【０００１】[0001]
【発明の背景】本発明は新規なアルキル置換デンドリマ
ーに関する。本発明のアルキル置換デンドリマーは両親
媒性分子であり、極性官能基を有する材料表面を変性す
るコーティング剤などとして用いることができる。BACKGROUND OF THE INVENTION The present invention relates to novel alkyl-substituted dendrimers. The alkyl-substituted dendrimer of the present invention is an amphipathic molecule and can be used as a coating agent or the like for modifying the surface of a material having a polar functional group.
【０００２】デンドリマーは高度に分岐した三次元構造
を有するポリマーであり、末端を機能性低分子で修飾す
ることにより、様々な機能を付与することが可能であ
り、鎖状のポリマーとは異なる性質を持つと考えられ
る。本発明のアルキル置換デンドリマーはコア部分と置
換基部分とが相溶しない両親媒性分子であり、これら各
部分の位置関係が対応する鎖状ポリマーとは異なる。本
発明のアルキル置換デンドリマーは表面処理剤として用
いることができる。表面処理による機能は主にアルキル
基部分の構造に由来し、例えば撥水機能や液晶配向機能
が得られる。表面処理剤としての機能はデンドリマー分
子の形状に特徴的なものである。例えば、デンドリマー
誘導体、直鎖誘導体(ポリ(エチレンイミン)誘導体)、低
分子誘導体を比較したとき、デンドリマー誘導体のみが
液晶配向処理剤の機能を示す。[0002] Dendrimers are polymers having a highly branched three-dimensional structure, and can be imparted with various functions by modifying the terminal with a functional low-molecular-weight compound. It is thought to have. The alkyl-substituted dendrimer of the present invention is an amphipathic molecule in which the core portion and the substituent portion are incompatible, and the positional relationship between these portions is different from the corresponding linear polymer. The alkyl-substituted dendrimer of the present invention can be used as a surface treatment agent. The function of the surface treatment mainly comes from the structure of the alkyl group portion, and for example, a water repellent function and a liquid crystal alignment function can be obtained. The function as a surface treatment agent is characteristic of the shape of the dendrimer molecule. For example, when a dendrimer derivative, a linear derivative (poly (ethylene imine) derivative), and a low molecular weight derivative are compared, only the dendrimer derivative shows the function of the liquid crystal alignment treatment agent.
【０００３】ポリ(プロピレンイミン)デンドリマーの末
端にアルキル置換基を結合したアルキル置換デンドリマ
ーとしてはMeijerらの例があるが、これは置換基とデン
ドリマーとの結合生成にアミド縮合を用いたものであ
る。これと異なり本発明は、Michael反応用いて非アミ
ド型アルキル置換デンドリマーを得る。An example of an alkyl-substituted dendrimer in which an alkyl substituent is bonded to the terminal of a poly (propylene imine) dendrimer is disclosed by Meijer et al., Which uses amide condensation to form a bond between the substituent and the dendrimer. . In contrast, the present invention uses a Michael reaction to obtain non-amide type alkyl-substituted dendrimers.
【０００４】[0004]
【発明の概要】即ち、本発明は、下式：SUMMARY OF THE INVENTION That is, the present invention provides a compound represented by the following formula:
【化９】Embedded image
【０００５】又は[0005] or
【化１０】Embedded image
【０００６】(式中、Ｒは、(Where R is
【化１１】を意味し、ｎは２〜２０の整数である。)で表されるア
ルキル置換デンドリマーを提供するものである。Embedded image And n is an integer of 2 to 20. ) Is provided.
【０００７】また、本発明は下式：Further, the present invention provides the following formula:
【化１２】Embedded image
【０００８】又は[0008] or
【化１３】Embedded image
【０００９】で表される多官能アミン化合物と下式：A polyfunctional amine compound represented by the following formula:
【化１４】(式中、ｎは前記に同じ。)で表されるアルキル置換アク
リル酸エステル誘導体を、有機溶剤中にて触媒の存在下
または非存在下で反応させることを特徴とするアルキル
置換デンドリマーの製造法に関する。Embedded image Wherein n is the same as defined above, wherein the alkyl-substituted acrylate derivative is reacted in an organic solvent in the presence or absence of a catalyst. About.
【００１０】[0010]
【発明の詳細な開示】本発明のアルキル置換デンドリマ
ーは多官能性アミン化合物をコアとする。かかるコアと
しては、ポリプロピレンイミンデンドリマーＤＡＢ−Ａ
ｍ−４,ポリ(プロピレンイミン)デンドリマー第１世代
(Poly(propyleneimine)Dendrimer,Generation１.０)(式
(IIIa))、ＤＡＢ−Ａｍ−８,ポリ(プロピレンイミン)デ
ンドリマー第２世代(Poly(propyleneimine)Dendrimer,G
eneration２.０)(式(IIIb))(いずれもＤＳＭ社製)など
を用いることができる。これらの化合物はエチレンジア
ミンとアクリロニトリルを出発原料として合成すること
もできる。DETAILED DESCRIPTION OF THE INVENTION The alkyl-substituted dendrimers of the present invention are based on a polyfunctional amine compound. Such cores include polypropylene imine dendrimer DAB-A
m-4, poly (propylene imine) dendrimer first generation
(Poly (propyleneimine) Dendrimer, Generation1.0)
(IIIa)), DAB-Am-8, poly (propyleneimine) dendrimer second generation (Poly (propyleneimine) Dendrimer, G
eneration 2.0) (formula (IIIb)) (all manufactured by DSM) can be used. These compounds can also be synthesized using ethylenediamine and acrylonitrile as starting materials.
【００１１】多官能性アミン化合物であるポリプロピレ
ンイミンデンドリマーの末端は、アルキル置換アクリル
酸エステル誘導体により修飾する。アルキル置換アクリ
ル酸エステル誘導体としては、前記式(IV)で表される化
合物が用いられる。ここでｎは２〜２０、好ましくは６
〜２０である。具体的な化合物としては、オクタデシル
アクリレート、ドデシルアクリレート、オクタデシルメ
タクリレート、ドデシルメタクリレートなどが挙げられ
る。これらのアクリレートは単独で、又は混合して用い
ることができる。The terminal of the polypropyleneimine dendrimer, which is a polyfunctional amine compound, is modified with an alkyl-substituted acrylate derivative. As the alkyl-substituted acrylate derivative, a compound represented by the above formula (IV) is used. Here, n is 2 to 20, preferably 6
-20. Specific compounds include octadecyl acrylate, dodecyl acrylate, octadecyl methacrylate, dodecyl methacrylate, and the like. These acrylates can be used alone or as a mixture.
【００１２】本発明のアルキル置換デンドリマーは、前
記多官能性アミン化合物とアルキル置換アクリル酸エス
テル誘導体を有機溶剤中で反応させることにより得られ
る。アクリル酸エステルの使用量は、多官能アミン[又
はポリ(プロピレンイミン)デンドリマー]１モルに対し
て、ＤＡＢ−Ａｍ−８の場合は１６〜８０モル、好まし
くは１６〜２０モル、ＤＡＢ−Ａｍ−４の場合は８〜４
０モル、好ましくは８〜１０モル、またはアミノ基に対
して２〜１０当量、好ましくは２〜２.５当量(Ａｍ−
８、Ａｍ−４のいずれに対しても)である。The alkyl-substituted dendrimer of the present invention is obtained by reacting the polyfunctional amine compound with an alkyl-substituted acrylate derivative in an organic solvent. The amount of the acrylate used is 16 to 80 mol, preferably 16 to 20 mol, DAB-Am-, in the case of DAB-Am-8, relative to 1 mol of the polyfunctional amine [or poly (propylene imine) dendrimer]. 8 to 4 for 4
0 mol, preferably 8 to 10 mol, or 2 to 10 equivalents, more preferably 2 to 2.5 equivalents (Am-
8, and Am-4).
