CN1850275A - Chiral drug intercalation hydrotalcite and its preparing method - Google Patents
Chiral drug intercalation hydrotalcite and its preparing method Download PDFInfo
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- CN1850275A CN1850275A CNA2006100113876A CN200610011387A CN1850275A CN 1850275 A CN1850275 A CN 1850275A CN A2006100113876 A CNA2006100113876 A CN A2006100113876A CN 200610011387 A CN200610011387 A CN 200610011387A CN 1850275 A CN1850275 A CN 1850275A
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- levodopa
- chiral drug
- anion
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Abstract
The present invention provides a chiral medicine intercalated hydrotalcite and its preparation method. The described chiral medicine is levodopa, said chiral medicine levodopa can be inlaid into the interlamination of hydrotalcite so as to obtain the invented product chiral medicine intercalated hydrotalcite with the effect of resisting Parkinson's disease. Said invention also provides its chemical structure formula.
Description
Technical field
The invention belongs to the antiparkinsonism drug technical field, a kind of chiral drug intercalation hydrotalcite and preparation method thereof particularly is provided.
Technical background
Parkinson disease, promptly usually said Parkinsonism is a kind of common delayed ischemic neurological deficits disease, mainly influences middle-aged and elderly people, and mostly at 60 years old with sequela.Its symptom shows as hands when static, head or mouth and does not independently tremble, and muscular rigidity, motion slowly and postural balance obstacle etc. cause can't take care of oneself.Find according to the study, the a group that is positioned at human brain midbrain position is the neuronic neurocyte of black substance, neurotransmitter by synthetic a kind of " dopamine " comes the motor function of brain is regulated and control, and when these black substance neuronal degeneration death reach 80% when above, symptoms of Parkinson's disease will occur.
Levodopa is the dopamine precursor, in vivo by aromatic l-amino acid decarboxylase effect biosynthesis dopamine; Since levodopa alkalescence a little less than, thereby can see through blood brain barrier, decarboxylation generation dopamine and bring into play pharmacological action in brain.Gone on the market and be widely used in the treatment parkinson disease as levodopa standard film, levodopa capsule of with the levodopa being main component etc., but these medicines must be to preserve covering under light and the sealing of strictness, and find that according to medical research the patient takes the levodopa standard film and the motor fluctuation symptom can occur, so used levodopa controlled release tablet (domestic have only Sinemet CR) instead.Though brucite has been widely used in field of medicaments (as gastric antiacids, anti-inflammatory agent, anti-osteoporotic etc.), still there are not at present both at home and abroad document and patent report that relevant hydrotalcite stratified material is applied to treat the chiral drug field of anti-parkinson.
Summary of the invention
The object of the present invention is to provide a kind of chiral drug intercalation hydrotalcite system and preparation method thereof, obtain a kind of drug effect in storage with take brucite antiparkinsonism drug relatively stable in the process, with solve this chiral drug of present levodopa on the storage condition restriction and take the slow release problem of back drug effect.
Chiral drug intercalation hydrotalcite antiparkinsonism drug of the present invention can keep the configuration of chiral drug to guarantee drug effect in its storage process by the space confinement effect of hydrotalcite layers; Take the effect that can play the drug effect slow release in the process by the host-guest interaction of brucite laminar composite at it, main body wherein also can play the effect of controlled release agent simultaneously.
The composition of chiral drug intercalation hydrotalcite antiparkinsonism drug of the present invention is: chemical formula is:
M
N+ 1-xM
3+ x(OH)
2(C
9H
11NO
4)
a(CO
3)
bMH
2O utilizes ion exchange to replace the NO of precursor hydrotalcite layers chiral drug levodopa anion
3 -Perhaps Cl
-, constitute the anionic supermolecule stratified material that chiral drug levodopa anion accounts for hydrotalcite layers anion molal quantity sum 20%～90%.Wherein: M
N+, M
3+Be monovalence metal cation Li
+With trivalent metal cation combination or selection divalent metal Mg
2+, Ca
2+In any and trivalent metal cation Al
3+, Fe
3+In any combination; N gets 1 or 2; The span of x is 0.2～0.33.
