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US 2007/0196384 A1Published application
Novel glycolipid adjuvant compositions
AssigneeZoetis LLC
InventorsRamasamy Mannan, Paul Dominowski, Sangita Mediratta
Life of this patent
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Abstract
This invention relates to compositions and methods of preparing stable adjuvant diluent stock solutions and final adjuvant solutions comprising glycolipids, weak acids, alcohols, nonionic surfactants and buffers.
Claims19
A composition comprising:
- a) a glycolipid of Formula I;
- wherein Formula I is
- wherein
- R1 and R2 are independently hydrogen, or a saturated alkyl radical having up to 20 carbon atoms;
- X is —CH2—, —O— or —NH—;
- R2 is hydrogen, or a saturated or unsaturated alkyl radical having up to 20 carbon atoms;
- R3, R4, and R5 are independently hydrogen, —SO42−, —PO42−, —COC1-10alkyl;
- R6 is L-alanyl, L-alpha-aminobutyl, L-arginyl, L-asparginyl, L-aspartyl, L-cysteinyl, L-glutamyl, L-glycyl, L-histidyl, L-hydroxypropyl, L-isoleucyl, L-leucyl, L-lysyl, L-methionyl, L-ornithinyl, L-phenyalany, L-prolyl, L-seryl, L-threonyl, L-tyrosyl, L-tryptophanyl, and L-valyl or their D-isomers;
- in a salt form, where the salt form is derived from a weak acid,
- b) an alcohol, wherein the alcohol is HO—C1-3 alkyl;
- c) a weak acid, wherein the weak acid is, 1) in molar excess with reference to the glycolipid content, and 2) any acid having a pKa (the −log of the Ka) value of between 1.0 and 9.5 using standard tables or values;
- d) a non-ionic surfactant, where the non-ionic surfactant is an agent that reduces the surface tension of the material it is dissolved in and has a component that is hydrophobic and another component that is hydrophilic.
9 more elements
A composition comprising:
- a) a glycolipid of Formula I;
- wherein Formula I is
- wherein
- R1 and R2 are independently hydrogen, or a saturated alkyl radical having up to 20 carbon atoms;
- X is —CH2—, —O— or —NH—;
- R3, R4, and R5 are independently hydrogen, —SO42−, —PO42−, —COC1-10alkyl;
- R6 is L-alanyl, L-alpha-aminobutyl, L-arginyl, L-asparginyl, L-aspartyl, L-cysteinyl, L-glutamyl, L-glycyl, L-histidyl, L-hydroxypropyl, L-isoleucyl, L-leucyl, L-lysyl, L-methionyl, L-ornithinyl, L-phenyalany, L-prolyl, L-seryl, L-threonyl, L-tyrosyl, L-tryptophanyl, and L-valyl or their D-isomers;
- in a salt form, where the salt form is derived from a weak acid,
- b) an alcohol, wherein the alcohol is HO—C1-3 alkyl;
- c) a weak acid, wherein the weak acid is 1) in molar excess with reference to the glycolipid content, and 2) any acid having a pKa (the −log of the Ka) values of between about 1.0 and about 9.5 using standard tables or values;
- d) a non-ionic surfactant, where the non-ionic surfactant is an agent that reduces the surface tension of the material it is dissolved in and has a component that is hydrophobic and another component that is hydrophilic;
- and
- e) an aqueous buffer, wherein the suitable buffer is suitable for vaccine use and can maintain the pH of the other ingredients within a pH range of about 6 to about 8, with the proviso that not more than 50 mM NaCl is used.
10 more elements
A composition comprising:
- a) N-(2-deoxy-2-L-leucylamino-β-D-glucopyranosyl)-N-octadecyldodecanamide acetate, having a structure of Formula III:
- b) ethanol;
- c) acetic acid;
- d) non-ionic surfactant, selected from;
- Sorbitan monolaurate, Sorbitane monopalmitate, Sorbitane monostearate, Sorbitane tristearate, Sorbitane monooleate, Sorbitane trioleate, Polyoxyethylensorbitan monolaurate, Polyoxyethylensorbitan monopalmitate, Polyoxyethylensorbitan monosterate, Polyoxyethylensorbitan monooleate, Polyoxyethylensorbitan trioleate.
- e) an aqueous buffer, where the pH of the solution is adjusted to a relatively constant pH in an aqueous buffered solution of between about 6 and about 7, and the buffer is the following;
- 1) 2-(N-morpholino)ethanesulfonic acid (also known as MES),
- 2) 3-N-morpholino)propanesulfonic acid (also known as MOPS),
- 3) n-[tris (hydroxymethyl]-2-aminoethanesulfonic acid (also known as TES),
- 4) 4-(2-hydroxyethyl)piperazine-1-ethanesulfonic acid (also known as HEPES), and
- 5) [tris(hydroxymethyl)methyl]glycine (also TRIS),
- or any combination thereof,
- with the proviso that not more than 15 mMN NaCl is used and;
- 6) an antigen consisting essentially of modified live bovine herpes virus, modified live bovine respiratory synctial virus, and modified live parainfluenza virus 3.
11 more elements
A process for the preparation of a composition, comprising mixing together the following:
- A) a glycolipid of Formula l;
- B) an alcohol, wherein the alcohol is HCO—C1-3alkyl;
- C) a weak acid, wherein the amount of weak acid is in molar excess with reference to the glycolipid content;
- and
- D) a non-ionic surfactant.
2 more elements
A process for the preparation of a composition, comprising mixing together the following:
- A) a glycolipid of Formula I;
- B) an alcohol, wherein the alcohol is HO—C1-3alkyl;
- C) a weak acid, wherein the amount of weak acid is in molar excess with reference to the glycolipid content;
- D) a non-ionic surfactant;
- and then adding,
- E) a suitable buffer.
3 more elements
Dependencies are inferred from the claim text.