AU739443B2 - Inhibitors of naaladase enzyme activity - Google Patents

Inhibitors of naaladase enzyme activity Download PDF

Info

Publication number: AU739443B2
Authority: AU; Australia
Prior art keywords: acid; benzylhydroxyphosphinyl; pentanedioic; hydroxyphosphinyl; propanoic acid
Prior art date: 1997-05-27
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.): Ceased

Application number

AU39821/97A

Other languages

English (en)

Other versions

AU3982197A (en

Inventor

Paul F. Jackson

Keith M. Maclin

Barbara S. Slusher

Kevin L. Tays

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eisai Corp of North America

Original Assignee

Guilford Pharmaceuticals Inc

Priority date (The priority date 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 date listed.)

1997-05-27

Filing date

1997-08-15

Publication date

2001-10-11

1997-05-27 Priority claimed from US08/863,624 external-priority patent/US6046180A/en

1997-05-27 Priority claimed from US08/858,985 external-priority patent/US6025344A/en

1997-05-28 Priority claimed from US08/864,545 external-priority patent/US6011021A/en

1997-07-25 Priority claimed from US08/900,194 external-priority patent/US6025345A/en

1997-08-15 Application filed by Guilford Pharmaceuticals Inc filed Critical Guilford Pharmaceuticals Inc

1997-08-15 Priority claimed from PCT/US1997/014347 external-priority patent/WO1998053812A1/en

1998-12-30 Publication of AU3982197A publication Critical patent/AU3982197A/en

2001-10-11 Application granted granted Critical

2001-10-11 Publication of AU739443B2 publication Critical patent/AU739443B2/en

2017-08-15 Anticipated expiration legal-status Critical

Status Ceased legal-status Critical Current

Links

239000003112 inhibitor Substances 0.000 title description 62
230000000694 effects Effects 0.000 title description 38
102000004190 Enzymes Human genes 0.000 title description 10
108090000790 Enzymes Proteins 0.000 title description 10
239000002253 acid Substances 0.000 claims description 199
JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 184
-1 Cs-C Chemical group 0.000 claims description 149
150000001875 compounds Chemical class 0.000 claims description 110
206010028980 Neoplasm Diseases 0.000 claims description 78
238000000034 method Methods 0.000 claims description 44
239000000203 mixture Substances 0.000 claims description 42
125000000217 alkyl group Chemical group 0.000 claims description 36
125000003342 alkenyl group Chemical group 0.000 claims description 35
241001465754 Metazoa Species 0.000 claims description 31
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
201000011510 cancer Diseases 0.000 claims description 27
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 26
235000019260 propionic acid Nutrition 0.000 claims description 26
239000003814 drug Substances 0.000 claims description 24
DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 claims description 24
125000000753 cycloalkyl group Chemical group 0.000 claims description 22
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 21
239000001257 hydrogen Substances 0.000 claims description 20
125000000896 monocarboxylic acid group Chemical group 0.000 claims description 20
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 18
125000000392 cycloalkenyl group Chemical group 0.000 claims description 18
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 17
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 16
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 15
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 14
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 14
150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 13
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 13
125000003118 aryl group Chemical group 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 11
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 10
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
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
229940088597 hormone Drugs 0.000 claims description 8
239000005556 hormone Substances 0.000 claims description 8
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 7
125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
201000005825 prostate adenocarcinoma Diseases 0.000 claims description 7
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 claims description 6
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 claims description 6
229910052736 halogen Inorganic materials 0.000 claims description 6
150000002367 halogens Chemical class 0.000 claims description 6
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims description 6
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 claims description 5
229940124597 therapeutic agent Drugs 0.000 claims description 5
230000001225 therapeutic effect Effects 0.000 claims description 5
206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 4
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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
239000003937 drug carrier Substances 0.000 claims description 4
125000001475 halogen functional group Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 4
201000010982 kidney cancer Diseases 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 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
CVKMFSAVYPAZTQ-UHFFFAOYSA-N 2-methylhexanoic acid Chemical compound CCCCC(C)C(O)=O CVKMFSAVYPAZTQ-UHFFFAOYSA-N 0.000 claims description 3
125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims description 3
208000006468 Adrenal Cortex Neoplasms Diseases 0.000 claims description 3
229920000305 Nylon 6,10 Polymers 0.000 claims description 3
125000003302 alkenyloxy group Chemical group 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
239000004037 angiogenesis inhibitor Substances 0.000 claims description 3
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
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
SFXXYKYOGGWUHX-UHFFFAOYSA-N 2-phenylpentanoic acid Chemical compound CCCC(C(O)=O)C1=CC=CC=C1 SFXXYKYOGGWUHX-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
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
GNKUTIXMWUSVNZ-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-methylhex-5-enoic acid Chemical compound OC(=O)C(C)C(CC=C)P(O)(=O)CC1=CC=CC=C1 GNKUTIXMWUSVNZ-UHFFFAOYSA-N 0.000 claims description 2
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
GYTUBYBAFVSSNE-UHFFFAOYSA-N 5-[benzyl(hydroxy)phosphoryl]-2-methyl-4-pyridin-3-yloctanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)C(CCC)C(CC(C)C(O)=O)C1=CC=CN=C1 GYTUBYBAFVSSNE-UHFFFAOYSA-N 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 2
125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims 2
WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 claims 2
230000000973 chemotherapeutic effect Effects 0.000 claims 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
UBVFWLHAMDUGCM-UHFFFAOYSA-N 2-(1h-indol-3-yl)-2-methylbutanoic acid Chemical compound C1=CC=C2C(C(C)(C(O)=O)CC)=CNC2=C1 UBVFWLHAMDUGCM-UHFFFAOYSA-N 0.000 claims 1
NRNNGLSVDWFILP-UHFFFAOYSA-N 2-[1-[benzyl(hydroxy)phosphoryl]butyl]decanedioic acid Chemical compound OC(=O)CCCCCCCC(C(O)=O)C(CCC)P(O)(=O)CC1=CC=CC=C1 NRNNGLSVDWFILP-UHFFFAOYSA-N 0.000 claims 1
IBRZZPYVALISRO-UHFFFAOYSA-N 2-[1-[cyclohexyl(hydroxy)phosphoryl]pentyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C(CCCC)P(O)(=O)C1CCCCC1 IBRZZPYVALISRO-UHFFFAOYSA-N 0.000 claims 1
QBJSXFLRGWPVTB-UHFFFAOYSA-N 2-[1-[hydroxy(1h-indol-3-yl)phosphoryl]hexyl]pentanedioic acid Chemical compound C1=CC=C2C(P(O)(=O)C(C(CCC(O)=O)C(O)=O)CCCCC)=CNC2=C1 QBJSXFLRGWPVTB-UHFFFAOYSA-N 0.000 claims 1
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 1
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 1
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 1
125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims 1
GCOOBWJNMRZHBR-UHFFFAOYSA-N 2-methyl-2-naphthalen-1-ylpropanoic acid Chemical compound C1=CC=C2C(C(C)(C(O)=O)C)=CC=CC2=C1 GCOOBWJNMRZHBR-UHFFFAOYSA-N 0.000 claims 1
OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 claims 1
COYMEIBAQDZJCT-UHFFFAOYSA-N 2-phenylnonanoic acid Chemical compound CCCCCCCC(C(O)=O)C1=CC=CC=C1 COYMEIBAQDZJCT-UHFFFAOYSA-N 0.000 claims 1
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 1
ULVBEPJZPQZFEX-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(1h-indol-4-yl)hex-4-enoic acid Chemical compound C=1C=CC=2NC=CC=2C=1C(C(O)=O)C(C=CC)P(O)(=O)CC1=CC=CC=C1 ULVBEPJZPQZFEX-UHFFFAOYSA-N 0.000 claims 1
RQARZNPFZGTQBR-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(2-naphthalen-1-ylethyl)hex-5-enoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1CCC(C(=O)O)C(CC=C)P(O)(=O)CC1=CC=CC=C1 RQARZNPFZGTQBR-UHFFFAOYSA-N 0.000 claims 1
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 1
TWUSLHVAVMZWIB-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-methyl-2-pyridin-2-ylnonanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)C(CCCCCC)C(C)(C(O)=O)C1=CC=CC=N1 TWUSLHVAVMZWIB-UHFFFAOYSA-N 0.000 claims 1
FGSSHUAVLGUSLW-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-methyl-2-pyridin-4-ylbutanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)C(C)C(C)(C(O)=O)C1=CC=NC=C1 FGSSHUAVLGUSLW-UHFFFAOYSA-N 0.000 claims 1
BQKPEXCHNVUSLA-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-methyl-2-thiophen-2-ylhex-4-enoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)C(C=CC)C(C)(C(O)=O)C1=CC=CS1 BQKPEXCHNVUSLA-UHFFFAOYSA-N 0.000 claims 1
YKGYXBAYPXFVCF-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-methyl-3-phenyl-2-pyridin-3-ylpropanoic acid Chemical compound C=1C=CN=CC=1C(C)(C(O)=O)C(P(O)(=O)CC=1C=CC=CC=1)C1=CC=CC=C1 YKGYXBAYPXFVCF-UHFFFAOYSA-N 0.000 claims 1
YYHODDBMQSKTJX-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-phenylbutanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)C(C)C(C(O)=O)C1=CC=CC=C1 YYHODDBMQSKTJX-UHFFFAOYSA-N 0.000 claims 1
GCKFMXPBRZXHBK-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-pyridin-3-ylnonanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)C(CCCCCC)C(C(O)=O)C1=CC=CN=C1 GCKFMXPBRZXHBK-UHFFFAOYSA-N 0.000 claims 1
MFADRBITJVKBKS-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-thiophen-3-ylnonanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)C(CCCCCC)C(C(O)=O)C=1C=CSC=1 MFADRBITJVKBKS-UHFFFAOYSA-N 0.000 claims 1
WIWPWSDEKFCCTN-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-thiophen-3-yloctanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)C(CCCCC)C(C(O)=O)C=1C=CSC=1 WIWPWSDEKFCCTN-UHFFFAOYSA-N 0.000 claims 1
PVROPAZOPQOQDA-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-3-fluoro-2-methyl-2-pyridin-2-ylpropanoic acid Chemical compound C=1C=CC=NC=1C(C)(C(O)=O)C(F)P(O)(=O)CC1=CC=CC=C1 PVROPAZOPQOQDA-UHFFFAOYSA-N 0.000 claims 1
NEDRKMCXQUEVSJ-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-4,4-dimethyl-2-[2-(oxolan-2-yl)ethyl]pentanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)C(C(C)(C)C)C(C(O)=O)CCC1CCCO1 NEDRKMCXQUEVSJ-UHFFFAOYSA-N 0.000 claims 1
LFKJZRXXMYUHMT-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-4,4-dimethyl-2-thiophen-2-ylpentanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)C(C(C)(C)C)C(C(O)=O)C1=CC=CS1 LFKJZRXXMYUHMT-UHFFFAOYSA-N 0.000 claims 1
CNAXODRNDBZOEK-UHFFFAOYSA-N 3-[hydroxy(pyridin-2-yl)phosphoryl]-2-phenylhex-4-enoic acid Chemical compound C=1C=CC=NC=1P(O)(=O)C(C=CC)C(C(O)=O)C1=CC=CC=C1 CNAXODRNDBZOEK-UHFFFAOYSA-N 0.000 claims 1
KGHMTMNLFRBUHA-UHFFFAOYSA-N 3-[hydroxy(pyridin-4-yl)phosphoryl]-2-phenyloctanoic acid Chemical compound C=1C=NC=CC=1P(O)(=O)C(CCCCC)C(C(O)=O)C1=CC=CC=C1 KGHMTMNLFRBUHA-UHFFFAOYSA-N 0.000 claims 1
BNFPBBFHQFBNPI-UHFFFAOYSA-N 5-[benzyl(hydroxy)phosphoryl]-2,5-dimethyl-4-naphthalen-2-ylhexanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C(CC(C)C(O)=O)C(C)(C)P(O)(=O)CC1=CC=CC=C1 BNFPBBFHQFBNPI-UHFFFAOYSA-N 0.000 claims 1
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RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
239000000439 tumor marker Substances 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
229960004982 vinblastine sulfate Drugs 0.000 description 1
KDQAABAKXDWYSZ-PNYVAJAMSA-N vinblastine sulfate Chemical compound OS(O)(=O)=O.C([C@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 KDQAABAKXDWYSZ-PNYVAJAMSA-N 0.000 description 1
229960004528 vincristine Drugs 0.000 description 1
OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
238000012800 visualization Methods 0.000 description 1
210000003905 vulva Anatomy 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
239000003871 white petrolatum Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/66—Phosphorus compounds
- A61K31/661—Phosphorus acids or esters thereof not having P—C bonds, e.g. fosfosal, dichlorvos, malathion or mevinphos
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/194—Carboxylic acids, e.g. valproic acid having two or more carboxyl groups, e.g. succinic, maleic or phthalic acid
- 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
- A61K38/05—Dipeptides
- 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
- 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
- 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)
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)

