LV12253B

LV12253B - Naaladāzes inhibitori un to pielietojums vēža ārstēšanai

Naaladāzes inhibitori un to pielietojums vēža ārstēšanai Download PDF

Info

Publication number: LV12253B
Authority: LV; Latvia
Prior art keywords: acid; oxy; amino; benzyloxyphosphinyl; pentanedioic
Prior art date: 1996-06-17

Application number

LVP-98-279A

Other languages

English (en)

Latvian (lv)

Other versions

LV12253A (lv

Inventor

Barbara S. Slusher

Paul F. Jackson

Kevin L. Tays

Keith M. Maclin

Original Assignee

Guilford Pharmaceuticals Inc.

Priority date

1996-06-17

Filing date

1999-02-11

Publication date

2000-01-20

1996-06-17 Priority claimed from US08/665,775 external-priority patent/US5804602A/en

1999-02-11 Application filed by Guilford Pharmaceuticals Inc. filed Critical Guilford Pharmaceuticals Inc.

1999-04-20 Publication of LV12253A publication Critical patent/LV12253A/xx

2000-01-20 Publication of LV12253B publication Critical patent/LV12253B/lv

Links

239000003112 inhibitor Substances 0.000 title claims description 141
206010028980 Neoplasm Diseases 0.000 title claims description 120
201000011510 cancer Diseases 0.000 title claims description 51
-1 hydroxyphosphinyl Chemical class 0.000 claims abstract description 774
150000001875 compounds Chemical class 0.000 claims abstract description 145
238000000034 method Methods 0.000 claims abstract description 48
206010060862 Prostate cancer Diseases 0.000 claims abstract description 43
208000000236 Prostatic Neoplasms Diseases 0.000 claims abstract description 40
230000000694 effects Effects 0.000 claims abstract description 39
208000017497 prostate disease Diseases 0.000 claims abstract description 13
JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 313
108090000369 Glutamate Carboxypeptidase II Proteins 0.000 claims description 167
239000000203 mixture Substances 0.000 claims description 142
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 122
238000011282 treatment Methods 0.000 claims description 88
239000002253 acid Substances 0.000 claims description 85
125000003342 alkenyl group Chemical group 0.000 claims description 77
125000000217 alkyl group Chemical group 0.000 claims description 75
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 69
150000003839 salts Chemical class 0.000 claims description 68
125000000392 cycloalkenyl group Chemical group 0.000 claims description 63
210000004027 cell Anatomy 0.000 claims description 42
ISEYJGQFXSTPMQ-UHFFFAOYSA-N 2-(phosphonomethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(O)=O ISEYJGQFXSTPMQ-UHFFFAOYSA-N 0.000 claims description 39
125000000753 cycloalkyl group Chemical class 0.000 claims description 39
125000001931 aliphatic group Chemical group 0.000 claims description 38
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 37
150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 36
125000003118 aryl group Chemical class 0.000 claims description 35
125000002837 carbocyclic group Chemical group 0.000 claims description 35
239000000126 substance Substances 0.000 claims description 35
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 34
125000000623 heterocyclic group Chemical group 0.000 claims description 33
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 28
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 28
239000003814 drug Substances 0.000 claims description 28
241001465754 Metazoa Species 0.000 claims description 27
239000001257 hydrogen Substances 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 25
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 24
150000002431 hydrogen Chemical class 0.000 claims description 24
238000002347 injection Methods 0.000 claims description 23
239000007924 injection Substances 0.000 claims description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 21
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 21
239000001301 oxygen Substances 0.000 claims description 21
229910052760 oxygen Inorganic materials 0.000 claims description 21
125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 20
LGBHWCHYODMSKL-UHFFFAOYSA-N 2-[[(2-fluorophenyl)methyl-hydroxyphosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC1=CC=CC=C1F LGBHWCHYODMSKL-UHFFFAOYSA-N 0.000 claims description 17
230000002401 inhibitory effect Effects 0.000 claims description 17
229940088597 hormone Drugs 0.000 claims description 16
239000005556 hormone Substances 0.000 claims description 16
CYVJVQLEPWFFCF-UHFFFAOYSA-N 2-[(2-fluorophenyl)methyl-hydroxyphosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1=CC=CC=C1F CYVJVQLEPWFFCF-UHFFFAOYSA-N 0.000 claims description 15
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 15
125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 14
KKGSCLRYTMKKLP-UHFFFAOYSA-N 2-(phosphonoamino)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(O)=O KKGSCLRYTMKKLP-UHFFFAOYSA-N 0.000 claims description 14
CAGAVCIHAJPIJR-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]methyl]pentanedioic acid Chemical compound CP(O)(=O)CC(C(O)=O)CCC(O)=O CAGAVCIHAJPIJR-UHFFFAOYSA-N 0.000 claims description 14
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 14
HCNFYUWPTGVLOQ-UHFFFAOYSA-N 3-[hydroxy(thiophen-3-yl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)C=1C=CSC=1 HCNFYUWPTGVLOQ-UHFFFAOYSA-N 0.000 claims description 14
XVXVUGZUKCQIOK-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]amino]pentanedioic acid Chemical compound CP(O)(=O)NC(C(O)=O)CCC(O)=O XVXVUGZUKCQIOK-UHFFFAOYSA-N 0.000 claims description 13
RWTNGNACMXDVQP-UHFFFAOYSA-N 2-[[hydroxy(thiophen-3-ylmethyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC=1C=CSC=1 RWTNGNACMXDVQP-UHFFFAOYSA-N 0.000 claims description 13
BUIODKODJCEWRF-UHFFFAOYSA-N 2-[hydroxy(thiophen-3-ylmethyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC=1C=CSC=1 BUIODKODJCEWRF-UHFFFAOYSA-N 0.000 claims description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
DKFCZKUFXCMIAP-UHFFFAOYSA-N 2-[[(2-fluorophenyl)methyl-hydroxyphosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1=CC=CC=C1F DKFCZKUFXCMIAP-UHFFFAOYSA-N 0.000 claims description 12
XPTOUPHGGSTLHI-UHFFFAOYSA-N 2-[[(4-fluorophenyl)-hydroxyphosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)C1=CC=C(F)C=C1 XPTOUPHGGSTLHI-UHFFFAOYSA-N 0.000 claims description 12
POLVGRCQKICNOH-UHFFFAOYSA-N 2-[[(4-fluorophenyl)methyl-hydroxyphosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1=CC=C(F)C=C1 POLVGRCQKICNOH-UHFFFAOYSA-N 0.000 claims description 12
OYVOQEGFXVKTIL-UHFFFAOYSA-N 2-[[(4-fluorophenyl)methyl-hydroxyphosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC1=CC=C(F)C=C1 OYVOQEGFXVKTIL-UHFFFAOYSA-N 0.000 claims description 12
LEXGADWOXKHTNB-UHFFFAOYSA-N 2-[[hydroxy(thiophen-3-yl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)C=1C=CSC=1 LEXGADWOXKHTNB-UHFFFAOYSA-N 0.000 claims description 12
MBPGRTVAJROGND-UHFFFAOYSA-N 2-[[hydroxy(thiophen-3-yl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)C=1C=CSC=1 MBPGRTVAJROGND-UHFFFAOYSA-N 0.000 claims description 12
XDWMYTGFURHDOA-UHFFFAOYSA-N 2-[[hydroxy(thiophen-3-yl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C=1C=CSC=1 XDWMYTGFURHDOA-UHFFFAOYSA-N 0.000 claims description 12
DEFHYMRFBAYION-UHFFFAOYSA-N 2-[[hydroxy(thiophen-3-ylmethyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CC=1C=CSC=1 DEFHYMRFBAYION-UHFFFAOYSA-N 0.000 claims description 12
KWUQXTWAEHRRNT-UHFFFAOYSA-N 2-[[hydroxy-[(3-methylphenyl)methyl]phosphoryl]methyl]pentanedioic acid Chemical compound CC1=CC=CC(CP(O)(=O)CC(CCC(O)=O)C(O)=O)=C1 KWUQXTWAEHRRNT-UHFFFAOYSA-N 0.000 claims description 12
ZOQVILHRYCANIG-UHFFFAOYSA-N 2-[hydroxy(methyl)phosphoryl]oxypentanedioic acid Chemical compound CP(O)(=O)OC(C(O)=O)CCC(O)=O ZOQVILHRYCANIG-UHFFFAOYSA-N 0.000 claims description 12
YZGBWFOXCWDWSP-UHFFFAOYSA-N 2-[hydroxy(thiophen-3-yl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)C=1C=CSC=1 YZGBWFOXCWDWSP-UHFFFAOYSA-N 0.000 claims description 12
JJKOBUUDRGAVEK-UHFFFAOYSA-N 2-[hydroxy-[[3-(trifluoromethyl)phenyl]methyl]phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1=CC=CC(C(F)(F)F)=C1 JJKOBUUDRGAVEK-UHFFFAOYSA-N 0.000 claims description 12
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 12
201000005825 prostate adenocarcinoma Diseases 0.000 claims description 12
IDPMTZKPKDZJNV-UHFFFAOYSA-N 2-[(4-fluorophenyl)methyl-hydroxyphosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1=CC=C(F)C=C1 IDPMTZKPKDZJNV-UHFFFAOYSA-N 0.000 claims description 11
JCNLQFPTNJDDBA-UHFFFAOYSA-N 2-[[(4-fluorophenyl)-hydroxyphosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C1=CC=C(F)C=C1 JCNLQFPTNJDDBA-UHFFFAOYSA-N 0.000 claims description 11
DOFBJKROBHLNQF-UHFFFAOYSA-N 2-[[hydroxy-[(2,3,4,5,6-pentafluorophenyl)methyl]phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1=C(F)C(F)=C(F)C(F)=C1F DOFBJKROBHLNQF-UHFFFAOYSA-N 0.000 claims description 11
PEUZLKMPHXDVCI-UHFFFAOYSA-N 2-[[hydroxy-[(3-methylphenyl)methyl]phosphoryl]amino]pentanedioic acid Chemical compound CC1=CC=CC(CP(O)(=O)NC(CCC(O)=O)C(O)=O)=C1 PEUZLKMPHXDVCI-UHFFFAOYSA-N 0.000 claims description 11
SWBDJEOHCFZCCJ-UHFFFAOYSA-N 2-[[hydroxy-[(4-methylphenyl)methyl]phosphoryl]amino]pentanedioic acid Chemical compound CC1=CC=C(CP(O)(=O)NC(CCC(O)=O)C(O)=O)C=C1 SWBDJEOHCFZCCJ-UHFFFAOYSA-N 0.000 claims description 11
ARSRTTFMMOQPTN-UHFFFAOYSA-N 2-[[hydroxy-[(4-methylphenyl)methyl]phosphoryl]methyl]pentanedioic acid Chemical compound CC1=CC=C(CP(O)(=O)CC(CCC(O)=O)C(O)=O)C=C1 ARSRTTFMMOQPTN-UHFFFAOYSA-N 0.000 claims description 11
FNMLFPXOJJFXCA-UHFFFAOYSA-N 2-[[hydroxy-[[3-(trifluoromethyl)phenyl]methyl]phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC1=CC=CC(C(F)(F)F)=C1 FNMLFPXOJJFXCA-UHFFFAOYSA-N 0.000 claims description 11
BQMIDMUGWWSPMB-UHFFFAOYSA-N 2-[hydroxy(thiophen-3-ylmethyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CC=1C=CSC=1 BQMIDMUGWWSPMB-UHFFFAOYSA-N 0.000 claims description 11
RCESSRYCLKVLRD-UHFFFAOYSA-N 2-[hydroxy-[(3-methylphenyl)methyl]phosphoryl]oxypentanedioic acid Chemical compound CC1=CC=CC(CP(O)(=O)OC(CCC(O)=O)C(O)=O)=C1 RCESSRYCLKVLRD-UHFFFAOYSA-N 0.000 claims description 11
MZGBIOWKDIUFFG-UHFFFAOYSA-N 2-phosphonooxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(O)=O MZGBIOWKDIUFFG-UHFFFAOYSA-N 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
125000001424 substituent group Chemical group 0.000 claims description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
XAZZWLYWTWPPNL-UHFFFAOYSA-N 2-[(4-fluorophenyl)-hydroxyphosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)C1=CC=C(F)C=C1 XAZZWLYWTWPPNL-UHFFFAOYSA-N 0.000 claims description 10
WSHKRHNRJNQHLM-UHFFFAOYSA-N 2-[[hydroxy(2-phenylethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CCC1=CC=CC=C1 WSHKRHNRJNQHLM-UHFFFAOYSA-N 0.000 claims description 10
YECLUONKYCPSNK-UHFFFAOYSA-N 2-[[hydroxy-[[3-(trifluoromethyl)phenyl]methyl]phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1=CC=CC(C(F)(F)F)=C1 YECLUONKYCPSNK-UHFFFAOYSA-N 0.000 claims description 10
KQSJGWUTRARGLX-UHFFFAOYSA-N 2-[hydroxy(thiophen-3-yl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)C=1C=CSC=1 KQSJGWUTRARGLX-UHFFFAOYSA-N 0.000 claims description 10
PKAHXOUYUIICIV-UHFFFAOYSA-N 3-[hydroxy(thiophen-3-ylmethyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CC=1C=CSC=1 PKAHXOUYUIICIV-UHFFFAOYSA-N 0.000 claims description 10
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 10
208000024313 Testicular Neoplasms Diseases 0.000 claims description 10
206010057644 Testis cancer Diseases 0.000 claims description 10
150000002306 glutamic acid derivatives Chemical class 0.000 claims description 10
229920000642 polymer Polymers 0.000 claims description 10
201000003120 testicular cancer Diseases 0.000 claims description 10
230000004565 tumor cell growth Effects 0.000 claims description 10
GUNCDQWGJVZRFS-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]amino]hexanedioic acid Chemical compound CP(O)(=O)NC(C(O)=O)CCCC(O)=O GUNCDQWGJVZRFS-UHFFFAOYSA-N 0.000 claims description 9
SVAHMQCUSNJPRX-UHFFFAOYSA-N 2-[[hydroxy-[(2,3,4,5,6-pentafluorophenyl)methyl]phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC1=C(F)C(F)=C(F)C(F)=C1F SVAHMQCUSNJPRX-UHFFFAOYSA-N 0.000 claims description 9
MZTCYOOMRRHYLS-UHFFFAOYSA-N 2-[hydroxy-[(2,3,4,5,6-pentafluorophenyl)methyl]phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1=C(F)C(F)=C(F)C(F)=C1F MZTCYOOMRRHYLS-UHFFFAOYSA-N 0.000 claims description 9
208000003174 Brain Neoplasms Diseases 0.000 claims description 9
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 9
206010058467 Lung neoplasm malignant Diseases 0.000 claims description 9
201000005202 lung cancer Diseases 0.000 claims description 9
208000020816 lung neoplasm Diseases 0.000 claims description 9
230000001225 therapeutic effect Effects 0.000 claims description 9
BMHKVATTWSSGNF-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]methyl]hexanedioic acid Chemical compound CP(O)(=O)CC(C(O)=O)CCCC(O)=O BMHKVATTWSSGNF-UHFFFAOYSA-N 0.000 claims description 8
XXWXITBUQFYWJL-UHFFFAOYSA-N 2-[hydroxy(methyl)phosphoryl]oxyhexanedioic acid Chemical compound CP(O)(=O)OC(C(O)=O)CCCC(O)=O XXWXITBUQFYWJL-UHFFFAOYSA-N 0.000 claims description 8
JEYKSCFWVYRLMS-UHFFFAOYSA-N 2-[hydroxy(naphthalen-2-yl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1P(O)(=O)OC(C(=O)O)C1=CC=CC=C1 JEYKSCFWVYRLMS-UHFFFAOYSA-N 0.000 claims description 8
VFRDKQXHIWLNCO-UHFFFAOYSA-N 2-[hydroxy-[(4-methylphenyl)methyl]phosphoryl]oxypentanedioic acid Chemical compound CC1=CC=C(CP(O)(=O)OC(CCC(O)=O)C(O)=O)C=C1 VFRDKQXHIWLNCO-UHFFFAOYSA-N 0.000 claims description 8
RTYBLIQDONZPNL-UHFFFAOYSA-N 3-[hydroxy(2-naphthalen-2-ylethyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1CCP(O)(=O)CC(C(=O)O)C1=CC=CC=C1 RTYBLIQDONZPNL-UHFFFAOYSA-N 0.000 claims description 8
208000008839 Kidney Neoplasms Diseases 0.000 claims description 8
206010033128 Ovarian cancer Diseases 0.000 claims description 8
206010061535 Ovarian neoplasm Diseases 0.000 claims description 8
206010038389 Renal cancer Diseases 0.000 claims description 8
206010039491 Sarcoma Diseases 0.000 claims description 8
201000010982 kidney cancer Diseases 0.000 claims description 8
229940124597 therapeutic agent Drugs 0.000 claims description 8
FZQWPLKMYLFIKA-UHFFFAOYSA-N 2-[[cyclohexylmethyl(hydroxy)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1CCCCC1 FZQWPLKMYLFIKA-UHFFFAOYSA-N 0.000 claims description 7
ROSYJHOMEFISAK-UHFFFAOYSA-N 2-[[ethyl(hydroxy)phosphoryl]amino]pentanedioic acid Chemical compound CCP(O)(=O)NC(C(O)=O)CCC(O)=O ROSYJHOMEFISAK-UHFFFAOYSA-N 0.000 claims description 7
LZPVIXHUAAWJOK-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-3-yl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1NC2=CC=CC=C2C=1P(O)(=O)NC(C(=O)O)C1=CC=CC=C1 LZPVIXHUAAWJOK-UHFFFAOYSA-N 0.000 claims description 7
YJKMOBFDMKUCIQ-UHFFFAOYSA-N 2-[[hydroxy(2-naphthalen-1-ylethyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2C(CCP(O)(=O)NC(CCC(=O)O)C(O)=O)=CC=CC2=C1 YJKMOBFDMKUCIQ-UHFFFAOYSA-N 0.000 claims description 7
USGMAULOBKQKPP-UHFFFAOYSA-N 2-[[hydroxy(2-pyridin-3-ylethyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CCC1=CC=CN=C1 USGMAULOBKQKPP-UHFFFAOYSA-N 0.000 claims description 7
OTVGVLFWANCUOJ-UHFFFAOYSA-N 2-[[hydroxy(2-thiophen-3-ylethyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CCC=1C=CSC=1 OTVGVLFWANCUOJ-UHFFFAOYSA-N 0.000 claims description 7
CHLUVBQWLGWEKB-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound CP(O)(=O)NC(C(O)=O)C1=CC=CC=C1 CHLUVBQWLGWEKB-UHFFFAOYSA-N 0.000 claims description 7
CQTHZXYSMZNMKV-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]amino]decanedioic acid Chemical compound CP(O)(=O)NC(C(O)=O)CCCCCCCC(O)=O CQTHZXYSMZNMKV-UHFFFAOYSA-N 0.000 claims description 7
XBFRRBVIIUORHE-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]amino]heptanedioic acid Chemical compound CP(O)(=O)NC(C(O)=O)CCCCC(O)=O XBFRRBVIIUORHE-UHFFFAOYSA-N 0.000 claims description 7
NPVGHZOJXNTGBD-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]amino]nonanedioic acid Chemical compound CP(O)(=O)NC(C(O)=O)CCCCCCC(O)=O NPVGHZOJXNTGBD-UHFFFAOYSA-N 0.000 claims description 7
XASUMCCMQXASNX-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]methyl]decanedioic acid Chemical compound CP(O)(=O)CC(C(O)=O)CCCCCCCC(O)=O XASUMCCMQXASNX-UHFFFAOYSA-N 0.000 claims description 7
IHMUNYQWPXGHMI-UHFFFAOYSA-N 2-[[hydroxy(naphthalen-1-yl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=C2C(P(O)(=O)CC(CCC(=O)O)C(O)=O)=CC=CC2=C1 IHMUNYQWPXGHMI-UHFFFAOYSA-N 0.000 claims description 7
GKHDJEWVCLDLKH-UHFFFAOYSA-N 2-[[hydroxy(naphthalen-1-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2C(CP(O)(=O)NC(CCC(=O)O)C(O)=O)=CC=CC2=C1 GKHDJEWVCLDLKH-UHFFFAOYSA-N 0.000 claims description 7
WTEDQNTZBJLCHS-UHFFFAOYSA-N 2-[[hydroxy(naphthalen-2-yl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=CC2=CC(P(O)(=O)NC(CCC(=O)O)C(O)=O)=CC=C21 WTEDQNTZBJLCHS-UHFFFAOYSA-N 0.000 claims description 7
OQIMAIQFPFTKMH-UHFFFAOYSA-N 2-[[hydroxy(naphthalen-2-yl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=CC2=CC(P(O)(=O)CC(CCC(=O)O)C(O)=O)=CC=C21 OQIMAIQFPFTKMH-UHFFFAOYSA-N 0.000 claims description 7
DUISQPJAGXKTMQ-UHFFFAOYSA-N 2-[[hydroxy(naphthalen-2-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=CC2=CC(CP(O)(=O)NC(CCC(=O)O)C(O)=O)=CC=C21 DUISQPJAGXKTMQ-UHFFFAOYSA-N 0.000 claims description 7
AFHIKLMEAGJTCO-UHFFFAOYSA-N 2-[[hydroxy(oxolan-2-yl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)C1CCCO1 AFHIKLMEAGJTCO-UHFFFAOYSA-N 0.000 claims description 7
LCTSSROJTJQOLC-UHFFFAOYSA-N 2-[[hydroxy(pyridin-2-yl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)C1=CC=CC=N1 LCTSSROJTJQOLC-UHFFFAOYSA-N 0.000 claims description 7
UBAPABGTVZNJKC-UHFFFAOYSA-N 2-[[hydroxy(pyridin-3-ylmethyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CC1=CC=CN=C1 UBAPABGTVZNJKC-UHFFFAOYSA-N 0.000 claims description 7
HJDHHXUMBDCJHS-UHFFFAOYSA-N 2-[[hydroxy(pyridin-4-yl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C1=CC=NC=C1 HJDHHXUMBDCJHS-UHFFFAOYSA-N 0.000 claims description 7
WIJGRKWAABBWJZ-UHFFFAOYSA-N 2-[[hydroxy(pyridin-4-ylmethyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC1=CC=NC=C1 WIJGRKWAABBWJZ-UHFFFAOYSA-N 0.000 claims description 7
KXSXZLZCTZZCMA-UHFFFAOYSA-N 2-[[hydroxy-(2,3,4-trimethoxyphenyl)phosphoryl]amino]pentanedioic acid Chemical compound COC1=CC=C(P(O)(=O)NC(CCC(O)=O)C(O)=O)C(OC)=C1OC KXSXZLZCTZZCMA-UHFFFAOYSA-N 0.000 claims description 7
AYXQYBIHRBILHT-UHFFFAOYSA-N 2-[cyclohexylmethyl(hydroxy)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1CCCCC1 AYXQYBIHRBILHT-UHFFFAOYSA-N 0.000 claims description 7
OYHRRCVVKGCOEJ-UHFFFAOYSA-N 2-[ethyl(hydroxy)phosphoryl]oxy-2-phenylacetic acid Chemical compound CCP(O)(=O)OC(C(O)=O)C1=CC=CC=C1 OYHRRCVVKGCOEJ-UHFFFAOYSA-N 0.000 claims description 7
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 7
KBLSQDALNZVFSZ-UHFFFAOYSA-N 2-[hydroxy(1h-indol-2-ylmethyl)phosphoryl]oxypentanedioic acid Chemical compound C1=CC=C2NC(CP(O)(=O)OC(CCC(=O)O)C(O)=O)=CC2=C1 KBLSQDALNZVFSZ-UHFFFAOYSA-N 0.000 claims description 7
RBOXLRSRSHKVNQ-UHFFFAOYSA-N 2-[hydroxy(1h-indol-3-yl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1NC2=CC=CC=C2C=1P(O)(=O)OC(C(=O)O)C1=CC=CC=C1 RBOXLRSRSHKVNQ-UHFFFAOYSA-N 0.000 claims description 7
PYPNGRDUVCDRQD-UHFFFAOYSA-N 2-[hydroxy(2-naphthalen-1-ylethyl)phosphoryl]oxypentanedioic acid Chemical compound C1=CC=C2C(CCP(O)(=O)OC(CCC(=O)O)C(O)=O)=CC=CC2=C1 PYPNGRDUVCDRQD-UHFFFAOYSA-N 0.000 claims description 7
BDERLMQTYSTSKB-UHFFFAOYSA-N 2-[hydroxy(2-naphthalen-2-ylethyl)phosphoryl]oxypentanedioic acid Chemical compound C1=CC=CC2=CC(CCP(O)(=O)OC(CCC(=O)O)C(O)=O)=CC=C21 BDERLMQTYSTSKB-UHFFFAOYSA-N 0.000 claims description 7
VYJUMDFZIDPXEN-UHFFFAOYSA-N 2-[hydroxy(2-phenylethyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CCC1=CC=CC=C1 VYJUMDFZIDPXEN-UHFFFAOYSA-N 0.000 claims description 7
AWGNGJXYRMWRFM-UHFFFAOYSA-N 2-[hydroxy(methyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound CP(O)(=O)OC(C(O)=O)C1=CC=CC=C1 AWGNGJXYRMWRFM-UHFFFAOYSA-N 0.000 claims description 7
CHPHABXBSZGJRE-UHFFFAOYSA-N 2-[hydroxy(naphthalen-2-ylmethyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1CP(O)(=O)OC(C(=O)O)C1=CC=CC=C1 CHPHABXBSZGJRE-UHFFFAOYSA-N 0.000 claims description 7
ZRJWPYMQYLVPBV-UHFFFAOYSA-N 2-[hydroxy(oxolan-2-ylmethyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CC1CCCO1 ZRJWPYMQYLVPBV-UHFFFAOYSA-N 0.000 claims description 7
GNZHIXUXUJTXFO-UHFFFAOYSA-N 2-[hydroxy(oxolan-2-ylmethyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1CCCO1 GNZHIXUXUJTXFO-UHFFFAOYSA-N 0.000 claims description 7
PEGPIKSYOWTXQJ-UHFFFAOYSA-N 2-[hydroxy(thiophen-2-ylmethyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1=CC=CS1 PEGPIKSYOWTXQJ-UHFFFAOYSA-N 0.000 claims description 7
125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 7
PKIKLKLKJHOGIZ-UHFFFAOYSA-N 3-[cyclohexylmethyl(hydroxy)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CC1CCCCC1 PKIKLKLKJHOGIZ-UHFFFAOYSA-N 0.000 claims description 7
JXOVCUHIDFZDKY-UHFFFAOYSA-N 3-[ethyl(hydroxy)phosphoryl]-2-phenylpropanoic acid Chemical compound CCP(O)(=O)CC(C(O)=O)C1=CC=CC=C1 JXOVCUHIDFZDKY-UHFFFAOYSA-N 0.000 claims description 7
TZBXLJKORLEPGT-UHFFFAOYSA-N 3-[hydroxy(1h-indol-3-yl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1NC2=CC=CC=C2C=1P(O)(=O)CC(C(=O)O)C1=CC=CC=C1 TZBXLJKORLEPGT-UHFFFAOYSA-N 0.000 claims description 7
LYAHMLXANDDJGO-UHFFFAOYSA-N 3-[hydroxy(1h-indol-4-yl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=2NC=CC=2C=1P(O)(=O)CC(C(=O)O)C1=CC=CC=C1 LYAHMLXANDDJGO-UHFFFAOYSA-N 0.000 claims description 7
JKNBEIUCTKZGSW-UHFFFAOYSA-N 3-[hydroxy(2-naphthalen-1-ylethyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1CCP(O)(=O)CC(C(=O)O)C1=CC=CC=C1 JKNBEIUCTKZGSW-UHFFFAOYSA-N 0.000 claims description 7
KBRGTEORAHEMGA-UHFFFAOYSA-N 3-[hydroxy(methyl)phosphoryl]-2-phenylpropanoic acid Chemical compound CP(O)(=O)CC(C(O)=O)C1=CC=CC=C1 KBRGTEORAHEMGA-UHFFFAOYSA-N 0.000 claims description 7
KEYDVRLBRBOTLF-UHFFFAOYSA-N 3-[hydroxy(oxolan-2-yl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)C1CCCO1 KEYDVRLBRBOTLF-UHFFFAOYSA-N 0.000 claims description 7
LZMZNBCVXZXIJD-UHFFFAOYSA-N 3-[hydroxy(pyridin-4-yl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)C1=CC=NC=C1 LZMZNBCVXZXIJD-UHFFFAOYSA-N 0.000 claims description 7
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 7
206010005003 Bladder cancer Diseases 0.000 claims description 7
239000000055 Corticotropin-Releasing Hormone Substances 0.000 claims description 7
208000017604 Hodgkin disease Diseases 0.000 claims description 7
208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims description 7
IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 claims description 7
229960000258 corticotropin Drugs 0.000 claims description 7
150000004677 hydrates Chemical class 0.000 claims description 7
201000005112 urinary bladder cancer Diseases 0.000 claims description 7
ABNFNHOCZNGSGT-UHFFFAOYSA-N 2-[[cyclohexylmethyl(hydroxy)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CC1CCCCC1 ABNFNHOCZNGSGT-UHFFFAOYSA-N 0.000 claims description 6
ZDECCUDWIMXEKV-UHFFFAOYSA-N 2-[[ethyl(hydroxy)phosphoryl]methyl]pentanedioic acid Chemical compound CCP(O)(=O)CC(C(O)=O)CCC(O)=O ZDECCUDWIMXEKV-UHFFFAOYSA-N 0.000 claims description 6
ZRZUROGIYXZCQD-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-2-yl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C2=CC=CC=C2NC=1P(O)(=O)NC(C(=O)O)C1=CC=CC=C1 ZRZUROGIYXZCQD-UHFFFAOYSA-N 0.000 claims description 6
UOCDCEAACFTUGK-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-2-yl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=C2NC(P(O)(=O)CC(CCC(=O)O)C(O)=O)=CC2=C1 UOCDCEAACFTUGK-UHFFFAOYSA-N 0.000 claims description 6
JXSAXAANCGGELN-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-2-ylmethyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C2=CC=CC=C2NC=1CP(O)(=O)NC(C(=O)O)C1=CC=CC=C1 JXSAXAANCGGELN-UHFFFAOYSA-N 0.000 claims description 6
IQIHLRSQIUDWQI-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-3-yl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2C(P(O)(=O)NC(CCC(=O)O)C(O)=O)=CNC2=C1 IQIHLRSQIUDWQI-UHFFFAOYSA-N 0.000 claims description 6
QLUGCYYCTKYEPZ-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-3-yl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=C2C(P(O)(=O)CC(CCC(=O)O)C(O)=O)=CNC2=C1 QLUGCYYCTKYEPZ-UHFFFAOYSA-N 0.000 claims description 6
BVTHDJQGSGSNHX-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-3-ylmethyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1NC2=CC=CC=C2C=1CP(O)(=O)NC(C(=O)O)C1=CC=CC=C1 BVTHDJQGSGSNHX-UHFFFAOYSA-N 0.000 claims description 6
LNQXSCNPTACZTN-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-4-yl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)C1=CC=CC2=C1C=CN2 LNQXSCNPTACZTN-UHFFFAOYSA-N 0.000 claims description 6
SUWWYDJWZIKMHL-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-4-ylmethyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=2NC=CC=2C=1CP(O)(=O)NC(C(=O)O)C1=CC=CC=C1 SUWWYDJWZIKMHL-UHFFFAOYSA-N 0.000 claims description 6
XFINKTJPGWKKSU-UHFFFAOYSA-N 2-[[hydroxy(2-naphthalen-1-ylethyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC2=CC=CC=C2C=1CCP(O)(=O)NC(C(=O)O)C1=CC=CC=C1 XFINKTJPGWKKSU-UHFFFAOYSA-N 0.000 claims description 6
IPJWIGRYTYZQRI-UHFFFAOYSA-N 2-[[hydroxy(2-naphthalen-1-ylethyl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=C2C(CCP(O)(=O)CC(CCC(=O)O)C(O)=O)=CC=CC2=C1 IPJWIGRYTYZQRI-UHFFFAOYSA-N 0.000 claims description 6
NHBZMMHSNYVUQH-UHFFFAOYSA-N 2-[[hydroxy(2-naphthalen-2-ylethyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1CCP(O)(=O)NC(C(=O)O)C1=CC=CC=C1 NHBZMMHSNYVUQH-UHFFFAOYSA-N 0.000 claims description 6
QKKYNMHTSOFGLV-UHFFFAOYSA-N 2-[[hydroxy(2-naphthalen-2-ylethyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=CC2=CC(CCP(O)(=O)NC(CCC(=O)O)C(O)=O)=CC=C21 QKKYNMHTSOFGLV-UHFFFAOYSA-N 0.000 claims description 6
UNEONYJUQDOHQC-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]methyl]heptanedioic acid Chemical compound CP(O)(=O)CC(C(O)=O)CCCCC(O)=O UNEONYJUQDOHQC-UHFFFAOYSA-N 0.000 claims description 6
ICALCLLMPSHEAU-UHFFFAOYSA-N 2-[[hydroxy(naphthalen-2-ylmethyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1CP(O)(=O)NC(C(=O)O)C1=CC=CC=C1 ICALCLLMPSHEAU-UHFFFAOYSA-N 0.000 claims description 6
KBNKQJDRKPQRFZ-UHFFFAOYSA-N 2-[[hydroxy(naphthalen-2-ylmethyl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=CC2=CC(CP(O)(=O)CC(CCC(=O)O)C(O)=O)=CC=C21 KBNKQJDRKPQRFZ-UHFFFAOYSA-N 0.000 claims description 6
NBTJXRQZHKLIPE-UHFFFAOYSA-N 2-[[hydroxy(oxolan-2-yl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)C1CCCO1 NBTJXRQZHKLIPE-UHFFFAOYSA-N 0.000 claims description 6
HBXIGRUFVXBTTC-UHFFFAOYSA-N 2-[[hydroxy(oxolan-2-ylmethyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CC1CCCO1 HBXIGRUFVXBTTC-UHFFFAOYSA-N 0.000 claims description 6
WDIQUJIXMYTJNL-UHFFFAOYSA-N 2-[[hydroxy(oxolan-2-ylmethyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC1CCCO1 WDIQUJIXMYTJNL-UHFFFAOYSA-N 0.000 claims description 6
WESYMCISYFOLOV-UHFFFAOYSA-N 2-[[hydroxy(pyridin-2-yl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)C1=CC=CC=N1 WESYMCISYFOLOV-UHFFFAOYSA-N 0.000 claims description 6
GOZCMXCMCACLCK-UHFFFAOYSA-N 2-[[hydroxy(pyridin-2-yl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C1=CC=CC=N1 GOZCMXCMCACLCK-UHFFFAOYSA-N 0.000 claims description 6
BBWYLMHLVJVHJP-UHFFFAOYSA-N 2-[[hydroxy(pyridin-2-ylmethyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CC1=CC=CC=N1 BBWYLMHLVJVHJP-UHFFFAOYSA-N 0.000 claims description 6
PGAFASWIERZOFP-UHFFFAOYSA-N 2-[[hydroxy(pyridin-2-ylmethyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC1=CC=CC=N1 PGAFASWIERZOFP-UHFFFAOYSA-N 0.000 claims description 6
BLHBCGJHBNBAIQ-UHFFFAOYSA-N 2-[[hydroxy(pyridin-3-yl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C1=CC=CN=C1 BLHBCGJHBNBAIQ-UHFFFAOYSA-N 0.000 claims description 6
UKYYFDZIFLZJQF-UHFFFAOYSA-N 2-[[hydroxy(pyridin-4-yl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)C1=CC=NC=C1 UKYYFDZIFLZJQF-UHFFFAOYSA-N 0.000 claims description 6
UZQCHZMTMZCGDD-UHFFFAOYSA-N 2-[[hydroxy(pyridin-4-ylmethyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CC1=CC=NC=C1 UZQCHZMTMZCGDD-UHFFFAOYSA-N 0.000 claims description 6
WPRVGYAEIMNVLE-UHFFFAOYSA-N 2-[[hydroxy(thiophen-2-yl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)C1=CC=CS1 WPRVGYAEIMNVLE-UHFFFAOYSA-N 0.000 claims description 6
KAGMUKZRHFUGMV-UHFFFAOYSA-N 2-[[hydroxy(thiophen-2-yl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)C1=CC=CS1 KAGMUKZRHFUGMV-UHFFFAOYSA-N 0.000 claims description 6
PXFFOCTWVIACDR-UHFFFAOYSA-N 2-[[hydroxy(thiophen-2-yl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C1=CC=CS1 PXFFOCTWVIACDR-UHFFFAOYSA-N 0.000 claims description 6
CJJVDTCUDKFMEK-UHFFFAOYSA-N 2-[[hydroxy-(2,3,4-trimethoxyphenyl)phosphoryl]methyl]pentanedioic acid Chemical compound COC1=CC=C(P(O)(=O)CC(CCC(O)=O)C(O)=O)C(OC)=C1OC CJJVDTCUDKFMEK-UHFFFAOYSA-N 0.000 claims description 6
AHPQNRFTMUODJS-UHFFFAOYSA-N 2-[[hydroxy-[2-(1h-indol-3-yl)ethyl]phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=C2C(CCP(O)(=O)CC(CCC(=O)O)C(O)=O)=CNC2=C1 AHPQNRFTMUODJS-UHFFFAOYSA-N 0.000 claims description 6
RYHOYQCHTHIQLZ-UHFFFAOYSA-N 2-[[hydroxy-[2-(oxolan-2-yl)ethyl]phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CCC1CCCO1 RYHOYQCHTHIQLZ-UHFFFAOYSA-N 0.000 claims description 6
NWOKOPVQAMQFDS-UHFFFAOYSA-N 2-[[hydroxy-[methoxy(phenyl)methyl]phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)C(OC)C1=CC=CC=C1 NWOKOPVQAMQFDS-UHFFFAOYSA-N 0.000 claims description 6
HBVQNWBUEUJMIZ-UHFFFAOYSA-N 2-[[hydroxy-[methoxy(phenyl)methyl]phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C(OC)C1=CC=CC=C1 HBVQNWBUEUJMIZ-UHFFFAOYSA-N 0.000 claims description 6
OLTRDDKYXUORQL-UHFFFAOYSA-N 2-[cyclohexylmethyl(hydroxy)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CC1CCCCC1 OLTRDDKYXUORQL-UHFFFAOYSA-N 0.000 claims description 6
DGJKGLKAYJTNHS-UHFFFAOYSA-N 2-[hydroxy(1h-indol-2-yl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C2=CC=CC=C2NC=1P(O)(=O)OC(C(=O)O)C1=CC=CC=C1 DGJKGLKAYJTNHS-UHFFFAOYSA-N 0.000 claims description 6
PIBFURMMSQMXID-UHFFFAOYSA-N 2-[hydroxy(1h-indol-2-yl)phosphoryl]oxypentanedioic acid Chemical compound C1=CC=C2NC(P(O)(=O)OC(CCC(=O)O)C(O)=O)=CC2=C1 PIBFURMMSQMXID-UHFFFAOYSA-N 0.000 claims description 6
DWWDOCIKMZQJJM-UHFFFAOYSA-N 2-[hydroxy(1h-indol-2-ylmethyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C2=CC=CC=C2NC=1CP(O)(=O)OC(C(=O)O)C1=CC=CC=C1 DWWDOCIKMZQJJM-UHFFFAOYSA-N 0.000 claims description 6
GIFNYTLIJTZDJM-UHFFFAOYSA-N 2-[hydroxy(1h-indol-3-ylmethyl)phosphoryl]oxypentanedioic acid Chemical compound C1=CC=C2C(CP(O)(=O)OC(CCC(=O)O)C(O)=O)=CNC2=C1 GIFNYTLIJTZDJM-UHFFFAOYSA-N 0.000 claims description 6
HYBJBDORZWPUGX-UHFFFAOYSA-N 2-[hydroxy(1h-indol-4-yl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=2NC=CC=2C=1P(O)(=O)OC(C(=O)O)C1=CC=CC=C1 HYBJBDORZWPUGX-UHFFFAOYSA-N 0.000 claims description 6
IIYDABJZMRIVBW-UHFFFAOYSA-N 2-[hydroxy(1h-indol-4-yl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)C1=CC=CC2=C1C=CN2 IIYDABJZMRIVBW-UHFFFAOYSA-N 0.000 claims description 6
ICQQTDFDCHQKIN-UHFFFAOYSA-N 2-[hydroxy(1h-indol-4-ylmethyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=2NC=CC=2C=1CP(O)(=O)OC(C(=O)O)C1=CC=CC=C1 ICQQTDFDCHQKIN-UHFFFAOYSA-N 0.000 claims description 6
ZKGKBCIITFJESY-UHFFFAOYSA-N 2-[hydroxy(1h-indol-4-ylmethyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1=CC=CC2=C1C=CN2 ZKGKBCIITFJESY-UHFFFAOYSA-N 0.000 claims description 6
WXFQKOJDOQYUDW-UHFFFAOYSA-N 2-[hydroxy(2-pyridin-3-ylethyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CCC1=CC=CN=C1 WXFQKOJDOQYUDW-UHFFFAOYSA-N 0.000 claims description 6
RHDHLVIPRNZVMQ-UHFFFAOYSA-N 2-[hydroxy(3-phenylprop-2-enyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC=CC1=CC=CC=C1 RHDHLVIPRNZVMQ-UHFFFAOYSA-N 0.000 claims description 6
LPQJYMBUVVYRGE-UHFFFAOYSA-N 2-[hydroxy(methyl)phosphoryl]oxydecanedioic acid Chemical compound CP(O)(=O)OC(C(O)=O)CCCCCCCC(O)=O LPQJYMBUVVYRGE-UHFFFAOYSA-N 0.000 claims description 6
AFJIOKSJBSAYSS-UHFFFAOYSA-N 2-[hydroxy(methyl)phosphoryl]oxyheptanedioic acid Chemical compound CP(O)(=O)OC(C(O)=O)CCCCC(O)=O AFJIOKSJBSAYSS-UHFFFAOYSA-N 0.000 claims description 6
MVMKLPARHLWVHB-UHFFFAOYSA-N 2-[hydroxy(naphthalen-1-yl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC2=CC=CC=C2C=1P(O)(=O)OC(C(=O)O)C1=CC=CC=C1 MVMKLPARHLWVHB-UHFFFAOYSA-N 0.000 claims description 6
QBLSPVWVINZFLZ-UHFFFAOYSA-N 2-[hydroxy(naphthalen-1-yl)phosphoryl]oxypentanedioic acid Chemical compound C1=CC=C2C(P(O)(=O)OC(CCC(=O)O)C(O)=O)=CC=CC2=C1 QBLSPVWVINZFLZ-UHFFFAOYSA-N 0.000 claims description 6
BNADFKLEJDMNFF-UHFFFAOYSA-N 2-[hydroxy(naphthalen-1-ylmethyl)phosphoryl]oxypentanedioic acid Chemical compound C1=CC=C2C(CP(O)(=O)OC(CCC(=O)O)C(O)=O)=CC=CC2=C1 BNADFKLEJDMNFF-UHFFFAOYSA-N 0.000 claims description 6
FMRWBHOXQUWWPP-UHFFFAOYSA-N 2-[hydroxy(naphthalen-2-yl)phosphoryl]oxypentanedioic acid Chemical compound C1=CC=CC2=CC(P(O)(=O)OC(CCC(=O)O)C(O)=O)=CC=C21 FMRWBHOXQUWWPP-UHFFFAOYSA-N 0.000 claims description 6
BUTDWNDRYPUCNL-UHFFFAOYSA-N 2-[hydroxy(naphthalen-2-ylmethyl)phosphoryl]oxypentanedioic acid Chemical compound C1=CC=CC2=CC(CP(O)(=O)OC(CCC(=O)O)C(O)=O)=CC=C21 BUTDWNDRYPUCNL-UHFFFAOYSA-N 0.000 claims description 6
NXDCDXLCQFVLLS-UHFFFAOYSA-N 2-[hydroxy(pyridin-2-yl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)C1=CC=CC=N1 NXDCDXLCQFVLLS-UHFFFAOYSA-N 0.000 claims description 6
UEKAVTMOASYYKO-UHFFFAOYSA-N 2-[hydroxy(pyridin-2-ylmethyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CC1=CC=CC=N1 UEKAVTMOASYYKO-UHFFFAOYSA-N 0.000 claims description 6
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 description 6
RIEPOKZSCINVGV-UHFFFAOYSA-N 2-[hydroxy(pyridin-3-yl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)C1=CC=CN=C1 RIEPOKZSCINVGV-UHFFFAOYSA-N 0.000 claims description 6
IKRRTDNLTBSHCD-UHFFFAOYSA-N 2-[hydroxy(pyridin-3-ylmethyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CC1=CC=CN=C1 IKRRTDNLTBSHCD-UHFFFAOYSA-N 0.000 claims description 6
HERVSDXHCIWYTQ-UHFFFAOYSA-N 2-[hydroxy(pyridin-3-ylmethyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CC1=CC=CN=C1 HERVSDXHCIWYTQ-UHFFFAOYSA-N 0.000 claims description 6
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 description 6
HTGGUSKMTUSIAO-UHFFFAOYSA-N 2-[hydroxy(thiophen-2-yl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)C1=CC=CS1 HTGGUSKMTUSIAO-UHFFFAOYSA-N 0.000 claims description 6
LIUVGSZOQKOSDW-UHFFFAOYSA-N 2-[hydroxy(thiophen-2-yl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)C1=CC=CS1 LIUVGSZOQKOSDW-UHFFFAOYSA-N 0.000 claims description 6
SOOJACFQEJQKOR-UHFFFAOYSA-N 2-[hydroxy(thiophen-2-ylmethyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CC1=CC=CS1 SOOJACFQEJQKOR-UHFFFAOYSA-N 0.000 claims description 6
GMOARDCUHWLKGO-UHFFFAOYSA-N 2-[hydroxy-[2-(1h-indol-3-yl)ethyl]phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1NC2=CC=CC=C2C=1CCP(O)(=O)OC(C(=O)O)C1=CC=CC=C1 GMOARDCUHWLKGO-UHFFFAOYSA-N 0.000 claims description 6
KVJJFUGHAIDKKH-UHFFFAOYSA-N 2-[hydroxy-[2-(1h-indol-3-yl)ethyl]phosphoryl]oxypentanedioic acid Chemical compound C1=CC=C2C(CCP(O)(=O)OC(CCC(=O)O)C(O)=O)=CNC2=C1 KVJJFUGHAIDKKH-UHFFFAOYSA-N 0.000 claims description 6
FVRYHGIZSBPAMI-UHFFFAOYSA-N 3-[hydroxy(1h-indol-2-yl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C2=CC=CC=C2NC=1P(O)(=O)CC(C(=O)O)C1=CC=CC=C1 FVRYHGIZSBPAMI-UHFFFAOYSA-N 0.000 claims description 6
TWRJCLWKYSTOIE-UHFFFAOYSA-N 3-[hydroxy(1h-indol-2-ylmethyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C2=CC=CC=C2NC=1CP(O)(=O)CC(C(=O)O)C1=CC=CC=C1 TWRJCLWKYSTOIE-UHFFFAOYSA-N 0.000 claims description 6
PXXGAKTVAABZNG-UHFFFAOYSA-N 3-[hydroxy(1h-indol-3-ylmethyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1NC2=CC=CC=C2C=1CP(O)(=O)CC(C(=O)O)C1=CC=CC=C1 PXXGAKTVAABZNG-UHFFFAOYSA-N 0.000 claims description 6
KFUAGPLPXQFRFL-UHFFFAOYSA-N 3-[hydroxy(2-thiophen-3-ylethyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CCC=1C=CSC=1 KFUAGPLPXQFRFL-UHFFFAOYSA-N 0.000 claims description 6
PYCYXLNHUDWIPY-UHFFFAOYSA-N 3-[hydroxy(naphthalen-2-yl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1P(O)(=O)CC(C(=O)O)C1=CC=CC=C1 PYCYXLNHUDWIPY-UHFFFAOYSA-N 0.000 claims description 6
GGIBUMCNPLQUTG-UHFFFAOYSA-N 3-[hydroxy(oxolan-2-ylmethyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CC1CCCO1 GGIBUMCNPLQUTG-UHFFFAOYSA-N 0.000 claims description 6
QHGUSXYBLXSRTJ-UHFFFAOYSA-N 3-[hydroxy(pyridin-2-yl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)C1=CC=CC=N1 QHGUSXYBLXSRTJ-UHFFFAOYSA-N 0.000 claims description 6
PBNDWHDAACRHBJ-UHFFFAOYSA-N 3-[hydroxy(pyridin-3-yl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)C1=CC=CN=C1 PBNDWHDAACRHBJ-UHFFFAOYSA-N 0.000 claims description 6
PIJFGXMCSLBGQF-UHFFFAOYSA-N 3-[hydroxy(thiophen-2-yl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)C1=CC=CS1 PIJFGXMCSLBGQF-UHFFFAOYSA-N 0.000 claims description 6
KYESLLXXQLWHQA-UHFFFAOYSA-N 3-[hydroxy-[2-(oxolan-2-yl)ethyl]phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CCC1CCCO1 KYESLLXXQLWHQA-UHFFFAOYSA-N 0.000 claims description 6
208000024893 Acute lymphoblastic leukemia Diseases 0.000 claims description 6
208000014697 Acute lymphocytic leukaemia Diseases 0.000 claims description 6
208000006468 Adrenal Cortex Neoplasms Diseases 0.000 claims description 6
208000010839 B-cell chronic lymphocytic leukemia Diseases 0.000 claims description 6
208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims description 6
208000010833 Chronic myeloid leukaemia Diseases 0.000 claims description 6
206010014733 Endometrial cancer Diseases 0.000 claims description 6
206010014759 Endometrial neoplasm Diseases 0.000 claims description 6
208000000461 Esophageal Neoplasms Diseases 0.000 claims description 6
208000021519 Hodgkin lymphoma Diseases 0.000 claims description 6
208000010747 Hodgkins lymphoma Diseases 0.000 claims description 6
208000031422 Lymphocytic Chronic B-Cell Leukemia Diseases 0.000 claims description 6
208000034578 Multiple myelomas Diseases 0.000 claims description 6
208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims description 6
206010030155 Oesophageal carcinoma Diseases 0.000 claims description 6
208000002471 Penile Neoplasms Diseases 0.000 claims description 6
206010034299 Penile cancer Diseases 0.000 claims description 6
206010035226 Plasma cell myeloma Diseases 0.000 claims description 6
208000006664 Precursor Cell Lymphoblastic Leukemia-Lymphoma Diseases 0.000 claims description 6
201000000582 Retinoblastoma Diseases 0.000 claims description 6
208000000453 Skin Neoplasms Diseases 0.000 claims description 6
208000005718 Stomach Neoplasms Diseases 0.000 claims description 6
208000024770 Thyroid neoplasm Diseases 0.000 claims description 6
208000008383 Wilms tumor Diseases 0.000 claims description 6
239000004037 angiogenesis inhibitor Substances 0.000 claims description 6
230000000973 chemotherapeutic effect Effects 0.000 claims description 6
208000032852 chronic lymphocytic leukemia Diseases 0.000 claims description 6
201000004101 esophageal cancer Diseases 0.000 claims description 6
206010017758 gastric cancer Diseases 0.000 claims description 6
201000008968 osteosarcoma Diseases 0.000 claims description 6
108090000765 processed proteins & peptides Proteins 0.000 claims description 6
201000000849 skin cancer Diseases 0.000 claims description 6
201000011549 stomach cancer Diseases 0.000 claims description 6
201000002510 thyroid cancer Diseases 0.000 claims description 6
208000029387 trophoblastic neoplasm Diseases 0.000 claims description 6
208000013139 vaginal neoplasm Diseases 0.000 claims description 6
UAPXYLZVIGLACQ-UHFFFAOYSA-N 2-[[cyclohexylmethyl(hydroxy)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC1CCCCC1 UAPXYLZVIGLACQ-UHFFFAOYSA-N 0.000 claims description 5
ONQFPFIHELDZGR-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-3-ylmethyl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=C2C(CP(O)(=O)CC(CCC(=O)O)C(O)=O)=CNC2=C1 ONQFPFIHELDZGR-UHFFFAOYSA-N 0.000 claims description 5
FUJGNNYDGNFAIT-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-4-yl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=2NC=CC=2C=1P(O)(=O)NC(C(=O)O)C1=CC=CC=C1 FUJGNNYDGNFAIT-UHFFFAOYSA-N 0.000 claims description 5
PTVYFVMVEJJSSH-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-4-ylmethyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC1=CC=CC2=C1C=CN2 PTVYFVMVEJJSSH-UHFFFAOYSA-N 0.000 claims description 5
IHHCERPLCDVISF-UHFFFAOYSA-N 2-[[hydroxy(2-pyridin-3-ylethyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CCC1=CC=CN=C1 IHHCERPLCDVISF-UHFFFAOYSA-N 0.000 claims description 5
VOLHIAKJNANULA-UHFFFAOYSA-N 2-[[hydroxy(2-thiophen-3-ylethyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CCC=1C=CSC=1 VOLHIAKJNANULA-UHFFFAOYSA-N 0.000 claims description 5
XLGWLDHABQJNPF-UHFFFAOYSA-N 2-[[hydroxy(3-phenylprop-2-enyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC=CC1=CC=CC=C1 XLGWLDHABQJNPF-UHFFFAOYSA-N 0.000 claims description 5
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 description 5
ZFZBOWUYEUMIPE-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]methyl]nonanedioic acid Chemical compound CP(O)(=O)CC(C(O)=O)CCCCCCC(O)=O ZFZBOWUYEUMIPE-UHFFFAOYSA-N 0.000 claims description 5
HWZMTBBEILZTSL-UHFFFAOYSA-N 2-[[hydroxy(naphthalen-1-yl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2C(P(O)(=O)NC(CCC(=O)O)C(O)=O)=CC=CC2=C1 HWZMTBBEILZTSL-UHFFFAOYSA-N 0.000 claims description 5
VCEQZUSTJBIDMB-UHFFFAOYSA-N 2-[[hydroxy(naphthalen-1-ylmethyl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=C2C(CP(O)(=O)CC(CCC(=O)O)C(O)=O)=CC=CC2=C1 VCEQZUSTJBIDMB-UHFFFAOYSA-N 0.000 claims description 5
IBFVYDGYJGUXHU-UHFFFAOYSA-N 2-[[hydroxy(naphthalen-2-yl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1P(O)(=O)NC(C(=O)O)C1=CC=CC=C1 IBFVYDGYJGUXHU-UHFFFAOYSA-N 0.000 claims description 5
AROJVAREVHLWEB-UHFFFAOYSA-N 2-[[hydroxy(oxolan-2-yl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C1CCCO1 AROJVAREVHLWEB-UHFFFAOYSA-N 0.000 claims description 5
OCENSCUUMPQWCU-UHFFFAOYSA-N 2-[[hydroxy(pyridin-3-yl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)C1=CC=CN=C1 OCENSCUUMPQWCU-UHFFFAOYSA-N 0.000 claims description 5
JZAOSGBERFXCJI-UHFFFAOYSA-N 2-[[hydroxy(pyridin-3-yl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)C1=CC=CN=C1 JZAOSGBERFXCJI-UHFFFAOYSA-N 0.000 claims description 5
WBTFDFTYGCSKIV-UHFFFAOYSA-N 2-[[hydroxy(pyridin-4-yl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)C1=CC=NC=C1 WBTFDFTYGCSKIV-UHFFFAOYSA-N 0.000 claims description 5
OSMBRIPEOXNFDY-UHFFFAOYSA-N 2-[[hydroxy(thiophen-2-ylmethyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CC1=CC=CS1 OSMBRIPEOXNFDY-UHFFFAOYSA-N 0.000 claims description 5
PCQZQGTVIPZYSY-UHFFFAOYSA-N 2-[[hydroxy(thiophen-2-ylmethyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC1=CC=CS1 PCQZQGTVIPZYSY-UHFFFAOYSA-N 0.000 claims description 5
MBOCVNZPOKGSTN-UHFFFAOYSA-N 2-[[hydroxy(thiophen-3-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC=1C=CSC=1 MBOCVNZPOKGSTN-UHFFFAOYSA-N 0.000 claims description 5
DFTFXAPHNLAOFR-UHFFFAOYSA-N 2-[[hydroxy-[(4-methoxyphenyl)methyl]phosphoryl]amino]pentanedioic acid Chemical compound COC1=CC=C(CP(O)(=O)NC(CCC(O)=O)C(O)=O)C=C1 DFTFXAPHNLAOFR-UHFFFAOYSA-N 0.000 claims description 5
NRWBQFSKOVEQNK-UHFFFAOYSA-N 2-[[hydroxy-[2-(1h-indol-3-yl)ethyl]phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1NC2=CC=CC=C2C=1CCP(O)(=O)NC(C(=O)O)C1=CC=CC=C1 NRWBQFSKOVEQNK-UHFFFAOYSA-N 0.000 claims description 5
