CA2760588C - Fluorinated aminotriazole derivatives - Google Patents
Fluorinated aminotriazole derivatives Download PDFInfo
- Publication number
- CA2760588C CA2760588C CA2760588A CA2760588A CA2760588C CA 2760588 C CA2760588 C CA 2760588C CA 2760588 A CA2760588 A CA 2760588A CA 2760588 A CA2760588 A CA 2760588A CA 2760588 C CA2760588 C CA 2760588C
- Authority
- CA
- Canada
- Prior art keywords
- oxazole
- ethyl
- triazol
- difluoro
- carboxylic acid
- 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 - Fee Related
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- JSIAIROWMJGMQZ-UHFFFAOYSA-N 2h-triazol-4-amine Chemical class NC1=CNN=N1 JSIAIROWMJGMQZ-UHFFFAOYSA-N 0.000 title abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 184
- 150000003839 salts Chemical class 0.000 claims description 109
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 51
- -1 chloro, methyl Chemical group 0.000 claims description 39
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
- 201000010099 disease Diseases 0.000 claims description 32
- 238000011282 treatment Methods 0.000 claims description 30
- 230000001404 mediated effect Effects 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 208000027866 inflammatory disease Diseases 0.000 claims description 23
- 208000035475 disorder Diseases 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 230000002265 prevention Effects 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 16
- 108091000054 Prion Proteins 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 14
- 208000023504 respiratory system disease Diseases 0.000 claims description 14
- 206010027654 Allergic conditions Diseases 0.000 claims description 12
- 125000001153 fluoro group Chemical group F* 0.000 claims description 12
- 230000000414 obstructive effect Effects 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 208000002193 Pain Diseases 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 208000012902 Nervous system disease Diseases 0.000 claims description 8
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims description 8
- 208000025966 Neurological disease Diseases 0.000 claims description 8
- 102000029797 Prion Human genes 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 230000028993 immune response Effects 0.000 claims description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 8
- 230000003959 neuroinflammation Effects 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 7
- 206010038997 Retroviral infections Diseases 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000001543 furan-2,5-diyl group Chemical group O1C(=CC=C1*)* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- UWBDPFNZFSRIFR-UHFFFAOYSA-N 2-cyclopropyl-n-[2-[[4-(1,1-difluoroethyl)-1,3-thiazol-2-yl]methyl]triazol-4-yl]-5-phenyl-1,3-oxazole-4-carboxamide Chemical compound CC(F)(F)C1=CSC(CN2N=C(NC(=O)C3=C(OC(=N3)C3CC3)C=3C=CC=CC=3)C=N2)=N1 UWBDPFNZFSRIFR-UHFFFAOYSA-N 0.000 claims 1
- MAKKUOPYKAKDGW-UHFFFAOYSA-N 5-(3-chlorophenyl)-n-[2-[[4-(1,1-difluoroethyl)-1,3-thiazol-2-yl]methyl]triazol-4-yl]-1,3-oxazole-4-carboxamide Chemical compound CC(F)(F)C1=CSC(CN2N=C(NC(=O)C3=C(OC=N3)C=3C=C(Cl)C=CC=3)C=N2)=N1 MAKKUOPYKAKDGW-UHFFFAOYSA-N 0.000 claims 1
