSA-N 0.000 claims description 2
• MCFYFXLHBQVALW-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-(1,3-dicyclopropylpropan-2-yl)-4-hydroxy-2-oxopyran-3-yl]methyl]phenyl]quinoline-2-sulfonamide Chemical compound OC=1C=C(C(CC2CC2)CC2CC2)OC(=O)C=1C(C=1C=C(NS(=O)(=O)C=2N=C3C=CC=CC3=CC=2)C=CC=1)C1CC1 MCFYFXLHBQVALW-UHFFFAOYSA-N 0.000 claims description 2
• HJKNBMVMDDGJBX-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-(1,3-dicyclopropylpropan-2-yl)-4-hydroxy-2-oxopyran-3-yl]methyl]phenyl]quinoline-8-sulfonamide Chemical compound OC=1C=C(C(CC2CC2)CC2CC2)OC(=O)C=1C(C=1C=C(NS(=O)(=O)C=2C3=NC=CC=C3C=CC=2)C=CC=1)C1CC1 HJKNBMVMDDGJBX-UHFFFAOYSA-N 0.000 claims description 2
• 239000011591 potassium Substances 0.000 claims description 2
• 229910052700 potassium Inorganic materials 0.000 claims description 2
• ZHDLFKICABABHZ-OAQYLSRUSA-N 5-cyano-n-[3-[(1r)-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)=C1[C@H](CC)C1=CC=CC(NS(=O)(=O)C=2N=CC(=CC=2)C#N)=C1 ZHDLFKICABABHZ-OAQYLSRUSA-N 0.000 claims 2
• WSBWKGLVMNROFG-MXBOTTGLSA-N 5-cyano-n-[3-[(1r)-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-MXBOTTGLSA-N 0.000 claims 2
• WSBWKGLVMNROFG-NEEKEDPPSA-N 5-cyano-n-[3-[(1r)-1-[(2s)-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-NEEKEDPPSA-N 0.000 claims 2
• ZHDLFKICABABHZ-NRFANRHFSA-N 5-cyano-n-[3-[(1s)-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)=C1[C@@H](CC)C1=CC=CC(NS(=O)(=O)C=2N=CC(=CC=2)C#N)=C1 ZHDLFKICABABHZ-NRFANRHFSA-N 0.000 claims 2
• 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
• WSBWKGLVMNROFG-HVNZXBJASA-N 5-cyano-n-[3-[(1s)-1-[(2s)-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-HVNZXBJASA-N 0.000 claims 2
• 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 2
• 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
• 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
• GBUAPDRALQGUKR-UHFFFAOYSA-N 4-cyano-n-[3-[1-[2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]benzenesulfonamide Chemical compound C1C(O)=C(C(C=2C=C(NS(=O)(=O)C=3C=CC(=CC=3)C#N)C=CC=2)C(C)(C)C)C(=O)OC1(CCC)CCC1=CC=C(F)C=C1 GBUAPDRALQGUKR-UHFFFAOYSA-N 0.000 claims 1
• HDLWNHFOXFISPE-UHFFFAOYSA-N 4-cyano-n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]benzenesulfonamide Chemical compound C1C(O)=C(C(C=2C=C(NS(=O)(=O)C=3C=CC(=CC=3)C#N)C=CC=2)C(C)(C)C)C(=O)OC1(CCC)CCC1=CC=CC=C1 HDLWNHFOXFISPE-UHFFFAOYSA-N 0.000 claims 1
• INMRFNZVIREHTE-UHFFFAOYSA-N 4-cyano-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=C(C=3)C#N)C=CC=2)C(=O)OC=1C(CC)CC1CCOCC1 INMRFNZVIREHTE-UHFFFAOYSA-N 0.000 claims 1
• PCQDPJDQSPDYRT-UHFFFAOYSA-N 4-cyano-n-[3-[cyclopropyl-[6-[2-(1-ethylcyclohexa-2,4-dien-1-yl)ethyl]-4-hydroxy-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=C(C=3)C#N)C=CC=2)C(=O)OC=1CCC1(CC)CC=CC=C1 PCQDPJDQSPDYRT-UHFFFAOYSA-N 0.000 claims 1
• YLYCYASVEHAIKW-UHFFFAOYSA-N 4-fluoro-n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]benzenesulfonamide Chemical compound C1C(O)=C(C(C=2C=C(NS(=O)(=O)C=3C=CC(F)=CC=3)C=CC=2)C(C)(C)C)C(=O)OC1(CCC)CCC1=CC=CC=C1 YLYCYASVEHAIKW-UHFFFAOYSA-N 0.000 claims 1
• FOKFSZVDQCHCLO-HXUWFJFHSA-N 5-amino-n-[3-[(1r)-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)=C1[C@H](CC)C1=CC=CC(NS(=O)(=O)C=2N=CC(N)=CC=2)=C1 FOKFSZVDQCHCLO-HXUWFJFHSA-N 0.000 claims 1
• BMETUISQRLGOBS-FYBSXPHGSA-N 5-amino-n-[3-[(1r)-1-[(2r)-2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-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(N)=CC=3)C=CC=2)=C(O)C1)CC1=CC=C(F)C=C1 BMETUISQRLGOBS-FYBSXPHGSA-N 0.000 claims 1
• FECIOCANKOYOJB-UUWRZZSWSA-N 5-amino-n-[3-[(1r)-1-[4-hydroxy-6-oxo-2,2-bis(2-phenylethyl)-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]pyridine-2-sulfonamide Chemical compound O1C(=O)C([C@H](C(C)(C)C)C=2C=C(NS(=O)(=O)C=3N=CC(N)=CC=3)C=CC=2)=C(O)CC1(CCC=1C=CC=CC=1)CCC1=CC=CC=C1 FECIOCANKOYOJB-UUWRZZSWSA-N 0.000 claims 1
• FOKFSZVDQCHCLO-FQEVSTJZSA-N 5-amino-n-[3-[(1s)-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)=C1[C@@H](CC)C1=CC=CC(NS(=O)(=O)C=2N=CC(N)=CC=2)=C1 FOKFSZVDQCHCLO-FQEVSTJZSA-N 0.000 claims 1
• BMETUISQRLGOBS-SETSBSEESA-N 5-amino-n-[3-[(1s)-1-[(2r)-2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-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(N)=CC=3)C=CC=2)=C(O)C1)CC1=CC=C(F)C=C1 BMETUISQRLGOBS-SETSBSEESA-N 0.000 claims 1
• BMETUISQRLGOBS-QCDSWUKFSA-N 5-amino-n-[3-[(1s)-1-[(2s)-2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-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(N)=CC=3)C=CC=2)=C(O)C1)CC1=CC=C(F)C=C1 BMETUISQRLGOBS-QCDSWUKFSA-N 0.000 claims 1
• FECIOCANKOYOJB-UMSFTDKQSA-N 5-amino-n-[3-[(1s)-1-[4-hydroxy-6-oxo-2,2-bis(2-phenylethyl)-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]pyridine-2-sulfonamide Chemical compound O1C(=O)C([C@@H](C(C)(C)C)C=2C=C(NS(=O)(=O)C=3N=CC(N)=CC=3)C=CC=2)=C(O)CC1(CCC=1C=CC=CC=1)CCC1=CC=CC=C1 FECIOCANKOYOJB-UMSFTDKQSA-N 0.000 claims 1
• IGCNVWGAMZYNBE-UHFFFAOYSA-N 5-amino-n-[3-[[4-hydroxy-6-oxo-2,2-bis(2-phenylethyl)-3h-pyran-5-yl]methyl]phenyl]pyridine-2-sulfonamide Chemical compound N1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC(CC=2C(OC(CCC=3C=CC=CC=3)(CCC=3C=CC=CC=3)CC=2O)=O)=C1 IGCNVWGAMZYNBE-UHFFFAOYSA-N 0.000 claims 1
• XASDPKAWLITCOY-UHFFFAOYSA-N 5-cyano-N-[3-[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]propyl]phenyl]-N-methylpyridine-2-sulfonamide Chemical compound C(#N)C=1C=CC(=NC=1)S(=O)(=O)N(C)C1=CC(=CC=C1)C(CC)C=1C(OC(CC=1O)(C1=CC=CC=C1)C1=CC=CC=C1)CC=O XASDPKAWLITCOY-UHFFFAOYSA-N 0.000 claims 1
• YIIKDYADFBAUNX-LXANVCGNSA-N 5-cyano-n-[3-[(1r)-1-[(2r)-2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]pyridine-2-sulfonamide Chemical compound C([C@@]1(CCC)OC(=O)C([C@@H](C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C#N)C=CC=2)C(C)(C)C)=C(O)C1)CC1=CC=C(F)C=C1 YIIKDYADFBAUNX-LXANVCGNSA-N 0.000 claims 1
• FNGPDMVDSXJKKX-MXBOTTGLSA-N 5-cyano-n-[3-[(1r)-1-[(2r)-2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-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=C(F)C=C1 FNGPDMVDSXJKKX-MXBOTTGLSA-N 0.000 claims 1
• YIIKDYADFBAUNX-NDKRRWIDSA-N 5-cyano-n-[3-[(1r)-1-[(2s)-2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]pyridine-2-sulfonamide Chemical compound C([C@]1(CCC)OC(=O)C([C@@H](C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C#N)C=CC=2)C(C)(C)C)=C(O)C1)CC1=CC=C(F)C=C1 YIIKDYADFBAUNX-NDKRRWIDSA-N 0.000 claims 1
• FNGPDMVDSXJKKX-NEEKEDPPSA-N 5-cyano-n-[3-[(1r)-1-[(2s)-2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-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=C(F)C=C1 FNGPDMVDSXJKKX-NEEKEDPPSA-N 0.000 claims 1
• JUVYDGRKDAIDJB-PGUFJCEWSA-N 5-cyano-n-[3-[(1r)-1-[4-hydroxy-6-oxo-2,2-bis(2-phenylethyl)-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]pyridine-2-sulfonamide Chemical compound O1C(=O)C([C@H](C(C)(C)C)C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C#N)C=CC=2)=C(O)CC1(CCC=1C=CC=CC=1)CCC1=CC=CC=C1 JUVYDGRKDAIDJB-PGUFJCEWSA-N 0.000 claims 1
• YIIKDYADFBAUNX-BZKUTMRRSA-N 5-cyano-n-[3-[(1s)-1-[(2r)-2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]pyridine-2-sulfonamide Chemical compound C([C@@]1(CCC)OC(=O)C([C@H](C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C#N)C=CC=2)C(C)(C)C)=C(O)C1)CC1=CC=C(F)C=C1 YIIKDYADFBAUNX-BZKUTMRRSA-N 0.000 claims 1
• FNGPDMVDSXJKKX-SUYBVONHSA-N 5-cyano-n-[3-[(1s)-1-[(2r)-2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-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=C(F)C=C1 FNGPDMVDSXJKKX-SUYBVONHSA-N 0.000 claims 1
• YIIKDYADFBAUNX-DITALETJSA-N 5-cyano-n-[3-[(1s)-1-[(2s)-2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]pyridine-2-sulfonamide Chemical compound C([C@]1(CCC)OC(=O)C([C@H](C=2C=C(NS(=O)(=O)C=3N=CC(=CC=3)C#N)C=CC=2)C(C)(C)C)=C(O)C1)CC1=CC=C(F)C=C1 YIIKDYADFBAUNX-DITALETJSA-N 0.000 claims 1
• FNGPDMVDSXJKKX-HVNZXBJASA-N 5-cyano-n-[3-[(1s)-1-[(2s)-2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-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=C(F)C=C1 FNGPDMVDSXJKKX-HVNZXBJASA-N 0.000 claims 1
• AEIMLFGZRFRJQE-UHFFFAOYSA-N 5-cyano-n-[3-[1-[2-[3-[(5-cyanopyridin-2-yl)sulfonylamino]phenyl]-2-ethyl-4-hydroxy-6-oxo-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(CC)C(C=1)=CC=CC=1NS(=O)(=O)C1=CC=C(C#N)C=N1 AEIMLFGZRFRJQE-UHFFFAOYSA-N 0.000 claims 1
• QJPCHBQDKXQNOX-UHFFFAOYSA-N 5-cyano-n-[3-[1-[4-hydroxy-2,2-bis(2-methylpropyl)-6-oxo-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)C1=C(O)CC(CC(C)C)(CC(C)C)OC1=O QJPCHBQDKXQNOX-UHFFFAOYSA-N 0.000 claims 1
• JUVYDGRKDAIDJB-UHFFFAOYSA-N 5-cyano-n-[3-[1-[4-hydroxy-6-oxo-2,2-bis(2-phenylethyl)-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]pyridine-2-sulfonamide Chemical compound C=1C=CC(NS(=O)(=O)C=2N=CC(=CC=2)C#N)=CC=1C(C(C)(C)C)C(C(O1)=O)=C(O)CC1(CCC=1C=CC=CC=1)CCC1=CC=CC=C1 JUVYDGRKDAIDJB-UHFFFAOYSA-N 0.000 claims 1
• KLHPCSQWFNGGCD-UHFFFAOYSA-N 5-cyano-n-[3-[[4-hydroxy-6-oxo-2,2-bis(2-phenylethyl)-3h-pyran-5-yl]methyl]phenyl]pyridine-2-sulfonamide Chemical compound O=C1OC(CCC=2C=CC=CC=2)(CCC=2C=CC=CC=2)CC(O)=C1CC(C=1)=CC=CC=1NS(=O)(=O)C1=CC=C(C#N)C=N1 KLHPCSQWFNGGCD-UHFFFAOYSA-N 0.000 claims 1
• 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
• BJHHWJNGLZFNIV-UHFFFAOYSA-N N-[3-[1-[4-hydroxy-2-(2-oxoethyl)-6,6-diphenyl-2,5-dihydropyran-3-yl]propyl]phenyl]-N-methyl-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)N(S(=O)(=O)C=1N=CSC=1)C BJHHWJNGLZFNIV-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
• 206010041349 Somnolence Diseases 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
• 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
• 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
• 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
• 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
• LYUJJKJZIZRGMA-IZEXYCQBSA-N n-[3-[(1s)-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-IZEXYCQBSA-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
• 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
• JZESSUWNVVXDIK-UHFFFAOYSA-N n-[3-[1-[2,2-bis(2-cyclopropylethyl)-4-hydroxy-6-oxo-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(CCC1CC1)CCC1CC1 JZESSUWNVVXDIK-UHFFFAOYSA-N 0.000 claims 1
• UVNNNXSWZBCWHY-UHFFFAOYSA-N n-[3-[1-[2,2-bis[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-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(F)=CC=1)CCC1=CC=C(F)C=C1 UVNNNXSWZBCWHY-UHFFFAOYSA-N 0.000 claims 1
• YNDOWZZDZUXHHY-UHFFFAOYSA-N n-[3-[1-[2-[2-(4-fluorophenyl)ethyl]-4-hydroxy-6-oxo-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]quinoline-8-sulfonamide Chemical compound C1C(O)=C(C(C=2C=C(NS(=O)(=O)C=3C4=NC=CC=C4C=CC=3)C=CC=2)C(C)(C)C)C(=O)OC1(CCC)CCC1=CC=C(F)C=C1 YNDOWZZDZUXHHY-UHFFFAOYSA-N 0.000 claims 1
• 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
• OVIDFHASDQVWRA-UHFFFAOYSA-N n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]-2,2-dimethylpropyl]phenyl]quinoline-8-sulfonamide Chemical compound C1C(O)=C(C(C=2C=C(NS(=O)(=O)C=3C4=NC=CC=C4C=CC=3)C=CC=2)C(C)(C)C)C(=O)OC1(CCC)CCC1=CC=CC=C1 OVIDFHASDQVWRA-UHFFFAOYSA-N 0.000 claims 1
• JGCVAIGYLJWSRQ-UHFFFAOYSA-N n-[3-[1-[4-hydroxy-6-oxo-2-(2-phenylethyl)-2-propyl-3h-pyran-5-yl]propyl]phenyl]-7h-purine-6-sulfonamide Chemical compound C1C(O)=C(C(CC)C=2C=C(NS(=O)(=O)C=3C=4NC=NC=4N=CN=3)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 JGCVAIGYLJWSRQ-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
• QPDCJMXOIJUAPY-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-6-[1-(oxan-4-yl)butan-2-yl]-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=1C(CC)CC1CCOCC1 QPDCJMXOIJUAPY-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
• MXQVJLSQTSQARV-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-6-[1-(oxan-4-yl)butan-2-yl]-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=1C(CC)CC1CCOCC1 MXQVJLSQTSQARV-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
• 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
• 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 class 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 class 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
• JZXKPMBEMXENIN-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-[2-(1-ethylcyclohexa-2,4-dien-1-yl)ethyl]-4-hydroxy-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=1CCC1(CC)CC=CC=C1 JZXKPMBEMXENIN-UHFFFAOYSA-N 0.000 claims 1
• FJMYBVFUAYOJQU-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-[2-(1-ethylcyclohexa-2,4-dien-1-yl)ethyl]-4-hydroxy-2-oxopyran-3-yl]methyl]phenyl]-4-nitrobenzenesulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3C=CC(=CC=3)[N+]([O-])=O)C=CC=2)C(=O)OC=1CCC1(CC)CC=CC=C1 FJMYBVFUAYOJQU-UHFFFAOYSA-N 0.000 claims 1
