Selective phosphodiesterase 4 inhibitors - Emerging trends in asthma therapy (Antiasthmatics-3)

Journal of Scientific and Industrial Research

Volumn 62, Issue 6, 2003, Pages 537-553

  Gupta, Ranju ^a   Gandhi, Deepika ^a   Jindal, Dharam Paul ^a  

^a PANJAB UNIVERSITY   (India)

Author keywords

Antiasthmatics; Asthma therapy; Isozyme; Nitraquazone; Phosphodiesterase 4 inhibitors; Rolipram; Xanthines

Indexed keywords

ASTHMA; HEALTH CARE;

BRONCHUS;

EID: 0037631471     PISSN: 00224456     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (76)

1. Torphy T J, Pospodiesterase isozymes : molecular targets for novel antiasthma agents, Am J Respir Crit Care Med, 157 (1998) 351.
2. Barnette M S, Phosphodiesterase 4 (PDE4) inhibitors in asthma and chronic obstructive pulmonary disease (COPD), Prog Drug Res, 53 (1999) 193.
3. Crocker C I & Townely R G, Therapeutic potential of Phosphodiesterase 4 inhibitors in allergic diseases, Drugs Today, 35 (1999) 519.
4. Juilfs D M, Soderling S, Burns F & Beavo J A, Cyclic GMP as substrate and regulator of cyclic nucleotide phosphodiesterases (PDEs), Rev Physiol Biochem Pharmacol, 135 (1999) 67.
5. Connor D T & Unangst P C, In Burger's Medicinal chemistry and drug discovery, antiallergic agents, edited by Wolff M E (John Wiley and Sons Inc, New York) 1996, 511.
6. Burnouf C, Auclair E, Avenel N, Bertin B, Bigot C, Calvet A, Chan K, Durand C, Fesquelle V, Feru F, Gilbertsen R, Jacobelli H, Kebsi A, Lallier E, Maignel J, Martin B, Milano S, Ouagued M, Pascal Y, Pruniaux M P, Puaud J, Rocher M N, Terrasse C, Wriggleworth R & Doberty A M, Synthesis, Structure-activity relationships, and pharmacological profile of 9-amino-4-oxo-1-phenyl-3,4,6,7-tetrahydro[1,4]diazepino [6,7,1-hi]indoles:Discovery of potent, selective Phosphodiesterase 4 inhibitors, J Med Chem, 43 (2000) 4850.
7. Cavalla D & Frith R, Phosphodiesterase IV Inhibitors: Structural Diversity and Therapeutic Potential in Asthma, Curr Med Chem, 2 (1995) 561.
8. Dal Piaz V & Giovannoni M P, Phosphodiesterase 4 inhibitors, structurally unrelated to Rolipram, as promising agents for the treatment of asthma and other pathologies, Eur J Med Chem, 35 (2000) 463.
9. Beavo J A, Cyclic nucleotide Phosphodiesterases: Functional implications of multiple forms, Physiol Rev, 75 (1995) 725.
10. Mey M V, Hatzelmann A, Laan I J V, Sterk G J, Thibaut U & Timmerman H, Novel selective PDE4 inhibitors. 1. Synthesis structure-activity relationships, and molecular modeling of 4-(3,4-Dimethoxyphenyl)-2-H-phthalazin-1-ones and analogues, J Med Chem, 44 (2001) 2511.
11. Whelan C J, Prospects for the development of new drugs for the therapy of respiratory diseases, Drugs Today 32 (1996) 295.
12. Raeburn D & Karlsson J A, Phosphodiesterase inhibitors: knckout drops?, J Pharm Pharmacol, 49 (1997) 19.
13. McFadden Jr. E R & Gilbert I A, Asthma, N Engl J Med, 327 (1992) 1928.
14. Barnes P J, New drugs for asthma, Eur Respir J, 5 (1992) 1126.
15. nd ed, (Pharmaceutical Press, London) 1999, 745.
16. 2-adrenoceptor agonists (antiasthmatics-1), Indian Drugs, 35 (1998) 606.
17. Jindal D P, Minu M & Chattopadhaya R, Methylxanthines for asthma therapy (antiasthmatics-2), Indian Drugs, 37 (2000) 1.
18. Torphy T J, Livi G P & Christensen S B, Novel Phosphodiesterase inhibitors for the therapy of asthma, Drug News Perspect, 6 (1993) 203.
19. Raeburn D, Souness J E, Tomkinson A & Karlsson J A, Isozyme selective cyclic nucleotide Phosphodiesterase inhibitors: biochemistry, pharmacology and therapeutic potential in asthma, Prog Drug Res. 40 (1993) 9.
20. Christensen S B & Torphy T J, Isozyme selective Phosphodiesterase inhibitors as antiasthmatic agents, Ann Rep Med Chem, 29 (1994) 185.
21. Soderling S H, Bayuga S J & Beavo J A, Cloning and characterization of cAMP-specific cyclic nucleotide phosphodiesterase, Proc Natl Acad Sci, USA, 95 (1998) 8991.
22. Burnouf C, Pruniaux M P, Szilagyi C M & Bristol J A, Phosphodiesterases 4 inhibitors, Annu Rep Med Chem, 33 (1998) 91.
23. de Boer J, Philpott A J, van Amsterdam R G M, Shahid M, Zaagsma J & Nicholson C D, Human bronchial cyclic nucleotide Phosphodiesterase isozymes: biochemical and pharmacological analysis using selective inhibitors, Br J Pharmacol, 106 (1992) 1028.
24. Gantner F, Kupferschmidt R, Schudt C, Wendel A & Hatzelmann A, In vitro differentiation of human monocytes to macrophages: Change of PDE profile and its relationship to suppression of tumour necrosis factor -alpha release by PDE inhibitors, Br J Pharmacol, 121 (1997) 221.
25. Teixeira M M, Gristwood R W, Copper N & Hellewell P G, Phosphodiesterase (PDE)4 inhibitors: anti-inflammatory drugs of the future?, Trends Pharmacol Sci, 18 (1997) 164.
26. Ukita T, Sugahara M, Terakawa Y, Kuroda T, Wada K, Nakata A, Ohmachi Y, Kikkawa H, Ikezawa K & Naito K, Novel, potent and selective Phosphodiesterase- 4 Inhibitors as antiasthmatic agents: synthesis and biological activities of a series of 1-pyridylnaphthalene derivatives, J Med Chem, 42 (1999) 1088.
27. Christensen S B, Guider A, Forster C J, Gleason J G, Bender P E, Karpinski J M, Dewolf Jr W E, Barnette M S, Underwood D C, Griswold D E, Cieslinski L B, Burman M, Bochnowicz S, Osborn R R, Manning C D, Grous M, Hillegas L M, Bartus J O L, Ryan M D, Eggleston D S, Haltiwanger R C & Torphy T J, 1,4-Cyclohexanecarboxylates; Potent and Selective inhibitors of Phosphodiesterase 4 for the treatment of asthma, J Med Chem, 41 (1998) 821.
28. Torphy T J, Stadel J M, Burman M, Cieslinski L B, McLaughdin M M, White J R & Livi G P, Coexpression of human cAMP-specific Phosphodiesterase activity and high affinity roilpram binding in yeast, J Biol Chem, 267 (1992) 1798.
29. m cyclic AMP phosphodiesterase inhibition in tracheal relaxation and bronchodilation in the guinea pig, J Pharmacol Exp Ther, 251 (1989) 199.
30. 3H]Rolipram binding activity and their relationship to emetic behaviour in the ferret, J Med Chem, 39 (1996) 120.
31. Hulme C, Moriarty K, Miller B, Mathew R Ramanjulu M, Railcox Souness J, Page K M, Uhl J, Travis J, Huang F, Labaudiniere R & Djuric S W; The synthesis and biological evaluation of a novel series of Indole PDE4 inhibitors 1, Bioorg Med Chem Lett, 8 (1998) 1867.
32. Torphy T J & Undem B J, Phosphodiesterase inhibitors : new opportunities for the treatment of asthma, Thorax, 46 (1991) 512.
33. He W, Huang F-C, Hanney B, Souness J, Miller B, Liang G, Mason J & Djuric S, Novel cyclic compounds as potent Phosphodiesterase 4 inhibitors, J Med Chem, 41 (1998) 4216.
34. Bacher E, Boer C, French B K, Demnitz F W J, Keller T H, Mazzoni L, Miiller T & Walker C, N-aryl roilpram derivatives as potent and selective PDE4 inhibitors, Bioorg Med Chem Lett, 8 (1998) 3229.
35. Hulme C, Poli G B, Huang F C, Souness J E & Djuric S W, Quaternary substituted PDE4 inhibitors I: The synthesis and in vitro evaluation of a novel series of oxindoles, Bioorg Med Chem Lett, 8 (1998) 175.
36. Regan J, Bruno J, McGary D, Polic G, Henney B, Bower S, Travis J, Sweeney D, Miller B, Souness J & Djuric S, 2-Substituted- 4-methoxybenzimidazole-based PDE4 inhibitors, Bioorg Med Chem Lett, 8 (1998) 2737.
37. Silvestre J, Graul A & Castaner J, SB-207499, Antiasthmatic/antiinflammatort phosphodiesterase IV inhibitors, Drug Future, 23 (1998) 607.
38. 38 Marivet M C, Bourguignon J J, Lugnier C, Mann A, Stoclet J C & Wermuth C G, Inhibition of cyclic adenosine-3',5'-phosphate phosphodiesterase from vascular smooth muscle byrolipram analogues, J Med Chem, 32 (1989) 1450.
39. Marx D, Poppe H & Szelenyi I, The in vivo activity of AWD-12-281, a potent PDE inhibitor for the treatment of allergic asthma, J Allergy Clin Immunol, 103 (1999) S127.
40. Wilhelm R S, Chin R L, Devens B H & Alvarez R, Pyrido[2,3-d]pyrimidinone phosphodiesterase inhibitors, Int Pat Appl, WO 93/19068; Chem Abstr, 120 (1994) 164213.
41. Wilhelm R, Loe B, Alvarez R, Devens B & Fong A, Pyrido[2,3-d]pyridazinones as potent and selective type 4 phosphodiesterase inhibitors, RSC-SCI, Med Chem Symp. Cambridge, United Kingdom (1995) 32.
42. Dal Piaz V, Giovannoni M P, Castellana C, Palacios J M, Beleta J, Domenech T & Segarra V, Novel heterocyclicfused pyridazinones as potent and selective Phosphodiesterase IV inhibitors, J Med Chem, 40 (1997) 1417.
43. Dal Piaz V, Giovannoni M P, Castellana C, Palacios J M, Beleta J, Domenech T & Segarra V, Heterocyclic-fused 3(2H -pyridazinones as potent and selective PDE IV inhibitors: further structure-activity relationships and molecular modeling studies, Eur J Med Chem, 33 (1998) 789.
44. Suzuki F, Kuroda T, Kawanita T, Manabe H, Kitamura S, Ohmori K, Ichimura M, Kase H & Ichikawa S, New bronchodilators. 3. Imidazo[4,5-c][1,8]naphthyridin-4(5H)-ones, J Med Chem, 35 (1992) 4866.
45. 3H]roliOpram binding, J Med Chem, 34 (1991) 86.
46. Shimazaki N, Watanabe S, Sawada A & Hemmi K, Preration of pyrido[2,3-b]pyrazin-4-one inhibitors of phosphodiesterase 4 and tumor necrosis factor, United Kingdom Pat Appl, GB-2291422 1996; Chem Abstr, 125 (1996) 10857.
47. Shimazaki N, Sawada A & Watanabe S, Preration of pyrido[2,3-b]pyrazines as inhibitors of phosphodiesterase 4 and tumor necrosis factor production, Int Pat Appl WO 97/24355; Chem Abstr, 127 (1997) 14915.
48. Beasley S C, Cooper N, Gowers, Gregory, Gregory J P, Haughan A F, Hellewell P G, Macari D, Miotla J, Montana J G, Morgan T, Naylor R, Runcie K A, Tuladhar B & Warneck J B, Synthesis and evaluation of a novel series of phosphodiesterase 4 inhibitors. A potential treatment for asthma, Bioorg Med Chem Lett, 8 (1998) 2629.
49. Dyke H J, Montana J G, Lowe C, Kendall H J, Hamnah J & Sabin V M, Preparation of quinoline carboxamides as tumor necrosis factor (TNF) inhibitors and as phosphodiesterase (PDE)-4 inhibitors, Int Pat Appl, WO 97/44036, 1998; Chem Abstr, 128 (1999) 48146.
50. Jindal D P, Bhatti R S, Ahlawat S & Gupta R, Synthesis and bronchodilatory activity of some nitrogen bridgehead compounds, Eur J Med Chem, 37 (2002) 419.
51. Suzuki F, Kuroda T, Hayashi H, Nakasato Y, Manabe H, Ohmori K & Kitamura S, New bronchodilators. 11, 3H-imidazo [4,5-c]quinoline-4(5H)-ones, Chem Pharm Bull, 40 (1992) 3245.
52. Crespo M I, Pages L, Vega A, Segarra V, Lopez M, Domenech T, Miralpeix M, Beleta J, Ryder H & Palacios J M, Design, synthesis and biological activities of new thieno[3,2-d]pyrimidines as selective type 4 phosphodiesterase inhibitors, J Med Chem, 41 (1998) 4021.
53. Merz K H, Marko D, Regiert T, Reiss G, Frank W & Eisenbrand G, Synthesis of 7-benzylamino-6-chloro-2-piperazino- 4-pyrrolidinopteridine and novel derivatives free of positional isomers. Potent inhibitors of cAMP-specific phosphodiesterase and of malignant tumor cell growth, J Med Chem, 41 (1998) 4733.
54. Trifilieff A, Wyss D, Walker C, Mazzoni L & Hersperger R, Pharmacological profile of a novel phosphodiesterase 4 inhibitor, 4-(8-benzo[1,2,5]oxadiazol-5-yl-[1,7] naphthyridin-6-yl]-benzoic acid (NVP-ABE171), a 1,7-naphthyridine derivative, with anti-inflammatory activities, J Pharmacol Exp Ther, 301 (2002) 241.
55. Iwasaki T, Kondo K, Kuroda T, Moritani Y, Yamagata S, Sugiura M, Kikkawa H, Kaminuma U & Ikezawa K, Novel selective PDE IV inhibitors as antiasthmatic agents. Synthesis and biological activities of a series of 1-aryl-2-3-bis (hydroxymethyl)naphthalene lignans, J Med Chem, 39 (1996) 2696.
56. Macdonald D, Perrier H, Liu S, Laliberte' F, Rasori R, Robichaud A, Masson P & Huang Z, Hunting the emesis and efficacy targets of PDE4 inhibitors: identification of the photoaffinity probe 8-(3-azidophenyl)-6-[(4-iodo-1H-1-imidazolyl) methyl)quinoline (APIIMQ), J Med Chem, 43 (2000) 3820.
57. Barnes P J, Cyclic nucleotides and Phosphodiesterases and airway function, Eur Respir J, 8 (1995) 457.
58. Vassallo R & Lipsky J J, Theophylline: recent advances in the understanding of its mode of action and uses in clinical practice, Mayo Clin Proc, 73 (1998) 346.
59. Persson C G A, Overview of effects of theophylline, J Allergy Clin Immunol, 78 (1986) 780.
60. Miyamoto K, Kurita M, Ohmae S, Sakai R, Sanae F & Takagi K, Selective tracheal relaxation and phosphodiesterase-4 inhibition by xanthine derivatives, Eur J Pharmacol, 267 (1994) 317.
61. Sawanishi H, Suzuki H, Yamamoto S, Waki Y, Kasugai S, Ohya K, Suzuki N, Miyamoto K & Takagi K, Selective inhibitors of cyclic AMP-specific phosphodiesterase heterocycle-condensed purines, J Med Chem, 40 (1997) 3248.
62. Wells J N, Garst J E & Kramer G L, Inhibition of separated forms of cyclic nucleotide Phosphodiesterase from pig coronary arteries by 1,3-disubstituted and 1,3,8-trisubstituted xanthines, J Med Chem, 24 (1981) 954.
63. Shahid M, van Amsterdam R G M, de Boer J, ten Berge R E, Nicholson C D & Zaagsma J, The presence of five cyclic nucleotide phosphodiesterase isozyme activities in bovine tracheal smooth muscle and the functional effects of selective inhibitors, Br J Pharmacol, 104 (1991) 471.
64. Nicholson C D, Jackman S A & Wilke R, The ability of denbufylline to inhibit cyclic nucleotide phosphodiesterase and its affinity for adenosine receptors and the adenosine re-uptake site, Br J Pharmacol, 97 (1989) 889.
65. Ferrer L, Alberola J, Queralt M, Brazis P, Rabanal R, Llenas J, Puiqdemont A, Clinical anti-inflammatory efficacy of arofylline, a new selective phosphodiesterase - 4 inhibitors, in dogs with atopic dermatitis, Vet Rec, 145 (1999) 191.
66. Buckle D R, Arch J R S, Connolly B J, Fenwick A E, Foster K A, Murray K J, Readshaw S A, Smallridge M & Smith D G, Inhibition of cyclic nucleotide Phosphodiesterase by derivatives of 1,3-bis(cyclopropylmethyl)xanthine, J Med Chem, 37 (1994) 476.
67. Ragnier G L, Guillonneau C G, Duhault J L, Tisserand F P, Saint-Romas G & Holstorp S M, New xanthine derivatives with potent and long lasting anti-bronchoconstrictive activity, Eur J Med Chem, 22 (1987) 243.
68. Cavalla D, Hofer P, Gehrige A & Wintergest P, Preparation of purines, isoguanines and dithioxanthines as phosphodiesterase-4 inhibitors, Int Pat Appl. WQ 95/00516 1995; Chem Abstr, 122 (1995) 239459.
69. Kawasaki A, Hoshino K, Osaki R, Mizushima Y & Yano S, Effect of ibudilast: a novel antiasthmatic agent, on airway hypersensitivity in bronchial asthma, J Asthma 29 (1992) 245.
70. Cortijo J, Pons R, Dasi F, Martin N, Martinez-Losa M, Advenier C & Morcillo E J, Bronchodilator and anti-inflammatory activities of SCA40: Studies in human isolated bronchus, human eosinophils, and in the guinea-pig in vivo, Naunyn-Schmiedeberg's Arch Pharmacol, 356 (1997) 806.
71. Davies G E, Antibronchoconstriction activity of two new phosphodiesterase inhibitors, a triazolopyrazine (ICI 58301) and triazolopyrimidine (ICI 63197), J Pharm Pharmacol, 25 (1973) 681.
72. Cavalla D & Gale D, A Case History of Successful Virtual Research, Drug News Perspect, 10 (1997) 470.
73. Norman P, PDE4 inhibitors 1998, Exp Opin Ther Patents, 8 (1998) 771.
74. Marfat A, Preparation of indazole derivatives as inhibitors of phosphodiesterase 4 and tumor necrosis factor production, Int Pat Appl, WO 98/09961; Chem Abstr, 128 (1999) 217368.
75. Duplantier A J, Andresen C J, Cheng J B, Cohan V L, Decker C, DiCapua F M, Kraus K G, Johnson K L, Turner C R, UmLand J P, Watson J W, Wester R T, Williams A S & Willaims J A, 7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c] pyridines as novel inhibitors of human eosinofil phosphodiesterase, J Med Chem, 41 (1998) 2268.
76. Pascal Y, Andrianjara C R, Auclair E, Avenel N, Bertin B, Calvet A, Feru F, Lardon S, Moodley I, Ouagued M, Payne A, Pruniaux M P & Szilagyi C, Synthesis and structure activity relationships of 4-oxo-1-phenyl-3,4,6,7-tetrahydro-[1,4]-diazepino [6,7,1-hi]indoles, Bioorg Med Chem, 10 (2000) 35.