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US 8,013,184 B2Granted
Manufacture process of organic compounds
AssigneeNovartis AG
InventorBernhard Riss
Life of this patent
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Abstract
The present invention relates to a method of preparing N-substituted salicylamides or derivatives thereof and their derivatives, e.g. their salts. In particular, the present invention relates to a method of preparing (N-(5-chlorosalicyloyl)-8-aminocaprylic acid (5-CNAC) and its corresponding disodium monohydrate.
Claims15
A method for preparing a compound of formula IV:
- the method comprising
- (i) reacting a compound of formula I
- with a compound of formula II
- under basic conditions in which at least a portion of the phenolic hydroxy group is present in deprotonated form, in an aprotic solvent, to form a compound of formula III
- to form the compound of formula IV in the case where R7 is a carboxy group, or to form a compount of formula III in the case where R7 is not a carboxy group;
- (ii) converting R7 in the compound of formula III to a carboxy group to form the compound of formula IV;
- and wherein
- n is from 1 to 8;
- m is from 1 to 4;
- R1 is an alkyl group selected from methyl, ethyl, propyl, isopropyl and tert-butyl;
- each R2 is independently selected from —OH, NR3R4, halogen, C1, C2, C3 or C4 alkyl, C1, C2, C3 or C4 haloalkyl, C1, C2, C3 or C4 alkoxy, C2, C3 or C4 alkenyl;
- each R5 and each R6 are independently selected from Hydrogen, —OH, NR3R4, halogen, C1, C2, C3 or C4 alkyl, C1, C2, C3 or C4 alkoxy, C2, C3 or C4 alkenyl;
- R3 and R4 are each independently selected from hydrogen, —OH, C1, C2, C3 or C4 alkyl, C1, C2, C3 or C4 haloalkyl, C1, C2, C3 or C4 alkoxy, C2, C3 or C4 alkenyl;
- and
- R7 is a carboxylic acid or amide group or nitrile group.
12 more elements
Dependencies are inferred from the claim text.