WO2011016044A1 - Novel polymorphs of adefovir dipivoxil - Google Patents
Novel polymorphs of adefovir dipivoxil Download PDFInfo
- Publication number
- WO2011016044A1 WO2011016044A1 PCT/IN2009/000440 IN2009000440W WO2011016044A1 WO 2011016044 A1 WO2011016044 A1 WO 2011016044A1 IN 2009000440 W IN2009000440 W IN 2009000440W WO 2011016044 A1 WO2011016044 A1 WO 2011016044A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- adefovir dipivoxil
- crystalline form
- pharmaceutical composition
- crystalline
- adefovir
- Prior art date
Links
- WOZSCQDILHKSGG-UHFFFAOYSA-N adefovir depivoxil Chemical compound N1=CN=C2N(CCOCP(=O)(OCOC(=O)C(C)(C)C)OCOC(=O)C(C)(C)C)C=NC2=C1N WOZSCQDILHKSGG-UHFFFAOYSA-N 0.000 title claims abstract description 42
- 229960003205 adefovir dipivoxil Drugs 0.000 title claims abstract description 41
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000000034 method Methods 0.000 claims abstract description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 239000000203 mixture Substances 0.000 claims abstract description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 claims description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 239000002775 capsule Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 239000000725 suspension Substances 0.000 claims description 2
- 239000003826 tablet Substances 0.000 claims description 2
- 239000007787 solid Substances 0.000 abstract description 6
- 239000000706 filtrate Substances 0.000 abstract description 3
- -1 filtered Substances 0.000 abstract 1
- 238000000634 powder X-ray diffraction Methods 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 4
- 238000004566 IR spectroscopy Methods 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 229940123527 Nucleotide reverse transcriptase inhibitor Drugs 0.000 description 1
- 208000005074 Retroviridae Infections Diseases 0.000 description 1
- 229960001997 adefovir Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004682 monohydrates Chemical group 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000001144 powder X-ray diffraction data Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65616—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system having three or more than three double bonds between ring members or between ring members and non-ring members, e.g. purine or analogs
Definitions
- the present invention provides novel crystalline form of adefovir dipivoxil, process for its preparation and pharmaceutical composition comprising it.
- Adefovir dipivoxil is a known nucleotide reverse transcriptase inhibitor used in clinic for the treatment of retrovirus infections, in particular HIV and HBV infections.
- Adefovir is represented by the following structure:
- Patent No. 5,663,159 discloses a patent No.
- Polymorphism is defined as "the ability of a substance to exist as two or more crystalline phases that have different arrangement and /or conformations of the molecules in the crystal Lattice.
- polymorphs are different crystalline forms of the same pure substance in which the molecules have different arrangements and / or different configurations of the molecules.
- Different polymorphs may differ in their physical properties such as melting point, solubility, X-ray diffraction patterns, etc. Although those differences disappear once the compound is dissolved, they can appreciably influence pharmaceutically relevant properties of the solid form, such as handling properties, dissolution rate and stability. Such properties can significantly influence the processing, shelf life, and commercial acceptance of a polymorph.
- Polymorphic forms of a compound can be distinguished in the laboratory by analytical methods such as X-ray diffraction (XRD), Differential Scanning Calorimetry (DSC) and Infrared spectrometry (IR).
- XRD X-ray diffraction
- DSC Differential Scanning Calorimetry
- IR Infrared spectrometry
- Solvent medium and mode of crystallization play very important role in obtaining a crystalline form over the other.
- Adefovir dipivoxil can exist in different polymorphic forms, which differ from each other in terms of stability, physical properties, spectral data and methods of preparation.
- US Patent No. 6,451,340 disclosed various polymorphic forms, crystalline form 1 (characterized by an x-ray powder diffraction patterns having peaks expressed as 2 ⁇ at about 6.9 degrees), form 2 (characterized by an x-ray powder diffraction patterns having peaks expressed as 2 ⁇ at about 9.6, 18.3,
- form 3 characterized by an x-ray powder diffraction patterns having peaks expressed as 2 ⁇ at about 8.1 , 19.4, 25.4 and 30.9 degrees
- form 4 characterized by an x-ray powder diffraction patterns having peaks expressed as 2 ⁇ at about 9.8, 15.2, 26.3 and 31.7 degrees
- WO Patent Publication No. 2009/015892 disclosed various polymorphic forms, monohydrate form A and form B of adefovir dipivoxil.
- An object of the present invention is to provide a novel crystalline form of adefovir dipivoxil, process for their preparation and pharmaceutical composition comprising it.
- the present invention provided a novel crystalline form of adefovir dipivoxil designated as form H1 characterized by peaks in the powder x-ray diffraction spectrum having 2 ⁇ angle positions at about 4.2, 8.5, 17.1 , 21.4 and 25.8 ⁇ 0.2 degrees.
- the present invention provides a process for preparing adefovir dipivoxil crystalline from H1 , which comprises:
- step (b) adding water to the solution obtained in step (a);
- the present invention provides a pharmaceutical composition
- a pharmaceutical composition comprising crystalline form H1 of adefovir dipivoxil and a pharmaceutically acceptable excipient.
- Figure 1 is X-ray powder diffraction spectrum of adefovir dipivoxil crystalline form H1.
- X-ray powder diffraction spectrum was measured on a bruker axs D8 advance X-ray powder diffractometer having a copper-K ⁇ radiation. Approximately 1gm of sample was gently flattered on a sample holder and scanned from 2 to 50 degrees two-theta, at 0.02 degrees to theta per step and a step of 10.4 seconds. The sample was simply placed on the sample holder. The sample was rotated at 30 rpm at a voltage 40 KV and current 35 mA.
- a novel crystalline form of adefovir dipivoxil designated as form H1 characterized by peaks in the powder x-ray diffraction spectrum having 2 ⁇ angle positions at about 4.2, 8.5, 17.1 , 21.4 and 25.8 ⁇ 0.2 degrees.
- the powdered x-ray diffractogram (PXRD) of adefovir dipivoxil crystalline form H1 is shown in figure 1.
- the crystalline form H1 may be identified and differentiated from the known crystalline forms by its characteristic PXRD pattern.
- peak at 32.8 ⁇ 0.2 degrees 2 ⁇ is absent in the PXRD of the crystalline form H1 of the present invention, but is present in the PXRD of the crystalline Form 2 of adefovir dipivoxil disclosed in the U. S. Patent No. 6,451 ,340.
- the water content of the novel crystalline form, form H1 is in range 6.0 to 7.5 by weight.
- a process for the preparation of adefovir dipivoxil crystalline form H1 which comprises:
- step (b) adding water to the solution obtained in step (a);
- the ketonic solvent used in step (a) may be a solvent or mixture of solvents selected from the group consisting of a methyl ethyl ketone, acetone, methyl isobutyl ketone and methyl isopropyl ketone.
- Preferable ketonic solvent is methyl ethyl ketone.
- isolation of adefovir dipivoxil crystalline from H1 may be performed by conventional techniques such as centrifugation and filtration.
- the temperature at which slurrying is carried out is not critical and the slurrying may conveniently be carried out at room temperature.
- a pharmaceutical composition comprising adefovir dipivoxil crystalline from H1 and a pharmaceutically acceptable excipient.
- compositions may be in the form of tablets, capsules, solutions, suspensions or emulsions.
- the invention will now be further described by the following examples, which are illustrative rather than limiting.
- Adefovir dipivoxil (10 gm) was dissolved in a mixture of N- methylpyrrolidone (60 ml) and methyl ethyl ketone (40 ml). The reaction mixture was stirred for 30 minutes at room temperature and filtered. To the filtrate was added water (1600 ml) and stirred for 12 hours. The solid obtained was collected by filtration and the solid was washed with water, and then dried at 35 to 40 0 C under vacuum for 2 hours to obtain 9.3 gm of adefovir dipivoxil crystalline form Hl Example 2
- Adefovir dipivoxil (5 gm) was dissolved in a mixture of N- methylpyrrolidone (30 ml) and methyl isobutyl ketone (25 ml). The reaction mixture was stirred for 30 minutes at room temperature and filtered. To the filtrate was added water (800 ml) and stirred for 10 hours, filtered. The solid obtained washed with water and dried at 35 to 40 0 C under vacuum for 2 hours to obtain 4.2 gm of adefovir dipivoxil crystalline form H1.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention provides novel crystalline form of adefovir dipivoxil, process for its preparation and pharmaceutical composition comprising it. Thus, for example, adefovir dipivoxil was dissolved in a mixture of N-methylpyrrolidone and methyl ethyl ketone, filtered, water was added to the filtrate, stirred for 12 hours and separated solid was filtered, washed with water and dried to give adefovir dipivoxil crystalline form H1.
Description
NOVEL POLYMORPHS OF ADEFOVIR DIPIVOXIL
FIELD OF THE INVENTION
The present invention provides novel crystalline form of adefovir dipivoxil, process for its preparation and pharmaceutical composition comprising it.
BACKGROUND OF THE INVENTION
Adefovir dipivoxil is a known nucleotide reverse transcriptase inhibitor used in clinic for the treatment of retrovirus infections, in particular HIV and HBV infections.
Adefovir is represented by the following structure:
Patent No. 5,663,159.
Polymorphism is defined as "the ability of a substance to exist as two or more crystalline phases that have different arrangement and /or conformations of the molecules in the crystal Lattice. Thus, in the strict sense, polymorphs are different crystalline forms of the same pure substance in which the molecules have different arrangements and / or different configurations of the molecules". Different polymorphs may differ in their physical properties such as melting point, solubility, X-ray diffraction patterns, etc. Although those differences disappear once the compound is dissolved, they can appreciably influence pharmaceutically relevant properties of the solid form, such as handling properties, dissolution rate and stability. Such properties can significantly influence the processing, shelf life, and commercial acceptance of a polymorph. It is therefore important to investigate all solid forms of a drug, including all polymorphic forms, and to determine the stability, dissolution and flow properties
of each polymorphic form. Polymorphic forms of a compound can be distinguished in the laboratory by analytical methods such as X-ray diffraction (XRD), Differential Scanning Calorimetry (DSC) and Infrared spectrometry (IR).
Solvent medium and mode of crystallization play very important role in obtaining a crystalline form over the other.
Adefovir dipivoxil can exist in different polymorphic forms, which differ from each other in terms of stability, physical properties, spectral data and methods of preparation.
US Patent No. 6,451,340 disclosed various polymorphic forms, crystalline form 1 (characterized by an x-ray powder diffraction patterns having peaks expressed as 2Θ at about 6.9 degrees), form 2 (characterized by an x-ray powder diffraction patterns having peaks expressed as 2Θ at about 9.6, 18.3,
22.0 and 32.8 degrees), form 3 (characterized by an x-ray powder diffraction patterns having peaks expressed as 2Θ at about 8.1 , 19.4, 25.4 and 30.9 degrees) and form 4 (characterized by an x-ray powder diffraction patterns having peaks expressed as 2Θ at about 9.8, 15.2, 26.3 and 31.7 degrees) of adefovir dipivoxil.
US Patent No. 7,417,036 disclosed a crystalline adefovir dipivoxil
(characterized by an x-ray powder diffraction patterns having peaks expressed as 2Θ at about 3.60, 7.28, 15.08, 17.24, 17.96, 20.12 and 22.24 degrees and further characterized by a DSC thermogram an endothermic peak at about
94.50C).
Processes for the preparation of amorphous adefovir dipivoxil were disclosed in CN 1670025, CN 1621408 and CN 1847252.
WO Patent Publication No. 2009/015892 disclosed various polymorphic forms, monohydrate form A and form B of adefovir dipivoxil.
Thus there is a need for stable and reproducible crystalline forms of adefovir dipivoxil.
We have discovered novel crystalline form of adefovir dipivoxil. The novel form has been found to be stable over the time and reproducible and so, suitable for pharmaceutical preparations.
An object of the present invention is to provide a novel crystalline form of adefovir dipivoxil, process for their preparation and pharmaceutical composition comprising it.
SUMMARY OF THE INVENTION
In one aspect, the present invention provided a novel crystalline form of adefovir dipivoxil designated as form H1 characterized by peaks in the powder x-ray diffraction spectrum having 2Θ angle positions at about 4.2, 8.5, 17.1 , 21.4 and 25.8 ± 0.2 degrees.
In another aspect, the present invention provides a process for preparing adefovir dipivoxil crystalline from H1 , which comprises:
a) preparing a solution of adefovir dipivoxil in a mixture of N- methylpyrrolidone and a ketonic solvent;
b) adding water to the solution obtained in step (a);
c) slurring the reaction mass obtained in step (b); and
d) isolating adefovir dipivoxil crystalline from H1.
In yet another aspect, the present invention provides a pharmaceutical composition comprising crystalline form H1 of adefovir dipivoxil and a pharmaceutically acceptable excipient.
BRIEF DESCRIPTION OF THE DRAWING
Figure 1 is X-ray powder diffraction spectrum of adefovir dipivoxil crystalline form H1.
X-ray powder diffraction spectrum was measured on a bruker axs D8 advance X-ray powder diffractometer having a copper-Kα radiation. Approximately 1gm of sample was gently flattered on a sample holder and scanned from 2 to 50 degrees two-theta, at 0.02 degrees to theta per step and a step of 10.4 seconds. The sample was simply placed on the sample holder. The sample was rotated at 30 rpm at a voltage 40 KV and current 35 mA.
DETAILED DESCRIPTION OF THE INVENTION
According to one aspect of the present invention, there is provided a novel crystalline form of adefovir dipivoxil designated as form H1 characterized by peaks in the powder x-ray diffraction spectrum having 2Θ angle positions at about 4.2, 8.5, 17.1 , 21.4 and 25.8 ± 0.2 degrees. The powdered x-ray diffractogram (PXRD) of adefovir dipivoxil crystalline form H1 is shown in figure 1.
The crystalline form H1 may be identified and differentiated from the known crystalline forms by its characteristic PXRD pattern. Thus, for example, peak at 32.8 ± 0.2 degrees 2Θ is absent in the PXRD of the crystalline form H1 of the present invention, but is present in the PXRD of the crystalline Form 2 of adefovir dipivoxil disclosed in the U. S. Patent No. 6,451 ,340.
The water content of the novel crystalline form, form H1 is in range 6.0 to 7.5 by weight.
According to another aspect of the present invention, there is provided a process for the preparation of adefovir dipivoxil crystalline form H1 , which comprises:
a) preparing a solution of adefovir dipivoxil in a mixture of N- methylpyrrolidone and a ketonic solvent;
b) adding water to the solution obtained in step (a);
c) slurring the reaction mass obtained in step (b); and
d) isolating adefovir dipivoxil crystalline from H1.
The ketonic solvent used in step (a) may be a solvent or mixture of solvents selected from the group consisting of a methyl ethyl ketone, acetone, methyl isobutyl ketone and methyl isopropyl ketone. Preferable ketonic solvent is methyl ethyl ketone.
The isolation of adefovir dipivoxil crystalline from H1 may be performed by conventional techniques such as centrifugation and filtration.
The temperature at which slurrying is carried out is not critical and the slurrying may conveniently be carried out at room temperature.
According to another aspect of the present invention, there is provided a pharmaceutical composition comprising adefovir dipivoxil crystalline from H1 and a pharmaceutically acceptable excipient.
The pharmaceutical compositions may be in the form of tablets, capsules, solutions, suspensions or emulsions. The invention will now be further described by the following examples, which are illustrative rather than limiting.
EXAMPLES
Preparation of adefovir dipivoxil crystalline form H1
Example 1
Adefovir dipivoxil (10 gm) was dissolved in a mixture of N- methylpyrrolidone (60 ml) and methyl ethyl ketone (40 ml). The reaction mixture was stirred for 30 minutes at room temperature and filtered. To the filtrate was added water (1600 ml) and stirred for 12 hours. The solid obtained was collected by filtration and the solid was washed with water, and then dried at 35 to 400C under vacuum for 2 hours to obtain 9.3 gm of adefovir dipivoxil crystalline form Hl Example 2
Adefovir dipivoxil (5 gm) was dissolved in a mixture of N- methylpyrrolidone (30 ml) and methyl isobutyl ketone (25 ml). The reaction mixture was stirred for 30 minutes at room temperature and filtered. To the filtrate was added water (800 ml) and stirred for 10 hours, filtered. The solid obtained washed with water and dried at 35 to 400C under vacuum for 2 hours to obtain 4.2 gm of adefovir dipivoxil crystalline form H1.
Claims
1 . Adefovir dipivoxil crystalline form H1 , characterized by an x-ray powder diffractogram having peaks expressed as 2Θ angle positions at about 4.2,
8.5, 17.1 , 21.4 and 25.8 ± 0.2 degrees.
2. Adefovir dipivoxil crystalline form H1 , characterized by an x-ray powder diffractogram as shown in figure 1.
3. A process for the preparation of adefovir dipivoxil crystalline form H1 as defined in claim 1 , which comprises:
a. preparing a solution of adefovir dipivoxil in a mixture of N- methylpyrrolidone and a ketonic solvent;
b. adding water to the solution obtained in step (a);
c. slurring the reaction mass obtained in step (b); and
d. isolating adefovir dipivoxil crystalline from H1.
4. The process as claimed in claim 4, wherein the ketonic solvent used in step (a) is a solvent or mixture of solvents selected from methyl ethyl ketone, acetone, methyl isobutyl ketone and methyl isopropyl ketone.
5. The process as claimed in claim 5, wherein the ketonic solvent used in step (a) is methyl ethyl ketone.
6. A pharmaceutical composition comprising a crystalline form H1 of adefovir dipivoxil and a pharmaceutically acceptable excipient.
7. The pharmaceutical composition as claimed in claim 7, wherein the pharmaceutical composition is used in the form of tablets, capsules, solutions, suspensions or emulsions
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IN2009/000440 WO2011016044A1 (en) | 2009-08-03 | 2009-08-03 | Novel polymorphs of adefovir dipivoxil |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/IN2009/000440 WO2011016044A1 (en) | 2009-08-03 | 2009-08-03 | Novel polymorphs of adefovir dipivoxil |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2011016044A1 true WO2011016044A1 (en) | 2011-02-10 |
Family
ID=43544001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IN2009/000440 WO2011016044A1 (en) | 2009-08-03 | 2009-08-03 | Novel polymorphs of adefovir dipivoxil |
Country Status (1)
| Country | Link |
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| WO (1) | WO2011016044A1 (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1903863A (en) * | 2006-07-28 | 2007-01-31 | 齐鲁制药有限公司 | Preparation method of adefovir dipivoxil crystal |
| CN1935818A (en) * | 2006-09-22 | 2007-03-28 | 闫敬武 | Adefovir dipivoxil novel crystallinestate, crystalline state composition, and itspreparing method and use |
| CN101343290A (en) * | 2008-05-24 | 2009-01-14 | 广东肇庆星湖生物科技股份有限公司 | Preparation method for adefovir dipivoxil ester waterless crystallization article, prepared adefovir dipivoxil ester waterless crystallization article and uses thereof |
| WO2009015892A1 (en) * | 2007-08-02 | 2009-02-05 | Solmag S.P.A. | Adefovir dipivoxil crystalline monohydrate form |
-
2009
- 2009-08-03 WO PCT/IN2009/000440 patent/WO2011016044A1/en active Application Filing
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1903863A (en) * | 2006-07-28 | 2007-01-31 | 齐鲁制药有限公司 | Preparation method of adefovir dipivoxil crystal |
| CN1935818A (en) * | 2006-09-22 | 2007-03-28 | 闫敬武 | Adefovir dipivoxil novel crystallinestate, crystalline state composition, and itspreparing method and use |
| WO2009015892A1 (en) * | 2007-08-02 | 2009-02-05 | Solmag S.P.A. | Adefovir dipivoxil crystalline monohydrate form |
| CN101343290A (en) * | 2008-05-24 | 2009-01-14 | 广东肇庆星湖生物科技股份有限公司 | Preparation method for adefovir dipivoxil ester waterless crystallization article, prepared adefovir dipivoxil ester waterless crystallization article and uses thereof |
Non-Patent Citations (2)
| Title |
|---|
| DATABASE WPI Derwent World Patents Index; AN 2007-604594, THOMPSON DATABASE * |
| DATABASE WPI Derwent World Patents Index; AN 2009-E31810, THOMPSON * |
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