- MIQSCPMLFPEIRE-UHFFFAOYSA-N 5-(3-chlorophenyl)-n-[2-[[4-(1,1-difluoroethyl)-1,3-thiazol-2-yl]methyl]triazol-4-yl]-2-methyl-1,3-oxazole-4-carboxamide Chemical compound C=1C=CC(Cl)=CC=1C=1OC(C)=NC=1C(=O)NC(=N1)C=NN1CC1=NC(C(C)(F)F)=CS1 MIQSCPMLFPEIRE-UHFFFAOYSA-N 0.000 claims 1
- VBSWJHUAYAVBJN-UHFFFAOYSA-N 5-(3-chlorophenyl)-n-[2-[[5-(1,1-difluoroethyl)furan-2-yl]methyl]triazol-4-yl]-1,3-oxazole-4-carboxamide Chemical compound O1C(C(F)(F)C)=CC=C1CN1N=C(NC(=O)C2=C(OC=N2)C=2C=C(Cl)C=CC=2)C=N1 VBSWJHUAYAVBJN-UHFFFAOYSA-N 0.000 claims 1
- ICNNISYXABMDEP-UHFFFAOYSA-N 5-(3-chlorophenyl)-n-[2-[[5-(1,1-difluoroethyl)furan-2-yl]methyl]triazol-4-yl]-2-methyl-1,3-oxazole-4-carboxamide Chemical compound C=1C=CC(Cl)=CC=1C=1OC(C)=NC=1C(=O)NC(=N1)C=NN1CC1=CC=C(C(C)(F)F)O1 ICNNISYXABMDEP-UHFFFAOYSA-N 0.000 claims 1
- IEBFJPSUARKTDM-UHFFFAOYSA-N n-[2-[[2-(1,1-difluoroethyl)-1,3-oxazol-4-yl]methyl]triazol-4-yl]-2-methyl-5-(3-methylphenyl)-1,3-oxazole-4-carboxamide Chemical compound C=1C=CC(C)=CC=1C=1OC(C)=NC=1C(=O)NC(=N1)C=NN1CC1=COC(C(C)(F)F)=N1 IEBFJPSUARKTDM-UHFFFAOYSA-N 0.000 claims 1
- PBTWPEDVIMHJEO-UHFFFAOYSA-N n-[2-[[4-(1,1-difluoroethyl)-1,3-oxazol-2-yl]methyl]triazol-4-yl]-2-methyl-5-(3-methylphenyl)-1,3-oxazole-4-carboxamide Chemical compound C=1C=CC(C)=CC=1C=1OC(C)=NC=1C(=O)NC(=N1)C=NN1CC1=NC(C(C)(F)F)=CO1 PBTWPEDVIMHJEO-UHFFFAOYSA-N 0.000 claims 1
- SNXPZBANHWAGLP-UHFFFAOYSA-N n-[2-[[4-(1,1-difluoroethyl)-1,3-oxazol-2-yl]methyl]triazol-4-yl]-2-methyl-5-phenyl-1,3-oxazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1OC(C)=NC=1C(=O)NC(=N1)C=NN1CC1=NC(C(C)(F)F)=CO1 SNXPZBANHWAGLP-UHFFFAOYSA-N 0.000 claims 1
- IZEPAJCGKCGWDG-UHFFFAOYSA-N n-[2-[[4-(1,1-difluoroethyl)-1,3-oxazol-2-yl]methyl]triazol-4-yl]-5-[3-(dimethylamino)-4-fluorophenyl]-1,3-oxazole-4-carboxamide Chemical compound C1=C(F)C(N(C)C)=CC(C2=C(N=CO2)C(=O)NC2=NN(CC=3OC=C(N=3)C(C)(F)F)N=C2)=C1 IZEPAJCGKCGWDG-UHFFFAOYSA-N 0.000 claims 1
- NWILTWALAFDYML-UHFFFAOYSA-N n-[2-[[4-(1,1-difluoroethyl)-1,3-oxazol-2-yl]methyl]triazol-4-yl]-5-[3-(dimethylamino)-4-fluorophenyl]-2-methyl-1,3-oxazole-4-carboxamide Chemical compound C1=C(F)C(N(C)C)=CC(C2=C(N=C(C)O2)C(=O)NC2=NN(CC=3OC=C(N=3)C(C)(F)F)N=C2)=C1 NWILTWALAFDYML-UHFFFAOYSA-N 0.000 claims 1
- QPKKEHQQYRJQLD-UHFFFAOYSA-N n-[2-[[4-(1,1-difluoroethyl)-1,3-oxazol-2-yl]methyl]triazol-4-yl]-5-[3-(dimethylamino)phenyl]-1,3-oxazole-4-carboxamide Chemical compound CN(C)C1=CC=CC(C2=C(N=CO2)C(=O)NC2=NN(CC=3OC=C(N=3)C(C)(F)F)N=C2)=C1 QPKKEHQQYRJQLD-UHFFFAOYSA-N 0.000 claims 1
- VFPUUYHTNXSBGW-UHFFFAOYSA-N n-[2-[[4-(1,1-difluoroethyl)-1,3-thiazol-2-yl]methyl]triazol-4-yl]-2-ethyl-5-phenyl-1,3-oxazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1OC(CC)=NC=1C(=O)NC(=N1)C=NN1CC1=NC(C(C)(F)F)=CS1 VFPUUYHTNXSBGW-UHFFFAOYSA-N 0.000 claims 1
- GVCXEFKLMNKTGI-UHFFFAOYSA-N n-[2-[[4-(1,1-difluoroethyl)-1,3-thiazol-2-yl]methyl]triazol-4-yl]-2-methyl-5-(3-methylphenyl)-1,3-oxazole-4-carboxamide Chemical compound C=1C=CC(C)=CC=1C=1OC(C)=NC=1C(=O)NC(=N1)C=NN1CC1=NC(C(C)(F)F)=CS1 GVCXEFKLMNKTGI-UHFFFAOYSA-N 0.000 claims 1
- VTNMLIDXHPDHSX-UHFFFAOYSA-N n-[2-[[4-(1,1-difluoroethyl)-1,3-thiazol-2-yl]methyl]triazol-4-yl]-2-methyl-5-[3-(trifluoromethoxy)phenyl]-1,3-oxazole-4-carboxamide Chemical compound C=1C=CC(OC(F)(F)F)=CC=1C=1OC(C)=NC=1C(=O)NC(=N1)C=NN1CC1=NC(C(C)(F)F)=CS1 VTNMLIDXHPDHSX-UHFFFAOYSA-N 0.000 claims 1
- MMXOWBIRKHCZMW-UHFFFAOYSA-N n-[2-[[4-(1,1-difluoroethyl)-1,3-thiazol-2-yl]methyl]triazol-4-yl]-2-methyl-5-[3-(trifluoromethyl)phenyl]-1,3-oxazole-4-carboxamide Chemical compound C=1C=CC(C(F)(F)F)=CC=1C=1OC(C)=NC=1C(=O)NC(=N1)C=NN1CC1=NC(C(C)(F)F)=CS1 MMXOWBIRKHCZMW-UHFFFAOYSA-N 0.000 claims 1
- SGZGNKVJYPCPGJ-UHFFFAOYSA-N n-[2-[[4-(1,1-difluoroethyl)-1,3-thiazol-2-yl]methyl]triazol-4-yl]-2-methyl-5-phenyl-1,3-oxazole-4-carboxamide Chemical compound C=1C=CC=CC=1C=1OC(C)=NC=1C(=O)NC(=N1)C=NN1CC1=NC(C(C)(F)F)=CS1 SGZGNKVJYPCPGJ-UHFFFAOYSA-N 0.000 claims 1
- GMRYZVAVQYWKPU-UHFFFAOYSA-N n-[2-[[4-(1,1-difluoroethyl)-1,3-thiazol-2-yl]methyl]triazol-4-yl]-5-(3,5-difluorophenyl)-2-methyl-1,3-oxazole-4-carboxamide Chemical compound C=1C(F)=CC(F)=CC=1C=1OC(C)=NC=1C(=O)NC(=N1)C=NN1CC1=NC(C(C)(F)F)=CS1 GMRYZVAVQYWKPU-UHFFFAOYSA-N 0.000 claims 1
- MYGJIYRSAWJOBG-UHFFFAOYSA-N n-[2-[[4-(1,1-difluoroethyl)-1,3-thiazol-2-yl]methyl]triazol-4-yl]-5-(3-fluoro-5-methylphenyl)-2-methyl-1,3-oxazole-4-carboxamide Chemical compound C=1C(C)=CC(F)=CC=1C=1OC(C)=NC=1C(=O)NC(=N1)C=NN1CC1=NC(C(C)(F)F)=CS1 MYGJIYRSAWJOBG-UHFFFAOYSA-N 0.000 claims 1
- QMFWNPOSOYGXOZ-UHFFFAOYSA-N n-[2-[[4-(1,1-difluoroethyl)-1,3-thiazol-2-yl]methyl]triazol-4-yl]-5-(3-fluorophenyl)-1,3-oxazole-4-carboxamide Chemical compound CC(F)(F)C1=CSC(CN2N=C(NC(=O)C3=C(OC=N3)C=3C=C(F)C=CC=3)C=N2)=N1 QMFWNPOSOYGXOZ-UHFFFAOYSA-N 0.000 claims 1
- GZVDOSCJJAVEPH-UHFFFAOYSA-N n-[2-[[4-(1,1-difluoroethyl)-1,3-thiazol-2-yl]methyl]triazol-4-yl]-5-(3-methoxyphenyl)-1,3-oxazole-4-carboxamide Chemical compound COC1=CC=CC(C2=C(N=CO2)C(=O)NC2=NN(CC=3SC=C(N=3)C(C)(F)F)N=C2)=C1 GZVDOSCJJAVEPH-UHFFFAOYSA-N 0.000 claims 1
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
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- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/14—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4
- A61P5/16—Drugs for disorders of the endocrine system of the thyroid hormones, e.g. T3, T4 for decreasing, blocking or antagonising the activity of the thyroid hormones
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- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
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- 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
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- 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
- C07D413/12—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 chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- Health & Medical Sciences (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| IB2009052445 | 2009-06-09 | ||
| IBPCT/IB2009/052445 | 2009-06-09 | ||
| PCT/IB2010/052509 WO2010143116A1 (en) | 2009-06-09 | 2010-06-07 | Fluorinated aminotriazole derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2760588A1 CA2760588A1 (en) | 2010-12-16 |
| CA2760588C true CA2760588C (en) | 2017-08-08 |
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| Application Number | Title | Priority Date | Filing Date |
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| EP (1) | EP2440555B1 (enExample) |
| JP (2) | JP5095035B2 (enExample) |
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| AU (1) | AU2010258334B2 (enExample) |
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| IL (1) | IL216792A (enExample) |
| MA (1) | MA33420B1 (enExample) |
| MX (1) | MX342440B (enExample) |
| MY (1) | MY161243A (enExample) |
| NZ (1) | NZ597453A (enExample) |
| PL (1) | PL2440555T3 (enExample) |
| RU (1) | RU2544862C2 (enExample) |
| SG (1) | SG175363A1 (enExample) |
| TW (1) | TWI404717B (enExample) |
| WO (1) | WO2010143116A1 (enExample) |
| ZA (1) | ZA201200127B (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
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| AR069650A1 (es) | 2007-12-14 | 2010-02-10 | Actelion Pharmaceuticals Ltd | Derivados de aminopirazol como agonistas no peptidicos del receptor alx humano |
| SI2225231T1 (sl) | 2007-12-18 | 2011-12-30 | Actelion Pharmaceuticals Ltd | Derivati aminotriazola kot alx agonisti |
| JP5510945B2 (ja) | 2009-05-18 | 2014-06-04 | アクテリオン ファーマシューティカルズ リミテッド | Ａｌｘ受容体及び／又はｆｐｒｌ２アゴニストとしての架橋スピロ［２．４］ヘプタン誘導体 |
| WO2010143158A1 (en) | 2009-06-12 | 2010-12-16 | Actelion Pharmaceuticals Ltd | Oxazole and thiazole derivatives as alx receptor agonists |
| ES2553635T3 (es) | 2010-11-17 | 2015-12-10 | Actelion Pharmaceuticals Ltd. | Derivados de éster spiro[2.4]heptano puenteados |
| BR112013014035A2 (pt) * | 2010-12-07 | 2016-09-13 | Actelion Pharmaceuticals Ltd | derivados de aminotriazol hidroxilado como agonistas dos receptores de alx |
| PL2649068T3 (pl) * | 2010-12-07 | 2015-03-31 | Idorsia Pharmaceuticals Ltd | Pochodne eteru oksazolilowo-metylowego jako agoniści receptora ALX |
| ES2596521T3 (es) | 2012-05-16 | 2017-01-10 | Actelion Pharmaceuticals Ltd. | Derivados de espiro[2.4]heptano sustituidos con puente 1-(p-tolil)ciclopropilo como agonistas de receptor de ALX |
| MA37618B1 (fr) | 2012-05-16 | 2017-08-31 | Actelion Pharmaceuticals Ltd | Dérivés pontés fluorés de spiro[2.4]heptane en tant qu'agonistes de récepteur alx |
| PL2855453T3 (pl) | 2012-06-04 | 2017-05-31 | Actelion Pharmaceuticals Ltd. | Pochodne benzimidazoloproliny |
| CN104703980B (zh) | 2012-10-10 | 2017-09-22 | 埃科特莱茵药品有限公司 | 属于[邻双(杂)芳基]‑[2‑(间双(杂)芳基)吡咯烷‑1‑基]甲酮衍生物的食欲素受体拮抗剂 |
| WO2014141065A1 (en) | 2013-03-12 | 2014-09-18 | Actelion Pharmaceuticals Ltd | Azetidine amide derivatives as orexin receptor antagonists |
| JP6366195B2 (ja) | 2013-04-22 | 2018-08-01 | 国立大学法人 東京大学 | 炎症性疾患の予防又は治療剤 |
| AR096686A1 (es) | 2013-06-25 | 2016-01-27 | Actelion Pharmaceuticals Ltd | Derivados de espiro[2.4]heptano puenteados sustituidos con difluoroetil-oxazol como agonistas del receptor de alx |
| CN105377824B (zh) | 2013-07-18 | 2017-08-04 | 埃科特莱茵药品有限公司 | 作为alx受体激动剂的经哌嗪取代桥联螺[2,4]庚烷衍生物 |
| AR097279A1 (es) | 2013-08-09 | 2016-03-02 | Actelion Pharmaceuticals Ltd | Derivados de benzimidazolil-metil urea como agonistas del receptor de alx |
| EP3077391B1 (en) | 2013-12-04 | 2018-08-15 | Idorsia Pharmaceuticals Ltd | Use of benzimidazole-proline derivatives |
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| JPS62234018A (ja) | 1986-04-02 | 1987-10-14 | Rooto Seiyaku Kk | 糖尿病併発症治療剤 |
| FR2763337B1 (fr) * | 1997-05-13 | 1999-08-20 | Sanofi Sa | Nouveaux derives du triazole, un procede pour leur preparation et compositions pharmaceutiques les contenant |
