CA2614979A1 - Piretanide polymorph, process for its preparation and its use - Google Patents
Piretanide polymorph, process for its preparation and its use Download PDFInfo
- Publication number
- CA2614979A1 CA2614979A1 CA002614979A CA2614979A CA2614979A1 CA 2614979 A1 CA2614979 A1 CA 2614979A1 CA 002614979 A CA002614979 A CA 002614979A CA 2614979 A CA2614979 A CA 2614979A CA 2614979 A1 CA2614979 A1 CA 2614979A1
- Authority
- CA
- Canada
- Prior art keywords
- piretanide
- peak
- compound
- around
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- UJEWTUDSLQGTOA-UHFFFAOYSA-N Piretanide Chemical compound C=1C=CC=CC=1OC=1C(S(=O)(=O)N)=CC(C(O)=O)=CC=1N1CCCC1 UJEWTUDSLQGTOA-UHFFFAOYSA-N 0.000 title claims abstract 8
- 229960001085 piretanide Drugs 0.000 title claims abstract 8
- 238000002360 preparation method Methods 0.000 title claims 3
- 238000000034 method Methods 0.000 title claims 2
- 230000009102 absorption Effects 0.000 claims abstract 3
- 238000010521 absorption reaction Methods 0.000 claims abstract 3
- 238000000862 absorption spectrum Methods 0.000 claims abstract 3
- 239000002253 acid Substances 0.000 claims abstract 3
- 238000004458 analytical method Methods 0.000 claims abstract 3
- 239000007864 aqueous solution Substances 0.000 claims abstract 3
- 238000002844 melting Methods 0.000 claims abstract 3
- 230000008018 melting Effects 0.000 claims abstract 3
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract 3
- 239000002244 precipitate Substances 0.000 claims abstract 3
- 239000000243 solution Substances 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims 4
- 206010030113 Oedema Diseases 0.000 claims 2
- 239000000654 additive Substances 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 1
- 238000002347 injection Methods 0.000 abstract 2
- 239000007924 injection Substances 0.000 abstract 2
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Amorphous piretanide having the following characteristics: a) exothermic peaks at about 136°C and about 209°C, b) an endothermic peak at about 207°C, and c) a melting peak at about 225°C in differential thermal curves; d) a halopattern without diffraction peak (20) in X-ray powder diffraction analysis; and e) characteristic absorptions at around 1700 cm-1 and 3200-3500 cm-1 in infra-red absorption spectrum, and having a superior solubility around neutrality and a high bioavailability effective in the manner of oral or injection administration, which is prepared by dissolving piretanide in an aqueous solution of a base, adjusting a pH value of the solution by an acid to a pH range from not less than 3.87 to not more than 4.37 and recovering the precipitate thus separated, and piretanide polymorph having the following characteristics: a) an endothermic peak at about 132°C, b) an exothermic peak at about 143°C, and c) a melting peak at about 224°C in differential thermal curves; d) diffraction peaks (2.theta.) at 10.5, 12.2, 15.6, 19.1, 19.9, 22.0, 22.8, 25.6 and 30.6 in X-ray powder diffraction analysis; and e) characteristic absorption at around 1700 cm-1 and 3200-3500 cm-1 in infra-red absorption spectrum, and having a superior solubility around neutrality and a high bioavailability effective in the manner of oral or injection administration, which is prepared by dissolving piretanide in an aqueous solution of a base, adjusting a pH value of the solution to a pH range of less than 3.50 by an acid and recovering the precipitate thus separated.
Claims (6)
1. A piretanide polymorph having the following characteristics:
(a) an endothermic peak at about 132°C, (b) an exothermic peak at about 143°C, and (c) a melting peak at about 224°C, in differential thermal curves (d) diffraction peaks (2.theta.) at 10.5, 12.2, 15.6, 19.1, 19.9, 22.0, 22.8, 25.6 and 30.6 in X-ray powder diffraction analysis; and (e) characteristic absorptions at around 1700 cm-1 and 3200 - 3500 cm-1 in an infra-red absorption spectrum.
(a) an endothermic peak at about 132°C, (b) an exothermic peak at about 143°C, and (c) a melting peak at about 224°C, in differential thermal curves (d) diffraction peaks (2.theta.) at 10.5, 12.2, 15.6, 19.1, 19.9, 22.0, 22.8, 25.6 and 30.6 in X-ray powder diffraction analysis; and (e) characteristic absorptions at around 1700 cm-1 and 3200 - 3500 cm-1 in an infra-red absorption spectrum.
2. A process for preparing a piretanide polymorph as claimed in claim 1, which comprises dissolving piretanide in an aqueous solution of a base, adjusting a pH value of the solution by an acid to a pH range of less than 3.50 and recovering the precipitate thus separated.
3. A compound as claimed in claim 1 for use as a medicament for the treatment and prevention of edema.
4. A pharmaceutical preparation containing a compound as claimed in claim 1, and a physiologically acceptable excipient, and, optionally other additives or auxiliaries.
5. A process for the production of a preparations as claimed in claim 4, which comprises bringing a compound as claimed in claim 1 into a suitable administration form together with a physiologically acceptable excipient and, optionally, other additives or auxiliaries.
6. The use of a compound as claimed in claim 1 for the preparation of a pharmaceutical preparation for the treatment and prevention of edema.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP03321595A JP3532987B2 (en) | 1995-02-22 | 1995-02-22 | Novel amorphous piretanide and method for producing the same |
| JP7/33215 | 1995-02-22 | ||
| JP03321695A JP3532988B2 (en) | 1995-02-22 | 1995-02-22 | Novel crystalline polymorph of piretanide and method for producing the same |
| JP7/33216 | 1995-02-22 | ||
| CA002213693A CA2213693C (en) | 1995-02-22 | 1996-02-12 | Amorphous piretanide, piretanide polymorphs, process for their preparation and their use |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002213693A Division CA2213693C (en) | 1995-02-22 | 1996-02-12 | Amorphous piretanide, piretanide polymorphs, process for their preparation and their use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2614979A1 true CA2614979A1 (en) | 1996-08-29 |
| CA2614979C CA2614979C (en) | 2011-03-22 |
Family
ID=39264350
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2614979A Expired - Lifetime CA2614979C (en) | 1995-02-22 | 1996-02-12 | Piretanide polymorph, process for its preparation and its use |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2614979C (en) |
-
1996
- 1996-02-12 CA CA2614979A patent/CA2614979C/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2614979C (en) | 2011-03-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKEX | Expiry |
Effective date: 20160212 |