1-Benzenesulfonyl pyrrolidine derivatives as bradykinin receptor antagonists
AssigneeFournier Industrie et Sante
InventorsPierre Dodey, Michel Bondoux, Patrick Houziaux, Martine Barth, Khan Ou
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Abstract
This invention relates to compounds of the formula where X is halogen, R1 is H or a C1-C3 alkyl, R2 is H or OH and R3 is one of in which A is a single bond or a —CO(CH2)p—NH— group, R4 is H or —C(═NR5)NHR′5, R5 and R′5 are each H or a C1-C6 alkyl group, R6 is H or a C1-C3 alkyl group, m is 0, 1 or 2; n is 2, 3 or 4; p is 1, 2 or 3; plus their acid addition salts. The invention likewise relates to the method for their preparation and their therapeutic applications.
Claims7
An N-Benzenesulfonylpyrrolidine compound, which is selected from the group consisting of
- (i) compounds of the formula
- in which:
- X is a halogen atom,
- R1 is a hydrogen atom or a C1-C3 alkyl group having a linear or branched hydrocarbon chain,
- R2 is a hydrogen atom or an OH group, and
- R3 is a group
- in which:
- A is a single bond or a group —CO—(CH2)p—NH—,
- R4 is a hydrogen atom or a group
- R5 and R′5, which are identical or different, are each a hydrogen atom or a linear, branched or cyclized C1-C6 alkyl group,
- R6 is a hydrogen atom or a linear or branched C1-C3 alkyl group,
- m is an integer having a value of 0, 1 or 2,
- n is an integer having a value of 2, 3 or 4, and
- p is an integer having a value of 1, 2 or 3;
- and
- (ii) their addition salts.
An intermediate compound useful for the preparation of the compounds of formula I which is represented by the formula
- in which:
- R1 is CH3,
- R2 is H or OH, and
- R3 is OH or OCH3.
Dependencies are inferred from the claim text.