CN102977022B - (-)-meptazinol phenyl urethan-L-(+)-tartrate IV type crystal - Google Patents
(-)-meptazinol phenyl urethan-L-(+)-tartrate IV type crystal Download PDFInfo
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- CN102977022B CN102977022B CN201210473827.5A CN201210473827A CN102977022B CN 102977022 B CN102977022 B CN 102977022B CN 201210473827 A CN201210473827 A CN 201210473827A CN 102977022 B CN102977022 B CN 102977022B
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Abstract
The present invention relates to () meptazinol phenyl urethan L (+) tartrate IV type crystal and preparation method.nullThe invention provides a kind of stable () meptazinol phenyl urethan L (+) tartrate IV type crystal，It is characterized in that the position at the characteristic peak 2 θ angle that X-ray powder diffraction figure shows respectively: 9.7、10.7、12.6、15.1、15.9、16.9、17.3、18.6、19.0、19.9、20.6、21.3、22.1、23.0、24.2、25.4、27.4、28.3、28.8、31.1、31.9、33.5、35.8°2θ，The relative intensity at corresponding peak is respectively as follows: 16、47、21、16、100、10、12、11、13、35、25、72、22、83、22、11、10、10、10、11、11、10、10.Its fusing point of crystal of the present invention is 90.9～93.2 DEG C.
Description
Present disclosure relates to (-)-meptazinol phenyl urethan-L-(+)-tartrate IV type crystal and system
Preparation Method.
Background technology Chinese patent application 200710038209.7 disclose a kind of have treatment dementia effect (-)-Mei Pu
His phenol carbanilic acid ester compounds and salt thereof.Animal experiment discovery (-)-meptazinol phenyl urethan-L-(+)-winestone
Hydrochlorate activity is preferable, is possible drug candidate, but test find unbodied (-)-meptazinol phenyl urethan-L-
(+)-tartrate stability is undesirable, is not suitable for doing pharmaceutical preparation.Prior art exigence a kind of stable (-)-beautiful
His phenol phenyl urethan-L-general (+)-tartrate is used for preparing pharmaceutical preparation.
Summary of the invention
The goal of the invention of the present invention is: provide a kind of stable (-)-meptazinol phenyl urethan-L-(+)-winestone
Hydrochlorate.
Through substantial amounts of experimental study, the inventors discovered that a kind of stable (-)-meptazinol phenyl urethan-
L-(+)-tartrate IV type crystal.
The technical scheme is that one (-)-meptazinol phenyl urethan-L-(+)-tartrate IV type is brilliant
Body, is characterized in that the position at the characteristic peak 2 θ angle that X-ray powder diffraction figure shows respectively: 9.7,10.7,12.6,15.1,
15.9、16.9、17.3、18.6、19.0、19.9、20.6、21.3、22.1、23.0、24.2、25.4、27.4、28.3、28.8、
31.1,31.9,33.5,35.8 ° of 2 θ, the relative intensity at corresponding peak is respectively as follows: 16,47,21,16,100,10,12,11,13,
35、25、72、22、83、22、11、10、10、10、11、11、10、10。
The present invention (-)-meptazinol phenyl urethan-L-(+)-tartrate IV type crystal, its infrared spectrum shows
Characteristic absorption cm-1Be expressed as: 3317.6,2966.5,1716.7,1600.9,1541.1,1444.7,1205.5,
1124.5、1066.6、1016.5、995.3、904.6、804.3、760.0、696.3、507.3、484.1。
The present invention (-)-meptazinol phenyl urethan-L-(+)-tartrate IV type crystal, its fusing point is: 90.9～
93.2℃。
The present invention (-)-meptazinol phenyl urethan-L-(+)-tartrate IV type crystal, it is characterized in that differential is swept
Retouching the absworption peak of calorimetry differential thermogram at about 86～95 DEG C, peak value is at about 92 DEG C.
The present invention (-)-meptazinol phenyl urethan-L-(+)-tartrate IV type crystal, its preparation method is: take
(-)-meptazinol phenyl urethan-L-(+)-tartrate amorphous substance puts in single port flask, add oxolane and dissolve,
Stand crystallize 5 days at 30 DEG C, be filtrated to get white crystal.
The present invention (-)-meptazinol phenyl urethan-L-(+)-preferred skill of tartrate IV type crystal preparation method
Art scheme, concentration is 5%～25% (mass volume ratio).
The present invention (-)-meptazinol phenyl urethan-L-(+)-preferred skill of tartrate IV type crystal preparation method
Art scheme, concentration is 20% (mass volume ratio).
The invention has the beneficial effects as follows: obtained a kind of stable present invention (-)-meptazinol phenyl urethan-L-
(+)-tartrate IV type crystal.
Accompanying drawing illustrates:
Fig. 1: (-)-meptazinol phenyl urethan-L-(+)-tartrate IV type crystal X-ray powder diffraction pattern.
Fig. 2: (-)-meptazinol phenyl urethan-L-(+)-tartrate IV type crystal infared spectrum.
Fig. 3: (-)-meptazinol phenyl urethan-L-(+)-tartrate IV type crystal differential scanning calorimetry differential
Thermal analysis curue.
Embodiment 1, in the single port bottle of 100ml, adds 12.5 grams of (-)-meptazinol phenyl urethan-L-(+)-wine
Stone hydrochlorate amorphous substance, 50ml oxolane dissolves, and stands crystallize 5 days, filter the crystal separated out, 60 DEG C of bakings in baking oven at 30 DEG C
Within 3 hours, obtain IV type crystal.9.7,10.7 it is characterized in that the position at the characteristic peak 2 θ angle that X-ray powder diffraction figure shows respectively:,
12.6、15.1、15.9、16.9、17.3、18.6、19.0、19.9、20.6、21.3、22.1、23.0、24.2、25.4、27.4、
28.3,28.8,31.1,31.9,33.5,35.8 ° of 2 θ, the relative intensity at corresponding peak is respectively as follows: 16,47,21,16,100,10,
12、11、13、35、25、72、22、83、22、11、10、10、10、11、11、10、10；The characteristic absorption that its infrared spectrum shows is used
cm-1Be expressed as: 3317.6,2966.5,1716.7,1600.9,1541.1,1444.7,1205.5,1124.5,1066.6,
1016.5、995.3、904.6、804.3、760.0、696.3、507.3、484.1；Its fusing point is: 90.9～93.2 DEG C of its differentials
The absworption peak of scanning calorimetry differential thermogram is at about 86～95 DEG C, and peak value is at about 92 DEG C.
Embodiment 2, in the single port bottle of 100ml, adds 3 grams of (-)-meptazinol phenyl urethan-L-(+)-tartaric acid
Salt amorphous substance, 60ml oxolane dissolves, and stands crystallize 5 days, filter the crystal separated out at 30 DEG C, and in baking oven, 50 DEG C of bakings 3 are little
Time obtain IV type crystal, it is characterized in that the position at the characteristic peak 2 θ angle that X-ray powder diffraction figure shows respectively: 9.7,10.7,
12.6、15.1、15.9、16.9、17.3、18.6、19.0、19.9、20.6、21.3、22.1、23.0、24.2、25.4、27.4、
28.3,28.8,31.1,31.9,33.5,35.8 ° of 2 θ, the relative intensity at corresponding peak is respectively as follows: 16,47,21,16,100,10,
12、11、13、35、25、72、22、83、22、11、10、10、10、11、11、10、10；The characteristic absorption that its infrared spectrum shows is used
cm-1Be expressed as: 3317.6,2966.5,1716.7,1600.9,1541.1,1444.7,1205.5,1124.5,1066.6,
1016.5、995.3、904.6、804.3、760.0、696.3、507.3、484.1；Its fusing point is: 90.9～93.2 DEG C；Its differential
The absworption peak of scanning calorimetry differential thermogram is at about 86～95 DEG C, and peak value is at about 92 DEG C.
Test example 1:
According to Chinese patent application 200710038209.7 provide cholinesterase inhibition method of testing measure (-)-
Meptazinol phenyl urethan-L-(+)-tartrate IV type crystal is to AChE's in rat brain homogenate and rat blood serum BChE
Inhibitory activity record is in Table 1.
Table 1
Experimental data shows, (-)-meptazinol phenyl urethan-L-(+)-tartrate IV type crystal is to rat brain
In homogenate, AChE and rat blood serum BChE has certain inhibitory activity.
Test example 2: study on the stability
The embodiment 1 being placed in open-top receptacle～embodiment 2 sample and (-)-meptazinol phenyl urethan-L-
The amorphous powder of (+)-tartrate, is placed in climatic chamber, is 40 DEG C in temperature, under the conditions of relative humidity 65%, examines
Examine stability.Respectively at 0 day, 5 days, 10 days sampling detection level, detection data were reported in Table 2 below.
Table 2
Experimental data shows: left-handed meptazinol phenyl urethan-L-(+) stability of-tartrate IV type crystal
Than left-handed meptazinol phenyl urethan-L-(+) stability of the amorphous powder of-tartrate is much better, to preparation
Preparation have positive meaning.
Claims (4)
1. one kind (-)-meptazinol phenyl urethan-L-(+)-tartrate IV type crystal, it is characterised in that X-ray powder
The end characteristic peak positions that shows of diffraction pattern is: 9.7,10.7,12.6,15.1,15.9,16.9,17.3,18.6,
19.0、 19.9、20.6、 21.3、 22.1、 23.0、 24.2、 25.4、 27.4、 28.3、 28.8、 31.1、 31.9、
33.5,35.8 ° of 2 θ, the relative intensity at corresponding peak is respectively as follows: 16,47,21,16,100,10,12,11,13,
35、 25、 72、 22、 83、 22、 11、 10、 10、 10、11、 11、 10、 10。
The most according to claim 1 (-)-meptazinol phenyl urethan-L-(+)-tartrate IV type crystal, its feature exists
In, fusing point is: 90.9-93.2 DEG C.
The most according to claim 1 (-)-meptazinol phenyl urethan-L-(+)-tartrate IV type crystal, its feature exists
In, the absworption peak of differential scanning calorimetry differential thermogram is at 86-95 DEG C, and peak value is at 92 DEG C.
The most according to claim 1 (-)～meptazinol phenyl urethan-L-(+) the preparation side of-tartrate IV type crystal
Method, it is characterised in that unbodied (-)-meptazinol phenyl urethan-L-(+)-tartrate is dissolved in oxolane,
Stand crystallize at 30 DEG C, filter.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1850804A (en) * | 2006-03-31 | 2006-10-25 | 复旦大学 | Optical-purity meptazinol orits salts, and preparing method |
| CN101020661A (en) * | 2007-03-19 | 2007-08-22 | 复旦大学 | (-)-meptazinol carbamate derivative and/or its salt and their prepn and use |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1850804A (en) * | 2006-03-31 | 2006-10-25 | 复旦大学 | Optical-purity meptazinol orits salts, and preparing method |
| CN101020661A (en) * | 2007-03-19 | 2007-08-22 | 复旦大学 | (-)-meptazinol carbamate derivative and/or its salt and their prepn and use |
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Effective date of registration: 20160822 Address after: 264205 No. 1 South Qingdao Road, Weihai economic and technological development, Shandong Applicant after: Disha Pharmaceutical Industry Group Corp., Ltd. Applicant after: Weihai Disu Pharmaceutical Co., Ltd. Address before: 264205 No. 1 South Qingdao Road, Weihai economic and technological development, Shandong Applicant before: Disha Pharmaceutical Industry Group Corp., Ltd. Applicant before: Disha Pharmaceutical Group Shandong Disha Pharmaceutical Co., Ltd. Applicant before: Weihai Disu Pharmaceutical Co., Ltd. Applicant before: Weihai Weitai Medical Technology Development Co., Ltd. |
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