using System; using System.Collections.Generic; using System.IO; using System.Linq; using System.Text.RegularExpressions; public class Test { public static void Main() { var text = "Artículo 1. This is a test that includes : 1) Sample text 2) Sample text"; var result = Regex.Split(text, @"(?!^)\s+(?=\bArtículo\s+[0-9]+\.|[a-z]\)|[1-9]\d?\)|\bPárrafo\b)", RegexOptions.None); Console.WriteLine(string.Join("\n", result)); } }