DK2882715T3 - PYRAZOL DERIVATIVES AND USE THEREOF AS LPAR5 ANTAGONISTS - Google Patents
PYRAZOL DERIVATIVES AND USE THEREOF AS LPAR5 ANTAGONISTS Download PDFInfo
- Publication number
- DK2882715T3 DK2882715T3 DK13723151.0T DK13723151T DK2882715T3 DK 2882715 T3 DK2882715 T3 DK 2882715T3 DK 13723151 T DK13723151 T DK 13723151T DK 2882715 T3 DK2882715 T3 DK 2882715T3
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- DK
- Denmark
- Prior art keywords
- alkyl
- series consisting
- cycloalkyl
- substituted
- unsubstituted
- Prior art date
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- 101001038037 Homo sapiens Lysophosphatidic acid receptor 5 Proteins 0.000 title claims description 53
- 102100040404 Lysophosphatidic acid receptor 5 Human genes 0.000 title description 27
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical class C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 title description 14
- 239000005557 antagonist Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims description 203
- 125000001424 substituent group Chemical group 0.000 claims description 86
- 239000001257 hydrogen Substances 0.000 claims description 85
- 229910052739 hydrogen Inorganic materials 0.000 claims description 85
- 229910052736 halogen Inorganic materials 0.000 claims description 65
- 150000003839 salts Chemical class 0.000 claims description 65
- 150000002367 halogens Chemical class 0.000 claims description 63
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 58
- 125000001153 fluoro group Chemical group F* 0.000 claims description 54
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 47
- 210000003630 histaminocyte Anatomy 0.000 claims description 42
- -1 3-naphthalen-2-yl-1-phenyl-1H-pyrazol-4-ylmethoxy Chemical group 0.000 claims description 41
- 239000000203 mixture Substances 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 229910052760 oxygen Inorganic materials 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 230000015572 biosynthetic process Effects 0.000 claims description 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 34
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- 230000004913 activation Effects 0.000 claims description 30
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 150000002431 hydrogen Chemical class 0.000 claims description 25
- 230000005764 inhibitory process Effects 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 25
- 238000011282 treatment Methods 0.000 claims description 25
- 125000001624 naphthyl group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 229910052717 sulfur Inorganic materials 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 19
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
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- 210000000274 microglia Anatomy 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
- 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 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 9
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- IBMXKBVMTCSNKI-UHFFFAOYSA-N 4-[2-[[1-(2,4-dichlorophenyl)-4-methyl-5-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]methoxy]propanoylamino]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1NC(=O)C(C)OCC(C=1C)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(C(F)(F)F)C=C1 IBMXKBVMTCSNKI-UHFFFAOYSA-N 0.000 claims description 5
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- ZSAVBGWQPLJKJE-UHFFFAOYSA-N 4-[2-[(1,5-diphenylpyrazol-3-yl)methoxy]propanoylamino]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1NC(=O)C(C)OCC(=NN1C=2C=CC=CC=2)C=C1C1=CC=CC=C1 ZSAVBGWQPLJKJE-UHFFFAOYSA-N 0.000 claims description 4
- 206010008088 Cerebral artery embolism Diseases 0.000 claims description 4
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- 208000009190 disseminated intravascular coagulation Diseases 0.000 claims description 4
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- 201000005060 thrombophlebitis Diseases 0.000 claims description 4
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- 208000004043 venous thromboembolism Diseases 0.000 claims description 4
- ZKTHTEMISGYELR-UHFFFAOYSA-N 4-[[[2-[[1-(2-chlorophenyl)-4-methyl-5-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]methoxy]-2-methylpropanoyl]amino]methyl]benzoic acid Chemical compound N=1N(C=2C(=CC=CC=2)Cl)C(C=2C=CC(=CC=2)C(F)(F)F)=C(C)C=1COC(C)(C)C(=O)NCC1=CC=C(C(O)=O)C=C1 ZKTHTEMISGYELR-UHFFFAOYSA-N 0.000 claims description 3
