NO315117B1 - 5,6-dihydropyron-derivater og farmasöytiske preparat for behandling av infeksjon eller sykdom forårsaket av en bakterie eller et retrovirus - Google Patents
5,6-dihydropyron-derivater og farmasöytiske preparat for behandling av infeksjon eller sykdom forårsaket av en bakterie eller et retrovirus Download PDFInfo
- Publication number
- NO315117B1 NO315117B1 NO19962018A NO962018A NO315117B1 NO 315117 B1 NO315117 B1 NO 315117B1 NO 19962018 A NO19962018 A NO 19962018A NO 962018 A NO962018 A NO 962018A NO 315117 B1 NO315117 B1 NO 315117B1
- Authority
- NO
- Norway
- Prior art keywords
- dihydro
- hydroxy
- pyran
- phenyl
- thio
- Prior art date
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- 238000011282 treatment Methods 0.000 title claims abstract description 22
- 201000010099 disease Diseases 0.000 title claims abstract description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims abstract description 11
- 208000015181 infectious disease Diseases 0.000 title claims description 17
- 241001430294 unidentified retrovirus Species 0.000 title claims description 14
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 6
- 241000894006 Bacteria Species 0.000 title claims description 3
- QBDAFARLDLCWAT-UHFFFAOYSA-N 2,3-dihydropyran-6-one Chemical class O=C1OCCC=C1 QBDAFARLDLCWAT-UHFFFAOYSA-N 0.000 title abstract description 25
- 150000001875 compounds Chemical class 0.000 claims description 267
- -1 2-isopropylphenyl Chemical group 0.000 claims description 118
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 57
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 49
- 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 30
- 229960000583 acetic acid Drugs 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 12
- 239000004305 biphenyl Substances 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- ADSZRVGJNUXBQB-UHFFFAOYSA-N 5-bromo-4-hydroxy-2-phenyl-2-(2-phenylethyl)-3h-pyran-6-one Chemical compound C1C(O)=C(Br)C(=O)OC1(C=1C=CC=CC=1)CCC1=CC=CC=C1 ADSZRVGJNUXBQB-UHFFFAOYSA-N 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- PQOFOXIQCWOYFL-UHFFFAOYSA-N 5-(4-hydroxy-6-oxo-2-phenyl-3h-pyran-2-yl)pentanoic acid Chemical compound C=1C=CC=CC=1C1(CCCCC(=O)O)CC(O)=CC(=O)O1 PQOFOXIQCWOYFL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- LUQSZGJFVAYSEF-UHFFFAOYSA-N 2-(cyclopentylmethyl)-4-hydroxy-2-phenyl-3h-pyran-6-one Chemical compound C1C(O)=CC(=O)OC1(C=1C=CC=CC=1)CC1CCCC1 LUQSZGJFVAYSEF-UHFFFAOYSA-N 0.000 claims description 6
- 101100516554 Caenorhabditis elegans nhr-5 gene Proteins 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- PLGNLGVFOGRRRP-UHFFFAOYSA-N 2-[2-(1,3-benzodioxol-5-yl)ethyl]-4-hydroxy-2-phenyl-3h-pyran-6-one Chemical compound C1C(O)=CC(=O)OC1(C=1C=CC=CC=1)CCC1=CC=C(OCO2)C2=C1 PLGNLGVFOGRRRP-UHFFFAOYSA-N 0.000 claims description 4
- AHMHROWQGBYDDY-UHFFFAOYSA-N 5-(5-bromo-4-hydroxy-6-oxo-2-phenyl-3h-pyran-2-yl)pentanoic acid Chemical compound C=1C=CC=CC=1C1(CCCCC(=O)O)CC(O)=C(Br)C(=O)O1 AHMHROWQGBYDDY-UHFFFAOYSA-N 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
- QPEREQJMHPQPDP-UHFFFAOYSA-N 2-(4-methylsulfanylphenyl)-5-(2-phenylethylsulfanyl)-2,3-dihydropyran-6-one Chemical compound C1=CC(SC)=CC=C1C1OC(=O)C(SCCC=2C=CC=CC=2)=CC1 QPEREQJMHPQPDP-UHFFFAOYSA-N 0.000 claims description 3
- ZROLIMSFDJMZMG-UHFFFAOYSA-N 2-phenyl-2-(2-phenylethyl)-3h-pyran-6-one Chemical compound C1C=CC(=O)OC1(C=1C=CC=CC=1)CCC1=CC=CC=C1 ZROLIMSFDJMZMG-UHFFFAOYSA-N 0.000 claims description 3
- SKFLRFBMDZILLG-UHFFFAOYSA-N 3-benzylsulfanyl-6-phenyl-6-propyloxane-2,4-dione Chemical compound CCCC1(CC(=O)C(SCc2ccccc2)C(=O)O1)c1ccccc1 SKFLRFBMDZILLG-UHFFFAOYSA-N 0.000 claims description 3
- IAJHQEPVRWITPY-UHFFFAOYSA-N 4-hydroxy-2-(3-methylphenyl)-5-(2-phenylethylsulfanyl)-2,3-dihydropyran-6-one Chemical compound CC1=CC=CC(C2OC(=O)C(SCCC=3C=CC=CC=3)=C(O)C2)=C1 IAJHQEPVRWITPY-UHFFFAOYSA-N 0.000 claims description 3
- FOQVFVMXNYSPJX-UHFFFAOYSA-N 4-hydroxy-5-(5-methyl-2-propan-2-ylphenyl)sulfanyl-2-phenyl-2,3-dihydro-1h-pyridin-6-one Chemical compound CC(C)C1=CC=C(C)C=C1SC1=C(O)CC(C=2C=CC=CC=2)NC1=O FOQVFVMXNYSPJX-UHFFFAOYSA-N 0.000 claims description 3
- YLGHVFFSHBLCIP-UHFFFAOYSA-N 5-(2-phenylethylsulfanyl)-2-(4-phenylmethoxyphenyl)-2,3-dihydropyran-6-one Chemical compound O=C1OC(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)CC=C1SCCC1=CC=CC=C1 YLGHVFFSHBLCIP-UHFFFAOYSA-N 0.000 claims description 3
- IGXADARJEZABME-UHFFFAOYSA-N 5-(3-chlorophenyl)-2-(2-phenylethylsulfanyl)cyclohexane-1,3-dione Chemical compound ClC1=CC=CC(C2CC(=O)C(SCCC=3C=CC=CC=3)C(=O)C2)=C1 IGXADARJEZABME-UHFFFAOYSA-N 0.000 claims description 3
- AZBJRELDDRKLRH-UHFFFAOYSA-N 5-bromo-4-hydroxy-3-(3-methylbutyl)-2-phenyl-2,3-dihydropyran-6-one Chemical compound O1C(=O)C(Br)=C(O)C(CCC(C)C)C1C1=CC=CC=C1 AZBJRELDDRKLRH-UHFFFAOYSA-N 0.000 claims description 3
- RXSSTHJXYIXSFF-UHFFFAOYSA-N 6-pentyl-6-phenyl-3-(2-phenylethylsulfanyl)oxane-2,4-dione Chemical compound CCCCCC1(CC(=O)C(SCCc2ccccc2)C(=O)O1)c1ccccc1 RXSSTHJXYIXSFF-UHFFFAOYSA-N 0.000 claims description 3
- HCFFAIZSNVOHSY-UHFFFAOYSA-N 6-phenyl-3-(2-phenylethylsulfanyl)-6-propyloxane-2,4-dione Chemical compound CCCC1(CC(=O)C(SCCc2ccccc2)C(=O)O1)c1ccccc1 HCFFAIZSNVOHSY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- YQRASQZNBACISH-UHFFFAOYSA-N 1-benzyl-3-[3-[4-hydroxy-6-oxo-2-phenyl-5-(2-propan-2-ylphenyl)sulfanyl-3h-pyran-2-yl]propyl]urea Chemical compound CC(C)C1=CC=CC=C1SC(C(O1)=O)=C(O)CC1(C=1C=CC=CC=1)CCCNC(=O)NCC1=CC=CC=C1 YQRASQZNBACISH-UHFFFAOYSA-N 0.000 claims description 2
- RFTCEFMEOZCGQW-UHFFFAOYSA-N 2-(cyclopenten-1-yl)benzenethiol Chemical compound SC1=CC=CC=C1C1=CCCC1 RFTCEFMEOZCGQW-UHFFFAOYSA-N 0.000 claims description 2
- BNSOAHLFCNDUDM-UHFFFAOYSA-N 2-[2-(1,3-benzodioxol-5-yl)ethyl]-5-bromo-4-hydroxy-2-phenyl-3h-pyran-6-one Chemical compound C1C(O)=C(Br)C(=O)OC1(C=1C=CC=CC=1)CCC1=CC=C(OCO2)C2=C1 BNSOAHLFCNDUDM-UHFFFAOYSA-N 0.000 claims description 2
- YXLUMCQVYQCIPZ-UHFFFAOYSA-N 2-[4-(5-benzylsulfanyl-4-hydroxy-6-oxo-2,3-dihydropyran-2-yl)phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1C1OC(=O)C(SCC=2C=CC=CC=2)=C(O)C1 YXLUMCQVYQCIPZ-UHFFFAOYSA-N 0.000 claims description 2
- BJKHBHGRLZMQOM-UHFFFAOYSA-N 2-[4-[4-hydroxy-6-oxo-5-(2-phenylethylsulfanyl)-2,3-dihydropyran-2-yl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1C1OC(=O)C(SCCC=2C=CC=CC=2)=C(O)C1 BJKHBHGRLZMQOM-UHFFFAOYSA-N 0.000 claims description 2
- XXXFHKLKFZFOKC-UHFFFAOYSA-N 2-[5-(5-methyl-2-propan-2-ylphenyl)sulfanyl-6-oxo-2-phenyl-2-(2-phenylethyl)-3H-pyran-4-yl]acetic acid Chemical compound C(C)(C)C1=C(C=C(C=C1)C)SC1=C(CC(OC1=O)(CCC1=CC=CC=C1)C1=CC=CC=C1)CC(=O)O XXXFHKLKFZFOKC-UHFFFAOYSA-N 0.000 claims description 2
- QDQJTYMPFRVUGZ-UHFFFAOYSA-N 2-butyl-4-hydroxy-2-phenyl-5-(2-phenylethylsulfanyl)-3h-pyran-6-one Chemical compound O=C1OC(CCCC)(C=2C=CC=CC=2)CC(O)=C1SCCC1=CC=CC=C1 QDQJTYMPFRVUGZ-UHFFFAOYSA-N 0.000 claims description 2
- WPPQBTYILCYIQV-UHFFFAOYSA-N 2-butyl-5-(1-ethylindol-3-yl)sulfanyl-4-hydroxy-2-phenyl-3h-pyran-6-one Chemical compound C1C(O)=C(SC=2C3=CC=CC=C3N(CC)C=2)C(=O)OC1(CCCC)C1=CC=CC=C1 WPPQBTYILCYIQV-UHFFFAOYSA-N 0.000 claims description 2
- GGRIFJMWFFDVIA-UHFFFAOYSA-N 2-cyclohexylbenzenethiol Chemical compound SC1=CC=CC=C1C1CCCCC1 GGRIFJMWFFDVIA-UHFFFAOYSA-N 0.000 claims description 2
- VVADIORWEXTPAJ-UHFFFAOYSA-N 2-cyclopentylbenzenethiol Chemical compound SC1=CC=CC=C1C1CCCC1 VVADIORWEXTPAJ-UHFFFAOYSA-N 0.000 claims description 2
- UOPUZOTVOUOBAS-UHFFFAOYSA-N 2-methyl-2-(2-sulfanylphenyl)propan-1-ol Chemical compound OCC(C)(C)C1=CC=CC=C1S UOPUZOTVOUOBAS-UHFFFAOYSA-N 0.000 claims description 2
- KBQRVQZQYCYNIK-UHFFFAOYSA-N 2-tert-butyl-4-methoxybenzenethiol Chemical compound COC1=CC=C(S)C(C(C)(C)C)=C1 KBQRVQZQYCYNIK-UHFFFAOYSA-N 0.000 claims description 2
- OKNQZTHXQTYYQS-UHFFFAOYSA-N 2-tert-butyl-5-methoxybenzenethiol Chemical compound COC1=CC=C(C(C)(C)C)C(S)=C1 OKNQZTHXQTYYQS-UHFFFAOYSA-N 0.000 claims description 2
- YZULKKFQUIFULV-UHFFFAOYSA-N 3-benzylsulfanyl-6,6-diphenyloxane-2,4-dione Chemical compound O=C1CC(C=2C=CC=CC=2)(C=2C=CC=CC=2)OC(=O)C1SCC1=CC=CC=C1 YZULKKFQUIFULV-UHFFFAOYSA-N 0.000 claims description 2
- QIEKVLSEAQCZPM-UHFFFAOYSA-N 3-benzylsulfanyl-6-(3-methylbutyl)-6-phenyloxane-2,4-dione Chemical compound CC(C)CCC1(CC(=O)C(SCc2ccccc2)C(=O)O1)c1ccccc1 QIEKVLSEAQCZPM-UHFFFAOYSA-N 0.000 claims description 2
- UJOCQQAGPAXBKR-UHFFFAOYSA-N 3-benzylsulfanyl-6-pentyl-6-phenyloxane-2,4-dione Chemical compound CCCCCC1(CC(=O)C(SCc2ccccc2)C(=O)O1)c1ccccc1 UJOCQQAGPAXBKR-UHFFFAOYSA-N 0.000 claims description 2
- HPMXNCZSMPSANL-UHFFFAOYSA-N 3-hydroxy-2-(5-methyl-2-propan-2-ylphenyl)sulfanyl-5-phenyl-5-(2-phenylethyl)cyclohex-2-en-1-one Chemical compound CC(C)C1=CC=C(C)C=C1SC(C(C1)=O)=C(O)CC1(C=1C=CC=CC=1)CCC1=CC=CC=C1 HPMXNCZSMPSANL-UHFFFAOYSA-N 0.000 claims description 2
- DPEJDFKJNRBYCE-UHFFFAOYSA-N 3-methoxy-2-propan-2-ylbenzenethiol Chemical compound COC1=CC=CC(S)=C1C(C)C DPEJDFKJNRBYCE-UHFFFAOYSA-N 0.000 claims description 2
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- SUJDAWCJKCXJJD-UHFFFAOYSA-N 4-(5-benzylsulfanyl-4-hydroxy-6-oxo-2,3-dihydropyran-2-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1OC(=O)C(SCC=2C=CC=CC=2)=C(O)C1 SUJDAWCJKCXJJD-UHFFFAOYSA-N 0.000 claims description 2
- XWYNTHSKVLJNCF-UHFFFAOYSA-N 4-hydroxy-1-methyl-2-phenyl-5-(2-phenylethylsulfanyl)-2,3-dihydropyridin-6-one Chemical compound O=C1N(C)C(C=2C=CC=CC=2)CC(O)=C1SCCC1=CC=CC=C1 XWYNTHSKVLJNCF-UHFFFAOYSA-N 0.000 claims description 2
- UVWRSAMQDGORIB-UHFFFAOYSA-N 4-hydroxy-2-(2-morpholin-4-ylethyl)-2-phenyl-5-(2-propan-2-ylphenyl)sulfanyl-3h-pyran-6-one Chemical compound CC(C)C1=CC=CC=C1SC(C(O1)=O)=C(O)CC1(C=1C=CC=CC=1)CCN1CCOCC1 UVWRSAMQDGORIB-UHFFFAOYSA-N 0.000 claims description 2
- JOXADRUOZIJHHL-UHFFFAOYSA-N 4-hydroxy-2-(3-morpholin-4-ylpropyl)-2-phenyl-5-(2-propan-2-ylphenyl)sulfanyl-3h-pyran-6-one Chemical compound CC(C)C1=CC=CC=C1SC(C(O1)=O)=C(O)CC1(C=1C=CC=CC=1)CCCN1CCOCC1 JOXADRUOZIJHHL-UHFFFAOYSA-N 0.000 claims description 2
- NYJKCYONHMEBFH-UHFFFAOYSA-N 4-hydroxy-2-(3-oxo-3-piperazin-1-ylpropyl)-2-phenyl-5-(2-propan-2-ylphenyl)sulfanyl-3h-pyran-6-one Chemical compound CC(C)C1=CC=CC=C1SC(C(O1)=O)=C(O)CC1(C=1C=CC=CC=1)CCC(=O)N1CCNCC1 NYJKCYONHMEBFH-UHFFFAOYSA-N 0.000 claims description 2
- AFFFNZLDPHASEM-UHFFFAOYSA-N 4-hydroxy-2-(4-hydroxyphenyl)-5-(2-phenylethylsulfanyl)-2,3-dihydropyran-6-one Chemical compound O=C1OC(C=2C=CC(O)=CC=2)CC(O)=C1SCCC1=CC=CC=C1 AFFFNZLDPHASEM-UHFFFAOYSA-N 0.000 claims description 2
- YLBHZSISDFFGAH-UHFFFAOYSA-N 4-hydroxy-2-(4-morpholin-4-ylbutyl)-2-phenyl-5-(2-propan-2-ylphenyl)sulfanyl-3h-pyran-6-one Chemical compound CC(C)C1=CC=CC=C1SC(C(O1)=O)=C(O)CC1(C=1C=CC=CC=1)CCCCN1CCOCC1 YLBHZSISDFFGAH-UHFFFAOYSA-N 0.000 claims description 2
- MGZJJNVSPNATLS-UHFFFAOYSA-N 4-hydroxy-2-(4-oxo-4-piperazin-1-ylbutyl)-2-phenyl-5-(2-propan-2-ylphenyl)sulfanyl-3h-pyran-6-one Chemical compound CC(C)C1=CC=CC=C1SC(C(O1)=O)=C(O)CC1(C=1C=CC=CC=1)CCCC(=O)N1CCNCC1 MGZJJNVSPNATLS-UHFFFAOYSA-N 0.000 claims description 2
- UBHSTAHPYULXSI-UHFFFAOYSA-N 4-hydroxy-2-(4-oxo-4-thiomorpholin-4-ylbutyl)-2-phenyl-5-(2-propan-2-ylphenyl)sulfanyl-3h-pyran-6-one Chemical compound CC(C)C1=CC=CC=C1SC(C(O1)=O)=C(O)CC1(C=1C=CC=CC=1)CCCC(=O)N1CCSCC1 UBHSTAHPYULXSI-UHFFFAOYSA-N 0.000 claims description 2
- OCMPUUYBDHNZCQ-UHFFFAOYSA-N 4-hydroxy-2-(5-oxo-5-piperazin-1-ylpentyl)-2-phenyl-5-(2-propan-2-ylphenyl)sulfanyl-3h-pyran-6-one Chemical compound CC(C)C1=CC=CC=C1SC(C(O1)=O)=C(O)CC1(C=1C=CC=CC=1)CCCCC(=O)N1CCNCC1 OCMPUUYBDHNZCQ-UHFFFAOYSA-N 0.000 claims description 2
- REAKAGIAIPTKIS-UHFFFAOYSA-N 4-hydroxy-2-[2-(1h-indol-5-yl)ethyl]-5-(5-methyl-2-propan-2-ylphenyl)sulfanyl-2-phenyl-3h-pyran-6-one Chemical compound CC(C)C1=CC=C(C)C=C1SC(C(O1)=O)=C(O)CC1(C=1C=CC=CC=1)CCC1=CC=C(NC=C2)C2=C1 REAKAGIAIPTKIS-UHFFFAOYSA-N 0.000 claims description 2
