CA2264158A1 - Compositions pharmaceutiques et methodes de traitement de troubles d'ordre compulsionnel a l'aide d'un inhibiteur de la naaladase - Google Patents
Compositions pharmaceutiques et methodes de traitement de troubles d'ordre compulsionnel a l'aide d'un inhibiteur de la naaladase Download PDFInfo
- Publication number
- CA2264158A1 CA2264158A1 CA002264158A CA2264158A CA2264158A1 CA 2264158 A1 CA2264158 A1 CA 2264158A1 CA 002264158 A CA002264158 A CA 002264158A CA 2264158 A CA2264158 A CA 2264158A CA 2264158 A1 CA2264158 A1 CA 2264158A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- pentanedioic acid
- straight
- branched chain
- 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
- 239000003112 inhibitor Substances 0.000 title claims abstract description 126
- 238000000034 method Methods 0.000 title claims abstract description 69
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 69
- 102000003958 Glutamate Carboxypeptidase II Human genes 0.000 claims abstract description 134
- 108090000369 Glutamate Carboxypeptidase II Proteins 0.000 claims abstract description 134
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 556
- -1 hydroxyphosphinyl Chemical class 0.000 claims description 212
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 192
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 143
- 125000000217 alkyl group Chemical group 0.000 claims description 115
- 239000002253 acid Substances 0.000 claims description 104
- 239000000203 mixture Substances 0.000 claims description 103
- 125000003342 alkenyl group Chemical group 0.000 claims description 88
- 150000001875 compounds Chemical class 0.000 claims description 82
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 78
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 73
- 239000001257 hydrogen Substances 0.000 claims description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims description 68
- 125000001475 halogen functional group Chemical group 0.000 claims description 64
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 61
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 61
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 61
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 53
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 49
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
- 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 42
- 229930195712 glutamate Natural products 0.000 claims description 42
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 40
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 37
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 35
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 31
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 27
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 27
- 125000005518 carboxamido group Chemical group 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 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 23
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])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 23
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 22
- 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 21
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 19
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 18
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 17
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 17
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 15
- 206010013663 drug dependence Diseases 0.000 claims description 15
- 208000011117 substance-related disease Diseases 0.000 claims description 13
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 11
- 150000004677 hydrates Chemical class 0.000 claims description 10
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 9
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 8
- 208000001613 Gambling Diseases 0.000 claims description 8
- 208000035231 inattentive type attention deficit hyperactivity disease Diseases 0.000 claims description 8
- 229940124597 therapeutic agent Drugs 0.000 claims description 7
- 101800000112 Acidic peptide Proteins 0.000 claims description 6
- 206010034158 Pathological gambling Diseases 0.000 claims description 6
- 206010057852 Nicotine dependence Diseases 0.000 claims description 5
- 208000025569 Tobacco Use disease Diseases 0.000 claims description 5
- 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
- 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 4
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 208000007848 Alcoholism Diseases 0.000 claims description 4
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 4
- 208000030814 Eating disease Diseases 0.000 claims description 4
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 4
- 201000007930 alcohol dependence Diseases 0.000 claims description 4
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
- 235000014632 disordered eating Nutrition 0.000 claims description 4
- VFPYZWRTUDAZGN-UHFFFAOYSA-N 2-(benzylsulfinylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CS(=O)CC1=CC=CC=C1 VFPYZWRTUDAZGN-UHFFFAOYSA-N 0.000 claims description 3
- XOQVDBCNWPUEPS-UHFFFAOYSA-N 2-(phosphonomethyl)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)CP(O)(O)=O XOQVDBCNWPUEPS-UHFFFAOYSA-N 0.000 claims description 3
- NNCRKIKXRSDRFI-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 NNCRKIKXRSDRFI-UHFFFAOYSA-N 0.000 claims description 3
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 3
- KOSRFJWDECSPRO-WDSKDSINSA-N Glu-Glu Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(O)=O KOSRFJWDECSPRO-WDSKDSINSA-N 0.000 claims description 3
- KOSRFJWDECSPRO-UHFFFAOYSA-N alpha-L-glutamyl-L-glutamic acid Natural products OC(=O)CCC(N)C(=O)NC(CCC(O)=O)C(O)=O KOSRFJWDECSPRO-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- OWQDWQKWSLFFFR-WDSKDSINSA-N gamma-Glu-Glu Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@H](C(O)=O)CCC(O)=O OWQDWQKWSLFFFR-WDSKDSINSA-N 0.000 claims description 3
- 108010055341 glutamyl-glutamic acid Proteins 0.000 claims description 3
- 230000003278 mimic effect Effects 0.000 claims description 3
- ZNWIUVIHLUVLTB-JTQLQIEISA-N (2s)-2-[[benzyl(hydroxy)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)NP(O)(=O)CC1=CC=CC=C1 ZNWIUVIHLUVLTB-JTQLQIEISA-N 0.000 claims 2
- QIMHASXDVZXXRJ-ZETCQYMHSA-N (2s)-2-[[butyl(hydroxy)phosphoryl]amino]pentanedioic acid Chemical compound CCCCP(O)(=O)N[C@H](C(O)=O)CCC(O)=O QIMHASXDVZXXRJ-ZETCQYMHSA-N 0.000 claims 2
- ROSYJHOMEFISAK-YFKPBYRVSA-N (2s)-2-[[ethyl(hydroxy)phosphoryl]amino]pentanedioic acid Chemical compound CCP(O)(=O)N[C@H](C(O)=O)CCC(O)=O ROSYJHOMEFISAK-YFKPBYRVSA-N 0.000 claims 2
- SVWHVKOIOWZDQX-LBPRGKRZSA-N (2s)-2-[[hydroxy(3-phenylpropyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)NP(O)(=O)CCCC1=CC=CC=C1 SVWHVKOIOWZDQX-LBPRGKRZSA-N 0.000 claims 2
- XVXVUGZUKCQIOK-BYPYZUCNSA-N (2s)-2-[[hydroxy(methyl)phosphoryl]amino]pentanedioic acid Chemical compound CP(O)(=O)N[C@H](C(O)=O)CCC(O)=O XVXVUGZUKCQIOK-BYPYZUCNSA-N 0.000 claims 2
- ZYRJKHLQJIZQAQ-JTQLQIEISA-N (2s)-2-[[hydroxy(phenyl)phosphoryl]-methylamino]pentanedioic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)N(C)P(O)(=O)C1=CC=CC=C1 ZYRJKHLQJIZQAQ-JTQLQIEISA-N 0.000 claims 2
- OXVBJVMKAPKLRB-VIFPVBQESA-N (2s)-2-[[hydroxy(phenyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)NP(O)(=O)C1=CC=CC=C1 OXVBJVMKAPKLRB-VIFPVBQESA-N 0.000 claims 2
- XQFINHZUZNLWMM-LURJTMIESA-N (2s)-2-[[hydroxy(propyl)phosphoryl]amino]pentanedioic acid Chemical compound CCCP(O)(=O)N[C@H](C(O)=O)CCC(O)=O XQFINHZUZNLWMM-LURJTMIESA-N 0.000 claims 2
- VYHUGVOVCKRCKG-UHFFFAOYSA-N 2-(2-phenylethylsulfinylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CS(=O)CCC1=CC=CC=C1 VYHUGVOVCKRCKG-UHFFFAOYSA-N 0.000 claims 2
- BFAYIORIWKEONN-UHFFFAOYSA-N 2-(2-phenylethylsulfonylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CS(=O)(=O)CCC1=CC=CC=C1 BFAYIORIWKEONN-UHFFFAOYSA-N 0.000 claims 2
- JKMKVJHRNQTGPW-UHFFFAOYSA-N 2-(3-phenylpropylsulfinylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CS(=O)CCCC1=CC=CC=C1 JKMKVJHRNQTGPW-UHFFFAOYSA-N 0.000 claims 2
- OTZATDKDOPYOAI-UHFFFAOYSA-N 2-(3-phenylpropylsulfonylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CS(=O)(=O)CCCC1=CC=CC=C1 OTZATDKDOPYOAI-UHFFFAOYSA-N 0.000 claims 2
- POAGWXMZXJQLNS-UHFFFAOYSA-N 2-(benzenesulfonylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CS(=O)(=O)C1=CC=CC=C1 POAGWXMZXJQLNS-UHFFFAOYSA-N 0.000 claims 2
- FTDAIZALXRHAIP-UHFFFAOYSA-N 2-(benzylsulfonylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CS(=O)(=O)CC1=CC=CC=C1 FTDAIZALXRHAIP-UHFFFAOYSA-N 0.000 claims 2
- UBPNBZGCZKGWIK-UHFFFAOYSA-N 2-(butylsulfinylmethyl)pentanedioic acid Chemical compound CCCCS(=O)CC(C(O)=O)CCC(O)=O UBPNBZGCZKGWIK-UHFFFAOYSA-N 0.000 claims 2
- AQLGDVIEDOXUGY-UHFFFAOYSA-N 2-(butylsulfonylmethyl)pentanedioic acid Chemical compound CCCCS(=O)(=O)CC(C(O)=O)CCC(O)=O AQLGDVIEDOXUGY-UHFFFAOYSA-N 0.000 claims 2
- NAWOQIXSDKDBEM-UHFFFAOYSA-N 2-(ethylsulfinylmethyl)pentanedioic acid Chemical compound CCS(=O)CC(C(O)=O)CCC(O)=O NAWOQIXSDKDBEM-UHFFFAOYSA-N 0.000 claims 2
- SXSQDMPJGXEWGO-UHFFFAOYSA-N 2-(ethylsulfonylmethyl)pentanedioic acid Chemical compound CCS(=O)(=O)CC(C(O)=O)CCC(O)=O SXSQDMPJGXEWGO-UHFFFAOYSA-N 0.000 claims 2
- YKJPKUXMGYHQKV-UHFFFAOYSA-N 2-(methylsulfinylmethyl)pentanedioic acid Chemical compound CS(=O)CC(C(O)=O)CCC(O)=O YKJPKUXMGYHQKV-UHFFFAOYSA-N 0.000 claims 2
- KMOWMURCEKHBKW-UHFFFAOYSA-N 2-(methylsulfonylmethyl)pentanedioic acid Chemical compound CS(=O)(=O)CC(C(O)=O)CCC(O)=O KMOWMURCEKHBKW-UHFFFAOYSA-N 0.000 claims 2
- LCQBLARAWZAJDS-UHFFFAOYSA-N 2-(phosphonomethyl)butanoic acid Chemical compound CCC(C(O)=O)CP(O)(O)=O LCQBLARAWZAJDS-UHFFFAOYSA-N 0.000 claims 2
- XJKVZOLNPKMSQR-UHFFFAOYSA-N 2-(phosphonomethyl)hexanoic acid Chemical compound CCCCC(C(O)=O)CP(O)(O)=O XJKVZOLNPKMSQR-UHFFFAOYSA-N 0.000 claims 2
- AGVRFHUTWFXJEA-UHFFFAOYSA-N 2-(phosphonomethyl)pentanoic acid Chemical compound CCCC(C(O)=O)CP(O)(O)=O AGVRFHUTWFXJEA-UHFFFAOYSA-N 0.000 claims 2
- GYGXSGJIYJXSFJ-UHFFFAOYSA-N 2-(propylsulfinylmethyl)pentanedioic acid Chemical compound CCCS(=O)CC(C(O)=O)CCC(O)=O GYGXSGJIYJXSFJ-UHFFFAOYSA-N 0.000 claims 2
- NULDUARXSZRCAX-UHFFFAOYSA-N 2-(propylsulfonylmethyl)pentanedioic acid Chemical compound CCCS(=O)(=O)CC(C(O)=O)CCC(O)=O NULDUARXSZRCAX-UHFFFAOYSA-N 0.000 claims 2
- CDALMBXQUMRRBP-UHFFFAOYSA-N 2-(pyridin-4-ylsulfinylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CS(=O)C1=CC=NC=C1 CDALMBXQUMRRBP-UHFFFAOYSA-N 0.000 claims 2
- ORVBOXYBVFKIAM-UHFFFAOYSA-N 2-(pyridin-4-ylsulfonylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CS(=O)(=O)C1=CC=NC=C1 ORVBOXYBVFKIAM-UHFFFAOYSA-N 0.000 claims 2
- UTWIARBFTRTHPR-UHFFFAOYSA-N 2-(sulfinylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C=S=O UTWIARBFTRTHPR-UHFFFAOYSA-N 0.000 claims 2
- RHPCHKVYDYPCAJ-UHFFFAOYSA-N 2-(sulfonylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C=S(=O)=O RHPCHKVYDYPCAJ-UHFFFAOYSA-N 0.000 claims 2
- PILHIJIJVLWKNF-UHFFFAOYSA-N 2-[2-(hydroxyamino)-2-oxoethyl]pentanedioic acid Chemical compound ONC(=O)CC(C(O)=O)CCC(O)=O PILHIJIJVLWKNF-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- 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 2
- ZZVRVIQJFPAVJZ-UHFFFAOYSA-N 2-[[2-aminoethyl(hydroxy)phosphoryl]methyl]pentanedioic acid Chemical compound NCCP(O)(=O)CC(C(O)=O)CCC(O)=O ZZVRVIQJFPAVJZ-UHFFFAOYSA-N 0.000 claims 2
- GZNKYXXCKRYSFH-UHFFFAOYSA-N 2-[[2-carboxyethyl(hydroxy)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CCC(O)=O GZNKYXXCKRYSFH-UHFFFAOYSA-N 0.000 claims 2
- NQDMHJIWLNJNFR-UHFFFAOYSA-N 2-[[3-aminopropyl(hydroxy)phosphoryl]methyl]pentanedioic acid Chemical compound NCCCP(O)(=O)CC(C(O)=O)CCC(O)=O NQDMHJIWLNJNFR-UHFFFAOYSA-N 0.000 claims 2
- ZSUPTWOVEHNLSW-UHFFFAOYSA-N 2-[[aminomethyl(hydroxy)phosphoryl]methyl]pentanedioic acid Chemical compound NCP(O)(=O)CC(C(O)=O)CCC(O)=O ZSUPTWOVEHNLSW-UHFFFAOYSA-N 0.000 claims 2
- KICIAQRAOHOELP-UHFFFAOYSA-N 2-[[hydroxy(2-phenylethyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CCC1=CC=CC=C1 KICIAQRAOHOELP-UHFFFAOYSA-N 0.000 claims 2
- ZLYIQDQAZHDEGA-UHFFFAOYSA-N 2-[[hydroxy(3-phenylprop-2-enyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC=CC1=CC=CC=C1 ZLYIQDQAZHDEGA-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- 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 2
- 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 2
- CHTREKLBQHLOFC-UHFFFAOYSA-N 2-[[hydroxy-[(4-methoxyphenyl)methyl]phosphoryl]methyl]pentanedioic acid Chemical compound COC1=CC=C(CP(O)(=O)CC(CCC(O)=O)C(O)=O)C=C1 CHTREKLBQHLOFC-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 2
- OXJXOPBWKDCAHJ-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 OXJXOPBWKDCAHJ-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- PCLYIWOLCVMHAT-UHFFFAOYSA-N 2-[ethyl(hydroxy)phosphoryl]oxypentanedioic acid Chemical compound CCP(O)(=O)OC(C(O)=O)CCC(O)=O PCLYIWOLCVMHAT-UHFFFAOYSA-N 0.000 claims 2
