CA2291258A1 - Inhibitors of naaladase enzyme activity - Google Patents
Inhibitors of naaladase enzyme activity Download PDFInfo
- Publication number
- CA2291258A1 CA2291258A1 CA002291258A CA2291258A CA2291258A1 CA 2291258 A1 CA2291258 A1 CA 2291258A1 CA 002291258 A CA002291258 A CA 002291258A CA 2291258 A CA2291258 A CA 2291258A CA 2291258 A1 CA2291258 A1 CA 2291258A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- benzylhydroxyphosphinyl
- hydroxyphosphinyl
- pentanedioic
- pentanedioic acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 230000000694 effects Effects 0.000 title abstract description 36
- 102000004190 Enzymes Human genes 0.000 title abstract description 15
- 108090000790 Enzymes Proteins 0.000 title abstract description 15
- 239000003112 inhibitor Substances 0.000 title description 63
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- -1 hydroxyphosphinyl Chemical class 0.000 claims abstract description 52
- 238000000034 method Methods 0.000 claims abstract description 44
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 112
- 206010028980 Neoplasm Diseases 0.000 claims description 83
- 239000002253 acid Substances 0.000 claims description 58
- 239000000203 mixture Substances 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 241001465754 Metazoa Species 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 31
- 201000011510 cancer Diseases 0.000 claims description 31
- 239000003814 drug Substances 0.000 claims description 24
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 9
- 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 8
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 229940088597 hormone Drugs 0.000 claims description 8
- 239000005556 hormone Substances 0.000 claims description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 8
- 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 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 201000005825 prostate adenocarcinoma Diseases 0.000 claims description 7
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- BGFHFJAUZXWNSA-UHFFFAOYSA-N 2-[1-[(2-fluorophenyl)methyl-hydroxyphosphoryl]hexyl]pentanedioic acid Chemical compound CCCCCC(C(CCC(O)=O)C(O)=O)P(O)(=O)CC1=CC=CC=C1F BGFHFJAUZXWNSA-UHFFFAOYSA-N 0.000 claims description 5
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 4
- 208000003174 Brain Neoplasms Diseases 0.000 claims description 4
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 4
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 4
- 206010038389 Renal cancer Diseases 0.000 claims description 4
- 208000024313 Testicular Neoplasms Diseases 0.000 claims description 4
- 206010057644 Testis cancer Diseases 0.000 claims description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 201000010982 kidney cancer Diseases 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- 201000003120 testicular cancer Diseases 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- BGEHMAARUOAFAE-UHFFFAOYSA-N 2-[1-[hydroxy(methyl)phosphoryl]ethyl]pentanedioic acid Chemical compound CP(=O)(O)C(C)C(C(O)=O)CCC(O)=O BGEHMAARUOAFAE-UHFFFAOYSA-N 0.000 claims description 3
