AU746991B2 - Selective thyroid hormone analogs - Google Patents
Selective thyroid hormone analogs Download PDFInfo
- Publication number
- AU746991B2 AU746991B2 AU78234/98A AU7823498A AU746991B2 AU 746991 B2 AU746991 B2 AU 746991B2 AU 78234/98 A AU78234/98 A AU 78234/98A AU 7823498 A AU7823498 A AU 7823498A AU 746991 B2 AU746991 B2 AU 746991B2
- Authority
- AU
- Australia
- Prior art keywords
- formula
- compound
- hydrogen
- compounds
- lower alkyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
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- 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 title claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 41
- 239000005495 thyroid hormone Substances 0.000 claims abstract description 19
- 229940036555 thyroid hormone Drugs 0.000 claims abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
- 239000000556 agonist Substances 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims description 178
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 60
- 239000001257 hydrogen Substances 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 239000000203 mixture Substances 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 201000010099 disease Diseases 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 18
- 238000011282 treatment Methods 0.000 claims description 14
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000000753 cycloalkyl group Chemical group 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 241000124008 Mammalia Species 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 208000008589 Obesity Diseases 0.000 claims description 4
- 235000020824 obesity Nutrition 0.000 claims description 4
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 3
- 206010003119 arrhythmia Diseases 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 208000003532 hypothyroidism Diseases 0.000 claims description 3
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- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 2
- 208000001132 Osteoporosis Diseases 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 66
- 230000027455 binding Effects 0.000 abstract description 7
- 108010071769 Thyroid Hormone Receptors beta Proteins 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- 238000006243 chemical reaction Methods 0.000 description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 28
- -1 hydrocarbon radical Chemical class 0.000 description 26
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Classifications
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- 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
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- 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
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- 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)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Child & Adolescent Psychology (AREA)
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- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (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)
- Compounds Of Unknown Constitution (AREA)
- Medicinal Preparation (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (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 |
|---|---|---|---|
| US08/877,792 US5883294A (en) | 1997-06-18 | 1997-06-18 | Selective thyroid hormone analogs |
| US08/877792 | 1997-06-18 | ||
| PCT/US1998/011758 WO1998057919A1 (en) | 1997-06-18 | 1998-06-08 | Selective thyroid hormone analogs |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU7823498A AU7823498A (en) | 1999-01-04 |
| AU746991B2 true AU746991B2 (en) | 2002-05-09 |
Family
ID=25370738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU78234/98A Ceased AU746991B2 (en) | 1997-06-18 | 1998-06-08 | Selective thyroid hormone analogs |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5883294A (enExample) |
| EP (1) | EP0991618B1 (enExample) |
| JP (1) | JP2002511084A (enExample) |
| KR (1) | KR20010013999A (enExample) |
| AT (1) | ATE254095T1 (enExample) |
| AU (1) | AU746991B2 (enExample) |
| CA (1) | CA2290622C (enExample) |
| DE (1) | DE69819726T2 (enExample) |
| WO (1) | WO1998057919A1 (enExample) |
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|---|---|---|---|---|
| EP0873361B1 (en) | 1995-12-13 | 2006-11-02 | The Regents Of The University Of California | Crystals of the ligand-binding domain of the thyroid hormone receptor complexed to a ligand |
| US6266622B1 (en) * | 1995-12-13 | 2001-07-24 | Regents Of The University Of California | 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 |
| EP1598334A1 (en) * | 1998-06-30 | 2005-11-23 | The Regents Of The University Of California | Thyroid hormone analogues and methods for their preparation |
| AR018699A1 (es) | 1999-06-01 | 2001-11-28 | Procter & Gamble | Metodo para el tratamiento de la perdida del cabello el cual comprende administrar una composicion que comprende un compuesto el cual no afecta al corazon |
| US6680344B1 (en) | 1999-06-01 | 2004-01-20 | The University Of Texas Southwestern Medical Center | Method of treating hair loss using diphenylmethane derivatives |
| 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 |
| CA2374263A1 (en) | 1999-06-01 | 2000-12-07 | The University Of Texas Southwestern Medical Center | Method of treating hair loss using diphenylether derivatives |
| WO2000072813A1 (en) * | 1999-06-01 | 2000-12-07 | The University Of Texas Southwestern Medical Center | Method of treating hair loss using diphenylmethane 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 |
| CA2433100A1 (en) | 2000-12-27 | 2002-07-04 | Helmut Haning | Indole derivatives as ligands of thyroid receptors |
| 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 |
| 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 |
| 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 |
| US6777442B2 (en) | 2001-03-12 | 2004-08-17 | Bayer Aktiengesellschaft | Diphenyl derivatives |
| US20040253648A1 (en) * | 2002-12-10 | 2004-12-16 | The Regents Of The University Of California | Method for creating nuclear receptor activity modulating pharmaceuticals |
| US7302347B2 (en) * | 2002-12-10 | 2007-11-27 | The Regents Of The University Of California | Method for creating specific, high affinity nuclear receptor pharmaceuticals |
| CA2546601A1 (en) * | 2003-11-19 | 2005-06-09 | Metabasis Therapeutics, Inc. | Novel phosphorus-containing thyromimetics |
| WO2005085865A2 (en) * | 2004-03-09 | 2005-09-15 | Bayer Healthcare Ag | Diagnostics and therapeutics for diseases associated with thyroid hormone receptor beta (thrb) |
| US20090232879A1 (en) | 2005-05-26 | 2009-09-17 | Metabasis Therapeutics, Inc. | Thyromimetics for the Treatment of Fatty Liver Diseases |
| RU2007148927A (ru) * | 2005-05-26 | 2009-07-10 | Метабэйзис Терапьютикс, Инк. (Us) | Новые тиреомиметики, содержащие фосфиновую кислоту |
| US20060292194A1 (en) * | 2005-06-24 | 2006-12-28 | Thomas Lavin | Treatment for burns and adipose deposits using thyroid hormone compound in a human |
| KR100965006B1 (ko) | 2005-07-21 | 2010-06-21 | 에프. 호프만-라 로슈 아게 | 갑상선 호르몬 수용체 작용제로서 피리다진온 유도체 |
| GB0606212D0 (en) * | 2006-03-28 | 2006-05-10 | Karobio Ab | Pharmaceutical compositions |
| AU2008219585A1 (en) * | 2007-02-27 | 2008-09-04 | The Arizona Board Of Regents On Behalf Of The University Of Arizona | 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 |
| JP2016517883A (ja) | 2013-05-03 | 2016-06-20 | オレゴン ヘルス アンド サイエンス ユニバーシティー | Ｘ連鎖副腎白質ジストロフィーの処置におけるソベチロムの使用 |
| JP2018510849A (ja) * | 2015-02-20 | 2018-04-19 | オレゴン・ヘルス・アンド・サイエンス・ユニバーシティ | ソベチロムの誘導体 |
| US11872207B2 (en) | 2015-12-24 | 2024-01-16 | Mcmaster University | Dronedarone and derivatives thereof for treating cancer |
| CA3008041C (en) | 2015-12-24 | 2024-02-13 | Mcmaster University | Compounds for treating cancer |
| KR102331596B1 (ko) | 2016-05-18 | 2021-11-25 | 오레곤 헬스 앤드 사이언스 유니버시티 | 소베티롬의 유도체 |
| US11325886B2 (en) | 2016-08-12 | 2022-05-10 | Oregon Health & Science University | Amide compounds, pharmaceutical compositions thereof, and methods of using the same |
| JP2020500199A (ja) | 2016-11-21 | 2020-01-09 | バイキング・セラピューティクス・インコーポレイテッド | グリコーゲン蓄積症の治療方法 |
| AU2018280118B2 (en) | 2017-06-05 | 2021-07-15 | 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 |
| WO2019160980A1 (en) | 2018-02-14 | 2019-08-22 | Oregon Health & Science University | Derivatives of sobetirome |
| EA202091979A1 (ru) | 2018-03-22 | 2021-06-22 | Вайкинг Терапьютикс, Инк. | Кристаллические формы и способы получения кристаллических форм соединения |
| US12102646B2 (en) | 2018-12-05 | 2024-10-01 | Viking Therapeutics, Inc. | Compositions for the treatment of fibrosis and inflammation |
| CA3122996A1 (en) | 2018-12-12 | 2020-06-18 | Autobahn Therapeutics, Inc. | Novel thyromimetics |
| EP3931180A1 (en) | 2019-03-01 | 2022-01-05 | 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 |
| JP2023530708A (ja) * | 2020-06-17 | 2023-07-19 | 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 |
| US20230242473A1 (en) * | 2020-06-17 | 2023-08-03 | Autobahn Therapeutics, Inc. | Thyromimetics |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4323691A (en) * | 1979-10-09 | 1982-04-06 | Abbott Laboratories | Hydroxyaminomethyl derivatives of benzoyl di-substituted α-phenoxyalkanoyl esters |
| CA1149803A (en) * | 1979-10-09 | 1983-07-12 | Carroll W. Ours | HYDROXYAMINOMETHYL DERIVATIVES OF BENZOYL DI-SUBSTITUTED .alpha.-PHENOXY ALKANOYL 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 |
| EP1598334A1 (en) * | 1998-06-30 | 2005-11-23 | The Regents Of The University Of California | Thyroid hormone analogues and methods for their preparation |
-
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 CA CA002290622A patent/CA2290622C/en not_active Expired - Fee Related
- 1998-06-08 AT AT98926384T patent/ATE254095T1/de not_active IP Right Cessation
- 1998-06-08 EP EP98926384A patent/EP0991618B1/en not_active Expired - Lifetime
- 1998-06-08 JP JP50453099A patent/JP2002511084A/ja not_active Ceased
- 1998-06-08 AU AU78234/98A patent/AU746991B2/en not_active Ceased
- 1998-06-08 DE DE69819726T patent/DE69819726T2/de not_active Expired - Lifetime
- 1998-06-08 WO PCT/US1998/011758 patent/WO1998057919A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| KR20010013999A (ko) | 2001-02-26 |
| DE69819726T2 (de) | 2004-09-30 |
| EP0991618A1 (en) | 2000-04-12 |
| CA2290622C (en) | 2008-08-05 |
| JP2002511084A (ja) | 2002-04-09 |
| CA2290622A1 (en) | 1998-12-23 |
| WO1998057919A1 (en) | 1998-12-23 |
| EP0991618A4 (en) | 2000-09-27 |
| AU7823498A (en) | 1999-01-04 |
| US5883294A (en) | 1999-03-16 |
| ATE254095T1 (de) | 2003-11-15 |
| DE69819726D1 (de) | 2003-12-18 |
| EP0991618B1 (en) | 2003-11-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) |