WO2016016766A2 - A process for the preparation of isavuconazonium or its salt thereof - Google Patents
A process for the preparation of isavuconazonium or its salt thereof Download PDFInfo
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- WO2016016766A2 WO2016016766A2 PCT/IB2015/055511 IB2015055511W WO2016016766A2 WO 2016016766 A2 WO2016016766 A2 WO 2016016766A2 IB 2015055511 W IB2015055511 W IB 2015055511W WO 2016016766 A2 WO2016016766 A2 WO 2016016766A2
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- isavuconazonium
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- DDFOUSQFMYRUQK-RCDICMHDSA-N C[C@H]([C@](C[n]1ncnc1)(c(cc(cc1)F)c1F)O)c1nc(-c(cc2)ccc2C#N)c[s]1 Chemical compound C[C@H]([C@](C[n]1ncnc1)(c(cc(cc1)F)c1F)O)c1nc(-c(cc2)ccc2C#N)c[s]1 DDFOUSQFMYRUQK-RCDICMHDSA-N 0.000 description 1
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- C07—ORGANIC CHEMISTRY
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- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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Abstract
The present invention relates to a process for the preparation of stable Isavuconazonium or its salt thereof. In particular of the present invention relates to process for the preparing of isavuconazonium sulfate, Isavuconazonium iodide hydrochloride and Boc-protected isavuconazonium iodide has purity more than 90%. The process is directed to preparation of solid amorphous form of isavuconazonium sulfate, isavuconazonium iodide hydrochloride and Boc-protected isavuconazonium iodide. The present invention process of Isavuconazonium or its salt thereof is industrially feasible, simple and cost effective to manufacture of isavuconazonium sulfate with the higher purity and better yield.
Description
A PROCESS FOR THE PREPARATION OF ISAVUCONAZONIUM OR ITS
SALT THEREOF
Field of Invention
The present invention relates to a process for the preparation of stable Isavuconazonium or its salt thereof. In particular of the present invention relates to process for the preparing of isavuconazonium sulfate, Isavuconazonium iodide hydrochloride and Boc -protected isavuconazonium iodide has purity more than 90%. The process is directed to preparation of solid amorphous form of isavuconazonium sulfate, isavuconazonium iodide hydrochloride and Boc -protected isavuconazonium iodide. The present invention process of Isavuconazonium or its salt thereof is industrially feasible, simple and cost effective to manufacture of isavuconazonium sulfate with the higher purity and better yield.
Background of the invention
Isavuconazonium sulfate is chemically known l-[[N-methyl-N-3-[(methylamino) acetoxymethyl]pyridin-2-yl] carbamoyloxy]ethyl-l-[(2R,3R)-2-(2,5-difluorophenyl)-2- hydroxy-3-[4-(4-cyanophenyl)thiazol-2-yl]butyl]-lH-[l,2,4]-triazo-4-ium Sulfate and is structurally represented by formula (I):
Formula I
Isavuconazonium sulfate (BAL8557) is indicated for the treatment of antifungal infection. Isavuconazonium sulfate is a prodrug of Isavuconazole (BAL4815), which is chemically known 4-{2-[(lR,2R)-(2,5-Difluorophenyl)-2-hydroxy-l-methyl-3-(lH-l ,2,4- triazol-l-yl)propyl]-l ,3-thiazol-4-yl}benzonitrile compound of Formula II
Formula II
US Ppatent No. 6,812,238 (referred to herein as '238); 7,189,858 (referred to herein as '858); 7,459,561 (referred to herein as '561) describe Isavuconazonium and its process for the preparation thereof.
The US Pat. '238 patent describes the process of preparation of Isavuconazonium chloride hydrochloride.
The US Pat. '238 described the process for the Isavuconazonium chloride hydrochloride, involves the condensation of Isavuconazole and [N-methyl-N-3((tert-butoxycarbonyl methylamino) acetoxymethyl) pyridine-2-yl]carbamic acid 1 -chloro-ethyl ester. The prior art reported process require almost 15-16 hours, whereas the present invention process requires only 8-10 hours. Inter alia prior art reported process requires too many step to prepare isavuconazonium sulfate, whereas the present invention process requires fewer steps.
Moreover, the US Pat. '238 describes the process for the preparation Isavuconazonium hydrochloride, which may be used as the key intermediate for the synthesis of isavuconazonium sulfate, compound of formula I. There are several drawbacks in the said process, which includes the use of anionic resin to prepare Isavuconazonium chloride
hydrochloride, consequently it requires multiple time lyophilization, which makes the said prior art process industrially, not feasible.
The inventors of the present invention surprisingly found that Isavuconazonium or a pharmaceutically acceptable salt thereof in yield and purity could be prepared by using substantially pure intermediates in suitable solvent.
Thus, an object of the present invention is to provide simple, cost effective and industrially feasible processes for manufacture of isavuconazonium sulfate. Inventors of the present invention surprisingly found that isavuconazonium sulfate prepared from isavuconazonium iodide hydrochloride, provides enhanced yield as well as purity.
Summary of the Invention
The present invention provides a solid amorphous form of isavuconazonium sulfate, compound of Formula
Formula I
The present invention provides the process for the preparation of a solid amorphous form of isavuconazonium sulfate compound of Formula I, which includes contacting isavuconazonium iodide hydrochloride compound of Formula IA with anion exchange resin in the suitable solvent and followed by isolation of isavuconazonium sulfate compound of Formula I in the suitable solvent.
In another aspect, the present invention provides isavuconazonium sulfate compound of Formula I, has purity more than 94%, when measured by HPLC.
The present invention also provides a solid amorphous form of isavuconazonium iodide hydrochloride, compound of Formula IA,
Formula IA
In another aspect, the present invention provides isavuconazonium iodide hydrochloride compound of Formula IA, has purity more than 90%, when measured by HPLC.
The present invention provides the process for the preparation of a solid amorphous form of isavuconazonium iodide hydrochloride compound of Formula IA, which includes steps of reacting isavuconazole compound of formula (II) or salt thereof with [N-methyl-N- 3((tert-butoxycarbonyl methylamino) acetoxymethyl) pyridine-2-yl]carbamic acid 1- chloro-ethyl ester or salt thereof compound of formula (III) in presence of iodide salt, in the suitable solvent to obtain compound of Boc -protected isavuconazonium iodide compound of formula (IV). Deprotection of Boc -protected isavuconazonium iodide compound of formula (IV) with hydrochloric acid in suitable solvent to obtain isavuconazonium iodide hydrochloride compound of Formula IA.
Formula (III) Formula (III)
In another aspect, the present invention provides a solid amorphous form of Boc- isavuconazonium iodide com ound of formula (IV)
Formula IV
In another aspect, the present invention provides solid amorphous form of Boc- isavuconazonium iodide, has purity more than 90%, when measured by HPLC.
Brief Description of the Drawings
Figure 1 shows an illustrative example of X-ray powder diffraction pattern of solid amorphous form of isavuconazonium sulfate.
Figure 2 shows an illustrative example of differential scanning calorimetry thermogram of solid amorphous form of isavuconazonium sulfate.
Figure 3 shows an illustrative example of thermogravimetric analysis curve of solid amorphous form of isavuconazonium sulfate
Figure 4 shows an illustrative example of X-ray powder diffraction pattern of solid amorphous form of isavuconazonium iodide hydrochloride.
Figure 5 shows an illustrative example of differential scanning calorimetry thermogram of solid amorphous form of isavuconazonium iodide hydrochloride.
Figure 6 shows an illustrative example of thermogravimetric analysis curve of solid amorphous form of isavuconazonium iodide hydrochloride
Figure 7 shows an illustrative example of X-ray powder diffraction pattern of solid amorphous form of Boc-isavuconazonium iodide.
Figure 8 shows an illustrative example of differential scanning calorimetry thermogram of solid amorphous form of Boc-isavuconazonium iodide.
Figure 9 shows an illustrative example of thermogravimetric analysis curve of solid amorphous form of Boc-isavuconazonium iodide
Description of the Invention
For purposes of the present invention, the following terms are defined below.
The X-ray diffraction powder patterns of the present invention were obtained using a Bruker or PANalytical export Pro Powder X-ray Diffractometer at Cu Ka radiation, has the wavelength 1.54 A.
As used herein, the term "reference standard" refers to a compound that may be used both for quantitative and qualitative analysis of an active pharmaceutical ingredient. A reference marker" is used only for qualitative analysis, while a reference standard may be used for quantitative or qualitative analysis, or both. Hence, a reference marker is a subset of a reference standard, and is included within the definition of a reference standard.
In one aspect of the present invention provides a solid amorphous form of isavuconazonium sulfate, compound of Formula I,
Formula I
In another aspect, the present invention provides a solid amorphous form of isavuconazonium sulfate is characterized by its X-ray powder diffraction pattern substantially as shown in Figure 1, differential scanning calorimetry thermogram as shown in Figure 2 and Thermogavimetric Analysis (TGA) as shown in Figure 3.
The solid amorphous form of isavuconazonium sulfate obtained according to present invention was stored at 25 °C for a period of 3 months and no conversion in the polymorphic form was observed.
In another aspect, the present invention provides a solid amorphous form isavuconazonium sulfate, compound of Formula I, has purity more than 94 % by as measured HPLC.
In one of the embodiment the isavuconazonium Sulfate obtained by the process of present invention shown stability under standard condition of stability as described in United States Pharmacopoeia 2014.
In another aspect, the present invention provides a process for the preparation of isavuconazonium sulfate, compound of Formula I,
Formula I
which includes steps of;
a) contacting isavuconazonium iodide hydrochloride compound of Formula IA
Formula IA
with anion exchange resin in the suitable solvent,
b) isolating isavuconazonium sulfate in the suitable solvent.
Suitable solvent is selected from the group comprising one or more of alcohol, halogenated solvent, acetates, ether, hydrocarbon, water or mixture thereof. The alcohol such as methanol, ethanol, isopropyl alcohol and the like; the halogenated solvent such dichlorome thane; the ether such as methyl tert-butyl ether, ethyl tert-butyl ether, diethyl ether, di-tert-butyl ether and the like; the amides such as dimethyl acetamide and dimethyl formamide and the like; the acetate such as ethyl acetate, propyl acetate, butyl acetate and the like; hydrocarbon such as toluene, n-hexane, benzene, heptane and the like.
The anion exchange resin includes is selected from the group comprising Diaion™ SA10A, Diaion™ SA11A, Diaion™ SA12A, Diaion™ NSA100, Diaion™ PA308, PA306, Amberjet 4000 CI, Amberjet 4400 CI and Amberjet 4600 CI.
In one aspect, the present invention provides a solid amorphous form of isavuconazonium iodide hydrochloride, compound of Formula IA.
Formula IA
In another aspect, the present invention provides isavuconazonium iodide hydrochloride, has purity more than 90 %, as measured HPLC.
In another aspect, the present invention provides a solid amorphous form of isavuconazonium iodide hydrochloride is characterized by its X-ray powder diffraction pattern substantially as shown in Figure 4, differential scanning calorimetry thermogram as shown in Figure 5 and Thermogavimetric Analysis (TGA) as shown in Figure 6.
The solid amorphous form of isavuconazonium iodide hydrochloride obtained according to present invention was stored at 25 °C for a period of 3 months and no conversion in the polymorphic form was observed.
In one aspect, the present invention provides a solid amorphous form of Boc- isavuconazonium iodide compound of formula (IV)
Formula IV
In another aspect, the present invention provides a solid amorphous form of Boc- isavuconazonium iodide is characterized by its X-ray powder diffraction pattern substantially as shown in Figure 7, differential scanning calorimetry thermogram as shown in Figure 8 and Thermogavimetric Analysis (TGA) as shown in Figure 9.
The solid amorphous form of Boc -isavuconazonium iodide obtained according to present invention was stored at 25 °C for a period of 3 months and no conversion in the polymorphic form was observed.
In another aspect, the present invention provides a solid amorphous form of Boc- isavuconazonium iodide, has purity more than 90 %, as measured HPLC.
In another aspect, the present invention provides a process for the preparation of isavuconazonium iodide hydrochloride compound of Formula IA,
Formula IA
which includes steps of
a) reacting isavuconazole comp r salt thereof
Formula II
with [N-methyl-N-3((tert-butoxycarbonylmethylamino)acetoxymethyl)pyridine- 2-yl] carbamic acid 1 -chloro-ethyl ester or salt thereof compound of formula (III)
Formula III
in presence of iodide salt, in the suitable solvent to obtain Boc -protected isavuconazonium iodide com ound of formula (IV)
Formula IV
b) deprotecting Boc -protected isavuconazonium iodide compound of formula (IV) with hydrochloric acid in suitable solvent to obtain isavuconazonium iodide hydrochloride compound of Formula IA.
Suitable solvent used in the step (a) is selected from the group comprising one or more of nitrile, ether, amides, alcohol, acetates, hydrocarbon, water or mixture thereof. The nitriles such as acetonitrile and propionitrile and the like; the ether such as methyl tert- butyl ether, ethyl tert-butyl ether, diethyl ether, di-tert-butyl ether, dioxane and the like; the amides such as dimethyl acetamide and dimethyl formamide and the like; the alcohol such as methanol, ethanol, isopropyl alcohol and the like; the acetate such as ethyl acetate, propyl acetate, butyl acetate and the like; hydrocarbon such as toluene, n-hexane, benzene, heptane and the like;
Suitable solvent used in the step (b) is selected from the group comprising one or more of acetates, alcohols, amides, ether, chlorinated solvents, water or mixture thereof. The acetate such as ethyl acetate, propyl acetate, butyl acetate and the like; the alcohol such as methanol, ethanol, isopropyl alcohol and the like; the ether such as methyl tert-butyl ether, ethyl tert-butyl ether, diethyl ether, di-tert-butyl ether, dioxane and the like; the amides such as dimethyl acetamide and dimethyl formamide and the like; chlorinated solvents such as dichloromethane, chloroform, chlorobenzene and the like.
The used hydrochloric gas is purged in suitable solvent, wherein the percentage of hydrochloric acid in the suitable solvent is 12 to 20 % w/v.
Iodide salt used for the reaction includes but is not limited to potassium iodide and sodium iodide.
The process of the present invention is depicted in the following scheme:
Formula I
Formula-IA
The present invention is further illustrated by the following example, which does not limit the scope of the invention. Certain modifications and equivalents will be apparent to those skilled in the art and are intended to be included within the scope of the present application.
Examples
Example-1: Synthesis of l-[[N-methyl-N-3-[(t-butoxycarbonylmethylamino) acetoxymethyl]pyridin-2-yl]carbamoyloxy]ethyl-l-[(2R,3R)-2-(2,5-difluorophenyl)-2- hydroxy-3 - [4-(4-cyanophenyl)thiazol-2-yl]butyl] - 1 H-[ 1 ,2,4] -triazo-4-ium iodide
Isavuconazole (20 g) and [N-methyl-N-3((tert-butoxycarbonylmethylamino)acetoxy methyl)pyridine-2-yl]carbamic acid 1 -chloro-ethyl ester (24.7 g) were dissolved in acetonitrile (200ml). The reaction mixture was stirred to add potassium iodide (9.9 g). The reaction mixture was stirred at 47-50°C for 10-13 hour. The reaction mixture was cooled to room temperature. The reaction mass was filtered through celite bed and washed acetonitrile. Residue was concentrated under reduced pressure to give the crude solid product (47.7 g). The crude product was purified by column chromatography to get its pure iodide form (36.5 g).
Yield: 84.5 %
HPLC Purity: 87%
Mass: m/z 817.4 (M- 1)+
Example-2: Synthesis of l-[[N-methyl-N-3-[(methylamino)acetoxymethyl]pyridin-2-yl] carbamoyloxy]ethyl-l-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl) thiazol-2-yl]butyl]-lH-[l ,2,4]-triazo-4-ium iodide hydrochloride l-[[N-methyl-N-3-[(t-butoxycarbonylmethylamino)acetoxymethyl]pyridin-2-yl] carbamoyloxy]ethyl-l-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl) thiazol-2-yl]butyl]-lH-[l ,2,4]-triazo-4-ium iodide (36.5 g) was dissolved in ethyl acetate (600 ml). The reaction mixture was cooled to -5 to 0 °C. The ethyl acetate hydrochloride (150 ml) solution was added to reaction mixture. The reaction mixture was stirred for 4-5 hours at room temperature. The reaction mixture was filtered and obtained solid residue washed with ethyl acetate. The solid dried under vacuum at room temperature for 20-24 hrs to give 32.0 gm solid.
Yield: 93 %
HPLC Purity: 86%
Mass: m/z 717.3 (M-HC1- 1)
Example-3: Preparation of Strong anion exchange resin (Sulfate).
Indion GS-300 was treated with aqueous sulfate anion solution and then washed with DM water. It is directly used for sulfate salt.
Example-4: Synthesis of l-[[N-methyl-N-3-[(methylamino)acetoxymethyl]pyridin-2-yl] carbamoyloxy]ethyl-l-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl) thiazol-2-yl]butyl]-lH-[l ,2,4]-triazo-4-ium Sulfate
Dissolved 10.0 g l-[[N-methyl-N-3-[(methylamino)acetoxymethyl]pyridin-2-yl] carbamoyloxy]ethyl-l-[(2R,3R)-2-(2,5-difluorophenyl)-2-hydroxy-3-[4-(4-cyanophenyl) thiazol-2-yl]butyl]-lH-[l ,2,4]-triazo-4-ium iodide hydrochloride in 200 ml deminerahzed water and 30 ml methanol. The solution was cooled to about 0 to 5°C. The strong anion exchange resin (sulfate) was added to the cooled solution. The reaction mixture was stirred to about 60-80 minutes. The reaction was filtered and washed with 50ml of demineralized water and methylene chloride. The aqueous layer was lyophilized to obtain
(8.0 g) white solid.
Yield: 93 %
HPLC Purity: > 90%
Mass: m/z 717.4 (M- HS04) +
Claims
1. A solid amorphous form of isavuconazonium sulfate compound of Formula I
Formula I
characterized by at least one of the following properties;
i. a powder X-ray diffraction pattern substantially in accordance with Figure 1 ,
ii. a differential scanning calorimetric (DSC) thermogram substantially in accordance with Figure 2,
iii. a Thermogavimetric Analysis (TGA) substantially in accordance with Figure 3.
2. The isavuconazonium sulfate compound of claim 1, wherein the purity of isavuconazonium sulfate is more than 94 %, as measured HPLC.
3. A process for the preparing solid amorphous form of isavuconazonium sulfate compound of Formula I,
the process comprises of;
a) contacting isavuconazonium iodide hydrochloride compound of Formula IA
Formula IA
with anion exchange resin in the suitable solvent,
b) isolating isavuconazonium sulfate in the suitable solvent.
4. The process of claim 3, wherein the suitable solvent is selected from the group comprising one or more alcohol, amides, ether, acetates, hydrocarbon, water or mixture thereof.
5. The process of claim 3, wherein the anion exchange resin is selected from the group comprising one or more Diaion™ SA10A, Diaion™ SA1 1A, Diaion™ SA12A, Diaion™ NSA100, Diaion™ PA308, PA306, Amberjet 4000 CI, Amberjet 4400 CI and Amberjet 4600 CI.
6. A solid amorphous form of Isavuconazonium iodide hydrochloride compound of Formula IA
Formula IA
characterized by at least one of the following properties,
i. a powder X-ray diffraction pattern substantially in accordance with Figure 4;
ii. a differential scanning calorimetric (DSC) thermogram substantially in accordance with Figure 5,
iii. a Thermogavimetric Analysis (TGA) substantially in accordance with Figure 6.
7. The compound of claim 6, wherein the purity of isavuconazonium iodide hydrochloride is more than 90 %, as measured HPLC.
8. A solid amorphous form of Boc-Isavuconazonium iodide compound of formula (IV)
Formula IV
characterized by at least one of the following properties;
i. a powder X-ray diffraction pattern substantially in accordance with Figure 7 ;
ii. a differential scanning calorimetric (DSC) thermogram substantially in accordance with Figure 8,
iii. a Thermogavimetric Analysis (TGA) substantially in accordance with Figure 9.
9. The compound of claim 8, wherein the purity of Boc-isavuconazonium iodide, has the purity more than 90%, as measured HPLC.
10. A process for the preparation isavuconazonium iodide hydrochloride compound of Formula IA,
Formula IA
the process comprises of,
a) reacting isavuconazole compound of formula (II) or salt thereof
Formula II
with [N-methyl-N-3((tert-butoxycarbonylmethylamino)acetoxymethyl)pyridine- 2-yl] carbamic acid 1 -chloro-ethyl ester or salt thereof compound of formula (III)
Formula III
in presence of iodide salt, in the suitable solvent to obtain Boc -protected isavuconazonium iodide com ound of formula (IV)
Formula IV
b) deprotecting Boc -protected isavuconazonium iodide compound of formula (IV) with hydrochloric acid in suitable solvent to obtain isavuconazonium iodide hydrochloride compound of Formula IA.
11. The process of claim 10, wherein the suitable solvent used in step (a) is selected from the group comprising nitrile, ether, amides, alcohol, acetates, hydrocarbon, water or mixture thereof.
12. The process of claim 10, wherein the suitable solvent used in step (b) is selected from the group comprising acetates, alcohols, amides, ether, chlorinated solvents, water or mixture thereof.
13. The suitable solvent of claim 10, contains hydrochloric acid 12% to 20% w/v.
14. The process of claim 10, wherein the iodide salt is selected from the group comprising potassium iodide and sodium iodide.
15. The process according to claim 10, wherein isavuconazonium iodide hydrochloride compound of formula-IA subsequently converted to isavuconazonium or a pharmaceutically acceptable salt thereof.
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| CN110128420A (en) * | 2019-05-08 | 2019-08-16 | 阴启明 | Bisulfate ion/sulfate radical type anionexchangetechnique preparation Chinese mugwort Saperconazole monosulfate method |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6812238B1 (en) | 1999-11-02 | 2004-11-02 | Basilea Pharmaceutica Ag | N-substituted carbamoyloxyalkyl-azolium derivatives |
-
2015
- 2015-07-21 WO PCT/IB2015/055511 patent/WO2016016766A2/en active Application Filing
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6812238B1 (en) | 1999-11-02 | 2004-11-02 | Basilea Pharmaceutica Ag | N-substituted carbamoyloxyalkyl-azolium derivatives |
| US7189858B2 (en) | 1999-11-02 | 2007-03-13 | Basilea Pharmaceutica Ag | N-phenyl substituted carbamoyloxyalkyl-azolium derivatives |
| US7459561B2 (en) | 1999-11-02 | 2008-12-02 | Basilea Pharmaceutica Ag | N-substituted carbamoyloxyalkyl-azolium derivatives |
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| CN113024539B (en) * | 2019-12-25 | 2023-11-28 | 上海迪赛诺医药集团股份有限公司 | Preparation method of isaconazole onium sulfate |
| CN113024539A (en) * | 2019-12-25 | 2021-06-25 | 上海迪赛诺生物医药有限公司 | Preparation method of isavuconazole onium sulfate |
| WO2024037212A1 (en) * | 2022-08-17 | 2024-02-22 | 扬子江药业集团上海海尼药业有限公司 | Preparation method for isavuconazonium sulfate |
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| WO2016016766A3 (en) | 2016-03-24 |
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