CA2854424A1 - Substituted pyrazolyl-based carboxamide and urea derivatives bearing a phenyl moiety substituted with an so2-containing group as vanilloid receptor ligands - Google Patents
Substituted pyrazolyl-based carboxamide and urea derivatives bearing a phenyl moiety substituted with an so2-containing group as vanilloid receptor ligands Download PDFInfo
- Publication number
- CA2854424A1 CA2854424A1 CA2854424A CA2854424A CA2854424A1 CA 2854424 A1 CA2854424 A1 CA 2854424A1 CA 2854424 A CA2854424 A CA 2854424A CA 2854424 A CA2854424 A CA 2854424A CA 2854424 A1 CA2854424 A1 CA 2854424A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- phenyl
- fluoro
- pyrazol
- methylsulfonyl
- 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
- 108010062740 TRPV Cation Channels Proteins 0.000 title abstract description 27
- 102000011040 TRPV Cation Channels Human genes 0.000 title abstract description 26
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title abstract description 5
- 239000003446 ligand Substances 0.000 title abstract description 4
- 125000003226 pyrazolyl group Chemical group 0.000 title abstract description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 title abstract description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 title abstract description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 185
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 239
- 229910052731 fluorine Inorganic materials 0.000 claims description 131
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 129
- 229910052739 hydrogen Inorganic materials 0.000 claims description 87
- 101100495923 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr2 gene Proteins 0.000 claims description 66
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 59
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 57
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 37
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 37
- 102100029613 Transient receptor potential cation channel subfamily V member 1 Human genes 0.000 claims description 36
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 claims description 32
- 229910052794 bromium Inorganic materials 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 24
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 23
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 22
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- OUEKLNJUMVZULZ-UHFFFAOYSA-N 2-[4-(2-aminoethoxy)-3-methoxyphenyl]-n-[3-(3,4-dimethylphenyl)propyl]acetamide;hydron;chloride Chemical compound Cl.C1=C(OCCN)C(OC)=CC(CC(=O)NCCCC=2C=C(C)C(C)=CC=2)=C1 OUEKLNJUMVZULZ-UHFFFAOYSA-N 0.000 claims description 5
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- ALMLDUKMBVXEMK-UHFFFAOYSA-N 1-[3-fluoro-4-(2-methylsulfonylethyl)phenyl]-3-[[2-(3-methylphenyl)-5-(trifluoromethyl)pyrazol-3-yl]methyl]urea Chemical compound CC1=CC=CC(N2C(=CC(=N2)C(F)(F)F)CNC(=O)NC=2C=C(F)C(CCS(C)(=O)=O)=CC=2)=C1 ALMLDUKMBVXEMK-UHFFFAOYSA-N 0.000 claims 1
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
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Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11008927 | 2011-11-09 | ||
| EP11008927.3 | 2011-11-09 | ||
| PCT/EP2012/072143 WO2013068464A1 (en) | 2011-11-09 | 2012-11-08 | Substituted pyrazolyl-based carboxamide and urea derivatives bearing a phenyl moiety substituted with an so2-containing group as vanilloid receptor ligands |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2854424A1 true CA2854424A1 (en) | 2013-05-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2854424A Abandoned CA2854424A1 (en) | 2011-11-09 | 2012-11-08 | Substituted pyrazolyl-based carboxamide and urea derivatives bearing a phenyl moiety substituted with an so2-containing group as vanilloid receptor ligands |
Country Status (13)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX377845B (es) | 2014-03-07 | 2025-03-11 | Biocryst Pharm Inc | Inhibidores de calicreína plasmática humana. |
| EP3224252B1 (en) * | 2014-11-24 | 2019-01-09 | Medifron Dbt Inc. | Substituted oxazole- and thiazole-based carboxamide and urea derivatives as vanilloid receptor ligands ii |
| CN114920697A (zh) * | 2022-05-16 | 2022-08-19 | 河南应用技术职业学院 | 杂环基取代的茚满丙酰胺类化合物及其应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2011011797A (es) | 2009-05-07 | 2011-11-29 | Gruenenthal Gmbh | Fenilureas y fenilamidas sustituidas como ligandos del receptor de vanilloides. |
| PT2427436E (pt) | 2009-05-07 | 2013-03-04 | Gruenenthal Gmbh | Derivados aromáticos substituídos de carboxamida e ureia como ligantes de receptor de vanilóide |
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2012
- 2012-11-08 EP EP12783220.2A patent/EP2776401A1/en not_active Withdrawn
- 2012-11-08 IN IN865KON2014 patent/IN2014KN00865A/en unknown
- 2012-11-08 AR ARP120104205A patent/AR088799A1/es unknown
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- 2012-11-08 CA CA2854424A patent/CA2854424A1/en not_active Abandoned
- 2012-11-08 JP JP2014540456A patent/JP2014532744A/ja not_active Withdrawn
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- 2012-11-08 HK HK15102581.4A patent/HK1202117A1/xx unknown
- 2012-11-08 MX MX2014005233A patent/MX2014005233A/es not_active Application Discontinuation
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|---|---|
| WO2013068464A1 (en) | 2013-05-16 |
| MX2014005233A (es) | 2014-08-22 |
| CN104066720A (zh) | 2014-09-24 |
| HK1202117A1 (en) | 2015-09-18 |
| AU2012334068A1 (en) | 2014-05-22 |
| EP2776401A1 (en) | 2014-09-17 |
| TW201326135A (zh) | 2013-07-01 |
| BR112014011108A2 (pt) | 2017-05-16 |
| IN2014KN00865A (enrdf_load_html_response) | 2015-10-02 |
| JP2014532744A (ja) | 2014-12-08 |
| KR20140091041A (ko) | 2014-07-18 |
| AR088799A1 (es) | 2014-07-10 |
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