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1628260-79-6,MFCD31544330
Catalog No.:AA001TDD

1628260-79-6 | GLPG1690

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1mg
98+%
in stock  
$15.00   $11.00
- +
5mg
98+%
in stock  
$37.00   $26.00
- +
25mg
98+%
in stock  
$91.00   $64.00
- +
50mg
98+%
in stock  
$138.00   $96.00
- +
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA001TDD
Chemical Name:
GLPG1690
CAS Number:
1628260-79-6
Molecular Formula:
C30H33FN8O2S
Molecular Weight:
588.6988
MDL Number:
MFCD31544330
SMILES:
CCc1nc2n(c1CNc1sc(c(n1)c1ccc(cc1)F)C#N)cc(cc2C)N1CCN(CC1)CC(=O)N1CC(C1)O
Properties
Computed Properties
 
Complexity:
995  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
42  
Hydrogen Bond Acceptor Count:
10  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
7  
XLogP3:
4.8  

Downstream Synthesis Route

[1]CurrentPatentAssignee:GALAPAGOSNV-WO2014/139882,2014,A1

[2]CurrentPatentAssignee:GALAPAGOSNV-WO2014/139882,2014,A1

[3]Desroy,Nicolas;Housseman,Christopher;Bock,Xavier;Joncour,Agnès;Bienvenu,Natacha;Cherel,Laëtitia;Labeguere,Virginie;Rondet,Emilie;Peixoto,Christophe;Grassot,Jean-Marie;Picolet,Olivier;Annoot,Denis;Triballeau,Nicolas;Monjardet,Alain;Wakselman,Emanuelle;Roncoroni,Veronique;LeTallec,Sandrine;Blanque,Roland;Cottereaux,Celine;Vandervoort,Nele;Christophe,Thierry;Mollat,Patrick;Lamers,Marieke;Auberval,Marielle;Hrvacic,Boska;Ralic,Jovica;Oste,Line;VanderAar,Ellen;Brys,Reginald;Heckmann,Bertrand[JournalofMedicinalChemistry,2017,vol.60,#9,p.3580-3590]

[4]Gong,Ping;Jia,Fang;Jiang,Nan;Lei,Hongrui;Li,Changtao;Yang,Yu;Zhai,Xin[Organicprocessresearchanddevelopment,2020,vol.24,#6,p.997-1005]

4640-67-9   
2-2-ethyl-6-4-2-(3-hydroxyazetidin-1-yl)-2-oxoethylpiperazin-1-yl-8-methylimidazo1,2-αpyridin-3-yl-(methyl)amino-4-(4-fluorophenyl)thiazole-5-carbonitrile 

[1]Patent:WO2014/139882,2014,A1

[2]JournalofMedicinalChemistry,2017,vol.60,p.3580-3590

952753-59-2   
2-2-ethyl-6-4-2-(3-hydroxyazetidin-1-yl)-2-oxoethylpiperazin-1-yl-8-methylimidazo1,2-αpyridin-3-yl-(methyl)amino-4-(4-fluorophenyl)thiazole-5-carbonitrile 

[1]CurrentPatentAssignee:GALAPAGOS-WO2014/139882,2014,A1

[2]Desroy,Nicolas;Housseman,Christopher;Bock,Xavier;Joncour,Agnès;Bienvenu,Natacha;Cherel,Laëtitia;Labeguere,Virginie;Rondet,Emilie;Peixoto,Christophe;Grassot,Jean-Marie;Picolet,Olivier;Annoot,Denis;Triballeau,Nicolas;Monjardet,Alain;Wakselman,Emanuelle;Roncoroni,Veronique;LeTallec,Sandrine;Blanque,Roland;Cottereaux,Celine;Vandervoort,Nele;Christophe,Thierry;Mollat,Patrick;Lamers,Marieke;Auberval,Marielle;Hrvacic,Boska;Ralic,Jovica;Oste,Line;VanderAar,Ellen;Brys,Reginald;Heckmann,Bertrand[JournalofMedicinalChemistry,2017,vol.60,#9,p.3580-3590]

[1]CurrentPatentAssignee:GALAPAGOSNV-WO2014/139882,2014,A1

[2]Desroy,Nicolas;Housseman,Christopher;Bock,Xavier;Joncour,Agnès;Bienvenu,Natacha;Cherel,Laëtitia;Labeguere,Virginie;Rondet,Emilie;Peixoto,Christophe;Grassot,Jean-Marie;Picolet,Olivier;Annoot,Denis;Triballeau,Nicolas;Monjardet,Alain;Wakselman,Emanuelle;Roncoroni,Veronique;LeTallec,Sandrine;Blanque,Roland;Cottereaux,Celine;Vandervoort,Nele;Christophe,Thierry;Mollat,Patrick;Lamers,Marieke;Auberval,Marielle;Hrvacic,Boska;Ralic,Jovica;Oste,Line;VanderAar,Ellen;Brys,Reginald;Heckmann,Bertrand[JournalofMedicinalChemistry,2017,vol.60,#9,p.3580-3590]

[1]Gong,Ping;Jia,Fang;Jiang,Nan;Lei,Hongrui;Li,Changtao;Yang,Yu;Zhai,Xin[Organicprocessresearchanddevelopment,2020,vol.24,#6,p.997-1005]

[2]Desroy,Nicolas;Housseman,Christopher;Bock,Xavier;Joncour,Agnès;Bienvenu,Natacha;Cherel,Laëtitia;Labeguere,Virginie;Rondet,Emilie;Peixoto,Christophe;Grassot,Jean-Marie;Picolet,Olivier;Annoot,Denis;Triballeau,Nicolas;Monjardet,Alain;Wakselman,Emanuelle;Roncoroni,Veronique;LeTallec,Sandrine;Blanque,Roland;Cottereaux,Celine;Vandervoort,Nele;Christophe,Thierry;Mollat,Patrick;Lamers,Marieke;Auberval,Marielle;Hrvacic,Boska;Ralic,Jovica;Oste,Line;VanderAar,Ellen;Brys,Reginald;Heckmann,Bertrand[JournalofMedicinalChemistry,2017,vol.60,#9,p.3580-3590]

[3]CurrentPatentAssignee:GALAPAGOSNV-WO2014/139882,2014,A1Locationinpatent:Paragraph00362-00364;00469-00471

Literature

Title: Discovery of 2-[[2-Ethyl-6-[4-[2-(3-hydroxyazetidin-1-yl)-2-oxoethyl]piperazin-1-yl]-8-methylimidazo[1,2-a]pyridin-3-yl]methylamino]-4-(4-fluorophenyl)thiazole-5-carbonitrile (GLPG1690), a First-in-Class Autotaxin Inhibitor Undergoing Clinical Evaluation for the Treatment of Idiopathic Pulmonary Fibrosis.

Journal: Journal of medicinal chemistry 20170511

Title: Selective Inhibition of Autotaxin Is Efficacious in Mouse Models of Liver Fibrosis.

Journal: The Journal of pharmacology and experimental therapeutics 20170101

Title: The autotaxin-lysophosphatidic acid pathway in pathogenesis of rheumatoid arthritis.

Journal: European journal of pharmacology 20151015

Title: Autotaxin production of lysophosphatidic acid mediates allergic asthmatic inflammation.

Journal: American journal of respiratory and critical care medicine 20131015

Title: Lysophosphatidic acid (LPA) and its receptors: role in airway inflammation and remodeling.

Journal: Biochimica et biophysica acta 20130101

Title: Problems of the pathogenesis, clinics, and therapy of panarteritis of the aorta and its branches.

Journal: Cor et vasa 19750101

Title: Desroy N, et al. Discovery of 2-[-Ethyl-6---(3-hydroxyazetidin-1-yl)-2-oxoethylpiperazin-1-yl-8-methylimidazo,2-apyridin-3-ylmethylamino-4-(4-fluorophenyl)thiazole-5-carbonitrile (GLPG1690), a First-in-Class Autotaxin Inhibitor Undergoing Clinical Evaluation for the Treatment of Idiopathic Pulmonary Fibrosis. J Med Chem. 2017 May 11;60(9):3580-3590.

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