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US 6,552,183 B1Granted
Moncyclic L-nucleosides analogs
AssigneeICN Pharmaceuticals, Inc.
InventorsKandasamy Ramasamy, Robert Tam, Devron Averett
Life of this patent
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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.
Claims2
A compound having a structure according to Formula III:
- wherein:
- X is independently O, S, CH2 and NR, where R is COCH3;
- R′ and R″ are independently selected from the group consisting of H, CN, C(═O)NH2, NH2, C(═S)NH2, C(═NH)NH2.HCl, C(═NOH)NH2, C(═NH)OMe, a halogen, lower alkyl and a lower alkyl aryl;
- R1 and R4 are independently selected from the group consisting of H, CN, N3, CH2OH, lower alkyl and a lower alkyl amino;
- and
- 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 a lower alkyl amino, with the proviso that when R2═R3═H, then each of R7 and R8 is a hydrogen or taken together are a π-bond;
- and
- where in compounds of Formula III, R′ is carboxamide or CN and R″ is hydrogen or a halogen;
- R1═R4═R5═R7═R8 H and R2═R3═OH, and X is oxygen.
6 more elements
A compound having a structure according to Formula IV:
- wherein:
- A is independently selected from the group consisting of N and C;
- B, T, E and J are independently selected from the group consisting of CH, CO, N, S, NR1′, CCONH2, CCH3, and C-Rb′;
- Ra′ is independently H, lower alkyl, a lower alkylamine, COCH3, lower alkyl alkenyl, lower alkyl vinyl or a lower alkyl aryl;
- Rb′ is independently H, OH, a halogen, CN, N3, NH2, C(═O)NH2, C(═S)NH2, C(═NH)NH2.HCl, C(═NOH)NH2, C(═NH)OMe, lower alkyl, a lower alkylamine, lower alkyl alkenyl, lower alkyl vinyl, or a lower alkyl aryl;
- X is independently O or NR;
- where R is COCH3;
- R1 and R4 are independently selected from the group consisting of H, CN, N3, CH2OH, lower alkyl and a lower alkyl amino;
- and
- R2, R3, R5, R6, R7 and R8 are independently selected from the group consisting of H, OH, CN, N3, a halogen, NH2, CH2OH, OCH3, NHCH3, ONHCH3, SCH3, SPh, alkenyl, allyl, lower alkyl, and a lower alkyl amino, with the proviso that when R2═R3═H, then R7 and R8 are a hydrogen or taken together are a π-bond;
- such that
- when A is carbon;
- B═E═N;
- T is N—Ph, then J is CO, N, S, NRa′, CCONH2, CCH3, and C-Rb′;
- Ra′ is independently H, lower alkyl, a lower alkylamine, COCH3, lower alkyl alkenyl, lower alkyl vinyl or a lower alkyl aryl;
- Rb′ is independently H, OH, a halogen, CN, N3, NH2, C(═O)NH2, C(═S)NH2, C(═NH)NH2.HCl, C(═NOH)NH2, C(═NH)OMe, lower alkyl, a lower alkylamine, lower alkyl alkenyl, lower alkyl vinyl, or a lower alkyl aryl;
- when A═N;
- T is CH;
- B═E═C—CH3, then J is CO, CN, S, NRa′, CCONH2, CCH3, and C-Rb′;
- Ra′ is independently H, lower alkyl, a lower alkylamine, COCH3, lower alkyl alkenyl, lower alkyl vinyl or a lower alkyl aryl;
- R2′ is independently H, OH, a halogen, CN, N3, NH2, C(═O)NH2, C(═S)NH2, C(═NH)NH2.HCl, C(═NOH)NH2, C(═NH)OMe, lower alkyl, a lower alkylamine, lower alkyl alkenyl, lower alkyl vinyl, or a lower alkyl aryl;
- when A is carbon, B═N;
- T═C—CONH2;
- E═CH;
- J=S, then X is O or NR;
- where R is COCH3;
- and
- where in compounds of Formula IV, R1 is H, lower alkyl or allyl;
- R2 is H, OH, a halogen, CN, N3, NH2, C(═O)NH2, C(═S)NH2, C(═NH)NH2.HCl, C(═NOH)NH2 or C(═NH)OMe;
- and when R1═R4═R5═R7═R8═H, then R2═R3═OH and X is oxygen.
27 more elements
Dependencies are inferred from the claim text.