US 7,247,639 B2Granted

A1 adenosine receptor antagonists

AssigneeEndacea, Inc.

InventorsConstance N. Wilson, John J. Partridge

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Abstract

The present invention provides novel adenosine receptor antagonists, more particularly, A1 adenosine receptor antagonists of formula (I). Pharmaceutical compositions comprising an A1 adenosine receptor antagonist of formula (I) and a pharmaceutically acceptable carrier are further provided. Compositions also include diagnostic assay-type probes comprising a novel A1 adenosine receptor antagonist of formula (I) that is labeled or conjugated with radioactive or non-radioactive material. Methods for treating A1 adenosine receptor related disorders comprising administering an A1 adenosine receptor antagonist of formula (I) are also disclosed. The novel A1 adenosine receptor antagonist compositions of formula (I) find further use in diagnostic and imaging methods. wherein R3 is Alk14ArR16, and wherein Alk14 is C1-8 straight or branched alkylene or alkenylene.

Claims4

Dependent claims

A compound of formula (I):

wherein;
R1 is C1-8 straight or branched alkyl optionally substituted with one or more OR5, NR6R7, or halogen groups,
wherein;
R5 and R6 are independently H, or C1-8 straight or branched alkyl;
R7 is H, C1-8 straight or branched alkyl, or Alk1-OH,
wherein;
Alk1 is C1-8 straight or branched alkylene;
R2 is H, C1-8 alkyl, Alk2COOH, Alk3COOR8, Alk4CONR9R10, Alk5OH, Alk6SO3H, Alk7PO3H2, Alk8OR11, Alk9OH or Alk10NR12R13, or, when R3 is (CH2) q(C6H4)Q, R2is as defined above or is Alk11 N(CH3)Alk12OH;
and when R3 is other than (CH2)q(C6H4)Q, R2 is as defined above or is Alk13NR14R15;
wherein;
Alk2 through Alk13 are independently C1-8 straight or branched alkylene or alkenylene;
q is an integer ranging from 1 to 8;
Q is H, OH, NH2, (CH2)t OH, or R13aCOOH, wherein t is an integer ranging from 1 to 8;
R8 through R13 are independently H, or C1-8 straight or branched alkyl;
R13a is C1-8 straight or branched alkylene;
R14 is H, CH3, or (CH2)p1CH3;
R15 is H, CH3, (CH2)p2CH3 or (CH2)mOH,
wherein;
p1 and p2 are independently integers from 1 to 7, and m is an integer from 1 to 8;
R3 is Alk14ArR16,
wherein;
Alk14 is C1-8 straight or branched alkylene or alkenylene;
Ar is a 5- or 6-member aromatic ring containing 0 to 4 heteroatoms selected from N, O, and S, or is a bicyclic 9- or 11-member aromatic ring containing 0 to 6 heteroatoms selected from N, O, and S;
R16 is H, OH, OR13b, NO2, NH2, CN, Alk15OH, Alk16NH2, NR17R18, NR19COR19a, Alk17COOR19b, SO2R19c, SO3H, PO3H2 or halogen;
wherein;
Alk15 through Alk17 are independently C1-8 straight or branched alkylene or alkenylene;
R13b is H, or C1-8 straight or branched alkyl;
R17, through R19 and R19a through R19c are independently H, an aromatic group, or C1-8 straight or branched alkyl;
R4 is
wherein;
r is an integer from 1 to 20;
R20 is SO3H, PO3H2, halogen, OR13c, COOR13d, NO2, NR21R22, NR23COR23a,
Alk18COOR19d, SO2R19e or Alk18NR24R25 and when R3 is other than
(CH2)q(C6H4)Q, R20 is as defined above or is H, OH, NH2 Alk19OH, Alk20NH2, or Alk21COOH;
wherein;
Alk19 through Alk21 are independently C1-8 straight or branched alkylene or alkenylene;
R13c and R13d are independently C1-8 straight or branched alkyl;
R19d and R19e are independently H, an aromatic group or C1-8 straight or branched alkyl;
R21, through R25 and R23a are independently H, an aromatic group or C1-8 straight or branched alkyl;
and salts thereof.

37 more elements

The compound of formula (I) which is:

3-[2-[4-(5-aminopentyl-3-aminocarbonylpropanoyl)]aminophenyl]ethyl]-8-benzyl-7-(2,2-diethylamino]ethyl-1-propylxanthine,
3-[2-[4-(5-aminopentanoyl)aminophenyl]ethyl]-8-benzyl-7-(2,2-diethylamino) ethyl-1-propylxanthine,
3-[4-(4-aminophenyl)butyl]-8-benzyl-7-(2-ethylamino)ethyl-1-pentylxanthine,
3-[4-(2-aminophenyl)butyl]-8-benzyl-7-(2-ethylamino)ethyl-1-propylxanthine,
3-[4-(3-aminophenyl)butyl]-8-benzyl-7-(2-ethylamino)ethyl-1-propylxanthine,
3-[2-(3-acetaminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(pyridazine-5-yl)methyl]xanthine,
3-[2-(4-acetaminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-(3-methylsulfonobenzyl) xanthine,
3-[2-(4-aminophenyl)ethyl]-8-benzyl-7-(2-ethylamino)ethyl-1-pentylxanthine,
3-[2-(4-aminophenyl)ethyl]-8-benzyl-7-(2,2-diethylamino)ethyl-1-propylxanthine,
3-[2-(4-aminophenyl)ethyl]-8-benzyl-7-[2-methyl(2-hydroxyethyl)amino]ethyl-1-propylxanthine,
3-[2-(4-aminophenyl)ethyl]-8-benzyl-7-(2-methylamino)ethyl-1-propylxanthine,
3-[2-(4-aminophenyl)ethyl]-8-benzyl-7-(2,2-dimethylamino)ethyl-1-propylxanthine,
3-[2-(4-aminophenyl)ethyl]-8-(3-chlorobenzyl)-7-[2-ethyl(2-hydroxyethyl)amino]ethyl- 1-propylxanthine,
3-[2-(2-aminophenyl)ethyl]-8-benzyl-1-(3-dimethylaminopropyl)-7-(2,2-diethylamino) ethylxanthine,
3-[2-(2-aminophenyl)ethyl]-8-benzyl-1-(3-dimethylaminopropyl)-7-(2-ethylamino) ethylxanthine,
3-[2-(3-aminophenyl)ethyl]-1-butyl-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-8-[(pyridazin-4-yl)methyl]xanthine,
3-[2-(4-amino-3-chlorophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8[(pyridazin-4-yl)methyl]xanthine
3-[2-(4-amino-2-chlorophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(pyridazin-4-yl)methyl]xanthine,
3-[2-(4-amino-2-fluorophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-pyrrol-3-yl)methyl]xanthine,
3-[2-(3-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(1H-1,3,4-triazol-5-yl)methyl]xanthine,
3-[2-(2-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(1H-1,2,4-triazol-5-yl)methyl]xanthine,
3-[2-(3-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-8-[(1,2,4-oxadiazol-5-yl)methyl]-1-propylxanthine,
3-[2-(4-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(oxazol-2-yl)methyl]xanthine,
3-[2-(2-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-8-[(isoxazol-4-yl)methyl]-1-propylxanthine,
3-[2-(2-aminophenyl)ethyl]-8-[(5-chloroisoxazol-4-yl)methyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propylxanthine,
3-[2-(4-aminophenyl)ethyl]-8-(2,4-difluorobenzyl)-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propylxanthine,
3-[2-(2-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-8-[(5-fluoroisoxazol-4-yl)methyl]-1-pentyixanthine,
3-[2-(4-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-8-[(4-fluoro-2-oxazolyl)methyl]-1-propylxanthine,
3-[2-(4-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-8-[(isothiazol-3-yl)methyl]-1-propyl-xanthine,
3-[2-(3-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(pyrimidin-2-yl)methyl]xanthine,
3-[2-(2-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-8-[(4-fluoro-3-isothiazolyl)methyl]-1-propylxanthine,
3-[2-(4-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-8-[(5-fluoropyrimidin-2-yl)methyl]-1-propylxanthine,
3-[2-(3-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-8-[(1,3,4-oxadiazol-5-yl)methyl]-1-pentyixanthine,
3-[2-(4-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(1H-pyrazol-3-yl)methyl]xanthine,
3-[2-(3-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(1H-pyrazol-3-yl)methyl]xanthine,
3-[2-(4-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-pentyl-8-[(1H-pyrazol-3-yl)methyl]xanthine,
3-[2-(2-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(pyrazin-2-yl)methyl]xanthine,
3-[2-(2-aminophenyl)ethyl]-1-butyl-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-8-[(3-fluoropyrazin-2-yl)methyl]xanthine,
3-[2-(2-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-8-[(3-fluoropyrazin-2-yl)methyl]-1-pentylxanthine,
3-[2-(2-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-8-[(3-fluoropyrazin-2-yl)methyl]-1-propylxanthine,
3-[2-(4-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-pentyl-8-[(2-fluoro-1H-pyrazol-3-yl)methyl]xanthine,
3-[2-(4-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(1H-pyrrol-3-yl)methyl]xanthine,
3-[2-(2-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(1H-tetrazol-5-yl)methyl]xanthine,
3-[2-(3-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(furan-3-yl)methyl]xanthine,
3-[2-(4-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(furan-2-yl)methyl]xanthine,
3-[2-(4-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(thiophen-3-yl)methyl]xanthine,
3-[6-(4-aminophenyl)hexyl]-8-benzyl-7-(2-ethylamino)ethyl-1-pentyixanthine,
3-[6-(2-aminophenyl)hexyl]-8-benzyl-7-(2-ethylamino)ethyl-1-propylxanthine,
3-[6-(3-aminophenyl)hexyl]-8-benzyl-7-(2-ethylamino)ethyl-1-propylxanthine,
3-[6-(3-aminophenyl)hexyl]-8-benzyl-7-(2-ethylamino)ethyl-1-(3-fluoro)propylxanthine,
8-benzyl-7-(2-ethylamino)ethyl-3-[2-(3-nitrophenyl)ethyl]-1-propylxanthine,
8-benzyl-7-(2,2-diethylamino)ethyl-3-[2-(3-nitrophenyl)ethyl]-1-propylxanthine,
3-[2-(4-bromophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(4-pyridyl)methyl]xanthine,
