CA2300178A1 - Phenyl urea and phenyl thiourea derivatives as hfgan72 antagonists - Google Patents
Phenyl urea and phenyl thiourea derivatives as hfgan72 antagonists Download PDFInfo
- Publication number
- CA2300178A1 CA2300178A1 CA002300178A CA2300178A CA2300178A1 CA 2300178 A1 CA2300178 A1 CA 2300178A1 CA 002300178 A CA002300178 A CA 002300178A CA 2300178 A CA2300178 A CA 2300178A CA 2300178 A1 CA2300178 A1 CA 2300178A1
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- Prior art keywords
- formula
- compound
- alkyl
- nmr
- title compound
- 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
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- 239000005557 antagonist Substances 0.000 title claims abstract description 18
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 title abstract description 12
- 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 abstract description 249
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 61
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- 239000001257 hydrogen Substances 0.000 claims abstract description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 23
- 125000003118 aryl group Chemical group 0.000 claims abstract description 23
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 22
- 150000002367 halogens Chemical class 0.000 claims abstract description 22
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 15
- 238000011282 treatment Methods 0.000 claims abstract description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 9
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000005864 Sulphur Substances 0.000 claims abstract description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 7
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 111
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 30
- 201000010099 disease Diseases 0.000 claims description 17
- 208000035475 disorder Diseases 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000011321 prophylaxis Methods 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- RUYUZWMAUJHVRI-UHFFFAOYSA-N 1-(7-chloroquinolin-4-yl)-1-(3,4,5-trimethoxyphenyl)urea Chemical compound COC1=C(OC)C(OC)=CC(N(C(N)=O)C=2C3=CC=C(Cl)C=C3N=CC=2)=C1 RUYUZWMAUJHVRI-UHFFFAOYSA-N 0.000 claims description 3
- DWPJUCYLABGAME-UHFFFAOYSA-N 1-isoquinolin-1-yl-1-(1-methylindol-5-yl)urea Chemical compound C1=CC=C2C(N(C(N)=O)C=3C=C4C=CN(C4=CC=3)C)=NC=CC2=C1 DWPJUCYLABGAME-UHFFFAOYSA-N 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- MLHQRWCAOVZRMU-UHFFFAOYSA-N 1-(4-chlorophenyl)-1-(7-chloroquinolin-4-yl)urea Chemical compound C=1C=NC2=CC(Cl)=CC=C2C=1N(C(=O)N)C1=CC=C(Cl)C=C1 MLHQRWCAOVZRMU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 2
- QIRLJMJLJXBUMP-UHFFFAOYSA-N 7-fluoroquinoline-4-carboxylic acid Chemical compound FC1=CC=C2C(C(=O)O)=CC=NC2=C1 QIRLJMJLJXBUMP-UHFFFAOYSA-N 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
- 238000004519 manufacturing process Methods 0.000 claims description 2
- XXLFLUJXWKXUGS-UHFFFAOYSA-N 6-methoxyquinoline-4-carboxylic acid Chemical compound N1=CC=C(C(O)=O)C2=CC(OC)=CC=C21 XXLFLUJXWKXUGS-UHFFFAOYSA-N 0.000 claims 2
- CTZRSKUIEVVAJG-UHFFFAOYSA-N 1-(7-chloroquinolin-4-yl)-3-(4-methoxyphenyl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)NC1=CC=NC2=CC(Cl)=CC=C12 CTZRSKUIEVVAJG-UHFFFAOYSA-N 0.000 claims 1
- RETJOGPFTCSHIR-UHFFFAOYSA-N 1-[3-chloro-4-(trifluoromethyl)phenyl]-3-(5-nitroquinolin-4-yl)urea Chemical compound C=12C([N+](=O)[O-])=CC=CC2=NC=CC=1NC(=O)NC1=CC=C(C(F)(F)F)C(Cl)=C1 RETJOGPFTCSHIR-UHFFFAOYSA-N 0.000 claims 1
- ORRPEZHMWMSQGQ-UHFFFAOYSA-N 1-[3-chloro-4-(trifluoromethyl)phenyl]-3-quinolin-4-ylurea Chemical compound C1=C(Cl)C(C(F)(F)F)=CC=C1NC(=O)NC1=CC=NC2=CC=CC=C12 ORRPEZHMWMSQGQ-UHFFFAOYSA-N 0.000 claims 1
