DD280965A5 - Verfahren zur herstellung von antiarrhythmisch wirkenden mitteln - Google Patents

Verfahren zur herstellung von antiarrhythmisch wirkenden mitteln Download PDF

Info

Publication number: DD280965A5
Authority: DD; German Democratic Republic
Prior art keywords: benzazepine; tetrahydro; formula; vacuo; ethyl
Prior art date: 1987-03-25

Application number

DD88313961A

Other languages

German (de)

English (en)

Inventor

Peter E Cross

John E Arrowsmith

Original Assignee

��@��k��

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.)

1987-03-25

Filing date

1988-03-24

Publication date

1990-07-25

1988-03-24 Application filed by ��@��k�� filed Critical ��@��k��

1990-07-25 Publication of DD280965A5 publication Critical patent/DD280965A5/de

Links

238000000034 method Methods 0.000 title claims description 18
238000004519 manufacturing process Methods 0.000 title description 19
239000013543 active substance Substances 0.000 title 1
150000003839 salts Chemical class 0.000 claims abstract description 14
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
229910052799 carbon Inorganic materials 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 56
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 22
-1 4-aminophenoxy-ethyl Chemical group 0.000 claims description 20
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 16
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 claims description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 11
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 10
239000012359 Methanesulfonyl chloride Substances 0.000 claims description 9
229910000027 potassium carbonate Inorganic materials 0.000 claims description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 7
235000017557 sodium bicarbonate Nutrition 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
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239000003416 antiarrhythmic agent Substances 0.000 abstract description 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 39
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VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 16
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
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239000000047 product Substances 0.000 description 12
239000012267 brine Substances 0.000 description 11
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 11
238000002360 preparation method Methods 0.000 description 10
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239000012298 atmosphere Substances 0.000 description 4
239000000284 extract Substances 0.000 description 4
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MWVMYAWMFTVYED-UHFFFAOYSA-N 2,3,4,5-tetrahydro-1h-3-benzazepine Chemical compound C1CNCCC2=CC=CC=C21 MWVMYAWMFTVYED-UHFFFAOYSA-N 0.000 description 3
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
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230000006793 arrhythmia Effects 0.000 description 3
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
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DQFQCHIDRBIESA-UHFFFAOYSA-N 1-benzazepine Chemical compound N1C=CC=CC2=CC=CC=C12 DQFQCHIDRBIESA-UHFFFAOYSA-N 0.000 description 2
SEWGFZSRLNWBEY-UHFFFAOYSA-N 2-azidoethyl methanesulfonate Chemical compound CS(=O)(=O)OCCN=[N+]=[N-] SEWGFZSRLNWBEY-UHFFFAOYSA-N 0.000 description 2
DJDAPLBWGIXUAG-UHFFFAOYSA-N 2-methoxy-4-nitrobenzoyl chloride Chemical compound COC1=CC([N+]([O-])=O)=CC=C1C(Cl)=O DJDAPLBWGIXUAG-UHFFFAOYSA-N 0.000 description 2
OUQOZFWVBMZDQB-UHFFFAOYSA-N 3-(2-azidoethyl)-7-nitro-1,2,4,5-tetrahydro-3-benzazepine Chemical compound C1CN(CCN=[N+]=[N-])CCC2=CC([N+](=O)[O-])=CC=C21 OUQOZFWVBMZDQB-UHFFFAOYSA-N 0.000 description 2
206010003658 Atrial Fibrillation Diseases 0.000 description 2
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206010042600 Supraventricular arrhythmias Diseases 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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230000010933 acylation Effects 0.000 description 2
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YIWGJFPJRAEKMK-UHFFFAOYSA-N 1-(2H-benzotriazol-5-yl)-3-methyl-8-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carbonyl]-1,3,8-triazaspiro[4.5]decane-2,4-dione Chemical compound CN1C(=O)N(c2ccc3n[nH]nc3c2)C2(CCN(CC2)C(=O)c2cnc(NCc3cccc(OC(F)(F)F)c3)nc2)C1=O YIWGJFPJRAEKMK-UHFFFAOYSA-N 0.000 description 1
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210000004165 myocardium Anatomy 0.000 description 1
230000000926 neurological effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
210000003540 papillary muscle Anatomy 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
230000000644 propagated effect Effects 0.000 description 1
230000001902 propagating effect Effects 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
206010037844 rash Diseases 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
230000033764 rhythmic process Effects 0.000 description 1
210000005241 right ventricle Anatomy 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000004088 simulation Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000003860 storage Methods 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
PNIRXSPRJRSPJH-UHFFFAOYSA-N tert-butyl 7-amino-1,2,4,5-tetrahydro-3-benzazepine-3-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC2=CC=C(N)C=C21 PNIRXSPRJRSPJH-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
- 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
- C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
- C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D233/16—Radicals substituted by nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Heart & Thoracic Surgery (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Plural Heterocyclic Compounds (AREA)
Other In-Based Heterocyclic Compounds (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)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Saccharide Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Apparatus For Radiation Diagnosis (AREA)
Diaphragms For Electromechanical Transducers (AREA)
Magnetic Resonance Imaging Apparatus (AREA)

DD88313961A 1987-03-25 1988-03-24 Verfahren zur herstellung von antiarrhythmisch wirkenden mitteln DD280965A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB878707120A GB8707120D0 (en)	1987-03-25	1987-03-25	Antiarrhythmic agents

Publications (1)

Publication Number	Publication Date
DD280965A5 true DD280965A5 (de)	1990-07-25

Family

ID=10614606

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88313961A DD280965A5 (de)	1987-03-25	1988-03-24	Verfahren zur herstellung von antiarrhythmisch wirkenden mitteln

Country Status (28)

Country	Link
US (1)	US4891372A (es)
EP (1)	EP0284384B1 (es)
JP (1)	JPH0662573B2 (es)
KR (1)	KR900006099B1 (es)
CN (1)	CN1023644C (es)
AT (1)	ATE58726T1 (es)
AU (1)	AU583763B2 (es)
CA (1)	CA1294273C (es)
DD (1)	DD280965A5 (es)
DE (1)	DE3861147D1 (es)
DK (1)	DK170890B1 (es)
ES (1)	ES2021142B3 (es)
FI (1)	FI85468C (es)
GB (1)	GB8707120D0 (es)
GR (1)	GR3001507T3 (es)
HU (1)	HU199124B (es)
IE (1)	IE61070B1 (es)
IL (1)	IL85822A (es)
MX (1)	MX10867A (es)
MY (1)	MY103245A (es)
NO (1)	NO168421C (es)
NZ (1)	NZ224017A (es)
PH (1)	PH24074A (es)
PL (1)	PL153455B1 (es)
PT (1)	PT87048B (es)
SU (1)	SU1579456A3 (es)
YU (1)	YU47191B (es)
ZA (1)	ZA882103B (es)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4906634A (en) *	1988-03-08	1990-03-06	Schering A.G.	Novel N-[4-(aminosubstituted)phenyl]methanesulfonamides and their use as cardiovascular agents
US4966967A (en) *	1989-09-15	1990-10-30	Berlex Laboratories, Inc.	3,4,5,6-tetrahydro-2H-1,7,4-benzodioxazonines as cardiovascular agents
US5112824A (en) *	1989-12-08	1992-05-12	Merck & Co., Inc.	Benzofuran compounds as class III antiarrhythmic agents
US5032604A (en) *	1989-12-08	1991-07-16	Merck & Co., Inc.	Class III antiarrhythmic agents
US5206240A (en) *	1989-12-08	1993-04-27	Merck & Co., Inc.	Nitrogen-containing spirocycles
US5215989A (en) *	1989-12-08	1993-06-01	Merck & Co., Inc.	Nitrogen-containing heterocyclic compounds as class III antiarrhythmic agents
US5032598A (en) *	1989-12-08	1991-07-16	Merck & Co., Inc.	Nitrogens containing heterocyclic compounds as class III antiarrhythmic agents
US5382587A (en) *	1993-06-30	1995-01-17	Merck & Co., Inc.	Spirocycles
US5403846A (en) *	1993-11-22	1995-04-04	Merck & Co., Inc.	Spirocycles
US5439914A (en) *	1994-02-18	1995-08-08	Merck & Co., Inc.	Spirocycles
US6083991A (en)	1997-06-04	2000-07-04	University Of Florida Research Foundation, Inc.	Anti-arrhythmic composition and methods of treatment
FR2920773B1 (fr) *	2007-09-11	2009-10-23	Servier Lab	Derives de 1,2,4,5-tetrahydro-3h-benzazepines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3478149A (en) *	1962-01-24	1969-11-11	Mead Johnson & Co	Therapeutic compositions and methods employing sulfonamidophenethanolamines
FR148F (es) *	1962-01-24
US4233217A (en) *	1968-03-11	1980-11-11	Pennwalt Corporation	Substituted 1,2,4,5-tetrahydro-3H, 3 benzazepines
CA974989A (en) *	1968-03-11	1975-09-23	Wallace And Tiernan Inc.	Process for preparing 1,2,4,5-tetrahydro-3h,3-benzazepines and products obtained thereby
US3758692A (en) *	1969-04-14	1973-09-11	Mead Johnson & Co	Ylamines sympathomimetic process and compositions employing sulfonamidophenalk
US3574741A (en) *	1969-04-14	1971-04-13	Mead Johnson & Co	Sulfonamidophenalkylamines
BE757005A (fr) *	1969-10-02	1971-04-02	Bristol Myers Co	Phenethanolamines substituees et procede pour leur preparation
US4210749A (en) *	1974-11-12	1980-07-01	Pennwalt Corporation	Substituted 1,2,4,5-tetrahydro-3H,3 benzazepines
US4581370A (en) *	1983-07-12	1986-04-08	Schering A.G.	Antiarrhythmic imidazoliums
EP0164865B1 (en) *	1984-05-04	1988-12-21	The Upjohn Company	N-(aminoalkylphenyl)sulfonamides their preparation and therapeutic use
DK180485D0 (da) *	1985-04-22	1985-04-23	Novo Industri As	Nitrogenholdige forbindelser
EP0204349A3 (de) *	1985-06-01	1990-01-03	Dr. Karl Thomae GmbH	Neue heteroaromatische Aminderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung

1987
- 1987-03-25 GB GB878707120A patent/GB8707120D0/en active Pending
1988
- 1988-03-21 US US07/170,499 patent/US4891372A/en not_active Expired - Lifetime
- 1988-03-22 MY MYPI88000297A patent/MY103245A/en unknown
- 1988-03-23 PL PL1988271379A patent/PL153455B1/pl unknown
- 1988-03-23 CA CA000562151A patent/CA1294273C/en not_active Expired - Lifetime
- 1988-03-23 IL IL85822A patent/IL85822A/xx not_active IP Right Cessation
- 1988-03-23 PT PT87048A patent/PT87048B/pt not_active IP Right Cessation
- 1988-03-23 FI FI881392A patent/FI85468C/fi not_active IP Right Cessation
- 1988-03-24 YU YU59688A patent/YU47191B/sh unknown
- 1988-03-24 SU SU4355570A patent/SU1579456A3/ru active
- 1988-03-24 DE DE8888302597T patent/DE3861147D1/de not_active Expired - Lifetime
- 1988-03-24 ES ES88302597T patent/ES2021142B3/es not_active Expired - Lifetime
- 1988-03-24 PH PH36682A patent/PH24074A/en unknown
- 1988-03-24 EP EP88302597A patent/EP0284384B1/en not_active Expired - Lifetime
- 1988-03-24 KR KR1019880003152A patent/KR900006099B1/ko not_active Expired
- 1988-03-24 MX MX1086788A patent/MX10867A/es unknown
- 1988-03-24 DD DD88313961A patent/DD280965A5/de not_active IP Right Cessation
- 1988-03-24 DK DK160488A patent/DK170890B1/da not_active IP Right Cessation
- 1988-03-24 AT AT88302597T patent/ATE58726T1/de not_active IP Right Cessation
- 1988-03-24 NZ NZ224017A patent/NZ224017A/xx unknown
- 1988-03-24 ZA ZA882103A patent/ZA882103B/xx unknown
- 1988-03-24 AU AU13571/88A patent/AU583763B2/en not_active Ceased
- 1988-03-24 NO NO881314A patent/NO168421C/no not_active IP Right Cessation
- 1988-03-24 IE IE88488A patent/IE61070B1/en not_active IP Right Cessation
- 1988-03-25 CN CN88101782A patent/CN1023644C/zh not_active Expired - Fee Related
- 1988-03-25 JP JP63071710A patent/JPH0662573B2/ja not_active Expired - Fee Related
- 1988-03-25 HU HU881530A patent/HU199124B/hu not_active IP Right Cessation
1991
- 1991-02-26 GR GR91400225T patent/GR3001507T3/el unknown

Also Published As

Publication number	Publication date
GB8707120D0 (en)	1987-04-29
ES2021142B3 (es)	1991-10-16
EP0284384A1 (en)	1988-09-28
DK160488D0 (da)	1988-03-24
NO168421C (no)	1992-02-19
YU47191B (sh)	1995-01-31
AU583763B2 (en)	1989-05-04
KR880011112A (ko)	1988-10-26
EP0284384B1 (en)	1990-11-28
IL85822A (en)	1992-03-29
CN88101782A (zh)	1988-11-02
HU199124B (en)	1990-01-29
IL85822A0 (en)	1988-09-30
DK170890B1 (da)	1996-03-04
IE880884L (en)	1988-09-25
PH24074A (en)	1990-03-05
KR900006099B1 (ko)	1990-08-22
DE3861147D1 (de)	1991-01-10
CA1294273C (en)	1992-01-14
GR3001507T3 (en)	1992-11-23
YU59688A (en)	1991-04-30
MX10867A (es)	1993-09-01
SU1579456A3 (ru)	1990-07-15
ATE58726T1 (de)	1990-12-15
FI881392A0 (fi)	1988-03-23
FI85468C (fi)	1992-04-27
NO881314D0 (no)	1988-03-24
PT87048B (pt)	1992-07-31
PT87048A (pt)	1988-04-01
FI881392A7 (fi)	1988-09-26
US4891372A (en)	1990-01-02
DK160488A (da)	1988-12-30
MY103245A (en)	1993-05-29
PL271379A1 (en)	1988-12-22
IE61070B1 (en)	1994-09-21
ZA882103B (en)	1989-11-29
AU1357188A (en)	1988-09-29
NO168421B (no)	1991-11-11
CN1023644C (zh)	1994-02-02
NO881314L (no)	1988-09-26
FI85468B (fi)	1992-01-15
PL153455B1 (en)	1991-04-30
JPS63255267A (ja)	1988-10-21
HUT47544A (en)	1989-03-28
NZ224017A (en)	1990-06-26
JPH0662573B2 (ja)	1994-08-17

Legal Events

Date	Code	Title	Description
1996-05-09	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
AT363096B (de)	1981-07-10	Verfahren zur herstellung von neuen phthalazinderivaten und deren salzen
DE3852551T2 (de)	1995-05-18	Amine und deren verwendung.
DD205904A5 (de)	1984-01-11	Verfahren zur herstellung von imidazo (4,5-c) pyridin-derivaten
DE60102473T2 (de)	2005-02-03	Indolochinazolinone
AT399338B (de)	1995-04-25	Neue substituierte benzamide, verfahren zu ihrer herstellung und pharmazeutische zusammensetzungen, die diese benzamide enthalten
DE2707048C2 (de)	1983-11-17	2-Alkyl-3-Benzoyl-Indolizinderivate, Verfahren zu deren Herstellung, sowie diese enthaltende Zusammensetzungen
DE3034001A1 (de)	1982-04-22	Isochinolinderivate, verfahren zu ihrer hersellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung
DE19824175A1 (de)	1999-12-02	Amino-azol-Verbindungen
DE2363052A1 (de)	1974-07-11	3-phenyl-3-aminoalkyl-2,6-dioxo-tetraund -hexahydropyridine, verfahren zu ihrer herstellung und ihre verwendung in pharmazeutischen zubereitungen
DD281596A5 (de)	1990-08-15	Verfahren zur hersteung antiarrhytmischer mittel
DE69720021T2 (de)	2004-02-05	1,4-disubstituierte piperazine
US4891372A (en)	1990-01-02	Antiarrhythmic agents, compositions and method of use thereas
DE2426149B2 (de)	1980-01-31	7-Fluor-substituierte Phenothiazine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Mittel
CH650783A5 (de)	1985-08-15	Carbostyrilderivate, verfahren zu deren herstellung und arzneimittel, welche diese enthalten.
EP0254955B1 (de)	1992-05-27	Substituierte Pyrido-[2,3-b][1,4]benzodiazepin-6-one, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel
DE2821584C2 (es)	1992-01-02
DE3424586A1 (de)	1986-01-09	3-aminocarbonylmethoxy-5-phenyl-pyrazol-verbindungen sowie verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
DE69022442T2 (de)	1996-05-09	Aminoalkoxyphenyl-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende Zusammensetzungen.
CH616934A5 (en)	1980-04-30	Process for the preparation of chromone derivatives
EP0285323B1 (en)	1990-11-28	Antiarrhythmic agents
DE2406065A1 (de)	1974-08-15	Neue isoindolinderivate, ihre herstellung und die zusammensetzungen, die sie enthalten
CH642367A5 (de)	1984-04-13	Imidazo-isochinolin-dione.
DE3874465T2 (de)	1993-02-25	1,2,3,4-tetrahydroisochonoline als antiarrhythmische mittel.
DE2221808C2 (de)	1985-06-20	Hydrazinopyridazin-Derivate, deren Säureadditionssalze, Verfahren zu deren Herstellung und Heilmittel
DE1076691B (de)	1960-03-03	Verfahren zur Herstellung von Phenthiazinderivaten