JPH0137384B2 - - Google Patents
Info
- Publication number
- JPH0137384B2 JPH0137384B2 JP20657686A JP20657686A JPH0137384B2 JP H0137384 B2 JPH0137384 B2 JP H0137384B2 JP 20657686 A JP20657686 A JP 20657686A JP 20657686 A JP20657686 A JP 20657686A JP H0137384 B2 JPH0137384 B2 JP H0137384B2
- Authority
- JP
- Japan
- Prior art keywords
- free form
- compound
- formula
- singlet
- nuclear
- 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 description 97
- AZQWKYJCGOJGHM-UHFFFAOYSA-N para-benzoquinone Natural products O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 36
- -1 quinone compound Chemical class 0.000 claims description 35
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 132
- 229910052739 hydrogen Inorganic materials 0.000 description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- 229910052727 yttrium Inorganic materials 0.000 description 49
- 239000000243 solution Substances 0.000 description 47
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
- 238000002844 melting Methods 0.000 description 39
- 230000008018 melting Effects 0.000 description 39
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
- 238000000921 elemental analysis Methods 0.000 description 35
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 34
- 238000000034 method Methods 0.000 description 33
- 238000006243 chemical reaction Methods 0.000 description 32
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 29
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 27
- 238000006722 reduction reaction Methods 0.000 description 27
- 238000000862 absorption spectrum Methods 0.000 description 26
- 229910002091 carbon monoxide Inorganic materials 0.000 description 25
- 239000000284 extract Substances 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000003756 stirring Methods 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 23
- 229910052799 carbon Inorganic materials 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- 239000013078 crystal Substances 0.000 description 18
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 239000010410 layer Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 238000010898 silica gel chromatography Methods 0.000 description 12
- 230000001476 alcoholic effect Effects 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 10
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 10
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 10
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 238000007254 oxidation reaction Methods 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 9
- 229910052805 deuterium Inorganic materials 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 150000002978 peroxides Chemical class 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- OQZGYMRYZAKXAF-UHFFFAOYSA-N 2-(4-methylcyclohexyl)acetic acid Chemical compound CC1CCC(CC(O)=O)CC1 OQZGYMRYZAKXAF-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 8
- 229910052725 zinc Inorganic materials 0.000 description 8
- 239000011701 zinc Substances 0.000 description 8
- 229940005561 1,4-benzoquinone Drugs 0.000 description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 150000004702 methyl esters Chemical class 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- RUSKPDLSOBIOHZ-UHFFFAOYSA-N 6-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)hexanoic acid Chemical compound CC1=C(C)C(=O)C(CCCCCC(O)=O)=C(C)C1=O RUSKPDLSOBIOHZ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 229910000497 Amalgam Inorganic materials 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- 239000007800 oxidant agent Substances 0.000 description 6
- PFKQKFBAEWIGCO-UHFFFAOYSA-N 6-(2-hydroxy-3,4,6-trimethylphenyl)-6-oxohexanoic acid Chemical compound CC1=CC(C)=C(C(=O)CCCCC(O)=O)C(O)=C1C PFKQKFBAEWIGCO-UHFFFAOYSA-N 0.000 description 5
- 235000019502 Orange oil Nutrition 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 239000010502 orange oil Substances 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 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 4
- OGRAOKJKVGDSFR-UHFFFAOYSA-N 2,3,5-trimethylphenol Chemical compound CC1=CC(C)=C(C)C(O)=C1 OGRAOKJKVGDSFR-UHFFFAOYSA-N 0.000 description 4
- RBFYYQXCHBEGHE-UHFFFAOYSA-N 6-(2,5-dihydroxy-3,4,6-trimethylphenyl)hexanoic acid Chemical compound CC1=C(C)C(O)=C(CCCCCC(O)=O)C(C)=C1O RBFYYQXCHBEGHE-UHFFFAOYSA-N 0.000 description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 102000014944 Lysosome-Associated Membrane Glycoproteins Human genes 0.000 description 4
- 108010064171 Lysosome-Associated Membrane Glycoproteins Proteins 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 238000010531 catalytic reduction reaction Methods 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 4
- 235000012239 silicon dioxide Nutrition 0.000 description 4
- 229910001923 silver oxide Inorganic materials 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- HGTCXDIEXCZKPN-UHFFFAOYSA-N 10-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)-10-oxodecanoic acid Chemical compound COC1=CC(C)=C(C(=O)CCCCCCCCC(O)=O)C(O)=C1OC HGTCXDIEXCZKPN-UHFFFAOYSA-N 0.000 description 3
- CHKYMIHNCJOREQ-UHFFFAOYSA-N 2-(6-hydroxyhexyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione Chemical compound CC1=C(C)C(=O)C(CCCCCCO)=C(C)C1=O CHKYMIHNCJOREQ-UHFFFAOYSA-N 0.000 description 3
- KCIZTNZGSBSSRM-UHFFFAOYSA-N 3,4,5-Trimethoxytoluene Chemical compound COC1=CC(C)=CC(OC)=C1OC KCIZTNZGSBSSRM-UHFFFAOYSA-N 0.000 description 3
- YPXATGFVVQQCBY-UHFFFAOYSA-N 6-(2-hydroxy-3,4,6-trimethylphenyl)hexanoic acid Chemical compound CC1=CC(C)=C(CCCCCC(O)=O)C(O)=C1C YPXATGFVVQQCBY-UHFFFAOYSA-N 0.000 description 3
- BJFOQDFWWQWXCE-UHFFFAOYSA-N 6-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)hexanoic acid Chemical compound COC1=CC(C)=C(CCCCCC(O)=O)C(O)=C1OC BJFOQDFWWQWXCE-UHFFFAOYSA-N 0.000 description 3
- NYCZXGXBAJEDRI-UHFFFAOYSA-N 6-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-6-oxohexanoic acid Chemical compound COC1=C(OC)C(=O)C(C(=O)CCCCC(O)=O)=C(C)C1=O NYCZXGXBAJEDRI-UHFFFAOYSA-N 0.000 description 3
- BCAUMTMVEROYKS-UHFFFAOYSA-N 6-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)hexanoic acid Chemical compound COC1=C(OC)C(=O)C(CCCCCC(O)=O)=C(C)C1=O BCAUMTMVEROYKS-UHFFFAOYSA-N 0.000 description 3
- ZTHQKHODYQDRNQ-UHFFFAOYSA-N 6-oxo-6-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dien-1-yl)hexanoic acid Chemical compound CC1=C(C)C(=O)C(C(=O)CCCCC(O)=O)=C(C)C1=O ZTHQKHODYQDRNQ-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 125000002252 acyl group Chemical group 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 230000003308 immunostimulating effect Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 230000002132 lysosomal effect Effects 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- YHCCZTKUBLEWJH-UHFFFAOYSA-N methyl 10-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)decanoate Chemical compound COC(=O)CCCCCCCCCC1=C(C)C(=O)C(OC)=C(OC)C1=O YHCCZTKUBLEWJH-UHFFFAOYSA-N 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
