JP2015517514A5 - - Google Patents
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- Publication number
- JP2015517514A5 JP2015517514A5 JP2015512072A JP2015512072A JP2015517514A5 JP 2015517514 A5 JP2015517514 A5 JP 2015517514A5 JP 2015512072 A JP2015512072 A JP 2015512072A JP 2015512072 A JP2015512072 A JP 2015512072A JP 2015517514 A5 JP2015517514 A5 JP 2015517514A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- series consisting
- phenyl
- unsubstituted
- methyl
- 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.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 206010002388 Angina unstable Diseases 0.000 claims description 5
- 208000010378 Pulmonary Embolism Diseases 0.000 claims description 5
- 208000007536 Thrombosis Diseases 0.000 claims description 5
- 208000032109 Transient ischaemic attack Diseases 0.000 claims description 5
- 208000007814 Unstable Angina Diseases 0.000 claims description 5
- 206010000891 acute myocardial infarction Diseases 0.000 claims description 5
- 230000005764 inhibitory process Effects 0.000 claims description 5
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 5
- 201000010875 transient cerebral ischemia Diseases 0.000 claims description 5
- 206010008088 Cerebral artery embolism Diseases 0.000 claims description 4
- 206010008092 Cerebral artery thrombosis Diseases 0.000 claims description 4
- 206010011091 Coronary artery thrombosis Diseases 0.000 claims description 4
- 206010051055 Deep vein thrombosis Diseases 0.000 claims description 4
- 206010014513 Embolism arterial Diseases 0.000 claims description 4
- 206010014522 Embolism venous Diseases 0.000 claims description 4
- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 4
- 206010063544 Renal embolism Diseases 0.000 claims description 4
- 208000007718 Stable Angina Diseases 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- 206010047249 Venous thrombosis Diseases 0.000 claims description 4
- 230000033115 angiogenesis Effects 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 208000002528 coronary thrombosis Diseases 0.000 claims description 4
- 208000009190 disseminated intravascular coagulation Diseases 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 201000010849 intracranial embolism Diseases 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 201000011461 pre-eclampsia Diseases 0.000 claims description 4
- 208000037803 restenosis Diseases 0.000 claims description 4
- 238000001356 surgical procedure Methods 0.000 claims description 4
- 201000005060 thrombophlebitis Diseases 0.000 claims description 4
- 208000004043 venous thromboembolism Diseases 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 208000004454 Hyperalgesia Diseases 0.000 claims description 3
- 208000035154 Hyperesthesia Diseases 0.000 claims description 3
- 206010065390 Inflammatory pain Diseases 0.000 claims description 3
- 208000001435 Thromboembolism Diseases 0.000 claims description 3
- 201000007023 Thrombotic Thrombocytopenic Purpura Diseases 0.000 claims description 3
- 208000026935 allergic disease Diseases 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 230000002792 vascular Effects 0.000 claims description 3
- 101001038037 Homo sapiens Lysophosphatidic acid receptor 5 Proteins 0.000 claims description 2
- 230000001575 pathological effect Effects 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 25
- 125000001424 substituent group Chemical group 0.000 claims 18
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 9
- 229910052731 fluorine Inorganic materials 0.000 claims 9
- 239000011737 fluorine Substances 0.000 claims 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000001153 fluoro group Chemical group F* 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 125000003118 aryl group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000005842 heteroatom Chemical group 0.000 claims 5
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 5
- 125000001624 naphthyl group Chemical group 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 230000009467 reduction Effects 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- IDCXLYCLPHRSAZ-UHFFFAOYSA-N 1,5-diphenylpyrazole Chemical compound C=1C=CC=CC=1N1N=CC=C1C1=CC=CC=C1 IDCXLYCLPHRSAZ-UHFFFAOYSA-N 0.000 claims 1
- ABGFOJMIZGSODH-UHFFFAOYSA-N 4-[2-[(1,3-diphenylpyrazol-4-yl)methoxy]propanoylamino]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1NC(=O)C(C)OCC1=CN(C=2C=CC=CC=2)N=C1C1=CC=CC=C1 ABGFOJMIZGSODH-UHFFFAOYSA-N 0.000 claims 1
- IZJQAPIUSXCKBZ-UHFFFAOYSA-N 4-[2-[(1-phenyl-3-thiophen-2-ylpyrazol-4-yl)methoxy]propanoylamino]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1NC(=O)C(C)OCC1=CN(C=2C=CC=CC=2)N=C1C1=CC=CS1 IZJQAPIUSXCKBZ-UHFFFAOYSA-N 0.000 claims 1
- YMKUHISAVZTWIB-UHFFFAOYSA-N 4-[2-[(3,5-dimethyl-1-phenylpyrazol-4-yl)methoxy]propanoylamino]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1NC(=O)C(C)OCC(=C1C)C(C)=NN1C1=CC=CC=C1 YMKUHISAVZTWIB-UHFFFAOYSA-N 0.000 claims 1
- DYFZSMCIWRJDNT-UHFFFAOYSA-N 4-[2-[(3-naphthalen-2-yl-1-phenylpyrazol-4-yl)methoxy]propanoylamino]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1NC(=O)C(C)OCC(C(=N1)C=2C=C3C=CC=CC3=CC=2)=CN1C1=CC=CC=C1 DYFZSMCIWRJDNT-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- CCWMBJVUEFANKE-UHFFFAOYSA-N 4-[2-[[1-(2-chlorophenyl)-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=CC=2)Cl)C=1C1=CC=C(C(F)(F)F)C=C1 CCWMBJVUEFANKE-UHFFFAOYSA-N 0.000 claims 1
- ALCUPGQAVZDLII-UHFFFAOYSA-N 4-[2-[[1-(4-chlorophenyl)-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)C=1C1=CC=C(C(F)(F)F)C=C1 ALCUPGQAVZDLII-UHFFFAOYSA-N 0.000 claims 1
- MFXKTKIMAKKXQB-UHFFFAOYSA-N 4-[2-[[1-benzyl-3-(3-methoxyphenyl)pyrazol-4-yl]methoxy]propanoylamino]benzoic acid Chemical compound COC1=CC=CC(C=2C(=CN(CC=3C=CC=CC=3)N=2)COC(C)C(=O)NC=2C=CC(=CC=2)C(O)=O)=C1 MFXKTKIMAKKXQB-UHFFFAOYSA-N 0.000 claims 1
- CHQRCYBSUQRSHF-UHFFFAOYSA-N 4-[2-[[3-(4-cyclohexylphenyl)-1-phenylpyrazol-4-yl]methoxy]propanoylamino]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1NC(=O)C(C)OCC1=CN(C=2C=CC=CC=2)N=C1C(C=C1)=CC=C1C1CCCCC1 CHQRCYBSUQRSHF-UHFFFAOYSA-N 0.000 claims 1
- QHNMUNOKXNNTRY-UHFFFAOYSA-N 4-[2-[[5-(4-fluorophenoxy)-1-methyl-3-phenylpyrazol-4-yl]methoxy]propanoylamino]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1NC(=O)C(C)OCC(C(=NN1C)C=2C=CC=CC=2)=C1OC1=CC=C(F)C=C1 QHNMUNOKXNNTRY-UHFFFAOYSA-N 0.000 claims 1
- OGXXWCVIIYQBHL-UHFFFAOYSA-N 4-[[2-[[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]methoxy]-3-methylbutanoyl]amino]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1NC(=O)C(C(C)C)OCC(C=1C)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 OGXXWCVIIYQBHL-UHFFFAOYSA-N 0.000 claims 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 claims 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 claims 1
- DCSCGGYEUWOGTN-UHFFFAOYSA-N 4-[[[2-[[1-(2,4-dichlorophenyl)-4-methyl-5-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]methoxy]-2-methylpropanoyl]amino]methyl]benzoic acid Chemical compound N=1N(C=2C(=CC(Cl)=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 DCSCGGYEUWOGTN-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- LCYJQOFLLJVAEZ-UHFFFAOYSA-N 4-[[[2-[[1-(4-chlorophenyl)-4-methyl-5-[4-(trifluoromethyl)phenyl]pyrazol-3-yl]methoxy]-2-methylpropanoyl]amino]methyl]benzoic acid Chemical compound N=1N(C=2C=CC(Cl)=CC=2)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 LCYJQOFLLJVAEZ-UHFFFAOYSA-N 0.000 claims 1
