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Novel pyridine derivative and pyrimidine derivative (1)

A technology of compounds and hydrates, which is applied in the direction of drug combinations, active ingredients of heterocyclic compounds, cardiovascular system diseases, etc., and can solve problems such as unrecorded compounds and undisclosed HGFR inhibitory effects

Inactive Publication Date: 2007-01-31
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the compound of the present invention is not described in Patent Document 4, and the HGFR inhibitory effect of the compound disclosed in Patent Document 4 is not disclosed

Method used

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  • Novel pyridine derivative and pyrimidine derivative (1)
  • Novel pyridine derivative and pyrimidine derivative (1)
  • Novel pyridine derivative and pyrimidine derivative (1)

Examples

Experimental program
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Effect test

preparation example Construction

[0324] This step is a step of obtaining compound (1t) from compound (1ps) (compound (1ps) refers to compound (1p) and compound (1s) described in [Production method 1-B]). The same method as can be used.

[0325]

[0326] This step is a step of obtaining compound (1u) from compound (1t). The same method as can be used.

[0327]

[0328] This step is the protection group " R of compound (1u) 2 positions 102 The step of deprotecting -O-C(=O)-" and "P" to obtain compound (1n). Depending on the type of protecting group, deprotection using an acid such as hydrochloric acid or trifluoroacetic acid, using sodium hydroxide, Deprotection reaction of inorganic base such as potassium hydroxide, deprotection reaction using tetrabutylammonium fluoride, etc., deprotection reaction of catalytic hydrogenation reaction using palladium carbon, palladium hydroxide, etc. as catalyst, etc., to obtain compound (1n) .

[0329]

[0330] In this step, only the protecting groups "R" at the t...

Embodiment

[0586] The compounds of the present invention can be produced, for example, by the methods described in the following Preparations and Examples. However, the following examples are illustrative only, and the compounds of the present invention are not limited to the following specific examples in any way.

[0587] Unless otherwise specified in the preparation examples and examples, YMC SIL-60-400 / 230W is used to represent silica gel for purification.

[0588] In addition, as the LC-MS purification conditions, unless otherwise specified, the conditions described below were employed.

[0589] ODS column (WakopakR Combi ODS Column, or YMC Combi ODS-A)

[0590] Solvent A liquid 0.1% trifluoroacetic acid-water, B liquid 0.1% trifluoroacetic acid-acetonitrile

[0591] Flow rate 30mL / min

[0592] retention time 10min

[0593] gradient

[0594] 0.00min A: 99%, B: 1%

[0595] 8.00min A: 20%, B: 80%

[0596] 8.20min A: 0%, B: 100%

preparation example 1

[0597] (Preparation example 1) 0.5M hexane solution of phenylacetyl isooxyacid

[0598] In a nitrogen atmosphere, oxalyl chloride (3.51 mL, 40.2 mmol) was added to a suspension of phenylacetamide (1.81 g, 13.4 mmol) in 1,2-dichloroethane (150 mL) at room temperature, and stirred at 110° C. one night. After cooling the reaction solution to room temperature, it was concentrated under reduced pressure, n-hexane (26.8 mL) was added thereto, and ultrasonic treatment was performed. The supernatant (yellow solution fraction) was used as the title reagent for subsequent reactions.

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PUM

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Abstract

The compounds represented by the following general formula or their salts or their hydrates have excellent hepatocyte growth factor receptor (HGFR) inhibitory activity, and exhibit antitumor activity, angiogenesis inhibitory activity or cancer metastasis inhibitory activity. In the formula, R 1 means C 1－6 Alkyl etc. R 2 and R 3 represents a hydrogen atom. R 4 , R 5 , R 6 and R 7 Same or different, means hydrogen atom, halogen atom, C 1－6 Alkyl etc. R 8 represents a hydrogen atom, etc. R 9 means C 1－6 Alkyl etc. V 1 represents an oxygen atom, etc. V 2 Represents an oxygen atom or a sulfur atom. W represents a group represented by the formula -NH-, etc. X represents a group represented by the formula -CH=, a nitrogen atom, or the like. Y represents an oxygen atom or the like.

Description

technical field [0001] The present invention relates to novel pyridine derivatives and pyrimidine derivatives or their salts or hydrates having hepatocyte growth factor receptor antagonistic activity, antitumor activity, angiogenesis inhibitory activity, and cancer metastasis inhibitory activity. Background technique [0002] According to reports, various tumors such as pancreatic cancer, gastric cancer, colorectal cancer, breast cancer, prostate cancer, lung cancer, kidney cancer, brain tumor, and ovarian cancer all appear to have hepatocyte growth factor receptor (Hepatocyte growth factor receptor; hereinafter referred to as "HGFR"). ”) overexpression (Non-Patent Document 1). Since the HGFR expressed in the above tumor cells is fixed or stimulated by hepatocyte growth factor (Hepatocyte growth factor; hereinafter referred to as "HGF") to cause autophosphorylation of tyrosine kinase in the intracellular region, it is considered to be related to cancer Exacerbation (abnorma...

Claims

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Application Information

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IPC IPC(8): C07D213/75C07D413/12C07D407/12C07D487/08C07D239/47A61P43/00A61P35/00A61P9/00A61P35/04A61P1/18A61P11/00A61P13/08A61P13/12A61P15/00A61P25/00A61K31/4439A61K31/5377A61K31/4409A61K31/4545A61K31/496A61K31/4427A61K31/551A61K31/506A61K31/505A61K31/444A61K31/44C07D213/73C07D239/46C07D239/48C07D401/12C07D401/14C07D403/12C07D409/12
CPCC07D401/14C07D401/12C07D403/12C07D213/75C07D409/12C07D213/73C07D239/47C07D413/12A61P1/18A61P11/00A61P13/08A61P13/12A61P15/00A61P25/00A61P35/00A61P35/04A61P43/00A61P9/00
Inventor 松岛知广高桥惠子船坂势津雄尾叶石浩
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