(1S,5R,6R,7R)-6-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octenyl]-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one | 1064596-51-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1S,5R,6R,7R)-6-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octenyl]-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one
• 英文别名: (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-[(1E,3S)-3-hydroxy-4-methyl-1-octenyl]-2H-cyclopenta[b]furan-2-one；[(3aR,4R,5R,6aS)-4-[(E,3S)-3-hydroxy-4-methyloct-1-enyl]-2-oxo-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-5-yl] benzoate
• CAS: 1064596-51-5
• 化学式: C₂₃H₃₀O₅
• 分子量: 386.488
• InChiKey: UYRWMBNSISOFAC-VXRHXURKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,5R,6R,7R)-6-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octenyl]-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one 、 叔丁基二苯基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 (3aR,4R,5R,6aS)-5-(benzoyloxy)-4-[(1E,3S)-3-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4-methyl-1-octenyl]hexahydro-2H-cyclopenta[b]furan-2-one
  参考文献：
  名称：

  Novel 5-cyano-prostacyclin derivatives as agents for the treatment of influenza a viral infection

  摘要：

  该发明涉及式(I)的化合物： 其中A、B、D、E、m和R1-R5如本文所述，可以是单一立体异构体或立体异构体混合物，或其药学上可接受的盐、包合物或前药。这些化合物可用于治疗与流感A病毒相关的呼吸道疾病，例如H5N1及其突变体。本发明还涉及包含所述化合物的药物组合物以及制备所述化合物的方法。

  公开号：

  US20080242714A1
• 作为产物：
  描述：

  2-乙基己酸甲酯 在 甲醇 、 sodium tetrahydroborate 、 正丁基锂 、 cerium(III) chloride 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 4.67h， 生成 (1S,5R,6R,7R)-6-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-octenyl]-7-benzoyloxy-2-oxabicyclo[3.3.0]octan-3-one 、 (3aR,4R,5R,6aS)-5-(benzoyloxy)hexahydro-4-[(1E,3R)-3-hydroxy-4-methyl-1-octenyl]-2H-cyclopenta[b]furan-2-one
  参考文献：
  名称：

  WO2008/116670

  摘要：

  公开号：

文献信息

• Novel 5-cyano-prostacyclin derivatives and their use as agents for the treatment of influenza a viral infection
  申请人：Bayer Schering Pharma Aktiengesellschaft

  公开号：EP1975163A1

  公开（公告）日：2008-10-01

  This invention is directed to compounds of formula (I): where A, B, D, E, m, and R1 - R5 are as described herein, as single stereoisomers or as mixtures of stereoisomers, or pharmaceutically acceptable salts, clathrates, or prodrugs thereof, which compounds are useful in treating respiratory diseases associated with influenza A viruses, such as for example H5N1 and its mutations. Pharmaceutical compositions comprising the compounds of the invention and methods of preparing the compounds of the invention are also disclosed.

  本发明涉及以下式(I)的化合物：其中A、B、D、E、m和R1 - R5如本文所述，可以是单个立体异构体或立体异构体混合物，或其药学上可接受的盐、包合物或前药，这些化合物在治疗与流感A病毒相关的呼吸道疾病方面有用，例如H5N1及其突变体。还公开了包含本发明化合物的药物组合物和制备本发明化合物的方法。
• Novel 5-cyano-prostacyclin derivatives as agents for the treatment of autoimmune diseases
  申请人：Guilford William

  公开号：US20080242713A1

  公开（公告）日：2008-10-02

  This invention is directed to compounds of formula (I): where A, B, D, E, m, and R 1 -R 5 are as described herein, as single stereoisomers or as mixtures of stereoisomers, or pharmaceutically acceptable salts, clathrates, or prodrugs thereof, which compounds are useful in treating autoimmune diseases. Pharmaceutical compositions comprising the compounds of the invention and methods of preparing the compounds of the invention are also disclosed.

  本发明涉及具有以下结构的化合物（I）：其中A、B、D、E、m和R1-R5如本文所述，可以是单一立体异构体或立体异构体混合物，或其药学上可接受的盐、包合物或前药，这些化合物可用于治疗自身免疫疾病。本发明还涉及包含所述化合物的药物组合物以及制备所述化合物的方法。
• Prostacyclins and use as medicinal agents
  申请人：Schering Aktiengesellschaft

