US20060142582A1 - Crystalline forms of pitavastatin calcium - Google Patents

Crystalline forms of pitavastatin calcium Download PDF

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Publication number
US20060142582A1
US20060142582A1 US10/544,752 US54475205A US2006142582A1 US 20060142582 A1 US20060142582 A1 US 20060142582A1 US 54475205 A US54475205 A US 54475205A US 2006142582 A1 US2006142582 A1 US 2006142582A1
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US
United States
Prior art keywords
polymorph
quinolin
fluorophenyl
dihydroxy
cyclopropyl
Prior art date
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Abandoned
Application number
US10/544,752
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English (en)
Inventor
Paul Van Der Schaaf
Fritz Blatter
Martin Szelagiewicz
Kai-Uwe Schoning
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Nissan Chemical Corp
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Ciba Specialty Chemicals Corp
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First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=32865094&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=US20060142582(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Ciba Specialty Chemicals Corp filed Critical Ciba Specialty Chemicals Corp
Assigned to CIBA SPECIALTY CHEMICALS CORP. reassignment CIBA SPECIALTY CHEMICALS CORP. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: SCHONING, KAI-UWE, BLATTER, FRITZ, SZELAGIEWICZ, MARTIN, VAN DER SCHAAF, PAUL ADRIAAN
Publication of US20060142582A1 publication Critical patent/US20060142582A1/en
Assigned to NISSAN CHEMICAL INDUSTRIES LTD. reassignment NISSAN CHEMICAL INDUSTRIES LTD. CONDITIONAL ASSIGNMENT (SEE DOCUMENT FOR DETAILS). Assignors: CIBA SPECIALTY CHEMICALS CORPORATION
Priority to US12/331,086 priority Critical patent/US20090182008A1/en
Priority to US13/280,431 priority patent/US20120101126A1/en
Priority to US13/664,498 priority patent/US8557993B2/en
Priority to US14/016,399 priority patent/US8853405B2/en
Priority to US14/468,572 priority patent/US20140364614A1/en
Priority to US14/872,255 priority patent/US20160024010A1/en
Priority to US15/284,561 priority patent/US20170022163A1/en
Priority to US15/725,397 priority patent/US20180029987A1/en
Priority to US16/053,879 priority patent/US20180346425A1/en
Priority to US16/400,566 priority patent/US20190256469A1/en
Priority to US16/740,516 priority patent/US20200148644A1/en
Priority to US17/029,692 priority patent/US20210002227A1/en
Priority to US17/675,413 priority patent/US20220169614A1/en
Priority to US18/336,332 priority patent/US20230322680A1/en
Abandoned legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

Definitions

  • the present invention is directed to new crystalline forms and the amorphous form of Pitavastatin calcium, processes for the preparation thereof and pharmaceutical compositions comprising these forms.
  • the present invention relates to new crystalline forms and the amorphous form of Pitavastatin calcium.
  • Pitavastatin is also known by the names NK-104, Itavastatin and Nisvastatin.
  • Pitavastatin calcium is known by the chemical name: (3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy-6(E)-heptanoic acid hemicalcium salt.
  • Pitavastatin calcium has the following formula:
  • the amorphous form is encountered. Different polymorphs, pseudopolymorphs or the amorphous form differ in their physical properties such as melting point, solubility etc. These can appreciably influence pharmaceutical properties such as dissolution rate and bioavailability. It is also economically desirable that the product is stable for extended periods of time without the need for specialized storage conditions. It is therefore important to evaluate polymorphism of drug substances. Furthermore, the discovery of new crystalline polymorphic forms of a drug enlarge the repertoire of materials that a formulation scientist has with which to design a pharmaceutical dosage form of a drug with a targeted release profile or other desired characteristics. We now have surprisingly found novel crystalline forms of Pitavastatin calcium, herein designated as form A, B, C, D, E and F, and the amorphous form of Pitavastatin calcium.
  • the present invention is directed to the polymorphic Forms A, B, C, D, E and F, and the amorphous form of Pitavastatin calcium salt (2:1).
  • Another object of the invention is a crystalline polymorph of (3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy-6(E)-heptanoic acid hemicalcium salt, herein designated as Form B, which exhibits a characteristic X-ray powder diffraction pattern with characteristic peaks expressed in d-values ( ⁇ ) and in 2 ⁇ as given in Table 2. TABLE 2 d-spacings and 2 ⁇ angles for Form B. d-spacing [ ⁇ ] Angle [2 ⁇ ] Rel.
  • Another object of the invention is a crystalline polymorph of (3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy-6(E)heptanoic acid hemicalcium salt, herein designated as Form C, which exhibits a characteristic X-ray powder diffraction pattern with characteristic peaks expressed in d-values ( ⁇ ) and in 2 ⁇ as given in Table 3. TABLE 3 d-spacings and 2 ⁇ angles for Form C. d-spacing [ ⁇ ] Angle [2 ⁇ ] Rel.
  • Another object of the invention is a crystalline polymorph of (3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy-6(E)-heptanoic acid hemicalcium salt, herein designated as Form D, which exhibits a characteristic X-ray powder diffraction pattern with characteristic peaks expressed in d-values ( ⁇ ) and in 2 ⁇ as given in Table 4. TABLE 4 d-spacings and 2 ⁇ angles for Form D. d-spacing [ ⁇ ] Angle [2 ⁇ ] Rel.
  • Another object of the invention is a crystalline polymorph of (3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy-6(E) heptanoic acid hemicalcium salt, herein designated as Form E, which exhibits a characteristic X-ray powder diffraction pattern with characteristic peaks expressed in d-values ( ⁇ ) and in 2 ⁇ as given in Table 5. TABLE 5 d-spacings and 2 ⁇ angles for Form E. d-spacing [ ⁇ ] Angle [2 ⁇ ] Rel.
  • Another object of the invention is a crystalline polymorph of (3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy-6(E)-heptanoic acid hemicalcium salt, herein designated as Form F, which exhibits a characteristic X-ray powder diffraction pattern with characteristic peaks expressed in d-values ( ⁇ ) and in 2 ⁇ as given in Table 6. TABLE 6 d-spacings and 2 ⁇ angles for Form F. d-spacing [ ⁇ ] Angle [2 ⁇ ] Rel.
  • Another object of the invention is the amorphous form of (3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy-6(E)-heptanoic acid hemicalcium salt which exhibits characteristic X-ray powder diffraction patterns as depicted in FIG. 7 .
  • Powder X-ray diffraction is performed on a Philips 1710 powder X-ray diffractometer using Cu k( ⁇ 1) radiation (1.54060 ⁇ ); 2 ⁇ angles are recorded with an experimental error of ⁇ 0.1-0.2°.
  • a discussion of the theory of X-ray powder diffraction patterns can be found in “X-ray diffraction procedures” by H. P. Klug and L. E. Alexander, J. Wiley, New York (1974).
  • the present invention is directed to processes for the preparation of Form A, B, C, D, E and F, and the amorphous form of Pitavastatin calcium.
  • Form A can be generally prepared from Pitavastatin sodium upon reaction with CaCl 2 in an aqueous reaction medium.
  • Form A of the invention may also be obtained in situ from the free acid ((3R,5S)-7-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]-3,5-dihydroxy-6(E)-heptanoic acid) or the corresponding lactone with Ca(OH) 2 , advantageously also in an aqueous reaction medium.
  • the aqueous reaction medium usually contains at least 80% b.w. of water; preferably it is water or water containing minor amounts of solvents and/or reactants from previous steps.
  • Form A may contain up to 15% water, preferably about 3 to 12%, more preferably 9 to 11% of water.
  • Form B can be generally prepared by suspending form A in ethanol containing water as a co solvent.
  • the amount of water is preferably about 1 to 50%.
  • Form C can be generally prepared by suspending form A in isopropanol containing water as a co solvent.
  • the amount of water is preferably about 1 to 50%, especially 1 to 20% and more preferably about 5%.
  • Form C can also be prepared from a mixture of isopropanol and a ketone solvent, containing water as a co solvent.
  • the ketone solvent is acetone, and the amount of ketone solvent are about 1 to 30%, more preferably about 10%.
  • the amount of water is preferably about 1 to 20%, more preferably about 5%.
  • Form D can be generally prepared by suspending form A in absolute ethanol.
  • Form E can be generally prepared by suspending form A in 1,4-dioxane containing water as a co solvent.
  • the amount of water is preferably about 1 to 50%.
  • Form F can be generally prepared by suspending form A in methanol containing water as a co solvent.
  • the amount of water is preferably about 1 to 50%.
  • seeding crystals of the desired crystalline form may be added to the reaction mixture. Preferably small amounts are about 1 to 20 weight %, more preferably about 5 weight %. Seeding crystals may be added before or, where appropriate, after the step initiating the crystallization (e.g. cooling, addition of non-solvent etc. as described above). Addition before initiating the crystallization is of specific technical interest.
  • the amorphous form can be generally prepared by addition of a non-solvent to a concentrated solution of Pitavastatin calcium in an organic solvent.
  • non-solvent may be taken for example heptane or methyl tert-butyl ether, whereas examples for the organic solvent are 1,4-dioxane, tetrahydrofuran and ethyl methyl ketone. It is preferable that the non-solvent and solvent are miscible.
  • the amorphous form can also be prepared by lyophilization of an aqueous solution of Pitavastatin calcium.
  • Preparations of polymorphic forms A, B, C, D, E, F as well as the amorphous form are usually done in substantially pure reaction systems, essentially consisting of the educt specified, preferably in substantially crystalline form, and solvents and/or non-solvents as given above.
  • Another object of the present invention are processes for the preparation of crystalline forms of Pitavastatin calcium essentially free of residual organic solvent.
  • the present invention is related to processes for the preparation of crystalline forms of Pitavastatin calcium essentially free of residual organic solvent by exposing the crystalline form of Pitavastatin calcium to an atmosphere with a defined relative air humidity.
  • the present invention is directed to a process for the preparation of any crystalline form or amorphous form of Pitavastatin calcium which is essentially free of residual organic solvent.
  • These can, for example, be prepared by exposing the crystalline form or amorphous form to an atmosphere with a relative air humidity of 5 to 100%.
  • these are prepared by exposure to an inert gas stream with a defined relative air humidity to exchange residual organic solvent with water.
  • compositions comprising an effective amount of crystalline polymorphic Form A, B, C, D, E or F or the amorphous form of Pitavastatin calcium, and a pharmaceutically acceptable carrier.
  • polymorphic forms may be used as single component or as mixtures with other crystalline forms or the amorphous form.
  • novel polymorphic forms and amorphous form of Pitavastatin calcium it is preferred that these contain 25-100% by weight, especially 50-100% by weight, of at least one of the novel forms, based on the total amount of Pitavastatin calcium.
  • such an amount of the novel polymorphic forms or amorphous form of Pitavastatin calcium is 75-100% by weight especially 90-100% by weight. Highly preferred is an amount of 95-100% by weight.
  • compositions of the invention include powders, granulates, aggregates and other solid compositions comprising at least one of the novel forms.
  • compositions that are contemplated by the present invention may further include diluents, such as cellulose-derived materials like powdered cellulose, microcrystalline cellulose, microfine cellulose, methyl cellulose, ethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, hydroxypropylmethyl cellulose, carboxymethyl, cellulose salts and other substituted and unsubstituted celluloses; starch; pregelatinized starch; inorganic diluents like calcium carbonate and calcium diphosphate and other diluents known to the pharmaceutical industry.
  • suitable diluents include waxes, sugars and sugar alcohols like mannitol and sorbitol, acrylate polymers and copolymers, as well as pectin, dextrin and gelatin.
  • excipients that are within the contemplation of the present invention include binders, such as acacia gum, pregelatinized starch, sodium alginate, glucose and other binders used in wet and dry granulation and direct compression tableting processes.
  • binders such as acacia gum, pregelatinized starch, sodium alginate, glucose and other binders used in wet and dry granulation and direct compression tableting processes.
  • Excipients that also may be present in the solid compositions further include disintegrants like sodium starch glycolate, crospovidone, low-substituted hydroxypropyl cellulose and others.
  • excipients may include tableting lubricants like magnesium and calcium stearate and sodium stearyl fumarate; flavorings; sweeteners; preservatives; pharmaceutically acceptable dyes and glidants such as silicon dioxide.
  • the dosages include dosages suitable for oral, buccal, rectal, parenteral (including subcutaneous, intramuscular, and intravenous), inhalant and ophthalmic administration.
  • parenteral including subcutaneous, intramuscular, and intravenous
  • inhalant and ophthalmic administration are examples of the most suitable route in any given case.
  • oral the most preferred route of the present invention is oral.
  • the dosages may be conveniently presented in unit dosage form and prepared by any of the methods well-known in the art of pharmacy.
  • Dosage forms include solid dosage forms, like tablets, powders, capsules, suppositories, sachets, troches and losenges as well as liquid suspensions and elixirs. While the description is not intended to be limiting, the invention is also not intended to pertain to true solutions of Pitavastatin calcium whereupon the properties that distinguish the solid forms of Pitavastatin calcium are lost. However, the use of the novel forms to prepare such solutions is considered to be within the contemplation of the invention.
  • Capsule dosages will contain the solid composition within a capsule which may be made of gelatin or other conventional encapsulating material.
  • Tablets and powders may be coated. Tablets and powders may be coated with an enteric coating.
  • the enteric coated powder forms may have coatings comprising phthalic acid cellulose acetate, hydroxypropylmethyl-cellulose phthalate, polyvinyl alcohol phthalate, carboxymethylethylcellulose, a copolymer of styrene and maleic acid, a copolymer of methacrylic acid and methyl methacrylate, and like materials, and if desired, they may be employed with suitable plasticizers and/or extending agents.
  • a coated tablet may have a coating on the surface of the tablet or may be a tablet comprising a powder or granules with an enteric-coating.
  • Preferred unit dosages of the pharmaceutical compositions of this invention typically contain from 0.5 to 100 mg of the novel Pitavastatin calcium forms or mixtures thereof with each other or other forms of Pitavastatin calcium. More usually, the combined weight of the Pitavastatin calcium forms of a unit dosage are from 2.5 mg to 80 mg, for example 5, 10, 20 or 40 mg.
  • the aqueous phase was separated and once extracted with 20 ml of methyl tert-butyl ether. To this aqueous solution were added a solution of 0.58 gr CaCl 2 in 80 ml of water over a period of 1 hour. The resulting suspension was stirred for about 16 hours at room temperature. The suspension was filtered and the obtained solid was dried at 40° C. and 50 mbar for about 16 hours.
  • the obtained product is crystal Form A which is characterized by an X-ray powder diffraction pattern as shown in FIG. 1 . Further characterization of the obtained Form A by thermogravimetry coupled with FT-IR spectroscopy revealed a water content of about 10%. Differential scanning calorimetry revealed a melting point of 95° C.
  • FIG. 1 is a characteristic X-ray powder diffraction pattern for Form A.
  • FIG. 2 is a characteristic X-ray powder diffraction pattern for Form B.
  • FIG. 3 are two characteristic X-ray powder diffraction patterns for Form C.
  • FIG. 4 is a characteristic X-ray powder diffraction pattern for Form D.
  • FIG. 5 is a characteristic X-ray powder diffraction pattern for Form E.
  • FIG. 6 is a characteristic X-ray powder diffraction pattern for Form F.
  • FIG. 7 are two characteristic X-ray powder diffraction patterns for the amorphous form.

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US10/544,752 2003-02-12 2004-02-02 Crystalline forms of pitavastatin calcium Abandoned US20060142582A1 (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
US12/331,086 US20090182008A1 (en) 2003-02-12 2008-12-09 Crystalline forms of pitavastatin calcium
US13/280,431 US20120101126A1 (en) 2003-02-12 2011-10-25 Crystalline forms of pitavastatin calcium
US13/664,498 US8557993B2 (en) 2003-02-12 2012-10-31 Crystalline forms of pitavastatin calcium
US14/016,399 US8853405B2 (en) 2003-02-12 2013-09-03 Crystalline forms of pitavastatin calcium
US14/468,572 US20140364614A1 (en) 2003-02-12 2014-08-26 Crystalline forms of pitavastatin calcium
US14/872,255 US20160024010A1 (en) 2003-02-12 2015-10-01 Crystalline forms of pitavastatin calcium
US15/284,561 US20170022163A1 (en) 2003-02-12 2016-10-04 Crystalline forms of pitavastatin calcium
US15/725,397 US20180029987A1 (en) 2003-02-12 2017-10-05 Crystalline forms of pitavastatin calcium
US16/053,879 US20180346425A1 (en) 2003-02-12 2018-08-03 Crystalline forms of pitavastatin calcium
US16/400,566 US20190256469A1 (en) 2003-02-12 2019-05-01 Crystalline forms of pitavastatin calcium
US16/740,516 US20200148644A1 (en) 2003-02-12 2020-01-13 Crystalline forms of pitavastatin calcium
US17/029,692 US20210002227A1 (en) 2003-02-12 2020-09-23 Crystalline forms of pitavastatin calcium
US17/675,413 US20220169614A1 (en) 2003-02-12 2022-02-18 Crystalline forms of pitavastatin calcium
US18/336,332 US20230322680A1 (en) 2003-02-12 2023-06-16 Crystalline forms of pitavastatin calcium

