公开(公告)号：US4491659A

公开(公告)日：1985-01-01

申请号：US498447

申请日：1983-05-26

申请人： Philippe L. Durette

发明人： Philippe L. Durette

IPC分类号： C07D309/30 ,  C07H7/033 ,  C07H15/04 ,  C07H5/06

CPC分类号： C07H15/04 ,  C07D309/30 ,  C07H7/033 ,  Y02P20/55

摘要： Disclosed is a chiral, total synthesis of thienamycin from D-glucose which proceeds via intermediates I, II, III and IV to known lactone V which is known to be useful via acid VI in the total synthesis of thienamycin (VII): ##STR1## wherein R.sup.1 is hydrogen or a removable protecting group; R is a removable protecting group.

摘要翻译： 公开了从中间体I，II，III和IV经过中间体I，II，III和IV进行的已知可在Thienamycin（VII）的全合成中已知可用于VI的已知内酯V的D-葡萄糖的手性全合成： 其中R1是氢或可除去的保护基团;其中R1是氢或可除去的保护基团; R是可除去的保护基团。

公开(公告)号：US4384998A

公开(公告)日：1983-05-24

申请号：US248177

申请日：1981-03-30

申请人： Philippe L. Durette

发明人： Philippe L. Durette

IPC分类号： C07D205/08 ,  C07D477/04 ,  C07H9/00 ,  C07H19/04 ,  C07D487/04

CPC分类号： C07H19/04 ,  C07D205/08 ,  C07D477/04 ,  C07H9/00 ,  Y02P20/55

摘要： Disclosed is a chiral, total synthesis of thienamycin from D-glucose which proceeds via intermediates I, II and III to known aldehyde IV which is known to be useful in the total synthesis of thienamycin (V): ##STR1## wherein: R is lower alkyl having 1-6 carbon atoms or bi-valent alkyl having 2-6 carbon atoms which joins the two sulfur atoms; R.sup.1 is lower alkyl or aralkyl, such as benzyl and the like; and R.sup.2 is hydrogen or a removable protecting group, such as triorganosilyl wherein the organo groups are independently selected from lower alkyl, phenyl and phenylloweralkyl.

摘要翻译： 公开了从D-葡萄糖的手性全合成，其通过中间体I，II和III进行已知的醛IV，其已知可用于噻吗化合物（V）的全合成： 其中：R是具有1-6个碳原子的低级烷基或连接两个硫原子的具有2-6个碳原子的二价烷基; R1是低级烷基或芳烷基，例如苄基等; 并且R 2是氢或可除去的保护基团，例如三有机甲硅烷基，其中有机基团独立地选自低级烷基，苯基和苯基低级烷基。

公开(公告)号：US4315913A

公开(公告)日：1982-02-16

申请号：US157906

申请日：1980-06-09

申请人： Philippe L. Durette

发明人： Philippe L. Durette

IPC分类号： A61K39/39 ,  A61P31/04 ,  C07D309/14 ,  C07K9/00 ,  A61K39/00 ,  A61K37/02 ,  C07C103/52

CPC分类号： C07K9/005 ,  C07D309/14

摘要： Immunologically active compounds of the formula: ##STR1## wherein R.sub.1 is C.sub.1-7 alkyl, substituted C.sub.1-7 alkyl; phenyl; or substituted phenyl;R.sub.2 is hydrogen; or C.sub.1-10 alkyl;R.sub.3 and R.sub.4 may be the same or different and are each independently hydrogen or acyl of the formula: ##STR2## where X is --O--, --S--, --CH.sub.2 --, or ##STR3## R.sub.9, R.sub.10 and R.sub.12 may be the same or different and are each independently hydrogen; C.sub.1-20 alkyl; C.sub.2-20 alkenyl; C.sub.1-20 alkylcarbonyloxy; amino; phenyl; benzyl; C.sub.1-20 alkoxymethyl; or C.sub.1-20 alkylamido;R.sub.11 is hydrogen; C.sub.1-30 alkyl; C.sub.2-30 alkenyl; C.sub.1-30 alkoxy; phenyl; C.sub.1-20 alkylsulfonyl; or cholesteryl; andm is 0-90; and n is 0 or 1, provided that when n is 0, R.sub.11 may additionally be phenyl, substituted phenyl, 1-adamantyl, or heterocycle selected from the group consisting of 2- or 3-furyl, 2- or 3-thienyl, 2- or 3-pyrrolidinyl, 2-, 3-, or 4-pyridyl, and 1-tetrazolyl, said heterocycle optionally substituted with C.sub.1-20 alkylcarbonyl;R.sub.5 is hydrogen; or R.sub.5 -R.sub.6 together is --CH.sub.2 --CH.sub.2 --CH.sub.2 ;R.sub.6 is hydrogen; C.sub.1-7 alkyl; hydroxymethyl; mercaptomethyl; benzyl; or substituted benzyl;R.sub.7 and R.sub.8 may be the same or different and are each independently COOR or CONR'R", where R is hydrogen or C.sub.1-7 alkyl, and R' and R" are each independently hydrogen or C.sub.1-3 alkyl;when R.sub.2 is C.sub.1-10 alkyl, the stereochemistry at asymmetric center I can be either D or L;when R.sub.6 is not hydrogen, the stereochemistry at asymmetric center II is L;the stereochemistry at asymmetric center III is D.

