Title:
ISOQUINOLINE -1,3,4-TRIONE, THE SYNTHETIC METHOD AND THE USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2004/111010
Kind Code:
A1
Abstract:
The invention relates to all types of substituted isoquinoline -1,3,4-trione, the synthetic method thereof and the use for treatding neurodegenerative diseases , especially as the medicine for Alzhermer's disease, appplexy and brain ischernic injuries, the compound is represented by the structure, Formula (I); Dihydroisoquinoline-1,3,4-trione) wherein substituents R, can be one , two or three groups optionally selected from the group consisting of H; alkyl; hydroxyl; alkyl substituted by the groups including halogen , alkoxyl, hydroxyl; alkyl or alkylamine substituted by the groups including halogen , alkoxyl, hydroxyl; C,-,alkenyl substituted by oxygen or amine; C, 6cycloalkyl; substituted aryl; benzyl; alkanoyl; alkanoyl substituted by the groups including halogen , alkoxyl, hydroxyl; C2-6enc,yl ; C,-,cycloalkanoyl; tertÂbutoxycarbonyl; benzoyl; benzoyl. substituted by one, two or three groups including alkylarnine; benzylacryl; benzylacryl. substituted by one, two or three groups including alkylamine; thienylfonnyl; admantyliForrnyl; mandeloyl; alkoxyl; alkylamine; cycloalkoxyl; cycloalkoxycarbonyl; alkanoylxy; alkanoylamine; cycloalkyanoylxy; cycloalkanoylarnine; ureido; urenylene; alkanoyl; nitro; carboxyl; R2 is H; alkyl; alkyl. or Cl-C4cycloalkyl which are substituted by the groups including halogen, alkoxyl, hydroxyl; C2-C,alkenyl; acryl; substituted acryl; X is H, CH2, N-H, 0, S; is CH, N.
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Inventors:
NAN FAJUN (CN)
LI JIA (CN)
CHEN YIHUA (CN)
ZHANG YAHUI (CN)
GU MIN (CN)
ZHANG HUAJIE (CN)
LI JIA (CN)
CHEN YIHUA (CN)
ZHANG YAHUI (CN)
GU MIN (CN)
ZHANG HUAJIE (CN)
Application Number:
PCT/CN2004/000567
Publication Date:
December 23, 2004
Filing Date:
May 31, 2004
Export Citation:
Assignee:
SHANGHAI INST MATERIA MEDICA (CN)
NAN FAJUN (CN)
LI JIA (CN)
CHEN YIHUA (CN)
ZHANG YAHUI (CN)
GU MIN (CN)
ZHANG HUAJIE (CN)
NAN FAJUN (CN)
LI JIA (CN)
CHEN YIHUA (CN)
ZHANG YAHUI (CN)
GU MIN (CN)
ZHANG HUAJIE (CN)
International Classes:
A61P25/00; A61P25/28; C07D217/24; C07D417/04; (IPC1-7): C07D217/04; A61P25/00; A61P25/28
Other References:
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DATABASE CA [online] GLYNN M. ET AL.: "1,3,4(2H)-isoquinolinetriones: evaluation of amino-substituted derivatives as redox mediator herbicides", XP002983933, accession no. STN Database accession no. 132:190817
LING K.Q. ET AL.: "On the reactions of 1,3-isoquinolinediones with singlet oxygen", TETRAHEDRON, vol. 55, no. 30, 1999, pages 9185 - 9204, XP004172253
DATABASE CA [online] 2000, MAZZA MARCO ET AL.: "Herbicidal activity of 2-substituted 1,3,4-(2H)-isoquinolinetriones", XP002983934, accession no. STN Database accession no. 131:181047
DATABASE CA [online] 1999, LING K.Q. ET AL.: "Dye-sensitized photooxygenations of 1,3-isoquinilinediones", XP002983935, accession no. STN Database accession no. 128:321547
DATABASE CA [online] 1999, POLLERS-WIEERS C. ET AL.: "The use of isoquinolinetriones in the synthesis of benzo[c]phenanthridine alkaloids", XP002983936, accession no. STN Database accession no. 97:6594
VEKEMANS JOZEF ET AL.: "A new path to 1,3,4(2H)-isoquinolinetriones and substituted isoindolinones", TETRAHEDRON, vol. 36, no. 7, 1980, pages 943 - 950, XP002983937
BUU-HOI N.P. ET AL.: "Phthalonimides(1,3,4-trioxo-1,2,3,4-tetrahydroisoquinolines) of potential biological interest", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 5, no. 4, 1968, pages 545 - 547, XP000906859
"Apoptosis: Pharmacological Implications and Therapeutic Opportunities", 1997, ACADEMIC PRESS
"When Cells Die", 1998, WILEY-LISS
CELL, vol. 75, 1993, pages 641 - 652
SCIENCE, vol. 263, 1994, pages 826 - 828
CHEN J; NAGAYAMA T; JIN K ET AL., J NEUROSCI, vol. 18, no. 13, 1998, pages 4914 - 4928
NAMURA S; ZHU J; FINK K ET AL., J NEUROSCI, vol. 18, no. 10, 1998, pages 3659 - 3668
BEER R; FRANZ G; SRINIVASAN A ET AL., J NEUROCHEM, vol. 75, no. 3, 2000, pages 1264 - 1273
MA J; ENDRES M; MOSKOWITZ MA, BR J PHARMACOL, vol. 124, no. 4, 1998, pages 756 - 762
GARCIA-CALVO, M. ET AL., J. BIOL. CHEM., vol. 273, 1998, pages 32608 - 32613
SCHOTTE, P. ET AL., FEBR LETT., vol. 442, 1999, pages 117 - 121
MANSKE, R. H. F.: "Benzyl Phthalimide", ORGANIC SYNTHESES, vol. 2, pages 83 - 84
DATABASE CA [online] GLYNN M. ET AL.: "1,3,4(2H)-isoquinolinetriones: evaluation of amino-substituted derivatives as redox mediator herbicides", XP002983933, accession no. STN Database accession no. 132:190817
LING K.Q. ET AL.: "On the reactions of 1,3-isoquinolinediones with singlet oxygen", TETRAHEDRON, vol. 55, no. 30, 1999, pages 9185 - 9204, XP004172253
DATABASE CA [online] 2000, MAZZA MARCO ET AL.: "Herbicidal activity of 2-substituted 1,3,4-(2H)-isoquinolinetriones", XP002983934, accession no. STN Database accession no. 131:181047
DATABASE CA [online] 1999, LING K.Q. ET AL.: "Dye-sensitized photooxygenations of 1,3-isoquinilinediones", XP002983935, accession no. STN Database accession no. 128:321547
DATABASE CA [online] 1999, POLLERS-WIEERS C. ET AL.: "The use of isoquinolinetriones in the synthesis of benzo[c]phenanthridine alkaloids", XP002983936, accession no. STN Database accession no. 97:6594
VEKEMANS JOZEF ET AL.: "A new path to 1,3,4(2H)-isoquinolinetriones and substituted isoindolinones", TETRAHEDRON, vol. 36, no. 7, 1980, pages 943 - 950, XP002983937
BUU-HOI N.P. ET AL.: "Phthalonimides(1,3,4-trioxo-1,2,3,4-tetrahydroisoquinolines) of potential biological interest", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 5, no. 4, 1968, pages 545 - 547, XP000906859
"Apoptosis: Pharmacological Implications and Therapeutic Opportunities", 1997, ACADEMIC PRESS
"When Cells Die", 1998, WILEY-LISS
CELL, vol. 75, 1993, pages 641 - 652
SCIENCE, vol. 263, 1994, pages 826 - 828
CHEN J; NAGAYAMA T; JIN K ET AL., J NEUROSCI, vol. 18, no. 13, 1998, pages 4914 - 4928
NAMURA S; ZHU J; FINK K ET AL., J NEUROSCI, vol. 18, no. 10, 1998, pages 3659 - 3668
BEER R; FRANZ G; SRINIVASAN A ET AL., J NEUROCHEM, vol. 75, no. 3, 2000, pages 1264 - 1273
MA J; ENDRES M; MOSKOWITZ MA, BR J PHARMACOL, vol. 124, no. 4, 1998, pages 756 - 762
GARCIA-CALVO, M. ET AL., J. BIOL. CHEM., vol. 273, 1998, pages 32608 - 32613
SCHOTTE, P. ET AL., FEBR LETT., vol. 442, 1999, pages 117 - 121
MANSKE, R. H. F.: "Benzyl Phthalimide", ORGANIC SYNTHESES, vol. 2, pages 83 - 84
Attorney, Agent or Firm:
SHANGHAI KAIJI INTELLECTUAL PROPERTY AGENT CO., LTD. (188 Nandandong Road, Shanghai 0, CN)
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