LV12232B - KNOWLEDGE PHOSPHINILATED DERIVATIVES AS NECESSARY INHIBITORS - Google Patents
KNOWLEDGE PHOSPHINILATED DERIVATIVES AS NECESSARY INHIBITORS Download PDFInfo
- Publication number
- LV12232B LV12232B LVP-98-278A LV980278A LV12232B LV 12232 B LV12232 B LV 12232B LV 980278 A LV980278 A LV 980278A LV 12232 B LV12232 B LV 12232B
- Authority
- LV
- Latvia
- Prior art keywords
- pentanedioic acid
- acid
- amino
- methyl
- oxy
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title description 45
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 title 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 374
- -1 straight or branched Chemical group 0.000 claims description 298
- 150000001875 compounds Chemical class 0.000 claims description 209
- 239000002253 acid Substances 0.000 claims description 148
- 125000003342 alkenyl group Chemical group 0.000 claims description 132
- 125000000217 alkyl group Chemical group 0.000 claims description 118
- 108090000369 Glutamate Carboxypeptidase II Proteins 0.000 claims description 92
- 102000003958 Glutamate Carboxypeptidase II Human genes 0.000 claims description 92
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 90
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 86
- 238000011282 treatment Methods 0.000 claims description 81
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 79
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 76
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 74
- 239000000203 mixture Substances 0.000 claims description 72
- 241001465754 Metazoa Species 0.000 claims description 57
- 206010060862 Prostate cancer Diseases 0.000 claims description 52
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 50
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 49
- 230000000694 effects Effects 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 46
- 125000003118 aryl group Chemical group 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 208000017497 prostate disease Diseases 0.000 claims description 41
- 229910052739 hydrogen Inorganic materials 0.000 claims description 34
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
- 230000002401 inhibitory effect Effects 0.000 claims description 28
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 28
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 26
- 150000002431 hydrogen Chemical group 0.000 claims description 26
- 239000008194 pharmaceutical composition Substances 0.000 claims description 24
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 22
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 22
- 125000001931 aliphatic group Chemical group 0.000 claims description 22
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 22
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 21
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 20
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000002837 carbocyclic group Chemical group 0.000 claims description 18
- 239000003937 drug carrier Substances 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 16
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 16
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 16
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 15
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 15
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 14
- 150000004677 hydrates Chemical class 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- CAGAVCIHAJPIJR-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]methyl]pentanedioic acid Chemical compound CP(O)(=O)CC(C(O)=O)CCC(O)=O CAGAVCIHAJPIJR-UHFFFAOYSA-N 0.000 claims description 7
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- XVXVUGZUKCQIOK-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]amino]pentanedioic acid Chemical compound CP(O)(=O)NC(C(O)=O)CCC(O)=O XVXVUGZUKCQIOK-UHFFFAOYSA-N 0.000 claims description 5
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- QIMHASXDVZXXRJ-UHFFFAOYSA-N 2-[[butyl(hydroxy)phosphoryl]amino]pentanedioic acid Chemical compound CCCCP(O)(=O)NC(C(O)=O)CCC(O)=O QIMHASXDVZXXRJ-UHFFFAOYSA-N 0.000 claims description 4
- MIINQJNPWDYQGB-UHFFFAOYSA-N 2-[[butyl(hydroxy)phosphoryl]methyl]pentanedioic acid Chemical compound CCCCP(O)(=O)CC(C(O)=O)CCC(O)=O MIINQJNPWDYQGB-UHFFFAOYSA-N 0.000 claims description 4
- SVWHVKOIOWZDQX-UHFFFAOYSA-N 2-[[hydroxy(3-phenylpropyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CCCC1=CC=CC=C1 SVWHVKOIOWZDQX-UHFFFAOYSA-N 0.000 claims description 4
- UNEONYJUQDOHQC-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]methyl]heptanedioic acid Chemical compound CP(O)(=O)CC(C(O)=O)CCCCC(O)=O UNEONYJUQDOHQC-UHFFFAOYSA-N 0.000 claims description 4
- OXVBJVMKAPKLRB-UHFFFAOYSA-N 2-[[hydroxy(phenyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)C1=CC=CC=C1 OXVBJVMKAPKLRB-UHFFFAOYSA-N 0.000 claims description 4
- UIVPEQQNMNDWDC-UHFFFAOYSA-N 2-[[hydroxy(phenyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C1=CC=CC=C1 UIVPEQQNMNDWDC-UHFFFAOYSA-N 0.000 claims description 4
- MBOCVNZPOKGSTN-UHFFFAOYSA-N 2-[[hydroxy(thiophen-3-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC=1C=CSC=1 MBOCVNZPOKGSTN-UHFFFAOYSA-N 0.000 claims description 4
- ZOQVILHRYCANIG-UHFFFAOYSA-N 2-[hydroxy(methyl)phosphoryl]oxypentanedioic acid Chemical compound CP(O)(=O)OC(C(O)=O)CCC(O)=O ZOQVILHRYCANIG-UHFFFAOYSA-N 0.000 claims description 4
- VZEGIOSPGNDJBZ-UHFFFAOYSA-N 2-[hydroxy(phenyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)C1=CC=CC=C1 VZEGIOSPGNDJBZ-UHFFFAOYSA-N 0.000 claims description 4
- BUIODKODJCEWRF-UHFFFAOYSA-N 2-[hydroxy(thiophen-3-ylmethyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC=1C=CSC=1 BUIODKODJCEWRF-UHFFFAOYSA-N 0.000 claims description 4
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
- FZQWPLKMYLFIKA-UHFFFAOYSA-N 2-[[cyclohexylmethyl(hydroxy)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1CCCCC1 FZQWPLKMYLFIKA-UHFFFAOYSA-N 0.000 claims description 3
- UAPXYLZVIGLACQ-UHFFFAOYSA-N 2-[[cyclohexylmethyl(hydroxy)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC1CCCCC1 UAPXYLZVIGLACQ-UHFFFAOYSA-N 0.000 claims description 3
- ZDECCUDWIMXEKV-UHFFFAOYSA-N 2-[[ethyl(hydroxy)phosphoryl]methyl]pentanedioic acid Chemical compound CCP(O)(=O)CC(C(O)=O)CCC(O)=O ZDECCUDWIMXEKV-UHFFFAOYSA-N 0.000 claims description 3
