US2004063647A1PendingUtilityA1
Novel amphipathic aldehydes and their use as adjuvants and immunoeffectors
Est. expiryMar 17, 2020(expired)· nominal 20-yr term from priority
Inventors:David A. Johnson
A61P 7/06A61P 37/02A61P 37/08A61P 5/40A61P 3/10A61P 5/14A61P 25/00A61P 35/02A61P 31/04A61P 25/24A61P 31/12A61P 35/00A61P 25/18A61P 31/00A61P 25/28A61P 29/00A61P 17/00A61P 19/02A61P 13/12C07C 65/30A61P 21/04A61P 1/02A61P 15/00A61P 1/14A61P 1/04C07C 69/76A61P 21/00A61P 17/14A61P 1/16
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Claims
Abstract
This invention relates to novel aldehyde containing compounds and their uses as adjuvants and immunoeffectors.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A compound, having the formula:
wherein, R is hydrogen or —C(O)H; R 1 is a member selected from the group consisting of hydrogen, a substituted C 1-20 alkyl group, an unsubstituted C 1-20 alkyl group, a saccharyl group, and a group represented by the formula —(O)—[C(R 3 )(R 4 )] n —COOH,
wherein each R 3 and R 4 independently is a member selected from the group consisting of hydrogen and a substituted C 1-10 alkyl group, an unsubstituted C 1-10 alkyl group; and n is a number from 1 to 5; R 2 is a member selected from the group consisting of hydrogen, a substituted C 1-20 alkyl group, an unsubstituted C 1-20 alkyl group, and a group represented by the formula —(CH 2 ) m CH(OH)(CH 2 ) p OR 5 ,
wherein m and p are independently 1 or 2, and R 5 is a substituted C 2-20 alkyl group, or an unsubstituted C 2-20 alkyl group, or a group represented by the formula
wherein j is 1-5, and R 6 and R 7 are independently selected from the group consisting of hydrogen, a substituted C 1-20 alkyl group, and an unsubstituted C 1-20 alkyl group; or a pharmacologically acceptable salt thereof.
2 . The compound of claim 1 wherein the saccharyl group is a monoor disaccharide.
3 . The compound of claim 1 wherein the saccharyl group is a glucuronic acid group.
4 . The compound of claim 1 wherein R, R 1 , and R 2 are hydrogens.
5 . The compound of claim 1 wherein R is hydrogen; R 1 is a saccharyl group, wherein the saccharyl group is a glucuronic acid group; and R 2 is hydrogen.
6 . The compound of claim 5 wherein the glucuronic acid group is a β-D-glucuronic acid group.
7 . The compound of claim 1 wherein R is hydrogen; R 1 is represented by the formula —C(O)—[C(R 3 )(R 4 )] n —COOH wherein R 3 and R 4 are hydrogens and n is 2; and R 2 is hydrogen.
8 . The compound of claim 1 wherein R is hydrogen; R 1 is a saccharyl group, wherein the saccharyl group is a glucuronic acid group; and R 2 is (CH 2 ) m CH(OH)(CH 2 ) m OR 5 , wherein m is 1, and R 5 is a substituted C 2-20 acyl group, or an unsubstituted C 2-20 acyl group.
9 . The compound of claim 8 wherein (CH 2 ) m CH(OH)(CH 2 ) m OR 5 is a 1-O-acyl-sn-glyceryl group.
10 . The compound of claim 9 wherein the acyl group is a member selected from the group consisting of an acetyl group, an octanoyl group, and a tetradecanoyl group.
11 . The compound of claim 1 wherein R is hydrogen; R 1 is a saccharyl group, wherein the saccharyl group is a glucuronic acid group; and R 2 is a group represented by the formula
wherein j is 1; R 6 is a substituted C 1-20 alkyl group, or an unsubstituted C 1-20 alkyl group; and R 7 is a substituted C 1-20 alkyl group, or an unsubstituted C 1-20 alkyl group.
12 . The compound of claim 11 wherein R 7 is a substituted C 11 alkyl group, or an unsubstituted C 11 alkyl group.
13 . The compound of claim 1 , wherein R 1 is an alkyl group having the formula —(CH 2 ) x COOR 8 , wherein R 8 is hydrogen, a substituted C 1-20 alkyl group, or an unsubstituted C 1-20 alkyl group, wherein X is an integer from 1 to 7.
14 . The compound of claim 13 , wherein X is an integer from 2 to 4.
15 . A liposome vesicle comprising the compound of claim 1 .
16 . A compound comprising an antigen covalently linked to the compound of claim 1 .
17 . A vaccine composition comprising the compound of claim 16 .
18 . A vaccine composition comprising an antigen and the compound of claim 1 .
19 . The vaccine composition of claim 18 wherein the antigen is a bacterial antigen.
20 . The vaccine composition of claim 18 wherein the antigen is a viral antigen.
21 . The vaccine composition of claim 18 wherein the antigen is a tumor associated antigen.
22 . The vaccine composition of claim 18 wherein the antigen is a self-antigen.
23 . An adjuvant composition for potentiating the immunogenicity of an antigen, comprising a suspension of water or an aqueous solution, wherein said suspension or solution comprises the compound of claim 1 .
24 . The adjuvant composition of claim 23 wherein the suspension is an oil-in-water emulsion.
25 . The adjuvant composition of claim 21 wherein the suspension is a water-in-oil emulsion.
26 . The adjuvant composition of claim 23 wherein the suspension is a micellar dispersion comprising at least one surfactant.
27 . The adjuvant composition of claim 26 wherein the surfactant comprises dipalmitoyl phosphatidylcholine (DPPC).
28 . A method for inducing or enhancing immunogenicity of an antigen in a mammal, comprising administering to said mammal a vaccine composition comprising the antigen and a vaccine adjuvant composition comprising an effective immunopotentiatory amount of the compound of claim 1 .
29 . The method of claim 28 wherein said vaccine composition is administered orally, topically, epicutaneously, intramuscularly, intradermally, subcutaneously, intranasally, intravaginally, sublingually, or via inhalation.
30 . A method for treating or preventing a disease in a mammal comprising administering to said mammal a vaccine composition comprising an antigen and an effective immunopotentiatory amount of the compound of claim 1 .
31 . The method of claim 30 wherein the mammal is a human being.
32 . The method of claim 30 wherein the disease is cancer, an autoimmune disease, an allergy, or an infectious disease.
33 . The method of claim 32 wherein the infectious disease is a bacterial or viral infection.
34 . The method of claim 30 wherein the effective amount ranges from about 0.0001 to about 1.0 mg/kg of body weight.
35 . The method of claim 34 wherein the effective amount ranges from about 0.001 to about 0.1 mg/kg of body weight.
36 . The method of claim 30 wherein the compound of claim 1 is administered once weekly to once monthly for a period of up to about 6 months.
37 . The method of claim 36 wherein the effective is administered once monthly for a period of about 2-3 months.
38 . A method for preparing an adjuvant or immunoeffector, said method comprising:
contacting a first compound with the formula: wherein R 2 and R 8 are independently selected from the group consisting of hydrogen, a substituted C 1-20 alkyl group, an unsubstituted C 1-20 alkyl group, and a group having the formula —(CH 2 ) m CH(OH)(CH 2 ) p OR 5 wherein m and p are independently 1 or 2, and R 5 is a substituted C 2-20 acyl group, an unsubstituted C 2-20 acyl group, or a group having the formula: wherein j is an integer from 1 to 5, and R 6 and R 7 are independently selected from the group consisting of hydrogen, a substituted C 1-20 alkyl group, and an unsubstituted C 1-20 alkyl group, with a second compound selected from the group comprising of: MX n , wherein M is selected from the group consisting of Al 3+ , As 3+ , B 3+ , Fe 2+ , Fe 3+ , Ga 3+ , Mg 2+ , Sb 3+ , Sb 5+ , Sn 2+ , Sn 4+ , Ti 2+ , Ti 3+ , Ti 4+ , and Zn 2+ , wherein n is an integer from 2 to 5, MgX 2 -OEt 2 , BX 3 .SMe 2 , Et 2 AlCl, EtAlCl 2 , monoalkyl boronhalides, dialkyl boronhalides, and monoaryl boronhalides, diaryl boronhalides, wherein X is selected from the group consisting of: Cl, I, F, and Br, under conditions sufficient to form a third compound or a pharmacologically acceptable salt thereof with the formula of:
39 . The method of claim 38 , wherein said first compound is:
40 . The method of claim 38 , wherein R 2 is methyl.
41 . The method of claim 38 , wherein R 2 is hydrogen.
42 . The method of claim 38 , wherein the second compound is selected from the group consisting of: AlCl 3 , AlI 3 , AlF 3 , AlBr 3 , Et 2 AlCl, EtAlCl 2 , AsCl 3 , AsI 3 , AsF 3 , AsBr 3 , BCl 3 , BBr 3 , BI 3 , BF 3 , BCl 3 .SMe 2 , BI 3 .SMe 2 , BF 3 .SMe 2 , BBr 3 .SMe 2 , FeCl 3 , FeBr 3 , FeI 3 , FeF 3 , FeCl 2 , FeBr 2 , FeI 2 , FeF 2 , GaCl 3 , GaI 3 , GaF 3 , GaBr 3 , MgCl 2 , MgI 2 , MgF 2 , MgBr 2 , MgCl 2 —OEt 2 , MgI 2 —OEt 2 MgF 2 —OEt 2 MgBr 2 —OEt 2 , SbCl 3 , SbI 3 , SbF 3 , SbBr 3 , SbCl 5 , SbI 5 , SbF 5 , SbBr 5 , SnCl 2 , SnI 2 , SnF 2 , SnBr 2 , SnCl 4 , SnI 4 , SnF 4 , SnBr 4 , TiBr 4 , TiCl 2 , TiCl 3 , TiCl 4 , TiF 3 , TiF 4 , TiI 4 , ZnCl 2 , ZnI 2 , ZnF 2 , and ZnBr 2 .
43 . The method of claim 38 wherein R 2 is (CH 2 ) m CH(OH)(CH 2 ) m OR 5 , wherein m is 1, and R 5 is a substituted C 2-20 acyl group, or an unsubstituted C 2-20 acyl group.
44 . The method of claim 43 , wherein (CH 2 ) m CH(OH)(CH 2 ) m OR 5 is a 1-O-acyl-sn-glyceryl group.
45 . The method of claim 44 , wherein the acyl group is a member selected from the group consisting of acetyl, octanoyl, and tetradecanoyl groups.
46 . The method of claim 38 , wherein R 2 is a group represented by the formula
wherein j is 1; R 6 is a substituted C 1-20 alkyl group, or an unsubstituted C 1-20 alkyl group and R 7 is a substituted C 1-20 alkyl group, or an unsubstituted C 1-20 alkyl group.
47 . The method of claim 46 wherein R 7 is a substituted C 11 alkyl group, or an unsubstituted C 11 alkyl group.Join the waitlist — get patent alerts
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