JPS63501564A - ラセミ・ノルジヒドログアヤレチン酸および中間体 - Google Patents
ラセミ・ノルジヒドログアヤレチン酸および中間体Info
- Publication number
- JPS63501564A JPS63501564A JP60505283A JP50528385A JPS63501564A JP S63501564 A JPS63501564 A JP S63501564A JP 60505283 A JP60505283 A JP 60505283A JP 50528385 A JP50528385 A JP 50528385A JP S63501564 A JPS63501564 A JP S63501564A
- Authority
- JP
- Japan
- Prior art keywords
- aralkyl
- lower alkyl
- enantiomers
- tables
- formulas
- 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.)
- Granted
Links
- HCZKYJDFEPMADG-UHFFFAOYSA-N erythro-nordihydroguaiaretic acid Natural products C=1C=C(O)C(O)=CC=1CC(C)C(C)CC1=CC=C(O)C(O)=C1 HCZKYJDFEPMADG-UHFFFAOYSA-N 0.000 title description 24
- 239000000543 intermediate Substances 0.000 title description 11
- HCZKYJDFEPMADG-TXEJJXNPSA-N masoprocol Chemical compound C([C@H](C)[C@H](C)CC=1C=C(O)C(O)=CC=1)C1=CC=C(O)C(O)=C1 HCZKYJDFEPMADG-TXEJJXNPSA-N 0.000 title description 8
- 229960003951 masoprocol Drugs 0.000 title description 4
- 239000000203 mixture Substances 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 38
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 32
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 239000007858 starting material Substances 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 17
- -1 butaneoxy Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000012467 final product Substances 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 3
- 239000006210 lotion Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000002674 ointment Substances 0.000 claims description 3
- 239000000344 soap Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims 8
- 239000007795 chemical reaction product Substances 0.000 claims 3
- 208000002925 dental caries Diseases 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-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
- 150000002009 diols Chemical class 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000001273 butane Substances 0.000 description 6
- 125000005594 diketone group Chemical group 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- XOJVVFBFDXDTEG-UHFFFAOYSA-N pristane Chemical compound CC(C)CCCC(C)CCCC(C)CCCC(C)C XOJVVFBFDXDTEG-UHFFFAOYSA-N 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 239000012280 lithium aluminium hydride Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000003638 chemical reducing agent Substances 0.000 description 3
- 230000020335 dealkylation Effects 0.000 description 3
- 238000006900 dealkylation reaction Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 235000020030 perry Nutrition 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 244000073231 Larrea tridentata Species 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000004678 hydrides Chemical group 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- ZMQAAUBTXCXRIC-UHFFFAOYSA-N safrole Chemical compound C=CCC1=CC=C2OCOC2=C1 ZMQAAUBTXCXRIC-UHFFFAOYSA-N 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 125000000026 trimethylsilyl group Chemical class [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- SPBNPRXRUYBFDV-UHFFFAOYSA-N 1,4-bis(3,4-dimethoxyphenyl)-2,3-dimethylbutane-1,4-dione Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)C(C)C(C)C(=O)C1=CC=C(OC)C(OC)=C1 SPBNPRXRUYBFDV-UHFFFAOYSA-N 0.000 description 1
- OPAORDVBZRVVNQ-RNQWEJQRSA-N 4-[(z,2r)-4-(4-hydroxy-3-methoxyphenyl)-2,3-dimethylbut-3-enyl]-2-methoxyphenol Chemical compound C1=C(O)C(OC)=CC(C[C@@H](C)C(\C)=C/C=2C=C(OC)C(O)=CC=2)=C1 OPAORDVBZRVVNQ-RNQWEJQRSA-N 0.000 description 1
- JMYXNUMGPRHHBC-UHFFFAOYSA-N 4-[4-(3,4-dihydroxyphenyl)butyl]benzene-1,2-diol Chemical compound C1=C(O)C(O)=CC=C1CCCCC1=CC=C(O)C(O)=C1 JMYXNUMGPRHHBC-UHFFFAOYSA-N 0.000 description 1
- RZJYHDXBLHCFGB-UHFFFAOYSA-N 4-[4-(3,4-dimethoxyphenyl)-1,4-dimethoxy-2,3-dimethylbutyl]-1,2-dimethoxybenzene Chemical compound C=1C=C(OC)C(OC)=CC=1C(OC)C(C)C(C)C(OC)C1=CC=C(OC)C(OC)=C1 RZJYHDXBLHCFGB-UHFFFAOYSA-N 0.000 description 1
