JP2007515453A - セファロスポリン合成に使用するための中間体の生成プロセス - Google Patents
セファロスポリン合成に使用するための中間体の生成プロセス Download PDFInfo
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- JP2007515453A JP2007515453A JP2006546070A JP2006546070A JP2007515453A JP 2007515453 A JP2007515453 A JP 2007515453A JP 2006546070 A JP2006546070 A JP 2006546070A JP 2006546070 A JP2006546070 A JP 2006546070A JP 2007515453 A JP2007515453 A JP 2007515453A
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- Prior art keywords
- formula
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- acid addition
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- 0 *[N+](*)(*)CC(CSC1C2N)=C(C([O-])=O)N1C2=O Chemical compound *[N+](*)(*)CC(CSC1C2N)=C(C([O-])=O)N1C2=O 0.000 description 3
- RIWCPXPOSJYJGO-UHFFFAOYSA-O CN1C(C(O)=O)=C(C[N+]2(C)CCCC2)CSC1C(C=O)N Chemical compound CN1C(C(O)=O)=C(C[N+]2(C)CCCC2)CSC1C(C=O)N RIWCPXPOSJYJGO-UHFFFAOYSA-O 0.000 description 1
- IIVPIDBZUUAWTF-UHFFFAOYSA-N C[N+]1(CC(CSC2C3N)=C(C([O-])=O)N2C3=O)CCCC1 Chemical compound C[N+]1(CC(CSC2C3N)=C(C([O-])=O)N2C3=O)CCCC1 IIVPIDBZUUAWTF-UHFFFAOYSA-N 0.000 description 1
- TYNQWNIJFGNOGQ-UHFFFAOYSA-N NC(C1SCC(CI)=C(C(O)=O)N11)C1=O Chemical compound NC(C1SCC(CI)=C(C(O)=O)N11)C1=O TYNQWNIJFGNOGQ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
Abstract
(式中、R1、R2及びR3は、互いに独立に、アキリル(aklyl)、アルケニル、アリール、ヒドロキシ(C1−6)アルキル、カルバモイル−(C1−6)アルキル、アミノ−(C1−6)アルキル、アクラミノ(aclamino)−(C1−6)アルキルもしくはカルボキシ(C1−6)アルキルであるか、又は、R2及びR3は、隣接する窒素原子と一緒に、脂環式5員から8員複素環を形成し、R1は、アルキル、アルケニル又はアリールを表す。)の、セファロスポリン合成のための中間体の生成のための新規プロセスに関する。本発明によるプロセスは、好ましくない副産物、特に式(I)のΔ2−類似化合物の形成を大幅に減少させる点で注目に値する。
Description
a)式III
c)段階b)で得られるような、式IAの化合物の、酸付加塩及び/又は水和物の形態への任意の変換と、
d)式Vのセフェピムを得るための、段階b)から得られる式IAの化合物又は段階c)から得られるその酸付加塩及び/又は水和物の、7−アミノ基のアシル化と、
の反応段階を含む、
式Vのセフェピム又はその酸付加塩及び/又はその水和物の1つの生成のためのプロセスに関する。
1H−NMR(300MHz,D2O):δ(ppm)=2.14(m,4H,−N+CH2CH 2−);2.93(s,3H,CH 3N+−);3.41−3.60(m,5H,−N+CH 2CH2−,SCH 2);3.87(d,1H,J=16.9Hz,SCH 2);3.92,4.67(2d,2H,J=13.9Hz,−CH 2−N+−);4.78(d,1H,J=5.2Hz,H−7);5.13(d,j=5.2Hz,H−6)。M.p.:165℃(分解)。
Claims (11)
- 式
の化合物ならびに、式Iの化合物の、酸付加塩及び/又は水和物の生成のための、プロセスであって、
a)式
b)式Iの化合物を得るための、式
の反応段階を含む、前記プロセス。 - 段階a)及びb)が1つの反応容器中で同時に行われる、請求項1に記載のプロセス。
- R1、R2及びR3が、互いに独立に、アルキル、アルケニル、アリール又はヒドロキシ(C1−6)アルキルである、請求項1又は請求項2の一項に記載のプロセス。
- プロトン性溶媒が、(C1−4)−アルコール又はいくつかの(C1−4)−アルコールの混合物である、請求項1から請求項4の一項に記載のプロセス。
- アルコールが、メタノール、エタノール、イソプロパノール、n−プロパノール、2−メチル−プロパン−2−オール、グリコール、グリセロール、プロパンジオール又はブタンジオールである、請求項5に記載のプロセス。
- アルコールが、イソプロパノール又は1,2−ブタンジオールである、請求項4に記載のプロセス。
- 段階b)から得られる式Iの化合物が、酸付加塩及び/又は水和物の形態で得られるか、又は酸付加塩及び/又は水和物に変換される、請求項1から7の一項に記載のプロセス。
- 酸付加塩が、ヨウ化水素酸塩又は塩酸塩である、請求項8に記載のプロセス。
- 水和物が、一水和物である、請求項8から9の一項に記載のプロセス。
- 式
a)式
b)式
c)段階b)から得られた式IAの化合物の、酸付加塩及び/又は水和物の形態への任意の変換と、
d)式Vのセフェピムを得るための、段階b)から得られる式IAの化合物又は段階c)から得られるその酸付加塩及び/又は水和物の、7−アミノ基のアシル化と、
の反応段階を含む、前記プロセス。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT20762003 | 2003-12-23 | ||
PCT/EP2004/014646 WO2005063772A1 (en) | 2003-12-23 | 2004-12-22 | Process for production of intermediates for use in cefalosporin synthesis |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2007515453A true JP2007515453A (ja) | 2007-06-14 |
JP4616844B2 JP4616844B2 (ja) | 2011-01-19 |
Family
ID=34716003
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006546070A Expired - Fee Related JP4616844B2 (ja) | 2003-12-23 | 2004-12-22 | セファロスポリン合成に使用するための中間体の生成プロセス |
Country Status (9)
Country | Link |
---|---|
US (1) | US7592447B2 (ja) |
EP (1) | EP1699804B1 (ja) |
JP (1) | JP4616844B2 (ja) |
CN (1) | CN100543027C (ja) |
AT (1) | ATE385500T1 (ja) |
