NO319914B1 - Pyran-2-oner og 5,6-dihydropyran-2-oner, anvendelse derav til fremstilling av medikamenter som kan anvendes for behandling av HIV og inhibering av andre retrovirus, farmasoytiske preparater som omfatter forbindelsene, fremgangsmate for fremstilling av et pyran-2-on, samt forbindelse som er et mellomprodukt i fremgangsmaten. - Google Patents
Pyran-2-oner og 5,6-dihydropyran-2-oner, anvendelse derav til fremstilling av medikamenter som kan anvendes for behandling av HIV og inhibering av andre retrovirus, farmasoytiske preparater som omfatter forbindelsene, fremgangsmate for fremstilling av et pyran-2-on, samt forbindelse som er et mellomprodukt i fremgangsmaten. Download PDFInfo
- Publication number
- NO319914B1 NO319914B1 NO19951899A NO951899A NO319914B1 NO 319914 B1 NO319914 B1 NO 319914B1 NO 19951899 A NO19951899 A NO 19951899A NO 951899 A NO951899 A NO 951899A NO 319914 B1 NO319914 B1 NO 319914B1
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy
- pyran
- cyclopropylphenylmethyl
- ethyl
- cyclopropyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 318
- 238000002360 preparation method Methods 0.000 title claims description 171
- 238000000034 method Methods 0.000 title claims description 81
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical class O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 title claims description 69
- 241001430294 unidentified retrovirus Species 0.000 title claims description 26
- 239000003814 drug Substances 0.000 title claims description 15
- QBDAFARLDLCWAT-UHFFFAOYSA-N 2,3-dihydropyran-6-one Chemical class O=C1OCCC=C1 QBDAFARLDLCWAT-UHFFFAOYSA-N 0.000 title description 15
- 230000005764 inhibitory process Effects 0.000 title description 8
- 230000008569 process Effects 0.000 title description 6
- 239000008194 pharmaceutical composition Substances 0.000 title 1
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims abstract description 14
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims abstract description 14
- 206010020112 Hirsutism Diseases 0.000 claims abstract description 8
- 208000002874 Acne Vulgaris Diseases 0.000 claims abstract description 7
- 206010039792 Seborrhoea Diseases 0.000 claims abstract description 7
- 206010000496 acne Diseases 0.000 claims abstract description 7
- 208000008742 seborrheic dermatitis Diseases 0.000 claims abstract description 7
- 201000004384 Alopecia Diseases 0.000 claims abstract description 6
- 206010060862 Prostate cancer Diseases 0.000 claims abstract description 6
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 5
- 231100000360 alopecia Toxicity 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 98
- -1 hydroxy- Chemical class 0.000 claims description 86
- 125000003118 aryl group Chemical group 0.000 claims description 84
- 230000002829 reductive effect Effects 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 64
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 61
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 58
- 229910052736 halogen Inorganic materials 0.000 claims description 57
- 150000002367 halogens Chemical class 0.000 claims description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 51
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 42
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 40
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
- 125000005843 halogen group Chemical group 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 34
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 28
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 27
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 22
- 125000001041 indolyl group Chemical group 0.000 claims description 20
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 20
- HALPINAQGOXQAN-UHFFFAOYSA-N 4-hydroxy-6-(1-phenylbutan-2-yl)-3-(1-phenylpropyl)pyran-2-one Chemical compound C=1C(O)=C(C(CC)C=2C=CC=CC=2)C(=O)OC=1C(CC)CC1=CC=CC=C1 HALPINAQGOXQAN-UHFFFAOYSA-N 0.000 claims description 19
- 125000004076 pyridyl group Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 15
- 210000002307 prostate Anatomy 0.000 claims description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 13
- 125000001624 naphthyl group Chemical group 0.000 claims description 13
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- OAXPPAUXOZJCFF-UHFFFAOYSA-N 4-hydroxy-6-(2-phenylethyl)-3-(1-phenylpropyl)pyran-2-one Chemical compound OC=1C=C(CCC=2C=CC=CC=2)OC(=O)C=1C(CC)C1=CC=CC=C1 OAXPPAUXOZJCFF-UHFFFAOYSA-N 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 11
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 10
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 10
- 125000003386 piperidinyl group Chemical group 0.000 claims description 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
- CCXHMPZXKYIXPU-UHFFFAOYSA-N undec-3-en-2-one Chemical compound CCCCCCCC=CC(C)=O CCXHMPZXKYIXPU-UHFFFAOYSA-N 0.000 claims description 10
- 125000000539 amino acid group Chemical group 0.000 claims description 9
- 125000002757 morpholinyl group Chemical group 0.000 claims description 9
- 230000002265 prevention Effects 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims description 8
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 8
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 8
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
- 125000005493 quinolyl group Chemical group 0.000 claims description 8
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 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 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- NIWRYPYYEGRGKQ-UHFFFAOYSA-N 3-[cyclopropyl(phenyl)methyl]-4-hydroxy-6-(1-phenylbutan-2-yl)pyran-2-one Chemical compound C=1C(O)=C(C(C2CC2)C=2C=CC=CC=2)C(=O)OC=1C(CC)CC1=CC=CC=C1 NIWRYPYYEGRGKQ-UHFFFAOYSA-N 0.000 claims description 7
- JMDSLWXUUIGCIE-UHFFFAOYSA-N 4-hydroxy-2-(2-phenylethyl)-5-(1-phenylprop-2-enyl)-2-propyl-3h-pyran-6-one Chemical compound C1C(O)=C(C(C=C)C=2C=CC=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 JMDSLWXUUIGCIE-UHFFFAOYSA-N 0.000 claims description 7
- LUVPIDXNOFOISJ-UHFFFAOYSA-N 6-(1,3-dicyclopropylpropan-2-yl)-3-(1,3-diphenylpropan-2-yl)-4-hydroxypyran-2-one Chemical compound OC=1C=C(C(CC2CC2)CC2CC2)OC(=O)C=1C(CC=1C=CC=CC=1)CC1=CC=CC=C1 LUVPIDXNOFOISJ-UHFFFAOYSA-N 0.000 claims description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- RLUOCJYZFIFUPW-VHEBQXMUSA-N (e)-n-[3-[cyclopropyl-[4-hydroxy-2-oxo-6-(1-phenylbutan-2-yl)pyran-3-yl]methyl]phenyl]-2-phenylethenesulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)\C=C\C=3C=CC=CC=3)C=CC=2)C(=O)OC=1C(CC)CC1=CC=CC=C1 RLUOCJYZFIFUPW-VHEBQXMUSA-N 0.000 claims description 6
- XEUKVFCEEWWMDX-UHFFFAOYSA-N 3-[cyclopropyl(phenyl)methyl]-4-hydroxy-6-[1-(oxan-3-yl)butan-2-yl]pyran-2-one Chemical compound C=1C(O)=C(C(C2CC2)C=2C=CC=CC=2)C(=O)OC=1C(CC)CC1CCCOC1 XEUKVFCEEWWMDX-UHFFFAOYSA-N 0.000 claims description 6
- LEGVWCMROWYYGB-UHFFFAOYSA-N 3-[cyclopropyl(phenyl)methyl]-4-hydroxy-6-[3-methyl-1-(oxan-3-yl)butan-2-yl]pyran-2-one Chemical compound C=1C(O)=C(C(C2CC2)C=2C=CC=CC=2)C(=O)OC=1C(C(C)C)CC1CCCOC1 LEGVWCMROWYYGB-UHFFFAOYSA-N 0.000 claims description 6
- UDRHGFHNMBOPMA-UHFFFAOYSA-N 3-[cyclopropyl(phenyl)methyl]-6-(3-cyclopropylpropyl)-4-hydroxypyran-2-one Chemical compound O1C(=O)C(C(C2CC2)C=2C=CC=CC=2)=C(O)C=C1CCCC1CC1 UDRHGFHNMBOPMA-UHFFFAOYSA-N 0.000 claims description 6
- IDAKOCJEIMLSJC-UHFFFAOYSA-N 4-bromo-n-[3-[cyclopropyl-[4-hydroxy-2-oxo-6-(1-phenylbutan-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(Br)=CC=3)C=CC=2)C(=O)OC=1C(CC)CC1=CC=CC=C1 IDAKOCJEIMLSJC-UHFFFAOYSA-N 0.000 claims description 6
- OCXOYYFOGHBUKE-UHFFFAOYSA-N 4-cyano-n-[3-[cyclopropyl-[4-hydroxy-2-oxo-6-(1-phenylbutan-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#N)C=CC=2)C(=O)OC=1C(CC)CC1=CC=CC=C1 OCXOYYFOGHBUKE-UHFFFAOYSA-N 0.000 claims description 6
- LUVPETPCXKTVRE-UHFFFAOYSA-N 4-hydroxy-2-(2-phenylethyl)-5-(1-phenylpropyl)-2-propyl-3h-pyran-6-one Chemical compound C1C(O)=C(C(CC)C=2C=CC=CC=2)C(=O)OC1(CCC)CCC1=CC=CC=C1 LUVPETPCXKTVRE-UHFFFAOYSA-N 0.000 claims description 6
- JASUGPXTCSFKPU-UHFFFAOYSA-N 4-hydroxy-6-[1-(oxan-3-yl)butan-2-yl]-3-(1-phenylpropyl)pyran-2-one Chemical compound C=1C(O)=C(C(CC)C=2C=CC=CC=2)C(=O)OC=1C(CC)CC1CCCOC1 JASUGPXTCSFKPU-UHFFFAOYSA-N 0.000 claims description 6
- KPNLBNFNTOBJPP-UHFFFAOYSA-N 4-hydroxy-6-phenyl-3-(1-phenylpropyl)pyran-2-one Chemical compound OC=1C=C(C=2C=CC=CC=2)OC(=O)C=1C(CC)C1=CC=CC=C1 KPNLBNFNTOBJPP-UHFFFAOYSA-N 0.000 claims description 6
- IXMQTFMSJCZFGJ-UHFFFAOYSA-N 6-[2-(4-bromophenyl)ethyl]-4-hydroxy-3-(1-phenylpropyl)pyran-2-one Chemical compound OC=1C=C(CCC=2C=CC(Br)=CC=2)OC(=O)C=1C(CC)C1=CC=CC=C1 IXMQTFMSJCZFGJ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 claims description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- VEXRXPAIHVICKW-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-2-oxo-6-(1-phenylbutan-2-yl)pyran-3-yl]methyl]phenyl]-4-methoxybenzenesulfonamide Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NS(=O)(=O)C=3C=CC(OC)=CC=3)C=CC=2)C(=O)OC=1C(CC)CC1=CC=CC=C1 VEXRXPAIHVICKW-UHFFFAOYSA-N 0.000 claims description 6
- KPHRDRFCGGZQJY-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-2-oxo-6-(1-phenylbutan-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(CC)CC1=CC=CC=C1 KPHRDRFCGGZQJY-UHFFFAOYSA-N 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 5
- SZMFLLFXCUWETL-UHFFFAOYSA-N 2-benzyl-4-hydroxy-2-phenyl-5-(1-phenylprop-2-enyl)-3h-pyran-6-one Chemical compound O=C1OC(CC=2C=CC=CC=2)(C=2C=CC=CC=2)CC(O)=C1C(C=C)C1=CC=CC=C1 SZMFLLFXCUWETL-UHFFFAOYSA-N 0.000 claims description 5
- VMYGWUZDAVHAED-UHFFFAOYSA-N 2-benzyl-5-(1,3-diphenylprop-2-enyl)-4-hydroxy-2-propyl-3h-pyran-6-one Chemical compound C1C(O)=C(C(C=CC=2C=CC=CC=2)C=2C=CC=CC=2)C(=O)OC1(CCC)CC1=CC=CC=C1 VMYGWUZDAVHAED-UHFFFAOYSA-N 0.000 claims description 5
- NHQOGYUDKNEOAJ-UHFFFAOYSA-N 3-[cyclopropyl(phenyl)methyl]-4-hydroxy-6-(1-thiophen-3-ylpentan-3-yl)pyran-2-one Chemical compound C=1C(O)=C(C(C2CC2)C=2C=CC=CC=2)C(=O)OC=1C(CC)CCC=1C=CSC=1 NHQOGYUDKNEOAJ-UHFFFAOYSA-N 0.000 claims description 5
- BGJWCRRDALNYLX-UHFFFAOYSA-N 3-[cyclopropyl(phenyl)methyl]-4-hydroxy-6-(6,6,6-trifluorohexan-3-yl)pyran-2-one Chemical compound O=C1OC(C(CCC(F)(F)F)CC)=CC(O)=C1C(C=1C=CC=CC=1)C1CC1 BGJWCRRDALNYLX-UHFFFAOYSA-N 0.000 claims description 5
- ZIQFCITVGPLHGU-UHFFFAOYSA-N 3-[cyclopropyl(phenyl)methyl]-4-hydroxy-6-[1-(oxolan-2-yl)butan-2-yl]pyran-2-one Chemical compound C=1C(O)=C(C(C2CC2)C=2C=CC=CC=2)C(=O)OC=1C(CC)CC1CCCO1 ZIQFCITVGPLHGU-UHFFFAOYSA-N 0.000 claims description 5
- ZEMOQTORBGRWIA-UHFFFAOYSA-N 3-[cyclopropyl(phenyl)methyl]-4-hydroxy-6-[1-(oxolan-3-yl)butan-2-yl]pyran-2-one Chemical compound C=1C(O)=C(C(C2CC2)C=2C=CC=CC=2)C(=O)OC=1C(CC)CC1CCOC1 ZEMOQTORBGRWIA-UHFFFAOYSA-N 0.000 claims description 5
- NLPUJWLJYWMFBP-UHFFFAOYSA-N 3-[cyclopropyl(phenyl)methyl]-4-hydroxy-6-[4-(2-methoxyethoxy)-1-phenylbutan-2-yl]pyran-2-one Chemical compound C=1C(O)=C(C(C2CC2)C=2C=CC=CC=2)C(=O)OC=1C(CCOCCOC)CC1=CC=CC=C1 NLPUJWLJYWMFBP-UHFFFAOYSA-N 0.000 claims description 5
- MTZINKANLRZRLH-UHFFFAOYSA-N 3-[cyclopropyl(phenyl)methyl]-4-hydroxy-6-methylpyran-2-one Chemical compound O=C1OC(C)=CC(O)=C1C(C=1C=CC=CC=1)C1CC1 MTZINKANLRZRLH-UHFFFAOYSA-N 0.000 claims description 5
- NPUSYATYOAJXRJ-UHFFFAOYSA-N 3-[cyclopropyl(phenyl)methyl]-6-[1-(furan-2-yl)butan-2-yl]-4-hydroxypyran-2-one Chemical compound C=1C(O)=C(C(C2CC2)C=2C=CC=CC=2)C(=O)OC=1C(CC)CC1=CC=CO1 NPUSYATYOAJXRJ-UHFFFAOYSA-N 0.000 claims description 5
- SEUIMKBYBKTVTL-UHFFFAOYSA-N 4-chloro-n-[3-[cyclopropyl-[4-hydroxy-2-oxo-6-(1-phenylbutan-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(Cl)=CC=3)C=CC=2)C(=O)OC=1C(CC)CC1=CC=CC=C1 SEUIMKBYBKTVTL-UHFFFAOYSA-N 0.000 claims description 5
- FZZBUBJWEHXAKW-UHFFFAOYSA-N 4-hydroxy-2-(2-methylpropyl)-2-(2-phenylethyl)-5-(1-phenylprop-2-enyl)-3h-pyran-6-one Chemical compound C1C(O)=C(C(C=C)C=2C=CC=CC=2)C(=O)OC1(CC(C)C)CCC1=CC=CC=C1 FZZBUBJWEHXAKW-UHFFFAOYSA-N 0.000 claims description 5