- XJGGXAFLPLVIBA-UHFFFAOYSA-N 2-[1-[hydroxy-[(2,3,4,5,6-pentafluorophenyl)methyl]phosphoryl]heptyl]pentanedioic acid Chemical compound CCCCCCC(C(CCC(O)=O)C(O)=O)P(O)(=O)CC1=C(F)C(F)=C(F)C(F)=C1F XJGGXAFLPLVIBA-UHFFFAOYSA-N 0.000 claims description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 208000006468 Adrenal Cortex Neoplasms Diseases 0.000 claims description 3
- 239000004037 angiogenesis inhibitor Substances 0.000 claims description 3
- 125000001475 halogen functional group Chemical group 0.000 claims description 3
- IOYBOEIDZBUIIS-UHFFFAOYSA-N 2-(1-phosphonobut-2-enyl)pentanedioic acid Chemical compound CC=CC(P(O)(O)=O)C(C(O)=O)CCC(O)=O IOYBOEIDZBUIIS-UHFFFAOYSA-N 0.000 claims description 2
- GBWJRXCXCSVTQG-UHFFFAOYSA-N 2-(2-phosphonopent-4-enyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CC(P(O)(O)=O)CC=C GBWJRXCXCSVTQG-UHFFFAOYSA-N 0.000 claims description 2
- XMUWSTAUNIOSEA-UHFFFAOYSA-N 2-[1-[(4-fluorophenyl)methyl-hydroxyphosphoryl]but-3-enyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(CC=C)P(O)(=O)CC1=CC=C(F)C=C1 XMUWSTAUNIOSEA-UHFFFAOYSA-N 0.000 claims description 2
- SXRNCHJELFIWFJ-UHFFFAOYSA-N 2-[1-[benzyl(hydroxy)phosphoryl]butyl]hexanedioic acid Chemical compound OC(=O)CCCC(C(O)=O)C(CCC)P(O)(=O)CC1=CC=CC=C1 SXRNCHJELFIWFJ-UHFFFAOYSA-N 0.000 claims description 2
- XYRCTOBGZMZMGF-UHFFFAOYSA-N 2-[1-[benzyl(hydroxy)phosphoryl]ethyl]nonanedioic acid Chemical compound OC(=O)CCCCCCC(C(O)=O)C(C)P(O)(=O)CC1=CC=CC=C1 XYRCTOBGZMZMGF-UHFFFAOYSA-N 0.000 claims description 2
- QHPFJSJCOMKLJK-UHFFFAOYSA-N 2-[1-[benzyl(hydroxy)phosphoryl]pentyl]heptanedioic acid Chemical compound OC(=O)CCCCC(C(O)=O)C(CCCC)P(O)(=O)CC1=CC=CC=C1 QHPFJSJCOMKLJK-UHFFFAOYSA-N 0.000 claims description 2
- SCBIMYKFHBPTHT-UHFFFAOYSA-N 2-[1-[benzyl(hydroxy)phosphoryl]propyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(CC)P(O)(=O)CC1=CC=CC=C1 SCBIMYKFHBPTHT-UHFFFAOYSA-N 0.000 claims description 2
- LTZUNMJTYGQNBK-UHFFFAOYSA-N 2-[1-[ethyl(hydroxy)phosphoryl]propyl]pentanedioic acid Chemical compound CCP(O)(=O)C(CC)C(C(O)=O)CCC(O)=O LTZUNMJTYGQNBK-UHFFFAOYSA-N 0.000 claims description 2
- NGNKYOADFJJEBR-UHFFFAOYSA-N 2-[1-[hydroxy(1h-indol-2-yl)phosphoryl]pentyl]pentanedioic acid Chemical compound C1=CC=C2NC(P(O)(=O)C(C(CCC(O)=O)C(O)=O)CCCC)=CC2=C1 NGNKYOADFJJEBR-UHFFFAOYSA-N 0.000 claims description 2
- SCSKHTDKPHKLKV-UHFFFAOYSA-N 2-[1-[hydroxy(1h-indol-3-ylmethyl)phosphoryl]but-3-enyl]pentanedioic acid Chemical compound C1=CC=C2C(CP(O)(=O)C(CC=C)C(CCC(=O)O)C(O)=O)=CNC2=C1 SCSKHTDKPHKLKV-UHFFFAOYSA-N 0.000 claims description 2
- LSQDEBGAGNIOKR-UHFFFAOYSA-N 2-[1-[hydroxy(1h-indol-4-ylmethyl)phosphoryl]pentyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(CCCC)P(O)(=O)CC1=CC=CC2=C1C=CN2 LSQDEBGAGNIOKR-UHFFFAOYSA-N 0.000 claims description 2
- ZSQKZNGLZQAADH-UHFFFAOYSA-N 2-[1-[hydroxy(2-naphthalen-1-ylethyl)phosphoryl]butyl]pentanedioic acid Chemical compound C1=CC=C2C(CCP(O)(=O)C(C(CCC(O)=O)C(O)=O)CCC)=CC=CC2=C1 ZSQKZNGLZQAADH-UHFFFAOYSA-N 0.000 claims description 2
- VYXOUSANBDDBNJ-UHFFFAOYSA-N 2-[1-[hydroxy(2-pyridin-3-ylethyl)phosphoryl]hexyl]pentanedioic acid Chemical compound CCCCCC(C(CCC(O)=O)C(O)=O)P(O)(=O)CCC1=CC=CN=C1 VYXOUSANBDDBNJ-UHFFFAOYSA-N 0.000 claims description 2
- CIQVHMVMQXCBOU-UHFFFAOYSA-N 2-[1-[hydroxy(3-phenylprop-2-enyl)phosphoryl]ethyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(C)P(O)(=O)CC=CC1=CC=CC=C1 CIQVHMVMQXCBOU-UHFFFAOYSA-N 0.000 claims description 2
- GSCUVCCAMUHQJP-UHFFFAOYSA-N 2-[1-[hydroxy(3-phenylpropyl)phosphoryl]heptyl]pentanedioic acid Chemical compound CCCCCCC(C(CCC(O)=O)C(O)=O)P(O)(=O)CCCC1=CC=CC=C1 GSCUVCCAMUHQJP-UHFFFAOYSA-N 0.000 claims description 2
- FQMNPUNTNWYELW-UHFFFAOYSA-N 2-[1-[hydroxy(3-phenylpropyl)phosphoryl]propyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(CC)P(O)(=O)CCCC1=CC=CC=C1 FQMNPUNTNWYELW-UHFFFAOYSA-N 0.000 claims description 2
- JBNGGKWBVOJKSF-UHFFFAOYSA-N 2-[1-[hydroxy(4-naphthalen-1-ylbutyl)phosphoryl]heptyl]pentanedioic acid Chemical compound C1=CC=C2C(CCCCP(O)(=O)C(C(CCC(O)=O)C(O)=O)CCCCCC)=CC=CC2=C1 JBNGGKWBVOJKSF-UHFFFAOYSA-N 0.000 claims description 2
- PHGIEYWXFATORR-UHFFFAOYSA-N 2-[1-[hydroxy(methyl)phosphoryl]hexyl]octanedioic acid Chemical compound CCCCCC(P(C)(O)=O)C(C(O)=O)CCCCCC(O)=O PHGIEYWXFATORR-UHFFFAOYSA-N 0.000 claims description 2
- OWJRZHJPEINKLC-UHFFFAOYSA-N 2-[1-[hydroxy(methyl)phosphoryl]propyl]decanedioic acid Chemical compound CCC(P(C)(O)=O)C(C(O)=O)CCCCCCCC(O)=O OWJRZHJPEINKLC-UHFFFAOYSA-N 0.000 claims description 2
- AUASMYFDSORXAL-UHFFFAOYSA-N 2-[1-[hydroxy(phenyl)phosphoryl]heptyl]pentanedioic acid Chemical compound CCCCCCC(C(CCC(O)=O)C(O)=O)P(O)(=O)C1=CC=CC=C1 AUASMYFDSORXAL-UHFFFAOYSA-N 0.000 claims description 2
- GCVWRLGICCBCDF-UHFFFAOYSA-N 2-[1-[hydroxy(propyl)phosphoryl]butyl]pentanedioic acid Chemical compound CCCP(O)(=O)C(CCC)C(CCC(O)=O)C(O)=O GCVWRLGICCBCDF-UHFFFAOYSA-N 0.000 claims description 2
- MEHWELMZYMWSFX-UHFFFAOYSA-N 2-[1-[hydroxy(pyridin-2-yl)phosphoryl]ethyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(C)P(O)(=O)C1=CC=CC=N1 MEHWELMZYMWSFX-UHFFFAOYSA-N 0.000 claims description 2
- HJORJASCMBBEEA-UHFFFAOYSA-N 2-[1-[hydroxy(pyridin-3-yl)phosphoryl]propyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(CC)P(O)(=O)C1=CC=CN=C1 HJORJASCMBBEEA-UHFFFAOYSA-N 0.000 claims description 2
- IWCYKXNOUARVTM-UHFFFAOYSA-N 2-[1-[hydroxy(pyridin-3-ylmethyl)phosphoryl]but-2-enyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(C=CC)P(O)(=O)CC1=CC=CN=C1 IWCYKXNOUARVTM-UHFFFAOYSA-N 0.000 claims description 2
- XUORNQOLKFEWSU-UHFFFAOYSA-N 2-[1-[hydroxy(pyridin-4-ylmethyl)phosphoryl]pentyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(CCCC)P(O)(=O)CC1=CC=NC=C1 XUORNQOLKFEWSU-UHFFFAOYSA-N 0.000 claims description 2
- IXFBBVFABJPSRW-UHFFFAOYSA-N 2-[1-[hydroxy(thiophen-3-yl)phosphoryl]ethyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(C)P(O)(=O)C=1C=CSC=1 IXFBBVFABJPSRW-UHFFFAOYSA-N 0.000 claims description 2
- QKKQOASRUISMLV-UHFFFAOYSA-N 2-[1-[hydroxy(thiophen-3-yl)phosphoryl]propyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(CC)P(O)(=O)C=1C=CSC=1 QKKQOASRUISMLV-UHFFFAOYSA-N 0.000 claims description 2
