CA2115029A1 - Cyclic urethanes useful as antiarrhythmic and antifibrillatory agents - Google Patents

Cyclic urethanes useful as antiarrhythmic and antifibrillatory agents

Info

Publication number
CA2115029A1
CA2115029A1 CA002115029A CA2115029A CA2115029A1 CA 2115029 A1 CA2115029 A1 CA 2115029A1 CA 002115029 A CA002115029 A CA 002115029A CA 2115029 A CA2115029 A CA 2115029A CA 2115029 A1 CA2115029 A1 CA 2115029A1
Authority
CA
Canada
Prior art keywords
nil
unsubstituted
saturated
substituted
unsaturated
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.)
Granted
Application number
CA002115029A
Other languages
French (fr)
Other versions
CA2115029C (en
Inventor
Stanford Salvatore Pelosi, Jr.
Chia-Nien Yu
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Warner Chilcott Pharmaceuticals Inc
Original Assignee
Stanford Salvatore Pelosi, Jr.
Chia-Nien Yu
Norwich Eaton Pharmaceuticals, Inc.
Procter & Gamble Pharmaceuticals, Inc.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Stanford Salvatore Pelosi, Jr., Chia-Nien Yu, Norwich Eaton Pharmaceuticals, Inc., Procter & Gamble Pharmaceuticals, Inc. filed Critical Stanford Salvatore Pelosi, Jr.
Publication of CA2115029A1 publication Critical patent/CA2115029A1/en
Application granted granted Critical
Publication of CA2115029C publication Critical patent/CA2115029C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • 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
    • C07D413/10—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 carbon chain containing aromatic rings
    • 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
    • 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
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Abstract

The novel cyclic urethanes, and their pharmaceutically-acceptable salts and esters, described herein which are useful as an-tiarrhythmic and antifibrillatory agents and have general structure (I), wherein (a) X is a saturated or unsaturated, 5-, 6-, or 7-membered heterocycle or carbocycle; (b) R is selected from the group consisting of covalent bond, nil, heteroatom, carbonyl, heterocyclic ring, carbocyclic ring, alkyl, alkenyl, alkoxy, alkylamino, arylalkyl, aryloxy, acyl, acyloxy, and acylamino; (c) Y is a substituted or unsubstituted, saturated or unsaturated, 5-, 6-, or 7-membered heterocyclic ring or carbocyclic ring, or is nil; and wherein when R is nil, X and Y are fused ring systems; and when R is a covalent bond, X and Y are ring systems linked through a covalent bond; and when Y is nil, R is a covalent bond, and X is a carbocycle bound to L through R; (d) R1, R2, and R3 are independently selected from the group consisting of nil, Cl, F, Br, NH2, CF3, OH, SO3H, CH3SO2NH, COOH, alkoxy, al-kyl, alkoxycarbonyl, hydroxyalkyl, carboxyalkyl, aminoalkyl, acylamino, and acyloxy; (e) L is selected from the group con-sisting of alkylamino, alkenylamino, alkylimino, alkenylimino and acylamino;
wherein the nitrogen atom'thereof is bound to the nitrogen atom at the 3-position of the cyclic urethane ring moiety; (f) R4 is selected from the group consisting of alkyl, alkenyl, alkynyl, alkylacyl, and heteroalkyl; (g) A is a substituted or unsubstituted, saturated or unsaturated, straight-chain or branched, C1-C8 heteroalkyl; or a substituted or unsubstituted, saturated or unsaturated heterocycle having 6- or 7-mem-bers which may not have an oxygen atom; and A has one nitrogen atom which is adjacent to R4; and (h) R5 is a substituted or unsubstituted C1 or C2 alkyl; and the pharmaceutically-acceptable salts and esters thereof.
CA002115029A 1991-08-14 1992-08-10 Cyclic urethanes useful as antiarrhythmic and antifibrillatory agents Expired - Fee Related CA2115029C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US74486591A 1991-08-14 1991-08-14
US744,865 1991-08-14
PCT/US1992/006682 WO1993004064A1 (en) 1991-08-14 1992-08-10 Cyclic urethanes useful as antiarrhythmic and antifibrillatory agents

Publications (2)

Publication Number Publication Date
CA2115029A1 true CA2115029A1 (en) 1993-03-04
CA2115029C CA2115029C (en) 2002-03-26

Family

ID=24994270

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002115029A Expired - Fee Related CA2115029C (en) 1991-08-14 1992-08-10 Cyclic urethanes useful as antiarrhythmic and antifibrillatory agents

Country Status (23)

Country Link
US (1) US5994354A (en)
EP (2) EP0599968B1 (en)
JP (1) JPH06510285A (en)
AT (1) ATE188696T1 (en)
AU (1) AU665367B2 (en)
BR (1) BR9206353A (en)
CA (1) CA2115029C (en)
CZ (1) CZ283323B6 (en)
DE (1) DE69230563T2 (en)
DK (1) DK0599968T3 (en)
ES (1) ES2141725T3 (en)
FI (1) FI940658A0 (en)
GR (1) GR3032432T3 (en)
HU (1) HUT70144A (en)
IL (1) IL102791A (en)
MX (1) MX9204736A (en)
NO (1) NO300807B1 (en)
NZ (1) NZ243936A (en)
PL (1) PL171280B1 (en)
PT (1) PT100775B (en)
RU (1) RU2125568C1 (en)
SK (1) SK16994A3 (en)
WO (1) WO1993004064A1 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE69232825D1 (en) * 1991-08-14 2002-11-21 Procter & Gamble Pharma Cyclic ureas with antiarrhythmic and antifibrillatory effects
CZ283323B6 (en) * 1991-08-14 1998-02-18 Procter And Gamble Pharmaceuticals, Inc. Cyclic urethanes and pharmaceutical composition containing thereof
ES2180537T3 (en) * 1991-08-14 2003-02-16 Procter & Gamble Pharma NEW 4-OXOCICLIC UREAS, USED AS ANTIARRITHMIC OR ANTIFIBRILLATING AGENTS.
DE69920003T2 (en) 1998-04-29 2005-09-15 The Procter & Gamble Company, Cincinnati PROCESS FOR THE PREPARATION OF 1,3-DISUBSTITUTED-4-OXOCYCLIC UREASES
AU751681B2 (en) 1998-04-29 2002-08-22 Lonza Ltd. Process for making 1,3-disubstituted-4-oxocyclic ureas
UA99308C2 (en) * 2007-09-26 2012-08-10 Маунт Синай Скул Оф Медсин Azacytidine analogue and use thereof

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GB843834A (en) * 1957-05-13 1960-08-10 Norwich Pharma Co N-(5-nitro-2-furyl)-alkylidene-3-amino-5-tertiaryaminomethyl-2-oxazolidones and chemotherapeutic compositions containing them
FR1274399A (en) * 1958-01-23 1961-10-27 Norwich Pharma Co Improved process for the preparation of 5-nitro-2-formyl-furan derivatives
NL104211C (en) * 1958-02-28
US3004888A (en) * 1959-01-12 1961-10-17 Pfizer & Co C Mastitis treatment
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FR385M (en) * 1960-08-17 1961-03-24 Norwich Pharma Co New drug for the treatment of staphylococcal infections and the like.
CH398599A (en) * 1961-03-24 1966-03-15 Om Lab Sa Process for the preparation of α-bromo-B- (5-nitro-2-furyl) acrolein hydrazones
BE633841A (en) * 1962-06-21
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US3415821A (en) * 1965-09-07 1968-12-10 Norwich Pharma Co 1-(5-substituted)furfurylideneamino hydantoins and imidazolidinones
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GB1279408A (en) * 1968-09-12 1972-06-28 Ciba Geigy Ag 5-nitro-2-furfurylideneamino-oxazolidinones
US3839567A (en) * 1969-04-17 1974-10-01 Schering Ag Pharmaceutical compositions comprising 3-(5-nitro-2-imidazolyl-methylen-amino)-2-oxazolidinones and their use in trichomoniasia
US3906101A (en) * 1969-06-05 1975-09-16 Ciba Geigy Corp Pharmaceutical compositions containing substituted 5-nitrofurfurylideneamino-oxazolidinones
US4775670A (en) * 1980-09-29 1988-10-04 E. R. Squibb & Sons, Inc. 2-oxo-1-azetidinesulfonic acid salts
US4393204A (en) * 1982-05-21 1983-07-12 Norwich Eaton Pharmaceuticals, Inc. 3-[[5-(4-Chlorophenyl)furfurylidene]amino]-5-(substituted)-2-oxazolidinones
US4543359A (en) * 1982-10-01 1985-09-24 Eaton Laboratories, Inc. Treating cardiac arrhythmias with dantrolene sodium
US4705799A (en) * 1983-06-07 1987-11-10 E. I. Du Pont De Nemours And Company Aminomethyl oxooxazolidinyl benzenes useful as antibacterial agents
US4581370A (en) * 1983-07-12 1986-04-08 Schering A.G. Antiarrhythmic imidazoliums
US4720580A (en) * 1984-09-21 1988-01-19 American Home Products Corporation N-(aminoalkylene)benzenesulfonamides
US4707499A (en) * 1985-12-02 1987-11-17 G. D. Searle & Co. 3-alkyl-5-(substituted amino)methyl)dihydro-3-phenyl-2(3H)-furanones and imino analogs thereof used for treatment of arrhythmia
PH23283A (en) * 1986-02-26 1989-06-30 Eisai Co Ltd Piperidine derivative, pharmaceutical composition containing the same and method of use thereof
US4713832A (en) * 1986-04-11 1987-12-15 Ampex Corporation Programmable divider up/down counter with anti-aliasing feature and asynchronous read/write
IL79174A0 (en) * 1986-06-05 1986-09-30 Abic Ltd Water soluble salt of furaltadone
US4895867A (en) * 1986-06-26 1990-01-23 Norwich Eaton Pharmaceuticals, Inc. 2-(5-phenyl-2-furanyl)imidazoles useful as cardiotonic agents
US4886794A (en) * 1987-05-07 1989-12-12 A. H. Robins Company, Incorporated 4-[(α,α-diaryl)-hydroxymethyl]-1-piperidinylalkyl-cyclic carbamate derivatives as allergic response inhibitors
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CZ283323B6 (en) * 1991-08-14 1998-02-18 Procter And Gamble Pharmaceuticals, Inc. Cyclic urethanes and pharmaceutical composition containing thereof

Also Published As

Publication number Publication date
PT100775A (en) 1994-01-31
FI940658A (en) 1994-02-11
AU2467892A (en) 1993-03-16
NZ243936A (en) 1996-10-28
PT100775B (en) 1999-09-30
EP0957103A1 (en) 1999-11-17
NO300807B1 (en) 1997-07-28
US5994354A (en) 1999-11-30
IL102791A (en) 1998-06-15
SK16994A3 (en) 1995-03-08
HUT70144A (en) 1995-09-28
DK0599968T3 (en) 2000-04-17
BR9206353A (en) 1995-11-07
HU9400403D0 (en) 1994-05-30
MX9204736A (en) 1993-11-01
NO940496D0 (en) 1994-02-14
JPH06510285A (en) 1994-11-17
CA2115029C (en) 2002-03-26
PL171280B1 (en) 1997-03-28
DE69230563D1 (en) 2000-02-17
FI940658A0 (en) 1994-02-11
EP0599968A1 (en) 1994-06-08
DE69230563T2 (en) 2000-09-14
EP0599968B1 (en) 2000-01-12
ES2141725T3 (en) 2000-04-01
AU665367B2 (en) 1996-01-04
CZ283323B6 (en) 1998-02-18
IL102791A0 (en) 1993-01-31
CZ27894A3 (en) 1995-07-12
RU2125568C1 (en) 1999-01-27
NO940496L (en) 1994-02-14
ATE188696T1 (en) 2000-01-15
GR3032432T3 (en) 2000-05-31
WO1993004064A1 (en) 1993-03-04

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