- QEJVAJGAMCJITG-UHFFFAOYSA-N 5-chloroquinoline-4-carboxylic acid Chemical compound C1=CC(Cl)=C2C(C(=O)O)=CC=NC2=C1 QEJVAJGAMCJITG-UHFFFAOYSA-N 0.000 claims 1
- ZRYMLJGLNAOPNK-UHFFFAOYSA-N 6-chloroquinoline-4-carboxylic acid Chemical compound C1=C(Cl)C=C2C(C(=O)O)=CC=NC2=C1 ZRYMLJGLNAOPNK-UHFFFAOYSA-N 0.000 claims 1
- SUCSQKWIHAXNTM-UHFFFAOYSA-N 6-ethoxyquinoline-4-carboxylic acid Chemical compound N1=CC=C(C(O)=O)C2=CC(OCC)=CC=C21 SUCSQKWIHAXNTM-UHFFFAOYSA-N 0.000 claims 1
- TXYVRYRRTQYTHJ-UHFFFAOYSA-N 7-chloroquinoline-4-carboxylic acid Chemical compound ClC1=CC=C2C(C(=O)O)=CC=NC2=C1 TXYVRYRRTQYTHJ-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
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- 102000004877 Insulin Human genes 0.000 abstract description 4
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- 229940125396 insulin Drugs 0.000 abstract description 4
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- 230000001419 dependent effect Effects 0.000 abstract description 2
- 239000008186 active pharmaceutical agent Substances 0.000 description 124
- 238000005160 1H NMR spectroscopy Methods 0.000 description 96
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 83
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 73
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 63
- 239000000203 mixture Substances 0.000 description 61
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 60
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- 239000007787 solid Substances 0.000 description 48
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
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- 238000001914 filtration Methods 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
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- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
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Classifications
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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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
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
- A61P5/12—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH for decreasing, blocking or antagonising the activity of the posterior pituitary hormones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
- C07D215/42—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/50—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D413/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Pain & Pain Management (AREA)
- Reproductive Health (AREA)
- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Anesthesiology (AREA)
- Gynecology & Obstetrics (AREA)
- Pregnancy & Childbirth (AREA)
- Emergency Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9717178.9 | 1997-08-14 | ||
| GBGB9717178.9A GB9717178D0 (en) | 1997-08-14 | 1997-08-14 | Compounds |
| GB9807756.3 | 1998-04-08 | ||
| GBGB9807756.3A GB9807756D0 (en) | 1998-04-08 | 1998-04-08 | Compounds |
| PCT/GB1998/002437 WO1999009024A1 (en) | 1997-08-14 | 1998-08-13 | Phenyl urea and phenyl thiourea derivatives as hfgan72 antagonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2300178A1 true CA2300178A1 (en) | 1999-02-25 |
Family
ID=26312063
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002300178A Abandoned CA2300178A1 (en) | 1997-08-14 | 1998-08-13 | Phenyl urea and phenyl thiourea derivatives as hfgan72 antagonists |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US6410529B1 (enExample) |
| EP (1) | EP1003737A1 (enExample) |
| JP (1) | JP2001515075A (enExample) |
| AR (1) | AR016817A1 (enExample) |
| AU (1) | AU8741198A (enExample) |
| CA (1) | CA2300178A1 (enExample) |
| WO (1) | WO1999009024A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2263479A1 (en) | 1996-09-25 | 1998-04-02 | Zeneca Limited | Quinoline derivatives inhibiting the effect of growth factors such as vegf |
| GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
| US5935814A (en) * | 1997-04-30 | 1999-08-10 | Smithkline Beecham Corporation | Polynucleotides encoding HFGAN72Y receptor |
| US6020157A (en) * | 1997-04-30 | 2000-02-01 | Smithkline Beecham Corporation | Polynucleotides encoding HFGAN72X receptor |
| US6653086B1 (en) | 1998-04-14 | 2003-11-25 | Arena Pharmaceuticals, Inc. | Endogenous constitutively activated G protein-coupled orphan receptors |
| WO1999058533A1 (en) * | 1998-05-08 | 1999-11-18 | Smithkline Beecham Plc | Phenylurea and phenylthio urea derivatives |
| US6420563B1 (en) | 1998-07-31 | 2002-07-16 | Arena Pharmaceuticals, Inc. | Small molecule modulators of G protein-coupled receptor six |
| AU1689600A (en) * | 1998-12-22 | 2000-07-12 | Mitsubishi Chemical Corporation | Amide derivatives |
| WO2000047577A1 (en) * | 1999-02-12 | 2000-08-17 | Smithkline Beecham Plc | Phenyl urea and phenyl thiourea derivatives as orexin receptor antagonists |
| US6596730B1 (en) | 1999-02-12 | 2003-07-22 | Smithkline Beecham P.L.C. | Phenyl urea and phenyl thiourea derivatives |
| WO2000047576A1 (en) * | 1999-02-12 | 2000-08-17 | Smithkline Beecham Plc | Cinnamide derivatives as orexin-1 receptors antagonists |
| ATE241345T1 (de) * | 1999-02-12 | 2003-06-15 | Smithkline Beecham Plc | Neue verwendung von orexinrezeptorantagonisten |
| CN1364167A (zh) * | 1999-02-26 | 2002-08-14 | 阿瑞那制药公司 | G蛋白偶联受体6的小分子调节剂 |
| ES2292461T3 (es) * | 1999-07-07 | 2008-03-16 | Astrazeneca Uk Limited | Derivados de quinazolina. |
| US6764858B2 (en) | 1999-09-29 | 2004-07-20 | Pharmacia & Upjohn Company | Methods for creating a compound library |
| WO2001023330A2 (en) * | 1999-09-29 | 2001-04-05 | Pharmacia & Upjohn Company | Methods for creating a compound library and identifying lead chemical templates and ligands for target molecules |
| US6677160B1 (en) | 1999-09-29 | 2004-01-13 | Pharmacia & Upjohn Company | Methods for creating a compound library and identifying lead chemical templates and ligands for target molecules |
| JP3522727B2 (ja) | 1999-11-05 | 2004-04-26 | アストラゼネカ アクチボラグ | Vegf阻害剤としてのキナゾリン誘導体 |
| AU2001235804A1 (en) | 2000-03-06 | 2001-09-17 | Astrazeneca Ab | Therapy |
| PT1274687E (pt) | 2000-03-14 | 2005-04-29 | Actelion Pharmaceuticals Ltd | Derivados de 1,2,3,4-tetra-hidroisoquinolina |
| DE60121931T2 (de) | 2000-04-07 | 2007-03-01 | Astrazeneca Ab | Chinazolinverbindungen |
| CA2408343A1 (en) | 2000-05-11 | 2002-11-07 | Banyu Pharmaceutical Co., Ltd. | N-acyltetrahydroisoquinoline derivatives |
| DE60110066T2 (de) * | 2000-06-16 | 2006-02-02 | Smithkline Beecham P.L.C., Brentford | Piperidine zur verwendung als orexinrezeptorantagonisten |
| WO2002000644A1 (en) | 2000-06-24 | 2002-01-03 | Astrazeneca Ab | Guanidine derivatives of quinazoline and quinoline for use in the treatment of autoimmune diseases |
| AU2002216758A1 (en) * | 2000-07-03 | 2002-01-14 | Astrazeneca Ab | Quinazolines with therapeutic use |
| WO2002049648A1 (en) | 2000-12-21 | 2002-06-27 | Schering Corporation | Heteroaryl urea neuropeptide y y5 receptor antagonists |
| US6946476B2 (en) | 2000-12-21 | 2005-09-20 | Schering Corporation | Heteroaryl urea neuropeptide Y Y5 receptor antagonists |
| ES2299567T3 (es) | 2001-05-05 | 2008-06-01 | Smithkline Beecham Plc | N-aroilaminas ciclicas. |
| GB0115862D0 (en) * | 2001-06-28 | 2001-08-22 | Smithkline Beecham Plc | Compounds |
| WO2003002561A1 (en) | 2001-06-28 | 2003-01-09 | Smithkline Beecham P.L.C. | N-aroyl cyclic amine derivatives as orexin receptor antagonists |
| NZ538029A (en) | 2002-07-09 | 2006-08-31 | Actelion Pharmaceuticals Ltd | 7,8,9,10-tetrahydro-6H-azepino, 6,7,8,9-tetrahydro-pyrido and 2,3-dihydro-2H-pyrrolo[2,1-b]-quinazolinone derivatives |
| BR0314353A (pt) * | 2002-09-17 | 2005-07-19 | Actelion Pharmaceuticals Ltd | Compostos, composições farmacêuticas, uso de um ou mais compostos em combinação com outros compostos farmacologicamente ativos, e, método para tratar um paciente que sofre de um distúrbio |
| JP4528125B2 (ja) | 2002-10-11 | 2010-08-18 | アクテリオン ファーマシューティカルズ リミテッド | スルホニルアミノ−酢酸誘導体 |
| GB0230195D0 (en) * | 2002-12-24 | 2003-02-05 | Biofocus Plc | Compound Libraries |
| AU2003295158A1 (en) * | 2002-12-24 | 2004-07-22 | Biofocus Plc | Compound libraries of 1,3,5-substitute indazole derivatives as compounds for targetting compounds capable of binding to the g-protein coupled receptor |
| MXPA05010496A (es) * | 2003-03-28 | 2005-11-16 | Pharmacia & Upjohn Co Llc | Moduladores alostericos positivos del receptor de acetilcolina nicotinico. |
| WO2004089296A2 (en) | 2003-04-03 | 2004-10-21 | The Regents Of The University Of California | Improved inhibitors for the soluble epoxide hydrolase |
| EP1631546A1 (en) * | 2003-04-25 | 2006-03-08 | H. Lundbeck A/S | Sustituted indoline and indole derivatives |
| JP2007523846A (ja) | 2003-04-28 | 2007-08-23 | アクテリオン ファマシューティカルズ リミテッド | キノキサリノン誘導体 |
| KR100848747B1 (ko) | 2004-03-01 | 2008-07-25 | 액테리온 파마슈티칼 리미티드 | 치환된 1,2,3,4-테트라하이드로이소퀴놀린 유도체 |
| CA2559665A1 (en) | 2004-03-16 | 2005-09-29 | The Regents Of The University Of California | Reducing nephropathy with inhibitors of soluble epoxide hydrolase and epoxyeicosanoids |
| US20080125403A1 (en) | 2004-04-02 | 2008-05-29 | Merck & Co., Inc. | Method of Treating Men with Metabolic and Anthropometric Disorders |
| US7550499B2 (en) * | 2004-05-12 | 2009-06-23 | Bristol-Myers Squibb Company | Urea antagonists of P2Y1 receptor useful in the treatment of thrombotic conditions |
| WO2006040056A1 (en) * | 2004-10-13 | 2006-04-20 | Merck Patent Gmbh | Heterocyclic substituted bisarylurea derivatives as kinase inhibitors |
| NZ554555A (en) | 2004-10-20 | 2011-09-30 | Univ California | Cyclohexyl-urea derivatives as improved inhibitors for the soluble epoxide hydrolase |
| US7501395B2 (en) | 2005-04-25 | 2009-03-10 | Eisai R & D Management Co., Ltd. | Method of screening for antianxiety drugs |
| AR059826A1 (es) | 2006-03-13 | 2008-04-30 | Univ California | Inhibidores de urea conformacionalmente restringidos de epoxido hidrolasa soluble |
| AU2007272854B2 (en) | 2006-07-14 | 2013-08-01 | Merck Sharp & Dohme Corp. | Bridged diazepan orexin receptor antagonists |
| PE20081229A1 (es) | 2006-12-01 | 2008-08-28 | Merck & Co Inc | Antagonistas de receptor de orexina de diazepam sustituido |
| WO2008101030A1 (en) * | 2007-02-13 | 2008-08-21 | The Regents Of The University Of California | Methods for amplifying steroid hormone effects |
| AU2008255005B2 (en) | 2007-05-18 | 2013-05-02 | Merck Sharp & Dohme Corp. | OXO bridged diazepan orexin receptor antagonists |
| WO2008150364A1 (en) | 2007-05-23 | 2008-12-11 | Merck & Co., Inc. | Cyclopropyl pyrrolidine orexin receptor antagonists |
| HRP20120240T1 (hr) | 2007-05-23 | 2012-04-30 | Merck Sharp & Dohme Corp. | Piridil piperidin antagonisti receptora za oreksin |
| KR20100135962A (ko) * | 2008-04-30 | 2010-12-27 | 액테리온 파마슈티칼 리미티드 | 피페리딘 및 피롤리딘 화합물 |
| AR074426A1 (es) | 2008-12-02 | 2011-01-19 | Glaxo Group Ltd | Compuesto de n-(((1s,4s,6s)-3-(2-piridinilcarbonil)3-azabiciclo (4,1.0)hept-4-il) metil)-2-heteroarilamina, su uso para la prepracion de un medicamento para el tratamiento de una enfermedad que requiere un antagonista de un receptor de orexina humana y composicion farmaceutica que lo comprende |
| GB0823467D0 (en) | 2008-12-23 | 2009-01-28 | Glaxo Group Ltd | Novel Compounds |
| EP2396307B1 (en) * | 2009-02-11 | 2014-10-15 | Merck Patent GmbH | Novel amino azaheterocyclic carboxamides |
| KR20120007061A (ko) | 2009-04-24 | 2012-01-19 | 글락소 그룹 리미티드 | 오렉신 길항제로서 사용되는 3-아자비시클로[4.1.0]헵탄 |
| JP2013502448A (ja) | 2009-08-24 | 2013-01-24 | グラクソ グループ リミテッド | オレキシンアンタゴニストとして用いられるピペリジン誘導体 |
| WO2011023578A1 (en) | 2009-08-24 | 2011-03-03 | Glaxo Group Limited | 5-methyl-piperidine derivatives as orexin receptor antagonists for the treatment of sleep disorder |
| US9452980B2 (en) | 2009-12-22 | 2016-09-27 | Hoffmann-La Roche Inc. | Substituted benzamides |
| WO2012054093A2 (en) | 2010-01-29 | 2012-04-26 | The Regents Of The University Of California | Acyl piperidine inhibitors of soluble epoxide hydrolase |
| PE20130211A1 (es) | 2010-04-02 | 2013-03-22 | Senomyx Inc | Modificador del sabor dulce |
| CA2803387C (en) * | 2010-07-29 | 2017-12-05 | Bayard R. Huck | Cyclic amine azaheterocyclic carboxamides |
| UA110113C2 (xx) * | 2010-07-29 | 2015-11-25 | Біциклічні азагетероциклічні карбоксаміди | |
| 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 |
| CA2841012C (en) | 2011-08-12 | 2019-07-30 | Senomyx, Inc. | Sweet flavor modifier |
| AR088352A1 (es) | 2011-10-19 | 2014-05-28 | Merck Sharp & Dohme | Antagonistas del receptor de 2-piridiloxi-4-nitrilo orexina |
| WO2016073251A1 (en) | 2014-11-07 | 2016-05-12 | Senomyx, Inc. | Substituted 4-amino-5-(cyclohexyloxy)quinoline-3-carboxylic acids as sweet flavor modifiers |
| CN108713019B (zh) | 2016-03-17 | 2021-06-15 | 豪夫迈·罗氏有限公司 | 具有作为taar的激动剂的活性的5-乙基-4-甲基-吡唑-3-甲酰胺衍生物 |
| EP3937919A4 (en) | 2019-03-14 | 2023-04-12 | Board of Regents, The University of Texas System | SMALL MOLECULES GRB2 STABILIZER FOR INHIBITION OF RAS-MAP KINASE |
| WO2021161230A1 (en) * | 2020-02-12 | 2021-08-19 | Curadev Pharma Pvt. Ltd. | Small molecule sting antagonists |
| WO2025067473A1 (zh) * | 2023-09-28 | 2025-04-03 | 四川大学华西医院 | 一种含苯环的具有镇痛功效的化合物及其制备方法和用途 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4009020A (en) * | 1975-05-06 | 1977-02-22 | Amchem Products, Inc. | Method of regulating plant growth |
| US5552411A (en) * | 1995-05-26 | 1996-09-03 | Warner-Lambert Company | Sulfonylquinolines as central nervous system and cardiovascular agents |
| US5731315A (en) | 1995-06-07 | 1998-03-24 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Substituted sulfonic acid n- (aminoiminomethyl)phenylalkyl!-azaheterocyclamide compounds |
| CN1244798A (zh) * | 1996-12-13 | 2000-02-16 | 罗纳·布朗克罗尔药制品有限公司 | 磺酸或磺酰氨基n-(杂芳烷基)-氮杂环酰胺化合物 |
-
1998
- 1998-08-12 AR ARP980104002A patent/AR016817A1/es unknown
- 1998-08-13 US US09/485,623 patent/US6410529B1/en not_active Expired - Fee Related
- 1998-08-13 WO PCT/GB1998/002437 patent/WO1999009024A1/en not_active Ceased
- 1998-08-13 JP JP2000509705A patent/JP2001515075A/ja not_active Withdrawn
- 1998-08-13 AU AU87411/98A patent/AU8741198A/en not_active Abandoned
- 1998-08-13 CA CA002300178A patent/CA2300178A1/en not_active Abandoned
- 1998-08-13 EP EP98938812A patent/EP1003737A1/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| WO1999009024A1 (en) | 1999-02-25 |
| JP2001515075A (ja) | 2001-09-18 |
| AR016817A1 (es) | 2001-08-01 |
| EP1003737A1 (en) | 2000-05-31 |
| US6410529B1 (en) | 2002-06-25 |
| AU8741198A (en) | 1999-03-08 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| FZDE | Dead |