SI21702A - Preparation of amorphous form of tamsulosin - Google Patents
Preparation of amorphous form of tamsulosin Download PDFInfo
- Publication number
- SI21702A SI21702A SI200400032A SI200400032A SI21702A SI 21702 A SI21702 A SI 21702A SI 200400032 A SI200400032 A SI 200400032A SI 200400032 A SI200400032 A SI 200400032A SI 21702 A SI21702 A SI 21702A
- Authority
- SI
- Slovenia
- Prior art keywords
- tamsulosin hydrochloride
- tamsulosin
- amorphous form
- hydrochloride
- preparation
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- DRHKJLXJIQTDTD-OAHLLOKOSA-N Tamsulosine Chemical compound CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 DRHKJLXJIQTDTD-OAHLLOKOSA-N 0.000 title claims description 14
- 229960002613 tamsulosin Drugs 0.000 title description 13
- ZZIZZTHXZRDOFM-UHFFFAOYSA-N 2-(2-ethoxyphenoxy)ethyl-[1-(4-methoxy-3-sulfamoylphenyl)propan-2-yl]azanium;chloride Chemical compound Cl.CCOC1=CC=CC=C1OCCNC(C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 ZZIZZTHXZRDOFM-UHFFFAOYSA-N 0.000 claims abstract description 37
- 229960003198 tamsulosin hydrochloride Drugs 0.000 claims abstract description 36
- 238000000034 method Methods 0.000 claims abstract description 14
- 238000004108 freeze drying Methods 0.000 claims abstract description 6
- 239000013543 active substance Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 2
- 208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 238000001694 spray drying Methods 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000004566 IR spectroscopy Methods 0.000 description 3
- 238000007707 calorimetry Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000000634 powder X-ray diffraction Methods 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000011197 physicochemical method Methods 0.000 description 2
- ODLMAHJVESYWTB-UHFFFAOYSA-N propylbenzene Chemical compound CCCC1=CC=CC=C1 ODLMAHJVESYWTB-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- ZZIZZTHXZRDOFM-XFULWGLBSA-N tamsulosin hydrochloride Chemical compound [H+].[Cl-].CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 ZZIZZTHXZRDOFM-XFULWGLBSA-N 0.000 description 2
- 238000001757 thermogravimetry curve Methods 0.000 description 2
- IOYHGBZPUZBUTJ-UHFFFAOYSA-N 1-(2-bromoethoxy)-2-ethoxybenzene Chemical compound CCOC1=CC=CC=C1OCCBr IOYHGBZPUZBUTJ-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- DRHKJLXJIQTDTD-UHFFFAOYSA-N 5-(2-{[2-(2-ethoxyphenoxy)ethyl]amino}propyl)-2-methoxybenzenesulfonamide Chemical compound CCOC1=CC=CC=C1OCCNC(C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 DRHKJLXJIQTDTD-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI200400032A SI21702A (en) | 2004-01-29 | 2004-01-29 | Preparation of amorphous form of tamsulosin |
| PCT/EP2005/000875 WO2005075416A1 (en) | 2004-01-29 | 2005-01-28 | Amorphous tamsulosin hydrochloride |
| SI200530764T SI1713769T1 (sl) | 2004-01-29 | 2005-01-28 | Priprava amorfne oblike tamsulozina |
| US10/587,376 US20070161709A1 (en) | 2004-01-29 | 2005-01-28 | Amorphous tamsulosin hydrochloride |
| EP05715224A EP1713769B1 (de) | 2004-01-29 | 2005-01-28 | Amorphes tamsulosin-hydrochlorid |
| AT05715224T ATE434604T1 (de) | 2004-01-29 | 2005-01-28 | Amorphes tamsulosin-hydrochlorid |
| DE602005015083T DE602005015083D1 (de) | 2004-01-29 | 2005-01-28 | Amorphes tamsulosin-hydrochlorid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI200400032A SI21702A (en) | 2004-01-29 | 2004-01-29 | Preparation of amorphous form of tamsulosin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SI21702A true SI21702A (en) | 2005-08-31 |
Family
ID=34836935
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI200400032A SI21702A (en) | 2004-01-29 | 2004-01-29 | Preparation of amorphous form of tamsulosin |
| SI200530764T SI1713769T1 (sl) | 2004-01-29 | 2005-01-28 | Priprava amorfne oblike tamsulozina |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI200530764T SI1713769T1 (sl) | 2004-01-29 | 2005-01-28 | Priprava amorfne oblike tamsulozina |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20070161709A1 (de) |
| EP (1) | EP1713769B1 (de) |
| AT (1) | ATE434604T1 (de) |
| DE (1) | DE602005015083D1 (de) |
| SI (2) | SI21702A (de) |
| WO (1) | WO2005075416A1 (de) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH066565B2 (ja) * | 1986-07-21 | 1994-01-26 | 山之内製薬株式会社 | 光学活性なベンゼンスルホンアミド誘導体の製造法 |
| US6395300B1 (en) * | 1999-05-27 | 2002-05-28 | Acusphere, Inc. | Porous drug matrices and methods of manufacture thereof |
| US6835853B2 (en) * | 2001-10-31 | 2004-12-28 | Synthon Bv | Process for resolution of tamsulosin and compounds, compositions, and processes associated therewith |
| PT1443917E (pt) * | 2001-11-07 | 2006-06-30 | Synthon Bv | Comprimidos de tamsulosina |
-
2004
- 2004-01-29 SI SI200400032A patent/SI21702A/sl not_active IP Right Cessation
-
2005
- 2005-01-28 SI SI200530764T patent/SI1713769T1/sl unknown
- 2005-01-28 US US10/587,376 patent/US20070161709A1/en not_active Abandoned
- 2005-01-28 AT AT05715224T patent/ATE434604T1/de not_active IP Right Cessation
- 2005-01-28 WO PCT/EP2005/000875 patent/WO2005075416A1/en not_active Ceased
- 2005-01-28 EP EP05715224A patent/EP1713769B1/de not_active Expired - Lifetime
- 2005-01-28 DE DE602005015083T patent/DE602005015083D1/de not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US20070161709A1 (en) | 2007-07-12 |
| EP1713769B1 (de) | 2009-06-24 |
| ATE434604T1 (de) | 2009-07-15 |
| EP1713769A1 (de) | 2006-10-25 |
| SI1713769T1 (sl) | 2009-10-31 |
| DE602005015083D1 (de) | 2009-08-06 |
| WO2005075416A1 (en) | 2005-08-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OO00 | Grant of patent |
Effective date: 20040629 |
|
| KO00 | Lapse of patent |
Effective date: 20130903 |