NO300807B1 - Cykliske uretaner som er nyttige som antiarytmiske og antifibrillatoriske midler - Google Patents

Cykliske uretaner som er nyttige som antiarytmiske og antifibrillatoriske midler Download PDF

Info

Publication number: NO300807B1
Authority: NO; Norway
Prior art keywords: oxazolidinone; chlorophenyl; amino; furanyl; methylene
Prior art date: 1991-08-14

Application number

NO940496A

Other languages

English (en)

Norwegian (no)

Other versions

NO940496D0 (no

NO940496L (no

Inventor

Jr Stanford Salvatore Pelosi

Chia-Nien Yu

Original Assignee

Procter & Gamble Pharma

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.)

1991-08-14

Filing date

1994-02-14

Publication date

1997-07-28

1994-02-14 Application filed by Procter & Gamble Pharma filed Critical Procter & Gamble Pharma

1994-02-14 Publication of NO940496D0 publication Critical patent/NO940496D0/no

1994-02-14 Publication of NO940496L publication Critical patent/NO940496L/no

1997-07-28 Publication of NO300807B1 publication Critical patent/NO300807B1/no

Links

-1 Cyclic urethanes Chemical class 0.000 title claims abstract description 61
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150000002148 esters Chemical class 0.000 claims abstract description 7
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206010003119 arrhythmia Diseases 0.000 claims description 38
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239000008194 pharmaceutical composition Substances 0.000 claims description 19
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239000000314 lubricant Substances 0.000 claims description 14
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JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 7
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RJMXFJWYRCXGDU-UHFFFAOYSA-N 3-[[5-(4-chlorophenyl)furan-2-yl]methylideneamino]-5-(piperidin-1-ylmethyl)-1,3-oxazolidin-2-one Chemical compound C1=CC(Cl)=CC=C1C(O1)=CC=C1C=NN1C(=O)OC(CN2CCCCC2)C1 RJMXFJWYRCXGDU-UHFFFAOYSA-N 0.000 claims description 3
MYGMKSJZXXLNMQ-UHFFFAOYSA-N 3-[[5-(4-chlorophenyl)furan-2-yl]methylideneamino]-5-[(4-methylpiperazin-1-yl)methyl]-1,3-oxazolidin-2-one Chemical compound C1CN(C)CCN1CC1OC(=O)N(N=CC=2OC(=CC=2)C=2C=CC(Cl)=CC=2)C1 MYGMKSJZXXLNMQ-UHFFFAOYSA-N 0.000 claims description 3
FWSRMVZLMPFLJI-UHFFFAOYSA-N 3-[[5-(4-chlorophenyl)furan-2-yl]methylideneamino]-5-[3-(4-methylpiperazin-1-yl)propyl]-1,3-oxazolidin-2-one Chemical compound C1CN(C)CCN1CCCC1OC(=O)N(N=CC=2OC(=CC=2)C=2C=CC(Cl)=CC=2)C1 FWSRMVZLMPFLJI-UHFFFAOYSA-N 0.000 claims description 3
RZMPHPUAYIVJHB-UHFFFAOYSA-N 3-[[5-(4-chlorophenyl)furan-2-yl]methylideneamino]-5-[4-(4-methylpiperazin-1-yl)butyl]-1,3-oxazolidin-2-one Chemical compound C1CN(C)CCN1CCCCC1OC(=O)N(N=CC=2OC(=CC=2)C=2C=CC(Cl)=CC=2)C1 RZMPHPUAYIVJHB-UHFFFAOYSA-N 0.000 claims description 3
JONNKBYFBIVMBK-UHFFFAOYSA-N 3-[[5-(4-chlorophenyl)furan-2-yl]methylideneamino]-5-[[4-(2-hydroxyethyl)piperidin-1-yl]methyl]-1,3-oxazolidin-2-one Chemical compound C1CC(CCO)CCN1CC1OC(=O)N(N=CC=2OC(=CC=2)C=2C=CC(Cl)=CC=2)C1 JONNKBYFBIVMBK-UHFFFAOYSA-N 0.000 claims description 3
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MOAVUYWYFFCBNM-PUGKRICDSA-N digoxin(1-) Chemical compound C[C@H]([C@H]([C@H](C1)O)O)O[C@H]1O[C@H]([C@@H](C)O[C@H](C1)O[C@H]([C@@H](C)O[C@H](C2)O[C@@H](CC3)C[C@@H](CC4)[C@@]3(C)[C@@H](C[C@H]([C@]3(C)[C@H](CC5)C([CH-]O6)=CC6=O)O)[C@@H]4[C@]35O)[C@H]2O)[C@H]1O MOAVUYWYFFCBNM-PUGKRICDSA-N 0.000 description 1
LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 1
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208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000004821 distillation Methods 0.000 description 1
229940079593 drug Drugs 0.000 description 1
BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical compound CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
229960000449 flecainide Drugs 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
238000010413 gardening Methods 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229940014259 gelatin Drugs 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000001727 glucose Nutrition 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
230000036541 health Effects 0.000 description 1
230000004217 heart function Effects 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
230000001631 hypertensive effect Effects 0.000 description 1
230000006872 improvement Effects 0.000 description 1
230000007574 infarction Effects 0.000 description 1
230000000977 initiatory effect Effects 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000007794 irritation Effects 0.000 description 1
208000023589 ischemic disease Diseases 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
229940039717 lanolin Drugs 0.000 description 1
235000019388 lanolin Nutrition 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
125000005647 linker group Chemical group 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
238000007726 management method Methods 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000028161 membrane depolarization Effects 0.000 description 1
238000010197 meta-analysis Methods 0.000 description 1
229960002900 methylcellulose Drugs 0.000 description 1
208000019267 mild heart failure Diseases 0.000 description 1
UEHLXXJAWYWUGI-UHFFFAOYSA-M nitromersol Chemical compound CC1=CC=C([N+]([O-])=O)C2=C1O[Hg]2 UEHLXXJAWYWUGI-UHFFFAOYSA-M 0.000 description 1
229940118238 nitromersol Drugs 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
235000020824 obesity Nutrition 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
230000035699 permeability Effects 0.000 description 1
150000004965 peroxy acids Chemical class 0.000 description 1
239000012071 phase Substances 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
229940096826 phenylmercuric acetate Drugs 0.000 description 1
229940068196 placebo Drugs 0.000 description 1
239000000902 placebo Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
230000002265 prevention Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000008569 process Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
229960003712 propranolol Drugs 0.000 description 1
230000000306 recurrent effect Effects 0.000 description 1
230000003014 reinforcing effect Effects 0.000 description 1
230000002336 repolarization Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000008227 sterile water for injection Substances 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
208000014221 sudden cardiac arrest Diseases 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000002522 swelling effect Effects 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
238000012385 systemic delivery Methods 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
230000036962 time dependent Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 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
238000012384 transportation and delivery Methods 0.000 description 1
208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000003643 water by type Substances 0.000 description 1

