WO2016150349A1 - 一种pci-32765晶型a的制备方法 - Google Patents
一种pci-32765晶型a的制备方法 Download PDFInfo
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- WO2016150349A1 WO2016150349A1 PCT/CN2016/076779 CN2016076779W WO2016150349A1 WO 2016150349 A1 WO2016150349 A1 WO 2016150349A1 CN 2016076779 W CN2016076779 W CN 2016076779W WO 2016150349 A1 WO2016150349 A1 WO 2016150349A1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
- C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- 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
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N23/00—Investigating or analysing materials by the use of wave or particle radiation, e.g. X-rays or neutrons, not covered by groups G01N3/00 – G01N17/00, G01N21/00 or G01N22/00
- G01N23/20—Investigating or analysing materials by the use of wave or particle radiation, e.g. X-rays or neutrons, not covered by groups G01N3/00 – G01N17/00, G01N21/00 or G01N22/00 by using diffraction of the radiation by the materials, e.g. for investigating crystal structure; by using scattering of the radiation by the materials, e.g. for investigating non-crystalline materials; by using reflection of the radiation by the materials
- G01N23/20075—Investigating or analysing materials by the use of wave or particle radiation, e.g. X-rays or neutrons, not covered by groups G01N3/00 – G01N17/00, G01N21/00 or G01N22/00 by using diffraction of the radiation by the materials, e.g. for investigating crystal structure; by using scattering of the radiation by the materials, e.g. for investigating non-crystalline materials; by using reflection of the radiation by the materials by measuring interferences of X-rays, e.g. Borrmann effect
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N25/00—Investigating or analyzing materials by the use of thermal means
- G01N25/20—Investigating or analyzing materials by the use of thermal means by investigating the development of heat, i.e. calorimetry, e.g. by measuring specific heat, by measuring thermal conductivity
- G01N25/48—Investigating or analyzing materials by the use of thermal means by investigating the development of heat, i.e. calorimetry, e.g. by measuring specific heat, by measuring thermal conductivity on solution, sorption, or a chemical reaction not involving combustion or catalytic oxidation
- G01N25/4846—Investigating or analyzing materials by the use of thermal means by investigating the development of heat, i.e. calorimetry, e.g. by measuring specific heat, by measuring thermal conductivity on solution, sorption, or a chemical reaction not involving combustion or catalytic oxidation for a motionless, e.g. solid sample
- G01N25/4866—Investigating or analyzing materials by the use of thermal means by investigating the development of heat, i.e. calorimetry, e.g. by measuring specific heat, by measuring thermal conductivity on solution, sorption, or a chemical reaction not involving combustion or catalytic oxidation for a motionless, e.g. solid sample by using a differential method
Definitions
- the invention relates to the field of medical chemistry, in particular to a preparation method of PCI-32765 crystal form A.
- PCI-32765 (a compound of formula I) was developed by the US biopharmaceutical company Pharmacyclics, and on November 13, 2013, the US Food and Drug Administration (FDA) approved a single therapeutic drug for mantle cell lymphoma, also known as Ibrutinib.
- BTK Bruton's tyrosine kinase
- Patent CN104327085A discloses a pharmaceutically useful new crystalline form of PCI-32765, designated Form A, which also discloses a Form A preparation process. This method is a small-scale preparation method, and so far, a stable and reliable method for preparing crystal form A by amplification has not been seen.
- a method for preparing PCI-32765 crystal form A comprising the following steps:
- step 1) The solution in the step 1) is added dropwise to the anti-solvent, and after the addition is completed, the solution is stirred at a temperature of 0 to 20 ° C, and the seed crystal of PCI-32765 crystal form A is added, or the step 1) The solution is added dropwise to a suspension containing PCI-32765 crystal form A seed crystal at a temperature of 0 to 20 ° C;
- step 2) controlling the step 2) to obtain a solution system which is continuously stirred and matured until the crystal transformation is completed to obtain a crystal slurry;
- positive solvent may be a single solvent or a mixed solvent, and in the present invention means a single solvent or a mixed solvent which is soluble in PCI-32765 free base.
- the positive solvent is methanol or a mixed solvent containing methanol.
- the mixed solvent is methanol and dimethyl sulfoxide in a volume ratio of 1:0.8 to 1.2.
- the PCI-32765 free base solution is formulated at 10 to 50 °C.
- anti-solvent has its ordinary meaning in the art, and in the present invention means a solvent in which PCI-32765 Form A is added to a solvent to cause precipitation.
- the anti-solvent is pure water.
- the mass ratio of the seed crystal of PCI-32765 crystal form A described in step 2) to the mass ratio of PCI-32765 free base described in step 1) is from 0.01 to 0.1:1.
- the ratio of the feed volume of the positive solvent to the mass ratio of the PCI-32765 free base is 10 to 40 mL/g.
- the feed volume of the anti-solvent described in step 2) and the charge-to-mass ratio of PCI-32765 free base described in step 1) are from 30 to 80 mL/g.
- step 2) the solution in the step 1) is added dropwise to the anti-solvent or the suspension at a rate of 1 to 30 mL/min.
- the temperature conditions described in step 2) are from 0 to 10 °C.
- the temperature condition described in step 2) is 0 to 5 °C.
- the temperature of the ripening described in step 3) is from 0 to 40 °C.
- the temperature of the ripening described in the step 3) is 0 to 30 °C.
- the ripening temperature is 0 to 20 °C.
- the ripening time described in step 3) is from 5 to 48 hours.
- the ripening time described in step 3) is 5 to 24 hours.
- the ripening time described in step 3 is from 14 to 20 hours.
- the specific method of the step 3) is: controlling the solution system obtained in the step 2) to continue stirring, and then curing at a constant temperature of 0 to 5 ° C for 15 to 24 hours; or, the solution system obtained in the step 2) is 0 to 0. After maintaining at 5 ° C for 1 to 3 hours, the temperature is raised to 10 to 20 ° C, and maintained at 10 to 20 ° C for 10 to 15 hours to obtain a crystal slurry.
- the washing solvent used in step 4) is pure water.
- the drying conditions in step 4) are controlled as follows: The washed sample is placed in a vacuum oven at 30-50 ° C and dried to a constant weight of the sample.
- the preparation method of the crystal form A provided by the invention has the characteristics of simple process operation, stable and controllable process, high yield, environmental friendliness and good impurity removal ability, and the prepared crystal form A can be stably stored, wettability and solubility are consistent. Medicinal requirements.
- the preparation method of the crystal form A provided by the invention breaks through the bottleneck of the prior art which is difficult to scale production, and solves the problem of industrial production.
- Figure 1 is an X-ray powder diffraction pattern of PCI-32765 Form A
- Figure 3 is a thermogravimetric analysis diagram of PCI-32765 crystal form A
- the preparation method of the crystal form A provided by the invention has the advantages of simple process operation, stable and controllable process, high yield, environmental friendliness, good impurity removal ability, and the prepared crystal form A can be stably stored, hygroscopicity and solubility are in accordance with the medicinal use. Claim.
- the starting material used in the present invention is a crude product of PCI-32765 free base, which is obtained by commercially available means, and the test method is usually carried out according to conventional conditions or conditions recommended by the manufacturer.
- the room temperature is usually 25 °C.
- the X-ray powder diffraction pattern of the present invention was collected on a Panalytical Empyrean X-ray powder diffractometer.
- the method parameters of the X-ray powder diffraction described in the present invention are as follows:
- Scan range: from 3.0 to 40.0 degrees
- the differential scanning calorimetry (DSC) map of the present invention was acquired on a TA Q2000.
- the method parameters of the differential scanning calorimetry (DSC) described in the present invention are as follows:
- thermogravimetric analysis (TGA) map of the present invention was taken on a TA Q5000.
- the method parameters of the thermogravimetric analysis (TGA) described in the present invention are as follows:
- PCI-32765 Form A Three batches of PCI-32765 Form A were produced as follows.
- step 3 The solution of PCI-32765 free base in the step 1) was added dropwise to the suspension in the step 2) at a uniform rate for about 1 hour. After the completion of the dropwise addition, the mixture was maintained at 0 ° C for 2 hours, and then the crystal system was heated to 20 ° C in 4 hours. After the aging for 14 hours, a crystal slurry was obtained, and the crystal form of the product was sampled by XRPD and completely converted into Form A.
- the first batch described above having a scale of 35 g, obtained a solid product, weighed, had a mass of 35.4 g, a yield of 91.1%, and a purity of 100.0%.
- the product is tested by XRPD and is the crystal form A of PCI-32765.
- the second batch process was the same as the first batch, the scale was 50g, and the obtained solid product was weighed, the mass was 50.75g, the yield was 91.5%, and the purity was 99.8%.
- the product is tested by XRPD and is the crystal form A of PCI-32765.
- the third batch process was the same as the first batch, and the scale was 75 g of the obtained solid product, weighed, the mass was 75.2 g, the yield was 90.3%, and the purity was 99.7%.
- the product is tested by XRPD, which is PCI-32765. Form A.
- the X-ray powder diffraction data of the crystal form obtained in this example is shown in Table 1. Its XRPD diagram is shown in Figure 1, its DSC diagram is shown in Figure 2, and its TGA diagram is shown in Figure 3.
- PCI-32765 Form A Three batches of PCI-32765 Form A were produced as follows.
- the first batch described above had a scale of 50 g, and the obtained solid product was weighed, the mass was 48.4 g, the yield was 86.8%, and the purity was 99.9%.
- the product is tested by XRPD and is the crystal form A of PCI-32765.
- the second batch process was the same as the first batch, the scale was 5g, the obtained solid product was weighed, the mass was 4.8g, the yield was 86.0%, and the purity was 100.0%.
- the product is tested by XRPD and is the crystal form A of PCI-32765.
- the third batch process was the same as the first batch, the scale was 5g, the obtained solid product was weighed, the mass was 4.4g, the yield was 78.0%, and the purity was 100.0%.
- the product is tested by XRPD and is the crystal form A of PCI-32765.
- step 3 The solution of PCI-32765 free base in the step 1) was added dropwise to the suspension in the step 2) at a uniform rate for about 1 hour. After the completion of the dropwise addition, the mixture was maintained at 2 ° C for 1 hour, and then the crystal system was heated to 40 ° C in 1 hour. After aging for 16 hours, a crystal slurry was obtained, and the crystal form of the product was detected by XRPD and completely converted into crystal form A.
- the solid product obtained in the batch was weighed, the mass was 10.1 g, the yield was 91.1%, and the purity was 99.53%. It is detected by XRPD and is the crystal form A of PCI-32765.
- step 3 The solution of PCI-32765 free base in the step 1) was added dropwise to the suspension in the step 2) at a uniform rate for about 1 hour. After the completion of the dropwise addition, the mixture was maintained at 5 ° C for 1 hour, and then the crystal system was heated to 40 ° C in 1 hour. After the aging for 16 hours, the crystal slurry was sampled and the crystal form of the product was detected by XRPD, and the crystal form was completely converted.
- the solid product obtained in this batch was weighed and had a mass of 9.5 g, a yield of 94.9%, and a purity of 99.90%. It is detected by XRPD and is the crystal form A of PCI-32765.
- PCI-32765 Form A Two batches of PCI-32765 Form A were produced as follows.
- step 3 The solution of PCI-32765 free base in step 1) was added dropwise to the suspension in step 2) at a uniform rate for about 10 minutes. After the completion of the dropwise addition, the crystal slurry was obtained by maintaining at 0 ° C for 20 hours, and the sample was sampled by XRPD to detect the crystal form of the product, which was completely converted into the crystal form A.
- the scale is 1g
- the obtained solid product weighed
- the mass is 0.89g
- the yield is 79.0%
- purity is 100.0%. It is detected by XRPD and is the crystal form A of PCI-32765.
- the second batch process was the same as the first batch, the scale was 0.3 g, and the obtained solid product was weighed, the mass was 0.27 g, the yield was 80.0%, and the purity was 100.0%.
- the product is tested by XRPD and is the crystal form A of PCI-32765.
