US 8,013,190 B2 · Chemical composition with borane clusters for use as an HIV protease inhibitor

Chemical composition with borane clusters for use as an HIV protease inhibitor

AssigneesVysoka Skola Chemicko-Technologicka V Praze, Ustav Organicke Chemie A Biochemie Av Cz, Ustav Anorganicke Chemie Av Cz, Department of Virology, University of Heidelberg

InventorsVladimír Král, Petr Cigler, Jan Konvalinka, Milan Kozísek, Jana Prejdová, Bohumír Grüner, Jaromír Plesek, Martin Lepsík, Jana Pokorná, Hans-Georg Kräusslich, Jochen Bodem

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Abstract

The present invention provides novel HIV protease inhibitors containing substituted borane, carborane or metallacarborane clusters with 6 to 12 boron atoms in each cluster. The charge of each borane, carborane or metallacarborane cluster is 0, −1 or −2. The number of borane, carborane or metallacarborane clusters in the inhibitor molecule is 1 to 9, and the carborane clusters in metallacarborane inhibitors are coordinated to transition metal atom, selected from the group containing cobalt, iron, nickel and ruthenium. In the cluster, heteroatoms can be present, such as nitrogen, phosphorus, silicon, germanium, tin and sulphur. The present invention covers pharmaceutical compositions containing these inhibitors and their use, both in vitro and in vivo. They are characterized by high effectiveness and stability.

Claims3

Dependent claims

A HIV protease inhibitor composition comprising a compound of formula:

A—Z—(CH2CH2O)2—A
wherein A is an anionic metallacarborane cluster;
[(C2B9H11)2-3-M(III)](−)
wherein M is Fe or Co;
wherein Z is —(OCH2CH2)2—N+H(R1)—, —(OCH2CH2)2—N+(CH2CH3)2—, —(OCH2CH2)2—N(p-toluenesulfonyl)—, —(OCH2CH2)2—X—, —N+H2— or —S—;
wherein R1 represents hydrogen, C4 alkyl, tert-butyl, 2-hydroxyethyl, benzyl, A, or —(CH2CH2O)2—A,
wherein X represents —O—, —CH(C6H5)—CH(C6H5)—, —OCH2C(CH2OCH2C6H5)2CH2O—,

4 more elements

Dependencies are inferred from the claim text.

Facts

Application

10/597,408Filed 27 Jan 2005

Priority

CZ 2004-16229 Jan 2004

Published

US 2009/0012044 A18 Jan 2009

Granted

6 Sep 2011

Term ends

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Classification6 codes

C07F 15/065
Cobalt compounds: without a metal-carbon linkage
A61K 31/69
Medicinal preparations containing organic active ingredients: boron compounds
A61P 31/18
For RNA viruses: for HIV
C07F
Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen