Reference

Preparation of Na-carboxycycloalkanoyl amino acid amides and analogs as matrix metalloproteinase inhibitors

Hagmann, William K.; Caldwell, Charles G.; Gooley, Paul R. (Merck and Co., Inc., USA). Brit. UK Pat. Appl. GB 2282598 A1 12 Apr 1995, 85 pp. (United Kingdom). CODEN: BAXXDU. CLASS: ICM: C07C235-82. ICS: A61K031-19; A61K031-215. APPLICATION: GB 94-20114 5 Oct 1994. PRIORITY: US 93-133493 8 Oct 1993. DOCUMENT TYPE: Patent CA Section: 34 (Amino Acids, Peptides, and Proteins) Section cross-reference(s): 1 Title compds. [I; R = Ph, naphthyl, pyridyl, quinolyl, etc.; R1 = OH, NHOH, alkoxy, etc.; R2 = H, alk(en)yl, alkoxy, etc.Except for chemicals metioned above, 52186-89-7 is also used.; R3 = (di)alkylamino, NHCRfRgCONR6R7; R6,R7 = H, alkyl, (hetero)aryl, etc.; Rf,Rg = H, (un)substituted alkyl, etc.; n = 1-4; p = 1 or 2] were prepd. as matrix metalloproteinase inhibitors (no data). Thus, 4-PrC6H4CH2CH2CH(CHO)CO2CMe3 (prepn. given) was cyclocondensed with [1-(ethoxycarbonyl)cyclopropyl]triphenylphosphonium tetrafluoroborate to give, after hydrogenation, I (R = 4-PrC6H4, R2 = H, n = 2, p = 1)(II; R1 = OEt, R3 = OCMe3, R4R5 = bond) which was converted in 6 addnl. steps to II [R1 = OH, R3 = (S)-NHCH(CHMe2)CONHPh]. .