CS265237B2 - Process for preparing salt of 3-ethyl-5-methyl-2-/aminoethoxymethyl/4-/2-chlorphenyl/-1,4-dihydro-6-methylpyridin-3,5-dicarboxylate with benzensulphonic acid - Google Patents
Process for preparing salt of 3-ethyl-5-methyl-2-/aminoethoxymethyl/4-/2-chlorphenyl/-1,4-dihydro-6-methylpyridin-3,5-dicarboxylate with benzensulphonic acid Download PDFInfo
- Publication number
- CS265237B2 CS265237B2 CS872363A CS236387A CS265237B2 CS 265237 B2 CS265237 B2 CS 265237B2 CS 872363 A CS872363 A CS 872363A CS 236387 A CS236387 A CS 236387A CS 265237 B2 CS265237 B2 CS 265237B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- amlodipine
- besylate
- ethyl
- aminoethoxymethyl
- dicarboxylate
- Prior art date
Links
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 title claims 2
- 150000003839 salts Chemical class 0.000 title abstract description 30
- 238000004519 manufacturing process Methods 0.000 title description 4
- 238000000034 method Methods 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 239000012442 inert solvent Substances 0.000 claims description 3
- -1 3-ethyl-5-methyl-2- (2-aminoethoxymethyl) -4- (2-chlorophenyl) -1,4-dihydro-6-methylpyridin-3 benzenesulfonate Chemical compound 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 150000008107 benzenesulfonic acids Chemical class 0.000 claims description 2
- NWDQBIRZEWCIMO-UHFFFAOYSA-N 2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-3-ethyl-5,6-dimethylpiperidine-3,5-dicarboxylic acid Chemical compound CCC1(C(O)=O)C(COCCN)NC(C)C(C)(C(O)=O)C1C1=CC=CC=C1Cl NWDQBIRZEWCIMO-UHFFFAOYSA-N 0.000 claims 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical class [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 abstract description 14
- 229960000528 amlodipine Drugs 0.000 abstract description 11
- 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 abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 4
- 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
- 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 39
- 239000000203 mixture Substances 0.000 description 20
- 229960004005 amlodipine besylate Drugs 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000003826 tablet Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 9
- 239000013543 active substance Substances 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 8
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 7
- 239000002775 capsule Substances 0.000 description 7
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 7
- 239000008108 microcrystalline cellulose Substances 0.000 description 7
- 229940016286 microcrystalline cellulose Drugs 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 235000019441 ethanol Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000007906 compression Methods 0.000 description 4
- 230000006835 compression Effects 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 3
- 230000000181 anti-adherent effect Effects 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 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 3
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000008120 corn starch Substances 0.000 description 3
- 235000019700 dicalcium phosphate Nutrition 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000008215 water for injection Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 238000002144 chemical decomposition reaction 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
- 239000002904 solvent Substances 0.000 description 2
- 229940032147 starch Drugs 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 2
