53808-88-1

Basic information

• Product Name: lonazolac
• Synonyms: lonazolac;LONAZOLAC CALCIUM;3-(4-Chlorophenyl)-1-phenyl-1H-pyrazole-4-acetic acid
• CAS NO: 53808-88-1
• Molecular Formula: C₁₇H₁₃ClN₂O₂
• Molecular Weight: 312.755
• EINECS: 258-791-5
• Mol File: 53808-88-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 150-151°
• Boiling Point: 525.1°Cat760mmHg
• Flash Point: 271.4°C
• Appearance: /
• Density: 1.3g/cm³
• Vapor Pressure: 7.46E-12mmHg at 25°C
• PKA: 4.3(at 25℃)
• CAS DataBase Reference: lonazolac(CAS DataBase Reference)
• NIST Chemistry Reference: lonazolac(53808-88-1)
• EPA Substance Registry System: lonazolac(53808-88-1)

Safety Data

• Hazardous Substances Data: 53808-88-1(Hazardous Substances Data)

Usage

Originator

Irriten,Tosse,W. Germany,1981

Definition

ChEBI: A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by a 3-(4-chlorophenyl)-1-phenylpyrazol-4-yl group.

Manufacturing Process

17.6 g 1-phenyl-3-(p-chlorophenyl)-pyrazol-4-acetonitrile and 180 ml 25% aqueous hydrochloric acid were mixed and heated to the boiling temperature under reflux for 6 hours. To the mixture was then added dropwise concentrated aqueous sodium hydroxide until the pH of the mixture reached a value in the range from 3 to 5. The free pyrazol-4-acetic acid precipitated thereby was filtered off, redissolved in dilute aqueous sodium hydroxide, the solution cleared by treatment with activated carbon, and the pyrazol-4-acetic acid precipitated by acidifying the solution by the addition of dilute mineral acid, sulfuric acid. The filtered acid was crystallized from a mixture of ethanol and water. 17.1 g 1-phenyl-3-(p-chlorophenyl)pyrazol-4-acetic acid, melting at 148°C to 150°C, were obtained, representing a yield of 91%.

Therapeutic Function

Antiinflammatory

InChI:InChI=1/C17H13ClN2O2/c18-14-8-6-12(7-9-14)17-13(10-16(21)22)11-20(19-17)15-4-2-1-3-5-15/h1-9,11H,10H2,(H,21,22)/p-1

Upstream product

• 55432-07-0 1-phenyl-3-(p-chlorophenyl)-pyrazol-4-acetonitrile 
• 55432-06-9 4-(chloromethyl)-3-(4-chlorophenyl)-1-phenyl-1H-pyrazole 
• 36640-39-8 4-hydroxy-methyl-1-phenyl-3-(p-chlorophenyl)-pyrazol 
• 36663-00-0 1-phenyl-3-(4-chlorophenyl)-4-pyrazolecarboxaldehyde 
• 2829-26-7 N-(4-chlorobenzylidene)-N'-phenylhydrazine 

Downstream Products

• 1402041-61-5 2-(3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl)-N-tosylacetamide 
• 1402041-65-9 2-[3-(1,1'-biphenyl-4-yl)-1-phenyl-1H-pyrazol-4-yl]-N-[(4-methylphenyl)sulfonyl]acetamide 
• 1402041-62-6 2-[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl]-N-(methylsulfonyl)acetamide 
• 1402041-63-7 2-(3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl)-N-(phenylsulfonyl)acetamide 
• 1402041-64-8 2-(3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl)-N-(phenylsulfonyl)acetamide 

Relevant articles and documents

Synthesis of Pyrazoles Utilizing the Ambiphilic Reactivity of Hydrazones

A Br?nsted acid-mediated synthesis of pyrazoles from conjugated hydrazones through a β-protonation/nucleophilic addition/cyclization/aromatization sequence was developed. This protocol utilizing the ambiphilic reactivity of hydrazones enables not only self-condensation but also cross-condensation, affording multisubstituted pyrazoles in high yields, with a broad substrate scope. This sequential reaction proceeds under mild conditions via a simple operation. Moreover, the method can be applied to the synthesis of a nonsteroidal anti-inflammatory drug, Lonazolac.

High molecular weight prodrug derivatives of antiinflammatory drugs

Compounds of the formula 1, PS - O - A - (CH2)n- B - D (1), wherein PS-O represents an alkoxide residue of any of the free hydroxy groups of a polysaccharide (PS-OH) compound with molecular weight (Mw) of from 40,000 to 5,000,000 selected from dextran, carboxymethyl dextran, diethylaminoethyl dextran, starch, hydroxyet-hyl starch, alginates, glycogen, pullullan, agarose, cellulose, chitosan, chitin and carrageenan,A is a carbonyl group or absent,n is zero or a positive integer from 1 to 14,B is oxygen, a carbonyl group, NR wherein R is hydrogen or lower alkyl, or B is absent, and, D is (i) a group of the formula:, R1 - CO - (11), wherein R1-CO- represents the acyl residue of a carboxylic acid drug (R1-COOH) used in the treatment of inflammatory disorders; or (ii) a group of the formula:, R2 - O - (12), wherein R2-O- refers to the C-21 alkoxide residue of a known antiinflammatory steroid (R2-OH) or an alkoxide residue of any other drug or medicament containing a hydroxy functional group used in the treatment of inflammatory disorders; with the proviso that when A is absent, n is 0, and B is absent, then R1-CO- is different from the acyl residue of acetylsalicylic acid;, and non-toxic pharmaceutically acceptable acid addition salts thereof;, and non-toxic pharmaceutically acceptable cation salts thereof. Such compounds are biolabile prodrugs providing controlled release and prolonged duration of action of the parent active antiinflamma-tory agents locally at the administration site after intra-articular, intra-muscular, subcutaneous or extra-dural application while at the same time being highly stable in aqueous solution in the pH range 3--5. After oral administration of such prodrugs the parent drug is liberated selectively in the terminal ileum and the colon over an extended period of time.

Pyrazol-4-acetic acid compounds

Pyrazol-4-acetic acid compounds, such as substituted pyrazol-4-acetic acid, its esters, amides, nitriles and their pharamaceutically acceptable salts and method for the preparation of these compounds are disclosed. The novel compounds are useful analgesics, anti-inflammatory, and antipyretics.