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1. 发明授权

US5290560A Extrusion of an admixture of a meltable binder and a food or drug 失效
标题翻译：挤出可熔融粘合剂和食品或药物的混合物
公开(公告)号：US5290560A
公开(公告)日：1994-03-01
申请号：US719039
申请日：1991-06-21
申请人： Pierre Autant , Jacques Ruel , Stephen Weinhold , Charles A. McCombs , Ernest P. Smith , Stephen H. Wu , Louis P. Hoskins
发明人： Pierre Autant , Jacques Ruel , Stephen Weinhold , Charles A. McCombs , Ernest P. Smith , Stephen H. Wu , Louis P. Hoskins
IPC分类号： A23K1/18 , A23K1/00 , A61K9/16 , A61K31/195 , A61K47/44 , A61P3/00
CPC分类号： A61K9/1617 , A23K40/35 , Y10S426/807
摘要： The present invention relates to new granules, as well as the process for their preparation, obtained by extrusion of a mixture containing a meltable binder in an amount such that it permits the passage of the mixture through a die. The granules obtained are then coated with a polymer permitting their trans-rumen passage without degradation. After coating, these granules are used for animal feeding of ruminants.
摘要翻译：本发明涉及新的颗粒，以及它们的制备方法，其通过挤出包含可熔粘合剂的混合物获得，其量使其允许混合物通过模头。然后将所获得的颗粒用聚合物包被，其允许其经转运通道而不降解。涂布后，将这些颗粒用于反刍动物饲养。

2. 发明授权

US4945178A Preparation of 4-carboalkoxy-1,3-cyclohexanedione type compounds 失效
标题翻译： 4-烷氧基-1,3-环己二酮型化合物的制备
公开(公告)号：US4945178A
公开(公告)日：1990-07-31
申请号：US314994
申请日：1989-02-24
申请人： Charles A. McCombs
发明人： Charles A. McCombs
IPC分类号： C07C67/347
CPC分类号： C07C319/20 , C07C2101/14
摘要： Acetoacetic esters of the formula R--OOCCH.sub.2 COCH.sub.3 are reacted with an unsaturated ester of the formula R.sup.1 R.sup.2 C.dbd.CHCOOR.sup.3 in the presence of basic catalyst such as ethanolic sodium ethoxide to give compound I of the formula ##STR1## and the alcohol by-product HOR.sup.3. By known hydrolysis and decarboxylation procedures, compound I is convertible to compound II of the formula ##STR2## In the above formulas, R is alkyl, R.sup.1 and R.sup.2 are each selected independently from H, alkyl, alkylthioalkyl, cycloalkyl, alkyl substituted cycloalkyl, aryl, substituted aryl, heterocyclic, or substituted heterocyclic, and R.sup.3 is alkyl or cycloalkyl. These compounds I and II are intermediates in the preparation of known herbicides.
摘要翻译：式R-OOCCH 2 COCH 3的乙酰乙酸酯与式R 1 R 2 C = CHCOOR 3的不饱和酯在碱性催化剂如乙醇乙醇钠的存在下反应，得到式（I）化合物I和醇副产物 HOR3。通过已知的水解和脱羧方法，化合物I可转化成式（II）的化合物II在上式中，R是烷基，R 1和R 2各自独立地选自H，烷基，烷硫基烷基，环烷基，烷基取代环烷基，芳基，取代的芳基，杂环或取代的杂环，并且R 3是烷基或环烷基。这些化合物I和II是制备已知除草剂的中间体。

