17α-Hydroxy-21-methyl-11β-[4-(N,N-dimethylamino)phenyl]-19-norpregna-4,9-diene-3,20-dione | 198414-21-0

• 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: 17α-Hydroxy-21-methyl-11β-[4-(N,N-dimethylamino)phenyl]-19-norpregna-4,9-diene-3,20-dione
• 英文别名: (8S,11R,13S,14S,17R)-11-[4-(dimethylamino)phenyl]-17-hydroxy-13-methyl-17-propanoyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 198414-21-0
• 化学式: C₂₉H₃₇NO₃
• 分子量: 447.618
• InChiKey: LOTAUDRYNLHJQO-DQFOBABISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  33
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  17α-Hydroxy-21-methyl-11β-[4-(N,N-dimethylamino)phenyl]-19-norpregna-4,9-diene-3,20-dione 在 对甲苯磺酸一水合物 、 potassium carbonate 、 三氟乙酸酐 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 17α-acetoxy-21-methyl-11β-[4-(N,N-dimethylamino)phenyl]-19-norpregna-4,9-diene-3,20-dione
  参考文献：
  名称：

  Structural modification of 19-norprogesterone I: 17-α-substituted-11-β-substituted-4-aryl and 21-substituted 19-norpregnadienedione as new antiprogestational agents

  摘要：

  本发明涉及具有以下一般式的化合物： 其中：R 1 是从羟甲基、硫甲基、二甲胺基、甲胺基、N-丁基、N-戊基、N-丁氧基、甲醛基、羟基乙氧基、乙酰基、氧代乙基二甲胺基和氧代乙基N-戊基等组成的群体中选择的成员；R 2 是从氢、卤素、烷基、酰基、羟基、烷氧基（例如，甲氧基、乙氧基、乙烯氧基、乙炔氧基、环丙氧基等）、乙酰氧基（例如，乙酰氧基、甘氨酸酯等）、烷基碳酸酯、环戊酰氧基、S-烷基、硫氰基、硫酰基和羰基氧基，其中R 6 是包括但不限于烷基（例如，甲基、乙基等）、烷氧酯（例如，-CH 2 OCH 3 ）和烷氧基（-OCH 3 ）在内的官能团；R 3 是从烷基、羟基、烷氧基和乙酰氧基等组成的群体中选择的成员；R 4 是从氢和烷基等组成的群体中选择的成员；X是从═O和═N-OR 5 等组成的群体中选择的成员，其中R 5 是从氢和烷基等组成的群体中选择的成员。 除了提供式I的化合物外，本发明还提供了使用式I的化合物的方法，其中这些化合物有利地用于拮抗内源孕酮；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；治疗子宫平滑肌瘤；治疗子宫肌瘤；抑制子宫内膜增生；诱导宫颈成熟；诱导分娩；以及避孕。

  公开号：

  US06900193B1

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：EP2348031A2

  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。
• 21-SUBSTITUTED PROGESTERONE DERIVATIVES AS NEW ANTIPROGESTATIONAL AGENTS
  申请人：——

  公开号：US20020025951A1

  公开（公告）日：2002-02-28

  A compound having the general formula: 1 in which: R 1 is a member selected from the group consisting of —OCH 3 , —SCH 3 , —N(CH 3 ) 2 ,—NHCH 3 , —CHO, —COCH 3 and —CHOHCH 3 ; R 2 is a member selected from the group consisting of halogen, alkyl, acyl, hydroxy, alkoxy, acyloxy, alkyl carbonate, cypionyloxy, S-alkyl and S-acyl; 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 uterine fibroids; to inhibit uterine endometrial proliferation; to induce labor; and for contraception.

  通式如下的化合物 1 其中R 1 是选自 -OCH 3 、-SCH 3 、-N(CH 3 ) 2 或 -NHCH 3 , -CHO, -COCH 3 和-CHOHCH 3 ; R 2 是选自卤素、烷基、酰基、羟基、烷氧基、酰氧基、碳酸烷基酯、环酰氧基、S-烷基和 S-酰基所组成的组的成员； 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；以及 X 从以下组中选出的成员 &boxH；O 和 ═N-OR 5 ，其中 R 5 选自由氢和烷基组成的组。 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 的化合物主要用于拮抗内源性孕酮；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；治疗子宫肌瘤；抑制子宫内膜增生；诱导分娩；以及避孕。
• 21-substituted progesterone derivatives as new antiprogestational agents
  申请人：Kim K. Hyun

  公开号：US20060276443A1

  公开（公告）日：2006-12-07

  A compound 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 , —CHO, —COCH 3 and —CHOHCH 3 ; R 2 is a member selected from the group consisting of halogen, alkyl, acyl, hydroxy, alkoxy, acyloxy, alkyl carbonate, cypionyloxy, S-alkyl and S-acyl; R 3 is a member selected from the group consisting of alkyl, hydroxy, alkoxy and acyloxy; IV 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 uterine fibroids; to inhibit uterine endometrial proliferation; to induce labor; and for contraception.
• 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.