Vaccine immunogens comprising disulphide bridged cyclised...

C - Chemistry – Metallurgy – 07 – K

Patent

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C07K 7/08 (2006.01) A61K 39/00 (2006.01) A61K 39/385 (2006.01) A61K 47/48 (2006.01) A61P 37/08 (2006.01) C07K 1/107 (2006.01) C07K 14/705 (2006.01) C07K 16/00 (2006.01) A61K 38/00 (2006.01) A61K 38/11 (2006.01)

Patent

CA 2420086

The present invention relates to a novel chemical process for the covalent conjugation of disulphide bridge cyclised peptides to immunogenic carrier molecules by thio-ether linkages to form vaccine immunogens. In particular, the novel chemistry involves reacting a thiolated carrier with a cyclic peptide containing a disulphide bridge, which cyclic peptide (herein a disulphide bridge cyclised peptide) has attached to it, usually via a linker, a reactive group capable of forming thio-ether bonds with the carrier. The invention further relates to activated peptide intermediates of the process, medicaments produced by the process, pharmaceutical compositions containing the medicaments, and the use of the pharmaceutical compositions in medicine. The process of the present invention is particularly useful for the preparation of highly pure immunogens for vaccines, comprising disulphide bridge cyclised peptides. Also novel immunogens are provided, based on peptides derived from the sequence of human IgE, which are useful in the immunotherpay of allergy. Accordingly, the invention relates also to a process for conjugation of IgE disulphide bridge cyclised peptides to carries, immunogens produced by the process and vaccines and pharmaceutical compositions comprising them and their use in the treatment of allergy.

La présente invention concerne un nouveau procédé chimique permettant la conjugaison covalente de peptides cyclisés par ponts bisulfure à des molécules de support immunogène par des liaisons thio-éther pour former des vaccins immunogènes. En particulier, ce nouveau procédé chimique consiste à faire réagir un support thiolé avec un peptide cyclique contenant un pont bisulfure. Ledit peptide cyclique (dans le cas présent un peptide cyclisé par pont bisulfure) présente, relié à lui, habituellement par un lieur, un groupe réactif pouvant former des liaisons thio-éther avec le support. L'invention concerne également des produits intermédiaires de peptides activés, des médicaments obtenus selon le procédé, des compositions pharmaceutiques contenant ces médicaments, et l'utilisation de ces compositions pharmaceutiques en médecine. Le procédé de la présente invention est particulièrement utile pour la préparation d'immunogènes de grande pureté pour des vaccins, y compris de peptides cyclisés par ponts bisulfure. L'invention concerne également de nouveaux immunogènes, obtenus à partir de peptides dérivés de la séquence de l'immunoglobuline E humaine, utiles dans l'immunothérapie de l'allergie. En conséquence, l'invention concerne également un procédé permettant la conjugaison de peptides cyclisés par ponts bisulfures de l'immunoglobuline E à des supports, des immunogènes obtenus selon le procédé, des vaccins et des compositions pharmaceutiques qui les comprennent, ainsi que leur utilisation dans le traitement de l'allergie.

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