US 2002/0120139 A1Published application

Pyrimidinone compounds and pharmaceutical compositions containing them

OwnerDeirdre Mary Bernadette Hickey, Robert John Ife +4inventors

InventorsDeirdre Mary Bernadette Hickey, Robert John Ife, Colin Andrew Leach, Ivan Leo Pinto, Roderick Alan Porter, Stephen Allan Smith

Life of this patent

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Abstract

A group of novel pyrimidone compounds are inhibitors of the enzyme LDL PLA2 and therefore of use in treating atherosclerosis.

Claims19

Dependent claims

A compounds of formula (I):

608
in which:
Z is a bond and R1 is halogen;
or
Z is CR3R4, where R3 and R4 are each hydrogen or C(1-4)alkyl, or R3 and R4 together with the intervening carbon atom form a C(3-6)cycloalkyl ring;
and
R1 is an aryl or heteroaryl group, optionally substituted by 1, 2, 3 or 4 substituents selected from C(1-18)alkyl, C(1-18)alkoxy, C(1-18)alkylthio, arylC(1-18)alkoxy, oxo, hydroxy, halogen, CN, COR5, COOR5, CONR5R6, NR5COR6, SO2NR5R6, NR5SO2R6, NR5R6, mono to perfluoro-C(1-4)alkyl and mono to perfluoro-C(1-4)alkoxy;
X is O or S;
Y is a group of formula -A1-A2-A3- in which A1 and A3 each represent a bond or a straight chain or branched C(1-10)alkylene group and A2 represents a bond or O, S, SO, SO2, CO, C═CH2, C═CH, C≡C, CONH, NHCO, or CR5R6, providing that when A2 is O, S, SO, SO2 or CONH, A3 contains at least two carbon atoms linking the A2 group and the CH2 group in formula (I);
R2 is an aryl or heteroaryl group, optionally substituted by 1, 2, 3 or 4 substituents selected from the substituents hereinbefore defined for R1, as well as aryl and arylC(1-4)alkyl;
W is a bond and R7 is hydrogen;
or
W is SO2 or a bond;
and
R7 is R1 or a hydrocarbyl group which hydrocarbyl group may be optionally interupted within the carbon chain by a group selected from O, COO, OCO, CO, CONR8, NR8CO, NR8CONR9, NR8COO, OCONR8, and NR8, and which hydrocarbyl group may also be optionally substituted by 1 or 2 substituents selected from mono to perfluoro-C(1-4)alkyl, OR8, COOR8, CONR8R9, NR8COR9, NR8CONR9R10, NR8COOR9, OCONR8R9, NR11R12 and R1;
R5 and R6 are independently hydrogen or C(1-20)alkyl, for instance C(1-4)alkyl (e.g. methyl or ethyl);
R8, R9 and R10 are independently selected from hydrogen, C(1-20)alkyl (for instance C(1-15)alkyl), (which may optionally be fluorinated, including up to perfluorinated on the terminal 1 to 3 carbon atoms), C(1-20)alkenyl (preferably C(12-18)alkenyl), aryl, arylC(1-10)alkyl, C(1-10)alkoxyC(1-10)alkyl, or aryloxyC(1-10)alkyl and in which an aryl group may have one or two substituents selected from halogen, C(1-20)alkyl, C(1-20)alkoxy, aryloxy and COOC(1-20)alkyl;
and
R11 and R12 are independently selected from one of the values hereinbefore defined for R8 and R9 or R11 and R12 together with the nitrogen atom to which they are attached form a 5- to 7 membered ring optionally containing one or two further heteroatoms selected from oxygen, nitrogen and sulphur, and optionally substituted by one or two substituents selected from hydroxy, oxo, C(1-4)alkyl, phenyl, or benzyl.

16 more elements

A compound selected from:

2-(8-Phenyloct-1-yl)thio-5-((1-benzyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
2-(8-(4-Fluorophenyl)oct-1-yl)thio-5-((1-benzyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;hyl)pyrimidin-4-one;
2-(8-(4-Chlorophenyl)-8-oxooct-1-yl)thio-5-((1-benzyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
2-(8-(4-Fluorophenyl)-8-oxooct-1-yl)thio-5-((1-benzyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
2-(9-Phenylnon-1-yl)thio-5-((1-benzyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
2-(6-Phenylhex-1-yl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
2-(7-Phenylhept-1-yl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one
2-(8-Phenyloct-1-yl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
2-(9-Phenylnon-1-yl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
2-(6-Benzyloxyhex-1-yl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
2-(8-(4-Chlorophenyl)-8-oxooct-1-yl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
2-(8-Phenyloct-1-yl)thio-5-((1-butyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
2-(8-Phenyloct-1-yl)thio-5-((2,3-dimethylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(6-Benzyloxyhex-1-yl)thio-5-((2,3-dimethylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(8-Phenyloct-1-yl)thio-5-((2,4-dimethylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(5-Phenylpent-1-yl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(N-(6-(4-Fluorophenyl)hexyl)carboxamidomethyl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(6-Benzyloxyhex-1-yl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(8-Phenyloct-1-yl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(7-Phenylhept-1-yl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(6-Phenylhex-1-yl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(9-Phenylnon-1-yl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(6-(4-Chlorobenzyloxy)hex-1-yl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(6-(4-Fluorobenzyloxy)hex-1-yl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(8-(4-Methoxyphenyl)-8-oxooct-1-yl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(8-(Methoxyphenyl)oct-1-yl)thio-5-((2-methyl pyrid-5-yl)methyl)pyrimidin-4-one;
2-(8-(4-Fluorophenyl)oct-1-yl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(8-(4-Fluorophenyl)-8-oxooct-1-yl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(8-(4-Chlorophenyl)oct-1-y)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(8-(4-Chlorophenyl)-8-oxooct-1-yl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(8-Phenyl-8-oxooct-1-yl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(8-(4-Chlorophenyl)-8-hydroxyoct-1-yl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(8-(4-Methylphenyl)-8-oxooct-1-yl)thio-5-(((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(4-Phenylbut-1-yl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(8-Phenyloct-1-yl)thio-5-((1-oxo-2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(8-Phenyloct-1-yl)thio-5-((2-methoxypyrid-4-yl)methyl)pyrimidin-4-one,
2-(8-(4-Chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrazin-2-ylmethyl)pyrimidin-4-one;
2-(8-Phenyloct-1-yl)thio-5-(pyrid-2-ylmethyl)pyrimidin-4-one;
2-(8-(4-Chlorophenyl)-8-oxooct-1-yl)thio-5-(thiazol-2-ylmethyl)pyrimidin-4-one;
2-(6-Phenylhex-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(7-Phenylhept-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(8-Phenyloct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(9-Phenylnon-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(6-Benzyloxyhex-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(8-(4-Chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(8-(4-Fluorophenyl)non-8-en-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(6-(4-Chlorobenzoylamino)hex-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(8-(4-Bromophenyl)-8-oxooct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(7-(4-Chlorophenoxy)hept-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(7-Phenoxyhept-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(7-Phenylthiohept-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(7-(4-Chlorophenylthio)hept-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(6-(3-Chlorophenyl)hex-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(7-Phenylsulfinylhept-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(7-(4-Chlorophenylsulfinyl)hept-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(7-Phenylsulfonylhept-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(7-(4-Chlorophenylsulfonyl)hept-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(8-(3-Chlorophenyl)oct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(8-(3,4-Dichlorophenyl)oct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(8-(2-Thienyl)-8-oxooct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(8-(2-Furyl)-8-oxooct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(8-(2-Pyridyl)oct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(9-(4-Chlorophenyl)-9-oxonon-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(8-(3,4-Dichlorophenyl)oct-7-yn-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(8-(4-Acetylphenyl)oct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(8-(4-Methylnaphth-1-yl)-8-oxooct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4one;
2-(8-(4-Pyridyl)oct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(8-(4-Chlorophenyl)oct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(4-(3-Phenylprop-1-yloxy)but-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(6-Benzyloxyhex-1-yl)thio-5-(quinolin-3-ylmethyl)pyrimidin-4-one;
2-(8-Phenyloct-1-yl)thio-5-(quinolin-3-ylmethyl)pyrimidin-4-one;
2-(8-Phenyloct-1-yl)thio-5-((4-methoxypyrid-2-yl)methyl)pyrimidin-4-one;
2-(8-Phenyloct-1-yl)thio-5-(2-oxopyrid-4-ylmethyl)pyrimidin-4-one;
2-(8-Phenyloct-1-yl)thio-5-(pyrid-4-ylmethyl)pyrimidin-4-one;
2-(6-Benzyloxyhex-1-yl)thio-5-(pyrid-4-ylmethyl)pyrimidin-4one;
2-(8-(4-Chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
2-(8-Phenyloct-1-yl)thio-5-(fur-2-ylmethyl)pyrimidin-4-one;
2-(6-Benzyloxyhex-1-y;)thio-5-(fur-2-ylmethyl)pyrimidin-4-one;
2-(6-Benzyloxyhex-1-yl)thio-5-(fur-3-ylmethyl)pyrimidin-4-one;
2-(8-Phenyloct-1-yl) thio-5-(fur-3-ylmethyl)pyrimidin-4-one;
2-Benzylthio-5-((1-methyl-2-oxo-pyrid-4yl)methyl)pyrimidin-4one;
2-Benzylthio-5-(fur-2-ylmethyl)pyrimidin-4-one;
2-(3-Chlorobenzyl)thio-5-(fur-2-ylmethyl)pyrimidin-4-one;
2-(4-Chlorobenzyl)thio-5-(fur-2-ylmethyl)pyrimidin-4-one;
2-Benzylthio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-Benzylthio-5-((2-methoxypyrid-4-yl)methyl)pyrimidin-4-one;
2-Benzyl thio-5-(pyrazin-2-ylmethyl)pyrimidin-4-one;
2-Benzylthio-5-(thiazol-2-ylmethyl)pyrimidin-4-one;
2-(4-Chlorobenzyl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-Benzylthio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(3,4-Dichlorobenzyl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-Benzylthio-5-(pyrid-4-ylmethyl)pyrimidin-4-one;
2-(4-Chlorobenzyl)thio-5-(pyrid-4-ylmethyl)pyrimidin-4-one;
2-(3,4-Dichlorobenzyl)thio-5-(pyrid-4-ylmethyl)pyrimidin-4-one;
2-Benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
2-Benzylthio-5-(2-(pyrid-4-yl)ethyl)pyrimidin-4-one,
2-Benzylthio-5-benzylpyrimidin-4-one;
2-(8-Phenyloct-1-yl)oxy-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(8-(4-Chlorophenyl)-8-oxooct-1-yl)oxy-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
2-(4-Phenylbut-1-yl)oxy-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(2-Phenylethyl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
2-(2-Phenylethyl)thio-5-((2-methoxypyrid-4-yl)methyl)pyrimidin-4-one;
2-Benzylthio-5-((1-methylpyrazol-4-yl)methyl)pyrimidin-4-one;
2-(4-Fluorobenzylthio)-5-((pyrimid-5-yl)methyl)pyrimidin-4-one;
2-(3,4-Difluorobenzylthio)-5-((2-methoxypyrimid-5-yl)methyl)pyrimidin-4-one;
2-(4-Fluorobenzylthio)-5-((2-methoxypyrimid-5-yl)methyl)pyrimidin-4-one;
2-(4-Fluorobenzylthio)-5-((2-benzyloxypyrimid-5-yl)methyl)pyrimidin-4-one;
1-(4-Hydroxycyclohexyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-yl-methyl)pyrimidin-4-one;
1-(2-Methoxyethyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)-pyrimidin-4-one;
1-(3-(1-Imidazolyl)prop-1-yl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-yl-methyl)pyrimidin-4-one;
1-(3-(1-Morpholino)prop-1-yl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(2-Oxo-1-pyrrolidino)prop-1-yl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Dimethylaminoprop-1-yl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one.
1-(3-Hydroxyprop-1-yl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Hydroxyprop-1-yl)-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-benzylpyrimidin-4-one;
1-(3-Methoxyprop-1-yl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Phenylprop-1-yl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(5-Hydroxypent-1-yl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Pyrid-2-ylmethyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Pyrid-2-ylmethyl)-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-benzylpyrimidin-4-one;
1-(Pyrid-3-ylmethyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
1-(Pyrid-3-ylmethyl)-2-(8-(4-chlorophenyl)-g-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Pyrid-3-ylmethyl)-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-benzylpyrimidin-4-one;
1-(Pyrid-4-ylmethyl)-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
1-(Pyrid-4-ylmethyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
1-(Pyrid-4-ylmethyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Pyrid-4-ylmethyl)-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-benzylpyrimidin-4-one;
1-(Pyrid-4-ylmethyl)-2-(8-(4-chlorophenyl)oct-1-yl)thiopyrimidin-4-one;
1-(2-(Pyrid-2-yl)ethyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(Pyrid-3-yl)ethyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
1-(2-(Pyrid-3-yl)ethyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4one;
1-(2-(Pyrid-4-yl)ethyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
1-(2-(Pyrid-4-yl)ethyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
1-(2-Methylprop-1-yl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-Phenylsulfonyl-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
1-Benzyl-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
1-Benzyl-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
1-Benzyl-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
1-Benzyl-2-(8-phenyloct-1-yl)thio-5-((2-methylpyrid-5-yl)methyl)pyrimidin-4-one;
1-Benzyl-2-(8-phenyloct-1-yl)thio-5-((2-methoxypyrid-4-yl)methyl)pyrimidin-4-one;
1-Benzyl-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
1-(2-Thienylmethyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2,2-Dimethylprop-1-yl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(1-Piperidino)ethyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Hydroxyethyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Hydroxyethyl)-2-(8-(4chlorophenyl)oct-1-yl)thio-5-benzylpyrimidin-4-one;
1-Ethyl-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Fur-2-ylmethyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Fur-2-ylmethyl)-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-benzylpyrimidin-4-one;
1-Methyl-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-bromopyrimidin-4-one;
1-Methyl-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
1-Methyl-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
1-Methyl-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one
1-Methyl-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-Methyl-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-benzylpyrimidin-4-one;
1-Phenyl-2-(8-(4chlorophenyl)oct-1-yl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
1-Methylsulfonyl-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
1-Benzyl-2-(8-phenyloct-1-yl)oxy-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
1-(2-Methoxyethyl)-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Phenylprop-1-yl)-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(5-Hydroxypent-1-yl)-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(pyrid-2-ylmethyl)-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Pyrid-3-ylmethyl)-2-benzylthio-5-((-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
1-(Pyrid-4-ylmethyl)-2-benzylthio-5-benzylpyrimidin-4-one;
1-(2-(Pyrid-2-yl)ethyl)-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(Pyrid-3-yl)ethyl)-2-benzylthio-S-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(Pyrid-4-yl)ethyl)-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(Pyrid-4-yl)ethyl)-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-benzylthio-5-((2-methoxypyrid-4-yl)methyl)pyrimidin-4-one;
1-Benzyl-2-benzylthio-5-((2-methoxypyrid-4-yl)methyl)pyrimidin-4-one;
1-(2-Thienylmethyl)-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2,2-Dimethylprop-1-yl)-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Fur-2-ylmethyl)-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-Methyl-2-benzylthio-5-((2-methoxypyrid-4-yl)methyl)pyrimidin-4one;
