Novel cephalosporin compounds and process for preparing the same

• Main Authors: YOO, EUN JEONG, JANG, YONG JIN, LEE, CHANG SEOK, KIM, GEUN TAE, CHO, YANG RAE, JU, HYEONG RYEOL
• Format: Patent
• Language: English; Korean
• Published: 03.09.2003
• Edition: 7
• Subjects: CHEMISTRY; HETEROCYCLIC COMPOUNDS; METALLURGY; ORGANIC CHEMISTRY

PURPOSE: Provided are cephalosporin compounds and a preparation process thereof, which compounds have strong antimicrobial activity, especially to methicillin resistant Staphylococcus aureus(MRSA). CONSTITUTION: Cephalosporin compounds represented by the formula (1) are provided, wherein R1 and R2 are independently hydrogen, halogen, C1-6 alkyl, C1-6 alkylthio, aryl, arylthio or C5-6 heteroaryl containing 1 to 2 hetero atoms selected from nitrogen and oxygen; R3 is hydrogen or carboxy protecting group; R4, R5 and R6 are independently hydrogen, hydroxy, C1-6 alkyl, C1-6 alkyloxy or C1-6 alkylamino; R7 is hydrogen, hydroxy, amino, C1-6 alkyl, C1-6 alkyloxy, C1-6 alkylamino, or amino or hydroxy substituted or unsubstituted C1-6 alkylthio; Q is sulfur, oxygen or carbon; W and Y are independently C or N, provided that R4 and R6 are not present when W or Y is N; and olefin positioned at the C-3 site where heteroarylthio is substituted comprises cis or trans forms. A process for preparing the cephalosporin compounds of the formula (1) comprises the steps of: activating a compound of the formula (6) or salts thereof with an acylating agent; reacting the activated compound of the formula (6) with a compound of formula (5) to prepare a compound of the formula (11); and reducing the compound of the formula (11) from S to oxide, wherein p is 0 or 1; and a double bond positioned at the C-3 site comprises trans and cis forms. 본 발명은 하기 화학식 (1)의 신규 세팔로스포린 화합물, 그의 약제학적으로 허용되는 무독성염, 생리학적으로 가수분해 가능한 에스테르, 수화물, 용매화물 및 이들의 이성체, 이들을 함유하는 약제학적 조성물 및 그의 제조방법에 관한 것이다: 상기 식에서, R1, R2, R3, R4, R5, R6, R7, Q, W 및 Y 는 각각 명세서에 정의된 의미를 갖는다.