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filingDate 1975-04-25-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_e312f7feac2b727994d59c28ef244102
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publicationDate 1982-11-26-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber CS-216827-B2
titleOfInvention Method of making the phenylalkylamine
abstract 1501436 Aralkylamine derivatives BOEHRINGER INGELHEIM GmbH 25 April 1975 [27 April 1974] 17328/75 Heading C2C Novel compounds of Formula I [wherein R 1 represents a hydrogen atom, the group -(CH 2 ) n -R 4 (wherein n is 1 or 2 and R 4 represents a hydrogen atom, or a cyano or benzoyl group) or the group -CO-R 5 (wherein R 5 represents a hydrogen atom, a C 1 -C 4 alkoxy group, a benzoyl or benzyloxy group, or a group of the formula -CH 2 -NH 2 , -CH(CH 3 )-NH 2 , R 2 represents a hydrogen atom or a methyl group; and R 3 represents a nitro or amino group or the group -NH-CO-R 6 (wherein R 6 represents a hydrogen atom, a methyl, methoxy, ethoxy, methylthio or ethylthio group) or the group -NH-W-R 7 (wherein R 7 represents an amino, methylamino or dimethylamino group and W represents the group -CO- or -SO 2 -)] and acid addition salts thereof, with the provisos that R 3 is other than amino when R 1 and R 2 are both hydrogen and other than nitro when R 1 and R 2 are both methyl, are prepared by one of the following methods: (a) a compound of Formula II is reacted with R 6 COX or R 7 W-X where X is an atom or group removable as an anion; (b) reduction of a compound of Formula IIIa or IIIb where Y is H, CH 2 , C 2 H 5 , OH, NH 2 or NH 2 CONH- with a complex hydride or by catalytic hydrogenation and the compounds IIIa and IIIb may be prepared in situ from compounds of FormulĀµ IVa or IVb which may be obtained from the amino compounds by the method of (a) above, (c) compounds of FormulĀµ VIa and VIb where Z is a halogen atom is reduced by catalytic hydrogenation; (d) a compound of Formula VII is reacted with R 1 X provided R 1 is not H; (e) a compound of Formula VIIc is reacted with R 4 (CH 2 ) n X and R 8 H is removed by alkaline hydrolysis; (f) hydrogenation of a compound of Formula VIIIa or VIIIb wherein Q is -NR 9 R 10 , where R 9 is H or an amino protecting group removable by hydrogenation and R 10 is H, CH 2 , C 2 H 5 , COCH 2 NHR 11 or COCH(CH 3 )NHR 11 , where R 11 is H or an amino protecting group removable by hydrogenation; (g) hydrolysls of a compound of Formula IX wherein R 12 is an acyl group; or (h) hydrolysis or hydrogenation of a compound of Formula X wherein R 14 is benzyl carbobenzoxy or acyl. Several intermediates and starting materials in the above processes a-g are also prepared and isolated. Pharmaceutical compositions in conventional forms for oral, rectal and parenteral administration having use in increasing blood pressure and having sympathomimetic activity in the central nervous system comprise an above novel compound and a carrier or diluent.
priorityDate 1974-04-27-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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