CA1151067A - COMPOSITIONS PHARMACEUTIQUES ANTIARYTHMIQUES A ACTION PROLONGEE DONT LE PRINCIPE ACTIF EST 1'.alpha.-/2-/BIS (1-METHYL ETHYL) AMINO (ETHYL) .alpha.-PHENYL 2-PYRIDINE ACETAMIDEOU L'UN DE SES SELS - Google Patents
COMPOSITIONS PHARMACEUTIQUES ANTIARYTHMIQUES A ACTION PROLONGEE DONT LE PRINCIPE ACTIF EST 1'.alpha.-/2-/BIS (1-METHYL ETHYL) AMINO (ETHYL) .alpha.-PHENYL 2-PYRIDINE ACETAMIDEOU L'UN DE SES SELSInfo
- Publication number
- CA1151067A CA1151067A CA000367273A CA367273A CA1151067A CA 1151067 A CA1151067 A CA 1151067A CA 000367273 A CA000367273 A CA 000367273A CA 367273 A CA367273 A CA 367273A CA 1151067 A CA1151067 A CA 1151067A
- Authority
- CA
- Canada
- Prior art keywords
- alpha
- ethyl
- phenyl
- amino
- bis
- 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
- 239000003416 antiarrhythmic agent Substances 0.000 title claims abstract description 6
- 150000003839 salts Chemical class 0.000 title claims abstract description 6
- -1 1-METHYLETHYL Chemical class 0.000 title claims description 13
- 239000004480 active ingredient Substances 0.000 title description 5
- 239000000203 mixture Substances 0.000 title description 5
- 230000003288 anthiarrhythmic effect Effects 0.000 title description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 22
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 8
- 239000000194 fatty acid Substances 0.000 claims abstract description 8
- 229930195729 fatty acid Natural products 0.000 claims abstract description 8
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 150000002148 esters Chemical class 0.000 claims abstract description 7
- 239000000945 filler Substances 0.000 claims abstract description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 3
- 150000007524 organic acids Chemical class 0.000 claims abstract description 3
- 235000005985 organic acids Nutrition 0.000 claims abstract description 3
- 239000003814 drug Substances 0.000 claims description 18
- 229940079593 drug Drugs 0.000 claims description 17
- 229910019142 PO4 Inorganic materials 0.000 claims description 7
- 125000003976 glyceryl group Chemical group [H]C([*])([H])C(O[H])([H])C(O[H])([H])[H] 0.000 claims description 7
- 239000010452 phosphate Substances 0.000 claims description 7
- 239000000314 lubricant Substances 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 6
- 239000001267 polyvinylpyrrolidone Substances 0.000 claims description 5
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 claims description 5
- 229930006000 Sucrose Natural products 0.000 claims description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 3
- 239000011707 mineral Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 239000005720 sucrose Substances 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 2
- 230000003000 nontoxic effect Effects 0.000 claims description 2
- 230000002035 prolonged effect Effects 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000003826 tablet Substances 0.000 description 9
- 239000002775 capsule Substances 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 5
- 229960001066 disopyramide Drugs 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- UVTNFZQICZKOEM-UHFFFAOYSA-N disopyramide Chemical compound C=1C=CC=NC=1C(C(N)=O)(CCN(C(C)C)C(C)C)C1=CC=CC=C1 UVTNFZQICZKOEM-UHFFFAOYSA-N 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 239000008103 glucose Substances 0.000 description 3
- 229940075507 glyceryl monostearate Drugs 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 206010003119 arrhythmia Diseases 0.000 description 2
- 230000006793 arrhythmia Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
- 230000007775 late Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 230000036470 plasma concentration Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- UXVCEKRAZBZVSL-UHFFFAOYSA-N 2-pyridin-2-ylacetamide Chemical compound NC(=O)CC1=CC=CC=N1 UXVCEKRAZBZVSL-UHFFFAOYSA-N 0.000 description 1
- 241000238876 Acari Species 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000978776 Senegalia senegal Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical class [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000002763 arrhythmic effect Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000001746 atrial effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- ILLHQJIJCRNRCJ-UHFFFAOYSA-N dec-1-yne Chemical compound CCCCCCCCC#C ILLHQJIJCRNRCJ-UHFFFAOYSA-N 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 229960001863 disopyramide phosphate Drugs 0.000 description 1
- CGDDQFMPGMYYQP-UHFFFAOYSA-N disopyramide phosphate Chemical compound OP(O)(O)=O.C=1C=CC=NC=1C(C(N)=O)(CCN(C(C)C)C(C)C)C1=CC=CC=C1 CGDDQFMPGMYYQP-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 229940088679 drug related substance Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- AFAXGSQYZLGZPG-UHFFFAOYSA-N ethanedisulfonic acid Chemical compound OS(=O)(=O)CCS(O)(=O)=O AFAXGSQYZLGZPG-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 235000021552 granulated sugar Nutrition 0.000 description 1
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 1
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 1
- UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003509 long acting drug Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 208000008510 paroxysmal tachycardia Diseases 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000005691 triesters Chemical class 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
-
- 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
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR79-31443 | 1979-12-21 | ||
| FR7931443A FR2471784A1 (fr) | 1979-12-21 | 1979-12-21 | Medicaments antiarythmiques a action prolongee dont le principe actif est le a/2-/bis (1-methylethyl) amino/ethyl/-a-phenyl-2-pyridine acetamide ou ses sels, ainsi que le procede de preparation de ces nouveaux medicaments et compositions les renfermant |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1151067A true CA1151067A (fr) | 1983-08-02 |
Family
ID=9233075
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000367273A Expired CA1151067A (fr) | 1979-12-21 | 1980-12-19 | COMPOSITIONS PHARMACEUTIQUES ANTIARYTHMIQUES A ACTION PROLONGEE DONT LE PRINCIPE ACTIF EST 1'.alpha.-/2-/BIS (1-METHYL ETHYL) AMINO (ETHYL) .alpha.-PHENYL 2-PYRIDINE ACETAMIDEOU L'UN DE SES SELS |
Country Status (13)
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1982004392A1 (fr) * | 1981-06-18 | 1982-12-23 | Uclaf Roussel | Procede de preparation de compositions pharmaceutiques a base d'(alpha)-/2-/bis (1-methylethyl) amino/ethyl(alpha)-phenyl 2-pyridine acetamide ou de l'un de ses sels |
| US4789549A (en) * | 1987-03-09 | 1988-12-06 | Warner-Lambert Company | Sustained release dosage forms |
| JPH08143450A (ja) * | 1994-11-14 | 1996-06-04 | Taiyo Yakuhin Kogyo Kk | 徐放化製剤 |
| ME02135B (me) | 2006-03-16 | 2015-04-30 | Euro Celtique Sa | Farmaceutski sferoidi |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3062720A (en) * | 1959-05-20 | 1962-11-06 | Philips Roxane | Sustained release pharmaceutical tablet |
| FR2485M (fr) * | 1961-05-17 | 1964-04-27 | Searle & Co | Nouveaux régulateurs cardiaques. |
| GB1021924A (en) * | 1962-06-22 | 1966-03-09 | Smith Kline French Lab | Improvements in or relating to method of preparing sustained release tablets |
| BE708434A (enrdf_load_stackoverflow) * | 1966-12-22 | 1968-05-02 |
-
1979
- 1979-12-21 FR FR7931443A patent/FR2471784A1/fr active Granted
-
1980
- 1980-10-30 SE SE8007640A patent/SE8007640L/ not_active Application Discontinuation
- 1980-12-12 ZA ZA00807807A patent/ZA807807B/xx unknown
- 1980-12-18 MA MA19224A patent/MA19021A1/fr unknown
- 1980-12-18 JP JP17817480A patent/JPS56118016A/ja active Granted
- 1980-12-19 AU AU65604/80A patent/AU543380B2/en not_active Ceased
- 1980-12-19 PT PT72256A patent/PT72256B/pt unknown
- 1980-12-19 NL NL8006938A patent/NL191171C/xx not_active IP Right Cessation
- 1980-12-19 GB GB8040813A patent/GB2068226B/en not_active Expired
- 1980-12-19 CA CA000367273A patent/CA1151067A/fr not_active Expired
- 1980-12-19 DE DE19803048154 patent/DE3048154A1/de active Granted
- 1980-12-19 BE BE0/203250A patent/BE886774A/fr not_active IP Right Cessation
- 1980-12-19 IT IT50423/80A patent/IT1144024B/it active Protection Beyond IP Right Term
Also Published As
| Publication number | Publication date |
|---|---|
| IT1144024B (it) | 1986-10-29 |
| DE3048154C2 (enrdf_load_stackoverflow) | 1992-03-19 |
| FR2471784A1 (fr) | 1981-06-26 |
| AU543380B2 (en) | 1985-04-18 |
| GB2068226A (en) | 1981-08-12 |
| FR2471784B1 (enrdf_load_stackoverflow) | 1982-12-17 |
| AU6560480A (en) | 1981-06-25 |
| SE8007640L (sv) | 1981-06-22 |
| ZA807807B (en) | 1982-01-27 |
| NL191171C (nl) | 1995-03-01 |
| NL191171B (nl) | 1994-10-03 |
| JPS56118016A (en) | 1981-09-16 |
| PT72256A (fr) | 1981-01-01 |
| PT72256B (fr) | 1982-07-15 |
| BE886774A (fr) | 1981-06-19 |
| JPH0141606B2 (enrdf_load_stackoverflow) | 1989-09-06 |
| GB2068226B (en) | 1984-03-21 |
| IT8050423A0 (it) | 1980-12-19 |
| NL8006938A (nl) | 1981-07-16 |
| DE3048154A1 (de) | 1981-09-03 |
| MA19021A1 (fr) | 1981-07-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |