US 7,022,846 B2 · Metabolites of prinomastat and their synthesis

Abstract

Metabolites of a matrix metalloproteinase inhibitor prinomastat and their synthesis. These metabolites are: (3S)-N-hydroxy-4-(4-((1-oxy-pyrid-4-yl)oxy)benzenesulfonyl)-2,2-dimethyl-tetrahydro-2H-1,4-thiazine-3-carboxamide (M6); (3S)-2,2-dimethyl-1,1-dioxo-4-[4-(1-oxy-pyridin-4-yloxy)-benzenesulfonyl]-thiomorpholine-3-carboxylic acid amide (M7); (3S)-2,2-dimethyl-4-[4-(1-oxypyridin-4-yloxy)-benzenesulfonyl]-thiomorpholine-3-carboxylic acid amide (M8); (3S)-2,2-dimethyl-1,1-dioxo-4-[4-(pyridin-4-yloxy)-benzenesulfonyl]-thiomorpholine-3-carboxylic acid amide (M2); and (3S)-2,2-dimethyl-4-[4-(pyridin-4yloxy)-benzenesulfonyl)-thiomorphpline-3-carboxylic acid amide (M3).

Claims26

Dependent claims

A process for synthesizing a compound of formula 11, N-hydroxy-4-(4-((1-oxy-pyrid-4-yl)oxy)benzenesulfonyl)-2,2-dimethyl-tetrahydro-2H-1,4-thiazine-3-carboxamide, comprising the steps of:

(i) protecting a compound of formula 1
with a protecting group, P1, to form a compound of formula 2
(ii) activating the compound of formula 2 with an activating agent, A1, to form a compound of formula 3
(iii) coupling the compound of formula 3 with a compound of formula 4 having an ester, E1
to form a compound of formula 5
(v) removing the protecting group, P1, from the compound of formula 5 to form a compound of formula 6
(vi) coupling the compound of formula 6 with p-nitro pyridine N-oxide, a compound of formula 7
to form a compound of formula 8
(vii) removing the ester, E1, from the compound of formula 8 to form a compound of formula 9
(vii) activating the compound of formula 9 with an activating agent, A2, to form a compound of formula 10
(viii) treating the compound of formula 10 with hydroxylamine to form the compound of formula 11

8 more elements

Dependencies are inferred from the claim text.

Metabolites of prinomastat and their synthesis

Life of this patent

Metabolites of prinomastat and their synthesis

Life of this patent

Abstract

Claims26