66635-85-6 Usage
Description
Anirolac is a nonsteroidal anti-inflammatory drug (NSAID) with analgesic properties, used for the management of pain and inflammation.
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
Check Digit Verification of cas no
The CAS Registry Mumber 66635-85-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,6,6,3 and 5 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 66635-85:
(7*6)+(6*6)+(5*6)+(4*3)+(3*5)+(2*8)+(1*5)=156
156 % 10 = 6
So 66635-85-6 is a valid CAS Registry Number.
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)
66635-85-6Relevant 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
Muchowski,Unger,Ackrell,Cheung,Cooper,Cook,Gallegra,Halpern,Koehler,Kluge
, p. 1037 - 1049 (2007/10/02)
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-pyrrole in treating microvascular diseases associated with diabetes
-
, (2008/06/13)
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.
5-Aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acid derivatives and process for the production thereof
-
, (2008/06/13)
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
