In recent years, 5-axis controlled machine tools attract attention because of the increase in demand for improvements in productivity. Ball end mill is easy to control its location against a cutting surface, and is often used for the 5-axis controlled machining. However, the cutting removal rate of ball end mill is insufficient. Square and radius end mills has the higher removal rate more than ball end mill. On the other hand, the 5-axis controlled machining with square or radius end mill may be difficult compared with the case of ball end mill. In this report, 2-dimensional configuration space that expresses one tool posture by one point on the space was extended to cope with the machining with square and radius end mills. Furthermore, the new tool path generation method was proposed, which can reduce the cutting remains near a character line. As the result of machining simulations, the cutting remains near a character line were reduced, and the utility of the proposed tool path generation method was actually confirmed.