公开(公告)号：US4333880A

公开(公告)日：1982-06-08

申请号：US228177

申请日：1981-01-26

申请人： Wolfgang Preuss ,  Michael Bahn ,  Rolf Schmid ,  Rudiger Wagner

发明人： Wolfgang Preuss ,  Michael Bahn ,  Rolf Schmid ,  Rudiger Wagner

IPC分类号： C12P33/16 ,  C07J9/00 ,  C07J13/00

CPC分类号： C07J13/007 ,  C07J9/005

摘要： A .DELTA..sup.1,4,17 -BNC compound having the formula: ##STR1## wherein X is a substituent selected from the group consisting of OH and OCH.sub.3 ; as well as its process of production by microbiological side-chain splitting of a 17-C-side-chain steroid with a defect mutant microorganism which gives a steroid with a 17-C-.alpha.-propionic acid substituent in the absence of inhibitors inhibiting either the cleavage of the steroid ring or microorganism growth, where the defect mutant microorganisms are grown under a reduced air supply whereby an enrichment of .DELTA..sup.1,4,17 -BNC occurs.

摘要翻译： 具有下式的DELTA 1,4,17-BNC化合物：其中X是选自OH和OCH 3的取代基; 以及其通过17-C-侧链类固醇与缺失突变体微生物的微生物侧链裂解的生产过程，所述缺陷突变体微生物在不存在抑制剂的情况下给予具有17-C-α-丙酸取代基的类固醇 类固醇环或微生物生长的切割，其中缺陷突变体微生物在减少的空气供应下生长，从而发生DELTA 1,4,17-BNC的富集。

公开(公告)号：US4432905A

公开(公告)日：1984-02-21

申请号：US391841

申请日：1982-06-24

申请人： Michael Bahn ,  Wolfgang Preuss ,  Rolf Schmid ,  Rudiger Wagner

发明人： Michael Bahn ,  Wolfgang Preuss ,  Rolf Schmid ,  Rudiger Wagner

IPC分类号： C07J7/00 ,  C07J9/00 ,  C07J13/00 ,  C07J41/00 ,  C12P33/08

CPC分类号： C12P33/08 ,  C07J13/007 ,  C07J41/005 ,  C07J41/0088 ,  C07J7/0005 ,  C07J7/002 ,  C07J7/007 ,  C07J9/005

摘要： The degradation of steroid-C22-carboxylic acids to the C20-carbonyl steroids is carried out in simplified form and preferably without isolating intermediate reaction products by using 17(20)-steroid-22-carboxylic acids as starting material and directly transforming them into the 20-carbonyl compound through their respective acid halides by the Curtius degradation or by carboxy-inversion degradation. The acetyl substituent thus formed in C17 of the steroid compounds is present in the pharmacologically required configuration.

摘要翻译： 类固醇-C22-羧酸对C20-羰基类固醇的降解以简化的形式进行，优选不用分离中间体反应产物，通过使用17（20） - 类固醇22-羧酸作为起始原料并将其直接转化为 20-羰基化合物通过它们各自的酰卤通过Curtius降解或羧基反转降解。 因此在类固醇化合物的C17中形成的乙酰基取代基以药理学上需要的形式存在。

公开(公告)号：US4362815A

公开(公告)日：1982-12-07

申请号：US128223

申请日：1980-03-07

申请人： Frank F. Hill ,  Joachim Schindler ,  Rolf Schmid ,  Wolfgang Preuss ,  Alfred Struve

发明人： Frank F. Hill ,  Joachim Schindler ,  Rolf Schmid ,  Wolfgang Preuss ,  Alfred Struve

IPC分类号： C12N15/00 ,  C07J9/00 ,  C12N1/20 ,  C12N15/01 ,  C12P33/00 ,  C12P33/16 ,  C12R1/15

CPC分类号： C12N15/01 ,  C07J9/005 ,  C12P33/005

摘要： For the production of 17-C-steroid-.alpha.-propionic acid compounds by microbial side chain degradation on 17-C-side chain steroid substrates wild strain microorganisms selected in predetermined manner are subjected to a multi-stage mutation and selection. The resultant mutant strains are capable of supplying the desired compounds, e.g. .DELTA.-4 BNC and/or .DELTA.-1,4 BNC in high yields even in the absence of inhibitors arresting the growth and/or degradation of the steroid ring. Wild strains and mutants particularly suitable, and their choice, production and use, are described.

摘要翻译： 为了通过在17-C侧链类固醇底物上的微生物侧链降解生产17-C-类固醇-α-丙酸化合物，以预定方式选择的野生菌株微生物进行多阶段突变和选择。 所得到的突变菌株能够提供所需化合物，例如 即使在没有阻止类固醇环的生长和/或降解的抑制剂的情况下，也能以高产率产生DELTA-4BNC和/或DELTA-1,4BNC。 描述了特别适合的野生株和突变体及其选择，生产和使用。

公开(公告)号：US4320195A

公开(公告)日：1982-03-16

申请号：US29415

申请日：1979-04-12

申请人： Frank Hill ,  Wolfgang Preuss ,  Joachim Schindler ,  Rolf Schmid ,  Alfred Struve

发明人： Frank Hill ,  Wolfgang Preuss ,  Joachim Schindler ,  Rolf Schmid ,  Alfred Struve

IPC分类号： C12N1/20 ,  C07J9/00 ,  C12N1/00 ,  C12N1/02 ,  C12N15/00 ,  C12N15/01 ,  C12P33/00 ,  C12P33/16 ,  C12R1/025 ,  C12R1/06 ,  C12R1/07 ,  C12R1/13 ,  C12R1/15 ,  C12R1/20 ,  C12R1/32 ,  C12R1/365 ,  C12R1/425 ,  C12R1/465

CPC分类号： C07J9/005 ,  C12N15/01 ,  C12P33/005 ,  Y10S435/843

摘要： A process for the production of useful steroids obtained by side chain degradation of sterol source materials through the use of microorganisms is described.

摘要翻译： 描述了通过使用微生物通过侧链降解固醇源材料获得的有用类固醇的生产方法。

公开(公告)号：US4430270A

公开(公告)日：1984-02-07

申请号：US407791

申请日：1982-08-13

申请人： Wolfgang Preuss

发明人： Wolfgang Preuss

IPC分类号： C07J9/00 ,  C07J41/00 ,  C07J1/00

CPC分类号： C07J9/005 ,  C07J41/005 ,  C07J41/0088

摘要： C21-steroid compounds with a nitrogen function in the 20-position corresponding to general formula I below ##STR1## in which Y is hydrogen, a hydroxyl group or, together with the C-atom substituted by Y, represents a carbonyl group or may even be replaced by a 9(11)-ene bond and in which X is hydrogen, acyl, a carbonic acid ester residue or, together with the adjacent hydrogen atom on the nitrogen, represents a carbonyl group, may be obtained by converting the steroid-C20-carboxylic acid halides structurally analogous to the required reaction product into the corresponding carboxylic acid azide and either transforming the carboxylic acid azide thus formed into the C20-isocyanate through the elimination of nitrogen and, if desired, converting the C20-isocyanate thus obtained into the C20-carbamate and/or the C20-amine or directly transforming the carboxylic acid azide into the C20-amine. The compounds thus produced corresponding to general formula I, in which Y represents an oxygen function or in which the substituent Y is replaced by a 9(11)-ene bond, are new. The 20 amino compounds are readily converted to progesterone and other useful steroids.

摘要翻译： 其中Y为氢，羟基或与Y取代的C原子一起形成对应于下文通式I的通式I的20位上具有氮官能团的C21-类固醇化合物代表羰基 或者甚至可以被9（11） - 烯键取代，其中X是氢，酰基，碳酸酯残基，或者与氮上的相邻氢原子一起代表羰基，可以通过转化 类固醇-C20-羧酸卤化物在结构上类似于所需的反应产物进入相应的羧酸叠氮化物，并且通过消除氮而将所形成的羧酸叠氮化物转化为C20异氰酸酯，如果需要，转化C20异氰酸酯 从而得到C 20 - 氨基甲酸酯和/或C20-胺，或直接将羧酸叠氮化物转化为C20-胺。 对应于通式I，其中Y表示氧官能团或其中取代基Y被9（11） - 烯键取代的化合物是新的。 20个氨基化合物很容易转化成孕激素和其他有用的类固醇。

公开(公告)号：US20050241407A1

公开(公告)日：2005-11-03

申请号：US11115393

申请日：2005-04-27

申请人： Remy Kirchdoerffer ,  Gerd Ebelt ,  Wolfgang Preuss

发明人： Remy Kirchdoerffer ,  Gerd Ebelt ,  Wolfgang Preuss

IPC分类号： G01B11/30 ,  G01L1/16 ,  G01L1/22 ,  G01L5/00 ,  G01N3/08

CPC分类号： G01L1/2231 ,  G01L5/0085

摘要： The invention relates to a measuring device, comprising a housing having two opposing measuring surfaces, to each of which there are assigned a phototransmitter and photoreceiver disposed in the interior of said housing, each measuring surface having an opening which is transparent to light of at least one wavelength and at least one of the two measuring surfaces is in the form of a dynamometer.

摘要翻译： 本发明涉及一种测量装置，包括具有两个相对的测量表面的壳体，每个测量表面分配有设置在所述壳体内部的光发送器和光接收器，每个测量表面具有至少对于至少透光的开口 一个波长，并且两个测量表面中的至少一个是测力计的形式。

公开(公告)号：US4370271A

公开(公告)日：1983-01-25

申请号：US262969

申请日：1981-05-12

申请人： Wolfgang Preuss

发明人： Wolfgang Preuss

IPC分类号： C07J13/00 ,  C07J5/00

CPC分类号： C07J13/007

摘要： A process for the partial reduction of C21-steroid carboxylic acids and their esters to C21-steroid alcohols and new C21-steroid alcohols.DELTA.4,17(20)-C21-steroid carboxylic acids optionally containing further double bonds in the 1- and/or 9(11)-position and their esters corresponding to general formula I below ##STR1## in which R represents hydrogen or a hydrocarbon radical and A represents hydrogen, hydroxyl or, together with the C-atom substituted by A, a carbonyl group and in which, finally, the substituent A may even be replaced by an additional olefinic double bond in the 9(11)-position, are reacted with diisobutyl aluminium hydride without the A-ring in the steroid skeleton being blocked in such quantities that all the oxygen-containing functional groups are reduced to the hydroxyl group. The aluminium-containing intermediate reaction product is then subjected to the selective Oppenauer oxidation to form the 3-keto compound. The 3-oxo-C21-steroid alcohols may be obtained in high yields in this way. The process is suitable for the preparation of pharmacologically active steroid compounds having the 17,21-diol-20-one configuration. It enables the new compuonds, pregna-1,4,17(20)-triene-3-one-21-ol and pregna-1,4,9(11),17(20)-tetraene-3-one-21-ol and their 21-acetoxy compounds, to be obtained.

摘要翻译： 将C21-类固醇羧酸及其酯部分还原为C21-类固醇和新的C21-类固醇醇DELTA 4,17（20）-C21-类固醇羧酸的方法，其任选地含有1-和/ 或9（11） - 位和其对应于下式（I）的通式I的酯，其中R表示氢或烃基，A表示氢，羟基或与A取代的C原子一起形成 羰基，其中最后，取代基A甚至可以被9（11）位中的另外的烯属双键替代，与类似甾体骨架中没有A环的二异丁基铝氢化物反应， 所有含氧官能团都被还原为羟基。 然后将含铝中间体反应产物进行选择性的Oppenauer氧化以形成3-酮化合物。 以这种方式可以高产率获得3-氧代C21-类固醇。 该方法适用于制备具有17,21-二醇-20-一构型的药理活性类固醇化合物。 它使得新的化合物，前 - 1,4,17（20） - 三烯-3-酮-21-醇和前 - 1,4,9（11），17（20） - 四烯-3-酮-21 - 醇及其21-乙酰氧基化合物。

公开(公告)号：US07249522B2

公开(公告)日：2007-07-31

申请号：US11115393

申请日：2005-04-27

申请人： Rémy Kirchdoerffer ,  Gerd Ebelt ,  Wolfgang Preuss

发明人： Rémy Kirchdoerffer ,  Gerd Ebelt ,  Wolfgang Preuss

IPC分类号： G01N3/08

CPC分类号： G01L1/2231 ,  G01L5/0085

摘要： The invention relates to a measuring device, comprising a housing having two opposing measuring surfaces, to each of which there are assigned a phototransmitter and photoreceiver disposed in the interior of said housing, each measuring surface having an opening which is transparent to light of at least one wavelength and at least one of the two measuring surfaces is in the form of a dynamometer.

摘要翻译： 本发明涉及一种测量装置，包括具有两个相对的测量表面的壳体，每个测量表面分配有设置在所述壳体内部的光发送器和光接收器，每个测量表面具有至少对于至少透光的开口 一个波长，并且两个测量表面中的至少一个是测力计的形式。

公开(公告)号：US4446072A

公开(公告)日：1984-05-01

申请号：US407751

申请日：1982-08-13

申请人： Wolfgang Preuss

发明人： Wolfgang Preuss

IPC分类号： C07J7/00 ,  C07J9/00 ,  C07J5/00

CPC分类号： C07J7/0005 ,  C07J7/007 ,  C07J9/005

摘要： .DELTA.4-Steroid-20-carboxylic acids (BNC compounds) which may optionally contain at least one other double bond in the 1(2)- and/or 9(11)-position and which may also contain an oxygen function, particularly a hydroxyl group or a keto group, in the 11-position, are degraded in the 20-carboxyl group by carboxy inversion degradation. To achieve this, the BNC-carboxylic acids are first transformed into their acid halides which are reacted with peracids to form mixed acid anhydrides, followed by hydrolysis. The reaction product obtained is a mixture of 20-hydroxy- and 20(21)-ene-steroid compounds which contain one carbon atom less than the starting material used. New and known C21-steroid compounds can be produced by the process. The C21-steroid compounds having an oxygenated function in the 11-position may be processed to prednisolone and prednisone by known procedures.

摘要翻译： DELTA 4-类固醇-20-羧酸（BNC化合物），其可以任选地在1（2） - 和/或9（11） - 位中含有至少一个其他双键，并且还可以含有氧功能，特别是 羟基或酮基在11位上通过羧基反转降解在20-羧基中降解。 为了实现这一点，首先将BNC-羧酸转化成它们的酰基卤，其与过酸反应形成混合酸酐，然后进行水解。 获得的反应产物是含有比所用起始物少一个碳原子的20-羟基和20（21） - 烯类固醇化合物的混合物。 新的和已知的C21-类固醇化合物可以通过该方法生产。 具有11位氧合功能的C21类固醇化合物可以通过已知方法加工成泼尼松龙和泼尼松。

公开(公告)号：US4519949A

公开(公告)日：1985-05-28

申请号：US423276

申请日：1982-09-24

申请人： Wolfgang Preuss

发明人： Wolfgang Preuss

IPC分类号： C07J9/00 ,  C07J13/00 ,  C07J41/00

CPC分类号： C07J13/007 ,  C07J41/0061 ,  C07J9/005

摘要： New .DELTA.1,4,9(11)-pregnatrien-3-one-2o-carboxlic acid compounds are described, corresponding to general formula I below: ##STR1## in which X represents halogen, particularly chlorine or bromine or NH.sub.2. There is also described the process for producing compounds corresponding to general formula I by dehydrating the corresponding saturated starting compounds hydroxylated in the 11-position to form the 9(11)-ene-bond, after which the product obtained is, if desired, subjected to chemical transformation into the end products corresponding to general formula I. In particular, it is possible to carry out formation of the 20-acid halides and dehydration in the 9(11)-position in a single process step.

摘要翻译： 描述了对应于以下通式I的新型DELTA 1,4,9（11） - 孕三烯-3-酮-20-羧酸化合物：其中X表示卤素，特别是氯或溴或NH 2 。 还描述了通过将在11位羟基化的相应的饱和起始化合物脱水以形成9（11） - 烯键来制备相应于通式I的化合物的方法，然后如果需要，所得产物是 化学转化成与通式I相应的最终产物。特别地，可以在单一工艺步骤中在9（11） - 位中进行20-酰卤的形成和脱水。