HRP970571A2 - Dihydropyrones with improved antiviral activity - Google Patents

Dihydropyrones with improved antiviral activity

Info

Publication number: HRP970571A2
Authority: HR; Croatia
Prior art keywords: hydroxy; phenyl; methyl; butyl; tert
Prior art date: 1996-11-01

Application number

HR08/883,743A

Other languages

English (en)

Croatian (hr)

Inventor

Elizabeth Ann Lunney

Original Assignee

Elizabeth Ann Lunney

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1996-11-01

Filing date

1997-10-27

Publication date

1998-08-31

1997-10-27 Application filed by Elizabeth Ann Lunney filed Critical Elizabeth Ann Lunney

1998-08-31 Publication of HRP970571A2 publication Critical patent/HRP970571A2/hr

Links

230000000840 anti-viral effect Effects 0.000 title claims description 19
150000001875 compounds Chemical class 0.000 claims description 280
238000006243 chemical reaction Methods 0.000 claims description 143
-1 5-tert-butyl-4-{4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-methyl-2-oxo-5,6-dihydro-2H- pyran-3-ylsulfanyl}-phenyl ester Chemical class 0.000 claims description 107
239000002253 acid Substances 0.000 claims description 102
150000002148 esters Chemical class 0.000 claims description 85
125000000217 alkyl group Chemical group 0.000 claims description 69
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 66
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
150000002576 ketones Chemical class 0.000 claims description 35
238000000034 method Methods 0.000 claims description 34
125000000623 heterocyclic group Chemical group 0.000 claims description 29
238000002360 preparation method Methods 0.000 claims description 27
125000000753 cycloalkyl group Chemical group 0.000 claims description 26
229910052794 bromium Inorganic materials 0.000 claims description 25
125000005842 heteroatom Chemical group 0.000 claims description 24
229910052757 nitrogen Inorganic materials 0.000 claims description 24
238000011282 treatment Methods 0.000 claims description 23
125000004429 atom Chemical group 0.000 claims description 22
229910052801 chlorine Inorganic materials 0.000 claims description 21
229910052731 fluorine Inorganic materials 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 17
OKIJSNGRQAOIGZ-UHFFFAOYSA-N Butopyronoxyl Chemical compound CCCCOC(=O)C1=CC(=O)CC(C)(C)O1 OKIJSNGRQAOIGZ-UHFFFAOYSA-N 0.000 claims description 14
208000015181 infectious disease Diseases 0.000 claims description 12
NPOWKJDGPQVIJY-UHFFFAOYSA-N 4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-2-methyl-3h-pyran-6-one Chemical compound C=1C=C(O)C=CC=1CCC1(C)CC(O)=CC(=O)O1 NPOWKJDGPQVIJY-UHFFFAOYSA-N 0.000 claims description 11
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
LTXNORXCTHJMSC-UHFFFAOYSA-N 4-hydroxy-2,2-bis[2-(4-hydroxyphenyl)ethyl]-3h-pyran-6-one Chemical compound C1C(O)=CC(=O)OC1(CCC=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 LTXNORXCTHJMSC-UHFFFAOYSA-N 0.000 claims description 10
YGNOYUCUPMACDT-UHFFFAOYSA-N dimethylsulfamic acid Chemical compound CN(C)S(O)(=O)=O YGNOYUCUPMACDT-UHFFFAOYSA-N 0.000 claims description 10
241001430294 unidentified retrovirus Species 0.000 claims description 10
201000010099 disease Diseases 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
SIVVHUQWDOGLJN-UHFFFAOYSA-N ethylsulfamic acid Chemical compound CCNS(O)(=O)=O SIVVHUQWDOGLJN-UHFFFAOYSA-N 0.000 claims description 8
GQPIVVPQPRWBML-UHFFFAOYSA-N 4-methylpiperazine-1-sulfonic acid Chemical compound CN1CCN(S(O)(=O)=O)CC1 GQPIVVPQPRWBML-UHFFFAOYSA-N 0.000 claims description 7
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 7
