http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-1254907-A

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filingDate 1969-11-21-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_f5bdc0befff10b6e0b874de740cafbf0
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_4b5bb8696ff3da9c735480865fd6cec1
publicationDate 1971-11-24-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1254907-A
titleOfInvention Indenyloxy and indenylthio alkanoic acids
abstract 1,254,907. Indenyloxy- and indenylthioalkanoic acids. MERCK & CO. Inc. 21 Nov., 1969 [25 Nov., 1968], No. 57071/69. Heading C2C. Novel compounds of Formula I where Y is an alkylene or haloalkylene radical; A is an oxygen or sulphur atom; R is a C 1-5 alkyl, cycloalkyl, mononuclear aryl, mononuclear aralkyl, halo-substituted mononuclear; aralkyl or trifluoromethyl-substituted C 1-5 alkyl radical; R<SP>1</SP> is a hydrogen atom or a C 1-5 alkyl or mononuclear aryl radical; m is 1, 2 or 3; and each X is a halogen atom or a C 1-5 alkyl, trifluoromethyl or acylamino radical or two X radicals on adjacent carbon atoms of the benzene ring are joined to form a trimethylene, tetramethylene or 1,3-butadienylene chain and salts, esters and amides thereof, are prepared by one of the following methods: (a) a novel intermediate of Formula VII where R<SP>2</SP> is C 1-5 alkyl is treated with a base and optionally hydrolysed.to the free acid; (b) a compound of Formula II is dehydrohalogenated by means of an organic base or if R is methyl by means of LiBr; or (c) a compound of Formula III is reacted with a compound of formula Z-Y<SP>1</SP>-COOM where Z is Cl or Br, Y<SP>1</SP> is methylene or trimethylene and M is H, a metal atom or a C 1-5 alkyl radical optionally followed by acid hydrolysis and, in all cases, optionally followed by salt, ester or amide formation. Novel compounds of Formula VII above are prepared by reaction of a compound of Formula X with N-bromosuccinimide. Intermediates of Formula II above are prepared by halogenation of a compound of Formula V which are prepared by cyclization of a compound of Formula VIII Intermediates of Formula III above are prepared by cyclization of a compound of Formula XII followed by halogenation and dehydrohalogenation steps similar to those necessary to convert compounds of Formula VIII to compounds of Formula I. [2 - Chloro - 4 -( 2 - methylenebutyryl) - phenozy]-acetic acid is prepared by action of aqueous NaHCO 3 on [2-chloro-4-(2-dimethylaminomethylbutyryl)-phenoxy]-acetic acid hydrochlcride prepared by reacting 2-chloro-4-butyrylphenoxy acetic acid, paraformaldehyde and dimethylamine hydrochloride [2-Chloro-4-butyrylphenoxy acetic acid is prepared by reaction of butyryl chloride and ochlorophenoxy acetic acid. Pharmaceutical compositions in conventional forms for oral or parenteral administration and having diuretic and saluretic effects comprise an above novel compound of Formula I or a derivative thereof and a carrier or diluent therefor.
isCitedBy http://rdf.ncbi.nlm.nih.gov/pubchem/patent/DE-2463215-C2
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priorityDate 1968-11-25-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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