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WO2024027013A1 - Forme cristalline ii d'elobixibat et son procédé de préparation - Google Patents

Forme cristalline ii d'elobixibat et son procédé de préparation Download PDF

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Publication number
WO2024027013A1
WO2024027013A1 PCT/CN2022/124083 CN2022124083W WO2024027013A1 WO 2024027013 A1 WO2024027013 A1 WO 2024027013A1 CN 2022124083 W CN2022124083 W CN 2022124083W WO 2024027013 A1 WO2024027013 A1 WO 2024027013A1
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WO
WIPO (PCT)
Prior art keywords
crystal form
eloxibate
ketones
eloxibat
ray powder
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/CN2022/124083
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English (en)
Chinese (zh)
Inventor
曹铭
陈玉凤
陈道玉
邹洁
张姿微
金飞敏
杨绍波
郑保富
高强
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Shanghai Haoyuan Chemexpress Co Ltd
Original Assignee
Shanghai Haoyuan Chemexpress Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Shanghai Haoyuan Chemexpress Co Ltd filed Critical Shanghai Haoyuan Chemexpress Co Ltd
Priority to KR1020257006700A priority Critical patent/KR20250040737A/ko
Priority to JP2025505764A priority patent/JP2025525154A/ja
Priority to CN202280060973.7A priority patent/CN117980295A/zh
Publication of WO2024027013A1 publication Critical patent/WO2024027013A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D281/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D281/02—Seven-membered rings
    • C07D281/04—Seven-membered rings having the hetero atoms in positions 1 and 4
    • C07D281/08—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
    • C07D281/10—Seven-membered rings having the hetero atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A61K31/554—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one sulfur as ring hetero atoms, e.g. clothiapine, diltiazem
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/10—Laxatives
    • 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
    • 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
    • A61P3/06—Antihyperlipidemics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Definitions

