RU97106553A - Iodinated x-ray contrast agents - Google Patents

Claims (14)

1. The compound of formula 1

where each of the C ₆ R ₅ fragments may be the same or different: each R represents a hydrogen atom or iodine or a M group, two or three non-adjacent R groups in each C ₆ R ₅ fragment are iodine atoms and one, two or three R groups in each of the C ₆ R ₅ fragments are M groups; each C ₆ R ₅ fragment represents a triiodophenyl group or a group in which each R is different from hydrogen; X represents a group, provided that a chain of 1, 2 or 3 atoms binds two C ₆ R ₅ fragments; and each M independently denotes a non-ionic hydrophilic fragment and its isomers.  2. The compound according to claim 1, wherein X denotes or contains a carbonyloxy group in the bridge chain.  3. The compound according to claim 1, wherein each of M represents a monohydroxy or polyhydroxy alkyl group. 4. The compound according to claim 1, wherein X denotes an asymmetric group, provided that a 2- or 3-atomic chain links two C ₆ R ₅ groups. 5. The compound according to claim 1, wherein the two C ₆ R ₅ groups are nonidentically substituted. 6. The compound according to claim 1, where at least one C ₆ R ₅ group has the formula 1

where the two R groups are the same or different. 7. The compound according to claim 1, where at least one C ₆ R ₅ group has the formula

or

where M groups are the same or different. 8. The compound according to claim 1, where the M groups denote linear or branched C _1-10 -alkyl groups in which one or more CH ₂ or CH groups are replaced by oxygen or nitrogen atoms, or which are substituted by one or more groups selected from oxo, hydroxy, amino, carboxyl derivative and oxo substituted sulfur and phosphorus.  9. The compound according to claim 1, wherein the M groups denote polyhydroxyl, hydroxyalkoxyalkyl or hydroxypolyalkoxyalkyl groups, optionally attached to the phenyl group via an amide bond. 10. The compound according to claim 1, where the M group is chosen from:
-CONH-CH ₂ CH ₂ OH
-CONH-CH ₂ CHOHCH ₂ OH
-CONH-CH (CH ₂ OH) ₂
-CON (CH ₂ CH ₂ OH) ₂
-CONH ₂
-CONHCH ₃
-OCOCH ₃
-N (COCH ₃ ) H
-N (COCH ₃ ) C _1-3 -alkyl,
—N (COCH ₃ ) -mono, bis or tris-hydroxy C _1-4 -alkyl,
-N (COCH ₂ OH) -mono, bis- or tris-hydroxy C _1-4 -alkyl,
C (COCH ₃ ) (mono, bis or tris-hydroxy C ₁ -C ₄ -alkyl) a,
-N (COCH ₂ OH) ₂
-CON (CH ₂ CHOHCH ₂ OH) (CH ₂ CH ₂ OH)
-CONH-C (CH ₂ OH) ₃ and
-CONH-CH (CH ₂ OH) (CHOHCH ₂ OH). 11. The compound according to claim 1, where M groups denote polyhydroxy-C _1-4 -alkyl groups. 12. The compound according to claim 1, where X denotes an oxygen atom or a group NR ¹ , CO, SO ₂ , CR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ COCO, CONR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ , COCR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ SOCR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ , SO ₂ NR ¹ , CR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ CR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ CR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ O, NR ¹ CONR ¹ , OCONR ¹ , CR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ NR ¹ , CONR ¹ CO, -CONR ¹ CR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ , OCOO, CR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ OCR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ OCR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ CO, CR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ CONR ¹ , CR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ CR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ CR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ COCH ¹ R ¹ CO, CR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ NR ¹ CR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ CR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ SO ₂ NR ¹ , CR $\genfrac{}{}{0ex}{}{\text{one}}{\text{2}}$ OCO, NR ¹ SO ₂ NR ¹ , where R ¹ is hydrogen or a C _1-6 alkyl or alkoxy group, optionally substituted by hydroxy, alkoxy, oxa or oxo, or where R ¹ may be a hydroxyl group. 13. The compound according to claim 1 of one of the formulas

where M is - as defined in claim 1 and R ¹ - as defined in item 12.  14. A diagnostic composition comprising a compound of formula 1, as defined in any of the preceding claims, with at least one physiologically acceptable carrier or excipient.