Pyrazolo[3,4-B]pyridine compounds, and their use as phosphodiesterase inhibitors

1 1-41-3222 13a 1-33 3-63-85-71 2 24The invention relates to a compound of formula (I) or a salt thereof: wherein: Ris Calkyl, Cfluoroalkyl or -(CH)OH; Ris a hydrogen atom (H), methyl or Cfluoroalkyl; Ris a hydrogen atom (H) or Calkyl; Ris optionally substituted branched Calkyl, optionally substitut...

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Main Authors Allen, David George, Coe, Diane Mary, Cook, Caroline Mary, Cooper, Anthony William James, Dowle, Michael Dennis, Edlin, Christopher David, Hamblin, Julie Nicole, Johnson, Martin Redpath, Jones, Paul Spencer, Lindvall, Mika Kristian, Mitchell, Charlotte Jane, Redgrave, Alison Judith
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Published 05.05.2009
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Abstract 1 1-41-3222 13a 1-33 3-63-85-71 2 24The invention relates to a compound of formula (I) or a salt thereof: wherein: Ris Calkyl, Cfluoroalkyl or -(CH)OH; Ris a hydrogen atom (H), methyl or Cfluoroalkyl; Ris a hydrogen atom (H) or Calkyl; Ris optionally substituted branched Calkyl, optionally substituted Ccycloalkyl, optionally substituted mono-unsaturated-Ccycloalkenyl, optionally substituted phenyl, or an optionally substituted heterocyclic group of sub-formula (aa), (bb) or (cc): in which nand nindependently are 1 or 2; and Y is O, S, SO, or NR; and wherein Het is of sub-formula (i), (ii), (iii), (iv) or (v): The compounds are phosphodiesterase (PDE) inhibitors, in particular PDE4 inhibitors. Also provided is the use of a compound of formula (I), or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the treatment and/or prophylaxis of an inflammatory and/or allergic disease in a mammal such as a human, for example chronic obstructive pulmonary disease (COPD), asthma, or allergic rhinitis.
AbstractList 1 1-41-3222 13a 1-33 3-63-85-71 2 24The invention relates to a compound of formula (I) or a salt thereof: wherein: Ris Calkyl, Cfluoroalkyl or -(CH)OH; Ris a hydrogen atom (H), methyl or Cfluoroalkyl; Ris a hydrogen atom (H) or Calkyl; Ris optionally substituted branched Calkyl, optionally substituted Ccycloalkyl, optionally substituted mono-unsaturated-Ccycloalkenyl, optionally substituted phenyl, or an optionally substituted heterocyclic group of sub-formula (aa), (bb) or (cc): in which nand nindependently are 1 or 2; and Y is O, S, SO, or NR; and wherein Het is of sub-formula (i), (ii), (iii), (iv) or (v): The compounds are phosphodiesterase (PDE) inhibitors, in particular PDE4 inhibitors. Also provided is the use of a compound of formula (I), or a pharmaceutically acceptable salt thereof, in the manufacture of a medicament for the treatment and/or prophylaxis of an inflammatory and/or allergic disease in a mammal such as a human, for example chronic obstructive pulmonary disease (COPD), asthma, or allergic rhinitis.
Author Hamblin, Julie Nicole
Cooper, Anthony William James
Lindvall, Mika Kristian
Mitchell, Charlotte Jane
Johnson, Martin Redpath
Redgrave, Alison Judith
Dowle, Michael Dennis
Edlin, Christopher David
Cook, Caroline Mary
Allen, David George
Coe, Diane Mary
Jones, Paul Spencer
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References (WO-02/098878) 20021200
Hoehn et al. (3833594) 19740900
Montana et al., Annual Reports in Medicinal Chemistry, 2001, vol. 36, pp. 41-56.
Ochiai H. et al.; New orally active PDE4 inhibitors with therapeutic potential; Bioorg. Med. Chem.; 2004 (stated to have been available online Jun. 20, 2004); 12(15); pp. 4089-4100.
