# US 11,014,952 B2 · Stable hydrolysis-resistant synthetic polyribosylribitolphosphate derivatives as vaccines against Haemophilus influenzae type b

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- Number: US 11,014,952 B2
- Document ID: US11014952B2
- Status: Granted
- Kind: B2
- Application number: 16/320,732
- Filed: 2017-07-28
- Published: 2019-05-23
- Granted: 2021-05-25
- Earliest claimed: 2016-07-28
- Assignees: Max-Planck-Gesellschaft zur Forderung der Wissenschaften e.V.; Vaxxilon AG
- Applicants: Max-Planck-Gesellschaft Zur FöRderung Der Wissenschaften E.V.
- Inventors: Peter H. Seeberger; Claney Lebev Pereira
- Web page: https://patentgrep.com/patent/US11014952B2

## CPC

- C07H 15/04: attached to an oxygen atom of the saccharide radical
- A61K 39/12: Viral antigens
- A61K 39/385: Haptens or antigens, bound to carriers
- A61P 1/02: Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 31/04: Antibacterial agents
- A61P 37/04: Immunostimulants
- A61P 39/00: General protective or antinoxious agents
- C07H 15/26: Acyclic or carbocyclic radicals, substituted by hetero rings
- G01N 33/56983: {Viruses}
- Y02A 50/30: Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)
- Y02A: TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE

## 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).

## Claims

### Claim 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(CH3)2, or —OCH3.

### Claim 2

A saccharide selected from the group consisting of:

### Claim 3 (depends on 1)

The saccharide according to claim 1, conjugated with an immunogenic carrier through the nitrogen atom of the —O—(CH2)5—NH2 group.

### Claim 4 (depends on 1)

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

### Claim 5 (depends on 1)

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.

### Claim 6 (depends on 5)

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.

### Claim 7 (depends on 2)

The saccharide according of claim 2, conjugated with an immunogenic carrier through the nitrogen atom of the —O—(CH2)5—NH2 group.

### Claim 8 (depends on 2)

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