JP4667044B2 - 5−クロロ−n−({(5s)−2−オキソ−3−[4−(3−オキソ−4−モルホリニル)−フェニル]−1,3−オキサゾリジン−5−イル}−メチル)−2−チオフェンカルボキサミドの製造方法 - Google Patents
5−クロロ−n−({(5s)−2−オキソ−3−[4−(3−オキソ−4−モルホリニル)−フェニル]−1,3−オキサゾリジン−5−イル}−メチル)−2−チオフェンカルボキサミドの製造方法 Download PDFInfo
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- chlorothiophene
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- 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
- C07D413/12—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 chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—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
- C07D333/26—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 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- 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
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Description
例えば、グリシドール(VI)は、特に比較的大量のとき、重合しやすく、従って保存時に安定ではなく、さらに毒性で潜在的に発癌性である。化合物(II)の製造における光延反応は、技術的に高価かつ不便である。その理由の1つは、比較的大きいバッチでは容易にラセミ化が起こることである。もう1つの理由は、トリフェニルホスフィンオキシドおよびジイソプロピルアゾジカルボキシレートヒドラジドが化学量論量で廃棄物として生成されるので、原子の経済性(atom economy)が極度に満足のいかないものであることである。さらに、標的分子(I)のオキサゾリジノン環中の窒素原子が、フタルイミド保護形態で導入される。しかしながら、保護基としてのフタル酸基をさらなる合成過程において除去せねばならず、このことは、工程数とさらなる廃棄物の増加を意味する。
第1工程:
5−クロロチオフェン−2−カルボニルクロリド(IV)
5−クロロチオフェン−2−カルボン酸(市販されている)53.6gを、トルエン344gに懸濁し、80℃に加熱する。この温度で、塩化チオニル47.2gを20分間かけて滴下して添加し、次いで混合物を75ないし80℃で30分間撹拌し、次いで還流温度で2時間、ガスの放出が完了するまで撹拌する。冷却後、反応混合物を、30ないし35℃、40ないし48ミリバールの圧力で、約200mlの容積まで濃縮する。かくして得られた酸塩化物のトルエン溶液を、次の工程で直接反応させる。
N−((S)−2,3−ジヒドロキシ−プロピル)−5−クロロチオフェン−2−カルボキサミド(VIII)
炭酸水素ナトリウム461gおよび(2S)−3−アミノ−プロパン−1,2−ジオールヒドロクロリド(VII)(市販されている)350gを、最初に13ないし15℃で水2.1lに加え、2−メチルテトラヒドロフラン950mlと混合する。トルエン180ml中の5−クロロチオフェン−2−カルボニルクロリド(約93%)535.3gを、この混合物に、15ないし18℃で冷却しながら、2時間かけて滴下して添加する。後処理に、相を分離し、数工程で、全部でトルエン1.5lを用いて有機相を混合する。沈殿した生成物を、吸引濾過し、酢酸エチルで洗浄し、乾燥させる。
収量:593.8g;理論値の91.8%に相当
融点:114ないし114.5℃
N−((S)−3−ブロモ−2−ヒドロキシ−プロピル)−5−クロロチオフェン−2−カルボキサミド(IX)
臭化水素酸の33%酢酸溶液301.7mlを、氷酢酸250ml中のN−((S)−2,3−ジヒドロキシ−プロピル)−5−クロロチオフェン−2−カルボキサミド(VIII)100gの懸濁物に、21ないし26℃で、30分間かけて添加する。続いて、酢酸無水物40mlを添加し、反応混合物を60ないし65℃で3時間撹拌する。次いで、20ないし25℃で、メタノール960mlを30分間かけて添加する。反応混合物を還流下で2.5時間撹拌し、次いで20ないし25℃で終夜撹拌する。後処理に、溶媒を約95ミリバールの減圧下で留去する。残存している懸濁物を1−ブタノール50mlおよび水350mlと混合する。沈殿した生成物を、吸引濾過し、水で洗浄し、乾燥させる。
収量:89.8g;理論値の70.9%に対応する。
融点:120℃
N−{(R)−2−ヒドロキシ−3−[4−(3−オキソ−モルホリン−4−イル)−フェニルアミノ]−プロピル}−5−クロロ−チオフェン−2−カルボキサミド(X)