- FVSLCDSWCYWKRS-UHFFFAOYSA-N 2-[1-[hydroxy(thiophen-3-ylmethyl)phosphoryl]ethyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(C)P(O)(=O)CC=1C=CSC=1 FVSLCDSWCYWKRS-UHFFFAOYSA-N 0.000 claims description 2
- ZFTNRPLNYSUGRJ-UHFFFAOYSA-N 2-[1-[hydroxy-(2,3,4-trimethoxyphenyl)phosphoryl]hexyl]pentanedioic acid Chemical compound CCCCCC(C(CCC(O)=O)C(O)=O)P(O)(=O)C1=CC=C(OC)C(OC)=C1OC ZFTNRPLNYSUGRJ-UHFFFAOYSA-N 0.000 claims description 2
- BUBUQVYYWDVESJ-UHFFFAOYSA-N 2-[1-[hydroxy-[(3-methylphenyl)methyl]phosphoryl]butyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(CCC)P(O)(=O)CC1=CC=CC(C)=C1 BUBUQVYYWDVESJ-UHFFFAOYSA-N 0.000 claims description 2
- MGZOENIFEFYLKT-UHFFFAOYSA-N 2-[1-[hydroxy-[(4-methoxyphenyl)methyl]phosphoryl]pentyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(CCCC)P(O)(=O)CC1=CC=C(OC)C=C1 MGZOENIFEFYLKT-UHFFFAOYSA-N 0.000 claims description 2
- ZCIUJTQADZXCRD-UHFFFAOYSA-N 2-[1-[hydroxy-[(4-methylphenyl)methyl]phosphoryl]but-3-enyl]pentanedioic acid Chemical compound CC1=CC=C(CP(O)(=O)C(CC=C)C(CCC(O)=O)C(O)=O)C=C1 ZCIUJTQADZXCRD-UHFFFAOYSA-N 0.000 claims description 2
- BRMQLMQKNRLEOM-UHFFFAOYSA-N 2-[1-[hydroxy-[(4-methylphenyl)methyl]phosphoryl]butyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(CCC)P(O)(=O)CC1=CC=C(C)C=C1 BRMQLMQKNRLEOM-UHFFFAOYSA-N 0.000 claims description 2
- RFTRVRMCOSTWJG-UHFFFAOYSA-N 2-[1-[hydroxy-[2-(1h-indol-3-yl)ethyl]phosphoryl]hexyl]pentanedioic acid Chemical compound C1=CC=C2C(CCP(O)(=O)C(C(CCC(O)=O)C(O)=O)CCCCC)=CNC2=C1 RFTRVRMCOSTWJG-UHFFFAOYSA-N 0.000 claims description 2
- YMEMUUKZWAQHDE-UHFFFAOYSA-N 2-[1-[hydroxy-[[3-(trifluoromethyl)phenyl]methyl]phosphoryl]ethyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(C)P(O)(=O)CC1=CC=CC(C(F)(F)F)=C1 YMEMUUKZWAQHDE-UHFFFAOYSA-N 0.000 claims description 2
- UTAXKAHWANBGHG-UHFFFAOYSA-N 2-[1-[hydroxy-[hydroxy(phenyl)methyl]phosphoryl]but-2-enyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(C=CC)P(O)(=O)C(O)C1=CC=CC=C1 UTAXKAHWANBGHG-UHFFFAOYSA-N 0.000 claims description 2
- ZESXUVOYSOPBPM-UHFFFAOYSA-N 2-[2-[benzyl(hydroxy)phosphoryl]propyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CC(C)P(O)(=O)CC1=CC=CC=C1 ZESXUVOYSOPBPM-UHFFFAOYSA-N 0.000 claims description 2
- KJEGRPRHSIKXOL-UHFFFAOYSA-N 2-[2-[hydroxy(4-naphthalen-2-ylbutyl)phosphoryl]pentyl]pentanedioic acid Chemical compound C1=CC=CC2=CC(CCCCP(O)(=O)C(CC(CCC(O)=O)C(O)=O)CCC)=CC=C21 KJEGRPRHSIKXOL-UHFFFAOYSA-N 0.000 claims description 2
- MNVMHWCGROANRL-UHFFFAOYSA-N 2-[2-[hydroxy(naphthalen-2-yl)phosphoryl]butyl]pentanedioic acid Chemical compound C1=CC=CC2=CC(P(O)(=O)C(CC(CCC(O)=O)C(O)=O)CC)=CC=C21 MNVMHWCGROANRL-UHFFFAOYSA-N 0.000 claims description 2
- IDZQNAVUYGNJAK-UHFFFAOYSA-N 2-[2-[hydroxy(thiophen-2-yl)phosphoryl]propyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CC(C)P(O)(=O)C1=CC=CS1 IDZQNAVUYGNJAK-UHFFFAOYSA-N 0.000 claims description 2
- LELHEMVPYWANHT-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]-phenylmethyl]pentanedioic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)C(C(CCC(=O)O)C(O)=O)C1=CC=CC=C1 LELHEMVPYWANHT-UHFFFAOYSA-N 0.000 claims description 2
