IL105270A - Parental solutions containing 3-dialkylaminoatoxybenzoyl-benzopurans - Google Patents

Parental solutions containing 3-dialkylaminoatoxybenzoyl-benzopurans

Info

Publication number: IL105270A
Authority: IL; Israel
Prior art keywords: amiodarone; solution; acetate buffer; acetate; concentration
Prior art date: 1992-04-01

Application number

IL10527093A

Other languages

English (en)

Hebrew (he)

Other versions

IL105270A0 (en

Original Assignee

Academic Pharmaceuticals

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.)

1992-04-01

Filing date

1993-04-01

Publication date

1999-11-30

1993-04-01 Application filed by Academic Pharmaceuticals filed Critical Academic Pharmaceuticals

1993-08-18 Publication of IL105270A0 publication Critical patent/IL105270A0/xx

1999-11-30 Publication of IL105270A publication Critical patent/IL105270A/en

Links

239000003182 parenteral nutrition solution Substances 0.000 title abstract description 10
229960005260 amiodarone Drugs 0.000 claims abstract description 116
239000008351 acetate buffer Substances 0.000 claims abstract description 65
IYIKLHRQXLHMJQ-UHFFFAOYSA-N amiodarone Chemical compound CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCCN(CC)CC)C(I)=C1 IYIKLHRQXLHMJQ-UHFFFAOYSA-N 0.000 claims abstract description 22
-1 amiodarone Chemical class 0.000 claims abstract description 11
206010003119 arrhythmia Diseases 0.000 claims abstract description 10
230000006793 arrhythmia Effects 0.000 claims abstract description 10
239000000243 solution Substances 0.000 claims description 102
238000002360 preparation method Methods 0.000 claims description 29
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 28
238000001990 intravenous administration Methods 0.000 claims description 25
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 12
230000003288 anthiarrhythmic effect Effects 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
239000011780 sodium chloride Substances 0.000 claims description 10
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 8
239000004480 active ingredient Substances 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
239000003416 antiarrhythmic agent Substances 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 8
150000001875 compounds Chemical class 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
238000007911 parenteral administration Methods 0.000 claims description 5
239000008121 dextrose Substances 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical class CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 claims description 2
238000010438 heat treatment Methods 0.000 claims description 2
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 3
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims 2
150000002431 hydrogen Chemical class 0.000 claims 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
150000001907 coumarones Chemical class 0.000 claims 1
125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
IHEKAGRGYOAFAL-UHFFFAOYSA-N 1-benzofuran-2-yl-[3-[2-(diethylamino)ethoxy]phenyl]methanone Chemical class CCN(CC)CCOC1=CC=CC(C(=O)C=2OC3=CC=CC=C3C=2)=C1 IHEKAGRGYOAFAL-UHFFFAOYSA-N 0.000 abstract 1
ITPDYQOUSLNIHG-UHFFFAOYSA-N Amiodarone hydrochloride Chemical compound [Cl-].CCCCC=1OC2=CC=CC=C2C=1C(=O)C1=CC(I)=C(OCC[NH+](CC)CC)C(I)=C1 ITPDYQOUSLNIHG-UHFFFAOYSA-N 0.000 description 137
229940088540 cordarone Drugs 0.000 description 41
239000002244 precipitate Substances 0.000 description 14
241000700159 Rattus Species 0.000 description 13
230000000694 effects Effects 0.000 description 13
230000008859 change Effects 0.000 description 12
235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 12
229920000053 polysorbate 80 Polymers 0.000 description 12
230000000747 cardiac effect Effects 0.000 description 11
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
238000010265 fast atom bombardment Methods 0.000 description 9
206010047302 ventricular tachycardia Diseases 0.000 description 8
239000000872 buffer Substances 0.000 description 7
239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 7
229940068968 polysorbate 80 Drugs 0.000 description 7
230000002861 ventricular Effects 0.000 description 7
208000003663 ventricular fibrillation Diseases 0.000 description 7
IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
230000036772 blood pressure Effects 0.000 description 6
238000011095 buffer preparation Methods 0.000 description 6
229940079593 drug Drugs 0.000 description 6
WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
230000001154 acute effect Effects 0.000 description 5
238000010183 spectrum analysis Methods 0.000 description 5
208000001778 Coronary Occlusion Diseases 0.000 description 4
230000002763 arrhythmic effect Effects 0.000 description 4
239000007853 buffer solution Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
231100000517 death Toxicity 0.000 description 4
230000034994 death Effects 0.000 description 4
230000002526 effect on cardiovascular system Effects 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
239000000047 product Substances 0.000 description 4
231100000419 toxicity Toxicity 0.000 description 4
230000001988 toxicity Effects 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
206010011086 Coronary artery occlusion Diseases 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
235000019445 benzyl alcohol Nutrition 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
230000000052 comparative effect Effects 0.000 description 3
230000035487 diastolic blood pressure Effects 0.000 description 3
239000002552 dosage form Substances 0.000 description 3
231100000673 dose–response relationship Toxicity 0.000 description 3
230000001077 hypotensive effect Effects 0.000 description 3
210000005240 left ventricle Anatomy 0.000 description 3
229960001412 pentobarbital Drugs 0.000 description 3
230000009467 reduction Effects 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
230000001629 suppression Effects 0.000 description 3
206010005746 Blood pressure fluctuation Diseases 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
208000001871 Tachycardia Diseases 0.000 description 2
206010047281 Ventricular arrhythmia Diseases 0.000 description 2
KMOOJNVASSJPGR-UHFFFAOYSA-N acetic acid;1-benzofuran Chemical class CC(O)=O.C1=CC=C2OC=CC2=C1 KMOOJNVASSJPGR-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000003708 ampul Substances 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
230000000994 depressogenic effect Effects 0.000 description 2
230000003205 diastolic effect Effects 0.000 description 2
239000006207 intravenous dosage form Substances 0.000 description 2
125000002346 iodo group Chemical group I* 0.000 description 2
239000000463 material Substances 0.000 description 2
238000005259 measurement Methods 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
230000003389 potentiating effect Effects 0.000 description 2
238000011552 rat model Methods 0.000 description 2
239000002904 solvent Substances 0.000 description 2
230000035488 systolic blood pressure Effects 0.000 description 2
238000000108 ultra-filtration Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
DZRJNLPOTUVETG-UHFFFAOYSA-N 1-benzofuran-2-yl(phenyl)methanone Chemical class C=1C2=CC=CC=C2OC=1C(=O)C1=CC=CC=C1 DZRJNLPOTUVETG-UHFFFAOYSA-N 0.000 description 1
206010003658 Atrial Fibrillation Diseases 0.000 description 1
208000024172 Cardiovascular disease Diseases 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
208000010496 Heart Arrest Diseases 0.000 description 1
208000001953 Hypotension Diseases 0.000 description 1
206010049694 Left Ventricular Dysfunction Diseases 0.000 description 1
229910021607 Silver chloride Inorganic materials 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
206010042600 Supraventricular arrhythmias Diseases 0.000 description 1
230000009471 action Effects 0.000 description 1
230000004075 alteration Effects 0.000 description 1
229960003234 amiodarone hydrochloride Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
230000004872 arterial blood pressure Effects 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
210000001715 carotid artery Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
238000011109 contamination Methods 0.000 description 1
230000008602 contraction Effects 0.000 description 1
230000001595 contractor effect Effects 0.000 description 1
210000004351 coronary vessel Anatomy 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000001186 cumulative effect Effects 0.000 description 1
230000006735 deficit Effects 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
239000003599 detergent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
229940000406 drug candidate Drugs 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000002600 fibrillogenic effect Effects 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
230000000004 hemodynamic effect Effects 0.000 description 1
230000036543 hypotension Effects 0.000 description 1
230000001771 impaired effect Effects 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000004041 inotropic agent Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
231100000225 lethality Toxicity 0.000 description 1
230000007774 longterm Effects 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000012528 membrane Substances 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
238000012544 monitoring process Methods 0.000 description 1
230000002107 myocardial effect Effects 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
239000007935 oral tablet Substances 0.000 description 1
229940096978 oral tablet Drugs 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
230000037361 pathway Effects 0.000 description 1
230000002093 peripheral effect Effects 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
230000002028 premature Effects 0.000 description 1
230000008569 process Effects 0.000 description 1
230000000750 progressive effect Effects 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
230000000306 recurrent effect Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 1
229940071536 silver acetate Drugs 0.000 description 1
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000012453 sprague-dawley rat model Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
230000024883 vasodilation Effects 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/12—Carboxylic acids; Salts or anhydrides thereof
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
- 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

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Epidemiology (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Dermatology (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Furan Compounds (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Medicinal Preparation (AREA)
Cosmetics (AREA)

IL10527093A 1992-04-01 1993-04-01 Parental solutions containing 3-dialkylaminoatoxybenzoyl-benzopurans IL105270A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/861,608 US5234949A (en)	1992-04-01	1992-04-01	Parenteral solutions containing amiodarone in acetate buffer solution

Publications (2)

Publication Number	Publication Date
IL105270A0 IL105270A0 (en)	1993-08-18
IL105270A true IL105270A (en)	1999-11-30

Family

ID=25336272

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10527093A IL105270A (en)	1992-04-01	1993-04-01	Parental solutions containing 3-dialkylaminoatoxybenzoyl-benzopurans

Country Status (10)

Country	Link
US (1)	US5234949A (de)
EP (1)	EP0633777B1 (de)
JP (1)	JP3253302B2 (de)
AT (1)	ATE172115T1 (de)
AU (1)	AU3969593A (de)
CA (1)	CA2133324C (de)
DE (1)	DE69321585T2 (de)
IL (1)	IL105270A (de)
WO (1)	WO1993019753A1 (de)
ZA (1)	ZA932304B (de)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2735978B1 (fr) *	1995-06-30	1997-09-19	Sanofi Sa	Composition pharmaceutique d'amiodarone pour administration parenterale
US6030998A (en) *	1997-06-27	2000-02-29	Academic Pharmaceuticals, Lp	Methods for treating arrhythmia using acetate buffer solutions of amiodarone
US5981514A (en) *	1998-02-12	1999-11-09	Somberg; John C.	(N-alkyl-N-hydroxymethylamino)alkoxybenzoylbenzofurans and the phosphate esters thereof
US6479541B1 (en)	2000-03-30	2002-11-12	Baxter International	Amiodarone-containing parenteral administration
US20020143051A1 (en)	2001-03-29	2002-10-03	Doty Mark J.	Premixed amiodarone parenteral solution and method for making the same
EP1372637B1 (de) *	2001-03-29	2008-02-20	Baxter International Inc.	Vorgemischte amiodaron-haltige parenterale lösung und deren herstellungsverfahren
RU2192855C1 (ru) *	2001-12-10	2002-11-20	Сыров Кирилл Константинович	Способ получения лекарственного средства для инъекций на основе амиодарона
US6869939B2 (en) *	2002-05-04	2005-03-22	Cydex, Inc.	Formulations containing amiodarone and sulfoalkyl ether cyclodextrin
US20090270496A1 (en) *	2007-05-03	2009-10-29	Courchesne William E	Antifungal compounds
EP2335686A1 (de)	2009-12-21	2011-06-22	LEK Pharmaceuticals d.d.	Wässrige intravenöse Nanosuspension mit minimalen Nebenwirkungen
WO2011156481A2 (en)	2010-06-11	2011-12-15	Baxter International Inc.	Formulations including amiodarone and salts thereof and methods of their manufacture and use
US9642828B2 (en)	2014-09-23	2017-05-09	Sun Pharmaceutical Industries Limited	Parenteral dosage form of amiodarone

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3248401A (en) *		1966-04-26		Diethylaminoe hoxybenzoyl benzofurans
FR2550091B1 (fr) *	1983-08-02	1986-05-23	Sanofi Sa	Composition pharmaceutique ou veterinaire destinee a combattre des troubles ischemiques cardiaques contenant un derive du benzofuranne
US4831054A (en) *	1988-04-18	1989-05-16	Taro Pharmaceuticals, Ltd.	2-Alkyl-3-benzoylbenzofurans useful for treating cardiac arrhythmia
ATE89164T1 (de) *	1989-02-20	1993-05-15	Soorianarain Baligadoo	Pharmazeutische herzschuetzende zusammensetzungen enthaltend amiodaron, ein nitroderivat, naemlich isosorbiddinitrat, und gegebenenfalls einen betablocker.

