ES2565080T3 - Formas cristalinas de 5-[3-(2,5-dicloro-4,6-dimetil-1-oxi-piridin-3-il)-[1,2,4]oxadiazol-5-il]-3-nitrobenceno-1,2-diol - Google Patents

Formas cristalinas de 5-[3-(2,5-dicloro-4,6-dimetil-1-oxi-piridin-3-il)-[1,2,4]oxadiazol-5-il]-3-nitrobenceno-1,2-diol Download PDF

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ES2565080T3
ES2565080T3 ES09722681.5T ES09722681T ES2565080T3 ES 2565080 T3 ES2565080 T3 ES 2565080T3 ES 09722681 T ES09722681 T ES 09722681T ES 2565080 T3 ES2565080 T3 ES 2565080T3
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polymorph
oxadiazol
nitrobenzene
pyridin
dichloro
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David Alexander Learmonth
Keith Lorimer
Kevin Wayne Meyer
Tibor Eszenyi
Álmosné KOVÁCH
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Bial Portela and Cia SA
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/20—Hypnotics; Sedatives
    • 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
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/10—Antioedematous agents; Diuretics
    • 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
    • A61P9/12—Antihypertensives
    • 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

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Abstract

Polimorfo de 5-[3-(2,5-dicloro-4,6-dimetil-1-oxi-piridin-3-il)-[1,2,4]oxadiazol-5-il]-3-nitrobenceno-1,2-diol, caracterizado por que su difractograma de rayos-X de polvo presenta los siguientes ángulos 2θ: 5,7, 6,9, 13,8 y 19,6.

Description

imagen1
imagen2
imagen3
imagen4
imagen5
preferiblemente, el polimorfo B se caracteriza por 2 a 10, preferiblemente 3 a 5, picos en el intervalo de aproximadamente 5 a aproximadamente 25 °/2θ. Incluso más preferiblemente, el polimorfo B se caracteriza por las señales a 5,7, 6,9, 11,9, 13,8, 16,9 y 19,6 °/2θ. Lo más preferiblemente, el polimorfo B se caracteriza por las señales a 5,7, 6,9, 13,8 y 19,6 °/2θ.
5 Además, el polimorfo B se puede caracterizar también por tener un pico exotérmico a 237ºC en un termograma de calorimetría diferencial de barrido (DSC). Tales análisis pueden indicar también un pico hombro a 231ºC.
Además, el polimorfo B es preferiblemente una forma anhidra como se demuestra por una falta de desorción de disolvente en experimentos combinados de calorimetría diferencial de barrido (DSC) y análisis termogravimétrico (TGA) antes de la descomposición energética. Sin embargo, el empaquetamiento molecular del polimorfo B permite
10 la acomodación de agua cristalina sin alterar sustancialmente la red cristalina.
El polimorfo B se caracteriza también por una o más de las siguientes posiciones de pico FT-Raman:
tabla 5 – Espectros Raman de polimorfo B
Posición de pico (cm-1)
Intensidad relativa (%)
141
26
214
23
235
16
253
20
280
14
339
25
361
18
372
19
399
15
415
18
440
12
463
15
505
49
526
21
710
14
812
54
887
11
926
13
970
12
1001
22
1059
19
1157
10
1227
14
1292
49
1317
43
1385
50
1406
34
1444
32
7
imagen6
imagen7
imagen8
Posición de pico (cm-1)
Intensidad relativa (%)
1585
100
1630
59
2918
15
Preferiblemente, el polimorfo C se caracteriza por una o más, preferiblemente 2 a 6, y más preferiblemente 3 a 5, posiciones de pico de la tabla anterior. Más preferiblemente, el polimorfo C se caracteriza por uno o más de los picos a 143, 507, 810, 1244, 1281, 1317, 1352, 1387, 1406, 1537, 1585, y 1630 cm-1. Lo más preferiblemente, el polimorfo C se caracteriza por los picos a 1387, 1406, 1537, 1585, y 1630 cm-1 .
El polimorfo C también se caracteriza por una o más de las siguientes posiciones de pico en 13C-RMN de estado sólido:
tabla 9 – 13C-RMN de estado sólido de polimorfo C
Posiciones de pico (ppm)
173,9
165,0
150,7
141,0
138,6
133,5
122,8
120,3
114,0
112,4
41,1
20,2
17,9
10 Preferiblemente, el polimorfo C se caracteriza por una o más, preferiblemente 2 a 6, y más preferiblemente 3 a 5, posiciones de pico de la tabla anterior. Lo más preferiblemente, el polimorfo C se caracteriza por los picos a 150,7, 133,5, 114,0 y 20,2 ppm.
Se describe también un polimorfo de 5-[3-(2,5-dicloro-4,6-dimetil-1-oxi-piridin-3-il)-[1,2,4]oxadiazol-5-il]-3nitrobenceno-1,2-diol denominado polimorfo D. En la sección experimental se da un procedimiento para la
15 preparación de polimorfo D.
El polimorfo D es un polimorfo cristalino y, por tanto, se caracteriza por uno o más de los picos de su patrón de difracción de rayos-X de polvo (XRPD). El patrón de difracción se registró con radiación de Cu-Kα y se da en la tabla siguiente.
20 tabla 10 -XRPD de polimorfo D
Posición de pico (°2θ)
Intensidad relativa (%)
11,6
21
12,3
23
20,0
43
11
Posición de pico (°2θ)
Intensidad relativa (%)
20,7
100
21,4
69
23,8
25
24,8
26
26,6
11
27,4
12
28,0
12
29,1
31
31,1
56
32,0
20
33,3
39
35,0
23
36,0
35
Preferiblemente, el polimorfo D se caracteriza por uno o más de los picos anteriores en el intervalo de aproximadamente 5 a aproximadamente 25 °/2θ, que es una región muy característica de los XRPDs. Más preferiblemente, el polimorfo D se caracteriza por 2 a 10, preferiblemente 3 a 5, picos en el intervalo de
5 aproximadamente 5 a aproximadamente 25 °/2θ. Incluso más preferiblemente, el polimorfo D se caracteriza por las señales a 11,6, 12,3, 20,0, 20,7, 21,4 y 24,8 °/2θ. Lo más preferiblemente, el polimorfo D se caracteriza por las señales a 12,3, 20,0, 20,7 y 21,4 °/2θ.
Se describe también un polimorfo de 5-[3-(2,5-dicloro-4,6-dimetil-1-oxi-piridin-3-il)-[1,2,4]oxadiazol-5-il]-3nitrobenceno-1,2-diol denominado polimorfo E. En la sección experimental se da un procedimiento para la
10 preparación de polimorfo E.
El polimorfo E es un polimorfo cristalino y, por tanto, se caracteriza por uno o más de los picos de su patrón de difracción de rayos-X de polvo (XRPD). El patrón de difracción se registró con radiación de Cu-Kα y se da en la tabla siguiente.
15 tabla 11 -XRPD de polimorfo E
Posición de pico (°2θ)
Intensidad relativa (%)
4,5
8
5,4
34
6,2
36
6,9
4
7,8
52
8,4
3
9,8
100
10,8
89
11,2
69
11,5
11
12,2
87
12,4
31
12
imagen9
imagen10
imagen11
imagen12
imagen13
imagen14
imagen15
imagen16

Claims (1)

  1. imagen1
ES09722681.5T 2008-03-17 2009-03-16 Formas cristalinas de 5-[3-(2,5-dicloro-4,6-dimetil-1-oxi-piridin-3-il)-[1,2,4]oxadiazol-5-il]-3-nitrobenceno-1,2-diol Active ES2565080T3 (es)

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US6972108P 2008-03-17 2008-03-17
US69721P 2008-03-17
PCT/PT2009/000013 WO2009116882A1 (en) 2008-03-17 2009-03-16 Crystal forms of 5- [3- (2, 5-dichloro-4, 6-dimethyl-1-oxy-pyridine-3-yl) [1,2,3] oxadiazol-5-yl] -3-nit robenzene-1, 2-diol

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ES2565080T3 true ES2565080T3 (es) 2016-03-31

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US (2) US8975410B2 (es)
EP (1) EP2276758B1 (es)
JP (2) JP2011514380A (es)
KR (1) KR20110002462A (es)
CN (1) CN102015696A (es)
AR (1) AR070907A1 (es)
AU (1) AU2009226221A1 (es)
BR (1) BRPI0908731A2 (es)
CA (1) CA2718772C (es)
CL (1) CL2009000628A1 (es)
ES (1) ES2565080T3 (es)
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MX (1) MX2010009610A (es)
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WO (1) WO2009116882A1 (es)

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