Yu G., Mason H.J., et. al.; Substituted pyrazolopyridines as potent and selective PDE5 inhibitors: potential agents for treatment of erectile disfunction; Journal of Medicinal Chemistry; 2001; 44; pp. 1025-1027.
Ochiai H. et al.; Bioorg. Med. Chem. Web Release; 2003.
De Mello, A. Echevarria, et al.; Antileishmanial Pyrazolopyridine Derivatives: Synthesis and Structure-Activity Relationship Analysis; Journal of Medicinal Chemistry; 2004; 47(22); pp. 5427-5432.
(WO-03/016563) 20030200
Dow et al. (5593997) 19970100
Chemical Abstracts Registry-CAS registry No. 502143-17-1 which has the laboratory code NSC 235755, Apr. 8, 2003.
Hohn H et al: Potential Antidiabetic Agents. Pyrazolo63,4-b!pyridinesW Journal of Medicinal Chemistry, American Chemical Society. Washington, US, vol. 16, No. 12, 1973, pp. 1340-1346, XP002097814 ISSN: 0022-2623 p. 1343; compound 37.
U.S. Appl. No. 10/598,838, filed Mar. 2005, Christensen, IV.
Giembycz M.A.; Phosphodiesterase 4 Inhibitors and the Treatment of Asthma: Where Are We Now and Where Do We Go from Here?; Drugs; 2000; 59(2); pp. 193-212.
Denzel et al. (3833598) 19740900
Hoehn et al. (3979399) 19760900
Patel J.B. and Malick J.B.; Pharmacological properties of tracazolate: a new non-benzodiazepine anxiolytic agent; Eur. J. Pharmacol.; 1982; 78; pp. 323-333.
U.S. Appl. No. 10/598,973, filed Mar. 2005, Cook, et al.
Shi D., et al.; Pyrazolopyridines: effect of structural alterations on activity at adenosine- and GABA-A receptors; Drug Development Research; 1997; 42; pp. 41-56.
Patel J.B., et al.; "Pharmacology of pyrazolopyridines"; Pharmacology Biochemistry & Behaviour; 1985; vol. 23; pp. 675-680.
Ochiai H. et al.; Discovery of new orally active phosphodiesterase (PDE4) inhibitors; Chem. Pharm. Bull.; 2004 (stated to have been published online Jun. 15, 2004); 52(9); pp 1098-1104.
Daly J. W. et al.; 1-methyl-4-substituted-1H-pyrazolo [3,4-b] pyridine-5-carboxylic acid derivatives: effect of structural alterations on activity at A1 and A2 adenosine receptors; Medicinal Chemistry Research; 1994; 4(5); pp. 293-306; Birkhaeuser; Boston US.
Glass II, W. F., et al.; "Inhibition of human lung cyclic GMP and cyclic AMP phosphodiesterases by certain nucleosides, nucleotides, and pharmacological phosphodiesterase inhibitors"; Biochemical Pharmacology; 1979; 28; pp. 1107-1112.
Sabitha, et al.; A Facile Route to Pyrazolo[3,4-b]Pyridines and [1]Benzopyrano[4′,3′-e]Pyrazolo[3,4-b]Pyridines; Indian Institute of Chemical Technology; 1999; 29(4),655-665; Synthetic Communications; India.
Hoehn et al. (3856799) 19741200
Hoehn et al. (3755340) 19730800
Allen et al. (2006/0089375) 20060400
(0 180 318) 19860500
Hoen et al. (3840546) 19741000
(WO-01/44244) 20010600
Davis A., et al.,; "Strategic approaches to drug design. II. Modelling studies on phosphodiesterase substrates and inhibitors"; Journal of Computer-Aided Molecular Design; 1987; 1; pp. 97-119.
Schweighoffer et al. (2005/0043319) 20050200
(WO-2005/090353) 20050900
(WO-2005/058892) 20050600
Hoehn et al. (4115394) 19780900
Denzel TH.; (translation of title: New Synthesis of 1-Unsubstituted 1H-Pyrazolo [3.4-b] Pyridine-5-Carboxylic Acid Esters); Archiv der Pharmazie; 1974; 307(3); pp. 177-186.
Ochiai H. et al.; New orally active PDE4 inhibitors with therapeutic poteintial; Bioorg. Med. Chem. Lett.; Jan. 5, 2004 issue (available as "articles in press" version on or before Dec. 4, 2003, possibly Oct. 2003, via internet); 14(1); pp. 29-32.
Bondavalli F. et al; Synthesis, molecular modelling studies, and pharmacological activity of selective A1 receptor antagonists; Journal of Medicinal Chemistry; 2002; 45(22); pp. 4875-4887.
Hoehn et al. (3925388) 19751200
Hoehn H. et al.; 1H-pyrazolo[3,4-b]pyridines; Journal of Heterocyclic Chemistry; 1972; 9(2); pp. 235-253.
(WO-02/060900) 20020800
(151 1006) 19750400
Hoehn et al. (3966746) 19760600
(WO-2004/024728) 20040300
Beer B., et al.; "Enhancement of 3H-diazepam binding by SQ 65,396: a novel anti-anxiety agent"; Pharmacology Biochemistry & Behaviour; 1978; 9; pp. 849-851.
(1003419) 19770100
Kripalani K. J. et al.; "Biotransformation in the monkey of cartazolate (SQ 65,396), a substituted pyrazolopyridine having anxiolytic activity"; Xenobiotica; 1981; 11(7); pp. 481-488.
(WO-02/081463) 20021000
Chakravorti; Synthesis of Some Isoquinolylpyrazolo[3,4-b]pyridine Derivatives as Possible Antifilarial Agents; Indian J. Chem.; Feb. 1978; vol. 16B, pp. 161-163.
(WO-2005/090348) 20050900
Chasin M., et al.; "1-Ethyl-4-(isopropylidenehydrazino)-1H-pyrazolo-(3,4-b)-pyridine-5-carboxylic acid, ethyl ester, hydrochloride (SQ 20009)-a potent new inhibitor of cyclic 3′,5′-nucleotide phosphodiesterases"; Biochemical Pharmacology; 1972; 21; pp. 2443-2450.
Bare T.M. et al.; Synthesis and structure-activity relationships of a series of anxioselective pyrazolopyridine ester and amide anxiolytic agents; Journal of Medicinal Chemistry; 1989; 32; pp. 2561-2573.
(WO 00/15222) 20000300
(WO-2004/056823) 20040700
Allen et al. (2006/0252790) 20061100
Schenone S. et al.; Synthesis and biological data of 4-amino-1-(2-chloro-2-phenylethyl)-1H-pyrazolo[3,4-b]pyridine-5-carboxylic acid ethyl esters, a new series of A1-adenosine receptor (A1AR) ligands; Bioorg. Med. Chem. Lett.; 2001; 11; pp. 2529-2531.
(141 7489) 19731200
(553 799) 19740900
(WO-01/23389) 20010400
Polson J. B., et al.; "Analysis of the relationship between pharmacological inhibition of cyclic nucleotide phosphodiesterase and relaxation of canine tracheal smooth muscle"; Biochemical Pharmacology; 1979; 28; pp. 1391-1395 RBI 1998, Catalogue No. T-112, Tracazolate; 1998; p. 340.
Weinryb I., et al.; "Studies in vitro and in vivo with SQ-20,009: an inhibitor of cyclic nucleoside phosphodiesterase with central nervous system activity"; Excerpta Med. Int. Congr. Ser.; 1975; 359; pp. 857-865.
Allen et al. (2007/0111995) 20070500
Horowitz Z. P., et al.; "Cyclic AMP and anxiety"; Psychosomatics; 1972; vol. XIII, No. 2; pp. 85-92.
(0 076 035) 19830400
(WO-00/15222) 20000300
(2002-020386) 20020100
(WO-2005/090354) 20050900
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Title Pyrazolo[3,4-B]pyridine compounds, and their use as phosphodiesterase inhibitors
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