ES2311179T3 - Pirazoles sustituidos como agonistas de ppar. - Google Patents
Pirazoles sustituidos como agonistas de ppar. Download PDFInfo
- Publication number
- ES2311179T3 ES2311179T3 ES04818779T ES04818779T ES2311179T3 ES 2311179 T3 ES2311179 T3 ES 2311179T3 ES 04818779 T ES04818779 T ES 04818779T ES 04818779 T ES04818779 T ES 04818779T ES 2311179 T3 ES2311179 T3 ES 2311179T3
- Authority
- ES
- Spain
- Prior art keywords
- methyl
- phenyl
- pyrazol
- amino
- carbonyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 title description 4
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 title description 4
- -1 morpholino, pyrrolidino, piperidino, thiophenyl Chemical group 0.000 claims abstract description 198
- 150000001875 compounds Chemical class 0.000 claims abstract description 138
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 52
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 150000002148 esters Chemical class 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 239000012453 solvate Substances 0.000 claims abstract description 7
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 103
- 239000002253 acid Substances 0.000 claims description 95
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 54
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 25
- 235000019260 propionic acid Nutrition 0.000 claims description 25
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 19
- 102100038831 Peroxisome proliferator-activated receptor alpha Human genes 0.000 claims description 17
- 101000741788 Homo sapiens Peroxisome proliferator-activated receptor alpha Proteins 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 15
- 201000010099 disease Diseases 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 239000000556 agonist Substances 0.000 claims description 10
- 230000001404 mediated effect Effects 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 208000032928 Dyslipidaemia Diseases 0.000 claims description 5
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- STQUOPOPURPPAC-UHFFFAOYSA-N 2-[2-chloro-6-methyl-4-[[[1-methyl-5-[4-(2-methylpropyl)phenyl]pyrazole-3-carbonyl]amino]methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=CC(CC(C)C)=CC=C1C1=CC(C(=O)NCC=2C=C(Cl)C(OC(C)(C)C(O)=O)=C(C)C=2)=NN1C STQUOPOPURPPAC-UHFFFAOYSA-N 0.000 claims description 3
- DSQDXGANBLAVCL-UHFFFAOYSA-N 2-[2-methoxy-4-[[[1-methyl-5-[4-(2-methylpropyl)phenyl]pyrazole-3-carbonyl]amino]methyl]phenoxy]-2-methylpropanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(OC)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(CC(C)C)=CC=3)=C2)=C1 DSQDXGANBLAVCL-UHFFFAOYSA-N 0.000 claims description 3
- AEXZSCUBUIJTHV-UHFFFAOYSA-N 2-[4-[[[5-(4-butylphenyl)-1-methylpyrazole-3-carbonyl]amino]methyl]-2,6-dimethylphenoxy]-2-methylpropanoic acid Chemical compound C1=CC(CCCC)=CC=C1C1=CC(C(=O)NCC=2C=C(C)C(OC(C)(C)C(O)=O)=C(C)C=2)=NN1C AEXZSCUBUIJTHV-UHFFFAOYSA-N 0.000 claims description 3
- OBVBKFWKMJVFQB-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[2-methyl-5-(3-phenylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=C(C=CC=2)C=2C=CC=CC=2)C)=C1 OBVBKFWKMJVFQB-UHFFFAOYSA-N 0.000 claims description 3
- QLMWFHGMHPPJLN-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[2-methyl-5-(4-phenylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)C)=C1 QLMWFHGMHPPJLN-UHFFFAOYSA-N 0.000 claims description 3
- 208000000103 Anorexia Nervosa Diseases 0.000 claims description 3
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- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 3
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
- 206010022489 Insulin Resistance Diseases 0.000 claims description 3
