US 2012/0258928 A1Published application

Nucleoside cyclicphosphates

AssigneeGilead Pharmasset LLC

InventorsJINFA DU, DHANAPALAN NAGARATHNAM, GANAPATI REDDY PAMULAPATI, BRUCE S. ROSS, MICHAEL JOSEPH SOFIA

Life of this patent

Estimating the term…

Abstract

Cyclic phosphate of nucleoside derivatives for the treatment of viral infections in mammals, which is a compound, its stereoisomers, salts (acid or basic addition salts), hydrates, solvates, or crystalline forms thereof, represented by the following structure:

Claims10

Dependent claims

A compound, its stereoisomers, salts (acid or basic addition salts), hydrates, solvates, deuterated analogues, or crystalline forms thereof represented by formula I:

wherein
R1 is hydrogen, n-alkyl, branched alkyl, cycloalkyl, alkaryl, or aryl, which includes, but is not limited to, phenyl or naphthyl, where phenyl or naphthyl are optionally substituted with at least one of H, F, Cl, Br, I, OH, OR′, SH, SR′, NH2, NHR′, NR′2, NHR′2+, NR′3+, lower alkyl, halogenated (F, Cl, Br, I) lower alkyl, halogenated (F, Cl, Br, I) lower alkenyl of C2-C6, lower alkynyl of C2-C6, such as C≡CH, halogenated (F, Cl, Br, I) lower alkynyl of C2-C6, lower alkoxy of C1-C6, halogenated (F, Cl, Br, I) lower alkoxy of C1-C6, CO2H, CO2R′, CONH2, CONHR′, CONR′2, CH═CHCO2H, or CH═CHCO2R′;
R2 is H, an optionally substituted alkyl (including lower alkyl), cyano (CN), CH3, vinyl, O-alkyl, O-(lower alkyl), including OCH3, OCH2CH3, hydroxyl alkyl, i.e., —(CH2)oOH, wherein o is 1-10, hydroxyl lower alkyl, i.e., —(CH2)pOH, where p is 1-6, including hydroxyl methyl (CH2OH), fluoromethyl (CH2F), azido (N3), CH2CN, CH2N3, CH2NH2, CH2NHCH3, CH2N(CH3)2, ethynyl alkyne (optionally substituted), or halogen, including F, Cl, Br, or I;
R3 is H, CH3, CH2F, CHF2, CF3, F, or CN;
X is H, OH, F, OMe, halogen, NH2, or N3;
Base is a naturally occurring or modified purine or pyrimidine base represented by the following structures:
wherein
Z is N or CR9;
R4, R5, R6, R7, and R8 are independently H, F, CI, Br, I, OH, OR′, SH, SR′, NH2, NHR′, NR′2, NHR′2+, NR′3+, heterocycle, lower alkyl, halogenated (F, Cl, Br, I) lower alkyl, lower alkenyl of C2-C6, halogenated (F, Cl, Br, I) lower alkenyl of C2-C6, lower alkynyl of C2-C6 such as C≡CH, halogenated (F, Cl, Br, I) lower alkynyl of C2-C6, lower alkoxy of C1-C6, halogenated (F, Cl, Br, I) lower alkoxy of C1-C6, CO2H, CO2R′, CONH2, CONHR′, CONR′2, CH═CHCO2H, or CH═CHCO2R′;
R9 is an H, halogen (including F, Cl, Br, I), OH, OR′, SH, SR′, NH2, NHR′, NR′2, NO2 lower alkyl, halogenated (F, Cl, Br, I) lower alkyl, lower alkenyl of C2-C6, halogenated (F, Cl, Br, I) lower alkenyl of C2-C6, lower alkynyl of C2-C6, halogenated (F, Cl, Br, I) lower alkynyl of C2-C6, lower alkoxy of C1-C6, halogenated (F, Cl, Br, I) lower alkoxy of C1-C6, CO2H, CO2R′, CONH2, CONHR′, CONR′2, CH═CHCO2H, or CH═CHCO2R′;
wherein R′ is an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkynyl, an optionally substituted alkenyl, or an optionally substituted acyl, an optionally substituted alkoxyalkyl, where for the instance of NR′2 or NHR′2+ each R′ comprise at least one C atom that is independent of one another or are joined to form a heterocycle comprising at least two carbon atoms, and where for the instance of NR′3+ each R′ comprises at least one C atom which are independent of one another or each R′ comprises at least one C atom in which at least two R′ are joined to form a heterocycle comprising at least two carbon atoms.

8 more elements

A compound its stereoisomer, salt, hydrate, solvate, or crystalline form thereof selected from among

1-((2S,4aR,6R,7R,7aR)-7-Fluoro-2-methoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-1H-pyrimidine-2,4-dione;
1-((2R,4aR,6R,7R,7aR)-7-Fluoro-2-methoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-1H-pyrimidine-2,4-dione;
1-((2S,4aR,6R,7R,7aR)-2-Benzyloxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-1H-pyrimidine-2,4-dione;
1-((2R,4aR,6R,7R,7aR)-2-Benzyloxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-1H-pyrimidine-2,4-dione;
6-Azetidin-1-yl-9-((4aR,6R,7R,7aR)-7-fluoro-2-methoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
2-Amino-9-((4aR,6R,7R,7aR)-7-fluoro-2-methoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-6-ol;
4-Amino-1-((2R,4aR,6R,7R,7aR)-7-fluoro-2-methoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-1H-pyrimidin-2-one;
N6-Cyclobutyl-9-((4aR,6R,7R,7aR)-7-fluoro-2-methoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purine-2,6-diamine;
6-Ethoxy-9((4aR,6R,7R,7aR)-7-fluoro-2-methoxy-7-methyl-2-oxo-tetrahydro-2,5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
6-Ethoxy-9-((2S,4aR,6R,7R,7aR)-7-fluoro-2-isopropoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
6-Ethoxy-9-((2R,4aR,6R,7R,7aR)-7-fluoro-2-isopropoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
9-((4aR,6R,7R,7aR)-7-Fluoro-2-methoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-N6-propyl-9H-purine-2,6-diamine;
9-((4aR,6R,7R,7aR)-2-Ethoxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-N6-propyl-9H-purine-2,6-diamine;
9-((4aR,6R,7R,7aR)-7-Fluoro-7-methyl-2-oxo-2-propoxy-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-N6-propyl-9H-purine-2,6-diamine;
9-((4aR,6R,7R,7aR)-7-Fluoro-2-isopropoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-N6-propyl-9H-purine-2,6-diamine;
9-((4aR,6R,7R,7aR)-2-Butoxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-N6-propyl-9H-purine-2,6-diamine;
9-((4aR,6R,7R,7aR)-7-Fluoro-7-methyl-2-oxo-2-phenoxy-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-N6-propyl-9H-purine-2,6-diamine;
N6-Cyclopentyl-9-((4aR,6R,7R,7aR)-7-fluoro-2-methoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purine-2,6-diamine;
6-Azetidin-1-yl-9-((4aR,6R,7R,7aR)-2-ethoxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
6-Azetidin-1-yl-9-((4aR,6R,7R,7aR)-7-fluoro-7-methyl-2-oxo-2-propoxy-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
6-Azetidin-1-yl-9-((4aR,6R,7R,7aR)-7-fluoro-7-methyl-2-oxo-2-propoxy-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
6-Azetidin-1-yl-9-((4aR,6R,7R,7aR)-7-fluoro-2-isopropoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
6-Azetidin-1-yl-9-((4aR,6R,7R,7aR)-2-butoxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
6-Azetidin-1-yl-9-((4aR,6R,7R,7aR)-2-cyclobutoxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
6-Azetidin-1-yl-9-((4aR,6R,7R,7aR)-2-cyclopentyloxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
6-Azetidin-1-yl-9-((4aR,6R,7R,7aR)-2-cyclopentyloxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
6-Azetidin-1-yl-9-((4aR,6R,7R,7aR)-2-cyclohexyloxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
6-Azetidin-1-yl-9-((4aR,6R,7R,7aR)-2-cyclohexyloxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
6-Azetidin-1-yl-9-((4aR,6R,7R,7aR)-2-cyclopropylmethoxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
6-Azetidin-1-yl-9-((4aR,6R,7R,7aR)-2-cyclopropylmethoxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
6-Azetidin-1-yl-9-((4aR,6R,7R,7aR)-7-fluoro-7-methyl-2-oxo-2-phenoxy-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
2-Amino-9-((2S,4aR,6R,7R,7aR)-7-fluoro-7-methyl-2-oxo-2-propoxy-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-6-ol;
2-Amino-9-((2R,4aR,6R,7R,7aR)-7-fluoro-7-methyl-2-oxo-2-propoxy-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-6-ol;
2-Amino-9-((2R,4aR,6R,7R,7aR)-2-butoxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-6-ol;
2-Amino-9-((4aR,6R,7R,7aR)-2-cyclopropylmethoxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-6-ol;
2-Amino-9-((4aR,6R,7R,7aR)-2-cyclopropylmethoxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-6-ol;
2-Amino-9-((4aR,6R,7R,7aR)-2-cyclopentyloxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-6-ol;
2-Amino-9-((2S,4aR,6R,7R,7aR)-2-cyclohexyloxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-6-ol;
2-Amino-9-((2R,4aR,6R,7R,7aR)-2-cyclohexyloxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-6-ol;
(4aR,6R,7R,7aR)-6-(2-Amino-6-methoxy-purin-9-yl)-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-2-ol;
9-((4aR,6R,7R,7aR)-2-Butoxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-6-methoxy-9H-purin-2-ylamine;
9-((4aR,6R,7R,7aR)-2-Butoxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-6-methoxy-9H-purin-2-ylamine;
9-((4aR,6R,7R,7aR)-7-Fluoro-2-isopropoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-6-methoxy-9H-purin-2-ylamine;
9-((2R,4aR,6R,7R,7aR)-7-Fluoro-2-isopropoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-6-methoxy-9H-purin-2-ylamine;
9-((2R,4aR,6R,7R,7aR)-2-Benzyloxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-6-methoxy-9H-purin-2-ylamine;
(4aR,6R,7R,7aR)-6-(2-Amino-6-ethoxy-purin-9-yl)-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-2-ol;
6-Ethoxy-9-((4aR,6R,7R,7aR)-7-fluoro-2-methoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
6-Ethoxy-9-((4aR,6R,7R,7aR)-7-fluoro-7-methyl-2-oxo-2-propoxy-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
6-Ethoxy-9-((2S,4aR,6R,7R,7aR)-7-fluoro-7-methyl-2-oxo-2-propoxy-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
9-((4aR,6R,7R,7aR)-2-Benzyloxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2%5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-6-ethoxy-9H-purin-2-ylamine;
6-Ethoxy-9-((4aR,6R,7R,7aR)-7-fluoro-7-methyl-2-oxo-2-phenoxy-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
9-((4aR,6R,7R,7aR)-7-Fluoro-2-methoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-6-propoxy-9H-purin-2-ylamine;
9-((2S,4aR,6R,7R,7aR)-2-Ethoxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-6-propoxy-9H-purin-2-ylamine;
9-((2R,4aR,6R,7R,7aR)-7-Fluoro-7-methyl-2-oxo-2-propoxy-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-6-propoxy-9H-purin-2-ylamine;
9-((2S,4aR,6R,7R,7aR)-7-Fluoro-7-methyl-2-oxo-2-propoxy-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-6-propoxy-9H-purin-2-ylamine;
9-((2R,4aR,6R,7R,7aR)-7-Fluoro-2-isopropoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-6-propoxy-9H-purin-2-ylamine;
9-((2S,4aR,6R,7R,7aR)-7-Fluoro-2-isopropoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-6-propoxy-9H-purin-2-ylamine;
9-((2S,4aR,6R,7R,7aR)-2-Butoxy-7-fluoro-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-6-propoxy-9H-purin-2-ylamine;
9-((4aR,6R,7R,7aR)-7-Fluoro-7-methyl-2-oxo-2-phenoxy-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-6-propoxy-9H-purin-2-ylamine;
6-Benzyloxy-9-((4aR,6R,7R,7aR)-7-fluoro-2-methoxy-7-methyl-2-oxo-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine;
and
6-Benzyloxy-9-((2S,4aR,6R,7R,7aR)-7-fluoro-7-methyl-2-oxo-2-propoxy-tetrahydro-2λ5-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl)-9H-purin-2-ylamine.

