ZA200600222B - Pyrrole-2,5-dione derivatives as Liver X receptor modulars - Google Patents
Pyrrole-2,5-dione derivatives as Liver X receptor modulars Download PDFInfo
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- ZA200600222B ZA200600222B ZA200600222A ZA200600222A ZA200600222B ZA 200600222 B ZA200600222 B ZA 200600222B ZA 200600222 A ZA200600222 A ZA 200600222A ZA 200600222 A ZA200600222 A ZA 200600222A ZA 200600222 B ZA200600222 B ZA 200600222B
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- South Africa
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- composition
- substance
- phenyl
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- 102000004311 liver X receptors Human genes 0.000 title description 22
- 108090000865 liver X receptors Proteins 0.000 title description 22
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical class O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 236
- 150000003839 salts Chemical class 0.000 claims description 187
- 239000012453 solvate Substances 0.000 claims description 186
- -1 2- methylthioethyl Chemical group 0.000 claims description 96
- 238000000034 method Methods 0.000 claims description 94
- 238000011282 treatment Methods 0.000 claims description 90
- 239000000203 mixture Substances 0.000 claims description 59
- 239000000126 substance Substances 0.000 claims description 54
- 238000011321 prophylaxis Methods 0.000 claims description 52
- 239000003814 drug Substances 0.000 claims description 46
- 241000124008 Mammalia Species 0.000 claims description 43
- 238000004519 manufacturing process Methods 0.000 claims description 33
- 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
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 201000001320 Atherosclerosis Diseases 0.000 claims description 25
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 23
- 230000003247 decreasing effect Effects 0.000 claims description 21
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 16
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 14
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 14
- 235000012000 cholesterol Nutrition 0.000 claims description 13
- 108010010234 HDL Lipoproteins Proteins 0.000 claims description 12
- 230000033227 intestinal cholesterol absorption Effects 0.000 claims description 12
- 230000004141 reverse cholesterol transport Effects 0.000 claims description 12
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 10
- 206010061218 Inflammation Diseases 0.000 claims description 10
- 201000010099 disease Diseases 0.000 claims description 10
- 230000004054 inflammatory process Effects 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 229940124597 therapeutic agent Drugs 0.000 claims description 10
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 9
- 208000024827 Alzheimer disease Diseases 0.000 claims description 9
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 8
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 8
- 108010028554 LDL Cholesterol Proteins 0.000 claims description 8
- 238000008214 LDL Cholesterol Methods 0.000 claims description 8
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- 238000011161 development Methods 0.000 claims description 8
- 230000004968 inflammatory condition Effects 0.000 claims description 8
- 235000020824 obesity Nutrition 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- 108010023302 HDL Cholesterol Proteins 0.000 claims description 7
- 206010022489 Insulin Resistance Diseases 0.000 claims description 7
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 7
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 6
- 206010020772 Hypertension Diseases 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 6
- 208000017170 Lipid metabolism disease Diseases 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 150000002632 lipids Chemical class 0.000 claims description 5
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 4
- 239000002671 adjuvant Substances 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
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- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- IJDRKXJGEDBBKZ-UHFFFAOYSA-N 3-(4-methoxyanilino)-1-(2-methoxyethyl)-4-phenylpyrrole-2,5-dione Chemical compound C=1C=CC=CC=1C=1C(=O)N(CCOC)C(=O)C=1NC1=CC=C(OC)C=C1 IJDRKXJGEDBBKZ-UHFFFAOYSA-N 0.000 claims description 2
- LGKWEWTVEPDUAV-UHFFFAOYSA-N 3-(4-methoxyanilino)-1-(3-methoxypropyl)-4-phenylpyrrole-2,5-dione Chemical compound C=1C=CC=CC=1C=1C(=O)N(CCCOC)C(=O)C=1NC1=CC=C(OC)C=C1 LGKWEWTVEPDUAV-UHFFFAOYSA-N 0.000 claims description 2
- WMNVVLNVJBKEMR-UHFFFAOYSA-N 3-(4-methoxyanilino)-4-phenyl-1-(pyridin-2-ylmethyl)pyrrole-2,5-dione Chemical compound C1=CC(OC)=CC=C1NC(C1=O)=C(C=2C=CC=CC=2)C(=O)N1CC1=CC=CC=N1 WMNVVLNVJBKEMR-UHFFFAOYSA-N 0.000 claims description 2
- BWABNEHKDRQBPP-UHFFFAOYSA-N 3-(4-methoxyanilino)-4-phenyl-1-(pyridin-4-ylmethyl)pyrrole-2,5-dione Chemical compound C1=CC(OC)=CC=C1NC(C1=O)=C(C=2C=CC=CC=2)C(=O)N1CC1=CC=NC=C1 BWABNEHKDRQBPP-UHFFFAOYSA-N 0.000 claims description 2
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 claims description 2
- UPRKUOAEQJLFMJ-UHFFFAOYSA-N C(C)(=O)C=1OC2=C(C1)C=C(C=C2)NC=2C(N(C(C2C2=CC=CC=C2)=O)CC=2C=NC=CC2)=O.N2(CCOCC2)C2=CC=C(C=C2)NC=2C(N(C(C2C2=CC=CC=C2)=O)CC=2C=NC=CC2)=O Chemical compound C(C)(=O)C=1OC2=C(C1)C=C(C=C2)NC=2C(N(C(C2C2=CC=CC=C2)=O)CC=2C=NC=CC2)=O.N2(CCOCC2)C2=CC=C(C=C2)NC=2C(N(C(C2C2=CC=CC=C2)=O)CC=2C=NC=CC2)=O UPRKUOAEQJLFMJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000005604 azodicarboxylate group Chemical group 0.000 claims description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- FAMRKDQNMBBFBR-BQYQJAHWSA-N diethyl azodicarboxylate Substances CCOC(=O)\N=N\C(=O)OCC FAMRKDQNMBBFBR-BQYQJAHWSA-N 0.000 claims description 2
- FAMRKDQNMBBFBR-UHFFFAOYSA-N ethyl n-ethoxycarbonyliminocarbamate Chemical compound CCOC(=O)N=NC(=O)OCC FAMRKDQNMBBFBR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- UGTDRLZDYHDNHS-UHFFFAOYSA-N methyl 4-[[3-(4-methoxyanilino)-2,5-dioxo-4-phenylpyrrol-1-yl]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1CN1C(=O)C(C=2C=CC=CC=2)=C(NC=2C=CC(OC)=CC=2)C1=O UGTDRLZDYHDNHS-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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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
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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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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/04—Anorexiants; Antiobesity agents
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- 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
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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
- 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
-
- 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
- C07D207/444—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 having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/456—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 having two doubly-bound oxygen atoms directly attached in positions 2 and 5 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 other ring carbon 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms 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)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Hematology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurosurgery (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (1)
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| ZA200600222B true ZA200600222B (en) | 2007-04-25 |
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| ZA200600222A ZA200600222B (en) | 2003-07-11 | 2006-01-10 | Pyrrole-2,5-dione derivatives as Liver X receptor modulars |
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| UY (1) | UY28408A1 (enExample) |
| WO (1) | WO2005005417A1 (enExample) |
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| ATE513823T1 (de) * | 2004-08-17 | 2011-07-15 | Simpson Biotech Co Ltd | Mischung und verbindungen von mycelien von antrodia camphorata und deren verwendung |
| US7505238B2 (en) * | 2005-01-07 | 2009-03-17 | Agnes Neves Woo | ESD configuration for low parasitic capacitance I/O |
| US7582629B2 (en) | 2005-01-10 | 2009-09-01 | Astrazeneca Ab | Derivatives of isothiazol-3(2H)-one 1,1-dioxides as liver X receptor modulators |
| SE0500055D0 (sv) | 2005-01-10 | 2005-01-10 | Astrazeneca Ab | Therapeutic agents 3 |
| MX2008013477A (es) * | 2006-04-28 | 2008-10-29 | Esteve Labor Dr | Compuestos biciclicos de tetrahidropirrol. |
| EP2069359B1 (en) | 2006-08-21 | 2014-11-12 | Genentech, Inc. | Aza-benzothiophenyl compounds and methods of use |
| CN101456863B (zh) * | 2007-12-14 | 2012-04-25 | 华北制药集团新药研究开发有限责任公司 | Lxr激动剂及其制备方法和用途 |
| PE20110570A1 (es) | 2008-07-01 | 2011-08-26 | Genentech Inc | Heterociclos biciclicos sustituidos |
| CA2727252A1 (en) | 2008-07-01 | 2010-01-07 | Genentech, Inc. | Isoindolone derivatives as mek kinase inhibitors and methods of use |
| US20130274212A1 (en) | 2010-09-07 | 2013-10-17 | Snu R&Db Foundation | Sesterterpene Compounds and Use Thereof |
| AU2011336970A1 (en) | 2010-12-03 | 2013-07-11 | Allergan, Inc. | Novel oxime derivatives as sphingosine 1-phosphate (S1P) receptor modulators |
| EP2646018B1 (en) | 2010-12-03 | 2014-10-22 | Allergan, Inc. | Novel oxime azetidine derivatives as sphingosine 1-phosphate (s1p) receptor modulators |
| 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 |
| US11753374B2 (en) * | 2020-11-18 | 2023-09-12 | Southern Reserach Institute | Compounds for the treatment of acute and chronic kidney disease |
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| AU4929999A (en) | 1998-07-30 | 2000-02-21 | Japan Tobacco Inc. | Disubstituted maleimide compounds and medicinal utilization thereof |
| 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 |
| WO2001013916A1 (en) | 1999-08-20 | 2001-03-01 | Sagami Chemical Research Center | Drugs inhibiting cell death |
| GB0008264D0 (en) | 2000-04-04 | 2000-05-24 | Smithkline Beecham Plc | Novel method and compounds |
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Also Published As
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| US7432288B2 (en) | 2008-10-07 |
| UA82109C2 (uk) | 2008-03-11 |
| US20060235015A1 (en) | 2006-10-19 |
| SA04250204B1 (ar) | 2008-03-23 |
| IS8293A (is) | 2006-02-09 |
| IL172760A0 (en) | 2006-04-10 |
| WO2005005417A1 (en) | 2005-01-20 |
| CA2532056A1 (en) | 2005-01-20 |
| AR045721A1 (es) | 2005-11-09 |
| AU2004255999B2 (en) | 2007-08-02 |
| GB0316232D0 (en) | 2003-08-13 |
| MY135821A (en) | 2008-07-31 |
| KR20060035748A (ko) | 2006-04-26 |
| EP1646626B1 (en) | 2008-07-02 |
| JP2007521312A (ja) | 2007-08-02 |
| RU2006102130A (ru) | 2007-08-20 |
| BRPI0412472A (pt) | 2006-09-19 |
| AU2004255999A1 (en) | 2005-01-20 |
| MXPA06000414A (es) | 2006-03-17 |
| ATE399777T1 (de) | 2008-07-15 |
| ES2308204T3 (es) | 2008-12-01 |
| HK1088320A1 (en) | 2006-11-03 |
| NO20060081L (no) | 2006-02-08 |
| EP1646626A1 (en) | 2006-04-19 |
| TW200503691A (en) | 2005-02-01 |
| CN1823061A (zh) | 2006-08-23 |
| DE602004014773D1 (de) | 2008-08-14 |
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