CN110003157A - A kind of novel flavone compound and its application with angst resistance effect - Google Patents
A kind of novel flavone compound and its application with angst resistance effect Download PDFInfo
- Publication number
- CN110003157A CN110003157A CN201910291600.0A CN201910291600A CN110003157A CN 110003157 A CN110003157 A CN 110003157A CN 201910291600 A CN201910291600 A CN 201910291600A CN 110003157 A CN110003157 A CN 110003157A
- Authority
- CN
- China
- Prior art keywords
- mouse
- group
- compound
- arch
- resistance effect
- 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.)
- Pending
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A kind of novel flavone compound and its application with angst resistance effect, the chemical structure of the present invention provides a kind of novel flavone compound with angst resistance effect.The bulk pharmaceutical chemicals with antianxiety related drugs that may be used as preparing various dosage forms, for treating and the medical usage of anxiety-related disorder.
Description
Technical field
The invention belongs to field of medicinal chemistry, specifically, the present invention describes the novel flavones with angst resistance effect
The chemical structure of class compound.In addition, the present invention also describes the anti-oxidant and antifatigue effect and purposes of this kind of compound
Deng.
Background technique
Anxiety is one of the most common type emotional state, but if the severity of anxiety and objective event or situation are obviously not
When symbol or duration are too long, pathological anxiety, referred to as anxiety symptom are reformed into, by correct check-up, has as a result been accorded with
Dependent diagnostic standard is closed, anxiety disorder can be diagnosed as.Anxiety disorder (anxiety neurosis) is also known as anxiety neurosis, is one
Kind by lasting sexual tension, worry, fear or it is ictal in terror characterized by emotional handicap.Be presented without firm basisization also without
The mood on tenterhooks and frightened and restless for specifying objective objects and concrete idea content, be also accompanied by vegetative nerve symptom and
Muscular tone and motility uneasiness etc. are common a major class phrenoblabia and public health problem.Anxiety disorder can be divided into frightened
Probably two kinds of forms of obstacle and generalized anxiety disorder.Latest survey the results show that anxiety disorder affects the population in the U.S. about 17.2%,
It is external separately some researches show that, exist in losing eye patient in severe anxiety be up to 54%.In China, anxiety disorder has become modern society
The common disease and frequently-occurring disease of meeting, affect people's lives quality.Anxiety disorder and mood regulation, physical and mental health are closely related, early
The theory of traditional Chinese medical science of phase is to contain the original thought of mood regulation.
Studies have shown that anxiety disorder be it is a kind of due in human body 14 kinds of neurotransmitter-dysregulations lead to the psychiatric of emotional handicap
Disease, scientist's discovery, we are in vivo in existing 14 kinds of neurotransmitters, the rising of NE can allow people generate it is anxious, uncomfortable in chest,
Situations such as heart pain, cardiovascular dysfunction, expiratory dyspnea；People can be easy to give free rein to fancy if NPY is unbalance；5-HT is unbalance, people
It then persistently falls into the case where can'ting be happy but also feel restless not only；γ-aminobutyric acid is unbalance, and people can feel is vexed, is vexed etc..
Other 10 kinds of neurotransmitters are unbalance, and the corresponding anxiety disorder symptom of the mediator can also occur therewith in people.Conversely, NE adjustment balance, burnt
Consider uneasy disappear；DA is normal, then no longer associates, and somatization is improved；5-HT balance, it is known that happiness, anger, grief and joy, no longer day and night
Hardly possible peace；γ-aminobutyric acid balance, people is no longer especially sensitive to the external world, no longer doubles because of its slight change with regard to Anxiety；ACH is flat
Weighing apparatus is vexed, vexed can disappear.
Existing widely used anxiolytic drugs has certain defect to be difficult to meet clinical demand.Previously anxiety disorder is sent out
The research of sick biomechanism is concentrated mainly on serotonin (5-HT), γ-aminobutyric acid (GABA) and norepinephrine (NE)
Mediator access, benzene phenodiazine with this correspondingIt class and selective serotonin reuptake inhibitor (SSRI), serotonin and goes
The drugs such as methylepinephrine reuptaking inhibitor (SNRIs) class are widely used to the clinical treatment [3] of anxiety disorder.However,
There are the adverse reactions such as excess sedation, gastrointestinal reaction, dysautonomia and sex dysfunction for existing drug, treat nothing
Effective solution is not yet received in the problem of recurring again after effect or treatment.Therefore, it is more preferable to find therapeutic effect, highly-safe, pair is made
It is extremely urgent with less anxiolytic drugs.
Natural flavonoid compound is that one kind is widely present in nature, the natural polyphenol class with multiple pharmacological activity
Close object.A large number of studies show that flavone compound has antiviral, antioxidant activity, antitumor, anti-osteoporosis, anti-inflammatory, anti-
The bioactivity such as depression, anticancer.Hitherto it is found that a variety of flavone compounds have angst resistance effect, such as Wolfman C leads to
Cross 2 kinds of rat behaviors experimental studies have found that, 1mgkg-1Chrysin can be dramatically increased in elevated plus-maze test greatly
Mouse enters the times and duration of open arms, while 3mgkg-1Chrysin hole plate experiment can increase rat exploratory heading number and
Time.Show that Chrysin has angst resistance effect.Apiolin dosage is 3mgkg-1When mouse elevated plus-maze experiment in
Increase mouse and enter open arms times and duration, shows apparent angst resistance effect.Isholal O etc. is overhead using mouse
Plus maze tests and makees pre-treatment, the experiment of hole plate and the experiment of light and shade case with Flumazenil (ionic GABA receptor antagonist) and comments
Valence amentoflavone DE Antianxiety Activity, shows to effectively increase exploratory heading frequency, time in open arms and enters camera-lucida
Time, have significant Antianxiety Activity.
Chalcone is the flavone compound containing 1,3- diphenylprop enone structure in molecule.It is distributed widely in more
It plants in the root, stem and leaf of Chinese medicine.It can be a kind of important in conjunction with a variety of receptors since its molecular structure has larger flexibility
Organic medicinal intermediate shows extensive bioactivity.Chalcone compounds show tempting development prospect, in recent years
Come extremely active to the research in terms of its bioactivity.
Since chalcone compounds have special molecular structure and extensive bioactivity, repaired by various structures
Decorations change the physicochemical property and pharmacological activity of compound, such as modify the ketenes chain for connecting A, B ring in chalcone structure
Deng, especially reducing toxic side effect, improving selectivity, improve water solubility etc. play the role of it is good.The present inventor's warp
Cross long-term and arduous research experiment, design, synthesize it is final obtained a series of new chalcone compounds, and through pharmacological activity
Detection finds that they have good antianxiety and anti-oxidant isoreactivity.With the continuous depth studied chalcone compounds
Enter, more chalcones new drugs will be developed is used for clinic and promote the well-being of mankind.
Summary of the invention
The technical problem to be solved in the present invention is to provide new antianxiety type of compounds and its drugs.Specifically, this
Invention provides formula (C37) compound represented or its pharmaceutically acceptable salt:
Compound (C37) are as follows:
(E)-1-[3-(Dimethylamino)phenyl]-3-[2-methoxy-5-(3-methylbut-3-en-2-
yl)-4-(tetra-hydro-2H-pyran-2-yloxy)phenyl]prop-2-en-1-one
(E) -1- [3- (diethylin) phenyl] -3- [2- methoxyl group -5- (3- methyl -3- butene-2 base) -4- (tetrahydro pyrrole
Mutter -2- oxygroup) phenyl] -2- acrylic -1- ketone
1H NMR (CDCl3,300MHz): δ 7.76 (d, 1H, J=15.6Hz, H β), 7.43 (s, 1H, H2'), 7.38 (d,
1H, J=15.6Hz, H α), 7.29-7.33 (m, 2H, H5', H6'), 6.95 (t, 1H, J=2.4Hz, H4'), 6.93 (s, 1H,
), H6 6.85 (s, 1H, H3), 5.51 (s, 1H, THP), 5.11 [s, 1H, ArCH (CH3) C (CH3) CH2], 5.06 [d, 1H, J=
0.6Hz, ArCH (CH3) C (CH3) CH2], 3.63 (q, 1H, J=6.9Hz, ArCH (CH3) C (CH3) CH2], 3.59-3.89 (m,
2H,THP-2H),3.01[s,6H,N(CH3)2],1.68[s,3H,ArCH(CH3)C(CH3)CH2],1.55-2.11(m,6H,
), THP 1.46 [d, 3H, J=6.9Hz, ArCH (CH3) C (CH3) CH2]
An object of the present invention is to provide a kind of novel flavone compound with angst resistance effect.
