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318-98-9

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318-98-9 Usage

Chemical Properties

Off-White to Light-Yellow Cyrstalline Solid

Uses

Different sources of media describe the Uses of 318-98-9 differently. You can refer to the following data:
1. β?Adrenergic blocker. Antihypertensive; antianginal; antiarrhythmic (class II).
2. For the prophylaxis of migraine
3. Propranolol, a β-adrenergic blocker, is most commonly used to reduce blood pressure; treatment of over-active thyroid and some types of tremor; prevention of migraine headaches and some heart-rhythm problems; used to decrease the number of angina attacks (pain from an inadequate oxygen supply to the heart); used after a heart attack to prevent further damage to the heart.
4. (±)-Propranolol hydrochloride has been used:to determine whether autonomic nervous system mediated the promotive effect on skin microcirculation in rat as a non-selective β- receptor blocker to reduce the arrhythmogenic events to study its effect on oxygen-induced retinopathy in mice

Brand name

Inderal (Wyeth); Innopran (Reliant).

General Description

Propranolol hydrochloride is easily soluble in ethanol and water.

Biochem/physiol Actions

Propranolol hydrochloride is a β-adrenoceptor antagonist. Its action at β2 receptor results in bronchoconstriction. Due to its lipophilic nature, propranolol can penetrate to the central nervous system and has a negative effect. It serves as a 5-HT1/5-HT2 serotonin receptor antagonist. Propranolol hydrochloride is useful as an antihypertensive drug, cardiac depressant and also in the treatment of angina pectoris. It decreases the effect of stress and exercise on heart by reducing the rate of contraction and conduction of impulse. It is known to competitively block the action of catecholamines.

Clinical Use

Beta-adrenoceptor blocker: Hypertension Phaeochromocytoma Angina Arrhythmias Anxiety Migraine prophylaxis

Veterinary Drugs and Treatments

While propranolol is used for hypertension, migraine headache prophylaxis, and angina in human patients, it is used primarily in veterinary medicine for its antiarrhythmic effects. Dysrhythmias treated with propranolol include: atrial premature complexes, ventricular premature complexes, supraventricular premature complexes and tachyarrhythmias, ventricular or atrial tachyarrhythmias secondary to digitalis, atrial tachycardia secondary to Wolff-Parkinson-White (WPW) with normal QRS complexes, and atrial fibrillation (generally in combination with digoxin). Propranolol reportedly improves cardiac performance in animals with hypertrophic cardiomyopathy. It has been used to treat systemic hypertension and clinical signs associated with thyrotoxicosis and pheochromocytoma.

Drug interactions

Potentially hazardous interactions with other drugs Anaesthetics: enhanced hypotensive effect; risk of bupivacaine toxicity increased. Analgesics: NSAIDs antagonise hypotensive effect. Anti-arrhythmics: increased risk of myocardial depression and bradycardia; increased risk of bradycardia, myocardial depression and AV block with amiodarone; concentration increased by propafenone and possibly dronedarone; increased risk of myocardial depression and bradycardia with flecainide; increased risk of lidocaine toxicity. Antibacterials: metabolism increased by rifampicin. Antidepressants: enhanced hypotensive effect with MAOIs; concentration increased by fluvoxamine; concentration of imipramine increased. Antihypertensives; enhanced hypotensive effect; increased risk of withdrawal hypertension with clonidine; increased risk of first dose hypotensive effect with post-synaptic alpha-blockers such as prazosin. Antimalarials: increased risk of bradycardia with mefloquine. Antipsychotics enhanced hypotensive effect with phenothiazines; concentration of both drugs increased with chlorpromazine. Calcium-channel blockers: increased risk of bradycardia and AV block with diltiazem; hypotension and heart failure possible with nifedipine and nisoldipine; asystole, severe hypotension and heart failure with verapamil. Cytotoxics: possible increased risk of bradycardia with crizotinib. Diuretics: enhanced hypotensive effect. Fingolimod: possibly increased risk of bradycardia. Moxisylyte: possible severe postural hypotension. Sympathomimetics: severe hypertension with adrenaline and noradrenaline and possibly with dobutamine.

Metabolism

Propranolol is subject to considerable hepatic-tissue binding and first-pass metabolism. It is metabolised in the liver to an active metabolite (4-hydroxypropranolol) and several inactive ones. The metabolites and small amounts of unchanged drug are excreted in the urine.

