DE60226044T2 - Kristalline formen von fluvastatin-natrium - Google Patents
Kristalline formen von fluvastatin-natrium Download PDFInfo
- Publication number
- DE60226044T2 DE60226044T2 DE60226044T DE60226044T DE60226044T2 DE 60226044 T2 DE60226044 T2 DE 60226044T2 DE 60226044 T DE60226044 T DE 60226044T DE 60226044 T DE60226044 T DE 60226044T DE 60226044 T2 DE60226044 T2 DE 60226044T2
- Authority
- DE
- Germany
- Prior art keywords
- intensity
- crystalline
- ray diffraction
- relative humidity
- crystalline polymorph
- 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.)
- Expired - Lifetime
Links
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 title claims abstract description 40
- 229960000868 fluvastatin sodium Drugs 0.000 title claims abstract description 38
- 238000000034 method Methods 0.000 claims abstract description 12
- 238000002360 preparation method Methods 0.000 claims abstract description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 25
- 238000010586 diagram Methods 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- -1 3- (4-fluorophenyl) -1- (1-methylethyl) -1H-indol-2-yl Chemical group 0.000 claims description 3
- KKEMYLLTGGQWCE-UHFFFAOYSA-M sodium;7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoate;hydrate Chemical compound O.[Na+].C12=CC=CC=C2N(C(C)C)C(C=CC(O)CC(O)CC([O-])=O)=C1C1=CC=C(F)C=C1 KKEMYLLTGGQWCE-UHFFFAOYSA-M 0.000 claims 4
- 239000003937 drug carrier Substances 0.000 claims 1
- NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 claims 1
- 235000011121 sodium hydroxide Nutrition 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000004108 freeze drying Methods 0.000 description 7
- 238000011067 equilibration Methods 0.000 description 5
- ZGGHKIMDNBDHJB-UHFFFAOYSA-M sodium;7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoate Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(C=CC(O)CC(O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-UHFFFAOYSA-M 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 150000004677 hydrates Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- CABVTRNMFUVUDM-VRHQGPGLSA-N (3S)-3-hydroxy-3-methylglutaryl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)C[C@@](O)(CC(O)=O)C)O[C@H]1N1C2=NC=NC(N)=C2N=C1 CABVTRNMFUVUDM-VRHQGPGLSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 238000003109 Karl Fischer titration Methods 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229960003765 fluvastatin Drugs 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000006911 nucleation Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000725 suspension Substances 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/04—Sodium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D209/24—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an alkyl or cycloalkyl radical attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01810756 | 2001-08-03 | ||
| EP01810756 | 2001-08-03 | ||
| PCT/EP2002/008276 WO2003013512A2 (en) | 2001-08-03 | 2002-07-25 | Crystalline forms of fluvastatin sodium |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60226044D1 DE60226044D1 (de) | 2008-05-21 |
| DE60226044T2 true DE60226044T2 (de) | 2009-05-14 |
Family
ID=8184071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60226044T Expired - Lifetime DE60226044T2 (de) | 2001-08-03 | 2002-07-25 | Kristalline formen von fluvastatin-natrium |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6696479B2 (enExample) |
| EP (1) | EP1429757B8 (enExample) |
| JP (2) | JP4681808B2 (enExample) |
| KR (1) | KR100975782B1 (enExample) |
| CN (2) | CN1536999B (enExample) |
| AR (1) | AR036205A1 (enExample) |
| AT (1) | ATE391502T1 (enExample) |
| AU (1) | AU2002333271B2 (enExample) |
| CA (1) | CA2454072A1 (enExample) |
| DE (1) | DE60226044T2 (enExample) |
| ES (1) | ES2304140T3 (enExample) |
| HU (1) | HUP0401141A3 (enExample) |
| IL (2) | IL159861A0 (enExample) |
| PL (1) | PL366905A1 (enExample) |
| RU (1) | RU2334738C2 (enExample) |
| WO (1) | WO2003013512A2 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7087631B2 (en) * | 2002-07-18 | 2006-08-08 | Inotek Pharmaceuticals Corporation | Aryltetrazole compounds, and compositions thereof |
| AU2003250086A1 (en) * | 2002-07-26 | 2004-02-23 | Ciba Specialty Chemicals Holging Inc. | Crystalline polymorphic and amorphous forms of benazepril hydrochloride |
| WO2004096765A2 (en) * | 2003-05-01 | 2004-11-11 | Morepen Laboratories Ltd. | A novel crystalline polymorph of fluvastatin sodium and a process for preparing it |
| US7368468B2 (en) | 2003-06-18 | 2008-05-06 | Teva Pharmaceutical Industries Ltd. | Fluvastatin sodium crystal forms XIV, LXXIII, LXXIX, LXXX and LXXXVII, processes for preparing them, compositions containing them and methods of using them |
| EP1638937B1 (en) * | 2003-06-18 | 2008-12-17 | Teva Pharmaceutical Industries Limited | Fluvastatin sodium crystal form xiv, processes for preparing it, compositions containing it and methods of using it |
| US7368581B2 (en) | 2003-06-18 | 2008-05-06 | Teva Pharmaceutical Industries Ltd. | Process for the preparation of fluvastatin sodium crystal from XIV |
| US7892354B2 (en) * | 2003-10-06 | 2011-02-22 | Solvias Ag | Process for the parallel detection of crystalline forms of molecular solids |
| WO2005037787A1 (en) * | 2003-10-16 | 2005-04-28 | Ciba Specialty Chemicals Holding Inc. | Crystalline form of fluvastatin sodium |
| US20070179166A1 (en) * | 2003-12-24 | 2007-08-02 | Valerie Niddam-Hildesheim | Process for preparation of statins with high syn to anti ratio |
| US7851624B2 (en) * | 2003-12-24 | 2010-12-14 | Teva Pharamaceutical Industries Ltd. | Triol form of rosuvastatin and synthesis of rosuvastatin |
| WO2005080332A1 (en) * | 2004-01-14 | 2005-09-01 | Cadila Healthcare Limited | Novel form of fluvastatin sodium |
| WO2005075467A2 (en) * | 2004-02-06 | 2005-08-18 | Ciba Specialty Chemicals Holding Inc. | Crystalline forms of zolmitriptan |
| US7241800B2 (en) | 2004-03-17 | 2007-07-10 | Mai De Ltd. | Anhydrous amorphous form of fluvastatin sodium |
| WO2006021967A1 (en) * | 2004-08-26 | 2006-03-02 | Biocon Limited | Process for the preparation of fluvastatin sodium form a. |
| WO2006030304A2 (en) * | 2004-09-17 | 2006-03-23 | Ranbaxy Laboratories Limited | Novel forms of fluvastatin sodium, processes for preparation and pharmaceutical compositions thereof |
| WO2006085338A2 (en) * | 2005-02-11 | 2006-08-17 | Jubilant Organosys Limited | Novel polymorphic forms of fluvastatin sodium and process for preparing the same |
| WO2006109147A1 (en) * | 2005-04-12 | 2006-10-19 | Glenmark Pharmaceuticals Limited | Substantially pure amorphous fluvastatin, processes for its preparation and pharmaceutical compositions containing same |
| WO2007039784A2 (en) * | 2005-10-06 | 2007-04-12 | Wockhardt Limited | A novel crystalline polymorph of fluvastatin sodium and process for preparing it |
| WO2007054951A1 (en) * | 2005-11-14 | 2007-05-18 | Hetero Drugs Limited | Process for amorphous esomeprazole |
| TW200804279A (en) * | 2006-02-27 | 2008-01-16 | Teva Pharma | Fluvastatin sodium novel forms and preparation thereof |
| WO2009122425A1 (en) * | 2008-04-04 | 2009-10-08 | Shodhana Laboratories Limited | Novel crystalline form of carvedilol dihydrogen phosphate and related processes |
| CN101684121B (zh) * | 2008-09-22 | 2013-04-03 | 重庆医药工业研究院有限责任公司 | 培美曲塞二酸的新晶型及其制备方法 |
| JP6115288B2 (ja) * | 2012-04-27 | 2017-04-19 | 株式会社島津製作所 | 質量分析におけるピーク検出方法及びそのシステム |
| TW201806928A (zh) * | 2016-07-01 | 2018-03-01 | 第一三共股份有限公司 | 胺基羧酸之酸加成鹽的結晶及其製造方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU204253B (en) * | 1982-11-22 | 1991-12-30 | Sandoz Ag | Process for producing mevalonolactone analogues and derivatives and pharmaceutical compositions containing them |
| PH23486A (en) * | 1982-11-22 | 1989-08-16 | Sanzoz Inc | Indole analogs of mevalonolactone,pharmaceutical compositions containing the same and method of use thereof |
| US4739073A (en) * | 1983-11-04 | 1988-04-19 | Sandoz Pharmaceuticals Corp. | Intermediates in the synthesis of indole analogs of mevalonolactone and derivatives thereof |
| HU9203780D0 (en) * | 1991-12-12 | 1993-03-29 | Sandoz Ag | Stabilized pharmaceutical products of hmg-coa reductase inhibitor and method for producing them |
| HRP960313B1 (en) | 1995-07-17 | 2002-08-31 | Warner Lambert Co | Form iii crystalline (r- (r*, r*)-2- (4-fluorophenyl) -beta-delta-hydroxy-5-(1-methylethyl) -3-phenyl-4- ((phenylamino) carbonyl -1h-pyrrole-1-heptanoic acid calcium salt (2:1) |
| PT907639E (pt) * | 1996-06-24 | 2003-06-30 | Novartis Ag | Compostos polimorficos |
| ES2247193T3 (es) * | 2000-10-31 | 2006-03-01 | Ciba Specialty Chemicals Holding Inc. | Formas cristalinas del fluvastatin sodico. |
-
2002
- 2002-07-25 CA CA002454072A patent/CA2454072A1/en not_active Abandoned
- 2002-07-25 KR KR1020047001615A patent/KR100975782B1/ko not_active Expired - Fee Related
- 2002-07-25 EP EP02794517A patent/EP1429757B8/en not_active Expired - Lifetime
- 2002-07-25 WO PCT/EP2002/008276 patent/WO2003013512A2/en not_active Ceased
- 2002-07-25 ES ES02794517T patent/ES2304140T3/es not_active Expired - Lifetime
- 2002-07-25 AT AT02794517T patent/ATE391502T1/de not_active IP Right Cessation
- 2002-07-25 HU HU0401141A patent/HUP0401141A3/hu unknown
- 2002-07-25 RU RU2004106528/04A patent/RU2334738C2/ru not_active IP Right Cessation
- 2002-07-25 DE DE60226044T patent/DE60226044T2/de not_active Expired - Lifetime
- 2002-07-25 CN CN028151321A patent/CN1536999B/zh not_active Expired - Fee Related
- 2002-07-25 IL IL15986102A patent/IL159861A0/xx active IP Right Grant
- 2002-07-25 PL PL02366905A patent/PL366905A1/xx not_active Application Discontinuation
- 2002-07-25 JP JP2003518521A patent/JP4681808B2/ja not_active Expired - Fee Related
- 2002-07-25 AU AU2002333271A patent/AU2002333271B2/en not_active Ceased
- 2002-07-25 CN CN2011103995817A patent/CN102516150A/zh active Pending
- 2002-07-30 US US10/208,687 patent/US6696479B2/en not_active Expired - Lifetime
- 2002-08-01 AR ARP020102927A patent/AR036205A1/es unknown
-
2004
- 2004-01-14 IL IL159861A patent/IL159861A/en not_active IP Right Cessation
-
2010
- 2010-07-23 JP JP2010165635A patent/JP2010265308A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002333271B2 (en) | 2007-08-09 |
| ATE391502T1 (de) | 2008-04-15 |
| DE60226044D1 (de) | 2008-05-21 |
| US6696479B2 (en) | 2004-02-24 |
| CN1536999B (zh) | 2012-08-08 |
| CA2454072A1 (en) | 2003-02-20 |
| US20030032666A1 (en) | 2003-02-13 |
| ES2304140T3 (es) | 2008-09-16 |
| WO2003013512A2 (en) | 2003-02-20 |
| HUP0401141A2 (hu) | 2004-09-28 |
| KR20040022226A (ko) | 2004-03-11 |
| IL159861A0 (en) | 2004-06-20 |
| CN102516150A (zh) | 2012-06-27 |
| JP2005501838A (ja) | 2005-01-20 |
| EP1429757B1 (en) | 2008-04-09 |
| IL159861A (en) | 2009-02-11 |
| HUP0401141A3 (en) | 2011-07-28 |
| KR100975782B1 (ko) | 2010-08-17 |
| EP1429757A2 (en) | 2004-06-23 |
| EP1429757B8 (en) | 2008-07-16 |
| WO2003013512A3 (en) | 2003-11-20 |
| AR036205A1 (es) | 2004-08-18 |
| JP4681808B2 (ja) | 2011-05-11 |
| JP2010265308A (ja) | 2010-11-25 |
| PL366905A1 (en) | 2005-02-07 |
| RU2334738C2 (ru) | 2008-09-27 |
| RU2004106528A (ru) | 2005-07-27 |
| CN1536999A (zh) | 2004-10-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8327 | Change in the person/name/address of the patent owner |
Owner name: CIBA HOLDING INC., BASEL, CH |
|
| 8328 | Change in the person/name/address of the agent |
Representative=s name: TER MEER STEINMEISTER & PARTNER GBR PATENTANWAELTE |
|
| 8364 | No opposition during term of opposition |