CA1145761A - Quinone derivatives - Google Patents
Quinone derivativesInfo
- Publication number
- CA1145761A CA1145761A CA000355168A CA355168A CA1145761A CA 1145761 A CA1145761 A CA 1145761A CA 000355168 A CA000355168 A CA 000355168A CA 355168 A CA355168 A CA 355168A CA 1145761 A CA1145761 A CA 1145761A
- Authority
- CA
- Canada
- Prior art keywords
- carbon atoms
- dimethoxy
- methyl
- group
- compound
- 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
- 150000004059 quinone derivatives Chemical class 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 48
- -1 silyloxymethyl Chemical group 0.000 claims abstract description 47
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 238000000034 method Methods 0.000 claims abstract description 39
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000001301 oxygen Substances 0.000 claims abstract description 21
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 230000001590 oxidative effect Effects 0.000 claims abstract description 8
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 8
- 150000003624 transition metals Chemical class 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000004849 alkoxymethyl group Chemical group 0.000 claims abstract description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 125000005042 acyloxymethyl group Chemical group 0.000 claims abstract description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract description 3
- JGPMMRGNQUBGND-UHFFFAOYSA-N idebenone Chemical compound COC1=C(OC)C(=O)C(CCCCCCCCCCO)=C(C)C1=O JGPMMRGNQUBGND-UHFFFAOYSA-N 0.000 claims description 5
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims description 4
- YYPSIPHPBFRNII-UHFFFAOYSA-N 2-(10-hydroxydecyl)-5,6-dimethoxy-3-methylphenol Chemical compound COC1=CC(C)=C(CCCCCCCCCCO)C(O)=C1OC YYPSIPHPBFRNII-UHFFFAOYSA-N 0.000 claims description 3
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- KJLPVJBOBGZWFW-UHFFFAOYSA-N N=[Co]=N.C(C=1C(O)=CC=CC1)=C=C=CC=1C(O)=CC=CC1 Chemical compound N=[Co]=N.C(C=1C(O)=CC=CC1)=C=C=CC=1C(O)=CC=CC1 KJLPVJBOBGZWFW-UHFFFAOYSA-N 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 abstract description 2
- 208000028169 periodontal disease Diseases 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 63
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- 239000000203 mixture Substances 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 12
- 239000013078 crystal Substances 0.000 description 10
- 238000007254 oxidation reaction Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 125000002252 acyl group Chemical group 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- 229910017052 cobalt Inorganic materials 0.000 description 9
- 239000010941 cobalt Substances 0.000 description 9
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 9
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 8
- 238000000605 extraction Methods 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- OQZGYMRYZAKXAF-UHFFFAOYSA-N 2-(4-methylcyclohexyl)acetic acid Chemical compound CC1CCC(CC(O)=O)CC1 OQZGYMRYZAKXAF-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 229940005561 1,4-benzoquinone Drugs 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000007800 oxidant agent Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- SAAXJJSVGGARNN-UHFFFAOYSA-N 10-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)decyl acetate Chemical compound COC1=C(OC)C(=O)C(CCCCCCCCCCOC(C)=O)=C(C)C1=O SAAXJJSVGGARNN-UHFFFAOYSA-N 0.000 description 4
- OYPKBMPPEBAPGW-UHFFFAOYSA-N 12-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)dodecyl acetate Chemical compound COC1=C(OC)C(=O)C(CCCCCCCCCCCCOC(C)=O)=C(C)C1=O OYPKBMPPEBAPGW-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 150000002431 hydrogen Chemical group 0.000 description 4