Check Digit Verification of cas no

The CAS Registry Mumber 318-98-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,1 and 8 respectively; the second part has 2 digits, 9 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 318-98:
(5*3)+(4*1)+(3*8)+(2*9)+(1*8)=69
69 % 10 = 9
So 318-98-9 is a valid CAS Registry Number.
InChI:InChI=1/C16H21NO2.ClH/c1-12(2)17-10-14(18)11-19-16-9-5-7-13-6-3-4-8-15(13)16;/h3-9,12,14,17-18H,10-11H2,1-2H3;1H

318-98-9 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (H26645)  (±)-Propranolol hydrochloride, 99%   

  • 318-98-9

  • 5g

  • 585.0CNY

  • Detail
  • Alfa Aesar

  • (H26645)  (±)-Propranolol hydrochloride, 99%   

  • 318-98-9

  • 25g

  • 1932.0CNY

  • Detail
  • Sigma-Aldrich

  • (P3500000)  Propranolol hydrochloride  European Pharmacopoeia (EP) Reference Standard

  • 318-98-9

  • P3500000

  • 1,880.19CNY

  • Detail
  • Sigma-Aldrich

  • (P3600000)  Propranolol hydrochloride for performance test  European Pharmacopoeia (EP) Reference Standard

  • 318-98-9

  • P3600000

  • 1,880.19CNY

  • Detail
  • Sigma

  • (P0884)  (±)-Propranolol hydrochloride  ≥99% (TLC), powder

  • 318-98-9

  • P0884-1G

  • 402.48CNY

  • Detail
  • Sigma

  • (P0884)  (±)-Propranolol hydrochloride  ≥99% (TLC), powder

  • 318-98-9

  • P0884-25G

  • 5,620.68CNY

  • Detail
  • USP

  • (1576005)  Propranolol hydrochloride  United States Pharmacopeia (USP) Reference Standard

  • 318-98-9

  • 1576005-200MG

  • 4,662.45CNY

  • Detail
  • Cerilliant

  • (P-055)  Propranolol hydrochloride solution  1.0 mg/mL in methanol (as free base), ampule of 1 mL, certified reference material

  • 318-98-9

  • P-055-1ML

  • 366.21CNY

  • Detail
  • Sigma-Aldrich

  • (40543)  (±)-Propranolol hydrochloride  analytical reference material

  • 318-98-9

  • 40543-100MG

  • 553.41CNY

  • Detail

318-98-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name propranolol hydrochloride

1.2 Other means of identification

Product number -
Other names dociton

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:318-98-9 SDS

318-98-9Synthetic route

α-naphthol
90-15-3

α-naphthol

isopropylamine
75-31-0

isopropylamine

1,2-Epoxy-3-bromopropane
3132-64-7

1,2-Epoxy-3-bromopropane

Inderal
318-98-9

Inderal

Conditions
ConditionsYield
Stage #1: α-naphthol; isopropylamine; 1,2-Epoxy-3-bromopropane With potassium carbonate In N,N-dimethyl-formamide; acetone at 20 - 60℃; for 8h;
Stage #2: With hydrogenchloride In water at 0 - 50℃; for 2h; Temperature;
85.8%
propranolol
525-66-6

propranolol

Inderal
318-98-9

Inderal

Conditions
ConditionsYield
Stage #1: propranolol With pyrographite In ethanol for 0.5h; Reflux;
Stage #2: With hydrogenchloride at 4℃; pH=2;
85.1%
With hydrogenchloride In ethanol; water79.7%
3-(1-naphthyloxy)-1,2-epoxypropane
2461-42-9

3-(1-naphthyloxy)-1,2-epoxypropane

isopropylamine
75-31-0

isopropylamine

Inderal
318-98-9

Inderal

Conditions
ConditionsYield
With hydrogenchloride for 16h; Heating;77%
N-(1-methylethyl)-3-(1-naphthalenyloxy)-2-nitroxypropylamine hydrochloride

N-(1-methylethyl)-3-(1-naphthalenyloxy)-2-nitroxypropylamine hydrochloride

Inderal
318-98-9

Inderal

Conditions
ConditionsYield
With phosphate buffer; L-cysteine ethyl ester hydrochloride at 37℃; for 0.25h; pH=7.7; Product distribution; Further Variations:; pH-values; reaction time;
C44H36N4O12P2(2-)*C16H21NO2*H(1+)

C44H36N4O12P2(2-)*C16H21NO2*H(1+)

A

Inderal
318-98-9

Inderal

B

C44H36N4O12P2(2-)

C44H36N4O12P2(2-)

Conditions
ConditionsYield
In d(4)-methanol; water-d2 Equilibrium constant;
α-naphthol
90-15-3