59 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/439,991Filed 5 Apr 2012
Priority: 11 Jun 2008
Published: 11 Oct 2012
Term ends: Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07D 473/18
With oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6: one oxygen and one nitrogen atom, e.g. guanine
A61P 31/12
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antivirals
A61P 31/14
Antivirals: for RNA viruses
C07H 19/10
Pyrimidine radicals: with the saccharide radical esterified by phosphoric or polyphosphoric acids

Family

Application61/060,683Us provisional application · filed 11 Jun 2008
Application61/140,369Us provisional application · filed 23 Dec 2008
Application61/140,317Us provisional application · filed 23 Dec 2008
Application12/479,075Continuation · filed 5 Jun 2009
Application13/439,991Continuation
US 2010/0081628 A1Published application
US 8,173,621 B2Related patent
US 8,759,510 B2Related patent
US 2012/0258928 A1This patent

From the US filing history. Foreign family members aren’t listed.

Timeline

Citations

Open elsewhere

patentgrep

Loading patent…

Abstract

A compound, its stereoisomers, salts (acid or basic addition salts), hydrates, solvates, deuterated analogues, or crystalline forms thereof represented by formula I:

wherein
R1 is hydrogen, n-alkyl, branched alkyl, cycloalkyl, alkaryl, or aryl, which includes, but is not limited to, phenyl or naphthyl, where phenyl or naphthyl are optionally substituted with at least one of H, F, Cl, Br, I, OH, OR′, SH, SR′, NH2, NHR′, NR′2, NHR′2+, NR′3+, lower alkyl, halogenated (F, Cl, Br, I) lower alkyl, halogenated (F, Cl, Br, I) lower alkenyl of C2-C6, lower alkynyl of C2-C6, such as C≡CH, halogenated (F, Cl, Br, I) lower alkynyl of C2-C6, lower alkoxy of C1-C6, halogenated (F, Cl, Br, I) lower alkoxy of C1-C6, CO2H, CO2R′, CONH2, CONHR′, CONR′2, CH═CHCO2H, or CH═CHCO2R′;
R2 is H, an optionally substituted alkyl (including lower alkyl), cyano (CN), CH3, vinyl, O-alkyl, O-(lower alkyl), including OCH3, OCH2CH3, hydroxyl alkyl, i.e., —(CH2)oOH, wherein o is 1-10, hydroxyl lower alkyl, i.e., —(CH2)pOH, where p is 1-6, including hydroxyl methyl (CH2OH), fluoromethyl (CH2F), azido (N3), CH2CN, CH2N3, CH2NH2, CH2NHCH3, CH2N(CH3)2, ethynyl alkyne (optionally substituted), or halogen, including F, Cl, Br, or I;
R3 is H, CH3, CH2F, CHF2, CF3, F, or CN;
X is H, OH, F, OMe, halogen, NH2, or N3;
Base is a naturally occurring or modified purine or pyrimidine base represented by the following structures:
wherein
Z is N or CR9;
R4, R5, R6, R7, and R8 are independently H, F, CI, Br, I, OH, OR′, SH, SR′, NH2, NHR′, NR′2, NHR′2+, NR′3+, heterocycle, lower alkyl, halogenated (F, Cl, Br, I) lower alkyl, lower alkenyl of C2-C6, halogenated (F, Cl, Br, I) lower alkenyl of C2-C6, lower alkynyl of C2-C6 such as C≡CH, halogenated (F, Cl, Br, I) lower alkynyl of C2-C6, lower alkoxy of C1-C6, halogenated (F, Cl, Br, I) lower alkoxy of C1-C6, CO2H, CO2R′, CONH2, CONHR′, CONR′2, CH═CHCO2H, or CH═CHCO2R′;
R9 is an H, halogen (including F, Cl, Br, I), OH, OR′, SH, SR′, NH2, NHR′, NR′2, NO2 lower alkyl, halogenated (F, Cl, Br, I) lower alkyl, lower alkenyl of C2-C6, halogenated (F, Cl, Br, I) lower alkenyl of C2-C6, lower alkynyl of C2-C6, halogenated (F, Cl, Br, I) lower alkynyl of C2-C6, lower alkoxy of C1-C6, halogenated (F, Cl, Br, I) lower alkoxy of C1-C6, CO2H, CO2R′, CONH2, CONHR′, CONR′2, CH═CHCO2H, or CH═CHCO2R′;
wherein R′ is an optionally substituted alkyl, an optionally substituted cycloalkyl, an optionally substituted alkynyl, an optionally substituted alkenyl, or an optionally substituted acyl, an optionally substituted alkoxyalkyl, where for the instance of NR′2 or NHR′2+ each R′ comprise at least one C atom that is independent of one another or are joined to form a heterocycle comprising at least two carbon atoms, and where for the instance of NR′3+ each R′ comprises at least one C atom which are independent of one another or each R′ comprises at least one C atom in which at least two R′ are joined to form a heterocycle comprising at least two carbon atoms.

8 more elements

Facts

Application

13/439,991Filed 5 Apr 2012

Priority

11 Jun 2008

Published

11 Oct 2012

Term ends

Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07D 473/18
With oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6: one oxygen and one nitrogen atom, e.g. guanine
A61P 31/12
Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics: antivirals
A61P 31/14
Antivirals: for RNA viruses
C07H 19/10
Pyrimidine radicals: with the saccharide radical esterified by phosphoric or polyphosphoric acids

Family

Application61/060,683Us provisional application · filed 11 Jun 2008

Application61/140,369Us provisional application · filed 23 Dec 2008

Application61/140,317Us provisional application · filed 23 Dec 2008

Application12/479,075Continuation · filed 5 Jun 2009

Application13/439,991Continuation

US 2010/0081628 A1Published application

US 8,173,621 B2Related patent

US 8,759,510 B2Related patent

US 2012/0258928 A1This patent

From the US filing history. Foreign family members aren’t listed.