JP5725561B2 - ジエチレントリアミン五酢酸誘導体の製造方法およびジエチレントリアミン五酢酸誘導体 - Google Patents
ジエチレントリアミン五酢酸誘導体の製造方法およびジエチレントリアミン五酢酸誘導体 Download PDFInfo
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/44—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members
- C07D207/444—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5
- C07D207/448—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide
- C07D207/452—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having three double bonds between ring members or between ring members and non-ring members having two doubly-bound oxygen atoms directly attached in positions 2 and 5 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms, e.g. maleimide with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom
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- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/12—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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Description
非プロトン性溶媒中、下記式(II)で表されるジエチレントリアミン五酢酸ペンタエステルと下記式(III)で表されるハロゲン化アリル化合物を反応させる工程
過剰のハロゲン化アリル化合物(III)を除去する工程;および
溶媒中、ジエチレントリアミン五酢酸ペンタエステル(II)とハロゲン化アリル化合物(III)との反応物を塩基と反応させる工程を含むことを特徴とする。
R1〜R5はそれぞれ独立してC1-6アルキル基を示し;
Xは、−(CH2)3−または−CH2−CH=CH−を示し;
Yは、C6-12アリーレン基、−CH=CH−または−(CH2)2−を示し;
Zは、C1-6アルキレン基、アミノ基、エーテル基、カルボニル基、エステル基、アミド基、ウレア基、またはこれら2以上の基が直鎖状に連なった基を示し;
Wは、−CH=CH2、−CH≡CH、アミノ基、カルボキシ基、活性アミド基、活性エステル基またはハロゲン原子を示す。]
本発明方法では、先ず、非プロトン性溶媒中、ジエチレントリアミン五酢酸ペンタエステル(II)とハロゲン化アリル化合物(III)を反応させる。当該工程では、以下のとおり反応が進行すると考えられる。
次に、過剰のハロゲン化アリル化合物(III)を除去する。次工程においてハロゲン化アリル化合物(III)が残留していると、ジエチレントリアミン五酢酸ペンタエステル(II)とハロゲン化アリル化合物(III)との反応物へさらに反応するおそれがあり、この反応を防ぐためである。
次に、溶媒中、ジエチレントリアミン五酢酸ペンタエステル(II)とハロゲン化アリル化合物(III)との反応物を塩基と反応させる。この際、以下の転移反応が起こっていると考えられる。
FT-IR(neat,cm-1):3628,3448,3077,2981,2366,2055,1732,1446,1370,1343,1188,1029,917,856,808,733
1H-NMR(CDCl3,400MHz):δ5.80(ddt,J=16.8,10.0,6.8Hz,1H),5.08(d,J=16.8Hz,1H),5.03(dt,J=10.0,0.4Hz,1H),4.20-4.13(m,10H),3.57(s,8H),3.50(t,J=7.6Hz,1H),2.88-2.77(m,6H),2.71-2.66(m,2H),2.51(ddd,J=14.0,7.6,6.8Hz,1H),2.35(ddd,J=14.0,7.6,6.8Hz,1H),1.285(t,J=6.8Hz,12H),1.276(t,J=6.8Hz,3H)
13C-NMR(CDCl3,100MHz):δ172.2(C),170.9(C×4),134.9(CH),116.5(CH2),63.6(CH),60.2(CH2×4),60.0(CH2),55.1(CH2×4),53.3(CH2×2),50.2(CH2×2),34.3(CH2×2),14.3(CH3),14.1(CH3×4)