Abstract
Description
2theta | d间隔 | 相对强度% |
5.23 | 16.91 | 100.00 |
11.26 | 7.86 | 4.69 |
16.22 | 5.47 | 4.86 |
16.44 | 5.39 | 2.12 |
17.65 | 5.03 | 12.28 |
18.09 | 4.91 | 4.76 |
18.86 | 4.71 | 7.03 |
19.28 | 4.60 | 11.48 |
20.75 | 4.28 | 6.76 |
22.07 | 4.03 | 11.15 |
22.46 | 3.96 | 8.33 |
23.00 | 3.87 | 4.29 |
25.90 | 3.44 | 3.16 |
2theta | d间隔 | 相对强度% |
5.18 | 17.06 | 19.84 |
11.25 | 7.87 | 12.41 |
16.19 | 5.47 | 35.00 |
16.43 | 5.40 | 16.26 |
17.34 | 5.11 | 16.63 |
17.63 | 5.03 | 19.00 |
18.06 | 4.91 | 30.56 |
18.85 | 4.71 | 28.54 |
19.28 | 4.60 | 62.29 |
20.73 | 4.28 | 26.85 |
22.06 | 4.03 | 100.00 |
22.43 | 3.96 | 21.09 |
22.99 | 3.87 | 40.74 |
23.87 | 3.73 | 11.47 |
25.89 | 3.44 | 11.11 |
2theta | d间隔 | 相对强度% |
5.20 | 17.01 | 100.00 |
8.48 | 10.42 | 1.62 |
9.60 | 9.21 | 2.81 |
10.40 | 8.50 | 1.84 |
11.23 | 7.88 | 8.49 |
13.03 | 6.80 | 1.41 |
13.19 | 6.71 | 1.26 |
14.88 | 5.95 | 0.28 |
15.33 | 5.78 | 0.54 |
16.20 | 5.47 | 10.48 |
16.41 | 5.40 | 5.36 |
16.99 | 5.22 | 1.59 |
17.34 | 5.12 | 4.44 |
17.63 | 5.03 | 19.25 |
18.05 | 4.91 | 8.87 |
18.85 | 4.71 | 13.09 |
19.27 | 4.61 | 19.97 |
20.01 | 4.44 | 0.91 |
20.53 | 4.33 | 3.09 |
20.75 | 4.28 | 11.45 |
22.07 | 4.03 | 22.16 |
22.45 | 3.96 | 13.29 |
22.98 | 3.87 | 9.27 |
23.88 | 3.73 | 2.60 |
24.52 | 3.63 | 1.47 |
25.04 | 3.56 | 2.74 |
25.89 | 3.44 | 5.38 |
26.32 | 3.39 | 1.07 |
26.57 | 3.35 | 0.76 |
27.77 | 3.21 | 1.15 |
27.95 | 3.19 | 1.99 |
28.72 | 3.11 | 1.44 |
28.94 | 3.09 | 1.82 |
29.51 | 3.03 | 0.35 |
2theta | d间隔 | 相对强度% |
5.20 | 17.00 | 16.22 |
8.48 | 10.43 | 5.70 |
9.57 | 9.24 | 10.69 |
11.21 | 7.89 | 23.34 |
13.16 | 6.73 | 2.80 |
16.17 | 5.48 | 41.85 |
16.43 | 5.39 | 20.04 |
16.98 | 5.22 | 6.93 |
17.35 | 5.11 | 19.37 |
17.59 | 5.04 | 33.02 |
18.05 | 4.92 | 40.14 |
18.83 | 4.71 | 40.51 |
19.24 | 4.61 | 76.19 |
20.77 | 4.28 | 35.60 |
22.05 | 4.03 | 100.00 |
22.42 | 3.97 | 26.77 |
22.96 | 3.87 | 46.03 |
23.86 | 3.73 | 12.36 |
24.50 | 3.63 | 3.71 |
25.01 | 3.56 | 12.77 |
25.87 | 3.44 | 14.74 |
26.37 | 3.38 | 2.68 |
27.85 | 3.20 | 6.13 |
28.90 | 3.09 | 9.63 |
29.42 | 3.04 | 1.71 |
2theta | d间隔 | 相对强度% |
5.20 | 17.00 | 36.43 |
11.22 | 7.89 | 12.08 |
16.19 | 5.48 | 33.84 |
16.41 | 5.40 | 23.53 |
17.37 | 5.11 | 19.71 |
17.63 | 5.03 | 22.57 |
18.08 | 4.91 | 33.43 |
18.87 | 4.70 | 30.72 |
19.29 | 4.60 | 63.34 |
20.84 | 4.26 | 25.71 |
22.08 | 4.03 | 100.00 |
22.45 | 3.96 | 23.36 |
23.03 | 3.86 | 41.70 |
23.90 | 3.72 | 11.90 |
25.12 | 3.54 | 10.19 |
Claims (17)
- 一种PCI-32765晶型A的制备方法,其特征在于:包括以下步骤:1)PCI-32765游离碱溶液的配制:将PCI-32765的游离碱固体溶解于正溶剂中;2)将步骤1)中的溶液滴加到反溶剂中,滴加完毕后在0~20℃的温度条件下搅拌,并加入PCI-32765晶型A的晶种,或将步骤1)中的溶液在0~20℃的温度条件下滴加到含PCI-32765晶型A晶种的悬浊液中;3)控制步骤2)所得的溶液体系持续搅拌熟化至转晶完全,获得晶浆;4)步骤3)中所述晶浆,经过滤,洗涤,干燥后,得到PCI-32765晶型A的粉末。
- 根据权利要求1所述的制备方法,其特征在于:所述正溶剂为甲醇或含甲醇的混合溶剂。
- 根据权利要求2所述的制备方法,其特征在于:所述的混合溶剂为体积比为1∶0.8~1.2的甲醇和二甲亚砜。
- 根据权利要求1所述的制备方法,其特征在于:步骤1)中,在10~50℃下配制所述的PCI-32765游离碱溶液。
- 根据权利要求1所述的制备方法,其特征在于:所述反溶剂为纯水。
- 根据权利要求1所述的制备方法,其特征在于:步骤2)中所述的PCI-32765晶型A的晶种的投料质量与步骤1)中所述的PCI-32765游离碱投料质量比为0.01~0.1∶1。
- 根据权利要求1至3中任一项所述的制备方法,其特征在于:步骤1)中,所述的正溶剂的投料体积与所述的PCI-32765游离碱的投料质量比为10~40mL/g。
- 根据权利要求1或5所述的制备方法,其特征在于:步骤2)中所述的反溶剂的投料体积与步骤1)中所述的PCI-32765游离碱的投料质量比为30~80mL/g。
- 根据权利要求1所述的制备方法,其特征在于:步骤2)中,所述的步骤1)中的溶液滴加到所述的反溶剂或所述的悬浊液中的速度为1~30mL/min。
- 根据权利要求1所述的制备方法,其特征在于:步骤2)中所述的温度条件为0~10℃。
- 根据权利要求10所述的制备方法,其特征在于:步骤2)中所述的温度条件为0~5℃。
- 根据权利要求1所述的制备方法,其特征在于:步骤3)中所述的熟化的温度为0~40℃。
- 根据权利要求12所述的制备方法,其特征在于:步骤3)中所述的熟化的温度为0~30℃。
- 根据权利要求13所述的制备方法,其特征在于:步骤3)中所述的熟化的温度为0~20℃。
- 根据权利要求1所述的制备方法,其特征在于:步骤3)的具体方法为:控制步骤2)所得的溶液体系持续搅拌,然后在0~5℃下恒温熟化15~24小时;或者,将步骤2)所得的溶液体系在0~5℃维持1~3小时,然后升温至10~20℃,在10~20℃下维持10~15小时,获得晶浆。
- 根据权利要求1所述的制备方法,其特征在于:步骤4)中所用的洗涤溶剂为纯水。
- 根据权利要求1所述的制备方法,其特征在于:步骤4)中的干燥条件的控制如下:将洗涤过的样品放置于30~50℃的真空干燥箱中干燥至样品恒重。
Priority Applications (7)
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AU2016236578A AU2016236578B2 (en) | 2015-03-20 | 2016-03-18 | Preparation method of crystalline form a of pci-32765 |
CA2980418A CA2980418C (en) | 2015-03-20 | 2016-03-18 | Preparation method of crystalline form a of pci-32765 |
JP2017567523A JP6657269B2 (ja) | 2015-03-20 | 2016-03-18 | Pci―32765の結晶型aの調製方法 |
EP16767726.9A EP3272753B1 (en) | 2015-03-20 | 2016-03-18 | Preparation method of pci-32765 crystal form a |
MX2017011990A MX2017011990A (es) | 2015-03-20 | 2016-03-18 | Metodo de preparacion de la forma a cristalina de pci-32765. |
US15/559,777 US10138239B2 (en) | 2015-03-20 | 2016-03-18 | Preparation method of crystalline form a of PCI-32765 |
IL254530A IL254530A0 (en) | 2015-03-20 | 2017-09-17 | Preparation method of crystalline form a of pci-32765 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10183024B2 (en) | 2016-12-02 | 2019-01-22 | Apotex Inc. | Crystalline forms of ibrutinib |
EP3501609A1 (en) | 2017-12-08 | 2019-06-26 | Zentiva K.S. | Pharmaceutical compositions comprising ibrutinib |
