ZA200403282B - Pharmaceutical and cosmetic compositions containing oxy group-bearing aromatic aldehydes. - Google Patents
Pharmaceutical and cosmetic compositions containing oxy group-bearing aromatic aldehydes. Download PDFInfo
- Publication number
- ZA200403282B ZA200403282B ZA200403282A ZA200403282A ZA200403282B ZA 200403282 B ZA200403282 B ZA 200403282B ZA 200403282 A ZA200403282 A ZA 200403282A ZA 200403282 A ZA200403282 A ZA 200403282A ZA 200403282 B ZA200403282 B ZA 200403282B
- Authority
- ZA
- South Africa
- Prior art keywords
- hydroxybenzaldehyde
- composition
- butyl
- compound
- hydroxy
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 120
- 239000002537 cosmetic Substances 0.000 title claims abstract description 37
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 title abstract description 12
- 150000003934 aromatic aldehydes Chemical class 0.000 title description 35
- -1 aromatic aldehyde compounds Chemical class 0.000 claims abstract description 38
- 230000000699 topical effect Effects 0.000 claims abstract description 26
- 230000009885 systemic effect Effects 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 80
- JRHHJNMASOIRDS-UHFFFAOYSA-N 4-ethoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1 JRHHJNMASOIRDS-UHFFFAOYSA-N 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 239000008194 pharmaceutical composition Substances 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 17
- 125000002947 alkylene group Chemical group 0.000 claims description 16
- 239000007788 liquid Substances 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- CSJDCSCTVDEHRN-UHFFFAOYSA-N methane;molecular oxygen Chemical compound C.O=O CSJDCSCTVDEHRN-UHFFFAOYSA-N 0.000 claims description 12
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 150000001241 acetals Chemical class 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 239000006071 cream Substances 0.000 claims description 10
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 claims description 10
- QZMGMXBYJZVAJN-UHFFFAOYSA-N 3-ethoxybenzaldehyde Chemical compound CCOC1=CC=CC(C=O)=C1 QZMGMXBYJZVAJN-UHFFFAOYSA-N 0.000 claims description 9
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims description 9
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 9
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 9
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 9
- 239000007787 solid Substances 0.000 claims description 9
- 208000027866 inflammatory disease Diseases 0.000 claims description 8
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 7
- 239000002552 dosage form Substances 0.000 claims description 7
- TYNJQOJWNMZQFZ-UHFFFAOYSA-N 4-prop-2-enoxybenzaldehyde Chemical compound C=CCOC1=CC=C(C=O)C=C1 TYNJQOJWNMZQFZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 claims description 5
- DUVJMSPTZMCSTQ-UHFFFAOYSA-N 2-ethoxybenzaldehyde Chemical compound CCOC1=CC=CC=C1C=O DUVJMSPTZMCSTQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- PYVBGEUEQLAGGN-UHFFFAOYSA-N 2,3,6-trihydroxybenzaldehyde Chemical compound OC1=CC=C(O)C(C=O)=C1O PYVBGEUEQLAGGN-UHFFFAOYSA-N 0.000 claims description 4
- OJZYLUUHIAKDJT-UHFFFAOYSA-N 2,3-dihydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1O OJZYLUUHIAKDJT-UHFFFAOYSA-N 0.000 claims description 4
- JIVGSHFYXPRRSZ-UHFFFAOYSA-N 2,3-dimethoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1OC JIVGSHFYXPRRSZ-UHFFFAOYSA-N 0.000 claims description 4
- BTQAJGSMXCDDAJ-UHFFFAOYSA-N 2,4,6-trihydroxybenzaldehyde Chemical compound OC1=CC(O)=C(C=O)C(O)=C1 BTQAJGSMXCDDAJ-UHFFFAOYSA-N 0.000 claims description 4
- LJFQTUKKYWDRAT-UHFFFAOYSA-N 2,4-dihydroxy-6-methylbenzaldehyde Chemical compound CC1=CC(O)=CC(O)=C1C=O LJFQTUKKYWDRAT-UHFFFAOYSA-N 0.000 claims description 4
- CLFRCXCBWIQVRN-UHFFFAOYSA-N 2,5-dihydroxybenzaldehyde Chemical compound OC1=CC=C(O)C(C=O)=C1 CLFRCXCBWIQVRN-UHFFFAOYSA-N 0.000 claims description 4
- WZUODJNEIXSNEU-UHFFFAOYSA-N 2-Hydroxy-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(O)=C1 WZUODJNEIXSNEU-UHFFFAOYSA-N 0.000 claims description 4
- RZXUCEISQDQBBF-UHFFFAOYSA-N 2-ethyl-6-hydroxybenzaldehyde Chemical compound CCC1=CC=CC(O)=C1C=O RZXUCEISQDQBBF-UHFFFAOYSA-N 0.000 claims description 4
- RGZHEOWNTDJLAQ-UHFFFAOYSA-N 3,4,5-trihydroxybenzaldehyde Chemical compound OC1=CC(C=O)=CC(O)=C1O RGZHEOWNTDJLAQ-UHFFFAOYSA-N 0.000 claims description 4
- SSTRYEXQYQGGAS-UHFFFAOYSA-N 3,4-diethoxybenzaldehyde Chemical compound CCOC1=CC=C(C=O)C=C1OCC SSTRYEXQYQGGAS-UHFFFAOYSA-N 0.000 claims description 4
- HAQLHRYUDBKTJG-UHFFFAOYSA-N 3,5-dihydroxybenzaldehyde Chemical compound OC1=CC(O)=CC(C=O)=C1 HAQLHRYUDBKTJG-UHFFFAOYSA-N 0.000 claims description 4
- WYVGYYIZXPXHAZ-UHFFFAOYSA-N 3-chloro-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1Cl WYVGYYIZXPXHAZ-UHFFFAOYSA-N 0.000 claims description 4
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 claims description 4
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 claims description 4
- NSLDZVUVKUIYNL-UHFFFAOYSA-N 4-Isopropyl-salicylaldehyd Natural products CC(C)C1=CC=C(C=O)C(O)=C1 NSLDZVUVKUIYNL-UHFFFAOYSA-N 0.000 claims description 4
- UYGBSRJODQHNLQ-UHFFFAOYSA-N 4-hydroxy-3,5-dimethylbenzaldehyde Chemical compound CC1=CC(C=O)=CC(C)=C1O UYGBSRJODQHNLQ-UHFFFAOYSA-N 0.000 claims description 4
- YAPVGSXODFOBBR-UHFFFAOYSA-N 4-pentoxybenzaldehyde Chemical compound CCCCCOC1=CC=C(C=O)C=C1 YAPVGSXODFOBBR-UHFFFAOYSA-N 0.000 claims description 4
- WGQVKYPDHREEJU-UHFFFAOYSA-N 5-acetyl-2-methoxybenzaldehyde Natural products COC1=CC=C(C(C)=O)C=C1C=O WGQVKYPDHREEJU-UHFFFAOYSA-N 0.000 claims description 4
- UTCFOFWMEPQCSR-UHFFFAOYSA-N 5-formylsalicylic acid Chemical compound OC(=O)C1=CC(C=O)=CC=C1O UTCFOFWMEPQCSR-UHFFFAOYSA-N 0.000 claims description 4
- ZRUOTKQBVMWMDK-UHFFFAOYSA-N 6-Oxy-2-methyl-benzaldehyd Natural products CC1=CC=CC(O)=C1C=O ZRUOTKQBVMWMDK-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- MGMUFSXXHCQPGA-UHFFFAOYSA-N fomecin A Natural products OCC1=CC(O)=C(O)C(O)=C1C=O MGMUFSXXHCQPGA-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 4
- 238000013268 sustained release Methods 0.000 claims description 4
- 239000012730 sustained-release form Substances 0.000 claims description 4
- KCDXJAYRVLXPFO-UHFFFAOYSA-N syringaldehyde Chemical compound COC1=CC(C=O)=CC(OC)=C1O KCDXJAYRVLXPFO-UHFFFAOYSA-N 0.000 claims description 4
- COBXDAOIDYGHGK-UHFFFAOYSA-N syringaldehyde Natural products COC1=CC=C(C=O)C(OC)=C1O COBXDAOIDYGHGK-UHFFFAOYSA-N 0.000 claims description 4
- XRERBLZFZMBKRU-UHFFFAOYSA-N (2-formyl-6-methoxyphenyl) acetate Chemical compound COC1=CC=CC(C=O)=C1OC(C)=O XRERBLZFZMBKRU-UHFFFAOYSA-N 0.000 claims description 3
- HEVMDQBCAHEHDY-UHFFFAOYSA-N (Dimethoxymethyl)benzene Chemical compound COC(OC)C1=CC=CC=C1 HEVMDQBCAHEHDY-UHFFFAOYSA-N 0.000 claims description 3
- XHWMNHADTZZHGI-UHFFFAOYSA-N 4-butoxybenzaldehyde Chemical compound CCCCOC1=CC=C(C=O)C=C1 XHWMNHADTZZHGI-UHFFFAOYSA-N 0.000 claims description 3
- GWXUVWKBVROFDM-UHFFFAOYSA-N 4-hexoxybenzaldehyde Chemical compound CCCCCCOC1=CC=C(C=O)C=C1 GWXUVWKBVROFDM-UHFFFAOYSA-N 0.000 claims description 3
- FGXZWMCBNMMYPL-UHFFFAOYSA-N 4-propoxybenzaldehyde Chemical compound CCCOC1=CC=C(C=O)C=C1 FGXZWMCBNMMYPL-UHFFFAOYSA-N 0.000 claims description 3
- BWKDAAFSXYPQOS-UHFFFAOYSA-N Benzaldehyde glyceryl acetal Chemical compound O1CC(O)COC1C1=CC=CC=C1 BWKDAAFSXYPQOS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- XJNUECKWDBNFJV-UHFFFAOYSA-N hexadecyl 2-ethylhexanoate Chemical compound CCCCCCCCCCCCCCCCOC(=O)C(CC)CCCC XJNUECKWDBNFJV-UHFFFAOYSA-N 0.000 claims description 3
- HHFQQGZFRGSXCR-UHFFFAOYSA-N (3-bromo-2-formyl-6-methoxyphenyl) acetate Chemical compound COC1=CC=C(Br)C(C=O)=C1OC(C)=O HHFQQGZFRGSXCR-UHFFFAOYSA-N 0.000 claims description 2
- UVJGEUFORIIASL-UHFFFAOYSA-N 2,3,4,5-tetramethoxybenzaldehyde Chemical compound COC1=CC(C=O)=C(OC)C(OC)=C1OC UVJGEUFORIIASL-UHFFFAOYSA-N 0.000 claims description 2
- KTLUDVLHAZMWIN-UHFFFAOYSA-N 2,3,4-trihydroxy-6-(hydroxymethyl)-5-methylbenzaldehyde Chemical compound CC1=C(O)C(O)=C(O)C(C=O)=C1CO KTLUDVLHAZMWIN-UHFFFAOYSA-N 0.000 claims description 2
- HUTITODAYBWJRG-UHFFFAOYSA-N 2,3,5-trihydroxybenzaldehyde Chemical compound OC1=CC(O)=C(O)C(C=O)=C1 HUTITODAYBWJRG-UHFFFAOYSA-N 0.000 claims description 2
- OQEPUQXAJPNVFJ-UHFFFAOYSA-N 2,4,5-triethoxybenzaldehyde Chemical compound CCOC1=CC(OCC)=C(C=O)C=C1OCC OQEPUQXAJPNVFJ-UHFFFAOYSA-N 0.000 claims description 2
- IAJBQAYHSQIQRE-UHFFFAOYSA-N 2,4,5-trimethoxybenzaldehyde Chemical compound COC1=CC(OC)=C(C=O)C=C1OC IAJBQAYHSQIQRE-UHFFFAOYSA-N 0.000 claims description 2
- AOPMHYFEQDBXPZ-UHFFFAOYSA-N 2,4-dihydroxy-3-methylbenzaldehyde Chemical compound CC1=C(O)C=CC(C=O)=C1O AOPMHYFEQDBXPZ-UHFFFAOYSA-N 0.000 claims description 2
- HIZQQWKWEYMFMU-UHFFFAOYSA-N 2,4-dihydroxy-5-propylbenzaldehyde Chemical compound CCCC1=CC(C=O)=C(O)C=C1O HIZQQWKWEYMFMU-UHFFFAOYSA-N 0.000 claims description 2
- YSIIHTHHMPYKFP-UHFFFAOYSA-N 2,5-dimethoxyterephthalaldehyde Chemical compound COC1=CC(C=O)=C(OC)C=C1C=O YSIIHTHHMPYKFP-UHFFFAOYSA-N 0.000 claims description 2
- KBHRXHKEQPXIOQ-UHFFFAOYSA-N 2,5-ditert-butyl-3-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C(C=O)=C1 KBHRXHKEQPXIOQ-UHFFFAOYSA-N 0.000 claims description 2
- ROAQMGJHSNIROA-UHFFFAOYSA-N 2,6-difluoro-4-hydroxybenzaldehyde Chemical compound OC1=CC(F)=C(C=O)C(F)=C1 ROAQMGJHSNIROA-UHFFFAOYSA-N 0.000 claims description 2
- DGXAGETVRDOQFP-UHFFFAOYSA-N 2,6-dihydroxybenzaldehyde Chemical compound OC1=CC=CC(O)=C1C=O DGXAGETVRDOQFP-UHFFFAOYSA-N 0.000 claims description 2
- DMBULVGXPRMQJZ-UHFFFAOYSA-N 2-(2-formyl-6-hydroxyphenyl)acetic acid Chemical compound OC(=O)CC1=C(O)C=CC=C1C=O DMBULVGXPRMQJZ-UHFFFAOYSA-N 0.000 claims description 2
- OUVHTVQMYDOGEJ-UHFFFAOYSA-N 2-(3-formyl-4-hydroxy-5-iodophenyl)acetic acid Chemical compound OC(=O)CC1=CC(I)=C(O)C(C=O)=C1 OUVHTVQMYDOGEJ-UHFFFAOYSA-N 0.000 claims description 2
- JODRRPJMQDFCBJ-UHFFFAOYSA-N 2-Hydroxy-4-methylbenzaldehyde Chemical compound CC1=CC=C(C=O)C(O)=C1 JODRRPJMQDFCBJ-UHFFFAOYSA-N 0.000 claims description 2
- QAAAQOUVBQAONT-UHFFFAOYSA-N 2-butan-2-yl-3-hydroxybenzaldehyde Chemical compound CCC(C)C1=C(O)C=CC=C1C=O QAAAQOUVBQAONT-UHFFFAOYSA-N 0.000 claims description 2
- DKIGCUHERJFJPT-UHFFFAOYSA-N 2-butan-2-yl-4-hydroxybenzaldehyde Chemical compound CCC(C)C1=CC(O)=CC=C1C=O DKIGCUHERJFJPT-UHFFFAOYSA-N 0.000 claims description 2
- CZKLXTAYVRAYSM-UHFFFAOYSA-N 2-butan-2-yl-5-hydroxybenzaldehyde Chemical compound CCC(C)C1=CC=C(O)C=C1C=O CZKLXTAYVRAYSM-UHFFFAOYSA-N 0.000 claims description 2
- YQBPYQWAVVNXGN-UHFFFAOYSA-N 2-butan-2-yl-6-hydroxybenzaldehyde Chemical compound CCC(C)C1=CC=CC(O)=C1C=O YQBPYQWAVVNXGN-UHFFFAOYSA-N 0.000 claims description 2
- FSMCOBJDZVRWIZ-UHFFFAOYSA-N 2-butoxybenzaldehyde Chemical compound CCCCOC1=CC=CC=C1C=O FSMCOBJDZVRWIZ-UHFFFAOYSA-N 0.000 claims description 2
- VHUFXQNTGQOYJE-UHFFFAOYSA-N 2-butyl-3-hydroxybenzaldehyde Chemical compound CCCCC1=C(O)C=CC=C1C=O VHUFXQNTGQOYJE-UHFFFAOYSA-N 0.000 claims description 2
- AYMIULGCGRCDGH-UHFFFAOYSA-N 2-butyl-4-hydroxybenzaldehyde Chemical compound CCCCC1=CC(O)=CC=C1C=O AYMIULGCGRCDGH-UHFFFAOYSA-N 0.000 claims description 2
- HHYGVSRDQGCAHI-UHFFFAOYSA-N 2-butyl-5-hydroxybenzaldehyde Chemical compound CCCCC1=CC=C(O)C=C1C=O HHYGVSRDQGCAHI-UHFFFAOYSA-N 0.000 claims description 2
- BHJGGCXLUAXILW-UHFFFAOYSA-N 2-butyl-6-hydroxybenzaldehyde Chemical compound CCCCC1=CC=CC(O)=C1C=O BHJGGCXLUAXILW-UHFFFAOYSA-N 0.000 claims description 2
- UQPRTBWIRGBPGV-UHFFFAOYSA-N 2-ethoxy-3-methylbenzaldehyde Chemical compound CCOC1=C(C)C=CC=C1C=O UQPRTBWIRGBPGV-UHFFFAOYSA-N 0.000 claims description 2
- NKVRHHKKXMGBJV-UHFFFAOYSA-N 2-ethyl-3-hydroxybenzaldehyde Chemical compound CCC1=C(O)C=CC=C1C=O NKVRHHKKXMGBJV-UHFFFAOYSA-N 0.000 claims description 2
- NHONMDAFARLXAU-UHFFFAOYSA-N 2-ethyl-4-hydroxybenzaldehyde Chemical compound CCC1=CC(O)=CC=C1C=O NHONMDAFARLXAU-UHFFFAOYSA-N 0.000 claims description 2
- BALPZBRZKJGPBI-UHFFFAOYSA-N 2-ethyl-5-hydroxybenzaldehyde Chemical compound CCC1=CC=C(O)C=C1C=O BALPZBRZKJGPBI-UHFFFAOYSA-N 0.000 claims description 2
- YJURXDOMUKMZAW-UHFFFAOYSA-N 2-fluoro-4-heptoxybenzaldehyde Chemical compound CCCCCCCOC1=CC=C(C=O)C(F)=C1 YJURXDOMUKMZAW-UHFFFAOYSA-N 0.000 claims description 2
- UNWQNFJBBWXFBG-UHFFFAOYSA-N 2-fluoro-4-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C(F)=C1 UNWQNFJBBWXFBG-UHFFFAOYSA-N 0.000 claims description 2
- XAGXEOPGTCVAMO-UHFFFAOYSA-N 2-fluoro-4-octoxybenzaldehyde Chemical compound CCCCCCCCOC1=CC=C(C=O)C(F)=C1 XAGXEOPGTCVAMO-UHFFFAOYSA-N 0.000 claims description 2
- NZBOQMZBKQXWRM-UHFFFAOYSA-N 2-hydroxy-3,4-bis(2-methylpropyl)benzaldehyde Chemical compound CC(C)CC1=CC=C(C=O)C(O)=C1CC(C)C NZBOQMZBKQXWRM-UHFFFAOYSA-N 0.000 claims description 2
- MYWSBJKVOUZCIA-UHFFFAOYSA-N 2-hydroxy-3,5-diiodobenzaldehyde Chemical compound OC1=C(I)C=C(I)C=C1C=O MYWSBJKVOUZCIA-UHFFFAOYSA-N 0.000 claims description 2
- RYYFQEATZPXCRA-UHFFFAOYSA-N 2-hydroxy-3-pentylbenzaldehyde Chemical compound CCCCCC1=CC=CC(C=O)=C1O RYYFQEATZPXCRA-UHFFFAOYSA-N 0.000 claims description 2
- ORJQGHNTYRXBJF-UHFFFAOYSA-N 2-hydroxy-3-propan-2-ylbenzaldehyde Chemical compound CC(C)C1=CC=CC(C=O)=C1O ORJQGHNTYRXBJF-UHFFFAOYSA-N 0.000 claims description 2
- BXHJYWXFFYWVIB-UHFFFAOYSA-N 2-hydroxy-3-propylbenzaldehyde Chemical compound CCCC1=CC=CC(C=O)=C1O BXHJYWXFFYWVIB-UHFFFAOYSA-N 0.000 claims description 2
- NZSYHSVSKGKFGO-UHFFFAOYSA-N 2-hydroxy-4-pentylbenzaldehyde Chemical compound CCCCCC1=CC=C(C=O)C(O)=C1 NZSYHSVSKGKFGO-UHFFFAOYSA-N 0.000 claims description 2
- VXAIVKUOFLCWFG-UHFFFAOYSA-N 2-hydroxy-4-propylbenzaldehyde Chemical compound CCCC1=CC=C(C=O)C(O)=C1 VXAIVKUOFLCWFG-UHFFFAOYSA-N 0.000 claims description 2
- ILEIUTCVWLYZOM-UHFFFAOYSA-N 2-hydroxy-5-methylbenzaldehyde Chemical compound CC1=CC=C(O)C(C=O)=C1 ILEIUTCVWLYZOM-UHFFFAOYSA-N 0.000 claims description 2
- AGBHCLFWMAZZBP-UHFFFAOYSA-N 2-hydroxy-5-pentylbenzaldehyde Chemical compound CCCCCC1=CC=C(O)C(C=O)=C1 AGBHCLFWMAZZBP-UHFFFAOYSA-N 0.000 claims description 2
- OUAWQHGDAGFMAW-UHFFFAOYSA-N 2-hydroxy-5-propan-2-ylbenzaldehyde Chemical compound CC(C)C1=CC=C(O)C(C=O)=C1 OUAWQHGDAGFMAW-UHFFFAOYSA-N 0.000 claims description 2
- CECMKFMRWXFCND-UHFFFAOYSA-N 2-hydroxy-5-propylbenzaldehyde Chemical compound CCCC1=CC=C(O)C(C=O)=C1 CECMKFMRWXFCND-UHFFFAOYSA-N 0.000 claims description 2
- DZJPDDVDKXHRLF-UHFFFAOYSA-N 2-hydroxy-6-methoxybenzaldehyde Chemical compound COC1=CC=CC(O)=C1C=O DZJPDDVDKXHRLF-UHFFFAOYSA-N 0.000 claims description 2
- BQOOOIWYODEKBR-UHFFFAOYSA-N 2-hydroxy-6-pentadec-8-enylbenzaldehyde Chemical compound CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1C=O BQOOOIWYODEKBR-UHFFFAOYSA-N 0.000 claims description 2
- GJDWAHAWINSCPM-UHFFFAOYSA-N 2-hydroxy-6-pentylbenzaldehyde Chemical compound CCCCCC1=CC=CC(O)=C1C=O GJDWAHAWINSCPM-UHFFFAOYSA-N 0.000 claims description 2
- PUHBMFQIBBOZJF-UHFFFAOYSA-N 2-hydroxy-6-propan-2-ylbenzaldehyde Chemical compound CC(C)C1=CC=CC(O)=C1C=O PUHBMFQIBBOZJF-UHFFFAOYSA-N 0.000 claims description 2
- VDWOZURFSFCGSK-UHFFFAOYSA-N 2-hydroxy-6-propylbenzaldehyde Chemical compound CCCC1=CC=CC(O)=C1C=O VDWOZURFSFCGSK-UHFFFAOYSA-N 0.000 claims description 2
- VNSQYSFEIBZPHF-UHFFFAOYSA-N 2-methoxy-3-methylbenzaldehyde Chemical compound COC1=C(C)C=CC=C1C=O VNSQYSFEIBZPHF-UHFFFAOYSA-N 0.000 claims description 2
- 239000001431 2-methylbenzaldehyde Substances 0.000 claims description 2
- ZZJVNPRHHLLANO-UHFFFAOYSA-N 2-propan-2-yloxybenzaldehyde Chemical compound CC(C)OC1=CC=CC=C1C=O ZZJVNPRHHLLANO-UHFFFAOYSA-N 0.000 claims description 2
- CDUPASLURGOXGD-UHFFFAOYSA-N 2-propoxybenzaldehyde Chemical compound CCCOC1=CC=CC=C1C=O CDUPASLURGOXGD-UHFFFAOYSA-N 0.000 claims description 2
- OPKCYHUJMQNZJV-UHFFFAOYSA-N 2-tert-butyl-3-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=C(O)C=CC=C1C=O OPKCYHUJMQNZJV-UHFFFAOYSA-N 0.000 claims description 2
- IOWYSQRPEGKPBP-UHFFFAOYSA-N 2-tert-butyl-4-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC(O)=CC=C1C=O IOWYSQRPEGKPBP-UHFFFAOYSA-N 0.000 claims description 2
- SEPGHKOMIBAOSI-UHFFFAOYSA-N 2-tert-butyl-5-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC=C(O)C=C1C=O SEPGHKOMIBAOSI-UHFFFAOYSA-N 0.000 claims description 2
- BSOXVRQPIPFIDU-UHFFFAOYSA-N 3,4,5-trihydroxyphthalaldehyde Chemical compound OC1=CC(C=O)=C(C=O)C(O)=C1O BSOXVRQPIPFIDU-UHFFFAOYSA-N 0.000 claims description 2
- SPYSTZXWVZFPBG-UHFFFAOYSA-N 3,4-ditert-butyl-2-hydroxybenzaldehyde Chemical compound CC(C)(C)C1=CC=C(C=O)C(O)=C1C(C)(C)C SPYSTZXWVZFPBG-UHFFFAOYSA-N 0.000 claims description 2
- FABVMBDCVAJXMB-UHFFFAOYSA-N 3,5-dichloro-2-hydroxybenzaldehyde Chemical compound OC1=C(Cl)C=C(Cl)C=C1C=O FABVMBDCVAJXMB-UHFFFAOYSA-N 0.000 claims description 2
- QGSAZWCEHUYVMW-UHFFFAOYSA-N 3,5-difluoro-2-hydroxybenzaldehyde Chemical compound OC1=C(F)C=C(F)C=C1C=O QGSAZWCEHUYVMW-UHFFFAOYSA-N 0.000 claims description 2
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- A61P17/00—Drugs for dermatological disorders
- A61P17/12—Keratolytics, e.g. wart or anti-corn preparations
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- 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
- A61P17/14—Drugs for dermatological disorders for baldness or alopecia
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- 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
- A61P17/16—Emollients or protectives, e.g. against radiation
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Birds (AREA)
- Emergency Medicine (AREA)
- Pulmonology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Toxicology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33227701P | 2001-11-16 | 2001-11-16 | |
| US34604902P | 2002-01-04 | 2002-01-04 | |
| US36851802P | 2002-04-01 | 2002-04-01 | |
| US36856502P | 2002-04-01 | 2002-04-01 | |
| US38469002P | 2002-05-30 | 2002-05-30 | |
| US38458902P | 2002-05-30 | 2002-05-30 | |
| PCT/US2002/021844 WO2003043621A1 (en) | 2001-11-16 | 2002-08-16 | Pharmaceutical and cosmetic compositions containing oxy group-bearing aromatic aldehydes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200403282B true ZA200403282B (en) | 2005-05-03 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200403282A ZA200403282B (en) | 2001-11-16 | 2004-04-30 | Pharmaceutical and cosmetic compositions containing oxy group-bearing aromatic aldehydes. |
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| EP (1) | EP1443915B1 (xx) |
| JP (2) | JP4587669B2 (xx) |
| KR (1) | KR100887601B1 (xx) |
| CN (2) | CN1589136A (xx) |
| AT (1) | ATE330591T1 (xx) |
| AU (1) | AU2002326363B2 (xx) |
| BR (1) | BR0214208A (xx) |
| CA (1) | CA2464867C (xx) |
| DE (1) | DE60212683T2 (xx) |
| DK (1) | DK1443915T3 (xx) |
| EA (1) | EA009281B1 (xx) |
| ES (1) | ES2266554T3 (xx) |
| IL (2) | IL161545A0 (xx) |
| MX (1) | MXPA04004673A (xx) |
| NZ (1) | NZ552216A (xx) |
| PT (1) | PT1443915E (xx) |
| TW (1) | TWI297604B (xx) |
| WO (1) | WO2003043621A1 (xx) |
| ZA (1) | ZA200403282B (xx) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US8246969B2 (en) | 2001-11-16 | 2012-08-21 | Skinmedica, Inc. | Compositions containing aromatic aldehydes and their use in treatments |
| US20040254252A1 (en) * | 2003-05-15 | 2004-12-16 | Engles Charles R. | Compositions containing a combination of a pharmaceutical agent or a cosmetic agent and an oxy group-bearing aromatic aldehyde and their use in treatments |
| CA2549025A1 (en) | 2003-08-01 | 2005-02-10 | Janssen Pharmaceutica N.V. | Substituted indole-o-glucosides |
| PT1651658E (pt) | 2003-08-01 | 2013-03-07 | Mitsubishi Tanabe Pharma Corp | Novos compostos que possuem actividade inibidora dirigida contra os transportadores dependentes do sódio |
| US8785403B2 (en) | 2003-08-01 | 2014-07-22 | Mitsubishi Tanabe Pharma Corporation | Glucopyranoside compound |
| WO2007002447A2 (en) * | 2005-06-23 | 2007-01-04 | Bioform Medical, Inc. | Compositions for treating rosacea |
| GB0526283D0 (en) * | 2005-12-23 | 2006-02-01 | Givaudan Sa | Compositions |
| UY30730A1 (es) | 2006-12-04 | 2008-07-03 | Mitsubishi Tanabe Pharma Corp | Forma cristalina del hemihidrato de 1-(b (beta)-d-glucopiranosil) -4-metil-3-[5-(4-fluorofenil) -2-tienilmetil]benceno |
| UA105480C2 (uk) | 2007-09-10 | 2014-05-26 | Янссен Фармацевтика Н.В. | Спосіб одержання сполук, які застосовують як інгібітори натрійзалежного переносника глюкози |
| CA2740200C (en) * | 2007-10-10 | 2015-01-13 | Therametics, Llc | Methods and compositions for treating dermatological diseases and conditions |
| US9616006B2 (en) | 2007-10-10 | 2017-04-11 | DermaMedics, LLC | Methods and compositions for treating dermatological diseases and conditions |
| CL2008003653A1 (es) | 2008-01-17 | 2010-03-05 | Mitsubishi Tanabe Pharma Corp | Uso de un inhibidor de sglt derivado de glucopiranosilo y un inhibidor de dppiv seleccionado para tratar la diabetes; y composicion farmaceutica. |
| US9056850B2 (en) | 2008-10-17 | 2015-06-16 | Janssen Pharmaceutica N.V. | Process for the preparation of compounds useful as inhibitors of SGLT |
| US20110009347A1 (en) | 2009-07-08 | 2011-01-13 | Yin Liang | Combination therapy for the treatment of diabetes |
| DK2488515T3 (en) | 2009-10-14 | 2017-02-27 | Janssen Pharmaceutica Nv | PROCEDURE FOR THE PREPARATION OF COMPOUNDS USED AS INHIBITORS OF SGLT2 |
| HUE029853T2 (en) | 2010-05-11 | 2017-04-28 | Janssen Pharmaceutica Nv | Pharmaceutical formulations containing 1- (beta-D-Glucopyranosyl) -2-thienylmethylbenzene derivatives as SGLT inhibitors |
| AU2012204164A1 (en) * | 2011-01-07 | 2013-07-25 | Allergan, Inc. | Melanin modification compositions and methods of use |
| CA2832938C (en) | 2011-04-13 | 2019-09-03 | Janssen Pharmaceutica Nv | Process for the preparation of compounds useful as inhibitors of sglt2 |
| US9035044B2 (en) | 2011-05-09 | 2015-05-19 | Janssen Pharmaceutica Nv | L-proline and citric acid co-crystals of (2S, 3R, 4R, 5S,6R)-2-(3-((5-(4-fluorophenyl)thiopen-2-yl)methyl)4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol |
| JP6061373B2 (ja) * | 2012-07-24 | 2017-01-18 | 国立研究開発法人産業技術総合研究所 | ２−ヒドロキシベンズアルデヒド化合物、これを含有するコラーゲン細胞外分泌阻害剤及び医薬品組成物 |
| CN104473912A (zh) * | 2014-11-26 | 2015-04-01 | 云南中医学院 | 对羟基苯甲醛在制备抗炎药物中的用途 |
| US20170071970A1 (en) | 2015-09-15 | 2017-03-16 | Janssen Pharmaceutica Nv | Co-therapy comprising canagliflozin and phentermine for the treatment of obesity and obesity related disorders |
| JP2019116426A (ja) * | 2017-12-26 | 2019-07-18 | 小林製薬株式会社 | 歯肉組織の破壊抑制剤 |
| FR3081710A1 (fr) * | 2018-05-31 | 2019-12-06 | Bionuclei | Molecule enzymatique mimant une activite antioxydante |
| GB201817785D0 (en) * | 2018-10-31 | 2018-12-19 | Givaudan Sa | Organic compounds |
| WO2022128054A1 (en) * | 2020-12-14 | 2022-06-23 | Symrise Ag | Medicament for fighting inflammatory conditions of human skin (iv) |
| WO2022128051A1 (en) * | 2020-12-14 | 2022-06-23 | Symrise Ag | Medicament for fighting inflammatory conditions of human skin (ii) |
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| US414770A (en) * | 1889-11-12 | Swaging-bench for iron fences | ||
| JPS5244375B2 (xx) * | 1974-04-19 | 1977-11-08 | ||
| DE2519161A1 (de) * | 1975-04-30 | 1976-11-18 | Henkel & Cie Gmbh | Entzuendungshemmer fuer kosmetische praeparationen |
| JPS604801B2 (ja) * | 1977-11-21 | 1985-02-06 | 呉羽化学工業株式会社 | 抗皮膚真菌剤 |
| JPS5545659A (en) * | 1978-09-28 | 1980-03-31 | Rikagaku Kenkyusho | Carcinostatic agent |
| JPS5545656A (en) * | 1978-09-28 | 1980-03-31 | Rikagaku Kenkyusho | Carcinostatic agent |
| JPS5612310A (en) * | 1979-07-10 | 1981-02-06 | Rikagaku Kenkyusho | Carcinostatic agent |
| GB8501646D0 (en) * | 1985-01-23 | 1985-02-27 | Nipa Lab Ltd | Control of micro-organisms |
| US4714609A (en) * | 1986-07-21 | 1987-12-22 | Laverne Stanley | Skin tanning composition |
| JPH085780B2 (ja) * | 1989-04-28 | 1996-01-24 | 呉羽化学工業株式会社 | 変形性関節症治療剤 |
| CA2017923A1 (en) * | 1989-06-06 | 1990-12-06 | Gordon Francis Brunner | Heated oral antitussive compositions |
| GB9026080D0 (en) * | 1990-11-30 | 1991-01-16 | Norsk Hydro As | Pharmaceutical compositions |
| JP3057207B2 (ja) * | 1991-09-03 | 2000-06-26 | 株式会社資生堂 | 皮膚外用剤 |
| US5378468A (en) * | 1992-09-22 | 1995-01-03 | The Mennen Company | Composition containing body activated fragrance for contacting the skin and method of use |
| JPH072640A (ja) * | 1992-10-29 | 1995-01-06 | Marino Forum 21 | 紫外線障害防御外用剤 |
| JPH06329516A (ja) * | 1993-05-21 | 1994-11-29 | Mikimoto Pharmaceut Co Ltd | 化粧料 |
| GB9314929D0 (en) * | 1993-07-19 | 1993-09-01 | Charwell Consumer Prod | Louse repellent compositions |
| JPH07242558A (ja) * | 1994-03-05 | 1995-09-19 | Tomoji Tanaka | 床ズレ防止剤添加体 |
| JP3665360B2 (ja) * | 1994-05-02 | 2005-06-29 | ポーラ化成工業株式会社 | 活性酸素消去剤及びこれを含む組成物 |
| US5614179A (en) * | 1995-09-27 | 1997-03-25 | Church & Dwight Co., Inc. | Cosmetic deodorant products containing a polymer/fragrance-encapsulated bicarbonate ingredient |
| US5733535A (en) * | 1995-10-25 | 1998-03-31 | The Procter & Gamble Co. | Topical compositions containing N-acetylcysteine and odor masking materials |
| US6086903A (en) * | 1996-02-26 | 2000-07-11 | The Proctor & Gamble Company | Personal treatment compositions and/or cosmetic compositions containing enduring perfume |
| US5766575A (en) * | 1996-06-14 | 1998-06-16 | Chesebrough-Pond's Usa Co., Division Of Conopco, Inc. | Method and composition for skin lightening |
| US5668182A (en) * | 1996-08-19 | 1997-09-16 | Virginia Commonwealth University | Method of calming or sedating an animal with a hydroxy benzaldehyde compound |
| US6126930A (en) * | 1997-02-13 | 2000-10-03 | The Procter & Gamble Company | Spray compositions |
| WO1998041185A1 (fr) * | 1997-03-18 | 1998-09-24 | Kao Corporation | Composition a appliquer sur les cheveux ou sur la peau |
| US6214879B1 (en) * | 1998-03-24 | 2001-04-10 | Virginia Commonwealth University | Allosteric inhibitors of pyruvate kinase |
| DE19841796A1 (de) * | 1998-09-12 | 2000-03-16 | Beiersdorf Ag | Kombinationen von Antiadhäsiva (Kohlenhydrate) und Mikrobiziden |
| JP2001106639A (ja) * | 1999-10-04 | 2001-04-17 | Taisho Pharmaceut Co Ltd | 経口用組成物 |
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2002
- 2002-08-16 IL IL16154502A patent/IL161545A0/xx unknown
- 2002-08-16 CA CA2464867A patent/CA2464867C/en not_active Expired - Lifetime
- 2002-08-16 AU AU2002326363A patent/AU2002326363B2/en not_active Expired
- 2002-08-16 PT PT02761067T patent/PT1443915E/pt unknown
- 2002-08-16 CN CNA028227166A patent/CN1589136A/zh active Pending
- 2002-08-16 KR KR1020047007429A patent/KR100887601B1/ko active IP Right Grant
- 2002-08-16 DK DK02761067T patent/DK1443915T3/da active
- 2002-08-16 AT AT02761067T patent/ATE330591T1/de active
- 2002-08-16 NZ NZ552216A patent/NZ552216A/en not_active IP Right Cessation
- 2002-08-16 DE DE60212683T patent/DE60212683T2/de not_active Expired - Lifetime
- 2002-08-16 ES ES02761067T patent/ES2266554T3/es not_active Expired - Lifetime
- 2002-08-16 MX MXPA04004673A patent/MXPA04004673A/es active IP Right Grant
- 2002-08-16 JP JP2003545302A patent/JP4587669B2/ja not_active Expired - Lifetime
- 2002-08-16 WO PCT/US2002/021844 patent/WO2003043621A1/en active IP Right Grant
- 2002-08-16 BR BR0214208-2A patent/BR0214208A/pt not_active IP Right Cessation
- 2002-08-16 EA EA200400689A patent/EA009281B1/ru unknown
- 2002-08-16 CN CN2012102290813A patent/CN102973417A/zh active Pending
- 2002-08-16 EP EP02761067A patent/EP1443915B1/en not_active Expired - Lifetime
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2009
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Also Published As
| Publication number | Publication date |
|---|---|
| EP1443915A1 (en) | 2004-08-11 |
| ATE330591T1 (de) | 2006-07-15 |
| CN1589136A (zh) | 2005-03-02 |
| DE60212683D1 (de) | 2006-08-03 |
| DK1443915T3 (da) | 2006-10-23 |
| KR20050018633A (ko) | 2005-02-23 |
| ES2266554T3 (es) | 2007-03-01 |
| IL161545A (en) | 2010-11-30 |
| PT1443915E (pt) | 2006-11-30 |
| CA2464867C (en) | 2014-01-28 |
| JP2010059203A (ja) | 2010-03-18 |
| MXPA04004673A (es) | 2005-05-17 |
| KR100887601B1 (ko) | 2009-03-13 |
| WO2003043621A1 (en) | 2003-05-30 |
| DE60212683T2 (de) | 2007-06-28 |
| EP1443915B1 (en) | 2006-06-21 |
| AU2002326363A1 (en) | 2003-06-10 |
| TWI297604B (en) | 2008-06-11 |
| TW200406195A (en) | 2004-05-01 |
| NZ552216A (en) | 2008-07-31 |
| CA2464867A1 (en) | 2003-05-30 |
| JP4587669B2 (ja) | 2010-11-24 |
| IL161545A0 (en) | 2004-09-27 |
| AU2002326363B2 (en) | 2008-08-28 |
| JP2005509662A (ja) | 2005-04-14 |
| BR0214208A (pt) | 2004-10-26 |
| CN102973417A (zh) | 2013-03-20 |
| EA200400689A1 (ru) | 2005-02-24 |
| EA009281B1 (ru) | 2007-12-28 |
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