ES2612205T3 - Derivados de pirazol y su uso como antagonistas de LPAR5 - Google Patents
Derivados de pirazol y su uso como antagonistas de LPAR5 Download PDFInfo
- Publication number
- ES2612205T3 ES2612205T3 ES13723151.0T ES13723151T ES2612205T3 ES 2612205 T3 ES2612205 T3 ES 2612205T3 ES 13723151 T ES13723151 T ES 13723151T ES 2612205 T3 ES2612205 T3 ES 2612205T3
- Authority
- ES
- Spain
- Prior art keywords
- methyl
- alkyl
- series consisting
- pyrazol
- phenyl
- 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.)
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- 101001038037 Homo sapiens Lysophosphatidic acid receptor 5 Proteins 0.000 title description 8
- 150000003217 pyrazoles Chemical class 0.000 title description 4
- 102100040404 Lysophosphatidic acid receptor 5 Human genes 0.000 title description 2
- 239000005557 antagonist Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 55
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract description 38
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 37
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 28
- 239000001257 hydrogen Substances 0.000 abstract description 28
- 150000003839 salts Chemical class 0.000 abstract description 24
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 17
- 150000002367 halogens Chemical class 0.000 abstract description 17
- 229910052736 halogen Inorganic materials 0.000 abstract description 16
- 239000002253 acid Substances 0.000 abstract description 15
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 13
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 11
- 150000002431 hydrogen Chemical class 0.000 abstract description 10
- 125000001424 substituent group Chemical group 0.000 abstract description 10
- 239000005711 Benzoic acid Substances 0.000 abstract description 9
- 125000000217 alkyl group Chemical group 0.000 abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 abstract description 7
- 239000011737 fluorine Substances 0.000 abstract description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract description 6
- CYAYCOCJAVHQSD-UHFFFAOYSA-N 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxylic acid Chemical compound CC=1C(C(O)=O)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 CYAYCOCJAVHQSD-UHFFFAOYSA-N 0.000 abstract description 6
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 abstract description 6
- 235000010233 benzoic acid Nutrition 0.000 abstract description 5
- 125000001624 naphthyl group Chemical group 0.000 abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 abstract description 4
- 125000005842 heteroatom Chemical group 0.000 abstract description 3
- 229910052799 carbon Inorganic materials 0.000 abstract description 2
- 125000001153 fluoro group Chemical group F* 0.000 abstract description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 3
- CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 abstract 1
- MPYWLRINLUDPAC-UHFFFAOYSA-N 2-[[1-(2,4-dichlorophenyl)-4-methyl-5-[4-(trifluoromethoxy)phenyl]pyrazol-3-yl]methoxy]-2-methylpropanamide Chemical compound ClC1=C(C=CC(=C1)Cl)N1N=C(C(=C1C1=CC=C(C=C1)OC(F)(F)F)C)COC(C(=O)N)(C)C MPYWLRINLUDPAC-UHFFFAOYSA-N 0.000 abstract 1
- CVIVKICGOJSLOU-UHFFFAOYSA-N 2-[[1-(2,4-dichlorophenyl)-4-methyl-5-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]methoxy]-2-methylpropanamide Chemical compound ClC1=C(C=CC(=C1)Cl)N1N=C(C(=C1C1=CC=C(C=C1)C(F)(F)F)C)COC(C(=O)N)(C)C CVIVKICGOJSLOU-UHFFFAOYSA-N 0.000 abstract 1
- WEBVPMDXUUILMS-UHFFFAOYSA-N 4-[[2-[[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]methoxy]butanoylamino]methyl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1CNC(=O)C(CC)OCC(C=1C)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 WEBVPMDXUUILMS-UHFFFAOYSA-N 0.000 abstract 1
- SWSUPYGXAKUHMG-UHFFFAOYSA-N 4-[[2-[[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]methoxy]propanoylamino]methyl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1CNC(=O)C(C)OCC(C=1C)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 SWSUPYGXAKUHMG-UHFFFAOYSA-N 0.000 abstract 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 150000001924 cycloalkanes Chemical class 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 239000000651 prodrug Substances 0.000 description 15