- VJPNFMCNTKHVTR-UHFFFAOYSA-N 4-butyl-1,2-dimethoxybenzene Chemical compound CCCCC1=CC=C(OC)C(OC)=C1 VJPNFMCNTKHVTR-UHFFFAOYSA-N 0.000 description 1
- LAVPWYRENKSWJM-UHFFFAOYSA-N 4-butylbenzene-1,2-diol Chemical compound CCCCC1=CC=C(O)C(O)=C1 LAVPWYRENKSWJM-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- ADFOLUXMYYCTRR-ZIAGYGMSSA-N Dihydroguaiaretic acid Natural products C1=C(O)C(OC)=CC(C[C@@H](C)[C@H](C)CC=2C=C(OC)C(O)=CC=2)=C1 ADFOLUXMYYCTRR-ZIAGYGMSSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 241000935061 Larrea Species 0.000 description 1
- 244000122992 Larrea divaricata Species 0.000 description 1
- 235000002828 Larrea divaricata Nutrition 0.000 description 1
- 235000006173 Larrea tridentata Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- PCSMJKASWLYICJ-UHFFFAOYSA-N Succinic aldehyde Chemical class O=CCCC=O PCSMJKASWLYICJ-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 235000021028 berry Nutrition 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000012605 creosote bush Nutrition 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000002778 food additive Substances 0.000 description 1
- 235000013373 food additive Nutrition 0.000 description 1
- 235000019261 food antioxidant Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229930013686 lignan Natural products 0.000 description 1
- 150000005692 lignans Chemical class 0.000 description 1
- 235000009408 lignans Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- ADFOLUXMYYCTRR-OKILXGFUSA-N meso-dihydroguaiaretic acid Chemical compound C1=C(O)C(OC)=CC(C[C@H](C)[C@H](C)CC=2C=C(OC)C(O)=CC=2)=C1 ADFOLUXMYYCTRR-OKILXGFUSA-N 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000001301 oxygen 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
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000006257 total synthesis reaction Methods 0.000 description 1
- 230000010415 tropism Effects 0.000 description 1
Classifications
-
- 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
- C07C43/205—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring
- C07C43/2055—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring the aromatic ring being a non-condensed ring containing more than one ether bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/15—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings with all hydroxy groups on non-condensed rings, e.g. phenylphenol
- C07C39/16—Bis-(hydroxyphenyl) alkanes; Tris-(hydroxyphenyl)alkanes
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
- Detergent Compositions (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/436,444 US4562298A (en) | 1982-10-25 | 1982-10-25 | Optically active nordihydroguaiaretic acid and intermediates |
| PCT/US1985/002164 WO1987002661A1 (en) | 1982-10-25 | 1985-11-04 | Racemic nordihydroguaiaretic acid and intermediates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS63501564A true JPS63501564A (ja) | 1988-06-16 |
| JPH034530B2 JPH034530B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-01-23 |
Family
ID=23732423
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60505283A Granted JPS63501564A (ja) | 1982-10-25 | 1985-11-04 | ラセミ・ノルジヒドログアヤレチン酸および中間体 |
Country Status (8)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011190267A (ja) * | 2005-01-05 | 2011-09-29 | National Defense Education & Research Foundation | ウリジン２リン酸（ｕｄｐ）−グルクロン酸転移酵素２ｂ（ｕｇｔ２ｂ）の抑制剤及び促進剤 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5409690A (en) * | 1993-06-23 | 1995-04-25 | Chemex Pharmaceuticals, Inc. | Treatment of multidrug resistant diseases in cancer cell by potentiating with masoprocol |
| US5827898A (en) * | 1996-10-07 | 1998-10-27 | Shaman Pharmaceuticals, Inc. | Use of bisphenolic compounds to treat type II diabetes |
| MX391317B (es) | 2017-02-17 | 2025-03-21 | Promotora Tecnica Ind S A De C V | Composicion mejorada a base de acido norhidroguayaretico. |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2421117A (en) * | 1943-03-06 | 1947-05-27 | Univ Minnesota | Process for producing plant extracts |
| US2456443A (en) * | 1946-12-06 | 1948-12-14 | Wyeth Corp | Process for preparing nordihydroguaiaretic acid and intermediates |
| US2644822A (en) * | 1949-08-26 | 1953-07-07 | Sulphite Products Corp | 2, 3-bis-(oxybenzyl)-butane derivatives |
| US3769350A (en) * | 1968-12-09 | 1973-10-30 | Hoffmann La Roche | Method for making 2,3-dimethyl-1,4-bis(3,4 - hydrocarbonyloxyphenyl) - 1,4-butanedione |
| US3906004A (en) * | 1968-12-09 | 1975-09-16 | Hoffmann La Roche | Stereoselective synthesis of intermediate for preparation of meso-nordihydroguaiaretic acid |
| US3843728A (en) * | 1968-12-09 | 1974-10-22 | Hoffmann La Roche | Racemic-diketone compounds |
-
1982
- 1982-10-25 US US06/436,444 patent/US4562298A/en not_active Expired - Lifetime
-
1985
- 1985-11-04 AU AU51958/86A patent/AU5195886A/en not_active Abandoned
- 1985-11-04 WO PCT/US1985/002164 patent/WO1987002661A1/en active IP Right Grant
- 1985-11-04 EP EP85905968A patent/EP0247035B1/en not_active Expired - Lifetime
- 1985-11-04 AT AT85905968T patent/ATE49745T1/de not_active IP Right Cessation
- 1985-11-04 DE DE8585905968T patent/DE3575552D1/de not_active Expired - Lifetime
- 1985-11-04 JP JP60505283A patent/JPS63501564A/ja active Granted
-
1987
- 1987-07-01 DK DK338887A patent/DK338887A/da not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011190267A (ja) * | 2005-01-05 | 2011-09-29 | National Defense Education & Research Foundation | ウリジン２リン酸（ｕｄｐ）−グルクロン酸転移酵素２ｂ（ｕｇｔ２ｂ）の抑制剤及び促進剤 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0247035B1 (en) | 1990-01-24 |
| DE3575552D1 (de) | 1990-03-01 |
| JPH034530B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1991-01-23 |
| ATE49745T1 (de) | 1990-02-15 |
| DK338887A (da) | 1987-07-29 |
| US4562298A (en) | 1985-12-31 |
| EP0247035A1 (en) | 1987-12-02 |
| WO1987002661A1 (en) | 1987-05-07 |
| DK338887D0 (da) | 1987-07-01 |
| AU5195886A (en) | 1987-05-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Zulfiqar et al. | One-pot aza-Diels–Alder reactions in ionic liquids | |
| FR2586683A1 (fr) | Nouveaux derives de neothramycine, leur procede de preparation et leur application en tant que medicaments | |
| FR2642069A1 (fr) | Nouveaux derives du benzopyranne, leur preparation et les compositions pharmaceutiques qui les contiennent | |
| FR2963006A1 (fr) | Procede de preparation de derives de nitro-benzofurane | |
| HU194858B (en) | Process for producing dibenzo/b,d/pirane derivatives and pharmaceutical compositions containing them | |
| JPS5946233B2 (ja) | クロマン誘導体の製造方法 | |
| HU179972B (en) | Process for preparing tetrahydro-benzoxocine- and cys-hexahydro-dibenzo-pyranone derivatives | |
| EP0096480B1 (en) | Preparation of 6a, 10a-trans-hexahydrodibenzopyranones | |
| FR2657081A1 (fr) | Nouveaux derives d'arylvinylamide, leur procede de fabrication et leur application en therapeutique. | |
| JPS63501564A (ja) | ラセミ・ノルジヒドログアヤレチン酸および中間体 | |
| JPS61129145A (ja) | ヒドロキノン誘導体及びその製造方法 | |
| BE900835R (fr) | Derives de phenethanol-amine. | |
| US4954659A (en) | 1,4-bis (dihydroxyphenyl) butane and analogs | |
| KR20080046729A (ko) | 산소 함유 트라이- 또는 테트라-사이클릭 터페노이드화합물 | |
| JPH0466218B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| AU654937B2 (en) | Racemic nordihydroguaiaretic acid and intermediates | |
| EP0002408A1 (fr) | Nouveaux composés phénoxy-alcanols substitués, leur procédé de préparation et leur application en thérapeutique | |
| EP0685473B1 (fr) | Composés benzohétérocycliques, en tant qu'antioxydants | |
| Lutz et al. | The Configurations of the Alkoxy-1, 2-Dibenzoyl-Ethylenes and Related Compounds | |
| Viallon et al. | Thermal and acid-catalysed sigmatropic rearrangements of allylamino-methoxy-1, 2-benzoquinones | |
| CH629741A5 (fr) | Arylenedioxy-bis-dicetones, leur preparation et leur utilisation comme medicaments. | |
| KR100783626B1 (ko) | 항산화 활성을 갖는 ｎｄｇａ 및 그 유도체 합성법 | |
| JPH0466219B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | ||
| JPS5989638A (ja) | アリ−ルオキシアルキル化合物の製造法 | |
| Křepelka et al. | Some derivatives of 4-aryl-2, 3-dicyano-1-naphthol |