CN106661040B - 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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- CN106661040B CN106661040B CN201580026821.5A CN201580026821A CN106661040B CN 106661040 B CN106661040 B CN 106661040B CN 201580026821 A CN201580026821 A CN 201580026821A CN 106661040 B CN106661040 B CN 106661040B
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- 238000002425 crystallisation Methods 0.000 title claims abstract description 60
- 230000008025 crystallization Effects 0.000 title claims abstract description 60
- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title abstract description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title abstract description 8
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 title abstract description 5
- 239000002798 polar solvent Substances 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 15
- 150000001875 compounds Chemical class 0.000 claims description 53
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 21
- 239000013078 crystal Substances 0.000 claims description 17
- 238000001228 spectrum Methods 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Natural products CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000001816 cooling Methods 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 11
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 11
- 239000012043 crude product Substances 0.000 claims description 9
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- 235000019441 ethanol Nutrition 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
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- 206010028980 Neoplasm Diseases 0.000 claims description 4
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- 206010061218 Inflammation Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 230000004054 inflammatory process Effects 0.000 claims description 3
- 239000000010 aprotic solvent Substances 0.000 claims 1
- 125000005909 ethyl alcohol group Chemical group 0.000 claims 1
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- 229910052740 iodine Inorganic materials 0.000 abstract description 2
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- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
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- 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
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- 230000002062 proliferating effect Effects 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000013112 stability test Methods 0.000 description 2
- -1 2- vinyloxyethoxy Chemical group 0.000 description 1
- 208000023275 Autoimmune disease Diseases 0.000 description 1
- 206010008190 Cerebrovascular accident Diseases 0.000 description 1
- 102100021202 Desmocollin-1 Human genes 0.000 description 1
- 101000968043 Homo sapiens Desmocollin-1 Proteins 0.000 description 1
- 101000880960 Homo sapiens Desmocollin-3 Proteins 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
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
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- 239000012895 dilution Substances 0.000 description 1
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- 238000010828 elution Methods 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
- 239000005457 ice water Substances 0.000 description 1
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- 239000012535 impurity Substances 0.000 description 1
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- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 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
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000010512 thermal transition Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
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
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 (17)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
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 |
Publications (2)
Publication Number | Publication Date |
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CN106661040A CN106661040A (zh) | 2017-05-10 |
CN106661040B true CN106661040B (zh) | 2019-04-26 |
Family
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CN201410383541.7A Active 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 |
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 |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
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CN201410383541.7A Active 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 |
Country Status (8)
Country | Link |
---|---|
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) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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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 |
EP3305292B1 (en) * | 2015-05-28 | 2022-09-14 | 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 |
---|---|---|---|---|
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 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 AU AU2015299546A patent/AU2015299546B2/en active Active
- 2015-08-05 EP EP15830563.1A patent/EP3178821B1/en active Active
- 2015-08-05 JP JP2017505846A patent/JP6929769B2/ja active Active
- 2015-08-05 US US15/329,197 patent/US10023582B2/en active Active
- 2015-08-05 KR KR1020177006090A patent/KR20170032476A/ko not_active Application Discontinuation
- 2015-08-05 CN CN201580026821.5A patent/CN106661040B/zh active Active
- 2015-08-05 WO PCT/CN2015/086118 patent/WO2016019867A1/zh active Application Filing
- 2015-08-05 CA CA2956404A patent/CA2956404A1/en not_active Abandoned
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 (1)
Title |
---|
药物的结晶状态及其在药学上的应用(一);贺全山;《药学情报通讯》;19861231(第1期);第63-66页,第66页左栏第4段 |
Also Published As
Publication number | Publication date |
---|---|
EP3178821A1 (en) | 2017-06-14 |
CN105315291A (zh) | 2016-02-10 |
US20170217979A1 (en) | 2017-08-03 |
AU2015299546A1 (en) | 2017-03-16 |
EP3178821A4 (en) | 2018-01-03 |
CA2956404A1 (en) | 2016-02-11 |
AU2015299546B2 (en) | 2019-07-11 |
EP3178821B1 (en) | 2020-05-06 |
CN106661040A (zh) | 2017-05-10 |
KR20170032476A (ko) | 2017-03-22 |
WO2016019867A1 (zh) | 2016-02-11 |
CN105315291B (zh) | 2019-02-01 |
JP2017523210A (ja) | 2017-08-17 |
JP6929769B2 (ja) | 2021-09-01 |
US10023582B2 (en) | 2018-07-17 |
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Effective date of registration: 20190524 Address after: No. 369, Yuzhou South Road, Lianyungang, Jiangsu Province Co-patentee after: Capital Pharmaceutical Holdings (Beijing) Co., Ltd. Patentee after: Chia Tai Tianqing Pharmaceutical Group Co., Ltd. Address before: 222062 Yuzhou South Road, Haizhou District, Lianyungang, Jiangsu 369 Co-patentee before: Beijing Centaurus Biopharma Technology Co., Ltd. Patentee before: Chia Tai Tianqing Pharmaceutical Group Co., Ltd. |
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Address after: No. 369, Yuzhou South Road, Lianyungang, Jiangsu Province Patentee after: CHIA TAI TIANQING PHARMACEUTICAL GROUP Co.,Ltd. Patentee after: Capital Pharmaceutical Holdings (Beijing) Co.,Ltd. Address before: No. 369, Yuzhou South Road, Lianyungang, Jiangsu Province Patentee before: CHIA TAI TIANQING PHARMACEUTICAL GROUP Co.,Ltd. Patentee before: Shouyao holding (Beijing) Co.,Ltd. |