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

Info

Publication number
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
Authority
ES
Spain
Prior art keywords
polymorph
oxadiazol
nitrobenzene
pyridin
dichloro
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.)
Active
Application number
ES09722681.5T
Other languages
English (en)
Inventor
David Alexander Learmonth
Keith Lorimer
Kevin Wayne Meyer
Tibor Eszenyi
Álmosné KOVÁCH
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bial Portela and Cia SA
Original Assignee
Bial Portela and Cia SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bial Portela and Cia SA filed Critical Bial Portela and Cia SA
Application granted granted Critical
Publication of ES2565080T3 publication Critical patent/ES2565080T3/es
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Anesthesiology (AREA)
  • Psychology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

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)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
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

Publications (1)

Publication Number Publication Date
ES2565080T3 true ES2565080T3 (es) 2016-03-31

Family

ID=40585552

Family Applications (1)

Application Number Title Priority Date Filing Date
ES09722681.5T Active ES2565080T3 (es) 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

Country Status (16)

Country Link
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)
IL (1) IL207854A0 (es)
MX (1) MX2010009610A (es)
RU (1) RU2010139315A (es)
TW (1) TW200942531A (es)
WO (1) WO2009116882A1 (es)

Families Citing this family (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BRPI0613859B8 (pt) 2005-07-26 2021-05-25 Bial Portela & Ca Sa inibidores da comt, seus usos, e composição farmacêutica
EP1845097A1 (en) 2006-04-10 2007-10-17 Portela & Ca., S.A. Oxadiazole derivatives as COMT inhibitors
EP2124947B1 (en) 2007-01-31 2017-07-19 BIAL - Portela & Ca., S.A. Dosage regimen for comt inhibitors
CA2718772C (en) * 2008-03-17 2017-05-02 David Alexander Learmonth Crystal forms of 5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridine-3-yl)[1,2,4]oxadiazol-5-yl]-3-nit robenzene-1,2-diol
CN102355900A (zh) * 2008-07-29 2012-02-15 比艾尔-坡特拉有限公司 硝基儿茶酚的给药方式
CN102438595B (zh) * 2009-04-01 2016-04-27 巴尔-波特拉及康邦亚股份有限公司 包括硝基儿茶酚衍生物的药物制剂及其制备方法
CN105878242A (zh) * 2009-04-01 2016-08-24 巴尔-波特拉及康邦亚股份有限公司 包括硝基儿茶酚衍生物的药物制剂及其制备方法
US9848134B2 (en) 2010-04-23 2017-12-19 Flir Systems, Inc. Infrared imager with integrated metal layers
US20140045900A1 (en) 2011-02-11 2014-02-13 Bial-Portela & Ca, S.A. Administration regime for nitrocatechols
PT3604299T (pt) * 2011-12-13 2023-10-31 Bial Portela & Ca Sa Composto químico útil como intermediário para a preparação de um inibidor de catecol-o-metiltransferase
WO2016083863A1 (en) 2014-11-28 2016-06-02 Bial - Portela & Ca, S.A. Medicaments for slowing parkinson's disease
HUE047646T2 (hu) * 2015-05-20 2020-05-28 Idorsia Pharmaceuticals Ltd Az (S)-3-{4-[5-(2-ciklopentil-6-metoxi-piridin-4-il)-[1,2,4]oxadiazol-3-il]-2-etil-6-metil-fenoxi} -propán-1,2-diol vegyület kristályformája
RU2659987C2 (ru) * 2016-12-07 2018-07-04 Федеральное государственное бюджетное образовательное учреждение высшего образования "Московский государственный университет имени М.В. Ломоносова" (МГУ) Планарный твердофазный оптический сенсор для определения белковых соединений методом спектроскопии гигантского комбинационного рассеяния и его применение для детектирования белковых соединений
CN115335036A (zh) * 2020-03-13 2022-11-11 巴尔-波特拉及康邦亚股份有限公司 微粉化的奥匹卡朋
GB202011709D0 (en) 2020-07-28 2020-09-09 Bial Portela & Ca Sa Solid dispersion of opicapone
GB202016425D0 (en) 2020-10-16 2020-12-02 Bial Portela & Ca Sa Treatment regimens for parkinson's disease
KR20230118933A (ko) 2020-12-17 2023-08-14 바이알 - 포르텔라 앤드 씨에이 에스에이 초기 특발성 파킨슨병에 대한 치료 요법
GB202219669D0 (en) 2022-12-23 2023-02-08 Bial Portela & Ca Sa Processes and intermediates for synthesising opicapone

Family Cites Families (76)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1532178A (en) 1921-07-25 1925-04-07 Louis A Godbold Lubricator
FR1260080A (fr) 1960-03-22 1961-05-05 Materiel De Forage Soc De Fab Trépan à molettes étanche
US3647809A (en) 1968-04-26 1972-03-07 Chinoin Gyogyszer Es Vegyeszet Certain pyridyl-1 2 4-oxadiazole derivatives
US4022901A (en) 1975-03-05 1977-05-10 E. R. Squibb & Sons, Inc. 3-Pyridinyl-5-isothiocyanophenyl oxadiazoles
US4264573A (en) 1979-05-21 1981-04-28 Rowell Laboratories, Inc. Pharmaceutical formulation for slow release via controlled surface erosion
US4386668A (en) 1980-09-19 1983-06-07 Hughes Tool Company Sealed lubricated and air cooled rock bit bearing
US5236952A (en) 1986-03-11 1993-08-17 Hoffmann-La Roche Inc. Catechol derivatives
DK175069B1 (da) 1986-03-11 2004-05-24 Hoffmann La Roche Pyrocatecholderivater
YU213587A (en) 1986-11-28 1989-06-30 Orion Yhtymae Oy Process for obtaining new pharmacologic active cateholic derivatives
DE3840954A1 (de) 1988-12-05 1990-06-07 Shell Int Research Herstellung von 2-chlornicotinsaeureestern
EP0462639A1 (en) 1990-06-05 1991-12-27 Shell Internationale Researchmaatschappij B.V. Preparation of 2-chloropyridine derivatives
EP0487774B1 (en) 1990-11-29 1994-10-26 Wei Ming Pharmaceutical Mfg. Co. Ltd. A direct tabletting auxiliary
EP0619814A1 (en) 1991-12-31 1994-10-19 Fujisawa Pharmaceutical Co., Ltd. Oxadiazole derivatives having acetylcholinesterase-inhibitory and muscarinic agonist activity
FR2730322B1 (fr) 1995-02-02 1997-04-30 Imago Monture de lunettes metallique
DE19628617A1 (de) 1996-07-16 1998-01-22 Basf Ag Direkttablettierhilfsmittel
US6206110B1 (en) 1996-09-09 2001-03-27 Smith International, Inc. Protected lubricant reservoir with pressure control for sealed bearing earth boring drill bit
JP2002526482A (ja) 1998-09-18 2002-08-20 バーテックス ファーマシューティカルズ インコーポレイテッド ｐ３８のインヒビター
GB2344819A (en) 1998-12-18 2000-06-21 Portela & Ca Sa 2-Phenyl-1-(3,4-dihydroxy-5-nitrophenyl)-1-ethanones
FI109453B (fi) 1999-06-30 2002-08-15 Orion Yhtymae Oyj Farmaseuttinen koostumus
IL131037A (en) 1999-07-22 2004-06-20 Israel Atomic Energy Comm Method for making threedimensional photonic band-gap crystals
BR0013427A (pt) 1999-08-19 2002-07-30 Nps Pharma Inc Compostos heteropolicìclicos e seus usos como antagonistas no receptor de glutamato metabotrópico
US6660753B2 (en) 1999-08-19 2003-12-09 Nps Pharmaceuticals, Inc. Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists
US20020048610A1 (en) * 2000-01-07 2002-04-25 Cima Michael J. High-throughput formation, identification, and analysis of diverse solid-forms
FI20000635A0 (fi) 2000-03-17 2000-03-17 Orion Yhtymae Oyj COMT-inhibiittoreiden käyttö analgeettina
SE0001438D0 (sv) 2000-04-18 2000-04-18 Axon Chemicals Bv New chemical compounds and their use in therapy
