Monocyclic L-nucleosides, analogs and uses thereof
First Claim
Patent Images
1. A compound having a structure according to Formula I, in which the sugar is in an L-configuration:
-
wherein;
A is N;
B, C, E, F are independently selected from the group consisting of CH, N, S, O, NR1′
, CCONH2, and C—
R2;
R1′
is H, lower alkyl, lower alkylamino, COCH3, lower alkyl alkenyl, lower alkyl vinyl or lower alkyl aryl;
R2′
is H, OH, a halogen, CN, N3, NH2, C(═
O)NH2, C(═
S)NH2, C(═
NH)NH2HCl, C(═
NOH)NH2, C(═
NH)OMe, lower alkyl, lower alkylamino, lower alkyl alkenyl, lower alkyl vinyl, or lower alkyl aryl;
D is absent;
X is O, S, or CH2;
R1 and R4 are independently selected from the group consisting of H, CN, N3, CH2OH, lower alkyl, and lower alkylamino;
R2, R3, R5, R6, R7 and R8 are independently selected from the group consisting of H, OH, CN, N3, a halogen, CH2OH, NH2, OCH3, NHCH3, ONHCH3, SCH3, SPh, alkenyl, lower alkyl, and lower alkyl amino; and
with the proviso that at least one of the variables R1, R2, R3, R4, R5, R6, R7 and R8 must be hydrogen;
such that when R2=R3═
H, and X is oxygen, then R7, and R8 are independently CN, N3, a halogen, CH2OH, NH2, OCH3, NHCH3, ONHCH3, SCH3, SPh, alkenyl, lower alkyl, or lower alkyl amino when R1 or R4 is CN, N3, CH2OH, lower alkyl, or lower alkylamino, or R5 is OH, CN, N3, halogen, CH2OH, NH2, OCH3, NHCH3, ONHCH3, SCH3, SPh, alkenyl, lower alkyl, or a lower alkyl amino, then R7=R8=H and R2=R3=OH;
when R2 or R3 are OH, CN, N3, halogen, CH2OH, NH2, OCH3, NHCH3, ONHCH3, SCH3, SPh, alkenyl, lower alkyl, or lower alkyl amino, then R7 and R8 are H or OH;
when R7 or R8 are OH, CN, N3, halogen, CH2OH, NH2, OCH3, NHCH3, ONHCH3, SCH3, SPh, alkenyl, lower alkyl, or lower alkyl amino, then R2 and R3 are H or OH; and
when R7 and R8 are hydroxyl, then R2 and R3 are not OH.
3 Assignments
0 Petitions
Accused Products
Abstract
Novel monocyclic L-Nucleoside compounds have the general formula
Embodiments of these compounds are contemplated to be useful in treating a wide variety of diseases including infections, infestations, neoplasms, and autoimmune diseases. Viewed in terms of mechanism, embodiments of the novel compounds show immunomodulatory activity, and are expected to be useful in modulating the cytokine pattern, including modulation of Th1 and Th2 response.
-
Citations
10 Claims
-
1. A compound having a structure according to Formula I, in which the sugar is in an L-configuration:
-
wherein; A is N;
B, C, E, F are independently selected from the group consisting of CH, N, S, O, NR1′
, CCONH2, and C—
R2;
R1′
is H, lower alkyl, lower alkylamino, COCH3, lower alkyl alkenyl, lower alkyl vinyl or lower alkyl aryl;
R2′
is H, OH, a halogen, CN, N3, NH2, C(═
O)NH2, C(═
S)NH2, C(═
NH)NH2HCl, C(═
NOH)NH2, C(═
NH)OMe, lower alkyl, lower alkylamino, lower alkyl alkenyl, lower alkyl vinyl, or lower alkyl aryl;
D is absent;
X is O, S, or CH2;
R1 and R4 are independently selected from the group consisting of H, CN, N3, CH2OH, lower alkyl, and lower alkylamino;
R2, R3, R5, R6, R7 and R8 are independently selected from the group consisting of H, OH, CN, N3, a halogen, CH2OH, NH2, OCH3, NHCH3, ONHCH3, SCH3, SPh, alkenyl, lower alkyl, and lower alkyl amino; and
with the proviso that at least one of the variables R1, R2, R3, R4, R5, R6, R7 and R8 must be hydrogen;
such thatwhen R2=R3═
H, and X is oxygen, then R7, and R8 are independently CN, N3, a halogen, CH2OH, NH2, OCH3, NHCH3, ONHCH3, SCH3, SPh, alkenyl, lower alkyl, or lower alkyl aminowhen R1 or R4 is CN, N3, CH2OH, lower alkyl, or lower alkylamino, or R5 is OH, CN, N3, halogen, CH2OH, NH2, OCH3, NHCH3, ONHCH3, SCH3, SPh, alkenyl, lower alkyl, or a lower alkyl amino, then R7=R8=H and R2=R3=OH;
when R2 or R3 are OH, CN, N3, halogen, CH2OH, NH2, OCH3, NHCH3, ONHCH3, SCH3, SPh, alkenyl, lower alkyl, or lower alkyl amino, then R7 and R8 are H or OH;
when R7 or R8 are OH, CN, N3, halogen, CH2OH, NH2, OCH3, NHCH3, ONHCH3, SCH3, SPh, alkenyl, lower alkyl, or lower alkyl amino, then R2 and R3 are H or OH; and
when R7 and R8 are hydroxyl, then R2 and R3 are not OH. - View Dependent Claims (2, 3, 4, 5, 6, 7, 8, 9, 10)
providing a compound according to claim 1 or 2; and
administering a dose of the compound to the patient.
-
-
4. The method of claim 3 wherein the condition comprises an infection.
-
5. The method of claim 3 wherein the condition comprises an infestation.
-
6. The method of claim 3 wherein the condition comprises a neoplasm.
-
7. The method of claim 3 wherein the condition comprises an autoimmune disease.
-
8. A method of changing expression of a Th1 cytokine relative to a Th2 cytokine in a peripheral blood mononuclear cell comprising:
-
providing a compound according to claim 1 or 2; and
administering a dose of the compound to the peripheral blood mononuclear cell.
-
-
9. The method of claim 8 wherein administration of the compound to the peripheral blood mononuclear cell is in vivo.
-
10. The method of claim 9 wherein the peripheral blood mononuclear cell is in a system having an inflammation.
Specification
-
- Resources
Litigation Campaign Assessment
Thank you for your request. You will receive a custom alert email when the Litigation Campaign Assessment is available.
×
-
Current AssigneeRibapharm Inc. (Bausch Health Cos., Inc.)
-
Original AssigneeICN Pharmaceuticals, Inc (Bausch Health Cos., Inc.)
-
InventorsTam, Robert, Averett, Devron, Ramasamy, Kandasamy
-
Primary Examiner(s)Wilson, James O.
-
Assistant Examiner(s)Crane, Lawrence E
-
Application NumberUS09/969,355Publication NumberTime in Patent Office519 DaysField of Search514/43, 514/49-50, 536/28.1, 536/28.2, 536/28.3, 536/28.4, 536/28.5, 536/28.53, 536/28.6, 536/28.7, 536/28.8, 544/224, 548/255, 548/252.2, 548/300.1, 548/356.1, 548/400US Class Current514/43CPC Class CodesA61P 31/00 Antiinfectives, i.e. antibi...A61P 33/00 Antiparasitic agentsA61P 35/00 Antineoplastic agentsA61P 37/02 ImmunomodulatorsA61P 37/06 Immunosuppressants, e.g. dr...C07H 19/04 Heterocyclic radicals conta...
