Pharmaceutical Substances Syntheses, Patents, Applications - Part 191. Reference containing a collection of 2267 active pharmaceutical ingredients, including those launched recently. Listed alphabetically according to their INNs and established a link between INNs, structure, synthesis and production processes, patent and literature situation, medical use, and trade names. For pharmacists and researchers. | Stavudine S 1901 1. Zn 2. 3. ion exchange 2. butylamine 0 HN H3 Stavudine 1. Zn HBr CH3COOH 111 IV -------------------- V 2. H2NXX CH3 3. ion exchange Stavudine CH3 0 Cl 0 0 9 U 11 H C O CH. 0 ch3 1 2-0-isopropylidene- benzoyl VU a-D-xylof uronose chloride VIII RO 1 2 3-tri-0-acetyl-5- O-benzoyl-a-D-xylo-furanose VIII 0 R CHj Tms 1. SnCI4 CH3CN 2. H2S04 CH3CN 65-77 C OH Tms -CH -ch3 bis trimethyl-silyQthymine DC X 1O 2. Nol H3C 0-- -0 ch 100-150 C 3. CHjONo. CHjOH 3 Stavudine 1902 S Stavudine OH 2. NoOH C2H5OH tBuOK DM SO Stovudine thymidine 1- JL CF SO H TmsZ ms Tms-CI CH3CN 2. NaOCHj CH-jOH x 1. hexamethyldisilazane thymine 2 3 5-tri-O-benzoyl-a-D-ribofuranosyl acetate H 1. H3C-C0 20 HN if 3 2 Zr 2 ho lOj br 3- c4h9 jn OH OH XI Stavudine 1. DMF - S -5-hydroxy-y-valerolactone tert-butyldiphenyl silyl chloride 2. I H3C N CHj . THF CH-jCHj 3. 0 0 hmpt 2. lithium diisopropylamide 3. diphenyl sulfide XII XII H Cx CH3 1. ô T Al T ô . toluene ch3 h ch3 2. H3C-CO 20 J 3. IX SnCI4. CH2CI2 1. diisobutylaluminum hydride xin Stavudine S 1903 Mil 1. Nqĩo4 THF H2O 3. Bu4N F THF 1. sodium periodate Stovudine Reference s synthesis EP334 368 Bristol-Myers Squibb appl. USA-prior. . EP 653 436 Bristol-Myers Squibb appl. USA-prior. . RU 2 047 619 Institut Organicheskoj Khimii Ufimskogo Nauchnogo TsentraRan. appl. RU-prior. . JP07 278 178 Nippon Tobacco Sangyo appl. J-prior. . EP 501 511 Bristol-Myers Squibb appl. USA-prior. . JP04 054 193 Nippon Tobacco Sangyo appl. J-prior. . WO 9 202 516 Japan Tobacco Inc. appl. J-prior. . WO 9 209 599 Yamasa Shoyu appl. J-prior. . EP 519 464 Ajinomoto Co. appl. J-prior. . JP04 226 976 Japan Tobacco Inc. appl. J-prior. . US 5 175 267 University of Georgia Res. Found. appl. USA-prior. . Horwitz . et
