The condensation between
ethyl cyanoacetate (1) and
acetone gives ethylisopropylidenecyanoacetate [759-58-0] (2). This product is reacted with N-butylcyanoacetamide [39581-21-0] (3) in sodium methoxide solution to give N-butyl-2,4-dicyano-3,3-dimethylglutarimide,
CID:10681941 (4). The
glutarimide is cyclized with phosphoric acid to yield 3-butyl-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetraone,
https://pubchem.ncbi.nlm.nih.gov/compound/10825633 CID:10825633 (5).
^
abHolland RL, Wesnes K, Dietrich B (1994). "Single dose human pharmacology of umespirone". European Journal of Clinical Pharmacology. 46 (5): 461–8.
doi:
10.1007/bf00191912.
PMID7957544.
S2CID12117650.
^
abBarnes NM, Costall B, Domeney AM, et al. (September 1991). "The effects of umespirone as a potential anxiolytic and antipsychotic agent". Pharmacology Biochemistry and Behavior. 40 (1): 89–96.
doi:
10.1016/0091-3057(91)90326-W.
PMID1685786.
S2CID9762359.
^Ruhland M, Krähling H, Fuchs A, Schön U (November 1988). "KC 9172 (free base of KC 7218)--an antipsychotic/anxiolytic compound. I. Antipsychotic and anxiolytic activity in comparison with chlorpromazine, clozapine, diazepam and buspirone". Pharmacopsychiatry. 21 (6): 396–8.
doi:
10.1055/s-2007-1017024.
PMID2907649.
S2CID260241523.
^Krähling H, Fuchs A, Ruhland M, Schön U, Mol F, Tulp M (November 1988). "KC 9172 (free base of KC 7218)--an antipsychotic/anxiolytic compound. II. Discrimination from typical neuroleptics and benzodiazepine-like minor tranquilizers". Pharmacopsychiatry. 21 (6): 399–401.
doi:
10.1055/s-2007-1017025.
PMID2907650.
S2CID260241655.
^
abSchmidt WJ, Krähling H, Ruhland M (1991). "Antagonism of AP-5-induced sniffing stereotypy links umespirone to atypical antipsychotics". Life Sciences. 48 (6): 499–505.
doi:
10.1016/0024-3205(91)90464-M.
PMID1671523.
^
abAhlenius S, Wijkström A (November 1992). "Mixed agonist-antagonist properties of umespirone at neostriatal dopamine receptors in relation to its behavioral effects in the rat". European Journal of Pharmacology. 222 (1): 69–74.
doi:
10.1016/0014-2999(92)90464-F.
PMID1361441.
The condensation between
ethyl cyanoacetate (1) and
acetone gives ethylisopropylidenecyanoacetate [759-58-0] (2). This product is reacted with N-butylcyanoacetamide [39581-21-0] (3) in sodium methoxide solution to give N-butyl-2,4-dicyano-3,3-dimethylglutarimide,
CID:10681941 (4). The
glutarimide is cyclized with phosphoric acid to yield 3-butyl-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetraone,
https://pubchem.ncbi.nlm.nih.gov/compound/10825633 CID:10825633 (5).
^
abHolland RL, Wesnes K, Dietrich B (1994). "Single dose human pharmacology of umespirone". European Journal of Clinical Pharmacology. 46 (5): 461–8.
doi:
10.1007/bf00191912.
PMID7957544.
S2CID12117650.
^
abBarnes NM, Costall B, Domeney AM, et al. (September 1991). "The effects of umespirone as a potential anxiolytic and antipsychotic agent". Pharmacology Biochemistry and Behavior. 40 (1): 89–96.
doi:
10.1016/0091-3057(91)90326-W.
PMID1685786.
S2CID9762359.
^Ruhland M, Krähling H, Fuchs A, Schön U (November 1988). "KC 9172 (free base of KC 7218)--an antipsychotic/anxiolytic compound. I. Antipsychotic and anxiolytic activity in comparison with chlorpromazine, clozapine, diazepam and buspirone". Pharmacopsychiatry. 21 (6): 396–8.
doi:
10.1055/s-2007-1017024.
PMID2907649.
S2CID260241523.
^Krähling H, Fuchs A, Ruhland M, Schön U, Mol F, Tulp M (November 1988). "KC 9172 (free base of KC 7218)--an antipsychotic/anxiolytic compound. II. Discrimination from typical neuroleptics and benzodiazepine-like minor tranquilizers". Pharmacopsychiatry. 21 (6): 399–401.
doi:
10.1055/s-2007-1017025.
PMID2907650.
S2CID260241655.
^
abSchmidt WJ, Krähling H, Ruhland M (1991). "Antagonism of AP-5-induced sniffing stereotypy links umespirone to atypical antipsychotics". Life Sciences. 48 (6): 499–505.
doi:
10.1016/0024-3205(91)90464-M.
PMID1671523.
^
abAhlenius S, Wijkström A (November 1992). "Mixed agonist-antagonist properties of umespirone at neostriatal dopamine receptors in relation to its behavioral effects in the rat". European Journal of Pharmacology. 222 (1): 69–74.
doi:
10.1016/0014-2999(92)90464-F.
PMID1361441.