CA2196064A1 - Derives 4-(4-methanesulfonamidophenyl)butylamine exercant une activite antiarhythmique - Google Patents
Derives 4-(4-methanesulfonamidophenyl)butylamine exercant une activite antiarhythmiqueInfo
- Publication number
- CA2196064A1 CA2196064A1 CA002196064A CA2196064A CA2196064A1 CA 2196064 A1 CA2196064 A1 CA 2196064A1 CA 002196064 A CA002196064 A CA 002196064A CA 2196064 A CA2196064 A CA 2196064A CA 2196064 A1 CA2196064 A1 CA 2196064A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- mixture
- phenyl
- butyl
- 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
- 230000003288 anthiarrhythmic effect Effects 0.000 title description 2
- ZXUAQIATMZIDSA-UHFFFAOYSA-N n-[4-(4-aminobutyl)phenyl]methanesulfonamide Chemical class CS(=O)(=O)NC1=CC=C(CCCCN)C=C1 ZXUAQIATMZIDSA-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 3
- 206010003119 arrhythmia Diseases 0.000 claims abstract description 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 239000003814 drug Substances 0.000 claims description 15
- 239000002552 dosage form Substances 0.000 claims description 3
- RSJCIZBBOMQVMZ-UHFFFAOYSA-N n-[4-[4-[ethyl(6-fluoroheptyl)amino]butyl]phenyl]methanesulfonamide Chemical compound CC(F)CCCCCN(CC)CCCCC1=CC=C(NS(C)(=O)=O)C=C1 RSJCIZBBOMQVMZ-UHFFFAOYSA-N 0.000 claims 1
- VHZZMAQDUUCEGX-UHFFFAOYSA-N n-[4-[4-[ethyl(7-fluoroheptyl)amino]butyl]phenyl]methanesulfonamide Chemical compound FCCCCCCCN(CC)CCCCC1=CC=C(NS(C)(=O)=O)C=C1 VHZZMAQDUUCEGX-UHFFFAOYSA-N 0.000 claims 1
- VWTBOSJXWUXAQO-UHFFFAOYSA-N n-[4-[4-[ethyl-(6-fluoro-6-methylheptyl)amino]butyl]phenyl]methanesulfonamide Chemical compound CC(F)(C)CCCCCN(CC)CCCCC1=CC=C(NS(C)(=O)=O)C=C1 VWTBOSJXWUXAQO-UHFFFAOYSA-N 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 23
- 238000000034 method Methods 0.000 abstract description 3
- 239000003416 antiarrhythmic agent Substances 0.000 abstract 1
- 230000004060 metabolic process Effects 0.000 abstract 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical class CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
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- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
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- 101100333758 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) ERP3 gene Proteins 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
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- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 229960002872 tocainide Drugs 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 239000012224 working solution Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- 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
- A61P9/06—Antiarrhythmics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Méthanesulfonamides de la formule (I), ou leurs sels pharmaceutiquement acceptables. Dans cette formule, R¿3? et un C¿1-7? alkyle substitué par un C¿3-7? cycloalkyle, ou un C¿1-10? alkyle substitué par 1 à 8 atomes de fluore, 1 à 3 substituants hydroxy, 1 à 3 substituants C¿1-5? acyloxy ou 1 à 3 substituants de C¿1-4? alcoxy. Ces composés se révèlent utiles comme agents antiarhythmiques de la classe III et se révèlent stables par rapport à un métabolisme rapide. L'invention porte également sur des méthodes de traitement des arhythmies cardiaques à l'aide de composés de la formule (I) ainsi que de compositions issues de ces composés.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30467394A | 1994-09-12 | 1994-09-12 | |
| US304,673 | 1994-09-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2196064A1 true CA2196064A1 (fr) | 1996-03-21 |
Family
ID=23177488
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002196064A Abandoned CA2196064A1 (fr) | 1994-09-12 | 1995-08-23 | Derives 4-(4-methanesulfonamidophenyl)butylamine exercant une activite antiarhythmique |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0781273A1 (fr) |
| JP (1) | JPH10505829A (fr) |
| AU (1) | AU688117B2 (fr) |
| CA (1) | CA2196064A1 (fr) |
| WO (1) | WO1996008471A1 (fr) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0164865B1 (fr) * | 1984-05-04 | 1988-12-21 | The Upjohn Company | N-(aminoalcoylphényl)sulfonamides, leur préparation et leur utilisation thérapeutique |
| US4569801A (en) * | 1984-10-15 | 1986-02-11 | Eli Lilly And Company | Alkylsulfonamidophenylalkylamines |
| EP0484378B1 (fr) * | 1989-07-25 | 1994-09-14 | The Upjohn Company | Amine-alcenyle-phenyle-alcanesulfonamides tertiaires antiarythmiques |
| US5208252A (en) * | 1992-07-24 | 1993-05-04 | Ortho Pharmaceutical Corporation | Aminoethylthiophene derivatives |
-
1995
- 1995-08-23 CA CA002196064A patent/CA2196064A1/fr not_active Abandoned
- 1995-08-23 WO PCT/US1995/010424 patent/WO1996008471A1/fr not_active Ceased
- 1995-08-23 EP EP95930837A patent/EP0781273A1/fr not_active Ceased
- 1995-08-23 AU AU34070/95A patent/AU688117B2/en not_active Expired - Fee Related
- 1995-08-23 JP JP8510190A patent/JPH10505829A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPH10505829A (ja) | 1998-06-09 |
| WO1996008471A1 (fr) | 1996-03-21 |
| EP0781273A1 (fr) | 1997-07-02 |
| AU688117B2 (en) | 1998-03-05 |
| AU3407095A (en) | 1996-03-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Dead |