Stable hydrolysis-resistant synthetic polyribosylribitolphosphate derivatives as vaccines against Haemophilus influenzae type b

Patent metadata

Field	Value
Publication number	US-11014952-B2
Application number	US-201716320732-A
Country	US
Kind code	B2
Filing date	Jul 28, 2017
Priority date	Jul 28, 2016
Publication date	May 25, 2021
Grant date	May 25, 2021

Abstract

The present invention provides a stable synthetic saccharide of Hib polyribosylribitol-phosphate (PRP) derivative and conjugate thereof. Said saccharide, said conjugate and pharmaceutical compositions thereof are hydrolysis-resistant, long-term stable and useful for the prevention and/or treatment of diseases associated with Haemophilus influenzae, and more specifically of diseases associated with Haemophilus influenzae type b, preferably diseases selected from meningitis, pneumonia, and epiglotitis. They have general formula (I): wherein A is formula (II) or formula (III); B is formula (IV); C is formula (V); D is formula (VI); E is formula (VII); F is formula (VIII) or formula (IX).

First claim

The invention claimed is:

1. A saccharide of the formula (IV-1)

wherein
m is an integer selected from 1 to 9; and
Xa is H, F, —OCO—N(CH 3 ) 2 , or —OCH 3 .

2. A saccharide selected from the group consisting of:

3. The saccharide according to claim 1 , conjugated with an immunogenic carrier through the nitrogen atom of the —O—(CH 2 ) 5 —NH 2 group.

4. A pharmaceutical composition comprising an effective amount of a saccharide of claim 1 .

5. A vaccine composition comprising a saccharide according to claim 1 together with at least one pharmaceutically acceptable adjuvant, carrier, cryoprotectant, lyoprotectant, excipient and/or diluent.

6. The vaccine composition according to claim 5 further comprising at least one of diphtheria antigen, tetanus antigen, pertussis antigen, hepatitis B antigen, inactivated polio vaccine and inactivated rotavirus vaccine.

7. The saccharide according of claim 2 , conjugated with an immunogenic carrier through the nitrogen atom of the —O—(CH 2 ) 5 —NH 2 group.

8. A pharmaceutical composition comprising an effective amount of a saccharide of claim 2 .

Assignees

• Max Planck Gesellschaft
• Vaxxilon Ag

Inventors

• Seeberger Peter H
• Pereira Claney Lebev

Classifications

• A61P1/02

  Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis · CPC title

• C07H15/26

  Acyclic or carbocyclic radicals, substituted by hetero rings · CPC title

• A61K39/12

  Viral antigens · CPC title

• A61P11/00

  Drugs for disorders of the respiratory system · CPC title

• G01N33/56983

  Viruses · CPC title