α-naphthol

Inderal
318-98-9

Inderal

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide / 8 h / 35 °C
2.1: sodium tetrahydroborate / methanol / 2 h / 20 °C
3.1: 5,5-dimethyl-1,3-cyclohexadiene / 4 h / 40 °C
4.1: pyrographite / ethanol / 0.5 h / Reflux
4.2: 4 °C / pH 2
View Scheme
1-bromo-3-(1-naphthalenyloxy)-2-propanone
2007-18-3

1-bromo-3-(1-naphthalenyloxy)-2-propanone

Inderal
318-98-9

Inderal

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium tetrahydroborate / methanol / 2 h / 20 °C
2.1: 5,5-dimethyl-1,3-cyclohexadiene / 4 h / 40 °C
3.1: pyrographite / ethanol / 0.5 h / Reflux
3.2: 4 °C / pH 2
View Scheme
Inderal
318-98-9

Inderal

cyclohexanylcarbonyl chloride
2719-27-9

cyclohexanylcarbonyl chloride

O-cyclohexanoylpropranolol hydrochloride

O-cyclohexanoylpropranolol hydrochloride

Conditions
ConditionsYield
In chloroform for 2h; Heating;97%
Inderal
318-98-9

Inderal

acetyl chloride
75-36-5

acetyl chloride

O-acetylpropranolol hydrochloride
4290-58-8

O-acetylpropranolol hydrochloride

Conditions
ConditionsYield
In chloroform for 2h; Heating;93%
pivaloyl chloride
3282-30-2

pivaloyl chloride

Inderal
318-98-9

Inderal

O-pivaloyl-1-(1-naphthyloxy)-3-isopropylaminopropan-2-ol hydrochloride
94769-42-3

O-pivaloyl-1-(1-naphthyloxy)-3-isopropylaminopropan-2-ol hydrochloride

Conditions
ConditionsYield
In chloroform for 2h; Heating;91%
In chloroform for 15h; Heating;60%
Inderal
318-98-9

Inderal

butyryl chloride
141-75-3

butyryl chloride

(+/-)-propranolol butyrate

(+/-)-propranolol butyrate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;91%
Inderal
318-98-9

Inderal

succinic acid monomethylester chloride
1490-25-1

succinic acid monomethylester chloride

Succinic acid 1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester methyl ester; hydrochloride

Succinic acid 1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester methyl ester; hydrochloride

Conditions
ConditionsYield
In chloroform for 2h; Heating;88%
methyl 4-(chlorocarbonyl)butyrate
1501-26-4

methyl 4-(chlorocarbonyl)butyrate

Inderal
318-98-9

Inderal

Pentanedioic acid 1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester methyl ester; hydrochloride

Pentanedioic acid 1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester methyl ester; hydrochloride

Conditions
ConditionsYield
In chloroform for 2h; Heating;87%
acetic anhydride
108-24-7

acetic anhydride

Inderal
318-98-9

Inderal

N-[2-acetyloxy-3-(1-naphthalenyloxy)propyl]-N-(1-methylethyl)acetamide
70153-33-2

N-[2-acetyloxy-3-(1-naphthalenyloxy)propyl]-N-(1-methylethyl)acetamide

Conditions
ConditionsYield
With triethylamine In chloroform at 20℃; for 20h;87%
Inderal
318-98-9

Inderal

isopentanoyl chloride
108-12-3

isopentanoyl chloride

O-isovalerylpropranolol hydrochloride

O-isovalerylpropranolol hydrochloride

Conditions
ConditionsYield
In chloroform for 2h; Heating;85%
Inderal
318-98-9

Inderal

Cyclobutanecarbonyl chloride
5006-22-4

Cyclobutanecarbonyl chloride

Cyclobutanecarboxylic acid 1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester; hydrochloride

Cyclobutanecarboxylic acid 1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester; hydrochloride

Conditions
ConditionsYield
In chloroform for 2h; Heating;85%
Inderal
318-98-9

Inderal

isobutyryl chloride
79-30-1

isobutyryl chloride

O-isobutyrylpropranolol hydrochloride

O-isobutyrylpropranolol hydrochloride

Conditions
ConditionsYield
In chloroform for 2h; Heating;84%
Inderal
318-98-9

Inderal

butyryl chloride
141-75-3

butyryl chloride

O-Butyryl propranolol hydrochloride

O-Butyryl propranolol hydrochloride

Conditions
ConditionsYield
In chloroform for 2h; Heating;84%
Inderal
318-98-9

Inderal

cyclopropanecarboxylic acid chloride
4023-34-1

cyclopropanecarboxylic acid chloride

O-cyclopropanoylpropranolol hydrochloride

O-cyclopropanoylpropranolol hydrochloride

Conditions
ConditionsYield
In chloroform for 2h; Heating;83%
Inderal
318-98-9

Inderal

N-nitrosopropranolol
84418-35-9

N-nitrosopropranolol

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite at 50℃; for 2h;82%
With acetate buffer; sodium nitrite In water at 95℃; for 3h;77%
1-bromo-2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)ethane
854601-80-2

1-bromo-2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)ethane

Inderal
318-98-9

Inderal

C27H43NO7

C27H43NO7

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 45℃; for 20h;81%
Inderal
318-98-9

Inderal

chloropropranolol
47054-95-5

chloropropranolol

Conditions
ConditionsYield
With N-chloro-succinimide; dimethyl sulfoxide In chloroform at 25℃; for 12h; Reagent/catalyst; Schlenk technique;79%
copper(II) acetate monohydrate
6046-93-1

copper(II) acetate monohydrate

Inderal
318-98-9

Inderal

[Cu2(1-(isopropylamino)-3-(1-naphthyloxy)-2-propanol(-1H))2(OAc)2]
796073-45-5

[Cu2(1-(isopropylamino)-3-(1-naphthyloxy)-2-propanol(-1H))2(OAc)2]

Conditions
ConditionsYield
With NaOH In methanol; water to soln. of ligand in MeOH equimolar amt. of aq. NaOH soln. added dropwise; to resulting soln. (pH 5-7) soln. of metal salt in MeOH added until the final metal ion:ligand:NaOH molar ratio was 1:2:2; mixt. stirred forfor 120 min at 40°C; ppt. filtered; washed (MeOH/H2O, 1:1 v/v); dried (vac., P4O10) for several ds; elem. anal.;70%
propionyl chloride
79-03-8

propionyl chloride

Inderal
318-98-9

Inderal

O-propionylpropranolol hydrochloride

O-propionylpropranolol hydrochloride

Conditions
ConditionsYield
In chloroform for 2h; Heating;69%
Inderal
318-98-9

Inderal

22-bromo-2,5,8,11,14,17,20-heptaoxadocosane
104518-25-4

22-bromo-2,5,8,11,14,17,20-heptaoxadocosane

C31H51NO9

C31H51NO9

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 45℃; for 22h;69%
2-(2-(2-(2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)acetic acid
101791-31-5

2-(2-(2-(2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)acetic acid

Inderal
318-98-9

Inderal

C33H53NO11
1058180-03-2

C33H53NO11

Conditions
ConditionsYield
With dmap; triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 20h;68%
3-chloro-3-oxopropanoic acid methyl ester
37517-81-0

3-chloro-3-oxopropanoic acid methyl ester

Inderal
318-98-9

Inderal

Malonic acid 1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester methyl ester; hydrochloride

Malonic acid 1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester methyl ester; hydrochloride

Conditions
ConditionsYield
In chloroform for 2h; Heating;67%
3,6,9-trioxadecyl bromide
72593-77-2

3,6,9-trioxadecyl bromide

Inderal
318-98-9

Inderal

C23H35NO5

C23H35NO5

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 45℃; for 22h;66%
Inderal
318-98-9

Inderal

n-valeryl chloride
638-29-9

n-valeryl chloride

O-valerylpropranolol hydrochloride

O-valerylpropranolol hydrochloride

Conditions
ConditionsYield
In chloroform for 2h; Heating;65%
cobalt(II) chloride dihydrate

cobalt(II) chloride dihydrate

Inderal
318-98-9

Inderal

[Co(1-(isopropylamino)-3-(1-naphthyloxy)-2-propanol(-1H))2(H2O)2]
796073-46-6

[Co(1-(isopropylamino)-3-(1-naphthyloxy)-2-propanol(-1H))2(H2O)2]

Conditions
ConditionsYield
With NaOH In water; acetonitrile to soln. of ligand in H2O/MeCN (1/5 v/v) soln. of NaOH added dropwise; soln. of metal salt in MeCN/H2O (5/1, v/v) added; mixt. stirred for 60 min at room temp.; ppt. filtered; washed (MeCN/H2O, 1:1 v/v); dried (vac., P4O10) for several ds; elem. anal.;65%
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
423-39-2