3. 发明授权

US5359126A Organic compositions and their manufacture 失效
标题翻译：有机成分及其制造
公开(公告)号：US5359126A
公开(公告)日：1994-10-25
申请号：US192518
申请日：1994-02-07
申请人： Charles A. McCombs
发明人： Charles A. McCombs
IPC分类号： C07C67/347 , C07C69/74
CPC分类号： C07C67/347
摘要： Preparing cyclohexanediones of the formula ##STR1## an aldehyde is reacted with a ketene to give a polymer having the repeating unit ##STR2## wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3. The unsaturated ester is contacted with a basic catalyst to cyclize it to the cyclic dione ester of the formula ##STR3## and this ester is then hydrolyzed and decarboxylated to give the cyclohexanedione give the productwherein:R is selected, e.g., from alkylthio, alkylthioalkyl, cycloalkyl, alkyl substituted cycloalkyl, alkoxy, alkanoyloxy, alkoxycarbonyl, aryl, suhstituted aryl, heterocyclic, or substituted heterocyclic, wherein each group or moiety has up to 20 carbons; andR.sub.1, R.sub.2 and R.sub.3 are each selected, e.g., from alkyl or cycloalkyl of up to 20 carbons, and R.sub.2 and R.sub.3 can also be hydrogen.
摘要翻译：制备式（Ⅰa）醛的环己二酮与乙烯酮反应得到具有重复单元的聚合物，其中n为约2至约1,000。将聚合物水解以产生式R-CH = C（R 1）-COOH的不饱和酸与式R-CH（OH）C（R 1）（R 2）-COOR 3的羟基酯或酸的混合物，然后将混合物与酯化剂接触以将酸转化成酯。将酯混合物与脱水剂接触以将羟基酯转化为式R-CH = C（R 1）-COOR 3的不饱和酯。使不饱和酯与碱性催化剂接触以使其与式“IMAGE”的环状二酮酯环化，然后将该酯水解和脱羧，得到环己烷二酮，得到其中：R选自例如烷硫基，烷硫基烷基环烷基，烷基取代的环烷基，烷氧基，烷酰氧基，烷氧基羰基，芳基，取代的芳基，杂环或取代的杂环，其中每个基团或部分具有至多20个碳原子; 并且R 1，R 2和R 3各自选自例如至多20个碳的烷基或环烷基，并且R 2和R 3也可以是氢。

4. 发明授权

US5117016A Method for obtaining a stigmasterol enriched product from deodorizer distillate 失效
标题翻译：从除臭馏分中获得豆甾醇富集产物的方法
公开(公告)号：US5117016A
公开(公告)日：1992-05-26
申请号：US699021
申请日：1991-05-13
申请人： Tommy L. Tackett , Charles A. McCombs
发明人： Tommy L. Tackett , Charles A. McCombs
IPC分类号： C07J9/00
CPC分类号： C07J9/00
摘要： A method for obtaining a stigmasterol enriched product from esterified deodorizer distillate by use of a particular solvent system. The solvent system contains water, a C.sub.1 to C.sub.6 alcohol such as methanol, and a non-polar solvent such as heptane.
摘要翻译：一种通过使用特定的溶剂体系从酯化除臭馏分中获得豆甾醇富集产物的方法。溶剂系统含有水，C1至C6醇如甲醇，以及非极性溶剂如庚烷。

5. 发明授权

US5225589A Organic compositions and their manufacture 失效
标题翻译：有机成分及其制造
公开(公告)号：US5225589A
公开(公告)日：1993-07-06
申请号：US829640
申请日：1992-02-03
申请人： Charles A. McCombs
发明人： Charles A. McCombs
IPC分类号： C07C67/347
CPC分类号： C07C67/347
摘要： Processes, intermediates, and products involved in preparing cyclohexanediones of the formula ##STR1## are disclosed. An aldehyde of the formula R--CHO is reacted with a ketene type compound of the formula (R.sub.1)(R.sub.2)C.dbd.C.dbd.O at a temperature below about 110.degree. C. to give a polymer having the repeating unit ##STR2## wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed with alcoholic or aqueous base to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3. The unsaturated ester is contacted with a basic catalyst to cyclize it to the cyclic dione ester of the formula ##STR3## this ester is then hydrolyzed and decarboxylated to give the product ##STR4## wherein: R is selected, e.g., from alkylthio, alkylthioalkyl, cycloalkyl, alkyl substituted cycloalkyl, alkoxy, alkanoyloxy, alkoxycarbonyl, aryl, substituted aryl, heterocyclic, or substituted heterocyclic, wherein each group or moiety has up to 20 carbons; andR.sub.1, R.sub.2 and R.sub.3 are each selected, e.g., from alkyl or cycloalkyl of up to 20 carbons, and R.sub.2 and R.sub.3 can also be hydrogen.
摘要翻译：公开了涉及制备式“IMAGE”的环己二酮的方法，中间体和产物。在低于约110℃的温度下，将式R-CHO的醛与式（R1）（R2）C = C = O的烯酮类化合物反应，得到具有重复单元的聚合物，其中 n的范围为约2至约1,000。聚合物用醇或碱水溶液水解以产生式R-CH = C（R 1）-COOH的不饱和酸与式R-CH（OH）C（R 1）的羟基酯或酸的混合物 R2）-COOR3，然后将混合物与酯化剂接触以将酸转化成酯。将酯混合物与脱水剂接触以将羟基酯转化为式R-CH = C（R 1）-COOR 3的不饱和酯。不饱和酯与碱性催化剂接触以将其环化成式的环状二酮酯，然后将该酯水解和脱羧，得到产物，其中：R选自例如烷硫基，烷硫基烷基，环烷基，烷基取代的环烷基，烷氧基，烷酰氧基，烷氧基羰基，芳基，取代的芳基，杂环或取代的杂环，其中各基团或部分具有至多20个碳原子; 并且R 1，R 2和R 3各自选自例如至多20个碳的烷基或环烷基，并且R 2和R 3也可以是氢。

