Isolation of N-Butylbenzenesulfonamide, Synthesis of Benzenesulfonamide Derivatives, and Use of N-Butylbenzenesulfonamide and Benzenesulfonamide Derivatives for Treating Benign Prostatic Hyperplasia and/or Prostate Carcinoma
AssigneeLTS Lohmann Therapie-Systeme AG
InventorsRudolf Matusch, Aria Baniahmad, Hans-Rainer Hoffmann
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Abstract
A process for isolating N-butylbenzenesulfonamide (NBBS) from biological material, the chemical synthesis of benzenesulfonamide derivatives, the use of NBBS and benzenesulfonamide derivatives for treating benign prostatic hyperplasia and/or prostate carcinomas the production of medicaments for the treatment thereof, and the use of NBBS and benzenesulfonamide derivatives as a lead substance in the development of active substances for treating benign prostatic hyperplasia and/or prostate carcinoma are provided.
Claims17
Use of a benzenesulfonamide derivative of the formula
- wherein R1 represents an aliphatic C1 to C12 hydrocarbon, R2 is selected from the group consisting of hydrogen and a completely or partially halogenated C1 residue, and R3 is selected from the group consisting of hydrogen and a nitro group, for producing a medicament for treating at least one of benign prostatic hyperplasia and prostate carcinoma.
Use of a benzenesulfonamide derivative of the formula
- wherein R1 represents an aliphatic C1 to C12 hydrocarbon, R2 is selected from the group consisting of hydrogen and a completely or partially halogenated C1 residue, and R3 is selected from the group consisting of hydrogen and a nitro group, for treating at least one of benign prostatic hyperplasia and prostate carcinoma.
Use of a benzenesulfonamide derivative of the formula
- wherein R1 represents an aliphatic C1 to C12 hydrocarbon, R2 is selected from the group consisting of hydrogen and a completely or partially halogenated C1 residue, and R3 is selected from the group consisting of hydrogen and a nitro group, as a lead substance for developing active substances for treating at least one of benign prostatic hyperplasia and prostate carcinoma.
A pharmaceutical preparation for treating at least one of benign prostatic hyperplasia and prostate carcinoma, wherein said preparation contains at least one benzenesulfonamide derivative of the formula
- wherein R1 represents an aliphatic C1 to C12 hydrocarbon, R2 is a completely or partially halogenated C1 residue and R3 is selected from the group consisting of hydrogen and a nitro group;
- or wherein R2 is selected from the group consisting of hydrogen and a completely or partially halogenated C1 residue and R3 is a nitro group.
A process for isolating N-butylbenzenesulfonamide from biological material, said process comprising the steps of:
- reducing the biological material to small pieces;
- extracting the biological material with a solvent to form an extract, said solvent being selected from the group consisting of univalent C1 to C4 alcohols and high-volatile, (partially) halogenated C1 hydrocarbons;
- fractionating the extract to form fractions containing N-butylbenzenesulfonamide;
- and
- isolating the N-butylbenzenesulfonamide from the fractions containing N-butylbenzenesulfonamide.
Benzenesulfonamide derivatives for treating at least one of benign prostatic hyperplasia and prostate carcinoma, of the formula
- wherein R1 represents an aliphatic C1 to C12 hydrocarbon, R2 is a completely or partially halogenated C1 residue and R3 is selected from the group consisting of hydrogen and a nitro group;
- or wherein R2 is selected from the group consisting of hydrogen and a completely or partially halogenated C1 residue and R3 is a nitro group.
A process for producing benzenesulfonamide derivatives of the formula
- wherein R1 represents an aliphatic C1 to C12 hydrocarbon, R2 is selected from the group consisting of hydrogen and a completely or partially halogenated C1 residue, and R3 is selected from the group consisting of hydrogen and a nitro group, comprising the steps of:
- converting a benzenesulfonic acid derivative of the formula
- with a primary aliphatic amine to form a reaction product;
- and
- shaking the reaction product is shaken out said reaction product with a solvent selected from the group consisting of dichloromethane and ethers wherein R1 represents halogen, R2 is selected from the group consisting of hydrogen and a completely or partially halogenated C1-residue:
- and R3 is selected from the group consisting of hydrogen and a nitro group.
Dependencies are inferred from the claim text.