CN101058564B - 芳基烷基氨基甲酸酯衍生物的生产及其在治疗中的用途 - Google Patents
芳基烷基氨基甲酸酯衍生物的生产及其在治疗中的用途 Download PDFInfo
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- CN101058564B CN101058564B CN2007100840856A CN200710084085A CN101058564B CN 101058564 B CN101058564 B CN 101058564B CN 2007100840856 A CN2007100840856 A CN 2007100840856A CN 200710084085 A CN200710084085 A CN 200710084085A CN 101058564 B CN101058564 B CN 101058564B
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- 238000002560 therapeutic procedure Methods 0.000 title abstract 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 125000004076 pyridyl group Chemical group 0.000 claims description 39
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
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- ATWVRXHCNJUKIP-UHFFFAOYSA-N C(C)(=O)OCC(OCC)NC.C(C)NC(O)=O Chemical compound C(C)(=O)OCC(OCC)NC.C(C)NC(O)=O ATWVRXHCNJUKIP-UHFFFAOYSA-N 0.000 description 11
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 10
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- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 description 8
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- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/12—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having 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
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- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
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- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
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- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
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- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0300704A FR2850377B1 (fr) | 2003-01-23 | 2003-01-23 | Derives d'arylalkylcarbamates, leur preparation et leur application en therapeutique |
| FR03/00704 | 2003-01-23 |
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| CNB2004800027704A Division CN100506788C (zh) | 2003-01-23 | 2004-01-22 | 芳基烷基氨基甲酸酯衍生物的生产及其在治疗中的用途 |
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| CN101058564B true CN101058564B (zh) | 2010-05-26 |
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| CNB2004800027704A Expired - Fee Related CN100506788C (zh) | 2003-01-23 | 2004-01-22 | 芳基烷基氨基甲酸酯衍生物的生产及其在治疗中的用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| FR2864080B1 (fr) * | 2003-12-23 | 2006-02-03 | Sanofi Synthelabo | Derives de 1-piperazine-et-1-homopiperazine-carboxylates, leur preparation et leur application en therapeutique |
| FR2865205B1 (fr) | 2004-01-16 | 2006-02-24 | Sanofi Synthelabo | Derives de type aryloxyalkylcarbamates, leur preparation et leur application en therapeutique |
| FR2866886B1 (fr) | 2004-02-26 | 2007-08-31 | Sanofi Synthelabo | Derives d'aryl-et d'heteroaryl-akylcarbamates, leur preparation et leur application en therapeutique |
| FR2866884B1 (fr) * | 2004-02-26 | 2007-08-31 | Sanofi Synthelabo | Derives d'aryl-et d'heteroaryl-piperidinecarboxylates, leur preparation et leur application en therapeutique |
| FR2866885B1 (fr) | 2004-02-26 | 2007-08-31 | Sanofi Synthelabo | Derives de piperidinylalkylcarbamates, leur prepation et leur application en therapeutique |
| DE102004039326A1 (de) * | 2004-08-12 | 2006-02-16 | Abbott Gmbh & Co. Kg | Neue medizinische Verwendungen und Verfahren |
| EP2937341B1 (en) | 2004-12-30 | 2017-07-05 | Janssen Pharmaceutica N.V. | 4-(benzyl)-piperazine-1-carboxylic acid phenylamide derivatives and related compounds as modulators of fatty acid amide hydrolase (faah) for the treatment of anxiety, pain and other conditions |
| US20070155707A1 (en) * | 2005-12-29 | 2007-07-05 | Kadmus Pharmaceuticals, Inc. | Ionizable inhibitors of fatty acid amide hydrolase |
| WO2008030752A2 (en) * | 2006-09-07 | 2008-03-13 | N.V. Organon | Methods for determining effective doses of fatty acid amide hydrolase inhibitors in vivo |
| WO2008042892A2 (en) * | 2006-10-02 | 2008-04-10 | N.V. Organon | Fatty acid amide hydrolase inhibitors for energy metabolism disorders |
| US20080119549A1 (en) * | 2006-11-20 | 2008-05-22 | N.V. Organon | Metabolically-stabilized inhibitors of fatty acid amide hydrolase |
| US8124605B2 (en) * | 2007-07-06 | 2012-02-28 | Kinex Pharmaceuticals, Llc | Compositions and methods for modulating a kinase cascade |
| TW200948805A (en) * | 2008-03-07 | 2009-12-01 | Sigma Tau Ind Farmaceuti | Enol carbamate derivatives as modulators of fatty acid amide hydrolase |
| CN101538245B (zh) * | 2008-03-18 | 2011-02-16 | 中国科学院上海药物研究所 | 一类哒嗪酮类化合物及其制备方法和制备药物的用途 |
| UA108233C2 (uk) | 2010-05-03 | 2015-04-10 | Модулятори активності гідролази амідів жирних кислот | |
| WO2012015704A2 (en) | 2010-07-28 | 2012-02-02 | The Regents Of The University Of California | Peripherally restricted faah inhibitors |
| CA2844812C (en) | 2011-08-19 | 2019-10-22 | Daniele Piomelli | Meta-substituted biphenyl peripherally restricted faah inhibitors |
| CA2883144C (en) | 2012-08-30 | 2023-01-17 | Kinex Pharmaceuticals, Llc | N-(3-fluorobenzyl)-2-(5-(4-morpholinophenyl)pyridin-2-yl) acetamide as protein|tyrosine kinase modulators |
| EP3988540A1 (en) | 2014-04-07 | 2022-04-27 | The Regents of the University of California | Inhibitors of fatty acid amide hydrolase (faah) enzyme with improved oral bioavailability and their use as medicaments |
| EA202191375A1 (ru) * | 2018-11-20 | 2021-09-21 | Байер Акциенгезельшафт | Антагонисты 2-адренорецепторов подтипа с (альфа-2с адренорецепторов) для лечения апноэ во сне |
| CN118515624B (zh) * | 2024-04-29 | 2025-01-24 | 聊城金歌合成材料有限公司 | 一种含三氟甲基多取代恶唑烷-4-酮的合成方法及应用 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2909467A (en) * | 1958-07-09 | 1959-10-20 | Us Vitamin Pharm Corp | 3-(d-alpha-methylphenethyl)-5-methyl-1, 3-oxazolidine-2, 4-dione |
| US3311655A (en) * | 1960-05-24 | 1967-03-28 | France Etat | Process for the preparation of urethanes |
| DE3003653A1 (de) * | 1980-02-01 | 1981-08-06 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von n-substituierten oxazolindionen-(2,4) |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3742022A (en) * | 1967-05-08 | 1973-06-26 | A Verbiscar | Carbamate esters of physiologically active ph enenthylamines |
| JP2616989B2 (ja) * | 1989-04-03 | 1997-06-04 | 株式会社トクヤマ | 2,4―オキサゾリジンジオン化合物 |
| CA2083891A1 (en) * | 1991-12-03 | 1993-06-04 | Angus Murray Macleod | Heterocyclic compounds, compositions containing them and their use in therapy |
| GB9210744D0 (en) * | 1992-05-20 | 1992-07-08 | Pfizer Ltd | Antiviral peptides |
| US6462054B1 (en) * | 2000-03-27 | 2002-10-08 | The Scripps Research Institute | Inhibitors of fatty acid amide hydrolase |
| JP2004532229A (ja) * | 2001-04-27 | 2004-10-21 | ブリストル−マイヤーズ スクイブ カンパニー | 脂肪酸アミド加水分解酵素阻害剤 |
| PL373970A1 (en) * | 2002-02-08 | 2005-09-19 | Bristol-Myers Squibb Company | (oxime)carbamoyl fatty acid amide hydrolase inhibitors |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2909467A (en) * | 1958-07-09 | 1959-10-20 | Us Vitamin Pharm Corp | 3-(d-alpha-methylphenethyl)-5-methyl-1, 3-oxazolidine-2, 4-dione |
| US3311655A (en) * | 1960-05-24 | 1967-03-28 | France Etat | Process for the preparation of urethanes |
| DE3003653A1 (de) * | 1980-02-01 | 1981-08-06 | Hoechst Ag, 6000 Frankfurt | Verfahren zur herstellung von n-substituierten oxazolindionen-(2,4) |
Non-Patent Citations (4)
| Title |
|---|
| Seymour L. Shapiro, Ira M. Rose, Frank C. Testa,等.N-Substituted Oxaolidiones.J. Of American Chemistry Society81 24.1959,81(24),6498-6504. * |
| Seymour L.Shapiro, Ira M. Rose, Frank C.Testa,等.N-Substituted Oxaolidiones.J.Of American Chemistry Society81 24.1959,81(24),6498-6504. * |
| Stefania Cesa, Vittoria Mucciante, Leucio Rossi.Tetraethyllmmonium Hydrogen Carbonate organicSynthisis:Synthesis of Oxaolidine-2,4-diones.Tetrahedron55 1.1999,55(1),193-200. * |
| Stefania Cesa,Vittoria Mucciante,Leucio Rossi.Tetraethyllmmonium Hydrogen Carbonate organicSynthisis:Synthesis of Oxaolidine-2,4-diones.Tetrahedron55 1.1999,55(1),193-200. * |
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