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Biphenyl and biphenyl-analogous compounds as integrin antagonists

A technology of compounds and residues, applied in the direction of compounds containing elements of group 3/13 of the periodic table, preparation of organic compounds, active ingredients of heterocyclic compounds, etc., can solve problems such as poorly active compounds

Inactive Publication Date: 2002-02-06
BAYER AG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, many experiments aimed at establishing integrin antagonists with biphenyl cores have only resulted in compounds with poor activity

Method used

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  • Biphenyl and biphenyl-analogous compounds as integrin antagonists

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Experimental program
Comparison scheme
Effect test

Embodiment 12

[0144] Then with a solution of 564 μl diisopropylethylamine in 13 ml tetrahydrofuran (THF) / dichloromethane (1:1) and 3.13 g 4-nitrophenyl chloroformate in 13 ml tetrahydrofuran (THF) / dichloromethane The solution in (1:1) treated the resin. Shake it at room temperature for 45 minutes, wash with tetrahydrofuran (THF) and dimethylformamide (DMF), add 1.07g propylamine (amine reagent) and 3.16ml diisopropylethylamine in 23ml dimethylformamide solution in (DMF). After shaking for 2 hours, the resin was washed with dimethylformamide (DMF), methanol, tetrahydrofuran (THF) and dichloromethane. To remove the product, the resin was shaken with 10 ml of trifluoroacetic acid (TFA) / dichloromethane for 1 hour, filtered, the filtrate concentrated in vacuo and purified on silica gel to give 210 mg of the title compound. Mass spectrum (ESI): 524. Retention time (HPLC): R t = 10.4. 1 H-NMR (400MHz, methanol) δ=7.67(s, 1H), 7.32-7.22(m, 4H), 7.17(d, 1H), 7.04(d, 2H), 6.77(s, 2H), 3.93(dd ,...

Embodiment 13

[0145] Preparation of (2R, S)-3-[3'-(3-benzylureido)-biphenyl-4-yl]-2-[2,4,6-trimethylbenzenesulfonate according to the method of Example 1.1 Amino]-propionic acid, except that benzylamine was used instead of propylamine as the amine reagent. Mass spectrum (ESI): 572. Retention time (HPLC): R t = 11.0. Example 1.3: (2R,S)-3-[3'-(3-(2-pyrrolidin-1-ylethyl)-ureido)-biphenyl-4-yl]-2-[2,4 , 6-trimethylbenzenesulfonylamino]-propionic acid

Embodiment 14

[0146](2R, S)-3-[3'-(3-(2-pyrrolidin-1-ylethyl)-ureido)-biphenyl-4-yl]-2-[ 2,4,6-Trimethylbenzenesulfonylamino]-propionic acid, except that 2-pyrrolidin-1-ylethylamine was used instead of propylamine as the amine reagent. Mass spectrum (ESI): 579. Retention time (HPLC): R t = 8.3. Example 1.4: (2R,S)-3-[3'-(3-(pyridin-2-ylmethylureido)-biphenyl-4-yl]-2-[2,4,6-trimethyl phenylsulfonylamino]-propionic acid

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Abstract

The present invention relates to biphenyl and biphenyl-analogous compounds, their preparation and use as pharmaceutical compositions, as integrin antagonists and in particular for the production of pharmaceutical compositions for the treatment and prophylaxis of cancer, arteriosclerosis, restenosis, osteolytic disorders such as osteoporosis and ophthalmic diseases. The compounds according to the invention have formula (1) wherein R<1>, R<2>, U, V, A, B, W, R<3>, C and R<4> have the meaning as defined in the claims.

Description

field of invention [0001] The present invention relates to novel biphenyl and biphenyl-like compounds, their preparation and their use as pharmaceutical compositions, as integrin antagonists, in particular in the preparation of medicinal preparations for the treatment and prevention of the following diseases Use in the composition: cancer, arteriosclerosis, restenosis, osteolytic diseases such as osteoporosis, rheumatoid arthritis and eye diseases. Background of the invention [0002] Integrins are heterodimeric transmembrane proteins found on the surface of cells that play an important role in the attachment of cells to the extracellular matrix. They recognize extracellular glycoproteins such as fibronectin or vitronectin on the extracellular matrix through the RGD sequence (RGD is a single element of the amino acid sequence arginine-glycine-aspartic acid) present in these proteins. letter code) to achieve. [0003] In general, integrins, such as vitronectin receptors (al...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/12A61K31/192A61K31/27A61K31/277A61K31/341A61K31/381A61K31/40A61K31/415A61K31/417A61K31/4184A61K31/42A61K31/426A61K31/428A61K31/433A61K31/44A61K31/4402A61K31/4406A61K31/4409A61K31/5375A61P9/10A61P19/02A61P19/10A61P27/02A61P29/00A61P35/00C07C269/06C07C271/22C07C273/18C07C275/42C07C303/40C07C311/06C07C311/10C07C311/14C07C311/19C07C311/37C07C311/46C07C311/47C07C335/20C07D207/22C07D213/40C07D213/55C07D213/61C07D213/73C07D213/74C07D213/75C07D213/82C07D231/18C07D233/50C07D233/54C07D233/64C07D233/84C07D233/88C07D233/90C07D235/10C07D235/14C07D235/30C07D261/10C07D261/14C07D263/58C07D277/20C07D277/42C07D277/46C07D277/48C07D277/54C07D277/82C07D285/10C07D285/12C07D285/135C07D285/14C07D295/13C07D295/15C07D307/14C07D307/16C07D307/52C07D307/68C07D333/34C07D333/36C07D401/12C07D409/12C07D413/12C07D417/12C07D521/00C07F5/02
CPCC07D235/30C07D261/10C07D409/12C07D213/40C07D333/34C07D233/88C07C311/47C07D307/14C07D261/14C07D233/50C07D233/56C07C311/46C07D263/58C07D307/68C07D213/74C07C311/06C07D207/22C07C311/10C07D233/84C07C311/37C07D233/64C07D417/12C07D295/13C07D295/15C07D333/36C07D231/18C07D277/42C07D285/10C07C311/14C07C275/42C07D235/14C07D231/12C07D249/08C07D213/82C07C311/19C07D277/82C07D285/135C07D213/75C07C2101/02C07D413/12C07C335/20C07D307/52C07D285/14C07D401/12C07C271/22C07D277/54C07D277/48C07D213/55C07D233/90C07C2601/02A61P19/02A61P19/10A61P27/02A61P29/00A61P35/00A61P9/10
Inventor M·阿贝尔斯K·乌尔巴恩斯A·沃佩尔M·海特D·施米德特B·斯特尔特-卢德维格C·格尔德斯E·斯塔尔J·克尔德尼希U·布吕格梅尔K·卢斯蒂格
Owner BAYER AG
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