DE60023318T2 - Heteropolycyclische verbindungen und ihre verwendung als antagonisten von metabotropen glutamatrezeptoren - Google Patents
Heteropolycyclische verbindungen und ihre verwendung als antagonisten von metabotropen glutamatrezeptoren Download PDFInfo
- Publication number
- DE60023318T2 DE60023318T2 DE60023318T DE60023318T DE60023318T2 DE 60023318 T2 DE60023318 T2 DE 60023318T2 DE 60023318 T DE60023318 T DE 60023318T DE 60023318 T DE60023318 T DE 60023318T DE 60023318 T2 DE60023318 T2 DE 60023318T2
- Authority
- DE
- Germany
- Prior art keywords
- pyridyl
- oxazole
- oxadiazole
- cyanophenyl
- chloro
- 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.)
- Expired - Lifetime
Links
- 102000016193 Metabotropic glutamate receptors Human genes 0.000 title claims abstract description 53
- 108010010914 Metabotropic glutamate receptors Proteins 0.000 title claims abstract description 53
- 150000001875 compounds Chemical class 0.000 title claims abstract description 52
- 239000005557 antagonist Substances 0.000 title abstract description 19
- 208000012902 Nervous system disease Diseases 0.000 claims abstract description 12
- 208000025966 Neurological disease Diseases 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 23
- CQXOVXIKDZNZMV-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound ClC1=CC=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 CQXOVXIKDZNZMV-UHFFFAOYSA-N 0.000 claims description 20
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 20
- 201000010099 disease Diseases 0.000 claims description 12
- NGKWCJCCZGCLID-UHFFFAOYSA-N 5-(2-chlorophenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound ClC1=CC=CC=C1C1=NC(C=2N=CC=CC=2)=NO1 NGKWCJCCZGCLID-UHFFFAOYSA-N 0.000 claims description 11
- FPYLVHWPDOYNOI-UHFFFAOYSA-N 4-pyridin-2-yl-2-(2,3,6-trifluorophenyl)-1,3-oxazole Chemical compound FC1=CC=C(F)C(C=2OC=C(N=2)C=2N=CC=CC=2)=C1F FPYLVHWPDOYNOI-UHFFFAOYSA-N 0.000 claims description 10
- PBVARAUVAZZUHN-UHFFFAOYSA-N 5-(3,5-dimethoxyphenyl)-3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazole Chemical compound COC1=CC(OC)=CC(C=2ON=C(N=2)C=2N=CC(F)=CC=2)=C1 PBVARAUVAZZUHN-UHFFFAOYSA-N 0.000 claims description 10
- HFGWLRAJYOVQAY-UHFFFAOYSA-N 2-(3-bromophenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound BrC1=CC=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 HFGWLRAJYOVQAY-UHFFFAOYSA-N 0.000 claims description 9
- XKZXZXODZDSMKN-UHFFFAOYSA-N 3-[3-(5-methoxypyridin-2-yl)-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound N1=CC(OC)=CC=C1C1=NOC(C=2C=C(C=CC=2)C#N)=N1 XKZXZXODZDSMKN-UHFFFAOYSA-N 0.000 claims description 9
- DKASLOPISBVXCX-UHFFFAOYSA-N 3-pyridin-2-yl-5-[3-(trifluoromethoxy)phenyl]-1,2,4-oxadiazole Chemical compound FC(F)(F)OC1=CC=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 DKASLOPISBVXCX-UHFFFAOYSA-N 0.000 claims description 9
- FZTXNLFUEFOVRO-UHFFFAOYSA-N 3-pyridin-2-yl-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical group FC(F)(F)C1=CC=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 FZTXNLFUEFOVRO-UHFFFAOYSA-N 0.000 claims description 9
- GIHMKZCHBTWVSO-UHFFFAOYSA-N 5-(2,3-difluorophenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound FC1=CC=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1F GIHMKZCHBTWVSO-UHFFFAOYSA-N 0.000 claims description 9