- 239000002244 precipitate Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 230000001105 regulatory effect Effects 0.000 description 3
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- RKROOHPBHKLQMK-UHFFFAOYSA-N 1-(2,5-dihydroxy-3,4,6-trimethylphenyl)-6-hydroxyhexan-1-one Chemical compound CC1=C(C)C(O)=C(C(=O)CCCCCO)C(C)=C1O RKROOHPBHKLQMK-UHFFFAOYSA-N 0.000 description 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 2
- LRQXFYIZXFGRGB-UHFFFAOYSA-N 10-(2-hydroxy-3,4,6-trimethylphenyl)-10-oxodecanoic acid Chemical compound CC1=CC(C)=C(C(=O)CCCCCCCCC(O)=O)C(O)=C1C LRQXFYIZXFGRGB-UHFFFAOYSA-N 0.000 description 2
- 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 2
- QFHSYPPEQOEFRI-UHFFFAOYSA-N 10-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)decanoic acid Chemical compound COC1=C(OC)C(=O)C(CCCCCCCCCC(O)=O)=C(C)C1=O QFHSYPPEQOEFRI-UHFFFAOYSA-N 0.000 description 2
- KDFSPVDOISNFFO-UHFFFAOYSA-N 2-(4-hydroxybutyl)-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione Chemical compound COC1=C(OC)C(=O)C(CCCCO)=C(C)C1=O KDFSPVDOISNFFO-UHFFFAOYSA-N 0.000 description 2
- HYCSVAYWEHUEOJ-UHFFFAOYSA-N 2-(6-hydroxyhexyl)-3,5,6-trimethylphenol Chemical compound CC1=CC(C)=C(CCCCCCO)C(O)=C1C HYCSVAYWEHUEOJ-UHFFFAOYSA-N 0.000 description 2
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 236TMPh Natural products CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 2
- LLZIRHCBBMGEEM-UHFFFAOYSA-N 4-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)-4-oxobutanoic acid Chemical compound COC1=CC(C)=C(C(=O)CCC(O)=O)C(O)=C1OC LLZIRHCBBMGEEM-UHFFFAOYSA-N 0.000 description 2
- DGETWALUVHDTGC-UHFFFAOYSA-N 4-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)butanoic acid Chemical compound COC1=CC(C)=C(CCCC(O)=O)C(O)=C1OC DGETWALUVHDTGC-UHFFFAOYSA-N 0.000 description 2
- BCIGBQHFDOYUDK-UHFFFAOYSA-N 4-(4,5-dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)butanoic acid Chemical compound COC1=C(OC)C(=O)C(CCCC(O)=O)=C(C)C1=O BCIGBQHFDOYUDK-UHFFFAOYSA-N 0.000 description 2
- ZIIUIZJLNRHTKM-UHFFFAOYSA-N 6-(2-hydroxy-3,4-dimethoxy-6-methylphenyl)-6-oxohexanoic acid Chemical compound COC1=CC(C)=C(C(=O)CCCCC(O)=O)C(O)=C1OC ZIIUIZJLNRHTKM-UHFFFAOYSA-N 0.000 description 2
- MVLOLUZRGUDQDK-UHFFFAOYSA-N 7-(2-hydroxy-3,4,6-trimethylphenyl)-7-oxoheptanoic acid Chemical compound CC1=CC(C)=C(C(=O)CCCCCC(O)=O)C(O)=C1C MVLOLUZRGUDQDK-UHFFFAOYSA-N 0.000 description 2
- XECCNUPAIDSSGF-UHFFFAOYSA-N 7-(2-hydroxy-3,4,6-trimethylphenyl)heptanoic acid Chemical compound CC1=CC(C)=C(CCCCCCC(O)=O)C(O)=C1C XECCNUPAIDSSGF-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
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- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical compound CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/573,158 US4139545A (en) | 1974-05-02 | 1975-04-30 | Aralkyl carboxylic acid compounds |
| US573158 | 2000-05-19 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP128076A Division JPS51128932A (en) | 1975-04-30 | 1976-01-01 | Organic compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63264436A JPS63264436A (ja) | 1988-11-01 |
| JPH0137384B2 true JPH0137384B2 (ko) | 1989-08-07 |
Family
ID=24290879
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP128076A Granted JPS51128932A (en) | 1975-04-30 | 1976-01-01 | Organic compounds |
| JP20657586A Granted JPS63264441A (ja) | 1975-04-30 | 1986-09-01 | キノン誘導体の製造法 |
| JP20657686A Granted JPS63264436A (ja) | 1975-04-30 | 1986-09-01 | キノン化合物の製造法 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP128076A Granted JPS51128932A (en) | 1975-04-30 | 1976-01-01 | Organic compounds |
| JP20657586A Granted JPS63264441A (ja) | 1975-04-30 | 1986-09-01 | キノン誘導体の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (3) | JPS51128932A (ko) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS567734A (en) * | 1979-06-28 | 1981-01-27 | Takeda Chem Ind Ltd | Preparation of quinone derivative |
| JPS5697223A (en) * | 1979-12-30 | 1981-08-05 | Takeda Chem Ind Ltd | Tissue metabolism activator |
| JPS5738744A (en) * | 1980-08-19 | 1982-03-03 | Takeda Chem Ind Ltd | Quinone derivative and its preparation |
| JPS57131735A (en) * | 1981-02-09 | 1982-08-14 | Takeda Chem Ind Ltd | Preparation of quinones |
| JPS5877839A (ja) * | 1981-11-02 | 1983-05-11 | Takeda Chem Ind Ltd | 安定な微細結晶およびその製造法 |
| JPS58174343A (ja) * | 1982-04-06 | 1983-10-13 | Takeda Chem Ind Ltd | ベンゾキノン誘導体 |
| WO1986000887A1 (en) * | 1984-08-01 | 1986-02-13 | Takeda Chemical Industries, Ltd. | Quinone derivatives, process for their preparation, and medicinal composition containing the same |
| JP2570806B2 (ja) * | 1987-04-27 | 1997-01-16 | 武田薬品工業株式会社 | エステル化合物の還元方法 |
| EP0788793A1 (en) | 1996-02-01 | 1997-08-13 | Takeda Chemical Industries, Ltd. | Idebenone for the treatment of dementia |
| KR100398055B1 (ko) * | 2000-11-23 | 2003-09-19 | 한국화학연구원 | 항산화 활성을 가지는 퀴논 화합물 |
| EP2203162B1 (en) * | 2007-09-26 | 2017-11-08 | Indiana University Research and Technology Corporation | Benzoquinone derivative e3330 in combination with chemotherapeutic agents for the treatment of cancer and angiogenesis |
| PL2108366T3 (pl) | 2008-04-09 | 2012-03-30 | Santhera Pharmaceuticals Schweiz Ag | Idebenon stosowany w leczeniu chorób układu oddechowego towarzyszących dystrofii mięśniowej |
| EP2246048A1 (en) | 2009-04-30 | 2010-11-03 | Santhera Pharmaceuticals (Schweiz) AG | Quinone derivative 2,3-dimethoxy-5-methyl-6-(10-hydroxydecyl)-1,4-benzoquinone for the treatment of primary progressive multiple sclerosis |
| EP2606022A2 (en) | 2010-08-16 | 2013-06-26 | Santhera Pharmaceuticals (Schweiz) AG | Novel benzoquinone derivatives and use thereof as modulators of mitochondrial function |
| PT2605769T (pt) | 2010-08-16 | 2016-11-02 | Santhera Pharmaceuticals (Schweiz) Ag | Derivados benziquinona como modeladores da função mitocondrial |
| CN108084006B (zh) * | 2017-10-30 | 2020-12-29 | 浙江新和成药业有限公司 | 一种三甲基苯醌及三甲基氢醌的制备方法 |
-
1976
- 1976-01-01 JP JP128076A patent/JPS51128932A/ja active Granted
-
1986
- 1986-09-01 JP JP20657586A patent/JPS63264441A/ja active Granted
- 1986-09-01 JP JP20657686A patent/JPS63264436A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS623134B2 (ko) | 1987-01-23 |
| JPS63264436A (ja) | 1988-11-01 |
| JPH0114215B2 (ko) | 1989-03-10 |
| JPS51128932A (en) | 1976-11-10 |
| JPS63264441A (ja) | 1988-11-01 |
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