CN106146297A - A kind of new compound and application thereof - Google Patents
A kind of new compound and application thereof Download PDFInfo
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- CN106146297A CN106146297A CN201510155684.7A CN201510155684A CN106146297A CN 106146297 A CN106146297 A CN 106146297A CN 201510155684 A CN201510155684 A CN 201510155684A CN 106146297 A CN106146297 A CN 106146297A
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- compound
- pentanediol
- benzoic acid
- metal ion
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- 0 *C([C@@](C=CC(*)=C)N)O Chemical compound *C([C@@](C=CC(*)=C)N)O 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/64—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring the carbon skeleton being further substituted by singly-bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
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- Chemical & Material Sciences (AREA)
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- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The present invention relates to a kind of new compound and application thereof, more particularly to 2-(1,4-pentanediol) benzoic acid derivative and salt thereof, and this compounds is in preparation prevention and the treatment heart, cerebral ischemia diseases, the application that prevents and treat in brain dementia medicine.
Description
Technical field
The present invention relates to a kind of new compound and application thereof, be specifically related to 2-(1,4-pentanediol) benzoic acid derivative and
Its salt, and this compounds is in preparation prevention and the treatment heart, cerebral ischemia diseases, the application that prevents and treat in brain dementia medicine
Background technology
Cerebral ischemia disease has the features such as sickness rate height, disability rate and mortality rate are big, is that the commonly encountered diseases of harm human life's health is with many
Morbidity, therefore finds ischemia resisting medicine and causes the extensive concern of Chinese scholars.
Butyphthalide has another name called Butylphthalide, is originally found in celery seed, and its pharmacodynamics feature covers a lot of aspect effect: 1, energy
Improve cerebral ischemia-reperfusion energy metabolism；2, it is obviously reduced focal cerebral ischemia in rats cerebral infarct size, improves neurological deficit；3, improve
The cerebral edema that local cerebral ischemia causes；4, ischemic region local cerebral blood flow and soft bus wire are significantly improved；5, energy
Significantly improve the dysmnesia that local cerebral ischemia causes.
There is the launch such as butyphthalide soft capsule, butyphthalide sodium chloride injection.Indication is light for treatment, in
Degree acute ischemic cerebral apoplexy.
Document report (research " Acta Pharmaceutica Sinica " 1997,32 (9) of Wang Chunhua etc.: butylphthalide metabolite in rats:
641-646), butyphthalide main metabolites in vivo is 3-(3 '-hydroxybutyl) isobenzofuran-(3H)-one.
In urine, butyphthalide original shape is about the ratio of 9:91, cerebral tissue mesarcs medicine and metabolite about with the ratio of metabolite
For 44:56, but the metabolite in brain only has 3-(3 '-hydroxybutyl) isobenzofuran-(3H)-one.
The structural formula of 3-(3 '-hydroxybutyl) isobenzofuran-(3H)-one is as follows:
During carrying out noval chemical compound Pharmacological Activity Screening, the present inventor is to 3-(3 '-hydroxybutyl) isobenzofuran-(3
H)-one hydrolyzate 2-(1,4-pentanediol) benzoic acid carries out structure of modification, prepares a series of 2-(1,4-pentanediol)
Benzoic acid derivative noval chemical compound, beat all, these 2-(1,4-pentanediol) benzoic acid derivative and salt thereof have very
Excellent cardiovascular and cerebrovascular activity.Because containing chiral carbon atom in this compounds, therefore this compounds be racemoid or
Its optically active compound, its general structure is as follows:
Formula 2:2-(1,4-pentanediol) benzoic acid derivative
Wherein R is halogen atom or hydroxyl or methoxyl group or nitro or amino or alkyl or amide or carboxyl.
The salt of formula 3:2-(1,4-pentanediol) benzoic acid derivative
Wherein R is halogen atom or hydroxyl or methoxyl group or nitro or amino or alkyl or amide or carboxyl；
Wherein n=1 or 2 or 3, M are monovalent metallic ion, bivalent metal ion, trivalent metal ion or organic base.
