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WO2022206879A1 - Formes cristallines de composés sulfamoyle pyrrole amide et leurs procédés de préparation - Google Patents

Formes cristallines de composés sulfamoyle pyrrole amide et leurs procédés de préparation Download PDF

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Publication number
WO2022206879A1
WO2022206879A1 PCT/CN2022/084300 CN2022084300W WO2022206879A1 WO 2022206879 A1 WO2022206879 A1 WO 2022206879A1 CN 2022084300 W CN2022084300 W CN 2022084300W WO 2022206879 A1 WO2022206879 A1 WO 2022206879A1
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Prior art keywords
crystal form
formula
compound
crystal
present
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Chinese (zh)
Inventor
鲁霞
陈智雄
张晓宇
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Crystal Pharmatech Co Ltd
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Crystal Pharmatech Co Ltd
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    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
    • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/36—Oxygen or sulfur atoms

Definitions

  • the invention relates to the field of chemical medicine, in particular to a crystal form of a sulfamoyl pyrrole amide compound and a preparation method thereof.
  • Hepatitis B is caused by hepatitis B virus (HBV) infection.
  • HBV hepatitis B virus
  • the treatment of hepatitis B virus infection is mainly "functional treatment", which requires long-term or life-long medication to achieve “functional cure”, that is, the content of hepatitis B surface antigen (HBsAg) and HBV-DNA in serum is always maintained to an undetectable state, thereby improving residual liver damage or fibrosis and reducing the risk of hepatitis.
  • functional treatment which requires long-term or life-long medication to achieve “functional cure”
  • HBV is composed of two parts, the outer shell and the core part.
  • the core part includes the viral capsid composed of the core protein, the DNA polymerase and the viral pregenome (pgRNA) contained in it.
  • pgRNA viral pregenome
  • Hepatitis B virus capsid protein assembly regulator (CAM) can combine with core protein to interfere with the encapsidation process of pgRNA, thereby inhibiting the production of HBV in vivo.
  • CAMs are under clinical research. The CAM currently studied can be divided into two types: CAM-A and CAM-N.
  • CAM-A affects the structure of the core protein and prevents HBV from forming a capsid of normal structure and size;
  • CAM-N inhibits the inclusion process of viral DNA and pgRNA, thereby producing an empty capsid. Both CAMs can prevent normal viruses Formation of the capsid.
  • Pyrrole-2-carboxamide is a new type of CAM-N, the compound is currently in phase 2 clinical research for the treatment of hepatitis B, and its structural formula is as follows:
  • Patent WO2014/184350A1 discloses the compound of formula (I) and its synthesis process. Through column chromatography and multiple washing and purification processes, a small amount of the target product that meets the requirements is finally obtained. The preparation method is cumbersome and unfavorable for industrialized large-scale production. The patent does not mention relevant reports on the solid or crystalline form of the compound of formula (I).
  • crystallization process As the main method of chemical product purification, crystallization process has the advantages of simple operation, easy amplification, low cost, etc., and is a purification method widely used in chemical and pharmaceutical fields. In view of the complex preparation and purification process of the compound of formula (I) at present, and the difficulty of process amplification, it is necessary to find different crystalline forms of the compound of formula (I) to simplify the purification process of the final product in production and improve the purification efficiency.
  • the present invention provides two crystal forms A and B of the compound of formula (I) and their preparation methods and uses.
  • a pharmaceutical composition comprising the crystal of any one of 1 and 3 above and a pharmaceutically acceptable carrier.
  • a pharmaceutical composition having CAM activity comprising the crystal of any one of 1 and 3 above as an active ingredient.
  • a preventive or therapeutic agent for hepatitis B virus infection comprising the crystal according to any one of 1 and 3 above as an active ingredient.
  • the crystalline forms A and B of the compounds of the formula (I) provided by the present invention are in solubility, melting point, stability, dissolution, hygroscopicity, adhesion, fluidity, bioavailability, processability, purification.
  • advantages in at least one aspect of action, preparation production, safety, etc. which provide a new and better choice for the preparation of pharmaceutical preparations containing the compound of formula (I), and are of great significance to drug development.
  • the compound represented by formula (I) N-(3-cyano-4-fluoro-phenyl)-1-methyl-4- ⁇ [(1S)-2,2,2-trifluoro-1-methyl-
  • the A-type crystal of ethyl]sulfamoyl ⁇ pyrrole-2-carboxamide, namely crystal form A is characterized in that, using Cu-K ⁇ radiation, the X-ray powder diffraction of the crystal form A has a 2 ⁇ value of 6.8° ⁇ There are characteristic peaks at 0.2°, 13.6° ⁇ 0.2° and 22.1° ⁇ 0.2°,
  • the X-ray powder diffraction of the crystal form A has one or two or three 2 ⁇ values of 11.7° ⁇ 0.2°, 17.1° ⁇ 0.2°, 20.5° ⁇ 0.2° There are characteristic peaks.
  • the X-ray powder diffraction of the crystal form A has characteristic peaks at 2 ⁇ values of 11.7° ⁇ 0.2°, 17.1° ⁇ 0.2°, and 20.5° ⁇ 0.2°.
  • the X-ray powder diffraction of the crystal form A has a 2 ⁇ value of 16.4° ⁇ 0.2°, 18.4 ⁇ 0.2°, 22.4° ⁇ 0.2° at one or two or three places. Characteristic peaks.
  • the X-ray powder diffraction of the crystal form A has characteristic peaks at 2 ⁇ values of 16.4° ⁇ 0.2°, 18.4° ⁇ 0.2° and 22.4° ⁇ 0.2°.
  • the X-ray powder diffraction of the crystal form A has 2 ⁇ values of 6.8° ⁇ 0.2°, 11.7° ⁇ 0.2°, 13.6° ⁇ 0.2°, 16.4° ⁇ 0.2°, 17.1° ⁇ 0.2° Any 4, or 5, or 6, or 7, or 8, or 9 of 0.2°, 18.4° ⁇ 0.2°, 20.5° ⁇ 0.2°, 22.1° ⁇ 0.2°, 22.4° ⁇ 0.2° There are characteristic peaks.
  • the X-ray powder diffraction of the crystal form A has 2 ⁇ values of 6.8° ⁇ 0.2°, 11.7° ⁇ 0.2°, 13.6° ⁇ 0.2°, 16.4° ⁇ 0.2°, 17.1° ⁇ 0.2° There are characteristic peaks at 0.2°, 18.4° ⁇ 0.2°, 20.5° ⁇ 0.2°, 22.1° ⁇ 0.2° and 22.4° ⁇ 0.2°.
  • the X-ray powder diffraction pattern of the crystal form A is shown in FIG. 1 .
  • the positive solvent includes ketones, cyclic ethers, alkyl nitrile or heteronitrogen-based solvents
  • the anti-solvent includes alkanes, alcohols or pure water.
  • the ketone solvent is acetone
  • the cyclic ether solvent is tetrahydrofuran.
  • the alkyl nitrile solvent is acetonitrile.
  • the hetero-nitrogen-based solvent is dimethyl sulfoxide.
  • the alkane solvent is n-hexane.
  • the alcoholic solvent is isopropanol.
  • the penetration time is 1 to 14 days, eg 7 days
  • the alcohol solvent is methanol.
  • the high temperature is 40°C to 60°C, for example 50°C.
  • the crystallization temperature is -20°C to 5°C.
  • the cooling rate is 0.05°C/min to 0.5°C/min, eg 0.1°C/min.
  • the positive solvent includes cyclic ethers, heteronitrogens or alkyl nitriles
  • the anti-solvent includes pure water, alkanes, aromatic hydrocarbons or halogenated hydrocarbons.
  • the cyclic ethers include tetrahydrofuran and 2-methyltetrahydrofuran, the heteronitrogens are dimethyl sulfoxide, and the alkyl nitriles are acetonitrile.
  • the alkanes are n-heptane
  • the aromatic hydrocarbons are toluene
  • the halogenated hydrocarbons include dichloromethane and chloroform.
  • the temperature of dissolving, adding, stirring and precipitation is 5°C to 50°C, preferably 20°C to 30°C.
  • the organic solvent includes single or mixed solvents of alcohols, ketones, esters, halogenated hydrocarbons, cyclic ethers or alkyl nitriles.
  • the alcohols include methanol, ethanol and isopropanol
  • the ketones include methyl isobutyl ketone and acetone
  • the esters include ethyl acetate and isopropyl acetate
  • the The halogenated hydrocarbons include methylene chloride and chloroform
  • the cyclic ethers include tetrahydrofuran, 2-methyltetrahydrofuran and 1,4-dioxane
  • the alkyl nitriles are acetonitrile.
  • the mixed solvent includes acetonitrile and ethanol, acetone and methyl tert-butyl ether, tetrahydrofuran and water, acetone and chloroform, tetrahydrofuran and methyl tert-butyl ether, acetonitrile and dichloromethane, Acetone and isopropanol, acetonitrile and methyl tert-butyl ether.
  • the volume ratio of acetonitrile and ethanol is 1:4.
  • the volume ratio of the acetone to methyl tert-butyl ether is 1:4.
  • the volume ratio of tetrahydrofuran and water is 1:4.
  • the volume ratio of the acetone and chloroform is 1:0.1-8.
  • the volume ratio of tetrahydrofuran and methyl tert-butyl ether is 1:0.1-8.
  • the volume ratio of the acetonitrile and dichloromethane is 1:0.1-8.
  • the volume ratio of the acetone and isopropanol is 1:0.1-18.
  • the volume ratio of the acetonitrile to methyl tert-butyl ether is 1:0.1-18.
  • the volatilization and precipitation temperature is 20°C to 30°C.
  • the X-ray powder diffraction of the crystal form B has one or two or three 2 ⁇ values of 11.5° ⁇ 0.2°, 13.6° ⁇ 0.2°, 20.5° ⁇ 0.2° There are characteristic peaks.
  • the X-ray powder diffraction of the crystal form B has characteristic peaks at 2 ⁇ values of 11.5° ⁇ 0.2°, 13.6° ⁇ 0.2°, and 20.5° ⁇ 0.2°.
  • the X-ray powder diffraction of the crystal form B has one or two or three 2 ⁇ values of 15.6° ⁇ 0.2°, 21.5° ⁇ 0.2°, 22.7° ⁇ 0.2° There are characteristic peaks.
  • the X-ray powder diffraction of the crystal form B has characteristic peaks at 2 ⁇ values of 15.6° ⁇ 0.2°, 21.5° ⁇ 0.2°, and 22.7° ⁇ 0.2°.
  • the X-ray powder diffraction of the crystal form B has 2 ⁇ values of 6.8° ⁇ 0.2°, 11.5° ⁇ 0.2°, 13.6° ⁇ 0.2°, 14.5° ⁇ 0.2°, 15.6° ⁇ 0.2° Any 4, or 5, or 6, or 7, or 8, or 9 of 0.2°, 20.5° ⁇ 0.2°, 21.5° ⁇ 0.2°, 22.7° ⁇ 0.2°, 23.2° ⁇ 0.2° There are characteristic peaks.
  • the X-ray powder diffraction of the crystal form B has 2 ⁇ values of 6.8° ⁇ 0.2°, 11.5° ⁇ 0.2°, 13.6° ⁇ 0.2°, 14.5° ⁇ 0.2°, 15.6° ⁇ 0.2° There are characteristic peaks at 0.2°, 20.5° ⁇ 0.2°, 21.5° ⁇ 0.2°, 22.7° ⁇ 0.2° and 23.2° ⁇ 0.2°.
  • the X-ray powder diffraction pattern of the crystal form B is shown in FIG. 5 .
  • the ketone solvent is acetone
  • the volatilization and precipitation temperature is 20°C to 30°C.
  • the ketone solvent is acetone
  • the dissolution and precipitation temperature is 20°C to 30°C.
  • the penetration time is 1 to 4 weeks, eg 2 weeks.
  • said compound of formula (I) as starting material refers to its solid (crystalline or amorphous), semi-solid, wax or oil form.
  • the compound of formula (I) as starting material is in the form of a solid powder.
  • the "stirring" is accomplished by conventional methods in the art, such as magnetic stirring or mechanical stirring, and the stirring speed is 50-1800 rev/min, wherein the magnetic stirring is 200-1500 rev/min, preferably 300-1000 rev/min , the mechanical stirring is preferably 100 to 300 rpm.
  • the above crystals of the present invention can be used to prepare pharmaceutical compositions, which contain the above crystals of the present invention and a pharmaceutically acceptable carrier.
  • the above crystals of the present invention can be used to prepare a pharmaceutical composition with CAM activity, which comprises the above crystals of the present invention (forms A and B of the compound of formula (I)) as effective Element.
  • the above crystals of the present invention can be used to prepare a preventive or therapeutic drug for hepatitis B virus infection, which comprises the above-mentioned crystals of the present invention (formula (I) compound crystal form A, B) B) as an active ingredient.
  • the present invention also provides a pharmaceutical composition, which comprises any one of the above-mentioned crystals of the present invention (crystal forms A and B of the compound of formula (I)) and a pharmaceutically acceptable carrier.
  • the present invention also provides a pharmaceutical composition with CAM activity, which contains any one of the above-mentioned crystals of the present invention (crystal forms A and B of the compound of formula (I)) as an active ingredient.
  • the present invention provides a preventive or therapeutic drug for hepatitis B virus infection, which contains any one of the crystals of the present invention (forms A and B of the compound of formula (I)) as an active ingredient.
  • crystalline or “polymorphic form” means as evidenced by the characterization of the X-ray diffraction pattern shown.
  • X-ray diffraction patterns generally vary with the conditions of the instrument.
  • the relative intensities of X-ray diffraction patterns may also vary with experimental conditions, so the order of peak intensities cannot be used as the sole or decisive factor.
  • the relative intensities of the diffraction peaks in the X-ray diffraction pattern are related to the preferred orientation of the crystals, and the peak intensities shown here are illustrative and not for absolute comparison.
  • the experimental error of the peak angle is usually 5% or less, and the error of these angles should also be taken into account, and an error of ⁇ 0.2° is usually allowed.
  • the overall shift of the peak angle will be caused, and a certain shift is usually allowed.
  • the X-ray diffraction pattern of a crystal form in the present invention does not necessarily have to be exactly the same as the X-ray diffraction pattern in the examples mentioned here, and the "same X-ray diffraction pattern" mentioned herein does not mean absolutely identical, identical peak positions may differ by ⁇ 0.2° and some variability in peak intensity is allowed. Any crystalline form having the same or similar pattern as the characteristic peaks in these patterns is within the scope of the present invention.
  • Those skilled in the art can compare the patterns listed in the present invention with a pattern of an unknown crystal form to confirm whether the two sets of patterns reflect the same or different crystal forms.
  • the crystal forms A, B of the present invention are pure, single, and substantially not mixed with any other crystal forms.
  • substantially free when used to refer to a new crystal form means that the crystal form contains less than 20% by weight of other crystal forms, especially less than 10% by weight of other crystal forms, and even less More than 5% (weight) of other crystal forms, more than 1% (weight) of other crystal forms.
  • the numerical values and numerical ranges mentioned in the present invention should not be narrowly construed as numerical values or numerical ranges themselves, and those skilled in the art should understand that they may vary according to specific technical environments, without departing from the spirit and scope of the present invention. There are fluctuations around specific numerical values on the basis of principles. In the present invention, such a range of fluctuations that can be foreseen by those skilled in the art is often represented by the term "about”.
  • room temperature generally refers to 22°C to 28°C unless otherwise specified.
  • the X-ray powder diffraction patterns of the present invention were collected on Empyrean and X'Pert 3 X-ray powder diffractometers of Panalytical Corporation.
  • the method parameters of X-ray powder diffraction of the present invention are as follows:
  • the differential scanning calorimetry analysis diagram of the present invention is collected on the Q200 type and Discovery DSC 2500 type differential scanning calorimeter of TA company.
  • the method parameters of the differential scanning calorimetry analysis of the present invention are as follows:
  • thermogravimetric analysis diagram of the present invention is collected on the Discovery TGA 5500 type and Q5000 type thermogravimetric analyzer of TA company.
  • the method parameters of the thermogravimetric analysis of the present invention are as follows:
  • the hydrogen nuclear magnetic resonance spectrum data ( 1 H NMR) of the present invention was collected from a Bruker Avance II DMX 400M HZ nuclear magnetic resonance spectrometer. Weigh 1-5 mg of the sample, dissolve it with 0.5 mL of deuterated dimethyl sulfoxide, and prepare a solution of 2-10 mg/mL for testing.
  • the obtained solid samples were tested by XRPD, TGA, DSC, and 1 H NMR.
  • the obtained XRPD, TGA, DSC, and 1 H NMR data are shown in Figures 1 to 4, respectively, and the X-ray powder diffraction data are shown in Table 1.
  • XRPD results showed that the obtained samples were at about 6.8° ⁇ 0.2°, about 11.7° ⁇ 0.2°, about 13.6° ⁇ 0.2°, about 16.4° ⁇ 0.2°, about 17.1° ⁇ 0.2°, about 18.4° ⁇ 0.2°, about 20.5°
  • TGA shows that the sample will lose about 1% weight when heated to 200°C.
  • DSC data show that the melting point of Form A is around 221°C. Based on the characterization data, it is speculated that Form A is an anhydrous crystal.
  • the sample was transferred to -20°C and left to stand for about 1 day, and no solid was precipitated.
  • the sample was transferred to room temperature and volatilized until the solid was precipitated, and crystal form A was obtained.
  • Table 11 The detailed test conditions involved in this example are shown in Table 11, and the X-ray powder diffraction data of the sample of Example 25 are shown in Table 12.
  • Example 30 Weigh 14.7 mg of the solid compound of formula (I) obtained in Preparation Example 1 into a 3.0-ml glass vial at room temperature, and place the open mouth in a 20-ml glass vial prefilled with 4 ml of acetone. After sealing, put it at room temperature for gas-solid permeation for two days to obtain a clear solution, which was volatilized at room temperature until the solid was precipitated to obtain crystal form B, whose X-ray powder diffraction data are shown in Table 15.
  • Example 31 Weigh 14.7 mg of the solid compound of formula (I) obtained in Preparation Example 1 into a 3.0 mL glass vial at room temperature, and add 0.5 mL of acetone to dissolve the solid. Filter the sample solution into a new 3 mL glass vial using a 0.45 micron pore size Teflon filter. After sealing with parafilm, four pinholes were pricked on it, and then slowly volatilized at room temperature until a solid was precipitated to obtain crystal form B, and its X-ray powder diffraction data are shown in Table 16.
  • the sample is at about 6.8° ⁇ 0.2°, about 11.5° ⁇ 0.2°, about 13.6° ⁇ 0.2°, about 14.5° ⁇ 0.2°, about 15.6° ⁇ 0.2°, about 20.5° ⁇ 0.2°, about 21.5° ⁇ 0.2°.
  • the crystal form A and crystal form B of the present invention are respectively added into SGF (simulated artificial gastric fluid), FaSSIF (artificial intestinal fluid in fasting state), FeSSIF (artificial intestinal fluid in satiety state) and pure water, and are prepared into a suspension liquid. After equilibration for 1 hour, 2 hours, 4 hours and 24 hours, filter to obtain a saturated solution. The content of the sample in the saturated solution was determined by high performance liquid chromatography (HPLC). The test results are shown in Table 18, and the solubility curves are shown in Figures 9 to 12, respectively. The test results show that the crystal form A and the crystal form B of the present invention have higher solubility in SGF, FaSSIF, FeSSIF and pure water.
  • Moisture gain is less than 15% but not less than 2%
  • wet weight gain is less than 2% but not less than 0.2%
  • wet weight gain is less than 0.2%
  • crystal form A and crystal form B of the present invention were weighed, placed on glass slides respectively, a little vacuum silicone oil was added dropwise to disperse the samples, then covered with a cover glass and placed under a polarizing microscope for observation.
  • the crystal form A and the crystal form B of the present invention have better crystal habits.
  • crystal form A and crystal form B of the present invention have relatively uniform particle size distribution.

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Abstract

L'invention concerne des formes cristallines se rapportant à des composés sulfamoyle pyrrole amide et leurs procédés de préparation. L'invention concerne en particulier deux formes cristallines A et B de composés de formule (I) ainsi que leurs procédés de préparation et leurs utilisations. Les formes cristallines A et B des composés de formule (I) présentent des avantages pour au moins un aspect concernant la solubilité, le point de fusion, la stabilité, la dissolution, l'hygroscopicité, l'adhérence, la fluidité, la biodisponibilité, l'aptitude au traitement, l'effet de purification, la production de la préparation, la sécurité, etc., elles procurent un nouveau choix et un meilleur choix pour la préparation de formulations pharmaceutiques comprenant les composés de formule (I), et sont d'une grande importance pour le développement de médicaments.
PCT/CN2022/084300 2021-03-31 2022-03-31 Formes cristallines de composés sulfamoyle pyrrole amide et leurs procédés de préparation Ceased WO2022206879A1 (fr)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105452220A (zh) * 2013-05-17 2016-03-30 爱尔兰詹森科学公司 氨磺酰基吡咯酰胺衍生物及其作为药物用于治疗乙型肝炎的用途
WO2020016427A1 (fr) * 2018-07-19 2020-01-23 Ospedale San Raffaele S.R.L. Inhibiteurs du virus de l'hépatite b
WO2020030781A1 (fr) * 2018-08-10 2020-02-13 Ospedale San Raffaele S.R.L. Inhibiteurs tricycliques du virus de l'hépatite b

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105452220A (zh) * 2013-05-17 2016-03-30 爱尔兰詹森科学公司 氨磺酰基吡咯酰胺衍生物及其作为药物用于治疗乙型肝炎的用途
WO2020016427A1 (fr) * 2018-07-19 2020-01-23 Ospedale San Raffaele S.R.L. Inhibiteurs du virus de l'hépatite b
WO2020030781A1 (fr) * 2018-08-10 2020-02-13 Ospedale San Raffaele S.R.L. Inhibiteurs tricycliques du virus de l'hépatite b

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