- WBRRPOSGHSMYAO-UHFFFAOYSA-N 2-[hydroxy(3-phenylpropyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CCCC1=CC=CC=C1 WBRRPOSGHSMYAO-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 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 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 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 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 2
- FJMVEARHFIIIOY-UHFFFAOYSA-N 2-benzyl-3-phosphonopropanoic acid Chemical compound OP(=O)(O)CC(C(=O)O)CC1=CC=CC=C1 FJMVEARHFIIIOY-UHFFFAOYSA-N 0.000 claims 2
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- 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
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- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
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- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
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- C07—ORGANIC CHEMISTRY
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- 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
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- C07F9/3826—Acyclic unsaturated acids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Molecular Biology (AREA)
- Biochemistry (AREA)
- Psychiatry (AREA)
- Gastroenterology & Hepatology (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
L'invention porte sur une composition pharmaceutique et sur une méthode de traitement de troubles d'ordre compulsionnel à l'aide d'un inhibiteur de la NAALADase.
Applications Claiming Priority (19)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/718,703 | 1996-09-27 | ||
US08/718,703 US5824662A (en) | 1996-09-27 | 1996-09-27 | Treatment of global and focal ischemia using naaladase inhibitors |
US08/778,733 | 1996-12-31 | ||
US08/778,733 US5863536A (en) | 1996-12-31 | 1996-12-31 | Phosphoramidate derivatives |
US08/775,586 | 1996-12-31 | ||
US08/775,586 US5795877A (en) | 1996-12-31 | 1996-12-31 | Inhibitors of NAALADase enzyme activity |
US08/825,997 | 1997-04-04 | ||
US08/825,997 US5962521A (en) | 1997-04-04 | 1997-04-04 | Hydroxamic acid derivatives |
US08/835,572 US5902817A (en) | 1997-04-09 | 1997-04-09 | Certain sulfoxide and sulfone derivatives |
US08/835,572 | 1997-04-09 | ||
US08/842,360 US6054444A (en) | 1997-04-24 | 1997-04-24 | Phosphonic acid derivatives |
US08/842,360 | 1997-04-24 | ||
US08/863,624 | 1997-05-27 | ||
US08/858,985 US6025344A (en) | 1996-06-17 | 1997-05-27 | Certain dioic acid derivatives useful as NAALADase inhibitors |
US08/863,624 US6046180A (en) | 1996-06-17 | 1997-05-27 | NAALADase inhibitors |
US08/858,985 | 1997-05-27 | ||
US08/884,479 | 1997-06-27 | ||
US08/884,479 US6017903A (en) | 1996-09-27 | 1997-06-27 | Pharmaceutical compositions and methods of treating a glutamate abnormality and effecting a neuronal activity in an animal using NAALADase inhibitors |
PCT/US1997/014417 WO1998013044A1 (fr) | 1996-09-27 | 1997-08-15 | Compositions pharmaceutiques et methodes de traitement de troubles d'ordre compulsionnel a l'aide d'un inhibiteur de la naaladase |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2264158A1 true CA2264158A1 (fr) | 1998-04-02 |
Family
ID=27578904
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002264158A Abandoned CA2264158A1 (fr) | 1996-09-27 | 1997-08-15 | Compositions pharmaceutiques et methodes de traitement de troubles d'ordre compulsionnel a l'aide d'un inhibiteur de la naaladase |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0949922A1 (fr) |
JP (1) | JP2002514185A (fr) |
AU (1) | AU4151897A (fr) |
CA (1) | CA2264158A1 (fr) |
ID (1) | ID18382A (fr) |
WO (1) | WO1998013044A1 (fr) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5977090A (en) * | 1996-09-27 | 1999-11-02 | Guilford Pharmaceuticals Inc. | Pharmaceutical compositions and methods of treating compulsive disorders using NAALADase inhibitors |
US6071965A (en) * | 1996-06-17 | 2000-06-06 | Guilford Pharmaceuticals Inc. | Phosphinic alkanoic acid derivatives |
US6054444A (en) * | 1997-04-24 | 2000-04-25 | Guilford Pharmaceuticals Inc. | Phosphonic acid derivatives |
US5962521A (en) * | 1997-04-04 | 1999-10-05 | Guilford Pharmaceuticals Inc. | Hydroxamic acid derivatives |
WO1998053812A1 (fr) * | 1997-05-27 | 1998-12-03 | Guilford Pharmaceuticals Inc. | Inhibiteurs de l'activite enzymatique de naaladase |
ID20347A (id) * | 1997-05-27 | 1998-12-03 | Guilford Pharm Inc | Inhibitor aktifitas enzim naaladase |
CA2658200A1 (fr) * | 1998-07-06 | 2000-01-13 | Mgi Gp, Inc. | Inhibiteurs de naaladase utiles comme composes et compositions pharmaceutiques |
TR200100025T2 (tr) | 1998-07-06 | 2001-12-21 | Guilford Pharmaceuticals Inc. | Farmasötik bileşikler ve kompozisyonlar olarak faydalı naaladaz inhibitörleri. |
US6228888B1 (en) * | 1999-07-01 | 2001-05-08 | Guilford Pharmaceuticals Inc. | Methods for treating anxiety, anxiety disorders and memory impairment using naaladase inhibitors |
US6627625B1 (en) | 1999-08-16 | 2003-09-30 | Revaax Pharmaceuticals, Llc | Treatment of behavioral disorders with β-lactam compounds |
US6313159B1 (en) | 1999-08-20 | 2001-11-06 | Guilford Pharmaceuticals Inc. | Metabotropic glutamate receptor ligand derivatives as naaladase inhibitors |
RU2323223C2 (ru) * | 2002-03-21 | 2008-04-27 | Шеринг Акциенгезельшафт | Ингибиторы карбоксипептидазы b плазмы (крови) |
US20040186081A1 (en) * | 2003-03-03 | 2004-09-23 | Guilford Pharmaceuticals Inc. | Naaladase inhibitors for treating opioid tolerance |
US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
JP5259970B2 (ja) * | 2007-03-30 | 2013-08-07 | 学校法人九州文化学園 | 薬物依存症治療剤 |
EP2338892A1 (fr) | 2009-12-18 | 2011-06-29 | Bayer Schering Pharma Aktiengesellschaft | Inhibiteurs d'antigène de membrane spécifique à la prostate |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5500420A (en) * | 1993-12-20 | 1996-03-19 | Cornell Research Foundation, Inc. | Metabotropic glutamate receptor agonists in the treatment of cerebral ischemia |
-
1997
- 1997-08-08 ID IDP972763A patent/ID18382A/id unknown
- 1997-08-15 CA CA002264158A patent/CA2264158A1/fr not_active Abandoned
- 1997-08-15 AU AU41518/97A patent/AU4151897A/en not_active Abandoned
- 1997-08-15 WO PCT/US1997/014417 patent/WO1998013044A1/fr not_active Application Discontinuation
- 1997-08-15 JP JP51563698A patent/JP2002514185A/ja not_active Ceased
- 1997-08-15 EP EP97939427A patent/EP0949922A1/fr not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
EP0949922A1 (fr) | 1999-10-20 |
AU4151897A (en) | 1998-04-17 |
WO1998013044A1 (fr) | 1998-04-02 |
JP2002514185A (ja) | 2002-05-14 |
ID18382A (id) | 1998-04-02 |
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