1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane

methyl 4-(1-((triisopropylsilyl)oxy)vinyl)benzoate
1356459-76-1

methyl 4-(1-((triisopropylsilyl)oxy)vinyl)benzoate

Inderal
318-98-9

Inderal

methyl 4-(2-(3-isopropyl-5-((naphthalen-1-yloxy)methyl)-2-(perfluoropropyl)oxazolidin-2-yl)acetyl)benzoate

methyl 4-(2-(3-isopropyl-5-((naphthalen-1-yloxy)methyl)-2-(perfluoropropyl)oxazolidin-2-yl)acetyl)benzoate

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane; acriflavine In acetonitrile for 28h; Inert atmosphere;64%
With 1,4-diaza-bicyclo[2.2.2]octane In acetonitrile at 20℃; for 28h; Inert atmosphere; Irradiation;64%
Inderal
318-98-9

Inderal

1-{[(4-nitrophenoxy)carbonyl]oxy}ethyl acetate
101623-68-1

1-{[(4-nitrophenoxy)carbonyl]oxy}ethyl acetate

1--N-isopropylamino>-3-(1-naphthyloxy)-2-propanol
99106-37-3

1--N-isopropylamino>-3-(1-naphthyloxy)-2-propanol

Conditions
ConditionsYield
In N,N,N,N,N,N-hexamethylphosphoric triamide Ambient temperature;61%
61%
Cyclopentanecarboxylic acid chloride
4524-93-0

Cyclopentanecarboxylic acid chloride

Inderal
318-98-9

Inderal

Cyclopentanecarboxylic acid 1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester; hydrochloride

Cyclopentanecarboxylic acid 1-(isopropylamino-methyl)-2-(naphthalen-1-yloxy)-ethyl ester; hydrochloride

Conditions
ConditionsYield
In chloroform for 2h; Heating;58%

318-98-9Relevant articles and documents

Preparation method of propranolol hydrochloride

-

Paragraph 0039-0053, (2021/04/03)

The invention discloses a preparation method of propranolol hydrochloride. Thepreparation method comprises the following steps: synthesizing a crude product by a one-pot method, namely in an organic solvent, sequentially carrying out nucleophilic substitution and aminolysis reaction and TLC monitoring reaction in the presence of a catalyst under alkaline conditions by taking 1-naphthol, epoxy bromopropane and isopropylamine as main raw materials, then acidifying to obtain crude propranolol hydrochloride product, and finally refining and purifying the crude product to obtain a propranolol hydrochloride finished product. The purity of the propranolol hydrochloride finished product is 99.8% or above, and the preparation method is short in synthetic route, easy to operate, high in yield, smallin pollution and particularly suitable for industrial production.

Covalent Organic Frameworks with Chirality Enriched by Biomolecules for Efficient Chiral Separation

Zhang, Sainan,Zheng, Yunlong,An, Hongde,Aguila, Briana,Yang, Cheng-Xiong,Dong, Yueyue,Xie, Wei,Cheng, Peng,Zhang, Zhenjie,Chen, Yao,Ma, Shengqian

supporting information, p. 16754 - 16759 (2018/11/27)

The separation of racemic compounds is important in many fields, such as pharmacology and biology. Taking advantage of the intrinsically strong chiral environment and specific interactions featured by biomolecules, here we contribute a general strategy is developed to enrich chirality into covalent organic frameworks (COFs) by covalently immobilizing a series of biomolecules (amino acids, peptides, enzymes) into achiral COFs. Inheriting the strong chirality and specific interactions from the immobilized biomolecules, the afforded biomolecules?COFs serve as versatile and highly efficient chiral stationary phases towards various racemates in both normal and reverse phase of high-performance liquid chromatography (HPLC). The different interactions between enzyme secondary structure and racemates were revealed by surface-enhanced Raman scattering studies, accounting for the observed chiral separation capacity of enzymes?COFs.

Substituted aromatic amino-alcohol compound, and preparation method and application thereof

-

Paragraph 0122-0125, (2019/01/05)

The invention relates to a compound of a formula (I) or pharmaceutically acceptable salts thereof. In the formula (I), Ar is an aryl, a heteroaryl or the aryl or the heteroaryl which is substituted byone or more of C1-C6 alkyl, halogen, hydroxyl, amido, sulfydryl, aryl or heterocyclyl; X is O, NH or S; R is C1-C4 fatty alkyl or the C1-C4 fatty alkyl which is substituted by halogen or phenyl; n equals to 1 to 3. The invention also provides a preparation method and application of the compound of the formula (I) or the pharmaceutically acceptable salts thereof. The compound provided by the invention can be used for treatment of hemangiomas or vascular malformations. (The formula (I) is shown in the description).

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