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- OMPVSODEIZVPQA-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-1-(2-methoxyethyl)pyrazole-3-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound COCCN1N=C(C(=O)NCC=2C=C(C)C(OC(C)(C)C(O)=O)=CC=2)C=C1C1=CC=C(C(C)(C)C)C=C1 OMPVSODEIZVPQA-UHFFFAOYSA-N 0.000 claims description 2
- ASNQEFKXXIMVQR-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-1-methylpyrazole-3-carbonyl]amino]methyl]-2,6-dimethylphenoxy]-2-methylpropanoic acid Chemical compound CC1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(=CC=3)C(C)(C)C)=C2)=C1 ASNQEFKXXIMVQR-UHFFFAOYSA-N 0.000 claims description 2
- HZIOXHZMCMSLJZ-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-2-(2-methoxyethyl)pyrazole-3-carbonyl]amino]methyl]-2-methylphenoxy]-2-methylpropanoic acid Chemical compound COCCN1N=C(C=2C=CC(=CC=2)C(C)(C)C)C=C1C(=O)NCC1=CC=C(OC(C)(C)C(O)=O)C(C)=C1 HZIOXHZMCMSLJZ-UHFFFAOYSA-N 0.000 claims description 2
- OPCCRUAQNXTYGB-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-2-methylpyrazole-3-carbonyl]amino]methyl]-2,6-dimethylphenoxy]-2-methylpropanoic acid Chemical compound CC1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=CC(=CC=2)C(C)(C)C)C)=C1 OPCCRUAQNXTYGB-UHFFFAOYSA-N 0.000 claims description 2
- MAOVVAJEAXSPFU-UHFFFAOYSA-N 2-[4-[[[5-(4-tert-butylphenyl)-2-methylpyrazole-3-carbonyl]amino]methyl]-2-prop-2-enylphenoxy]-2-methylpropanoic acid Chemical compound CN1N=C(C=2C=CC(=CC=2)C(C)(C)C)C=C1C(=O)NCC1=CC=C(OC(C)(C)C(O)=O)C(CC=C)=C1 MAOVVAJEAXSPFU-UHFFFAOYSA-N 0.000 claims description 2
- DHHNCATZTSKAKM-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[1-methyl-5-(4-phenylmethoxyphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(OCC=4C=CC=CC=4)=CC=3)=C2)=C1 DHHNCATZTSKAKM-UHFFFAOYSA-N 0.000 claims description 2
- SMURNEUIYATOSV-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[1-methyl-5-(4-phenylphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C2=NN(C)C(C=3C=CC(=CC=3)C=3C=CC=CC=3)=C2)=C1 SMURNEUIYATOSV-UHFFFAOYSA-N 0.000 claims description 2
- UFGQMVJKSOQAMR-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[2-methyl-5-(4-phenylmethoxyphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=CC(OCC=3C=CC=CC=3)=CC=2)C)=C1 UFGQMVJKSOQAMR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 206010019280 Heart failures Diseases 0.000 claims 2
- 208000022531 anorexia Diseases 0.000 claims 2
- 206010061428 decreased appetite Diseases 0.000 claims 2
- XGRRRLKUALPLQN-UHFFFAOYSA-N 2-methyl-2-[2-methyl-4-[[[2-methyl-5-(4-prop-2-enoxyphenyl)pyrazole-3-carbonyl]amino]methyl]phenoxy]propanoic acid Chemical compound C1=C(OC(C)(C)C(O)=O)C(C)=CC(CNC(=O)C=2N(N=C(C=2)C=2C=CC(OCC=C)=CC=2)C)=C1 XGRRRLKUALPLQN-UHFFFAOYSA-N 0.000 claims 1
- 208000032841 Bulimia Diseases 0.000 claims 1
- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 abstract 2
- 239000000543 intermediate Substances 0.000 description 451
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 426
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- 239000000243 solution Substances 0.000 description 275
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 219
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 189
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 170
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 166
- 235000019439 ethyl acetate Nutrition 0.000 description 145
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 117
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 114
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
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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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- 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
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
-
- 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
- C07D401/10—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 aromatic rings
-