- NFNZGNPPPSUBSN-UHFFFAOYSA-N 5-(3,5-dimethoxyphenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound COC1=CC(OC)=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 NFNZGNPPPSUBSN-UHFFFAOYSA-N 0.000 claims description 9
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
- XZDUVAVPEQYRJT-UHFFFAOYSA-N 3-(4-pyridin-2-yl-1,3-oxazol-2-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 XZDUVAVPEQYRJT-UHFFFAOYSA-N 0.000 claims description 8
- OTAZWJWYCGCZPY-UHFFFAOYSA-N 3-pyridin-2-yl-5-(2,3,6-trifluorophenyl)-1,2,4-oxadiazole Chemical compound FC1=CC=C(F)C(C=2ON=C(N=2)C=2N=CC=CC=2)=C1F OTAZWJWYCGCZPY-UHFFFAOYSA-N 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
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- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- MWFUWMAFXIIDOK-UHFFFAOYSA-N 5-(3,5-difluorophenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound FC1=CC(F)=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 MWFUWMAFXIIDOK-UHFFFAOYSA-N 0.000 claims description 6
- YYKRPCBJFTUNFZ-UHFFFAOYSA-N 5-(3-nitrophenyl)-3-pyridin-2-yl-1,2,4-oxadiazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 YYKRPCBJFTUNFZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- RJOREFFZIBPFKY-UHFFFAOYSA-N 2-(2,3-difluorophenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound FC1=CC=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1F RJOREFFZIBPFKY-UHFFFAOYSA-N 0.000 claims description 5
- LRFMDDYKWJYVBK-UHFFFAOYSA-N 2-(2,5-difluorophenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound FC1=CC=C(F)C(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 LRFMDDYKWJYVBK-UHFFFAOYSA-N 0.000 claims description 5
- ZLPWRJCQPWCDGU-UHFFFAOYSA-N 2-(2-bromo-5-methoxyphenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound COC1=CC=C(Br)C(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 ZLPWRJCQPWCDGU-UHFFFAOYSA-N 0.000 claims description 5
- DEMSILUPLXBKQE-UHFFFAOYSA-N 2-(2-chloro-5-methylsulfanylphenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound CSC1=CC=C(Cl)C(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 DEMSILUPLXBKQE-UHFFFAOYSA-N 0.000 claims description 5
- YXDVCVJVOFDWQF-UHFFFAOYSA-N 2-(2-chlorophenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound ClC1=CC=CC=C1C1=NC(C=2N=CC=CC=2)=CO1 YXDVCVJVOFDWQF-UHFFFAOYSA-N 0.000 claims description 5
- ASQZRZJOTGTSSV-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound ClC1=CC(Cl)=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 ASQZRZJOTGTSSV-UHFFFAOYSA-N 0.000 claims description 5
- YHRDDEHPQTZUOC-UHFFFAOYSA-N 2-(3,5-difluorophenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound FC1=CC(F)=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 YHRDDEHPQTZUOC-UHFFFAOYSA-N 0.000 claims description 5
- IUSLSOMMUPIHNA-UHFFFAOYSA-N 2-(3,5-dimethoxyphenyl)-4-(5-fluoropyridin-2-yl)-1,3-oxazole Chemical compound COC1=CC(OC)=CC(C=2OC=C(N=2)C=2N=CC(F)=CC=2)=C1 IUSLSOMMUPIHNA-UHFFFAOYSA-N 0.000 claims description 5
- LPMYOKHUPLYHGH-UHFFFAOYSA-N 2-(3,5-dimethoxyphenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound COC1=CC(OC)=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 LPMYOKHUPLYHGH-UHFFFAOYSA-N 0.000 claims description 5
- DVWPIPCIVDZTFL-UHFFFAOYSA-N 2-(3-chloro-5-fluorophenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound FC1=CC(Cl)=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 DVWPIPCIVDZTFL-UHFFFAOYSA-N 0.000 claims description 5
- SIWHIGOKGZLPDD-UHFFFAOYSA-N 2-(3-methoxyphenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound COC1=CC=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 SIWHIGOKGZLPDD-UHFFFAOYSA-N 0.000 claims description 5
- MMOZNJWTGXWZAK-UHFFFAOYSA-N 2-(3-methylphenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound CC1=CC=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 MMOZNJWTGXWZAK-UHFFFAOYSA-N 0.000 claims description 5
- VVAAKNGCCMGISN-UHFFFAOYSA-N 2-(3-nitrophenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2OC=C(N=2)C=2N=CC=CC=2)=C1 VVAAKNGCCMGISN-UHFFFAOYSA-N 0.000 claims description 5
- BWGHUEIUTYJJMM-UHFFFAOYSA-N 2-(5-chloro-2-methoxyphenyl)-4-pyridin-2-yl-1,3-oxazole Chemical compound COC1=CC=C(Cl)C=C1C1=NC(C=2N=CC=CC=2)=CO1 BWGHUEIUTYJJMM-UHFFFAOYSA-N 0.000 claims description 5
- KZOBYFBUONCLFZ-UHFFFAOYSA-N 3-(3-pyridin-2-yl-1,2,4-oxadiazol-5-yl)benzonitrile Chemical compound N#CC1=CC=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 KZOBYFBUONCLFZ-UHFFFAOYSA-N 0.000 claims description 5
- ACEMLHPTBCVQEO-UHFFFAOYSA-N 3-[3-(3-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound FC1=CC=CN=C1C1=NOC(C=2C=C(C=CC=2)C#N)=N1 ACEMLHPTBCVQEO-UHFFFAOYSA-N 0.000 claims description 5
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- JTCHHBMKZRITLW-UHFFFAOYSA-N 3-[3-(5-fluoropyridin-2-yl)-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound N1=CC(F)=CC=C1C1=NOC(C=2C=C(C=CC=2)C#N)=N1 JTCHHBMKZRITLW-UHFFFAOYSA-N 0.000 claims description 5
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- NEBUBOGLNXERLF-UHFFFAOYSA-N 3-chloro-5-(3-pyridin-2-yl-1,2,4-oxadiazol-5-yl)benzonitrile Chemical compound ClC1=CC(C#N)=CC(C=2ON=C(N=2)C=2N=CC=CC=2)=C1 NEBUBOGLNXERLF-UHFFFAOYSA-N 0.000 claims description 5
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
-
- 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
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14946499P | 1999-08-19 | 1999-08-19 | |
| US149464P | 1999-08-19 | ||
| PCT/US2000/022618 WO2001012627A1 (en) | 1999-08-19 | 2000-08-18 | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60023318D1 DE60023318D1 (de) | 2006-03-02 |
| DE60023318T2 true DE60023318T2 (de) | 2006-07-20 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60023318T Expired - Lifetime DE60023318T2 (de) | 1999-08-19 | 2000-08-18 | Heteropolycyclische verbindungen und ihre verwendung als antagonisten von metabotropen glutamatrezeptoren |
Country Status (27)
| Country | Link |
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| EP (1) | EP1210344B1 (https=) |
| JP (2) | JP3790472B2 (https=) |
| KR (1) | KR100875222B1 (https=) |
| CN (1) | CN1313465C (https=) |
| AT (1) | ATE307129T1 (https=) |
| AU (1) | AU780191B2 (https=) |
| BG (1) | BG65586B1 (https=) |
| BR (1) | BR0013427A (https=) |
| CA (1) | CA2381975A1 (https=) |
| CY (1) | CY1105253T1 (https=) |
| CZ (1) | CZ2002599A3 (https=) |
| DE (1) | DE60023318T2 (https=) |
| DK (1) | DK1210344T3 (https=) |
| EE (1) | EE200200079A (https=) |
| ES (1) | ES2250177T3 (https=) |
| HU (1) | HUP0202757A3 (https=) |
| IL (2) | IL148157A0 (https=) |
| IS (1) | IS6275A (https=) |
| MX (1) | MXPA02001764A (https=) |
| NO (1) | NO322460B1 (https=) |
| NZ (1) | NZ517221A (https=) |
| PL (1) | PL353825A1 (https=) |
| RU (1) | RU2296127C9 (https=) |
| SK (1) | SK2512002A3 (https=) |
| UA (1) | UA75871C2 (https=) |
| WO (1) | WO2001012627A1 (https=) |
| ZA (1) | ZA200201358B (https=) |
Families Citing this family (73)
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| US6660753B2 (en) | 1999-08-19 | 2003-12-09 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
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| US6916821B2 (en) | 2001-04-02 | 2005-07-12 | Brown University | Methods of treating disorders with Group I mGluR antagonists |
| DE60214846T2 (de) * | 2001-04-02 | 2007-05-16 | Brown University Research Foundation | Verwendung von mGLuR5 antagonists zur Herstellung von Medikamenten zur Behandlung von empfindlichen X Syndrome, Autismus und geistiger Zurückgebliebenheit |
| DE60223720T2 (de) * | 2001-12-18 | 2008-10-30 | Merck & Co., Inc. | Heteroaryl-substituierte pyrazol-modulatoren des metabotropen glutamatrezeptors-5 |
| DE60222698T2 (de) * | 2001-12-18 | 2008-06-19 | Merck & Co., Inc. | Heteroarylsubstituierte triazolmodulatoren des metabotropen glutamatarezeptors 5 |
| WO2003053922A2 (en) * | 2001-12-19 | 2003-07-03 | Merck & Co., Inc. | Heteroaryl substituted imidazole modulators of metabotropic glutamate receptor-5 |
| EP1485093B1 (en) * | 2002-03-12 | 2010-11-03 | Merck Sharp & Dohme Corp. | Di-aryl substituted tetrazole modulators of metabotropic glutamate receptor-5 |
| SE0201943D0 (sv) * | 2002-06-20 | 2002-06-20 | Astrazeneca Ab | New use |
| US7964609B2 (en) | 2002-06-20 | 2011-06-21 | Astrazeneca Ab | Use of mGluR5 antagonists for the treatment of gerd |
| TW200424183A (en) * | 2002-08-09 | 2004-11-16 | Nps Pharma Inc | New compounds |
| US7074809B2 (en) | 2002-08-09 | 2006-07-11 | Astrazeneca Ab | Compounds |
| WO2004014881A2 (en) | 2002-08-09 | 2004-02-19 | Astra Zeneca Ab | '1,2,4'oxadiazoles as modulators of metabotropic glutamate receptor-5 |
| GB0303503D0 (en) * | 2003-02-14 | 2003-03-19 | Novartis Ag | Organic compounds |
| EP1613617A4 (en) * | 2003-04-04 | 2009-02-18 | Merck & Co Inc | METABOTROPIC GLUTAMATE RECEPTOR-5 DIARYLSUBSTITUTED TRIAZOLE MODULATORS |
| AU2004240586A1 (en) * | 2003-05-15 | 2004-12-02 | Merck & Co., Inc. | 3-(2-amino-1-azacyclyl)-5-aryl-1,2,4-oxadiazoles as S1P receptor agonists |
| WO2005060961A2 (en) * | 2003-12-18 | 2005-07-07 | Astrazeneca Ab | Treatment of transient lower esophageal sphincter relaxations (tlesrs) and gastro-esophageal reflux disease (gerd) |
| JP4958560B2 (ja) * | 2003-12-24 | 2012-06-20 | プロシディオン・リミテッド | Ｇｐｃｒ受容体作動薬としてのヘテロ環誘導体 |
| DE602005008558D1 (de) * | 2004-02-18 | 2008-09-11 | Astrazeneca Ab | Kondensierte heterocyclische verbindungen und deren verwendung als antagonisten des metabotropen reznkungen |
| US7585881B2 (en) | 2004-02-18 | 2009-09-08 | Astrazeneca Ab | Additional heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| US20070185100A1 (en) * | 2004-02-18 | 2007-08-09 | Astrazeneca Ab | Poly-heterocyclic compounds and their use as metabotropic glutamate receptor antagonists |
| TW200538108A (en) | 2004-02-19 | 2005-12-01 | Astrazeneca Ab | Fused heterocyclic compounds and their use as metabotropic glutamate receptor antagonists |
| US7858800B2 (en) * | 2004-06-30 | 2010-12-28 | Banyu Pharmaceutical Co., Ltd. | Biaryl derivatives |
| KR100621192B1 (ko) * | 2004-10-13 | 2006-09-19 | 한국화학연구원 | 무스카린 수용체 작용물질로서 작용하는1,2,3,4-테트라하이드로피리미디닐-1,2,4-옥사다이아졸유도체와 이의 제조방법 |
| JP4557685B2 (ja) | 2004-11-15 | 2010-10-06 | 独立行政法人理化学研究所 | 蛍光蛋白質 |
| BRPI0606644A2 (pt) | 2005-01-14 | 2009-07-14 | Hoffmann La Roche | derivados de 4-carboxamida tiazola |
| GB0510142D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds A1 |
| CN101203220A (zh) * | 2005-06-28 | 2008-06-18 | 阿斯利康(瑞典)有限公司 | 新用途 |
| PL1907382T3 (pl) | 2005-07-26 | 2016-01-29 | Bial Portela & Ca Sa | Pochodne nitrokatecholowe jako inhibitory COMT |
| UY29796A1 (es) | 2005-09-29 | 2007-04-30 | Astrazeneca Ab | Nuevos compuestos para el tratamiento de trastornos neurológicos, psiquiátricos o del dolor |
| RU2425834C2 (ru) | 2005-11-08 | 2011-08-10 | Ф. Хоффманн-Ля Рош Аг | ПРОИЗВОДНЫЕ ТИАЗОЛО[4,5-c]ПИРИДИНА В КАЧЕСТВЕ АНТАГОНИСТОВ РЕЦЕПТОРОВ mGluR5 |
| US7951824B2 (en) | 2006-02-17 | 2011-05-31 | Hoffman-La Roche Inc. | 4-aryl-pyridine-2-carboxyamide derivatives |
| PL2003132T3 (pl) * | 2006-04-03 | 2014-10-31 | Astellas Pharma Inc | Pochodne oksadiazolu jako agoniści S1P1 |
| EP1845097A1 (en) | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
| WO2008028903A2 (en) * | 2006-09-04 | 2008-03-13 | Neurosearch A/S | Pharmaceutical combinations of a nicotine receptor modulator and a cognitive enhancer |
| PT2069336E (pt) | 2006-09-07 | 2013-03-07 | Actelion Pharmaceuticals Ltd | Derivados de piridin-4-ilo como agentes imunomoduladores |
| PL2069335T3 (pl) | 2006-09-08 | 2013-05-31 | Actelion Pharmaceuticals Ltd | Pochodne pirydyn-3-ylu jako środki immunomodulujące |
| ES2393412T3 (es) | 2006-09-21 | 2012-12-21 | Actelion Pharmaceuticals Ltd. | Derivados de fenilo y su uso como inmunomoduladores |
| BRPI0721213B1 (pt) | 2007-01-31 | 2021-11-09 | Bial - Portela & Ca, S.A. | Uso de nitrocatecóis substituídos, e embalagem |
| BRPI0808789A2 (pt) | 2007-03-16 | 2014-08-12 | Actelion Pharmaceuticals Ltd | Compostos e composição farmacêutica de derivados aminopiridina e uso destes |
| PT2195311E (pt) | 2007-08-17 | 2011-05-25 | Actelion Pharmaceuticals Ltd | Derivados de piridina como moduladores do receptor s1p1/edg1 |
| JP2011502148A (ja) | 2007-10-31 | 2011-01-20 | メルク・シャープ・エンド・ドーム・コーポレイション | 疼痛の治療用としてのｐ２ｘ３受容体アンタゴニスト |
| KR20100092473A (ko) | 2007-11-01 | 2010-08-20 | 액테리온 파마슈티칼 리미티드 | 신규한 피리미딘 유도체 |
| CN101903356B (zh) * | 2007-12-20 | 2013-05-22 | 拜耳知识产权有限责任公司 | 4-(4-氰基-2-硫代芳基)二氢嘧啶酮和它们的使用 |
| US8188131B2 (en) | 2008-02-07 | 2012-05-29 | Massachusetts Eye & Ear Infirmary | Compounds that enhance Atoh1 expression |
| CA2715317A1 (en) | 2008-03-07 | 2009-09-11 | Actelion Pharmaceuticals Ltd | Novel aminomethyl benzene derivatives |
| WO2009116882A1 (en) | 2008-03-17 | 2009-09-24 | Portela & Ca., S.A. | 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 |
| MX2011004570A (es) | 2008-10-31 | 2011-06-17 | Merck Sharp & Dohme | Antagonistas del receptor p2x3 para el tratamiento del dolor. |
| DE102008057344A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Aminoalkyl-substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102009041241A1 (de) | 2009-09-11 | 2011-08-04 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102009041242A1 (de) | 2009-09-11 | 2011-12-15 | Bayer Schering Pharma Aktiengesellschaft | Heterocyclisch substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102008057364A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102008057343A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Heterocyclisch substituierte Aryl-Verbindungen und ihre Verwendung |
| AU2010229142A1 (en) | 2009-03-23 | 2011-10-13 | Merck Sharp & Dohme Corp. | P2X3, receptor antagonists for treatment of pain |
| US8569512B2 (en) | 2009-03-23 | 2013-10-29 | Merck Sharp & Dohme Corp. | P2X3 receptor antagonists for treatment of pain |
| WO2010111059A1 (en) | 2009-03-23 | 2010-09-30 | Merck Sharp & Dohme Corp. | P2x3 receptor antagonists for treatment of pain |
| PT2413912T (pt) | 2009-04-01 | 2019-06-11 | Bial Portela & Ca Sa | Formulações farmacêuticas compreendendo derivados de nitrocatecol e métodos para as produzir |
| AU2010236685A1 (en) * | 2009-04-13 | 2011-12-01 | Irm Llc | Compositions and methods for modulating retinol binding to retinol binding protein 4 (RBP4) |
| CA2767585C (en) | 2009-07-16 | 2017-09-26 | Actelion Pharmaceuticals Ltd | Pyridin-4-yl derivatives |
| WO2011109398A2 (en) | 2010-03-02 | 2011-09-09 | President And Fellows Of Harvard College | Methods and compositions for treatment of angelman syndrome and autism spectrum disorders |
| MA34910B1 (fr) | 2011-01-19 | 2014-02-01 | Actelion Pharmaceuticals Ltd | Dérivés de 2-methoxy-pyridin-4-yl |
| US20140045900A1 (en) | 2011-02-11 | 2014-02-13 | Bial-Portela & Ca, S.A. | Administration regime for nitrocatechols |
| JP6456143B2 (ja) | 2011-12-13 | 2019-01-23 | ノヴィファーマ，エス．アー． | カテコール−ｏ−メチル転移酵素阻害剤を調製するための中間体として有用な化学的化合物 |
| JP5946288B2 (ja) * | 2012-02-24 | 2016-07-06 | 公立大学法人名古屋市立大学 | 新規ヒドロキサム酸誘導体及びその用途 |
| US9232800B2 (en) | 2013-02-15 | 2016-01-12 | Monsanto Technology Llc | 3,5-disubstituted-4,5-dihydro-1,2,4-oxadiazoles and compositions and methods for controlling nematode pests |
| EP2853532B1 (en) * | 2013-09-28 | 2020-12-09 | Instytut Farmakologii Polskiej Akademii Nauk | 1,2,4-oxadiazole derivatives as allosteric modulators of metabotropic glutamate receptors belonging to group III |
| RU2017120184A (ru) | 2014-11-28 | 2018-12-28 | БИАЛ - ПОРТЕЛА ЭНД Ка, С.А. | Лекарства для замедления течения болезни паркинсона |
| PH12017502097B1 (en) | 2015-05-20 | 2023-05-05 | Idorsia Pharmaceuticals Ltd | Crystalline form of the compound (s)-3-{4-[5-(2-cyclopentyl-6-methoxy-pyridin-4-yl)-[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methyl-phenoxy}-propane-1,2-diol |
| AU2016281346B2 (en) | 2015-06-23 | 2020-01-02 | Kissei Pharmaceutical Co., Ltd. | Pyrazole derivative, or pharmaceutically acceptable salt thereof |
| EP3436009B1 (en) * | 2016-03-30 | 2024-03-06 | Sinntaxis AB | Negative allosteric modulators of mglur5 for use in the treatment of mature brain damages. |
| FI3904350T3 (fi) * | 2018-04-12 | 2023-11-15 | Bayer Ag | N-(syklopropyylimetyyli)-5-(metyylisulfonyyli)-n-{1-[1-(pyrimidin-2-yyli)-1h-1,2,4-triatsol-5-yyli]etyyli}bentsamidijohdannaisia ja vastaavia pyridiinikarboksamidijohdannaisia tuholaistorjunta-aineina |
| KR102276327B1 (ko) * | 2019-06-25 | 2021-07-12 | 연세대학교 산학협력단 | 신규 옥사다이아졸 화합물 및 이를 포함하는 당뇨 예방 또는 치료용 조성물 |
| AU2020341464A1 (en) * | 2019-09-05 | 2022-04-21 | Trevena, Inc. | Methods of treating epilepsy using the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE1149011B (de) * | 1960-04-05 | 1963-05-22 | Hoechst Ag | Verfahren zur Herstellung von 3, 5-disubstituierten 1, 2, 4-Oxdiazolen |
| US3647809A (en) * | 1968-04-26 | 1972-03-07 | Chinoin Gyogyszer Es Vegyeszet | Certain pyridyl-1 2 4-oxadiazole derivatives |
| US4003909A (en) * | 1974-07-22 | 1977-01-18 | E. R. Squibb & Sons, Inc. | [(1,2,4-Oxadiazol-3-yl)phenyl]carbamic or thiocarbamic acid esters |
| US4022901A (en) * | 1975-03-05 | 1977-05-10 | E. R. Squibb & Sons, Inc. | 3-Pyridinyl-5-isothiocyanophenyl oxadiazoles |
| AU675484B2 (en) * | 1993-03-24 | 1997-02-06 | Neurosearch A/S | Benzimidazole compounds, their use and preparation |
| US5554630A (en) * | 1993-03-24 | 1996-09-10 | Neurosearch A/S | Benzimidazole compounds |
| WO1994022846A1 (en) * | 1993-03-30 | 1994-10-13 | Pfizer Inc. | Compounds enhancing antitumor activity of other cytotoxic agents |
| PL183853B1 (pl) * | 1995-04-21 | 2002-07-31 | Neurosearch As | Nowa pochodna benzimidazolu i środek farmaceutyczny |
| AU6526896A (en) * | 1995-07-22 | 1997-02-18 | Rhone-Poulenc Rorer Limited | Substituted aromatic compounds and their pharmaceutical use |
| DE19643037A1 (de) * | 1996-10-18 | 1998-04-23 | Boehringer Ingelheim Kg | Neue Oxadiazole, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel |
| CN1158264C (zh) * | 1997-11-21 | 2004-07-21 | Nps药物有限公司 | 用于治疗中枢神经系统疾病的代谢性谷氨酸受体拮抗剂 |
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2000
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- 2000-08-18 PL PL00353825A patent/PL353825A1/xx not_active Application Discontinuation
- 2000-08-18 DE DE60023318T patent/DE60023318T2/de not_active Expired - Lifetime
- 2000-08-18 UA UA2002032079A patent/UA75871C2/uk unknown
- 2000-08-18 DK DK00955657T patent/DK1210344T3/da active
- 2000-08-18 SK SK251-2002A patent/SK2512002A3/sk unknown
- 2000-08-18 AT AT00955657T patent/ATE307129T1/de active
- 2000-08-18 ES ES00955657T patent/ES2250177T3/es not_active Expired - Lifetime
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- 2000-08-18 RU RU2002107201/04A patent/RU2296127C9/ru not_active IP Right Cessation
- 2000-08-18 NZ NZ517221A patent/NZ517221A/en not_active IP Right Cessation
- 2000-08-18 EE EEP200200079A patent/EE200200079A/xx unknown
- 2000-08-18 CA CA002381975A patent/CA2381975A1/en not_active Abandoned
- 2000-08-18 CN CNB008145024A patent/CN1313465C/zh not_active Expired - Fee Related
- 2000-08-18 IL IL14815700A patent/IL148157A0/xx active IP Right Grant
- 2000-08-18 CZ CZ2002599A patent/CZ2002599A3/cs unknown
- 2000-08-18 EP EP00955657A patent/EP1210344B1/en not_active Expired - Lifetime
- 2000-08-18 MX MXPA02001764A patent/MXPA02001764A/es active IP Right Grant
- 2000-08-18 BR BR0013427-9A patent/BR0013427A/pt not_active Application Discontinuation
- 2000-08-18 HU HU0202757A patent/HUP0202757A3/hu unknown
- 2000-08-18 WO PCT/US2000/022618 patent/WO2001012627A1/en not_active Ceased
- 2000-08-18 JP JP2001517525A patent/JP3790472B2/ja not_active Expired - Fee Related
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- 2002-02-14 IL IL148157A patent/IL148157A/en not_active IP Right Cessation
- 2002-02-18 IS IS6275A patent/IS6275A/is unknown
- 2002-02-18 ZA ZA200201358A patent/ZA200201358B/xx unknown
- 2002-02-19 NO NO20020823A patent/NO322460B1/no not_active IP Right Cessation
- 2002-03-07 BG BG106493A patent/BG65586B1/bg unknown
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2005
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2006
- 2006-01-25 JP JP2006016914A patent/JP2006143746A/ja active Pending
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Owner name: ASTRAZENECA AB, SOEDERTAELJE, SE |