JPWO2018100219A5 - - Google Patents
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- JPWO2018100219A5 JPWO2018100219A5 JP2019528888A JP2019528888A JPWO2018100219A5 JP WO2018100219 A5 JPWO2018100219 A5 JP WO2018100219A5 JP 2019528888 A JP2019528888 A JP 2019528888A JP 2019528888 A JP2019528888 A JP 2019528888A JP WO2018100219 A5 JPWO2018100219 A5 JP WO2018100219A5
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- JP
- Japan
- Prior art keywords
- group
- tert
- alkyl
- butyldimethylsilyloxy
- styryl
- 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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- -1 trimethylsilyloxy Chemical group 0.000 claims description 13
- 150000001720 carbohydrates Chemical class 0.000 claims description 12
- 235000014633 carbohydrates Nutrition 0.000 claims description 12
- 125000005504 styryl group Chemical group 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 206010053643 Neurodegenerative disease Diseases 0.000 claims description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 2
- PQDJYEQOELDLCP-UHFFFAOYSA-N Trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 claims description 2
- 200000000018 inflammatory disease Diseases 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 229960001755 resorcinol Drugs 0.000 claims description 2
- FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 1
- 230000000926 neurological Effects 0.000 claims 1
- 230000001225 therapeutic Effects 0.000 claims 1
- 208000009025 Nervous System Disease Diseases 0.000 description 1
- 206010029305 Neurological disorder Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
Description
R4、R5、およびR6は、直鎖もしくは分岐のC1-C6アルキル、またはフェニル基の中から独立して選択され、R7は直鎖または分岐のC1-C12アルキルであるが、
ただし、R1、R2、およびR3の少なくとも1つがSiR4R5R6基である化合物を、
炎症性疾患、神経疾患、または神経変性疾患の治療または予防のための薬剤の製造に使用することに関する。
R 4 , R 5 , and R 6 are independently selected from linear or branched C 1 -C 6 alkyl or phenyl groups, and R 7 is linear or branched C 1 -C 12 alkyl. There is,
However, compounds in which at least one of R 1 , R 2 , and R 3 is Si R 4 R 5 R 6 groups,
Concerning its use in the manufacture of agents for the treatment or prevention of inflammatory, neurological, or neurodegenerative disorders.
別のより好ましい実施形態では、R3は以下の炭水化物であり、 In another more preferred embodiment, R 3 is the following carbohydrate ,
別のより好ましい実施形態では、R2は以下の炭水化物であり、 In another more preferred embodiment, R 2 is the following carbohydrate ,
R4、R5、およびR6は、直鎖もしくは分岐のC1-C6アルキル、またはフェニル基の中から独立して選択され、R7は直鎖または分岐のC1-C12アルキルであるが、
ただし、R1、R2、およびR3の少なくとも1つがSiR4R5R6基であり、かつ以下の化合物：
-(E)-(5-(4-(トリメチルシリルオキシ)スチリル)-1,3-フェニレン)ビス(オキシ)ビス(トリメチルシラン)、
-(E)-4-(3,5-ビス(トリイソプロピルシリルオキシ)スチリル)フェノール、
-(E)-3-(tert-ブチルジメチルシリルオキシ)-5-(4-(tert-ブチルジメチルシリルオキシ)スチリル)フェノール、
-(E)-4-(3,5-ビス(tert-ブチルジメチルシリルオキシ)スチリル)フェノール、
-(E)-3-(tert-ブチルジメチルシリルオキシ)-5-(4-ヒドロキシスチリル)フェノール、
-(E)-5-(4-(tert-ブチルジメチルシリルオキシ)スチリル)ベンゼン-1,3-ジオール、
-(E)-(5-(4-(tert-ブチルジメチルシリルオキシ)スチリル)-1,3-フェニレン)ビス(オキシ)ビス(tert-ブチルジメチルシラン)のうちの1つではない、化合物に関する。
R 4 , R 5 , and R 6 are independently selected from linear or branched C 1 -C 6 alkyl or phenyl groups, and R 7 is linear or branched C 1 -C 12 alkyl. There is,
However, at least one of R 1 , R 2 , and R 3 is Si R 4 R 5 R 6 groups, and the following compounds:
-(E)-(5-(4- (trimethylsilyloxy) styryl) -1,3-phenylene) bis (oxy) bis (trimethylsilane),
-(E) -4- (3,5-bis (triisopropylsilyloxy) styryl) phenol,
-(E) -3- (tert-butyldimethylsilyloxy) -5-(4- (tert-butyldimethylsilyloxy) styryl) phenol,
-(E) -4- (3,5-bis (tert-butyldimethylsilyloxy) styryl) phenol,
-(E) -3- (tert-butyldimethylsilyloxy) -5- (4-hydroxystyryl) phenol,
-(E) -5- (4- (tert-butyldimethylsilyloxy) styryl) benzene-1,3-diol,
-(E)-(5- (4- (tert-butyldimethylsilyloxy) styryl) -1,3-phenylene) bis (oxy) bis (tert-butyldimethylsilane), not one of the compounds ..
