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In advanced countries, the total number of elderly recipients who take medicine every day has been increasing due to the aging populations. Since the recipients have many risks of inappropriate medication (e.g. overdose), we propose and develop an intelligent medicine case (iMec) and a medication support system (iMec System) in order to assist an elderly recipient in taking medicine adequately and help his/her caregivers with monitoring. There are 3 challenging problems to realize the iMec-centered system, so we introduce them in this paper. The first one is how to recognize medicine in the medicine case in order that the system can check the adequacy of dosage. The second one is how to estimate the recipient's present behavioral condition in order that the system can check the adequacy of usage (i.e. dosing timing). By using the results of medicine recognition and condition estimation, the iMec System could detect some signs of incorrect medication based on If-Then rules. The last challenging problem is how to help the elderly recipient to take medicine in order to keep the recipient's medication compliance well. These problem were essentially solved, however, it remains a few difficult and important problem.