Lenperone was never approved by the FDA for use in humans in the United States,[3] but prior to 1989 it was approved for use in veterinary medicine for sedation.[4][5][6]
Synthesis
The alkylation between 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane [3308-94-9] (1) and 4-(4-fluorobenzoyl)piperidine [56346-57-7] (2) gives 2-(p-fluorophenyl)-2-{3-[4-(p-fluorobenzoyl)piperidino]propyl}-1,3-dioxolane,
CID:20318874 (3). Deprotection of the ketal function completes the synthesis of lenperone (4).
^Booth NJ (1982). "Psychotropic Agents". In Booth NH, McDonald LE (ed.). Veterinary Pharmacology and Therapeutics (5th ed.). Ames, Iowa: Iowa State University Press. pp. 321–345.
^FDA Veterinarian. U.S. Department of Health and Human Services, Public Health Service, Food and Drug Administration, Center for Veterinary Medicine. 1988. The firm requested withdrawal of approval because the products are no longer being marketed. Effective date: July 13, 1989
^Duncan RL, Helsley GC, Welstead WJ, DaVanzo JP, Funderburk WH, Lunsford CD (January 1970). "Aroylpiperidines and pyrrolidines. A new class of potent central nervous system depressants". Journal of Medicinal Chemistry. 13 (1): 1–6.
doi:
10.1021/jm00295a001.
PMID5460893.
^CN 107011133, Yanbiao K, Jie L, issued 2017, assigned to University of Science and Technology of China USTC.
^Liu J, Hu KF, Qu JP, Kang YB (October 2017). "Organopromoted Selectivity-Switchable Synthesis of Polyketones". Organic Letters. 19 (20): 5593–5596.
doi:
10.1021/acs.orglett.7b02731.
PMID28981291.
Lenperone was never approved by the FDA for use in humans in the United States,[3] but prior to 1989 it was approved for use in veterinary medicine for sedation.[4][5][6]
Synthesis
The alkylation between 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane [3308-94-9] (1) and 4-(4-fluorobenzoyl)piperidine [56346-57-7] (2) gives 2-(p-fluorophenyl)-2-{3-[4-(p-fluorobenzoyl)piperidino]propyl}-1,3-dioxolane,
CID:20318874 (3). Deprotection of the ketal function completes the synthesis of lenperone (4).
^Booth NJ (1982). "Psychotropic Agents". In Booth NH, McDonald LE (ed.). Veterinary Pharmacology and Therapeutics (5th ed.). Ames, Iowa: Iowa State University Press. pp. 321–345.
^FDA Veterinarian. U.S. Department of Health and Human Services, Public Health Service, Food and Drug Administration, Center for Veterinary Medicine. 1988. The firm requested withdrawal of approval because the products are no longer being marketed. Effective date: July 13, 1989
^Duncan RL, Helsley GC, Welstead WJ, DaVanzo JP, Funderburk WH, Lunsford CD (January 1970). "Aroylpiperidines and pyrrolidines. A new class of potent central nervous system depressants". Journal of Medicinal Chemistry. 13 (1): 1–6.
doi:
10.1021/jm00295a001.
PMID5460893.
^CN 107011133, Yanbiao K, Jie L, issued 2017, assigned to University of Science and Technology of China USTC.
^Liu J, Hu KF, Qu JP, Kang YB (October 2017). "Organopromoted Selectivity-Switchable Synthesis of Polyketones". Organic Letters. 19 (20): 5593–5596.
doi:
10.1021/acs.orglett.7b02731.
PMID28981291.