JPWO2019206336A5 - - Google Patents
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- Publication number
- JPWO2019206336A5 JPWO2019206336A5 JP2021508055A JP2021508055A JPWO2019206336A5 JP WO2019206336 A5 JPWO2019206336 A5 JP WO2019206336A5 JP 2021508055 A JP2021508055 A JP 2021508055A JP 2021508055 A JP2021508055 A JP 2021508055A JP WO2019206336 A5 JPWO2019206336 A5 JP WO2019206336A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- crystal
- pattern shown
- 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
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- 229940125904 compound 1 Drugs 0.000 claims description 10
- 239000013078 crystal Substances 0.000 claims description 8
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 7
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- 238000001757 thermogravimetry curve Methods 0.000 claims 1
- 230000004580 weight loss Effects 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 238000011729 BALB/c nude mouse Methods 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 230000003285 pharmacodynamic effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- GRZHHTYDZVRPIC-UHFFFAOYSA-N (benzyloxy)acetic acid Chemical compound OC(=O)COCC1=CC=CC=C1 GRZHHTYDZVRPIC-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810399876.6 | 2018-04-28 | ||
| CN201810399876 | 2018-04-28 | ||
| PCT/CN2019/084822 WO2019206336A1 (zh) | 2018-04-28 | 2019-04-28 | 一种三唑并嘧啶类化合物的晶型、盐型及其制备方法 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2021522335A JP2021522335A (ja) | 2021-08-30 |
| JPWO2019206336A5 true JPWO2019206336A5 (zh) | 2022-05-06 |
| JP7406691B2 JP7406691B2 (ja) | 2023-12-28 |
Family
ID=68294924
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021508055A Active JP7406691B2 (ja) | 2018-04-28 | 2019-04-28 | トリアゾロピリミジン系化合物の結晶形、塩のタイプおよびその調製方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US11649239B2 (zh) |
| EP (1) | EP3766884B1 (zh) |
| JP (1) | JP7406691B2 (zh) |
| CN (1) | CN112105617B (zh) |
| DK (1) | DK3766884T3 (zh) |
| ES (1) | ES2908424T3 (zh) |
| PL (1) | PL3766884T3 (zh) |
| PT (1) | PT3766884T (zh) |
| WO (1) | WO2019206336A1 (zh) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2019206336A1 (zh) * | 2018-04-28 | 2019-10-31 | 南京明德新药研发有限公司 | 一种三唑并嘧啶类化合物的晶型、盐型及其制备方法 |
| TWI820209B (zh) | 2018-09-12 | 2023-11-01 | 大陸商迪哲（江蘇）醫藥股份有限公司 | 三唑并－嘧啶化合物及其用途 |
| WO2020106560A1 (en) * | 2018-11-20 | 2020-05-28 | Merck Sharp & Dohme Corp. | Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use |
| MX2022002219A (es) * | 2019-08-26 | 2022-06-14 | Incyte Corp | Triazolopirimidinas como inhibidores de a2a/a2b. |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69820866T2 (de) | 1997-03-24 | 2004-12-30 | Kyowa Hakko Kogyo Co., Ltd. | [1,2,4]TRIAZOLO[1,5-c]PYRIMIDIN-DERIVATE |
| PE20030739A1 (es) | 2001-11-30 | 2003-08-28 | Schering Corp | Antagonistas del receptor de adenosina a2a |
| CA2500228A1 (en) | 2002-09-24 | 2004-04-08 | Kyowa Hakko Kogyo Co., Ltd. | [1,2,4]-triazolo[1,5-c]pyrimidine derivative |
| PL3611174T3 (pl) | 2017-04-07 | 2022-08-08 | Medshine Discovery Inc. | Pochodne [1,2,4]triazolo[1,5-c]pirymidyny jako inhibitor receptora a2a |
| WO2019206336A1 (zh) * | 2018-04-28 | 2019-10-31 | 南京明德新药研发有限公司 | 一种三唑并嘧啶类化合物的晶型、盐型及其制备方法 |
-
2019
- 2019-04-28 WO PCT/CN2019/084822 patent/WO2019206336A1/zh unknown
- 2019-04-28 JP JP2021508055A patent/JP7406691B2/ja active Active
- 2019-04-28 CN CN201980023228.3A patent/CN112105617B/zh active Active
- 2019-04-28 PL PL19793622.2T patent/PL3766884T3/pl unknown
- 2019-04-28 EP EP19793622.2A patent/EP3766884B1/en active Active
- 2019-04-28 PT PT197936222T patent/PT3766884T/pt unknown
- 2019-04-28 DK DK19793622.2T patent/DK3766884T3/da active
- 2019-04-28 US US17/044,127 patent/US11649239B2/en active Active
- 2019-04-28 ES ES19793622T patent/ES2908424T3/es active Active
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