JP2021535218A - Dpp−iv阻害剤の血糖降下薬の新しい結晶形およびその調製方法 - Google Patents
Dpp−iv阻害剤の血糖降下薬の新しい結晶形およびその調製方法 Download PDFInfo
- Publication number
- JP2021535218A JP2021535218A JP2021536135A JP2021536135A JP2021535218A JP 2021535218 A JP2021535218 A JP 2021535218A JP 2021536135 A JP2021536135 A JP 2021536135A JP 2021536135 A JP2021536135 A JP 2021536135A JP 2021535218 A JP2021535218 A JP 2021535218A
- Authority
- JP
- Japan
- Prior art keywords
- crystalline form
- methyl
- crystal form
- 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.)
- Pending
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 239000003112 inhibitor Substances 0.000 title abstract description 4
- 239000003472 antidiabetic agent Substances 0.000 title abstract description 3
- 229940126904 hypoglycaemic agent Drugs 0.000 title abstract description 3
- 108010067722 Dipeptidyl Peptidase 4 Proteins 0.000 title abstract 2
- 102100025012 Dipeptidyl peptidase 4 Human genes 0.000 title abstract 2
- 238000000113 differential scanning calorimetry Methods 0.000 claims abstract description 35
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 34
- 238000001228 spectrum Methods 0.000 claims abstract description 26
- 125000000069 2-butynyl group Chemical group [H]C([H])([H])C#CC([H])([H])* 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 21
- 239000013078 crystal Substances 0.000 claims description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 239000007787 solid Substances 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 238000001816 cooling Methods 0.000 claims description 13
- 239000000463 material Substances 0.000 claims description 12
- 239000012046 mixed solvent Substances 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 11
- -1 4-methylquinazoline-2-yl Chemical group 0.000 claims description 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- JWEOEZZCZCCPJL-UHFFFAOYSA-N 4-methylquinazoline Chemical compound C1=CC=C2C(C)=NC=NC2=C1 JWEOEZZCZCCPJL-UHFFFAOYSA-N 0.000 claims description 7
- 238000001914 filtration Methods 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 239000002994 raw material Substances 0.000 claims description 4
- LTXREWYXXSTFRX-QGZVFWFLSA-N Linagliptin Chemical compound N=1C=2N(C)C(=O)N(CC=3N=C4C=CC=CC4=C(C)N=3)C(=O)C=2N(CC#CC)C=1N1CCC[C@@H](N)C1 LTXREWYXXSTFRX-QGZVFWFLSA-N 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims 1
- 230000008901 benefit Effects 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 238000010521 absorption reaction Methods 0.000 abstract 1
- 238000002411 thermogravimetry Methods 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 description 3
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- ZZKSBAFUNLAQGV-UHFFFAOYSA-N 1-[(4-methylquinazolin-2-yl)methyl]purine-2,6-dione Chemical compound C1=CC=C2C(C)=NC(CN3C(C4=NC=NC4=NC3=O)=O)=NC2=C1 ZZKSBAFUNLAQGV-UHFFFAOYSA-N 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 210000000941 bile Anatomy 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 229940090124 dipeptidyl peptidase 4 (dpp-4) inhibitors for blood glucose lowering Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- BCVXHSPFUWZLGQ-UHFFFAOYSA-N mecn acetonitrile Chemical compound CC#N.CC#N BCVXHSPFUWZLGQ-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
