352553-60-7Relevant academic research and scientific papers
Efficient asymmetric synthesis of N-[(1R)-6-chloro-2,3,4,9-tetrahydro-1H- carbazol-1-yl]-2-pyridinecarboxamide for treatment of human papillomavirus infections
Boggs, Sharon D.,Cobb, Jeremy D.,Gudmundsson, Kristjan S.,Jones, Lynda A.,Matsuoka, Richard T.,Millar, Alan,Patterson, Daniel E.,Samano, Vicente,Trone, Mark D.,Xie, Shiping,Zhou, Xiao-Ming
, p. 539 - 545 (2007)
An efficient asymmetric synthesis of N-(1R)-6-chloro-2,3,4,9-tetrahydro-1H- carbazol-1-yl]-2-pyridinecarboxamide 1, a potential treatment for human papillomavirus infections, is described. The key step in the synthesis of this molecule is an asymmetric reductive animation directed by chiral (phenyl)-ethylamines resulting in up to 96% disastereo facial selectivity. The synthesis is also highlighted by isolation of a unique 2-picolinic acid salt of (1R)-6-chloro-2,3,4,9-tetrahydro-1H-carbazol-1-amine (13). Subsequent application of 1-propylphosphonic acid cyclic anhydride (T3P) for convenient amide formation from the two components of the salt provides the product 1 in high yield. The process research work leading to the final synthesis includes a racemic synthesis followed by resolution with chiral supercritical fluid chromatography, and an enantioselective reductive animation via chiral transfer hydrogenation catalyzed by Ru(II) complexes of N-[(1S,2S)-2-amino-1,2- diphenylethyl]-1-naphthalenesulfonamide or (R)-BI-NAP. Highlighting the practicality of the synthesis, the process has been scaled up in 200-gallon reactors for delivery of multikilograms of the target compound 1 in over 99.5% enantiomeric purity.
THERAPEUTIC COMPOUNDS AND METHODS TO TREAT INFECTION
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, (2019/01/17)
Disclosed herein are compounds of formula I: or a salt thereof and compositions comprising a compound of formula I or a pharmaceutically acceptable salt thereof. Also disclosed herein are methods for treating or preventing a bacterial infection in an anim
First-generation structure-activity relationship studies of 2,3,4,9-tetrahydro-1H-carbazol-1-amines as CpxA phosphatase inhibitors
Li, Yangxiong,Gardner, Jessi J.,Fortney, Katherine R.,Leus, Inga V.,Bonifay, Vincent,Zgurskaya, Helen I.,Pletnev, Alexandre A.,Zhang, Sheng,Zhang, Zhong-Yin,Gribble, Gordon W.,Spinola, Stanley M.,Duerfeldt, Adam S.
, p. 1836 - 1841 (2019/05/22)
Genetic activation of the bacterial two-component signal transduction system, CpxRA, abolishes the virulence of a number of pathogens in human and murine infection models. Recently, 2,3,4,9-tetrahydro-1H-carbazol-1-amines were shown to activate the CpxRA
HCV INHIBITORS
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, (2009/07/03)
The present invention relates to compounds that are useful in the treatment of viruses belonging to Flaviviridae, including flaviviruses, pestiviruses, and hepaciviruses. The invention includes compounds useful for the treatment or prophylaxis of dengue fever, yellow fever, West Nile virus, and HCV.
HCV INHIBITORS
-
, (2009/07/17)
The present invention relates to compounds that are useful in the treatment of viruses belonging to Flaviviridae, including flaviviruses, pestiviruses, and hepaciviruses. The invention includes compounds useful for the treatment or prophylaxis of dengue fever, yellow fever, West Nile virus, and HCV.
HCV INHIBITORS
-
, (2009/07/17)
The present invention relates to compounds that are useful in the treatment of viruses belonging to Flaviviridae, including flaviviruses, pestiviruses, and hepaciviruses. The invention includes compounds useful for the treatment or prophylaxis of dengue fever, yellow fever, West Nile virus, and HCV.
TETRAHYDROCARBAZOLE DERIVATIVES AND THEIR PHARMACEUTICAL USE
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Page 28-29, (2008/06/13)
The present invention relates to novel compounds of formula (I), that are useful in the treatment of human papillomaviruses, and also to the methods for the making and use of such compounds.
TETRAHYDROCARBAZOLE DERIVATIVES AND THEIR PHARMACEUTICAL USE
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, (2010/02/09)
The present invention relates to novel compounds of formula (I) that are useful in the treatment of human papillomaviruses, and also to the methods for the making and use of such compounds.