1-Benzyl-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-Methyl-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1 Benzyl-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-(pyrid-4-yl)pyrimidin-4-one;
1-Benzyl-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Fur-2-ylmethyl)-2-(2-phenylethyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Fluorobenzyl)-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(8-Phenyloctyl)-2-benzylthio-5-(pyrid-5-ylmethyl)pyrimidin-4-one;
1-(9-Phenylnonyl)-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-Benzyl-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-Benzyl-2-benzylthio-5-((1-methylpyrazol-4-yl)methyl)pyrimidin-4-one;
1-Benzyl-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2,2-Dimethylprop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Fur-2-ylmethyl)-2-(4-methylbenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Fur-2-ylmethyl)-2-(2-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4one;
1-(Fur-2-ylmethyl)-2-(4-chlorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Fur-2-ylmethyl)-2-(3-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Fur-2-ylmethyl)-2-(3-chlorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-Methyl-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-((R)-Tetrahydofuran-2-ylmethyl)-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-((S)-Tetrahydofuran-2-ylmethyl)-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-Fluorobenzyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-Bromobenzyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(6-(4-Fluorophenyl)hex-1-yloxy)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenoxyethyl)-2-(3,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(5-Phenylpent-1-yloxy)prop-1-yl)-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(9-Phenylnonyl)-2-furfurylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(9-Phenylnonyl)-2-(thiazol-2-ylmethyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(9-Phenylnonyl)-2-(thien-2-ylmethyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(9-Phenylnonyl)-2-(3,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(2-Pent-1-ylphenyl)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(3-Pent-1-ylphenyl)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(4-Bromophenyl)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(5-Methylfuran-2-ylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(2-Chlorophenyl)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(Thien-2-yl)ethyl)-2-(3,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-(2,3,4-trifluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-(2,3,5-trifluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-(2,4,6-trifluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-(2,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;,
1-(2-Phenylethyl)-2-(2-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-furfurylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-(thien-2-ylmethyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-(3,4,5-trifluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-(3,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-(3,5-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-(3-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-(4-fluorobenzylithio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-(1-phenylethyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(4-Methoxyphenyl)ethyl)-2-(3,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(4-Pent-1-ylphenyl)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Cycloprop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Dodec-1-yl)-2-(3,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-Ethyl-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(-Methylethyl)-2-(4-fluorobenzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Undec-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Undec-1-yl)-2-(4-fluorobenzyl)thio-5-(2-oxopyrimid-5-ylmethyl)pyrimidin-4-one;
1-Benzyl-2-benzylthio-5-(2-methoxypyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-(3,4-difluorobenzyl)thio-5-(2-methoxypyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Furan-2-ylmethyl)-2-(3,4-difluorobenzyl)thio-5-(2-methoxypyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Undec-1-yl)-2-(4-fluorobenzyl)thio-5-(2-methoxypyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Undec-1-yl)-2-(4-fluorobenzyl)thio-5-(2-ethoxypyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Undec-1-yl)-2-(4-fluorobenzyl)thio-5-(2-methylpyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethyl)-2-(4-fluorobenzyl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
1-(Undec-1-yl)-2-(4-fluorobenzyl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
1-(Undec-1-yl)-2-(4-fluorobenzyl)thio-5-(1-methyl-2-oxopyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Undec-1-yl)-2-(4-fluorobenzyl)thio-5-(1-benzyl-2-oxopyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Undec-1-yl)-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-Methyl-2-(4-fluorobenzyl)thio-5-(2-methoxypyrimid-5-ylmethyl)pyrimidin-4-one;
1-Methyl-2-(4-fluorobenzyl)thio-5-(2-oxopyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-Acetylphenyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(Non-1-yloxy)phenyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(Dec-1-yl)phenyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-Methyl-2-(4-fluorobenzyl)thio-5-(1-undecyl-2-oxopyrimid-5-ylmethyl)pyrimidin-4-one;
1-Phenyl-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-Phenyl-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-(Non-1-yloxyphenyl))-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-Iodophenyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-(Hex-1-yl)phenyl)-2-(4-fluorobenzyl)thio—(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-(Dec-1-yl)phenyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-Ethoxycarbonylmethyl-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Ethoxycarbonylprop-1-yl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Ethoxycarbonylprop-1-yl)-2-benzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Ethoxycarbonylprop-1-yl)-2-(3,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Ethoxycarbonylprop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(5-Ethoxycarbonylpent-1-yl)-2-(3,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(1-(Ethoxycarbonyl)cycloprop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-Fluorobenzyloxycarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-Ethoxycarbonylmethyl-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(1-(Methoxycarbonyl)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one
1-(trans-4-(Methoxycarbonyl)cyclohex-1-ylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(trans-4-(Methoxycarbonyl)cyclohex-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4one;
1-(3-Ethoxycarbonylprop-1-yl)-2-(4-fluorobenzyl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
1-(Ethoxycarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(2-methoxypyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-(Ethoxycarbonyl)benzyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-Methoxycarbonylbenzyl)-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-(pyrid-3-ylmethyl)-pyrimidin-4-one;
1-(3-Carboxyprop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-Carboxymethyl-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Carboxyprop-1-yl)-2-(4-fluorobenzyl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
1-(3-Carboxyprop-1-yl)-2-(3,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(5-Carboxypent-1-yl)-2-(3,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-Carboxybenzyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)-2-thiouracil;
1-(4-Carboxycyclohex-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)-2-thiouracil;
1-(3-Ethoxycarbonylphenyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Ethoxycarbonylphenyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Carboxyphenyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Carboxyphenyl)2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-Ethoxycarbonylphenyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4 one;
1-(4-Ethoxycarbonylphenyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-Carboxyphenyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-Carboxyphenyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(5-(Ethoxycarbonyl)fur-2-yl)-2-4fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Ethoxycarbonyl-4-iodobenzyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(Hept-1-yloxy)-4-methoxycarbonylbenzyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(Hept-1-yloxy)-4-methoxycarbonylbenzyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Carboxy-4-(hept-1-yloxy)benzyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(Hept-1-yloxy)4-carboxybenzyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Methoxycarbonyl-4-hydroxybenzyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Methoxycarbonylbenzyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Carboxybenzyl)-2-(4-fluorobenzylithio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3,4-Di-(methoxycarbonyl)benzyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-Carboxamidomethyl-2-(8-(4-chlorophenyl)oct-1-yl)thio-5-(pyrid-3-ylmethyl)pyrimidin-4-one;
1-Dimethylaminocarbonylmethyl-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-Carboxamidomethyl-2-benzylthio-5-((2-methoxypyrid-4-yl)methyl)pyrimidin-4-one;
1-(3-(Octadec-1ylaminocarbonyl)prop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(Octadec-9-(Z)-en-1ylaminocarbonyl)prop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(Octadec-9-(E)-en-1ylaminocarbonyl)prop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(N-Dodec-1yl-N-methylaminocarbonyl)prop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(N-Non-1-yl-N-methylaminocarbonyl)prop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-(Pent-1-ylaminocarbonyl)benzyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(1-(6-(4-Fluorophenyl)hex-1-ylaminocarbonyl)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(11-Dimethylaminoundec-1-ylaminocarbonyl)prop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(3-Ethoxyprop-1ylaminocarbonyl)prop-1-yl)-2-(3,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(5-(Methoxycarbonyl)-5-(benzykloxycarbonylamino)pent-1ylaminocarbonyl)prop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(5-(Methoxycarbonyl)pent-1ylaminocarbonyl)prop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(Hex-1ylaminocarbonyl)prop-1-yl)-2-(3,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(5-(t-Butoxycarbonylamino)pent-1ylaminocarbonyl)prop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(6-(t-Butoxycarbonylamino)hex-1ylaminocarbonyl)prop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(Dec-1ylaminocarbonyl)prop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(Dec-1 ylaminocarbonyl)prop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(Hept-1ylaminocarbonyl)prop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(Hex-1ylaminocarbonyl)prop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(Non-1 ylaminocarbonyl)prop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(Oct-1ylaminocarbonyl)prop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(Pent-1ylaminocarbonyl)prop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(N-Hex-1yl-N-methylaminocarbonyl)prop-1-yl)-2-(3,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(5-(2-methoxyethylaminocarbonyl)pent-1-yl)-2-(3,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(5-(2-Phenylethylaminocarbonyl)pent-1-yl)-2-(3,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(5-(But-1-ylaminocarbonyl)pent-1-yl)-2-(3,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(5-(N-(2-Phenylethyl)-N-methylaminocarbonyl)pent-1-yl)-2-(3,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(5-(N-But-1-yl-N-methylaminocarbonyl)pent-1-yl)-2-(3,4-difluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-((R)-1-(Hex-1-ylaminocarbonyl)ethylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-((S)-1-(Hex-1-ylaminocarbonyl)ethylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-((S)-2-(Hex-1-ylaminocarbonyl)pyrrolidin-1-ylcarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(1-Pyrrolidinocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Butoxyprop-1-ylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(6-Hydroxyhex-1-ylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(6-(4-Fluorophenyl)hex-1-ylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Tridec-1-ylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Tetradec-1-ylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Octadec-1-ylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-S-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Octadec-9-(Z)-en-1--ylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Octadec-9-(E)-en-1ylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Dec-1-ylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Dodec-1-ylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one
1-(Hept-1-ylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Oct-1-ylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Undec-1-ylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Hydroxyethylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Methoxyethylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Phenylethylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(4-Pent-1-ylphenyl)ethylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Hex-1-ylaminocarbonylmethylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(N-(Dodec-1-yl)-N-methylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(N-(2-Phenylethyl)-N-methylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-(But-1-ylaminocarbonyl)cyclohex-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-(Hex-1-ylaminocarbonyl)cyclohex-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-(2-Methoxyethylaminocarbonyl)cyclohex-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(1-(6-(4-Fluorophenyl)hex-1-yl)aminocarbonyl)cycloprop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(1-(Non-1-ylaminocarbonyl)cycloprop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-((R)-1-(Non-1-ylaminocarbonyl)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(1-(Dimethylamino)undec-1-ylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(6-(4-Fluorophenyl)hex-1-yloxy)ethylaminocabonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(5-(Methoxycarbonyl)-5-(benzyloxycarbonylamino)pent-1-ylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(5-(Methoxycarbonyl)pent-1-ylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(Non-1-ylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-Dimethylaminocarbonylmethyl-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(N-(2-Hydroxyethyl)-N-methylaminocabonylmethyl)-2-(4-fluorobenzylthio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(trans-4-(4-Fluorobenzylaminocarbonyl)cyclohex-1-ylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(trans-4-(Pent-1-ylaminocarbonyl)cyclohex-1-ylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4one;
1-(3-(Hex-1ylaminocarbonyl)prop-1-yl)-2-(4-fluorobenzyl)thio-5-((1-methyl-2-oxo-pyrid-4-yl)methyl)pyrimidin-4-one;
1-(N-(N′-Hex-1-yl-N′-methylaminocarbonylmethyl)-N-methylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(N-(N′-Hex-1-ylaminocarbonylmethyl)-N-methylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(N-(N′-Hex-1-yl-N′-methylaminocarbonylmethyl)aminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-Phenylaminocarbonylmethyl-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4one;
1-(4-Methoxycarbonylbenzylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-S-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(N-Benzylaminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one,
1-(N,N-Di-(but-1-yl)aminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(pyrimrid-5-ylmethyl)pyrimidin-4-one;
1-(N-Methyl-N-(dodec-1-yl)aminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(2methoxypyrimid-5-ylmethyl)pyrimidin-4-one;
1-(N-Methyl-N-(oct-1-yl)aminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(2-methoxypyrimid-5-ylmethyl)pyrimidin-4-one;
1-(N-Methyl-N-(oct-1-yl)aminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(2-methoxypyrimid-5-ylmethyl)pyrimidin-4-one;
1-(N-Methyl-N-(oct-1-yl)aminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(2-benzyloxypyrimid-5-ylmethyl)pyrimidin-4-one;
1-(N-Methyl-N-(dodec-1-yl)aminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(2-oxopyrimid-5-ylmethyl)pyrimidin-4-one;
1-(N-Methyl-N-(oct-1-yl)aminocarbonylmethyl)-2-(4-fluorobenzyl)thio-5-(2-oxopyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(N-(Hept-1-yl)-N-methylaminocarbonyl)phenyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(N-Ethyl-N-methylaminocarbonyl)phenyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-(Prop-1-ylaminocarbonyl)phenyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one,
1-(4-(But-1-ylaminocarbonyl)phenyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-(Hex-1-yloxycarbonyl)phenyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one,
1-(4-Methylaminocarbonylbenzyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-Methylaminocarbonyl-4-(hept-1-yloxy)benzyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(t-Butoxycarbonylamino)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one,
1-(2-(Trifluoroacetylamino)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(Benzoylamino)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(Hex-1-ylcarbonylamino)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(5-Phenylpent-1-ylcarbonylamino)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(Hept-1-ylcarbonylamino)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-Acetylaminoethyl)-2-(8-(4-chlorophenyl)-8-oxooct-1-yl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(4-(tert-Butoxycarbonylamnino)but-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(Ethoxycarbonylamino)prop-1-yl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(3-(Benzylaminocarbonylamino)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(Dodec-1-ylaminocarbonylamino)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(Hept-1-ylaminocarbonylamino)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(Oct-1-ylaminocarbonylamino)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(2-Thien-2-ylethylaminocarbonylamino)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(1,1,3,3-Tetramethylbut-1-ylaminocarbonylamino)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(4-(butoxycarbonyl)phenylaminocarbonylamino)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(4-(1-Methylethyl)phenylaminocarbonylamino)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(4-Methylphenylaminocarbonylamino)ethyl)-2-(4-fluorobenzyl)thio-5-pyrimid-5-ylmethyl)pyrimidin-4-one;
1-(2-(4-Ethoxyphenylaminocarbonylamino)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one;
and
1-(2-(4-Phenoxyphenylaminocarbonylamino)ethyl)-2-(4-fluorobenzyl)thio-5-(pyrimid-5-ylmethyl)pyrimidin-4-one.