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- YFRFHMUSYMUXAV-UHFFFAOYSA-N 2-(20-hydroxyicosyl)-5,6-dimethoxy-3-methylphenol Chemical compound COC1=CC(C)=C(CCCCCCCCCCCCCCCCCCCCO)C(O)=C1OC YFRFHMUSYMUXAV-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004423 acyloxy group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000004678 hydrides Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 3
- 235000019796 monopotassium phosphate Nutrition 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 3
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 3
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 3
- 150000004053 quinones Chemical class 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- JSCUZAYKVZXKQE-JXMROGBWSA-N (2e)-1-bromo-3,7-dimethylocta-2,6-diene Chemical compound CC(C)=CCC\C(C)=C\CBr JSCUZAYKVZXKQE-JXMROGBWSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- HEZKISZUXFUMGR-UHFFFAOYSA-N 12-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)dodecyl acetate Chemical compound COC1=CC(C)=C(CCCCCCCCCCCCOC(C)=O)C(O)=C1OC HEZKISZUXFUMGR-UHFFFAOYSA-N 0.000 description 2
- SHRZCDBVLADXKH-UHFFFAOYSA-N 12-hydroxy-1-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)dodecan-1-one Chemical compound COC1=CC(C)=C(C(=O)CCCCCCCCCCCO)C(O)=C1OC SHRZCDBVLADXKH-UHFFFAOYSA-N 0.000 description 2
- VMHWZDULLBLUMS-UHFFFAOYSA-N 2-(12-hydroxydodecyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione Chemical compound COC1=C(OC)C(=O)C(CCCCCCCCCCCCO)=C(C)C1=O VMHWZDULLBLUMS-UHFFFAOYSA-N 0.000 description 2
- KRVZVBUKLVSUDM-UHFFFAOYSA-N 2-[5-(20-acetyloxyicosyl)-4-(carboxymethyl)-1,4-dihydroxy-2,3-dimethoxy-6-methylcyclohexa-2,5-dien-1-yl]acetic acid Chemical compound COC1=C(OC)C(O)(CC(O)=O)C(CCCCCCCCCCCCCCCCCCCCOC(C)=O)=C(C)C1(O)CC(O)=O KRVZVBUKLVSUDM-UHFFFAOYSA-N 0.000 description 2
- KCIZTNZGSBSSRM-UHFFFAOYSA-N 3,4,5-Trimethoxytoluene Chemical compound COC1=CC(C)=CC(OC)=C1OC KCIZTNZGSBSSRM-UHFFFAOYSA-N 0.000 description 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 2
- 101150041968 CDC13 gene Proteins 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical class CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 239000000043 antiallergic agent Substances 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229950005499 carbon tetrachloride Drugs 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000010531 catalytic reduction reaction Methods 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940113088 dimethylacetamide Drugs 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- UIXPTCZPFCVOQF-UHFFFAOYSA-N ubiquinone-0 Chemical compound COC1=C(OC)C(=O)C(C)=CC1=O UIXPTCZPFCVOQF-UHFFFAOYSA-N 0.000 description 2
- XXVVHKXAGYYXJB-UHFFFAOYSA-N (12-chloro-12-oxododecyl) acetate Chemical compound CC(=O)OCCCCCCCCCCCC(Cl)=O XXVVHKXAGYYXJB-UHFFFAOYSA-N 0.000 description 1
- KGIZSOWPDDQVIC-UHFFFAOYSA-N (18-chloro-18-oxooctadecyl) acetate Chemical compound CC(=O)OCCCCCCCCCCCCCCCCCC(Cl)=O KGIZSOWPDDQVIC-UHFFFAOYSA-N 0.000 description 1
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OSVNAZHUSIZAKH-UHFFFAOYSA-N 1-(2-hydroxy-3,4,6-trimethylphenyl)hexane-1,6-diol Chemical compound CC1=CC(C)=C(C(O)CCCCCO)C(O)=C1C OSVNAZHUSIZAKH-UHFFFAOYSA-N 0.000 description 1
- RKMNQXFECVRTNI-UHFFFAOYSA-N 1-methylcyclohexa-2,4-dien-1-ol Chemical compound CC1(O)CC=CC=C1 RKMNQXFECVRTNI-UHFFFAOYSA-N 0.000 description 1
- ZBEIUPHVFHOFQL-UHFFFAOYSA-N 10-(2-hydroxy-3,4,6-trimethylphenyl)decanoic acid Chemical compound CC1=CC(C)=C(CCCCCCCCCC(O)=O)C(O)=C1C ZBEIUPHVFHOFQL-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C66/00—Quinone carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/26—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of hydroxy or O-metal groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
