66635-85-6

Basic information

• Product Name: Anirolac
• Synonyms: Anirolac;2,3-Dihydro-5-(4-methoxybenzoyl)-1H-pyrrolizine-1-carboxylic acid
• CAS NO: 66635-85-6
• Molecular Formula: C₁₆H₁₅NO₄
• Molecular Weight: 285.2946
• Mol File: 66635-85-6.mol

Chemical Properties

• Boiling Point: 532.6°Cat760mmHg
• Flash Point: 275.9°C
• Appearance: /
• Density: 1.33g/cm³
• Vapor Pressure: 3.58E-12mmHg at 25°C
• Refractive Index: 1.636
• PKA: 4.27±0.20(Predicted)
• CAS DataBase Reference: Anirolac(CAS DataBase Reference)
• NIST Chemistry Reference: Anirolac(66635-85-6)
• EPA Substance Registry System: Anirolac(66635-85-6)

Safety Data

• Hazardous Substances Data: 66635-85-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Anirolac is used as an anti-inflammatory and analgesic agent for the treatment of pain and inflammation. It is effective in providing pain relief equivalent to that of Naproxen (N377520), making it a suitable alternative for patients seeking relief from various inflammatory conditions.
Used in Pain Management:
Anirolac is used as a pain reliever for various conditions, including musculoskeletal pain, headaches, and other forms of acute or chronic pain. Its analgesic properties make it a valuable option for patients seeking relief from discomfort and pain.
Used in Inflammation Reduction:
Anirolac is used as an inflammation reducer, helping to alleviate symptoms associated with inflammatory conditions such as arthritis, tendonitis, and other similar ailments. Its anti-inflammatory action aids in reducing swelling, redness, and discomfort associated with these conditions.

Originator

Anirolac,Syntex Inc.

Manufacturing Process

A solution of 1.1 equivalent of N,N-dimethyl-p-methoxybenzamide and 1 equivalent of phosphorous oxychloride in 2 ml of 1,2-dichloroethane is refluxed for 30 minutes. To this solution is added a solution of 1 equivalent of isopropyl 1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate in 2 ml of 1,2- dichloroethane. The reaction mixture is refluxed under an argon atmosphere for 8 hours, treated with equivalent of sodium acetate and refluxed for a further 5 hours. The resultant mixture is then evaporated to dryness and the residue is chromatographed on 12 g of silica gel, eluting with hexane: ethyl acetate (3:1), monitoring the course of the reaction by TLC. Isopropyl 5-pmethoxybenzoyl- 1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate was obtained as an oil. UV, IR, NMR spectrum confirmed the structure of obtained compound. A solution of 1 equivalent of isopropyl 5-p-methoxybenzoyl-1,2-dihydro-3Hpyrrolo[ 1,2-a]pyrrole-1-carboxylate in 10 ml of methanol is treated with a solution of 1 equivalent of potassium carbonate in 5 ml of water. The reaction mixture is refluxed under nitrogen atmosphere for 30 minutes, cooled, and evaporated to dryness. The residue is taken up in 10 ml of 10% aqueous hydrochloric acid and 50 ml of water and the resultant mixture extracted with ethyl acetate (2x50 ml). The combined extracts are dried over magnesium sulfate and evaporated to dryness under reduced pressure. Crystallization of the residue from ethyl acetate-hexane affords 5-p-methoxybenzoyl-1,2- dihydro-3H-pyrrolo[1, 2-a]pyrrole-1-carboxylic acid (anirolac); MP: 187°- 187.5°C.

Therapeutic Function

Antiinflammatory, Analgesic

InChI:InChI=1/C16H15NO4/c1-21-11-4-2-10(3-5-11)15(18)14-7-6-13-12(16(19)20)8-9-17(13)14/h2-7,12H,8-9H2,1H3,(H,19,20)

Upstream product

• 66635-77-6 isopropyl 5-p-methoxybenzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylate 
• 7291-00-1 N,N-dimethyl-4-methoxybenzamide 
• 66635-71-0 i-propyl 1,2-dihydro-3H-pyrrolo<1,2-a>pyrrole-1-carboxylate 

Downstream Products

• 1093808-74-2 2-diazo-1-[5-(4-methoxybenzoyl)-2,3-dihydropyrrolizin-1-yl]ethanone 

Relevant articles and documents

Synthesis and antiinflammatory and analgesic activity of 5-aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids and related compounds

5-Acyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids and the homologous pyridine and azepine derivatives were synthesized and assayed for antiinflammatory and analgesic activity. 5-Benzoyl-1,2-dihydro-3H-pyrrolo-[1,2-a]pyrrole-1-carboxylic acid and the corresponding p-methoxy compound were selected for evaluation as analgesic agents in humans on the basis of their high potency in the mouse phenylquinone writhing assay as well as on their minimal liability to elicit gastrointestinal erosion in rats on chronic administration. Extensive quantitative structure-activity relationship (QSAR) studies of the benzoylpyrrolopyrrolecarboxylic acids have demonstrated that the analgesic (mouse writhing) and antiinflammatory (rat carrageenan paw) potencies of these compounds are satisfactorily correlated with the steric and hydrogen-bonding properties of the benzoyl substituent(s). The 4-vinylbenzoyl compound, which was correctly predicted to be highly active in both assays on this basis, is undergoing advanced pharmacological evaluation in animals as a potential antiinflammatory agent.

Use of pyrrolo pyrroles in treatment of ophthalmic diseases

Certain known pyrroles have been found to be useful in the topical treatment of various ophthalmic diseases in mammals; especially those originating from or associated with inflammation such as, for example, cystoid macular edema, glaucoma, conjunctivitis, uveitis, diabetic retinopathy and eye surgery or trauma.

Use of pyrrolo-pyrrole in treating microvascular diseases associated with diabetes

The present invention concerns a new use of certain pyrrolo-pyrrole compounds of chemical formulas (A), (B), (C), and (D): STR1 for the treatment of microvascular complications associated with diabetes such as, for example, diabetic retinopathy, diabetic nephropathy and diabetic neuropathy. Pyrrolo-pyrrole compounds prevent development, restrain further progress and relieve symptoms of already developed microvascular complications of diabetes.

Process for 5-aroylation of 1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic esters

An improved process for 5-aroylation of 1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic esters and nitriles and for subsequent hydrolysis thereof is disclosed. In the improved process, an aroyl morpholide is reacted with the pyrrolo pyrrole system and the resultant decomposed with base.

5-Aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid derivatives and process for the production thereof

Novel 5-aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid compounds represented by the formula STR1 and the pharmaceutically acceptable, non-toxic esters and salts thereof, wherein R is hydrogen or a lower alkyl group containing from 1 to 4 car