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Novel optically active aminopentane derivative

A technology of propylaminopentane and compounds, applied in the field of new optically active aminopentane derivatives, can solve the problem that the optical separation of racemic compounds is not so easy

Inactive Publication Date: 2001-03-14
THE FUJIMOTO CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, it turned out that the optical resolution of the racemic compounds in Japanese patent application JP 9-247445 is not so easy to implement due to their own flexible substitutes

Method used

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  • Novel optically active aminopentane derivative
  • Novel optically active aminopentane derivative
  • Novel optically active aminopentane derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Preparation of (-)-1-(benzofuran-2-yl)-2-propylaminopentane hydrochloride

[0019] Use the HPLC method to implement optical separation under the following conditions

[0020] 115 μl of 8 mg / ml (±)-1-(benzofuran-2-yl)-2-propylaminopentane hydrochloride (racemate) was injected directly into the HPLC.

[0021] HPLC: LC-6AD, Shimadzu, Kyoto, Japan.

[0022] Column: CHIRALPACK AD 20 mm φ x 250 mm (DAICEL)

[0023] Mobile phase: hexane: isopropanol: trifluoroacetic acid = 100: 2: 0.1

[0024] Flow rate: 120ml / min

[0025] Detector: SPD-10A UV / VIS detector (280 nm), Shimadzu, Kyoto, Japan

[0026] Humidity: room temperature

[0027] Melt oily (-)-1-(benzofuran-2-yl)-2-propylaminopentane in anhydrous ether, then add hydrogen chloride to the ether solution to make it saturated, thus forming hydrochloride .

[0028] Melting point: 165.0-166.0°C

[0029] lR: 3425, 2970, 2870, 2780, 2735, 2690, 2520, 2430, 1605,

[0030] 1590, 1472, 1455, 1255, 1167, 942, 805, 770, 760 cm ...

Embodiment 2

[0049] Determination of biogenic amines released from the brainstem of test rats by electrical stimulation

[0050] This method has been described in "Life Science" (Life Sci.) 58, 2101-2114 (1996), in which male test rats weighing 280-350 grams were slapped on the back of the head to stun them, and then removed Its brainstem (average weight about 800 mg) was immersed in oxygenated (95% O 2 with 5% CO 2 ) in Krebs' solution at 37°C for 30 minutes. Then, put 20 µl of 3 H-norepinephrine solution (1-[7,8- 3 H]-norepinephrine; specific activity: 30-50 Ci / mmol; Amersham) was added to the test preparation and absorbed for 45 minutes. The composition of Krebs solution is [mmol / L]: Na + 137.4;K + 5.9, Ca 2+ 2.5, Mg 2+ 1.2, Cl - 120.2,H 2 PO - 4 1.2, HCO 3 - 25.0, SO 1.2, glucose 11.5, ascorbic acid 0.3, EDTA-2Na 0.03. Bajiline (12 mmol) was added to Krebs' solution to inhibit MAO activity during the uptake of the labeled mediator.

[0051] absorbing 3 After H-norepi...

Embodiment 3

[0056] Conditional Avoidance Job Effects in Shuttle Boxes

[0057] This method is described in Life Sci. 58.817-827 (1996). Conditioned avoidance reflex effects (CARs) were analyzed in a shuttle box using male and female test rats (weight 200-220 g) whose learning ability was reduced by administration of tetrabenazine. The device described therein according to Psychopharmacologia Journal, 10, 1-5 (1996) constitutes the apparatus used in the experiments. Wherein the above-mentioned male and female test rats (200-220 gram weight / only) are trained to pass through obstacles under the conditions of conditioned stimulus [CS (control signal), light flash and buzzing sound]. If they refused to do so, they were punished by electrical stimulation of their paws (1 mA), here unconditioned (US). If the rat did not respond to the above US within 5 seconds, it was considered an escape failure (EF). In addition, behavior that is not related to this condition is considered an inter-signal r...

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Abstract

A novel optically pure (-)-1-(Benzofuran-2-yl)-2-propylaminopentane as represented by the following formula, which contains no (+)-isomer, and the pharmaceutically acceptable acid salt thereof. These compounds have excellent CAE effect (catecholaminergic activity enhancer effect) which is the enhancing action of neurotransmitter catecholamine release, and are useful as psychotropic composition, antidepressants, composition for treating Parkinson's disease and / or Alzheimer's disease.

Description

technical field [0001] The present invention relates to a novel optically active aminopentane derivative, (-)-1-(benzofuran-2-yl)-2-propylaminopentane, which is substantially free of (+)-isomeric body, but also certain pharmaceutically acceptable acid salts, which can be used as effective compounds in pharmaceutical compositions, especially compositions for the treatment of psychiatric disorders, antidepressants, for the treatment of Parkinson's syndrome and and / or compositions for Alzheimer's disease. Background of the invention [0002] It is well known that ethylamine derivatives have many biological effects. In particular aromatic ethylamine derivatives are regarded as promising compositions for the treatment of psychiatric diseases. Because they have a releasing effect by flushing out catecholamines stored in the central nervous system. However, it must be pointed out that the above-mentioned compositions have stimulant-like side effects, such as neurotoxic effects a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/00A61K31/34A61K31/343A61P25/00A61P25/16A61P25/18A61P25/24A61P25/28A61P43/00C07D307/81
CPCC07D307/81A61P25/00A61P25/16A61P25/18A61P25/24A61P25/28A61P43/00A61K31/343
Inventor 约瑟夫·克诺尔米田文郎大出博功荣雅敏本寿昭安藤敬岛津诚一郎高畑和惠
Owner THE FUJIMOTO CO LTD
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