JP2002514185A - ＮＡＡＬＡＤａｓｅ阻害剤を用いる強迫性障害の治療の医薬組成物及び方法 - Google Patents

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Publication number

JP2002514185A

JP2002514185A JP51563698A JP51563698A JP2002514185A JP 2002514185 A JP2002514185 A JP 2002514185A JP 51563698 A JP51563698 A JP 51563698A JP 51563698 A JP51563698 A JP 51563698A JP 2002514185 A JP2002514185 A JP 2002514185A

Authority

JP

Japan

Prior art keywords

methyl

acid

pentanedioic acid

linear

hydroxy

Prior art date

1996-09-27

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

Links

• Espacenet
• Global Dossier
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• 239000003112 inhibitor Substances 0.000 title claims abstract description 141
• 108090000369 Glutamate Carboxypeptidase II Proteins 0.000 title claims abstract description 134
• 102000003958 Glutamate Carboxypeptidase II Human genes 0.000 title claims abstract description 134
• 238000000034 method Methods 0.000 title claims abstract description 114
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 84
• 208000021384 Obsessive-Compulsive disease Diseases 0.000 title claims abstract description 19
• -1 hydroxyphosphinyl Chemical class 0.000 claims description 283
• 239000002253 acid Substances 0.000 claims description 246
• JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 245
• 239000000203 mixture Substances 0.000 claims description 117
• 125000000217 alkyl group Chemical group 0.000 claims description 116
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 112
• 125000003342 alkenyl group Chemical group 0.000 claims description 103
• 150000001875 compounds Chemical class 0.000 claims description 103
• 229910052739 hydrogen Inorganic materials 0.000 claims description 67
• 239000001257 hydrogen Substances 0.000 claims description 66
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 64
• 125000001475 halogen functional group Chemical group 0.000 claims description 63
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 59
• WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 58
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 58
• 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 51
• 229930195712 glutamate Natural products 0.000 claims description 45
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 43
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 42
• 150000003839 salts Chemical class 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 41
• 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 39
• 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 37
• 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 37
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 36
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 32
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 28
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 27
• 125000005518 carboxamido group Chemical group 0.000 claims description 27
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 26
• 239000003814 drug Substances 0.000 claims description 24
• 125000001424 substituent group Chemical group 0.000 claims description 23
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 22
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 22
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
• 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 20
• 206010013663 drug dependence Diseases 0.000 claims description 16
• WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims description 15
• 235000013922 glutamic acid Nutrition 0.000 claims description 13
• 239000004220 glutamic acid Substances 0.000 claims description 13
• 208000011117 substance-related disease Diseases 0.000 claims description 12
• 150000004677 hydrates Chemical class 0.000 claims description 10
• 230000036961 partial effect Effects 0.000 claims description 10
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 10
• AQYCMVICBNBXNA-UHFFFAOYSA-N 2-methylglutaric acid Chemical compound OC(=O)C(C)CCC(O)=O AQYCMVICBNBXNA-UHFFFAOYSA-N 0.000 claims description 9
