Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Hydropyrrolopyrrole derivatives for use as fatty acid synthase inhibitors

A technology of pyrrole and compound is applied in the field of hydrogen pyrrolopyrrole derivatives used as fatty acid synthase inhibitors, and can solve the problems of affecting virus replication and the like

Inactive Publication Date: 2015-05-20
MERCK PATENT GMBH
View PDF17 Cites 0 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Hydropyrrolopyrrole derivatives for use as fatty acid synthase inhibitors
  • Hydropyrrolopyrrole derivatives for use as fatty acid synthase inhibitors
  • Hydropyrrolopyrrole derivatives for use as fatty acid synthase inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0241] 1-[5-(4-Isoquinolin-6-yl-benzoyl)-hexahydro-pyrrolo[3,4-c]pyrrol-2-yl]-propan-1-one ("A1") Synthesis

[0242] .

[0243] 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 tert-butyl pyrrole-2-carboxylate 1 .

[0244] 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), then stirr...

Embodiment A

[0274] Example A: Injection Vials

[0275] 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

[0276] Embodiment B: Suppository

[0277] 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.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

PropertyMeasurementUnit
particle sizeaaaaaaaaaa
wavelengthaaaaaaaaaa
Login to View More

Abstract

Compounds of the formula (I) in which R1, R2, R, X1, X2, X3, X4, n1, n2, n3 and n4 have the meanings indicated in Claim 1, are inhibitors of Tankyrase, 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

[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. Background of the invention [0003] 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 levels of ore...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com