- YANGOUQCLQYXJU-UHFFFAOYSA-N 4-hydroxy-2-(2-methylpropyl)-2-(2-phenylethyl)-5-(1-phenylpropyl)-3h-pyran-6-one Chemical compound C=1C=CC=CC=1C(CC)C(C(O1)=O)=C(O)CC1(CC(C)C)CCC1=CC=CC=C1 YANGOUQCLQYXJU-UHFFFAOYSA-N 0.000 claims description 5
- ZEEIVCACYPMCAW-UHFFFAOYSA-N 4-hydroxy-3-(1-phenylpropyl)-6-(3-phenylpropyl)pyran-2-one Chemical compound OC=1C=C(CCCC=2C=CC=CC=2)OC(=O)C=1C(CC)C1=CC=CC=C1 ZEEIVCACYPMCAW-UHFFFAOYSA-N 0.000 claims description 5
- PIKLWMHNSAYFLQ-UHFFFAOYSA-N 4-hydroxy-3-(1-phenylpropyl)-6-propylpyran-2-one Chemical compound O=C1OC(CCC)=CC(O)=C1C(CC)C1=CC=CC=C1 PIKLWMHNSAYFLQ-UHFFFAOYSA-N 0.000 claims description 5
- RCIDYDLLIALKGH-UHFFFAOYSA-N 4-hydroxy-3-(6-phenyloctan-3-yl)pyran-2-one Chemical compound C=1C=CC=CC=1C(CC)CCC(CC)C1=C(O)C=COC1=O RCIDYDLLIALKGH-UHFFFAOYSA-N 0.000 claims description 5
- IIVCYYLSRRSAII-UHFFFAOYSA-N 4-hydroxy-6-methyl-3-(3-phenylprop-2-enyl)pyran-2-one Chemical compound O=C1OC(C)=CC(O)=C1CC=CC1=CC=CC=C1 IIVCYYLSRRSAII-UHFFFAOYSA-N 0.000 claims description 5
- HXYLUFZYAYSNEH-UHFFFAOYSA-N 5-benzhydryl-4-hydroxy-2-(3-phenylpropyl)-2-propyl-3h-pyran-6-one Chemical compound C1C(O)=C(C(C=2C=CC=CC=2)C=2C=CC=CC=2)C(=O)OC1(CCC)CCCC1=CC=CC=C1 HXYLUFZYAYSNEH-UHFFFAOYSA-N 0.000 claims description 5
- NRSHLQALBMFWBM-UHFFFAOYSA-N 6-(1-chloropentan-3-yl)-3-[cyclopropyl(phenyl)methyl]-4-hydroxypyran-2-one Chemical compound O=C1OC(C(CCCl)CC)=CC(O)=C1C(C=1C=CC=CC=1)C1CC1 NRSHLQALBMFWBM-UHFFFAOYSA-N 0.000 claims description 5
- KXFCDPRZVYWLAM-UHFFFAOYSA-N 6-(6-chlorohexan-3-yl)-3-[cyclopropyl(phenyl)methyl]-4-hydroxypyran-2-one Chemical compound O=C1OC(C(CCCCl)CC)=CC(O)=C1C(C=1C=CC=CC=1)C1CC1 KXFCDPRZVYWLAM-UHFFFAOYSA-N 0.000 claims description 5
- BKJTZOSEHTYZNC-UHFFFAOYSA-N 6-[2-(2-fluorophenyl)ethyl]-4-hydroxy-3-(1-phenylpropyl)pyran-2-one Chemical compound OC=1C=C(CCC=2C(=CC=CC=2)F)OC(=O)C=1C(CC)C1=CC=CC=C1 BKJTZOSEHTYZNC-UHFFFAOYSA-N 0.000 claims description 5
- JCQNOBVRXMXPMP-UHFFFAOYSA-N 6-benzyl-4-hydroxy-3-(1-phenylpropyl)pyran-2-one Chemical compound OC=1C=C(CC=2C=CC=CC=2)OC(=O)C=1C(CC)C1=CC=CC=C1 JCQNOBVRXMXPMP-UHFFFAOYSA-N 0.000 claims description 5
- CVNLTKAKWGPYEY-UHFFFAOYSA-N 6-but-3-enyl-4-hydroxy-3-(1-phenylpropyl)pyran-2-one Chemical compound OC=1C=C(CCC=C)OC(=O)C=1C(CC)C1=CC=CC=C1 CVNLTKAKWGPYEY-UHFFFAOYSA-N 0.000 claims description 5
- 125000006374 C2-C10 alkenyl group Chemical group 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
- 239000003937 drug carrier Substances 0.000 claims description 5
- GTGPHAUFYVHIIY-UHFFFAOYSA-N n-[3-[cyclopropyl-[4-hydroxy-2-oxo-6-(1-phenylbutan-2-yl)pyran-3-yl]methyl]phenyl]propane-1-sulfonamide Chemical compound CCCS(=O)(=O)NC1=CC=CC(C(C2CC2)C=2C(OC(=CC=2O)C(CC)CC=2C=CC=CC=2)=O)=C1 GTGPHAUFYVHIIY-UHFFFAOYSA-N 0.000 claims description 5
- DCTZEPZZPJUAND-OZGZLMSGSA-N (4s)-4-amino-5-[3-[cyclopropyl-[4-hydroxy-2-oxo-6-(1-phenylbutan-2-yl)pyran-3-yl]methyl]anilino]-5-oxopentanoic acid Chemical compound C=1C(O)=C(C(C2CC2)C=2C=C(NC(=O)[C@@H](N)CCC(O)=O)C=CC=2)C(=O)OC=1C(CC)CC1=CC=CC=C1 DCTZEPZZPJUAND-OZGZLMSGSA-N 0.000 claims description 4
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- HEJUEWNMWDCQRG-UHFFFAOYSA-N tert-butyl 3-benzyl-4-phenylbutanoate Chemical compound C=1C=CC=CC=1CC(CC(=O)OC(C)(C)C)CC1=CC=CC=C1 HEJUEWNMWDCQRG-UHFFFAOYSA-N 0.000 description 1
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- IIHPVYJPDKJYOU-UHFFFAOYSA-N triphenylcarbethoxymethylenephosphorane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OCC)C1=CC=CC=C1 IIHPVYJPDKJYOU-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
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- 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
- C07D405/06—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 only aliphatic carbon atoms
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- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
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- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/26—Androgens
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/34—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D309/36—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms
- C07D309/38—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with oxygen atoms directly attached to ring carbon atoms one oxygen atom in position 2 or 4, e.g. pyrones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/96—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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- C07D413/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Dermatology (AREA)
- AIDS & HIV (AREA)
- Tropical Medicine & Parasitology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Plant Substances (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US97534392A | 1992-11-13 | 1992-11-13 | |
US9087693A | 1993-07-13 | 1993-07-13 | |
US13064193A | 1993-10-01 | 1993-10-01 | |
PCT/US1993/010645 WO1994011361A1 (en) | 1992-11-13 | 1993-11-09 | Pyran-2-ones and 5,6-dihydropyran-2-ones useful for treating hiv and other retroviruses |
Publications (3)
Publication Number | Publication Date |
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NO951899D0 NO951899D0 (no) | 1995-05-12 |
NO951899L NO951899L (no) | 1995-07-12 |
NO319914B1 true NO319914B1 (no) | 2005-10-03 |
Family
ID=27376682
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19951899A NO319914B1 (no) | 1992-11-13 | 1995-05-12 | Pyran-2-oner og 5,6-dihydropyran-2-oner, anvendelse derav til fremstilling av medikamenter som kan anvendes for behandling av HIV og inhibering av andre retrovirus, farmasoytiske preparater som omfatter forbindelsene, fremgangsmate for fremstilling av et pyran-2-on, samt forbindelse som er et mellomprodukt i fremgangsmaten. |
Country Status (26)
Country | Link |
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EP (2) | EP1203770B1 (ru) |
JP (1) | JP3583127B2 (ru) |
KR (1) | KR100314975B1 (ru) |
CN (1) | CN1040321C (ru) |
AT (2) | ATE290531T1 (ru) |
AU (1) | AU687368B2 (ru) |
BR (1) | BR9307451A (ru) |
CA (1) | CA2145661C (ru) |
CZ (1) | CZ291853B6 (ru) |
DE (2) | DE69333771T2 (ru) |
DK (2) | DK0668860T3 (ru) |
ES (2) | ES2182837T3 (ru) |
FI (1) | FI120399B (ru) |
GE (1) | GEP20094660B (ru) |
HU (1) | HU228126B1 (ru) |
IL (1) | IL107556A (ru) |
LV (1) | LV13088B (ru) |
MY (1) | MY119031A (ru) |
NO (1) | NO319914B1 (ru) |
NZ (1) | NZ258013A (ru) |
PL (1) | PL178653B1 (ru) |
PT (2) | PT668860E (ru) |
RU (1) | RU2134691C1 (ru) |
SK (1) | SK285001B6 (ru) |
WO (1) | WO1994011361A1 (ru) |
ZA (1) | ZA938019B (ru) |
Families Citing this family (39)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TW354294B (en) * | 1993-09-17 | 1999-03-11 | Upjohn Co | Substituted tetronic acids useful for treating HIV and other retroviruses |
US5840751A (en) * | 1993-11-19 | 1998-11-24 | Warner-Lambert Company | 5,6-dihydropyrone derivatives as protease inhibitors and antiviral agents |
EP0729466A1 (en) * | 1993-11-19 | 1996-09-04 | PARKE, DAVIS & COMPANY | Pyrone derivatives as protease inhibitors and antiviral agents |
JP3684426B2 (ja) * | 1993-11-19 | 2005-08-17 | パーク・デイビス・アンド・カンパニー | 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 |
JP3698435B2 (ja) * | 1993-11-19 | 2005-09-21 | パーク・デイビス・アンド・カンパニー | 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 |
US6005103A (en) * | 1993-11-19 | 1999-12-21 | Warner-Lambert Company | Pyrone derivatives as protease inhibitors and antiviral agents |
DE69432056T2 (de) * | 1993-11-19 | 2003-10-09 | Parke, Davis & Company | Pyron derivate als protease inhibitoren und antivirusmitteln |
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 |
AU5417696A (en) * | 1995-03-20 | 1996-10-08 | Upjohn Company, The | Substituted tetronic acids useful for treating hiv and other retroviruses |
WO1998000173A2 (en) * | 1996-07-03 | 1998-01-08 | Pharmacia & Upjohn Company | Targeted drug delivery using sulfonamide derivatives |
EP1015441B1 (en) * | 1997-09-11 | 2004-05-12 | PHARMACIA & UPJOHN COMPANY | Process to produce 4-hydroxy-2-oxo-pyrane derivatives useful as protease inhibitors |
DE69917237T2 (de) | 1998-03-12 | 2005-05-04 | Teijin Ltd. | Benzofurylpyron-derivate |
EP1281399A3 (en) * | 2001-08-01 | 2004-02-11 | Warner-Lambert Company | Dual inhibitors of wax ester and cholesteryl ester synthesis for inhibiting sebum production |
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 |
CN102030645A (zh) | 2003-10-24 | 2011-04-27 | 隆萨股份公司 | 6,6,6-三卤-3,5-二氧代己酸酯的制备方法 |
EP2032551B9 (en) * | 2006-06-16 | 2012-02-29 | Pharma Mar, S.A. | Antitumoral dihydropyran-2-one compounds |
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FR1276654A (fr) * | 1958-10-01 | 1961-11-24 | Nouveaux dérivés de l'hydroxy-4-alpha-2-pyrone | |
FR1276645A (fr) * | 1959-12-28 | 1961-11-17 | Wild Heerbrugg Ag | Objectif de microscope |
AU4074789A (en) * | 1988-03-01 | 1989-09-22 | Upjohn Company, The | Coumarins to inhibit reverse transcriptase in humans |
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