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A substituted pyrimidine as a prostaglandin d2 receptor antagonist

A technology of isomers and ester prodrugs, applied in metabolic diseases, medical preparations containing active ingredients, allergic diseases, etc., can solve problems such as the suspension of niacin treatment and the impact of patients' compliance with doctor's orders

Inactive Publication Date: 2013-04-03
AVENTIS PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These symptoms negatively impact patient compliance and, in severe cases, lead to discontinuation of niacin therapy

Method used

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  • A substituted pyrimidine as a prostaglandin d2 receptor antagonist
  • A substituted pyrimidine as a prostaglandin d2 receptor antagonist
  • A substituted pyrimidine as a prostaglandin d2 receptor antagonist

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0126] Reaction Scheme of Compound 1

[0127]

[0128] step 1

[0129] 2-(4-Trifluoromethoxy-phenyl)-ethylamine hydrochloride. (3)

[0130]

[0131] To a 500 mL hydrogenation reactor was added a solution of (4-trifluoromethoxy-phenyl)-acetonitrile (2) (25.0 g, 124.28 mmol), hydrochloric acid (12N, 25.89 mL, 310.70 mmol) in 200 mL of methanol and palladium / carbon (5wt%, 13.00g). The reactor was placed in a Parr-shaker and hydrogenated overnight (17 hours) at room temperature under 55 PSI hydrogen pressure. The catalyst was removed by filtration through a pad of celite, and the filtrate was concentrated under reduced pressure. The solid residue was dissolved in ethyl acetate / dichloromethane (300 mL, 1:1 v / v) and diluted slowly with 200 mL of heptane with vigorous stirring. The precipitated amine salt was collected by filtration to give the title compound (3) (25.50 g, 85%). LC / MS: Rt=1.96 min, MS m / z=206.

[0132] step 2

[0133] (6-Chloro-2-methoxy-pyrim...

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Abstract

The present invention is directed to a 2,6-substituted-4-monosubstitutedamino-pyrinudine compound of formula (I) as set forth herein, or an enantiomer thereof, or an ester prodrug or a pharmaceutically acceptable salt thereof, or a pharmaceutical composition comprising such a compound. The invention also includes a method of treatment of a patient by the administration of a pharmaceutically effective amount of such a compound.

Description

field of invention [0001] The present invention relates to a substituted pyrimidine compound, an enantiomer thereof, or an ester prodrug thereof, or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition comprising the compound, and its therapeutic effect by inhibiting prostaglandin D2 receptors. Pharmaceutical applications in body-regulated disease symptoms. Background of the invention [0002] The results of local allergen challenge in patients with allergic rhinitis, bronchial asthma, allergic conjunctivitis and atopic dermatitis showed that prostaglandin D2 "(PGD2)" levels rise rapidly. PGD2 has many inflammatory effects, such as increased vascular permeability of the conjunctiva and skin, increased nasal airway resistance, airway constriction, and eosinophil infiltration of the conjunctiva and trachea. [0003] PGD2, the major cyclooxygenase product of arachidonic acid, is produced from mast cells under immune-challenging conditions. [Lewis, RA,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D403/04A61K31/505A61P11/00
CPCC07D403/04A61P11/00A61P11/02A61P11/06A61P17/00A61P19/02A61P27/02A61P27/14A61P3/06A61P37/08A61P9/10A61P3/10C07D401/04A61K31/506
Inventor K.J.哈里斯J.C.阿奎亚沈伟国赵志城G.B.波利G.T.斯托克洛萨Y-M.乔伊-斯莱德斯基S.莱林
Owner AVENTIS PHARMA INC
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