Development of the technological basis for the production of aceclofenac

2024;
: 140-147
1
Lviv Polytechnic National University
2
Lviv Polytechnic National University
3
Kaunas University of Technology, Kaunas, Lithuania

Aceclofenac drugs are widely used in the global therapeutic practice of inflammatory and painful conditions for the treatment of osteoarthritis, rheumatoid arthritis, and ankylosing spondylitis in various dosage forms. The basics of the technology of domestic industrial batch production of aceclofenac with a capacity of 110 t/year for the production of a number of effective medicines have been developed. A five-stage production process is proposed that will allow the production of a domestic product with a high yield (~ 91%) from commercially available reagents. Material calculations were carried out to determine the consumption rates of raw materials. The types of equipment were selected, and the number of equipment was determined. The basic technological scheme and technological flowchart for the production of aceclofenac are proposed

1. Iupac, Fischer, J., & Ganellin, C. R. (2006). Analogue-based drug discovery. John Wiley & Sons.
https://doi.org/10.1002/3527608001
2. Carron, H., Korbon, G. A., & Rowlingson, J. C. (1984). Regional anesthesia: techniques and clinical applications. https://ci.nii.ac.jp/ncid/BA04431981
3. Bort, R., Ponsoda, X., Carrasco, E., Gómez-Lechón, M. J., & Castell, J. V. (1996). Metabolism of aceclofenac in humans. Drug metabolism and disposition: the biological fate of chemicals, 24(8), 834-841.
4. Karmoker, J. R., Sarkar, S., Joydhar, P., & Chowdhury, S. F. (2016). Comparative in vitro equivalence evaluation of some Aceclofenac generic tablets marketed in Bangladesh. The Pharma Innovation Journal, 5(3), 03-07. https://www.thepharmajournal.com/archives/2016/vol5issue3/PartA/5-1-7.pdf
5. Legrand, E. (2004). Aceclofenac in the management of inflammatory pain. Expert Opinion on Pharmacotherapy, 5(6), 1347-1357. https://doi.org/10.1517/14656566.5.6.1347
https://doi.org/10.1517/14656566.5.6.1347
6. Dooley, M., Spencer, C. M., & Dunn, C. J. (2001). Aceclofenac. Drugs, 61(9), 1351-1378. https://doi.org/10.2165/00003495-200161090-00012
https://doi.org/10.2165/00003495-200161090-00012
7. Aceclofenac. (2023). Drugs.com. https://www.drugs.com/international/aceclofenac.html
8. Hinz, B., Auge, D., Rau, T., Rietbrock, S., Brune, K., & Werner, U. (2003). Simultaneous determination of aceclofenac and three of its metabolites in human plasma by high‐performance liquid chromatography. Biomedical Chromatography, 17(4), 268-275. https://doi.org/10.1002/bmc.243
https://doi.org/10.1002/bmc.243
9. Aceclofenac. (2016). In Elsevier eBooks (p. 18). https://doi.org/10.1016/b978-0-444-53717-1.00214-6
https://doi.org/10.1016/B978-0-444-53717-1.00214-6
10. Schiermeier, S., & Schmidt, P. (2002). Fast dispersible ibuprofen tablets. European Journal of Pharmaceutical Sciences, 15(3), 295-305. https://doi.org/10.1016/s0928-0987(02)00011-8
https://doi.org/10.1016/S0928-0987(02)00011-8
11. Patrick K., Sang K.W. (2001). The method of manufacturing a lyophilized dosage form (U.S. Patent No. 20110229573A1. U.S. Patent and Trade-mark Office. https://worldwide.espacenet.com/patent/search/family/044169183/publicati...
12. Patel, D. K., Dasgupta, S., Dey, S., Ramani, Y. R., Ray, S., & Mazumder, B. (2012). Nanostructured Lipid Carriers (NLC)-Based gel for topical delivery of Aceclofenac: preparation, characterization and in vivo evaluation. Scientia Pharmaceutica, 80(3), 749-764. https://doi.org/10.3797/scipharm.1202-12
https://doi.org/10.3797/scipharm.1202-12
13. Derzhavnyy reyestr likarsʹkykh zasobiv Ukrayiny. URL: http://www.drlz.com.ua (Retrieved: 05.01.2024).
14. PharmaCompass.com. (2024). Aceclofenac API Manufacturers | Suppliers | Exporters | Pharmacompass.com. https://www.pharmacompass.com/listed-active-pharmaceutical-ingredients/a...
15. CAS SciFinderⁿ - Chemical Compound Database. CAS. (2024). Retrieved December 31, 2023, from https://www.cas.org/solutions/cas-scifinder-discovery-platform/cas-scifi...
16. Sydorov Yu.I., Chuyeshov V.I., & Novikov V.P. (2009). Protsesy i aparaty khimiko-farmatsevtychnoyi promyslovosti. Vinnytsya: Nova Knyha.
17. Stasevych M.V., Mylyanych A.O., Strelnykov L.S., Krutskykh, T.V., Buchkevych I.R., Zaytsev O.I., Huzova I.O., Strilets O.P., Hladukh YE.V., & Novikov V.P. (2018). Tekhnolohichne obladnannya biotekhnolohichnoyi i farmatsevtychnoyi promyslovosti. Lʹviv: Novyy Svit-2000.
18. Mylyanych A.O. (2021). Metodychni vkazivky do praktychnykh robit z kursu "Ustatkuvannya ta proektuvannya farmatsevtychnykh vyrobnytstv" dlya studentiv pershoho (bakalavrsʹkoho) rivnya vyshchoyi osvity spetsialʹnosti 226 Farmatsiya, promyslova farmatsiya. Lviv : Vydavnytstvo NU «Lvivska politekhnika».
19. Lunan Pharmaceutical Group Corp. (2018). Preparation of aceclofenac (China Patent No. CN108383745A). European Patent Office. https://worldwide.espacenet.com/patent/search/family/063071328/publicati...
20. Zhejiang University of Technology (2019). Preparation method of aceclofenac, (China Patent No. CN110143891 A). European Patent Office. https://worldwide.espacenet.com/patent/search/family/067592402/publicati...
21. J.B. Chemicals & Pharmaceuticals Ltd. (2005). Process for the preparation of [2-(2,6-dichloroanilino)phenyl]acetoxyacetic acid via hydrolysis of the corresponding tert-butyl ester using styrene-divinylbenzene copolymer sulfonic acids, WO2005073163 A1. World Intellectual Property Organization. https://worldwide.espacenet.com/patent/search/family/034814929/publicati...
22. Prodesfarma SA. (1994). Phenylacetic acid derivatives, process for the preparation thereof and corresponding use (Canada Patent No. CA2111169A1). European Patent Office. https://worldwide.espacenet.com/patent/search/family/008279093/publicati...
23. IPCA Laboratories Limited (2007). An improved process for the manufacture of 2-[(2,6-dichlorophenyl)amino]phenylacetoxyacetyl derivatives. (India Patent No. IN2004MU00640 A).
24. Dae Hwa Pharma. Co., Ltd. (2000). Process for preparing 2-[[2-[(2,6-dichlorophenyl)amino]phenyl]acetoxy]acetic acid. (Korea Patent No. KR2000026534 A). European Patent Office. https://worldwide.espacenet.com/patent/search/family/019554832/publicati...
25. K. J. Chul, N. S. Keon, C. J. Kun, C. B. Ra, C. H. Young. (1999). Preparation of aceclofenac haloethyl esters as antiinflammatories and aceclofenac intermediates (Patent No. WO9962865 A1). World Intellectual Property Organization. https://worldwide.espacenet.com/patent/search/family/019538371/publicati...
26. Patra, S. K., Mondal, P., Mandal, S., Ghosh, S., & Deb, S. (2015). Ultrasound-Promoted Synthesis of Aceclofenac. Journal of Scientific & Industrial Research, 74, 582-583. http://nopr.niscair.res.in/bitstream/123456789/32833/1/JSIR%2074%2810%29...
27. Zhang H. (2008). Method for preparing aceclofenac (China Patent No. CN101215243 A). European Patent Office. https://worldwide.espacenet.com/patent/search/family/039621763/publicati...
28. Qin B., Chen J., & Zhang Y. (2008). Synthesis of aceclofenac, Zhongguo Yiyao Gongye Zazhi, 39, 408-409.
29. Yang J., Gan B., Zhang Y., Cheng W., & Cao Z. (2006). Synthesis of aceclofenac, Zhongguo Yaoshi (Wuhan, China), 9, 1113-1114.
30. Ningbo Smart Pharmaceutical Co., Ltd. (2020). Method for industrial preparation of 2-[[2-[(2,6-dichlorophenyl)amino]phenyl]acetoxy]acetic acid (China Patent No. CN111848426 A). European Patent Office. https://worldwide.espacenet.com/patent/search/family/073001820/publicati...
31. Korea Biochem Pharm. Inc. (2020). Manufacturing method of aceclofenac and pharmaceutical preparations containing it (Korea Patent No. KR2020098992A). European Patent Office. https://worldwide.espacenet.com/patent/search/family/072235748/publicati...
32. Zhejiang University of Technology (2019). Preparation method of aceclofenac (China Patent No. CN110143891 A). European Patent Office. https://worldwide.espacenet.com/patent/search/family/067592402/publicati...
33. Amoli Organics Pvt. Ltd. (2015). An improved process for preparation of [2-(2,6- dichloroanilino)phenyl]acetoxy acetic acid (India Patent No. IN2013MU00480 A).
34. Bisel, P., Al‐Momani, L. A., & Müller, M. (2008). The tert-butyl group in chemistry and biology. Organic and Biomolecular Chemistry, 6(15), 2655. https://doi.org/10.1039/b800083b
https://doi.org/10.1039/b800083b