| KR20030030029A (ko) | 2000-09-22 | 2003-04-16 | 니혼노야쿠가부시키가이샤 | Ｎ-(4-피라졸릴)아미드 유도체 및 농원예용 약제 그리고그 사용방법 |
| US20050164305A1 (en) | 2002-04-03 | 2005-07-28 | Bayer Healthcare Ag | Diagnostics and therapeutics for diseases associated with n-formyl peptide receptor like 1 (fprl1) |
| TWI335913B (en) * | 2002-11-15 | 2011-01-11 | Vertex Pharma | Diaminotriazoles useful as inhibitors of protein kinases |
| CA2544983A1 (en) | 2003-11-07 | 2005-05-26 | Acadia Pharmaceuticals Inc. | Use of the lipoxin receptor, fprl1, as a tool for identifying compounds effective in the treatment of pain and inflammation |
| AU2005247473A1 (en) * | 2004-05-25 | 2005-12-08 | Metabolex, Inc. | Substituted triazoles as modulators of PPAR and methods of their preparation |
| DE602005025655D1 (de) * | 2004-09-17 | 2011-02-10 | Vertex Pharma | Als proteinkinaseinhibitoren geeignete diaminotriazolverbindungen |
| US20060293288A1 (en) | 2005-01-07 | 2006-12-28 | Serhan Charles N | Use of resolvins to treat gastrointestinal diseases |
| WO2007055941A2 (en) * | 2005-11-03 | 2007-05-18 | Merck & Co., Inc. | Histone deacetylase inhibitors with aryl-pyrazolyl motifs |
| US7939671B2 (en) | 2007-08-21 | 2011-05-10 | Senomyx, Inc. | Compounds that inhibit (block) bitter taste in composition and use thereof |
| AR069650A1 (es) | 2007-12-14 | 2010-02-10 | Actelion Pharmaceuticals Ltd | Derivados de aminopirazol como agonistas no peptidicos del receptor alx humano |
| SI2225231T1 (sl) * | 2007-12-18 | 2011-12-30 | Actelion Pharmaceuticals Ltd | Derivati aminotriazola kot alx agonisti |
| JP5510945B2 (ja) | 2009-05-18 | 2014-06-04 | アクテリオン ファーマシューティカルズ リミテッド | Ａｌｘ受容体及び／又はｆｐｒｌ２アゴニストとしての架橋スピロ［２．４］ヘプタン誘導体 |
| WO2010143158A1 (en) | 2009-06-12 | 2010-12-16 | Actelion Pharmaceuticals Ltd | Oxazole and thiazole derivatives as alx receptor agonists |
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2010
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- 2010-06-07 CN CN201080018293.6A patent/CN102414207B/zh not_active Expired - Fee Related
- 2010-06-07 KR KR1020127000486A patent/KR101444559B1/ko not_active Expired - Fee Related
- 2010-06-07 MA MA34521A patent/MA33420B1/fr unknown
- 2010-06-07 SG SG2011078706A patent/SG175363A1/en unknown
- 2010-06-07 RU RU2011153772/04A patent/RU2544862C2/ru not_active IP Right Cessation
- 2010-06-07 PL PL10725500.2T patent/PL2440555T3/pl unknown
- 2010-06-07 WO PCT/IB2010/052509 patent/WO2010143116A1/en not_active Ceased
- 2010-06-07 CA CA2760588A patent/CA2760588C/en not_active Expired - Fee Related
- 2010-06-07 JP JP2012514570A patent/JP5095035B2/ja not_active Expired - Fee Related
- 2010-06-07 ES ES10725500.2T patent/ES2587139T3/es active Active
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- 2010-06-07 AU AU2010258334A patent/AU2010258334B2/en not_active Ceased
- 2010-06-07 US US13/376,966 patent/US8580831B2/en not_active Expired - Fee Related
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- 2010-06-08 TW TW099118594A patent/TWI404717B/zh not_active IP Right Cessation
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2011
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2012
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