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Volumn 13, Issue 6, 2005, Pages 1901-1911

Novel acetylcholinesterase inhibitor as increasing agent on rhythmic bladder contractions: SAR of 8-{3-[1-(3-fluorobenzyl)piperidin-4-yl]propanoyl}- 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (TAK-802) and related compounds

Author keywords

Acetylcholinesterase inhibitor; Pyrrolos 3,2,1 ij quinolin 4 one; Rhythmic bladder contraction; TAK 802

Indexed keywords

2 [[4 [3 OXO 3 (4 OXO 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 8 YL)PROPYL]PIPERIDIN 1 YL]METHYL]BENZONITRILE; 3 (1 BENZYLPIPERIDIN 4 YL) 1 (2,3,4,5 TETRAHYDRO 1,4 BENZOXAZEPIN 7 YL)PROPAN 1 ONE; 3 (1 BENZYLPIPERIDIN 4 YL) 1 (2,3,4,5 TETRAHYDRO 1H 2 BENZAZEPIN 8 YL)PROPAN 1 ONE; 3 (1 BENZYLPIPERIDIN 4 YL) 1 (2,3,4,5 TETRAHYDRO 1H 3 BENZAZEPIN 7 YL)PROPAN 1 ONE; 3 [[4 [3 OXO 3 (4 OXO 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 8 YL)PROPYL]PIPERIDIN 1 YL]METHYL]BENZONITRILE; 4 [[4 [3 OXO 3 (4 OXO 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 8 YL)PROPYL]PIPERIDIN 1 YL]METHYL]BENZONITRILE; 8 [3 (1 BENZYLPIPERIDIN 4 YL)PROPANOYL] 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 4 ONE; 8 [3 (1 BENZYLPIPERIDIN 4 YL)PROPANOYL] 5,6 DIHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 2(IH) ONE; 8 [3 [1 (2 CHLOROBENZYL)PIPERIDIN 4 YL]PROPANOYL] 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 4 ONE; 8 [3 [1 (2 HYDROXYBENZYL)PIPERIDIN 4 YL]PROPANOYL] 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 4 ONE; 8 [3 [1 (2 METHOXYBENZYL)PIPERIDIN 4 YL]PROPANOYL] 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 4 ONE; 8 [3 [1 (2 NITROBENZYL)PIPERIDIN 4 YL]PROPANOYL] 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 4 ONE; 8 [3 [1 (3 CHLOROBENZYL)PIPERIDIN 4 YL]PROPANOYL] 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 4 ONE; 8 [3 [1 (3 FLUOROBENZYL)PIPERIDIN 4 YL]PROPANOYL] 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 4 ONE; 8 [3 [1 (3 HYDROXYBENZYL)PIPERIDIN 4 YL]PROPANOYL] 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 4 ONE; 8 [3 [1 (3 METHOXYBENZYL)PIPERIDIN 4 YL]PROPANOYL] 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 4 ONE; 8 [3 [1 (3 NITROBENZYL)PIPERIDIN 4 YL]PROPANOYL] 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 4 ONE; 8 [3 [1 (4 CHLOROBENZYL)PIPERIDIN 4 YL]PROPANOYL] 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 4 ONE; 8 [3 [1 (4 FLUOROBENZYL)PIPERIDIN 4 YL]PROPANOYL] 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 4 ONE; 8 [3 [1 (4 HYDROXYBENZYL)PIPERIDIN 4 YL]PROPANOYL] 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 4 ONE; 8 [3 [1 (4 METHOXYBENZYL)PIPERIDIN 4 YL]PROPANOYL] 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 4 ONE; 8 [3 [1 (4 NITROBENZYL)PIPERIDIN 4 YL]PROPANOYL] 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 4 ONE; 8,3 [1 (2 FLUOROBENZYL)PIPERIDIN 4 YL]PROPANOYL 1,2,5,6 TETRAHYDRO 4H PYRROLO[3,2,1 IJ]QUINOLIN 4 ONE; 9 [3 (1 BENZYLPIPERIDIN 4 YL)PROPANOYL] 1,2,6,7 TETRAHYDROAZEPINO[3,2,1 HI]INDOL 4(5H) ONE; 9 [3 (1 BENZYLPIPERIDIN 4 YL)PROPANOYL] 2,3,6,7 TETRAHYDRO 1H,5H PYRIDO[3,2,1 IJ]QUINOLIN 5 ONE; BETHANECHOL; CARBAMIC ACID; CHOLINESTERASE INHIBITOR; DISTIGMINE BROMIDE; TAK 802; UNCLASSIFIED DRUG; ZANEPEZIL;

EID: 13844308650     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2005.01.022     Document Type: Article
Times cited : (17)

References (37)
  • 5
    • 85030808019 scopus 로고    scopus 로고
    • U.S. Patent 2,789,981
    • Schmid, O. U.S. Patent 2,789,981
    • Schmid, O.1
  • 22
    • 85030813927 scopus 로고    scopus 로고
    • note
    • para-Nitrobenzyloxycarbonyl group is sufficiently stable toward electrophilic species such as acyl cations, owing to the electron-withdrawing nitro group, and is easily removed by catalytic hydrogenation. Thus, the selective deprotection is feasible without effecting the protecting groups of the heterocyclic moieties (i.e., N-acetyl, N-formyl, and N-trifluoroacetyl groups)
  • 34
    • 85030813201 scopus 로고    scopus 로고
    • note
    • Significant difference was shown when the AUC was doubled or more, so the AUC200 value was adopted as an in vivo parameter. Also see Ref. 16
  • 35
    • 85030814119 scopus 로고    scopus 로고
    • note
    • Intraduodenal administration was adopted instead of po administration, since animals required to be anesthetized during the rhythmic bladder contraction study
  • 36
    • 85030815031 scopus 로고    scopus 로고
    • note
    • The reason why distigmine showed better AUC200 value than its AChE inhibition activity is not clear, but the contributions of distribution or metabolic factors are speculated


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.