1992
- 1992-04-01 US US07/861,608 patent/US5234949A/en not_active Expired - Lifetime
1993
- 1993-03-29 DE DE69321585T patent/DE69321585T2/de not_active Expired - Fee Related
- 1993-03-29 AU AU39695/93A patent/AU3969593A/en not_active Abandoned
- 1993-03-29 EP EP93909194A patent/EP0633777B1/de not_active Expired - Lifetime
- 1993-03-29 CA CA002133324A patent/CA2133324C/en not_active Expired - Fee Related
- 1993-03-29 AT AT93909194T patent/ATE172115T1/de not_active IP Right Cessation
- 1993-03-29 JP JP51760193A patent/JP3253302B2/ja not_active Expired - Fee Related
- 1993-03-29 WO PCT/US1993/002919 patent/WO1993019753A1/en not_active Ceased
- 1993-03-31 ZA ZA932304A patent/ZA932304B/xx unknown
- 1993-04-01 IL IL10527093A patent/IL105270A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
US5234949A (en)	1993-08-10
CA2133324A1 (en)	1993-10-14
DE69321585T2 (de)	1999-03-04
EP0633777A1 (de)	1995-01-18
AU3969593A (en)	1993-11-08
ZA932304B (en)	1994-09-15
JPH08500330A (ja)	1996-01-16
ATE172115T1 (de)	1998-10-15
DE69321585D1 (de)	1998-11-19
EP0633777B1 (de)	1998-10-14
WO1993019753A1 (en)	1993-10-14
IL105270A0 (en)	1993-08-18
JP3253302B2 (ja)	2002-02-04
CA2133324C (en)	2005-02-01

Legal Events

Date	Code	Title
2000-06-01	FF	Patent granted
2000-08-31	KB	Patent renewed
2004-01-04	RH1	Patent not in force

Publication	Publication Date	Title
US3773939A (en)	1973-11-20	N-arallyl-n'-aralkyl piperazine pharmaceutical compositions
EP0633777B1 (de)	1998-10-14	PArENTERALE LÖSUNGEN ENTHALTEND 3-DIALKYLAMINOETHOXYBENZOYLBENZOFURANE
CN102665713A (zh)	2012-09-12	治疗心房颤动的方法
US12396970B2 (en)	2025-08-26	Anti-arrhythmic compositions and methods
JP4708648B2 (ja)	2011-06-22	レボシメンダンの医薬溶液
RU2213560C2 (ru)	2003-10-10	Фармацевтическая композиция, содержащая сочетание правовращающего и левовращающего изомеров соталола
US9125877B2 (en)	2015-09-08	Use of kauranes compounds in the manufacture of medicament
US6083991A (en)	2000-07-04	Anti-arrhythmic composition and methods of treatment
EP1121930A1 (de)	2001-08-08	Verwendung des pharmazeutischen präparates "histochrome" zur behandlung des akuten herzinfarkts und ischämischer herzerkrankungen
US8664267B2 (en)	2014-03-04	Parenteral solution containing amiodarone in NNDMA (N,N,-Dimethylacetamide)
CA2320627C (en)	2007-10-30	Medicament for treatment of diastolic dysfunction
JPH04338328A (ja)	1992-11-25	血管形成阻害剤として有用なベンゾイルカルビノール及びそのエステル
US4320110A (en)	1982-03-16	Carnitine and its use in reducing cardiac toxicity and as a synergist with cytostats
US6103757A (en)	2000-08-15	Methods for treating arrhythmia using acetate buffer solutions of amiodarone
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Frishman et al.	1988	Ultra-short-acting β-adrenergic blockers
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HU204700B (en)	1992-02-28	Process for producing aqueous compositions comprising piperidinyl cyclopentylheptenoic acid derivatives
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