- CPNUSDXKJSBWKD-UHFFFAOYSA-N 4-[[[2-[[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]methoxy]acetyl]amino]methyl]benzoic acid Chemical compound N=1N(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Cl)=CC=2)=C(C)C=1COCC(=O)NCC1=CC=C(C(O)=O)C=C1 CPNUSDXKJSBWKD-UHFFFAOYSA-N 0.000 claims description 3
- 206010003178 Arterial thrombosis Diseases 0.000 claims description 3
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- 208000037803 restenosis Diseases 0.000 claims description 3
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- CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 208000030939 Chronic inflammatory demyelinating polyneuropathy Diseases 0.000 claims description 2
- 208000005189 Embolism Diseases 0.000 claims description 2
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims description 2
- 206010022562 Intermittent claudication Diseases 0.000 claims description 2
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 208000003435 Optic Neuritis Diseases 0.000 claims description 2
- 206010040070 Septic Shock Diseases 0.000 claims description 2
- 208000036142 Viral infection Diseases 0.000 claims description 2
- 230000002159 abnormal effect Effects 0.000 claims description 2
- 210000001367 artery Anatomy 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims description 2
- 201000005795 chronic inflammatory demyelinating polyneuritis Diseases 0.000 claims description 2
- 238000007887 coronary angioplasty Methods 0.000 claims description 2
- 238000001631 haemodialysis Methods 0.000 claims description 2
- 230000000322 hemodialysis Effects 0.000 claims description 2
- 210000003127 knee Anatomy 0.000 claims description 2
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- 238000012423 maintenance Methods 0.000 claims description 2
- 208000008795 neuromyelitis optica Diseases 0.000 claims description 2
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- 238000007891 venous angioplasty Methods 0.000 claims description 2
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 127
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 17
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 8
- QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims 1
- GNNKYEUYWBUEFD-UHFFFAOYSA-N 1-phenyl-3-thiophen-2-ylpyrazole Chemical compound C1=CSC(C2=NN(C=C2)C=2C=CC=CC=2)=C1 GNNKYEUYWBUEFD-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- MNOULQLXILYKNV-UHFFFAOYSA-N 5-[4-(trifluoromethyl)phenyl]-1h-pyrazole Chemical group C1=CC(C(F)(F)F)=CC=C1C1=CC=NN1 MNOULQLXILYKNV-UHFFFAOYSA-N 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
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- 230000002526 effect on cardiovascular system Effects 0.000 claims 1
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- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 60
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Classifications
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- 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
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- 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
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- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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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
- C07D231/54—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
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- 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
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
|---|---|
| DK2882715T3 true DK2882715T3 (en) | 2017-02-13 |
Family
ID=48446368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK13723151.0T DK2882715T3 (en) | 2012-05-18 | 2013-05-16 | PYRAZOL DERIVATIVES AND USE THEREOF AS LPAR5 ANTAGONISTS |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US9346762B2 (enExample) |
| EP (1) | EP2882715B1 (enExample) |
| JP (1) | JP6257596B2 (enExample) |
| KR (1) | KR20150010973A (enExample) |
| CN (1) | CN104302625B (enExample) |
| AU (1) | AU2013261718B2 (enExample) |
| BR (1) | BR112014028406A2 (enExample) |
| CA (1) | CA2871542A1 (enExample) |
| CY (1) | CY1118618T1 (enExample) |
| DK (1) | DK2882715T3 (enExample) |
| ES (1) | ES2612205T3 (enExample) |
| HR (1) | HRP20170098T1 (enExample) |
| HU (1) | HUE032890T2 (enExample) |
| IL (1) | IL235221A (enExample) |
| LT (1) | LT2882715T (enExample) |
| MX (1) | MX347615B (enExample) |
| PL (1) | PL2882715T3 (enExample) |
| PT (1) | PT2882715T (enExample) |
| RU (1) | RU2645344C2 (enExample) |
| SG (1) | SG11201407210SA (enExample) |
| SI (1) | SI2882715T1 (enExample) |
| WO (1) | WO2013171317A1 (enExample) |
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| 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 |
| AU2016277126A1 (en) * | 2015-06-12 | 2017-12-14 | Vettore, LLC | MCT4 inhibitors for treating disease |
| BR112019011825A2 (pt) | 2016-12-12 | 2019-10-22 | Vettore, LLC | composto, enantiômero isolado, composição farmacêutica, método para inibir a atividade do transportador de monocarboxilato mct4, ou um mutante do mesmo, em uma amostra biológica, método para inibir a atividade do transportador de monocarboxilato mct4, ou um mutante do mesmo, em relação ao transportador de monocarboxilato mct1, ou um mutante do mesmo, em um paciente, método para tratar um distúrbio mediado por transportador de monocarboxilato mct4 em um sujeito que necessite do mesmo, uso de um composto e método para obter um efeito em um paciente |
| KR20220077140A (ko) | 2019-10-02 | 2022-06-08 | 도메인 테라퓨틱스 | 프로스타글란딘 e2(pge2) ep4 수용체 길항제 |
| 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 |
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| 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 |
| AU2008215490A1 (en) | 2007-02-09 | 2008-08-21 | Takeda Pharmaceutical Company Limited | Fused ring compounds as partial agonists of PPAR-gamma |
| EP2238127B1 (en) | 2007-12-26 | 2012-08-15 | Sanofi | Pyrazole-carboxamide derivatives as p2y12 antagonists |
| DK2254869T3 (en) | 2008-03-07 | 2017-09-04 | Acraf | 1-BENZYL-3-HYDROXYMETHYL INDAZOLE DERIVATIVES AND USE THEREOF IN THE TREATMENT OF DISEASES BASED ON THE EXPRESSION OF CX3CR1 AND P40 |
| MX2010009625A (es) | 2008-03-07 | 2010-09-28 | Acraf | Derivados de 1-bencil-3-hidroximetilindazol y uso de los mismos en el tratamiento de enfermedades basadas en la expresion de mcp-1, cx3cr1 y p40. |
| AU2010224652A1 (en) * | 2009-03-19 | 2011-10-13 | Sanofi | Hsp90 inhibiting indazole derivatives, compositions containing same and use thereof |
| BR112012002130A2 (pt) * | 2009-08-03 | 2015-09-15 | Aziende Chimique Riunite Angelini Francesco A C R A F S P A | processo para a preparação de composto,e, composto intermediário |
| 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 |
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2013
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- 2013-05-16 HU HUE13723151A patent/HUE032890T2/hu unknown
- 2013-05-16 HR HRP20170098TT patent/HRP20170098T1/hr unknown
- 2013-05-16 AU AU2013261718A patent/AU2013261718B2/en not_active Ceased
- 2013-05-16 MX MX2014014011A patent/MX347615B/es active IP Right Grant
- 2013-05-16 PT PT137231510T patent/PT2882715T/pt unknown
- 2013-05-16 ES ES13723151.0T patent/ES2612205T3/es active Active
- 2013-05-16 BR BR112014028406A patent/BR112014028406A2/pt not_active Application Discontinuation
- 2013-05-16 KR KR20147033843A patent/KR20150010973A/ko not_active Ceased
- 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 SG SG11201407210SA patent/SG11201407210SA/en unknown
- 2013-05-16 PL PL13723151T patent/PL2882715T3/pl unknown
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- 2013-05-16 US US14/401,050 patent/US9346762B2/en not_active Expired - Fee Related
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|---|---|
| EP2882715A1 (en) | 2015-06-17 |
| MX2014014011A (es) | 2015-02-12 |
| RU2014151360A (ru) | 2016-07-10 |
| AU2013261718A1 (en) | 2014-12-18 |
| CN104302625B (zh) | 2017-04-19 |
| BR112014028406A2 (pt) | 2017-06-27 |
| CN104302625A (zh) | 2015-01-21 |
| CY1118618T1 (el) | 2017-07-12 |
| US9346762B2 (en) | 2016-05-24 |
| AU2013261718B2 (en) | 2017-10-19 |
| WO2013171317A1 (en) | 2013-11-21 |
| HUE032890T2 (hu) | 2017-11-28 |
| PL2882715T3 (pl) | 2017-04-28 |
| LT2882715T (lt) | 2017-02-10 |
| PT2882715T (pt) | 2016-12-30 |
| RU2645344C2 (ru) | 2018-02-21 |
| JP2015517514A (ja) | 2015-06-22 |
| IL235221A (en) | 2016-06-30 |
| CA2871542A1 (en) | 2013-11-21 |
| US20150141477A1 (en) | 2015-05-21 |
| HRP20170098T1 (hr) | 2017-03-24 |
| JP6257596B2 (ja) | 2018-01-10 |
| MX347615B (es) | 2017-05-04 |
| SI2882715T1 (sl) | 2017-03-31 |
| KR20150010973A (ko) | 2015-01-29 |
| EP2882715B1 (en) | 2016-11-09 |
| ES2612205T3 (es) | 2017-05-12 |
| SG11201407210SA (en) | 2014-12-30 |
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