JP2005521705A - 化合物および方法 - Google Patents
化合物および方法 Download PDFInfo
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- JP2005521705A JP2005521705A JP2003579735A JP2003579735A JP2005521705A JP 2005521705 A JP2005521705 A JP 2005521705A JP 2003579735 A JP2003579735 A JP 2003579735A JP 2003579735 A JP2003579735 A JP 2003579735A JP 2005521705 A JP2005521705 A JP 2005521705A
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- JP
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- Prior art keywords
- alkyl
- amino
- ethyl
- het
- unsubstituted
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 186
- 238000000034 method Methods 0.000 title claims description 68
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 239000012453 solvate Substances 0.000 claims abstract description 27
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 134
- -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 75
- 125000005843 halogen group Chemical group 0.000 claims description 74
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 72
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 65
- 239000000203 mixture Substances 0.000 claims description 64
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 125000001424 substituent group Chemical group 0.000 claims description 47
- 102000004311 liver X receptors Human genes 0.000 claims description 45
- 108090000865 liver X receptors Proteins 0.000 claims description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 30
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 26
- 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 claims description 26
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
- 229910052799 carbon Inorganic materials 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 201000010099 disease Diseases 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 238000011282 treatment Methods 0.000 claims description 19
- 125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims description 18
- HBEDSQVIWPRPAY-UHFFFAOYSA-N 2,3-dihydrobenzofuran Chemical compound C1=CC=C2OCCC2=C1 HBEDSQVIWPRPAY-UHFFFAOYSA-N 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 230000001404 mediated effect Effects 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
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- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 206010061218 Inflammation Diseases 0.000 claims description 11
- 230000004054 inflammatory process Effects 0.000 claims description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 230000002265 prevention Effects 0.000 claims description 10
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 9
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 9
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 9
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 7
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 7
- 230000001906 cholesterol absorption Effects 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
- 201000001320 Atherosclerosis Diseases 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- LDUSWUXHYFJPSN-UHFFFAOYSA-N 2-[2-[3-[(2,4-dimethoxyphenyl)methyl-(2,2-diphenylethyl)amino]propyl]-1-benzofuran-6-yl]ethanol Chemical compound COC1=CC(OC)=CC=C1CN(CC(C=1C=CC=CC=1)C=1C=CC=CC=1)CCCC1=CC2=CC=C(CCO)C=C2O1 LDUSWUXHYFJPSN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 1
- 239000000556 agonist Substances 0.000 abstract description 8
- 239000000126 substance Substances 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 59
- 239000000243 solution Substances 0.000 description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
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- 238000009472 formulation Methods 0.000 description 25
- 229960000583 acetic acid Drugs 0.000 description 23
- 229920006395 saturated elastomer Polymers 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 150000002367 halogens Chemical group 0.000 description 19
- 239000003921 oil Substances 0.000 description 18
- 239000011734 sodium Substances 0.000 description 18
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 15
- 239000000843 powder Substances 0.000 description 15
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 239000011780 sodium chloride Substances 0.000 description 14
- 238000004440 column chromatography Methods 0.000 description 13
- 239000012043 crude product Substances 0.000 description 13
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 13
- KUNCMOAFNYLOSC-UHFFFAOYSA-N 2-chloro-3-(trifluoromethyl)benzaldehyde Chemical compound FC(F)(F)C1=CC=CC(C=O)=C1Cl KUNCMOAFNYLOSC-UHFFFAOYSA-N 0.000 description 12
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 12
- 239000000741 silica gel Substances 0.000 description 12
- 229910002027 silica gel Inorganic materials 0.000 description 12
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 11
- 108090000623 proteins and genes Proteins 0.000 description 11
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 9
- 239000012044 organic layer Substances 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 102100033616 Phospholipid-transporting ATPase ABCA1 Human genes 0.000 description 8
- 101710205202 Phospholipid-transporting ATPase ABCA1 Proteins 0.000 description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 238000003556 assay Methods 0.000 description 8
- 125000002541 furyl group Chemical group 0.000 description 8
- 125000002757 morpholinyl group Chemical group 0.000 description 8
- 150000003141 primary amines Chemical class 0.000 description 8
- 108090000765 processed proteins & peptides Proteins 0.000 description 8
- 235000018102 proteins Nutrition 0.000 description 8
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- 125000000719 pyrrolidinyl group Chemical group 0.000 description 8
- 125000000168 pyrrolyl group Chemical group 0.000 description 8
- 150000003512 tertiary amines Chemical class 0.000 description 8
- 125000000304 alkynyl group Chemical group 0.000 description 7
- 235000001014 amino acid Nutrition 0.000 description 7
- 150000001413 amino acids Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 150000004702 methyl esters Chemical class 0.000 description 7
- 230000004770 neurodegeneration Effects 0.000 description 7
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
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- 150000003335 secondary amines Chemical class 0.000 description 7
- 238000010998 test method Methods 0.000 description 7
- 125000001544 thienyl group Chemical group 0.000 description 7
- 239000003656 tris buffered saline Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- 108010010234 HDL Lipoproteins Proteins 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
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- 150000001412 amines Chemical class 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 125000002883 imidazolyl group Chemical group 0.000 description 6
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- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 5
- RXMTUVIKZRXSSM-UHFFFAOYSA-N 2,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(CN)C1=CC=CC=C1 RXMTUVIKZRXSSM-UHFFFAOYSA-N 0.000 description 5
- WEBVDBDZSOJGPB-UHFFFAOYSA-N 2,3-dihydro-1-benzofuran-5-carbaldehyde Chemical compound O=CC1=CC=C2OCCC2=C1 WEBVDBDZSOJGPB-UHFFFAOYSA-N 0.000 description 5
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Classifications
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
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- 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]
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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
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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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
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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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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)
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- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
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- Hematology (AREA)
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- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| US36841502P | 2002-03-27 | 2002-03-27 | |
| PCT/US2003/009039 WO2003082192A2 (en) | 2002-03-27 | 2003-03-26 | Certain pharmaceutically useful substituted aminoalkyl heterocycles |
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| EP1318976B1 (en) * | 2000-09-18 | 2004-11-24 | Glaxo Group Limited | Substituted aminopropoxyaryl derivatives useful as agonists for lxr |
| WO2003082802A1 (en) | 2002-03-27 | 2003-10-09 | Smithkline Beecham Corporation | Acid and ester compounds and methods of using the same |
| EP1511483A4 (en) * | 2002-03-27 | 2009-03-18 | Smithkline Beecham Corp | PROCESSING METHODS USING LXR MODULATORS |
| JP2006512280A (ja) | 2002-03-27 | 2006-04-13 | スミスクライン・ビーチャム・コーポレイション | 化合物および方法 |
| EP1497270A4 (en) | 2002-03-27 | 2006-01-04 | Smithkline Beecham Corp | AMID COMPOUNDS AND METHOD FOR THEIR USE |
| AU2003291719A1 (en) * | 2002-11-06 | 2004-06-03 | Schering Corporation | Cholesterol absorptions inhibitors for the treatment of autoimmune disorders |
| FR2869904B1 (fr) | 2004-05-07 | 2006-07-28 | Fournier S A Sa Lab | Modulateurs des recepteurs lxr |
| IL166149A0 (en) * | 2005-01-05 | 2006-01-15 | Hadasit Med Res Service | Use of ezetimibe and amiodarone in protection against beta-amyloid neurotoxicity |
| JP5159633B2 (ja) | 2006-11-30 | 2013-03-06 | 興和株式会社 | 置換カルビノール化合物 |
| WO2009107387A1 (ja) | 2008-02-29 | 2009-09-03 | 興和株式会社 | ２－オキソクロメン誘導体 |
| WO2009122707A1 (ja) | 2008-03-31 | 2009-10-08 | 興和株式会社 | １，３－ジヒドロイソベンゾフラン誘導体 |
| WO2009133692A1 (ja) | 2008-04-30 | 2009-11-05 | 興和株式会社 | キノリン化合物 |
| CN102105452A (zh) | 2008-05-29 | 2011-06-22 | 兴和株式会社 | 具有环状连接基的取代甲醇化合物 |
| BRPI1016232A2 (pt) | 2009-04-29 | 2023-04-11 | Kowa Co | Composto de carbinol, medicamento, regulador de lxr, composição farmacêutica, método para prevenir e/ou tratar doenças, e, uso do composto de carbinol |
| US20130274212A1 (en) | 2010-09-07 | 2013-10-17 | Snu R&Db Foundation | Sesterterpene Compounds and Use Thereof |
| CN110494415A (zh) | 2017-03-03 | 2019-11-22 | 睿治尼斯公司 | 具有改善的稳定性的制剂 |
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| WO1989003819A1 (fr) | 1987-10-20 | 1989-05-05 | Otsuka Pharmaceutical Co., Ltd. | Derives d'acide phenylcarboxylique |
| US20030153541A1 (en) | 1997-10-31 | 2003-08-14 | Robert Dudley | Novel anticholesterol compositions and method for using same |
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| WO2001060818A1 (en) * | 2000-02-14 | 2001-08-23 | Tularik Inc. | Lxr modulators |
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| US7470659B2 (en) | 2001-12-07 | 2008-12-30 | The Regents Of The University Of California | Methods to increase reverse cholesterol transport in the retinal pigment epithelium (RPE) and Bruch's membrane (BM) |
| US20030162758A1 (en) | 2001-12-07 | 2003-08-28 | Schwartz Daniel M. | Treatment for age-related macular degeneration (AMD) |
| US20030229062A1 (en) | 2001-12-07 | 2003-12-11 | The Regents Of The University Of California | Treatments for age-related macular degeneration (AMD) |
| JP2006512280A (ja) | 2002-03-27 | 2006-04-13 | スミスクライン・ビーチャム・コーポレイション | 化合物および方法 |
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| WO2004110368A2 (en) | 2003-06-06 | 2004-12-23 | Merck & Co., Inc. | Combination therapy for the treatment of hypertension |
| EP1646394A2 (en) | 2003-07-22 | 2006-04-19 | Glaxo Group Limited | Methods of treatment with lxr agonists |
| JP2007500158A (ja) | 2003-07-28 | 2007-01-11 | グラクソ グループ リミテッド | Ｌｘｒアゴニストを用いる炎症性腸疾患の治療方法 |
| WO2005055998A1 (en) | 2003-12-04 | 2005-06-23 | Smithkline Beecham Corporation | Methods of treatment with lxr agonists |
| SV2005001973A (es) | 2003-12-12 | 2005-11-04 | Wyeth Corp | Quinolinas utiles en el tratamiento de enfermedades cardiovasculares ref. wyth0090-504 (am101500) |
| JP2008503547A (ja) | 2004-06-24 | 2008-02-07 | ガラパゴス・ナムローゼ・フェンノートシャップ | 骨ホメオスタシスを促進させる方法及び組成物 |
| CN101119747A (zh) | 2004-07-02 | 2008-02-06 | 三共株式会社 | 组织因子产生抑制剂 |
-
2003
- 2003-03-26 AU AU2003223340A patent/AU2003223340A1/en not_active Abandoned
- 2003-03-26 JP JP2003579735A patent/JP2005521705A/ja active Pending
- 2003-03-26 WO PCT/US2003/009039 patent/WO2003082192A2/en not_active Ceased
- 2003-03-26 ES ES03719457T patent/ES2337037T3/es not_active Expired - Lifetime
- 2003-03-26 EP EP03719457A patent/EP1490047B1/en not_active Expired - Lifetime
- 2003-03-26 DE DE60330758T patent/DE60330758D1/de not_active Expired - Lifetime
- 2003-03-26 US US10/508,822 patent/US7323494B2/en not_active Expired - Lifetime
- 2003-03-26 AT AT03719457T patent/ATE453389T1/de not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005533007A (ja) * | 2002-03-27 | 2005-11-04 | スミスクライン・ビーチャム・コーポレイション | Ｌｘｒ調節因子を用いる治療方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1490047B1 (en) | 2009-12-30 |
| US20050165045A1 (en) | 2005-07-28 |
| WO2003082192A2 (en) | 2003-10-09 |
| AU2003223340A1 (en) | 2003-10-13 |
| AU2003223340A8 (en) | 2003-10-13 |
| ATE453389T1 (de) | 2010-01-15 |
| ES2337037T3 (es) | 2010-04-20 |
| US7323494B2 (en) | 2008-01-29 |
| DE60330758D1 (de) | 2010-02-11 |
| WO2003082192A3 (en) | 2003-12-18 |
| EP1490047A4 (en) | 2006-01-04 |
| EP1490047A2 (en) | 2004-12-29 |
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