Organic Chemistry of Drug Synthesis. Volume 7

Adding yet another large substituent to the imidazole ring restores PDE inhibiting activity. The resulting compounddasantafil( 1 ...

skeleton ( 136 ). Saponification of the acetate group on the pendant side chain then affords the PDE V inhibitor 137.^20 Moving ...

The peptide hormone, glucagon-like peptide (GLP-1), which is released in response to intake of food, regulates insulin levels. T ...

N N OCH 3 OCH 3 F F F Br F F F 154 155 N N OCH 3 OCH 3 H 3 O+ 2.t-BOC 2 O F F F OH NHt-BOC NHt-BOC NH t-BOC NHt-BOC NHt-BOC O ...

leave behind a hydroxyl group. Acid hydrolysis then opens the acetonide to afford the immune system stimulant 170.^24 CO 2 CH 3 ...

with chloroacetonitrile affords 174. Treatment of 174 with Raney nickel reduces the cyano group to the corresponding primary ami ...

N O NH 181 N O N 182 O NH 2 O N NH 2 183 OCH 3 F F ON N O N F N OCH 3 N O N O N F N OH 185 184 The structure of a recent quinolo ...

186 C 2 H 5 O 2 CNH 2 + CN C^2 H^5 O^2 C NH 187 NaH O NH NC 188 NC (tBuOC) 2 O O NCOtBu NC 189 NaBH 4 HO NCOtBu NC 190 LiAlH ...

methylene–propargyl group. Alkylation of the enolate from dimethylho- motetrephthalate ( 197 ) with propargyl bromide attaches t ...

The fact that the final compound will contain chiral atoms at two remote locations on the fused piperidine ring and on the yet-t ...

thiadiazole carboxylic acid ( 214 ). The hydroxyl group in the product ( 216 ) is then oxidized with manganese dioxide to afford ...

NH HO CO 2 H 221 N HO CO 2 H P O iPrO iPrO 222 (Ph 2 PO) 2 O N HO iPrOiPrOPO 223 POPh 2 O CH 3 SO 2 Cl N CH 3 SO 2 P O iPrO iPrO ...

A. Graul, J. Castaner,Drugs Future 22 , 945 (1997). A.V. Averola, J.M.P. Soto, J.M. Mauri, R.W. Gristwood, U.S. Patent 5,223,50 ...

CHAPTER 10 POLYCYCLIC FUSED HETEROCYCLES A number of compounds defy ready assignment to one of the structural categories that ha ...

agents is not restricted to eukaryotic cells; the compounds also inactivate microbes. A recent nitrogen mustard-containing compo ...

activates liver enzymes that metabolize fatty acids thus lowering serum tri- glyceride levels. Reaction of the lithio reagent fr ...

proper ( 22 ) and butyllithium is treated with ethylene oxide. The hydroxyl group on the end of the ethyl group in 23 is next co ...

function, is next replaced by benzyl with successive saponification, and then alkylation of the resulting phenol with benzyl bro ...

the nitrobenzoyl chloride 38 proceeds in straightforward fashion to the amide ( 39 ). Reduction of the nitro group by means of h ...

ring fusion. The amide nitrogen in the product, which still contains a small amount of cis isomer, is next alkylated with methyl ...