- BMSZNJAHQMIOMH-ODZAUARKSA-N (z)-but-2-enedioic acid;methanesulfonic acid Chemical compound CS(O)(=O)=O.OC(=O)\C=C/C(O)=O BMSZNJAHQMIOMH-ODZAUARKSA-N 0.000 description 1
- 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
- LBLYYCQCTBFVLH-UHFFFAOYSA-M 2-methylbenzenesulfonate Chemical compound CC1=CC=CC=C1S([O-])(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 206010002383 Angina Pectoris Diseases 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
- YDNKLXKFNAGQBV-VCALNXSSSA-N Cl.C(C)(=O)O.C(\C=C/C(=O)O)(=O)O.C(C=1C(O)=CC=CC1)(=O)O.C(CCC(=O)O)(=O)O.S(=O)(=O)(O)C1=CC=C(C)C=C1.S(C)(=O)(=O)O Chemical compound Cl.C(C)(=O)O.C(\C=C/C(=O)O)(=O)O.C(C=1C(O)=CC=CC1)(=O)O.C(CCC(=O)O)(=O)O.S(=O)(=O)(O)C1=CC=C(C)C=C1.S(C)(=O)(=O)O YDNKLXKFNAGQBV-VCALNXSSSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 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
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001450 anions Chemical class 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
- 239000002585 base Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 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
- 239000007963 capsule composition Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012065 filter cake Substances 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
- 239000003701 inert diluent Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- GXHMMDRXHUIUMN-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O GXHMMDRXHUIUMN-UHFFFAOYSA-N 0.000 description 1
- 150000004682 monohydrates Chemical group 0.000 description 1
- 238000000465 moulding Methods 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
- 238000007911 parenteral administration Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229940023144 sodium glycolate Drugs 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000007916 tablet composition Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 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)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Inorganic Chemistry (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)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyridine Compounds (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 |
|---|---|
| CS236387A2 CS236387A2 (en) | 1989-01-12 |
| CS265237B2 true CS265237B2 (en) | 1989-10-13 |
Family
ID=10595731
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS872363A CS265237B2 (en) | 1986-04-04 | 1987-04-02 | Process for preparing salt of 3-ethyl-5-methyl-2-/aminoethoxymethyl/4-/2-chlorphenyl/-1,4-dihydro-6-methylpyridin-3,5-dicarboxylate with benzensulphonic acid |
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 |
| US6057344A (en) | 1991-11-26 | 2000-05-02 | Sepracor, Inc. | Methods for treating hypertension, and angina using optically pure (-) amlodipine |
| WO1993010779A1 (en) * | 1991-11-26 | 1993-06-10 | Sepracor, Inc. | Methods and compositions for treating hypertension, angina and other disorders 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 |
| SI9200344B (sl) * | 1992-11-26 | 1998-06-30 | Lek, | Postopek za pripravo amlodipin benzensulfonata |
| 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 |
| 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 |
| EP0804229B1 (en) | 1995-03-16 | 2003-03-26 | Pfizer Inc. | Use of amlodipine, a salt thereof or felodipin in combination with an ace inhibitor in the manufacture of a medicament for the treatment of nonischemic congestive heart failure |
| 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. | |
