2,3-dihydro-1'-methylspiro | 180082-53-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 2,3-dihydro-1'-methylspiro
• 英文别名: 1'-Methyl-2H-spiro[benzofuran-3,4'-piperidine]；1'-methylspiro[2H-1-benzofuran-3,4'-piperidine]
• CAS: 180082-53-5
• 化学式: C₁₃H₁₇NO
• 分子量: 203.284
• InChiKey: LKMOKFJULSQBCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3-dihydro-1'-methylspiro 在 palladium on activated charcoal copper(II) nitrate 、 氢气 、 乙酸酐 作用下， 以 乙醇 为溶剂， 生成 5-amino-2,3-dihydro-1'-methylspiro
  参考文献：
  名称：

  The Selective 5-HT_1B Receptor Inverse Agonist 1‘-Methyl-5-[[2‘-methyl-4‘- (5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]carbonyl]-2,3,6,7-tetrahydro- spiro[furo[2,3-f]indole-3,4‘-piperidine] (SB-224289) Potently Blocks Terminal 5-HT Autoreceptor Function Both in Vitro and in Vivo

  摘要：

  5-HT1 receptors are members of the G-protein-coupled receptor superfamily and are negatively Linked to adenylyl cyclase activity. The human 5-HT1B and 5-HT1D receptors (previously known as 5-HT1D beta and 5-HT1D alpha, respectively), although encoded by two distinct genes, are structurally very similar. Pharmacologically, these two receptors have been differentiated using nonselective chemical tools such as ketanserin and ritanserin, but the absence of truly selective agents has meant that the precise function of the 5-HT1B and 5-HT1D receptors has not been defined. In this paper we describe how, using computational chemistry models as a guide, the nonselective 5-HT1B/5-HT1D receptor antagonist 4 was structurally modified to produce the selective 5-HT1B receptor inverse agonist 5, 1'-methyl-5-[[2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]carbonyl]-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (SB-224289). This compound is a potent antagonist of terminal 5-HT autoreceptor function both in vitro and in vivo.

  DOI：

  10.1021/jm970457s
• 作为产物：
  描述：

  1,2,3,6-四氢-1-甲基-4-吡啶甲醇 在 偶氮二异丁腈 、 三正丁基氢锡 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 11.0h， 生成 2,3-dihydro-1'-methylspiro
  参考文献：
  名称：

  The Selective 5-HT_1B Receptor Inverse Agonist 1‘-Methyl-5-[[2‘-methyl-4‘- (5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]carbonyl]-2,3,6,7-tetrahydro- spiro[furo[2,3-f]indole-3,4‘-piperidine] (SB-224289) Potently Blocks Terminal 5-HT Autoreceptor Function Both in Vitro and in Vivo

  摘要：

  5-HT1 receptors are members of the G-protein-coupled receptor superfamily and are negatively Linked to adenylyl cyclase activity. The human 5-HT1B and 5-HT1D receptors (previously known as 5-HT1D beta and 5-HT1D alpha, respectively), although encoded by two distinct genes, are structurally very similar. Pharmacologically, these two receptors have been differentiated using nonselective chemical tools such as ketanserin and ritanserin, but the absence of truly selective agents has meant that the precise function of the 5-HT1B and 5-HT1D receptors has not been defined. In this paper we describe how, using computational chemistry models as a guide, the nonselective 5-HT1B/5-HT1D receptor antagonist 4 was structurally modified to produce the selective 5-HT1B receptor inverse agonist 5, 1'-methyl-5-[[2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]carbonyl]-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (SB-224289). This compound is a potent antagonist of terminal 5-HT autoreceptor function both in vitro and in vivo.

  DOI：

  10.1021/jm970457s

文献信息

• [EN] 1',3'-DISUBSTITUTED-4-PHENYL-3,4,5,6-TETRAHYDRO-2H, 1'H-[1, 4'] BIPYRIDINYL-2'-ONES<br/>[FR] 4-PHÉNYL-3,4,5,6-TÉTRAHYDRO-2H,1'H-[1, 4'] BIPYRIDINYL-2'-ONES 1', 3'-DISUSBSTITUÉES
  申请人：ORTHO MCNEIL JANSSEN PHARM

  公开号：WO2009033704A1

  公开（公告）日：2009-03-19

  The present invention relates to novel compounds, in particular novel pyridinone derivatives according to Formula (I) wherein all radicals are as defined in the application and claims. The compounds according to the invention are positive allosteric modulators of metabotropic receptors - subtype 2 ('mGluR2') which are useful for the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction and diseases in which the mGluR2 subtype of metabotropic receptors is involved. In particular, such diseases are central nervous system disorders selected from the group of anxiety, schizophrenia, migraine, depression, and epilepsy. The invention is also directed to pharmaceutical compositions and processes to prepare such compounds and compositions, as well as to the use of such compounds for the prevention and treatment of such diseases in which mGluR2 is involved.

  本发明涉及新型化合物，特别是根据式（I）中定义的新型吡啶酮衍生物，其中所有基团均如申请和权利要求中所定义。根据本发明的化合物是代谢型受体亚型2（'mGluR2'）的阳性变构调节剂，用于治疗或预防与谷氨酸功能障碍相关的神经系统和精神疾病，以及mGluR2代谢型受体亚型涉及的疾病。具体来说，这些疾病是来自焦虑、精神分裂症、偏头痛、抑郁症和癫痫等中枢神经系统疾病的选择性疾病。本发明还涉及制备这种化合物和组合物的药物组合物和方法，以及利用这种化合物预防和治疗mGluR2涉及的疾病。
• Use of 5HT.sub.1B receptor antagonist for the treatment of vascular
  申请人：SmithKline Beecham p.l.c.

  公开号：US06107328A1

  公开（公告）日：2000-08-22

  The present application is directed to the use of 5HT.sub.1B or 5HT.sub.1D receptor antagonists in the treatment of vascular diseases, in particular angina, Raynaud's syndrome, peripheral vascular syndrome or portal hypertension.

  本申请涉及使用5HT.sub.1B或5HT.sub.1D受体拮抗剂治疗血管疾病，特别是心绞痛、雷诺综合征、外周血管症候群或门静脉高压症。
• Tetracyclic spiro compounds, process for their preparation and their use
  申请人：SmithKline Beecham plc

  公开号：US05972951A1

  公开（公告）日：1999-10-26

  Novel piperidine derivatives of formula (I), processes for their preparation, pharmaceutical compositions containing them and their use as medicaments for the treatment of CNS disorders are disclosed.

  本发明揭示了式(I)的新型哌啶衍生物，其制备过程，含有它们的制药组合物以及它们作为治疗中枢神经系统疾病的药物的用途。
• Aminopyrrolidines as chemokine receptor antagonists
  申请人：George Dawn M.

  公开号：US20080176883A1

  公开（公告）日：2008-07-24

  The present invention is directed to novel aminopyrrolidines of formula I pharmaceutically acceptable salts thereof, metabolites thereof, isomers thereof, stereoisomers thereof or pro-drugs thereof, wherein the variables are as defined herein. The compounds of formula (I) are useful as chemokine receptor antagonists and as such would be useful in treating certain conditions and diseases, especially inflammatory conditions and diseases and proliferative disorders and conditions, for example, cancers.

  本发明涉及公式I的新型氨基吡咯烷及其药学上可接受的盐、代谢物、异构体、立体异构体或前药。其中变量的定义如本文所述。公式（I）化合物可用作趋化因子受体拮抗剂，因此可用于治疗某些疾病和病症，特别是炎症性疾病和病症以及增生性疾病和病症，例如癌症。
• NOVEL FUSED PYROLE DERIVATIVE
  申请人：Sone Toshihiko

  公开号：US20100190768A1

  公开（公告）日：2010-07-29

  The present invention relates to a compound represented by the formula (1) which is useful as a glucocorticoid receptor function regulating agent, an anti-inflammatory agent or an antidiabetic agent, or a pharmaceutically acceptable salt thereof: wherein R 1 is aralkyl, etc.; R 2 is H, etc.; —W 4 ═W 5 —W 6 ═W 7 — is a group of the formula: —CR 4 ═CR 5 —CR 6 ═CR 7 — (in which R 4 , R 5 , R 6 and R 7 are independently a group of the formula: -E-A (E is a single bond, etc., A is H or nitro, etc.)), etc.; R 8 is a group of the formula: —OR 11 (R 11 is H, etc.), etc.; R 9 is trifluoromethyl, etc.; R 10 is a group of the formula: —[C(R 13 )(R 14 )] n —R 15 (R 13 and R 14 are independently H, etc., n is an integer of 0 to 10, R 15 is a group of the formula: N(R 18 )R 19 (R 18 and R 19 form a nitrogen-containing heteromonocycle together with a nitrogen atom to which they are bonded), etc.).

  本发明涉及一种化合物，其化学式为(1)，它可作为糖皮质激素受体功能调节剂、抗炎剂或抗糖尿病剂，或其药学上可接受的盐使用：其中R1为芳基烷基等；R2为H等；-W4═W5-W6═W7-为以下式的基团：-CR4═CR5-CR6═CR7-(其中R4、R5、R6和R7独立地为以下式的基团：-E-A(E为单键等，A为H或硝基等))等；R8为以下式的基团：-OR11(R11为H等)等；R9为三氟甲基等；R10为以下式的基团：-[C(R13)(R14)]n-R15(R13和R14独立地为H等，n为0到10的整数，R15为以下式的基团：N(R18)R19(R18和R19与它们连接的氮原子一起形成含氮杂单环)等。