PL89681B1 - - Google Patents
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- Publication number
- PL89681B1 PL89681B1 PL1972159046A PL15904672A PL89681B1 PL 89681 B1 PL89681 B1 PL 89681B1 PL 1972159046 A PL1972159046 A PL 1972159046A PL 15904672 A PL15904672 A PL 15904672A PL 89681 B1 PL89681 B1 PL 89681B1
- Authority
- PL
- Poland
- Prior art keywords
- group
- substituted
- benzoyl
- anthracene
- preparation
- Prior art date
Links
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 46
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 33
- 238000002360 preparation method Methods 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- -1 benzoyl halide Chemical class 0.000 claims description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 26
- YUTJCNNFTOIOGT-UHFFFAOYSA-N anthracene-1,8,9-triol Chemical compound C1=CC(O)=C2C(O)=C3C(O)=CC=CC3=CC2=C1 YUTJCNNFTOIOGT-UHFFFAOYSA-N 0.000 claims description 22
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 12
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000011261 inert gas Substances 0.000 claims description 8
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 7
- 239000008096 xylene Substances 0.000 claims description 7
- 125000005157 alkyl carboxy group Chemical group 0.000 claims description 6
- 150000001454 anthracenes Chemical class 0.000 claims description 6
- 239000012298 atmosphere Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 6
- 229940011051 isopropyl acetate Drugs 0.000 claims description 6
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004104 aryloxy group Chemical group 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical group ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 claims description 4
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 239000003849 aromatic solvent Substances 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000000758 substrate Substances 0.000 claims 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
- 150000002148 esters Chemical class 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 23
- 239000000047 product Substances 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 15
- 238000009835 boiling Methods 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- 238000000354 decomposition reaction Methods 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 229960002311 dithranol Drugs 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- NUZWLKWWNNJHPT-UHFFFAOYSA-N anthralin Chemical compound C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O NUZWLKWWNNJHPT-UHFFFAOYSA-N 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- ZZBWSNKBZKPGAK-UHFFFAOYSA-N chrysophanol-9-anthrone Chemical compound C1=CC=C2CC3=CC(C)=CC(O)=C3C(=O)C2=C1O ZZBWSNKBZKPGAK-UHFFFAOYSA-N 0.000 description 7
- 239000006072 paste Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000000825 pharmaceutical preparation Substances 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- DSGKWFGEUBCEIE-UHFFFAOYSA-N (2-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C(Cl)=O DSGKWFGEUBCEIE-UHFFFAOYSA-N 0.000 description 5
- 239000006071 cream Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 5
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- 239000011269 tar Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- DVIHKVWYFXLBEM-UHFFFAOYSA-N 2-hydroxybenzoyl chloride Chemical compound OC1=CC=CC=C1C(Cl)=O DVIHKVWYFXLBEM-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- FLYYNAHKLCJUNM-UHFFFAOYSA-N [8,9-bis[(2-hydroxybenzoyl)oxy]anthracen-1-yl] 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC2=CC3=CC=CC(OC(=O)C=4C(=CC=CC=4)O)=C3C(OC(=O)C=3C(=CC=CC=3)O)=C12 FLYYNAHKLCJUNM-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000005690 diesters Chemical class 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JBGKVNQFVAJOGC-UHFFFAOYSA-N 3-methylanthracene-1,8,9-triol Chemical compound OC1=CC=CC2=CC3=CC(C)=CC(O)=C3C(O)=C21 JBGKVNQFVAJOGC-UHFFFAOYSA-N 0.000 description 2
- CFKMVGJGLGKFKI-UHFFFAOYSA-N 4-chloro-m-cresol Chemical compound CC1=CC(O)=CC=C1Cl CFKMVGJGLGKFKI-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- DOXWIHJDTLQCNC-UHFFFAOYSA-N [8,9-bis[(2-acetyloxybenzoyl)oxy]anthracen-1-yl] 2-acetyloxybenzoate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)OC1=CC=CC2=CC3=CC=CC(OC(=O)C=4C(=CC=CC=4)OC(C)=O)=C3C(OC(=O)C=3C(=CC=CC=3)OC(C)=O)=C12 DOXWIHJDTLQCNC-UHFFFAOYSA-N 0.000 description 2
