LV12253B - Naaladāzes inhibitori un to pielietojums vēža ārstēšanai - Google Patents
Naaladāzes inhibitori un to pielietojums vēža ārstēšanai Download PDFInfo
- Publication number
- LV12253B LV12253B LVP-98-279A LV980279A LV12253B LV 12253 B LV12253 B LV 12253B LV 980279 A LV980279 A LV 980279A LV 12253 B LV12253 B LV 12253B
- Authority
- LV
- Latvia
- Prior art keywords
- acid
- oxy
- amino
- benzyloxyphosphinyl
- pentanedioic
- Prior art date
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- 239000003112 inhibitor Substances 0.000 title claims description 141
- 206010028980 Neoplasm Diseases 0.000 title claims description 120
- 201000011510 cancer Diseases 0.000 title claims description 51
- -1 hydroxyphosphinyl Chemical class 0.000 claims abstract description 774
- 150000001875 compounds Chemical class 0.000 claims abstract description 145
- 238000000034 method Methods 0.000 claims abstract description 48
- 206010060862 Prostate cancer Diseases 0.000 claims abstract description 43
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 40
- 230000000694 effects Effects 0.000 claims abstract description 39
- 208000017497 prostate disease Diseases 0.000 claims abstract description 13
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 313
- 108090000369 Glutamate Carboxypeptidase II Proteins 0.000 claims description 167
- 239000000203 mixture Substances 0.000 claims description 142
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 122
- 238000011282 treatment Methods 0.000 claims description 88
- 239000002253 acid Substances 0.000 claims description 85
- 125000003342 alkenyl group Chemical group 0.000 claims description 77
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 69
- 150000003839 salts Chemical class 0.000 claims description 68
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 63
- 210000004027 cell Anatomy 0.000 claims description 42
- ISEYJGQFXSTPMQ-UHFFFAOYSA-N 2-(phosphonomethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(O)=O ISEYJGQFXSTPMQ-UHFFFAOYSA-N 0.000 claims description 39
- 125000000753 cycloalkyl group Chemical class 0.000 claims description 39
- 125000001931 aliphatic group Chemical group 0.000 claims description 38
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 37
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 36
- 125000003118 aryl group Chemical class 0.000 claims description 35
- 125000002837 carbocyclic group Chemical group 0.000 claims description 35
- 239000000126 substance Substances 0.000 claims description 35
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 33
- 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 28
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 28
- 239000003814 drug Substances 0.000 claims description 28
- 241001465754 Metazoa Species 0.000 claims description 27
- 239000001257 hydrogen Substances 0.000 claims description 25
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 238000002347 injection Methods 0.000 claims description 23
- 239000007924 injection Substances 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 21
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
- 239000001301 oxygen Substances 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 20
- LGBHWCHYODMSKL-UHFFFAOYSA-N 2-[[(2-fluorophenyl)methyl-hydroxyphosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC1=CC=CC=C1F LGBHWCHYODMSKL-UHFFFAOYSA-N 0.000 claims description 17
