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Substd. pyridines and pyridazines with angiogenesis inhibiting activity

A representative, low-level technology, applied in the field of substituted pyridines and pyridazines, which can solve the problems of vascular proliferation, blindness, etc.

Inactive Publication Date: 2003-05-28
BAYER HEALTHCARE LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Overexpression of VEGF, such as under extremely low oxygen conditions, can lead to angiogenesis in the eye, leading to excessive proliferation of blood vessels and eventually blindness

Method used

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  • Substd. pyridines and pyridazines with angiogenesis inhibiting activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0173] experiment: Embodiment 1: Preparation of 1-(4-chlorophenylamino)-4-(4-pyridylthio)isoquinoline

[0174] Step 1: Preparation of intermediate A: 2.90 g, 19.07 mMol isoquinolone and 14.40 g, 33.68 mMol phosphorus pentabromide were melted together at 140°C. The melt turned into a red liquid and after about 10 minutes the reaction mixture solidified and was allowed to cool. The reaction mixture was crushed and poured into ice water. The resulting solid was filtered and air dried. wt. 5.50 g, yield 96%, mp. = 94-96°C. R f = 0.66 in a mixture of 40% ethyl acetate in hexane.

[0175] Step 2: A mixture of 1.00 g, 3.49 mMol of 1,4-dibromoisoquinoline (Intermediate A) and 4-chloroaniline from Step 1 was melted together at 140°C. The reaction mixture became a dark red liquid and solidified after about 10 minutes, which was allowed to cool. The reaction mixture was crushed and triturated with a 50 / 50 methanol / THF mixture, then filtered and air dried without further purif...

Embodiment 2

[0177] The title compound was prepared using the method used in Preparative Example 1, substituting 5-aminoindene for 4-chloroaniline in Step 2. Melting point 100-103C, TLC R f 0.40 (40% ethyl acetate in hexane). Example 3: Preparation of 1-(benzothiazol-6-ylamino)-4-(4-pyridylthio)isoquinoline

Embodiment 3

[0178] The title compound was prepared using the method used in Preparative Example 1, substituting 6-aminobenzothiazole for 4-chloroaniline in Step 2.

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Abstract

Substituted pyridines and pyridazines having angiogenesis inhibiting activity and generalized structural formula (I) wherein the ring containing A, B, D, E, and L is phenyl or a nitrogen-containing heterocycle; groups X and Y may be any of a variety of defined linking units; R<1> and R<2> may be defined independent substituents or together may be a ring-defining bridge; ring J may be an aryl, pyridyl, or cycloalkyl group; and G groups may be any of a variety of defined substituents. Pharmaceutical compositions containing these materials, and methods of treating a mammal having a condition characterized by abnormal angiogenesis or hyperpermeability processes using these materials are also disclosed.

Description

field of invention [0001] The present application relates to small molecule heterocyclic drugs, and more specifically, to substituted pyridines and pyridazines with angiogenesis inhibitory activity. Background of the invention [0002] Angiogenesis involves the de novo formation of blood vessels from endothelial cell precursors or hemangioblasts. The first vascular structures in the embryo are formed by angiogenesis. Angiogenesis involves the development of capillaries from existing blood vessels and is the primary mechanism by which organs such as the brain and kidney form blood vessels. Although restricted to embryonic development, angiogenesis can occur in adults, for example during pregnancy, the female cycle, or wound healing. [0003] The major regulator of angiogenesis and angiogenesis in embryonic development and in certain angiogenesis-dependent diseases is vascular endothelial growth factor (VEGF; also known as vascular permeability factor,...

Claims

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Application Information

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IPC IPC(8): A61K31/4725A61K31/50A61K31/5025A61P9/10A61P17/06A61P19/02A61P29/00A61P31/12A61P31/22A61P35/00C07D237/04C07D333/00C07D401/06C07D401/12C07D401/14C07D403/12C07D403/14C07D405/14C07D417/12C07D417/14C07D487/04C07D491/04C07D491/048C07D495/04C07D513/04
CPCC07D495/04C07D401/12C07D417/14C07D491/04C07D513/04C07D417/12C07D487/04A61P17/06A61P19/02A61P29/00A61P31/12A61P31/22A61P35/00A61P9/10
Inventor J·P·杜马斯T·K·乔H·C·E·克吕恩德W·李D·纳加拉斯纳姆R·N·西布利N·苏S·J·博尔J·A·迪克松
Owner BAYER HEALTHCARE LLC
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