163
Views
31
CrossRef citations to date
0
Altmetric
Review

Inhibitors of PDE4: a review of recent patent literature

Pages 773-787 | Published online: 13 Jul 2005

Bibliography

  • NICHOLSON CD, CHALLISS RAJ, SHAHID M: Differential modulation of tissue function and therapeutic potential of selective inhibitors of cyclic nucleotide phosphodiesterase isoenzymes. Trends PharmacoL (1991) 12:19–27.
  • NICHOLSON CD, SHAHID M: Inhibitors of cyclic nucleotide phosphodiesterase isoenzymes - their potential utility in the therapy of asthma. Pulm. PharmacoL (1994) 7:1–17.
  • CONTI M, JIN LS: The molecular biology of cyclic nucleotide phosphodiesterases. Frog. Nucleic Acid Res. MoL Biol. (1999) 63:1–38.
  • •A comprehensive review of PDE4 biology.
  • TORPHY TJ: Phosphodiesterase isozymes: molecular targets for novel anti-asthma agents. Am. J. Respir. Crit. Care Med. (1998) 157:351–370.
  • •Comprehensive review on PDE4 inhibition.
  • HOROWSKI R, SASTRE-Y- HERNANDEZ M. Curr. Ther. Res. (1998) 38:23–29.
  • SOUNESS JE, RAO S: A proposal for pharmacologically distinct conformers of PDE4. Cell. signal. (1997) 9:227–236.
  • LALIBERTE F, HAN Y, GOVINDARAJAN A et al.: Conformational difference between PDE4 apoenzyme and holoenzyme. Biochemistry (2000) 39(21):6449–6458.
  • LIU S, LALIBERTE F, BOBECHKO B et al.: Dissecting the cofactor-dependent and independent bindings of PDE4 inhibitors. Biochemistry (2001) 40(34) :10179–10186.
  • GLAXOSMITHKLINE, INC.: GlaxoSmithKline receives FDA approvable letter for Ariflo (cilomilast) tablets 15 mg. Press release (27 October 2003).
  • •This information is not peer-reviewed.
  • CHRISTENSEN SB, GUIDER A, FORSTER CJ et al.: 1,4-Cyclohexanecarboxylates: potent and selective inhibitors of phosphodiesterase 4 for the treatment of asthma. J. Med. Chem. (1998) 41:821–835.
  • REISNER T et al.: Cilomilast is efficacious in chronic obstructive pulmonary disease (COPD). Eur. Respir. J. (2003) 22\(Supp1.5): Abst. P530.
  • FERGUSON G, FISCHER TL, MORIS A et al.: Cardiovascular safety of cilomilast in patients with chronic obstructive pulmonary disease. Chest (2003) 124\(Supp1.4):171S.
  • RABE F, O'DONNELL D, MUIR F et aL: Roflumilast, an oral, once-daily PDE4 inhibitor, improves lung function and reduces exacerbation rates in patients with COPD. Eur. Respir. J. (2004) 24\(Supp1.48): Abst. 267.
  • BETHKE TD, BATEMAN ED, VAN NOORD JA et aL: Long-term safety of roflumilast in the treatment of chronic obstructive pulmonary disease. Chest (2004) 126\(Supp1.4):8055.
  • HUENNEMEYER A, ZECK K, BETHKE TD et al.: Oral, once-daily roflumilast and its active N-oxide metabolite exhibit dose proportional pharmacokinetics between 250 ug and 500 ug. Chest (2004) 126\(Supp1.4):8045.
  • MANEGOLD A, HAUNS B, HUENNEMEYER A et aL: Pharmacokinetics of roflumilast and its active metabolite roflumilast N-oxide is not influenced by erythromycin. Eur. Respir. J. (2004) 24\(Supp1.48): Abst. P867
  • HAUNS B, HUENNEMEYER A, KILIAN U et al.: Lack of pharmacokinetic interaction of roflumilast and its oxide metabolite, roflumilast N-oxide, with budesonide or salbutamol. 4th World Asthma Meet (16 Feb - 19 Feb 2004) Bangkok: Abst. P229–P230.
  • BARDIN PG, VAN SCHALKWYK EM, VAN HEERDEN K et aL: Inhibition of late asthmatic reaction in allergic asthma by roflumilast, a selective phosphodiesterase 4 inhibitor. 4th World Asthma Meet (16–19 Feb 2004) Bangkok: Abst. 0–228.
  • BATEMAN D, IZQUIERDO L, VETTER N et al.: Roflumilast, a selective phosphodiesterase 4 inhibitor, shows efficacy and safety in the long-term treatment of asthma. Eur. Respir. J. (2003) 22\(Supp1.45): Abst. 1393
  • WOLLIN L, BARSIG J, MARX D et al.: Eur. Respir. J. (2003) 22\(Supp1.45): Abst. P739.
  • TIMMER W, LECLERC V, BIRRAUX G et al.: The new phosphodiesterase 4 inhibitor roflumilast is efficacious in exercise-induced asthma and leads to suppression of LPS-stimulated TNF-a ex vivo. J. Clin. Pharmacol (2002) 42(3):297.
  • CHIHIRO M, NAGAMOTO H, TAKEMURA I et al.: Novel thiazole derivatives as inhibitors of superoxide production by human neutrophils: synthesis and structure-activity relationships. J. Med. Chem. (1995) 38:353–358.
  • ONAGAWA T, NAGAMOTO H, MAEDA T et al.: j MoL Cell Cardio. (1998) 30: Abst. 37.
  • NAGAMOTO H, MAEDA T, SUEYOSHI H et al.: OPC-6535 inhibits human and porcine monocyte tumor necrosis factor-a production in vitro and in vivo. Gastroenterology (2004) 126(4, Supp1.2): Abst. W1090.
  • HANAUER SB, MINER PB, KESHAVARZIAN A et al.: Randomized, double-blind, placebo-controlled, parallel arm, safety and efficacy trial of once-daily, oral OPC-6535 in the treatment of active ulcerative colitis (UC). Gastroenterology (2004) 126(4, Supp1.2): Abst. 814.
  • KALGUTKAR AS, CHOO E, TAYLOR TJ, MARFAT A: Disposition of CP-671,305, a selective phosphodiesterase 4 inhibitor in preclinical species. Xenobiotica (2004) 34(8):755–770.
  • LOHER F, SCHMALL K, FREYTAG P et al.: The specific type-4 phosphodiesterase inhibitor mesopram alleviates experimental colitis in mice. J. Pharmacol. Exp. Thor. (2003) 305(2):549–556.
  • MARX D, POPPE H, KUESTERS S, HEER S, SZELENYI I: The pharmacological activity ofAWD 12-281, a potent phosphodiesterase 4 (PDE4) inhibitor for the treatment of allergic rhinitis and asthma. Pneumologie (1999) 53(9):443.
  • KUSS H, HOEFGEN N, JOHANSSEN S et al.: In vivo efficacy in airway disease models of N-(3,5-dichloropyridin-4-y1)-11-(4-fluorobenzy1-5-hydroxy-indole-3-y11-glyoxidic acid amide (AWD 12-281), a selective phosphodiesterase 4 inhibitor for inhaled administration. J. Pharmacol Exp. Thor. (2003) 307(1):373.
  • KUSS H, HOEFGEN N, RUNDFELDT C et al.: AWD 12–281, a new PDE4-inhibitor, suppresses allergen-induced 'early phase' bronchoconstriction in sensitized guinea pigs. Eur. Respir. J. (2003) 22\(Supp1.45): Abst. 107S.
  • ICOS CORP.: Phase II study of IC485 inCOPD does not meet primary efficacy endpoint; ongoing PDE4 program to focus on preclinical candidates. Press release (23 March 2005).
  • FURUIE H, NAKAGAWA S, KAWASHIMA M et al.: Suppressive effect of novel phosphodiesterase 4 (PDE4) inhibitor ONO-6126 on TNF-a release was increased after repeated oral administration in healthy Japanese subjects. Eur. Respir. J. (2003) 22\(Supp1.45): Abst. 2557.
  • TAKEDA H et al.: Pharmacological profileof Ono-6126, a novel phosphodiesterase 4 (PDE4) inhibitor. 98th Int.Conf Am. Thorac. Soc. Atlanta, USA (17 May - 22 May 2002): Abst. H41.
  • MEMORY PHARM.: Memory Pharmaceuticals provides update on PDE4 collaboration with Roche. Press release (15 April 2005).
  • HELICON THERAPEUTICS, INC.: Helicon Therapeutic, Inc. commences Phase I human testing of the company's lead drug candidate. News Release (10 December 2004).
  • BOURTCHOULADZE R, LIDGE R, CATAPANO R et al.: A mouse model of Rubinstein-Taybi syndrome: defective long-term memory is ameliorated by inhibitors of phosphodiesterase 4. Proc. Natl. Acad. Sci. USA (2003) 100(18):10518.
