JPH11510805A - 2−オキサゾリジノン誘導体のワンポット合成 - Google Patents
2−オキサゾリジノン誘導体のワンポット合成Info
- Publication number
- JPH11510805A JPH11510805A JP9508227A JP50822797A JPH11510805A JP H11510805 A JPH11510805 A JP H11510805A JP 9508227 A JP9508227 A JP 9508227A JP 50822797 A JP50822797 A JP 50822797A JP H11510805 A JPH11510805 A JP H11510805A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- preparing
- methyl
- iii
- 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
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Physical Or Chemical Processes And Apparatus (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.式(I)の化合物を調製するためのプロセスであって、 ここで、 R1およびR2は各々独立して水素またはC1-4アルキルであるか、あるいはR1とR2と が結合してアゼチジン環を形成する;および AはC3-6シクロアルキル、C1-3アルキル-C3-6シクロアルキルまたはC2-アルキル である; 但し、R1およびR2が共にメチルである場合、AはC2-アルキルでない; 以下の工程を含むプロセス: a)炭酸ナトリウムまたは炭酸水素ナトリウムおよびn-ブチルクロロホルメー トを添加し反応させることにより、式(II)で表されるメチル4-ニトロ-(L)-フ ェニルアラニネートヒドロクロリドからカルバメートを形成し、 式(III)で表されるメチル(S)-N-ブトキシカルボニル-4-ニトロフェニルアラ ニネートを得る工程 b)式(III)の化合物を還元して、式(IV)で表されるメチル(S)-N-ブトキ シカルボニル-4-アミノフェニルアラニネートを得る工程 c)式(IV)の化合物中のメチルエステル基-CO2CH3を還元して、式(V)で 表される(S)-N-ブトキシカルボニル-4-アミノフェニルアラニノールを得る工程 d)式(V)の化合物を閉環し、式(VI)で表される(S)-4-(4-アミノベンジ ル)-2-オキサゾリジノンを得る工程 e)式(VI)の化合物のジアゾニウム塩を調製し、続いて還元し、式(VII) で表されるヒドラジン(S)-4-(4-ヒドラジノベンジル)-2-オキサゾリジノンヒド ロクロリドを得る工程 f)式(VII)の化合物のフィッシャー反応により式(I)の化合物を得る工 程。 2.Aがシクロブチルである、式(I)の化合物を調製するための、請求項1に 記載のプロセス。 3.4-[-3-(3-(トランス-3-ジメチルアミノシクロブチル)-1H-インドール-5-イ ルメチル]-(4S)オキサゾリジン-2-オンを調製するための請求項2に記載のプロ セス。 4.ワンポット手順を使用して工程a)からf)の1個以上の工程が実施される 、請求項1〜3のいずれかに記載のプロセス。 5.ワンポット手順によって工程a)からd)が実施され、続いて式(VI)の化 合物が単離され、そして工程e)およびf)が第二のワンポット手順で実施され る、請求項1〜3のいずれか1項に記載のプロセス。 6.式(III)の中間体 7.式(IV)の中間体 8.式(V)の中間体 9.式(VI)の中間体 10.式(III)の化合物を調製するプロセスであって、 式(II)の化合物を炭酸ナトリウムおよびn-ブチルクロロホルメートと反応させ る工程を包含するプロセス 11.式(IV)の化合物を調製するプロセスであって、 式(III)の化合物を還元する工程を包含するプロセス 12.式(V)の化合物を調製するプロセスであって、 式(IV)の化合物を還元する工程を包含するプロセス 13.式(VI)の化合物を調製するプロセスであって、 式(V)の化合物を閉環する工程を包含するプロセス 14.医薬使用のための組成物の製造における、請求項6に記載の中間体の使用 。 15.医薬使用のための組成物の製造における、請求項7に記載の中間体の使用 。 16.医薬使用のための組成物の製造における、請求項8に記載の中間体の使用 。 17.医薬使用のための組成物の製造における、請求項9に記載の中間体の使用 。 18.前記組成物が偏頭痛の治療および予防において使用される、請求項14〜 17のいずれか1項に記載の使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9516143.6A GB9516143D0 (en) | 1995-08-07 | 1995-08-07 | Improved chemical synthesis |
GB9516143.6 | 1995-08-07 | ||
PCT/GB1996/001886 WO1997006163A1 (en) | 1995-08-07 | 1996-08-02 | One pot synthesis of 2-oxazolidinone derivatives |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2002087016A Division JP2002308874A (ja) | 1995-08-07 | 2002-03-26 | 2−オキサゾリジノン誘導体のワンポット合成 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPH11510805A true JPH11510805A (ja) | 1999-09-21 |
JP3729504B2 JP3729504B2 (ja) | 2005-12-21 |
Family
ID=10778865
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP50822797A Expired - Lifetime JP3729504B2 (ja) | 1995-08-07 | 1996-08-02 | 2−オキサゾリジノン誘導体のワンポット合成 |
