JP4454310B2 - 14ベータ−ヒドロキシ−バッカチンiii−1,14−カルボネートの調製方法 - Google Patents
14ベータ−ヒドロキシ−バッカチンiii−1,14−カルボネートの調製方法 Download PDFInfo
- Publication number
- JP4454310B2 JP4454310B2 JP2003538149A JP2003538149A JP4454310B2 JP 4454310 B2 JP4454310 B2 JP 4454310B2 JP 2003538149 A JP2003538149 A JP 2003538149A JP 2003538149 A JP2003538149 A JP 2003538149A JP 4454310 B2 JP4454310 B2 JP 4454310B2
- Authority
- JP
- Japan
- Prior art keywords
- baccatin iii
- iii
- keto
- hydroxy
- triethylsilyl
- 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.)
- Expired - Fee Related
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/08—Bridged systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
- C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Epoxy Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Description
a.下記式:
b.1及び14ヒドロキシルを炭酸化し、下記式:
c.13位のケトンを還元し、7位の保護基を開裂させる工程。
AcOEt=酢酸エチル;TES=トリエチルシリル;TESCl=塩化トリエチルシリル;DCM=ジクロロメタン;THF=テトラヒドロフラン。
a)13−ケト−バッカチンIII
バッカチンIII(150g、0.25mol)をアセトン(1.43l)に溶解した。強力な撹拌下で、市販の二酸化マンガン(450g)を3回に分けて加えた。出発物質が消失後(4時間)、この懸濁液を濾過して溶媒を留去した。粗生成物をAcOEt(100ml)に懸濁して、1時間還流し、次にc−ヘキサン(100ml)を加えた。溶媒の留去後、標題化合物を母液から、白色の固体(140g、95%)として得た。
13−ケト−バッカチンIII(5g、8.5mmol)、TESCl(3.6ml、21.4mmol、2.5当量)及びN−メチルイミダゾール(2.73ml、34.3mmol、4当量)を無水DCM(25ml)に溶解した。この溶液を撹拌下で1.5時間放置し、次に2M NaHSO4(25ml)中にゆっくり注ぎ入れることによってクエンチした。水層を洗浄し、DCM(2×10ml)で抽出して、合わせた有機層を食塩水(2×20ml)で抽出した。この有機溶液を硫酸ナトリウムで乾燥することにより、次の工程のために充分に純粋な標題化合物4.7gを得た。
7−TES−13−ケト−バッカチンIII(670mg、0.96mmol)を無水THF(9ml)とDMPU(2ml)との混合物に溶解して、N2下で−60℃に冷却した。前もって−50℃に冷却した、THF中のt−BuOKの1M溶液(2.5ml、0.86mmol)をここに滴下した。この溶液を−60℃で45分間撹拌し、次に無水THF(2ml)に溶解した(±)−ショウノウスルホニル−オキサジリジン(440mg、2mmol)を滴下により加えた。反応混合物を−60℃で3時間撹拌し、次に無水THF中の10% AcOH溶液(2ml)でクエンチした。次いでこの混合物が室温まで温まるのを待ち、次にDCM(2×10ml)で抽出した。合わせた有機層を水、NaCl飽和水溶液(15ml)で洗浄して、Na2SO4で乾燥した。フラッシュクロマトグラフィー(シリカゲル、cHex−AcOEt、8:2)により標題化合物を収率79%で精製した。あるいは、更に精製することなく、これを次の工程に直接使用した。
無水DCM(50ml)及びピリジン(16ml)中の14β−ヒドロキシ−7−TES−13−ケト−バッカチン(12.2g)の溶液を、DCM中の20%ホスゲン溶液(45mL、5当量)に−10℃で滴下した。2時間後、反応液に、5% NaHCO3水溶液(100ml)を滴下により加えた。水層をDCM(3×50ml)で洗浄して、粗生成物をフラッシュクロマトグラフィー(シリカゲル、DCM−AcOEt=50:1)により精製し、標題化合物を収率95%で得た。
無水エタノール(10ml)中のNaBH4(0.5g)の懸濁液を−50℃に冷却して、無水エタノール(10ml)中の14−ヒドロキシ−7−TES−13−ケト−バッカチンIII 1,14−β−カルボネート(0.5g、0.6mmol)の冷却溶液を加えた。出発物質が消失後(8時間)、クエン酸で反応をクエンチして、AcOEtで抽出した。合わせた有機層を硫酸ナトリウムで乾燥して、溶媒を留去した。クロマトグラフィー後、標題化合物を白色の固体として収率85%で得た。
14−ヒドロキシ−7−TES−バッカチンIII 1,14−β−カルボネート(9.6g、1.3mmol)を、アセトニトリル(5.4ml)とピリジン(6.4ml)との混合物に溶解して、0℃に冷却した。ピリジン(0.95ml)中の70% HF溶液を15分で滴下して、この溶液を室温で一晩撹拌した。次に反応混合物を氷20mL中に注ぎ入れ、撹拌下に1時間放置し、次にDCM(3×10ml)で抽出して、合わせた有機層を10% NaHSO4(pH=2まで)、5% NaHCO3(2×10ml)及び食塩水(2×10ml)で洗浄した。溶媒の留去後、標題化合物を白色の固体として収率96%で得た。
Claims (9)
- 工程a)が、−40〜−78℃の温度で、オキサジリジン誘導体の存在下、ヘキサメチルホスホルアミド(HMPA)又は1,3−ジメチル−3,4,5,6−テトラヒドロ−2(1H)ピリミジノン(DMPU)と混合したエーテル中で、カリウムt−ブトキシド又はカリウムビス(トリメチルシリル)アミドでの処理によって行われる、請求項1記載の方法。
- オキサジリジン誘導体が、N−ベンゼンスルホニルフェニルオキサジリジン、N−ベンゼンスルホニルm−ニトロフェニルオキサジリジン及びショウノウスルホニルオキサジリジンから選択される、請求項2記載の方法。
- 工程b)が、−40℃〜室温の範囲の温度で、塩基の存在下、塩素化溶媒中でのカルボニルジイミダゾール又はホスゲンによる処理によって行われる、請求項1〜3のいずれか1項記載の方法。
- 工程c)が、−20〜−50℃の温度で、水素化物による処理によって行われる、請求項1〜4のいずれか1項記載の方法。
- 水素化物が、水素化ホウ素ナトリウム、水素化ホウ素リチウム、トリアセトキシ水素化ホウ素ナトリウムから選択され、そして反応が、エタノール、メタノール、イソプロパノール、又はメタノールとテトラヒドロフランの混合物中で行われる、請求項5記載の方法。
- 7−トリエチルシリル−13−ケトバッカチンIIIが、10−デアセチルバッカチンIIIを、無水酢酸中CeCl 3 で処理することにより選択的にアセチル化してバッカチンIIIを得、アセトン中二酸化マンガンによりバッカチンIIIを酸化して、13−ケト−バッカチンIIIを得、次いで無水ジクロロメタン中塩化トリエチルシリル及びN−メチルイミダゾールで処理することにより13−ケト−バッカチンIIIの7位のヒドロキシル基をトリエチルシリルで保護することによって調製される、請求項1〜6のいずれか1項記載の方法。
- 13−ケト−バッカチンIIIが、無水酢酸によるデアセチルバッカチンIIIの10位での選択的アセチル化と、これに続く0℃〜60℃での非プロトン性溶媒中での二酸化マンガンによる酸化によって得られる、請求項7記載の方法。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT2001MI002186A ITMI20012186A1 (it) | 2001-10-19 | 2001-10-19 | Procedimento per la preparazione della 14-beta-idrossi-baccatina iii-1,14-carbonato |
PCT/EP2002/008005 WO2003035633A1 (en) | 2001-10-19 | 2002-07-18 | A process for the preparation of the 14beta-hydroxy-baccatin iii-1,14-carbonate |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2005512977A JP2005512977A (ja) | 2005-05-12 |
JP4454310B2 true JP4454310B2 (ja) | 2010-04-21 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003538149A Expired - Fee Related JP4454310B2 (ja) | 2001-10-19 | 2002-07-18 | 14ベータ−ヒドロキシ−バッカチンiii−1,14−カルボネートの調製方法 |
Country Status (20)
Country | Link |
---|---|
US (1) | US7078432B2 (ja) |
EP (1) | EP1436277B1 (ja) |
JP (1) | JP4454310B2 (ja) |
KR (1) | KR100896542B1 (ja) |
CN (1) | CN1271061C (ja) |
AT (1) | ATE537160T1 (ja) |
AU (1) | AU2002328918B2 (ja) |
BR (1) | BR0213360B1 (ja) |
CA (1) | CA2463915C (ja) |
DK (1) | DK1436277T3 (ja) |
ES (1) | ES2376162T3 (ja) |
HK (1) | HK1069170A1 (ja) |
HU (1) | HUP0401989A3 (ja) |
IL (1) | IL161443A0 (ja) |
IT (1) | ITMI20012186A1 (ja) |
MX (1) | MXPA04003519A (ja) |
NO (1) | NO328562B1 (ja) |
PL (1) | PL368122A1 (ja) |
RU (1) | RU2291866C2 (ja) |
WO (1) | WO2003035633A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010270145A (ja) * | 2002-09-10 | 2010-12-02 | Indena Spa | 14位で官能化されたタキサン誘導体及びその製造方法 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ITMI20012185A1 (it) * | 2001-10-19 | 2003-04-19 | Indena Spa | Procedimento per la preparazione della 14beta-idrossi-baccatina iii-1,14-carbonato |
EP2080764B1 (en) | 2008-01-18 | 2012-08-22 | INDENA S.p.A. | Solid forms of ortataxel |
CN103450118A (zh) * | 2013-09-18 | 2013-12-18 | 江苏红豆杉药业有限公司 | 一种半合成法制备紫杉醇的方法 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IT1254517B (it) | 1992-03-06 | 1995-09-25 | Indena Spa | 14-beta idrossi-10-deacetil-baccatina iii, suoi derivati, loro prepazione ed impiego terapeutico |
US5475011A (en) | 1993-03-26 | 1995-12-12 | The Research Foundation Of State University Of New York | Anti-tumor compounds, pharmaceutical compositions, methods for preparation thereof and for treatment |
IT1275936B1 (it) | 1995-03-17 | 1997-10-24 | Indena Spa | Derivati della 10-deacetilbaccatina iii e della 10-deacetil-14b- idrossibaccatina iii loro metodo di preparazione e formulazioni |
FR2732341A1 (fr) * | 1995-03-27 | 1996-10-04 | Rhone Poulenc Rorer Sa | Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent |
IT1275435B (it) * | 1995-05-19 | 1997-08-07 | Indena Spa | Derivati della 10-desacetil-14beta-idrossibaccatina iii,loro metodo di preparazione e formulazioni che li contengono |
IT1283633B1 (it) * | 1996-05-10 | 1998-04-23 | Indena Spa | Derivati tassanici loro sintesi e formulazioni che li contengono |
US5811452A (en) * | 1997-01-08 | 1998-09-22 | The Research Foundation Of State University Of New York | Taxoid reversal agents for drug-resistance in cancer chemotherapy and pharmaceutical compositions thereof |
IT1318678B1 (it) | 2000-08-10 | 2003-08-27 | Indena Spa | Procedimento per la preparazione di derivati della baccatina iii. |
IT1320107B1 (it) * | 2000-11-28 | 2003-11-18 | Indena Spa | Procedimento per la preparazione di derivati tassanici. |
ITMI20012185A1 (it) * | 2001-10-19 | 2003-04-19 | Indena Spa | Procedimento per la preparazione della 14beta-idrossi-baccatina iii-1,14-carbonato |
-
2001
- 2001-10-19 IT IT2001MI002186A patent/ITMI20012186A1/it unknown
-
2002
- 2002-07-18 AT AT02764721T patent/ATE537160T1/de active
- 2002-07-18 WO PCT/EP2002/008005 patent/WO2003035633A1/en active Application Filing
- 2002-07-18 DK DK02764721.3T patent/DK1436277T3/da active
- 2002-07-18 IL IL16144302A patent/IL161443A0/xx active IP Right Grant
- 2002-07-18 JP JP2003538149A patent/JP4454310B2/ja not_active Expired - Fee Related
- 2002-07-18 ES ES02764721T patent/ES2376162T3/es not_active Expired - Lifetime
- 2002-07-18 CA CA002463915A patent/CA2463915C/en not_active Expired - Lifetime
- 2002-07-18 AU AU2002328918A patent/AU2002328918B2/en not_active Ceased
- 2002-07-18 HU HU0401989A patent/HUP0401989A3/hu unknown
- 2002-07-18 PL PL02368122A patent/PL368122A1/xx not_active Application Discontinuation
- 2002-07-18 BR BRPI0213360-1B1A patent/BR0213360B1/pt not_active IP Right Cessation
- 2002-07-18 RU RU2004111669/04A patent/RU2291866C2/ru active
- 2002-07-18 US US10/492,986 patent/US7078432B2/en not_active Expired - Lifetime
- 2002-07-18 EP EP02764721A patent/EP1436277B1/en not_active Expired - Lifetime
- 2002-07-18 CN CNB028205227A patent/CN1271061C/zh not_active Expired - Fee Related
- 2002-07-18 MX MXPA04003519A patent/MXPA04003519A/es active IP Right Grant
- 2002-07-18 KR KR1020047004621A patent/KR100896542B1/ko active IP Right Grant
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2004
- 2004-04-15 NO NO20041537A patent/NO328562B1/no not_active IP Right Cessation
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2005
- 2005-02-28 HK HK05101660A patent/HK1069170A1/xx not_active IP Right Cessation
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010270145A (ja) * | 2002-09-10 | 2010-12-02 | Indena Spa | 14位で官能化されたタキサン誘導体及びその製造方法 |
Also Published As
Publication number | Publication date |
---|---|
PL368122A1 (en) | 2005-03-21 |
CN1271061C (zh) | 2006-08-23 |
EP1436277A1 (en) | 2004-07-14 |
ES2376162T3 (es) | 2012-03-09 |
WO2003035633A1 (en) | 2003-05-01 |
CA2463915C (en) | 2009-11-24 |
JP2005512977A (ja) | 2005-05-12 |
CN1571779A (zh) | 2005-01-26 |
ATE537160T1 (de) | 2011-12-15 |
DK1436277T3 (da) | 2012-01-23 |
RU2291866C2 (ru) | 2007-01-20 |
MXPA04003519A (es) | 2004-07-23 |
HK1069170A1 (en) | 2005-05-13 |
HUP0401989A3 (en) | 2007-05-29 |
US7078432B2 (en) | 2006-07-18 |
NO328562B1 (no) | 2010-03-22 |
AU2002328918B2 (en) | 2008-09-04 |
ITMI20012186A1 (it) | 2003-04-19 |
CA2463915A1 (en) | 2003-05-01 |
RU2004111669A (ru) | 2005-04-20 |
IL161443A0 (en) | 2004-09-27 |
NO20041537L (no) | 2004-04-15 |
KR100896542B1 (ko) | 2009-05-07 |
KR20040045023A (ko) | 2004-05-31 |
EP1436277B1 (en) | 2011-12-14 |
BR0213360B1 (pt) | 2014-04-15 |
US20040266859A1 (en) | 2004-12-30 |
HUP0401989A2 (hu) | 2005-01-28 |
BR0213360A (pt) | 2004-10-26 |
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