NO332143B1 - Imidazolderivater, fremgangsmate for fremstilling av slike, medikament inneholdende slike, slike forbindelser for anvendelse til behandling av sykdom samt anvendelse av slike for fremstilling av medikamenter for behandling av sykdom - Google Patents

Imidazolderivater, fremgangsmate for fremstilling av slike, medikament inneholdende slike, slike forbindelser for anvendelse til behandling av sykdom samt anvendelse av slike for fremstilling av medikamenter for behandling av sykdom Download PDF

Info

Publication number: NO332143B1
Authority: NO; Norway
Prior art keywords: formula; methyl; compound; chloro; ylethynyl
Prior art date: 2003-06-05

Application number

NO20055465A

Other languages

English (en)

Norwegian (no)

Other versions

NO20055465L (no

Inventor

Sabine Kolczewski

Bernd Buettelmann

Georg Jaeschke

Eric Vieira

Simona Maria Ceccarelli

Richard Hugh Phillip Porter

Original Assignee

Hoffmann La Roche

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.)

2003-06-05

Filing date

2005-11-18

Publication date

2012-07-02

2005-11-18 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2005-11-18 Publication of NO20055465L publication Critical patent/NO20055465L/no

2012-07-02 Publication of NO332143B1 publication Critical patent/NO332143B1/no

Links

239000003814 drug Substances 0.000 title claims abstract description 12
229940079593 drug Drugs 0.000 title claims abstract description 9
150000001875 compounds Chemical class 0.000 title claims description 173
238000000034 method Methods 0.000 title claims description 27
238000002360 preparation method Methods 0.000 title claims description 11
230000008569 process Effects 0.000 title claims description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title abstract description 7
150000002460 imidazoles Chemical class 0.000 title abstract description 4
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title abstract description 4
201000010099 disease Diseases 0.000 title description 3
230000001684 chronic effect Effects 0.000 claims abstract description 14
230000001154 acute effect Effects 0.000 claims abstract description 10
208000012902 Nervous system disease Diseases 0.000 claims abstract description 8
208000025966 Neurological disease Diseases 0.000 claims abstract description 8
230000002265 prevention Effects 0.000 claims abstract description 8
150000003839 salts Chemical class 0.000 claims description 28
229910052736 halogen Inorganic materials 0.000 claims description 27
150000002367 halogens Chemical class 0.000 claims description 27
208000002193 Pain Diseases 0.000 claims description 17
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 15
208000019901 Anxiety disease Diseases 0.000 claims description 9
230000036506 anxiety Effects 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 8
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
208000000094 Chronic Pain Diseases 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
239000011737 fluorine Substances 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000003373 pyrazinyl group Chemical group 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
208000005298 acute pain Diseases 0.000 claims description 6
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
HVPDVQJRUVMRKM-UHFFFAOYSA-N 2-chloro-4-[2-[1-(4-fluorophenyl)-2-methylimidazol-4-yl]ethynyl]pyridine Chemical compound CC1=NC(C#CC=2C=C(Cl)N=CC=2)=CN1C1=CC=C(F)C=C1 HVPDVQJRUVMRKM-UHFFFAOYSA-N 0.000 claims description 4
206010046543 Urinary incontinence Diseases 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
WAQFQJHGDDKMQZ-UHFFFAOYSA-N 2-[4-[2-(2-chloropyridin-4-yl)ethynyl]-2-methylimidazol-1-yl]-4-(trifluoromethyl)pyrimidine Chemical compound CC1=NC(C#CC=2C=C(Cl)N=CC=2)=CN1C1=NC=CC(C(F)(F)F)=N1 WAQFQJHGDDKMQZ-UHFFFAOYSA-N 0.000 claims description 3
VNTBEOOUSIHCDG-UHFFFAOYSA-N 2-[4-[2-(2-chloropyridin-4-yl)ethynyl]-2-methylimidazol-1-yl]pyrazine Chemical compound CC1=NC(C#CC=2C=C(Cl)N=CC=2)=CN1C1=CN=CC=N1 VNTBEOOUSIHCDG-UHFFFAOYSA-N 0.000 claims description 3
SUXATGYKFSJNDF-UHFFFAOYSA-N 2-chloro-4-[2-[1-(3,5-difluorophenyl)-2-methylimidazol-4-yl]ethynyl]pyridine Chemical compound CC1=NC(C#CC=2C=C(Cl)N=CC=2)=CN1C1=CC(F)=CC(F)=C1 SUXATGYKFSJNDF-UHFFFAOYSA-N 0.000 claims description 3
URCAGOXDMQYRHD-UHFFFAOYSA-N 2-chloro-4-[2-[2-methyl-1-[6-(trifluoromethyl)pyridin-2-yl]imidazol-4-yl]ethynyl]pyridine Chemical compound CC1=NC(C#CC=2C=C(Cl)N=CC=2)=CN1C1=CC=CC(C(F)(F)F)=N1 URCAGOXDMQYRHD-UHFFFAOYSA-N 0.000 claims description 3
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239000000654 additive Substances 0.000 claims description 3
UPZWINBEAHDTLA-UHFFFAOYSA-N basimglurant Chemical compound CC=1N(C=2C=CC(F)=CC=2)C(C)=NC=1C#CC1=CC=NC(Cl)=C1 UPZWINBEAHDTLA-UHFFFAOYSA-N 0.000 claims description 3
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125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 claims description 2
DDDPMHSOPQMYHR-UHFFFAOYSA-N 2-chloro-4-[2-[1-(3,5-difluorophenyl)-2,5-dimethylimidazol-4-yl]ethynyl]pyridine Chemical compound CC=1N(C=2C=C(F)C=C(F)C=2)C(C)=NC=1C#CC1=CC=NC(Cl)=C1 DDDPMHSOPQMYHR-UHFFFAOYSA-N 0.000 claims description 2
SEULXXCCZBUNKA-UHFFFAOYSA-N 2-chloro-4-[2-[1-(5-fluoropyridin-3-yl)-2-methylimidazol-4-yl]ethynyl]pyridine Chemical compound CC1=NC(C#CC=2C=C(Cl)N=CC=2)=CN1C1=CN=CC(F)=C1 SEULXXCCZBUNKA-UHFFFAOYSA-N 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
230000006806 disease prevention Effects 0.000 claims 1
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239000011541 reaction mixture Substances 0.000 description 45
238000007429 general method Methods 0.000 description 37
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239000000243 solution Substances 0.000 description 34
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
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239000002904 solvent Substances 0.000 description 20
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
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239000007787 solid Substances 0.000 description 13
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Classifications

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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- C—CHEMISTRY; METALLURGY
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings

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Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Neurosurgery (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Pain & Pain Management (AREA)
Psychiatry (AREA)
Addiction (AREA)
Psychology (AREA)
Hospice & Palliative Care (AREA)
Anesthesiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

NO20055465A 2003-06-05 2005-11-18 Imidazolderivater, fremgangsmate for fremstilling av slike, medikament inneholdende slike, slike forbindelser for anvendelse til behandling av sykdom samt anvendelse av slike for fremstilling av medikamenter for behandling av sykdom NO332143B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP03012200		2003-06-05
PCT/EP2004/005881 WO2004108701A1 (en)	2003-06-05	2004-06-01	Imidazole derivatives as glutmate receptor antagonists

Publications (2)

Publication Number	Publication Date
NO20055465L NO20055465L (no)	2005-11-18
NO332143B1 true NO332143B1 (no)	2012-07-02

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Application Number	Title	Priority Date	Filing Date
NO20055465A NO332143B1 (no)	2003-06-05	2005-11-18	Imidazolderivater, fremgangsmate for fremstilling av slike, medikament inneholdende slike, slike forbindelser for anvendelse til behandling av sykdom samt anvendelse av slike for fremstilling av medikamenter for behandling av sykdom

Country Status (38)

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US (3)	US7332510B2 (de)
EP (1)	EP1636206B1 (de)
JP (1)	JP4401384B2 (de)
KR (1)	KR100778948B1 (de)
CN (1)	CN100408572C (de)
AR (1)	AR044478A1 (de)
AT (1)	ATE377008T1 (de)
AU (1)	AU2004245208B2 (de)
BR (1)	BRPI0411095B8 (de)
CA (1)	CA2527315C (de)
CL (1)	CL2004001347A1 (de)
CR (1)	CR8094A (de)
CY (1)	CY1107856T1 (de)
DE (1)	DE602004009796T2 (de)
DK (1)	DK1636206T3 (de)
EA (1)	EA010577B1 (de)
EC (1)	ECSP056202A (de)
ES (1)	ES2294504T3 (de)
GT (1)	GT200400117A (de)
HN (1)	HN2004000208A (de)
HR (1)	HRP20070529T3 (de)
IL (1)	IL171930A (de)
MA (1)	MA27881A1 (de)
MX (1)	MXPA05013149A (de)
MY (2)	MY137272A (de)
NO (1)	NO332143B1 (de)
NZ (1)	NZ543637A (de)
PA (1)	PA8604101A1 (de)
PE (1)	PE20050162A1 (de)
PL (1)	PL1636206T3 (de)
PT (1)	PT1636206E (de)
RS (1)	RS53183B (de)
SI (1)	SI1636206T1 (de)
TN (2)	TNSN05309A1 (de)
TW (1)	TWI338007B (de)
UA (1)	UA80888C2 (de)
WO (1)	WO2004108701A1 (de)
ZA (2)	ZA200509807B (de)

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UA80888C2 (en) *	2003-06-05	2007-11-12	Hoffmann La Roche	Imidazole derivatives as glutmate receptor antagonists
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KR101057032B1 (ko) *	2004-06-01	2011-08-16	에프. 호프만-라 로슈 아게	Ｍｇｌｕ5 수용체 길항제로서 피리딘-4-일-에틴일-이미다졸및 피라졸
GB0514296D0 (en) *	2005-07-12	2005-08-17	Novartis Ag	Organic compounds
DE102006011574A1 (de) *	2006-03-10	2007-10-31	Grünenthal GmbH	Substituierte Imidazo[2,1-b]thiazol-Verbindungen und ihre Verwendung zur Herstellung von Arzneimitteln
JP5405311B2 (ja) *	2006-12-21	2014-02-05	エフ．ホフマン−ラロシュアーゲー	ｍＧｌｕＲ５受容体アンタゴニストの多形
US8334287B2 (en) *	2009-07-17	2012-12-18	Hoffmann-La Roche Inc.	Imidazoles
US20120039999A1 (en)	2010-08-11	2012-02-16	Ashish Chatterji	Pharmaceutical compositions of metabotropic glutamate 5 receptor (mglu5) antagonists
US20120040008A1 (en) *	2010-08-11	2012-02-16	Ashish Chatterji	Pharmaceutical compositions of metabotropic glutamate 5 receptor (mglu5) antagonists
MX2013010698A (es)	2011-03-18	2014-02-17	Novartis Ag	Combinaciones de activadores del receptor de acetil-colina nicotinico alfa-7 y antagonistas del receptor de glutamato metabotropico 5 (mglur5) para usarse en la discinesia inducida por dopamina en la enfermedad de parkinson.
CN104603110B (zh) *	2012-10-18	2016-08-31	霍夫曼-拉罗奇有限公司	作为mGluR5受体活性的调节剂的乙炔基衍生物
SG11201501392TA (en) *	2012-10-18	2015-05-28	Hoffmann La Roche	Ethynyl derivatives as modulators of mglur5 receptor activity
BR112018069868A2 (pt) *	2016-03-30	2019-01-29	Sinntaxis AB	modulador alostérico negativo do receptor metabotrópico de glutamato 5, usos de um nam, e método de tratamento ou atenuação de dano cerebral maduro
EP4069685A1 (de) *	2019-12-02	2022-10-12	F. Hoffmann-La Roche AG	Alkynyl-(heteroaryl) -carboxamid-hcn-inhibitoren
IL322310A (en)	2020-06-05	2025-09-01	Noema Pharma Ag	Methods for treating multiple sclerosis complex
MX2023001288A (es) *	2020-07-30	2023-04-28	Noema Pharma Ag	Metodos de tratamiento de la neuralgia del trigemino.
IL322318A (en)	2023-02-02	2025-09-01	Noema Pharma Ag	Methods for treating Dravet syndrome

