JP2015536993A5 - - Google Patents
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- Publication number
- JP2015536993A5 JP2015536993A5 JP2015541965A JP2015541965A JP2015536993A5 JP 2015536993 A5 JP2015536993 A5 JP 2015536993A5 JP 2015541965 A JP2015541965 A JP 2015541965A JP 2015541965 A JP2015541965 A JP 2015541965A JP 2015536993 A5 JP2015536993 A5 JP 2015536993A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- methylpyridin
- oxy
- thiadiazol
- ethane
- 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
- -1 2,2-dimethyl-1,3-dioxolan-4-yl Chemical group 0.000 claims description 34
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 14
- PCOMIRCNMMNOAP-CQSZACIVSA-N (1s)-1-[5-[[3-(2-methylpyridin-3-yl)oxy-5-pyridin-2-ylsulfanylpyridin-2-yl]amino]-1,2,4-thiadiazol-3-yl]ethane-1,2-diol Chemical compound CC1=NC=CC=C1OC1=CC(SC=2N=CC=CC=2)=CN=C1NC1=NC([C@H](O)CO)=NS1 PCOMIRCNMMNOAP-CQSZACIVSA-N 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 239000002245 particle Substances 0.000 claims description 13
- 239000003929 acidic solution Substances 0.000 claims description 12
- 235000019441 ethanol Nutrition 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- 150000004682 monohydrates Chemical class 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000002585 base Substances 0.000 claims description 4
- 206010012601 diabetes mellitus Diseases 0.000 claims description 4
- OASOQJKCZXXDMI-UHFFFAOYSA-N ethane-1,2-diol;hydrochloride Chemical compound Cl.OCCO OASOQJKCZXXDMI-UHFFFAOYSA-N 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims description 4
- DUXHPMVXLVRKIJ-PFEQFJNWSA-N (1s)-1-[5-[[3-(2-methylpyridin-3-yl)oxy-5-pyridin-2-ylsulfanylpyridin-2-yl]amino]-1,2,4-thiadiazol-3-yl]ethane-1,2-diol;hydrate Chemical compound O.CC1=NC=CC=C1OC1=CC(SC=2N=CC=CC=2)=CN=C1NC1=NC([C@H](O)CO)=NS1 DUXHPMVXLVRKIJ-PFEQFJNWSA-N 0.000 claims description 2
- CIYVDXOYLGRSIZ-PFEQFJNWSA-N (1s)-1-[5-[[3-(2-methylpyridin-3-yl)oxy-5-pyridin-2-ylsulfanylpyridin-2-yl]amino]-1,2,4-thiadiazol-3-yl]ethane-1,2-diol;hydrochloride Chemical compound Cl.CC1=NC=CC=C1OC1=CC(SC=2N=CC=CC=2)=CN=C1NC1=NC([C@H](O)CO)=NS1 CIYVDXOYLGRSIZ-PFEQFJNWSA-N 0.000 claims description 2
- NULTWZGZTCYLAO-UHFFFAOYSA-N 2-chloro-3-(2-methylpyridin-3-yl)oxy-5-pyridin-2-ylsulfanylpyridine Chemical compound CC1=NC=CC=C1OC1=CC(SC=2N=CC=CC=2)=CN=C1Cl NULTWZGZTCYLAO-UHFFFAOYSA-N 0.000 claims description 2
- MYTYUHFMAZZKEA-UHFFFAOYSA-N 3-(2-methylpyridin-3-yl)oxy-1-oxido-5-pyridin-2-ylsulfanylpyridin-1-ium Chemical compound CC1=NC=CC=C1OC1=CC(SC=2N=CC=CC=2)=C[N+]([O-])=C1 MYTYUHFMAZZKEA-UHFFFAOYSA-N 0.000 claims description 2
- FWNGAYSESJABMA-UHFFFAOYSA-N 3-(2-methylpyridin-3-yl)oxy-5-pyridin-2-ylsulfanylpyridin-2-amine Chemical compound CC1=NC=CC=C1OC1=CC(SC=2N=CC=CC=2)=CN=C1N FWNGAYSESJABMA-UHFFFAOYSA-N 0.000 claims description 2
- SPKQOSUAPMJTSM-SSDOTTSWSA-N 3-[(3s)-1,4-dioxaspiro[4.5]decan-3-yl]-1,2,4-thiadiazol-5-amine Chemical compound S1C(N)=NC([C@@H]2OC3(CCCCC3)OC2)=N1 SPKQOSUAPMJTSM-SSDOTTSWSA-N 0.000 claims description 2
