JPH0132811B2 - - Google Patents
Info
- Publication number
- JPH0132811B2 JPH0132811B2 JP55185143A JP18514380A JPH0132811B2 JP H0132811 B2 JPH0132811 B2 JP H0132811B2 JP 55185143 A JP55185143 A JP 55185143A JP 18514380 A JP18514380 A JP 18514380A JP H0132811 B2 JPH0132811 B2 JP H0132811B2
- Authority
- JP
- Japan
- Prior art keywords
- bis
- oxy
- phenylene
- carbon atoms
- dimethyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 238000000034 method Methods 0.000 claims abstract description 18
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 17
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000001301 oxygen Substances 0.000 claims abstract description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000011593 sulfur Substances 0.000 claims abstract description 10
- 150000003457 sulfones Chemical class 0.000 claims abstract description 7
- 150000003462 sulfoxides Chemical class 0.000 claims abstract description 6
- 239000000047 product Substances 0.000 claims description 41
- -1 methoxy, phenyl Chemical group 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- ZRYCZAWRXHAAPZ-UHFFFAOYSA-N alpha,alpha-dimethyl valeric acid Chemical compound CCCC(C)(C)C(O)=O ZRYCZAWRXHAAPZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 5
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 5
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 5
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- VHPUQUQWRUQIEH-UHFFFAOYSA-N methyl 5-[3-benzoyl-4-(5-methoxy-4,4-dimethyl-5-oxopentoxy)phenoxy]-2,2-dimethylpentanoate Chemical group COC(=O)C(C)(C)CCCOC1=CC=C(OCCCC(C)(C)C(=O)OC)C(C(=O)C=2C=CC=CC=2)=C1 VHPUQUQWRUQIEH-UHFFFAOYSA-N 0.000 claims description 3
- QOPRDXVVBBTZGN-UHFFFAOYSA-N methyl 5-[4-(5-methoxy-4,4-dimethyl-5-oxopentoxy)-3-propanoylphenoxy]-2,2-dimethylpentanoate Chemical group CCC(=O)C1=CC(OCCCC(C)(C)C(=O)OC)=CC=C1OCCCC(C)(C)C(=O)OC QOPRDXVVBBTZGN-UHFFFAOYSA-N 0.000 claims description 3
- BAYWIZSRWSTNAM-UHFFFAOYSA-N 4-[4-(3-carboxy-3-methylbutoxy)-3-chlorophenoxy]-2,2-dimethylbutanoic acid Chemical compound OC(=O)C(C)(C)CCOC1=CC=C(OCCC(C)(C)C(O)=O)C(Cl)=C1 BAYWIZSRWSTNAM-UHFFFAOYSA-N 0.000 claims description 2
- URLYJMPANKWBAJ-UHFFFAOYSA-N 5-[3-(benzenesulfinyl)-4-(4-carboxy-4-methylpentoxy)phenoxy]-2,2-dimethylpentanoic acid Chemical group OC(=O)C(C)(C)CCCOC1=CC=C(OCCCC(C)(C)C(O)=O)C(S(=O)C=2C=CC=CC=2)=C1 URLYJMPANKWBAJ-UHFFFAOYSA-N 0.000 claims description 2
- DTDFPDNLFHBONN-UHFFFAOYSA-N 5-[4-(4-carboxy-4-methylpentoxy)-2,5-dichlorophenoxy]-2,2-dimethylpentanoic acid Chemical group OC(=O)C(C)(C)CCCOC1=CC(Cl)=C(OCCCC(C)(C)C(O)=O)C=C1Cl DTDFPDNLFHBONN-UHFFFAOYSA-N 0.000 claims description 2
- QEXBXQJEDZRQAO-UHFFFAOYSA-N 5-[4-(4-carboxy-4-methylpentoxy)-3-(1-hydroxybutyl)phenoxy]-2,2-dimethylpentanoic acid Chemical group CCCC(O)C1=CC(OCCCC(C)(C)C(O)=O)=CC=C1OCCCC(C)(C)C(O)=O QEXBXQJEDZRQAO-UHFFFAOYSA-N 0.000 claims description 2
- SXPGSIDYGWNBKW-UHFFFAOYSA-N 5-[4-(4-carboxy-4-methylpentoxy)-3-(2-hydroxyethyl)phenoxy]-2,2-dimethylpentanoic acid Chemical group OC(=O)C(C)(C)CCCOC1=CC=C(OCCCC(C)(C)C(O)=O)C(CCO)=C1 SXPGSIDYGWNBKW-UHFFFAOYSA-N 0.000 claims description 2