EI-HRMS:m/z(M+H+) 計算値(C27H48N3O10):574.3340,実測値:574.3331
(1) t−ブチル [2−(4−ヨードフェニル)エチル]カルバメートの合成
FT-IR(neat,cm-1):3627,3393,2980,2937,2362,2056,1732,1679,1520,860,7741H-NMR(CDCl3,400MHz):δ7.26(d,J=8.0Hz,2H),7.11(d,J=8.0Hz,2H),6.40(d,J=15.6Hz,1H),6.16(dt,J=15.6,7.2Hz,1H),4.56-5.53(m,1H),4.17-4.12(m,10H),3.60-3.48(m,1H),3.55(s,8H),3.40-3.34(m,2H),2.90-2.61(m,11H),2.48(ddd,J=14.4,7.2,7.0Hz,1H),1.44(s,9H),1.264(t,J=6.8Hz,3H),1.256(t,J=6.8Hz,12H)
13C-NMR(CDCl3,100MHz):δ171.9(C),170.5(C×4),155.2(C),137.4(C),135.1(C),131.0(CH),128.3(CH×2),126.0(CH),125.6(CH×2),78.3(C),63.3(CH),59.8(CH2×4),59.6(CH2),54.8(CH2×4),52.9(CH2×2),49.8(CH2×2),41.4(CH2),35.4(CH2),33.2(CH2),27.9(CH3×3),14.0(CH3),13.8(CH3×4)
EI-HRMS:m/z(M+Na+) 計算値(C40H64N4O12Na):815.4418,実測値:815.4382
FT-IR(neat,cm-1):3627,3396,2980,2367,2054,1733,1699,1508,1164,868,810,775
1H-NMR(CDCl3,400MHz):δ7.10(s,4H),4.62-4.52(m,1H),4.18-4.11(m,10H),3.54(s,8H),3.39-3.33(m,3H),2.86-2.56(m,12H),1.80-1.56(m,4H),1.44(s,9H),1.258(t,J=7.2Hz,12H),1.250(t,J=7.2Hz,3H)
13C-NMR(CDCl3,100MHz):δ172.9(C),170.8(C×4),155.5(C),139.9(C),136.0(C),128.4(CH×2),128.2(CH×2),78.6(C),63.4(CH),60.0(CH2×4),59.7(CH2),54.9(CH2×4),53.4(CH2×2),50.0(CH2×2),41.5(CH2),35.5(CH2),34.9(CH2),29.3(CH2),28.1(CH3×3),27.9(CH2),14.1(CH3),13.9(CH3×4)
EI-HRMS:m/z(M+H+) 計算値(C40H67N4O12):795.4755,実測値:795.4746
FT-IR(KBr,cm-1):3853,3420,2955,2361,1743,1647,1418,1214,899,814,667
1H-NMR(D2O,400MHz):δ7.28(d,J=7.2Hz,2H),7.26(d,J=7.2Hz,2H),3.96(s,8H),3.56-3.53(m,1H),3.43(t,J=6.8Hz,4H),3.26(t,J=6.9Hz,2H),3.19-3.09(m,4H),2.97(t,J=6.8Hz,2H),2.67(t,J=6.8Hz,2H),1.87-1.78(m,1H),1.76-1.69(m,2H),1.64-1.58(m,1H)
13C-NMR(D2O,100MHz):δ177.8(C),171.8(C×4),143.6(C),137.1(C),132.0(CH×2),131.9(CH×2),66.2(CH),58.0(CH2×4),56.0(CH2×2),49.5(CH2×2),43.5(CH2),37.1(CH2),35.2(CH2),30.5(CH2),30.2(CH2)
ESI-HRMS:m/z(M-) 計算値(C25H37N4O10):553.2510,実測値:553.2520
FT-IR(neat,cm-1):3624,3465,3095,2981,2861,2365,1713,1515,1445,1407,1368,1190,1029,828,759,721,696
1H-NMR(CDCl3,400MHz):δ7.12-7.07(dd,J=8.4,2.4Hz,4H),6.66(s,2H),4.15(q,J=7.2Hz,8H),4.14(q,J=7.2Hz,2H),3.75-3.71(m,2H),3.54(s,8H),3.38-3.35(m,1H),2.87-2.56(m,12H),1.77-1.50(m,4H),1.26(t,J=7.2Hz,12H),1.25(t,J=7.2Hz,3H)
13C-NMR(CDCl3,100MHz):δ172.9(C),170.9(C×4),170.2(C×2),140.3(C),134.8(C),133.8(CH×2),128.5(CH×2),128.3(CH×2),63.7(CH),60.2(C×4),59.9(CH2),55.1(CH2×2),53.6(CH2×2),50.2(CH2×2),39.1(CH2),35.2(CH2),34.0(CH2),29.5(CH2),28.1(CH2),14.3(CH3),14.1(CH3×4)
ESI-HRMS:m/z(M+Na+) 計算値(C39H58N4O12Na):797.3949,実測値:797.3963
(1) ヨウ化物
1H-NMR(CDCl3,400MHz):δ4.52-4.50(m,NH,1H),4.16(q,J=7.2Hz,8H),4.13(q,J=7.2Hz,2H),3.55(s,8H),3.31(t,J=7.2Hz,1H),3.12-3.08(m,-CH2-NHBoc,2H),2.86-2.61(m,8H),1.44(s,9H),1.20-1.28(m,33H)
13C-NMR(CDCl3,100MHz):δ173.3(C),171.2(C×4),155.9(C),78.8(C),64.0(CH),60.3(CH2×4),59.9(CH2),55.2(CH2×4),53.7(CH2×2),50.4(CH2×2),40.6(CH2),30.0(CH2×2),29.5(CH2×2),29.4(CH2×2),29.2(CH2),28.4(CH3×3),26.7(CH2),26.4(CH2),14.4(CH3),14.2(CH3×4)
ESI-HRMS:m/z(M+H+) 計算値(C39H73N4O12):789.5225,実測値:789.5186
FT-IR(neat,cm-1):3300,2981,2119,1733,1653,1539,1447,1370,1195,1028,852,808,699
1H-NMR(CDCl3,400MHz):δ7.11(s,4H),5.68-5.66(m,1H),4.15(q,J=7.2Hz,8H),4.13-4.09(m,2H),3.55-3.50(m,2H),3.54(s,8H),3.39-3.36(m,1H),2.83-2.74(m,8H),2.67-2.58(m,4H),2.51(dt,J=2.8,7.2Hz,2H),2.35(t,J=7.2Hz,2H),1.95(t,J=2.8Hz,1H),1.78-1.70(m,4H),1.26(t,J=7.2Hz,12H),1.25(t,J=7.2Hz,3H)
13C-NMR(CDCl3,100MHz):δ173.1(C),171.0(C×4),170.7(C),140.3(C),136.0(C),128.52(CH×2),128.46(CH×2),82.8(C),69.1(CH),63.6(CH),60.2(CH2×4),59.9(CH2),55.1(CH2×4),53.6(CH2×2),50.2(CH2×2),40.5(CH2),35.13(CH2),35.08(CH2),35.0(CH2),29.4(CH2),28.1(CH2),14.7(CH2),14.3(CH3),14.1(CH3×4)
ESI-HRMS:m/z(M+Na+) 計算値(C40H62N4O11Na):797.4313,実測値:797.4313
(1) 3-{4-[N,N-ビス(2-{N’,N’-ビス[(エトキシカルボニル)メチル]アミノ}エチル)アミノ]4-エトキシカルボニル1-ブテン-1-イル}フェニルプロピオン酸
FT-IR(neat,cm-1):3447,2982,2937,2873,1734,1700,1653,1635,1560,1513,1465,1448,1419,1370,1345,1195,1029,970,920,853,810,733,668
1H-NMR(CDCl3,400MHz):δ7.25(d,J=8.0Hz,2H),7.12(d,J=8.0Hz,2H),6.40(d,J=16.0Hz,1H),6.15(dt,J=16.0,6.8Hz,1H),4.17-4.12(m,10H),3.55(s,8H),3.50-3.47(m,1H),2.95-2.60(m,13H),2.48(ddd,J=16.0,7.6,7.6Hz,1H),1.28-1.23(m,15H)
13C-NMR(CDCl3,100MHz):δ177.4(C),172.4(C),171.1(C×4),139.1(C),135.5(C),131.6(CH),128.2(CH×2),126.2(CH),126.1(CH×2),63.9(CH),60.3(CH2×4),60.1(CH2),55.1(CH2×4),53.3(CH2×2),50.1(CH2×2),35.4(CH2),33.5(CH2),30.3(CH2),14.3(CH3),14.1(CH3×4)
ESI-HRMS:m/z(M+H+) 計算値(C36H56N3O12):722.3864,実測値:722.3822
FT-IR(neat,cm-1):3584,3446,2981,2936,2869,1732,1515,1446,1417,1372,1347,1298,1198,1097,1027
1H-NMR(CDCl3,400MHz):δ7.12(d,J=8.4Hz,2H),7.09(d,J=8.4Hz,2H),4.15(q,J=7.2Hz,8H),4.12-4.09(m,2H),3.53(s,8H),3.32-3.29(m,1H),2.92(t,J=7.6Hz,2H),2.79-2.51(m,12H),1.70-1.48(m,4H),1.26(t,J=7.2Hz,12H),1.25(t,J=7.2Hz,3H,OCH2-CH3)
13C-NMR(CDCl3,100MHz):δ177.4(C),173.2(C),171.2(C×4),140.1(C),137.7(C),128.5(CH×2),128.2(CH×2),63.9(CH),60.4(CH2×4),60.0(CH2),55.2(CH2×4),53.6(CH2×2),50.2(CH2×2),35.7(CH2),35.2(CH2),30.4(CH2),29.5(CH2),28.2(CH2),14.4(CH3),14.2(CH3×4)
ESI-HRMS:m/z(M+H+) 計算値(C36H58N3O12):724.4021,実測値:724.4007
(1) N,N−ジ(t−ブトキシカルボニル)−O−[3−(4−ヨード)フェニル]プロピルヒドロキシルアミン
FT-IR(KBr,cm-1):3649,3462,2978,2889,2365,2341,1913,1742,1636,1617,1558,1541,1507,1488,1456,1391,1368,1315,1281,1251,1142,1118,1026,1009,907,879,837,797,747,620,507
1H-NMR(CDCl3,400MHz):δ7.60(d,J=8.4Hz,2H),6.96(d,J=8.4Hz,2H),3.93(t,J=6.2Hz,2H),2.74-2.70(m,2H),1.96-1.89(m,2H),1.53(s,18H)
13C-NMR(CDCl3,100MHz):δ150.2(C×2),141.2(C),137.4(CH×2),130.5(CH×2),90.9(C),83.7(C×2),75.2(CH2),31.8(CH2),29.7(CH2),28.1(CH3×6)
ESI-HRMS:m/z(M+Na+) 計算値(C19H28O5Na):500.0910,実測値:500.0910
FT-IR(neat,cm-1):3735,3446,2980,2938,2368,2343,1792,1732,1541,1513,1417,1456,1393,1369,1345,1276,1250,1179,1156,1116,1092,972,917,882,851,796,754,717
1H-NMR(CDCl3,400MHz):δ7.25(d,J=8.0Hz,2H),7.12(d,J=8.0Hz,2H),6.43(d,J=15.6Hz,1H),6.16(ddd,J=15.6,7.2,7.2Hz,1H),4.17-4.12(m,10H),3.95(t,J=6.4Hz,2H),3.56(s,8H),3.53-3.50(m,1H),2.90-2.61(m,11H),2.48(ddd,J=14.4,7.2,7.2Hz,1H),1.98-1.91(m,2H),1.54(s,18H),1.25(t,J=7.2Hz,15H)
13C-NMR(CDCl3,100MHz):δ172.3(C),171.0(C×4),150.0(C×2),140.28(C),135.2(C),131.5(CH),128.3(CH×2),126.0(CH),125.9(CH×2),83.5(C×2),75.5(CH2),63.9(CH),60.3(CH2×4),60.1(CH2),55.2(CH2×4),53.4(CH2×2),50.3(CH2×2),33.6(CH2),32.0(CH2),29.8(CH2),28.0(CH3×6),14.3(CH3),14.1(CH3×4)
ESI-HRMS:m/z(M+H+) 計算値(C46H75N4O15):923.5229,実測値:923.5198
FT-IR(neat,cm-1):3630,3552,3456,2980,2373,2346,2054,1902,1792,1731,1514,1456,1417,1393,1369,1344,1249,1029,917,851,796,754
1H-NMR(CDCl3,400MHz):δ7.11(d,J=8.0Hz,2H),7.08(d,J=8.0Hz,2H),4.17-4.10(m,10H),3.95(t,J=6.4Hz,2H),3.54(s,8H),3.38(t,J=6.8Hz,1H),2.86-2.56(m,12H),1.98-1.91(m,2H),1.77-1.57(m,4H),1.54(s,18H),1.26(t,J=7.2Hz,12H),1.25(t,J=7.2Hz,3H)
13C-NMR(CDCl3,100MHz):δ173.2(C),171.1(C×4),150.2(C×2),139.8(C),138.9(C),128.3(CH×2),128.2(CH×2),83.6(C×2),75.6(CH2),63.8(CH),60.4(CH2×4),60.0(CH2),55.2(CH2×4),53.7(CH2×2),50.3(CH2×2),35.2(CH2),31.9(CH2),29.9(CH2),29.7(CH2),28.3(CH2),28.0(CH3×6),14.4(CH3),14.2(CH3×4)
ESI-HRMS:m/z(M+Na+) 計算値(C46H76N4O15Na):947.5205,実測値:947.5179
FT-IR(KBr,cm-1):3567,3367,2950,2362,2359,2348,1991,1869,1845,1740,1653,1558,1516,1457,1419,1202,1113,1034,953,898,873,807,715,660,609,542,489,454
1H-NMR(D2O,400MHz):δ7.25(s,4H),4.07(t,J=6.4Hz,2H),4.03(s,8H),3.64-3.60(m,1H),3.44(t,J=6.0Hz,4H),3.20-3.12(m,4H),2.71(t,J=7.6Hz,2H),2.66(t,J=6.8Hz,2H),2.02-1.95(m,2H),1.87-1.82(m,1H),1.79-1.71(m,2H),1.70-1.61(m,1H)
13C-NMR(D2O,100MHz):δ177.7(C),172.5(C×4),142.7(C),141.9(C),131.7(CH×2),131.6(CH×2),77.6(CH2),66.3(CH),58.5(CH2×4),55.7(CH2×2),49.6(CH2×2),37.1(CH2),33.3(CH2),31.6(CH2),30.5(CH2),30.3(CH2)
ESI-HRMS:m/z(M+H+) 計算値(C26H39N4O11):583.2615,実測値:583.2599
元素分析: 計算値(C26H44N4O11Cl4・5H2O)−C:41.23,H:6.25,N:7.40, 実測値−C:41.02,H:6.37,N:7.53
Claims (6)
- 下記式(I)で表されるジエチレントリアミン五酢酸誘導体を製造するための方法であって、
[式中、R1〜R5はそれぞれ独立してC1-6アルキル基を示す]
非プロトン性溶媒中、下記式(II)で表されるジエチレントリアミン五酢酸ペンタエステルと下記式(III)で表されるハロゲン化アリル化合物を反応させる工程
[式中、R1〜R5は上記と同義を示し;Halはハロゲン原子を示す];
過剰のハロゲン化アリル化合物(III)を除去する工程;および
溶媒中、ジエチレントリアミン五酢酸ペンタエステル(II)とハロゲン化アリル化合物(III)との反応物を塩基と反応させる工程;
を含むことを特徴とする製造方法。 - ジエチレントリアミン五酢酸ペンタエステル(II)に対して7倍モル以上のハロゲン化アリル化合物(III)を反応させる請求項1に記載の製造方法。
- 塩基として、アルカリ金属またはアルカリ土類金属の炭酸塩または炭酸水素塩を用いる請求項1または2に記載の製造方法。
- 非プロトン性溶媒として、ジメチルホルムアミドまたはジメチルアセトアミドを用いる請求項1〜3のいずれかに記載の製造方法。
- 下記式(I)で表されることを特徴とするジエチレントリアミン五酢酸誘導体。
[式中、R1〜R5はそれぞれ独立してC1-6アルキル基を示す] - 下記式(IV)で表されることを特徴とするガドリニウム錯体前駆体。
R1〜R5はそれぞれ独立してC1-6アルキル基を示し;
Xは、−(CH2)3−または−CH2−CH=CH−を示し;
Yは、C6-12アリーレン基、−CH=CH−または−(CH2)2−を示し;
Zは、C1-6アルキレン基、アミノ基、エーテル基、カルボニル基、エステル基、アミド基、ウレア基、またはこれら2以上、5以下の基が直鎖状に連なった基を示し;
Wは、−CH=CH2、−CH≡CH、アミノ基、カルボキシ基、活性アミド基、活性エステル基またはハロゲン原子を示す。]
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JPH0931037A (ja) * | 1995-07-21 | 1997-02-04 | Univ Tohoku | 非エステル結合性dtpa誘導体およびその製造方法 |
JPH11501012A (ja) * | 1995-02-21 | 1999-01-26 | シェーリング アクチェンゲゼルシャフト | 新規な方法において置換されたdtpa誘導体、それらの金属錯体、これらの錯体を含有する医薬製剤、診断および治療におけるそれらの使用、ならびに錯体および医薬製剤の製造方法 |
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JPH0931037A (ja) * | 1995-07-21 | 1997-02-04 | Univ Tohoku | 非エステル結合性dtpa誘導体およびその製造方法 |
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