- 230000002401 inhibitory effect Effects 0.000 claims description 17
- 229940088597 hormone Drugs 0.000 claims description 16
- 239000005556 hormone Substances 0.000 claims description 16
- CYVJVQLEPWFFCF-UHFFFAOYSA-N 2-[(2-fluorophenyl)methyl-hydroxyphosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1=CC=CC=C1F CYVJVQLEPWFFCF-UHFFFAOYSA-N 0.000 claims description 15
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 15
- 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 14
- KKGSCLRYTMKKLP-UHFFFAOYSA-N 2-(phosphonoamino)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(O)=O KKGSCLRYTMKKLP-UHFFFAOYSA-N 0.000 claims description 14
- 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 14
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
- HCNFYUWPTGVLOQ-UHFFFAOYSA-N 3-[hydroxy(thiophen-3-yl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)C=1C=CSC=1 HCNFYUWPTGVLOQ-UHFFFAOYSA-N 0.000 claims description 14
- 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 13
- RWTNGNACMXDVQP-UHFFFAOYSA-N 2-[[hydroxy(thiophen-3-ylmethyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC=1C=CSC=1 RWTNGNACMXDVQP-UHFFFAOYSA-N 0.000 claims description 13
- 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 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
- DKFCZKUFXCMIAP-UHFFFAOYSA-N 2-[[(2-fluorophenyl)methyl-hydroxyphosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1=CC=CC=C1F DKFCZKUFXCMIAP-UHFFFAOYSA-N 0.000 claims description 12
- XPTOUPHGGSTLHI-UHFFFAOYSA-N 2-[[(4-fluorophenyl)-hydroxyphosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)C1=CC=C(F)C=C1 XPTOUPHGGSTLHI-UHFFFAOYSA-N 0.000 claims description 12
- POLVGRCQKICNOH-UHFFFAOYSA-N 2-[[(4-fluorophenyl)methyl-hydroxyphosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1=CC=C(F)C=C1 POLVGRCQKICNOH-UHFFFAOYSA-N 0.000 claims description 12
- OYVOQEGFXVKTIL-UHFFFAOYSA-N 2-[[(4-fluorophenyl)methyl-hydroxyphosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC1=CC=C(F)C=C1 OYVOQEGFXVKTIL-UHFFFAOYSA-N 0.000 claims description 12
- LEXGADWOXKHTNB-UHFFFAOYSA-N 2-[[hydroxy(thiophen-3-yl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)C=1C=CSC=1 LEXGADWOXKHTNB-UHFFFAOYSA-N 0.000 claims description 12
- MBPGRTVAJROGND-UHFFFAOYSA-N 2-[[hydroxy(thiophen-3-yl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)C=1C=CSC=1 MBPGRTVAJROGND-UHFFFAOYSA-N 0.000 claims description 12
- 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 12
- DEFHYMRFBAYION-UHFFFAOYSA-N 2-[[hydroxy(thiophen-3-ylmethyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CC=1C=CSC=1 DEFHYMRFBAYION-UHFFFAOYSA-N 0.000 claims description 12
- KWUQXTWAEHRRNT-UHFFFAOYSA-N 2-[[hydroxy-[(3-methylphenyl)methyl]phosphoryl]methyl]pentanedioic acid Chemical compound CC1=CC=CC(CP(O)(=O)CC(CCC(O)=O)C(O)=O)=C1 KWUQXTWAEHRRNT-UHFFFAOYSA-N 0.000 claims description 12
- 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 12
- YZGBWFOXCWDWSP-UHFFFAOYSA-N 2-[hydroxy(thiophen-3-yl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)C=1C=CSC=1 YZGBWFOXCWDWSP-UHFFFAOYSA-N 0.000 claims description 12
- JJKOBUUDRGAVEK-UHFFFAOYSA-N 2-[hydroxy-[[3-(trifluoromethyl)phenyl]methyl]phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1=CC=CC(C(F)(F)F)=C1 JJKOBUUDRGAVEK-UHFFFAOYSA-N 0.000 claims description 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
- 201000005825 prostate adenocarcinoma Diseases 0.000 claims description 12
- IDPMTZKPKDZJNV-UHFFFAOYSA-N 2-[(4-fluorophenyl)methyl-hydroxyphosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1=CC=C(F)C=C1 IDPMTZKPKDZJNV-UHFFFAOYSA-N 0.000 claims description 11
- JCNLQFPTNJDDBA-UHFFFAOYSA-N 2-[[(4-fluorophenyl)-hydroxyphosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C1=CC=C(F)C=C1 JCNLQFPTNJDDBA-UHFFFAOYSA-N 0.000 claims description 11
- DOFBJKROBHLNQF-UHFFFAOYSA-N 2-[[hydroxy-[(2,3,4,5,6-pentafluorophenyl)methyl]phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1=C(F)C(F)=C(F)C(F)=C1F DOFBJKROBHLNQF-UHFFFAOYSA-N 0.000 claims description 11
- PEUZLKMPHXDVCI-UHFFFAOYSA-N 2-[[hydroxy-[(3-methylphenyl)methyl]phosphoryl]amino]pentanedioic acid Chemical compound CC1=CC=CC(CP(O)(=O)NC(CCC(O)=O)C(O)=O)=C1 PEUZLKMPHXDVCI-UHFFFAOYSA-N 0.000 claims description 11
- SWBDJEOHCFZCCJ-UHFFFAOYSA-N 2-[[hydroxy-[(4-methylphenyl)methyl]phosphoryl]amino]pentanedioic acid Chemical compound CC1=CC=C(CP(O)(=O)NC(CCC(O)=O)C(O)=O)C=C1 SWBDJEOHCFZCCJ-UHFFFAOYSA-N 0.000 claims description 11
- ARSRTTFMMOQPTN-UHFFFAOYSA-N 2-[[hydroxy-[(4-methylphenyl)methyl]phosphoryl]methyl]pentanedioic acid Chemical compound CC1=CC=C(CP(O)(=O)CC(CCC(O)=O)C(O)=O)C=C1 ARSRTTFMMOQPTN-UHFFFAOYSA-N 0.000 claims description 11
- FNMLFPXOJJFXCA-UHFFFAOYSA-N 2-[[hydroxy-[[3-(trifluoromethyl)phenyl]methyl]phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC1=CC=CC(C(F)(F)F)=C1 FNMLFPXOJJFXCA-UHFFFAOYSA-N 0.000 claims description 11
- BQMIDMUGWWSPMB-UHFFFAOYSA-N 2-[hydroxy(thiophen-3-ylmethyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CC=1C=CSC=1 BQMIDMUGWWSPMB-UHFFFAOYSA-N 0.000 claims description 11
- RCESSRYCLKVLRD-UHFFFAOYSA-N 2-[hydroxy-[(3-methylphenyl)methyl]phosphoryl]oxypentanedioic acid Chemical compound CC1=CC=CC(CP(O)(=O)OC(CCC(O)=O)C(O)=O)=C1 RCESSRYCLKVLRD-UHFFFAOYSA-N 0.000 claims description 11
- MZGBIOWKDIUFFG-UHFFFAOYSA-N 2-phosphonooxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(O)=O MZGBIOWKDIUFFG-UHFFFAOYSA-N 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- XAZZWLYWTWPPNL-UHFFFAOYSA-N 2-[(4-fluorophenyl)-hydroxyphosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)C1=CC=C(F)C=C1 XAZZWLYWTWPPNL-UHFFFAOYSA-N 0.000 claims description 10
- WSHKRHNRJNQHLM-UHFFFAOYSA-N 2-[[hydroxy(2-phenylethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CCC1=CC=CC=C1 WSHKRHNRJNQHLM-UHFFFAOYSA-N 0.000 claims description 10
- YECLUONKYCPSNK-UHFFFAOYSA-N 2-[[hydroxy-[[3-(trifluoromethyl)phenyl]methyl]phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1=CC=CC(C(F)(F)F)=C1 YECLUONKYCPSNK-UHFFFAOYSA-N 0.000 claims description 10
- KQSJGWUTRARGLX-UHFFFAOYSA-N 2-[hydroxy(thiophen-3-yl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)C=1C=CSC=1 KQSJGWUTRARGLX-UHFFFAOYSA-N 0.000 claims description 10
- PKAHXOUYUIICIV-UHFFFAOYSA-N 3-[hydroxy(thiophen-3-ylmethyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CC=1C=CSC=1 PKAHXOUYUIICIV-UHFFFAOYSA-N 0.000 claims description 10
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
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- 150000002306 glutamic acid derivatives Chemical class 0.000 claims description 10
- 229920000642 polymer Polymers 0.000 claims description 10
- 201000003120 testicular cancer Diseases 0.000 claims description 10
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- 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 9
- SVAHMQCUSNJPRX-UHFFFAOYSA-N 2-[[hydroxy-[(2,3,4,5,6-pentafluorophenyl)methyl]phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC1=C(F)C(F)=C(F)C(F)=C1F SVAHMQCUSNJPRX-UHFFFAOYSA-N 0.000 claims description 9
- MZTCYOOMRRHYLS-UHFFFAOYSA-N 2-[hydroxy-[(2,3,4,5,6-pentafluorophenyl)methyl]phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1=C(F)C(F)=C(F)C(F)=C1F MZTCYOOMRRHYLS-UHFFFAOYSA-N 0.000 claims description 9
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 9
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 9
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 9
- 201000005202 lung cancer Diseases 0.000 claims description 9
- 208000020816 lung neoplasm Diseases 0.000 claims description 9
- 230000001225 therapeutic effect Effects 0.000 claims description 9
- 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 8
- XXWXITBUQFYWJL-UHFFFAOYSA-N 2-[hydroxy(methyl)phosphoryl]oxyhexanedioic acid Chemical compound CP(O)(=O)OC(C(O)=O)CCCC(O)=O XXWXITBUQFYWJL-UHFFFAOYSA-N 0.000 claims description 8
- JEYKSCFWVYRLMS-UHFFFAOYSA-N 2-[hydroxy(naphthalen-2-yl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1P(O)(=O)OC(C(=O)O)C1=CC=CC=C1 JEYKSCFWVYRLMS-UHFFFAOYSA-N 0.000 claims description 8
- VFRDKQXHIWLNCO-UHFFFAOYSA-N 2-[hydroxy-[(4-methylphenyl)methyl]phosphoryl]oxypentanedioic acid Chemical compound CC1=CC=C(CP(O)(=O)OC(CCC(O)=O)C(O)=O)C=C1 VFRDKQXHIWLNCO-UHFFFAOYSA-N 0.000 claims description 8
- RTYBLIQDONZPNL-UHFFFAOYSA-N 3-[hydroxy(2-naphthalen-2-ylethyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1CCP(O)(=O)CC(C(=O)O)C1=CC=CC=C1 RTYBLIQDONZPNL-UHFFFAOYSA-N 0.000 claims description 8
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 8
- 206010033128 Ovarian cancer Diseases 0.000 claims description 8
- 206010061535 Ovarian neoplasm Diseases 0.000 claims description 8
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- 206010039491 Sarcoma Diseases 0.000 claims description 8
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- 229940124597 therapeutic agent Drugs 0.000 claims description 8
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- ROSYJHOMEFISAK-UHFFFAOYSA-N 2-[[ethyl(hydroxy)phosphoryl]amino]pentanedioic acid Chemical compound CCP(O)(=O)NC(C(O)=O)CCC(O)=O ROSYJHOMEFISAK-UHFFFAOYSA-N 0.000 claims description 7
- LZPVIXHUAAWJOK-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-3-yl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1NC2=CC=CC=C2C=1P(O)(=O)NC(C(=O)O)C1=CC=CC=C1 LZPVIXHUAAWJOK-UHFFFAOYSA-N 0.000 claims description 7
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- NPVGHZOJXNTGBD-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]amino]nonanedioic acid Chemical compound CP(O)(=O)NC(C(O)=O)CCCCCCC(O)=O NPVGHZOJXNTGBD-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- IHMUNYQWPXGHMI-UHFFFAOYSA-N 2-[[hydroxy(naphthalen-1-yl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=C2C(P(O)(=O)CC(CCC(=O)O)C(O)=O)=CC=CC2=C1 IHMUNYQWPXGHMI-UHFFFAOYSA-N 0.000 claims description 7
- GKHDJEWVCLDLKH-UHFFFAOYSA-N 2-[[hydroxy(naphthalen-1-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2C(CP(O)(=O)NC(CCC(=O)O)C(O)=O)=CC=CC2=C1 GKHDJEWVCLDLKH-UHFFFAOYSA-N 0.000 claims description 7
- WTEDQNTZBJLCHS-UHFFFAOYSA-N 2-[[hydroxy(naphthalen-2-yl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=CC2=CC(P(O)(=O)NC(CCC(=O)O)C(O)=O)=CC=C21 WTEDQNTZBJLCHS-UHFFFAOYSA-N 0.000 claims description 7
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- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
-
- 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)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
-
- 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)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3826—Acyclic unsaturated acids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/665,775 US5804602A (en) | 1996-06-17 | 1996-06-17 | Methods of cancer treatment using naaladase inhibitors |
US08/864,545 US6011021A (en) | 1996-06-17 | 1997-05-28 | Methods of cancer treatment using naaladase inhibitors |
PCT/US1997/010149 WO1997048409A1 (en) | 1996-06-17 | 1997-06-13 | Methods of cancer treatment using naaladase inhibitors |
ZA977087A ZA977087B (en) | 1996-06-17 | 1997-08-08 | Methods of cancer treatment using naaladase inhibitors |
Publications (2)
Publication Number | Publication Date |
---|---|
LV12253A LV12253A (lv) | 1999-04-20 |
LV12253B true LV12253B (lv) | 2000-01-20 |
Family
ID=27418138
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
LVP-98-279A LV12253B (lv) | 1996-06-17 | 1999-02-11 | Naaladāzes inhibitori un to pielietojums vēža ārstēšanai |
Country Status (10)
Country | Link |
---|---|
US (1) | US6011021A (xx) |
EP (1) | EP0954295A1 (xx) |
CN (1) | CN1221346A (xx) |
BR (1) | BR9709819A (xx) |
CA (1) | CA2257433A1 (xx) |
LV (1) | LV12253B (xx) |
NO (1) | NO985652L (xx) |
PL (1) | PL330782A1 (xx) |
WO (1) | WO1997048409A1 (xx) |
ZA (1) | ZA977087B (xx) |
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US6953668B1 (en) | 1992-11-05 | 2005-10-11 | Sloan-Kettering Institute For Cancer Research | Prostate-specific membrane antigen |
US6569432B1 (en) * | 1995-02-24 | 2003-05-27 | Sloan-Kettering Institute For Cancer Research | Prostate-specific membrane antigen and uses thereof |
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DE69635801T2 (de) | 1995-02-24 | 2006-11-02 | Sloan-Kettering Institute For Cancer Research | Prostataspezifisches membranes antigen und seine anwendungen |
US20040253246A1 (en) * | 1996-02-23 | 2004-12-16 | Israeli Ron S. | Prostate-specific membrane antigen and uses thereof |
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-
1997
- 1997-05-28 US US08/864,545 patent/US6011021A/en not_active Expired - Fee Related
- 1997-06-13 CA CA002257433A patent/CA2257433A1/en not_active Abandoned
- 1997-06-13 EP EP97929944A patent/EP0954295A1/en not_active Withdrawn
- 1997-06-13 CN CN97195439A patent/CN1221346A/zh active Pending
- 1997-06-13 BR BR9709819-1A patent/BR9709819A/pt not_active IP Right Cessation
- 1997-06-13 PL PL97330782A patent/PL330782A1/xx unknown
- 1997-06-13 WO PCT/US1997/010149 patent/WO1997048409A1/en not_active Application Discontinuation
- 1997-08-08 ZA ZA977087A patent/ZA977087B/xx unknown
-
1998
- 1998-12-03 NO NO985652A patent/NO985652L/no not_active Application Discontinuation
-
1999
- 1999-02-11 LV LVP-98-279A patent/LV12253B/lv unknown
Also Published As
Publication number | Publication date |
---|---|
ZA977087B (en) | 1999-06-30 |
US6011021A (en) | 2000-01-04 |
NO985652D0 (no) | 1998-12-03 |
CA2257433A1 (en) | 1997-12-04 |
CN1221346A (zh) | 1999-06-30 |
NO985652L (no) | 1999-02-09 |
LV12253A (lv) | 1999-04-20 |
WO1997048409A1 (en) | 1997-12-24 |
BR9709819A (pt) | 2000-01-11 |
EP0954295A1 (en) | 1999-11-10 |
PL330782A1 (en) | 1999-06-07 |
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