JP2007518719A - ＲＡＲγレチノイド受容体アンタゴニスト活性を有する二置換カルコンオキシム - Google Patents
ＲＡＲγレチノイド受容体アンタゴニスト活性を有する二置換カルコンオキシム Download PDFInfo
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- JP2007518719A JP2007518719A JP2006547254A JP2006547254A JP2007518719A JP 2007518719 A JP2007518719 A JP 2007518719A JP 2006547254 A JP2006547254 A JP 2006547254A JP 2006547254 A JP2006547254 A JP 2006547254A JP 2007518719 A JP2007518719 A JP 2007518719A
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- -1 Disubstituted chalcone oximes Chemical class 0.000 title claims description 23
- 230000000694 effects Effects 0.000 title description 26
- 102100033912 Retinoic acid receptor gamma Human genes 0.000 title description 7
- 108091008760 retinoic acid receptors γ Proteins 0.000 title description 7
- 239000002464 receptor antagonist Substances 0.000 title description 3
- 229940044551 receptor antagonist Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 128
- 125000000217 alkyl group Chemical group 0.000 claims description 64
- 125000004432 carbon atom Chemical group C* 0.000 claims description 56
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000005037 alkyl phenyl group Chemical group 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 8
- 125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- IXQYPXRYRSEMAA-UHFFFAOYSA-N n-(1,3-diphenylprop-2-enylidene)hydroxylamine Chemical group C=1C=CC=CC=1C(=NO)C=CC1=CC=CC=C1 IXQYPXRYRSEMAA-UHFFFAOYSA-N 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000005557 antagonist Substances 0.000 abstract description 23
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
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- QSUJAUYJBJRLKV-UHFFFAOYSA-M tetraethylazanium;fluoride Chemical compound [F-].CC[N+](CC)(CC)CC QSUJAUYJBJRLKV-UHFFFAOYSA-M 0.000 description 6
- 230000001225 therapeutic effect Effects 0.000 description 6
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 5
- HMKLUDGNSIPSRI-XWWHQJGMSA-N 4-[(z)-3-[3,3-dimethyl-1-(4-methylphenyl)inden-5-yl]-3-hydroxyiminoprop-1-enyl]-3-fluorobenzoic acid Chemical compound C1=CC(C)=CC=C1C1=CC(C)(C)C2=CC(C(\C=C/C=3C(=CC(=CC=3)C(O)=O)F)=NO)=CC=C12 HMKLUDGNSIPSRI-XWWHQJGMSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
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- FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 description 5
- SEVSMVUOKAMPDO-UHFFFAOYSA-N para-Acetoxybenzaldehyde Natural products CC(=O)OC1=CC=C(C=O)C=C1 SEVSMVUOKAMPDO-UHFFFAOYSA-N 0.000 description 5
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- CFMGPKZYEUOERS-UHFFFAOYSA-N methyl 2-fluoro-4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1F CFMGPKZYEUOERS-UHFFFAOYSA-N 0.000 description 1
- UVSBCUAQEZINCQ-UHFFFAOYSA-N methyl 3-formylbenzoate Chemical compound COC(=O)C1=CC=CC(C=O)=C1 UVSBCUAQEZINCQ-UHFFFAOYSA-N 0.000 description 1
- KDPOOUQFAUOHHX-UHFFFAOYSA-N methyl 5-formylfuran-2-carboxylate Chemical compound COC(=O)C1=CC=C(C=O)O1 KDPOOUQFAUOHHX-UHFFFAOYSA-N 0.000 description 1
- RKSNUGDDGDFSRP-UHFFFAOYSA-N methyl 5-formylfuran-3-carboxylate Chemical compound COC(=O)C1=COC(C=O)=C1 RKSNUGDDGDFSRP-UHFFFAOYSA-N 0.000 description 1
- APNKWEPRZUSZCJ-UHFFFAOYSA-N methyl 5-formylthiophene-2-carboxylate Chemical compound COC(=O)C1=CC=C(C=O)S1 APNKWEPRZUSZCJ-UHFFFAOYSA-N 0.000 description 1
- GNXNZRYWBFMVHK-UHFFFAOYSA-N methyl 5-formylthiophene-3-carboxylate Chemical compound COC(=O)C1=CSC(C=O)=C1 GNXNZRYWBFMVHK-UHFFFAOYSA-N 0.000 description 1
- CERBENZCBVYKEF-UHFFFAOYSA-N methyl 6-formylpyridine-2-carboxylate Chemical compound COC(=O)C1=CC=CC(C=O)=N1 CERBENZCBVYKEF-UHFFFAOYSA-N 0.000 description 1
- BZOWIADSJYMJJJ-UHFFFAOYSA-N methyl 6-formylpyridine-3-carboxylate Chemical compound COC(=O)C1=CC=C(C=O)N=C1 BZOWIADSJYMJJJ-UHFFFAOYSA-N 0.000 description 1
- 231100000961 musculoskeletal toxicity Toxicity 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000159 protein binding assay Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 108010079850 retinoic acid receptor beta Proteins 0.000 description 1
- 108091008726 retinoic acid receptors α Proteins 0.000 description 1
- 108091008761 retinoic acid receptors β Proteins 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000003319 supportive effect Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000005076 thiochromenes Chemical class 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 231100000027 toxicology Toxicity 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 125000005270 trialkylamine group Chemical group 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 150000002266 vitamin A derivatives Chemical class 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- 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
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- 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
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pain & Pain Management (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Physical Education & Sports Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrane Compounds (AREA)
- Quinoline Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53283503P | 2003-12-26 | 2003-12-26 | |
| PCT/US2004/042892 WO2005066115A2 (en) | 2003-12-26 | 2004-12-21 | Disubstituted chalcone oximes having rarϝ retinoid receptor antagonist activity |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007518719A true JP2007518719A (ja) | 2007-07-12 |
| JP2007518719A5 JP2007518719A5 (https=) | 2007-12-13 |
Family
ID=34748824
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006547254A Pending JP2007518719A (ja) | 2003-12-26 | 2004-12-21 | ＲＡＲγレチノイド受容体アンタゴニスト活性を有する二置換カルコンオキシム |
Country Status (8)
| Country | Link |
|---|---|
| US (2) | US7253319B2 (https=) |
| EP (1) | EP1701934B1 (https=) |
| JP (1) | JP2007518719A (https=) |
| AT (1) | ATE423761T1 (https=) |
| CA (1) | CA2551294A1 (https=) |
| DE (1) | DE602004019685D1 (https=) |
| MX (1) | MXPA06007255A (https=) |
| WO (1) | WO2005066115A2 (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007517037A (ja) * | 2003-12-30 | 2007-06-28 | アラーガン インコーポレイテッド | ＲＡＲγレチノイド受容体の選択的アゴニストとしての二置換カルコンオキシム |
| WO2010092771A1 (ja) * | 2009-02-10 | 2010-08-19 | 日本曹達株式会社 | 含窒素化合物および有害生物防除剤 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101481352A (zh) | 2008-01-10 | 2009-07-15 | 上海恒瑞医药有限公司 | 双环取代吡唑酮偶氮类衍生物、其制备方法及其在医药上的应用 |
| CN101921232A (zh) | 2009-06-11 | 2010-12-22 | 上海恒瑞医药有限公司 | 双环取代吡唑酮偶氮类衍生物的盐,其制备方法及其在医药上的应用 |
| US9062015B2 (en) | 2009-12-14 | 2015-06-23 | Merck Patent Gmbh | Inhibitors of sphingosine kinase |
| AU2010341229A1 (en) | 2009-12-17 | 2012-08-02 | Merck Patent Gmbh | Sphingosine kinase inhibitors |
| US20140194517A1 (en) * | 2013-01-08 | 2014-07-10 | Io Therapeutics, Inc. | Treatment of Graft-Versus-Host Disease Disorders using RAR Antagonists |
| CN110090237B (zh) * | 2019-05-30 | 2021-05-28 | 四川农业大学 | 一种用于治疗维生素a中毒所致肝损伤和骨损伤的药物及用途 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02262552A (ja) * | 1988-12-02 | 1990-10-25 | Sanofi Sa | プロペノンオキシムエーテル類、その製造方法、並びにこれを含有する調剤組成物 |
| JP2002504887A (ja) * | 1995-09-01 | 2002-02-12 | アラーガン・セイルズ・インコーポレイテッド | ネガティブホルモン活性および／または拮抗薬活性を有するレチノイド化合物の合成と使用 |
| JP2002507204A (ja) * | 1997-06-24 | 2002-03-05 | アラーガン・セイルズ・インコーポレイテッド | ネガティブホルモン活性および／または拮抗薬活性を有するレチノイド化合物の合成と使用 |
| JP2003519103A (ja) * | 1999-12-15 | 2003-06-17 | アラーガン、インコーポレイテッド | 軟骨と骨の病状の処置におけるレチノイド受容体アンタゴニストの使用 |
| JP2003531180A (ja) * | 2000-04-20 | 2003-10-21 | アラーガン、インコーポレイテッド | 軟骨および骨の疾患の治療におけるレチノイド受容体拮抗薬または作用薬の使用 |
| JP2004532239A (ja) * | 2001-05-03 | 2004-10-21 | アラーガン、インコーポレイテッド | 高脂質血症の処置方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CA1140613A (fr) | 1979-08-22 | 1983-02-01 | Leo Jouk | Velo a cadre telescopique adaptable en velo d'appartement |
| DE69224660C5 (de) | 1991-12-18 | 2010-06-02 | The Salk Institute For Biological Studies, La Jolla | Mitteln zur modulierung von verfahren durch retinoid rezeptoren und dafür nützliche verbindungen |
| WO1994014777A1 (en) | 1992-12-28 | 1994-07-07 | Eisai Co., Ltd. | Heterocyclic carbonic acid derivatives which bind to retinoid receptors (rar) |
| US5455265A (en) | 1993-02-11 | 1995-10-03 | Allergan, Inc. | Method of treatment with compounds having selective agonist-like activity on RXR retinoid receptors |
| US5599967A (en) | 1994-12-29 | 1997-02-04 | Allergan | Acetylenes disubstituted with a 5 substituted tetrahydronaphthyl group and with an aryl of heteroaryl group having retinoid-like biological activity |
| US5958954A (en) | 1995-09-01 | 1999-09-28 | Allergan Sales, Inc. | Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities |
| US5952345A (en) * | 1995-09-01 | 1999-09-14 | Allergan Sales, Inc. | Synthesis and use of retinoid compounds having negative hormone and/or antagonist activities |
| US5723666A (en) | 1996-06-21 | 1998-03-03 | Allergan | Oxime substituted tetrahydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity |
| PT101919B (pt) | 1996-09-30 | 2000-01-31 | Hovione Sociedade Quimica Sa | Um processo para a purificacao de tohexol |
| US5739338A (en) | 1996-11-05 | 1998-04-14 | Allergan | N-aryl substituted tetrahydroquinolines having retinoid agonist, retinoid antagonist or retinoid inverse agonist type biological activity |
| US5760276A (en) | 1997-03-06 | 1998-06-02 | Allergan | Aryl-and heteroarylcyclohexenyl substituted alkenes having retinoid agonist, antagonist or inverse agonist type biological activity |
| US6037488A (en) | 1997-04-19 | 2000-03-14 | Allergan Sales, Inc. | Trisubstituted phenyl derivatives having retinoid agonist, antagonist or inverse agonist type biological activity |
| US5919970A (en) | 1997-04-24 | 1999-07-06 | Allergan Sales, Inc. | Substituted diaryl or diheteroaryl methanes, ethers and amines having retinoid agonist, antagonist or inverse agonist type biological activity |
| DE60136477D1 (de) * | 2000-10-02 | 2008-12-18 | Hoffmann La Roche | Retinoide zur behandlung von emphysem |
-
2004
- 2004-12-21 DE DE602004019685T patent/DE602004019685D1/de not_active Expired - Lifetime
- 2004-12-21 MX MXPA06007255A patent/MXPA06007255A/es active IP Right Grant
- 2004-12-21 CA CA002551294A patent/CA2551294A1/en not_active Abandoned
- 2004-12-21 AT AT04815018T patent/ATE423761T1/de not_active IP Right Cessation
- 2004-12-21 WO PCT/US2004/042892 patent/WO2005066115A2/en not_active Ceased
- 2004-12-21 JP JP2006547254A patent/JP2007518719A/ja active Pending
- 2004-12-21 EP EP04815018A patent/EP1701934B1/en not_active Expired - Lifetime
- 2004-12-23 US US11/021,471 patent/US7253319B2/en not_active Expired - Fee Related
-
2007
- 2007-06-04 US US11/810,047 patent/US7432388B2/en not_active Expired - Fee Related
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH02262552A (ja) * | 1988-12-02 | 1990-10-25 | Sanofi Sa | プロペノンオキシムエーテル類、その製造方法、並びにこれを含有する調剤組成物 |
| JP2002504887A (ja) * | 1995-09-01 | 2002-02-12 | アラーガン・セイルズ・インコーポレイテッド | ネガティブホルモン活性および／または拮抗薬活性を有するレチノイド化合物の合成と使用 |
| JP2002507204A (ja) * | 1997-06-24 | 2002-03-05 | アラーガン・セイルズ・インコーポレイテッド | ネガティブホルモン活性および／または拮抗薬活性を有するレチノイド化合物の合成と使用 |
| JP2003519103A (ja) * | 1999-12-15 | 2003-06-17 | アラーガン、インコーポレイテッド | 軟骨と骨の病状の処置におけるレチノイド受容体アンタゴニストの使用 |
| JP2003531180A (ja) * | 2000-04-20 | 2003-10-21 | アラーガン、インコーポレイテッド | 軟骨および骨の疾患の治療におけるレチノイド受容体拮抗薬または作用薬の使用 |
| JP2004532239A (ja) * | 2001-05-03 | 2004-10-21 | アラーガン、インコーポレイテッド | 高脂質血症の処置方法 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007517037A (ja) * | 2003-12-30 | 2007-06-28 | アラーガン インコーポレイテッド | ＲＡＲγレチノイド受容体の選択的アゴニストとしての二置換カルコンオキシム |
| WO2010092771A1 (ja) * | 2009-02-10 | 2010-08-19 | 日本曹達株式会社 | 含窒素化合物および有害生物防除剤 |
| US8222420B2 (en) | 2009-02-10 | 2012-07-17 | Nippon Soda Co., Ltd. | Nitrogen-containing compounds and harmful organism control agents |
Also Published As
| Publication number | Publication date |
|---|---|
| US20080097119A1 (en) | 2008-04-24 |
| DE602004019685D1 (de) | 2009-04-09 |
| WO2005066115A3 (en) | 2006-01-12 |
| ATE423761T1 (de) | 2009-03-15 |
| MXPA06007255A (es) | 2006-08-18 |
| WO2005066115A2 (en) | 2005-07-21 |
| CA2551294A1 (en) | 2005-07-21 |
| WO2005066115A8 (en) | 2005-10-27 |
| EP1701934A2 (en) | 2006-09-20 |
| US7253319B2 (en) | 2007-08-07 |
| US20050165095A1 (en) | 2005-07-28 |
| US7432388B2 (en) | 2008-10-07 |
| EP1701934B1 (en) | 2009-02-25 |
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