GB721286A - Improvements in or relating to the preparation of tetrahydroisoquinolone derivatives - Google Patents
Improvements in or relating to the preparation of tetrahydroisoquinolone derivativesInfo
- Publication number
- GB721286A GB721286A GB58/52A GB5852A GB721286A GB 721286 A GB721286 A GB 721286A GB 58/52 A GB58/52 A GB 58/52A GB 5852 A GB5852 A GB 5852A GB 721286 A GB721286 A GB 721286A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isocyanate
- phenyl
- butyl
- prepared
- hydrogen
- 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
Links
Abstract
Tetrahydroisoquinolines of the general formula <FORM:0721286/IV (b)/1> (wherein Y is hydrogen or a lower alkyl or lower alkoxy group having not more than 10 carbon atoms, R1 is hydrogen, or a lower alkyl group having not more than 10 carbon atoms, and R is hydrogen, a lower alkyl group having not more than 10 carbons, a phenyl group or a benzyl group) are prepared by treating a b -phenylethyl isocyanate of the structure <FORM:0721286/IV (b)/2> or a b -phenyl ethyl carbamyl chloride of the structure <FORM:0721286/IV (b)/3> (in which Y, R and R1 are as given) with a Friedel-Crafts type of condensing agent, preferably in the presence of an inert solvent. In examples: (1) 1-phenyl hexane isocyanate in nitrobenzene is treated with anhydrous aluminium chloride to yield 3-butyl-tetrahydro isoquinolone-1. In a similar manner the following tetrahydroisoquinolones are prepared: 3-ethylfrom 1-phenylbutane isocyanate-2; 3-methylfrom b -phenyl-isopropylisocyanate; 3-benzylfrom 1 : 3-diphenylpropyl-isocyanate-2; 3-phenylfrom 1 : 2-diphenylethyl-isocyanate; 7-butylfrom b -(p-butylphenyl)-ethyl isocyanate; 3-methyl-7-methoxyfrom b -(p-methoxyphenyl) - isopropyl - isocyanate; 4 - methyl from 2 - phenylpropyl - 1 - isocyanate; 4 - ethyl-from 2-phenyl-butyl-1-isocyanate; 4-iso-propylfrom 2-phenyl-3-methylbutyl isocyanate; 7-methoxy-3 : 4-dimethylfrom 2-(p-methoxy-phenyl) - 3 - isocyanobutane; 7-butyl - 3 : 4 - dimethyl - from 2 - (p - butylphenyl) - 3 - isocyanobutane; and 4 : 8 - dimethyl-3-butyl from 2-(m-tolyl)-3-isocyanohexane; (2) b -phenyl isopropylamine in nitrobenzene is saturated with hydrogen chloride and then treated with phosgene to produce the corresponding carbamyl chloride which on treatment with aluminium chloride yields 3-methyl tetrahydro-isoquinolone-1. The 7-butyl tetrahydro-isoquinolone is similarly prepared from b -(p-butylphenyl)-ethylamine. The intermediate b -phenylethyl isocyanates are prepared from the corresponding amines by treatment with phosgene in an inert solvent. Dibenzyl carbinamine is prepared from dibenzyl ketone, formic acid and formamide; b -(p-butyl-phenyl)-ethylamine from chloromethylated butyl benzene by treatment with alcoholic potassium cyanide and reduction with Raney nickel.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US721286XA | 1951-02-16 | 1951-02-16 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB721286A true GB721286A (en) | 1955-01-05 |
Family
ID=22105764
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB58/52A Expired GB721286A (en) | 1951-02-16 | 1952-01-01 | Improvements in or relating to the preparation of tetrahydroisoquinolone derivatives |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB721286A (en) |
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0355750A1 (en) * | 1988-08-19 | 1990-02-28 | Warner-Lambert Company | Substituted dihydroisoquinolinones and related compounds as potentiators of the lethal effects of radiation and certain chemotherapeutic agents; selected compounds, analogs and process |
