Reference

Synthesis of 7-amino-3-(propen-1-y1)-4-cephalosporanic acid

All Rights Reserved. Synthesis of 7-amino-3-(propen-1-y1)-4-cephalosporanic acid. Chu, Xiuhai (Shanghai Medical & Pharmaceutical Technology Development Co., Ltd., Shanghai 201203, Peop. Rep. China). Shanghai Yiyao, 26(2), 84-85 (Chinese) 2005 Shanghai Yiyao Zazhishe. CODEN: SYHIBK. 104146-10-3 and 120709-09-3 which are cas registry numbers of chemicals are mentioned. ISSN: 1006-1533. DOCUMENT TYPE: Journal CA Section: 26 (Biomolecules and Their Synthetic Analogs) Section cross-reference(s): 28 The synthesis of 7-amino-3-(propen-1-y1)-4-cephalosporanic acid from 7-[2-phenylacetyl]amino-3-chloromethyl-4-cephalosporanic acid 4-methoxybenzyl ester was reported. The overall yield could reach to 60%. .

Process for selective preparation of Z-isomer of cefditoren and pharmaceutically acceptable salts and esters thereof

Process for selective preparation of Z-isomer of cefditoren and pharmaceutically acceptable salts and esters thereof. Prasad, Mohan; Kumar, Yatendra; Singh, Kaptan; Prasad, Ashok; Richhariya, Santosh (Ranbaxy Laboratories Limited, India). PCT Int. Appl. WO 2005016936 A2 24 Feb 2005, 29 pp. DESIGNATED STATES: W: AE, AG, AL, AM, AT, AU, AZ, BA, BB, BG, BR, BW, BY, BZ, CA, CH, CN, CO, CR, CU, CZ, DE, DK, DM, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, HR, HU, ID, IL, IN, IS, JP, KE, KG, KP, KR, KZ, LC, LK, LR, LS, LT, LU, LV, MA, MD, MG, MK, MN, MW, MX, MZ, NA, NI, NO, NZ, OM, PG, PH, PL, PT, RO, RU, SC, SD, SE, SG, SK, SL, SY, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, YU, ZA, ZM, ZW; RW: AT, BE, BF, BJ, CF, CG, CH, CI, CM, CY, DE, DK, ES, FI, FR, GA, GB, GR, IE, IT, LU, MC, ML, MR, NE, NL, PT, SE, SN, TD, TG, TR. (English). (World Intellectual Property Organization). CODEN: PIXXD2. CLASS: ICM: C07D501-00. ICS: A61K031-545. APPLICATION: WO 2004-IB2648 13 Aug 2004. PRIORITY: IN 2003-DE1004 14 Aug 2003. DOCUMENT TYPE: Patent CA Section: 26 (Biomolecules and Their Synthetic Analogs) Section cross-reference(s): 1, 63 The present invention relates to a selective process for prepn. of Z-isomer I of cefditoren and pharmaceutically acceptable salts and esters thereof. cefditoren possesses a wide spectrum of antibacterial activity against Gram-pos. and Gram-neg. bacteria (no data). The process comprises: (a) reacting 7-ATCA (II) with iminoacetate III [Z = Z1, Z2, OP(OR)(OR1), SP(OR)(OR1); Rc = CPh3, Ac, CHPh2, acetamidophenyl; R = (un)branched C1-7-alkyl, alkenyl, alkynyl, C6-10-aryl, aralkyl; R1 = (un)branched C1-6-alkyl, cycloalkyl, aryl, aralkyl, heterocyclyl]; (b) isolating cefditoren, or a pharmaceutically acceptable salt thereof, from the reaction mass; (c) optionally converting cefditoren , or a pharmaceutically acceptable salt thereof, to a pharmaceutically acceptable ester via reaction with Me3CCO2CH2X [X = halogen (I, Cl, Br)]; with the proviso II contains less then 2% E-isomer. Thus, cefditoren pivoxil was prepd. from 4-methoxybenzyl 3-(chloromethyl)-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2. 104146-10-3 is also in the experiment. 0]oct-2-ene-2-carboxylate via sequential reaction with PPh3 in aq. CHCl3 contg. NaI, hydrohalide elimination with aq. NaOH, Wittig coupling with 4-methylthiazole-5-carboxaldehyde in PrOH, deacylation with penicillin G amidase in H2O, and reacylation of 7-ATCA (II) with S-(1,3-Benzothiazol-2-yl) (2-amino-1,3-thiazol-4-y)[(Z)-methoxyimino]ethanethioate in aq. THF contg. Et3N, sapon. with BuCHEtCO2Na in aq.Some commonly used reagents like 104146-10-3 is used in this experiment. MeCOMe and esterification with ICH2O2CCMe3 in DMF. ..