3-[2-(4-chlorophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(4-pyridyl)methyl]xanthine,
3-[2-(2,4-diaminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-8-[(5-fluoro-2-oxazolyl)methyl]-1-propylxanthine,
7-(2,2-diethylamino)ethyl-3-(2-phenylethyl)-1-propyl-8-[(2-pyridyl)methyl]xanthine,
7-(2,2-diethylamino)ethyl-3-[2-(3-fluorophenyl)ethyl]-8-[(1,3,4-oxadiazol-5-yl)methyl]-1-propylxanthine,
7-(2,2-diethylamino)ethyl-3-[2-(3-nitrophenyl)ethyl]-1-propyl-8-[(pyridazin-4-yl)methyl]xanthine,
7-(2,2-diethylamino)ethyl-3-(2-phenylethyl)-1-propyl-8-[(1H-pyrazol-3-yl)benzyl]xanthine,
7-(2-ethylamino)ethyl-3-(2-phenylethyl)-1-propyl-8-[(2-pyridyl)methyl]xanthine,
7-(2-ethylamino)ethyl-3-[2-(3-nitrophenyl)ethyl]-8-[(1,3,4-oxadiazol-5-yl)methyl]-1-propylxanthine,
7-(2-ethylamino)ethyl-3-[2-(2-nitrophenyl)ethyl]-8-[(4-fluoro-3-isothiazolyl)methyl]-1-propylxanthine,
7-(2-ethylamino)ethyl-3-[2-(2-fluorophenyl)ethyl]-1-propyl-8-[(pyrazin-2-yl)methyl]xanthine,
7-[2-ethyl(2-hydroxyethyl)amino]ethyl-3-[2-(2-fluorophenyl)ethyl]-1-propyl-8-[(pyrazin-2-yl)methyl]xanthine,
7-[2-ethyl(2-hydroxyethyl)amino]ethyl-3-[2-(3-fluorophenyl)ethyl]-8-[(1,3,4-oxadiazol-5-yl)methyl]-1-propylxanthine,
7-[2-ethyl(2-hydroxyethyl)amino]ethyl-3-[2-(4-nitrophenyl)ethyl]-1-propyl-8-[(1H-pyrazol-3-yl)methyl]xanthine,
7-[2-ethyl(2-hydroxyethyl)amino]ethyl-3-[2-(3-nitrophenyl)ethyl]-8-[(1,3,4-oxadiazol-5-yl)methyl]-1-propylxanthine,
7-[2-ethyl(2-hydroxyethyl)amino]ethyl-3-[2-(2-nitrophenyl)ethyl]-1-propyl-8-[(1H-1,2,4-triazol-5-yl)methyl]xanthine,
7-[2-ethyl(2-hydroxyethyl)amino]ethyl-3-[2-(2-nitrophenyl)ethyl]-8-[(4-fluoro-3-isothiazolyl)methyl]-1-propylxanthine,
7-[2-ethyl(2-hydroxyethyl)amino]ethyl-3-[2-(3-nitrophenyl)ethyl]-1-propyl-8-[(pyridazin-4-yl)methyl]xanthine,
7-[2-ethyl(2-hydroxyethyl)amino]ethyl-3-[2-(3-nitrophenyl)ethyl]-8-[(1,2,4-oxadiazol-5-yl)methyl]-1-propylxanthine,
7-[2-ethyl(2-hydroxyethyl)amino]ethyl-3-(2-phenylethyl)-1-propyl-8-[(1,2,4-oxadiazol-3-yl)benzyl]xanthine,
7-[2-ethyl(2-hydroxyethyl)amino]ethyl-3-(2-phenylethyl)-1-propyl-8-[(1,3,4-oxadiazol-5-yl)benzyl]xanthine,
7-[2-ethyl(2-hydroxyethyl)amino]ethyl-3-(2-phenylethyl)-1-propyl-8-[(1H-pyrazol-3-yl)benzyl]xanthine,
7-[2-ethyl(2-hydroxyethyl)amino]ethyl-3-(2-phenylethyl)-1-pentyl-8-[(3-pyridyl)methyl]xanthine,
7-[2-ethyl(2-hydroxyethyl)amino]ethyl-3-(2-phenylethyl)-1-propyl-8-[(2-pyridyl)methyl]xanthine,
7-[2-ethyl(2-hydroxyethyl)amino]ethyl-3-(2-phenylethyl)-1-propyl-8-[(4-pyridyl)methyl]xanthine,
3-[2-(4-aminophenyl)ethyl]-8-benzyl-7-(2,2-diethylamino)ethyl-1-propylxanthine,
3-[2-(4-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-8-(4-fluorobenzyl)-1-propylxanthine, 3-[2-(4-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(3-pyridyl)methyl]xanthine,
3-[2-(4-aminophenyl)ethyl]-7-(2-ethylamino)ethyl-1-propyl-8-[(3-pyridyl)methyl]xanthine,
3-[2-(4-aminophenyl)ethyl]-7-(2,2-diethylamino)ethyl-1-propyl-8-[(3-pyridyl)methyl]xanthine,
3-[2-(4-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(thiophen-2-yl)methyl]xanthine,
3-[2-(4-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(4-thiazolyl)methyl]xanthine,
3-[2-(4-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-[(1H-tetrazol-5-yl)methyl]xanthine,
3-[2-(4-aminophenyl)ethyl]-7-(2-ethylamino)ethyl-1-propyl-8-[(1H-tetrazol-5-yl)methyl]xanthine,
3-[2-(4-aminophenyl)ethyl]-7-(2,2-diethylamino)ethyl-1-propyl-8-[(1H-tetrazol-5-yl)methyl]xanthine,
3-[2-(4-aminophenyl)ethyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-8-(4-methylsulfonyl benzyl)-1-propylxanthine,
3-[2-(4-aminophenyl)ethyl]-7-(2-ethylamino)ethyl-8-(4-methylsulfonobenzyl)-1-propylxanthine,
3-[2-(4-aminophenyl)ethyl]-7-(2,2-diethy1amino)ethy1-8-(4-methylsufonylbenzyl)-1-propylxanthine,
3-[2-(4-arminophenyl)ethyl]-8-benzyl-7-(2-ethylamino)ethyl-1-(3-methoxypropyl)xanthine,
3-[2-(4-aminophenyl)ethyl]-8-benzyl-7-(2,2-diethylamino)ethyl-1-(3-methoxypropyl)xanthine,
3-[2-(4-aminophenyl)ethyl]-8-benzyl-1-(3-dimethylaminopropyl)-7-(2-ethylamino)ethylxanthine,
3-[2-(4-aminophenyl)ethyl]-8-benzyl-7-(2,2-diethylamino)ethyl-1-(3-dimethylaminopropyl)xanthine,
3-[2-[4-(6-aminohexanoyl)aminophenyl]ethyl]-8-benzyl-7-(2,2-diethylamino)ethyl-1-propylxanthine,
3-[2-[4-(6-aminohexyl-3-aminocarbonylpropanoyl)]aminophenyl]ethyl]-8-benzyl-7-(2,2-diethylamino]ethyl-1-propylxanthine,
3-[2-(4-aminophenyl)ethyl]-8-benzyl-7-[13H, 23H-[2-ethyl(2-hydroxyethyl)amino]ethyl]-1-propylxanthine,
3-[2-(4-aminophenyl)ethyl]-8-benzyl-7-[13H, 23H-(2-ethylamino)ethyl]-1-propylxanthine,
3-[4-(4-aminophenyl)butyl]-7-[2-ethyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-(4-sulfonoxybenzyl)xanthine,
3-[4-(4-aminophenyl)butyl]-7-(2-ethylamino)ethyl-1-propyl-8-(4-sulfonoxybenzyl)xanthine,
3-[4-(4-aminophenyl)butyl]-7-(2,2-diethylamino)ethyl-1-propyl-8-(4-sulfonoxybenzyl)xanthine,
3-[4-(4-aminophenyl)butyl]-7-(2,2-dimethylamino)ethyl-1-propyl-8-(4-sulfonoxybenzyl)xanthine,
3-[2-(4-aminophenyl)ethyl]-8-benzyl-7-(2-ethylamino)ethyl-1-(3-methoxyethyl)xanthine,
3-[2-(4-aminophenyl)ethyl]-8-benzyl-7-(2,2-diethylamino)ethyl-1-(3-methoxyethyl)xanthine,
3-[2-(4-aminophenyl)ethyl]-8-benzyl-1-(3-dimethylaminoethyl)-7-(2-ethylamino)ethylxanthine,
3-[2-(4-aminophenyl)ethyl]-8-benzyl-7-(2,2-diethylamino)ethyl-1-(3-dimethylaminoethyl)xanthine, or
3-[4-(4-aminophenyl)butyl]-7-[2-methyl(2-hydroxyethyl)amino]ethyl-1-propyl-8-(4-sulfonoxybenzyl)xanthine.

103 more elements

A pharmaceutical composition comprising a compound of Formula (I):

wherein;
R1 is C1-8 straight or branched alkyl optionally substituted with one or more OR5, NR6R7, or halogen groups, and when the aromatic group of R3 is other than phenyl, R1 may also be C1-8 straight or branched alkyl
wherein;
R5 and R6 are independently H, or C1-8 straight or branched alkyl;
R7 is H, C1-8 straight or branched alkyl, or Alk1-OH,
wherein;
Alk1 is C1-8 straight or branched alkylene;
R2 is H, C1-8 alkyl, Alk2COOH, Alk3COOR8, Alk4CONR9R10, Alk5OH, Alk6SO3H, Alk7PO3H2, Alk8OR11, Alk9OH or Alk10NR12R13, or, when R3 is (CH2)q(C6H4)Q, R2 may also be Alk11N(CH3)Alk12OH;
and when R3 is other than (CH2)q(C6H4)Q, R2 may also be Alk13NR14R15;
wherein;
Alk2 through Alk13 are independently C1-8 straight or branched alkylene or alkenylene;
q is an integer ranging from 1 to 8;
Q is H, OH, NH2, (CH2)t OH, or R13aCOOH, wherein t is an integer ranging from 1 to 8;
R8 through R13, are independently H, or C1-8 straight or branched alkyl;
R13a is C1-8 straight or branched alklene;
R14 is H, CH3, or (CH2)p1CH3;
R15 is H, CH3, (CH2)p2CH3 or (CH2)mOH,
wherein;
p1 and p2 are independently integers from 1 to 7, and m is an integer from 1 to 8;
R3 is Alk14ArR16,
wherein;
Alk14 is C1-8 straight or branched alkylene or alkenylene;
Ar is a 5- or 6-member aromatic ring containing 0 to 4 heteroatoms selected from N, O, and S, or is a bicyclic 9- or 11-member aromatic ring containing 0 to 6 heteroatoms selected from N, O, and S;
R16 is H, OH, OR13b, NO2, NH2, CN, Alk15OH, Alk16NH2, NR17R18, NR19COR19a, Alk17COOR19b, SO2R19c, SO3H, PO3H2 or halogen;
wherein;
Alk15 through Alk17 are independently C1-8 straight or branched alkylene or alkenylene;
R13b is H, or C1-8 straight or branched alkyl;
R17, through R19 and R19a through R19c are independently H, an aromatic group, or C1-8 straight or branched alkyl;
R4 is
wherein;
r is an integer from 1 to 20;
R20 is SO3H, PO3H2, halogen, OR13c, COOR13d, NO2, NR21R22, NR23COR23a, Alk18COOR19d, SO2R19e or Alk18NR24R25 and when the aromatic group of R3 is other than (CH2)q(C6H4)Q, R20 may also be H, OH, NH2 Alk19OH, or Alk20NH2, or Alk21COOH;
wherein;
Alk19 through Alk21 are independently C1-8 straight or branched alkylene or alkenylene;
R13c and R13d are independently C1-8 straight or branched alkyl;
R19d and R19e are independently H, an aromatic group or C1-8 straight or branched alkyl;
R21, through R25 and R23a are independently H, an aromatic group or C1-8 straight or branched alkyl;
and
pharmaceutically acceptable salts thereof and one or more pharmaceutically acceptable carriers.

36 more elements

Dependencies are inferred from the claim text.

Facts

Application: 10/861,677Filed 4 Jun 2004 · us provisional application
Priority: 6 Jun 2003
Published: US 2005/0187226 A125 Aug 2005
Granted: 24 Jul 2007
Term ends: Not estimatedThe source records don’t support an estimate.

Classification31 codes

C07D 473/04
With oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6: two oxygen atoms
A61P 1/00
Drugs for disorders of the alimentary tract or the digestive system
A61P 3/04
Drugs for disorders of the metabolism: anorexiants; Antiobesity agents
A61P 3/10
For glucose homeostasis: for hyperglycaemia, e.g. antidiabetics