EA035171B1 - Конъюгаты на основе связывающихся с psma лигандов или ингибиторов psma для позитронно-эмиссионной томографии - Google Patents
Конъюгаты на основе связывающихся с psma лигандов или ингибиторов psma для позитронно-эмиссионной томографии Download PDFInfo
- Publication number
- EA035171B1 EA035171B1 EA201690862A EA201690862A EA035171B1 EA 035171 B1 EA035171 B1 EA 035171B1 EA 201690862 A EA201690862 A EA 201690862A EA 201690862 A EA201690862 A EA 201690862A EA 035171 B1 EA035171 B1 EA 035171B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- formula
- conjugate according
- conjugate
- integer
- radionuclide
- Prior art date
Links
- 239000003446 ligand Substances 0.000 title claims abstract description 26
- 239000003112 inhibitor Substances 0.000 title claims abstract description 10
- 238000002600 positron emission tomography Methods 0.000 title abstract description 10
- 102100041003 Glutamate carboxypeptidase 2 Human genes 0.000 claims abstract description 57
- 101000892862 Homo sapiens Glutamate carboxypeptidase 2 Proteins 0.000 claims abstract description 56
- 229910052751 metal Inorganic materials 0.000 claims abstract description 33
- 239000002184 metal Substances 0.000 claims abstract description 33
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims abstract description 15
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000001959 radiotherapy Methods 0.000 claims abstract description 15
- 239000004472 Lysine Substances 0.000 claims abstract description 13
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims abstract description 11
- 235000003704 aspartic acid Nutrition 0.000 claims abstract description 11
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000004475 Arginine Substances 0.000 claims abstract description 8
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims abstract description 8
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229920001481 poly(stearyl methacrylate) Polymers 0.000 claims abstract 6
- 239000012634 fragment Substances 0.000 claims description 30
- 150000003839 salts Chemical class 0.000 claims description 27
- 229910021645 metal ion Inorganic materials 0.000 claims description 15
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 9
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims description 8
- 229920001184 polypeptide Polymers 0.000 claims description 8
- 229910052727 yttrium Inorganic materials 0.000 claims description 5
- 229910052765 Lutetium Inorganic materials 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 238000011362 radionuclide therapy Methods 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229910052701 rubidium Inorganic materials 0.000 claims description 2
- 229910052725 zinc Inorganic materials 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 229910052748 manganese Inorganic materials 0.000 claims 1
- 229910052719 titanium Inorganic materials 0.000 claims 1
- 229910052726 zirconium Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 80
- 239000000203 mixture Substances 0.000 abstract description 70
- 238000000034 method Methods 0.000 abstract description 56
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 37
- 201000010099 disease Diseases 0.000 abstract description 33
- 230000001717 pathogenic effect Effects 0.000 abstract description 19
- 230000008685 targeting Effects 0.000 abstract description 13
- 239000003795 chemical substances by application Substances 0.000 abstract description 10
- 239000012216 imaging agent Substances 0.000 abstract description 5
- 238000012544 monitoring process Methods 0.000 abstract 1
- 125000005647 linker group Chemical group 0.000 description 112
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 64
- -1 hydroxy, amino groups Chemical group 0.000 description 60
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 56
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 38
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 36
- 210000004027 cell Anatomy 0.000 description 35
- 239000000243 solution Substances 0.000 description 35
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- 125000000217 alkyl group Chemical group 0.000 description 32
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000011347 resin Substances 0.000 description 26
- 229920005989 resin Polymers 0.000 description 26
- 229910052796 boron Inorganic materials 0.000 description 23
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 22
- 206010028980 Neoplasm Diseases 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- 241001465754 Metazoa Species 0.000 description 20
- 229940024606 amino acid Drugs 0.000 description 19
- 235000001014 amino acid Nutrition 0.000 description 19
- 150000001413 amino acids Chemical class 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 18
- 201000011510 cancer Diseases 0.000 description 18
- 239000010949 copper Substances 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- 230000002285 radioactive effect Effects 0.000 description 17
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- 238000004128 high performance liquid chromatography Methods 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 125000000753 cycloalkyl group Chemical group 0.000 description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
- 125000004429 atom Chemical group 0.000 description 14
- 229910052739 hydrogen Inorganic materials 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- 125000003342 alkenyl group Chemical group 0.000 description 13
- 239000000969 carrier Substances 0.000 description 13
- 239000003085 diluting agent Substances 0.000 description 13
- 239000001257 hydrogen Substances 0.000 description 13
- 239000000546 pharmaceutical excipient Substances 0.000 description 13
- 239000000047 product Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000003710 aryl alkyl group Chemical group 0.000 description 12
- 125000004122 cyclic group Chemical group 0.000 description 12
- 239000003814 drug Substances 0.000 description 12
- 125000001072 heteroaryl group Chemical group 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 11
- 239000002253 acid Substances 0.000 description 11
- 125000000304 alkynyl group Chemical group 0.000 description 11
- 229910052786 argon Inorganic materials 0.000 description 11
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 11
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 11
- 239000008194 pharmaceutical composition Substances 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 210000001519 tissue Anatomy 0.000 description 11
- 125000002947 alkylene group Chemical group 0.000 description 10
- 125000004419 alkynylene group Chemical group 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 10
- 238000003384 imaging method Methods 0.000 description 10
- 239000012453 solvate Substances 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 9
- 238000012879 PET imaging Methods 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000004450 alkenylene group Chemical group 0.000 description 9
- 125000005518 carboxamido group Chemical group 0.000 description 9
- 125000000392 cycloalkenyl group Chemical group 0.000 description 9
- 235000018977 lysine Nutrition 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000009825 accumulation Methods 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 8
- 229960005261 aspartic acid Drugs 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 8
- 125000005842 heteroatom Chemical group 0.000 description 8
- 150000004677 hydrates Chemical class 0.000 description 8
- 208000027866 inflammatory disease Diseases 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000008186 active pharmaceutical agent Substances 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
- 238000001727 in vivo Methods 0.000 description 7
- CMWYAOXYQATXSI-UHFFFAOYSA-N n,n-dimethylformamide;piperidine Chemical compound CN(C)C=O.C1CCNCC1 CMWYAOXYQATXSI-UHFFFAOYSA-N 0.000 description 7
- 229960005190 phenylalanine Drugs 0.000 description 7
- 235000008729 phenylalanine Nutrition 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- 235000013877 carbamide Nutrition 0.000 description 6
- 239000013058 crude material Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 235000019439 ethyl acetate Nutrition 0.000 description 6
- 229910052736 halogen Inorganic materials 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 6
- 125000004404 heteroalkyl group Chemical group 0.000 description 6
- 150000002500 ions Chemical class 0.000 description 6
- 210000003734 kidney Anatomy 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 235000000346 sugar Nutrition 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 206010060862 Prostate cancer Diseases 0.000 description 5
- 208000000236 Prostatic Neoplasms Diseases 0.000 description 5
- 229960003121 arginine Drugs 0.000 description 5
- 235000009697 arginine Nutrition 0.000 description 5
- 239000000872 buffer Substances 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 238000003745 diagnosis Methods 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 235000013922 glutamic acid Nutrition 0.000 description 5
- 239000004220 glutamic acid Substances 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 238000002372 labelling Methods 0.000 description 5
- 238000004007 reversed phase HPLC Methods 0.000 description 5
- SOAPXKSPJAZNGO-WDSKDSINSA-N (2s)-2-[[(1s)-1,3-dicarboxypropyl]carbamoylamino]pentanedioic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)NC(=O)N[C@H](C(O)=O)CCC(O)=O SOAPXKSPJAZNGO-WDSKDSINSA-N 0.000 description 4
- JHALWMSZGCVVEM-UHFFFAOYSA-N 2-[4,7-bis(carboxymethyl)-1,4,7-triazonan-1-yl]acetic acid Chemical compound OC(=O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CC1 JHALWMSZGCVVEM-UHFFFAOYSA-N 0.000 description 4
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 239000012267 brine Substances 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000013522 chelant Substances 0.000 description 4
- 238000002591 computed tomography Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 238000003818 flash chromatography Methods 0.000 description 4
- 125000001188 haloalkyl group Chemical group 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 230000000877 morphologic effect Effects 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 229920000768 polyamine Polymers 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- 210000002307 prostate Anatomy 0.000 description 4
- 239000000941 radioactive substance Substances 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- 230000001954 sterilising effect Effects 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- SJVFAHZPLIXNDH-QFIPXVFZSA-N (2s)-2-(9h-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)OCC1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=CC=C1 SJVFAHZPLIXNDH-QFIPXVFZSA-N 0.000 description 3
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 3
- VVFZOMNABQROSQ-UHFFFAOYSA-N 5-o-benzyl 1-o-tert-butyl 2-[[1,5-bis[(2-methylpropan-2-yl)oxy]-1,5-dioxopentan-2-yl]carbamoylamino]pentanedioate Chemical compound CC(C)(C)OC(=O)CCC(C(=O)OC(C)(C)C)NC(=O)NC(C(=O)OC(C)(C)C)CCC(=O)OCC1=CC=CC=C1 VVFZOMNABQROSQ-UHFFFAOYSA-N 0.000 description 3
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
- 239000005695 Ammonium acetate Substances 0.000 description 3
- 229910004298 SiO 2 Inorganic materials 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 241000700605 Viruses Species 0.000 description 3
- 229910052782 aluminium Inorganic materials 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229940043376 ammonium acetate Drugs 0.000 description 3
- 235000019257 ammonium acetate Nutrition 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 150000003857 carboxamides Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 239000000032 diagnostic agent Substances 0.000 description 3
- 238000003682 fluorination reaction Methods 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- CKHJYUSOUQDYEN-UHFFFAOYSA-N gallium(3+) Chemical compound [Ga+3] CKHJYUSOUQDYEN-UHFFFAOYSA-N 0.000 description 3
- 229930195712 glutamate Natural products 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 229960003646 lysine Drugs 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 238000010647 peptide synthesis reaction Methods 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 238000002603 single-photon emission computed tomography Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 3
- 229940124597 therapeutic agent Drugs 0.000 description 3
- ZGYICYBLPGRURT-UHFFFAOYSA-N tri(propan-2-yl)silicon Chemical compound CC(C)[Si](C(C)C)C(C)C ZGYICYBLPGRURT-UHFFFAOYSA-N 0.000 description 3
- HNICLNKVURBTKV-NDEPHWFRSA-N (2s)-5-[[amino-[(2,2,4,6,7-pentamethyl-3h-1-benzofuran-5-yl)sulfonylamino]methylidene]amino]-2-(9h-fluoren-9-ylmethoxycarbonylamino)pentanoic acid Chemical compound C12=CC=CC=C2C2=CC=CC=C2C1COC(=O)N[C@H](C(O)=O)CCCN=C(N)NS(=O)(=O)C1=C(C)C(C)=C2OC(C)(C)CC2=C1C HNICLNKVURBTKV-NDEPHWFRSA-N 0.000 description 2
- NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- 125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- IRPGOXJVTQTAAN-UHFFFAOYSA-N 2,2,3,3,3-pentafluoropropanal Chemical compound FC(F)(F)C(F)(F)C=O IRPGOXJVTQTAAN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 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 2
- UQXNEWQGGVUVQA-UHFFFAOYSA-N 8-aminooctanoic acid Chemical compound NCCCCCCCC(O)=O UQXNEWQGGVUVQA-UHFFFAOYSA-N 0.000 description 2
- KLZUFWVZNOTSEM-UHFFFAOYSA-K Aluminum fluoride Inorganic materials F[Al](F)F KLZUFWVZNOTSEM-UHFFFAOYSA-K 0.000 description 2
- 229910018512 Al—OH Inorganic materials 0.000 description 2
- JQFZHHSQMKZLRU-IUCAKERBSA-N Arg-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CCCN=C(N)N JQFZHHSQMKZLRU-IUCAKERBSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 2
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 2
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 2
- 238000006646 Dess-Martin oxidation reaction Methods 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 241000283086 Equidae Species 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical group NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- ASNFTDCKZKHJSW-REOHCLBHSA-N Quisqualic acid Chemical compound OC(=O)[C@@H](N)CN1OC(=O)NC1=O ASNFTDCKZKHJSW-REOHCLBHSA-N 0.000 description 2
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 description 2
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical compound [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005094 alkyl carbonyl amino alkyl group Chemical group 0.000 description 2
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 description 2
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- CECABOMBVQNBEC-UHFFFAOYSA-K aluminium iodide Chemical compound I[Al](I)I CECABOMBVQNBEC-UHFFFAOYSA-K 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- 108010062796 arginyllysine Proteins 0.000 description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 210000000481 breast Anatomy 0.000 description 2
- 125000000837 carbohydrate group Chemical group 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 239000002738 chelating agent Substances 0.000 description 2
- 210000001072 colon Anatomy 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 description 2
- 229940039227 diagnostic agent Drugs 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229940014144 folate Drugs 0.000 description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 description 2
- 235000019152 folic acid Nutrition 0.000 description 2
- 239000011724 folic acid Substances 0.000 description 2
- 229930182830 galactose Natural products 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 238000007327 hydrogenolysis reaction Methods 0.000 description 2
- 150000002466 imines Chemical class 0.000 description 2
- 230000003834 intracellular effect Effects 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- OHSVLFRHMCKCQY-UHFFFAOYSA-N lutetium atom Chemical compound [Lu] OHSVLFRHMCKCQY-UHFFFAOYSA-N 0.000 description 2
- 210000002540 macrophage Anatomy 0.000 description 2
- 238000002595 magnetic resonance imaging Methods 0.000 description 2
- 230000003211 malignant effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002483 medication Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- FUFUQQWIXMPZFU-UHFFFAOYSA-N methyl 4-nitrophenylalaninate Chemical compound COC(=O)C(N)CC1=CC=C([N+]([O-])=O)C=C1 FUFUQQWIXMPZFU-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- IQZPDFORWZTSKT-UHFFFAOYSA-N nitrosulphonic acid Chemical class OS(=O)(=O)[N+]([O-])=O IQZPDFORWZTSKT-UHFFFAOYSA-N 0.000 description 2
- 229920001542 oligosaccharide Polymers 0.000 description 2
- 150000002482 oligosaccharides Chemical class 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 125000005702 oxyalkylene group Chemical group 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 210000000496 pancreas Anatomy 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 150000003214 pyranose derivatives Chemical class 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 238000006268 reductive amination reaction Methods 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 239000011669 selenium Substances 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 210000000813 small intestine Anatomy 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 238000000527 sonication Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 2
- QQWYQAQQADNEIC-RVDMUPIBSA-N tert-butyl [(z)-[cyano(phenyl)methylidene]amino] carbonate Chemical compound CC(C)(C)OC(=O)O\N=C(/C#N)C1=CC=CC=C1 QQWYQAQQADNEIC-RVDMUPIBSA-N 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 150000003852 triazoles Chemical group 0.000 description 2
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 210000003932 urinary bladder Anatomy 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- 238000012800 visualization Methods 0.000 description 2
- 102000035029 vitamin receptors Human genes 0.000 description 2
- 108091005463 vitamin receptors Proteins 0.000 description 2
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- YSSXJYWVWWFWMY-WHFBIAKZSA-N (2s)-2-[[(1r)-1-carboxy-2-sulfanylethyl]carbamoylamino]pentanedioic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)NC(=O)N[C@@H](CS)C(O)=O YSSXJYWVWWFWMY-WHFBIAKZSA-N 0.000 description 1
- PSLCKQYQNVNTQI-BHFSHLQUSA-N (2s)-2-aminobutanedioic acid;(2s)-2-aminopentanedioic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O.OC(=O)[C@@H](N)CCC(O)=O PSLCKQYQNVNTQI-BHFSHLQUSA-N 0.000 description 1
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 description 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- 150000000093 1,3-dioxanes Chemical class 0.000 description 1
- ITWBWJFEJCHKSN-UHFFFAOYSA-N 1,4,7-triazonane Chemical group C1CNCCNCCN1 ITWBWJFEJCHKSN-UHFFFAOYSA-N 0.000 description 1
- HNPMVNQYFPWBKI-UHFFFAOYSA-N 1,4,7-triazonane;trihydrochloride Chemical compound Cl.Cl.Cl.C1CNCCNCCN1 HNPMVNQYFPWBKI-UHFFFAOYSA-N 0.000 description 1
- 150000000094 1,4-dioxanes Chemical class 0.000 description 1
- VIRCVVBAAXBJEO-UHFFFAOYSA-N 1-(4-nitrophenyl)-3-(1,4,7-triazonan-1-yl)propan-2-amine Chemical compound C=1C=C([N+]([O-])=O)C=CC=1CC(N)CN1CCNCCNCC1 VIRCVVBAAXBJEO-UHFFFAOYSA-N 0.000 description 1
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Substances C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 1
- SOAPXKSPJAZNGO-UHFFFAOYSA-N 2-(1,3-dicarboxypropylcarbamoylamino)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)NC(=O)NC(C(O)=O)CCC(O)=O SOAPXKSPJAZNGO-UHFFFAOYSA-N 0.000 description 1
- VYHUGVOVCKRCKG-UHFFFAOYSA-N 2-(2-phenylethylsulfinylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CS(=O)CCC1=CC=CC=C1 VYHUGVOVCKRCKG-UHFFFAOYSA-N 0.000 description 1
- BFAYIORIWKEONN-UHFFFAOYSA-N 2-(2-phenylethylsulfonylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CS(=O)(=O)CCC1=CC=CC=C1 BFAYIORIWKEONN-UHFFFAOYSA-N 0.000 description 1
- JKMKVJHRNQTGPW-UHFFFAOYSA-N 2-(3-phenylpropylsulfinylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CS(=O)CCCC1=CC=CC=C1 JKMKVJHRNQTGPW-UHFFFAOYSA-N 0.000 description 1
- OTZATDKDOPYOAI-UHFFFAOYSA-N 2-(3-phenylpropylsulfonylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CS(=O)(=O)CCCC1=CC=CC=C1 OTZATDKDOPYOAI-UHFFFAOYSA-N 0.000 description 1
- VFPYZWRTUDAZGN-UHFFFAOYSA-N 2-(benzylsulfinylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CS(=O)CC1=CC=CC=C1 VFPYZWRTUDAZGN-UHFFFAOYSA-N 0.000 description 1
- FTDAIZALXRHAIP-UHFFFAOYSA-N 2-(benzylsulfonylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CS(=O)(=O)CC1=CC=CC=C1 FTDAIZALXRHAIP-UHFFFAOYSA-N 0.000 description 1
- UBPNBZGCZKGWIK-UHFFFAOYSA-N 2-(butylsulfinylmethyl)pentanedioic acid Chemical compound CCCCS(=O)CC(C(O)=O)CCC(O)=O UBPNBZGCZKGWIK-UHFFFAOYSA-N 0.000 description 1
- AQLGDVIEDOXUGY-UHFFFAOYSA-N 2-(butylsulfonylmethyl)pentanedioic acid Chemical compound CCCCS(=O)(=O)CC(C(O)=O)CCC(O)=O AQLGDVIEDOXUGY-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- NAWOQIXSDKDBEM-UHFFFAOYSA-N 2-(ethylsulfinylmethyl)pentanedioic acid Chemical compound CCS(=O)CC(C(O)=O)CCC(O)=O NAWOQIXSDKDBEM-UHFFFAOYSA-N 0.000 description 1
- SXSQDMPJGXEWGO-UHFFFAOYSA-N 2-(ethylsulfonylmethyl)pentanedioic acid Chemical compound CCS(=O)(=O)CC(C(O)=O)CCC(O)=O SXSQDMPJGXEWGO-UHFFFAOYSA-N 0.000 description 1
- YKJPKUXMGYHQKV-UHFFFAOYSA-N 2-(methylsulfinylmethyl)pentanedioic acid Chemical compound CS(=O)CC(C(O)=O)CCC(O)=O YKJPKUXMGYHQKV-UHFFFAOYSA-N 0.000 description 1
- KMOWMURCEKHBKW-UHFFFAOYSA-N 2-(methylsulfonylmethyl)pentanedioic acid Chemical compound CS(=O)(=O)CC(C(O)=O)CCC(O)=O KMOWMURCEKHBKW-UHFFFAOYSA-N 0.000 description 1
- GYGXSGJIYJXSFJ-UHFFFAOYSA-N 2-(propylsulfinylmethyl)pentanedioic acid Chemical compound CCCS(=O)CC(C(O)=O)CCC(O)=O GYGXSGJIYJXSFJ-UHFFFAOYSA-N 0.000 description 1
- NULDUARXSZRCAX-UHFFFAOYSA-N 2-(propylsulfonylmethyl)pentanedioic acid Chemical compound CCCS(=O)(=O)CC(C(O)=O)CCC(O)=O NULDUARXSZRCAX-UHFFFAOYSA-N 0.000 description 1
- CDALMBXQUMRRBP-UHFFFAOYSA-N 2-(pyridin-4-ylsulfinylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CS(=O)C1=CC=NC=C1 CDALMBXQUMRRBP-UHFFFAOYSA-N 0.000 description 1
- ORVBOXYBVFKIAM-UHFFFAOYSA-N 2-(pyridin-4-ylsulfonylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CS(=O)(=O)C1=CC=NC=C1 ORVBOXYBVFKIAM-UHFFFAOYSA-N 0.000 description 1
- UTWIARBFTRTHPR-UHFFFAOYSA-N 2-(sulfinylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C=S=O UTWIARBFTRTHPR-UHFFFAOYSA-N 0.000 description 1
- RHPCHKVYDYPCAJ-UHFFFAOYSA-N 2-(sulfonylmethyl)pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)C=S(=O)=O RHPCHKVYDYPCAJ-UHFFFAOYSA-N 0.000 description 1
- ABEIJMWLNYUWMD-KRWDZBQOSA-N 2-[(5s)-4,7-bis(carboxymethyl)-5-[(4-isothiocyanatophenyl)methyl]-1,4,7-triazonan-1-yl]acetic acid Chemical compound OC(=O)CN1CCN(CC(=O)O)CCN(CC(O)=O)C[C@@H]1CC1=CC=C(N=C=S)C=C1 ABEIJMWLNYUWMD-KRWDZBQOSA-N 0.000 description 1
- UYDHNYKGXODDAV-UHFFFAOYSA-N 2-[4-(carboxymethyl)-7-[2-(2,5-dioxopyrrolidin-1-yl)oxy-2-oxoethyl]-1,4,7-triazonan-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN(CC(O)=O)CCN1CC(=O)ON1C(=O)CCC1=O UYDHNYKGXODDAV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- 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 1
- 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 description 1
- YIXLYFSFJYJUBT-UHFFFAOYSA-N 2-[[hydroxy(3-phenylpentyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CCC(CC)C1=CC=CC=C1 YIXLYFSFJYJUBT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WATYBUNAXQXJTC-UHFFFAOYSA-N 2-[[hydroxy(4-phenylpentyl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)CCCC(C)C1=CC=CC=C1 WATYBUNAXQXJTC-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- VDCGGAXVFSYLTM-UHFFFAOYSA-N 2-[[hydroxy(oxan-2-yl)phosphoryl]methyl]pentanedioic acid Chemical compound OC(=O)CCC(C(O)=O)CP(O)(=O)C1CCCCO1 VDCGGAXVFSYLTM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- 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 description 1
- 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 description 1
- 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 1
- 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 1
- 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 description 1
- 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 description 1
- 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 1
- 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 1
- 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 description 1
- 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 description 1
- OZDAOHVKBFBBMZ-UHFFFAOYSA-N 2-aminopentanedioic acid;hydrate Chemical compound O.OC(=O)C(N)CCC(O)=O OZDAOHVKBFBBMZ-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- KBDDHSXZOLZZGF-UHFFFAOYSA-N 4-[[1,5-bis[(2-methylpropan-2-yl)oxy]-1,5-dioxopentan-2-yl]carbamoylamino]-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid Chemical compound CC(C)(C)OC(=O)CCC(C(=O)OC(C)(C)C)NC(=O)NC(CCC(O)=O)C(=O)OC(C)(C)C KBDDHSXZOLZZGF-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- 206010069754 Acquired gene mutation Diseases 0.000 description 1
- HJVGMOYJDDXLMI-AVGNSLFASA-N Arg-Arg-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@@H](N)CCCNC(N)=N HJVGMOYJDDXLMI-AVGNSLFASA-N 0.000 description 1
- XVLLUZMFSAYKJV-GUBZILKMSA-N Arg-Asp-Arg Chemical compound NC(N)=NCCC[C@H](N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCN=C(N)N)C(O)=O XVLLUZMFSAYKJV-GUBZILKMSA-N 0.000 description 1
- SDHFVYLZFBDSQT-DCAQKATOSA-N Asp-Arg-Lys Chemical compound C(CCN)C[C@@H](C(=O)O)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(=O)O)N SDHFVYLZFBDSQT-DCAQKATOSA-N 0.000 description 1
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- 208000011691 Burkitt lymphomas Diseases 0.000 description 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 108010001857 Cell Surface Receptors Proteins 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 241000283153 Cetacea Species 0.000 description 1
- 102000005853 Clathrin Human genes 0.000 description 1
- 108010019874 Clathrin Proteins 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 1
- 241001125840 Coryphaenidae Species 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- ASNFTDCKZKHJSW-UHFFFAOYSA-N DL-Quisqualic acid Natural products OC(=O)C(N)CN1OC(=O)NC1=O ASNFTDCKZKHJSW-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 208000005189 Embolism Diseases 0.000 description 1
- 101710181478 Envelope glycoprotein GP350 Proteins 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 208000001640 Fibromyalgia Diseases 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 241000282818 Giraffidae Species 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- KOSRFJWDECSPRO-WDSKDSINSA-N Glu-Glu Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(O)=O KOSRFJWDECSPRO-WDSKDSINSA-N 0.000 description 1
- IEFJWDNGDZAYNZ-BYPYZUCNSA-N Gly-Glu Chemical compound NCC(=O)N[C@H](C(O)=O)CCC(O)=O IEFJWDNGDZAYNZ-BYPYZUCNSA-N 0.000 description 1
- 241000282575 Gorilla Species 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- 208000017604 Hodgkin disease Diseases 0.000 description 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 1
- 208000008839 Kidney Neoplasms Diseases 0.000 description 1
- OYIFNHCXNCRBQI-BYPYZUCNSA-N L-2-aminoadipic acid Chemical compound OC(=O)[C@@H](N)CCCC(O)=O OYIFNHCXNCRBQI-BYPYZUCNSA-N 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- 235000019766 L-Lysine Nutrition 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- 229930195714 L-glutamate Natural products 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
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 1
- 125000002435 L-phenylalanyl group Chemical group O=C([*])[C@](N([H])[H])([H])C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 206010025323 Lymphomas Diseases 0.000 description 1
- 101710141452 Major surface glycoprotein G Proteins 0.000 description 1
- 206010027406 Mesothelioma Diseases 0.000 description 1
- 239000012901 Milli-Q water Substances 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 101100059320 Mus musculus Ccdc85b gene Proteins 0.000 description 1
- 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 1
- 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 1
- 108010002311 N-glycylglutamic acid Proteins 0.000 description 1
- 208000002454 Nasopharyngeal Carcinoma Diseases 0.000 description 1
- 206010031252 Osteomyelitis Diseases 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- 208000025174 PANDAS Diseases 0.000 description 1
- 208000021155 Paediatric autoimmune neuropsychiatric disorders associated with streptococcal infection Diseases 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 241000282579 Pan Species 0.000 description 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 description 1
- 240000000220 Panda oleosa Species 0.000 description 1
- 235000016496 Panda oleosa Nutrition 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 241000282373 Panthera pardus Species 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- VHWOBXIWBDWZHK-IHRRRGAJSA-N Phe-Arg-Asp Chemical compound NC(N)=NCCC[C@@H](C(=O)N[C@@H](CC(O)=O)C(O)=O)NC(=O)[C@@H](N)CC1=CC=CC=C1 VHWOBXIWBDWZHK-IHRRRGAJSA-N 0.000 description 1
- OXKJSGGTHFMGDT-UFYCRDLUSA-N Phe-Phe-Arg Chemical compound C([C@H](N)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C1=CC=CC=C1 OXKJSGGTHFMGDT-UFYCRDLUSA-N 0.000 description 1
- 206010035226 Plasma cell myeloma Diseases 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 241000283080 Proboscidea <mammal> Species 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 208000034189 Sclerosis Diseases 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 208000021386 Sjogren Syndrome Diseases 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 1
- 239000004473 Threonine Substances 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 241000282458 Ursus sp. Species 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- LFEYMWCCUAOUKZ-FVGYRXGTSA-N [(2s)-1,5-bis[(2-methylpropan-2-yl)oxy]-1,5-dioxopentan-2-yl]azanium;chloride Chemical compound Cl.CC(C)(C)OC(=O)CC[C@H](N)C(=O)OC(C)(C)C LFEYMWCCUAOUKZ-FVGYRXGTSA-N 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 125000005262 alkoxyamine group Chemical group 0.000 description 1
- 125000006356 alkylene carbonyl group Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- KOSRFJWDECSPRO-UHFFFAOYSA-N alpha-L-glutamyl-L-glutamic acid Natural products OC(=O)CCC(N)C(=O)NC(CCC(O)=O)C(O)=O KOSRFJWDECSPRO-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000012300 argon atmosphere Substances 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 235000009582 asparagine Nutrition 0.000 description 1
- 229960001230 asparagine Drugs 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 239000000090 biomarker Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 1
- 125000005620 boronic acid group Chemical class 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 210000003679 cervix uteri Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 208000037976 chronic inflammation Diseases 0.000 description 1
- 230000006020 chronic inflammation Effects 0.000 description 1
- 229930193282 clathrin Natural products 0.000 description 1
- 208000029742 colonic neoplasm Diseases 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 150000001924 cycloalkanes Chemical class 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000005356 cycloalkylalkenyl group Chemical group 0.000 description 1
- 125000002993 cycloalkylene group Chemical group 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
