Claims
- 1. A tetraazacyclododecane compound of the formula I ##STR7## in which E stands for radical --CH(R.sup.1)--CO.sub.2 Y with each Y independently meaning a hydrogen atom or a metal ion equivalent of an element of atomic numbers 21-29, 31, 32, 37-39, 42-44, 47, 49 or 57-83 and R.sup.1 meaning a hydrogen atom, a branched or unbranched C.sub.1 -C.sub.30 alkyl, C.sub.6 -C.sub.10 aryl or C.sub.7 -C.sub.30 aralkyl group, each optionally substituted with 1 to 6 hydroxy groups,
- Q stands for a radical --CH(R')--CH(OH)R
- with R meaning a branched or unbranched C.sub.1 -C.sub.9 saturated carbon chain or C.sub.1 -C.sub.6 saturated carbon chain containing at least one aryl radical, each carbon chain containing 1 to 10 oxa atoms and
- optionally substituted by 1 to 6 hydroxy or --OCOR.sup.2 groups,
- with R.sup.2 meaning a hydrogen atom or a branched or unbranched C.sub.1 -C.sub.9 alkyl, C.sub.6 -C.sub.10 aryl or C.sub.7 -C.sub.30 aralkyl radical,
- wherein R optionally is substituted by 1 to 2 --CO.sub.2 R.sub.2, 1 to 2 --OCO-- groups, 1 to 2 cyclohexane and/or cyclohexylene radicals, each of which can be substituted by 1 to 3 (CH.sub.2).sub.k COOR.sup.2 groups with k meaning the numbers 0 to 10, 1 to 5 C.sub.1 -C.sub.7 alkoxy, C.sub.6 -C.sub.10 aryloxy or C.sub.7 -C.sub.10 aralkyloxy groups, and/or a radical --NR.sup.2 --COR.sup.3 or --CONR.sup.2 R.sup.3, wherein R.sup.3 has one of the meanings indicated for R.sup.2, and wherein the aryl radicals optionally contained in the chain can be substituted by 1 to 3 branched or unbranched C.sub.1 -C.sub.30 -alkyl, C.sub.6 -C.sub.10 -aryl or C.sub.7 -C.sub.30 -aralkyl radicals, each alkyl chain optionally substituted by 1 to 5 oxa atoms and each alkyl chain or aryl ring optionally substituted by 1 to 3 hydroxy radicals, 1 to 5 C.sub.1 -C.sub.7 alkoxy groups and/or 1 to 3 (CH.sub.2).sub.k COOR.sup.2 groups, and/or by 1 to 3 F, Cl, Br, OH, NO.sub.2, NH.sub.2, NCS, CO.sub.2 R.sup.2, NHCOCH.sub.2 Cl, NHCOCH.sub.2 Br, NHCOCH.sub.2 R.sup.2, or CON.sub.3 radicals, and
- R' meaning a hydrogen atom or an R group, in which, if R' stands for a hydrogen atom, in the case of 2-oxa-C.sub.1 -C.sub.30 alkyl chain, the latter, in addition to an optionally present, terminal methoxy or ethoxy group, has to be substituted by at least one of the above-identified radicals,
- or a salt thereof with an inorganic and/or organic base, amino acid or amino acid amide;
- provided that R does not terminate in a linear alkoxy group.
- 2. The compound of claim 1, wherein each R.sup.1 stands for a hydrogen atom.
- 3. The compound of claim 1, wherein, in the compound of Formula I, R is --CH.sub.2 --O--C.sub.6 H.sub.5, --CH.sub.2 --O--CH.sub.2 C.sub.6 H.sub.5, --CH.sub.2 --O--C.sub.10 H.sub.20 --OH, --CH.sub.2 --O--C.sub.10 H.sub.20 --COOH, --CH.sub.2 --O--C.sub.5 H.sub.10 --COOH, --CH.sub.2 --CH.sub.2 --CH.sub.2 --CH.sub.2 --O--CH.sub.2 --COOH, --CH.sub.2 --O--C.sub.6 H.sub.10 --CO.sub.2 H, --CH.sub.2 --O--C.sub.6 H.sub.10 --OH, --C.sub.6 H.sub.10 --O--CH.sub.2 --COOH, --CH.sub.2 --O--C.sub.5 H.sub.10 NHCOC.sub.6 H.sub.5, --CH.sub.2 --O--C.sub.2 H.sub.5 NHCOC.sub.6 H.sub.5, --CH.sub.2 --O--C.sub.2 H.sub.5 CONH--C.sub.3 H.sub.7, --CH.sub.2 --O--CH.sub.2 --CH(OH)CH.sub.2 OH, --CH.sub.2 --O--C.sub.6 H.sub.4 NCS, --CH.sub.2 --O--C.sub.6 H.sub.4 --COOH, --CH.sub.2 O--C.sub.6 H.sub.4 --C.sub.5 H.sub.10, --OH, --CH.sub.2 --O--C.sub.6 H.sub.3 (CH.sub.3).sub.2, --CH.sub.2 --O--C.sub.6 H.sub.4 (CH.sub.2).sub.2 --COOH, --CH.sub.2 --O--C.sub.6 H.sub.4 --OCH.sub.2 COOH,--CH.sub.2 --O--C.sub.6 H.sub.4 COOH, --CH.sub.2 O--CH.sub.2 --C.sub.6 H.sub.4 COOH, --CH.sub.2 O--C.sub.6 H.sub.4 CH .sub.2 COOH, --CH.sub.2 O--C.sub.6 H.sub.4 CH.sub.2 COOC.sub.2 H.sub.5, --(CH.sub.2).sub.9 --O--CH.sub.2 --C.sub.6 H.sub.5, --CH.sub.2 --OCO--C.sub.15 H.sub.31, --CH.sub.2 --O--C.sub.9 H.sub.18 --O--CH.sub.2 C.sub.6 H.sub.5, --CH.sub.2 --O--C.sub.9 H.sub.18 OH, --C.sub.8 H.sub.16 --(CH.sub.2 --O--CH.sub.2 --C.sub.6 H.sub.5)--C.sub.2 H.sub.5, --C.sub.9 H.sub.18 --O--C.sub.6 H.sub.4 --O--CH.sub.2 --C.sub.6 H.sub.5, --C.sub.9 H.sub.18 --O--C.sub.6 H.sub.4 --OH, --(CH.sub.2).sub.9 --O--CH.sub.2 --C.sub.6 H.sub.4 --CH.sub.2 COOH, --(CH.sub.2).sub.9 --O--C.sub.10 H.sub.20 --OH, --(CH.sub.2).sub.9 --O--C.sub.5 H.sub.10 --COOH, --(CH.sub.2).sub.9 --OCOCH.sub.3, --(CH.sub.2).sub.9 --OCOC.sub.4 H.sub.9 --(CH.sub.2) .sub.9, --OCOC.sub.2 H.sub.4 COOH, --(CH.sub.2).sub.9 --OCOC.sub.6 H.sub.4 COOH or --(CH.sub.2).sub.9 --OCOC.sub.6 H.sub.10 COOH.
- 4. A compound according to claim 1, wherein each Y stands for a hydrogen atom.
- 5. A compound according to claim 1, wherein at least two of the substituents Y are metal ion equivalents of at least one element of atomic numbers 21-29, 42, 44 or 57-83 or at least one radionuclide of an element of atomic numbers 21, 26, 27, 29, 31, 32, 37-39, 43, 47, 49, 62-64, 67, 70, 71, 75, 77, 79 and 83.
- 6. A compound according to claim 1, wherein R' stands for a hydrogen atom.
- 7. A pharmaceutical composition comprising a physiologically compatible compound according to claim 1 and a pharmaceutical carrier.
- 8. The compound of claim 1, wherein R contains at least one aryl radical substituted with at least one NO.sub.2, NH.sub.2, NCS, NHCOCH.sub.2 Cl, NHCOCH.sub.2 Br, NHCOCH.sub.2 R.sup.2, or CON.sub.3 radical substituent.
- 9. The compound of claim 1, wherein Q is 3-(4-nitrophenoxy)-2-hydroxypropyl.
- 10. The compound of claim 1, wherein Q is 2,6,7-trihydroxy-4-oxaheptyl.
- 11. The compound of claim 1, wherein at least two Y substituents are metal ion equivalents of an element of atomic number 21-29, 42, 44 or 58-70.
- 12. The compound of claim 1, wherein Q is 3-(4-aminophenoxy)-2-hydroxypropyl.
- 13. The compound of claim 1, wherein Q is 3-(4-isothiocyanatophenoxy)-2-hydroxypropyl.
- 14. The compound of claim 1, wherein Q is 3-(4-carboxyphenoxy)-2-hydroxypropyl.
Priority Claims (1)
Number |
Date |
Country |
Kind |
40 35 760.0 |
Nov 1990 |
DEX |
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Parent Case Info
This is a Continuation of Ser. No. 07/789,178 filed Nov. 8, 1991, now U.S. Pat. No. 5,277,895 Jan. 11, 1994.
US Referenced Citations (10)
Foreign Referenced Citations (7)
Number |
Date |
Country |
232751 |
Aug 1987 |
EPX |
299795 |
Jan 1989 |
EPX |
305320 |
Mar 1989 |
EPX |
365412 |
Apr 1990 |
EPX |
434345 |
Jun 1991 |
EPX |
434346 |
Jun 1991 |
EPX |
3625417 |
Feb 1988 |
DEX |
Non-Patent Literature Citations (1)
Entry |
Place et al., 5th Soc. Magnetic Resonance in Med. Mtg., Montreal, Canada, Aug. 1986. |
Continuations (1)
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Number |
Date |
Country |
Parent |
789178 |
Nov 1991 |
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