CN110291071A - Sb-939的盐的晶型及其制备方法和用途 - Google Patents
Sb-939的盐的晶型及其制备方法和用途 Download PDFInfo
- Publication number
- CN110291071A CN110291071A CN201880011239.5A CN201880011239A CN110291071A CN 110291071 A CN110291071 A CN 110291071A CN 201880011239 A CN201880011239 A CN 201880011239A CN 110291071 A CN110291071 A CN 110291071A
- Authority
- CN
- China
- Prior art keywords
- crystal form
- solvent
- dihydrochloride
- ray powder
- powder diffraction
- 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.)
- Granted
Links
- 239000013078 crystal Substances 0.000 title claims abstract description 234
- 238000002360 preparation method Methods 0.000 title claims abstract description 40
- JHDKZFFAIZKUCU-ZRDIBKRKSA-N pracinostat Chemical compound ONC(=O)/C=C/C1=CC=C2N(CCN(CC)CC)C(CCCC)=NC2=C1 JHDKZFFAIZKUCU-ZRDIBKRKSA-N 0.000 title claims description 56
- 150000003839 salts Chemical class 0.000 title abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 25
- 229940079593 drug Drugs 0.000 claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 123
- 239000002904 solvent Substances 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 34
- 235000019441 ethanol Nutrition 0.000 claims description 26
- 150000001298 alcohols Chemical class 0.000 claims description 24
- 239000012296 anti-solvent Substances 0.000 claims description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 18
- 238000003756 stirring Methods 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- 150000002825 nitriles Chemical class 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 150000002576 ketones Chemical class 0.000 claims description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 11
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 8
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 7
- 239000012046 mixed solvent Substances 0.000 claims description 7
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical group CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 claims description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 6
- 229940043265 methyl isobutyl ketone Drugs 0.000 claims description 6
- 150000003462 sulfoxides Chemical class 0.000 claims description 6
- 229940011051 isopropyl acetate Drugs 0.000 claims description 5
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical group CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims description 3
- 206010060862 Prostate cancer Diseases 0.000 claims description 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical group CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 229940113088 dimethylacetamide Drugs 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000011287 therapeutic dose Methods 0.000 claims description 2
- 230000015556 catabolic process Effects 0.000 abstract description 2
- 238000006731 degradation reaction Methods 0.000 abstract description 2
- 238000009509 drug development Methods 0.000 abstract description 2
- 238000000227 grinding Methods 0.000 description 28
- 239000007787 solid Substances 0.000 description 21
- 238000000113 differential scanning calorimetry Methods 0.000 description 18
- 238000012360 testing method Methods 0.000 description 18
- 238000002411 thermogravimetry Methods 0.000 description 18
- 230000008859 change Effects 0.000 description 9
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 8
- 238000003860 storage Methods 0.000 description 8
- 238000001757 thermogravimetry curve Methods 0.000 description 8
- 239000002994 raw material Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 230000008569 process Effects 0.000 description 5
- 238000011160 research Methods 0.000 description 5
- 230000004584 weight gain Effects 0.000 description 5
- 235000019786 weight gain Nutrition 0.000 description 5
- 229910017488 Cu K Inorganic materials 0.000 description 4
- 229910017541 Cu-K Inorganic materials 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000008901 benefit Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- 208000030453 Drug-Related Side Effects and Adverse reaction Diseases 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000857 drug effect Effects 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000003908 quality control method Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- 206010061623 Adverse drug reaction Diseases 0.000 description 1
- 230000004543 DNA replication Effects 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 102000003964 Histone deacetylase Human genes 0.000 description 1
- 108090000353 Histone deacetylase Proteins 0.000 description 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 206010070863 Toxicity to various agents Diseases 0.000 description 1
- 108700025716 Tumor Suppressor Genes Proteins 0.000 description 1
- 102000044209 Tumor Suppressor Genes Human genes 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 210000000349 chromosome Anatomy 0.000 description 1
