18699-02-0

Basic information

• Product Name: Actarit
• Synonyms: (p-acetamidophenyl)-aceticaci;(p-acetamidophenyl)aceticacid;4-(acetylamino)-benzeneaceticaci;4-n-acetylaminophenylaceticacid;ms932;RARECHEM AL BO 1520;4-(acetylamino)-benzeneacetic acid;[4-(ACETYLAMINO)PHENYL]ACETIC ACID
• CAS NO: 18699-02-0
• Molecular Formula: C₁₀H₁₁NO₃
• Molecular Weight: 193.2
• EINECS: 242-511-3
• Product Categories: Aromatic Phenylacetic Acids and Derivatives;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 18699-02-0.mol

Chemical Properties

• Melting Point: 173-175°C
• Boiling Point: 449.1 °C at 760 mmHg
• Flash Point: 225.4 °C
• Appearance: crystalline solid
• Density: 1.288 g/cm³
• Vapor Pressure: 7.52E-09mmHg at 25°C
• Refractive Index: 1.604
• Storage Temp.: -20°C
• Solubility: DMSO, Ethanol, Methanol
• PKA: 4.34±0.10(Predicted)
• Merck: 14,133
• CAS DataBase Reference: Actarit(CAS DataBase Reference)
• NIST Chemistry Reference: Actarit(18699-02-0)
• EPA Substance Registry System: Actarit(18699-02-0)

Safety Data

• Safety Statements: 24/25
• RTECS: CY1542000
• Hazardous Substances Data: 18699-02-0(Hazardous Substances Data)

Usage

Uses

Actarit is used as an antiarthritic agent for the treatment of chronic rheumatoid arthritis. It is used to prevent and treat the development of articular lesions by modulating the production and serum levels of interleukin-2, which enhances the production of suppressor T-cells in the immune system. This helps in managing the symptoms and progression of chronic rheumatoid arthritis.

Originator

Nippon Shlnyaku;Mltaublshl Kasel (Japan)

Purification Methods

Crystallise the acid from MeOH/Me2CO, aqueous EtOH or H2O. The amide has m 231o (from 50% aqueous EtOH). [Gabriel Chem Ber 15 841 1882, Cerecedo et al. J Biol Chem 42 238 1924, Tramontano et al. J Am Chem Soc 110 2282 1988, Beilstein 14 II 281.]

InChI:InChI=1/C10H11NO3/c1-7(12)11-9-4-2-8(3-5-9)6-10(13)14/h2-5H,6H2,1H3,(H,11,12)(H,13,14)

Upstream product

• 1197-55-3 4-aminophenylacetic acid 
• 108-24-7 acetic anhydride 
• 113180-61-3 4'-(4''-carboxybutyramido)phenyl 4-acetamidophenylacetate 
• 335200-29-8 [4-(2-{4-[2-(4-Acetylamino-phenyl)-acetoxy]-phenyl}-acetoxy)-phenyl]-acetic acid 
• 335200-33-4 {4-[2-(4-{2-[4-(2-{4-[2-(4-Acetylamino-phenyl)-acetoxy]-phenyl}-acetoxy)-phenyl]-acetoxy}-phenyl)-acetoxy]-phenyl}-acetic acid 
• 106664-49-7 4'-acetamidophenyl 4-acetamidophenylacetate 
• 64-19-7 acetic acid 
• 556-18-3 4-aminobenzaldehyde 
• 97562-37-3 4-(2-nitrovinyl)benzenamine 
• 75-36-5 acetyl chloride 
• 127-19-5 N,N-dimethyl acetamide 

