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)
- 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)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Psychology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Hospice & Palliative Care (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 |
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| BR (1) | BR0013427A (enExample) |
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| ES (1) | ES2250177T3 (enExample) |
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| IL (2) | IL148157A0 (enExample) |
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| MX (1) | MXPA02001764A (enExample) |
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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 |
| EP1379525B1 (en) * | 2001-02-21 | 2007-10-10 | Nps Pharmaceuticals, Inc. | Heteropolycyclic compounds and their use as metabotropic glutamate receptor antagonists |
| ES2272754T3 (es) | 2001-04-02 | 2007-05-01 | Brown University Research Foundation | Uso de antagonistas mglur5 en la fabricacion de un medicamento en el tratamiento de sindrome x fragil, autismo y retardo mental. |
| US6916821B2 (en) | 2001-04-02 | 2005-07-12 | Brown University | Methods of treating disorders with Group I mGluR antagonists |
| EP1458383B1 (en) * | 2001-12-18 | 2007-11-21 | Merck & Co., Inc. | Heteroaryl substituted pyrazole modulators of metabotropic glutamate receptor-5 |
| AU2002366388B2 (en) * | 2001-12-18 | 2008-09-18 | Merck & Co., Inc. | Heteroaryl substituted triazole modulators of metabotropic glutamate receptor-5 |
| JP2005516950A (ja) * | 2001-12-19 | 2005-06-09 | メルク エンド カムパニー インコーポレーテッド | 代謝型グルタミン酸受容体−５のヘテロアリール置換イミダゾールモジュレータ |
| JP4493341B2 (ja) * | 2002-03-12 | 2010-06-30 | メルク・シャープ・エンド・ドーム・コーポレイション | 代謝型グルタメート受容体−５の二アリール置換テトラゾールモジュレータ |
| 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 |
| TW200424183A (en) * | 2002-08-09 | 2004-11-16 | Nps Pharma Inc | New compounds |
| CN1894241A (zh) | 2002-08-09 | 2007-01-10 | 阿斯利康(瑞典)有限公司 | 作为代谢型谷氨酸受体－5调节剂的“1,2,4” 噁二唑 |
| WO2004014902A2 (en) * | 2002-08-09 | 2004-02-19 | Astrazeneca Ab | Compounds having an activity at metabotropic glutamate receptors |
| GB0303503D0 (en) * | 2003-02-14 | 2003-03-19 | Novartis Ag | Organic compounds |
| AU2004227833B2 (en) * | 2003-04-04 | 2009-10-01 | Merck & Co., Inc. | Di-aryl substituted triazole modulators of metabotropic glutamate receptor-5 |
| JP2006528980A (ja) * | 2003-05-15 | 2006-12-28 | メルク エンド カムパニー インコーポレーテッド | Ｓ１ｐ受容体作働薬としての３−（２−アミノ−１−アザシクロ）−５−アリール−１，２，４−オキサジアゾール類 |
| WO2005060961A2 (en) * | 2003-12-18 | 2005-07-07 | Astrazeneca Ab | Treatment of transient lower esophageal sphincter relaxations (tlesrs) and gastro-esophageal reflux disease (gerd) |
| WO2005061489A1 (en) * | 2003-12-24 | 2005-07-07 | Prosidion Limited | Heterocyclic derivatives as gpcr receptor agonists |
| MY152888A (en) * | 2004-02-18 | 2014-11-28 | Astrazeneca Ab | Fused heterocyclic compounds and their use as metabotropic glutamate receptor antagonists. |
| JP2007523181A (ja) * | 2004-02-18 | 2007-08-16 | アストラゼネカ アクチボラグ | ポリヘテロ環式化合物、および、代謝型グルタミン酸受容体アンタゴニストとしてのそれらの使用 |
| 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 |
| WO2006004142A1 (ja) * | 2004-06-30 | 2006-01-12 | Banyu Pharmaceutical Co., Ltd. | 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 |
| CA2593439C (en) | 2005-01-14 | 2014-02-25 | F. Hoffmann-La Roche Ag | Thiazole-4-carboxamide derivatives as mglur5 antagonists |
| GB0510142D0 (en) * | 2005-05-18 | 2005-06-22 | Addex Pharmaceuticals Sa | Novel compounds A1 |
| WO2007001973A1 (en) * | 2005-06-28 | 2007-01-04 | Astrazeneca Ab | New use |
| US8168793B2 (en) | 2005-07-26 | 2012-05-01 | Portela & Ca., S.A. | Nitrocatechol derivatives as COMT inhibitors |