| RU2188636C2 (ru) * | 1998-03-26 | 2002-09-10 | Др. Редди'С Лабораторис Лтд. | Стабильный фармацевтический препарат, содержащий амлодипина безилат и атенолол |
| AU6767198A (en) * | 1998-03-26 | 1999-05-03 | Dr. Reddy's Laboratories Limited | Stable pharmaceutical composition containing amlodipine besylate and atenol ol |
| PL189666B1 (pl) * | 1998-04-09 | 2005-09-30 | Adamed Sp Z Oo | Sposób otrzymywania benzenosulfonianu amlodypiny |
| JP2002520274A (ja) | 1998-07-10 | 2002-07-09 | ノバルティス アクチエンゲゼルシャフト | バルサルタンとカルシウムチャンネルブロッカーの抗高血圧組合わせ |
| 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 |
| US20050158408A1 (en) * | 1998-07-24 | 2005-07-21 | Yoo Seo H. | Dried forms of aqueous solubilized bile acid dosage formulation: preparation and uses thereof |
| US20070072828A1 (en) * | 1998-07-24 | 2007-03-29 | Yoo Seo H | Bile preparations for colorectal disorders |
| 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 |
| RU2142942C1 (ru) * | 1999-04-28 | 1999-12-20 | Дж. Б.Кемикалс энд Фармасьютикалс Лтд. | Способ получения монобензолсульфоната 3-этил-5-метилового эфира 2-[(2-аминоэтокси)метил]-4-(2-хлорфенил)-1,4-дигидро-6-метил-3,5-пиридинди карбоновой кислоты |
| AP2001002345A0 (en) | 1999-05-27 | 2001-12-31 | Pfizer Prod Inc | Mutual prodrugs of amlodipine and atorvastatin. |
| HN2000000050A (es) | 1999-05-27 | 2001-02-02 | Pfizer Prod Inc | Sal mutua de amlodipino y atorvastatina |
| RU2161156C1 (ru) * | 1999-06-01 | 2000-12-27 | Джи.Б.Кемикалс Энд Фармасьютикалс Лтд | Способ получения 3-этил-5-метиловый эфир 2-[2-(n-фталимидо)-этоксиметил]-4-(2-хлорфенил)-1,4-дигидро-6-метил-3,5- пиридиндикарбоновой кислоты |
| UA72768C2 (en) * | 1999-07-05 | 2005-04-15 | Richter Gedeon Vegyeszet | A method for obtaining amilodipine benzenesulphonate |
| RU2146672C1 (ru) * | 1999-10-13 | 2000-03-20 | Др.Редди'С Лабораторис Лтд. | Способ получения 3-этил-5-метил(±)2[2-аминоэтокси)-метил]-4-(2-хлорфенил)-1,4-дигидро- 6-метил-3,5-пиридиндикарбоксилат монобензолсульфоната |
| US6521647B2 (en) | 2000-04-04 | 2003-02-18 | Pfizer Inc. | Treatment of renal disorders |
| US6835742B2 (en) | 2000-08-04 | 2004-12-28 | R. Preston Mason | Synergistic effect of amlodipine and atorvastatin on cholesterol crystal formation inhibition and aortic endothelial cell nitric oxide release |
| GB0027410D0 (en) * | 2000-11-09 | 2000-12-27 | Pfizer Ltd | Mutual prodrug of amlodipine and atorvastatin |
| US6737430B2 (en) | 2000-11-09 | 2004-05-18 | Pfizer, Inc. | Mutual prodrug of amlodipine and atorvastatin |
| AT5874U1 (de) | 2000-12-29 | 2003-01-27 | Bioorg Bv | Pharmazeutische zubereitungen enthaltend amlodipinmaleat |
| US6653481B2 (en) * | 2000-12-29 | 2003-11-25 | Synthon Bv | Process for making amlodipine |
| DE60112305T2 (de) * | 2000-12-29 | 2006-05-24 | Pfizer Ltd., Sandwich | Verfahren zur herstellung amlodipinmaleat |
| WO2002053540A1 (en) * | 2000-12-29 | 2002-07-11 | Pfizer Limited | Aspartate derivative of amlodipine as calcium channel antagonist |
| WO2002053541A1 (en) | 2000-12-29 | 2002-07-11 | Pfizer Limited | Amide derivative of amlodipine |
| BR0116552A (pt) | 2000-12-29 | 2004-02-03 | Pfizer Ltd | Hemi-maleato de amlodipina, processo, método para o tratamento ou prevenção de angina ou hipertensão, composição farmacêutica, para uso no tratamento e/ou de angina ou da hipertensão |
| US7335380B2 (en) | 2000-12-29 | 2008-02-26 | Synthon Ip Inc. | Amlodipine free base |
| EP1346214A2 (en) | 2000-12-29 | 2003-09-24 | Pfizer Limited | Reference standards and processes for determining the purity or stability of amlodipine maleate |
| EP1309556B1 (en) | 2000-12-29 | 2004-11-24 | Pfizer Limited | Amlodipine fumarate |
| MXPA03005882A (es) | 2000-12-29 | 2005-04-19 | Pfizer Ltd | Derivado amida de amlodipina. |
| ATE356806T1 (de) * | 2001-01-09 | 2007-04-15 | Siegfried Generics Int Ag | Salze von amlodipin-mesylat |
| GB0103046D0 (en) | 2001-02-07 | 2001-03-21 | Novartis Ag | Organic Compounds |
| KR100452491B1 (ko) * | 2001-03-29 | 2004-10-12 | 한미약품 주식회사 | 신규한 결정형 암로디핀 캠실레이트 염 및 그의 제조방법 |
| US20030027848A1 (en) * | 2001-06-15 | 2003-02-06 | Anne Billotte | Stabilized formulations |
| US7153970B2 (en) | 2001-07-06 | 2006-12-26 | Lek Pharmaceuticals D.D. | High purity amlodipine benzenesulfonate and a process for its preparation |
| US20030220310A1 (en) * | 2001-07-27 | 2003-11-27 | Schuh Joseph R. | Epoxy-steroidal aldosterone antagonist and calcium channel blocker combination therapy for treatment of congestive heart failure |
| US6680334B2 (en) | 2001-08-28 | 2004-01-20 | Pfizer Inc | Crystalline material |
| US7544681B2 (en) | 2001-09-27 | 2009-06-09 | Ramot At Tel Aviv University Ltd. | Conjugated psychotropic drugs and uses thereof |
| US20040001886A1 (en) * | 2001-10-17 | 2004-01-01 | Dr. Reddy's Laboratories Limited | Stabilized pharmaceutical formulations containing amlodipine maleate |
| US6828339B2 (en) * | 2001-11-21 | 2004-12-07 | Synthon Bv | Amlodipine salt forms and processes for preparing them |
| HU226642B1 (en) * | 2001-12-17 | 2009-05-28 | Egis Gyogyszergyar Nyilvanosan | Amlodipine bezylate tablets having extended stability and process for producing the same |
| NL1019882C2 (nl) * | 2002-02-01 | 2003-08-04 | Synthon Licensing | Amlodipine vrije base. |
| JP4625637B2 (ja) | 2002-02-22 | 2011-02-02 | シャイア エルエルシー | 活性物質送達系及び活性物質を保護し投与する方法 |
| WO2003089414A1 (en) * | 2002-04-13 | 2003-10-30 | Hanlim Pharmaceutical Co., Ltd. | Amlodipine nicotinate and process for the preparation thereof |
| AU2003239383C1 (en) | 2002-05-06 | 2009-03-19 | Endocyte, Inc. | Vitamin-targeted imaging agents |
| EG24716A (en) | 2002-05-17 | 2010-06-07 | Novartis Ag | Combination of organic compounds |
| SI21233A (sl) * | 2002-05-31 | 2003-12-31 | LEK, tovarna farmacevtskih in kemičnih izdelkov, d.d. | Kristalni hidratni obliki amlodipin benzensulfonata visoke čistote, postopki za njuno pripravo in uporaba |
| US6699892B2 (en) | 2002-06-04 | 2004-03-02 | Yung Shin Pharmaceutical Industrial Co., Ltd. | Pharmaceutically acceptable salt of amlodipine and method of preparing the same |
| RU2221784C1 (ru) * | 2002-07-05 | 2004-01-20 | Марвел Лайфсайнсез Прайвит Лимитед | Способ получения бензолсульфоната амлодипина |
| KR100538641B1 (ko) * | 2002-07-30 | 2005-12-22 | 씨제이 주식회사 | 암로디핀의 유기산염 |
| KR100496436B1 (ko) | 2002-07-30 | 2005-06-20 | 씨제이 주식회사 | 암로디핀의 유기산염 |
| KR100462304B1 (ko) * | 2002-07-30 | 2004-12-17 | 씨제이 주식회사 | 암로디핀의 유기산염 |
| KR20040011751A (ko) * | 2002-07-30 | 2004-02-11 | 씨제이 주식회사 | 암로디핀의 유기산염 |
| KR100467669B1 (ko) | 2002-08-21 | 2005-01-24 | 씨제이 주식회사 | 암로디핀의 유기산염 |
| EA007613B1 (ru) | 2002-08-29 | 2006-12-29 | Тайсо Фармасьютикал Ко., Лтд. | Бензолсульфонатная соль (2s,4s)-1-циано-4-фтор-1-[(2-гидрокси-1,1-диметил)этиламино]ацетилпирролидина |
| US6784297B2 (en) * | 2002-09-04 | 2004-08-31 | Kopran Limited | Process for the preparation of anti-ischemic and anti-hypertensive drug amlodipine besylate |
| AU2003260984A1 (en) * | 2002-09-11 | 2004-04-30 | Hanlim Pharmaceutical Co., Ltd. | S-(-)-amlodipine nicotinate and process for the preparation thereof |
| AU2003253460A1 (en) * | 2002-09-19 | 2004-04-08 | Cj Corporation | Crystalline organic acid salt of amlodipine |
| US7166641B2 (en) * | 2002-10-02 | 2007-01-23 | Yung Shin Pharmaceutical Industrial Co., Ltd. | Pharmaceutically acceptable salts containing local anesthetic and anti-inflammatory activities and methods for preparing the same |
| EP1407773A1 (en) * | 2002-10-08 | 2004-04-14 | Council of Scientific and Industrial Research | A process for the preparation of s (-) amlodipine salts |
| US20040072879A1 (en) * | 2002-10-10 | 2004-04-15 | Dr. Reddy's Laboratories Limited | Crystalline 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine maleate salt (Amlodipine) |
| AU2002368531A1 (en) * | 2002-12-30 | 2004-07-22 | Eos Eczacibasi Ozgun Kimyasal Urunler Sanayi Ve Ticaret A.S. | Isolation of dihydropyridine derivative and preparation salts thereof |
| ES2500292T3 (es) | 2003-01-27 | 2014-09-30 | Hanmi Science Co., Ltd. | Camsilato de amlodipina amorfo, estable, procedimiento para la reparación del mismo y composición para su administración oral |
| BRPI0406987A (pt) * | 2003-01-31 | 2006-01-10 | Sankyo Co | Medicamento para a prevenção e/ou tratamento de arteriosclerose, medicamentos para a inibição de proliferação de células do músculo liso vascular, de formação de neoìntima dos vasos sanguìneos e de remodelação vascular, medicamento para a prevenção de restenose que segue intervenção coronária percutânea, e, medicamentos para a profilaxia e/ou tratamento de hipertensão ou doenças causadas por hipertensão ou doenças causadas por hipertensão, de doenças cardìacas, de angina do peito, de infarto miocárdico, de arritmia, de morte súbita, de insuficiência cardìaca, de hipertrofia cardìaca, de doenças renais, de nefropatia diabética, de glomerulonefrite, de nefrosclerose, de doenças cerebrovasculares, de infarto cerebral, e de hemorragia cerebral |
| KR20040072363A (ko) * | 2003-02-12 | 2004-08-18 | 주식회사 대웅 | 신규한 암로디핀 사이클라메이트 염 및 그의 제조방법 |
| US20060270715A1 (en) * | 2003-02-28 | 2006-11-30 | Singh Romi B | Dosage forms of amlodipine and processes for their preparation |
| KR20060013376A (ko) | 2003-04-25 | 2006-02-09 | 카딜라 헬스케어 리미티드 | 클로피도그렐 염과 그 제조 방법 |
| DE112004000712T5 (de) * | 2003-04-25 | 2006-10-19 | Cipla Ltd. | Verfahren zur Herstellung von Amlodipinmesilat-Monohydrat |
| US20050182125A1 (en) * | 2003-05-16 | 2005-08-18 | Ambit Biosciences Corporation | Pyrrole compounds and uses thereof |
| AU2004247627A1 (en) * | 2003-05-16 | 2004-12-23 | Ambit Biosciences Corporation | Pyrrole compounds and uses thereof |
| US7923467B2 (en) | 2003-05-30 | 2011-04-12 | Ranbaxy Laboratories, Inc. | Substituted pyrrole derivatives and their use as HMG-CO inhibitors |
| RU2239433C1 (ru) * | 2003-06-09 | 2004-11-10 | Закрытое акционерное общество "Фармацевтическое предприятие "Оболенское" | Лекарственная форма, обладающая вазодилатирующим, антиангинальным, гипотензивным и спазмолитическим действием, и способ ее изготовления |
| US7145125B2 (en) | 2003-06-23 | 2006-12-05 | Advanced Optical Technologies, Llc | Integrating chamber cone light using LED sources |
| US20050048118A1 (en) * | 2003-07-25 | 2005-03-03 | Joan Cucala Escoi | Modified release venlafaxine hydrochloride tablets |
| WO2005042485A1 (en) * | 2003-10-30 | 2005-05-12 | Sk Chemicals, Co., Ltd. | Acid added salts of amlodipine |
| KR100841409B1 (ko) * | 2003-12-16 | 2008-06-25 | 에스케이케미칼주식회사 | 암로디핀 겐티세이트 염과 이의 제조방법 |
| US7262318B2 (en) * | 2004-03-10 | 2007-08-28 | Pfizer, Inc. | Substituted heteroaryl- and phenylsulfamoyl compounds |
| WO2005089353A2 (en) * | 2004-03-16 | 2005-09-29 | Sepracor Inc. | (s)-amlodipine malate |
| JP4880591B2 (ja) | 2004-06-04 | 2012-02-22 | テバ ファーマシューティカル インダストリーズ リミティド | イルベサルタンを含む医薬組成物 |
| US20050288340A1 (en) * | 2004-06-29 | 2005-12-29 | Pfizer Inc | Substituted heteroaryl- and phenylsulfamoyl compounds |
| DE602005019582D1 (de) * | 2004-08-30 | 2010-04-08 | Seo Hong Yoo | Nervenschutzwirkung von aufgelöster udca bei einem fokalen ischämischen modell |
| KR20070084211A (ko) * | 2004-10-15 | 2007-08-24 | 유서홍 | 약제학적 화합물의 독성을 감소시키기 위한 방법 및 조성물 |
| US20060142241A1 (en) * | 2004-11-01 | 2006-06-29 | Yoo Seo H | Methods and compositions for reducing neurodegeneration in amyotrophic lateral sclerosis |
| AU2005308575A1 (en) * | 2004-11-23 | 2006-06-01 | Warner-Lambert Company Llc | 7-(2h-pyrazol-3-yl)-3, 5-dihyroxy-heptanoic acid derivatives as HMG Co-A reductase inhibitors for the treatment of lipidemia |
| WO2006059217A1 (en) * | 2004-12-01 | 2006-06-08 | Ranbaxy Laboratories Limited | Stable solid dosage forms of amlodipine besylate and processes for their preparation |
| US20080305158A1 (en) * | 2004-12-28 | 2008-12-11 | Ranbaxy Laboratories Limited | Methods For the Preparation of Stable Pharmaceutical Solid Dosage Forms of Atorvastatin and Amlodipine |
| WO2006085208A2 (en) * | 2005-02-11 | 2006-08-17 | Ranbaxy Laboratories Limited | Stable solid dosage forms of amlodipine and benazepril |
| CA2610838A1 (en) * | 2005-06-07 | 2006-12-14 | Ramot At Tel Aviv University Ltd. | Novel salts of conjugated psychotropic drugs and processes of preparing same |
| BRPI0612674B8 (pt) * | 2005-06-27 | 2021-05-25 | Daiichi Sankyo Co Ltd | preparação farmacêutica, uso de um antagonista do receptor de angiotensina ii e um bloqueador do canal de cálcio |
| DE602005005706T2 (de) * | 2005-09-28 | 2009-04-16 | Teva Pharmaceutical Industries Ltd. | Stabile Arzneimittelkombinationen von Amlodipinbesylat und Benazeprilhydrochlorid |
| US8158146B2 (en) | 2005-09-28 | 2012-04-17 | Teva Pharmaceutical Industries Ltd. | Stable combinations of amlodipine besylate and benazepril hydrochloride |
| US7741317B2 (en) | 2005-10-21 | 2010-06-22 | Bristol-Myers Squibb Company | LXR modulators |
| US8026377B2 (en) | 2005-11-08 | 2011-09-27 | Ranbaxy Laboratories, Limited | Process for (3R, 5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-[(4-hydroxy methyl phenyl amino) carbonyl]-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid hemi calcium salt |
| US7888376B2 (en) | 2005-11-23 | 2011-02-15 | Bristol-Myers Squibb Company | Heterocyclic CETP inhibitors |
| FR2894826B1 (fr) * | 2005-12-21 | 2010-10-22 | Servier Lab | Nouvelle association d'un inhibiteur du courant if sinusal et d'un inhibiteur calcique et les compositions pharmaceutiques qui la contiennent |
| WO2008010223A2 (en) | 2006-07-17 | 2008-01-24 | Ramot At Tel Aviv University Ltd. | Conjugates comprising a psychotropic drug or a gaba agonist and an organic acid and their use in treating pain and other cns disorders |
| KR100795313B1 (ko) | 2006-09-05 | 2008-01-21 | 현대약품 주식회사 | 암로디핀 베실레이트를 포함하는 약학 조성물 |
| TWI399223B (zh) * | 2006-09-15 | 2013-06-21 | Daiichi Sankyo Co Ltd | 奧美沙坦酯及氨氯地平之固體劑型 |
| US20080096863A1 (en) * | 2006-10-19 | 2008-04-24 | Torrent Pharmaceuticals Limited | Stable pharmaceutical compositions of calcium channel blocker and an ACE inhibitor |
| CN101167724B (zh) * | 2006-10-25 | 2012-08-22 | 北京华安佛医药研究中心有限公司 | 含有氨氯地平的药物组合物在制备治疗下尿路疾病药物中的用途 |
| WO2008070496A2 (en) | 2006-12-01 | 2008-06-12 | Bristol-Myers Squibb Company | N- ( (3-benzyl) -2, 2- (bis-phenyl) -propan-1-amine derivatives as cetp inhibitors for the treatment of atherosclerosis and cardiovascular diseases |
