US2004147480A1PendingUtilityA1
Prophylactic and therapeutic treatment of infectious and other diseases with mono-and disaccharide-based compounds
Est. expiryMay 19, 2020(expired)· nominal 20-yr term from priority
Inventors:David H. PersingRichard CraneGary T. ElliottJ. Terry UlrichMichael LacyDavid A. JohnsonJory BaldridgeRong Wang
A61P 37/02A61P 37/08A61P 11/06A61P 17/06A61K 31/7008C07H 13/04C07H 11/00C07H 15/14A61K 31/7024C07H 13/06
54
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Claims
Abstract
Methods and compositions for treating or ameliorating diseases and other conditions, such as infectious diseases, autoimmune diseases and allergies are provided. The methods employ mono- and disaccharide-based compounds for selectively stimulating immune responses in animals and plants.
Claims
exact text as granted — not AI-modifiedWhat is claimed is:
1 . A method for modulating the production of cytokines in a subject in need of such modulation comprising administering to the subject an effective amount of one or more compounds having the formula:
and pharmaceutically acceptable salts thereof, wherein
X is a member selected from the group consisting of —O— and —NH—;
R 1 and R 2 are each members independently selected from the group consisting of (C 2 -C 24 )acyl;
R 3 is a member selected from the group consisting of H and —PO 3 R 11 R 12 , wherein R 11 and R 12 are each members independently selected from the group consisting of —H and (C 1- C 4 )alkyl;
R 4 is a member selected from the group consisting of —H, —CH 3 and —PO 3 R 13 R 14 , wherein R 13 and R 14 are each members independently selected from the group consisting of —H and (C 1 -C 4 )alkyl; and
Y is a radical selected from the group consisting of
wherein the subscripts n, m, p and q are each independently an integer of from 0 to 6;
R 5 is (C 2 -C 24 )acyl;
R 6 and R 7 are members independently selected from the group consisting of H and CH 3 ;
R 8 and R 9 are members independently selected from the group consisting of H, OH, (C 1 -C 4 )alkoxy, —PO 3 H 2 , —OPO 3 H 2 , —SO 3 H, —OSO 3 H, - NR15R16 , —SR 15 , —CN, —NO 2 , —CHO, —CO 2 R 15 , —CONR 15 R 16 , —PO 3 R 15 R 16 , —OPO 3 R 15 R 16 , —SO 3 R 15 and —OSO 3 R 15 and R 16 are each members independently selected from the group consisting of H and (C 1 -C 4 )alkyl;
R 10 is a member selected from the group consisting of H, CH 3 , —PO 3 H 2 , -phosphonooxy(C 2 -C 24 )alkyl, and -carboxy(C 1 -C 24 )alkyl; and
Z is —O or —S—;
with the proviso that when R 3 is —PO 3 R 11 R 12 , R 4 is other than —PO 3 R 13 R 14 , and with the further proviso that when R 3 is —PO 3 H 2 , R 4 is H, R 10 is H, R 1 is n-tetradecanoyl, R 2 is n-octadecanoyl and R 5 is n-hexadecanoyl, then X is other than —O—.
2 . A method in accordance with claim 1 , wherein the compound or compounds are administered in the form of pharmaceutically acceptable salts.
3 . A method in accordance with claim 1 , comprising administering a prodrug or prodrugs of the compound or compounds.
4 . A method in accordance with claim 1 , wherein the compound or compounds are administered in the form of a composition further comprising one or more pharmaceutically acceptable carriers.
5 . A method in accordance with claim 1 , wherein the compound or compounds are administered in the form of an aqueous composition comprising water and one or more surfactants.
6 . A method in accordance with claim 5 , wherein said one or more surfactants are selected from the group consisting of dimyristoyl phosphatidyl glycerol (DPMG), dipalmitoyl phosphatidyl glycerol (DPPG), distearoyl phosphatidyl glycerol (DSPG), dimyristoyl phosphatidylcholine (DPMC), dipalmitoyl phosphatidylcholine (DPPC), distearoyl phosphatidylcholine (DSPC); dimyristoyl phosphatidic acid (DPMA), dipalmitoyl phosphatidic acid (DPPA), distearoyl phosphatidic acid (DSPA); dimyristoyl phosphatidyl ethanolamine (DPME), dipalmitoyl phosphatidyl ethanolamine (DPPE) and distearoyl phosphatidyl ethanolamine (DSPE).
7 . A method in accordance with claim 5 , wherein the molar ratio of said compound or compounds to surfactant is from about 10:1 to about 1:10.
8 . A method in accordance with claim 1 , wherein at least one of said R 1 , R 2 and R 5 are selected from the group consisting of (C 2 -C 6 )acyl.
9 . A method in accordance with claim 1 , wherein at least one of said R 1 , R 2 and R 5 is selected from the group consisting of (C 2 -C 6 )acyl and the total number of carbon atoms in R 1 , R 2 and R 5 is from about 6 to about 22.
10 . A method in accordance with claim 1 , wherein at least one of said R 1 , R 2 and R 5 are selected from the group consisting of (C 2 -C 6 )acyl and the total number of carbon atoms in R 1 , R 2 and R 5 is from about 12 to about 18.
11 . A method in accordance with claim 1 , wherein X and Z are both —O—.
12 . A method in accordance with claim 1 , wherein R 1 , R 2 and R 5 are each independently selected from the group consisting of (C 12 -C 24 )acyl with the proviso that the total number of carbon atoms in R 1 , R 2 and R 5 is from about 44 to about 60.
13 . A method in accordance with claim 12 , wherein said total number of carbon atoms is from about 46 to about 52.
14 . A method in accordance with claim 12 , wherein X and Z are both —O—.
15 . A method in accordance with claim 1 , wherein at least one of said R 1 , R 2 and R 5 are selected from the group consisting of (C 6 -C 12 ) acyl.
16 . A method in accordance with claim. 1, wherein at least one of said R 1 , R 2 and R are selected from the group consisting of (C 6 -C 12 ) acyl and the total number of carbon atoms in R 1 , R 2 and R 5 is from about 18 to about 36.
17 . A method in accordance with claim 15 , wherein at least one of said R 1 , R 2 and R 5 is a C 6 acyl group and at least one of said R 1 , R 2 and R 5 is a C 10 acyl group.
18 . A method in accordance with claim 1 , wherein said compound or compounds is administered to said subject by a route selected from the group consisting of parenteral, oral, intravenous, infusion, intranasal, inhalation, transdermal and transmucosal.
19 . A method in accordance with claim 1 , wherein said compound or compounds is administered intranasally.
20 . A method in accordance with claim 1 , wherein the production of cytokines in the subject is enhanced.
21 . A method in accordance with claim 1 , wherein the production of cytokines is inhibited.
22 . A method in accordance with claim 1 , wherein Y is
and R 8 is CO 2 H.
23 . A method in accordance with claim 22 , wherein X is O, Y is O, n, m, p and q are 0; R 3 is phosphono; and R 4 , R 6 , R 7 and R 9 are hydrogen.
24 . A method in accordance with claim 22 , wherein R 1 , R 2 and R 5 are all C 6 acyl.
25 . A method in accordance with claim 22 , wherein R 1 , R 2 and R 1 are all C 7 acyl.
26 . A method in accordance with claim 22 , wherein R 1 , R 2 and R 5 are all C 8 acyl.
27 . A method in accordance with claim 22 , wherein R 1 , R 2 and R 5 are all C 9 acyl.
28 . A method in accordance with claim 22 , wherein R 1 , R 2 and R 5 are all C 10 acyl.
29 . A method in accordance with claim 22 , wherein R 1 , R 2 and R 5 are all C 11 acyl.
30 . A method in accordance with claim 22 , wherein R 1 , R 2 and R 5 are all C 12 acyl.
31 . A method in accordance with claim 22 , wherein R 1 , R 2 and R 5 are all C 14 acyl.
32 . A method in accordance with claim 22 , wherein at least one of R 1 , R 2 and R 5 is C 6 acyl and at least one other of R 1 , R 2 and R 5 is C 10 acyl.
33 . A method in accordance with claim 22 , wherein R 1 is C 10 acyl and R 2 and R 5 are both C 6 acyl.
34 . A method in accordance with claim 22 , wherein R 5 is C 10 acyl and R 1 and R 2 are both C 6 acyl.
35 . A method in accordance with claim 22 , wherein R 1 is C 6 acyl and R 2 and R 5 are both C 10 acyl.Cited by (0)
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