SK50782006A3 - Amorfné formy risedronátu monosodného - Google Patents
Amorfné formy risedronátu monosodného Download PDFInfo
- Publication number
- SK50782006A3 SK50782006A3 SK5078-2006A SK50782006A SK50782006A3 SK 50782006 A3 SK50782006 A3 SK 50782006A3 SK 50782006 A SK50782006 A SK 50782006A SK 50782006 A3 SK50782006 A3 SK 50782006A3
- Authority
- SK
- Slovakia
- Prior art keywords
- risedronate
- substance
- temperature
- formula
- heated
- Prior art date
Links
- DRFDPXKCEWYIAW-UHFFFAOYSA-M Risedronate sodium Chemical compound [Na+].OP(=O)(O)C(P(O)([O-])=O)(O)CC1=CC=CN=C1 DRFDPXKCEWYIAW-UHFFFAOYSA-M 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 22
- 239000002253 acid Substances 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 13
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims abstract description 12
- IIDJRNMFWXDHID-UHFFFAOYSA-N Risedronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CC1=CC=CN=C1 IIDJRNMFWXDHID-UHFFFAOYSA-N 0.000 claims description 87
- 229960000759 risedronic acid Drugs 0.000 claims description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 46
- 229940089617 risedronate Drugs 0.000 claims description 40
- 239000000126 substance Substances 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 9
- 238000001875 carbon-13 cross-polarisation magic angle spinning nuclear magnetic resonance spectrum Methods 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000002552 dosage form Substances 0.000 claims description 7
- 150000004686 pentahydrates Chemical class 0.000 claims description 7
- 239000007921 spray Substances 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 6
- 238000002329 infrared spectrum Methods 0.000 claims description 6
- 238000001237 Raman spectrum Methods 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 238000002441 X-ray diffraction Methods 0.000 claims description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 claims description 2
- 229930195725 Mannitol Natural products 0.000 claims description 2
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 2
- 239000000594 mannitol Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 2
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 2
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims 1
- 239000004744 fabric Substances 0.000 claims 1
- 238000005507 spraying Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000004090 dissolution Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- -1 alkaline earth metal salts Chemical class 0.000 description 7
- 210000002784 stomach Anatomy 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 239000013543 active substance Substances 0.000 description 5
- 150000004682 monohydrates Chemical class 0.000 description 5
- 238000000722 phosphorus-31 cross-polarisation magic angle spinning nuclear magnetic resonance spectrum Methods 0.000 description 5
- 238000002411 thermogravimetry Methods 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 4
- 150000004677 hydrates Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 210000000813 small intestine Anatomy 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000001160 cross-polarisation magic angle spinning nuclear magnetic resonance spectrum Methods 0.000 description 3
- 238000000634 powder X-ray diffraction Methods 0.000 description 3
- 229940122361 Bisphosphonate Drugs 0.000 description 2
- 150000004663 bisphosphonates Chemical group 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- WGNUNYPERJMVRM-UHFFFAOYSA-N 3-pyridylacetic acid Chemical compound OC(=O)CC1=CC=CN=C1 WGNUNYPERJMVRM-UHFFFAOYSA-N 0.000 description 1
- OGSPWJRAVKPPFI-UHFFFAOYSA-N Alendronic Acid Chemical compound NCCCC(O)(P(O)(O)=O)P(O)(O)=O OGSPWJRAVKPPFI-UHFFFAOYSA-N 0.000 description 1
- 208000020084 Bone disease Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229940037127 actonel Drugs 0.000 description 1
- 229940062527 alendronate Drugs 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000003913 calcium metabolism Effects 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 229950007593 homonicotinic acid Drugs 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Physical Education & Sports Medicine (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CZ20040292A CZ298383B6 (cs) | 2004-02-26 | 2004-02-26 | Amorfní forma risedronátu monosodného |
| CZ20040798A CZ298328B6 (cs) | 2004-07-08 | 2004-07-08 | Semikrystalická forma risedronátu monosodného, zpusob jeho prípravy a léková forma ho obsahující |
| CZ20040880A CZ298491B6 (cs) | 2004-08-12 | 2004-08-12 | Zpusob prípravy amorfní formy risedronátu monosodného |
