GB674800A - Improvements in or relating to alkoxybenzylisoquinolines and salts thereof - Google Patents

Improvements in or relating to alkoxybenzylisoquinolines and salts thereof

Info

Publication number
GB674800A
GB674800A GB22456/50A GB2245650A GB674800A GB 674800 A GB674800 A GB 674800A GB 22456/50 A GB22456/50 A GB 22456/50A GB 2245650 A GB2245650 A GB 2245650A GB 674800 A GB674800 A GB 674800A
Authority
GB
United Kingdom
Prior art keywords
methoxy
ethoxy
salts
acids
alkoxyphenylacetamides
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB22456/50A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of GB674800A publication Critical patent/GB674800A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D217/00Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/18Aralkyl radicals
    • C07D217/20Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

The invention comprises alkoxybenzyl-isoquinolines of the formula <FORM:0674800/IV (b)/1> where R1 and R2 are different alkoxy radicals of 1-3 carbon atoms, one being methoxy, and their addition salts; they are prepared by ringclosure of the appropriate a -methyl-homoveratryl-alkoxyphenylacetamides with phosphorus oxychloride and dehydrogenation of the resulting 3 : 4-dihydro-isoquinolines, e.g. with palladium. The products form salts with mineral and organic acids, e.g. with hydrochloric, hydrobromic, hydriodic, sulphuric, nitric, phosphoric and citric acids. Examples show the production of the 31-ethoxy-41-methoxy, 41-ethoxy-31-methoxy and 31-methoxy-41-isopropoxy compounds and their salts. a -Methylhomoveratrylamine is made by (1) addition of hydrogen bromide to eugenol methyl ether, followed by treatment with ammonia, or (2) catalytic hydrogenation of 1 - (31 : 41 - dimethoxyphenyl) - 2 - propanone oxime, prepared from the ketone in the usual way. a - Methylhomoveratryl - alkoxyphenylacetamides are made by reacting the above amine with the appropriate alkoxyphenylacetic acids, e.g. the 3-ethoxy-4-methoxy, 4-ethoxy-3-methoxy and 3-methoxy-4-isopropoxy-acids.
GB22456/50A 1949-11-09 1950-09-12 Improvements in or relating to alkoxybenzylisoquinolines and salts thereof Expired GB674800A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US674800XA 1949-11-09 1949-11-09

Publications (1)

Publication Number Publication Date
GB674800A true GB674800A (en) 1952-07-02

Family

ID=22076271

Family Applications (1)

Application Number Title Priority Date Filing Date
GB22456/50A Expired GB674800A (en) 1949-11-09 1950-09-12 Improvements in or relating to alkoxybenzylisoquinolines and salts thereof

Country Status (1)

Country Link
GB (1) GB674800A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013078413A1 (en) * 2011-11-22 2013-05-30 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Modulators of lipid storage

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013078413A1 (en) * 2011-11-22 2013-05-30 The United States Of America, As Represented By The Secretary, Department Of Health And Human Services Modulators of lipid storage

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