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US 5,686,492 AGranted
Disubstituted p-fluorobenzenesulfonamides
AssigneeSchering Corporation
InventorsUlrich Niedballa, Johannes Platzek, Bernd Raduchel
Life of this patent
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Abstract
Described herein are disubstituted p-fluorobenzenesulfonamides, containing a CF.sub.3 group, of general formula I ##STR1## which are suitable as NMR diagnostic agents.
Claims13
A disubstituted p-fluorobenzene sulfonamide of the formula I ##STR12## in which Z stands for a CF.sub.3 group or a hydrogen atom,
- Y stands for a (CH.sub.2).sub.o CONR.sup.1 R.sup.2 group with o meaning 1 and R.sup.1 and R.sup.2, independently of one another, meaning hydrogen or a C.sub.1 -C.sub.6 alkyl group optionally substituted by 1 to 4 hydroxy groups,
- X stands for a hydrogen atom or for one of the meanings indicated for Y,
- W stands for a C.sub.0 -C.sub.6 alkylene group, optionally substituted by 1 to 4 hydroxy groups or interrupted by 1 to 2 oxygen atoms, where C.sub.0 is a direct bond,
- n stands for numbers 0 or 1,
- A stands for radicals --OH, OR.sup.3, --CF.sub.3, --CH.sub.2 CF.sub.3, --NH--CR.sup.3 (CF.sub.3)--COOH or --NHCH.sub.2 COOH with R.sup.3 meaning a hydrogen atom or a straight-chain or branched-chain C.sub.1 -C.sub.6 alkyl group optionally substituted by 1 to 2 hydroxy group(s),
- provided that X stands for a hydrogen atom if Z means a CF.sub.3 group, that X has one of the meanings indicated for Y, if Z stands for a hydrogen atom, that A is CF.sub.3, or --NH--CR.sup.3 (CF.sub.3)--COOH when Z is hydrogen, and that optionally the acid groups present in the molecule are present in the form of their amides or in the form of salts with organic or inorganic bases.
3 more elements
A process for the production of a disubstituted p-fluorobenzenesulfonamide of formula I ##STR15## in which Z stands for a CF.sub.3 group or a hydrogen atom,
- Y stands for a (CH.sub.2).sub.o CONR.sup.1 R.sup.2 group with o meaning 1 and R.sup.1 and R.sup.2, independently of one another, meaning hydrogen or a C.sub.6 -C.sub.6 alkyl group optionally substituted by 1 to 4 hydroxy groups,
- X stands for a hydrogen atom or for one of the meanings indicated for Y,
- W stands for a C.sub.0 -C.sub.6 alkylene group, optionally substituted by 1 to 4 hydroxy groups or interrupted by 1 to 2 oxygen atoms, where C.sub.0 is a direct bond,
- n stands for numbers 0 or 1,
- A stands for radicals --OH, OR.sup.3, --CF.sub.3, --NH--CR.sup.3 (CF.sub.3)--COOH or --NHCH.sub.2 COOH with R.sup.3 meaning a hydrogen atom or a straight-chain or branched-chain C.sub.1 -C.sub.6 alkyl group optionally substituted by 1 to 2 hydroxy group(s),
- provided that X stands for a hydrogen atom if Z means a CF.sub.3 group, that X has one of the meanings indicated for Y, if Z stands for a hydrogen atom, that A is CF.sub.3, or --NH--CR.sup.3 (CF.sub.3)--COOH when Z is hydrogen, and that optionally the acid groups present in the molecule are present in the form of their amides or in the form of salts with organic or inorganic bases,
- which comprises reacting a compound of formula II ##STR16## in which Y and X have the above-indicated meaning, and the hydroxy and carbonyl groups optionally contained in them optionally are present in protected form, with a compound of formula III
- CISO.sub.2 (W--CO).sub.n --A (III),
- in which
- W, n and A have the above-indicated meaning, and the hydroxy and carboxy groups optionally contained in A optionally are present in protected form,
- removing the optionally present protective groups, and if desired, converting the acid groups optionally present in the molecule with organic or inorganic bases to the corresponding salts or,
- optionally after activation of the acid groups, by reaction with an amine to the corresponding amides.
9 more elements
Dependencies are inferred from the claim text.