CH646966A5 - Die cholesterinbiosynthese hemmende verbindungen, ihre herstellung und verwendung. - Google Patents
Die cholesterinbiosynthese hemmende verbindungen, ihre herstellung und verwendung. Download PDFInfo
- Publication number
- CH646966A5 CH646966A5 CH215381A CH215381A CH646966A5 CH 646966 A5 CH646966 A5 CH 646966A5 CH 215381 A CH215381 A CH 215381A CH 215381 A CH215381 A CH 215381A CH 646966 A5 CH646966 A5 CH 646966A5
- Authority
- CH
- Switzerland
- Prior art keywords
- group
- hydrogen atom
- butyryl
- carbon atoms
- straight
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 49
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 title description 16
- 230000015572 biosynthetic process Effects 0.000 title description 7
- 238000004519 manufacturing process Methods 0.000 title description 7
- 230000002401 inhibitory effect Effects 0.000 title description 5
- HVYWMOMLDIMFJA-UHFFFAOYSA-N 3-cholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 HVYWMOMLDIMFJA-UHFFFAOYSA-N 0.000 title 1
- AJLFOPYRIVGYMJ-INTXDZFKSA-N mevastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=CCC[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 AJLFOPYRIVGYMJ-INTXDZFKSA-N 0.000 claims description 127
- -1 methylenedioxy groups Chemical group 0.000 claims description 104
- LXZBFUBRYYVRQJ-AXHZAXLDSA-M sodium;(3r,5r)-7-[(1s,2s,6r,8s,8ar)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoate Chemical compound [Na+].C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC([O-])=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C=C21 LXZBFUBRYYVRQJ-AXHZAXLDSA-M 0.000 claims description 96
- WWSNTLOVYSRDEL-DZSDEGEFSA-N compactin diol lactone Chemical class C([C@@H]1[C@H]2[C@@H](O)CCC=C2C=C[C@@H]1C)C[C@@H]1C[C@@H](O)CC(=O)O1 WWSNTLOVYSRDEL-DZSDEGEFSA-N 0.000 claims description 89
- WWSNTLOVYSRDEL-UHFFFAOYSA-N desmethylmonacolin J Natural products CC1C=CC2=CCCC(O)C2C1CCC1CC(O)CC(=O)O1 WWSNTLOVYSRDEL-UHFFFAOYSA-N 0.000 claims description 86
- 125000002252 acyl group Chemical group 0.000 claims description 31
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
- 244000005700 microbiome Species 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 14
- 239000001963 growth medium Substances 0.000 claims description 13
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 10
- 238000005917 acylation reaction Methods 0.000 claims description 9
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 9
- 230000010933 acylation Effects 0.000 claims description 8
- 150000008065 acid anhydrides Chemical class 0.000 claims description 7
- 150000004820 halides Chemical class 0.000 claims description 7
- 241000031003 Monascus ruber Species 0.000 claims description 6
- 150000007530 organic bases Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 241000228347 Monascus <ascomycete fungus> Species 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 150000005690 diesters Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 239000013543 active substance Substances 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 52
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 238000000862 absorption spectrum Methods 0.000 description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 39
- 238000000921 elemental analysis Methods 0.000 description 38
- 239000007788 liquid Substances 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 7
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000007942 carboxylates Chemical class 0.000 description 6
- 235000012000 cholesterol Nutrition 0.000 description 6
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 6
- REEZZSHJLXOIHL-UHFFFAOYSA-N octanoyl chloride Chemical compound CCCCCCCC(Cl)=O REEZZSHJLXOIHL-UHFFFAOYSA-N 0.000 description 6
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- CDMVQQAHEQVSMF-AULARHRYSA-N 3-[(3s,5s,8r,9s,10r,13r,14s,17r)-3,14-dihydroxy-10-(hydroxymethyl)-13-methyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2h-furan-5-one Chemical compound C1([C@H]2CC[C@]3(O)[C@H]4[C@@H]([C@]5(CC[C@H](O)C[C@@H]5CC4)CO)CC[C@@]32C)=CC(=O)OC1 CDMVQQAHEQVSMF-AULARHRYSA-N 0.000 description 4
- ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012264 purified product Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- BVHMITOWPMCRLY-HZJYTTRNSA-N (6z,9z)-18-chlorooctadeca-6,9-diene Chemical compound CCCCC\C=C/C\C=C/CCCCCCCCCl BVHMITOWPMCRLY-HZJYTTRNSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000001888 Peptone Substances 0.000 description 3
- 108010080698 Peptones Proteins 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- ARBOVOVUTSQWSS-UHFFFAOYSA-N hexadecanoyl chloride Chemical compound CCCCCCCCCCCCCCCC(Cl)=O ARBOVOVUTSQWSS-UHFFFAOYSA-N 0.000 description 3
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 3
- 229940049918 linoleate Drugs 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 3
- 235000019319 peptone Nutrition 0.000 description 3
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 description 2
- FODBVCSYJKNBLO-UHFFFAOYSA-M 2,3-dimethoxybenzoate Chemical compound COC1=CC=CC(C([O-])=O)=C1OC FODBVCSYJKNBLO-UHFFFAOYSA-M 0.000 description 2
- JATAKEDDMQNPOQ-UHFFFAOYSA-M 2,4,6-trimethoxybenzoate Chemical compound COC1=CC(OC)=C(C([O-])=O)C(OC)=C1 JATAKEDDMQNPOQ-UHFFFAOYSA-M 0.000 description 2
- GPVDHNVGGIAOQT-UHFFFAOYSA-N 2,4-dimethoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C(OC)=C1 GPVDHNVGGIAOQT-UHFFFAOYSA-N 0.000 description 2
- NYJBTJMNTNCTCP-UHFFFAOYSA-M 2,5-dimethoxybenzoate Chemical compound COC1=CC=C(OC)C(C([O-])=O)=C1 NYJBTJMNTNCTCP-UHFFFAOYSA-M 0.000 description 2
- MBIZFBDREVRUHY-UHFFFAOYSA-N 2,6-Dimethoxybenzoic acid Chemical compound COC1=CC=CC(OC)=C1C(O)=O MBIZFBDREVRUHY-UHFFFAOYSA-N 0.000 description 2
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 2
- OBETXYAYXDNJHR-UHFFFAOYSA-N 2-Ethylhexanoic acid Chemical compound CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 2
- LZPNXAULYJPXEH-UHFFFAOYSA-N 2-Propenoic acid, 3-(3-methoxyphenyl)- Chemical compound COC1=CC=CC(C=CC(O)=O)=C1 LZPNXAULYJPXEH-UHFFFAOYSA-N 0.000 description 2
- XRXMNWGCKISMOH-UHFFFAOYSA-N 2-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1Br XRXMNWGCKISMOH-UHFFFAOYSA-N 0.000 description 2
- UABHETFCVNRGNL-UHFFFAOYSA-N 2-butoxybenzoic acid Chemical compound CCCCOC1=CC=CC=C1C(O)=O UABHETFCVNRGNL-UHFFFAOYSA-N 0.000 description 2
- IKCLCGXPQILATA-UHFFFAOYSA-M 2-chlorobenzoate Chemical compound [O-]C(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-M 0.000 description 2
- XDZMPRGFOOFSBL-UHFFFAOYSA-N 2-ethoxybenzoic acid Chemical compound CCOC1=CC=CC=C1C(O)=O XDZMPRGFOOFSBL-UHFFFAOYSA-N 0.000 description 2
- CGMMPMYKMDITEA-UHFFFAOYSA-N 2-ethylbenzoic acid Chemical compound CCC1=CC=CC=C1C(O)=O CGMMPMYKMDITEA-UHFFFAOYSA-N 0.000 description 2
- NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-M 2-furoate Chemical compound [O-]C(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-M 0.000 description 2
- DGMOBVGABMBZSB-UHFFFAOYSA-N 2-methylpropanoyl chloride Chemical compound CC(C)C(Cl)=O DGMOBVGABMBZSB-UHFFFAOYSA-N 0.000 description 2
- OXOWWPXTTOCKKU-UHFFFAOYSA-N 2-propoxybenzoic acid Chemical compound CCCOC1=CC=CC=C1C(O)=O OXOWWPXTTOCKKU-UHFFFAOYSA-N 0.000 description 2
- SJSOFNCYXJUNBT-UHFFFAOYSA-N 3,4,5-trimethoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=CC(OC)=C1OC SJSOFNCYXJUNBT-UHFFFAOYSA-N 0.000 description 2
- OMHDOOAFLCMRFX-UHFFFAOYSA-N 3-(2-bromophenyl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CC=C1Br OMHDOOAFLCMRFX-UHFFFAOYSA-N 0.000 description 2
- KJRRTHHNKJBVBO-UHFFFAOYSA-N 3-(2-chlorophenyl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CC=C1Cl KJRRTHHNKJBVBO-UHFFFAOYSA-N 0.000 description 2
- FEGVSPGUHMGGBO-UHFFFAOYSA-N 3-(2-methoxyphenyl)-2-propenoic acid Chemical compound COC1=CC=CC=C1C=CC(O)=O FEGVSPGUHMGGBO-UHFFFAOYSA-N 0.000 description 2
- RSWBWHPZXKLUEX-UHFFFAOYSA-N 3-(2-methylphenyl)prop-2-enoic acid Chemical compound CC1=CC=CC=C1C=CC(O)=O RSWBWHPZXKLUEX-UHFFFAOYSA-N 0.000 description 2
- YEMUSDCFQUBPAL-UHFFFAOYSA-N 3-(3-bromophenyl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CC(Br)=C1 YEMUSDCFQUBPAL-UHFFFAOYSA-N 0.000 description 2
- FFKGOJWPSXRALK-UHFFFAOYSA-N 3-(3-chlorophenyl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CC(Cl)=C1 FFKGOJWPSXRALK-UHFFFAOYSA-N 0.000 description 2
- JZINNAKNHHQBOS-UHFFFAOYSA-N 3-(3-methylphenyl)prop-2-enoic acid Chemical compound CC1=CC=CC(C=CC(O)=O)=C1 JZINNAKNHHQBOS-UHFFFAOYSA-N 0.000 description 2
- CPDDDTNAMBSPRN-UHFFFAOYSA-N 3-(4-bromophenyl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=C(Br)C=C1 CPDDDTNAMBSPRN-UHFFFAOYSA-N 0.000 description 2
- GXLIFJYFGMHYDY-UHFFFAOYSA-N 3-(4-chlorophenyl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=C(Cl)C=C1 GXLIFJYFGMHYDY-UHFFFAOYSA-N 0.000 description 2
- RURHILYUWQEGOS-UHFFFAOYSA-N 3-(4-methylphenyl)prop-2-enoic acid Chemical compound CC1=CC=C(C=CC(O)=O)C=C1 RURHILYUWQEGOS-UHFFFAOYSA-N 0.000 description 2
- VOIZNVUXCQLQHS-UHFFFAOYSA-N 3-bromobenzoic acid Chemical compound OC(=O)C1=CC=CC(Br)=C1 VOIZNVUXCQLQHS-UHFFFAOYSA-N 0.000 description 2
- DNGXQBZMSWQUKS-UHFFFAOYSA-N 3-butoxybenzoic acid Chemical compound CCCCOC1=CC=CC(C(O)=O)=C1 DNGXQBZMSWQUKS-UHFFFAOYSA-N 0.000 description 2
- LULAYUGMBFYYEX-UHFFFAOYSA-M 3-chlorobenzoate Chemical compound [O-]C(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-M 0.000 description 2
- DTFQMPQJMDEWKJ-UHFFFAOYSA-N 3-ethoxybenzoic acid Chemical compound CCOC1=CC=CC(C(O)=O)=C1 DTFQMPQJMDEWKJ-UHFFFAOYSA-N 0.000 description 2
- MXNBDFWNYRNIBH-UHFFFAOYSA-M 3-fluorobenzoate Chemical compound [O-]C(=O)C1=CC=CC(F)=C1 MXNBDFWNYRNIBH-UHFFFAOYSA-M 0.000 description 2
- IHCCAYCGZOLTEU-UHFFFAOYSA-M 3-furoate Chemical compound [O-]C(=O)C=1C=COC=1 IHCCAYCGZOLTEU-UHFFFAOYSA-M 0.000 description 2
- IJFXRHURBJZNAO-UHFFFAOYSA-N 3-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC(O)=C1 IJFXRHURBJZNAO-UHFFFAOYSA-N 0.000 description 2
- XHQZJYCNDZAGLW-UHFFFAOYSA-M 3-methoxybenzoate Chemical compound COC1=CC=CC(C([O-])=O)=C1 XHQZJYCNDZAGLW-UHFFFAOYSA-M 0.000 description 2
- IGIDLTISMCAULB-UHFFFAOYSA-N 3-methylvaleric acid Chemical compound CCC(C)CC(O)=O IGIDLTISMCAULB-UHFFFAOYSA-N 0.000 description 2
- XMIIGOLPHOKFCH-UHFFFAOYSA-M 3-phenylpropionate Chemical compound [O-]C(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-M 0.000 description 2
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- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 1
- 125000001402 nonanoyl group Chemical group O=C([*])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
- 235000015097 nutrients Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-M pentadecanoate Chemical compound CCCCCCCCCCCCCCC([O-])=O WQEPLUUGTLDZJY-UHFFFAOYSA-M 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000035479 physiological effects, processes and functions Effects 0.000 description 1
- VDVJGIYXDVPQLP-UHFFFAOYSA-M piperonylate Chemical compound [O-]C(=O)C1=CC=C2OCOC2=C1 VDVJGIYXDVPQLP-UHFFFAOYSA-M 0.000 description 1
- 229950010765 pivalate Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-M propynoate Chemical compound [O-]C(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-M 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])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])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
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- UIERETOOQGIECD-ONEGZZNKSA-N tiglic acid Chemical compound C\C=C(/C)C(O)=O UIERETOOQGIECD-ONEGZZNKSA-N 0.000 description 1
- 125000005607 tigloyl group Chemical group 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])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
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/02—Oxygen as only ring hetero atoms
- C12P17/06—Oxygen as only ring hetero atoms containing a six-membered hetero ring, e.g. fluorescein
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55041292A JPH0692381B2 (ja) | 1980-03-31 | 1980-03-31 | Ｍｂ−５３０ａ誘導体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH646966A5 true CH646966A5 (de) | 1984-12-28 |
Family
ID=12604367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH215381A CH646966A5 (de) | 1980-03-31 | 1981-03-30 | Die cholesterinbiosynthese hemmende verbindungen, ihre herstellung und verwendung. |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPH0692381B2 (ja) |
| AT (1) | ATA150781A (ja) |
| AU (1) | AU6893281A (ja) |
| BE (1) | BE888214A (ja) |
| CH (1) | CH646966A5 (ja) |
| DE (2) | DE3112566A1 (ja) |
| DK (3) | DK151273C (ja) |
| FI (1) | FI810991L (ja) |
| FR (1) | FR2479222A1 (ja) |
| GB (1) | GB2073193A (ja) |
| IE (1) | IE52367B1 (ja) |
| IT (1) | IT1144325B (ja) |
| MX (1) | MX9203567A (ja) |
| NL (1) | NL8101592A (ja) |
| SE (1) | SE461590B (ja) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4472426A (en) * | 1982-12-22 | 1984-09-18 | Merck & Co., Inc. | Antihypercholesterolemic compounds |
| DE3682557D1 (de) * | 1985-09-13 | 1992-01-02 | Sankyo Co | Hydroxy-ml-236b-derivate, deren herstellung und anwendung. |
| US4997848A (en) * | 1987-10-27 | 1991-03-05 | Sankyo Company, Limited | Octahydronaphthalene oxime derivatives for cholesterol synthesis inhibition |
| US5075327A (en) * | 1988-08-10 | 1991-12-24 | Hoffmann-La Roche Inc. | Antipsoriatic agents |
| US5021451A (en) * | 1988-11-14 | 1991-06-04 | Hoffman-La Roche Inc. | Method for inhibiting hyperproliferative diseases |
| US5200549A (en) * | 1988-11-14 | 1993-04-06 | Hoffman-La Roche Inc. | Antipsoriatic agents |
| US5073568A (en) * | 1988-11-14 | 1991-12-17 | Hoffmann-La Roche Inc. | Antipsoriatic agents |
| US5159104A (en) * | 1991-05-01 | 1992-10-27 | Merck & Co., Inc. | Process to simvastatin ester |
| FR2937537A1 (fr) * | 2008-10-29 | 2010-04-30 | Centre Nat Rech Scient | Nanoparticules de statine |
| KR101820099B1 (ko) | 2013-01-18 | 2018-01-18 | 에스프린팅솔루션 주식회사 | 저항 발열체, 이를 채용한 가열 부재, 및 정착 장치 |
