NO312586B1 - Nye forbindelser med retinoid antagonist eller retinoid invers agonist type biologisk aktivitet - Google Patents
Nye forbindelser med retinoid antagonist eller retinoid invers agonist type biologisk aktivitet Download PDFInfo
- Publication number
- NO312586B1 NO312586B1 NO19992871A NO992871A NO312586B1 NO 312586 B1 NO312586 B1 NO 312586B1 NO 19992871 A NO19992871 A NO 19992871A NO 992871 A NO992871 A NO 992871A NO 312586 B1 NO312586 B1 NO 312586B1
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- Norway
- Prior art keywords
- sub
- compound
- alkyl
- compounds
- retinoid
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 225
- 150000004492 retinoid derivatives Chemical class 0.000 title description 35
- 239000005557 antagonist Substances 0.000 title description 30
- 229940125425 inverse agonist Drugs 0.000 title description 15
- 230000004071 biological effect Effects 0.000 title description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 27
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 18
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims abstract description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- -1 6-methyl(3-pyridyl) Chemical group 0.000 claims description 35
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000001544 thienyl group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 abstract description 10
- 125000000304 alkynyl group Chemical group 0.000 abstract description 7
- 229910052794 bromium Inorganic materials 0.000 abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- 229910052717 sulfur Inorganic materials 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 abstract 1
- 125000004469 siloxy group Chemical group [SiH3]O* 0.000 abstract 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 93
- 239000000203 mixture Substances 0.000 description 82
- 238000006243 chemical reaction Methods 0.000 description 76
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- 239000000243 solution Substances 0.000 description 68
- 239000002904 solvent Substances 0.000 description 46
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 40
- 239000012267 brine Substances 0.000 description 39
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 39
- 230000000694 effects Effects 0.000 description 34
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 238000000034 method Methods 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
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- WHFSBRHJIWVCDM-UHFFFAOYSA-N 2h-benzo[g]chromene Chemical compound C1=CC=C2C=C(C=CCO3)C3=CC2=C1 WHFSBRHJIWVCDM-UHFFFAOYSA-N 0.000 description 8
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- 239000000126 substance Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 7
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/66—Polycyclic acids with unsaturation outside the aromatic rings
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- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/548—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings having unsaturation outside the six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—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
- C07D213/02—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
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/55—Acids; Esters
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/08—Naphthothiopyrans; Hydrogenated naphthothiopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- General Health & Medical Sciences (AREA)
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- Hospice & Palliative Care (AREA)
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- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/764,466 US5728846A (en) | 1996-12-12 | 1996-12-12 | Benzo 1,2-g!-chrom-3-ene and benzo 1,2-g!-thiochrom-3-ene derivatives |
PCT/US1997/022581 WO1998025875A1 (fr) | 1996-12-12 | 1997-12-09 | 3,4-dihydroanthracene a substitution aryl ou heteroaryl et de benzo [1,2-g]-chrom-3-ene a substitution aryl ou heteroaryl, benzo [1,2-g]-thiochrom-3-ene et derives de benzo [1,2-g]-1,2-dihydroquinoline a activite biologique de type antagoniste des retinoides ou agoniste inverse des retinoides |
Publications (3)
Publication Number | Publication Date |
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NO992871D0 NO992871D0 (no) | 1999-06-11 |
NO992871L NO992871L (no) | 1999-08-11 |
NO312586B1 true NO312586B1 (no) | 2002-06-03 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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NO19992871A NO312586B1 (no) | 1996-12-12 | 1999-06-11 | Nye forbindelser med retinoid antagonist eller retinoid invers agonist type biologisk aktivitet |
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Country | Link |
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US (5) | US5728846A (fr) |
EP (1) | EP0948478B1 (fr) |
JP (1) | JP2001505914A (fr) |
KR (1) | KR20000069375A (fr) |
CN (1) | CN1102573C (fr) |
AT (1) | ATE215925T1 (fr) |
AU (1) | AU728051B2 (fr) |
BR (1) | BR9714023B1 (fr) |
CA (1) | CA2274838A1 (fr) |
DE (1) | DE69711923T2 (fr) |
ES (1) | ES2176813T3 (fr) |
IL (1) | IL129925A0 (fr) |
NO (1) | NO312586B1 (fr) |
NZ (1) | NZ335651A (fr) |
WO (1) | WO1998025875A1 (fr) |
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US5264578A (en) | 1987-03-20 | 1993-11-23 | Allergan, Inc. | Disubstituted acetylenes bearing heterobicyclic groups and heteroaromatic or phenyl groups having retinoid like activity |
US6008204A (en) | 1995-09-01 | 1999-12-28 | Allergan Sales, Inc. | Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities |
US5958954A (en) | 1995-09-01 | 1999-09-28 | Allergan Sales, Inc. | Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities |
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US5763635A (en) | 1996-06-21 | 1998-06-09 | Allergan | Tetrahydronaphthalene derivatives substituted in the 8 position with alkyhidene groups having retinoid and/or retinoid antagonist-like biological activity |
FR2755011B1 (fr) * | 1996-10-31 | 1998-11-20 | Cird Galderma | Utilisation des inhibiteurs de l'activite de l'acide retinoique pour traiter les peaux sensibles et/ou les dommages aigus induits par les rayonnements u.v. |
US5728846A (en) * | 1996-12-12 | 1998-03-17 | Allergan | Benzo 1,2-g!-chrom-3-ene and benzo 1,2-g!-thiochrom-3-ene derivatives |
ATE295360T1 (de) * | 1996-12-12 | 2005-05-15 | Shionogi & Co | Kondensierte heterocyclische benzolcarbonsäureamid-derivate und diese enthaltende pgd2 antagonisten |
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ATE365158T1 (de) | 1999-04-28 | 2007-07-15 | Inst Med Molecular Design Inc | Pyrimidincarbonsäurederivate |
US6043381A (en) | 1999-05-07 | 2000-03-28 | Allergan Sales, Inc. | Process for preparing substituted benzo[1,2-g]-chrom-3-ene, benzo[1,2-g]-thiochrom-3-ene and benzo[1,2-g]-1,2-dihydroquinoline derivatives |
US7268148B2 (en) * | 1999-05-20 | 2007-09-11 | Regents Of The University Of Michigan | Compositions and methods for use against acne-induced inflammation and dermal matrix-degrading enzymes |
US20040235950A1 (en) * | 1999-05-20 | 2004-11-25 | Voorhees John J. | Compositions and methods for use against acne-induced inflammation and dermal matrix-degrading enzymes |
US6436993B1 (en) | 1999-07-13 | 2002-08-20 | The Salk Institute For Biological Studies | Use of RAR antagonists as modulators of hormone mediated processes |
WO2001007028A2 (fr) * | 1999-07-23 | 2001-02-01 | Allergan Sales, Inc. | Utilisation d'antagonistes de recepteurs de retinoides dans le traitement du cancer de la prostate |
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US20030114482A1 (en) * | 1999-12-15 | 2003-06-19 | Maurizio Pacifici | Use of retinoid receptor antagonists or agonists in the treatment of cartilage and bone pathologies |
WO2002022113A2 (fr) | 2000-09-13 | 2002-03-21 | Bristol-Myers Squibb Company | Antagonistes vis-a-vis du recepteur d'acide retinoique, tenant lieu de promoteurs de l'angiogenese |
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WO2003059884A1 (fr) * | 2001-12-21 | 2003-07-24 | X-Ceptor Therapeutics, Inc. | Modulateurs de lxr |
US7482366B2 (en) | 2001-12-21 | 2009-01-27 | X-Ceptor Therapeutics, Inc. | Modulators of LXR |
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DK2026778T3 (en) * | 2006-05-16 | 2019-01-07 | Io Therapeutics Llc | RAR ANTAGONIST OR INVERSE AGONIST FOR USE IN THE TREATMENT OF CHEMOTHERAPY AND / OR RADIATION THERAPY SIDE EFFECTS |
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NZ741393A (en) | 2015-10-31 | 2018-11-30 | Io Therapeutics Inc | Treatment of nervous system disorders using combinations of rxr agonists and thyroid hormones |
EP3426302B1 (fr) | 2016-03-10 | 2022-12-14 | IO Therapeutics, Inc. | Traitement de maladies auto-immunes à l'aide de combinaisons d'agonistes de rxr et d'hormones thyroïdiennes |
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KR20240119103A (ko) | 2021-12-07 | 2024-08-06 | 아이오 테라퓨틱스, 인크. | Her2+ 암 치료에서의 rxr 작용제 및 탁산의 용도 |
KR20240115316A (ko) | 2021-12-07 | 2024-07-25 | 아이오 테라퓨틱스, 인크. | 약물 내성 her2+ 암 치료에서의 rxr 작용제의 용도 |
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-
1996
- 1996-12-12 US US08/764,466 patent/US5728846A/en not_active Expired - Fee Related
-
1997
- 1997-12-09 AT AT97953123T patent/ATE215925T1/de not_active IP Right Cessation
- 1997-12-09 BR BRPI9714023-6A patent/BR9714023B1/pt not_active IP Right Cessation
- 1997-12-09 CN CN97180511A patent/CN1102573C/zh not_active Expired - Fee Related
- 1997-12-09 AU AU56929/98A patent/AU728051B2/en not_active Ceased
- 1997-12-09 DE DE69711923T patent/DE69711923T2/de not_active Expired - Fee Related
- 1997-12-09 WO PCT/US1997/022581 patent/WO1998025875A1/fr not_active Application Discontinuation
- 1997-12-09 EP EP97953123A patent/EP0948478B1/fr not_active Expired - Lifetime
- 1997-12-09 CA CA002274838A patent/CA2274838A1/fr not_active Abandoned
- 1997-12-09 ES ES97953123T patent/ES2176813T3/es not_active Expired - Lifetime
- 1997-12-09 NZ NZ335651A patent/NZ335651A/xx unknown
- 1997-12-09 KR KR1019997005101A patent/KR20000069375A/ko not_active Application Discontinuation
- 1997-12-09 JP JP52690498A patent/JP2001505914A/ja active Pending
- 1997-12-09 IL IL12992597A patent/IL129925A0/xx unknown
-
1998
- 1998-02-25 US US09/030,350 patent/US6087505A/en not_active Expired - Fee Related
-
1999
- 1999-06-11 NO NO19992871A patent/NO312586B1/no not_active IP Right Cessation
-
2000
- 2000-01-13 US US09/482,700 patent/US6538149B1/en not_active Expired - Fee Related
-
2003
- 2003-01-02 US US10/336,344 patent/US7166726B2/en not_active Expired - Fee Related
-
2006
- 2006-12-21 US US11/643,754 patent/US20070265449A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
ATE215925T1 (de) | 2002-04-15 |
CA2274838A1 (fr) | 1998-06-18 |
AU728051B2 (en) | 2001-01-04 |
CN1102573C (zh) | 2003-03-05 |
NO992871D0 (no) | 1999-06-11 |
US6087505A (en) | 2000-07-11 |
JP2001505914A (ja) | 2001-05-08 |
WO1998025875A1 (fr) | 1998-06-18 |
BR9714023B1 (pt) | 2009-12-01 |
US6538149B1 (en) | 2003-03-25 |
NO992871L (no) | 1999-08-11 |
US20070265449A1 (en) | 2007-11-15 |
CN1239941A (zh) | 1999-12-29 |
US20030130515A1 (en) | 2003-07-10 |
BR9714023A (pt) | 2000-05-09 |
EP0948478B1 (fr) | 2002-04-10 |
NZ335651A (en) | 2000-09-29 |
DE69711923T2 (de) | 2002-10-31 |
IL129925A0 (en) | 2000-02-29 |
US5728846A (en) | 1998-03-17 |
EP0948478A1 (fr) | 1999-10-13 |
DE69711923D1 (de) | 2002-05-16 |
KR20000069375A (ko) | 2000-11-25 |
US7166726B2 (en) | 2007-01-23 |
ES2176813T3 (es) | 2002-12-01 |
AU5692998A (en) | 1998-07-03 |
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