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 150000008266 deoxy sugars Chemical class 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000009977 dual effect Effects 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 210000003372 endocrine gland Anatomy 0.000 description 1
- 210000003238 esophagus Anatomy 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000012025 fluorinating agent Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000002599 functional magnetic resonance imaging Methods 0.000 description 1
- OWQDWQKWSLFFFR-WDSKDSINSA-N gamma-Glu-Glu Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@H](C(O)=O)CCC(O)=O OWQDWQKWSLFFFR-WDSKDSINSA-N 0.000 description 1
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 1
- 108010055341 glutamyl-glutamic acid Proteins 0.000 description 1
- 150000004676 glycans Chemical class 0.000 description 1
- 208000024908 graft versus host disease Diseases 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 210000003128 head Anatomy 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 210000004969 inflammatory cell Anatomy 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 description 1
- 229960000310 isoleucine Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 210000000867 larynx Anatomy 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 208000014018 liver neoplasm Diseases 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 208000020816 lung neoplasm Diseases 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 210000003712 lysosome Anatomy 0.000 description 1
- 230000001868 lysosomic effect Effects 0.000 description 1
- 210000000260 male genitalia Anatomy 0.000 description 1
- 210000001161 mammalian embryo Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 102000006240 membrane receptors Human genes 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 210000001616 monocyte Anatomy 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 201000000050 myeloid neoplasm Diseases 0.000 description 1
- SJYQYOVTHISIKX-UHFFFAOYSA-N n,n-dimethylformamide;n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CN(C)C=O.CCN(C(C)C)C(C)C SJYQYOVTHISIKX-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100001222 nononcogenic Toxicity 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 231100000590 oncogenic Toxicity 0.000 description 1
- 230000002246 oncogenic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- JFCQEDHGNNZCLN-MABBKULESA-N pentanedioic acid Chemical class O[14C](=O)CCC[14C](O)=O JFCQEDHGNNZCLN-MABBKULESA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002994 phenylalanines Chemical class 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- 238000012636 positron electron tomography Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 208000023958 prostate neoplasm Diseases 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000003439 radiotherapeutic effect Effects 0.000 description 1
- 239000012048 reactive intermediate Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 210000000664 rectum Anatomy 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 210000003079 salivary gland Anatomy 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 150000003349 semicarbazides Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 210000003491 skin Anatomy 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- 230000037439 somatic mutation Effects 0.000 description 1
- 208000020431 spinal cord injury Diseases 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000626 sulfinic acid group Chemical group 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000004963 sulfonylalkyl group Chemical group 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 210000001550 testis Anatomy 0.000 description 1
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 231100000440 toxicity profile Toxicity 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 210000004291 uterus Anatomy 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
- GBNDTYKAOXLLID-UHFFFAOYSA-N zirconium(4+) ion Chemical compound [Zr+4] GBNDTYKAOXLLID-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0497—Organic compounds conjugates with a carrier being an organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/041—Heterocyclic compounds
- A61K51/044—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins
- A61K51/0459—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine, rifamycins having six-membered rings with two nitrogen atoms as the only ring hetero atoms, e.g. piperazine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0474—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group
- A61K51/0482—Organic compounds complexes or complex-forming compounds, i.e. wherein a radioactive metal (e.g. 111In3+) is complexed or chelated by, e.g. a N2S2, N3S, NS3, N4 chelating group chelates from cyclic ligands, e.g. DOTA
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/52—Use of compounds or compositions for colorimetric, spectrophotometric or fluorometric investigation, e.g. use of reagent paper and including single- and multilayer analytical elements
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/60—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances involving radioactive labelled substances
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N2800/00—Detection or diagnosis of diseases
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Optics & Photonics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Hematology (AREA)
- Immunology (AREA)
- Urology & Nephrology (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Cell Biology (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Food Science & Technology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicinal Preparation (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nuclear Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361904387P | 2013-11-14 | 2013-11-14 | |
| US201361904400P | 2013-11-14 | 2013-11-14 | |
| US201361909822P | 2013-11-27 | 2013-11-27 | |
| PCT/US2014/065467 WO2015073678A1 (en) | 2013-11-14 | 2014-11-13 | Compounds for positron emission tomography |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201690862A1 EA201690862A1 (ru) | 2016-12-30 |
| EA035171B1 true EA035171B1 (ru) | 2020-05-08 |
Family
ID=53058011
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201690862A EA035171B1 (ru) | 2013-11-14 | 2014-11-13 | Конъюгаты на основе связывающихся с psma лигандов или ингибиторов psma для позитронно-эмиссионной томографии |
Country Status (15)
| Country | Link |
|---|---|
| US (4) | US20160287731A1 (https=) |
| EP (4) | EP3069147A4 (https=) |
| JP (6) | JP6464166B2 (https=) |
| KR (1) | KR102457827B1 (https=) |
| CN (2) | CN105849568B (https=) |
| AU (4) | AU2014348601A1 (https=) |
| BR (1) | BR112016010927A2 (https=) |
| CA (1) | CA2930581A1 (https=) |
| EA (1) | EA035171B1 (https=) |
| ES (1) | ES3013992T3 (https=) |
| IL (2) | IL245612A0 (https=) |
| MX (2) | MX2016006219A (https=) |
| SG (1) | SG10201803618RA (https=) |
| TW (1) | TWI657827B (https=) |
| WO (1) | WO2015073678A1 (https=) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4464384A3 (en) | 2007-08-17 | 2025-01-08 | Purdue Research Foundation | Psma binding ligand-linker conjugates and methods for using |
| US9951324B2 (en) | 2010-02-25 | 2018-04-24 | Purdue Research Foundation | PSMA binding ligand-linker conjugates and methods for using |
| BR112015011118B1 (pt) | 2012-11-15 | 2022-12-13 | Endocyte, Inc | Conjugado; composição farmacêutica; e uso de um conjugado |
| LT4095130T (lt) | 2013-10-18 | 2024-04-25 | Novartis Ag | Žymėti prostatos specifinio membranos antigeno (psma) inhibitoriai, jų naudojimas kaip vizualizavimo medžiagų ir farmacinių medžiagų prostatos vėžiui gydyti |
| BR112016010927A2 (pt) | 2013-11-14 | 2017-08-08 | Endocyte Inc | Conjugado de fórmula |
| US10188759B2 (en) | 2015-01-07 | 2019-01-29 | Endocyte, Inc. | Conjugates for imaging |
| AU2016333334B2 (en) | 2015-09-30 | 2019-07-25 | Deutsches Krebsforschungszentrum | 18F-tagged inhibitors of prostate specific membrane antigen (PSMA) and their use as imaging agents for prostate cancer |
| US10688200B2 (en) * | 2015-12-31 | 2020-06-23 | Five Eleven Pharma Inc. | Urea-based prostate specific membrane antigen (PSMA) inhibitors for imaging and therapy |
| WO2017117687A1 (en) | 2016-01-10 | 2017-07-13 | British Columbia Cancer Agency Branch | 18/19f-labelled compounds which target the prostate specific membrane antigen |
| EP3493855A4 (en) | 2016-08-02 | 2020-04-01 | ISI Life Sciences, Inc. | COMPOSITIONS AND METHOD FOR DETECTING CANCER CELLS IN A TISSUE SAMPLE |
| WO2018026538A1 (en) * | 2016-08-02 | 2018-02-08 | ISI Life Sciences Inc. | Novel scaffolds for intracellular compound delivery for the detection of cancer cells |
| US10239891B2 (en) | 2017-05-15 | 2019-03-26 | Indicator Systems International, Inc. | Compositions to detect remnant cancer cells |
| BR112019002560B1 (pt) | 2016-08-10 | 2022-08-16 | Cancer Targeted Technology Llc | Composto, composição farmacêutica, seus usos e método de preparação do mesmo |
| EP3544960A1 (en) * | 2016-11-23 | 2019-10-02 | Cancer Targeted Technology LLC | Albumin-binding psma inhibitors |
| CN106632341A (zh) * | 2016-12-27 | 2017-05-10 | 天津阿尔塔科技有限公司 | 一种d‑叶酸的合成方法 |
| US10753942B2 (en) | 2017-05-15 | 2020-08-25 | Indicator Systems International, Inc. | Methods to detect remnant cancer cells |
| US12208102B2 (en) | 2018-04-17 | 2025-01-28 | Endocyte, Inc. | Methods of treating cancer |
| WO2019246445A1 (en) * | 2018-06-20 | 2019-12-26 | The Research Foundation For The State University Of New York | Triazamacrocycle-derived chelator compositions for coordination of imaging and therapy metal ions and methods of using same |
| CN108997170B (zh) * | 2018-08-07 | 2021-04-06 | 贾国苓 | 一种易碱解多羧基螯合物及其制备工艺 |
| WO2020108753A1 (en) * | 2018-11-28 | 2020-06-04 | ITM Isotopen Technologien München AG | Novel tumor antigen binding agents and uses thereof |
| WO2020165409A1 (en) * | 2019-02-14 | 2020-08-20 | Deutsches Krebsforschungszentrum | Prostate specific membrane antigen (psma) ligands comprising an amylase cleavable linker |
| WO2020210909A1 (en) | 2019-04-17 | 2020-10-22 | Provincial Health Services Authority | Novel radiolabelled compounds for diagnosis or treatment of prostate-specific membrane antigen-expressing cancer |
| CN114096264B (zh) | 2019-05-20 | 2025-03-14 | 因多塞特股份有限公司 | 制备psma缀合物的方法 |
| CN114401947B (zh) | 2019-06-21 | 2024-11-29 | 省卫生服务机构 | 靶向前列腺特异性膜抗原的放射性标记化合物 |
