CA2495570A1 - Immunostimulatory compositions and methods of stimulating an immune response - Google Patents
Immunostimulatory compositions and methods of stimulating an immune response Download PDFInfo
- Publication number
- CA2495570A1 CA2495570A1 CA002495570A CA2495570A CA2495570A1 CA 2495570 A1 CA2495570 A1 CA 2495570A1 CA 002495570 A CA002495570 A CA 002495570A CA 2495570 A CA2495570 A CA 2495570A CA 2495570 A1 CA2495570 A1 CA 2495570A1
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- Prior art keywords
- alkyl
- amine
- group
- immunostimulatory
- aryl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Links
- 230000003308 immunostimulating effect Effects 0.000 title claims abstract 53
- 239000000203 mixture Substances 0.000 title claims abstract 34
- 230000028993 immune response Effects 0.000 title claims abstract 22
- 238000000034 method Methods 0.000 title claims 27
- 230000004936 stimulating effect Effects 0.000 title claims 5
- 239000003607 modifier Substances 0.000 claims abstract 21
- 230000000890 antigenic effect Effects 0.000 claims abstract 16
- -1 imidazoquinoline amine Chemical class 0.000 claims 45
- 229910052739 hydrogen Inorganic materials 0.000 claims 14
- 239000001257 hydrogen Substances 0.000 claims 14
- 229910052736 halogen Inorganic materials 0.000 claims 12
- 125000001072 heteroaryl group Chemical class 0.000 claims 12
- 210000000612 antigen-presenting cell Anatomy 0.000 claims 11
- 210000000628 antibody-producing cell Anatomy 0.000 claims 9
- 125000001424 substituent group Chemical group 0.000 claims 9
- 125000003118 aryl group Chemical group 0.000 claims 6
- 229940124669 imidazoquinoline Drugs 0.000 claims 6
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000003275 alpha amino acid group Chemical group 0.000 claims 4
- 150000001412 amines Chemical class 0.000 claims 4
- 239000000427 antigen Substances 0.000 claims 4
- 102000036639 antigens Human genes 0.000 claims 4
- 108091007433 antigens Proteins 0.000 claims 4
- 238000004113 cell culture Methods 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 229920001184 polypeptide Polymers 0.000 claims 4
- 102000004196 processed proteins & peptides Human genes 0.000 claims 4
- 108090000765 processed proteins & peptides Proteins 0.000 claims 4
- 229960005486 vaccine Drugs 0.000 claims 4
- 210000001744 T-lymphocyte Anatomy 0.000 claims 3
- 108010060804 Toll-Like Receptor 4 Proteins 0.000 claims 3
- 102000008237 Toll-Like Receptor 6 Human genes 0.000 claims 3
- 108010060826 Toll-Like Receptor 6 Proteins 0.000 claims 3
- 108010060825 Toll-Like Receptor 7 Proteins 0.000 claims 3
- 108010060752 Toll-Like Receptor 8 Proteins 0.000 claims 3
- 102000008228 Toll-like receptor 2 Human genes 0.000 claims 3
- 108010060888 Toll-like receptor 2 Proteins 0.000 claims 3
- 102100039360 Toll-like receptor 4 Human genes 0.000 claims 3
- 102100039390 Toll-like receptor 7 Human genes 0.000 claims 3
- 102100033110 Toll-like receptor 8 Human genes 0.000 claims 3
- 239000000556 agonist Substances 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 230000008878 coupling Effects 0.000 claims 3
- 238000010168 coupling process Methods 0.000 claims 3
- 238000005859 coupling reaction Methods 0.000 claims 3
- 238000009792 diffusion process Methods 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical class 0.000 claims 3
- 150000002431 hydrogen Chemical group 0.000 claims 3
- 125000005647 linker group Chemical group 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- 239000000725 suspension Substances 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 239000002158 endotoxin Substances 0.000 claims 2
- 238000000338 in vitro Methods 0.000 claims 2
- 238000001727 in vivo Methods 0.000 claims 2
- 229920006008 lipopolysaccharide Polymers 0.000 claims 2
- 239000002773 nucleotide Substances 0.000 claims 2
- 125000003729 nucleotide group Chemical group 0.000 claims 2
- 102000004169 proteins and genes Human genes 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 241000894006 Bacteria Species 0.000 claims 1
- 241000233866 Fungi Species 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims 1
- 102000029797 Prion Human genes 0.000 claims 1
- 108091000054 Prion Proteins 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- 241000700605 Viruses Species 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- CTRLRINCMYICJO-UHFFFAOYSA-N phenyl azide Chemical compound [N-]=[N+]=NC1=CC=CC=C1 CTRLRINCMYICJO-UHFFFAOYSA-N 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 claims 1
- 150000003141 primary amines Chemical class 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/39—Medicinal preparations containing antigens or antibodies characterised by the immunostimulating additives, e.g. chemical adjuvants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/385—Haptens or antigens, bound to carriers
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K39/395—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/04—Immunostimulants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/555—Medicinal preparations containing antigens or antibodies characterised by a specific combination antigen/adjuvant
- A61K2039/55511—Organic adjuvants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/60—Medicinal preparations containing antigens or antibodies characteristics by the carrier linked to the antigen
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Abstract
The present invention provides immunostimulatory compositions that include an immune response modifier portion paired with an antigenic portion.
Claims (56)
1. An immunostimulatory composition comprising:
an immune response modifier portion paired with an antigenic portion.
an immune response modifier portion paired with an antigenic portion.
2. The immunostimulatory composition of claim 1 wherein the immune response modifier portion is an agonist of Toll-like receptor 2, Toll-like receptor 4, Toll-like receptor 6, Toll-like receptor 7, or Toll-like receptor 8.
3. The immunostimulatory composition of claim 1 wherein the immune response modifier portion comprises an imidazoquinoline amine; a tetrahydroimidazoquinoline amine;
an imidazopyridine amine; an aryl ether-substituted imidazopyridine amine; a 1,2-bridged imidazoquinoline amine; a 6,7-fused cycloalkylimidazopyridine amine; an imidazonaphthyridine amine; a tetrahydroimidazonaphthyridine amine; an oxazoloquinoline amine; a thiazoloquinoline amine; an oxazolopyridine amine; a thiazolopyridine amine; an oxazolonaphthyridine amine; or a thiazolonaphthyridine amine.
an imidazopyridine amine; an aryl ether-substituted imidazopyridine amine; a 1,2-bridged imidazoquinoline amine; a 6,7-fused cycloalkylimidazopyridine amine; an imidazonaphthyridine amine; a tetrahydroimidazonaphthyridine amine; an oxazoloquinoline amine; a thiazoloquinoline amine; an oxazolopyridine amine; a thiazolopyridine amine; an oxazolonaphthyridine amine; or a thiazolonaphthyridine amine.
4. The immunostimulatory composition of claim 1 wherein the immune response modifier portion comprises an organic moiety having a molecular weight of less than about 1000 Daltons.
The immunostimulatory composition of claim 1 wherein immune response modifier portion and the antigenic portion are covalently coupled.
6. The immunostimulatory composition of claim 1 wherein the immune response modifier portion and the antigenic portion are paired by a physical or chemical association other than covalent coupling that limits independent diffusion of the immune response modifier portion with respect to the antigenic portion.
7. The immunostimulatory composition of claim 1 wherein the composition comprises a colloidal suspension.
8. The immunostimulatory composition of claim 1 wherein the antigenic portion comprises an amino acid sequence, a nucleotide sequence, a lipopolysaccharide, a prion, a bacterium, a virus, or a fungus.
