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Novel 6,7-disubstituted-isoquinoline derivatives and their use

A technology of dihydroisoquinoline and medicine, which can be applied to medical preparations containing active ingredients, pharmaceutical combinations, active ingredients of heterocyclic compounds, etc., and can solve problems such as high concentration

Inactive Publication Date: 2013-06-26
MONTISERA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Acetaldehyde is also self-administered when it is injected intracranially, but at much higher concentrations

Method used

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  • Novel 6,7-disubstituted-isoquinoline derivatives and their use
  • Novel 6,7-disubstituted-isoquinoline derivatives and their use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] 6,7-Difluoro-1-methyl-3,4-dihydroisoquinoline

[0070] 1H NMR(CDCl3): δppm 7.450(3,1H,d,J=4.858), 2.277(6,3H), 3.647(8,1H,ddd, J=13.253, J=9.980, J=3.970), 3.848 (8,1H,ddd,J=13.253,J=3.860,J=1.950),3.019(9,1H,ddd,J=14.326,J=3.970,J=1.950),2.849(9,1H,ddd,J =14.326,J=9.980,J=3.860), 7.260(11,1H,d,J=4.858). The boiling point is 112-116°C at 10mmHg.

Embodiment 2

[0072] 1-Methyl-4,6,7-trifluoro-3,4-dihydroisoquinoline

[0073] 1H NMR(CDCl3): δppm 7.493(3,1H,d,J=5.422), 2.238(6,3H), 3.886(8,1H,dd,J=13.927,J=3.970), 3.943(8,1H) ,dd,J=13.927,J=1.960), 5.884(9,1H,dd,J=3.970,J=1.960), 7.763(12,1H,d,J=5.422). The boiling point is 118-122°C at 10mmHg.

Embodiment 3

[0075] 4,6,7-Trifluoro-1-methyl-1,2,3,4-tetrahydroisoquinoline

[0076] 1H NMR(CDCl3): δppm 7.466(3,1H,d,J=5.020), 3.930(5,1H,q,J=6.684), 1.213(6,3H,d,J=6.684), 3.065(8 ,1H,dd,J=14.188,J=3.650), 3.089(8,1H,dd,J=14.188,J=2.050), 5.788(9,1H,dd,J=3.650,J=2.050), 7.602( 12,1H,d,J=5.020). The boiling point is 108-113°C at 10mmHg.

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Abstract

The present invention relates compounds of general formula (I) and stereoisomers and pharmaceutically acceptable salts and prodrugs thereof; wherein R' and R1 - R5 are as defined in the claims. The invention also relates to said compounds for use as a medicament and particularly in the treatment of drug addiction and CNS related diseases.

Description

technical field [0001] The present invention relates to novel 6,7-disubstituted isoquinoline derivatives, and more particularly, the present invention relates to novel 6,7-disubstituted-1-methyl-1,2,3,4-tetrahydro- and -3,4-dihydroisoquinoline derivatives and pharmaceutical compositions comprising the same. The present invention also relates to said compounds for use in the treatment of drug addiction and CNS-related diseases. Background technique [0002] Endogenous isoquinolines are formed by the condensation of biogenic amines such as phenethylamine with simple aldehydes such as formaldehyde or acetaldehyde. They are known to modulate neurotransmission, central metabolism and motor activity. The endogenous TIQ derivative salsolinol (1-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol) is thought to be a causative factor in Parkinson's disease (PD), and according to (R)-1-MeTIQ (1-methyl-1,2,3,4-tetrahydroisoquinoline) was shown to have anti-Parkinsonian activity. Until r...

Claims

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Application Information

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IPC IPC(8): A61K31/47A61P25/16
CPCA61K31/472A61P25/00A61P25/16A61P25/28A61P25/30C07D217/02C07D217/22A61K31/47
Inventor 维尔·陶科马蒂·埃克霍尔姆
Owner MONTISERA
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