CY1363A - Encainide n-oxide - Google Patents

Encainide n-oxide Download PDF

Info

Publication number: CY1363A
Authority: CY; Cyprus
Prior art keywords: piperidyl; methoxy; ethyl; oxide; benzamide
Prior art date: 1980-06-19

Application number

CY136381A

Other languages

English (en)

Original Assignee

Bristol Myers Co

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.)

1980-06-19

Filing date

1981-06-05

Publication date

1987-08-07

1981-06-05 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1987-08-07 Publication of CY1363A publication Critical patent/CY1363A/en

Links

229960001142 encainide Drugs 0.000 title description 18
PJWPNDMDCLXCOM-UHFFFAOYSA-N encainide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=CC=C1CCC1N(C)CCCC1 PJWPNDMDCLXCOM-UHFFFAOYSA-N 0.000 title description 12
-1 benzamide-N-oxide Chemical compound 0.000 claims description 10
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
238000000034 method Methods 0.000 claims description 6
238000005481 NMR spectroscopy Methods 0.000 claims description 5
239000003416 antiarrhythmic agent Substances 0.000 claims description 5
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 4
150000001875 compounds Chemical class 0.000 claims description 3
150000001204 N-oxides Chemical class 0.000 claims description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 2
230000003647 oxidation Effects 0.000 claims description 2
238000007254 oxidation reaction Methods 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
150000003512 tertiary amines Chemical class 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 4
238000004519 manufacturing process Methods 0.000 claims 2
230000001590 oxidative effect Effects 0.000 claims 2
VQGZPJBOFZRTLH-UHFFFAOYSA-N N-hydroxy-4-methoxy-N-[2-[2-(1-methylpiperidin-2-yl)ethyl]phenyl]benzamide Chemical compound C1=CC(OC)=CC=C1C(=O)N(O)C1=CC=CC=C1CCC1N(C)CCCC1 VQGZPJBOFZRTLH-UHFFFAOYSA-N 0.000 claims 1
125000005936 piperidyl group Chemical group 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
241000282472 Canis lupus familiaris Species 0.000 description 7
239000000203 mixture Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
230000000694 effects Effects 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
230000003288 anthiarrhythmic effect Effects 0.000 description 3
150000004682 monohydrates Chemical class 0.000 description 3
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
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 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
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 2
244000166550 Strophanthus gratus Species 0.000 description 2
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 2
229960003343 ouabain Drugs 0.000 description 2
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
LOUPRKONTZGTKE-LHHVKLHASA-N quinidine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@H]2[C@@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-LHHVKLHASA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
VTGXVUQXDHXADV-UHFFFAOYSA-N 1-methyl-1-oxidopiperidin-1-ium Chemical class C[N+]1([O-])CCCCC1 VTGXVUQXDHXADV-UHFFFAOYSA-N 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
208000008457 Neurologic Manifestations Diseases 0.000 description 1
241000906446 Theraps Species 0.000 description 1
206010047281 Ventricular arrhythmia Diseases 0.000 description 1
DDSZWBCJXDRQDU-UHFFFAOYSA-N [N].C1CCNCC1 Chemical group [N].C1CCNCC1 DDSZWBCJXDRQDU-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 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
235000019658 bitter taste Nutrition 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
150000001722 carbon compounds Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
239000012043 crude product Substances 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
231100000518 lethal Toxicity 0.000 description 1
231100000636 lethal dose Toxicity 0.000 description 1
230000001665 lethal effect Effects 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000007971 neurological deficit Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
239000000047 product Substances 0.000 description 1
229960001404 quinidine Drugs 0.000 description 1
230000029058 respiratory gaseous exchange Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000011343 solid material Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
206010047302 ventricular tachycardia Diseases 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/92—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with a hetero atom directly attached to the ring nitrogen atom
- C07D211/94—Oxygen atom, e.g. piperidine N-oxide
- 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

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

CY136381A 1980-06-19 1981-06-05 Encainide n-oxide CY1363A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/160,900 US4306069A (en)	1980-06-19	1980-06-19	Encainide N-oxide

Publications (1)

Publication Number	Publication Date
CY1363A true CY1363A (en)	1987-08-07

Family

ID=22578951

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CY136381A CY1363A (en)	1980-06-19	1981-06-05	Encainide n-oxide

