JP4310187B2 - Ｘ線と核磁気共鳴との組み合わせ診断法で使用するためのイオン性及び非イオン性ｘ線写真造影剤 - Google Patents
Ｘ線と核磁気共鳴との組み合わせ診断法で使用するためのイオン性及び非イオン性ｘ線写真造影剤 Download PDFInfo
- Publication number
- JP4310187B2 JP4310187B2 JP2003518618A JP2003518618A JP4310187B2 JP 4310187 B2 JP4310187 B2 JP 4310187B2 JP 2003518618 A JP2003518618 A JP 2003518618A JP 2003518618 A JP2003518618 A JP 2003518618A JP 4310187 B2 JP4310187 B2 JP 4310187B2
- Authority
- JP
- Japan
- Prior art keywords
- diagnostic
- iopamidol
- mri
- compounds
- ionic
- 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.)
- Expired - Fee Related
Links
- 239000002872 contrast media Substances 0.000 title claims abstract description 39
- 238000005481 NMR spectroscopy Methods 0.000 title abstract description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 36
- XQZXYNRDCRIARQ-LURJTMIESA-N iopamidol Chemical compound C[C@H](O)C(=O)NC1=C(I)C(C(=O)NC(CO)CO)=C(I)C(C(=O)NC(CO)CO)=C1I XQZXYNRDCRIARQ-LURJTMIESA-N 0.000 claims description 27
- 229960004647 iopamidol Drugs 0.000 claims description 27
- 238000002595 magnetic resonance imaging Methods 0.000 claims description 24
- 238000012546 transfer Methods 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 14
- 230000005415 magnetization Effects 0.000 claims description 13
- 238000009472 formulation Methods 0.000 claims description 11
- 230000005291 magnetic effect Effects 0.000 claims description 11
- 238000003384 imaging method Methods 0.000 claims description 10
- 238000001727 in vivo Methods 0.000 claims description 10
- 238000000338 in vitro Methods 0.000 claims description 8
- 238000012307 MRI technique Methods 0.000 claims description 6
- 239000002502 liposome Substances 0.000 claims description 4
- 238000009608 myelography Methods 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 238000007487 urography Methods 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 238000003745 diagnosis Methods 0.000 claims description 3
- 238000002586 coronary angiography Methods 0.000 claims description 2
- 230000002093 peripheral effect Effects 0.000 claims description 2
- 238000011835 investigation Methods 0.000 claims 3
- 230000000996 additive effect Effects 0.000 claims 1
- 230000000747 cardiac effect Effects 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 49
- 238000000034 method Methods 0.000 description 21
- 239000000243 solution Substances 0.000 description 19
- 150000001408 amides Chemical group 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- 238000002059 diagnostic imaging Methods 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- 210000000056 organ Anatomy 0.000 description 7
- 230000007423 decrease Effects 0.000 description 6
- 238000002405 diagnostic procedure Methods 0.000 description 6
- 125000005113 hydroxyalkoxy group Chemical group 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- BAQCROVBDNBEEB-UBYUBLNFSA-N Metrizamide Chemical compound CC(=O)N(C)C1=C(I)C(NC(C)=O)=C(I)C(C(=O)N[C@@H]2[C@H]([C@H](O)[C@@H](CO)OC2O)O)=C1I BAQCROVBDNBEEB-UBYUBLNFSA-N 0.000 description 5
- 241000699666 Mus <mouse, genus> Species 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229960002603 iopromide Drugs 0.000 description 5
- DGAIEPBNLOQYER-UHFFFAOYSA-N iopromide Chemical compound COCC(=O)NC1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)N(C)CC(O)CO)=C1I DGAIEPBNLOQYER-UHFFFAOYSA-N 0.000 description 5
- 229960000554 metrizamide Drugs 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000002583 angiography Methods 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- ZEYOIOAKZLALAP-UHFFFAOYSA-M sodium amidotrizoate Chemical compound [Na+].CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C([O-])=O)=C1I ZEYOIOAKZLALAP-UHFFFAOYSA-M 0.000 description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 3
- 150000001720 carbohydrates Chemical group 0.000 description 3
- 238000012631 diagnostic technique Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- -1 ioxirane Chemical compound 0.000 description 3
- MIKKOBKEXMRYFQ-WZTVWXICSA-N meglumine amidotrizoate Chemical compound C[NH2+]C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C([O-])=O)=C1I MIKKOBKEXMRYFQ-WZTVWXICSA-N 0.000 description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 2
- OIVLITBTBDPEFK-UHFFFAOYSA-N 5,6-dihydrouracil Chemical compound O=C1CCNC(=O)N1 OIVLITBTBDPEFK-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 2
- 239000002616 MRI contrast agent Substances 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- YVPYQUNUQOZFHG-UHFFFAOYSA-N amidotrizoic acid Chemical compound CC(=O)NC1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I YVPYQUNUQOZFHG-UHFFFAOYSA-N 0.000 description 2
- 235000001014 amino acid Nutrition 0.000 description 2
- 229940024606 amino acid Drugs 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 2
- 125000003636 chemical group Chemical group 0.000 description 2
- HZHFFEYYPYZMNU-UHFFFAOYSA-K gadodiamide Chemical compound [Gd+3].CNC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC(=O)NC HZHFFEYYPYZMNU-UHFFFAOYSA-K 0.000 description 2
- VVDGWALACJEJKG-UHFFFAOYSA-N iodamide Chemical compound CC(=O)NCC1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I VVDGWALACJEJKG-UHFFFAOYSA-N 0.000 description 2
- 229960004901 iodamide Drugs 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 230000005298 paramagnetic effect Effects 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 238000000079 presaturation Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 210000003462 vein Anatomy 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
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 1
- CORFWQGVBFFZHF-UHFFFAOYSA-N 2-iodohippuric acid Chemical compound OC(=O)CNC(=O)C1=CC=CC=C1I CORFWQGVBFFZHF-UHFFFAOYSA-N 0.000 description 1
- QXXSPCOLSLNNNE-UHFFFAOYSA-N 3,5-diiodo-1-methyl-4-oxopyridine-2,6-dicarboxylic acid Chemical compound CN1C(C(O)=O)=C(I)C(=O)C(I)=C1C(O)=O QXXSPCOLSLNNNE-UHFFFAOYSA-N 0.000 description 1
- LDCYZAJDBXYCGN-VIFPVBQESA-N 5-hydroxy-L-tryptophan Chemical compound C1=C(O)C=C2C(C[C@H](N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-VIFPVBQESA-N 0.000 description 1
- 229940000681 5-hydroxytryptophan Drugs 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
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 238000000685 Carr-Purcell-Meiboom-Gill pulse sequence Methods 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- UXIGWFXRQKWHHA-UHFFFAOYSA-N Iotalamic acid Chemical compound CNC(=O)C1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I UXIGWFXRQKWHHA-UHFFFAOYSA-N 0.000 description 1
- AMDBBAQNWSUWGN-UHFFFAOYSA-N Ioversol Chemical compound OCCN(C(=O)CO)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I AMDBBAQNWSUWGN-UHFFFAOYSA-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
- 229930064664 L-arginine Natural products 0.000 description 1
- 235000014852 L-arginine Nutrition 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- KTVKGXZZBQCBGD-UHFFFAOYSA-M Tyropanoate sodium Chemical compound [Na+].CCCC(=O)NC1=C(I)C=C(I)C(CC(CC)C([O-])=O)=C1I KTVKGXZZBQCBGD-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127219 anticoagulant drug Drugs 0.000 description 1
- 238000002584 aortography Methods 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 235000009697 arginine Nutrition 0.000 description 1
- 229960003121 arginine Drugs 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 229960002319 barbital Drugs 0.000 description 1
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 210000000481 breast Anatomy 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000013155 cardiography Methods 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 229940039231 contrast media Drugs 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229960005423 diatrizoate Drugs 0.000 description 1
- 229960005223 diatrizoic acid Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical class CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
- 230000003292 diminished effect Effects 0.000 description 1
- PVBALTLWZVEAIO-UHFFFAOYSA-N diodone Chemical compound OC(=O)CN1C=C(I)C(=O)C(I)=C1 PVBALTLWZVEAIO-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 210000001723 extracellular space Anatomy 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- LGMLJQFQKXPRGA-VPVMAENOSA-K gadopentetate dimeglumine Chemical compound [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O LGMLJQFQKXPRGA-VPVMAENOSA-K 0.000 description 1
- RYHQMKVRYNEBNJ-BMWGJIJESA-K gadoterate meglumine Chemical compound [Gd+3].CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 RYHQMKVRYNEBNJ-BMWGJIJESA-K 0.000 description 1
- GFSTXYOTEVLASN-UHFFFAOYSA-K gadoteric acid Chemical compound [Gd+3].OC(=O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 GFSTXYOTEVLASN-UHFFFAOYSA-K 0.000 description 1
- DPNNNPAKRZOSMO-UHFFFAOYSA-K gadoteridol Chemical compound [Gd+3].CC(O)CN1CCN(CC([O-])=O)CCN(CC([O-])=O)CCN(CC([O-])=O)CC1 DPNNNPAKRZOSMO-UHFFFAOYSA-K 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 210000002216 heart Anatomy 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 description 1
- 238000012623 in vivo measurement Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 229960004108 iobitridol Drugs 0.000 description 1
- YLPBXIKWXNRACS-UHFFFAOYSA-N iobitridol Chemical compound OCC(O)CN(C)C(=O)C1=C(I)C(NC(=O)C(CO)CO)=C(I)C(C(=O)N(C)CC(O)CO)=C1I YLPBXIKWXNRACS-UHFFFAOYSA-N 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- DGIAUNUPXILTJW-VRWDCWMNSA-N iodipamide dimeglumine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC(=O)C1=C(I)C=C(I)C(NC(=O)CCCCC(=O)NC=2C(=C(C(O)=O)C(I)=CC=2I)I)=C1I DGIAUNUPXILTJW-VRWDCWMNSA-N 0.000 description 1
- 229960004359 iodixanol Drugs 0.000 description 1
- NBQNWMBBSKPBAY-UHFFFAOYSA-N iodixanol Chemical compound IC=1C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C(I)C=1N(C(=O)C)CC(O)CN(C(C)=O)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NBQNWMBBSKPBAY-UHFFFAOYSA-N 0.000 description 1
- 229960000780 iomeprol Drugs 0.000 description 1
- NJKDOADNQSYQEV-UHFFFAOYSA-N iomeprol Chemical compound OCC(=O)N(C)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I NJKDOADNQSYQEV-UHFFFAOYSA-N 0.000 description 1
- 229960000824 iopentol Drugs 0.000 description 1
- IUNJANQVIJDFTQ-UHFFFAOYSA-N iopentol Chemical compound COCC(O)CN(C(C)=O)C1=C(I)C(C(=O)NCC(O)CO)=C(I)C(C(=O)NCC(O)CO)=C1I IUNJANQVIJDFTQ-UHFFFAOYSA-N 0.000 description 1
- 229960000929 iotalamic acid Drugs 0.000 description 1
- 229960004537 ioversol Drugs 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 229940124280 l-arginine Drugs 0.000 description 1
- HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 238000002587 lymphangiography Methods 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- GGGDNPWHMNJRFN-UHFFFAOYSA-N metrizoic acid Chemical compound CC(=O)N(C)C1=C(I)C(NC(C)=O)=C(I)C(C(O)=O)=C1I GGGDNPWHMNJRFN-UHFFFAOYSA-N 0.000 description 1
- 229960004712 metrizoic acid Drugs 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 231100001224 moderate toxicity Toxicity 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 125000003835 nucleoside group Chemical group 0.000 description 1
- 239000003605 opacifier Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- LDCYZAJDBXYCGN-UHFFFAOYSA-N oxitriptan Natural products C1=C(O)C=C2C(CC(N)C(O)=O)=CNC2=C1 LDCYZAJDBXYCGN-UHFFFAOYSA-N 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003212 purines Chemical class 0.000 description 1
- 238000002601 radiography Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000002207 retinal effect Effects 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229960003037 sodium tyropanoate Drugs 0.000 description 1
- 239000007787 solid Chemical class 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000000264 spin echo pulse sequence Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229940104230 thymidine Drugs 0.000 description 1
- 238000003325 tomography Methods 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
Images
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
- A61K49/18—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes
- A61K49/1806—Suspensions, emulsions, colloids, dispersions
- A61K49/1812—Suspensions, emulsions, colloids, dispersions liposomes, polymersomes, e.g. immunoliposomes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/04—X-ray contrast preparations
- A61K49/0433—X-ray contrast preparations containing an organic halogenated X-ray contrast-enhancing agent
- A61K49/0447—Physical forms of mixtures of two different X-ray contrast-enhancing agents, containing at least one X-ray contrast-enhancing agent which is a halogenated organic compound
- A61K49/0461—Dispersions, colloids, emulsions or suspensions
- A61K49/0466—Liposomes, lipoprotein vesicles, e.g. HDL or LDL lipoproteins, phospholipidic or polymeric micelles
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Chemical & Material Sciences (AREA)
- Dispersion Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Radiology & Medical Imaging (AREA)
- Immunology (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2001MI001706A ITMI20011706A1 (it) | 2001-08-03 | 2001-08-03 | Agenti di contrasto radiografici ionici e non ionici, utilizzabili per l'indagine diagnostica combinata tramite raggi-x e risonanza magnetic |
| PCT/EP2002/008183 WO2003013616A1 (en) | 2001-08-03 | 2002-07-23 | Ionic and non-ionic radiographic contrast agents for use in combined x-ray and nuclear magnetic resonance diagnostics |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005505527A JP2005505527A (ja) | 2005-02-24 |
| JP2005505527A5 JP2005505527A5 (enExample) | 2006-01-12 |
| JP4310187B2 true JP4310187B2 (ja) | 2009-08-05 |
Family
ID=11448229
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003518618A Expired - Fee Related JP4310187B2 (ja) | 2001-08-03 | 2002-07-23 | Ｘ線と核磁気共鳴との組み合わせ診断法で使用するためのイオン性及び非イオン性ｘ線写真造影剤 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8211404B2 (enExample) |
| EP (1) | EP1411992B1 (enExample) |
| JP (1) | JP4310187B2 (enExample) |
| AT (1) | ATE347912T1 (enExample) |
| DE (1) | DE60216770T2 (enExample) |
| DK (1) | DK1411992T3 (enExample) |
| ES (1) | ES2278946T3 (enExample) |
| IT (1) | ITMI20011706A1 (enExample) |
| WO (1) | WO2003013616A1 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20070015517A (ko) | 2004-03-11 | 2007-02-05 | 말린크로트, 인코포레이티드 | 요오드화된 단량체 및 이량체의 혼합물을 포함하는 ｘ-선조영제 제형 |
| DE102005028882A1 (de) * | 2005-06-22 | 2007-01-04 | Siemens Ag | Lösung und Verfahren zum Unterstützen der Bildgebung an einem Patienten |
| US7683617B2 (en) * | 2005-07-21 | 2010-03-23 | Johns Hopkins University | Non-invasive MRI measurement of tissue glycogen |
| US20100121188A1 (en) * | 2006-10-10 | 2010-05-13 | Sandhu Gurpreet S | Reducing contrast agent-induced toxicity |
| EP2200971B1 (en) * | 2007-10-12 | 2013-04-24 | GE Healthcare AS | Contrast agents |
| WO2009060021A1 (en) * | 2007-11-07 | 2009-05-14 | Ge Healthcare As | Contrast agents |
| DE102007058220A1 (de) | 2007-12-03 | 2009-06-04 | Bayer Schering Pharma Aktiengesellschaft | Dimere macrocyclisch substituierte Benzolderivate |
| EP2231200A1 (en) * | 2007-12-05 | 2010-09-29 | GE Healthcare AS | Contrast agents |
| EP2245003A2 (en) * | 2008-02-27 | 2010-11-03 | GE Healthcare AS | Contrast agents |
| EP2243767A1 (en) * | 2009-04-21 | 2010-10-27 | Bracco Imaging S.p.A | Process for the iodination of aromatic compounds |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2541272A1 (fr) * | 1983-02-23 | 1984-08-24 | Guerbet Sa | Composes bromes et produits opacifiants en contenant |
| CA2187427A1 (en) | 1995-02-24 | 1996-08-29 | Herve Tournier | Liposome suspensions as blood pool imaging contrast agents |
| US5648536A (en) * | 1995-06-07 | 1997-07-15 | Dunn; Thomas Jeffrey | Process for producing ioversol |
| DE69920425T2 (de) | 1998-04-09 | 2005-09-29 | Amersham Health As | Verwendung von teilchenförmigen kontrastmitteln in der diagnostischen bilderzeugung zur untersuchung physiologischer parameter |
| EP1178837A2 (en) * | 1999-04-21 | 2002-02-13 | THE GOVERNMENT OF THE UNITED STATES OF AMERICA, as represented by THE SECRETARY, DEPARTMENT OF HEALTH AND HUMAN SERVICES | Method for enhancing contrast produced by mri |
| FR2794744B1 (fr) * | 1999-06-09 | 2001-09-21 | Guerbet Sa | Complexes metalliques de polyaminoacides bicycliques, leur procede de preparation et leur application en imagerie medicale |
-
2001
- 2001-08-03 IT IT2001MI001706A patent/ITMI20011706A1/it unknown
-
2002
- 2002-07-23 US US10/485,878 patent/US8211404B2/en not_active Expired - Fee Related
- 2002-07-23 AT AT02758379T patent/ATE347912T1/de active
- 2002-07-23 EP EP02758379A patent/EP1411992B1/en not_active Expired - Lifetime
- 2002-07-23 DK DK02758379T patent/DK1411992T3/da active
- 2002-07-23 ES ES02758379T patent/ES2278946T3/es not_active Expired - Lifetime
- 2002-07-23 JP JP2003518618A patent/JP4310187B2/ja not_active Expired - Fee Related
- 2002-07-23 WO PCT/EP2002/008183 patent/WO2003013616A1/en not_active Ceased
- 2002-07-23 DE DE60216770T patent/DE60216770T2/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JP2005505527A (ja) | 2005-02-24 |
| US8211404B2 (en) | 2012-07-03 |
| DE60216770D1 (de) | 2007-01-25 |
| ATE347912T1 (de) | 2007-01-15 |
| ES2278946T3 (es) | 2007-08-16 |
| US20050113675A1 (en) | 2005-05-26 |
| ITMI20011706A1 (it) | 2003-02-03 |
| EP1411992A1 (en) | 2004-04-28 |
| DK1411992T3 (da) | 2007-04-10 |
| WO2003013616A1 (en) | 2003-02-20 |
| DE60216770T2 (de) | 2007-04-12 |
| WO2003013616A8 (en) | 2004-04-08 |
| ITMI20011706A0 (it) | 2001-08-03 |
| EP1411992B1 (en) | 2006-12-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5324503A (en) | Iodo-phenylated chelates for x-ray contrast | |
| JP2548436B2 (ja) | Ｎｍｒ−診断剤 | |
| US6278893B1 (en) | Method of magnetic resonance imaging of a sample with ex vivo polarization of an MR imaging agent | |
| US5362478A (en) | Magnetic resonance imaging with fluorocarbons encapsulated in a cross-linked polymeric shell | |
| JP4310187B2 (ja) | Ｘ線と核磁気共鳴との組み合わせ診断法で使用するためのイオン性及び非イオン性ｘ線写真造影剤 | |
| CA2349342C (en) | Manganese compositions and methods for mri | |
| US8518373B2 (en) | Ionic and non-ionic radiographic contrast agents for use in combined X-ray and nuclear magnetic resonance diagnostics | |
| JP2007528424A (ja) | ヨウ化単量体および二量体の混合物を含むｘ線造影剤製剤 | |
| Schmitz et al. | Evaluation of gadobutrol in a rabbit model as a new lanthanide contrast agent for computed tomography | |
| DE10231799B4 (de) | Verwendung von perfluoralkylhaltigen Metallkomplexen als Kontrastmittel im MR-Imaging zur Darstellung von Intravasalen Thromben | |
| US20050053551A1 (en) | Use of a combination of gadolinium-based contrast media and iodinated contrast media as a contrast agent for X-ray based medical imaging procedures | |
| JP4614281B2 (ja) | 磁気共鳴撮像方法並びに該方法に用いられる化合物 | |
| JP2001518454A (ja) | 壊死および梗塞のイメージングのための親油性金属錯体 | |
| EP0948361B1 (en) | Magnetic resonance blood pool agents | |
| TW200810782A (en) | Use of perfluoroalkyl-containing metal complexes as contrast media for diagnosis of Alzheimer's disease | |
| Janzen et al. | Aminoxyl radicals as MRI contrast agents | |
| Zheng et al. | PEGylated liposome co-encapsulating iohexol and gadoteridol for multimodal CT and MR imaging | |
| KR20250158760A (ko) | 콜라겐 및 피브린 영상화를 위한 조영제 | |
| Kim et al. | Gadolinium as a CT contrast agent: an experimental study for the effects of injection parameters in the rabbit brain model | |
| JPH03284629A (ja) | Ｍｒｉ用造影剤 | |
| JP2001519761A (ja) | ヒト血清アルブミンに結合させた磁気共鳴血液プール剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050722 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050722 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20050725 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20080930 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20081216 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20081224 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20090130 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20090206 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20090227 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20090306 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090330 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20090428 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20090511 |
|
| R150 | Certificate of patent or registration of utility model |
Ref document number: 4310187 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120515 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120515 Year of fee payment: 3 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130515 Year of fee payment: 4 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140515 Year of fee payment: 5 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |