WO1996020939A1 - POLYMORFOS B Y C DE MONONITRATO DE 1-[2,4-DICLORO-β-[(7-CLOROBENZO[b]TIEN-3-IL)METOXI]FENETIL]IMIDAZOL - Google Patents

POLYMORFOS B Y C DE MONONITRATO DE 1-[2,4-DICLORO-β-[(7-CLOROBENZO[b]TIEN-3-IL)METOXI]FENETIL]IMIDAZOL Download PDF

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Publication number
WO1996020939A1
WO1996020939A1 PCT/ES1995/000001 ES9500001W WO9620939A1 WO 1996020939 A1 WO1996020939 A1 WO 1996020939A1 ES 9500001 W ES9500001 W ES 9500001W WO 9620939 A1 WO9620939 A1 WO 9620939A1
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polymorph
mononitrate
chlorobenzo
thien
dichloro
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PCT/ES1995/000001
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English (en)
French (fr)
Inventor
Rafael Foguet Ambros
Lluis Anglada Burniol
José A. ORTIZ HERNANDEZ
Aurelio SACRISTAN MUÑOZ
Josep María CASTELLO BARENYS
Manuel Mauricio RAGA CARREÑO
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Ferrer Internacional SA
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Ferrer Internacional SA
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Priority to DE69503364T priority Critical patent/DE69503364T2/de
Priority to CA002184411A priority patent/CA2184411C/en
Priority to EP95905144A priority patent/EP0748806B1/en
Priority to US08/702,536 priority patent/US5939555A/en
Priority to KR1019960704405A priority patent/KR100336642B1/ko
Priority to DK95905144T priority patent/DK0748806T3/da
Priority to PCT/ES1995/000001 priority patent/WO1996020939A1/es
Priority to AU13872/95A priority patent/AU691234B2/en
Priority to JP52074296A priority patent/JP3250809B2/ja
Priority to ES95905144T priority patent/ES2120720T3/es
Application filed by Ferrer Internacional SA filed Critical Ferrer Internacional SA
Priority to NZ278402A priority patent/NZ278402A/en
Publication of WO1996020939A1 publication Critical patent/WO1996020939A1/es
Priority to NO19963291A priority patent/NO310915B1/no
Priority to FI963392A priority patent/FI111366B/fi
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
    • C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
    • C07H19/16—Purine radicals
    • C07H19/20—Purine radicals with the saccharide radical esterified by phosphoric or polyphosphoric acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids

Definitions

  • the present invention relates to new Mononi Polymorphs B and C while 1- [2,4-dichloro- ⁇ - [(7-chlorobenzo [Jb] thien-3-yl) methoxy] phenethyl] imidazole, a known compound as Sertaconazole Mononitrate (WHO).
  • Figure 1 depicts the IR spectrum of Sertaconazole Mononitrate Polymorph B.
  • FIG. 2 depicts the "Differential Scanning Calorimetry” (DSC) Thermogram of Polymorph B of Sertaconazole Mononitrate.
  • Figure 3 depicts the X-ray diffractogram of Sertaconazole Mononitrate Polymorph B.
  • Figure 4 depicts the IR spectrum of Sertaconazole Mononitrate Polymorph C.
  • Figure 5 represents the "Differential Scanning Calorimetry” (DSC) Thermogram of Polymorph C of Sertaconazole Mononitrate.
  • Figure 6 depicts the X-ray diffractogram of Sertaconazole Mononitrate Polymorph C.
  • Figure 7 represents the IR spectrum of the Polymorph A of Sertaconazole Mononitrate.
  • Figure 8 depicts the "Differential Scanning Calorimetry” (DSC) Thermogram of Sertaconazole Mononitrate Polymorph A.
  • Figure 9 depicts the X-ray diffractogram of Sertaconazole Mononitrate Polymorph A.
  • the compound [1- [2,4-dichloro- ⁇ - [(7- chlorobenzo [Jb] thien-3-yl) methoxy] phenethyl] imidazole mononitrate is used in Therapeutics as an antifungal.
  • the preparation of this compound is described in EP 151,477.
  • Sertaconazole Mononitrate presents two new polymorphs, called B and C, which respectively present melting points 163-164 ° C and 164.5-165.5 * 0. This application provides a process to obtain selectively each of the two polymorphs B and C of Sertaconazole Mononitrate.
  • Polymorphs B and C of Sertaconazole Mononitrate have different physical properties in relation to the original polymorph A.
  • polymorph B has a greater stability than polymorph A against moderate contributions of external energy, such as screening and homogenization processes, making it suitable for the preparation of solid forms of topical application, such as powders.
  • polymorph C it can be said that it is even more stable than B versus external energy inputs, so it can be advantageously used in processes that require higher energy inputs, such as compression processes, so it is suitable for tablet preparation in general.
  • the formulations to be prepared are liquid, the use of one form or another is indistinct since the characteristics of the solid state are lost in solution.
  • polymorphs B and C of Sertaconazole Mononitrate mixed with pharmaceutically acceptable excipients can be administered orally to humans and animals in the form of capsules, syrups, solutions, powders, etc., by injectable route, rectally or vaginally - intrauterine in the form of ovules, ointments, creams, pessaries, lotions, etc., at daily doses between 100 and 800 m 9 and P or topically in the form of creams, lotions, ointments, emulsions, solutions, shampoos, gels, etc. at concentrations between 0.1 and 5%.
  • Sertaconazole polymorphs B and C mixed with a diluent or excipient can be applied against agricultural diseases suspended in irrigation waters. They can also be administered by atomization, spraying and dusting or in the form of cream, paste, etc. at a rate of 0.1-15 kg per hectare of soil.
  • Polymorph B of 1- [2,4-dichloro- ⁇ - [(7- chlorobenzo [b] thien-3-yl) methoxy] phenethyl] lmidazole mononitrate Polymorph B of Sertaconazole Mononitrate

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  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
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  • Genetics & Genomics (AREA)
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  • Animal Behavior & Ethology (AREA)
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  • General Chemical & Material Sciences (AREA)
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  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

Se han identificado dos nuevos polimorfos del Mononitrato de 1-[2,4-dicloro-β-[(7-clorobenzo[b]tien-3-il)metoxi]fenetil]imidazol. Se describe un proceso para la obtención de ambos y su uso posterior.

Description

POLIMORFOS B Y C DE MONONITRATO DE 1- 2.4-DICLORO-
-S- r(7-CLOROBENZθrablTIE -3-IL)METOXI]FENETIL1 IMIDAZOL
La presente invención se refiere a nuevos Polimorfos B y C de Mononi rato de 1- [2,4-dicloro-β- [ (7-clorobenzo[Jb] tien- 3-il)metoxi] fenetil] imidazol, compuesto que se conoce como Mononitrato de Sertaconazol (OMS) .
Breve descripción de las figuras
La Figura 1 representa el espectro de IR del Polimorfo B de Mononitrato de Sertaconazol.
La Figura 2 representa el Termograma de "Differential Scanning Calorimetry" (DSC) del Polimorfo B de Mononitrato de Sertaconazol.
La Figura 3 representa el Difractograma de Rayos X del Polimorfo B de Mononitrato de Sertaconazol.
La Figura 4 representa el espectro de IR del Polimorfo C de Mononitrato de Sertaconazol.
La Figura 5 representa el Termograma de "Differential Scanning Calorimetry" (DSC) del Polimorfo C de Mononitrato de Sertaconazol.
La Figura 6 representa el Difractograma de Rayos X del Polimorfo C de Mononitrato de Sertaconazol.
La Figura 7 representa el espectro de IR del Polimorfo A de Mononitrato de Sertaconazol.
La Figura 8 representa el Termograma de "Differential Scanning Calorimetry" (DSC) del Polimorfo A de Mononitrato de Sertaconazol. La Figura 9 representa el Difractograma de Rayos X del Polimorfo A de Mononitrato de Sertaconazol.
Descripción detallada de la Invención
El compuesto Mononitrato de 1- [2,4-dicloro-β- [ (7- clorobenzo[Jb] tien-3-il)metoxi] fenetil] imidazol se utiliza en Terapéutica como antifúngico. La obtención de este compuesto está descrita en la patente EP 151.477. Los solicitantes han descubierto que Mononitrato de Sertaconazol presenta dos nuevos polimorfos, llamados B y C, los cuales presentan respectivamente los puntos de fusión 163-164°C y 164,5- 165,5*0. La presente solicitud suministra un proceso para obtener selectivamente cada uno de los dos polimorfos B y C de Mononitrato de Sertaconazol. En la antedicha patente se obtiene Mononitrato de Sertaconazol con un punto de fusión de 156-157*0, que desde aquí en adelante llamaremos polimorfo A. Pues bien, en el curso de diferentes pruebas de cristalización, los solicitantes han descubierto que si el polimorfo A se recristaliza de etanol absoluto, se obtiene en forma del nuevo polimorfo B, mientras que si se recristaliza de cloroformo, se obtiene como el nuevo polimorfo C. Tal como se ha indicado, los puntos de fusión de los tres polimorfos son muy próximos, pero están bien diferenciados según muestran los espectros de IR, los termogramas de "Differential Scanning Calorimetry" (DSC) y los difractogramas de Rayos X. Para mostrar bien las diferencias de los nuevos polimorfos B y C respecto del original A, se adjuntan también las antedichas tres pruebas (Figuras 7,8,9) de este último.
Los polimorfos B y C de Mononitrato de Sertaconazol presentan distintas propiedades físicas con relación al polimorfo original A. En efecto, el polimorfo B presenta una mayor estabilidad que el polimorfo A frente a aportes moderados de energía externa, tales como procesos de tamización y homogeneización, por lo que es adecuado para la preparación de formas sólidas de aplicación tópica, como por ejemplo polvos. En cuanto al polimorfo C, puede decirse que aún es más estable qμe el B frente a aportes de energía externa, por lo que puede emplearse ventajosamente en procesos que requieran superiores aportes energéticos, tales como procesos de compresión, por lo que es adecuado para la preparación de comprimidos en general. En el caso de que las formulaciones a preparar sean líquidas, el uso de una u otra forma es indistinto puesto que las características propias del estado sólido se pierden en solución.
Además de las formas farmacéuticas citadas en el párrafo precedente, los polimorfos B y C de Mononitrato de Sertaconazol mezclados con los excipientes farmacéuticamente aceptables pueden administrarse por vía oral a humanos y animales en forma de cápsulas, jarabes, soluciones, polvos, etc., por vía inyectable, por vía rectal o vaginal- intrauterina en forma de óvulos, ungüentos, cremas, pesarios, lociones, etc., a dosis diarias comprendidas entre 100 y 800 m9 y Por vía tópica en forma de cremas, lociones, ungüentos, emulsiones, soluciones, champús, geles, etc. a concentraciones comprendidas entre 0,1 y 5 %. De manera análoga, los polimorfos B y C de Sertaconazol mezclados con un diluyente o excipiente, pueden aplicarse contra enfermedades agrícolas suspendidos en las aguas de riego. También pueden administrarse por atomización, pulverización y polvoreado o en forma de crema, pasta, etc. a razón de 0,1-15 kg por hectárea de suelo.
Los siguientes ejemplos ilustran la obtención de las formas B y C de Mononitrato de Sertaconazol y de formulaciones que los contienen. Los ejemplos no se orientan a limitar la amplitud de la invención, según se ha definido, o como se reivindica más adelante.
Polimorfo B de Mononitrato de 1- [2,4-dicloro-β- [(7- clorobenzo [b] tien-3-il)metoxi] fenetil] lmidazol (Polimorfo B de Mononitrato de Sertaconazol)
Se disuelven 10 g de Mononitrato de Sertaconazol (Polimorfo A) en 100 mi de etanol absoluto a reflujo. Se filtra la disolución caliente y se deja cristalizar a temperatura ambiente sin agitación. Se filtra el sólido cristalino formado y se seca. Se obtienen 8,78 g de Polimorfo B de Mononitrato de 1- [2,4-dicloro-β- [ (7-clorobenzo[ ] tien-3- il)metoxi] fenetil] imidazol (Polimorfo B de Mononitrato de Sertaconazol) .
P. f.: 163-164°C Espectro IR (KBr) : Figura 1
Termograma de "Differential Scanning Calorimetry" (DSC) : Figura 2
Difractograma de Rayos X: Figura 3
Ejemplo 2
Polimorfo C de Mononitrato de 1- [2,4-dicloro-β- [ (7- clorobenzo[ ] tien-3-11)metoxi]fenetil]imidazol (Polimorfo C de Mononitrato de Sertaconazol)
Se disuelven 5 g de Mononitrato de Sertaconazol (Polimorfo A) en 150 mi de cloroformo a reflujo. Se filtra la disolución caliente y se deja cristalizar a temperatura ambiente sin agitación. Se filtra el sólido cristalino formado y se seca. Se obtienen 4,2 g de Polimorfo C de Mononitrato de l-[2,4- dicloro-β- [ (7-clorobenzo[Jb] tien-3-il)metoxi] fenetil] imidazol (Polimorfo C de Mononitrato de Sertaconazol) . P. f.: 164,5-165,5*C Espectro IR (KBr) : Figura 4
Termograma de "Differential Scanning Calorimetry" (DSC) : Figura 5
Difractograma de Rayos X: Figura 6
Ejemplo 3
Polvo al 2 % para aplicación tópica Fórmula por 100 g: Polimorfo B de Mononitrato de Sertaconazol .... 2 g
Dióxido de titanio 10 g Caolín 10 g
Talco 78 g
Ejemplo 4 Comprimidos vaginales Fórmula por comprimido vaginal:
Polimorfo C de Mononitrato de Sertaconazol .. 500 mg
Almidón de maíz 90 mg
Aerosil 200 1 mg
Primogel 45 mg Compritol 150 mg
Estearato de magnesio 7,5 mg
Avicel PH-101 csh 1100 mg

Claims

Reivindicaciones lβ) - Un compuesto de nombre químico Mononitrato de 1- [2 , 4 - dicloro - β- [ ( 7 - clorobenzo [¿] tien- 3 - iDmetoxi] fenetil] imidazol como Polimorfo B, caracterizado por obtenerse disolviendo el Polimorfo A en etanol absoluto a reflujo, seguido de filtración de la disolución caliente, cristalización a temperatura ambiente y filtración y por presentar un punto de fusión de 163-164°C.
2*) - Un compuesto de nombre químico Mononitrato de 1- [2 , 4 - dicloro - β - [ ( 7 - clorobenzo [b] tien - 3 - iDmetoxi] fenetil] imidazol como Polimorfo C, caracterizado por obtenerse disolviendo el Polimorfo A en cloroformo a reflujo, seguido de filtración de la disolución caliente, cristalización a temperatura ambiente y filtración y por presentar un punto de fusión de 164, 5-165,5°C.
3") - Un compuesto según la reivindicación 1, teniendo el espectro de IR según muestra la Figura 1, el termograma de
"Differential Scanning Calorimetry" (DSC) según muestra la
Figura 2 y el difractograma de Rayos X según muestra la Figura 3.
4β) - Un compuesto según la reivindicación 2, teniendo el espectro de IR según muestra la Figura 4, el termograma de
"Differential Scanning Calorimetry" (DSC) según muestra la
Figura 5 y el difractograma de Rayos X según muestra la Figura 6.
PCT/ES1995/000001 1995-01-04 1995-01-04 POLYMORFOS B Y C DE MONONITRATO DE 1-[2,4-DICLORO-β-[(7-CLOROBENZO[b]TIEN-3-IL)METOXI]FENETIL]IMIDAZOL Ceased WO1996020939A1 (es)

Priority Applications (13)

Application Number Priority Date Filing Date Title
JP52074296A JP3250809B2 (ja) 1995-01-04 1995-01-04 １−［２，４−ジクロロ−β−［（７−クロロベンゾ［ｂ］チエニ−３−イル）メトキシ］フェネチル］イミダゾール・１硝酸塩の同質異像Ｂ及びＣ
EP95905144A EP0748806B1 (en) 1995-01-04 1995-01-04 PROCESS FOR PREPARING POLYMORPHS B AND C OF 1- 2,4-DICHLORO-BETA-[(7-CHLOROBENZO[b]THIEN-3-YL)METHOXY]PHENETYL]IMIDAZOLE MONONITRATE
US08/702,536 US5939555A (en) 1995-01-04 1995-01-04 Polymorphs B and C of 1- 2,4-dichloro-β- (7-chlorobenzo b!thien-3-yl)methoxy!phenethyl!imidazole mononitrate
KR1019960704405A KR100336642B1 (ko) 1995-01-04 1995-01-04 1-[2,4-디클로로-β-[7-클로로벤조[B]티엔-3-일)메톡시]페네틸]이미다졸모노나이트레이트의폴리모르프B및C의제조방법
DK95905144T DK0748806T3 (da) 1995-01-04 1995-01-04 Fremgangsmåde til fremstilling af polymorf B og C af 1-[2,4-dichlor-beta-[(7-chlorbenzo[b]thien-3-yl)methoxy]phenethyl]imid
PCT/ES1995/000001 WO1996020939A1 (es) 1995-01-04 1995-01-04 POLYMORFOS B Y C DE MONONITRATO DE 1-[2,4-DICLORO-β-[(7-CLOROBENZO[b]TIEN-3-IL)METOXI]FENETIL]IMIDAZOL
AU13872/95A AU691234B2 (en) 1995-01-04 1995-01-04 Process for preparing polymorphs B and C of 1- 2,4-dichloro -beta- (7-chlorobenzo b thien-3-yl)methoxy phenethyl imidazole mononitrate
DE69503364T DE69503364T2 (de) 1995-01-04 1995-01-04 Verfahren zur herstellung von polymorphe b und c von 1-(2,4-dichloro-beta-((7-chloro-benzo(b)thien-3-yl)methoxy)phenethyl) imidazol-mononitrat
CA002184411A CA2184411C (en) 1995-01-04 1995-01-04 Process for preparing polymorphs b and c of 1-[2,4-dichloro-.beta.-[(7-chlorobenzo[b]thien-3-yl)methoxy]phenethyl]imidazole mononitrate
ES95905144T ES2120720T3 (es) 1995-01-04 1995-01-04 Procedimiento de obtencion de los polimeros b y c de mononitrato de 1-(2,4-dicloro-beta-((7-clorobenzo(b)tien-3-il)metoxi)fenetil)imidazol.
NZ278402A NZ278402A (en) 1995-01-04 1995-01-04 Polymorphs of sertaconazole mononitrate (ie 1-[2,4-dichloro-beta-[(7-chlorobenzo[b]thien-3-yl)methoxy]phen ethyl]imidazole mononitrate)
NO19963291A NO310915B1 (no) 1995-01-04 1996-08-07 Fremstilling av Polymorfene B og C av 1-[2,4-diklor-<beta>- [(7-klorbenzo[b]tien-3-yl)metoksy]fenetyl]imidazol. mononitrat
FI963392A FI111366B (fi) 1995-01-04 1996-08-30 Menetelmä 1-[2,4-dikloori-beta-[(7-klooribentso[b]tien-3-yyli)metoksi]fenyylietyyli]-imidatsolimononitraatin polymorfien B ja C valmistamiseksi

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PCT/ES1995/000001 WO1996020939A1 (es) 1995-01-04 1995-01-04 POLYMORFOS B Y C DE MONONITRATO DE 1-[2,4-DICLORO-β-[(7-CLOROBENZO[b]TIEN-3-IL)METOXI]FENETIL]IMIDAZOL

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ES2249991A1 (es) * 2004-09-13 2006-04-01 Ferrer Internacional, S.A. Procedimiento de fabricacion de compuestos imidazolicos, sus sales y sus pseudopolimorfos.

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US7056321B2 (en) 2000-08-01 2006-06-06 Endius, Incorporated Method of securing vertebrae
ES2203316B1 (es) * 2002-02-11 2005-03-01 Ferrer Internacional, S.A. R-(-)-1-(2-(7-cloro-benzo(b)tiofen-3-il-metoxi)-2-(2,4-dicloro-fenil)-etil)1h-imidazol.
DE10223913A1 (de) * 2002-05-29 2003-12-11 Bayer Cropscience Ag Verfahren zur Herstellung spezifischer Kristallmodifikationen polymorpher Substanzen
ES2249992B1 (es) * 2004-09-13 2007-03-01 Ferrer Internacional, S.A. Un procedimiento para fabricar compuestos enantiomericos del imidazol.
KR100738999B1 (ko) * 2006-06-15 2007-07-25 (주)대우건설 강재 덕트를 이용한 조립구조를 가지는 프리캐스트콘크리트 세그먼트 및 그 연결 조립구조

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Publication number Priority date Publication date Assignee Title
ES2249991A1 (es) * 2004-09-13 2006-04-01 Ferrer Internacional, S.A. Procedimiento de fabricacion de compuestos imidazolicos, sus sales y sus pseudopolimorfos.
ES2249991B1 (es) * 2004-09-13 2007-03-01 Ferrer Internacional, S.A. Procedimiento de fabricacion de compuestos imidazolicos, sus sales y sus pseudopolimorfos.

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NZ278402A (en) 1997-10-24
NO963291D0 (no) 1996-08-07
NO963291L (no) 1996-08-07
DK0748806T3 (da) 1999-04-19
AU691234B2 (en) 1998-05-14
FI963392A0 (fi) 1996-08-30
NO310915B1 (no) 2001-09-17
ES2120720T3 (es) 1998-11-01
CA2184411A1 (en) 1996-07-11
AU1387295A (en) 1996-07-24
US5939555A (en) 1999-08-17
FI111366B (fi) 2003-07-15
EP0748806B1 (en) 1998-07-08
JPH09510234A (ja) 1997-10-14
CA2184411C (en) 2004-05-11
DE69503364T2 (de) 1999-04-15
JP3250809B2 (ja) 2002-01-28
EP0748806A1 (en) 1996-12-18
KR970701187A (ko) 1997-03-17
DE69503364D1 (de) 1998-08-13
KR100336642B1 (ko) 2002-11-23
FI963392L (fi) 1996-08-30

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