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Sulfated oligosaccharide derivatives

A kind of derivative and compound technology, applied in the field of sulfated oligosaccharide derivatives

Inactive Publication Date: 2014-05-14
PROGEN PHARMA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, PI-88 does not interact with AT III and thus exhibits no anti-Xa or AT III-mediated anti-IIa activity [8,9]

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0085] Embodiment 1: from Pichia total synthesis neutral manna-oligosaccharide (8-11)

[0086]

[0087] Benzyl 2-O-(3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl)-3,4,6-tri-O- Benzyl-α-D-mannopyranoside (24)

[0088] 3-O-allyl-2,4,6-tri-O-benzoyl-α-D-mannopyranosyl trichloroimidate [26] (902mg, 1.21mmol) and benzyl A mixture of 3,4,6-tri-O-benzyl-α-D-mannopyranoside [27] (723mg, 1.34mmol) in 1,2-DCE (10mL) on molecular sieves (1.0g of powder) under argon atmosphere (30 min). The mixture was cooled (0° C.) with continued stirring (10 minutes) before adding TMSOTf (219 μL, 1.21 mmol). After a period of time (10 minutes), Et was introduced 3N (100 μL) and the mixture was filtered. The solvent was evaporated and the residue was subjected to FC (10-50% EtOAc / hexanes) to give the tribenzoate (24) (1.14 g, 84%) as a colorless oil. 1 H NMR (CDCl 3 )δ3.67-3.81,3.88-3.95,4.06-4.15,4.30-4.35(4m,12H;H-2 I ,-3 I ,-4 I ,-5 I ,-6a I ,-6b I ,-3 II ,-5 II ,-6a II ,-6b I...

Embodiment 2

[0110] Embodiment 2: benzyl glycoside polysulfate (PG 500)

[0111]

[0112] Peracetate 12

[0113] The pentasaccharide 11 (1.03 g, 95% M5), sodium acetate (1.2 g) and acetic anhydride (50 mL) were heated under a drying tube at 140 °C overnight with stirring. The mixture was cooled to room temperature, evaporated to dryness, taken up in EtOAc, washed with brine (x3) and flash chromatographed (40 g silica gel, 80:20 EtOAc:Hx) to give a glassy 810mg peracetate 12. 1 H NMR (400MHz, CDCl 3 )δ6.14(d,0.84H,J=2.0,αHl I ),5.71(d,0.16H,J=0.9,βHl I ), 5.30-5.10 (m, 8H), 5.00-4.85 (m, 7H), 4.25-3.70 (m, 19H), 2.20-1.90 (m, 51H). for C 64 h 87 o 43 Calculated value of HRMS [M+H] + 1543.4623, measured value 1543.4599.

[0114] General method for direct saccharification of peracetylated oligosaccharides:

[0115] The alcohol (6 equiv) was added to the peracetate (eg, 12) (1 equiv) in MS in dry DCM (0.03M). In some cases, adding a small amount MS powder. Boron trifluoride e...

Embodiment 3

[0122] Embodiment 3: Octyl glucoside polysulfate (PG 501)

[0123]

[0124] Octyl Glycoside 14

[0125] The saccharification using 12 and octanol afforded the product (14) as a colorless gum, 207 mg, 66% (Rf = 0.41, hexane-EtOAc = 1:3). 1 H NMR (CDC1 3 ,400MHz)δ5.23-5.09(m,8H),4.96-4.82(m,8H),4.23-3.71(m,19H),3.59(dt,1H,J=9.4,6.8,OCH 2 R),3.35(dt,1H,J=9.4,6.8,OCH 2 R), 2.11, 2.10(2), 2.09(8), 2.06, 2.05, 2.04(4), 2.04(1), 2.03(8), 2.03, 2.02, 2.01, 1.99(3), 1.98(8), 1.96, 1.94 and 1.90 (16s, 48H, 16×Ac), 1.52 (quintet, 2H, J=7.2, CH 2 ),1.27-1.18(m,10H,(CH 2 ) 5 ),0.80(t,3H,J=7.2,CH 3 ); 13 C NMR (CDCl 3 ,100MHz)δ170.4(0)(2C),170.3(8)(2C),170.3,170.2,170.1,169.9(2C),169.8(2),169.7(5),169.6,169.5,169.4(4) ,169.3(5),169.3(16×CO,3 overlapping),99.1(2C),98.8,98.7,98.0(5×sugar-Cl),77.0,75.0,74.8(3),74.7(5),71.0 ,70.8,70.7,70.1,69.4(9),69.4(7),69.3(0),69.2(7),69.2,68.3,68.2(0),68.1(6),67.2,66.6(4),66.6( 0), 66.1, 65.4, 62.4, 62.3, 61.8 and 61.5 (25C, the sugar carbon ...

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Abstract

The invention relates to compounds which are polysufated oligosaccharide derivatives having activity as inhibitors of heparan sulfate-binding proteins and inhibitors of the enzyme heparanase; methods for the preparation of the compounds; compositions comprising the compounds, and use of the compounds and compositions thereof for the antiangiogenic, antimetastatic, anti-inflammatory, antimicrobial, anticoagulant and / or antithrombotic treatment, lowering of blood triglyceride levels and inhibition of cardiovascular disease of a mammalian subject.

Description

[0001] This application is a divisional application of Chinese Patent Application No. 200580006833.8 (PCT / AU2005 / 000314) with the filing date of March 4, 2005, and the title of the invention is "Sulfated Oligosaccharide Derivatives". technical field [0002] The invention described herein relates to compounds having activity as inhibitors of heparan sulfate-binding proteins and heparanases. In particular, the invention relates to sulfated oligosaccharide derivatives, although the scope of the invention is not necessarily limited thereto. In particular, the present invention relates to polysulfated oligosaccharide derivatives, said derivatization being preferably at C-1 at the reducing end and / or at C-6 at the non-reducing end of the monosaccharide unit. The present invention also relates to a method for preparing the compound, a composition comprising the compound, and the compound and the composition thereof have anti-angiogenic, anti-metastasis, anti-inflammatory, anti-micro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H11/00C07H15/18C07H15/04C07H5/06C07H1/00C07H3/06C07H3/04C08G65/00C08B37/00A61K31/7028A61K31/7024A61K31/795A61K31/77A61K31/702A61K31/7056A61K31/715A61P29/00A61P31/00A61P7/02A61P3/06A61P9/00A61P35/00A61P35/04A61K31/7016C07H5/04
CPCC07H3/04C07H3/06C07H11/00C07H15/04A61P1/00A61P11/06A61P19/02A61P25/00A61P27/02A61P29/00A61P3/00A61P31/00A61P31/22A61P35/00A61P3/06A61P35/04A61P37/06A61P43/00A61P7/02A61P9/00A61P9/10C07H3/00C07H5/00
Inventor V·费尔罗J·K·法尔威瑟T·卡洛丽刘立功
Owner PROGEN PHARMA LTD
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