• 208000001613 Gambling Diseases 0.000 claims description 9
• 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
• 208000007848 Alcoholism Diseases 0.000 claims description 7
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 7
• 229940124597 therapeutic agent Drugs 0.000 claims description 7
• XUHVEMSEZWOZJX-UHFFFAOYSA-N 2-(benzenesulfinylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CS(=O)C1=CC=CC=C1 XUHVEMSEZWOZJX-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• VAZDQVAVNHZARH-UHFFFAOYSA-N 2-[[hydroxy(3-phenylpropyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CCCC1=CC=CC=C1 VAZDQVAVNHZARH-UHFFFAOYSA-N 0.000 claims description 6
• 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 6
• 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 6
• 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 6
• 101800000112 Acidic peptide Proteins 0.000 claims description 6
• NTIXKJOMSSOBCE-UHFFFAOYSA-N CC1=CC=C(CP(=O)(O)CC(C)CCC)C=C1 Chemical compound CC1=CC=C(CP(=O)(O)CC(C)CCC)C=C1 NTIXKJOMSSOBCE-UHFFFAOYSA-N 0.000 claims description 6
• DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 6
• 208000000323 Tourette Syndrome Diseases 0.000 claims description 6
• 208000016620 Tourette disease Diseases 0.000 claims description 6
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
• 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 description 5
• 125000006495 3-trifluoromethyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])*)C(F)(F)F 0.000 claims description 5
• NTGPHSDEBQTYMN-UHFFFAOYSA-N FC1=C(CP(=O)(O)CC(C)CCC)C=CC=C1 Chemical compound FC1=C(CP(=O)(O)CC(C)CCC)C=CC=C1 NTGPHSDEBQTYMN-UHFFFAOYSA-N 0.000 claims description 5
• 206010057852 Nicotine dependence Diseases 0.000 claims description 5
• 206010034158 Pathological gambling Diseases 0.000 claims description 5
• 208000025569 Tobacco Use disease Diseases 0.000 claims description 5
• 201000007930 alcohol dependence Diseases 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 208000013403 hyperactivity Diseases 0.000 claims description 5
• 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 4
• 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 description 4
• ZOQVILHRYCANIG-UHFFFAOYSA-N 2-[hydroxy(methyl)phosphoryl]oxypentanedioic acid Chemical compound CP(O)(=O)OC(C(O)=O)CCC(O)=O ZOQVILHRYCANIG-UHFFFAOYSA-N 0.000 claims description 4
• VZEGIOSPGNDJBZ-UHFFFAOYSA-N 2-[hydroxy(phenyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)C1=CC=CC=C1 VZEGIOSPGNDJBZ-UHFFFAOYSA-N 0.000 claims description 4
• WQMVADYYRIKMPQ-UHFFFAOYSA-N 2-[hydroxy(propyl)phosphoryl]oxypentanedioic acid Chemical compound CCCP(O)(=O)OC(C(O)=O)CCC(O)=O WQMVADYYRIKMPQ-UHFFFAOYSA-N 0.000 claims description 4
• 208000030814 Eating disease Diseases 0.000 claims description 4
• MMNWXJGROFCJJP-UHFFFAOYSA-N FC1=CC=C(CP(=O)(O)CC(C)CCC)C=C1 Chemical compound FC1=CC=C(CP(=O)(O)CC(C)CCC)C=C1 MMNWXJGROFCJJP-UHFFFAOYSA-N 0.000 claims description 4
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 4
• KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 235000014632 disordered eating Nutrition 0.000 claims description 4
• 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 claims description 4
• 108090000765 processed proteins & peptides Proteins 0.000 claims description 4
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• AUQMJQDPBBMUKP-UHFFFAOYSA-N (4-fluorophenyl)-(2-methylpentyl)phosphinic acid Chemical compound FC1=CC=C(C=C1)P(=O)(O)CC(C)CCC AUQMJQDPBBMUKP-UHFFFAOYSA-N 0.000 claims description 3
• KSAWXSZQBLZLHL-UHFFFAOYSA-N (4-methoxyphenyl)methyl-(2-methylpentyl)phosphinic acid Chemical compound CCCC(C)CP(O)(=O)CC1=CC=C(OC)C=C1 KSAWXSZQBLZLHL-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• 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 description 3
• UBPNBZGCZKGWIK-UHFFFAOYSA-N 2-(butylsulfinylmethyl)pentanedioic acid Chemical compound CCCCS(=O)CC(C(O)=O)CCC(O)=O UBPNBZGCZKGWIK-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• NAWOQIXSDKDBEM-UHFFFAOYSA-N 2-(ethylsulfinylmethyl)pentanedioic acid Chemical compound CCS(=O)CC(C(O)=O)CCC(O)=O NAWOQIXSDKDBEM-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• YKJPKUXMGYHQKV-UHFFFAOYSA-N 2-(methylsulfinylmethyl)pentanedioic acid Chemical compound CS(=O)CC(C(O)=O)CCC(O)=O YKJPKUXMGYHQKV-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• LCQBLARAWZAJDS-UHFFFAOYSA-N 2-(phosphonomethyl)butanoic acid Chemical compound CCC(C(O)=O)CP(O)(O)=O LCQBLARAWZAJDS-UHFFFAOYSA-N 0.000 claims description 3
• XJKVZOLNPKMSQR-UHFFFAOYSA-N 2-(phosphonomethyl)hexanoic acid Chemical compound CCCCC(C(O)=O)CP(O)(O)=O XJKVZOLNPKMSQR-UHFFFAOYSA-N 0.000 claims description 3
• AGVRFHUTWFXJEA-UHFFFAOYSA-N 2-(phosphonomethyl)pentanoic acid Chemical compound CCCC(C(O)=O)CP(O)(O)=O AGVRFHUTWFXJEA-UHFFFAOYSA-N 0.000 claims description 3
• GYGXSGJIYJXSFJ-UHFFFAOYSA-N 2-(propylsulfinylmethyl)pentanedioic acid Chemical compound CCCS(=O)CC(C(O)=O)CCC(O)=O GYGXSGJIYJXSFJ-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• UTWIARBFTRTHPR-UHFFFAOYSA-N 2-(sulfinylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C=S=O UTWIARBFTRTHPR-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 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 description 3
• 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 description 3
• UIVPEQQNMNDWDC-UHFFFAOYSA-N 2-[[hydroxy(phenyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C1=CC=CC=C1 UIVPEQQNMNDWDC-UHFFFAOYSA-N 0.000 claims description 3
• WBIDFRDQHBMYJE-UHFFFAOYSA-N 2-[[hydroxy-[hydroxy(phenyl)methyl]phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C(O)C1=CC=CC=C1 WBIDFRDQHBMYJE-UHFFFAOYSA-N 0.000 claims description 3
• MXFCNMASDUEDAA-UHFFFAOYSA-N 2-[butyl(hydroxy)phosphoryl]oxypentanedioic acid Chemical compound CCCCP(O)(=O)OC(C(O)=O)CCC(O)=O MXFCNMASDUEDAA-UHFFFAOYSA-N 0.000 claims description 3
• NFNJSHKCMHAXJJ-UHFFFAOYSA-N 2-methyl-3-phosphonopropanoic acid Chemical compound OC(=O)C(C)CP(O)(O)=O NFNJSHKCMHAXJJ-UHFFFAOYSA-N 0.000 claims description 3
• ULKIYKLTKXRBOD-UHFFFAOYSA-N 2-phenyl-3-phosphonopropanoic acid Chemical compound OP(=O)(O)CC(C(=O)O)C1=CC=CC=C1 ULKIYKLTKXRBOD-UHFFFAOYSA-N 0.000 claims description 3
• 125000005975 2-phenylethyloxy group Chemical group 0.000 claims description 3
• GUXRZQZCNOHHDO-UHFFFAOYSA-N 2-phosphonopropanoic acid Chemical compound OC(=O)C(C)P(O)(O)=O GUXRZQZCNOHHDO-UHFFFAOYSA-N 0.000 claims description 3
• FZEDQPACCITSBI-UHFFFAOYSA-N 3-[hydroxy(2-methylpentyl)phosphoryl]propanoic acid Chemical compound C(=O)(O)CCP(=O)(O)CC(C)CCC FZEDQPACCITSBI-UHFFFAOYSA-N 0.000 claims description 3
• 125000005977 3-phenylpropyloxy group Chemical group 0.000 claims description 3
• HZLUOOKPCRLGNO-UHFFFAOYSA-N 3-phosphono-2-pyridin-4-ylpropanoic acid Chemical compound OP(=O)(O)CC(C(=O)O)C1=CC=NC=C1 HZLUOOKPCRLGNO-UHFFFAOYSA-N 0.000 claims description 3
• MRBJLHOXRAFBCW-UHFFFAOYSA-N 4-phenyl-2-(phosphonomethyl)butanoic acid Chemical compound OP(=O)(O)CC(C(=O)O)CCC1=CC=CC=C1 MRBJLHOXRAFBCW-UHFFFAOYSA-N 0.000 claims description 3
• NMQUCHQGNXKGTB-UHFFFAOYSA-N 5-phenyl-2-(phosphonomethyl)pentanoic acid Chemical compound OP(=O)(O)CC(C(=O)O)CCCC1=CC=CC=C1 NMQUCHQGNXKGTB-UHFFFAOYSA-N 0.000 claims description 3
• CKAJHWFHHFSCDT-WHFBIAKZSA-N Asp-Glu Chemical group OC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCC(O)=O CKAJHWFHHFSCDT-WHFBIAKZSA-N 0.000 claims description 3
• HSQFTRPNVUHTLK-LBPRGKRZSA-N C1=CC=C(C=C1)CCCP(=O)(N[C@@H](CCC(=O)N)C(=O)O)O Chemical compound C1=CC=C(C=C1)CCCP(=O)(N[C@@H](CCC(=O)N)C(=O)O)O HSQFTRPNVUHTLK-LBPRGKRZSA-N 0.000 claims description 3
• VOOMIDXCNUWGLZ-UHFFFAOYSA-N CC=1C=C(CP(=O)(O)CC(C)CCC)C=CC1 Chemical compound CC=1C=C(CP(=O)(O)CC(C)CCC)C=CC1 VOOMIDXCNUWGLZ-UHFFFAOYSA-N 0.000 claims description 3
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• 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
• 125000004076 pyridyl group Chemical group 0.000 claims description 3
• 208000011580 syndromic disease Diseases 0.000 claims description 3
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