The second object of the present invention is to provide a kind of preparation method of novel chromocor compound.
In the present invention, we use and have been chemically synthesized a kind of novel flavone compound C37.Utilize mouse
The measurement of Behaviors survey and Monoamines content, it was demonstrated that C37 has apparent angst resistance effect (details are shown in embodiment 1).Benefit
It is tested with mice burden swimming, the antifatigue effect of the verifying C37 on whole animal level can be obviously prolonged mouse weight bearing
Swimming time (details are shown in embodiment 2).Utilize the anti-oxidant experiment of drosophila, it was demonstrated that C37 significantly extends life span of drosophila melanogaster and alleviates sub- anxious
Property oxidative injury (details are shown in embodiment 3).
Detailed description of the invention:
Compound recited herein is intended merely to that the compound of the present invention classification and structure type is better described, not
The limitation present invention.
Fig. 1 illustrates the compound structure of the compound C37 of synthesis.
Specific embodiment
The experiment of 1 C37 angst resistance effect
1.1 Elevated plus-maze
Sample: C37
Experimental animal: healthy mice
Experimental method:
Take mouse 45, blank control group and C37 high and low dose group, every group 15.Control group is early daily through stomach-filling approach
8 points are given 1% carboxymethylcellulose sodium solution (0.2mL/10g weight), and C37 is given in C37 high and low dose group stomach-filling daily
(15mg/kg and 5mg/kg, 0.2mL/10g weight), successive administration 7 days.When experiment, mouse is put in dim light, surrounding is with black
On the Elevated plus-maze of color screen.Mouse acquires 5min video towards the placement of wall end is opened back to experimenter, head.Every mouse
It all must first be wiped with low-concentration ethanol after finishing experiment, then be wiped with alcohol in high concentration；After equal alcohol volatilization, according to above-mentioned step
Suddenly, it is further continued for putting the 2nd mouse, until all animals all finish experiment.Video is watched, record mouse enters open arms number and stagnant
The time is stayed, is closed arm number and residence time, open arms number ratio and residence time ratio are calculated.
Open arms number ratio=open arms number/(open arms number+close arm number)
Open arms time scale=open arms residence time/(the open arms residence time+close the arm residence time)
Statistical procedures:
Experimental data is handled using SPSS17.0 statistical software, is as a result usedIt indicates, one-way analysis of variance method
Data processing is carried out, LSD method is compared two-by-two, and P < 0.05 is statistically significant.
Experimental result:
By table 1-1 it is found that compared with the control group, the entrance open arms time scale and open arms number of C37 high dose group rat
Ratio obviously increases, and has significant difference (P < 0.01).
Table 1-1 C37 to sleep-deprived rat anxiety-like behavior influence (N=10)
Note: compared with blank control group,**P<0.01。
The experiment of 1.2 light and shade casees
Laboratory sample: C37
Experimental animal: mouse
Experimental method:
Mouse is divided into 5 groups, every group 15: blank group, that is, physiological saline group, C37 low dose group 5mg/kg, high dose group
15.0mg/kg and diazepam (DZP) positive controls 2.0mg/kg.Administration: 1 time a day, continuous 7d gastric infusion is each in 7d
After administration group stomach-filling 5h, Behavior test is carried out in 8:00-14:00.When experiment starts, mouse is placed in animal box, is allowed to
Freely explore 5min.Mouse is put into camera-lucida by experiment when starting, and mouse head unclamps it is allowed freely to explore rapidly towards camera bellows
5min, and record mouse and enter the number of camera-lucida and in the camera-lucida movable time.
Statistical procedures: the same
Experimental result:
By 1-2 it is found that compared to the blank group, C37 high dose group (15.0g/kg) and diazepam group can dramatically increase small
Mouse movable time (P < 0.05) in camera-lucida, without significant difference between other each groups.Compared to the blank group, diazepam group and C37
High dose group can increase number of activities (P < 0.05) of the mouse in camera-lucida.
Influence that table 1-2 C37 tests mouse LDB (N=15)
Note: compared with blank control group,*P < 0.05,**P<0.01。
1.3 bury pearl experiment
Laboratory sample: C37
Experimental animal: mouse
Experimental method:
Mouse is divided into 5 groups, every group 15: control group, that is, physiological saline group, C37 low dose group 5mg/kg, high dose group
15.0mg/kg and positive (DZP) the control group 2.0mg/kg of diazepam.Administration: 1 time a day, continuous 7d gastric infusion is each in 7d
After administration group stomach-filling 5h, Behavior test is carried out in 8:00-14:00.
When experiment starts, mouse is placed in the big box for being placed with glass marbles.It is allowed to freely explore 30min.Wait test
Terminate, counts hoodle and bury quantity, glass marbles are considered as burial to bury 2/3 or more.Referred to burying hoodle quantity as observation
Mark.
Statistical procedures: the same
Experimental result:
By table 1-3 it is found that compared with the control group, the quantity that mouse buries hoodle can be significantly reduced in C37 middle dose group,
C37 high dose group and diazepam group it is extremely significant inhibit mouse bury hoodle quantity.Illustrate that C37 can significant skilful mouse processed
The behavior without aggressive foreign matter of burying has angst resistance effect.
Table 1-3 C37 to mouse bury pearl experiment influence (N=15)
Note: compared with blank control group,*P < 0.05,**P<0.01。
Influence of 1.4 C37 to mouse mouse hippocampal tissue Glutamic Acid, alpha-aminobutyric acid content
After Elevated plus-maze Behavior test, Normal group, model group, diazepam group and C37 middle dose group mouse
Anesthesia immediately puts to death, breaks end, and removes Rat hippocampus on Yu Bingtai, hippocampal tissue is equally divided into two halves, half hippocampus group
It is woven under condition of ice bath, claims quality, glass homogenizer homogenization；0.4mol/L perchloric acid solution 1ml, refrigerated centrifuge (4 is added
DEG C), 12000r/min is centrifuged 10min, and supernatant is taken to be centrifuged with condition 2 times, and 0.4mol/L perchloric acid solution is settled to 1ml, and -80
DEG C save.Derivative reaction before sample column: taking 10 μ l of supernatant, and 40 μ l OPA derivative reagents are added, and vortex 30s stands 1min,
20 μ l of sample introduction.It is quantitative using High Performance Liquid Chromatography with Fluorescence Detection.
Statistical procedures: the same
Experimental result:
By table 1-4 it is found that the expression quantity of model group rats hippocampal tissue Glutamic Acid significantly rises compared with Normal group,
The expression quantity of γ-aminobutyric acid is decreased obviously；Diazepam is compared with C37 high dose group is with model group, paddy in Rat hippocampus
The expression quantity of propylhomoserin significantly reduces and the expression quantity of γ-aminobutyric acid significantly improves, C37 middle dose group compared with diazepam group,
Difference is not significant.
Influence of the table 1-4 C37 to Rat hippocampus Glutamic Acid, alpha-aminobutyric acid content
Note: * is compared with Normal group, P < 0.05；△Compared with model group, P < 0.05
The experiment of 2 C37 antifatigue effects
Animal is grouped at random, and every group 15.C37 is low, high dose concentration is followed successively by 5,15mg/kg, and control group gives physiology
Salt water, by the daily stomach-filling of 0.2mL/10g 1 time, continuous 10d.At the 11st day, mice burden swimming experiment is carried out, with own body weight
6% sheet lead is bundled in mouse root of the tail, sets 25 DEG C of water went swimmings, and record mouse starts swimming to the death time.If dosage group is small
Mouse swimming time is considerably longer than control group, then it is believed that mice burden swimming ability can be enhanced in the sample.Experimental data withIt indicates, one-way analysis of variance is carried out using SPSS17.0 statistical software.
Statistical procedures: the same
Experimental result:
By table 2-1 it is found that compared with the control group, each administration group of C37 can be obviously prolonged the mice burden swimming time, and
Difference is statistically significant (P < 0.01, P < 0.05).The result shows that under this experiment condition, C37 can enhance the negative of mouse
Weight Burden-Swimming Ability of KM.
Table 2-1 C37 to mouse swimming time influence (N=15)
Note: * * compared with the control group, P < 0.01；* compared with the control group, P < 0.05
3 C37 test the subacute oxidative damage of drosophila
30 age in days drosophilas are taken, every group of male and female each 100, give the H containing 20% respectively2O26% glucose solution, every 5
Hour record is primary, until drosophila is all dead.
Statistical procedures: the same
Experimental result
In the experiment of subacute oxidative damage, pole is presented in high dose group male and female mean survival time compared with blank control group
Significant difference (P < 0.01)；There was no significant difference for low dose group.
Effect (n=100) of the table 3-1 C37 to the subacute oxidative damage of drosophila
Note: * * compared with the control group, P < 0.01；* compared with the control group, P < 0.05
Conclusion:
C37 can obviously increase the entrance open arms number and time scale of mouse, increase time of the mouse in camera-lucida and
Number of activities in camera-lucida, it is significant that mouse is inhibited to bury the behavior without aggressive foreign matter, hippocampal tissue Glutamic Acid can be changed
And the content of γ-aminobutyric acid, thus it is speculated that it may play angst resistance effect by the synthesis and release for inhibiting monoamine transmitters.It is negative
Weight swimming test is the animal model for evaluating drug antifatigue effect, the experimental results showed that, C37 can be obviously prolonged the swimming of rat
The time is exhausted to power, there is good antifatigue effect.In addition, C37 can significantly extend drosophila in subacute oxidative damage experiment
Mean survival time.
In conclusion chalcone compounds C37 antianxiety, it is antifatigue and in terms of embody clear superiority.
Claims (5)
1. compound and its officinal salt with the following chemical structure:
Compound (C37) are as follows:
(E)-1-[3-(Dimethylamino)phenyl]-3-[2-methoxy-5-(3-methylbut-3-en-2-yl)-4-
(tetra-hydro-2H-pyran-2-yloxy)phenyl]prop-2-en-1-one
(E) -1- [3- (diethylin) phenyl] -3- [2- methoxyl group -5- (3- methyl -3- butene-2 base) -4- (oxinane -2-
Oxygroup) phenyl] -2- acrylic -1- ketone
1H NMR (CDCl3,300MHz): δ 7.76 (d, 1H, J=15.6Hz, H β), 7.43 (s, 1H, H2'), 7.38 (d, 1H, J
=15.6Hz, H α), 7.29-7.33 (m, 2H, H5', H6'), 6.95 (t, 1H, J=2.4Hz, H4'), 6.93 (s, 1H, H6),
6.85 (s, 1H, H3), 5.51 (s, 1H, THP), 5.11 [s, 1H, ArCH (CH3) C (CH3) CH2], 5.06 [d, 1H, J=
0.6Hz, ArCH (CH3) C (CH3) CH2], 3.63 (q, 1H, J=6.9Hz, ArCH (CH3) C (CH3) CH2], 3.59-3.89 (m,
2H,THP-2H),3.01[s,6H,N(CH3)2],1.68[s,3H,ArCH(CH3)C(CH3)CH2],1.55-2.11(m,6H,
), THP 1.46 [d, 3H, J=6.9Hz, ArCH (CH3) C (CH3) CH2]
2. preceding claim compound is used for the relevant disease of antianxiety function.
3. being used for the pharmaceutical composition of the relevant disease of antianxiety function comprising compound described in claim 1 and pharmacy
Upper acceptable carrier.
4. pharmaceutical composition as claimed in claim 3 is made into tablet, capsule, oral solution, injection, pulvis, paste or outer
Use medical fluid.
5. application of the compound described in claim 1 in the drug that preparation is used for the relevant disease of antianxiety function.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910291600.0A CN110003157A (en) | 2019-04-12 | 2019-04-12 | A kind of novel flavone compound and its application with angst resistance effect |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910291600.0A CN110003157A (en) | 2019-04-12 | 2019-04-12 | A kind of novel flavone compound and its application with angst resistance effect |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN110003157A true CN110003157A (en) | 2019-07-12 |
Family
ID=67171252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910291600.0A Pending CN110003157A (en) | 2019-04-12 | 2019-04-12 | A kind of novel flavone compound and its application with angst resistance effect |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110003157A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113398129A (en) * | 2021-08-10 | 2021-09-17 | 河北中医学院 | Application of trichophyton A in preparation of anxiolytic drugs |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1475487A (en) * | 2003-07-09 | 2004-02-18 | 东华大学 | Fluoro flavon containing compound, manufacturing method and its use |
| CN1475488A (en) * | 2003-07-09 | 2004-02-18 | 东华大学 | Fluoro isoflavone containing derivative, monufacturing method and its use |
| CN102697770A (en) * | 2012-06-13 | 2012-10-03 | 长春瑞德医药科技有限公司 | Murraya paniculata leaf and application of mono compound in preparation of sedative and hypnotic drugs |
| US20140096780A1 (en) * | 2012-10-09 | 2014-04-10 | R.J. Reynolds Tobacco Company | Tobacco-derived composition |
| CN109503351A (en) * | 2018-11-30 | 2019-03-22 | 温州医科大学 | A kind of chalcone derivative containing allylic structure and its application |
-
2019
- 2019-04-12 CN CN201910291600.0A patent/CN110003157A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1475487A (en) * | 2003-07-09 | 2004-02-18 | 东华大学 | Fluoro flavon containing compound, manufacturing method and its use |
| CN1475488A (en) * | 2003-07-09 | 2004-02-18 | 东华大学 | Fluoro isoflavone containing derivative, monufacturing method and its use |
| CN102697770A (en) * | 2012-06-13 | 2012-10-03 | 长春瑞德医药科技有限公司 | Murraya paniculata leaf and application of mono compound in preparation of sedative and hypnotic drugs |
| US20140096780A1 (en) * | 2012-10-09 | 2014-04-10 | R.J. Reynolds Tobacco Company | Tobacco-derived composition |
| CN109503351A (en) * | 2018-11-30 | 2019-03-22 | 温州医科大学 | A kind of chalcone derivative containing allylic structure and its application |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113398129A (en) * | 2021-08-10 | 2021-09-17 | 河北中医学院 | Application of trichophyton A in preparation of anxiolytic drugs |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Nuckolls et al. | Tongue force and tongue motility are differently affected by unilateral vs bilateral nigrostriatal dopamine depletion in rats | |
| BR112019026916A2 (en) | cannabidiolic acid ester compositions and uses thereof | |
| CN1850836A (en) | Celosia argentea suponin compound and its pharmaceutical use | |
| ES2633127T3 (en) | Use of albiflorine to improve anxiety and sleep disorder | |
| CN1235541A (en) | Treatment of spasticity, convulsions by isovaleric acid derivatives CNS | |
| CN101590065A (en) | Siberia Radix Polygalae sugar A1, Siberia Radix Polygalae sugar A5 and the tenuifoliside A application in preparation treatment depression product | |
| CN1224383C (en) | Blood sugar reducing compound | |
| CN110003157A (en) | A kind of novel flavone compound and its application with angst resistance effect | |
| CN1638772A (en) | Anti-viral compounds | |
| JP4714304B2 (en) | Use of 5-methyl-1,3-benzenediol or its derivatives in the preparation of pharmaceuticals and functional foods for the treatment or prevention of depression | |
| CN1186336C (en) | Prepn and application in preparing medicine of fraxinus general coumarin | |
| KR100407399B1 (en) | Use of myricetin as an inhibitor for serotonin N-acetyltransferase | |
| Ilbäck et al. | Evaluation of cardiovascular effects of caffeine using telemetric monitoring in the conscious rat | |
| CN106727480A (en) | Applications of the Fex-3 in anti-obesity medicine is prepared | |
| CN109414507A (en) | For preventing and treating the high selectivity adenosine A 3 receptor subtype agonist of neurodegenerative disease | |
| CN102716120B (en) | Application of (3R)-des-O-methyl lasiodiplodin in preparation of drugs for preventing or treating depression | |
| KR20180053032A (en) | Novel piperidine derivatives and pharmaceutical composition comprising the same | |
| CN1277567C (en) | Medicinal composition for treating nervous system disease and its preparation method | |
| CN104224796B (en) | Application of oleanane triterpene ester derivative in preparation for anti-neurodegeneration medicine | |
| CN105878258B (en) | Purposes of the acteoside in preparing antidepressant | |
| CN105832724A (en) | Use of indolol in preparation of anti-depression drugs | |
| KR20210097487A (en) | Composition for preventing, improving or treating sleep disorders comprising fucoidan | |
| CN100441589C (en) | Puerarin compound containing water soluble group and its preparation and use | |
| CN109464433B (en) | Application of kaurenoic acid in preparation of anti-depression drugs | |
| JP2019097566A (en) | Composition for regulating biological clock |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| WD01 | Invention patent application deemed withdrawn after publication |
Application publication date: 20190712 |
|
| WD01 | Invention patent application deemed withdrawn after publication |