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1. 发明授权

US6137009A Method of manufacturing flumetralin 有权
标题翻译：氟美他啶的制备方法
公开(公告)号：US6137009A
公开(公告)日：2000-10-24
申请号：US416543
申请日：1999-10-12
申请人： Stefan Kwiatkowski , Steven G. Mobley , Kryzsztof Pupek , Miroslaw Golinski , Paul D. Smith
发明人： Stefan Kwiatkowski , Steven G. Mobley , Kryzsztof Pupek , Miroslaw Golinski , Paul D. Smith
IPC分类号： C07C209/08 , C07C211/29 , C07C209/00
CPC分类号： C07C209/08
摘要： The invention is a process to manufacture the intermediate secondary amine N-ethyl-2-chloro-6-fluoro-benzylamine, and then the process of reacting this intermediate to manufacture the herbicide flumetralin. Equimolar quantities of monoethylamine, sodium hydroxide, and 2-chloro-6-fluorobenzyl chloride are reacted at a temperature between about 70.degree. C. and about 100.degree. C. in a composition containing at least 2.5 times the required quantity of monoethylamine. The reagent monoethylamine functions as solvent and heat sink for the reaction, and also minimizes the formation of undesired byproducts. The excess monoethylamine is removed after formation of the intermediate. Then, equimolar quantities of sodium hydroxide in water and molten 4-chloro-3-5-dinitrobenzotrifluoride are added to the intermediate, and the temperature is controlled between about 90.degree. C. and about 115.degree. C. The product of this reaction is relatively pure, i.e., 98 percent by weight, molten flumetralin. It is advantageous to wash the product with boiling water to facilitate removal of salt and excess sodium hydroxide.
摘要翻译：本发明是制备中间仲胺N-乙基-2-氯-6-氟 - 苄胺的方法，然后是使该中间体反应以制备除草剂氟马特林的方法。将等摩尔量的单乙胺，氢氧化钠和2-氯-6-氟苄基氯在约70℃至约100℃的温度下在含有至少2.5倍所需量的单乙胺的组合物中反应。试剂单乙胺用作反应的溶剂和散热器，并且还使不期望的副产物的形成最小化。在形成中间体之后除去过量的单乙胺。然后，将等摩尔量的氢氧化钠水溶液和熔融的4-氯-3,5-二硝基三氟甲苯加入到中间体中，温度控制在约90℃至约115℃之间。该反应的产物相对纯的，即98重量％的熔融氟汞。用沸水洗涤产品以便于除去盐和过量的氢氧化钠是有利的。

2. 发明授权

US06872831B2 Carboxylated heterocyclic compounds and methods of synthesis 失效
公开(公告)号：US06872831B2
公开(公告)日：2005-03-29
申请号：US10749839
申请日：2003-12-31
申请人： Stefan Kwiatkowski , Miroslaw Golinski
发明人： Stefan Kwiatkowski , Miroslaw Golinski
IPC分类号： C07D215/36
CPC分类号： C07D215/36
摘要： Compositions of the present invention comprise carboxylated heterocyclic compounds, including carboxyflosequinan. The methods of the present invention also comprise the synthesis of carboxyflosequinan.

3. 发明授权

US07084275B2 Stereospecific enrichment of heterocyclic enantiomers 失效
公开(公告)号：US07084275B2
公开(公告)日：2006-08-01
申请号：US10715904
申请日：2003-11-18
申请人： Stefan Kwiatkowski , Miroslaw Golinski , Joseph Kupper
发明人： Stefan Kwiatkowski , Miroslaw Golinski , Joseph Kupper
IPC分类号： C07D215/02
CPC分类号： C07D215/36 , C07B2200/07 , Y02P20/582
摘要： The present invention describes methods for the stereoselective synthesis of heterocyclic enantiomers. The methods of the present invention incorporate the stereo-preferred oxidation of quinolone thiomethyl intermediates by optically active camphor based oxaziridines to provide R(+) or S(−) quinolone methylsulfinyl derivatives.

4. 发明授权

US06767914B2 Fluorinated heterocyclic compounds and methods of synthesis 失效
标题翻译：氟化杂环化合物及其合成方法
公开(公告)号：US06767914B2
公开(公告)日：2004-07-27
申请号：US10281801
申请日：2002-10-28
申请人： Stefan Kwiatkowski , Miroslaw Golinski
发明人： Stefan Kwiatkowski , Miroslaw Golinski
IPC分类号： A61K3147
CPC分类号： A61K31/4704 , C07D215/36
摘要： Compositions of the present invention comprise fluorinated heterocyclic compounds, including monofluoroflosequinan and difluoroflosequinan. The methods of the present invention comprise the synthesis of monofluoroflosequinan and difluoroflosequinan.
摘要翻译：本发明的组合物包括氟化杂环化合物，包括单氟聚苯乙烯和二氟佛质素。本发明的方法包括合成单氟代聚苯并an嗪和二氟佛硫酮。

5. 发明授权

US06730790B2 Chlorinated heterocyclic compounds and methods of synthesis 失效
公开(公告)号：US06730790B2
公开(公告)日：2004-05-04
申请号：US10281684
申请日：2002-10-28
申请人： Stefan Kwiatkowski , Miroslaw Golinski
发明人： Stefan Kwiatkowski , Miroslaw Golinski
IPC分类号： A61K3147
CPC分类号： C07D215/36
摘要： Compositions of the present invention comprise chlorinated heterocyclic compounds, including racemic monochloroflosequinan, purified enantiomers of monochloroflosequinan and the sulfone derivative of monochloroflosequinan. The methods of the present invention comprise the synthesis of racemic monochloroflosequinan and derivatives thereof, including the sulfone derivative. Intermediates in the synthesis are also provided. The methods further comprise the synthesis of enantiomers of monochloroflosequinan.

6. 发明申请

US20070010676A1 Stereospecific enrichment of heterocyclic enantiomers 审中-公开
标题翻译：杂环对映体的立体特异性富集
公开(公告)号：US20070010676A1
公开(公告)日：2007-01-11
申请号：US11412649
申请日：2006-04-27
申请人： Stefan Kwiatkowski , Miroslaw Golinski , Joseph Kupper
发明人： Stefan Kwiatkowski , Miroslaw Golinski , Joseph Kupper
IPC分类号： A61K31/4704
CPC分类号： C07D215/36 , C07B2200/07 , Y02P20/582
摘要： The present invention describes methods for the stereoselective synthesis of heterocyclic enantiomers. The methods of the present invention incorporate the stereo-preferred oxidation of quinolone thiomethyl intermediates by optically active camphor based oxaziridines to provide R(+) or S(−) quinolone methylsulfinyl derivatives.
摘要翻译：本发明描述了立体选择性合成杂环对映异构体的方法。本发明的方法通过光学活性樟脑氧氮杂环丁烷引入喹诺酮硫代甲基中间体的立体优选氧化，得到R（+）或S（ - ）喹诺酮甲基亚磺酰基衍生物。

7. 发明授权

US07045627B2 Dichlorinated heterocyclic compounds and methods of synthesis 失效
公开(公告)号：US07045627B2
公开(公告)日：2006-05-16
申请号：US11132115
申请日：2005-05-17
申请人： Stefan Kwiatkowski , Miroslaw Golinski
发明人： Stefan Kwiatkowski , Miroslaw Golinski
IPC分类号： C07D215/36
CPC分类号： A61K31/47 , C07D215/36
摘要： Compositions of the present invention comprise dichlorinated heterocyclic compounds, including dichloroflosequinan. The methods of the present invention also comprise the synthesis of dichloroflosequinan.

8. 发明授权

US06894166B2 Dichlorinated heterocyclic compounds and methods of synthesis 失效
公开(公告)号：US06894166B2
公开(公告)日：2005-05-17
申请号：US10781451
申请日：2004-02-18
申请人： Stefan Kwiatkowski , Miroslaw Golinski
发明人： Stefan Kwiatkowski , Miroslaw Golinski
IPC分类号： A61K31/47 , C07D215/16 , C07D215/36
CPC分类号： A61K31/47 , C07D215/36
摘要： Compositions of the present invention comprise dichlorinated heterocyclic compounds, including dichloroflosequinan. The methods of the present invention also comprise the synthesis of dichloroflosequinan.

9. 发明申请

US20050032833A1 Fluorinated heterocyclic compounds and methods of synthesis 失效
标题翻译：氟化杂环化合物及其合成方法
公开(公告)号：US20050032833A1
公开(公告)日：2005-02-10
申请号：US10849606
申请日：2004-05-20
申请人： Stefan Kwiatkowski , Miroslaw Golinski
发明人： Stefan Kwiatkowski , Miroslaw Golinski
IPC分类号： C07D215/36 , A61K31/47
CPC分类号： A61K31/4704 , C07D215/36
摘要： Compositions of the present invention comprise fluorinated heterocyclic compounds, including monofluoroflosequinan and difluoroflosequinan. The methods of the present invention comprise the synthesis of monofluoroflosequinan and difluoroflosequinan.
摘要翻译：本发明的组合物包括氟化杂环化合物，包括单氟聚苯乙烯和二氟佛质素。本发明的方法包括合成单氟代聚苯并an嗪和二氟佛硫酮。

10. 发明申请

US20070010552A1 Fluorinated heterocyclic compounds and methods of synthesis 审中-公开
标题翻译：氟化杂环化合物及其合成方法
公开(公告)号：US20070010552A1
公开(公告)日：2007-01-11
申请号：US11410357
申请日：2006-04-25
申请人： Stefan Kwiatkowski , Miroslaw Golinski
发明人： Stefan Kwiatkowski , Miroslaw Golinski
IPC分类号： A61K31/4704
CPC分类号： A61K31/4704 , C07D215/36
摘要： Compositions of the present invention comprise fluorinated heterocyclic compounds, including monofluoroflosequinan and difluoroflosequinan. The methods of the present invention comprise the synthesis of monofluoroflosequinan and difluoroflosequinan.
摘要翻译：本发明的组合物包括氟化杂环化合物，包括单氟聚苯乙烯和二氟佛质素。本发明的方法包括合成单氟代聚苯并an嗪和二氟佛硫酮。

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