TWI314138B - Benzoic acid ester compounds, compositions, uses and methods related thereto - Google Patents

Info

Publication number

TWI314138B

TWI314138B TW095108938A TW95108938A TWI314138B TW I314138 B TWI314138 B TW I314138B TW 095108938 A TW095108938 A TW 095108938A TW 95108938 A TW95108938 A TW 95108938A TW I314138 B TWI314138 B TW I314138B

Authority

TW

Taiwan

Prior art keywords

group

alkyl

compound

hydrogen

cycloalkyl

Prior art date

2005-03-21

Links

• Espacenet
• Global Dossier
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• 239000000203 mixture Substances 0.000 title claims description 195
• -1 Benzoic acid ester compounds Chemical class 0.000 title claims description 116
• 238000000034 method Methods 0.000 title claims description 44
• WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims description 33
• 239000005711 Benzoic acid Substances 0.000 title claims description 17
• 235000010233 benzoic acid Nutrition 0.000 title claims description 17
• 239000000516 sunscreening agent Substances 0.000 claims description 101
• 230000000475 sunscreen effect Effects 0.000 claims description 96
• 238000006243 chemical reaction Methods 0.000 claims description 60
• 150000001875 compounds Chemical class 0.000 claims description 58
• 239000001257 hydrogen Substances 0.000 claims description 49
• 229910052739 hydrogen Inorganic materials 0.000 claims description 49
• 125000000217 alkyl group Chemical group 0.000 claims description 36
• 238000009472 formulation Methods 0.000 claims description 33
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
• 239000002537 cosmetic Substances 0.000 claims description 29
• 150000002431 hydrogen Chemical class 0.000 claims description 29
• 239000000463 material Substances 0.000 claims description 28
• 239000002253 acid Substances 0.000 claims description 26
• 235000021419 vinegar Nutrition 0.000 claims description 26
• 239000003921 oil Substances 0.000 claims description 25
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 24
• 239000000047 product Substances 0.000 claims description 23
• 239000000052 vinegar Substances 0.000 claims description 23
• OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 21
• 239000008194 pharmaceutical composition Substances 0.000 claims description 19
• 238000002360 preparation method Methods 0.000 claims description 19
• 230000005855 radiation Effects 0.000 claims description 18
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
• 239000000123 paper Substances 0.000 claims description 17
• 230000004224 protection Effects 0.000 claims description 17
• 239000011347 resin Substances 0.000 claims description 17
• 229920005989 resin Polymers 0.000 claims description 17
• 150000003839 salts Chemical class 0.000 claims description 17
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 16
• 239000003795 chemical substances by application Substances 0.000 claims description 16
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 239000000460 chlorine Substances 0.000 claims description 15
• 125000000623 heterocyclic group Chemical group 0.000 claims description 15
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 14
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
• 229920000642 polymer Polymers 0.000 claims description 13
• 241001465754 Metazoa Species 0.000 claims description 12
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 12
• 239000000975 dye Substances 0.000 claims description 12
• 239000007789 gas Substances 0.000 claims description 12
• 239000006210 lotion Substances 0.000 claims description 12
• BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 239000000049 pigment Substances 0.000 claims description 12
• 239000000843 powder Substances 0.000 claims description 12
• 150000001412 amines Chemical class 0.000 claims description 11
• 238000011065 in-situ storage Methods 0.000 claims description 11
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
• 229920002125 Sokalan® Polymers 0.000 claims description 10
• 229910021386 carbon form Inorganic materials 0.000 claims description 10
• 239000006071 cream Substances 0.000 claims description 10
• 210000004209 hair Anatomy 0.000 claims description 9
• 230000006750 UV protection Effects 0.000 claims description 8
• 239000000443 aerosol Substances 0.000 claims description 8
• 239000002131 composite material Substances 0.000 claims description 8
• 239000000835 fiber Substances 0.000 claims description 8
• 239000004753 textile Substances 0.000 claims description 8
• AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 7
• AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 7
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
• 206010042496 Sunburn Diseases 0.000 claims description 7
• 125000003545 alkoxy group Chemical group 0.000 claims description 7
• 125000003277 amino group Chemical group 0.000 claims description 7
• 239000012965 benzophenone Substances 0.000 claims description 7
• 239000001913 cellulose Substances 0.000 claims description 7
• 229920002678 cellulose Polymers 0.000 claims description 7
• 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 7
• 239000003973 paint Substances 0.000 claims description 7
• 239000001993 wax Substances 0.000 claims description 7
• 229910052799 carbon Inorganic materials 0.000 claims description 6
• 238000000576 coating method Methods 0.000 claims description 6
• 239000003925 fat Substances 0.000 claims description 6
• 235000019253 formic acid Nutrition 0.000 claims description 6
• 239000000499 gel Substances 0.000 claims description 6
• BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 6
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
• 239000007921 spray Substances 0.000 claims description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 6
• 210000002268 wool Anatomy 0.000 claims description 6
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
• WVGJDUYLVYAQNT-UHFFFAOYSA-N [3-(diethylamino)phenyl] benzoate Chemical compound CCN(CC)C1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 WVGJDUYLVYAQNT-UHFFFAOYSA-N 0.000 claims description 5
• 150000001298 alcohols Chemical class 0.000 claims description 5
• 239000006185 dispersion Substances 0.000 claims description 5
• 239000003822 epoxy resin Substances 0.000 claims description 5
• 230000032050 esterification Effects 0.000 claims description 5
• 238000005886 esterification reaction Methods 0.000 claims description 5
• 150000002148 esters Chemical class 0.000 claims description 5
• 229910052751 metal Inorganic materials 0.000 claims description 5
• 239000002184 metal Substances 0.000 claims description 5
• 239000002674 ointment Substances 0.000 claims description 5
• 229920000647 polyepoxide Polymers 0.000 claims description 5
• 230000000750 progressive effect Effects 0.000 claims description 5
• 229910052707 ruthenium Inorganic materials 0.000 claims description 5
• 239000002689 soil Substances 0.000 claims description 5
• LFYCSACGUMFEPR-UHFFFAOYSA-N (3-pyrrolidin-1-ylphenyl) benzoate Chemical compound C=1C=CC=CC=1C(=O)OC(C=1)=CC=CC=1N1CCCC1 LFYCSACGUMFEPR-UHFFFAOYSA-N 0.000 claims description 4
• SDQLMXAWMGJXPR-UHFFFAOYSA-N 1-phenylethenyl 4-methoxybenzoate Chemical compound C1=CC(OC)=CC=C1C(=O)OC(=C)C1=CC=CC=C1 SDQLMXAWMGJXPR-UHFFFAOYSA-N 0.000 claims description 4
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
• KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 claims description 4
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 4
• 239000000853 adhesive Substances 0.000 claims description 4
• 230000001070 adhesive effect Effects 0.000 claims description 4
• 150000001335 aliphatic alkanes Chemical group 0.000 claims description 4
• 239000003139 biocide Substances 0.000 claims description 4
• 239000000919 ceramic Substances 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 238000004043 dyeing Methods 0.000 claims description 4
• 239000000839 emulsion Substances 0.000 claims description 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
• 239000000976 ink Substances 0.000 claims description 4
• 239000007788 liquid Substances 0.000 claims description 4
• 150000002894 organic compounds Chemical class 0.000 claims description 4
• 239000011505 plaster Substances 0.000 claims description 4
• 229920000098 polyolefin Polymers 0.000 claims description 4
• 229920002635 polyurethane Polymers 0.000 claims description 4
• 239000004814 polyurethane Substances 0.000 claims description 4
• 239000000725 suspension Substances 0.000 claims description 4
• 239000002966 varnish Substances 0.000 claims description 4
• RJQSMMZRWQXFTQ-UHFFFAOYSA-N (3-methoxyphenyl) benzoate Chemical compound COC1=CC=CC(OC(=O)C=2C=CC=CC=2)=C1 RJQSMMZRWQXFTQ-UHFFFAOYSA-N 0.000 claims description 3
• 239000004925 Acrylic resin Substances 0.000 claims description 3
• 229920000178 Acrylic resin Polymers 0.000 claims description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
• 229920000742 Cotton Polymers 0.000 claims description 3
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
• 108010010803 Gelatin Proteins 0.000 claims description 3
• 241000282412 Homo Species 0.000 claims description 3
• 239000004793 Polystyrene Substances 0.000 claims description 3
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• 239000004372 Polyvinyl alcohol Substances 0.000 claims description 3
• 238000002835 absorbance Methods 0.000 claims description 3
• RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 3
• 239000004305 biphenyl Substances 0.000 claims description 3
• 235000010290 biphenyl Nutrition 0.000 claims description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
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• 239000004202 carbamide Substances 0.000 claims description 3
• 210000000078 claw Anatomy 0.000 claims description 3
• 229920001971 elastomer Polymers 0.000 claims description 3
• 210000000720 eyelash Anatomy 0.000 claims description 3
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
• 239000011737 fluorine Substances 0.000 claims description 3
• 229910052731 fluorine Inorganic materials 0.000 claims description 3
• 239000008273 gelatin Substances 0.000 claims description 3
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• 235000019322 gelatine Nutrition 0.000 claims description 3
• 235000011852 gelatine desserts Nutrition 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims description 3
• 235000013336 milk Nutrition 0.000 claims description 3
• 210000004080 milk Anatomy 0.000 claims description 3
• 229960005181 morphine Drugs 0.000 claims description 3
• ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 3
• 229920000058 polyacrylate Polymers 0.000 claims description 3
• 229920002239 polyacrylonitrile Polymers 0.000 claims description 3
• 229920000515 polycarbonate Polymers 0.000 claims description 3
• 239000004417 polycarbonate Substances 0.000 claims description 3
• 229920000728 polyester Polymers 0.000 claims description 3
• 229920001470 polyketone Polymers 0.000 claims description 3
• 229920002223 polystyrene Polymers 0.000 claims description 3
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• 239000002243 precursor Substances 0.000 claims description 3
• 150000003254 radicals Chemical class 0.000 claims description 3
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 229940124543 ultraviolet light absorber Drugs 0.000 claims description 3
• 239000002023 wood Substances 0.000 claims description 3
• CVTGPJBFQYCRGM-UHFFFAOYSA-N (3-methoxyphenyl) hydrogen sulfate Chemical compound COC1=CC=CC(OS(O)(=O)=O)=C1 CVTGPJBFQYCRGM-UHFFFAOYSA-N 0.000 claims description 2
• KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 2
• ZUWVYBDTVBJNOX-UHFFFAOYSA-N 1-(4-tert-butylphenyl)ethenyl 4-methoxybenzoate Chemical compound C1=CC(OC)=CC=C1C(=O)OC(=C)C1=CC=C(C(C)(C)C)C=C1 ZUWVYBDTVBJNOX-UHFFFAOYSA-N 0.000 claims description 2
• BZCHPVAMTSYIKJ-UHFFFAOYSA-N 1-phenylethenyl 4-tert-butylbenzoate Chemical compound C1=CC(C(C)(C)C)=CC=C1C(=O)OC(=C)C1=CC=CC=C1 BZCHPVAMTSYIKJ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
• 125000004429 atom Chemical group 0.000 claims description 2
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• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
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• JMHCCAYJTTWMCX-QWPJCUCISA-M sodium;(2s)-2-amino-3-[4-(4-hydroxy-3,5-diiodophenoxy)-3,5-diiodophenyl]propanoate;pentahydrate Chemical compound O.O.O.O.O.[Na+].IC1=CC(C[C@H](N)C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 JMHCCAYJTTWMCX-QWPJCUCISA-M 0.000 claims description 2
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