CA1107734A - Antiarrhythmic quinuclidine carboxylic acid xylidide and method of producing the same and similar compounds - Google Patents

Antiarrhythmic quinuclidine carboxylic acid xylidide and method of producing the same and similar compounds

Info

Publication number: CA1107734A
Authority: CA; Canada
Prior art keywords: carboxylic acid; quinuclidine; compound; antiarrhythmic; xylidide
Prior art date: 1977-01-19
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.): Expired

Application number

CA295,163A

Other languages

English (en)

French (fr)

Inventor

Edna Oppenheimer

Eliezer Kaplinsky

Sasson Cohen

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.)

Purdue Frederick Co Canada Ltd

Original Assignee

Purdue Frederick Co Canada Ltd

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.)

1977-01-19

Filing date

1978-01-18

Publication date

1981-08-25

1978-01-18 Application filed by Purdue Frederick Co Canada Ltd filed Critical Purdue Frederick Co Canada Ltd

1981-08-25 Application granted granted Critical

1981-08-25 Publication of CA1107734A publication Critical patent/CA1107734A/en

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 46
238000000034 method Methods 0.000 title claims abstract description 22
LIUAALCHBQSCCX-UHFFFAOYSA-N 1-azoniabicyclo[2.2.2]octane-2-carboxylate Chemical compound C1CN2C(C(=O)O)CC1CC2 LIUAALCHBQSCCX-UHFFFAOYSA-N 0.000 title claims abstract description 17
230000003288 anthiarrhythmic effect Effects 0.000 title abstract description 13
239000003416 antiarrhythmic agent Substances 0.000 title abstract description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 20
PUIHXLMMFNAYNW-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octane-3-carboxylic acid Chemical compound C1CC2C(C(=O)O)CN1CC2 PUIHXLMMFNAYNW-UHFFFAOYSA-N 0.000 claims abstract description 9
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 14
UFFBMTHBGFGIHF-UHFFFAOYSA-N 2,6-dimethylaniline Chemical group CC1=CC=CC(C)=C1N UFFBMTHBGFGIHF-UHFFFAOYSA-N 0.000 claims description 12
238000006243 chemical reaction Methods 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
150000002431 hydrogen Chemical class 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
MANJIGKYCYWWBD-UHFFFAOYSA-N 2-chloro-2-oxoacetic acid Chemical compound OC(=O)C(Cl)=O MANJIGKYCYWWBD-UHFFFAOYSA-N 0.000 claims description 2
238000010992 reflux Methods 0.000 claims description 2
150000001448 anilines Chemical class 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract description 12
238000004519 manufacturing process Methods 0.000 abstract description 7
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract description 6
150000003839 salts Chemical class 0.000 abstract description 5
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 abstract 1
206010003119 arrhythmia Diseases 0.000 description 28
230000006793 arrhythmia Effects 0.000 description 27
230000000694 effects Effects 0.000 description 24
206010047302 ventricular tachycardia Diseases 0.000 description 14
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 13
241000282472 Canis lupus familiaris Species 0.000 description 13
NNJVILVZKWQKPM-UHFFFAOYSA-N Lidocaine Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1C NNJVILVZKWQKPM-UHFFFAOYSA-N 0.000 description 13
229960004194 lidocaine Drugs 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 8
239000002253 acid Substances 0.000 description 8
229960001701 chloroform Drugs 0.000 description 8
229940079593 drug Drugs 0.000 description 8
239000003814 drug Substances 0.000 description 8
238000011282 treatment Methods 0.000 description 8
241000282326 Felis catus Species 0.000 description 7
241001465754 Metazoa Species 0.000 description 7
229940105631 nembutal Drugs 0.000 description 7
230000033764 rhythmic process Effects 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
239000000203 mixture Substances 0.000 description 6
LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 6
239000000243 solution Substances 0.000 description 6
238000012360 testing method Methods 0.000 description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
LPMXVESGRSUGHW-UHFFFAOYSA-N Acolongiflorosid K Natural products OC1C(O)C(O)C(C)OC1OC1CC2(O)CCC3C4(O)CCC(C=5COC(=O)C=5)C4(C)CC(O)C3C2(CO)C(O)C1 LPMXVESGRSUGHW-UHFFFAOYSA-N 0.000 description 5
LPMXVESGRSUGHW-GHYGWZAOSA-N Ouabain Natural products O([C@@H]1[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O1)[C@H]1C[C@@H](O)[C@@]2(CO)[C@@](O)(C1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)C[C@@H](O)[C@H]21 LPMXVESGRSUGHW-GHYGWZAOSA-N 0.000 description 5
244000166550 Strophanthus gratus Species 0.000 description 5
230000001186 cumulative effect Effects 0.000 description 5
238000001802 infusion Methods 0.000 description 5
238000010253 intravenous injection Methods 0.000 description 5
229960003343 ouabain Drugs 0.000 description 5
239000008280 blood Substances 0.000 description 4
210000004369 blood Anatomy 0.000 description 4
238000009826 distribution Methods 0.000 description 4
238000007912 intraperitoneal administration Methods 0.000 description 4
238000001990 intravenous administration Methods 0.000 description 4
HCIRLKXASKPUHN-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-1-azabicyclo[2.2.2]octane-3-carboxamide Chemical compound CC1=CC=CC(C)=C1NC(=O)C1C(CC2)CCN2C1 HCIRLKXASKPUHN-UHFFFAOYSA-N 0.000 description 4
230000000144 pharmacologic effect Effects 0.000 description 4
SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
206010010904 Convulsion Diseases 0.000 description 3
241000699670 Mus sp. Species 0.000 description 3
CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 3
230000008859 change Effects 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
238000002347 injection Methods 0.000 description 3
239000007924 injection Substances 0.000 description 3
231100000189 neurotoxic Toxicity 0.000 description 3
230000002887 neurotoxic effect Effects 0.000 description 3
239000002904 solvent Substances 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
238000011287 therapeutic dose Methods 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
206010015856 Extrasystoles Diseases 0.000 description 2
208000001953 Hypotension Diseases 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
206010029350 Neurotoxicity Diseases 0.000 description 2
RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 2
208000000418 Premature Cardiac Complexes Diseases 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
206010044221 Toxic encephalopathy Diseases 0.000 description 2
230000003444 anaesthetic effect Effects 0.000 description 2
230000002763 arrhythmic effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
230000036765 blood level Effects 0.000 description 2
230000036772 blood pressure Effects 0.000 description 2
230000037396 body weight Effects 0.000 description 2
230000000747 cardiac effect Effects 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
210000004351 coronary vessel Anatomy 0.000 description 2
238000003379 elimination reaction Methods 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
230000037406 food intake Effects 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
238000007429 general method Methods 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
230000036543 hypotension Effects 0.000 description 2
239000000463 material Substances 0.000 description 2
150000004702 methyl esters Chemical class 0.000 description 2
231100000228 neurotoxicity Toxicity 0.000 description 2
230000007135 neurotoxicity Effects 0.000 description 2
239000012264 purified product Substances 0.000 description 2
230000029058 respiratory gaseous exchange Effects 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
230000000638 stimulation Effects 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
230000002861 ventricular Effects 0.000 description 2
-1 xalyl chloride Chemical compound 0.000 description 2
GNLJBJNONOOOQC-UHFFFAOYSA-N $l^{3}-carbane;magnesium Chemical compound [Mg]C GNLJBJNONOOOQC-UHFFFAOYSA-N 0.000 description 1
JOIJZJVAIURHGA-UHFFFAOYSA-N 1-azabicyclo[2.2.2]octane-2-carboxylic acid;hydrochloride Chemical compound Cl.C1CN2C(C(=O)O)CC1CC2 JOIJZJVAIURHGA-UHFFFAOYSA-N 0.000 description 1
206010003591 Ataxia Diseases 0.000 description 1
206010003671 Atrioventricular Block Diseases 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
241000725101 Clea Species 0.000 description 1
208000001778 Coronary Occlusion Diseases 0.000 description 1
206010011086 Coronary artery occlusion Diseases 0.000 description 1
206010033799 Paralysis Diseases 0.000 description 1
208000004756 Respiratory Insufficiency Diseases 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
206010042434 Sudden death Diseases 0.000 description 1
206010070863 Toxicity to various agents Diseases 0.000 description 1
206010044565 Tremor Diseases 0.000 description 1
206010047700 Vomiting Diseases 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
210000001367 artery Anatomy 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
229910001919 chlorite Inorganic materials 0.000 description 1
229910052619 chlorite group Inorganic materials 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
230000036461 convulsion Effects 0.000 description 1
230000000875 corresponding effect Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
210000001105 femoral artery Anatomy 0.000 description 1
210000003191 femoral vein Anatomy 0.000 description 1
KGPPDNUWZNWPSI-UHFFFAOYSA-N flurotyl Chemical compound FC(F)(F)COCC(F)(F)F KGPPDNUWZNWPSI-UHFFFAOYSA-N 0.000 description 1
239000012458 free base Substances 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
230000006872 improvement Effects 0.000 description 1
230000006698 induction Effects 0.000 description 1
230000003993 interaction Effects 0.000 description 1
229950003188 isovaleryl diethylamide Drugs 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
VXWPONVCMVLXBW-UHFFFAOYSA-M magnesium;carbanide;iodide Chemical compound [CH3-].[Mg+2].[I-] VXWPONVCMVLXBW-UHFFFAOYSA-M 0.000 description 1
238000005259 measurement Methods 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
230000002906 microbiologic effect Effects 0.000 description 1
230000036651 mood Effects 0.000 description 1
230000002107 myocardial effect Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
230000036470 plasma concentration Effects 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000008569 process Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
238000011321 prophylaxis Methods 0.000 description 1
238000000718 qrs complex Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
201000004193 respiratory failure Diseases 0.000 description 1
201000002932 second-degree atrioventricular block Diseases 0.000 description 1
230000035939 shock Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000008279 sol Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000001629 suppression Effects 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
231100001274 therapeutic index Toxicity 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
210000003437 trachea Anatomy 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
208000003663 ventricular fibrillation Diseases 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- 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

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pyrrole Compounds (AREA)

CA295,163A 1977-01-19 1978-01-18 Antiarrhythmic quinuclidine carboxylic acid xylidide and method of producing the same and similar compounds Expired CA1107734A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
IL51296A IL51296A (en)	1977-01-19	1977-01-19	Antiarrhythmic composition comprising a quinuclidine-3-carboxylic acid anilide and novel method for the preparation of such anilides
IL51296		1977-01-19

Publications (1)

Publication Number	Publication Date
CA1107734A true CA1107734A (en)	1981-08-25

Family

ID=11049358

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA295,163A Expired CA1107734A (en)	1977-01-19	1978-01-18	Antiarrhythmic quinuclidine carboxylic acid xylidide and method of producing the same and similar compounds

Country Status (16)

Country	Link
JP (1)	JPS53109952A (de)
AT (1)	AT355586B (de)
AU (1)	AU519089B2 (de)
CA (1)	CA1107734A (de)
DE (1)	DE2802208A1 (de)
DK (1)	DK147180C (de)
ES (1)	ES465827A1 (de)
FI (1)	FI773923A7 (de)
FR (1)	FR2384499A1 (de)
GB (2)	GB1578422A (de)
IL (1)	IL51296A (de)
NO (1)	NO148335C (de)
NZ (1)	NZ185904A (de)
PT (1)	PT67401B (de)
SE (1)	SE443786B (de)
ZA (1)	ZA777476B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE10211416A1 (de)	2002-03-15	2003-09-25	Bayer Ag	Essig- und Propionsäureamide

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
SE331841B (de) *	1967-05-23	1971-01-18	Astra Ab