WJMKFCHQPIKSSJ-UHFFFAOYSA-N 2-cyclohexyl-4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-3h-pyran-6-one Chemical compound C1C(O)=CC(=O)OC1(C1CCCCC1)CCC1=CC=C(O)C=C1 WJMKFCHQPIKSSJ-UHFFFAOYSA-N 0.000 claims description 6
AWBXBDFUKMIEMI-UHFFFAOYSA-N 4-hydroxy-2,2-bis[2-(3-hydroxyphenyl)ethyl]-3h-pyran-6-one Chemical compound C1C(O)=CC(=O)OC1(CCC=1C=C(O)C=CC=1)CCC1=CC=CC(O)=C1 AWBXBDFUKMIEMI-UHFFFAOYSA-N 0.000 claims description 6
NHOJHOYHWFTKFR-UHFFFAOYSA-N 4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-2-propan-2-yl-3h-pyran-6-one Chemical compound C=1C=C(O)C=CC=1CCC1(C(C)C)CC(O)=CC(=O)O1 NHOJHOYHWFTKFR-UHFFFAOYSA-N 0.000 claims description 6
NNHAQDVPZCLPNC-UHFFFAOYSA-N [4-[(2-tert-butyl-5-methylphenyl)methyl]phenyl]-hydroxy-oxo-sulfanylidene-lambda6-sulfane Chemical compound CC1=CC(=C(C=C1)C(C)(C)C)CC2=CC=C(C=C2)S(=O)(=S)O NNHAQDVPZCLPNC-UHFFFAOYSA-N 0.000 claims description 6
KSZCAGWHZCZJLZ-UHFFFAOYSA-N 1-methylimidazole-4-sulfonic acid Chemical compound CN1C=NC(S(O)(=O)=O)=C1 KSZCAGWHZCZJLZ-UHFFFAOYSA-N 0.000 claims description 5
HLRFVMVKUQFLTB-UHFFFAOYSA-N 2-[4-[2-[tert-butyl(dimethyl)silyl]oxyethoxy]phenyl]-4-hydroxy-2-(2-phenylethyl)-3h-pyran-6-one Chemical compound C1=CC(OCCO[Si](C)(C)C(C)(C)C)=CC=C1C1(CCC=2C=CC=CC=2)OC(=O)C=C(O)C1 HLRFVMVKUQFLTB-UHFFFAOYSA-N 0.000 claims description 5
GSIBFSUOSIOSAD-UHFFFAOYSA-N 2-butyl-4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-3h-pyran-6-one Chemical compound C=1C=C(O)C=CC=1CCC1(CCCC)CC(O)=CC(=O)O1 GSIBFSUOSIOSAD-UHFFFAOYSA-N 0.000 claims description 5
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
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 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
YADMGBDIWAVRBX-KRWDZBQOSA-N (3s)-3-hydroxy-3,5-diphenylpentanoic acid Chemical compound C([C@](O)(CC(=O)O)C=1C=CC=CC=1)CC1=CC=CC=C1 YADMGBDIWAVRBX-KRWDZBQOSA-N 0.000 claims description 4
FSSVIHHOKXDQMD-AWEZNQCLSA-N (3s)-3-hydroxy-3-[2-(4-hydroxyphenyl)ethyl]-4-methylpentanoic acid Chemical compound OC(=O)C[C@](O)(C(C)C)CCC1=CC=C(O)C=C1 FSSVIHHOKXDQMD-AWEZNQCLSA-N 0.000 claims description 4
HEFBKQNLHSGUFX-UHFFFAOYSA-N 1-[4-(2-hydroxyethoxy)phenyl]-3-phenylpropan-1-one Chemical compound C1=CC(OCCO)=CC=C1C(=O)CCC1=CC=CC=C1 HEFBKQNLHSGUFX-UHFFFAOYSA-N 0.000 claims description 4
ZRQVXDOJFANAPG-UHFFFAOYSA-N 2-cyclopentyl-4-hydroxy-2-[2-(3-phenylmethoxyphenyl)ethyl]-3h-pyran-6-one Chemical compound C1C(O)=CC(=O)OC1(C1CCCC1)CCC1=CC=CC(OCC=2C=CC=CC=2)=C1 ZRQVXDOJFANAPG-UHFFFAOYSA-N 0.000 claims description 4
STRJNZMKVUCZKT-UHFFFAOYSA-N 3-hydroxy-4-methyl-3-[2-(4-phenylmethoxyphenyl)ethyl]pentanoic acid Chemical compound C1=CC(CCC(O)(C(C)C)CC(O)=O)=CC=C1OCC1=CC=CC=C1 STRJNZMKVUCZKT-UHFFFAOYSA-N 0.000 claims description 4
UBSZJMGZEDDEAG-UHFFFAOYSA-N 4-hydroxy-2,2-bis[2-(4-hydroxy-3-methoxyphenyl)ethyl]-3h-pyran-6-one Chemical compound C1=C(O)C(OC)=CC(CCC2(CCC=3C=C(OC)C(O)=CC=3)OC(=O)C=C(O)C2)=C1 UBSZJMGZEDDEAG-UHFFFAOYSA-N 0.000 claims description 4
NCYILABWRPWKRP-UHFFFAOYSA-N 4-hydroxy-2-[2-(3-hydroxyphenyl)ethyl]-2-phenyl-3h-pyran-6-one Chemical compound C1C(O)=CC(=O)OC1(C=1C=CC=CC=1)CCC1=CC=CC(O)=C1 NCYILABWRPWKRP-UHFFFAOYSA-N 0.000 claims description 4
CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 4
VCISBAYASDURDY-FQEVSTJZSA-N methyl (5s)-5-hydroxy-3-oxo-5,7-diphenylheptanoate Chemical compound C([C@](O)(CC(=O)CC(=O)OC)C=1C=CC=CC=1)CC1=CC=CC=C1 VCISBAYASDURDY-FQEVSTJZSA-N 0.000 claims description 4
COWMGULBFGXHDP-UHFFFAOYSA-N methyl 3-hydroxy-4-methyl-3-[2-(4-phenylmethoxyphenyl)ethyl]pentanoate Chemical compound C1=CC(CCC(O)(CC(=O)OC)C(C)C)=CC=C1OCC1=CC=CC=C1 COWMGULBFGXHDP-UHFFFAOYSA-N 0.000 claims description 4
JBDYOOIKCQMYKF-UHFFFAOYSA-N tert-butyl 3-hydroxy-4-methyl-3-[2-(4-phenylmethoxyphenyl)ethyl]pentanoate Chemical compound C1=CC(CCC(O)(C(C)C)CC(=O)OC(C)(C)C)=CC=C1OCC1=CC=CC=C1 JBDYOOIKCQMYKF-UHFFFAOYSA-N 0.000 claims description 4
UFRCBUVLZQZWPP-MHZLTWQESA-N (2s)-5-(4-amino-2-tert-butyl-5-methylphenyl)sulfanyl-4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-2-propan-2-yl-3h-pyran-6-one Chemical compound C([C@]1(C(C)C)OC(=O)C(SC=2C(=CC(N)=C(C)C=2)C(C)(C)C)=C(O)C1)CC1=CC=C(O)C=C1 UFRCBUVLZQZWPP-MHZLTWQESA-N 0.000 claims description 3
ABQNHLNVRKLJGM-NMXAJACMSA-N (6S)-3-[2-tert-butyl-4-(hydroxymethyl)-5-methylphenyl]sulfanyl-6-[2-(4-hydroxyphenyl)ethyl]-6-propan-2-yloxane-2,4-dione Chemical compound C([C@]1(C(C)C)OC(=O)C(SC=2C(=CC(CO)=C(C)C=2)C(C)(C)C)C(=O)C1)CC1=CC=C(O)C=C1 ABQNHLNVRKLJGM-NMXAJACMSA-N 0.000 claims description 3
OBMCQQOLMRPQLY-UHFFFAOYSA-N 1,5-bis(3-phenylmethoxyphenyl)pentan-3-one Chemical compound C=1C=CC(OCC=2C=CC=CC=2)=CC=1CCC(=O)CCC(C=1)=CC=CC=1OCC1=CC=CC=C1 OBMCQQOLMRPQLY-UHFFFAOYSA-N 0.000 claims description 3
OMPGDQLBQOFCDF-UHFFFAOYSA-N 1,5-bis(4-phenylmethoxyphenyl)pentan-3-one Chemical compound C=1C=C(OCC=2C=CC=CC=2)C=CC=1CCC(=O)CCC(C=C1)=CC=C1OCC1=CC=CC=C1 OMPGDQLBQOFCDF-UHFFFAOYSA-N 0.000 claims description 3
BHWYSWYRTKETRK-UHFFFAOYSA-N 1-(4-hydroxyphenyl)-3-phenylpropan-1-one Chemical compound C1=CC(O)=CC=C1C(=O)CCC1=CC=CC=C1 BHWYSWYRTKETRK-UHFFFAOYSA-N 0.000 claims description 3
XINRYZXNTIPUGK-UHFFFAOYSA-N 1-[4-[2-[tert-butyl(dimethyl)silyl]oxyethoxy]phenyl]-3-phenylpropan-1-one Chemical compound C1=CC(OCCO[Si](C)(C)C(C)(C)C)=CC=C1C(=O)CCC1=CC=CC=C1 XINRYZXNTIPUGK-UHFFFAOYSA-N 0.000 claims description 3
FLZGYJSCXGYVQS-UHFFFAOYSA-N 1-cyclohexyl-3-(4-phenylmethoxyphenyl)propan-1-one Chemical compound C1CCCCC1C(=O)CCC(C=C1)=CC=C1OCC1=CC=CC=C1 FLZGYJSCXGYVQS-UHFFFAOYSA-N 0.000 claims description 3
OJFBWPKNFXGTOF-UHFFFAOYSA-N 2-[5-tert-butyl-2-methyl-4-(4-methylphenyl)sulfonylsulfanylphenoxy]acetic acid Chemical compound C1=CC(C)=CC=C1S(=O)(=O)SC1=CC(C)=C(OCC(O)=O)C=C1C(C)(C)C OJFBWPKNFXGTOF-UHFFFAOYSA-N 0.000 claims description 3
GCSCDVSACXBHOQ-UHFFFAOYSA-N 3-(3-hydroxyphenyl)-1-phenylpropan-1-one Chemical compound OC1=CC=CC(CCC(=O)C=2C=CC=CC=2)=C1 GCSCDVSACXBHOQ-UHFFFAOYSA-N 0.000 claims description 3
WYRIUKIUHKMEJX-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-1-phenylpropan-1-one Chemical compound C1=CC(O)=CC=C1CCC(=O)C1=CC=CC=C1 WYRIUKIUHKMEJX-UHFFFAOYSA-N 0.000 claims description 3
ZGNXLSZANVXEFY-UHFFFAOYSA-N 3-[3-[tert-butyl(dimethyl)silyl]oxyphenyl]-1-phenylpropan-1-one Chemical compound CC(C)(C)[Si](C)(C)OC1=CC=CC(CCC(=O)C=2C=CC=CC=2)=C1 ZGNXLSZANVXEFY-UHFFFAOYSA-N 0.000 claims description 3
CGFCIUTUFYUGHF-UHFFFAOYSA-N 3-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-1-phenylpropan-1-one Chemical compound C1=CC(O[Si](C)(C)C(C)(C)C)=CC=C1CCC(=O)C1=CC=CC=C1 CGFCIUTUFYUGHF-UHFFFAOYSA-N 0.000 claims description 3
SQSGHPOITYJTOQ-UHFFFAOYSA-N 4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-2-phenyl-3h-pyran-6-one Chemical compound C1C(O)=CC(=O)OC1(C=1C=CC=CC=1)CCC1=CC=C(O)C=C1 SQSGHPOITYJTOQ-UHFFFAOYSA-N 0.000 claims description 3
COEHMUNBPYEOSH-UHFFFAOYSA-N 5-(2-tert-butyl-4-hydroxy-5-methylphenyl)sulfanyl-2-cyclohexyl-4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-3h-pyran-6-one Chemical compound C1=C(O)C(C)=CC(SC=2C(OC(CCC=3C=CC(O)=CC=3)(CC=2O)C2CCCCC2)=O)=C1C(C)(C)C COEHMUNBPYEOSH-UHFFFAOYSA-N 0.000 claims description 3
JNOXWMVFARQNBU-UHFFFAOYSA-N 5-(2-tert-butyl-5-methylphenyl)sulfanyl-4-hydroxy-2-(2-phenylethyl)-2-[4-(2-piperazin-1-ylethoxy)phenyl]-3h-pyran-6-one Chemical compound CC1=CC=C(C(C)(C)C)C(SC=2C(OC(CCC=3C=CC=CC=3)(CC=2O)C=2C=CC(OCCN3CCNCC3)=CC=2)=O)=C1 JNOXWMVFARQNBU-UHFFFAOYSA-N 0.000 claims description 3
