CA2412161C - Thyroid receptor ligands, pharmaceutical compositions comprising them and their use in the treatment of disorders influenced by thyroid hormones - Google Patents
Thyroid receptor ligands, pharmaceutical compositions comprising them and their use in the treatment of disorders influenced by thyroid hormones Download PDFInfo
- Publication number
- CA2412161C CA2412161C CA002412161A CA2412161A CA2412161C CA 2412161 C CA2412161 C CA 2412161C CA 002412161 A CA002412161 A CA 002412161A CA 2412161 A CA2412161 A CA 2412161A CA 2412161 C CA2412161 C CA 2412161C
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- Prior art keywords
- dichloro
- acid
- alkyl
- alkenyl
- aryl
- Prior art date
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- 108090000721 thyroid hormone receptors Proteins 0.000 title abstract description 16
- 102000004217 thyroid hormone receptors Human genes 0.000 title abstract description 16
- 239000003446 ligand Substances 0.000 title abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 15
- 239000005495 thyroid hormone Substances 0.000 title description 15
- 229940036555 thyroid hormone Drugs 0.000 title description 15
- 208000035475 disorder Diseases 0.000 title description 6
- 239000008194 pharmaceutical composition Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 76
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- 125000000217 alkyl group Chemical group 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 36
- 125000003118 aryl group Chemical group 0.000 claims description 33
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical group 0.000 claims description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 229960003424 phenylacetic acid Drugs 0.000 claims description 17
- 239000003279 phenylacetic acid Substances 0.000 claims description 17
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000000304 alkynyl group Chemical group 0.000 claims description 15
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 10
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- HHSRCUBLBZYJPA-UHFFFAOYSA-N 2-[4-[3-bromo-4-(2-methylpropanoylamino)phenoxy]-3,5-dichlorophenyl]acetic acid Chemical compound C1=C(Br)C(NC(=O)C(C)C)=CC=C1OC1=C(Cl)C=C(CC(O)=O)C=C1Cl HHSRCUBLBZYJPA-UHFFFAOYSA-N 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
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- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 claims description 7
- MUOZXUXILGIRHS-UHFFFAOYSA-N 2-[3,5-dichloro-4-[4-(2-methylpropanoylamino)-3-(trifluoromethyl)phenoxy]phenyl]acetic acid Chemical compound C1=C(C(F)(F)F)C(NC(=O)C(C)C)=CC=C1OC1=C(Cl)C=C(CC(O)=O)C=C1Cl MUOZXUXILGIRHS-UHFFFAOYSA-N 0.000 claims description 5
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- GHFDIOYOXCZYTG-UHFFFAOYSA-N 2-[4-[3-bromo-4-(2-methylpropanoylamino)phenoxy]-3,5-dichlorophenyl]propanoic acid Chemical compound C1=C(Br)C(NC(=O)C(C)C)=CC=C1OC1=C(Cl)C=C(C(C)C(O)=O)C=C1Cl GHFDIOYOXCZYTG-UHFFFAOYSA-N 0.000 claims description 4
- XYSAJNKQKHJTLF-UHFFFAOYSA-N 2-[[2-[4-[3-bromo-4-(2-methylpropanoylamino)phenoxy]-3,5-dichlorophenyl]acetyl]amino]acetic acid Chemical compound C1=C(Br)C(NC(=O)C(C)C)=CC=C1OC1=C(Cl)C=C(CC(=O)NCC(O)=O)C=C1Cl XYSAJNKQKHJTLF-UHFFFAOYSA-N 0.000 claims description 4
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 claims description 4
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- SPPOOEUONWULHW-UHFFFAOYSA-N 2-[3,5-dichloro-4-[3-chloro-4-(2-methylpropanoylamino)phenoxy]phenyl]acetic acid Chemical compound C1=C(Cl)C(NC(=O)C(C)C)=CC=C1OC1=C(Cl)C=C(CC(O)=O)C=C1Cl SPPOOEUONWULHW-UHFFFAOYSA-N 0.000 claims description 3
- DCXATCLZMIKWFQ-UHFFFAOYSA-N 2-[3,5-dichloro-4-[3-methyl-4-(2-methylpropanoylamino)phenoxy]phenyl]acetic acid Chemical compound C1=C(C)C(NC(=O)C(C)C)=CC=C1OC1=C(Cl)C=C(CC(O)=O)C=C1Cl DCXATCLZMIKWFQ-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D213/70—Sulfur atoms
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- C07C233/25—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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| PCT/EP2001/006815 WO2001098256A1 (en) | 2000-06-21 | 2001-06-15 | Thyroid receptor ligands, pharmaceutical compositions comprising them and their use in the treatment of disorders influenced by thyroid hormones |
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| AU2006249350B2 (en) | 2003-11-19 | 2012-02-16 | Metabasis Therapeutics, Inc. | Thyromimetics for the treatment of fatty liver diseases |
| WO2005054176A1 (en) * | 2003-11-25 | 2005-06-16 | Eli Lilly And Company | Peroxisome proliferator activated receptor modulators |
| WO2005090297A1 (en) * | 2004-03-19 | 2005-09-29 | Biotie Therapies Corporation | Sulphonamide derivatives |
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| US20060039890A1 (en) * | 2004-08-20 | 2006-02-23 | Renshaw Perry F | Treatment of psychological and cognitive disorders using a cholesterol -lowering agent in combination with an antidepressant |
| WO2006028835A2 (en) * | 2004-09-01 | 2006-03-16 | Trustees Of Boston University | Use of thyroid hormone conversion inhibitors |
| US20090028925A1 (en) * | 2005-05-26 | 2009-01-29 | Erion Mark D | Novel Phosphinic Acid-Containing Thyromimetics |
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| NZ575507A (en) | 2006-08-21 | 2011-10-28 | Array Biopharma Inc | 4-substituted phenoxyphenylacetic acid derivatives |
| UA95978C2 (ru) | 2006-10-02 | 2011-09-26 | Оцука Фармас'Ютікел Ко., Лтд. | Ингибитор активации stat3/5 |
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| JP2011088826A (ja) * | 2008-01-31 | 2011-05-06 | Astellas Pharma Inc | 芳香族カルボン酸化合物 |
| JP5487202B2 (ja) | 2009-04-20 | 2014-05-07 | 田辺三菱製薬株式会社 | 新規甲状腺ホルモンβ受容体作動薬 |
| CA2777234C (en) | 2009-10-11 | 2019-02-26 | Rutgers, The State University Of New Jersey | Biocompatible polymers for medical devices |
| AU2013214799B2 (en) | 2012-02-03 | 2016-05-12 | Rutgers, The State Of University Of New Jersey | Polymeric biomaterials derived from phenolic monomers and their medical uses |
| US11472918B2 (en) | 2012-02-03 | 2022-10-18 | Rutgers, The State University Of New Jersey | Polymeric biomaterials derived from phenolic monomers and their medical uses |
| US10774030B2 (en) | 2014-12-23 | 2020-09-15 | Rutgers, The State University Of New Jersey | Polymeric biomaterials derived from phenolic monomers and their medical uses |
| EP3237487B1 (en) | 2014-12-23 | 2021-02-17 | Rutgers, the State University of New Jersey | Biocompatible iodinated diphenol monomers and polymers |
| KR20190104524A (ko) | 2016-11-21 | 2019-09-10 | 바이킹 테라퓨틱스 인코포레이티드 | 당원축적질환의 치료 방법 |
| EA201992703A1 (ru) | 2017-06-05 | 2020-04-15 | Вайкинг Терапьютикс, Инк. | Композиции для лечения фиброза |
| US12090252B2 (en) | 2017-09-14 | 2024-09-17 | Riken | Method for producing retinal tissues |
| KR20200138283A (ko) | 2018-03-22 | 2020-12-09 | 바이킹 테라퓨틱스 인코포레이티드 | 결정질 형태, 및 결정질 형태의 화합물을 제조하는 방법 |
| US12102646B2 (en) | 2018-12-05 | 2024-10-01 | Viking Therapeutics, Inc. | Compositions for the treatment of fibrosis and inflammation |
| CN111320609A (zh) | 2018-12-13 | 2020-06-23 | 拓臻股份有限公司 | 一种THRβ受体激动剂化合物及其制备方法和用途 |
| US20220170098A1 (en) | 2019-03-13 | 2022-06-02 | Sumitomo Dainippon Pharma Co., Ltd. | Method for Evaluating Quality of Transplant Neural Retina, and Transplant Neural Retina Sheet |
| KR20220017917A (ko) | 2019-05-08 | 2022-02-14 | 알리고스 테라퓨틱스 인코포레이티드 | Thr-베타의 조절제 및 이의 사용 방법 |
| CA3154488A1 (en) * | 2019-08-23 | 2021-03-04 | Terns Pharmaceuticals, Inc. | Thyroid hormone receptor beta agonist compounds |
| WO2021050945A1 (en) | 2019-09-12 | 2021-03-18 | Terns, Inc. | Thyroid hormone receptor beta agonist compounds |
| CA3194226A1 (en) | 2020-09-11 | 2022-03-17 | Riken | Complex containing neural retina-containing cell aggregates and matrix, and method for manufacturing same |
| EP4201428A4 (en) | 2020-09-11 | 2024-09-11 | Sumitomo Pharma Co., Ltd. | MEDIUM FOR TISSUE INTENDED FOR TRANSPLANTATION |
| EP4240722A1 (en) * | 2020-11-06 | 2023-09-13 | Aligos Therapeutics, Inc. | Oxindoles and methods of use thereof |
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| EP4568664A1 (en) | 2023-04-07 | 2025-06-18 | Terns Pharmaceuticals, Inc. | Combination comprising a thr-beta agonist and a glp-1r agonist for use in treating a liver disorder or a cardiometabolic disease |
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| GB642159A (en) * | 1947-10-23 | 1950-08-30 | Glaxo Lab Ltd | Improvements in or relating to the preparation of diphenyl ethers |
| GB643089A (en) * | 1947-10-23 | 1950-09-15 | Glaxo Lab Ltd | Improvements in or relating to the preparation of 2:6-dihalogeno diphenyl ethers |
| US3652665A (en) * | 1970-04-20 | 1972-03-28 | Merck & Co Inc | Halo-phenoxy salicylic acids |
| US4465508A (en) * | 1979-07-18 | 1984-08-14 | Imperial Chemical Industries Plc | Diphenyl ether herbicides |
| DE69314718T2 (de) * | 1992-07-21 | 1998-02-26 | Ciba Geigy Ag | Oxamidsäure-Derivate als hypocholesterämische Mittel |
| GB9416219D0 (en) * | 1994-08-11 | 1994-10-05 | Karobio Ab | Receptor ligands |
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| US5883294A (en) * | 1997-06-18 | 1999-03-16 | The Regeants Of The University Of California | Selective thyroid hormone analogs |
| OA11839A (en) * | 1999-03-01 | 2005-08-23 | Pfizer Prod Inc | Oxamic acids and derivatives as thyroid receptor ligands. |
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- 2001-06-15 AU AU72484/01A patent/AU779880B2/en not_active Ceased
- 2001-06-15 US US10/311,524 patent/US7199265B2/en not_active Expired - Fee Related
- 2001-06-15 EP EP01951600A patent/EP1296936A1/en not_active Withdrawn
- 2001-06-15 KR KR1020027017478A patent/KR20030058952A/ko not_active Withdrawn
- 2001-06-15 WO PCT/EP2001/006815 patent/WO2001098256A1/en not_active Ceased
- 2001-06-15 JP JP2002504212A patent/JP2004501132A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP1296936A1 (en) | 2003-04-02 |
| US20040097589A1 (en) | 2004-05-20 |
| JP2004501132A (ja) | 2004-01-15 |
| GB0015205D0 (en) | 2000-08-09 |
| AU779880B2 (en) | 2005-02-17 |
| WO2001098256A1 (en) | 2001-12-27 |
| AU7248401A (en) | 2002-01-02 |
| KR20030058952A (ko) | 2003-07-07 |
| CA2412161A1 (en) | 2001-12-27 |
| US7199265B2 (en) | 2007-04-03 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |