CN102702033A - Amorphous peramivir, preparation method thereof and medicinal composition - Google Patents
Amorphous peramivir, preparation method thereof and medicinal composition Download PDFInfo
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- CN102702033A CN102702033A CN2012101886523A CN201210188652A CN102702033A CN 102702033 A CN102702033 A CN 102702033A CN 2012101886523 A CN2012101886523 A CN 2012101886523A CN 201210188652 A CN201210188652 A CN 201210188652A CN 102702033 A CN102702033 A CN 102702033A
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Abstract
The invention discloses an amorphous peramivir crystal form. The chemical purity and the crystal form purity of the amorphous peramivir are both more than 95 percent, and the amorphous peramivir does not contain crystal water or other crystal solvents; and meanwhile, the invention also discloses a preparation method for the amorphous peramivir, and further discloses a medicinal composition containing the amorphous peramivir, and application of the composition to preparation of medicines for treating influenza virus and influenza virus.
Description
Technical field
The invention belongs to technical field of medicine, relate to the new crystal of having found a kind of neuraminidase influenza suppressor factor-unformed RWJ 270201 (peramivir); More specifically say so a kind of unformed RWJ 270201 and preparation method thereof and pharmaceutical composition.
Background technology
RWJ 270201, English peramivir by name, chemical being called (1S, 2S, 3R, 4R)-3-[(1S)-1-(kharophen)-2-ethyl-butyl]-4-guanidine radicals-2-hydroxyl-pentamethylene yl carboxylic acid.This medicine is to be the novel cyclopentanes resisiting influenza virus preparation of action target spot by BioCryst company exploitation with influenza virus surface glycoprotein neuraminidase; Through suppressing neuraminidase influenza (NA) interphase interaction; Stop the virion of filial generation to reach the effect that prevents and treats A type, Type B influenza in the release and the propagation of host cell; Have better tolerance, advantage such as side effect is little is a kind of anti-avian influenza virus medicine that has a extensive future.
Through the document retrieval, be published in Z.Naturforsch.2007 62b and roll up the 983-987 page or leaf about " Crystal Structure of the Trihydrate of the Neuraminidase Inhibitor C
15H
28N
4O
4(Peramivir), aPotential Influenza A/B and Avian-influenza (H5N1) Drug " article, reported the crystalline structure of RWJ 270201 trihydrate to belong to tetragonal system that spacer is P4
22
12,
Molecule number Z=32 in the structure cell; Simultaneously, the document has also been reported the crystalline structure of RWJ 270201 duohydrate, belongs to rhombic system, and spacer is C222,
Molecule number Z=32 in the structure cell.
Patent relevant with the crystal formation preparation method of RWJ 270201 in the existing technology comprises: publication number is the preparation method and the powder x-ray diffraction characteristic spectrum of the patented claim of CN1367776A two kinds of hydrates disclosing RWJ 270201, respectively called after crystal type A, crystal B-type; Publication number is that the patented claim of CN101367750A discloses RWJ 270201 semihydrate, monohydrate, sesqui hydrate, duohydrate, trihydrate and hexahydrated preparation method.Publication number is that the patented claim of CN101314579A discloses RWJ 270201 anhydrous crystal forms and preparation method thereof.At present, the bibliographical information of the relevant unformed RWJ 270201 of Shang Weijian.
The inventor has found unformed RWJ 270201 unexpectedly in experiment, it is different from the RWJ 270201 hydrate of known crystal type A, crystal B-type, anhydrous crystal forms and other various ratios, thereby has accomplished the present invention.
Summary of the invention
The state that one object of the present invention has been to provide unformed RWJ 270201 crystal-form substances to exist.
Another object of the present invention has been to provide the preparation method of unformed RWJ 270201 crystal formation solid matter.
Also purpose of the present invention has been to provide the pharmaceutical composition that contains unformed RWJ 270201 crystal formation.
