JP2002167368A - Alkyl group-substituted dendrimer and method for preparing the same - Google Patents

Alkyl group-substituted dendrimer and method for preparing the same

Info

Publication number
JP2002167368A
JP2002167368A JP2000366555A JP2000366555A JP2002167368A JP 2002167368 A JP2002167368 A JP 2002167368A JP 2000366555 A JP2000366555 A JP 2000366555A JP 2000366555 A JP2000366555 A JP 2000366555A JP 2002167368 A JP2002167368 A JP 2002167368A
Authority
JP
Japan
Prior art keywords
dendrimer
substituted
alkyl
formula
represented
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.)
Pending
Application number
JP2000366555A
Other languages
Japanese (ja)
Inventor
Shu Mochizuki
Naoki Sadayori
周 望月
直樹 貞頼
Original Assignee
Nitto Denko Corp
日東電工株式会社
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nitto Denko Corp, 日東電工株式会社 filed Critical Nitto Denko Corp
Priority to JP2000366555A priority Critical patent/JP2002167368A/en
Publication of JP2002167368A publication Critical patent/JP2002167368A/en
Application status is Pending legal-status Critical

Links

Abstract

PROBLEM TO BE SOLVED: To provide an alkyl group-substituted dendrimer which is an amphiphilc molecule and is suitable as an coating agent for modifying the surface of material having polar functional groups. SOLUTION: This alkyl group-substituted dendrimer is represented by the general formulas (Ia) or (Ib), (wherein, R means the general formula (II); n is an integer of 2 to 20).

Description

【発明の詳細な説明】 DETAILED DESCRIPTION OF THE INVENTION

【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。 Background of the Invention The present invention relates to a novel alkyl-substituted dendrimers. 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。 Alkyl substituted dendrimers of the present invention are amphiphilic molecules can be used as such a coating agent for modifying the material surface 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。 [0002] Dendrimers are polymers having a highly branched, three-dimensional structures, by modifying the ends with functional small molecule, it is possible to impart various functions, different properties than the linear polymer It is believed to have. 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。 Alkyl substituted dendrimers of the present invention are amphiphilic molecules and core portion and substituent moieties incompatible differs from the positional relationship of respective portions corresponding linear polymers. 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。 Alkyl substituted dendrimers of the present invention can be used as a surface treatment agent. 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。 Function by surface treatment is mainly derived from the structure of the alkyl moiety, for example, water repellent and liquid crystal alignment function is obtained. 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。 Functions as a surface treatment agent is characteristic of the shape of the dendrimer molecule. 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。 For example, dendrimer derivatives, linear derivative (poly (ethylene imine) derivatives), when comparing low molecular derivatives, only the dendrimer derivative showing the function of the liquid crystal aligning 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。 [0003] As the poly (propylene imine) alkyl substituted dendrimer attached to an alkyl substituent at the terminal of the dendrimer is an example of Meijer et al., Which is obtained by using the amide condensation to generate binding between the substituent and the dendrimer . 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。 This unlike the present invention, obtaining a non-amide alkyl substituted dendrimers with Michael reaction.

【0004】 [0004]

【発明の概要】即ち、本発明は、下式: SUMMARY OF THE INVENTION That is, the present invention, the following formula:

【化9】 [Omitted]

【0005】又は [0005] or

【化10】 [Of 10]

【0006】(式中、Rは、 [0006] (In the formula, R,

【化11】 [Of 11] を意味し、nは2〜20の整数である。 It means, n is an integer of 2 to 20. )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。 ) Is to provide an alkyl-substituted dendrimer represented by.

【0007】また、本発明は下式: [0007] The present invention also relates to the following formula:

【化12】 [Of 12]

【0008】又は [0008] or

【化13】 [Of 13]

【0009】で表される多官能アミン化合物と下式: [0009] polyfunctional amine compound represented by the following formula:

【化14】 [Of 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。 (Wherein, n same. Above) the alkyl substituted acrylic acid ester derivative represented by the preparation of alkyl-substituted dendrimers, characterized in that the reaction in the presence or absence of a catalyst in an organic solvent on.