| AR058807A1 (es) | 2005-09-29 | 2008-02-27 | Astrazeneca Ab | 5-(fenilisoxazoletoxi)-triazol-3-il piridinas sustituidas, para el tratamiento de trastornos mediados por el receptor mglur5 |
| BRPI0618636A2 (pt) | 2005-11-08 | 2011-09-06 | Hoffmann La Roche | derivados de tiazolo [4,5-c]piridina |
| US7951824B2 (en) | 2006-02-17 | 2011-05-31 | Hoffman-La Roche Inc. | 4-aryl-pyridine-2-carboxyamide derivatives |
| JP5099005B2 (ja) * | 2006-04-03 | 2012-12-12 | アステラス製薬株式会社 | ヘテロ化合物 |
| EP1845097A1 (en) | 2006-04-10 | 2007-10-17 | Portela & Ca., S.A. | Oxadiazole derivatives as COMT inhibitors |
| EP2083921A2 (en) * | 2006-09-04 | 2009-08-05 | Neurosearch A/S | Pharmaceutical combinations of a nicotine receptor modulator and a cognitive enhancer |
| PL2069336T3 (pl) | 2006-09-07 | 2013-05-31 | Idorsia Pharmaceuticals Ltd | Pochodne pirydyn-4-ylu jako środki immunomodulujące |
| AU2007292992B2 (en) | 2006-09-08 | 2013-01-10 | Actelion Pharmaceuticals Ltd | Pyridin-3-yl derivatives as immunomodulating agents |
| ES2393412T3 (es) | 2006-09-21 | 2012-12-21 | Actelion Pharmaceuticals Ltd. | Derivados de fenilo y su uso como inmunomoduladores |
| PL2481410T3 (pl) | 2007-01-31 | 2017-03-31 | Bial - Portela & Ca., S.A. | Pochodne nitrokatecholu jako inhibitory COMT podawane w określonym schemacie dawkowania |
| SI2125797T1 (sl) | 2007-03-16 | 2014-03-31 | Actelion Pharmaceuticals Ltd. | Derivati amino-piridina kot agonisti receptorja s1p1/edg1 |
| ES2361463T3 (es) | 2007-08-17 | 2011-06-17 | Actelion Pharmaceuticals Ltd. | Derivados de piridina como moduladores del receptor s1p1/edg1. |
| EP2215049B1 (en) | 2007-10-31 | 2019-06-12 | Merck Sharp & Dohme Corp. | P2x3, receptor antagonists for treatment of pain |
| EP2217594B1 (en) | 2007-11-01 | 2014-01-08 | Actelion Pharmaceuticals Ltd. | Novel pyrimidine derivatives |
| SI2234985T1 (sl) * | 2007-12-20 | 2012-06-29 | Bayer Pharma AG | 4-(4-ciano-2-tioaril)dihidropirimidinoni in njihova uporaba |
| AU2009212135B2 (en) | 2008-02-07 | 2014-08-21 | Massachusetts Eye & Ear Infirmary | Compounds that enhance Atoh-1 expression |
| CA2715317A1 (en) | 2008-03-07 | 2009-09-11 | Actelion Pharmaceuticals Ltd | Novel aminomethyl benzene derivatives |
| CL2009000628A1 (es) | 2008-03-17 | 2010-04-09 | Bial Portela & Companhia S A | Forma cristalina 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, composicion farmaceutica que la comprende, proceso para obtenerla y su uso para tratar trastornos del animo, enfermedad de parkinson y trastornos parkinsonianos, alteraciones gastrointestinales, entre otros. |
| US8598209B2 (en) | 2008-10-31 | 2013-12-03 | Merck Sharp & Dohme Corp. | P2X3, receptor antagonists for treatment of pain |
| 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 |
| DE102009041242A1 (de) | 2009-09-11 | 2011-12-15 | Bayer Schering Pharma Aktiengesellschaft | Heterocyclisch 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 |
| DE102009041241A1 (de) | 2009-09-11 | 2011-08-04 | Bayer Schering Pharma Aktiengesellschaft, 13353 | Substituierte Aryl-Verbindungen und ihre Verwendung |
| EP2411001B1 (en) | 2009-03-23 | 2018-01-17 | Merck Sharp & Dohme Corp. | P2x3, receptor antagonists for treatment of pain |
| US9238647B2 (en) | 2009-03-23 | 2016-01-19 | Merck Sharp & Dohme Corp. | P2X3 receptor antagonists for treatment of pain |
| EP2410858B1 (en) | 2009-03-23 | 2016-09-07 | Merck Sharp & Dohme Corp. | P2x3 receptor antagonists for treatment of pain |
| US9132094B2 (en) | 2009-04-01 | 2015-09-15 | Bial—Portela & Ca, S.A. | Pharmaceutical formulations comprising nitrocatechol derivatives and methods of making thereof |
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| WO2011007324A1 (en) | 2009-07-16 | 2011-01-20 | Actelion Pharmaceuticals Ltd | Pyridin-4-yl derivatives |
| EP2544688B1 (en) | 2010-03-02 | 2016-09-07 | President and Fellows of Harvard College | Methods and compositions for treatment of angelman syndrome |
| UA109804C2 (xx) | 2011-01-19 | 2015-10-12 | 2-метоксипіридин-4-ільні похідні | |
| US20140045900A1 (en) | 2011-02-11 | 2014-02-13 | Bial-Portela & Ca, S.A. | Administration regime for nitrocatechols |
| PT2791134T (pt) | 2011-12-13 | 2019-12-18 | BIAL PORTELA & Cª S A | Composto químico útil como intermediário para a preparação de um inibidor de catecol-o-metiltransferase |
| 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 |
| BR112015019643A8 (pt) * | 2013-02-15 | 2019-11-05 | Monsanto Technology Llc | compostos de 3,5-dissubstituído-4,5-di-hidro-1,2,4-oxadiazol, composição nematicida aquosa, semente e método para controlar nematódeos indesejáveis |
| 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 |
| MY192358A (en) | 2015-05-20 | 2022-08-17 | 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 |
| TWI681956B (zh) | 2015-06-23 | 2020-01-11 | 日商橘生藥品工業股份有限公司 | 吡唑衍生物或其藥理學上容許之鹽 |
| ES2975136T3 (es) * | 2016-03-30 | 2024-07-03 | Sinntaxis AB | Moduladores alost alostéricos negativos de MGLUR5 para uso en el tratamiento de daños cerebrales maduros |
| EP3904350B1 (en) * | 2018-04-12 | 2023-08-23 | Bayer Aktiengesellschaft | N-(cyclopropylmethyl)-5-(methylsulfonyl)-n-{1-[1-(pyrimidin-2-yl)-1h-1,2,4-triazol-5-yl]ethyl}benzamide derivatives and the corresponding pyridine-carboxamide derivatives as pesticides |
| KR102276327B1 (ko) * | 2019-06-25 | 2021-07-12 | 연세대학교 산학협력단 | 신규 옥사다이아졸 화합물 및 이를 포함하는 당뇨 예방 또는 치료용 조성물 |
| MX2022002597A (es) * | 2019-09-05 | 2022-05-13 | Trevena Inc | Métodos de tratamiento de la epilepsia usando los métodos. |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP3342874B2 (ja) * | 1995-04-21 | 2002-11-11 | ニューロサーチ、アクティーゼルスカブ | ベンズイミダゾール化合物、およびｇａｂａａレセプター複合体モジュレーターとしてのその使用 |
| 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 |
| CA2311131A1 (en) * | 1997-11-21 | 1999-06-03 | Nps Pharmaceuticals, Inc. | Metabotropic glutamate receptor antagonists for treating central nervous system diseases |
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2000
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- 2000-08-18 UA UA2002032079A patent/UA75871C2/uk unknown
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- 2000-08-18 WO PCT/US2000/022618 patent/WO2001012627A1/en not_active Ceased
- 2000-08-18 DK DK00955657T patent/DK1210344T3/da active
- 2000-08-18 NZ NZ517221A patent/NZ517221A/en not_active IP Right Cessation
- 2000-08-18 HU HU0202757A patent/HUP0202757A3/hu unknown
- 2000-08-18 AT AT00955657T patent/ATE307129T1/de active
- 2000-08-18 MX MXPA02001764A patent/MXPA02001764A/es active IP Right Grant
- 2000-08-18 JP JP2001517525A patent/JP3790472B2/ja not_active Expired - Fee Related
- 2000-08-18 CN CNB008145024A patent/CN1313465C/zh not_active Expired - Fee Related
- 2000-08-18 KR KR1020027002120A patent/KR100875222B1/ko not_active Expired - Fee Related
- 2000-08-18 EE EEP200200079A patent/EE200200079A/xx unknown
- 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 ES ES00955657T patent/ES2250177T3/es not_active Expired - Lifetime
- 2000-08-18 CA CA002381975A patent/CA2381975A1/en not_active Abandoned
- 2000-08-18 SK SK251-2002A patent/SK2512002A3/sk unknown
- 2000-08-18 RU RU2002107201/04A patent/RU2296127C9/ru not_active IP Right Cessation
- 2000-08-18 CZ CZ2002599A patent/CZ2002599A3/cs unknown
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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
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2006
- 2006-01-25 JP JP2006016914A patent/JP2006143746A/ja active Pending
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