N−((S)−3−ブロモ−2−ヒドロキシ−プロピル)−5−クロロチオフェン−2−カルボキサミド(IX)55gおよび4−(4−アミノフェニル)−3−モルホリノン(III)29.4g(製造方法は、例えば、WO−A01/47919、55ないし57頁に記載されている)を、20ないし25℃で、トルエン500mlに懸濁し、コリジン18.5gおよびエタノール10mlと混合する。反応混合物を103ないし105℃に6時間加熱し、次いで、熱いまま1−ブタノール50mlと混合する。30℃に冷却後、沈殿した反応生成物を吸引濾過し、トルエンおよび水で洗浄し、乾燥させる。
収量:42.0g;理論値の61.8%に対応する。
融点:198.5℃
5−クロロ−N−({(5S)−2−オキソ−3−[4−(3−オキソ−4−モルホリニル)−フェニル]−1,3−オキサゾリジン−5−イル}−メチル)−2−チオフェンカルボキサミド(I)
N−{(R)−2−ヒドロキシ−3−[4−(3−オキソ−モルホリン−4−イル)−フェニルアミノ]−プロピル}−5−クロロチオフェン−2−カルボキサミド(X)25gを、20ないし25℃で、トルエン250mlに懸濁し、1−メチル−2−ピロリドン37.5mlおよびN,N−カルボニルジイミダゾール11.9gと混合する。反応混合物を80ないし83℃で20分間加熱し、続いて115℃に1時間加熱する。20℃に冷却後、沈殿した反応生成物を吸引濾過し、各回25mlの水で2回洗浄し、60℃、減圧下で乾燥させる。
収量:23.7g;理論値の91.5%に対応する。
融点:230℃
Claims (10)
- 式(I)の5−クロロ−N−({(5S)−2−オキソ−3−[4−(3−オキソ−4−モルホリニル)−フェニル]−1,3−オキサゾリジン−5−イル}−メチル)−2−チオフェンカルボキサミドの製造方法であって、
第1工程で、5−クロロチオフェン−2−カルボニルクロリド(IV)を5−クロロチオフェン−2−カルボン酸の塩素化により製造し、次いで、
第2工程で、(2S)−3−アミノプロパン−1,2−ジオールヒドロクロリド(VII)と反応させ、N−((S)−2,3−ジヒドロキシ−プロピル)−5−クロロチオフェン−2−カルボキサミド(VIII)を得、これを、次いで、
第3工程で、N−((S)−3−ブロモ−2−ヒドロキシ−プロピル)−5−クロロチオフェン−2−カルボキサミド(IX)に変換し、これを、次いで、
第4工程で、4−(4−アミノフェニル)−3−モルホリノン(III)と反応させることによりN−{(R)−2−ヒドロキシ−3−[4−(3−オキソ−モルホリン−4−イル)−フェニルアミノ]−プロピル}−5−クロロチオフェン−2−カルボキサミド(X)に変換し、これを、次いで、
第5工程で、ホスゲンまたはホスゲン均等物と反応させる、
ことを特徴とする方法。 - N−((S)−2,3−ジヒドロキシ−プロピル)−5−クロロチオフェン−2−カルボキサミド(VIII)からのN−((S)−3−ブロモ−2−ヒドロキシ−プロピル)−5−クロロチオフェン−2−カルボキサミド(IX)の製造方法。
- N−{(R)−2−ヒドロキシ−3−[4−(3−オキソ−モルホリン−4−イル)−フェニルアミノ]−プロピル}−5−クロロチオフェン−2−カルボキサミド(X)の製造方法であって、N−((S)−3−ブロモ−2−ヒドロキシ−プロピル)−5−クロロチオフェン−2−カルボキサミド(IX)を、4−(4−アミノフェニル)−3−モルホリノン(III)と反応させることを特徴とする方法。
- 式(I)の5−クロロ−N−({(5S)−2−オキソ−3−[4−(3−オキソ−4−モルホリニル)−フェニル]−1,3−オキサゾリジン−5−イル}−メチル)−2−チオフェンカルボキサミドの製造方法であって、N−((S)−3−ブロモ−2−ヒドロキシ−プロピル)−5−クロロチオフェン−2−カルボキサミド(IX)を4−(4−アミノフェニル)−3−モルホリノン(III)と反応させることによりN−{(R)−2−ヒドロキシ−3−[4−(3−オキソ−モルホリン−4−イル)−フェニルアミノ]−プロピル}−5−クロロチオフェン−2−カルボキサミド(X)を製造し、N−{(R)−2−ヒドロキシ−3−[4−(3−オキソ−モルホリン−4−イル)−フェニルアミノ]−プロピル}−5−クロロチオフェン−2−カルボキサミド(X)を、ホスゲンまたはホスゲン均等物と反応させることを特徴とする方法。
- ホスゲン均等物がN,N−カルボニルジイミダゾールであることを特徴とする、請求項4に記載の方法。
- 1.1ないし1.3当量のN,N−カルボニルジイミダゾールを使用することを特徴とする、請求項5に記載の方法。
- 反応を1−メチル−2−ピロリドンとトルエンの溶媒混合物中で行うことを特徴とする、請求項4ないし請求項6のいずれかに記載の方法。
- N−((S)−3−ブロモ−2−ヒドロキシ−プロピル)−5−クロロチオフェン−2−カルボキサミド(IX)を、N−((S)−2,3−ジヒドロキシ−プロピル)−5−クロロチオフェン−2−カルボキサミド(VIII)の変換により製造することを特徴とする、請求項4に記載の方法。
- N−((S)−2,3−ジヒドロキシ−プロピル)−5−クロロチオフェン−2−カルボキサミド(VIII)を、5−クロロチオフェン−2−カルボニルクロリド(IV)を(2S)−3−アミノプロパン−1,2−ジオールヒドロクロリド(VII)と反応させることにより製造することを特徴とする、請求項8に記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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DE10300111A DE10300111A1 (de) | 2003-01-07 | 2003-01-07 | Verfahren zur Herstellung von 5-Chlor-N-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidin-5-yl}-methyl)-2-thiophencarboxamid |
PCT/EP2003/014871 WO2004060887A1 (de) | 2003-01-07 | 2003-12-24 | Verfahren zur herstellung von 5-chlor-n-({5s)-2-oxo-3-[4-(3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidin-5-yl}-methyl)-2-thiophencarboxamid |
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JP2006513227A JP2006513227A (ja) | 2006-04-20 |
JP4667044B2 true JP4667044B2 (ja) | 2011-04-06 |
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JP2004564216A Expired - Fee Related JP4667044B2 (ja) | 2003-01-07 | 2003-12-24 | 5−クロロ−n−({(5s)−2−オキソ−3−[4−(3−オキソ−4−モルホリニル)−フェニル]−1,3−オキサゾリジン−5−イル}−メチル)−2−チオフェンカルボキサミドの製造方法 |
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US (2) | US20070149522A1 (ja) |
EP (1) | EP1583761B1 (ja) |
JP (1) | JP4667044B2 (ja) |
AU (1) | AU2003296728A1 (ja) |
CA (1) | CA2512504C (ja) |
DE (2) | DE10300111A1 (ja) |
ES (1) | ES2360097T3 (ja) |
WO (1) | WO2004060887A1 (ja) |
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- 2003-12-24 WO PCT/EP2003/014871 patent/WO2004060887A1/de active Application Filing
- 2003-12-24 DE DE50313496T patent/DE50313496D1/de not_active Expired - Lifetime
- 2003-12-24 ES ES03814467T patent/ES2360097T3/es not_active Expired - Lifetime
- 2003-12-24 AU AU2003296728A patent/AU2003296728A1/en not_active Abandoned
- 2003-12-24 CA CA2512504A patent/CA2512504C/en not_active Expired - Fee Related
- 2003-12-24 EP EP03814467A patent/EP1583761B1/de not_active Expired - Fee Related
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CA2512504C (en) | 2012-08-21 |
EP1583761A1 (de) | 2005-10-12 |
US8106192B2 (en) | 2012-01-31 |
WO2004060887A1 (de) | 2004-07-22 |
DE10300111A1 (de) | 2004-07-15 |
ES2360097T3 (es) | 2011-05-31 |
DE50313496D1 (de) | 2011-04-07 |
US20070149522A1 (en) | 2007-06-28 |
AU2003296728A1 (en) | 2004-07-29 |
JP2006513227A (ja) | 2006-04-20 |
US20100081807A1 (en) | 2010-04-01 |
EP1583761B1 (de) | 2011-02-23 |
CA2512504A1 (en) | 2004-07-22 |
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