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Acyclic Sulfamide Derivatives

a technology of acyclic sulfamide and derivatives, applied in the field of acyclic sulfamide derivatives, can solve problems such as increase in levels, and achieve the effect of reducing cumulative relative weight gain and body weigh

Inactive Publication Date: 2010-02-25
FUNDACION IMABIS INST MEDITERRANEO PARA EL AVANCE DE LA BIOTECHA Y LA INVESTIGACION SANITARIA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0035] According to a fifth aspect, the present invention is directed to the cosmetic use of a compound of formula (I) for reducing subcutaneous fat.

Problems solved by technology

The increase of the levels of this composition is directly related to the risk of coronary disease.

Method used

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Examples

Experimental program
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Effect test

example 1

Preparation of N-(cis-9-octadecenyl)sulfamide (1), also known as N-oleylsulfamide

[0133] To a stirred solution of 0.20 g of sulfamide (2.1 mmol) in 20 ml of H2O under reflux it is added dropwise 0.1 ml (2.1 mmol) of N-oleylamine in 10 ml of EtOH for 30 minutes. The reaction mixture is stirred and refluxed for 6 hours. Then the solvent is evaporated and the white solid is purified in a chromatography column, using CH2Cl2:MeOH / NH3 9.4:0.6 as eluyent; 0.52 g of white solid are obtained. Yield 72%; mp=68-70 C;

[0134]1H NMR (300 MHz, CDCl3): 5.32 (m, 2H); 4.59 (br s, 2H); 4.38 (br s, 1H); 3.09 (q, J=7.0 Hz, 2H); 1.97 (m, 4H); 1.55 (m, 2H); 1.24 (m, 22H); 0.85 (t, J=6.7 Hz, 3H).

[0135]13C NMR (75 MHz, CDCl3): 129.9; 129.7; 43.6; 31.8; 29.7-26.6; 27.1; 27.2; 22.6; 14.1.

[0136] MS (ES+) [M+H]+347 (100%). Anal. (C18H38N2SO2, 346.57): C, H, N, S.

example 2

Preparation of N-octadecylsulfamide (2)

[0137] 0.270 g, (1.0 mmol) of N-octadecylamine and 0.100 g (1.0 mmol) of sulfamide in 50 ml of THF (50 mL) are stirred and refluxed for 51 h. The solvent is evaporated and the crude is purified in a chromatography column, using CH2Cl2:MeOH / NH3 9:1 as eluyent. 0.06 g of white solid are obtained. Yield 18%; mp=105-107° C.;

[0138]1H NMR (400 MHz, DMSO-d6): 6.39 (br s, 2H); 6.33 (br s, 1H); 2.82 (m, 2H); 1.42 (m, 2H); 1.21 (bm, 30H); 0.83 (t, J=6.8 Hz, 3H).

[0139]13C NMR (100 MHz, DMSO-d6): 42.7; 31.4; 29.1; 26.5; 22.2; 14.1;

[0140] MS (ES+) [M+H]+349 (100%). Anal. (C18H40N2SO2, 348.64): C, H, N, S.

example 3

Preparation of N-hexadecylsulfamide (3)

[0141] The title compound was prepared following the procedure previously described in Example 1, using 0.5 g (2.0 mmol) of N-hexadecylamine and 0.195 g (2.0 mmol) of sulfamide as starting reagent. 0.087 g of a white solid were obtained. Yield 16%; m.p. 102-104° C.

[0142]1H-NMR (500 MHz, DMSO-d6) δ: 2.83 (c, 2H, |J|=6.8 Hz CH2NHSO2); 1.43 (1, 2H, |J|=6.8 Hz, CH2—CH2NHSO2); 1.23 (s, 20H, —CH2—); 0.85 (t, 3H, |J|=6.8 Hz, CH2—CH3).

[0143]13C-NMR (125 MHz, DMSO-d6) δ: 42.5 (CH2NH); 31.3 (CH2—CH2NH); 29.0-28.7 (—CH2—); 26.4 (CH2—CH2—CH2NH); 22.1 (CH2—CH3); 13.9 (CH2—CH3).

[0144] Anal (C16H36N2SO2) % theor. (% found): C, 59.95 (59.68); H, 11.32 (11.04); N, 8.74 (8.65); S, 10.00 (9.91).

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Abstract

The present invention is related to acyclic sulphamide derivatives of formula (I), wherein R1 and R2 may be the same or different, when R1 and R2 are different, R1 is a linear C12-C20 alkyl group or a linear C12-C20 alkenyl group comprising 1, 2, 3 or 4 double bonds; and R2 is a hydrogen atom or a C1-C4 alkyl group, or when R1 and R2 are the same, R1 and R2 are a linear C14-C20 alkyl group or a linear C14-C20 alkenyl group with 1, 2, 3 or 4 double bonds, and pharmaceutically acceptable salts, solvates and hydrates thereof, useful for the manufacture of a medicament for satiety induction and ingestion control, corporal fat modulation and lipidic metabolism regulation and for the manufacture of a medicament for the treatment or prevention of diabetes and cardiovascular diseases. The acyclic sulphamide derivatives are also useful for cosmetic use for reducing subcutaneous fat.

Description

FIELD OF THE INVENTION [0001] The present invention is related to acyclic sulfamide derivatives, useful for the treatment of obesity and feeding disorders. BACKGROUND OF THE INVENTION [0002] There is an increasing need for the provision of active compounds for the treatment of obesity and feeding disorders. In recent years there has been a substantial research effort in finding new pharmacological targets for the treatment of these conditions. [0003] One of the most promising targets discovered are peroxisome proliferator activated receptors (PPAR) which are a superfamily belonging to the nuclear hormone receptors, which are ligand activated transcription factors that play a key role in the regulation of the metabolism of lipids and carbohydrates. In addition, it has been discovered that PPAR's also play a key role in satiety induction and ingestion control and corporal fat modulation, as well as in the treatment and prevention of diabetes and cardiovascular diseases. [0004] Three s...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): A61K31/16C07C307/06A61P3/10A61P9/00
CPCA61K8/466C07C307/06A61Q19/06A61P3/10A61P3/04A61P3/06A61P43/00A61P9/00
Inventor RODRIGUEZ DE FONSECA, FERNANDO ANTONIOMACIAS GONZALEZ, MANUELPAVON MORON, JAVIERGOYA-LAZA, MARIA PILARPAEZ PROSPER, JUAN ANTONIOCANO RAMOS, CAROLINA
Owner FUNDACION IMABIS INST MEDITERRANEO PARA EL AVANCE DE LA BIOTECHA Y LA INVESTIGACION SANITARIA
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