-
- 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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201810987434.3 | 2018-08-28 | ||
CN201810987434.3A CN109111443A (zh) | 2018-08-28 | 2018-08-28 | Dpp-iv抑制剂类降糖药的新晶型及其制备方法 |
PCT/CN2019/101198 WO2020042939A1 (zh) | 2018-08-28 | 2019-08-16 | Dpp-iv抑制剂类降糖药的新晶型及其制备方法 |
Publications (1)
Publication Number | Publication Date |
---|---|
JP2021535218A true JP2021535218A (ja) | 2021-12-16 |
Family
ID=64861326
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2021536135A Pending JP2021535218A (ja) | 2018-08-28 | 2019-08-16 | Dpp−iv阻害剤の血糖降下薬の新しい結晶形およびその調製方法 |
Country Status (3)
Country | Link |
---|---|
JP (1) | JP2021535218A (zh) |
CN (1) | CN109111443A (zh) |
WO (1) | WO2020042939A1 (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN110305131B (zh) * | 2019-07-03 | 2021-12-31 | 山东百诺医药股份有限公司 | 利格列汀新晶型及其制备方法 |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009535375A (ja) * | 2006-05-04 | 2009-10-01 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 多形体 |
WO2013074817A1 (en) * | 2011-11-16 | 2013-05-23 | Assia Chemical Industries Ltd. | Solid state forms of linagliptin |
WO2013098775A1 (en) * | 2011-12-28 | 2013-07-04 | Dr. Reddy's Laboratories Limited | Improved process for preparation of pure linagliptin |
WO2013128379A2 (en) * | 2012-02-27 | 2013-09-06 | Dr. Reddy's Laboratories Limited | Crystalline polymorphic forms of linagliptin |
CN105272982A (zh) * | 2015-11-23 | 2016-01-27 | 齐鲁制药有限公司 | 利格列汀新晶型及其制备方法 |
CN106146498A (zh) * | 2015-03-27 | 2016-11-23 | 天津汉瑞药业有限公司 | 一种新的利格列汀化合物 |
CN107043376A (zh) * | 2017-05-15 | 2017-08-15 | 珠海联邦制药股份有限公司 | 一种利格列汀新晶型及其制备方法 |
CN108017638A (zh) * | 2016-10-31 | 2018-05-11 | 江苏艾立康药业股份有限公司 | 一种利格列汀晶型的制备方法 |
JP2018177769A (ja) * | 2017-04-07 | 2018-11-15 | イルドン ファーマシューティカル カンパニー リミテッド | 1−[(4−メチル−キナゾリン−2−イル)メチル]−3−メチル−7−(2−ブチン−1−イル)−8−(3−(r)−アミノ−ピペリジン−1−イル)−キサンチンの新規結晶形及びその製造方法 |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PL2781637T3 (pl) * | 2012-11-30 | 2024-05-20 | Lg Energy Solution, Ltd. | Włóknina utworzona z włókna powlekanego organicznym polimerowym związkiem wiążącym, urządzenie elektrochemiczne obejmujące włókninię oraz sposób wytwarzania włókniny |
KR102442536B1 (ko) * | 2015-09-17 | 2022-09-13 | 한미정밀화학주식회사 | 리나글립틴 결정형 및 이의 제조방법 |
CN107987080A (zh) * | 2016-10-26 | 2018-05-04 | 上海奥博生物医药技术有限公司 | 一种利拉利汀晶型a的制备方法 |
-
2018
- 2018-08-28 CN CN201810987434.3A patent/CN109111443A/zh active Pending
-
2019
- 2019-08-16 JP JP2021536135A patent/JP2021535218A/ja active Pending
- 2019-08-16 WO PCT/CN2019/101198 patent/WO2020042939A1/zh active Application Filing
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2009535375A (ja) * | 2006-05-04 | 2009-10-01 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 多形体 |
WO2013074817A1 (en) * | 2011-11-16 | 2013-05-23 | Assia Chemical Industries Ltd. | Solid state forms of linagliptin |
WO2013098775A1 (en) * | 2011-12-28 | 2013-07-04 | Dr. Reddy's Laboratories Limited | Improved process for preparation of pure linagliptin |
WO2013128379A2 (en) * | 2012-02-27 | 2013-09-06 | Dr. Reddy's Laboratories Limited | Crystalline polymorphic forms of linagliptin |
CN106146498A (zh) * | 2015-03-27 | 2016-11-23 | 天津汉瑞药业有限公司 | 一种新的利格列汀化合物 |
CN105272982A (zh) * | 2015-11-23 | 2016-01-27 | 齐鲁制药有限公司 | 利格列汀新晶型及其制备方法 |