  公开号：US04364951A1

  公开（公告）日：1982-12-21

  Prostane derivatives of the formula ##STR1## wherein B is straight-chain or branched alkylene of 1-10 carbon atoms, A is --CH.sub.2 --CH.sub.2 --, trans--CH.dbd.CH--, or --C.tbd.C--; W is hydroxymethylene or a ##STR2## wherein the OH-group can be in the .alpha.- or .beta.-position, and is optionally modified by replacement of the H atom with an ether or acyl group which is conventional for such replacements in prostaglandins and which is readily cleavable at physiological pH's; D and E together are a direct bond or D is straight-chain or branched alkylene of 1-10 carbon atoms, or, such an alkylene of 4-10 carbon atoms containing a double bond in the 2- or 3- position, all of which can optionally be substituted by fluorine, 1,2-methylene, 1,1-trimethylene, or methoxy; E is oxygen, sulfur, --C.tbd.C-- or a direct bond; R.sub.2 is C.sub.1-10, C.sub.2-10 alkenyl, each of which optionally is substituted phenyl, 1-naphthyl or 2-naphthyl, each of which is substituted as defined below; C.sub.4-10 cycloalkyl optionally substituted by C.sub.1-4 alkyl; phenyl, 1-naphthyl, or 2-naphthyl, each of which can optionally be substituted by 1-3 halogen atoms, a phenyl group, 1-3 alkyl groups each independently of 1-4 carbon atoms, or a chloromethyl, fluoromethyl, trifluoromethyl, carboxy, C.sub.1 -C.sub.4 -alkoxy, or hydroxy group, or an aromatic 5- or 6-membered heterocyclic ring having one hetero ring atom which is O, N, or S, the remaining atoms being carbon; and R.sub.1 is hydroxy optionally modified as for W above, have valuable vasodilating, anti-hypertensive, and bronchodilating pharmacological properties.

  公式为 ##STR1## 的proSTane衍生物，其中B是1-10个碳原子的直链或支链烷基，A是--CH.sub.2 --CH.sub.2 --，trans--CH.dbd.CH--或--C.tbd.C--；W是羟甲基或 ##STR2## 其中OH基团可以在α或β位置，且可以通过取代H原子以ether或acyl基团进行修改，这在proSTaglandins中是常规的，并且在生理pH下容易被裂解；D和E一起是直接键，或者D是1-10个碳原子的直链或支链烷基，或者是含有2-或3-位置双键的4-10个碳原子的烷基，所有这些都可以选择性地被氟、1,2-亚甲基、1,1-三亚甲基或甲氧基取代；E是氧、硫、--C.tbd.C--或直接键；R.sub.2是C.sub.1-10、C.sub.2-10烯基，每个烯基可以选择性地被取代为苯基、1-萘基或2-萘基，每个取代如下所定义；C.sub.4-10环烷基可以选择性地被C.sub.1-4烷基取代；苯基、1-萘基或2-萘基，每个可以选择性地被1-3个卤素原子、苯基、1-3个独立的碳原子为1-4的烷基取代，或者是氯甲基、氟甲基、三氟甲基、羧基、C.sub.1-C.sub.4-烷氧基或羟基，或者是具有一个杂环原子的芳香5-或6-成员环，该杂环原子是O、N或S，其余原子是碳；R.sub.1是羟基，可以选择性地按照上述W进行修改，具有有价值的扩血管、降压和支气管扩张药理学特性。
• 5-cyano-prostacyclin derivatives as agents for the treatment of influenza a viral infection
  申请人：Bayer Schering Pharma Aktiengesellschaft

  公开号：US07776896B2

  公开（公告）日：2010-08-17

  This invention is directed to compounds of formula (I): where A, B, D, E, m, and R1-R5 are as described herein, as single stereoisomers or as mixtures of stereoisomers, or pharmaceutically acceptable salts, clathrates, or prodrugs thereof, which compounds are useful in treating respiratory diseases associated with influenza A viruses, such as for example H5N1 and its mutations. Pharmaceutical compositions comprising the compounds of the invention and methods of preparing the compounds of the invention are also disclosed.

  本发明涉及式(I)的化合物：其中A、B、D、E、m和R1-R5如本文所述，可以作为单一立体异构体或立体异构体混合物，或其药学上可接受的盐、包合物或前药，这些化合物在治疗与流感A病毒相关的呼吸系统疾病方面有用，例如H5N1及其突变体。本发明还公开了包含该化合物的制药组合物和制备该化合物的方法。
• Novel 5-cyano-prostacyclin derivatives and their use as agents for the treatment of autoimmune diseases
  申请人：Bayer Schering Pharma Aktiengesellschaft

  公开号：EP1988087A1

  公开（公告）日：2008-11-05

  This invention is directed to compounds of formula (I): where A, B, D, E, m, and R1 - R5 are as described herein, as single stereoisomers or as mixtures of stereoisomers, or pharmaceutically acceptable salts, clathrates, or prodrugs thereof, which compounds are useful in treating autoimmune diseases. Pharmaceutical compositions comprising the compounds of the invention and methods of preparing the compounds of the invention are also disclosed.

  本发明涉及式 (I) 化合物： 其中 A、B、D、E、m 和 R1 - R5 如本文所述，为单一立体异构体或立体异构体混合物，或其药学上可接受的盐、凝胶体或原药，这些化合物可用于治疗自身免疫性疾病。还公开了包含本发明化合物的药物组合物和制备本发明化合物的方法。