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2-phenoxy-n-(1,3,4-thiadizol-2-yl)pyridin-3-amine derivatives and related compounds as p2y1 receptor inhibitors for the treatment of thromboembolic disorders

A compound, technology of NR12R13, applied to 2-phenoxy-N-(1,3,4-thiadiazol-2-yl)pyridine-3 as a P2Y1 receptor inhibitor for the treatment of thromboembolic disorders - The field of amine derivatives and related compounds, which can solve the problems of lack of pharmacological properties

Inactive Publication Date: 2008-03-12
BRISTOL MYERS SQUIBB CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although inhibition of platelet reactivity is often viewed as definitive evidence of antithrombotic activity, these antagonists lack the pharmacological properties required for in vivo studies

Method used

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  • 2-phenoxy-n-(1,3,4-thiadizol-2-yl)pyridin-3-amine derivatives and related compounds as p2y1 receptor inhibitors for the treatment of thromboembolic disorders
  • 2-phenoxy-n-(1,3,4-thiadizol-2-yl)pyridin-3-amine derivatives and related compounds as p2y1 receptor inhibitors for the treatment of thromboembolic disorders
  • 2-phenoxy-n-(1,3,4-thiadizol-2-yl)pyridin-3-amine derivatives and related compounds as p2y1 receptor inhibitors for the treatment of thromboembolic disorders

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0523] 2-(2-tert-butylphenoxy)-N-(5-phenyl-1,3,4-thiadiazol-2-yl)pyridin-3-amine

[0524]

Embodiment 1a

[0526] 2-(2-tert-butylphenoxy)-3-isothiocyanatopyridine

[0527]

[0528] 2-(2-tert-butylphenoxy)-3-aminopyridine (Example 203b) (5.21 g, 21.5 mmol) and 1,1'-thiocarbonyl bis-2(1H)-pyridone (5 g, 21.5 mmol) in DCM (100 mL) was stirred at room temperature for 18 h. The mixture was evaporated and the solid was dissolved in hexane / DCM (50 mL, 9 / 1). The residual solid was removed by filtration and the solution was evaporated to give the title compound as a brown solid. (M+H) + =285.

Embodiment 1b

[0530] 4-(2-(2-tert-butylphenoxy)pyridin-3-yl)thiosemicarbazide

[0531]

[0532] A mixture of Example 1a (1 g, 3.51 mmol) and tert-butyl carbazate (465 mg, 3.51 mmol) in DCM (10 mL) was stirred at room temperature for 2 h. Trifluoroacetic acid (2 mL) was added, and the mixture was stirred for 2 h. The solvent was removed and the residue was dissolved in EtOAc (15 mL), washed with saturated sodium bicarbonate solution, dried (anhydrous MgSO 4 ), filtered and evaporated to give the title compound as a brown solid (1.32 g). (M+H) + =317.

[0533] Example 1

[0534] A mixture of Example 1b (100 mg, 0.32 mmol), benzoyl chloride (45 mg, 0.32 mmol) in DCM (2 mL) was stirred at room temperature for 18 h. Then trifluoroacetic acid (2 mL) was added, and the mixture was stirred for 6 h. The solvent was removed and the residue was purified by preparative HPLC to afford the title compound (6 mg, TFA salt) as a white powder. (M+H) + = 403; 1 H NMR (400MHz, DMSO d 6 )δppm 1.30 ...

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Abstract

The present invention provides novel heteroaryl compounds of formula (Ia) which are selective inhibitors of the human P2Y1 receptor. The invention also provides for various pharmaceutical compositions of the same and methods for treating diseases responsive to modulation of P2Y1 receptor activity. (Ia) or a stereoisomer, tautomer, pharmaceutically acceptable salt, or solvate thereof, wherein: ring A is a 5- to 6-membered heteroaryl comprising: carbon atoms and 1-4 ringheteroatoms selected from N, NR11, S(O)p, and O, wherein said heteroaryl is substituted with 0-4 R1; ring B is phenyl substituted with 0-4 R7, pyridyl substituted with 0-3 R7, or thienyi substituted with 0-2 R7; X is NH or NMe; Y is O or S; R5 is a -(CRfRf)n-C3-10 carbocycle substituted with 1-4 R5a, or a -(CRfRf)n-5- to 10-membered heterocycle comprising: carbon atoms and 1-4 heteroatoms selected from N, NR11, O, and S(O)p, wherein said heterocycle is substituted with 0-4 R5a; the other substituents and variables are defined in the claims.

Description

[0001] 【Cross application of related application】 [0002] This application claims priority to U.S. Provisional Patent Application No. 60 / 645,285, filed January 19, 2005, and U.S. Provisional Patent Application No. 60 / 749,317, filed December 9, 2005, the entirety of which The contents are incorporated herein by reference. 【Technical field】 [0003] The present invention provides a human P2Y 1 Novel heteroaryl compounds and their analogs are selective inhibitors of receptors. The present invention also provides various pharmaceutical compositions thereof and treatments responsive to P2Y 1 A method for the modulation of receptor activity in diseases. 【Background technique】 [0004] Purinergic receptors bind and activate many ribosylated (nucleotide) and unribosylated (nucleotide) purines. This feature is used to divide these receptors into two broad classes: P1 receptors (A1, A2a, A2b, and A3), which bind to and are activated by the nucleotide adenosine; and P2 receptors, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/12C07D413/12C07D401/12C07D213/74C07D417/14C07D277/42C07D277/56C07D513/04A61P7/02
Inventor 詹姆斯·C·萨顿皮祖兰雷珍·鲁尔亚历山大·拉休鲁克斯卡尔·蒂博尔特帕特里克·Y·S·拉姆
Owner BRISTOL MYERS SQUIBB CO
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