WO1995011243A1 - Benzanilide derivatives as 5ht-1d receptor antagonists - Google Patents
Benzanilide derivatives as 5ht-1d receptor antagonists Download PDFInfo
- Publication number
- WO1995011243A1 WO1995011243A1 PCT/EP1994/003387 EP9403387W WO9511243A1 WO 1995011243 A1 WO1995011243 A1 WO 1995011243A1 EP 9403387 W EP9403387 W EP 9403387W WO 9511243 A1 WO9511243 A1 WO 9511243A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- formula
- methyl
- compound
- dihydro
- methylpiperazin
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- 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
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/18—Ethylenedioxybenzenes, not substituted on the hetero ring
-
- 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
- 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
Definitions
- the group R can also be an optionally substituted phenyl group, in particular a phenyl group disubstituted by Ci.galkyl and an optionally substituted 5 to 7-membered heterocyclic ring containing 1 to 3 heteroatoms selected from oxygen, nitrogen or sulphur.
- Preferred 5 to 7-membered heterocyclic rings include those listed above.
- Preferred substituents for such rings include Ci.galkyl, in particular methyl.
- R 3 is as defined in formula (I) and Hal is halogen, or
- the present invention also provides a compound of general formula (I) or a physiologically acceptable salt or solvate thereof for use in the treatment of the aforementioned disorders.
- the present invention also provides a pharmaceutical composition, which comprises a compound of formula (I) or a pharmaceutically acceptable salt thereof, and a
- fluid unit dosage forms are prepared utilising a compound of the invention or pharmaceutically acceptable salt thereof and a sterile vehicle.
- the compound depending on the vehicle and concentration used, can be either suspended or dissolved in the vehicle.
- the compound can be dissolved for injection and filter sterilised before filling into a suitable vial or ampoule and sealing.
- adjuvants such as a local anaesthetic, preservatives and buffering agents are dissolved in the vehicle.
- the composition can be frozen after filling into the vial and the water removed under vacuum.
- Parenteral suspensions are prepared in substantially the same manner, except that the compound is suspended in the vehicle instead of being dissolved, and sterilisation cannot be accomplished by filtration.
- the compound can be sterilised by exposure to ethylene oxide before suspension in a sterile vehicle.
- a surfactant or wetting agent is included in the composition to facilitate uniform distribution of the compound.
- Benzodioxan-5-carboxylic acid (prepared as described by E.A.Watts, in Azabicycloalkylbenzamides and pharmaceutical compositions containing them, EP 82-303057 June 1982) (15 g) was dissolved in a mixture of glacial acetic acid (67 ml) and acetic anhydride (67 ml). The solution was heated to 40° C and treated with a solution of fuming nitric acid (13 ml) in acetic acid (13 ml) at a rate such that the temperature was maintained at 45-50° C with occasional ice/water cooling. The mixture was stirred at 50°-53° C for 2 days, then cooled and filtered to give the title compound as a white powder (4.09 g, 22%).
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP94930171A EP0724580A1 (en) | 1993-10-19 | 1994-10-13 | Benzanilide derivatives as 5ht-1d receptor antagonists |
JP7511300A JPH09503773A (en) | 1993-10-19 | 1994-10-13 | Benzanilide derivative for 5HT-1D receptor antagonist |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB939321490A GB9321490D0 (en) | 1993-10-19 | 1993-10-19 | Novel compounds |
GB9325866.3 | 1993-12-17 | ||
GB939325866A GB9325866D0 (en) | 1993-12-17 | 1993-12-17 | Novel compounds |
GB9321490.6 | 1993-12-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1995011243A1 true WO1995011243A1 (en) | 1995-04-27 |
Family
ID=26303698
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1994/003387 WO1995011243A1 (en) | 1993-10-19 | 1994-10-13 | Benzanilide derivatives as 5ht-1d receptor antagonists |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP0724580A1 (en) |
JP (1) | JPH09503773A (en) |
WO (1) | WO1995011243A1 (en) |
Cited By (31)
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---|---|---|---|---|
WO1998027081A1 (en) * | 1996-12-19 | 1998-06-25 | Smithkline Beecham Plc | Sulphonamide derivatives, process for their preparation, and their use as medicaments |
WO1998027058A2 (en) * | 1996-12-19 | 1998-06-25 | Smithkline Beecham Plc | N-piperazin-1-ylphenyl-benzamide derivatives |
US6107328A (en) * | 1995-09-18 | 2000-08-22 | Smithkline Beecham P.L.C. | Use of 5HT1B receptor antagonist for the treatment of vascular disease |
US6124283A (en) * | 1996-03-22 | 2000-09-26 | Astra Aktiebolag | Substituted 1,2,3,4-tetrahydronaphthalene derivatives |
WO2001009123A1 (en) * | 1999-07-29 | 2001-02-08 | Eli Lilly And Company | Benzofurylpiperazine serotonin agonists |
WO2001009111A1 (en) * | 1999-07-29 | 2001-02-08 | Eli Lilly And Company | Benzofurylpiperazines and benzofurylhomopiperazines: serotonin agonists |
US6291458B1 (en) | 1997-07-02 | 2001-09-18 | Astrazeneca Ab | Morpholinobenzamide salts |
US6313118B1 (en) | 1997-07-25 | 2001-11-06 | Astra Aktiebolag | Substituted 1,2,3,4-tetrahydronaphthalene derivatives |
US6858592B2 (en) | 2001-06-29 | 2005-02-22 | Genzyme Corporation | Aryl boronic acids for treating obesity |
US7041280B2 (en) | 2001-06-29 | 2006-05-09 | Genzyme Corporation | Aryl boronate functionalized polymers for treating obesity |
WO2006062481A1 (en) * | 2004-12-09 | 2006-06-15 | Biovitrum Ab | New benzofuran derivatives and their use in the treatment of obesity, type ii diabetes and cns disorders . |
US7125898B2 (en) | 2002-02-12 | 2006-10-24 | Smithkline Beecham Corporation | Nicotinamide derivatives useful as p38 inhibitors. |
US7151118B2 (en) | 2001-10-17 | 2006-12-19 | Glaxo Group Limited | Biphenylcarboxylic amide derivatives as p38-kinase inhibitors |
US7166597B2 (en) | 2000-08-22 | 2007-01-23 | Glaxo Group Limited | Fused pyrazole derivatives being protein kinase inhibitors |
US7166623B2 (en) | 2001-10-17 | 2007-01-23 | Glaxo Group Limited | 2′-Methyl-5′-(1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxamide derivatives and their use as p38 kinase inhibitors |
US7183297B2 (en) | 2001-10-17 | 2007-02-27 | Glaxo Group Limited | Biphenyl-derivatives as p38-kinase inhibitors |
US7208629B2 (en) | 2001-10-17 | 2007-04-24 | Glaxo Group Limited | 5′-Carbamoyl-1,1-biphenyl-4-carboxamide derivatives and their use as p38 kinase inhibitors |
US7271289B2 (en) | 2003-04-09 | 2007-09-18 | Smithkline Beecham Corporation | Biphenylcarboxylic amide derivatives as p38 kinase inhibitors |
US7384963B2 (en) | 2001-10-17 | 2008-06-10 | Glaxo Group Limited | 2′-Methyl-5-(1,3,4-oxadiazol-2-yl)1, 1′-biphenyl-4-carboxaide derivatives and their use as p38 kinase |
US7396843B2 (en) | 2001-10-17 | 2008-07-08 | Glaxo Group Limited | 5′-carbamoyl-1,1′-biphenyl-4-carboxamide derivatives and their use as p38 kinase inhibitors |
US7432289B2 (en) | 2001-10-17 | 2008-10-07 | Glaxo Group Limited | 5-Acylamino-1,1′-biphenyl-4-carboxamide derivatives and their use as P38 kinase inhibitors |
US7504395B2 (en) | 2001-07-20 | 2009-03-17 | Psychogenics, Inc. | Treatment for attention-deficit hyperactivity disorder |
US7572790B2 (en) | 2003-04-09 | 2009-08-11 | Smithkline Beecham Corporation | Biphenyl carboxylic amide p38 kinase inhibitors |
US7626055B2 (en) | 2003-04-09 | 2009-12-01 | Smithkline Beecham Corporation | Biphenyl-carboxamide derivatives and their use as p38 kinase inhibitors |
US7642276B2 (en) | 2002-07-31 | 2010-01-05 | Smithkline Beecham Corporation | Fused heteroaryl derivatives for use as P38 kinase inhibitors |
US7838540B2 (en) | 2003-08-11 | 2010-11-23 | Glaxosmithkline Llc | 3-aminocarbonyl, 6-phenyl substituted pyridine-1-oxides as p38 kinase inhibitors |
WO2011098776A1 (en) | 2010-02-15 | 2011-08-18 | Cambridge Enterprise Limited | 5-ht receptor modulators |
US8445686B2 (en) * | 2007-08-27 | 2013-05-21 | Abbvie Inc. | 4-(4-pyridinyl)-benzamides and their use as rock activity modulators |
WO2016028971A1 (en) * | 2014-08-21 | 2016-02-25 | Bristol-Myers Squibb Company | Tied-back benzamide derivatives as potent rock inhibitors |
WO2020183011A1 (en) | 2019-03-14 | 2020-09-17 | Institut Curie | Htr1d inhibitors and uses thereof in the treatment of cancer |
US11498903B2 (en) | 2017-08-17 | 2022-11-15 | Bristol-Myers Squibb Company | 2-(1,1′-biphenyl)-1H-benzodimidazole derivatives and related compounds as apelin and APJ agonists for treating cardiovascular diseases |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0533268A1 (en) * | 1991-09-18 | 1993-03-24 | Glaxo Group Limited | Benzanilide derivatives as 5-HT1D antagonists |
EP0533266A1 (en) * | 1991-09-18 | 1993-03-24 | Glaxo Group Limited | Benzanilide derivatives as 5-HT1D antagonists |
EP0533267A1 (en) * | 1991-09-18 | 1993-03-24 | Glaxo Group Limited | Benzanilide derivatives as 5-HT1D antagonists |
-
1994
- 1994-10-13 WO PCT/EP1994/003387 patent/WO1995011243A1/en not_active Application Discontinuation
- 1994-10-13 JP JP7511300A patent/JPH09503773A/en active Pending
- 1994-10-13 EP EP94930171A patent/EP0724580A1/en not_active Withdrawn
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0533268A1 (en) * | 1991-09-18 | 1993-03-24 | Glaxo Group Limited | Benzanilide derivatives as 5-HT1D antagonists |
EP0533266A1 (en) * | 1991-09-18 | 1993-03-24 | Glaxo Group Limited | Benzanilide derivatives as 5-HT1D antagonists |
EP0533267A1 (en) * | 1991-09-18 | 1993-03-24 | Glaxo Group Limited | Benzanilide derivatives as 5-HT1D antagonists |
Non-Patent Citations (2)
Title |
---|
B.J. VAN STEEN ET AL.: "Structure-affinity relationship studies on 5-HT1A receptor ligands. Heterobicyclic phenylpiperazines with N4-aralkyl substituents.", JOURNAL OF MEDICINAL CHEMISTRY, vol. 37, no. 17, 19 August 1994 (1994-08-19), WASHINGTON US, pages 2761 - 2773 * |
J.W. CLITHEROW ET AL.: "Evolution of a novel series of ((N,N-Dimethylamino)propyl)- and piperazinylbenzanilides as the first selective 5-HT1D antagonists.", JOURNAL OF MEDICINAL CHEMISTRY, vol. 37, no. 15, 22 July 1994 (1994-07-22), WASHINGTON US, pages 2253 - 2257 * |
Cited By (50)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6107328A (en) * | 1995-09-18 | 2000-08-22 | Smithkline Beecham P.L.C. | Use of 5HT1B receptor antagonist for the treatment of vascular disease |
US6410530B1 (en) | 1996-03-22 | 2002-06-25 | Astrazeneca Ab | Substituted 1,2,3,4-tetrahydronaphthalene derivatives |
US6124283A (en) * | 1996-03-22 | 2000-09-26 | Astra Aktiebolag | Substituted 1,2,3,4-tetrahydronaphthalene derivatives |
WO1998027081A1 (en) * | 1996-12-19 | 1998-06-25 | Smithkline Beecham Plc | Sulphonamide derivatives, process for their preparation, and their use as medicaments |
WO1998027058A3 (en) * | 1996-12-19 | 1998-08-20 | Smithkline Beecham Plc | N-piperazin-1-ylphenyl-benzamide derivatives |
US6599904B2 (en) | 1996-12-19 | 2003-07-29 | Smithkline Beecham P.L.C. | Sulphonamide derivatives, process for their preparation, and their use as medicaments |
EA002351B1 (en) * | 1996-12-19 | 2002-04-25 | Смитклайн Бичам Плс | Sulphonamide derivatives, process for their preparation, and their use as medicaments |
WO1998027058A2 (en) * | 1996-12-19 | 1998-06-25 | Smithkline Beecham Plc | N-piperazin-1-ylphenyl-benzamide derivatives |
US6423717B1 (en) | 1996-12-19 | 2002-07-23 | Smithkline Beecham P.L.C. | Sulphonamide derivatives, process for their preparation, and their use as medicaments |
US6291458B1 (en) | 1997-07-02 | 2001-09-18 | Astrazeneca Ab | Morpholinobenzamide salts |
US6534652B2 (en) | 1997-07-25 | 2003-03-18 | Astrazeneca Ab | Intermediates for the preparation of substituted 1,2,3,4-tetrahydronaphthalene derivatives |
US6313118B1 (en) | 1997-07-25 | 2001-11-06 | Astra Aktiebolag | Substituted 1,2,3,4-tetrahydronaphthalene derivatives |
US6410532B2 (en) | 1997-07-25 | 2002-06-25 | Astrazeneca Ab | Substituted 1,2,3,4-tetrahydronaphthalene derivatives |
WO2001009111A1 (en) * | 1999-07-29 | 2001-02-08 | Eli Lilly And Company | Benzofurylpiperazines and benzofurylhomopiperazines: serotonin agonists |
WO2001009123A1 (en) * | 1999-07-29 | 2001-02-08 | Eli Lilly And Company | Benzofurylpiperazine serotonin agonists |
US6638936B1 (en) | 1999-07-29 | 2003-10-28 | Eli Lilly And Company | Benzofurylpiperazine serotonin agonists |
US6967201B1 (en) | 1999-07-29 | 2005-11-22 | Eli Lilly And Company | Benzofurylpiperazines and benzofurylhomopiperazines: serotonin agonists |
US7166597B2 (en) | 2000-08-22 | 2007-01-23 | Glaxo Group Limited | Fused pyrazole derivatives being protein kinase inhibitors |
US6858592B2 (en) | 2001-06-29 | 2005-02-22 | Genzyme Corporation | Aryl boronic acids for treating obesity |
US7041280B2 (en) | 2001-06-29 | 2006-05-09 | Genzyme Corporation | Aryl boronate functionalized polymers for treating obesity |
US7049304B2 (en) | 2001-06-29 | 2006-05-23 | Genzyme Corporation | Aryl boronic acids for treating obesity |
US7456156B2 (en) | 2001-06-29 | 2008-11-25 | Genzyme Corporation | Aryl boronic acids for treating obesity |
US7557109B2 (en) | 2001-07-20 | 2009-07-07 | Psychogenics, Inc. | Treatment for attention-deficit hyperactivity disorder |
US7504395B2 (en) | 2001-07-20 | 2009-03-17 | Psychogenics, Inc. | Treatment for attention-deficit hyperactivity disorder |
US7166623B2 (en) | 2001-10-17 | 2007-01-23 | Glaxo Group Limited | 2′-Methyl-5′-(1,3,4-oxadiazol-2-yl)-1,1′-biphenyl-4-carboxamide derivatives and their use as p38 kinase inhibitors |
US7183297B2 (en) | 2001-10-17 | 2007-02-27 | Glaxo Group Limited | Biphenyl-derivatives as p38-kinase inhibitors |
US7208629B2 (en) | 2001-10-17 | 2007-04-24 | Glaxo Group Limited | 5′-Carbamoyl-1,1-biphenyl-4-carboxamide derivatives and their use as p38 kinase inhibitors |
US7309800B2 (en) | 2001-10-17 | 2007-12-18 | Glaxo Group Limited | Biphenylcarboxylic amide derivatives as p38 kinase inhibitors |
US7384963B2 (en) | 2001-10-17 | 2008-06-10 | Glaxo Group Limited | 2′-Methyl-5-(1,3,4-oxadiazol-2-yl)1, 1′-biphenyl-4-carboxaide derivatives and their use as p38 kinase |
US7396843B2 (en) | 2001-10-17 | 2008-07-08 | Glaxo Group Limited | 5′-carbamoyl-1,1′-biphenyl-4-carboxamide derivatives and their use as p38 kinase inhibitors |
US7432289B2 (en) | 2001-10-17 | 2008-10-07 | Glaxo Group Limited | 5-Acylamino-1,1′-biphenyl-4-carboxamide derivatives and their use as P38 kinase inhibitors |
US7151118B2 (en) | 2001-10-17 | 2006-12-19 | Glaxo Group Limited | Biphenylcarboxylic amide derivatives as p38-kinase inhibitors |
US7709506B2 (en) | 2002-02-12 | 2010-05-04 | Glaxosmithkline Llc | Nicotinamide derivatives useful as p38 inhibitors |
US7125898B2 (en) | 2002-02-12 | 2006-10-24 | Smithkline Beecham Corporation | Nicotinamide derivatives useful as p38 inhibitors. |
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US7642276B2 (en) | 2002-07-31 | 2010-01-05 | Smithkline Beecham Corporation | Fused heteroaryl derivatives for use as P38 kinase inhibitors |
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US7572790B2 (en) | 2003-04-09 | 2009-08-11 | Smithkline Beecham Corporation | Biphenyl carboxylic amide p38 kinase inhibitors |
US7271289B2 (en) | 2003-04-09 | 2007-09-18 | Smithkline Beecham Corporation | Biphenylcarboxylic amide derivatives as p38 kinase inhibitors |
US7838540B2 (en) | 2003-08-11 | 2010-11-23 | Glaxosmithkline Llc | 3-aminocarbonyl, 6-phenyl substituted pyridine-1-oxides as p38 kinase inhibitors |
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US20130310378A1 (en) * | 2007-08-27 | 2013-11-21 | Abbvie Inc. | 4-(4-pyridinyl)-benzamides and their use as rock activity modulators |
US8445686B2 (en) * | 2007-08-27 | 2013-05-21 | Abbvie Inc. | 4-(4-pyridinyl)-benzamides and their use as rock activity modulators |
US8895749B2 (en) | 2007-08-27 | 2014-11-25 | Abbvie Inc. | 4-(4-pyridinyl)-benzamides and their use as rock activity modulators |
WO2011098776A1 (en) | 2010-02-15 | 2011-08-18 | Cambridge Enterprise Limited | 5-ht receptor modulators |
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CN107108581A (en) * | 2014-08-21 | 2017-08-29 | 百时美施贵宝公司 | It is used as the tieback heterocyclic carbamate derivatives of potent ROCK inhibitor |
US10112939B2 (en) | 2014-08-21 | 2018-10-30 | Bristol-Myers Squibb Company | Tied-back benzamide derivatives as potent rock inhibitors |
US11498903B2 (en) | 2017-08-17 | 2022-11-15 | Bristol-Myers Squibb Company | 2-(1,1′-biphenyl)-1H-benzodimidazole derivatives and related compounds as apelin and APJ agonists for treating cardiovascular diseases |
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Also Published As
Publication number | Publication date |
---|---|
JPH09503773A (en) | 1997-04-15 |
EP0724580A1 (en) | 1996-08-07 |
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