| US 7,541,445 B2 | ||
| Synthetic heparin pentasaccharides | ||
| Joachim Seifert, Forest Lake (Australia); Latika Singh, Forest Lake (Australia); Tracie E. Ramsdale, Sunnybank (Australia); Michael L. West, Birkdale (Australia); and Nicholas B. Drinnan, Highgate Hill (Australia) | ||
| Assigned to Alchemia Limited, Eight Miles Plains (Australia) | ||
| Appl. No. 10/488,677 PCT Filed Sep. 06, 2002, PCT No. PCT/AU02/01228 § 371(c)(1), (2), (4) Date Sep. 30, 2004, PCT Pub. No. WO03/022860, PCT Pub. Date Mar. 20, 2003. |
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| Claims priority of application No. PR7587 (AU), filed on Sep. 07, 2001. | ||
| Prior Publication US 2005/0080042 A1, Apr. 14, 2005 | ||
| Int. Cl. A61K 31/702 (2006.01); A61K 31/727 (2006.01); C08B 37/10 (2006.01); C07H 1/00 (2006.01) | ||
| U.S. Cl. 536—21 [536/123; 514/54; 514/56] | 14 Claims |
1. A pentasaccharide building block for the preparation of synthetic heparinoids, said building block being of General Formula
I,
 In which the configuration of the monosaccharidic units and the stereochemistry of the internal linkages is defined as D-gluco-alpha-1,4-D-glucurono-beta-1,4-D-Gluco-alpha-1,4-L-idurono-alpha-1,4-D-gluco,
and the substituents are defined as;
X1 is selected from the group consisting of hydroxy, C2 to C10; alkoxy; aryloxy, thioalkyl, thioaryl, imidoyl, tbutyldiphenylsilyloxy; a lipoaminoacid or other such group suitable for conjugation to delivery systems or solid supports;
and the stereochemistry may be alpha or beta; or an alpha methoxy group;
RH,RH1 and RH2 are benzyl;
RA is selected from the group consisting of an azido function, an NH-Dde, and NH-DTPM;
RS1, RS2 and RS5 are independently selected from the group consisting of alkylacyl and arylacyl;
RS3 is selected from the group consisting of 4-methoxyphenyl and 4-methoxybenzyl;
RS4 is selected from the group consisting of 4-methoxyphenyl and 4-methoxybenzyl;
RE1 is methyl;
RE2 is methyl;
RB is selected from the group consisting of an azido function, an NH-Dde and an NH-DTPM group;
RB1 is selected from the group consisting of an azido function, an NH-Dde and an NH-DTPM group;
RP1 is benzyl; and
RP2 is benzyl.
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