JP2001294549A - レゾルシノール誘導体の製造方法 - Google Patents
レゾルシノール誘導体の製造方法Info
- Publication number
- JP2001294549A JP2001294549A JP2001071785A JP2001071785A JP2001294549A JP 2001294549 A JP2001294549 A JP 2001294549A JP 2001071785 A JP2001071785 A JP 2001071785A JP 2001071785 A JP2001071785 A JP 2001071785A JP 2001294549 A JP2001294549 A JP 2001294549A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- formula
- aryl
- compound
- acyl
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 10
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 title abstract description 15
- 150000001875 compounds Chemical class 0.000 claims abstract description 324
- 125000006239 protecting group Chemical group 0.000 claims abstract description 65
- -1 4-substituted resorcinol Chemical class 0.000 claims abstract description 43
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 169
- 125000003118 aryl group Chemical group 0.000 claims description 159
- 229910052739 hydrogen Inorganic materials 0.000 claims description 71
- 239000001257 hydrogen Substances 0.000 claims description 71
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 56
- 125000005843 halogen group Chemical group 0.000 claims description 54
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 52
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 49
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 47
- 125000003545 alkoxy group Chemical group 0.000 claims description 46
- 125000000304 alkynyl group Chemical group 0.000 claims description 45
- 125000003342 alkenyl group Chemical group 0.000 claims description 42
- 125000002252 acyl group Chemical group 0.000 claims description 37
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 19
- 125000003282 alkyl amino group Chemical group 0.000 claims description 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
- 125000004442 acylamino group Chemical group 0.000 claims description 16
- 125000004423 acyloxy group Chemical group 0.000 claims description 16
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical group BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 125000006564 (C4-C8) cycloalkyl group Chemical group 0.000 claims description 11
- 230000002140 halogenating effect Effects 0.000 claims description 11
- 125000001246 bromo group Chemical group Br* 0.000 claims description 10
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 239000011630 iodine Chemical group 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 150000001721 carbon Chemical group 0.000 claims description 5
- 229910052801 chlorine Chemical group 0.000 claims description 5
- 239000000460 chlorine Chemical group 0.000 claims description 5
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 5
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 5
- 241001553014 Myrsine salicina Species 0.000 claims 8
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 8
- 235000014676 Phragmites communis Nutrition 0.000 claims 5
- 238000010276 construction Methods 0.000 claims 1
- 229920001577 copolymer Chemical group 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract description 18
- 239000002904 solvent Substances 0.000 abstract description 16
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 abstract description 6
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 abstract description 5
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract description 4
- 239000002841 Lewis acid Substances 0.000 abstract description 3
- 150000007517 lewis acids Chemical class 0.000 abstract description 3
- 229910015900 BF3 Inorganic materials 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 210000003491 skin Anatomy 0.000 description 20
- 239000000243 solution Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 238000003556 assay Methods 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 239000007787 solid Substances 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
- 102000003425 Tyrosinase Human genes 0.000 description 5
- 108060008724 Tyrosinase Proteins 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 238000006482 condensation reaction Methods 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 5
- 238000010561 standard procedure Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 206010040829 Skin discolouration Diseases 0.000 description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000007854 depigmenting agent Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 3
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 description 3
- 102000000589 Interleukin-1 Human genes 0.000 description 3
- 108010002352 Interleukin-1 Proteins 0.000 description 3
- 229920000877 Melamine resin Polymers 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 235000019445 benzyl alcohol Nutrition 0.000 description 3
- 238000004061 bleaching Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000000499 gel Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 3
- 210000002752 melanocyte Anatomy 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- WHNFPRLDDSXQCL-UAZQEYIDSA-N α-msh Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(N)=O)NC(=O)[C@H](CO)NC(C)=O)C1=CC=C(O)C=C1 WHNFPRLDDSXQCL-UAZQEYIDSA-N 0.000 description 3
- NAVXWBOUFIPGCV-UHFFFAOYSA-N 2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-5-phenylmethoxyphenol Chemical compound C=1C=C(C=2CCC3(CC=2)OCCO3)C(O)=CC=1OCC1=CC=CC=C1 NAVXWBOUFIPGCV-UHFFFAOYSA-N 0.000 description 2
- IUAKULWBKVANKM-UHFFFAOYSA-N 4-(1,4-dioxaspiro[4.5]decan-8-yl)benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1CCC2(OCCO2)CC1 IUAKULWBKVANKM-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 description 2
- 102400000740 Melanocyte-stimulating hormone alpha Human genes 0.000 description 2
- 101710200814 Melanotropin alpha Proteins 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- CGXAANJNKIYLCE-MGCOHNPYSA-N OC(=O)C[C@H]1CC[C@@H](CC1)c1ccc(O)cc1O Chemical compound OC(=O)C[C@H]1CC[C@@H](CC1)c1ccc(O)cc1O CGXAANJNKIYLCE-MGCOHNPYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 2
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 238000009825 accumulation Methods 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 239000013592 cell lysate Substances 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000006210 lotion Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000004502 1,2,3-oxadiazolyl group Chemical group 0.000 description 1
- 125000004511 1,2,3-thiadiazolyl group Chemical group 0.000 description 1
- 125000004529 1,2,3-triazinyl group Chemical group N1=NN=C(C=C1)* 0.000 description 1
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 description 1
- 125000004514 1,2,4-thiadiazolyl group Chemical group 0.000 description 1
- 125000004530 1,2,4-triazinyl group Chemical group N1=NC(=NC=C1)* 0.000 description 1
- 125000003363 1,3,5-triazinyl group Chemical group N1=C(N=CN=C1)* 0.000 description 1
- VKRKCBWIVLSRBJ-UHFFFAOYSA-N 1,4-dioxaspiro[4.5]decan-8-one Chemical compound C1CC(=O)CCC21OCCO2 VKRKCBWIVLSRBJ-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- GRNDCTQCECXRLK-UHFFFAOYSA-N 2-cyclopentylbenzene-1,3-diol Chemical compound OC1=CC=CC(O)=C1C1CCCC1 GRNDCTQCECXRLK-UHFFFAOYSA-N 0.000 description 1
- KOZUBROKGRNNGP-UHFFFAOYSA-N 2-phenylmethoxycyclohex-2-en-1-one Chemical compound O=C1CCCC=C1OCC1=CC=CC=C1 KOZUBROKGRNNGP-UHFFFAOYSA-N 0.000 description 1
- CHUFWVWPXCKZKO-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)-n-ethylcyclohexane-1-carboxamide Chemical compound C1C(C(=O)NCC)CCCC1C1=CC=C(O)C=C1O CHUFWVWPXCKZKO-UHFFFAOYSA-N 0.000 description 1
- MPSUHRWTECGDSD-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)-n-hydroxycyclohexane-1-carboxamide Chemical compound C1C(C(=O)NO)CCCC1C1=CC=C(O)C=C1O MPSUHRWTECGDSD-UHFFFAOYSA-N 0.000 description 1
- VUOGVPXXBCFSLV-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)cyclohex-2-en-1-one Chemical compound OC1=CC(O)=CC=C1C1=CC(=O)CCC1 VUOGVPXXBCFSLV-UHFFFAOYSA-N 0.000 description 1
- HJIQNULRLPDBIJ-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)cyclohexan-1-one Chemical compound OC1=CC(O)=CC=C1C1CC(=O)CCC1 HJIQNULRLPDBIJ-UHFFFAOYSA-N 0.000 description 1
- UTZJPHCFUKFPGI-UHFFFAOYSA-N 3-(2,4-dihydroxyphenyl)cyclopentan-1-one Chemical compound OC1=CC(O)=CC=C1C1CC(=O)CC1 UTZJPHCFUKFPGI-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical class C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
- FDZSSAFDXALWAG-UHFFFAOYSA-N 4-(2,4-dihydroxyphenyl)cyclohex-3-en-1-one Chemical compound OC1=CC(O)=CC=C1C1=CCC(=O)CC1 FDZSSAFDXALWAG-UHFFFAOYSA-N 0.000 description 1
- OFMGTSMXUQYLMA-UHFFFAOYSA-N 4-(2,4-dihydroxyphenyl)cyclohexan-1-one Chemical compound OC1=CC(O)=CC=C1C1CCC(=O)CC1 OFMGTSMXUQYLMA-UHFFFAOYSA-N 0.000 description 1
- OOGMKYWSHKZVFR-UHFFFAOYSA-N 4-(3,3-difluorocyclohexyl)benzene-1,3-diol Chemical compound OC1=CC(O)=CC=C1C1CC(F)(F)CCC1 OOGMKYWSHKZVFR-UHFFFAOYSA-N 0.000 description 1
- DWICTFHZZVZTOI-UHFFFAOYSA-N 4-(3-hydroxy-3-methylcyclohexyl)benzene-1,3-diol Chemical compound C1C(C)(O)CCCC1C1=CC=C(O)C=C1O DWICTFHZZVZTOI-UHFFFAOYSA-N 0.000 description 1
- LTHQUKLTINLAMQ-UHFFFAOYSA-N 4-(3-hydroxyiminocyclohexen-1-yl)benzene-1,3-diol Chemical compound ON=C1CCCC(C=2C(=CC(O)=CC=2)O)=C1 LTHQUKLTINLAMQ-UHFFFAOYSA-N 0.000 description 1
- RVECCVXTBHLMOC-UHFFFAOYSA-N 4-(3-hydroxyiminocyclohexyl)-3-methoxyphenol Chemical compound COC1=CC(O)=CC=C1C1CC(=NO)CCC1 RVECCVXTBHLMOC-UHFFFAOYSA-N 0.000 description 1
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- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation
- C07C37/07—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by conversion of non-aromatic six-membered rings or of such rings formed in situ into aromatic six-membered rings, e.g. by dehydrogenation with simultaneous reduction of C=O group in that ring
-
- 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
- C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
- C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
- C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
-
- 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
- C07C45/68—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 increase in the number of carbon atoms
- C07C45/70—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 increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—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 increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
- C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
- C07C49/747—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/18—Systems containing only non-condensed rings with a ring being at least seven-membered
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S977/00—Nanotechnology
- Y10S977/902—Specified use of nanostructure
- Y10S977/904—Specified use of nanostructure for medical, immunological, body treatment, or diagnosis
- Y10S977/926—Topical chemical, e.g. cosmetic or sunscreen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18970400P | 2000-03-15 | 2000-03-15 | |
