NO315747B1 - Pyronderivater, anvendelse derav, samt farmasöytisk preparat - Google Patents
Pyronderivater, anvendelse derav, samt farmasöytisk preparat Download PDFInfo
- Publication number
- NO315747B1 NO315747B1 NO19962016A NO962016A NO315747B1 NO 315747 B1 NO315747 B1 NO 315747B1 NO 19962016 A NO19962016 A NO 19962016A NO 962016 A NO962016 A NO 962016A NO 315747 B1 NO315747 B1 NO 315747B1
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy
- pyran
- phenyl
- mmol
- thio
- Prior art date
Links
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical class O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 8
- 238000011282 treatment Methods 0.000 claims abstract description 17
- 201000010099 disease Diseases 0.000 claims abstract description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 257
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 171
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 91
- -1 cyclohexylthio Chemical group 0.000 claims description 80
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 31
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 29
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 26
- 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 23
- 208000015181 infectious disease Diseases 0.000 claims description 14
- 241001430294 unidentified retrovirus Species 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- FPXCTCSPJUAVAK-UHFFFAOYSA-N 4-hydroxy-3-[(2-methoxyphenyl)sulfanyl-phenylmethyl]-6-phenylpyran-2-one Chemical compound COC1=CC=CC=C1SC(C=1C(OC(=CC=1O)C=1C=CC=CC=1)=O)C1=CC=CC=C1 FPXCTCSPJUAVAK-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
- YDVLLGQTSWYWAN-UHFFFAOYSA-N 3-(2-cyclohexyl-1-phenylsulfanylethyl)-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(SC=1C=CC=CC=1)CC1CCCCC1 YDVLLGQTSWYWAN-UHFFFAOYSA-N 0.000 claims description 3
- ATEQLMBUVMOQAP-UHFFFAOYSA-N 3-[1,4-bis(phenylsulfanyl)butyl]-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(SC=1C=CC=CC=1)CCCSC1=CC=CC=C1 ATEQLMBUVMOQAP-UHFFFAOYSA-N 0.000 claims description 3
- ALLQSRTWINEASI-UHFFFAOYSA-N 3-[cyclohexylsulfanyl(phenyl)methyl]-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(C=1C=CC=CC=1)SC1CCCCC1 ALLQSRTWINEASI-UHFFFAOYSA-N 0.000 claims description 3
- XFVAZZZKQWGAJJ-UHFFFAOYSA-N 4-hydroxy-3-(3-methyl-1-phenylsulfanylbutyl)-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(CC(C)C)SC1=CC=CC=C1 XFVAZZZKQWGAJJ-UHFFFAOYSA-N 0.000 claims description 3
- NSNQHVUFIHOOEN-UHFFFAOYSA-N 4-hydroxy-3-[naphthalen-2-yl(phenylsulfanyl)methyl]-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(C=1C=C2C=CC=CC2=CC=1)SC1=CC=CC=C1 NSNQHVUFIHOOEN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- PIVCSFQAABPVOR-UHFFFAOYSA-N 3-(1-benzylsulfanyl-3-methylbutyl)-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(CC(C)C)SCC1=CC=CC=C1 PIVCSFQAABPVOR-UHFFFAOYSA-N 0.000 claims description 2
- HIJDADBORWRDJP-UHFFFAOYSA-N 3-(1-cyclopentylsulfanyl-3-methylbutyl)-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(CC(C)C)SC1CCCC1 HIJDADBORWRDJP-UHFFFAOYSA-N 0.000 claims description 2
- CPJFBIJMFGBOEE-UHFFFAOYSA-N 3-[1-(2,6-dimethylphenyl)sulfanyl-3-methylbutyl]-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(CC(C)C)SC1=C(C)C=CC=C1C CPJFBIJMFGBOEE-UHFFFAOYSA-N 0.000 claims description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims description 2
- UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 claims description 2
- OJWIIEFLUZBLJI-UHFFFAOYSA-N 4-hydroxy-3-(4-methyl-1-phenylsulfanylpentyl)-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(CCC(C)C)SC1=CC=CC=C1 OJWIIEFLUZBLJI-UHFFFAOYSA-N 0.000 claims description 2
- GAOWSYDKRZMCRK-UHFFFAOYSA-N 4-hydroxy-3-[2-(2-methylpropyl)-5-propan-2-ylphenyl]-6-(1-phenylbutan-2-yl)pyran-2-one Chemical compound C=1C(O)=C(C=2C(=CC=C(C=2)C(C)C)CC(C)C)C(=O)OC=1C(CC)CC1=CC=CC=C1 GAOWSYDKRZMCRK-UHFFFAOYSA-N 0.000 claims description 2
- AROIBMDJLHDALJ-UHFFFAOYSA-N 4-hydroxy-3-[naphthalen-2-ylsulfanyl(phenyl)methyl]-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(SC=1C=C2C=CC=CC2=CC=1)C1=CC=CC=C1 AROIBMDJLHDALJ-UHFFFAOYSA-N 0.000 claims description 2
- MTOIXHALBDUYDN-UHFFFAOYSA-N 6-(1-benzylcyclopentyl)-3-(1-cyclopentylsulfanyl-2-cyclopropylethyl)-4-hydroxypyran-2-one Chemical compound OC=1C=C(C2(CC=3C=CC=CC=3)CCCC2)OC(=O)C=1C(SC1CCCC1)CC1CC1 MTOIXHALBDUYDN-UHFFFAOYSA-N 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003944 tolyl group Chemical group 0.000 claims description 2
- OTCMMFBVHHZEEP-UHFFFAOYSA-N 3-[cyclopropyl(phenyl)methyl]-4-hydroxy-6-(2-methyl-4-phenylbutan-2-yl)pyran-2-one Chemical compound C=1C(O)=C(C(C2CC2)C=2C=CC=CC=2)C(=O)OC=1C(C)(C)CCC1=CC=CC=C1 OTCMMFBVHHZEEP-UHFFFAOYSA-N 0.000 claims 2
- SCTKFBQNFHKDHF-UHFFFAOYSA-N 3-(1-benzylsulfanyl-2-phenylethyl)-6-(3,5-dimethylphenyl)-4-hydroxy-5-methylpyran-2-one Chemical compound CC1=CC(C)=CC(C2=C(C(O)=C(C(CC=3C=CC=CC=3)SCC=3C=CC=CC=3)C(=O)O2)C)=C1 SCTKFBQNFHKDHF-UHFFFAOYSA-N 0.000 claims 1
- MEENRHDFKDUKNO-UHFFFAOYSA-N 3-[1-(2,6-dichlorophenyl)sulfanyl-3-methylbutyl]-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(CC(C)C)SC1=C(Cl)C=CC=C1Cl MEENRHDFKDUKNO-UHFFFAOYSA-N 0.000 claims 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
- NZTFQRJTZJIFIZ-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-2-oxo-6-[1-(2-phenylethyl)cyclopropyl]pyran-3-yl]methyl]phenyl]benzenesulfonamide Chemical compound OC=1C=C(C2(CCC=3C=CC=CC=3)CC2)OC(=O)C=1C(C=1C=C(NS(=O)(=O)C=2C=CC=CC=2)C=CC=1)C1CC1 NZTFQRJTZJIFIZ-UHFFFAOYSA-N 0.000 claims 1
- DCJKTFCKODMECI-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-6-(2-methyl-1-phenylpropan-2-yl)-2-oxopyran-3-yl]methyl]phenyl]benzenesulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3C=CC=CC=3)C=CC=2)C(=O)OC=1C(C)(C)CC1=CC=CC=C1 DCJKTFCKODMECI-UHFFFAOYSA-N 0.000 claims 1
- COACFJNRRRDMBD-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-6-(2-methyl-4-phenylbutan-2-yl)-2-oxopyran-3-yl]methyl]phenyl]benzenesulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3C=CC=CC=3)C=CC=2)C(=O)OC=1C(C)(C)CCC1=CC=CC=C1 COACFJNRRRDMBD-UHFFFAOYSA-N 0.000 claims 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000004014 thioethyl group Chemical group [H]SC([H])([H])C([H])([H])* 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 228
- 238000003786 synthesis reaction Methods 0.000 abstract description 12
- 208000030507 AIDS Diseases 0.000 abstract description 11
- 108010017640 Aspartic Acid Proteases Proteins 0.000 abstract description 10
- 102000004580 Aspartic Acid Proteases Human genes 0.000 abstract description 10
- 230000015572 biosynthetic process Effects 0.000 abstract description 10
- 238000011161 development Methods 0.000 abstract description 5
- 238000002560 therapeutic procedure Methods 0.000 abstract description 2
- 208000035143 Bacterial infection Diseases 0.000 abstract 1
- 208000036142 Viral infection Diseases 0.000 abstract 1
- 230000001580 bacterial effect Effects 0.000 abstract 1
- 208000022362 bacterial infectious disease Diseases 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- 230000009385 viral infection Effects 0.000 abstract 1
- 238000005481 NMR spectroscopy Methods 0.000 description 238
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 207
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 186
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 168
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 168
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 145
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 136
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 110
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 98
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 87
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 74
- 235000019441 ethanol Nutrition 0.000 description 71
- UWCSWBPHENSQNW-UHFFFAOYSA-N 4-hydroxy-6-phenylpyran-2-one Chemical compound O1C(=O)C=C(O)C=C1C1=CC=CC=C1 UWCSWBPHENSQNW-UHFFFAOYSA-N 0.000 description 59
- 239000000203 mixture Substances 0.000 description 57
- 239000000243 solution Substances 0.000 description 50
- 238000006243 chemical reaction Methods 0.000 description 46
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 description 43
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 40
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000002904 solvent Substances 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
- 238000002360 preparation method Methods 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 24
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 24
- GYIROBLMPMMTDW-UHFFFAOYSA-N 2-(2-phenylethylsulfanyl)propanedioic acid Chemical compound OC(=O)C(C(O)=O)SCCC1=CC=CC=C1 GYIROBLMPMMTDW-UHFFFAOYSA-N 0.000 description 23
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 22
- AFFPCIMDERUIST-UHFFFAOYSA-N trimethyl(1-phenylethenoxy)silane Chemical group C[Si](C)(C)OC(=C)C1=CC=CC=C1 AFFPCIMDERUIST-UHFFFAOYSA-N 0.000 description 20
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 18
- QLGGACCGGOJMBU-UHFFFAOYSA-N 2-benzylsulfanylpropanedioic acid Chemical compound OC(=O)C(C(O)=O)SCC1=CC=CC=C1 QLGGACCGGOJMBU-UHFFFAOYSA-N 0.000 description 16
- 241000725303 Human immunodeficiency virus Species 0.000 description 16
- 239000002253 acid Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 15
- 239000012043 crude product Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- BANQLUBZRNPZTE-UHFFFAOYSA-N 2-(2-propan-2-ylphenyl)sulfanylpropanedioic acid Chemical compound CC(C)C1=CC=CC=C1SC(C(O)=O)C(O)=O BANQLUBZRNPZTE-UHFFFAOYSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 239000003112 inhibitor Substances 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 13
- 238000004458 analytical method Methods 0.000 description 13
- VFUUZMHGSHQCCD-UHFFFAOYSA-N diethyl 2-(2-phenylethylsulfanyl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)SCCC1=CC=CC=C1 VFUUZMHGSHQCCD-UHFFFAOYSA-N 0.000 description 13
- HCPOCMMGKBZWSJ-UHFFFAOYSA-N ethyl 3-hydrazinyl-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)NN HCPOCMMGKBZWSJ-UHFFFAOYSA-N 0.000 description 13
- 238000001704 evaporation Methods 0.000 description 13
- 230000008020 evaporation Effects 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- 229910000104 sodium hydride Inorganic materials 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 239000012312 sodium hydride Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 238000009835 boiling Methods 0.000 description 10
- 238000004440 column chromatography Methods 0.000 description 10
- CMKBCTPCXZNQKX-UHFFFAOYSA-N cyclohexanethiol Chemical compound SC1CCCCC1 CMKBCTPCXZNQKX-UHFFFAOYSA-N 0.000 description 10
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 10
- 229920006395 saturated elastomer Polymers 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 9
- 239000003480 eluent Substances 0.000 description 9
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 9
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 8
- 102000035195 Peptidases Human genes 0.000 description 8
- 108091005804 Peptidases Proteins 0.000 description 8
- 239000004365 Protease Substances 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 241000700605 Viruses Species 0.000 description 8
- 239000000872 buffer Substances 0.000 description 8
- 238000009833 condensation Methods 0.000 description 8
- 230000005494 condensation Effects 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 229910052744 lithium Inorganic materials 0.000 description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- DECDYYNGJXKAAC-UHFFFAOYSA-N 3-amino-4-hydroxy-6-phenylpyran-2-one;hydrochloride Chemical compound Cl.O1C(=O)C(N)=C(O)C=C1C1=CC=CC=C1 DECDYYNGJXKAAC-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 102000004190 Enzymes Human genes 0.000 description 7
- 108090000790 Enzymes Proteins 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- SSBBQNOCGGHKJQ-UHFFFAOYSA-N hydroxy-(4-methylphenyl)-oxo-sulfanylidene-$l^{6}-sulfane Chemical class CC1=CC=C(S(S)(=O)=O)C=C1 SSBBQNOCGGHKJQ-UHFFFAOYSA-N 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000003085 diluting agent Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 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 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 230000000840 anti-viral effect Effects 0.000 description 5
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 238000011835 investigation Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 4
- LUJMEECXHPYQOF-UHFFFAOYSA-N 3-hydroxyacetophenone Chemical compound CC(=O)C1=CC=CC(O)=C1 LUJMEECXHPYQOF-UHFFFAOYSA-N 0.000 description 4
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 4
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- WVDYBOADDMMFIY-UHFFFAOYSA-N Cyclopentanethiol Chemical compound SC1CCCC1 WVDYBOADDMMFIY-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 230000002354 daily effect Effects 0.000 description 4
- GPIBPZVSHZQSLA-UHFFFAOYSA-N diethyl 2-benzylsulfanylpropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)SCC1=CC=CC=C1 GPIBPZVSHZQSLA-UHFFFAOYSA-N 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- FDZPQUUHLRJKJL-UHFFFAOYSA-N (4-methylphenyl)-oxo-(2-phenylethoxy)-sulfanylidene-$l^{6}-sulfane Chemical compound C1=CC(C)=CC=C1S(=O)(=S)OCCC1=CC=CC=C1 FDZPQUUHLRJKJL-UHFFFAOYSA-N 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 3
- AJJKPRWJTNUWLU-UHFFFAOYSA-N 3-aminopyran-2-one Chemical class NC1=CC=COC1=O AJJKPRWJTNUWLU-UHFFFAOYSA-N 0.000 description 3
- XMUFTXBOUZFFSP-UHFFFAOYSA-N 6-(3-chlorophenyl)-4-hydroxypyran-2-one Chemical compound O1C(=O)C=C(O)C=C1C1=CC=CC(Cl)=C1 XMUFTXBOUZFFSP-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- IYXGSMUGOJNHAZ-UHFFFAOYSA-N Ethyl malonate Chemical compound CCOC(=O)CC(=O)OCC IYXGSMUGOJNHAZ-UHFFFAOYSA-N 0.000 description 3
- 208000031886 HIV Infections Diseases 0.000 description 3
- 108010010369 HIV Protease Proteins 0.000 description 3
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 108010076039 Polyproteins Proteins 0.000 description 3
- KOOADCGQJDGAGA-UHFFFAOYSA-N [amino(dimethyl)silyl]methane Chemical compound C[Si](C)(C)N KOOADCGQJDGAGA-UHFFFAOYSA-N 0.000 description 3
- 230000036436 anti-hiv Effects 0.000 description 3
- 239000003443 antiviral agent Substances 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- QWLWTXHDWKWZFB-UHFFFAOYSA-N diethyl 2-thiophen-2-ylpropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)C1=CC=CS1 QWLWTXHDWKWZFB-UHFFFAOYSA-N 0.000 description 3
- JUCFDDLYEFBUPE-UHFFFAOYSA-N ethyl 2-[4-[4-hydroxy-6-oxo-5-(2-phenylethylsulfanyl)pyran-2-yl]phenoxy]acetate Chemical compound C1=CC(OCC(=O)OCC)=CC=C1C(OC1=O)=CC(O)=C1SCCC1=CC=CC=C1 JUCFDDLYEFBUPE-UHFFFAOYSA-N 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- FSPSELPMWGWDRY-UHFFFAOYSA-N m-Methylacetophenone Chemical compound CC(=O)C1=CC=CC(C)=C1 FSPSELPMWGWDRY-UHFFFAOYSA-N 0.000 description 3
- 230000010534 mechanism of action Effects 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 3
- SXYFKXOFMCIXQW-UHFFFAOYSA-N propanedioyl dichloride Chemical compound ClC(=O)CC(Cl)=O SXYFKXOFMCIXQW-UHFFFAOYSA-N 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 230000001177 retroviral effect Effects 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- 230000003612 virological effect Effects 0.000 description 3
- 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 3
- WNWSZVFXBFEPJH-UHFFFAOYSA-N (4-methylphenyl)-oxo-(4-phenylbutoxy)-sulfanylidene-$l^{6}-sulfane Chemical compound C1=CC(C)=CC=C1S(=O)(=S)OCCCCC1=CC=CC=C1 WNWSZVFXBFEPJH-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XSYFMAXTDDQGHN-UHFFFAOYSA-N 1-(1,4-benzodioxin-6-yl)ethanone Chemical compound O1C=COC2=CC(C(=O)C)=CC=C21 XSYFMAXTDDQGHN-UHFFFAOYSA-N 0.000 description 2
- BKIHFZLJJUNKMZ-UHFFFAOYSA-N 1-(3,5-dimethylphenyl)ethanone Chemical compound CC(=O)C1=CC(C)=CC(C)=C1 BKIHFZLJJUNKMZ-UHFFFAOYSA-N 0.000 description 2
- UUWJBXKHMMQDED-UHFFFAOYSA-N 1-(3-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(Cl)=C1 UUWJBXKHMMQDED-UHFFFAOYSA-N 0.000 description 2
- HRUAWSQBQLYDKH-UHFFFAOYSA-N 1-(3-methoxy-4-phenylmethoxyphenyl)ethanone Chemical compound COC1=CC(C(C)=O)=CC=C1OCC1=CC=CC=C1 HRUAWSQBQLYDKH-UHFFFAOYSA-N 0.000 description 2
- FGQMEAWGAUALJQ-UHFFFAOYSA-N 1-(3-phenylmethoxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(OCC=2C=CC=CC=2)=C1 FGQMEAWGAUALJQ-UHFFFAOYSA-N 0.000 description 2
- MKYMYZJJFMPDOA-UHFFFAOYSA-N 1-(4-phenylmethoxyphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCC1=CC=CC=C1 MKYMYZJJFMPDOA-UHFFFAOYSA-N 0.000 description 2
- DWFKUFJMJVKGES-UHFFFAOYSA-N 1-[4-(pyridin-3-ylmethoxy)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCC1=CC=CN=C1 DWFKUFJMJVKGES-UHFFFAOYSA-N 0.000 description 2
- ZIUQRABHZNPKSO-UHFFFAOYSA-N 2-(2-methoxyphenyl)ethoxy-(4-methylphenyl)-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound COC1=CC=CC=C1CCOS(=O)(=S)C1=CC=C(C)C=C1 ZIUQRABHZNPKSO-UHFFFAOYSA-N 0.000 description 2
- DSCJETUEDFKYGN-UHFFFAOYSA-N 2-Methoxybenzenethiol Chemical compound COC1=CC=CC=C1S DSCJETUEDFKYGN-UHFFFAOYSA-N 0.000 description 2
- NTJYRKCCICRIER-UHFFFAOYSA-N 2-[2-(cyclopropylmethyl)phenyl]sulfanylpropanedioic acid Chemical compound OC(=O)C(C(O)=O)SC1=CC=CC=C1CC1CC1 NTJYRKCCICRIER-UHFFFAOYSA-N 0.000 description 2
- XSAYZAUNJMRRIR-UHFFFAOYSA-N 2-acetylnaphthalene Chemical compound C1=CC=CC2=CC(C(=O)C)=CC=C21 XSAYZAUNJMRRIR-UHFFFAOYSA-N 0.000 description 2
- JJMDTERTPNYIGZ-UHFFFAOYSA-N 2-cyclohexylacetaldehyde Chemical compound O=CCC1CCCCC1 JJMDTERTPNYIGZ-UHFFFAOYSA-N 0.000 description 2
- PJKVFARRVXDXAD-UHFFFAOYSA-N 2-naphthaldehyde Chemical compound C1=CC=CC2=CC(C=O)=CC=C21 PJKVFARRVXDXAD-UHFFFAOYSA-N 0.000 description 2
- MVNWYJXNGVGPER-UHFFFAOYSA-N 3-(1-cyclohexylsulfanyl-3-methylbutyl)-6-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-hydroxypyran-2-one Chemical compound OC=1C=C(C=2C=C3OCCOC3=CC=2)OC(=O)C=1C(CC(C)C)SC1CCCCC1 MVNWYJXNGVGPER-UHFFFAOYSA-N 0.000 description 2
- WEGYGNROSJDEIW-UHFFFAOYSA-N 3-Acetylpyridine Chemical compound CC(=O)C1=CC=CN=C1 WEGYGNROSJDEIW-UHFFFAOYSA-N 0.000 description 2
- KXQAQVRISJETLZ-UHFFFAOYSA-N 3-[(4-hydroxy-2-oxo-6-phenylpyran-3-yl)sulfanylmethyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(CSC=2C(OC(=CC=2O)C=2C=CC=CC=2)=O)=C1 KXQAQVRISJETLZ-UHFFFAOYSA-N 0.000 description 2
- QSFOQTCPGNVRSL-UHFFFAOYSA-N 3-[benzylsulfanyl(phenyl)methyl]-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(C=1C=CC=CC=1)SCC1=CC=CC=C1 QSFOQTCPGNVRSL-UHFFFAOYSA-N 0.000 description 2
- QDXWWEZZGVALSV-UHFFFAOYSA-N 3-benzylsulfanyl-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1SCC1=CC=CC=C1 QDXWWEZZGVALSV-UHFFFAOYSA-N 0.000 description 2
- LSZQTPAJTFASCD-UHFFFAOYSA-N 4-hydroxy-3-(naphthalen-2-ylmethylsulfanyl)-6-phenylpyran-2-one Chemical compound O1C(=O)C(SCC=2C=C3C=CC=CC3=CC=2)=C(O)C=C1C1=CC=CC=C1 LSZQTPAJTFASCD-UHFFFAOYSA-N 0.000 description 2
- HAPIWDDWRKVILV-UHFFFAOYSA-N 4-hydroxy-3-phenacylsulfanyl-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1SCC(=O)C1=CC=CC=C1 HAPIWDDWRKVILV-UHFFFAOYSA-N 0.000 description 2
- NNMBWFBLHKMVSF-UHFFFAOYSA-N 4-hydroxy-6-(4-hydroxyphenyl)-3-(2-phenylethylsulfanyl)pyran-2-one Chemical compound C1=CC(O)=CC=C1C(OC1=O)=CC(O)=C1SCCC1=CC=CC=C1 NNMBWFBLHKMVSF-UHFFFAOYSA-N 0.000 description 2
- VXIXUWQIVKSKSA-UHFFFAOYSA-N 4-hydroxycoumarin Chemical compound C1=CC=CC2=C1OC(=O)C=C2O VXIXUWQIVKSKSA-UHFFFAOYSA-N 0.000 description 2
- VNZOLPIHDIJPBZ-UHFFFAOYSA-N 4-hydroxypyran-2-one Chemical class OC=1C=COC(=O)C=1 VNZOLPIHDIJPBZ-UHFFFAOYSA-N 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- SYVWSLSKIGFIOO-UHFFFAOYSA-N 6-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-hydroxypyran-2-one Chemical compound O1C(=O)C=C(O)C=C1C1=CC=C(OCCO2)C2=C1 SYVWSLSKIGFIOO-UHFFFAOYSA-N 0.000 description 2
- HBGJRQFNWNBQOR-UHFFFAOYSA-N 6-(4-chlorophenyl)-4-hydroxypyran-2-one Chemical compound O1C(=O)C=C(O)C=C1C1=CC=C(Cl)C=C1 HBGJRQFNWNBQOR-UHFFFAOYSA-N 0.000 description 2
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- 108010078851 HIV Reverse Transcriptase Proteins 0.000 description 2
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 2
- 108010016183 Human immunodeficiency virus 1 p16 protease Proteins 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229940110456 cocoa butter Drugs 0.000 description 2
- 235000019868 cocoa butter Nutrition 0.000 description 2
- 150000004775 coumarins Chemical class 0.000 description 2
- KVFDZFBHBWTVID-UHFFFAOYSA-N cyclohexanecarbaldehyde Chemical compound O=CC1CCCCC1 KVFDZFBHBWTVID-UHFFFAOYSA-N 0.000 description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 230000005595 deprotonation Effects 0.000 description 2
- 238000010537 deprotonation reaction Methods 0.000 description 2
- BAJDKXVKHBKNNC-UHFFFAOYSA-N diethyl 2-(2-propan-2-ylphenyl)sulfanylpropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)SC1=CC=CC=C1C(C)C BAJDKXVKHBKNNC-UHFFFAOYSA-N 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- DWQYETJWKMRRCP-UHFFFAOYSA-N ethyl 4-[4-hydroxy-6-oxo-5-(2-phenylethylsulfanyl)pyran-2-yl]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1C(OC1=O)=CC(O)=C1SCCC1=CC=CC=C1 DWQYETJWKMRRCP-UHFFFAOYSA-N 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 150000002391 heterocyclic compounds Chemical class 0.000 description 2
- 239000004030 hiv protease inhibitor Substances 0.000 description 2
- 239000008240 homogeneous mixture Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000002458 infectious effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000002576 ketones Chemical class 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
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- NHFXFWUOYKCKBC-UHFFFAOYSA-N methoxy-(4-methylphenyl)-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound COS(=O)(=S)C1=CC=C(C)C=C1 NHFXFWUOYKCKBC-UHFFFAOYSA-N 0.000 description 2
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- XNLBCXGRQWUJLU-UHFFFAOYSA-N naphthalene-2-carbonyl chloride Chemical compound C1=CC=CC2=CC(C(=O)Cl)=CC=C21 XNLBCXGRQWUJLU-UHFFFAOYSA-N 0.000 description 2
- 238000006396 nitration reaction Methods 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 208000011580 syndromic disease Diseases 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- ICYJNBKAYPZIHE-UHFFFAOYSA-N thiopyran-2-one Chemical class O=C1C=CC=CS1 ICYJNBKAYPZIHE-UHFFFAOYSA-N 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 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
- 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 2
- 239000011345 viscous material Substances 0.000 description 2
- 229960005080 warfarin Drugs 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- QLXLDNPWHIBBJK-UHFFFAOYSA-N (2,6-dimethylphenyl)methoxy-(4-methylphenyl)-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound C1=CC(C)=CC=C1S(=O)(=S)OCC1=C(C)C=CC=C1C QLXLDNPWHIBBJK-UHFFFAOYSA-N 0.000 description 1
- DCDZGGSHIMUDMR-UHFFFAOYSA-N (2-methoxyphenyl)methoxy-(4-methylphenyl)-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound COC1=CC=CC=C1COS(=O)(=S)C1=CC=C(C)C=C1 DCDZGGSHIMUDMR-UHFFFAOYSA-N 0.000 description 1
- MGZOXZPZHVOXQB-UHFFFAOYSA-N (2-oxochromen-7-yl) acetate Chemical compound C1=CC(=O)OC2=CC(OC(=O)C)=CC=C21 MGZOXZPZHVOXQB-UHFFFAOYSA-N 0.000 description 1
- FMCAFXHLMUOIGG-JTJHWIPRSA-N (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-JTJHWIPRSA-N 0.000 description 1
- SKQHYBKHTJTTJI-UHFFFAOYSA-N (3-methoxyphenyl)methoxy-(4-methylphenyl)-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound COC1=CC=CC(COS(=O)(=S)C=2C=CC(C)=CC=2)=C1 SKQHYBKHTJTTJI-UHFFFAOYSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- HFHIRXFGKJJNIT-UHFFFAOYSA-N (4-acetylphenyl) benzoate Chemical compound C1=CC(C(=O)C)=CC=C1OC(=O)C1=CC=CC=C1 HFHIRXFGKJJNIT-UHFFFAOYSA-N 0.000 description 1
- LGIYQRDUJSCGHD-UHFFFAOYSA-N (4-methoxyphenyl)methoxy-(4-methylphenyl)-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound C1=CC(OC)=CC=C1COS(=O)(=S)C1=CC=C(C)C=C1 LGIYQRDUJSCGHD-UHFFFAOYSA-N 0.000 description 1
- CNXJDYSPZOTBHS-UHFFFAOYSA-N (4-methylphenyl)-[(3-methylphenyl)methoxy]-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound C1=CC(C)=CC=C1S(=O)(=S)OCC1=CC=CC(C)=C1 CNXJDYSPZOTBHS-UHFFFAOYSA-N 0.000 description 1
- GMSPBQAFPQWFSF-UHFFFAOYSA-N (4-methylphenyl)-oxo-(2-phenoxyethoxy)-sulfanylidene-$l^{6}-sulfane Chemical compound C1=CC(C)=CC=C1S(=O)(=S)OCCOC1=CC=CC=C1 GMSPBQAFPQWFSF-UHFFFAOYSA-N 0.000 description 1
- IHLDZOQPJNRBQR-UHFFFAOYSA-N (4-methylphenyl)-oxo-[(3-phenoxyphenyl)methoxy]-sulfanylidene-$l^{6}-sulfane Chemical compound C1=CC(C)=CC=C1S(=O)(=S)OCC1=CC=CC(OC=2C=CC=CC=2)=C1 IHLDZOQPJNRBQR-UHFFFAOYSA-N 0.000 description 1
- SEMAOAZUCZFLMZ-UHFFFAOYSA-N (4-methylphenyl)-oxo-[(4-phenylmethoxyphenyl)methoxy]-sulfanylidene-$l^{6}-sulfane Chemical compound C1=CC(C)=CC=C1S(=O)(=S)OCC(C=C1)=CC=C1OCC1=CC=CC=C1 SEMAOAZUCZFLMZ-UHFFFAOYSA-N 0.000 description 1
- ZGYIXVSQHOKQRZ-COIATFDQSA-N (e)-n-[4-[3-chloro-4-(pyridin-2-ylmethoxy)anilino]-3-cyano-7-[(3s)-oxolan-3-yl]oxyquinolin-6-yl]-4-(dimethylamino)but-2-enamide Chemical compound N#CC1=CN=C2C=C(O[C@@H]3COCC3)C(NC(=O)/C=C/CN(C)C)=CC2=C1NC(C=C1Cl)=CC=C1OCC1=CC=CC=N1 ZGYIXVSQHOKQRZ-COIATFDQSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
- DDXBCZCBZGPSHD-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)ethanone Chemical compound CC(=O)C1=C(C)C=CC=C1C DDXBCZCBZGPSHD-UHFFFAOYSA-N 0.000 description 1
- FLQWILGTHKHWNV-UHFFFAOYSA-N 1-(2,6-dimethylpyridin-4-yl)ethanone Chemical compound CC(=O)C1=CC(C)=NC(C)=C1 FLQWILGTHKHWNV-UHFFFAOYSA-N 0.000 description 1
- ZDOYHCIRUPHUHN-UHFFFAOYSA-N 1-(2-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1Cl ZDOYHCIRUPHUHN-UHFFFAOYSA-N 0.000 description 1
- JGMBBKVZFUHCJC-UHFFFAOYSA-N 1-(3,5-dichlorophenyl)ethanone Chemical compound CC(=O)C1=CC(Cl)=CC(Cl)=C1 JGMBBKVZFUHCJC-UHFFFAOYSA-N 0.000 description 1
- QILWOKAXHOAFOF-UHFFFAOYSA-N 1-(3-chloro-4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1Cl QILWOKAXHOAFOF-UHFFFAOYSA-N 0.000 description 1
- BAYUSCHCCGXLAY-UHFFFAOYSA-N 1-(3-methoxyphenyl)ethanone Chemical compound COC1=CC=CC(C(C)=O)=C1 BAYUSCHCCGXLAY-UHFFFAOYSA-N 0.000 description 1
- FZCDBGYCFVKRDV-UHFFFAOYSA-N 1-(3-phenoxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 FZCDBGYCFVKRDV-UHFFFAOYSA-N 0.000 description 1
- HUHQPWCDGRZWMH-UHFFFAOYSA-N 1-(3-phenylphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1 HUHQPWCDGRZWMH-UHFFFAOYSA-N 0.000 description 1
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
- QCZZSANNLWPGEA-UHFFFAOYSA-N 1-(4-phenylphenyl)ethanone Chemical group C1=CC(C(=O)C)=CC=C1C1=CC=CC=C1 QCZZSANNLWPGEA-UHFFFAOYSA-N 0.000 description 1
- XUDYHODVSUXRPW-UHFFFAOYSA-N 1-(4-phenylsulfanylphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1SC1=CC=CC=C1 XUDYHODVSUXRPW-UHFFFAOYSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- ODKVILSECODRIT-UHFFFAOYSA-N 1-[3-(2-phenylethoxy)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(OCCC=2C=CC=CC=2)=C1 ODKVILSECODRIT-UHFFFAOYSA-N 0.000 description 1
- UYHTUQHYGKAYJM-UHFFFAOYSA-N 1-[3-(trifluoromethoxy)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(OC(F)(F)F)=C1 UYHTUQHYGKAYJM-UHFFFAOYSA-N 0.000 description 1
- FOMSTKPBNYIWRM-UHFFFAOYSA-N 1-[4-(2-morpholin-4-ylethoxy)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCCN1CCOCC1 FOMSTKPBNYIWRM-UHFFFAOYSA-N 0.000 description 1
- WKAZTGOEVXZSBE-UHFFFAOYSA-N 1-[4-(2-phenylethoxy)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCCC1=CC=CC=C1 WKAZTGOEVXZSBE-UHFFFAOYSA-N 0.000 description 1
- KIRXEYNVGWVPRO-UHFFFAOYSA-N 1-[4-(2-phenylethyl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1CCC1=CC=CC=C1 KIRXEYNVGWVPRO-UHFFFAOYSA-N 0.000 description 1
- NDURMRZBGXFIPU-UHFFFAOYSA-N 1-[4-(3,5-dimethyl-1,2-oxazol-4-yl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1C1=C(C)ON=C1C NDURMRZBGXFIPU-UHFFFAOYSA-N 0.000 description 1
- RYWVBYIATDKGDH-UHFFFAOYSA-N 1-[4-(3-phenylpropoxy)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCCCC1=CC=CC=C1 RYWVBYIATDKGDH-UHFFFAOYSA-N 0.000 description 1
- FGFHDNIGKVTTLC-UHFFFAOYSA-N 1-[4-(benzenesulfonyl)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)C1=CC=CC=C1 FGFHDNIGKVTTLC-UHFFFAOYSA-N 0.000 description 1
- WHFLXHLZDHBALK-UHFFFAOYSA-N 1-[4-(cyclohexylmethoxy)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCC1CCCCC1 WHFLXHLZDHBALK-UHFFFAOYSA-N 0.000 description 1
- ABDXJHZEEBMOKS-UHFFFAOYSA-N 1-[4-(pyridin-2-ylmethoxy)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCC1=CC=CC=N1 ABDXJHZEEBMOKS-UHFFFAOYSA-N 0.000 description 1
- UPVQLTNPUSGLSS-UHFFFAOYSA-N 1-[4-(pyridin-4-ylmethoxy)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCC1=CC=NC=C1 UPVQLTNPUSGLSS-UHFFFAOYSA-N 0.000 description 1
- FYNMAPJTGKYTHR-UHFFFAOYSA-N 1-bromo-1-methylcyclopropane Chemical compound CC1(Br)CC1 FYNMAPJTGKYTHR-UHFFFAOYSA-N 0.000 description 1
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 1
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 description 1
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- WMQUKDQWMMOHSA-UHFFFAOYSA-N 1-pyridin-4-ylethanone Chemical compound CC(=O)C1=CC=NC=C1 WMQUKDQWMMOHSA-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YXWWHNCQZBVZPV-UHFFFAOYSA-N 2'-methylacetophenone Chemical compound CC(=O)C1=CC=CC=C1C YXWWHNCQZBVZPV-UHFFFAOYSA-N 0.000 description 1
- JBISHCXLCGVPGW-UHFFFAOYSA-N 2,6-dichlorobenzenethiol Chemical compound SC1=C(Cl)C=CC=C1Cl JBISHCXLCGVPGW-UHFFFAOYSA-N 0.000 description 1
- QCLJODDRBGKIRW-UHFFFAOYSA-N 2,6-dimethylbenzenethiol Chemical compound CC1=CC=CC(C)=C1S QCLJODDRBGKIRW-UHFFFAOYSA-N 0.000 description 1
- OEKIVKRGLWFSSZ-UHFFFAOYSA-N 2-(2,6-dimethylphenyl)sulfanylpropanedioic acid Chemical compound CC1=CC=CC(C)=C1SC(C(O)=O)C(O)=O OEKIVKRGLWFSSZ-UHFFFAOYSA-N 0.000 description 1
- DDBMSHRIJMMBTN-UHFFFAOYSA-N 2-(2-butan-2-ylphenyl)sulfanylpropanedioic acid Chemical compound CCC(C)C1=CC=CC=C1SC(C(O)=O)C(O)=O DDBMSHRIJMMBTN-UHFFFAOYSA-N 0.000 description 1
- XHWQHQNKDPCFDS-UHFFFAOYSA-N 2-(2-chlorophenyl)ethoxy-(4-methylphenyl)-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound C1=CC(C)=CC=C1S(=O)(=S)OCCC1=CC=CC=C1Cl XHWQHQNKDPCFDS-UHFFFAOYSA-N 0.000 description 1
- XXSLLMSQVAPGAX-UHFFFAOYSA-N 2-(2-ethylphenyl)sulfanylpropanedioic acid Chemical compound CCC1=CC=CC=C1SC(C(O)=O)C(O)=O XXSLLMSQVAPGAX-UHFFFAOYSA-N 0.000 description 1
- AGOQHEGEVJJCND-UHFFFAOYSA-N 2-(3,5-dimethylphenyl)sulfanylpropanedioic acid Chemical compound CC1=CC(C)=CC(SC(C(O)=O)C(O)=O)=C1 AGOQHEGEVJJCND-UHFFFAOYSA-N 0.000 description 1
- 125000000301 2-(3-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- UYFLJSPKJAUJED-UHFFFAOYSA-N 2-(3-methoxyphenyl)ethoxy-(4-methylphenyl)-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound COC1=CC=CC(CCOS(=O)(=S)C=2C=CC(C)=CC=2)=C1 UYFLJSPKJAUJED-UHFFFAOYSA-N 0.000 description 1
- XIMVIITUEMUMLY-UHFFFAOYSA-N 2-(3-methylphenyl)sulfanylpropanedioic acid Chemical compound CC1=CC=CC(SC(C(O)=O)C(O)=O)=C1 XIMVIITUEMUMLY-UHFFFAOYSA-N 0.000 description 1
- PYLLZQULEIKEHP-UHFFFAOYSA-N 2-(3-phenylpropylsulfanyl)propanedioic acid Chemical compound OC(=O)C(C(O)=O)SCCCC1=CC=CC=C1 PYLLZQULEIKEHP-UHFFFAOYSA-N 0.000 description 1
- NAKUKHBXYDKGFD-UHFFFAOYSA-N 2-(4-methoxyphenyl)ethoxy-(4-methylphenyl)-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound C1=CC(OC)=CC=C1CCOS(=O)(=S)C1=CC=C(C)C=C1 NAKUKHBXYDKGFD-UHFFFAOYSA-N 0.000 description 1
- AKBOPJIXQYEIIJ-UHFFFAOYSA-N 2-(cyclohexylmethoxy)-1-phenylethanone Chemical compound C=1C=CC=CC=1C(=O)COCC1CCCCC1 AKBOPJIXQYEIIJ-UHFFFAOYSA-N 0.000 description 1
- YYCDWTIJQUTZJO-UHFFFAOYSA-N 2-(naphthalen-2-ylmethylsulfanyl)propanedioic acid Chemical compound C1=CC=CC2=CC(CSC(C(=O)O)C(O)=O)=CC=C21 YYCDWTIJQUTZJO-UHFFFAOYSA-N 0.000 description 1
- RFCQDOVPMUSZMN-UHFFFAOYSA-N 2-Naphthalenethiol Chemical compound C1=CC=CC2=CC(S)=CC=C21 RFCQDOVPMUSZMN-UHFFFAOYSA-N 0.000 description 1
- MXCYPPNQAULBAA-UHFFFAOYSA-N 2-[(4-hydroxy-2-oxo-6-phenylpyran-3-yl)sulfanylmethyl]benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CSC1=C(O)C=C(C=2C=CC=CC=2)OC1=O MXCYPPNQAULBAA-UHFFFAOYSA-N 0.000 description 1
- NLDZHCDTXRUYDN-UHFFFAOYSA-N 2-[4-(4-hydroxy-3-methyl-6-oxo-5-phenylsulfanylpyran-2-yl)phenoxy]acetic acid Chemical compound O=C1OC(C=2C=CC(OCC(O)=O)=CC=2)=C(C)C(O)=C1SC1=CC=CC=C1 NLDZHCDTXRUYDN-UHFFFAOYSA-N 0.000 description 1
- UFPJNNAHXLOGCF-UHFFFAOYSA-N 2-[4-(4-hydroxy-6-oxo-5-phenylsulfanylpyran-2-yl)phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1C(OC1=O)=CC(O)=C1SC1=CC=CC=C1 UFPJNNAHXLOGCF-UHFFFAOYSA-N 0.000 description 1
- ZWVMLEVADZPJBJ-UHFFFAOYSA-N 2-[4-[4-hydroxy-6-oxo-5-(2-phenylethylsulfanyl)pyran-2-yl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1C(OC1=O)=CC(O)=C1SCCC1=CC=CC=C1 ZWVMLEVADZPJBJ-UHFFFAOYSA-N 0.000 description 1
- MQLNSWYLMREANS-UHFFFAOYSA-N 2-[4-[4-hydroxy-6-oxo-5-(2-propan-2-ylphenyl)sulfanylpyran-2-yl]phenoxy]acetic acid Chemical compound CC(C)C1=CC=CC=C1SC1=C(O)C=C(C=2C=CC(OCC(O)=O)=CC=2)OC1=O MQLNSWYLMREANS-UHFFFAOYSA-N 0.000 description 1
- IQHSSYROJYPFDV-UHFFFAOYSA-N 2-bromo-1,3-dichloro-5-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC(Cl)=C(Br)C(Cl)=C1 IQHSSYROJYPFDV-UHFFFAOYSA-N 0.000 description 1
- ILJKKAIQFPEIBL-UHFFFAOYSA-N 2-cyclopropyl-2-hydroxyacetonitrile Chemical compound N#CC(O)C1CC1 ILJKKAIQFPEIBL-UHFFFAOYSA-N 0.000 description 1
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 1
- MGOLNIXAPIAKFM-UHFFFAOYSA-N 2-isocyanato-2-methylpropane Chemical compound CC(C)(C)N=C=O MGOLNIXAPIAKFM-UHFFFAOYSA-N 0.000 description 1
- WXKWJQNTAQTITA-UHFFFAOYSA-N 2-naphthalen-1-ylsulfanylpropanedioic acid Chemical compound C1=CC=C2C(SC(C(=O)O)C(O)=O)=CC=CC2=C1 WXKWJQNTAQTITA-UHFFFAOYSA-N 0.000 description 1
- MBPHQYIKEHJHKF-UHFFFAOYSA-N 2-naphthalen-2-ylsulfanylpropanedioic acid Chemical compound C1=CC=CC2=CC(SC(C(=O)O)C(O)=O)=CC=C21 MBPHQYIKEHJHKF-UHFFFAOYSA-N 0.000 description 1
- MSIGTXLXMVOOQD-UHFFFAOYSA-N 2-phenoxyethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCOC1=CC=CC=C1 MSIGTXLXMVOOQD-UHFFFAOYSA-N 0.000 description 1
- VMZCDNSFRSVYKQ-UHFFFAOYSA-N 2-phenylacetyl chloride Chemical compound ClC(=O)CC1=CC=CC=C1 VMZCDNSFRSVYKQ-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- KGBXHAVIEYXXRU-UHFFFAOYSA-N 2h-thiopyran 1-oxide Chemical compound O=S1CC=CC=C1 KGBXHAVIEYXXRU-UHFFFAOYSA-N 0.000 description 1
- LTNUSYNQZJZUSY-UHFFFAOYSA-N 3,3-dimethylbutanal Chemical compound CC(C)(C)CC=O LTNUSYNQZJZUSY-UHFFFAOYSA-N 0.000 description 1
- BJGMDTFHOFUMBB-UHFFFAOYSA-N 3,4,5,6,7,8-hexachlorochromen-2-one Chemical compound ClC1=C(Cl)C(=O)OC2=C(Cl)C(Cl)=C(Cl)C(Cl)=C21 BJGMDTFHOFUMBB-UHFFFAOYSA-N 0.000 description 1
- VUGQIIQFXCXZJU-UHFFFAOYSA-N 3,4,5-trimethoxyacetophenone Chemical compound COC1=CC(C(C)=O)=CC(OC)=C1OC VUGQIIQFXCXZJU-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- LXAMEVRKDQYJFB-UHFFFAOYSA-N 3-(1-benzylsulfanyl-2-cyclopropylethyl)-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(SCC=1C=CC=CC=1)CC1CC1 LXAMEVRKDQYJFB-UHFFFAOYSA-N 0.000 description 1
- JLWYFHWLYZPNLA-UHFFFAOYSA-N 3-(1-benzylsulfanyl-3-methylbutyl)-6-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-hydroxypyran-2-one Chemical compound OC=1C=C(C=2C=C3OCCOC3=CC=2)OC(=O)C=1C(CC(C)C)SCC1=CC=CC=C1 JLWYFHWLYZPNLA-UHFFFAOYSA-N 0.000 description 1
- PYRLSOHLBKBNQV-UHFFFAOYSA-N 3-(1-cyclohexylsulfanyl-2-cyclopentylethyl)-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(SC1CCCCC1)CC1CCCC1 PYRLSOHLBKBNQV-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- SFOYPKZAAFHJEO-UHFFFAOYSA-N 3-(2-butan-2-ylphenyl)sulfanyl-4-hydroxy-6-phenylpyran-2-one Chemical compound CCC(C)C1=CC=CC=C1SC1=C(O)C=C(C=2C=CC=CC=2)OC1=O SFOYPKZAAFHJEO-UHFFFAOYSA-N 0.000 description 1
- NWCSXQQMSZJSHW-UHFFFAOYSA-N 3-(2-chlorophenyl)sulfanyl-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1SC1=CC=CC=C1Cl NWCSXQQMSZJSHW-UHFFFAOYSA-N 0.000 description 1
- DWPQVSSEABBDLA-UHFFFAOYSA-N 3-(2-cyclohexyl-1-cyclohexylsulfanylethyl)-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(SC1CCCCC1)CC1CCCCC1 DWPQVSSEABBDLA-UHFFFAOYSA-N 0.000 description 1
- QODPJXZWRQSLAI-UHFFFAOYSA-N 3-(2-ethylphenyl)sulfanyl-4-hydroxy-6-phenylpyran-2-one Chemical compound CCC1=CC=CC=C1SC1=C(O)C=C(C=2C=CC=CC=2)OC1=O QODPJXZWRQSLAI-UHFFFAOYSA-N 0.000 description 1
- FCVFWRSUVVZAGF-UHFFFAOYSA-N 3-(3-chlorophenyl)sulfanyl-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1SC1=CC=CC(Cl)=C1 FCVFWRSUVVZAGF-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- CBRAFUXGIKIARS-UHFFFAOYSA-N 3-(benzylamino)-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1NCC1=CC=CC=C1 CBRAFUXGIKIARS-UHFFFAOYSA-N 0.000 description 1
- ZWHWOVSVMNEBFA-UHFFFAOYSA-N 3-(benzylamino)-4-hydroxy-6-phenylpyran-2-one hydrochloride Chemical compound Cl.Oc1cc(oc(=O)c1NCc1ccccc1)-c1ccccc1 ZWHWOVSVMNEBFA-UHFFFAOYSA-N 0.000 description 1
- UEGXZUNCECKBCX-UHFFFAOYSA-N 3-(cyclopropylmethylsulfanyl)-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1SCC1CC1 UEGXZUNCECKBCX-UHFFFAOYSA-N 0.000 description 1
- DQHPTDBYSBGPHB-UHFFFAOYSA-N 3-(dibenzylamino)-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 DQHPTDBYSBGPHB-UHFFFAOYSA-N 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- RNIDWJDZNNVFDY-UHFFFAOYSA-N 3-Acetylthiophene Chemical compound CC(=O)C=1C=CSC=1 RNIDWJDZNNVFDY-UHFFFAOYSA-N 0.000 description 1
- OEWSQGPYZFPQDM-UHFFFAOYSA-N 3-[(2-benzylsulfanylpyridin-3-yl)methyl]-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1CC1=CC=CN=C1SCC1=CC=CC=C1 OEWSQGPYZFPQDM-UHFFFAOYSA-N 0.000 description 1
- KQVURKJHDOQVKT-UHFFFAOYSA-N 3-[(2-cyclohexylsulfanylpyridin-4-yl)methyl]-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1CC(C=1)=CC=NC=1SC1CCCCC1 KQVURKJHDOQVKT-UHFFFAOYSA-N 0.000 description 1
- CFCWWXNJEBXTDC-UHFFFAOYSA-N 3-[1-(cyclohexylmethylsulfanyl)-3-methylbutyl]-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(CC(C)C)SCC1CCCCC1 CFCWWXNJEBXTDC-UHFFFAOYSA-N 0.000 description 1
- MKAFMQHMRZFSHF-UHFFFAOYSA-N 3-[2-(cyclopropylmethyl)phenyl]sulfanyl-4-hydroxy-6-(3-phenylphenyl)pyran-2-one Chemical compound OC=1C=C(C=2C=C(C=CC=2)C=2C=CC=CC=2)OC(=O)C=1SC1=CC=CC=C1CC1CC1 MKAFMQHMRZFSHF-UHFFFAOYSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 1
- DDSLCAGQQNCFSB-UHFFFAOYSA-N 3-[bis(naphthalen-2-ylmethyl)amino]-4-hydroxy-6-phenylpyran-2-one Chemical compound O1C(=O)C(N(CC=2C=C3C=CC=CC3=CC=2)CC=2C=C3C=CC=CC3=CC=2)=C(O)C=C1C1=CC=CC=C1 DDSLCAGQQNCFSB-UHFFFAOYSA-N 0.000 description 1
- HUPNANYHWKPZFQ-UHFFFAOYSA-N 3-[cyclohexyl(phenylsulfanyl)methyl]-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(C1CCCCC1)SC1=CC=CC=C1 HUPNANYHWKPZFQ-UHFFFAOYSA-N 0.000 description 1
- CRMPDEQNMUEPTB-UHFFFAOYSA-N 3-[cyclohexylsulfanyl(phenyl)methyl]-4-hydroxy-6-[3-methyl-4-(pyridin-3-ylmethoxy)phenyl]pyran-2-one Chemical compound CC1=CC(C=2OC(=O)C(C(SC3CCCCC3)C=3C=CC=CC=3)=C(O)C=2)=CC=C1OCC1=CC=CN=C1 CRMPDEQNMUEPTB-UHFFFAOYSA-N 0.000 description 1
- ZLYKUIUJEAYAOR-UHFFFAOYSA-N 3-[cyclopentyl(cyclopentylsulfanyl)methyl]-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(C1CCCC1)SC1CCCC1 ZLYKUIUJEAYAOR-UHFFFAOYSA-N 0.000 description 1
- FGVDTXYRRQTART-UHFFFAOYSA-N 3-[cyclopropyl(phenyl)methyl]-4-hydroxy-6-(2-phenylpropan-2-yl)pyran-2-one Chemical compound C=1C(O)=C(C(C2CC2)C=2C=CC=CC=2)C(=O)OC=1C(C)(C)C1=CC=CC=C1 FGVDTXYRRQTART-UHFFFAOYSA-N 0.000 description 1
- TXOPSTZDOLCEGT-UHFFFAOYSA-N 3-benzoyl-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(=O)C1=CC=CC=C1 TXOPSTZDOLCEGT-UHFFFAOYSA-N 0.000 description 1
- BQSOMHCKQDTQDY-UHFFFAOYSA-N 3-benzylsulfanyl-4-hydroxy-6-(2,3,4-trimethoxyphenyl)pyran-2-one Chemical compound COC1=C(OC)C(OC)=CC=C1C(OC1=O)=CC(O)=C1SCC1=CC=CC=C1 BQSOMHCKQDTQDY-UHFFFAOYSA-N 0.000 description 1
- VRGVOKIADZOTNU-UHFFFAOYSA-N 3-benzylsulfanyl-4-hydroxy-6-(2,4,6-trimethylphenyl)pyran-2-one Chemical compound CC1=CC(C)=CC(C)=C1C(OC1=O)=CC(O)=C1SCC1=CC=CC=C1 VRGVOKIADZOTNU-UHFFFAOYSA-N 0.000 description 1
- JRDMEBSNLWKNLM-UHFFFAOYSA-N 3-benzylsulfanyl-4-hydroxy-6-(2-phenylethyl)pyran-2-one Chemical compound O1C(=O)C(SCC=2C=CC=CC=2)=C(O)C=C1CCC1=CC=CC=C1 JRDMEBSNLWKNLM-UHFFFAOYSA-N 0.000 description 1
- FVEMWMDOZAQFGE-UHFFFAOYSA-N 3-benzylsulfanyl-4-hydroxy-6-(3-hydroxyphenyl)pyran-2-one Chemical compound OC1=CC=CC(C=2OC(=O)C(SCC=3C=CC=CC=3)=C(O)C=2)=C1 FVEMWMDOZAQFGE-UHFFFAOYSA-N 0.000 description 1
- NVZVGKLRFXDTRT-UHFFFAOYSA-N 3-benzylsulfanyl-4-hydroxy-6-(3-methoxyphenyl)pyran-2-one Chemical compound COC1=CC=CC(C=2OC(=O)C(SCC=3C=CC=CC=3)=C(O)C=2)=C1 NVZVGKLRFXDTRT-UHFFFAOYSA-N 0.000 description 1
- LXFQYMRGGBXRFR-UHFFFAOYSA-N 3-benzylsulfanyl-4-hydroxy-6-(3-methylphenyl)pyran-2-one Chemical compound CC1=CC=CC(C=2OC(=O)C(SCC=3C=CC=CC=3)=C(O)C=2)=C1 LXFQYMRGGBXRFR-UHFFFAOYSA-N 0.000 description 1
- AGGZKTQUDDBSTB-UHFFFAOYSA-N 3-benzylsulfanyl-4-hydroxy-6-(4-hydroxy-3,5-dimethylphenyl)pyran-2-one Chemical compound CC1=C(O)C(C)=CC(C=2OC(=O)C(SCC=3C=CC=CC=3)=C(O)C=2)=C1 AGGZKTQUDDBSTB-UHFFFAOYSA-N 0.000 description 1
- LBSDTLGHJQKDCG-UHFFFAOYSA-N 3-benzylsulfanyl-4-hydroxy-6-(4-methoxyphenyl)pyran-2-one Chemical compound C1=CC(OC)=CC=C1C(OC1=O)=CC(O)=C1SCC1=CC=CC=C1 LBSDTLGHJQKDCG-UHFFFAOYSA-N 0.000 description 1
- HRQKATLKWZKTOX-UHFFFAOYSA-N 3-benzylsulfanyl-4-hydroxy-6-(4-methylphenyl)pyran-2-one Chemical compound C1=CC(C)=CC=C1C(OC1=O)=CC(O)=C1SCC1=CC=CC=C1 HRQKATLKWZKTOX-UHFFFAOYSA-N 0.000 description 1
- VCJPOKHDQYUPRC-UHFFFAOYSA-N 3-benzylsulfanyl-4-hydroxy-6-[3-(trifluoromethoxy)phenyl]pyran-2-one Chemical compound OC=1C=C(C=2C=C(OC(F)(F)F)C=CC=2)OC(=O)C=1SCC1=CC=CC=C1 VCJPOKHDQYUPRC-UHFFFAOYSA-N 0.000 description 1
- YBLPDUZVKFBVDZ-UHFFFAOYSA-N 3-benzylsulfanyl-4-hydroxy-6-[3-(trifluoromethyl)phenyl]pyran-2-one Chemical compound OC=1C=C(C=2C=C(C=CC=2)C(F)(F)F)OC(=O)C=1SCC1=CC=CC=C1 YBLPDUZVKFBVDZ-UHFFFAOYSA-N 0.000 description 1
- GTVMUKXAZYYXGL-UHFFFAOYSA-N 3-benzylsulfanyl-4-hydroxy-6-pyridin-3-ylpyran-2-one Chemical compound OC=1C=C(C=2C=NC=CC=2)OC(=O)C=1SCC1=CC=CC=C1 GTVMUKXAZYYXGL-UHFFFAOYSA-N 0.000 description 1
- AUFAFRMSWOIUKV-UHFFFAOYSA-N 3-benzylsulfanyl-4-hydroxy-6-thiophen-3-ylpyran-2-one Chemical compound OC=1C=C(C2=CSC=C2)OC(=O)C=1SCC1=CC=CC=C1 AUFAFRMSWOIUKV-UHFFFAOYSA-N 0.000 description 1
- JFFNKJAWFVAUCN-UHFFFAOYSA-N 3-benzylsulfanyl-6-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-hydroxypyran-2-one Chemical compound OC=1C=C(C=2C=C3OCCOC3=CC=2)OC(=O)C=1SCC1=CC=CC=C1 JFFNKJAWFVAUCN-UHFFFAOYSA-N 0.000 description 1
- ODTDDEVANCJAME-UHFFFAOYSA-N 3-benzylsulfanyl-6-(3,4-dichlorophenyl)-4-hydroxypyran-2-one Chemical compound OC=1C=C(C=2C=C(Cl)C(Cl)=CC=2)OC(=O)C=1SCC1=CC=CC=C1 ODTDDEVANCJAME-UHFFFAOYSA-N 0.000 description 1
- WMUIOSDSZNSGFG-UHFFFAOYSA-N 3-benzylsulfanyl-6-(3-chloro-4-methoxyphenyl)-4-hydroxypyran-2-one Chemical compound C1=C(Cl)C(OC)=CC=C1C(OC1=O)=CC(O)=C1SCC1=CC=CC=C1 WMUIOSDSZNSGFG-UHFFFAOYSA-N 0.000 description 1
- IPGQVHLTXHXRKQ-UHFFFAOYSA-N 3-benzylsulfonyl-4-hydroxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1S(=O)(=O)CC1=CC=CC=C1 IPGQVHLTXHXRKQ-UHFFFAOYSA-N 0.000 description 1
- PIEZXKIADRCNNE-UHFFFAOYSA-N 3-chloro-n-methoxy-n-methylbenzamide Chemical compound CON(C)C(=O)C1=CC=CC(Cl)=C1 PIEZXKIADRCNNE-UHFFFAOYSA-N 0.000 description 1
- XZBXAYCCBFTQHH-UHFFFAOYSA-N 3-chloropropylbenzene Chemical compound ClCCCC1=CC=CC=C1 XZBXAYCCBFTQHH-UHFFFAOYSA-N 0.000 description 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- HVNRZWGUDFNHNM-UHFFFAOYSA-N 3-nitropyran-2-one Chemical compound [O-][N+](=O)C1=CC=COC1=O HVNRZWGUDFNHNM-UHFFFAOYSA-N 0.000 description 1
- JGEMCAYMTXOGRB-UHFFFAOYSA-N 3-oxo-2-(2-propan-2-ylphenyl)-3-sulfanylpropanoic acid Chemical compound CC(C)C1=CC=CC=C1C(C(O)=O)C(S)=O JGEMCAYMTXOGRB-UHFFFAOYSA-N 0.000 description 1
- ADTMITDBGCYTKC-UHFFFAOYSA-N 3-phenylprop-2-enyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCC=CC1=CC=CC=C1 ADTMITDBGCYTKC-UHFFFAOYSA-N 0.000 description 1
- VJPPLCNBDLZIFG-ZDUSSCGKSA-N 4-[(3S)-3-(but-2-ynoylamino)piperidin-1-yl]-5-fluoro-2,3-dimethyl-1H-indole-7-carboxamide Chemical compound C(C#CC)(=O)N[C@@H]1CN(CCC1)C1=C2C(=C(NC2=C(C=C1F)C(=O)N)C)C VJPPLCNBDLZIFG-ZDUSSCGKSA-N 0.000 description 1
- CMSRVCROZCDHEB-UHFFFAOYSA-N 4-[(4-hydroxy-2-oxo-6-phenylpyran-3-yl)sulfanylmethyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CSC1=C(O)C=C(C=2C=CC=CC=2)OC1=O CMSRVCROZCDHEB-UHFFFAOYSA-N 0.000 description 1
- YFCIFWOJYYFDQP-PTWZRHHISA-N 4-[3-amino-6-[(1S,3S,4S)-3-fluoro-4-hydroxycyclohexyl]pyrazin-2-yl]-N-[(1S)-1-(3-bromo-5-fluorophenyl)-2-(methylamino)ethyl]-2-fluorobenzamide Chemical compound CNC[C@@H](NC(=O)c1ccc(cc1F)-c1nc(cnc1N)[C@H]1CC[C@H](O)[C@@H](F)C1)c1cc(F)cc(Br)c1 YFCIFWOJYYFDQP-PTWZRHHISA-N 0.000 description 1
- LKLWYRQYDSCGAV-UHFFFAOYSA-N 4-[[2-[4-hydroxy-6-oxo-5-(2-phenylethylsulfanyl)pyran-2-yl]phenoxy]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1COC1=CC=CC=C1C(OC1=O)=CC(O)=C1SCCC1=CC=CC=C1 LKLWYRQYDSCGAV-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- KHEABNLTWKPDEL-UHFFFAOYSA-N 4-bromopyran-2-one Chemical compound BrC=1C=COC(=O)C=1 KHEABNLTWKPDEL-UHFFFAOYSA-N 0.000 description 1
- LHUOAIXJPPMULP-UHFFFAOYSA-N 4-chloro-n-methoxy-n-methylbenzamide Chemical compound CON(C)C(=O)C1=CC=C(Cl)C=C1 LHUOAIXJPPMULP-UHFFFAOYSA-N 0.000 description 1
- 229940073735 4-hydroxy acetophenone Drugs 0.000 description 1
- IAMNVCJECQWBLZ-UHFFFAOYSA-N 4-hydroxy-2-methylacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1C IAMNVCJECQWBLZ-UHFFFAOYSA-N 0.000 description 1
- CNGDTISDNGHIRB-UHFFFAOYSA-N 4-hydroxy-3-(2-methoxyphenyl)sulfanyl-6-phenylpyran-2-one Chemical compound COC1=CC=CC=C1SC1=C(O)C=C(C=2C=CC=CC=2)OC1=O CNGDTISDNGHIRB-UHFFFAOYSA-N 0.000 description 1
- QOMZDTQJJCIQCR-UHFFFAOYSA-N 4-hydroxy-3-(2-methylphenyl)sulfanyl-6-phenylpyran-2-one Chemical compound CC1=CC=CC=C1SC1=C(O)C=C(C=2C=CC=CC=2)OC1=O QOMZDTQJJCIQCR-UHFFFAOYSA-N 0.000 description 1
- OMHGORRGLOGKCE-UHFFFAOYSA-N 4-hydroxy-3-(2-phenoxyethylsulfanyl)-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1SCCOC1=CC=CC=C1 OMHGORRGLOGKCE-UHFFFAOYSA-N 0.000 description 1
- IUVAWIVQWBFTKP-UHFFFAOYSA-N 4-hydroxy-3-(2-phenylethylsulfanyl)-6-(3-phenylphenyl)pyran-2-one Chemical compound OC=1C=C(C=2C=C(C=CC=2)C=2C=CC=CC=2)OC(=O)C=1SCCC1=CC=CC=C1 IUVAWIVQWBFTKP-UHFFFAOYSA-N 0.000 description 1
- BWGOFFDTAAIACE-UHFFFAOYSA-N 4-hydroxy-3-(2-phenylethylsulfanyl)-6-(4-phenylmethoxyphenyl)pyran-2-one Chemical compound OC=1C=C(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)OC(=O)C=1SCCC1=CC=CC=C1 BWGOFFDTAAIACE-UHFFFAOYSA-N 0.000 description 1
- QZGXCARVSIMYDJ-UHFFFAOYSA-N 4-hydroxy-3-(2-phenylethylsulfanyl)-6-(4-phenylsulfanylphenyl)pyran-2-one Chemical compound OC=1C=C(C=2C=CC(SC=3C=CC=CC=3)=CC=2)OC(=O)C=1SCCC1=CC=CC=C1 QZGXCARVSIMYDJ-UHFFFAOYSA-N 0.000 description 1
- ILXNPKRIBNXRDH-UHFFFAOYSA-N 4-hydroxy-3-(2-phenylethylsulfanyl)-6-[4-(3-phenylpropoxy)phenyl]pyran-2-one Chemical compound OC=1C=C(C=2C=CC(OCCCC=3C=CC=CC=3)=CC=2)OC(=O)C=1SCCC1=CC=CC=C1 ILXNPKRIBNXRDH-UHFFFAOYSA-N 0.000 description 1
- QSDASCFBUIJCGK-UHFFFAOYSA-N 4-hydroxy-3-(2-phenylethylsulfanyl)-6-[4-(pyridin-4-ylmethoxy)phenyl]pyran-2-one Chemical compound OC=1C=C(C=2C=CC(OCC=3C=CN=CC=3)=CC=2)OC(=O)C=1SCCC1=CC=CC=C1 QSDASCFBUIJCGK-UHFFFAOYSA-N 0.000 description 1
- QYCAGARHBLPUDC-UHFFFAOYSA-N 4-hydroxy-3-(2-phenylethylsulfanyl)-6-pyridin-4-ylpyran-2-one Chemical compound OC=1C=C(C=2C=CN=CC=2)OC(=O)C=1SCCC1=CC=CC=C1 QYCAGARHBLPUDC-UHFFFAOYSA-N 0.000 description 1
- FOHVXQOBTBULQP-UHFFFAOYSA-N 4-hydroxy-3-(3-methoxyphenyl)sulfanyl-6-phenylpyran-2-one Chemical compound COC1=CC=CC(SC=2C(OC(=CC=2O)C=2C=CC=CC=2)=O)=C1 FOHVXQOBTBULQP-UHFFFAOYSA-N 0.000 description 1
- TYUHNYJTJXZPCY-UHFFFAOYSA-N 4-hydroxy-3-(3-methylphenyl)sulfanyl-6-phenylpyran-2-one Chemical compound CC1=CC=CC(SC=2C(OC(=CC=2O)C=2C=CC=CC=2)=O)=C1 TYUHNYJTJXZPCY-UHFFFAOYSA-N 0.000 description 1
- FETCWWKTHLNBDV-UHFFFAOYSA-N 4-hydroxy-3-(4-hydroxy-2-oxo-6-phenylpyran-3-yl)sulfanyl-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1SC(C(O1)=O)=C(O)C=C1C1=CC=CC=C1 FETCWWKTHLNBDV-UHFFFAOYSA-N 0.000 description 1
- MGCMBIMEXGWKLH-UHFFFAOYSA-N 4-hydroxy-3-[(2-methoxyphenyl)methylsulfanyl]-6-phenylpyran-2-one Chemical compound COC1=CC=CC=C1CSC1=C(O)C=C(C=2C=CC=CC=2)OC1=O MGCMBIMEXGWKLH-UHFFFAOYSA-N 0.000 description 1
- SOOSEFXARDVQQN-UHFFFAOYSA-N 4-hydroxy-3-[(3-methoxyphenyl)methylsulfanyl]-6-phenylpyran-2-one Chemical compound COC1=CC=CC(CSC=2C(OC(=CC=2O)C=2C=CC=CC=2)=O)=C1 SOOSEFXARDVQQN-UHFFFAOYSA-N 0.000 description 1
- WMSBSVNHGFBMSQ-UHFFFAOYSA-N 4-hydroxy-3-[(3-methylphenyl)methylsulfanyl]-6-phenylpyran-2-one Chemical compound CC1=CC=CC(CSC=2C(OC(=CC=2O)C=2C=CC=CC=2)=O)=C1 WMSBSVNHGFBMSQ-UHFFFAOYSA-N 0.000 description 1
- ARXBIFAUPRSMOI-UHFFFAOYSA-N 4-hydroxy-3-[(3-phenoxyphenyl)methylsulfanyl]-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1SCC(C=1)=CC=CC=1OC1=CC=CC=C1 ARXBIFAUPRSMOI-UHFFFAOYSA-N 0.000 description 1
- PYHURBIUXYLCJJ-UHFFFAOYSA-N 4-hydroxy-3-[(4-hydroxy-2-oxo-6-phenylpyran-3-yl)disulfanyl]-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1SSC(C(O1)=O)=C(O)C=C1C1=CC=CC=C1 PYHURBIUXYLCJJ-UHFFFAOYSA-N 0.000 description 1
- PTTRVYOYJOLXDP-UHFFFAOYSA-N 4-hydroxy-3-[(4-methylphenyl)methylsulfanyl]-6-phenylpyran-2-one Chemical compound C1=CC(C)=CC=C1CSC1=C(O)C=C(C=2C=CC=CC=2)OC1=O PTTRVYOYJOLXDP-UHFFFAOYSA-N 0.000 description 1
- UHDQWUARHYVHJU-UHFFFAOYSA-N 4-hydroxy-3-[1-(2-methoxyphenyl)sulfanyl-3-methylbutyl]-6-phenylpyran-2-one Chemical compound COC1=CC=CC=C1SC(CC(C)C)C1=C(O)C=C(C=2C=CC=CC=2)OC1=O UHDQWUARHYVHJU-UHFFFAOYSA-N 0.000 description 1
- PZVUTIHYGWBYCK-UHFFFAOYSA-N 4-hydroxy-3-[2-(2-methoxyphenyl)ethylsulfanyl]-6-phenylpyran-2-one Chemical compound COC1=CC=CC=C1CCSC1=C(O)C=C(C=2C=CC=CC=2)OC1=O PZVUTIHYGWBYCK-UHFFFAOYSA-N 0.000 description 1
- CMODVCFVSYPNFP-UHFFFAOYSA-N 4-hydroxy-3-[2-(2-methylpropyl)phenyl]sulfanyl-6-phenylpyran-2-one Chemical compound CC(C)CC1=CC=CC=C1SC1=C(O)C=C(C=2C=CC=CC=2)OC1=O CMODVCFVSYPNFP-UHFFFAOYSA-N 0.000 description 1
- LVYJRUOGOMYIRE-UHFFFAOYSA-N 4-hydroxy-3-[2-(4-methoxyphenyl)ethylsulfanyl]-6-phenylpyran-2-one Chemical compound C1=CC(OC)=CC=C1CCSC1=C(O)C=C(C=2C=CC=CC=2)OC1=O LVYJRUOGOMYIRE-UHFFFAOYSA-N 0.000 description 1
- ILJCGLZYCHVSFD-UHFFFAOYSA-N 4-hydroxy-3-naphthalen-1-ylsulfanyl-6-phenylpyran-2-one Chemical compound O1C(=O)C(SC=2C3=CC=CC=C3C=CC=2)=C(O)C=C1C1=CC=CC=C1 ILJCGLZYCHVSFD-UHFFFAOYSA-N 0.000 description 1
- VODLQPORJLJQHS-UHFFFAOYSA-N 4-hydroxy-3-naphthalen-2-ylsulfanyl-6-(3-phenylphenyl)pyran-2-one Chemical compound O1C(=O)C(SC=2C=C3C=CC=CC3=CC=2)=C(O)C=C1C(C=1)=CC=CC=1C1=CC=CC=C1 VODLQPORJLJQHS-UHFFFAOYSA-N 0.000 description 1
- CUXBYEWFJNMRCE-UHFFFAOYSA-N 4-hydroxy-3-phenoxy-6-phenylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1OC1=CC=CC=C1 CUXBYEWFJNMRCE-UHFFFAOYSA-N 0.000 description 1
- KCUJQVDNFIZMOJ-UHFFFAOYSA-N 4-hydroxy-6-(2-hydroxy-3-methyl-4-phenylmethoxyphenyl)-3-(2-phenylethylsulfanyl)pyran-2-one Chemical compound CC1=C(O)C(C=2OC(=O)C(SCCC=3C=CC=CC=3)=C(O)C=2)=CC=C1OCC1=CC=CC=C1 KCUJQVDNFIZMOJ-UHFFFAOYSA-N 0.000 description 1
- QXQYYOWFJAICOZ-UHFFFAOYSA-N 4-hydroxy-6-(3-hydroxyphenyl)-3-(2-propan-2-ylphenyl)sulfanylpyran-2-one Chemical compound CC(C)C1=CC=CC=C1SC1=C(O)C=C(C=2C=C(O)C=CC=2)OC1=O QXQYYOWFJAICOZ-UHFFFAOYSA-N 0.000 description 1
- KMUSZVVUGZOWGC-UHFFFAOYSA-N 4-hydroxy-6-(3-methyl-4-phenylmethoxyphenyl)-3-(2-phenylethylsulfanyl)pyran-2-one Chemical compound CC1=CC(C=2OC(=O)C(SCCC=3C=CC=CC=3)=C(O)C=2)=CC=C1OCC1=CC=CC=C1 KMUSZVVUGZOWGC-UHFFFAOYSA-N 0.000 description 1
- BKNRFORSMDDBON-UHFFFAOYSA-N 4-hydroxy-6-(3-phenoxyphenyl)-3-(2-phenylethylsulfanyl)pyran-2-one Chemical compound OC=1C=C(C=2C=C(OC=3C=CC=CC=3)C=CC=2)OC(=O)C=1SCCC1=CC=CC=C1 BKNRFORSMDDBON-UHFFFAOYSA-N 0.000 description 1
- JYJAUMHYINNSOC-UHFFFAOYSA-N 4-hydroxy-6-(4-hydroxy-2-methylphenyl)-3-(2-phenylethylsulfanyl)pyran-2-one Chemical compound CC1=CC(O)=CC=C1C(OC1=O)=CC(O)=C1SCCC1=CC=CC=C1 JYJAUMHYINNSOC-UHFFFAOYSA-N 0.000 description 1
- PSMFZJGARFLDCA-UHFFFAOYSA-N 4-hydroxy-6-(4-hydroxyphenyl)-3-(2-propan-2-ylphenyl)sulfanylpyran-2-one Chemical compound CC(C)C1=CC=CC=C1SC1=C(O)C=C(C=2C=CC(O)=CC=2)OC1=O PSMFZJGARFLDCA-UHFFFAOYSA-N 0.000 description 1
- UQPJNOYPZHQCTL-UHFFFAOYSA-N 4-hydroxy-6-(4-methoxyphenyl)-3-(2-propan-2-ylphenyl)sulfanylpyran-2-one Chemical compound C1=CC(OC)=CC=C1C(OC1=O)=CC(O)=C1SC1=CC=CC=C1C(C)C UQPJNOYPZHQCTL-UHFFFAOYSA-N 0.000 description 1
- UNJBAMMFCYVYFS-UHFFFAOYSA-N 4-hydroxy-6-(4-phenoxyphenyl)-3-(2-phenylethylsulfanyl)pyran-2-one Chemical compound OC=1C=C(C=2C=CC(OC=3C=CC=CC=3)=CC=2)OC(=O)C=1SCCC1=CC=CC=C1 UNJBAMMFCYVYFS-UHFFFAOYSA-N 0.000 description 1
- BHDDRHSBFADMOP-UHFFFAOYSA-N 4-hydroxy-6-[3-(2-phenylethoxy)phenyl]-3-(2-phenylethylsulfanyl)pyran-2-one Chemical compound OC=1C=C(C=2C=C(OCCC=3C=CC=CC=3)C=CC=2)OC(=O)C=1SCCC1=CC=CC=C1 BHDDRHSBFADMOP-UHFFFAOYSA-N 0.000 description 1
- XVUQUYDAICOATD-UHFFFAOYSA-N 4-hydroxy-6-[4-(2-hydroxyethoxy)phenyl]-3-(2-phenylethylsulfanyl)pyran-2-one Chemical compound C1=CC(OCCO)=CC=C1C(OC1=O)=CC(O)=C1SCCC1=CC=CC=C1 XVUQUYDAICOATD-UHFFFAOYSA-N 0.000 description 1
- AASCUWWQEASKFU-UHFFFAOYSA-N 4-hydroxy-6-[4-(2-phenylethoxy)phenyl]-3-(2-phenylethylsulfanyl)pyran-2-one Chemical compound OC=1C=C(C=2C=CC(OCCC=3C=CC=CC=3)=CC=2)OC(=O)C=1SCCC1=CC=CC=C1 AASCUWWQEASKFU-UHFFFAOYSA-N 0.000 description 1
- DRNLVLSDCRCOIU-UHFFFAOYSA-N 4-hydroxy-6-[4-(naphthalen-2-ylmethoxy)phenyl]-3-(2-phenylethylsulfanyl)pyran-2-one Chemical compound OC=1C=C(C=2C=CC(OCC=3C=C4C=CC=CC4=CC=3)=CC=2)OC(=O)C=1SCCC1=CC=CC=C1 DRNLVLSDCRCOIU-UHFFFAOYSA-N 0.000 description 1
- DZVVSDVOMGWWLO-UHFFFAOYSA-N 4-hydroxy-6-phenyl-3-(2-phenyl-1-phenylsulfanylethyl)pyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(SC=1C=CC=CC=1)CC1=CC=CC=C1 DZVVSDVOMGWWLO-UHFFFAOYSA-N 0.000 description 1
- FVVZOINQRVFHHQ-UHFFFAOYSA-N 4-hydroxy-6-phenyl-3-(2-phenylethyl)pyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1CCC1=CC=CC=C1 FVVZOINQRVFHHQ-UHFFFAOYSA-N 0.000 description 1
- NRCCWHIONCHZCL-UHFFFAOYSA-N 4-hydroxy-6-phenyl-3-(2-phenylethylsulfanyl)pyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1SCCC1=CC=CC=C1 NRCCWHIONCHZCL-UHFFFAOYSA-N 0.000 description 1
- GPSNJPSAMISEND-UHFFFAOYSA-N 4-hydroxy-6-phenyl-3-(2-propan-2-ylphenoxy)pyran-2-one Chemical compound CC(C)C1=CC=CC=C1OC1=C(O)C=C(C=2C=CC=CC=2)OC1=O GPSNJPSAMISEND-UHFFFAOYSA-N 0.000 description 1
- KLTMLVONBRVJAF-UHFFFAOYSA-N 4-hydroxy-6-phenyl-3-(3-phenylpropyl)pyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1CCCC1=CC=CC=C1 KLTMLVONBRVJAF-UHFFFAOYSA-N 0.000 description 1
- NLLRFWVAGAQZLA-UHFFFAOYSA-N 4-hydroxy-6-phenyl-3-(3-phenylpropylsulfanyl)pyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1SCCCC1=CC=CC=C1 NLLRFWVAGAQZLA-UHFFFAOYSA-N 0.000 description 1
- RCPMZSUZCGCWJB-UHFFFAOYSA-N 4-hydroxy-6-phenyl-3-(4-phenylbutylsulfanyl)pyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1SCCCCC1=CC=CC=C1 RCPMZSUZCGCWJB-UHFFFAOYSA-N 0.000 description 1
- OJBKXSNCDMDSJX-UHFFFAOYSA-N 4-hydroxy-6-phenyl-3-(phenylsulfanylmethyl)pyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1CSC1=CC=CC=C1 OJBKXSNCDMDSJX-UHFFFAOYSA-N 0.000 description 1
- SMAMDVPQCXQMOO-UHFFFAOYSA-N 4-hydroxy-6-phenyl-3-[(3-phenylmethoxyphenyl)methylsulfanyl]pyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1SCC(C=1)=CC=CC=1OCC1=CC=CC=C1 SMAMDVPQCXQMOO-UHFFFAOYSA-N 0.000 description 1
- BEXHBNJENAYVPW-UHFFFAOYSA-N 4-hydroxy-6-phenyl-3-[(4-phenylmethoxyphenyl)methylsulfanyl]pyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1SCC(C=C1)=CC=C1OCC1=CC=CC=C1 BEXHBNJENAYVPW-UHFFFAOYSA-N 0.000 description 1
- HBEXQJCORANPPR-UHFFFAOYSA-N 4-hydroxy-6-phenyl-3-[3-(trifluoromethyl)phenyl]sulfanylpyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1SC1=CC=CC(C(F)(F)F)=C1 HBEXQJCORANPPR-UHFFFAOYSA-N 0.000 description 1
- QRIZAXHQKYKILR-UHFFFAOYSA-N 4-hydroxy-6-phenyl-3-[[3-(2-phenylethoxy)phenyl]methylsulfanyl]pyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1SCC(C=1)=CC=CC=1OCCC1=CC=CC=C1 QRIZAXHQKYKILR-UHFFFAOYSA-N 0.000 description 1
- LVOUHVQQFFTPTD-UHFFFAOYSA-N 4-hydroxy-6-phenyl-3-[phenyl(phenylsulfanyl)methyl]pyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(C=1C=CC=CC=1)SC1=CC=CC=C1 LVOUHVQQFFTPTD-UHFFFAOYSA-N 0.000 description 1
- CPJPEEYFZAKNAH-UHFFFAOYSA-N 4-hydroxy-6-phenyl-3-sulfanylpyran-2-one Chemical compound O1C(=O)C(S)=C(O)C=C1C1=CC=CC=C1 CPJPEEYFZAKNAH-UHFFFAOYSA-N 0.000 description 1
- JGEGJYXHCFUMJF-UHFFFAOYSA-N 4-methylpentanal Chemical compound CC(C)CCC=O JGEGJYXHCFUMJF-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- AUWKJEFRRUACBH-UHFFFAOYSA-N 6-(1,3-benzodioxol-5-yl)-3-benzylsulfanyl-4-hydroxypyran-2-one Chemical compound OC=1C=C(C=2C=C3OCOC3=CC=2)OC(=O)C=1SCC1=CC=CC=C1 AUWKJEFRRUACBH-UHFFFAOYSA-N 0.000 description 1
- XVQFETLYNZIHQJ-UHFFFAOYSA-N 6-(1-benzylcyclopentyl)-3-(1-cyclopentylsulfanyl-3-methylbutyl)-4-hydroxypyran-2-one Chemical compound OC=1C=C(C2(CC=3C=CC=CC=3)CCCC2)OC(=O)C=1C(CC(C)C)SC1CCCC1 XVQFETLYNZIHQJ-UHFFFAOYSA-N 0.000 description 1
- HIUUNUFZJKAPPA-UHFFFAOYSA-N 6-(2,3-dihydro-1,4-benzodioxin-6-yl)-4-hydroxy-3-(2-propan-2-ylphenyl)sulfanylpyran-2-one Chemical compound CC(C)C1=CC=CC=C1SC1=C(O)C=C(C=2C=C3OCCOC3=CC=2)OC1=O HIUUNUFZJKAPPA-UHFFFAOYSA-N 0.000 description 1
- WYINEUBBIWELLW-UHFFFAOYSA-N 6-(3,5-dichlorophenyl)-4-hydroxy-3-(2-propan-2-ylphenyl)sulfanylpyran-2-one Chemical compound CC(C)C1=CC=CC=C1SC1=C(O)C=C(C=2C=C(Cl)C=C(Cl)C=2)OC1=O WYINEUBBIWELLW-UHFFFAOYSA-N 0.000 description 1
- PYVOSMCENJZPJP-UHFFFAOYSA-N 6-(3,5-dimethylphenyl)-4-hydroxy-3-(2-phenylethylsulfanyl)pyran-2-one Chemical compound CC1=CC(C)=CC(C=2OC(=O)C(SCCC=3C=CC=CC=3)=C(O)C=2)=C1 PYVOSMCENJZPJP-UHFFFAOYSA-N 0.000 description 1
- PQLMBHNVFJYRDU-UHFFFAOYSA-N 6-(3,5-dimethylphenyl)-4-hydroxy-3-(2-propan-2-ylphenyl)sulfanylpyran-2-one Chemical compound CC(C)C1=CC=CC=C1SC1=C(O)C=C(C=2C=C(C)C=C(C)C=2)OC1=O PQLMBHNVFJYRDU-UHFFFAOYSA-N 0.000 description 1
- YQBHRDATHPUCGN-UHFFFAOYSA-N 6-(3,5-dimethylphenyl)-4-hydroxy-3-phenylsulfanylpyran-2-one Chemical compound CC1=CC(C)=CC(C=2OC(=O)C(SC=3C=CC=CC=3)=C(O)C=2)=C1 YQBHRDATHPUCGN-UHFFFAOYSA-N 0.000 description 1
- VPVHIHBPSICTFT-UHFFFAOYSA-N 6-(3-chlorophenyl)-4-hydroxy-3-(2-phenylethylsulfanyl)pyran-2-one Chemical compound OC=1C=C(C=2C=C(Cl)C=CC=2)OC(=O)C=1SCCC1=CC=CC=C1 VPVHIHBPSICTFT-UHFFFAOYSA-N 0.000 description 1
- SKZIETYYFMFBNM-UHFFFAOYSA-N 6-(3-chlorophenyl)-4-hydroxy-3-(2-propan-2-ylphenyl)sulfanylpyran-2-one Chemical compound CC(C)C1=CC=CC=C1SC1=C(O)C=C(C=2C=C(Cl)C=CC=2)OC1=O SKZIETYYFMFBNM-UHFFFAOYSA-N 0.000 description 1
- AWRMBBAPWAFROS-UHFFFAOYSA-N 6-(3-chlorophenyl)-4-hydroxy-3-(4-phenylbutylsulfanyl)pyran-2-one Chemical compound OC=1C=C(C=2C=C(Cl)C=CC=2)OC(=O)C=1SCCCCC1=CC=CC=C1 AWRMBBAPWAFROS-UHFFFAOYSA-N 0.000 description 1
- FQWLRVSXZMXFGM-UHFFFAOYSA-N 6-[4-(benzenesulfonyl)phenyl]-4-hydroxy-3-(2-phenylethylsulfanyl)pyran-2-one Chemical compound OC=1C=C(C=2C=CC(=CC=2)S(=O)(=O)C=2C=CC=CC=2)OC(=O)C=1SCCC1=CC=CC=C1 FQWLRVSXZMXFGM-UHFFFAOYSA-N 0.000 description 1
- NROFPJRBKHILJM-UHFFFAOYSA-N 6-methylpyran-2-one Chemical compound CC1=CC=CC(=O)O1 NROFPJRBKHILJM-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
- 108091005502 Aspartic proteases Proteins 0.000 description 1
- 102000035101 Aspartic proteases Human genes 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000714197 Avian myeloblastosis-associated virus Species 0.000 description 1
- BWHOZHOGCMHOBV-UHFFFAOYSA-N Benzalacetone Natural products CC(=O)C=CC1=CC=CC=C1 BWHOZHOGCMHOBV-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- HSOOAWATECWQGM-UHFFFAOYSA-N C1(=CC=C(C=C1)S(=O)(OCC1=CC=C(C=C1)C(=O)OC)=S)C Chemical compound C1(=CC=C(C=C1)S(=O)(OCC1=CC=C(C=C1)C(=O)OC)=S)C HSOOAWATECWQGM-UHFFFAOYSA-N 0.000 description 1
- SZDSNUWLVKPQRA-UHFFFAOYSA-N CCOC(=O)C(C(=O)OCC)OC1=CC=CC=C1C(C)C Chemical compound CCOC(=O)C(C(=O)OCC)OC1=CC=CC=C1C(C)C SZDSNUWLVKPQRA-UHFFFAOYSA-N 0.000 description 1
- 101100232080 Caenorhabditis elegans hsr-9 gene Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- GKKZMYDNDDMXSE-UHFFFAOYSA-N Ethyl 3-oxo-3-phenylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CC=C1 GKKZMYDNDDMXSE-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- GISRWBROCYNDME-PELMWDNLSA-N F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C Chemical compound F[C@H]1[C@H]([C@H](NC1=O)COC1=NC=CC2=CC(=C(C=C12)OC)C(=O)N)C GISRWBROCYNDME-PELMWDNLSA-N 0.000 description 1
- 241000713800 Feline immunodeficiency virus Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 208000037357 HIV infectious disease Diseases 0.000 description 1
- 229940122440 HIV protease inhibitor Drugs 0.000 description 1
- 241000713340 Human immunodeficiency virus 2 Species 0.000 description 1
- 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 1
- 206010061598 Immunodeficiency Diseases 0.000 description 1
- 208000029462 Immunodeficiency disease Diseases 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
- 239000012448 Lithium borohydride Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- 238000006174 Newman-Kwart rearrangement reaction Methods 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- XGJQGEQHHDEVEW-UHFFFAOYSA-N P(=O)(=O)S(=O)(=O)O Chemical compound P(=O)(=O)S(=O)(=O)O XGJQGEQHHDEVEW-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 241000276498 Pollachius virens Species 0.000 description 1
- 101150085390 RPM1 gene Proteins 0.000 description 1
- 241000714474 Rous sarcoma virus Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- AISPQTWQZFJFQK-UHFFFAOYSA-N [2-oxo-6-phenyl-3-(2-propan-2-ylphenyl)sulfanylpyran-4-yl] acetate Chemical compound CC(C)C1=CC=CC=C1SC1=C(OC(C)=O)C=C(C=2C=CC=CC=2)OC1=O AISPQTWQZFJFQK-UHFFFAOYSA-N 0.000 description 1
- FACKKAYZBORFDV-UHFFFAOYSA-N [4-(5-benzylsulfanyl-4-hydroxy-6-oxopyran-2-yl)phenyl] benzoate Chemical compound OC=1C=C(C=2C=CC(OC(=O)C=3C=CC=CC=3)=CC=2)OC(=O)C=1SCC1=CC=CC=C1 FACKKAYZBORFDV-UHFFFAOYSA-N 0.000 description 1
- YVHWNUUAGGSWPS-UHFFFAOYSA-N [4-[4-hydroxy-6-oxo-5-(2-phenylethylsulfanyl)pyran-2-yl]phenyl] benzoate Chemical compound OC=1C=C(C=2C=CC(OC(=O)C=3C=CC=CC=3)=CC=2)OC(=O)C=1SCCC1=CC=CC=C1 YVHWNUUAGGSWPS-UHFFFAOYSA-N 0.000 description 1
- QQIRAVWVGBTHMJ-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;lithium Chemical compound [Li].C[Si](C)(C)N[Si](C)(C)C QQIRAVWVGBTHMJ-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-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
- 239000003929 acidic solution Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005236 alkanoylamino group Chemical group 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000000746 allylic group Chemical group 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000002832 anti-viral assay Methods 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 235000021311 artificial sweeteners Nutrition 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- YCOXTKKNXUZSKD-UHFFFAOYSA-N as-o-xylenol Natural products CC1=CC=C(O)C=C1C YCOXTKKNXUZSKD-UHFFFAOYSA-N 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- OSJRGDBEYARHLX-UHFFFAOYSA-N azido(trimethyl)stannane Chemical compound [N-]=[N+]=[N-].C[Sn+](C)C OSJRGDBEYARHLX-UHFFFAOYSA-N 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N benzo-alpha-pyrone Natural products C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- WXBLLCUINBKULX-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1 WXBLLCUINBKULX-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N benzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- NHYXMAKLBXBVEO-UHFFFAOYSA-N bromomethyl acetate Chemical compound CC(=O)OCBr NHYXMAKLBXBVEO-UHFFFAOYSA-N 0.000 description 1
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 201000001883 cholelithiasis Diseases 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000011443 conventional therapy Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000001671 coumarin Nutrition 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
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ARDSTDRKZYGHHV-UHFFFAOYSA-N cyclohexylmethoxy-(4-methylphenyl)-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound C1=CC(C)=CC=C1S(=O)(=S)OCC1CCCCC1 ARDSTDRKZYGHHV-UHFFFAOYSA-N 0.000 description 1
- VELDYOPRLMJFIK-UHFFFAOYSA-N cyclopentanecarbaldehyde Chemical compound O=CC1CCCC1 VELDYOPRLMJFIK-UHFFFAOYSA-N 0.000 description 1
- JFISEKJHWMFZBM-UHFFFAOYSA-N cyclopropylmethoxy-(4-methylphenyl)-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound C1=CC(C)=CC=C1S(=O)(=S)OCC1CC1 JFISEKJHWMFZBM-UHFFFAOYSA-N 0.000 description 1
- 230000000120 cytopathologic effect Effects 0.000 description 1
- 238000002784 cytotoxicity assay Methods 0.000 description 1
- 231100000263 cytotoxicity test Toxicity 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- SPXJKKPHXJCQBM-UHFFFAOYSA-N diethyl 2-(2-chlorophenyl)sulfanylpropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)SC1=CC=CC=C1Cl SPXJKKPHXJCQBM-UHFFFAOYSA-N 0.000 description 1
- GWUCFLFVEOWPJJ-UHFFFAOYSA-N diethyl 2-(2-methoxyphenyl)sulfanylpropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)SC1=CC=CC=C1OC GWUCFLFVEOWPJJ-UHFFFAOYSA-N 0.000 description 1
- HPTQAPHZYFNDKF-UHFFFAOYSA-N diethyl 2-(2-methylphenyl)sulfanylpropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)SC1=CC=CC=C1C HPTQAPHZYFNDKF-UHFFFAOYSA-N 0.000 description 1
- IZADBPZQVVKYJF-UHFFFAOYSA-N diethyl 2-(3-chlorophenyl)sulfanylpropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)SC1=CC=CC(Cl)=C1 IZADBPZQVVKYJF-UHFFFAOYSA-N 0.000 description 1
- ASEFVGWYBUAKDJ-UHFFFAOYSA-N diethyl 2-(3-phenylpropylsulfanyl)propanedioate Chemical compound CCOC(=O)C(C(=O)OCC)SCCCC1=CC=CC=C1 ASEFVGWYBUAKDJ-UHFFFAOYSA-N 0.000 description 1
- QJGKBJMARXARFE-UHFFFAOYSA-N diethyl 2-naphthalen-2-ylsulfanylpropanedioate Chemical compound C1=CC=CC2=CC(SC(C(=O)OCC)C(=O)OCC)=CC=C21 QJGKBJMARXARFE-UHFFFAOYSA-N 0.000 description 1
- CTRLRNRJBJRETO-UHFFFAOYSA-N diethyl 2-phenylsulfanylpropanedioate Chemical compound CCOC(=O)C(C(=O)OCC)SC1=CC=CC=C1 CTRLRNRJBJRETO-UHFFFAOYSA-N 0.000 description 1
- SGDINNZGYDHHKM-UHFFFAOYSA-N dilithium;trimethylsilylazanide Chemical compound [Li+].[Li+].C[Si](C)(C)[NH-].C[Si](C)(C)[NH-] SGDINNZGYDHHKM-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- ZEEZRIFIGWXBLX-UHFFFAOYSA-N ethyl 2-(3-acetylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=CC(C(C)=O)=C1 ZEEZRIFIGWXBLX-UHFFFAOYSA-N 0.000 description 1
- JLAOWXFXSSLUOZ-UHFFFAOYSA-N ethyl 2-(4-acetyl-2-methylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(C(C)=O)C=C1C JLAOWXFXSSLUOZ-UHFFFAOYSA-N 0.000 description 1
- RVNWZMJGLXVZEJ-UHFFFAOYSA-N ethyl 2-(4-acetylphenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(C(C)=O)C=C1 RVNWZMJGLXVZEJ-UHFFFAOYSA-N 0.000 description 1
- ACTFWSGUDLQVRL-UHFFFAOYSA-N ethyl 2-[3-[4-hydroxy-6-oxo-5-(2-phenylethylsulfanyl)pyran-2-yl]phenoxy]acetate Chemical compound CCOC(=O)COC1=CC=CC(C=2OC(=O)C(SCCC=3C=CC=CC=3)=C(O)C=2)=C1 ACTFWSGUDLQVRL-UHFFFAOYSA-N 0.000 description 1
- GXGWROGCAHSCDT-UHFFFAOYSA-N ethyl 2-[4-[4-hydroxy-6-oxo-5-(2-propan-2-ylphenyl)sulfanylpyran-2-yl]phenoxy]acetate Chemical compound C1=CC(OCC(=O)OCC)=CC=C1C(OC1=O)=CC(O)=C1SC1=CC=CC=C1C(C)C GXGWROGCAHSCDT-UHFFFAOYSA-N 0.000 description 1
- CNIADBGSPDCKLS-UHFFFAOYSA-N ethyl 2-benzyl-3-ethoxy-3-sulfanylidenepropanoate Chemical compound CCOC(=O)C(C(=S)OCC)CC1=CC=CC=C1 CNIADBGSPDCKLS-UHFFFAOYSA-N 0.000 description 1
- GLOAPLPTWAXAIG-UHFFFAOYSA-N ethyl 4-acetylbenzoate Chemical compound CCOC(=O)C1=CC=C(C(C)=O)C=C1 GLOAPLPTWAXAIG-UHFFFAOYSA-N 0.000 description 1
- 230000003203 everyday effect Effects 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000003818 flash chromatography 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
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 208000001130 gallstones Diseases 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 244000000059 gram-positive pathogen Species 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000006277 halobenzyl group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005059 halophenyl group Chemical group 0.000 description 1
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 208000033519 human immunodeficiency virus infectious disease Diseases 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- FZOUYFUXCFJIBH-UHFFFAOYSA-N hydroxy-(4-methyl-2-phenyl-3-prop-1-enylphenyl)-oxo-sulfanylidene-lambda6-sulfane Chemical compound CC=CC1=C(C)C=CC(S(O)(=O)=S)=C1C1=CC=CC=C1 FZOUYFUXCFJIBH-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000007813 immunodeficiency Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- SNHMUERNLJLMHN-UHFFFAOYSA-N iodobenzene Chemical compound IC1=CC=CC=C1 SNHMUERNLJLMHN-UHFFFAOYSA-N 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- ISVMGSYGCXYTNL-UHFFFAOYSA-N methyl 2-(4-acetylphenoxy)acetate Chemical compound COC(=O)COC1=CC=C(C(C)=O)C=C1 ISVMGSYGCXYTNL-UHFFFAOYSA-N 0.000 description 1
- KIJXOTJDPUGJSX-UHFFFAOYSA-N methyl 2-[(4-acetylphenoxy)methyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1COC1=CC=C(C(C)=O)C=C1 KIJXOTJDPUGJSX-UHFFFAOYSA-N 0.000 description 1
- BBIGCTLIYRLOHO-UHFFFAOYSA-N methyl 2-[(4-methylphenyl)sulfonothioyloxymethyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1COS(=O)(=S)C1=CC=C(C)C=C1 BBIGCTLIYRLOHO-UHFFFAOYSA-N 0.000 description 1
- YDCHPLOFQATIDS-UHFFFAOYSA-N methyl 2-bromoacetate Chemical compound COC(=O)CBr YDCHPLOFQATIDS-UHFFFAOYSA-N 0.000 description 1
- WMMXUAVVJIGEJW-UHFFFAOYSA-N methyl 3-[(4-acetylphenoxy)methyl]benzoate Chemical compound COC(=O)C1=CC=CC(COC=2C=CC(=CC=2)C(C)=O)=C1 WMMXUAVVJIGEJW-UHFFFAOYSA-N 0.000 description 1
- JZOSCTVIJMKEOM-UHFFFAOYSA-N methyl 3-[(4-hydroxy-2-oxo-6-phenylpyran-3-yl)sulfanylmethyl]benzoate Chemical compound COC(=O)C1=CC=CC(CSC=2C(OC(=CC=2O)C=2C=CC=CC=2)=O)=C1 JZOSCTVIJMKEOM-UHFFFAOYSA-N 0.000 description 1
- KPQCDOUQBBIWGJ-UHFFFAOYSA-N methyl 3-[(4-methylphenyl)sulfonothioyloxymethyl]benzoate Chemical compound COC(=O)C1=CC=CC(COS(=O)(=S)C=2C=CC(C)=CC=2)=C1 KPQCDOUQBBIWGJ-UHFFFAOYSA-N 0.000 description 1
- GWKOSWCUFMNCMK-UHFFFAOYSA-N methyl 4-[(4-acetylphenoxy)methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1COC1=CC=C(C(C)=O)C=C1 GWKOSWCUFMNCMK-UHFFFAOYSA-N 0.000 description 1
- ATCBDXYOSWJKFZ-UHFFFAOYSA-N methyl 4-[(4-hydroxy-2-oxo-6-phenylpyran-3-yl)sulfanylmethyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CSC1=C(O)C=C(C=2C=CC=CC=2)OC1=O ATCBDXYOSWJKFZ-UHFFFAOYSA-N 0.000 description 1
- UWWWWGFYATXUDL-UHFFFAOYSA-N methyl 4-[[4-[4-hydroxy-6-oxo-5-(2-phenylethylsulfanyl)pyran-2-yl]phenoxy]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1COC1=CC=C(C=2OC(=O)C(SCCC=3C=CC=CC=3)=C(O)C=2)C=C1 UWWWWGFYATXUDL-UHFFFAOYSA-N 0.000 description 1
- 238000005497 microtitration Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- KUXXYFOAAQGBAZ-UHFFFAOYSA-N n-(4-hydroxy-2-oxo-6-phenylpyran-3-yl)-2-phenylacetamide Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1NC(=O)CC1=CC=CC=C1 KUXXYFOAAQGBAZ-UHFFFAOYSA-N 0.000 description 1
- DARMKZFEJWAOCA-UHFFFAOYSA-N n-(4-hydroxy-2-oxo-6-phenylpyran-3-yl)-3-phenylpropanamide Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1NC(=O)CCC1=CC=CC=C1 DARMKZFEJWAOCA-UHFFFAOYSA-N 0.000 description 1
- KLJPNLDBQJLOBD-UHFFFAOYSA-N n-(4-hydroxy-2-oxo-6-phenylpyran-3-yl)naphthalene-2-carboxamide Chemical compound O1C(=O)C(NC(=O)C=2C=C3C=CC=CC3=CC=2)=C(O)C=C1C1=CC=CC=C1 KLJPNLDBQJLOBD-UHFFFAOYSA-N 0.000 description 1
- ZFDKDYYANATUTD-UHFFFAOYSA-N n-[3-[4-hydroxy-6-oxo-5-(2-phenylethylsulfanyl)pyran-2-yl]phenyl]-4-methylbenzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC1=CC=CC(C=2OC(=O)C(SCCC=3C=CC=CC=3)=C(O)C=2)=C1 ZFDKDYYANATUTD-UHFFFAOYSA-N 0.000 description 1
- DOTIDSAFRBMVCY-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-2-oxo-6-(2-phenylpropan-2-yl)pyran-3-yl]methyl]phenyl]benzenesulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3C=CC=CC=3)C=CC=2)C(=O)OC=1C(C)(C)C1=CC=CC=C1 DOTIDSAFRBMVCY-UHFFFAOYSA-N 0.000 description 1
- HDTHCFZFLUTAAY-UHFFFAOYSA-N n-[4-[4-hydroxy-6-oxo-5-(2-phenylethylsulfanyl)pyran-2-yl]phenyl]benzenesulfonamide Chemical compound OC=1C=C(C=2C=CC(NS(=O)(=O)C=3C=CC=CC=3)=CC=2)OC(=O)C=1SCCC1=CC=CC=C1 HDTHCFZFLUTAAY-UHFFFAOYSA-N 0.000 description 1
- NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 229920003052 natural elastomer Polymers 0.000 description 1
- 229920001194 natural rubber Polymers 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-M phenoxyacetate Chemical compound [O-]C(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-M 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 230000001323 posttranslational effect Effects 0.000 description 1
- RUDNWZFWWJFUSF-UHFFFAOYSA-M potassium;(4-methylphenyl)-oxido-oxo-sulfanylidene-$l^{6}-sulfane Chemical compound [K+].CC1=CC=C(S([O-])(=O)=S)C=C1 RUDNWZFWWJFUSF-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 238000002976 reverse transcriptase assay Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
- 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 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 229920003051 synthetic elastomer Polymers 0.000 description 1
- 239000005061 synthetic rubber Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000004001 thioalkyl group Chemical group 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000007070 tosylation reaction Methods 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
- BWHOZHOGCMHOBV-BQYQJAHWSA-N trans-benzylideneacetone Chemical compound CC(=O)\C=C\C1=CC=CC=C1 BWHOZHOGCMHOBV-BQYQJAHWSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 244000052613 viral pathogen Species 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/02—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15502893A | 1993-11-19 | 1993-11-19 | |
US08/319,769 US6005103A (en) | 1993-11-19 | 1994-10-12 | Pyrone derivatives as protease inhibitors and antiviral agents |
PCT/US1994/012257 WO1995014013A1 (en) | 1993-11-19 | 1994-10-26 | Pyrone derivatives as protease inhibitors and antiviral agents |
Publications (3)
Publication Number | Publication Date |
---|---|
NO962016D0 NO962016D0 (no) | 1996-05-15 |
NO962016L NO962016L (no) | 1996-05-15 |
NO315747B1 true NO315747B1 (no) | 2003-10-20 |
Family
ID=26851949
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19962016A NO315747B1 (no) | 1993-11-19 | 1996-05-15 | Pyronderivater, anvendelse derav, samt farmasöytisk preparat |
Country Status (16)
Country | Link |
---|---|
EP (1) | EP0729465B1 (de) |
JP (1) | JPH09505293A (de) |
AT (1) | ATE231502T1 (de) |
AU (1) | AU687465B2 (de) |
CA (1) | CA2176044A1 (de) |
DE (1) | DE69432056T2 (de) |
DK (1) | DK0729465T3 (de) |
ES (1) | ES2191035T3 (de) |
FI (1) | FI962020A (de) |
HR (1) | HRP940939B1 (de) |
HU (1) | HUT77719A (de) |
IL (1) | IL111672A0 (de) |
NO (1) | NO315747B1 (de) |
NZ (1) | NZ275325A (de) |
PT (1) | PT729465E (de) |
WO (1) | WO1995014013A1 (de) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1173947C (zh) | 1995-06-28 | 2004-11-03 | 拜尔公司 | 2,4,5-三取代的苯基酮烯醇作为农药和除草剂的应用 |
DE10016544A1 (de) * | 2000-04-03 | 2001-10-11 | Bayer Ag | C2-phenylsubstituierte Ketoenole |
DE10142663B4 (de) | 2001-08-31 | 2004-08-19 | Aventis Pharma Deutschland Gmbh | C2-Disubstituierte Indan-1-ol-Systeme |
KR101122708B1 (ko) | 2003-12-26 | 2012-03-26 | 마사토시 하기와라 | Sr 단백질 인산화 제어 방법, 및 유효성분으로서 sr 단백질 활성 제어제를 함유하는 항바이러스제 |
CN114075161B (zh) * | 2020-08-21 | 2023-01-31 | 扬州大学附属医院 | 一种用于治疗呼吸道疾病的α-吡喃酮类化合物的制备方法 |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3277088A (en) * | 1963-10-03 | 1966-10-04 | Eastman Kodak Co | 4-(tertiaryamino)-2h-pyran-2-ones |
FR3724M (fr) * | 1963-12-04 | 1965-12-06 | Marcel Perrault | Médicament a base d'anisoyl-3 hydroxy-4 p. méthoxy-phényl-6α-pyrone. |
DE4308451A1 (de) * | 1992-09-10 | 1994-04-14 | Bayer Ag | 3-Aryl-pyron-Derivate |
ZA938019B (en) * | 1992-11-13 | 1995-04-28 | Upjohn Co | Pyran-2-ones and 5,6-dihydropyran-2-ones useful for treating HIV and other retroviruses |
-
1994
- 1994-10-26 NZ NZ275325A patent/NZ275325A/xx unknown
- 1994-10-26 WO PCT/US1994/012257 patent/WO1995014013A1/en active IP Right Grant
- 1994-10-26 PT PT94932042T patent/PT729465E/pt unknown
- 1994-10-26 EP EP94932042A patent/EP0729465B1/de not_active Expired - Lifetime
- 1994-10-26 AT AT94932042T patent/ATE231502T1/de not_active IP Right Cessation
- 1994-10-26 ES ES94932042T patent/ES2191035T3/es not_active Expired - Lifetime
- 1994-10-26 JP JP7514457A patent/JPH09505293A/ja active Pending
- 1994-10-26 DK DK94932042T patent/DK0729465T3/da active
- 1994-10-26 HU HU9601350A patent/HUT77719A/hu unknown
- 1994-10-26 AU AU80911/94A patent/AU687465B2/en not_active Ceased
- 1994-10-26 CA CA002176044A patent/CA2176044A1/en not_active Abandoned
- 1994-10-26 DE DE69432056T patent/DE69432056T2/de not_active Expired - Fee Related
- 1994-11-17 IL IL11167294A patent/IL111672A0/xx unknown
- 1994-11-18 HR HR940939A patent/HRP940939B1/xx not_active IP Right Cessation
-
1996
- 1996-05-13 FI FI962020A patent/FI962020A/fi unknown
- 1996-05-15 NO NO19962016A patent/NO315747B1/no not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
EP0729465A1 (de) | 1996-09-04 |
FI962020A (fi) | 1996-05-31 |
HU9601350D0 (en) | 1996-07-29 |
EP0729465B1 (de) | 2003-01-22 |
WO1995014013A1 (en) | 1995-05-26 |
ATE231502T1 (de) | 2003-02-15 |
ES2191035T3 (es) | 2003-09-01 |
NO962016D0 (no) | 1996-05-15 |
AU687465B2 (en) | 1998-02-26 |
DE69432056T2 (de) | 2003-10-09 |
PT729465E (pt) | 2003-06-30 |
JPH09505293A (ja) | 1997-05-27 |
HRP940939B1 (en) | 2004-08-31 |
HUT77719A (hu) | 1998-07-28 |
IL111672A0 (en) | 1995-01-24 |
AU8091194A (en) | 1995-06-06 |
NZ275325A (en) | 1999-08-30 |
NO962016L (no) | 1996-05-15 |
FI962020A0 (fi) | 1996-05-13 |
CA2176044A1 (en) | 1995-05-26 |
DK0729465T3 (da) | 2003-04-22 |
DE69432056D1 (de) | 2003-02-27 |
HRP940939A2 (en) | 1997-06-30 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US6005103A (en) | Pyrone derivatives as protease inhibitors and antiviral agents | |
JP3684426B2 (ja) | プロテアーゼ阻害剤および抗ウイルス剤としての5,6−ジヒドロピロン誘導体 | |
SK284407B6 (sk) | Pyranónové zlúčeniny na použitie na liečenie retrovírusových infekcií | |
JP3698435B2 (ja) | プロテアーゼ阻害剤および抗ウイルス剤としての5,6−ジヒドロピロン誘導体 | |
US5789440A (en) | 5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents | |
NO315747B1 (no) | Pyronderivater, anvendelse derav, samt farmasöytisk preparat | |
AU682417B2 (en) | Pyrone derivatives as protease inhibitors and antiviral agents | |
KR100441361B1 (ko) | 프로테아제억제제및항바이러스제로서의5,6-디히드로피론유도체 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM1K | Lapsed by not paying the annual fees |