4-(4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine | 90684-15-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-(4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine
• 英文别名: 4-(1,2,3,6-Tetrahydropyridin-4-yl)phenol
• CAS: 90684-15-4
• 化学式: C₁₁H₁₃NO
• mdl: MFCD08444193
• 分子量: 175.23
• InChiKey: KNEGDCIGZXOTBG-UHFFFAOYSA-N

物化性质

• 熔点：
  226-228 °C
• 沸点：
  330.3±42.0 °C(Predicted)
• 密度：
  1.120±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933399090

反应信息

• 作为反应物：
  描述：

  4-(4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 15.0h， 生成 2-{3-[4-(4-hydroxyphenyl)-3,6-dihydropyridin-1(2H)-yl]propyl}-4(3H)-quinazolinone
  参考文献：
  名称：

  合理的方法来发现聚（ADP-核糖）聚合酶的口服活性和脑可穿透的喹唑啉酮抑制剂。

  摘要：

  已发现一类新型的喹唑啉酮衍生物作为有效的聚（ADP-核糖）聚合酶-1（PARP-1）抑制剂。成功的关键是应用合理的发现策略，包括基于结构的设计，组合化学和经典SAR，以提高药效和生物利用度。新抑制剂被显示与NAD +的烟酰胺-核糖结合位点（NI位点）和腺苷-核糖结合位点（AD位点）结合。

  DOI：

  10.1021/jm0499256
• 作为产物：
  描述：

  1-benzyl-4-(4-benzyloxyphenyl)-4-hydroxypiperidine 在 10% palladium on activated carbon 氢气 、 盐酸 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 9.0h， 生成 4-(4'-hydroxyphenyl)-1,2,3,6-tetrahydropyridine
  参考文献：
  名称：

  [EN] 2-CYANOPYRROLOPYRIMIDINES AND PHARMACEUTICAL USES THEREOF
  [FR] 2-CYANOPYRROLOPYRIMIDINES ET UTILISATIONS PHARMACEUTIQUES DE CELLES-CI

  摘要：

  该发明涉及公式（I）中的吡咯嘧啶，其中Y代表-(CH2)t-O-或-(CH2)r-S-，p为1或2，r为1、2或3，t为1、2或3，或Y为-(CH2)j-或-CH=CH-，j为1或2；p为1或2，或Y为-(CH2)f-，f为1或2，p为1，以及进一步的基团和符号具有如本文所定义的含义；它们的制备，它们作为药物的用途，含有它们的药物组合物，利用这种化合物制备用于治疗神经病性疼痛的药物制剂的用途，以及用于治疗这种疾病的方法在动物中，尤其是在人类中。

  公开号：

  WO2004069256A1

文献信息

• NOVEL 3-(4(BENZYLOXY)PHENYL)HEX-4-INOIC ACID DERIVATIVE, METHOD OF PREPARING SAME AND PHARMACEUTICAL COMPOSITION FOR PREVENTING AND TREATING METABOLIC DISEASE INCLUDING SAME AS EFFECTIVE INGREDIENT
  申请人：HYUNDAI PHARM CO., LTD

  公开号：US20160024063A1

  公开（公告）日：2016-01-28

  The present invention relates to a novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative, a preparation method thereof, and a pharmaceutical composition comprising the same as an active ingredient for the prevention and treatment of metabolic disease. The novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of the present invention has excellent activities of activating GPR40 protein and promoting insulin secretion accordingly but has no toxicity when co-administered with other drugs. That is, the novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative, the optical isomer thereof, or the pharmaceutically acceptable salt thereof of the present invention can be co-administered with other drugs and can promote the activation of GPR40 protein significantly, so that the composition comprising the same as an active ingredient can be efficiently used as a pharmaceutical composition for the prevention and treatment of metabolic disease such as obesity, type I diabetes, type II diabetes, incompatible glucose tolerance, insulin resistance, hyperglycemia, hyperlipidemia, hypertriglyceridemia, hypercholesterolemia, dyslipidemia, and syndrome X, etc.

  本发明涉及一种新型的3-(4-(苄氧基)苯基)己-4-羧酸衍生物，其制备方法以及包含该衍生物作为活性成分的药物组合物，用于预防和治疗代谢性疾病。本发明的这种新型的3-(4-(苄氧基)苯基)己-4-羧酸衍生物、其光学异构体或其药用可接受盐，对于激活GPR40蛋白并相应地促进胰岛素分泌具有优良活性，且在与其他药物联合使用时没有毒性。也就是说，本发明的这种新型的3-(4-(苄氧基)苯基)己-4-羧酸衍生物、其光学异构体或其药用可接受盐，可以与其他药物联合使用，并且能显著促进GPR40蛋白的激活，使得包含其作为活性成分的组合物能有效地用作预防和治疗诸如肥胖、I型糖尿病、II型糖尿病、糖耐量异常、胰岛素抵抗、高血糖、高脂血症、高甘油三酯血症、高胆固醇血症、血脂异常和X综合症等代谢性疾病的药物组合物。
• [EN] COMPOUNDS AS INHIBITORS OF MACROPHAGE MIGRATION INHIBITORY FACTOR<br/>[FR] COMPOSÉS EN TANT QU'INHIBITEURS DU FACTEUR INHIBITEUR DE LA MIGRATION DES MACROPHAGES
  申请人：IMMUNOPHAGE BIOMEDICAL CO LTD

  公开号：WO2020186220A1

  公开（公告）日：2020-09-17

  The present invention provides compounds of Formula (I) shown above and their pharmaceutically acceptable salt, solvates, isomers, or prodrugs, as well as pharmaceutical compositions containing these compounds. Also provided by the invention is a method for treating a disorder mediated by macrophage migration inhibitory factor in a subject, comprising administering to the subject in need thereof a compound or a pharmaceutical composition of this invention.

  本发明提供了上述公式(I)所示的化合物及其药用可接受的盐、溶剂化物、异构体或前药，以及含有这些化合物的药物组合物。本发明还提供了一种用于治疗由巨噬细胞迁移抑制因子介导的疾病的方法，包括向需要治疗的对象施用本发明的化合物或药物组合物。
• Derivatives of (AZA)naphthalenesultam, their preparation and
  申请人：Rhone-Poulenc Sante

  公开号：US05021420A1

  公开（公告）日：1991-06-04

  This invention relates to a compound ##STR1## in which R.sub.1 represents a 1,2,3,6-tetrahydro-1-pyridyl radical substituted in the 4-position by (a) a phenyl radical, (b) a phenyl radical substituted by a halogen atom or an alkyl, hydroxy or alkoxy radical, (c) a 3-indolyl radical, (d) a 3-indolyl radical substituted on the nitrogen atom by an alkyl or alkylcarbonyl radical and/or in the 5-position by a halogen atom or (e) a 3-(5-hydroxyindolyl) radical. a 1-piperazinyl radical substituted in the 4-position by (a) a phenyl radical, (b) a phenyl radical substituted by an alkoxy, alkyl, hydroxy, nitro or amino radical or a halogen atom, (c) a 1,2-benzisothiazol-3-yl radical, (d) a 1,2-benzisoxazol-3-yl radical or (e) a 2-pyridyl radical. a piperidino radical substituted in the 4-position by (a) a phenyl radical, (b) a phenyl radical substituted by a halogen atom or a hydroxy, alkyl or alkoxy radical, (c) two phenyl radicals, (d) a bis(4-fluorophenyl)methylene radical, (e) a 4-fluorobenzoyl radical, (f) a 2-oxo-1-benzimidazolinyl radical, (g) a 2-oxo-1-benzimidazolinyl radical substituted in the 3-position by an alkylcarbonyl or benzoyl radical, (b) a hydroxy radical and a phenyl radical optionally substituted with an alkyl, alkoxy or hydroxy radical or a halogen atom, (i) a 3-indolyl radical, (j) a 3-indolyl radical substituted on the nitrogen atom by an alkyl or alkylcarbonyl radical and/or in the 5-position by a halogen atom or (k) a 3-(5-hydroxyindolyl) radical. either: R.sub.2 and R.sub.3, which are identical, represent a hydrogen or halogen atom and R.sub.4 represents a hydrogen atom or R.sub.2 and R.sub.4 represent a hydrogen atom and R.sub.3 represents a halogen atom or an acetylamino radical or R.sub.2 and R.sub.3 represent a hydrogen atom and R.sub.4 represents a halogen atom and R.sub.5 represents a --CH.dbd. group. or R.sub.2, R.sub.3 and R.sub.4 represent a hydrogen atom and R.sub.5 represents a nitrogen atom. R.sub.6 represents an alkylene chain containing 2 to 4 carbon atoms or a propylene chain substituted in the 1- or 3-position by an alkyl radical or in the 2-position by an alkyl, alkoxy, hydroxy, dialkylamino, piperidino, morpholino or thiomorpholino radical, with the reservation that when R.sub.6 represents a propylene radical substituted in the 2-position by a dialkylamino, piperidino, morpholino or thiomorpholino radical, R.sub.1 cannot be a radical containing a hydroxy radical, and their salts, are useful in therapy for their ability to block serotonin receptors.

  本发明涉及化合物##STR1## 其中R.sub.1代表1,2,3,6-四氢-1-吡啶基取代在4位上的基团，所述基团可以是(a)苯基基团，(b)被卤素原子或烷基、羟基或烷氧基取代的苯基基团，(c)3-吲哚基基团，(d)在氮原子上取代烷基或烷基羰基基团和/或在5位上取代卤素原子的3-吲哚基基团，或(e)3-(5-羟基吲哚基)基团；1-哌嗪基取代在4位上的基团，所述基团可以是(a)苯基基团，(b)被烷氧基、烷基、羟基、硝基或氨基基团或卤素原子取代的苯基基团，(c)1,2-苯并异噻唑-3-基基团，(d)1,2-苯并异恶唑-3-基基团或(e)2-吡啶基基团；取代在4位的哌啶基基团，所述基团可以是(a)苯基基团，(b)被卤素原子或羟基、烷基或烷氧基取代的苯基基团，(c)两个苯基基团，(d)双(4-氟苯基)亚甲基基团，(e)4-氟苯甲酰基基团，(f)2-氧代-1-苯并咪唑啉基团，(g)在3位上取代烷基羰基或苯甲酰基基团的2-氧代-1-苯并咪唑啉基团，(h)羟基基团和一个苯基基团，所述苯基基团可以选择取代烷基、烷氧基或羟基基团或卤素原子，(i)3-吲哚基基团，(j)在氮原子上取代烷基或烷基羰基基团和/或在5位上取代卤素原子的3-吲哚基基团，或(k)3-(5-羟基吲哚基)基团。R.sub.2和R.sub.3相同，分别代表氢原子或卤素原子，R.sub.4代表氢原子，或者R.sub.2和R.sub.4代表氢原子，R.sub.3代表卤素原子或乙酰氨基基团，或者R.sub.2和R.sub.3代表氢原子，R.sub.4代表卤素原子，R.sub.5代表--CH.dbd.基团，或者R.sub.2、R.sub.3和R.sub.4代表氢原子，R.sub.5代表氮原子。R.sub.6代表含有2到4个碳原子的烷基链或在1位或3位上取代烷基基团或在2位上取代烷基、烷氧基、羟基、二烷基氨基、哌啶基、吗啉基或硫代吗啉基的丙烯基链，但当R.sub.6代表在2位上取代二烷基氨基、哌啶基、吗啉基或硫代吗啉基的丙烯基链时，R.sub.1不能是含有羟基基团的基团。这些化合物及其盐在治疗中具有阻断血清素受体的能力。
• COMPOSITE PREPARATION, CONTAINING NOVEL 3-(4-(BENZYLOXY)PHENYL)HEX-4-INOIC ACID DERIVATIVE AND ANOTHER ACTIVE INGREDIENT, FOR PREVENTING OR TREATING METABOLIC DISEASES
  申请人：Hyundai Pharm Co., Ltd.

  公开号：EP3207928A2

  公开（公告）日：2017-08-23

  The present invention relates to a pharmaceutical composition for preventing or treating metabolic diseases, in which a novel 3-(4-(benzyloxy)phenyl)hex-4-inoic acid derivative and at least another active ingredient, which is selected from the group consisting of dipeptidyl peptidase-4 (DPPIV) inhibitor-based, sulfonylurea-based, thiazolidinedione (TZD)-based, biguanide-based, and sodium/glucose cotransporter 2 (SGLT2) inhibitor-based drugs, may be administered in combination or in the form of a composite preparation. The use of the composition of the present invention can provide a remarkably excellent blood sugar reducing effect in various animal diabetic disease models, and the composition of the present invention can be favorably used as a pharmaceutical composition for preventing or treating metabolic diseases, such as obesity, diabetes type I, diabetes type II, glucose intolerance symptoms, insulin resistance symptoms, hyperglycemia, hyperlipidemia, hypertriglyceridemia, hypercholesterolemia, dyslipidemia, and syndrome X.

  本发明涉及一种用于预防或治疗代谢性疾病的药物组合物，其中含有一种新型 3-(4-(苄氧基)苯基)己-4-氨基酸衍生物和至少另一种活性成分、其中，一种新型 3-(4-(苄氧基)苯基)己-4-嗪酸衍生物和至少另一种活性成分可以联合给药或以复合制剂的形式给药，这些活性成分选自由二肽基肽酶-4 (DPPIV) 抑制剂、磺酰脲类、噻唑烷二酮 (TZD)、双胍类和钠/葡萄糖共转运体 2 (SGLT2) 抑制剂组成的组。使用本发明的组合物可在各种动物糖尿病疾病模型中提供显著优异的降血糖效果，本发明的组合物可作为药物组合物用于预防或治疗代谢性疾病，如肥胖、I 型糖尿病、II 型糖尿病、葡萄糖不耐受症状、胰岛素抵抗症状、高血糖症、高脂血症、高甘油三酯血症、高胆固醇血症、血脂异常和 X 综合征。
• BROSSI, A.;GESSNER, W.;RONG-SEN, SHEN;ABELL, C. W., SYMP. CHEM. HETEROCYCL. COMPOUNDS (8TH) AND NUCL. ACID. COMPONENTS (6TH) +
  作者：BROSSI, A.、GESSNER, W.、RONG-SEN, SHEN、ABELL, C. W.

  DOI：——

  日期：——