Sulfur-containing bicyclic compounds

A compound, the technology of dimethylcyclohexane, which is applied in the field of sulfur-containing bicyclic compounds, can solve the problems of narrowing of the therapeutic window and limitation of utilization

Active Publication Date: 2017-11-24
ASTELLAS PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] On the other hand, baclofen has a narrow therapeutic window due to harmful side effects such as sedation and muscle weakness, so its use is limited

Method used

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  • Sulfur-containing bicyclic compounds
  • Sulfur-containing bicyclic compounds
  • Sulfur-containing bicyclic compounds

Examples

Experimental program
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Effect test

Embodiment

[0325] Hereinafter, the production method of the compound of formula (I) is demonstrated in further detail based on an Example. It should be noted that the present invention is not limited to the compounds described in the following examples. In addition, the production method of the raw material compound is shown in the production example. In addition, the production method of the compound of formula (I) is not limited to the production method of the specific examples shown below, and the compound of formula (I) can also be obtained by a combination of these production methods, or those skilled in the art method manufacturing.

[0326] The compounds shown in the Tables described below were produced by the above-mentioned production methods and methods obvious to those skilled in the art, or modified methods of these methods. In the table, the structures and physicochemical data of these example compounds and their production methods are shown. It should be noted that the s...

manufacture example 3

[0333] 2M NaOH aqueous solution (200mL) was added to a mixture of 2-acetamido-5-(4,4-dimethylcyclohexyl)thiophene-3-carboxamide (37.3g) and EtOH (200mL), at 80°C Heat and stir for 2 hours. After allowing the reaction mixture to cool to room temperature, 1M hydrochloric acid (500 mL) was added, followed by stirring at room temperature. The precipitate was collected by filtration to obtain 6-(4,4-dimethylcyclohexyl)-2-methylthieno[2,3-d]pyrimidin-4(3H)-one (26.3 g).

manufacture example 4

[0335] Add phosphorus oxychloride (14mL) and DMF ( 200 μL), heated to reflux at 150°C for 14 hours. After cooling the reaction mixture to room temperature, it was concentrated under reduced pressure. Chloroform, water and saturated sodium bicarbonate water were added to the residue and stirred. The reaction mixture was extracted with chloroform. The organic layer was washed successively with water and brine. Add MgSO to the organic layer 4 , activated carbon (2g), silica gel (100mL) and stirring, Celite filtered, concentrated under reduced pressure to obtain 4-chloro-6-cyclohexyl-2-methylthieno[2,3-d]pyrimidine (27.4g) .

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Abstract

The present invention provides a compound useful as a pharmaceutical composition for the prevention and/or treatment of schizophrenia and the like. The inventors of the present invention have conducted studies on pharmaceutical compositions for the prevention and/or treatment of schizophrenia, etc., which have a positive allosteric modulation effect (PAM effect) of GABAB, and confirmed that the sulfur-containing bicyclic compound is a PAM of the GABAB receptor, The present invention has thus been accomplished. The sulfur-containing bicyclic compound of the present invention has the PAM action of GABAB, and can be used as a preventive and/or therapeutic agent for schizophrenia and the like. (In the formula, X is CH, R1 is a lower alkyl group, R2 is a lower alkyl group, R3 is -H, R4 is -H, the A ring is a cyclohexane ring, and RY is a group shown in formula (III), Y is NH etc., RL is lower alkyl.)

Description

technical field [0001] The present invention relates to a pharmaceutical composition particularly useful for schizophrenia, cognitive impairment associated with schizophrenia (CIAS), cognitive dysfunction, Fragile X syndrome, autism spectrum syndrome, spasticity, A sulfur-containing bicyclic compound as an active ingredient of a pharmaceutical composition for treating anxiety disorders, substance dependence, pain, fibromyalgia, or Charcot-Marie-Tooth disease. Background technique [0002] γ-aminobutyric acid (GABA) is an ion channel type GABA A and metabolically regulated GABA B Representative inhibitory neurotransmitter that activates both receptors. GABA B Receptors are expressed in both presynaptic terminals and postsynaptic portions of most mammalian brains, and play a wide range of roles in physiology and psychopathology by modulating inhibitory synaptic transmission. GABA B The receptor is a G protein-coupled receptor (GPCR), which has seven transmembrane domains ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D495/04A61K31/519A61K31/5377A61K31/541A61K31/554A61P25/00A61P25/18A61P25/22A61P43/00C07D519/00
CPCC07D519/00C07D495/04C07D513/04A61P25/00A61P25/04A61P25/08A61P25/18A61P25/22A61P25/24A61P25/28A61P25/30A61P25/32A61P29/00A61P43/00A61K31/519A61K31/5377A61K31/541A61K31/554C07D495/08C07D495/10A61K31/5355
Inventor 白石宜之星井博昭濵口涉本庄绘理子宅和知文近藤雄二后藤贵行
Owner ASTELLAS PHARMA INC
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