NGB 2904 NGB 2849: Two highly selective dopamine D3 receptor antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 19, 1998, Pages 2715-2718

  Yuan, Jun ^a   Chen, Xi ^a   Brodbeck, Robbin ^a   Primus, Renee ^a   Braun, Julia ^a   Wasley, Jan W F ^a   Thurkauf, Andrew ^a  

^a NEUROGEN CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DOPAMINE 3 RECEPTOR; DOPAMINE 3 RECEPTOR BLOCKING AGENT; HALOPERIDOL; N [4 [4 (2,3 DICHLOROPHENYL) 1 PIPERAZINYL]BUTYL] 2 BIPHENYLENYLCARBOXAMIDE; N [4 [4 (2,3 DICHLOROPHENYL) 1 PIPERAZINYL]BUTYL] 3 FLUORENYLCARBOXAMIDE; QUINPIROLE; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CHO CELL; DOPAMINERGIC SYSTEM; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; NEUROPHARMACOLOGY; NONHUMAN; RAT; SCHIZOPHRENIA;

ANIMALS; CHO CELLS; CRICETINAE; DOPAMINE ANTAGONISTS; FLUORENES; HUMANS; KINETICS; PIPERAZINES; RATS; RECEPTORS, DOPAMINE D2; RECEPTORS, DOPAMINE D3; TRANSFECTION;

ANIMALIA;

EID: 0032491245     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00469-7     Document Type: Article

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10. 10. A mixture of phosphorus pentoxide (140 g) and triethylamine hydroichloride (67 g) was melted at 200 °C under a nitrogen atmosphere with mechanical stirring. To this was added 20 g of 2,3-dichloroaniline and diethanolamine (13 g) and heating continued for an additional 3 h. After cooling to 100 °C the mixture was poured into water and the pH adjusted to 7 with the addition of NaOH. The solid material was filtered, suspended in 10% HCl and washed with hexane to remove unreacted aniline. The aqueous was basified with 10 N NaOH solution and extracted with chloroform. The organic layer was dried, concentrated and purified by chromatography to provide 2,3-dichlorophenylpiperazine (5.9 g, 21%). The fumarate salt was prepared in methanol and crystallized from ethanol, mp 213-215 °C.
11. 6) hydrobromide 8.60 (m, 1H), 8.08 (s, 1H), 7.95 (dd, J = 7, 2 Hz, 2H), 7.95 (m, 1H), 7.90 (d, J = 8 Hz, 1H), 7.60 (d, J = 7 Hz, 1H), 7.32-7.42 (m, 3H), 7.19 (dd, J = 7. 2 Hz, 2H), 4.0 (s, 2H), 3.58 (m, 2H), 3.3 (m, 2H), 3.2 (m, 6H), 1.8 (m, 2H), 1.6 (m, 2H). Anal. C, H, N calc. 62.95, 5.45, 6.88; found 63.19, 5.43, 6.69.
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