  • VAKKALANKA SK, BALASUBRAIVIANIAM G, GHARAT LA et al.: The pharmacological and safety profile of a novel selective phosphodiesterase-4 (PDE4) inhibitor: GRC-3886. Eur. Respir. J. (2004) 24\(Supp1.48): Abst. P1391
  • UNDERWOOD DC, KOTZER CJ, BOCHNOWICZ S et al.: Comparison of phosphodiesterase III, IV and dual III/IV inhibitors on bronchospasm and pulmonary eosinophilia influx in guinea pigs. J. Pharmacol Exp. Thor. (1994) 270(1):250–259.
  • COLUCCI WS, WRIGHT RF, BRAUNWALD E: New positive inotropic agents in the treatment of congestive heart failure. Mechanism of action and recent clinical developments. N Engl. J. Med. (1986) 314(6):349–358.
  • TRIFILIEFF A, WYSS D, WALKER C et al.: Pharmacological profile of a novel phosphodiesterase 4 inhibitor, 4-(8-benzo11,2,51-oxadiazol-5-y1-11,71-naphthyridin-6-y1)-benzoic acid (NVP-ABE171), a 1,7-naphthyridine derivative with anti-inflammatory activities. Pharmacol Exp. Ther. (2002) 301(1):241–248.
  • OCHIAI H, OHTAMI T, ISHIDA A et ell.: Highly potent PDE4 inhibitors with therapeutic potential. Bioorg. Med. Chem. (2004) 12(17):4645–4665.
  • ZHANG HT, CRISSMAN AM, DORAIRAJ NR et al.: Inhibition of cyclic phosphodiesterase (PDE4) reverses memory deficits associated with NMDA receptor antagonism. Neuropsychopharmacology (2000) 23:198–204.
  • JIN SL, CONTI M: Induction of cyclic nucleotide phosphodiesterase PDE4B is essential for LPS-activated TNF-a responses. Proc. Nail. Acad. Sci. USA (2002) 99(11):7628–7633.
  • MEHATS C, JIN SL, WAHLSTROM J et al.: PDE4D plays a critical role in the control of airway smooth muscle contraction. FASEB (2003) 17(13):1831–1841.
  • ROBICHAUD A, STAMATIOU A, JIN SL: Deletion of phosphodiesterase 4D in mice shortens a2-adrenoceptor-mediated anesthesia, a behavioral correlate of emesis. Clin. Invest. (2002) 110(7):1045–1052.
  • XU RX, HASSELL AM, VANDERWALL D et al.: Atomic structure of PDE4: insights into phosphodiesterase mechanism and specificity. Science (2000) 288: 1822-1825.
  • •This is the first report of a catalytic domain of a phosphodiesterase. The structure is that of PDE4B2 and the resolution is 1.77 A.
  • HUM Q, COLICELLI J, KE H: The crystal structure of AMP-bound PDE4D suggests a mechanism for phosphodiesterase catalysis. Biochemistry (2003) 42(45):13220–13226.
  • LEE ME, MARKOWITZ J, LEE JO et al.: Crystal structure of phosphodiesterase 4D and inhibitor complex. FEBS Lett. (2002) 530:53–58.
  • HUM Q, WANG H, KIM H-Y et al.: Three-dimensional structures of PDE4D in complex with rolipram and implications on inhibitor selectivity. Structure (2003) 11(7):865–873. 785
  • XU RX, ROCQUE WJ, LAMBERT MH et al.: Crystal structures of the catalytic domain of phosphodiesterase 4B complexed with AMP, 8-Br-AMP, and rolipram. J. Mol. Biol. (2004) 337(2):355–365
  • CARD GL, ENGLAND BP, SUZUKI Y et al.: Structural basis for the activity of drugs that inhibit phosphodiesterases. Structure (2004) 12(12):2233–2247
  • CARD G, BLASDEL L, ENGLAND BP et al.: A family of phosphodiesterase inhibitors discovered by cocrystallography and scaffold-based drug design. Nat. Biotechnol. (2005) 23(2):201–207.
  • PLEXXIKON, INC.: Robust discovery platform accelerates developments of selective inhibitors for respiratory disease. Press release (13 November 2003).
  • •This information is not peer-reviewed.
  • ZHANG KY, CARD GL, SUZUKI Yet al.:A glutamine switch mechanism for nucleotide selectivity by phosphodiesterases. Mol. Cell (2004) 15:279–286.
  • MANALLACK DT, HUGHES RA, THOMPSON PE: The next generation of phosphodiesterase inhibitors: structural clues to ligand and substrate selectivity of phosphodiesterases. J. Med. Chem. (2005) 48(10):3449–3462.
  • •A good structural overview of phosphodiesterase isoenzymes and a molecular basis for selective ligand/inhibitor recognition.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.