# US 11,110,160 B2 · Glycoconjugation processes and compositions > Agents: this data is available as JSON from the patentgrep API and MCP server — see https://patentgrep.com/llms.txt - Number: US 11,110,160 B2 - Document ID: US11110160B2 - Status: Granted - Kind: B2 - Application number: 16/774,309 - Filed: 2020-01-28 - Published: 2020-08-06 - Granted: 2021-09-07 - Earliest claimed: 2012-08-16 - Assignees: Pfizer Inc. - Applicants: Pfizer Inc. - Inventors: Jianxin Gu; Jin-hwan Kim; Avvari Krishna Prasad; Yu-ying Yang - Web page: https://patentgrep.com/patent/US11110160B2 ## CPC - A61K 39/095: Neisseria - A61K 39/092: {Streptococcus} - A61K 45/06: Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca - A61K 47/64: Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent (peptidic linkers A61K47/65) - A61K 47/6415: {Toxins or lectins, e.g. clostridial toxins or Pseudomonas exotoxins} - A61K 47/646: {the entire peptide or protein drug conjugate elicits an immune response, e.g. conjugate vaccines} - A61P 31/00: Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics - A61P 31/04: Antibacterial agents - A61P 37/04: Immunostimulants - A61K 2039/6037: {Bacterial toxins, e.g. diphteria toxoid [DT], tetanus toxoid [TT]} - A61K 2039/6068: {Other bacterial proteins, e.g. OMP} - A61K 2039/627: {characterised by the linker} - 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 ## Abstract The invention provides eTEC linked glycoconjugates comprising a saccharide covalently conjugated to a carrier protein through a (2-((2-oxoethyl)thio)ethyl)carbamate (eTEC) spacer, immunogenic compositions comprising such glycoconjugates, and methods for the preparation and use of such glycoconjugates and immunogenic compositions. ## Claims ### Claim 1 A glycoconjugate comprising a Streptococcus pneumoniae-derived capsular polysaccharide conjugated to a carrier protein through a (2-((2-oxoethyl)thio)ethyl)carbamate (eTEC) spacer, wherein the polysaccharide is covalently linked to the eTEC spacer through a carbamate linkage, and wherein the carrier protein is covalently linked to the eTEC spacer through an amide linkage, as shown by formula (I): wherein the glycoconjugate comprises at least one covalent linkage between the carrier protein and the polysaccharide for every 4, 10, 15 or 25 saccharide repeat units of the polysaccharide. ### Claim 2 (depends on 1) The glycoconjugate of claim 1, wherein said glycoconjugate comprises at least one covalent linkage between the carrier protein and the polysaccharide for every 4 saccharide repeat units of the polysaccharide. ### Claim 3 (depends on 1) The glycoconjugate of claim 1, wherein said glycoconjugate comprises at least one covalent linkage between the carrier protein and the polysaccharide for every 10 saccharide repeat units of the polysaccharide. ### Claim 4 (depends on 1) The glycoconjugate of claim 1, wherein said glycoconjugate comprises at least one covalent linkage between the carrier protein and the polysaccharide for every 15 saccharide repeat units of the polysaccharide. ### Claim 5 (depends on 1) The glycoconjugate of claim 1, wherein said glycoconjugate comprises at least one covalent linkage between the carrier protein and the polysaccharide for every 25 saccharide repeat units of the polysaccharide. ### Claim 6 (depends on 1) The glycoconjugate of claim 1, wherein said Streptococcus pneumoniae-derived capsular polysaccharide is selected from the group consisting of Pn-serotype 10A, 11A, 22F, and 33F capsular polysaccharide. ### Claim 7 (depends on 1) The glycoconjugate of claim 1, wherein said Streptococcus pneumoniae-derived capsular polysaccharide is a Pn-serotype 10A capsular polysaccharide. ### Claim 8 (depends on 1) The glycoconjugate of claim 1, wherein said Streptococcus pneumoniae-derived capsular polysaccharide is a Pn-serotype 11A capsular polysaccharide. ### Claim 9 (depends on 1) The glycoconjugate of claim 1, wherein said Streptococcus pneumoniae-derived capsular polysaccharide is a Pn-serotype 22F capsular polysaccharide. ### Claim 10 (depends on 1) The glycoconjugate of claim 1, wherein said Streptococcus pneumoniae-derived capsular polysaccharide is a Pn-serotype 33F capsular polysaccharide. ### Claim 11 (depends on 1) The glycoconjugate of claim 1, wherein said carrier protein is CRM197. ### Claim 12 (depends on 1) An immunogenic composition comprising a glycoconjugate according to claim 1 and a pharmaceutically acceptable excipient, carrier, or diluent. ### Claim 13 (depends on 12) An immunogenic composition according to claim 12 further comprising an additional antigen. ### Claim 14 (depends on 13) An immunogenic composition according to claim 13, wherein the additional antigen comprises a glycoconjugate of a Streptococcus pneumoniae-derived capsular polysaccharide selected from the group consisting of Pn-serotype 1, 3, 4, 5, 6A, 6B, 7F, 8, 9V, 10A, 11A, 12F, 14, 15B, 18C, 19A, 19F, 22F, 23F and 33F capsular polysaccharides. ### Claim 15 (depends on 14) An immunogenic composition according to claim 14 further comprising at least one adjuvant. ### Claim 16 A glycoconjugate comprising a Streptococcus pneumoniae-derived capsular polysaccharide conjugated to a carrier protein through a (2-((2-oxoethyl)thio)ethyl)carbamate (eTEC) spacer, wherein the polysaccharide is covalently linked to the eTEC spacer through a carbamate linkage, and wherein the carrier protein is covalently linked to the eTEC spacer through an amide linkage, as shown by formula (I): wherein the glycoconjugate comprises at least one covalent linkage between the carrier protein and the polysaccharide for every 4, 10, 15 or 25 saccharide repeat units of the polysaccharide, and wherein the Streptococcus pneumoniae-derived capsular polysaccharide is selected from the group consisting of Pn-serotype 1, 3, 4, 5, 6A, 6B, 7F, 8, 9V, 10A, 11A, 12F, 14, 15B, 18C, 19A, 19F, 22F, 23F and 33F capsular polysaccharides. ### Claim 17 A glycoconjugate comprising a Streptococcus pneumoniae-derived capsular polysaccharide conjugated to a carrier protein through a (2-((2-oxoethyl)thio)ethyl)carbamate (eTEC) spacer, wherein the polysaccharide is covalently linked to the eTEC spacer through a carbamate linkage, and wherein the carrier protein is covalently linked to the eTEC spacer through an amide linkage, as shown by formula (I): wherein the glycoconjugate comprises at least one covalent linkage between the carrier protein and the polysaccharide for every 4, 10, 15 or 25 saccharide repeat units of the polysaccharide, and wherein the Streptococcus pneumoniae-derived capsular polysaccharide is a Pn-serotype 33F capsular polysaccharide. ### Claim 18 (depends on 17) An immunogenic composition comprising a glycoconjugate according to claim 17 and a pharmaceutically acceptable excipient, carrier, or diluent. ### Claim 19 (depends on 18) An immunogenic composition according to claim 18 further comprising an additional antigen. ### Claim 20 (depends on 19) An immunogenic composition according to claim 19, wherein the additional antigen comprises a glycoconjugate of a Streptococcus pneumoniae-derived capsular polysaccharide selected from the group consisting of Pn-serotype 1, 3, 4, 5, 6A, 6B, 7F, 8, 9V, 10A, 11A, 12F, 14, 15B, 18C, 19A, 19F, 22F, and 23F capsular polysaccharides.