Sibopirdine

Sibopirdine
Clinical data
ATC code	none;
Legal status
Legal status	In general: unscheduled;
Pharmacokinetic data
Bioavailability	sus
Metabolism	sus
Excretion	sus
Identifiers
	IUPAC name 5,5-bis(4-pyridylmethyl)-5H-cyclopenta[2,1-b:3,4-b']dipyridine;
CAS Number	139781-09-2 ; anhydrous: 122955-18-4 ;
PubChem CID	9929210;
ChemSpider	169416 ;
UNII	RAG2185DR1; anhydrous: 7IKM67CSEQ ;
KEGG	D05833 ;
CompTox Dashboard (EPA)	DTXSID60930596 ;
Chemical and physical data
Formula	C23H18N4
Molar mass	350.425 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES c5cnccc5CC1(Cc3ccncc3)c2cccnc2-c4c1cccn4;
	InChI InChI=1S/C23H18N4/c1-3-19-21(26-9-1)22-20(4-2-10-27-22)23(19,15-17-5-11-24-12-6-17)16-18-7-13-25-14-8-18/h1-14H,15-16H2 ; Key:FJYRSJDIZKTXKB-UHFFFAOYSA-N ;
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Sibopirdine, also known as EXP921, is a nootropic drug.^[1]

Synthesis

Patent:^[2]

4,5-Diazafluoren-9-one [50890-67-0] (1) is condensed with 4 molar equivalents of 4-picoline [108-89-4] (2) in the presence of 2 equivalents of acetic anhydride and acetic acid. The intermediate from this step may originally be a tertiary alcohol which then dehydrates under the reaction conditions to give [150896-71-2] (3). The olefin can then be reduced either by catalytic hydrogenation over 5% Pd/C or by sodium borohydride in alcohol to give [150896-72-3] (4). Alkylation with 4-picolyl chloride [10445-91-7] (5) in the presence of sodium hydroxide completed the synthesis of sibopirdine (6).

References

↑ Wong YN, Quon CY, Holm KA, Burcham DL, Frey NL, Huang SM, Lam GN (February 1996). "Pharmacokinetics and metabolism of EXP921, a novel cognitive enhancer, in rats". Drug Metabolism and Disposition. 24 (2): 172–9. doi:10.1016/S0090-9556(25)07294-0. PMID 8742228.
↑ James H. Jensen, Timothy D. Costello, Leon De Brabander, Jr., Matthew E. Voss, U.S. patent 5,272,269 (1993 to DuPont Merck Pharmaceutical Company).

[1] Wong YN, Quon CY, Holm KA, Burcham DL, Frey NL, Huang SM, Lam GN (February 1996). "Pharmacokinetics and metabolism of EXP921, a novel cognitive enhancer, in rats". Drug Metabolism and Disposition. 24 (2): 172–9. doi:10.1016/S0090-9556(25)07294-0. PMID 8742228.

[2] James H. Jensen, Timothy D. Costello, Leon De Brabander, Jr., Matthew E. Voss, U.S. patent 5,272,269 (1993 to DuPont Merck Pharmaceutical Company).

[1]

[2]

Synthesis

See also

References