| RU2020126177A (ru) | 2018-01-09 | 2022-02-10 | Лиганд Фармасьютикалз, Инк. | Ацетальные соединения и их терапевтическое применение |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5612114B2 (ja) * | 1974-06-07 | 1981-03-18 | ||
| JPS5925599B2 (ja) * | 1979-02-20 | 1984-06-19 | 三共株式会社 | 新生理活性物質モナコリンｋおよびその製造法 |
| US4231938A (en) * | 1979-06-15 | 1980-11-04 | Merck & Co., Inc. | Hypocholesteremic fermentation products and process of preparation |
| AU535944B2 (en) * | 1979-06-15 | 1984-04-12 | Merck & Co., Inc. | Hypocholestermic fermentation products from aspergillus |
| PT72394B (en) * | 1980-02-04 | 1982-09-06 | Merck & Co Inc | Process for preparing dihydro and tetrahydromevinoline hypocholesterolimics |
| US4282155A (en) * | 1980-02-04 | 1981-08-04 | Merck & Co., Inc. | Antihypercholesterolemic compounds |
| AU548996B2 (en) * | 1980-02-04 | 1986-01-09 | Merck & Co., Inc. | Tetrahydro-2h-pyran-2-one derivatives |
| ZA81703B (en) * | 1980-02-04 | 1982-09-29 | Merck & Co Inc | New antihypercholesterolemic compounds,intermediates and processes |
-
1980
- 1980-03-31 JP JP55041292A patent/JPH0692381B2/ja not_active Expired - Lifetime
-
1981
- 1981-03-27 IE IE698/81A patent/IE52367B1/en not_active IP Right Cessation
- 1981-03-30 DE DE19813112566 patent/DE3112566A1/de active Granted
- 1981-03-30 CH CH215381A patent/CH646966A5/de not_active IP Right Cessation
- 1981-03-30 IT IT67438/81A patent/IT1144325B/it active
- 1981-03-30 DE DE3153666A patent/DE3153666C2/de not_active Expired - Lifetime
- 1981-03-31 BE BE0/204328A patent/BE888214A/fr not_active IP Right Cessation
- 1981-03-31 AT AT0150781A patent/ATA150781A/de not_active IP Right Cessation
- 1981-03-31 FI FI810991A patent/FI810991L/fi not_active Application Discontinuation
- 1981-03-31 GB GB8110075A patent/GB2073193A/en not_active Withdrawn
- 1981-03-31 NL NL8101592A patent/NL8101592A/nl not_active Application Discontinuation
- 1981-03-31 DK DK145481A patent/DK151273C/da not_active IP Right Cessation
- 1981-03-31 FR FR8106403A patent/FR2479222A1/fr active Granted
- 1981-03-31 AU AU68932/81A patent/AU6893281A/en not_active Abandoned
- 1981-03-31 SE SE8102047A patent/SE461590B/sv not_active Application Discontinuation
-
1990
- 1990-02-07 DK DK032290A patent/DK32290A/da not_active Application Discontinuation
- 1990-02-07 DK DK032190A patent/DK167805B1/da not_active IP Right Cessation
-
1992
- 1992-06-26 MX MX9203567A patent/MX9203567A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU6893281A (en) | 1981-10-08 |
| SE8102047L (sv) | 1981-10-01 |
| DK145481A (da) | 1981-10-01 |
| DE3112566A1 (de) | 1982-03-11 |
| IT1144325B (it) | 1986-10-29 |
| BE888214A (fr) | 1981-09-30 |
| ATA150781A (de) | 1983-03-15 |
| DK32290D0 (da) | 1990-02-07 |
| DK32290A (da) | 1990-02-07 |
| DK167805B1 (da) | 1993-12-20 |
| FR2479222B1 (ja) | 1983-08-26 |
| MX9203567A (es) | 1992-09-01 |
| DK32190D0 (da) | 1990-02-07 |
| GB2073193A (en) | 1981-10-14 |
| JPS56138181A (en) | 1981-10-28 |
| FR2479222A1 (fr) | 1981-10-02 |
| DK32190A (da) | 1990-02-07 |
| SE461590B (sv) | 1990-03-05 |
| DK151273C (da) | 1988-07-04 |
| IT8167438A0 (it) | 1981-03-30 |
| IE810698L (en) | 1981-09-30 |
| DE3153666C2 (de) | 1993-11-11 |
| DK151273B (da) | 1987-11-16 |
| FI810991L (fi) | 1981-10-01 |
| JPH0692381B2 (ja) | 1994-11-16 |
| DE3112566C2 (ja) | 1990-04-05 |
| NL8101592A (nl) | 1981-10-16 |
| IE52367B1 (en) | 1987-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |