Hello, Chest pain in a patient with diabetes always raises questions about coronary heart disease. In diabetics a heart attack may present with atypical symptoms, so investigation is required in almost all cases. Your case sounds a little baffling. Improvement with antacids strongly suggests a gastrointestinal disorder (esophagitis, peptic ulcer, reflux, etc). Recurrence with eating also suggests a gastrointestinal disorder. Pain of the left side of the chest is not common for gastrointestinal disorders. In such cases the pain is usually central (behind the sternum) or epigastric (upper abdominal). What applies to heart attack symptoms though, may apply to other types of symptoms as well so a gastrointestinal disorder may indeed present with atypical symptoms in diabetics. Since you do have some serious risk factors (hypertension, diabetes, high cholesterol) you d better do at least an electrocardiogram and cardiological consultation. If everything seems to be OK then using either an antacid or acid-reducing drugs like ranitidine or omeprazole would sound like a good idea. For persistent complaints, an upper gastrointestinal endoscopy might be required. Hope I have answered your query. Let me know if I can assist you further.