CA2331735A1 - Phenylurea and phenylthio urea derivatives - Google Patents
Phenylurea and phenylthio urea derivatives Download PDFInfo
- Publication number
- CA2331735A1 CA2331735A1 CA002331735A CA2331735A CA2331735A1 CA 2331735 A1 CA2331735 A1 CA 2331735A1 CA 002331735 A CA002331735 A CA 002331735A CA 2331735 A CA2331735 A CA 2331735A CA 2331735 A1 CA2331735 A1 CA 2331735A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- naphthyridine
- compound
- alkyl
- pharmaceutically acceptable
- 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.)
- Abandoned
Links
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 title abstract description 11
- FULZLIGZKMKICU-UHFFFAOYSA-N N-phenylthiourea Chemical class NC(=S)NC1=CC=CC=C1 FULZLIGZKMKICU-UHFFFAOYSA-N 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 101
- 229910052739 hydrogen Inorganic materials 0.000 claims description 84
- 150000003839 salts Chemical class 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 239000005557 antagonist Substances 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 102000008834 Orexin receptor Human genes 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 208000035475 disorder Diseases 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 101000598921 Homo sapiens Orexin Proteins 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 239000005864 Sulphur Substances 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- KFAJXZVDBVRZRC-UHFFFAOYSA-N 1,5-naphthyridin-4-amine Chemical compound C1=CN=C2C(N)=CC=NC2=C1 KFAJXZVDBVRZRC-UHFFFAOYSA-N 0.000 claims description 2
- JECKUINVSSXFNR-UHFFFAOYSA-N 4-chloro-1,5-naphthyridine Chemical compound C1=CN=C2C(Cl)=CC=NC2=C1 JECKUINVSSXFNR-UHFFFAOYSA-N 0.000 claims description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
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- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- XQOHGKZCTXPHMB-UHFFFAOYSA-N 1,6-naphthyridin-4-amine Chemical compound C1=NC=C2C(N)=CC=NC2=C1 XQOHGKZCTXPHMB-UHFFFAOYSA-N 0.000 claims 1
- PSSPSOSBJIWVGU-UHFFFAOYSA-N 2,8-dichloro-1,5-naphthyridine Chemical compound N1=CC=C(Cl)C2=NC(Cl)=CC=C21 PSSPSOSBJIWVGU-UHFFFAOYSA-N 0.000 claims 1
- NWJHKNUMXALBDR-UHFFFAOYSA-N 3,8-dibromo-1,5-naphthyridine Chemical compound BrC1=CC=NC2=CC(Br)=CN=C21 NWJHKNUMXALBDR-UHFFFAOYSA-N 0.000 claims 1
- BMNVIIMWNOTDPE-UHFFFAOYSA-N 3,8-dichloro-1,5-naphthyridine Chemical compound ClC1=CC=NC2=CC(Cl)=CN=C21 BMNVIIMWNOTDPE-UHFFFAOYSA-N 0.000 claims 1
- FFMPVGXKIJZSQL-UHFFFAOYSA-N 4,5-dichloro-1,6-naphthyridine Chemical compound C1=NC(Cl)=C2C(Cl)=CC=NC2=C1 FFMPVGXKIJZSQL-UHFFFAOYSA-N 0.000 claims 1
- DOHYGSCQVQSGBI-UHFFFAOYSA-N 4,8-dibromo-1,6-naphthyridine Chemical compound C1=NC=C2C(Br)=CC=NC2=C1Br DOHYGSCQVQSGBI-UHFFFAOYSA-N 0.000 claims 1
- SQLGCTFYLAMNAC-UHFFFAOYSA-N 4,8-dichloro-1,5-naphthyridine Chemical compound C1=CN=C2C(Cl)=CC=NC2=C1Cl SQLGCTFYLAMNAC-UHFFFAOYSA-N 0.000 claims 1
- RUZMWDKSPLIZSY-UHFFFAOYSA-N 4-bromo-1,5-naphthyridine Chemical compound C1=CN=C2C(Br)=CC=NC2=C1 RUZMWDKSPLIZSY-UHFFFAOYSA-N 0.000 claims 1
- IQPRTBZXSSEENH-UHFFFAOYSA-N 4-bromo-1,6-naphthyridine Chemical compound C1=NC=C2C(Br)=CC=NC2=C1 IQPRTBZXSSEENH-UHFFFAOYSA-N 0.000 claims 1
- GKEOOUFCVWEWHA-UHFFFAOYSA-N 4-chloro-1,6-naphthyridine Chemical compound C1=NC=C2C(Cl)=CC=NC2=C1 GKEOOUFCVWEWHA-UHFFFAOYSA-N 0.000 claims 1
- GQUGYKURRVQYGU-UHFFFAOYSA-N 4-iodo-1,5-naphthyridine Chemical compound C1=CN=C2C(I)=CC=NC2=C1 GQUGYKURRVQYGU-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 5
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 210000004027 cell Anatomy 0.000 description 18
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- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 239000003446 ligand Substances 0.000 description 10
- 125000001424 substituent group Chemical group 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
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- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 5
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- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- 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
- A61P3/04—Anorexiants; Antiobesity agents
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Anesthesiology (AREA)
- Child & Adolescent Psychology (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9809972.4 | 1998-05-08 | ||
| GB9809988.0 | 1998-05-08 | ||
| GBGB9809972.4A GB9809972D0 (en) | 1998-05-08 | 1998-05-08 | Compounds |
| GBGB9809988.0A GB9809988D0 (en) | 1998-05-08 | 1998-05-08 | Compounds |
| GBGB9903268.2A GB9903268D0 (en) | 1999-02-12 | 1999-02-12 | Compounds |
| GB9903268.2 | 1999-02-12 | ||
| PCT/EP1999/003100 WO1999058533A1 (en) | 1998-05-08 | 1999-05-04 | Phenylurea and phenylthio urea derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2331735A1 true CA2331735A1 (en) | 1999-11-18 |
Family
ID=27269308
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002331735A Abandoned CA2331735A1 (en) | 1998-05-08 | 1999-05-04 | Phenylurea and phenylthio urea derivatives |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6372757B1 (enExample) |
| EP (1) | EP1075478B1 (enExample) |
| JP (1) | JP4633925B2 (enExample) |
| AU (1) | AU4037799A (enExample) |
| CA (1) | CA2331735A1 (enExample) |
| DE (1) | DE69906960T2 (enExample) |
| ES (1) | ES2196806T3 (enExample) |
| WO (1) | WO1999058533A1 (enExample) |
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| US6093820A (en) | 1997-10-02 | 2000-07-25 | Taro Pharmaceutical Industries Ltd. | Method and reagents for N-alkylating ureides |
| WO2000047576A1 (en) * | 1999-02-12 | 2000-08-17 | Smithkline Beecham Plc | Cinnamide derivatives as orexin-1 receptors antagonists |
| JP2002536447A (ja) * | 1999-02-12 | 2002-10-29 | スミスクライン・ビーチャム・パブリック・リミテッド・カンパニー | フェニル尿素およびフェニルチオ尿素誘導体 |
| AU2548400A (en) | 1999-02-12 | 2000-08-29 | Smithkline Beecham Plc | Novel use of orexin receptor antagonists |
| AU6011301A (en) * | 2000-03-14 | 2001-09-24 | Actelion Pharmaceuticals Ltd | 1,2,3,4-tetrahydroisoquinoline derivatives |
| CA2408343A1 (en) | 2000-05-11 | 2002-11-07 | Banyu Pharmaceutical Co., Ltd. | N-acyltetrahydroisoquinoline derivatives |
| AU2001272476A1 (en) | 2000-06-16 | 2001-12-24 | Smithkline Beecham Plc | Piperidines for use as orexin receptor antagonists |
| US6756379B2 (en) | 2001-07-26 | 2004-06-29 | Taro Pharmaceutical Industries Ltd. | Non-sedating barbiturate compounds as neuroprotective agents |
| US7683071B2 (en) * | 2000-07-26 | 2010-03-23 | Taro Pharmaceuticals Industries Ltd. | Composition and method for improved bioavailability and enhanced brain delivery of 5,5-diphenyl barbituric acid |
| US6939873B2 (en) * | 2000-07-26 | 2005-09-06 | Taro Pharmaceuticals Industries Limited | Non-sedating barbituric acid derivatives |
| CZ20032990A3 (cs) | 2001-05-05 | 2004-04-14 | Smithkline Beecham P. L. C. | N-aroylové cyklické aminy |
| GB0115862D0 (en) | 2001-06-28 | 2001-08-22 | Smithkline Beecham Plc | Compounds |
| GB0130335D0 (en) * | 2001-12-19 | 2002-02-06 | Smithkline Beecham Plc | Compounds |
