DE69819726T2 - Selektive analoge der thyroidhormone - Google Patents
Selektive analoge der thyroidhormone Download PDFInfo
- Publication number
- DE69819726T2 DE69819726T2 DE69819726T DE69819726T DE69819726T2 DE 69819726 T2 DE69819726 T2 DE 69819726T2 DE 69819726 T DE69819726 T DE 69819726T DE 69819726 T DE69819726 T DE 69819726T DE 69819726 T2 DE69819726 T2 DE 69819726T2
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- compound
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- compounds
- alkyl
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- Expired - Lifetime
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- 239000005495 thyroid hormone Substances 0.000 title claims abstract description 19
- 229940036555 thyroid hormone Drugs 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 35
- 239000000556 agonist Substances 0.000 claims abstract description 11
- AUYYCJSJGJYCDS-LBPRGKRZSA-N Thyrolar Chemical class IC1=CC(C[C@H](N)C(O)=O)=CC(I)=C1OC1=CC=C(O)C(I)=C1 AUYYCJSJGJYCDS-LBPRGKRZSA-N 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims description 157
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 71
- 239000001257 hydrogen Substances 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 40
- 238000004519 manufacturing process Methods 0.000 claims description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
- -1 nitro, amino Chemical group 0.000 claims description 22
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 18
- 201000010099 disease Diseases 0.000 claims description 17
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
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- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
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- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 230000023603 positive regulation of transcription initiation, DNA-dependent Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
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- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000001525 receptor binding assay Methods 0.000 description 1
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- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
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- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- KUYMVWXKHQSIAS-UHFFFAOYSA-N tert-butyl 2-chloroacetate Chemical compound CC(C)(C)OC(=O)CCl KUYMVWXKHQSIAS-UHFFFAOYSA-N 0.000 description 1
- 229960004559 theobromine Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 238000005199 ultracentrifugation Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/84—Unsaturated compounds containing keto groups containing six membered aromatic rings
-
- 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
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
- C07C59/70—Ethers of hydroxy-acetic acid, e.g. substitutes on the ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Physical Education & Sports Medicine (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Child & Adolescent Psychology (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Compounds Of Unknown Constitution (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US877792 | 1992-05-04 | ||
| US08/877,792 US5883294A (en) | 1997-06-18 | 1997-06-18 | Selective thyroid hormone analogs |
| PCT/US1998/011758 WO1998057919A1 (en) | 1997-06-18 | 1998-06-08 | Selective thyroid hormone analogs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69819726D1 DE69819726D1 (de) | 2003-12-18 |
| DE69819726T2 true DE69819726T2 (de) | 2004-09-30 |
Family
ID=25370738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69819726T Expired - Lifetime DE69819726T2 (de) | 1997-06-18 | 1998-06-08 | Selektive analoge der thyroidhormone |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5883294A (https=) |
| EP (1) | EP0991618B1 (https=) |
| JP (1) | JP2002511084A (https=) |
| KR (1) | KR20010013999A (https=) |
| AT (1) | ATE254095T1 (https=) |
| AU (1) | AU746991B2 (https=) |
| CA (1) | CA2290622C (https=) |
| DE (1) | DE69819726T2 (https=) |
| WO (1) | WO1998057919A1 (https=) |
Families Citing this family (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6266622B1 (en) * | 1995-12-13 | 2001-07-24 | Regents Of The University Of California | Nuclear receptor ligands and ligand binding domains |
| AU717743B2 (en) | 1995-12-13 | 2000-03-30 | Regents Of The University Of California, The | Nuclear receptor ligands and ligand binding domains |
| US6017958A (en) * | 1996-06-04 | 2000-01-25 | Octamer, Inc. | Method of treating malignant tumors with thyroxine analogues having no significant hormonal activity |
| US6217598B1 (en) * | 1997-11-25 | 2001-04-17 | Linvatec Corporation | End-cutting shaver blade |
| DE69924846T2 (de) * | 1998-06-30 | 2006-04-27 | The Regents Of The University Of California, Oakland | Thyroidhormon-analoga und verfahren zu ihrer herstellung |
| US6723717B1 (en) | 1999-06-01 | 2004-04-20 | The University Of Texas Southwestern Medical Center | Sulfur-containing thyroxane derivatives and their use as hair growth promotors |
| CA2374260A1 (en) | 1999-06-01 | 2000-12-07 | The University Of Texas Southwestern Medical Center | Method of treating hair loss using sulfonyl thyromimetic compounds |
| US6680344B1 (en) | 1999-06-01 | 2004-01-20 | The University Of Texas Southwestern Medical Center | Method of treating hair loss using diphenylmethane derivatives |
| CA2374266A1 (en) * | 1999-06-01 | 2000-12-07 | The University Of Texas Southwestern Medical Center | Method of treating hair loss using diphenylmethane derivatives |
| CA2374263A1 (en) | 1999-06-01 | 2000-12-07 | The University Of Texas Southwestern Medical Center | Method of treating hair loss using diphenylether derivatives |
| US6516294B1 (en) | 1999-07-01 | 2003-02-04 | The Regents Of The University Of California | Nuclear receptor for 1α,25-dihydroxyvitamin D3 useful for selection of vitamin D3 ligands and a method therefor |
| DE10024939A1 (de) | 2000-05-19 | 2001-11-29 | Bayer Ag | Neue Diphenylmethanderivate für Arzneimittel |
| GB0015205D0 (en) * | 2000-06-21 | 2000-08-09 | Karobio Ab | Bioisosteric thyroid receptor ligands and method |
| DE10046029A1 (de) | 2000-09-18 | 2002-03-28 | Bayer Ag | Indazole |
| WO2002051805A1 (de) * | 2000-12-27 | 2002-07-04 | Bayer Aktiengesellschaft | Indol-derivate |
| US7504435B2 (en) * | 2001-01-31 | 2009-03-17 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Method for stimulating weight loss and/or for lowering triglycerides in patients |
| US6534676B2 (en) | 2001-01-31 | 2003-03-18 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Method to treat chronic heart failure and/or elevated cholesterol levels using 3,5-diiodothyropropionic acid and method to prepare same |
| US6716877B2 (en) | 2001-01-31 | 2004-04-06 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | Method to treat chronic heart failure and/or elevated cholesterol levels |
| US6777442B2 (en) | 2001-03-12 | 2004-08-17 | Bayer Aktiengesellschaft | Diphenyl derivatives |
| US7302347B2 (en) * | 2002-12-10 | 2007-11-27 | The Regents Of The University Of California | Method for creating specific, high affinity nuclear receptor pharmaceuticals |
| AU2003300852A1 (en) * | 2002-12-10 | 2004-06-30 | The Regents Of The University Of California | A method for creating specific, high affinity nuclear receptor pharmaceuticals |
| WO2006128058A2 (en) | 2005-05-26 | 2006-11-30 | Metabasis Therapeutics, Inc. | Thyromimetics for the treatment of fatty liver diseases |
| CN1882327A (zh) * | 2003-11-19 | 2006-12-20 | 症变治疗公司 | 含磷的新的拟甲状腺素药 |
| WO2005085865A2 (en) * | 2004-03-09 | 2005-09-15 | Bayer Healthcare Ag | Diagnostics and therapeutics for diseases associated with thyroid hormone receptor beta (thrb) |
| WO2006128056A2 (en) * | 2005-05-26 | 2006-11-30 | Metabasis Therapeutics, Inc. | Novel phosphinic acid-containing thyromimetics |
| WO2007002036A1 (en) * | 2005-06-24 | 2007-01-04 | Thomas Lavin | Tyroid hormone in burn and adipose deposites |
| PL1919878T3 (pl) | 2005-07-21 | 2011-03-31 | Hoffmann La Roche | Pochodne pirydazynonu jako agoniści receptora hormonu tarczycy |
| GB0606212D0 (en) * | 2006-03-28 | 2006-05-10 | Karobio Ab | Pharmaceutical compositions |
| WO2008106213A1 (en) * | 2007-02-27 | 2008-09-04 | Titan Pharmaceuticals, Inc. | Administration of 3,5-diiodothyropropionic acid for stimulating weight loss, and/or lowering triglyceride levels, and/or treatment of metabolic syndrome. |
| US8076334B2 (en) | 2007-09-20 | 2011-12-13 | Hoffmann-La Roche Inc. | Prodrugs of thyroid hormone analogs |
| WO2009089093A1 (en) * | 2008-01-04 | 2009-07-16 | Quatrx Pharmaceuticals Company | Thyroid hormone receptor agonists |
| WO2014178892A1 (en) | 2013-05-03 | 2014-11-06 | Scanlan Thomas S | Use of sobetirome in the treatment of x-linked adrenolenoleukodystrophy |
| EP3259246B1 (en) | 2015-02-20 | 2023-03-22 | Oregon Health & Science University | Derivatives of sobetirome |
| WO2017106974A1 (en) | 2015-12-24 | 2017-06-29 | Mcmaster University | Compounds for targeting thyroid hormone receptor alpha isoforms and methods of use thereof |
| US11872207B2 (en) | 2015-12-24 | 2024-01-16 | Mcmaster University | Dronedarone and derivatives thereof for treating cancer |
| CN109475121B (zh) | 2016-05-18 | 2021-06-25 | 俄勒冈健康科学大学 | 苏比替罗衍生物 |
| US11325886B2 (en) | 2016-08-12 | 2022-05-10 | Oregon Health & Science University | Amide compounds, pharmaceutical compositions thereof, and methods of using the same |
| CA3044059A1 (en) | 2016-11-21 | 2018-05-24 | Viking Therapeutics, Inc. | Method of treating glycogen storage disease |
| US11707472B2 (en) | 2017-06-05 | 2023-07-25 | Viking Therapeutics, Inc. | Compositions for the treatment of fibrosis |
| US11660281B2 (en) * | 2017-06-29 | 2023-05-30 | Yale University | Compositions and methods of treating or preventing fibrotic lung diseases |
| IL276592B2 (en) | 2018-02-14 | 2023-11-01 | Univ Oregon Health & Science | History of Subtirum |
| ES3053674T3 (en) | 2018-03-22 | 2026-01-23 | Viking Therapeutics Inc | Crystalline forms and methods of producing crystalline forms of a compound |
| WO2020117962A1 (en) | 2018-12-05 | 2020-06-11 | Viking Therapeutics, Inc. | Compositions for the treatment of fibrosis and inflammation |
| EP3894383A1 (en) | 2018-12-12 | 2021-10-20 | Autobahn Therapeutics, Inc. | Novel thyromimetics |
| CA3130371A1 (en) | 2019-03-01 | 2020-09-10 | Autobahn Therapeutics, Inc. | Novel thyromimetics |
| IT201900006923A1 (it) * | 2019-05-16 | 2020-11-16 | International Soc For Drug Development S R L | Nuovi tiromimetici con uno scaffold bifenilmetano e loro uso |
| KR20220121239A (ko) | 2019-11-29 | 2022-08-31 | 아우토반 쎄라퓨틱스, 인크. | 신규한 갑상선 호르몬 모방제 |
| CN111116684B (zh) | 2019-12-31 | 2020-09-25 | 厦门甘宝利生物医药有限公司 | 一种具有甲状腺激素受体激动剂特性的肝靶向化合物及其药物组合物 |
| US20230242473A1 (en) * | 2020-06-17 | 2023-08-03 | Autobahn Therapeutics, Inc. | Thyromimetics |
| JP7813730B2 (ja) | 2020-06-17 | 2026-02-13 | オートバーン セラピューティクス，インク． | 甲状腺様作用剤 |
| WO2021257851A1 (en) * | 2020-06-17 | 2021-12-23 | Autobahn Therapeutics, Inc. | Thyromimetics |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1149803A (en) * | 1979-10-09 | 1983-07-12 | Carroll W. Ours | HYDROXYAMINOMETHYL DERIVATIVES OF BENZOYL DI-SUBSTITUTED .alpha.-PHENOXY ALKANOYL ESTERS |
| US4323691A (en) * | 1979-10-09 | 1982-04-06 | Abbott Laboratories | Hydroxyaminomethyl derivatives of benzoyl di-substituted α-phenoxyalkanoyl esters |
| IT1218855B (it) * | 1984-12-28 | 1990-04-24 | Ates Componenti Elettron | Stadio amplificatore di segnali, integrato monoliticamente, ad alta dinamica di uscita |
| GB8501372D0 (en) * | 1985-01-18 | 1985-02-20 | Smith Kline French Lab | Chemical compounds |
| JPH05170690A (ja) * | 1991-12-20 | 1993-07-09 | Mitsui Toatsu Chem Inc | ジフェニル炭化水素誘導体を有効成分として含有する血栓溶解促進剤 |
| DE4327365A1 (de) * | 1993-08-14 | 1995-02-16 | Boehringer Mannheim Gmbh | Verwendung von Phenolen und Phenolderivaten als Arzneimittel mit fibrinogensenkender Wirkung |
| DE69924846T2 (de) * | 1998-06-30 | 2006-04-27 | The Regents Of The University Of California, Oakland | Thyroidhormon-analoga und verfahren zu ihrer herstellung |
-
1997
- 1997-06-18 US US08/877,792 patent/US5883294A/en not_active Expired - Lifetime
-
1998
- 1998-06-08 KR KR19997012027A patent/KR20010013999A/ko not_active Withdrawn
- 1998-06-08 AT AT98926384T patent/ATE254095T1/de not_active IP Right Cessation
- 1998-06-08 WO PCT/US1998/011758 patent/WO1998057919A1/en not_active Ceased
- 1998-06-08 EP EP98926384A patent/EP0991618B1/en not_active Expired - Lifetime
- 1998-06-08 AU AU78234/98A patent/AU746991B2/en not_active Ceased
- 1998-06-08 CA CA002290622A patent/CA2290622C/en not_active Expired - Fee Related
- 1998-06-08 JP JP50453099A patent/JP2002511084A/ja not_active Ceased
- 1998-06-08 DE DE69819726T patent/DE69819726T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ATE254095T1 (de) | 2003-11-15 |
| AU746991B2 (en) | 2002-05-09 |
| JP2002511084A (ja) | 2002-04-09 |
| EP0991618A1 (en) | 2000-04-12 |
| CA2290622A1 (en) | 1998-12-23 |
| AU7823498A (en) | 1999-01-04 |
| EP0991618A4 (en) | 2000-09-27 |
| KR20010013999A (ko) | 2001-02-26 |
| DE69819726D1 (de) | 2003-12-18 |
| EP0991618B1 (en) | 2003-11-12 |
| WO1998057919A1 (en) | 1998-12-23 |
| CA2290622C (en) | 2008-08-05 |
| US5883294A (en) | 1999-03-16 |
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