JP5847003B2 - 18f標識化化合物 - Google Patents
18f標識化化合物 Download PDFInfo
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- JP5847003B2 JP5847003B2 JP2012088750A JP2012088750A JP5847003B2 JP 5847003 B2 JP5847003 B2 JP 5847003B2 JP 2012088750 A JP2012088750 A JP 2012088750A JP 2012088750 A JP2012088750 A JP 2012088750A JP 5847003 B2 JP5847003 B2 JP 5847003B2
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- 150000001875 compounds Chemical class 0.000 title claims description 83
- 125000004432 carbon atom Chemical group C* 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 238000003682 fluorination reaction Methods 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000005208 trialkylammonium group Chemical group 0.000 claims description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 230000015572 biosynthetic process Effects 0.000 description 26
- 238000003786 synthesis reaction Methods 0.000 description 26
- 239000000243 solution Substances 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 108090000765 processed proteins & peptides Proteins 0.000 description 12
- 235000018102 proteins Nutrition 0.000 description 12
- 102000004169 proteins and genes Human genes 0.000 description 12
- 108090000623 proteins and genes Proteins 0.000 description 12
- 239000002904 solvent Substances 0.000 description 10
- 239000012043 crude product Substances 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- BSEKZMOBPPOFFB-UHFFFAOYSA-N 3a,4,7,7a-tetrahydro-octahydro-1h-4,7-epoxyisoindole-1,3-dione Chemical compound O1C2C3C(=O)NC(=O)C3C1C=C2 BSEKZMOBPPOFFB-UHFFFAOYSA-N 0.000 description 5
- 239000012300 argon atmosphere Substances 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 238000010511 deprotection reaction Methods 0.000 description 4
- 230000014759 maintenance of location Effects 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003957 anion exchange resin Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 3
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 3
- 238000002372 labelling Methods 0.000 description 3
- QTKAQJWFVXPIFV-YFKPBYRVSA-N methyl (2r)-2-acetamido-3-sulfanylpropanoate Chemical compound COC(=O)[C@H](CS)NC(C)=O QTKAQJWFVXPIFV-YFKPBYRVSA-N 0.000 description 3
- 230000001766 physiological effect Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
- AUFVJZSDSXXFOI-UHFFFAOYSA-N 2.2.2-cryptand Chemical compound C1COCCOCCN2CCOCCOCCN1CCOCCOCC2 AUFVJZSDSXXFOI-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000005698 Diels-Alder reaction Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 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 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- KRHYYFGTRYWZRS-BJUDXGSMSA-M fluorine-18(1-) Chemical compound [18F-] KRHYYFGTRYWZRS-BJUDXGSMSA-M 0.000 description 2
- 150000002240 furans Chemical class 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- -1 nitrobenzenesulfonyl group Chemical group 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 102000004196 processed proteins & peptides Human genes 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- 238000003325 tomography Methods 0.000 description 2
- 0 *CCOCCOCCF Chemical compound *CCOCCOCCF 0.000 description 1
- KCONMNWPRXAWKK-UHFFFAOYSA-N 2-[2-[2-(4-methylphenyl)sulfonyloxyethoxy]ethoxy]ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCOCCOCCOS(=O)(=O)C1=CC=C(C)C=C1 KCONMNWPRXAWKK-UHFFFAOYSA-N 0.000 description 1
- 125000004791 2-fluoroethoxy group Chemical group FCCO* 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZIHFPOOMRISWMR-UHFFFAOYSA-N C1=CC(=O)N(C1=O)CCOCCOCCF Chemical compound C1=CC(=O)N(C1=O)CCOCCOCCF ZIHFPOOMRISWMR-UHFFFAOYSA-N 0.000 description 1
- ZIHFPOOMRISWMR-KXMUYVCJSA-N C1=CC(=O)N(C1=O)CCOCCOCC[18F] Chemical compound C1=CC(=O)N(C1=O)CCOCCOCC[18F] ZIHFPOOMRISWMR-KXMUYVCJSA-N 0.000 description 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N COC(c1ccccc1)=O Chemical compound COC(c1ccccc1)=O QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- ORSWGYZTIQNFPT-UHFFFAOYSA-N NCCOCCOCC[N+]([O-])=O Chemical compound NCCOCCOCC[N+]([O-])=O ORSWGYZTIQNFPT-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- CBKHOGXLEFSEGB-UHFFFAOYSA-N O=C(c1c(C2)ccc2c11)N(CCOCCOCCF)C1=O Chemical compound O=C(c1c(C2)ccc2c11)N(CCOCCOCCF)C1=O CBKHOGXLEFSEGB-UHFFFAOYSA-N 0.000 description 1
- FLPYEIFCSKVDIM-UHFFFAOYSA-N O=C(c1c(cc2)[o]c2c11)NC1=O Chemical compound O=C(c1c(cc2)[o]c2c11)NC1=O FLPYEIFCSKVDIM-UHFFFAOYSA-N 0.000 description 1
- ABBHMHQHNNVGSZ-UHFFFAOYSA-N [O-][N+](CCOCCOCCO)=O Chemical compound [O-][N+](CCOCCOCCO)=O ABBHMHQHNNVGSZ-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- YCKRFDGAMUMZLT-BJUDXGSMSA-N fluorine-18 atom Chemical compound [18F] YCKRFDGAMUMZLT-BJUDXGSMSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 238000009206 nuclear medicine Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical group CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical group CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Description
(式(II)中、R1及びR2はそれぞれ独立にH又は炭素数1〜24のアルキル基を示し、R3及びR4はそれぞれ独立にH又は炭素数1〜6のアルキル基を示し、Q1は、18F又は式(1)で表される基を示し、nは1〜8の整数を示す。)
(式(III)中、R1及びR2はそれぞれ独立にH又は炭素数1〜24のアルキル基を示し、R3及びR4はそれぞれ独立にH又は炭素数1〜6のアルキル基を示し、Q2は、置換スルホニル基、ハロゲン原子又は式(2)で表される基を示し、nは1〜8の整数を示す。
(式(2)中、Q3は、炭素数1〜4のトリアルキルアンモニウム基、−NO2又はハロゲン原子を示す。))
4,7,13,16,21,24−ヘキサオキサ−1,10−ジアザビシクロ[8.8.8]ヘキサコサン(K[2.2.2])及び炭酸カリウム・1.5H2OはMerck社(Darmstadt,Germany)より購入した。アセトニトリル(無水)はAldrich社(Milwaukee,USA)より購入した。陰イオン交換樹脂AG1−X8(OH−form,100−200mesh)はBio−Rad Laboratories社(Hercules,USA)より購入した。その他の試薬及び溶媒は全て分析グレードを使用し、特に記載が無ければそのまま使用した。標識化合物はCUPIDシステム(住友重機械工業,東京)により合成した。
1H NMR (δ,CDCl3) 2.45(s,6H),3.53(s,4H),3.65(t,4H,J=4.0Hz),4.14(t,4H,J=4.0Hz),7.34(d,4H,J=8.0Hz),7.79(d,4H,J=8.0Hz)。
1H NMR (δ,DMSO−d6)2.42(s,3H),3.45−3.50(m,4H),3.57(t,2H,J=4.0Hz),3.62(dt,2H,J=4.0,28Hz),4.11(t,2H,J=4.0Hz),4.50(dt,2H,J=4.0,48Hz),7.48(d,2H,J=8.0Hz),7.79(d,2H,J=8.0Hz)。
1H NMR (δ,CDCl3) 2.90(s,2H),5.32(s,4H),6.53(s,2H),7.98(br,1H)。
合成スキーム(F)に従って、化合物7を合成した。以下に詳細を示す。
1H NMR (δ,DMSO−d6) 2.42(s,3H),2.93(s,2H),3.41−4.09(m,10H),5.12(s,2H),6.55(s,2H),7.48(d,2H,J=8.0Hz),7.78(d,2H,J=8.0Hz)。
MS (FAB) m/z: 452(M+H)。
HRMS (FAB) m/z: calcd for C21H26O8S (M+H): 452.1379; Found:452.1376。
合成スキーム(G)に従って、化合物8を合成した。以下に詳細を示す。
1H NMR (δ,CDCl3) 2.86(s,2H),3.77−3.60(m,10H),4.55(dt,2H,J=4.0,48Hz),5.26(s,2H),6.51(s,2H)。
MS (FAB) m/z: 300 (M+H)。
HRMS (FAB) m/z: calcd for C14H19FNO5 (M+H): 300.1247; Found:300.1240。
1H NMR (δ,CDCl3) 3.63−3.76(m,10H),4.54(dt,2H,J=4.0,48Hz),6.70(s,2H)。
MS (FAB) m/z: 232 (M+H)。
HRMS (FAB) m/z: calcd for C10H15FNO4 (M+H): 232.0985; Found:232.0990。
[18F]Fluorideはサイクロトロン(HM−18,住友重機械工業,東京)で加速した陽子ビームを[18O]H2Oに照射し、18O(p,n)18F核反応により製造した。[18F]Fluorideを陰イオン交換樹脂(AG1−X8,Bio−Rad)で吸着後、40mMのK2CO3溶液(0.5mL)で陰イオン交換樹脂より溶出した。この溶出液にK[2.2.2](15mg)をアセトニトリル(2mL)に溶解した溶液を加えた。He気流下(400mL/min)で110oCで5分間共沸脱水により水分を除去した。さらに、残渣にアセトニトリル(1mL)を加えて共沸脱水を2度繰り返した。その後、残渣を減圧下で1分間乾燥した。最後にHe気流(50mL/min)により1分間、反応器をパージして完全に水分を除去した後,反応器を室温まで冷却して、[18F]KF/K[2.2.2]複合体を得た。
合成スキーム(I)に従って、[18F]MIP2Fを合成した。以下に詳細を示す。
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FR2841558B1 (fr) * | 2002-07-01 | 2004-08-13 | Commissariat Energie Atomique | Peptides marques ayant une affinite pour un phospholipide et utilisations |
US8435488B2 (en) * | 2009-02-27 | 2013-05-07 | Genentech, Inc. | Methods and compositions for protein labelling |
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