FR2499556A1 - - Google Patents
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- Publication number
- FR2499556A1 FR2499556A1 FR8102572A FR8102572A FR2499556A1 FR 2499556 A1 FR2499556 A1 FR 2499556A1 FR 8102572 A FR8102572 A FR 8102572A FR 8102572 A FR8102572 A FR 8102572A FR 2499556 A1 FR2499556 A1 FR 2499556A1
- Authority
- FR
- France
- Prior art keywords
- dihydroxy
- anthrone
- ylidene
- maleate
- propionate
- 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
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- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- -1 RADICAL BENZYL Chemical class 0.000 claims abstract description 25
- 150000003254 radicals Chemical class 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 239000002537 cosmetic Substances 0.000 claims abstract description 4
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical group C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 claims description 33
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 11
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 9
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- RNERBJNDXXEXTK-SREVYHEPSA-N (z)-4-hexoxy-4-oxobut-2-enoic acid Chemical compound CCCCCCOC(=O)\C=C/C(O)=O RNERBJNDXXEXTK-SREVYHEPSA-N 0.000 claims description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 claims description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 208000002874 Acne Vulgaris Diseases 0.000 claims description 2
- 206010000496 acne Diseases 0.000 claims description 2
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 claims description 2
- 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 2
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 230000009885 systemic effect Effects 0.000 claims description 2
- KASSRDCXDIHGOK-UHFFFAOYSA-N 3h-anthracen-2-one Chemical compound C1=CC=CC2=CC3=CC(=O)CC=C3C=C21 KASSRDCXDIHGOK-UHFFFAOYSA-N 0.000 claims 5
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 claims 4
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 claims 2
- BOFGUJVLYGISIU-WAYWQWQTSA-N (z)-4-oxo-4-pentoxybut-2-enoic acid Chemical compound CCCCCOC(=O)\C=C/C(O)=O BOFGUJVLYGISIU-WAYWQWQTSA-N 0.000 claims 1
- DLRVAHCNVVWDMI-UHFFFAOYSA-N 2-butyl-1,8-dihydroxy-10h-anthracen-9-one Chemical compound C1=CC(O)=C2C(=O)C3=C(O)C(CCCC)=CC=C3CC2=C1 DLRVAHCNVVWDMI-UHFFFAOYSA-N 0.000 claims 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 claims 1
- UTOVMEACOLCUCK-PLNGDYQASA-N butyl maleate Chemical compound CCCCOC(=O)\C=C/C(O)=O UTOVMEACOLCUCK-PLNGDYQASA-N 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- DSTWFRCNXMNXTR-WAYWQWQTSA-N dipropyl (z)-but-2-enedioate Chemical compound CCCOC(=O)\C=C/C(=O)OCCC DSTWFRCNXMNXTR-WAYWQWQTSA-N 0.000 claims 1
- 125000005935 hexyloxycarbonyl group Chemical group 0.000 claims 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 2
- 101000687448 Homo sapiens REST corepressor 1 Proteins 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical group [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 1
- 102100024864 REST corepressor 1 Human genes 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 239000012071 phase Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000012298 atmosphere Substances 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 239000000741 silica gel Substances 0.000 description 9
- 229910002027 silica gel Inorganic materials 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 229960002311 dithranol Drugs 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000012300 argon atmosphere Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229940017219 methyl propionate Drugs 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- JBSLOWBPDRZSMB-FPLPWBNLSA-N dibutyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCCCC JBSLOWBPDRZSMB-FPLPWBNLSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- WZOPWGDHKKJMEA-FPLPWBNLSA-N 1-O-ethyl 4-O-pentyl (Z)-but-2-enedioate Chemical compound C(\C=C/C(=O)OCCCCC)(=O)OCC WZOPWGDHKKJMEA-FPLPWBNLSA-N 0.000 description 1
- HFZLSTDPRQSZCQ-UHFFFAOYSA-N 1-pyrrolidin-3-ylpyrrolidine Chemical compound C1CCCN1C1CNCC1 HFZLSTDPRQSZCQ-UHFFFAOYSA-N 0.000 description 1
- UHOPWFKONJYLCF-UHFFFAOYSA-N 2-(2-sulfanylethyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCS)C(=O)C2=C1 UHOPWFKONJYLCF-UHFFFAOYSA-N 0.000 description 1
- FUZLRTGGPPIBJQ-UHFFFAOYSA-N 2-n,2-n,4-n,4-n-tetramethylpyrimidine-2,4-diamine Chemical compound CN(C)C1=CC=NC(N(C)C)=N1 FUZLRTGGPPIBJQ-UHFFFAOYSA-N 0.000 description 1
- LVCGYXMMGGVONW-UHFFFAOYSA-N 3-(2,3-dihydro-1,4-benzodioxin-6-yl)-7-hydroxy-4-oxochromene-2-carboxylic acid Chemical compound O1CCOC2=CC(C=3C(=O)C4=CC=C(O)C=C4OC=3C(=O)O)=CC=C21 LVCGYXMMGGVONW-UHFFFAOYSA-N 0.000 description 1
- YPRMWCKXOZFJGF-UHFFFAOYSA-N 3-bromofuran-2,5-dione Chemical compound BrC1=CC(=O)OC1=O YPRMWCKXOZFJGF-UHFFFAOYSA-N 0.000 description 1
- LOLKAJARZKDJTD-UHFFFAOYSA-N 4-Ethoxy-4-oxobutanoic acid Chemical compound CCOC(=O)CCC(O)=O LOLKAJARZKDJTD-UHFFFAOYSA-N 0.000 description 1
- FGGPJCOTXDEUMT-SREVYHEPSA-N 4-o-butyl 1-o-ethyl (z)-but-2-enedioate Chemical compound CCCCOC(=O)\C=C/C(=O)OCC FGGPJCOTXDEUMT-SREVYHEPSA-N 0.000 description 1
- FJNCXZZQNBKEJT-UHFFFAOYSA-N 8beta-hydroxymarrubiin Natural products O1C(=O)C2(C)CCCC3(C)C2C1CC(C)(O)C3(O)CCC=1C=COC=1 FJNCXZZQNBKEJT-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 1
- 150000008425 anthrones Chemical group 0.000 description 1
- QCOAPBRVQHMEPF-UHFFFAOYSA-N bis(2-methylpropyl) butanedioate Chemical compound CC(C)COC(=O)CCC(=O)OCC(C)C QCOAPBRVQHMEPF-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- CVQRNPMXUVYAHF-UHFFFAOYSA-N cyclobutyl propanoate Chemical compound CCC(=O)OC1CCC1 CVQRNPMXUVYAHF-UHFFFAOYSA-N 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 229960002097 dibutylsuccinate Drugs 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- WIGHHCZXXMEXNW-UHFFFAOYSA-N dicyclobutyl butanedioate Chemical compound C1CCC1OC(=O)CCC(=O)OC1CCC1 WIGHHCZXXMEXNW-UHFFFAOYSA-N 0.000 description 1
- BLKQQTCUGZJWLN-QXMHVHEDSA-N dicyclohexyl (z)-but-2-enedioate Chemical compound C1CCCCC1OC(=O)\C=C/C(=O)OC1CCCCC1 BLKQQTCUGZJWLN-QXMHVHEDSA-N 0.000 description 1
- WWQSMJYMCWMODI-UHFFFAOYSA-N dicyclohexyl butanedioate Chemical compound C1CCCCC1OC(=O)CCC(=O)OC1CCCCC1 WWQSMJYMCWMODI-UHFFFAOYSA-N 0.000 description 1
- FWRFEGHSSFFLMN-UHFFFAOYSA-N dicyclopentyl butanedioate Chemical compound C1CCCC1OC(=O)CCC(=O)OC1CCCC1 FWRFEGHSSFFLMN-UHFFFAOYSA-N 0.000 description 1
- XEYHWMQDXTVNJW-UHFFFAOYSA-N dihexyl butanedioate Chemical compound CCCCCCOC(=O)CCC(=O)OCCCCCC XEYHWMQDXTVNJW-UHFFFAOYSA-N 0.000 description 1
- VHILMKFSCRWWIJ-UHFFFAOYSA-N dimethyl acetylenedicarboxylate Chemical compound COC(=O)C#CC(=O)OC VHILMKFSCRWWIJ-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- FMVJYQGSRWVMQV-UHFFFAOYSA-N ethyl propiolate Chemical compound CCOC(=O)C#C FMVJYQGSRWVMQV-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- GYZCKXAOGZSSCT-UHFFFAOYSA-N hexan-3-yl propanoate Chemical compound CCCC(CC)OC(=O)CC GYZCKXAOGZSSCT-UHFFFAOYSA-N 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000000750 progressive effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 210000004761 scalp Anatomy 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000001149 thermolysis Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
- Cosmetics (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8102572A FR2499556B1 (en, 2012) | 1981-02-10 | 1981-02-10 | |
| US06/346,893 US4464301A (en) | 1981-02-10 | 1982-02-08 | 1,8-Dihydroxy-9-anthrones derivatives substituted in the 10-position by an unsaturated radical and their use in human and veterinary medicine |
| JP57018295A JPS57149249A (en) | 1981-02-10 | 1982-02-09 | 1,8-dihydroxy-9-anthrone derivative and medicinal, veterinary and cosmetic composition containing same |
| NL8200489A NL8200489A (nl) | 1981-02-10 | 1982-02-09 | Op de 10-plaats met een onverzadigde groep gesubstitueerde derivaten van de 1,8-dihydroxy-9-anthronreeks, alsmede de toepassing ervan in farmaceutische preparaten voor mens of dier en in cosmetische preparaten. |
| IT19539/82A IT1157920B (it) | 1981-02-10 | 1982-02-09 | Derivati della serie dei diidrossi-1,8 antroni-9 sostituiti in posizione 10 con un radicale non saturo e loro impiego in medicina umana o in medicina veterinaria e in cosmetica |
| BE0/207268A BE892076A (fr) | 1981-02-10 | 1982-02-09 | Nouveaux derives de la serie des dihydroxy-1,8 anthrones-9 substituees en position 10 et leur utilisation en medecine et en cosmetique |
| CH825/82A CH651290A5 (fr) | 1981-02-10 | 1982-02-09 | Derives de la serie des dihydroxy-1,8 anthrones-9 substituees en position 10 par un radical insature. |
| SE8200745A SE437659B (sv) | 1981-02-10 | 1982-02-09 | Nya derivat av 1,8-dihydroxi-9-antron-serien, substituerade i 10-stellning med en omettad grupp och en farmaceutisk eller kosmetisk komposition derav |
| DE19823204446 DE3204446A1 (de) | 1981-02-10 | 1982-02-09 | Dihydroxyanthrone, sowie pharmazeutische und kosmetische mittel, die diese verbindungen enthalten |
| CA000395818A CA1207762A (fr) | 1981-02-10 | 1982-02-09 | Derives de la serie des dihydroxy-1,8 anthrones-9 substituees en position 10 par un radical insature et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
| GB8203673A GB2092588B (en) | 1981-02-10 | 1982-02-09 | 1-8-dihydroxy-9-anthrones substituted in the 10-position by an unsaturated radical and their use in human and veterinary medicine and in cosmetics |
| US06/615,734 US4558069A (en) | 1981-02-10 | 1984-05-31 | 1,8-Dihydroxy-9-anthrones derivatives substituted in the 10-position by an unsaturated radical used in human medicine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8102572A FR2499556B1 (en, 2012) | 1981-02-10 | 1981-02-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2499556A1 true FR2499556A1 (en, 2012) | 1982-08-13 |
| FR2499556B1 FR2499556B1 (en, 2012) | 1983-03-25 |
Family
ID=9255021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8102572A Expired FR2499556B1 (en, 2012) | 1981-02-10 | 1981-02-10 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US4464301A (en, 2012) |
| JP (1) | JPS57149249A (en, 2012) |
| BE (1) | BE892076A (en, 2012) |
| CA (1) | CA1207762A (en, 2012) |
| CH (1) | CH651290A5 (en, 2012) |
| DE (1) | DE3204446A1 (en, 2012) |
| FR (1) | FR2499556B1 (en, 2012) |
| GB (1) | GB2092588B (en, 2012) |
| IT (1) | IT1157920B (en, 2012) |
| NL (1) | NL8200489A (en, 2012) |
| SE (1) | SE437659B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4843097A (en) * | 1984-06-13 | 1989-06-27 | Groupement D'interet Economique Dit: Centre International De Recherches Dermatologiques C.I.R.D. | 10-aryl-1,8-dihydroxy-9-anthrones and their esters, process for preparing same, and use of same in human and veterinary medicine and in cosmetics |
| US5426197A (en) * | 1993-07-19 | 1995-06-20 | Teva Pharmaceutical Industries, Ltd. | 10-substituted 1,8-dihydroxy-9(10H) anthracenone pharmaceuticals |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1013901A (en) * | 1962-01-26 | 1965-12-22 | Kefalas As | Dihydroanthracene, dibenzocycloheptadiene and dibenzocycloheptatriene derivatives |
| NL299449A (en, 2012) * | 1962-10-19 | |||
| US3502697A (en) * | 1967-01-03 | 1970-03-24 | Pfizer & Co C | Antibacterial agents |
| FI57743C (fi) * | 1979-03-29 | 1980-10-10 | Orion Yhtymae Oy | Foerfarande foer framstaellning av nya 1,8-dihydroxi-10-acyl-9-antroner mot psoriasis |
| FR2492372A1 (fr) * | 1980-10-21 | 1982-04-23 | Cird | Dihydroxy-1,8 anthrones-9 substituees en position 10 et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
-
1981
- 1981-02-10 FR FR8102572A patent/FR2499556B1/fr not_active Expired
-
1982
- 1982-02-08 US US06/346,893 patent/US4464301A/en not_active Expired - Fee Related
- 1982-02-09 GB GB8203673A patent/GB2092588B/en not_active Expired
- 1982-02-09 IT IT19539/82A patent/IT1157920B/it active
- 1982-02-09 SE SE8200745A patent/SE437659B/sv not_active IP Right Cessation
- 1982-02-09 CH CH825/82A patent/CH651290A5/fr not_active IP Right Cessation
- 1982-02-09 DE DE19823204446 patent/DE3204446A1/de not_active Ceased
- 1982-02-09 JP JP57018295A patent/JPS57149249A/ja active Pending
- 1982-02-09 BE BE0/207268A patent/BE892076A/fr not_active IP Right Cessation
- 1982-02-09 NL NL8200489A patent/NL8200489A/nl not_active Application Discontinuation
- 1982-02-09 CA CA000395818A patent/CA1207762A/fr not_active Expired
Non-Patent Citations (1)
| Title |
|---|
| CA1978 * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE3204446A1 (de) | 1982-09-02 |
| NL8200489A (nl) | 1982-09-01 |
| IT8219539A0 (it) | 1982-02-09 |
| SE8200745L (sv) | 1982-08-11 |
| CH651290A5 (fr) | 1985-09-13 |
| IT1157920B (it) | 1987-02-18 |
| CA1207762A (fr) | 1986-07-15 |
| JPS57149249A (en) | 1982-09-14 |
| BE892076A (fr) | 1982-08-09 |
| FR2499556B1 (en, 2012) | 1983-03-25 |
| GB2092588A (en) | 1982-08-18 |
| GB2092588B (en) | 1984-08-22 |
| US4464301A (en) | 1984-08-07 |
| SE437659B (sv) | 1985-03-11 |
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| ER | Errata listed in the french official journal (bopi) |
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| ST | Notification of lapse |