JP2003064046A - 新造影剤、その前駆体、及び、製造方法 - Google Patents
新造影剤、その前駆体、及び、製造方法Info
- Publication number
- JP2003064046A JP2003064046A JP2002161471A JP2002161471A JP2003064046A JP 2003064046 A JP2003064046 A JP 2003064046A JP 2002161471 A JP2002161471 A JP 2002161471A JP 2002161471 A JP2002161471 A JP 2002161471A JP 2003064046 A JP2003064046 A JP 2003064046A
- Authority
- JP
- Japan
- Prior art keywords
- group
- compound
- compound according
- formula
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims abstract description 13
- 239000002872 contrast media Substances 0.000 title abstract description 9
- 238000004519 manufacturing process Methods 0.000 title description 5
- 239000002243 precursor Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 83
- 125000006239 protecting group Chemical group 0.000 claims abstract description 21
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 7
- -1 butyroxycarbonyl Chemical group 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 12
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 9
- 238000003384 imaging method Methods 0.000 claims description 8
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 8
- 125000003865 brosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)S(*)(=O)=O 0.000 claims description 7
- 125000001736 nosyl group Chemical group S(=O)(=O)(C1=CC=C([N+](=O)[O-])C=C1)* 0.000 claims description 7
- 238000002600 positron emission tomography Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 238000002603 single-photon emission computed tomography Methods 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 206010025323 Lymphomas Diseases 0.000 claims description 2
- 206010039491 Sarcoma Diseases 0.000 claims description 2
- 210000004556 brain Anatomy 0.000 claims description 2
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- 210000003679 cervix uteri Anatomy 0.000 claims description 2
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- 210000003141 lower extremity Anatomy 0.000 claims description 2
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- 210000002784 stomach Anatomy 0.000 claims description 2
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- 230000002194 synthesizing effect Effects 0.000 claims 2
- SIVPBAOGCHMZLZ-OBTQWQRRSA-N [18F]CCCN[C@@](CC1=CC=C(C=C1)O)(C(=O)O)C Chemical compound [18F]CCCN[C@@](CC1=CC=C(C=C1)O)(C(=O)O)C SIVPBAOGCHMZLZ-OBTQWQRRSA-N 0.000 claims 1
- 206010000269 abscess Diseases 0.000 abstract description 3
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- 238000003745 diagnosis Methods 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 229940024606 amino acid Drugs 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 150000001413 amino acids Chemical class 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 206010006187 Breast cancer Diseases 0.000 description 3
- 208000026310 Breast neoplasm Diseases 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 230000002285 radioactive effect Effects 0.000 description 3
- 210000001519 tissue Anatomy 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 3
- RQFUZUMFPRMVDX-UHFFFAOYSA-N 3-Bromo-1-propanol Chemical compound OCCCBr RQFUZUMFPRMVDX-UHFFFAOYSA-N 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-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
- 238000003556 assay Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000009206 nuclear medicine Methods 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
- 239000000377 silicon dioxide Substances 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- XLYOFNOQVPJJNP-NJFSPNSNSA-N ((18)O)water Chemical compound [18OH2] XLYOFNOQVPJJNP-NJFSPNSNSA-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
- 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
- 101100214874 Autographa californica nuclear polyhedrosis virus AC81 gene Proteins 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-Phenylalanine Natural products OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-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
- 101100208721 Mus musculus Usp5 gene Proteins 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
- ROHFNLRQFUQHCH-MAWXAGFGSA-N N[C@@H](CC(C)C)[11C](=O)O Chemical compound N[C@@H](CC(C)C)[11C](=O)O ROHFNLRQFUQHCH-MAWXAGFGSA-N 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- KRHYYFGTRYWZRS-BJUDXGSMSA-N ac1l2y5h Chemical compound [18FH] KRHYYFGTRYWZRS-BJUDXGSMSA-N 0.000 description 1
- CDUUKBXTEOFITR-UHFFFAOYSA-N alpha-methylserine Natural products OCC([NH3+])(C)C([O-])=O CDUUKBXTEOFITR-UHFFFAOYSA-N 0.000 description 1
- 238000005349 anion exchange Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 230000005250 beta ray Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000017531 blood circulation Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000011161 development 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
- 238000010438 heat treatment Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229930182817 methionine Natural products 0.000 description 1
- WYJJUDJUEGRXHZ-NSHDSACASA-N methyl (2s)-2-amino-3-(4-hydroxyphenyl)-2-methylpropanoate Chemical compound COC(=O)[C@@](C)(N)CC1=CC=C(O)C=C1 WYJJUDJUEGRXHZ-NSHDSACASA-N 0.000 description 1
- LLGVQUKFXIDBNH-JTQLQIEISA-N methyl (2s)-3-(4-hydroxyphenyl)-2-(methylamino)propanoate Chemical compound COC(=O)[C@@H](NC)CC1=CC=C(O)C=C1 LLGVQUKFXIDBNH-JTQLQIEISA-N 0.000 description 1
- VRYCUUXVTGQJDB-INIZCTEOSA-N methyl (2s)-3-(4-hydroxyphenyl)-2-methyl-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate Chemical compound CC(C)(C)OC(=O)N[C@](C)(C(=O)OC)CC1=CC=C(O)C=C1 VRYCUUXVTGQJDB-INIZCTEOSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 238000007344 nucleophilic reaction Methods 0.000 description 1
- 229960005190 phenylalanine Drugs 0.000 description 1
- 239000008055 phosphate buffer solution Substances 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
- 238000001243 protein synthesis Methods 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000014616 translation Effects 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 (2)
| 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 |
| US09/872156 | 2001-06-04 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003064046A true JP2003064046A (ja) | 2003-03-05 |
| JP2003064046A5 JP2003064046A5 (enExample) | 2008-02-14 |
Family
ID=25358962
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002161471A Pending JP2003064046A (ja) | 2001-06-04 | 2002-06-03 | 新造影剤、その前駆体、及び、製造方法 |
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) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP2017078066A (ja) * | 2011-05-03 | 2017-04-27 | ピラマル イメージング ソシエテ アノニム | グルタミン酸誘導体の新規前駆体 |
Families Citing this family (5)
| 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 |
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
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2017078066A (ja) * | 2011-05-03 | 2017-04-27 | ピラマル イメージング ソシエテ アノニム | グルタミン酸誘導体の新規前駆体 |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| US6824760B2 (en) | 2004-11-30 |
| KR100483650B1 (ko) | 2005-04-18 |
| CN1234680C (zh) | 2006-01-04 |
| TWI244925B (en) | 2005-12-11 |
| CN1401629A (zh) | 2003-03-12 |
| US20030124059A1 (en) | 2003-07-03 |
| KR20020092818A (ko) | 2002-12-12 |
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