JP2015517531A5 - - Google Patents
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- Publication number
- JP2015517531A5 JP2015517531A5 JP2015512873A JP2015512873A JP2015517531A5 JP 2015517531 A5 JP2015517531 A5 JP 2015517531A5 JP 2015512873 A JP2015512873 A JP 2015512873A JP 2015512873 A JP2015512873 A JP 2015512873A JP 2015517531 A5 JP2015517531 A5 JP 2015517531A5
- Authority
- JP
- Japan
- Prior art keywords
- item
- alkyl
- optionally substituted
- dioxolan
- hydroxy
- 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
Links
- 238000000034 method Methods 0.000 claims description 45
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 13
- -1 1,3-dioxolan-4-yl (hydroxy) methanesulfonate Chemical class 0.000 claims description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 10
- 241000872931 Myoporum sandwicense Species 0.000 claims description 8
- 238000007248 oxidative elimination reaction Methods 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 238000010276 construction Methods 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- YKGMKSIHIVVYKY-UHFFFAOYSA-N dabrafenib mesylate Chemical compound CS(O)(=O)=O.S1C(C(C)(C)C)=NC(C=2C(=C(NS(=O)(=O)C=3C(=CC=CC=3F)F)C=CC=2)F)=C1C1=CC=NC(N)=N1 YKGMKSIHIVVYKY-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 3
- 238000005660 chlorination reaction Methods 0.000 claims description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 3
- ODYBCPSCYHAGHA-ZYUZMQFOSA-N (1s,2s)-1,2-bis[(4r)-2,2-dimethyl-1,3-dioxolan-4-yl]ethane-1,2-diol Chemical compound O1C(C)(C)OC[C@@H]1[C@@H](O)[C@H](O)[C@@H]1OC(C)(C)OC1 ODYBCPSCYHAGHA-ZYUZMQFOSA-N 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims description 2
- UAUDPSIEUSNACO-UHFFFAOYSA-N methanesulfonoperoxoic acid;sodium Chemical compound [Na].CS(=O)(=O)OO UAUDPSIEUSNACO-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- HMPHJJBZKIZRHG-UHFFFAOYSA-N chloromethanesulfonic acid Chemical compound OS(=O)(=O)CCl HMPHJJBZKIZRHG-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 1
- WLHCBQAPPJAULW-UHFFFAOYSA-N 4-methylbenzenethiol Chemical compound CC1=CC=C(S)C=C1 WLHCBQAPPJAULW-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001504 aryl thiols Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004763 sulfides Chemical class 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261648928P | 2012-05-18 | 2012-05-18 | |
| US61/648,928 | 2012-05-18 | ||
| PCT/US2013/041504 WO2013173672A1 (en) | 2012-05-18 | 2013-05-17 | Method for the preparation of thiadiazoles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015517531A JP2015517531A (ja) | 2015-06-22 |
| JP2015517531A5 true JP2015517531A5 (cg-RX-API-DMAC10.html) | 2016-06-30 |
| JP6177894B2 JP6177894B2 (ja) | 2017-08-09 |
Family
ID=49584318
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015512873A Expired - Fee Related JP6177894B2 (ja) | 2012-05-18 | 2013-05-17 | チアジアゾールの調製方法 |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US9296735B2 (cg-RX-API-DMAC10.html) |
| EP (1) | EP2850057A4 (cg-RX-API-DMAC10.html) |
| JP (1) | JP6177894B2 (cg-RX-API-DMAC10.html) |
| CN (1) | CN104736518B (cg-RX-API-DMAC10.html) |
| CA (1) | CA2877026A1 (cg-RX-API-DMAC10.html) |
| IN (1) | IN2014KN02683A (cg-RX-API-DMAC10.html) |
| WO (1) | WO2013173672A1 (cg-RX-API-DMAC10.html) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104788419B (zh) * | 2014-12-30 | 2018-12-21 | 西华大学 | 手性（2，2-二甲基-1，3二氧环戊烷-4-基）羟基甲磺酸盐及其制备方法和应用 |
| CN113454079B (zh) | 2018-12-20 | 2024-07-26 | 拜耳公司 | 作为杀真菌化合物的杂环基哒嗪 |
| AU2021291371A1 (en) | 2020-06-18 | 2023-02-02 | Bayer Aktiengesellschaft | Active compound combinations |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2544562A (en) * | 1947-07-18 | 1951-03-06 | Stanolind Oil & Gas Co | Process for recovering aldehydes and ketones |
| DK36784A (da) * | 1983-02-25 | 1984-08-26 | Hoffmann La Roche | Fremgangsmaade til fremstilling af chirale aldehyder |
| DE19847823A1 (de) * | 1998-10-16 | 2000-04-20 | Aventis Pharma Gmbh | Substituierte Thiadiazolsulfonamide |
| JP4144978B2 (ja) | 1999-09-09 | 2008-09-03 | 富士フイルム株式会社 | １，２，４−チアジアゾール誘導体の合成法 |
| NZ567858A (en) | 2005-11-01 | 2011-08-26 | Array Biopharma Inc | Pyridine compounds useful as Glucokinase activators |
| CN101437512A (zh) | 2006-01-27 | 2009-05-20 | 阿雷生物药品公司 | 葡萄糖激酶活化剂 |
| CN101437816B (zh) | 2006-03-24 | 2013-08-14 | 阿雷生物药品公司 | 作为葡萄糖激酶活性剂的2-氨基吡啶类似物 |
| WO2008091770A1 (en) | 2007-01-24 | 2008-07-31 | Array Biopharma Inc. | 2-aminopyridine derivatives as glucokinase activators |
| US8362037B2 (en) | 2007-03-23 | 2013-01-29 | Array Biopharma, Inc. | 2-aminopyridine analogs as glucokinase activators |
| CA2699718C (en) * | 2007-09-21 | 2014-05-27 | Array Biopharma Inc. | Pyridin-2-yl-amino-1, 2, 4-thiadiazole derivatives as glucokinase activators for the treatment of diabetes mellitus |
| CN101671267B (zh) * | 2009-09-30 | 2012-09-05 | 浙江理工大学 | 一种直接将醛或脂肪族甲基酮的亚硫酸氢钠加成产物转变为相应肟的方法 |
-
2013
- 2013-05-17 US US14/402,069 patent/US9296735B2/en not_active Expired - Fee Related
- 2013-05-17 IN IN2683KON2014 patent/IN2014KN02683A/en unknown
- 2013-05-17 CA CA2877026A patent/CA2877026A1/en not_active Abandoned
- 2013-05-17 WO PCT/US2013/041504 patent/WO2013173672A1/en not_active Ceased
- 2013-05-17 JP JP2015512873A patent/JP6177894B2/ja not_active Expired - Fee Related
- 2013-05-17 EP EP13790539.4A patent/EP2850057A4/en not_active Withdrawn
- 2013-05-17 CN CN201380026364.0A patent/CN104736518B/zh not_active Expired - Fee Related
-
2016
- 2016-02-01 US US15/012,332 patent/US20160221985A1/en not_active Abandoned
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