| PCT/CZ2005/000024 WO2005082915A1 (en) | 2004-02-26 | 2005-02-28 | Amorphous forms of risedronate monosodium |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK50782006A3 true SK50782006A3 (sk) | 2007-03-01 |
Family
ID=34915827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK5078-2006A SK50782006A3 (sk) | 2004-02-26 | 2005-02-28 | Amorfné formy risedronátu monosodného |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7618953B2 (pl) |
| EP (1) | EP1723157B2 (pl) |
| DE (1) | DE602005003557D1 (pl) |
| EA (1) | EA009737B1 (pl) |
| PL (2) | PL1723157T5 (pl) |
| SK (1) | SK50782006A3 (pl) |
| UA (1) | UA83900C2 (pl) |
| WO (1) | WO2005082915A1 (pl) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE602005001873T2 (de) | 2004-03-03 | 2008-04-24 | Chemi S.P.A., Cinisello Balsamo | Amorphe 3-Pyridyl-1-Hydroxyethyliden-1,1-Bisphosphonsäure Mononatriumsalz und Verfahren zu deren Herstellung |
| KR20070106680A (ko) * | 2004-09-30 | 2007-11-05 | 닥터 레디스 레보러터리즈 리미티드 | 비정질 아토르바스타틴 칼슘 |
| EP1891081B1 (en) * | 2005-06-13 | 2014-08-20 | Jubilant Organosys Limited | Process for producing bisphosphonic acids and forms thereof |
| GB0519891D0 (en) * | 2005-09-30 | 2005-11-09 | Pliva Hrvatska D O O | Pharmaceutically acceptable salts and hydrates |
| JP5354858B2 (ja) * | 2006-05-09 | 2013-11-27 | 株式会社Ａｄｅｋａ | スルホンアミド化合物の金属塩を含有するポリエステル樹脂組成物 |
| WO2007132478A2 (en) | 2006-05-11 | 2007-11-22 | Ind-Swift Laboratories Limited | Process for the preparation of pure risedronic acid or salts |
| KR100775440B1 (ko) * | 2006-12-20 | 2007-11-12 | 동우신테크 주식회사 | 리세드로네이트 나트륨 헤미펜타히드레이트의 제조방법 |
| DE102007030370A1 (de) | 2007-06-29 | 2009-01-02 | Ratiopharm Gmbh | Essigsäure-Solvate von Risedronat, Polymorph hiervon, deren Herstellung und Verwendung sowie pharmazeutische Zusammensetzung, enthaltend diese |
| KR101010062B1 (ko) | 2008-04-11 | 2011-01-21 | 주식회사 대희화학 | 증발 결정화를 이용한 결정상 리세드로네이트 모노소듐모노하이드레이트의 제조방법 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1378234A1 (en) † | 1996-05-17 | 2004-01-07 | MERCK & CO. INC. | Effervescent bisphosphonate formulation |
| KR19990001564A (ko) † | 1997-06-16 | 1999-01-15 | 유충식 | 용해도를 개선한 아졸계 항진균제 및 이를 함유하는 제제 |
| PL351674A1 (en) † | 1999-05-21 | 2003-05-19 | Novartis Ag | Use of bisphosphonic acids for treating angiogenesis |
| US6410520B2 (en) | 2000-02-01 | 2002-06-25 | The Procter & Gamble Company | Selective crystallization of 3-pyridyl-1-hydroxyethylidene-1, 1-bisphosphonic acid sodium as the hemipentahydrate or monohydrate |
| GB2383042A (en) † | 2001-10-18 | 2003-06-18 | Cipla Ltd | Amorphous alendronate sodium |
| US20030195170A1 (en) † | 2002-04-11 | 2003-10-16 | Judith Aronhime | Novel polymorphs and pseudopolymorphs of risedronate sodium |
| CZ293349B6 (cs) | 2002-10-25 | 2004-04-14 | Léčiva, A.S. | Nová krystalická forma sodné soli kyseliny 3-pyridyl-1-hydroxyethyliden-1,1-bisfosfonové |
| CZ298639B6 (cs) † | 2004-02-05 | 2007-12-05 | Zentiva, A. S. | Krystalická forma risedronátu monosodného |
| DE602005001873T2 (de) † | 2004-03-03 | 2008-04-24 | Chemi S.P.A., Cinisello Balsamo | Amorphe 3-Pyridyl-1-Hydroxyethyliden-1,1-Bisphosphonsäure Mononatriumsalz und Verfahren zu deren Herstellung |
| EP1891081B1 (en) † | 2005-06-13 | 2014-08-20 | Jubilant Organosys Limited | Process for producing bisphosphonic acids and forms thereof |
-
2005
- 2005-02-28 DE DE602005003557T patent/DE602005003557D1/de not_active Expired - Lifetime
- 2005-02-28 EA EA200601438A patent/EA009737B1/ru not_active IP Right Cessation
- 2005-02-28 PL PL05706666T patent/PL1723157T5/pl unknown
- 2005-02-28 PL PL380663A patent/PL213481B1/pl unknown
- 2005-02-28 SK SK5078-2006A patent/SK50782006A3/sk not_active Application Discontinuation
- 2005-02-28 US US10/590,694 patent/US7618953B2/en not_active Expired - Lifetime
- 2005-02-28 EP EP05706666.4A patent/EP1723157B2/en not_active Expired - Lifetime
- 2005-02-28 WO PCT/CZ2005/000024 patent/WO2005082915A1/en not_active Ceased
- 2005-02-28 UA UAA200610284A patent/UA83900C2/ru unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1723157A1 (en) | 2006-11-22 |
| PL1723157T3 (pl) | 2008-04-30 |
| EA200601438A1 (ru) | 2006-12-29 |
| DE602005003557D1 (de) | 2008-01-10 |
| EP1723157B1 (en) | 2007-11-28 |
| EP1723157B2 (en) | 2017-02-08 |
| UA83900C2 (en) | 2008-08-26 |
| PL213481B1 (pl) | 2013-03-29 |
| US7618953B2 (en) | 2009-11-17 |
| WO2005082915A1 (en) | 2005-09-09 |
| PL1723157T5 (pl) | 2018-01-31 |
| US20070142332A1 (en) | 2007-06-21 |
| EA009737B1 (ru) | 2008-02-28 |
| PL380663A1 (pl) | 2007-02-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TA4A | Addition of inventor(s) |
Effective date: 20101123 |
|
| TC4A | Change of owner's name |
Owner name: ZENTIVA, K.S., PRAHA, DOLNI MECHOLUPY, CZ Effective date: 20120524 |
|
| FC9A | Refused patent application |