CA2166208A1 - Phosphazene polyelectrolytes as immunoadjuvants - Google Patents
Phosphazene polyelectrolytes as immunoadjuvantsInfo
- Publication number
- CA2166208A1 CA2166208A1 CA002166208A CA2166208A CA2166208A1 CA 2166208 A1 CA2166208 A1 CA 2166208A1 CA 002166208 A CA002166208 A CA 002166208A CA 2166208 A CA2166208 A CA 2166208A CA 2166208 A1 CA2166208 A1 CA 2166208A1
- Authority
- CA
- Canada
- Prior art keywords
- aliphatic
- composition
- group
- antigen
- polyphosphazene
- 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.)
- Granted
Links
- 229920000867 polyelectrolyte Polymers 0.000 title claims abstract 16
- GKTNLYAAZKKMTQ-UHFFFAOYSA-N n-[bis(dimethylamino)phosphinimyl]-n-methylmethanamine Chemical compound CN(C)P(=N)(N(C)C)N(C)C GKTNLYAAZKKMTQ-UHFFFAOYSA-N 0.000 title claims 3
- 230000001571 immunoadjuvant effect Effects 0.000 title abstract 2
- 239000000568 immunological adjuvant Substances 0.000 title abstract 2
- 229920002627 poly(phosphazenes) Polymers 0.000 claims abstract 16
- 230000007062 hydrolysis Effects 0.000 claims abstract 9
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract 9
- 229920000642 polymer Polymers 0.000 claims abstract 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims 21
- 239000000427 antigen Substances 0.000 claims 12
- 102000036639 antigens Human genes 0.000 claims 12
- 108091007433 antigens Proteins 0.000 claims 12
- 125000001931 aliphatic group Chemical group 0.000 claims 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- 102000004169 proteins and genes Human genes 0.000 claims 6
- 108090000623 proteins and genes Proteins 0.000 claims 6
- -1 amino acid ester Chemical class 0.000 claims 5
- 241000725303 Human immunodeficiency virus Species 0.000 claims 4
- 150000001875 compounds Chemical class 0.000 claims 4
- 241001465754 Metazoa Species 0.000 claims 3
- 150000001735 carboxylic acids Chemical class 0.000 claims 3
- 150000001768 cations Chemical class 0.000 claims 3
- 150000004676 glycans Chemical class 0.000 claims 3
- 229920001282 polysaccharide Polymers 0.000 claims 3
- 239000005017 polysaccharide Substances 0.000 claims 3
- 241000894006 Bacteria Species 0.000 claims 2
- 108010077805 Bacterial Proteins Proteins 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 229930186217 Glycolipid Natural products 0.000 claims 2
- 102000003886 Glycoproteins Human genes 0.000 claims 2
- 108090000288 Glycoproteins Proteins 0.000 claims 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 2
- 229910018830 PO3H Inorganic materials 0.000 claims 2
- 229910006069 SO3H Inorganic materials 0.000 claims 2
- 241000700605 Viruses Species 0.000 claims 2
- 125000004947 alkyl aryl amino group Chemical group 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 150000001413 amino acids Chemical class 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 230000001580 bacterial effect Effects 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000004986 diarylamino group Chemical group 0.000 claims 2
- 239000002158 endotoxin Substances 0.000 claims 2
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 claims 2
- 208000002672 hepatitis B Diseases 0.000 claims 2
- 125000004404 heteroalkyl group Chemical group 0.000 claims 2
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 206010022000 influenza Diseases 0.000 claims 2
- 210000003563 lymphoid tissue Anatomy 0.000 claims 2
- 102000039446 nucleic acids Human genes 0.000 claims 2
- 108020004707 nucleic acids Proteins 0.000 claims 2
- 150000007523 nucleic acids Chemical class 0.000 claims 2
- 239000002245 particle Substances 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 229920002873 Polyethylenimine Polymers 0.000 claims 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims 1
- 229910052782 aluminium Inorganic materials 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- 229910052788 barium Inorganic materials 0.000 claims 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 1
- 229910052791 calcium Inorganic materials 0.000 claims 1
- 239000011575 calcium Substances 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 230000028993 immune response Effects 0.000 claims 1
- 229910052742 iron Inorganic materials 0.000 claims 1
- 229920006008 lipopolysaccharide Polymers 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- 229920001308 poly(aminoacid) Polymers 0.000 claims 1
- 210000000664 rectum Anatomy 0.000 claims 1
- 210000002345 respiratory system Anatomy 0.000 claims 1
- 229910052712 strontium Inorganic materials 0.000 claims 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 claims 1
- 229910052718 tin Inorganic materials 0.000 claims 1
- 239000011135 tin Substances 0.000 claims 1
- 229960005486 vaccine Drugs 0.000 claims 1
- 229910052725 zinc Inorganic materials 0.000 claims 1
- 239000011701 zinc Substances 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 abstract 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 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
- A61K39/385—Haptens or antigens, bound to carriers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/02—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing phosphorus
- C08G79/025—Polyphosphazenes
-
- 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
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1629—Organic macromolecular compounds
- A61K9/1641—Organic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, poloxamers
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K39/00—Medicinal preparations containing antigens or antibodies
- A61K2039/54—Medicinal preparations containing antigens or antibodies characterised by the route of administration
- A61K2039/541—Mucosal route
-
- 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
- A61K2039/55555—Liposomes; Vesicles, e.g. nanoparticles; Spheres, e.g. nanospheres; Polymers
-
- 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
An immunoadjuvant soluble polyphosphazene polyelectrolyte is disclosed. In one embodiment, the polymeric adjuvant is a poly(organophosphazene) with (i) ionized or ionizable pendant groups that contain, for example, carboxylic acid, sulfonic acid, or hydroxyl moieties, and (ii) pendant groups that are susceptible to hydrolysis under the conditions of use, to impart biodegradability to the polymer.
Claims (37)
1. A vaccine composition comprising a watersoluble polyphosphazene polyelectrolyte in combination with an antigen.
2. The composition of claim 1 wherein the polyphosphazene polyelectrolyte is of the formula wherein A and B can vary independently in the polymer, and can be:
(i) a group that is susceptible to hydrolysis under the conditions of use; or (ii) a group that is not susceptible to hydrolysis under the conditions of use selected from the group consisting of aliphatic, aryl, aralkyl, alkaryl, carboxylic acid, heteroaromatic, heteroalkyl, (aliphatic)amino-, heteroaralkyl, di(aliphatic)aminoarylamino-, diarylamino-, alkylarylamino-, -oxyaryl, -oxyphenylCO2H, -oxyphenylSO3H, -oxyphenylhydroxyl, -oxyphenylPO3H, -oxyaliphatic, -oxyalkyl, -oxy(aliphatic)CO2H, -oxy(aliphatic)SO3H, -oxy(aliphatic)PO3H, -oxy(aliphatic)hydroxyl, -oxyalkaryl, -oxyaralkyl, -thioaryl, -thioaliphatic, -thioalkaryl, thioaralkyl, or -NHC(O)O-(aryl or aliphatic), -O-[(CH2)xO]y-(CH2)xNH2 -O-[(CH2)xO]y(CH2)xNH(CH2)xSO3H, and -O-[(CH2)xO]y-(aryl or aliphatic), wherein x is 1-8 and y is an integer of 1 to 20;
and wherein n is an interger.
(i) a group that is susceptible to hydrolysis under the conditions of use; or (ii) a group that is not susceptible to hydrolysis under the conditions of use selected from the group consisting of aliphatic, aryl, aralkyl, alkaryl, carboxylic acid, heteroaromatic, heteroalkyl, (aliphatic)amino-, heteroaralkyl, di(aliphatic)aminoarylamino-, diarylamino-, alkylarylamino-, -oxyaryl, -oxyphenylCO2H, -oxyphenylSO3H, -oxyphenylhydroxyl, -oxyphenylPO3H, -oxyaliphatic, -oxyalkyl, -oxy(aliphatic)CO2H, -oxy(aliphatic)SO3H, -oxy(aliphatic)PO3H, -oxy(aliphatic)hydroxyl, -oxyalkaryl, -oxyaralkyl, -thioaryl, -thioaliphatic, -thioalkaryl, thioaralkyl, or -NHC(O)O-(aryl or aliphatic), -O-[(CH2)xO]y-(CH2)xNH2 -O-[(CH2)xO]y(CH2)xNH(CH2)xSO3H, and -O-[(CH2)xO]y-(aryl or aliphatic), wherein x is 1-8 and y is an integer of 1 to 20;
and wherein n is an interger.
3. The composition of claim 2, wherein the polymer contains at least 10 percent or more of repeating units that are not susceptible to hydrolysis under the conditions of use.
4. The composition of claim 2, wherein the polymer contains at least 90 percent or more of repeating units that are not susceptible to hydrolysis under the conditions of use.
5. The composition of claim 2, wherein the hydrolyzable groups are independently selected from the group consisting of chlorine, amino acid or amino acid ester (bound through the amino group), imidazole, glycerol, and glucosyl.