407 more elements

A process for preparing a compound of formula (I) which process comprises:

(a) treating a compound of formula (IIA):
609
in which R1 and Z are as hereinbefore defined;
with a compound of formula (III):
R2YCH2L1 (III)
in which Y and R2 are as hereinbefore defined and L1 is a leaving group e.g. bromine or iodine:
to give a compound of formula (IA):
610
in which Z, Y, R1 and R2 are as hereinbefore defined and X is S;
or
(b) treating a compound of formula (IV):
611
in which Z and R1 are as hereinbefore defined and L2 is a leaving group, e.g. halogen such as chlorine or bromine, alkylthio such as methylthio, or —NHNO2, with a compound of formula (V):
R2YCH2XH (V)
in which X, Y and R2 are as hereinbefore defined:
advantageously at an elevated temperature, in a solvent such as pyridine, to give a compound of formula (IA);
and thereafter, and if so desired:
treating a compound of formula (IA) form (a) or (b) above with a compound of formula (VI):
R7WL1 (VI)
in which L1, W and R7 are as hereinbefore defined;
to give a compound of formula (1B):
612
in which X, Y, Z, R1 and R2 are as hereinbefore defined and WR7 is as hereinbefore defined, other than —H;
(c) treating a compound of formula (IIB):
613
in which W is a bond, Z and R1 are as hereinbefore defined and R7 are as hereinbefore defined, other then H,
with a compound of formula (Ill) as hereinbefore defined, to obtain a compound of formula (IB);
and, thereafter and if so desired;
treating a compound of formula (IA) or (IB) in which X is S with a compound of formula (V):
R2YCH2OH (VII)
in which Y and R2 are as hereinbefore defined;
to give a corresponding compound of formula (I) in which X is O;
or
(d) for a compound of formula (I) in which Z is a bond and R1 represents halogen, treating a compound of formula (VIII):
614
in which W, Y, R2, and R7 are as hereinbefore defined;
with a halogenating agent, preferably with bromine to form a compound of formula (I) in which Z is a bond and R1 is bromine, the reaction being advantageously effected in a solvent such as dichloromethane.