9. The immunostimulatory composition of claim 8 wherein the amino acid sequence is a polypeptide.
10. The immunostimulatory composition of claim 9 wherein the polypeptide is a protein.
11. The immunostimulatory composition of claim 1 wherein the immune response modifier portion is a compound of the formula:
wherein:
R1 is a linker group;
R2 is selected from the group consisting of:
-hydrogen;
-alkyl;
-alkenyl;
-aryl;
-substituted aryl;
-heteroaryl;
-substituted heteroaryl;
-alkyl-O-alkyl;
-alkyl-S-alkyl;
-alkyl-O-aryl;
-alkyl-S-aryl:
-alkyl-O- alkenyl;
-alkyl-S- alkenyl; and -alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
-OH;
-halogen;
-N(R5)2;
-CO-N(R5)2;
-CS-N(R5)2;
-SO2-N(R5)2;
-NR5-CO-C1-10 alkyl;
-NR5-CS-C1-10 alkyl;
-NR5- SO2-C1-10 alkyl;
-CO-C1-10 alkyl;
-CO-O-C1-10 alkyl;
-N3;
-aryl;
-substituted aryl;
-heteroaryl;
-substituted heteroaryl;
-heterocyclyl;
-substituted heterocyclyl;
-CO-aryl;
-CO-(substituted aryl);
-CO-heteroaryl; and -CO-(substituted heteroaryl);
R3 and R4 are each independently:
-hydrogen;
-halogen;
-alkyl;
-alkenyl;
-O-alkyl;
-S-alkyl; and -N(R5)2;
or when taken together, R3 and R4 form a fused aryl or heteroaryl group that is optionally substituted by one or more substituents selected from the group consisting of;
-halogen;
-alkyl;
-alkenyl;
-O-alkyl;
-S-alkyl; and -N(R5)2;
or when taken together, R3 and R4 form a fused 5 to 7 membered saturated ring, optionally containing one or more heteroatoms and optionally substituted by one or more substituents selected from the group consisting of;
-halogen;
-alkyl;
-alkenyl;
-O-alkyl;
-S-alkyl; and -N(R5)2; and each R5 is independently hydrogen or C1-10 alkyl.
wherein:
R1 is a linker group;
R2 is selected from the group consisting of:
-hydrogen;
-alkyl;
-alkenyl;
-aryl;
-substituted aryl;
-heteroaryl;
-substituted heteroaryl;
-alkyl-O-alkyl;
-alkyl-S-alkyl;
-alkyl-O-aryl;
-alkyl-S-aryl:
-alkyl-O- alkenyl;
-alkyl-S- alkenyl; and -alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
-OH;
-halogen;
-N(R5)2;
-CO-N(R5)2;
-CS-N(R5)2;
-SO2-N(R5)2;
-NR5-CO-C1-10 alkyl;
-NR5-CS-C1-10 alkyl;
-NR5- SO2-C1-10 alkyl;
-CO-C1-10 alkyl;
-CO-O-C1-10 alkyl;
-N3;
-aryl;
-substituted aryl;
-heteroaryl;
-substituted heteroaryl;
-heterocyclyl;
-substituted heterocyclyl;
-CO-aryl;
-CO-(substituted aryl);
-CO-heteroaryl; and -CO-(substituted heteroaryl);
R3 and R4 are each independently:
-hydrogen;
-halogen;
-alkyl;
-alkenyl;
-O-alkyl;
-S-alkyl; and -N(R5)2;
or when taken together, R3 and R4 form a fused aryl or heteroaryl group that is optionally substituted by one or more substituents selected from the group consisting of;
-halogen;
-alkyl;
-alkenyl;
-O-alkyl;
-S-alkyl; and -N(R5)2;
or when taken together, R3 and R4 form a fused 5 to 7 membered saturated ring, optionally containing one or more heteroatoms and optionally substituted by one or more substituents selected from the group consisting of;
-halogen;
-alkyl;
-alkenyl;
-O-alkyl;
-S-alkyl; and -N(R5)2; and each R5 is independently hydrogen or C1-10 alkyl.
12. An immunostimulatory conjugate of the formula:
wherein:
R1 is a linker group;
R2 is selected from the group consisting of:
-hydrogen;
-alkyl;
-alkenyl;
-aryl;
-substituted aryl;
-heteroaryl;
-substituted heteroaryl;
-alkyl-O-alkyl;
-alkyl-S-alkyl;
-alkyl-O-aryl;
-alkyl-S-aryl:
-alkyl-O- alkenyl;
-alkyl-S- alkenyl; and -alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
-OH;
-halogen;
-N(R5)2;
-CO-N(R5)2;
-CS-N(R5)2;
-SO2-N(R5)2;
-NR5-CO-C1-10 alkyl;
-NR5-CS-C1-10 alkyl;
-NR5- SO2-C1-10 alkyl;
-CO-C1-10 alkyl;
-CO-O-C1-10 alkyl;
-N3;
-aryl;
-substituted aryl;
-heteroaryl;
-substituted heteroaryl;
-heterocyclyl;
-substituted heterocyclyl;
-CO-aryl;
-CO-(substituted aryl);
-CO-heteroaryl; and -CO-(substituted heteroaryl);
R3 and R4 are each independently:
-hydrogen;
-halogen;
-alkyl;
-alkenyl;
-O-alkyl;
-S-alkyl; and -N(R5)2;
or when taken together, R3 and R4 form a fused aryl or heteroaryl group that is optionally substituted by one or more substituents selected from the group consisting of;
-halogen;
-alkyl;
-alkenyl;
-O-alkyl;
-S-alkyl; and -N(R5)2;
or when taken together, R3 and R4 form a fused 5 to 7 membered saturated ring, optionally containing one or more heteroatoms and optionally substituted by one or more substituents selected from the group consisting of;
-halogen;
-alkyl;
-alkenyl;
-O-alkyl;
-S-alkyl; and -N(R5)2;
each R5 is independently hydrogen or C1-10 alkyl; and n is 1 to 10; or a pharmaceutically acceptable salt thereof.
wherein:
R1 is a linker group;
R2 is selected from the group consisting of:
-hydrogen;
-alkyl;
-alkenyl;
-aryl;
-substituted aryl;
-heteroaryl;
-substituted heteroaryl;
-alkyl-O-alkyl;
-alkyl-S-alkyl;
-alkyl-O-aryl;
-alkyl-S-aryl:
-alkyl-O- alkenyl;
-alkyl-S- alkenyl; and -alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
-OH;
-halogen;
-N(R5)2;
-CO-N(R5)2;
-CS-N(R5)2;
-SO2-N(R5)2;
-NR5-CO-C1-10 alkyl;
-NR5-CS-C1-10 alkyl;
-NR5- SO2-C1-10 alkyl;
-CO-C1-10 alkyl;
-CO-O-C1-10 alkyl;
-N3;
-aryl;
-substituted aryl;
-heteroaryl;
-substituted heteroaryl;
-heterocyclyl;
-substituted heterocyclyl;
-CO-aryl;
-CO-(substituted aryl);
-CO-heteroaryl; and -CO-(substituted heteroaryl);
R3 and R4 are each independently:
-hydrogen;
-halogen;
-alkyl;
-alkenyl;
-O-alkyl;
-S-alkyl; and -N(R5)2;
or when taken together, R3 and R4 form a fused aryl or heteroaryl group that is optionally substituted by one or more substituents selected from the group consisting of;
-halogen;
-alkyl;
-alkenyl;
-O-alkyl;
-S-alkyl; and -N(R5)2;
or when taken together, R3 and R4 form a fused 5 to 7 membered saturated ring, optionally containing one or more heteroatoms and optionally substituted by one or more substituents selected from the group consisting of;
-halogen;
-alkyl;
-alkenyl;
-O-alkyl;
-S-alkyl; and -N(R5)2;
each R5 is independently hydrogen or C1-10 alkyl; and n is 1 to 10; or a pharmaceutically acceptable salt thereof.
13. The immunostimulatory conjugate of claim 12 wherein R2 is selected from the group consisting of hydrogen, alkyl and alkyl-O-alkyl.
14. The immunostimulatory conjugate of claim 13 wherein R2 is selected from the group consisting of hydrogen, methyl, ethyl, propyl, butyl, cyclopropylmethyl, ethoxymethyl and methoxyethyl.
15. The immunostimulatory conjugate of claim 12 wherein R3 and R4 are taken together to form a benzene ring.
16. The immunostimulatory conjugate of claim 12 wherein R3 and R4 are taken together to form a pyridine ring.
17. The immunostimulatory conjugate of claim 12 wherein R3 and R4 are taken together to form a 6-membered saturated ring.
