JP2003534332A5 - - Google Patents
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- Publication number
- JP2003534332A5 JP2003534332A5 JP2001586272A JP2001586272A JP2003534332A5 JP 2003534332 A5 JP2003534332 A5 JP 2003534332A5 JP 2001586272 A JP2001586272 A JP 2001586272A JP 2001586272 A JP2001586272 A JP 2001586272A JP 2003534332 A5 JP2003534332 A5 JP 2003534332A5
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- added
- dichlorobenzyl
- bis
- diazepan
- 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.)
- Granted
Links
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- -1 2-methoxy-naphthalen-1-ylmethyl Chemical group 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WYLQARGYFXBZMD-UHFFFAOYSA-N n-[chloro(dimethylamino)phosphoryl]-n-methylmethanamine Chemical compound CN(C)P(Cl)(=O)N(C)C WYLQARGYFXBZMD-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- WMRVYQNEOLTIMH-UHFFFAOYSA-N (2-methylnaphthalen-1-yl)methanamine Chemical compound C1=CC=CC2=C(CN)C(C)=CC=C21 WMRVYQNEOLTIMH-UHFFFAOYSA-N 0.000 description 1
- ZDEQBVQEYCMRPC-NRFANRHFSA-N (3s)-3-[(3,4-dichlorophenyl)methyl]-1-[(2-methoxynaphthalen-1-yl)methyl]-1,4-diazepane-2,5-dione Chemical compound C([C@@H]1NC(=O)CCN(C1=O)CC1=C2C=CC=CC2=CC=C1OC)C1=CC=C(Cl)C(Cl)=C1 ZDEQBVQEYCMRPC-NRFANRHFSA-N 0.000 description 1
- NQUZJPALTDPICI-QFIPXVFZSA-N (3s)-3-[(3,4-dichlorophenyl)methyl]-1-[(2-methylnaphthalen-1-yl)methyl]-1,4-diazepane-2,5-dione Chemical compound C([C@@H]1NC(=O)CCN(C1=O)CC1=C2C=CC=CC2=CC=C1C)C1=CC=C(Cl)C(Cl)=C1 NQUZJPALTDPICI-QFIPXVFZSA-N 0.000 description 1
- ISKGPEICYLVOOO-UHFFFAOYSA-N 1-[[3,5-bis(trifluoromethyl)phenyl]methyl]-3-[(3,4-dichlorophenyl)methyl]-5-sulfanylidene-1,4-diazepan-2-one Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(CN2C(C(CC=3C=C(Cl)C(Cl)=CC=3)NC(=S)CC2)=O)=C1 ISKGPEICYLVOOO-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00111249 | 2000-05-25 | ||
| EP00111249.9 | 2000-05-25 | ||
| PCT/EP2001/005723 WO2001090083A1 (en) | 2000-05-25 | 2001-05-18 | 1,4-diazepan-2,5-dione derivatives and their use as nk-1 receptor antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003534332A JP2003534332A (ja) | 2003-11-18 |
| JP2003534332A5 true JP2003534332A5 (enExample) | 2007-09-06 |
| JP4060596B2 JP4060596B2 (ja) | 2008-03-12 |
Family
ID=8168838
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001586272A Expired - Fee Related JP4060596B2 (ja) | 2000-05-25 | 2001-05-18 | １，４−ジアゼパン−２，５−ジオン誘導体、およびｎｋ−１受容体アンタゴニストとしてのその使用 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6452001B2 (enExample) |
| EP (1) | EP1296961B1 (enExample) |
| JP (1) | JP4060596B2 (enExample) |
| KR (1) | KR100526696B1 (enExample) |
| CN (1) | CN1178923C (enExample) |
| AR (1) | AR028607A1 (enExample) |
| AT (1) | ATE353881T1 (enExample) |
| AU (2) | AU2001281778B2 (enExample) |
| BR (1) | BR0111062A (enExample) |
| CA (1) | CA2409842C (enExample) |
| DE (1) | DE60126614T2 (enExample) |
| DK (1) | DK1296961T3 (enExample) |
| ES (1) | ES2280392T3 (enExample) |
| MX (1) | MXPA02011464A (enExample) |
| PE (1) | PE20011266A1 (enExample) |
| PT (1) | PT1296961E (enExample) |
| WO (1) | WO2001090083A1 (enExample) |
| ZA (1) | ZA200208940B (enExample) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2598762A1 (en) | 2005-02-25 | 2006-08-31 | F. Hoffmann-La Roche Ag | Tablets with improved drug substance dispersibility |
| DE602006016168D1 (de) * | 2005-12-29 | 2010-09-23 | Immupharma France Sa | 1,3,5-triazepin-dionen zur Behandlung von Malaria |
| US7777030B2 (en) | 2005-12-29 | 2010-08-17 | Centre National de la Recherge Scientifique (CNRS) | Compositions and methods for the treatment and prevention of disease |
| AU2006331357B2 (en) * | 2005-12-29 | 2012-05-17 | Immupharma France Sa | Compositions and methods for synthesizing novel heterocyclic therapeutics |
| JP2009522236A (ja) * | 2005-12-29 | 2009-06-11 | イミュファルマ・フランス・エスアー | マラリアまたはエイズの処置のためのアザ複素環化合物 |
| AU2006331355B2 (en) * | 2005-12-29 | 2011-09-29 | Immupharma France Sa | Compositions and methods for the inhibition of phospholipase A2 |
| WO2007139992A2 (en) * | 2006-05-26 | 2007-12-06 | Novartis Ag | ALDOSTERONE SYNTHASE AND/OR 11β-HYDROXYLASE INHIBITORS |
| US8093268B2 (en) | 2007-01-24 | 2012-01-10 | Glaxo Group Limited | Pharmaceutical compositions comprising 2-methoxy-5-(5-trifluoromethyl-tetrazol-1-yl-benzyl)-(2S-phenylpiperidin-3S-yl-) |
| KR101044833B1 (ko) * | 2010-02-10 | 2011-06-28 | (주)혜성나노텍 | 무차광 온실 보온커텐 종형 개폐장치 |
| CN103951624B (zh) * | 2010-08-26 | 2019-04-16 | 兴和株式会社 | 1,4-二氮杂环庚烷衍生物或其盐的制造方法 |
| CA2839385C (en) | 2011-06-24 | 2018-10-30 | Construction Research & Technology Gmbh | Cementitious composition and admixture |
| CN108358893A (zh) * | 2018-02-10 | 2018-08-03 | 安徽唯诗杨信息科技有限公司 | 一种一锅法合成四氢化苯并-[1,4]-二氮杂环庚烷衍生物的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4022765A (en) | 1975-01-06 | 1977-05-10 | E. R. Squibb & Sons, Inc. | Triazolo[4,3-d][1,4]benzodiazepine-6-ones |
| IL111960A (en) | 1993-12-17 | 1999-12-22 | Merck & Co Inc | Morpholines and thiomorpholines their preparation and pharmaceutical compositions containing them |
| IL112134A (en) | 1993-12-29 | 1999-12-22 | Merck Sharp & Dohme | Substituted morpholine derivatives their preparation and pharmaceutical compositions containing them |
| IL112778A0 (en) | 1994-03-04 | 1995-05-26 | Merck & Co Inc | Substituted heterocycles, their preparation and pharmaceutical compositions containing them |
| US5719156A (en) | 1995-05-02 | 1998-02-17 | Schering Corporation | Piperazino derivatives as neurokinin antagonists |
| US5972938A (en) | 1997-12-01 | 1999-10-26 | Merck & Co., Inc. | Method for treating or preventing psychoimmunological disorders |
-
2001
- 2001-05-14 US US09/854,885 patent/US6452001B2/en not_active Expired - Fee Related
- 2001-05-18 DK DK01960225T patent/DK1296961T3/da active
- 2001-05-18 AU AU2001281778A patent/AU2001281778B2/en not_active Ceased
- 2001-05-18 ES ES01960225T patent/ES2280392T3/es not_active Expired - Lifetime
- 2001-05-18 KR KR10-2002-7015837A patent/KR100526696B1/ko not_active Expired - Fee Related
- 2001-05-18 DE DE60126614T patent/DE60126614T2/de not_active Expired - Lifetime
- 2001-05-18 EP EP01960225A patent/EP1296961B1/en not_active Expired - Lifetime
- 2001-05-18 WO PCT/EP2001/005723 patent/WO2001090083A1/en not_active Ceased
- 2001-05-18 CN CNB018099335A patent/CN1178923C/zh not_active Expired - Fee Related
- 2001-05-18 AU AU8177801A patent/AU8177801A/xx active Pending
- 2001-05-18 BR BR0111062-4A patent/BR0111062A/pt not_active Application Discontinuation
- 2001-05-18 AT AT01960225T patent/ATE353881T1/de not_active IP Right Cessation
- 2001-05-18 MX MXPA02011464A patent/MXPA02011464A/es active IP Right Grant
- 2001-05-18 CA CA002409842A patent/CA2409842C/en not_active Expired - Fee Related
- 2001-05-18 JP JP2001586272A patent/JP4060596B2/ja not_active Expired - Fee Related
- 2001-05-18 PT PT01960225T patent/PT1296961E/pt unknown
- 2001-05-21 PE PE2001000458A patent/PE20011266A1/es not_active Application Discontinuation
- 2001-05-23 AR ARP010102436A patent/AR028607A1/es unknown
-
2002
- 2002-11-04 ZA ZA200208940A patent/ZA200208940B/en unknown
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