【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。 Alkyl substituted dendrimers of Detailed Description of the Invention The present invention is directed to the core polyfunctional amine compound. 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 Such a core, a polypropylene imine dendrimer DAB-A
m−4,ポリ(プロピレンイミン)デンドリマー第1世代 m-4, poly (propylene imine) dendrimer Generation 1
(Poly(propyleneimine)Dendrimer,Generation1.0)(式 (Poly (propyleneimine) Dendrimer, Generation1.0) (formula
(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 (IIIa)), DAB-Am-8, poly (propylene imine) dendrimer Generation 2 (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。 Eneration2.0) or the like can be used (Equation (IIIb)) (all manufactured by DSM). 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。 These compounds can also be synthesized ethylenediamine and acrylonitrile as the starting material.

【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。 [0011] end of the polypropylene imine dendrimer is a multi-functional amine compound is modified by alkyl-substituted acrylic acid ester derivatives. 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。 The alkyl-substituted acrylic acid ester derivative, a compound represented by the formula (IV) is used. ここでnは2〜20、好ましくは6 Where n is 2 to 20, preferably 6
〜20である。 It is 20. 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。 Specific compounds, octadecyl acrylate, dodecyl acrylate, octadecyl methacrylate, and dodecyl methacrylate. 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。 These acrylates may 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。 [0012] alkyl substituted dendrimers of the present invention is obtained by reacting an organic solvent in the polyfunctional amine compound and an alkyl-substituted acrylic acid ester derivatives. 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 The amount of acrylic acid ester, the polyfunctional amine [or poly (propylene imine) dendrimer] to 1 mole, 16 to 80 moles in the case of DAB-Am-8, preferably 16 to 20 mol, DAB-Am- 4 in the case of the 8 to 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− 0 molar, 2-10 equivalents preferably for 8 to 10 mol, or an amino group, preferably 2 to 2.5 equivalents (Am-
8、Am−4のいずれに対しても)である。 8, Am-4 of to any) is.

【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。 [0013] The reaction solvent may conventionally known ones are all used as these solvents. 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, Specifically, tetrachlorethylene, 1,2-dichloroethane, halogenated hydrocarbons such as chloroform; acetone, methyl ethyl ketone, methyl isobutyl ketone, ketone solvents such as cyclohexanone; tetrahydrofuran, cyclic ether solvents such as dioxane, toluene, such as xylene aromatic hydrocarbon solvents; N- methyl-2-pyrrolidone, 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。 N- dimethylformamide, N, can be used aprotic polar solvents such as N- dimethylacetamide.
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。 These may be used alone or may be used in combination of two or more.

【0014】反応温度は−50〜150℃、好ましくは25〜80℃である。 [0014] The reaction temperature is -50 to 150 ° C., preferably from 25 to 80 ° C.. 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。 The reaction rate with the reaction temperature is less than -50 ° C. is significantly decreased undesirably. また、150℃ In addition, 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。 The reaction temperature exceeding, it is not preferred in view of stability of the polyfunctional amine compound or an alkyl-substituted acrylic acid ester derivatives.

【0015】反応時間は2〜200時間、好ましくは、 [0015] The reaction time is from 2 to 200 hours, preferably,
18〜90時間である。 Is 18 to 90 hours. 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。 Reacting with shorter reaction times than this is not preferable not proceed completely. 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。 After completion of the reaction by removing and concentrating the solvent, it is possible to obtain the alkyl-substituted dendrimer of interest. 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。 Further, methanol, ethanol, isopropyl alcohol, hexane, and heated by adding a poor solvent such as toluene, may be purified by 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。 More specifically described by EXAMPLES The present invention examples and comparative examples. 合成はすべて窒素気流下で行った。 All synthesis was conducted in a nitrogen stream. 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 characteristic of the resulting alkyl substituted dendrimers were determined as follows.

【0017】 H NMR [0017] 1 H NMR JNM−LA300(日本電子(株)製)を用いて測定した。 JNM-LA300 (manufactured by JEOL, Ltd.) was used for the measurement. IR IR FT/IR−230(日本分光(株)製)を用いて測定した。 FT / IR-230 (manufactured by JASCO Co., Ltd.) was used for the measurement.

【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. The reaction vessel synthesis 20mL of Example 1 octadecyl substituted first generation propylene imine dendrimers (n = 17), octadecyl acrylate (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 88mmol, 285.6mg), poly (propylene imine) dendrimer DAB-Am-4 (0.10mmol, 3
1.6mg)をとり、ジクロロメタン2.0mlを加え、 Take 1.6 mg), dichloromethane 2.0ml added,
40℃で18時間攪拌した。 And the mixture was stirred for 18 hours at 40 ℃. 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。 After cooling to room temperature, the solution was added dropwise with vigorous stirring in toluene, and purified the target product by collecting the precipitate formed. これを減圧乾燥し、結晶状の白色固体を収量151mg、収率5 This was dried under reduced pressure, yield 151mg of crystalline white solid, yield 5
2%で得た。 It was obtained with 2%. HNMRによりアクリル二重結合の消費 Consumption of acrylic double bonds by 1 HNMR
(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。 (5.87,6.20,6.48ppm) generation and methylene chain α and β-position of the ester (2.47,2.75ppm) was observed. IRにより、1727.9cm −1 (CO) By IR, 1727.9cm -1 (CO)
の特性吸収が観測された。 The characteristic absorption was observed of.

【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。 [0019] [Example 2] Synthesis of octadecyl acrylate and poly (propylene imine) octadecyl substituted second generation propylene imine dendrimers (n = 17) dendrimer DAB-Am-8, was synthesized as in Example 1. 結晶状の白色固体を収量488mg、収率8 Crystalline white solid Yield 488 mg, yield 8
2%で得た。 It was obtained with 2%. HNMRによりアクリル二重結合の消費 Consumption of acrylic double bonds by 1 HNMR
(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。 (5.87,6.20,6.48ppm) generation and methylene chain α and β-position of the ester (2.47,2.75ppm) was observed. IRにより、1727.8cm −1 (CO) By IR, 1727.8cm -1 (CO)
の特性吸収が観測された。 The characteristic absorption was observed of.

【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。 Substituted dendrimers of the present invention, according to the present invention are amphiphilic molecules, function as a coating agent to the positional relationship between the partial structure incompatible with by the features of the dendrimer structure is restricted are obtained.

───────────────────────────────────────────────────── フロントページの続き Fターム(参考) 4H006 AA01 AA02 AB68 AB80 AB99 AC52 BB11 BB12 BB16 BB20 BB24 BB25 4H020 BA02 ────────────────────────────────────────────────── ─── front page of continued F-term (reference) 4H006 AA01 AA02 AB68 AB80 AB99 AC52 BB11 BB12 BB16 BB20 BB24 BB25 4H020 BA02

Claims (4)

    【特許請求の範囲】 [The claims]
  1. 【請求項1】 下式: 【化1】 [Claim 1] the following formula: ## STR1 ## (式中、Rは、 【化2】 (Wherein, R, ## STR2 ## を意味し、nは2〜20の整数である。 Meaning, n is an integer of 2 to 20. )で表されるアルキル置換デンドリマー。 Substituted dendrimer represented by).
  2. 【請求項2】 下式: 【化3】 Wherein the formula: ## STR3 ## で表される多官能アミン化合物と下式: 【化4】 In the polyfunctional amine compound and the formula represented: ## STR4 ## (式中、nは2〜20の整数を意味する。)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請求項1のアルキル置換デンドリマーの製造法。 (Wherein, n represents an integer of 2 to 20.) The alkyl-substituted acrylic acid ester derivative represented by, wherein the reaction is carried out in the presence or absence of a catalyst in an organic solvent according preparation of alkyl-substituted dendrimers claim 1.
  3. 【請求項3】 下式: 【化5】 3. The following formula: ## STR00005 ## (式中、Rは、 【化6】 (In the formula, R, ## STR00006 ## を意味し、nは2〜20の整数である。 It means, n is an integer of 2 to 20. )で表されるアルキル置換デンドリマー。 Substituted dendrimer represented by).
  4. 【請求項4】 下式: 【化7】 4. The following formula: ## STR00007 ## で表される多官能アミン化合物と下式: 【化8】 In the polyfunctional amine compound and the formula represented: embedded image (式中、nは2〜20の整数を意味する。)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存在下あるい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。 (In the formula, n represents an integer of 2 to 20.) The alkyl-substituted acrylic acid ester derivative represented by the alkyl substitution which comprises reacting in the presence of a catalyst or absence in an organic solvent process for the preparation of the dendrimer.
JP2000366555A 2000-12-01 2000-12-01 Alkyl group-substituted dendrimer and method for preparing the same Pending JP2002167368A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2000366555A JP2002167368A (en) 2000-12-01 2000-12-01 Alkyl group-substituted dendrimer and method for preparing the same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP2000366555A JP2002167368A (en) 2000-12-01 2000-12-01 Alkyl group-substituted dendrimer and method for preparing the same

Publications (1)

Publication Number Publication Date
JP2002167368A true JP2002167368A (en) 2002-06-11

Family

ID=18837159

Family Applications (1)

Application Number Title Priority Date Filing Date
JP2000366555A Pending JP2002167368A (en) 2000-12-01 2000-12-01 Alkyl group-substituted dendrimer and method for preparing the same

Country Status (1)

Country Link
JP (1) JP2002167368A (en)

Cited By (16)

* Cited by examiner, † Cited by third party
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 having 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 the use 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
US9315472B2 (en) 2013-05-01 2016-04-19 Massachusetts Institute Of Technology 1,3,5-triazinane-2,4,6-trione derivatives and uses thereof
US9522176B2 (en) 2013-10-22 2016-12-20 Shire Human Genetic Therapies, Inc. MRNA therapy for phenylketonuria
US9629804B2 (en) 2013-10-22 2017-04-25 Shire Human Genetic Therapies, Inc. Lipid formulations for delivery of messenger RNA
US9840479B2 (en) 2014-07-02 2017-12-12 Massachusetts Institute Of Technology Polyamine-fatty acid derived lipidoids and uses thereof
US9850269B2 (en) 2014-04-25 2017-12-26 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
US10022455B2 (en) 2014-05-30 2018-07-17 Translate Bio, Inc. Biodegradable lipids for delivery of nucleic acids
US10138213B2 (en) 2014-06-24 2018-11-27 Translate Bio, Inc. Stereochemically enriched compositions for delivery of nucleic acids

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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 the use thereof
US9006487B2 (en) 2005-06-15 2015-04-14 Massachusetts Institute Of Technology Amine-containing lipids and uses thereof
JP2008158492A (en) * 2006-12-21 2008-07-10 Samsung Electronics Co Ltd Spacer and liquid crystal display device having the same
US9556110B2 (en) 2008-11-07 2017-01-31 Massachusetts Institute Of Technology Aminoalcohol lipidoids and uses thereof
US10189802B2 (en) 2008-11-07 2019-01-29 Massachusetts Institute Of Technology Aminoalcohol lipidoids and uses thereof
US8969353B2 (en) 2008-11-07 2015-03-03 Massachusetts Institute Of Technology Aminoalcohol lipidoids and uses thereof
US9193827B2 (en) 2010-08-26 2015-11-24 Massachusetts Institute Of Technology Poly(beta-amino alcohols), their preparation, and uses thereof
US10117934B2 (en) 2011-03-28 2018-11-06 Massachusetts Institute Of Technology Conjugated lipomers 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
US10238754B2 (en) 2011-06-08 2019-03-26 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
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
US9181321B2 (en) 2013-03-14 2015-11-10 Shire Human Genetic Therapies, Inc. CFTR mRNA compositions and related methods and uses
US9957499B2 (en) 2013-03-14 2018-05-01 Translate Bio, Inc. Methods for purification of messenger RNA
US9713626B2 (en) 2013-03-14 2017-07-25 Rana Therapeutics, 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
US10208295B2 (en) 2013-10-22 2019-02-19 Translate Bio, Inc. MRNA therapy for phenylketonuria
US10052284B2 (en) 2013-10-22 2018-08-21 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
US9522176B2 (en) 2013-10-22 2016-12-20 Shire Human Genetic Therapies, Inc. MRNA therapy for phenylketonuria
US10155785B2 (en) 2014-04-25 2018-12-18 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
US10022455B2 (en) 2014-05-30 2018-07-17 Translate Bio, Inc. Biodegradable lipids for delivery of nucleic acids
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
US10293057B2 (en) 2014-05-30 2019-05-21 Translate Bio, Inc. Biodegradable lipids 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

Similar Documents

Publication Publication Date Title
Born et al. Comb‐like rotaxane polymers containing non‐covalently bound cyclodextrins in the side chains
US5296588A (en) Process of preparing N-substituted aldonamides
US20090306310A1 (en) Method of using click chemistry to functionalize dendrimers
Li et al. Ultrasound induced formation of organogel from a glutamic dendron
US20090069561A1 (en) Click chemistry route to triazole dendrimers
CA2627216C (en) Polynucleotide labelling reagent
Newkome et al. Nanometric dendritic macromolecules: stepwise assembly bydouble (2, 2′: 6′, 2 ″-terpyridine) ruthenium (I) connectivity
CN1649827A (en) Process for preparing highly functionalized gamma-butyrolactams and gamma-amino acids
NL194042C (en) A process for the preparation of 3-phenyl-4-cyanopyrroles.
JP4617292B2 (en) Preparation and their therapeutic use of aryl carbamate derivatives
Shaabani et al. New and efficient synthesis of dialkyl 2-[1-p-nitrophenyl-2-(alkylamino)-2-oxoethyl] malonates
CN106046022A (en) Process for preparing compound having HIV integrase inhibitory activity
CN102665406A (en) Methods for the synthesis of polycyclic guanidine compounds
JP4377594B2 (en) Method for producing a β- alkoxypropionaldehyde amides
JP4544842B2 (en) Method for producing a polyrotaxane
Newkome et al. Improved synthesis of an ethereal tetraamine core for dendrimer construction
Ghosh et al. Synthesis and photoresponsive study of azobenzene centered polyamidoamine dendrimers
US6319187B1 (en) Catalyst and method for amide formation
Štastný et al. Synthesis of (thia) calix [4] arene oligomers: towards calixarene-based dendrimers
ES2320172T3 (en) Process for the production of 5- (4- (4- (5-cyano-3-indolyl) -butyl) -1-piperazinyl) benzofuran-2-carboxamide.
Vériot et al. Synthesis of C3-cyclotriveratrylene ligands for iron (II) and iron (III) coordination
JP4012145B2 (en) Pyrrole - solid phase synthesis of imidazole polyamide
Jayaraman et al. Synthesis of carbohydrate-containing dendrimers. 5. Preparation of dendrimers using unprotected carbohydrates
JP2004517042A (en) Olefin substituted aromatic or manufacturing method of the heteroaromatic
KR101486449B1 (en) Multifunctional forms of polyoxazoline copolymers and drug compositions comprising the same