Certain phosphonomethyl-pentanedioic acid derivatives thereof
First Claim
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1. A compound having the formula:
- ##STR8## where R is a C1 -C9 straight or branched chain alkyl, C2 -C9 straight or branched chain alkenyl group, C3 -C8 cycloalkyl, C5 -C7 cycloalkenyl, phenyl, 1-naphthyl, 2-naphthyl, or phenyl(C1 -C4 alkyl), wherein said alkyl, alkenyl, cycloalkyl, cycloalkenyl, phenyl, 1-naphthyl, 2-napthyl, or phenyl (C1 -C4 alkyl) groups are optionally substituted with a substituent selected from the group consisting of;
C3 -C8 cycloalkyl, C5 -C7 cycloalkenyl, C1 -C4 alkyl, C1 -C4 alkenyl, hydroxy, halo, hydroxyl, nitro, trifluoromethyl, C1 -C6 straight or branched chain alkyl or alkenyl, C1 -C4 alkoxy, C1 -C4 alkenyloxy, phenoxy, benzyloxy, amino, and Ar1, where Ar1 is selected from the group consisting of 1-naphthyl, 2-naphthyl, and phenyl, and where Ar1 has one to three substituents which are independently selected from the group consisting of hydrogen, halo, hydroxyl, nitro, trifluoromethyl, C1 -C6 straight or branched alkyl or alkenyl, C1 -C4 alkoxy or C1 -C4 alkenyloxy, phenoxy, benzyloxy, and amino;
or a pharmaceutically acceptable salt, hydrate or a mixture thereof.
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Abstract
The present disclosure relates to dipeptidase inhibitors, and more particularly, to N-Acetylated α-Linked Acidic Dipeptidase (NAALADase) enzyme inhibitors which are proposed as novel agents for the treatment of prostate cancer. NAALADase is enzyme which is a membrane-bound metalloprotease which hydrolyzes the dipeptide, N-acetyl-L-aspartate-L-glutamate (NAAG) to yield glutamate and N-acetylaspartate. The compounds of the present invention include phosphinic acid derivatives that inhibit NAALADase enzyme activity and which have been found useful for inhibiting the growth of prostate cancer cells.
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Citations
11 Claims
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1. A compound having the formula:
- ##STR8## where R is a C1 -C9 straight or branched chain alkyl, C2 -C9 straight or branched chain alkenyl group, C3 -C8 cycloalkyl, C5 -C7 cycloalkenyl, phenyl, 1-naphthyl, 2-naphthyl, or phenyl(C1 -C4 alkyl), wherein said alkyl, alkenyl, cycloalkyl, cycloalkenyl, phenyl, 1-naphthyl, 2-napthyl, or phenyl (C1 -C4 alkyl) groups are optionally substituted with a substituent selected from the group consisting of;
C3 -C8 cycloalkyl, C5 -C7 cycloalkenyl, C1 -C4 alkyl, C1 -C4 alkenyl, hydroxy, halo, hydroxyl, nitro, trifluoromethyl, C1 -C6 straight or branched chain alkyl or alkenyl, C1 -C4 alkoxy, C1 -C4 alkenyloxy, phenoxy, benzyloxy, amino, and Ar1, where Ar1 is selected from the group consisting of 1-naphthyl, 2-naphthyl, and phenyl, and where Ar1 has one to three substituents which are independently selected from the group consisting of hydrogen, halo, hydroxyl, nitro, trifluoromethyl, C1 -C6 straight or branched alkyl or alkenyl, C1 -C4 alkoxy or C1 -C4 alkenyloxy, phenoxy, benzyloxy, and amino;
or a pharmaceutically acceptable salt, hydrate or a mixture thereof. - View Dependent Claims (4, 6, 7, 9, 10, 11)
- ##STR8## where R is a C1 -C9 straight or branched chain alkyl, C2 -C9 straight or branched chain alkenyl group, C3 -C8 cycloalkyl, C5 -C7 cycloalkenyl, phenyl, 1-naphthyl, 2-naphthyl, or phenyl(C1 -C4 alkyl), wherein said alkyl, alkenyl, cycloalkyl, cycloalkenyl, phenyl, 1-naphthyl, 2-napthyl, or phenyl (C1 -C4 alkyl) groups are optionally substituted with a substituent selected from the group consisting of;
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2. A compound selected from the group consisting of:
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2- methylhydroxyphosphinyl!methyl!pentanedioic acid; 2- ethylhydroxyphosphinyl!methyl!pentanedioic acid; 2- propylhydroxyphosphinyl!methyl!pentanedioic acid; 2- butylhydroxyphosphinyl!methyl!pentanedioic acid; 2- cyclohexylhydroxyphosphinyl!methyl!pentanedioic acid; 2- phenylhydroxyphosphinyl!methyl!pentanedioic acid; 2- (phenylmethyl)hydroxyphosphinyl!methyl!pentanedioic acid; 2- ((2-phenylethyl)methyl)hydroxyphosphinyl!methyl!pentanedioic acid; 2- ((3-phenylpropyl)methyl)hydroxyphosphinyl!methyl!pentanedioic acid; 2- ((3-phenylbutyl)methyl)hydroxyphosphinyl!methyl!pentanedioic acid; 2- ((2-phenylbutyl)methyl)hydroxyphosphinyl!methyl!pentanedioic acid; 2- (4-phenylbutyl)hydroxyphosphinyl!methyl!pentanedioic acid; 2- (aminomethyl)hydroxyphosphinyl!methyl!pentanedioic acid;
or apharmaceutically acceptable salt, hydrate or a mixture thereof. - View Dependent Claims (5, 8)
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3. A compound selected from the group consisting of:
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2- methylhydroxyphosphinyl!methyl!pentanedioic acid; 2- ethylhydroxyphosphinyl!methyl!pentanedioic acid; 2- propylhydroxyphosphinyl!methyl!pentanedioic acid; 2- phenylhydroxyphosphinyl!methyl!pentanedioic acid; 2- phenylmethylhydroxyphosphinyl!methyl!pentanedioic acid;
or a pharmaceutically acceptable salt, hydrate or a mixture thereof.
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Specification
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Current AssigneeEisai Incorporated (Eisai Medical Research Incorporated)
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Original AssigneeGuilford Pharmaceuticals Inc. (Eisai Medical Research Incorporated)
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InventorsSlusher, Barbara S., Jackson, Paul F.
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Primary Examiner(s)Rotman, Alan L.
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Application NumberUS08/665,776Time in Patent Office470 DaysField of Search562/8, 562/12, 514/75US Class Current514/75CPC Class CodesC07F 9/301 Acyclic saturated acids whi...C07F 9/4075 Esters with hydroxyalkyl co...C07F 9/4465 of aliphatic aminesC07F 9/58 Pyridine ringsC07F 9/65515 the oxygen atom being part ...C07F 9/6552 the oxygen atom being part ...