Downstream Products

• 5429-45-8 acetic acid-[4-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl)-anilide] 
• 66956-60-3 (4-acetylamino-3-bromo-phenyl)-acetic acid 
• 2901-44-2 trans-2-(4-acetamidocyclohexyl)acetic acid 
• 2901-45-3 (cis-4-acetylamino-cyclohexyl)-acetic acid 
• 23784-25-0 N-(4'-hydroxy-trans-stilben-4-yl)-acetamide 
• 118380-00-0 (4-Acetylamino-phenyl)-acetic acid 2-methyl-quinolin-8-yl ester 
• 118380-05-5 2-(4-Acetylamino-phenyl)-N-(2-methyl-quinolin-8-yl)-acetamide 
• 142613-57-8 (4-Acetylamino-phenyl)-acetic acid vinyl ester 
• 104595-07-5 N-[4-(4-Methyl-2,5-dioxo-2,5-dihydro-furan-3-yl)-phenyl]-acetamide 
• 104594-76-5 N-[4-(2,5-Dioxo-4-phenyl-2,5-dihydro-furan-3-yl)-phenyl]-acetamide 
• 114886-38-3 (4-Acetylamino-phenyl)-acetic acid phenyl ester 
• 628279-14-1 2-(4-Acetylamino-phenyl)-N-(3-allyl-6-amino-1-butyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-acetamide 
• 637335-11-6 2-(4-acetylaminophenyl)-N-[6-amino-3-(2-fluorobenzyl)-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl]acetamide 
• 628279-21-0 2-(4-acetylamino-phenyl)-N-[6-amino-1-butyl-3-(2-methoxy-ethyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-acetamide 

Related news

Short communicationSuppressive effect of Actarit (cas 18699-02-0) on IgA production in mice: Activation of Cd4+ suppressor T-cells in Peyer's patches09/27/2019

We examined the effects of actarit, a new antirheumatic drug, on antibody production after LPS stimulation in mice. Actarit did not affect the proliferative response of B-cells stimulated with LPS or anti-mouse μ-chain antibody plus rIL-4. Lymphocytes in the Peyer's patches (PP) of mice wi...detailed

Relevant articles and documents

HYALURONIC ACID DERIVATIVE AND DRUG CONTAINING THE SAME

The present invention relates to a hyaluronic acid derivative in which an anti-inflammatory drug is bound via a covalent bond, wherein the structure of the hyaluronic acid derivative is represented by following formula (4) or (5): ???????? HA-SP-NSAID?????(4) ???????? HA-SP-DMARD?????(5) wherein HA represents a hyaluronic acid chain; SP represents a spacer residue; NSAID represents a non-steroidal anti-inflammatory drug residue, DMARD represents a disease-modifying anti-rheumatic drug residue, and - represents the covalent bond, wherein the spacer binds to a carboxyl group of the hyaluronic acid via an amide bond and the anti-inflammatory drug selected from non-steroidal anti-inflammatory drugs and disease-modifying anti-rheumatic drugs binds to the spacer via an ester bond, an amide bond or a thioester bond.

Pharmacomodulation of the antimalarial plasmodione: Synthesis of biaryl-and N-arylalkylamine analogues, antimalarial activities and physicochemical properties

With the aim of increasing the structural diversity on the early antimalarial drug plasmodione, an efficient and versatile procedure to prepare a series of biaryl- and N-arylalkylamines as plasmodione analogues is described. Using the naturally occurring and commercially available menadione as starting material, a 2-step sequence using a Kochi-Anderson reaction and subsequent Pd-catalyzed Suzuki-Miyaura coupling was developed to prepare three representative biphenyl derivatives in good yields for antimalarial evaluation. In addition, synthetic methodologies to afford 3-benzylmenadione derivatives bearing a terminal -N(Me)2 or -N(Et)2 in different positions (ortho, meta and para) on the aryl ring of the benzylic chain of plasmodione were investigated through reductive amination was used as the optimal route to prepare these protonable N-arylalkylamine privileged scaffolds. The antimalarial activities were evaluated and discussed in light of their physicochemical properties. Among the newly synthesized compounds, the para-position of the substituent remains the most favourable position on the benzyl chain and the carbamate -NHBoc was found active both in vitro (42 nM versus 29 nM for plasmodione) and in vivo in Plasmodium berghei-infected mice. The measured acido-basic features of these new molecules support the cytosol-food vacuole shuttling properties of non-protonable plasmodione derivatives essential for redox-cycling. These findings may be useful in antimalarial drug optimization.

Method for preparing 4-acetylaminophenylacetic acid

The invention discloses a method for preparing 4-acetylaminophenylacetic acid. The method includes the steps that p-nitrophenylacetic acid, N,N-dimethylacetamide and ammonium chloride are evenly mixed, heating reflux, cooling and crystallizing are conducted, and crystals are obtained to obtain 4-acetylaminophenylacetic acid. The production cost is low, the yield is high, product purity is good, operation is easy, the production period is short, and the method is suitable for industrial mass production.

Boron trifluoride-methanol complex. Mild and powerful reagent for deprotection of acetylated amines. Scope and selectivity

A boron trifluoride-methanol complex demonstrated remarkable deprotection selectivity against commonly used amino-protecting groups in the deacetylation of acetanilides and high sensitivity to the steric hindrance of substrates. The scope and limitations of the reaction were explored.

ROR-GAMMA MODULATORS AND USES THEREOF

The present invention relates to a compound of formula I, or an isotopic form, stereoisomer, a tautomer, a pharmaceutically acceptable salt, a solvate, a polymorph, a prodrug, N-oxide or S-oxide thereof; and processes for their preparation. The invention further relates to pharmaceutical compositions containing the compounds and their use in the treatment of diseases or disorders mediated by RORγ.

A novel method for the synthesis of actarit

The specific synthetic route to synthesize the actarit (4-acetyl-amino phenylacetic acid) by acylation was designed in which p-amino benzaldehyde (a) and nitromethane (b) was used as the raw materials, through Knoevenagel reaction. The selective reduction of potassium borohydride and p-amino phenylacetic acid to be oxidated under the acidic conditions. After optimization of the synthetic conditions, the yield of each step was more than 85 %. The synthesized compound was confirmed by the elemental analysis and nuclear magnetic resonance. Because of the readily available raw materials, simple operations, high yield and avoiding highly toxic reagents in the synthesis of actarit (4-acetyl-amino phenylacetic acid), the synthetic route is suitable for the industrial production.

2-PHENYL BENZOYLAMIDES

Compounds of Formula I that inhibit microsomal triglyceride transfer protein (MTP) and/or apolipoprotein B (Apo B) secretion and their uses in the treatment of diseases linked thereto in animals are described herein.

Microwave-assisted synthesis of amide under solvent-free conditions

An efficient and environmentally friendly synthetic method for the synthesis of primary amides under microwave irradiation was described, in which the primary amine was directly reacted with acid without any catalytic agents. The reaction took place in 8-12-min, which was much shorter than the traditional synthetic methods, with almost quantitative yields. The influential factor of the reaction was discussed. The tautomerization between the carboxylic acid group and the H atom in α-carbon of L-amino acid was observed, presumably a dehydrated intermediate forming from this tautomerized isomer. Copyright Taylor & Francis Group, LLC.

DERIVATIVES OF ACTARIT AND THEIR THERAPEUTIC USE

Compounds that may have anti-inflammatory activity are of general formula wherein X is O or NR1; Y isOorNR1; R2 is OR1 or C,1-4 alkyl substituted with R3, and R2 is optionally substituted With R4; each R1 is the same or different and is H or C1-4 alkyl, or R1 and R2 are joined to form a four to seven-membered ring containing one or more additional heteroatoms selected from O, N and S, and is optionally substituted with R7; R3is OR4, NR5R6 or a four to seven- embered ring which can contain .one or morte heteroatoms selected from O, N and S, and is optionally substituted with R7;R4 is H or C1-4 alkyl optionally substituted with OR8; R5 and R6 are the same or different and are each selected from H and C1-4 alkyl optionally substituted with OR8; R7 is C1-4 alkyl optionally substituted with OR8, halogen, CF3, NR5R6, or S(O)nR9where n is 0-2; each R8 is H or C1-4 alkyl optionally substituted with halogen or OH; and R9 is C1-4 alkyl; and the salts, solvates and hydrates thereof.