Cloricromen

Cloricromen
Clinical data
ATC code	B01AC02 (WHO) ;
Identifiers
	IUPAC name Ethyl 2-(8-chloro-3-(2-(diethylamino)ethyl)-4-methyl-2-oxo-2H-chromen-7-yloxy)acetate;
CAS Number	68206-94-0;
PubChem CID	68876;
ChemSpider	62108 ;
UNII	B9454PE93C;
KEGG	D07139 ;
ChEMBL	ChEMBL255066 ;
CompTox Dashboard (EPA)	DTXSID2048373 ;
ECHA InfoCard	100.164.003
Chemical and physical data
Formula	C20H26ClNO5
Molar mass	395.88 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(OCC)COc2ccc\1c(OC(=O)/C(=C/1C)CCN(CC)CC)c2Cl;
	InChI InChI=1S/C20H26ClNO5/c1-5-22(6-2)11-10-15-13(4)14-8-9-16(26-12-17(23)25-7-3)18(21)19(14)27-20(15)24/h8-9H,5-7,10-12H2,1-4H3 ; Key:GYNNRVJJLAVVTQ-UHFFFAOYSA-N ;
	(verify)

Cloricromen is a platelet aggregation inhibitor.^[1] Coronary vasodilator.

Synthesis[edit]

Base catalyzed alkylation of Ethyl Acetoacetate [141-97-9] (1) with 2-Chlorotriethylamine [100-35-6] (2) gives ethyl 2-(2-diethylaminoethyl)acetoacetate [23999-02-2] (3). Disulfonation of resorcinol [108-46-3] (4) with 96% sulfuric acid gives 4,6-dihydroxybenzene-1,3-disulfonic Acid [17724-11-7] (5). This is reacted with potassium chlorate [3811-04-9] in acid and alkalized to give 5-Chloro-4,6-dihydroxybenzene-1,3-disulfonic acid, PC20077643 (6). Hydrolysis of the sulfonate groups in dilute acid occurs to give 2-chlororesorcinol [6201-65-6] (7). The acid catalyzed condensation between (3) and (7) led to 8-chloro-3-[2-(diethylamino)ethyl]-7-hydroxy-4-methylchromen-2-one, PC20144545 [70665-54-2] (8). Ether formation with ethyl bromoacetate [105-36-2] (9) completed the synthesis of Carbocromen (10).

References[edit]

^ Orefice G, Grasso A, Fazio N, Del Vecchio G, Volpe G, Coppola M, D'Alessio A, Carrieri PB (1994). "No effect of cloricromen on some coagulation parameters in patients with ischaemic cerebrovascular disease". The Journal of International Medical Research. 22 (5): 287–91. doi:10.1177/030006059402200506. PMID 7867874. S2CID 36081514.
^ Castaer, J.; Hillier, K.; Serradell, MN; Blancafort, P.; AD-6. Drugs Fut 1979, 4, 10, 701.
^ BE871315 idem Francesco Della Valle, U.S. patent 4,452,811 (1984 to Fidia S.P.A.).
^ Weizmann, Ch.; Bergmann, E.; Sulzbacher, M. (1950). "THE USE, FOR CONDENSATION REACTIONS, OF POTASSIUM HYDROXIDE IN SOLVENTS OF THE ACETAL TYPE". The Journal of Organic Chemistry. 15 (5): 918–929. doi:10.1021/jo01151a002.
^ Francesco D. Valle & Aurelio Romeo, U.S. patent 4,704,469 (1987 to Fidia Farmaceutici SpA).
^ Wanzlick, H., Mohrmann, S. (August 1963). "Notiz über einen neuen Weg zum 2‐Chlor‐resorcin". Chemische Berichte. 96 (8): 2257–2258. doi:10.1002/cber.19630960843.

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[pmid7867874-1] Orefice G, Grasso A, Fazio N, Del Vecchio G, Volpe G, Coppola M, D'Alessio A, Carrieri PB (1994). "No effect of cloricromen on some coagulation parameters in patients with ischaemic cerebrovascular disease". The Journal of International Medical Research. 22 (5): 287–91. doi:10.1177/030006059402200506. PMID 7867874. S2CID 36081514.

[2] Castaer, J.; Hillier, K.; Serradell, MN; Blancafort, P.; AD-6. Drugs Fut 1979, 4, 10, 701.

[3] BE871315 idem Francesco Della Valle, U.S. patent 4,452,811 (1984 to Fidia S.P.A.).

[4] Weizmann, Ch.; Bergmann, E.; Sulzbacher, M. (1950). "THE USE, FOR CONDENSATION REACTIONS, OF POTASSIUM HYDROXIDE IN SOLVENTS OF THE ACETAL TYPE". The Journal of Organic Chemistry. 15 (5): 918–929. doi:10.1021/jo01151a002.

[5] Francesco D. Valle & Aurelio Romeo, U.S. patent 4,704,469 (1987 to Fidia Farmaceutici SpA).

[6] Wanzlick, H., Mohrmann, S. (August 1963). "Notiz über einen neuen Weg zum 2‐Chlor‐resorcin". Chemische Berichte. 96 (8): 2257–2258. doi:10.1002/cber.19630960843.

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Synthesis[edit]

See also[edit]

References[edit]