【００１３】反応溶媒は、これらの溶媒として従来公知
のものがいずれも用いられてよい。具体的にはテトラク
ロロエチレン、１,２−ジクロロエタン、クロロホルム
などのハロゲン化炭化水素；アセトン、メチルエチルケ
トン、メチルイソブチルケトン、シクロヘキサノンなど
のケトン系溶媒；テトラヒドロフラン、ジオキサンなど
の環状エーテル系溶媒、トルエン、キシレンなどの芳香
族炭化水素系溶媒；Ｎ−メチル−２−ピロリドン、Ｎ,
Ｎ−ジメチルホルムアミド、Ｎ,Ｎ−ジメチルアセトア
ミド等の非プロトン性極性溶媒を用いることができる。
これらは単独で用いてもよく、また２種以上を混合して
用いてもよい。As the reaction solvent, any of those conventionally known as these solvents may be used. Specifically, halogenated hydrocarbons such as tetrachloroethylene, 1,2-dichloroethane, and chloroform; ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone; cyclic ether solvents such as tetrahydrofuran and dioxane; and toluene and xylene Aromatic hydrocarbon solvents; N-methyl-2-pyrrolidone, N,
An aprotic polar solvent such as N-dimethylformamide and N, N-dimethylacetamide can be used.
These may be used alone or as a mixture of two or more.
【００１４】反応温度は−５０〜１５０℃、好ましくは
２５〜８０℃である。反応温度が−５０℃未満であると
反応速度が著しく低下し好ましくない。また、１５０℃
を越える反応温度では、多官能性アミン化合物やアルキ
ル置換アクリル酸エステル誘導体の安定性の点で好まし
くない。[0014] The reaction temperature is -50 to 150 ° C, preferably 25 to 80 ° C. If the reaction temperature is lower than −50 ° C., the reaction rate is remarkably reduced, which is not preferable. 150 ° C
If the reaction temperature exceeds, the stability of the polyfunctional amine compound or the alkyl-substituted acrylate derivative is not preferred.
【００１５】反応時間は２〜２００時間、好ましくは、
１８〜９０時間である。これより反応時間が短いと反応
が完全に進行せず好ましくない。反応終了後は溶剤を濃
縮して除去することにより、目的とするアルキル置換デ
ンドリマーを得ることができる。また、メタノール、エ
タノール、イソプロピルアルコール、ヘキサン、トルエ
ンなどの貧溶媒を加えて加熱し、上澄みを除去すること
により精製してもよい。The reaction time is 2 to 200 hours, preferably
18-90 hours. If the reaction time is shorter than this, the reaction does not proceed completely, which is not preferable. After completion of the reaction, the target alkyl-substituted dendrimer can be obtained by concentrating and removing the solvent. Alternatively, purification may be performed by adding a poor solvent such as methanol, ethanol, isopropyl alcohol, hexane, and toluene, heating the mixture, and removing the supernatant.
【００１６】[0016]
【実施例】本発明を実施例及び比較例によりさらに具体
的に説明する。合成はすべて窒素気流下で行った。な
お、得られたアルキル置換デンドリマーの特性は以下の
ようにして測定した。The present invention will be described more specifically with reference to examples and comparative examples. All syntheses were performed under a stream of nitrogen. The properties of the resulting alkyl-substituted dendrimer were measured as follows.
【００１７】１Ｈ ＮＭＲ ＪＮＭ−ＬＡ３００(日本電子(株)製)を用いて測定し
た。ＩＲ ＦＴ／ＩＲ−２３０(日本分光(株)製)を用いて測定し
た。[0017]1 H NMR Measured using JNM-LA300 (manufactured by JEOL Ltd.)
Was.IR Measured using FT / IR-230 (manufactured by JASCO Corporation)
Was.
【００１８】［実施例１］ オクタデシル置換第１世代
プロピレンイミンデンドリマー(ｎ＝１７)の合成 ２０ｍＬの反応容器に、オクタデシルアクリレート(０.
８８ｍｍｏｌ,２８５.６ｍｇ)、ポリ(プロピレンイミ
ン)デンドリマーＤＡＢ−Ａｍ−４(０.１０ｍｍｏｌ,３
１.６ｍｇ)をとり、ジクロロメタン２.０ｍｌを加え、
４０℃で１８時間攪拌した。室温まで冷却した後、この
溶液を激しく攪拌しながらトルエン中に滴下し、生成し
た沈殿を集めることにより目的物を精製した。これを減
圧乾燥し、結晶状の白色固体を収量１５１ｍｇ、収率５
２%で得た。１ＨＮＭＲによりアクリル二重結合の消費
(５.８７,６.２０,６.４８ｐｐｍ)とエステルのαおよ
びβ位のメチレン鎖の生成(２.４７,２.７５ｐｐｍ)が
観測された。ＩＲにより、１７２７.９ｃｍ−１(ＣＯ)
の特性吸収が観測された。Example 1 Synthesis of Octadecyl-Substituted First-Generation Propyleneimine Dendrimer (n = 17) Octadecyl acrylate (0.1%) was placed in a 20 mL reaction vessel.
88 mmol, 285.6 mg), poly (propylene imine) dendrimer DAB-Am-4 (0.10 mmol, 3
1.6 mg), add 2.0 ml of dichloromethane,
Stirred at 40 ° C. for 18 hours. After cooling to room temperature, this solution was dropped into toluene with vigorous stirring, and the resulting precipitate was collected to purify the target product. This was dried under reduced pressure to give 151 mg of a crystalline white solid in a yield of 5 mg.
Obtained at 2%. Consumption of acrylic double bond by1 HNMR
(5.87, 6.20, 6.48 ppm) and the formation of methylene chains at the α and β positions of the ester (2.47, 2.75 ppm) were observed. By IR, 1727.9 cm-1 (CO)
Characteristic absorption was observed.
【００１９】［実施例２］ オクタデシル置換第２世代
プロピレンイミンデンドリマー(ｎ＝１７)の合成 オクタデシルアクリレートとポリ(プロピレンイミン)デ
ンドリマーＤＡＢ−Ａｍ−８を用い、実施例１と同様に
合成した。結晶状の白色固体を収量４８８ｍｇ、収率８
２%で得た。１ＨＮＭＲによりアクリル二重結合の消費
(５.８７,６.２０,６.４８ｐｐｍ)とエステルのαおよ
びβ位のメチレン鎖の生成(２.４７,２.７５ｐｐｍ)が
観測された。ＩＲにより、１７２７.８ｃｍ−１(ＣＯ)
の特性吸収が観測された。Example 2 Synthesis of Octadecyl-Substituted Second-Generation Propyleneimine Dendrimer (n = 17) Synthesis was carried out in the same manner as in Example 1 using octadecylacrylate and poly (propyleneimine) dendrimer DAB-Am-8. 488 mg of a crystalline white solid was obtained in a yield of 8
Obtained at 2%. Consumption of acrylic double bond by1 HNMR
(5.87, 6.20, 6.48 ppm) and the formation of methylene chains at the α and β positions of the ester (2.47, 2.75 ppm) were observed. By IR, 1727.8 cm-1 (CO)
Characteristic absorption was observed.
【００２０】[0020]
【発明の効果】本発明の置換デンドリマーは両親媒性分
子であり、デンドリマー構造の特徴により相溶しない部
分構造間の位置関係が制限されるためにコーティング剤
としての機能が得られる。As described above, the substituted dendrimer of the present invention is an amphipathic molecule, and the feature of the dendrimer structure restricts the positional relationship between the incompatible partial structures, and thus can function as a coating agent.
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| Application Number | Priority Date | Filing Date | Title |
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| JP2000366555AJP2002167368A (en) | 2000-12-01 | 2000-12-01 | Alkyl-substituted dendrimer and method for producing the same |
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000366555AJP2002167368A (en) | 2000-12-01 | 2000-12-01 | Alkyl-substituted dendrimer and method for producing the same |
| Publication Number | Publication Date |
|---|---|
| JP2002167368Atrue JP2002167368A (en) | 2002-06-11 |
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000366555APendingJP2002167368A (en) | 2000-12-01 | 2000-12-01 | Alkyl-substituted dendrimer and method for producing the same |
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|---|---|
| JP (1) | JP2002167368A (en) |
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008158492A (en)* | 2006-12-21 | 2008-07-10 | Samsung Electronics Co Ltd | Spacer and liquid crystal display device including the same |
| JP2009501699A (en)* | 2005-06-15 | 2009-01-22 | マサチューセッツ インスティテュート オブ テクノロジー | Amine-containing lipids and uses thereof |
| US8969353B2 (en) | 2008-11-07 | 2015-03-03 | Massachusetts Institute Of Technology | Aminoalcohol lipidoids and uses thereof |
| US9181321B2 (en) | 2013-03-14 | 2015-11-10 | Shire Human Genetic Therapies, Inc. | CFTR mRNA compositions and related methods and uses |
| US9193827B2 (en) | 2010-08-26 | 2015-11-24 | Massachusetts Institute Of Technology | Poly(beta-amino alcohols), their preparation, and uses thereof |
| US9227917B2 (en) | 2012-08-13 | 2016-01-05 | Massachusetts Institute Of Technology | Amine-containing lipidoids and uses thereof |
| US9238716B2 (en) | 2011-03-28 | 2016-01-19 | Massachusetts Institute Of Technology | Conjugated lipomers and uses thereof |
| US9308281B2 (en) | 2011-06-08 | 2016-04-12 | Shire Human Genetic Therapies, Inc. | MRNA therapy for Fabry disease |
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| JP2023042244A (en)* | 2021-09-14 | 2023-03-27 | 荒川化学工業株式会社 | Water-repellent composition, water-repellent fiber and method for producing water-repellent fiber |
| US12195505B2 (en) | 2018-11-21 | 2025-01-14 | Translate Bio, Inc. | Treatment of cystic fibrosis by delivery of nebulized mRNA encoding CFTR |
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9006487B2 (en) | 2005-06-15 | 2015-04-14 | Massachusetts Institute Of Technology | Amine-containing lipids and uses thereof |
| JP2009501699A (en)* | 2005-06-15 | 2009-01-22 | マサチューセッツ インスティテュート オブ テクノロジー | Amine-containing lipids and uses thereof |
| JP2008158492A (en)* | 2006-12-21 | 2008-07-10 | Samsung Electronics Co Ltd | Spacer and liquid crystal display device including the same |
| US11414393B2 (en) | 2008-11-07 | 2022-08-16 | Massachusetts Institute Of Technology | Aminoalcohol lipidoids and uses thereof |
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| US11951179B2 (en) | 2011-06-08 | 2024-04-09 | Translate Bio, Inc. | Lipid nanoparticle compositions and methods for MRNA delivery |
| US11951180B2 (en) | 2011-06-08 | 2024-04-09 | Translate Bio, Inc. | Lipid nanoparticle compositions and methods for MRNA delivery |
| US11951181B2 (en) | 2011-06-08 | 2024-04-09 | Translate Bio, Inc. | Lipid nanoparticle compositions and methods for mRNA delivery |
| US10507249B2 (en) | 2011-06-08 | 2019-12-17 | Translate Bio, Inc. | Lipid nanoparticle compositions and methods for mRNA delivery |
| US9597413B2 (en) | 2011-06-08 | 2017-03-21 | Shire Human Genetic Therapies, Inc. | Pulmonary delivery of mRNA |
| US11730825B2 (en) | 2011-06-08 | 2023-08-22 | Translate Bio, Inc. | Lipid nanoparticle compositions and methods for mRNA delivery |
| US10238754B2 (en) | 2011-06-08 | 2019-03-26 | Translate Bio, Inc. | Lipid nanoparticle compositions and methods for MRNA delivery |
| US9308281B2 (en) | 2011-06-08 | 2016-04-12 | Shire Human Genetic Therapies, Inc. | MRNA therapy for Fabry disease |
| US11547764B2 (en) | 2011-06-08 | 2023-01-10 | Translate Bio, Inc. | Lipid nanoparticle compositions and methods for MRNA delivery |
| US10413618B2 (en) | 2011-06-08 | 2019-09-17 | Translate Bio, Inc. | Lipid nanoparticle compositions and methods for mRNA delivery |
| US10350303B1 (en) | 2011-06-08 | 2019-07-16 | Translate Bio, Inc. | Lipid nanoparticle compositions and methods for mRNA delivery |
| US11254936B2 (en) | 2012-06-08 | 2022-02-22 | Translate Bio, Inc. | Nuclease resistant polynucleotides and uses thereof |
| US9439968B2 (en) | 2012-08-13 | 2016-09-13 | Massachusetts Institute Of Technology | Amine-containing lipidoids and uses thereof |
| US9227917B2 (en) | 2012-08-13 | 2016-01-05 | Massachusetts Institute Of Technology | Amine-containing lipidoids and uses thereof |
| US11692189B2 (en) | 2013-03-14 | 2023-07-04 | Translate Bio, Inc. | Methods for purification of messenger RNA |
| US11820977B2 (en) | 2013-03-14 | 2023-11-21 | Translate Bio, Inc. | Methods for purification of messenger RNA |
| US9957499B2 (en) | 2013-03-14 | 2018-05-01 | Translate Bio, Inc. | Methods for purification of messenger RNA |
| US11510937B2 (en) | 2013-03-14 | 2022-11-29 | Translate Bio, Inc. | CFTR MRNA compositions and related methods and uses |
| US10876104B2 (en) | 2013-03-14 | 2020-12-29 | Translate Bio, Inc. | Methods for purification of messenger RNA |
| US12234446B2 (en) | 2013-03-14 | 2025-02-25 | Translate Bio, Inc. | Methods for purification of messenger RNA |
| US10420791B2 (en) | 2013-03-14 | 2019-09-24 | Translate Bio, Inc. | CFTR MRNA compositions and related methods and uses |
| US9713626B2 (en) | 2013-03-14 | 2017-07-25 | Rana Therapeutics, Inc. | CFTR mRNA compositions and related methods and uses |
| US9181321B2 (en) | 2013-03-14 | 2015-11-10 | Shire Human Genetic Therapies, Inc. | CFTR mRNA compositions and related methods and uses |
| US9315472B2 (en) | 2013-05-01 | 2016-04-19 | Massachusetts Institute Of Technology | 1,3,5-triazinane-2,4,6-trione derivatives and uses thereof |
| US10959953B2 (en) | 2013-10-22 | 2021-03-30 | Translate Bio, Inc. | Lipid formulations for delivery of messenger RNA |
| US9629804B2 (en) | 2013-10-22 | 2017-04-25 | Shire Human Genetic Therapies, Inc. | Lipid formulations for delivery of messenger RNA |
| US10052284B2 (en) | 2013-10-22 | 2018-08-21 | Translate Bio, Inc. | Lipid formulations for delivery of messenger RNA |
| US11890377B2 (en) | 2013-10-22 | 2024-02-06 | Translate Bio, Inc. | Lipid formulations for delivery of messenger RNA |
| US10208295B2 (en) | 2013-10-22 | 2019-02-19 | Translate Bio, Inc. | MRNA therapy for phenylketonuria |
| US11224642B2 (en) | 2013-10-22 | 2022-01-18 | Translate Bio, Inc. | MRNA therapy for argininosuccinate synthetase deficiency |
| US11377642B2 (en) | 2013-10-22 | 2022-07-05 | Translate Bio, Inc. | mRNA therapy for phenylketonuria |
| US10493031B2 (en) | 2013-10-22 | 2019-12-03 | Translate Bio, Inc. | Lipid formulations for delivery of messenger RNA |
| US9522176B2 (en) | 2013-10-22 | 2016-12-20 | Shire Human Genetic Therapies, Inc. | MRNA therapy for phenylketonuria |
| US12060381B2 (en) | 2014-04-25 | 2024-08-13 | Translate Bio, Inc. | Methods for purification of messenger RNA |
| US11059841B2 (en) | 2014-04-25 | 2021-07-13 | Translate Bio, Inc. | Methods for purification of messenger RNA |
| US11884692B2 (en) | 2014-04-25 | 2024-01-30 | Translate Bio, Inc. | Methods for purification of messenger RNA |
| US9850269B2 (en) | 2014-04-25 | 2017-12-26 | Translate Bio, Inc. | Methods for purification of messenger RNA |
| US10155785B2 (en) | 2014-04-25 | 2018-12-18 | Translate Bio, Inc. | Methods for purification of messenger RNA |
| US10286083B2 (en) | 2014-05-30 | 2019-05-14 | Translate Bio, Inc. | Biodegradable lipids for delivery of nucleic acids |
| US10286082B2 (en) | 2014-05-30 | 2019-05-14 | Translate Bio, Inc. | Biodegradable lipids for delivery of nucleic acids |
| US10022455B2 (en) | 2014-05-30 | 2018-07-17 | Translate Bio, Inc. | Biodegradable lipids for delivery of nucleic acids |
| US10293057B2 (en) | 2014-05-30 | 2019-05-21 | Translate Bio, Inc. | Biodegradable lipids for delivery of nucleic acids |
| US11433144B2 (en) | 2014-05-30 | 2022-09-06 | Translate Bio, Inc. | Biodegradable lipids for delivery of nucleic acids |
| US10493166B2 (en) | 2014-05-30 | 2019-12-03 | Translate Bio, Inc. | Biodegradable lipids for delivery of nucleic acids |
| US10912844B2 (en) | 2014-05-30 | 2021-02-09 | Translate Bio, Inc. | Biodegradable lipids for delivery of nucleic acids |
| US11104652B2 (en) | 2014-06-24 | 2021-08-31 | Translate Bio, Inc. | Stereochemically enriched compositions for delivery of nucleic acids |
| US10138213B2 (en) | 2014-06-24 | 2018-11-27 | Translate Bio, Inc. | Stereochemically enriched compositions for delivery of nucleic acids |
| US9840479B2 (en) | 2014-07-02 | 2017-12-12 | Massachusetts Institute Of Technology | Polyamine-fatty acid derived lipidoids and uses thereof |
| US11253605B2 (en) | 2017-02-27 | 2022-02-22 | Translate Bio, Inc. | Codon-optimized CFTR MRNA |
| US11173190B2 (en) | 2017-05-16 | 2021-11-16 | Translate Bio, Inc. | Treatment of cystic fibrosis by delivery of codon-optimized mRNA encoding CFTR |
| US12084702B2 (en) | 2018-08-24 | 2024-09-10 | Translate Bio, Inc. | Methods for purification of messenger RNA |
| US11174500B2 (en) | 2018-08-24 | 2021-11-16 | Translate Bio, Inc. | Methods for purification of messenger RNA |
| US12195505B2 (en) | 2018-11-21 | 2025-01-14 | Translate Bio, Inc. | Treatment of cystic fibrosis by delivery of nebulized mRNA encoding CFTR |
| JP2023042244A (en)* | 2021-09-14 | 2023-03-27 | 荒川化学工業株式会社 | Water-repellent composition, water-repellent fiber and method for producing water-repellent fiber |
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