- AYRSLTJAEIKDNI-UHFFFAOYSA-N 5-[4-(4-carboxy-4-methylpentoxy)-3-(trifluoromethyl)phenoxy]-2,2-dimethylpentanoic acid Chemical group OC(=O)C(C)(C)CCCOC1=CC=C(OCCCC(C)(C)C(O)=O)C(C(F)(F)F)=C1 AYRSLTJAEIKDNI-UHFFFAOYSA-N 0.000 claims description 2
- HLXIBHVZODFAKF-UHFFFAOYSA-N 5-[4-(4-carboxy-4-methylpentoxy)-3-chlorophenoxy]-2,2-dimethylpentanoic acid Chemical compound OC(=O)C(C)(C)CCCOC1=CC=C(OCCCC(C)(C)C(O)=O)C(Cl)=C1 HLXIBHVZODFAKF-UHFFFAOYSA-N 0.000 claims description 2
- CJNZDBIXYDLGBC-UHFFFAOYSA-N 5-[4-(4-carboxy-4-methylpentoxy)phenoxy]-2,2-dimethylpentanoic acid Chemical group OC(=O)C(C)(C)CCCOC1=CC=C(OCCCC(C)(C)C(O)=O)C=C1 CJNZDBIXYDLGBC-UHFFFAOYSA-N 0.000 claims description 2
- FEZZGHBMLLVGSQ-UHFFFAOYSA-N 6-[4-(5-carboxy-5-methylhexoxy)phenoxy]-2,2-dimethylhexanoic acid Chemical group OC(=O)C(C)(C)CCCCOC1=CC=C(OCCCCC(C)(C)C(O)=O)C=C1 FEZZGHBMLLVGSQ-UHFFFAOYSA-N 0.000 claims description 2
- BAFICOWLMLCEOZ-UHFFFAOYSA-N 6-[4-(6-hydroxy-5,5-dimethylhexoxy)phenoxy]-2,2-dimethylhexan-1-ol Chemical group OCC(C)(C)CCCCOC1=CC=C(OCCCCC(C)(C)CO)C=C1 BAFICOWLMLCEOZ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- AKZHICWBVJYIMV-UHFFFAOYSA-N methyl 5-[3-acetyl-4-(5-methoxy-4,4-dimethyl-5-oxopentoxy)phenoxy]-2,2-dimethylpentanoate Chemical group COC(=O)C(C)(C)CCCOC1=CC=C(OCCCC(C)(C)C(=O)OC)C(C(C)=O)=C1 AKZHICWBVJYIMV-UHFFFAOYSA-N 0.000 claims description 2
- RYBGVLSWXSTVGU-UHFFFAOYSA-N methyl 5-[3-fluoro-4-(5-methoxy-4,4-dimethyl-5-oxopentoxy)phenoxy]-2,2-dimethylpentanoate Chemical group COC(=O)C(C)(C)CCCOC1=CC=C(OCCCC(C)(C)C(=O)OC)C(F)=C1 RYBGVLSWXSTVGU-UHFFFAOYSA-N 0.000 claims description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical group O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- BKHAYKFEQUCJRD-UHFFFAOYSA-N 5-[3-benzyl-4-(4-carboxy-4-methylpentoxy)phenoxy]-2,2-dimethylpentanoic acid Chemical group OC(=O)C(C)(C)CCCOC1=CC=C(OCCCC(C)(C)C(O)=O)C(CC=2C=CC=CC=2)=C1 BKHAYKFEQUCJRD-UHFFFAOYSA-N 0.000 claims 1
- YCFUWKKOLSGRTL-UHFFFAOYSA-N methyl 5-[3-bromo-4-(5-methoxy-4,4-dimethyl-5-oxopentoxy)phenoxy]-2,2-dimethylpentanoate Chemical group COC(=O)C(C)(C)CCCOC1=CC=C(OCCCC(C)(C)C(=O)OC)C(Br)=C1 YCFUWKKOLSGRTL-UHFFFAOYSA-N 0.000 claims 1
- IPFAQBQEPAFDSA-UHFFFAOYSA-N methyl 5-[3-methoxy-4-(5-methoxy-4,4-dimethyl-5-oxopentoxy)phenoxy]-2,2-dimethylpentanoate Chemical group COC(=O)C(C)(C)CCCOC1=CC=C(OCCCC(C)(C)C(=O)OC)C(OC)=C1 IPFAQBQEPAFDSA-UHFFFAOYSA-N 0.000 claims 1
- AEWCEXJRJLVILL-UHFFFAOYSA-N methyl 5-[4-(5-methoxy-4,4-dimethyl-5-oxopentoxy)-3-methylphenoxy]-2,2-dimethylpentanoate Chemical group COC(=O)C(C)(C)CCCOC1=CC=C(OCCCC(C)(C)C(=O)OC)C(C)=C1 AEWCEXJRJLVILL-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- 230000001590 oxidative effect Effects 0.000 claims 1
- 125000000732 arylene group Chemical group 0.000 abstract description 7
- 239000003795 chemical substances by application Substances 0.000 abstract description 5
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000002844 melting Methods 0.000 description 19
- 230000008018 melting Effects 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 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 description 14
- 239000002904 solvent Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000002585 base Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000002168 alkylating agent Substances 0.000 description 5
- 229940100198 alkylating agent Drugs 0.000 description 5
- 235000012000 cholesterol Nutrition 0.000 description 5
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 229910000033 sodium borohydride Inorganic materials 0.000 description 4
- 239000012279 sodium borohydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 102000015779 HDL Lipoproteins Human genes 0.000 description 3
- 108010010234 HDL Lipoproteins Proteins 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 208000029078 coronary artery disease Diseases 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 150000002148 esters Chemical group 0.000 description 3
- OLYOMMYVUVXSJR-UHFFFAOYSA-N methyl 5-bromo-2,2-dimethylpentanoate Chemical compound COC(=O)C(C)(C)CCCBr OLYOMMYVUVXSJR-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000012805 post-processing Methods 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CXOWYJMDMMMMJO-UHFFFAOYSA-N 2,2-dimethylpentane Chemical compound CCCC(C)(C)C CXOWYJMDMMMMJO-UHFFFAOYSA-N 0.000 description 2
- CLFRCXCBWIQVRN-UHFFFAOYSA-N 2,5-dihydroxybenzaldehyde Chemical compound OC1=CC=C(O)C(C=O)=C1 CLFRCXCBWIQVRN-UHFFFAOYSA-N 0.000 description 2
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 2
- GTXDKCFFLZJGRZ-UHFFFAOYSA-N 2-(trifluoromethyl)benzene-1,4-diol Chemical compound OC1=CC=C(O)C(C(F)(F)F)=C1 GTXDKCFFLZJGRZ-UHFFFAOYSA-N 0.000 description 2
- GIMXWZYFIFOCBJ-UHFFFAOYSA-N 2-fluorobenzene-1,4-diol Chemical compound OC1=CC=C(O)C(F)=C1 GIMXWZYFIFOCBJ-UHFFFAOYSA-N 0.000 description 2
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 102000007330 LDL Lipoproteins Human genes 0.000 description 2
- 108010007622 LDL Lipoproteins Proteins 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000000306 component Substances 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- UKJFVOWPUXSBOM-UHFFFAOYSA-N hexane;oxolane Chemical compound C1CCOC1.CCCCCC UKJFVOWPUXSBOM-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- HMVQVKGTZKRYIU-UHFFFAOYSA-N methyl 5-[3-butanoyl-4-(5-methoxy-4,4-dimethyl-5-oxopentoxy)phenoxy]-2,2-dimethylpentanoate Chemical group CCCC(=O)C1=CC(OCCCC(C)(C)C(=O)OC)=CC=C1OCCCC(C)(C)C(=O)OC HMVQVKGTZKRYIU-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- PTBZRYBRVBHLCU-UHFFFAOYSA-N (2,5-dihydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=C(O)C(C(=O)C=2C=CC=CC=2)=C1 PTBZRYBRVBHLCU-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UYUMFCLCGXTSQA-UHFFFAOYSA-N 1,4-bis(3-chloropropoxy)benzene Chemical compound ClCCCOC1=CC=C(OCCCCl)C=C1 UYUMFCLCGXTSQA-UHFFFAOYSA-N 0.000 description 1
- SICXCTNDFJXFJV-UHFFFAOYSA-N 1,4-bis(4-chlorobutoxy)benzene Chemical compound ClCCCCOC1=CC=C(OCCCCCl)C=C1 SICXCTNDFJXFJV-UHFFFAOYSA-N 0.000 description 1
- CFQYIIXIHXUPQT-UHFFFAOYSA-N 1-(2,5-dihydroxyphenyl)propan-1-one Chemical compound CCC(=O)C1=CC(O)=CC=C1O CFQYIIXIHXUPQT-UHFFFAOYSA-N 0.000 description 1
- RSWCSEPYNHFPCS-UHFFFAOYSA-N 1-[4-[4-[4-(1-carboxycyclobutyl)butoxy]phenoxy]butyl]cyclobutane-1-carboxylic acid Chemical compound C=1C=C(OCCCCC2(CCC2)C(O)=O)C=CC=1OCCCCC1(C(=O)O)CCC1 RSWCSEPYNHFPCS-UHFFFAOYSA-N 0.000 description 1
- WLDWSGZHNBANIO-UHFFFAOYSA-N 2',5'-Dihydroxyacetophenone Chemical compound CC(=O)C1=CC(O)=CC=C1O WLDWSGZHNBANIO-UHFFFAOYSA-N 0.000 description 1
- BGUAPYRHJPWVEM-UHFFFAOYSA-N 2,2-dimethyl-4-pentenoic acid Chemical compound OC(=O)C(C)(C)CC=C BGUAPYRHJPWVEM-UHFFFAOYSA-N 0.000 description 1
- YTTWDTVYXAEAJA-UHFFFAOYSA-N 2,2-dimethyl-hexanoic acid Chemical compound CCCCC(C)(C)C(O)=O YTTWDTVYXAEAJA-UHFFFAOYSA-N 0.000 description 1
- GPASWZHHWPVSRG-UHFFFAOYSA-N 2,5-dimethylbenzene-1,4-diol Chemical compound CC1=CC(O)=C(C)C=C1O GPASWZHHWPVSRG-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- REFDOIWRJDGBHY-UHFFFAOYSA-N 2-bromobenzene-1,4-diol Chemical compound OC1=CC=C(O)C(Br)=C1 REFDOIWRJDGBHY-UHFFFAOYSA-N 0.000 description 1
- XCZKKZXWDBOGPA-UHFFFAOYSA-N 2-phenylbenzene-1,4-diol Chemical class OC1=CC=C(O)C(C=2C=CC=CC=2)=C1 XCZKKZXWDBOGPA-UHFFFAOYSA-N 0.000 description 1
- JIHQVMOXLWANLK-UHFFFAOYSA-N 5-[3-(benzenesulfonyl)-4-(4-carboxy-4-methylpentoxy)phenoxy]-2,2-dimethylpentanoic acid Chemical group OC(=O)C(C)(C)CCCOC1=CC=C(OCCCC(C)(C)C(O)=O)C(S(=O)(=O)C=2C=CC=CC=2)=C1 JIHQVMOXLWANLK-UHFFFAOYSA-N 0.000 description 1
- WGPOFMCIPHEKOE-UHFFFAOYSA-N 5-[4-(4-carboxy-4-methylpentoxy)-2,3,5-trimethylphenoxy]-2,2-dimethylpentanoic acid Chemical group CC1=CC(OCCCC(C)(C)C(O)=O)=C(C)C(C)=C1OCCCC(C)(C)C(O)=O WGPOFMCIPHEKOE-UHFFFAOYSA-N 0.000 description 1
- DRISVASVIYBWQE-UHFFFAOYSA-N 5-[4-(4-carboxy-4-methylpentoxy)-3-(1-hydroxypropyl)phenoxy]-2,2-dimethylpentanoic acid Chemical compound CCC(O)C1=CC(OCCCC(C)(C)C(O)=O)=CC=C1OCCCC(C)(C)C(O)=O DRISVASVIYBWQE-UHFFFAOYSA-N 0.000 description 1
- CHBBBYKTJSBOIL-UHFFFAOYSA-N 5-[4-(4-carboxy-4-methylpentoxy)-3-[hydroxy(phenyl)methyl]phenoxy]-2,2-dimethylpentanoic acid Chemical compound OC(=O)C(C)(C)CCCOC1=CC=C(OCCCC(C)(C)C(O)=O)C(C(O)C=2C=CC=CC=2)=C1 CHBBBYKTJSBOIL-UHFFFAOYSA-N 0.000 description 1
- BQYKOOXHUPHZMB-UHFFFAOYSA-N 5-[4-(4-carboxy-4-methylpentoxy)-3-phenylsulfanylphenoxy]-2,2-dimethylpentanoic acid Chemical group OC(=O)C(C)(C)CCCOC1=CC=C(OCCCC(C)(C)C(O)=O)C(SC=2C=CC=CC=2)=C1 BQYKOOXHUPHZMB-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical class [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000012503 blood component Substances 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 150000005690 diesters Chemical group 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- HBFXVTVOSLPOEY-UHFFFAOYSA-N ethoxyethane;2-propan-2-yloxypropane Chemical compound CCOCC.CC(C)OC(C)C HBFXVTVOSLPOEY-UHFFFAOYSA-N 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- KTZAZFWCITWBBQ-UHFFFAOYSA-N methyl 5-[3-formyl-4-(5-methoxy-4,4-dimethyl-5-oxopentoxy)phenoxy]-2,2-dimethylpentanoate Chemical compound COC(=O)C(C)(C)CCCOC1=CC=C(OCCCC(C)(C)C(=O)OC)C(C=O)=C1 KTZAZFWCITWBBQ-UHFFFAOYSA-N 0.000 description 1
- QCZITRDPGDRYTP-UHFFFAOYSA-N methyl 5-[4-(5-methoxy-4,4-dimethyl-5-oxopentoxy)-2,5-dimethylphenoxy]-2,2-dimethylpentanoate Chemical group COC(=O)C(C)(C)CCCOC1=CC(C)=C(OCCCC(C)(C)C(=O)OC)C=C1C QCZITRDPGDRYTP-UHFFFAOYSA-N 0.000 description 1
- DMMCKDBMXAINII-UHFFFAOYSA-N methyl 5-[4-(5-methoxy-4,4-dimethyl-5-oxopentoxy)-3-prop-1-enylphenoxy]-2,2-dimethylpentanoate Chemical compound COC(=O)C(C)(C)CCCOC1=CC=C(OCCCC(C)(C)C(=O)OC)C(C=CC)=C1 DMMCKDBMXAINII-UHFFFAOYSA-N 0.000 description 1
- WLHMRNQFDMHBMY-UHFFFAOYSA-N methyl 5-[4-acetyl-4-(5-methoxy-4,4-dimethyl-5-oxopentoxy)cyclohexa-1,5-dien-1-yl]oxy-2,2-dimethylpentanoate Chemical compound COC(=O)C(C)(C)CCCOC1=CCC(OCCCC(C)(C)C(=O)OC)(C(C)=O)C=C1 WLHMRNQFDMHBMY-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/23—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing hydroxy or O-metal groups
-
- 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
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/30—Unsaturated compounds
- C07C62/34—Unsaturated compounds containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/108,978 US4351950A (en) | 1980-01-02 | 1980-01-02 | Anti-arteriosclerotic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS56113722A JPS56113722A (en) | 1981-09-07 |
| JPH0132811B2 true JPH0132811B2 (d) | 1989-07-10 |
Family
ID=22325154
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18514380A Granted JPS56113722A (en) | 1980-01-02 | 1980-12-27 | Antiatherosclerotic compound |
| JP63151360A Granted JPS6470428A (en) | 1980-01-02 | 1988-06-21 | Compound and manufacture |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP63151360A Granted JPS6470428A (en) | 1980-01-02 | 1988-06-21 | Compound and manufacture |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US4351950A (d) |
| EP (1) | EP0032063B1 (d) |
| JP (2) | JPS56113722A (d) |
| AT (1) | ATE6586T1 (d) |
| DE (1) | DE3067072D1 (d) |
| HK (1) | HK69087A (d) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3125059A1 (de) * | 1981-06-26 | 1983-01-05 | Bayer Ag, 5090 Leverkusen | Dioxybenzoletherderivate, diese enthaltende arzneimittel, verfahren zu ihrer herstellung und ihre verwendung |
| IT1170214B (it) * | 1983-09-12 | 1987-06-03 | Crinos Industria Farmaco | Composizione farmaceutica per la cura delle arteriopatie periferiche |
| US4603142A (en) * | 1984-06-01 | 1986-07-29 | Wisconsin Alumni Research Foundation | Cholesterol lowering method of use |
| EP0175188A1 (de) * | 1984-09-11 | 1986-03-26 | Nihon Tokushu Noyaku Seizo K.K. | Carbamoylimidazol-Derivate |
| US4876279A (en) * | 1986-05-05 | 1989-10-24 | Merck & Co., Inc. | Antihypercholesterolemic compounds |
| US4847306A (en) * | 1986-05-05 | 1989-07-11 | Merck & Co., Inc. | Antihypercholesterolemic compounds |
| JPH03504092A (ja) * | 1988-07-11 | 1991-09-12 | イースト テネシー ステイト ユニバーシティ | 動脈硬化症の予知方法および治療方法 |
| US4937371A (en) * | 1989-02-21 | 1990-06-26 | Hoffmann-La Roche Inc. | Dihydroxynaphthalene derivatives |
| CA2074537A1 (en) * | 1991-07-29 | 1993-01-30 | Bruce E. Witzel | Catechol type non-steroidal drugs as 5-alpha reductase inhibitors |
