IN WHICH: EACH OF X1 AND X2 WHICH MAY BE IDENTICAL OR DIFFERENT, REPRESENTS A CHLORINE, OR BROMINE ATOM, Y IS AS DEFINED UNDER X1 OR REPRESENTS A RADICAL OF FORFERENT, REPRESENTS A -O-AR-CH2X2 OR -O-AR'', EACH OF THE Y1 RADICALS, WHICH MAY BE IDENTICAL OR DIFFERENT REPRESENTS A -O-AR'' OR -O-AR-CH2X2 RADICAL, AR REPRESENTS A DIVALENT AROMATIC RADICAL, THE TWO FREE VALENCIES OF WHICH ARE CARRIED BY CARBON ATOMS OF ONE OR TWO AROMATIC BENZENE RINGS, AND AR'' REPRESENTS THE RADICAL -ARH THE UNITS (I) TO (V) BEING CONNECTED TO ONE ANOTHER VIA THE OXYGEN ATOM WITH A FREE VALENCY OF ONE OF THE UNITS AND A METHYLENE GROUP WITH A FREE VALENCY OF THE ADJACENT UNIT.
DAB IN WHICH Y-Z REPRESENTS AN AMINO ACID CHAIN SELECTED FROM D-LEU-THR,D-PHE-LEU, D-LEU-LEU AND D-LEU-ILEU, G REPRESENTS AN AMINO-PROTECTING RADICAL OF THE FORMULA:
PY-CH(-R)-OOC-
IN WHICH PY REPRESENTS PYRIDYL, PYRIDYL-N-OXIDE, OR PYRIDYL OR PYRIDYL-N-OXIDE CARRYING A METHYL SUBSTITUENT, R REPRESENTS HYDROGEN, ALKYL OF 1 TO THROUGH 5 CARBON ATOMS, OR PHENYL, AND DAB REPRESENTS A,Y-DIAMINOBUTYRIC AID, THE AMINO ACIDS HAVING THE L-CONFFIGURATION UNLESS OTHERWISE INDICATED, SAID CYCLOPEPTIDES CONTAINING ONLY A SINGLE FREE AMINO GROUP, ARE USEFUL INTERMEDIATES FOR THE SYNTHESIS OF SEMI-SYNTHETIC PRODUCTS DERIVED FROM POLYMYXINS.
Abstract:
D R A W I N G WHEREIN A is alkyl of three through 18 carbon atoms optionally substituted by hydroxy, amino or cyano; or alkyl of one through four carbon atoms substituted by a monocyclic or polycyclic alkyl radical or phenyl optionally substituted by halogen or alkoxy; or phenyl optionally substituted by halogen or alkoxy, X is -CO- or -SO2-, and Y-Z is one of the chains D-Phe-Leu, D-Leu-Leu and DLeu-Ileu, are prepared by introducing the grouping A-X-Dab-ThrDab- onto the appropriate cyclopeptide having its amino functions protected. New polymyxins of the said formula have antibiotic properties. Polymyxins of the formula
Abstract:
Ampicillin is prepared by reacting an inorganic or organic base with a new penicillin G derivative of the formula: OHS ¦ ANGLE CH3 C6H5-CH2-C---N----CH-CHC ANGLE ¦¦¦¦¦CH3 R2O-CS-NC=OO=C--N---CH-COOR1 ANGLE CH ¦ C6H5 (wherein R1 represents a group protecting the carboxy radical and R2 represents a strong electron-attracting group, e.g. a halogenoethyl group) to open the imidazolidine ring and give an intermediate product of the formula: S ANGLE CH3 R2O-CS-NH-CH-CONH----CH-CHC ANGLE ¦¦¦¦CH3 C6H5O=C--N---CH-COOR1 and removing by methods known per se the groups -R1 and R2O-CS- which protect the carboxy radical and amine functions respectively.
Abstract:
1454587 6-Trichloroacetamido-penicillanic acid derivatives RHONE-POULENC SA 5 Sept 1974 [6 Sept 1973] 38881/74 Heading C2C The invention comprises compounds of the formula wherein R is an ester radical. They may be obtained by either oxidizing the S-atom of a compound of the formula to a sulphoxide group, with, e.g. H 2 O 2 , NaIO 4 or an organic per-acid; or reacting a compound of the formula wherein R 1 is PhCH 2 or PhOCH 2 , with or a derivative thereof. Compounds of Formula II may be obtained either by reacting a compound of the formula with Cl 3 CCOOH or a derivative thereof or by reacting an imino-chloride of the above compound with an alkali metal salt of Cl 3 CCOOH. Compounds of Formula III may be obtained either by oxidation of a compound of Formula IV or by esterification of a compound of the formula
Abstract:
1454590 6-Chloroacetamido-penicillanic acid derivatives RHONE-POULENC SA 5 Sept 1974 [6 Sept 1973] 38884/74 Heading C2C The invention comprises compounds of the formula wherein R is an ester radical, e.g. C 1 -C 4 alkyl or benzyl which may be substituted by C 1- C 4 alkoxy. They may be obtained by treating a compound of the formula with Zn in acetic acid.