  • the present invention relates to the crystal form of eloxibate and belongs to the technical fields of medicine and chemistry.
  • Elobixibat is a drug developed by Albireo AB (trade name: Goofice). It is the world's first approved bile acid transport inhibitor drug. It was approved by PMDA in January 2018 for the treatment of chronic constipation. Compared with traditional intestinal secretagogues and intestinal prokinetic drugs, eloxibate can effectively reduce the hardness of defecation and increase the frequency of defecation, improve the smoothness of defecation and cause less abdominal cramps or pain. The structural formula of this compound is shown below:
  • Patent WO2002050051A1 discloses compounds of formula (1) and preparation methods and pharmaceutical compositions thereof.
  • Patent WO2014174066A1 discloses a crystalline monohydrate IV of eloxibate. Its X-ray powder diffraction pattern has characteristic peaks at 2 ⁇ values of 6.3 ⁇ 0.2°, 19.4 ⁇ 0.2°, 10.2 ⁇ 0.2°, 10.5 ⁇ 0.2°, and 9.4 ⁇ 0.2° and 9.5 ⁇ 0.2°; crystal modifications EtOH-1, crystal modification MeOH-1, crystal modification 1-PrOH-1 and crystal modification 2-PrOH-1 of eloxibate are also disclosed.
  • Patent CN112375044A (WO2016062848A1) discloses anhydrous form C, dihydrate crystal form E, anhydrous form F, anhydrous form L and dihydrate crystal form N; among which anhydrous form C and anhydrous form L are highly hygroscopic, It will turn into crystalline hydrate at 30-70% RH. The water and environmental humidity must be strictly controlled during actual production or preparation process.
  • the CN112375044A patent also discloses that the preparation method of the anhydrous form F needs to be prepared through the solid-solid transformation of the solvate. Specifically, the solvate MIBK solvate G or EA solvate H is first prepared, and then the solvate is prepared at a high temperature of 100°C.
  • eloxibate compounds are easy to form solvates. Due to the problem of residual dissolution, these solvates have poor pharmaceutical properties; eloxibate hydrates and anhydrous products often have hygroscopic properties or preparation conditions. Harsh; only the crystalline form F has acceptable hygroscopicity and relatively good stability, but its preparation process is obtained by drying the corresponding MIBK solvate G and EA solvate H at 100°C at high temperature. This method is not conducive to Industrial production and quality control.
  • the invention provides a new crystal form of eloxibate and a preparation method thereof.
  • the crystal form has stable physical and chemical properties and can meet the requirements of low hygroscopicity for medicinal purposes.
  • the preparation method of the crystal form is easy to operate and is conducive to industrial production.
  • the present invention provides an anhydrous crystal form II of eloxibat with good stability (hereinafter also referred to as "crystalline form II") and a preparation method thereof.
  • the present invention provides a crystal form II of eloxibate, the X-ray powder diffraction pattern of which has characteristic peaks at 2 ⁇ values of 9.4 ⁇ 0.2° and 7.8 ⁇ 0.2°.
  • the invention provides a crystal form II of eloxibate, the X-ray powder diffraction pattern of which has characteristic peaks at 2 ⁇ values of 9.4 ⁇ 0.2° and 7.8 ⁇ 0.2° and has one or more of the following characteristic peaks: 3.9 ⁇ 0.2 °, 11.7 ⁇ 0.2°, 16.1 ⁇ 0.2°, 17.6 ⁇ 0.2°, 18.3 ⁇ 0.2°, 19.6 ⁇ 0.2°, 20.9 ⁇ 0.2°, 22.1 ⁇ 0.2° and 25.8 ⁇ 0.2°.
  • the X-ray powder diffraction pattern of the crystal form II of eloxibate of the present invention also has characteristic peaks at 2 ⁇ values of 3.9 ⁇ 0.2°, 8.8 ⁇ 0.2°, and 19.6 ⁇ 0.2°.
  • the invention provides a crystal form II of eloxibate, the X-ray powder diffraction pattern of which has 2 ⁇ values of 3.9 ⁇ 0.2°, 7.8 ⁇ 0.2°, 9.4 ⁇ 0.2°, 11.7 ⁇ 0.2°, 16.1 ⁇ 0.2°, 17.6
  • the XRPD pattern of crystal form II of the compound of formula I of the present invention is consistent with Figure 1 or Figure 2.
  • the present invention relates to a method for preparing crystalline Form II, comprising the following method:
  • the raw material eloxibat in the method one or two is amorphous eloxibat or another crystal form of eloxibat.
  • the raw material eloxibat is the eloxibat monohydrate crystal form IV reported in WO2014174066A1.
  • other raw materials of eloxibat may also be used, such as other solvates of eloxibat (for example, those reported in WO2014174066A1 or CN112375044A (WO2016062848A1) or crystal forms prepared by other conventional crystallization methods), or may also be used It is amorphous.
  • the mass volume ratio (g: mL) of the mixed solvent of eloxibat and ketones or ketones and liquid alkanes is 1:5 to 100, preferably 1 :15 ⁇ 30.
  • the ketone in method one or two is preferably acetone;
  • the liquid alkane is preferably at least one of pentane, n-hexane or n-heptane, and further preferably n-hexane or n-heptane. At least one.
  • the volume ratio of ketones to liquid alkanes in method one or method two is preferably 2:1 to 1:15; preferably the ketone is acetone and the liquid alkane is n-hexane or n-heptane; The volume ratio of acetone to n-hexane or n-heptane is 2:1 to 1:15, preferably 1:3 to 1:10.
  • drying in the first or second method is preferably carried out under vacuum or normal pressure blast drying at 30-60°C; the preferred drying time is 1-24 hours.
  • step a) of method 1 is to dissolve the raw material eloxibat in ketones or a mixed solvent of ketones and liquid alkanes, and the solution can be heated to dissolve it.
  • the temperature is preferably raised to 50-60°C; the rate of heating and cooling does not have a decisive influence on the formation of crystal form II.
  • it is recommended to heat at a rate of 5 to 30°C/min; specifically, for example, to heat at a rate of 5 to 15°C/min.
  • step b) of method 1 it is recommended to cool down at a rate of 1 to 15°C/min, preferably naturally, to cool to room temperature.
  • the DSC pattern of crystalline Form II of eloxibate of the present invention includes an endothermic peak at 169.5 ⁇ 0.5°C.
  • the eloxibat crystal form II provided above by the present invention is heated from room temperature to 300°C using a thermogravimetric analyzer (TGA) at a heating rate of 10°C/min.
  • TGA thermogravimetric analyzer
  • the temperature is 150°C, there will be no more than 2% weight loss, and more preferably, no more than 1.2% weight loss.
  • Crystalline Form II is the acrystalline form. There is no risk of crystallization due to loss of solvent under reduced pressure and elevated temperature in the non-crystalline form. So only the solvent needs to be removed from the surface.
  • the solid is dried under vacuum at room temperature.
  • the crystal form II of eloxibate provided by the present invention is physically stable at room temperature.
  • the crystal form II does not absorb water molecules to form hydrate crystal form IV or any other hydrate crystal form.
  • the eloxibat crystal form II provided by the present invention is chemically pure and stable at room temperature, and the anhydrate crystal form II is exposed to 40°C/75% RH. Or in a 25°C/92.5%RH environment, the chemical purity of crystalline Form II has no significant change.
  • the eloxibat crystal form II provided by the present invention is slightly hygroscopic at 25°C and 0-90% RH environment, and XRPD shows no crystallization phenomenon.
  • the DVS isotherm of the crystal form II provided by the present invention has no obvious change in moisture (the moisture absorption of 1.1% in Figure 8 is significantly lower than the 5.0%, 0-90% RH of the crystal form C reported in CN112375044A (WO2016062848A1)), and the hygroscopicity
  • the XRPD spectra of the samples after testing are consistent, that is, there is no risk of crystallization during the adsorption and desorption process.
  • the crystal form II of the present invention is more conducive to industrial production; through comparison in Figure 10, there are obvious differences between the crystal form II of the present invention and all reported crystal forms in CN112375044A, and can be identified as different crystal forms.
  • the present invention also provides a medicine for treating constipation, which contains an active ingredient, and the active ingredient includes the crystal form II of the eloxibat crystal as described above; the medicine includes excipients other than the active ingredient, the selection of excipients, and the Preparation, etc. are common choices.
  • pharmaceutical excipients can be selected from: microcrystalline cellulose, D-mannitol, hypromellose, croscarmellose sodium, light anhydrous silicic acid, magnesium stearate , polyethylene glycol 6000, titanium oxide, yellow ferric oxide or carnauba wax, etc.
  • the active ingredient of the medicament of the present invention may only comprise the crystalline form II of eloxibat, and in this case, the crystalline form II of eloxibat is present in an effective amount.
  • the present invention has significantly improved solubility due to crystal form II, more flexible selection of excipients, and higher drug safety.
  • the new anhydrous crystal form of eloxibat crystal form II provided by the present invention not only has good stability, low hygroscopicity, meets pharmaceutical requirements, but also has significantly improved solubility. It is expected that it will have better Ideal drug selection and better bioavailability, as well as helping to increase potency and reduce dosage.
  • Crystal form II of the present invention can be dried under vacuum at 30-60°C without the risk of crystallization due to water loss.
  • Figure 1 is an X-ray powder diffraction (XPRD) pattern of crystal form II obtained in Example 1.1 of the present invention
  • Figure 2 is an X-ray powder diffraction (XPRD) pattern of crystal form II obtained in Example 1.2 of the present invention
  • FIG. 3 is a thermogravimetric analysis (TGA) spectrum of crystal form II obtained in Example 1.1 of the present invention
  • Figure 4 is a differential scanning calorimetry (DSC) spectrum of crystal form II obtained in Example 1.1 of the present invention.
  • Figure 5 is an X-ray powder diffraction comparison chart showing the stability of crystal form II obtained in Example 1.1 of the present invention before and after placement;
  • Figure 6 is an X-ray powder diffraction comparison chart showing the stability of crystal form C obtained in the comparative example of the present invention before and after placement;
  • Figure 7 is an X-ray powder diffraction comparison chart showing the stability of crystal form IV prepared according to the method of WO2014174066A1 before and after placement;
  • Figure 8 is a hygroscopicity test (DVS) chart of crystal form II obtained in Example 1.1 of the present invention.
  • Figure 9 is an X-ray powder diffraction comparison chart before and after the hygroscopicity test of the crystal form II obtained in Example 1.1 of the present invention.
  • Figure 10 is a comparison chart of X-ray powder diffraction of the crystal form II obtained in Example 1.1 of the present invention and the crystal form reported in the prior art.
  • the XPRD spectrum was collected on a Bruker D8 ADVANCE diffractometer.
  • the parameters of the X-ray powder diffraction method are as follows:
  • Tube voltage 40 kilovolts (kV)
  • Tube current 40 milliamps (mA)
  • Slits 2# scattering slit: 1°, 3# anti-scattering slit: 1°, 4# receiving slit: 0.3mm.
  • test tube The contents of the test tube were filtered and poured into a crystallization bowl, which was then vacuum dried at 60°C for 2 hours.
  • the sample was analyzed by XRPD, which showed that the solid form was Form C anhydrate.
  • the XRPD spectrum was compared with the anhydrous Form C disclosed in patent CN112375044A (WO2016062848A1) and was the same crystal form.
  • the X-ray powder diffraction pattern of the obtained solid product is shown in Figure 1.
  • the X-ray powder diffraction pattern of the obtained crystal form II has 2 ⁇ values of 3.9 ⁇ 0.2°, 7.8 ⁇ 0.2°, 9.4 ⁇ 0.2°, and 11.7 ⁇ 0.2 °, 16.1 ⁇ 0.2°, 17.6 ⁇ 0.2°, 18.3 ⁇ 0.2°, 19.6 ⁇ 0.2°, 20.9 ⁇ 0.2°, 22.1 ⁇ 0.2°, 25.8 ⁇ 0.2° and below: 8.5 ⁇ 0.2°, 8.8 ⁇ 0.2°, 10.4 ⁇ 0.2°, 11.1 ⁇ 0.2°, 13.0 ⁇ 0.2°, 14.0 ⁇ 0.2°, 14.5 ⁇ 0.2°, 15.1 ⁇ 0.2°, 17.1 ⁇ 0.2°, 19.0 ⁇ 0.2°, 20.6 ⁇ 0.2°, 21.3 ⁇ 0.2°, 22.6 ⁇ 0.2°, 23.7 ⁇ 0.2°, 24.5 ⁇ 0.2°, 24.7 ⁇ 0.2°, 26.6 ⁇ 0.2°, 27.2 ⁇ 0.2°, 27.5 ⁇ 0.2°, 28.4 ⁇ 0.2°, 28.6 ⁇ 0.2°, 29.9 ⁇ 0.2°, There are characteristic
  • the TGA spectrum of the obtained crystal form II is shown in Figure 3.
  • the TGA data shows that the crystal form has a weight loss of approximately 1.02% in the heating range of 0 to 150°C.
  • the DSC image of the obtained crystal form II is shown in Figure 4.
  • the crystal form II has a single melting endotherm peak at 164-200°C. Specifically, Form II has a single absorption peak at 169.5 ⁇ 0.5°C.
  • the X-ray powder diffraction pattern measured using Cu-K ⁇ rays of the prepared crystals is the same as that of Example 1.1.
  • the X-ray powder diffraction pattern measured using Cu-K ⁇ rays of the prepared crystals is the same as that of Example 1.1.
  • the X-ray powder diffraction pattern measured using Cu-K ⁇ rays of the prepared crystals is the same as that of Example 1.1.
  • the X-ray powder diffraction pattern measured using Cu-K ⁇ rays of the prepared crystals is the same as that of Example 1.1.
  • the X-ray powder diffraction pattern measured using Cu-K ⁇ rays of the prepared crystals is the same as that of Example 1.1.
  • the X-ray powder diffraction pattern measured using Cu-K ⁇ rays of the prepared crystals is the same as that of Example 1.1.
  • the X-ray powder diffraction pattern measured using Cu-K ⁇ rays of the prepared crystals is the same as that of Example 1.1.
  • the target crystal form II of the compound obtained in Example 1.1, the crystal form IV prepared according to the method of WO2014174066A, and the crystal form C obtained in the comparative example were placed under different temperatures and different humidity environments for 3 days or one week, and samples were taken for XRPD comparison. Crystal form, chemical purity measured by HPLC, as shown in Table 1 below:
  • the crystal form II obtained by the present invention and the crystal form IV prepared according to the method of WO2014174066A1 were stored in five different humidity and temperature conditions shown in Table 1 (25°C/60%RH, 40°C /75%RH, 25°C/92.5%RH, room temperature environment (28°C/66%RH) or 25°C/10%RH) for one week, there is no obvious change in the X-ray powder diffraction pattern, indicating that the crystalline form is in the above environment. Can be kept for at least a week.
  • the crystalline Form C exhibits a high degree of stability under five different humidity and temperature conditions shown in Table 1 (25°C/60%RH, 40°C/75%RH, 25°C/92.5%RH, room temperature environment (28°C/ The crystal form has changed after being stored under 66% RH) for three days, and crystallized into the crystal form E published in CN112375044A.
  • Crystalline form II and crystalline form IV still have good stability under high temperature and high humidity conditions.
  • crystalline form II of eloxibate shows excellent stability under both 40°C/75%RH and 25°C/92.5%RH conditions.
  • stability is the stability, with no change in the purity of crystalline Form II of eloxibate.
  • Patent CN112375044A discloses DVS without crystalline form C and crystalline form E. Crystalline form C will transform into crystalline hydrate E at 30-70% RH and absorb about 5% water at 90% humidity. In the actual production or preparation process Water and environmental humidity must be strictly controlled.
  • Patent WO2014174066A1 discloses the DVS of monohydrate crystal form IV. Crystal form IV absorbs about 2.45% water between 0% RH and 10% RH, and absorbs more than 3% water at 90% humidity. In the actual production or preparation process, the Moisture and environmental humidity must be controlled to prevent crystallization.
  • the crystal form II of the present application has good low hygroscopicity compared to the anhydrous form C disclosed in patent CN112375044A (WO2016062848A1) and the monohydrate crystal form IV disclosed in WO2014174066A1.
  • strict humidity control is not required to remain stable. It has low requirements on drug preparation process and storage conditions.
  • the invention provides a crystal form II of eloxibate and a preparation method thereof.
  • the crystal form has stable physical and chemical properties and can meet the requirements of low hygroscopicity for medicinal purposes.
  • the preparation method is easy to operate and can realize industrial production.

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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
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  • Obesity (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

L'invention concerne une forme cristalline II d'elobixibat. Le motif de diffraction de rayons X sur poudre de la forme cristalline II a des pics spécifiques à des valeurs 2θ de 9,4 ± 0,2° et 7,8 ± 0,2° et a un ou plusieurs des pics caractéristiques suivants : 3,9 ± 0,2°, 11,7 ± 0,2°, 16,1 ± 0,2°, 17,6 ± 0,2°, 18,3 ± 0,2°, 19,6 ± 0,2°, 20,9 ± 0,2°, 22,1 ± 0,2° et 25,8 ± 0,2°. La forme cristalline II est stable et présente une faible hygroscopicité ; lorsqu'elle est exposée à un environnement à humidité élevée de 25 °C/92,5 % RH, la pureté chimique de la forme cristalline II ne change pas de manière significative, et le motif de diffraction des rayons X sur poudre de la forme cristalline ne change pas de même ; de plus, la forme cristalline II implique un procédé de préparation simple et pratique, a de faibles exigences par rapport au procédé de préparation et aux conditions de stockage, et a une valeur médicinale élevée.
PCT/CN2022/124083 2022-08-02 2022-10-09 Forme cristalline ii d'elobixibat et son procédé de préparation Ceased WO2024027013A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
KR1020257006700A KR20250040737A (ko) 2022-08-02 2022-10-09 엘로빅시바트의 결정형 ii 및 이의 제조 방법
JP2025505764A JP2025525154A (ja) 2022-08-02 2022-10-09 エロビキシバットの結晶形態ｉｉ及びその調製方法
CN202280060973.7A CN117980295A (zh) 2022-08-02 2022-10-09 一种依洛西巴特晶型ii及其制备方法

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CN202210920202 2022-08-02
CN202210920202.2 2022-08-02

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1481373A (zh) * 2000-12-21 2004-03-10 1,5-苯并硫氮杂�化合物及其作为降血脂药的应用
CN105143194A (zh) * 2013-04-26 2015-12-09 依洛比克斯公司 依洛昔巴特的结晶修饰物
CN107001301A (zh) * 2014-10-24 2017-08-01 埃洛比克斯股份公司 依洛昔巴特的晶体形式
CN111836804A (zh) * 2018-03-09 2020-10-27 埃洛比克斯股份公司 用于制备依洛昔巴特的方法
EP4029860A1 (fr) * 2019-09-09 2022-07-20 Elobix Ab Procédé de production d'un composé 1,5-benzothiazépin

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1481373A (zh) * 2000-12-21 2004-03-10 1,5-苯并硫氮杂�化合物及其作为降血脂药的应用
CN105143194A (zh) * 2013-04-26 2015-12-09 依洛比克斯公司 依洛昔巴特的结晶修饰物
CN107001301A (zh) * 2014-10-24 2017-08-01 埃洛比克斯股份公司 依洛昔巴特的晶体形式
CN111836804A (zh) * 2018-03-09 2020-10-27 埃洛比克斯股份公司 用于制备依洛昔巴特的方法
EP4029860A1 (fr) * 2019-09-09 2022-07-20 Elobix Ab Procédé de production d'un composé 1,5-benzothiazépin

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KR20250040737A (ko) 2025-03-24
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