EP0064040A1
Expired / Lapsed
EP
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Therapeutically active disulphide compounds and their use
Assignee: Pfizer Health AB
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Filing: 1982-04-05
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Granted: —
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Expires: 2002-04-05
Abstract
Abstract Therapeutically active organic compound exhibiting at least one group comprising a structure -S'-S"-R, wherein the group -S"-R is defined by R being an organic group comprised in a physiologically acceptable compound H-S"-R obtainable by the splitting of the disulfide bridge -S'-S"- in said structure, in which compound H-S"-R the sulfur atom S" is bound to a carbon atom in a heterocyclic aromatic ring in R having a configuration being such that the compound H-S"-R, while maintaining physiological acceptability, is stabilized, by tautomerism or resonance involving the sulfur atom S" bound to R, so as to be mainly excluded from reaction involving thiol disulfide exchange; S' being bound to an aliphatic carbon atom; and said compound, in addition to the group or groups comprising the structure -S'-S"-R, consisting of a residue of a therapeutically active organic base compound of non-poly-peptide structure bound to S'. The invention also relates to a method of modifying a therapeutically active organic compound of non-polypeptide structure by introducing a structure -S'-S"-R according to above; a method of treating diseases by administration of a compound according to the invention and also to a pharmaceutical composition containing at least one compound according to the invention.
Inventors
- 👤 Jan Per Erik Carlsson
- 👤 Rolf Erik Axel Verner Axen
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-10-24 01:21
CPC Classifications
C; C07; C07D; C07D213/00; C07D213/02; C07D213/04; C07D213/60; C07D213/62; C07D213/70; C07D213/71; C07D213/89; C07D277/00; C07D277/60; C07D277/62; C07D277/68; C07D277/70; C07D277/76; C07D277/78; C07D499/00; C07H; C07H15/00; C07H15/20; C07H15/24; C07H15/252
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
144 words
Therapeutically active organic compound, which exhibits at least one group comprising the structure -S'-S"-R, wherein the group -S"-R is defined by R being an organic group comprised in a physiologically acceptable compound H-S''-R obtainable by the splitting of the disulfide bridge -S'-S''- in said structure, in which compound H-S''-R the sulfur atom S'' is bound to a carbon atom in a heterocyclic aromatic ring in R, having a configuration being such that the compound H-S''-R, while maintaining physiological acceptability, is stabilized, by tautomerism or resonance involving the sulfur atom S'' bound to R, so as to be mainly excluded from reaction involving thiol disulfide exchange; S' being bound to an aliphatic carbon atom; and said compound, in addition to the group or groups comprising the structure -S'-S"-R, consisting of a residue of a therapeutically active organic base compound of non-polypeptide structure bound to S'.
Claim 2
Dependent Claim
144 words
Therapeutically active organic compound, which exhibits at least one group comprising the structure -S'-S"-R, wherein the group -S"-R is defined by R being an organic group comprised in a physiologically acceptable compound H-S''-R obtainable by the splitting of the disulfide bridge -S'-S''- in said structure, in which compound H-S''-R the sulfur atom S'' is bound to a carbon atom in a heterocyclic aromatic ring in R, having a configuration being such that the compound H-S''-R, while maintaining physiological acceptability, is stabilized, by tautomerism or resonance involving the sulfur atom S'' bound to R, so as to be mainly excluded from reaction involving thiol disulfide exchange; S' being bound to an aliphatic carbon atom; and said compound, in addition to the group or groups comprising the structure -S'-S"-R, consisting of a residue of a therapeutically active organic base compound of non-polypeptide structure bound to S'.
Claim 3
Dependent Claim
195 words
Therapeutically active organic compound according to claim 1, wherein the therapeutically active compound consist of the formula T 1 -X-A-S'-S"-R, where a) R, S" and S' have the above given meaning b) A is a straight, branched or cyclic hydrocarbon chain of 1 - 10 carbon atoms, which optionally is substituted with 1 - 3 hydroxyl groups and which optionally is broken by 1 - 3 oxygen or sulfur atoms, preferably at most one atom other than carbon and hydrogen is bound to one and the same carbon atom in A c) X is 1) a direct link to an amino- or amide- nitrogen atom or carbon atom in T 1 2) the group -CO- bound to a nitrogen or oxygen atom in T 1 3) the group -CO-0- bound to a carbon or nitrogen atom in T 1 4) the atom -0- bound to a carbon atom in T 1 and d) T1 is a residue of a preferably therapeutically active organic compound of non-polypeptide structure of the formula T = i) T 1 -X-H ii) T 1 -X-A-H or iii) T 1 -X-A-S'-H where X, A and S' have the above given meaning.
Claim 4
Dependent Claim
20 words
Therapeutically active organic compound according to claim 2, wherein the therapeutically active compound T being a cytostatic or antimicrobial substance.
Claim 5
Dependent Claim
27 words
Therapeutically active compound according to claim 3, wherein the therapeutically active compound T being melfalan, an antracyclineglycoside, a penicillin, a cephalosporin, a tetracycline or a sulfa compound.
Claim 6
Dependent Claim
35 words
Therapeutically active compound according to any of the claims 1 - 4, wherein R in the structure -S'-S''-R being 2-benzothiazolyl, 2-pyridyl, 5-nitro-2-pyridyl, 4-pyridyl, 5-carboxy-2-pyridyl or the N-oxide of any of the last mentioned four groups.
Claim 7
Dependent Claim
136 words
Method of modifying a therapeutically active organic compound of non-polypeptide structure, wherein an atom or group, which is exchangeable while maintaining therapeutical activity,is replaced, by methods known per se, with a group comprising a structure -S'-S''-R, where -S''-R is defined by R being an organic group comprised in a physiologically acceptable compound H-S''-R obtainable by the splitting of the disulfide bridge -S'-S''- in said structure, in which compound H-S''-R the sulfur atom S'' is bound to a carbon atom in a heterocyclic aromatic ring in R, having a configuration being such that the compound H-S''-R, while maintaining physiological acceptability, is stabilized, by tautomerism or resonance involving the sulfur atom S'' bound to R, so as to be mainly excluded from further reaction involving thiol disulfide exchange, and where S' being bound to an aliphatic carbon atom.
Claim 8
Dependent Claim
136 words
Method of modifying a therapeutically active organic compound of non-polypeptide structure, wherein an atom or group, which is exchangeable while maintaining therapeutical activity,is replaced, by methods known per se, with a group comprising a structure -S'-S''-R, where -S''-R is defined by R being an organic group comprised in a physiologically acceptable compound H-S''-R obtainable by the splitting of the disulfide bridge -S'-S''- in said structure, in which compound H-S''-R the sulfur atom S'' is bound to a carbon atom in a heterocyclic aromatic ring in R, having a configuration being such that the compound H-S''-R, while maintaining physiological acceptability, is stabilized, by tautomerism or resonance involving the sulfur atom S'' bound to R, so as to be mainly excluded from further reaction involving thiol disulfide exchange, and where S' being bound to an aliphatic carbon atom.
Claim 9
Dependent Claim
163 words
Method of treating diseases of mammals, including humans, wherein a therapeutically effective amount of a therapeutically active compound of non-poly- peptide structure exhibiting at least one group comprising a structure -S'-S''-R, is administered to the mammals, where -S"-R is defined by R being an organic group comprised in a physiologically acceptable compound H-S''-R obtainable by the splitting of the disulfide bridge of said structure, in which compound H-S''-R the sulfur atom S" is bound to a carbon atom in a heterocyclic aromatic in R, having a configuration being such that the compound H-S''-R, while maintaining physiological acceptability, is stabilized, by tautomerism or resonance involving the sulfur atom S'' bound to R, so as to be mainly excluded from further reaction involving thiol disulfide exchange; S' being bound to an aliphatic carbon atom; and said compound, in addition to the group or groups.comprising the structure -S'-S''-R, also consisting of a residue of a therapeutically active organic base compound of non-polypeptide structure bound to S'.
Claim 10
Dependent Claim
163 words
Method of treating diseases of mammals, including humans, wherein a therapeutically effective amount of a therapeutically active compound of non-poly- peptide structure exhibiting at least one group comprising a structure -S'-S''-R, is administered to the mammals, where -S"-R is defined by R being an organic group comprised in a physiologically acceptable compound H-S''-R obtainable by the splitting of the disulfide bridge of said structure, in which compound H-S''-R the sulfur atom S" is bound to a carbon atom in a heterocyclic aromatic in R, having a configuration being such that the compound H-S''-R, while maintaining physiological acceptability, is stabilized, by tautomerism or resonance involving the sulfur atom S'' bound to R, so as to be mainly excluded from further reaction involving thiol disulfide exchange; S' being bound to an aliphatic carbon atom; and said compound, in addition to the group or groups.comprising the structure -S'-S''-R, also consisting of a residue of a therapeutically active organic base compound of non-polypeptide structure bound to S'.
Claim 11
Dependent Claim
22 words
Pharmaceutical composition, containing as an active substance at least one therapeutically active compound according to any of the claims 1 - 6.
References Cited (Backward Citations)
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