TWI244925B - New imaging agents, precursors thereof and methods of manufacture - Google Patents
New imaging agents, precursors thereof and methods of manufacture Download PDFInfo
- Publication number
- TWI244925B TWI244925B TW091111997A TW91111997A TWI244925B TW I244925 B TWI244925 B TW I244925B TW 091111997 A TW091111997 A TW 091111997A TW 91111997 A TW91111997 A TW 91111997A TW I244925 B TWI244925 B TW I244925B
- Authority
- TW
- Taiwan
- Prior art keywords
- compound
- scope
- item
- patent application
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 title abstract description 6
- 239000012216 imaging agent Substances 0.000 title description 7
- 239000002243 precursor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 86
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 11
- 239000000203 mixture Substances 0.000 claims abstract description 9
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- 206010028980 Neoplasm Diseases 0.000 claims description 31
- -1 sulfofluorenyl Chemical group 0.000 claims description 27
- 238000011049 filling Methods 0.000 claims description 21
- 201000011510 cancer Diseases 0.000 claims description 12
- 125000006239 protecting group Chemical group 0.000 claims description 10
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 8
- 230000002079 cooperative effect Effects 0.000 claims description 6
- 125000006242 amine protecting group Chemical group 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 210000004185 liver Anatomy 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical group C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 210000000481 breast Anatomy 0.000 claims description 2
- 125000003865 brosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)S(*)(=O)=O 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims 2
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 1
- 208000003174 Brain Neoplasms Diseases 0.000 claims 1
- 229910014033 C-OH Inorganic materials 0.000 claims 1
- 229910014570 C—OH Inorganic materials 0.000 claims 1
- 235000011511 Diospyros Nutrition 0.000 claims 1
- 244000236655 Diospyros kaki Species 0.000 claims 1
- 102100021022 Gastrin Human genes 0.000 claims 1
- 108010052343 Gastrins Proteins 0.000 claims 1
- 208000009956 adenocarcinoma Diseases 0.000 claims 1
- AOXOCDRNSPFDPE-UKEONUMOSA-N chembl413654 Chemical compound C([C@H](C(=O)NCC(=O)N[C@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC=CC=1)C(N)=O)NC(=O)[C@@H](C)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H]1N(CCC1)C(=O)CNC(=O)[C@@H](N)CCC(O)=O)C1=CC=C(O)C=C1 AOXOCDRNSPFDPE-UKEONUMOSA-N 0.000 claims 1
- 210000000720 eyelash Anatomy 0.000 claims 1
- 125000005597 hydrazone group Chemical group 0.000 claims 1
- 230000000968 intestinal effect Effects 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 208000026310 Breast neoplasm Diseases 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 229940024606 amino acid Drugs 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 210000003205 muscle Anatomy 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 210000004072 lung Anatomy 0.000 description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- 238000002603 single-photon emission computed tomography Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 4
- 206010006187 Breast cancer Diseases 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 238000003384 imaging method Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000002600 positron emission tomography Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000002285 radioactive effect Effects 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
- 229960004441 tyrosine Drugs 0.000 description 3
- RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- NHTGHBARYWONDQ-JTQLQIEISA-N L-α-methyl-Tyrosine Chemical compound OC(=O)[C@](N)(C)CC1=CC=C(O)C=C1 NHTGHBARYWONDQ-JTQLQIEISA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 206010000269 abscess Diseases 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 210000000988 bone and bone Anatomy 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 210000003734 kidney Anatomy 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 210000000952 spleen Anatomy 0.000 description 2
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 2
- XLYOFNOQVPJJNP-NJFSPNSNSA-N ((18)O)water Chemical compound [18OH2] XLYOFNOQVPJJNP-NJFSPNSNSA-N 0.000 description 1
- NHTGHBARYWONDQ-UHFFFAOYSA-N (+-)-α-methyl-tyrosine Chemical compound OC(=O)C(N)(C)CC1=CC=C(O)C=C1 NHTGHBARYWONDQ-UHFFFAOYSA-N 0.000 description 1
- NLPKNOWZXJIOAH-LBPRGKRZSA-N (2S)-2-(hydroxyamino)-3-(1H-indol-3-yl)-2-methylpropanoic acid Chemical compound C1=CC=C2C(C[C@](C)(NO)C(O)=O)=CNC2=C1 NLPKNOWZXJIOAH-LBPRGKRZSA-N 0.000 description 1
- CDUUKBXTEOFITR-BYPYZUCNSA-N 2-methyl-L-serine Chemical compound OC[C@@]([NH3+])(C)C([O-])=O CDUUKBXTEOFITR-BYPYZUCNSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 101100189168 Capsicum frutescens PAMT gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 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 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 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
- 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
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AXDLCFOOGCNDST-UHFFFAOYSA-N N-methyl-DL-tyrosine Natural products CNC(C(O)=O)CC1=CC=C(O)C=C1 AXDLCFOOGCNDST-UHFFFAOYSA-N 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 description 1
- 102000004142 Trypsin Human genes 0.000 description 1
- 108090000631 Trypsin Proteins 0.000 description 1
- KRHYYFGTRYWZRS-BJUDXGSMSA-N ac1l2y5h Chemical compound [18FH] KRHYYFGTRYWZRS-BJUDXGSMSA-N 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- CDUUKBXTEOFITR-UHFFFAOYSA-N alpha-methylserine Natural products OCC([NH3+])(C)C([O-])=O CDUUKBXTEOFITR-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- WOBLPDAWNVAVAS-UHFFFAOYSA-N butyl carboxy carbonate Chemical compound CCCCOC(=O)OC(O)=O WOBLPDAWNVAVAS-UHFFFAOYSA-N 0.000 description 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 238000006115 defluorination reaction Methods 0.000 description 1
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000011534 incubation Methods 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
- 230000016507 interphase Effects 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000002751 lymph Anatomy 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 201000001441 melanoma Diseases 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 229960005190 phenylalanine Drugs 0.000 description 1
- 239000002953 phosphate buffered saline Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- BHMBVRSPMRCCGG-OUTUXVNYSA-N prostaglandin D2 Chemical compound CCCCC[C@H](O)\C=C\[C@@H]1[C@@H](C\C=C/CCCC(O)=O)[C@@H](O)CC1=O BHMBVRSPMRCCGG-OUTUXVNYSA-N 0.000 description 1
- 210000002307 prostate Anatomy 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 102220202301 rs76186865 Human genes 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 210000004881 tumor cell Anatomy 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
- 238000010792 warming Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/20—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals substituted additionally by nitrogen atoms, e.g. tryptophane
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/872,156 US6824760B2 (en) | 2001-06-04 | 2001-06-04 | Imaging agents, precursors thereof and methods of manufacture |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TWI244925B true TWI244925B (en) | 2005-12-11 |
Family
ID=25358962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW091111997A TWI244925B (en) | 2001-06-04 | 2002-06-04 | New imaging agents, precursors thereof and methods of manufacture |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US6824760B2 (enExample) |
| JP (1) | JP2003064046A (enExample) |
| KR (1) | KR100483650B1 (enExample) |
| CN (1) | CN1234680C (enExample) |
| TW (1) | TWI244925B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060115426A1 (en) * | 2004-08-11 | 2006-06-01 | Weichert Jamey P | Methods of detecting breast cancer, brain cancer, and pancreatic cancer |
| US8845999B2 (en) * | 2005-05-23 | 2014-09-30 | The Regents Of The University Of California | Tracers for monitoring the activity of sodium/glucose cotransporters in health and disease |
| EP2046686A1 (en) * | 2006-08-03 | 2009-04-15 | Hammersmith Imanet, Ltd | Fluoride drying method |
| WO2012025464A1 (en) | 2010-08-24 | 2012-03-01 | Bayer Pharma Aktiengesellschaft | Fluorodeuteriomethyl tyrosine derivatives |
| GB201021530D0 (en) * | 2010-12-20 | 2011-02-02 | Ge Healthcare Ltd | Purification of precursor compound by crystallisation |
| EP2520557A1 (en) * | 2011-05-03 | 2012-11-07 | Bayer Pharma Aktiengesellschaft | Novel precursors of glutamate derivatives |
| WO2015152128A1 (ja) * | 2014-03-31 | 2015-10-08 | 長瀬産業株式会社 | アミノ酸前駆体、アミノ酸およびその製造方法、ならびに該アミノ酸を用いたpet診断用トレーサー |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3800302A1 (de) * | 1988-01-08 | 1989-07-27 | Kernforschungsanlage Juelich | Radiohalogentyrosinderivate, deren herstellung und verwendung |
-
2001
- 2001-06-04 US US09/872,156 patent/US6824760B2/en not_active Expired - Fee Related
-
2002
- 2002-06-03 JP JP2002161471A patent/JP2003064046A/ja active Pending
- 2002-06-04 TW TW091111997A patent/TWI244925B/zh not_active IP Right Cessation
- 2002-06-04 KR KR10-2002-0031228A patent/KR100483650B1/ko not_active Expired - Fee Related
- 2002-06-04 CN CNB02122255XA patent/CN1234680C/zh not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US6824760B2 (en) | 2004-11-30 |
| KR100483650B1 (ko) | 2005-04-18 |
| CN1234680C (zh) | 2006-01-04 |
| CN1401629A (zh) | 2003-03-12 |
| US20030124059A1 (en) | 2003-07-03 |
| KR20020092818A (ko) | 2002-12-12 |
| JP2003064046A (ja) | 2003-03-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2700234T3 (es) | Inhibidores marcados del antígeno de membrana específico de la próstata (PSMA), evaluación biológica y uso como agentes para la obtención de imágenes | |
| US10500292B2 (en) | PSMA-binding agents and uses thereof | |
| JP5743372B2 (ja) | 放射性標識法 | |
| JP6661010B2 (ja) | ペプチドチオ尿素誘導体、これを含有する放射線同位体標識化合物、およびこれを活性成分として含有する前立腺癌を処置または診断するための医薬組成物 | |
| ES2610574T3 (es) | Procedimiento para producir un compuesto orgánico marcado con flúor radiactivo | |
| US11078166B2 (en) | Triazole conjugated ureas, thioureas, carbamates, and reversed carbamates for PSMA-targeted imaging agents and uses thereof | |
| CN115010629B (zh) | 前列腺特异性膜抗原抑制剂、其核素标记物及制法和应用 | |
| KR100745445B1 (ko) | 종양 영상화 화합물 | |
| CN117120428A (zh) | 一种截短型伊文思蓝修饰的成纤维细胞活化蛋白抑制剂及其制备方法和应用 | |
| TW202241527A (zh) | 雙模放射性追蹤劑及治療方法 | |
| TWI244925B (en) | New imaging agents, precursors thereof and methods of manufacture | |
| Bartholomä et al. | Effect of the prosthetic group on the pharmacologic properties of 18F-labeled rhodamine B, a potential myocardial perfusion agent for positron emission tomography (PET) | |
| WO2024099245A1 (zh) | 一种rgd二聚体化合物及其制备方法和应用 | |
| CN102985413B (zh) | 三羰基锝-99m或铼-188标记的环RGD衍生物、其制备方法和包含所述衍生物作为活性成分用于诊断或治疗血管发生相关疾病的药物组合物 | |
| CN118119581A (zh) | 放射性药物、其生产方法以及在疾病治疗、诊断和成像中的用途 | |
| US11426395B2 (en) | PSMA inhibitor derivatives for labelling with 99mTc via HYNIC, a radiopharmaceutical kit, radiopharmaceutical preparations and their use in prostate cancer diagnostics | |
| WO2010063403A2 (en) | Radioisotope-labeled lysine and ornithine derivatives, their use and processes for their preparation | |
| WO2012025464A1 (en) | Fluorodeuteriomethyl tyrosine derivatives | |
| Kong et al. | Development of Tyrosine‐Based Radiotracer 99mTc‐N4‐Tyrosine for Breast Cancer Imaging | |
| JPH08508262A (ja) | 放射性同位体のためのタイプs3n2キレート剤、それらの金属錯体、及びそれらの診断及び治療への使用 | |
| JP2019085344A (ja) | 放射性フッ素標識化合物 | |
| TW202535358A (zh) | 一種fap結合化合物、金屬錯合物及其用途 | |
| TWI609875B (zh) | 用於骨掃描的化合物及其用途 | |
| Shih et al. | Synthesis and Biological Evaluation of O‐[3‐18F‐fluoropropyl]‐α‐methyl Tyrosine in Mesothelioma‐Bearing Rodents | |
| WO2014096191A1 (en) | Bis 2h-imidazole-2-thione chelating agents as ligands for radiopharmaceutical in vivo imaging |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |