NZ776907B2 - New crystalline forms of a mcl-1 inhibitor, a process for their preparation and pharmaceutical compositions containing them. - Google Patents
New crystalline forms of a mcl-1 inhibitor, a process for their preparation and pharmaceutical compositions containing them.Info
- Publication number
- NZ776907B2 NZ776907B2 NZ776907A NZ77690719A NZ776907B2 NZ 776907 B2 NZ776907 B2 NZ 776907B2 NZ 776907 A NZ776907 A NZ 776907A NZ 77690719 A NZ77690719 A NZ 77690719A NZ 776907 B2 NZ776907 B2 NZ 776907B2
- Authority
- NZ
- New Zealand
- Prior art keywords
- compound
- crystalline form
- cancer
- expressed
- theta
- Prior art date
Links
Classifications
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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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Abstract
Crystalline forms of Compound A: (I) characterized by its X-ray powder diffraction diagram,solid-state 13C NMR spectrum, MIR spectrum and Raman spectrum and pharmaceutical compositions containing it.
Claims (21)
1. A crystalline Form M of 2-{[5-{3-Chloromethyl[2-(4-methylpiperazinyl) ethoxy]phenyl}(4-fluorophenyl)thieno[2,3-d]pyrimidinyl]oxy}(2-{[2-(2- methoxyphenyl)pyrimidinyl]methoxy}phenyl)propanoic acid (Compound A) 5 having an X-ray powder diffraction diagram showing at least the following diffraction lines (Bragg's angle 2 theta, expressed in degrees ± 0.2°): 8.94 and 18.24.
2. The crystalline Form M of Compound A according to claim 1 in substantially pure form.
3. The crystalline Form M of Compound A according to claim 1 or claim 2, having an X- 10 ray powder diffraction diagram which exhibits at least 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14 or all of the following diffraction lines (Bragg's angle 2 theta, expressed in degrees ± 0.2°): 6.27; 8.94; 9.09; 12.16; 13.67; 14.75; 15.06; 16.97; 17.22; 17.44; 18.24; 19.16; 19.93; 20.91; and 25.88.
4. The crystalline Form M of Compound A according to claim 3, having an X-ray 15 powder diffraction diagram which exhibits the following diffraction lines (Bragg's angle 2 theta, expressed in degrees ± 0.2°): 8.94; 13.67; 14.75; 17.22; 18.24.
5. The crystalline Form M of Compound A according to claim 3, having an X-ray powder diffraction diagram which exhibits the following diffraction lines (Bragg’s angle 2 theta, expressed in degrees ± 0.2°): 6.27; 8.94; 9.09; 12.16; 13.67; 14.75; 20 15.06; 16.97; 17.22; 17.44; 18.24; 19.16; 19.93; 20.91; and 25.88.
6. The crystalline Form M of Compound A according to claim 5, having the following X-ray powder diffraction diagram, expressed in terms of line position (Bragg's angle 2 theta, expressed in degrees ± 0.2°) and interplanar distance d (expressed in Å): Angle 2-theta Interplanar Line No. (degrees) distance (Å) 1 6.27 14.10 2 8.94 9.89 3 9.09 9.73 4 12.16 7.28 5 13.67 6.48 6 14.75 6.00 7 15.06 5.88 8 16.97 5.22 9 17.22 5.15 10 17.44 5.08 11 18.24 4.86 12 19.16 4.63 13 19.93 4.45 14 20.91 4.25 15 25.88 3.44
7. The crystalline Form M of Compound A according to any one of claims 1 to 6, having a solid-state C CP/MAS NMR spectrum which exhibits the following peaks (expressed in ppm ± 0.2 ppm): 175.1, 153.7, 134.8, 108.9, 71.4 and 35.1.
8. The crystalline Form M of Compound A according to any one of claims 1 to 6, having 5 a solid-state C CP/MAS NMR spectrum which exhibits the following peaks (expressed in ppm ± 0.2 ppm): 175.1, 168.5, 167.4, 164.6, 162.6, 157.5 , 156.3, 153.7, 135.5, 134.8, 130.4, 129.9, 128.4, 126.8, 120.9, 119.9, 118.5, 116.9, 112.5, 111.1, 108.9, 78.7, 71.4, 54.9, 42.1 , 35.1 and 18.2.
9. A pharmaceutical composition comprising as active ingredient crystalline Form M of 10 Compound A according to any one of claims 1 to 8 in combination with one or more pharmaceutically acceptable carrier, glidant, diluent, excipient or stabilizer.
10. A process for the preparation of crystalline Form M of Compound A according to any one of claims 1 to 8, wherein Compound A is crystallized in a solvent selected from toluene, 2-methyltetrahydrofuran, and a mixture of toluene and methyl tert-butyl ether.
11. The process of claim 10, wherein the Compound A, from which form M is 5 crystallized, is crystalline Form A of Compound A.
12. The process of claim 10 or 11, wherein the concentration of Compound A in the solvent is between 5 to 15 % m/m.
13. The process of any one of claims 10 to 12, wherein the process produces a slurry, which slurry is dried between 20 °C and 80 °C. 10
14. The process according to any one of claims 10 to 13, wherein the crystallization is seeded using 0.5% to 5% m/m of crystalline Form M of Compound A.
15. The process of any one of claims 10 to 14, wherein the crystallization is seeded at a temperature comprised between 20 °C and 60 °C.
16. Use of the crystalline Form M of Compound A according to any one of claims 1-8 in the manufacture of a medicament for reducing the symptoms of a condition selected from MCL-1 associated cancers, auto-immune diseases and diseases of the immune system in a subject need thereof.
17. The use of claim 16, wherein the cancer is selected from bladder cancer, brain cancer, breast cancer, cancer of the uterus, chronic lymphoid leukemias, colorectal cancer, esophagus cancer, liver cancer, lymphoblastic leukemias, acute myeloid leukemia, lymphomas, melanomas, malignant haemopathies, myelomas, ovarian cancer, non- small-cell lung cancer, prostate cancer and small-cell lung cancer.
18. The crystalline form M of compound A according to any one of claims 1 to 8, substantially as herein described with reference to any example thereof and with reference to the figures.
19. The pharmaceutical composition according to claim 9, substantially as herein described with reference to any example thereof and with reference to the figures.
20. The process according to any one of claims 10 to 15, substantially as herein described with reference to any example thereof and with reference to the figures.
21. The use according to claim 16 or claim 17, substantially as herein described with reference to any example thereof and with reference to the figures.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP18306634 | 2018-12-06 | ||
| PCT/EP2019/083773 WO2020115183A1 (en) | 2018-12-06 | 2019-12-05 | New crystalline forms of a mcl-1 inhibitor, a process for their preparation and pharmaceutical compositions containing them. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NZ776907A NZ776907A (en) | 2025-05-02 |
| NZ776907B2 true NZ776907B2 (en) | 2025-08-05 |
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