NNC 38-1049

NNC 38-1049 is a histamine antagonist selective for the H3 subtype. It has anorectic effects in animal studies and is being researched as a potential treatment for obesity.[1][2]

NNC 38-1049
Names
Preferred IUPAC name
1-(4-Chlorophenyl)-4-(4-cyclopentylpiperazin-1-yl)butane-1,4-dione
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
InChI
  • InChI=1S/C19H25ClN2O2/c20-16-7-5-15(6-8-16)18(23)9-10-19(24)22-13-11-21(12-14-22)17-3-1-2-4-17/h5-8,17H,1-4,9-14H2 Y
    Key: VPARRMQGLNFBBR-UHFFFAOYSA-N Y
  • InChI=1/C19H25ClN2O2/c20-16-7-5-15(6-8-16)18(23)9-10-19(24)22-13-11-21(12-14-22)17-3-1-2-4-17/h5-8,17H,1-4,9-14H2
    Key: VPARRMQGLNFBBR-UHFFFAOYAT
SMILES
  • Clc1ccc(cc1)C(=O)CCC(=O)N3CCN(C2CCCC2)CC3
Properties
Chemical formula
 C19H25ClN2O2
Molar mass 348.866 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Synthesis
Patent (Ex 188):[3] Precursor:[4]

The alkylation reaction between 1-cyclopentylpiperazine [21043-40-3] (1) and 3-(4-Chlorobenzoyl)Propionic Acid [3984-34-7] (3) was catalyzed by Hydroxybenzotriazole and 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide.

References
  1. Malmlöf K, Zaragoza F, Golozoubova V, et al. (December 2005). "Influence of a selective histamine H3 receptor antagonist on hypothalamic neural activity, food intake and body weight". Int J Obes (Lond). 29 (12): 1402–12. doi:10.1038/sj.ijo.0803036. PMID 16151415.
  2. Malmlöf K, Golozoubova V, Peschke B, Wulff BS, Refsgaard HH, Johansen PB, Cremers T, Rimvall K (Dec 2006). "Increase of neuronal histamine in obese rats is associated with decreases in body weight and plasma triglycerides". Obesity (Silver Spring). 14 (12): 2154–62. doi:10.1038/oby.2006.252. PMID 17189541.
  3. Florencio Zaragoza DÖRWALD, Knud Erik Andersen, & Jan Lindy Sorensen, WO 2003004480 (Novo Nordisk AS).
  4. Soichi Hashimoto, JPS 61158973A 1986 to Koei Chemical Co Ltd.


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