CA2871542A1 - Pyrazole derivatives and their use as lpar5 antagonists - Google Patents
Pyrazole derivatives and their use as lpar5 antagonists Download PDFInfo
- Publication number
- CA2871542A1 CA2871542A1 CA2871542A CA2871542A CA2871542A1 CA 2871542 A1 CA2871542 A1 CA 2871542A1 CA 2871542 A CA2871542 A CA 2871542A CA 2871542 A CA2871542 A CA 2871542A CA 2871542 A1 CA2871542 A1 CA 2871542A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- series consisting
- phenyl
- methyl
- substituted
- 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.)
- Abandoned
Links
- 239000005557 antagonist Substances 0.000 title abstract description 9
- 150000003217 pyrazoles Chemical class 0.000 title description 25
- 150000001875 compounds Chemical class 0.000 claims abstract description 224
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 108
- 125000001424 substituent group Chemical group 0.000 claims description 85
- 239000001257 hydrogen Substances 0.000 claims description 78
- 229910052739 hydrogen Inorganic materials 0.000 claims description 78
- 150000003839 salts Chemical class 0.000 claims description 76
- 229910052736 halogen Inorganic materials 0.000 claims description 66
- 150000002367 halogens Chemical class 0.000 claims description 64
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 61
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 239000011737 fluorine Substances 0.000 claims description 38
- 229910052731 fluorine Inorganic materials 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 38
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 238000011282 treatment Methods 0.000 claims description 29
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 28
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- 125000001624 naphthyl group Chemical group 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 21
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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 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
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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 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
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Classifications
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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
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
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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
- C07D231/02—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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- 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)
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- Bioinformatics & Cheminformatics (AREA)
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- Engineering & Computer Science (AREA)
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- Hematology (AREA)
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- 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 | ||
| EP12305552.7 | 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 |
|---|---|
| CA2871542A1 true CA2871542A1 (en) | 2013-11-21 |
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Family Applications (1)
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| CA2871542A Abandoned CA2871542A1 (en) | 2012-05-18 | 2013-05-16 | Pyrazole derivatives and their use as lpar5 antagonists |
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| JP (1) | JP6257596B2 (https=) |
| KR (1) | KR20150010973A (https=) |
| CN (1) | CN104302625B (https=) |
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| 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=) |
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| 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 |
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| 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 |
| ES2612205T3 (es) | 2017-05-12 |
| 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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