雷西莫特 | 144875-48-9
中文名称
雷西莫特
中文别名
4-氨基-2-乙氧基甲基-ALPHA,ALPHA-二甲基-1H-咪唑并[4,5-C]喹啉-1-乙醇；1-(4-氨基-2-(乙氧基甲基)-1H-咪唑并[4,5-C]喹啉-1-基)-2-甲基-2-丙醇
英文名称
resquimod
英文别名
R848；resiquimod；1-(4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-ol；4-amino-2-(ethoxymethyl)-α,α-dimethyl-1H-imidazo[4,5-c]quinoline-1-ethanol；4-amino-α,α-dimethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol；2 (4 amino 2 ethoxymethyl 1h imidazo[4,5 c]quinolin 1 yl) 1,1 dimethylethanol；1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol
CAS
144875-48-9
化学式
C17H22N4O2
mdl
——
分子量
314.387
InChiKey
BXNMTOQRYBFHNZ-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
- 物化性质
- 计算性质
- ADMET
- 安全信息
- SDS
- 制备方法与用途
- 上下游信息
- 文献信息
- 表征谱图
- 同类化合物
- 相关功能分类
- 相关结构分类
物化性质
- 熔点：190-193°
- 沸点：553.6±50.0 °C(Predicted)
- 密度：1.28
- 溶解度：在DMSO中的溶解度为10mg/mL，澄清（加热至60°C）
- 最大波长(λmax)：325nm(lit.)
计算性质
- 辛醇/水分配系数(LogP)：1.3
- 重原子数：23
- 可旋转键数：5
- 环数：3.0
- sp3杂化的碳原子比例：0.41
- 拓扑面积：86.2
- 氢给体数：2
- 氢受体数：5
安全信息
- 危险品运输编号：NONH for all modes of transport
- 海关编码：2933990090
- WGK Germany：3
- RTECS号：NJ5911320
- 危险性防范说明：P261,P305+P351+P338
- 危险性描述：H302,H315,H319,H335
- 储存条件：-20°C下存放于惰性气体中，避免接触湿气（吸湿），并注意防热。
SDS
SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Resiquimod
: SML0196
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 144875-48-9
SECTION 2: Hazards identification
Classification of the substance or mixture
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
Not a hazardous substance or mixture according to EC-directives 67/548/EEC or 1999/45/EC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none
SECTION 3: Composition/information on ingredients
Substances
Synonyms : 4-Amino-2-(ethoxymethyl)-alpha,alpha-dimethyl-1H-imidazo(4,5-
c)quinoline-1-ethanol
R-848
Formula : C17H22N4O2
Molecular Weight : 314,38 g/mol
CAS-No. : 144875-48-9
No components need to be disclosed according to the applicable regulations.
SECTION 4: First aid measures
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
In case of eye contact
Flush eyes with water as a precaution.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available
SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
no data available
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available
SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Avoid dust formation. Avoid breathing vapours, mist or gas.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Sweep up and shovel. Keep in suitable, closed containers for disposal.
Reference to other sections
For disposal see section 13.
SECTION 7: Handling and storage
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Recommended storage temperature: -20 °C
Hygroscopic. Store with desiccant.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated
SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
General industrial hygiene practice.
Personal protective equipment
Eye/face protection
Use equipment for eye protection tested and approved under appropriate government standards
such as NIOSH (US) or EN 166(EU).
Skin protection
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
Body Protection
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.
SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: powder
b) Odour no data available
c) Odour Threshold no data available
d) pH 7,2
e) Melting point/freezing 166 °C
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- log Pow: 2,109
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available
SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5
SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Biochemical:Metabolism (intermediary): Effect on inflammation or mediation of inflammation.
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: NJ5911320
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available
SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company.
Contaminated packaging
Dispose of as unused product.
SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available
SECTION 15: Regulatory information
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
SECTION 16 - ADDITIONAL INFORMATION
N/A
制备方法与用途
用途
体外研究
雷西莫特主要用于科研试剂领域，广泛应用于分子生物学、药理学等科研方面。严禁用于人体。它是一种免疫反应调节剂，并作为有效的TLR7/8激动剂。
生物活性Resiquimod（R-848，S28463）作为一种免疫反应调节剂，用作有效的TLR7/TLR8激动剂，并能诱导TNF-α、IL-6和IFN-α等细胞因子的上调。此外，它还能减少HCV感染。
靶点| Target | Value |
|---|---|
| TLR7 | |
| TLR8 |
Resiquimod能够激活免疫细胞，并通过Toll样受体7(TLR7)-MyD88-依赖性信号通路诱导野生型脾细胞的增殖。此外，它还能调节树突状细胞以增加巨细胞病毒-和HIV-1特异性T细胞应答。Resiquimod还能够诱导髓源性抑制细胞分化为巨噬细胞和树突状细胞，并通过减少免疫抑制性的MDSCs提高癌症免疫治疗的效果。
体内研究在野生型小鼠中，单次腹腔注射50 nmol Resiquimod（i.p.）可引起血清中IFN-α、TNF-α和IL-12浓度增加。而在TLR7-缺失或MyD88-缺失的小鼠中则不会观察到上述细胞因子的水平变化。在过敏性哮喘小鼠模型中，通过鼻内给药20 μg Resiquimod（i.n.）能够减少过敏原诱导的气道反应和炎症。
上下游信息
- 上游原料
中文名称 英文名称 CAS号 化学式 分子量 —— 1-[2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol 144875-99-0 C17H21N3O2 299.373 —— 2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinoline 5-oxide —— C17H21N3O3 315.372 —— 4-chloro-α,α-dimethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol 144876-01-7 C17H20ClN3O2 333.818 - 下游产品
中文名称 英文名称 CAS号 化学式 分子量 —— tert-butyl 6-(2-(1-(4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-yloxy)ethylamino)-6-oxohexylcarbamate —— C30H46N6O5 570.732 —— N-(2-(1-(4-amino-2-(ethoxymethyl)-1H-imidazo[4,5-c]quinolin-1-yl)-2-methylpropan-2-yloxy)ethyl)nicotinamide —— C25H30N6O3 462.552 —— 1-[2-(ethoxymethyl)-1-(2-hydroxy-2-methylpropyl)-1H-imidazo[4,5-c]quinolin-4-yl]pyrrolidine-2,5-dione 1000027-07-5 C21H24N4O4 396.446
反应信息
- 作为反应物：参考文献：名称：[EN] BIS [4-AMINO-2-(ETHOXYMETHYL)-1-(2-HYDROXY-2-METHYLPROPYL)-1H-IMIDAZO[4,5-c]QUINOLIN-5-IUM] 4-[(3-CARBOXYLATO-2-HYDROXYNAPHTHALEN-1-YL)METHYL]-3-HYDROXYNAPHTHALENE-2-CARBOXYLATE COMPOSITIONS AND METHODS
[FR] COMPOSITIONS À BASE DE A[BIS [4-AMINO-2-(ÉTHOXYMÉTHYL)-1-(2-HYDROXY-2-MÉTHYLPROPYL)-1H-IMIDAZO[4,5-C]QUINOLIN-5-IUM]A4-[(3-CARBOXYLATO-2-HYDROXYNAPHTALÉN-1-YL)MÉTHYL]-3-HYDROXYNAPHTALÈNE-2-CARBOXYLATE DE [AA] ET PROCÉDÉS CORRESPONDANTS摘要：一种化合物的化学式：包含该化合物的药物组合物，以及通过向动物投予有效量的该化合物来诱导细胞因子生物合成、治疗动物的病毒感染和/或治疗动物的肿瘤性疾病的方法也被披露。公开号：WO2011084726A1 - 作为产物：描述：4-chloro-α,α-dimethyl-2-ethoxymethyl-1H-imidazo[4,5-c]quinoline-1-ethanol 在 氨 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 雷西莫特参考文献：名称：1-substituted, 2-substituted 1H-imidazo[4,5-c]quinolin-4-amines摘要：本发明揭示了1-取代、2-取代的1H-咪唑并[4,5-c]-喹啉-4-胺化合物。这些化合物作为抗病毒剂，它们诱导干扰素的生物合成，并在动物模型中抑制肿瘤形成。该发明还提供了制备这些化合物的中间体，含有这些化合物的药物组合物，以及使用这些化合物的药理学方法。公开号：US06348462B1
文献信息
- [EN] SUBSTITUTED BENZYLAMINE COMPOUNDS, THEIR USE IN MEDICINE, AND IN PARTICULAR THE TREATMENT OF HEPATITIS C VIRUS (HCV) INFECTION<br/>[FR] COMPOSÉS DE BENZYLAMINE SUBSTITUÉS, LEUR UTILISATION EN MÉDECINE, EN PARTICULIER DANS LE TRAITEMENT D'UNE INFECTION PAR LE VIRUS DE L'HÉPATITE C (VHC)申请人：ASTEX THERAPEUTICS LTD公开号：WO2013064538A1公开（公告）日：2013-05-10The invention provides compounds of the formula (I): or a salt, N-oxide or tautomer thereof, wherein A is CH, CF or nitrogen; E is CH, CF or nitrogen; and R0 is hydrogen or C1-2 alkyl; R1a is selected from CONH2; CO2H; an optionally substituted acyclic C1-8 hydrocarbon group; and an optionally substituted monocyclic carbocyclic or heterocyclic group of 3 to 7 ring members, of which 0, 1, 2, 3 or 4 are heteroatom ring members selected from O, N and S; R2 is selected from hydrogen and a group R2a; R2a is selected from an optionally substituted acyclic d-8 hydrocarbon group; an optionally substituted monocyclic carbocyclic or heterocyclic group of 3 to 7 ring members, of which 0, 1 or 2 ring members are heteroatom ring members selected from O, N and S; and an optionally substituted bicyclic heterocyclic group of 9 or 10 ring members, of which 1 or 2 ring members are nitrogen atoms; wherein at least one of R1 and R2 is other than hydrogen; R3 is an optionally substituted 3- to 10-membered monocyclic or bicyclic carbocyclic or heterocyclic ring containing 0, 1, 2 or 3 heteroatom ring members selected from N, O and S; R4a is selected from halogen; cyano; C1-4 alkyl optionally substituted with one or more fluorine atoms; C1-4 alkoxy optionally substituted with one or more fluorine atoms; hydroxy-C1-4 alkyl; and C1-2 alkoxy-C1-4 alkyl; R5 is selected from hydrogen and a substituent R5a; and R5a is selected from C1-2 alkyl optionally substituted with one or more fluorine atoms; C1-3 alkoxy optionally substituted with one or more fluorine atoms; halogen; cyclopropyl; cyano; and amino, The compounds have activity against hepatitis C virus and can be used in the prevention or treatment of hepatitis C viral infections.该发明提供了以下式（I）的化合物，或其盐、N-氧化物或互变异构体，其中A为CH、CF或氮；E为CH、CF或氮；R0为氢或C1-2烷基；R1a选自CONH2；CO2H；一个可选择取代的非环状C1-8碳氢化合物基团；以及一个可选择取代的含有3至7个环成员的单环碳环或杂环基团，其中0、1、2、3或4个是从O、N和S中选择的杂原子环成员；R2选自氢和一个基团R2a；R2a选自一个可选择取代的非环状d-8碳氢化合物基团；一个可选择取代的含有3至7个环成员的单环碳环或杂环基团，其中0、1或2个环成员是从O、N和S中选择的杂原子环成员；以及一个可选择取代的含有9或10个环成员的双环杂环基团，其中1或2个环成员是氮原子；其中R1和R2中至少一个不是氢；R3选自一个可选择取代的含有0、1、2或3个从N、O和S中选择的杂原子环成员的3至10个成员的单环或双环碳环或杂环环；R4a选自卤素；氰基；C1-4烷基，可选择取代一个或多个氟原子；C1-4烷氧基，可选择取代一个或多个氟原子；羟基-C1-4烷基；和C1-2烷氧基-C1-4烷基；R5选自氢和一个取代基R5a；R5a选自C1-2烷基，可选择取代一个或多个氟原子；C1-3烷氧基，可选择取代一个或多个氟原子；卤素；环丙基；氰基；和氨基。这些化合物对丙型肝炎病毒具有活性，并可用于预防或治疗丙型肝炎病毒感染。
- [EN] DERIVATIVES OF AMANITA TOXINS AND THEIR CONJUGATION TO A CELL BINDING MOLECULE<br/>[FR] DÉRIVÉS DE TOXINES D'AMANITES ET LEUR CONJUGAISON À UNE MOLÉCULE DE LIAISON CELLULAIRE申请人：HANGZHOU DAC BIOTECH CO LTD公开号：WO2017046658A1公开（公告）日：2017-03-23Derivatives of Amernita toxins of Formula (I), wherein, formula (a) R 1, R 2, R 3, R 4, R 5, R 6, R 7, R 8, R 9, R 10, X, L, m, n and Q are defined herein. The preparation of the derivatives. The therapeutic use of the derivatives in the targeted treatment of cancers, autoimmune disorders, and infectious diseases.Amernita毒素的衍生物的化学式（I），其中，化学式（a）中的R 1、R 2、R 3、R 4、R 5、R 6、R 7、R 8、R 9、R 10、X、L、m、n和Q在此处被定义。这些衍生物的制备。这些衍生物在靶向治疗癌症、自身免疫性疾病和传染病中的治疗用途。
- [EN] A CONJUGATE OF A CYTOTOXIC AGENT TO A CELL BINDING MOLECULE WITH BRANCHED LINKERS<br/>[FR] CONJUGUÉ D'UN AGENT CYTOTOXIQUE À UNE MOLÉCULE DE LIAISON CELLULAIRE AVEC DES LIEURS RAMIFIÉS申请人：HANGZHOU DAC BIOTECH CO LTD公开号：WO2020257998A1公开（公告）日：2020-12-30Provided is a conjugation of cytotoxic drug to a cell-binding molecule with a side-chain linker. It provides side-chain linkage methods of making a conjugate of a cytotoxic molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and immunological disorders.提供了一种将细胞毒性药物与一个侧链连接分子结合的共轭物。它提供了制备细胞毒性分子与细胞结合配体的共轭物的侧链连接方法，以及在靶向治疗癌症、感染和免疫性疾病中使用该共轭物的方法。
- [EN] CROSS-LINKED PYRROLOBENZODIAZEPINE DIMER (PBD) DERIVATIVE AND ITS CONJUGATES<br/>[FR] DÉRIVÉ DE DIMÈRE DE PYRROLOBENZODIAZÉPINE RÉTICULÉ (PBD) ET SES CONJUGUÉS申请人：HANGZHOU DAC BIOTECH CO LTD公开号：WO2020006722A1公开（公告）日：2020-01-09A novel cross-linked cytotoxic agents, pyrrolobenzo-diazepine dimer (PBD) derivatives, and their conjugates to a cell-binding molecule, a method for preparation of the conjugates and the therapeutic use of the conjugates.一种新型的交联细胞毒剂，吡咯苯并二氮杂环二聚体（PBD）衍生物，以及它们与细胞结合分子的结合物，一种制备这些结合物的方法以及这些结合物的治疗用途。
- [EN] CYCLIC SULFAMIDE COMPOUNDS AND METHODS OF USING SAME<br/>[FR] COMPOSÉS DE SULFAMIDE CYCLIQUE ET LEURS PROCÉDÉS D'UTILISATION申请人：ASSEMBLY BIOSCIENCES INC公开号：WO2018160878A1公开（公告）日：2018-09-07The present disclosure provides, in part, cyclic sulfamide compounds, and pharmaceutical compositions thereof, useful as modulators of Hepatitis B (HBV) core protein, and methods of treating Hepatitis B (HBV) infection.本公开提供了部分环磺胺化合物及其药物组合物，可用作乙型肝炎（HBV）核心蛋白的调节剂，并用于治疗乙型肝炎（HBV）感染的方法。
同类化合物
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