QZGPCPGHWPWHHK-UHFFFAOYSA-N 2-[hydroxy(1h-indol-3-yl)phosphoryl]oxypentanedioic acid Chemical compound C1=CC=C2C(P(O)(=O)OC(CCC(=O)O)C(O)=O)=CNC2=C1 QZGPCPGHWPWHHK-UHFFFAOYSA-N 0.000 claims description 5
JFMHSMYSJCKKSN-UHFFFAOYSA-N 2-[hydroxy(1h-indol-3-ylmethyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1NC2=CC=CC=C2C=1CP(O)(=O)OC(C(=O)O)C1=CC=CC=C1 JFMHSMYSJCKKSN-UHFFFAOYSA-N 0.000 claims description 5
NZZIQDPMJBMSHP-UHFFFAOYSA-N 2-[hydroxy(2-naphthalen-2-ylethyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1CCP(O)(=O)OC(C(=O)O)C1=CC=CC=C1 NZZIQDPMJBMSHP-UHFFFAOYSA-N 0.000 claims description 5
CWKULHBEECMWNV-UHFFFAOYSA-N 2-[hydroxy(2-pyridin-3-ylethyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CCC1=CC=CN=C1 CWKULHBEECMWNV-UHFFFAOYSA-N 0.000 claims description 5
IVAFJOXAOVDQND-UHFFFAOYSA-N 2-[hydroxy(2-thiophen-3-ylethyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CCC=1C=CSC=1 IVAFJOXAOVDQND-UHFFFAOYSA-N 0.000 claims description 5
RGWXCNDXNZVGNQ-UHFFFAOYSA-N 2-[hydroxy(2-thiophen-3-ylethyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CCC=1C=CSC=1 RGWXCNDXNZVGNQ-UHFFFAOYSA-N 0.000 claims description 5
BXFKTMFVBIKVQW-UHFFFAOYSA-N 2-[hydroxy(methyl)phosphoryl]oxynonanedioic acid Chemical compound CP(O)(=O)OC(C(O)=O)CCCCCCC(O)=O BXFKTMFVBIKVQW-UHFFFAOYSA-N 0.000 claims description 5
NFIJHEPSTLSWFT-UHFFFAOYSA-N 2-[hydroxy(naphthalen-1-ylmethyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC2=CC=CC=C2C=1CP(O)(=O)OC(C(=O)O)C1=CC=CC=C1 NFIJHEPSTLSWFT-UHFFFAOYSA-N 0.000 claims description 5
DPAWETILEHQLSY-UHFFFAOYSA-N 2-[hydroxy(oxolan-2-yl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)C1CCCO1 DPAWETILEHQLSY-UHFFFAOYSA-N 0.000 claims description 5
MDZVCNVLIQJDKP-UHFFFAOYSA-N 2-[hydroxy(phenyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)C1=CC=CC=C1 MDZVCNVLIQJDKP-UHFFFAOYSA-N 0.000 claims description 5
NDWBFMWVGMHFGY-UHFFFAOYSA-N 2-[hydroxy(pyridin-2-yl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)C1=CC=CC=N1 NDWBFMWVGMHFGY-UHFFFAOYSA-N 0.000 claims description 5
QQTYYRHJTMVVOF-UHFFFAOYSA-N 2-[hydroxy(pyridin-3-yl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)C1=CC=CN=C1 QQTYYRHJTMVVOF-UHFFFAOYSA-N 0.000 claims description 5
JCEJKTQBBFCHIE-UHFFFAOYSA-N 2-[hydroxy(pyridin-4-yl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)C1=CC=NC=C1 JCEJKTQBBFCHIE-UHFFFAOYSA-N 0.000 claims description 5
MTCXOAOSPWQRJF-UHFFFAOYSA-N 2-[hydroxy(pyridin-4-yl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)C1=CC=NC=C1 MTCXOAOSPWQRJF-UHFFFAOYSA-N 0.000 claims description 5
ZPRKODXMIXWYNR-UHFFFAOYSA-N 2-[hydroxy(pyridin-4-ylmethyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CC1=CC=NC=C1 ZPRKODXMIXWYNR-UHFFFAOYSA-N 0.000 claims description 5
LMFHQMMDMHTRKH-UHFFFAOYSA-N 2-[hydroxy-[2-(oxolan-2-yl)ethyl]phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CCC1CCCO1 LMFHQMMDMHTRKH-UHFFFAOYSA-N 0.000 claims description 5
FPWQIHZKSDTHQR-UHFFFAOYSA-N 2-[hydroxy-[2-(oxolan-2-yl)ethyl]phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CCC1CCCO1 FPWQIHZKSDTHQR-UHFFFAOYSA-N 0.000 claims description 5
MUJCAQNLCPSNCT-UHFFFAOYSA-N 2-[hydroxy-[methoxy(phenyl)methyl]phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)C(OC)C1=CC=CC=C1 MUJCAQNLCPSNCT-UHFFFAOYSA-N 0.000 claims description 5
RRJIJCKXOJOADA-UHFFFAOYSA-N 3-[[hydroxy(thiophen-3-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CC(CC(O)=O)NP(O)(=O)CC=1C=CSC=1 RRJIJCKXOJOADA-UHFFFAOYSA-N 0.000 claims description 5
VBNINQANAUPRQX-UHFFFAOYSA-N 3-[hydroxy(1h-indol-4-ylmethyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=2NC=CC=2C=1CP(O)(=O)CC(C(=O)O)C1=CC=CC=C1 VBNINQANAUPRQX-UHFFFAOYSA-N 0.000 claims description 5
UBAPLCALYPQGAC-UHFFFAOYSA-N 3-[hydroxy(2-pyridin-3-ylethyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CCC1=CC=CN=C1 UBAPLCALYPQGAC-UHFFFAOYSA-N 0.000 claims description 5
OWOOESKBTYTALA-UHFFFAOYSA-N 3-[hydroxy(naphthalen-1-ylmethyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1CP(O)(=O)CC(C(=O)O)C1=CC=CC=C1 OWOOESKBTYTALA-UHFFFAOYSA-N 0.000 claims description 5
TXZFTXVTRAESKJ-UHFFFAOYSA-N 3-[hydroxy(pyridin-2-ylmethyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CC1=CC=CC=N1 TXZFTXVTRAESKJ-UHFFFAOYSA-N 0.000 claims description 5
IXEARQOIMYBMJD-UHFFFAOYSA-N 3-[hydroxy(pyridin-3-ylmethyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CC1=CC=CN=C1 IXEARQOIMYBMJD-UHFFFAOYSA-N 0.000 claims description 5
ZDNLLCAWQMWRPY-UHFFFAOYSA-N 3-[hydroxy(pyridin-4-ylmethyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CC1=CC=NC=C1 ZDNLLCAWQMWRPY-UHFFFAOYSA-N 0.000 claims description 5
TVEBXHHAUWOQCY-UHFFFAOYSA-N 3-[hydroxy(thiophen-2-ylmethyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CC1=CC=CS1 TVEBXHHAUWOQCY-UHFFFAOYSA-N 0.000 claims description 5
SKSVFCRDMGPIEH-UHFFFAOYSA-N 3-[hydroxy-[2-(1h-indol-3-yl)ethyl]phosphoryl]-2-phenylpropanoic acid Chemical compound C=1NC2=CC=CC=C2C=1CCP(O)(=O)CC(C(=O)O)C1=CC=CC=C1 SKSVFCRDMGPIEH-UHFFFAOYSA-N 0.000 claims description 5
125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 5
208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 5
206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 5
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 5
206010009944 Colon cancer Diseases 0.000 claims description 5
208000001333 Colorectal Neoplasms Diseases 0.000 claims description 5
208000033776 Myeloid Acute Leukemia Diseases 0.000 claims description 5
206010029260 Neuroblastoma Diseases 0.000 claims description 5
208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 5
208000031673 T-Cell Cutaneous Lymphoma Diseases 0.000 claims description 5
208000002495 Uterine Neoplasms Diseases 0.000 claims description 5
208000004354 Vulvar Neoplasms Diseases 0.000 claims description 5
201000007241 cutaneous T cell lymphoma Diseases 0.000 claims description 5
201000009277 hairy cell leukemia Diseases 0.000 claims description 5
208000014829 head and neck neoplasm Diseases 0.000 claims description 5
201000001441 melanoma Diseases 0.000 claims description 5
201000005962 mycosis fungoides Diseases 0.000 claims description 5
208000025638 primary cutaneous T-cell non-Hodgkin lymphoma Diseases 0.000 claims description 5
206010046766 uterine cancer Diseases 0.000 claims description 5
YHLLTSPCFWSURM-UHFFFAOYSA-N 2-[[ethyl(hydroxy)phosphoryl]amino]-2-phenylacetic acid Chemical compound CCP(O)(=O)NC(C(O)=O)C1=CC=CC=C1 YHLLTSPCFWSURM-UHFFFAOYSA-N 0.000 claims description 4
WVMWWUOUTKZOJK-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-2-yl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2NC(P(O)(=O)NC(CCC(=O)O)C(O)=O)=CC2=C1 WVMWWUOUTKZOJK-UHFFFAOYSA-N 0.000 claims description 4
KPXOWFMSSCTWNA-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-2-ylmethyl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=C2NC(CP(O)(=O)CC(CCC(=O)O)C(O)=O)=CC2=C1 KPXOWFMSSCTWNA-UHFFFAOYSA-N 0.000 claims description 4
IABYUVDXGCABGD-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-4-yl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C1=CC=CC2=C1C=CN2 IABYUVDXGCABGD-UHFFFAOYSA-N 0.000 claims description 4
BQUAJUHWMGFLGM-UHFFFAOYSA-N 2-[[hydroxy(2-naphthalen-2-ylethyl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=CC2=CC(CCP(O)(=O)CC(CCC(=O)O)C(O)=O)=CC=C21 BQUAJUHWMGFLGM-UHFFFAOYSA-N 0.000 claims description 4
NRIVWGXGGXINEJ-UHFFFAOYSA-N 2-[[hydroxy(naphthalen-1-yl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC2=CC=CC=C2C=1P(O)(=O)NC(C(=O)O)C1=CC=CC=C1 NRIVWGXGGXINEJ-UHFFFAOYSA-N 0.000 claims description 4
XQAKSYLUPBGJRA-UHFFFAOYSA-N 2-[[hydroxy(naphthalen-1-ylmethyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC2=CC=CC=C2C=1CP(O)(=O)NC(C(=O)O)C1=CC=CC=C1 XQAKSYLUPBGJRA-UHFFFAOYSA-N 0.000 claims description 4
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 description 4
WCAFPIFRHUAZQC-UHFFFAOYSA-N 2-[[hydroxy-[2-(oxolan-2-yl)ethyl]phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CCC1CCCO1 WCAFPIFRHUAZQC-UHFFFAOYSA-N 0.000 claims description 4
XQSSDRFVBZVILF-UHFFFAOYSA-N 2-[hydroxy(2-naphthalen-1-ylethyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC2=CC=CC=C2C=1CCP(O)(=O)OC(C(=O)O)C1=CC=CC=C1 XQSSDRFVBZVILF-UHFFFAOYSA-N 0.000 claims description 4
HVMZEIJOZRCFIZ-UHFFFAOYSA-N 2-[hydroxy(oxolan-2-yl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)C1CCCO1 HVMZEIJOZRCFIZ-UHFFFAOYSA-N 0.000 claims description 4
HWXBTNAVRSUOJR-UHFFFAOYSA-N 2-hydroxyglutaric acid Chemical compound OC(=O)C(O)CCC(O)=O HWXBTNAVRSUOJR-UHFFFAOYSA-N 0.000 claims description 4
PPOPJMKWKJQJHR-UHFFFAOYSA-N 3-[[hydroxy(1h-indol-3-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2C(CP(O)(=O)NC(CC(O)=O)CC(=O)O)=CNC2=C1 PPOPJMKWKJQJHR-UHFFFAOYSA-N 0.000 claims description 4
CAXAPLDWFXHPBK-UHFFFAOYSA-N 3-[[hydroxy(2-pyridin-3-ylethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CC(CC(O)=O)NP(O)(=O)CCC1=CC=CN=C1 CAXAPLDWFXHPBK-UHFFFAOYSA-N 0.000 claims description 4
YELSEQBMKCUMRH-UHFFFAOYSA-N 3-[[hydroxy(thiophen-2-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CC(CC(O)=O)NP(O)(=O)CC1=CC=CS1 YELSEQBMKCUMRH-UHFFFAOYSA-N 0.000 claims description 4
AMGNNFKCZQICJC-UHFFFAOYSA-N 3-[[hydroxy-[2-(1h-indol-3-yl)ethyl]phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2C(CCP(O)(=O)NC(CC(O)=O)CC(=O)O)=CNC2=C1 AMGNNFKCZQICJC-UHFFFAOYSA-N 0.000 claims description 4
CTJAHTYVENJGPA-UHFFFAOYSA-N 3-[hydroxy(naphthalen-1-yl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1P(O)(=O)CC(C(=O)O)C1=CC=CC=C1 CTJAHTYVENJGPA-UHFFFAOYSA-N 0.000 claims description 4
OIPIZEWHFPQKLC-UHFFFAOYSA-N 3-[hydroxy(naphthalen-2-ylmethyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1CP(O)(=O)CC(C(=O)O)C1=CC=CC=C1 OIPIZEWHFPQKLC-UHFFFAOYSA-N 0.000 claims description 4
206010006187 Breast cancer Diseases 0.000 claims description 4
208000026310 Breast neoplasm Diseases 0.000 claims description 4
206010027406 Mesothelioma Diseases 0.000 claims description 4
208000015914 Non-Hodgkin lymphomas 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
210000004404 adrenal cortex Anatomy 0.000 claims description 4
208000035475 disorder Diseases 0.000 claims description 4
BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 claims description 4
CULHXRDATVRQLL-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-3-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2C(CP(O)(=O)NC(CCC(=O)O)C(O)=O)=CNC2=C1 CULHXRDATVRQLL-UHFFFAOYSA-N 0.000 claims description 3
KKGRMLVZAYWZTC-UHFFFAOYSA-N 2-[[hydroxy(pyridin-2-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1=CC=CC=N1 KKGRMLVZAYWZTC-UHFFFAOYSA-N 0.000 claims description 3
YOCDHMICSMSLTQ-UHFFFAOYSA-N 2-[[hydroxy(pyridin-4-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1=CC=NC=C1 YOCDHMICSMSLTQ-UHFFFAOYSA-N 0.000 claims description 3
ATRMMLHYJBEYNP-UHFFFAOYSA-N 2-[[hydroxy-[2-(oxolan-2-yl)ethyl]phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CCC1CCCO1 ATRMMLHYJBEYNP-UHFFFAOYSA-N 0.000 claims description 3
FZRPXGNCHKMHTO-UHFFFAOYSA-N 3-[[hydroxy(2-thiophen-3-ylethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CC(CC(O)=O)NP(O)(=O)CCC=1C=CSC=1 FZRPXGNCHKMHTO-UHFFFAOYSA-N 0.000 claims description 3
YNVAMBSOBURVRN-UHFFFAOYSA-N 3-[[hydroxy(oxolan-2-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CC(CC(O)=O)NP(O)(=O)CC1CCCO1 YNVAMBSOBURVRN-UHFFFAOYSA-N 0.000 claims description 3
PTAKJAAFQJRBDF-UHFFFAOYSA-N 3-[[hydroxy(pyridin-2-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CC(CC(O)=O)NP(O)(=O)CC1=CC=CC=N1 PTAKJAAFQJRBDF-UHFFFAOYSA-N 0.000 claims description 3
RSRGOFOJJDTOJN-UHFFFAOYSA-N 3-[[hydroxy(pyridin-3-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CC(CC(O)=O)NP(O)(=O)CC1=CC=CN=C1 RSRGOFOJJDTOJN-UHFFFAOYSA-N 0.000 claims description 3
QDILTKOIJTVECG-UHFFFAOYSA-N 3-[[hydroxy-[2-(oxolan-2-yl)ethyl]phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CC(CC(O)=O)NP(O)(=O)CCC1CCCO1 QDILTKOIJTVECG-UHFFFAOYSA-N 0.000 claims description 3
206010025538 Malignant ascites Diseases 0.000 claims description 3
208000032271 Malignant tumor of penis Diseases 0.000 claims description 3
201000010536 head and neck cancer Diseases 0.000 claims description 3
206010041823 squamous cell carcinoma Diseases 0.000 claims description 3
206010046885 vaginal cancer Diseases 0.000 claims description 3
ZQSXMDJCWKAJFZ-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-2-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2NC(CP(O)(=O)NC(CCC(=O)O)C(O)=O)=CC2=C1 ZQSXMDJCWKAJFZ-UHFFFAOYSA-N 0.000 claims description 2
LJMHTTUCPUTRMK-UHFFFAOYSA-N 2-[[hydroxy(1h-indol-4-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1=CC=CC2=C1C=CN2 LJMHTTUCPUTRMK-UHFFFAOYSA-N 0.000 claims description 2
LQDCQAGCPHGVBY-UHFFFAOYSA-N 2-[[hydroxy(2-pyridin-3-ylethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CCC1=CC=CN=C1 LQDCQAGCPHGVBY-UHFFFAOYSA-N 0.000 claims description 2
YBACOWWKHIWWNI-UHFFFAOYSA-N 2-[[hydroxy(2-thiophen-3-ylethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CCC=1C=CSC=1 YBACOWWKHIWWNI-UHFFFAOYSA-N 0.000 claims description 2
SOMPNJZYFUDHBP-UHFFFAOYSA-N 2-[[hydroxy(oxolan-2-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1CCCO1 SOMPNJZYFUDHBP-UHFFFAOYSA-N 0.000 claims description 2
HHXIKNDUYNZTHH-UHFFFAOYSA-N 2-[[hydroxy(pyridin-3-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1=CC=CN=C1 HHXIKNDUYNZTHH-UHFFFAOYSA-N 0.000 claims description 2
AWUUZLLREKFWRC-UHFFFAOYSA-N 2-[[hydroxy(thiophen-2-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1=CC=CS1 AWUUZLLREKFWRC-UHFFFAOYSA-N 0.000 claims description 2
GIPIVXPOTQBUPZ-UHFFFAOYSA-N 3-[[hydroxy(1h-indol-4-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CC(CC(O)=O)NP(O)(=O)CC1=CC=CC2=C1C=CN2 GIPIVXPOTQBUPZ-UHFFFAOYSA-N 0.000 claims description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
241000282472 Canis lupus familiaris Species 0.000 claims description 2
229960000250 adipic acid Drugs 0.000 claims description 2
235000011037 adipic acid Nutrition 0.000 claims description 2
102000003958 Glutamate Carboxypeptidase II Human genes 0.000 claims 44
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 39
CIHIKAFYKFFIMC-UHFFFAOYSA-N OC(CCC(C(O)=O)NP(OCC1=CC=CC=C1)=O)=O Chemical compound OC(CCC(C(O)=O)NP(OCC1=CC=CC=C1)=O)=O CIHIKAFYKFFIMC-UHFFFAOYSA-N 0.000 claims 9
QRJFPEYYNVIDFL-UHFFFAOYSA-N OC(CCC(C(O)=O)OP(OCC1=CC=CC=C1)=O)=O Chemical compound OC(CCC(C(O)=O)OP(OCC1=CC=CC=C1)=O)=O QRJFPEYYNVIDFL-UHFFFAOYSA-N 0.000 claims 9
HEEHTCBCCSGAAM-UHFFFAOYSA-N OC(CCC(CP(OCC1=CC=CC=C1)=O)C(O)=O)=O Chemical compound OC(CCC(CP(OCC1=CC=CC=C1)=O)C(O)=O)=O HEEHTCBCCSGAAM-UHFFFAOYSA-N 0.000 claims 9
OCDJYTYVJFJMPF-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)CC(C(=O)O)CCCC(=O)O Chemical compound C(C1=CC=CC=C1)OP(=O)CC(C(=O)O)CCCC(=O)O OCDJYTYVJFJMPF-UHFFFAOYSA-N 0.000 claims 6
ROBJACCHTQQKTL-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)OC(C(=O)O)CCCC(=O)O Chemical compound C(C1=CC=CC=C1)OP(=O)OC(C(=O)O)CCCC(=O)O ROBJACCHTQQKTL-UHFFFAOYSA-N 0.000 claims 6
JZNXRMQVDQPULI-UHFFFAOYSA-N CC(C(O)=O)(C1=CSC=C1)NP(OCC1=CC=CC=C1)=O Chemical compound CC(C(O)=O)(C1=CSC=C1)NP(OCC1=CC=CC=C1)=O JZNXRMQVDQPULI-UHFFFAOYSA-N 0.000 claims 6
HNVIGHUIAXUPIX-UHFFFAOYSA-N CCCCOP(CC(CCC(O)=O)C(O)=O)=O Chemical compound CCCCOP(CC(CCC(O)=O)C(O)=O)=O HNVIGHUIAXUPIX-UHFFFAOYSA-N 0.000 claims 6
LKPRPYWMNKVCQF-UHFFFAOYSA-N CCCCOP(NC(CCC(O)=O)C(O)=O)=O Chemical compound CCCCOP(NC(CCC(O)=O)C(O)=O)=O LKPRPYWMNKVCQF-UHFFFAOYSA-N 0.000 claims 6
GHWADMORDIRRIA-UHFFFAOYSA-N CCCCOP(OC(CCC(O)=O)C(O)=O)=O Chemical compound CCCCOP(OC(CCC(O)=O)C(O)=O)=O GHWADMORDIRRIA-UHFFFAOYSA-N 0.000 claims 6
UUXOTVYMPRNOCS-UHFFFAOYSA-N OC(=O)CCC(C(O)=O)CP(=O)OCCC1=CC=CC=C1 Chemical compound OC(=O)CCC(C(O)=O)CP(=O)OCCC1=CC=CC=C1 UUXOTVYMPRNOCS-UHFFFAOYSA-N 0.000 claims 6
JMRQQTLHJIOFOO-UHFFFAOYSA-N OC(=O)CCC(C(O)=O)CP(=O)OCCCC1=CC=CC=C1 Chemical compound OC(=O)CCC(C(O)=O)CP(=O)OCCCC1=CC=CC=C1 JMRQQTLHJIOFOO-UHFFFAOYSA-N 0.000 claims 6
ODYQMIBONVWRNS-UHFFFAOYSA-N OC(C(C1=CSC=C1)NP(OCC1=CC=CC=C1)=O)=O Chemical compound OC(C(C1=CSC=C1)NP(OCC1=CC=CC=C1)=O)=O ODYQMIBONVWRNS-UHFFFAOYSA-N 0.000 claims 6
OZQLGOKAVBVHKA-UHFFFAOYSA-N OC(CCC(C(O)=O)OP(OC1=CC=CC=C1)=O)=O Chemical compound OC(CCC(C(O)=O)OP(OC1=CC=CC=C1)=O)=O OZQLGOKAVBVHKA-UHFFFAOYSA-N 0.000 claims 6
229910052736 halogen Inorganic materials 0.000 claims 6
150000002367 halogens Chemical class 0.000 claims 6
125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 5
AKSNVGMVNSZSLI-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)C1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)C1=CC=CC=C1 AKSNVGMVNSZSLI-UHFFFAOYSA-N 0.000 claims 5
ZCHARWAUCRCLGR-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)CCCC(=O)O Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)CCCC(=O)O ZCHARWAUCRCLGR-UHFFFAOYSA-N 0.000 claims 5
JMNIYDLOKANUAH-UHFFFAOYSA-N OC(CCC(C(O)=O)OP(OCCC1=CC=CC=C1)=O)=O Chemical compound OC(CCC(C(O)=O)OP(OCCC1=CC=CC=C1)=O)=O JMNIYDLOKANUAH-UHFFFAOYSA-N 0.000 claims 5
QGUYQUSNEQZSHU-UHFFFAOYSA-N OC(CCC(C(O)=O)OP(OCCCC1=CC=CC=C1)=O)=O Chemical compound OC(CCC(C(O)=O)OP(OCCCC1=CC=CC=C1)=O)=O QGUYQUSNEQZSHU-UHFFFAOYSA-N 0.000 claims 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 5
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims 3
NAJJMMSAHFDQAU-UHFFFAOYSA-N 2-[[hydroxy(pyridin-3-ylmethyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CC1=CC=CN=C1 NAJJMMSAHFDQAU-UHFFFAOYSA-N 0.000 claims 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
KVCMOIIQIVTMAQ-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)CC(C(=O)O)(C1=CC2=CC=CC=C2C=C1)C Chemical compound C(C1=CC=CC=C1)OP(=O)CC(C(=O)O)(C1=CC2=CC=CC=C2C=C1)C KVCMOIIQIVTMAQ-UHFFFAOYSA-N 0.000 claims 3
AZNMVNCRRMIAGD-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)CC(C(=O)O)(C1=CC=NC=C1)C Chemical compound C(C1=CC=CC=C1)OP(=O)CC(C(=O)O)(C1=CC=NC=C1)C AZNMVNCRRMIAGD-UHFFFAOYSA-N 0.000 claims 3
JAHAFRSAVZSUQR-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)CC(C(=O)O)C1=C2C=CNC2=CC=C1 Chemical compound C(C1=CC=CC=C1)OP(=O)CC(C(=O)O)C1=C2C=CNC2=CC=C1 JAHAFRSAVZSUQR-UHFFFAOYSA-N 0.000 claims 3
SHGALKBBEBIRGT-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)CC(C(=O)O)CC1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)OP(=O)CC(C(=O)O)CC1=CC=CC=C1 SHGALKBBEBIRGT-UHFFFAOYSA-N 0.000 claims 3
YTHRBPUOSYBGGG-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)CC(C(=O)O)CCCCCCC(=O)O Chemical compound C(C1=CC=CC=C1)OP(=O)CC(C(=O)O)CCCCCCC(=O)O YTHRBPUOSYBGGG-UHFFFAOYSA-N 0.000 claims 3
SJIXVIOTRBVHMB-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)CC(C(=O)O)CCCCCCCC(=O)O Chemical compound C(C1=CC=CC=C1)OP(=O)CC(C(=O)O)CCCCCCCC(=O)O SJIXVIOTRBVHMB-UHFFFAOYSA-N 0.000 claims 3
QNWOAAPBPWDKQU-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)(C1=CC2=CC=CC=C2C=C1)C Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)(C1=CC2=CC=CC=C2C=C1)C QNWOAAPBPWDKQU-UHFFFAOYSA-N 0.000 claims 3
KVWGCBBMCADEPG-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)(C1=NC=CC=C1)C Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)(C1=NC=CC=C1)C KVWGCBBMCADEPG-UHFFFAOYSA-N 0.000 claims 3
AGIWTSIYJAEDTP-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)(C1OCCC1)C Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)(C1OCCC1)C AGIWTSIYJAEDTP-UHFFFAOYSA-N 0.000 claims 3
VSYKQIKGSQUCQE-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)(C=1C=NC=CC1)C Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)(C=1C=NC=CC1)C VSYKQIKGSQUCQE-UHFFFAOYSA-N 0.000 claims 3
GZZKPLQREMVKJG-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)(C=1NC2=CC=CC=C2C1)C Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)(C=1NC2=CC=CC=C2C1)C GZZKPLQREMVKJG-UHFFFAOYSA-N 0.000 claims 3
PREDYHATIKIEJZ-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)(C=1SC=CC1)C Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)(C=1SC=CC1)C PREDYHATIKIEJZ-UHFFFAOYSA-N 0.000 claims 3
LFBBCTPMRPNHKZ-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)C Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)C LFBBCTPMRPNHKZ-UHFFFAOYSA-N 0.000 claims 3
UEUVRHYVVKBEAF-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)C1=CC=CC2=CC=CC=C12 Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)C1=CC=CC2=CC=CC=C12 UEUVRHYVVKBEAF-UHFFFAOYSA-N 0.000 claims 3
DEOWDSNZPCJRTI-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)C1CCCCC1 Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)C1CCCCC1 DEOWDSNZPCJRTI-UHFFFAOYSA-N 0.000 claims 3
IOKDRBCBQXONNI-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)CC Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)CC IOKDRBCBQXONNI-UHFFFAOYSA-N 0.000 claims 3
SFFSATPMABVOJZ-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)CC1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)CC1=CC=CC=C1 SFFSATPMABVOJZ-UHFFFAOYSA-N 0.000 claims 3
ZZEZHDHZWFDEIO-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)CCC Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)CCC ZZEZHDHZWFDEIO-UHFFFAOYSA-N 0.000 claims 3
YEFIAINGUSDZOW-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)CCCC Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)CCCC YEFIAINGUSDZOW-UHFFFAOYSA-N 0.000 claims 3
RWXACIHDSBXYJB-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)CCCCC(=O)O Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)CCCCC(=O)O RWXACIHDSBXYJB-UHFFFAOYSA-N 0.000 claims 3
IMKKAJWSPPJYIH-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)CCCCCCC(=O)O Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)CCCCCCC(=O)O IMKKAJWSPPJYIH-UHFFFAOYSA-N 0.000 claims 3
AJFHHLWTIHOCHJ-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)CCCCCCCC(=O)O Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)CCCCCCCC(=O)O AJFHHLWTIHOCHJ-UHFFFAOYSA-N 0.000 claims 3
MAANURNWIDLSCH-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(CCC(=O)O)(C)C1=CC2=CC=CC=C2C=C1 Chemical compound C(C1=CC=CC=C1)OP(=O)NC(CCC(=O)O)(C)C1=CC2=CC=CC=C2C=C1 MAANURNWIDLSCH-UHFFFAOYSA-N 0.000 claims 3
ZJJUTZCCRRRQKQ-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(CCC(=O)O)(C)C1=CNC2=CC=CC=C12 Chemical compound C(C1=CC=CC=C1)OP(=O)NC(CCC(=O)O)(C)C1=CNC2=CC=CC=C12 ZJJUTZCCRRRQKQ-UHFFFAOYSA-N 0.000 claims 3
IBNPDJZSKBPDKT-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(CCC(=O)O)(C)C=1C=NC=CC1 Chemical compound C(C1=CC=CC=C1)OP(=O)NC(CCC(=O)O)(C)C=1C=NC=CC1 IBNPDJZSKBPDKT-UHFFFAOYSA-N 0.000 claims 3
DDUPCJWIGLLPIR-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(CCC(=O)O)(CC)C1=CC2=CC=CC=C2C=C1 Chemical compound C(C1=CC=CC=C1)OP(=O)NC(CCC(=O)O)(CC)C1=CC2=CC=CC=C2C=C1 DDUPCJWIGLLPIR-UHFFFAOYSA-N 0.000 claims 3
ASRLWQWIZDAPKA-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(CCC(=O)O)C1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)OP(=O)NC(CCC(=O)O)C1=CC=CC=C1 ASRLWQWIZDAPKA-UHFFFAOYSA-N 0.000 claims 3
YEXWFWDOCBBBFL-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(CCC(=O)O)C1=CNC2=CC=CC=C12 Chemical compound C(C1=CC=CC=C1)OP(=O)NC(CCC(=O)O)C1=CNC2=CC=CC=C12 YEXWFWDOCBBBFL-UHFFFAOYSA-N 0.000 claims 3
NXJXTXDYWWTSED-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)OC(C(=O)O)CCCCC(=O)O Chemical compound C(C1=CC=CC=C1)OP(=O)OC(C(=O)O)CCCCC(=O)O NXJXTXDYWWTSED-UHFFFAOYSA-N 0.000 claims 3
VFAHRDWEFICDPB-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)OC(C(=O)O)CCCCCCCC(=O)O Chemical compound C(C1=CC=CC=C1)OP(=O)OC(C(=O)O)CCCCCCCC(=O)O VFAHRDWEFICDPB-UHFFFAOYSA-N 0.000 claims 3
KPDKNKJDLAWCGV-UHFFFAOYSA-N C(CCC)OP(=O)CC(C(=O)O)C1=CC=CC=C1 Chemical compound C(CCC)OP(=O)CC(C(=O)O)C1=CC=CC=C1 KPDKNKJDLAWCGV-UHFFFAOYSA-N 0.000 claims 3
DEXHACMFECHEGT-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)CCCCOP(=O)CC(C(=O)O)CCC(=O)O Chemical compound C1(=CC=CC2=CC=CC=C12)CCCCOP(=O)CC(C(=O)O)CCC(=O)O DEXHACMFECHEGT-UHFFFAOYSA-N 0.000 claims 3
QRAMUBZDJFUDQI-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)CCCCOP(=O)OC(C(=O)O)CCC(=O)O Chemical compound C1(=CC=CC2=CC=CC=C12)CCCCOP(=O)OC(C(=O)O)CCC(=O)O QRAMUBZDJFUDQI-UHFFFAOYSA-N 0.000 claims 3
BZTVKQYTNNIFMI-UHFFFAOYSA-N C1(=CC=CC2=CC=CC=C12)CCCOP(=O)OC(C(=O)O)CCC(=O)O Chemical compound C1(=CC=CC2=CC=CC=C12)CCCOP(=O)OC(C(=O)O)CCC(=O)O BZTVKQYTNNIFMI-UHFFFAOYSA-N 0.000 claims 3
UJHSSYFPDKYNON-UHFFFAOYSA-N C1(=CC=CC=C1)CCCCOP(=O)NC(C(=O)O)CCC(=O)O Chemical compound C1(=CC=CC=C1)CCCCOP(=O)NC(C(=O)O)CCC(=O)O UJHSSYFPDKYNON-UHFFFAOYSA-N 0.000 claims 3
SSVQJJVAPBXZCN-UHFFFAOYSA-N C1(=CC=CC=C1)CCCCOP(=O)OC(C(=O)O)CCC(=O)O Chemical compound C1(=CC=CC=C1)CCCCOP(=O)OC(C(=O)O)CCC(=O)O SSVQJJVAPBXZCN-UHFFFAOYSA-N 0.000 claims 3
WMQYZSSALUCPFV-UHFFFAOYSA-N C1(=CC=CC=C1)CCOP(=O)NC(C(=O)O)CCC(=O)O Chemical compound C1(=CC=CC=C1)CCOP(=O)NC(C(=O)O)CCC(=O)O WMQYZSSALUCPFV-UHFFFAOYSA-N 0.000 claims 3
HBJFBVVDEGTHJT-UHFFFAOYSA-N C1(=CC=CC=C1)COP(=O)CC(C(=O)O)CCCCC(=O)O Chemical compound C1(=CC=CC=C1)COP(=O)CC(C(=O)O)CCCCC(=O)O HBJFBVVDEGTHJT-UHFFFAOYSA-N 0.000 claims 3
FZNOJTPAEIBGGU-UHFFFAOYSA-N C1(CCCCC1)OP(=O)CC(C(=O)O)CCC(=O)O Chemical compound C1(CCCCC1)OP(=O)CC(C(=O)O)CCC(=O)O FZNOJTPAEIBGGU-UHFFFAOYSA-N 0.000 claims 3
GFGMSHITBXHZNV-UHFFFAOYSA-N C1(CCCCC1)OP(=O)NC(C(=O)O)CCC(=O)O Chemical compound C1(CCCCC1)OP(=O)NC(C(=O)O)CCC(=O)O GFGMSHITBXHZNV-UHFFFAOYSA-N 0.000 claims 3
LZAFQUPRADHXRW-UHFFFAOYSA-N C1(CCCCC1)OP(=O)OC(C(=O)O)CCC(=O)O Chemical compound C1(CCCCC1)OP(=O)OC(C(=O)O)CCC(=O)O LZAFQUPRADHXRW-UHFFFAOYSA-N 0.000 claims 3
MQCQNEJCMALFTI-UHFFFAOYSA-N C1=C(C=CC2=CC=CC=C12)CCCCOP(=O)CC(C(=O)O)CCC(=O)O Chemical compound C1=C(C=CC2=CC=CC=C12)CCCCOP(=O)CC(C(=O)O)CCC(=O)O MQCQNEJCMALFTI-UHFFFAOYSA-N 0.000 claims 3
WZECRUXMGYXBRH-UHFFFAOYSA-N C1=C(C=CC2=CC=CC=C12)CCCCOP(=O)NC(C(=O)O)CCC(=O)O Chemical compound C1=C(C=CC2=CC=CC=C12)CCCCOP(=O)NC(C(=O)O)CCC(=O)O WZECRUXMGYXBRH-UHFFFAOYSA-N 0.000 claims 3
SKJQHWJSDKHCIU-UHFFFAOYSA-N C1=C(C=CC2=CC=CC=C12)CCCCOP(=O)OC(C(=O)O)CCC(=O)O Chemical compound C1=C(C=CC2=CC=CC=C12)CCCCOP(=O)OC(C(=O)O)CCC(=O)O SKJQHWJSDKHCIU-UHFFFAOYSA-N 0.000 claims 3
JPNZYGKKBXHVJS-UHFFFAOYSA-N C1=C(C=CC2=CC=CC=C12)CCCOP(=O)OC(C(=O)O)CCC(=O)O Chemical compound C1=C(C=CC2=CC=CC=C12)CCCOP(=O)OC(C(=O)O)CCC(=O)O JPNZYGKKBXHVJS-UHFFFAOYSA-N 0.000 claims 3
JFHKRSZDDUPDKX-UHFFFAOYSA-N CC(C(O)=O)(C1=C(C=CN2)C2=CC=C1)NP(OCC1=CC=CC=C1)=O Chemical compound CC(C(O)=O)(C1=C(C=CN2)C2=CC=C1)NP(OCC1=CC=CC=C1)=O JFHKRSZDDUPDKX-UHFFFAOYSA-N 0.000 claims 3
WBHCRLWDRLKEOA-UHFFFAOYSA-N COC1=C(C=CC(=C1OC)OC)OP(=O)OC(C(=O)O)CCC(=O)O Chemical compound COC1=C(C=CC(=C1OC)OC)OP(=O)OC(C(=O)O)CCC(=O)O WBHCRLWDRLKEOA-UHFFFAOYSA-N 0.000 claims 3
MITIOKCNUWOBLD-UHFFFAOYSA-N O1C(CCC1)CCCOP(=O)OC(C(=O)O)CCC(=O)O Chemical compound O1C(CCC1)CCCOP(=O)OC(C(=O)O)CCC(=O)O MITIOKCNUWOBLD-UHFFFAOYSA-N 0.000 claims 3
VOGDAOSSGAFYAB-UHFFFAOYSA-N OC(=O)CCC(C(O)=O)CP(=O)OCCCCC1=CC=CC=C1 Chemical compound OC(=O)CCC(C(O)=O)CP(=O)OCCCCC1=CC=CC=C1 VOGDAOSSGAFYAB-UHFFFAOYSA-N 0.000 claims 3
230000001771 impaired effect Effects 0.000 claims 3
230000036210 malignancy Effects 0.000 claims 3
VUPMEVYDLXTCSO-UHFFFAOYSA-N 3-[[hydroxy(1h-indol-2-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2NC(CP(O)(=O)NC(CC(O)=O)CC(=O)O)=CC2=C1 VUPMEVYDLXTCSO-UHFFFAOYSA-N 0.000 claims 2
FEFWQBNMURYKNX-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)CC(C(=O)O)C1=C(C(=C(C=C1)OC)OC)OC Chemical compound C(C1=CC=CC=C1)OP(=O)CC(C(=O)O)C1=C(C(=C(C=C1)OC)OC)OC FEFWQBNMURYKNX-UHFFFAOYSA-N 0.000 claims 2
QRLBCYXZFJWWKB-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)(C1=CC=NC=C1)C Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)(C1=CC=NC=C1)C QRLBCYXZFJWWKB-UHFFFAOYSA-N 0.000 claims 2
WALYWIMSBYMBPG-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)(C1=CNC2=CC=CC=C12)C Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)(C1=CNC2=CC=CC=C12)C WALYWIMSBYMBPG-UHFFFAOYSA-N 0.000 claims 2
SQTUJYYETJAULI-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)C1=C(C(=C(C=C1)OC)OC)OC Chemical compound C(C1=CC=CC=C1)OP(=O)NC(C(=O)O)C1=C(C(=C(C=C1)OC)OC)OC SQTUJYYETJAULI-UHFFFAOYSA-N 0.000 claims 2
QZRQYGGUHPGJQR-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)NC(CCC(=O)O)C=1C=NC=CC1 Chemical compound C(C1=CC=CC=C1)OP(=O)NC(CCC(=O)O)C=1C=NC=CC1 QZRQYGGUHPGJQR-UHFFFAOYSA-N 0.000 claims 2
ZUULBFSOKXAWDE-UHFFFAOYSA-N C(C1=CC=CC=C1)OP(=O)OC(CCC(=O)O)(CC)C1=CC2=CC=CC=C2C=C1 Chemical compound C(C1=CC=CC=C1)OP(=O)OC(CCC(=O)O)(CC)C1=CC2=CC=CC=C2C=C1 ZUULBFSOKXAWDE-UHFFFAOYSA-N 0.000 claims 2
201000008026 nephroblastoma Diseases 0.000 claims 2
201000005102 vulva cancer Diseases 0.000 claims 2
QYXNKTDNEWOBNH-UHFFFAOYSA-N 2-[[hydroxy-[2-(1h-indol-3-yl)ethyl]phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2C(CCP(O)(=O)NC(CCC(=O)O)C(O)=O)=CNC2=C1 QYXNKTDNEWOBNH-UHFFFAOYSA-N 0.000 claims 1
ZHQCSMCHLZTQNU-UHFFFAOYSA-N 2-methyl-2-thiophen-3-ylpropanoic acid Chemical compound OC(=O)C(C)(C)C=1C=CSC=1 ZHQCSMCHLZTQNU-UHFFFAOYSA-N 0.000 claims 1
OYWLHXWHKLWRLW-UHFFFAOYSA-N 2-pyridin-3-ylbutanoic acid Chemical compound CCC(C(O)=O)C1=CC=CN=C1 OYWLHXWHKLWRLW-UHFFFAOYSA-N 0.000 claims 1
LOYKAXQLDGPNKY-UHFFFAOYSA-N 3-[[hydroxy(pyridin-4-ylmethyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CC(CC(O)=O)NP(O)(=O)CC1=CC=NC=C1 LOYKAXQLDGPNKY-UHFFFAOYSA-N 0.000 claims 1
IDXILEBEPUJKER-UHFFFAOYSA-N COC1=CC=C(COP(=O)NC(C(=O)O)CCC(=O)O)C=C1 Chemical compound COC1=CC=C(COP(=O)NC(C(=O)O)CCC(=O)O)C=C1 IDXILEBEPUJKER-UHFFFAOYSA-N 0.000 claims 1
NORXXKOFYUEQBX-UHFFFAOYSA-N N1=C(C=CC=C1)OP(=O)OC(C(=O)O)CCC(=O)O Chemical compound N1=C(C=CC=C1)OP(=O)OC(C(=O)O)CCC(=O)O NORXXKOFYUEQBX-UHFFFAOYSA-N 0.000 claims 1
YHAWFSGHYCEBCK-UHFFFAOYSA-N N1=CC(=CC=C1)OP(=O)NC(C(=O)O)CCC(=O)O Chemical compound N1=CC(=CC=C1)OP(=O)NC(C(=O)O)CCC(=O)O YHAWFSGHYCEBCK-UHFFFAOYSA-N 0.000 claims 1
WXBJFWARLLOEOT-UHFFFAOYSA-N N1=CC=C(C=C1)OP(=O)OC(C(=O)O)CCC(=O)O Chemical compound N1=CC=C(C=C1)OP(=O)OC(C(=O)O)CCC(=O)O WXBJFWARLLOEOT-UHFFFAOYSA-N 0.000 claims 1
MEDOZJMLANMHNW-UHFFFAOYSA-N N1C(=CC2=CC=CC=C12)OP(=O)NC(C(=O)O)CCC(=O)O Chemical compound N1C(=CC2=CC=CC=C12)OP(=O)NC(C(=O)O)CCC(=O)O MEDOZJMLANMHNW-UHFFFAOYSA-N 0.000 claims 1
SXPJWNHHCNALAA-UHFFFAOYSA-N N1C=CC2=C(C=CC=C12)OP(=O)CC(C(=O)O)CCC(=O)O Chemical compound N1C=CC2=C(C=CC=C12)OP(=O)CC(C(=O)O)CCC(=O)O SXPJWNHHCNALAA-UHFFFAOYSA-N 0.000 claims 1
206010047741 Vulval cancer Diseases 0.000 claims 1
201000002454 adrenal cortex cancer Diseases 0.000 claims 1
210000000481 breast Anatomy 0.000 claims 1
210000000232 gallbladder Anatomy 0.000 claims 1
208000025854 malignant tumor of adrenal cortex Diseases 0.000 claims 1
230000005764 inhibitory process Effects 0.000 abstract description 10
102000004190 Enzymes Human genes 0.000 abstract description 9
108090000790 Enzymes Proteins 0.000 abstract description 9
230000012010 growth Effects 0.000 abstract description 7
230000002378 acidificating effect Effects 0.000 abstract description 4
150000008298 phosphoramidates Chemical class 0.000 abstract description 4
102000004860 Dipeptidases Human genes 0.000 abstract description 3
108090001081 Dipeptidases Proteins 0.000 abstract description 3
ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract description 3
229940127422 Dipeptidase Inhibitors Drugs 0.000 abstract 1
102100020995 Putative N-acetylated-alpha-linked acidic dipeptidase Human genes 0.000 description 112
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
206010061289 metastatic neoplasm Diseases 0.000 description 51
230000001394 metastastic effect Effects 0.000 description 49
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
230000000683 nonmetastatic effect Effects 0.000 description 41
235000019439 ethyl acetate Nutrition 0.000 description 37
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
239000007788 liquid Substances 0.000 description 21
OPVPGKGADVGKTG-BQBZGAKWSA-N Ac-Asp-Glu Chemical compound CC(=O)N[C@@H](CC(O)=O)C(=O)N[C@H](C(O)=O)CCC(O)=O OPVPGKGADVGKTG-BQBZGAKWSA-N 0.000 description 19
229930195712 glutamate Natural products 0.000 description 18
238000002360 preparation method Methods 0.000 description 18
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 17
229940079593 drug Drugs 0.000 description 17
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
238000001356 surgical procedure Methods 0.000 description 16
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 15
241000894007 species Species 0.000 description 15
241000700159 Rattus Species 0.000 description 14
239000003921 oil Substances 0.000 description 14
235000019198 oils Nutrition 0.000 description 14
GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 14
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 description 13
239000000725 suspension Substances 0.000 description 13
ASNFTDCKZKHJSW-REOHCLBHSA-N Quisqualic acid Chemical compound OC(=O)[C@@H](N)CN1OC(=O)NC1=O ASNFTDCKZKHJSW-REOHCLBHSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
ACXSUJZCYZEUIF-UHFFFAOYSA-N dibenzyl 2-methylidenepentanedioate Chemical compound C=1C=CC=CC=1COC(=O)C(=C)CCC(=O)OCC1=CC=CC=C1 ACXSUJZCYZEUIF-UHFFFAOYSA-N 0.000 description 12
125000000896 monocarboxylic acid group Chemical group 0.000 description 12
230000002829 reductive effect Effects 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
ZNWIUVIHLUVLTB-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 ZNWIUVIHLUVLTB-UHFFFAOYSA-N 0.000 description 11
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 description 11
241000699670 Mus sp. Species 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical class O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 description 11
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 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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 description 9
ASNFTDCKZKHJSW-UHFFFAOYSA-N DL-Quisqualic acid Natural products OC(=O)C(N)CN1OC(=O)NC1=O ASNFTDCKZKHJSW-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
102100041003 Glutamate carboxypeptidase 2 Human genes 0.000 description 9
101000892862 Homo sapiens Glutamate carboxypeptidase 2 Proteins 0.000 description 9
239000012044 organic layer Substances 0.000 description 9
230000005855 radiation Effects 0.000 description 9
JOZLXFLMUUQCRN-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CC1=CC=CC=C1 JOZLXFLMUUQCRN-UHFFFAOYSA-N 0.000 description 8
FTABEIRZLTZXBT-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-thiophen-3-ylacetic acid Chemical compound C1=CSC=C1C(C(=O)O)NP(O)(=O)CC1=CC=CC=C1 FTABEIRZLTZXBT-UHFFFAOYSA-N 0.000 description 8
YPBRRUMVNVJSQX-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-thiophen-3-ylpropanoic acid Chemical compound C1=CSC=C1C(C)(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 YPBRRUMVNVJSQX-UHFFFAOYSA-N 0.000 description 8
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 description 8
OXVBJVMKAPKLRB-UHFFFAOYSA-N 2-[[hydroxy(phenyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)C1=CC=CC=C1 OXVBJVMKAPKLRB-UHFFFAOYSA-N 0.000 description 8
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 description 8
VAWOQWLVEGONIX-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CC1=CC=CC=C1 VAWOQWLVEGONIX-UHFFFAOYSA-N 0.000 description 8
FVTWASYVAMBOJY-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-thiophen-3-ylacetic acid Chemical compound C1=CSC=C1C(C(=O)O)OP(O)(=O)CC1=CC=CC=C1 FVTWASYVAMBOJY-UHFFFAOYSA-N 0.000 description 8
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 description 8
WIUJSXHPUZCVOS-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CC1=CC=CC=C1 WIUJSXHPUZCVOS-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
239000002246 antineoplastic agent Substances 0.000 description 8
239000003795 chemical substances by application Substances 0.000 description 8
239000012230 colorless oil Substances 0.000 description 8
201000010099 disease Diseases 0.000 description 8
229940088598 enzyme Drugs 0.000 description 8
125000001475 halogen functional group Chemical group 0.000 description 8
238000000338 in vitro Methods 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
238000003756 stirring Methods 0.000 description 8
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 description 7
SVWHVKOIOWZDQX-UHFFFAOYSA-N 2-[[hydroxy(3-phenylpropyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CCCC1=CC=CC=C1 SVWHVKOIOWZDQX-UHFFFAOYSA-N 0.000 description 7
VNTSOPJXNJZGDI-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-thiophen-3-ylpropanoic acid Chemical compound C1=CSC=C1C(C)(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 VNTSOPJXNJZGDI-UHFFFAOYSA-N 0.000 description 7
108091003079 Bovine Serum Albumin Proteins 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
235000011054 acetic acid Nutrition 0.000 description 7
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 7
239000000706 filtrate Substances 0.000 description 7
238000003818 flash chromatography Methods 0.000 description 7
229910052763 palladium Inorganic materials 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
239000002002 slurry Substances 0.000 description 7
210000001519 tissue Anatomy 0.000 description 7
QIMHASXDVZXXRJ-UHFFFAOYSA-N 2-[[butyl(hydroxy)phosphoryl]amino]pentanedioic acid Chemical compound CCCCP(O)(=O)NC(C(O)=O)CCC(O)=O QIMHASXDVZXXRJ-UHFFFAOYSA-N 0.000 description 6
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 description 6
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 description 6
JCGFAKLXDGLFJU-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-methyl-2-thiophen-3-ylpropanoic acid Chemical compound C1=CSC=C1C(C)(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 JCGFAKLXDGLFJU-UHFFFAOYSA-N 0.000 description 6
GMDDMTLASANELO-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-thiophen-3-ylpropanoic acid Chemical compound C1=CSC=C1C(C(=O)O)CP(O)(=O)CC1=CC=CC=C1 GMDDMTLASANELO-UHFFFAOYSA-N 0.000 description 6
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
102000007066 Prostate-Specific Antigen Human genes 0.000 description 6
108010072866 Prostate-Specific Antigen Proteins 0.000 description 6
IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 6
208000009956 adenocarcinoma Diseases 0.000 description 6
229940127089 cytotoxic agent Drugs 0.000 description 6
208000037819 metastatic cancer Diseases 0.000 description 6
208000011575 metastatic malignant neoplasm Diseases 0.000 description 6
239000012299 nitrogen atmosphere Substances 0.000 description 6
230000003442 weekly effect Effects 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 5
206010027476 Metastases Diseases 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
235000019445 benzyl alcohol Nutrition 0.000 description 5
210000004556 brain Anatomy 0.000 description 5
239000012267 brine Substances 0.000 description 5
238000003745 diagnosis Methods 0.000 description 5
238000000921 elemental analysis Methods 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 5
239000010410 layer Substances 0.000 description 5
239000011159 matrix material Substances 0.000 description 5
238000005259 measurement Methods 0.000 description 5
230000009401 metastasis Effects 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
210000004881 tumor cell Anatomy 0.000 description 5
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 5
CUGBOAYBYONPAI-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-(1h-indol-2-yl)acetic acid Chemical compound C=1C2=CC=CC=C2NC=1C(C(=O)O)NP(O)(=O)CC1=CC=CC=C1 CUGBOAYBYONPAI-UHFFFAOYSA-N 0.000 description 4
PMZVXMMYEJFFNR-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-(1h-indol-2-yl)propanoic acid Chemical compound C=1C2=CC=CC=C2NC=1C(C)(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 PMZVXMMYEJFFNR-UHFFFAOYSA-N 0.000 description 4
SGXDTRJQNGDHLI-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-(1h-indol-3-yl)acetic acid Chemical compound C=1NC2=CC=CC=C2C=1C(C(=O)O)NP(O)(=O)CC1=CC=CC=C1 SGXDTRJQNGDHLI-UHFFFAOYSA-N 0.000 description 4
KCGKVDNSWJTPAR-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-(1h-indol-4-yl)acetic acid Chemical compound C=1C=CC=2NC=CC=2C=1C(C(=O)O)NP(O)(=O)CC1=CC=CC=C1 KCGKVDNSWJTPAR-UHFFFAOYSA-N 0.000 description 4
XBAQVHJMENOZNX-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-(1h-indol-4-yl)propanoic acid Chemical compound C=1C=CC=2NC=CC=2C=1C(C)(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 XBAQVHJMENOZNX-UHFFFAOYSA-N 0.000 description 4
RHFOVIRYIBCXTD-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-(oxolan-2-yl)acetic acid Chemical compound C1CCOC1C(C(=O)O)NP(O)(=O)CC1=CC=CC=C1 RHFOVIRYIBCXTD-UHFFFAOYSA-N 0.000 description 4
KLVKRAAHAJUTOS-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-cyclohexylacetic acid Chemical compound C1CCCCC1C(C(=O)O)NP(O)(=O)CC1=CC=CC=C1 KLVKRAAHAJUTOS-UHFFFAOYSA-N 0.000 description 4
NNYHJKCFVXTBEO-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-cyclohexylpropanoic acid Chemical compound C1CCCCC1C(C(O)=O)(C)NP(O)(=O)CC1=CC=CC=C1 NNYHJKCFVXTBEO-UHFFFAOYSA-N 0.000 description 4
CRGVYKVPJLVZET-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-naphthalen-1-ylacetic acid Chemical compound C=1C=CC2=CC=CC=C2C=1C(C(=O)O)NP(O)(=O)CC1=CC=CC=C1 CRGVYKVPJLVZET-UHFFFAOYSA-N 0.000 description 4
AMDQKMKVBXNSHH-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-naphthalen-2-ylacetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C(C(=O)O)NP(O)(=O)CC1=CC=CC=C1 AMDQKMKVBXNSHH-UHFFFAOYSA-N 0.000 description 4
ZMVLFSHMAVLUDX-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-naphthalen-2-ylpropanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C(C)(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 ZMVLFSHMAVLUDX-UHFFFAOYSA-N 0.000 description 4
XXOZVGKUQYKEGM-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-pyridin-2-ylacetic acid Chemical compound C=1C=CC=NC=1C(C(=O)O)NP(O)(=O)CC1=CC=CC=C1 XXOZVGKUQYKEGM-UHFFFAOYSA-N 0.000 description 4
FOWYNWNATJSQMK-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-pyridin-3-ylacetic acid Chemical compound C=1C=CN=CC=1C(C(=O)O)NP(O)(=O)CC1=CC=CC=C1 FOWYNWNATJSQMK-UHFFFAOYSA-N 0.000 description 4
BKVUPNMDVNFUTB-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-pyridin-3-ylpropanoic acid Chemical compound C=1C=CN=CC=1C(C)(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 BKVUPNMDVNFUTB-UHFFFAOYSA-N 0.000 description 4
PCZMOQCVVSXQFE-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-pyridin-4-ylacetic acid Chemical compound C=1C=NC=CC=1C(C(=O)O)NP(O)(=O)CC1=CC=CC=C1 PCZMOQCVVSXQFE-UHFFFAOYSA-N 0.000 description 4
BXIGCOGITDGZTK-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-pyridin-4-ylpropanoic acid Chemical compound C=1C=NC=CC=1C(C)(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 BXIGCOGITDGZTK-UHFFFAOYSA-N 0.000 description 4
OMBPBXBPWBPXJN-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-thiophen-2-ylacetic acid Chemical compound C=1C=CSC=1C(C(=O)O)NP(O)(=O)CC1=CC=CC=C1 OMBPBXBPWBPXJN-UHFFFAOYSA-N 0.000 description 4
RDOLZZKLIJULEX-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-thiophen-2-ylpropanoic acid Chemical compound C=1C=CSC=1C(C)(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 RDOLZZKLIJULEX-UHFFFAOYSA-N 0.000 description 4
QLYAXMJRWNPPMV-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-3-phenylpropanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)NC(C(=O)O)CC1=CC=CC=C1 QLYAXMJRWNPPMV-UHFFFAOYSA-N 0.000 description 4
ONFDYNIMZPDDPU-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]butanoic acid Chemical compound CCC(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 ONFDYNIMZPDDPU-UHFFFAOYSA-N 0.000 description 4
WEKICBVBMKNYAO-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]heptanedioic acid Chemical compound OC(=O)CCCCC(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 WEKICBVBMKNYAO-UHFFFAOYSA-N 0.000 description 4
KKILFMQLWJDQOA-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]hexanedioic acid Chemical compound OC(=O)CCCC(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 KKILFMQLWJDQOA-UHFFFAOYSA-N 0.000 description 4
JKHQXWYDYALDIK-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]nonanedioic acid Chemical compound OC(=O)CCCCCCC(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 JKHQXWYDYALDIK-UHFFFAOYSA-N 0.000 description 4
LZMCBFPUVVZFNJ-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]octanedioic acid Chemical compound OC(=O)CCCCCC(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 LZMCBFPUVVZFNJ-UHFFFAOYSA-N 0.000 description 4
NMEMJMPBHATIIG-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]pentanoic acid Chemical compound CCCC(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 NMEMJMPBHATIIG-UHFFFAOYSA-N 0.000 description 4
YUPQIKQTFVBFEO-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]propanoic acid Chemical compound OC(=O)C(C)NP(O)(=O)CC1=CC=CC=C1 YUPQIKQTFVBFEO-UHFFFAOYSA-N 0.000 description 4
RQMUHNDAKCQJGK-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]methyl]-3-pyridin-2-ylpropanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)CC(C(=O)O)CC1=CC=CC=N1 RQMUHNDAKCQJGK-UHFFFAOYSA-N 0.000 description 4
OWBADIZAWBSPRI-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]methyl]-4-(oxolan-2-yl)butanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)CC(C(=O)O)CCC1CCCO1 OWBADIZAWBSPRI-UHFFFAOYSA-N 0.000 description 4
QRBMANPOOLKTCQ-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]methyl]-4-naphthalen-1-ylbutanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1CCC(C(=O)O)CP(O)(=O)CC1=CC=CC=C1 QRBMANPOOLKTCQ-UHFFFAOYSA-N 0.000 description 4
FXKLKJWKHIDYTG-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]methyl]-4-naphthalen-2-ylbutanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1CCC(C(=O)O)CP(O)(=O)CC1=CC=CC=C1 FXKLKJWKHIDYTG-UHFFFAOYSA-N 0.000 description 4
IRAOSOZVIQOOKB-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]methyl]-4-phenylbutanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)CC(C(=O)O)CCC1=CC=CC=C1 IRAOSOZVIQOOKB-UHFFFAOYSA-N 0.000 description 4
QIKRFISWSOQHST-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]methyl]butanoic acid Chemical compound CCC(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 QIKRFISWSOQHST-UHFFFAOYSA-N 0.000 description 4
XMSIRJQSCRUXCZ-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]methyl]heptanedioic acid Chemical compound OC(=O)CCCCC(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 XMSIRJQSCRUXCZ-UHFFFAOYSA-N 0.000 description 4
XFROPECPXOQXGX-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]methyl]hexanedioic acid Chemical compound OC(=O)CCCC(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 XFROPECPXOQXGX-UHFFFAOYSA-N 0.000 description 4
HPIZIZDZVOBFOM-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]methyl]hexanoic acid Chemical compound CCCCC(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 HPIZIZDZVOBFOM-UHFFFAOYSA-N 0.000 description 4
XVFPUGHWBADATR-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]methyl]nonanedioic acid Chemical compound OC(=O)CCCCCCC(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 XVFPUGHWBADATR-UHFFFAOYSA-N 0.000 description 4
WLEAVBZLXCXFBG-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]methyl]octanedioic acid Chemical compound OC(=O)CCCCCC(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 WLEAVBZLXCXFBG-UHFFFAOYSA-N 0.000 description 4
GHMWBGXUNNDBCR-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]methyl]pentanoic acid Chemical compound CCCC(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 GHMWBGXUNNDBCR-UHFFFAOYSA-N 0.000 description 4
ISACNRUAIOKZFO-UHFFFAOYSA-N 2-[[butyl(hydroxy)phosphoryl]amino]-2-phenylacetic acid Chemical compound CCCCP(O)(=O)NC(C(O)=O)C1=CC=CC=C1 ISACNRUAIOKZFO-UHFFFAOYSA-N 0.000 description 4
QITIVUFBDNHDGJ-UHFFFAOYSA-N 2-[[cyclohexyl(hydroxy)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)C1CCCCC1 QITIVUFBDNHDGJ-UHFFFAOYSA-N 0.000 description 4
CYTLDFYLKHRWJO-UHFFFAOYSA-N 2-[[hydroxy(2-phenylethyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CCC1=CC=CC=C1 CYTLDFYLKHRWJO-UHFFFAOYSA-N 0.000 description 4
FFPAEASECFDNMZ-UHFFFAOYSA-N 2-[[hydroxy(3-naphthalen-1-ylpropyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2C(CCCP(O)(=O)NC(CCC(=O)O)C(O)=O)=CC=CC2=C1 FFPAEASECFDNMZ-UHFFFAOYSA-N 0.000 description 4
HGIZIMRGJKVTJS-UHFFFAOYSA-N 2-[[hydroxy(3-phenylprop-2-enyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CC=CC1=CC=CC=C1 HGIZIMRGJKVTJS-UHFFFAOYSA-N 0.000 description 4
BMAAZWSXAOZZHV-UHFFFAOYSA-N 2-[[hydroxy(4-naphthalen-1-ylbutyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2C(CCCCP(O)(=O)NC(CCC(=O)O)C(O)=O)=CC=CC2=C1 BMAAZWSXAOZZHV-UHFFFAOYSA-N 0.000 description 4
NVZPUWBDOOXWIL-UHFFFAOYSA-N 2-[[hydroxy(4-naphthalen-2-ylbutyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=CC2=CC(CCCCP(O)(=O)NC(CCC(=O)O)C(O)=O)=CC=C21 NVZPUWBDOOXWIL-UHFFFAOYSA-N 0.000 description 4
COBPGLALOTXCKU-UHFFFAOYSA-N 2-[[hydroxy(4-naphthalen-2-ylbutyl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=CC2=CC(CCCCP(O)(=O)CC(CCC(=O)O)C(O)=O)=CC=C21 COBPGLALOTXCKU-UHFFFAOYSA-N 0.000 description 4
MNNNCNOBWZGYQS-UHFFFAOYSA-N 2-[[hydroxy(4-phenylbutyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CCCCC1=CC=CC=C1 MNNNCNOBWZGYQS-UHFFFAOYSA-N 0.000 description 4
HHRXZMKKUJBCMK-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]amino]octanedioic acid Chemical compound CP(O)(=O)NC(C(O)=O)CCCCCC(O)=O HHRXZMKKUJBCMK-UHFFFAOYSA-N 0.000 description 4
HXOJTYYRXKNKER-UHFFFAOYSA-N 2-[[hydroxy(methyl)phosphoryl]methyl]octanedioic acid Chemical compound CP(O)(=O)CC(C(O)=O)CCCCCC(O)=O HXOJTYYRXKNKER-UHFFFAOYSA-N 0.000 description 4
WRXRNAQZRMPUGP-UHFFFAOYSA-N 2-[[hydroxy(phenyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)C1=CC=CC=C1 WRXRNAQZRMPUGP-UHFFFAOYSA-N 0.000 description 4
IKWYHDVSCUMYSM-UHFFFAOYSA-N 2-[[hydroxy(propyl)phosphoryl]methyl]pentanedioic acid Chemical compound CCCP(O)(=O)CC(C(O)=O)CCC(O)=O IKWYHDVSCUMYSM-UHFFFAOYSA-N 0.000 description 4
SQCZRPMGGNZNFF-UHFFFAOYSA-N 2-[[hydroxy-[3-(oxolan-2-yl)propyl]phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CCCC1CCCO1 SQCZRPMGGNZNFF-UHFFFAOYSA-N 0.000 description 4
JTDZZQTWHPEVCS-UHFFFAOYSA-N 2-[[hydroxy-[3-(oxolan-2-yl)propyl]phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CCCC1CCCO1 JTDZZQTWHPEVCS-UHFFFAOYSA-N 0.000 description 4
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 description 4
OBPXCJSPHIFDQM-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-(1h-indol-2-yl)acetic acid Chemical compound C=1C2=CC=CC=C2NC=1C(C(=O)O)OP(O)(=O)CC1=CC=CC=C1 OBPXCJSPHIFDQM-UHFFFAOYSA-N 0.000 description 4
JIEWTSOQEIEMAM-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-(1h-indol-3-yl)acetic acid Chemical compound C=1NC2=CC=CC=C2C=1C(C(=O)O)OP(O)(=O)CC1=CC=CC=C1 JIEWTSOQEIEMAM-UHFFFAOYSA-N 0.000 description 4
XERJQINOCMHXPZ-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-(1h-indol-4-yl)acetic acid Chemical compound C=1C=CC=2NC=CC=2C=1C(C(=O)O)OP(O)(=O)CC1=CC=CC=C1 XERJQINOCMHXPZ-UHFFFAOYSA-N 0.000 description 4
SDOKHDKLJFIQQF-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-(1h-indol-4-yl)propanoic acid Chemical compound C=1C=CC=2NC=CC=2C=1C(C)(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 SDOKHDKLJFIQQF-UHFFFAOYSA-N 0.000 description 4
UEWQWWUOLAUZKY-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-cyclohexylacetic acid Chemical compound C1CCCCC1C(C(=O)O)OP(O)(=O)CC1=CC=CC=C1 UEWQWWUOLAUZKY-UHFFFAOYSA-N 0.000 description 4
RPYIYHCDHNKNOB-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-naphthalen-1-ylacetic acid Chemical compound C=1C=CC2=CC=CC=C2C=1C(C(=O)O)OP(O)(=O)CC1=CC=CC=C1 RPYIYHCDHNKNOB-UHFFFAOYSA-N 0.000 description 4
TWFVXSKTIRFMCZ-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-naphthalen-1-ylpropanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1C(C)(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 TWFVXSKTIRFMCZ-UHFFFAOYSA-N 0.000 description 4
FAXQLRHBAPGLFB-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-pyridin-2-ylacetic acid Chemical compound C=1C=CC=NC=1C(C(=O)O)OP(O)(=O)CC1=CC=CC=C1 FAXQLRHBAPGLFB-UHFFFAOYSA-N 0.000 description 4
ICVYUOAIIRHOKS-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-pyridin-2-ylpropanoic acid Chemical compound C=1C=CC=NC=1C(C)(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 ICVYUOAIIRHOKS-UHFFFAOYSA-N 0.000 description 4
GIQNHDYUXHWEAX-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-pyridin-3-ylpropanoic acid Chemical compound C=1C=CN=CC=1C(C)(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 GIQNHDYUXHWEAX-UHFFFAOYSA-N 0.000 description 4
LWGVNEMLIGLVLS-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-pyridin-4-ylacetic acid Chemical compound C=1C=NC=CC=1C(C(=O)O)OP(O)(=O)CC1=CC=CC=C1 LWGVNEMLIGLVLS-UHFFFAOYSA-N 0.000 description 4
VZOOUMSPSMVYPI-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-pyridin-4-ylpropanoic acid Chemical compound C=1C=NC=CC=1C(C)(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 VZOOUMSPSMVYPI-UHFFFAOYSA-N 0.000 description 4
JKEGSMIRRKHVGB-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-thiophen-2-ylpropanoic acid Chemical compound C=1C=CSC=1C(C)(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 JKEGSMIRRKHVGB-UHFFFAOYSA-N 0.000 description 4
PJQYAAMJHRXFCP-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxydecanedioic acid Chemical compound OC(=O)CCCCCCCC(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 PJQYAAMJHRXFCP-UHFFFAOYSA-N 0.000 description 4
QJYWSMDSUVEYJT-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxyheptanedioic acid Chemical compound OC(=O)CCCCC(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 QJYWSMDSUVEYJT-UHFFFAOYSA-N 0.000 description 4
YHZIVTBAJGJOBG-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxynonanedioic acid Chemical compound OC(=O)CCCCCCC(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 YHZIVTBAJGJOBG-UHFFFAOYSA-N 0.000 description 4
WZDNYRLOZKMGJN-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxyoctanedioic acid Chemical compound OC(=O)CCCCCC(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 WZDNYRLOZKMGJN-UHFFFAOYSA-N 0.000 description 4
DKFSVCUCIVOVMY-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxypentanoic acid Chemical compound CCCC(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 DKFSVCUCIVOVMY-UHFFFAOYSA-N 0.000 description 4
PYGHZFNWXSVZTG-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxypropanoic acid Chemical compound OC(=O)C(C)OP(O)(=O)CC1=CC=CC=C1 PYGHZFNWXSVZTG-UHFFFAOYSA-N 0.000 description 4
WOXYAGIFVNOHDP-UHFFFAOYSA-N 2-[butyl(hydroxy)phosphoryl]oxy-2-phenylacetic acid Chemical compound CCCCP(O)(=O)OC(C(O)=O)C1=CC=CC=C1 WOXYAGIFVNOHDP-UHFFFAOYSA-N 0.000 description 4
NQGDLZOYLCNOSC-UHFFFAOYSA-N 2-[cyclohexyl(hydroxy)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)C1CCCCC1 NQGDLZOYLCNOSC-UHFFFAOYSA-N 0.000 description 4
VCBDYWLTMXLYQN-UHFFFAOYSA-N 2-[cyclohexyl(hydroxy)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)C1CCCCC1 VCBDYWLTMXLYQN-UHFFFAOYSA-N 0.000 description 4
XKHNAMYYAIKNLY-UHFFFAOYSA-N 2-[hydroxy(2-phenylethyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CCC1=CC=CC=C1 XKHNAMYYAIKNLY-UHFFFAOYSA-N 0.000 description 4
KGDTVWQZSRRMKH-UHFFFAOYSA-N 2-[hydroxy(3-phenylpropyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CCCC1=CC=CC=C1 KGDTVWQZSRRMKH-UHFFFAOYSA-N 0.000 description 4
VJTRRSNZACAQQJ-UHFFFAOYSA-N 2-[hydroxy(3-pyridin-3-ylpropyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CCCC1=CC=CN=C1 VJTRRSNZACAQQJ-UHFFFAOYSA-N 0.000 description 4
YOAXHSPRZGSXCE-UHFFFAOYSA-N 2-[hydroxy(4-naphthalen-2-ylbutyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1CCCCP(O)(=O)OC(C(=O)O)C1=CC=CC=C1 YOAXHSPRZGSXCE-UHFFFAOYSA-N 0.000 description 4
BUPIQYUMRMOTDA-UHFFFAOYSA-N 2-[hydroxy(4-naphthalen-2-ylbutyl)phosphoryl]oxypentanedioic acid Chemical compound C1=CC=CC2=CC(CCCCP(O)(=O)OC(CCC(=O)O)C(O)=O)=CC=C21 BUPIQYUMRMOTDA-UHFFFAOYSA-N 0.000 description 4
CSFIKDGMDKEDSF-UHFFFAOYSA-N 2-[hydroxy(4-phenylbutyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CCCCC1=CC=CC=C1 CSFIKDGMDKEDSF-UHFFFAOYSA-N 0.000 description 4
WVAKLFUQXGJVBI-UHFFFAOYSA-N 2-[hydroxy-[3-(1h-indol-3-yl)propyl]phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1NC2=CC=CC=C2C=1CCCP(O)(=O)OC(C(=O)O)C1=CC=CC=C1 WVAKLFUQXGJVBI-UHFFFAOYSA-N 0.000 description 4
AUXGATHBVRIBOG-UHFFFAOYSA-N 2-[hydroxy-[3-(oxolan-2-yl)propyl]phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CCCC1CCCO1 AUXGATHBVRIBOG-UHFFFAOYSA-N 0.000 description 4
XSHDTACHGSRUCB-UHFFFAOYSA-N 2-benzyl-3-[benzyl(hydroxy)phosphoryl]propanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)CC(C(=O)O)CC1=CC=CC=C1 XSHDTACHGSRUCB-UHFFFAOYSA-N 0.000 description 4
DLTMOQHVJJRACK-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(1h-indol-2-yl)-2-methylpropanoic acid Chemical compound C=1C2=CC=CC=C2NC=1C(C)(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 DLTMOQHVJJRACK-UHFFFAOYSA-N 0.000 description 4
IXUGBBOXLJOJGI-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(1h-indol-4-yl)-2-methylpropanoic acid Chemical compound C=1C=CC=2NC=CC=2C=1C(C)(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 IXUGBBOXLJOJGI-UHFFFAOYSA-N 0.000 description 4
XZEOIXLHOSBXEF-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(2,3,4-trimethoxyphenyl)propanoic acid Chemical compound COC1=C(OC)C(OC)=CC=C1C(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 XZEOIXLHOSBXEF-UHFFFAOYSA-N 0.000 description 4
KXWUBFRDSSFERK-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-cyclohexyl-2-methylpropanoic acid Chemical compound C1CCCCC1C(C(O)=O)(C)CP(O)(=O)CC1=CC=CC=C1 KXWUBFRDSSFERK-UHFFFAOYSA-N 0.000 description 4
ZSHCQIOISDIWGL-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-cyclohexylpropanoic acid Chemical compound C1CCCCC1C(C(=O)O)CP(O)(=O)CC1=CC=CC=C1 ZSHCQIOISDIWGL-UHFFFAOYSA-N 0.000 description 4
NTEJCKVCBCWPEK-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-methyl-2-(oxolan-2-yl)propanoic acid Chemical compound C1CCOC1C(C(O)=O)(C)CP(O)(=O)CC1=CC=CC=C1 NTEJCKVCBCWPEK-UHFFFAOYSA-N 0.000 description 4
COYJUWGJTSURRI-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-methyl-2-naphthalen-1-ylpropanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1C(C)(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 COYJUWGJTSURRI-UHFFFAOYSA-N 0.000 description 4
WTSAEGZPDCGNGJ-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-methyl-2-naphthalen-2-ylpropanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C(C)(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 WTSAEGZPDCGNGJ-UHFFFAOYSA-N 0.000 description 4
PYQCSGKSAIGFRN-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-methyl-2-pyridin-3-ylpropanoic acid Chemical compound C=1C=CN=CC=1C(C)(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 PYQCSGKSAIGFRN-UHFFFAOYSA-N 0.000 description 4
WXSUMMCEBATBPT-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-methylpropanoic acid Chemical compound OC(=O)C(C)CP(O)(=O)CC1=CC=CC=C1 WXSUMMCEBATBPT-UHFFFAOYSA-N 0.000 description 4
WTCYTSYCCZAADD-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-naphthalen-1-ylpropanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1C(C(=O)O)CP(O)(=O)CC1=CC=CC=C1 WTCYTSYCCZAADD-UHFFFAOYSA-N 0.000 description 4
KSLDFPBNURSPGP-UHFFFAOYSA-N 3-[hydroxy(2-phenylethyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CCC1=CC=CC=C1 KSLDFPBNURSPGP-UHFFFAOYSA-N 0.000 description 4
FZJLDMBSZBGDQB-UHFFFAOYSA-N 3-[hydroxy(3-naphthalen-1-ylpropyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1CCCP(O)(=O)CC(C(=O)O)C1=CC=CC=C1 FZJLDMBSZBGDQB-UHFFFAOYSA-N 0.000 description 4
PYSRURMLDGUHRL-UHFFFAOYSA-N 3-[hydroxy(3-phenylprop-2-enyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CC=CC1=CC=CC=C1 PYSRURMLDGUHRL-UHFFFAOYSA-N 0.000 description 4
UYLYDOZISIFBMQ-UHFFFAOYSA-N 3-[hydroxy(3-phenylpropyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CCCC1=CC=CC=C1 UYLYDOZISIFBMQ-UHFFFAOYSA-N 0.000 description 4
XDSNFRMOSGRMCG-UHFFFAOYSA-N 3-[hydroxy(4-naphthalen-1-ylbutyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1CCCCP(O)(=O)CC(C(=O)O)C1=CC=CC=C1 XDSNFRMOSGRMCG-UHFFFAOYSA-N 0.000 description 4
JXJUSWVXKYSLSJ-UHFFFAOYSA-N 3-[hydroxy(4-naphthalen-2-ylbutyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1CCCCP(O)(=O)CC(C(=O)O)C1=CC=CC=C1 JXJUSWVXKYSLSJ-UHFFFAOYSA-N 0.000 description 4
FNBYCCJZZSVSTQ-UHFFFAOYSA-N 3-[hydroxy(phenyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)C1=CC=CC=C1 FNBYCCJZZSVSTQ-UHFFFAOYSA-N 0.000 description 4
MZKFOLGZZUBJLH-UHFFFAOYSA-N 3-[hydroxy(propyl)phosphoryl]-2-phenylpropanoic acid Chemical compound CCCP(O)(=O)CC(C(O)=O)C1=CC=CC=C1 MZKFOLGZZUBJLH-UHFFFAOYSA-N 0.000 description 4
ZNXPPNZQUBPZBI-UHFFFAOYSA-N 4-[[benzyl(hydroxy)phosphoryl]amino]-4-(1h-indol-3-yl)pentanoic acid Chemical compound C=1NC2=CC=CC=C2C=1C(CCC(O)=O)(C)NP(O)(=O)CC1=CC=CC=C1 ZNXPPNZQUBPZBI-UHFFFAOYSA-N 0.000 description 4
IKYGLTBTEGJMMU-UHFFFAOYSA-N 4-[[benzyl(hydroxy)phosphoryl]amino]-4-naphthalen-1-ylhexanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1C(CCC(O)=O)(CC)NP(O)(=O)CC1=CC=CC=C1 IKYGLTBTEGJMMU-UHFFFAOYSA-N 0.000 description 4
WOYBEXCDWPFUHB-UHFFFAOYSA-N 4-[[benzyl(hydroxy)phosphoryl]amino]-4-naphthalen-1-ylpentanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1C(CCC(O)=O)(C)NP(O)(=O)CC1=CC=CC=C1 WOYBEXCDWPFUHB-UHFFFAOYSA-N 0.000 description 4
GITGSSQEALCKRN-UHFFFAOYSA-N 4-[[benzyl(hydroxy)phosphoryl]amino]-4-naphthalen-2-ylbutanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C(CCC(=O)O)NP(O)(=O)CC1=CC=CC=C1 GITGSSQEALCKRN-UHFFFAOYSA-N 0.000 description 4
UIJQAJQTJLIPJL-UHFFFAOYSA-N 4-[[benzyl(hydroxy)phosphoryl]amino]-4-naphthalen-2-ylhexanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C(CCC(O)=O)(CC)NP(O)(=O)CC1=CC=CC=C1 UIJQAJQTJLIPJL-UHFFFAOYSA-N 0.000 description 4
MCCMYUKNTMQNSK-UHFFFAOYSA-N 4-[[benzyl(hydroxy)phosphoryl]amino]-4-naphthalen-2-ylpentanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C(CCC(O)=O)(C)NP(O)(=O)CC1=CC=CC=C1 MCCMYUKNTMQNSK-UHFFFAOYSA-N 0.000 description 4
OPXGIVNMRSATSF-UHFFFAOYSA-N 4-[[benzyl(hydroxy)phosphoryl]amino]-4-phenylbutanoic acid Chemical compound C=1C=CC=CC=1C(CCC(=O)O)NP(O)(=O)CC1=CC=CC=C1 OPXGIVNMRSATSF-UHFFFAOYSA-N 0.000 description 4
UQSRGNPWQVOPGO-UHFFFAOYSA-N 4-[[benzyl(hydroxy)phosphoryl]amino]-4-phenylhexanoic acid Chemical compound C=1C=CC=CC=1C(CCC(O)=O)(CC)NP(O)(=O)CC1=CC=CC=C1 UQSRGNPWQVOPGO-UHFFFAOYSA-N 0.000 description 4
NDJIQPJNCJLIHN-UHFFFAOYSA-N 4-[[benzyl(hydroxy)phosphoryl]amino]-4-phenylpentanoic acid Chemical compound C=1C=CC=CC=1C(CCC(O)=O)(C)NP(O)(=O)CC1=CC=CC=C1 NDJIQPJNCJLIHN-UHFFFAOYSA-N 0.000 description 4
AQKVDVBYFDTBBN-UHFFFAOYSA-N 4-[[benzyl(hydroxy)phosphoryl]amino]-4-pyridin-3-ylpentanoic acid Chemical compound C=1C=CN=CC=1C(CCC(O)=O)(C)NP(O)(=O)CC1=CC=CC=C1 AQKVDVBYFDTBBN-UHFFFAOYSA-N 0.000 description 4
MOJJXGCVKIGKQY-UHFFFAOYSA-N 4-[benzyl(hydroxy)phosphoryl]oxy-4-(1h-indol-3-yl)butanoic acid Chemical compound C=1NC2=CC=CC=C2C=1C(CCC(=O)O)OP(O)(=O)CC1=CC=CC=C1 MOJJXGCVKIGKQY-UHFFFAOYSA-N 0.000 description 4
YIOWANGLQLAABQ-UHFFFAOYSA-N 4-[benzyl(hydroxy)phosphoryl]oxy-4-naphthalen-1-ylhexanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1C(CCC(O)=O)(CC)OP(O)(=O)CC1=CC=CC=C1 YIOWANGLQLAABQ-UHFFFAOYSA-N 0.000 description 4
ZLTAGLMTHQGSKR-UHFFFAOYSA-N 4-[benzyl(hydroxy)phosphoryl]oxy-4-naphthalen-2-ylbutanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C(CCC(=O)O)OP(O)(=O)CC1=CC=CC=C1 ZLTAGLMTHQGSKR-UHFFFAOYSA-N 0.000 description 4
WSCNRWNOQPXPMD-UHFFFAOYSA-N 4-[benzyl(hydroxy)phosphoryl]oxy-4-naphthalen-2-ylhexanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C(CCC(O)=O)(CC)OP(O)(=O)CC1=CC=CC=C1 WSCNRWNOQPXPMD-UHFFFAOYSA-N 0.000 description 4
GZNCYPMIPMTKAY-UHFFFAOYSA-N 4-[benzyl(hydroxy)phosphoryl]oxy-4-naphthalen-2-ylpentanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C(CCC(O)=O)(C)OP(O)(=O)CC1=CC=CC=C1 GZNCYPMIPMTKAY-UHFFFAOYSA-N 0.000 description 4
OPJXXPVLNJBBJU-UHFFFAOYSA-N 4-[benzyl(hydroxy)phosphoryl]oxy-4-phenylbutanoic acid Chemical compound C=1C=CC=CC=1C(CCC(=O)O)OP(O)(=O)CC1=CC=CC=C1 OPJXXPVLNJBBJU-UHFFFAOYSA-N 0.000 description 4
DJKVLSLZRAJINU-UHFFFAOYSA-N 4-[benzyl(hydroxy)phosphoryl]oxy-4-phenylhexanoic acid Chemical compound C=1C=CC=CC=1C(CCC(O)=O)(CC)OP(O)(=O)CC1=CC=CC=C1 DJKVLSLZRAJINU-UHFFFAOYSA-N 0.000 description 4
VOEDZVPNOHDTBG-UHFFFAOYSA-N 4-[benzyl(hydroxy)phosphoryl]oxy-4-phenylpentanoic acid Chemical compound C=1C=CC=CC=1C(CCC(O)=O)(C)OP(O)(=O)CC1=CC=CC=C1 VOEDZVPNOHDTBG-UHFFFAOYSA-N 0.000 description 4
HFWRZJQETGIRDY-UHFFFAOYSA-N 4-[benzyl(hydroxy)phosphoryl]oxy-4-pyridin-3-ylpentanoic acid Chemical compound C=1C=CN=CC=1C(CCC(O)=O)(C)OP(O)(=O)CC1=CC=CC=C1 HFWRZJQETGIRDY-UHFFFAOYSA-N 0.000 description 4
BBGFNFXNWHXOAY-UHFFFAOYSA-N 4-[benzyl(hydroxy)phosphoryl]oxy-4-thiophen-3-ylbutanoic acid Chemical compound C1=CSC=C1C(CCC(=O)O)OP(O)(=O)CC1=CC=CC=C1 BBGFNFXNWHXOAY-UHFFFAOYSA-N 0.000 description 4
QBLVIYYIUGORKJ-UHFFFAOYSA-N 5-[benzyl(hydroxy)phosphoryl]-2-methyl-4-(oxolan-2-yl)pentanoic acid Chemical compound C1CCOC1C(CC(C)C(O)=O)CP(O)(=O)CC1=CC=CC=C1 QBLVIYYIUGORKJ-UHFFFAOYSA-N 0.000 description 4
RSMYZJJZDVDHHX-UHFFFAOYSA-N 5-[benzyl(hydroxy)phosphoryl]-2-methyl-4-naphthalen-1-ylhexanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1C(CC(C)C(O)=O)C(C)P(O)(=O)CC1=CC=CC=C1 RSMYZJJZDVDHHX-UHFFFAOYSA-N 0.000 description 4
GYOJIGLUCRQFMV-UHFFFAOYSA-N 5-[benzyl(hydroxy)phosphoryl]-2-methyl-4-naphthalen-1-ylpentanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1C(CC(C)C(O)=O)CP(O)(=O)CC1=CC=CC=C1 GYOJIGLUCRQFMV-UHFFFAOYSA-N 0.000 description 4
HOVOHZNCQMIIRM-UHFFFAOYSA-N 5-[benzyl(hydroxy)phosphoryl]-2-methyl-4-phenylpent-4-enoic acid Chemical compound C=1C=CC=CC=1C(CC(C)C(O)=O)=CP(O)(=O)CC1=CC=CC=C1 HOVOHZNCQMIIRM-UHFFFAOYSA-N 0.000 description 4
OLUZXFJLEISQEA-UHFFFAOYSA-N 5-[benzyl(hydroxy)phosphoryl]-2-methyl-4-pyridin-3-ylpentanoic acid Chemical compound C=1C=CN=CC=1C(CC(C)C(O)=O)CP(O)(=O)CC1=CC=CC=C1 OLUZXFJLEISQEA-UHFFFAOYSA-N 0.000 description 4
QGIDPGMCXYGTLX-UHFFFAOYSA-N 5-[benzyl(hydroxy)phosphoryl]-2-methyl-4-thiophen-3-ylpentanoic acid Chemical compound C1=CSC=C1C(CC(C)C(O)=O)CP(O)(=O)CC1=CC=CC=C1 QGIDPGMCXYGTLX-UHFFFAOYSA-N 0.000 description 4
MTWVYGIIHVUGNL-UHFFFAOYSA-N CCCCP(O)=O Chemical compound CCCCP(O)=O MTWVYGIIHVUGNL-UHFFFAOYSA-N 0.000 description 4
201000009030 Carcinoma Diseases 0.000 description 4
208000022072 Gallbladder Neoplasms Diseases 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
208000007766 Kaposi sarcoma Diseases 0.000 description 4
206010061902 Pancreatic neoplasm Diseases 0.000 description 4
208000021712 Soft tissue sarcoma Diseases 0.000 description 4
208000006105 Uterine Cervical Neoplasms Diseases 0.000 description 4
230000005856 abnormality Effects 0.000 description 4
206010002026 amyotrophic lateral sclerosis Diseases 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
239000008280 blood Substances 0.000 description 4
201000010881 cervical cancer Diseases 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
238000002512 chemotherapy Methods 0.000 description 4
239000012091 fetal bovine serum Substances 0.000 description 4
230000006870 function Effects 0.000 description 4
201000010175 gallbladder cancer Diseases 0.000 description 4
210000004602 germ cell Anatomy 0.000 description 4
230000003054 hormonal effect Effects 0.000 description 4
238000002513 implantation Methods 0.000 description 4
238000010348 incorporation Methods 0.000 description 4
238000001802 infusion Methods 0.000 description 4
238000011221 initial treatment Methods 0.000 description 4
208000015486 malignant pancreatic neoplasm Diseases 0.000 description 4
125000006178 methyl benzyl group Chemical group 0.000 description 4
239000002858 neurotransmitter agent Substances 0.000 description 4
201000002528 pancreatic cancer Diseases 0.000 description 4
208000008443 pancreatic carcinoma Diseases 0.000 description 4
239000008194 pharmaceutical composition Substances 0.000 description 4
230000003389 potentiating effect Effects 0.000 description 4
239000000047 product Substances 0.000 description 4
238000011084 recovery Methods 0.000 description 4
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
238000007619 statistical method Methods 0.000 description 4
230000004083 survival effect Effects 0.000 description 4
238000002560 therapeutic procedure Methods 0.000 description 4
238000004809 thin layer chromatography Methods 0.000 description 4
230000000699 topical effect Effects 0.000 description 4
230000004614 tumor growth Effects 0.000 description 4
239000003981 vehicle Substances 0.000 description 4
OGNSCSPNOLGXSM-UHFFFAOYSA-N (+/-)-DABA Natural products NCCC(N)C(O)=O OGNSCSPNOLGXSM-UHFFFAOYSA-N 0.000 description 3
LHGLZDZEXMOSEG-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-(1h-indol-3-yl)propanoic acid Chemical compound C=1NC2=CC=CC=C2C=1C(C)(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 LHGLZDZEXMOSEG-UHFFFAOYSA-N 0.000 description 3
CYENMZNXEPPUEN-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-naphthalen-1-ylpropanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1C(C)(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 CYENMZNXEPPUEN-UHFFFAOYSA-N 0.000 description 3
PVONDGBJSLMQIL-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-pyridin-2-ylpropanoic acid Chemical compound C=1C=CC=NC=1C(C)(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 PVONDGBJSLMQIL-UHFFFAOYSA-N 0.000 description 3
FKWRTDPHLPTAFE-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]decanedioic acid Chemical compound OC(=O)CCCCCCCC(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 FKWRTDPHLPTAFE-UHFFFAOYSA-N 0.000 description 3
PGUIGLVWQCAOJE-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]hexanoic acid Chemical compound CCCCC(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 PGUIGLVWQCAOJE-UHFFFAOYSA-N 0.000 description 3
QBMMJWNQOYYRNY-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]methyl]-4-(1h-indol-3-yl)butanoic acid Chemical compound C=1NC2=CC=CC=C2C=1CCC(C(=O)O)CP(O)(=O)CC1=CC=CC=C1 QBMMJWNQOYYRNY-UHFFFAOYSA-N 0.000 description 3
XSISPHRKZWALMD-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]methyl]-4-pyridin-3-ylbutanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)CC(C(=O)O)CCC1=CC=CN=C1 XSISPHRKZWALMD-UHFFFAOYSA-N 0.000 description 3
MZIJVVNFYDOQCI-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]methyl]-4-thiophen-3-ylbutanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)CC(C(=O)O)CCC=1C=CSC=1 MZIJVVNFYDOQCI-UHFFFAOYSA-N 0.000 description 3
JKZXBDRABMCQRB-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]methyl]decanedioic acid Chemical compound OC(=O)CCCCCCCC(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 JKZXBDRABMCQRB-UHFFFAOYSA-N 0.000 description 3
CTSPHXFDBJBTFS-UHFFFAOYSA-N 2-[[cyclohexyl(hydroxy)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)C1CCCCC1 CTSPHXFDBJBTFS-UHFFFAOYSA-N 0.000 description 3
UNHSYVCKZOSDNN-UHFFFAOYSA-N 2-[[cyclohexyl(hydroxy)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C1CCCCC1 UNHSYVCKZOSDNN-UHFFFAOYSA-N 0.000 description 3
QMCBYHRSIMWBDI-UHFFFAOYSA-N 2-[[hydroxy(3-naphthalen-1-ylpropyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC2=CC=CC=C2C=1CCCP(O)(=O)NC(C(=O)O)C1=CC=CC=C1 QMCBYHRSIMWBDI-UHFFFAOYSA-N 0.000 description 3
MKIHUHTXLFYLLI-UHFFFAOYSA-N 2-[[hydroxy(3-naphthalen-1-ylpropyl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=C2C(CCCP(O)(=O)CC(CCC(=O)O)C(O)=O)=CC=CC2=C1 MKIHUHTXLFYLLI-UHFFFAOYSA-N 0.000 description 3
AMLXFGLQNBYPCM-UHFFFAOYSA-N 2-[[hydroxy(3-naphthalen-2-ylpropyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1CCCP(O)(=O)NC(C(=O)O)C1=CC=CC=C1 AMLXFGLQNBYPCM-UHFFFAOYSA-N 0.000 description 3
PRTNGULNICUYDB-UHFFFAOYSA-N 2-[[hydroxy(3-phenylpropyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CCCC1=CC=CC=C1 PRTNGULNICUYDB-UHFFFAOYSA-N 0.000 description 3
XTIITZYXBXVEQJ-UHFFFAOYSA-N 2-[[hydroxy(3-thiophen-3-ylpropyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CCCC=1C=CSC=1 XTIITZYXBXVEQJ-UHFFFAOYSA-N 0.000 description 3
BZRISOPJAUFGJC-UHFFFAOYSA-N 2-[[hydroxy(4-phenylbutyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CCCCC1=CC=CC=C1 BZRISOPJAUFGJC-UHFFFAOYSA-N 0.000 description 3
ZLVSTOJKRGCGEB-UHFFFAOYSA-N 2-[[hydroxy(4-phenylbutyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CCCCC1=CC=CC=C1 ZLVSTOJKRGCGEB-UHFFFAOYSA-N 0.000 description 3
MSHOTVDNUHSOIV-UHFFFAOYSA-N 2-[[hydroxy(propyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound CCCP(O)(=O)NC(C(O)=O)C1=CC=CC=C1 MSHOTVDNUHSOIV-UHFFFAOYSA-N 0.000 description 3
XQFINHZUZNLWMM-UHFFFAOYSA-N 2-[[hydroxy(propyl)phosphoryl]amino]pentanedioic acid Chemical compound CCCP(O)(=O)NC(C(O)=O)CCC(O)=O XQFINHZUZNLWMM-UHFFFAOYSA-N 0.000 description 3
AZKGHVHHPVBNSQ-UHFFFAOYSA-N 2-[[hydroxy-[3-(1h-indol-3-yl)propyl]phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1NC2=CC=CC=C2C=1CCCP(O)(=O)NC(C(=O)O)C1=CC=CC=C1 AZKGHVHHPVBNSQ-UHFFFAOYSA-N 0.000 description 3
OQLOHCMHHRCBLV-UHFFFAOYSA-N 2-[[hydroxy-[3-(1h-indol-3-yl)propyl]phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=C2C(CCCP(O)(=O)CC(CCC(=O)O)C(O)=O)=CNC2=C1 OQLOHCMHHRCBLV-UHFFFAOYSA-N 0.000 description 3
QVZDQCQYYJQTLF-UHFFFAOYSA-N 2-[[hydroxy-[hydroxy(phenyl)methyl]phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)C(O)C1=CC=CC=C1 QVZDQCQYYJQTLF-UHFFFAOYSA-N 0.000 description 3
DLGFIRCMQJRXOV-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-(1h-indol-2-yl)propanoic acid Chemical compound C=1C2=CC=CC=C2NC=1C(C)(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 DLGFIRCMQJRXOV-UHFFFAOYSA-N 0.000 description 3
VDXWCPBWSJEOOE-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-(1h-indol-3-yl)propanoic acid Chemical compound C=1NC2=CC=CC=C2C=1C(C)(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 VDXWCPBWSJEOOE-UHFFFAOYSA-N 0.000 description 3
BFOOCNWSBXZRLE-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-(oxolan-2-yl)acetic acid Chemical compound C1CCOC1C(C(=O)O)OP(O)(=O)CC1=CC=CC=C1 BFOOCNWSBXZRLE-UHFFFAOYSA-N 0.000 description 3
RKURFKBXBKQSFR-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-naphthalen-2-ylacetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C(C(=O)O)OP(O)(=O)CC1=CC=CC=C1 RKURFKBXBKQSFR-UHFFFAOYSA-N 0.000 description 3
KXHRDIQDJAIJDY-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-naphthalen-2-ylpropanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C(C)(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 KXHRDIQDJAIJDY-UHFFFAOYSA-N 0.000 description 3
YDRJRWDSYGFWLT-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-pyridin-3-ylacetic acid Chemical compound C=1C=CN=CC=1C(C(=O)O)OP(O)(=O)CC1=CC=CC=C1 YDRJRWDSYGFWLT-UHFFFAOYSA-N 0.000 description 3
MHJXRSVKULVPHU-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-thiophen-2-ylacetic acid Chemical compound C=1C=CSC=1C(C(=O)O)OP(O)(=O)CC1=CC=CC=C1 MHJXRSVKULVPHU-UHFFFAOYSA-N 0.000 description 3
NQIUSGNGUVJBMC-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-3-phenylpropanoic acid Chemical compound C=1C=CC=CC=1CP(O)(=O)OC(C(=O)O)CC1=CC=CC=C1 NQIUSGNGUVJBMC-UHFFFAOYSA-N 0.000 description 3
VEYYGHSBJAUGOY-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxybutanoic acid Chemical compound CCC(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 VEYYGHSBJAUGOY-UHFFFAOYSA-N 0.000 description 3
BUIKGLWRLFSZGV-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxyhexanedioic acid Chemical compound OC(=O)CCCC(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 BUIKGLWRLFSZGV-UHFFFAOYSA-N 0.000 description 3
ZILHJNORCQQBFU-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxyhexanoic acid Chemical compound CCCCC(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 ZILHJNORCQQBFU-UHFFFAOYSA-N 0.000 description 3
LFMXWDFNWSFWNA-UHFFFAOYSA-N 2-[hydroxy(3-naphthalen-2-ylpropyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1CCCP(O)(=O)OC(C(=O)O)C1=CC=CC=C1 LFMXWDFNWSFWNA-UHFFFAOYSA-N 0.000 description 3
MFJRGMWGBWUCRB-UHFFFAOYSA-N 2-[hydroxy(3-phenylprop-2-enyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CC=CC1=CC=CC=C1 MFJRGMWGBWUCRB-UHFFFAOYSA-N 0.000 description 3
SYCJBCFTUFQBSI-UHFFFAOYSA-N 2-[hydroxy(3-thiophen-3-ylpropyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CCCC=1C=CSC=1 SYCJBCFTUFQBSI-UHFFFAOYSA-N 0.000 description 3
ACTRMXGOTXDGEZ-UHFFFAOYSA-N 2-[hydroxy(4-naphthalen-1-ylbutyl)phosphoryl]oxypentanedioic acid Chemical compound C1=CC=C2C(CCCCP(O)(=O)OC(CCC(=O)O)C(O)=O)=CC=CC2=C1 ACTRMXGOTXDGEZ-UHFFFAOYSA-N 0.000 description 3
BFKAVXJCFHYJQQ-UHFFFAOYSA-N 2-[hydroxy(methyl)phosphoryl]oxyoctanedioic acid Chemical compound CP(O)(=O)OC(C(O)=O)CCCCCC(O)=O BFKAVXJCFHYJQQ-UHFFFAOYSA-N 0.000 description 3
KHNADBNWXBMICF-UHFFFAOYSA-N 2-[hydroxy(propyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound CCCP(O)(=O)OC(C(O)=O)C1=CC=CC=C1 KHNADBNWXBMICF-UHFFFAOYSA-N 0.000 description 3
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 description 3
LNWLYVUSZAHNLC-UHFFFAOYSA-N 2-[hydroxy-[(4-methoxyphenyl)methyl]phosphoryl]oxypentanedioic acid Chemical compound COC1=CC=C(CP(O)(=O)OC(CCC(O)=O)C(O)=O)C=C1 LNWLYVUSZAHNLC-UHFFFAOYSA-N 0.000 description 3
YHSWFRGRZNDWFF-UHFFFAOYSA-N 2-[hydroxy-[3-(oxolan-2-yl)propyl]phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CCCC1CCCO1 YHSWFRGRZNDWFF-UHFFFAOYSA-N 0.000 description 3
RRTVXHNACTXIED-UHFFFAOYSA-N 2-[hydroxy-[hydroxy(phenyl)methyl]phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)C(O)C1=CC=CC=C1 RRTVXHNACTXIED-UHFFFAOYSA-N 0.000 description 3
DRVCWMWQLZCUCW-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(1h-indol-2-yl)propanoic acid Chemical compound C=1C2=CC=CC=C2NC=1C(C(=O)O)CP(O)(=O)CC1=CC=CC=C1 DRVCWMWQLZCUCW-UHFFFAOYSA-N 0.000 description 3
JQMAMWGGWKUKPE-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(1h-indol-3-yl)-2-methylpropanoic acid Chemical compound C=1NC2=CC=CC=C2C=1C(C)(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 JQMAMWGGWKUKPE-UHFFFAOYSA-N 0.000 description 3
FAPWLJXZHFJFKA-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(1h-indol-3-yl)propanoic acid Chemical compound C=1NC2=CC=CC=C2C=1C(C(=O)O)CP(O)(=O)CC1=CC=CC=C1 FAPWLJXZHFJFKA-UHFFFAOYSA-N 0.000 description 3
UMBWAGCSYHLQNG-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(1h-indol-4-yl)propanoic acid Chemical compound C=1C=CC=2NC=CC=2C=1C(C(=O)O)CP(O)(=O)CC1=CC=CC=C1 UMBWAGCSYHLQNG-UHFFFAOYSA-N 0.000 description 3
OXYQVTCJYQRFEQ-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-(oxolan-2-yl)propanoic acid Chemical compound C1CCOC1C(C(=O)O)CP(O)(=O)CC1=CC=CC=C1 OXYQVTCJYQRFEQ-UHFFFAOYSA-N 0.000 description 3
UDBZIILBASLOAS-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-methyl-2-pyridin-4-ylpropanoic acid Chemical compound C=1C=NC=CC=1C(C)(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 UDBZIILBASLOAS-UHFFFAOYSA-N 0.000 description 3
ODDOOMXBTVPKBD-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-methyl-2-thiophen-2-ylpropanoic acid Chemical compound C=1C=CSC=1C(C)(C(O)=O)CP(O)(=O)CC1=CC=CC=C1 ODDOOMXBTVPKBD-UHFFFAOYSA-N 0.000 description 3
VQFUFCPKSGHYPX-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-pyridin-2-ylpropanoic acid Chemical compound C=1C=CC=NC=1C(C(=O)O)CP(O)(=O)CC1=CC=CC=C1 VQFUFCPKSGHYPX-UHFFFAOYSA-N 0.000 description 3
QXSWRMFTFZAYIL-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-pyridin-3-ylpropanoic acid Chemical compound C=1C=CN=CC=1C(C(=O)O)CP(O)(=O)CC1=CC=CC=C1 QXSWRMFTFZAYIL-UHFFFAOYSA-N 0.000 description 3
ZYYVKLFLPNRDSO-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-pyridin-4-ylpropanoic acid Chemical compound C=1C=NC=CC=1C(C(=O)O)CP(O)(=O)CC1=CC=CC=C1 ZYYVKLFLPNRDSO-UHFFFAOYSA-N 0.000 description 3
DKGRWTRMSBRBLC-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-thiophen-2-ylpropanoic acid Chemical compound C=1C=CSC=1C(C(=O)O)CP(O)(=O)CC1=CC=CC=C1 DKGRWTRMSBRBLC-UHFFFAOYSA-N 0.000 description 3
VXTYCNHIUUKRFH-UHFFFAOYSA-N 3-[butyl(hydroxy)phosphoryl]-2-phenylpropanoic acid Chemical compound CCCCP(O)(=O)CC(C(O)=O)C1=CC=CC=C1 VXTYCNHIUUKRFH-UHFFFAOYSA-N 0.000 description 3
XPEWMQREDBFBJC-UHFFFAOYSA-N 3-[cyclohexyl(hydroxy)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)C1CCCCC1 XPEWMQREDBFBJC-UHFFFAOYSA-N 0.000 description 3
DWFOQSGAALKVMG-UHFFFAOYSA-N 3-[hydroxy(3-naphthalen-2-ylpropyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1CCCP(O)(=O)CC(C(=O)O)C1=CC=CC=C1 DWFOQSGAALKVMG-UHFFFAOYSA-N 0.000 description 3
ACXMYSKIZSWZHU-UHFFFAOYSA-N 3-[hydroxy(3-thiophen-3-ylpropyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CCCC=1C=CSC=1 ACXMYSKIZSWZHU-UHFFFAOYSA-N 0.000 description 3
SKZSVSNDQUJQEN-UHFFFAOYSA-N 3-[hydroxy(4-phenylbutyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CCCCC1=CC=CC=C1 SKZSVSNDQUJQEN-UHFFFAOYSA-N 0.000 description 3
AMCRIRHCVURBIY-UHFFFAOYSA-N 3-[hydroxy-[3-(1h-indol-3-yl)propyl]phosphoryl]-2-phenylpropanoic acid Chemical compound C=1NC2=CC=CC=C2C=1CCCP(O)(=O)CC(C(=O)O)C1=CC=CC=C1 AMCRIRHCVURBIY-UHFFFAOYSA-N 0.000 description 3
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 description 3
NBHIERRLCLQSMV-UHFFFAOYSA-N 4-[[benzyl(hydroxy)phosphoryl]amino]-4-(1h-indol-3-yl)butanoic acid Chemical compound C=1NC2=CC=CC=C2C=1C(CCC(=O)O)NP(O)(=O)CC1=CC=CC=C1 NBHIERRLCLQSMV-UHFFFAOYSA-N 0.000 description 3
CFGNMETVFPEVFW-UHFFFAOYSA-N 4-[[benzyl(hydroxy)phosphoryl]amino]-4-naphthalen-1-ylbutanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1C(CCC(=O)O)NP(O)(=O)CC1=CC=CC=C1 CFGNMETVFPEVFW-UHFFFAOYSA-N 0.000 description 3
WMXVVNNQAAETGP-UHFFFAOYSA-N 4-[[benzyl(hydroxy)phosphoryl]amino]-4-thiophen-3-ylbutanoic acid Chemical compound C1=CSC=C1C(CCC(=O)O)NP(O)(=O)CC1=CC=CC=C1 WMXVVNNQAAETGP-UHFFFAOYSA-N 0.000 description 3
ZXYGBQBCAWINOY-UHFFFAOYSA-N 4-[[benzyl(hydroxy)phosphoryl]amino]-4-thiophen-3-ylpentanoic acid Chemical compound C1=CSC=C1C(CCC(O)=O)(C)NP(O)(=O)CC1=CC=CC=C1 ZXYGBQBCAWINOY-UHFFFAOYSA-N 0.000 description 3
XXMYFSAKLRPRNJ-UHFFFAOYSA-N 4-[benzyl(hydroxy)phosphoryl]oxy-4-naphthalen-1-ylbutanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1C(CCC(=O)O)OP(O)(=O)CC1=CC=CC=C1 XXMYFSAKLRPRNJ-UHFFFAOYSA-N 0.000 description 3
WWQDJLDAFDMNLD-UHFFFAOYSA-N 4-[benzyl(hydroxy)phosphoryl]oxy-4-naphthalen-1-ylpentanoic acid Chemical compound C=1C=CC2=CC=CC=C2C=1C(CCC(O)=O)(C)OP(O)(=O)CC1=CC=CC=C1 WWQDJLDAFDMNLD-UHFFFAOYSA-N 0.000 description 3
SBVYQIHMMKDVDH-UHFFFAOYSA-N 4-[benzyl(hydroxy)phosphoryl]oxy-4-pyridin-3-ylbutanoic acid Chemical compound C=1C=CN=CC=1C(CCC(=O)O)OP(O)(=O)CC1=CC=CC=C1 SBVYQIHMMKDVDH-UHFFFAOYSA-N 0.000 description 3
ONCYCAFOKPKBGR-UHFFFAOYSA-N 4-[benzyl(hydroxy)phosphoryl]oxy-4-thiophen-3-ylpentanoic acid Chemical compound C1=CSC=C1C(CCC(O)=O)(C)OP(O)(=O)CC1=CC=CC=C1 ONCYCAFOKPKBGR-UHFFFAOYSA-N 0.000 description 3
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 description 3
BZCPVJFQEADCHA-UHFFFAOYSA-N 5-[benzyl(hydroxy)phosphoryl]-2-methyl-4-naphthalen-2-ylhexanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C(CC(C)C(O)=O)C(C)P(O)(=O)CC1=CC=CC=C1 BZCPVJFQEADCHA-UHFFFAOYSA-N 0.000 description 3
TWIGDGAQNMQPEV-UHFFFAOYSA-N 5-[benzyl(hydroxy)phosphoryl]-2-methyl-4-naphthalen-2-ylpentanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C(CC(C)C(O)=O)CP(O)(=O)CC1=CC=CC=C1 TWIGDGAQNMQPEV-UHFFFAOYSA-N 0.000 description 3
NQRRSWVLQGDWNK-UHFFFAOYSA-N 5-[benzyl(hydroxy)phosphoryl]-2-methyl-4-phenylhexanoic acid Chemical compound C=1C=CC=CC=1C(CC(C)C(O)=O)C(C)P(O)(=O)CC1=CC=CC=C1 NQRRSWVLQGDWNK-UHFFFAOYSA-N 0.000 description 3
IYQYYNPYHAAPDB-UHFFFAOYSA-N 5-[benzyl(hydroxy)phosphoryl]-2-methyl-4-phenylpentanoic acid Chemical compound C=1C=CC=CC=1C(CC(C)C(O)=O)CP(O)(=O)CC1=CC=CC=C1 IYQYYNPYHAAPDB-UHFFFAOYSA-N 0.000 description 3
POSGURUHYBGOAO-UHFFFAOYSA-N 5-[benzyl(hydroxy)phosphoryl]-4-(1h-indol-3-yl)-2-methylpentanoic acid Chemical compound C=1NC2=CC=CC=C2C=1C(CC(C)C(O)=O)CP(O)(=O)CC1=CC=CC=C1 POSGURUHYBGOAO-UHFFFAOYSA-N 0.000 description 3
101800000112 Acidic peptide Proteins 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
206010008342 Cervix carcinoma Diseases 0.000 description 3
206010010904 Convulsion Diseases 0.000 description 3
206010063045 Effusion Diseases 0.000 description 3
GHASVSINZRGABV-UHFFFAOYSA-N Fluorouracil Chemical compound FC1=CNC(=O)NC1=O GHASVSINZRGABV-UHFFFAOYSA-N 0.000 description 3
206010026673 Malignant Pleural Effusion Diseases 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
OTCCIMWXFLJLIA-UHFFFAOYSA-N N-acetyl-DL-aspartic acid Natural products CC(=O)NC(C(O)=O)CC(O)=O OTCCIMWXFLJLIA-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
239000012980 RPMI-1640 medium Substances 0.000 description 3
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
238000002679 ablation Methods 0.000 description 3
238000000540 analysis of variance Methods 0.000 description 3
IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
230000004663 cell proliferation Effects 0.000 description 3
TXHWYSOQHNMOOU-UHFFFAOYSA-N chloro(diethoxy)phosphane Chemical compound CCOP(Cl)OCC TXHWYSOQHNMOOU-UHFFFAOYSA-N 0.000 description 3
230000006957 competitive inhibition Effects 0.000 description 3
238000013270 controlled release Methods 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
229960004679 doxorubicin Drugs 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000012894 fetal calf serum Substances 0.000 description 3
238000001914 filtration Methods 0.000 description 3
229960002949 fluorouracil Drugs 0.000 description 3
238000009472 formulation Methods 0.000 description 3
229960003692 gamma aminobutyric acid Drugs 0.000 description 3
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000003550 marker Substances 0.000 description 3
239000000463 material Substances 0.000 description 3
230000003278 mimic effect Effects 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
235000019271 petrolatum Nutrition 0.000 description 3
125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 3
239000002243 precursor Substances 0.000 description 3
210000002307 prostate Anatomy 0.000 description 3
201000001514 prostate carcinoma Diseases 0.000 description 3
208000023958 prostate neoplasm Diseases 0.000 description 3
238000000746 purification Methods 0.000 description 3
238000001959 radiotherapy Methods 0.000 description 3
230000004044 response Effects 0.000 description 3
208000011581 secondary neoplasm Diseases 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 3
238000007920 subcutaneous administration Methods 0.000 description 3
230000000946 synaptic effect Effects 0.000 description 3
238000012360 testing method Methods 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
LZLYJQVFORDMDW-UHFFFAOYSA-N (5-oxo-5-phenylmethoxy-2-phenylmethoxycarbonylpentyl)phosphinic acid Chemical compound C=1C=CC=CC=1COC(=O)C(CP(=O)O)CCC(=O)OCC1=CC=CC=C1 LZLYJQVFORDMDW-UHFFFAOYSA-N 0.000 description 2
125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 description 2
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 2
VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 description 2
XOQVDBCNWPUEPS-UHFFFAOYSA-N 2-(phosphonomethyl)butanedioic acid Chemical compound OC(=O)CC(C(O)=O)CP(O)(O)=O XOQVDBCNWPUEPS-UHFFFAOYSA-N 0.000 description 2
FKXFVWAAUTYFQL-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-(2,3,4-trimethoxyphenyl)acetic acid Chemical compound COC1=C(OC)C(OC)=CC=C1C(C(O)=O)NP(O)(=O)CC1=CC=CC=C1 FKXFVWAAUTYFQL-UHFFFAOYSA-N 0.000 description 2
XWJHXJCFGVSEEM-UHFFFAOYSA-N 2-[[hydroxy(3-naphthalen-2-ylpropyl)phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=CC2=CC(CCCP(O)(=O)NC(CCC(=O)O)C(O)=O)=CC=C21 XWJHXJCFGVSEEM-UHFFFAOYSA-N 0.000 description 2
MGJIBTRRFMMOLR-UHFFFAOYSA-N 2-[[hydroxy(3-pyridin-3-ylpropyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)NP(O)(=O)CCCC1=CC=CN=C1 MGJIBTRRFMMOLR-UHFFFAOYSA-N 0.000 description 2
ACXVYIUXCQICJG-UHFFFAOYSA-N 2-[[hydroxy(3-pyridin-3-ylpropyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CCCC1=CC=CN=C1 ACXVYIUXCQICJG-UHFFFAOYSA-N 0.000 description 2
AIHGMOAYMBZROW-UHFFFAOYSA-N 2-[[hydroxy(3-thiophen-3-ylpropyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CCCC=1C=CSC=1 AIHGMOAYMBZROW-UHFFFAOYSA-N 0.000 description 2
YIZBKQQAPRYANP-UHFFFAOYSA-N 2-[[hydroxy(3-thiophen-3-ylpropyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CCCC=1C=CSC=1 YIZBKQQAPRYANP-UHFFFAOYSA-N 0.000 description 2
LKHZRTFVTVKKLZ-UHFFFAOYSA-N 2-[[hydroxy(4-naphthalen-1-ylbutyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=CC2=CC=CC=C2C=1CCCCP(O)(=O)NC(C(=O)O)C1=CC=CC=C1 LKHZRTFVTVKKLZ-UHFFFAOYSA-N 0.000 description 2
HLTOKVZRCAYHLA-UHFFFAOYSA-N 2-[[hydroxy(4-naphthalen-1-ylbutyl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=C2C(CCCCP(O)(=O)CC(CCC(=O)O)C(O)=O)=CC=CC2=C1 HLTOKVZRCAYHLA-UHFFFAOYSA-N 0.000 description 2
YHNLGZBVWKYYRG-UHFFFAOYSA-N 2-[[hydroxy(4-naphthalen-2-ylbutyl)phosphoryl]amino]-2-phenylacetic acid Chemical compound C=1C=C2C=CC=CC2=CC=1CCCCP(O)(=O)NC(C(=O)O)C1=CC=CC=C1 YHNLGZBVWKYYRG-UHFFFAOYSA-N 0.000 description 2
YRLBRICHQAYFGB-UHFFFAOYSA-N 2-[[hydroxy-[3-(1h-indol-3-yl)propyl]phosphoryl]amino]pentanedioic acid Chemical compound C1=CC=C2C(CCCP(O)(=O)NC(CCC(=O)O)C(O)=O)=CNC2=C1 YRLBRICHQAYFGB-UHFFFAOYSA-N 0.000 description 2
MOXMZILDSBXEBG-UHFFFAOYSA-N 2-[[hydroxy-[3-(oxolan-2-yl)propyl]phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CCCC1CCCO1 MOXMZILDSBXEBG-UHFFFAOYSA-N 0.000 description 2
YMKGTRQOJLBIPX-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-cyclohexylpropanoic acid Chemical compound C1CCCCC1C(C(O)=O)(C)OP(O)(=O)CC1=CC=CC=C1 YMKGTRQOJLBIPX-UHFFFAOYSA-N 0.000 description 2
MZARGCVRIJZCHL-UHFFFAOYSA-N 2-[hydroxy(3-naphthalen-1-ylpropyl)phosphoryl]oxypentanedioic acid Chemical compound C1=CC=C2C(CCCP(O)(=O)OC(CCC(=O)O)C(O)=O)=CC=CC2=C1 MZARGCVRIJZCHL-UHFFFAOYSA-N 0.000 description 2
XQAMBAHDAKOKCY-UHFFFAOYSA-N 2-[hydroxy(3-naphthalen-2-ylpropyl)phosphoryl]oxypentanedioic acid Chemical compound C1=CC=CC2=CC(CCCP(O)(=O)OC(CCC(=O)O)C(O)=O)=CC=C21 XQAMBAHDAKOKCY-UHFFFAOYSA-N 0.000 description 2
XQBQQOUCGFLXCS-UHFFFAOYSA-N 2-[hydroxy(3-pyridin-3-ylpropyl)phosphoryl]oxy-2-phenylacetic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)OP(O)(=O)CCCC1=CC=CN=C1 XQBQQOUCGFLXCS-UHFFFAOYSA-N 0.000 description 2
BKXUVLWVHQLSFC-UHFFFAOYSA-N 2-[hydroxy(3-thiophen-3-ylpropyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CCCC=1C=CSC=1 BKXUVLWVHQLSFC-UHFFFAOYSA-N 0.000 description 2
DRSIPFACHWRUMY-UHFFFAOYSA-N 2-[hydroxy(4-phenylbutyl)phosphoryl]oxypentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)OP(O)(=O)CCCCC1=CC=CC=C1 DRSIPFACHWRUMY-UHFFFAOYSA-N 0.000 description 2
OSSRYDZMQCWFDP-UHFFFAOYSA-N 2-[hydroxy-(2,3,4-trimethoxyphenyl)phosphoryl]oxypentanedioic acid Chemical compound COC1=CC=C(P(O)(=O)OC(CCC(O)=O)C(O)=O)C(OC)=C1OC OSSRYDZMQCWFDP-UHFFFAOYSA-N 0.000 description 2
MCGYWEKQJUXSII-UHFFFAOYSA-N 2-[hydroxy-[3-(1h-indol-3-yl)propyl]phosphoryl]oxypentanedioic acid Chemical compound C1=CC=C2C(CCCP(O)(=O)OC(CCC(=O)O)C(O)=O)=CNC2=C1 MCGYWEKQJUXSII-UHFFFAOYSA-N 0.000 description 2
125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 2
YIQLWJJOXXEUEY-UHFFFAOYSA-N 3-[[hydroxy(3-pyridin-3-ylpropyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CC(CC(O)=O)NP(O)(=O)CCCC1=CC=CN=C1 YIQLWJJOXXEUEY-UHFFFAOYSA-N 0.000 description 2
UOSFMVDHNULHHN-UHFFFAOYSA-N 3-[[hydroxy-[3-(oxolan-2-yl)propyl]phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CC(CC(O)=O)NP(O)(=O)CCCC1CCCO1 UOSFMVDHNULHHN-UHFFFAOYSA-N 0.000 description 2
QCRPBNCAWRRJBA-UHFFFAOYSA-N 3-[benzyl(hydroxy)phosphoryl]-2-naphthalen-2-ylpropanoic acid Chemical compound C=1C=C2C=CC=CC2=CC=1C(C(=O)O)CP(O)(=O)CC1=CC=CC=C1 QCRPBNCAWRRJBA-UHFFFAOYSA-N 0.000 description 2
QFRXPIRMVONBBC-UHFFFAOYSA-N 3-[hydroxy(3-pyridin-3-ylpropyl)phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CCCC1=CC=CN=C1 QFRXPIRMVONBBC-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
YURBAMPIDRARFA-UHFFFAOYSA-N 4-[[benzyl(hydroxy)phosphoryl]amino]-4-pyridin-3-ylbutanoic acid Chemical compound C=1C=CN=CC=1C(CCC(=O)O)NP(O)(=O)CC1=CC=CC=C1 YURBAMPIDRARFA-UHFFFAOYSA-N 0.000 description 2
HUKMAUATSQTPBQ-UHFFFAOYSA-N 4-[benzyl(hydroxy)phosphoryl]oxy-4-(1h-indol-3-yl)pentanoic acid Chemical compound C=1NC2=CC=CC=C2C=1C(CCC(O)=O)(C)OP(O)(=O)CC1=CC=CC=C1 HUKMAUATSQTPBQ-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
GVPIUBYPNJRTQD-UHFFFAOYSA-N C(C1=CC=CC=C1)OC(=O)C(C1=CC=CC=C1)P(O)(=O)CCCC Chemical compound C(C1=CC=CC=C1)OC(=O)C(C1=CC=CC=C1)P(O)(=O)CCCC GVPIUBYPNJRTQD-UHFFFAOYSA-N 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
CMSMOCZEIVJLDB-UHFFFAOYSA-N Cyclophosphamide Chemical compound ClCCN(CCCl)P1(=O)NCCCO1 CMSMOCZEIVJLDB-UHFFFAOYSA-N 0.000 description 2
238000009007 Diagnostic Kit Methods 0.000 description 2
208000006168 Ewing Sarcoma Diseases 0.000 description 2
108010069236 Goserelin Proteins 0.000 description 2
BLCLNMBMMGCOAS-URPVMXJPSA-N Goserelin Chemical compound C([C@@H](C(=O)N[C@H](COC(C)(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1[C@@H](CCC1)C(=O)NNC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)C1=CC=C(O)C=C1 BLCLNMBMMGCOAS-URPVMXJPSA-N 0.000 description 2
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
108010000817 Leuprolide Proteins 0.000 description 2
206010025323 Lymphomas Diseases 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
235000006679 Mentha X verticillata Nutrition 0.000 description 2
235000002899 Mentha suaveolens Nutrition 0.000 description 2
235000001636 Mentha x rotundifolia Nutrition 0.000 description 2
OTCCIMWXFLJLIA-BYPYZUCNSA-N N-acetyl-L-aspartic acid Chemical compound CC(=O)N[C@H](C(O)=O)CC(O)=O OTCCIMWXFLJLIA-BYPYZUCNSA-N 0.000 description 2
229920000305 Nylon 6,10 Polymers 0.000 description 2
239000004264 Petrolatum Substances 0.000 description 2
208000004965 Prostatic Intraepithelial Neoplasia Diseases 0.000 description 2
206010071019 Prostatic dysplasia Diseases 0.000 description 2
239000006146 Roswell Park Memorial Institute medium Substances 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
238000000692 Student's t-test Methods 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
JXLYSJRDGCGARV-WWYNWVTFSA-N Vinblastine Natural products O=C(O[C@H]1[C@](O)(C(=O)OC)[C@@H]2N(C)c3c(cc(c(OC)c3)[C@]3(C(=O)OC)c4[nH]c5c(c4CCN4C[C@](O)(CC)C[C@H](C3)C4)cccc5)[C@@]32[C@H]2[C@@]1(CC)C=CCN2CC3)C JXLYSJRDGCGARV-WWYNWVTFSA-N 0.000 description 2
229940022663 acetate Drugs 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
229940024606 amino acid Drugs 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
230000000259 anti-tumor effect Effects 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
238000007080 aromatic substitution reaction Methods 0.000 description 2
229940009098 aspartate Drugs 0.000 description 2
238000003556 assay Methods 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 2
230000008499 blood brain barrier function Effects 0.000 description 2
210000001218 blood-brain barrier Anatomy 0.000 description 2
150000001649 bromium compounds Chemical class 0.000 description 2
239000000872 buffer Substances 0.000 description 2
WUSOIHPNXFCZDU-UHFFFAOYSA-N butyl-(5-oxo-5-phenylmethoxy-2-phenylmethoxycarbonylpentyl)phosphinic acid Chemical compound C=1C=CC=CC=1COC(=O)C(CP(O)(=O)CCCC)CCC(=O)OCC1=CC=CC=C1 WUSOIHPNXFCZDU-UHFFFAOYSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
210000001175 cerebrospinal fluid Anatomy 0.000 description 2
DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 2
229960004316 cisplatin Drugs 0.000 description 2
239000002299 complementary DNA Substances 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
229960004397 cyclophosphamide Drugs 0.000 description 2
230000001085 cytostatic effect Effects 0.000 description 2
231100000433 cytotoxic Toxicity 0.000 description 2
230000001472 cytotoxic effect Effects 0.000 description 2
230000034994 death Effects 0.000 description 2
231100000517 death Toxicity 0.000 description 2
230000003247 decreasing effect Effects 0.000 description 2
UREBDLICKHMUKA-CXSFZGCWSA-N dexamethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O UREBDLICKHMUKA-CXSFZGCWSA-N 0.000 description 2
229960003957 dexamethasone Drugs 0.000 description 2
231100000673 dose–response relationship Toxicity 0.000 description 2
238000010828 elution Methods 0.000 description 2
210000000981 epithelium Anatomy 0.000 description 2
210000001035 gastrointestinal tract Anatomy 0.000 description 2
WHUUTDBJXJRKMK-VKHMYHEASA-L glutamate group Chemical group N[C@@H](CCC(=O)[O-])C(=O)[O-] WHUUTDBJXJRKMK-VKHMYHEASA-L 0.000 description 2
229960002913 goserelin Drugs 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
OSEXMMDMNNQLFC-UHFFFAOYSA-O hydroxy-oxo-(2-phenylethyl)phosphanium Chemical compound O[P+](=O)CCC1=CC=CC=C1 OSEXMMDMNNQLFC-UHFFFAOYSA-O 0.000 description 2
238000003384 imaging method Methods 0.000 description 2
239000007943 implant Substances 0.000 description 2
238000001727 in vivo Methods 0.000 description 2
230000002601 intratumoral effect Effects 0.000 description 2
238000007914 intraventricular administration Methods 0.000 description 2
150000004694 iodide salts Chemical class 0.000 description 2
229910052740 iodine Inorganic materials 0.000 description 2
210000003734 kidney Anatomy 0.000 description 2
210000003127 knee Anatomy 0.000 description 2
239000008101 lactose Substances 0.000 description 2
230000003902 lesion Effects 0.000 description 2
208000032839 leukemia Diseases 0.000 description 2
GFIJNRVAKGFPGQ-LIJARHBVSA-N leuprolide Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1N=CNC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 GFIJNRVAKGFPGQ-LIJARHBVSA-N 0.000 description 2
229960004338 leuprorelin Drugs 0.000 description 2
210000001165 lymph node Anatomy 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
230000003211 malignant effect Effects 0.000 description 2
208000026037 malignant tumor of neck Diseases 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
239000002609 medium Substances 0.000 description 2
208000010658 metastatic prostate carcinoma Diseases 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
235000010446 mineral oil Nutrition 0.000 description 2
238000002156 mixing Methods 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
230000001537 neural effect Effects 0.000 description 2
230000006959 non-competitive inhibition Effects 0.000 description 2
239000000346 nonvolatile oil Substances 0.000 description 2
HVFSJXUIRWUHRG-UHFFFAOYSA-N oic acid Natural products C1CC2C3CC=C4CC(OC5C(C(O)C(O)C(CO)O5)O)CC(O)C4(C)C3CCC2(C)C1C(C)C(O)CC(C)=C(C)C(=O)OC1OC(COC(C)=O)C(O)C(O)C1OC(C(C1O)O)OC(COC(C)=O)C1OC1OC(CO)C(O)C(O)C1O HVFSJXUIRWUHRG-UHFFFAOYSA-N 0.000 description 2
210000001672 ovary Anatomy 0.000 description 2
230000001575 pathological effect Effects 0.000 description 2
229940066842 petrolatum Drugs 0.000 description 2
239000000546 pharmaceutical excipient Substances 0.000 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
230000002980 postoperative effect Effects 0.000 description 2
230000002265 prevention Effects 0.000 description 2
230000008569 process Effects 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
210000005267 prostate cell Anatomy 0.000 description 2
208000021046 prostate intraepithelial neoplasia Diseases 0.000 description 2
210000004908 prostatic fluid Anatomy 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
230000002441 reversible effect Effects 0.000 description 2
238000012216 screening Methods 0.000 description 2
210000000582 semen Anatomy 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
229940006509 strontium-89 Drugs 0.000 description 2
CIOAGBVUUVVLOB-OUBTZVSYSA-N strontium-89 Chemical compound [89Sr] CIOAGBVUUVVLOB-OUBTZVSYSA-N 0.000 description 2
238000010254 subcutaneous injection Methods 0.000 description 2
239000007929 subcutaneous injection Substances 0.000 description 2
TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
125000000547 substituted alkyl group Chemical group 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000000758 substrate Substances 0.000 description 2
239000013589 supplement Substances 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
238000012353 t test Methods 0.000 description 2
239000003826 tablet Substances 0.000 description 2
229940104230 thymidine Drugs 0.000 description 2
230000002110 toxicologic effect Effects 0.000 description 2
231100000759 toxicological effect Toxicity 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
238000011277 treatment modality Methods 0.000 description 2
125000006493 trifluoromethyl benzyl group Chemical group 0.000 description 2
JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 2
230000006967 uncompetitive inhibition Effects 0.000 description 2
210000002700 urine Anatomy 0.000 description 2
DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
LSPHULWDVZXLIL-UHFFFAOYSA-N (+/-)-Camphoric acid Chemical compound CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
XMAYWYJOQHXEEK-OZXSUGGESA-N (2R,4S)-ketoconazole Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1OC[C@@H]1O[C@@](CN2C=NC=C2)(C=2C(=CC(Cl)=CC=2)Cl)OC1 XMAYWYJOQHXEEK-OZXSUGGESA-N 0.000 description 1
FELGMEQIXOGIFQ-CYBMUJFWSA-N (3r)-9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1h-carbazol-4-one Chemical compound CC1=NC=CN1C[C@@H]1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-CYBMUJFWSA-N 0.000 description 1
DEQANNDTNATYII-OULOTJBUSA-N (4r,7s,10s,13r,16s,19r)-10-(4-aminobutyl)-19-[[(2r)-2-amino-3-phenylpropanoyl]amino]-16-benzyl-n-[(2r,3r)-1,3-dihydroxybutan-2-yl]-7-[(1r)-1-hydroxyethyl]-13-(1h-indol-3-ylmethyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carboxa Chemical compound C([C@@H](N)C(=O)N[C@H]1CSSC[C@H](NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCCCN)NC(=O)[C@@H](CC=2C3=CC=CC=C3NC=2)NC(=O)[C@H](CC=2C=CC=CC=2)NC1=O)C(=O)N[C@H](CO)[C@H](O)C)C1=CC=CC=C1 DEQANNDTNATYII-OULOTJBUSA-N 0.000 description 1
PAMOVZQBFHPKDL-UHFFFAOYSA-N (5-oxo-5-phenylmethoxy-2-phenylmethoxycarbonylpentyl)-(3-phenylpropyl)phosphinic acid Chemical compound C=1C=CC=CC=1COC(=O)CCC(C(=O)OCC=1C=CC=CC=1)CP(=O)(O)CCCC1=CC=CC=C1 PAMOVZQBFHPKDL-UHFFFAOYSA-N 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical class CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
VUQPJRPDRDVQMN-UHFFFAOYSA-N 1-chlorooctadecane Chemical class CCCCCCCCCCCCCCCCCCCl VUQPJRPDRDVQMN-UHFFFAOYSA-N 0.000 description 1
VSNHCAURESNICA-NJFSPNSNSA-N 1-oxidanylurea Chemical compound N[14C](=O)NO VSNHCAURESNICA-NJFSPNSNSA-N 0.000 description 1
BFPYWIDHMRZLRN-UHFFFAOYSA-N 17alpha-ethynyl estradiol Natural products OC1=CC=C2C3CCC(C)(C(CC4)(O)C#C)C4C3CCC2=C1 BFPYWIDHMRZLRN-UHFFFAOYSA-N 0.000 description 1
WNVIEMRKZPPPOJ-UHFFFAOYSA-N 2-(1H-Indol-3-yl)propanoic acid Chemical compound C1=CC=C2C(C(C(O)=O)C)=CNC2=C1 WNVIEMRKZPPPOJ-UHFFFAOYSA-N 0.000 description 1
SOWXHUICOFYUDQ-UHFFFAOYSA-N 2-(1h-indol-2-yl)propanoic acid Chemical compound C1=CC=C2NC(C(C(O)=O)C)=CC2=C1 SOWXHUICOFYUDQ-UHFFFAOYSA-N 0.000 description 1
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
QXLQZLBNPTZMRK-UHFFFAOYSA-N 2-[(dimethylamino)methyl]-1-(2,4-dimethylphenyl)prop-2-en-1-one Chemical compound CN(C)CC(=C)C(=O)C1=CC=C(C)C=C1C QXLQZLBNPTZMRK-UHFFFAOYSA-N 0.000 description 1
TVGSTUGDPGIXPU-UHFFFAOYSA-N 2-[[benzyl(hydroxy)phosphoryl]amino]-2-(oxolan-2-yl)propanoic acid Chemical compound C1CCOC1C(C(O)=O)(C)NP(O)(=O)CC1=CC=CC=C1 TVGSTUGDPGIXPU-UHFFFAOYSA-N 0.000 description 1
GZASHIYXNBONPS-UHFFFAOYSA-N 2-[[hydroxy(3-naphthalen-2-ylpropyl)phosphoryl]methyl]pentanedioic acid Chemical compound C1=CC=CC2=CC(CCCP(O)(=O)CC(CCC(=O)O)C(O)=O)=CC=C21 GZASHIYXNBONPS-UHFFFAOYSA-N 0.000 description 1
VYTMVJAQFVBZGC-UHFFFAOYSA-N 2-[[hydroxy(3-pyridin-3-ylpropyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NP(O)(=O)CCCC1=CC=CN=C1 VYTMVJAQFVBZGC-UHFFFAOYSA-N 0.000 description 1
BLNYOCUDTHQLTD-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-(2,3,4-trimethoxyphenyl)acetic acid Chemical compound COC1=C(OC)C(OC)=CC=C1C(C(O)=O)OP(O)(=O)CC1=CC=CC=C1 BLNYOCUDTHQLTD-UHFFFAOYSA-N 0.000 description 1
HEJUEHZYMHFQPQ-UHFFFAOYSA-N 2-[benzyl(hydroxy)phosphoryl]oxy-2-(oxolan-2-yl)propanoic acid Chemical compound C1CCOC1C(C(O)=O)(C)OP(O)(=O)CC1=CC=CC=C1 HEJUEHZYMHFQPQ-UHFFFAOYSA-N 0.000 description 1
CVKMFSAVYPAZTQ-UHFFFAOYSA-N 2-methylhexanoic acid Chemical compound CCCCC(C)C(O)=O CVKMFSAVYPAZTQ-UHFFFAOYSA-N 0.000 description 1
CWNNYYIZGGDCHS-UHFFFAOYSA-N 2-methylideneglutaric acid Chemical compound OC(=O)CCC(=C)C(O)=O CWNNYYIZGGDCHS-UHFFFAOYSA-N 0.000 description 1
OVBFMEVBMNZIBR-UHFFFAOYSA-N 2-methylvaleric acid Chemical compound CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 1
229940080296 2-naphthalenesulfonate Drugs 0.000 description 1
125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 description 1
LEACJMVNYZDSKR-UHFFFAOYSA-N 2-octyldodecan-1-ol Chemical compound CCCCCCCCCCC(CO)CCCCCCCC LEACJMVNYZDSKR-UHFFFAOYSA-N 0.000 description 1
WMPPDTMATNBGJN-UHFFFAOYSA-N 2-phenylethylbromide Chemical class BrCCC1=CC=CC=C1 WMPPDTMATNBGJN-UHFFFAOYSA-N 0.000 description 1
KTKWUKAYWFMQSO-UHFFFAOYSA-N 2-thiophen-2-ylpropanoic acid Chemical compound OC(=O)C(C)C1=CC=CS1 KTKWUKAYWFMQSO-UHFFFAOYSA-N 0.000 description 1
MDHJHWOTXDVWRS-UHFFFAOYSA-N 2-thiophen-3-ylpropanoic acid Chemical compound OC(=O)C(C)C=1C=CSC=1 MDHJHWOTXDVWRS-UHFFFAOYSA-N 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
WUIABRMSWOKTOF-OYALTWQYSA-N 3-[[2-[2-[2-[[(2s,3r)-2-[[(2s,3s,4r)-4-[[(2s,3r)-2-[[6-amino-2-[(1s)-3-amino-1-[[(2s)-2,3-diamino-3-oxopropyl]amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[(2r,3s,4s,5s,6s)-3-[(2r,3s,4s,5r,6r)-4-carbamoyloxy-3,5-dihydroxy-6-(hydroxymethyl)ox Chemical compound OS([O-])(=O)=O.N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1NC=NC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C WUIABRMSWOKTOF-OYALTWQYSA-N 0.000 description 1
VCNINCPDXJGNHV-UHFFFAOYSA-N 3-[[hydroxy(3-thiophen-3-ylpropyl)phosphoryl]amino]pentanedioic acid Chemical compound OC(=O)CC(CC(O)=O)NP(O)(=O)CCCC=1C=CSC=1 VCNINCPDXJGNHV-UHFFFAOYSA-N 0.000 description 1
KASWLPVGGOTKBV-UHFFFAOYSA-N 3-[hydroxy-[3-(oxolan-2-yl)propyl]phosphoryl]-2-phenylpropanoic acid Chemical compound C=1C=CC=CC=1C(C(=O)O)CP(O)(=O)CCCC1CCCO1 KASWLPVGGOTKBV-UHFFFAOYSA-N 0.000 description 1
XMZQWZJMTBCUFT-UHFFFAOYSA-N 3-bromopropylbenzene Chemical compound BrCCCC1=CC=CC=C1 XMZQWZJMTBCUFT-UHFFFAOYSA-N 0.000 description 1
ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
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 description 1
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 description 1
KRJNISLOMXLLNV-UHFFFAOYSA-N 4-[[benzyl(hydroxy)phosphoryl]amino]-4-(oxolan-2-yl)pentanoic acid Chemical compound C1CCOC1C(CCC(O)=O)(C)NP(O)(=O)CC1=CC=CC=C1 KRJNISLOMXLLNV-UHFFFAOYSA-N 0.000 description 1
CVECLCXPEKUNQX-UHFFFAOYSA-N 4-[benzyl(hydroxy)phosphoryl]oxy-4-(oxolan-2-yl)butanoic acid Chemical compound C1CCOC1C(CCC(=O)O)OP(O)(=O)CC1=CC=CC=C1 CVECLCXPEKUNQX-UHFFFAOYSA-N 0.000 description 1
UCBMPVLZYWOMAM-UHFFFAOYSA-N 4-[benzyl(hydroxy)phosphoryl]oxy-4-(oxolan-2-yl)pentanoic acid Chemical compound C1CCOC1C(CCC(O)=O)(C)OP(O)(=O)CC1=CC=CC=C1 UCBMPVLZYWOMAM-UHFFFAOYSA-N 0.000 description 1
229960000549 4-dimethylaminophenol Drugs 0.000 description 1
WRSDJJXJDSEUSQ-UHFFFAOYSA-N 5-oxo-5-phenylmethoxypentanoic acid Chemical compound OC(=O)CCCC(=O)OCC1=CC=CC=C1 WRSDJJXJDSEUSQ-UHFFFAOYSA-N 0.000 description 1
FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
102100032187 Androgen receptor Human genes 0.000 description 1
208000031295 Animal disease Diseases 0.000 description 1
239000004475 Arginine Substances 0.000 description 1
108010024976 Asparaginase Proteins 0.000 description 1
102000015790 Asparaginase Human genes 0.000 description 1
DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 1
108010006654 Bleomycin Proteins 0.000 description 1
206010055113 Breast cancer metastatic Diseases 0.000 description 1
108010037003 Buserelin Proteins 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
RNPFAAQKINNIJX-UHFFFAOYSA-N C(CCC)C(C1=CC=CC=C1)P(O)(=O)OC Chemical compound C(CCC)C(C1=CC=CC=C1)P(O)(=O)OC RNPFAAQKINNIJX-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000282465 Canis Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
PTOAARAWEBMLNO-KVQBGUIXSA-N Cladribine Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@H]1C[C@H](O)[C@@H](CO)O1 PTOAARAWEBMLNO-KVQBGUIXSA-N 0.000 description 1
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
241000792859 Enema Species 0.000 description 1
RSEPBGGWRJCQGY-RBRWEJTLSA-N Estradiol valerate Chemical compound C1CC2=CC(O)=CC=C2[C@@H]2[C@@H]1[C@@H]1CC[C@H](OC(=O)CCCC)[C@@]1(C)CC2 RSEPBGGWRJCQGY-RBRWEJTLSA-N 0.000 description 1
DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 description 1
IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
BFPYWIDHMRZLRN-SLHNCBLASA-N Ethinyl estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 BFPYWIDHMRZLRN-SLHNCBLASA-N 0.000 description 1
DBVJJBKOTRCVKF-UHFFFAOYSA-N Etidronic acid Chemical compound OP(=O)(O)C(O)(C)P(O)(O)=O DBVJJBKOTRCVKF-UHFFFAOYSA-N 0.000 description 1
108010029961 Filgrastim Proteins 0.000 description 1
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
102100039619 Granulocyte colony-stimulating factor Human genes 0.000 description 1
102100039620 Granulocyte-macrophage colony-stimulating factor Human genes 0.000 description 1
101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
VSNHCAURESNICA-UHFFFAOYSA-N Hydroxyurea Chemical compound NC(=O)NO VSNHCAURESNICA-UHFFFAOYSA-N 0.000 description 1
XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 1
XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
108060003951 Immunoglobulin Proteins 0.000 description 1
102100040018 Interferon alpha-2 Human genes 0.000 description 1
108010079944 Interferon-alpha2b Proteins 0.000 description 1
108010050904 Interferons Proteins 0.000 description 1
102000014150 Interferons Human genes 0.000 description 1
ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
229930182816 L-glutamine Natural products 0.000 description 1
FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
206010050017 Lung cancer metastatic Diseases 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
229930195725 Mannitol Natural products 0.000 description 1
102000005741 Metalloproteases Human genes 0.000 description 1
108010006035 Metalloproteases Proteins 0.000 description 1
206010027480 Metastatic malignant melanoma Diseases 0.000 description 1
206010063569 Metastatic squamous cell carcinoma Diseases 0.000 description 1
206010068116 Metastatic uterine cancer Diseases 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
229930192392 Mitomycin Natural products 0.000 description 1
241000699660 Mus musculus Species 0.000 description 1
NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 1
108010090363 N-acetylaspartyl-beta-linked glutamate Proteins 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
206010029301 Neurological disorders of the eye Diseases 0.000 description 1
206010029350 Neurotoxicity Diseases 0.000 description 1
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 1
QUPGZWKXSBQKEE-UHFFFAOYSA-N OP(=O)CCCC1=CC=CC=C1 Chemical compound OP(=O)CCCC1=CC=CC=C1 QUPGZWKXSBQKEE-UHFFFAOYSA-N 0.000 description 1
108010016076 Octreotide Proteins 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
229930012538 Paclitaxel Natural products 0.000 description 1
CZYWHNTUXNGDGR-UHFFFAOYSA-L Pamidronate disodium Chemical compound O.O.O.O.O.[Na+].[Na+].NCCC(O)(P(O)([O-])=O)P(O)([O-])=O CZYWHNTUXNGDGR-UHFFFAOYSA-L 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 1
102000035195 Peptidases Human genes 0.000 description 1
108091005804 Peptidases Proteins 0.000 description 1
208000002151 Pleural effusion Diseases 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
241000283984 Rodentia Species 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
HVUMOYIDDBPOLL-XWVZOOPGSA-N Sorbitan monostearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O HVUMOYIDDBPOLL-XWVZOOPGSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
206010044221 Toxic encephalopathy Diseases 0.000 description 1
YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
206010064390 Tumour invasion Diseases 0.000 description 1
DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
230000009471 action Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
WNLRTRBMVRJNCN-UHFFFAOYSA-L adipate(2-) Chemical compound [O-]C(=O)CCCCC([O-])=O WNLRTRBMVRJNCN-UHFFFAOYSA-L 0.000 description 1
239000002671 adjuvant Substances 0.000 description 1
230000002411 adverse Effects 0.000 description 1
108700025316 aldesleukin Proteins 0.000 description 1
229960005310 aldesleukin Drugs 0.000 description 1
229940072056 alginate Drugs 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
125000004946 alkenylalkyl group Chemical group 0.000 description 1
125000003545 alkoxy group Chemical group 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
ROBVIMPUHSLWNV-UHFFFAOYSA-N aminoglutethimide Chemical compound C=1C=C(N)C=CC=1C1(CC)CCC(=O)NC1=O ROBVIMPUHSLWNV-UHFFFAOYSA-N 0.000 description 1
229960003437 aminoglutethimide Drugs 0.000 description 1
229910000148 ammonium phosphate Inorganic materials 0.000 description 1
235000019289 ammonium phosphates Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000003098 androgen Substances 0.000 description 1
108010080146 androgen receptors Proteins 0.000 description 1
238000009165 androgen replacement therapy Methods 0.000 description 1
238000005571 anion exchange chromatography Methods 0.000 description 1
230000003556 anti-epileptic effect Effects 0.000 description 1
230000000118 anti-neoplastic effect Effects 0.000 description 1
229940034982 antineoplastic agent Drugs 0.000 description 1
229940041181 antineoplastic drug Drugs 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
229960003272 asparaginase Drugs 0.000 description 1
DCXYFEDJOCDNAF-UHFFFAOYSA-M asparaginate Chemical compound [O-]C(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-M 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-L aspartate group Chemical group N[C@@H](CC(=O)[O-])C(=O)[O-] CKLJMWTZIZZHCS-REOHCLBHSA-L 0.000 description 1
VSRXQHXAPYXROS-UHFFFAOYSA-N azanide;cyclobutane-1,1-dicarboxylic acid;platinum(2+) Chemical compound [NH2-].[NH2-].[Pt+2].OC(=O)C1(C(O)=O)CCC1 VSRXQHXAPYXROS-UHFFFAOYSA-N 0.000 description 1
229960002255 azelaic acid Drugs 0.000 description 1
230000003385 bacteriostatic effect Effects 0.000 description 1
239000002585 base Substances 0.000 description 1
235000013871 bee wax Nutrition 0.000 description 1
239000012166 beeswax Substances 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
229940050390 benzoate Drugs 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
NVZRFUCVCIVKJR-UHFFFAOYSA-N benzyl(methoxy)phosphinic acid Chemical compound COP(O)(=O)CC1=CC=CC=C1 NVZRFUCVCIVKJR-UHFFFAOYSA-N 0.000 description 1
INANVXNIFVFBAR-UHFFFAOYSA-N benzyl(methyl)phosphinic acid Chemical compound CP(O)(=O)CC1=CC=CC=C1 INANVXNIFVFBAR-UHFFFAOYSA-N 0.000 description 1
OAXIRHXXAWQAFS-UHFFFAOYSA-N benzyl-(5-oxo-5-phenylmethoxy-2-phenylmethoxycarbonylpentyl)phosphinic acid Chemical compound C=1C=CC=CC=1CP(=O)(O)CC(C(=O)OCC=1C=CC=CC=1)CCC(=O)OCC1=CC=CC=C1 OAXIRHXXAWQAFS-UHFFFAOYSA-N 0.000 description 1
DMBLKETZCXYUQQ-UHFFFAOYSA-N benzyl-[(4-methylphenyl)methoxy]phosphinic acid Chemical compound C1=CC(C)=CC=C1COP(O)(=O)CC1=CC=CC=C1 DMBLKETZCXYUQQ-UHFFFAOYSA-N 0.000 description 1
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
PHIBEYMUALDAQI-UHFFFAOYSA-N benzylphosphinic acid Chemical compound OP(=O)CC1=CC=CC=C1 PHIBEYMUALDAQI-UHFFFAOYSA-N 0.000 description 1
230000000975 bioactive effect Effects 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
229960004395 bleomycin sulfate Drugs 0.000 description 1
230000037396 body weight Effects 0.000 description 1
CUWODFFVMXJOKD-UVLQAERKSA-N buserelin Chemical compound CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](COC(C)(C)C)NC(=O)[C@@H](NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H]1NC(=O)CC1)CC1=CC=C(O)C=C1 CUWODFFVMXJOKD-UVLQAERKSA-N 0.000 description 1
229960002719 buserelin Drugs 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
KVUAALJSMIVURS-ZEDZUCNESA-L calcium folinate Chemical compound [Ca+2].C1NC=2NC(N)=NC(=O)C=2N(C=O)C1CNC1=CC=C(C(=O)N[C@@H](CCC([O-])=O)C([O-])=O)C=C1 KVUAALJSMIVURS-ZEDZUCNESA-L 0.000 description 1
235000008207 calcium folinate Nutrition 0.000 description 1
239000011687 calcium folinate Substances 0.000 description 1
MIOPJNTWMNEORI-UHFFFAOYSA-N camphorsulfonic acid Chemical compound C1CC2(CS(O)(=O)=O)C(=O)CC1C2(C)C MIOPJNTWMNEORI-UHFFFAOYSA-N 0.000 description 1
230000009400 cancer invasion Effects 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
229960004562 carboplatin Drugs 0.000 description 1
229940111221 carmustine 100 mg Drugs 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
210000000170 cell membrane Anatomy 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
239000002738 chelating agent Substances 0.000 description 1
DQTRYXANLKJLPK-UHFFFAOYSA-N chlorophosphonous acid Chemical compound OP(O)Cl DQTRYXANLKJLPK-UHFFFAOYSA-N 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229910000151 chromium(III) phosphate Inorganic materials 0.000 description 1
IKZBVTPSNGOVRJ-UHFFFAOYSA-K chromium(iii) phosphate Chemical compound [Cr+3].[O-]P([O-])([O-])=O IKZBVTPSNGOVRJ-UHFFFAOYSA-K 0.000 description 1
229960002436 cladribine Drugs 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000003086 colorant Substances 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
230000001276 controlling effect Effects 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
239000006071 cream Substances 0.000 description 1
238000000315 cryotherapy Methods 0.000 description 1
238000009109 curative therapy Methods 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
UWFYSQMTEOIJJG-FDTZYFLXSA-N cyproterone acetate Chemical compound C1=C(Cl)C2=CC(=O)[C@@H]3C[C@@H]3[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(C)=O)(OC(=O)C)[C@@]1(C)CC2 UWFYSQMTEOIJJG-FDTZYFLXSA-N 0.000 description 1
229960000978 cyproterone acetate Drugs 0.000 description 1
229940034087 dacarbazine 100 mg Drugs 0.000 description 1
229960000975 daunorubicin Drugs 0.000 description 1
STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 description 1
125000002704 decyl group Chemical group [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])C([H])([H])C([H])([H])* 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
HCSDJECSMANTCX-UHFFFAOYSA-N dichloro(methoxy)phosphane Chemical compound COP(Cl)Cl HCSDJECSMANTCX-UHFFFAOYSA-N 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
RGLYKWWBQGJZGM-ISLYRVAYSA-N diethylstilbestrol Chemical compound C=1C=C(O)C=CC=1C(/CC)=C(\CC)C1=CC=C(O)C=C1 RGLYKWWBQGJZGM-ISLYRVAYSA-N 0.000 description 1
229960000452 diethylstilbestrol Drugs 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
125000003438 dodecyl group Chemical group [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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
229940043264 dodecyl sulfate Drugs 0.000 description 1
230000035622 drinking Effects 0.000 description 1
239000000890 drug combination Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000008387 emulsifying waxe Substances 0.000 description 1
239000007920 enema Substances 0.000 description 1
229940095399 enema Drugs 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
239000002532 enzyme inhibitor Substances 0.000 description 1
229940125532 enzyme inhibitor Drugs 0.000 description 1
210000002919 epithelial cell Anatomy 0.000 description 1
229960005309 estradiol Drugs 0.000 description 1
229930182833 estradiol Natural products 0.000 description 1
229960004766 estradiol valerate Drugs 0.000 description 1
229960004750 estramustine phosphate Drugs 0.000 description 1
ADFOJJHRTBFFOF-RBRWEJTLSA-N estramustine phosphate Chemical compound ClCCN(CCCl)C(=O)OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)OP(O)(O)=O)[C@@H]4[C@@H]3CCC2=C1 ADFOJJHRTBFFOF-RBRWEJTLSA-N 0.000 description 1
229940011871 estrogen Drugs 0.000 description 1
239000000262 estrogen Substances 0.000 description 1
229960003399 estrone Drugs 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
229960002568 ethinylestradiol Drugs 0.000 description 1
DEFVIWRASFVYLL-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl)tetraacetic acid Chemical compound OC(=O)CN(CC(O)=O)CCOCCOCCN(CC(O)=O)CC(O)=O DEFVIWRASFVYLL-UHFFFAOYSA-N 0.000 description 1
239000005038 ethylene vinyl acetate Substances 0.000 description 1
229940009626 etidronate Drugs 0.000 description 1
VJJPUSNTGOMMGY-MRVIYFEKSA-N etoposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 VJJPUSNTGOMMGY-MRVIYFEKSA-N 0.000 description 1
229960005420 etoposide Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000029142 excretion Effects 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
229960004177 filgrastim Drugs 0.000 description 1
239000010408 film Substances 0.000 description 1
238000009093 first-line therapy Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
229960000961 floxuridine Drugs 0.000 description 1
ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 description 1
229940116447 fludarabine phosphate 50 mg Drugs 0.000 description 1
MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 1
229960002074 flutamide Drugs 0.000 description 1
239000004088 foaming agent Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
230000000848 glutamatergic effect Effects 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-L glutarate(2-) Chemical compound [O-]C(=O)CCCC([O-])=O JFCQEDHGNNZCLN-UHFFFAOYSA-L 0.000 description 1
125000005456 glyceride group Chemical group 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
229960003607 granisetron hydrochloride Drugs 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
230000036541 health Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
239000003667 hormone antagonist Substances 0.000 description 1
BICAGYDGRXJYGD-UHFFFAOYSA-N hydrobromide;hydrochloride Chemical compound Cl.Br BICAGYDGRXJYGD-UHFFFAOYSA-N 0.000 description 1
239000000017 hydrogel Substances 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
QYZRTBKYBJRGJB-UHFFFAOYSA-N hydron;1-methyl-n-(9-methyl-9-azabicyclo[3.3.1]nonan-3-yl)indazole-3-carboxamide;chloride Chemical compound Cl.C1=CC=C2C(C(=O)NC3CC4CCCC(C3)N4C)=NN(C)C2=C1 QYZRTBKYBJRGJB-UHFFFAOYSA-N 0.000 description 1
229960001330 hydroxycarbamide Drugs 0.000 description 1
206010020718 hyperplasia Diseases 0.000 description 1
230000002390 hyperplastic effect Effects 0.000 description 1
229960000908 idarubicin Drugs 0.000 description 1
229960001101 ifosfamide Drugs 0.000 description 1
HOMGKSMUEGBAAB-UHFFFAOYSA-N ifosfamide Chemical compound ClCCNP1(=O)OCCCN1CCCl HOMGKSMUEGBAAB-UHFFFAOYSA-N 0.000 description 1
102000018358 immunoglobulin Human genes 0.000 description 1
238000009169 immunotherapy Methods 0.000 description 1
230000008676 import Effects 0.000 description 1
229940055742 indium-111 Drugs 0.000 description 1
APFVFJFRJDLVQX-AHCXROLUSA-N indium-111 Chemical compound [111In] APFVFJFRJDLVQX-AHCXROLUSA-N 0.000 description 1
229940079322 interferon Drugs 0.000 description 1
238000007917 intracranial administration Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
238000007913 intrathecal administration Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
229940110676 inzo Drugs 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical class II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
108010076560 isospaglumic acid Proteins 0.000 description 1
229960004125 ketoconazole Drugs 0.000 description 1
229960002293 leucovorin calcium Drugs 0.000 description 1
229940080464 levamisole 50 mg Drugs 0.000 description 1
230000002197 limbic effect Effects 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
201000007270 liver cancer Diseases 0.000 description 1
208000014018 liver neoplasm Diseases 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 1
OUTILEHLSPAZIN-UHFFFAOYSA-M magnesium;ethylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]CC1=CC=CC=C1 OUTILEHLSPAZIN-UHFFFAOYSA-M 0.000 description 1
SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
208000006178 malignant mesothelioma Diseases 0.000 description 1
201000005282 malignant pleural mesothelioma Diseases 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
108010082117 matrigel Proteins 0.000 description 1
229960001924 melphalan Drugs 0.000 description 1
SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 description 1
239000012528 membrane Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
239000002207 metabolite Substances 0.000 description 1
239000003475 metalloproteinase inhibitor Substances 0.000 description 1
208000021039 metastatic melanoma Diseases 0.000 description 1
229960000485 methotrexate Drugs 0.000 description 1
229940042472 mineral oil Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229960004857 mitomycin Drugs 0.000 description 1
229960001156 mitoxantrone Drugs 0.000 description 1
KKZJGLLVHKMTCM-UHFFFAOYSA-N mitoxantrone Chemical compound O=C1C2=C(O)C=CC(O)=C2C(=O)C2=C1C(NCCNCCO)=CC=C2NCCNCCO KKZJGLLVHKMTCM-UHFFFAOYSA-N 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
238000010369 molecular cloning Methods 0.000 description 1
125000001421 myristyl 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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
AEYWPRODWLOEFK-UHFFFAOYSA-N n-methylmethanamine;pyridine Chemical compound CNC.C1=CC=NC=C1 AEYWPRODWLOEFK-UHFFFAOYSA-N 0.000 description 1
KVBGVZZKJNLNJU-UHFFFAOYSA-M naphthalene-2-sulfonate Chemical compound C1=CC=CC2=CC(S(=O)(=O)[O-])=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-M 0.000 description 1
230000007135 neurotoxicity Effects 0.000 description 1
231100000228 neurotoxicity Toxicity 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
231100000344 non-irritating Toxicity 0.000 description 1
238000010899 nucleation Methods 0.000 description 1
238000011580 nude mouse model Methods 0.000 description 1
229960002700 octreotide Drugs 0.000 description 1
239000002674 ointment Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
229960005343 ondansetron Drugs 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
238000011474 orchiectomy Methods 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000002611 ovarian Effects 0.000 description 1
RQKYHDHLEMEVDR-UHFFFAOYSA-N oxo-bis(phenylmethoxy)phosphanium Chemical compound C=1C=CC=CC=1CO[P+](=O)OCC1=CC=CC=C1 RQKYHDHLEMEVDR-UHFFFAOYSA-N 0.000 description 1
229960001592 paclitaxel Drugs 0.000 description 1
238000002638 palliative care Methods 0.000 description 1
229960003978 pamidronic acid Drugs 0.000 description 1
208000004019 papillary adenocarcinoma Diseases 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
230000008506 pathogenesis Effects 0.000 description 1
230000037361 pathway Effects 0.000 description 1
229960001744 pegaspargase Drugs 0.000 description 1
108010001564 pegaspargase Proteins 0.000 description 1
229940049954 penicillin Drugs 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
230000002688 persistence Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
PTMHPRAIXMAOOB-UHFFFAOYSA-L phosphoramidate Chemical compound NP([O-])([O-])=O PTMHPRAIXMAOOB-UHFFFAOYSA-L 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920002338 polyhydroxyethylmethacrylate Polymers 0.000 description 1
239000001818 polyoxyethylene sorbitan monostearate Substances 0.000 description 1
235000010989 polyoxyethylene sorbitan monostearate Nutrition 0.000 description 1
229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229940113124 polysorbate 60 Drugs 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
OXCMYAYHXIHQOA-UHFFFAOYSA-N potassium;[2-butyl-5-chloro-3-[[4-[2-(1,2,4-triaza-3-azanidacyclopenta-1,4-dien-5-yl)phenyl]phenyl]methyl]imidazol-4-yl]methanol Chemical compound [K+].CCCCC1=NC(Cl)=C(CO)N1CC1=CC=C(C=2C(=CC=CC=2)C2=N[N-]N=N2)C=C1 OXCMYAYHXIHQOA-UHFFFAOYSA-N 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000002360 prefrontal effect Effects 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
230000035755 proliferation Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
235000019833 protease Nutrition 0.000 description 1
229940100618 rectal suppository Drugs 0.000 description 1
239000006215 rectal suppository Substances 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
229960002530 sargramostim Drugs 0.000 description 1
108010038379 sargramostim Proteins 0.000 description 1
230000000698 schizophrenic effect Effects 0.000 description 1
230000009291 secondary effect Effects 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
239000001587 sorbitan monostearate Substances 0.000 description 1
235000011076 sorbitan monostearate Nutrition 0.000 description 1
229940035048 sorbitan monostearate Drugs 0.000 description 1
GUCKKCMJTSNWCU-BQBZGAKWSA-N spaglumic acid Chemical compound CC(=O)N[C@H](C(O)=O)CC(=O)N[C@H](C(O)=O)CCC(O)=O GUCKKCMJTSNWCU-BQBZGAKWSA-N 0.000 description 1
229960000341 spaglumic acid Drugs 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
210000000278 spinal cord Anatomy 0.000 description 1
208000002320 spinal muscular atrophy Diseases 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
229960001052 streptozocin Drugs 0.000 description 1
ZSJLQEPLLKMAKR-GKHCUFPYSA-N streptozocin Chemical compound O=NN(C)C(=O)N[C@H]1[C@@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O ZSJLQEPLLKMAKR-GKHCUFPYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
230000009469 supplementation Effects 0.000 description 1
239000000829 suppository Substances 0.000 description 1
229960005314 suramin Drugs 0.000 description 1
FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
238000011477 surgical intervention Methods 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
210000002504 synaptic vesicle Anatomy 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
231100000057 systemic toxicity Toxicity 0.000 description 1
RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
NRUKOCRGYNPUPR-QBPJDGROSA-N teniposide Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@@H](OC[C@H]4O3)C=3SC=CC=3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 NRUKOCRGYNPUPR-QBPJDGROSA-N 0.000 description 1
229960001278 teniposide Drugs 0.000 description 1
210000001550 testis Anatomy 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
239000010409 thin film Substances 0.000 description 1
229940089635 thiotepa 15 mg Drugs 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
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
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
229960003048 vinblastine Drugs 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
JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound 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 JXLYSJRDGCGARV-XQKSVPLYSA-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
239000003871 white petrolatum Substances 0.000 description 1