CA2065415A1 - Agents d'imagerie a resonance magnetique - Google Patents

Agents d'imagerie a resonance magnetique

Info

Publication number: CA2065415A1
Authority: CA; Canada
Prior art keywords: iii; alkyl; hydrogen; carbon atoms; complex
Prior art date: 1989-09-05
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.): Abandoned

Application number

CA002065415A

Other languages

English (en)

Inventor

Raghavan Rajagopalan

Muthunadar P. Periasamy

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Mallinckrodt Inc

Original Assignee

Individual

Priority date (The priority date 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 date listed.)

1989-09-05

Filing date

1990-03-05

Publication date

1991-03-06

1989-09-05 Priority claimed from US07/402,623 external-priority patent/US5011925A/en

1990-03-05 Application filed by Individual filed Critical Individual

1991-03-06 Publication of CA2065415A1 publication Critical patent/CA2065415A1/fr

Status Abandoned legal-status Critical Current

Links

239000012216 imaging agent Substances 0.000 title abstract description 4
238000002595 magnetic resonance imaging Methods 0.000 title abstract description 4
150000002500 ions Chemical class 0.000 claims abstract description 47
230000005298 paramagnetic effect Effects 0.000 claims abstract description 46
238000000034 method Methods 0.000 claims abstract description 41
238000003384 imaging method Methods 0.000 claims abstract description 20
241001465754 Metazoa Species 0.000 claims abstract description 17
238000002405 diagnostic procedure Methods 0.000 claims abstract description 4
239000000203 mixture Substances 0.000 claims description 60
229910052739 hydrogen Inorganic materials 0.000 claims description 45
125000000217 alkyl group Chemical group 0.000 claims description 44
125000004432 carbon atom Chemical group C* 0.000 claims description 42
239000008139 complexing agent Substances 0.000 claims description 39
239000001257 hydrogen Substances 0.000 claims description 39
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 27
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
229910052688 Gadolinium Inorganic materials 0.000 claims description 23
125000004103 aminoalkyl group Chemical group 0.000 claims description 23
229910052757 nitrogen Inorganic materials 0.000 claims description 23
UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 claims description 22
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
229910052692 Dysprosium Inorganic materials 0.000 claims description 15
229910052771 Terbium Inorganic materials 0.000 claims description 15
KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 claims description 15
GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 claims description 15
JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 claims description 13
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 12
SCKNFLZJSOHWIV-UHFFFAOYSA-N holmium(3+) Chemical compound [Ho+3] SCKNFLZJSOHWIV-UHFFFAOYSA-N 0.000 claims description 12
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 11
125000003282 alkyl amino group Chemical group 0.000 claims description 11
125000005001 aminoaryl group Chemical group 0.000 claims description 11
125000003118 aryl group Chemical group 0.000 claims description 11
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 claims description 10
125000004945 acylaminoalkyl group Chemical group 0.000 claims description 10
125000003545 alkoxy group Chemical group 0.000 claims description 10
229910001424 calcium ion Inorganic materials 0.000 claims description 10
125000000623 heterocyclic group Chemical group 0.000 claims description 10
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
125000001424 substituent group Chemical group 0.000 claims description 10
150000001768 cations Chemical class 0.000 claims description 9
WAEMQWOKJMHJLA-UHFFFAOYSA-N Manganese(2+) Chemical compound [Mn+2] WAEMQWOKJMHJLA-UHFFFAOYSA-N 0.000 claims description 8
VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 claims description 8
229910052777 Praseodymium Inorganic materials 0.000 claims description 8
BFGKITSFLPAWGI-UHFFFAOYSA-N chromium(3+) Chemical compound [Cr+3] BFGKITSFLPAWGI-UHFFFAOYSA-N 0.000 claims description 8
XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 claims description 8
MMIPFLVOWGHZQD-UHFFFAOYSA-N manganese(3+) Chemical compound [Mn+3] MMIPFLVOWGHZQD-UHFFFAOYSA-N 0.000 claims description 8
QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 8
PUDIUYLPXJFUGB-UHFFFAOYSA-N praseodymium atom Chemical compound [Pr] PUDIUYLPXJFUGB-UHFFFAOYSA-N 0.000 claims description 8
DOSGOCSVHPUUIA-UHFFFAOYSA-N samarium(3+) Chemical compound [Sm+3] DOSGOCSVHPUUIA-UHFFFAOYSA-N 0.000 claims description 8
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
239000000872 buffer Substances 0.000 claims description 6
231100000252 nontoxic Toxicity 0.000 claims description 6
230000003000 nontoxic effect Effects 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
JLVVSXFLKOJNIY-UHFFFAOYSA-N Magnesium ion Chemical compound [Mg+2] JLVVSXFLKOJNIY-UHFFFAOYSA-N 0.000 claims description 5
PTFCDOFLOPIGGS-UHFFFAOYSA-N Zinc dication Chemical compound [Zn+2] PTFCDOFLOPIGGS-UHFFFAOYSA-N 0.000 claims description 5
229910001431 copper ion Inorganic materials 0.000 claims description 5
239000003792 electrolyte Substances 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
229910001425 magnesium ion Inorganic materials 0.000 claims description 5
229910001415 sodium ion Inorganic materials 0.000 claims description 5
238000007911 parenteral administration Methods 0.000 claims description 4
CWYNVVGOOAEACU-UHFFFAOYSA-N Fe2+ Chemical compound [Fe+2] CWYNVVGOOAEACU-UHFFFAOYSA-N 0.000 claims description 3
229910052742 iron Inorganic materials 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims 25
229910052691 Erbium Inorganic materials 0.000 claims 14
UYAHIZSMUZPPFV-UHFFFAOYSA-N erbium Chemical compound [Er] UYAHIZSMUZPPFV-UHFFFAOYSA-N 0.000 claims 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 9
239000003937 drug carrier Substances 0.000 claims 8
229910052769 Ytterbium Inorganic materials 0.000 claims 7
NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 claims 7
229910052689 Holmium Inorganic materials 0.000 claims 3
KJZYNXUDTRRSPN-UHFFFAOYSA-N holmium atom Chemical compound [Ho] KJZYNXUDTRRSPN-UHFFFAOYSA-N 0.000 claims 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
125000004442 acylamino group Chemical group 0.000 claims 1
QPCDCPDFJACHGM-UHFFFAOYSA-N N,N-bis{2-[bis(carboxymethyl)amino]ethyl}glycine Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(=O)O)CCN(CC(O)=O)CC(O)=O QPCDCPDFJACHGM-UHFFFAOYSA-N 0.000 abstract description 12
239000002738 chelating agent Substances 0.000 abstract description 8
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 abstract description 6
125000004122 cyclic group Chemical group 0.000 abstract description 4
229960003330 pentetic acid Drugs 0.000 abstract description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
238000005481 NMR spectroscopy Methods 0.000 description 21
239000003446 ligand Substances 0.000 description 13
210000001519 tissue Anatomy 0.000 description 13
238000002360 preparation method Methods 0.000 description 11
239000002253 acid Substances 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
125000002843 carboxylic acid group Chemical group 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
150000001875 compounds Chemical class 0.000 description 9
230000005291 magnetic effect Effects 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
238000002591 computed tomography Methods 0.000 description 6
239000000706 filtrate Substances 0.000 description 6
210000000056 organ Anatomy 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000002904 solvent Substances 0.000 description 6
241000699670 Mus sp. Species 0.000 description 5
WDLRUFUQRNWCPK-UHFFFAOYSA-N Tetraxetan Chemical compound OC(=O)CN1CCN(CC(O)=O)CCN(CC(O)=O)CCN(CC(O)=O)CC1 WDLRUFUQRNWCPK-UHFFFAOYSA-N 0.000 description 5
239000007983 Tris buffer Substances 0.000 description 5
238000009472 formulation Methods 0.000 description 5
150000003839 salts Chemical class 0.000 description 5
239000007787 solid Substances 0.000 description 5
-1 Gadolinium (III) ions Chemical class 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000008367 deionised water Substances 0.000 description 4
229910021641 deionized water Inorganic materials 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000001914 filtration Methods 0.000 description 4
239000012530 fluid Substances 0.000 description 4
NDJKXXJCMXVBJW-UHFFFAOYSA-N heptadecane Chemical compound CCCCCCCCCCCCCCCCC NDJKXXJCMXVBJW-UHFFFAOYSA-N 0.000 description 4
239000012535 impurity Substances 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
230000005855 radiation Effects 0.000 description 4
229910001868 water Inorganic materials 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
RAZLJUXJEOEYAM-UHFFFAOYSA-N 2-[bis[2-(2,6-dioxomorpholin-4-yl)ethyl]azaniumyl]acetate Chemical compound C1C(=O)OC(=O)CN1CCN(CC(=O)O)CCN1CC(=O)OC(=O)C1 RAZLJUXJEOEYAM-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
230000037396 body weight Effects 0.000 description 3
239000007810 chemical reaction solvent Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000000725 suspension Substances 0.000 description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
101710184444 Complexin Proteins 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
206010030113 Oedema Diseases 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 2
239000013522 chelant Substances 0.000 description 2
230000009918 complex formation Effects 0.000 description 2
DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
230000002708 enhancing effect Effects 0.000 description 2
239000011521 glass Substances 0.000 description 2
229910001385 heavy metal Inorganic materials 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
238000002156 mixing Methods 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
230000001376 precipitating effect Effects 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
QBPPRVHXOZRESW-UHFFFAOYSA-N 1,4,7,10-tetraazacyclododecane Chemical compound C1CNCCNCCNCCN1 QBPPRVHXOZRESW-UHFFFAOYSA-N 0.000 description 1
KIUIVKNVSSLOAG-UHFFFAOYSA-N 1,4,7,10-tetrazacyclotridecan-11-one Chemical compound O=C1CCNCCNCCNCCN1 KIUIVKNVSSLOAG-UHFFFAOYSA-N 0.000 description 1
ZMBVBAVBXVSHER-UHFFFAOYSA-N 2-thiomorpholin-4-ylethanamine Chemical compound NCCN1CCSCC1 ZMBVBAVBXVSHER-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical class [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical class OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 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
241000124008 Mammalia Species 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical class CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
238000012565 NMR experiment Methods 0.000 description 1
238000011887 Necropsy Methods 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
230000002159 abnormal effect Effects 0.000 description 1
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
238000006664 bond formation reaction Methods 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
230000001427 coherent effect Effects 0.000 description 1
238000010668 complexation reaction Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000012059 conventional drug carrier Substances 0.000 description 1
150000004696 coordination complex Chemical class 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000013461 design Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
229960001484 edetic acid Drugs 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
JHFPQYFEJICGKC-UHFFFAOYSA-N erbium(3+) Chemical compound [Er+3] JHFPQYFEJICGKC-UHFFFAOYSA-N 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
210000003722 extracellular fluid Anatomy 0.000 description 1
238000003818 flash chromatography Methods 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
229940075613 gadolinium oxide Drugs 0.000 description 1
229910001938 gadolinium oxide Inorganic materials 0.000 description 1
RJOJUSXNYCILHH-UHFFFAOYSA-N gadolinium(3+) Chemical compound [Gd+3] RJOJUSXNYCILHH-UHFFFAOYSA-N 0.000 description 1
CMIHHWBVHJVIGI-UHFFFAOYSA-N gadolinium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Gd+3].[Gd+3] CMIHHWBVHJVIGI-UHFFFAOYSA-N 0.000 description 1
238000007429 general method Methods 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
101150003235 hoxY gene Proteins 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
JCYWCSGERIELPG-UHFFFAOYSA-N imes Chemical class CC1=CC(C)=CC(C)=C1N1C=CN(C=2C(=CC(C)=CC=2C)C)[C]1 JCYWCSGERIELPG-UHFFFAOYSA-N 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
125000003010 ionic group Chemical group 0.000 description 1
230000005865 ionizing radiation Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000005415 magnetization Effects 0.000 description 1
238000013507 mapping Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
230000001613 neoplastic effect Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000002405 nuclear magnetic resonance imaging agent Substances 0.000 description 1
238000001208 nuclear magnetic resonance pulse sequence Methods 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
238000001139 pH measurement Methods 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
239000012217 radiopharmaceutical Substances 0.000 description 1
229940121896 radiopharmaceutical Drugs 0.000 description 1
230000002799 radiopharmaceutical effect Effects 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
210000004872 soft tissue Anatomy 0.000 description 1
241000894007 species Species 0.000 description 1
238000002798 spectrophotometry method Methods 0.000 description 1
238000000264 spin echo pulse sequence Methods 0.000 description 1
238000005728 strengthening Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
239000008096 xylene Substances 0.000 description 1
AWSFICBXMUKWSK-UHFFFAOYSA-N ytterbium(3+) Chemical compound [Yb+3] AWSFICBXMUKWSK-UHFFFAOYSA-N 0.000 description 1

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

Landscapes

Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Radiology & Medical Imaging (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Compounds Of Iron (AREA)

CA002065415A 1989-09-05 1990-03-05 Agents d'imagerie a resonance magnetique Abandoned CA2065415A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US402,623		1989-09-05
US07/402,623 US5011925A (en)	1989-03-09	1989-09-05	Morpholinoamido EDTA derivatives

Publications (1)

Publication Number	Publication Date
CA2065415A1 true CA2065415A1 (fr)	1991-03-06

Family

ID=23592670

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA002065415A Abandoned CA2065415A1 (fr)	1989-09-05	1990-03-05	Agents d'imagerie a resonance magnetique

Country Status (5)

Country	Link
EP (1)	EP0490897A1 (fr)
JP (1)	JPH04507401A (fr)
AU (1)	AU646393B2 (fr)
CA (1)	CA2065415A1 (fr)
WO (1)	WO1991003261A1 (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5384108A (en) *	1989-04-24	1995-01-24	Mallinckrodt Medical, Inc.	Magnetic resonance imaging agents
US5077037A (en) *	1990-08-03	1991-12-31	Mallinckrodt Medical, Inc.	Novel compositions for magnetic resonance imaging
US5162109A (en) *	1990-09-13	1992-11-10	Mallinckrodt Medical, Inc.	Magnetic resonance imaging agents
AU656355B2 (en) *	1990-11-21	1995-02-02	Mallinckrodt Medical, Inc.	Alkoxyamide derivatized chelates for MRI
AU660033B2 (en) *	1991-05-23	1995-06-08	Imarx Pharmaceutical Corp.	Liposoluble compounds for magnetic resonance imaging
EP0692977B1 (fr) *	1993-03-15	1999-10-13	Mallinckrodt Inc.	Nouveau ligand base sur un heterocycle et contenant du soufre et de l'azote, utile dans les agents d'imagerie radiographique
DE19507822B4 (de) *	1995-02-21	2006-07-20	Schering Ag	Substituierte DTPA-Monoamide der zentralen Carbonsäure und deren Metallkomplexe, diese Komplexe enthaltende pharmazeutische Mittel, deren Verwendung in der Diagnostik und Therapie sowie Verfahren zur Herstellung der Komplexe und Mittel
DE19507819A1 (de) *	1995-02-21	1996-08-22	Schering Ag	DTPA-Monoamide der zentralen Carbonsäure und deren Metallkomplexe, diese Komplexe enthaltende pharmazeutische Mittel, deren Verwendung in der Diagnostik und Therapie sowie Verfahren zur Herstellung der Komplexe und Mittel
HUP1500076A2 (hu) *	2015-02-25	2016-09-28	Debreceni Egyetem	Új helyettesített etilén-diamin-tetraecetsav-bisz(amid) származékok és alkalmazásuk Mn(II)-alapú MRI kontrasztanyag ligandumként

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL194579C (nl) *	1983-01-21	2002-08-05	Schering Ag	Diagnostisch middel.
DE3324235A1 (de) *	1983-07-01	1985-01-10	Schering AG, 1000 Berlin und 4709 Bergkamen	Neue komplexbildner, komplexe und komplexsalze
US4822594A (en) *	1987-01-27	1989-04-18	Gibby Wendell A	Contrast enhancing agents for magnetic resonance images
US5137711A (en) *	1988-07-19	1992-08-11	Mallickrodt Medical, Inc.	Paramagnetic dtpa and edta alkoxyalkylamide complexes as mri agents

1990
- 1990-03-05 AU AU55351/90A patent/AU646393B2/en not_active Ceased
- 1990-03-05 JP JP2506747A patent/JPH04507401A/ja active Pending
- 1990-03-05 WO PCT/US1990/001196 patent/WO1991003261A1/fr not_active Ceased
- 1990-03-05 CA CA002065415A patent/CA2065415A1/fr not_active Abandoned
- 1990-03-05 EP EP19900907932 patent/EP0490897A1/fr not_active Ceased

Also Published As

Publication number	Publication date
JPH04507401A (ja)	1992-12-24
EP0490897A1 (fr)	1992-06-24
AU5535190A (en)	1991-04-08
WO1991003261A1 (fr)	1991-03-21
AU646393B2 (en)	1994-02-24

Legal Events

Date	Code	Title	Description
1996-09-05	FZDE	Discontinued
2023-05-26	FZDE	Discontinued	Effective date: 19960905

Publication	Publication Date	Title
US5376358A (en)	1994-12-27	Magnetic resonance imaging agents
EP0425571B2 (fr)	2000-09-20	Agents d'imagerie a resonance magnetique
US5077037A (en)	1991-12-31	Novel compositions for magnetic resonance imaging
US5141740A (en)	1992-08-25	Complexes and compositions for magnetic resonance imaging and usage methods
US5162109A (en)	1992-11-10	Magnetic resonance imaging agents
AU640140B2 (en)	1993-08-19	Novel magnetic resonance imaging agents
CA2065415A1 (fr)	1991-03-06	Agents d'imagerie a resonance magnetique
US5138040A (en)	1992-08-11	Composition for magnetic resonance imaging
US5130120A (en)	1992-07-14	Paramagnetic DTPA and EDTA alkoxyalkylamide complexes as MRI agents
US5217706A (en)	1993-06-08	Complexes and compositions for magnetic resonance imaging
AU656355B2 (en)	1995-02-02	Alkoxyamide derivatized chelates for MRI
US5290537A (en)	1994-03-01	Compositions for magnetic resonance imaging
DE19835082A1 (de)	2000-02-03	Paramagnetische 3-,8-substituierte Deuteroporphyrinderivate, diese enthaltende pharmazeutische Mittel, Verfahren zu ihrer Herstellung und ihre Verwendung für das Nekrose- und Infarkt-MR-Imaging
AU650615C (en)	1995-12-07	Novel magnetic resonance imaging agents
WO1994008630A1 (fr)	1994-04-28	Nouvelles compostions d'imagerie par resonance magnetique