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
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- 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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Psychology (AREA)
- Rheumatology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Urology & Nephrology (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
ID=22530400
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 (OSRAM) |
| JP (2) | JP3790472B2 (OSRAM) |
| KR (1) | KR100875222B1 (OSRAM) |
| CN (1) | CN1313465C (OSRAM) |
| AT (1) | ATE307129T1 (OSRAM) |
| AU (1) | AU780191B2 (OSRAM) |
| BG (1) | BG65586B1 (OSRAM) |
| BR (1) | BR0013427A (OSRAM) |
| CA (1) | CA2381975A1 (OSRAM) |
| CY (1) | CY1105253T1 (OSRAM) |
| CZ (1) | CZ2002599A3 (OSRAM) |
| DE (1) | DE60023318T2 (OSRAM) |
| DK (1) | DK1210344T3 (OSRAM) |
| EE (1) | EE200200079A (OSRAM) |
| ES (1) | ES2250177T3 (OSRAM) |
| HU (1) | HUP0202757A3 (OSRAM) |
| IL (2) | IL148157A0 (OSRAM) |
| IS (1) | IS6275A (OSRAM) |
| MX (1) | MXPA02001764A (OSRAM) |
| NO (1) | NO322460B1 (OSRAM) |
| NZ (1) | NZ517221A (OSRAM) |
| PL (1) | PL353825A1 (OSRAM) |
| RU (1) | RU2296127C9 (OSRAM) |
| SK (1) | SK2512002A3 (OSRAM) |
| UA (1) | UA75871C2 (OSRAM) |
| WO (1) | WO2001012627A1 (OSRAM) |
| ZA (1) | ZA200201358B (OSRAM) |
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| EP1392363B1 (en) | 2001-04-02 | 2006-09-20 | Brown University Research Foundation | Use of mGLuR5 antagonists in the manufacture of a medicament in the treatment of Fragile X syndrome, Autism and Mental Retardation |
| US6916821B2 (en) | 2001-04-02 | 2005-07-12 | Brown University | Methods of treating disorders with Group I mGluR antagonists |
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| AU2002359714B2 (en) * | 2001-12-18 | 2006-12-21 | Merck Sharp & Dohme Corp. | Heteroaryl substituted pyrazole modulators of metabotropic glutamate receptor-5 |
| EP1458385A4 (en) * | 2001-12-19 | 2005-12-21 | Merck & Co Inc | METABOTROPIC GLUTAMATE RECEPTOR 5-HETEROARYL-SUBSTITUTED IMIDAZOLE MODULATORS |
| US7592337B2 (en) * | 2002-03-12 | 2009-09-22 | Merck & Co., Inc. | Di-aryl substituted tetrazole modulators of metabotropic glutamate receptor-5 |
| US7964609B2 (en) | 2002-06-20 | 2011-06-21 | Astrazeneca Ab | Use of mGluR5 antagonists for the treatment of gerd |
| SE0201943D0 (sv) * | 2002-06-20 | 2002-06-20 | Astrazeneca Ab | New use |
| PL375256A1 (en) | 2002-08-09 | 2005-11-28 | Astra Zeneca Ab | 1,2,4-oxadiazoles as modulators of metabotropic glutamate receptor-5 |
| US20040132726A1 (en) * | 2002-08-09 | 2004-07-08 | Astrazeneca Ab And Nps Pharmaceuticals, Inc. | New compounds |
| AU2003264018A1 (en) * | 2002-08-09 | 2004-02-25 | Astrazeneca Ab | Compounds having an activity at metabotropic glutamate receptors |
| GB0303503D0 (en) * | 2003-02-14 | 2003-03-19 | Novartis Ag | Organic compounds |
| US7268151B2 (en) * | 2003-04-04 | 2007-09-11 | Merck & Co., Inc. | Di-aryl substituted triazole modulators of metabotropic glutamate receptor-5 |
| EP1625123A4 (en) * | 2003-05-15 | 2007-08-29 | Merck & Co Inc | 3- (2-AMINO-1-AZACYCLYL) -5-ARYL-1,2,4-OXADIAZOLE 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) |
| BRPI0418149A (pt) * | 2003-12-24 | 2007-04-17 | Prosidion Ltd | derivados heterocìclicos como agonistas do receptor de gprc |
| NZ548693A (en) * | 2004-02-18 | 2010-05-28 | Astrazeneca Ab | Polyheterocyclic compounds and their use as metabotropic glutamate receptor antagonists |
| SI1716152T1 (sl) * | 2004-02-18 | 2008-12-31 | Astrazeneca Ab | Kondenzirane heterociklične spojine in njihova uporaba kot antagonisti metabotropnega receptorja za zdravljenje gastrointestinalnih motenj |
| US7585881B2 (en) * | 2004-02-18 | 2009-09-08 | Astrazeneca Ab | Additional heteropolycyclic 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 |
| JP4803034B2 (ja) * | 2004-06-30 | 2011-10-26 | Ｍｓｄ株式会社 | ビアリール誘導体 |
| 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 |
| AU2006205920B2 (en) | 2005-01-14 | 2012-11-15 | F. Hoffmann-La Roche Ag | Thiazole-4-carboxamide derivatives as mGluR5 antagonists |
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| CN101203220A (zh) * | 2005-06-28 | 2008-06-18 | 阿斯利康(瑞典)有限公司 | 新用途 |
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| UY29796A1 (es) | 2005-09-29 | 2007-04-30 | Astrazeneca Ab | Nuevos compuestos para el tratamiento de trastornos neurológicos, psiquiátricos o del dolor |
| WO2007054436A2 (en) | 2005-11-08 | 2007-05-18 | F. Hoffmann-La Roche Ag | Thiazolo [4 , 5-c] pyridine derivatives as mglu5 receptor antagonists |
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| EP1845097A1 (en) | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
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| EP2069318B1 (en) | 2006-09-21 | 2012-09-12 | Actelion Pharmaceuticals Ltd. | Phenyl derivatives and their use as immunomodulators |
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| MX2009009597A (es) | 2007-03-16 | 2009-09-16 | Actelion Pharmaceuticals Ltd | Derivados de amino-piridina como agonistas del receptor s1p1/edg1. |
| CN102648198B (zh) | 2007-08-17 | 2015-04-01 | 埃科特莱茵药品有限公司 | 作为s1p1/edg1受体调节剂的吡啶衍生物 |
| WO2009058298A1 (en) | 2007-10-31 | 2009-05-07 | Merck & Co., Inc. | P2x3, receptor antagonists for treatment of pain |
| BRPI0818804A2 (pt) | 2007-11-01 | 2015-04-22 | Actelion Pharmaceuticals Ltd | Composto derivado de pirimidina, composição farmacêutica que o compreende e uso desse composto. |
| 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 |
| EP2732819B1 (en) | 2008-02-07 | 2019-10-16 | Massachusetts Eye & Ear Infirmary | Compounds that enhance Atoh-1 expression |
| EP2262782B1 (en) | 2008-03-07 | 2012-07-04 | Actelion Pharmaceuticals Ltd. | Novel aminomethyl benzene derivatives |
| BRPI0908731A2 (pt) | 2008-03-17 | 2017-05-16 | Bial - Portela & C A S A | formas cristalinas de 5-[3-(2,5-dicloro-4,6-dimetil-1-óxi-piridina-3-il)[1,2,4]oxadiazol-5-il]-3-nitrobenzeno-1,2-diol |
| AU2009309019B2 (en) | 2008-10-31 | 2014-11-13 | Merck Sharp & Dohme Llc | P2X3, receptor antagonists for treatment of pain |
| DE102008057343A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Heterocyclisch 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 |
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| DE102008057344A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Aminoalkyl-substituierte Aryl-Verbindungen und ihre Verwendung |
| DE102008057364A1 (de) | 2008-11-14 | 2010-05-20 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Aryl-Verbindungen und ihre Verwendung |
| WO2010111060A1 (en) | 2009-03-23 | 2010-09-30 | Merck Sharp & Dohme Corp. | P2x3, receptor antagonists for treatment of pain |
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| EP2544688B1 (en) | 2010-03-02 | 2016-09-07 | President and Fellows of Harvard College | Methods and compositions for treatment of angelman syndrome |
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| US20140045900A1 (en) | 2011-02-11 | 2014-02-13 | Bial-Portela & Ca, S.A. | Administration regime for nitrocatechols |
| CA2858025C (en) | 2011-12-13 | 2020-09-22 | Bial-Portela & Ca., S.A. | 5-[3-(2,5-dichloro-4,6-dimethyl-1-oxy-pyridin-3-yl)-[1,2,4]oxadiazol-5-yl]-2-hydroxy-3-methoxy-1-nitrobenzene as an intermediate to prepare a catechol-o-methyltransferase inhibitor |
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| 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 |
| US10385043B2 (en) | 2015-05-20 | 2019-08-20 | 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 |
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| JP2019515892A (ja) * | 2016-03-30 | 2019-06-13 | シンタクシス・エービー | 成熟脳損傷の治療における使用のためのｍＧｌｕＲ５のネガティブアロステリックモジュレーター |
| BR112020018006A2 (pt) * | 2018-04-12 | 2021-01-12 | Bayer Aktiengesellschaft | Derivados de n-(ciclopropilmetil)-5-(metilsulfonil)-n-{1-[1-(pirimidin-2-il)-1h-1,2,4-triazol-5-il]etil}benzamida e os derivados correspondentes de piridina-carboxamida como pesticidas |
| KR102276327B1 (ko) * | 2019-06-25 | 2021-07-12 | 연세대학교 산학협력단 | 신규 옥사다이아졸 화합물 및 이를 포함하는 당뇨 예방 또는 치료용 조성물 |
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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 |
| IL31990A (en) * | 1968-04-26 | 1974-05-16 | Chinoin Gyogyszer Es Vegyeszet | Pyridyl 1,2,4-oxadiazole derivatives,process for the preparation thereof and pharmaceutical compositions containing same |
| 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 |
| US5554630A (en) * | 1993-03-24 | 1996-09-10 | Neurosearch A/S | Benzimidazole compounds |
| AU675484B2 (en) * | 1993-03-24 | 1997-02-06 | Neurosearch A/S | Benzimidazole compounds, their use and preparation |
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| ATE210132T1 (de) * | 1995-04-21 | 2001-12-15 | Neurosearch As | Benzmidazolverbindungen und ihre verwendung als modulatoren des gabaa-rezeptor-komplexes |
| 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 |
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2000
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- 2000-08-18 CZ CZ2002599A patent/CZ2002599A3/cs unknown
- 2000-08-18 RU RU2002107201/04A patent/RU2296127C9/ru not_active IP Right Cessation
- 2000-08-18 AU AU67824/00A patent/AU780191B2/en not_active Ceased
- 2000-08-18 UA UA2002032079A patent/UA75871C2/uk unknown
- 2000-08-18 EE EEP200200079A patent/EE200200079A/xx unknown
- 2000-08-18 WO PCT/US2000/022618 patent/WO2001012627A1/en not_active Ceased
- 2000-08-18 SK SK251-2002A patent/SK2512002A3/sk unknown
- 2000-08-18 JP JP2001517525A patent/JP3790472B2/ja not_active Expired - Fee Related
- 2000-08-18 PL PL00353825A patent/PL353825A1/xx not_active Application Discontinuation
- 2000-08-18 CA CA002381975A patent/CA2381975A1/en not_active Abandoned
- 2000-08-18 BR BR0013427-9A patent/BR0013427A/pt not_active Application Discontinuation
- 2000-08-18 DE DE60023318T patent/DE60023318T2/de not_active Expired - Lifetime
- 2000-08-18 NZ NZ517221A patent/NZ517221A/en not_active IP Right Cessation
- 2000-08-18 KR KR1020027002120A patent/KR100875222B1/ko not_active Expired - Fee Related
- 2000-08-18 IL IL14815700A patent/IL148157A0/xx active IP Right Grant
- 2000-08-18 CN CNB008145024A patent/CN1313465C/zh not_active Expired - Fee Related
- 2000-08-18 ES ES00955657T patent/ES2250177T3/es not_active Expired - Lifetime
- 2000-08-18 MX MXPA02001764A patent/MXPA02001764A/es active IP Right Grant
- 2000-08-18 DK DK00955657T patent/DK1210344T3/da active
- 2000-08-18 AT AT00955657T patent/ATE307129T1/de active
- 2000-08-18 EP EP00955657A patent/EP1210344B1/en not_active Expired - Lifetime
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2002
- 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
- 2005-12-09 CY CY20051101521T patent/CY1105253T1/el unknown
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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 |