Paramagnetic chelates useful for nmr imaging

Details Paramagnetic chelates useful for nmr imaging Paramagnetic chelates useful for nmr imaging

C - Chemistry, Metallurgy

07

C

260/426, 167/46,

C07C 229/26 (2006.01) A61K 31/28 (2006.01) C07C 229/36 (2006.01) C07F 5/00 (2006.01)

Patent

CA 1324150

- a - ABSTRACT OF THE DISCLOSURE Compounds suitable for NMR imaging having the formula: Image (I) wherein a is 2 or 3; b is an integer from 0 to 4; Me(a+) is Fe(2+), F2(3+), Gd(3+) or Mn(2+); E(b+) is an ion of an alkali metal, alkaline earth metal, alkyl ammonium, alkanol ammonium, polyhydroxyalkyl ammonium, or basic protonated amino acid, said ions representing a total charge of b; m is an integer from 1 to 5; R is H, alkyl with from 1 to 8 carbon atoms, alkyl with from 1 to 8 carbon atoms wherein from 1 to 5 carbons are substituted with OH; aralkyl with 1 to 4 aliphatic carbon atoms; phenyl or phenyl substituted by halogen, hydroxyl, carboxyl, carboxamide, ester, SO3H, sulfonamide, lower alkyl, lower hydroxy alkyl, amino, acylamino; (poly)oxa-alkyl with 1 to 50 oxygen atoms and from 3 to 150 carbon atoms, wherein 1 to 5 hydrogen atoms may be substituted by OH; - b - R1 is the same as R2 or is -CH2COOZ, -CH(CH3)COOZ, CH2CH2-N(CH2COOZ)2, a hydroxy arylalkyl, hydroxy pyridylalkyl, hydroxy aryl(carboxy)alkyl or hydroxy pyridyl-(carboxy)- alkyl radical, where the aryl or pyridyl radical may be substituted by hydroxyl, hydroxy alkyl, alkyl, halogen, carboxyl or SO3H; R2 is -CH2COOZ, -CH(CH3)COOZ, Image , Image , or Image ; wherein R3 is -CH2COOZ, -CH(CH3)COOZ or a monovalent radical having the structure R-O-(CH2)m-?H-COOZ; X is a direct chemical bond, -O-, -S-, -NH-, -?-CH2COOZ or -?-CH(CH3)COOZ; n is the integer 2 or 3, with the proviso that when X represents a direct bond, n is 1, 2 or 3; Z is hydrogen or a unit of negative charge, and -(CH2)m- may also be -CH2-C(CH3)2-. The compounds are relatively simple, well tolerated, partially endowed with organ specificity and are suitable for application in nuclear spin tomography. The compounds may be - c - prepared by reacting inventive free polyamino-polycarboxylic acids having the formula Image (Ia) where R, R1, R2 and m have the same meaning as in formula I, or alkali metal, alkaline earth metal and/or amino salts of said acids, with salts, oxides, or hydroxides of iron(2+), iron(3+), gadolinium(3+), or manganese(2+), or with the basic salts of these metal ions. Imaging compositions and methods of use are also disclosed.

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