- LJMHTTUCPUTRMK-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-4-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1=CC=CC2=C1C=CN2 LJMHTTUCPUTRMK-UHFFFAOYSA-N 0.000 claims description 3
- BQUAJUHWMGFLGM-UHFFFAOYSA-N 2-[[hydroxy(2-naphthalen-2-ylethyl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=CC2=CC(CCP(O)(=O)CC(CCC(=O)O)C(O)=O)=CC=C21 BQUAJUHWMGFLGM-UHFFFAOYSA-N 0.000 claims description 3
- VAZDQVAVNHZARH-UHFFFAOYSA-N 2-[[hydroxy(3-phenylpropyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CCCC1=CC=CC=C1 VAZDQVAVNHZARH-UHFFFAOYSA-N 0.000 claims description 3
- CQTHZXYSMZNMKV-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]amino]decanedioic acid Chemical compound CP(O)(=O)NC(C(O)=O)CCCCCCCC(O)=O CQTHZXYSMZNMKV-UHFFFAOYSA-N 0.000 claims description 3
- XBFRRBVIIUORHE-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]amino]heptanedioic acid Chemical compound CP(O)(=O)NC(C(O)=O)CCCCC(O)=O XBFRRBVIIUORHE-UHFFFAOYSA-N 0.000 claims description 3
- XASUMCCMQXASNX-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]methyl]decanedioic acid Chemical compound CP(O)(=O)CC(C(O)=O)CCCCCCCC(O)=O XASUMCCMQXASNX-UHFFFAOYSA-N 0.000 claims description 3
- BMHKVATTWSSGNF-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]methyl]hexanedioic acid Chemical compound CP(O)(=O)CC(C(O)=O)CCCC(O)=O BMHKVATTWSSGNF-UHFFFAOYSA-N 0.000 claims description 3
- XQFINHZUZNLWMM-UHFFFAOYSA-N 2-[[hydroxy(propyl)phosphoryl]amino]pentanedioic acid Chemical compound CCCP(O)(=O)NC(C(O)=O)CCC(O)=O XQFINHZUZNLWMM-UHFFFAOYSA-N 0.000 claims description 3
- BLHBCGJHBNBAIQ-UHFFFAOYSA-N 2-[[hydroxy(pyridin-3-yl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C1=CC=CN=C1 BLHBCGJHBNBAIQ-UHFFFAOYSA-N 0.000 claims description 3
- MXFCNMASDUEDAA-UHFFFAOYSA-N 2-[butyl(hydroxy)phosphoryl]oxypentanedioic acid Chemical compound CCCCP(O)(=O)OC(C(O)=O)CCC(O)=O MXFCNMASDUEDAA-UHFFFAOYSA-N 0.000 claims description 3
- AFJIOKSJBSAYSS-UHFFFAOYSA-N 2-[hydroxy(methyl)phosphoryl]oxyheptanedioic acid Chemical compound CP(O)(=O)OC(C(O)=O)CCCCC(O)=O AFJIOKSJBSAYSS-UHFFFAOYSA-N 0.000 claims description 3
- GNZHIXUXUJTXFO-UHFFFAOYSA-N 2-[hydroxy(oxolan-2-ylmethyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1CCCO1 GNZHIXUXUJTXFO-UHFFFAOYSA-N 0.000 claims description 3
- HERVSDXHCIWYTQ-UHFFFAOYSA-N 2-[hydroxy(pyridin-3-ylmethyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1=CC=CN=C1 HERVSDXHCIWYTQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- ZQSXMDJCWKAJFZ-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-2-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2NC(CP(O)(=O)NC(CCC(=O)O)C(O)=O)=CC2=C1 ZQSXMDJCWKAJFZ-UHFFFAOYSA-N 0.000 claims description 2
- CULHXRDATVRQLL-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-3-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2C(CP(O)(=O)NC(CCC(=O)O)C(O)=O)=CNC2=C1 CULHXRDATVRQLL-UHFFFAOYSA-N 0.000 claims description 2
- YJKMOBFDMKUCIQ-UHFFFAOYSA-N 2-[[hydroxy(2-naphthalen-1-ylethyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2C(CCP(O)(=O)NC(CCC(=O)O)C(O)=O)=CC=CC2=C1 YJKMOBFDMKUCIQ-UHFFFAOYSA-N 0.000 claims description 2
- IPJWIGRYTYZQRI-UHFFFAOYSA-N 2-[[hydroxy(2-naphthalen-1-ylethyl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=C2C(CCP(O)(=O)CC(CCC(=O)O)C(O)=O)=CC=CC2=C1 IPJWIGRYTYZQRI-UHFFFAOYSA-N 0.000 claims description 2
- LQDCQAGCPHGVBY-UHFFFAOYSA-N 2-[[hydroxy(2-pyridin-3-ylethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CCC1=CC=CN=C1 LQDCQAGCPHGVBY-UHFFFAOYSA-N 0.000 claims description 2
- YBACOWWKHIWWNI-UHFFFAOYSA-N 2-[[hydroxy(2-thiophen-3-ylethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CCC=1C=CSC=1 YBACOWWKHIWWNI-UHFFFAOYSA-N 0.000 claims description 2
- FFPAEASECFDNMZ-UHFFFAOYSA-N 2-[[hydroxy(3-naphthalen-1-ylpropyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2C(CCCP(O)(=O)NC(CCC(=O)O)C(O)=O)=CC=CC2=C1 FFPAEASECFDNMZ-UHFFFAOYSA-N 0.000 claims description 2
- MKIHUHTXLFYLLI-UHFFFAOYSA-N 2-[[hydroxy(3-naphthalen-1-ylpropyl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=C2C(CCCP(O)(=O)CC(CCC(=O)O)C(O)=O)=CC=CC2=C1 MKIHUHTXLFYLLI-UHFFFAOYSA-N 0.000 claims description 2
- XWJHXJCFGVSEEM-UHFFFAOYSA-N 2-[[hydroxy(3-naphthalen-2-ylpropyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=CC2=CC(CCCP(O)(=O)NC(CCC(=O)O)C(O)=O)=CC=C21 XWJHXJCFGVSEEM-UHFFFAOYSA-N 0.000 claims description 2
- GZASHIYXNBONPS-UHFFFAOYSA-N 2-[[hydroxy(3-naphthalen-2-ylpropyl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=CC2=CC(CCCP(O)(=O)CC(CCC(=O)O)C(O)=O)=CC=C21 GZASHIYXNBONPS-UHFFFAOYSA-N 0.000 claims description 2
- VYTMVJAQFVBZGC-UHFFFAOYSA-N 2-[[hydroxy(3-pyridin-3-ylpropyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CCCC1=CC=CN=C1 VYTMVJAQFVBZGC-UHFFFAOYSA-N 0.000 claims description 2
- GUNCDQWGJVZRFS-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]amino]hexanedioic acid Chemical compound CP(O)(=O)NC(C(O)=O)CCCC(O)=O GUNCDQWGJVZRFS-UHFFFAOYSA-N 0.000 claims description 2
- VCEQZUSTJBIDMB-UHFFFAOYSA-N 2-[[hydroxy(naphthalen-1-ylmethyl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=C2C(CP(O)(=O)CC(CCC(=O)O)C(O)=O)=CC=CC2=C1 VCEQZUSTJBIDMB-UHFFFAOYSA-N 0.000 claims description 2
- DUISQPJAGXKTMQ-UHFFFAOYSA-N 2-[[hydroxy(naphthalen-2-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=CC2=CC(CP(O)(=O)NC(CCC(=O)O)C(O)=O)=CC=C21 DUISQPJAGXKTMQ-UHFFFAOYSA-N 0.000 claims description 2
- KBNKQJDRKPQRFZ-UHFFFAOYSA-N 2-[[hydroxy(naphthalen-2-ylmethyl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=CC2=CC(CP(O)(=O)CC(CCC(=O)O)C(O)=O)=CC=C21 KBNKQJDRKPQRFZ-UHFFFAOYSA-N 0.000 claims description 2
- IKWYHDVSCUMYSM-UHFFFAOYSA-N 2-[[hydroxy(propyl)phosphoryl]methyl]pentanedioic acid Chemical compound CCCP(O)(=O)CC(C(O)=O)CCC(O)=O IKWYHDVSCUMYSM-UHFFFAOYSA-N 0.000 claims description 2
- LCTSSROJTJQOLC-UHFFFAOYSA-N 2-[[hydroxy(pyridin-2-yl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)C1=CC=CC=N1 LCTSSROJTJQOLC-UHFFFAOYSA-N 0.000 claims description 2
- GOZCMXCMCACLCK-UHFFFAOYSA-N 2-[[hydroxy(pyridin-2-yl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C1=CC=CC=N1 GOZCMXCMCACLCK-UHFFFAOYSA-N 0.000 claims description 2
- HHXIKNDUYNZTHH-UHFFFAOYSA-N 2-[[hydroxy(pyridin-3-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1=CC=CN=C1 HHXIKNDUYNZTHH-UHFFFAOYSA-N 0.000 claims description 2
- YOCDHMICSMSLTQ-UHFFFAOYSA-N 2-[[hydroxy(pyridin-4-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1=CC=NC=C1 YOCDHMICSMSLTQ-UHFFFAOYSA-N 0.000 claims description 2
