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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- GBWMNNAQBJOFKZ-UHFFFAOYSA-N methyl 2-(3-chloro-4-methylsulfanylphenyl)propanoate Chemical compound COC(=O)C(C)C1=CC=C(SC)C(Cl)=C1 GBWMNNAQBJOFKZ-UHFFFAOYSA-N 0.000 description 1
- YXFLRZABARLOGQ-UHFFFAOYSA-N methyl 2-(3-fluoro-4-methylsulfanylphenyl)propanoate Chemical compound COC(=O)C(C)C1=CC=C(SC)C(F)=C1 YXFLRZABARLOGQ-UHFFFAOYSA-N 0.000 description 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
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
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- Biomedical Technology (AREA)
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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
ID=47143914
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)
| Country | Link |
|---|---|
| EP (1) | EP2776401A1 (OSRAM) |
| JP (1) | JP2014532744A (OSRAM) |
| KR (1) | KR20140091041A (OSRAM) |
| CN (1) | CN104066720A (OSRAM) |
| AR (1) | AR088799A1 (OSRAM) |
| AU (1) | AU2012334068A1 (OSRAM) |
| BR (1) | BR112014011108A2 (OSRAM) |
| CA (1) | CA2854424A1 (OSRAM) |
| HK (1) | HK1202117A1 (OSRAM) |
| IN (1) | IN2014KN00865A (OSRAM) |
| MX (1) | MX2014005233A (OSRAM) |
| TW (1) | TW201326135A (OSRAM) |
| WO (1) | WO2013068464A1 (OSRAM) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| LT3113772T (lt) | 2014-03-07 | 2020-12-28 | Biocryst Pharmaceuticals, Inc. | Trifluormetilo pakeistieji pirazolai kaip žmogaus plazmos kalikreino inhibitoriai |
| CN107108593B (zh) * | 2014-11-24 | 2020-03-24 | 美迪福伦Dbt有限公司 | 作为类香草素受体配体ii的基于取代的恶唑和噻唑的羧酰胺和脲衍生物 |
| 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 |
|---|---|---|---|---|
| CA2758289A1 (en) | 2009-05-07 | 2010-11-11 | Gruenenthal Gmbh | Substituted aromatic carboxamide and urea derivatives as vanilloid receptor ligands |
| JP5745505B2 (ja) | 2009-05-07 | 2015-07-08 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | バニロイド受容体リガンドとしての置換フェニル尿素および置換フェニルアミド |
-
2012
- 2012-11-08 EP EP12783220.2A patent/EP2776401A1/en not_active Withdrawn
- 2012-11-08 CA CA2854424A patent/CA2854424A1/en not_active Abandoned
- 2012-11-08 IN IN865KON2014 patent/IN2014KN00865A/en unknown
- 2012-11-08 AR ARP120104205A patent/AR088799A1/es unknown
- 2012-11-08 AU AU2012334068A patent/AU2012334068A1/en not_active Abandoned
- 2012-11-08 JP JP2014540456A patent/JP2014532744A/ja not_active Withdrawn
- 2012-11-08 MX MX2014005233A patent/MX2014005233A/es not_active Application Discontinuation
- 2012-11-08 BR BR112014011108A patent/BR112014011108A2/pt not_active IP Right Cessation
- 2012-11-08 TW TW101141483A patent/TW201326135A/zh unknown
- 2012-11-08 WO PCT/EP2012/072143 patent/WO2013068464A1/en not_active Ceased
- 2012-11-08 KR KR1020147015421A patent/KR20140091041A/ko not_active Withdrawn
- 2012-11-08 HK HK15102581.4A patent/HK1202117A1/xx unknown
- 2012-11-08 CN CN201280055221.8A patent/CN104066720A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| HK1202117A1 (en) | 2015-09-18 |
| JP2014532744A (ja) | 2014-12-08 |
| CN104066720A (zh) | 2014-09-24 |
| BR112014011108A2 (pt) | 2017-05-16 |
| AR088799A1 (es) | 2014-07-10 |
| MX2014005233A (es) | 2014-08-22 |
| IN2014KN00865A (OSRAM) | 2015-10-02 |
| EP2776401A1 (en) | 2014-09-17 |
| AU2012334068A1 (en) | 2014-05-22 |
| TW201326135A (zh) | 2013-07-01 |
| KR20140091041A (ko) | 2014-07-18 |
| WO2013068464A1 (en) | 2013-05-16 |
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