Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Reexamination Certificate
1998-07-01
2003-01-14
Rotman, Alan L. (Department: 1612)
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
C546S093000
Reexamination Certificate
active
06506767
ABSTRACT:
BACKGROUND OF THE INVENTION
This invention relates to crystalline polymorphs of 8-chloro-6,11-dihydro-11-(4-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine (hereinafter “descarbonylethoxyloratadine”) represented by the formula
pharmaceutical compositions containing such polymorphs, and methods of using such polymorphs to treat allergic reactions in mammals.
U.S. Pat. No. 4,659,716 discloses descarbonylethoxyloratadine which possesses antihistaminic properties with substantially no sedative properties. This U.S. Patent also discloses methods of making descarbonylethoxyloratadine and using it to treat allergic reactions in mammals.
To prepare pharmaceutical compositions containing descarbonylethoxyloratadine for administration to mammals in accordance with exacting health registration requirements of the U.S. and international health registration authorities, e.g. the FDA's Good Manufacturing Practices(“GMP”)requirements, there is a need to produce descarbonylethoxyloratadine in as pure a form as possible, especially a form having constant physical properties.
SUMMARY OF THE INVENTION
We have discovered that descarbonylethoxyloratadine can exist in the form of two distinct crystalline polymorphs, each having distinctly different physical properties.
Accordingly, this invention provides crystalline polymorph form 1 descarbonylethoxyloratadine essentially free of polymorph form 2 and characterized by the following x-ray powder diffraction pattern having characteristic peaks expressed in terms of “d” spacing and relative intensities(“RI”) at approximately:
d spacing (±0.04)
RI
9.04
Weak
6.42
Weak
5.67
Weak
5.02
Weak
3.58
Weak
This invention also provides crystalline polymorph form 1 descarbonylethoxyloratadine essentially free of polymorph form 2 and characterized by the following x-ray powder diffraction pattern essentially free of poymorph form 2 and having characteristic peaks expressed in terms of “d” spacings and relative intensities (“RI”)(s=strong, m=medium, w=weak, v=very and d=diffuse) at approximately:
d spacing
RI
9.04
W
7.24
M
7.11
VWD
6.69
M
6.42
W
6.02
W
5.84
VW
5.67
W
5.02
W
4.73
M
4.54
W
4.48
W
4.40
M
4.29
WD
4.25
W
4.18
VS
3.72
W
3.68
W
3.63
W
3.58
W
3.52
M
3.45
W
3.37
S
3.23
W
3.19
M
3.14
VWD
3.10
VWD
3.04
M
2.99
VWD
2.93
VWD
2.87
VWD
2.84
W
2.79
VWD
2.73
VWD
2.70
VWD
2.65
W
2.57
VWD
2.56
VWD
2.55
VWD
2.51
VWD
2.48
VWD
2.47
VWD
2.44
VWD
2.42
WD
2.37
VWD
2.34
WD
2.32
WD
2.29
VWD
2.27
W
This invention further provides crystalline polymorph form 2 descarbonylethoxyloratadine substantially free of poymorph form 1 and characterized by the following x-ray powder diffraction pattern having characteristic peaks expressed in terms of “d” spacing and relative intensities(“RI”) approximately:
d spacing (+ 0.04)
RI
8.34
Weak
6.87
Medium
6.20
Medium
4.90
Medium
This invention also provides crystalline polymorph form 2 descarbonylethoxyloratadine substantially free of poymorph form 1 and characterized by the following x-ray powder diffraction having characteristic peaks expressed in terms of “d” spacing and relative intensities (“RI”) s=strong, m=medium, w=weak, v=very and d=diffuse) at approximately:
d spacing
RI
8.34
W
7.21
W
6.87
M
6.75
M
6.20
M
6.04
M
5.91
VW
4.90
M
4.71
M
4.64
M
4.50
WD
4.39
VS
4.34
S
4.19
VWD
4.08
W
3.95
S
3.84
M
3.66
S
3.52
W
3.46
W
3.45
WD
3.39
W
3.25
S
3.18
W
3.11
W
3.07
M
2.95
W
2.88
WD
2.81
WD
2.79
WD
2.72
VW
2.59
VW
2.51
WD
2.45
VWD
2.40
VWD
2.38
VWD
2.32
VWD
2.30
VWD
REFERENCES:
patent: 4282233 (1981-08-01), Villani
patent: 4659716 (1987-04-01), Villani et al.
The Merck Index,Eleventh Edition, p. 877,item No. 5455, 1989.
Eckhart Charles G.
Lee Junning
Mitchell Michael B.
Rogers Lawrence R.
Sawant Naneshwar S.
Hoffman Thomas D.
Rotman Alan L.
Schering Corporation
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