For realizing above-mentioned purpose, the invention discloses following technology contents:
A kind of unformed RWJ 270201 new crystal is characterized in that, its chemical purity and crystal formation purity are all greater than 95% and do not contain crystal water or other recrystallisation solvents, and its structure is as shown in Figure 1; When using powder x-ray diffraction analysis to adopt CuK
αDiffraction peak position 2-Theta value during the radiation experiments condition (°), spacing d value
Diffraction peak relative intensity peak height value I/I
0(%) have following characteristic:
Its infrared absorption spectrum 3349,2964,2936,2877,2170,1654,1555,1460,1392,1334,1300,1261,1181,1147,1085,1036,993,963,783,757,695,594cm
-1The place has absorption peak to exist, wherein 2170,1036,695,594cm
-1For it presents the absorption peak position of unformed crystal formation characteristic.
The present invention further discloses the preparation method of unformed RWJ 270201, mainly is to adopt physical method that the anhydrous crystal forms RWJ 270201 is converted into unformed RWJ 270201.Comprise:
(1) destroys lattice;
(2) molecular transposition changes brilliant;
(3) through selecting the appropriate solvent dissolving raw material for use, then rapidly with removal of solvents;
Wherein (1) described employing physical method destruction lattice refers to: the anhydrous crystal forms RWJ 270201 is put into shredder, and the setting rotating speed is 300-500r/min, suspends 1-5min behind every 10-20min, behind the grinding 4-10h, prepares unformed RWJ 270201;
Described (2) molecular transposition changes crystalline substance and refers to: the anhydrous crystal forms RWJ 270201 is adopted thermostatic heating method, under 120-250 ℃ of condition, keep 2-12h, reduce to room temperature then rapidly, prepare unformed RWJ 270201;
Described (3) are through selecting the appropriate solvent dissolving raw material for use; The rapid then method with removal of solvents refers to: the anhydrous crystal forms RWJ 270201 is mixed with single or mixed solvent; The dissolving back adopts spray method to remove solvent rapidly fully, prepares unformed RWJ 270201;
Described solvent is water, methyl alcohol, ethanol, acetone, n-propyl alcohol, Virahol, propyl carbinol, ETHYLE ACETATE, acetonitrile, THF, benzene, toluene, methylene dichloride, chloroform, normal hexane, hexanaphthene, dioxane, DMF, DMSO, ether, sherwood oil or pyridine.Preferred single solvent is water, methyl alcohol, ethanol or Virahol;
Preferred binary mixed solvent is a water: methyl alcohol, water: ethanol or water: Virahol; Water wherein: methyl alcohol, water: ethanol or water: the volume ratio of Virahol is 1: 0.1～1.
Multiple mixed solvent refers to: water: methyl alcohol: acetone; Water: methyl alcohol: the volume ratio of acetone is 1: 0.1～1: 0.1～0.5.
The present invention further discloses and contain unformed RWJ 270201 new crystal and pharmaceutically acceptable one or more pharmaceutical excipients of treating significant quantity.Be mainly tablet, capsule, injection liquid or freeze-dried powder.Wherein tablet or capsule contain the unformed RWJ 270201 of 5-1000mg; Injection liquid or freeze-dried powder contain the unformed RWJ 270201 of 100-400mg.
The unformed RWJ 270201 new crystal of the present invention's preparation has following characteristic:
1. the morphological specificity of unformed RWJ 270201:
1.1 the unformed RWJ 270201 that the present invention relates to, its chemical purity and crystal formation purity are all greater than 95% and do not contain crystal water or other recrystallisation solvents, when using powder x-ray diffraction analysis to adopt CuK
αDiffraction peak position 2-Theta value during the radiation experiments condition (°), spacing d value
Diffraction peak relative intensity peak height value I/I
0(%) have as shown in table 1 below:
Instrument: Japanese D/max-2500 powder x-ray diffraction of science; Experiment condition: the Cu-Ka radiation, pipe is pressed 40KV, pipe stream 100mA, 0.04 ° at step angle, 0.5 second computing time, sweep velocity: 8 °/min, graphite monochromator, sweep limit 3-80 °.
Table 1 provides the powder x-ray diffraction peak value meter of unformed RWJ 270201, and accompanying drawing 1 provides the x-ray diffractogram of powder spectrum of unformed RWJ 270201.
The powder x-ray diffraction peak value of the unformed RWJ 270201 of table 1
1.2 the unformed RWJ 270201 that the present invention relates to; Its morphological specificity is when the KBr compressing tablet that uses ir spectra is analyzed, 3349,2964,2936,2877,2170,1654,1555,1460,1392,1334,1300,1261,1181,1147,1085,1036,993,963,783,757,695,594cm
-1The place has absorption peak to exist, wherein 2170,1036,695,594cm
-1For it presents the absorption peak position of unformed crystal formation characteristic.
Instrument: the Magna-560 of Nicolet company type IR, KBr compressing tablet.Accompanying drawing 2 provides the infrared absorpting light spectra of unformed RWJ 270201.
2. the preparation method characteristic of unformed RWJ 270201:
2.1 use the anhydrous crystal forms RWJ 270201 to be the preparation raw material, obtain unformed RWJ 270201 through grinding.Mainly be that the anhydrous crystal forms RWJ 270201 is put into shredder, the setting rotating speed is 300-500r/min, suspends 1-5min behind every 10-20min, behind the grinding 4-10h, prepares unformed RWJ 270201.
2.2 use the anhydrous crystal forms RWJ 270201 for the preparation raw material, adopt thermostatic heating method, under 120-250 ℃ of condition, keep 2-12h, reduce to room temperature then rapidly, prepare unformed RWJ 270201.
2.3 make single solvent in water, methyl alcohol, ethanol, acetone, n-propyl alcohol, Virahol, propyl carbinol, ETHYLE ACETATE, acetonitrile, THF, benzene, toluene, methylene dichloride, chloroform, normal hexane, hexanaphthene, dioxane, DMF, DMSO, ether, sherwood oil or the pyridine different sorts solvent, arbitrarily two or more after different proportionings are mixed; The anhydrous crystal forms RWJ 270201 is dissolved fully; Adopt spray method to remove solvent rapidly, prepare unformed RWJ 270201.Preferred single solvent such as water, methyl alcohol, ethanol, Virahol.Preferred any two kinds of solvents such as water: methyl alcohol, water: ethanol or water: the volume ratio of Virahol is 1: 0.1～1.Preferred multiple warp different proportioning blended solvent such as water: methyl alcohol: the volume ratio of acetone is 1: 0.1～1: 0.1～0.5.
3. the stability features of unformed RWJ 270201:
The present invention has further investigated the stability of unformed RWJ 270201 by following condition, and its test-results is seen table 2.
3.1 exposure experiments to light: these article are laid in the flat weighing bottle, uncap, place under 4500lx ± 500lx illumination,, investigate the variation of outward appearance, related substance, content, crystal formation respectively at 5d, 10d sampling.
3.2 high temperature test: these article are laid in the flat weighing bottle, uncap, place 40 ℃ of thermostat containers,, investigate the variation of outward appearance, related substance, content, crystal formation respectively at 5d, 10d sampling.
3.3 high wet test: these article are laid in the flat weighing bottle, uncap, place in RH75% ± 5% moisture eliminator of (containing the saturated NaCl aqueous solution),, investigate the variation of outward appearance, related substance, content, crystal formation respectively at 5d, 10d sampling.
The stability test result of the unformed RWJ 270201 of table 2
Test-results: show that through illumination, high temperature, high humidity test the outward appearance of sample, related substance, content and crystal formation and 0d sample basically identical explain that these article are stable under illumination, high temperature, super-humid conditions.
4. the solvability characteristic of unformed RWJ 270201:
Test according to carrying out the solubility test of these article about the regulation of solubleness in " note of new drug (Western medicine) study of pharmacy governing principle ", and judge, obtain following result by solubleness note in 2010 editions notes on the use of Chinese Pharmacopoeia:
Unformed RWJ 270201 dissolves (the 1g sample can dissolve) in the water part omitted in 50-55mL water, and RWJ 270201 trihydrate slightly soluble (the 1g sample can dissolve in 160-170mL water) in water.
5. the crystal formation composition of unformed RWJ 270201, dosage and pharmaceutical preparations composition characteristic:
5.1 the present invention also provides a kind of pharmaceutical composition, said composition contains acceptable vehicle on unformed RWJ 270201 and the pharmacology of significant quantity on the pharmacology.General compsn oral administration, but also can other forms such as rectum, nose, part (comprising eyes, oral cavity and hypogloeeis), vagina and parenteral (comprising in subcutaneous, muscle, intravenously, intracutaneous, the sheath and exterior dura) administration.Though the form administration that unformed RWJ 270201 can pure compound is good with the form of pharmaceutical formulations.Being fit to oral form can be: tablet or capsule; Pulvis or granule; Solution in aqueous solution or non-aqueous liquid or suspension; Oil-in-water or water-in-oil-type liquid emulsion.
5.2 vehicle of the present invention comprises: thinner, weighting agent (like N.F,USP MANNITOL, lactose, polyoxyethylene glycol), tackiness agent (starch, Microcrystalline Cellulose), disintegrating agent (like CMC 99.5, low substituted hydroxypropylcellulose), lubricant (like talcum powder, Magnesium Stearate), wetting agent (like Ucar 35, ethanol), stablizer (EDTA-2Na, Sulfothiorine, Sodium Pyrosulfite, S-WAT, thanomin, sodium hydrogencarbonate, vitamin PP) or the like.Acceptable oral solid formulation has: conventional tablet, dispersible tablet, slow controlled release, enteric coated tablet, particle, capsule, dripping pill, powder or the like; Oral liquid has oral liquid, emulsion; Injection has: little liquid drugs injection, transfusion, freeze-dried powder or the like.General preparation can contain 5-1000mg, and preferred 10-800mg is more preferably the unformed RWJ 270201 of 100-800mg.Preferred composition is the injection liquid that contains the unformed RWJ 270201 of 100-400mg.Also can be tablet or the capsule that contains the unformed RWJ 270201 of 400-800mg.Optimum formulation is the injection liquid that contains the unformed RWJ 270201 of 100-400mg.Above-mentioned auxiliary material can be a common dose, mixes with unformed RWJ 270201 with proportioning commonly used, and after unformed RWJ 270201 consumption was confirmed, the proportioning between each pharmaceutical excipient can suitably be regulated as required.
The prepared unformed RWJ 270201 new crystal of the present invention is compared the positively effect that is had with existing crystal formation and is:
At first, compare with the RWJ 270201 hydrate preparation method of crystal type A, crystal B-type, anhydrous crystal forms and other various ratios of bibliographical information, the preparation method of unformed RWJ 270201 disclosed by the invention is simple, single, the no mixed crystal of gained crystal formation; Moreover, poorly soluble and lose crystal water easily because the RWJ 270201 hydrate of crystal type A, crystal B-type and other various ratios is moisture crystal formation, transform or/and in drying process, produce crystal formation, drying conditions is also had higher requirement.Compare with it, unformed RWJ 270201 disclosed by the invention has higher solvability (solubleness is three times of trihydrate in the water).
To sum up, it is low that unformed RWJ 270201 disclosed by the invention has overcome the crystalline state product solubility, is prone to mixed crystal in the preparation; Be prone to lose crystal water shortcomings such as crystalline substance take place to change; Disclosed unformed RWJ 270201 has simple, the favorable reproducibility of preparation technology, and to light, wet, thermally-stabilised, solvability is good; Be fit to long storage, be more suitable for advantages such as industrialized production.
Description of drawings
Fig. 1 is the x-ray diffractogram of powder spectrum of unformed RWJ 270201;
Fig. 2 is the infrared absorpting light spectra of unformed RWJ 270201.
Embodiment
Be better explanation technical scheme of the present invention, the spy provides following examples, but the present invention is not limited to this.Need to prove the preparation method of the anhydrous crystal forms RWJ 270201 that the present invention adopted, the preparation of reference CN101314579A disclosed method.
The reference implementation example
Embodiment 1
The preparation method of anhydrous crystal forms RWJ 270201:
Get bullion 35g (containing crystal water) and add methyl alcohol 5000mL stirring and dissolving, add SODIUM SULPHATE ANHYDROUS 99PCT 350g, stirred 5 hours; Left standstill 14 hours, the filtration drying agent is concentrated into and separates out a large amount of solids about 2000mL; Room temperature is placed 4 hours after-filtration and is got white solid, and 60 ℃ of dryings of vacuum get the 28g solid.Mp＞285 ℃ decomposition.
Embodiment 2
The preparation method of anhydrous crystal forms RWJ 270201:
Get bullion 11g (containing crystal water) and add ETHYLE ACETATE 2100mL, heat up 60 ℃ stirring and dissolving; Add anhydrous magnesium sulfate 100g, stirred the filtration drying agent 5 hours; Be concentrated into and separate out a large amount of solids about 1300mL, room temperature is placed 6 hours after-filtration and is got white solid, 60 ℃ of dryings of vacuum; Get the 9.4g solid, mp＞285 ℃ decomposition.
Embodiment 3
The preparation method of anhydrous crystal forms RWJ 270201:
Get bullion 11g (containing crystal water) and add methyl alcohol+ethanol 2100mL altogether, stirring and dissolving adds SODIUM SULPHATE ANHYDROUS 99PCT 100g, stirs 5 hours; The filtration drying agent is concentrated into 1500mL, separates out a large amount of solids, and room temperature was placed after 8 hours; Cross and filter white solid, 60 ℃ of dryings of vacuum get the 9.1g solid.Mp＞285 ℃ decomposition.
Preparation embodiment
Embodiment 1
The preparation method of unformed RWJ 270201:
10g anhydrous crystal forms RWJ 270201 is put into shredder (the German Fritsch Pulverisette6 of company shredder); The setting rotating speed is 400r/min, suspends 2min behind every 15min, behind the grinding 8h; Prepare white unformed RWJ 270201 fine powder 8.5g, yield 85%.The x-ray diffractogram of powder spectrum of unformed RWJ 270201 is seen shown in the accompanying drawing 1.
Embodiment 2
The preparation method of unformed RWJ 270201:
Use 10g anhydrous crystal forms RWJ 270201 for the preparation raw material, adopt thermostatic heating method, under 170 ℃ of conditions, keep 5h, reduce to room temperature then rapidly, prepare unformed RWJ 270201 9.5g, yield 95%.The x-ray diffractogram of powder spectrum of unformed RWJ 270201 is seen shown in the accompanying drawing 1.
Embodiment 3
The preparation method of unformed RWJ 270201:
(1) water dissolves the RWJ 270201 sample fully, adopts spray method to remove solvent rapidly again, prepares unformed RWJ 270201.The x-ray diffractogram of powder spectrum of unformed RWJ 270201 is seen shown in the accompanying drawing 1.
(2) with methyl alcohol the RWJ 270201 sample is dissolved fully, adopt spray method to remove solvent rapidly again, prepare unformed RWJ 270201.The x-ray diffractogram of powder spectrum of unformed RWJ 270201 is seen shown in the accompanying drawing 1.
(3) with ethanol the RWJ 270201 sample is dissolved fully, adopt spray method to remove solvent rapidly again, prepare unformed RWJ 270201.The x-ray diffractogram of powder spectrum of unformed RWJ 270201 is seen shown in the accompanying drawing 1.
(4) with Virahol the RWJ 270201 sample is dissolved fully, adopt spray method to remove solvent rapidly again, prepare unformed RWJ 270201.The x-ray diffractogram of powder spectrum of unformed RWJ 270201 is seen shown in the accompanying drawing 1.
Embodiment 4
Water and methanol mixed solvent (1: 1, v/v) the RWJ 270201 sample is dissolved fully, adopt spray method to remove solvent rapidly again, prepare unformed RWJ 270201.The x-ray diffractogram of powder spectrum of unformed RWJ 270201 is seen shown in the accompanying drawing 1.
Embodiment 5
Water and alcohol mixed solvent (1: 0.5, v/v) the RWJ 270201 sample is dissolved fully, adopt spray method to remove solvent rapidly again, prepare unformed RWJ 270201.The x-ray diffractogram of powder spectrum of unformed RWJ 270201 is seen shown in the accompanying drawing 1.
Embodiment 6
Water and isopropyl alcohol mixed solvent (1: 0.1, v/v) the RWJ 270201 sample is dissolved fully, adopt spray method to remove solvent rapidly again, prepare unformed RWJ 270201.The x-ray diffractogram of powder spectrum of unformed RWJ 270201 is seen shown in the accompanying drawing 1.
Embodiment 7
Water: methyl alcohol: acetone mixed solvent (1: 0.5: 0.3, v/v) the RWJ 270201 sample is dissolved fully, adopt spray method to remove solvent rapidly again, prepare unformed RWJ 270201.The x-ray diffractogram of powder spectrum of unformed RWJ 270201 is seen shown in the accompanying drawing 1.
The problem that needs explanation: have 22 kinds owing to can be used for preparing the single solvent of unformed RWJ 270201; Solvent combinations more than 2 kinds or 2 kinds has hundreds of; Every kind of solvent boiling point difference, different to RWJ 270201 sample dissolution degree, variate-values such as the envrionment temperature of its experiment, humidity, time all there is some difference property and constant interval scope when causing under the using the different solvents condition unformed RWJ 270201 of preparation.
FORMULATION EXAMPLE
Embodiment 1
Tablet 400mg.
Embodiment 2
The injection liquid that contains the unformed RWJ 270201 of 200mg.
Embodiment 3
The freeze-dried powder that contains the unformed RWJ 270201 of 200mg.
Conventional freeze-drying makes powder injection.
Claims (8)
1. unformed RWJ 270201 new crystal is characterized in that chemical purity and crystal formation purity all greater than 95% and do not contain crystal water or other recrystallisation solvents, and its structure is as shown in Figure 1; Its infrared absorption spectrum 3349,2964,2936,2877,2170,1654,1555,1460,1392,1334,1300,1261,1181,1147,1085,1036,993,963,783,757,695,594cm
-1The place has absorption peak to exist, wherein 2170,1036,695,594cm
-1For it presents the absorption peak position of unformed crystal formation characteristic.
2. the preparation method of the said unformed RWJ 270201 of claim 1 is characterized in that adopting physical method to destroy lattice, molecular transposition commentaries on classics crystalline substance or spraying drying and prepares unformed RWJ 270201;
Wherein said destruction lattice refers to: the anhydrous crystal forms RWJ 270201 is put into shredder, and the setting rotating speed is 300-500r/min, suspends 1-5min behind every 10-20min, behind the grinding 4-10h, prepares unformed RWJ 270201;
Described molecular transposition changes crystalline substance and refers to: the anhydrous crystal forms RWJ 270201 is adopted thermostatic heating method, under 120-250 ℃ of condition, keep 2-12h, reduce to room temperature then rapidly, prepare unformed RWJ 270201;
Described spraying drying refers to: the anhydrous crystal forms RWJ 270201 is mixed with single or mixed solvent, and the dissolving back adopts spray method to remove solvent rapidly fully, prepares unformed RWJ 270201;
Wherein said solvent is water, methyl alcohol, ethanol, acetone, n-propyl alcohol, Virahol, propyl carbinol, ETHYLE ACETATE, acetonitrile, THF, benzene, toluene, methylene dichloride, chloroform, normal hexane, hexanaphthene, dioxane, DMF, DMSO, ether, sherwood oil or pyridine.
3. the described preparation method of claim 2, single solvent wherein is water, methyl alcohol, ethanol or Virahol; Mixed solvent is a water: methyl alcohol, water: ethanol, water: Virahol; Or water: methyl alcohol: acetone.
4. the described preparation method of claim 3, wherein water: methyl alcohol, water: ethanol or water: the volume ratio of Virahol is 1: 0.1～1; Water: methyl alcohol: the volume ratio of acetone is 1: 0.1～1: 0.1～0.5.
5. a pharmaceutical composition is characterized in that said composition contains the described unformed RWJ 270201 new crystal of the claim 1 of treating significant quantity and pharmaceutically acceptable one or more pharmaceutical excipients.
6. the described compsn of claim 5, compsn wherein is tablet, capsule, injection liquid or freeze-dried powder.
7. the described compsn of claim 5, compsn wherein is injection liquid or the freeze-dried powder that contains the unformed RWJ 270201 of 100-400mg.
8. the described compsn of claim 5, wherein said compsn is tablet or the capsule that contains the unformed RWJ 270201 of 5-1000mg.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012101886523A CN102702033A (en) | 2012-06-11 | 2012-06-11 | Amorphous peramivir, preparation method thereof and medicinal composition |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012101886523A CN102702033A (en) | 2012-06-11 | 2012-06-11 | Amorphous peramivir, preparation method thereof and medicinal composition |
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| CN102702033A true CN102702033A (en) | 2012-10-03 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020173095A1 (en) | 2019-02-25 | 2020-09-03 | 广州南鑫药业有限公司 | Peramivir solution type inhalant and preparation method therefor |
| US20220380304A1 (en) * | 2019-07-03 | 2022-12-01 | Ckd Bio Corporation | Novel method for producing peramivir trihydrate, and water-based drying thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999033781A1 (en) * | 1997-12-17 | 1999-07-08 | Biocryst Pharmaceuticals, Inc. | Substituted cyclopentane and cyclopentene compounds useful as neuraminidase inhibitors |
| CN101314579A (en) * | 2007-05-30 | 2008-12-03 | 天津泰普药品科技发展有限公司 | Waterless Peramivir crystal and medicament composition thereof |
-
2012
- 2012-06-11 CN CN2012101886523A patent/CN102702033A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999033781A1 (en) * | 1997-12-17 | 1999-07-08 | Biocryst Pharmaceuticals, Inc. | Substituted cyclopentane and cyclopentene compounds useful as neuraminidase inhibitors |
| CN101314579A (en) * | 2007-05-30 | 2008-12-03 | 天津泰普药品科技发展有限公司 | Waterless Peramivir crystal and medicament composition thereof |
Non-Patent Citations (2)
| Title |
|---|
| POORAN CHAND ET AL.: "Systematic Structure-Based Design and Stereoselective Synthesis of Novel Multisubstituted Cyclopentane Derivatives with Potent Antiinfluenza Activity", 《JOURNAL OF THE MEDICINAL CHEMISTRY》, vol. 44, no. 25, 31 October 2001 (2001-10-31), pages 4379 - 4392 * |
| TOMOKO MINENO ET AL.: "Stereoselective Total Synthesis of Racemic BCX-1812 （RWJ-270201） for the Development of Neuraminidase Inhibitors as Anti-influenza Agents", 《JOURNAL OF ORGANIC CHEMSITRY》, vol. 68, 29 July 2003 (2003-07-29), pages 6591 - 6596 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020173095A1 (en) | 2019-02-25 | 2020-09-03 | 广州南鑫药业有限公司 | Peramivir solution type inhalant and preparation method therefor |
| US12226384B2 (en) | 2019-02-25 | 2025-02-18 | Guangzhou Nanxin Pharmaceutical Co., Ltd. | Peramivir solution type inhalant and preparation method therefor |
| US20220380304A1 (en) * | 2019-07-03 | 2022-12-01 | Ckd Bio Corporation | Novel method for producing peramivir trihydrate, and water-based drying thereof |
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