- UJVLEZAOOXMFOV-UHFFFAOYSA-N 4-hydroxy-2-[4-(2-morpholin-4-ylethoxy)phenyl]-2-(2-phenylethyl)-5-(2-phenylethylsulfanyl)-3h-pyran-6-one Chemical compound O=C1OC(CCC=2C=CC=CC=2)(C=2C=CC(OCCN3CCOCC3)=CC=2)CC(O)=C1SCCC1=CC=CC=C1 UJVLEZAOOXMFOV-UHFFFAOYSA-N 0.000 claims description 2
- JJZNLATWATWDDW-UHFFFAOYSA-N 4-hydroxy-2-[5-(4-methylpiperazin-1-yl)-5-oxopentyl]-2-phenyl-5-(2-propan-2-ylphenyl)sulfanyl-3h-pyran-6-one Chemical compound CC(C)C1=CC=CC=C1SC(C(O1)=O)=C(O)CC1(C=1C=CC=CC=1)CCCCC(=O)N1CCN(C)CC1 JJZNLATWATWDDW-UHFFFAOYSA-N 0.000 claims description 2
- AHSLQWTWSDEDME-UHFFFAOYSA-N 4-hydroxy-2-phenyl-2-(4-piperazin-1-ylbutyl)-5-(2-propan-2-ylphenyl)sulfanyl-3h-pyran-6-one Chemical compound CC(C)C1=CC=CC=C1SC(C(O1)=O)=C(O)CC1(C=1C=CC=CC=1)CCCCN1CCNCC1 AHSLQWTWSDEDME-UHFFFAOYSA-N 0.000 claims description 2
- XJBMVRDGASDGNN-UHFFFAOYSA-N 4-hydroxy-2-phenyl-5-(2-phenylethylsulfanyl)-2,3-dihydro-1h-pyridin-6-one Chemical compound O=C1NC(C=2C=CC=CC=2)CC(O)=C1SCCC1=CC=CC=C1 XJBMVRDGASDGNN-UHFFFAOYSA-N 0.000 claims description 2
- OZUQVUGCZCPFBQ-UHFFFAOYSA-N 4-hydroxy-2-phenyl-5-(2-phenylethylsulfanyl)-2-(2-piperazin-1-ylethyl)-3h-pyran-6-one Chemical compound O=C1OC(CCN2CCNCC2)(C=2C=CC=CC=2)CC(O)=C1SCCC1=CC=CC=C1 OZUQVUGCZCPFBQ-UHFFFAOYSA-N 0.000 claims description 2
- LBAKUXFGOVAFHO-UHFFFAOYSA-N 4-hydroxy-5-(5-methyl-2-propan-2-ylphenyl)sulfanyl-2-phenyl-2-(2-phenylethyl)-1,3-dihydropyridin-6-one Chemical compound CC(C)C1=CC=C(C)C=C1SC(C(N1)=O)=C(O)CC1(C=1C=CC=CC=1)CCC1=CC=CC=C1 LBAKUXFGOVAFHO-UHFFFAOYSA-N 0.000 claims description 2
- REDHSOYAHPEIHF-UHFFFAOYSA-N 5-(2-tert-butylfuran-3-yl)sulfanyl-4-hydroxy-2-phenyl-2-(2-phenylethyl)-3h-pyran-6-one Chemical compound O1C=CC(SC=2C(OC(CCC=3C=CC=CC=3)(CC=2O)C=2C=CC=CC=2)=O)=C1C(C)(C)C REDHSOYAHPEIHF-UHFFFAOYSA-N 0.000 claims description 2
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- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- SKFLCXNDKRUHTA-UHFFFAOYSA-N phenyl(pyridin-4-yl)methanone Chemical compound C=1C=NC=CC=1C(=O)C1=CC=CC=C1 SKFLCXNDKRUHTA-UHFFFAOYSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 description 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 1
- 230000001323 posttranslational effect Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical group 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 230000017854 proteolysis Effects 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- MERGMNQXULKBCH-UHFFFAOYSA-N pyran-2,4-dione Chemical class O=C1CC(=O)C=CO1 MERGMNQXULKBCH-UHFFFAOYSA-N 0.000 description 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
- 125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
- 125000004941 pyridazin-5-yl group Chemical group N1=NC=CC(=C1)* 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000010076 replication 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
- 238000012552 review Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical group 0.000 description 1
- 238000000926 separation method Methods 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
- 239000002002 slurry Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 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
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000011593 sulfur Substances 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
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- VZQYIWNMSNNNLR-UHFFFAOYSA-N tert-butyl n-[3-[4-hydroxy-6-oxo-2-phenyl-5-(2-propan-2-ylphenyl)sulfanyl-3h-pyran-2-yl]propyl]carbamate Chemical compound CC(C)C1=CC=CC=C1SC1=C(O)CC(CCCNC(=O)OC(C)(C)C)(C=2C=CC=CC=2)OC1=O VZQYIWNMSNNNLR-UHFFFAOYSA-N 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
- 125000003831 tetrazolyl 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
- 125000004001 thioalkyl group Chemical group 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
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- XKGLSKVNOSHTAD-UHFFFAOYSA-N valerophenone Chemical compound CCCCC(=O)C1=CC=CC=C1 XKGLSKVNOSHTAD-UHFFFAOYSA-N 0.000 description 1
- 230000029812 viral genome replication Effects 0.000 description 1
- 244000052613 viral pathogen Species 0.000 description 1
- 239000011345 viscous material Substances 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
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/24—Thiols, sulfides, hydropolysulfides, or polysulfides having thio groups bound to carbon atoms of six-membered aromatic rings
- C07C321/26—Thiols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/80—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D211/84—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/86—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
-
- 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
- C07D407/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Molecular Biology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US15544393A | 1993-11-19 | 1993-11-19 | |
US08/319,821 US5789440A (en) | 1993-11-19 | 1994-10-12 | 5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents |
PCT/US1994/012234 WO1995014011A2 (en) | 1993-11-19 | 1994-10-26 | 5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents |
Publications (3)
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NO962018D0 NO962018D0 (no) | 1996-05-15 |
NO962018L NO962018L (no) | 1996-07-04 |
NO315117B1 true NO315117B1 (no) | 2003-07-14 |
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NO19962018A NO315117B1 (no) | 1993-11-19 | 1996-05-15 | 5,6-dihydropyron-derivater og farmasöytiske preparat for behandling av infeksjon eller sykdom forårsaket av en bakterie eller et retrovirus |
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US (1) | US5936128A (ru) |
EP (1) | EP0729463B1 (ru) |
JP (1) | JP3698435B2 (ru) |
AT (1) | ATE217871T1 (ru) |
AU (1) | AU680064B2 (ru) |
BG (1) | BG63012B1 (ru) |
CA (1) | CA2176041A1 (ru) |
CZ (1) | CZ291856B6 (ru) |
DE (1) | DE69430671T2 (ru) |
DK (1) | DK0729463T3 (ru) |
EE (1) | EE9600045A (ru) |
ES (1) | ES2176263T3 (ru) |
FI (1) | FI962021A (ru) |
HR (1) | HRP940936B1 (ru) |
HU (1) | HUT75225A (ru) |
IL (1) | IL111673A (ru) |
MD (2) | MD1560F2 (ru) |
NO (1) | NO315117B1 (ru) |
NZ (1) | NZ275318A (ru) |
PL (1) | PL180634B1 (ru) |
PT (1) | PT729463E (ru) |
RO (1) | RO117850B1 (ru) |
RU (1) | RU2160733C2 (ru) |
SI (1) | SI0729463T1 (ru) |
SK (1) | SK283240B6 (ru) |
TJ (1) | TJ320B (ru) |
WO (1) | WO1995014011A2 (ru) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1997014812A2 (en) * | 1995-10-16 | 1997-04-24 | Chiron Corporation | Method of screening for factors that modulate gene expression |
DE69634959T2 (de) | 1995-11-13 | 2006-05-24 | Vitaleech Bioscience N.V. | Antivirale isolate von blutegeln |
US5834506A (en) * | 1996-11-01 | 1998-11-10 | Warner-Lambert Company | Dihydropyrones with improved antiviral activity |
US6087455A (en) * | 1997-12-19 | 2000-07-11 | Shell Oil Company | Process for hydrogenation of macromolecular organic substrates |
BR9913598A (pt) | 1998-09-11 | 2001-05-29 | Warner Lambert Co | Inibidores de protease de hiv |
DE10030094A1 (de) | 2000-06-19 | 2001-12-20 | Bayer Ag | Phenylsubstituierte 5,6-Dihydro-pyron-Derivate |
DE10100175A1 (de) * | 2001-01-04 | 2002-07-11 | Bayer Ag | Hetarylsubstituierte Homotetram-und Homotetronsäuren |
DOP2003000641A (es) | 2002-05-10 | 2003-11-15 | Pfizer | Inhibidores de las arn polimerasa dependiente de arn del virus de las hepatitis c y composiciones y tratamiento que los usan |
US7148226B2 (en) | 2003-02-21 | 2006-12-12 | Agouron Pharmaceuticals, Inc. | Inhibitors of hepatitis C virus RNA-dependent RNA polymerase, and compositions and treatments using the same |
WO2006018725A1 (en) | 2004-08-18 | 2006-02-23 | Pfizer Inc. | Inhibitors of hepatitis c virus rna-dependent rna polymerase, and compositions and treatments using the same |
US9012471B2 (en) * | 2008-04-11 | 2015-04-21 | The Trustees Of Columbia University In The City Of New York | Glucose metabolism modulating compounds |
EP3068416A4 (en) | 2013-11-11 | 2017-08-09 | Kuality Herbceutics LLC | Kava derived therapeutic compounds and methods of use thereof |
US10584108B2 (en) | 2015-05-07 | 2020-03-10 | Kuality Herbceutics Llc | Therapeutic compounds and methods of use thereof |
US10889565B2 (en) * | 2016-06-14 | 2021-01-12 | Bristol-Myers Squibb Company | 4-hydroxy-3-sulfonylpyridin-2(1H)-ones as APJ receptor agonists |
CA3039853A1 (en) | 2016-10-17 | 2018-04-26 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
GB201707856D0 (en) | 2017-05-16 | 2017-06-28 | Arctic Pharma As | Compounds |
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US3206276A (en) * | 1961-09-28 | 1965-09-14 | Minerals Engineering Company | Process for recovery of pure v2o5 from vanadium bearing materials |
US3206476A (en) * | 1962-06-04 | 1965-09-14 | Sterling Drug Inc | 3-substituted-4-hydroxy-6-aryl-2-pyrones and preparation |
US3931235A (en) * | 1972-12-18 | 1976-01-06 | The Dow Chemical Company | Process for preparing sulfur-containing hydroxy pyrones |
US3818046A (en) * | 1972-12-18 | 1974-06-18 | Dow Chemical Co | Sulfur-containing hydroxy pyrones and alkali metal salts thereof |
IL85347A0 (en) * | 1987-02-11 | 1988-07-31 | May & Baker Ltd | Cyclic diones |
AU4074789A (en) * | 1988-03-01 | 1989-09-22 | Upjohn Company, The | Coumarins to inhibit reverse transcriptase in humans |
JPH03227923A (ja) * | 1990-01-30 | 1991-10-08 | Sawai Seiyaku Kk | ひと免疫不全ウイルス疾患処置剤 |
CA2121363A1 (en) * | 1991-11-18 | 1993-05-27 | Mehrdad Badie | User selectable noise cancelling for portable microphones |
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 |
IL108459A0 (en) * | 1993-02-05 | 1994-04-12 | Opjohn Company | 4-Hydroxy-benzopyran-2-ones and 4-hydroxy-cycloalkyl [B] pyran-2-ones useful for treating infections due to hiv and other retroviruses |
-
1994
- 1994-10-26 RO RO96-01015A patent/RO117850B1/ro unknown
- 1994-10-26 EP EP94932030A patent/EP0729463B1/en not_active Expired - Lifetime
- 1994-10-26 EE EE9600045A patent/EE9600045A/xx unknown
- 1994-10-26 SI SI9430417T patent/SI0729463T1/xx unknown
- 1994-10-26 RU RU96113141/04A patent/RU2160733C2/ru not_active IP Right Cessation
- 1994-10-26 CZ CZ19961368A patent/CZ291856B6/cs not_active IP Right Cessation
- 1994-10-26 MD MD96-0172D patent/MD1560F2/xx not_active IP Right Cessation
- 1994-10-26 TJ TJ96000290A patent/TJ320B/xx unknown
- 1994-10-26 JP JP51445495A patent/JP3698435B2/ja not_active Expired - Fee Related
- 1994-10-26 SK SK646-96A patent/SK283240B6/sk unknown
- 1994-10-26 DE DE69430671T patent/DE69430671T2/de not_active Expired - Fee Related
- 1994-10-26 NZ NZ275318A patent/NZ275318A/xx unknown
- 1994-10-26 WO PCT/US1994/012234 patent/WO1995014011A2/en active IP Right Grant
- 1994-10-26 PL PL94314483A patent/PL180634B1/pl not_active IP Right Cessation
- 1994-10-26 DK DK94932030T patent/DK0729463T3/da active
- 1994-10-26 MD MD96-0172A patent/MD1560G2/ru not_active IP Right Cessation
- 1994-10-26 CA CA002176041A patent/CA2176041A1/en not_active Abandoned
- 1994-10-26 HU HU9601349A patent/HUT75225A/hu not_active Application Discontinuation
- 1994-10-26 AU AU80900/94A patent/AU680064B2/en not_active Ceased
- 1994-10-26 PT PT94932030T patent/PT729463E/pt unknown
- 1994-10-26 ES ES94932030T patent/ES2176263T3/es not_active Expired - Lifetime
- 1994-10-26 AT AT94932030T patent/ATE217871T1/de not_active IP Right Cessation
- 1994-11-17 IL IL11167394A patent/IL111673A/xx not_active IP Right Cessation
- 1994-11-17 HR HR940936A patent/HRP940936B1/xx not_active IP Right Cessation
-
1996
- 1996-05-03 BG BG100563A patent/BG63012B1/bg unknown
- 1996-05-13 FI FI962021A patent/FI962021A/fi unknown
- 1996-05-15 NO NO19962018A patent/NO315117B1/no not_active IP Right Cessation
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1998
- 1998-05-15 US US09/079,689 patent/US5936128A/en not_active Expired - Fee Related
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