The preparation process of chiral drug intercalation hydrotalcite antiparkinsonism drug of the present invention is as follows:
A. be under 9.0～12.0 conditions at pH value, preparation laminate monovalence, Tricationic mol ratio M
+/ M
3+=0.5～3.0 or bivalence, Tricationic mol ratio M
2+/ M
3+=2.0～4.0, interlayer anion is NO
3 -Perhaps Cl
-The brucite precursor;
B. the chiral drug levodopa is joined and utilize in the weakly alkaline solution that NaOH or ammonia makes, secure ph is 4.0～9.0 system, thereby obtains the chiral drug levodopa ion with certain negative charge amount;
C. according to mol ratio chiral drug levodopa/brucite precursor=0.5～3.0, with the brucite precursor of step a preparation at shading, N
2Protection is also stirred down, joins in the system of step b preparation, and adjust pH is 6.0～9.0, carries out ion-exchange reactions 0.5～5 day first time under the room temperature, and product spends CO
2, the abundant centrifuge washing of deionized water separates 1～6 time;
D. the precipitation that centrifugalize among the step c is obtained joins in the system of step b preparation, and adjust pH is 6.0～9.0, carries out ion-exchange reactions 0.5～5 day second time under the room temperature, and product spends CO
2, the abundant centrifuge washing of deionized water separates 1～6 time; Can obtain chiral drug intercalation hydrotalcite behind the vacuum drying under the room temperature.
It is primary ions exchange or repeatedly ion exchange that the present invention prepares the ion exchange that chiral drug intercalation hydrotalcite adopts.
With above-mentioned prepared material:
1. carry out XRD, IR, NMR, elemental analysis demonstration chiral drug to the success of hydrotalcite layers intercalation.The composite interlamellar spacing of XRD data show after chirality is medicament intercalated increases, and its cell parameter a value remains unchanged in the intercalation front and back, has complete layer structure;
2. carrying out In-situ XRD, In-situ IR, TG-DTA, TG-MAS characterizes the heat stability that shows this composite and has had and significantly improve;
3. carry out UV-vis, polariscope, its optical stability maintenance of chiral column HPLC sign demonstration well;
4. carry out in-vitro simulated release experiment and show that this composite system can reach certain sustained release performance.
The invention has the advantages that: adopt repeatedly successive ion exchange fully to react by guarantee system; Utilize the space confinement effect of brucite stratified material and the interaction between the Subjective and Objective, the chiral drug levodopa with anti-parkinson drug effect is assembled into hydrotalcite layers, realize the effective storage of brucite chiral drug; Reach the sustained release performance of brucite simultaneously, a kind of " storage-administration " new way that brucite is applied to this chiral drug is provided this chiral drug.
Description of drawings
The XRD spectra of Fig. 1 for obtaining under the embodiment of the invention 3 assembling conditions; Abscissa is 2 θ, unit: degree; Vertical coordinate is an intensity.Wherein: a is levodopa intercalated houghite (Levodopa-LDHs); B is nitrate anion brucite (NO between precursor layer
3-MgAl-LDHs).
The IR spectrogram of Fig. 2 for obtaining under the embodiment of the invention 3 assembling conditions; Abscissa is a wave number, unit: cm-1; Vertical coordinate is a transmitance.Wherein: c is nitrate anion brucite (NO between precursor layer
3-MgAl-LDHs); D is levodopa intercalated houghite (Levodopa-LDHs); E is levodopa (Levodopa).
The UV-vis spectrogram of Fig. 3 for obtaining under the embodiment of the invention 3 assembling conditions; Abscissa is a wavelength, unit: nm; Vertical coordinate is an absorbance.Wherein: f is levodopa (Levodopa); G is levodopa intercalated houghite (Levodopa-LDHs).
The specific embodiment
[embodiment 1]
Steps A: take by weighing 15.36g Mg (NO
3)
2.6H
2O and 11.25g Al (NO
3)
3.9H
2O is dissolved in 150ml and removes CO
2, deionized water preparation mixing salt solution, other gets 7.2g NaOH and is dissolved in 200ml and removes CO
2, deionized water and being positioned in the 500mL four-hole boiling flask; Adopt single coprecipitation, at 70 ℃ of water-baths, N
2Under protection, the strong agitation condition the former saline solution slowly is added drop-wise in latter's aqueous slkali, regulates pH value to 10.0, reaction 40h; The product washing and filtering is to pH＜8.0; Keep a large amount of fresh filter cakes in order to ion exchange usefulness, only take out small amount of sample and characterize behind the dry 18h down, obtain NO at 70 ℃
3-Mg
2Al-LDHs, its Mg
2+/ Al
3+=2.
Step B:, take by weighing 0.6g (about 3mmol) Levodopa earlier and be dissolved in 400mL and remove CO according to mol ratio chiral drug levodopa/brucite precursor=3
2, deionized water and place the 500mL four-hole boiling flask; Take by weighing 3.6g (about lmmol) again and add wherein, cover light, N by the filter cake that steps A makes
2Protection, strong agitation, regulating pH is 7.8, ion exchange 2d under the room temperature; Product spends CO
2, deionized water wash centrifugalize 5 times, will precipitate drying at room temperature in a vacuum, can obtain interlayer and contain the anionic laminar composite of levodopa.
Step C: in-vitro simulated release, the standard curve of making levodopa takes by weighing the composite that is made by step B in right amount more earlier, is 7.4 KH with pH
2PO
3Buffer solution is release medium, is to discharge continuously in 37 ± 0.5 ℃ the constant temperature water bath agitator in temperature, and rotating speed is 100r/min, and the timing sampling analysis obtains release profiles.
It is Mg that elementary analysis can get chemical formula
4.64Al
2.25(OH)
13.78(C
9H
11NO
4)
1.05(CO
3)
0.604.12H
2O.By XRD figure as can be known, the levodopa anion is after ion exchange enters the LDHs interlayer, and its laminate spacing increases to 1.30nm by the 0.86nm of precursor; Two kinds of LDHs have the obvious diffraction peak near 2 θ are 61 °, and corresponding cell parameter a is approximately 0.30nm, illustrates that the anion intercalated front and back of levodopa LDHs laminate charge density does not change, and the LDHs laminate obtains more complete maintenance.The IR spectrogram shows, preparation-obtained Levodopa-Mg
2Al-LDHs is at 1591cm
-1, 1493cm
-1, 1363cm
-1, 1258cm
-1The characteristic peak of levodopa occurred at the place, UV-vis the analysis showed that the ultraviolet absorption peak of the levodopa that near 280nm appearance is strong simultaneously, proves the anion intercalated success of levodopa.By the heat analysis as can be known, the interlayer object of composite decomposes just beginning more than 280 ℃, illustrates that its heat stability increases significantly.By the optical activity test as can be known, this composite can keep the interlayer object more than 95% that raceme does not take place generally speaking, promptly has significantly effectively storage performance.Be 30%～60% by burst size in the simulation slow release test shows pro-40min in addition, and burst size is 50%～100% behind 100min, thereby has the good slow release effect is arranged.
[embodiment 2]
Steps A: take that the steps A method prepares NO in the similar embodiment 1
3-Mg
2The Al-LDHs precursor.
Step B:, take by weighing 0.8g (about 4mmol) Levodopa earlier and be dissolved in 400mL and remove CO according to mol ratio chiral drug levodopa/brucite precursor=2
2, deionized water and being positioned in the 500mL four-hole boiling flask; Take by weighing 7.0g (about 2mmol) again and add wherein, cover light, N by the filter cake that steps A makes
2Protection, strong agitation, regulating pH is 7.8, ion exchange 2d under the room temperature; Product spends CO
2, deionized water wash centrifugalize 5 times, will precipitate drying at room temperature in a vacuum, can obtain interlayer and contain the anionic laminar composite of levodopa.
Step C: take step C method in the similar embodiment 1, carry out in-vitro simulated release test, thereby obtain release profiles.
It is Mg that elementary analysis can get chemical formula
4.64Al
2.25(OH)
13.78(C
9H
11NO
4)
0.97(CO
3)
0.644.23H
2O.By XRD figure as can be known, the levodopa anion is after ion exchange enters the LDHs interlayer, and its laminate spacing increases to 1.31nm by the 0.86nm of precursor; Two kinds of LDHs have the obvious diffraction peak near 2 θ are 61 °, and corresponding cell parameter a is approximately 0.30nm, illustrates that the anion intercalated front and back of levodopa LDHs laminate charge density does not change, and the LDHs laminate obtains more complete maintenance.The IR spectrogram shows, preparation-obtained Levodopa-Mg
2Al-LDHs is at 1591cm
-1, 1493cm
-1, 1363cm
-1, 1258cm
-1The characteristic peak of levodopa occurred at the place, UV-vis the analysis showed that the ultraviolet absorption peak of the levodopa that near 280nm appearance is strong simultaneously, proves the anion intercalated success of levodopa.By the heat analysis as can be known, the interlayer object of composite decomposes just beginning more than 280 ℃, illustrates that its heat stability improves.By the optical activity test as can be known, this composite can keep the interlayer object more than 95% that raceme does not take place generally speaking, promptly has significantly effectively storage performance.Be 40%～60% by burst size in the simulation slow release test shows pro-40min in addition, and burst size is 60%～100% behind 100min, thereby has the good slow release effect is arranged.
[embodiment 3]
Steps A: take that the steps A method prepares NO in the similar embodiment 1
3-Mg
2The Al-LDHs precursor.
Step B: according to step B method in the similar embodiment 2, carry out the ion-exchange reactions 2d first time after, product spends CO
2, deionized water wash, centrifugalize 5 times, obtain precipitated product.
Step C: take by weighing 0.5g (about 2.5mmol) Levodopa and be dissolved in 400mL and remove CO
2, deionized water and being positioned in the 500mL four-hole boiling flask; Covering light, N
2Protection, under the strong agitation condition, in the precipitation adding system that will be made by above step B, regulating pH is 7.8, carries out ion exchange second time 2d under the room temperature; Product spends CO
2, deionized water wash centrifugalize 5 times, will precipitate drying at room temperature in a vacuum, can obtain interlayer and contain the anionic laminar composite of levodopa.
Step D: take step C method in the similar embodiment 1, carry out in-vitro simulated release test, thereby obtain release profiles.
It is Mg that elementary analysis can get chemical formula
4.64Al
2.25(OH)
13.78(C
9H
11NO
4)
1.35(CO
3)
0.453.89H
2O.By XRD figure as can be known, the levodopa anion is after ion exchange enters the LDHs interlayer, and its laminate spacing increases to 1.31nm by the 0.86nm of precursor; Two kinds of LDHs have the obvious diffraction peak near 2 θ are 61 °, and corresponding cell parameter a is approximately 0.30nm, illustrates that the anion intercalated front and back of levodopa LDHs laminate charge density does not change, and the LDHs laminate obtains more complete maintenance.The IR spectrogram shows, preparation-obtained Levodopa-Mg
2Al-LDHs is at 1591cm
-1, 1493cm
-1, 1363cm
-1, 1258cm
-1The characteristic peak of levodopa occurred at the place, UV-vis the analysis showed that the ultraviolet absorption peak of the levodopa that near 280nm appearance is strong simultaneously, proves the anion intercalated success of levodopa.By the heat analysis as can be known, the interlayer object of composite decomposes just beginning more than 280 ℃, illustrates that its heat stability improves.By the optical activity test as can be known, this composite can keep the interlayer object more than 95% that raceme does not take place generally speaking, promptly has significantly effectively storage performance.Be 40%～60% by burst size in the simulation slow release test shows pro-40min in addition, and burst size is 60%～100% behind 100min, thereby has the good slow release effect is arranged.
[embodiment 4]
Steps A: take that the steps A method prepares NO in the similar embodiment 1
3-Mg
2The Al-LDHs precursor.
Step B: according to step B method in the similar embodiment 2, carry out the ion-exchange reactions 24h first time after, product spends CO
2, deionized water wash, centrifugalize 5 times, obtain precipitated product.
Step C: take step C method in the similar embodiment 3, carry out ion exchange second time 3d under the room temperature; Product spends CO
2, deionized water wash centrifugalize 5 times, will precipitate drying at room temperature in a vacuum, can obtain interlayer and contain the anionic laminar composite of levodopa.
Step D: take step C method in the similar embodiment 1, carry out in-vitro simulated release test, thereby obtain release profiles.
It is Mg that elementary analysis can get chemical formula
4.64Al
2.25(OH)
13.78(C
9H
11NO
4)
0.85(CO
3)
0.703.91H
2O.By XRD figure as can be known, the levodopa anion is after ion exchange enters the LDHs interlayer, and its laminate spacing increases to 1.46nm by the 0.86nm of precursor; Two kinds of LDHs have the obvious diffraction peak near 2 θ are 61 °, and corresponding cell parameter a is approximately 0.31nm, illustrates that the anion intercalated front and back of levodopa LDHs laminate charge density does not change, and the LDHs laminate obtains more complete maintenance.The IR spectrogram shows, preparation-obtained Levodopa-Mg
2Al-LDHs is at 1591cm
-1, 1493cm
-1, 1363cm
-1, 1258cm
-1The characteristic peak of levodopa occurred at the place, UV-vis the analysis showed that the ultraviolet absorption peak of the levodopa that near 280nm appearance is strong simultaneously, proves the anion intercalated success of levodopa.By the heat analysis as can be known, the interlayer object of composite decomposes just beginning more than 280 ℃, illustrates that its heat stability improves.By the optical activity test as can be known, this composite can keep the interlayer object more than 95% that raceme does not take place generally speaking, promptly has significantly effectively storage performance.Be 40%～70% by burst size in the simulation slow release test shows pro-40min in addition, and burst size is 50%～100% behind 100min, thereby has the good slow release effect is arranged.
[embodiment 5]
Steps A: take by weighing 2.54g LiCl and 4.83g AlCl
3.6H
2O is dissolved in 100ml and removes CO
2, deionized water preparation mixing salt solution, other gets 4.0g NaOH and is dissolved in 250ml and removes CO
2, deionized water and being positioned in the 500mL four-hole boiling flask; Adopt single coprecipitation, at 65 ℃ of water-baths, N
2Under protection, the strong agitation condition the former saline solution slowly is added drop-wise in latter's aqueous slkali, regulating pH value is 10.5, reaction 6h; The product washing and filtering is to pH＜8.0; Keep a large amount of fresh filter cakes in order to ion exchange usefulness, only take out small amount of sample and characterize behind the dry 18h down, obtain Cl-Li at 70 ℃
3Al-LDHs, its Li
+/ Al
3+=3.
Step B:, take by weighing 0.6gLevodopa earlier and be dissolved in 400mL and remove CO according to mol ratio chiral drug levodopa/brucite precursor=2
2, deionized water and being positioned in the 500mL four-hole boiling flask; Take by weighing the filter cake that makes by steps A in right amount again and add wherein, cover light, N
2Protection, strong agitation, regulating pH is 7.9, ion exchange 2d under the room temperature; Product spends CO
2, deionized water wash centrifugalize 5 times, will precipitate drying at room temperature in a vacuum, can obtain interlayer and contain the anionic laminar composite of levodopa.
It is Li that elementary analysis can get chemical formula
3.43Al
1.13(OH)
4.56(C
9H
11NO
4)
0.62(CO
3)
0.824.31H
2O.By XRD figure as can be known, the levodopa anion is after ion exchange enters the LDHs interlayer, and its laminate spacing increases to 1.20nm by the 0.77nm of precursor; Two kinds of LDHs have the obvious diffraction peak near 2 θ are 61 °, and corresponding cell parameter a is approximately 0.30nm, illustrates that the anion intercalated front and back of levodopa LDHs laminate charge density does not change, and the LDHs laminate obtains more complete maintenance.The IR spectrogram shows that preparation-obtained sample is at 1591cm
-1, 1493cm
-1, 1363cm
-1, 1258cm
-1The characteristic peak of levodopa occurred at the place, UV-vis the analysis showed that the ultraviolet absorption peak of the levodopa that near 280nm appearance is strong simultaneously, proves the anion intercalated success of levodopa.