18. The immunostimulatory conjugate of claim 12 wherein R3 and R4 are taken together to form a 6-membered saturated ring containing a nitrogen atom.
19. The immunostimulatory conjugate of claim 12 wherein R3 and R4 are independently selected from the group consisting of hydrogen and alkyl.
20. The immunostimulatory conjugate of claim 12 wherein R1 has the formula:
-X-Y-Z-wherein X is an alkylene group optionally interrupted by one or more of -O-;
-S(O)0-2-;
-N(R5)-;
-N(R5)-C(O)-;
-N(R5)-S(O2)-;
-N(R5)-C(O)-N(R5)-;
-N(R5)-C(S)-N(R5)-; and -C(O)-N(R5)-;
Y is a bond or is selected from the group consisting of:
-N(R5)-;
-N(R5)-C(O)-;
-N(R5)-C(O)-cyclohexyl-;
-N(R5)-C(O)-phenylene-; and -phenylene-;
Z is the divalent linking group that is formed when the reactive group Z A
covalently couples to the antigen;
Z A is a reactive group that reacts with the antigen to form a covalent bond;
and each R5 is independently hydrogen or C1-10 alkyl.
-X-Y-Z-wherein X is an alkylene group optionally interrupted by one or more of -O-;
-S(O)0-2-;
-N(R5)-;
-N(R5)-C(O)-;
-N(R5)-S(O2)-;
-N(R5)-C(O)-N(R5)-;
-N(R5)-C(S)-N(R5)-; and -C(O)-N(R5)-;
Y is a bond or is selected from the group consisting of:
-N(R5)-;
-N(R5)-C(O)-;
-N(R5)-C(O)-cyclohexyl-;
-N(R5)-C(O)-phenylene-; and -phenylene-;
Z is the divalent linking group that is formed when the reactive group Z A
covalently couples to the antigen;
Z A is a reactive group that reacts with the antigen to form a covalent bond;
and each R5 is independently hydrogen or C1-10 alkyl.
21. The immunostimulatory conjugate of claim 20 wherein Z A is a group that reacts with primary amines.
22. The immunostimulatory conjugate of claim 21 wherein Z A is an N-hydroxysuccinimide ester or an N-hydroxysulfosuccinimide ester.
23. The immunostimulatory conjugate of claim 20 wherein Z A is a group that reacts with a sulfhydryl group.
24. The immunostimulatory conjugate of claim 23 wherein Z A is a maleimide or an iodoacetyl group.
25. The immunostimulatory conjugate of claim 20 wherein Z A is a photoreactive group.
26. The immunostimulatory conjugate of claim 25 wherein Z A is a phenyl azide.
27. The immunostimulatory conjugate of claim 26 wherein Z A is selected from the group consisting of 4-azidophenyl, 2-hydroxy-4-azidophenyl, 2-nitro-4-azidophenyl, and 2-nitro-3-azidophenyl.
28. The immunostimulatory conjugate of claim 20 wherein Z is selected from the group consisting of:
-C(O)-;
-C(O)-CH2-;
wherein R' is hydrogen, hydroxy or nitro.
-C(O)-;
-C(O)-CH2-;
wherein R' is hydrogen, hydroxy or nitro.
29. The immunostimulatory conjugate of claim 12 wherein the antigen comprises an amino acid sequence, a nucleotide sequence or a lipopolysaccharide.
30. The immunostimulatory conjugate of claim 29 wherein the amino acid sequence is a polypeptide.
31. The immunostimulatory conjugate of claim 30 wherein the polypeptide is a protein.
32. A compound of the formula:
wherein:
X is an alkylene group optionally interrupted by one or more of:
-O-;
-S(O)0-2-;
-N(R5)-;
_N(R5)-C(O)-;
_N(R5)_S(O2)-;
-N(R5)-C(O)-N(R5)-;
-N(R5)-C(S)-N(R5)-; and -C(O)-N(R5)-;
Y is a bond or is selected from the group consisting of:
-N(R5)-;
-N(R5)-C(O)-;
-N(R5)-C(O)-cyclohexyl-;
-N(R5)-C(O)-phenylene-; and -phenylene-;
Z A is a reactive group that reacts with the antigen to form a covalent bond;
R2 is selected from the group consisting of:
-hydrogen;
-alkyl;
-alkenyl;
-aryl;
-substituted aryl;
-heteroaryl;
-substituted heteroaryl;
-alkyl-O-alkyl;
-alkyl-S-alkyl;
-alkyl-O-aryl;
-alkyl-S-aryl:
-alkyl-O- alkenyl;
-alkyl-S- alkenyl; and -alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
-OH;
-halogen;
-N(R5)2;
-CO-N(R5)2;
-CS-N(R5)2;
-SO2-N(R5)2;
-NR5-CO-C1-10 alkyl;
-NR5-CS-C1-10 alkyl;
-NR5-SO-C1-10 alkyl;
-CO-C-10 alkyl;
-CO-O-C1 alkyl;
-N3;
-aryl;
-substituted aryl;
-heteroaryl;
-substituted heteroaryl;
-heterocyclyl;
-substituted heterocyclyl;
-CO-aryl;
-CO-(substituted aryl);
-CO-heteroaryl; and -CO-(substituted heteroaryl);
R3 and R4 are each independently:
-hydrogen;
-halogen;
-alkyl;
-alkenyl;
-O-alkyl;
-S-alkyl; and -N(R5)2;
or when taken together, R3 and R4 form a fused aryl or heteroaryl group that is optionally substituted by one or more substituents selected from the group consisting of;
-halogen;
-alkyl;
-alkenyl;
-O-alkyl;
-S-alkyl; and -N(R5)2;
or when taken together, R3 and R4 form a fused 5 to 7 membered saturated ring, optionally containing one or more heteroatoms and optionally substituted by one or more substituents selected from the group consisting of;
-halogen;
-alkyl;
-alkenyl;
-O-alkyl;
-S-alkyl; and -N(R5)2;
each R5 is independently hydrogen or C1-10 alkyl; or a pharmaceutically acceptable salt thereof.
wherein:
X is an alkylene group optionally interrupted by one or more of:
-O-;
-S(O)0-2-;
-N(R5)-;
_N(R5)-C(O)-;
_N(R5)_S(O2)-;
-N(R5)-C(O)-N(R5)-;
-N(R5)-C(S)-N(R5)-; and -C(O)-N(R5)-;
Y is a bond or is selected from the group consisting of:
-N(R5)-;
-N(R5)-C(O)-;
-N(R5)-C(O)-cyclohexyl-;
-N(R5)-C(O)-phenylene-; and -phenylene-;
Z A is a reactive group that reacts with the antigen to form a covalent bond;
R2 is selected from the group consisting of:
-hydrogen;
-alkyl;
-alkenyl;
-aryl;
-substituted aryl;
-heteroaryl;
-substituted heteroaryl;
-alkyl-O-alkyl;
-alkyl-S-alkyl;
-alkyl-O-aryl;
-alkyl-S-aryl:
-alkyl-O- alkenyl;
-alkyl-S- alkenyl; and -alkyl or alkenyl substituted by one or more substituents selected from the group consisting of:
-OH;
-halogen;
-N(R5)2;
-CO-N(R5)2;
-CS-N(R5)2;
-SO2-N(R5)2;
-NR5-CO-C1-10 alkyl;
-NR5-CS-C1-10 alkyl;
-NR5-SO-C1-10 alkyl;
-CO-C-10 alkyl;
-CO-O-C1 alkyl;
-N3;
-aryl;
-substituted aryl;
-heteroaryl;
-substituted heteroaryl;
-heterocyclyl;
-substituted heterocyclyl;
-CO-aryl;
-CO-(substituted aryl);
-CO-heteroaryl; and -CO-(substituted heteroaryl);
R3 and R4 are each independently:
-hydrogen;
-halogen;
-alkyl;
-alkenyl;
-O-alkyl;
-S-alkyl; and -N(R5)2;
or when taken together, R3 and R4 form a fused aryl or heteroaryl group that is optionally substituted by one or more substituents selected from the group consisting of;
-halogen;
-alkyl;
-alkenyl;
-O-alkyl;
-S-alkyl; and -N(R5)2;
or when taken together, R3 and R4 form a fused 5 to 7 membered saturated ring, optionally containing one or more heteroatoms and optionally substituted by one or more substituents selected from the group consisting of;
-halogen;
-alkyl;
-alkenyl;
-O-alkyl;
-S-alkyl; and -N(R5)2;
each R5 is independently hydrogen or C1-10 alkyl; or a pharmaceutically acceptable salt thereof.