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US4508560A (en) *	1981-11-11	1985-04-02	Ciba Geigy Corporation	Certain pyridylacetylene compounds, compositions containing same and herbicidal methods of use
TW544448B (en) *	1997-07-11	2003-08-01	Novartis Ag	Pyridine derivatives
JP4815083B2 (ja) *	1999-08-31	2011-11-16	メルク・シャープ・エンド・ドーム・コーポレイション	複素環化合物およびそれの使用方法
JP5154728B2 (ja) *	2000-07-24	2013-02-27	クレニツキー・ファーマシューティカルズ，インコーポレイテッド	神経栄養活性を有する置換５−アルキニルピリミジン
ATE288898T1 (de) *	2000-12-04	2005-02-15	Hoffmann La Roche	Phenylethenyl- oder phenylethinylderivate als glutamatrezeptorantagonisten
EP1458385A4 (de) *	2001-12-19	2005-12-21	Merck & Co Inc	Heteroaryl-substituierte imidazol-modulatoren des metabotropen glutamat-rezeptors-5
EP1556142A4 (de) *	2002-10-24	2006-11-08	Merck & Co Inc	Alkyn-derivate als tracer für die metabotrope glutamat-rezeptor-bindung
TWI292318B (en) *	2003-03-10	2008-01-11	Hoffmann La Roche	Imidazol-4-yl-ethynyl-pyridine derivatives
UA80888C2 (en) *	2003-06-05	2007-11-12	Hoffmann La Roche	Imidazole derivatives as glutmate receptor antagonists
US7091222B2 (en) *	2003-07-03	2006-08-15	Hoffmann-La Roche Inc.	Imidazole derivatives

2004
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- 2004-06-01 EA EA200501887A patent/EA010577B1/ru not_active IP Right Cessation
- 2004-06-01 AT AT04739484T patent/ATE377008T1/de active
- 2004-06-01 PL PL04739484T patent/PL1636206T3/pl unknown
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- 2004-06-01 BR BRPI0411095A patent/BRPI0411095B8/pt not_active IP Right Cessation
- 2004-06-01 ES ES04739484T patent/ES2294504T3/es not_active Expired - Lifetime
- 2004-06-01 MX MXPA05013149A patent/MXPA05013149A/es active IP Right Grant
- 2004-06-01 NZ NZ543637A patent/NZ543637A/en not_active IP Right Cessation
- 2004-06-01 DK DK04739484T patent/DK1636206T3/da active
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- 2004-06-01 AU AU2004245208A patent/AU2004245208B2/en not_active Expired
- 2004-06-01 KR KR1020057023137A patent/KR100778948B1/ko not_active Expired - Lifetime
- 2004-06-01 JP JP2006508238A patent/JP4401384B2/ja not_active Expired - Lifetime
- 2004-06-01 CN CNB2004800156669A patent/CN100408572C/zh not_active Expired - Lifetime
- 2004-06-01 CA CA2527315A patent/CA2527315C/en not_active Expired - Lifetime
- 2004-06-01 RS YU20050892A patent/RS53183B/sr unknown
- 2004-06-01 DE DE602004009796T patent/DE602004009796T2/de not_active Expired - Lifetime
- 2004-06-01 PT PT04739484T patent/PT1636206E/pt unknown
- 2004-06-01 WO PCT/EP2004/005881 patent/WO2004108701A1/en not_active Ceased
- 2004-06-02 US US10/858,969 patent/US7332510B2/en not_active Expired - Lifetime
- 2004-06-02 CL CL200401347A patent/CL2004001347A1/es unknown
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- 2004-06-02 TW TW093115811A patent/TWI338007B/zh not_active IP Right Cessation
- 2004-06-02 PE PE2004000558A patent/PE20050162A1/es active IP Right Grant
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- 2004-06-03 MY MYPI20042150A patent/MY137272A/en unknown
- 2004-06-03 AR ARP040101908A patent/AR044478A1/es active IP Right Grant
2005
- 2005-05-27 MY MYPI20052424A patent/MY143353A/en unknown
- 2005-11-13 IL IL171930A patent/IL171930A/en active IP Right Grant
- 2005-11-14 CR CR8094A patent/CR8094A/es unknown
- 2005-11-18 NO NO20055465A patent/NO332143B1/no unknown
- 2005-12-01 TN TNP2005000309A patent/TNSN05309A1/fr unknown
- 2005-12-02 EC EC2005006202A patent/ECSP056202A/es unknown
- 2005-12-02 ZA ZA200509807A patent/ZA200509807B/en unknown
- 2005-12-09 MA MA28648A patent/MA27881A1/fr unknown
2006
- 2006-11-21 ZA ZA200609681A patent/ZA200609681B/xx unknown
- 2006-11-27 TN TNP2006000391A patent/TNSN06391A1/fr unknown
2007
- 2007-10-31 US US11/930,258 patent/US8481548B2/en active Active
- 2007-12-13 US US11/955,421 patent/US7973165B2/en not_active Expired - Lifetime
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Also Published As

Publication number	Publication date
BRPI0411095B1 (pt)	2018-04-03
IL171930A (en)	2010-12-30
JP2006526588A (ja)	2006-11-24
ES2294504T3 (es)	2008-04-01
DE602004009796D1 (de)	2007-12-13
TWI338007B (en)	2011-03-01
MXPA05013149A (es)	2006-03-17
PT1636206E (pt)	2008-01-28
SI1636206T1 (sl)	2008-02-29
GT200400117A (es)	2005-02-07
CN1802367A (zh)	2006-07-12
CY1107856T1 (el)	2013-06-19
EA200501887A1 (ru)	2006-10-27
CL2004001347A1 (es)	2005-05-06
NZ543637A (en)	2008-04-30
ZA200509807B (en)	2006-12-27
EP1636206A1 (de)	2006-03-22
TNSN05309A1 (fr)	2007-07-10
UA80888C2 (en)	2007-11-12
CA2527315C (en)	2010-08-10
HRP20070529T3 (hr)	2008-05-31
NO20055465L (no)	2005-11-18
TNSN06391A1 (fr)	2008-02-22
US7332510B2 (en)	2008-02-19
BRPI0411095B8 (pt)	2021-05-25
RS20050892A (sr)	2007-12-31
ECSP056202A (es)	2006-04-19
PE20050162A1 (es)	2005-03-22
HN2004000208A (es)	2009-02-03
AU2004245208B2 (en)	2007-04-26
DK1636206T3 (da)	2008-02-11
RS53183B (sr)	2014-06-30
MY137272A (en)	2009-01-30
HK1093070A1 (zh)	2007-02-23
ATE377008T1 (de)	2007-11-15
EA010577B1 (ru)	2008-10-30
WO2004108701A1 (en)	2004-12-16
AR044478A1 (es)	2005-09-14
US7973165B2 (en)	2011-07-05
US20080119489A1 (en)	2008-05-22
EP1636206B1 (de)	2007-10-31
KR100778948B1 (ko)	2007-11-28
CN100408572C (zh)	2008-08-06
ZA200609681B (en)	2008-06-25
US8481548B2 (en)	2013-07-09
DE602004009796T2 (de)	2008-08-28
BRPI0411095A (pt)	2006-07-18
TW200509920A (en)	2005-03-16
AU2004245208A1 (en)	2004-12-16
MA27881A1 (fr)	2006-05-02
KR20060057537A (ko)	2006-05-26
US20080103306A1 (en)	2008-05-01
PL1636206T3 (pl)	2008-04-30
CA2527315A1 (en)	2004-12-16
MY143353A (en)	2011-04-29
JP4401384B2 (ja)	2010-01-20
US20040248888A1 (en)	2004-12-09
IL171930A0 (en)	2006-04-10
PA8604101A1 (es)	2004-12-16
CR8094A (es)	2006-05-30

Publication	Publication Date	Title
EP1606277B1 (de)	2008-05-14	Imidazol-4-yl-ethynyl-pyridin-derivate
US8481548B2 (en)	2013-07-09	Imidazole derivatives
CA2537826C (en)	2012-04-17	Imidazole derivatives
NO332175B1 (no)	2012-07-16	Heteroarylsubstituerte imidazolderivater, fremstilling av slike forbindelser, medikament inneholdende slike forbindelser, slike forbindelser for anvendelse til behandling av sykdom samt anvendelse av slike forbindelser for fremstilling av medikamenter for behandling av sykdom
CA2531210C (en)	2012-05-29	Imidazole derivatives and their use in the treatment of mglur5 receptor mediated disorders
HK1093070B (en)	2009-01-23	Imidazole derivatives as glutamate receptor antagonists