WO2000042024A1 - Crystalline bis[(e)-7- [ 4-(4- fluorophenyl)- 6-isopropyl-2- [methyl (methylsulfonyl) amino] pyrimidin -5-yl] (3r,5s)-3, 5-dihydroxyhept -6-enoic acid]calcium salt - Google Patents
Crystalline bis[(e)-7- [ 4-(4- fluorophenyl)- 6-isopropyl-2- [methyl (methylsulfonyl) amino] pyrimidin -5-yl] (3r,5s)-3, 5-dihydroxyhept -6-enoic acid]calcium salt Download PDFInfo
- Publication number
- WO2000042024A1 WO2000042024A1 PCT/GB1999/004439 GB9904439W WO0042024A1 WO 2000042024 A1 WO2000042024 A1 WO 2000042024A1 GB 9904439 W GB9904439 W GB 9904439W WO 0042024 A1 WO0042024 A1 WO 0042024A1
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- Prior art keywords
- crystalline form
- methyl
- crystalline
- manufacture
- dihydroxyhept
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Definitions
- the present invention relates to a novel crystalline chemical compound and more particularly to a novel crystalline form of bis[(E)-7-[4-(4-fluorophenyl)-6-isopropyl-2- [methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxyhept-6-enoic acid] calcium salt, hereinafter referred to as "the Agent”, and illustrated in Formula I hereinafter, which compound is an inhibitor of the enzyme 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG CoA reductase) and is useful as a pharmaceutical agent, for example in the treatment of hyperlipidemia, hypercholesterolemia and atherosclerosis, as well as other diseases or conditions in which HMG CoA reductase is implicated.
- the invention also relates to processes for the manufacture of the crystalline form, pharmaceutical compositions comprising the crystalline form and the use of the crystalline form in medical treatment.
- EPA 521471 discloses an amorphous (powder) form of the Agent, prepared by dissolving the corresponding sodium salt in water, adding calcium chloride and collecting the resultant precipitate by filtration.
- An amorphous form of a compound intended for pharmaceutical use may give rise to manufacturing problems and there is a need to identify crystalline forms of such compounds which have different physical characteristics compared to the amorphous form which may assist in the manufacture of the compound, or formulation of the compound, to the purity levels and uniformity required for regulatory approval. Crystalline forms of such compounds may also possess improved pharmacological characteristics, for example, improved bioavailability.
- the Agent can be prepared in a crystalline form.
- the X-ray powder diffraction spectra was determined by mounting a sample of the crystalline form on Siemans single silicon crystal (SSC) wafer mounts and spreading out the sample into a thin layer with the aid of a microscope slide. The sample was spun at 30 revolutions per minute (to improve counting statistics) and irradiated with X-rays generated by a copper long-fine focus tube operated at 40kV and 40mA with a wavelength of 1.5406 angstroms. The collimated x-ray source was passed through an automatic variable divergence slit set at N20 (20mm path length) and the reflected radiation directed through a 2mm antiscatter slit and a 0.2mm detector slit.
- SSC Siemans single silicon crystal
- the sample was exposed for 4 seconds per 0.02 degree 2-theta increment (continuous scan mode) over the range 2 degrees to 40 degrees 2- theta in theta-theta mode.
- the running time was 2 hours 6 minutes and 40 seconds.
- the instrument was equipped with a scintillation counter as detector. Control and data capture was by means of a DECpc LPv 433sx personal computer running with Diffrac AT (Socabim) software.
- the X-ray powder diffraction spectra of a typical sample of Form A is shown in Figure 1 hereinafter. It will be understood that the 2-theta values of the X-ray powder diffraction pattern may vary slightly from one machine to another or from one sample of Form A to another, and so the values quoted are not to be construed as absolute.
- Form A is obtained in a hydrated form with, for example, a water content of about 7% w/w.
- a further aspect of the present invention comprises a process for the preparation of Form A wherein Form A is caused to crystallise from a mixture of the Agent, water and one or more organic solvents.
- the optimum ratio of organic solvents and water in the mixture to obtain Form A is dependent on the characteristics of the organic solvents used and the process conditions employed. The precise conditions may be empirically determined.
- Form A may be obtained by suspending the amorphous form of the Agent in water containing a co-solvent, such as acetonitrile, acetone or a mixture of methanol and methyl tert-butyl ether (MTBE), warming the mixture to obtain complete solution and then allowing the solution to cool, followed by isolation of Form A, such as by filtration.
- a co-solvent such as acetonitrile, acetone or a mixture of methanol and methyl tert-butyl ether (MTBE)
- Suitable mixtures of water and co-solvent include, for example, 1 : 1 water/acetonitrile, 1 : 1 water/acetone and 1:1:1 water/methanol/MTBE, the ratios given being by volume.
- the amorphous form of the Agent to be used as starting material for the manufacture of Form A may be obtained, for example, as described in EPA 521471.
- the utility of the compound of the invention may be demonstrated by standard tests and clinical studies, including those described in EPA 521471.
- a further feature of the invention is a method of treating a disease condition wherein inhibition of HMG CoA reductase is beneficial which comprises administering to a warm-blooded mammal an effective amount of the Agent.
- the invention also relates to the use of Form A in the manufacture of a medicament for use in a disease condition.
- the compound of the invention may be administered to a warm-blooded animal, particularly a human, in need thereof for treatment of a disease in which HMG CoA reductase is implicated, in the form of a conventional pharmaceutical composition. Therefore in another aspect of the invention, there is provided a pharmaceutical composition comprising Form A in admixture with a pharmaceutically acceptable carrier.
- compositions may be administered in standard manner for the disease condition that it is desired to treat, for example by oral, topical, parenteral, buccal, nasal, vaginal or rectal administration or by inhalation.
- the Agent may be formulated by means known in the art into the form of, for example, tablets, capsules, aqueous or oily solutions, suspensions, emulsions, creams, ointments, gels, nasal sprays, suppositories, finely divided powders or aerosols for inhalation, and for parenteral use (including intravenous, intramuscular or infusion) sterile aqueous or oily solution or suspensions or sterile emulsions.
- a preferred route of administration is oral.
- the Agent will be administered to humans at a daily dose in, for example, the ranges set out in EPA 521471.
- the daily doses may be given in divided doses as necessary, the precise amount of the Agent received and the route of administration depending on the weight, age and sex of the patient being treated and on the particular disease condition being treated according to principles known in the art.
- a process for the manufacture of a pharmaceutical composition containing Form A as active ingredient which comprises admixing Form A together with a pharmaceutically acceptable carrier.
- Amorphous form of the Agent (465 mg) was added to a mixture of water (5 ml) and acetonitrile (5 ml) at 15°C. The mixture was warmed to 40°C to obtain complete solution. The mixture was then cooled slowly to ambient temperature and stirred for 16 hours. The crystalline product was separated by filtration at ambient temperature and dried at 50° under vacuum to give Form A (337 mg) as white crystals.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Description
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Priority Applications (17)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AT99962471T ATE282027T1 (en) | 1999-01-09 | 1999-12-23 | CRYSTALLINE BIS((E)-7-(4-(4-FLUOROPHENYL)-6- ISOPROPYL-2- |
SI9930731T SI1144389T1 (en) | 1999-01-09 | 1999-12-23 | Crystalline bis((e)-7-(4-(4-fluorophenyl)-6-isopropyl-2-(methyl(methylsulfonyl)amino)pyrimidin-5-yl)(3r,5s)-3,5-dihydroxyhept-6-enoicacid)calcium salt |
US09/869,462 US6589959B1 (en) | 1999-01-09 | 1999-12-23 | Crystalline bis[(e)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxyhept-6-enoic acid]calcium salt |
NZ512560A NZ512560A (en) | 1999-01-09 | 1999-12-23 | HMG CoA Reductase Inhibitor Crystalline bis[(E)-7- [ 4-(4- fluorophenyl)- 6-isopropyl-2-[methyl (methylsulfonyl) amino] pyrimidin -5-YL] (3R,5S)-3, 5-dihydroxyhept -6-enoic acid]calcium salt |
EP99962471A EP1144389B1 (en) | 1999-01-09 | 1999-12-23 | Crystalline bis[(e)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3r,5s)-3,5-dihydroxyhept-6-enoicacid]calcium salt |
DE69921855T DE69921855T2 (en) | 1999-01-09 | 1999-12-23 | CRYSTALLINE TO [(E) -7- [4- (4-FLUORO-PHENYL) -6-ISOPROPYL-2- [METHYL (METHYLSULFONYL) AMINO] PYRIMIDIN-5-YL] (3R, 5S) -3,5-DIHYDROXY-HEPT-6 -ENOICACID] CALCIUM SALT |
CA002356212A CA2356212C (en) | 1999-01-09 | 1999-12-23 | Crystalline bis[(e)-7- [ 4-(4- fluorophenyl)- 6-isopropyl-2- [methyl (methylsulfonyl) amino] pyrimidin -5-yl] (3r,5s)-3, 5-dihydroxyhept -6-enoic acid]calcium salt |
EEP200100359A EE05033B1 (en) | 1999-01-09 | 1999-12-23 | Crystalline bis [(E) -7- [4- (4-fluorophenyl) -6-isopropyl-2- [methyl (methylsulfonyl) amino] pyrimidine 5- 1] (3R, 5S) -3,5-Dihroxo-hept-6-enol acid] Calcium salt |
BR9916786-7A BR9916786A (en) | 1999-01-09 | 1999-12-23 | Crystalline form of a compound, pharmaceutical composition, processes for the manufacture of a crystalline form or a hydrated form and a pharmaceutical composition, use of a crystalline form, and method of treating an unhealthy condition |
HU0104828A HU228116B1 (en) | 1999-01-09 | 1999-12-23 | Crystalline bis[(e)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl-(methylsulfonyl)amino]pyrimidin-5-yl](3r,5s)-1,5-dihydroxyhept-6-enoic acid]calcium salt, pharmaceutical composition containing it and process for its preparation |
JP2000593592A JP4996786B2 (en) | 1999-01-09 | 1999-12-23 | The crystalline compound bis [(E) -7- [4- (4-fluorophenyl) -6-isopropyl-2- [methyl (methylsulfonyl) amino] pyrimidin-5-yl] (3R, 5S) -3, 5-Dihydroxy-6-heptenoic acid] calcium salt |
SK963-2001A SK285807B6 (en) | 1999-01-09 | 1999-12-23 | Crystalline form of bis[(E)-7-[4-(4-fluorophenyl)-6-isopropyl-2- [methyl(methylsulfonyl)amino]pyrimidin-5-yl]-(3R,5S)-3,5- dihydroxyhept-6-enoic acid]calcium salt, pharmaceutical composition containing it, process for its preparation and use this crystalline form |
AU18826/00A AU762909B2 (en) | 1999-01-09 | 1999-12-23 | Crystalline bis((E)-7- ( 4-(4- fluorophenyl)- 6-isopropyl-2- [methyl (methylsulfonyl) amino) pyrimidin -5-yl) (3R,5S)-3, 5-dihydroxyhept -6-enoic acid]calcium salt |
IL14397799A IL143977A0 (en) | 1999-01-09 | 1999-12-23 | Crystalline bis [(e)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl (methylsulphonyl) amino] pyrimidin-5-yl] (3r,5s)-3,5-dihydroxyhept-6-enoic acid] calcium salt |
IS5977A IS2410B (en) | 1999-01-09 | 2001-06-22 | Crystalline bis [(E) -7- [4- (4-fluorophenyl) -6-isopropyl-2- [methyl (methylsulfonyl) amino] pyrimidin-5-yl] (3R, 5S) -3,5-dihydroxyhept-6 -enoic acid] calcium salt |
NO20013368A NO320189B1 (en) | 1999-01-09 | 2001-07-06 | Crystalline bis ((E) -7- (4- (4-fluorophenyl) -6-isopropyl-2- (methyl (methylsulfonyl) amino) pyrimidin-5-yl) (3R, 5S) -3,5-dihydroxyhept-6 calcium salt, method of preparation and use thereof, and pharmaceutical composition. |
HK02102104.7A HK1040989B (en) | 1999-01-09 | 2002-03-19 | Crystalline bis[(e)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl) amino]pyrimidin -5-yl](3r,5s)-3, 5-dihydroxyhept-6-enoic acid]calcium salt |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9900339.4 | 1999-01-09 | ||
GBGB9900339.4A GB9900339D0 (en) | 1999-01-09 | 1999-01-09 | Chemical compounds |
Related Child Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/869,462 A-371-Of-International US6589959B1 (en) | 1999-01-09 | 1999-12-23 | Crystalline bis[(e)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3R,5S)-3,5-dihydroxyhept-6-enoic acid]calcium salt |
US10/410,650 Division US20040009997A1 (en) | 1999-01-09 | 2003-04-10 | Crystalline bis[(E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl (methylsulfonyl) amino]pyrimidin -5-yl] (3R,5S)-3, 5-dihydroxyhept -6-enoic acid]calcium salt |
Publications (1)
Publication Number | Publication Date |
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WO2000042024A1 true WO2000042024A1 (en) | 2000-07-20 |
Family
ID=10845719
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB1999/004439 WO2000042024A1 (en) | 1999-01-09 | 1999-12-23 | Crystalline bis[(e)-7- [ 4-(4- fluorophenyl)- 6-isopropyl-2- [methyl (methylsulfonyl) amino] pyrimidin -5-yl] (3r,5s)-3, 5-dihydroxyhept -6-enoic acid]calcium salt |
Country Status (32)
Country | Link |
---|---|
US (2) | US6589959B1 (en) |
EP (1) | EP1144389B1 (en) |
JP (2) | JP4996786B2 (en) |
KR (1) | KR100645858B1 (en) |
CN (1) | CN1213033C (en) |
AT (1) | ATE282027T1 (en) |
AU (1) | AU762909B2 (en) |
BR (1) | BR9916786A (en) |
CA (1) | CA2356212C (en) |
CZ (1) | CZ299843B6 (en) |
DE (1) | DE69921855T2 (en) |
DK (1) | DK1144389T3 (en) |
EE (1) | EE05033B1 (en) |
ES (1) | ES2232194T3 (en) |
GB (1) | GB9900339D0 (en) |
HK (1) | HK1040989B (en) |
HU (1) | HU228116B1 (en) |
ID (1) | ID29432A (en) |
IL (1) | IL143977A0 (en) |
IN (2) | IN213326B (en) |
IS (1) | IS2410B (en) |
MX (1) | MX223771B (en) |
NO (1) | NO320189B1 (en) |
NZ (1) | NZ512560A (en) |
PL (1) | PL201800B1 (en) |
PT (1) | PT1144389E (en) |
RU (1) | RU2236404C2 (en) |
SI (1) | SI1144389T1 (en) |
SK (1) | SK285807B6 (en) |
TR (1) | TR200101894T2 (en) |
WO (1) | WO2000042024A1 (en) |
ZA (1) | ZA200105187B (en) |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2001060804A1 (en) * | 2000-02-15 | 2001-08-23 | Astrazeneca Ab | Crystalline salts of 7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl]-(3r,5s)-3,5-dihydroxyhept-6-enoic acid |
US6316460B1 (en) | 2000-01-26 | 2001-11-13 | Astrazeneca Ab | Pharmaceutical compositions |
WO2003011309A2 (en) * | 2001-07-20 | 2003-02-13 | S.K. Enterprise Gmbh | Pharmaceutical composition for treating hypercholesterolaemia |
WO2004014872A1 (en) * | 2002-08-13 | 2004-02-19 | Astrazeneca Uk Limited | Process for preparing the calcium salt of rosuvastatin |
WO2004108691A1 (en) * | 2003-06-05 | 2004-12-16 | Astrazeneca Uk Limited | Improved production of rosuvastatin calcium salt |
WO2005023779A1 (en) * | 2003-09-10 | 2005-03-17 | Astrazeneca Uk Limited | Crystalline form of bis [(e)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3r,5s)-3,5-dihydroxyhept-6 -enoicacid] calcium salt |
WO2005068435A1 (en) * | 2004-01-16 | 2005-07-28 | Zentiva, A. S. | A method of preparation of the hemi-calcium salt of (e)-7-[4-(4-fluorophenyl)-6-isopropyl-2- [methyl(methylsulfonvl)aminolpyrimidin-5-yl](3r,5s)-3,5-, dihvdroxy-6-heptenoic acid |
WO2005077916A1 (en) * | 2004-01-19 | 2005-08-25 | Ranbaxy Laboratories Limited | Salts of hmg-coa reductase inhibitors and use thereof |
WO2006079611A1 (en) * | 2005-01-31 | 2006-08-03 | Ciba Specialty Chemicals Holding Inc. | Crystalline forms of rosuvastatin calcium salt |
WO2007000121A1 (en) * | 2005-06-29 | 2007-01-04 | Zentiva, A.S. | A method for the production of the hemi-calcium salt of (e)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]pyrimidin-5-yl](3r,5s)-3,5-dihydroxyhept-6-enoic acid |
WO2008015563A2 (en) * | 2006-08-04 | 2008-02-07 | Glenmark Pharmaceuticals Limited | Salts of rosuvastatin and processes for their preparation |
WO2009143776A1 (en) | 2008-05-27 | 2009-12-03 | 常州制药厂有限公司 | Preparation method of rosuvastatin calcium and its intermediates |
US7932263B2 (en) | 2003-09-26 | 2011-04-26 | Astrazeneca Ab | Therapeutic treatment |
WO2012069394A1 (en) | 2010-11-22 | 2012-05-31 | Basf Se | Multicomponent system of rosuvastatin calcium salt and sorbitol |
EP2508514A1 (en) | 2005-06-24 | 2012-10-10 | LEK Pharmaceuticals d.d. | Process for preparing amorphous rosuvastatin calcium free of impurities |
WO2012143308A1 (en) | 2011-04-18 | 2012-10-26 | Basf Se | Multicomponent crystalline system of rosuvastatin calcium salt and vanillin |
US20130018065A1 (en) * | 2009-12-16 | 2013-01-17 | Lek Pharmaceuticals D.D. | Processes for the preparation of key intermediate for the synthesis of rosuvastatin or pharmaceutically acceptable salts thereof |
US9371291B2 (en) | 2003-10-24 | 2016-06-21 | Astrazeneca Uk Limited | Process for the manufacture of the calcium salt of rosuvastatin (E)-7-[4-(4-fluorophenyl)-6-isopropyl-2-[methyl(methylsulfonyl)amino]-pyrimidin-5-yl](3R,5S)-3,5-Dihydroxyhept-6-enoic acid and crystalline intermediates thereof |
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CN105837516B (en) * | 2016-05-16 | 2018-07-10 | 山东新时代药业有限公司 | A kind of rosuvastain calcium crystal form and preparation method thereof |
WO2022228551A1 (en) * | 2021-04-30 | 2022-11-03 | 江苏恒瑞医药股份有限公司 | Administration scheme for thrombopoietin receptor agonist |
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