Country Status (25)

Country	Link
US (1)	US4306069A (fr)
JP (1)	JPS5756459A (fr)
AT (1)	AT376422B (fr)
AU (1)	AU525564B2 (fr)
BE (1)	BE889309A (fr)
CA (1)	CA1149388A (fr)
CH (1)	CH647761A5 (fr)
CY (1)	CY1363A (fr)
DE (1)	DE3123942C2 (fr)
DK (1)	DK152671C (fr)
ES (1)	ES503194A0 (fr)
FI (1)	FI65060C (fr)
FR (1)	FR2485007B1 (fr)
GB (1)	GB2078729B (fr)
GR (1)	GR74526B (fr)
HK (1)	HK49687A (fr)
IE (1)	IE51307B1 (fr)
IT (1)	IT1143202B (fr)
KE (1)	KE3702A (fr)
LU (1)	LU83440A1 (fr)
NL (1)	NL8102899A (fr)
SE (1)	SE435058B (fr)
SG (1)	SG22287G (fr)
YU (1)	YU42239B (fr)
ZA (1)	ZA813802B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4824853A (en) *	1985-10-11	1989-04-25	Janssen Pharmaceutica N.V.	α,α-diaryl-4-aryl-4-hydroxy-1-piperidinebutanamide, N-oxides and method of treating diarrhea
CN1200122A (zh) *	1995-10-25	1998-11-25	詹森药业有限公司	鲁贝洛唑n－氧化物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US2785168A (en) *	1955-08-16	1957-03-12	Upjohn Co	Ethyl 1-methyl-4-phenylisonipecotate nu-oxides
US3931195A (en) *	1971-03-03	1976-01-06	Mead Johnson & Company	Substituted piperidines

1980
- 1980-06-19 US US06/160,900 patent/US4306069A/en not_active Expired - Lifetime
1981
- 1981-05-20 AU AU70880/81A patent/AU525564B2/en not_active Ceased
- 1981-05-22 GR GR65039A patent/GR74526B/el unknown
- 1981-05-22 YU YU1322/81A patent/YU42239B/xx unknown
- 1981-05-28 CA CA000378529A patent/CA1149388A/fr not_active Expired
- 1981-06-05 GB GB8117253A patent/GB2078729B/en not_active Expired
- 1981-06-05 CY CY136381A patent/CY1363A/en unknown
- 1981-06-08 ZA ZA00813802A patent/ZA813802B/xx unknown
- 1981-06-15 IT IT48683/81A patent/IT1143202B/it active
- 1981-06-16 FI FI811884A patent/FI65060C/fi not_active IP Right Cessation
- 1981-06-16 FR FR818111823A patent/FR2485007B1/fr not_active Expired
- 1981-06-16 NL NL8102899A patent/NL8102899A/nl not_active Application Discontinuation
- 1981-06-16 DE DE3123942A patent/DE3123942C2/de not_active Expired
- 1981-06-17 DK DK266481A patent/DK152671C/da not_active IP Right Cessation
- 1981-06-17 JP JP56092395A patent/JPS5756459A/ja active Granted
- 1981-06-17 SE SE8103822A patent/SE435058B/sv not_active IP Right Cessation
- 1981-06-17 ES ES503194A patent/ES503194A0/es active Granted
- 1981-06-18 IE IE1354/81A patent/IE51307B1/en not_active IP Right Cessation
- 1981-06-19 BE BE0/205157A patent/BE889309A/fr not_active IP Right Cessation
- 1981-06-19 AT AT0272681A patent/AT376422B/de not_active IP Right Cessation
- 1981-06-19 LU LU83440A patent/LU83440A1/fr unknown
- 1981-06-19 CH CH4087/81A patent/CH647761A5/de not_active IP Right Cessation
1987
- 1987-03-04 SG SG222/87A patent/SG22287G/en unknown
- 1987-03-21 KE KE3702A patent/KE3702A/xx unknown
- 1987-06-25 HK HK496/87A patent/HK49687A/xx unknown

Also Published As

Publication number	Publication date
FR2485007A1 (fr)	1981-12-24
SE8103822L (sv)	1981-12-20
CH647761A5 (de)	1985-02-15
AU525564B2 (en)	1982-11-11
GR74526B (fr)	1984-06-29
ZA813802B (en)	1982-06-30
FI811884L (fi)	1981-12-20
JPS5756459A (en)	1982-04-05
CA1149388A (fr)	1983-07-05
GB2078729B (en)	1984-07-11
SE435058B (sv)	1984-09-03
NL8102899A (nl)	1982-01-18
YU42239B (en)	1988-06-30
LU83440A1 (fr)	1982-04-14
KE3702A (en)	1987-03-27
JPS6124390B2 (fr)	1986-06-10
ES8300704A1 (es)	1982-11-01
DK152671B (da)	1988-04-11
BE889309A (fr)	1981-12-21
AU7088081A (en)	1981-12-24
DE3123942C2 (de)	1986-08-28
IT8148683A0 (it)	1981-06-15
FI65060B (fi)	1983-11-30
US4306069A (en)	1981-12-15
HK49687A (en)	1987-07-03
GB2078729A (en)	1982-01-13
IT1143202B (it)	1986-10-22
DE3123942A1 (de)	1982-07-22
IE51307B1 (en)	1986-11-26
SG22287G (en)	1987-07-03
DK152671C (da)	1988-08-22
DK266481A (da)	1981-12-20
ES503194A0 (es)	1982-11-01
FR2485007B1 (fr)	1985-07-26
YU132281A (en)	1984-02-29
IE811354L (en)	1981-12-19
ATA272681A (de)	1984-04-15
AT376422B (de)	1984-11-26
FI65060C (fi)	1984-03-12

Publication	Publication Date	Title
US3900481A (en)	1975-08-19	Derivatives of pyrrolidine and piperidine
DE69704679T2 (de)	2001-09-13	4-phenylpiperidin-derivate
DK156717B (da)	1989-09-25	Analogifremgangsmaade til fremstilling af indomethacinderivater
US2567245A (en)	1951-09-11	Aryl-(2-pyridyl)-amino alkanes and their production
EP0749425A1 (fr)	1996-12-27	Nouveaux derives piperazines, leurs procedes de preparation, et compositions les contenant
CA1086735A (fr)	1980-09-30	Piperidino-quinazolines
DE2711655C2 (fr)	1987-07-16
Fries et al.	1986	Synthesis and toxicity toward nigrostriatal dopamine neurons of 1-methyl-4-phenyl-1, 2, 3, 6-tetrahydropyridine (MPTP) analogs
US3574221A (en)	1971-04-06	Derivatives of aminoalkyl pyridines
US3872113A (en)	1975-03-18	Hydroxy- and acetoxy-phthalaldehydric acid, O-(substituted) oximes
GB1567958A (en)	1980-05-21	Piperazine and piperazine homologue derivatives and preparation and use thereof
US4306069A (en)	1981-12-15	Encainide N-oxide
US3629266A (en)	1971-12-21	(phenyl piperidino alkyl)3 4-dihydrocarbostyrils
Da Re et al.	1972	. beta.-Adrenergic blocking agents of the chromone and xanthone groups. II. Propanolol type derivatives
CA1123852A (fr)	1982-05-18	Derives de cyclododecane, et methode de preparation
CA1071203A (fr)	1980-02-05	Amidines aromatiques employees comme agent antiviral chez les animaux
US3810986A (en)	1974-05-14	Novel method and composition
JPS5825678B2 (ja)	1983-05-28	オキサゾ−ルユウドウタイノセイゾウホウ
US4755601A (en)	1988-07-05	Nonyl prenyl-N heterocyclics
US4212980A (en)	1980-07-15	5-Phenoxy-2-pyridinecarbonitrile compounds and methods for their production
US3056792A (en)	1962-10-02	Unsymmetrical 1, 3-diamino-2-propanols
IE52420B1 (en)	1987-10-28	Quaternary piperidinium halides
GB2068963A (en)	1981-08-19	Basic ethers of 4-hydroxy-benzophenones acting as beta-blocking agents and relevant preparation processes
US3052679A (en)	1962-09-04	Heterocyclicaminoalkyl ethers of
US3398144A (en)	1968-08-20	Substituted 3-amino-2'-hydroxyacrylophenones