- CXPLZGWYTGUTHV-GOSISDBHSA-N 3-[(4s)-2,2-dimethyl-1,3-dioxolan-4-yl]-n-[3-(2-methylpyridin-3-yl)oxy-5-pyridin-2-ylsulfanylpyridin-2-yl]-1,2,4-thiadiazol-5-amine Chemical compound CC1=NC=CC=C1OC1=CC(SC=2N=CC=CC=2)=CN=C1NC1=NC([C@@H]2OC(C)(C)OC2)=NS1 CXPLZGWYTGUTHV-GOSISDBHSA-N 0.000 claims description 2
- IIQWOHRWKXHMPK-UHFFFAOYSA-N 3-[3-(2-methylpyridin-3-yl)oxy-5-pyridin-2-ylsulfanylpyridin-2-yl]-1,2,4-thiadiazol-5-amine Chemical compound CC1=NC=CC=C1OC=1C(=NC=C(C=1)SC1=NC=CC=C1)C1=NSC(=N1)N IIQWOHRWKXHMPK-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 2
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- UFWLOBHANVUABF-UHFFFAOYSA-N ethane-1,2-diol hydrate Chemical compound O.OCCO.OCCO UFWLOBHANVUABF-UHFFFAOYSA-N 0.000 claims description 2
- 238000010899 nucleation Methods 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 235000011056 potassium acetate Nutrition 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000004515 1,2,4-thiadiazol-3-yl group Chemical group S1N=C(N=C1)* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261724497P | 2012-11-09 | 2012-11-09 | |
| US61/724,497 | 2012-11-09 | ||
| PCT/US2013/069331 WO2014074940A1 (en) | 2012-11-09 | 2013-11-08 | Crystalline forms of (1s)-1-[5-({3-[(2-methylpyridin-3-yl)oxy]-5-(pyridin-2-ylsulfanyl)pyridin-2-yl}amino)-1,2,4-thiadiazol-3-yl]ethane-1,2-diol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2015536993A JP2015536993A (ja) | 2015-12-24 |
| JP2015536993A5 true JP2015536993A5 (enExample) | 2016-12-08 |
Family
ID=49753457
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015541965A Pending JP2015536993A (ja) | 2012-11-09 | 2013-11-08 | （１ｓ）−１−［５−（｛３−［（２−メチルピリジン−３−イル）オキシ］−５−（ピリジン−２−イルスルファニル）ピリジン−２−イル｝アミノ）−１，２，４−チアジアゾール−３−イル］エタン−１，２−ジオールの結晶形態 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20150299182A1 (enExample) |
| EP (1) | EP2917213A1 (enExample) |
| JP (1) | JP2015536993A (enExample) |
| CN (1) | CN105164123A (enExample) |
| CA (1) | CA2890852A1 (enExample) |
| WO (1) | WO2014074940A1 (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105601586B (zh) * | 2016-01-16 | 2017-10-20 | 陈洪国 | 一种治疗乙肝的药物组合物 |
| CN111220614B (zh) * | 2018-11-27 | 2023-05-09 | 宝山钢铁股份有限公司 | 一种快速评估钢水质量的方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6096767A (en) * | 1999-01-22 | 2000-08-01 | The University Of Toledo | Muscarinic receptor agonists |
| SI2013204T1 (sl) * | 2006-03-24 | 2015-06-30 | Array Biopharma, Inc. | Analogi 2-aminopriridina kot aktivatorji glukokinaze |
| SI2209778T1 (sl) * | 2007-09-21 | 2012-12-31 | Array Biopharma, Inc. | Piridin-2-il-amino-I, 2,4-tiadiazol derivati kot aktivatorji glukokinaze za zdravljenje sladkorne bolezni |
-
2013
- 2013-11-08 CN CN201380065864.5A patent/CN105164123A/zh active Pending
- 2013-11-08 EP EP13802758.6A patent/EP2917213A1/en not_active Withdrawn
- 2013-11-08 US US14/441,133 patent/US20150299182A1/en not_active Abandoned
- 2013-11-08 CA CA2890852A patent/CA2890852A1/en not_active Abandoned
- 2013-11-08 WO PCT/US2013/069331 patent/WO2014074940A1/en not_active Ceased
- 2013-11-08 JP JP2015541965A patent/JP2015536993A/ja active Pending
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