Simple Practical Preparations of Sufentanil from Cheap and Commercially Available 1-methyl-4-piperidone

References

1. Stanley T.H. Egan T.D. Van Aken H. Anesth. Analg. 2008 106 2 451 462 10.1213/ane.0b013e3181605add 18227300
   [Google Scholar]
2. Bird H.E. Huhn A.S. Dunn K.E. J. Addict. Med. 2023 17 5 503 508 10.1097/ADM.0000000000001185 37788600
   [Google Scholar]
3. Thompson J.P. Thompson D.F. Ann. Pharmacother. 2016 50 10 882 891 10.1177/1060028016659077 27413071
   [Google Scholar]
4. Prommer E. Thompson L. Patient Prefer. Adherence 2011 5 157 164 10.2147/PPA.S7665 21573046
   [Google Scholar]
5. Escobar Y. Mañas A. Juliá J. Gálvez R. Zaragozá F. Margarit C. López R. Casas A. Antón A. Cruz J.J. Clin. Transl. Oncol. 2013 15 7 526 534 10.1007/s12094‑012‑0981‑1 23263914
   [Google Scholar]
6. Kornick C.A. Santiago-Palma J. Moryl N. Payne R. Obbens E.A.M.T. Drug Saf. 2003 26 13 951 973 10.2165/00002018‑200326130‑00004 14583070
   [Google Scholar]
7. Janssen P.A. Niemegeers C.J. Dony J.G. Arzneimittelforschung 1963 13 502 507 13957426
   [Google Scholar]
8. Janssen P. Adriaan J. Joseph F. Patent US3141823A, 1964.
9. Janssen P. Jageneau A.H.M. Demoen P.J.A. van De Westeringh C. De Canniere J.H.M. Raeymaekers A.H.M. Wouters M. Sanczuk S. Hermans B.K.F. J. Med. Pharm. Chem. 1960 2 3 271 280 10.1021/jm50010a003 14406756
   [Google Scholar]
10. Gupta P.K. Ganesan K. Pande A. Malhotra R.C. J. Chem. Res. 2005 2005 7 452 453 10.3184/030823405774309078
    [Google Scholar]
11. Mićović I.V. Ivanović M.D. Vuckovic S.M. Prostran M.Š. Došen-Mićović L. Kiricojević V.D. Bioorg. Med. Chem. Lett. 2000 10 17 2011 2014 10.1016/S0960‑894X(00)00394‑2 10987438
    [Google Scholar]
12. Murashova U.A. Sadchikova N.P. Skalkina L.V. Smirnov S.K. Pharm. Chem. J. 2004 38 6 336 338 10.1023/B:PHAC.0000048149.69824.4d
    [Google Scholar]
13. Jeal W. Benfield P. Drugs 1997 53 1 109 138 10.2165/00003495‑199753010‑00011 9010652
    [Google Scholar]
14. Zheng L. Wu L.J. Anhui Yiyao 2016 20 576 578 10.3969/j.issn.1009‑6469.2016.03.052
    [Google Scholar]
15. Mićović I.V. Roglić G.M. Ivanović M.D. Došen-Mićović L. Kiricojević V.D. Popović J.B. J. Chem. Soc., Perkin Trans. 1 1996 1 16 2041 2050 10.1039/P19960002041
    [Google Scholar]
16. Van Daele P.G.H. De Bruyn M.F.L. Boey J.M. Sanczuk S. Agten J.T.M. Janssen P.A.J. Arzneimittelforschung 1976 26 8 1521 1531 10.1002/chin.197646236 12769
    [Google Scholar]
17. Fujita W. Gomes I. Devi L.A. Br. J. Pharmacol. 2015 172 2 375 387 10.1111/bph.12663 24571499
    [Google Scholar]
18. Shang Y. Filizola M. Eur. J. Pharmacol. 2015 763 Pt B 206 213 10.1016/j.ejphar.2015.05.012 25981301
    [Google Scholar]
19. Mores K.L. Cassell R.J. van Rijn R.M. Neuropharmacology 2019 152 15 21 10.1016/j.neuropharm.2018.11.010 30419245
    [Google Scholar]
20. Kabli N. Nguyen T. Balboni G. O’Dowd B.F. George S.R. Mol. Psychiatry 2014 19 9 986 994 10.1038/mp.2013.115 24061495
    [Google Scholar]
21. Faouzi A. Uprety R. Gomes I. Massaly N. Keresztes A.I. Le Rouzic V. Gupta A. Zhang T. Yoon H.J. Ansonoff M. Allaoa A. Pan Y.X. Pintar J. Morón J.A. Streicher J.M. Devi L.A. Majumdar S. J. Med. Chem. 2020 63 22 13618 13637 10.1021/acs.jmedchem.0c00901 33170687
    [Google Scholar]
22. Gupta A. Mulder J. Gomes I. Rozenfeld R. Bushlin I. Ong E. Lim M. Maillet E. Junek M. Cahill C.M. Harkany T. Devi L.A. Sci. Signal. 2010 3 131 ra54 ra60 10.1126/scisignal.2000807 20647592
    [Google Scholar]
23. Pierre F. Ugur M. Faivre F. Doridot S. Veinante P. Massotte D. Neuropharmacology 2019 152 30 41 10.1016/j.neuropharm.2019.03.009 30858104
    [Google Scholar]
24. Kreeger T.J. Arnemo J.M. Handbook of Wildlife Chemical Immobilization. Wyoming International Wildlife Veterinary Services Laramie 1996
    [Google Scholar]
25. Nakhaee S. Saeedi F. Mehrpour O. Heliyon 2023 9 12 e23083 10.1016/j.heliyon.2023.e23083 38144320
    [Google Scholar]
26. Ferrarezi W.P.P. Braga A.F.A. Ferreira V.B. Mendes S.Q. Brandão M.J.N. Braga F.S.S. Carvalho V.H. Braz. J. Anesthesiol. 2021 71 6 642 648 10.1016/j.bjane.2021.03.030 34411627
    [Google Scholar]
27. Palamar J.J. Cottler L.B. Goldberger B.A. Severtson S.G. Grundy D.J. Iwanicki J.L. Ciccarone D. Am. J. Drug Alcohol Abuse 2022 48 4 471 480 10.1080/00952990.2022.2081923 35704785
    [Google Scholar]
28. Pasternak G.W. Pan Y.X. Pharmacol. Rev. 2013 65 4 1257 1317 10.1124/pr.112.007138 24076545
    [Google Scholar]
29. Monk J.P. Beresford R. Ward A. Drugs 1988 36 3 286 313 10.2165/00003495‑198836030‑00003 2903821
    [Google Scholar]
30. Porela-Tiihonen S. Kokki H. Kokki M. Expert Opin. Pharmacother. 2020 21 12 1407 1418 10.1080/14656566.2020.1766025 32486875
    [Google Scholar]
31. Zhi M. Diao Y. Liu S. Huang Z. Su X. Geng S. Shen L. Sun J. Liu Y. Eur. J. Clin. Pharmacol. 2020 76 4 501 506 10.1007/s00228‑019‑02806‑x 31912188
    [Google Scholar]
32. Waara-Wolleat K.L. Hildebrand K.R. Stewart G.R. Pain Med. 2006 7 3 251 259 10.1111/j.1526‑4637.2006.00155.x 16712626
    [Google Scholar]
33. Alnemari A.M. Krafcik B.M. Mansour T.R. Gaudin D. World Neurosurg. 2017 106 509 528 10.1016/j.wneu.2017.07.009 28712906
    [Google Scholar]
34. Janssen P.A. Van Daele G.H.N Patent US4179569A, 1976.
35. Puthuparampil P.K. Eturi S.R. Carroll R. Patent WO2008005423A1, 2008. 2008
36. Walz A.J. Hsu F.L. Tetrahedron Lett. 2014 55 2 501 502 10.1016/j.tetlet.2013.11.058
    [Google Scholar]
37. Srimurugan S. Murugan K. Chen C. Chem. Pharm. Bull. (Tokyo) 2009 57 12 1421 1424 10.1248/cpb.57.1421 19952457
    [Google Scholar]
38. Killgore K. Mattew J. Patent US7208604B2, 2007.
39. Shin D.Y. Ryu J.S. Hyun S.S. Park H.J. Jeon R.O. Suh Y.G. Arch. Pharm. Res. 1999 22 4 398 400 10.1007/BF02979064 10489880
    [Google Scholar]
40. Kudzma L.V. Severnak S.A. Benvenga M.J. Ezell E.F. Ossipov M.H. Knight V.V. Rudo F.G. Spencer H.K. Spaulding T.C. J. Med. Chem. 1989 32 12 2534 2542 10.1021/jm00132a007 2585442
    [Google Scholar]
41. Esipova T.V. Borisenko A.A. Terent’ev P.B. Grishina G.V. Herzshuh R. Russ. J. Org. Chem. 2006 42 5 742 747 10.1134/S1070428006050162
    [Google Scholar]
42. Nakatsubo F. Cocuzza A.J. Keeley D.E. Kishi Y. J. Am. Chem. Soc. 1977 99 14 4835 4836 10.1021/ja00456a056 874235
    [Google Scholar]
43. Vatele J.M. Tetrahedron Lett. 1984 25 52 5997 6000 10.1016/S0040‑4039(01)81742‑1
    [Google Scholar]
44. Manoharan T.S. Madyastha K.M. Singh B.B. Bhatnagar S.P. Weiss U. Synthesis 1983 1983 10 809 812 10.1055/s‑1983‑30523
    [Google Scholar]
45. Koldobskii A.B. Morozova S.M. Shilova O.S. Dankov Y.V. Moiseev S.K. J. Fluor. Chem. 2024 273 110236 10.1016/j.jfluchem.2023.110236
    [Google Scholar]
46. Braga F.C. Ramos T.O. Brocksom T.J. de Oliveira K.T. Org. Lett. 2022 24 45 8331 8336 10.1021/acs.orglett.2c03338 36346151
    [Google Scholar]
47. Ghaffarzadeh M. Joghan S.S. Faraji F. Tetrahedron Lett. 2012 53 2 203 206 10.1016/j.tetlet.2011.11.018
    [Google Scholar]
48. Brandsma L. Vasilevsky S.F. Verkuijsse H.D. Application of transition metal catalysts in organic synthesis. New York Springer-Verlag 2012
    [Google Scholar]
49. Stokes B.J. Opra S.M. Sigman M.S. J. Am. Chem. Soc. 2012 134 28 11408 11411 10.1021/ja305403s 22742056
    [Google Scholar]
50. Vardanyan R. Vijay G. Nichol G.S. Liu L. Kumarasinghe I. Davis P. Vanderah T. Porreca F. Lai J. Hruby V.J. Bioorg. Med. Chem. 2009 17 14 5044 5053 10.1016/j.bmc.2009.05.065 19540763
    [Google Scholar]