JP2002087016A Withdrawn JP2002308874A (ja) | 1995-08-07 | 2002-03-26 | 2−オキサゾリジノン誘導体のワンポット合成 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2002087016A Withdrawn JP2002308874A (ja) | 1995-08-07 | 2002-03-26 | 2−オキサゾリジノン誘導体のワンポット合成 |
Country Status (8)
Country | Link |
---|---|
US (1) | US6303791B1 (ja) |
EP (1) | EP0843673B1 (ja) |
JP (2) | JP3729504B2 (ja) |
AT (1) | ATE208388T1 (ja) |
AU (1) | AU6663596A (ja) |
DE (1) | DE69616801T2 (ja) |
GB (1) | GB9516143D0 (ja) |
WO (1) | WO1997006163A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1799675A4 (en) * | 2004-04-22 | 2010-04-28 | Reddys Lab Ltd Dr | PROCESS FOR THE PRODUCTION OF OPTICALLY PURE ZOLMITRIPTAN |
US20050245585A1 (en) * | 2004-04-22 | 2005-11-03 | Islam Aminul | Process for preparing optically pure zolmitriptan |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB8724912D0 (en) | 1987-10-23 | 1987-11-25 | Wellcome Found | Indole derivatives |
CA2064815C (en) | 1990-06-07 | 1999-11-16 | Alan Duncan Robertson | Therapeutic heterocyclic compounds |
GB9401436D0 (en) * | 1994-01-26 | 1994-03-23 | Wellcome Found | Therapeutic heterocyclic compounds |
-
1995
- 1995-08-07 GB GBGB9516143.6A patent/GB9516143D0/en active Pending
-
1996
- 1996-08-02 EP EP96926466A patent/EP0843673B1/en not_active Expired - Lifetime
- 1996-08-02 AT AT96926466T patent/ATE208388T1/de active
- 1996-08-02 US US09/011,044 patent/US6303791B1/en not_active Expired - Lifetime
- 1996-08-02 DE DE69616801T patent/DE69616801T2/de not_active Expired - Lifetime
- 1996-08-02 AU AU66635/96A patent/AU6663596A/en not_active Abandoned
- 1996-08-02 JP JP50822797A patent/JP3729504B2/ja not_active Expired - Lifetime
- 1996-08-02 WO PCT/GB1996/001886 patent/WO1997006163A1/en active IP Right Grant
-
2002
- 2002-03-26 JP JP2002087016A patent/JP2002308874A/ja not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
JP3729504B2 (ja) | 2005-12-21 |
GB9516143D0 (en) | 1995-10-04 |
DE69616801D1 (de) | 2001-12-13 |
ATE208388T1 (de) | 2001-11-15 |
EP0843673A1 (en) | 1998-05-27 |
JP2002308874A (ja) | 2002-10-23 |
EP0843673B1 (en) | 2001-11-07 |
AU6663596A (en) | 1997-03-05 |
WO1997006163A1 (en) | 1997-02-20 |
US6303791B1 (en) | 2001-10-16 |
DE69616801T2 (de) | 2002-06-06 |
Similar Documents
Publication | Publication Date | Title |
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JP4634286B2 (ja) | 2−オキサゾリジノン誘導体のワンポット合成 | |
WO2004067498A2 (fr) | Derives d’ arylalkylcarbamates, leur preparation et leur application en therapeutique | |
US20060264643A1 (en) | One Pot Synthesis of 2-Oxazolidinone Derivatives | |
JPH11510805A (ja) | 2−オキサゾリジノン誘導体のワンポット合成 | |
JP3163295B2 (ja) | イソオキサゾリジンジオン化合物の製造方法 | |
CH383972A (fr) | Procédé de préparation de phényloxyméthyl-2-oxazolidinones |
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