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)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (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 |
|---|---|---|---|---|
| JP2015521183A (ja) | 2012-05-18 | 2015-07-27 | サノフイ | ピリジン誘導体および病理学的血栓形成に関連する状態の治療へのその使用 |
| EP3942934A1 (en) | 2015-06-12 | 2022-01-26 | Vettore, LLC | Mct4 inhibitors for treating disease |
| US10214492B2 (en) | 2016-12-12 | 2019-02-26 | Vettore, LLC | Heterocyclic inhibitors of MCT4 |
| CN114555573B (zh) | 2019-10-02 | 2025-08-15 | 多曼治疗学公司 | 前列腺素e2(pge2)ep4受体拮抗剂 |
| 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 |
| EP1537074B1 (en) | 2002-09-04 | 2019-02-27 | Merck Canada Inc. | Cathepsin cysteine protease inhibitors |
| JP2010517935A (ja) | 2007-02-09 | 2010-05-27 | 武田薬品工業株式会社 | Ｐｐａｒ−ガンマのパーシャルアゴニストとしての縮合環化合物 |
| EP2238127B1 (en) | 2007-12-26 | 2012-08-15 | Sanofi | Pyrazole-carboxamide derivatives as p2y12 antagonists |
| HRP20191953T8 (hr) | 2008-03-07 | 2021-06-25 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | DERIVATI 1-BENZIL-3-HIDROKSIMETILINDAZOLA I NJIHOVA UPORABA U LIJEČENJU BOLESTI KOJE SE BAZIRAJU NA EKSPRESIJI MCP-1, CX3CR1 i P40 |
| WO2009109613A2 (en) * | 2008-03-07 | 2009-09-11 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | Novel 1-benzyl-3-hydroxymethylindazole derivatives and use thereof in the treatment of diseases based on the expression of mcp-1, cx3cr1 and p40 |
| CN102439003A (zh) * | 2009-03-19 | 2012-05-02 | 赛诺菲 | 抑制hsp90的吲唑衍生物、含有所述衍生物的组合物及其用途 |
| EA019060B1 (ru) * | 2009-08-03 | 2013-12-30 | Ацьенде Кимике Рьюните Анджелини Франческо А.К.Р.А.Ф. С.П.А. | Способ получения 1-бензил-3-гидроксиметил-1н-индазола и его производных и необходимые промежуточные соединения с магнием |
| JP6039559B2 (ja) * | 2010-09-02 | 2016-12-07 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | Ｌｐａ受容体アンタゴニストとしてのピラゾロピリジノン誘導体 |
| JP2015521183A (ja) | 2012-05-18 | 2015-07-27 | サノフイ | ピリジン誘導体および病理学的血栓形成に関連する状態の治療へのその使用 |
-
2013
- 2013-05-16 PL PL13723151T patent/PL2882715T3/pl unknown
- 2013-05-16 US US14/401,050 patent/US9346762B2/en not_active Expired - Fee Related
- 2013-05-16 PT PT137231510T patent/PT2882715T/pt unknown
- 2013-05-16 RU RU2014151360A patent/RU2645344C2/ru not_active IP Right Cessation
- 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 EP EP13723151.0A patent/EP2882715B1/en not_active Not-in-force
- 2013-05-16 SI SI201330499A patent/SI2882715T1/sl unknown
- 2013-05-16 KR KR20147033843A patent/KR20150010973A/ko not_active Ceased
- 2013-05-16 DK DK13723151.0T patent/DK2882715T3/en active
- 2013-05-16 HR HRP20170098TT patent/HRP20170098T1/hr unknown
- 2013-05-16 MX MX2014014011A patent/MX347615B/es active IP Right Grant
- 2013-05-16 HU HUE13723151A patent/HUE032890T2/hu unknown
- 2013-05-16 CN CN201380025967.9A patent/CN104302625B/zh not_active Expired - Fee Related
- 2013-05-16 AU AU2013261718A patent/AU2013261718B2/en not_active Ceased
- 2013-05-16 WO PCT/EP2013/060171 patent/WO2013171317A1/en not_active Ceased
- 2013-05-16 ES ES13723151.0T patent/ES2612205T3/es active Active
- 2013-05-16 LT LTEP13723151.0T patent/LT2882715T/lt unknown
- 2013-05-16 BR BR112014028406A patent/BR112014028406A2/pt not_active Application Discontinuation
- 2013-05-16 SG SG11201407210SA patent/SG11201407210SA/en unknown
-
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 |
|---|---|
| JP2015517514A (ja) | 2015-06-22 |
| PT2882715T (pt) | 2016-12-30 |
| EP2882715B1 (en) | 2016-11-09 |
| AU2013261718B2 (en) | 2017-10-19 |
| EP2882715A1 (en) | 2015-06-17 |
| SG11201407210SA (en) | 2014-12-30 |
| DK2882715T3 (en) | 2017-02-13 |
| CN104302625B (zh) | 2017-04-19 |
| CY1118618T1 (el) | 2017-07-12 |
| JP6257596B2 (ja) | 2018-01-10 |
| LT2882715T (lt) | 2017-02-10 |
| HRP20170098T1 (hr) | 2017-03-24 |
| US20150141477A1 (en) | 2015-05-21 |
| HUE032890T2 (hu) | 2017-11-28 |
| MX347615B (es) | 2017-05-04 |
| WO2013171317A1 (en) | 2013-11-21 |
| IL235221A (en) | 2016-06-30 |
| SI2882715T1 (sl) | 2017-03-31 |
| KR20150010973A (ko) | 2015-01-29 |
| RU2645344C2 (ru) | 2018-02-21 |
| MX2014014011A (es) | 2015-02-12 |
| CA2871542A1 (en) | 2013-11-21 |
| US9346762B2 (en) | 2016-05-24 |
| CN104302625A (zh) | 2015-01-21 |
| RU2014151360A (ru) | 2016-07-10 |
| PL2882715T3 (pl) | 2017-04-28 |
| AU2013261718A1 (en) | 2014-12-18 |
| BR112014028406A2 (pt) | 2017-06-27 |
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