WO2019195827A1 (en) | 2018-04-06 | 2019-10-10 | Johnson Matthey Public Limited Company | Novel form of ibrutinib |
EP3575300A1 (en) | 2018-05-31 | 2019-12-04 | Apotex Inc. | Novel crystalline forms of ibrutinib |
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CN106831788B (zh) * | 2017-01-22 | 2020-10-30 | 鲁南制药集团股份有限公司 | 伊布替尼精制方法 |
WO2019070698A1 (en) | 2017-10-02 | 2019-04-11 | Johnson Matthey Public Limited Company | NEW FORMS OF IBRUTINIB |
CN115639091B (zh) * | 2022-12-21 | 2023-03-17 | 南通嘉鹏新材料科技有限公司 | 一种聚酯热熔胶的硬度检测设备 |
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CN103121999A (zh) * | 2012-08-29 | 2013-05-29 | 苏州迪飞医药科技有限公司 | 一种酪氨酸激酶抑制剂pci-32765的合成方法 |
CN104327085A (zh) * | 2013-11-27 | 2015-02-04 | 苏州晶云药物科技有限公司 | Pci-32765的晶型a及其制备方法 |
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NZ702548A (en) * | 2012-06-04 | 2015-11-27 | Pharmacyclics Llc | Crystalline forms of a bruton’s tyrosine kinase inhibitor |
EP2914296B2 (en) * | 2012-11-01 | 2021-09-29 | Infinity Pharmaceuticals, Inc. | Treatment of cancers using pi3 kinase isoform modulators |
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CN103121999A (zh) * | 2012-08-29 | 2013-05-29 | 苏州迪飞医药科技有限公司 | 一种酪氨酸激酶抑制剂pci-32765的合成方法 |
CN104327085A (zh) * | 2013-11-27 | 2015-02-04 | 苏州晶云药物科技有限公司 | Pci-32765的晶型a及其制备方法 |
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US10183024B2 (en) | 2016-12-02 | 2019-01-22 | Apotex Inc. | Crystalline forms of ibrutinib |
EP3501609A1 (en) | 2017-12-08 | 2019-06-26 | Zentiva K.S. | Pharmaceutical compositions comprising ibrutinib |
WO2019195827A1 (en) | 2018-04-06 | 2019-10-10 | Johnson Matthey Public Limited Company | Novel form of ibrutinib |
EP3575300A1 (en) | 2018-05-31 | 2019-12-04 | Apotex Inc. | Novel crystalline forms of ibrutinib |
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EP3272753B1 (en) | 2020-03-04 |
EP3272753A4 (en) | 2018-07-25 |
AU2016236578B2 (en) | 2019-04-04 |
CN105669679A (zh) | 2016-06-15 |
US20180065958A1 (en) | 2018-03-08 |
IL254530A0 (en) | 2017-11-30 |
US10138239B2 (en) | 2018-11-27 |
JP6657269B2 (ja) | 2020-03-04 |
JP2018508584A (ja) | 2018-03-29 |
CA2980418A1 (en) | 2016-09-29 |
EP3272753A1 (en) | 2018-01-24 |
CA2980418C (en) | 2019-07-09 |
MX2017011990A (es) | 2018-06-06 |
AU2016236578A1 (en) | 2017-10-12 |
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