6. 发明授权

US4588683A Method of preparing 11.beta., 17.alpha., 20, 21-tetrahydroxy steroids and corresponding 11.beta., 17.alpha., 21-trihydroxy-20-oxo steroids 失效
标题翻译：制备11β，17α，20,21-四羟基类固醇和相应的11β，17α，21-三羟基-20-氧代类固醇的方法
公开(公告)号：US4588683A
公开(公告)日：1986-05-13
申请号：US577467
申请日：1984-02-06
申请人： Charles T. Goodhue , Gwendolyn C. Kydd , Charles H. Foster , Charles A. McCombs
发明人： Charles T. Goodhue , Gwendolyn C. Kydd , Charles H. Foster , Charles A. McCombs
IPC分类号： C07J5/00 , C12P33/08 , C12R1/645
CPC分类号： C12P33/08 , C07J5/0053 , Y10S435/911
摘要： Disclosed herein is a method for preparing 11.beta., 17.alpha., 20, 21-tetrahydroxy steroids of the pregnane class. This method comprises incubating the corresponding 17.alpha., 20.alpha. or .beta., 21-trihydroxy steroid in the presence of a culture medium capable of effecting the 11.beta.-hydroxylation, such medium comprising a fungal culture of the genus Curvularia. Also disclosed herein is a method for preparing 11.beta., 17.alpha., 21-trihydroxy-20-oxo steroids of the pregnane class. This method comprises the hydroxylation method described hereinabove followed by conversion of the resulting 11.beta., 17.alpha., 20.alpha. or .beta., 21-tetrahydroxy steroid into the corresponding 11.beta., 17.alpha., 21-trihydroxy-20-oxo steroid.
摘要翻译：本文公开了一种制备孕烷类的11β，17α，20,21-四羟基类固醇的方法。该方法包括在能够进行11β-羟基化的培养基存在下孵育相应的17α，20α或β，21-三羟基类固醇，这种培养基包括曲霉属真菌培养物。本文还公开了制备孕烷类的11β，17α，21-三羟基-20-氧代甾族化合物的方法。该方法包括上文所述的羟基化方法，随后将所得的11β，17α，20α或β21-二羟基类固醇转化成相应的11β，17α，21-三羟基-20-氧代甾族化合物。

7. 发明授权

US5693850A Nutritive water soluble glycerol esters of hydroxy butyric acid 失效
标题翻译：营养水溶性甘油酯的羟基丁酸
公开(公告)号：US5693850A
公开(公告)日：1997-12-02
申请号：US470399
申请日：1995-06-06
申请人： Ronald H. Birkhahn , Robert J. Clemens , Charles A. McCombs
发明人： Ronald H. Birkhahn , Robert J. Clemens , Charles A. McCombs
IPC分类号： A61K31/22 , C07C69/675 , C07C69/66
CPC分类号： C07C69/675 , A61K31/22
摘要： A process for the production of water soluble glycerol esters useful as parenteral nutrients is disclosed. The process comprises the reaction of glycerol or a protected glycerol and an acetoacetate ester or acetoacetate precursor, yielding an acetoacetyl glycerol which is thereafter reduced, providing a glycerol ester of 3-hydroxybutyric acid.
摘要翻译：公开了用作生产用作肠胃外营养物的水溶性甘油酯的方法。该方法包括甘油或受保护的甘油与乙酰乙酸酯或乙酰乙酸酯前体的反应，得到乙酰乙酰甘油，然后还原，得到3-羟基丁酸的甘油酯。

