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US 9,133,142 B2Granted
Salts or co-crystals of 3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol
AssigneeGruenenthal GmbH
InventorsMichael Gruss, Magda Kraszewski
Life of this patent
Estimating the term…
Abstract
A salt or cocrystal of 3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol (component a) and at least one acid component (b1) or at least one acid component (b2), wherein the salt or cocrystal of component (a) and component (b2) is present in crystalline and/or amorphous form, a pharmaceutical composition comprising said salt or cocrystal, and a method of treating pain in a subject in need thereof by administering an effective amount of said salt or cocrystal.
Claims17
A salt or cocrystal of
- (a) (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol, and
- (b1) at least one acid selected from the group consisting of embonic acid, (2S,3S)-dibenzoyltartaric acid, sebacic acid, and 1-hydroxy-2-naphthoic acid, or
- (b2) at least one acid selected from the group consisting of nicotinic acid, hydrogen bromide, fumaric acid, and malonic acid
- wherein the salt or cocrystal of component (a) and component (b1) or the salt or cocrystal of component (a) and component (b2) is present in crystalline form, and
- wherein said crystalline form is selected from the group consisting of:
- a salt or cocrystal of embonic acid and (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol having at least one or more X-ray diffraction peaks selected from the group consisting of 7.94±0.20 (2θ), 10.40±0.20 (2θ), 14.25±0.20 (2θ), 17.18±0.20 (2θ) and 18.77±0.20 (2θ) or at least one or more X-ray diffraction peaks selected from the group consisting of 6.00±0.20 (2θ), 11.96±0.20 (2θ) and 17.61±0.20 (2θ);
- a hemi salt or cocrystal of (2S,3S)-dibenzoyltartaric acid and (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol having at least one or more X-ray diffraction peaks selected from the group consisting of 9.35±0.20 (2θ), 12.22±0.20 (2θ), 13.41±0.20 (2θ), 14.00±0.20 (2θ), 17.89±0.20 (2θ), 18.28±0.20 (2θ), 18.73±0.20 (2θ), 19.53±0.20 (2θ), 19.98±0.20 (2θ), 23.19±0.20 (2θ) and 24.33±0.20 (2θ);
- a salt or cocrystal of sebacic acid and (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol having at least one or more X-ray diffraction peaks selected from the group consisting of 12.16±0.20 (2θ), 15.31±0.20 (2θ), 16.88±0.20 (2θ), 18.90±0.20 (2θ), 22.66±0.20 (2θ), 23.08±0.20 (2θ) and 25.46±0.20 (2θ);
- a salt or cocrystal of 1-hydroxy-2-naphthoic acid and (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol having at least one or more X-ray diffraction peaks selected from the group consisting of 13.59±0.20 (2θ), 13.97±0.20 (2θ), 15.36±0.20 (2θ), 18.04±0.20 (2θ), 19.75±0.20 (2θ), 19.98±0.20 (2θ), 20.52±0.20 (2θ), 24.37±0.20 (2θ) and 26.09±0.20 (2θ);
- a salt or cocrystal of nicotinic acid and (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol having at least one or more X-ray diffraction peaks selected from the group consisting of 12.60±0.20 (2θ), 15.61±0.20 (2θ) and 22.82±0.20 (2θ) or at least one or more X-ray diffraction peaks selected from the group consisting of 10.34±0.20 (2θ), 12.14±0.20 (2θ), 22.38±0.20 (2θ), 23.65±0.20 (2θ) and 26.11±0.20 (2θ);
- a salt or cocrystal of hydrobromic acid and (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol having at least one or more X-ray diffraction peaks selected from the group consisting of 9.93±0.20 (2θ), 14.39±0.20 (2θ), 15.22±0.20 (2θ), 17.60±0.20 (2θ), 20.81±0.20 (2θ), 21.61±0.20 (2θ), 24.37±0.20 (2θ), 24.73±0.20 (2θ), 25.19±0.20 (2θ), 27.14±0.20 (2θ), 27.94±0.20 (2θ), 29.00±0.20 (2θ) and 30.75±0.20 (2θ);
- a salt or cocrystal of malonic acid and (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol having at least one or more X-ray diffraction peaks selected from the group consisting of 8.75±0.20 (2θ), 11.85±0.20 (2θ), 13.74±0.20 (2θ), 16.78±0.20 (2θ), 18.09±0.20 (2θ), 19.17±0.20 (2θ), 16.65±0.20 (2θ), 20.45±0.20 (2θ), 21.66±0.20 (2θ), 24.80±0.20 (2θ) and 25.55±0.20 (2θ);
- and
- a hemi salt or cocrystal of fumaric acid and (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol having at least one or more X-ray diffraction peaks selected from the group consisting of 11.86±0.20 (2θ), 15.26±0.20 (2θ), 16.00±0.20 (2θ), 16.21±0.20 (2θ), 17.52±0.20 (2θ), 21.75±0.20 (2θ), 22.35±0.20 (2θ), 24.57±0.20 (2θ) and 25.21±0.20 (2θ).
11 more elements
Dependencies are inferred from the claim text.