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP03405080.7 2003-02-12
EP03405080 2003-02-12
PCT/EP2004/050066 WO2004072040A1 (en) 2003-02-12 2004-02-02 Crystalline forms of pitavastatin calcium

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PCT/EP2004/050066 A-371-Of-International WO2004072040A1 (en) 2003-02-12 2004-02-02 Crystalline forms of pitavastatin calcium

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US12/331,086 Continuation US20090182008A1 (en) 2003-02-12 2008-12-09 Crystalline forms of pitavastatin calcium
US12/331,066 Continuation US20090084929A1 (en) 2003-02-12 2008-12-09 Machine Stand

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US20060142582A1 true US20060142582A1 (en) 2006-06-29

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US10/544,752 Abandoned US20060142582A1 (en) 2003-02-12 2004-02-02 Crystalline forms of pitavastatin calcium
US12/331,086 Abandoned US20090182008A1 (en) 2003-02-12 2008-12-09 Crystalline forms of pitavastatin calcium
US13/280,431 Abandoned US20120101126A1 (en) 2003-02-12 2011-10-25 Crystalline forms of pitavastatin calcium
US13/664,498 Expired - Lifetime US8557993B2 (en) 2003-02-12 2012-10-31 Crystalline forms of pitavastatin calcium
US14/016,399 Expired - Lifetime US8853405B2 (en) 2003-02-12 2013-09-03 Crystalline forms of pitavastatin calcium
US14/468,572 Abandoned US20140364614A1 (en) 2003-02-12 2014-08-26 Crystalline forms of pitavastatin calcium
US14/872,255 Abandoned US20160024010A1 (en) 2003-02-12 2015-10-01 Crystalline forms of pitavastatin calcium
US15/284,561 Abandoned US20170022163A1 (en) 2003-02-12 2016-10-04 Crystalline forms of pitavastatin calcium
US15/725,397 Abandoned US20180029987A1 (en) 2003-02-12 2017-10-05 Crystalline forms of pitavastatin calcium
US16/053,879 Abandoned US20180346425A1 (en) 2003-02-12 2018-08-03 Crystalline forms of pitavastatin calcium
US16/400,566 Abandoned US20190256469A1 (en) 2003-02-12 2019-05-01 Crystalline forms of pitavastatin calcium
US16/740,516 Abandoned US20200148644A1 (en) 2003-02-12 2020-01-13 Crystalline forms of pitavastatin calcium
US17/029,692 Abandoned US20210002227A1 (en) 2003-02-12 2020-09-23 Crystalline forms of pitavastatin calcium
US17/675,413 Abandoned US20220169614A1 (en) 2003-02-12 2022-02-18 Crystalline forms of pitavastatin calcium
US18/336,332 Pending US20230322680A1 (en) 2003-02-12 2023-06-16 Crystalline forms of pitavastatin calcium

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Application Number Title Priority Date Filing Date
US12/331,086 Abandoned US20090182008A1 (en) 2003-02-12 2008-12-09 Crystalline forms of pitavastatin calcium
US13/280,431 Abandoned US20120101126A1 (en) 2003-02-12 2011-10-25 Crystalline forms of pitavastatin calcium
US13/664,498 Expired - Lifetime US8557993B2 (en) 2003-02-12 2012-10-31 Crystalline forms of pitavastatin calcium
US14/016,399 Expired - Lifetime US8853405B2 (en) 2003-02-12 2013-09-03 Crystalline forms of pitavastatin calcium
US14/468,572 Abandoned US20140364614A1 (en) 2003-02-12 2014-08-26 Crystalline forms of pitavastatin calcium
US14/872,255 Abandoned US20160024010A1 (en) 2003-02-12 2015-10-01 Crystalline forms of pitavastatin calcium
US15/284,561 Abandoned US20170022163A1 (en) 2003-02-12 2016-10-04 Crystalline forms of pitavastatin calcium
US15/725,397 Abandoned US20180029987A1 (en) 2003-02-12 2017-10-05 Crystalline forms of pitavastatin calcium
US16/053,879 Abandoned US20180346425A1 (en) 2003-02-12 2018-08-03 Crystalline forms of pitavastatin calcium
US16/400,566 Abandoned US20190256469A1 (en) 2003-02-12 2019-05-01 Crystalline forms of pitavastatin calcium
US16/740,516 Abandoned US20200148644A1 (en) 2003-02-12 2020-01-13 Crystalline forms of pitavastatin calcium
US17/029,692 Abandoned US20210002227A1 (en) 2003-02-12 2020-09-23 Crystalline forms of pitavastatin calcium
US17/675,413 Abandoned US20220169614A1 (en) 2003-02-12 2022-02-18 Crystalline forms of pitavastatin calcium
US18/336,332 Pending US20230322680A1 (en) 2003-02-12 2023-06-16 Crystalline forms of pitavastatin calcium

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US (15) US20060142582A1 (zh)
EP (3) EP3299359A1 (zh)
JP (13) JP5192147B2 (zh)
CN (3) CN101219992B (zh)
AU (1) AU2004212160B2 (zh)
CA (2) CA2513837A1 (zh)
DE (1) DE202004021379U1 (zh)
PL (1) PL376557A1 (zh)
TW (4) TW201213311A (zh)
WO (1) WO2004072040A1 (zh)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20070173536A1 (en) * 2004-02-06 2007-07-26 Ciba Specialty Chemicals Holding Inc. Crystalline forms of zolmitriptan
US20080194604A1 (en) * 2005-01-31 2008-08-14 Fritz Blatter Crystalline Forms Of Rosuvastatin Calcium Salt

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2513837A1 (en) * 2003-02-12 2004-08-26 Paul Adriaan Van Der Schaaf Crystalline forms of pitavastatin calcium
TWI328006B (en) * 2003-12-26 2010-08-01 Nissan Chemical Ind Ltd Crystal form of quinoline compound and process for its production
AU2013204129C1 (en) * 2003-12-26 2017-03-02 Nissan Chemical Industries, Ltd. Crystal Form of Quinoline Compound and Process for its Production
US20120022102A1 (en) 2010-01-20 2012-01-26 Cadila Healthcare Limited Method for preparation of pitavastatin and its pharmaceutical acceptable salts thereof
JP2013536219A (ja) 2010-08-25 2013-09-19 カディラ・ヘルスケア・リミテッド ピタバスタチンカルシウムおよびその調製方法
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