- PXFFOCTWVIACDR-UHFFFAOYSA-N 2-[[hydroxy(thiophen-2-yl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C1=CC=CS1 PXFFOCTWVIACDR-UHFFFAOYSA-N 0.000 claims description 2
- AWUUZLLREKFWRC-UHFFFAOYSA-N 2-[[hydroxy(thiophen-2-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1=CC=CS1 AWUUZLLREKFWRC-UHFFFAOYSA-N 0.000 claims description 2
- XDWMYTGFURHDOA-UHFFFAOYSA-N 2-[[hydroxy(thiophen-3-yl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C=1C=CSC=1 XDWMYTGFURHDOA-UHFFFAOYSA-N 0.000 claims description 2
- MOXMZILDSBXEBG-UHFFFAOYSA-N 2-[[hydroxy-[3-(oxolan-2-yl)propyl]phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CCCC1CCCO1 MOXMZILDSBXEBG-UHFFFAOYSA-N 0.000 claims description 2
- AYXQYBIHRBILHT-UHFFFAOYSA-N 2-[cyclohexylmethyl(hydroxy)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1CCCCC1 AYXQYBIHRBILHT-UHFFFAOYSA-N 0.000 claims description 2
- GIFNYTLIJTZDJM-UHFFFAOYSA-N 2-[hydroxy(1h-indol-3-ylmethyl)phosphoryl]oxypentanedioic acid Chemical compound C1=CC=C2C(CP(O)(=O)OC(CCC(=O)O)C(O)=O)=CNC2=C1 GIFNYTLIJTZDJM-UHFFFAOYSA-N 0.000 claims description 2
- BKXUVLWVHQLSFC-UHFFFAOYSA-N 2-[hydroxy(3-thiophen-3-ylpropyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CCCC=1C=CSC=1 BKXUVLWVHQLSFC-UHFFFAOYSA-N 0.000 claims description 2
- LPQJYMBUVVYRGE-UHFFFAOYSA-N 2-[hydroxy(methyl)phosphoryl]oxydecanedioic acid Chemical compound CP(O)(=O)OC(C(O)=O)CCCCCCCC(O)=O LPQJYMBUVVYRGE-UHFFFAOYSA-N 0.000 claims description 2
- WQMVADYYRIKMPQ-UHFFFAOYSA-N 2-[hydroxy(propyl)phosphoryl]oxypentanedioic acid Chemical compound CCCP(O)(=O)OC(C(O)=O)CCC(O)=O WQMVADYYRIKMPQ-UHFFFAOYSA-N 0.000 claims description 2
- QMGPVQRWSFZHJK-UHFFFAOYSA-N 2-[hydroxy(pyridin-2-ylmethyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1=CC=CC=N1 QMGPVQRWSFZHJK-UHFFFAOYSA-N 0.000 claims description 2
- CPKYVOYKTIWOHJ-UHFFFAOYSA-N 2-[hydroxy(pyridin-4-ylmethyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1=CC=NC=C1 CPKYVOYKTIWOHJ-UHFFFAOYSA-N 0.000 claims description 2
- PEGPIKSYOWTXQJ-UHFFFAOYSA-N 2-[hydroxy(thiophen-2-ylmethyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1=CC=CS1 PEGPIKSYOWTXQJ-UHFFFAOYSA-N 0.000 claims description 2
- FPWQIHZKSDTHQR-UHFFFAOYSA-N 2-[hydroxy-[2-(oxolan-2-yl)ethyl]phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CCC1CCCO1 FPWQIHZKSDTHQR-UHFFFAOYSA-N 0.000 claims description 2
- MCGYWEKQJUXSII-UHFFFAOYSA-N 2-[hydroxy-[3-(1h-indol-3-yl)propyl]phosphoryl]oxypentanedioic acid Chemical compound C1=CC=C2C(CCCP(O)(=O)OC(CCC(=O)O)C(O)=O)=CNC2=C1 MCGYWEKQJUXSII-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 14
- 150000002367 halogens Chemical class 0.000 claims 14
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 8
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/44—Amides thereof
- C07F9/4461—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4465—Amides thereof the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/6552—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a six-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/665,776 US5672592A (en) | 1996-06-17 | 1996-06-17 | Certain phosphonomethyl-pentanedioic acid derivatives thereof |
US08/775,586 US5795877A (en) | 1996-12-31 | 1996-12-31 | Inhibitors of NAALADase enzyme activity |
US08/778,733 US5863536A (en) | 1996-12-31 | 1996-12-31 | Phosphoramidate derivatives |
US08/858,985 US6025344A (en) | 1996-06-17 | 1997-05-27 | Certain dioic acid derivatives useful as NAALADase inhibitors |
PCT/US1997/011538 WO1997048399A1 (en) | 1996-06-17 | 1997-06-16 | Certain phosphinyl derivatives useful as naaladase inhibitors |
Publications (2)
Publication Number | Publication Date |
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LV12232A LV12232A (lv) | 1999-03-20 |
LV12232B true LV12232B (en) | 1999-08-20 |
Family
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Family Applications (1)
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LVP-98-278A LV12232B (en) | 1996-06-17 | 1998-12-15 | KNOWLEDGE PHOSPHINILATED DERIVATIVES AS NECESSARY INHIBITORS |
Country Status (15)
Country | Link |
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US (2) | US6025344A (hu) |
EP (1) | EP0957924A4 (hu) |
JP (1) | JP2002514157A (hu) |
KR (1) | KR20000016749A (hu) |
AU (1) | AU726854B2 (hu) |
CA (1) | CA2258589A1 (hu) |
CZ (1) | CZ390098A3 (hu) |
HU (1) | HUP9902636A2 (hu) |
IL (1) | IL127257A0 (hu) |
LV (1) | LV12232B (hu) |
NO (1) | NO985874L (hu) |
NZ (1) | NZ333234A (hu) |
PL (1) | PL330409A1 (hu) |
TR (1) | TR199802637T2 (hu) |
WO (1) | WO1997048399A1 (hu) |
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-
1997
- 1997-05-27 US US08/858,985 patent/US6025344A/en not_active Expired - Fee Related
- 1997-06-16 EP EP97932448A patent/EP0957924A4/en not_active Withdrawn
- 1997-06-16 HU HU9902636A patent/HUP9902636A2/hu unknown
- 1997-06-16 KR KR1019980710356A patent/KR20000016749A/ko not_active Application Discontinuation
- 1997-06-16 CZ CZ983900A patent/CZ390098A3/cs unknown
- 1997-06-16 AU AU35906/97A patent/AU726854B2/en not_active Ceased
- 1997-06-16 JP JP50190298A patent/JP2002514157A/ja active Pending
- 1997-06-16 CA CA002258589A patent/CA2258589A1/en not_active Abandoned
- 1997-06-16 WO PCT/US1997/011538 patent/WO1997048399A1/en not_active Application Discontinuation
- 1997-06-16 TR TR1998/02637T patent/TR199802637T2/xx unknown
- 1997-06-16 NZ NZ333234A patent/NZ333234A/xx not_active IP Right Cessation
- 1997-06-16 IL IL12725797A patent/IL127257A0/xx unknown
- 1997-06-16 PL PL97330409A patent/PL330409A1/xx unknown
-
1998
- 1998-12-15 NO NO985874A patent/NO985874L/no unknown
- 1998-12-15 LV LVP-98-278A patent/LV12232B/en unknown
-
1999
- 1999-12-17 US US09/466,059 patent/US6479471B1/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
IL127257A0 (en) | 1999-09-22 |
US6025344A (en) | 2000-02-15 |
AU726854B2 (en) | 2000-11-23 |
EP0957924A1 (en) | 1999-11-24 |
US6479471B1 (en) | 2002-11-12 |
KR20000016749A (ko) | 2000-03-25 |
LV12232A (lv) | 1999-03-20 |
NO985874D0 (no) | 1998-12-15 |
PL330409A1 (en) | 1999-05-10 |
JP2002514157A (ja) | 2002-05-14 |
CZ390098A3 (cs) | 1999-05-12 |
WO1997048399A1 (en) | 1997-12-24 |
CA2258589A1 (en) | 1997-12-24 |
NO985874L (no) | 1999-02-15 |
HUP9902636A2 (hu) | 2001-04-28 |
TR199802637T2 (xx) | 1999-03-22 |
NZ333234A (en) | 1999-07-29 |
AU3590697A (en) | 1998-01-07 |
EP0957924A4 (en) | 2000-04-12 |
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