Summary of the invention
The purpose of the present invention, it is simply that provide a kind of new compound and application thereof, specifically refers to 2-(1,4-pentanediol) benzene first
Acid derivative and salt thereof, and this compounds is at preparation prevention and the treatment heart, cerebral ischemia diseases；Prevention and treatment brain dementia
Application in medicine.
In order to complete the purpose of the present invention, the present inventor prepares and have studied 2-(1,4-pentanediol) benzoic acid and derives
Thing and salt thereof, find through zoopery, and 2-(1,4-pentanediol) benzoic acid derivative and salt thereof move at cerebral ischemia diseases
In thing experiment, effect is notable.
Prior art has no the report to such noval chemical compound.
2-(1,4-pentanediol) benzoic acid derivative compound, because containing chiral carbon atom, therefore such chemical combination in compound
Thing is racemoid or its optically active compound, and its general structure is as follows:
Wherein R is halogen atom, hydroxyl, methoxyl group, nitro, amino, alkyl, amide or carboxyl.
The present invention also provides for the salt of 2-(1,4-pentanediol) benzoic acid derivative, because containing chiral carbon atom in compound,
Therefore this compounds is racemoid or its optically active compound, and its general structure is as follows:
Wherein R is halogen atom or hydroxyl or methoxyl group or nitro or amino or alkyl or amide or carboxyl；
Wherein n=1 or 2 or 3, M are monovalent metallic ion, bivalent metal ion, trivalent metal ion or organic base.
Further illustrating as the present invention, described M is monovalent metallic ion lithium, sodium, potassium, or bivalent metal ion magnesium, calcium,
Zinc, ferrum, or trivalent metal ion ferrum, aluminum；Or organic base N, N '-dibenzyl-ethylenediamin, aniline, benzene methanamine, benzylamine, diformazan
Amine, diethylamine, morpholine, meglumine, trimethylamine, triethylamine, tert-butylamine or other organic bases.
2-of the present invention (1,4-pentanediol) benzoic acid derivative is preferably halo 2-(1,4-pentanediol) benzoic acid.Because chemical combination
Containing chiral carbon atom in thing, therefore this compound is racemoid or its optically active compound, and its general structure is as follows:
Wherein R is halogen atom.
The salt of 2-of the present invention (1,4-pentanediol) benzoic acid derivative is preferably halo 2-(1,4-pentanediol) benzoic acid and derives
The salt of thing.Because containing chiral carbon atom in compound, therefore this compound is racemoid or its optically active compound,
Its general structure is as follows:
Wherein R is halogen atom.
Wherein n=1 or 2 or 3, M are monovalent metallic ion, bivalent metal ion, trivalent metal ion or organic base.As
Further illustrating, described M is monovalent metallic ion lithium, sodium, potassium, or bivalent metal ion magnesium, calcium, zinc, ferrum, or trivalent gold
Belong to ionic iron, aluminum；Or organic base N, N '-dibenzyl-ethylenediamin, aniline, benzene methanamine, benzylamine, dimethylamine, diethylamine, morpholine,
Meglumine, trimethylamine, triethylamine, tert-butylamine or other organic bases.
The compounds of this invention can be prepared as follows:
The preparation of 2-(1,4-pentanediol) benzoic acid derivative:
Wherein R is halogen atom or hydroxyl or methoxyl group or nitro or amino or alkyl or amide or carboxyl.
The preparation of 2-(1,4-pentanediol) benzoic acid derivative potassium salt:
Wherein R is halogen atom or hydroxyl or methoxyl group or nitro or amino or alkyl or amide or carboxyl.