| MXPA04002269A (es) | 2002-07-09 | 2004-06-29 | Actelion Pharmaceuticals Ltd | Derivados de 7,8,9,10-tetrahidro-6h-azepino,6,7,8,9-tetrahidro-pirido y 2,3-dihidro-2h-pirrolo[2,1-b]-quinazolinona. |
| BR0315115A (pt) | 2002-10-11 | 2005-08-16 | Actelion Pharmaceuticals Ltd | Compostos, composições farmacêuticas, método para tratar ou prevenir doenças ou distúrbios em que se requer um antagonista de receptores de orexina humana, processo para a fabricação de composições farmacêuticas, e, uso de um ou mais compostos em combinação com outros compostos farmacologicamente ativos |
| CL2003002588A1 (es) * | 2002-12-11 | 2005-01-07 | Taro Pharmaceuticals Ireland L | Uso de una composicion farmaceutica que comprende acido n,n-dimetoximetildifenil barbiturico, acido n-metoximetildifenil barbiturico o acido difenil barbiturico o una sal farmaceuticamente aceptable del mismo para preparar un medicamento util en el t |
| ES2297413T3 (es) | 2003-04-28 | 2008-05-01 | Actelion Pharmaceuticals Ltd. | Derivados de quinoxalinona-3-ona utilizados como antagonistas del receptor de orexina. |
| US20050032794A1 (en) * | 2003-08-05 | 2005-02-10 | Padia Janak K. | Diamine derivatives of quinone and uses thereof |
| HUP0304101A3 (en) * | 2003-12-22 | 2008-10-28 | Sanofi Aventis | Pyrazole derivatives, process for producing them, their use, pharmaceutical compositions containing them and their intermediates |
| JP4094050B2 (ja) | 2004-03-01 | 2008-06-04 | アクテリオン ファーマシューティカルズ リミテッド | 置換１，２，３，４−テトラヒドロイソキノリン誘導体 |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| EP1781624A4 (en) * | 2004-07-02 | 2010-06-23 | Taro Pharma Ind | PROCESS FOR THE PREPARATION OF 1-METHOXYMETHYL-5,5-DIPHENYLBARBITURIC ACID |
| WO2006081522A2 (en) * | 2005-01-26 | 2006-08-03 | The Regents Of The Unversity Of California | Modulation of nmda receptor currents via orexin receptor and/or crf receptor |
| US7501395B2 (en) | 2005-04-25 | 2009-03-10 | Eisai R & D Management Co., Ltd. | Method of screening for antianxiety drugs |
| US7547782B2 (en) | 2005-09-30 | 2009-06-16 | Bristol-Myers Squibb Company | Met kinase inhibitors |
| EP2049110B1 (en) | 2006-07-14 | 2014-08-20 | Merck Sharp & Dohme Corp. | Bridged diazepan orexin receptor antagonists |
| WO2008066704A2 (en) * | 2006-11-14 | 2008-06-05 | Taro Pharmaceuticals North America, Inc. | Method of improving bioavailability for non-sedating barbiturates |
| PE20081229A1 (es) | 2006-12-01 | 2008-08-28 | Merck & Co Inc | Antagonistas de receptor de orexina de diazepam sustituido |
| CL2008001003A1 (es) | 2007-04-11 | 2008-10-17 | Actelion Pharmaceuticals Ltd | Compuestos derivados de oxazolidinona; composicion farmaceutica que comprende a dichos compuestos; y su uso para preparar un medicamento para tratar una infeccion bacteriana. |
| JP2010527924A (ja) | 2007-05-18 | 2010-08-19 | メルク・シャープ・エンド・ドーム・コーポレイション | オキソ架橋ジアゼパンオレキシン受容体アンタゴニスト |
| US8030495B2 (en) | 2007-05-23 | 2011-10-04 | Coleman Paul J | Cyclopropyl pyrrolidine orexin receptor antagonists |
| WO2008147518A1 (en) | 2007-05-23 | 2008-12-04 | Merck & Co., Inc. | Pyridyl piperidine orexin receptor antagonists |
| CN102015645B (zh) * | 2008-04-30 | 2012-11-14 | 埃科特莱茵药品有限公司 | 哌啶和吡咯烷化合物 |
| TW201031407A (en) | 2008-12-02 | 2010-09-01 | Glaxo Group Ltd | Novel compounds |
| GB0823467D0 (en) | 2008-12-23 | 2009-01-28 | Glaxo Group Ltd | Novel Compounds |
| US20120040991A1 (en) | 2009-04-24 | 2012-02-16 | Glaxo Group Limited | 3-azabicyclo [4.1.0] heptanes used as orexin antagonists |
| WO2011023585A1 (en) | 2009-08-24 | 2011-03-03 | Glaxo Group Limited | Piperidine derivatives used as orexin antagonists |
| US20120149723A1 (en) | 2009-08-24 | 2012-06-14 | Romano Di Fabio | 5-methyl-piperidine derivatives as orexin receptor antagonists for the treatment of sleep disorder |
| WO2011031745A1 (en) | 2009-09-09 | 2011-03-17 | Achaogen, Inc. | Antibacterial fluoroquinolone analogs |
| EP2332939A1 (en) | 2009-11-26 | 2011-06-15 | Æterna Zentaris GmbH | Novel Naphthyridine derivatives and the use thereof as kinase inhibitors |
| WO2012089606A1 (en) | 2010-12-28 | 2012-07-05 | Glaxo Group Limited | Azabicyclo [4.1.0] hept - 4 - yl derivatives as human orexin receptor antagonists |
| WO2012089607A1 (en) | 2010-12-28 | 2012-07-05 | Glaxo Group Limited | Novel compounds with a 3a-azabicyclo [4.1.0] heptane core acting on orexin receptors |
| AR088352A1 (es) | 2011-10-19 | 2014-05-28 | Merck Sharp & Dohme | Antagonistas del receptor de 2-piridiloxi-4-nitrilo orexina |
| WO2013119639A1 (en) | 2012-02-07 | 2013-08-15 | Eolas Therapeutics, Inc. | Substituted prolines / piperidines as orexin receptor antagonists |
| US9440982B2 (en) | 2012-02-07 | 2016-09-13 | Eolas Therapeutics, Inc. | Substituted prolines/piperidines as orexin receptor antagonists |
| TW201613902A (en) | 2014-08-13 | 2016-04-16 | Eolas Therapeutics Inc | Difluoropyrrolidines as orexin receptor modulators |
| LT3414241T (lt) | 2016-02-12 | 2022-08-25 | Astrazeneca Ab | Halogenu pakeisti piperidinai kaip oreksino receptoriaus moduliatoriai |
| AU2020286381C1 (en) | 2019-06-04 | 2025-07-10 | Hager Biosciences, Llc | Imidazolo derivatives, compositions and methods as orexin antagonists |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0222839A4 (en) * | 1985-05-17 | 1988-11-09 | Univ Australian | ANTI-MALARIA COMPOUNDS. |
| JPH05213884A (ja) * | 1991-06-14 | 1993-08-24 | Upjohn Co:The | 新規な４−アミノキノリン類およびこれを有効成分とする高血圧・鬱血性心不全の予防・治療剤 |
| CA2222687A1 (en) | 1995-05-31 | 1996-12-05 | Masami Muraoka | Novel naphthyridine derivatives |
| TR199802386T2 (xx) | 1996-05-20 | 1999-02-22 | Darwin Discovery Limited | Benzofuran karboksamidler ve bunlar�n terap�tik kullan�m�. |
| AR016817A1 (es) * | 1997-08-14 | 2001-08-01 | Smithkline Beecham Plc | Derivados de fenilurea o feniltiourea, procedimiento para su preparacion, coleccion de compuestos, compuestos intermediarios, composicion farmaceutica,metodo de tratamiento y uso de dichos compuestos para la manufactura de un medicamento |
-
1999
- 1999-05-04 CA CA002331735A patent/CA2331735A1/en not_active Abandoned
- 1999-05-04 EP EP99923540A patent/EP1075478B1/en not_active Expired - Lifetime
- 1999-05-04 WO PCT/EP1999/003100 patent/WO1999058533A1/en not_active Ceased
- 1999-05-04 US US09/700,002 patent/US6372757B1/en not_active Expired - Fee Related
- 1999-05-04 JP JP2000548337A patent/JP4633925B2/ja not_active Expired - Fee Related
- 1999-05-04 AU AU40377/99A patent/AU4037799A/en not_active Abandoned
- 1999-05-04 DE DE69906960T patent/DE69906960T2/de not_active Expired - Lifetime
- 1999-05-04 ES ES99923540T patent/ES2196806T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES2196806T3 (es) | 2003-12-16 |
| US6372757B1 (en) | 2002-04-16 |
| WO1999058533A1 (en) | 1999-11-18 |
| EP1075478B1 (en) | 2003-04-16 |
| DE69906960D1 (en) | 2003-05-22 |
| JP4633925B2 (ja) | 2011-02-16 |
| JP2003522101A (ja) | 2003-07-22 |
| AU4037799A (en) | 1999-11-29 |
| EP1075478A1 (en) | 2001-02-14 |
| DE69906960T2 (de) | 2004-01-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |