NL8202840A - Antiaritmische fenethylpiperidineverbindingen. - Google Patents
Antiaritmische fenethylpiperidineverbindingen. Download PDFInfo
- Publication number
- NL8202840A NL8202840A NL8202840A NL8202840A NL8202840A NL 8202840 A NL8202840 A NL 8202840A NL 8202840 A NL8202840 A NL 8202840A NL 8202840 A NL8202840 A NL 8202840A NL 8202840 A NL8202840 A NL 8202840A
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- NL
- Netherlands
- Prior art keywords
- formula
- compounds
- ethyl
- methyl
- acid
- Prior art date
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- DBDVAKGHPZJLTH-UHFFFAOYSA-N 1-(2-phenylethyl)piperidine Chemical class C1CCCCN1CCC1=CC=CC=C1 DBDVAKGHPZJLTH-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 39
- -1 2-piperidinyl Chemical group 0.000 claims description 19
- 230000003288 anthiarrhythmic effect Effects 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- GWEHVDNNLFDJLR-UHFFFAOYSA-N 1,3-diphenylurea Chemical compound C=1C=CC=CC=1NC(=O)NC1=CC=CC=C1 GWEHVDNNLFDJLR-UHFFFAOYSA-N 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 150000002540 isothiocyanates Chemical class 0.000 claims description 4
- 238000010992 reflux Methods 0.000 claims description 4
- 238000007327 hydrogenolysis reaction Methods 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
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- ICUOYYCLRPMKDC-UHFFFAOYSA-N 1-(2-phenylethyl)piperidin-2-amine Chemical compound NC1CCCCN1CCC1=CC=CC=C1 ICUOYYCLRPMKDC-UHFFFAOYSA-N 0.000 description 3
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- CCXFKJBMYLLRBW-UHFFFAOYSA-N 2-[2-(1-methylpiperidin-2-yl)ethyl]aniline Chemical compound CN1CCCCC1CCC1=CC=CC=C1N CCXFKJBMYLLRBW-UHFFFAOYSA-N 0.000 description 3
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 210000003516 pericardium Anatomy 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 210000000689 upper leg Anatomy 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 239000008096 xylene Substances 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
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28371081 | 1981-07-16 | ||
| US06/283,710 US4399286A (en) | 1981-07-16 | 1981-07-16 | Antiarrhythmic phenethylpiperidine compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8202840A true NL8202840A (nl) | 1983-02-16 |
Family
ID=23087221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8202840A NL8202840A (nl) | 1981-07-16 | 1982-07-13 | Antiaritmische fenethylpiperidineverbindingen. |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4399286A (ko) |
| JP (1) | JPS6059230B2 (ko) |
| KR (1) | KR860000516B1 (ko) |
| AR (1) | AR231720A1 (ko) |
| AU (1) | AU559967B2 (ko) |
| BE (1) | BE893862A (ko) |
| CA (1) | CA1192199A (ko) |
| CH (1) | CH654575A5 (ko) |
| CY (1) | CY1375A (ko) |
| DE (1) | DE3226540A1 (ko) |
| DK (1) | DK316882A (ko) |
| ES (1) | ES8307748A1 (ko) |
| FR (1) | FR2510568B1 (ko) |
| GB (1) | GB2104889B (ko) |
| GR (1) | GR76173B (ko) |
| HK (1) | HK4988A (ko) |
| IE (1) | IE53546B1 (ko) |
| IT (1) | IT1149020B (ko) |
| KE (1) | KE3719A (ko) |
| LU (1) | LU84278A1 (ko) |
| NL (1) | NL8202840A (ko) |
| PT (1) | PT75259B (ko) |
| SG (1) | SG29887G (ko) |
| YU (1) | YU44095B (ko) |
| ZA (1) | ZA824487B (ko) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2531702A1 (fr) * | 1982-08-16 | 1984-02-17 | Synthelabo | Derives de phenethyl-1a-phenylperidine-3-propanenitrile, leur preparation et leur application en therapeutique |
| AU2978197A (en) * | 1996-06-04 | 1998-01-05 | Chugai Seiyaku Kabushiki Kaisha | Substituted benzenes having nos inhibitory effects |
| DE10132746A1 (de) * | 2001-07-05 | 2003-02-06 | Gruenenthal Gmbh | Substituierte 1-Phenethylpiperidinverbindungen |
| US7635548B2 (en) * | 2006-08-08 | 2009-12-22 | Xerox Corporation | Photoreceptor |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2626948A (en) * | 1950-07-24 | 1953-01-27 | Hoffmann La Roche | 1-alkyl-2 or 4-[(n-alkyl-n-beta-dialkyl-aminoalkyl) aminophenethyl]-piperidines and salts thereof |
| CA979009A (en) | 1968-09-16 | 1975-12-02 | Squibb (E. R.) And Sons | Substituted ureas and derivatives |
| US3852339A (en) * | 1970-06-15 | 1974-12-03 | Squibb & Sons Inc | Aminoalkoxyphenylurea derivatives |
| CA961038A (en) * | 1971-03-03 | 1975-01-14 | Joseph L. Minielli | Substituted piperidines |
| US4000143A (en) * | 1971-03-03 | 1976-12-28 | Mead Johnson & Company | Substituted piperidines |
| US4064254A (en) * | 1971-03-03 | 1977-12-20 | Mead Johnson & Company | Substituted piperidines therapeutic process and compositions |
| US3931195A (en) * | 1971-03-03 | 1976-01-06 | Mead Johnson & Company | Substituted piperidines |
| US4007181A (en) * | 1974-02-11 | 1977-02-08 | The Upjohn Company | Adamantyl containing guanidines |
| GB1459506A (en) * | 1974-02-18 | 1976-12-22 | Wyeth John & Brother Ltd | Piperidine derivatives |
| US4096276A (en) * | 1976-04-15 | 1978-06-20 | Hoffmann-La Roche Inc. | Thiourea derivatives for treating hypertension |
| US4071524A (en) * | 1976-11-08 | 1978-01-31 | Riker Laboratories, Inc. | Derivatives of urea |
-
1981
- 1981-07-16 US US06/283,710 patent/US4399286A/en not_active Expired - Fee Related
-
1982
- 1982-06-24 ZA ZA824487A patent/ZA824487B/xx unknown
- 1982-07-01 FR FR8211563A patent/FR2510568B1/fr not_active Expired
- 1982-07-02 GB GB08219237A patent/GB2104889B/en not_active Expired
- 1982-07-02 CY CY137582A patent/CY1375A/xx unknown
- 1982-07-05 CA CA000406583A patent/CA1192199A/en not_active Expired
- 1982-07-06 AU AU85660/82A patent/AU559967B2/en not_active Ceased
- 1982-07-08 AR AR289934A patent/AR231720A1/es active
- 1982-07-09 ES ES513832A patent/ES8307748A1/es not_active Expired
- 1982-07-12 IT IT48796/82A patent/IT1149020B/it active
- 1982-07-13 KR KR8203124A patent/KR860000516B1/ko active
- 1982-07-13 GR GR68742A patent/GR76173B/el unknown
- 1982-07-13 NL NL8202840A patent/NL8202840A/nl not_active Application Discontinuation
- 1982-07-14 DK DK316882A patent/DK316882A/da not_active Application Discontinuation
- 1982-07-15 CH CH4319/82A patent/CH654575A5/de not_active IP Right Cessation
- 1982-07-15 JP JP57123737A patent/JPS6059230B2/ja not_active Expired
- 1982-07-15 PT PT75259A patent/PT75259B/pt not_active IP Right Cessation
- 1982-07-15 IE IE1710/82A patent/IE53546B1/en unknown
- 1982-07-15 YU YU1543/82A patent/YU44095B/xx unknown
- 1982-07-15 DE DE19823226540 patent/DE3226540A1/de active Granted
- 1982-07-16 LU LU84278A patent/LU84278A1/fr unknown
- 1982-07-16 BE BE0/208612A patent/BE893862A/fr not_active IP Right Cessation
-
1987
- 1987-03-27 SG SG298/87A patent/SG29887G/en unknown
- 1987-03-31 KE KE3719A patent/KE3719A/xx unknown
-
1988
- 1988-01-21 HK HK49/88A patent/HK4988A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CY1375A (en) | 1987-08-07 |
| GB2104889B (en) | 1985-05-22 |
| AR231720A1 (es) | 1985-02-28 |
| SG29887G (en) | 1987-07-17 |
| AU559967B2 (en) | 1987-03-26 |
| DE3226540C2 (ko) | 1990-04-12 |
| KR860000516B1 (ko) | 1986-05-02 |
| AU8566082A (en) | 1983-01-20 |
| HK4988A (en) | 1988-01-29 |
| GR76173B (ko) | 1984-08-03 |
| ES513832A0 (es) | 1983-08-01 |
| IT8248796A0 (it) | 1982-07-12 |
| KR840000492A (ko) | 1984-02-22 |
| FR2510568B1 (fr) | 1985-09-27 |
| CA1192199A (en) | 1985-08-20 |
| CH654575A5 (de) | 1986-02-28 |
| PT75259A (en) | 1982-08-01 |
| PT75259B (en) | 1985-10-04 |
| JPS5865276A (ja) | 1983-04-18 |
| YU154382A (en) | 1985-04-30 |
| IT1149020B (it) | 1986-12-03 |
| BE893862A (fr) | 1983-01-17 |
| US4399286A (en) | 1983-08-16 |
| GB2104889A (en) | 1983-03-16 |
| IE53546B1 (en) | 1988-12-07 |
| DK316882A (da) | 1983-01-17 |
| LU84278A1 (fr) | 1983-04-13 |
| DE3226540A1 (de) | 1983-02-03 |
| ES8307748A1 (es) | 1983-08-01 |
| YU44095B (en) | 1990-02-28 |
| KE3719A (en) | 1987-04-16 |
| FR2510568A1 (fr) | 1983-02-04 |
| JPS6059230B2 (ja) | 1985-12-24 |
| ZA824487B (en) | 1983-04-27 |
| IE821710L (en) | 1983-01-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1A | A request for search or an international-type search has been filed | ||
| BB | A search report has been drawn up | ||
| A85 | Still pending on 85-01-01 | ||
| BC | A request for examination has been filed | ||
| DNT | Communications of changes of names of applicants whose applications have been laid open to public inspection |
Free format text: BRISTOL-MYERS SQUIBB COMPANY |
|
| BV | The patent application has lapsed |