63610-08-2

Basic information

• Product Name: Indobufen
• Synonyms: (+-)-butyricaci;1-oxo-2-(p-((alpha-ethyl)carboxymethyl)phenyl)isoindoline;4-(1,3-dihydro-1-oxo-2h-isoindol-2-yl)-alpha-ethyl-benzeneaceticacid;INDOBUFEN;2-[4-(1-OXO-1,3-DIHYDRO-ISOINDOL-2-YL)-PHENYL]-BUTYRIC ACID;lndobufen;INDOBNFEN;2-[4-(1-oxo-2-isoindolinyl)phenyl]butyric acid
• CAS NO: 63610-08-2
• Molecular Formula: C₁₈H₁₇NO₃
• Molecular Weight: 295.33
• EINECS: 264-364-4
• Product Categories: Amines;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 63610-08-2.mol

Chemical Properties

• Melting Point: 182-184°
• Boiling Point: 518.1 °C at 760 mmHg
• Flash Point: 267.1 °C
• Appearance: /
• Density: 1.275 g/cm³
• Vapor Pressure: 1.47E-11mmHg at 25°C
• Refractive Index: 1.629
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.39±0.10(Predicted)
• CAS DataBase Reference: Indobufen(CAS DataBase Reference)
• NIST Chemistry Reference: Indobufen(63610-08-2)
• EPA Substance Registry System: Indobufen(63610-08-2)

Safety Data

• Hazardous Substances Data: 63610-08-2(Hazardous Substances Data)

Usage

Uses

Used in Cardiovascular Applications:
Indobufen is used as an antithrombotic agent for preventing blood clot formation in the cardiovascular system. It is particularly effective in treating peripheral artery disease, where it helps improve blood flow and reduce symptoms such as pain and cramping.
Used in Post-Myocardial Infarction Care:
Indobufen is used as an anticoagulant drug and platelet aggregation inhibitor to prevent deep vein thrombosis after a myocardial infarction (heart attack). By inhibiting platelet aggregation, it reduces the risk of further clot formation and potential complications.
Used in Angina Management:
Indobufen is used to block exercise-induced increases in platelet aggregation in patients with angina. This helps to alleviate chest pain and discomfort associated with physical exertion, improving the patient's quality of life and ability to engage in daily activities.
Used in Anti-Inflammatory and Analgesic Applications:
Indobufen's anti-inflammatory and analgesic properties make it useful in managing pain and inflammation associated with various conditions. It can be used as a therapeutic option for patients experiencing inflammation and pain, providing relief and improving overall comfort.

Clinical Use

A reversible but very potent inhibitor of platelet COX-1 activity, was shown to have comparable clinical efficacy to that of aspirin in prevention of DVT after myocardial infarction and in blocking exercise-induced increase in platelet aggregation. In the secondary prevention of thromboembolic events, 100 or 200 mg of indobufen twice daily is as effective as warfarin or aspirin in patients with or without atrial fibrillation. Currently, indobufen is only available for routine clinical use in Europe.

InChI:InChI=1/C18H17NO3/c1-2-15(18(21)22)12-7-9-14(10-8-12)19-11-13-5-3-4-6-16(13)17(19)20/h3-10,15H,2,11H2,1H3,(H,21,22)/t15-/m1/s1

Upstream product

• 7463-53-8 2RS-(4-nitrophenyl)butanoic acid 
• 94232-67-4 2-[4-(1,3-dioxo-2-isoindolinyl)phenyl]butyric acid 
• 943742-86-7 C₁₂H₁₅BrO₂ 
• 496-12-8 isoindoline 
• 2826-24-6 4-bromobenzylidenemalononitrile 
• 36691-01-7 ethyl 2-(4-(1-oxoisoindolin-2-yl)phenyl)acetate 
• 36691-02-8 ethyl 2-(4-(1-oxoisoindolin-2-yl)phenyl)butanoate 
• 100-39-0 benzyl bromide 
• 5438-70-0 ethyl (4-amino-3,5-dibromophenyl)acetate 
• 57960-76-6 ethyl 2-(4-(benzylamino)phenyl)acetate 

Relevant articles and documents

α-Angelica Lactone in a New Role: Facile Access to N-Aryl Tetrahydroisoquinolinones and Isoindolinones via Organocatalytic α-CH2 Oxygenation

A method for the direct oxidation of various N-aryl tetrahydroisoquinolines and isoindolines to the corresponding lactams using α-angelica lactone as a catalyst was developed. The utility of the method was further demonstrated by synthesis of indoprofen and indobufen.

A g-C3N4-based heterogeneous photocatalyst for visible light mediated aerobic benzylic C-H oxygenations

A metal-free heterogeneous photocatalytic system has been developed for highly efficient benzylic C-H oxygenations using oxygen as an oxidant. This visible light mediated oxidation reaction utilizes graphitic carbon nitride (g-C3N4) as a recyclable, nontoxic and low cost photocatalyst. Mild reaction conditions allow for the generation of synthetically and biologically valued isochromannones, phthalides, isoquinolinones, isoindolinones and xanthones from readily accessible alkyl aromatic precursors in good yields. The heterogeneous nature of the g-C3N4 catalytic system enables easy recovery and recycling as well as the use in multiple runs without loss of activity. The synthetic utility of this "green" methodology was further demonstrated by applying in bioactive and drug valued target syntheses.

Microtubing-Reactor-Assisted Aliphatic C?H Functionalization with HCl as a Hydrogen-Atom-Transfer Catalyst Precursor in Conjunction with an Organic Photoredox Catalyst

Chlorine radical, which is classically generated by the homolysis of Cl2 under UV irradiation, can abstract a hydrogen atom from an unactivated C(sp3)?H bond. We herein demonstrate the use of HCl as an effective hydrogen-atom-transfer catalyst precursor activated by an organic acridinium photoredox catalyst under visible-light irradiation for C?H alkylation and allylation. The key to success relied on the utilization of microtubing reactors to maintain the volatile HCl catalyst. This photomediated chlorine-based C?H activation protocol is effective for a variety of unactivated C(sp3)?H bond patterns, even with primary C(sp3)?H bonds, as in ethane. The merit of this strategy is illustrated by rapid access to several pharmaceutical drugs from abundant unfunctionalized alkane feedstocks.

method for preparing indobufen using micro flow reactor

The present invention relates to a method for producing indobufen using ethyl 2-(4-aminophenyl)acetate, which can be industrially purchased, as a starting material and a method for applying the same to a micro flow reactor. According to the present invention, by producing indobufen using a micro flow reactor, the yield and purity of the produced indobufen can be improved, and time spent for the overall production procedure can be reduced. Accordingly, harmful compounds used during the production procedure can be stably used.

Method for preparing indobufen

The invention discloses a method for preparing indobufen; by optimizing the processes such as using a carbon-supported noble metal as a catalyst in hydrogenation reduction, using a suitable organic acid solvent in zinc powder reduction and introducing hydrogen chloride gas, the preparation method of indobufen is simple to perform and high in yield; the whole preparation method is good in safety, environmentally friendly, good for protecting the health of workers and suitable for industrial use, and the purity of prepared indobufen is high.

Isoindoline derivatives for treating pain

Isoindoline derivatives are disclosed, as for instance of the formula: STR1 and methods of preparation of these compounds, such as the reaction of o-cyano-benzylbromide with a compound of formula STR2 and subsequent saponification. The compounds possess analgesic and anti-inflammatory activity.