- ZOHUZULHQOYVHB-UHFFFAOYSA-N 2-[[hydroxy(thiophen-2-yl)phosphoryl]-phenylmethyl]pentanedioic acid Chemical compound C=1C=CSC=1P(O)(=O)C(C(CCC(=O)O)C(O)=O)C1=CC=CC=C1 ZOHUZULHQOYVHB-UHFFFAOYSA-N 0.000 claims description 2
- AONMUDVDMNNSIK-UHFFFAOYSA-N 2-[fluoro-[hydroxy(phenyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(F)P(O)(=O)C1=CC=CC=C1 AONMUDVDMNNSIK-UHFFFAOYSA-N 0.000 claims description 2
- FIXQDCFNDMNABV-UHFFFAOYSA-N 2-benzyl-3-[benzyl(hydroxy)phosphoryl]hexanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)C(CCC)C(C(O)=O)CC1=CC=CC=C1 FIXQDCFNDMNABV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- CVKMFSAVYPAZTQ-UHFFFAOYSA-N 2-methylhexanoic acid Chemical compound CCCCC(C)C(O)=O CVKMFSAVYPAZTQ-UHFFFAOYSA-N 0.000 claims description 2
- XWJWKGRZFZAQRJ-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(1h-indol-2-yl)pentanoic acid Chemical compound C=1C2=CC=CC=C2NC=1C(C(O)=O)C(CC)P(O)(=O)CC1=CC=CC=C1 XWJWKGRZFZAQRJ-UHFFFAOYSA-N 0.000 claims description 2
- ITGJZLZOLBICFP-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(1h-indol-2-ylmethyl)nonanoic acid Chemical compound C=1C2=CC=CC=C2NC=1CC(C(O)=O)C(CCCCCC)P(O)(=O)CC1=CC=CC=C1 ITGJZLZOLBICFP-UHFFFAOYSA-N 0.000 claims description 2
- VXQNXNJOTLGRCN-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(1h-indol-3-yl)-2-methyl-3-propylnonanoic acid Chemical compound C=1NC2=CC=CC=C2C=1C(C)(C(O)=O)C(CCC)(CCCCCC)P(O)(=O)CC1=CC=CC=C1 VXQNXNJOTLGRCN-UHFFFAOYSA-N 0.000 claims description 2
- DRUABVFBUJXGBN-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(1h-indol-3-yl)hexanoic acid Chemical compound C=1NC2=CC=CC=C2C=1C(C(O)=O)C(CCC)P(O)(=O)CC1=CC=CC=C1 DRUABVFBUJXGBN-UHFFFAOYSA-N 0.000 claims description 2
- RXHPEQFCYXJZKV-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(1h-indol-4-ylmethyl)butanoic acid Chemical compound C=1C=CC=2NC=CC=2C=1CC(C(O)=O)C(C)P(O)(=O)CC1=CC=CC=C1 RXHPEQFCYXJZKV-UHFFFAOYSA-N 0.000 claims description 2
- OFJATMQASSTFRI-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(2,3,4-trimethoxyphenyl)nonanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)C(CCCCCC)C(C(O)=O)C1=CC=C(OC)C(OC)=C1OC OFJATMQASSTFRI-UHFFFAOYSA-N 0.000 claims description 2
- MDDYOLBBAKMWBD-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(2-phenylethyl)hex-4-enoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)C(C=CC)C(C(O)=O)CCC1=CC=CC=C1 MDDYOLBBAKMWBD-UHFFFAOYSA-N 0.000 claims description 2
- UXFRIBJXJAROTC-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(2-pyridin-3-ylethyl)pentanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)C(CC)C(C(O)=O)CCC1=CC=CN=C1 UXFRIBJXJAROTC-UHFFFAOYSA-N 0.000 claims description 2
- NEOZBTNTIZMOON-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(cyclohexylmethyl)butanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)C(C)C(C(O)=O)CC1CCCCC1 NEOZBTNTIZMOON-UHFFFAOYSA-N 0.000 claims description 2
- GWXIIRKGBNUFBL-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(naphthalen-1-ylmethyl)pentanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1CC(C(O)=O)C(CC)P(O)(=O)CC1=CC=CC=C1 GWXIIRKGBNUFBL-UHFFFAOYSA-N 0.000 claims description 2
- NABYMBZOJLMPCD-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(oxolan-2-yl)butanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)C(C)C(C(O)=O)C1CCCO1 NABYMBZOJLMPCD-UHFFFAOYSA-N 0.000 claims description 2
- FSUTWVDKCRCXKN-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(pyridin-2-ylmethyl)nonanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)C(CCCCCC)C(C(O)=O)CC1=CC=CC=N1 FSUTWVDKCRCXKN-UHFFFAOYSA-N 0.000 claims description 2
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-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/06—Tripeptides
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- 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
- C07F9/30—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
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- 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
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- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/863,624 US6046180A (en) | 1996-06-17 | 1997-05-27 | NAALADase inhibitors |
US08/858,985 US6025344A (en) | 1996-06-17 | 1997-05-27 | Certain dioic acid derivatives useful as NAALADase inhibitors |
US08/858,985 | 1997-05-27 | ||
US08/864,545 | 1997-05-28 | ||
US08/864,545 US6011021A (en) | 1996-06-17 | 1997-05-28 | Methods of cancer treatment using naaladase inhibitors |
US08/863,624 | 1997-06-27 | ||
US08/900,194 US6025345A (en) | 1996-06-17 | 1997-07-25 | Inhibitors of NAALADase enzyme activity |
US08/900,194 | 1997-07-25 | ||
PCT/US1997/014347 WO1998053812A1 (en) | 1997-05-27 | 1997-08-15 | Inhibitors of naaladase enzyme activity |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2291258A1 true CA2291258A1 (en) | 1998-12-03 |
Family
ID=27505934
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002291258A Abandoned CA2291258A1 (en) | 1997-05-27 | 1997-08-15 | Inhibitors of naaladase enzyme activity |
Country Status (4)
Country | Link |
---|---|
JP (1) | JP2002514158A (ja) |
AU (1) | AU739443B2 (ja) |
CA (1) | CA2291258A1 (ja) |
ID (1) | ID20347A (ja) |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6046180A (en) * | 1996-06-17 | 2000-04-04 | Guilford Pharmaceuticals Inc. | NAALADase inhibitors |
ID18382A (id) * | 1996-09-27 | 1998-04-02 | Guilford Pharm Inc | Komposisi sediaan farmasi dan metoda pengobatan gangguan kompulsif dengan menggunakan inhibitor naaladase |
TR199901173T2 (xx) * | 1996-09-27 | 1999-07-21 | Guilford Pharmaceuticals, Inc. | Canl�larda glutamat anormalli�inin tedavisi ve n�ronal aktivitenin d�zenlenmesi i�in y�ntemler ve NAALADase bile�imleri. |
-
1997
- 1997-08-11 ID IDP972781A patent/ID20347A/id unknown
- 1997-08-15 JP JP50191298A patent/JP2002514158A/ja active Pending
- 1997-08-15 CA CA002291258A patent/CA2291258A1/en not_active Abandoned
- 1997-08-15 AU AU39821/97A patent/AU739443B2/en not_active Ceased
Also Published As
Publication number | Publication date |
---|---|
AU3982197A (en) | 1998-12-30 |
JP2002514158A (ja) | 2002-05-14 |
AU739443B2 (en) | 2001-10-11 |
ID20347A (id) | 1998-12-03 |
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Legal Events
Date | Code | Title | Description |
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EEER | Examination request | ||
FZDE | Dead |