AP50A - Improvements in pharmaceutially acceptable salts. - Google Patents
Improvements in pharmaceutially acceptable salts. Download PDFInfo
- Publication number
- AP50A AP50A APAP/P/1987/000060A AP8700060A AP50A AP 50 A AP50 A AP 50A AP 8700060 A AP8700060 A AP 8700060A AP 50 A AP50 A AP 50A
- Authority
- AP
- ARIPO
- Prior art keywords
- amlodipine
- salt
- solution
- besylate
- steps
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 41
- HTIQEAQVCYTUBX-UHFFFAOYSA-N amlodipine Chemical class CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl HTIQEAQVCYTUBX-UHFFFAOYSA-N 0.000 claims abstract description 45
- 229960000528 amlodipine Drugs 0.000 claims abstract description 43
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical class [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 claims abstract description 33
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 19
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 239000000243 solution Substances 0.000 claims description 14
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims description 12
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 239000011928 denatured alcohol Substances 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 8
- 239000007864 aqueous solution Substances 0.000 claims description 7
- 239000007916 tablet composition Substances 0.000 claims description 7
- 229920000168 Microcrystalline cellulose Polymers 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 239000002775 capsule Substances 0.000 claims description 6
- 239000007963 capsule composition Substances 0.000 claims description 6
- 235000019359 magnesium stearate Nutrition 0.000 claims description 6
- 235000019813 microcrystalline cellulose Nutrition 0.000 claims description 6
- 239000008108 microcrystalline cellulose Substances 0.000 claims description 6
- 229940016286 microcrystalline cellulose Drugs 0.000 claims description 6
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 claims description 5
- 238000007906 compression Methods 0.000 claims description 5
- 230000006835 compression Effects 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000008215 water for injection Substances 0.000 claims description 5
- 229920002261 Corn starch Polymers 0.000 claims description 4
- 235000019759 Maize starch Nutrition 0.000 claims description 4
- 239000001913 cellulose Substances 0.000 claims description 4
- 235000010980 cellulose Nutrition 0.000 claims description 4
- 229920002678 cellulose Polymers 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 239000000314 lubricant Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229940080313 sodium starch Drugs 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 230000000996 additive effect Effects 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 239000007884 disintegrant Substances 0.000 claims description 2
- 239000003701 inert diluent Substances 0.000 claims description 2
- 230000001954 sterilising effect Effects 0.000 claims description 2
- 238000007873 sieving Methods 0.000 claims 5
- 238000003825 pressing Methods 0.000 claims 2
- 239000008365 aqueous carrier Substances 0.000 claims 1
- 239000000645 desinfectant Substances 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 208000019622 heart disease Diseases 0.000 claims 1
- 239000008174 sterile solution Substances 0.000 claims 1
- 230000002253 anti-ischaemic effect Effects 0.000 abstract description 2
- 229940030600 antihypertensive agent Drugs 0.000 abstract description 2
- 239000002220 antihypertensive agent Substances 0.000 abstract description 2
- 238000009472 formulation Methods 0.000 description 10
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 230000015556 catabolic process Effects 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- -1 2-aminoethoxymethyl Chemical group 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 2
- 229960001860 salicylate Drugs 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- VOPNAHNLWOLODK-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;phenylmethanesulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.OS(=O)(=O)CC1=CC=CC=C1 VOPNAHNLWOLODK-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 229940127291 Calcium channel antagonist Drugs 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 206010018910 Haemolysis Diseases 0.000 description 1
- 101000713879 Homo sapiens T-complex protein 1 subunit eta Proteins 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 102100036476 T-complex protein 1 subunit eta Human genes 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- ZPBWCRDSRKPIDG-UHFFFAOYSA-N amlodipine benzenesulfonate Chemical compound OS(=O)(=O)C1=CC=CC=C1.CCOC(=O)C1=C(COCCN)NC(C)=C(C(=O)OC)C1C1=CC=CC=C1Cl ZPBWCRDSRKPIDG-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000181 anti-adherent effect Effects 0.000 description 1
- 239000003911 antiadherent Substances 0.000 description 1
- WWLOCCUNZXBJFR-UHFFFAOYSA-N azanium;benzenesulfonate Chemical compound [NH4+].[O-]S(=O)(=O)C1=CC=CC=C1 WWLOCCUNZXBJFR-UHFFFAOYSA-N 0.000 description 1
- WWIWLTSSHDKOKO-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1.OS(=O)(=O)C1=CC=CC=C1 WWIWLTSSHDKOKO-UHFFFAOYSA-N 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000000480 calcium channel blocker Substances 0.000 description 1
- PASHVRUKOFIRIK-UHFFFAOYSA-L calcium sulfate dihydrate Chemical compound O.O.[Ca+2].[O-]S([O-])(=O)=O PASHVRUKOFIRIK-UHFFFAOYSA-L 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229940050411 fumarate Drugs 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 230000008588 hemolysis Effects 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- JIEMQHXUDSJROH-UHFFFAOYSA-M sodium;propane-1,2-diol;chloride Chemical compound [Na+].[Cl-].CC(O)CO JIEMQHXUDSJROH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
Classifications
-
- 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
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4866—Organic macromolecular compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
- A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
-
- 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
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- 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
- A61K9/2009—Inorganic compounds
-
- 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
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2054—Cellulose; Cellulose derivatives, e.g. hydroxypropyl methylcellulose
-
- 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
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07D211/80—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 two double bonds between ring members or between ring members and non-ring members
- C07D211/84—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 two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen directly attached to ring carbon atoms
- C07D211/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- A61K9/2022—Organic macromolecular compounds
- A61K9/205—Polysaccharides, e.g. alginate, gums; Cyclodextrin
- A61K9/2059—Starch, including chemically or physically modified derivatives; Amylose; Amylopectin; Dextrin
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Inorganic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB868608335A GB8608335D0 (en) | 1986-04-04 | 1986-04-04 | Pharmaceutically acceptable salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AP8700060A0 AP8700060A0 (en) | 1987-02-01 |
| AP50A true AP50A (en) | 1989-09-16 |
Family
ID=10595731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| APAP/P/1987/000060A AP50A (en) | 1986-04-04 | 1987-04-02 | Improvements in pharmaceutially acceptable salts. |
Country Status (47)
Families Citing this family (172)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5270323A (en) * | 1990-05-31 | 1993-12-14 | Pfizer Inc. | Method of treating impotence |
| CA2124445A1 (en) * | 1991-11-26 | 1993-06-10 | James W. Young | Methods and compositions for treating hypertension, angina and other disorders using optically pure (-) amlodipine |
| US6057344A (en) | 1991-11-26 | 2000-05-02 | Sepracor, Inc. | Methods for treating hypertension, and angina using optically pure (-) amlodipine |
| US6162802A (en) * | 1992-03-10 | 2000-12-19 | Papa; Joseph | Synergistic combination therapy using benazepril and amlodipine for the treatment of cardiovascular disorders and compositions therefor |
| AT399718B (de) * | 1992-04-16 | 1995-07-25 | Lek Tovarna Farmacevtskih | Inklusionskomplexe von optisch aktiven und racemischen 1,4-dihydropyridinen mit methyl-beta- cyclodextrin oder anderen cyclodextrinderivaten, ein verfahren zur herstellung von optisch aktiven dihydropyridinen und deren inklusionskomplexen und diese komplexe enthaltende pharmazeutische formulierungen |
| US5389654A (en) * | 1992-11-26 | 1995-02-14 | Lek, Tovarna, Farmacevtskih In Kemicnih . . . | 3-ethyl 5-methyl(±)2-[2-(N-tritylamino)ethoxymethyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-6-methyl-3,5-pyridinedicarboxylate |
| SI9200344B (sl) * | 1992-11-26 | 1998-06-30 | Lek, | Postopek za pripravo amlodipin benzensulfonata |
| USRE39384E1 (en) | 1993-09-01 | 2006-11-07 | Smithkline Beecham P.L.C. | Substituted thiazolidinedione derivatives |
| US6221335B1 (en) * | 1994-03-25 | 2001-04-24 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| US6245787B1 (en) | 1995-03-16 | 2001-06-12 | Pfizer Inc. | Composition containing amlodipine or a pharmaceutically acceptable salt thereof, and an ACE inhibitor |
| HU221810B1 (hu) * | 1997-08-12 | 2003-01-28 | EGIS Gyógyszergyár Rt. | Eljárás amlodipin-bezilát előállítására és az eljárás intermedierjei |
| GT199800127A (es) * | 1997-08-29 | 2000-02-01 | Combinaciones terapeuticas. | |
| WO1999018957A1 (en) * | 1998-03-26 | 1999-04-22 | Reddy-Cheminor, Inc. | Stable pharmaceutical composition containing amlodipine besylate and atenolol |
| RU2188636C2 (ru) * | 1998-03-26 | 2002-09-10 | Др. Редди'С Лабораторис Лтд. | Стабильный фармацевтический препарат, содержащий амлодипина безилат и атенолол |
| PL189666B1 (pl) * | 1998-04-09 | 2005-09-30 | Adamed Sp Z Oo | Sposób otrzymywania benzenosulfonianu amlodypiny |
| SI2322174T1 (sl) | 1998-07-10 | 2015-12-31 | Novartis Pharma Ag | Kombinirana uporaba valsartana in blokatorjev kalcijevih kanalov za terapevtske namene |
| US7772220B2 (en) * | 2004-10-15 | 2010-08-10 | Seo Hong Yoo | Methods and compositions for reducing toxicity of a pharmaceutical compound |
| US7303768B2 (en) * | 1998-07-24 | 2007-12-04 | Seo Hong Yoo | Preparation of aqueous clear solution dosage forms with bile acids |
| US20070072828A1 (en) * | 1998-07-24 | 2007-03-29 | Yoo Seo H | Bile preparations for colorectal disorders |
| US20050158408A1 (en) * | 1998-07-24 | 2005-07-21 | Yoo Seo H. | Dried forms of aqueous solubilized bile acid dosage formulation: preparation and uses thereof |
| UA33033A (uk) * | 1998-10-16 | 2001-02-15 | Др.Редіс Леборетрис Лтд | Спосіб одержання безилату амлодипіну |
| US7129265B2 (en) * | 1999-04-23 | 2006-10-31 | Mason R Preston | Synergistic effects of amlodipine and atorvastatin metabolite as a basis for combination therapy |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0060674A1 (en) * | 1981-03-14 | 1982-09-22 | Pfizer Limited | Dihydropyridine anti-ischaemic and antihypertensive agents, processes for their production, and pharmaceutical compositions containing them |
| EP0089167A2 (en) * | 1982-03-11 | 1983-09-21 | Pfizer Limited | Dihydropyridine anti-ischaemic and antihypertensive agents, processes for their production, and pharmaceutical compositions containing them |
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| US3816612A (en) * | 1967-03-23 | 1974-06-11 | Degussa | Process for the production of basically reacting pharmaceuticals |
| US4032637A (en) * | 1972-09-26 | 1977-06-28 | Sandoz Ltd. | Method of promoting sleep |
| US4177278A (en) * | 1977-04-05 | 1979-12-04 | Bayer Aktiengesellschaft | 2-Alkyleneaminodihydropyridines compounds, their production and their medicinal use |
| JPS5547656A (en) * | 1978-09-29 | 1980-04-04 | Dainippon Pharmaceut Co Ltd | 2-(2-substituted aminoethyl)-1,4-dihydropyridine derivative and its derivative |
| ZA839187B (en) * | 1982-12-10 | 1984-07-25 | Ciba Geigy Ag | Amide compounds |
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1986
- 1986-04-04 GB GB868608335A patent/GB8608335D0/en active Pending
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1987
- 1987-03-18 LU LU86812A patent/LU86812A1/fr unknown
- 1987-03-30 CN CN87102493A patent/CN1023800C/zh not_active Expired - Lifetime
- 1987-03-30 DE DE19873710457 patent/DE3710457A1/de not_active Withdrawn
- 1987-03-31 ES ES87302767T patent/ES2012803B3/es not_active Expired - Lifetime
- 1987-03-31 EG EG191/87A patent/EG18266A/xx active
- 1987-03-31 GB GB8707653A patent/GB2188630B/en not_active Expired - Lifetime
- 1987-03-31 EP EP87302767A patent/EP0244944B1/en not_active Expired - Lifetime
- 1987-03-31 DE DE8787302767T patent/DE3761485D1/de not_active Expired - Lifetime
- 1987-03-31 AT AT87302767T patent/ATE49752T1/de not_active IP Right Cessation
- 1987-03-31 SE SE8701348A patent/SE463457B/sv not_active IP Right Cessation
- 1987-04-01 MY MYPI87000413A patent/MY101177A/en unknown
- 1987-04-01 MX MX584787A patent/MX5847A/es unknown
- 1987-04-02 AP APAP/P/1987/000060A patent/AP50A/en active
- 1987-04-02 CA CA000533732A patent/CA1321393C/en not_active Expired - Lifetime
- 1987-04-02 CS CS872363A patent/CS265237B2/cs not_active IP Right Cessation
- 1987-04-02 AR AR87307197A patent/AR242562A1/es active
- 1987-04-02 PT PT84611A patent/PT84611B/pt unknown
- 1987-04-02 GR GR870525A patent/GR870525B/el unknown
- 1987-04-02 YU YU580/87A patent/YU44801B/xx unknown
- 1987-04-02 IN IN281/DEL/87A patent/IN168414B/en unknown
- 1987-04-02 PH PH35098A patent/PH24348A/en unknown
- 1987-04-03 JP JP62082787A patent/JPS62240660A/ja active Granted
- 1987-04-03 IL IL82101A patent/IL82101A/xx not_active IP Right Cessation
- 1987-04-03 IT IT19977/87A patent/IT1203853B/it active
- 1987-04-03 BE BE8700349A patent/BE1000130A4/fr not_active IP Right Cessation
- 1987-04-03 UA UA4202353A patent/UA6344A1/uk unknown
- 1987-04-03 SU SU874202353A patent/SU1498388A3/ru active
- 1987-04-03 ES ES8700965A patent/ES2002599A6/es not_active Expired
- 1987-04-03 NZ NZ219868A patent/NZ219868A/xx unknown
- 1987-04-03 HU HU871450A patent/HU196962B/hu unknown
- 1987-04-03 DK DK170187A patent/DK171708B1/da active IP Right Grant
- 1987-04-03 FR FR8704705A patent/FR2596758B1/fr not_active Expired
- 1987-04-03 DD DD87301485A patent/DD265142A5/de unknown
- 1987-04-03 IE IE86987A patent/IE59457B1/en not_active IP Right Cessation
- 1987-04-03 NO NO871408A patent/NO172181C/no unknown
- 1987-04-03 ZA ZA872439A patent/ZA872439B/xx unknown
- 1987-04-03 FI FI871470A patent/FI85017C/fi not_active IP Right Cessation
- 1987-04-03 NL NL8700791A patent/NL8700791A/nl not_active Application Discontinuation
- 1987-04-03 PL PL1987264982A patent/PL149532B1/pl unknown
- 1987-04-03 MA MA21175A patent/MA20938A1/fr unknown
- 1987-04-04 KR KR1019870003209A patent/KR950006710B1/ko not_active Expired - Lifetime
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1988
- 1988-10-13 US US07/256,938 patent/US4879303A/en not_active Expired - Lifetime
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1990
- 1990-03-21 GR GR90400158T patent/GR3000394T3/el unknown
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1991
- 1991-11-22 SK SK3539-91A patent/SK278435B6/sk unknown
- 1991-11-22 CZ CS19913539A patent/CZ289095B6/cs not_active IP Right Cessation
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1992
- 1992-03-16 BG BG096073A patent/BG60698B2/xx unknown
- 1992-06-04 SG SG596/92A patent/SG59692G/en unknown
- 1992-10-01 HK HK760/92A patent/HK76092A/en not_active IP Right Cessation
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1993
- 1993-05-14 CY CY1669A patent/CY1669A/xx unknown
-
1994
- 1994-07-26 EC EC1994001129A patent/ECSP941129A/es unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0060674A1 (en) * | 1981-03-14 | 1982-09-22 | Pfizer Limited | Dihydropyridine anti-ischaemic and antihypertensive agents, processes for their production, and pharmaceutical compositions containing them |
| EP0089167A2 (en) * | 1982-03-11 | 1983-09-21 | Pfizer Limited | Dihydropyridine anti-ischaemic and antihypertensive agents, processes for their production, and pharmaceutical compositions containing them |
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