AU39821/97A 1997-05-27 1997-08-15 Inhibitors of naaladase enzyme activity Ceased AU739443B2 (en)

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
US08/858985		1997-05-27
US08/863624		1997-05-27
US08/864,545 US6011021A (en)	1996-06-17	1997-05-28	Methods of cancer treatment using naaladase inhibitors
US08/864545		1997-05-28
US08/900194		1997-07-25
US08/900,194 US6025345A (en)	1996-06-17	1997-07-25	Inhibitors of NAALADase enzyme activity
PCT/US1997/014347 WO1998053812A1 (en)	1997-05-27	1997-08-15	Inhibitors of naaladase enzyme activity

Publications (2)

Publication Number	Publication Date
AU3982197A AU3982197A (en)	1998-12-30
AU739443B2 true AU739443B2 (en)	2001-10-11

Family

ID=27505934

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU39821/97A Ceased AU739443B2 (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)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU3513597A (en) *	1996-06-17	1998-01-07	Guilford Pharmaceuticals Inc.	Hydroxy-phosphinyl derivatives useful as naaladase inhibitors
AU4151897A (en) *	1996-09-27	1998-04-17	Guilford Pharmaceuticals Inc.	Pharmaceutical compositions and methods of treating compulsive disorders using naaladase inhibitors
AU4067797A (en) *	1996-09-27	1998-04-17	Eisai Inc.	Naaladase compositions and methods for treating glutamate abnormality and effecting neuronal activity in animals

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

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU3513597A (en) *	1996-06-17	1998-01-07	Guilford Pharmaceuticals Inc.	Hydroxy-phosphinyl derivatives useful as naaladase inhibitors
AU4151897A (en) *	1996-09-27	1998-04-17	Guilford Pharmaceuticals Inc.	Pharmaceutical compositions and methods of treating compulsive disorders using naaladase inhibitors
AU4067797A (en) *	1996-09-27	1998-04-17	Eisai Inc.	Naaladase compositions and methods for treating glutamate abnormality and effecting neuronal activity in animals

Also Published As

Publication number	Publication date
CA2291258A1 (en)	1998-12-03
AU3982197A (en)	1998-12-30
JP2002514158A (ja)	2002-05-14
ID20347A (id)	1998-12-03

Legal Events

Date	Code	Title	Description
2002-02-07	FGA	Letters patent sealed or granted (standard patent)

Publication	Publication Date	Title
US6046180A (en)	2000-04-04	NAALADase inhibitors
AU726854B2 (en)	2000-11-23	Certain phosphinyl derivatives useful as naaladase inhibitors
US6011021A (en)	2000-01-04	Methods of cancer treatment using naaladase inhibitors
US5804602A (en)	1998-09-08	Methods of cancer treatment using naaladase inhibitors
US5968915A (en)	1999-10-19	Naaladase inhibitors
US6025345A (en)	2000-02-15	Inhibitors of NAALADase enzyme activity
US5863536A (en)	1999-01-26	Phosphoramidate derivatives
AU749425B2 (en)	2002-06-27	Prodrugs of NAALADase inhibitors
AU733880B2 (en)	2001-05-31	Naaladase compositions and methods for treating glutamate abnormality and effecting neuronal activity in animals
US6054444A (en)	2000-04-25	Phosphonic acid derivatives
US5795877A (en)	1998-08-18	Inhibitors of NAALADase enzyme activity
AU725455B2 (en)	2000-10-12	Methods of cancer treatment using NAALADase inhibitors
EP0994707A1 (en)	2000-04-26	Inhibitors of naaladase enzyme activity
AU739443B2 (en)	2001-10-11	Inhibitors of naaladase enzyme activity
CZ390198A3 (cs)	2000-01-12	Použití inhibitoru NAALADázy při přípravě léčiva pro léčení rakoviny, potlačování růstu nádorových buněk nebo poruchy vztahující se k aktivitě enzymu NAALADázy u zvířete