WO2018067805A1 - Formes à l'état solide de sotagliflozine - Google Patents

Formes à l'état solide de sotagliflozine Download PDF

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Publication number
WO2018067805A1
WO2018067805A1 PCT/US2017/055321 US2017055321W WO2018067805A1 WO 2018067805 A1 WO2018067805 A1 WO 2018067805A1 US 2017055321 W US2017055321 W US 2017055321W WO 2018067805 A1 WO2018067805 A1 WO 2018067805A1
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WO
WIPO (PCT)
Prior art keywords
sotagliflozin
theta
solid state
state forms
crystalline form
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PCT/US2017/055321
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English (en)
Inventor
Stefano Luca Giaffreda
Enrico MODENA
Cristina IANNI
Anantha Rajmohan MUTHUSAMY
Sundara Lakshmi Kanniah
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Teva Pharmaceutical Industries Ltd.
Teva Pharmaceuticals Usa, Inc.
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Application filed by Teva Pharmaceutical Industries Ltd., Teva Pharmaceuticals Usa, Inc. filed Critical Teva Pharmaceutical Industries Ltd.
Publication of WO2018067805A1 publication Critical patent/WO2018067805A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics

Definitions

  • the present invention relates to solid state forms of Sotagliflozin, processes for preparation thereof and pharmaceutical compositions thereof.
  • Sotagliflozin has the chemical name (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4- ethoxybenzyl)phenyl)-6-(methylthio)tetrahydro-2H- pyran-3,4,5-triol. Sotagliflozin has the following chemical structure:
  • Sotagliflozin is an orally available L-xyloside based molecule that apparently inhibits both sodium-glucose transporter type 1 (SGLT1) and type 2 (SGLT2).
  • SGLT1 is primarily responsible for glucose and galactose absorption in the gastrointestinal tract, and SGLT2 is responsible for most of the glucose reabsorption performed by the kidney.
  • Sotagliflozin is known from WO 2008/109591. Amorphous forms and crystalline forms (i.e. Form 1 and Form 2) of Sotagliflozin are disclosed in WO2010/009197.
  • Polymorphism the occurrence of different crystal forms, is a property of some molecules and molecular complexes.
  • a single compound like Sotagliflozin, may give rise to a variety of polymorphs having distinct crystal structures and physical properties like melting point, thermal behaviors (e.g. measured by thermogravimetric analysis - "TGA”, or differential scanning calorimetry - “DSC”), powder X-ray diffraction (PXRD) pattern, infrared absorption fingerprint, Raman absorption fingerprint, and solid state (13C-) NMR spectrum.
  • TGA thermogravimetric analysis -
  • DSC differential scanning calorimetry -
  • PXRD powder X-ray diffraction
  • Different salts and solid state forms (including solvated forms) of an active pharmaceutical ingredient may possess different properties. Such variations in the properties of different salts and solid state forms and solvates may provide a basis for improving formulation, for example, by facilitating better processing or handling characteristics, improving the dissolution profile, or improving stability (polymorph as well as chemical stability) and shelf-life. These variations in the properties of different salts and solid state forms may also provide improvements to the final dosage form, for instance, if they serve to improve bioavailability. Different salts and solid state forms and solvates of an active pharmaceutical ingredient may also give rise to a variety of polymorphs or crystalline forms, which may in turn provide additional opportunities to use variations in the properties and characteristics of a solid active pharmaceutical ingredient for providing an improved product.
  • Discovering new salts, solid state forms and solvates of a pharmaceutical product can provide materials having desirable processing properties, such as ease of handling, ease of processing, storage stability, and ease of purification or as desirable intermediate crystal forms that facilitate conversion to other salts or polymorphic forms.
  • New salts, polymorphic forms and solvates of a pharmaceutically useful compound can also provide an opportunity to improve the performance characteristics of a pharmaceutical product (dissolution profile, bioavailability, etc.). It enlarges the repertoire of materials that a formulation scientist has available for formulation optimization, for example by providing a product with different properties, e.g., a different crystal habit, higher crystallinity or polymorphic stability which may offer better processing or handling characteristics, improved dissolution profile, or improved shelf-life. For at least these reasons, there is a need for additional salts and solid state forms (including solvated forms) of Sotagliflozin.
  • the present invention relates to solid state forms of Sotagliflozin, to processes for preparation thereof, and to pharmaceutical compositions comprising these solid state forms.
  • the present invention also provides the use of any one of the solid state forms of Sotagliflozin for preparing other solid state forms of Sotagliflozin or its salts, and solid state forms thereof.
  • the present invention encompasses any one of the above described solid state forms of Sotagliflozin and /or combinations thereof for use in the preparation of pharmaceutical compositions and/or formulations, preferably for the treatment of type 1 and/or 2 diabetes mellitus.
  • the present invention further provides pharmaceutical compositions comprising any one of or a mixture of the solid state forms of Sotagliflozin according to the present invention.
  • the present invention encompasses
  • compositions comprising any one of the above described solid state forms of Sotagliflozin and /or combinations thereof and at least one pharmaceutically acceptable excipient.
  • the present invention encompasses processes to prepare said pharmaceutical formulations of Sotagliflozin comprising combining any one of the above solid state forms and /or combinations thereof and at least one pharmaceutically acceptable excipient.
  • the present invention encompasses the use of any one of the above described solid state forms of Sotagliflozin and /or combinations thereof for the preparation of pharmaceutical compositions and/or formulations.
  • any of the solid state forms as defined herein and /or combinations thereof as well as the pharmaceutical compositions or formulations of the solid state forms of Sotagliflozin can be used as medicaments, particularly for the treatment of type 1 and/or 2 diabetes mellitus.
  • the present invention also provides a method of treating type 1 and/or 2 diabetes mellitus; comprising administering a therapeutically effective amount of any one of the solid state forms of Sotagliflozin of the present invention and /or combinations thereof, or at least one of the above pharmaceutical compositions or formulations, to a subject suffering from type 1 and/or 2 diabetes mellitus, or otherwise in need of the treatment.
  • Figure 1 shows a powder X-ray diffraction pattern ("powder XRD” or "PXRD”) of Sotagliflozin Form A.
  • Figure 3 shows a powder X-ray diffraction pattern of Sotagliflozin Form C.
  • Figure 4 shows a powder X-ray diffraction pattern of Sotagliflozin Form D.
  • Figure 9 shows a powder X-ray diffraction pattern of Sotagliflozin Form I.
  • Figure 10 shows a powder X-ray diffraction partem of Sotagliflozin Form K.
  • Figure 11 shows a powder X-ray diffraction partem of Sotagliflozin form-2 according to WO 2010009197.
  • the present invention relates to Sotagliflozin, to solid state forms thereof, such as crystalline Forms A, B, C, D, E, F, G, H, I and K; to processes for preparation thereof and to pharmaceutical compositions comprising at least one of, or a combination of, these solid state forms.
  • the invention also relates to the conversion of Sotagliflozin Forms A, B, C, D, E, F, G, H, I and/or K to other solid state forms of Sotagliflozin or to its salts and solid state forms thereof.
  • the solid state forms of Sotagliflozin of the present invention may have advantageous properties selected from at least one of: chemical or polymorphic purity, flowability, solubility, dissolution rate, bioavailability, morphology or crystal habit, stability - such as chemical stability as well as thermal and mechanical stability with respect to polymorphic conversion, stability towards dehydration and/or storage stability, a lower degree of hygroscopicity, low content of residual solvents and advantageous processing and handling characteristics such as compressibility, or bulk density.
  • a crystal form may be referred to herein as being characterized by graphical data "as depicted in" a Figure.
  • Such data include, for example, powder X-ray diffractograms and solid state NMR spectra.
  • the graphical data potentially provides additional technical information to further define the respective solid state form (a so-called "fingerprint") which can not necessarily be described by reference to numerical values or peak positions alone.
  • the skilled person will understand that such graphical representations of data may be subject to small variations, e.g., in peak relative intensities and peak positions due to factors such as variations in instrument response and variations in sample concentration and purity, which are well known to the skilled person.
  • a crystal form of Sotagliflozin e.g. Sotagliflozin Form A, referred to herein as being characterized by graphical data "as depicted in" a Figure will thus be understood to include any crystal forms of the Sotagliflozin, e.g., Sotagliflozin Form A, characterized with the graphical data having such small variations, as are well known to the skilled person, in comparison with the Figure.
  • a solid state form (or polymorph) may be referred to herein as
  • solid state of Sotagliflozin described herein as substantially free of any other solid state forms would be understood to contain greater than 80% (w/w), greater than 90% (w/w), greater than 95% (w/w), greater than 98% (w/w), or greater than 99% (w/w) of the subject solid state form of Sotagliflozin.
  • the described solid state forms of Sotagliflozin may contain from 1% to 20% (w/w), from 5% to 20% (w/w), or from 5% to 10% (w/w) of one or more other solid state forms of Sotagliflozin.
  • a process or step may be referred to herein as being carried out “overnight. " This refers to a time interval, e.g., for the process or step, that spans the time during the night, when that process or step may not be actively observed. This time interval is from about 8 to about 20 hours, or about 10-18 hours, typically about 16 hours.
  • dry crystalline form refers to a polymorph that was dried using any conventional techniques to remove residual solvent.
  • conventional techniques can be, but are not limited to, evaporation, vacuum drying, oven drying, drying under nitrogen flow, etc.
  • solvate refers to a crystal form that incorporates a solvent in the crystal structure.
  • the solvent is water, the solvate is often referred to as a "hydrate".
  • the solvent in a solvate may be present in either a stoichiometric or in a non-stoichiometric amount.
  • the amount of solvent employed in a chemical process may be referred to herein as a number of "volumes” or “vol” or “V.”
  • a material may be referred to as being suspended in 10 volumes (or 10 vol or 10V) of a solvent.
  • this expression would be understood to mean milliliters of the solvent per gram of the material being suspended, such that suspending 5 grams of a material in 10 volumes of a solvent means that the solvent is used in an amount of 10 milliliters of the solvent per gram of the material that is being suspended or, in this example, 50 mL of the solvent.
  • v/v may be used to indicate the number of volumes of a solvent that are added to a liquid mixture based on the volume of that mixture. For example, adding methyl tert-butyl ether (MTBE) (1.5 v/v) to a 100 ml reaction mixture would indicate that 150 mL of MTBE was added.
  • MTBE methyl tert-butyl ether
  • Sotagliflozin refers to less than 0.2% (w/w) absorption of water at 25°C and 75% relative humidity (RH), by the crystalline Sotagliflozin as determined for example by TGA.
  • non-hygroscopic in relation to crystalline Sotagliflozin refers to less than 0.2% (w/w) absorption of water at 25°C and 75% relative humidity (RH) after 24 hours, by the crystalline Sotagliflozin as determined for example by TGA and/or KF.
  • Water can be for example atmospheric water. It is understood that the term w/w (weight per weight) refers to weight percentage of a starting material prior to the test conditions. For example, by less than 0.2% (w/w) water it is meant that following storage at the test conditions, the weight gain of the starting material is less than 0.2%. As used herein, the term “reduced pressure” refers to a pressure of about 10 mbar to about 50 mbar.
  • thermo-dynamical stability in relation to solid state forms of Sotagliflozin refers to resistance of the solid state form to polymorphic conversion under certain conditions, for example, heating, melting or dissolving. In some embodiments, the term refers to less than 20%, 10%, 5%, 1 %, or 0.5% (w/w) conversion of crystalline Sotagliflozin to any other solid state form of Sotagliflozin as measured by PXRD. In some embodiments, the conversion is l%-20%, 1%-10% or l%-5% (w/w).
  • Sotagliflozin Form-2 as described in WO 2010009197 has an XRPD partem depicted in figure 11.
  • Form -2 of Sotagliflozin as described in WO 2010009197 contains peaks at one or more of about 4.4, 4.8, 14.5, 14.7, 15.5, 21.2, 22.1 and/or 23.8 degrees (deg) 2-theta.
  • the present invention comprises a crystalline form of Sotagliflozin designated as Form A.
  • the crystalline Form A of Sotagliflozin can be characterized by data selected from one or more of the following: a PXRD pattern having peaks at 3.7, 9.0, 9.6, 10.9, 12.7, 14.7 and 17.2 deg-2-theta ⁇ 0.1 deg 2-theta; a PXRD pattern as depicted in figure 1 ; and combinations of these data.
  • crystalline Form A of Sotagliflozin may be a hydrate, specifically a monohydrate.
  • Form A of Sotagliflozin may contain from about 3% to about 6% of water by weight, preferably about 3 to 4 % of water by weight as measured by Karl Fischer titration and/or TGA.
  • the present invention comprises a crystalline form of Sotagliflozin designated as Form B.
  • the crystalline Form B of Sotagliflozin can be characterized by data selected from one or more of the following: a PXRD pattern having peaks at 3.6, 13.3, 14.6, 18.1 and 22.8 deg-2-theta ⁇ 0.1 deg 2-theta; a PXRD pattern as depicted in Figure 2; and combinations of these data.
  • Crystalline Form B of Sotagliflozin may be further characterized by the PXRD pattern having peaks at 3.6, 13.3, 14.6, 18.1 and 22.8 deg-2-theta ⁇ 0.1 deg 2-theta, and also having one, two, three or four additional peaks selected from 4.4, 9.1 , 10.5 and 20.7 deg-2-theta ⁇ 0.1 deg 2-theta.
  • the present invention comprises a crystalline form of Sotagliflozin designated as Form C.
  • the crystalline Form C of Sotagliflozin can be characterized by data selected from one or more of the following: a PXRD pattern having peaks at 4.9, 7.3, 7.8, 9.6, 10.7, 11.1 , and 20.1 deg-2-theta ⁇ 0.1 deg 2-theta, a PXRD pattern as depicted in Figure 3; and combinations of these data.
  • Crystalline Form C of Sotagliflozin may be further characterized by the PXRD pattern having peaks at 4.9, 7.3, 7.8, 9.6, 10.7, 11.1, and 20.1 deg-2-theta ⁇ 0.1 deg 2- theta, and also having one, two, three or four additional peaks selected from 3.7, 13.4, 20.7, and 21.5 deg-2-theta ⁇ 0.1 deg 2-theta.
  • Crystalline Form D of Sotagliflozin may be further characterized by the PXRD pattern having peaks at 5.4, 6.5, 6.8, 9.9, 12.2 and 15.1 deg-2-theta ⁇ 0.1 deg 2-theta, and also having one, two, three or four additional peaks selected from 10.4, 13.6, 17.6 and 24.2 deg-2-theta ⁇ 0.1 deg 2-theta.
  • the present invention comprises a crystalline form of Sotagliflozin designated as Form E.
  • the crystalline Form E of Sotagliflozin can be characterized by data selected from one or more of the following: a PXRD pattern having peaks at 12.6, 12.9, 14.7, 15.0 and 19.7 deg-2-theta ⁇ 0.1 deg 2-theta, a PXRD pattern as depicted in Figure 5; and combinations of these data.
  • crystalline Form E of Sotagliflozin may be anhydrous. In an embodiment, crystalline Form E of Sotagliflozin is non-hygroscopic. Form E of Sotagliflozin may contain from about 0% to about 1 % of water by weight, preferably about less than 1 % of water by weight as measured by Karl Fischer titration and/or TGA.
  • the present invention comprises a crystalline form of Sotagliflozin designated as Form F.
  • the crystalline Form F of Sotagliflozin can be characterized by data selected from one or more of the following: a PXRD pattern having peaks at 6.4, 6.9, 12.2, 13.0, 14.0 and 20.3 deg-2-theta ⁇ 0.1 deg 2-theta, a PXRD pattern as depicted in Figure 6; and combinations of these data.
  • Crystalline Form F of Sotagliflozin may be further characterized by the PXRD pattern having peaks at 6.4, 6.9, 12.2, 13.0,14.0 and 20.3 deg-2-theta ⁇ 0.1 deg 2- theta, and also having one or two additional peaks selected from 3.4 and 22.2 deg-2-theta ⁇ 0.1 deg 2-theta.
  • Crystalline Form G of Sotagliflozin may be further characterized by the PXRD pattern having peaks at 5.6, 8.8, 13.0, 13.7, 18.4 and 22.5 deg-2-theta ⁇ 0.1 deg 2- theta, and also having one, two or three additional peaks selected from 8.1, 12.1 and 17.7 deg-2-theta ⁇ 0.1 deg 2-theta.
  • Crystalline Form H of Sotagliflozin may be further characterized by the PXRD pattern having peaks at 13.3, 16.0, 17.5, 21.0, 21.9 and 28.7 deg-2-theta ⁇ 0.2 deg 2- theta, and also having one, two or three additional peaks selected from 9.7, 19.7 and 27.7 deg-2-theta ⁇ 0.2 deg 2-theta.
  • the present invention comprises a crystalline form of Sotagliflozin designated as Form K.
  • the crystalline Form K of Sotagliflozin can be characterized by data selected from one or more of the following: a PXRD pattern having peaks at 6.2, 6.4, 10.9, 17.8, 18.7, 19.3 and 20.0 deg-2-theta ⁇ 0.1 deg 2-theta, a PXRD pattern as depicted in Figure 10; and combinations of these data.
  • Crystalline Form K of Sotagliflozin may be further characterized by the PXRD pattern having peaks at 6.2, 6.4, 10.9, 17.8, 18.7, 19.3 and 20.0 deg-2-theta ⁇ 0.1 deg 2-theta and also having one, two or three additional peaks selected from 3.7, 10.5 and 15.7 deg-2-theta ⁇ 0.1 deg 2-theta.
  • the solid forms of the present disclosure may exhibit favorable specific surface area properties.
  • the present invention also provides the use of any one of the solid state forms of Sotagliflozin for preparing other solid state forms of Sotagliflozin or Sotagliflozin salts, and solid state forms thereof.
  • the present invention encompasses any one of the above described solid state forms of Sotagliflozin and/ or combinations thereof for use in the preparation of pharmaceutical compositions, preferably for the treatment of type 1 and/or 2 diabetes mellitus.
  • the present invention comprises a process for preparing the above mentioned pharmaceutical compositions.
  • the present invention encompasses a process to prepare said formulations of Sotagliflozin comprising combining any one of the above solid state forms and/or combinations thereof and at least one pharmaceutically acceptable excipient. [0074] In another embodiment the present invention encompasses the use of any one of the above described solid state forms of Sotagliflozin and/or combinations thereof for the preparation of pharmaceutical compositions and/or formulations.
  • any one of the solid state forms as defined herein and/or combinations thereof, as well as the pharmaceutical compositions or formulations of Sotagliflozin can be used as medicaments, particularly for the treatment of type 1 and/or 2 diabetes mellitus.
  • Powder X-ray diffraction pattern (“PXRD”) method:
  • Sotagliflozin Form-2 may be prepared according to WO2010/009197. Sotaglifiozin Form-2 may also be prepared according to Example 16 below.
  • Sotagliflozin (Amorphous form, prepared according to example 1) was suspended in 2 ml of Toluene at room temperature (20-25 °C). The suspension was stirred for 15days which was filtered under vacuum and was dried at room temperature by vacuum suction. Sotagliflozin Form B has been confirmed by PXRD as presented in figure 2.
  • Sotagliflozin (Amorphous form, prepared according to example 1) was suspended in 2 ml of Heptane at room temperature (20-25 °C). The suspension was stirred for 15days which was filtered under vacuum and was dried at room temperature by vacuum suction. Sotagliflozin Form B has been confirmed by PXRD.
  • Sotagliflozin (Amorphous form, prepared according to example 1) was suspended in 2 ml of Mesitylene at room temperature (20-25°C). The suspension was stirred for 15days which was filtered under vacuum and was dried at room temperature by vacuum suction. Sotagliflozin Form B has been confirmed by PXRD.
  • Sotagliflozin (Amorphous form, prepared according to example 1) was suspended in 2 ml of Water at 50°C. The suspension was stirred for 72hrs which was filtered under vacuum and was dried at room temperature by vacuum suction. Sotagliflozin Form C has been confirmed by PXRD as presented in figure 3.
  • Sotagliflozin Form G has been confirmed by PXRD as presented in figure 7.

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Abstract

L'invention concerne des formes à l'état solide du Sotagliflozine, leurs procédés de préparation et leurs compositions pharmaceutiques.
PCT/US2017/055321 2016-10-06 2017-10-05 Formes à l'état solide de sotagliflozine WO2018067805A1 (fr)

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US201662405086P 2016-10-06 2016-10-06
US62/405,086 2016-10-06
IN201611039767 2016-11-22
IN201611039767 2016-11-22

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3771480A1 (fr) * 2019-08-01 2021-02-03 Lexicon Pharmaceuticals, Inc. Procédé continu de préparation de la forme cristalline ii de sotagliflozine
EP3771718A1 (fr) * 2019-08-01 2021-02-03 Lexicon Pharmaceuticals, Inc. Procédé de préparation de la forme cristalline ii de sotagliflozine

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008109591A1 (fr) 2007-03-08 2008-09-12 Lexicon Pharmaceuticals, Inc. Analogues de phlorizine utilisés comme inhibiteurs du co-transporteur 2 du sodium-glucose
WO2010009197A1 (fr) 2008-07-17 2010-01-21 Lexicon Pharmaceuticals, Inc. Formes solides de (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-éthoxybenzyl)phényl)-6-(méthylthio)tétrahydro-2h-pyran-3,4,5-triol et procédés de leur utilisation

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2008109591A1 (fr) 2007-03-08 2008-09-12 Lexicon Pharmaceuticals, Inc. Analogues de phlorizine utilisés comme inhibiteurs du co-transporteur 2 du sodium-glucose
WO2010009197A1 (fr) 2008-07-17 2010-01-21 Lexicon Pharmaceuticals, Inc. Formes solides de (2s,3r,4r,5s,6r)-2-(4-chloro-3-(4-éthoxybenzyl)phényl)-6-(méthylthio)tétrahydro-2h-pyran-3,4,5-triol et procédés de leur utilisation

Non-Patent Citations (1)

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Title
CAIRA ED - MONTCHAMP JEAN-LUC: "Crystalline Polymorphism of Organic Compounds", TOPICS IN CURRENT CHEMISTRY; [TOPICS IN CURRENT CHEMISTRY], SPRINGER, BERLIN, DE, vol. 198, 1 January 1998 (1998-01-01), pages 163 - 208, XP008166276, ISSN: 0340-1022 *

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3771480A1 (fr) * 2019-08-01 2021-02-03 Lexicon Pharmaceuticals, Inc. Procédé continu de préparation de la forme cristalline ii de sotagliflozine
EP3771718A1 (fr) * 2019-08-01 2021-02-03 Lexicon Pharmaceuticals, Inc. Procédé de préparation de la forme cristalline ii de sotagliflozine
WO2021019509A1 (fr) * 2019-08-01 2021-02-04 Lexicon Pharmaceuticals,Inc. Procédé continu pour la préparation d'une forme cristalline ii de sotagliflozine
WO2021019507A1 (fr) * 2019-08-01 2021-02-04 Lexicon Pharmaceuticals, Inc. Procédé de préparation de la forme cristalline ii de la sotagliflozine
CN114258397A (zh) * 2019-08-01 2022-03-29 莱西肯医药有限公司 制备结晶ii型索格列净的方法
CN114269728A (zh) * 2019-08-01 2022-04-01 莱西肯医药有限公司 制备结晶ii型索格列净的连续方法

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