Claims (2)
1, a kind of chiral drug intercalation hydrotalcite is characterized in that: chemical formula is: Mn
+ 1-xM
3+x(OH)
2(C
9H
11NO
4)
a(CO
3)
bMH
2O utilizes ion exchange to replace the NO of precursor hydrotalcite layers chiral drug levodopa anion
3 -Perhaps Cl
-, constitute the anionic supermolecule stratified material that chiral drug levodopa anion accounts for hydrotalcite layers anion molal quantity sum 20%～90%; Wherein: M
N+, M
3+Be monovalence metal cation Li
+With trivalent metal cation combination or selection divalent metal Mg
2+, Ca
2+In any and trivalent metal cation Al
3+, Fe
3+In any combination; N gets 1 or 2; The span of x is 0.2～0.33.
2, a kind of method for preparing the described chiral drug intercalation hydrotalcite of claim 1 is characterized in that:
A. be under 9.0～12.0 conditions at pH value, preparation laminate monovalence, Tricationic mol ratio M
+/ M
3+=0.5～3.0 or bivalence, Tricationic mol ratio M
2+/ M
3+=2.0～4.0, interlayer anion is NO
3 -Perhaps Cl
-The brucite precursor; Described brucite main body laminate is selected monovalence metal cation Li
+With trivalent metal cation combination or selection divalent metal Mg
2+, Ca
2+In any and trivalent metal cation Al
3+, Fe
3+In any combination;
B. the chiral drug levodopa is joined and utilize in the weakly alkaline solution that NaOH or ammonia makes, secure ph is 4.0～9.0 system, thereby obtains the chiral drug levodopa ion with certain negative charge amount;
C. according to mol ratio chiral drug levodopa/brucite precursor=0.5～3.0, with the brucite precursor of step a preparation at shading, N
2Protection is also stirred down, joins in the system of step b preparation, and adjust pH is 6.0～9.0, carries out ion-exchange reactions 0.5～5 day first time under the room temperature, and product spends CO
2, the abundant centrifuge washing of deionized water separates 1～6 time;
D. the precipitation that centrifugalize among the step c is obtained joins in the system of step b preparation, and adjust pH is 6.0～9.0, carries out ion-exchange reactions 0.5～5 day second time under the room temperature, and product spends CO
2, the abundant centrifuge washing of deionized water separates 1～6 time; Can obtain chiral drug intercalation hydrotalcite behind the vacuum drying under the room temperature.
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|---|---|---|---|
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ID=37131786
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010025632A1 (en) * | 2008-09-05 | 2010-03-11 | 北京化工大学 | A methods for preparing the clathrate compound of steroid medicines utilizing hydrotalcite as carrier |
| CN100998872B (en) * | 2007-01-16 | 2010-12-08 | 北京化工大学 | Polypeptide medicine intercalation hydrotalcite and its preparation method |
| CN101773487B (en) * | 2010-01-15 | 2011-12-07 | 北京化工大学 | Exotic plant Flaveria bidentis active ingredient chlorogenic acid intercalation hydrotalcite and preparation method thereof |
-
2006
- 2006-02-28 CN CNA2006100113876A patent/CN1850275A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN100998872B (en) * | 2007-01-16 | 2010-12-08 | 北京化工大学 | Polypeptide medicine intercalation hydrotalcite and its preparation method |
| WO2010025632A1 (en) * | 2008-09-05 | 2010-03-11 | 北京化工大学 | A methods for preparing the clathrate compound of steroid medicines utilizing hydrotalcite as carrier |
| CN101773487B (en) * | 2010-01-15 | 2011-12-07 | 北京化工大学 | Exotic plant Flaveria bidentis active ingredient chlorogenic acid intercalation hydrotalcite and preparation method thereof |
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