11β-[4-(N,N-dimethylamino)phenyl]-17α-propionyloxy-19-norpregna-4,9-diene-3,10-dione

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 11β-[4-(N,N-dimethylamino)phenyl]-17α-propionyloxy-19-norpregna-4,9-diene-3,10-dione
• 英文别名: [(8S,11R,13S,14S,17R)-17-acetyl-11-[4-(dimethylamino)phenyl]-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl] propanoate
• 化学式: C₃₁H₃₉NO₄
• 分子量: 489.655
• InChiKey: IZPYWWUMQSUNFA-MJBQOYBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  丙酸 、 3,3,20,20-bis(ethylene-dioxy)-5α-17α-dihydroxy-11β-[4-(N,N-dimethylamino)-phenyl-]-19-norpregna-9(11)-ene 在 对甲苯磺酸 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 1.0h， 以47%的产率得到11β-[4-(N,N-dimethylamino)phenyl]-17α-propionyloxy-19-norpregna-4,9-diene-3,10-dione
  参考文献：
  名称：

  JP5770235

  摘要：

  公开号：

文献信息

• 17-alpha-substituted-11-beta-substituted-4-aryl and 21-substituted 19-norpregnadienedione as antiprogestational agents
  申请人：The Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services

  公开号：EP2033965A2

  公开（公告）日：2009-03-11

  The invention provides 17-alpha-substituted-11-beta-substituted-4-aryl and 21-substituted 19-norpregnadienediones as antiprogestational agents.

  本发明提供了 17-α-取代-11-β-取代-4-芳基和 21-取代 19-前二烯酮作为抗孕激素制剂。
• 17-Alpha-substituted-11-beta-substituted-4-aryl and 21-substituted 19-norpregnadienedione as antiprogestational agents
  申请人：The Government of the United States of America as represented by the Secretary of the Department of Health and Human Services

  公开号：EP2348030A2

  公开（公告）日：2011-07-27

  The invention provides 17-alpha-substituted-11-beta-substituted-4-aryl and 21-substituted 19-norpregnadienediones as antiprogestational agents.

  本发明提供了 17-α-取代-11-β-取代-4-芳基和 21-取代 19-前二烯酮作为抗孕激素制剂。
• Structural modification of 19-norprogesterone I: 17-alpha-substituted-11-beta-substituted-4-aryl and 21-substituted 19-norpregnadienedione as new antiprogestational agents
  申请人：Kim K. Hyun

  公开号：US20050143365A1

  公开（公告）日：2005-06-30

  The present invention relates, inter alia, to compounds having the general formula: in which: R 1 is a member selected from the group consisting of —OCH 3 , —SCH 3 , —N(CH 3 ) 2 , —NHCH 3 , —NC 4 H 8 , —NC 5 H 10 , —NC 4 H 8 O, —CHO, —CH(OH)CH 3 , —C(O)CH 3 , —O(CH 2 ) 2 N(CH 3 ) 2 , and —O(CH 2 ) 2 NC 5 H 10 ; R 2 is a member selected from the group consisting of hydrogen, halogen, alkyl, acyl, hydroxy, alkoxy (e.g., methoxy, ethoxy, vinyloxy, ethynyloxy, cyclopropyloxy, etc.), acyloxy (e.g., acetoxy, glycinate, etc.), alkylcarbonate, cypionyloxy, S-alkyl, —SCN, S-acyl and —OC(O)R 6 , wherein R 6 is a functional group including, but not limited to, alkyl (e.g., methyl, ethyl, etc.), alkoxy ester (e.g., —CH 2 OCH 3 ) and alkoxy (—OCH 3 ); R 3 is a member selected from the group consisting of alkyl, hydroxy, alkoxy and acyloxy; R 4 is a member selected from the group consisting of hydrogen and alkyl; and X is a member selected from the group consisting of ═O and ═N—OR 5 , wherein R 5 is a member selected from the group consisting of hydrogen and alkyl. In addition to providing the compounds of Formula I, the present invention provides methods wherein the compounds of Formula I are advantageously used, inter alia, to antagonize endogenous progesterone; to induce menses; to treat endometriosis; to treat dysmenorrhea; to treat endocrine hormone-dependent tumors; to treat meningiomas; to treat uterine leiomyomas; to treat uterine fibroids; to inhibit uterine endometrial proliferation; to induce cervical ripening; to induce labor; and for contraception.

  本发明主要涉及具有通式的化合物： 其中R 1 是选自 -OCH 3 、-SCH 3 、-N(CH 3 ) 2 , -NHCH 3 , -NC 4 H 8 , -NC 5 H 10 , -NC 4 H 8 O，-CHO，-CH(OH)CH 3 、-C(O)CH 3 ，-O(CH 2 ) 2 N(CH 3 ) 2 和-O(CH 2 ) 2 NC 5 H 10 ; R 2 是选自氢、卤素、烷基、酰基、羟基、烷氧基（如甲氧基、乙氧基、乙烯氧基、乙炔氧基、环丙氧基等）、酰氧基（如乙酰氧基、甘氨酸等）、烷基碳酸酯、环丙氧基、S-烷基、-SCN、S-酰基和-OC(O)R 所组成的组中的成员 6 其中 R 6 是官能团，包括但不限于烷基（如甲基、乙基等）、烷氧基酯（如 -CH 2 OCH 3 ）和烷氧基（-OCH 3 ); R 3 是从烷基、羟基、烷氧基和酰氧基组成的组中选出的成员； R 4 是从氢和烷基组成的组中选出的成员；X是从═O 和═N-OR 组成的组中选出的成员。 5 其中 R 5 是从氢和烷基组成的组中选出的成员。 除了提供式 I 的化合物外，本发明还提供了一些方法，其中式 I 的化合物有利地用于，除其他外，拮抗内源性孕酮；诱导月经；治疗子宫内膜异位症；治疗痛经；治疗内分泌激素依赖性肿瘤；治疗脑膜瘤；治疗子宫纵隔肌瘤；治疗子宫肌瘤；抑制子宫内膜增生；诱导宫颈成熟；引产；以及避孕。
• FORMULATIONS WITH IMPROVED BIOAVAILABILITY, COMPRISING A STEROID DERIVATIVE AND A POLYGLYCOLYSED GLYCERIDE
  申请人：Repros Therapeutics Inc.

  公开号：EP1940413A1

  公开（公告）日：2008-07-09
• STRUCTURAL MODIFICATION OF 19-NORPROGESTERONE I: 17-ALPHA-SUBSTITUTED-11-BETA-SUBSTITUTED-4-ARYL AND 21-SUBSTITUTED 19-NORPREGNADIENEDIONE AS NEW ANTIPROGESTATIONAL AGENTS
  申请人：The United States of America, as represented by the Secretary, Department of Health and Human Serv

  公开号：US20140107089A1

  公开（公告）日：2014-04-17

  Disclosed are compounds having the general formula: wherein R 1 -R 4 and X are as defined herein, pharmaceutical compositions including such compounds, and a method of treating a patient involving antagonizing the endogenous progesterone, such as in inducing menses and treating endometriosis, dysmenorrhea, endocrine hormone-dependent tumors, meningiomas, uterine leiomyomas, or uterine fibroids, inhibiting uterine endometrial proliferation, inducing cervical ripening, inducing labor, and in contraception.