DE (1) | DE602004011685T2 (ja) |
ES (1) | ES2298850T3 (ja) |
SI (1) | SI1699804T1 (ja) |
WO (1) | WO2005063772A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1773845A1 (en) * | 2004-07-16 | 2007-04-18 | Hetero Drugs Limited | Process for preparing pure cephalosporine intermediates |
WO2006075244A2 (en) * | 2005-01-17 | 2006-07-20 | Orchid Chemicals & Pharmaceuticals Ltd | Improved process for the preparation of cephalosporin antibiotic intermediate |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57167992A (en) * | 1981-04-09 | 1982-10-16 | Yamanouchi Pharmaceut Co Ltd | Novel cephalosporin compound |
JPS58174387A (ja) * | 1982-03-04 | 1983-10-13 | Bristol Mayers Kenkyusho Kk | 化学化合物 |
JPS61126088A (ja) * | 1984-10-01 | 1986-06-13 | グラクソ・グル−プ・リミテツド | セフアロスポリン化合物 |
JPH06184161A (ja) * | 1992-07-24 | 1994-07-05 | Bristol Myers Squibb Co | セファロスポリン中間体の製造法 |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CA1213882A (en) * | 1982-03-04 | 1986-11-12 | Jun Okumura | Cephalosporins |
GB2165245B (en) | 1984-10-01 | 1988-05-25 | Glaxo Group Ltd | Chemical compounds |
FR2585705B1 (fr) | 1985-08-05 | 1989-01-13 | Bristol Myers Co | Sels de cephalosporine et compositions injectables |
JPH06234768A (ja) | 1993-02-12 | 1994-08-23 | Sumitomo Electric Ind Ltd | 有機電荷移動錯体 |
EP1773845A1 (en) * | 2004-07-16 | 2007-04-18 | Hetero Drugs Limited | Process for preparing pure cephalosporine intermediates |
-
2004
- 2004-12-22 JP JP2006546070A patent/JP4616844B2/ja not_active Expired - Fee Related
- 2004-12-22 EP EP04804240A patent/EP1699804B1/en not_active Not-in-force
- 2004-12-22 CN CNB2004800384576A patent/CN100543027C/zh not_active Expired - Fee Related
- 2004-12-22 WO PCT/EP2004/014646 patent/WO2005063772A1/en active IP Right Grant
- 2004-12-22 DE DE602004011685T patent/DE602004011685T2/de active Active
- 2004-12-22 AT AT04804240T patent/ATE385500T1/de active
- 2004-12-22 ES ES04804240T patent/ES2298850T3/es active Active
- 2004-12-22 SI SI200430698T patent/SI1699804T1/sl unknown
- 2004-12-22 US US10/583,159 patent/US7592447B2/en not_active Expired - Fee Related
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS57167992A (en) * | 1981-04-09 | 1982-10-16 | Yamanouchi Pharmaceut Co Ltd | Novel cephalosporin compound |
JPS58174387A (ja) * | 1982-03-04 | 1983-10-13 | Bristol Mayers Kenkyusho Kk | 化学化合物 |
JPS61126088A (ja) * | 1984-10-01 | 1986-06-13 | グラクソ・グル−プ・リミテツド | セフアロスポリン化合物 |
JPH06184161A (ja) * | 1992-07-24 | 1994-07-05 | Bristol Myers Squibb Co | セファロスポリン中間体の製造法 |
Non-Patent Citations (2)
Title |
---|
JPN7010001444, DONALD G. WALKER ET AL, "Use of bistrimethylsilylated intermediates in the preparation of semisynthetic 7−amino−3−substituted", JOURNAL OF ORGANIC CHEMISTRY, 1988, vol.53, no.5, p.983−991 * |
JPN7010001445, YONG SUP LEE ET AL, "Synthesis and structure−activity relationships of quaternary ammonium cephalosporins with hydroxylat", JOURNAL OF ANTIBIOTICS, 199405, vol.47, no.5, p.609−612 * |
Also Published As
Publication number | Publication date |
---|---|
ES2298850T3 (es) | 2008-05-16 |
JP4616844B2 (ja) | 2011-01-19 |
CN100543027C (zh) | 2009-09-23 |
US20070191601A1 (en) | 2007-08-16 |
SI1699804T1 (sl) | 2008-08-31 |
WO2005063772A1 (en) | 2005-07-14 |
EP1699804B1 (en) | 2008-02-06 |
US7592447B2 (en) | 2009-09-22 |
ATE385500T1 (de) | 2008-02-15 |
CN1898250A (zh) | 2007-01-17 |
DE602004011685D1 (de) | 2008-03-20 |
DE602004011685T2 (de) | 2009-02-05 |
EP1699804A1 (en) | 2006-09-13 |
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