34 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/115,452Filed 2 Apr 2002
Priority: GB 9723352.26 Nov 1997
Published: 29 Aug 2002
Term ends: Not estimatedThe source records don’t support an estimate.

Classification24 codes

C07D 239/56
Two or more oxygen, sulphur or nitrogen atoms: one oxygen atom and one sulfur atom
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics
A61P 9/02
Drugs for disorders of the cardiovascular system: non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
A61P 9/10
Drugs for disorders of the cardiovascular system: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary…

Family

Application09/530,713Division · filed 28 Jun 2000
Application09/530,713A 371 of international · filed 28 Jun 2000
Application10/115,452Division · filed 2 Apr 2002
US 6,417,192 B1Related patent
US 2002/0120139 A1This patent

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

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A compounds of formula (I):

608
in which:
Z is a bond and R1 is halogen;
or
Z is CR3R4, where R3 and R4 are each hydrogen or C(1-4)alkyl, or R3 and R4 together with the intervening carbon atom form a C(3-6)cycloalkyl ring;
and
R1 is an aryl or heteroaryl group, optionally substituted by 1, 2, 3 or 4 substituents selected from C(1-18)alkyl, C(1-18)alkoxy, C(1-18)alkylthio, arylC(1-18)alkoxy, oxo, hydroxy, halogen, CN, COR5, COOR5, CONR5R6, NR5COR6, SO2NR5R6, NR5SO2R6, NR5R6, mono to perfluoro-C(1-4)alkyl and mono to perfluoro-C(1-4)alkoxy;
X is O or S;
Y is a group of formula -A1-A2-A3- in which A1 and A3 each represent a bond or a straight chain or branched C(1-10)alkylene group and A2 represents a bond or O, S, SO, SO2, CO, C═CH2, C═CH, C≡C, CONH, NHCO, or CR5R6, providing that when A2 is O, S, SO, SO2 or CONH, A3 contains at least two carbon atoms linking the A2 group and the CH2 group in formula (I);
R2 is an aryl or heteroaryl group, optionally substituted by 1, 2, 3 or 4 substituents selected from the substituents hereinbefore defined for R1, as well as aryl and arylC(1-4)alkyl;
W is a bond and R7 is hydrogen;
or
W is SO2 or a bond;
and
R7 is R1 or a hydrocarbyl group which hydrocarbyl group may be optionally interupted within the carbon chain by a group selected from O, COO, OCO, CO, CONR8, NR8CO, NR8CONR9, NR8COO, OCONR8, and NR8, and which hydrocarbyl group may also be optionally substituted by 1 or 2 substituents selected from mono to perfluoro-C(1-4)alkyl, OR8, COOR8, CONR8R9, NR8COR9, NR8CONR9R10, NR8COOR9, OCONR8R9, NR11R12 and R1;
R5 and R6 are independently hydrogen or C(1-20)alkyl, for instance C(1-4)alkyl (e.g. methyl or ethyl);
R8, R9 and R10 are independently selected from hydrogen, C(1-20)alkyl (for instance C(1-15)alkyl), (which may optionally be fluorinated, including up to perfluorinated on the terminal 1 to 3 carbon atoms), C(1-20)alkenyl (preferably C(12-18)alkenyl), aryl, arylC(1-10)alkyl, C(1-10)alkoxyC(1-10)alkyl, or aryloxyC(1-10)alkyl and in which an aryl group may have one or two substituents selected from halogen, C(1-20)alkyl, C(1-20)alkoxy, aryloxy and COOC(1-20)alkyl;
and
R11 and R12 are independently selected from one of the values hereinbefore defined for R8 and R9 or R11 and R12 together with the nitrogen atom to which they are attached form a 5- to 7 membered ring optionally containing one or two further heteroatoms selected from oxygen, nitrogen and sulphur, and optionally substituted by one or two substituents selected from hydroxy, oxo, C(1-4)alkyl, phenyl, or benzyl.

16 more elements

Facts

Application

10/115,452Filed 2 Apr 2002

Priority

GB 9723352.26 Nov 1997

Published

29 Aug 2002

Term ends

Not estimatedThe source records don’t support an estimate.

Classification24 codes

C07D 239/56
Two or more oxygen, sulphur or nitrogen atoms: one oxygen atom and one sulfur atom
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics
A61P 9/02
Drugs for disorders of the cardiovascular system: non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
A61P 9/10
Drugs for disorders of the cardiovascular system: for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary…