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Heterocyclyl-substituted-tetrahydro-naphthalen-amine derivatives, their preparation and use as medicaments

A technology of amine derivatives and heterocyclic groups, applied in the field of tetralin amine compounds, can solve problems such as low sequence homology

Inactive Publication Date: 2010-03-17
LAB DEL DR ESTEVE SA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 5-HT 7 The receptor has been cloned from rat, mouse, guinea pig, and human cDNA, exhibiting a high degree of interspecies homology (approximately 95%), but uniquely, it has low sequence identity to other 5-HT receptors Origin (less than 40%)

Method used

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  • Heterocyclyl-substituted-tetrahydro-naphthalen-amine derivatives, their preparation and use as medicaments
  • Heterocyclyl-substituted-tetrahydro-naphthalen-amine derivatives, their preparation and use as medicaments
  • Heterocyclyl-substituted-tetrahydro-naphthalen-amine derivatives, their preparation and use as medicaments

Examples

Experimental program
Comparison scheme
Effect test

Embodiment A

[0476] N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N,N-dimethylamine

[0477]

[0478] To dissolve in CH 2 Cl 2 To a solution of 5-methoxy-2-tetralone (10.33 g, 58.62 mmol) in (400 mL) was added dimethylamine (5.6 M in EtOH, 14 mL, 76.206 mmol) and AcOH (0.46 mL, 5.862 mmol) ), and the mixture was stirred at room temperature for 4 hours. It was then cooled to 0 °C and NaB(OAc) was added within 20 min 3 H (0.45eq (equiv), 5.59g, 26.379mmol). After stirring at 0°C for 1 hour, NaB(OAc) was added within 30 min 3 H (1.0 eq, 12.42 g, 58.62 mmol). The reaction mixture was warmed to room temperature and stirred for 16h. The mixture was cooled to 0 °C again, and H was added slowly 2 O (250 mL). By adding NaHCO 3 Saturated aqueous solution, adjust the pH of the solution to 8.0, and stir the mixture at 0 °C for 15 min. layered, with CH 2 Cl 2 (4 x 100 mL) to extract the aqueous phase. Combine all organic phases and wash with anhydrous Na 2 SO 4 Dry and concentrate i...

Embodiment B

[0481] 6-(Dimethylamino)-5,6,7,8-tetralin-1-ol

[0482]

[0483] N-(5-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-N,N-dimethylamine (8.86 g, 43.156 mmol) was dissolved in CH 2 Cl 2 (200mL), cooled to 0°C, and added BBr within 20 minutes 3 (CH 2 Cl2 1.0M, 51.8mL, 51.788mmol). The reaction mixture was allowed to reach room temperature by stirring overnight (ca. 14h). The mixture was cooled to 0 °C again and NH was added slowly 3 aqueous solution (25%, 50 mL), and the mixture was stirred at 0° C. for 15 minutes. The salt was filtered off, the layers were separated, and the 2 Cl 2 (4 x 40 mL) to extract the aqueous phase. Combine all organic phases, wash with anhydrous Na 2 SO 4 Dry and concentrate in vacuo. The residue (6.99g) was dissolved in silica gel (30:70:2-100:0:2AcOEt / hexane / Et 3 N and 30:70:2 AcOEt / Hexane / Et 3 N-90:10:2AcOEt / MeOH / Et 3 Purification by flash chromatography on N) afforded 2.80 g of the title compound (Rf=0.3 (AcOEt / hexane / Et 3 N 10:10:2), m...

Embodiment C

[0486] N-Benzyl-N-(5-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)amine

[0487]

[0488] To dissolve in CH 2 Cl 2 Benzylamine (23 mL, 212.80 mmol) and AcOH (0.97 mL, 17.02 mmol) were added to a solution of 5-methoxy-2-tetralone (30 g, 170.24 mmol) in (250 mL), and the mixture was stirred at room temperature for 4 h. Then cool to 0°C and add NaB(OAc) within 20min 3 H (0.38eq, 13.71g, 64.69mmol). After stirring at 0°C for 1 hour, NaB(OAc) was added within 30 min 3 H (1.07eq, 38.61g, 182.16mmol). Join CH 2 Cl 2 (100 mL), the reaction mixture was warmed to room temperature and stirred for 15 h. The mixture was cooled to 0 °C again, and H was added slowly 2 O (200 mL). By adding NaHCO 3 Saturated aqueous solution (300 mL), the pH of the solution was adjusted to 8.0, and the mixture was stirred at 0° C. for 15 min. layered, with CH 2 Cl 2 (2 x 150 mL) to extract the aqueous phase. Combine all organic phases, wash with anhydrous Na 2 SO 4 Dry and concentrate in vacuo...

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Abstract

The present invention relates to heterocyclyl-substituted-tetrahydro-naphtalen-amine compounds of general formula (I) methods for their preparation, medicaments comprising these compounds as well as their use for the preparation of a medicament for the treatment of humans or animals, mediated by the 5-HT7 receptor affinity.

Description

technical field [0001] The present invention relates to heterocyclyl-substituted tetrahydronaphthalene amino compounds of general formula (I), their preparation methods, medicaments comprising these compounds and their use in the preparation of medicaments for treating humans or animals. Background technique [0002] The search for new therapeutic agents has been greatly aided in recent years by a better understanding of the structure of proteins and other biomolecules associated with target diseases. One important class of proteins that has been the subject of extensive study is the serotonin (serotonin, 5-HT) receptor family. 5-HT discovered in 1993 7 Receptors belong to this family and have attracted great interest as valuable new drug targets (Terrón, J.A. Idrugs, 1998, vol.1, no.3, pages 302-310: "The 5HT 7 receptor: A target for novel therapeutic venues? "). [0003] 5-HT 7 The receptor has been cloned from rat, mouse, guinea pig, and human cDNA, exhibiting a hig...

Claims

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Application Information

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IPC IPC(8): C07D231/12A61K31/415A61P25/18C07D213/38C07D261/08C07D307/52C07D333/20A61K31/42A61K31/341A61K31/381A61K31/4418
CPCC07D231/12C07D333/20C07D213/38C07D261/08C07D307/52A61P1/04A61P1/06A61P13/10A61P25/04A61P25/06A61P25/18A61P25/20A61P25/22A61P25/24A61P25/28A61P9/12
Inventor 莫妮卡·加西亚-洛佩斯安东尼奥·托伦斯-霍韦尔赫尔穆特·H·布施曼
Owner LAB DEL DR ESTEVE SA
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