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filingDate 1968-08-30-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationDate 1970-05-20-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber GB-1192138-A
titleOfInvention Novel Tetrahydro- quinoline Derivatives and a process for the manufacture thereof
abstract 1,192,138. 8-Alkoxyisoquinolines. F. HOFFMANN-LA ROCHE & CO. A.G. 30 Aug., 1968 [30 Aug., 1967], No. 41434/68. Heading C2C. The invention comprises compounds of formula wherein R<SP>1</SP> is C 1-7 alkyl and R<SP>2</SP> and R<SP>3</SP> are each H or C 1-7 alkyl, and their acid addition salts. These compounds are prepared by (a) reducing an 8-alkoxyisoquinoline or its quaternary salts, (b) reacting a 2-alkyl- or 1,2-dialkyl-8- hydroxy-1,2,3,4-tetrahydroisoquinoline, or a 2- alkyl - 8 - hydroxy - 3,4 - dihydroisoquinolinium salt with an alkylating agent, or (c) splitting off a protecting group in the 2-position from a (possibly 1-alkyl) 8-alkoxy-1,2,3,4-tetrahydroisoquinoline; and in each case, the base obtained may be converted to its acid addition salt. The invention comprises also the following analogues or derivatives of compounds of the above formula: (i) 3,4-dihydro analogues where R<SP>2</SP>=R<SP>3</SP>=H (prepared by oxidizing a starting material where R<SP>2</SP>=R<SP>3</SP>=H, with alkali metal hypohalite); (ii) 3,4-dihydro analogues of quaternized derivatives where R<SP>2</SP>=H and R<SP>3</SP>= C 1-7 alkyl or benzyl [prepared from products (i) with R<SP>3</SP>X (X = halogen)]; (iii) analogues where R<SP>2</SP> = H and R<SP>3</SP> = benzyl [prepared from products (ii) where R<SP>3</SP> = benzyl, with R<SP>2</SP>MgX]; (iv) 8-methoxyisoquinoline, its methodide and ethiodide [from 8-hydroxyisoquinoline with PhMe 3 N+Cl-, or with NaOMe (or NaOEt) followed by MeI (or EtI)]. Details are also given of the preparation of 8 - hydroxy - 1,2,3,4 - tetrahydroisoquinoline, 2- formyl - 8 - hydroxy - 1,2,3,4 - tetrahydroisoquinoline and its methyl ether, 8-hydroxyisoquinoline methiodide, 8 - hydroxy - 2 - methyl - 1,2,3, 4 - tetrahydroisoquinoline and 8 - ethoxyisoquinoline ethiodide. Therapeutic compositions for oral or parenteral administration comprise compounds of the above formula, which have vasodilator and blood pressure reducing properties, in association with a compatible pharmaceutical carrier.
priorityDate 1967-08-30-04:00^^<http://www.w3.org/2001/XMLSchema#date>
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Total number of triples: 39.