• CQDFUTOTSQNYDA-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-[2-(1-ethylcyclohexa-2,4-dien-1-yl)ethyl]-4-hydroxy-2-oxopyran-3-yl]methyl]phenyl]-7h-purine-6-sulfonamide Chemical class 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=1CCC1(CC)CC=CC=C1 CQDFUTOTSQNYDA-UHFFFAOYSA-N 0.000 claims 1
• VCYFFEXWGWBGHJ-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-[2-(1-ethylcyclohexa-2,4-dien-1-yl)ethyl]-4-hydroxy-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=1CCC1(CC)CC=CC=C1 VCYFFEXWGWBGHJ-UHFFFAOYSA-N 0.000 claims 1
• DSQLQPDDPROGCM-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-[2-(1-ethylcyclohexa-2,4-dien-1-yl)ethyl]-4-hydroxy-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=1CCC1(CC)CC=CC=C1 DSQLQPDDPROGCM-UHFFFAOYSA-N 0.000 claims 1
• MTMYDOQCUYZZCS-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-[2-(1-ethylcyclohexa-2,4-dien-1-yl)ethyl]-4-hydroxy-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=1CCC1(CC)CC=CC=C1 MTMYDOQCUYZZCS-UHFFFAOYSA-N 0.000 claims 1
• BDFXHUHFRWHVHA-UHFFFAOYSA-N n-[3-[cyclopropyl-[6-[2-(1-ethylcyclohexa-2,4-dien-1-yl)ethyl]-4-hydroxy-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=1CCC1(CC)CC=CC=C1 BDFXHUHFRWHVHA-UHFFFAOYSA-N 0.000 claims 1
• JVPJFIJBUHEIOH-AZKKKJBWSA-N n-[3-[cyclopropyl-[6-[2-[(1r)-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=1CC[C@]1(CC)CC=CC=C1 JVPJFIJBUHEIOH-AZKKKJBWSA-N 0.000 claims 1
• 102100034343 Integrase Human genes 0.000 abstract description 29
• 108010092799 RNA-directed DNA polymerase Proteins 0.000 abstract description 29
• VXIXUWQIVKSKSA-UHFFFAOYSA-N 4-hydroxycoumarin Chemical compound C1=CC=CC2=C1OC(=O)C=C2O VXIXUWQIVKSKSA-UHFFFAOYSA-N 0.000 abstract description 17
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 9
• 230000002401 inhibitory effect Effects 0.000 abstract description 7
• QBDAFARLDLCWAT-UHFFFAOYSA-N 2,3-dihydropyran-6-one Chemical compound O=C1OCCC=C1 QBDAFARLDLCWAT-UHFFFAOYSA-N 0.000 abstract description 3
• 241000124008 Mammalia Species 0.000 abstract 1
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 420
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 229
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 222
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 192
• 238000002360 preparation method Methods 0.000 description 145
• 239000000243 solution Substances 0.000 description 109
• 238000005481 NMR spectroscopy Methods 0.000 description 106
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 103
• 230000000704 physical effect Effects 0.000 description 99
• 239000000203 mixture Substances 0.000 description 97
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 96
• 235000019439 ethyl acetate Nutrition 0.000 description 86
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 81
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 77
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 75
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
• 239000007787 solid Substances 0.000 description 51
• 230000008569 process Effects 0.000 description 50
• 230000002829 reductive effect Effects 0.000 description 48
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
• 239000000543 intermediate Substances 0.000 description 44
• 235000019441 ethanol Nutrition 0.000 description 43
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 42
• 239000000460 chlorine Substances 0.000 description 39
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 38
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 37
• 238000006243 chemical reaction Methods 0.000 description 37
• 208000030507 AIDS Diseases 0.000 description 36
• QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 34
• ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 34
• 239000002904 solvent Substances 0.000 description 34
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
• 239000000047 product Substances 0.000 description 32
• 241000700605 Viruses Species 0.000 description 31
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
• JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 28
• 238000003818 flash chromatography Methods 0.000 description 27
• 239000002585 base Substances 0.000 description 26
• 239000011541 reaction mixture Substances 0.000 description 26
• 230000006103 sulfonylation Effects 0.000 description 26
• 238000005694 sulfonylation reaction Methods 0.000 description 26
• XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 24
• 241000725303 Human immunodeficiency virus Species 0.000 description 24
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
• KXUGUWTUFUWYRS-UHFFFAOYSA-N 1-methylimidazole-4-sulfonyl chloride Chemical compound CN1C=NC(S(Cl)(=O)=O)=C1 KXUGUWTUFUWYRS-UHFFFAOYSA-N 0.000 description 23
• 238000010992 reflux Methods 0.000 description 23
• 239000003054 catalyst Substances 0.000 description 22
• 239000012044 organic layer Substances 0.000 description 22
• 239000002253 acid Substances 0.000 description 21
• 239000003112 inhibitor Substances 0.000 description 21
• 150000002576 ketones Chemical class 0.000 description 21
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 21
• 108091005804 Peptidases Proteins 0.000 description 20
• 102000035195 Peptidases Human genes 0.000 description 20
• 239000004365 Protease Substances 0.000 description 20
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
• 238000007792 addition Methods 0.000 description 20
• IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 20
• 239000010410 layer Substances 0.000 description 19
• OKIJSNGRQAOIGZ-UHFFFAOYSA-N Butopyronoxyl Chemical compound CCCCOC(=O)C1=CC(=O)CC(C)(C)O1 OKIJSNGRQAOIGZ-UHFFFAOYSA-N 0.000 description 18
• 102000004190 Enzymes Human genes 0.000 description 18
• 108090000790 Enzymes Proteins 0.000 description 18
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 18
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 18
• 238000002451 electron ionisation mass spectrometry Methods 0.000 description 18
• 229940088598 enzyme Drugs 0.000 description 18
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 18
• 235000019341 magnesium sulphate Nutrition 0.000 description 18
• 238000003786 synthesis reaction Methods 0.000 description 18
• NSYSSMYQPLSPOD-UHFFFAOYSA-N triacetate lactone Chemical compound CC1=CC(O)=CC(=O)O1 NSYSSMYQPLSPOD-UHFFFAOYSA-N 0.000 description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 17
• 125000004093 cyano group Chemical group *C#N 0.000 description 17
• QMMFVYPAHWMCMS-UHFFFAOYSA-N dimethylsulfide Substances CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 17
• 239000003921 oil Substances 0.000 description 17
• 235000019198 oils Nutrition 0.000 description 17
• 229910052739 hydrogen Inorganic materials 0.000 description 16
• 239000001257 hydrogen Substances 0.000 description 16
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
• 239000000741 silica gel Substances 0.000 description 16
• 229910002027 silica gel Inorganic materials 0.000 description 16
• 229960001866 silicon dioxide Drugs 0.000 description 16
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
• 239000000706 filtrate Substances 0.000 description 15
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 15
• 239000012267 brine Substances 0.000 description 14
• 238000000921 elemental analysis Methods 0.000 description 14
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
• HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 14
• AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 13
• 229960002555 zidovudine Drugs 0.000 description 13
• PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
• 108010010369 HIV Protease Proteins 0.000 description 12
• 229960000583 acetic acid Drugs 0.000 description 12
• 230000005764 inhibitory process Effects 0.000 description 12
• 150000002924 oxiranes Chemical class 0.000 description 12
• 239000000137 peptide hydrolase inhibitor Substances 0.000 description 12
• HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 12
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 12
• 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 11
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 11
• VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 11
• 150000001450 anions Chemical class 0.000 description 11
• 230000015572 biosynthetic process Effects 0.000 description 11
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
• 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
• 208000015181 infectious disease Diseases 0.000 description 11
• 229910052763 palladium Inorganic materials 0.000 description 11
• 235000019419 proteases Nutrition 0.000 description 11
• 230000010076 replication Effects 0.000 description 11
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
• 229910021589 Copper(I) bromide Inorganic materials 0.000 description 10
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
• VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
• 238000009903 catalytic hydrogenation reaction Methods 0.000 description 10
• ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 10
• 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 10
• 239000006260 foam Substances 0.000 description 10
• 238000005984 hydrogenation reaction Methods 0.000 description 10
• 239000002808 molecular sieve Substances 0.000 description 10
• URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 10
• 229940001593 sodium carbonate Drugs 0.000 description 10
• 229910000029 sodium carbonate Inorganic materials 0.000 description 10
• 150000003512 tertiary amines Chemical class 0.000 description 10
• 230000003612 virological effect Effects 0.000 description 10
• PJVWKTKQMONHTI-UHFFFAOYSA-N warfarin Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 PJVWKTKQMONHTI-UHFFFAOYSA-N 0.000 description 10
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
• 241000713772 Human immunodeficiency virus 1 Species 0.000 description 9
• 108010016183 Human immunodeficiency virus 1 p16 protease Proteins 0.000 description 9
• WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 9
• ZMXDDKWLCZADIW-UHFFFAOYSA-N Vilsmeier-Haack reagent Natural products CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 description 9
• 229910052799 carbon Inorganic materials 0.000 description 9
• 230000003197 catalytic effect Effects 0.000 description 9
• 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 9
• 239000000463 material Substances 0.000 description 9
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 9
• 238000003756 stirring Methods 0.000 description 9
• 229960005080 warfarin Drugs 0.000 description 9
• ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 8
• XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 8
• YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 8
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
• 108010017640 Aspartic Acid Proteases Proteins 0.000 description 8
• 102000004580 Aspartic Acid Proteases Human genes 0.000 description 8
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
• 125000003118 aryl group Chemical group 0.000 description 8
• 238000003556 assay Methods 0.000 description 8
• 230000027455 binding Effects 0.000 description 8
• 210000004027 cell Anatomy 0.000 description 8
• 239000003153 chemical reaction reagent Substances 0.000 description 8
• 238000004587 chromatography analysis Methods 0.000 description 8
• 150000004775 coumarins Chemical class 0.000 description 8
• 201000010099 disease Diseases 0.000 description 8
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
• 150000002148 esters Chemical class 0.000 description 8
• 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 8
• CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 8
• KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 8
• 229910000027 potassium carbonate Inorganic materials 0.000 description 8
• 238000011160 research Methods 0.000 description 8
• 229910052938 sodium sulfate Inorganic materials 0.000 description 8
• 235000011152 sodium sulphate Nutrition 0.000 description 8
• 239000000758 substrate Substances 0.000 description 8
• 239000000725 suspension Substances 0.000 description 8
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
• 150000001299 aldehydes Chemical class 0.000 description 7
• HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 7
• 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 7
• 238000004296 chiral HPLC Methods 0.000 description 7
• 230000000694 effects Effects 0.000 description 7
• 239000012467 final product Substances 0.000 description 7
• 239000004030 hiv protease inhibitor Substances 0.000 description 7
• 229910052751 metal Inorganic materials 0.000 description 7
• 239000002184 metal Substances 0.000 description 7
• 108090000765 processed proteins & peptides Proteins 0.000 description 7
• 102000004196 processed proteins & peptides Human genes 0.000 description 7
• BFXHJFKKRGVUMU-UHFFFAOYSA-N 4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1 BFXHJFKKRGVUMU-UHFFFAOYSA-N 0.000 description 6
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
• KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
• 206010035664 Pneumonia Diseases 0.000 description 6
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 6
• 239000012346 acetyl chloride Substances 0.000 description 6
• 125000000217 alkyl group Chemical group 0.000 description 6
• 239000003146 anticoagulant agent Substances 0.000 description 6
• 229940127219 anticoagulant drug Drugs 0.000 description 6
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
• 239000002775 capsule Substances 0.000 description 6
• 125000004432 carbon atom Chemical group C* 0.000 description 6
• 229910052801 chlorine Inorganic materials 0.000 description 6
• 238000003776 cleavage reaction Methods 0.000 description 6
• 238000004440 column chromatography Methods 0.000 description 6
• 229960000956 coumarin Drugs 0.000 description 6
• 125000000422 delta-lactone group Chemical group 0.000 description 6
• 229940043279 diisopropylamine Drugs 0.000 description 6
• 239000000539 dimer Substances 0.000 description 6
• 239000003814 drug Substances 0.000 description 6
• 239000000284 extract Substances 0.000 description 6
• 238000009472 formulation Methods 0.000 description 6
• 238000002347 injection Methods 0.000 description 6
• 239000007924 injection Substances 0.000 description 6
• NQBKFULMFQMZBE-UHFFFAOYSA-N n-bz-3-benzanthronylpyrazolanthron Chemical compound C12=CC=CC(C(=O)C=3C4=CC=CC=3)=C2C4=NN1C1=CC=C2C3=C1C1=CC=CC=C1C(=O)C3=CC=C2 NQBKFULMFQMZBE-UHFFFAOYSA-N 0.000 description 6
• 125000006239 protecting group Chemical group 0.000 description 6
• JUYUYCIJACTHMK-UHFFFAOYSA-N quinoline-8-sulfonyl chloride Chemical compound C1=CN=C2C(S(=O)(=O)Cl)=CC=CC2=C1 JUYUYCIJACTHMK-UHFFFAOYSA-N 0.000 description 6
• 230000007017 scission Effects 0.000 description 6
• 239000012279 sodium borohydride Substances 0.000 description 6
• 229910000033 sodium borohydride Inorganic materials 0.000 description 6
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 6
• RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
• 230000007704 transition Effects 0.000 description 6
• CFWJJSGESLDGKF-UHFFFAOYSA-N 2-methoxy-2-methyl-1,3-dioxolane Chemical compound COC1(C)OCCO1 CFWJJSGESLDGKF-UHFFFAOYSA-N 0.000 description 5
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 5
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
• JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• 241000282412 Homo Species 0.000 description 5
• 101000940871 Homo sapiens Endonuclease Proteins 0.000 description 5
• 101001066676 Homo sapiens Integrase Proteins 0.000 description 5
• 101001066681 Homo sapiens Integrase Proteins 0.000 description 5
• 101001066682 Homo sapiens Integrase Proteins 0.000 description 5
• 101001066686 Homo sapiens Integrase Proteins 0.000 description 5
• 101001066687 Homo sapiens Integrase Proteins 0.000 description 5
• 101001066688 Homo sapiens Integrase Proteins 0.000 description 5
• 101001066689 Homo sapiens Integrase Proteins 0.000 description 5
• 101001067009 Homo sapiens Integrase Proteins 0.000 description 5
• 101001066690 Homo sapiens Ribonuclease H Proteins 0.000 description 5
• GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
• HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
• 239000008346 aqueous phase Substances 0.000 description 5
• 239000011324 bead Substances 0.000 description 5
• UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 5
• 238000009833 condensation Methods 0.000 description 5
• 230000005494 condensation Effects 0.000 description 5
• 150000002085 enols Chemical class 0.000 description 5
• 239000012065 filter cake Substances 0.000 description 5
• 238000010438 heat treatment Methods 0.000 description 5
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
• 239000007788 liquid Substances 0.000 description 5
• YZOSYOXYACDPMN-UHFFFAOYSA-M magnesium;n,n-bis(trimethylsilyl)aniline;chloride Chemical compound [Mg+2].[Cl-].C[Si](C)(C)N([Si](C)(C)C)C1=CC=C[C-]=C1 YZOSYOXYACDPMN-UHFFFAOYSA-M 0.000 description 5
• 238000001819 mass spectrum Methods 0.000 description 5
• 150000004702 methyl esters Chemical class 0.000 description 5
• 239000002480 mineral oil Substances 0.000 description 5
• 235000010446 mineral oil Nutrition 0.000 description 5
• 239000012038 nucleophile Substances 0.000 description 5
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
• 229920001184 polypeptide Polymers 0.000 description 5
• 238000001953 recrystallisation Methods 0.000 description 5
• 239000007858 starting material Substances 0.000 description 5
• 238000003419 tautomerization reaction Methods 0.000 description 5
• 229910052725 zinc Inorganic materials 0.000 description 5
• 239000011701 zinc Substances 0.000 description 5
• CJXAGOKSVZAZAI-UHFFFAOYSA-N 1-(2-iodoethoxy)-2-methoxyethane Chemical compound COCCOCCI CJXAGOKSVZAZAI-UHFFFAOYSA-N 0.000 description 4
• FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 4
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 4
• SIXYIEWSUKAOEN-UHFFFAOYSA-N 3-aminobenzaldehyde Chemical compound NC1=CC=CC(C=O)=C1 SIXYIEWSUKAOEN-UHFFFAOYSA-N 0.000 description 4
• RLEGNEMAZOQPDY-UHFFFAOYSA-N 3-cyclooctylpyran-2-one Chemical compound O=C1OC=CC=C1C1CCCCCCC1 RLEGNEMAZOQPDY-UHFFFAOYSA-N 0.000 description 4
• PXNRZJNTMDCHFR-UHFFFAOYSA-N 4-hydroxy-2-methyl-2,3-dihydropyran-6-one Chemical compound CC1CC(O)=CC(=O)O1 PXNRZJNTMDCHFR-UHFFFAOYSA-N 0.000 description 4
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
• 239000007818 Grignard reagent Substances 0.000 description 4
• 208000031886 HIV Infections Diseases 0.000 description 4
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 4
• 229910052782 aluminium Inorganic materials 0.000 description 4
• XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
• 229910021529 ammonia Inorganic materials 0.000 description 4
• 235000019270 ammonium chloride Nutrition 0.000 description 4
• 230000000840 anti-viral effect Effects 0.000 description 4
• 239000011260 aqueous acid Substances 0.000 description 4
• 239000012300 argon atmosphere Substances 0.000 description 4
• 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
• 229910052794 bromium Inorganic materials 0.000 description 4
• 150000001721 carbon Chemical group 0.000 description 4
• 235000001671 coumarin Nutrition 0.000 description 4
• HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
• SPBSPZKRZGRRSE-UHFFFAOYSA-N cyclopropyl-(3-nitrophenyl)methanone Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)C2CC2)=C1 SPBSPZKRZGRRSE-UHFFFAOYSA-N 0.000 description 4
• 238000001914 filtration Methods 0.000 description 4
• 238000007429 general method Methods 0.000 description 4
• 150000004795 grignard reagents Chemical class 0.000 description 4
• GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 4
• 238000011065 in-situ storage Methods 0.000 description 4
• 230000002458 infectious effect Effects 0.000 description 4
• 229910052744 lithium Inorganic materials 0.000 description 4
• CQRPUKWAZPZXTO-UHFFFAOYSA-M magnesium;2-methylpropane;chloride Chemical compound [Mg+2].[Cl-].C[C-](C)C CQRPUKWAZPZXTO-UHFFFAOYSA-M 0.000 description 4
• 238000004519 manufacturing process Methods 0.000 description 4
• VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
• UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 4
• 235000018102 proteins Nutrition 0.000 description 4
• 108090000623 proteins and genes Proteins 0.000 description 4
• 102000004169 proteins and genes Human genes 0.000 description 4
• 125000001424 substituent group Chemical group 0.000 description 4
• 238000006467 substitution reaction Methods 0.000 description 4
• 150000003573 thiols Chemical class 0.000 description 4
• PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 4
• 239000003981 vehicle Substances 0.000 description 4
• QDMNNMIOWVJVLY-QMMMGPOBSA-N (4r)-4-phenyl-1,3-oxazolidin-2-one Chemical compound C1OC(=O)N[C@@H]1C1=CC=CC=C1 QDMNNMIOWVJVLY-QMMMGPOBSA-N 0.000 description 3
• MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 3
• LTSLTKRXEXDPIW-UHFFFAOYSA-N 2-methoxy-2-methyl-1,3-dioxole Chemical compound COC1(C)OC=CO1 LTSLTKRXEXDPIW-UHFFFAOYSA-N 0.000 description 3
• LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 3
• WJKOLHDGHRXNEX-UHFFFAOYSA-N 4,8-diphenylundecan-6-one Chemical compound C(CC)C(CC(=O)CC(CCC)C1=CC=CC=C1)C1=CC=CC=C1 WJKOLHDGHRXNEX-UHFFFAOYSA-N 0.000 description 3
• DBMFYTQPPBBKHI-UHFFFAOYSA-N 4-cyanobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(C#N)C=C1 DBMFYTQPPBBKHI-UHFFFAOYSA-N 0.000 description 3
• VEBNLAJYXDESLD-UHFFFAOYSA-N 4-hydroxy-3-(1-phenylbutyl)chromen-2-one Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CCC)C1=CC=CC=C1 VEBNLAJYXDESLD-UHFFFAOYSA-N 0.000 description 3
• HGHYHEXRSFIVOQ-UHFFFAOYSA-N 4-hydroxy-3-(3-phenoxypropyl)chromen-2-one Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1CCCOC1=CC=CC=C1 HGHYHEXRSFIVOQ-UHFFFAOYSA-N 0.000 description 3
• NQIBZRCQXREWIP-UHFFFAOYSA-N 4-hydroxycycloocta[b]pyran-2-one Chemical compound C1=CC=CC=CC2=C1OC(=O)C=C2O NQIBZRCQXREWIP-UHFFFAOYSA-N 0.000 description 3
• VNZOLPIHDIJPBZ-UHFFFAOYSA-N 4-hydroxypyran-2-one Chemical compound OC=1C=COC(=O)C=1 VNZOLPIHDIJPBZ-UHFFFAOYSA-N 0.000 description 3
• NPQKQKITPJTEBK-UHFFFAOYSA-N 6-butan-2-yl-3-ethyl-4-hydroxypyran-2-one Chemical compound CCC(C)C1=CC(O)=C(CC)C(=O)O1 NPQKQKITPJTEBK-UHFFFAOYSA-N 0.000 description 3
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
• KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 3
• BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
• KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
• YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 3
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
• 229940122440 HIV protease inhibitor Drugs 0.000 description 3
• WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
• 239000004472 Lysine Substances 0.000 description 3
• KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 3
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
• 235000019502 Orange oil Nutrition 0.000 description 3
• 229940124158 Protease/peptidase inhibitor Drugs 0.000 description 3
• 108010090804 Streptavidin Proteins 0.000 description 3
• 150000001336 alkenes Chemical class 0.000 description 3
• 238000005804 alkylation reaction Methods 0.000 description 3
• 230000036436 anti-hiv Effects 0.000 description 3
• ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 3
• 125000000637 arginyl group Chemical class N[C@@H](CCCNC(N)=N)C(=O)* 0.000 description 3
• 229910052786 argon Inorganic materials 0.000 description 3
• 230000037396 body weight Effects 0.000 description 3
• 229910000085 borane Inorganic materials 0.000 description 3
• RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 3
• OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 3
• IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 3
• 238000004891 communication Methods 0.000 description 3
• 238000001816 cooling Methods 0.000 description 3
• DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 description 3
• PJRHFTYXYCVOSJ-UHFFFAOYSA-N cyclopropyl(phenyl)methanone Chemical compound C=1C=CC=CC=1C(=O)C1CC1 PJRHFTYXYCVOSJ-UHFFFAOYSA-N 0.000 description 3
• GUDMZGLFZNLYEY-UHFFFAOYSA-N cyclopropylmethanol Chemical compound OCC1CC1 GUDMZGLFZNLYEY-UHFFFAOYSA-N 0.000 description 3
• 238000013461 design Methods 0.000 description 3
• 229910052805 deuterium Inorganic materials 0.000 description 3
• 229940079593 drug Drugs 0.000 description 3
• OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical class CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
• 125000001072 heteroaryl group Chemical group 0.000 description 3
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
• 125000000468 ketone group Chemical group 0.000 description 3
• 230000002147 killing effect Effects 0.000 description 3
• AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 3
• KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 3
• UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 3
• 210000004698 lymphocyte Anatomy 0.000 description 3
• FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 3
• RYEXTBOQKFUPOE-UHFFFAOYSA-M magnesium;propane;chloride Chemical compound [Mg+2].[Cl-].CC[CH2-] RYEXTBOQKFUPOE-UHFFFAOYSA-M 0.000 description 3
• 230000001404 mediated effect Effects 0.000 description 3
• DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 3
• KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 3
• 230000014508 negative regulation of coagulation Effects 0.000 description 3
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
• JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
• 239000010502 orange oil Substances 0.000 description 3
• 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 3
• QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
• 210000005259 peripheral blood Anatomy 0.000 description 3
• 239000011886 peripheral blood Substances 0.000 description 3
• PWXJULSLLONQHY-UHFFFAOYSA-N phenylcarbamic acid Chemical compound OC(=O)NC1=CC=CC=C1 PWXJULSLLONQHY-UHFFFAOYSA-N 0.000 description 3
• 239000008363 phosphate buffer Substances 0.000 description 3
• RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 description 3
• NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
• 238000010791 quenching Methods 0.000 description 3
• 230000000171 quenching effect Effects 0.000 description 3
• 238000012216 screening Methods 0.000 description 3
• 230000035945 sensitivity Effects 0.000 description 3
• 238000000926 separation method Methods 0.000 description 3
• 235000017557 sodium bicarbonate Nutrition 0.000 description 3
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
• 239000011780 sodium chloride Substances 0.000 description 3
• FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
• 159000000000 sodium salts Chemical class 0.000 description 3
• 238000010561 standard procedure Methods 0.000 description 3
• 239000000126 substance Substances 0.000 description 3
• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 3
• XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 3
• 230000001988 toxicity Effects 0.000 description 3
• 231100000419 toxicity Toxicity 0.000 description 3
• VOITXYVAKOUIBA-UHFFFAOYSA-N triethylaluminium Chemical compound CC[Al](CC)CC VOITXYVAKOUIBA-UHFFFAOYSA-N 0.000 description 3
• DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
• FSWNRRSWFBXQCL-UHFFFAOYSA-N (3-bromophenyl)methanol Chemical compound OCC1=CC=CC(Br)=C1 FSWNRRSWFBXQCL-UHFFFAOYSA-N 0.000 description 2
• OJOFMLDBXPDXLQ-SECBINFHSA-N (4r)-4-benzyl-1,3-oxazolidin-2-one Chemical compound C1OC(=O)N[C@@H]1CC1=CC=CC=C1 OJOFMLDBXPDXLQ-SECBINFHSA-N 0.000 description 2
• OJOFMLDBXPDXLQ-VIFPVBQESA-N (4s)-4-benzyl-1,3-oxazolidin-2-one Chemical compound C1OC(=O)N[C@H]1CC1=CC=CC=C1 OJOFMLDBXPDXLQ-VIFPVBQESA-N 0.000 description 2
• QDMNNMIOWVJVLY-MRVPVSSYSA-N (4s)-4-phenyl-1,3-oxazolidin-2-one Chemical compound C1OC(=O)N[C@H]1C1=CC=CC=C1 QDMNNMIOWVJVLY-MRVPVSSYSA-N 0.000 description 2
• BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 2
• NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
• GCFPFWRHYINTRX-UHFFFAOYSA-M 2-hydroxy-4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C(O)=C1 GCFPFWRHYINTRX-UHFFFAOYSA-M 0.000 description 2
• BYDRTKVGBRTTIT-UHFFFAOYSA-N 2-methylprop-2-en-1-ol Chemical compound CC(=C)CO BYDRTKVGBRTTIT-UHFFFAOYSA-N 0.000 description 2
• HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
• ZPNYHQZRGWFLST-UHFFFAOYSA-N 4'-Hydroxy-phenprocoumon Natural products OC=1C2=CC=CC=C2OC(=O)C=1C(CC)C1=CC=C(O)C=C1 ZPNYHQZRGWFLST-UHFFFAOYSA-N 0.000 description 2
• SZNMHLAVPHXYCC-UHFFFAOYSA-N 4-hydroxy-2,2,5-trimethyl-3h-pyran-6-one Chemical compound CC1=C(O)CC(C)(C)OC1=O SZNMHLAVPHXYCC-UHFFFAOYSA-N 0.000 description 2
• MXEJFXRULRDYHS-UHFFFAOYSA-N 4-hydroxy-2,5-dimethyl-2,3-dihydropyran-6-one Chemical compound CC1CC(O)=C(C)C(=O)O1 MXEJFXRULRDYHS-UHFFFAOYSA-N 0.000 description 2
• ZCQSVTPIFUGZOW-UHFFFAOYSA-N 4-hydroxy-3-(1-phenylethyl)chromen-2-one Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(C)C1=CC=CC=C1 ZCQSVTPIFUGZOW-UHFFFAOYSA-N 0.000 description 2
• SGOOQMRIPALTEL-UHFFFAOYSA-N 4-hydroxy-N,1-dimethyl-2-oxo-N-phenyl-3-quinolinecarboxamide Chemical compound OC=1C2=CC=CC=C2N(C)C(=O)C=1C(=O)N(C)C1=CC=CC=C1 SGOOQMRIPALTEL-UHFFFAOYSA-N 0.000 description 2
• MRIFFPWOMKLYKZ-UHFFFAOYSA-N 5-(trifluoromethyl)pyridine-2-sulfonyl chloride Chemical compound FC(F)(F)C1=CC=C(S(Cl)(=O)=O)N=C1 MRIFFPWOMKLYKZ-UHFFFAOYSA-N 0.000 description 2
• XUXSGYYVYLYBFR-UHFFFAOYSA-N 5-cyanopyridine-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(C#N)C=N1 XUXSGYYVYLYBFR-UHFFFAOYSA-N 0.000 description 2
• CQBHSRLUQDYPBU-UHFFFAOYSA-N 5-hydroxy-9,10-dioxoanthracene-1-sulfonamide Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C=CC=C2S(=O)(=O)N CQBHSRLUQDYPBU-UHFFFAOYSA-N 0.000 description 2
• BKRXPRMCBOAGQH-UHFFFAOYSA-N 6-Hydroxyphenprocoumon Natural products OC=1C2=CC(O)=CC=C2OC(=O)C=1C(CC)C1=CC=CC=C1 BKRXPRMCBOAGQH-UHFFFAOYSA-N 0.000 description 2
• HBAPGROFUGJSGR-UHFFFAOYSA-N 7-Hydroxyphenprocoumon Natural products OC=1C2=CC=C(O)C=C2OC(=O)C=1C(CC)C1=CC=CC=C1 HBAPGROFUGJSGR-UHFFFAOYSA-N 0.000 description 2
• CJIJXIFQYOPWTF-UHFFFAOYSA-N 7-hydroxycoumarin Natural products O1C(=O)C=CC2=CC(O)=CC=C21 CJIJXIFQYOPWTF-UHFFFAOYSA-N 0.000 description 2
• 244000215068 Acacia senegal Species 0.000 description 2
• 206010003581 Asymptomatic HIV infection Diseases 0.000 description 2
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
• LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
• 239000002126 C01EB10 - Adenosine Substances 0.000 description 2
• 241000222122 Candida albicans Species 0.000 description 2
• 206010007134 Candida infections Diseases 0.000 description 2
• 239000004215 Carbon black (E152) Substances 0.000 description 2
• XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
• 241000282326 Felis catus Species 0.000 description 2
• 229920000084 Gum arabic Polymers 0.000 description 2
• 201000002563 Histoplasmosis Diseases 0.000 description 2
• 241000714260 Human T-lymphotropic virus 1 Species 0.000 description 2
• 241000714259 Human T-lymphotropic virus 2 Species 0.000 description 2
• MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
• 208000007766 Kaposi sarcoma Diseases 0.000 description 2
• KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 2
• FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
• 206010028980 Neoplasm Diseases 0.000 description 2
• 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 2
• 101000642811 Oryza sativa subsp. indica Soluble starch synthase 1, chloroplastic/amyloplastic Proteins 0.000 description 2
• CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 2
• 239000002202 Polyethylene glycol Substances 0.000 description 2
• 239000004793 Polystyrene Substances 0.000 description 2
• VOLMSPGWNYJHQQ-UHFFFAOYSA-N Pyranone Natural products CC1=C(O)C(=O)C(O)CO1 VOLMSPGWNYJHQQ-UHFFFAOYSA-N 0.000 description 2
• UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
• 238000006859 Swern oxidation reaction Methods 0.000 description 2
• 208000000389 T-cell leukemia Diseases 0.000 description 2
• 208000028530 T-cell lymphoblastic leukemia/lymphoma Diseases 0.000 description 2
• 210000001744 T-lymphocyte Anatomy 0.000 description 2
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
• RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
• 108700022715 Viral Proteases Proteins 0.000 description 2
• 239000000205 acacia gum Substances 0.000 description 2
• 235000010489 acacia gum Nutrition 0.000 description 2
• 150000007513 acids Chemical class 0.000 description 2
• 229960005305 adenosine Drugs 0.000 description 2
• 239000002671 adjuvant Substances 0.000 description 2
• 150000001298 alcohols Chemical class 0.000 description 2
• 230000029936 alkylation Effects 0.000 description 2
• MJWPFSQVORELDX-UHFFFAOYSA-K aluminium formate Chemical compound [Al+3].[O-]C=O.[O-]C=O.[O-]C=O MJWPFSQVORELDX-UHFFFAOYSA-K 0.000 description 2
• 235000001014 amino acid Nutrition 0.000 description 2
• 150000001413 amino acids Chemical class 0.000 description 2
• 230000000844 anti-bacterial effect Effects 0.000 description 2
• 230000000845 anti-microbial effect Effects 0.000 description 2
• 239000000427 antigen Substances 0.000 description 2
• 108091007433 antigens Proteins 0.000 description 2
• 102000036639 antigens Human genes 0.000 description 2
• 239000003443 antiviral agent Substances 0.000 description 2
• 239000008135 aqueous vehicle Substances 0.000 description 2
• 238000011914 asymmetric synthesis Methods 0.000 description 2
• 239000012298 atmosphere Substances 0.000 description 2
• CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 2
• 235000019445 benzyl alcohol Nutrition 0.000 description 2
• 210000004369 blood Anatomy 0.000 description 2
• 239000008280 blood Substances 0.000 description 2
• ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 2
• AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 2
• 244000309464 bull Species 0.000 description 2
• 159000000007 calcium salts Chemical class 0.000 description 2
• 201000003984 candidiasis Diseases 0.000 description 2
• 210000000234 capsid Anatomy 0.000 description 2
• UWCHSDIUMBNDLT-UHFFFAOYSA-L copper;methylsulfanylmethane;dibromide Chemical compound CSC.Br[Cu]Br UWCHSDIUMBNDLT-UHFFFAOYSA-L 0.000 description 2
• 239000013078 crystal Substances 0.000 description 2
• JMYVMOUINOAAPA-UHFFFAOYSA-N cyclopropanecarbaldehyde Chemical compound O=CC1CC1 JMYVMOUINOAAPA-UHFFFAOYSA-N 0.000 description 2
• 150000008380 cyclopropylphenylketones Chemical class 0.000 description 2
• 238000000354 decomposition reaction Methods 0.000 description 2
• 238000010511 deprotection reaction Methods 0.000 description 2
• 230000005595 deprotonation Effects 0.000 description 2
• 238000010537 deprotonation reaction Methods 0.000 description 2
• BIPUHAHGLJKIPK-UHFFFAOYSA-N dicyclopropylmethanone Chemical compound C1CC1C(=O)C1CC1 BIPUHAHGLJKIPK-UHFFFAOYSA-N 0.000 description 2
• 150000002009 diols Chemical class 0.000 description 2
• 238000005516 engineering process Methods 0.000 description 2
• FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 2
• NUVBSKCKDOMJSU-UHFFFAOYSA-N ethylparaben Chemical compound CCOC(=O)C1=CC=C(O)C=C1 NUVBSKCKDOMJSU-UHFFFAOYSA-N 0.000 description 2
• 239000000796 flavoring agent Substances 0.000 description 2
• 125000000524 functional group Chemical group 0.000 description 2
• 230000004927 fusion Effects 0.000 description 2
• 239000007789 gas Substances 0.000 description 2
• 125000005843 halogen group Chemical group 0.000 description 2
• 150000002390 heteroarenes Chemical class 0.000 description 2
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 description 2
• 210000005260 human cell Anatomy 0.000 description 2
• 229930195733 hydrocarbon Natural products 0.000 description 2
• 150000002430 hydrocarbons Chemical class 0.000 description 2
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
• NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
• 238000001990 intravenous administration Methods 0.000 description 2
• 150000002596 lactones Chemical class 0.000 description 2
• 239000003446 ligand Substances 0.000 description 2
• 239000012280 lithium aluminium hydride Substances 0.000 description 2
• 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 2
• 239000011777 magnesium Substances 0.000 description 2
• 229910052749 magnesium Inorganic materials 0.000 description 2
• HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
• YCCXQARVHOPWFJ-UHFFFAOYSA-M magnesium;ethane;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C YCCXQARVHOPWFJ-UHFFFAOYSA-M 0.000 description 2
• 230000014759 maintenance of location Effects 0.000 description 2
• NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
• 238000004949 mass spectrometry Methods 0.000 description 2
• 230000035800 maturation Effects 0.000 description 2
• 230000007246 mechanism Effects 0.000 description 2
• 229920000609 methyl cellulose Polymers 0.000 description 2
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
• 239000001923 methylcellulose Substances 0.000 description 2
• 235000010981 methylcellulose Nutrition 0.000 description 2
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
• 238000002156 mixing Methods 0.000 description 2
• 239000012452 mother liquor Substances 0.000 description 2
• 230000035772 mutation Effects 0.000 description 2
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
• 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
• PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 2
• 229910017604 nitric acid Inorganic materials 0.000 description 2
• 239000002777 nucleoside Substances 0.000 description 2
• 125000003835 nucleoside group Chemical group 0.000 description 2
• AVPKHOTUOHDTLW-UHFFFAOYSA-N oxane-4-carboxylic acid Chemical compound OC(=O)C1CCOCC1 AVPKHOTUOHDTLW-UHFFFAOYSA-N 0.000 description 2
• 230000003647 oxidation Effects 0.000 description 2
• 238000007254 oxidation reaction Methods 0.000 description 2
