KR100947907B1 - 치환된 1,3-디페닐프로프-2-엔-1-온 유도체에 기초한조성물, 이의 제조 및 용도 - Google Patents
치환된 1,3-디페닐프로프-2-엔-1-온 유도체에 기초한조성물, 이의 제조 및 용도 Download PDFInfo
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- KR100947907B1 KR100947907B1 KR1020047021625A KR20047021625A KR100947907B1 KR 100947907 B1 KR100947907 B1 KR 100947907B1 KR 1020047021625 A KR1020047021625 A KR 1020047021625A KR 20047021625 A KR20047021625 A KR 20047021625A KR 100947907 B1 KR100947907 B1 KR 100947907B1
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- prop
- dimethyl
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- hydroxy
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- 239000000203 mixture Substances 0.000 title claims abstract description 65
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical class C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title description 7
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 9
- 208000008589 Obesity Diseases 0.000 claims abstract description 8
- 235000020824 obesity Nutrition 0.000 claims abstract description 8
- 201000011510 cancer Diseases 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 213
- 125000001424 substituent group Chemical group 0.000 claims description 50
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 36
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 27
- -1 thionitroso group Chemical group 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 125000004434 sulfur atom Chemical group 0.000 claims description 13
- 201000001320 Atherosclerosis Diseases 0.000 claims description 12
- 229910052717 sulfur Chemical group 0.000 claims description 12
- 208000024827 Alzheimer disease Diseases 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- 201000004681 Psoriasis Diseases 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 9
- 206010020751 Hypersensitivity Diseases 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 230000007815 allergy Effects 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 8
- 201000004624 Dermatitis Diseases 0.000 claims description 7
- 208000018737 Parkinson disease Diseases 0.000 claims description 7
- 208000003251 Pruritus Diseases 0.000 claims description 7
- 208000006673 asthma Diseases 0.000 claims description 7
- 208000010668 atopic eczema Diseases 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- JHQXCEBEGVCTTB-UHFFFAOYSA-N CSc1ccc(cc1)C(=O)C=Cc1cc(C)c(C(O)=O)c(C)c1OC(C)C Chemical compound CSc1ccc(cc1)C(=O)C=Cc1cc(C)c(C(O)=O)c(C)c1OC(C)C JHQXCEBEGVCTTB-UHFFFAOYSA-N 0.000 claims description 5
- UZCWWIUDVDTUBV-UHFFFAOYSA-N 3-hydroxy-2-methoxy-5,6-dimethyl-4-[3-(4-methylthiophen-2-yl)prop-2-enoyl]benzoic acid Chemical compound CC1=C(C(O)=O)C(OC)=C(O)C(C(=O)C=CC=2SC=C(C)C=2)=C1C UZCWWIUDVDTUBV-UHFFFAOYSA-N 0.000 claims description 4
- WFGYKQQMHKGWGK-UHFFFAOYSA-N 4-[3-(4-hexoxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoic acid Chemical compound C(CCCCC)OC1=CC=C(C=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)O)C)OC(C)C)=O WFGYKQQMHKGWGK-UHFFFAOYSA-N 0.000 claims description 4
- NBFJDJPZBRPWGG-UHFFFAOYSA-N 5-[3-(2-hydroxyphenyl)-3-oxoprop-1-enyl]-4-propan-2-ylthiophene-3-carboxylic acid Chemical compound OC1=C(C=CC=C1)C(C=CC=1SC=C(C=1C(C)C)C(=O)O)=O NBFJDJPZBRPWGG-UHFFFAOYSA-N 0.000 claims description 4
- 125000005130 alkyl carbonyl thio group Chemical group 0.000 claims description 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
- 208000026935 allergic disease Diseases 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- VHLOANBRCFGJQF-UHFFFAOYSA-N tert-butyl 2,6-dimethyl-4-[3-(4-methylsulfanylphenyl)-3-oxoprop-1-enyl]-3-propan-2-yloxybenzoate Chemical compound CSC1=CC=C(C=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)OC(C)(C)C)C)OC(C)C)=O VHLOANBRCFGJQF-UHFFFAOYSA-N 0.000 claims description 4
- PQAPZPBWWMAMNQ-UHFFFAOYSA-N tert-butyl 4-[3-(2-methoxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoate Chemical compound COC1=C(C=CC=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)OC(C)(C)C)C)OC(C)C)=O PQAPZPBWWMAMNQ-UHFFFAOYSA-N 0.000 claims description 4
- UVYOKRBWZAUPRA-UHFFFAOYSA-N tert-butyl 4-[3-(4-hexoxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoate Chemical compound C(CCCCC)OC1=CC=C(C=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)OC(C)(C)C)C)OC(C)C)=O UVYOKRBWZAUPRA-UHFFFAOYSA-N 0.000 claims description 4
- UGIDQSSWAJAWFD-UHFFFAOYSA-N 4-[3-(2-hydroxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethoxy-3-propan-2-yloxybenzoic acid Chemical compound OC1=C(C=CC=C1)C(C=CC1=C(C(=C(C(=C1)OC)C(=O)O)OC)OC(C)C)=O UGIDQSSWAJAWFD-UHFFFAOYSA-N 0.000 claims description 3
- SHOKWHLEACINRX-UHFFFAOYSA-N 4-[3-(2-methoxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoic acid Chemical compound COC1=C(C=CC=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)O)C)OC(C)C)=O SHOKWHLEACINRX-UHFFFAOYSA-N 0.000 claims description 3
- JUDMXGILSKKAFL-UHFFFAOYSA-N 4-[3-(3,5-ditert-butyl-4-hydroxyphenyl)prop-2-enoyl]-3-hydroxy-2-methoxy-5,6-dimethylbenzoic acid Chemical compound CC1=C(C(O)=O)C(OC)=C(O)C(C(=O)C=CC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1C JUDMXGILSKKAFL-UHFFFAOYSA-N 0.000 claims description 3
- CFMGACOOXDRGTH-UHFFFAOYSA-N 4-[3-(4-bromophenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoic acid Chemical compound BrC1=CC=C(C=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)O)C)OC(C)C)=O CFMGACOOXDRGTH-UHFFFAOYSA-N 0.000 claims description 3
- DTHFCWZIGVIVMR-UHFFFAOYSA-N 4-[3-(4-chloro-2-hydroxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethoxy-3-propan-2-yloxybenzoic acid Chemical compound OC1=C(C=CC(=C1)Cl)C(C=CC1=C(C(=C(C(=C1)OC)C(=O)O)OC)OC(C)C)=O DTHFCWZIGVIVMR-UHFFFAOYSA-N 0.000 claims description 3
- ABOMYHLRDVSLSH-UHFFFAOYSA-N 5-[3-(4-chloro-2-hydroxyphenyl)-3-oxoprop-1-enyl]-4-propan-2-ylthiophene-3-carboxylic acid Chemical compound ClC1=CC(=C(C=C1)C(C=CC=1SC=C(C=1C(C)C)C(=O)O)=O)O ABOMYHLRDVSLSH-UHFFFAOYSA-N 0.000 claims description 3
- ORCGGRWTEDPBOY-UHFFFAOYSA-N 5-[3-(4-methylthiophen-2-yl)prop-2-enoyl]-4-propan-2-ylthiophene-3-carboxylic acid Chemical compound C(=O)(O)C=1C(=C(SC=1)C(C=CC=1SC=C(C=1)C)=O)C(C)C ORCGGRWTEDPBOY-UHFFFAOYSA-N 0.000 claims description 3
- WLBLYHVNHUXYFK-UHFFFAOYSA-N COC1=C(C)C(C(O)=O)=C(C)C=C1C(=O)C=CC1=CC(C)=CS1 Chemical compound COC1=C(C)C(C(O)=O)=C(C)C=C1C(=O)C=CC1=CC(C)=CS1 WLBLYHVNHUXYFK-UHFFFAOYSA-N 0.000 claims description 3
- OPAXADMAZRWQED-UHFFFAOYSA-N COC1=C(C)C(C(O)=O)=C(C)C=C1C=CC(=O)C1=CC(C)=CS1 Chemical compound COC1=C(C)C(C(O)=O)=C(C)C=C1C=CC(=O)C1=CC(C)=CS1 OPAXADMAZRWQED-UHFFFAOYSA-N 0.000 claims description 3
- QDMONAIGPRKTII-UHFFFAOYSA-N CSc1ccc(cc1)C(=O)C=Cc1cc(C)c(C(=O)OC(C)C)c(C)c1OC(C)C Chemical compound CSc1ccc(cc1)C(=O)C=Cc1cc(C)c(C(=O)OC(C)C)c(C)c1OC(C)C QDMONAIGPRKTII-UHFFFAOYSA-N 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- WJYKWIJJTZJPFR-UHFFFAOYSA-N ethyl 4-[3-(3,5-ditert-butyl-4-hydroxyphenyl)prop-2-enoyl]-3-hydroxy-2-methoxy-5,6-dimethylbenzoate Chemical compound OC1=C(OC)C(C(=O)OCC)=C(C)C(C)=C1C(=O)C=CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 WJYKWIJJTZJPFR-UHFFFAOYSA-N 0.000 claims description 3
- 150000004677 hydrates Chemical class 0.000 claims description 3
- IMNPYBGZLXECCA-UHFFFAOYSA-N propan-2-yl 4-[3-(2-hydroxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoate Chemical compound OC1=C(C=CC=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)OC(C)C)C)OC(C)C)=O IMNPYBGZLXECCA-UHFFFAOYSA-N 0.000 claims description 3
- FQRVOIZHBLCACQ-UHFFFAOYSA-N propan-2-yl 4-[3-(4-chlorophenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoate Chemical compound ClC1=CC=C(C=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)OC(C)C)C)OC(C)C)=O FQRVOIZHBLCACQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 125000000565 sulfonamide group Chemical group 0.000 claims description 3
- UAYFKWJMLFSUQX-UHFFFAOYSA-N tert-butyl 4-[3-(4-bromophenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoate Chemical compound BrC1=CC=C(C=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)OC(C)(C)C)C)OC(C)C)=O UAYFKWJMLFSUQX-UHFFFAOYSA-N 0.000 claims description 3
- NXLNJFKRZXNAOC-UHFFFAOYSA-N tert-butyl 4-[3-(4-chloro-2-methoxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoate Chemical compound COC1=C(C=CC(=C1)Cl)C(C=CC1=C(C(=C(C(=C1)C)C(=O)OC(C)(C)C)C)OC(C)C)=O NXLNJFKRZXNAOC-UHFFFAOYSA-N 0.000 claims description 3
- XGCCDWQJDAEUGP-UHFFFAOYSA-N tert-butyl 4-[3-(4-heptylphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoate Chemical compound C(CCCCCC)C1=CC=C(C=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)OC(C)(C)C)C)OC(C)C)=O XGCCDWQJDAEUGP-UHFFFAOYSA-N 0.000 claims description 3
- ORGWAHMDAYMJSE-UHFFFAOYSA-N 3-hydroxy-4-[3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoyl]-2-methoxy-5,6-dimethylbenzoic acid Chemical compound COC1=C(O)C(OC)=CC(C=CC(=O)C=2C(=C(OC)C(C(O)=O)=C(C)C=2C)O)=C1 ORGWAHMDAYMJSE-UHFFFAOYSA-N 0.000 claims description 2
- KQXBUZUTUYGTNN-UHFFFAOYSA-N 3-hydroxy-4-[3-(4-hydroxy-3,5-dimethylphenyl)prop-2-enoyl]-2-methoxy-5,6-dimethylbenzoic acid Chemical compound CC1=C(C(O)=O)C(OC)=C(O)C(C(=O)C=CC=2C=C(C)C(O)=C(C)C=2)=C1C KQXBUZUTUYGTNN-UHFFFAOYSA-N 0.000 claims description 2
- HRCQDLFWCLASAY-UHFFFAOYSA-N 3-tert-butyl-5-[3-(4-chloro-2-hydroxyphenyl)-3-oxoprop-1-enyl]-2-hydroxy-6-propan-2-ylbenzoic acid Chemical compound OC1=C(C=CC(=C1)Cl)C(C=CC1=C(C(=C(C(=C1)C(C)(C)C)O)C(=O)O)C(C)C)=O HRCQDLFWCLASAY-UHFFFAOYSA-N 0.000 claims description 2
- AVVRYGNYRWAYGY-UHFFFAOYSA-N 4-[3-(2-hydroxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoic acid Chemical compound OC1=C(C=CC=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)O)C)OC(C)C)=O AVVRYGNYRWAYGY-UHFFFAOYSA-N 0.000 claims description 2
- CCEVUTOSCLFOPX-UHFFFAOYSA-N 4-[3-(4-bromo-2-hydroxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoic acid Chemical compound OC1=C(C=CC(=C1)Br)C(C=CC1=C(C(=C(C(=C1)C)C(=O)O)C)OC(C)C)=O CCEVUTOSCLFOPX-UHFFFAOYSA-N 0.000 claims description 2
- FJHGEZHEKOTGPQ-UHFFFAOYSA-N 4-[3-(4-chloro-2-hydroxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoic acid Chemical compound OC1=C(C=CC(=C1)Cl)C(C=CC1=C(C(=C(C(=C1)C)C(=O)O)C)OC(C)C)=O FJHGEZHEKOTGPQ-UHFFFAOYSA-N 0.000 claims description 2
- KTIRWVUQFYPEMT-UHFFFAOYSA-N 4-[3-(4-chloro-2-methoxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoic acid Chemical compound COC1=C(C=CC(=C1)Cl)C(C=CC1=C(C(=C(C(=C1)C)C(=O)O)C)OC(C)C)=O KTIRWVUQFYPEMT-UHFFFAOYSA-N 0.000 claims description 2
- STYJSGCSXWUMLH-UHFFFAOYSA-N 4-[3-(4-chlorophenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoic acid Chemical compound ClC1=CC=C(C=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)O)C)OC(C)C)=O STYJSGCSXWUMLH-UHFFFAOYSA-N 0.000 claims description 2
- YBSIVKSGSCKXIN-UHFFFAOYSA-N 4-[3-(4-heptylphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoic acid Chemical compound C(CCCCCC)C1=CC=C(C=C1)C(C=CC1=C(C(=C(C(=C1)C)C(=O)O)C)OC(C)C)=O YBSIVKSGSCKXIN-UHFFFAOYSA-N 0.000 claims description 2
- LMDUSDRCJKWSCI-UHFFFAOYSA-N 4-[3-(4-hydroxy-3,5-dimethylphenyl)prop-2-enoyl]-3-methoxy-2,6-dimethylbenzoic acid Chemical compound COC1=C(C)C(C(O)=O)=C(C)C=C1C(=O)C=CC1=CC(C)=C(O)C(C)=C1 LMDUSDRCJKWSCI-UHFFFAOYSA-N 0.000 claims description 2
- FCIWMCRVTHHWRO-UHFFFAOYSA-N 5-[3-(4-chloro-2-hydroxyphenyl)-3-oxoprop-1-enyl]-2,3-dihydroxy-4-propan-2-yloxybenzoic acid Chemical compound OC1=C(C=CC(=C1)Cl)C(C=CC1=C(C(=C(C(=C1)C(=O)O)O)O)OC(C)C)=O FCIWMCRVTHHWRO-UHFFFAOYSA-N 0.000 claims description 2
- QJVGPZZIVKVJFT-UHFFFAOYSA-N COc1cc(C=CC(=O)c2ccc(Cl)cc2O)c(OC(C)C)c(OC)c1C(=O)OC(C)C Chemical compound COc1cc(C=CC(=O)c2ccc(Cl)cc2O)c(OC(C)C)c(OC)c1C(=O)OC(C)C QJVGPZZIVKVJFT-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical group O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- VNSXSUDRWQVXQX-UHFFFAOYSA-N propan-2-yl 3-hydroxy-4-[3-(4-hydroxy-3,5-dimethylphenyl)prop-2-enoyl]-2-methoxy-5,6-dimethylbenzoate Chemical compound CC1=C(C(=O)OC(C)C)C(OC)=C(O)C(C(=O)C=CC=2C=C(C)C(O)=C(C)C=2)=C1C VNSXSUDRWQVXQX-UHFFFAOYSA-N 0.000 claims description 2
- OXQGMXQAXUNOPX-UHFFFAOYSA-N propan-2-yl 3-tert-butyl-2-hydroxy-5-[3-(2-hydroxyphenyl)-3-oxoprop-1-enyl]-6-propan-2-ylbenzoate Chemical compound OC1=C(C=CC=C1)C(C=CC1=C(C(=C(C(=C1)C(C)(C)C)O)C(=O)OC(C)C)C(C)C)=O OXQGMXQAXUNOPX-UHFFFAOYSA-N 0.000 claims description 2
- XIHQQHVYKPBBPG-UHFFFAOYSA-N propan-2-yl 3-tert-butyl-2-hydroxy-5-[3-(2-hydroxyphenyl)-3-oxoprop-1-enyl]-6-propan-2-yloxybenzoate Chemical compound OC1=C(C=CC=C1)C(C=CC1=C(C(=C(C(=C1)C(C)(C)C)O)C(=O)OC(C)C)OC(C)C)=O XIHQQHVYKPBBPG-UHFFFAOYSA-N 0.000 claims description 2
- DTLZNGNJVDDLRO-UHFFFAOYSA-N propan-2-yl 3-tert-butyl-5-[3-(4-chloro-2-hydroxyphenyl)-3-oxoprop-1-enyl]-2-hydroxy-6-propan-2-ylbenzoate Chemical compound OC1=C(C=CC(=C1)Cl)C(C=CC1=C(C(=C(C(=C1)C(C)(C)C)O)C(=O)OC(C)C)C(C)C)=O DTLZNGNJVDDLRO-UHFFFAOYSA-N 0.000 claims description 2
- RWTYIQUKHSQDBG-UHFFFAOYSA-N propan-2-yl 3-tert-butyl-5-[3-(4-chloro-2-hydroxyphenyl)-3-oxoprop-1-enyl]-2-hydroxy-6-propan-2-yloxybenzoate Chemical compound OC1=C(C=CC(=C1)Cl)C(C=CC1=C(C(=C(C(=C1)C(C)(C)C)O)C(=O)OC(C)C)OC(C)C)=O RWTYIQUKHSQDBG-UHFFFAOYSA-N 0.000 claims description 2
- FVGWOYHTPSYJAT-UHFFFAOYSA-N propan-2-yl 4-[3-(2-hydroxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethoxy-3-propan-2-yloxybenzoate Chemical compound OC1=C(C=CC=C1)C(C=CC1=C(C(=C(C(=C1)OC)C(=O)OC(C)C)OC)OC(C)C)=O FVGWOYHTPSYJAT-UHFFFAOYSA-N 0.000 claims description 2
- MDFBNCMYCZWGII-UHFFFAOYSA-N propan-2-yl 4-[3-(4-chloro-2-hydroxyphenyl)-3-oxoprop-1-enyl]-2,6-dimethyl-3-propan-2-yloxybenzoate Chemical compound CC(C)OC(=O)c1c(C)cc(C=CC(=O)c2ccc(Cl)cc2O)c(OC(C)C)c1C MDFBNCMYCZWGII-UHFFFAOYSA-N 0.000 claims description 2
- VOAJFPABBOWCFW-UHFFFAOYSA-N propan-2-yl 5-[3-(2-hydroxyphenyl)-3-oxoprop-1-enyl]-4-propan-2-ylthiophene-3-carboxylate Chemical compound OC1=C(C=CC=C1)C(C=CC=1SC=C(C=1C(C)C)C(=O)OC(C)C)=O VOAJFPABBOWCFW-UHFFFAOYSA-N 0.000 claims description 2
- ZHDCBZKFECJECR-UHFFFAOYSA-N 3-tert-butyl-2-hydroxy-5-[3-(2-hydroxyphenyl)-3-oxoprop-1-enyl]-6-propan-2-yloxybenzoic acid Chemical compound OC1=C(C=CC=C1)C(C=CC1=C(C(=C(C(=C1)C(C)(C)C)O)C(=O)O)OC(C)C)=O ZHDCBZKFECJECR-UHFFFAOYSA-N 0.000 claims 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 235000012054 meals Nutrition 0.000 claims 2
- GIQPSSZMIZARDW-UHFFFAOYSA-N 2-phenylthiochromen-4-one Chemical compound S1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 GIQPSSZMIZARDW-UHFFFAOYSA-N 0.000 claims 1
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Abstract
Description
화합물 | 농도 | 유도인자 |
Cp3 | 10μM 30μM 100μM | 30.12 27.27 25.84 |
Cp4 | 10μM 30μM 100μM | 3.99 22.15 61.07 |
Cp7 | 10μM 30μM 100μM | 36.48 50.37 37.84 |
Cp8 | 10μM 30μM 100μM | 0.62 1.27 9.98 |
Cp9 | 10μM 30μM 100μM | 2.11 5.00 28.19 |
화합물 | 농도 | 유도인자 |
Cp11 | 1μM 10μM 100μM | 1.20 1.39 10.19 |
Cp12 | 1μM 10μM 100μM | 1.12 8.45 22.54 |
Cp13 | 1μM 10μM 100μM | 1.20 1.10 1.5 |
Cp14 | 1μM 10μM 100μM | 1.25 1.36 1.38 |
Cp17 | 1μM 10μM 100μM | 79.76 85.69 13.80 |
화합물 | 농도 | 유도인자 |
Cp19 | 1μM 10μM 100μM | 1.20 15.62 0.07 |
Cp20 | 1μM 10μM 100μM | 21.50 53.45 1.22 |
Cp21 | 1μM 10μM 100μM | 0.78 1.10 22.80 |
Cp22 | 1μM 10μM 100μM | 2.40 49.49 2.73 |
화합물 | 농도 | 유도인자 |
Cp23 | 1μM 10μM 100μM | 1.55 3.67 0.12 |
Cp24 | 1μM 10μM 100μM | 2.06 11.62 0.00 |
Cp25 | 1μM 10μM 100μM | 13.48 21.03 7.01 |
Cp26 | 1μM 10μM 100μM | 1.75 7.85 1.08 |
Cp29 | 1μM 10μM 100μM | 28.36 25.26 0.27 |
화합물 | 농도 | 유도인자 |
Cp31 | 1μM 10μM 100μM | 3.77 15.52 1.21 |
Cp33 | 1μM 10μM 100μM | 22.05 44.52 77.62 |
화합물 | 농도 | 유도인자 |
Cp37 | 1μM 10μM 100μM | 24.55 27.83 0.02 |
Cp38 | 1μM 10μM 100μM | 14.70 22.22 0.311 |
Cp41 | 1μM 10μM 100μM | 34.61 31.18 3.39 |
화합물 | 유도인자 | |
Cp17 | 1μM 10μM 100μM | 15.37 24.92 6.13 |
Cp33 | 1μM 10μM 100μM | 15.65 33.90 45.58 |
Cp29 | 1μM 10μM 100μM | 17.05 33.89 0.01 |
Claims (37)
- 약제학적으로 허용가능한 지지체내에 하기 화학식 1로 표현되는 적어도 하나의 치환된 1,3-디페닐프로프-2-엔-1-온 유도체, 이의 광학이성체 및 기하 이성체, 라세미체, 토우토머, 염, 수화물 또는 이들의 혼합물을 포함하는, 죽상경화증, 알러지, 천식, 습진, 건선, 소양증, 알쯔하이머 질환, 파킨슨 질환, 당뇨, 비만, 및 암으로 이루어진 군에서 선택되는 질환을 치료 또는 예방하기 위한 약제학적 조성물.[화학식 1](식중,X1은 할로겐 또는 -R1 그룹 또는 식 -G1-R1에 해당하는 그룹을 나타내고,X2는 수소원자, 티오니트로소 그룹, 하이드록시 그룹, 알킬카보닐옥시 그룹, 비치환된 알킬옥시 그룹, 티올 그룹, 알킬티오 그룹 또는 알킬카보닐티오 그룹을 나타내고, X2는 또한 2-페닐-4H-1-벤조피란-4-온 형태의 유도체 또는 2-페닐-4H-1-벤조티오피란-4-온 형태의 유도체를 형성하기 위해 프로펜 사슬의 3번 탄소에 결합된 산소 또는 황 원자일 수 있고,X3는 -R3 그룹 또는 식 -G3-R3에 해당하는 그룹을 나타내고,X4는 할로겐, 티오니트로소 그룹, -R4 그룹 또는 식 -G4-R4에 해당하는 그룹을 나타내고,X5는 -R5 그룹 또는 식 -G5-R5에 해당하는 그룹을 나타내고,X6은 산소원자이고,R1, R3, R4, R5는, 서로 상이하거나 동일하게, 수소원자, 또는 이하에서 정의되는 그룹 1 또는 그룹 2의 일부인 치환기로 치환되거나 치환되지 않은 알킬 그룹이고,G1, G3, G4, G5는, 서로 상이하거나 동일하게, 산소원자 또는 황원자를 나타내고,상기 X1, X3, X4 또는 X5 그룹 중 적어도 하나는 식 -G-R에 해당하고, G는 황 원자이며,상기 R1, R3, R4 또는 R5 그룹 중 적어도 하나는, 그룹 1 또는 그룹 2로부터의 적어도 하나의 치환기를 함유하는 알킬 그룹 형태로 존재하고, 상기 알킬 그룹은 고리에 직접 결합되거나 식 -GR에 따라 그룹 G와 연결되어 있고,상기 그룹 1로부터의 치환기는 식 -COOR6에 해당하는 카복시 그룹 및 식 -CONR6R7에 해당하는 카바모일 그룹으로 구성된 그룹으로부터 선택되고,상기 그룹 2로부터의 치환기는 설폰산(-SO3H) 및 식 -SO2NR6R7에 해당하는 설폰아미드 그룹으로 구성된 그룹으로부터 선택되고,상기 R6 및 R7은, 서로 상이 하거나 동일하게, 수소원자 또는 타입 1 또는 타입 2의 적어도 하나의 그룹에 의해 치환될 수 있는 알킬 그룹이며,단, 화학식 1로 표현되는 화합물 중 X2가 수소원자를 나타내고 X1이 -G1R1을 나타내며 여기서 G1은 산소원자를 나타내고 R1은 CH2COOH를 나타내는 화합물은 제외한다.)
- 약제학적으로 허용가능한 지지체내에 하기 화학식 1로 표현되는 적어도 하나의 치환된 1,3-디페닐프로프-2-엔-1-온 유도체, 이의 광학이성체 및 기하 이성체, 라세미체, 토우토머, 염, 수화물 또는 이들의 혼합물을 포함하는, 죽상경화증, 알러지, 천식, 습진, 건선, 소양증, 알쯔하이머 질환, 파킨슨 질환, 당뇨, 비만, 및 암으로 이루어진 군에서 선택되는 질환을 치료 또는 예방하기 위한 약제학적 조성물.[화학식 1](식중,X1은 할로겐 또는 -R1 그룹 또는 식 -G1-R1에 해당하는 그룹을 나타내고,X2는 수소원자, 티오니트로소 그룹, 하이드록시 그룹, 알킬카보닐옥시 그룹, 비치환된 알킬옥시 그룹, 티올 그룹, 알킬티오 그룹 또는 알킬카보닐티오 그룹을 나타내고, X2는 또한 2-페닐-4H-1-벤조티오피란-4-온 형태의 유도체를 형성하기 위해 프로펜 사슬의 3번 탄소에 결합된 황 원자일 수 있고,X3는 -R3 그룹 또는 식 -G3-R3에 해당하는 그룹을 나타내고,X4는 할로겐, 티오니트로소 그룹, -R4 그룹 또는 식 -G4-R4에 해당하는 그룹을 나타내고,X5는 -R5 그룹 또는 식 -G5-R5에 해당하는 그룹을 나타내고,X6은 산소원자이고,R1, R3, R4, R5는, 서로 상이하거나 동일하게, 수소원자, 또는 이하에서 정의되는 그룹 1 또는 그룹 2의 일부인 치환기로 치환되거나 치환되지 않은 알킬 그룹이고,G1, G3, G4, G5는, 서로 상이하거나 동일하게, 산소원자 또는 황원자를 나타내고,상기 X1, X3, X4 또는 X5 그룹중 적어도 하나는 식 -G-R에 해당하고, G는 산소원자 또는 황 원자이며,상기 X3, X4 또는 X5 그룹 중 어느 것도 수소원자가 아니며,상기 R1, R3, R4 또는 R5 그룹중 적어도 하나는, 그룹 1 또는 그룹 2로부터의 적어도 하나의 치환기를 함유하는 알킬 그룹 형태로 존재하고, 상기 알킬 그룹은 고리에 직접 결합되거나 식 -GR에 따라 그룹 G와 연결되어 있고,상기 그룹 1로부터의 치환기는 식 -COOR6에 해당하는 카복시 그룹 및 식 -CONR6R7에 해당하는 카바모일 그룹으로 구성된 그룹으로부터 선택되고,상기 그룹 2로부터의 치환기는 설폰산(-SO3H) 및 식 -SO2NR6R7에 해당하는 설폰아미드 그룹으로 구성된 그룹으로부터 선택되고,상기 R6 및 R7은, 서로 상이하거나 동일하게, 수소원자 또는 타입 1 또는 타입 2의 적어도 하나의 그룹에 의해 치환될 수 있는 알킬 그룹이며,단, 화학식 1로 표현되는 화합물 중 X2가 수소원자를 나타내고 X1이 -G1R1을 나타내며 여기서 G1은 산소원자를 나타내고 R1은 CH2COOH를 나타내는 화합물은 제외한다.)
- 제1항 또는 제2항에 있어서, 유도체가 시스 또는 트랜스 구조 또는 이의 혼합물인 것을 특징으로 하는 조성물.
- 제1항에 있어서, X3, X4 및 X5 그룹중 어느 것도 수소원자가 아닌 것을 특징으로 하는 조성물.
- 제1항에 있어서, X3, X4 및 X5 그룹중 하나 또는 두개가 수소원자인 것을 특징으로 하는 조성물.
- 제1항 또는 제2항에 있어서, G1 그룹 및 G4 그룹이 모두 황원자인 것을 특징으로 하는 조성물.
- 제1항 또는 제2항에 있어서, X2가 수소원자, 티오니트로소 그룹 또는 하이드록시 그룹 또는 알킬옥시 또는 티올 그룹 또는 알킬티오 그룹인 것을 특징으로 하는 조성물.
- 제1항 또는 제2항에 있어서, X4가 티오니트로소 그룹 또는 -R4 그룹 또는 식 -G4-R4에 해당하는 그룹이고, X2가 티오니트로소 그룹 또는 하이드록시 그룹 또는 알킬옥시 그룹 또는 티올 그룹 또는 알킬티오 그룹이며, G4 및 R4는 제1항 또는 제2항에 정의된 바와 같은 것을 특징으로 하는 조성물.
- 제1항 또는 제2항에 있어서, X1이 -R1 그룹 또는 식 -G1-R1에 해당하는 그룹이고, R1은 그룹 1의 일부인 치환기로 치환된 알킬 그룹이며, G1 및 그룹 1로부터의 치환기는 제1항 또는 제2항에 정의된 바와 같은 것을 특징으로 하는 조성물.
- 제1항 또는 제2항에 있어서, X1이 -G1-R1 그룹이고, G1 및 R1은 제1항 또는 제2항에 정의된 바와 같은 것을 특징으로 하는 조성물.
- 제1항 또는 제2항에 있어서, X1이 -G1-R1 그룹이고, G1이 산소원자이며, R1은 제1항 또는 제2항에 정의된 바와 같은 것을 특징으로 하는 조성물.
- 제1항 또는 제2항에 있어서, X1이 -R1 그룹 또는 식 -G1-R1에 해당하는 그룹이고, R1은 그룹 2의 일부인 치환기로 치환된 알킬 그룹이며, G1 및 그룹 2로부터의 치환기는 제1항 또는 제2항에 정의된 바와 같은 것을 특징으로 하는 조성물.
- 제1항 또는 제2항에 있어서, X3이 -R3 그룹 또는 식 -G3-R3에 해당하는 그룹이고, R3은 그룹 1의 일부인 치환기로 치환된 알킬 그룹이며, 상기 G3 및 그룹 1 로부터의 치환기는 제1항 또는 제2항에 정의된 바와 같은 것을 특징으로 하는 조성물.
- 제1항 또는 제2항에 있어서, X3이 -R3 그룹 또는 식 -G3-R3에 해당하는 그룹이고, R3은 그룹 2의 일부인 치환기로 치환된 알킬 그룹이며, G3 및 그룹 2로부터의 치환기는 제1항 또는 제2항에 정의된 바와 같은 것을 특징으로 하는 조성물.
- 제1항 또는 제2항에 있어서, X4가 -R4 그룹 또는 식 -G4-R4에 해당하는 그룹이고, R4는 그룹 1의 일부인 치환기로 치환된 알킬 그룹이며, G4 및 그룹 1로부터의 치환기는 제1항 또는 제2항에 정의된 바와 같은 것을 특징으로 하는 조성물.
- 제1항 또는 제2항에 있어서, X4가 -G4-R4 그룹이고, G4 및 R4는 제1항 또는 제2항에 정의된 바와 같은 것을 특징으로 하는 조성물.
- 제1항 또는 제2항에 있어서, X4가 -G4-R4 그룹이고, G4가 산소원자이며, R4는 제1항 또는 제2항에 정의된 바와 같은 것을 특징으로 하는 조성물.
- 제1항 또는 제2항에 있어서, X4가 -G4-R4 그룹이고, G4는 산소원자이며, X3 또는 X5는 한편으로는 각각 R3 또는 -G3-R3이고 다른 한편으로는 각각 R5 또는 -G5-R5이며, R3 및 R5는 그룹 1로부터의 치환기를 갖는 알킬 그룹이고, R4, G3, G5 및 그룹 1로부터의 치환기는 제1항 또는 제2항에 정의된 바와 같은 것을 특징으로 하는 조성물.
- 제1항 또는 제2항에 있어서, X4가 -R4 그룹 또는 식 -G4-R4에 해당하는 그룹이고 상기 R4는 그룹 2의 일부인 치환기로 치환된 알킬 그룹이고, G4 및 그룹 2로부터의 치환기는 제1항 또는 제2항에 정의된 바와 같은 것을 특징으로 하는 조성물.
- 제1항 또는 제2항에 있어서, X1이 할로겐인 것을 특징으로 하는 조성물.
- 제1항 또는 제2항에 있어서, X1, X3, X4 또는 X5가 OC(CH3)2COOR6이고, R6는 제1항 또는 제2항에 정의된 바와 같은 것을 특징으로 하는 조성물.
- 제1항 또는 제2항에 있어서, X1, X3, X4 또는 X5가 SC(CH3)2COOR6이고, R6는 제1항 또는 제2항에 정의된 바와 같은 것을 특징으로 하는 조성물.
- 제1항 또는 제2항에 있어서, 상기 유도체는 하기 화합물들로 구성된 군에서 선택된 것을 특징으로 하는 조성물:1-[2-하이드록시-4-카복시디메틸메틸옥시페닐]-3-[3,5-디-t-부틸-4-하이드록시페닐]프로프-2-엔-1-온,1-[2-하이드록시-4-에톡시카보닐디메틸메틸옥시페닐]-3-[3,5-디-t-부틸-4-하이드록시페닐]프로프-2-엔-1-온,1-[2-하이드록시-4-이소프로필옥시카보닐디메틸메틸옥시페닐]-3-[3,5-디-t-부틸-4-하이드록시페닐]프로프-2-엔-1-온,1-[2-하이드록시페닐]-3-[3-카복시디메틸메틸옥시-4-하이드록시-5-t-부틸페닐]프로프-2-엔-1-온,1-[2-하이드록시페닐]-3-[3-이소프로필옥시카보닐디메틸메틸옥시-4-하이드록시-5-t-부틸페닐]프로프-2-엔-1-온,1-[2-하이드록시-4-클로로페닐]-3-[3-카복시디메틸메틸옥시-4-하이드록시-5-t-부틸페닐]프로프-2-엔-1-온,1-[2-하이드록시-4-클로로페닐]-3-[3-이소프로필옥시카보닐디메틸메틸옥시-4-하이드록시-5-t-부틸페닐]프로프-2-엔-1-온,1-[2-하이드록시페닐]-3-[3-카복시디메틸메틸옥시-4-하이드록시-5-t-부틸페닐]프로프-2-엔-1-온,1-[2-하이드록시페닐]-3-[3-이소프로필옥시카보닐디메틸메틸-4-하이드록시-5-t-부틸페닐]프로프-2-엔-1-온,1-[2-하이드록시-4-클로로페닐]-3-[3-카복시디메틸메틸-4-하이드록시-5-t-부틸페닐]프로프-2-엔-1-온,1-[2-하이드록시-4-클로로페닐]-3-[3-이소프로필옥시카보닐디메틸메틸-4-하이드록시-5-t-부틸페닐]프로프-2-엔-1-온,1-[2-하이드록시-4-클로로페닐]-3-[3,5-디메톡시-4-카복시디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[2-하이드록시-4-클로로페닐]-3-[3,5-디메톡시-4-이소프로필옥시카보닐디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[2-하이드록시페닐]-3-[3,5-디메톡시-4-카복시디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[2-하이드록시페닐]-3-[3,5-디메톡시-4-이소프로필옥시카보닐디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[2-하이드록시-4-카복시디메틸메틸옥시페닐]-3-[3,5-디메톡시-4-하이드록시페닐]프로프-2-엔-1-온,1-[2-하이드록시-4-이소프로필옥시카보닐디메틸메틸옥시페닐]-3-[3,5-디메톡시-4-하이드록시페닐]프로프-2-엔-1-온,1-[2-하이드록시-4-클로로페닐]-3-[3,4-디하이드록시-5-카복시디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[2-하이드록시-4-클로로페닐]-3-[3,4-디하이드록시-5-이소프로필옥시카보닐디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[2-하이드록시-4-카복시디메틸메틸옥시페닐]-3-[3,5-디메틸-4-하이드록시페닐]프로프-2-엔-1-온,1-[2-하이드록시-4-이소프로필옥시카보닐디메틸메틸옥시페닐]-3-[3,5-디메틸-4-하이드록시페닐]프로프-2-엔-1-온,1-[2-하이드록시-4-클로로페닐]-3-[3,5-디메틸-4-카복시디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[2-하이드록시-4-클로로페닐]-3-[3,5-디메틸-4-이소프로필옥시카보닐디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[2-하이드록시페닐]-3-[3,5-디메틸-4-카복시디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[2-하이드록시페닐]-3-[3,5-디메틸-4-이소프로필옥시카보닐디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[2-하이드록시페닐]-3-[4-카복시디메틸메틸티오페닐]프로프-2-엔-1-온,1-[2-하이드록시페닐]-3-[4-이소프로필옥시카보닐디메틸메틸티오페닐]프로프-2-엔-1-온,1-[2-하이드록시-4-카복시디메틸메틸옥시페닐]-3-[4-메틸티오페닐]프로프-2-엔-1-온,1-[4-클로로페닐]-3-[3,5-디메틸-4-t-부틸옥시카보닐디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[4-클로로페닐]-3-[3,5-디메틸-4-이소프로필옥시카보닐디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[4-클로로페닐]-3-[3,5-디메틸-4-카복시디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[4-클로로-2-하이드록시페닐]-3-[4-카복시디메틸메틸티오페닐]프로프-2-엔-1-온,1-[4-카복시디메틸메틸옥시페닐]-3-[3,5-디메틸-4-하이드록시페닐]프로프-2-엔-1-온,1-[4-메틸티오페닐]-3-[4-카복시디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[4-카복시디메틸메틸티오페닐]-3-[4-메틸티오페닐]프로프-2-엔-1-온,1-[2-하이드록시-4-브로모페닐]-3-[3,5-디메틸-4-카복시디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[4-카복시디메틸메틸옥시페닐]-3-[4-메틸티오페닐]프로프-2-엔-1-온,1-[4-메틸티오페닐]-3-[3,5-디메틸-4-t-부틸옥시카보닐디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[4-메틸티오페닐]-3-[3,5-디메틸-4-이소프로필옥시카보닐디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[4-메틸티오페닐]-3-[3,5-디메틸-4-카복시디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[2-메톡시페닐]-3-[3,5-디메틸-4-t-부틸옥시카보닐디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[2-메톡시페닐]-3-[3,5-디메틸-4-카복시디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[4-헥실옥시페닐]-3-[3,5-디메틸-4-t-부틸옥시카보닐디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[4-헥실옥시페닐]-3-[3,5-디메틸-4-카복시디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[2-메틸옥시-4-클로로페닐]-3-[3,5-디메틸-4-t-부틸옥시카보닐디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[2-메틸옥시-4-클로로페닐]-3-[3,5-디메틸-4-카복시디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[4-헵틸페닐]-3-[3,5-디메틸-4-t-부틸옥시카보닐디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[4-헵틸페닐]-3-[3,5-디메틸-4-카복시디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[4-브로모페닐]-3-[3,5-디메틸-4-t-부틸옥시카보닐디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[4-브로모페닐]-3-[3,5-디메틸-4-카복시디메틸메틸옥시페닐]프로프-2-엔-1-온.
- 제1항 또는 제2항에 있어서, 상기 유도체는 하기 화합물들로 구성된 군에서 선택된 것을 특징으로 하는 조성물:1-[4-메틸티오페닐]-3-[3,5-디메틸-4-카복시디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[4-헥실옥시페닐]-3-[3,5-디메틸-4-카복시디메틸메틸옥시페닐]프로프-2-엔-1-온,1-[4-브로모페닐]-3-[3,5-디메틸-4-카복시디메틸메틸옥시페닐]프로프-2-엔-1-온.
- 제1항 또는 제2항에 있어서, 상기 유도체는 1-[4-메틸티오페닐]-3-[3,5-디메틸-4-카복시디메틸메틸옥시페닐]프로프-2-엔-1-온인 것을 특징으로 하는 조성물.
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FR0208570A FR2841784B1 (fr) | 2002-07-08 | 2002-07-08 | Composition a base de derives de 1,3-diphenylprop-2en-1-one substitues, preparation et utilisations |
FR02/08570 | 2002-07-08 |
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KR20050019818A KR20050019818A (ko) | 2005-03-03 |
KR100947907B1 true KR100947907B1 (ko) | 2010-03-17 |
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US (3) | US7632870B2 (ko) |
EP (1) | EP1519908B1 (ko) |
JP (1) | JP4907083B2 (ko) |
KR (1) | KR100947907B1 (ko) |
CN (1) | CN1688532B (ko) |
AT (1) | ATE364588T1 (ko) |
AU (1) | AU2003264699B2 (ko) |
BR (1) | BRPI0312399B8 (ko) |
CA (1) | CA2490993C (ko) |
CY (1) | CY1108051T1 (ko) |
DE (1) | DE60314420T2 (ko) |
DK (1) | DK1519908T3 (ko) |
EA (1) | EA012699B1 (ko) |
ES (1) | ES2287529T3 (ko) |
FR (1) | FR2841784B1 (ko) |
IL (1) | IL165454A (ko) |
MX (1) | MXPA05000425A (ko) |
NO (1) | NO334650B1 (ko) |
NZ (1) | NZ538052A (ko) |
PL (1) | PL207707B1 (ko) |
PT (1) | PT1519908E (ko) |
SI (1) | SI1519908T1 (ko) |
WO (1) | WO2004005243A2 (ko) |
ZA (1) | ZA200501081B (ko) |
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FR2841900B1 (fr) | 2002-07-08 | 2007-03-02 | Genfit S A | Nouveaux derives de 1,3-diphenylprop-2-en-1-one substitues, preparation et utilisations |
FR2841784B1 (fr) | 2002-07-08 | 2007-03-02 | Composition a base de derives de 1,3-diphenylprop-2en-1-one substitues, preparation et utilisations | |
WO2005073184A1 (fr) * | 2004-01-08 | 2005-08-11 | Genfit | Composes derives de 1,3-diphenylprop-2-en-1-one, preparation et utilisations |
EP1856085B1 (en) | 2005-03-11 | 2015-07-08 | Howard Florey Institute Pty Ltd | Flavonoid compounds and uses thereof |
HUE039731T2 (hu) * | 2009-11-26 | 2019-01-28 | Genfit | l,3-difenilprop-2-én-l-on-származékok alkalmazása májbetegségek kezelésére |
WO2011080276A1 (en) | 2009-12-29 | 2011-07-07 | Genfit | Pharmaceutical combinations comprising a dpp-4 inhibitor and a 1,3-diphenylprop-2-en-1-one derivative |
MX2013000391A (es) | 2010-07-12 | 2013-03-08 | Hoffmann La Roche | 1-hidroxiimino-3-fenil-propanos. |
KR20140054066A (ko) | 2011-07-15 | 2014-05-08 | 뉴서트 사이언시스, 인크. | 대사 경로 조절을 위한 조성물 및 방법 |
CA2851062A1 (en) * | 2011-10-26 | 2013-05-02 | F. Hoffmann-La Roche Ag | 1-cycloalkyl- or 1-heterocyclyl-hydroxyimino-3-phenyl-propanes |
US9198454B2 (en) | 2012-03-08 | 2015-12-01 | Nusirt Sciences, Inc. | Compositions, methods, and kits for regulating energy metabolism |
SG10201709195TA (en) | 2012-11-13 | 2017-12-28 | Nusirt Sciences Inc | Compositions and methods for increasing energy metabolism |
TR201819042T4 (tr) * | 2013-01-18 | 2019-01-21 | Genfit | Fibrozis ve kanserlerin tedavisine yönelik yöntemler. |
JP6550370B2 (ja) | 2013-03-15 | 2019-07-24 | ニューサート サイエンシーズ, インコーポレイテッド | 脂質レベルを低下させるロイシンおよびニコチン酸 |
CA2939833A1 (en) | 2014-02-27 | 2015-09-03 | Nusirt Sciences, Inc. | Compositions and methods for the reduction or prevention of hepatic steatosis |
EP3416629A4 (en) | 2016-02-16 | 2019-08-07 | CoNCERT Pharmaceuticals, Inc. | DEUTERATED GFT-505 |
BR112018069560A2 (pt) * | 2016-03-30 | 2019-01-29 | Genfit | diagnóstico não-invasivo de esteato-hepatite não alcoólica |
KR102598289B1 (ko) * | 2016-04-16 | 2023-11-06 | 유니버시티 오브 플로리다 리서치 파운데이션, 인코포레이티드 | 바큘로바이러스 시스템-생산된 재조합 아데노-연관 바이러스의 생물학적 효력을 증진시키는 방법 |
CN108658908B (zh) * | 2017-07-31 | 2019-05-10 | 广州必贝特医药技术有限公司 | 1,3-二取代烯酮类化合物及其应用 |
CN109316601B (zh) * | 2017-07-31 | 2021-11-09 | 武汉朗来科技发展有限公司 | 药物组合物及其用途 |
WO2019105234A1 (zh) | 2017-11-30 | 2019-06-06 | 四川科伦博泰生物医药股份有限公司 | 芳香族化合物及其药物组合物和用途 |
WO2020025789A1 (en) | 2018-08-03 | 2020-02-06 | Genfit | Elafibranor salts |
US11634387B2 (en) | 2019-09-26 | 2023-04-25 | Abionyx Pharma Sa | Compounds useful for treating liver diseases |
AU2021219286A1 (en) | 2020-02-10 | 2022-09-22 | Genfit | Polymorphs of elafibranor |
WO2024029639A1 (ko) * | 2022-08-02 | 2024-02-08 | 제이투에이치바이오텍 주식회사 | 3성분 프로드럭, 이의 약학적 조성물 및 의약 용도 |
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