6. The composition of claim 1 wherein the polyphosphazene polyelectrolyte is biodegradable.
7. The composition of claim 1 wherein the polyphosphazene is mixed with the antigen.
8. The composition of claim 8 wherein the polyphosphazene polyelectrolyte is cross-linked with a multivalent cation.
9. The composition of claim 8 wherein the multivalent cation is selected from the group consisting of calcium, copper, aluminum, magnesium, strontium, barium, tin, zinc, iron, poly(amino acid), poly(ethyleneimine), poly(vinylamine) and polysaccharides.
10. The composition of claim 1 wherein the antigen is selected from the group consisting of a compound derived from a cell, bacteria, or virus particle, or portion thereof, wherein the compound is selected from the group consisting of proteins, peptides, polysaccharides, glycoproteins, glycolipids, nucleic acid, or combinations thereof.
11. The composition of claim 10 wherein the antigen is selected from the group consisting of influenza proteins, human immunodeficiency virus (HIV) proteins, hepatitis B
proteins, bacterial proteins and bacterial lipopoly-saccharides.
proteins, bacterial proteins and bacterial lipopoly-saccharides.
12. The composition of claim 1 wherein the polyphosphazene polyelectrolyte is covalently conjugated with the antigen.
13. The composition of claim 2 wherein the polypphosphazene polyelectrolyte is a phosphazene that has acidic side chains selected from the group consisting of carboxylic acid, sulfonic acid, and hydroxyl groups.
14. The composition of claim 10 wherein the phosphazene polyelectrolyte is biodegradable.
15. The composition of claim 1 for oral delivery.
16. The composition of claim 1 for delivery to the nasal associated lymphoid tissue.
17. The composition of claim 1 for delivery to therectum.
18. The composition of claim 1 for delivery to the
19. A method of causing an immune response in an animal comprising the steps of administering to the animal an antigen in combination with a water-soluble polyphosphazene polyelectrolyte.
20. The method of claim 19, wherein the antigen is conjugated with the polyphosphazene polyelectrolyte.
21. The method of claim 19 wherein the antigen and polyphosphazene are administered separately to proximate sites.
22. The method of claim 19 wherein the antigen and polyphosphazene are first combined and the combination is administered to the animal.
23. The method of claim 19 wherein the method of administration is parenteral.
24. The method of claim 19 wherein the method of administration is oral.
25. The method of claim 19 wherein the polyphosphazene polyelectrolyte is of the formula wherein A and B can vary independently in the polymer, and can be:
(i) a group that is susceptible to hydrolysis under the conditions of use; or (ii) a group that is not susceptible to hydrolysis under the conditions of use selected from the group consisting of aliphatic, aryl, aralkyl, alkaryl, carboxylic acid, heteroaromatic, heteroalkyl, (aliphatic)amino-, heteroaralkyl, di(aliphatic)aminoarylamino-, diarylamino-, alkylarylamino-, -oxyaryl, -oxyphenylCO2H, -oxyphenylSO3H, -oxyphenylhydroxyl, -oxyphenylPO3H, -oxyaliphatic, -oxyalkyl, -oxy(aliphatic)CO2H, -oxy(aliphatic)SO3H, -oxy(aliphatic)PO3H, -oxy(aliphatic)hydroxyl, -oxyalkaryl, -oxyaralkyl, -thioaryl, -thioaliphatic, -thioalkaryl, thioaralkyl, -NHC(O)O-(aryl or aliphatic), -O-[(CH2)xO]y-CH2) -O-[(CH2)xO]yCH2)xNH(CH2)xSO3H, or -O-[(CH2)xO]y-(aryl or aliphatic), wherein x is 1-8 and y wherein n is an integer.
(i) a group that is susceptible to hydrolysis under the conditions of use; or (ii) a group that is not susceptible to hydrolysis under the conditions of use selected from the group consisting of aliphatic, aryl, aralkyl, alkaryl, carboxylic acid, heteroaromatic, heteroalkyl, (aliphatic)amino-, heteroaralkyl, di(aliphatic)aminoarylamino-, diarylamino-, alkylarylamino-, -oxyaryl, -oxyphenylCO2H, -oxyphenylSO3H, -oxyphenylhydroxyl, -oxyphenylPO3H, -oxyaliphatic, -oxyalkyl, -oxy(aliphatic)CO2H, -oxy(aliphatic)SO3H, -oxy(aliphatic)PO3H, -oxy(aliphatic)hydroxyl, -oxyalkaryl, -oxyaralkyl, -thioaryl, -thioaliphatic, -thioalkaryl, thioaralkyl, -NHC(O)O-(aryl or aliphatic), -O-[(CH2)xO]y-CH2) -O-[(CH2)xO]yCH2)xNH(CH2)xSO3H, or -O-[(CH2)xO]y-(aryl or aliphatic), wherein x is 1-8 and y wherein n is an integer.
