While Kichitaro entered the manufacturing field, he also aggressively expanded the trade area for the wholesale sector. In the second decade of the Showa period, Kobayashi's wholesale business expanded into the three fingers of west Japan. It should especially be noted that the company planned its entry into Tokyo at this time.

Metropolitan Tokyo is Japan's major consuming region, and a company must move into Tokyo at some point in order to establish a foothold in Kanto and Tohoku. However, there are major cultural differences in commercial practices between Osaka and Tokyo, to the extent that many in Doshomachi believed there was a jinx pre-determining that a company trying to establish itself in Tokyo would inevitably fail.

In 1939, Kichitaro sent an employee named Terajima to Tokyo to establish a base. Terajima took the products that sold well in Kansai and set off for Tokyo in high spirits, but unfortunately this move was premature. Although he was actively assisted by Fujii, the president of Ryukakusan, he left Tokyo after one year.

Although this first attempt to secure a foothold in Tokyo did not succeed, it was extremely helpful when Tokyo Kobayashi Daiyakubo was established after World War II.

Again, it was President Saburo that succeeded to President Kichitaro's strategy.

However, the company rode the trends of the times and extended its sales channels into Taiwan, Korea and parts of China. Japan had a strong influence in all of these areas, demand for Japan's pharmaceutical products was significant and employees were regularly dispatched here, and in 1941 employees were sent to new posts in Beijing.

The office in Beijing was in charge of China's northern region. As long as they had products to market, they would sell. However, the fires of war intensified, and since Japan had already lots its naval supremacy and air superiority, the employees stationed there were called to military duty before they had had sufficient chance to act. Sales activities were discontinued and everything was lost when the war ended.

Small amounts of products were shipped to South-east Asia and America, but most of these were sold to Japanese living overseas.