1,2,4-Triazolone Derivative

A technology of triazolone and derivatives, applied in the field of 1,2,4-triazolone derivatives

Active Publication Date: 2013-05-22
TAISHO PHARMACEUTICAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there is no report on the compounds with 1,2,4-triazolone skeleton disclosed in the present invention

Method used

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  • 1,2,4-Triazolone Derivative
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  • 1,2,4-Triazolone Derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0285] Hereinafter, reference examples, examples, and test examples are given to further describe the present invention in detail, but these do not limit the present invention and can be changed without departing from the scope of the present invention.

[0286] In Reference Examples and Examples, the "phase separator (Phase Separator)" used in the post-treatment refers to Biotage's ISOLUTE (registered trademark) phase separator. For "SNAP Cartridge KP-NH" purified by column chromatography, Biotage SNAPCartridge KP-NH was used, "SNAP Cartridge KP-Sil" was Biotage SNAPCartridge KP-Sil, and "SNAP Cartridge HP-Sil" was Biotage The company's SNAPCartridge HP-Sil, "Chromatorex NH" uses Cromatrex (registered trademark) NH manufactured by Fuji Silysia Chemical Co., Ltd. For purification using preparative thin layer chromatography (PTLC), Mercury silica gel 60F was used 254 , 20cm×20cm. Waters Sunfire prep C18 OBD, 5.0 μm, φ30×50 mm was used for “reversed phase column chromatography...

reference example P-A1

[0317] ?Reference Example P-A1: Synthesis of (3-chlorophenyl)(oxo)acetic acid

[0318] [chemical 18]

[0319]

[0320] In (3-chlorophenyl)(oxo)ethyl acetate (2.00g) in THF / MeOH solution (1:1) (48ml), add 2mol / L NaOH aqueous solution (24ml) under ice-cooling, at room temperature Stir overnight. After the solvent was distilled off under reduced pressure, a 3 mol / L HCl aqueous solution was added under ice-cooling. The precipitated solid was collected by filtration to obtain the title compound (2.00 g, colorless solid).

[0321] MS (ESI neg.) m / z : 183([M-H] － ).

[0322] The following compounds were synthesized by the same method as in Reference Example P-A1.

[0323] ?Reference Example P-A2: (3-Chloro-4-fluorophenyl)(oxo)acetic acid

[0324] [Synthesis from ethyl (3-chloro-4-fluorophenyl)(oxo)acetate]

[0325] [chemical 19]

[0326] .

reference example P-A3

[0327] ?Reference Example P-A3: Synthesis of (3-methoxyphenyl)(oxo)acetic acid

[0328] [chemical 20]

[0329]

[0330] A pyridine solution (27 ml) of 1-(3-methoxyphenyl)ethanone (8.00 g) and selenium dioxide (8.87 g) was stirred at an external temperature of 100°C for 4 hours. After standing to cool, the reaction liquid was filtered through Celait (registered trademark), diluted with EtOAc, washed with 1mol / L HCl aqueous solution and brine, and washed with Na 2 SO 4 to dry. The solvent was distilled off under reduced pressure to obtain the title compound (10.6 g, gray solid).

[0331] MS (ESI neg.) m / z : 179([M-H] － ).

[0332] The following compounds were synthesized by the same method as in Reference Example P-A3.

[0333] ?Reference Example P-A4: (4-fluoro-3-methoxyphenyl)(oxo)acetic acid

[0334] [Synthesis from 1-(4-fluoro-3-methoxyphenyl)ethanone]

[0335] [chem 21]

[0336]

[0337] MS (ESI neg.) m / z : 197([M-H] － ).

[0338] ?Reference Example P-A5: (...

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Abstract

The present invention provides a 1,2,4-triazolone derivative represented by Formula (1A) having an antagonistic activity on the arginine-vasopressin 1b receptor or a pharmaceutically acceptable salt thereof and provides a pharmaceutical composition comprising the compound or the salt as an active ingredient, in particular, a therapeutic or preventive agent exhibiting favorable pharmacokinetics in a disease such as mood disorder, anxiety disorder, schizophrenia, Alzheimer's disease, Parkinson's disease, Huntington's chorea, eating disorder, hypertension, gastrointestinal disease, drug addiction, epilepsy, cerebral infarction, cerebral ischemia, cerebral edema, head injury, inflammation, immune-related disease, or alopecia.

Description

technical field [0001] The present invention relates to a compound of 1,2,4-triazolone skeleton having antagonistic effect on the V1b receptor of arginine vasopressin (AVP) and a pharmaceutical composition containing the compound as an active ingredient, in particular to affective disorders, Anxiety disorder, schizophrenia, Alzheimer's disease, Parkinson's disease, Huntington's disease, eating disorder, hypertension, digestive organ disease, drug dependence, epilepsy, cerebral infarction, cerebral ischemia, cerebral edema, head Therapeutic or preventive agents for diseases such as trauma, inflammation, immune-related diseases, and alopecia. Background technique [0002] Arginine vasopressin (AVP) is a peptide composed of 9 amino acids. It is mainly biosynthesized in the hypothalamus. As a pituitary hormone, it is highly involved in the regulation of plasma osmotic pressure, blood pressure and body fluid volume. [0003] As for the AVP receptor, three subtypes of V1a, V1b, a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D249/12A61K31/4196A61K31/454A61K31/4545A61K31/46A61K31/5377A61K31/5386A61K31/553A61P7/10A61P9/10A61P9/12A61P17/02A61P17/14A61P25/00A61P25/08A61P25/14A61P25/16A61P25/18A61P25/22A61P25/28A61P25/36A61P29/00A61P37/00C07D401/04C07D401/10C07D403/10C07D405/12C07D413/10C07D451/06C07D491/107C07D498/08
CPCC07D413/10C07D413/14C07D491/107C07D403/10C07D405/10C07D491/08C07D405/12C07D451/06C07D249/12C07D498/08C07D401/10C07D401/04A61P1/00A61P17/00A61P17/02A61P17/14A61P25/00A61P25/08A61P25/14A61P25/16A61P25/18A61P25/22A61P25/28A61P25/36A61P29/00A61P3/04A61P37/00A61P43/00A61P7/00A61P7/10A61P9/00A61P9/10A61P9/12A61K31/5377
Inventor 桒田刚志吉永光周石坂知子若杉大介城川伸一服部信隆岛崎洋一宫腰直树
Owner TAISHO PHARMACEUTICAL CO LTD
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