| US60/189704 | 2000-03-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2001294549A true JP2001294549A (ja) | 2001-10-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001071785A Pending JP2001294549A (ja) | 2000-03-15 | 2001-03-14 | レゾルシノール誘導体の製造方法 |
Country Status (18)
| Country | Link |
|---|---|
| US (3) | US6504037B2 (enExample) |
| EP (1) | EP1134207A1 (enExample) |
| JP (1) | JP2001294549A (enExample) |
| KR (1) | KR100432303B1 (enExample) |
| CN (1) | CN1325838A (enExample) |
| AR (1) | AR030055A1 (enExample) |
| AU (1) | AU782397B2 (enExample) |
| BR (1) | BR0100982A (enExample) |
| CA (1) | CA2340486A1 (enExample) |
| CZ (1) | CZ2001930A3 (enExample) |
| HK (1) | HK1040987A1 (enExample) |
| ID (1) | ID29673A (enExample) |
| IL (1) | IL141915A0 (enExample) |
| IN (1) | IN192530B (enExample) |
| PL (1) | PL346463A1 (enExample) |
| RU (1) | RU2213087C2 (enExample) |
| YU (1) | YU18601A (enExample) |
| ZA (1) | ZA200102070B (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7135318B2 (en) | 2002-07-02 | 2006-11-14 | Sumitomo Chemical Company, Limited | Modified reductase and its gene |
| US7163814B2 (en) | 2002-07-03 | 2007-01-16 | Sumitomo Chemical Company, Limited | Modified reductase and its gene, and use thereof |
| JP2007523932A (ja) * | 2004-02-27 | 2007-08-23 | ユニリーバー・ナームローゼ・ベンノートシヤープ | 皮膚美白剤、組成物及び方法 |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6828460B2 (en) * | 1999-03-22 | 2004-12-07 | Pfizer Inc. | Resorcinol derivatives |
| US6863897B2 (en) * | 2002-03-22 | 2005-03-08 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Stabilization of resorcinol derivatives in cosmetic compositions |
| US6852310B2 (en) | 2002-08-23 | 2005-02-08 | Unilever Home & Personal Care Usa Division Of Conopco, Inc. | Skin lightening agents, compositions and methods |
| CN100383573C (zh) * | 2002-12-02 | 2008-04-23 | 3M创新有限公司 | 多光源照明系统 |
| US6875425B2 (en) | 2002-12-12 | 2005-04-05 | Unilever Home & Personal Care Usa | Skin lightening agents, compositions and methods |
| US7524485B2 (en) | 2002-12-12 | 2009-04-28 | Unilever Home & Personal Care, Usa, Division Of Conopco, Inc. | Skin lightening agents, compositions and methods |
| US7338979B2 (en) | 2003-02-11 | 2008-03-04 | Warner-Lambert Company | Depigmentation agents |
| US20060062865A1 (en) * | 2004-09-17 | 2006-03-23 | Nebojsa Ilic | Tyrosinase inhibitor and method for preparation |
| US20060210497A1 (en) * | 2005-03-18 | 2006-09-21 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Novel resorcinol derivatives |
| US20060210498A1 (en) * | 2005-03-18 | 2006-09-21 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Novel resorcinol derivatives for skin |
| US7250158B1 (en) | 2006-03-30 | 2007-07-31 | Conopco, Inc. | Skin lightening agents, compositions and methods |
| US7247294B1 (en) | 2006-03-30 | 2007-07-24 | Conopco, Inc. | Skin lightening agents, compositions and methods |
| US7270805B1 (en) | 2006-03-30 | 2007-09-18 | Conopco, Inc. | Skin lightening agents, compositions and methods |
| EP2964182B1 (en) | 2013-03-08 | 2018-02-14 | Unilever PLC, a company registered in England and Wales under company no. 41424 of | Resorcinol compounds for dermatological use |
| WO2017215863A1 (en) | 2016-06-15 | 2017-12-21 | Unilever N.V. | Method and cosmetic composition for enhanced transdermal delivery of alkyl substituted resorcinol |
| CN111909012B (zh) * | 2020-08-24 | 2022-10-21 | 浙江工业大学台州研究院 | 一种高选择性、高转化制备1,3-环己二酮的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0651619B2 (ja) * | 1988-05-09 | 1994-07-06 | 株式会社クラレ | 美白剤 |
| US5059438A (en) * | 1990-02-05 | 1991-10-22 | Enzytech, Inc. | Compositions and methods for inhibiting browning in foods using resorcinol derivatives |
| FR2704753B1 (fr) * | 1993-05-06 | 1995-06-30 | Oreal | Utilisation de derives de la 4-thio resorcine ou 4-thio 1-3-dihydroxybenzene, dans des compositions cosmetiques ou dermopharmaceutiques a action depigmentante. |
| FR2714601B1 (fr) * | 1993-12-30 | 1996-02-09 | Oreal | Composition dépigmentante pour le traitement simultané des couches superficielles et profondes, son utilisation. |
| BR9803596A (pt) * | 1997-09-23 | 2000-04-25 | Pfizer Prod Inc | Derivados do resorcinol. |
| PA8469601A1 (es) * | 1998-04-10 | 2000-09-29 | Pfizer Prod Inc | Procedimiento para alquilar sulfonamidas impedidas estericamente |
| SI1165495T1 (en) * | 1999-03-22 | 2005-08-31 | Pfizer | Resorcinol derivatives |
-
2001
- 2001-03-05 EP EP01301995A patent/EP1134207A1/en not_active Withdrawn
- 2001-03-08 US US09/801,999 patent/US6504037B2/en not_active Expired - Fee Related
- 2001-03-08 IL IL14191501A patent/IL141915A0/xx unknown
- 2001-03-09 YU YU18601A patent/YU18601A/sh unknown
- 2001-03-12 AU AU26477/01A patent/AU782397B2/en not_active Ceased
- 2001-03-12 IN IN287DE2001 patent/IN192530B/en unknown
- 2001-03-13 AR ARP010101165A patent/AR030055A1/es unknown
- 2001-03-13 CA CA002340486A patent/CA2340486A1/en not_active Abandoned
- 2001-03-13 ZA ZA200102070A patent/ZA200102070B/xx unknown
- 2001-03-14 ID IDP20010223D patent/ID29673A/id unknown
- 2001-03-14 RU RU2001106948/04A patent/RU2213087C2/ru not_active IP Right Cessation
- 2001-03-14 CZ CZ2001930A patent/CZ2001930A3/cs unknown
- 2001-03-14 BR BR0100982-6A patent/BR0100982A/pt not_active IP Right Cessation
- 2001-03-14 JP JP2001071785A patent/JP2001294549A/ja active Pending
- 2001-03-14 KR KR10-2001-0013250A patent/KR100432303B1/ko not_active Expired - Fee Related
- 2001-03-15 CN CN01119693A patent/CN1325838A/zh active Pending
- 2001-03-15 PL PL01346463A patent/PL346463A1/xx unknown
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2002
- 2002-04-11 HK HK02102738.1A patent/HK1040987A1/zh unknown
- 2002-10-28 US US10/282,201 patent/US6861564B2/en not_active Expired - Fee Related
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2005
- 2005-01-14 US US11/036,262 patent/US20050143594A1/en not_active Abandoned
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7135318B2 (en) | 2002-07-02 | 2006-11-14 | Sumitomo Chemical Company, Limited | Modified reductase and its gene |
| US7163814B2 (en) | 2002-07-03 | 2007-01-16 | Sumitomo Chemical Company, Limited | Modified reductase and its gene, and use thereof |
| JP2007523932A (ja) * | 2004-02-27 | 2007-08-23 | ユニリーバー・ナームローゼ・ベンノートシヤープ | 皮膚美白剤、組成物及び方法 |
| JP4855382B2 (ja) * | 2004-02-27 | 2012-01-18 | ユニリーバー・ナームローゼ・ベンノートシヤープ | 皮膚美白剤、組成物及び方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2647701A (en) | 2001-09-20 |
| AU782397B2 (en) | 2005-07-21 |
| IN192530B (enExample) | 2004-04-24 |
| US20050143594A1 (en) | 2005-06-30 |
| ID29673A (id) | 2001-09-20 |
| US6861564B2 (en) | 2005-03-01 |
| US20030088113A1 (en) | 2003-05-08 |
| CA2340486A1 (en) | 2001-09-15 |
| BR0100982A (pt) | 2001-12-04 |
| KR20010096608A (ko) | 2001-11-07 |
| US6504037B2 (en) | 2003-01-07 |
| IL141915A0 (en) | 2002-03-10 |
| AR030055A1 (es) | 2003-08-13 |
| KR100432303B1 (ko) | 2004-05-20 |
| YU18601A (sh) | 2003-07-07 |
| RU2213087C2 (ru) | 2003-09-27 |
| HK1040987A1 (zh) | 2002-06-28 |
| US20020032352A1 (en) | 2002-03-14 |
| PL346463A1 (en) | 2001-09-24 |
| CN1325838A (zh) | 2001-12-12 |
| EP1134207A1 (en) | 2001-09-19 |
| CZ2001930A3 (cs) | 2001-10-17 |
| ZA200102070B (en) | 2002-09-13 |
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