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Hydrogen pyrrolopyrrole derivatives useful as fatty acid synthase inhibitors

A technology for compounds and medicinal salts, applied in the field of hydrogen pyrrolopyrrole derivatives used as fatty acid synthase inhibitors, can solve the problems of affecting virus replication and the like

Inactive Publication Date: 2017-06-06
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Thus, changes in membrane lipid composition and / or distribution may affect viral replication

Method used

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  • Hydrogen pyrrolopyrrole derivatives useful as fatty acid synthase inhibitors
  • Hydrogen pyrrolopyrrole derivatives useful as fatty acid synthase inhibitors
  • Hydrogen pyrrolopyrrole derivatives useful as fatty acid synthase inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0243] 1-[5-(4-Isoquinolin-6-yl-benzoyl)-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl]-propan-1-one ("A1") Synthesis

[0244] .

[0245] 1.1 Dissolve tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (0,65 g; 3,06 mmol) in 20 ml of DCM. N-ethyldiisopropylamine for synthesis (1,56 ml; 9,19 mmol) was added and the mixture was cooled to 0°C. The 4-bromobenzoyl chloride (0,74 g; 3,37 mmol) used for the synthesis was now dissolved in 10 ml of DCM and added dropwise to the reaction, followed by stirring at RT for 14 hours. The reaction mixture was extracted with 50 ml of water. The organic layer was separated and washed with MgSO 4Dried, filtered, and reduced to dryness under vacuum to afford 1,10 g (90.9%) of 5-(4-bromo-benzoyl)-hexahydro-pyrrolo[3,4-c] as a light orange oil Pyrrole-2-carboxylic acid tert-butyl ester 1.

[0246] 1.2 Dissolve tert-butyl 5-(4-bromo-benzoyl)-hexahydro-pyrrolo[3,4-c]pyrrole-2-carboxylate (1,1 g; 2,78 mmol) in 15 ml HCl / isopropanol (5-6N), th...

Embodiment A

[0276] Example A: Injection Vials

[0277] A solution of 100 g of the active ingredient of formula I and 5 g of disodium hydrogen phosphate in 3 liters of double distilled water was adjusted to pH 6.5 using 2 N hydrochloric acid, sterile filtered, transferred to injection vials, lyophilized under sterile conditions and Seal under sterile conditions. Each injection vial contains 5 mg of active ingredient.

Embodiment B

[0278] Embodiment B: Suppository

[0279] A mixture of 20 g of active ingredient of formula I is melted with 100 g of soy lecithin and 1400 g of cocoa butter, poured into molds and allowed to cool. Each suppository contains 20 mg of active ingredient.

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Abstract

Compounds of formula (I), wherein R1, R2, R, X1, X2, X3, X4, n1, n2, n3 and n4 have the meanings indicated in claim 1, are inhibitors of fatty acid synthase and are especially useful in the treatment of Diseases such as cancer, cardiovascular disease, damage to the central nervous system, and different forms of inflammation.

Description

[0001] Technical Field of the Invention [0002] The present invention relates to novel hydropyrrolopyrrole derivatives which inhibit the activity of fatty acid synthase (FASN; also abbreviated as FAS), pharmaceutical compositions comprising them, processes for their preparation and their use in therapy for the treatment of cancer. [0003] Background of the invention [0004] Fatty acid synthase (FAS) is a key enzyme for endogenous lipogenesis and plays an important role in the regulation of key intermediates of lipid and carbohydrate cellular metabolism. FAS is highly expressed in tissues with high metabolic activity such as liver, adipose tissue and brain and there is good reason to believe that FAS inhibitors cause beneficial metabolic effects in peripheral tissues. In addition, inhibition of FAS in the hypothalamus may result in reduced food intake. The nonspecific, irreversible FAS inhibitors cerulenin and C-75 have been reported in the literature to decrease brain level...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/04A61K31/407A61P35/00
CPCA61K31/407A61K31/4725C07D487/04A61P25/00A61P29/00A61P35/00A61P35/02A61P43/00A61P9/00
Inventor W.施特勒C.察克拉基迪斯B.吕特纳D.温克F.乔德纳A.韦格纳
Owner MERCK PATENT GMBH
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