8. 发明授权

US5041613A Organic compositions and their manufacture 失效
标题翻译：有机成分及其制造
公开(公告)号：US5041613A
公开(公告)日：1991-08-20
申请号：US399790
申请日：1989-08-28
申请人： Charles A. McCombs
发明人： Charles A. McCombs
IPC分类号： C07C67/347
CPC分类号： C07C67/347
摘要： Processes, intermediates, and products involved in preparing cyclohexanediones of the formula ##STR1## are disclosed. An aldehyde of the formula R--CHO is reacted with a ketone type compound of the formula (R.sub.1)(R.sub.2)C.dbd.C.dbd.O at a temperature below about 110.degree. C. to give a polymer having the repeating unit --OCH(R)C(R.sub.1)(R.sub.2)CO].sub.n wherein n ranges from about 2 to about 1,000. The polymer is hydrolyzed with alcoholic or aqueous base to produce a mixture of an unsaturated acid of the formula R--CH.dbd.C(R.sub.1)--COOH and a hydroxy ester or acid of the formula R--CH(OH)C(R.sub.1)(R.sub.2)--COOR.sub.3, the mixture is then contacted with an esterifying agent to convert the acids to esters. The ester mixture is contacted with a dehydrating agent to convert the hydroxy ester to unsaturated ester of the formula R--CH.dbd.C(R.sub.1)--COOR.sub.3. The unsaturated ester is contacted with a basic catalyst to cyclize it to the cyclic dione ester of the formula ##STR2## and this ester is then hydrolyzed and decarboxylated to give the product ##STR3## wherein: R is selected, e.g., from alkylthio, alkythioalkyl, cycloalkyl, alkyl substituted cycloalkyl, alkoxy, alkanoyloxy, alkoxycarbonyl, aryl, substituted aryl, heterocyclic, or substituted heterocyclic, wherein each group or moiety has up to 20 carbons; andR.sub.1, R.sub.2 and R.sub.3 are each selected, e.g., from alkyl or cycloalkyl of up to 20 carbons, and R.sub.2 and R.sub.3 can also be hydrogen.
摘要翻译：公开了涉及制备式“IMAGE”的环己二酮的方法，中间体和产物。在低于约110℃的温度下，使式R-CHO的醛与式（R1）（R2）C = C = O的酮型化合物反应，得到具有重复单元-OCH（R ）C（R 1）（R 2）CO] n，其中n为约2至约1,000。聚合物用醇或碱水溶液水解以产生式R-CH = C（R 1）-COOH的不饱和酸与式R-CH（OH）C（R 1）的羟基酯或酸的混合物 R2）-COOR3，然后将混合物与酯化剂接触以将酸转化成酯。将酯混合物与脱水剂接触以将羟基酯转化为式R-CH = C（R 1）-COOR 3的不饱和酯。使不饱和酯与碱性催化剂接触以将其环化为式“IMAGE”的环状二酮酯，然后将该酯水解和脱羧，得到产物，其中：选自R，例如烷硫基，烷硫基烷基环烷基，烷基取代的环烷基，烷氧基，烷酰氧基，烷氧基羰基，芳基，取代的芳基，杂环或取代的杂环，其中每个基团或部分具有至多20个碳原子; 并且R 1，R 2和R 3各自选自例如至多20个碳的烷基或环烷基，并且R 2和R 3也可以是氢。

9. 发明授权

US4329294A Process for preparing 17.alpha.-hydroxy-20-ketosteroids 失效
标题翻译：制备17α-羟基-20-酮类固醇的方法
公开(公告)号：US4329294A
公开(公告)日：1982-05-11
申请号：US247951
申请日：1981-03-26
申请人： Charles A. McCombs
发明人： Charles A. McCombs
IPC分类号： C07J7/00 , C07J1/00
CPC分类号： C07J7/0045
摘要： In accordance with the present invention, 17.alpha.-hydroxy-20-ketosteroids are prepared by the oxidation of 20-ketosteriods, such as 3-methoxy-pregna-3,5-dien-20-one. The 3-methoxypregna-3,5-dien-20-one is prepared from progesterone by methods well known in the art. The pregn-20-ones, such as 3-methoxypregna-3,5-dien-20-one, are oxidized with oxygen or air using a base catalyst in the presence of a phosphite reducing agent in a suitable solvent. The base catalyst consists of an alkali metal tert-alkoxide, which can be prepared from an alkali metal and a tert-alkanol. The oxidation reaction can be carried out at any temperature from about -20.degree. C. to about 50.degree. C. and for a period of 2-20 hours depending on the temperature at which the reaction is carried out. For example, at ambient temperature the rate of oxidation is sufficiently fast to complete the oxidation in 2 to 4 hours. This method for preparing 17.alpha.-hydroxy-20-ketosteroids from 20-ketosteroids is an important and valuable step in preparing corticosteroids and other hormones.
摘要翻译：根据本发明，通过氧化20-酮甾体如3-甲氧基 - 孕甾-3,5-二烯-20-酮制备17α-羟基-20-酮类固醇。 3-甲氧基孕甾-3,5-二烯-20-酮通过本领域熟知的方法由孕酮制备。在合适的溶剂中，在亚磷酸盐还原剂存在下，使用碱催化剂，用氧或空气氧化妊娠-20-酮，例如3-甲氧基孕烯-3,5-二烯-20-酮。碱催化剂由可由碱金属和叔烷醇制备的碱金属叔醇盐组成。氧化反应可以在约-20℃至约50℃的任何温度下进行，并且持续2-20小时，这取决于进行反应的温度。例如，在环境温度下，氧化速度足够快以在2-4小时内完成氧化。这种从20酮类固醇制备17α-羟基-20-酮糖类的方法是制备皮质类固醇和其他激素的重要和有价值的步骤。

10. 发明授权

US4325878A Process for preparing 21-lower alkoxyoxalylprogesterones 失效
标题翻译：制备21-低级烷氧基草酰孕酮的方法
公开(公告)号：US4325878A
公开(公告)日：1982-04-20
申请号：US239799
申请日：1981-03-02
申请人： Charles A. McCombs
发明人： Charles A. McCombs
IPC分类号： C07J9/00 , C07J51/00 , C07J7/00
CPC分类号： C07J9/00 , C07J51/00
摘要： In accordance with the present invention, 21-lower alkoxyoxalylprogesterone is prepared in high yield by the lower alkoxyoxalylation of 3-methoxypregna-3,5-diene-20-one. The 3-methoxypregna-3,5-diene-20-one is prepared from progesterone by methods well known in the art. The 3-methoxypregna-3,5-diene-20-one is lower alkoxyoxalylated with an alkoxide base and the corresponding lower alkyloxalate in a suitable solvent. The alkoxide base consists of a lower alkoxide with an alkali metal counter ion. The lower alkyl group of both the alkoxide and oxalate should be the same and also are the same as the group to be added to the 21 position of the 20-keto steroid, the lower alkyl group contains 1 to 6 carbon atoms. The lower alkoxyoxalylation reaction can be carried at any temperature below the boiling point of the solvent and for a period of 2-20 hours depending on the temperature at which the reaction is carried out. For example, at elevated temperatures the rate of reaction is sufficiently fast to complete the lower alkoxyoxalylation in 2 to 4 hours whereas if the reaction is carried out at ambient temperatures complete reaction can require 14 to 20 hours. The reaction is preferably carried out under an inert atmosphere such as a nitrogen or argon atmosphere.
摘要翻译：根据本发明，通过3-甲氧基孕甾-3,5-二烯-20-酮的较低的烷氧基化反应，以高产率制备了21-低级烷氧基草酰孕酮。 3-甲氧基孕甾-3,5-二烯-20-酮通过本领域熟知的方法由孕酮制备。 3-甲氧基嘧啶-3,5-二烯-20-酮在合适的溶剂中用烷氧基和低级烷基草酸酯进行低级烷氧基化。醇盐碱由具有碱金属抗衡离子的低级醇盐组成。醇盐和草酸盐的低级烷基应该是相同的，并且也与添加到20-酮类固醇的21位的基团相同，低级烷基含有1至6个碳原子。低级烷氧基酰化反应可以在低于溶剂沸点的任何温度下进行，并且取决于进行反应的温度，持续2-20小时。例如，在升高的温度下，反应速度足够快以在2至4小时内完成较低的烷氧基化反应，而如果反应在环境温度下进行，则完全反应可能需要14至20小时。反应优选在惰性气氛如氮气或氩气氛下进行。

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