公开(公告)号：US4524028A

公开(公告)日：1985-06-18

申请号：US423359

申请日：1982-09-24

Applicant: Jacques Gosteli ,  Ivan Ernest ,  Robert B. Woodward

Inventor： Jacques Gosteli ,  Ivan Ernest ,  Robert B. Woodward

IPC: C07D499/897 ,  C07D205/08 ,  C07D205/09 ,  C07D499/04 ,  C07D499/06 ,  C07D499/86 ,  C07D499/87 ,  C07D499/88 ,  C07F9/568 ,  C07D403/12 ,  C07D401/12 ,  C07D487/04

CPC classification number: C07F9/5683 ,  C07D205/09 ,  C07D499/88

Abstract: 2-Penem-3-carboxylic acid compounds of the formula ##STR1## in which R.sub.1 represents hydrogen, an organic radical bonded by a carbon atom to the ring carbon atom or an etherified mercapto group andR.sub.2 represents hydroxy or a radical R.sub.2.sup.A forming together with the carbonyl grouping --C(.dbd.O)-- a protected carboxyl group,1-oxides thereof, as well as salts of such compounds having salt-forming groups, in racemic and optically active form, processes for their preparation, pharmaceutical compositions containing such compounds, and their use as antibiotics, and intermediates and their processes which are useful in the production of the compounds of the formula I.

Abstract translation: 其中R 1表示氢，通过碳原子键合到环碳原子上的有机基团或醚化的巯基，R 2表示羟基或基团R 2 A的2-蒎烯-3-羧酸化合物 与羰基-C（= O） - 被保护的羧基，其1-氧化物以及具有成盐基团的化合物的盐以外消旋和旋光形式一起形成，其制备方法，药物组合物 含有这些化合物及其作为抗生素的用途，以及可用于制备式I化合物的中间体及其方法。

公开(公告)号：US4447360A

公开(公告)日：1984-05-08

申请号：US214316

申请日：1980-12-08

Applicant: Jacques Gosteli ,  Ivan Ernest ,  Robert B. Woodward

Inventor： Jacques Gosteli ,  Ivan Ernest ,  Robert B. Woodward

IPC: C07D499/897 ,  C07D205/08 ,  C07D205/09 ,  C07D499/04 ,  C07D499/06 ,  C07D499/86 ,  C07D499/87 ,  C07D499/88 ,  C07F9/568 ,  C07D401/12 ,  C07D405/12 ,  C07D409/12

CPC classification number: C07F9/5683 ,  C07D205/09 ,  C07D499/88

Abstract: 2-Penem-3-carboxylic acid compounds of the formula ##STR1## in which R.sub.1 represents hydrogen, an organic radical bonded by a carbon atom to the ring carbon atom or an etherified mercapto group andR.sub.2 represents hydroxy or a radical R.sub.2.sup.A forming together with the carbonyl grouping --C(.dbd.O)-- a protected carboxyl group,1-oxides thereof, as well as salts of such compounds having salt-forming groups, in racemic and optically active form, processes for their preparation, pharmaceutical compositions containing such compounds, and their use as antibiotics, and intermediates and their processes which are useful in the production of the compounds of the formula I.

Abstract translation: 其中R 1表示氢，通过碳原子键合到环碳原子上的有机基团或醚化的巯基，R 2表示羟基或基团R 2 A的2-蒎烯-3-羧酸化合物 与羰基-C（= O） - 被保护的羧基，其1-氧化物以及具有成盐基团的化合物的盐以外消旋和旋光形式一起形成，其制备方法，药物组合物 含有这些化合物及其作为抗生素的用途，以及可用于制备式I化合物的中间体及其方法。

公开(公告)号：US4364865A

公开(公告)日：1982-12-21

申请号：US158430

申请日：1980-06-11

Applicant: Ivan Ernest ,  Jacques Gosteli ,  Robert B. Woodward

Inventor： Ivan Ernest ,  Jacques Gosteli ,  Robert B. Woodward

IPC: C07D205/095 ,  C07D499/88 ,  C07F9/568 ,  C07D205/08

CPC classification number: C07D205/095 ,  C07D499/88 ,  C07F9/5683 ,  Y02P20/55

Abstract: The invention relates to 6-amino-2-penem-3-carboxylic acid compounds of the formula ##STR1## in which R.sub.1.sup.a denotes hydrogen or an amino protective group R.sub.1.sup.A and R.sub.1.sup.b represents hydrogen or an acyl radical Ac, or in which R.sub.1.sup.a and R.sub.1.sup.b conjointly form a bivalent amino protective group, R.sub.2 denotes hydroxyl or a radical R.sub.2.sup.A which, together with the carbonyl grouping --C(.dbd.O)--, forms a protected carboxyl group, and R.sub.3 represents hydrogen or an organic radical which is linked via a carbon atom to the ring carbon atom, and 1-oxides thereof, as well as salts of such compounds having salt-forming groups, which compounds possess antibiotic properties, processes for the manufacture of such compounds, and also pharmaceutical formulations containing compounds of the formula I with pharmacological properties, and the use thereof, either as antibiotics, preferably in the form of pharmaceutical formulations, or as intermediate products.

Abstract translation: 本发明涉及式（I）的6-氨基-2-青霉烯-3-羧酸化合物，其中R 1a表示氢或氨基保护基R 1A和R 1b表示氢或酰基Ac，或其中 R1a和R1b共同形成二价氨基保护基，R2表示羟基或基团R2A，其与羰基-C（= O） - 一起形成被保护的羧基，R 3表示氢或连接的有机基团 通过碳原子与环碳原子及其1-氧化物，以及具有成盐基团的化合物的盐，该化合物具有抗生素性质，制备这些化合物的方法，以及含有化合物的化合物的药物制剂 具有药理学性质的式I及其用途，优选为药物制剂形式的抗生素或作为中间产物。

公开(公告)号：US4165268A

公开(公告)日：1979-08-21

申请号：US846876

申请日：1977-10-31

Applicant: Franz Marti ,  Tibor Somlo ,  Jacques Gosteli

Inventor： Franz Marti ,  Tibor Somlo ,  Jacques Gosteli

IPC: C07B39/00 ,  C07C17/14 ,  C07C205/11 ,  C07C121/52

CPC classification number: C07C205/11 ,  C07B39/00 ,  C07C17/14

Abstract: A process for the production of benzal bromides which contain an electrophilic substituent in the ortho- and/or para-position of the formula (Ia), or of mixtures thereof with the corresponding benzyl bromides of the formula (Ib), ##STR1## IN WHICH R represents an electrophilic substituent in the ortho- and/or para position, by treating correspondingly substituted toluenes with elementary bromine under irradiation with visible light in a two-phase system which consists of an aqueous and an organic phase, which process comprises carrying out the reaction in the presence of a base.

Abstract translation: 制备在式（Ia）的邻位和/或对位含有亲电子取代基的苄基溴的方法，或其与式（Ib）的相应的苄基溴，（IMA） （Ib）其中R表示邻位和/或对位的亲电子取代基，通过在两相体系中用可见光照射下用基本溴处理相应的取代的甲苯，该两相体系由水和 有机相，该方法包括在碱的存在下进行反应。

公开(公告)号：US4020098A

公开(公告)日：1977-04-26

申请号：US594412

申请日：1975-07-09

Applicant: Jacques Gosteli

Inventor： Jacques Gosteli

IPC: C07C37/50 ,  C07C39/08 ,  C07C69/76

CPC classification number: C07C37/50 ,  C07C67/343 ,  C07C69/88 ,  C07C69/94

Abstract: According to the present invention, 5-substituted resorcinols of the formula I ##STR1## wherein R.sub.1 represents a hydrocarbon radical, optionally unsubstituted or substituted by inert substituents, are prepared by reacting a carboxylic acid ester of the formula IIr.sub.1 -- c .tbd. c -- co -- o -- r.sub.2 (ii)wherein R.sub.2 represents a non-aromatically bound lower hydrocarbon radical, in the presence of an alkaline condensation agent, with a diester of 3-oxoglutaric acid of the formula IIIr.sub.3 --o--co--ch.sub.2 --co--ch.sub.2 --co--o--r.sub.4 (iii)wherein R.sub.3 and R.sub.4 represent non-aromatically bound lower hydrocarbon radicals; hydrolyzing the resulting dihydroxyisophthalic acid acid ester of the formula IV ##STR2## and decarboxylating the hydrolyzed product, a specific embodiment is the preparation of 5-pentylresorcinol.

Abstract translation: 根据本发明，式I的5-取代间苯二酚（I）其中R 1表示任选未取代或被惰性取代基取代的烃基，其通过使式II的羧酸酯R 1 -C 其中R 2表示非芳香结合的低级烃基，在碱性缩合剂的存在下，与式III的3-氧代戊二酸的二酯R 3 -O-CO- CH2-CO-CH2-CO-O-R4（Ⅲ）其中R3和R4代表非芳香结合的低级烃基; 水解所得的式IV（IV）的二羟基间苯二酸酸酯并使水解产物脱羧，具体实施方案是5-戊基间苯二酚的制备。

公开(公告)号：US5536841A

公开(公告)日：1996-07-16

申请号：US492444

申请日：1995-06-19

Applicant: Gareth Griffiths ,  Rene Imwinkelried ,  Jacques Gosteli

Inventor： Gareth Griffiths ,  Rene Imwinkelried ,  Jacques Gosteli

IPC: C07D233/68 ,  C07D233/70 ,  C07D233/96 ,  C07D233/32

CPC classification number: C07D233/96 ,  C07D233/68

Abstract: A process for preparing 2-substituted 5-chloroimidazole-4-carbaldehydes of the general formula: ##STR1## In the process, a glycine ester hydrohalide is ring-closed with an imidate ester to obtain the intermediate 2-substituted 3,5-dihydroimidazol-4-one. This intermediate is converted with an N,N-substituted formamide acetel into an N,N-substituted aminomethyleneimidazolinone. This latter intermediate is chlorinated with phosphorus oxychloride or phosgene to obtain the final product 2-substituted 5-chlorimidazole-4-carbaldehydes of the general formula I.Also disclosed are N,N-substituted aminomethyleneimidazolinones of the general formula: ##STR2## wherein R is hydrogen or is an alkyl group, an alkenyl group, a cycloalkyl group, an arylalkyl group or an aryl group, and R.sub.5 and R.sub.6 are identical or different and each is an alkyl group or an aryl group, in the form of the E- or Z-isomer.

Abstract translation: 制备以下通式的2-取代的5-氯咪唑-4-甲醛的方法：在该方法中，甘氨酸酯氢卤化物与亚氨酸酯酯闭环，得到中间体2-取代的3,5-二 二氢咪唑-4-酮。 该中间体用N，N-取代的甲酰胺乙缩醛转化成N，N-取代的氨基亚甲基咪唑啉酮。 将后一中间体用磷酰氯或光气氯化，得到通式I的最终产物2-取代的5-氯咪唑-4-甲醛。还公开了通式如下的N，N-取代的氨基亚甲基咪唑啉酮其中 R是氢或是烷基，烯基，环烷基，芳基烷基或芳基，R 5和R 6相同或不同，各自为烷基或芳基，其形式为E - 或Z-异构体。

公开(公告)号：US5486617A

公开(公告)日：1996-01-23

申请号：US340377

申请日：1994-11-14

Applicant: Gareth Griffiths ,  Rene Imwinkelried ,  Jacques Gosteli

Inventor： Gareth Griffiths ,  Rene Imwinkelried ,  Jacques Gosteli

IPC: C07D233/68 ,  C07D233/70 ,  C07D233/96

CPC classification number: C07D233/96 ,  C07D233/68

Abstract: A process for preparing 2-substituted 5-chloroimidazole-4-carbaldehydes of the general formula: ##STR1## In the process, a glycine ester hydrohalide is ring-closed with an imidate ester to obtain the intermediate 2-substituted 3,5-dihydroimidazol-4-one. This intermediate is converted with an N,N-substituted formamide acetal into an N,N-substituted aminomethyleneimidazolinone. This latter intermediate is chlorinated with phosphorus oxychloride or phosgene to obtain the final product 2-substituted 5-chlorimidazole-4-carbaldehydes of the general formula I.Also disclosed are N,N-substituted aminomethyleneimidazolinones of the general formula: ##STR2## wherein R is hydrogen or is an alkyl group, an alkenyl group, a cycloalkyl group, an arylalkyl group or an aryl group, and R.sub.5 and R.sub.6 are identical or different and each is an alkyl group or an aryl group, in the form of the E- or Z-isomer.

Abstract translation: 制备以下通式的2-取代的5-氯咪唑-4-甲醛的方法：在该方法中，甘氨酸酯氢卤化物与亚氨酸酯酯闭环，得到中间体2-取代的3,5-二 二氢咪唑-4-酮。 该中间体用N，N-取代的甲酰胺缩醛转化成N，N-取代的氨基亚甲基咪唑啉酮。 将后一中间体用磷酰氯或光气氯化，得到通式I的最终产物2-取代的5-氯咪唑-4-甲醛。还公开了通式如下的N，N-取代的氨基亚甲基咪唑啉酮其中 R是氢或是烷基，烯基，环烷基，芳基烷基或芳基，R 5和R 6相同或不同，各自是烷基或芳基，其形式为E - 或Z-异构体。

公开(公告)号：US4952690A

公开(公告)日：1990-08-28

申请号：US396783

申请日：1989-08-21

Applicant: Jacques Gosteli ,  Ivan Ernest ,  Marc Lang ,  Robert B. Woodward

Inventor： Jacques Gosteli ,  Ivan Ernest ,  Marc Lang ,  Robert B. Woodward

IPC: A61K31/397 ,  A61K31/43 ,  A61P31/04 ,  C07D205/08 ,  C07D205/09 ,  C07D417/12 ,  C07D499/04 ,  C07D499/06 ,  C07D499/86 ,  C07D499/861 ,  C07D499/87 ,  C07D499/88 ,  C07D499/881 ,  C07D499/883 ,  C07D499/887 ,  C07D499/897 ,  C07F9/568

CPC classification number: C07D499/88 ,  C07D205/08 ,  C07D205/09 ,  C07F9/5683

Abstract: The invention relates to azetidin-2-ones of the formula ##STR1## wherein R.sub.a represents hydroxy-lower alkyl, R.sub.1 represents hydrogen, an organic radical bonded by a carbon atom to the ring carbon atom or an etherified mercapto group, R.sub.2.sup.A together with the carbonyl group to which it is attached is a protected carboxyl group and Z' is oxygen, sulfhur or an optionally substituted methylidene group, functional groups in the radicals R.sub.a, R.sub.1 and Z' optionally being in protected form. The azetidinones are useful intermediates for the preparation of penem antibiotics.

公开(公告)号：US4692543A

公开(公告)日：1987-09-08

申请号：US832760

申请日：1986-02-25

Applicant: Leander Tenud ,  Jacques Gosteli

Inventor： Leander Tenud ,  Jacques Gosteli

IPC: C07C229/22 ,  C07B31/00 ,  C07B53/00 ,  C07B57/00 ,  C07C51/00 ,  C07C51/41 ,  C07C59/255 ,  C07C67/00 ,  C07C213/00 ,  C07C213/10 ,  C07C215/40 ,  C07C253/00 ,  C07C255/26 ,  C07C120/04 ,  C07C121/16

CPC classification number: C07C59/255

Abstract: Process for the production of optically-active di-[3-chloro-2-oxy-propyltrimethylammonium]-tartrate. Racemic 3-chloro-2-oxy-propyltrimethylammonium-chloride is converted by racemate resolution with CaCl.sub.2, for example, into the optically-active di-[3-chloro-2-oxy-propyltrimethylammonium]-tartrate. Such optically-active tartrate compound is dissociated into calcium tartrate and optically-active 3-chloro-2-oxy-propyltrimethylammonium-chloride, and the latter is converted with inorganic cyanides. From the product, the production of optically-active carnitine nitrile chloride can be achieved.

Abstract translation: 制备光学活性二 - [3-氯-2-羟基 - 丙基三甲基铵] - 酒石酸盐的方法。 外消旋3-氯-2-氧 - 丙基三甲基氯化铵通过外消旋体拆分与CaCl 2转化成例如光学活性的二 - [3-氯-2-氧 - 丙基三甲基铵] - 酒石酸盐。 这样的光学活性酒石酸盐化合物被解离为酒石酸钙和光学活性的3-氯-2-氧 - 丙基三甲基氯化铵，后者用无机氰化物转化。 从产品出发，可以实现光学活性肉碱氯化腈的生产。

公开(公告)号：US4515717A

公开(公告)日：1985-05-07

申请号：US423351

申请日：1982-09-24

Applicant: Jacques Gosteli ,  Ivan Ernest ,  Robert B. Woodward

Inventor： Jacques Gosteli ,  Ivan Ernest ,  Robert B. Woodward

IPC: C07D499/897 ,  C07D205/08 ,  C07D205/09 ,  C07D499/04 ,  C07D499/06 ,  C07D499/86 ,  C07D499/87 ,  C07D499/88 ,  C07F9/568 ,  C07D401/12 ,  C07D405/12 ,  C07D409/12

CPC classification number: C07F9/5683 ,  C07D205/09 ,  C07D499/88

Abstract: 2-Penem-3-carboxylic acid compounds of the formula ##STR1## in which R.sub.1 represents hydrogen, an organic radical bonded by a carbon atom to the ring carbon atom or an etherified mercapto group andR.sub.2 represents hydroxy or a radical R.sub.2.sup.A forming together with the carbonyl grouping --C(.dbd.O)-- a protected carboxyl group,1-oxides thereof, as well as salts of such compounds having salt-forming groups, in racemic and optically active form, processes for their preparation, pharmaceutical compositions containing such compounds, and their use as antibiotics, and intermediates and their processes which are useful in the production of the compounds of the formula I.

Abstract translation: 其中R 1表示氢，通过碳原子键合到环碳原子上的有机基团或醚化的巯基，R 2表示羟基或基团R 2 A的2-蒎烯-3-羧酸化合物 与羰基-C（= O） - 被保护的羧基，其1-氧化物以及具有成盐基团的化合物的盐以外消旋和旋光形式一起形成，其制备方法，药物组合物 含有这些化合物及其作为抗生素的用途，以及可用于制备式I化合物的中间体及其方法。