KR101416262B1 - 치환된 1, 3-디페닐프로판 유도체, 그 제조 및 용도 - Google Patents
치환된 1, 3-디페닐프로판 유도체, 그 제조 및 용도 Download PDFInfo
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- KR101416262B1 KR101416262B1 KR1020097001319A KR20097001319A KR101416262B1 KR 101416262 B1 KR101416262 B1 KR 101416262B1 KR 1020097001319 A KR1020097001319 A KR 1020097001319A KR 20097001319 A KR20097001319 A KR 20097001319A KR 101416262 B1 KR101416262 B1 KR 101416262B1
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- Prior art keywords
- phenyl
- phenoxy
- dimethyl
- group
- propyl
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- VEAFKIYNHVBNIP-UHFFFAOYSA-N 1,3-Diphenylpropane Chemical class C=1C=CC=CC=1CCCC1=CC=CC=C1 VEAFKIYNHVBNIP-UHFFFAOYSA-N 0.000 title abstract description 4
- 238000002360 preparation method Methods 0.000 title description 2
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- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims description 211
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 55
- 125000000217 alkyl group Chemical group 0.000 claims description 43
- 238000011282 treatment Methods 0.000 claims description 43
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 37
- 150000002632 lipids Chemical class 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 31
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
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- 125000003118 aryl group Chemical group 0.000 claims description 9
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- VXOSWPMZFYUBCM-UHFFFAOYSA-N 2-[4-[3-hydroxy-3-(4-methylsulfanylphenyl)propyl]-2,6-dimethylphenoxy]-2-methylpropanoic acid Chemical compound C1=CC(SC)=CC=C1C(O)CCC1=CC(C)=C(OC(C)(C)C(O)=O)C(C)=C1 VXOSWPMZFYUBCM-UHFFFAOYSA-N 0.000 claims description 5
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- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 4
- GJQQFDFMSNAWEF-UHFFFAOYSA-N 2-[2,6-dimethyl-4-[3-(4-methylsulfanylphenyl)-3-oxopropyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(SC)=CC=C1C(=O)CCC1=CC(C)=C(OC(C)(C)C(O)=O)C(C)=C1 GJQQFDFMSNAWEF-UHFFFAOYSA-N 0.000 claims description 3
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- XTPVNKBGUZCGBZ-UHFFFAOYSA-N 2-[2,6-dimethyl-4-[3-(4-methylsulfanylphenyl)-3-propan-2-yloxypropyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(SC)=CC=C1C(OC(C)C)CCC1=CC(C)=C(OC(C)(C)C(O)=O)C(C)=C1 XTPVNKBGUZCGBZ-UHFFFAOYSA-N 0.000 claims 1
- TXHGJEWRWMKOFJ-UHFFFAOYSA-N 2-[4-[3-(2-cyclohexylethoxy)-3-(4-methylsulfanylphenyl)propyl]-2,6-dimethylphenoxy]-2-methylpropanoic acid Chemical compound C1=CC(SC)=CC=C1C(OCCC1CCCCC1)CCC1=CC(C)=C(OC(C)(C)C(O)=O)C(C)=C1 TXHGJEWRWMKOFJ-UHFFFAOYSA-N 0.000 claims 1
- PXCDVTXFFMOUAC-UHFFFAOYSA-N 2-[4-[3-(4-methoxyphenyl)-3-oxopropyl]-2,6-dimethylphenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OC)=CC=C1C(=O)CCC1=CC(C)=C(OC(C)(C)C(O)=O)C(C)=C1 PXCDVTXFFMOUAC-UHFFFAOYSA-N 0.000 claims 1
- AHHHPKNHHMRZNK-UHFFFAOYSA-N 2-[4-[3-(cyclohexylmethoxy)-3-(4-methylsulfanylphenyl)propyl]-2,6-dimethylphenoxy]-2-methylpropanoic acid Chemical compound C1=CC(SC)=CC=C1C(OCC1CCCCC1)CCC1=CC(C)=C(OC(C)(C)C(O)=O)C(C)=C1 AHHHPKNHHMRZNK-UHFFFAOYSA-N 0.000 claims 1
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- VUATYSBCAZCBKH-UHFFFAOYSA-N 2-[4-[3-ethoxy-3-(4-methylsulfanylphenyl)propyl]-2,6-dimethylphenoxy]-2-methylpropanoic acid Chemical compound C=1C=C(SC)C=CC=1C(OCC)CCC1=CC(C)=C(OC(C)(C)C(O)=O)C(C)=C1 VUATYSBCAZCBKH-UHFFFAOYSA-N 0.000 claims 1
- IKBKKKSXBXMPEC-UHFFFAOYSA-N 2-[4-[3-hydroxy-3-(4-propoxyphenyl)propyl]-2,6-dimethylphenoxy]-2-methylpropanoic acid Chemical compound C1=CC(OCCC)=CC=C1C(O)CCC1=CC(C)=C(OC(C)(C)C(O)=O)C(C)=C1 IKBKKKSXBXMPEC-UHFFFAOYSA-N 0.000 claims 1
- UNMLECSVNTUTJZ-UHFFFAOYSA-N 2-[4-[3-hydroxyimino-3-(4-methylsulfanylphenyl)propyl]-2,6-dimethylphenoxy]-2-methylpropanoic acid Chemical compound C1=CC(SC)=CC=C1C(=NO)CCC1=CC(C)=C(OC(C)(C)C(O)=O)C(C)=C1 UNMLECSVNTUTJZ-UHFFFAOYSA-N 0.000 claims 1
- CLRFCWYNECTCNX-UHFFFAOYSA-N 2-[4-[3-methoxy-3-(4-methylsulfanylphenyl)propyl]-2,6-dimethylphenoxy]-2-methylpropanoic acid Chemical compound C=1C=C(SC)C=CC=1C(OC)CCC1=CC(C)=C(OC(C)(C)C(O)=O)C(C)=C1 CLRFCWYNECTCNX-UHFFFAOYSA-N 0.000 claims 1
- UKYBLMLJJJCLFP-UHFFFAOYSA-N 2-[4-[3-methoxyimino-3-(4-methylsulfanylphenyl)propyl]-2,6-dimethylphenoxy]-2-methylpropanoic acid Chemical compound C=1C=C(SC)C=CC=1C(=NOC)CCC1=CC(C)=C(OC(C)(C)C(O)=O)C(C)=C1 UKYBLMLJJJCLFP-UHFFFAOYSA-N 0.000 claims 1
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| PCT/EP2007/056224 WO2007147879A1 (fr) | 2006-06-21 | 2007-06-21 | Derives de 1,3-diphenylpropane substitues, preparations et utilisations |
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| FR2902789A1 (fr) * | 2006-06-21 | 2007-12-28 | Genfit Sa | Derives de 1,3-diphenylpropane substitues, preparations et utilisations |
| FR2917084B1 (fr) * | 2007-06-05 | 2009-07-17 | Galderma Res & Dev | Nouveaux derives d'acide 3-phenyl propanoique activateurs des recpteurs de type ppar, leur methode de preparation et leur utilisation dans des compositions cosmetiques ou pharmaceutiques. |
| SI2504005T1 (sl) * | 2009-11-26 | 2014-04-30 | Genfit | Uporaba 1,3-difenilprop-2-en-1-on derivatov za zdravljenje ledviäśnih bolezni |
| US10722575B2 (en) | 2009-11-26 | 2020-07-28 | Genfit | Use of 1,3-diphenylprop-2-en-1-one derivatives for treating liver disorders |
| US9221751B2 (en) | 2009-11-26 | 2015-12-29 | Genfit | Use of 1,3-diphenylprop-2-en-1-one derivatives for treating liver disorders |
| 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 |
| AU2011254670B2 (en) | 2010-05-17 | 2014-09-25 | Genfit | Improved preparation of chalcone derivatives |
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| US20230165821A1 (en) * | 2020-05-18 | 2023-06-01 | Genfit | Elafibranor for the treatment of primary sclerosing cholangitis |
| KR20230058104A (ko) | 2020-08-26 | 2023-05-02 | 장피트 | 원발 담즙성 담관염의 치료를 위한 조성물 및 방법 |
| WO2022238450A1 (en) | 2021-05-11 | 2022-11-17 | Genfit | Ppar-agonists for use in the treatment of liver failure |
| EP4337185A1 (en) | 2021-05-11 | 2024-03-20 | Genfit | Elafibranor derivatives agonists of ppar for use in the treatment of sepsis |
| TW202527918A (zh) | 2023-10-13 | 2025-07-16 | 法商Genfit公司 | 原發性膽汁性膽管炎之治療方法 |
| TW202523277A (zh) | 2023-10-25 | 2025-06-16 | 法商Genfit公司 | 原發性膽汁性膽管炎的治療 |
| WO2025215081A1 (en) | 2024-04-09 | 2025-10-16 | Genfit | Elafibranor for use for long-term treatment of primary biliary cholangitis |
| CN119490528A (zh) * | 2025-01-17 | 2025-02-21 | 山东第一医科大学附属肿瘤医院(山东省肿瘤防治研究院、山东省肿瘤医院) | 一种HSP90α选择性抑制剂及其合成方法和应用 |
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