| FR2738817B1 (fr) * | 1995-09-14 | 1997-10-17 | Adir | Nouveaux acides et esters 2,2-dimethyl-omega-phenoxy alcanoiques substitues, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| EP1366024A2 (en) | 2000-10-11 | 2003-12-03 | Esperion Therapeutics Inc. | Sulfoxide and bis-sulfoxide compounds and compositions for cholesterol management and related uses |
| CN101426763A (zh) * | 2000-10-11 | 2009-05-06 | 埃斯佩里安医疗公司 | 用于胆固醇治疗和相关应用的硫化物和二硫化物化合物和组合物 |
| MXPA03003021A (es) * | 2000-10-11 | 2003-07-14 | Esperion Therapeutics Inc | Compuestos de eter y composiciones para el control del colesterol y usos relacionados. |
| JP2006510687A (ja) * | 2002-12-20 | 2006-03-30 | ノボ ノルディスク アクティーゼルスカブ | 新規化合物、その調製および使用 |
| US7816385B2 (en) | 2002-12-20 | 2010-10-19 | High Point Pharmaceuticals, Llc | Dimeric dicarboxylic acid derivatives, their preparation and use |
| AU2003300439A1 (en) * | 2003-12-24 | 2005-08-03 | Esperion Therapeutics, Inc. | Sulfide and disulfide compounds and compositions for cholesterol management and related uses |
| WO2005068410A1 (en) * | 2003-12-24 | 2005-07-28 | Esperion Therapeutics, Inc. | Ether compounds and compositions for cholesterol management and related uses |
| US7846878B2 (en) | 2007-07-17 | 2010-12-07 | Halliburton Energy Services, Inc. | Friction reducer performance in water containing multivalent ions |
| WO2023102364A1 (en) * | 2021-12-02 | 2023-06-08 | Ecole Polytechnique Federale De Lausanne (Epfl) | Antiviral compounds, compositions and uses thereof |
| JP7266139B1 (ja) * | 2022-07-22 | 2023-04-27 | 本州化学工業株式会社 | 芳香族ビスエーテル化合物の製造方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE627791A (d) * | 1962-02-10 | |||
| GB1129175A (en) * | 1966-06-23 | 1968-10-02 | Pfizer Ltd | 4,4'-substituted biphenyls |
| US3674836A (en) * | 1968-05-21 | 1972-07-04 | Parke Davis & Co | 2,2-dimethyl-{11 -aryloxy-alkanoic acids and salts and esters thereof |
| FR2060088B1 (d) * | 1969-08-08 | 1974-08-30 | Orsymonde | |
| US3824293A (en) * | 1972-11-07 | 1974-07-16 | Union Carbide Corp | Bisthioethers |
| FR2331336A1 (fr) * | 1975-11-14 | 1977-06-10 | Rolland Sa A | Acides oxy-4,4' bis(phenoxy-2 alcanocarboxyliques), leurs derives et leur application comme medicament |
-
1980
- 1980-01-02 US US06/108,978 patent/US4351950A/en not_active Expired - Lifetime
- 1980-12-27 JP JP18514380A patent/JPS56113722A/ja active Granted
- 1980-12-30 DE DE8080304749T patent/DE3067072D1/de not_active Expired
- 1980-12-30 EP EP80304749A patent/EP0032063B1/en not_active Expired
- 1980-12-30 AT AT80304749T patent/ATE6586T1/de not_active IP Right Cessation
-
1987
- 1987-09-24 HK HK690/87A patent/HK69087A/en not_active IP Right Cessation
-
1988
- 1988-06-21 JP JP63151360A patent/JPS6470428A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| DE3067072D1 (en) | 1984-04-19 |
| EP0032063A2 (en) | 1981-07-15 |
| EP0032063A3 (en) | 1981-11-18 |
| JPS6470428A (en) | 1989-03-15 |
| JPS56113722A (en) | 1981-09-07 |
| ATE6586T1 (de) | 1984-03-15 |
| HK69087A (en) | 1987-10-02 |
| JPH0349899B2 (d) | 1991-07-31 |
| EP0032063B1 (en) | 1984-03-14 |
| US4351950A (en) | 1982-09-28 |
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