- 229940002612 prodrug Drugs 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 238000000034 method Methods 0.000 description 14
- 210000001772 blood platelet Anatomy 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000011282 treatment Methods 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 210000003630 histaminocyte Anatomy 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 9
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 230000004913 activation Effects 0.000 description 7
- 210000004623 platelet-rich plasma Anatomy 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 239000000872 buffer Substances 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- 229910052744 lithium Inorganic materials 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- 230000002776 aggregation Effects 0.000 description 5
- 238000004220 aggregation Methods 0.000 description 5
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 5
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 208000001435 Thromboembolism Diseases 0.000 description 4
- -1 alkali metal salts Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000020411 cell activation Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 4
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 4
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 3
- IZTJZHLFCPFXPR-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-4-methyl-5-[4-(trifluoromethyl)phenyl]pyrazole-3-carboxylic acid Chemical compound CC=1C(C(O)=O)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(C(F)(F)F)C=C1 IZTJZHLFCPFXPR-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
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- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
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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
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
-
- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
-
- 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
-
- 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
- C07D409/12—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 chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12305552 | 2012-05-18 | ||
| EP12305552 | 2012-05-18 | ||
| PCT/EP2013/060171 WO2013171317A1 (en) | 2012-05-18 | 2013-05-16 | Pyrazole derivatives and their use as lpar5 antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2612205T3 true ES2612205T3 (es) | 2017-05-12 |
Family
ID=48446368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13723151.0T Active ES2612205T3 (es) | 2012-05-18 | 2013-05-16 | Derivados de pirazol y su uso como antagonistas de LPAR5 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US9346762B2 (https=) |
| EP (1) | EP2882715B1 (https=) |
| JP (1) | JP6257596B2 (https=) |
| KR (1) | KR20150010973A (https=) |
| CN (1) | CN104302625B (https=) |
| AU (1) | AU2013261718B2 (https=) |
| BR (1) | BR112014028406A2 (https=) |
| CA (1) | CA2871542A1 (https=) |
| CY (1) | CY1118618T1 (https=) |
| DK (1) | DK2882715T3 (https=) |
| ES (1) | ES2612205T3 (https=) |
| HR (1) | HRP20170098T1 (https=) |
| HU (1) | HUE032890T2 (https=) |
| IL (1) | IL235221A (https=) |
| LT (1) | LT2882715T (https=) |
| MX (1) | MX347615B (https=) |
| PL (1) | PL2882715T3 (https=) |
| PT (1) | PT2882715T (https=) |
| RU (1) | RU2645344C2 (https=) |
| SG (1) | SG11201407210SA (https=) |
| SI (1) | SI2882715T1 (https=) |
| WO (1) | WO2013171317A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2850062B1 (en) | 2012-05-18 | 2017-07-19 | Sanofi | Pyridine derivatives and their use in the treatment of conditions associated with pathological thrombus formation |
| BR112017026535B1 (pt) | 2015-06-12 | 2023-12-19 | Vettore, LLC | Composto e composição farmacêutica |
| WO2018111904A1 (en) | 2016-12-12 | 2018-06-21 | Vettore, LLC | Heterocyclic inhibitors of mct4 |
| PL4038052T3 (pl) | 2019-10-02 | 2024-08-26 | Domain Therapeutics | Antagoniści receptora ep4 prostaglandyny e2 (pge2) |
| WO2024092205A1 (en) * | 2022-10-27 | 2024-05-02 | The Trustees Of Indiana University | Inhibition of ship1 as a therapeutic strategy for the treatment of alzheimer's disease |
| CN119930520B (zh) * | 2023-11-03 | 2026-03-06 | 中国药科大学 | N-芳基吡唑类化合物及其药物组合物和应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1230441B (it) | 1989-02-07 | 1991-10-23 | Acraf | Eteri della serie dell'indazolo |
| US7279478B2 (en) | 2002-09-04 | 2007-10-09 | Merck Frosst Canada & Co. | Cathepsin cysteine protease inhibitors |
| EP2118066A1 (en) | 2007-02-09 | 2009-11-18 | Takeda Pharmaceutical Company Limited | Fused ring compounds as partial agonists of ppar-gamma |
| WO2009080227A2 (en) | 2007-12-26 | 2009-07-02 | Sanofi-Aventis | Pyrazole-carboxamide derivatives as p2y12 antagonists |
| JP5509100B2 (ja) | 2008-03-07 | 2014-06-04 | アジェンデ・キミケ・リウニテ・アンジェリニ・フランチェスコ・ア・チ・エレ・ア・エフェ・ソシエタ・ペル・アチオニ | 新規な１−ベンジル−３−ヒドロキシメチルインダゾール誘導体及びそのＭＣＰ−１，ＣＸ３ＣＲ１及びｐ４０の発現に基づく疾病の治療への使用 |
| EA019711B1 (ru) * | 2008-03-07 | 2014-05-30 | Ацьенде Кимике Рьюните Анджелини Франческо A.K.P.A.Ф. С.П.А. | ПРОИЗВОДНЫЕ 1-БЕНЗИЛ-3-ГИДРОКСИМЕТИЛИНДАЗОЛА, СОДЕРЖАЩАЯ ИХ ФАРМАЦЕВТИЧЕСКАЯ КОМПОЗИЦИЯ И ИХ ПРИМЕНЕНИЕ ПРИ ЛЕЧЕНИИ ЗАБОЛЕВАНИЙ, ОБУСЛОВЛЕННЫХ ЭКСПРЕССИЕЙ МСР-1, СХ3CR1 ИЛИ р40 |
| KR20110128942A (ko) * | 2009-03-19 | 2011-11-30 | 사노피 | Ｈｓｐ９０ 억제 인다졸 유도체, 그를 함유하는 조성물 및 그의 용도 |
| GEP20135879B (en) | 2009-08-03 | 2013-07-10 | Aziende Chimiche Riunite Angelini Francesco A C R A F S P A It | Method of 1-benzyl-3-hydroxymethyl-1h-indazole preparation, derivatives thereof, and required magnesium intermediates |
| ES2530345T3 (es) * | 2010-09-02 | 2015-03-02 | Merck Patent Gmbh | Derivados de pirazolopiridinona como antagonistas del receptor del LPA |
| EP2850062B1 (en) | 2012-05-18 | 2017-07-19 | Sanofi | Pyridine derivatives and their use in the treatment of conditions associated with pathological thrombus formation |
-
2013
- 2013-05-16 US US14/401,050 patent/US9346762B2/en not_active Expired - Fee Related
- 2013-05-16 PL PL13723151T patent/PL2882715T3/pl unknown
- 2013-05-16 HU HUE13723151A patent/HUE032890T2/hu unknown
- 2013-05-16 WO PCT/EP2013/060171 patent/WO2013171317A1/en not_active Ceased
- 2013-05-16 DK DK13723151.0T patent/DK2882715T3/en active
- 2013-05-16 CN CN201380025967.9A patent/CN104302625B/zh not_active Expired - Fee Related
- 2013-05-16 CA CA2871542A patent/CA2871542A1/en not_active Abandoned
- 2013-05-16 JP JP2015512072A patent/JP6257596B2/ja not_active Expired - Fee Related
- 2013-05-16 BR BR112014028406A patent/BR112014028406A2/pt not_active Application Discontinuation
- 2013-05-16 HR HRP20170098TT patent/HRP20170098T1/hr unknown
- 2013-05-16 AU AU2013261718A patent/AU2013261718B2/en not_active Ceased
- 2013-05-16 PT PT137231510T patent/PT2882715T/pt unknown
- 2013-05-16 MX MX2014014011A patent/MX347615B/es active IP Right Grant
- 2013-05-16 EP EP13723151.0A patent/EP2882715B1/en not_active Not-in-force
- 2013-05-16 SG SG11201407210SA patent/SG11201407210SA/en unknown
- 2013-05-16 SI SI201330499A patent/SI2882715T1/sl unknown
- 2013-05-16 LT LTEP13723151.0T patent/LT2882715T/lt unknown
- 2013-05-16 KR KR20147033843A patent/KR20150010973A/ko not_active Ceased
- 2013-05-16 ES ES13723151.0T patent/ES2612205T3/es active Active
- 2013-05-16 RU RU2014151360A patent/RU2645344C2/ru not_active IP Right Cessation
-
2014
- 2014-10-20 IL IL235221A patent/IL235221A/en active IP Right Grant
-
2017
- 2017-02-08 CY CY20171100175T patent/CY1118618T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SI2882715T1 (sl) | 2017-03-31 |
| EP2882715A1 (en) | 2015-06-17 |
| SG11201407210SA (en) | 2014-12-30 |
| US9346762B2 (en) | 2016-05-24 |
| JP6257596B2 (ja) | 2018-01-10 |
| DK2882715T3 (en) | 2017-02-13 |
| CA2871542A1 (en) | 2013-11-21 |
| AU2013261718A1 (en) | 2014-12-18 |
| KR20150010973A (ko) | 2015-01-29 |
| RU2014151360A (ru) | 2016-07-10 |
| CN104302625B (zh) | 2017-04-19 |
| US20150141477A1 (en) | 2015-05-21 |
| CN104302625A (zh) | 2015-01-21 |
| PL2882715T3 (pl) | 2017-04-28 |
| CY1118618T1 (el) | 2017-07-12 |
| MX2014014011A (es) | 2015-02-12 |
| HUE032890T2 (hu) | 2017-11-28 |
| IL235221A (en) | 2016-06-30 |
| BR112014028406A2 (pt) | 2017-06-27 |
| WO2013171317A1 (en) | 2013-11-21 |
| JP2015517514A (ja) | 2015-06-22 |
| RU2645344C2 (ru) | 2018-02-21 |
| LT2882715T (lt) | 2017-02-10 |
| PT2882715T (pt) | 2016-12-30 |
| EP2882715B1 (en) | 2016-11-09 |
| HRP20170098T1 (hr) | 2017-03-24 |
| MX347615B (es) | 2017-05-04 |
| AU2013261718B2 (en) | 2017-10-19 |
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