Transcell Technologies, Inc.

Incara Research Laboratories

Advanced Medicine, Inc.

Intercardia, Inc.

Dashan Liu

Michael J Sofia

Ramesh Kakarla

Tin Yau Chan

Rakesh K Jain

Nicole T Hatzenbuhler

Rui Liang

Anna K Chen

Nigel Mark Allanson

Thomas C Zebovitz

Domingos J Silva

A combinatorial chemical library of compounds structurally related to the moenomycin class of antibiotics has the formula

Combinatorial library of moenomycin analogs and methods of producing same

A combinatorial chemical library of compounds structurally related to the moenomycin class of antibiotics has the formula ##STR1## wherein D is a donor mono- or disaccharide, A is an acceptor monosaccharide, and P-R is a lipophosphoglycerate mimetic group. Members of the library have a glycosidic linkage between the anomeric carbon of D and the C2 carbon of A, and the D-A moiety is in turn covalently linked through the anomeric carbon of A to the P-R group. Members of the library exhibit their greatest structural diversity in terms of substitutions occurring at the C3 position of the A residue, substitutions at the C2 position of the D residue, and different P-R groups used in assembling the compounds. Members of the library are preferably synthesized by solid phase techniques involving stepwise coupling of the respective units to a support, functionalizing the A and/or D saccharides either before or after immobilizing them on the support, and cleaving the assembled compounds from the support. Preferred functionalities attached to the sugar residues are amides, carbamates, ureas, sulfonamides, substituted amines, esters, carbonates, and sulfates. Exemplary P-R groups are derivatives of homoserine, glyceric acid, salicylates and mandelic acid. Members of the library can be screened for anti-microbial activity by contacting them with a culture of microbes and monitoring the growth rate of the microbes.

The present invention relates to a process for the preparation and manufacture of 3-amino-substituted glycosylated bile acid derivatives. Intermediates and related compounds are also disclosed. In particular, the present invention permits the conversion of cholic acid esters to the 3-amino-7,12-bis(glucosyl)cholic acid esters via an azide intermediate. Conditions for the purification and isolation of the desired product is also disclosed to provide an overall manufacturing process suitable for large-scale production.

Process for the manufacture of 3-amino-substituted glycosylated bile

The present invention relates to a process for the preparation and manufacture of 3-amino-substituted glycosylated bile acid derivatives. Novel intermediates and related compounds are also disclosed. In particular, the present invention permits the conversion of cholic acid esters to the 3-amino-7,12-bis(glucosyl)cholic acid esters via an azide intermediate. Conditions for the purification and isolation of the desired product is also disclosed to provide an overall manufacturing process suitable for large-scale production.

The present invention relates to a process for the preparation and manufacture of 3-amino-substituted glycosylated bile acid derivatives. Novel intermediates and related compounds are also disclosed.

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East Brunswick, NJ, United States of America

Dashan Liu