CA1149388A - Encainide n-oxide - Google Patents
Encainide n-oxideInfo
- Publication number
- CA1149388A CA1149388A CA000378529A CA378529A CA1149388A CA 1149388 A CA1149388 A CA 1149388A CA 000378529 A CA000378529 A CA 000378529A CA 378529 A CA378529 A CA 378529A CA 1149388 A CA1149388 A CA 1149388A
- Authority
- CA
- Canada
- Prior art keywords
- oxide
- ethyl
- piperidyl
- benzamide
- methoxy
- Prior art date
- 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
Links
- PJWPNDMDCLXCOM-UHFFFAOYSA-N encainide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=CC=CC=C1CCC1N(C)CCCC1 PJWPNDMDCLXCOM-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 229960001142 encainide Drugs 0.000 title abstract description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- -1 compound 4-methoxy-N-[2-[2-(1-methyl-2-piperidyl)ethyl]phenyl]-benzamide N-oxide Chemical class 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 5
- 231100000419 toxicity Toxicity 0.000 abstract description 3
- 230000001988 toxicity Effects 0.000 abstract description 3
- 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 abstract 1
- 239000003416 antiarrhythmic agent Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 241000282472 Canis lupus familiaris Species 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 208000008457 Neurologic Manifestations Diseases 0.000 description 1
- 241001387976 Pera Species 0.000 description 1
- 240000001987 Pyrus communis Species 0.000 description 1
- 241000906446 Theraps Species 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
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 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
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960001952 metrifonate Drugs 0.000 description 1
- 230000007971 neurological deficit Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- IOVGROKTTNBUGK-SJCJKPOMSA-N ritodrine Chemical compound N([C@@H](C)[C@H](O)C=1C=CC(O)=CC=1)CCC1=CC=C(O)C=C1 IOVGROKTTNBUGK-SJCJKPOMSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 230000002861 ventricular Effects 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)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/160,900 US4306069A (en) | 1980-06-19 | 1980-06-19 | Encainide N-oxide |
| US160,900 | 1980-06-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1149388A true CA1149388A (en) | 1983-07-05 |
Family
ID=22578951
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000378529A Expired CA1149388A (en) | 1980-06-19 | 1981-05-28 | Encainide n-oxide |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4306069A (enExample) |
| JP (1) | JPS5756459A (enExample) |
| AT (1) | AT376422B (enExample) |
| AU (1) | AU525564B2 (enExample) |
| BE (1) | BE889309A (enExample) |
| CA (1) | CA1149388A (enExample) |
| CH (1) | CH647761A5 (enExample) |
| CY (1) | CY1363A (enExample) |
| DE (1) | DE3123942C2 (enExample) |
| DK (1) | DK152671C (enExample) |
| ES (1) | ES8300704A1 (enExample) |
| FI (1) | FI65060C (enExample) |
| FR (1) | FR2485007B1 (enExample) |
| GB (1) | GB2078729B (enExample) |
| GR (1) | GR74526B (enExample) |
| HK (1) | HK49687A (enExample) |
| IE (1) | IE51307B1 (enExample) |
| IT (1) | IT1143202B (enExample) |
| KE (1) | KE3702A (enExample) |
| LU (1) | LU83440A1 (enExample) |
| NL (1) | NL8102899A (enExample) |
| SE (1) | SE435058B (enExample) |
| SG (1) | SG22287G (enExample) |
| YU (1) | YU42239B (enExample) |
| ZA (1) | ZA813802B (enExample) |
Families Citing this family (2)
| 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 |
| JPH11513699A (ja) * | 1995-10-25 | 1999-11-24 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ルベルゾールｎ−酸化物 |
Family Cites Families (2)
| 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 YU YU1322/81A patent/YU42239B/xx unknown
- 1981-05-22 GR GR65039A patent/GR74526B/el unknown
- 1981-05-28 CA CA000378529A patent/CA1149388A/en not_active Expired
- 1981-06-05 CY CY136381A patent/CY1363A/en unknown
- 1981-06-05 GB GB8117253A patent/GB2078729B/en not_active Expired
- 1981-06-08 ZA ZA00813802A patent/ZA813802B/xx unknown
- 1981-06-15 IT IT48683/81A patent/IT1143202B/it active
- 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 FI FI811884A patent/FI65060C/fi not_active IP Right Cessation
- 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 ES ES503194A patent/ES8300704A1/es not_active Expired
- 1981-06-17 JP JP56092395A patent/JPS5756459A/ja active Granted
- 1981-06-17 SE SE8103822A patent/SE435058B/sv not_active IP Right Cessation
- 1981-06-18 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 CH CH4087/81A patent/CH647761A5/de 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
-
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
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |