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
- A61K31/415—1,2-Diazoles
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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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
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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
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Epidemiology (AREA)
- Neurology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Vascular Medicine (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Urology & Nephrology (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 |
Family
ID=48446368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2871542A Abandoned CA2871542A1 (en) | 2012-05-18 | 2013-05-16 | Pyrazole derivatives and their use as lpar5 antagonists |
Country Status (22)
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|---|---|
| US (1) | US9346762B2 (OSRAM) |
| EP (1) | EP2882715B1 (OSRAM) |
| JP (1) | JP6257596B2 (OSRAM) |
| KR (1) | KR20150010973A (OSRAM) |
| CN (1) | CN104302625B (OSRAM) |
| AU (1) | AU2013261718B2 (OSRAM) |
| BR (1) | BR112014028406A2 (OSRAM) |
| CA (1) | CA2871542A1 (OSRAM) |
| CY (1) | CY1118618T1 (OSRAM) |
| DK (1) | DK2882715T3 (OSRAM) |
| ES (1) | ES2612205T3 (OSRAM) |
| HR (1) | HRP20170098T1 (OSRAM) |
| HU (1) | HUE032890T2 (OSRAM) |
| IL (1) | IL235221A (OSRAM) |
| LT (1) | LT2882715T (OSRAM) |
| MX (1) | MX347615B (OSRAM) |
| PL (1) | PL2882715T3 (OSRAM) |
| PT (1) | PT2882715T (OSRAM) |
| RU (1) | RU2645344C2 (OSRAM) |
| SG (1) | SG11201407210SA (OSRAM) |
| SI (1) | SI2882715T1 (OSRAM) |
| WO (1) | WO2013171317A1 (OSRAM) |
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| 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 |
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| 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
Also Published As
| Publication number | Publication date |
|---|---|
| JP2015517514A (ja) | 2015-06-22 |
| HRP20170098T1 (hr) | 2017-03-24 |
| SI2882715T1 (sl) | 2017-03-31 |
| HUE032890T2 (hu) | 2017-11-28 |
| AU2013261718B2 (en) | 2017-10-19 |
| SG11201407210SA (en) | 2014-12-30 |
| EP2882715A1 (en) | 2015-06-17 |
| RU2014151360A (ru) | 2016-07-10 |
| AU2013261718A1 (en) | 2014-12-18 |
| PL2882715T3 (pl) | 2017-04-28 |
| CN104302625A (zh) | 2015-01-21 |
| US20150141477A1 (en) | 2015-05-21 |
| BR112014028406A2 (pt) | 2017-06-27 |
| MX2014014011A (es) | 2015-02-12 |
| CY1118618T1 (el) | 2017-07-12 |
| PT2882715T (pt) | 2016-12-30 |
| DK2882715T3 (en) | 2017-02-13 |
| ES2612205T3 (es) | 2017-05-12 |
| RU2645344C2 (ru) | 2018-02-21 |
| MX347615B (es) | 2017-05-04 |
| CN104302625B (zh) | 2017-04-19 |
| JP6257596B2 (ja) | 2018-01-10 |
| LT2882715T (lt) | 2017-02-10 |
| IL235221A (en) | 2016-06-30 |
| EP2882715B1 (en) | 2016-11-09 |
| US9346762B2 (en) | 2016-05-24 |
| WO2013171317A1 (en) | 2013-11-21 |
| KR20150010973A (ko) | 2015-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20180509 |
|
| FZDE | Discontinued |
Effective date: 20201125 |