CA2502705A1 - Aryl ureido derivatives and their medical use - Google Patents
Aryl ureido derivatives and their medical use Download PDFInfo
- Publication number
- CA2502705A1 CA2502705A1 CA002502705A CA2502705A CA2502705A1 CA 2502705 A1 CA2502705 A1 CA 2502705A1 CA 002502705 A CA002502705 A CA 002502705A CA 2502705 A CA2502705 A CA 2502705A CA 2502705 A1 CA2502705 A1 CA 2502705A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- cycloalkyl
- halo
- phenyl
- ureido
- 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
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- 150000001875 compounds Chemical class 0.000 claims abstract description 77
- 238000000034 method Methods 0.000 claims abstract description 54
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- 208000035475 disorder Diseases 0.000 claims abstract description 23
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- 102000018899 Glutamate Receptors Human genes 0.000 claims abstract description 9
- 230000001057 ionotropic effect Effects 0.000 claims abstract description 9
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims abstract description 8
- 229940009098 aspartate Drugs 0.000 claims abstract description 8
- 108010009117 Gluk1 kainate receptor Proteins 0.000 claims abstract 2
- 239000001257 hydrogen Substances 0.000 claims description 141
- 229910052739 hydrogen Inorganic materials 0.000 claims description 141
- 125000000217 alkyl group Chemical group 0.000 claims description 124
- 125000001188 haloalkyl group Chemical group 0.000 claims description 90
- 150000002431 hydrogen Chemical class 0.000 claims description 85
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 84
- 125000003545 alkoxy group Chemical group 0.000 claims description 59
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 56
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 125000000623 heterocyclic group Chemical group 0.000 claims description 36
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 34
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- 125000003342 alkenyl group Chemical group 0.000 claims description 32
- 125000000304 alkynyl group Chemical group 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 32
- 125000004043 oxo group Chemical group O=* 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
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- UAJJKABSBNCYAN-UHFFFAOYSA-N 4-chloro-5-methyl-2-(naphthalen-2-ylcarbamoylamino)benzenesulfonic acid Chemical compound C1=C(Cl)C(C)=CC(S(O)(=O)=O)=C1NC(=O)NC1=CC=C(C=CC=C2)C2=C1 UAJJKABSBNCYAN-UHFFFAOYSA-N 0.000 claims description 4
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- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- VSZKUIZXGWUDLH-UHFFFAOYSA-N 4-chloro-2-[(2-methoxyphenyl)carbamoylamino]benzoic acid Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC(Cl)=CC=C1C(O)=O VSZKUIZXGWUDLH-UHFFFAOYSA-N 0.000 claims description 3
- YJLYKRYWHIFVSR-UHFFFAOYSA-N 6-chloro-n-naphthalen-2-yl-3-oxo-2h-indazole-1-carboxamide Chemical compound C12=CC(Cl)=CC=C2C(O)=NN1C(=O)NC1=CC=C(C=CC=C2)C2=C1 YJLYKRYWHIFVSR-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/75—Amino or imino radicals, acylated by carboxylic or carbonic acids, or by sulfur or nitrogen analogues thereof, e.g. carbamates
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| ES2360818T3 (es) | 2005-06-27 | 2011-06-09 | Bristol-Myers Squibb Company | Miméticos de urea lineal antagonistas del receptor p2y, útiles en el tratamiento de afecciones trombóticas. |
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| MX2007016501A (es) | 2005-06-27 | 2008-03-06 | Squibb Bristol Myers Co | Antagonistas heterociclicos n-enlazados del receptor de p2y1, utiles en el tratamiento de condiciones tromboticas. |
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| AU2008309003A1 (en) * | 2007-09-28 | 2009-04-09 | Glaxosmithkline Llc | Glycogen phosphorylase inhibitor compound and pharmaceutical composition thereof |
| US20100292283A1 (en) * | 2007-11-28 | 2010-11-18 | Antonio Nardi | Novel phenyl-acetamide and phenyl-propionamide derivatives useful as potassium channel modulators |
| WO2011053468A1 (en) * | 2009-10-30 | 2011-05-05 | Sanofi-Aventis | Amino-benzoic acid derivatives for use in the treatment of dihydrogenase-related disorders |
| US10899702B2 (en) * | 2015-02-07 | 2021-01-26 | University of Pittsburgh—of the Commonwealth System of Higher Education | HTRPVI chemical agents |
| JP7092356B2 (ja) * | 2016-06-22 | 2022-06-28 | フーダン ユニヴァーシティ | ビアリール尿素誘導体またはそれらの塩、およびそれらの調製方法および使用 |
| CN106008371A (zh) * | 2016-06-24 | 2016-10-12 | 谢阳 | 1-芳基脲基环烷基-1-甲酰胺类化合物及其药物组合物和应用 |
| CN106946786A (zh) * | 2017-04-11 | 2017-07-14 | 白银澐新生物科技有限公司 | 一种1‑苄基‑3‑羟基‑1h‑3‑吲唑钠盐的制备方法 |
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| US7211575B2 (en) | 2001-09-13 | 2007-05-01 | Boehringer Ingelheim Pharmaceuticals, Inc. | Methods of treating cytokine mediated diseases |
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| WO2004046090A2 (en) | 2004-06-03 |
| US7521480B2 (en) | 2009-04-21 |
| ATE431335T1 (de) | 2009-05-15 |
| JP2006507329A (ja) | 2006-03-02 |
| DE60327652D1 (de) | 2009-06-25 |
| MXPA05005409A (es) | 2005-08-03 |
| ES2327834T3 (es) | 2009-11-04 |
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