JP2017511383A5 - - Google Patents
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- JP2017511383A5 JP2017511383A5 JP2017505695A JP2017505695A JP2017511383A5 JP 2017511383 A5 JP2017511383 A5 JP 2017511383A5 JP 2017505695 A JP2017505695 A JP 2017505695A JP 2017505695 A JP2017505695 A JP 2017505695A JP 2017511383 A5 JP2017511383 A5 JP 2017511383A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- pharmaceutically acceptable
- compound
- type
- substituted
- 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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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 18
- 229930182470 glycoside Natural products 0.000 claims 18
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 15
- 238000000034 method Methods 0.000 claims 14
- 229940002612 prodrug Drugs 0.000 claims 13
- 239000000651 prodrug Substances 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 10
- 239000003814 drug Substances 0.000 claims 10
- 239000002904 solvent Substances 0.000 claims 9
- 229940079593 drug Drugs 0.000 claims 8
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 239000000203 mixture Substances 0.000 claims 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 6
- -1 Z is CH 2 Inorganic materials 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 6
- 229910052731 fluorine Inorganic materials 0.000 claims 6
- 125000004438 haloalkoxy group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 238000002360 preparation method Methods 0.000 claims 6
- 125000006239 protecting group Chemical group 0.000 claims 6
- 239000003513 alkali Substances 0.000 claims 5
- 125000004429 atom Chemical group 0.000 claims 5
- 125000002619 bicyclic group Chemical group 0.000 claims 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 4
- 229910052801 chlorine Inorganic materials 0.000 claims 4
- 239000000460 chlorine Substances 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 241000287463 Phalacrocorax Species 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 3
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 3
- 229910052794 bromium Inorganic materials 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 230000006196 deacetylation Effects 0.000 claims 3
- 238000003381 deacetylation reaction Methods 0.000 claims 3
- 230000000155 isotopic effect Effects 0.000 claims 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 208000002249 Diabetes Complications Diseases 0.000 claims 2
- 206010012655 Diabetic complications Diseases 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 102000000070 Sodium-Glucose Transport Proteins Human genes 0.000 claims 2
- 108010080361 Sodium-Glucose Transport Proteins Proteins 0.000 claims 2
- 229940127003 anti-diabetic drug Drugs 0.000 claims 2
- 239000003472 antidiabetic agent Substances 0.000 claims 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 2
- 125000002346 iodo group Chemical group I* 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 claims 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 229910015900 BF3 Inorganic materials 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims 1
- 238000006751 Mitsunobu reaction Methods 0.000 claims 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008103 glucose Substances 0.000 claims 1
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 1
- 229910052740 iodine Chemical group 0.000 claims 1
- 239000011630 iodine Chemical group 0.000 claims 1
- 208000030159 metabolic disease Diseases 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 239000012046 mixed solvent Substances 0.000 claims 1
- GMBXBKNMMIWUED-UHFFFAOYSA-N n-(2,2,6,6-tetramethylpiperidin-4-yl)-3-[(2,2,6,6-tetramethylpiperidin-4-yl)amino]propanamide Chemical compound C1C(C)(C)NC(C)(C)CC1NCCC(=O)NC1CC(C)(C)NC(C)(C)C1 GMBXBKNMMIWUED-UHFFFAOYSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 claims 1
- 125000001979 organolithium group Chemical group 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 229940121377 sodium-glucose co-transporter inhibitor Drugs 0.000 claims 1
- 238000011282 treatment Methods 0.000 claims 1
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410148116 | 2014-04-14 | ||
| CN201410148116.X | 2014-04-14 | ||
| CN201410392098.XA CN105001213B (zh) | 2014-04-14 | 2014-08-11 | C-芳基糖苷衍生物、其药物组合物、制备方法及应用 |
| CN201410392098.X | 2014-08-11 | ||
| PCT/CN2015/075651 WO2015158206A1 (zh) | 2014-04-14 | 2015-04-01 | C-芳基糖苷衍生物、其药物组合物、制备方法及应用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017511383A JP2017511383A (ja) | 2017-04-20 |
| JP2017511383A5 true JP2017511383A5 (enExample) | 2018-05-17 |
| JP6577569B2 JP6577569B2 (ja) | 2019-09-18 |
Family
ID=54323473
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017505695A Expired - Fee Related JP6577569B2 (ja) | 2014-04-14 | 2015-04-01 | Ｃ−アリールグリコシド誘導体、その薬物組成物、及び調製方法 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9914724B2 (enExample) |
| EP (1) | EP3133071B1 (enExample) |
| JP (1) | JP6577569B2 (enExample) |
| CN (1) | CN105001213B (enExample) |
| WO (1) | WO2015158206A1 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105017236A (zh) * | 2014-04-14 | 2015-11-04 | 上海迪诺医药科技有限公司 | C-芳基糖苷衍生物、其药物组合物、制备方法及应用 |
| CN105001213B (zh) | 2014-04-14 | 2020-08-28 | 上海迪诺医药科技有限公司 | C-芳基糖苷衍生物、其药物组合物、制备方法及应用 |
| SG10201912699RA (en) * | 2015-07-20 | 2020-02-27 | Genzyme Corp | Colony stimulating factor-1 receptor (csf-1r) inhibitors |
| CN106892948B (zh) * | 2015-12-17 | 2022-07-26 | 宜昌东阳光长江药业股份有限公司 | 吡喃葡萄糖基衍生物及其在医药上的应用 |
| CN106928040A (zh) * | 2015-12-31 | 2017-07-07 | 上海医药工业研究院 | Sglt2抑制剂中间体的制备方法 |
| CN107720781B (zh) * | 2017-11-30 | 2018-07-17 | 五莲森之林海藻有限公司 | 一种盐晶颗粒提取设备 |
| CN111465598B (zh) * | 2018-03-30 | 2023-04-21 | 山东丹红制药有限公司 | 作为SGLTs抑制剂的葡糖苷类衍生物及其应用 |
| CN111471032B (zh) * | 2019-01-24 | 2023-08-01 | 北京盈科瑞创新药物研究有限公司 | 一种糖苷类衍生物的合成方法及其中间体和应用 |
| CN111471031B (zh) * | 2019-01-24 | 2023-05-16 | 北京盈科瑞创新药物研究有限公司 | 一种糖苷类衍生物及其制备方法和应用 |
| MY209787A (en) * | 2019-07-26 | 2025-08-04 | Dongbao Purple Star Hangzhou Biopharmaceutical Co Ltd | Sglts/dpp4 inhibitor and application thereof |
| CN111269205B (zh) * | 2020-02-19 | 2023-05-26 | 华侨大学 | 一种c-芳基糖苷化合物的制备方法 |
| CN112961196B (zh) * | 2021-02-07 | 2022-05-31 | 中国人民大学 | 一种糖基和多肽修饰的1,2,3-三唑化合物的制备方法 |
| CN115991702B (zh) * | 2021-12-09 | 2024-02-02 | 珠海市藤栢医药有限公司 | 芳基c-葡萄糖苷衍生物、其制备方法及其用途 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH12000002657B1 (en) * | 1999-10-12 | 2006-02-21 | Bristol Myers Squibb Co | C-aryl glucoside SGLT2 inhibitors |
| US6515117B2 (en) | 1999-10-12 | 2003-02-04 | Bristol-Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| US6683056B2 (en) * | 2000-03-30 | 2004-01-27 | Bristol-Myers Squibb Company | O-aryl glucoside SGLT2 inhibitors and method |
| US6936590B2 (en) | 2001-03-13 | 2005-08-30 | Bristol Myers Squibb Company | C-aryl glucoside SGLT2 inhibitors and method |
| ATE318272T1 (de) | 2001-04-11 | 2006-03-15 | Bristol Myers Squibb Co | Aminosäurekomplexe von c-arylglycosiden zur behandlung von diabetes und verfahren |
| JP2006516257A (ja) | 2003-01-03 | 2006-06-29 | ブリストル−マイヤーズ スクイブ カンパニー | Ｃ−アリールグルコシドｓｇｌｔ２阻害剤の製造法 |
| PL1609785T3 (pl) * | 2003-03-14 | 2016-07-29 | Astellas Pharma Inc | Pochodne c-glikozydowe i ich sole |
| WO2005012326A1 (en) | 2003-08-01 | 2005-02-10 | Tanabe Seiyaku Co., Ltd. | Novel compounds having inhibitory activity against sodium-dependant transporter |
| CA2557801C (en) * | 2004-03-16 | 2013-06-25 | Boehringer Ingelheim International Gmbh | Glucopyranosyl-substituted benzol derivatives, drugs containing said compounds, the use thereof and method for the production thereof |
| EP1874787B1 (en) * | 2005-04-15 | 2009-12-30 | Boehringer Ingelheim International GmbH | Glucopyranosyl-substituted (heteroaryloxy-benzyl)-benzene derivatives as sglt inhibitors |
| WO2011048148A2 (en) | 2009-10-20 | 2011-04-28 | Novartis Ag | Glycoside derivative and uses thereof |
| WO2012025857A1 (en) * | 2010-08-23 | 2012-03-01 | Hetero Research Foundation | Cycloalkyl methoxybenzyl phenyl pyran derivatives as sodium dependent glucose co transporter (sglt2) inhibitors |
| CN102453026A (zh) * | 2010-10-27 | 2012-05-16 | 上海艾力斯医药科技有限公司 | C-芳基葡糖苷衍生物、制备方法及其应用 |
| WO2012109996A1 (zh) * | 2011-02-18 | 2012-08-23 | 上海璎黎科技有限公司 | 一种芳基糖苷类化合物及其制备方法和应用 |
| US9562029B2 (en) * | 2011-06-25 | 2017-02-07 | Xuanzhu Pharma Co., Ltd. | C-glycoside derivatives |
| CN104059042B (zh) * | 2013-03-22 | 2017-02-08 | 正大天晴药业集团股份有限公司 | C-三芳基葡萄糖苷类sglt-2抑制剂 |
| CN105001213B (zh) | 2014-04-14 | 2020-08-28 | 上海迪诺医药科技有限公司 | C-芳基糖苷衍生物、其药物组合物、制备方法及应用 |
| CN105017236A (zh) | 2014-04-14 | 2015-11-04 | 上海迪诺医药科技有限公司 | C-芳基糖苷衍生物、其药物组合物、制备方法及应用 |
-
2014
- 2014-08-11 CN CN201410392098.XA patent/CN105001213B/zh active Active
-
2015
- 2015-04-01 EP EP15780125.9A patent/EP3133071B1/en active Active
- 2015-04-01 US US15/304,493 patent/US9914724B2/en not_active Expired - Fee Related
- 2015-04-01 WO PCT/CN2015/075651 patent/WO2015158206A1/zh not_active Ceased
- 2015-04-01 JP JP2017505695A patent/JP6577569B2/ja not_active Expired - Fee Related
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