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Antiviral macrocyclic compounds

A technology of compounds and metal complexes, applied in the directions of antiviral agents, active ingredients of heterocyclic compounds, drug combinations, etc., can solve problems such as vascular development, hematopoiesis and heart defects

Inactive Publication Date: 2005-04-06
GENZYME CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Interference with any of these important functions by binding of pre-B cell growth stimulating factor / stromal-derived factor (PBSF / SDF-1) to the CXCR-4 chemokine receptor will lead to vascular development, hematopoiesis and cardiac dysfunction. fatal flaw

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0101] N-[1,4,8,11-tetraazacyclotetradecyl-1,4-phenylene bis(methylene)]-2-(amino-methyl)pyridine hexahydrobromide ( AMD 3465)

[0102] White solid: Mp 200-205°C (dec); 1 H NMR (D 2 O)d 2.04(m, 4H), 3.20-3.40(m, 8H), 3.40-3.60(m, 8H), 4.34(s, 2H), 4.38(s, 2H), 4.51(s, 2H), 7.50 (m, 4H), 7.75(t, 1H, J=6.6Hz), 7.82(d, 1H, J=7.9Hz), 8.26(t, 1H, J=7.9Hz), 8.63(d, 1H, J=7.9Hz), 8.63(d, 1H, J= 5.3Hz); 13 C NMR (D 2 O)d 18.30,18.96,37.04,37.28,37.40,40.92,41.13,41.49,44.26,47.61,48.01,51.29,58.88,127.46,127.75,130.40,131.05,131.23,131.47,132.10,132.44,144.95,145.81,146.01 ; FAB MS m / z 493 (M+H 81 Br, 7), 491 (M+H 79 Br, 7), 411 (M+H, 100).

[0103] Analysis (C 24 h 38 N 66HBr); Calculated C, 32.36; H, 4.98; N, 9.44; Br, 53.21. Found C, 32.20; H, 5.00; N, 9.30; Br, 53.10.

Embodiment 2

[0105] N-[1,4,8,11-tetraazacyclotetradecyl-1,4-phenylenebis(methylene)]-N-methyl-2-(aminomethyl)pyridine hexahydro Bromate Hydrate (AMD 3538)

[0106] White solid: Mp 220-225°C (dec); 1 H NMR (D 2 O)d 2.06(m, 4H), 2.76(s, 3H), 3.20-3.65(m, 16H), 4.47(bs, 4H), 4.65(s, 2H), 7.54(bs, 4H), 7.80(t , 1H), 7.87(d, 1H), 8.28(t, 1H), 8.68(d, 1H); 13C NMR (D 2 O)d 18.14,18.75,18.89,36.74,37.04,37.15,37.62,40.38,40.72,40.91,41.28,44.05,47.50,56.98,58.88,60.28,127.60,128.86,130.78,130.96,132.16,132.64,144.91,145.04 , 146.12; FAB MS m / z 507 (M+H 81 Br, 27), 507 (M+H 79 Br, 22), 425 (M+H, 100).

[0107] Analysis (C 25 h 40 N 6 6HBr 1.5H 2 O); Calculated C, 32.04; H, 5.27; N, 8.97; Br, 51.16. Found C, 31.88; H, 5.30; N, 8.93; Br, 51.00.

Embodiment 3

[0109] N-[1,4,8,11-tetraazacyclotetradecyl-1,4-phenylene bis(methylene)]-4-(amino-methyl)pyridine hexahydrobromide ( AMD 3500)

[0110] White solid: mp 201-204°C (dec); 1 H NMR (D 2 O)d 1.91-2.12(m, 4H), 3.00-3.49(m, 16H), 4.13(s, 2H), 4.34(s, 2H), 4.53(s, 2H), 7.39-7.57(m, 4H) , 8.02 (d, 2H, J=6.3Hz), 8.74 (d, 2H, J=6.3Hz); 13C NMR (D 2 O)d 18.26, 18.88, 36.94, 37.29, 37.36, 40.89, 41.06, 41.44, 44.21, 47.61, 49.17, 51.43, 59.02, 127.84, 130.21, 131.64, 132.15, 132.45, 142.167, 15 M+H 81 Br, 8), 491 (M+H 79 Br, 10), 411(M+H, 83), 320(37), 247(58), 201(100).

[0111] Analysis (C 24 h 38 N 6 6HBr); Calculated C, 32.17; H, 4.95; N, 9.34; Br, 53.50. Found C, 32.16; H, 5.03; N, 9.41; Br, 53.28.

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Abstract

The present invention is drawn to novel antiviral compounds, pharaceutical compositions and their use. More specifically this invention is drawn to derivatives of monocyclic polyamines which have activity in standard tests against HIV- or FIV-infected cells as well as other biological activity related to binding of ligands to chemokine receptors that mediate a number of mammalian embryonic developmental processes.

Description

[0001] The present invention relates to novel antiviral compounds, pharmaceutical compositions and uses thereof. In particular, the present invention relates to monocyclic polyamines which are active in standard cell assays against HIV infection, but also have other biological activities related to ligand binding to chemokine receptors which regulate a number of mammalian embryonic developmental processes. The present invention also relates to methods of treating various diseases modulated by chemokine-ligand binding. Background of the invention [0002] About 40 human chemokines have been described, whose function is (at least in part) important for the motility of lymphocytes and tissue infiltration and extravasation of leukocytes (in response to stimuli) through complex and interleaved biological activities (see, e.g., P .Ponath, Exp.Opin.Invest.Drugs, 7:1-18, 1998). These chemotactic cytokines or chemokines constitute a class of proteins, approximately 8-10 kDa in size. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/381A61K31/395A61K31/4178A61K31/4353A61K31/44A61K31/4427A61K31/4433A61K31/444A61K31/496A61K31/497A61K31/52A61K31/675A61P1/00A61P19/02A61P21/02A61P25/00A61P31/12A61P31/18A61P35/00C07D257/02C07D401/06C07D401/12C07D403/12C07D409/12C07D471/06C07D471/08C07D473/00C07D487/08
CPCC07D473/00C07D409/12C04B35/632C07D403/12C07D471/06C07D401/12C07D401/06C07D257/02A61P1/00A61P19/02A61P21/02A61P25/00A61P31/12A61P31/18A61P35/00A61P9/00
Inventor G·J·布里杰E·M·伯林格王忠仁D·肖尔斯R·T·斯基勒D·E·博古茨基
Owner GENZYME CORP
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