JPWO2020068661A5 - - Google Patents
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- JPWO2020068661A5 JPWO2020068661A5 JP2021516806A JP2021516806A JPWO2020068661A5 JP WO2020068661 A5 JPWO2020068661 A5 JP WO2020068661A5 JP 2021516806 A JP2021516806 A JP 2021516806A JP 2021516806 A JP2021516806 A JP 2021516806A JP WO2020068661 A5 JPWO2020068661 A5 JP WO2020068661A5
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- JP
- Japan
- Prior art keywords
- compound
- degrees
- methyl
- formula
- pyran
- 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.)
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- 150000001875 compounds Chemical class 0.000 claims 34
- -1 1-((2- (dimethylamino) ethyl) amino) -2-methyl-1-oxopropan-2-yl Chemical group 0.000 claims 19
- 238000000034 method Methods 0.000 claims 18
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims 16
- 238000002844 melting Methods 0.000 claims 12
- 230000008018 melting Effects 0.000 claims 12
- 239000013078 crystal Substances 0.000 claims 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 7
- 229910052763 palladium Inorganic materials 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 4
- 239000003054 catalyst Substances 0.000 claims 4
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 3
- 229930182821 L-proline Natural products 0.000 claims 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 3
- 208000030159 metabolic disease Diseases 0.000 claims 3
- 229960002429 proline Drugs 0.000 claims 3
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 claims 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 2
- BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- QUMCIHKVKQYNPA-RUZDIDTESA-N C1(CCCCC1)CN1[C@@H](C=2N(C=3C=NC(=NC1=3)NC1=C(C=C(C(=O)NC3CCN(CC3)C)C=C1)OC)C(=NN=2)C)CC Chemical compound C1(CCCCC1)CN1[C@@H](C=2N(C=3C=NC(=NC1=3)NC1=C(C=C(C(=O)NC3CCN(CC3)C)C=C1)OC)C(=NN=2)C)CC QUMCIHKVKQYNPA-RUZDIDTESA-N 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims 2
- 239000003446 ligand Substances 0.000 claims 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 238000000634 powder X-ray diffraction Methods 0.000 claims 2
- 239000012041 precatalyst Substances 0.000 claims 2
- CXNIUSPIQKWYAI-UHFFFAOYSA-N xantphos Chemical compound C=12OC3=C(P(C=4C=CC=CC=4)C=4C=CC=CC=4)C=CC=C3C(C)(C)C2=CC=CC=1P(C=1C=CC=CC=1)C1=CC=CC=C1 CXNIUSPIQKWYAI-UHFFFAOYSA-N 0.000 claims 2
- DTXOOYVEAZDMLE-IKQSSVLVSA-N (3S,4R,5R,6S)-6-(3-chloro-4-methylphenyl)oxane-2,3,4,5-tetrol Chemical compound ClC=1C=C(C=CC=1C)[C@H]1[C@@H]([C@H]([C@@H](C(O1)O)O)O)O DTXOOYVEAZDMLE-IKQSSVLVSA-N 0.000 claims 1
- UCFSYHMCKWNKAH-UHFFFAOYSA-N 4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound CC1(C)OBOC1(C)C UCFSYHMCKWNKAH-UHFFFAOYSA-N 0.000 claims 1
- CMCFCEPFLYRSQG-UHFFFAOYSA-N 5-diphenylphosphanylpentan-2-yl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 CMCFCEPFLYRSQG-UHFFFAOYSA-N 0.000 claims 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 1
- 229910019142 PO4 Inorganic materials 0.000 claims 1
- RYXZOQOZERSHHQ-UHFFFAOYSA-N [2-(2-diphenylphosphanylphenoxy)phenyl]-diphenylphosphane Chemical compound C=1C=CC=C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1OC1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RYXZOQOZERSHHQ-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 229910052796 boron Inorganic materials 0.000 claims 1
- QWINMNANNHVXIR-UHFFFAOYSA-N butan-2-yl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C(C)CC)C1=CC=CC=C1 QWINMNANNHVXIR-UHFFFAOYSA-N 0.000 claims 1
- 150000004651 carbonic acid esters Chemical class 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- 208000016097 disease of metabolism Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 150000002168 ethanoic acid esters Chemical class 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000011065 in-situ storage Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000010452 phosphate Substances 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical group [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201862736871P | 2018-09-26 | 2018-09-26 | |
| US62/736,871 | 2018-09-26 | ||
| PCT/US2019/052414 WO2020068661A1 (en) | 2018-09-26 | 2019-09-23 | Crystalline forms of n-(1 -((2-(dimethylamino)ethyl)amino)-2-m ethyl-1 -oopropan-2-yl)-4-(4-(2-methyl-5- (2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(methylthio)tetrahydro-2h-pyran-2-yl)benzyl) phenl)butanamide and methods of their synthesis |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2022502393A JP2022502393A (ja) | 2022-01-11 |
| JP2022502393A5 JP2022502393A5 (https=) | 2022-03-07 |
| JPWO2020068661A5 true JPWO2020068661A5 (https=) | 2022-03-07 |
Family
ID=68165724
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021516806A Pending JP2022502393A (ja) | 2018-09-26 | 2019-09-23 | Ｎ−（１−（（２−（ジメチルアミノ）エチル）アミノ）−２−メチル−１−オキソプロパン−２−イル）−４−（４−（２−メチル−５−（（２ｓ，３ｒ，４ｒ，５ｓ，６ｒ）−３，４，５−トリヒドロキシ−６−（メチルチオ）テトラヒドロ−２ｈ−ピラン−２−イル）ベンジル）フェニル）ブタンアミドの結晶形態及びそれらの合成方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US10968192B2 (https=) |
| EP (1) | EP3856714A1 (https=) |
| JP (1) | JP2022502393A (https=) |
| KR (1) | KR20210065974A (https=) |
| CN (1) | CN113039176A (https=) |
| AU (1) | AU2019346497A1 (https=) |
| BR (1) | BR112021004839A2 (https=) |
| CA (1) | CA3113037A1 (https=) |
| CO (1) | CO2021005141A2 (https=) |
| IL (1) | IL281728A (https=) |
| MX (1) | MX2021003545A (https=) |
| SG (1) | SG11202102498UA (https=) |
| WO (1) | WO2020068661A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2021227439A1 (zh) * | 2020-05-15 | 2021-11-18 | 上海喆邺生物科技有限公司 | 一种芳基葡糖苷衍生物 |
| ES3040243T3 (en) * | 2020-05-15 | 2025-10-29 | Shanghai Zheye Biotechnology Co Ltd | Aryl glucoside derivative and use thereof in drug |
| CN117018204A (zh) | 2020-07-06 | 2023-11-10 | 诺未科技（北京）有限公司 | 一种治疗癌症的组合物及其应用和药物 |
| WO2025101731A1 (en) | 2023-11-10 | 2025-05-15 | Lexicon Pharmaceuticals, Inc. | Sglt1 inhibitors for use in the treatment of hepatic encephalopathy |
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-
2019
- 2019-09-23 US US16/579,106 patent/US10968192B2/en active Active
- 2019-09-23 CA CA3113037A patent/CA3113037A1/en active Pending
- 2019-09-23 BR BR112021004839-1A patent/BR112021004839A2/pt not_active Application Discontinuation
- 2019-09-23 SG SG11202102498UA patent/SG11202102498UA/en unknown
- 2019-09-23 CN CN201980062714.6A patent/CN113039176A/zh active Pending
- 2019-09-23 WO PCT/US2019/052414 patent/WO2020068661A1/en not_active Ceased
- 2019-09-23 JP JP2021516806A patent/JP2022502393A/ja active Pending
- 2019-09-23 KR KR1020217011819A patent/KR20210065974A/ko not_active Ceased
- 2019-09-23 AU AU2019346497A patent/AU2019346497A1/en not_active Abandoned
- 2019-09-23 MX MX2021003545A patent/MX2021003545A/es unknown
- 2019-09-23 EP EP19783783.4A patent/EP3856714A1/en not_active Withdrawn
-
2021
- 2021-03-22 IL IL281728A patent/IL281728A/en unknown
- 2021-04-22 CO CONC2021/0005141A patent/CO2021005141A2/es unknown
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