- 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
- C07D405/10—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 aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Child & Adolescent Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0326747 | 2003-11-17 | ||
| GB0326747A GB0326747D0 (en) | 2003-11-17 | 2003-11-17 | Chemical compounds |
| GB0329462A GB0329462D0 (en) | 2003-12-19 | 2003-12-19 | Chemical compounds |
| GB0329462 | 2003-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2311179T3 true ES2311179T3 (es) | 2009-02-01 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04818779T Expired - Lifetime ES2311179T3 (es) | 2003-11-17 | 2004-11-15 | Pirazoles sustituidos como agonistas de ppar. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20080021030A1 (enExample) |
| EP (1) | EP1685113B1 (enExample) |
| JP (1) | JP2007511485A (enExample) |
| AR (1) | AR046625A1 (enExample) |
| AT (1) | ATE402926T1 (enExample) |
| DE (1) | DE602004015498D1 (enExample) |
| ES (1) | ES2311179T3 (enExample) |
| TW (1) | TW200526588A (enExample) |
| WO (1) | WO2005049578A1 (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JPWO2006004027A1 (ja) * | 2004-07-01 | 2008-04-24 | 第一製薬株式会社 | ピラゾール誘導体 |
| AU2006217682A1 (en) * | 2005-02-28 | 2006-08-31 | Nippon Chemiphar Co., Ltd. | Activator for peroxisome proliferator activating receptor delta |
| NZ564916A (en) * | 2005-06-27 | 2011-03-31 | Exelixis Inc | Imidazole based LXR modulators |
| AU2007239283B2 (en) | 2006-04-18 | 2013-02-07 | Nippon Chemiphar Co., Ltd. | Activating agent for peroxisome proliferator activated receptor delta |
| KR20090094125A (ko) | 2006-12-08 | 2009-09-03 | 엑셀리시스, 인코포레이티드 | Ｌｘｒ 및 ｆｘｒ 조절자 |
| JP2010523623A (ja) * | 2007-04-11 | 2010-07-15 | グラクソ グループ リミテッド | Ｐ２ｘ７調節因子としてのピラゾール誘導体 |
| TWI440633B (zh) | 2008-04-15 | 2014-06-11 | Nippon Chemiphar Co | Activator of Activated Receptors for Peroxisome Producers |
| JP5621148B2 (ja) * | 2008-11-21 | 2014-11-05 | ラクオリア創薬株式会社 | ５−ｈｔ２ｂ受容体拮抗活性を有する新規ピラゾール−３−カルボキサミド誘導体 |
| TW201109335A (en) | 2009-08-04 | 2011-03-16 | Takeda Pharmaceutical | Heterocyclic compounds |
| MX2012006723A (es) * | 2009-12-15 | 2012-06-28 | Bayer Cropscience Ag | Procedimiento para la preparacion de derivados de acido 1-alquil-/1-aril-5-pirazolcarboxilico. |
| TWI508968B (zh) | 2010-02-08 | 2015-11-21 | Biota Scient Management | 用於治療呼吸道融合性病毒感染的化合物 |
| RU2017144535A (ru) | 2010-03-30 | 2019-02-18 | Версеон Корпорейшн | Мультизамещенные ароматические соединения в качестве ингибиторов тромбина |
| CN101870676B (zh) * | 2010-06-24 | 2011-09-07 | 山东大学 | 1-(2-肟基-2-苯基乙基)-3-苯基-1h-吡唑-5-甲酸乙酯衍生物及其制备与应用 |
| PL2968297T3 (pl) | 2013-03-15 | 2019-04-30 | Verseon Corp | Wielopodstawione związki aromatyczne jako inhibitory protezy serynowej |
| BR112015023214A8 (pt) | 2013-03-15 | 2019-12-24 | Verseon Corp | composto, composição farmacêutica, e, uso de um composto ou composição farmacêutica |
| TWI636047B (zh) | 2013-08-14 | 2018-09-21 | 英商卡爾維斯塔製藥有限公司 | 雜環衍生物 |
| EP3194369A4 (en) | 2014-09-17 | 2018-02-28 | Verseon Corporation | Pyrazolyl-substituted pyridone compounds as serine protease inhibitors |
| GB201421083D0 (en) * | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | Enzyme inhibitors |
| GB201421085D0 (en) | 2014-11-27 | 2015-01-14 | Kalvista Pharmaceuticals Ltd | New enzyme inhibitors |
| CA2977993A1 (en) | 2015-02-27 | 2016-09-01 | Verseon Corporation | Substituted pyrazole compounds as serine protease inhibitors |
| SG11201809922YA (en) | 2016-05-31 | 2018-12-28 | Kalvista Pharmaceuticals Ltd | Pyrazole derivatives as plasma kallikrein inhibitors |
| GB201609603D0 (en) | 2016-06-01 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of N-[(6-cyano-2-fluoro-3-methoxyphenyl)Methyl]-3-(methoxymethyl)-1-({4-[(2-ox opyridin-1-YL)Methyl]phenyl}methyl)pyrazole-4-carboxamide |
| GB201609607D0 (en) | 2016-06-01 | 2016-07-13 | Kalvista Pharmaceuticals Ltd | Polymorphs of N-(3-Fluoro-4-methoxypyridin-2-yl)methyl)-3-(methoxymethyl)-1-({4-((2-oxopy ridin-1-yl)methyl)phenyl}methyl)pyrazole-4-carboxamide and salts |
| US10961273B2 (en) | 2016-08-16 | 2021-03-30 | Stealth Biotherapeutics Corp. | N-carboxyanhydride-based-scale synthesis of elamipretide |
| WO2018224455A1 (en) | 2017-06-07 | 2018-12-13 | Basf Se | Substituted cyclopropyl derivatives |
| RS63069B1 (sr) | 2017-11-29 | 2022-04-29 | Kalvista Pharmaceuticals Ltd | Dozni oblici koji sadrže inhibitor kalikreina plazme |
| GB201719881D0 (en) | 2017-11-29 | 2018-01-10 | Kalvista Pharmaceuticals Ltd | Solid forms of plasma kallikrein inhibitor and salts thereof |
| TWI805699B (zh) | 2018-03-01 | 2023-06-21 | 日商日本煙草產業股份有限公司 | 甲基內醯胺環化合物及其用途 |
| CN111902408B (zh) | 2018-04-04 | 2023-11-14 | 日本烟草产业株式会社 | 杂芳基取代的吡唑化合物及其药物用途 |
| JP2021528405A (ja) * | 2018-06-18 | 2021-10-21 | ヤンセン ファーマシューティカ エヌ．ベー． | ＲＯＲγｔのモジュレータとしてのアミド置換チアゾール |
| CN114206852A (zh) | 2019-08-09 | 2022-03-18 | 卡尔维斯塔制药有限公司 | 血浆激肽释放酶抑制剂 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3621775A1 (de) * | 1986-03-13 | 1988-01-07 | Thomae Gmbh Dr K | Neue substituierte thiazole und oxazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| GB9604242D0 (en) * | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
| BR9813019A (pt) * | 1997-10-02 | 2000-09-05 | Sankyo Co | Derivados do ácido amidocarboxìlico, agentes para diminuir a glicose do sangue, redutor de lipìdio, para melhorar a resistência à insulina, anti-inflamatório, para imuno regulagem, para inibir a aldose reductase, para inibir a 5-lipoxigenase, para a geração de supressor de peróxido de lipìdio, para ativar a ppar, para minorar a osteoporose, e, composições para a terapia ou prevenção da diabete melito, da hiperlipemia, da obesidade, da tolerância à glicose prejudicada, da resistência à insulina que não a igt, do fìgado gorduroso, de complicações diabéticas, da arterioesclerose, da diabete melito gestacional, da sìndrome do ovário policìstico, da artroesteìte, da artrite reumática, de doenças alérgicas, da asma, do câncer, de doenças auto imunes, da pancreatite, e de cataratas |
| EP1457490A1 (en) * | 1999-11-10 | 2004-09-15 | Takeda Chemical Industries, Ltd. | 5-membered N-heterocyclic compounds with hypoglycemic and hypolipidemic activity |
| PE20011010A1 (es) * | 1999-12-02 | 2001-10-18 | Glaxo Group Ltd | Oxazoles y tiazoles sustituidos como agonista del receptor activado por el proliferador de peroxisomas humano |
| JP3372923B2 (ja) * | 2000-02-25 | 2003-02-04 | エヌイーシーマイクロシステム株式会社 | 半導体集積回路 |
| AU2003224632A1 (en) * | 2002-03-01 | 2003-09-16 | Smithkline Beecham Corporation | Hppars activators |
-
2004
- 2004-11-12 TW TW093134800A patent/TW200526588A/zh unknown
- 2004-11-15 US US10/595,868 patent/US20080021030A1/en not_active Abandoned
- 2004-11-15 WO PCT/EP2004/012965 patent/WO2005049578A1/en not_active Ceased
- 2004-11-15 AT AT04818779T patent/ATE402926T1/de not_active IP Right Cessation
- 2004-11-15 JP JP2006538823A patent/JP2007511485A/ja active Pending
- 2004-11-15 AR ARP040104209A patent/AR046625A1/es unknown
- 2004-11-15 DE DE602004015498T patent/DE602004015498D1/de not_active Expired - Fee Related
- 2004-11-15 ES ES04818779T patent/ES2311179T3/es not_active Expired - Lifetime
- 2004-11-15 EP EP04818779A patent/EP1685113B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US20080021030A1 (en) | 2008-01-24 |
| AR046625A1 (es) | 2005-12-14 |
| WO2005049578A1 (en) | 2005-06-02 |
| DE602004015498D1 (de) | 2008-09-11 |
| TW200526588A (en) | 2005-08-16 |
| EP1685113B1 (en) | 2008-07-30 |
| JP2007511485A (ja) | 2007-05-10 |
| ATE402926T1 (de) | 2008-08-15 |
| EP1685113A1 (en) | 2006-08-02 |
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