The preparation of 2-(1,4-pentanediol) benzoic acid derivative aniline salt:
Wherein R is halogen atom or hydroxyl or methoxyl group or nitro or amino or alkyl or amide or carboxyl；
2-(1,4-pentanediol) benzoic acid N, the preparation of N '-dibenzyl ethylenediamine salt:
Wherein R is halogen atom or hydroxyl or methoxyl group or nitro or amino or alkyl or amide or carboxyl；
Instantiation:
The preparation of chloro 2-(1,4-pentanediol) benzoic acid derivative (code name W1):
The preparation of chloro 2-(1,4-pentanediol) benzoic acid derivative potassium salt (code name W1a):
The preparation of chloro 2-(1,4-pentanediol) benzoic acid derivative aniline salt (code name W1b):
Chloro 2-(1,4-pentanediol) benzoic acid N, the preparation of N '-dibenzyl ethylenediamine salt (code name W1c):
The present invention also provides for 2-(1,4-pentanediol) benzoic acid derivative and salt thereof in preparation prevention and the treatment heart, cerebral ischemia disease
Application sick, that prevent and treat in brain dementia medicine.
Detailed description of the invention
The present invention is described in further detail the most by way of example, provides the implementation detail of the present invention, but should not
It it is considered as limitation of the present invention.
Embodiment 1: to Middle cerebral artery thrombosis model (Middle Cerebral Artery Thrombosis, MCAT)
Rat symptom and the impact of Range of Cerebral Infarction.
One, animal
SD rat, male and female half and half, body weight 190～250g.
Two, medicine and reagent
By reagent
W1、W1a、W1b、W1c。
Reagent
FeCl3*6H20 (A.R.), prepares with 1mol/L hydrochloric acid；Red tetrazolium (TTC), (C.P.).
Three, instrument
XTT stero microscope；Water bath with thermostatic control agitator；Electronic analytical balance.
Four, test method and result
(1) impact on MCAT rat symptom
1, packet is shown in Table 1
Table 1
2, be administered: before modeling prevention be administered, every day gastric infusion 1 time, successive administration 3 days, modeling in the 4th day, after modeling at once
Gavage gives one day dosage.After modeling 12 hours again gavage give one day dosage, matched group gives equivalent solvent.
3, modeling operation is implemented: rats by intraperitoneal injection 12% chloral hydrate solution (350mg/kg) is anaesthetized.Rat Right lateral position is solid
Fixed, to make a curved incision at paropia and external auditory meatus line midpoint, be about 1.5cm, pinch off temporalis also cuts, and exposes temporal bone,
At the 1mm of mouth side, make the bone window of an a diameter of 2.5mm by dental burr at cheekbone and temporo squamosum joint, clear up residue, cruelly
Dew middle cerebral artery (between tractus olfactorius and inferior cerebral vein).Suction is had 50% ferric chloride solution (1mol/L salt
Acid) the small pieces quantitative filter paper of 10ul applies on this section of middle cerebral artery, and about 30miri takes off filter paper after blood vessel color blackening,
Use normal saline flushing local organization, layer-by-layer suture, steam again and raise.
4, behavioral value: different time points (6h, 24h) carries out behavior scoring to animal after surgery.(1) put forward rat-tail and leave ground
About one chi, observes forelimb flexing situation.As double forelimb symmetries stretch to ground, it is designated as 0 point；As offside forelimb of performing the operation occurs that shoulder is bent
The flexing of song, elbow flexing, shoulder inward turning or existing wrist elbow has again inward turning person, is designated as 1 point.(2) animal is placed on smooth ground,
Push away both shoulders respectively to side shifting, inspection resistance.As bilateral resistance is reciprocity and is designated as 0 point effectively；As when operation offside promotes
Drop in resistance person, is designated as 1 point.(3) animal two forelimb is put on a wire netting, observe the muscular tension of two forelimbs.Bilateral flesh is opened
Power equity and strong person are 0 point；Operation offside muscle of anterior limb tension force decline is designated as 1 point.(4) put forward rat-tail and leave ground about one chi,
Animal has ceaselessly to operation offside revolver, is designated as 1 point, is otherwise designated as 0 point.According to above scale, full marks are 4
Point, mark is the highest, and the behavior disorder of animal is the most serious.
Result shows, sham operated rats has no that dystropy changes, and hemiplegia sample symptom all occur in model group rats 6h, 24h after surgery
Mainly showing as the interior receipts of offside forelimb of performing the operation, take on inward turning, muscle of anterior limb tension force reduces, shoulder drag decline.Compared with model group, respectively
The nervous symptoms of administration group rat 24h after surgery all significantly improves, and has obvious dose-effect relationship.
(2) impact on MCAT rat cerebral infarction scope
After animal via last behavior scoring, broken end takes brain.Removing olfactory bulb, cerebellum and low brain stem, residue part is preced with below 4 DEG C
Shape is cut into 5.Rapidly brain sheet is placed in TTC dye liquor and (every 5ml dye liquor contains
4%TTC1.5ml, 1MK2HPO40.1ml), 37 DEG C of lucifuge temperature are incubated 30 minutes, further take out, are placed in 10% formaldehyde
Liquid keeps in Dark Place.After dyed, non-ischemic region is rose, and infarct is white.White tissues is carefully dug down and weighs, with
Blocking tissue's weight accounts for the percentage ratio of total brain weight as Range of Cerebral Infarction.
Result shows, postoperative 24h is in addition to sham operated rats is without focus of infarct, and model group and administration group rat all have stalk in various degree
Plug stove.Compared with model group, the cerebral tissue infarct symptoms that ischemic brain injury is caused by each administration group rat is significantly improved,
And have obvious dose-effect relationship.
Embodiment 2: rat is moved the thrombotic the present embodiment that affects of a venous bypass and selects:
One, animal
SD rat, male and female half and half, body weight 190～250g.
Two, medicine and reagent
By reagent
W1、W1a。
Three, instrument
AEG-220 type electronic analytical balance；Df-206 type air dry oven.
Four, test method and result
1, packet is shown in Table 2
Table 2
2, it is administered
Every day gastric infusion 1 time, successive administration 3 days, thrombus model group gives equivalent solvent.Last is i.e. performed the operation after being administered.
3, modeling method
Being anaesthetized by rats by intraperitoneal injection 10% chloral hydrate 0.35ml/100g, dorsal position is fixed, and operation separates right neck total
Tremulous pulse and left external jugular vein.No. 0 surgical thread of a long 8cm weighed in advance is put in the polyethylene tube stage casing of 10cm length,
Being full of with normal saline solution, two client links are about 3cm and are full of intubating of normal saline.Left external jugular vein is inserted in one end of this pipe
After, the other end inserts right common carotid artery.Blood flow in polyethylene tube from right carotid, then backflows into left external jugular vein,
Constitute loop blood flow.Herba Clinopodii in after 10min, rapid removal of thromboses weighs, and it is heavily wet weight of thrombus that this weight deducts silk thread weight, paper；
Putting into 60 DEG C of dry 24h in baking oven, removal of thromboses is weighed, and it is heavily thrombosis dry weight that this weight deducts silk thread weight, paper.
Result shows, compared with thrombus model group, wet weight of thrombus and the dry weight of each administration group rat all substantially reduce, and has substantially
Dose-effect relationship.
Test example 3: the impact on scopolamine cause dementia mice learning and memory behavior:
One, material
SPF level KM mice, male, 18-22 gram.
0.9% normal saline solution.
Two, packet is shown in Table 3
Table 3
Three, it is administered
Mice vein respectively gives said medicine, successive administration 14 days.0.9% normal saline is given under sham operated rats equal conditions.
Four, the impact on mice jumping response
Mice last is administered and carried out jumping response training 1 time first 2 day every day.During training, mice to be measured is put in diving tower instrument,
Adapt to environment 5min.Then being energized to bottom screen, record mice is little in jumping off time (latent time) of plateau and 5min
Mus is jumped off the number of times (phase errors number of resurveying) shocked by electricity by plateau.Can correctly escape when meeting electricity irritation with mice association to flat
It it is index on platform.After last administration 30min in addition to blank group lumbar injection 0.9% normal saline solution, remaining each group
Inject the scopolamine injection liquid of 5mg/kg respectively, formally test after 30min, record mice latent time and
Resurvey in 5min phase errors number.
Five, statistical method
Data processing data is carried out checking between variance analysis and group by SPSS11.5 statistical software.
Six, experimental result
Result shows, scopolamine model group is compared with blank group, and mice escape latency substantially shortens, and errors number is bright
Aobvious increase (P ＜ 0.01), illustrates that memory deficits in mice model is successfully established.Compared with model group, each dosed administration group incubation period
All having prolongation in various degree, errors number also significantly reduces, and is respectively provided with significant difference.
Test example 4: on study and the impact of memory behavior after Cerebral Ischemia-reperfusion in Mice:
One, material
SPF level KM mice, male, 18-22 gram.
0.9% normal saline.
Two, experimental technique
The making of Cerebral Ischemia-reperfusion in Mice damage model: ip in mice (lumbar injection) 4% chloral hydrate 0.4g/kg anaesthetizes,
Neck medisection skin, blunt separation bilateral common carotid arteries, wear " 4-0 " operation silk thread under bilateral common carotid arteries, suspention is to bilateral
Common carotid artery blood flow blocks completely, extracts silk thread out and make its blood flow Reperfu-sion after lh.Sham operated rats is worn silk thread down but is not suspended blocking-up in midair
Blood flow, also extracts silk thread out after 1h.The most all mice skin sutures, steam again and raise.
Three, packet is shown in Table 4
Table 4
Four, it is administered
Once a day, from the same day of performing the operation, continuous gastric infusion 21 days.0.9% physiology is given under sham operated rats equal conditions
Saline.
Five, the impact on mice jumping response
Mice last is administered first 2 days, and after being administered, 30min carries out jumping response training.During training, mice to be measured is put into jumping
In platform instrument, adapt to environment 5min.Then to bottom screen be energized, record mice jump off plateau time (latent time) and
In 5min, mice is jumped off the number of times (phase errors number of resurveying) shocked by electricity by plateau.With mice association meet electricity irritation time can be just
Really escaping to platform is index.Last is formally test after being administered 1h, resurveys the phase in record mice latent time and 5min
Errors number.
Six, statistical method
Data processing data is carried out checking between variance analysis and group by SPSS11.5 statistical software.
Seven, experimental result
Result shows, the indices of model group mice all has pole significant difference (P < 0.01) with sham operated rats, and this is described
Model success.Compared with model group, each dosed administration group group all has prolongation in various degree incubation period, and errors number the most substantially subtracts
Few, it is respectively provided with significant difference.
Claims (6)
1. a new compound, it is characterised in that described compound is 2-(1,4-pentanediol) benzoic acid derivative,
Described compound is racemoid or its optically active compound, and its general structure is as follows:
Wherein R is halogen atom, hydroxyl, methoxyl group, nitro, amino, alkyl, amide or carboxyl.
2. the salt of compound as claimed in claim 1, it is characterised in that the salt of described compound be racemoid or
Its optically active compound, its general structure is as follows:
Wherein R is halogen atom, hydroxyl, methoxyl group, nitro, amino, alkyl, amide or carboxyl；
N=1 or 2 or 3, M are monovalent metallic ion, bivalent metal ion, trivalent metal ion or organic base.
3. as described in claim 1 compound, it is characterised in that described compound be halo 2-(1,4-penta 2
Alcohol) benzoic acid, described compound is racemoid or its optically active compound, and its general structure is as follows:
Wherein R is halogen atom.