MCXJXZSEPHDGRS-UHFFFAOYSA-N 5-(2-tert-butyl-5-methylphenyl)sulfanyl-4-hydroxy-2-[4-(2-morpholin-4-ylethoxy)phenyl]-2-(2-phenylethyl)-3h-pyran-6-one Chemical compound CC1=CC=C(C(C)(C)C)C(SC=2C(OC(CCC=3C=CC=CC=3)(CC=2O)C=2C=CC(OCCN3CCOCC3)=CC=2)=O)=C1 MCXJXZSEPHDGRS-UHFFFAOYSA-N 0.000 claims description 3
SCCFOTYHMGKGJE-UHFFFAOYSA-N 5-(4-amino-2-tert-butyl-5-methylphenyl)sulfanyl-4-hydroxy-2,2-bis[2-(4-hydroxyphenyl)ethyl]-3h-pyran-6-one Chemical compound C1=C(N)C(C)=CC(SC=2C(OC(CCC=3C=CC(O)=CC=3)(CCC=3C=CC(O)=CC=3)CC=2O)=O)=C1C(C)(C)C SCCFOTYHMGKGJE-UHFFFAOYSA-N 0.000 claims description 3
XXTLJXMBWLYHNE-UHFFFAOYSA-N 5-(4-amino-2-tert-butyl-5-methylphenyl)sulfanyl-4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-2-methyl-3h-pyran-6-one Chemical compound C1=C(N)C(C)=CC(SC=2C(OC(C)(CCC=3C=CC(O)=CC=3)CC=2O)=O)=C1C(C)(C)C XXTLJXMBWLYHNE-UHFFFAOYSA-N 0.000 claims description 3
XPVMQANCNLMJFG-UHFFFAOYSA-N 5-[2-tert-butyl-4-(2-hydroxyethoxy)-5-methylphenyl]sulfanyl-4-hydroxy-2,2-bis[2-(4-hydroxyphenyl)ethyl]-3h-pyran-6-one Chemical compound C1=C(OCCO)C(C)=CC(SC=2C(OC(CCC=3C=CC(O)=CC=3)(CCC=3C=CC(O)=CC=3)CC=2O)=O)=C1C(C)(C)C XPVMQANCNLMJFG-UHFFFAOYSA-N 0.000 claims description 3
ZYVPQMFWSOQLEI-UHFFFAOYSA-N 5-[2-tert-butyl-4-(2-hydroxyethoxy)-5-methylphenyl]sulfanyl-4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-2-propan-2-yl-3h-pyran-6-one Chemical compound C1C(O)=C(SC=2C(=CC(OCCO)=C(C)C=2)C(C)(C)C)C(=O)OC1(C(C)C)CCC1=CC=C(O)C=C1 ZYVPQMFWSOQLEI-UHFFFAOYSA-N 0.000 claims description 3
JIAONJDPKLYQEB-UHFFFAOYSA-N 5-[2-tert-butyl-4-(hydroxymethyl)-5-methylphenyl]sulfanyl-2-cyclohexyl-4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-3h-pyran-6-one Chemical compound C1=C(CO)C(C)=CC(SC=2C(OC(CCC=3C=CC(O)=CC=3)(CC=2O)C2CCCCC2)=O)=C1C(C)(C)C JIAONJDPKLYQEB-UHFFFAOYSA-N 0.000 claims description 3
BDSSADARKUSVCY-UHFFFAOYSA-N 5-[2-tert-butyl-4-(hydroxymethyl)-5-methylphenyl]sulfanyl-4-hydroxy-2,2-bis[2-(4-hydroxyphenyl)ethyl]-3h-pyran-6-one Chemical compound C1=C(CO)C(C)=CC(SC=2C(OC(CCC=3C=CC(O)=CC=3)(CCC=3C=CC(O)=CC=3)CC=2O)=O)=C1C(C)(C)C BDSSADARKUSVCY-UHFFFAOYSA-N 0.000 claims description 3
IREQXHFFMVBBOH-UHFFFAOYSA-N 5-[2-tert-butyl-4-(hydroxymethyl)-5-methylphenyl]sulfanyl-4-hydroxy-2-[2-(3-hydroxyphenyl)ethyl]-2-phenyl-3h-pyran-6-one Chemical compound C1=C(CO)C(C)=CC(SC=2C(OC(CCC=3C=C(O)C=CC=3)(CC=2O)C=2C=CC=CC=2)=O)=C1C(C)(C)C IREQXHFFMVBBOH-UHFFFAOYSA-N 0.000 claims description 3
IVAQVNGJHLSQPY-UHFFFAOYSA-N 5-[2-tert-butyl-4-(hydroxymethyl)-5-methylphenyl]sulfanyl-4-hydroxy-2-phenyl-2-(2-phenylethyl)-3h-pyran-6-one Chemical compound C1=C(CO)C(C)=CC(SC=2C(OC(CCC=3C=CC=CC=3)(CC=2O)C=2C=CC=CC=2)=O)=C1C(C)(C)C IVAQVNGJHLSQPY-UHFFFAOYSA-N 0.000 claims description 3
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
QBLGZRQGQWLXHB-UHFFFAOYSA-N ethyl 2-[5-tert-butyl-4-[[4-hydroxy-2,2-bis[2-(4-hydroxyphenyl)ethyl]-6-oxo-3h-pyran-5-yl]sulfanyl]-2-methylphenoxy]acetate Chemical compound C1=C(C)C(OCC(=O)OCC)=CC(C(C)(C)C)=C1SC(C(O1)=O)=C(O)CC1(CCC=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 QBLGZRQGQWLXHB-UHFFFAOYSA-N 0.000 claims description 3
COKJTJVPSZTLEI-UHFFFAOYSA-N n-[4-(3-oxo-3-phenylpropyl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CCC(=O)C1=CC=CC=C1 COKJTJVPSZTLEI-UHFFFAOYSA-N 0.000 claims description 3
YYJYCQZCIDDWFJ-UHFFFAOYSA-N n-[4-[2-(4-hydroxy-6-oxo-2-phenyl-3h-pyran-2-yl)ethyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CCC1(C=2C=CC=CC=2)OC(=O)C=C(O)C1 YYJYCQZCIDDWFJ-UHFFFAOYSA-N 0.000 claims description 3
LHNJRBKDYMHDNR-UHFFFAOYSA-N n-[5-tert-butyl-4-[[4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-2-methyl-6-oxo-3h-pyran-5-yl]sulfanyl]-2-methylphenyl]-4-cyanobenzenesulfonamide Chemical compound CC(C)(C)C=1C=C(NS(=O)(=O)C=2C=CC(=CC=2)C#N)C(C)=CC=1SC(C(O1)=O)=C(O)CC1(C)CCC1=CC=C(O)C=C1 LHNJRBKDYMHDNR-UHFFFAOYSA-N 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
238000006467 substitution reaction Methods 0.000 claims description 3
125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
ITHRCOJJTOPXNO-UHFFFAOYSA-N tert-butyl 4-[2-[2-[4-hydroxy-6-oxo-2-(2-phenylethyl)-3h-pyran-2-yl]phenoxy]ethyl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1CCOC1=CC=CC=C1C1(CCC=2C=CC=CC=2)OC(=O)C=C(O)C1 ITHRCOJJTOPXNO-UHFFFAOYSA-N 0.000 claims description 3
NHOJHOYHWFTKFR-INIZCTEOSA-N (2s)-4-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]-2-propan-2-yl-3h-pyran-6-one Chemical compound C=1C=C(O)C=CC=1CC[C@@]1(C(C)C)CC(O)=CC(=O)O1 NHOJHOYHWFTKFR-INIZCTEOSA-N 0.000 claims description 2
OSXKEOWGCIAZRA-UHFFFAOYSA-N 1,5-bis(3-methoxy-4-phenylmethoxyphenyl)pentan-3-one Chemical compound C=1C=C(OCC=2C=CC=CC=2)C(OC)=CC=1CCC(=O)CCC(C=C1OC)=CC=C1OCC1=CC=CC=C1 OSXKEOWGCIAZRA-UHFFFAOYSA-N 0.000 claims description 2
LTPCZCRKBKIPHB-UHFFFAOYSA-N 1,5-bis(4-aminophenyl)pentan-3-one Chemical compound C1=CC(N)=CC=C1CCC(=O)CCC1=CC=C(N)C=C1 LTPCZCRKBKIPHB-UHFFFAOYSA-N 0.000 claims description 2
AJCNHMDQNSVCPY-UHFFFAOYSA-N 1,5-bis(4-nitrophenyl)pentan-3-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1CCC(=O)CCC1=CC=C([N+]([O-])=O)C=C1 AJCNHMDQNSVCPY-UHFFFAOYSA-N 0.000 claims description 2
SIUMPVVNSDRWHT-UHFFFAOYSA-N 4-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]butan-2-one Chemical compound CC(=O)CCC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1 SIUMPVVNSDRWHT-UHFFFAOYSA-N 0.000 claims description 2
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TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical class OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000007885 tablet disintegrant Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
KKHCZMKCCRUFLI-UHFFFAOYSA-N tert-butyl 3-cyclopentyl-3-hydroxy-5-(3-phenylmethoxyphenyl)pentanoate Chemical compound C1CCCC1C(O)(CC(=O)OC(C)(C)C)CCC(C=1)=CC=CC=1OCC1=CC=CC=C1 KKHCZMKCCRUFLI-UHFFFAOYSA-N 0.000 description 1
OGLHKDGHBSVBDF-UHFFFAOYSA-N tert-butyl 4-[2-[4-[5-(2-tert-butyl-5-methylphenyl)sulfanyl-4-hydroxy-6-oxo-2-(2-phenylethyl)-3h-pyran-2-yl]phenoxy]ethyl]piperazine-1-carboxylate Chemical compound CC1=CC=C(C(C)(C)C)C(SC=2C(OC(CCC=3C=CC=CC=3)(CC=2O)C=2C=CC(OCCN3CCN(CC3)C(=O)OC(C)(C)C)=CC=2)=O)=C1 OGLHKDGHBSVBDF-UHFFFAOYSA-N 0.000 description 1
MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
125000005309 thioalkoxy group Chemical group 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 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
DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 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
- 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
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
- 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
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
- C07C233/33—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/04—Thiosulfonates
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/48—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/52—Unsaturated compounds containing hydroxy or O-metal groups a hydroxy or O-metal group being bound to a carbon atom of a six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
- 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

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Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
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Life Sciences & Earth Sciences (AREA)
Virology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Tropical Medicine & Parasitology (AREA)
Communicable Diseases (AREA)
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General Chemical & Material Sciences (AREA)
AIDS & HIV (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Molecular Biology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pyrane Compounds (AREA)

HR08/883,743A 1996-11-01 1997-10-27 Dihydropyrones with improved antiviral activity HRP970571A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US2990696P	1996-11-01	1996-11-01
US08/883,743 US5834506A (en)	1996-11-01	1997-06-27	Dihydropyrones with improved antiviral activity

Publications (1)

Publication Number	Publication Date
HRP970571A2 true HRP970571A2 (en)	1998-08-31

Family

ID=26705464

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR08/883,743A HRP970571A2 (en)	1996-11-01	1997-10-27	Dihydropyrones with improved antiviral activity

Country Status (18)

Country	Link
US (2)	US5834506A (no)
EP (1)	EP0935597A2 (no)
JP (1)	JP2001504102A (no)
KR (4)	KR100496367B1 (no)
AU (1)	AU733700B2 (no)
BR (1)	BR9714588A (no)
CA (1)	CA2263429A1 (no)
CO (1)	CO4910146A1 (no)
HR (1)	HRP970571A2 (no)
IL (1)	IL128517A (no)
MX (1)	MXPA99001777A (no)
MY (1)	MY118131A (no)
NO (1)	NO992103L (no)
NZ (2)	NZ334701A (no)
PE (1)	PE13799A1 (no)
PL (1)	PL332904A1 (no)
TW (1)	TW536536B (no)
WO (1)	WO1998019997A2 (no)

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WO1999014210A1 (en) *	1997-09-15	1999-03-25	Warner-Lambert Company	Process for the preparation of substituted 5,6-dihydro-2h-pyran-2-ones
US6380400B1 (en) *	1998-09-11	2002-04-30	Victor Fedij	Methods of making dihydropyrone HIV protease inhibitors
CA2339275A1 (en)	1998-09-11	2000-03-23	Warner-Lambert Company	5,6-dihydro-4-hydroxy-2-pyranones as hiv aspartyl protease inhibitors
US6054623A (en) *	1998-12-18	2000-04-25	Alliedsignal Inc.	Hydroxythiol grignard reaction synthesis
US6512006B1 (en)	1999-12-09	2003-01-28	Warner-Lambert Company	HIV protease inhibitors
WO2002020509A2 (de) *	2000-09-06	2002-03-14	Bayer Aktiengesellschaft	Arzneimittel gegen virale erkrankungen
US7141681B2 (en)	2001-02-22	2006-11-28	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Continuous process for preparing dihydropyrones
DE10108471C1 (de)	2001-02-22	2002-11-21	Boehringer Ingelheim Pharma	Kontinuierliches Verfahren zur Herstellung von 5,6-Dihydro-4-hydroxy-2-pyronen
WO2002072549A1 (en) *	2001-03-12	2002-09-19	Millennium Pharmaceuticals, Inc.	Functionalized heterocycles as modulators of chemokine receptor function and methods of use therefor
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
DE10257761A1 (de)	2002-12-10	2004-06-24	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Verfahren zur Herstellung optisch aktiver Dihydropyrone
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
AU2005273619B2 (en) *	2004-08-18	2009-05-28	Pfizer Inc.	Inhibitors of hepatitis C virus RNA-dependent RNA polymerase, and compositions and treatments using the same
RU2493147C2 (ru)	2007-12-20	2013-09-20	Фарма Мар, С.А.	Противоопухолевые соединения
US12083099B2 (en)	2020-10-28	2024-09-10	Accencio LLC	Methods of treating symptoms of coronavirus infection with viral protease inhibitors

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JPS57167296A (en) *	1981-04-09	1982-10-15	Ricoh Co Ltd	Heat-sensitive recording material
FI962021A7 (fi) *	1993-11-19	1996-07-12	Parke Davis & Co	5,6-dihydropyronijohdannaiset proteaasi-inhibiittoreina ja antiviraali sina aineina
RU2140917C1 (ru) *	1993-11-19	1999-11-10	Парк, Дэвис энд Компани	Производные 5,6-дигидропирона и фармацевтическая композиция на их основе
IL129871A (en) *	1994-05-06	2003-11-23	Pharmacia & Upjohn Inc	Process for preparing 4-phenyl-substituted octanoyl-oxazolidin-2-one intermediates that are useful for preparing pyran-2-ones useful for treating retroviral infections

1997
- 1997-06-27 US US08/883,743 patent/US5834506A/en not_active Expired - Fee Related
- 1997-10-24 TW TW086115796A patent/TW536536B/zh not_active IP Right Cessation
- 1997-10-27 HR HR08/883,743A patent/HRP970571A2/hr not_active Application Discontinuation
- 1997-10-31 KR KR10-2004-7017282A patent/KR100496367B1/ko not_active Expired - Fee Related
- 1997-10-31 NZ NZ334701A patent/NZ334701A/xx unknown
- 1997-10-31 PE PE1997000976A patent/PE13799A1/es not_active Application Discontinuation
- 1997-10-31 KR KR10-2004-7017280A patent/KR100496365B1/ko not_active Expired - Fee Related
- 1997-10-31 KR KR10-2004-7017281A patent/KR100496366B1/ko not_active Expired - Fee Related
- 1997-10-31 BR BR9714588-2A patent/BR9714588A/pt not_active Application Discontinuation
- 1997-10-31 EP EP97913943A patent/EP0935597A2/en not_active Withdrawn
- 1997-10-31 AU AU51001/98A patent/AU733700B2/en not_active Ceased
- 1997-10-31 CA CA002263429A patent/CA2263429A1/en not_active Abandoned
- 1997-10-31 PL PL97332904A patent/PL332904A1/xx unknown
- 1997-10-31 WO PCT/US1997/019853 patent/WO1998019997A2/en not_active Ceased
- 1997-10-31 NZ NZ507184A patent/NZ507184A/en unknown
- 1997-10-31 MX MXPA99001777A patent/MXPA99001777A/es unknown
- 1997-10-31 KR KR1019990703824A patent/KR20000052951A/ko not_active Abandoned
- 1997-10-31 JP JP52160798A patent/JP2001504102A/ja not_active Abandoned
- 1997-10-31 IL IL12851797A patent/IL128517A/xx not_active IP Right Cessation
- 1997-10-31 CO CO97064202A patent/CO4910146A1/es unknown
- 1997-11-01 MY MYPI97005184A patent/MY118131A/en unknown
1998
- 1998-07-28 US US09/124,190 patent/US6046355A/en not_active Expired - Fee Related
1999
- 1999-04-30 NO NO992103A patent/NO992103L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
IL128517A (en)	2003-07-31
IL128517A0 (en)	2000-01-31
CA2263429A1 (en)	1998-05-14
JP2001504102A (ja)	2001-03-27
MY118131A (en)	2004-09-30
CO4910146A1 (es)	2000-04-24
BR9714588A (pt)	2000-05-30
WO1998019997A3 (en)	1998-08-27
KR20040104645A (ko)	2004-12-10
NZ507184A (en)	2002-02-01
AU733700B2 (en)	2001-05-24
KR20040104644A (ko)	2004-12-10
KR20040104646A (ko)	2004-12-10
KR100496367B1 (ko)	2005-06-22
NO992103D0 (no)	1999-04-30
EP0935597A2 (en)	1999-08-18
US5834506A (en)	1998-11-10
KR20000052951A (ko)	2000-08-25
PL332904A1 (en)	1999-10-25
KR100496366B1 (ko)	2005-06-21
TW536536B (en)	2003-06-11
KR100496365B1 (ko)	2005-06-21
NZ334701A (en)	2001-01-26
MXPA99001777A (es)	2003-08-10
NO992103L (no)	1999-04-30
WO1998019997A2 (en)	1998-05-14
PE13799A1 (es)	1999-02-26
AU5100198A (en)	1998-05-29
US6046355A (en)	2000-04-04

Legal Events

Date	Code	Title
1998-08-31	A1OB	Publication of a patent application
1999-02-26	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
2002-10-21	ODBC	Application rejected

Publication	Publication Date	Title
HRP970571A2 (en)	1998-08-31	Dihydropyrones with improved antiviral activity
AU688417B2 (en)	1998-03-12	Catecholamine surrogates usful as beta3 agonists
US5308865A (en)	1994-05-03	2-cyano-3-hydroxy-enamides
US20070293495A1 (en)	2007-12-20	Beta-amyloid protein production/secretion inhibitors
HU200594B (en)	1990-07-28	Process for producing arylhydroxamates
AU4645997A (en)	1998-04-17	Beta-sulfonyl hydroxamic acids as matrix metalloproteinases inhibitors
KR20010032042A (ko)	2001-04-16	엠엠피와 티엔에프 억제 활성을 갖는 히드록삼산 및카르복실산 유도체
MXPA04012857A (es)	2005-02-24	Derivados de acido fenilalcanoico y de acido feniloxialcanoico como activadores de receptores activados del proliferador de peroxisoma humano (hppar).
PT96379B (pt)	1998-06-30	Processo de preparacao de ciclopropil-n-hidroxi-ureias,-carboxamidas e n-acil-n-hidroxiaminas substituidas e de composicoes farmaceuticas
US20100261772A1 (en)	2010-10-14	Cycloalkylidene Compounds As Selective Estrogen Receptor Modulators
IE904522A1 (en)	1991-06-19	Pharmacologically Active Amide Carboxylate Derivatives
EP1089963A1 (en)	2001-04-11	Hydroxamic acid derivatives as inhibitors of the production of human cd23 and of the tnf release
EP0494621B1 (en)	1995-08-02	Substituted alkenoic acid and its derivatives
FR2707989A1 (fr)	1995-01-27	Nouveaux dérivés de benzylamines silylées, leurs sels, leurs procédés de fabrication et les compositions pharmaceutiques les renfermant.
EP0811612B1 (en)	1999-03-03	Process for preparing dithiocarbonimide derivatives
EP1680410A1 (en)	2006-07-19	Thiazole-2-carboxamide derivatives for use as hppar agonists in the treatment of i.a. dyslipidemia
HK1127592A1 (en)	2009-10-02	(r)-arylkylamino derivatives and pharmaceutical compositions containing them
JP2006045108A (ja)	2006-02-16	３−（ｎ−アシルアミノ）−３−（４−テトラヒドロピラニル）プロペン酸エステル及びその製法
JPS6216940B2 (no)	1987-04-15
JPH0623153B2 (ja)	1994-03-30	インダン誘導体の製法及びその合成中間体
ZA200300121B (en)	2004-01-21	Cyclopentyl-substituted glutaramide derivatives as inhibitors of neutral endopeptidase.