Solid Forms Of Zanubrutinib And Its Process

DESC:INTRODUCTION Aspects of the present application relate to co-crystal of Zanubrutinib and its process for the preparation. The drug compound having the adopted name “Zanubrutinib” has chemical name: (S)-7-(1-acryloylpiperidin-4-yl)-2-(4-phenoxyphenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide of formula (I) as below. Formula (I) Zanubrutinib is a Bruton’s tyrosine kinase (BTK) inhibitor developed and marketed by BeiGene Co Ltd as BRUKINSA™ oral capsule for the treatment for the treatment of adult patients with mantle cell lymphoma (MCL) who have received at least one prior therapy in U.S. Moreover, this indication is approved under accelerated approval based on overall response rate. The US 9447106 B2 patent first disclosed Zanubrutinib generically and specifically and its use thereof for the treatment of mantle cell lymphoma (MCL). US 9447106 B2 further discloses a general procedure for the preparation of Zanubrutinib in Example-11. Subsequently, the US 20190169201A1 patent application discloses a crystalline form of Zanubrutinib characterized by XRD, MP, DSC and TGA. Also covers crystalline form of Zanubrutinib intermediate. The US 20190169201A1 patent application discloses alternate procedure for the preparation of Zanubrutinib and its intermediates. It also discloses the process for the preparation of crystalline form (Form A) of Zanubrutinib comprises the steps of dissolving Zanubrutinib in DCM, 3 swapping to solvent ??, recrystallizing from ??/???? to obtain Zanubrutinib crystalline form (Form A). The US 20190169201A1 patent application further discloses that Zanubrutnib was found to be an amorphous form according to the preparation in Product patent (US9447106B2), which was further confirmed by the X-Ray Powder Diffraction pattern of FIG. 7?. Different forms of Active pharmaceutical ingredients (API) in pharmaceutical compositions can be prepared. For example, API may be prepared in amorphous form, crystalline forms, solvate or hydrate and salt form. This variation in solid forms may be significant and may result in differences in pharmaceutical products with respect to solubility, bioavailability, stability and other properties. Accordingly, variation of the crystalline state of Zanubrutinib is one way in which physical properties of the Zanubrutinib. It has now been found that new solid state form i.e., co-crystals of Zanubrutinib can be obtained which may modify the properties of Zanubrutinib as compared to traditional solid forms such as salts, polymorphs, hydrates, solvates etc. SUMMARY In the first aspect, the present application provides a co-crystal of Zanubrutinib comprising Zanubrutinib with oxalic acid, designated as a crystalline form ZOX-1 of Zanubrutinib, characterized by a PXRD pattern comprising the peaks at about 4.00, 8.06, 11.49 and 19.35 ± 0.2° 2?. In an embodiment, the application provides a crystalline form ZOX-1 of Zanubrutinib with oxalic acid, characterized by a PXRD having additional peaks at about 20.36, 22.73 and 30.06 ± 0.2° 2?. 4 In the second aspect, the present application provides a process for preparation of co-crystals of Zanubrutinib (Crystalline form ZOX-1), comprising: a) providing solution of oxalic acid and Zanubrutinib in a solvent; b) optionally, heating the solution of step a); c) isolating co-crystals of Zanubrutinib (Crystalline form ZOX-1). In the third aspect, the present application provides a pharmaceutical composition comprising crystalline Form ZOX-1 of Zanubrutinib with oxalic acid with at least one pharmaceutically acceptable excipient. BRIEF DESCRIPTION OF THE DRAWING Figure 1 is an illustrative X-ray powder diffraction of crystalline Form ZOX-1 of Zanubrutinib with oxalic acid prepared by the method of Example-1. DETAILED DESCRIPTION Aspects of the present application relate to solid forms of Zanubrutinib and pharmaceutical compositions of thereof. Specific aspects relate to the crystalline forms of Zanubrutinib with oxalic acid. Further, aspects of the application relate to processes for the preparation of said solid form. In the first aspect, the present application provides a co-crystal of Zanubrutinib comprising Zanubrutinib with oxalic acid, designated as a crystalline form ZOX-1 of Zanubrutinib, characterized by a PXRD pattern comprising the peaks at about 4.00, 8.06, 11.49 and 19.35 ± 0.2° 2?. In an embodiment, the application provides a crystalline form ZOX-1 of Zanubrutinib with oxalic acid, characterized by a PXRD having additional peaks at about 20.36, 22.73 and 30.06 ± 0.2° 2?. In an embodiment, the application provides crystalline Form ZOX-1 of Zanubrutinib with oxalic acid, characterized by a PXRD pattern of figure 1. In the second aspect, the present application provides a process for 5 preparation of co-crystals of Zanubrutinib (Crystalline form ZOX-1), comprising: a) providing solution of oxalic acid and Zanubrutinib in a solvent; b) optionally, heating the solution of step a); c) isolating co-crystals of Zanubrutinib (Crystalline form ZOX-1). Suitable solvent that may be used in step (a) include, but are not limited to water, alcohol solvents, such as, for example, methanol, ethanol, isopropanol or the like; aromatic hydrocarbon solvents, such as, for example, toluene, xylene, chlorobenzene, tetralin or the like; ketone solvents such as acetone, methyl ethyl ketone, diethyl ketone, methyl isopropyl ketone, methyl isobutyl ketone or the like; ether solvents, such as, for example, diethyl ether, diisopropyl ether, tert-butyl methyl ether, dibutyl ether, tetrahydrofuran, 1,2-dimethoxyethane, 2-methoxyethanol, 2-ethoxy ethanol, anisole, 1, 4-dioxane, or the like; alkanes, such as for example, n-pentane, n-heptane, n-hexane, nheptane or the like; chlorinated hydrocarbon solvents, such as chloroform, dichloromethane or mixtures thereof. Optionally, the solution obtained above may be filtered to remove any insoluble particles. The insoluble particles may be removed suitably by filtration, centrifugation, decantation, or any other suitable techniques. The solution may be filtered by passing through paper, glass fiber, or other membrane material, or a bed of a clarifying agent such as celite or hyflow. Depending upon the equipment used the concentration and temperature of the solution, the filtration apparatus may need to be preheated to avoid premature crystallization. The temperature at which the above steps may be carried out in between about 20 °C and about 100 °C, preferably at about 25°C and about 60°C. The isolation of step c) can be effected, if desired, by any suitable separation methods such as precipitation, filtration, centrifugation, extraction, acid-base treatment, by scraping, or by shaking the container conventional isolation and refining means such as concentration, concentration under 6 reduced pressure or by a combination of these procedures. Drying in the embodiments of the present invention may be suitably carried out by using any of an air tray dryer, vacuum tray dryer, fluidized bed dryer, spin flash dryer, flash dryer, and the like. The drying may be carried out at atmospheric pressure or above, or under reduced pressures, specifically at temperatures less than about 80 °C and more specifically less than about 60 °C. The drying may be carried out for any time period required for obtaining a desired product quality, such as from about 30 minutes to about 24 hours, or longer. All PXRD data reported herein are obtained using a PANalytical X-ray Diffractometer and Bruker D8 advance X-ray Diffractometer with copper Ka radiation. Starting material may be either in a crystalline or amorphous state or an alternate crystalline form of Zanubrutinib known in the art. In the third aspect, the present application provides a pharmaceutical composition comprising crystalline Form ZOX-1 of Zanubrutinib with oxalic acid with at least one pharmaceutically acceptable excipient. In another aspect, the present application provides solid forms of Zanubrutinib with oxalic acid selected from crystalline form ZOX-1 according to instant application and pharmaceutical compositions thereof, wherein the chemical purity of Zanubrutinib may be more than 99% by HPLC or more than 99.5% by HPLC Certain specific aspects and embodiments of the present application will be explained in greater detail with reference to the following examples, which are provided only for purposes of illustration and should not be construed as limiting the scope of the application in any manner. Variations of the described procedures, as will be apparent to those skilled in the art, are intended to be within the scope of the present application. Definitions The term "about" when used in the present application preceding a number and 7 referring to it, is meant to designate any value which lies within the range of ±10%, preferably within a range of ±5%, more preferably within a range of ±2%, still more preferably within a range of ±1 % of its value. For example "about 10" should be construed as meaning within the range of 9 to 11 , preferably within the range of 9.5 to 10.5, more preferably within the range of 9.8 to 10.2, and still more preferably within the range of 9.9 to 10.1. EXAMPLES Example-1: Preparation of co-crystal of Zanubrutinib with Oxalic acid. Zanubrutinib (3 g) and oxalic acid (573 mg) were dissolved in toluene (50 mL) at 30°C. The mixture was stirred at 50°C for 15 minutes and the resultant solution was filtered to make it particle free. The obtained clear solution was cooled to 30°C. Filtered the obtained solid and washed heptane (10 mL) and kept under suction for 10 minutes to obtain the title compound. PXRD: Crystalline Form ZOX-1 (Figure 1). ,CLAIMS:CLAIMS 1. A co-crystal of Zanubrutinib comprising Zanubrutinib with oxalic acid, characterized by a PXRD pattern comprising the peaks at about 4.00, 8.06, 11.49 and 19.35 ± 0.2° 2?. 2. Co-crystal of Zanubrutinib with oxalic acid according to claim 1, characterized by a PXRD pattern of figure 1. 3. A process for preparation of co-crystals of Zanubrutinib comprising: a) providing a solution of oxalic acid and Zanubrutinib in a solvent; b) optionally, heating the solution of step a); c) isolating co-crystals of Zanubrutinib (Crystalline form ZOX-1). 4. The process according to claim 3, wherein the solvent is aromatic hydrocarbons. 5. The process according to claim 4, wherein the solvent is toluene.