17α-hydroxy-21-acetoxy-19-norpregna-4,9-diene-3,20-dione | 80097-85-4

• 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-acetoxy-19-norpregna-4,9-diene-3,20-dione
• 英文别名: [2-[(8S,13S,14S,17R)-17-hydroxy-13-methyl-3-oxo-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate
• CAS: 80097-85-4
• 化学式: C₂₂H₂₈O₅
• 分子量: 372.461
• InChiKey: XPQOYLKIGZYALP-WAGURGNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  17α-hydroxy-21-acetoxy-19-norpregna-4,9-diene-3,20-dione 以57.6的产率得到17α-hydroxy-21-acetoxy-19-norpregna-4,9-diene-3,20-dione
  参考文献：
  名称：

  [EN] 21-SUBSTITUTED PROGESTERONE DERIVATIVES AS NEW ANTIPROGESTATIONAL AGENTS
  [FR] DERIVES DE PROGESTERONE SUBSTITUES 21 POUVANT ETRE UTILISES COMME NOUVEAUX AGENTS ANTIPROGESTATIFS

  摘要：

  一种具有通式（I）的化合物，其中R1是从-OCH3，-SCH3，-N（CH3）2，-NHCH3，-CHO，-COCH3和-CHOHCH3组成的群体中选择的成员；R2是从卤素，烷基，酰基，羟基，烷氧基，酰氧基，烷基碳酸酯，环戊烯酰氧基，S-烷基和S-酰基组成的群体中选择的成员；R3是从烷基，羟基，烷氧基和酰氧基组成的群体中选择的成员；R4是从氢和烷基组成的群体中选择的成员；X是从=O和=N-OR5组成的群体中选择的成员，其中R5是从氢和烷基组成的群体中选择的成员。除了提供通式（I）的化合物外，本发明还提供了使用通式（I）的化合物的优势方法，其中包括拮抗内源性孕酮，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。

  公开号：

  WO1997041145A1
• 作为产物：
  描述：

  3-ethylenedioxy-17β-cyano-17α-chloromethyl(dimethyl)silyloxyestra-5(10),9(11)-diene 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 4.0h， 生成 17α-hydroxy-21-acetoxy-19-norpregna-4,9-diene-3,20-dione
  参考文献：
  名称：

  17-Alpha-substituted-11-beta-substituted-4-aryl and 21-substituted 19-norpregnadienediones as antiprogestational agents

  摘要：

  公开号：

  EP2348031B9

文献信息

• Structural modification of 19-norprogesterone I: 17-α-substituted-11-β-substituted-4-aryl and 21-substituted 19-norpregnadienedione as new antiprogestational agents
  申请人：Kim Hyun K.

  公开号：US06900193B1

  公开（公告）日：2005-05-31

  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。
• Process for preparing17alpha-acetoxy-11beta-[4-n,n(dimethylamino)phenyl]-21-methoxy-19-norpregna-4,9-diene -3,20-dione, intermediates useful in the process , and processes for preparing such intermediates
  申请人：——

  公开号：US20030060646A1

  公开（公告）日：2003-03-27

  A compound having general formula (I) 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. 1

  通式（I）的化合物，其中R1是从以下组中选择的成员：—OCH3，—SCH3，—N（CH3）2，—NHCH3，—CHO，—COCH3和—CHOHCH3; R2是从以下组中选择的成员：卤素，烷基，酰基，羟基，烷氧基，酰氧基，烷基碳酸酯，环戊酰氧基，S-烷基和S-酰基; R3是从以下组中选择的成员：烷基，羟基，烷氧基和酰氧基; R4是从以下组中选择的成员：氢和烷基; X是从以下组中选择的成员：—O和—N—OR5，其中R5是从以下组中选择的成员：氢和烷基。除了提供通式（I）的化合物外，本发明还提供了使用通式（I）的化合物的优点方法，包括拮抗内源性孕激素；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；抑制子宫内膜增殖；诱导分娩；以及用于避孕。
• 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。