The most as stated in claim 2, this noval chemical compound is halo 2-(1,4-pentanediol) benzoate, it is characterised in that
This compound is racemoid or its optically active compound, and its general structure is as follows:
Wherein R is halogen atom,
Wherein n=1 or 2 or 3, M are monovalent metallic ion, bivalent metal ion, trivalent metal ion or organic base.
5. the salt of 2-as described in claim 2 or 4 (1,4-pentanediol) benzoic acid derivative, it is characterised in that institute
The M stated is monovalent metallic ion lithium, sodium, potassium, or bivalent metal ion magnesium, calcium, zinc, ferrum, or trivalent metal ion ferrum, aluminum,
Or organic base N, N '-dibenzyl-ethylenediamin, aniline, benzene methanamine, benzylamine, dimethylamine, diethylamine, morpholine, meglumine, trimethylamine,
Triethylamine, tert-butylamine.
6. 2-as claimed in claim 1 or 2 (1,4-pentanediol) benzoic acid derivative and salt thereof are in preparation prevention and treatment
The heart, cerebral ischemia diseases, the application that prevents and treat in brain dementia medicine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201510155684.7A CN106146297A (en) | 2015-04-03 | 2015-04-03 | A kind of new compound and application thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN201510155684.7A CN106146297A (en) | 2015-04-03 | 2015-04-03 | A kind of new compound and application thereof |
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Family
ID=57338344
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112898224A (en) * | 2019-12-04 | 2021-06-04 | 中国科学院上海药物研究所 | Allyl alcohol-supported macrolide compound and application thereof |
Citations (4)
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|---|---|---|---|---|
| CN1382682A (en) * | 2002-05-09 | 2002-12-04 | 中国医学科学院药物研究所 | 2-(alpha-hydroxypentyl) benzoate and its preparing process and usage |
| CN101054346A (en) * | 2006-04-13 | 2007-10-17 | 温建波 | Preparation method and use for a set of novel compound and composition thereof |
| CN101402565A (en) * | 2008-11-14 | 2009-04-08 | 郑州大学 | Halogenated 2-(a-hydroxyl pentyl) benzoate, production method and uses thereof |
| CN103356521A (en) * | 2012-04-01 | 2013-10-23 | 石药集团恩必普药业有限公司 | Application of butylphthalide or derivatives thereof in preparation of medicaments for treating or preventing radiation brain damage |
-
2015
- 2015-04-03 CN CN201510155684.7A patent/CN106146297A/en active Pending
Patent Citations (4)
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|---|---|---|---|---|
| CN1382682A (en) * | 2002-05-09 | 2002-12-04 | 中国医学科学院药物研究所 | 2-(alpha-hydroxypentyl) benzoate and its preparing process and usage |
| CN101054346A (en) * | 2006-04-13 | 2007-10-17 | 温建波 | Preparation method and use for a set of novel compound and composition thereof |
| CN101402565A (en) * | 2008-11-14 | 2009-04-08 | 郑州大学 | Halogenated 2-(a-hydroxyl pentyl) benzoate, production method and uses thereof |
| CN103356521A (en) * | 2012-04-01 | 2013-10-23 | 石药集团恩必普药业有限公司 | Application of butylphthalide or derivatives thereof in preparation of medicaments for treating or preventing radiation brain damage |
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| Title |
|---|
| 彭仕华 等: "6-甲氧基正丁苯酞的体内代谢转化研究", 《药学学报》 * |
| 彭仕华 等: "氯代正丁苯酞在大鼠肝微粒体中的代谢研究", 《药学学报》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112898224A (en) * | 2019-12-04 | 2021-06-04 | 中国科学院上海药物研究所 | Allyl alcohol-supported macrolide compound and application thereof |
| CN112898224B (en) * | 2019-12-04 | 2023-02-17 | 中国科学院上海药物研究所 | Allyl alcohol-supported macrolide compound and application thereof |
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