26. The method of claim 25, wherein the polymer contains at least 10 percent or more of repeating units that are not susceptible to hydrolysis under the conditions of use.
27. The method of claim 25, wherein the polymer contains at least 90 percent or more of repeating units 'hat are not susceptible to hydrolysis under the conditions of use.
28. The method of claim 19 wherein the polyphosphazene polyelectrolyte is biodegradable.
29. The method of claim 28 wherein the polyphosphazene polyelectrolyte contains hydrolyzable side chains selected from the group consisting of amino acid, amino acid ester, chlorine, imidazole, glycerol, and glucosyl.
30. The method of claim 19 wherein the polyphosphazene polyelectrolyte is cross-linked by a multivalent cation.
31. The method of claim 19 wherein the polyphosphazene polyelectrolyte is physically mixed with the antigen.
32. The method of claim 19 wherein the antigen is selected from the group consisting of a compound derived from a cell, bacteria, or virus particle, or portion thereof, wherein the compound is selected from the group consisting of proteins, peptides, polysaccharides, glycoproteins, glycolipids, nucleic acid, or combinations thereof.
33. The method of claim 32 wherein the antigen is selected from the group consisting of influenza proteins, human immunodeficiency virus (HIV) proteins, hepatitis B
proteins, bacterial proteins and bacterial lipopolysaccharides.
proteins, bacterial proteins and bacterial lipopolysaccharides.
34. The method of claim 19 for oral delivery.
35. The method of claim 19 for delivery to the nasal associated lymphoid tissue.
36. The method of claim 19 for delivery to the respiratory tract.
37. The method of claim 19 for delivery to the rectum.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/090,841 | 1993-07-12 | ||
US08/090,841 US5562909A (en) | 1993-07-12 | 1993-07-12 | Phosphazene polyelectrolytes as immunoadjuvants |
PCT/US1994/007665 WO1995002415A1 (en) | 1993-07-12 | 1994-07-08 | Phosphazene polyelectrolytes as immunoadjuvants |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2166208A1 true CA2166208A1 (en) | 1995-01-26 |
CA2166208C CA2166208C (en) | 2010-04-20 |
Family
ID=22224581
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA2166208A Expired - Fee Related CA2166208C (en) | 1993-07-12 | 1994-07-08 | Phosphazene polyelectrolytes as immunoadjuvants |
Country Status (16)
Country | Link |
---|---|
US (3) | US5562909A (en) |
EP (1) | EP0710117B1 (en) |
JP (1) | JPH09500629A (en) |
KR (2) | KR100352336B1 (en) |
CN (1) | CN1134265C (en) |
AT (1) | ATE207505T1 (en) |
AU (1) | AU691824B2 (en) |
BR (1) | BR9407051A (en) |
CA (1) | CA2166208C (en) |
DE (1) | DE69428795T2 (en) |
DK (1) | DK0710117T3 (en) |
ES (1) | ES2166376T3 (en) |
NZ (1) | NZ269396A (en) |
PT (1) | PT710117E (en) |
SG (1) | SG46659A1 (en) |
WO (2) | WO1995002415A1 (en) |
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US5643578A (en) * | 1992-03-23 | 1997-07-01 | University Of Massachusetts Medical Center | Immunization by inoculation of DNA transcription unit |
US5855895A (en) * | 1995-06-07 | 1999-01-05 | Virus Research Institute | Polyphosphazene polyelectrolyte immunoadjuvants |
AU738698B2 (en) * | 1994-07-08 | 2001-09-27 | Avant Immunotherapeutics, Inc. | Polyphosphazene polyelectrolyte immunoadjuvants |
FR2732605B1 (en) * | 1995-04-07 | 1997-05-16 | Pasteur Merieux Serums Vacc | COMPOSITION FOR INDUCING MUCOSAL IMMUNE RESPONSE |
US6428771B1 (en) * | 1995-05-15 | 2002-08-06 | Pharmaceutical Discovery Corporation | Method for drug delivery to the pulmonary system |
US5891444A (en) * | 1995-06-07 | 1999-04-06 | Virus Research Institute, Inc. | HIV-1 prophylactic composition and method |
US5900238A (en) * | 1995-07-27 | 1999-05-04 | Immunex Corporation | Vaccine delivery system |
US5914231A (en) * | 1995-08-17 | 1999-06-22 | Universiteit Utrecht Introgene B.V. | Poly(organo)phosphazenes for use in synthetic transfection systems |
EP0965336A1 (en) * | 1995-11-09 | 1999-12-22 | Microbiological Research Authority | Microencapsulated DNA for gene therapy |
US6126964A (en) * | 1996-01-04 | 2000-10-03 | Mirus Corporation | Process of making a compound by forming a polymer from a template drug |
US5898062A (en) * | 1996-04-10 | 1999-04-27 | The Penn State Research Foundation | Poly (organophosphazene) hydrogels |
US5807757A (en) * | 1996-07-02 | 1998-09-15 | Virus Research Institute, Inc. | Preparation of ionically cross-linked polyphosphazene microspheresy by coacervation |
US6303300B1 (en) * | 1996-08-16 | 2001-10-16 | Introgen B.V. | Poly (organo) phosphazenes for use in synthetic transfection systems |
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US6077662A (en) * | 1996-11-27 | 2000-06-20 | Emory University | Virus-like particles, methods and immunogenic compositions |
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US6077916A (en) * | 1997-06-04 | 2000-06-20 | The Penn State Research Foundation | Biodegradable mixtures of polyphoshazene and other polymers |
US5760271A (en) * | 1997-08-18 | 1998-06-02 | Virus Research Institute, Inc. | Production of polyorganophosphazenes |
WO1999009956A1 (en) * | 1997-08-29 | 1999-03-04 | Corixa Corporation | Rapid release encapsulated bioactive agents for inducing or potentiating an immune response and methods of using thereof |
US5958414A (en) * | 1997-09-03 | 1999-09-28 | Heska Corporation | Composition to protect a mammal against Bartonella henselae infection |
US6726934B1 (en) | 1997-10-09 | 2004-04-27 | Vanderbilt University | Micro-particulate and nano-particulate polymeric delivery system |
EP1021168A4 (en) * | 1997-10-09 | 2006-08-30 | Univ Vanderbilt | Micro-particulate and nano-particulate polymeric delivery system |
US6969520B2 (en) | 1997-10-20 | 2005-11-29 | Acambis Inc. | Active immunization against clostridium difficile disease |
DE69829400T2 (en) | 1997-10-20 | 2006-04-13 | Acambis, Inc., Cambridge | PASSIVE IMMUNIZATION AGAINST CLOSTRIDIUM DIFFICILE DISEASE |
US6207171B1 (en) * | 1998-03-27 | 2001-03-27 | Avant Immunotherapeutics, Inc. | Polyphosphazene microspheres |
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US6506385B1 (en) | 1998-04-17 | 2003-01-14 | Embrex, Inc. | Live vaccines and methods of treatment therewith |
WO1999058134A1 (en) * | 1998-05-11 | 1999-11-18 | Purdue Research Foundation | Methods and compositions for nucleic acid delivery |
US6368625B1 (en) | 1998-08-12 | 2002-04-09 | Cima Labs Inc. | Orally disintegrable tablet forming a viscous slurry |
US7087236B1 (en) * | 1998-09-01 | 2006-08-08 | Merrion Research I Limited | Method for inducing a cell-mediated immune response and improved parenteral vaccine formulations thereof |
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1994
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- 1994-07-08 NZ NZ269396A patent/NZ269396A/en not_active IP Right Cessation
- 1994-07-08 CA CA2166208A patent/CA2166208C/en not_active Expired - Fee Related
- 1994-07-08 AT AT94923378T patent/ATE207505T1/en active
- 1994-07-08 SG SG1996007424A patent/SG46659A1/en unknown
- 1994-07-08 KR KR1019960700227A patent/KR100352336B1/en not_active IP Right Cessation
- 1994-07-08 DK DK94923378T patent/DK0710117T3/en active
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- 1994-07-08 AU AU73261/94A patent/AU691824B2/en not_active Ceased
- 1994-07-08 BR BR9407051A patent/BR9407051A/en not_active Application Discontinuation
- 1994-07-08 PT PT94923378T patent/PT710117E/en unknown
- 1994-07-08 ES ES94923378T patent/ES2166376T3/en not_active Expired - Lifetime
- 1994-07-08 CN CNB94193067XA patent/CN1134265C/en not_active Expired - Fee Related
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PT710117E (en) | 2002-04-29 |
NZ269396A (en) | 1999-09-29 |
WO1995002628A1 (en) | 1995-01-26 |
WO1995002415A1 (en) | 1995-01-26 |
ES2166376T3 (en) | 2002-04-16 |
KR960703617A (en) | 1996-08-31 |
KR100353496B1 (en) | 2003-03-03 |
DE69428795D1 (en) | 2001-11-29 |
CA2166208C (en) | 2010-04-20 |
CN1128954A (en) | 1996-08-14 |
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