US5177075A (en) * | 1988-08-19 | 1993-01-05 | Warner-Lambert Company | Substituted dihydroisoquinolinones and related compounds as potentiators of the lethal effects of radiation and certain chemotherapeutic agents; selected compounds, analogs and process |
WO2002090334A1 (en) * | 2001-05-08 | 2002-11-14 | Kudos Pharmaceuticals Limited | Isoquinolinone derivatives as parp inhibitors |
US7196085B2 (en) | 2002-04-30 | 2007-03-27 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
US7407957B2 (en) | 2004-08-26 | 2008-08-05 | Maybridge Limited | Phthalazinone derivatives |
US7449464B2 (en) | 2003-03-12 | 2008-11-11 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
US7470688B2 (en) | 2005-10-19 | 2008-12-30 | Maybridge Limited | Phthalazinone derivatives |
US7750006B2 (en) | 2000-10-30 | 2010-07-06 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
US7981890B2 (en) | 2007-09-14 | 2011-07-19 | Astrazeneca Ab | Phthalazinone derivatives |
US8129380B2 (en) | 2008-01-23 | 2012-03-06 | Astrazeneca Ab | Phthalazinone derivatives |
US8183369B2 (en) | 2007-10-17 | 2012-05-22 | Kudos Pharmaceuticals Limited | 4- [3- (4-cyclopropanecarbonyl-piperazine-I-carbonyl) -4 -fluoro-benzyl] -2H-phthalaz in-1-one |
US8912187B2 (en) | 2003-03-12 | 2014-12-16 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
-
1952
- 1952-01-01 GB GB58/52A patent/GB721286A/en not_active Expired
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5177075A (en) * | 1988-08-19 | 1993-01-05 | Warner-Lambert Company | Substituted dihydroisoquinolinones and related compounds as potentiators of the lethal effects of radiation and certain chemotherapeutic agents; selected compounds, analogs and process |
EP0355750A1 (en) * | 1988-08-19 | 1990-02-28 | Warner-Lambert Company | Substituted dihydroisoquinolinones and related compounds as potentiators of the lethal effects of radiation and certain chemotherapeutic agents; selected compounds, analogs and process |
US7750006B2 (en) | 2000-10-30 | 2010-07-06 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
WO2002090334A1 (en) * | 2001-05-08 | 2002-11-14 | Kudos Pharmaceuticals Limited | Isoquinolinone derivatives as parp inhibitors |
US6664269B2 (en) | 2001-05-08 | 2003-12-16 | Maybridge Plc | Isoquinolinone derivatives |
US7196085B2 (en) | 2002-04-30 | 2007-03-27 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
US8912187B2 (en) | 2003-03-12 | 2014-12-16 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
US9169235B2 (en) | 2003-03-12 | 2015-10-27 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
US7662818B2 (en) | 2003-03-12 | 2010-02-16 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
US11160803B2 (en) | 2003-03-12 | 2021-11-02 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
US7449464B2 (en) | 2003-03-12 | 2008-11-11 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
US10449192B2 (en) | 2003-03-12 | 2019-10-22 | Kudo Pharmaceuticals Limited | Phthalazinone derivatives |
US9566276B2 (en) | 2003-03-12 | 2017-02-14 | Kudos Pharmaceuticals Limited | Phthalazinone derivatives |
US7407957B2 (en) | 2004-08-26 | 2008-08-05 | Maybridge Limited | Phthalazinone derivatives |
US7666870B2 (en) | 2004-08-26 | 2010-02-23 | Maybridge Limited | Phthalazinone derivatives |
US7470688B2 (en) | 2005-10-19 | 2008-12-30 | Maybridge Limited | Phthalazinone derivatives |
US7902193B2 (en) | 2005-10-19 | 2011-03-08 | Maybridge Limited | Phthalazinone derivatives |
US7981890B2 (en) | 2007-09-14 | 2011-07-19 | Astrazeneca Ab | Phthalazinone derivatives |
US8183369B2 (en) | 2007-10-17 | 2012-05-22 | Kudos Pharmaceuticals Limited | 4- [3- (4-cyclopropanecarbonyl-piperazine-I-carbonyl) -4 -fluoro-benzyl] -2H-phthalaz in-1-one |
US8129380B2 (en) | 2008-01-23 | 2012-03-06 | Astrazeneca Ab | Phthalazinone derivatives |
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