Novel 3-cyclopropylmethoxy-4-alkoxybenzamide PDE (phosphodiesterase) 4 inhibitors

An alkoxybenzamide, phosphodiesterase-like technology, applied in the directions of anti-inflammatory agents, non-central analgesics, antipyretics, etc., to achieve high in vitro enzyme inhibitory activity, good anti-inflammatory effect, good antidepressant effect of effect

Active Publication Date: 2016-04-27
兰晟生物医药(苏州)有限公司
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  • Application Information

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Problems solved by technology

It has been confirmed that PDE4 inhibitors have the effects of antidepressant and improving memory and cognition. For example, its subtype non-selective inhibitor rolipram (rolipram) can specifically enhance the cAMP signaling pathway, promote neurogenesis and improve plasticity, and rolipram The antidepressant and cognition-promoting effects and its strong and fast-acting characteristics have also been confirmed, but due to the adverse reactions of the digestive tract such as nausea and vomiting, it was terminated in the clinical trial stage

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  • Novel 3-cyclopropylmethoxy-4-alkoxybenzamide PDE (phosphodiesterase) 4 inhibitors

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Embodiment Construction

[0022] The present invention will be further described in detail below in conjunction with the accompanying drawings and embodiments.

[0023] Novel 3-cyclopropylmethoxy-4-alkoxybenzamide phosphodiesterase 4 inhibitor, said inhibitor is a compound represented by formula I or formula II, its prodrug, or Its pharmaceutically acceptable salt, or its solvate:

[0024] ;

[0025] where R 1 are independently methyl (Me-) or difluoromethyl (CF 2 H-);

[0026] R 2 is independently H, Me or Et;

[0027] R 3 is independently H, MeO or Cl;

[0028] C n h 2n+2 is an alkyl group, n≥2;

[0029] is a substituted benzene ring or pyridine ring;

[0030] X is C or N;

[0031] Y is C or N.

[0032] The C n h 2n+2 is ethyl, n-propyl, isopropyl, n-butyl or n-octyl.

[0033] said for , , , or .

[0034] Inhibitor compounds of the present invention are specifically shown in the following table:

[0035]

[0036] R in formula I and formula II 1 is an independent ...

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Abstract

The invention discloses novel 3-cyclopropylmethoxy-4-alkoxybenzamide PDE (phosphodiesterase) 4 inhibitors. The inhibitors are compounds represented in a general formula I or a general formula II, prodrugs thereof, pharmaceutically usable salts thereof or solvates thereof, wherein R<1> is independent methyl (Me-) or difluoromethyl (CF2H-); R<2> is independent H, Me or Et; R<3> is independent H, MeO or Cl; CnH(2n+2) is alkyl, and N is larger than or equal to 2; a substance shown in the specification is a substituted benzene ring or pyridine ring; X is C or N; Y is C or N. The novel 3-cyclopropylmethoxy-4-alkoxybenzamide PDE 4 inhibitors have the advantages of high in-vitro enzyme inhibition activity, capability of selective application to PDE4 and good anti-inflammation effect and anti-depression effect.

Description

technical field [0001] The invention relates to the technical field of catechol formamide derivatives, in particular to novel 3-cyclopropylmethoxy-4-alkoxybenzamide phosphodiesterase 4 inhibitors. Background technique [0002] Depression is a stress-induced affective disorder with a high incidence, and its mechanism has not been fully elucidated so far. Factors such as lack of monoamine neurotransmitters in the brain, negative feedback disorder of the hypothalamus-pituitary-adrenal axis, and low neurotrophic and plasticity closely related to the occurrence of depression. A large amount of evidence has confirmed that patients with depression are often accompanied by a certain degree of cognitive dysfunction, mainly manifested as inattention, memory loss, and slow thinking. More and more evidence shows that cognitive impairment in patients with depression represents an important functional impairment, which can easily induce Alzheimer's disease. high risk of recurrence. How...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C235/46C07C235/56C07D213/75A61P29/00A61P25/24
CPCC07C235/46C07C235/56C07D213/75
Inventor 徐江平周中振程玉芳
Owner 兰晟生物医药(苏州)有限公司
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