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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Hydrogenated Pyridines (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Furan Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

NO940496A 1991-08-14 1994-02-14 Cykliske uretaner som er nyttige som antiarytmiske og antifibrillatoriske midler NO300807B1 (no)

Applications Claiming Priority (2)

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

Publications (3)

Publication Number	Publication Date
NO940496D0 NO940496D0 (no)	1994-02-14
NO940496L NO940496L (no)	1994-02-14
NO300807B1 true NO300807B1 (no)	1997-07-28

Family

ID=24994270

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO940496A NO300807B1 (no)	1991-08-14	1994-02-14	Cykliske uretaner som er nyttige som antiarytmiske og antifibrillatoriske midler

Country Status (23)

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

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CZ282368B6 (cs) *	1991-08-14	1997-07-16	Procter And Gamble Pharmaceuticals	4-Oxocyklické močoviny a faramceutický prostředek je obsahující
CA2115029C (en) *	1991-08-14	2002-03-26	Stanford Salvatore Pelosi, Jr.	Cyclic urethanes useful as antiarrhythmic and antifibrillatory agents
DK0598046T3 (da) *	1991-08-14	1999-05-25	Procter & Gamble Pharma	Hidtil ukendte urinstoffer egnede som antiarrytmi- og antifibrilleringsmidler
RU2194706C2 (ru)	1998-04-29	2002-12-20	Дзе Проктер Энд Гэмбл Компани	Способ получения дигидрохлорида 1-[[[5-(4-хлорфенил)-2-фуранил]метилен]амино]-3-[4-(4-метил-1-пиперазинил) бутил]-2,4-имидазолидиндиона
HUP0101356A3 (en)	1998-04-29	2003-08-28	Procter & Gamble	Process for making 1,3-disubstituted-4-oxocyclic ureas
KR20100072230A (ko) *	2007-09-26	2010-06-30	마운트 시나이 스쿨 오브 메디신 오브 뉴욕 유니버시티	아자시티딘 유사체 및 이의 용도

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JPH0276882A (ja) *	1988-06-20	1990-03-16	Eisai Co Ltd	光学活性ヒダントイン誘導体
DE68918792T2 (de) *	1988-09-15	1995-03-30	Upjohn Co	5-Indolinyl-5-beta-amidomethyloxazolidin-2-one, 3-(substituierte kondensierte)phenyl-5-beta amidomethyloxazolidin-2-one und 3-(Nitrogen-substituierte)phenyl-5-beta-amidomethyloxazolidin-2-one.
PH30434A (en) *	1989-04-07	1997-05-09	Janssen Pharmaceutica Nv	Hydroxyalkylfuranyl derivatives
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US4966967A (en) *	1989-09-15	1990-10-30	Berlex Laboratories, Inc.	3,4,5,6-tetrahydro-2H-1,7,4-benzodioxazonines as cardiovascular agents
US5032598A (en) *	1989-12-08	1991-07-16	Merck & Co., Inc.	Nitrogens containing heterocyclic compounds as class III antiarrhythmic agents
US4963561A (en) *	1990-02-28	1990-10-16	Sterling Drug Inc.	Imidazopyridines, their preparation and use
US5066662A (en) *	1990-05-21	1991-11-19	Warner-Lambert Company	Substituted oxazolidin-2-ones and 1,2,4-oxadiazolin-5-ones and derivatives thereof acting at muscarinic receptors
US5086055A (en) *	1990-12-24	1992-02-04	A. H. Robins Company, Incorporated	Series of 5-[-(4-aryl-1-piperazinyl)alkyl]-2-oxazolidinone derivatives useful in the treatment of allergic conditions
CA2115029C (en) *	1991-08-14	2002-03-26	Stanford Salvatore Pelosi, Jr.	Cyclic urethanes useful as antiarrhythmic and antifibrillatory agents

1992
- 1992-08-10 CA CA002115029A patent/CA2115029C/en not_active Expired - Fee Related
- 1992-08-10 CZ CZ94278A patent/CZ283323B6/cs not_active IP Right Cessation
- 1992-08-10 EP EP92918216A patent/EP0599968B1/en not_active Expired - Lifetime
- 1992-08-10 PL PL92302375A patent/PL171280B1/pl unknown
- 1992-08-10 DK DK92918216T patent/DK0599968T3/da active
- 1992-08-10 ES ES92918216T patent/ES2141725T3/es not_active Expired - Lifetime
- 1992-08-10 AT AT92918216T patent/ATE188696T1/de not_active IP Right Cessation
- 1992-08-10 SK SK169-94A patent/SK16994A3/sk unknown
- 1992-08-10 HU HU9400403A patent/HUT70144A/hu unknown
- 1992-08-10 AU AU24678/92A patent/AU665367B2/en not_active Ceased
- 1992-08-10 JP JP5504374A patent/JPH06510285A/ja active Pending
- 1992-08-10 WO PCT/US1992/006682 patent/WO1993004064A1/en active IP Right Grant
- 1992-08-10 RU RU94016524A patent/RU2125568C1/ru active
- 1992-08-10 BR BR9206353A patent/BR9206353A/pt not_active Application Discontinuation
- 1992-08-10 DE DE69230563T patent/DE69230563T2/de not_active Expired - Fee Related
- 1992-08-12 IL IL102791A patent/IL102791A/en not_active IP Right Cessation
- 1992-08-13 NZ NZ243936A patent/NZ243936A/en unknown
- 1992-08-14 PT PT100775A patent/PT100775B/pt not_active IP Right Cessation
- 1992-08-14 MX MX9204736A patent/MX9204736A/es not_active IP Right Cessation
1994
- 1994-02-11 FI FI940658A patent/FI940658A0/fi unknown
- 1994-02-14 NO NO940496A patent/NO300807B1/no unknown
1995
- 1995-06-07 US US08/479,254 patent/US5994354A/en not_active Expired - Fee Related
1999
- 1999-04-23 EP EP99107448A patent/EP0957103A1/en not_active Withdrawn
2000
- 2000-01-19 GR GR20000400129T patent/GR3032432T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE69230563D1 (de)	2000-02-17
CA2115029A1 (en)	1993-03-04
EP0957103A1 (en)	1999-11-17
CA2115029C (en)	2002-03-26
GR3032432T3 (en)	2000-05-31
WO1993004064A1 (en)	1993-03-04
US5994354A (en)	1999-11-30
RU2125568C1 (ru)	1999-01-27
PT100775B (pt)	1999-09-30
DE69230563T2 (de)	2000-09-14
NZ243936A (en)	1996-10-28
CZ27894A3 (en)	1995-07-12
ES2141725T3 (es)	2000-04-01
FI940658A (fi)	1994-02-11
FI940658A0 (fi)	1994-02-11
PT100775A (pt)	1994-01-31
AU665367B2 (en)	1996-01-04
CZ283323B6 (cs)	1998-02-18
NO940496D0 (no)	1994-02-14
IL102791A (en)	1998-06-15
PL171280B1 (pl)	1997-03-28
MX9204736A (es)	1993-11-01
EP0599968B1 (en)	2000-01-12
SK16994A3 (en)	1995-03-08
NO940496L (no)	1994-02-14
HUT70144A (en)	1995-09-28
DK0599968T3 (da)	2000-04-17
ATE188696T1 (de)	2000-01-15
IL102791A0 (en)	1993-01-31
BR9206353A (pt)	1995-11-07
HU9400403D0 (en)	1994-05-30
JPH06510285A (ja)	1994-11-17
AU2467892A (en)	1993-03-16
EP0599968A1 (en)	1994-06-08

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RU2142461C1 (ru)	1999-12-10	Циклические соединения мочевины, фармацевтическая композиция и способ лечения
US6083945A (en)	2000-07-04	Cyclic ureas useful as antiarrhythmic and antifibrillatory agents
JP3347691B2 (ja)	2002-11-20	抗不整脈及び抗細動剤として有用な新規４−オキソ環式尿素類