- CTJSGOVQEXDBFJ-UHFFFAOYSA-N 4-[[[2-[[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazol-3-yl]methoxy]-2-methylpropanoyl]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=1COC(C)(C)C(=O)NCC1=CC=C(C(O)=O)C=C1 CTJSGOVQEXDBFJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 206010003178 Arterial thrombosis Diseases 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- 206010053567 Coagulopathies Diseases 0.000 claims 1
- 208000016192 Demyelinating disease Diseases 0.000 claims 1
- 208000005189 Embolism Diseases 0.000 claims 1
- 208000035895 Guillain-Barré syndrome Diseases 0.000 claims 1
- 206010049567 Miller Fisher syndrome Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 208000029067 Neuromyelitis optica spectrum disease Diseases 0.000 claims 1
- 208000003435 Optic Neuritis Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 206010057469 Vascular stenosis Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 230000003187 abdominal effect Effects 0.000 claims 1
- 230000002159 abnormal effect Effects 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 210000001367 artery Anatomy 0.000 claims 1
- 230000007214 atherothrombosis Effects 0.000 claims 1
- 208000015294 blood coagulation disease Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 230000020411 cell activation Effects 0.000 claims 1
- 210000003169 central nervous system Anatomy 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 230000009852 coagulant defect Effects 0.000 claims 1
- 238000007887 coronary angioplasty Methods 0.000 claims 1
- 230000003210 demyelinating effect Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000001631 haemodialysis Methods 0.000 claims 1
- 230000000322 hemodialysis Effects 0.000 claims 1
- 210000003630 histaminocyte Anatomy 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 210000003127 knee Anatomy 0.000 claims 1
- 230000007774 longterm Effects 0.000 claims 1
- 210000003141 lower extremity Anatomy 0.000 claims 1
- 238000012423 maintenance Methods 0.000 claims 1
- 230000006724 microglial activation Effects 0.000 claims 1
- 208000008795 neuromyelitis optica Diseases 0.000 claims 1
- 201000001119 neuropathy Diseases 0.000 claims 1
- 230000007823 neuropathy Effects 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 210000001428 peripheral nervous system Anatomy 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 230000002537 thrombolytic effect Effects 0.000 claims 1
- 208000009174 transverse myelitis Diseases 0.000 claims 1
- 210000005166 vasculature Anatomy 0.000 claims 1
- 210000003462 vein Anatomy 0.000 claims 1
- 238000007891 venous angioplasty Methods 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- 230000002265 prevention Effects 0.000 description 3
- 230000001732 thrombotic effect Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 2
- 206010020751 Hypersensitivity Diseases 0.000 description 1
- 206010043561 Thrombocytopenic purpura Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 238000002399 angioplasty Methods 0.000 description 1
- 238000013172 carotid endarterectomy Methods 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 230000003073 embolic effect Effects 0.000 description 1
- 230000028709 inflammatory response Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000010118 platelet activation Effects 0.000 description 1
- 230000018127 platelet degranulation Effects 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12305552 | 2012-05-18 | ||
| EP12305552.7 | 2012-05-18 | ||
| PCT/EP2013/060171 WO2013171317A1 (en) | 2012-05-18 | 2013-05-16 | Pyrazole derivatives and their use as lpar5 antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015517514A JP2015517514A (ja) | 2015-06-22 |
| JP2015517514A5 true JP2015517514A5 (enExample) | 2016-06-23 |
| JP6257596B2 JP6257596B2 (ja) | 2018-01-10 |
Family
ID=48446368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015512072A Expired - Fee Related JP6257596B2 (ja) | 2012-05-18 | 2013-05-16 | ピラゾール誘導体およびｌｐａｒ５アンタゴニストとしてのその使用 |
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) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9346757B2 (en) | 2012-05-18 | 2016-05-24 | Sanofi | Pyridine derivatives and their use in the treatment of conditions associated with pathological thrombus formation |
| AU2016277126A1 (en) * | 2015-06-12 | 2017-12-14 | Vettore, LLC | MCT4 inhibitors for treating disease |
| CN110114351B (zh) * | 2016-12-12 | 2022-09-20 | 维托尔股份有限公司 | Mct4的杂环抑制剂 |
| IL291783A (en) | 2019-10-02 | 2022-06-01 | Domain Therapeutics | ep4 prostaglandin e2 receptor antagonists |
| 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 |
| CA2495939A1 (en) | 2002-09-04 | 2004-03-18 | Merck Frosst Canada & Co./Merck Frosst Canada & Cie | Cathepsin cysteine protease inhibitors |
| MX2009008103A (es) | 2007-02-09 | 2009-08-18 | Takeda Pharmaceutical | Compuestos anulares fusionados como agonistas parciales de prar-gamma. |
| JP5560202B2 (ja) | 2007-12-26 | 2014-07-23 | サノフイ | Ｐ２ｙ１２拮抗薬としてのピラゾール−カルボキサミド誘導体 |
| EP2262778B8 (en) | 2008-03-07 | 2020-01-01 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.p.A. | 1-benzyl-3-hydroxymethylindazole derivatives and use thereof in the treatment of diseases based on the expression of mcp-1, cx3cr1 and p40 |
| KR101581828B1 (ko) * | 2008-03-07 | 2015-12-31 | 아지엔드 키미쉐 리유나이트 안젤리니 프란체스코 에이.씨.알.에이.에프. 에스.피.에이 | 신규한 1-벤질-3-하이드록시메틸인다졸 유도체들 및 ｍｃｐ-1, ｃｘ3ｃｒ1 및 ｐ40의 발현을 기초로 한 질환들의 치료에서 이의 용도 |
| EP2408762A1 (fr) * | 2009-03-19 | 2012-01-25 | Sanofi | Derives d'indazole inhibiteurs d'hsp90, compositions les contenant et utilisation |
| SG176885A1 (en) * | 2009-08-03 | 2012-01-30 | Acraf | Process for the preparation of 1-benzyl-3-hydr0xymethyl-1h-indaz0le and its derivatives and required magnesium intermediates |
| EP2611808B1 (en) * | 2010-09-02 | 2014-11-12 | Merck Patent GmbH | Pyrazolopyridinone derivatives as lpa receptor antagonists |
| US9346757B2 (en) | 2012-05-18 | 2016-05-24 | Sanofi | Pyridine derivatives and their use in the treatment of conditions associated with pathological thrombus formation |
-
2013
- 2013-05-16 JP JP2015512072A patent/JP6257596B2/ja not_active Expired - Fee Related
- 2013-05-16 US US14/401,050 patent/US9346762B2/en not_active Expired - Fee Related
- 2013-05-16 HU HUE13723151A patent/HUE032890T2/hu unknown
- 2013-05-16 HR HRP20170098TT patent/HRP20170098T1/hr unknown
- 2013-05-16 CA CA2871542A patent/CA2871542A1/en not_active Abandoned
- 2013-05-16 RU RU2014151360A patent/RU2645344C2/ru not_active IP Right Cessation
- 2013-05-16 DK DK13723151.0T patent/DK2882715T3/en active
- 2013-05-16 LT LTEP13723151.0T patent/LT2882715T/lt unknown
- 2013-05-16 SI SI201330499A patent/SI2882715T1/sl unknown
- 2013-05-16 KR KR20147033843A patent/KR20150010973A/ko not_active Ceased
- 2013-05-16 AU AU2013261718A patent/AU2013261718B2/en not_active Ceased
- 2013-05-16 PT PT137231510T patent/PT2882715T/pt unknown
- 2013-05-16 BR BR112014028406A patent/BR112014028406A2/pt not_active Application Discontinuation
- 2013-05-16 PL PL13723151T patent/PL2882715T3/pl unknown
- 2013-05-16 SG SG11201407210SA patent/SG11201407210SA/en unknown
- 2013-05-16 ES ES13723151.0T patent/ES2612205T3/es active Active
- 2013-05-16 CN CN201380025967.9A patent/CN104302625B/zh not_active Expired - Fee Related
- 2013-05-16 MX MX2014014011A patent/MX347615B/es active IP Right Grant
- 2013-05-16 WO PCT/EP2013/060171 patent/WO2013171317A1/en not_active Ceased
- 2013-05-16 EP EP13723151.0A patent/EP2882715B1/en not_active Not-in-force
-
2014
- 2014-10-20 IL IL235221A patent/IL235221A/en active IP Right Grant
-
2017
- 2017-02-08 CY CY20171100175T patent/CY1118618T1/el unknown
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