摘要翻译： 具有下式的免疫活性化合物：细胞壁的更好的（I）糖苷聚糖片段，更具体地，是胞壁酰二肽，即N-乙酰胞壁酰基-L-丙氨酰-D-异谷氨酰胺（MDP）。 向含有抗原的弗氏不完全佐剂（90％矿物油和10％Arlacel A）的乳液中加入合成的MDP可增加针对抗原的抗体水平（体液应答），诱导迟发性超敏反应（细胞免疫）。

公开(公告)号：US4256735A

公开(公告)日：1981-03-17

申请号：US7108

申请日：1979-01-29

申请人： Philippe L. Durette ,  Tsung-Ying Shen

发明人： Philippe L. Durette ,  Tsung-Ying Shen

IPC分类号： A61K39/39 ,  A61P31/04 ,  C07K1/113 ,  C07K9/00 ,  A61K37/00 ,  C07C103/52

CPC分类号： C07K9/005

摘要： 2-Amino-2-deoxy-glycoses of the general structural formula: ##STR1## wherein R.sub.1 is hydrogen, alkyl (1-7C), substituted alkyl (1-7C), phenyl, substituted phenyl, benzyl, or substituted benzyl;R.sub.2 is alkyl, substituted alkyl, phenyl, or substituted phenyl;R.sub.3 is H or lower alkyl (1-10C) with the proviso that when the aminoglycose has the 2-amino-2-deoxy-D-glucose configuration, R.sub.3 cannot be H;R.sub.4 and R.sub.5 are same or different and are H, aliphatic or aromatic acyl (2-21C) or substituted acyl (2-21C);R.sub.6 is H, or R.sub.6 -R.sub.7 together is --CH.sub.2 --CH.sub.2 --CH.sub.2 --,R.sub.7 is H, alkyl (1-7C), hydroxymethyl, mercaptomethyl, benzyl, or substituted benzyl;R.sub.8 and R.sub.9 each is carboxyl, esterified carboxyl (1-7C), amidated carboxyl, or mono- or di-alkyl-(1-3C)-amidated carboxyl;Provided that when R.sub.3 is lower alkyl, the stereochemistry at asymmetric center I can be either D or L, but that when the aminoglycose has the 2-amino-2-deoxy-D-glucose configuration, the stereochemistry at I cannot be D;When R.sub.7 is not H, the stereochemistry at asymmetric center II is either L or D; andThe stereochemistry at asymmetric center III is D.These compounds possess immunostimulatory properties.

摘要翻译： 2-氨基-2-脱氧糖苷，其通式为：其中R1为氢，烷基（1-7C），取代的烷基（1-7C），苯基，取代的苯基，苄基或取代的苄基; R2是烷基，取代的烷基，苯基或取代的苯基; R3是H或低级烷基（1-10C），条件是当氨基糖类具有2-氨基-2-脱氧-D-葡萄糖构型时，R3不能是H; R4和R5相同或不同，为H，脂族或芳族酰基（2-21C）或取代的酰基（2-21C）; R6是H或R6-R7一起是-CH 2 -CH 2 -CH 2 - ，R 7是H，烷基（1-7C），羟甲基，巯基甲基，苄基或取代的苄基; R8和R9各自为羧基，酯化羧基（1-7C），酰胺化羧基或单 - 或二 - 烷基 - （1-3C） - 酰胺化羧基; 假设当R3是低级烷基时，不对称中心I的立体化学可以是D或L，但是当氨基糖类具有2-氨基-2-脱氧-D-葡萄糖构型时，I的立体化学不能是D; 当R7不为H时，不对称中心II的立体化学为L或D; 而不对称中心III的立体化学是D.这些化合物具有免疫刺激性质。

公开(公告)号：US4228274A

公开(公告)日：1980-10-14

申请号：US922897

申请日：1978-07-10

申请人： Mitree M. Ponpipom ,  Robert L. Bugianesi ,  Philippe L. Durette ,  Howard M. Katzen ,  Tsung-Ying Shen

发明人： Mitree M. Ponpipom ,  Robert L. Bugianesi ,  Philippe L. Durette ,  Howard M. Katzen ,  Tsung-Ying Shen

IPC分类号： C07H13/04 ,  C07H15/04 ,  C07H15/14 ,  C07H5/06 ,  C07H5/08

CPC分类号： C07H13/04 ,  C07H15/04 ,  C07H15/14

摘要： The invention disclosed herein relates to novel 1-deoxy-glycopyranosides, preferably 1-deoxy-D-mannopyranosides, having in the 1-position of the pyranoside ring an .omega.-aminoalkylthio, .omega.-aminoalkyloxy or .omega.-aminoalkanoylamino substituent; and to novel processes for preparing these 1-substituted-1-deoxy-glycopyranosides starting with the corresponding tetra-O-acetyl-glycopyranosyl bromide or amine. These .omega.-amino(alkylthio, alkyloxy or alkanoylamino)-1-deoxy-glycopyranosides, and in particular 1-[(6'-aminohexyl)thio or oxy]-1-deoxy-D-mannopyranosides, possess insulin-like activity.

摘要翻译： 本文公开的本发明涉及在吡喃糖苷环的1位具有ω-氨基烷硫基，ω-氨基烷氧基或ω-氨基烷酰基氨基取代基的1-脱氧-D-甘露吡喃糖苷类的新型1-脱氧-D-吡喃甘露糖苷， 以及由相应的四-O-乙酰基 - 吡喃葡糖基溴或胺开始制备这些1-取代-1-脱氧 - 糖吡喃糖苷的新方法。 这些ω-氨基（烷硫基，烷氧基或烷酰氨基）-1-脱氧 - 糖吡喃糖苷，特别是1 - [（6'-氨基己基）硫代或氧基] -1-脱氧-D-甘露吡喃糖苷类，具有胰岛素样活性。