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1. 发明授权

US6107497A Intermediate for use in docetaxel synthesis and production method therefor 失效
标题翻译：用于多西紫杉醇合成的中间体及其制备方法
公开(公告)号：US6107497A
公开(公告)日：2000-08-22
申请号：US616466
申请日：1996-03-19
申请人： Nicholas J. Sisti , Charles S. Swindell , Madhavi C. Chander
发明人： Nicholas J. Sisti , Charles S. Swindell , Madhavi C. Chander
IPC分类号： C07D305/14
CPC分类号： C07D305/14 , Y02P20/55
摘要： C7, C10 di-CBZ 10-deacetyl baccatin III of the formula: ##STR1## provides an intermediate for the production of docetaxel. A method of producing this C7, C10 di-CBZ 10-deacetyl Baccatin III is provided. Here, 10-deacetyl Baccatin III is acylated with at least 1.5 equivalents of n-butyl lithium and at least 1.5 equivalents of benzyl chloroformate in tetrahydrofuran. The 10-deacetyl Baccatin III may first be dissolved in tetrahydrofuran after which the n-butyl lithium is added followed by the addition of the benzyl chloroformate. The reaction is preferably at a reduced temperature of less than -20.degree. C. The resulting solution may be quenched with ammonium chloride and reduced to residue. The residue may then be redissolved in an organic solvent, washed, dried and recrystallized to purify the compound.
摘要翻译： C7，C10二-CZZ 10-脱乙酰浆果赤霉素III：提供用于制备多西紫杉醇的中间体。提供了制备该C7，C10二-CBZ10-脱乙酰芽胞素III的方法。这里，使用至少1.5当量的正丁基锂和至少1.5当量的氯甲酸苄酯在四氢呋喃中酰化10-deacetyl Baccatin III。可以将10-deacetyl Baccatin III溶于四氢呋喃中，然后加入正丁基锂，然后加入氯甲酸苄酯。反应优选在低于-20℃的降低的温度下。所得溶液可用氯化铵淬灭并还原成残余物。然后可将残余物再溶解在有机溶剂中，洗涤，干燥并重结晶以纯化化合物。

2. 发明授权

US5750736A Method for acylating 10-deacetylbaccatin III selectively at the c-10 position 失效
标题翻译：在c-10位选择性地酰化10-脱乙酰基浆果赤霉素III的方法
公开(公告)号：US5750736A
公开(公告)日：1998-05-12
申请号：US678759
申请日：1996-07-11
申请人： Nicholas J. Sisti
发明人： Nicholas J. Sisti
IPC分类号： C07D305/14
CPC分类号： C07D305/14
摘要： A method of acylating 10-deacetylbaccatin III at the C-10 position over the C-7 hydroxy position thereof to produce baccatin III is accomplished first by dissolving 10-deacetylbaccatin III in an anhydrous ether solvent, such as tetrahydrofuran, at a reduced temperature, preferably -78.degree. C. At least an equivalent of a lithium base, preferably about two equivalents n-butyl lithium, is next added followed by the addition of an acylating agent, such as acetyl chloride. The resulting solution is quenched, for example with ammonium chloride, to eliminate excess of the lithium base and the acylating agent. The result is baccatin III in solution. The baccatin III may be recovered by removing the ether solvent under vacuum to produce a residue that may then be dissolved, for example in ethyl acetate, with this solution being washed to remove unwanted salt compounds. Recrystallization and column chromatography may be employed to purify the baccatin III.
摘要翻译：首先通过将10-脱乙酰基浆果赤霉素III溶解在无水醚溶剂如四氢呋喃中，在还原温度下完成在C-7位羟基上将10-脱乙酰基浆果赤霉素III酰化生成浆果赤霉素III的方法，优选-78℃。随后加入至少一当量的锂碱，优选约2当量的正丁基锂，随后加入酰化剂如乙酰氯。所得溶液例如用氯化铵淬灭，以除去过量的锂碱和酰化剂。结果是溶液中的浆果赤霉素III。可以通过在真空下除去醚溶剂来回收浆果赤霉素III，以产生可以溶解的残余物，例如在乙酸乙酯中，洗涤该溶液以除去不需要的盐化合物。可以使用重结晶和柱色谱来纯化浆果赤霉素III。

