KR20060034284A - 간 x 수용체 조절제로서의 피롤-2,5-디티온 유도체 - Google Patents
간 x 수용체 조절제로서의 피롤-2,5-디티온 유도체 Download PDFInfo
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- KR20060034284A KR20060034284A KR1020067000616A KR20067000616A KR20060034284A KR 20060034284 A KR20060034284 A KR 20060034284A KR 1020067000616 A KR1020067000616 A KR 1020067000616A KR 20067000616 A KR20067000616 A KR 20067000616A KR 20060034284 A KR20060034284 A KR 20060034284A
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- phenyl
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- DVUZQONFTJKFPV-UHFFFAOYSA-N pyrrole-2,5-dithione Chemical class S=C1NC(=S)C=C1 DVUZQONFTJKFPV-UHFFFAOYSA-N 0.000 title description 2
- 206010023025 Ischaemic hepatitis Diseases 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 277
- 238000011282 treatment Methods 0.000 claims abstract description 119
- 238000000034 method Methods 0.000 claims abstract description 82
- 102000004311 liver X receptors Human genes 0.000 claims abstract description 41
- 108090000865 liver X receptors Proteins 0.000 claims abstract description 41
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 33
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims abstract description 22
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 18
- 208000032928 Dyslipidaemia Diseases 0.000 claims abstract description 17
- 208000017170 Lipid metabolism disease Diseases 0.000 claims abstract description 15
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 13
- 230000004968 inflammatory condition Effects 0.000 claims abstract description 11
- 230000005856 abnormality Effects 0.000 claims abstract description 8
- 206010022489 Insulin Resistance Diseases 0.000 claims abstract description 7
- 150000002632 lipids Chemical class 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
- 239000012453 solvate Substances 0.000 claims description 239
- 150000003839 salts Chemical class 0.000 claims description 232
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 72
- 230000002265 prevention Effects 0.000 claims description 61
- -1 3-pyridylmethyl Chemical group 0.000 claims description 56
- 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 54
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- 235000012000 cholesterol Nutrition 0.000 claims description 26
- 239000003153 chemical reaction reagent Substances 0.000 claims description 25
- 241000282412 Homo Species 0.000 claims description 23
- 230000002829 reductive effect Effects 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 108010010234 HDL Lipoproteins Proteins 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
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- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 10
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- 238000008214 LDL Cholesterol Methods 0.000 claims description 10
- 230000033227 intestinal cholesterol absorption Effects 0.000 claims description 10
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 7
- 108010007622 LDL Lipoproteins Proteins 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
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- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
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- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
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- MOHJWUULCVHTNF-UHFFFAOYSA-N 1-[(6-aminopyridin-3-yl)methyl]-3-(4-morpholin-4-ylanilino)-4-phenylpyrrole-2,5-dithione Chemical compound C1=NC(N)=CC=C1CN1C(=S)C(C=2C=CC=CC=2)=C(NC=2C=CC(=CC=2)N2CCOCC2)C1=S MOHJWUULCVHTNF-UHFFFAOYSA-N 0.000 claims description 3
- JEJQEUJVUYOUSX-UHFFFAOYSA-N 1-[(6-aminopyridin-3-yl)methyl]-3-[4-(difluoromethoxy)anilino]-4-phenylpyrrole-2,5-dithione Chemical compound C1=NC(N)=CC=C1CN1C(=S)C(C=2C=CC=CC=2)=C(NC=2C=CC(OC(F)F)=CC=2)C1=S JEJQEUJVUYOUSX-UHFFFAOYSA-N 0.000 claims description 3
- HKOGZAJTQNVYKL-UHFFFAOYSA-N 1-[(6-aminopyridin-3-yl)methyl]-4-[4-(difluoromethoxy)anilino]-3-phenyl-5-sulfanylidenepyrrol-2-one Chemical compound C1=NC(N)=CC=C1CN1C(=S)C(NC=2C=CC(OC(F)F)=CC=2)=C(C=2C=CC=CC=2)C1=O HKOGZAJTQNVYKL-UHFFFAOYSA-N 0.000 claims description 3
- IOIWSAHJOUDSRY-UHFFFAOYSA-N 1-benzyl-3-(4-methoxyanilino)-4-phenylpyrrole-2,5-dithione Chemical compound C1=CC(OC)=CC=C1NC(C1=S)=C(C=2C=CC=CC=2)C(=S)N1CC1=CC=CC=C1 IOIWSAHJOUDSRY-UHFFFAOYSA-N 0.000 claims description 3
- LTTHEZOLSVUPKW-UHFFFAOYSA-N 1-benzyl-4-(4-methoxyanilino)-3-phenyl-5-sulfanylidenepyrrol-2-one Chemical compound C1=CC(OC)=CC=C1NC(C1=S)=C(C=2C=CC=CC=2)C(=O)N1CC1=CC=CC=C1 LTTHEZOLSVUPKW-UHFFFAOYSA-N 0.000 claims description 3
- YRKWCHDWFBAZKM-UHFFFAOYSA-N 1-butyl-3-(4-methoxyanilino)-4-phenylpyrrole-2,5-dithione Chemical compound C=1C=CC=CC=1C=1C(=S)N(CCCC)C(=S)C=1NC1=CC=C(OC)C=C1 YRKWCHDWFBAZKM-UHFFFAOYSA-N 0.000 claims description 3
- SNZKVZCTAGKILF-UHFFFAOYSA-N 1-butyl-4-(4-methoxyanilino)-3-phenyl-5-sulfanylidenepyrrol-2-one Chemical compound S=C1N(CCCC)C(=O)C(C=2C=CC=CC=2)=C1NC1=CC=C(OC)C=C1 SNZKVZCTAGKILF-UHFFFAOYSA-N 0.000 claims description 3
- BYRPUFZFUOVSDM-UHFFFAOYSA-N 1-ethyl-3-(4-methoxyanilino)-4-phenylpyrrole-2,5-dithione Chemical compound C=1C=CC=CC=1C=1C(=S)N(CC)C(=S)C=1NC1=CC=C(OC)C=C1 BYRPUFZFUOVSDM-UHFFFAOYSA-N 0.000 claims description 3
- SQUXAIADYPVBAH-UHFFFAOYSA-N 1-ethyl-4-(4-methoxyanilino)-3-phenyl-5-sulfanylidenepyrrol-2-one Chemical compound S=C1N(CC)C(=O)C(C=2C=CC=CC=2)=C1NC1=CC=C(OC)C=C1 SQUXAIADYPVBAH-UHFFFAOYSA-N 0.000 claims description 3
- OYVJQJGUBFXSKH-UHFFFAOYSA-N 3-(4-methoxyanilino)-1-(2-methoxyethyl)-4-phenylpyrrole-2,5-dithione Chemical compound C=1C=CC=CC=1C=1C(=S)N(CCOC)C(=S)C=1NC1=CC=C(OC)C=C1 OYVJQJGUBFXSKH-UHFFFAOYSA-N 0.000 claims description 3
- ZEJARFJOUMEMPC-UHFFFAOYSA-N 3-(4-methoxyanilino)-1-methyl-4-phenylpyrrole-2,5-dithione Chemical compound C1=CC(OC)=CC=C1NC1=C(C=2C=CC=CC=2)C(=S)N(C)C1=S ZEJARFJOUMEMPC-UHFFFAOYSA-N 0.000 claims description 3
- YZOJWRMGECTRBU-UHFFFAOYSA-N 3-(4-methoxyanilino)-4-phenyl-1-(2,2,2-trifluoroethyl)pyrrole-2,5-dithione Chemical compound C1=CC(OC)=CC=C1NC1=C(C=2C=CC=CC=2)C(=S)N(CC(F)(F)F)C1=S YZOJWRMGECTRBU-UHFFFAOYSA-N 0.000 claims description 3
- FVYSXHCRUKAQCM-UHFFFAOYSA-N 3-(4-methoxyanilino)-4-phenyl-1-(pyridin-3-ylmethyl)pyrrole-2,5-dithione Chemical compound C1=CC(OC)=CC=C1NC(C1=S)=C(C=2C=CC=CC=2)C(=S)N1CC1=CC=CN=C1 FVYSXHCRUKAQCM-UHFFFAOYSA-N 0.000 claims description 3
- QDYXCIWVXFXUMP-UHFFFAOYSA-N 3-(4-methoxyanilino)-4-phenyl-1-(pyridin-4-ylmethyl)pyrrole-2,5-dithione Chemical compound C1=CC(OC)=CC=C1NC(C1=S)=C(C=2C=CC=CC=2)C(=S)N1CC1=CC=NC=C1 QDYXCIWVXFXUMP-UHFFFAOYSA-N 0.000 claims description 3
- LWQZGNPYPZVZLJ-UHFFFAOYSA-N 4-(4-methoxyanilino)-1-(2-methoxyethyl)-3-phenyl-5-sulfanylidenepyrrol-2-one Chemical compound S=C1N(CCOC)C(=O)C(C=2C=CC=CC=2)=C1NC1=CC=C(OC)C=C1 LWQZGNPYPZVZLJ-UHFFFAOYSA-N 0.000 claims description 3
- IJRRWYZJKFXOMW-UHFFFAOYSA-N 4-(4-methoxyanilino)-1-methyl-3-phenyl-5-sulfanylidenepyrrol-2-one Chemical compound C1=CC(OC)=CC=C1NC1=C(C=2C=CC=CC=2)C(=O)N(C)C1=S IJRRWYZJKFXOMW-UHFFFAOYSA-N 0.000 claims description 3
- XNIAFQVGGFMFMX-UHFFFAOYSA-N 4-(4-methoxyanilino)-3-phenyl-1-(pyridin-3-ylmethyl)-5-sulfanylidenepyrrol-2-one Chemical compound C1=CC(OC)=CC=C1NC(C1=S)=C(C=2C=CC=CC=2)C(=O)N1CC1=CC=CN=C1 XNIAFQVGGFMFMX-UHFFFAOYSA-N 0.000 claims description 3
- MQFQGAMIOKBKSC-UHFFFAOYSA-N 4-(4-methoxyanilino)-3-phenyl-1-(pyridin-4-ylmethyl)-5-sulfanylidenepyrrol-2-one Chemical compound C1=CC(OC)=CC=C1NC(C1=S)=C(C=2C=CC=CC=2)C(=O)N1CC1=CC=NC=C1 MQFQGAMIOKBKSC-UHFFFAOYSA-N 0.000 claims description 3
- CATPDSIFGQYWIV-UHFFFAOYSA-N 4-(4-methoxyanilino)-3-phenyl-5-sulfanylidene-1-(2,2,2-trifluoroethyl)pyrrol-2-one Chemical compound C1=CC(OC)=CC=C1NC1=C(C=2C=CC=CC=2)C(=O)N(CC(F)(F)F)C1=S CATPDSIFGQYWIV-UHFFFAOYSA-N 0.000 claims description 3
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- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 2
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
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- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
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- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 229960005187 telmisartan Drugs 0.000 description 1
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- JIXSLWMKQJMSGD-UHFFFAOYSA-N tert-butyl n-[5-[(3-chloro-2,5-dioxo-4-phenylpyrrol-1-yl)methyl]pyridin-2-yl]carbamate Chemical compound C1=NC(NC(=O)OC(C)(C)C)=CC=C1CN1C(=O)C(C=2C=CC=CC=2)=C(Cl)C1=O JIXSLWMKQJMSGD-UHFFFAOYSA-N 0.000 description 1
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- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
-
- 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
- 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
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
-
- 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/36—Oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
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|---|---|---|---|
| GBGB0316237.7A GB0316237D0 (en) | 2003-07-11 | 2003-07-11 | Therapeutic agents |
| GB0316237.7 | 2003-07-11 |
Publications (1)
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|---|---|
| KR20060034284A true KR20060034284A (ko) | 2006-04-21 |
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| US (1) | US20060189663A1 (enExample) |
| EP (1) | EP1646625B1 (enExample) |
| JP (1) | JP2007521313A (enExample) |
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| AT (1) | ATE399776T1 (enExample) |
| AU (1) | AU2004256000B2 (enExample) |
| BR (1) | BRPI0412479A (enExample) |
| CA (1) | CA2532068A1 (enExample) |
| CO (1) | CO5640134A2 (enExample) |
| DE (1) | DE602004014772D1 (enExample) |
| ES (1) | ES2308205T3 (enExample) |
| GB (1) | GB0316237D0 (enExample) |
| IL (1) | IL172759A0 (enExample) |
| IS (1) | IS8291A (enExample) |
| MX (1) | MXPA06000447A (enExample) |
| NO (1) | NO20060080L (enExample) |
| RU (1) | RU2006102129A (enExample) |
| SA (1) | SA04250203B1 (enExample) |
| TW (1) | TW200507836A (enExample) |
| UA (1) | UA82108C2 (enExample) |
| UY (1) | UY28407A1 (enExample) |
| WO (1) | WO2005005416A1 (enExample) |
| ZA (1) | ZA200600229B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200001225U (ko) | 2018-12-04 | 2020-06-12 | 박규환 | 조립식 계단장치를 위한 발판 |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US7582629B2 (en) | 2005-01-10 | 2009-09-01 | Astrazeneca Ab | Derivatives of isothiazol-3(2H)-one 1,1-dioxides as liver X receptor modulators |
| SE0500058D0 (sv) * | 2005-01-10 | 2005-01-10 | Astrazeneca Ab | Therapeutic agents 5 |
| SE0500055D0 (sv) | 2005-01-10 | 2005-01-10 | Astrazeneca Ab | Therapeutic agents 3 |
| WO2007002654A2 (en) * | 2005-06-28 | 2007-01-04 | Daiichi Sankyo Company, Limited. | Lxr ligand testing method |
| EP2069359B1 (en) | 2006-08-21 | 2014-11-12 | Genentech, Inc. | Aza-benzothiophenyl compounds and methods of use |
| US20100056444A1 (en) | 2006-10-12 | 2010-03-04 | Sven Martin Jacobson | Treatment of Alzheimer's Disease Using Compounds that Reduce the Activity of Non Selective Ca Activated ATP- Sensitive Cation Channels Regulated by SUR1 Receptors |
| US10004703B2 (en) | 2006-10-12 | 2018-06-26 | Biogen Chesapeake Llc | Treatment of alzheimer's disease using compounds that reduce the activity of non-selective CA++ activated ATP-sensitive cation channels regulated by SUR1 channels |
| US20100143270A1 (en) * | 2007-02-21 | 2010-06-10 | University Of Louisville Research Foubdation | Therapeutic cotinine compositions |
| WO2009073711A1 (en) | 2007-12-04 | 2009-06-11 | Remedy Pharmaceuticals, Inc. | Improved formulations and methods for lyophilization and lyophilates provided thereby |
| WO2009097443A2 (en) * | 2008-01-29 | 2009-08-06 | Remedy Pharmaceuticals, Inc. | Liquid formulations of compounds active at sulfonylurea receptors |
| CA2727252A1 (en) | 2008-07-01 | 2010-01-07 | Genentech, Inc. | Isoindolone derivatives as mek kinase inhibitors and methods of use |
| PE20110570A1 (es) | 2008-07-01 | 2011-08-26 | Genentech Inc | Heterociclos biciclicos sustituidos |
| US20130274212A1 (en) | 2010-09-07 | 2013-10-17 | Snu R&Db Foundation | Sesterterpene Compounds and Use Thereof |
| US10669296B2 (en) | 2014-01-10 | 2020-06-02 | Rgenix, Inc. | LXR agonists and uses thereof |
| CN109069461A (zh) | 2016-01-11 | 2018-12-21 | 洛克菲勒大学 | 与髓源性抑制细胞相关的病症的治疗方法 |
| EP3713575A4 (en) | 2017-11-21 | 2021-08-25 | Rgenix, Inc. | POLYMORPHS AND THEIR USES |
| HUE067466T2 (hu) | 2019-12-13 | 2024-10-28 | Inspirna Inc | Fémsók és alkalmazásuk |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE69922526T2 (de) * | 1998-10-08 | 2005-06-02 | Smithkline Beecham Plc, Brentford | 3-(3-chloro-4-hydroxyphenylamino)-4-(2-nitrophenyl)-1h-pyrrol-2,5-dion als glykogen synthase kinase-3 inhibitor (gsk-3) |
| CA2377999A1 (en) * | 1999-07-08 | 2001-01-18 | Tularik Inc | Compositions and methods for raising hdl cholesterol levels |
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2003
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2004
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- 2004-07-08 BR BRPI0412479-0A patent/BRPI0412479A/pt not_active IP Right Cessation
- 2004-07-08 JP JP2006520139A patent/JP2007521313A/ja not_active Withdrawn
- 2004-07-08 CA CA002532068A patent/CA2532068A1/en not_active Abandoned
- 2004-07-08 AT AT04749151T patent/ATE399776T1/de not_active IP Right Cessation
- 2004-07-08 EP EP04749151A patent/EP1646625B1/en not_active Expired - Lifetime
- 2004-07-08 MX MXPA06000447A patent/MXPA06000447A/es not_active Application Discontinuation
- 2004-07-08 US US10/563,676 patent/US20060189663A1/en not_active Abandoned
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- 2004-08-07 UA UAA200600270A patent/UA82108C2/uk unknown
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| Publication number | Priority date | Publication date | Assignee | Title |
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| KR20200001225U (ko) | 2018-12-04 | 2020-06-12 | 박규환 | 조립식 계단장치를 위한 발판 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2532068A1 (en) | 2005-01-20 |
| ES2308205T3 (es) | 2008-12-01 |
| ZA200600229B (en) | 2007-04-25 |
| UY28407A1 (es) | 2005-02-28 |
| SA04250203B1 (ar) | 2008-02-25 |
| CO5640134A2 (es) | 2006-05-31 |
| EP1646625B1 (en) | 2008-07-02 |
| DE602004014772D1 (de) | 2008-08-14 |
| NO20060080L (no) | 2006-02-08 |
| AR045720A1 (es) | 2005-11-09 |
| HK1088318A1 (en) | 2006-11-03 |
| EP1646625A1 (en) | 2006-04-19 |
| BRPI0412479A (pt) | 2006-09-19 |
| AU2004256000B2 (en) | 2007-07-26 |
| CN100478340C (zh) | 2009-04-15 |
| MXPA06000447A (es) | 2006-04-07 |
| WO2005005416A1 (en) | 2005-01-20 |
| GB0316237D0 (en) | 2003-08-13 |
| AU2004256000A1 (en) | 2005-01-20 |
| JP2007521313A (ja) | 2007-08-02 |
| IL172759A0 (en) | 2006-04-10 |
| TW200507836A (en) | 2005-03-01 |
| US20060189663A1 (en) | 2006-08-24 |
| CN1820003A (zh) | 2006-08-16 |
| IS8291A (is) | 2006-02-09 |
| UA82108C2 (uk) | 2008-03-11 |
| RU2006102129A (ru) | 2006-08-27 |
| ATE399776T1 (de) | 2008-07-15 |
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