• 239000002245 particle Substances 0.000 description 2
• 210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 2
• 208000033808 peripheral neuropathy Diseases 0.000 description 2
• 239000008024 pharmaceutical diluent Substances 0.000 description 2
• 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
• 229910052697 platinum Inorganic materials 0.000 description 2
• 229920001223 polyethylene glycol Polymers 0.000 description 2
• 229920000642 polymer Polymers 0.000 description 2
• 229920002223 polystyrene Polymers 0.000 description 2
• 239000002243 precursor Substances 0.000 description 2
• DNAJDTIOMGISDS-UHFFFAOYSA-N prop-2-enylsilane Chemical compound [SiH3]CC=C DNAJDTIOMGISDS-UHFFFAOYSA-N 0.000 description 2
• SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 2
• 230000002685 pulmonary effect Effects 0.000 description 2
• LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 2
• 230000009467 reduction Effects 0.000 description 2
• 239000000523 sample Substances 0.000 description 2
• 210000002966 serum Anatomy 0.000 description 2
• XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 2
• 238000001694 spray drying Methods 0.000 description 2
• 230000000707 stereoselective effect Effects 0.000 description 2
• 239000011550 stock solution Substances 0.000 description 2
• 235000000346 sugar Nutrition 0.000 description 2
• 150000008163 sugars Chemical class 0.000 description 2
• 208000024891 symptom Diseases 0.000 description 2
• 150000003509 tertiary alcohols Chemical class 0.000 description 2
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
• 230000001225 therapeutic effect Effects 0.000 description 2
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
• 239000010936 titanium Substances 0.000 description 2
• 229910052719 titanium Inorganic materials 0.000 description 2
• 125000005270 trialkylamine group Chemical group 0.000 description 2
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
• JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical compound OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 2
• 239000001226 triphosphate Substances 0.000 description 2
• 235000011178 triphosphate Nutrition 0.000 description 2
• UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 2
• ORHBXUUXSCNDEV-UHFFFAOYSA-N umbelliferone Chemical compound C1=CC(=O)OC2=CC(O)=CC=C21 ORHBXUUXSCNDEV-UHFFFAOYSA-N 0.000 description 2
• 230000029812 viral genome replication Effects 0.000 description 2
• KIZNQHOVHYLYHY-UHFFFAOYSA-M zinc;prop-1-ene;bromide Chemical compound [Zn+2].[Br-].[CH2-]C=C KIZNQHOVHYLYHY-UHFFFAOYSA-M 0.000 description 2
• XGXPWPIVYFOKIH-UHFFFAOYSA-N (2,5-dimethyl-6-oxo-2,3-dihydropyran-4-yl) acetate Chemical compound CC1CC(OC(C)=O)=C(C)C(=O)O1 XGXPWPIVYFOKIH-UHFFFAOYSA-N 0.000 description 1
• XYUHPPVEDOOPDE-ZIAGYGMSSA-N (2R,5R)-2,5-diamino-2,5-bis(4-aminobutyl)hexanedioic acid Chemical class NCCCC[C@@](N)(CC[C@](N)(CCCCN)C(O)=O)C(O)=O XYUHPPVEDOOPDE-ZIAGYGMSSA-N 0.000 description 1
• PPFDHHLTYPCZQS-UHFFFAOYSA-N (3-aminophenyl)-cyclopropylmethanone Chemical compound NC1=CC=CC(C(=O)C2CC2)=C1 PPFDHHLTYPCZQS-UHFFFAOYSA-N 0.000 description 1
• WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
• VSPOTMOYDHRALZ-UHFFFAOYSA-N 1-(3-nitrophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=CC([N+]([O-])=O)=C1 VSPOTMOYDHRALZ-UHFFFAOYSA-N 0.000 description 1
• PJUPKRYGDFTMTM-UHFFFAOYSA-N 1-hydroxybenzotriazole;hydrate Chemical group O.C1=CC=C2N(O)N=NC2=C1 PJUPKRYGDFTMTM-UHFFFAOYSA-N 0.000 description 1
• NCIMAYPZWJQYGN-UHFFFAOYSA-N 1-methoxy-n,n,n',n'-tetramethylmethanediamine Chemical compound COC(N(C)C)N(C)C NCIMAYPZWJQYGN-UHFFFAOYSA-N 0.000 description 1
• KSZCAGWHZCZJLZ-UHFFFAOYSA-N 1-methylimidazole-4-sulfonic acid Chemical compound CN1C=NC(S(O)(=O)=O)=C1 KSZCAGWHZCZJLZ-UHFFFAOYSA-N 0.000 description 1
• GNXHCJXHOUPAJY-UHFFFAOYSA-N 11-oxatetracyclo[7.6.1.05,16.010,15]hexadeca-1,3,5(16),6,8,10(15),13-heptaen-12-one Chemical compound C1=CC(C=2C=CC(OC=22)=O)=C3C2=CC=CC3=C1 GNXHCJXHOUPAJY-UHFFFAOYSA-N 0.000 description 1
• 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
• HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 description 1
• PBCQXKZFPXBUSL-UHFFFAOYSA-N 2-(2-oxochromen-4-yl)acetic acid Chemical compound C1=CC=CC2=C1OC(=O)C=C2CC(=O)O PBCQXKZFPXBUSL-UHFFFAOYSA-N 0.000 description 1
• SGTNSNPWRIOYBX-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-{[2-(3,4-dimethoxyphenyl)ethyl](methyl)amino}-2-(propan-2-yl)pentanenitrile Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC(C#N)(C(C)C)C1=CC=C(OC)C(OC)=C1 SGTNSNPWRIOYBX-UHFFFAOYSA-N 0.000 description 1
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical group O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
• 125000005999 2-bromoethyl group Chemical group 0.000 description 1
• BAZVFQBTJPBRTJ-UHFFFAOYSA-N 2-chloro-5-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C(Cl)N=C1 BAZVFQBTJPBRTJ-UHFFFAOYSA-N 0.000 description 1
• YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
• ANGGPYSFTXVERY-UHFFFAOYSA-N 2-iodo-2-methylpropane Chemical compound CC(C)(C)I ANGGPYSFTXVERY-UHFFFAOYSA-N 0.000 description 1
• AOYOBWSGCQMROU-UHFFFAOYSA-N 2-sulfanylbenzonitrile Chemical compound SC1=CC=CC=C1C#N AOYOBWSGCQMROU-UHFFFAOYSA-N 0.000 description 1
• UMZCLZPXPCNKML-UHFFFAOYSA-N 2h-imidazo[4,5-d][1,3]thiazole Chemical compound C1=NC2=NCSC2=N1 UMZCLZPXPCNKML-UHFFFAOYSA-N 0.000 description 1
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
• RQKMHMADILDMKY-UHFFFAOYSA-N 3-(1,3-diphenylpropyl)-4-hydroxychromen-2-one Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C(C=1C=CC=CC=1)CCC1=CC=CC=C1 RQKMHMADILDMKY-UHFFFAOYSA-N 0.000 description 1
• SWYGZTLXAWFSAT-UHFFFAOYSA-N 3-(1-chloroprop-1-en-2-yl)-4-hydroxy-5-methyl-2,3-dihydropyran-6-one Chemical compound ClC=C(C)C1C(=C(C(OC1)=O)C)O SWYGZTLXAWFSAT-UHFFFAOYSA-N 0.000 description 1
• OISKRLKGIUAGLH-UHFFFAOYSA-N 3-(2,3-dihydro-1h-inden-1-yl)-4-hydroxychromen-2-one Chemical class C1=CC=CC2=C1OC(=O)C(C1C3=CC=CC=C3CC1)=C2O OISKRLKGIUAGLH-UHFFFAOYSA-N 0.000 description 1
• ORIBWNWUGUWUKV-UHFFFAOYSA-N 3-(3-nitrophenyl)prop-2-enoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C=CC(Cl)=O)=C1 ORIBWNWUGUWUKV-UHFFFAOYSA-N 0.000 description 1
• ZMKXWDPUXLPHCA-UHFFFAOYSA-N 3-(4-fluorophenyl)propanoic acid Chemical compound OC(=O)CCC1=CC=C(F)C=C1 ZMKXWDPUXLPHCA-UHFFFAOYSA-N 0.000 description 1
• UZWQQIFQWBHYBV-UHFFFAOYSA-N 3-(9h-benzo[7]annulen-6-yl)prop-2-enoic acid Chemical compound C1C=CC(C=CC(=O)O)=CC2=CC=CC=C21 UZWQQIFQWBHYBV-UHFFFAOYSA-N 0.000 description 1
• LBVZCSKDTGDAQW-UHFFFAOYSA-N 3-[(2-oxo-1,3-oxazolidin-3-yl)phosphanyl]-1,3-oxazolidin-2-one;hydrochloride Chemical compound [Cl-].O=C1OCCN1[PH2+]N1C(=O)OCC1 LBVZCSKDTGDAQW-UHFFFAOYSA-N 0.000 description 1
• LJONWUYBRVNZOA-UHFFFAOYSA-N 3-[(3-aminophenyl)-cyclopropylmethyl]-4-hydroxy-6-(1-hydroxypentan-3-yl)pyran-2-one Chemical compound O=C1OC(C(CCO)CC)=CC(O)=C1C(C=1C=C(N)C=CC=1)C1CC1 LJONWUYBRVNZOA-UHFFFAOYSA-N 0.000 description 1
• FOQQHKXJYIUOGX-UHFFFAOYSA-N 3-[(3-aminophenyl)-cyclopropylmethyl]-4-hydroxy-6-[1-(2-methoxyethoxy)pentan-3-yl]pyran-2-one Chemical compound O=C1OC(C(CCOCCOC)CC)=CC(O)=C1C(C=1C=C(N)C=CC=1)C1CC1 FOQQHKXJYIUOGX-UHFFFAOYSA-N 0.000 description 1
• ILWPQQWJLRWICA-UHFFFAOYSA-N 3-[(3-aminophenyl)-cyclopropylmethyl]-4-hydroxy-6-[3-(2-methoxyethoxy)propyl]pyran-2-one Chemical compound O=C1OC(CCCOCCOC)=CC(O)=C1C(C=1C=C(N)C=CC=1)C1CC1 ILWPQQWJLRWICA-UHFFFAOYSA-N 0.000 description 1
• DKJOJGOBANHEKJ-UHFFFAOYSA-N 3-[(3-aminophenyl)-cyclopropylmethyl]-6-(1,3-dicyclopropylpropan-2-yl)-4-hydroxypyran-2-one Chemical compound NC1=CC=CC(C(C2CC2)C=2C(OC(=CC=2O)C(CC2CC2)CC2CC2)=O)=C1 DKJOJGOBANHEKJ-UHFFFAOYSA-N 0.000 description 1
• NCFKTJZCSPKCMV-UHFFFAOYSA-N 3-[(4-chlorophenyl)-piperidin-1-ylmethyl]-4-hydroxy-6-methylpyran-2-one Chemical compound O=C1OC(C)=CC(O)=C1C(C=1C=CC(Cl)=CC=1)N1CCCCC1 NCFKTJZCSPKCMV-UHFFFAOYSA-N 0.000 description 1
• AVPDSASPSPWYQN-UHFFFAOYSA-N 3-[1-(4-chlorophenyl)-3-(4-nitrophenyl)prop-2-enyl]-4-hydroxy-6-methylpyran-2-one Chemical compound O=C1OC(C)=CC(O)=C1C(C=1C=CC(Cl)=CC=1)C=CC1=CC=C([N+]([O-])=O)C=C1 AVPDSASPSPWYQN-UHFFFAOYSA-N 0.000 description 1
• MEDWQIOGEUYFJU-UHFFFAOYSA-N 3-[1-(4-chlorophenyl)propyl]-4-hydroxy-6-methylpyran-2-one Chemical compound OC=1C=C(C)OC(=O)C=1C(CC)C1=CC=C(Cl)C=C1 MEDWQIOGEUYFJU-UHFFFAOYSA-N 0.000 description 1
• QGCOFSZSZWRICF-UHFFFAOYSA-N 3-[1-(4-chlorophenyl)propyl]-4-hydroxychromen-2-one Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC)C1=CC=C(Cl)C=C1 QGCOFSZSZWRICF-UHFFFAOYSA-N 0.000 description 1
• PKDMQIGCOKVYKA-UHFFFAOYSA-N 3-[1-(4-fluorophenyl)propyl]-4-hydroxychromen-2-one Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC)C1=CC=C(F)C=C1 PKDMQIGCOKVYKA-UHFFFAOYSA-N 0.000 description 1
• GZKPNTWVHFNCQJ-UHFFFAOYSA-N 3-[3-(4-chlorophenyl)-1-(4-nitrophenyl)prop-2-enyl]-4-hydroxy-6-methylpyran-2-one Chemical compound O=C1OC(C)=CC(O)=C1C(C=1C=CC(=CC=1)[N+]([O-])=O)C=CC1=CC=C(Cl)C=C1 GZKPNTWVHFNCQJ-UHFFFAOYSA-N 0.000 description 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 description 1
• 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 description 1
• CDDDJHDAZCRDQG-UHFFFAOYSA-N 3-[[3-(bromomethyl)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(CBr)C=CC=1)C1CC1 CDDDJHDAZCRDQG-UHFFFAOYSA-N 0.000 description 1
• QFFNZYAEZUJRDZ-UHFFFAOYSA-N 3-[[3-(chloromethyl)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(CCl)C=CC=1)C1CC1 QFFNZYAEZUJRDZ-UHFFFAOYSA-N 0.000 description 1
• PKDFFOWIBWGOHI-UHFFFAOYSA-N 3-[cyclohexyl(phenyl)methyl]-4-hydroxychromen-2-one Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C(C=1C=CC=CC=1)C1CCCCC1 PKDFFOWIBWGOHI-UHFFFAOYSA-N 0.000 description 1
• JZZGAYVXZRDQDC-UHFFFAOYSA-N 3-[cyclopropyl-[3-(hydroxymethyl)phenyl]methyl]-4-hydroxy-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-2-one Chemical compound OCC1=CC=CC(C(C2CC2)C=2C(OC=3CCCCCCC=3C=2O)=O)=C1 JZZGAYVXZRDQDC-UHFFFAOYSA-N 0.000 description 1
• PJQYZOKBNIAZTD-UHFFFAOYSA-N 3-[cyclopropyl-[3-(pyridin-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=CC=2)C=CC=1)C1CC1 PJQYZOKBNIAZTD-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• 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 description 1
• MFVISHUDZNKYFS-UHFFFAOYSA-N 3-[cyclopropyl-[3-(quinolin-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=C3C=CC=CC3=CC=2)C=CC=1)C1CC1 MFVISHUDZNKYFS-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• 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 description 1
• BBCYXBCXEQADSJ-UHFFFAOYSA-N 3-[cyclopropyl-[3-[(4-fluorophenyl)sulfonylmethyl]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=2C=CC(F)=CC=2)C=CC=1)C1CC1 BBCYXBCXEQADSJ-UHFFFAOYSA-N 0.000 description 1
• IHKDKRYMCIBKJF-UHFFFAOYSA-N 3-[cyclopropyl-[3-[(4-methylphenyl)sulfonylmethyl]phenyl]methyl]-4-hydroxy-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-2-one Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CC1=CC=CC(C(C2CC2)C=2C(OC=3CCCCCCC=3C=2O)=O)=C1 IHKDKRYMCIBKJF-UHFFFAOYSA-N 0.000 description 1
• QPUOFVDFJAKWSX-UHFFFAOYSA-N 3-benzhydryl-4-hydroxychromen-2-one Chemical compound O=C1OC=2C=CC=CC=2C(O)=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 QPUOFVDFJAKWSX-UHFFFAOYSA-N 0.000 description 1
• HCSXSNXJWZXWOR-UHFFFAOYSA-N 3-benzyl-4-hydroxy-5,6,7,8-tetrahydrochromen-2-one Chemical compound O=C1OC=2CCCCC=2C(O)=C1CC1=CC=CC=C1 HCSXSNXJWZXWOR-UHFFFAOYSA-N 0.000 description 1
• HIJNOQRJBQXGFD-UHFFFAOYSA-N 3-benzyl-4-hydroxy-5-methyl-8-propan-2-yl-5,6,7,8-tetrahydrochromen-2-one Chemical compound O=C1OC=2C(C(C)C)CCC(C)C=2C(O)=C1CC1=CC=CC=C1 HIJNOQRJBQXGFD-UHFFFAOYSA-N 0.000 description 1
• NVAKEBUSGADONI-UHFFFAOYSA-N 3-benzyl-4-hydroxy-6-(3-methylphenyl)-7-phenyl-7h-pyrano[2,3-c]pyrrole-2,5-dione Chemical compound CC1=CC=CC(N2C(C=3C(O)=C(CC=4C=CC=CC=4)C(=O)OC=3C2C=2C=CC=CC=2)=O)=C1 NVAKEBUSGADONI-UHFFFAOYSA-N 0.000 description 1
• IJQKBVRKQSPTOM-UHFFFAOYSA-N 3-benzyl-4-hydroxy-9bh-indeno[1,2-b]pyran-2-one Chemical compound O=C1OC(C2=CC=CC=C2C=2)C=2C(O)=C1CC1=CC=CC=C1 IJQKBVRKQSPTOM-UHFFFAOYSA-N 0.000 description 1
• DCVIMWRFFDRWJM-UHFFFAOYSA-N 3-but-2-enoyl-4-phenyl-1,3-oxazolidin-2-one Chemical compound C1OC(=O)N(C(=O)C=CC)C1C1=CC=CC=C1 DCVIMWRFFDRWJM-UHFFFAOYSA-N 0.000 description 1
• TYBPYMSSRRRYRQ-UHFFFAOYSA-N 3-hexyl-6-undecyloxane-2,4-dione Chemical compound CCCCCCCCCCCC1CC(=O)C(CCCCCC)C(=O)O1 TYBPYMSSRRRYRQ-UHFFFAOYSA-N 0.000 description 1
• LZWAKBFDVSWNJO-UHFFFAOYSA-N 3-nitrosochromen-2-one Chemical compound C1=CC=C2OC(=O)C(N=O)=CC2=C1 LZWAKBFDVSWNJO-UHFFFAOYSA-N 0.000 description 1
• YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 1
• 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• AOCROEIFZQWEJI-UHFFFAOYSA-N 3-propanoylchromen-2-one Chemical compound C1=CC=C2OC(=O)C(C(=O)CC)=CC2=C1 AOCROEIFZQWEJI-UHFFFAOYSA-N 0.000 description 1
• DPYHGUIDBOZDPO-UHFFFAOYSA-N 4,7-dihydroxy-3-[4-(2-methoxyphenyl)butyl]chromen-2-one Chemical compound COC1=CC=CC=C1CCCCC1=C(O)C2=CC=C(O)C=C2OC1=O DPYHGUIDBOZDPO-UHFFFAOYSA-N 0.000 description 1
• MQLFSPBSNWUXSO-UHFFFAOYSA-N 4-(iodomethyl)oxane Chemical compound ICC1CCOCC1 MQLFSPBSNWUXSO-UHFFFAOYSA-N 0.000 description 1
• LRCFPRBBUORYJT-UHFFFAOYSA-N 4-[(4-hydroxy-5-methyl-6-oxo-2,3-dihydropyran-2-yl)methyl]piperidine-2,6-dione Chemical compound O1C(=O)C(C)=C(O)CC1CC1CC(=O)NC(=O)C1 LRCFPRBBUORYJT-UHFFFAOYSA-N 0.000 description 1
• DJIHQKUFYTXKJR-UHFFFAOYSA-N 4-[[3-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-3-yl)methyl]phenyl]methylsulfonyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)CC1=CC=CC(C(C2CC2)C=2C(OC=3CCCCCCC=3C=2O)=O)=C1 DJIHQKUFYTXKJR-UHFFFAOYSA-N 0.000 description 1
• SBKIEJFHYVAIJT-UHFFFAOYSA-N 4-[[3-[cyclopropyl-(4-hydroxy-2-oxo-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-3-yl)methyl]phenyl]methylsulfonyl]benzonitrile Chemical compound OC=1C=2CCCCCCC=2OC(=O)C=1C(C=1C=C(CS(=O)(=O)C=2C=CC(=CC=2)C#N)C=CC=1)C1CC1 SBKIEJFHYVAIJT-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• OJOFMLDBXPDXLQ-UHFFFAOYSA-N 4-benzyl-1,3-oxazolidin-2-one Chemical compound C1OC(=O)NC1CC1=CC=CC=C1 OJOFMLDBXPDXLQ-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• UOXPFOXNUVDMBP-UHFFFAOYSA-N 4-cyano-n-[3-[1-(4-hydroxy-6-oxo-2,2-dipentyl-3h-pyran-5-yl)propyl]phenyl]benzenesulfonamide Chemical compound O=C1OC(CCCCC)(CCCCC)CC(O)=C1C(CC)C1=CC=CC(NS(=O)(=O)C=2C=CC(=CC=2)C#N)=C1 UOXPFOXNUVDMBP-UHFFFAOYSA-N 0.000 description 1
• HSKYBHCOFAFSRZ-UHFFFAOYSA-N 4-cyano-n-[3-[cyclopropyl-[4-hydroxy-6-[1-(2-methoxyethoxy)pentan-3-yl]-2-oxopyran-3-yl]methyl]phenyl]benzenesulfonamide Chemical compound O=C1OC(C(CCOCCOC)CC)=CC(O)=C1C(C=1C=C(NS(=O)(=O)C=2C=CC(=CC=2)C#N)C=CC=1)C1CC1 HSKYBHCOFAFSRZ-UHFFFAOYSA-N 0.000 description 1
• AZRRZGIBBLWSSQ-UHFFFAOYSA-N 4-ethyl-7-phenyl-3,5-diazabicyclo[2.2.2]octane-2,6-dione Chemical compound N1C(=O)C2C(=O)NC1(CC)CC2C1=CC=CC=C1 AZRRZGIBBLWSSQ-UHFFFAOYSA-N 0.000 description 1
• UOQXIWFBQSVDPP-UHFFFAOYSA-N 4-fluorobenzaldehyde Chemical compound FC1=CC=C(C=O)C=C1 UOQXIWFBQSVDPP-UHFFFAOYSA-N 0.000 description 1
• OGXJERAKZKFBHR-UHFFFAOYSA-N 4-hydroxy-10-propylcycloocta[b]pyran-2-one Chemical compound CCCC1=CC=CC=CC2=C1OC(=O)C=C2O OGXJERAKZKFBHR-UHFFFAOYSA-N 0.000 description 1
• NJGFHHXZSDLYQJ-UHFFFAOYSA-N 4-hydroxy-2,3-dihydropyran-6-one Chemical compound OC1=CC(=O)OCC1 NJGFHHXZSDLYQJ-UHFFFAOYSA-N 0.000 description 1
• BQCOYEHIANYPOM-UHFFFAOYSA-N 4-hydroxy-2-(2-phenylethyl)-2-propyl-3h-pyran-6-one Chemical compound C=1C=CC=CC=1CCC1(CCC)CC(O)=CC(=O)O1 BQCOYEHIANYPOM-UHFFFAOYSA-N 0.000 description 1
• KHVQTGWQUCCIQA-UHFFFAOYSA-N 4-hydroxy-3-(1-phenylpentyl)chromen-2-one Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CCCC)C1=CC=CC=C1 KHVQTGWQUCCIQA-UHFFFAOYSA-N 0.000 description 1
• AYMUNURORFMGDI-UHFFFAOYSA-N 4-hydroxy-3-(1-phenylprop-1-enyl)chromen-2-one Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(=CC)C1=CC=CC=C1 AYMUNURORFMGDI-UHFFFAOYSA-N 0.000 description 1
• XKRJRNUOWCGSIL-UHFFFAOYSA-N 4-hydroxy-3-(2-methyl-1-phenylpropyl)chromen-2-one Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(C(C)C)C1=CC=CC=C1 XKRJRNUOWCGSIL-UHFFFAOYSA-N 0.000 description 1
• ZUJMMGHIYSAEOU-UHFFFAOYSA-N 4-hydroxy-3-(3-hydroxy-1-phenylbutyl)-2H-chromen-2-one Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(O)C)C1=CC=CC=C1 ZUJMMGHIYSAEOU-UHFFFAOYSA-N 0.000 description 1
• YSDYVLZGWHIINQ-UHFFFAOYSA-N 4-hydroxy-3-(3-methyl-1-phenylbutyl)chromen-2-one Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC(C)C)C1=CC=CC=C1 YSDYVLZGWHIINQ-UHFFFAOYSA-N 0.000 description 1
• VXUWMCOXJJOIBU-UHFFFAOYSA-N 4-hydroxy-3-[(2,4,6-trihydroxyphenyl)methyl]pyran-2-one Chemical class OC1=CC(O)=CC(O)=C1CC1=C(O)C=COC1=O VXUWMCOXJJOIBU-UHFFFAOYSA-N 0.000 description 1
• QWCUMICDGVLTKR-UHFFFAOYSA-N 4-hydroxy-3-[(2-hydroxy-3,5-dimethylphenyl)methyl]-5,6,7,8-tetrahydrochromen-2-one Chemical compound CC1=CC(C)=C(O)C(CC=2C(OC=3CCCCC=3C=2O)=O)=C1 QWCUMICDGVLTKR-UHFFFAOYSA-N 0.000 description 1
• GBRIBSUSLRTIHH-UHFFFAOYSA-N 4-hydroxy-3-[1-(3-hydroxyphenyl)propyl]chromen-2-one Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC)C1=CC=CC(O)=C1 GBRIBSUSLRTIHH-UHFFFAOYSA-N 0.000 description 1
• DVPBQNDNILIJKS-UHFFFAOYSA-N 4-hydroxy-3-[1-(3-phenylmethoxyphenyl)propyl]chromen-2-one Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC)C(C=1)=CC=CC=1OCC1=CC=CC=C1 DVPBQNDNILIJKS-UHFFFAOYSA-N 0.000 description 1
• DVPVLAJHNXWKAQ-UHFFFAOYSA-N 4-hydroxy-3-[1-(4-methoxyphenyl)-3-(4-nitrophenyl)prop-2-enyl]-6-methylpyran-2-one Chemical compound C1=CC(OC)=CC=C1C(C=1C(OC(C)=CC=1O)=O)C=CC1=CC=C([N+]([O-])=O)C=C1 DVPVLAJHNXWKAQ-UHFFFAOYSA-N 0.000 description 1
• TYUIFWKSYAYHOR-UHFFFAOYSA-N 4-hydroxy-3-[1-(4-methoxyphenyl)propyl]chromen-2-one Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CC)C1=CC=C(OC)C=C1 TYUIFWKSYAYHOR-UHFFFAOYSA-N 0.000 description 1
• UIJGATCWTZHBSJ-UHFFFAOYSA-N 4-hydroxy-3-[1-(4-methylphenyl)butyl]chromen-2-one Chemical compound OC=1C2=CC=CC=C2OC(=O)C=1C(CCC)C1=CC=C(C)C=C1 UIJGATCWTZHBSJ-UHFFFAOYSA-N 0.000 description 1
• MXAXSAZNXMFLQD-UHFFFAOYSA-N 4-hydroxy-3-[3-(4-methoxyphenyl)-1-(4-nitrophenyl)prop-2-enyl]-6-methylpyran-2-one Chemical compound C1=CC(OC)=CC=C1C=CC(C=1C(OC(C)=CC=1O)=O)C1=CC=C([N+]([O-])=O)C=C1 MXAXSAZNXMFLQD-UHFFFAOYSA-N 0.000 description 1
• BOYQHDVXWSILRJ-UHFFFAOYSA-N 4-hydroxy-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-2-one Chemical compound C1CCCCCC2=C1OC(=O)C=C2O BOYQHDVXWSILRJ-UHFFFAOYSA-N 0.000 description 1
• XBMJBISBCODORE-UHFFFAOYSA-N 4-hydroxy-5-[1-(3-nitrophenyl)propyl]-2,2-dipropyl-3h-pyran-6-one Chemical compound O=C1OC(CCC)(CCC)CC(O)=C1C(CC)C1=CC=CC([N+]([O-])=O)=C1 XBMJBISBCODORE-UHFFFAOYSA-N 0.000 description 1
• IVSBNHGCCSIIRX-UHFFFAOYSA-N 4-hydroxy-5-[1-(3-nitrophenyl)propyl]-2-(2-phenylethyl)-2-propyl-3h-pyran-6-one Chemical compound C1C(O)=C(C(CC)C=2C=C(C=CC=2)[N+]([O-])=O)C(=O)OC1(CCC)CCC1=CC=CC=C1 IVSBNHGCCSIIRX-UHFFFAOYSA-N 0.000 description 1
• HWOWEGAQDKKHDR-UHFFFAOYSA-N 4-hydroxy-6-(pyridin-3-yl)-2H-pyran-2-one Chemical compound O1C(=O)C=C(O)C=C1C1=CC=CN=C1 HWOWEGAQDKKHDR-UHFFFAOYSA-N 0.000 description 1
• WRXVWMCXFUOVBU-UHFFFAOYSA-N 4-hydroxy-6-[3-(2-methoxyethoxy)propyl]pyran-2-one Chemical compound COCCOCCCC1=CC(O)=CC(=O)O1 WRXVWMCXFUOVBU-UHFFFAOYSA-N 0.000 description 1
• OTWFKTVKTRQRNO-UHFFFAOYSA-N 4-hydroxy-6-methoxy-3-(1-phenylpropyl)chromen-2-one Chemical compound OC=1C2=CC(OC)=CC=C2OC(=O)C=1C(CC)C1=CC=CC=C1 OTWFKTVKTRQRNO-UHFFFAOYSA-N 0.000 description 1
• IIVCYYLSRRSAII-UHFFFAOYSA-N 4-hydroxy-6-methyl-3-(3-phenylprop-2-enyl)pyran-2-one Chemical compound O=C1OC(C)=CC(O)=C1CC=CC1=CC=CC=C1 IIVCYYLSRRSAII-UHFFFAOYSA-N 0.000 description 1
• IOFIOWLRZOQXNF-UHFFFAOYSA-N 4-hydroxy-6-phenyl-3-phenylsulfanylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1SC1=CC=CC=C1 IOFIOWLRZOQXNF-UHFFFAOYSA-N 0.000 description 1
• QMKINTXOUGERDI-UHFFFAOYSA-N 4-hydroxy-7-methyl-3-(1-phenylpropyl)chromen-2-one Chemical compound OC=1C2=CC=C(C)C=C2OC(=O)C=1C(CC)C1=CC=CC=C1 QMKINTXOUGERDI-UHFFFAOYSA-N 0.000 description 1
• MCMUGWFOOPVKSF-UHFFFAOYSA-N 4-hydroxy-8-phenylmethoxy-3-(1-phenylpropyl)chromen-2-one Chemical compound OC=1C2=CC=CC(OCC=3C=CC=CC=3)=C2OC(=O)C=1C(CC)C1=CC=CC=C1 MCMUGWFOOPVKSF-UHFFFAOYSA-N 0.000 description 1
• GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical compound OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 description 1
• QDMNNMIOWVJVLY-UHFFFAOYSA-N 4-phenyl-1,3-oxazolidin-2-one Chemical compound C1OC(=O)NC1C1=CC=CC=C1 QDMNNMIOWVJVLY-UHFFFAOYSA-N 0.000 description 1
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
• PRLATKYVVWJECP-UHFFFAOYSA-N 5,6-dihydroxypyran-2-one Chemical compound OC=1C=CC(=O)OC=1O PRLATKYVVWJECP-UHFFFAOYSA-N 0.000 description 1
• RTBSCIQDEJVUMV-UHFFFAOYSA-N 5-[1-(3-aminophenyl)propyl]-4-hydroxy-2-(2-phenylethyl)-2-propyl-3h-pyran-6-one Chemical compound C1C(O)=C(C(CC)C=2C=C(N)C=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 RTBSCIQDEJVUMV-UHFFFAOYSA-N 0.000 description 1
• KWBLKKAHBRSRBV-UHFFFAOYSA-N 5-[cyclopropyl-(3-nitrophenyl)methyl]-4-hydroxy-2-(2-phenylethyl)-2-propyl-3h-pyran-6-one Chemical compound C1C(O)=C(C(C2CC2)C=2C=C(C=CC=2)[N+]([O-])=O)C(=O)OC1(CCC)CCC1=CC=CC=C1 KWBLKKAHBRSRBV-UHFFFAOYSA-N 0.000 description 1
• NQSWUAAKHLJOAW-UHFFFAOYSA-N 5-hexyl-2-pentyl-2,3-dihydropyran-6-one Chemical compound CCCCCCC1=CCC(CCCCC)OC1=O NQSWUAAKHLJOAW-UHFFFAOYSA-N 0.000 description 1
• OXCNCNSXYNPTOC-UHFFFAOYSA-N 5-sulfanylpyran-2-one Chemical compound Sc1ccc(=O)oc1 OXCNCNSXYNPTOC-UHFFFAOYSA-N 0.000 description 1
• OPDXKSNOBHSQGU-UHFFFAOYSA-N 6-(1,3-dicyclopropylpropan-2-yl)-4-hydroxypyran-2-one Chemical compound O1C(=O)C=C(O)C=C1C(CC1CC1)CC1CC1 OPDXKSNOBHSQGU-UHFFFAOYSA-N 0.000 description 1
• 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 description 1
• QHXUTZKOUDJTIY-UHFFFAOYSA-N 6-amino-1,5-dibenzylcyclohexa-2,4-diene-1-carboxylic acid Chemical compound C(C1=CC=CC=C1)C1(C(=O)O)C(C(=CC=C1)CC1=CC=CC=C1)N QHXUTZKOUDJTIY-UHFFFAOYSA-N 0.000 description 1
• ZOJAINJCZSVZGW-UHFFFAOYSA-N 6-aminochromen-2-one Chemical compound O1C(=O)C=CC2=CC(N)=CC=C21 ZOJAINJCZSVZGW-UHFFFAOYSA-N 0.000 description 1
• OBAWNXJOHPSFMJ-UHFFFAOYSA-N 6-but-2-en-2-yl-4-hydroxy-3-methylpyran-2-one Chemical compound CC=C(C)C1=CC(O)=C(C)C(=O)O1 OBAWNXJOHPSFMJ-UHFFFAOYSA-N 0.000 description 1
• PWSJCBQLHHENIG-UHFFFAOYSA-N 6-sulfanylidene-1h-pyridine-3-carboxamide Chemical compound NC(=O)C=1C=CC(=S)NC=1 PWSJCBQLHHENIG-UHFFFAOYSA-N 0.000 description 1
• IIRWTUYKOTUXHV-UHFFFAOYSA-N 7-chloro-4-hydroxy-3-(1-phenylpropyl)chromen-2-one Chemical compound OC=1C2=CC=C(Cl)C=C2OC(=O)C=1C(CC)C1=CC=CC=C1 IIRWTUYKOTUXHV-UHFFFAOYSA-N 0.000 description 1
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
• CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
• SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 1
• 208000029483 Acquired immunodeficiency Diseases 0.000 description 1
• 241000416162 Astragalus gummifer Species 0.000 description 1
• 108090001008 Avidin Proteins 0.000 description 1
• 241000894006 Bacteria Species 0.000 description 1
• 239000005711 Benzoic acid Substances 0.000 description 1
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
• UJOGXLWYTULNJP-UHFFFAOYSA-N C1(=CC=CC=C1)C=1N(C=C(N=1)S(=O)(=O)N)C Chemical compound C1(=CC=CC=C1)C=1N(C=C(N=1)S(=O)(=O)N)C UJOGXLWYTULNJP-UHFFFAOYSA-N 0.000 description 1
• ASXFYAWGKUZAHN-UHFFFAOYSA-N CCCC(=O)C1=C(O)CC(C)(C(C)=CC)OC1=O Chemical compound CCCC(=O)C1=C(O)CC(C)(C(C)=CC)OC1=O ASXFYAWGKUZAHN-UHFFFAOYSA-N 0.000 description 1
• 210000004366 CD4-positive T-lymphocyte Anatomy 0.000 description 1
• 101100172118 Caenorhabditis elegans eif-2Bgamma gene Proteins 0.000 description 1
• 241000606161 Chlamydia Species 0.000 description 1
• 101710094648 Coat protein Proteins 0.000 description 1
• RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
• 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
• 241000699802 Cricetulus griseus Species 0.000 description 1
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
• 241000701022 Cytomegalovirus Species 0.000 description 1
• HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
• 102000004163 DNA-directed RNA polymerases Human genes 0.000 description 1
• 108090000626 DNA-directed RNA polymerases Proteins 0.000 description 1
• 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
• OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
• QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
• 241001269524 Dura Species 0.000 description 1
• 239000004593 Epoxy Substances 0.000 description 1
• 102100039250 Essential MCU regulator, mitochondrial Human genes 0.000 description 1
• 241000713800 Feline immunodeficiency virus Species 0.000 description 1
• 241000711475 Feline infectious peritonitis virus Species 0.000 description 1
• 241000714165 Feline leukemia virus Species 0.000 description 1
• 241000701925 Feline parvovirus Species 0.000 description 1
• 241000282324 Felis Species 0.000 description 1
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
• 230000005526 G1 to G0 transition Effects 0.000 description 1
• 239000001828 Gelatine Substances 0.000 description 1
• CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical class OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
• 108090000288 Glycoproteins Proteins 0.000 description 1
• 102000003886 Glycoproteins Human genes 0.000 description 1
• 208000037357 HIV infectious disease Diseases 0.000 description 1
• 229940126544 HIV-1 protease inhibitor Drugs 0.000 description 1
• 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 1
• 101000813097 Homo sapiens Essential MCU regulator, mitochondrial Proteins 0.000 description 1
• 206010020460 Human T-cell lymphotropic virus type I infection Diseases 0.000 description 1
• 241000701044 Human gammaherpesvirus 4 Species 0.000 description 1
• 241000713340 Human immunodeficiency virus 2 Species 0.000 description 1
• 108010016191 Human immunodeficiency virus 2 p16 protease Proteins 0.000 description 1
• XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 1
• 206010061598 Immunodeficiency Diseases 0.000 description 1
• 208000029462 Immunodeficiency disease Diseases 0.000 description 1
• 102000012330 Integrases Human genes 0.000 description 1
• 108010061833 Integrases Proteins 0.000 description 1
• 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
• 229930194542 Keto Natural products 0.000 description 1
• ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
• GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
• 206010067125 Liver injury Diseases 0.000 description 1
• 206010027476 Metastases Diseases 0.000 description 1
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
• 101100457407 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) mmm-1 gene Proteins 0.000 description 1
• 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
• QSQXRFCSHADOCP-UHFFFAOYSA-N O1C(=O)C(C(=O)CCC)=C(O)CC1(C)C1CC1 Chemical compound O1C(=O)C(C(=O)CCC)=C(O)CC1(C)C1CC1 QSQXRFCSHADOCP-UHFFFAOYSA-N 0.000 description 1
• 208000001388 Opportunistic Infections Diseases 0.000 description 1
• 206010033645 Pancreatitis Diseases 0.000 description 1
• 108090000284 Pepsin A Proteins 0.000 description 1
• 102000057297 Pepsin A Human genes 0.000 description 1
• 239000004264 Petrolatum Substances 0.000 description 1
• 108010076039 Polyproteins Proteins 0.000 description 1
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
• 108010029485 Protein Isoforms Proteins 0.000 description 1
• 102000001708 Protein Isoforms Human genes 0.000 description 1
• 102100027378 Prothrombin Human genes 0.000 description 1
• 108010094028 Prothrombin Proteins 0.000 description 1
• YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
• CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical compound O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 description 1
• 241000711798 Rabies lyssavirus Species 0.000 description 1
• 102100028255 Renin Human genes 0.000 description 1
• 108090000783 Renin Proteins 0.000 description 1
• PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 1
• 241000283984 Rodentia Species 0.000 description 1
• 206010039491 Sarcoma Diseases 0.000 description 1
• 238000012300 Sequence Analysis Methods 0.000 description 1
• 238000006202 Sharpless epoxidation reaction Methods 0.000 description 1
• 229920002472 Starch Polymers 0.000 description 1
• 241000187747 Streptomyces Species 0.000 description 1
• 229930006000 Sucrose Natural products 0.000 description 1
• CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
• UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
• 229920001615 Tragacanth Polymers 0.000 description 1
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
• 108020000999 Viral RNA Proteins 0.000 description 1
• 208000036142 Viral infection Diseases 0.000 description 1
• DILVWDXOASDRPN-MROZADKFSA-N [(2r,3r,4r)-3,4,5-trihydroxy-1-oxopentan-2-yl] dihydrogen phosphate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](C=O)OP(O)(O)=O DILVWDXOASDRPN-MROZADKFSA-N 0.000 description 1
• FKXCNOSKBLGEMQ-SNAWJCMRSA-N [(e)-2-bromoethenyl]-trimethylsilane Chemical compound C[Si](C)(C)\C=C\Br FKXCNOSKBLGEMQ-SNAWJCMRSA-N 0.000 description 1
• NGCUKAMJVZKNPN-UHFFFAOYSA-N [3-(1-hydroxy-3-methylbutyl)phenyl]carbamic acid Chemical compound CC(C)CC(O)C1=CC=CC(NC(O)=O)=C1 NGCUKAMJVZKNPN-UHFFFAOYSA-N 0.000 description 1
• RKFJLAMKBRRYJG-UHFFFAOYSA-M [Br-].[Mg+]CCC1=CC=CC=C1 Chemical compound [Br-].[Mg+]CCC1=CC=CC=C1 RKFJLAMKBRRYJG-UHFFFAOYSA-M 0.000 description 1
• 230000002159 abnormal effect Effects 0.000 description 1
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
• 238000010306 acid treatment Methods 0.000 description 1
• 150000008043 acidic salts Chemical class 0.000 description 1
• 230000009471 action Effects 0.000 description 1
• YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
• 150000001447 alkali salts Chemical class 0.000 description 1
• 125000003342 alkenyl group Chemical group 0.000 description 1
• 150000004703 alkoxides Chemical class 0.000 description 1
• 150000001350 alkyl halides Chemical class 0.000 description 1
• HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 1
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
• SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
• 125000000539 amino acid group Chemical class 0.000 description 1
• 125000003277 amino group Chemical group 0.000 description 1
• 239000003708 ampul Substances 0.000 description 1
• 238000004458 analytical method Methods 0.000 description 1
• 239000000538 analytical sample Substances 0.000 description 1
• 125000000129 anionic group Chemical group 0.000 description 1
• 239000003242 anti bacterial agent Substances 0.000 description 1
• 230000001093 anti-cancer Effects 0.000 description 1
• 230000002429 anti-coagulating effect Effects 0.000 description 1
• 230000000843 anti-fungal effect Effects 0.000 description 1
• 229940088710 antibiotic agent Drugs 0.000 description 1
• 239000002246 antineoplastic agent Substances 0.000 description 1
• 239000003096 antiparasitic agent Substances 0.000 description 1
• 229940125687 antiparasitic agent Drugs 0.000 description 1
• 239000003698 antivitamin K Substances 0.000 description 1
• 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
• 125000005110 aryl thio group Chemical group 0.000 description 1
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
• 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
• CVIJNQKLULWJQI-UHFFFAOYSA-N benzyl n-[3-[cyclopropyl-[6-[2-(1-ethylcyclohexa-2,4-dien-1-yl)ethyl]-4-hydroxy-2-oxopyran-3-yl]methyl]phenyl]carbamate Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NC(=O)OCC=3C=CC=CC=3)C=CC=2)C(=O)OC=1CCC1(CC)CC=CC=C1 CVIJNQKLULWJQI-UHFFFAOYSA-N 0.000 description 1
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
• ZDWYFWIBTZJGOR-UHFFFAOYSA-N bis(trimethylsilyl)acetylene Chemical group C[Si](C)(C)C#C[Si](C)(C)C ZDWYFWIBTZJGOR-UHFFFAOYSA-N 0.000 description 1
• 230000000903 blocking effect Effects 0.000 description 1
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
• 239000000872 buffer Substances 0.000 description 1
• 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 239000001506 calcium phosphate Substances 0.000 description 1
• 201000011510 cancer Diseases 0.000 description 1
• 235000013877 carbamide Nutrition 0.000 description 1
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
• 238000002512 chemotherapy Methods 0.000 description 1
• 150000001805 chlorine compounds Chemical class 0.000 description 1
• 125000001309 chloro group Chemical group Cl* 0.000 description 1
• WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
• 150000004777 chromones Chemical class 0.000 description 1
• 238000004590 computer program Methods 0.000 description 1
• 239000012141 concentrate Substances 0.000 description 1
• 235000008504 concentrate Nutrition 0.000 description 1
• 238000006482 condensation reaction Methods 0.000 description 1
• 230000021615 conjugation Effects 0.000 description 1
• 238000007796 conventional method Methods 0.000 description 1
• 239000010949 copper Substances 0.000 description 1
• 229910052802 copper Inorganic materials 0.000 description 1
• OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
• ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
• 230000008878 coupling Effects 0.000 description 1
• 238000010168 coupling process Methods 0.000 description 1
• 238000005859 coupling reaction Methods 0.000 description 1
• 239000013058 crude material Substances 0.000 description 1
• 239000012043 crude product Substances 0.000 description 1
• 229940045803 cuprous chloride Drugs 0.000 description 1
• 125000004802 cyanophenyl group Chemical group 0.000 description 1
• 150000001923 cyclic compounds Chemical class 0.000 description 1
• 229960002944 cyclofenil Drugs 0.000 description 1
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
• IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical compound O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 description 1
• LZQOJEMORXEICJ-UHFFFAOYSA-N cyclopropyl-[3-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=CC(C(O)C2CC2)=C1 LZQOJEMORXEICJ-UHFFFAOYSA-N 0.000 description 1
• 239000000824 cytostatic agent Substances 0.000 description 1
• 230000001085 cytostatic effect Effects 0.000 description 1
• 231100000599 cytotoxic agent Toxicity 0.000 description 1
• 239000002619 cytotoxin Substances 0.000 description 1
• 238000005828 desilylation reaction Methods 0.000 description 1
• 238000011161 development Methods 0.000 description 1
• 230000018109 developmental process Effects 0.000 description 1
• 150000004985 diamines Chemical class 0.000 description 1
• NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
• 229940038472 dicalcium phosphate Drugs 0.000 description 1
• 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
• ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 description 1
• YSAVZVORKRDODB-PHDIDXHHSA-N diethyl (2r,3r)-2,3-dihydroxybutanedioate Chemical compound CCOC(=O)[C@H](O)[C@@H](O)C(=O)OCC YSAVZVORKRDODB-PHDIDXHHSA-N 0.000 description 1
• YSAVZVORKRDODB-WDSKDSINSA-N diethyl tartrate Chemical compound CCOC(=O)[C@@H](O)[C@H](O)C(=O)OCC YSAVZVORKRDODB-WDSKDSINSA-N 0.000 description 1
• NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
• BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 description 1
• 238000010790 dilution Methods 0.000 description 1
• 239000012895 dilution Substances 0.000 description 1
• 239000006185 dispersion Substances 0.000 description 1
• 239000003937 drug carrier Substances 0.000 description 1
• 238000009510 drug design Methods 0.000 description 1
• 238000006735 epoxidation reaction Methods 0.000 description 1
• IEARPTNIYZTWOZ-UHFFFAOYSA-N ethene Chemical compound [CH-]=C IEARPTNIYZTWOZ-UHFFFAOYSA-N 0.000 description 1
• 239000004210 ether based solvent Substances 0.000 description 1
• 238000006266 etherification reaction Methods 0.000 description 1
• PSRZMXNNQTWAGB-UHFFFAOYSA-N ethyl 4,4,4-trifluorobutanoate Chemical compound CCOC(=O)CCC(F)(F)F PSRZMXNNQTWAGB-UHFFFAOYSA-N 0.000 description 1
• 235000010228 ethyl p-hydroxybenzoate Nutrition 0.000 description 1
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
• 230000001747 exhibiting effect Effects 0.000 description 1
• 238000011049 filling Methods 0.000 description 1
• 229930003944 flavone Natural products 0.000 description 1
• 150000002213 flavones Chemical class 0.000 description 1
• 235000011949 flavones Nutrition 0.000 description 1
• 235000019634 flavors Nutrition 0.000 description 1
• 239000012530 fluid Substances 0.000 description 1
• 239000011737 fluorine Substances 0.000 description 1
• 229910052731 fluorine Inorganic materials 0.000 description 1
• 235000013355 food flavoring agent Nutrition 0.000 description 1
• WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
• 108700004026 gag Genes Proteins 0.000 description 1
• 108010027225 gag-pol Fusion Proteins Proteins 0.000 description 1
• 229920000159 gelatin Polymers 0.000 description 1
• 239000007903 gelatin capsule Substances 0.000 description 1
• 235000019322 gelatine Nutrition 0.000 description 1
• 230000008570 general process Effects 0.000 description 1
• 229930192428 germicidin Natural products 0.000 description 1
• 230000035784 germination Effects 0.000 description 1
• 230000034659 glycolysis Effects 0.000 description 1
• 230000036541 health Effects 0.000 description 1
• 231100000234 hepatic damage Toxicity 0.000 description 1
• 230000002440 hepatic effect Effects 0.000 description 1
• UONLQSKINPCMDF-UHFFFAOYSA-N hepta-1,6-diyn-4-one Chemical compound C#CCC(=O)CC#C UONLQSKINPCMDF-UHFFFAOYSA-N 0.000 description 1
• 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
• 238000004128 high performance liquid chromatography Methods 0.000 description 1
• 238000004896 high resolution mass spectrometry Methods 0.000 description 1
• 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
• 150000004677 hydrates Chemical class 0.000 description 1
• 150000003840 hydrochlorides Chemical class 0.000 description 1
• 229910000039 hydrogen halide Inorganic materials 0.000 description 1
• 239000012433 hydrogen halide Substances 0.000 description 1
• 238000007327 hydrogenolysis reaction Methods 0.000 description 1
• 230000003301 hydrolyzing effect Effects 0.000 description 1
• 150000002440 hydroxy compounds Chemical class 0.000 description 1
• 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 1
• 230000007813 immunodeficiency Effects 0.000 description 1
• 230000001771 impaired effect Effects 0.000 description 1
• 238000000338 in vitro Methods 0.000 description 1
• 206010022000 influenza Diseases 0.000 description 1
• 238000001802 infusion Methods 0.000 description 1
• 239000004615 ingredient Substances 0.000 description 1
• 230000003993 interaction Effects 0.000 description 1
• 238000007918 intramuscular administration Methods 0.000 description 1
• 229910052740 iodine Inorganic materials 0.000 description 1
• 239000011630 iodine Substances 0.000 description 1
• HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
• 229910052742 iron Inorganic materials 0.000 description 1
• RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
• 230000002427 irreversible effect Effects 0.000 description 1
• 150000002540 isothiocyanates Chemical class 0.000 description 1
• 239000008101 lactose Substances 0.000 description 1
• JNODQFNWMXFMEV-UHFFFAOYSA-N latrepirdine Chemical compound C1N(C)CCC2=C1C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1 JNODQFNWMXFMEV-UHFFFAOYSA-N 0.000 description 1
• MLTFKRDFAJSIEX-UHFFFAOYSA-N lithium;1,3-oxazolidin-2-one Chemical compound [Li].O=C1NCCO1 MLTFKRDFAJSIEX-UHFFFAOYSA-N 0.000 description 1
• 230000008818 liver damage Effects 0.000 description 1
• 229910001629 magnesium chloride Inorganic materials 0.000 description 1
• 235000019359 magnesium stearate Nutrition 0.000 description 1
• YSMZEMQBSONIMJ-UHFFFAOYSA-M magnesium;2-methanidylpropane;chloride Chemical compound [Mg+2].[Cl-].CC(C)[CH2-] YSMZEMQBSONIMJ-UHFFFAOYSA-M 0.000 description 1
• JAUWOQLHLFMTON-UHFFFAOYSA-M magnesium;but-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]CC=C JAUWOQLHLFMTON-UHFFFAOYSA-M 0.000 description 1
• VFZXMEQGIIWBFJ-UHFFFAOYSA-M magnesium;cyclopropane;bromide Chemical compound [Mg+2].[Br-].C1C[CH-]1 VFZXMEQGIIWBFJ-UHFFFAOYSA-M 0.000 description 1
• 150000002690 malonic acid derivatives Chemical class 0.000 description 1
• 210000004962 mammalian cell Anatomy 0.000 description 1
• 239000011159 matrix material Substances 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
• 229910052753 mercury Inorganic materials 0.000 description 1
• 229910052987 metal hydride Inorganic materials 0.000 description 1
• 150000004681 metal hydrides Chemical class 0.000 description 1
• 230000009401 metastasis Effects 0.000 description 1
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
• ZKUUVVYMPUDTGJ-UHFFFAOYSA-N methyl 5-hydroxy-4-methoxy-2-nitrobenzoate Chemical compound COC(=O)C1=CC(O)=C(OC)C=C1[N+]([O-])=O ZKUUVVYMPUDTGJ-UHFFFAOYSA-N 0.000 description 1
• XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
• 230000004048 modification Effects 0.000 description 1
• 238000012986 modification Methods 0.000 description 1
• 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
• 150000004682 monohydrates Chemical class 0.000 description 1
• 239000000178 monomer Substances 0.000 description 1
• MUMVIYLVHVCYGI-UHFFFAOYSA-N n,n,n',n',n",n"-hexamethylmethanetriamine Chemical compound CN(C)C(N(C)C)N(C)C MUMVIYLVHVCYGI-UHFFFAOYSA-N 0.000 description 1
• HXRAMSFGUAOAJR-UHFFFAOYSA-N n,n,n',n'-tetramethyl-1-[(2-methylpropan-2-yl)oxy]methanediamine Chemical compound CN(C)C(N(C)C)OC(C)(C)C HXRAMSFGUAOAJR-UHFFFAOYSA-N 0.000 description 1
• XFYPEKHCCSNYOX-UHFFFAOYSA-N n-[3-[[6-(1-aminopentan-3-yl)-4-hydroxy-2-oxopyran-3-yl]-cyclopropylmethyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound O=C1OC(C(CCN)CC)=CC(O)=C1C(C=1C=C(NS(=O)(=O)C=2N=CN(C)C=2)C=CC=1)C1CC1 XFYPEKHCCSNYOX-UHFFFAOYSA-N 0.000 description 1
• WCLOVPIZOCXRRF-UHFFFAOYSA-N n-[3-[[6-(3-amino-4-oxo-4-piperazin-1-ylbutyl)-4-hydroxy-2-oxopyran-3-yl]-cyclopropylmethyl]phenyl]-1-methylimidazole-2-sulfonamide Chemical compound CN1C=CN=C1S(=O)(=O)NC1=CC=CC(C(C2CC2)C=2C(OC(CCC(N)C(=O)N3CCNCC3)=CC=2O)=O)=C1 WCLOVPIZOCXRRF-UHFFFAOYSA-N 0.000 description 1
• OMWLSZKVAXZSNY-UHFFFAOYSA-N n-[3-[[6-(3-amino-4-oxo-4-piperazin-1-ylbutyl)-4-hydroxy-2-oxopyran-3-yl]-cyclopropylmethyl]phenyl]pyridine-2-sulfonamide Chemical compound C1CNCCN1C(=O)C(N)CCC(OC1=O)=CC(O)=C1C(C=1C=C(NS(=O)(=O)C=2N=CC=CC=2)C=CC=1)C1CC1 OMWLSZKVAXZSNY-UHFFFAOYSA-N 0.000 description 1
• XUDXPTHHNSJNLF-UHFFFAOYSA-N n-[3-[cyclopropyl-(4-hydroxy-2-oxo-10-propyl-5,6,7,8,9,10-hexahydrocycloocta[b]pyran-3-yl)methyl]phenyl]benzenesulfonamide Chemical compound O=C1OC=2C(CCC)CCCCCC=2C(O)=C1C(C=1C=C(NS(=O)(=O)C=2C=CC=CC=2)C=CC=1)C1CC1 XUDXPTHHNSJNLF-UHFFFAOYSA-N 0.000 description 1
• YIQMLPUYNLJPQY-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-7-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]-2-oxochromen-3-yl]methyl]phenyl]-1-methylimidazole-4-sulfonamide Chemical compound O=C1OC2=CC(OCCOCCOCCOC)=CC=C2C(O)=C1C(C=1C=C(NS(=O)(=O)C=2N=CN(C)C=2)C=CC=1)C1CC1 YIQMLPUYNLJPQY-UHFFFAOYSA-N 0.000 description 1
• 125000001624 naphthyl group Chemical group 0.000 description 1
• 201000009240 nasopharyngitis Diseases 0.000 description 1
• 230000003472 neutralizing effect Effects 0.000 description 1
• 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
• 230000000269 nucleophilic effect Effects 0.000 description 1
• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
• 125000002524 organometallic group Chemical group 0.000 description 1
• 210000001672 ovary Anatomy 0.000 description 1
• URUUZIAJVSGYRC-UHFFFAOYSA-N oxan-3-one Chemical compound O=C1CCCOC1 URUUZIAJVSGYRC-UHFFFAOYSA-N 0.000 description 1
• YSNVSVCWTBLLRW-UHFFFAOYSA-N oxan-4-ylmethanol Chemical compound OCC1CCOCC1 YSNVSVCWTBLLRW-UHFFFAOYSA-N 0.000 description 1
• DCBKCZSYJRZBDB-UHFFFAOYSA-N oxan-4-ylmethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC1CCOCC1 DCBKCZSYJRZBDB-UHFFFAOYSA-N 0.000 description 1
• 239000007800 oxidant agent Substances 0.000 description 1
• 230000001590 oxidative effect Effects 0.000 description 1
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
• PENAXHPKEVTBLF-UHFFFAOYSA-L palladium(2+);prop-1-ene;dichloride Chemical compound [Pd+]Cl.[Pd+]Cl.[CH2-]C=C.[CH2-]C=C PENAXHPKEVTBLF-UHFFFAOYSA-L 0.000 description 1
• 239000003182 parenteral nutrition solution Substances 0.000 description 1
• HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
• HVAMZGADVCBITI-UHFFFAOYSA-N pent-4-enoic acid Chemical compound OC(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-N 0.000 description 1
• 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
• 229940111202 pepsin Drugs 0.000 description 1
• 235000019271 petrolatum Nutrition 0.000 description 1
• 229940066842 petrolatum Drugs 0.000 description 1
• 239000008194 pharmaceutical composition Substances 0.000 description 1
• 239000012071 phase Substances 0.000 description 1
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
• UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
• 230000026731 phosphorylation Effects 0.000 description 1
• 238000006366 phosphorylation reaction Methods 0.000 description 1
• 125000001557 phthalyl group Chemical group C(=O)(O)C1=C(C(=O)*)C=CC=C1 0.000 description 1
• 230000001766 physiological effect Effects 0.000 description 1
• 108700004029 pol Genes Proteins 0.000 description 1
• NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
• 229910000105 potassium hydride Inorganic materials 0.000 description 1
• 159000000001 potassium salts Chemical class 0.000 description 1
• 230000003334 potential effect Effects 0.000 description 1
• 230000003389 potentiating effect Effects 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 230000002265 prevention Effects 0.000 description 1
• 230000002035 prolonged effect Effects 0.000 description 1
• 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
• 229940039716 prothrombin Drugs 0.000 description 1
• 230000005588 protonation Effects 0.000 description 1
• MERGMNQXULKBCH-UHFFFAOYSA-N pyran-2,4-dione Chemical compound O=C1CC(=O)C=CO1 MERGMNQXULKBCH-UHFFFAOYSA-N 0.000 description 1
• 229930185107 quinolinone Natural products 0.000 description 1
• 239000012217 radiopharmaceutical Substances 0.000 description 1
• 229940121896 radiopharmaceutical Drugs 0.000 description 1
• 230000002799 radiopharmaceutical effect Effects 0.000 description 1
• 239000000376 reactant Substances 0.000 description 1
• 239000005871 repellent Substances 0.000 description 1
• 230000002940 repellent Effects 0.000 description 1
• 230000002441 reversible effect Effects 0.000 description 1
• 238000012552 review Methods 0.000 description 1
• 206010039083 rhinitis Diseases 0.000 description 1
• 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 1
• 229960003522 roquinimex Drugs 0.000 description 1
• CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
• 235000019204 saccharin Nutrition 0.000 description 1
• 229940081974 saccharin Drugs 0.000 description 1
• 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
• 238000007423 screening assay Methods 0.000 description 1
• 150000003333 secondary alcohols Chemical class 0.000 description 1
• 238000013207 serial dilution Methods 0.000 description 1
• 238000010898 silica gel chromatography Methods 0.000 description 1
• 239000000377 silicon dioxide Substances 0.000 description 1
• 239000002002 slurry Substances 0.000 description 1
• 239000007974 sodium acetate buffer Substances 0.000 description 1
• BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
• 235000009518 sodium iodide Nutrition 0.000 description 1
• 239000008247 solid mixture Substances 0.000 description 1
• 241000894007 species Species 0.000 description 1
• 230000009870 specific binding Effects 0.000 description 1
• 238000001228 spectrum Methods 0.000 description 1
• 239000007921 spray Substances 0.000 description 1
• 239000008107 starch Substances 0.000 description 1
• 235000019698 starch Nutrition 0.000 description 1
• 239000008223 sterile water Substances 0.000 description 1
• 230000001954 sterilising effect Effects 0.000 description 1
• 238000007920 subcutaneous administration Methods 0.000 description 1
• 239000005720 sucrose Substances 0.000 description 1
• 238000006277 sulfonation reaction Methods 0.000 description 1
• 150000003457 sulfones Chemical class 0.000 description 1
• 150000003463 sulfur Chemical class 0.000 description 1
• 125000004354 sulfur functional group Chemical group 0.000 description 1
• HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
• 239000000375 suspending agent Substances 0.000 description 1
• 238000010189 synthetic method Methods 0.000 description 1
• 235000020357 syrup Nutrition 0.000 description 1
• 239000006188 syrup Substances 0.000 description 1
• 239000000454 talc Substances 0.000 description 1
• 229910052623 talc Inorganic materials 0.000 description 1
• 235000012222 talc Nutrition 0.000 description 1
• 238000012360 testing method Methods 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1
• 125000001544 thienyl group Chemical group 0.000 description 1
• 150000003568 thioethers Chemical class 0.000 description 1
• 231100000331 toxic Toxicity 0.000 description 1
• 230000002588 toxic effect Effects 0.000 description 1
• 239000000196 tragacanth Substances 0.000 description 1
• 235000010487 tragacanth Nutrition 0.000 description 1
• 229940116362 tragacanth Drugs 0.000 description 1
• YIYBQIKDCADOSF-ONEGZZNKSA-N trans-pent-2-enoic acid Chemical compound CC\C=C\C(O)=O YIYBQIKDCADOSF-ONEGZZNKSA-N 0.000 description 1
• 238000013518 transcription Methods 0.000 description 1
• 230000035897 transcription Effects 0.000 description 1
• JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
• JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
• LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
• 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
• FUCBQMFTYFQCOB-UHFFFAOYSA-N trityl perchlorate Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(OCl(=O)(=O)=O)C1=CC=CC=C1 FUCBQMFTYFQCOB-UHFFFAOYSA-N 0.000 description 1
• HFTAFOQKODTIJY-UHFFFAOYSA-N umbelliferone Natural products Cc1cc2C=CC(=O)Oc2cc1OCC=CC(C)(C)O HFTAFOQKODTIJY-UHFFFAOYSA-N 0.000 description 1
• 241001430294 unidentified retrovirus Species 0.000 description 1
• 235000015112 vegetable and seed oil Nutrition 0.000 description 1
• 239000008158 vegetable oil Substances 0.000 description 1
• 229920002554 vinyl polymer Polymers 0.000 description 1
• UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
• 238000005406 washing Methods 0.000 description 1