78543-07-4Relevant academic research and scientific papers
Discovery of 2-(3,5-difluoro-4-methylsulfonaminophenyl)propanamides as potent TRPV1 antagonists
Kim, Changhoon,Ann, Jihyae,Lee, Sunho,Sun, Wei,Blumberg, Peter M.,Frank-Foltyn, Robert,Bahrenberg, Gregor,Stockhausen, Hannelore,Christoph, Thomas,Lee, Jeewoo
, p. 2539 - 2542 (2018/06/07)
A series of A-region analogues of 2-(3-fluoro-4-methylsufonamidophenyl) propanamide 1 were investigated as TRPV1 antagonists. The analysis of structure-activity relationship indicated that a fluoro group at the 3- (or/and) 5-position and a methylsulfonamido group at the 4-position were optimal for antagonism of TRPV1 activation by capsaicin. The most potent antagonist 6 not only exhibited potent antagonism of activation of hTRPV1 by capsaicin, low pH and elevated temperature but also displayed highly potent antagonism of activation of rTRPV1 by capsaicin. Further studies demonstrated that antagonist 6 blocked the hypothermic effect of capsaicin in vivo, consistent with its in vitro mechanism, and it showed promising analgesic activity in the formalin animal model.
SUBSTITUTED OXAZOLE- AND THIAZOLE-BASED CARBOXAMIDE AND UREA DERIVATIVES AS VANILLOID RECEPTOR LIGANDS II
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Page/Page column 25; 32, (2016/06/14)
The invention relates to oxazole and thiazole-based carboxamide and urea derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
SUBSTITUTED PYRAZOLYL-BASED CARBOXAMIDE AND UREA DERIVATIVES BEARING A PHENYL MOIETY SUBSTITUTED WITH AN N-CYCLIC GROUP AS VANILLOID RECEPTOR LIGANDS
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Page/Page column 56, (2013/05/23)
The invention relates to substituted pyrazolyl-based carboxamide and urea derivatives bearing a phenyl moiety substituted with an N-cyclic group as vanilloid receptor ligands formula (S) to pharmaceutical compositions containing these compounds of the general formula (S) and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
SUBSTITUTED PYRAZOLYL-BASED CARBOXAMIDE AND UREA DERIVATIVES BEARING A PHENYL MOIETY SUBSTITUTED WITH AN O-CONTAINING GROUP AS VANILLOID RECEPTOR LIGANDS
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Page/Page column 84, (2013/05/23)
The invention relates to substituted pyrazolyl-based carboxamide and urea derivatives of formula (Q) as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
Amine Substituted Methanesulfonamide Derivatives as Vanilloid Receptor Ligands
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Paragraph 0649; 0651, (2013/04/10)
The invention relates to amine substituted methanesulfonamide derivatives as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
SUBSTITUTED PYRAZOLYL-BASED CARBOXAMIDE AND UREA DERIVATIVES BEARING A PHENYL MOIETY SUBSTITUTED WITH AN N-CONTAINING GROUP AS VANILLOID RECEPTOR LIGANDS
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Page/Page column 84; 86; 87;89; 91, (2013/05/23)
The invention relates to substituted pyrazolyl-based carboxamide and urea derivatives of formula (R) bearing a phenyl moiety substituted with an N-containing group as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
AMINE SUBSTITUTED METHANESULFONAMIDE DERIVATIVES AS VANILLOID RECEPTOR LIGANDS
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Page/Page column 97; 98, (2013/04/13)
The invention relates to amine substituted methanesulfonamide derivatives of formula (I) as vanilloid receptor ligands, to pharmaceutical compositions containing these compounds and also to these compounds for use in the treatment and/or prophylaxis of pain and further diseases and/or disorders.
N-4-t-Butylbenzyl 2-(4-methylsulfonylaminophenyl) propanamide TRPV1 antagonists: Structure-activity relationships in the A-region
Kim, Yong Soo,Kil, Min-Jung,Kang, Sang-Uk,Ryu, Hyungchul,Kim, Myeong Seop,Cho, Yongsung,Bhondwe, Rahul S.,Thorat, Shivaji A.,Sun, Wei,Liu, Keliang,Lee, Jin Hee,Choi, Sun,Pearce, Larry V.,Pavlyukovets, Vladimir A.,Morgan, Matthew A.,Tran, Richard,Lazar, Jozsef,Blumberg, Peter M.,Lee, Jeewoo
experimental part, p. 215 - 224 (2012/02/16)
Structure-activity relationships for the A-region in a series of N-4-t-butylbenzyl 2-(4-methylsulfonylaminophenyl) propanamides as TRPV1 antagonists have been investigated. Among them, the 3-fluoro analogue 54 showed high binding affinity and potent antagonism for both rTRPV1 and hTRPV1 in CHO cells. Its stereospecific activity was demonstrated with marked selectivity for the (S)-configuration (54S versus 54R). A docking study of 54S with our hTRPV1 homology model highlighted crucial hydrogen bonds between the ligand and the receptor contributing to its potency.
SUBSTITUTED PHENYLLUREAS AND PHENYLAMIDES AS VANILLOID RECEPTOR LIGANDS
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Page/Page column 100; 103, (2010/11/18)
The invention relates to substituted phenylureas and phenylamides of formula (I), to processes for the preparation thereof, to pharmaceutical compositions containing these compounds and also to the use of these compounds for preparing pharmaceutical compositions.
Stereospecific high-affinity TRPV1 antagonists: Chiral N-(2-benzyl-3- pivaloyloxypropyl) 2-[4-(methylsulfonylamino)phenyl]propionamide analogues
Ryu, Hyungchul,Jin, Mi-Kyoung,Su, Yeon Kim,Choi, Hyun-Kyung,Kang, Sang-Uk,Dong, Wook Kang,Lee, Jeewoo,Pearce, Larry V.,Pavlyukovets, Vladimir A.,Morgan, Matthew A.,Tran, Richard,Toth, Attila,Lundberg, Daniel J.,Blumberg, Peter M.
, p. 57 - 67 (2008/09/18)
Previously, we reported the thiourea antagonists 2a and 2b as potent and high affinity TRPV1 antagonists. For further optimization of the lead compounds, a series of their amide and α-substituted amide surrogates were investigated and novel chiral N-(2-be
