CN106661040A - 一种6‑芳基氨基吡啶酮甲酰胺化合物的结晶及其制备方法 - Google Patents
一种6‑芳基氨基吡啶酮甲酰胺化合物的结晶及其制备方法 Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 51
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- 238000002425 crystallisation Methods 0.000 claims abstract description 51
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 230000008025 crystallization Effects 0.000 claims description 50
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 238000001228 spectrum Methods 0.000 claims description 14
- 238000001816 cooling Methods 0.000 claims description 12
- 239000002798 polar solvent Substances 0.000 claims description 11
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 201000010099 disease Diseases 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- 239000012043 crude product Substances 0.000 claims description 6
- 239000012046 mixed solvent Substances 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 238000003860 storage Methods 0.000 abstract description 2
- 238000009776 industrial production Methods 0.000 abstract 1
- 239000003880 polar aprotic solvent Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 9
- 238000005352 clarification Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- FWQHRZXEQNUCSY-UHFFFAOYSA-N tert-butyl N-[2-(ethoxycarbonylamino)-5-[(4-fluorophenyl)methyl-prop-2-ynylamino]phenyl]carbamate Chemical compound CCOC(=O)NC1=C(C=C(C=C1)N(CC#C)CC2=CC=C(C=C2)F)NC(=O)OC(C)(C)C FWQHRZXEQNUCSY-UHFFFAOYSA-N 0.000 description 7
- 238000010792 warming Methods 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 230000002062 proliferating effect Effects 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 201000011510 cancer Diseases 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 206010008190 Cerebrovascular accident Diseases 0.000 description 1
- 229940124647 MEK inhibitor Drugs 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- -1 anilino- Chemical class 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000010812 external standard method Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
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- 239000012535 impurity Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
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- 238000011835 investigation Methods 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
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- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000013094 purity test Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4355—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having oxygen as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
编号 | 衍射峰(°) | 相对强度(%) |
1 | 7.86 | 100 |
2 | 9.32 | 33 |
3 | 13.25 | 41 |
4 | 15.06 | 42 |
5 | 17.89 | 18 |
6 | 19.09 | 67 |
7 | 20.73 | 27 |
8 | 21.80 | 44 |
9 | 22.46 | 37 |
10 | 22.81 | 39 |
11 | 23.87 | 95 |
12 | 24.55 | 21 |
13 | 26.00 | 65 |
14 | 27.29 | 19 |
15 | 28.12 | 43 |
16 | 28.59 | 40 |
17 | 29.32 | 18 |
18 | 30.15 | 20 |
Claims (10)
- 一种式(I)化合物的结晶,其特征是X-射线粉末衍射光谱用2°值表示在7.86°、19.09°、21.80°、23.87°、26.00°、28.12°处有衍射峰。
- 权利要求1所述的结晶,其X-射线粉末衍射光谱用2°值表示在7.86°、9.32°、13.25°、15.06°、19.09°、21.80°、22.46°、22.81°、23.87°、26.00°、28.12°、28.59°处有衍射峰。
- 权利要求2所述的结晶,其X-射线粉末衍射光谱用2°值表示在7.86°、9.32°、13.25°、15.06°、17.89°、19.09°、20.73°、21.80°、22.46°、22.81°、23.87°、24.55°、26.00°、27.29°、28.12°、28.59°、29.32°、30.15°处有衍射峰。
- 一种结晶组合物,其中权利要求1~3任一项所述的式(I)化合物的结晶占结晶组合物重量50%以上,较好是80%以上,更好是90%以上,最好是95%以上。
- 一种药物组合物,其中包含治疗有效量的权利要求1~4任一项所述的式(I)化合物的结晶或结晶组合物。
- 权利要求1~5任一项所述的式(I)化合物的结晶、结晶组合物或药物组合物在制备用于治疗或预防MEK介导的病症或疾病的药物组合物中的应用。
- 一种制备式(I)化合物的结晶或结晶组合物的方法,其包括如下步骤:将式(I)化合物的粗品溶于温度为80℃~120℃的非质子极性溶剂中,降温,加入第二种溶剂,析晶,过滤,干燥。
- 权利要求7所述的方法,其中非质子极性溶剂选自DMF、DMSO或上述溶剂的混合溶剂,优选DMSO。
- 权利要求7所述的方法,其中第二种溶剂选自水、醇类或上述溶剂的混合溶剂,优选水、甲醇、乙醇、正丙醇、异丙醇、正丁醇、异丁醇或上述溶剂两种以上的混合溶剂,进一步优选乙醇、水或上述两种溶剂的混合物。
- 权利要求7所述的方法,其中第二种溶剂与非质子极性溶剂的体积比为0.25∶1~5∶1,优选0.5∶1~3∶1,更进一步优选1∶1~2∶1。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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CN201410383541.7A CN105315291B (zh) | 2014-08-05 | 2014-08-05 | 一种6-芳基氨基吡啶酮甲酰胺化合物的结晶及其制备方法 |
CN2014103835417 | 2014-08-05 | ||
PCT/CN2015/086118 WO2016019867A1 (zh) | 2014-08-05 | 2015-08-05 | 一种6-芳基氨基吡啶酮甲酰胺化合物的结晶及其制备方法 |
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CN106661040A true CN106661040A (zh) | 2017-05-10 |
CN106661040B CN106661040B (zh) | 2019-04-26 |
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CN201580026821.5A Active CN106661040B (zh) | 2014-08-05 | 2015-08-05 | 一种6-芳基氨基吡啶酮甲酰胺化合物的结晶及其制备方法 |
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Country Status (8)
Country | Link |
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US (1) | US10023582B2 (zh) |
EP (1) | EP3178821B1 (zh) |
JP (1) | JP6929769B2 (zh) |
KR (1) | KR20170032476A (zh) |
CN (2) | CN105315291B (zh) |
AU (1) | AU2015299546B2 (zh) |
CA (1) | CA2956404A1 (zh) |
WO (1) | WO2016019867A1 (zh) |
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CN105315291B (zh) * | 2014-08-05 | 2019-02-01 | 正大天晴药业集团股份有限公司 | 一种6-芳基氨基吡啶酮甲酰胺化合物的结晶及其制备方法 |
US10350198B2 (en) | 2015-05-28 | 2019-07-16 | Chia Tai Tianqing Pharmaceutical Group Co., Ltd. | Pharmaceutical composition of MEK inhibitor and preparation method thereof |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US20120238599A1 (en) * | 2011-03-17 | 2012-09-20 | Chemizon, A Division Of Optomagic Co., Ltd. | Heterocyclic compounds as mek inhibitors |
CN105315291A (zh) * | 2014-08-05 | 2016-02-10 | 正大天晴药业集团股份有限公司 | 一种6-芳基氨基吡啶酮甲酰胺化合物的结晶及其制备方法 |
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CN102020651B (zh) * | 2010-11-02 | 2012-07-18 | 北京赛林泰医药技术有限公司 | 6-芳基氨基吡啶酮甲酰胺mek抑制剂 |
-
2014
- 2014-08-05 CN CN201410383541.7A patent/CN105315291B/zh active Active
-
2015
- 2015-08-05 WO PCT/CN2015/086118 patent/WO2016019867A1/zh active Application Filing
- 2015-08-05 CN CN201580026821.5A patent/CN106661040B/zh active Active
- 2015-08-05 US US15/329,197 patent/US10023582B2/en active Active
- 2015-08-05 JP JP2017505846A patent/JP6929769B2/ja active Active
- 2015-08-05 EP EP15830563.1A patent/EP3178821B1/en active Active
- 2015-08-05 KR KR1020177006090A patent/KR20170032476A/ko not_active Application Discontinuation
- 2015-08-05 CA CA2956404A patent/CA2956404A1/en not_active Abandoned
- 2015-08-05 AU AU2015299546A patent/AU2015299546B2/en active Active
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20120238599A1 (en) * | 2011-03-17 | 2012-09-20 | Chemizon, A Division Of Optomagic Co., Ltd. | Heterocyclic compounds as mek inhibitors |
CN105315291A (zh) * | 2014-08-05 | 2016-02-10 | 正大天晴药业集团股份有限公司 | 一种6-芳基氨基吡啶酮甲酰胺化合物的结晶及其制备方法 |
Non-Patent Citations (2)
Title |
---|
吕扬 等: "《晶型药物》", 31 October 2009, 人民卫生出版社 * |
贺全山: "药物的结晶状态及其在药学上的应用(一)", 《药学情报通讯》 * |
Also Published As
Publication number | Publication date |
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JP2017523210A (ja) | 2017-08-17 |
EP3178821B1 (en) | 2020-05-06 |
CN106661040B (zh) | 2019-04-26 |
WO2016019867A1 (zh) | 2016-02-11 |
EP3178821A1 (en) | 2017-06-14 |
CN105315291B (zh) | 2019-02-01 |
EP3178821A4 (en) | 2018-01-03 |
KR20170032476A (ko) | 2017-03-22 |
CN105315291A (zh) | 2016-02-10 |
AU2015299546B2 (en) | 2019-07-11 |
CA2956404A1 (en) | 2016-02-11 |
US20170217979A1 (en) | 2017-08-03 |
US10023582B2 (en) | 2018-07-17 |
AU2015299546A1 (en) | 2017-03-16 |
JP6929769B2 (ja) | 2021-09-01 |
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