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Piperazine derivatives as FASN inhibitors

A compound and mixture technology, applied in anti-inflammatory agents, suppository delivery, drug combination, etc., can solve problems such as weakening HCV replication

Inactive Publication Date: 2015-10-28
MERCK PATENT GMBH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Based on their pharmacological effects, these agents may attenuate HCV replication through disruption of lipid rafts

Method used

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  • Piperazine derivatives as FASN inhibitors
  • Piperazine derivatives as FASN inhibitors
  • Piperazine derivatives as FASN inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0206] 1-[4-(4-Isoquinolin-6-yl-benzoyl)-piperazin-1-yl]-propan-1-one ("A1")

[0207]

[0208] 1.1 Dissolve tert-butyl-1-piperazinecarboxylate (0.5 g; 2.69 mmol) in 10 ml of dichloromethane (DCM). N-ethyldiisopropylamine (1.37 ml; 8.06 mmol) for synthesis was added, and the mixture was cooled to 0°C. Now, the 4-bromobenzoyl chloride (0.66 g; 2.95 mmol) used for the synthesis was dissolved in 10 ml DCM and added dropwise to the reaction, followed by stirring overnight at room temperature. On LC-MS, the reaction was complete. The reaction mixture was extracted with 50 mL of water. The organic layer was washed with MgSO 4Drying, filtering off, and then reducing to dryness under vacuum afforded 1,0 g (100%) of tert-butyl 4-(4-bromo-benzoyl)-piperazine-1-carboxylate 1 as a beige solid.

[0209] 1.2 Dissolve tert-butyl 4-(4-bromo-benzoyl)-piperazine-1-carboxylate 1 (0.5 g; 1.35 mmol) in 15 ml HCl / isopropanol (5-6N), and then °C and stirred for 2 hours. The reaction mixture ...

Embodiment A

[0222] Example A: Injection vial

[0223] A solution of 100 g of the active ingredient of formula I and 5 g of disodium hydrogen phosphate in 3 l of double distilled water was adjusted to pH 6.5 using 2 N hydrochloric acid, sterile filtered, transferred into injection vials and lyophilized under sterile conditions , and sealed under sterile conditions. Each injection vial contains 5 mg of active ingredient.

Embodiment B

[0224] Embodiment B: Suppository

[0225] A mixture of 20 g of active ingredient of formula I and 100 g of soy lecithin and 1400 g of cocoa butter is melted, poured into molds and allowed to cool. Each suppository contains 20 mg of active ingredient.

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Abstract

Compounds of the formula (I), in which R, X1, X2, X3, X4, R1, R2 and q have the meanings indicated in Claim 1, are inhibitors of fatty acid synthase, and can be employed, inter alia, for the treatment of diseases such as cancer, cardiovascular diseases, central nervous system injury and different forms of inflammation.

Description

technical field [0001] The present invention relates to novel piperazine 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. Background technique [0002] Fatty acid synthase (FAS) is an enzyme critical 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. Additionally, inhibition of FAS in the hypothalamus may result in reduced food intake. The nonspecific and irreversible FAS inhibitors cercyanin and C-75 have been reported in the literature to reduce brain levels of orexin-promoting neuropeptides and...

Claims

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Application Information

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IPC IPC(8): C07D217/02A61K31/4725A61K31/496C07D217/24A61P9/00A61P25/00A61P35/00
CPCC07D217/24A61K9/0014A61K9/0019A61K9/02C07D217/02C07D217/08A61K31/496A61P25/00A61P25/28A61P29/00A61P35/00A61P35/02A61P9/00Y02A50/30
Inventor W.施特勒C.察克拉基迪斯M.弗里泽-哈米姆B.罗伊特纳D.维恩克
Owner MERCK PATENT GMBH
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