- WNMGJQATFDJVPY-UHFFFAOYSA-N [8,9-bis[(4-chlorobenzoyl)oxy]anthracen-1-yl] 4-chlorobenzoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OC1=CC=CC2=CC3=CC=CC(OC(=O)C=4C=CC(Cl)=CC=4)=C3C(OC(=O)C=3C=CC(Cl)=CC=3)=C12 WNMGJQATFDJVPY-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 2
- 150000001793 charged compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- HBGGXOJOCNVPFY-UHFFFAOYSA-N diisononyl phthalate Chemical compound CC(C)CCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCC(C)C HBGGXOJOCNVPFY-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000004452 microanalysis Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000010802 sludge Substances 0.000 description 2
- 239000002002 slurry Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 150000005691 triesters Chemical class 0.000 description 2
- MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 1
- LSVICRMDTZSTDC-UHFFFAOYSA-N 2-acetyloxybenzoic acid Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CC(=O)OC1=CC=CC=C1C(O)=O LSVICRMDTZSTDC-UHFFFAOYSA-N 0.000 description 1
- NXTNASSYJUXJDV-UHFFFAOYSA-N 3-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1 NXTNASSYJUXJDV-UHFFFAOYSA-N 0.000 description 1
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 1
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 1
- 229940090248 4-hydroxybenzoic acid Drugs 0.000 description 1
- YIPHYCQSJTXLFM-UHFFFAOYSA-N 4-hydroxybenzoyl chloride Chemical compound OC1=CC=C(C(Cl)=O)C=C1 YIPHYCQSJTXLFM-UHFFFAOYSA-N 0.000 description 1
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 229940124091 Keratolytic Drugs 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 206010040880 Skin irritation Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- UAYFYAXIQROSAY-UHFFFAOYSA-N [2-(dichloromethyl)phenyl] acetate Chemical compound CC(=O)OC1=CC=CC=C1C(Cl)Cl UAYFYAXIQROSAY-UHFFFAOYSA-N 0.000 description 1
- SJTJIHSASLJKQJ-UHFFFAOYSA-N [8,9-bis[(2-chlorobenzoyl)oxy]anthracen-1-yl] 2-chlorobenzoate Chemical compound ClC1=CC=CC=C1C(=O)OC1=CC=CC2=CC3=CC=CC(OC(=O)C=4C(=CC=CC=4)Cl)=C3C(OC(=O)C=3C(=CC=CC=3)Cl)=C12 SJTJIHSASLJKQJ-UHFFFAOYSA-N 0.000 description 1
- MBJDIOVEOFJXCX-UHFFFAOYSA-N [8,9-bis[(2-methoxybenzoyl)oxy]anthracen-1-yl] 2-methoxybenzoate Chemical compound COC1=C(C(=O)OC2=CC=CC3=CC4=CC=CC(=C4C(=C23)OC(C2=C(C=CC=C2)OC)=O)OC(C2=C(C=CC=C2)OC)=O)C=CC=C1 MBJDIOVEOFJXCX-UHFFFAOYSA-N 0.000 description 1
- FPBILGFSEZTWSF-UHFFFAOYSA-N [8,9-bis[(3-methylbenzoyl)oxy]anthracen-1-yl] 3-methylbenzoate Chemical compound CC1=CC=CC(C(=O)OC=2C3=C(OC(=O)C=4C=C(C)C=CC=4)C4=C(OC(=O)C=5C=C(C)C=CC=5)C=CC=C4C=C3C=CC=2)=C1 FPBILGFSEZTWSF-UHFFFAOYSA-N 0.000 description 1
- BEZJHGSUMSALKN-UHFFFAOYSA-N [8,9-bis[(4-hydroxybenzoyl)oxy]anthracen-1-yl] 4-hydroxybenzoate Chemical compound C1=CC(O)=CC=C1C(=O)OC1=CC=CC2=CC3=CC=CC(OC(=O)C=4C=CC(O)=CC=4)=C3C(OC(=O)C=3C=CC(O)=CC=3)=C12 BEZJHGSUMSALKN-UHFFFAOYSA-N 0.000 description 1
- IZDVGJPGSUXYDM-UHFFFAOYSA-N [8,9-bis[(4-methoxybenzoyl)oxy]anthracen-1-yl] 4-methoxybenzoate Chemical compound C1=CC(OC)=CC=C1C(=O)OC1=CC=CC2=CC3=CC=CC(OC(=O)C=4C=CC(OC)=CC=4)=C3C(OC(=O)C=3C=CC(OC)=CC=3)=C12 IZDVGJPGSUXYDM-UHFFFAOYSA-N 0.000 description 1
- PZCMQRPAWKKQSI-UHFFFAOYSA-N [8,9-bis[(4-methylbenzoyl)oxy]anthracen-1-yl] 4-methylbenzoate Chemical compound C1=CC(C)=CC=C1C(=O)OC1=CC=CC2=CC3=CC=CC(OC(=O)C=4C=CC(C)=CC=4)=C3C(OC(=O)C=3C=CC(C)=CC=3)=C12 PZCMQRPAWKKQSI-UHFFFAOYSA-N 0.000 description 1
- RZNMFQPUXCSJSB-UHFFFAOYSA-N [8,9-bis[(4-nitrobenzoyl)oxy]anthracen-1-yl] 4-nitrobenzoate Chemical compound C1=CC([N+](=O)[O-])=CC=C1C(=O)OC1=CC=CC2=CC3=CC=CC(OC(=O)C=4C=CC(=CC=4)[N+]([O-])=O)=C3C(OC(=O)C=3C=CC(=CC=3)[N+]([O-])=O)=C12 RZNMFQPUXCSJSB-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
- CSYSXVZYJUSHOB-UHFFFAOYSA-N anthracen-1-yl 2-hydroxybenzoate Chemical compound Oc1ccccc1C(=O)Oc1cccc2cc3ccccc3cc12 CSYSXVZYJUSHOB-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000005829 chemical entities Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 229960002242 chlorocresol Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000003246 corticosteroid Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229960000890 hydrocortisone Drugs 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001530 keratinolytic effect Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- PUPKPAZSFZOLOR-UHFFFAOYSA-N n,n-dimethylformamide;toluene Chemical compound CN(C)C=O.CC1=CC=CC=C1 PUPKPAZSFZOLOR-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 230000036556 skin irritation Effects 0.000 description 1