- C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C07C46/02—Preparation of quinones by oxidation giving rise to quinoid structures
- C07C46/06—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring
- C07C46/08—Preparation of quinones by oxidation giving rise to quinoid structures of at least one hydroxy group on a six-membered aromatic ring with molecular oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/26—Quinones containing groups having oxygen atoms singly bound to carbon atoms
- C07C50/28—Quinones containing groups having oxygen atoms singly bound to carbon atoms with monocyclic quinoid structure
-
- 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
-
- 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
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP82381/1979 | 1979-06-28 | ||
| JP8238179A JPS567734A (en) | 1979-06-28 | 1979-06-28 | Preparation of quinone derivative |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1145761A true CA1145761A (en) | 1983-05-03 |
Family
ID=13772994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000355168A Expired CA1145761A (en) | 1979-06-28 | 1980-06-30 | Quinone derivatives |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4559177A (enExample) |
| JP (1) | JPS567734A (enExample) |
| CA (1) | CA1145761A (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56147746A (en) * | 1980-04-15 | 1981-11-16 | Takeda Chem Ind Ltd | Quinones and their preparation |
| JPS6078932A (ja) * | 1983-10-03 | 1985-05-04 | Sumitomo Chem Co Ltd | ２，３−ジ低級アルコキシ−５−低級アルキル−１，４−ベンゾキノンの製造法 |
| JPS60166640A (ja) * | 1984-01-31 | 1985-08-29 | Sagami Chem Res Center | アルコキシ−ｐ−ベンゾキノンの製造法 |
| MX9203040A (es) * | 1984-08-01 | 1992-07-31 | Takeda Chemical Industries Ltd | Derivados de quinona y composicion farmaceutica que los contiene. |
| US5304658A (en) * | 1984-08-01 | 1994-04-19 | Takeda Chemical Industries, Ltd. | Quinone derivatives, their production and use |
| ATE64921T1 (de) * | 1985-04-08 | 1991-07-15 | Takeda Chemical Industries Ltd | Benzochinonderivate, ihre herstellung und verwendung. |
| JPH0687940B2 (ja) * | 1985-07-01 | 1994-11-09 | 三菱重工業株式会社 | 液体乾燥剤の再生方法 |
| ES2051841T3 (es) * | 1987-04-27 | 1994-07-01 | Takeda Chemical Industries Ltd | Reduccion de esteres carboxilicos. |
| US4914217A (en) * | 1987-12-18 | 1990-04-03 | Hoffmann-La Roche Inc. | Asymmetric synthesis of natural vitamin E |
| US4855085A (en) * | 1987-12-18 | 1989-08-08 | Hoffmann-La Roche Inc. | Asymmetric synthesis of natural vitamin E |
| SE464853B (sv) * | 1988-08-01 | 1991-06-24 | Ahlstroem Foeretagen | Foerfarande foer avfuktning av en gas, speciellt luft |
| DE3842014A1 (de) * | 1988-12-14 | 1990-06-21 | Bayer Ag | Verfahren zur herstellung von sulfogruppenfreien triphenylmethanfarbstoffen |
| EP0560568A3 (en) * | 1992-03-13 | 1994-06-29 | Takeda Chemical Industries Ltd | Hydroquinone derivatives and intermediates for production thereof |
| US5318993A (en) * | 1993-04-16 | 1994-06-07 | Bristol-Myers Squibb Company | Antihyperlipidemic benzoquinones |
| US20020032160A1 (en) * | 1995-02-24 | 2002-03-14 | Nyce Jonathan W. | Compositions & formulations with an epiandrosterone or a ubiquinone & kits & their use for treatment of asthma symptoms & for reducing adenosine/adenosine receptor levels |
| US5660835A (en) * | 1995-02-24 | 1997-08-26 | East Carolina University | Method of treating adenosine depletion |
| US7713546B1 (en) * | 2001-04-03 | 2010-05-11 | Soft Gel Technologies, Inc. | Corosolic acid formulation and its application for weight-loss management and blood sugar balance |
| KR100398055B1 (ko) * | 2000-11-23 | 2003-09-19 | 한국화학연구원 | 항산화 활성을 가지는 퀴논 화합물 |
| WO2005032521A2 (en) * | 2003-10-02 | 2005-04-14 | Collegium Pharmaceutical, Inc. | Non-flammable topical anesthetic liquid aerosols |
| US20060188449A1 (en) * | 2003-10-03 | 2006-08-24 | Jane Hirsh | Topical aerosol foams |
| US20060051435A1 (en) * | 2004-08-19 | 2006-03-09 | Udell Ronald G | Nutritional supplement for body fat reduction |
| EA035619B1 (ru) | 2005-06-01 | 2020-07-16 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Композиции для использования в способе лечения митохондриальных нарушений |
| JP2009508867A (ja) * | 2005-09-15 | 2009-03-05 | エジソン ファーマシューティカルズ， インコーポレイテッド | ミトコンドリア病および関連した様態の治療ならびにエネルギーバイオマーカーの調節のための酸化還元活性治療剤のテイル改変体 |
| EP1986636B1 (en) | 2006-02-22 | 2013-04-24 | Edison Pharmaceuticals, Inc. | Phenol and 1,4-benzoquinone derivatives for use in the treatment of mitochondrial diseases |
| US20080268039A1 (en) * | 2007-03-06 | 2008-10-30 | Soft Gel Technologies, Inc. | Loquat compositions |
| US7528271B2 (en) * | 2007-05-16 | 2009-05-05 | Bergen Teknologioverforing As | Intermediates, process for their preparation and synthesis of 1,4-benzoquiones |
| US8652443B2 (en) * | 2008-02-14 | 2014-02-18 | Precision Dermatology, Inc. | Foamable microemulsion compositions for topical administration |
| EP2344142B1 (en) | 2008-09-10 | 2024-06-26 | PTC Therapeutics, Inc. | Treatment of pervasive developmental disorders with redox-active therapeutics |
| US8263094B2 (en) * | 2008-09-23 | 2012-09-11 | Eastman Chemical Company | Esters of 4,5-disubstituted-oxy-2-methyl-3,6-dioxo-cyclohexa-1,4-dienyl alkyl acids and preparation thereof |
| US20170117214A1 (en) | 2009-01-05 | 2017-04-27 | Amkor Technology, Inc. | Semiconductor device with through-mold via |
| EP3389646A1 (en) | 2015-12-17 | 2018-10-24 | BioElectron Technology Corporation | Flouroalkyl, flouroalkoxy, phenoxy, heteroaryloxy, alkoxy, and amine 1,4-benzoquinone derivatives for treatment of oxidative stress disorders |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1793183B1 (de) * | 1968-08-13 | 1972-03-16 | Basf Ag | Verfahren zur Herstellung von Trimethyl-p-benzochinon |
| JPS4899130A (enExample) * | 1972-04-05 | 1973-12-15 | ||
| US3966776A (en) * | 1973-03-09 | 1976-06-29 | Takasago Perfumery Co., Ltd. | Process for preparing parabenzoquinones |
| JPS5014641A (enExample) * | 1973-06-15 | 1975-02-15 | ||
| US3859317A (en) * | 1973-09-28 | 1975-01-07 | Goodyear Tire & Rubber | Process of preparing p-benzoquinone |
| GB1455753A (en) * | 1974-01-08 | 1976-11-17 | Shell Int Research | Process for de preparation of p-quinones |
| FR2268779A1 (en) * | 1974-04-23 | 1975-11-21 | Rhone Poulenc Ind | Trimethyl-para-benzoquinone prepn. - by oxidn. of 2,3,5-trimethyl-phenol in presence of complex salts of cobalt and Schiff's bases |
| GB1468575A (en) * | 1974-04-24 | 1977-03-30 | Shell Int Res Mij Bf | Process for the preparation of p-quinones |
| JPS5919930B2 (ja) * | 1974-05-02 | 1984-05-09 | 武田薬品工業株式会社 | キノン酸誘導体の製造法 |
| JPS51128932A (en) * | 1975-04-30 | 1976-11-10 | Takeda Chem Ind Ltd | Organic compounds |
| JPS604164B2 (ja) * | 1975-09-29 | 1985-02-01 | エーザイ株式会社 | 補酵素ｑ類化合物の合成法 |
| DE2706842C2 (de) * | 1976-02-19 | 1985-10-24 | Shell Internationale Research Maatschappij B.V., Den Haag | Verfahren zur Herstellung von 2,3,5-Trimethylhydrochinon |
-
1979
- 1979-06-28 JP JP8238179A patent/JPS567734A/ja active Granted
-
1980
- 1980-06-30 CA CA000355168A patent/CA1145761A/en not_active Expired
- 1980-06-30 US US06/164,018 patent/US4559177A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4559177A (en) | 1985-12-17 |
| JPS633854B2 (enExample) | 1988-01-26 |
| JPS567734A (en) | 1981-01-27 |
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