CA2561639A1 - Novel urea derivatives and their medical use - Google Patents
Novel urea derivatives and their medical use Download PDFInfo
- Publication number
- CA2561639A1 CA2561639A1 CA002561639A CA2561639A CA2561639A1 CA 2561639 A1 CA2561639 A1 CA 2561639A1 CA 002561639 A CA002561639 A CA 002561639A CA 2561639 A CA2561639 A CA 2561639A CA 2561639 A1 CA2561639 A1 CA 2561639A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- hydroxy
- represents hydrogen
- halo
- alkyl
- 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
- 150000003672 ureas Chemical class 0.000 title claims abstract description 64
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 85
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- 239000001257 hydrogen Substances 0.000 claims description 205
- 229910052739 hydrogen Inorganic materials 0.000 claims description 205
- 150000002431 hydrogen Chemical class 0.000 claims description 140
- 125000005843 halogen group Chemical group 0.000 claims description 100
- 125000000217 alkyl group Chemical group 0.000 claims description 66
- 125000001188 haloalkyl group Chemical group 0.000 claims description 61
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 57
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 53
- -1 vitro Chemical group 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 49
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 45
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 41
- 125000003545 alkoxy group Chemical group 0.000 claims description 33
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 28
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 125000003342 alkenyl group Chemical group 0.000 claims description 19
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 9
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- OUDXRNQPVSMGDW-UHFFFAOYSA-N 1-(5-chloro-2-hydroxyphenyl)-3-[2-chloro-5-(trifluoromethyl)phenyl]urea Chemical compound OC1=CC=C(Cl)C=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1Cl OUDXRNQPVSMGDW-UHFFFAOYSA-N 0.000 claims description 3
- HGTNAHXLPRRYOU-UHFFFAOYSA-N 1-(5-chloro-2-methoxyphenyl)-3-[2-chloro-5-(trifluoromethyl)phenyl]urea Chemical compound COC1=CC=C(Cl)C=C1NC(=O)NC1=CC(C(F)(F)F)=CC=C1Cl HGTNAHXLPRRYOU-UHFFFAOYSA-N 0.000 claims description 3
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- C07C275/34—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by singly-bound oxygen atoms having nitrogen atoms of urea groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
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- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
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| DKPA200400498 | 2004-03-29 | ||
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| US55769804P | 2004-03-31 | 2004-03-31 | |
| US60/557,698 | 2004-03-31 | ||
| PCT/EP2005/051183 WO2005092843A1 (en) | 2004-03-29 | 2005-03-16 | Novel urea derivatives and their medical use |
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| WO2006089871A2 (en) * | 2005-02-23 | 2006-08-31 | Neurosearch A/S | Diphenylurea derivatives useful as erg channel openers for the treatment of cardiac arrhythmias |
| EP2255848A3 (en) * | 2006-09-04 | 2011-04-06 | NeuroSearch AS | Pharmaceutical combinations of a nicotine receptor modulator and a cognitive enhancer |
| WO2010130063A1 (zh) * | 2009-05-12 | 2010-11-18 | Han Mei | 具有促进干細胞增殖作用的小分子化合物及其用途 |
| WO2012029994A1 (en) | 2010-09-02 | 2012-03-08 | Kyoto University | Pharmaceutical composition for prevention and treatment of amyotrophic lateral sclerosis |
| US20130310419A1 (en) | 2011-02-03 | 2013-11-21 | Lupin Limited | Pyrrole derivatives used as modulators of alpha7 nachr |
| AU2012221800B2 (en) | 2011-02-23 | 2016-10-27 | Lupin Limited | Heteroaryl derivatives as alpha7 nAChR modulators |
| KR20140025395A (ko) | 2011-03-31 | 2014-03-04 | 루핀 리미티드 | 알츠하이머병 및 파킨슨병을 포함하는 신경병성 장애 치료용 니코틴성 아세틸콜린 수용체 조절인자로서의 피롤 유도체 |
| KR20140027939A (ko) | 2011-06-30 | 2014-03-07 | 도레이 카부시키가이샤 | 지양제 |
| EP2729455B1 (en) | 2011-07-05 | 2016-09-14 | Lupin Limited | Biaryl derivatives as nachr modulators |
| US8541577B2 (en) * | 2011-11-10 | 2013-09-24 | Allergan, Inc. | Aryl urea derivatives as N-formyl peptide receptors like-1 (FPRL-1) receptor modulators |
| CN103172543B (zh) * | 2011-12-21 | 2016-02-10 | 中国科学院上海药物研究所 | 一种脲类化合物、制备方法及其用途 |
| EP2822946A1 (en) | 2012-03-06 | 2015-01-14 | Lupin Limited | Thiazole derivatives as alpha 7 nachr modulators |
| EP2945936A1 (en) | 2012-11-12 | 2015-11-25 | Lupin Limited | Thiazole derivatives as alpha 7 nachr modulators |
| US9617211B2 (en) | 2013-01-16 | 2017-04-11 | Lupin Limited | Pyrrole derivatives as alpha 7 nAChR modulators |
| CA2892682A1 (en) | 2013-03-13 | 2014-09-18 | Lupin Limited | Pyrrole derivatives as alpha 7 nachr modulators |
| TW201446243A (zh) | 2013-06-03 | 2014-12-16 | Lupin Ltd | 4-(5-(4-氯苯基)-2-(2-環丙基乙醯基)-1,4-二甲基-1氫-吡咯-3-基)苯磺醯胺作為α7尼古丁乙醯膽鹼受體調節劑 |
| CA2913987A1 (en) | 2013-06-17 | 2014-12-24 | Lupin Limited | Pyrrole derivatives as alpha 7 nachr modulators |
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| DE3237479A1 (de) * | 1982-10-09 | 1984-04-12 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von substituierten tetrahydropyrimidinonderivaten |
| DK41193D0 (da) * | 1993-04-07 | 1993-04-07 | Neurosearch As | Ionkanalaabnere |
| ES2204920T3 (es) * | 1993-05-27 | 2004-05-01 | Cenes Limited | Guanidinas substituidas terapeuticas. |
| EP0809492A4 (en) * | 1995-02-17 | 2007-01-24 | Smithkline Beecham Corp | IL-8 RECEPTOR ANTAGONISTS |
| AU2962297A (en) * | 1996-05-24 | 1998-01-05 | Neurosearch A/S | Phenyl derivatives useful as blockers of chloride channels |
| EP1042305B1 (en) * | 1997-12-22 | 2005-06-08 | Bayer Pharmaceuticals Corp. | INHIBITION OF p38 KINASE USING SYMMETRICAL AND UNSYMMETRICAL DIPHENYL UREAS |
| ATE470195T1 (de) * | 1998-07-01 | 2010-06-15 | Univ Pennsylvania | Hohlraum-induzierte allosterische modifikation von intermolekularen interaktionen und verfahren zur identifikation von verbindungen, die diese bewirken. |
| JP2004523543A (ja) * | 2001-02-15 | 2004-08-05 | ニューロサーチ、アクティーゼルスカブ | 神経栄養活性を有する化合物とドパミン活性を増加させる化合物の組み合わせ作用によるパーキンソン病の治療法 |
| US20030236287A1 (en) | 2002-05-03 | 2003-12-25 | Piotrowski David W. | Positive allosteric modulators of the nicotinic acetylcholine receptor |
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| AU2005225559A1 (en) | 2005-10-06 |
| BRPI0507296A (pt) | 2007-07-03 |
| RU2006131454A (ru) | 2008-05-10 |
| CN1926098A (zh) | 2007-03-07 |
| US20070142450A1 (en) | 2007-06-21 |
| JP2007530635A (ja) | 2007-11-01 |
| WO2005092843A1 (en) | 2005-10-06 |
| EP1732883A1 (en) | 2006-12-20 |
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