3. 发明授权

US6143902A C-2 hydroxyl protected-N-acyl (2R,3S)-3-phenylisoserine N-imido activated esters and method for production thereof 失效
标题翻译： C-2羟基保护-N-酰基（2R，3S）-3-苯基异丝氨酸N-酰亚胺活化酯及其制备方法
公开(公告)号：US6143902A
公开(公告)日：2000-11-07
申请号：US336962
申请日：1999-06-21
申请人： Jan Zygmunt , James D. McChesney , Madhavi C. Chander
发明人： Jan Zygmunt , James D. McChesney , Madhavi C. Chander
IPC分类号： C07D207/40 , C07D207/404 , C07D207/44 , C07D207/448 , C07D209/48 , C07D209/52 , C07D209/76 , C07D305/14 , C07D207/444 , C07D209/34 , C07D209/56
CPC分类号： C07D207/404 , C07D207/448 , C07D209/48 , C07D209/52 , C07D209/76 , C07D305/14 , Y02P20/55
摘要： A chemic compound having the formula: ##STR1## wherein P.sub.1 is a hydroxyl protecting group, R.sub.1 is an alkyl group, an olefinic group, an aromatic group, Ph, PhCH.sub.2, an O-alkyl group, an O-olefinic group, an O-aromatic group, O--Ph, or O--CH.sub.2 Ph, and wherein Z is an N-imido group. In particular, P.sub.1 may be selected from the group consisting of benzyl, benzyloxymethyl and benzoyl, and Z may be a heterocyclic N-imido group, preferably having 5 to 7 atoms in the ring and alternatively substituted with at least one electron withdrawing group, preferably selected from the group consisting of a chloro group, a fluoro group and a nitro group. In particular, it is contemplated that Z may be succinimido, phthalimido, 5-norbornene-2,3-dicarboxyimido, maleimido and substituted derivatives thereof.
摘要翻译：具有下式的化学化合物：其中P1是羟基保护基，R1是烷基，烯基，芳基，Ph，PhCH2，O-烷基，O-烯烃基，O-芳族基，O-Ph或O-CH 2 Ph，其中Z为N-亚氨基。特别地，P1可以选自苄基，苄氧基甲基和苯甲酰基，Z可以是杂环N-酰亚胺基，优选在环中具有5至7个原子，或者替代地被至少一个吸电子基团取代选自氯基，氟基和硝基。特别地，预期Z可以是琥珀酰亚胺基，邻苯二甲酰亚氨基，5-降冰片烯-2,3-二羧酰亚氨基，马来酰亚胺及其取代的衍生物。

4. 发明授权

US6136999A C-2 hydroxyl protected-n-acyl (2R,3S)-3-phenylisoserine substituted phenyl activated esters and method for production thereof 失效
标题翻译： C 2羟基保护的正己酰基（2R，3S）-3-苯基异丝氨酸取代的苯基活性酯及其制备方法
公开(公告)号：US6136999A
公开(公告)日：2000-10-24
申请号：US336961
申请日：1999-06-21
申请人： Madhavi C. Chander , James D. McChesney , Jan Zygmunt
发明人： Madhavi C. Chander , James D. McChesney , Jan Zygmunt
IPC分类号： C07C233/47 , C07C233/51 , C07C233/87 , C07C271/22 , C07C229/08 , C07D305/14
CPC分类号： C07C233/87 , C07C233/47 , C07C233/51 , C07C271/22 , Y02P20/55
摘要： A chemical compound having the formula: ##STR1## wherein P.sub.1 is a hydroxyl protecting group, R.sub.1 may be H or electron withdrawing group, R.sub.2 may be H or electron withdrawing group, R.sub.3 may be H or electron withdrawing group, R.sub.4 may be H or electron withdrawing group, R.sub.5 may be H or electron withdrawing group, R.sub.6 may be an alkyl group, an olefinic group, an aromatic group, Ph, PhCH.sub.2, an O-alkyl group, an O-olefinic group, an O-aromatic group, O--Ph, or O--CH.sub.2 Ph.
摘要翻译：具有下式的化合物：其中P1是羟基保护基，R 1可以是H或吸电子基团，R 2可以是H或吸电子基团，R 3可以是H或吸电子基团，R 4可以是H或吸电子基团 R 5可以是H或吸电子基团，R6可以是烷基，烯基，芳基，Ph，PhCH2，O-烷基，O-烯烃基，O-芳族基，O-Ph ，或O-CH 2 Ph。

5. 发明授权

US5688517A Method for assessing sensitivity of tumor cells to cephalomannine and 10-deacetyltaxol 失效
标题翻译：评估肿瘤细胞对头孢麻黄碱和10-脱乙酰紫杉醇敏感性的方法
公开(公告)号：US5688517A
公开(公告)日：1997-11-18
申请号：US10821
申请日：1993-01-29
申请人： Lawrence Helson , Sterling K. Ainsworth
发明人： Lawrence Helson , Sterling K. Ainsworth
IPC分类号： G01N33/50 , A61F13/00
CPC分类号： G01N33/5011 , Y10S436/815
摘要： A method for assessing the sensitivity of a patient's tumor cells to cephalomannine and 10-deacetyltaxol in order to treat those tumor cells involves the removal of a sample of the tumor cells and establishing a cell line therefrom. Cells from the cell line are cultured and then contacted with varying concentrations of cephalomannine or 10-deacetyltaxol to form treated cells. The treated cells are assessed to determine the cytotoxic effect of the cephalomannine and/or the 10-deacetyltaxol and, where cytotoxic response is exhibited, a therapeutic dosage is formulated using the selected concentration of cephalomannine or 10-deacetyltaxol and a carrier material. The method is particularly useful for neural and glial tumor cells.
摘要翻译：用于评估患者肿瘤细胞对头孢霉宁和10-脱乙酰紫杉醇以治疗这些肿瘤细胞的敏感性的方法包括去除肿瘤细胞的样品并从其中建立细胞系。培养来自细胞系的细胞，然后与不同浓度的头孢麻黄碱或10-脱乙酰紫杉醇接触以形成处理的细胞。评估处理的细胞以确定头孢麻黄碱和/或10-脱乙酰紫杉醇的细胞毒性作用，并且在显示细胞毒性反应的情况下，使用所选浓度的头孢麻黄碱或10-脱乙酰紫杉醇和载体材料配制治疗剂量。该方法对于神经和神经胶质瘤细胞特别有用。

6. 发明授权

US5202448A Processes of converting taxanes into baccatin III 失效
标题翻译：将紫杉烷转化为浆果赤霉素III的方法
公开(公告)号：US5202448A
公开(公告)日：1993-04-13
申请号：US930840
申请日：1992-08-14
申请人： David R. Carver , Timothy R. Prout , Hernita A. Ewald , Donia L. Henderson
发明人： David R. Carver , Timothy R. Prout , Hernita A. Ewald , Donia L. Henderson
IPC分类号： C07D305/14
CPC分类号： C07D305/14
摘要： The present invention relates to a process of converting partially purified taxane mixtures into Baccatin III. The process for the preparation of Baccatin III includes contacting a mixture containing at least one taxane compound having an ester linkage at the C-13 position with at least one borohydride reducing salt in a reaction solvent in the present of a Lewis acid.
摘要翻译：本发明涉及将部分纯化的紫杉烷混合物转化为浆果赤霉素III的方法。制备浆果赤霉素III的方法包括在路易斯酸存在的反应溶剂中使包含至少一种在C-13位具有酯键的紫杉烷化合物与至少一种硼氢化物还原盐的混合物接触。

7. 发明授权

US6066749A Method for conversion of C-2'-O-protected-10-hydroxy taxol to c-2'-O-protected taxol:useful intermediates in paclitaxel synthesis 失效
标题翻译：将C-2'-O-保护的10-羟基紫杉醇转化为c-2'-O保护的紫杉醇的方法：紫杉醇合成中的有用中间体
公开(公告)号：US6066749A
公开(公告)日：2000-05-23
申请号：US71261
申请日：1998-05-01
申请人： Nicholas J. Sisti , Herbert R. Brinkman , James D. McChesney , Madhavi C. Chander , Xian Liang , Jan Zygmunt
发明人： Nicholas J. Sisti , Herbert R. Brinkman , James D. McChesney , Madhavi C. Chander , Xian Liang , Jan Zygmunt
IPC分类号： C07D305/14
CPC分类号： C07D305/14
摘要： A method of acylating C-2' O-protected-10-hydroxy taxol selectively at the C-10 hydroxyl position over the C-7 hydroxy position thereof to produce C-2' O-protected taxol is accomplished first by dissolving C-2' O-protected-10-hydroxy taxol in an acceptable ether solvent therefor, such as tetrahydrofuran, to form a first solution at a first temperature. The first solution is then cooled to a second temperature, and a lithium base, preferably n-butyl lithium, is added to form an intermediate compound having a lithium alkoxide at the C-10 position thereof. An acylating agent, such as acetyl chloride, is then added. The resulting solution may be quenched, for example with ammonium chloride, to eliminate excess of the acylating agent and the lithium base. The result is a solution containing C-2' O-protected taxol. This solution may then be washed, concentrated and purified. The present invention is also directed to C-10 lithium alkoxide intermediate compounds for the production of paclitaxel.
摘要翻译：首先通过将C-2'O-保护的10-羟基紫杉醇溶解在C-10羟基的C- 在其可接受的醚溶剂如四氢呋喃中的O-保护的10-羟基紫杉醇在第一温度下形成第一溶液。然后将第一溶液冷却至第二温度，并加入锂碱，优选正丁基锂以形成其C-10位上具有锂醇盐的中间体化合物。然后加入酰化剂，如乙酰氯。所得溶液可以例如用氯化铵淬灭，以消除过量的酰化剂和锂碱。其结果是含有C-2'O保护的紫杉醇的溶液。然后可以将该溶液洗涤，浓缩并纯化。本发明还涉及用于生产紫杉醇的C-10锂盐中间体化合物。

8. 发明授权

US6048990A Method for selective acylation of C-2'-O-protected-10-hydroxy-taxol at the C-10 position 失效
标题翻译：在C-10位置选择性酰化C-2'-O-保护的10-羟基 - 紫杉醇的方法
公开(公告)号：US6048990A
公开(公告)日：2000-04-11
申请号：US71258
申请日：1998-05-01
申请人： Xian Liang , Jan Zygmunt , Nicholas J. Sisti , Madhavi C. Chander , Herbert R. Brinkman , James D. McChesney
发明人： Xian Liang , Jan Zygmunt , Nicholas J. Sisti , Madhavi C. Chander , Herbert R. Brinkman , James D. McChesney
IPC分类号： C07D305/14
CPC分类号： C07D305/14
摘要： A method of acylating C-2' O-protected-10-hydroxy taxol selectively at the C-10 hydroxyl position over the C-7 hydroxy position thereof to produce C-2' O-protected taxol is accomplished first by dissolving C-2' O-protected-10-hydroxy taxol in an acceptable ether solvent therefor, such as tetrahydrofuran. A lithium salt, preferably lithium chloride, is added. A trialkylamine base or pyridine is next added, followed by the addition of an acylating agent, such as acetyl chloride. The resulting solution may be quenched, for example with ammonium chloride, to eliminate excess of the acylating agent. This solution may then be diluted with ethyl acetate to form an organic phase and an aqueous phase, with the organic phase being washed and thereafter reduced. Recrystallization and column chromatography may be employed to purify the C-2' O-protected taxol.
摘要翻译：首先通过将C-2'O-保护的10-羟基紫杉醇溶解在C-10羟基的C- 'O-保护的10-羟基紫杉醇在其可接受的醚溶剂中，例如四氢呋喃。加入锂盐，优选氯化锂。然后加入三烷基胺碱或吡啶，然后加入酰化剂如乙酰氯。所得溶液可以例如用氯化铵淬灭，以消除过量的酰化剂。然后可以用乙酸乙酯稀释该溶液以形成有机相和水相，同时洗涤有机相，然后还原。可以使用重结晶和柱色谱来纯化C-2'O保护的紫杉醇。

9. 发明授权

US5684175A C-2' hydroxyl-benzyl protected, N-carbamate protected (2R, 3S)- 3-phenylisoserine and production process therefor 失效
标题翻译： C-2'羟基 - 苄基保护的N-氨基甲酸酯保护的（2R，3S）-3-苯基异丝氨酸及其制备方法
公开(公告)号：US5684175A
公开(公告)日：1997-11-04
申请号：US483081
申请日：1995-06-07
申请人： Nicholas J. Sisti , Charles S. Swindell , Madhavi C. Chander
发明人： Nicholas J. Sisti , Charles S. Swindell , Madhavi C. Chander
IPC分类号： C07C269/06 , C07C271/22 , C07D305/14 , C07F7/18 , C07C271/00
CPC分类号： C07D305/14 , C07C271/22 , C07F7/1856 , C07B2200/07 , Y02P20/55
摘要： The synthesis of paclitaxel obtained from the semi-synthesis of taxol using a protected baccatin III backbone which is esterified with a suitably protected side chain acid, thereby producing an intermediate which may be acylated and deprotected to produce paclitaxel.
摘要翻译：使用得自保护的浆果赤霉素III骨架的紫杉醇的半合成得到的紫杉醇的合成，其用适当保护的侧链酸酯化，从而产生可被酰化和去保护以产生紫杉醇的中间体。

10. 发明授权

US5256801A Processes of converting taxanes into 10-deacetylbaccatin III 失效
标题翻译：将紫杉烷类转化为10-脱乙酰基浆果赤霉素III的方法
公开(公告)号：US5256801A
公开(公告)日：1993-10-26
申请号：US986852
申请日：1992-12-04
申请人： David R. Carver , Timothy R. Prout , Hernita A. Ewald , Donia L. Henderson
发明人： David R. Carver , Timothy R. Prout , Hernita A. Ewald , Donia L. Henderson
IPC分类号： C07D305/14
CPC分类号： C07D305/14
摘要： A process for the preparation of a compound of formula (I) ##STR1## comprising contacting a mixture containing at least one taxane compound having an ester linkage at the C-13 position with at least one borohydride reducing salt in a reaction solvent in the presence of a Lewis acid.
摘要翻译：一种制备式（I）化合物的方法＆lt; IMAGE＆gt;包括在含有至少一种具有C-13位的酯键的紫杉烷化合物与至少一种硼氢化还原盐的反应溶剂中，在存在的路易斯酸。

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