33. A method of stimulating T cells of a patient, the method comprising:
a) providing an immunostimulatory composition that comprises an immune response modifier portion paired with an antigenic portion;
b) permitting the immunostimulatory composition to bind to antigen-presenting cells, thereby activating the antigen-presenting cells; and c) permitting the activated antigen-presenting cells to stimulate the patient's T
cells.
a) providing an immunostimulatory composition that comprises an immune response modifier portion paired with an antigenic portion;
b) permitting the immunostimulatory composition to bind to antigen-presenting cells, thereby activating the antigen-presenting cells; and c) permitting the activated antigen-presenting cells to stimulate the patient's T
cells.
34. The method of claim 33 wherein the immune response modifier portion is an agonist of Toll-like receptor 2, Toll-like receptor 4, Toll-like receptor 6, Toll-like receptor 7, or Toll-like receptor 8.
35. The method of claim 33 wherein the immune response modifier portion comprises an imidazoquinoline amine; a tetrahydroimidazoquinoline amine; an imidazopyridine amine; an aryl ether-substituted imidazopyridine amine; a 1,2-bridged imidazoquinoline amine; a 6,7-fused cycloalkylimidazopyridine amine; an imidazonaphthyridine amine; a tetrahydroimidazonaphthyridine amine; an oxazoloquinoline amine; a thiazoloquinoline amine; an oxazolopyridine amine; a thiazolopyridine amine; an oxazolonaphthyridine amine;
or a thiazolonaphthyridine amine.
or a thiazolonaphthyridine amine.
36. The method of claim 33 wherein the immune response modifier portion and the antigenic portion are covalently coupled.
37. The method of claim 33 wherein the immune response modifier portion and the antigenic portion are paired by a chemical or physical association other than covalent coupling that limits independent diffusion of the immune response modifier portion with respect to the antigenic portion.
38. The method of claim 37 wherein the immunostimulatory composition comprises a colloidal suspension.
39. The method of claim 33 wherein the immunostimulatory composition is permitted to bind to the antigen-presenting cells in vitro.
40. The method of claim 39 wherein the step of permitting the immunostimulatory composition to bind to antigen-presenting cells comprises:
a) providing a cell culture comprising antigen-presenting cells; and b) contacting an amount of the immunostimulatory composition effective for stimulating the antigen-presenting cells with the cell culture.
a) providing a cell culture comprising antigen-presenting cells; and b) contacting an amount of the immunostimulatory composition effective for stimulating the antigen-presenting cells with the cell culture.
41. The method of claim 39 wherein the step of permitting the activated antigen-presenting cells to stimulate the patient's T cells comprises injecting the activated antigen-presenting cells into the patient.
42. The method of claim 33 wherein the immunostimulatory composition is permitted to bind to the antigen-presenting cells in vivo.
43. The method of claim 42 wherein the step of permitting the immunostimulatory composition to bind to antigen-presenting cells comprises:
a) providing the immunostimulatory composition as a component of a vaccine;
and b) vaccinating the patient with the vaccine.
a) providing the immunostimulatory composition as a component of a vaccine;
and b) vaccinating the patient with the vaccine.
44. The method of claim 42 wherein the immunostimulatory composition comprises a tumor-specific antigenic portion.
45. A method of stimulating antibody-producing cells, the method comprising:
a) providing an immunostimulatory composition that comprises an immune response modifier portion paired with an antigenic portion; and b) permitting the immunostimulatory composition to bind to the antibody-producing cells.
a) providing an immunostimulatory composition that comprises an immune response modifier portion paired with an antigenic portion; and b) permitting the immunostimulatory composition to bind to the antibody-producing cells.
46. The method of claim 45 wherein the immune response modifier portion comprises an agonist of Toll-like receptor 2, Toll-like receptor 4, Toll-like receptor 6, Toll-like receptor 7, or Toll-like receptor 8.
47. The method of claim 45 wherein the immune response modifier portion comprises an imidazoquinoline amine; a tetrahydroimidazoquinoline amine; an imidazopyridine amine; an aryl ether-substituted imidazopyridine amine; a 1,2-bridged imidazoquinoline amine; a 6,7-fused cycloalkylimidazopyridine amine; an imidazonaphthyridine amine; a tetrahydroimidazonaphthyridine amine; an oxazoloquinoline amine; a thiazoloquinoline amine; an oxazolopyridine amine; a thiazolopyridine amine; an oxazolonaphthyridine amine;
or a thiazolonaphthyridxne amine.
or a thiazolonaphthyridxne amine.
48. The method of claim 45 wherein the immune response modifier portion and the antigenic portion are covalently coupled.
49. The method of claim 45 wherein the immune response modifier portion and the antigenic portion are paired by a chemical or physical association other than covalent coupling that limits independent diffusion of the immune response modifier portion with respect to the antigenic portion.
50. The method of claim 49 wherein the immunostimulatory composition comprises a colloidal suspension.
51. The method of claim 45 wherein the immunostimulatory composition is permitted to bind to the antibody-producing cells in vivo.
52. The method of claim 51 wherein the step of permitting the immunostimulatory composition to bind to antibody-producing cells comprises:
a) providing the immunostimulatory composition as a component of a vaccine;
and b) introducing the vaccine into a patient having antibody-producing cells.
a) providing the immunostimulatory composition as a component of a vaccine;
and b) introducing the vaccine into a patient having antibody-producing cells.
53. The method of claim 51 wherein the immunostimulatory composition comprises a tumor-specific antigenic portion.
54. The method of claim 45 wherein the immunostimulatory composition is permitted to bind to the antibody-producing cells in vitro.
55. The method of claim 54 wherein the step of permitting the immunostimulatory composition to bind to the antibody-stimulating cells comprises:
a) providing a cell culture comprising antibody-producing cells;
b) contacting the cell culture with an amount of the immunostimulatory composition effective for stimulating the antibody-producing cells.
a) providing a cell culture comprising antibody-producing cells;
b) contacting the cell culture with an amount of the immunostimulatory composition effective for stimulating the antibody-producing cells.
56. The method of claim 45 further comprising collecting antibodies produced by the stimulated antibody-producing cells.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US40384602P | 2002-08-15 | 2002-08-15 | |
| US60/403,846 | 2002-08-15 | ||
| PCT/US2003/025523 WO2004032829A2 (en) | 2002-08-15 | 2003-08-14 | Immunostimulatory compositions and methods of stimulating an immune response |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2495570A1 true CA2495570A1 (en) | 2004-04-22 |
| CA2495570C CA2495570C (en) | 2012-12-04 |
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ID=32093749
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2495570A Expired - Fee Related CA2495570C (en) | 2002-08-15 | 2003-08-14 | Immunostimulatory compositions and methods of stimulating an immune response |
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| Country | Link |
|---|---|
| US (1) | US7427629B2 (en) |
| EP (2) | EP1545597B1 (en) |
| JP (2) | JP4860923B2 (en) |
| KR (1) | KR101088615B1 (en) |
| CN (1) | CN1671412B (en) |
| AT (1) | ATE488246T1 (en) |
| AU (1) | AU2003299863B2 (en) |
| BR (1) | BR0313587A (en) |
| CA (1) | CA2495570C (en) |
| DE (1) | DE60335010D1 (en) |
| DK (1) | DK1545597T3 (en) |
| ES (1) | ES2355819T3 (en) |
| MX (1) | MXPA05001647A (en) |
| NZ (1) | NZ538812A (en) |
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| JP4860923B2 (en) | 2012-01-25 |
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