Process for the preparation of chemical compounds

Details Process for the preparation of chemical compounds Process for the preparation of chemical compounds

2002-10-25

2004-06-29

Morris, Patricia L. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

Reexamination Certificate

active

06756498

ABSTRACT:

BACKGROUND OF THE INVENTION
This invention relates to a process for the preparation of pyrazolopyridine derivatives.
Pyrazolopyridine derivatives of formula (Ia)
and pharmaceutically acceptable derivatives thereof in which:
R
0a
and R
1a
are independently selected from H, halogen, C
1-6
alkyl, C
1-6
alkoxy, or C
1-6
alkoxy substituted by one or more fluorine atoms;
R
2a
is H, C
1-6
alkyl, C
1-6
alkyl substituted by one or more fluorine atoms, C
1-6
alkoxy, C
1-6
hydroxyalkyl, SC
1-6
alkyl, C(O)H, C(O)C
1-6
alkyl, C
1-6
alkylsulphonyl, C
1-6
alkoxy substituted by one or more fluorine atoms; and
R
3a
is C
1-6
alkyl or NH
2
;
are disclosed in WO 00/26216 (Glaxo Group Limited), unpublished at the priority date of the instant application.
Pyrazolopyridine derivatives of formula (Ib)
and pharmaceutically acceptable derivatives thereof in which:
R
0b
and R
1b
are independently selected from H, halogen, C
1-6
alkyl, C
1-6
alkoxy, or C
1-6
alkoxy substituted by one or more fluorine atoms;
R
2b
is halogen, CN, CONR
4b
R
5b
, CO
2
H, CO
2
C
1-6
alkyl, or NHSO
2
R
4b
;
R
3b
is C
1-6
alkyl or NH
2
; and
R
4b
and R
5b
are independently selected from H, C
1-6
alkyl, phenyl, phenyl substituted by one or more atoms or groups (selected from halogen, C
1-6
alkyl, C
1-6
alkoxy, or C
1-6
alkoxy substituted by one or more fluorine atoms), or together with the nitrogen atom to which they are attached form a saturated 4 to 8 membered ring;
are disclosed in WO 00/52008 (Glaxo Group Limited), also unpublished at the priority date of the instant application.
As described in WO 00/26216 and WO 00/52008, the compounds of formulae (Ia) and (Ib) are potent and selective inhibitors of COX-2 and, as such, are of use in human and veterinary medicine, particularly in the treatment of the pain (both chronic and acute), fever and inflammation of a variety of conditions and diseases. Such conditions and diseases are well known in the art and include arthritis, such as rheumatoid arthritis; and degenerative joint diseases, such as osteoarthritis.
Several processes for the preparation of the compounds of formulae (Ia) and (Ib) are respectively disclosed in WO 00/26216 and WO 00/52008, inter alia the thermal rearrangement of an azirine in 1,2,4-trichlorobenzene at reflux.


REFERENCES:
patent: 3718656 (1973-02-01), Okamoto et al.
patent: 4985444 (1991-01-01), Shiokawa et al.
patent: 5155114 (1992-10-01), Shiokawa et al.
patent: 5296490 (1994-03-01), Shiokawa et al.
patent: 5300478 (1994-04-01), Michaely et al.
patent: 5498774 (1996-03-01), Mitsudera et al.
patent: 5552422 (1996-09-01), Gauthier et al.
patent: 5700816 (1997-12-01), Isakson et al.
patent: 5990148 (1999-11-01), Isakson et al.
patent: 6136839 (2000-10-01), Isakson et al.
patent: 0364204 (1990-04-01), None
patent: 0379979 (1990-08-01), None
patent: 0404190 (1990-12-01), None
patent: 0467248 (1992-01-01), None
patent: 91/00092 (1991-01-01), None
patent: 91/19497 (1991-12-01), None
patent: 95/00501 (1995-01-01), None
patent: 96/06840 (1996-03-01), None
patent: 96/21667 (1996-07-01), None
patent: 96/31509 (1996-10-01), None
patent: 96/41625 (1996-12-01), None
patent: 96/41626 (1996-12-01), None
patent: 96/41645 (1996-12-01), None
patent: 99/12930 (1999-01-01), None
patent: 01/14375 (2002-03-01), None
patent: 02/066481 (2002-08-01), None
Benincori, Tiziana et al., “Studies on Wallach's imidazole synthesis,”J. Chem. Soc., Perkin Trans 1, (1993) vol. 6, pp. 675-679.
S. Gunzenhauser et al., “Synthese substituierter 6H-Chromeno 4,3-b! indolizine dn ihrer Aza-analogen,”Helvetica Chimica Acta, vol. 68, 1985, pp. 56-63.
Talley, John J.,Ashley Publications Ltd., ISSN 1354-3776, 7(1): (1997), pp. 55-62.
Talley, John J.,Progress in Medicinal Chemistry, vol. 36, (1999): pp. 201-234.
Carter, Jeffery S.,Ashley Publications Ltd., ISSN 1354-3776, vol. 8(1): (1998), pp. 21-29.
Vane, John,Nature, vol. 367: (1994) pp. 215-216.
Roy, P., “A New Series of Selective Cox-2 Inhibitors: 5,6-Diarylthiazolo [3,2-b][1,22,4] Triazoles,”Bioorganiz&Med. Chem. Ltrs., vol. 7, No. 1, 1997, pp. 57-62.
Therien, Michael, Synthesis and Biological Evaluation of 5, 6-Diarylimidazo[2.1-b]Thiazole As Selective Cox-2 Inhibitors,Bioorganic&Med. Chem. Ltrs., vol. 7, No. 1, 1997, pp. 47-52.
Akahane, Atsushi, “Discovery of 6-Oxo-3-(2-Phenlypyrazolo[1,5-a]pyridin-3-yl)-1(6H)-pyridazinebutanoic Acid (FR 838): A Novel Xanthine Adenosine A1Receptor Antagonist with Potent Diuretic Activity,”Journal of Medicinal Chemistry, vol. 42, No. 5, 1999, pp. 779-783.

Affiliated with

Also associated with

Rating

Process for the preparation of chemical compounds does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for the preparation of chemical compounds, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the preparation of chemical compounds will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3362070