JP2015521183A5 - - Google Patents
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- JP2015521183A5 JP2015521183A5 JP2015512071A JP2015512071A JP2015521183A5 JP 2015521183 A5 JP2015521183 A5 JP 2015521183A5 JP 2015512071 A JP2015512071 A JP 2015512071A JP 2015512071 A JP2015512071 A JP 2015512071A JP 2015521183 A5 JP2015521183 A5 JP 2015521183A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- series consisting
- phenyl
- methyl
- unsubstituted
- 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.)
- Ceased
Links
- 150000003839 salts Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 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
- 206010047249 Venous thrombosis 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
- 201000010875 transient cerebral ischemia Diseases 0.000 claims description 5
- 206010002388 Angina unstable Diseases 0.000 claims description 4
- 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
- 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
- 208000007814 Unstable Angina 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
- 201000004332 intermediate coronary syndrome Diseases 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
- 201000005060 thrombophlebitis Diseases 0.000 claims description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 3
- 206010014513 Embolism arterial Diseases 0.000 claims description 3
- 206010014522 Embolism venous 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
- 238000001356 surgical procedure Methods 0.000 claims description 3
- 230000002792 vascular Effects 0.000 claims description 3
- 208000004043 venous thromboembolism Diseases 0.000 claims description 3
- 206010003178 Arterial thrombosis Diseases 0.000 claims description 2
- 208000005189 Embolism Diseases 0.000 claims description 2
- 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 29
- 229910052739 hydrogen Inorganic materials 0.000 claims 15
- 239000001257 hydrogen Substances 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 7
- 229910052731 fluorine Inorganic materials 0.000 claims 7
- 239000011737 fluorine Substances 0.000 claims 7
- 150000002431 hydrogen Chemical class 0.000 claims 6
- 239000000203 mixture Substances 0.000 claims 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 230000009467 reduction Effects 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims 2
- 238000007887 coronary angioplasty Methods 0.000 claims 2
- 208000030175 lameness Diseases 0.000 claims 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 1
- SZPFUTNOQLTHBH-UHFFFAOYSA-N 2-[[2-[[5-(4-chlorophenyl)-2-methyl-6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]methoxy]-2-methylpropanoyl]amino]acetic acid Chemical compound C=1C=C(Cl)C=CC=1C=1C=C(COC(C)(C)C(=O)NCC(O)=O)C(C)=NC=1C1=CC=C(C(F)(F)F)C=C1 SZPFUTNOQLTHBH-UHFFFAOYSA-N 0.000 claims 1
- DTAULYNVXOAMJI-UHFFFAOYSA-N 2-[[5-(2,4-dichlorophenyl)-2-methyl-6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]methoxy]-2-methylpropanoic acid Chemical compound C=1C=C(Cl)C=C(Cl)C=1C=1C=C(COC(C)(C)C(O)=O)C(C)=NC=1C1=CC=C(C(F)(F)F)C=C1 DTAULYNVXOAMJI-UHFFFAOYSA-N 0.000 claims 1
- VUDHNUKDFQVSCU-UHFFFAOYSA-N 2-[[5-(2,4-dichlorophenyl)-2-methyl-6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]methoxy]acetic acid Chemical compound C=1C=C(Cl)C=C(Cl)C=1C=1C=C(COCC(O)=O)C(C)=NC=1C1=CC=C(C(F)(F)F)C=C1 VUDHNUKDFQVSCU-UHFFFAOYSA-N 0.000 claims 1
- KYGMPZHYVNWLLO-UHFFFAOYSA-N 2-[[5-(2,4-dichlorophenyl)-2-methyl-6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]methoxy]butanoic acid Chemical compound C=1C=C(C(F)(F)F)C=CC=1C=1N=C(C)C(COC(CC)C(O)=O)=CC=1C1=CC=C(Cl)C=C1Cl KYGMPZHYVNWLLO-UHFFFAOYSA-N 0.000 claims 1
- JUVJMKKHJXQIQR-UHFFFAOYSA-N 2-[[5-(2,4-dichlorophenyl)-2-methyl-6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]methoxy]propanoic acid Chemical compound C=1C=C(C(F)(F)F)C=CC=1C=1N=C(C)C(COC(C)C(O)=O)=CC=1C1=CC=C(Cl)C=C1Cl JUVJMKKHJXQIQR-UHFFFAOYSA-N 0.000 claims 1
- BYYVKZXQIFBNHD-UHFFFAOYSA-N 2-[[5-(4-chlorophenyl)-2-methyl-6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]methoxy]-2-methylpropanoic acid Chemical compound C=1C=C(Cl)C=CC=1C=1C=C(COC(C)(C)C(O)=O)C(C)=NC=1C1=CC=C(C(F)(F)F)C=C1 BYYVKZXQIFBNHD-UHFFFAOYSA-N 0.000 claims 1
- WLIWTXBFHFJDTR-UHFFFAOYSA-N 2-[[5-(4-chlorophenyl)-2-methyl-6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]methoxy]acetic acid Chemical compound C=1C=C(Cl)C=CC=1C=1C=C(COCC(O)=O)C(C)=NC=1C1=CC=C(C(F)(F)F)C=C1 WLIWTXBFHFJDTR-UHFFFAOYSA-N 0.000 claims 1
- ACOAIPGIQZYWFW-UHFFFAOYSA-N 2-[[5-(4-chlorophenyl)-2-methyl-6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]methoxy]butanoic acid Chemical compound C=1C=C(C(F)(F)F)C=CC=1C=1N=C(C)C(COC(CC)C(O)=O)=CC=1C1=CC=C(Cl)C=C1 ACOAIPGIQZYWFW-UHFFFAOYSA-N 0.000 claims 1
- IEKBAJLPLDDIQO-UHFFFAOYSA-N 2-[[5-(4-chlorophenyl)-2-methyl-6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]methoxy]propanoic acid Chemical compound C=1C=C(C(F)(F)F)C=CC=1C=1N=C(C)C(COC(C)C(O)=O)=CC=1C1=CC=C(Cl)C=C1 IEKBAJLPLDDIQO-UHFFFAOYSA-N 0.000 claims 1
- HQOYTDBBASBTGN-UHFFFAOYSA-N 3-[[2-[[5-(4-chlorophenyl)-2-methyl-6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]methoxy]-2-methylpropanoyl]amino]propanoic acid Chemical compound C=1C=C(Cl)C=CC=1C=1C=C(COC(C)(C)C(=O)NCCC(O)=O)C(C)=NC=1C1=CC=C(C(F)(F)F)C=C1 HQOYTDBBASBTGN-UHFFFAOYSA-N 0.000 claims 1
- CQXWPFBKVJYFJY-UHFFFAOYSA-N 4-[2-[[5-(2,4-dichlorophenyl)-2-methyl-6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]methoxy]propanoylamino]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1NC(=O)C(C)OCC(C(=NC=1C=2C=CC(=CC=2)C(F)(F)F)C)=CC=1C1=CC=C(Cl)C=C1Cl CQXWPFBKVJYFJY-UHFFFAOYSA-N 0.000 claims 1
- DMFVFPYUDJJUSC-UHFFFAOYSA-N 4-[[[2-[[5-(2,4-dichlorophenyl)-2-methyl-6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]methoxy]-2-methylpropanoyl]amino]methyl]benzoic acid Chemical compound C=1C=C(Cl)C=C(Cl)C=1C=1C=C(COC(C)(C)C(=O)NCC=2C=CC(=CC=2)C(O)=O)C(C)=NC=1C1=CC=C(C(F)(F)F)C=C1 DMFVFPYUDJJUSC-UHFFFAOYSA-N 0.000 claims 1
- BPSIFSLPSYVFID-UHFFFAOYSA-N 4-[[[2-[[5-(4-chlorophenyl)-2-methyl-6-[4-(trifluoromethyl)phenyl]pyridin-3-yl]methoxy]-2-methylpropanoyl]amino]methyl]benzoic acid Chemical compound C=1C=C(Cl)C=CC=1C=1C=C(COC(C)(C)C(=O)NCC=2C=CC(=CC=2)C(O)=O)C(C)=NC=1C1=CC=C(C(F)(F)F)C=C1 BPSIFSLPSYVFID-UHFFFAOYSA-N 0.000 claims 1
- RGBKIWUQPQVIDM-UHFFFAOYSA-N 4-[[[2-[[6-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-2-methylpyridin-3-yl]methoxy]-2-methylpropanoyl]amino]methyl]benzoic acid Chemical compound C=1C=C(Cl)C=C(Cl)C=1C=1C=C(COC(C)(C)C(=O)NCC=2C=CC(=CC=2)C(O)=O)C(C)=NC=1C1=CC=C(Cl)C=C1 RGBKIWUQPQVIDM-UHFFFAOYSA-N 0.000 claims 1
- 206010053567 Coagulopathies Diseases 0.000 claims 1
- 208000016192 Demyelinating disease 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
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 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
- 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
- 238000012423 maintenance Methods 0.000 claims 1
- 230000006724 microglial activation Effects 0.000 claims 1
- 125000001624 naphthyl group Chemical group 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
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 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
- 239000000651 prodrug Substances 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 206010043561 Thrombocytopenic purpura Diseases 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
- 208000019622 heart disease Diseases 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
- 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 |
|---|---|---|---|
| EP12305551.9 | 2012-05-18 | ||
| EP12305551 | 2012-05-18 | ||
| PCT/EP2013/060169 WO2013171316A1 (en) | 2012-05-18 | 2013-05-16 | Pyridine derivatives and their use in the treatment of conditions associated with pathological thrombus formation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015521183A JP2015521183A (ja) | 2015-07-27 |
| JP2015521183A5 true JP2015521183A5 (OSRAM) | 2016-06-23 |
Family
ID=48446367
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015512071A Ceased JP2015521183A (ja) | 2012-05-18 | 2013-05-16 | 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 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US9346757B2 (OSRAM) |
| EP (1) | EP2850062B1 (OSRAM) |
| JP (1) | JP2015521183A (OSRAM) |
| WO (1) | WO2013171316A1 (OSRAM) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP6257596B2 (ja) | 2012-05-18 | 2018-01-10 | サノフイ | 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 |
| JP7118642B2 (ja) | 2014-08-08 | 2022-08-16 | アリ リサーチ ソシエタ ア レスポンサビリタ リミタータ センプリフィカタ | 炎症性およびアレルギー性病変の治療に用いるための脂肪酸とパルミトイルエタノールアミドの混合物 |
| IL291783A (en) | 2019-10-02 | 2022-06-01 | Domain Therapeutics | ep4 prostaglandin e2 receptor antagonists |
| GB201914585D0 (en) | 2019-10-09 | 2019-11-20 | Heptares Therapeutics Ltd | Prostaglandin ep4 receptor antagonist compounds |
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 |
| PT1258484E (pt) * | 2000-02-18 | 2009-04-03 | Kyowa Hakko Kirin Co Ltd | Novos compostos de isoxazol e de tiazol e sua utilização enquanto fármacos |
| 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 |
| 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 |
| JP6257596B2 (ja) | 2012-05-18 | 2018-01-10 | サノフイ | 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 |
-
2013
- 2013-05-16 US US14/401,056 patent/US9346757B2/en not_active Expired - Fee Related
- 2013-05-16 EP EP13723150.2A patent/EP2850062B1/en not_active Not-in-force
- 2013-05-16 WO PCT/EP2013/060169 patent/WO2013171316A1/en not_active Ceased
- 2013-05-16 JP JP2015512071A patent/JP2015521183A/ja not_active Ceased
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