別のより好ましい実施形態では、R3は以下の炭水化物であり、 In another more preferred embodiment, R 3 is the following carbohydrate ,
別のより好ましい実施形態では、R2は以下の炭水化物であり、 In another more preferred embodiment, R 2 is the following carbohydrate ,
Claims (6)
式中、R1、R2、およびR3は、H、SiR4R5R6基、-NH(CO)R7基、または炭水化物の中から独立して選択され、
R4、R5、およびR6は、直鎖もしくは分岐のC1-C6アルキル、またはフェニル基の中から独立して選択され、R7は直鎖または分岐のC1-C12アルキルであるが、
ただし、R1、R2、およびR3の少なくとも1つがSiR4R5R6基である化合物、又は
から成る群より選ばれる化合物
を含む、炎症性疾患、神経疾患、若しくは神経変性疾患の治療または予防組成物。 Equation (I)
In the formula, R 1 , R 2 , and R 3 are independently selected from H, SiR 4 R 5 R 6 , -NH (CO) R 7 , or carbohydrates .
R 4 , R 5 , and R 6 are independently selected from linear or branched C 1 -C 6 alkyl or phenyl groups, and R 7 is linear or branched C 1 -C 12 alkyl. There is,
However, a compound in which at least one of R 1 , R 2 , and R 3 is a Si R 4 R 5 R 6 group, or
A therapeutic or prophylactic composition for an inflammatory disease, a neurological disease, or a neurodegenerative disease, comprising a compound selected from the group consisting of.
から成る群より選ばれる、請求項２に記載の組成物。 R 3 is H, -NH (CO) R 7 , and the following carbohydrates
The composition according to claim 2, which is selected from the group consisting of.
から成る群より選ばれる、請求項４に記載の組成物。 R 2 is H, -NH (CO) R 7 and the following carbohydrates
The composition according to claim 4, which is selected from the group consisting of.
R4、R5、およびR6は、直鎖もしくは分岐のC1-C6アルキル、またはフェニル基から独立して選択され、R7は直鎖または分岐のC1-C12アルキルであるが、ただし、R1、R2、およびR3の少なくとも１つがSiR4R5R6基であり、かつ以下の化合物：
-(E)-(5-(4-(トリメチルシリルオキシ)スチリル)-1,3-フェニレン)ビス(オキシ)ビス(トリメチルシラン)、
-(E)-4-(3,5-ビス(トリイソプロピルシリルオキシ)スチリル)フェノール、
-(E)-3-(tert-ブチルジメチルシリルオキシ)-5-(4-(tert-ブチルジメチルシリルオキシ)スチリル)フェノール、
-(E)-3-(tert-ブチルジメチルシリルオキシ)-5-(4-(tert-ブチルジメチルシリルオキシ)スチリル)フェノール、
-(E)-3-(tert-ブチルジメチルシリルオキシ)-5-(4-ヒドロキシスチリル)フェノール、
-(E)-5-(4-(tert-ブチルジメチルシリルオキシ)スチリル)ベンゼン-1,3-ジオール、
-(E)-(5-(4-(tert-ブチルジメチルシリルオキシ)スチリル)-1,3-フェニレン)ビス(オキシ)ビス(tert-ブチルジメチルシラン)のうちの1つではない、化合物、又は
以下の化合物
Although R 4 , R 5 , and R 6 are selected independently of the linear or branched C 1 -C 6 alkyl, or phenyl group, R 7 is the linear or branched C 1 -C 12 alkyl. However, at least one of R 1 , R 2 , and R 3 is Si R 4 R 5 R 6 groups, and the following compounds:
-(E)-(5-(4- (trimethylsilyloxy) styryl) -1,3-phenylene) bis (oxy) bis (trimethylsilane),
-(E) -4- (3,5-bis (triisopropylsilyloxy) styryl) phenol,
-(E) -3- (tert-butyldimethylsilyloxy) -5-(4- (tert-butyldimethylsilyloxy) styryl) phenol,
-(E) -3- (tert-butyldimethylsilyloxy) -5-(4- (tert-butyldimethylsilyloxy) styryl) phenol,
-(E) -3- (tert-butyldimethylsilyloxy) -5- (4-hydroxystyryl) phenol,
-(E) -5- (4- (tert-butyldimethylsilyloxy) styryl) benzene-1,3-diol,
-(E)-(5- (4- (tert-butyldimethylsilyloxy) styryl) -1,3-phenylene) bis (oxy) bis (tert-butyldimethylsilane), not one of the compounds, Or the following compounds
から成る群より選ばれる、請求項１１記載の化合物。 R 3 is H, -NH (CO) R 7 and below
The compound according to claim 11, which is selected from the group consisting of.
から成る群より選ばれる、請求項１３に記載の化合物。 R 2 is H, -NH (CO) R 7 and below
The compound according to claim 13, which is selected from the group consisting of.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES201631535A ES2674744B1 (en) | 2016-11-30 | 2016-11-30 | SILVERED DERIVATIVES OF RESVERATROL AND ITS USE IN NEURODEGENERATIVE, NEUROLOGICAL OR INFLAMMATORY DISEASES |
| ESP201631535 | 2016-11-30 | ||
| PCT/ES2017/070776 WO2018100219A1 (en) | 2016-11-30 | 2017-11-23 | Silylated derivatives of reservatrol and the use thereof in neurodegenerative, neurological or inflammatory diseases |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| JP2020514249A JP2020514249A (en) | 2020-05-21 |
| JP2020514249A5 JP2020514249A5 (en) | 2021-01-21 |
| JPWO2018100219A5 true JPWO2018100219A5 (en) | 2022-01-14 |
| JP7082977B2 JP7082977B2 (en) | 2022-06-09 |
Family
ID=62241257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019528888A Active JP7082977B2 (en) | 2016-11-30 | 2017-11-23 | Resveratrol silylated derivatives and their use in neurodegenerative, neurological, or inflammatory diseases |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US11365208B2 (en) |
| EP (1) | EP3549929A4 (en) |
| JP (1) | JP7082977B2 (en) |
| CN (1) | CN109996777A (en) |
| AU (1) | AU2017368843B2 (en) |
| CA (1) | CA3044908A1 (en) |
| ES (1) | ES2674744B1 (en) |
| MX (1) | MX2019006169A (en) |
| WO (1) | WO2018100219A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112110966B (en) * | 2020-10-14 | 2023-10-03 | 牛倩 | Resveratrol glycoside derivative, preparation and application |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7705188B2 (en) * | 2002-04-10 | 2010-04-27 | Arizona Board of Regents, a body corporate of the State of Arizona, Acting for and on Behalf of the Arizona State University | Structural modification of resveratrol: sodium resverastatin phosphate |
| WO2003094833A2 (en) * | 2002-05-10 | 2003-11-20 | Orchid Chemicals & Pharmaceuticals Limited | A new stereoselective route to produce tris-o-substituted-(e)-( 3,5-dihydroxyphenyl)-2-(4- hydroxyphenyl)ethene |
| ES2362065B1 (en) * | 2009-12-15 | 2012-05-18 | Consejo Superior De Investigaciones Cient�?Ficas (Csic) | COMPOUNDS WITH ANTI-INFLAMMATORY ACTIVITY. |
| KR101206123B1 (en) * | 2010-11-25 | 2012-11-28 | 영남대학교 산학협력단 | Synthesis method of compound having stilbene skeleton |
| CN102675100A (en) * | 2011-10-31 | 2012-09-19 | 牛婧 | Ester derivatives of resveratrol and medical applications |
| CN103709050A (en) * | 2012-09-28 | 2014-04-09 | 中山大学 | Resveratrol derivative and application thereof in preparing drug for resisting alzheimer's disease |
| JP6262569B2 (en) * | 2014-03-03 | 2018-01-17 | 国立大学法人宇都宮大学 | Resveratrol derivative and tyrosinase activity inhibitor |
| CN103922981B (en) * | 2014-04-21 | 2017-01-04 | 苏州大学 | A kind of compound and application thereof |
| EP3134421B1 (en) * | 2014-04-24 | 2022-04-20 | Institut National de la Santé et de la Recherche Médicale (INSERM) | New lipophenol compounds and uses thereof |
-
2016
- 2016-11-30 ES ES201631535A patent/ES2674744B1/en active Active
-
2017
- 2017-11-23 JP JP2019528888A patent/JP7082977B2/en active Active
- 2017-11-23 MX MX2019006169A patent/MX2019006169A/en unknown
- 2017-11-23 CN CN201780073748.6A patent/CN109996777A/en active Pending
- 2017-11-23 WO PCT/ES2017/070776 patent/WO2018100219A1/en unknown
- 2017-11-23 EP EP17875307.5A patent/EP3549929A4/en active Pending
- 2017-11-23 CA CA3044908A patent/CA3044908A1/en active Pending
- 2017-11-23 AU AU2017368843A patent/AU2017368843B2/en active Active
- 2017-11-23 US US16/465,536 patent/US11365208B2/en active Active
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