CN108017638A (zh) * | 2016-10-31 | 2018-05-11 | 江苏艾立康药业股份有限公司 | 一种利格列汀晶型的制备方法 |
JP2018177769A (ja) * | 2017-04-07 | 2018-11-15 | イルドン ファーマシューティカル カンパニー リミテッド | 1−[(4−メチル−キナゾリン−2−イル)メチル]−3−メチル−7−(2−ブチン−1−イル)−8−(3−(r)−アミノ−ピペリジン−1−イル)−キサンチンの新規結晶形及びその製造方法 |
CN107043376A (zh) * | 2017-05-15 | 2017-08-15 | 珠海联邦制药股份有限公司 | 一种利格列汀新晶型及其制备方法 |
Non-Patent Citations (8)
Title |
---|
大島寛: "結晶多形・擬多形の析出挙動と制御", PHARM STAGE, vol. 6, no. 10, JPN6011001457, 15 January 2007 (2007-01-15), pages 48 - 53, ISSN: 0004941694 * |
実験化学講座(続)2 分離と精製, JPN6012022299, 25 January 1967 (1967-01-25), JP, pages 159 - 178, ISSN: 0004941699 * |
山野光久: "医薬品のプロセス研究における結晶多形現象への取り組み", 有機合成化学協会誌, vol. 65, no. 9, JPN6010003277, 1 September 2007 (2007-09-01), pages 907 - 69, ISSN: 0004941696 * |
新・薬剤学総論(改訂第3版), vol. 株式会社南江堂, JPN6012025458, 10 April 1987 (1987-04-10), pages 111, ISSN: 0004941693 * |
新製剤学, JPN6012022297, 25 April 1984 (1984-04-25), pages 102 - 103, ISSN: 0004941692 * |
第十六改正 日本薬局方, JPN6014035187, 2011, pages 64 - 68, ISSN: 0004941698 * |
芦澤一英 他, 医薬品の多形現象と晶析の科学, JPN6018037400, 20 September 2002 (2002-09-20), JP, pages 3 - 16, ISSN: 0004941697 * |
高田則幸: "創薬段階における原薬Formスクリーニングと選択", PHARM STAGE, vol. 6, no. 10, JPN6009053755, 15 January 2007 (2007-01-15), pages 20 - 25, ISSN: 0004941695 * |
Also Published As
Publication number | Publication date |
---|---|
WO2020042939A1 (zh) | 2020-03-05 |
CN109111443A (zh) | 2019-01-01 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU2018234814B2 (en) | Crystal forms of amino lipids | |
US8093387B2 (en) | Process of making crystalline type II aripiprazole | |
US7902198B2 (en) | Crystalline aripiprazole solvates | |
JP5285914B2 (ja) | 有機化合物 | |
AU2012380672B2 (en) | Process for preparing crystalline Sorafenib tosylate | |
KR20150036336A (ko) | 타이로신 키나제 억제제 다이말리에이트의 결정형 아이 및 그의 제조 방법 | |
KR20180113822A (ko) | 1-[(4-메틸-퀴나졸린-2-일)메틸]-3-메틸-7-(2-부틴-1-일)-8-(3-(r)-아미노-피페리딘-1-일)-크산틴의 신규한 결정형 및 그의 제조방법 | |
WO2016150283A1 (zh) | 2-异丙氧基-5-甲基-4-(4-哌啶基)苯胺二盐酸盐的水合物、其制备方法及用途 | |
JP2021535218A (ja) | Dpp−iv阻害剤の血糖降下薬の新しい結晶形およびその調製方法 | |
WO2021075494A1 (ja) | センタナファジンの製造方法 | |
GB2550138A (en) | Process for preparing boscalid | |
EP1858855B2 (en) | Process of making crystalline type ii aripiprazole | |
CN110526897B (zh) | 制备吡虫啉多晶型的方法 | |
WO2017008772A1 (en) | Crystalline forms of (3r)-3-cyclopentyl-3-[4-(7h-pyrrolo[2,3-d]pyrimidin-4-yl)pyrazol-1-yl]propanenitrile salts and preparation thereof | |
JP2016175938A (ja) | エピルビシン塩酸塩の結晶化 | |
AU751561B2 (en) | Novel polymorphic forms of cipamfylline | |
CA3130247A1 (en) | Fgfr inhibitor compound in solid form and preparation method therefor | |
WO2014173377A2 (en) | New crystalline forms of apixaban and a method of their preparation | |
CN108718526B (zh) | 尼达尼布盐的结晶变态和其制备方法 | |
AU2007248282B2 (en) | Crystalline (3-cyano-1H-indol-7-yl)-[4-(4-fluorophenethyl)piperazin-1-yl]methanone phosphate | |
NZ630279B2 (en) | Process for preparing crystalline sorafenib tosylate |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20210423 |
|
A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20220413 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20220520 |
|
A02 | Decision of refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A02 Effective date: 20221212 |