DE10029201A1 (de) 2000-06-19 2001-12-20 Basf Ag Verfahren zur Herstellung fester oraler Darreichungsformen mit retardierender Wirkstoffreisetzung
GB2363792A (en) 2000-06-21 2002-01-09 Portela & Ca Sa Nitrocatechols
WO2002017175A1 (fr) 2000-08-24 2002-02-28 Sagawa Express Co., Ltd. Procede de paiement par carte pour facturation de service concernant une distribution ou un transport physiques
CN1166626C (zh) 2000-08-30 2004-09-15 李凌松 三或四取代苯基化合物、其制备方法及应用
US20040097555A1 (en) 2000-12-26 2004-05-20 Shinegori Ohkawa Concomitant drugs
WO2002051442A1 (fr) 2000-12-26 2002-07-04 Takeda Chemical Industries, Ltd. Co-prescriptions
PL369598A1 (en) 2001-02-21 2005-05-02 Nps Pharmaceuticals, Inc. Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists
AU2002310187A1 (en) 2001-05-30 2002-12-09 Lg Biomedical Institute Inhibitors of protein kinase for the treatment of disease
KR20040004705A (ko) 2001-06-08 2004-01-13 시토비아 인크. 카스파제의 활성제 및 아폽토시스의 유도제로서의 치환된3-아릴-5-아릴-[1,2,4]-옥사디아졸과 유사체 및 이의 용도
US6627646B2 (en) * 2001-07-17 2003-09-30 Sepracor Inc. Norastemizole polymorphs
ES2280602T3 (es) 2001-07-26 2007-09-16 Merck Patent Gmbh Uso de 2-(5-(4-fluorofenil)-3-piridilmetilaminometil)-cromano y sus sales fisiologicamente aceptables.
JP4379853B2 (ja) 2001-10-05 2009-12-09 惠民製藥股▲分▼有限公司 直接錠剤化用調合物および補助剤の調合方法
WO2004058253A1 (en) 2002-12-18 2004-07-15 Cytovia, Inc. 3,5-disubstituted-[1,2,4]-oxadiazoles and analogs as activators of caspases and inducers of apoptosis and the use thereof
WO2005006945A2 (en) 2003-07-03 2005-01-27 The Salk Institute For Biological Studies Methods for treating neural disorders and compounds useful therefor
US7226920B2 (en) 2003-08-06 2007-06-05 Vertex Pharmaceuticals Inc. Aminotriazole compounds useful as inhibitors of protein kinases
US7300406B2 (en) 2003-09-30 2007-11-27 Carter Vandette B Medical examination apparatus
GB0325956D0 (en) 2003-11-06 2003-12-10 Addex Pharmaceuticals Sa Novel compounds
ATE464303T1 (de) 2004-04-28 2010-04-15 Vertex Pharma Als inhibitoren von rock und anderen proteinkinasen geeignete zusammensetzungen
GB0510143D0 (en) 2005-05-18 2005-06-22 Addex Pharmaceuticals Sa Novel compounds A1
JP2008519811A (ja) 2004-11-10 2008-06-12 オリオン コーポレーション 下肢静止不能症候群の治療
EP1827453A1 (en) 2004-12-06 2007-09-05 Themis Laboratories Private Limited Sulfonylurea compositions and a process for its preparation
US20080051441A1 (en) 2004-12-28 2008-02-28 Astrazeneca Ab Aryl Sulphonamide Modulators
JP2008525524A (ja) 2004-12-28 2008-07-17 アストラゼネカ・アクチエボラーグ アリールスルホンアミドモジュレーター
AU2006239418A1 (en) 2005-04-26 2006-11-02 Neurosearch A/S Novel oxadiazole derivatives and their medical use
US20060257473A1 (en) 2005-05-11 2006-11-16 Porranee Puranajoti Extended release tablet
GB0510139D0 (en) 2005-05-18 2005-06-22 Addex Pharmaceuticals Sa Novel compounds B1
EP2298734A3 (en) 2005-06-03 2011-07-13 Abbott Laboratories Cyclobutyl amine derivatives
US20090000437A1 (en) 2005-07-14 2009-01-01 Provo Craft And Novelty, Inc. Methods for Cutting
BRPI0613859B8 (pt) 2005-07-26 2021-05-25 Bial Portela & Ca Sa inibidores da comt, seus usos, e composição farmacêutica
FR2889525A1 (fr) 2005-08-04 2007-02-09 Palumed Sa Nouveaux derives de polyquinoleines et leur utilisation therapeutique.
US20070048384A1 (en) 2005-08-26 2007-03-01 Joerg Rosenberg Pharmaceutical compositions
US20090111778A1 (en) 2005-11-18 2009-04-30 Richard Apodaca 2-Keto-Oxazoles as Modulators of Fatty Acid Amide Hydrolase
EP1956013B1 (en) 2005-11-30 2016-04-13 Fujifilm RI Pharma Co., Ltd. Diagnostic and remedy for disease caused by amyloid aggregation and/or deposition
GB0606774D0 (en) 2006-04-03 2006-05-10 Novartis Ag Organic compounds
EP1845097A1 (en) 2006-04-10 2007-10-17 Portela & Ca., S.A. Oxadiazole derivatives as COMT inhibitors
PE20080906A1 (es) 2006-08-17 2008-07-05 Kemia Inc Derivados heteroarilo como inhibidores de citocina
US20080167286A1 (en) 2006-12-12 2008-07-10 Abbott Laboratories Pharmaceutical compositions and their methods of use
US8486979B2 (en) 2006-12-12 2013-07-16 Abbvie Inc. 1,2,4 oxadiazole compounds and methods of use thereof
JP2008162955A (ja) 2006-12-28 2008-07-17 Chugai Pharmaceut Co Ltd バリン含有高密度顆粒剤
EP2124947B1 (en) 2007-01-31 2017-07-19 BIAL - Portela & Ca., S.A. Dosage regimen for comt inhibitors
AR065802A1 (es) 2007-03-22 2009-07-01 Schering Corp Formulaciones de comprimidos que contienen sales de 8- [( 1- ( 3,5- bis- (trifluorometil) fenil) -etoxi ) - metil) -8- fenil -1, 7- diaza- spiro [ 4,5] decan -2- ona y comprimidos elaborados a partir de estas
WO2009029632A1 (en) 2007-08-27 2009-03-05 Helicon Therapeutics, Inc. Therapeutic isoxazole compounds
MX2010009043A (es) * 2008-02-28 2010-10-25 Bial Portela & Ca Sa Composicion farmaceutica para farmacos poco solubles.
CA2718772C (en) * 2008-03-17 2017-05-02 David Alexander Learmonth Crystal forms of 5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridine-3-yl)[1,2,4]oxadiazol-5-yl]-3-nit robenzene-1,2-diol
CN102355900A (zh) 2008-07-29 2012-02-15 比艾尔-坡特拉有限公司 硝基儿茶酚的给药方式
US8827197B2 (en) 2008-11-04 2014-09-09 Microgreen Polymers Inc Apparatus and method for interleaving polymeric roll for gas impregnation and solid-state foam processing
CN102438595B (zh) 2009-04-01 2016-04-27 巴尔-波特拉及康邦亚股份有限公司 包括硝基儿茶酚衍生物的药物制剂及其制备方法
CN105878242A (zh) 2009-04-01 2016-08-24 巴尔-波特拉及康邦亚股份有限公司 包括硝基儿茶酚衍生物的药物制剂及其制备方法
EA026419B1 (ru) 2010-03-04 2017-04-28 Орион Корпорейшн Применение леводопы, карбидопы и энтакапона для лечения болезни паркинсона
US20140045900A1 (en) 2011-02-11 2014-02-13 Bial-Portela & Ca, S.A. Administration regime for nitrocatechols
PT3604299T (pt) 2011-12-13 2023-10-31 Bial Portela & Ca Sa Composto químico útil como intermediário para a preparação de um inibidor de catecol-o-metiltransferase

Also Published As

Publication number Publication date
AR070907A1 (es) 2010-05-12
RU2010139315A (ru) 2012-04-27
EP2276758A1 (en) 2011-01-26
JP2015044837A (ja) 2015-03-12
TW200942531A (en) 2009-10-16
JP2011514380A (ja) 2011-05-06
IL207854A0 (en) 2010-12-30
US8975410B2 (en) 2015-03-10
CA2718772A1 (en) 2009-09-24
US9845316B2 (en) 2017-12-19
CA2718772C (en) 2017-05-02
US20110112301A1 (en) 2011-05-12
AU2009226221A1 (en) 2009-09-24
KR20110002462A (ko) 2011-01-07
CN102015696A (zh) 2011-04-13
EP2276758B1 (en) 2016-01-06
BRPI0908731A2 (pt) 2017-05-16
WO2009116882A1 (en) 2009-09-24
MX2010009610A (es) 2010-09-30
US20150166519A1 (en) 2015-06-18
CL2009000628A1 (es) 2010-04-09

Similar Documents

Publication Publication Date Title
ES2565080T3 (es) 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
JP6924839B2 (ja) 置換された多環性ピリドン誘導体の立体選択的な製造方法
TWI408135B (zh) 腎外髓質鉀通道抑制劑
AR107173A2 (es) Formas polimórficas e hidrato y sales de 6-{difluor[6-(1-metil-1h-pirazol-4-il)[1,2,4]triazolo[4,3-b]piridazin-3-il]metil}quinolina
ES2618939T3 (es) Sal de camsilato
PE20140002A1 (es) Proceso de elaboracion para derivados de pirimidina
CO6120149A1 (es) Nueva forma cristalina vi de la agomelatina su procedimiento de preparacion y las composiciones farmaceuticas que la contienen
Hung et al. Novel synthesis of 5-methyl-5, 10-dihydroindolo [3, 2-b] indoles by Pd-catalyzed C–C and two-fold C–N coupling reactions
WO2011123947A8 (en) Synthesis of chiral 2-(1h-indazol-6-yl)-spiro[cyclopropane-1,3'- indolin]-2'-ones
RU2016146119A (ru) Новый кристалл тетрациклического соединения
AU2019345053A1 (en) Inhibiting ubiquitin specific peptidase 9X
AR075418A1 (es) Polimorfo cristalino de 3-{[5-(azetidin-1-ilcarbonil)pirazin-2-il]oxi}-5-{[(1s)-1-metil-2-(metiloxi)etil]oxi}-n-(5-metilpirazin-2-il)benzamida,composiciones farmaceuticas que los contienen, proceso para prepararla y uso de las mismas para el tratamiento de la diabetes tipo ii y/u obesidad.
RU2009141831A (ru) Лечение мышечной дистрофии дюшенна
RU2011143166A (ru) Новые кристаллические формы адефовира дипивоксила и способы его получения
WO2013124748A4 (en) Novel polymorphs of azilsartan medoxomil potassium
US9708310B2 (en) Phenanthroindolizidine and phenanthroquinolizidine alkaloid having a hydroxyl group on the phenanthrene ring thereof, preparation method and use thereof
AR103209A1 (es) Formas polimorficas del 4-metilbencil(3s,4r)-3-fluoro-4-[(pirimidin-2-ilamino)metil]piperidina-1-carboxilato
Ibrahim et al. Sequential staudinger ketene–imine cycloaddition, RCM approach to polycyclic macrocyclic bisazetidinones
Lee et al. Ailanthoidol derivatives and their anti-inflammatory effects
Choi et al. Synthesis of 2-(4-hydroxyphenyl) benzofurans and their application to β-amyloid aggregation inhibitor
PE20231071A1 (es) Formas cristalinas de (9r,13s)-13-{4-[5-cloro-2-(4-cloro-1h-1,2,3-triazol-1- il)fenil]-6-oxo-1,6-dihidropirimidin-1-il}-3-(difluorometil)-9-metil-3,4,7,15- tetraazatriciclo[12.3.1.02,6]octadeca-1(18),2(6),4,14,16-pentaen-8-ona
RU2017145927A (ru) Кристаллический лиганд 6,6'-[[3,3',5,5'-тетракис(1,1-диметилэтил)-[1,1'-бифенил]-2,2'-диил]бис(окси)]бисдибензо[d,f][1,3,2]-диоксафосфепин
Yang et al. Structure of the condensed product of aromatic o-aminonitrile with carbonyl compound and its mechanism
Shumilova et al. Synthesis of sulfonate derivatives of 4-heteryl-isoxazoles
Vincze et al. Simple route to multisubstituted tetrahydropyrimidines