1-acetyl-6-(tert-butoxycarbonyl)amino-1,2-dihydro-2,2,4-trimethylquinoline | 487065-02-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-acetyl-6-(tert-butoxycarbonyl)amino-1,2-dihydro-2,2,4-trimethylquinoline
• 英文别名: (1-acetyl-2,2,4-trimethyl-1,2-dihydroquinolin-6-yl)-carbamic acid tertbutyl ester；tert-butyl N-(1-acetyl-2,2,4-trimethylquinolin-6-yl)carbamate
• CAS: 487065-02-1
• 化学式: C₁₉H₂₆N₂O₃
• 分子量: 330.427
• InChiKey: IBZVSQSOMRCRCD-UHFFFAOYSA-N

物化性质

• 沸点：
  464.9±45.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-acetyl-6-(tert-butoxycarbonyl)amino-1,2-dihydro-2,2,4-trimethylquinoline 在 aluminum (III) chloride 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 17.5h， 生成 1-(6-amino-2,2,4-trimethyl-4-phenyl-3,4-dihydro-2H-quinolin-1-yl)-ethanone
  参考文献：
  名称：

  TSH receptor antagonizing tetrahydroquinoline compounds

  摘要：

  本发明涉及使用一种化合物、一种药物组合物、化合物和一种用于治疗或预防对TSH受体介导途径敏感的哺乳动物中的疾病的工具包，包括治疗甲状腺功能亢进、格雷夫斯病、格雷夫斯眼病、格雷夫斯相关的胫部皮肤病、结节性甲状腺肿和甲状腺癌等疾病，包括向该哺乳动物施用式(I)的四氢喹啉化合物或其药学上可接受的盐的有效量。

  公开号：

  US09174940B2
• 作为产物：
  描述：

  4-甲基-3戊烯-2-酮 在 吡啶 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 6.25h， 生成 1-acetyl-6-(tert-butoxycarbonyl)amino-1,2-dihydro-2,2,4-trimethylquinoline
  参考文献：
  名称：

  TSH receptor antagonizing tetrahydroquinoline compounds

  摘要：

  本发明涉及使用一种化合物、一种药物组合物、化合物和一种用于治疗或预防对TSH受体介导途径敏感的哺乳动物中的疾病的工具包，包括治疗甲状腺功能亢进、格雷夫斯病、格雷夫斯眼病、格雷夫斯相关的胫部皮肤病、结节性甲状腺肿和甲状腺癌等疾病，包括向该哺乳动物施用式(I)的四氢喹啉化合物或其药学上可接受的盐的有效量。

  公开号：

  US09174940B2

文献信息

• Tetrahydroquinoline derivatives
  申请人：——

  公开号：US20040236109A1

  公开（公告）日：2004-11-25

  The present invention relates to tetrahydroquinoline derivatives having general formula (I) or a pharmaceutically acceptable salt thereof, wherein R 1 is formyl, (1-6C)alkylcarbonyl or (1-6C)alkylsulfonyl; R 2 and R 3 are H or (1-4C)alkyl; R 4 is phenyl; R 5 is (1-4C)alkyl; Y—X is (CO)—O, (SO) 2 —O, NHC(O)—O, NHC(S)—O, OC(O)—O, bond-O, C(O)—NH, S(O) 2 —NH, NHC(O)—NH, NHC(S)—NH, OC(O)—NH, bond-NH, NH—C(O), O—C(O), NH—S(O) 2 , or O—S(O) 2 or Y—X is a bond; R 6 is H, trifluormethyl, (1-6C)alkyl, 1- or 2-adamantyl(1-4C)alkyl, (2-6C)alkenyl, (3-9C)heteroaryl, (3-6C)cycloalkyl, (2-6C)heterocycloalkyl, (1-4C)alkylthio(1-4C)alkyl, (6-10C)aryl(1-4C)alkyl, (3-9C)heteroaryl(1-4C)alkyl, (3-6C)cycloalkyl(1-4C)alkyl, (2-6C)heterocycloalkyl(1-4C)alkyl, R 8 , R 9 -aminocarbonyl(1-4C)alkyl, R 8 , R 9 -amino(1-4C)alkyl, R 8 -oxycarbonyl(1-4C)alkyl, R 8 -oxy(1-4C)alkyl, R 8 -carbonyl(1-4C)alkyl or (6-10C)aryl; R 7 is H, (1-4C)alkyl, (1-4C)alkoxy, halogen, trifluoromethyl, cyano, nitro hydroxyl; and R 8 and/or R 9 is H, (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, (6-10C)aryl, (3-9C)heteroaryl, (6-10C)aryl(1-4C)alkyl, (3-9C)heteroaryl(1-4C)alkyl, (3-6C)cycloalkyl(1-4C)alkyl, (2-6C)heterocycloalkyl(1-4C)alkyl, (1-4C)(di)alkylamino(1-4C)alkyl, (1-4C)alkoxy(1-4C)alkyl, (1-4C)alkylthio(1-4C)alkyl, (1-4C)alkylcarbonylamino(1-4C)alkyl, (1-4C)alkoxycarbonyl(1-4C)alkyl, (1-4C)alkoxycarbonylamino(1-4C)alkyl, (3-6C)cycloalkyl, (2-6C)heterocycloylkyl, or R 8 and R 9 may be joined in a (2-6C)heterocycloalkyl ring. The present invention also relates to pharmaceutical compositions comprising said derivatives and the use of these derivatives to control fertility. 1

  本发明涉及具有一般式（I）或其药学上可接受的盐的四氢喹啉衍生物，其中R1是甲酰基，（1-6C）烷基羰基或（1-6C）烷基磺酰基; R2和R3是H或（1-4C）烷基; R4是苯基; R5是（1-4C）烷基; Y-X是（CO）-O，（SO）2-O，NHC（O）-O，NHC（S）-O，OC（O）-O，键-O，C（O）-NH，S（O）2-NH，NHC（O）-NH，NHC（S）-NH，OC（O）-NH，键-NH，NH-C（O），O-C（O），NH-S（O）2或O-S（O）2，或Y-X是键; R6是H，三氟甲基，（1-6C）烷基，1-或2-金刚烷基（1-4C）烷基，（2-6C）烯基，（3-9C）杂环芳基，（3-6C）环烷基，（2-6C）杂环环烷基，（1-4C）烷基硫（1-4C）烷基，（6-10C）芳基（1-4C）烷基，（3-9C）杂环芳基（1-4C）烷基，（3-6C）环烷基（1-4C）烷基，（2-6C）杂环环烷基（1-4C）烷基，R8，R9-氨基羰基（1-4C）烷基，R8，R9-氨基（1-4C）烷基，R8-氧羰基（1-4C）烷基，R8-氧（1-4C）烷基，R8-羰基（1-4C）烷基或（6-10C）芳基; R7是H，（1-4C）烷基，（1-4C）烷氧基，卤素，三氟甲基，氰基，硝基羟基; R8和/或R9是H，（1-4C）烷基，（2-4C）烯基，（2-4C）炔基，（6-10C）芳基，（3-9C）杂环芳基，（6-10C）芳基（1-4C）烷基，（3-9C）杂环芳基（1-4C）烷基，（3-6C）环烷基（1-4C）烷基，（2-6C）杂环环烷基（1-4C）烷基，（1-4C）（二）烷基氨基（1-4C）烷基，（1-4C）烷氧基（1-4C）烷基，（1-4C）烷基硫（1-4C）烷基，（1-4C）烷基羰基氨基（1-4C）烷基，（1-4C）烷氧基羰基（1-4C）烷基，（1-4C）烷氧基羰基氨基（1-4C）烷基，（3-6C）环烷基，（2-6C）杂环环烷基，或R8和R9可以连接在（2-6C）杂环环烷基环中。本发明还涉及包含所述衍生物的制药组合物以及使用这些衍生物控制生育的方法。
• Tetrahydorquinoline derivatives and their use as fsh receptor modulators
  申请人：Timmers Marius Cornelis

  公开号：US20060167047A1

  公开（公告）日：2006-07-27

  The present invention relates to tetrahydroquinoline derivatives having general formula (I) or a pharmaceutically acceptable salt thereof, wherein R 1 and R 2 are H, Me; R 3 is (2-6C)heterocycloalkyl(1-4C)alkyl, (2-5C)heteroaryl(1-4C)alkyl, (6C)aryl (1-4C)alkyl, (1-4C)(di)alkylaminocarbonylamino(2-4C)alkyl, (2-6C) heterocycloalkylcarbonylamino(2-4C)alkyl, R 5 -(2-4C)alkyl or R 5 -carbonyl(1-4C)alkyl; R 4 is (2-5C)heteroaryl, (6C)aryl, (3-8C)cycloalkyl, (2-6C)heterocycloalkyl or (1-6C) alkyl and R 5 is (di)(1-4C)alkylamino, (1-4C)alkoxy, amino, hydroxy, (6C)arylamino, (di)(3-4C)alkenylamino, (2-5C)heteroaryl(1-4C)alkylamino, (6C)aryl(1-4C) alkylamino, (di)[(1-4C)alkoxy(2-4C)alkyl]amino, (di)[(1-4C)alkylamino(2-4C) alkyl]amino, (di)[amino(2-4C)alkyl]amino or (di)[hydroxy(2-4C)alkyl]amino. The present invention also relates to pharmaceutical compositions comprising said derivatives and the use of these derivatives to regulate fertility.

  本发明涉及具有一般式（I）或其药学上可接受的盐的四氢喹啉衍生物，其中R1和R2为H，Me；R3为（2-6C）杂环脂肪环（1-4C）烷基，（2-5C）杂环芳基（1-4C）烷基，（6C）芳基（1-4C）烷基，（1-4C）（二）烷基氨基甲酰氨基（2-4C）烷基，（2-6C）杂环脂肪环甲酰氨基（2-4C）烷基，R5-（2-4C）烷基或R5-羰基（1-4C）烷基；R4为（2-5C）杂环芳基，（6C）芳基，（3-8C）环烷基，（2-6C）杂环脂肪环或（1-6C）烷基，R5为（二）（1-4C）烷基氨基，（1-4C）烷氧基，氨基，羟基，（6C）芳基氨基，（二）（3-4C）烯基氨基，（2-5C）杂环芳基（1-4C）烷基氨基，（6C）芳基（1-4C）烷基氨基，（二）[(1-4C）烷氧基（2-4C）烷基]氨基，（二）[(1-4C）烷基氨基（2-4C）烷基]氨基，（二）[氨基（2-4C）烷基]氨基或（二）[羟基（2-4C）烷基]氨基。本发明还涉及包含所述衍生物的制药组合物，以及使用这些衍生物调节生育能力的用途。
• TETRAHYDROQUINOLINE DERIVATIVES
  申请人：Van Straten Nicole Corine Renée

  公开号：US20120202996A1

  公开（公告）日：2012-08-09

  The present invention relates to tetrahydroquinoline derivatives having general formula I: or a pharmaceutically acceptable salt thereof, wherein R1 is formyl, (1-6C)alkylcarbonyl or (1-6C)alkylsulfonyl; R2 and R3 are H or (1-4C)alkyl; R4 is phenyl; R5 is (1-4C)alkyl; Y—X is C(O)—O, S(O)2-O, NHC(O)—O, NHC(S)—O, OC(O)—O, bond-O, C(O)—NH, S(O)2-NH, NHC(O)—NH, NHC(S)—NH, OC(O)—NH, bond-NH, NH—C(O), O—C(O), NH—S(O)2, or O—S(O)2 or Y—X is a bond; R6 is H, trifluoromethyl, (1-6C)alkyl, 1- or 2-adamantyl(1-4C)alkyl, (2-6C)alkenyl, (2-6C)alkynyl, (3-9C)heteroaryl, (3-6C)cycloalkyl, (2-6C)heterocycloalkyl, (1-4C)alkylthio(1-4C)alkyl, (6-10C)aryl(1-4C)alkyl, (3-9C)heteroaryl(1-4C)alkyl, (3-6C)cycloalkyl(1-4C)alkyl, (2-6C)heterocycloalkyl(1-4C)alkyl, R8,R9-aminocarbonyl(1-4C)alkyl, R8,R9-amino(1-4C)alkyl, R8-oxycarbonyl(1-4C)alkyl, R8-oxy(1-4C)alkyl, R8-carbonyl(1-4C)alkyl or (6-10C)aryl; R7 is H, (1-4C)alkyl, (1-4C)alkoxy, halogen, trifluoromethyl, cyano, nitro, hydroxyl; and R8 and/or R9 is H, (1-4C)alkyl, (2-4C)alkenyl, (2-4C)alkynyl, (6-10C)aryl, (3-9C)heteroaryl, (6-10C)aryl(1-4C)alkyl, (3-9C)heteroaryl(1-4C)alkyl, (3-6C)cycloalkyl(1-4C)alkyl, (2-6C)heterocycloalkyl(1-4C)alkyl, (1-4C)(di)alkylamino(1-4C)alkyl, (1-4C)alkoxy(1-4C)alkyl, (1-4C)alkylthio(1-4C)alkyl, (1-4C)alkylcarbonylamino(1-4C)alkyl, (1-4C)alkoxycarbonyl(1-4C)alkyl, (1-4C)alkoxycarbonylamino(1-4C)alkyl, (3-6C)cycloalkyl, (2-6C)heterocycloalkyl, or R8 and R9 may be joined in a (2-6C)heterocycloalkyl ring. The present invention also relates to pharmaceutical compositions comprising said derivatives and the use of these derivatives to control fertility.

  本发明涉及通式I的四氢喹啉衍生物或其药学上可接受的盐，其中R1为甲酰基，(1-6C)烷基羰基或(1-6C)烷基磺酰基; R2和R3为H或(1-4C)烷基; R4为苯基; R5为(1-4C)烷基; Y-X为C(O)-O、S(O)2-O、NHC(O)-O、NHC(S)-O、OC(O)-O、键-O、C(O)-NH、S(O)2-NH、NHC(O)-NH、NHC(S)-NH、OC(O)-NH、键-NH、NH-C(O)、O-C(O)、NH-S(O)2或O-S(O)2，或Y-X为键; R6为H、三氟甲基、(1-6C)烷基、1-或2-金刚烷基(1-4C)烷基、(2-6C)烯基、(2-6C)炔基、(3-9C)杂环芳基、(3-6C)环烷基、(2-6C)杂环环烷基、(1-4C)烷基硫(1-4C)烷基、(6-10C)芳基(1-4C)烷基、(3-9C)杂环芳基(1-4C)烷基、(3-6C)环烷基(1-4C)烷基、(2-6C)杂环环烷基(1-4C)烷基、R8，R9-氨基羰基(1-4C)烷基、R8，R9-氨基(1-4C)烷基、R8-氧羰基(1-4C)烷基、R8-氧(1-4C)烷基、R8-羰基(1-4C)烷基或(6-10C)芳基; R7为H、(1-4C)烷基、(1-4C)烷氧基、卤素、三氟甲基、氰基、硝基、羟基; R8和/或R9为H、(1-4C)烷基、(2-4C)烯基、(2-4C)炔基、(6-10C)芳基、(3-9C)杂环芳基、(6-10C)芳基(1-4C)烷基、(3-9C)杂环芳基(1-4C)烷基、(3-6C)环烷基(1-4C)烷基、(2-6C)杂环环烷基(1-4C)烷基、(1-4C)(二)烷基氨基(1-4C)烷基、(1-4C)烷氧基(1-4C)烷基、(1-4C)硫基(1-4C)烷基、(1-4C)烷基羰基氨基(1-4C)烷基、(1-4C)烷氧羰基(1-4C)烷基、(1-4C)烷氧羰基氨基(1-4C)烷基、(3-6C)环烷基、(2-6C)杂环环烷基，或R8和R9可以在一个(2-6C)杂环环烷基环中连接。本发明还涉及包含所述衍生物的制药组合物以及使用这些衍生物控制生育的方法。
• [EN] TETRAHYDROQUINOLINE DERIVATIVES<br/>[FR] DERIVES DE TETRAHYDROQUINOLINE
  申请人：AKZO NOBEL NV

  公开号：WO2004056780A3

  公开（公告）日：2004-08-05
• Identification of Substituted 6-Amino-4-phenyltetrahydroquinoline Derivatives:  Potent Antagonists for the Follicle-Stimulating Hormone Receptor
  作者：Nicole C. R. van Straten、Twan H. J. van Berkel、Dennis R. Demont、Willem-Jan F. Karstens、Remco Merkx、Julia Oosterom、Jürgen Schulz、Richard G. van Someren、Cornelis M. Timmers、Peter M. van Zandvoort

  DOI：10.1021/jm049676l

  日期：2005.3.1

  Substituted 6-amino-4-phenyl-tetrahydroquinoline derivatives are described that are antagonists for the G(s)-protein-coupled human follicle-stimulating hormone (FSH) receptor. These compounds show high antagonistic efficacy in vitro using a CHO cell line expressing the human FSH receptor. Antagonist 10 also showed a submicromolar IC50 in a more physiologically relevant rat granulosa cell assay and was found to significantly inhibit follicle growth and ovulation in an ex vivo mouse model. This compound class may open the way toward a novel, nonsteroidal approach for contraception.