- 229940121657 clinical drug Drugs 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000017858 demethylation Effects 0.000 description 1
- 238000010520 demethylation reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000012362 drug development process Methods 0.000 description 1
- 238000009837 dry grinding Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000004049 epigenetic modification Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 229940121372 histone deacetylase inhibitor Drugs 0.000 description 1
- 239000003276 histone deacetylase inhibitor Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 229950003618 pracinostat Drugs 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 238000004445 quantitative analysis Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- -1 semisolid Substances 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000004441 surface measurement Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 210000004881 tumor cell Anatomy 0.000 description 1
Classifications
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
-
- 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
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- C07D235/08—Radicals containing only hydrogen and carbon atoms
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
本发明涉及化合物(I)的盐的晶型及其制备方法和用途。本发明提供的新晶型CS7、CS9、CS1和CS3的引湿性低、稳定性好、纯度高、不易发生降解、溶解度高且机械稳定性好。为含化合物(I)药物的制备提供了新的更好的选择，对于药物开发具有非常重要的意义。
Description
PCT国内申请，说明书已公开。
Claims (22)
- PCT国内申请，权利要求书已公开。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710112053 | 2017-02-28 | ||
| CN2017101120536 | 2017-02-28 | ||
| PCT/CN2018/076607 WO2018157741A1 (zh) | 2017-02-28 | 2018-02-13 | Sb-939的盐的晶型及其制备方法和用途 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110291071A true CN110291071A (zh) | 2019-09-27 |
| CN110291071B CN110291071B (zh) | 2022-04-26 |
Family
ID=63369756
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201880011239.5A Expired - Fee Related CN110291071B (zh) | 2017-02-28 | 2018-02-13 | Sb-939的盐的晶型及其制备方法和用途 |
Country Status (2)
| Country | Link |
|---|---|
| CN (1) | CN110291071B (zh) |
| WO (2) | WO2018157742A1 (zh) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20230159468A1 (en) | 2020-04-22 | 2023-05-25 | Macfarlan Smith Limited | Novel forms of pracinostat dihydrochloride |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101287712A (zh) * | 2005-09-08 | 2008-10-15 | S*Bio私人有限公司 | 杂环化合物 |
| WO2017192451A1 (en) * | 2016-05-02 | 2017-11-09 | Mei Pharma, Inc. | Polymorphic forms of 3-[2-butyl-1-(2-diethylamino-ehtyl)-1h-benzoimidazol-5-yl]-n-hydroxy-acrylamide and uses thereof |
-
2018
- 2018-02-13 CN CN201880011239.5A patent/CN110291071B/zh not_active Expired - Fee Related
- 2018-02-13 WO PCT/CN2018/076609 patent/WO2018157742A1/zh active Application Filing
- 2018-02-13 WO PCT/CN2018/076607 patent/WO2018157741A1/zh active Application Filing
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101287712A (zh) * | 2005-09-08 | 2008-10-15 | S*Bio私人有限公司 | 杂环化合物 |
| WO2017192451A1 (en) * | 2016-05-02 | 2017-11-09 | Mei Pharma, Inc. | Polymorphic forms of 3-[2-butyl-1-(2-diethylamino-ehtyl)-1h-benzoimidazol-5-yl]-n-hydroxy-acrylamide and uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2018157742A1 (zh) | 2018-09-07 |
| CN110291071B (zh) | 2022-04-26 |
| WO2018157741A1 (zh) | 2018-09-07 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US10414741B2 (en) | Amorphous vortioxetine and salts thereof | |
| CN110494423B (zh) | 乐伐替尼甲磺酸盐的新晶型及其制备方法 | |
| CN109219597A (zh) | 奥扎莫德的晶型、其盐酸盐的晶型及其制备方法 | |
| CN102459170B (zh) | 沙格列汀的结晶形式 | |
| KR20170137916A (ko) | 우라실 화합물의 신규 결정 | |
| CN110088088A (zh) | {[5-(3-氯苯基)-3-羟基吡啶-2-羰基]氨基}乙酸的新晶型及其制备方法 | |
| CN109641851A (zh) | 一种雄激素受体拮抗剂药物的晶型及其制备方法和用途 | |
| CN102086195A (zh) | 达沙替尼多晶型物及其制备方法和药用组合物 | |
| CN105732575A (zh) | 一种治疗前列腺癌的新型抗雄激素类药物的新晶型及其制备方法 | |
| CN110128356A (zh) | 一种吉非替尼与3-羟基苯甲酸共晶体 | |
| CN109195980A (zh) | 一种钠-葡萄糖协同转运蛋白抑制剂药物的新晶型及其制备方法和用途 | |
| US9884856B2 (en) | Crystal form of Dabrafenib mesylate and preparation method thereof | |
| CN110291071A (zh) | Sb-939的盐的晶型及其制备方法和用途 | |
| CN110312705A (zh) | Gft-505的晶型及其制备方法和用途 | |
| CN106565699B (zh) | 一种艾沙康唑硫酸盐晶体及其制备方法 | |
| CN104529919A (zh) | 2-(5-溴-4-(4-环丙基萘-1-基)-4h-1,2,4-三唑-3-基硫基)乙酸的共晶及其制备方法 | |
| CN110156793A (zh) | 瑞博西尼单琥珀酸盐新晶型及制备方法 | |
| CN109153677A (zh) | Plx3397的盐酸盐晶型及其制备方法和用途 | |
| Shiraki | Physical characterization of TRK-720 hydrate, the very late antigen-4 (VLA-4) inhibitor, as a solid form for inhalation: preparation of the hydrate by solvent exchange among its solvates and mechanistical considerations | |
| CN109476689A (zh) | 富马酸替诺福韦艾拉酚胺盐的新晶型、制备方法及其用途 | |
| CN106478598B (zh) | 一种凡德他尼水合物晶体及其制备方法 | |
| CN110036003A (zh) | Ap26113的新晶型及其制备方法 | |
| CN102030744A (zh) | 伊潘立酮晶体、其制备方法及药物组合物 | |
| CN105693699B (zh) | 托吡司他的晶型及其制备方法 | |
| CN105732642B (zh) | 一种cdk抑制剂和mek抑制剂的共晶及其制备方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20220426 |