1977
- 1977-01-19 IL IL51296A patent/IL51296A/xx unknown
- 1977-12-08 NZ NZ185904A patent/NZ185904A/en unknown
- 1977-12-14 PT PT67401A patent/PT67401B/pt unknown
- 1977-12-15 ZA ZA00777476A patent/ZA777476B/xx unknown
- 1977-12-23 FI FI773923A patent/FI773923A7/fi not_active Application Discontinuation
1978
- 1978-01-07 ES ES465827A patent/ES465827A1/es not_active Expired
- 1978-01-09 SE SE7800204A patent/SE443786B/sv unknown
- 1978-01-17 AU AU32489/78A patent/AU519089B2/en not_active Expired
- 1978-01-18 CA CA295,163A patent/CA1107734A/en not_active Expired
- 1978-01-18 NO NO780177A patent/NO148335C/no unknown
- 1978-01-18 AT AT35378A patent/AT355586B/de not_active IP Right Cessation
- 1978-01-18 FR FR7801354A patent/FR2384499A1/fr active Granted
- 1978-01-18 DK DK26478A patent/DK147180C/da active
- 1978-01-19 DE DE19782802208 patent/DE2802208A1/de not_active Withdrawn
- 1978-01-19 JP JP476478A patent/JPS53109952A/ja active Granted
- 1978-01-19 GB GB21014/79A patent/GB1578422A/en not_active Expired
- 1978-01-19 GB GB2197/78A patent/GB1578421A/en not_active Expired

Also Published As

Publication number	Publication date
AU3248978A (en)	1979-07-26
GB1578421A (en)	1980-11-05
JPS53109952A (en)	1978-09-26
NO780177L (no)	1978-07-20
PT67401B (en)	1979-05-21
AT355586B (de)	1980-03-10
NO148335B (no)	1983-06-13
AU519089B2 (en)	1981-11-05
IL51296A (en)	1983-10-31
SE7800204L (sv)	1978-07-20
NZ185904A (en)	1984-05-31
SE443786B (sv)	1986-03-10
NO148335C (no)	1983-09-21
ES465827A1 (es)	1979-01-01
GB1578422A (en)	1980-11-05
FR2384499A1 (fr)	1978-10-20
ATA35378A (de)	1979-08-15
FR2384499B1 (de)	1981-10-30
DK147180B (da)	1984-05-07
IL51296A0 (en)	1977-03-31
JPS638111B2 (de)	1988-02-19
FI773923A7 (fi)	1978-07-20
DK26478A (da)	1978-07-20
ZA777476B (en)	1978-10-25
DK147180C (da)	1984-11-12
PT67401A (en)	1978-01-01
DE2802208A1 (de)	1978-07-20

Legal Events

Date	Code	Title	Description
1998-08-25	MKEX	Expiry

Publication	Publication Date	Title
JPS6135178B2 (de)	1986-08-12
DE4321306A1 (de)	1995-01-05	Disulfide
EP0600949A1 (de)	1994-06-15	Neue 3,5-di-tert.butyl-4-hydroxyphenyl-derivate, verfahren zu ihrer herstellung und arzneimittel.
EP0384279B1 (de)	1994-04-13	Benzolsulfonamide und Verfahren zu ihrer Herstellung
CH642955A5 (de)	1984-05-15	Thiazole, verwendung derselben und diese enthaltende arzneimittel.
US4831054A (en)	1989-05-16	2-Alkyl-3-benzoylbenzofurans useful for treating cardiac arrhythmia
US4011330A (en)	1977-03-08	Vincaminic acid amides
CA1107734A (en)	1981-08-25	Antiarrhythmic quinuclidine carboxylic acid xylidide and method of producing the same and similar compounds
DE3787844T2 (de)	1994-02-10	Thioester und dessen Verwendung zur Herstellung von pharmazeutischen Zusammensetzungen zur Behandlung von Ischämie und von Reperfusion-Syndromen.
DE3107743A1 (de)	1981-12-03	Neue klasse von acylderivaten des carnitins, verfahren zu deren herstellung sowie ihre therapeutische verwendung
DE2941288A1 (de)	1980-04-30	Cystein-derivate
US4146628A (en)	1979-03-27	Antiarrhythmic quinuclidine carboxylic acid xylidide and method of producing the same and similar compounds
EP0105458B1 (de)	1989-11-23	Alpha-Aryl-alpha-pyridylalkanoicsäure-Derivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zusammensetzung
US4218477A (en)	1980-08-19	Primary aminoacylanilides, methods of making the same and use as antiarrhythmic drugs
EP0046143B1 (de)	1983-09-07	Lidocain-Derivate und diese als wirksamen Grundstoff enthaltende therapeutische Zusammensetzungen
US4567192A (en)	1986-01-28	Acylaminophenol derivatives
US4237068A (en)	1980-12-02	Primary aminoacylanilides
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