- 231100000475 skin irritation Toxicity 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/78—Benzoic acid esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/88—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with esterified carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
- C07C69/84—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring
- C07C69/92—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring of monocyclic hydroxy carboxylic acids, the hydroxy groups and the carboxyl groups of which are bound to carbon atoms of a six-membered aromatic ring with etherified hydroxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Dermatology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB5492771A GB1361879A (en) | 1971-11-26 | 1971-11-26 | Benzoyl esters of 1,8,9-trihydroxy-anthracene processes for their preparation and compositions incorporating them |
Publications (1)
Publication Number | Publication Date |
---|---|
PL89681B1 true PL89681B1 (is") | 1976-12-31 |
Family
ID=10472486
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PL1972159046A PL89681B1 (is") | 1971-11-26 | 1972-11-23 |
Country Status (14)
Country | Link |
---|---|
JP (1) | JPS5531766B2 (is") |
BE (1) | BE791643A (is") |
CA (1) | CA996134A (is") |
CH (1) | CH584181A5 (is") |
CS (1) | CS161968B2 (is") |
DK (1) | DK141116B (is") |
FI (1) | FI56371C (is") |
FR (1) | FR2161058B1 (is") |
GB (1) | GB1361879A (is") |
HU (1) | HU167374B (is") |
IE (1) | IE37193B1 (is") |
NL (1) | NL7215802A (is") |
PL (1) | PL89681B1 (is") |
SE (2) | SE400548B (is") |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2426971A1 (fr) * | 1978-05-26 | 1979-12-21 | Peugeot | Dispositif contacteur electrique associe a un levier de commande |
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 |
FR2591222B1 (fr) * | 1985-12-11 | 1988-07-22 | Cird | Mono, di et tri-esters de dihydroxy-1,8 phenyl-10 anthrone-9 ou anthranol-9, leur procede de preparation et leur utilisation en medecine humaine ou veterinaire et en cosmetique |
JP6255210B2 (ja) * | 2013-10-24 | 2017-12-27 | アーゼッド・エレクトロニック・マテリアルズ(ルクセンブルグ)ソシエテ・ア・レスポンサビリテ・リミテ | レジスト下層膜形成組成物 |
-
0
- BE BE791643D patent/BE791643A/xx not_active IP Right Cessation
-
1971
- 1971-11-26 GB GB5492771A patent/GB1361879A/en not_active Expired
-
1972
- 1972-11-22 NL NL7215802A patent/NL7215802A/xx not_active Application Discontinuation
- 1972-11-23 IE IE1633/72A patent/IE37193B1/xx unknown
- 1972-11-23 PL PL1972159046A patent/PL89681B1/pl unknown
- 1972-11-23 CS CS7976A patent/CS161968B2/cs unknown
- 1972-11-24 HU HUSE1652A patent/HU167374B/hu unknown
- 1972-11-24 FR FR7241854A patent/FR2161058B1/fr not_active Expired
- 1972-11-24 CA CA157,483A patent/CA996134A/en not_active Expired
- 1972-11-24 DK DK587672AA patent/DK141116B/da not_active IP Right Cessation
- 1972-11-24 CH CH1713572A patent/CH584181A5/xx not_active IP Right Cessation
- 1972-11-24 SE SE7215395A patent/SE400548B/xx unknown
- 1972-11-24 FI FI3329/72A patent/FI56371C/fi active
- 1972-11-27 JP JP11816272A patent/JPS5531766B2/ja not_active Expired
-
1976
- 1976-05-11 SE SE7605364A patent/SE7605364L/xx unknown
Also Published As
Publication number | Publication date |
---|---|
FR2161058B1 (is") | 1976-04-23 |
DE2257442A1 (de) | 1973-05-30 |
FI56371C (fi) | 1980-01-10 |
SE400548B (sv) | 1978-04-03 |
DK141116C (is") | 1980-06-30 |
BE791643A (fr) | 1973-03-16 |
GB1361879A (en) | 1974-07-30 |
FI56371B (fi) | 1979-09-28 |
DE2257442B2 (de) | 1977-03-10 |
CH584181A5 (is") | 1977-01-31 |
CS161968B2 (is") | 1975-06-10 |
IE37193L (en) | 1973-05-26 |
CA996134A (en) | 1976-08-31 |
FR2161058A1 (is") | 1973-07-06 |
JPS4862749A (is") | 1973-09-01 |
HU167374B (is") | 1975-09-27 |
JPS5531766B2 (is") | 1980-08-20 |
IE37193B1 (en) | 1977-05-25 |
DK141116B (da) | 1980-01-21 |
NL7215802A (is") | 1973-05-29 |
SE7605364L (sv) | 1976-05-11 |
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