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Volumn 47, Issue 12, 2004, Pages 3163-3179

Synthesis and structure-activity relationships of a novel series of 2,3,5,6,7,9-hexahydrothieno[3,2-b]quinoline-8(4H)-one 1,1-dioxide K ATP channel openers: Discovery of (-)-(9S)-9-(3-bromo-4-fluorophenyl)-2,3,5,6,7,9-hexahydrothieno[3,2-b] quinolin-8(4H)-one 1,1-dioxide (A-278637), a potent KATP opener that selectively inhibits spontaneous bladder contractions

Author keywords

[No Author keywords available]

Indexed keywords

2 CYANO 1 (1,1 DIMETHYLPROPYL) 3 (3 PYRIDYL)GUANIDINE; 2,3,5,6,7,9 HEXAHYDROTHIENO[3,2 B]QUINOLINE 8(4H) ONE 1,1 DIOXIDE DERIVATIVE; 4 [3,4 DIOXO 2 (1,2,2 TRIMETHYLPROPYLAMINO) 1 CYCLOBUTENYLAMINO] 3 ETHYLBENZONITRILE; 9 (3 BROMO 4 FLUOROPHENYL) 2,3,5,6,7,9 HEXAHYDROTHIENO[3,2 B]QUINOLIN 8(4H) ONE 1,1 DIOXIDE; 9 (3 CYANOPHENYL) 3,4,6,7,9,10 HEXAHYDRO 1,8(2H,5H) ACRIDINEDIONE; A 278637; CROMAKALIM; N (4 BENZOYLPHENYL) 3,3,3 TRIFLUORO 2 HYDROXY 2 METHYLPROPIONAMIDE; POTASSIUM CHANNEL; POTASSIUM CHANNEL STIMULATING AGENT; UNCLASSIFIED DRUG; WAY 133637;

EID: 2542623187     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm030356w     Document Type: Article
Times cited : (54)

References (38)
  • 1
    • 0033027682 scopus 로고    scopus 로고
    • The overactive bladder: Current aetiological concepts
    • Bosch, J. L. H. R. The overactive bladder: Current aetiological concepts. BJU Int. 1999, 83, 7-9.
    • (1999) BJU Int. , vol.83 , pp. 7-9
    • Bosch, J.L.H.R.1
  • 2
    • 0031466747 scopus 로고    scopus 로고
    • A myogenic basis for the overactive bladder
    • Brading, A. F. A Myogenic Basis for the Overactive Bladder. Urology 1997, 50, 57-67.
    • (1997) Urology , vol.50 , pp. 57-67
    • Brading, A.F.1
  • 3
    • 0030667591 scopus 로고    scopus 로고
    • Smooth muscle of the bladder in the normal and the diseased state: Pathophysiology, diagnosis and treatment
    • Turner, W. H.; Brading, A. F. Smooth Muscle of the Bladder in the Normal and the Diseased State: Pathophysiology, Diagnosis and Treatment. Pharmacol. Ther. 1997, 75, 77-110.
    • (1997) Pharmacol. Ther. , vol.75 , pp. 77-110
    • Turner, W.H.1    Brading, A.F.2
  • 4
    • 0344544985 scopus 로고    scopus 로고
    • Discussion: Cellular physiology of detrusor smooth muscle and the development of bladder instability: Possible mechanisms
    • Fry, C. H. Discussion: Cellular Physiology of Detrusor Smooth Muscle and the Development of Bladder Instability: Possible Mechanisms. Urology 1997, 50, 70-71.
    • (1997) Urology , vol.50 , pp. 70-71
    • Fry, C.H.1
  • 5
    • 0029113229 scopus 로고
    • Pharmacology of incontinence
    • Wein, A. J. Pharmacology of Incontinence. Urol. Clin. N. Am. 1995, 22, 557-577.
    • (1995) Urol. Clin. N. Am. , vol.22 , pp. 557-577
    • Wein, A.J.1
  • 6
    • 0035184357 scopus 로고    scopus 로고
    • Pharmacological agents for the treatment of urinary incontinence due to overactive bladder
    • Wein, A. J. Pharmacological agents for the treatment of urinary incontinence due to overactive bladder. Exp. Opin. Invest. Drugs 2001, 10, 65-83.
    • (2001) Exp. Opin. Invest. Drugs , vol.10 , pp. 65-83
    • Wein, A.J.1
  • 9
    • 0035942510 scopus 로고    scopus 로고
    • Recent developments in the biology and medicinal chemistry of potassium channel modulators: Update from a decade of progress
    • Coghlan, M. J.; Carroll, W. A.; Gopalakrishnan, M. Recent Developments in the Biology and Medicinal Chemistry of Potassium Channel Modulators: Update from a Decade of Progress. J. Med. Chem. 2001, 44, 1627-1653.
    • (2001) J. Med. Chem. , vol.44 , pp. 1627-1653
    • Coghlan, M.J.1    Carroll, W.A.2    Gopalakrishnan, M.3
  • 10
    • 0031309603 scopus 로고    scopus 로고
    • The overactive bladder: Pharmacologic basis of drug treatment
    • Andersson, K.-E. The Overactive Bladder: Pharmacologic Basis of Drug Treatment. Urology 1997, 50, 74-84.
    • (1997) Urology , vol.50 , pp. 74-84
    • Andersson, K.-E.1
  • 11
    • 0025871034 scopus 로고
    • The effect of cromakalim on the normal and hyperreflexic human detrusor muscle
    • Nurse, D. E.; Restorick, J. M.; Mundy, A. R. The Effect of Cromakalim on the Normal and Hyperreflexic Human Detrusor Muscle. Brit. J. Urol. 1991, 68, 27-31.
    • (1991) Brit. J. Urol. , vol.68 , pp. 27-31
    • Nurse, D.E.1    Restorick, J.M.2    Mundy, A.R.3
  • 16
    • 0031467256 scopus 로고    scopus 로고
    • ATP channel activator
    • ATP Channel Activator. Cardiovasc. Drug Rev. 1997, 15, 220-231.
    • (1997) Cardiovasc. Drug Rev. , vol.15 , pp. 220-231
    • Li, J.H.1
  • 17
    • 0030985631 scopus 로고    scopus 로고
    • + channels by Zeneca ZD6169 in guinea pig bladder smooth muscle cells
    • + Channels by Zeneca ZD6169 in Guinea Pig Bladder Smooth Muscle Cells. J. Pharmacol. Exp. Ther. 1997, 280, 38-45.
    • (1997) J. Pharmacol. Exp. Ther. , vol.280 , pp. 38-45
    • Hu, S.1    Kim, H.S.2
  • 18
    • 0000395990 scopus 로고
    • Potassium channel activating agents; emerging trends
    • Primeau, J.; Butera, J. A. Potassium Channel Activating Agents; Emerging Trends. Curr. Pharm. Des. 1995, 1, 391-406.
    • (1995) Curr. Pharm. Des. , vol.1 , pp. 391-406
    • Primeau, J.1    Butera, J.A.2
  • 19
    • 0029006222 scopus 로고
    • Recent advances in the chemistry of potassium channel openers
    • Pirotte, B.; Fontaine, J.; Lebrun, P. Recent Advances in the Chemistry of Potassium Channel Openers. Curr. Med. Chem. 1995, 2, 573-582.
    • (1995) Curr. Med. Chem. , vol.2 , pp. 573-582
    • Pirotte, B.1    Fontaine, J.2    Lebrun, P.3
  • 21
    • 1542457191 scopus 로고
    • Synthesis of novel cyclic sulfone dihydropyridines facilitated by a selective ethyl diazoacetate ring expansion
    • Dodd, J. H.; Schwender, C. F.; Gray-Nunez, Y. Synthesis of Novel Cyclic Sulfone Dihydropyridines Facilitated by a Selective Ethyl Diazoacetate Ring Expansion. J. Heterocycl. Chem. 1990, 27, 1453-1456.
    • (1990) J. Heterocycl. Chem. , vol.27 , pp. 1453-1456
    • Dodd, J.H.1    Schwender, C.F.2    Gray-Nunez, Y.3
  • 24
    • 0036176599 scopus 로고    scopus 로고
    • Spontaneous phasic activity of the pig urinary bladder smooth muscle: Characteristics and sensitivity to potassium channel modulators
    • Buckner, S. A.; Milicic, I.; Daza, A. V.; Coghlan, M. J.; Gopalakrishnan, M. Spontaneous phasic activity of the pig urinary bladder smooth muscle: Characteristics and sensitivity to potassium channel modulators, Br. J. Pharmacol, 2002, 135, 639-648.
    • (2002) Br. J. Pharmacol. , vol.135 , pp. 639-648
    • Buckner, S.A.1    Milicic, I.2    Daza, A.V.3    Coghlan, M.J.4    Gopalakrishnan, M.5
  • 25
    • 0037274940 scopus 로고    scopus 로고
    • Effects of ATP-sensitive potassium channel openers and tolterodine on unstable bladder contractions in a pig model of partial bladder outlet obstruction
    • Fey, T. A.; Gopalakrishnan, M.; Strake, J. G.; King, L. L.; Brioni, J. D.; Sullivan, J. P.; Coghlan, M. J.; Brune, M. E. Effects of ATP-Sensitive Potassium Channel Openers and Tolterodine on Unstable Bladder Contractions in a Pig Model of Partial Bladder Outlet Obstruction. Neurol. Urodynamics 2003, 22, 147-155.
    • (2003) Neurol. Urodynamics , vol.22 , pp. 147-155
    • Fey, T.A.1    Gopalakrishnan, M.2    Strake, J.G.3    King, L.L.4    Brioni, J.D.5    Sullivan, J.P.6    Coghlan, M.J.7    Brune, M.E.8
  • 26
    • 2642515981 scopus 로고    scopus 로고
    • note
    • Vehicle studies demonstrated that the anesthetized pigs maintained a stable baseline cystometrogram for the 90 min study period. For further details of these studies please see ref 25.
  • 27
    • 0028306293 scopus 로고
    • Medicinal chemistry of DHP-like calcium antagonists
    • Mannhold, R. Medicinal Chemistry of DHP-Like Calcium Antagonists. Drugs Today 1994, 30, 103-122.
    • (1994) Drugs Today , vol.30 , pp. 103-122
    • Mannhold, R.1
  • 28
    • 0033786692 scopus 로고    scopus 로고
    • Radiotelemetered cystometry in pigs: Validation and comparison of natural filling versus diuresis cystometry
    • Mills, I. W.; Noble, J. G.; Brading, A. F. Radiotelemetered Cystometry in Pigs: Validation and Comparison of Natural Filling Versus Diuresis Cystometry. J. Urol. 2000, 164, 1745-1750.
    • (2000) J. Urol. , vol.164 , pp. 1745-1750
    • Mills, I.W.1    Noble, J.G.2    Brading, A.F.3
  • 30
    • 2642513582 scopus 로고    scopus 로고
    • note
    • The predictive value of the conscious pig CV studies can be appreciated by considering them in the context of data for (-)-cromakalim from a human clinical trial,32 where an average HR increase of 24 ± 7% was recorded 15 min after a maximum plasma concentration of 51 nM was achieved. In these pig studies, an average HR increase for (-)-cromakalim of 38 ± 10% over a 30 min period correlated with a plasma level of 44 nM. Taking into account the variability in the HR and the different sampling times relative to measurement of the physiological effect, this comparison supports these PK/PD relationships for CV effects as predictive for humans.
  • 31
    • 2642570562 scopus 로고    scopus 로고
    • note
    • ATP openers showed a weak correlation: slope = 0.47, r = 0.39.
  • 33
    • 84979320880 scopus 로고
    • On the identification of 1,4-disubstituted hydrocarbons
    • Rinkes, I. J. On the Identification of 1,4-Disubstituted Hydrocarbons. Recl.-Trav. Chim. Pays-Bas 1945, 64, 205-213.
    • (1945) Recl.-Trav. Chim. Pays-Bas , vol.64 , pp. 205-213
    • Rinkes, I.J.1
  • 35
    • 0030030361 scopus 로고    scopus 로고
    • Benzofurazanyl- and benzofuroxanyl-1,4-dihydropyridines: Synthesis, structure and calcium entry blocker activity
    • Gasco, A. M.; Ermondi, G.; Fruttero, R.; Gasco, A. Benzofurazanyl- and benzofuroxanyl-1,4-dihydropyridines: Synthesis, structure and calcium entry blocker activity. Eur. J. Med. Chem. Chim. Ther. 1996, 31, 3-10.
    • (1996) Eur. J. Med. Chem. Chim. Ther. , vol.31 , pp. 3-10
    • Gasco, A.M.1    Ermondi, G.2    Fruttero, R.3    Gasco, A.4
  • 36
    • 37049082930 scopus 로고
    • Magnesium-mediated ortho-specific formylation and formaldoximation of phenols
    • Aldred, R.; Johnston, R.; Levin, D.; Neilan, J. Magnesium-mediated ortho-Specific Formylation and Formaldoximation of Phenols. J. Chem. Soc. Perkin Trans. 1 1994, 13, 1823-1832.
    • (1994) J. Chem. Soc. Perkin Trans. 1 , vol.13 , pp. 1823-1832
    • Aldred, R.1    Johnston, R.2    Levin, D.3    Neilan, J.4
  • 37
    • 84970577951 scopus 로고
    • B receptor antagonists. III folded baclofen analogues based on phthalide
    • B Receptor Antagonists. III Folded Baclofen Analogues Based on Phthalide. Aust. J. Chem. 1989, 42, 787-795.
    • (1989) Aust. J. Chem. , vol.42 , pp. 787-795
    • Donati, C.1    Prager, R.H.2    Weber, B.3
  • 38
    • 0025037110 scopus 로고
    • Novel 1,4-dihydropyridine calcium antagonists. I. Synthesis and hypotensive activity of 4-(substituted pyridyl)-1,4-dihydropyridine derivatives
    • Ashimori, A.; Ono, T.; Uchida, T.; Ohtaki, Y.; Fukaya, C.; Watanabe, M.; Yokoyama, K. Novel 1,4-Dihydropyridine Calcium Antagonists. I. Synthesis and Hypotensive Activity of 4-(Substituted Pyridyl)-1,4-dihydropyridine Derivatives. Chem. Pharm. Bull. 1990, 38, 2446-2458.
    • (1990) Chem. Pharm. Bull. , vol.38 , pp. 2446-2458
    • Ashimori, A.1    Ono, T.2    Uchida, T.3    Ohtaki, Y.4    Fukaya, C.5    Watanabe, M.6    Yokoyama, K.7


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