| CN110627837A (zh) * | 2019-09-10 | 2019-12-31 | 齐鲁工业大学 | 一种检测一氧化碳的金属有机框架材料及制备方法和应用 |
| WO2022006007A1 (en) * | 2020-06-29 | 2022-01-06 | The General Hospital Corporation | Methods for imaging bacterial infections |
| CN114377017A (zh) * | 2020-10-21 | 2022-04-22 | 复旦大学 | 叶酸和叶酸修饰在诱导B细胞免疫耐受和靶向mIgM阳性表达的B细胞淋巴瘤中的用途 |
| TW202241516A (zh) * | 2020-12-17 | 2022-11-01 | 美商杜夫特學院信託管理公司 | 經fap活化之放射性治療診斷(radiotheranostics)，與其相關用途 |
| EP4308550A4 (en) * | 2021-03-19 | 2025-04-23 | The Hong Kong Polytechnic University | Chiral tacn/nota compounds/derivatives with and without metals for application |
| US20240228524A1 (en) * | 2021-03-20 | 2024-07-11 | The Research Foundation For The State University Of New York | Iron(iii) macrocyclic complexes with mixed hyroxyl pendants as mri contrast agents |
| IL307499A (en) * | 2021-04-16 | 2023-12-01 | Novartis Ag | Folate receptor-targeted radiotherapeutic agents and their use |
| CN114028590B (zh) * | 2021-11-18 | 2022-09-06 | 北京大学 | 颗粒酶b靶向配合物、放射性药物及其制备方法和应用 |
| CN116375709B (zh) * | 2021-12-30 | 2025-11-07 | 南京江原安迪科正电子研究发展有限公司 | 一种叶酸受体靶向药物、金属络合物及其制备方法与用途 |
| KR20240151845A (ko) * | 2022-02-24 | 2024-10-18 | 퍼듀 리서치 파운데이션 | 하이드록시아파타이트-표적화 영상화 및 요법을 위한 접합체, 조성물, 및 방법 |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7399460B2 (en) * | 1998-05-16 | 2008-07-15 | Bracco International B.V. | Metal complexes derivatized with folate for use in diagnostic and therapeutic applications |
| US20090214636A1 (en) * | 2005-07-05 | 2009-08-27 | Low Philip S | Imaging and Therapeutic Method Using Monocytes |
| US20120009121A1 (en) * | 2009-03-19 | 2012-01-12 | The Johns Hopkins University | Psma-targeting compounds and uses thereof |
| US20120322741A1 (en) * | 2010-02-25 | 2012-12-20 | Purdue Research Foundation | Psma binding ligand-linker conjugates and methods for using |
Family Cites Families (266)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4713249A (en) | 1981-11-12 | 1987-12-15 | Schroeder Ulf | Crystallized carbohydrate matrix for biologically active substances, a process of preparing said matrix, and the use thereof |
| EP0116208B1 (en) | 1982-12-07 | 1988-03-30 | Kyowa Hakko Kogyo Co., Ltd. | Mitomycin analogues |
| JPS60255789A (ja) | 1984-06-01 | 1985-12-17 | Kyowa Hakko Kogyo Co Ltd | マイトマイシン誘導体，その製造法および抗腫瘍剤 |
| US5266333A (en) | 1985-03-06 | 1993-11-30 | American Cyanamid Company | Water dispersible and water soluble carbohydrate polymer compositions for parenteral administration of growth hormone |
| US5103018A (en) | 1986-08-26 | 1992-04-07 | Kyowa Hakko Kogyo Kabushiki Kaisha | Mitomycin derivatives |
| CA2044590A1 (en) | 1989-11-13 | 1991-05-14 | Marc D. Better | Chimeric mouse-human a10 antibody with specificity to a human tumor cell antigen |
| US5627165A (en) | 1990-06-13 | 1997-05-06 | Drug Innovation & Design, Inc. | Phosphorous prodrugs and therapeutic delivery systems using same |
| AU653565B2 (en) | 1990-12-21 | 1994-10-06 | Nikken Corporation | Raw sewage disposal apparatus and prefab for accomodating the same |
| US6291196B1 (en) | 1992-01-31 | 2001-09-18 | Research Corporation Technologies, Inc. | Melanoma and prostate cancer specific antibodies for immunodetection and immunotherapy |
| US7070782B1 (en) | 1992-11-05 | 2006-07-04 | Sloan-Kettering Institute For Cancer Research | Prostate-specific membrane antigen |
| US5674977A (en) | 1993-02-05 | 1997-10-07 | The Ontario Cancer Institute | Branched synthetic peptide conjugate |
| US6569432B1 (en) | 1995-02-24 | 2003-05-27 | Sloan-Kettering Institute For Cancer Research | Prostate-specific membrane antigen and uses thereof |
| JP3538221B2 (ja) | 1993-11-19 | 2004-06-14 | 富士写真フイルム株式会社 | 定着濃厚液およびそれを用いたハロゲン化銀写真感光材料の処理方法 |
| US5417982A (en) | 1994-02-17 | 1995-05-23 | Modi; Pankaj | Controlled release of drugs or hormones in biodegradable polymer microspheres |
| US5866679A (en) | 1994-06-28 | 1999-02-02 | Merck & Co., Inc. | Peptides |
| US6946133B1 (en) | 1996-03-20 | 2005-09-20 | The United States Of America As Represented By The Department Of Health And Human Services | Prostate specific antigen oligo-epitope peptide |
| AU726914B2 (en) | 1996-04-01 | 2000-11-23 | Epix Pharmaceuticals, Inc. | Bioactivated diagnostic imaging contrast agents |
| CA2251186A1 (en) | 1996-04-05 | 1997-10-16 | The Johns Hopkins University | A method of enriching rare cells |
| US5795877A (en) | 1996-12-31 | 1998-08-18 | Guilford Pharmaceuticals Inc. | Inhibitors of NAALADase enzyme activity |
| US6054444A (en) | 1997-04-24 | 2000-04-25 | Guilford Pharmaceuticals Inc. | Phosphonic acid derivatives |
| US5672592A (en) | 1996-06-17 | 1997-09-30 | Guilford Pharmaceuticals Inc. | Certain phosphonomethyl-pentanedioic acid derivatives thereof |
| US5902817A (en) | 1997-04-09 | 1999-05-11 | Guilford Pharmaceuticals Inc. | Certain sulfoxide and sulfone derivatives |
| US5863536A (en) | 1996-12-31 | 1999-01-26 | Guilford Pharmaceuticals Inc. | Phosphoramidate derivatives |
| US5998362A (en) | 1996-09-12 | 1999-12-07 | Merck & Co., Inc. | Conjugates useful in the treatment of prostate cancer |
| US6368598B1 (en) | 1996-09-16 | 2002-04-09 | Jcrt Radiation Oncology Support Services, Inc. | Drug complex for treatment of metastatic prostate cancer |
| US5962521A (en) | 1997-04-04 | 1999-10-05 | Guilford Pharmaceuticals Inc. | Hydroxamic acid derivatives |
| US6177404B1 (en) | 1996-10-15 | 2001-01-23 | Merck & Co., Inc. | Conjugates useful in the treatment of benign prostatic hyperplasia |
| US5948750A (en) | 1996-10-30 | 1999-09-07 | Merck & Co., Inc. | Conjugates useful in the treatment of prostate cancer |
| JP3981416B2 (ja) | 1997-04-10 | 2007-09-26 | ユニバーシティ メディカル センター ナイメーヘン | Ｐｃａ３タンパク質、ｐｃａ３遺伝子、及びこれらの用途 |
| US6127333A (en) | 1997-07-10 | 2000-10-03 | Merck & Co., Inc. | Conjugates useful in the treatment of prostate cancer |
| US6391305B1 (en) | 1997-09-10 | 2002-05-21 | Merck & Co., Inc. | Conjugates useful in the treatment of prostate cancer |
| US20020115596A1 (en) | 1997-10-27 | 2002-08-22 | Merk & Co., Inc. | Conjugates useful in the treatment of prostate cancer |
| ZA9810974B (en) | 1997-12-02 | 1999-06-03 | Merck & Co Inc | Conjugates useful in the treatment of prostate cancer |
| HRP20000367A2 (en) | 1997-12-02 | 2000-12-31 | Merck & Co Inc | Conjugates useful in the treatment of prostate cancer |
| US20040081659A1 (en) | 1997-12-02 | 2004-04-29 | Merck & Co., Inc. | Conjugates useful in the treatment of prostate cancer |
| AU2896399A (en) | 1998-03-03 | 1999-09-20 | Exact Sciences Corporation | Purification and detection processes using reversible affinity electrophoresis |
| US20020103136A1 (en) | 1998-03-05 | 2002-08-01 | Dong-Mei Feng | Conjugates useful in the treatment of prostate cancer |
| US6232287B1 (en) | 1998-03-13 | 2001-05-15 | The Burnham Institute | Molecules that home to various selected organs or tissues |
| AU757698C (en) | 1998-06-01 | 2004-04-08 | Agensys, Inc. | Novel serpentine transmembrane antigens expressed in human cancers and uses thereof |
| US6833438B1 (en) | 1999-06-01 | 2004-12-21 | Agensys, Inc. | Serpentine transmembrane antigens expressed in human cancers and uses thereof |
| US7138103B2 (en) | 1998-06-22 | 2006-11-21 | Immunomedics, Inc. | Use of bi-specific antibodies for pre-targeting diagnosis and therapy |
| US20070020327A1 (en) | 1998-11-10 | 2007-01-25 | John Fikes | Inducing cellular immune responses to prostate cancer antigens using peptide and nucleic acid compositions |
| US6174858B1 (en) | 1998-11-17 | 2001-01-16 | Merck & Co., Inc. | Conjugates useful in the treatment of prostate cancer |
| US20030207808A1 (en) | 1999-02-18 | 2003-11-06 | Kinneret Savitzky | Novel nucleic acid and amino acid sequences |
| WO2000059930A1 (en) | 1999-04-05 | 2000-10-12 | Merck & Co., Inc. | A method of treating cancer |
| US6528499B1 (en) | 2000-04-27 | 2003-03-04 | Georgetown University | Ligands for metabotropic glutamate receptors and inhibitors of NAALADase |
| CA2367787C (en) | 1999-04-28 | 2011-07-26 | Alan P. Kozikowski | Ligands for metabotropic glutamate receptors |
| AUPQ014799A0 (en) * | 1999-05-04 | 1999-05-27 | Access Pharmaceuticals Australia Pty Limited | Amplification of folate-mediated targeting to tumor cells using polymers |
| US7166573B1 (en) | 1999-05-28 | 2007-01-23 | Ludwig Institute For Cancer Research | Breast, gastric and prostate cancer associated antigens and uses therefor |
| US20040146516A1 (en) | 1999-06-17 | 2004-07-29 | Utah Ventures Ii L.P. | Lumen-exposed molecules and methods for targeted delivery |
| US7361338B2 (en) | 1999-10-05 | 2008-04-22 | Agensys, Inc. | Methods to inhibit growth of prostate cancer cells |
| US6692724B1 (en) * | 1999-10-25 | 2004-02-17 | Board Of Regents, The University Of Texas System | Ethylenedicysteine (EC)-drug conjugates, compositions and methods for tissue specific disease imaging |
| US6428785B1 (en) | 1999-10-28 | 2002-08-06 | Immunolytics Inc. | Method and composition for treating prostate cancer |
| CA2391534A1 (en) | 1999-11-15 | 2001-05-25 | Drug Innovation & Design, Inc. | Selective cellular targeting: multifunctional delivery vehicles |
| PL211872B1 (pl) | 2000-03-31 | 2012-07-31 | Purdue Research Foundation | Kompozycja farmaceutyczna |
| ES2518926T3 (es) * | 2000-06-02 | 2014-11-05 | Board Of Regents, The University Of Texas System | Conjugados de etilendicisteína y un análogo de glucosa |
| US20030072794A1 (en) | 2000-06-09 | 2003-04-17 | Teni Boulikas | Encapsulation of plasmid DNA (lipogenes™) and therapeutic agents with nuclear localization signal/fusogenic peptide conjugates into targeted liposome complexes |
| AU2002224401B2 (en) | 2000-10-16 | 2007-12-06 | Gilead Sciences, Inc. | Nucleic acid ligands to the prostate specific membrane antigen |
| US20020132983A1 (en) | 2000-11-30 | 2002-09-19 | Junghans Richard P. | Antibodies as chimeric effector cell receptors against tumor antigens |
| AU2002239403A1 (en) | 2000-12-01 | 2002-06-11 | The Johns Hopkins University | Tissue specific prodrugs |
| EP1390081A2 (en) | 2001-01-08 | 2004-02-25 | Neorx Corporation | Therapeutic and diagnostic compounds, compositions, and methods |
| WO2002098885A1 (en) | 2001-02-07 | 2002-12-12 | Beth Israel Deaconess Medical Center | Modified psma ligands and uses related thereto |
| WO2002074345A2 (en) | 2001-03-16 | 2002-09-26 | Johns Hopkins University School Of Medicine | Immune modulation by transduced hematopoietic stem cells expressing antigens and antigen-presenting cell regulatory molecules |
| EP1389209B1 (en) | 2001-04-24 | 2009-04-08 | Purdue Research Foundation | Folate mimetics and folate-receptor binding conjugates thereof |
| CA2445826C (en) | 2001-05-02 | 2014-03-25 | Purdue Research Foundation | Treatment and diagnosis of macrophage mediated disease |
| US20040092890A1 (en) | 2001-05-10 | 2004-05-13 | Ash Stephen R. | Catheter lock solution including a photo-oxidant |
| US7109165B2 (en) | 2001-05-18 | 2006-09-19 | Sirna Therapeutics, Inc. | Conjugates and compositions for cellular delivery |
| US7514078B2 (en) | 2001-06-01 | 2009-04-07 | Cornell Research Foundation, Inc. | Methods of treating prostate cancer with anti-prostate specific membrane antigen antibodies |
| EP2277542B1 (en) | 2001-06-01 | 2014-04-16 | Cornell Research Foundation Inc. | Modified antibodies to prostrate-specific membrane antigen and uses thereof |
| US20040018203A1 (en) | 2001-06-08 | 2004-01-29 | Ira Pastan | Pegylation of linkers improves antitumor activity and reduces toxicity of immunoconjugates |
| DE60232244D1 (de) | 2001-06-21 | 2009-06-18 | Glycomimetics Inc | Nachweis und behandlung von prostatakrebs |
| US20030031677A1 (en) | 2001-06-25 | 2003-02-13 | Drug Innovation & Design, Incorporated | Exponential pattern recognition based cellular targeting, compositions, methods and anticancer applications |
| US7893223B2 (en) | 2001-07-17 | 2011-02-22 | Bracco Imaging S.P.A. | Multidentate AZA ligands able to complex metal ions and the use thereof in diagnostics and therapy |
| PT1567641E (pt) | 2001-08-24 | 2012-08-21 | Uvic Industry Partnerships Inc | Proaerolisina contendo sequência de activação de proteases e métodos de uso para o tratamento do cancro da próstata |
| IL159422A0 (en) | 2001-09-20 | 2004-06-01 | Cornell Res Foundation Inc | Methods and compositions for treating or preventing skin disorders using binding agents specific for prostate-specific membrane antigen |
| US20030232760A1 (en) | 2001-09-21 | 2003-12-18 | Merck & Co., Inc. | Conjugates useful in the treatment of prostate cancer |
| KR20040053136A (ko) | 2001-09-28 | 2004-06-23 | 펄듀 리서치 파운데이션 | 리간드-면역원 공액체를 이용한 치료 방법 |
| US20030215456A1 (en) | 2001-10-02 | 2003-11-20 | Sui-Long Yao | Method of treating cancer |
| US20030133927A1 (en) | 2001-10-10 | 2003-07-17 | Defeo-Jones Deborah | Conjugates useful in the treatment of prostate cancer |
| US20040058857A1 (en) | 2001-11-29 | 2004-03-25 | Siu-Long Yao | Method of treating cancer |
| US20070031438A1 (en) | 2001-12-10 | 2007-02-08 | Junghans Richard P | Antibodies as chimeric effector cell receptors against tumor antigens |
| AU2003205077A1 (en) | 2002-01-10 | 2003-07-30 | Johns Hopkins University | Imaging agents and methods of imaging naaladase of psma |
| US7344700B2 (en) | 2002-02-28 | 2008-03-18 | University Of Tennessee Research Corporation | Radiolabeled selective androgen receptor modulators and their use in prostate cancer imaging and therapy |
| EP1497462A4 (en) | 2002-03-07 | 2007-11-07 | Univ Johns Hopkins Med | GENOMIC SCREEN ON EPIGENETIC MUTED CANCER ASSOCIATED GENES |
| US7534580B2 (en) | 2002-05-01 | 2009-05-19 | Ambrilia Biopharma Inc. | PSP94 diagnostic reagents and assays |
| DK2260875T3 (da) | 2002-05-06 | 2014-06-30 | Endocyte Inc | Folatreceptor-targetede billeddannelsesmidler |
| WO2003097647A1 (en) | 2002-05-15 | 2003-11-27 | Endocyte, Inc. | Vitamin-mitomycin conjugates |
| US7597876B2 (en) * | 2007-01-11 | 2009-10-06 | Immunomedics, Inc. | Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules |
| US7767803B2 (en) | 2002-06-18 | 2010-08-03 | Archemix Corp. | Stabilized aptamers to PSMA and their use as prostate cancer therapeutics |
| SI1545613T1 (sl) | 2002-07-31 | 2011-11-30 | Seattle Genetics Inc | Avristatinski konjugati in njihova uporaba za zdravljenje raka avtoimunske bolezni ali infekcijskebolezni |
| AR040956A1 (es) | 2002-07-31 | 2005-04-27 | Schering Ag | Nuevos conjugados de efectores, procedimientos para su preparacion y su uso farmaceutico |
| WO2006028429A2 (en) | 2002-08-05 | 2006-03-16 | The Johns Hopkins University | Peptides for targeting the prostate specific membrane antigen |
| AU2003259761A1 (en) | 2002-08-08 | 2004-02-25 | Johns Hopkins University | Enhancement of adenoviral oncolytic activity in prostate cells by modification of the e1a gene product |
| US8487128B2 (en) | 2002-11-26 | 2013-07-16 | Chs Pharma, Inc. | Protection of normal cells |
| US7875586B2 (en) | 2002-12-20 | 2011-01-25 | The Johns Hopkins University | Treatment of metastatic colon cancer with b-subunit of shiga toxin |
| US7226577B2 (en) | 2003-01-13 | 2007-06-05 | Bracco Imaging, S. P. A. | Gastrin releasing peptide compounds |
| US20080008649A1 (en) | 2003-01-13 | 2008-01-10 | Bracco Imaging S.P.A. | Gastrin Releasing Peptide Compounds |
| CN100381177C (zh) * | 2003-01-27 | 2008-04-16 | 恩多塞特公司 | 维生素受体结合递药缀合物 |
| DK1592457T3 (da) | 2003-01-27 | 2012-10-22 | Endocyte Inc | Folat-vinblastin-konjugat som lægemiddel |
| EP1587837B1 (en) | 2003-01-28 | 2012-06-13 | Proscan RX Pharma Inc. | Epitope sequences for prostate cancer diagnosis and treatment |
| EP1444990A1 (en) | 2003-02-07 | 2004-08-11 | Amersham plc | Improved Radiometal Complex Compositions |
| US7638122B2 (en) | 2003-03-07 | 2009-12-29 | University Of South Florida | Stat3 antagonists and their use as vaccines against cancer |
| WO2004080412A2 (en) | 2003-03-07 | 2004-09-23 | The University Of Toledo | Paclitaxel hybrid derivatives |
| US20070179100A1 (en) | 2003-04-09 | 2007-08-02 | Muthiah Manoharan | Protected monomers |
| DK1620544T3 (en) | 2003-04-17 | 2019-01-14 | Alnylam Pharmaceuticals Inc | MODIFIED iRNA AGENTS |
| EP1641742A4 (en) | 2003-05-01 | 2006-11-29 | Nst Neurosurvival Technologies | COMPOUNDS BINDING SELECTIVELY TO MEMBRANES OF APOPTOTIC CELLS |
| US8088387B2 (en) | 2003-10-10 | 2012-01-03 | Immunogen Inc. | Method of targeting specific cell populations using cell-binding agent maytansinoid conjugates linked via a non-cleavable linker, said conjugates, and methods of making said conjugates |
| CA2529027C (en) | 2003-06-13 | 2013-09-10 | Immunomedics, Inc. | D-amino acid peptides |
| US7232805B2 (en) | 2003-09-10 | 2007-06-19 | Inflabloc Pharmaceuticals, Inc. | Cobalamin conjugates for anti-tumor therapy |
| US20050085417A1 (en) * | 2003-10-16 | 2005-04-21 | Thomas Jefferson University | Compounds and methods for diagnostic imaging and therapy |
| US20050255042A1 (en) | 2003-11-24 | 2005-11-17 | The Regents Of The University Of California Office Of Technology Transfer, University Of California | On-demand cleavable linkers for radioconjugates for cancer imaging and therapy |
| FR2864546A1 (fr) | 2003-12-24 | 2005-07-01 | Assist Publ Hopitaux De Paris | Methode d'identification et de preparation de lymphocytes t regulateurs/suppresseurs, compositions et utilisations |
| US8586932B2 (en) | 2004-11-09 | 2013-11-19 | Spectrum Dynamics Llc | System and method for radioactive emission measurement |
| DE102004004787A1 (de) | 2004-01-30 | 2005-08-18 | Schering Ag | Neue Effektor-Konjugate, Verfahren zu ihrer Herstellung und ihre pharmazeutische Verwendung |
| EP1718667B1 (en) | 2004-02-23 | 2013-01-09 | Genentech, Inc. | Heterocyclic self-immolative linkers and conjugates |
| EP1610818A4 (en) | 2004-03-03 | 2007-09-19 | Millennium Pharm Inc | MODIFIED ANTIBODIES AGAINST A PROSTATE-SPECIFIC MEMBRANE-ANTIGEN AND USE THEREOF |
| EP1723430A2 (fr) | 2004-03-03 | 2006-11-22 | Biomerieux | Procede de detection de la forme libre activable du psa et son utilisation pour le diagnostic des pathologies benignes de la prostate et de l adenocarcinome de la prostate |
| ES2311895T3 (es) | 2004-03-15 | 2009-02-16 | F. Hoffmann-La Roche Ag | El uso de los peptidos tipo bnp y de los peptidos tipo anf para evaluar el riesgo de padecer una complicacion cardio-vascular como frecuencia de sobrecarga del volumen. |
| US20060105975A1 (en) | 2004-04-19 | 2006-05-18 | Shannon Pendergrast | Aptamer-mediated intracellular delivery of therapeutic oligonucleotides |
| EP1756166A4 (en) | 2004-04-19 | 2008-08-27 | Proscan Rx Pharma | DIAGNOSIS AND TREATMENT OF PROSTATE CANCER |
| RU2402548C2 (ru) | 2004-05-19 | 2010-10-27 | Медарекс, Инк. | Химические линкеры и их конъюгаты |
| JP4806680B2 (ja) | 2004-05-19 | 2011-11-02 | メダレックス インコーポレイテッド | 自己犠牲リンカー及び薬剤複合体 |
| US20080008719A1 (en) | 2004-07-10 | 2008-01-10 | Bowdish Katherine S | Methods and compositions for the treatment of prostate cancer |
| JP5149620B2 (ja) | 2004-07-23 | 2013-02-20 | エンドサイト，インコーポレイテッド | ２価リンカーおよびその結合体 |
| PL1776384T3 (pl) | 2004-08-04 | 2013-10-31 | Mentrik Biotech Llc | WARIANTY REGIONÓW Fc |
| MX2007002410A (es) | 2004-08-30 | 2007-05-07 | Neuromed Pharmaceuticals Ltd | Derivados de urea como bloqueadores de canal de calcio. |
| US7713944B2 (en) | 2004-10-13 | 2010-05-11 | Isis Pharmaceuticals, Inc. | Oligomers comprising activated disulfides which bind to plasma proteins and their use for delivery to cells |
| WO2006049891A1 (en) | 2004-10-27 | 2006-05-11 | Janssen Pharmaceutica N.V. | Trisubstituted thiophenes as progesterone receptor modulators |
| EP1827505A4 (en) | 2004-11-09 | 2017-07-12 | Biosensors International Group, Ltd. | Radioimaging |
| US8423125B2 (en) | 2004-11-09 | 2013-04-16 | Spectrum Dynamics Llc | Radioimaging |
| US20060140871A1 (en) | 2004-11-30 | 2006-06-29 | Sillerud Laurel O | Magnetic resonance imaging of prostate cancer |
| US7872235B2 (en) | 2005-01-13 | 2011-01-18 | Spectrum Dynamics Llc | Multi-dimensional image reconstruction and analysis for expert-system diagnosis |
| US20060155021A1 (en) | 2005-01-13 | 2006-07-13 | Lenges Christian P | Coating compositions containing rheology control agents |
| US7741510B2 (en) | 2005-01-13 | 2010-06-22 | E. I. Du Pont De Nemours And Company | Rheology control agents |
| US20090258002A1 (en) | 2005-02-01 | 2009-10-15 | Government Of The Us, As Represented By The Secretary, Department Of Health And Human Services | Biomarkers for Tissue Status |
| WO2006093991A1 (en) | 2005-03-02 | 2006-09-08 | The Cleveland Clinic Foundation | Compounds which bind psma and uses thereof |
| WO2006096754A2 (en) | 2005-03-07 | 2006-09-14 | Archemix Corp. | Stabilized aptamers to psma and their use as prostate cancer therapeutics |
| WO2006104911A2 (en) | 2005-03-25 | 2006-10-05 | Genentech, Inc. | Methods and compositions for modulating hyperstabilized c-met |
| US8088908B2 (en) | 2005-05-10 | 2012-01-03 | City Of Hope | Humanized anti-prostate stem cell antigen monoclonal antibody |
| KR101068612B1 (ko) | 2005-05-24 | 2011-09-30 | 휴마시스 주식회사 | 유사구조 단백질 비율 측정을 이용한 진단장치 |
| EP1891093B1 (en) | 2005-06-14 | 2011-03-23 | Protox Therapeutics Incorporated | Method of treating or preventing benign prostatic hyperplasia using modified pore-forming proteins |
| NZ565075A (en) | 2005-06-20 | 2011-05-27 | Psma Dev Company Llc | PSMA antibody-drug conjugates |
| US20070010014A1 (en) | 2005-07-06 | 2007-01-11 | General Electric Company | Compositions and methods for enhanced delivery to target sites |
| EP1909853B1 (en) | 2005-07-19 | 2015-03-18 | Biosensors International Group, Ltd. | Imaging protocols |
| AU2006279304A1 (en) | 2005-08-19 | 2007-02-22 | Endocyte, Inc. | Multi-drug ligand conjugates |
| EP2382995A3 (en) | 2005-08-19 | 2013-09-25 | Endocyte, Inc. | Ligand conjugates of Vinca alkaloids, analogs and derivatives |
| US20100144641A1 (en) | 2005-09-12 | 2010-06-10 | Popel Aleksander S | Compositions Having Antiangiogenic Activity and Uses Thereof |
| EP1940841B9 (fr) * | 2005-10-07 | 2017-04-19 | Guerbet | Composes comprenant une partie de reconnaissance d'une cible biologique, couplee a une partie de signal capable de complexer le gallium |
| WO2008048298A2 (en) | 2005-11-21 | 2008-04-24 | Medivas, Llc | Polymer particles for delivery of macromolecules and methods of use |
| DK2963011T3 (en) | 2005-11-23 | 2018-08-06 | Ventana Med Syst Inc | MOLECULAR CONJUGATE |
| WO2007081751A2 (en) | 2006-01-05 | 2007-07-19 | The Johns Hopkins University | Compositions and methods for the treatment of cancer |
| US7635682B2 (en) | 2006-01-06 | 2009-12-22 | Genspera, Inc. | Tumor activated prodrugs |
| JP2009532338A (ja) | 2006-03-14 | 2009-09-10 | キャンサー ターゲテッド テクノロジー エルエルシー | Ｐｓｍａのペプチド模倣体阻害剤、それらを含む化合物、およびそれらの使用方法 |
| WO2007109321A2 (en) | 2006-03-20 | 2007-09-27 | The Regents Of The University Of California | Engineered anti-prostate stem cell antigen (psca) antibodies for cancer targeting |
| US20070225213A1 (en) | 2006-03-23 | 2007-09-27 | Kosak Matthew K | Nucleic acid carriers for delivery of therapeutic agents |
| US20140314864A1 (en) | 2006-03-31 | 2014-10-23 | Massachusetts Institute Of Technology | System for Targeted Delivery of Therapeutic Agents |
| ES2776100T3 (es) | 2006-03-31 | 2020-07-29 | Massachusetts Inst Technology | Sistema para el suministro dirigido de agentes terapéuticos |
| US9265746B2 (en) * | 2006-05-31 | 2016-02-23 | Merck & Cie | Method for cell-specific targeting |
| US7842280B2 (en) | 2006-09-06 | 2010-11-30 | Case Western Reserve University | Flexibly labeling peptides |
| US10925977B2 (en) * | 2006-10-05 | 2021-02-23 | Ceil>Point, LLC | Efficient synthesis of chelators for nuclear imaging and radiotherapy: compositions and applications |
| JP2010509570A (ja) | 2006-11-03 | 2010-03-25 | パーデュー・リサーチ・ファウンデーション | エクスビボフローサイトメトリーの方法および装置 |
| ES2847275T3 (es) | 2006-11-08 | 2021-08-02 | Molecular Insight Pharm Inc | Heterodímeros de ácido glutámico |
| US8956602B2 (en) | 2006-12-05 | 2015-02-17 | Landec, Inc. | Delivery of drugs |
| WO2008085828A2 (en) | 2007-01-03 | 2008-07-17 | The Johns Hopkins University | Peptide modulators of angiogenesis and use thereof |
| US20160045626A1 (en) * | 2007-01-11 | 2016-02-18 | Immunomedics, Inc. | Methods and Compositions for Improved Labeling of Targeting Peptides |
| US8709382B2 (en) * | 2007-01-11 | 2014-04-29 | Immunomedics, Inc. | Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules |
| US8889100B2 (en) * | 2007-01-11 | 2014-11-18 | Immunomedics, Inc. | Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules |
| AU2007343600B2 (en) * | 2007-01-11 | 2012-06-28 | Immunomedics, Inc. | Methods and compositions for improved F-18 labeling of proteins, peptides and other molecules |
| US20080214436A1 (en) | 2007-01-26 | 2008-09-04 | City Of Hope | Methods and compositions for the treatment of cancer or other diseases |
| US8586595B2 (en) | 2007-02-07 | 2013-11-19 | Purdue Research Foundation | Positron emission tomography imaging method |
| WO2008101231A2 (en) * | 2007-02-16 | 2008-08-21 | Endocyte, Inc. | Methods and compositions for treating and diagnosing kidney disease |
| CN104127878A (zh) | 2007-03-14 | 2014-11-05 | 恩多塞特公司 | 结合配体连接的微管溶素递药缀合物 |
| EP2136788B1 (en) | 2007-03-30 | 2011-10-26 | Bind Biosciences, Inc. | Cancer cell targeting using nanoparticles |
| WO2008124197A1 (en) | 2007-04-10 | 2008-10-16 | The Johns Hopkins University | Imaging and therapy of virus-associated tumors |
| BRPI0812970A2 (pt) | 2007-06-25 | 2019-09-24 | Endocyte Inc | conjugados contendo espaçadores hidrofílicos |
| CA2926573C (en) | 2007-06-26 | 2018-08-28 | The Johns Hopkins University | Labeled inhibitors of prostate specific membrane antigen (psma), biological evaluation, and use as imaging agents |
| GB0723246D0 (en) | 2007-07-03 | 2008-01-09 | Barton Michelle | p53 modulator |
| EP2170946A2 (en) | 2007-07-13 | 2010-04-07 | The Johns Hopkins University | B7-dc variants |
| RU2010107199A (ru) | 2007-07-31 | 2011-09-10 | Дзе Джонс Хопкинс Юниверсити (Us) | Конъюгат полипептид-нуклеиновая кислота для иммунопрофилактики или иммунотерапии для неопластических или инфекционных нарушений |
| EP4464384A3 (en) | 2007-08-17 | 2025-01-08 | Purdue Research Foundation | Psma binding ligand-linker conjugates and methods for using |
| EP2185188B1 (en) | 2007-08-22 | 2014-08-06 | Medarex, L.L.C. | Site-specific attachment of drugs or other agents to engineered antibodies with c-terminal extensions |
| WO2009035942A1 (en) | 2007-09-13 | 2009-03-19 | Chemimage Corporation | Distinguishing between renal oncocytoma and chromophobe renal cell carcinoma using raman molecular imaging |
| US9187521B2 (en) | 2007-10-25 | 2015-11-17 | Endocyte, Inc. | Tubulysins and processes for preparing |
| US8450290B2 (en) | 2007-11-26 | 2013-05-28 | Enzon Pharmaceuticals, Inc. | Methods for treating androgen receptor dependent disorders including cancers |
| WO2009070302A1 (en) | 2007-11-30 | 2009-06-04 | The Johns Hopkins University | Prostate specific membrane antigen (psma) targeted nanoparticles for therapy of prostate cancer |
| EP2231194B1 (en) | 2007-12-04 | 2017-02-22 | Alnylam Pharmaceuticals Inc. | Folate-irna conjugates |
| WO2009076434A1 (en) | 2007-12-12 | 2009-06-18 | Molecular Insight Pharmaceuticals, Inc. | Inhibitors of integrin vla-4 |
| CA2711678A1 (en) | 2008-01-09 | 2009-07-16 | Molecular Insight Pharmaceuticals, Inc. | Inhibitors of carbonic anhydrase ix |
| ITTO20080313A1 (it) | 2008-04-22 | 2009-10-23 | Marco Colombatti | Anticorpo monoclonale isolato o suo frammento legante l'antigene specifico di membrana della prostata, suoi coniugati e suoi usi |
| US8258111B2 (en) | 2008-05-08 | 2012-09-04 | The Johns Hopkins University | Compositions and methods related to miRNA modulation of neovascularization or angiogenesis |
| SI2291659T1 (sl) | 2008-05-13 | 2016-02-29 | Yale University | Himerične majhne molekule za pridobivanje protiteles za rakave celice |
| US8852630B2 (en) | 2008-05-13 | 2014-10-07 | Yale University | Chimeric small molecules for the recruitment of antibodies to cancer cells |
| JP2012501965A (ja) | 2008-06-16 | 2012-01-26 | バインド バイオサイエンシズ インコーポレイテッド | 薬剤を装填したポリマーナノ粒子及びその製造方法と使用方法 |
| RU2494096C2 (ru) | 2008-08-01 | 2013-09-27 | Дзе Джонс Хопкинс Юниверсити | Агенты, связывающиеся с psma, и их применение |
| EP2320913A4 (en) * | 2008-08-09 | 2012-10-03 | Univ Iowa Res Found | NUKLEINSÄUREAPTAMERE |
| CA2734322A1 (en) | 2008-08-15 | 2010-02-18 | Georgetown University | Na channels, disease, and related assays and compositions |
| EP2326350B1 (en) | 2008-09-08 | 2013-09-04 | Psma Development Company, L.L.C. | Compounds for killing psma-expressing, taxane-resistant cancer cells |
| EP2166021A1 (en) | 2008-09-16 | 2010-03-24 | Ganymed Pharmaceuticals AG | Monoclonal antibodies for treatment of cancer |
| AU2009293140A1 (en) | 2008-09-17 | 2010-03-25 | Endocyte, Inc. | Folate receptor binding conjugates of antifolates |
| WO2010045598A2 (en) | 2008-10-17 | 2010-04-22 | Purdue Research Foundation | Psma binding ligand-linker conjugates and methods for using |
| WO2010065906A2 (en) | 2008-12-05 | 2010-06-10 | Molecular Insight Pharmaceuticals, Inc. | Ca-ix specific radiopharmaceuticals for the treatment and imaging of cancer |
| TW201034691A (en) | 2008-12-05 | 2010-10-01 | Molecular Insight Pharm Inc | Technetium-and rhenium-bis(heteroaryl) complexes and methods of use thereof |
| WO2010065899A2 (en) | 2008-12-05 | 2010-06-10 | Molecular Insight Pharmaceuticals, Inc. | Technetium-and rhenium-bis(heteroaryl)complexes and methods of use thereof |
| EP2398504B1 (en) | 2009-02-17 | 2018-11-28 | Cornell Research Foundation, Inc. | Methods and kits for diagnosis of cancer and prediction of therapeutic value |
| US8772226B2 (en) | 2009-03-17 | 2014-07-08 | The Johns Hopkins University | Methods and compositions for the detection of cancer |
| AU2010249719A1 (en) | 2009-05-19 | 2012-05-31 | Aic Blab Company | Composite current collector and methods therefor |
| AU2010260195B2 (en) | 2009-06-15 | 2014-11-20 | Molecular Insight Pharmaceuticals, Inc. | Process for production of heterodimers of glutamic acid |
| EP2460013A4 (en) | 2009-07-31 | 2013-04-03 | Endocyte Inc | ON FOLLOWING DIAGNOSIS AND TREATMENT |
| US8394922B2 (en) | 2009-08-03 | 2013-03-12 | Medarex, Inc. | Antiproliferative compounds, conjugates thereof, methods therefor, and uses thereof |
| US8313128B2 (en) | 2009-08-20 | 2012-11-20 | Rhoost, Llc. | Safety locking mechanism for doors |
| WO2011031517A1 (en) | 2009-08-27 | 2011-03-17 | Nuclea Biotechnologies, LLC | Method and assay for determining fas expression |
| CA2782333C (en) | 2009-12-02 | 2019-06-04 | Imaginab, Inc. | J591 minibodies and cys-diabodies for targeting human prostate specific membrane antigen (psma) and methods for their use |
| US8357401B2 (en) | 2009-12-11 | 2013-01-22 | Bind Biosciences, Inc. | Stable formulations for lyophilizing therapeutic particles |
| MX338831B (es) | 2010-02-04 | 2016-05-03 | Radius Health Inc | Moduladores selectivos de receptores de androgenos. |
| US9951324B2 (en) | 2010-02-25 | 2018-04-24 | Purdue Research Foundation | PSMA binding ligand-linker conjugates and methods for using |
| JP2010159277A (ja) | 2010-03-04 | 2010-07-22 | Sumitomo Chemical Co Ltd | 有害生物防除組成物及び有害生物の防除方法 |
| DK2528625T3 (da) | 2010-04-15 | 2013-10-14 | Spirogen Sarl | Pyrrolobenzodiazepiner og konjugater deraf |
| CN101863924B (zh) * | 2010-05-17 | 2012-06-27 | 北京师范大学 | 99mTc标记肼基烟酰胺基-二氧辛酰-叶酸配合物及制备方法 |
| KR101236142B1 (ko) | 2010-09-30 | 2013-02-21 | 경북대학교 산학협력단 | 가돌리늄 착물을 함유하는 ｍｒｉ조영제 |
| US9687572B2 (en) | 2010-12-06 | 2017-06-27 | Molecular Insight Pharmaceuticals, Inc. | PSMA-targeted dendrimers |
| WO2012166923A2 (en) | 2011-05-31 | 2012-12-06 | Bind Biosciences | Drug loaded polymeric nanoparticles and methods of making and using same |
| WO2012174136A1 (en) | 2011-06-15 | 2012-12-20 | Cancer Targeted Technology Llc | Chelated psma inhibitors |
| WO2013022797A1 (en) | 2011-08-05 | 2013-02-14 | Molecular Insight Pharmaceuticals | Radiolabeled prostate specific membrane antigen inhibitors |
| WO2013028664A1 (en) * | 2011-08-22 | 2013-02-28 | Siemens Medical Solutions Usa, Inc. | Psma imaging agents |
| EP2822386B1 (en) * | 2012-02-29 | 2021-05-05 | Purdue Research Foundation | Folate receptor alpha binding ligands |
| EP2908818A4 (en) * | 2012-10-16 | 2016-07-13 | Endocyte Inc | CONJUGATES OF DRUG DELIVERY CONTAINING ARTIFICIAL AMINO ACIDS AND METHODS OF USE |
| US20140107316A1 (en) | 2012-10-16 | 2014-04-17 | Endocyte, Inc. | Drug delivery conjugates containing unnatural amino acids and methods for using |
| BR112015011118B1 (pt) * | 2012-11-15 | 2022-12-13 | Endocyte, Inc | Conjugado; composição farmacêutica; e uso de um conjugado |
| US20140154702A1 (en) | 2012-11-30 | 2014-06-05 | Endocyte, Inc. | Methods For Treating Cancer Using Combination Therapies |
| CN105246894A (zh) | 2012-12-21 | 2016-01-13 | 斯皮罗根有限公司 | 用于治疗增殖性和自身免疫疾病的非对称吡咯并苯并二氮杂卓二聚物 |
| US20140187501A1 (en) | 2012-12-28 | 2014-07-03 | Blend Therapeutics, Inc. | Targeted Conjugates Encapsulated in Particles and Formulations Thereof |
| EP2958596B1 (en) | 2013-02-15 | 2019-12-04 | Case Western Reserve University | Psma ligands and uses thereof |
| US20140249315A1 (en) | 2013-03-01 | 2014-09-04 | Endocyte, Inc. | Processes for preparing tubulysins |
| CA2921507A1 (en) * | 2013-08-22 | 2015-02-26 | Robert Doyle | Compositions comprising vitamin b12 and intrinsic factor and methods of use thereof |
| US10406246B2 (en) | 2013-10-17 | 2019-09-10 | Deutsches Kresbsforschungszentrum | Double-labeled probe for molecular imaging and use thereof |
| LT4095130T (lt) | 2013-10-18 | 2024-04-25 | Novartis Ag | Žymėti prostatos specifinio membranos antigeno (psma) inhibitoriai, jų naudojimas kaip vizualizavimo medžiagų ir farmacinių medžiagų prostatos vėžiui gydyti |
| US20150110814A1 (en) | 2013-10-18 | 2015-04-23 | Psma Development Company, Llc | Combination therapies with psma ligand conjugates |
| BR112016010927A2 (pt) | 2013-11-14 | 2017-08-08 | Endocyte Inc | Conjugado de fórmula |
| CN105828863B (zh) | 2013-12-18 | 2020-06-09 | 皇家飞利浦有限公司 | 基于心脏或呼吸特性来增强睡眠慢波活动的系统和方法 |
| CN103951668A (zh) * | 2014-04-25 | 2014-07-30 | 广州军区广州总医院 | 叶酸衍生物的正电子核素标记物及其应用 |
| AU2015256002B2 (en) | 2014-05-06 | 2020-01-02 | Northwestern University | Metal/radiometal-labeled PSMA inhibitors for PSMA-targeted imaging and radiotherapy |
| US9988407B2 (en) | 2014-08-06 | 2018-06-05 | The Johns Hopkins University | Prodrugs of prostate specific membrane antigen (PSMA) inhibitor |
| EP3183236B1 (en) | 2014-08-24 | 2022-04-20 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften | Method for the production of 18f-labeled active esters and their application exemplified by the preparation of a psma-specific pet-tracer |
| EP2993171A1 (en) | 2014-09-04 | 2016-03-09 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Method for the production of 18F-labeled PSMA-specific PET-tracers |
| AU2015315465B2 (en) | 2014-09-08 | 2019-08-29 | Molecular Insight Pharmaceuticals, Inc. | Organ protection in PSMA-targeted radionuclide therapy of prostate cancer |
| US10188759B2 (en) | 2015-01-07 | 2019-01-29 | Endocyte, Inc. | Conjugates for imaging |
| CA2968141C (en) | 2015-01-16 | 2020-08-04 | Hsing-Mao CHU | Molecular constructs with targeting and effector elements |
| IL237525A (en) | 2015-03-03 | 2017-05-29 | Shalom Eli | Method for labeling a prostate-specific membrane antigen with a radioactive isotope |
| US9808538B2 (en) | 2015-09-09 | 2017-11-07 | On Target Laboratories, LLC | PSMA-targeted NIR dyes and their uses |
| KR101639599B1 (ko) | 2015-11-09 | 2016-07-14 | 서울대학교산학협력단 | 펩타이드 싸이오우레아 유도체, 이를 포함하는 방사성 동위원소 표지 화합물 및 이를 유효 성분으로 함유하는 전립선암 치료 또는 진단용 약학적 조성물 |
| FR3043970B1 (fr) | 2015-11-25 | 2019-06-21 | Medtech Sa | Systeme mecanique de stabilisation au sol pour vehicules a roulettes |
| US10688200B2 (en) | 2015-12-31 | 2020-06-23 | Five Eleven Pharma Inc. | Urea-based prostate specific membrane antigen (PSMA) inhibitors for imaging and therapy |
| EP3496707A4 (en) | 2016-08-09 | 2020-03-25 | Angimmune, LLC | Treatment of cancer using a combination of immunomodulation and check point inhibitors |
| EP3510399B1 (en) | 2016-09-09 | 2023-03-01 | On Target Laboratories, LLC | Psma-targeted nir dyes and their uses |
| WO2018108287A1 (en) | 2016-12-15 | 2018-06-21 | The European Atomic Energy Community (Euratom), Represented By The European Commission | Treatment of pmsa expressing cancers |
| EP3607319A1 (en) | 2017-04-07 | 2020-02-12 | Juno Therapeutics, Inc. | Engineered cells expressing prostate-specific membrane antigen (psma) or a modified form thereof and related methods |
| SG11201909513QA (en) | 2017-04-11 | 2019-11-28 | Univ Johns Hopkins | Prodrugs of 2-pmpa for healthy tissue protection during psma-targeted cancer imaging or radiotherapy |
| SG11202005511VA (en) | 2017-12-13 | 2020-07-29 | Sciencons AS | Complex comprising a psma-targeting compound linked to a lead or thorium radionuclide |
| AU2019225154B2 (en) | 2018-02-22 | 2024-10-24 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Chemical conjugates of evans blue derivatives and their use as radiotherapy and imaging agents for targeting prostate cancer |
| US12208102B2 (en) | 2018-04-17 | 2025-01-28 | Endocyte, Inc. | Methods of treating cancer |
| WO2019246514A1 (en) | 2018-06-21 | 2019-12-26 | Regeneron Pharmaceuticals, Inc. | Bispecific anti-psma x anti-cd28 antibodies and uses thereof |
| CN109134602B (zh) | 2018-08-28 | 2021-07-02 | 兰州大学 | 一种高效的前列腺特异性膜抗原配体psma-617的固相制备方法 |
| EP3853213A4 (en) | 2018-09-21 | 2022-07-06 | Endocyte, Inc. | Shielding agents and their use |
| CA3112806A1 (en) | 2018-09-21 | 2020-03-26 | Endocyte, Inc. | Methods of treating cancer |
| CN114096264B (zh) | 2019-05-20 | 2025-03-14 | 因多塞特股份有限公司 | 制备psma缀合物的方法 |
| EP4107279A4 (en) | 2020-02-18 | 2024-07-17 | Endocyte, Inc. | METHOD FOR TREATING CANCERS EXPRESSING PSMA |
-
2014
- 2014-11-13 BR BR112016010927A patent/BR112016010927A2/pt active Search and Examination
- 2014-11-13 EP EP14861854.9A patent/EP3069147A4/en not_active Withdrawn
- 2014-11-13 MX MX2016006219A patent/MX2016006219A/es unknown
- 2014-11-13 EP EP19167560.2A patent/EP3533473A3/en not_active Withdrawn
- 2014-11-13 EP EP20180928.2A patent/EP3777898B1/en active Active
- 2014-11-13 AU AU2014348601A patent/AU2014348601A1/en not_active Abandoned
- 2014-11-13 JP JP2016529948A patent/JP6464166B2/ja active Active
- 2014-11-13 US US15/035,936 patent/US20160287731A1/en not_active Abandoned
- 2014-11-13 SG SG10201803618RA patent/SG10201803618RA/en unknown
- 2014-11-13 CA CA2930581A patent/CA2930581A1/en active Pending
- 2014-11-13 CN CN201480071256.XA patent/CN105849568B/zh active Active
- 2014-11-13 EP EP24221005.2A patent/EP4541378A3/en active Pending
- 2014-11-13 CN CN201810300332.XA patent/CN108514646B/zh active Active
- 2014-11-13 KR KR1020167015740A patent/KR102457827B1/ko active Active
- 2014-11-13 ES ES20180928T patent/ES3013992T3/es active Active
- 2014-11-13 EA EA201690862A patent/EA035171B1/ru unknown
- 2014-11-13 WO PCT/US2014/065467 patent/WO2015073678A1/en not_active Ceased
- 2014-11-14 TW TW103139664A patent/TWI657827B/zh active
-
2016
- 2016-05-11 IL IL245612A patent/IL245612A0/en active IP Right Grant
- 2016-05-12 MX MX2022014611A patent/MX2022014611A/es unknown
-
2018
- 2018-08-20 IL IL261259A patent/IL261259B/en active IP Right Grant
- 2018-10-10 US US16/157,024 patent/US20190275181A1/en not_active Abandoned
- 2018-11-06 JP JP2018208786A patent/JP2019023232A/ja active Pending
-
2020
- 2020-03-30 JP JP2020060644A patent/JP2020165975A/ja active Pending
-
2021
- 2021-01-07 AU AU2021200067A patent/AU2021200067B2/en active Active
- 2021-09-29 US US17/488,810 patent/US12178892B2/en active Active
- 2021-10-27 JP JP2021175168A patent/JP7299285B2/ja active Active
-
2023
- 2023-05-02 AU AU2023202704A patent/AU2023202704B2/en active Active
- 2023-06-15 JP JP2023098521A patent/JP7693751B2/ja active Active
-
2024
- 2024-10-11 US US18/913,734 patent/US20250127939A1/en active Pending
-
2025
- 2025-05-01 AU AU2025203132A patent/AU2025203132A1/en active Pending
- 2025-06-05 JP JP2025093836A patent/JP2025120291A/ja active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7399460B2 (en) * | 1998-05-16 | 2008-07-15 | Bracco International B.V. | Metal complexes derivatized with folate for use in diagnostic and therapeutic applications |
| US20090214636A1 (en) * | 2005-07-05 | 2009-08-27 | Low Philip S | Imaging and Therapeutic Method Using Monocytes |
| US20120009121A1 (en) * | 2009-03-19 | 2012-01-12 | The Johns Hopkins University | Psma-targeting compounds and uses thereof |
| US20120322741A1 (en) * | 2010-02-25 | 2012-12-20 | Purdue Research Foundation | Psma binding ligand-linker conjugates and methods for using |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EA035171B1 (ru) | Конъюгаты на основе связывающихся с psma лигандов или ингибиторов psma для позитронно-эмиссионной томографии | |
| ES2914593T3 (es) | Agentes de unión a PSMA y usos de los mismos | |
| EP3209336A1 (en) | 18f-tagged inhibitors of prostate specific membrane antigen (psma), their use as imaging agents and pharmaceutical agents for the treatment of prostate cancer | |
| EP3011976A1 (en) | 18F-tagged inhibitors of prostate specific membrane antigen (PSMA), their use as imaging agents | |
| KR20230155494A (ko) | 글루타메이트-우레아-라이신 유래(gul 유래) 전립선-특이적 막 항원(psma) 표적화 접합체의 고체상 합성 및 치료 및/또는 진단제의 전구체로서 이들의 용도 | |
| HK40046458B (en) | Compounds for positron emission tomography | |
| EA048385B1 (ru) | Соединения для позитронно-эмиссионной томографии | |
| HK1259758A1 (en) | Compounds for positron emission tomography | |
| HK40046458A (en) | Compounds for positron emission tomography | |
| JP2025526760A (ja) | 放射性医薬品 | |
| NZ719939B2 (en) | Compounds for positron emission tomography | |
| HK40029571B (zh) | 伊文思蓝衍生物的化学缀合物及其作为靶向前列腺癌的放射疗法和显像剂的用途 | |
| CA2996330A1 (en) | 18f-tagged inhibitors of prostate specific membrane antigen (psma) and their use as imaging agents for prostate cancer |