(1S,3aS,3bS,9aR,9bS,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide

• 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: (1S,3aS,3bS,9aR,9bS,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
• 化学式: C₂₃H₃₆N₂O₂
• 分子量: 372.5
• InChiKey: DBEPLOCGEIEOCV-SKTQUGAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

文献信息

• Method for introducing a 1,2-double bond into 3-oxo-4-azasteroid compounds
  申请人：Scharer Norber

  公开号：US20060100434A1

  公开（公告）日：2006-05-11

  A process for preparing 17β-substituted 4-azaandrost-1-en-3-one compounds of the general formula (I): or a pharmaceutically approved salt thereof, where R is hydroxyl, optionally substituted, linear or branched (C 1 -C 2 )alkyl or (C 1 -C 12 )alkenyl; phenyl or benzyl; an —OR 1 radical, or an —NHR 1 radical, or an —NR 1 R 2 radical; R 1 is hydrogen, optionally substituted, linear or branched (C 1 -C 12 )alkyl or (C 1 -C 12 )alkenyl, or optionally substituted phenyl; R 2 is hydrogen, methyl, ethyl or propyl; or —NR 1 R 2 is a 5- or 6-membered heterocyclic ring, by (A) introducing protecting groups into the 3-keto-4-aza moiety of the corresponding 1,2-dihydro compound, so that a compound of the general formula (III) is formed: where R 3 is trialkylsilyl or, together with R 4 , the —C(O)—C(O)— or —C(O)—Y—C(O)— radical; R 4 is alkyloxycarbonyl or phenyloxycarbonyl, preferably Boc (=tert-butyloxycarbonyl); or trialkylsilyl, or, together with R 3 , the —C(O)—C(O)— or —C(O)—Y—C(O)— radical; Y is —[C(R 5 )(R 6 )] n — or —CH(R 5 )═CH(R 6 )—, or ortho-phenylene; R 5 and R 6 are each independently hydrogen, linear or branched (C 1-8 )alkyl or alkenyl, optionally substituted phenyl or benzyl; and n is an integer of 1 to 4; and where, in the case that R is hydroxyl, it has optionally reacted with a protecting group; (B) reacting the resulting compound in the presence (i) of a dehydrogenation catalyst, and in the presence of (ii) optionally substituted benzoquinone, allyl methyl carbonate, allyl ethyl carbonate and/or allyl propyl carbonate, and (C) removing the protecting groups R 3 and R 4 and optionally converting the resulting compound to a salt.

  一种制备一般式（I）的17β-取代4-氮杂睾酮-1-烯-3-酮化合物或其药学上批准的盐的方法，其中R为羟基，可选取代，线性或支链（C1-C2）烷基或（C1-C12）烯基；苯基或苄基；一个-OR1基团，或一个-NHR1基团，或一个-NR1R2基团；R1为氢，可选取代，线性或支链（C1-C12）烷基或（C1-C12）烯基，或可选取代的苯基；R2为氢，甲基，乙基或丙基；或-NR1R2为5-或6-成员杂环环；通过（A）将保护基引入相应的1,2-二氢化合物的3-酮-4-氮杂基中，从而形成一般式（III）的化合物：其中R3为三烷基硅基或与R4一起为-C（O）-C（O）-或-C（O）-Y-C（O）-基团；R4为烷氧羰基或苯氧羰基，优选为Boc（=叔丁氧羰基）；或三烷基硅基或与R3一起为-C（O）-C（O）-或-C（O）-Y-C（O）-基团；Y为-[C（R5）（R6）]n-或-CH（R5）═CH（R6）-，或邻苯二甲酰基；R5和R6独立地为氢，线性或支链（C1-8）烷基或烯基，可选取代的苯基或苄基；n为1至4的整数；在R为羟基的情况下，它可选择与保护基反应；（B）在（i）存在脱氢催化剂和（ii）可选取代苯醌，丙烯基甲基碳酸酯，丙烯基乙基碳酸酯和/或丙烯基丙基碳酸酯的情况下，反应所得化合物；（C）去除保护基R3和R4，并可选择将所得化合物转化为盐。
• Oxidized analogs of 17 beta-N-monosubstituted carbamoyl-4-aza 5 alpha-androst-1-en-3-ones
  申请人：Merck & Co., Inc.

  公开号：EP0271220A1

  公开（公告）日：1988-06-15

  The compounds of formula (I) wherein R is selected from hydrogen, methyl or ethyl, and R¹ is C1-12 straight or branched chain alkyl wherein one of the hydrogens is substituted by hydroxy, carboxylic acid or C1-4 alkyl ester, and A is -CH₂-CH₂ or -CH=CH-, and pharmaceutical formulations of the above compounds are active as testosterone 5α-reductase inhibitors and thus are useful for treatment of acne, seborrhea, female hirsutism or benign prostatic hypertrophy.

  式(I)化合物 其中 R 选自氢、甲基或乙基，R¹ 为 C1-12 直链或支链烷基，其中一个氢被羟基、羧酸或 C1-4 烷基酯取代，A 为 -CH₂-CH₂ 或 -CH=CH-，上述化合物的药物制剂作为睾酮 5α 还原酶抑制剂具有活性，因此可用于治疗痤疮、脂溢性皮炎、女性多毛症或良性前列腺肥大。
• FORMULATION AND METHOD FOR THE TREATMENT OF ANDROGENIC ALOPECIA
  申请人：Centro Internacional de Cosmiatría, S.A.P.I. de C.V.

  公开号：EP3750542A1

  公开（公告）日：2020-12-16

  The present invention relates to a topical formulation intended to be used for the treatment of androgenic or androgenetic baldness in men and women, with reduced side effects, especially with fewer collateral effects in the female population. The topical formulation comprises 0.01% to 10% by weight of Finasteride and a concentration of 1% to 5% by weight of Minoxidil in its free form or in an inert porous polymer. The combination of Finasteride and Minoxidil provides a synergistic effect against baldness. The formulation also comprises 0.15% by weight of retinol and is suitable for being applied to the scalp of the patient that requires it.

  本发明涉及一种外用制剂，旨在用于治疗男性和女性的雄激素性秃发或雄激素性秃发，可减少副作用，尤其是对女性群体的副作用较少。该外用制剂包括 0.01%至 10%（按重量计）的非那雄胺和浓度为 1%至 5%（按重量计）的米诺地尔（以其游离形式或在惰性多孔聚合物中）。非那雄胺和米诺地尔的组合具有防治秃发的协同作用。该制剂还含有 0.15%（按重量计）的视黄醇，适合涂抹在有需要的患者头皮上。
• Process for dehydrogenation of azaandros tane compounds
  申请人：Richter Gedeon Vegyeszeti Gyar Rt.

  公开号：US20030215902A1

  公开（公告）日：2003-11-20

  The invention relates to a process for the production of compounds of general formula (I), wherein R 1 is a —NH-tert-butyl group or a 4-methyl-piperidino group, by bioconversion of compounds of general formula (II), wherein R 1 is as described above, using a biocatalyst having steroid-&Dgr; 1 -dehydrogenase enzyme activity, wherein the activity of the enzyme needed for the bioconversion is produced by induction. 1

  本发明涉及通式(I)化合物的生产工艺，其中 R 1 是-NH-叔丁基或 4-甲基哌啶基，通过生物转化通式（II）化合物的工艺，其中 R 1 如上文所述，使用具有类固醇-Dgr； 1 -脱氢酶活性的生物催化剂，其中生物转化所需的酶活性是通过诱导产生的。 1
• 17 Beta-Substituted-4-aza-5-alpha-androstenones and their use as 5-alpha-reductase inhibitors
  申请人：Merck & Co., Inc.

  公开号：EP0155096B1

  公开（公告）日：1989-10-04