| EP2125702A1 (en) * | 2006-12-21 | 2009-12-02 | Xenoport, Inc. | Levodopa dimethyl-substituted diester prodrugs, compositions, and methods of use |
| CN101652131A (zh) | 2007-01-29 | 2010-02-17 | 韩兀制药株式会社 | N,n-二甲基亚氨基二碳亚氨酸二酰胺乙酸盐、其制备方法和包含其的药物组合物 |
| US20080249141A1 (en) * | 2007-04-06 | 2008-10-09 | Palepu Nageswara R | Co-therapy with and combinations of statins and 1,4-dihydropyridine-3,5-dicarboxydiesters |
| US8748648B2 (en) | 2007-09-06 | 2014-06-10 | Nektar Therapeutics | Oligomer-calcium channel blocker conjugates |
| US8143314B1 (en) * | 2007-09-13 | 2012-03-27 | Robert Carl Stover | Methods and formulations for treating ineffective or decreased esophageal motility |
| EP2203418B1 (en) * | 2007-09-21 | 2017-10-25 | HanAll Biopharma Co., Ltd. | N,n-dimethyl imidodicarbonimidic diamide dicarboxylate, method for producing the same and pharmaceutical compositions comprising the same |
| WO2009084003A1 (en) | 2007-12-31 | 2009-07-09 | Lupin Limited | Pharmaceutical compositions of amlodipine and valsartan |
| US8207369B2 (en) | 2008-02-11 | 2012-06-26 | Ramot At Tel-Aviv University Ltd. | Conjugates for treating neurodegenerative diseases and disorders |
| RU2359672C1 (ru) * | 2008-02-18 | 2009-06-27 | Зао "Биоком" | Твердая лекарственная форма, предназначенная для лечения артериальной гипертензии и стенокардии, и способ ее получения |
| CN101564536B (zh) * | 2008-04-21 | 2010-12-15 | 鲁南制药集团股份有限公司 | 一种治疗高血压的药物组合物缓控释制剂 |
| US8338439B2 (en) | 2008-06-27 | 2012-12-25 | Celgene Avilomics Research, Inc. | 2,4-disubstituted pyrimidines useful as kinase inhibitors |
| US11351168B1 (en) | 2008-06-27 | 2022-06-07 | Celgene Car Llc | 2,4-disubstituted pyrimidines useful as kinase inhibitors |
| NZ603525A (en) | 2008-06-27 | 2015-02-27 | Celgene Avilomics Res Inc | Pyrimidine based compound and uses thereof |
| EP2349973A2 (en) * | 2008-10-20 | 2011-08-03 | XenoPort, Inc. | Methods of synthesizing a levodopa ester prodrug |
| US8399513B2 (en) | 2008-10-20 | 2013-03-19 | Xenoport, Inc. | Levodopa prodrug mesylate hydrate |
| WO2010070705A1 (ja) * | 2008-12-17 | 2010-06-24 | 株式会社メドレックス | アムロジピンの安定な含水経口製剤 |
| MA33056B1 (fr) | 2009-01-23 | 2012-02-01 | Hanmi Holding Co Ltd | Composition pharmaceutique solide comprenant de l'amlodipine et du losartan et son procede de fabrication |
| NZ601747A (en) * | 2009-11-09 | 2014-08-29 | Xenoport Inc | Pharmaceutical compositions and oral dosage forms of a levodopa prodrug and methods of use |
| US8975251B2 (en) | 2009-12-09 | 2015-03-10 | Bar-Ilan University | Methods of improving cognitive functions |
| PT2534153T (pt) | 2010-02-12 | 2016-12-27 | Pfizer | Sais e polimorfos de 8-fluoro-2-{4-[(metilamino}metil]fenil}-1,3,4,5-tetrahidro-6h-azepino[5,4,3-cd]indol-6-ona |
| JP2013520488A (ja) | 2010-02-24 | 2013-06-06 | ラモット・アット・テル・アビブ・ユニバーシテイ・リミテッド | ペルフェナジン−ｇａｂａのトリメシラート塩の結晶性形態物及びその製法方法 |
| WO2011117876A1 (en) | 2010-03-26 | 2011-09-29 | Fdc Limited | An improved process for the preparation of amlodipine free base and acid addition salts thereof |
| IT1400309B1 (it) | 2010-05-10 | 2013-05-24 | Menarini Int Operations Lu Sa | Associazione di inibitori della xantina ossidasi e calcio antagonisti e loro uso. |
| EP2425859A1 (en) | 2010-08-08 | 2012-03-07 | Abdi Ibrahim Ilac Sanayi ve Ticaret Anonim Sirketi | Olmesartan formulations |
| AU2011289604C1 (en) * | 2010-08-10 | 2016-04-21 | Celgene Avilomics Research, Inc. | Besylate salt of a BTK inhibitor |
| WO2012038963A1 (en) | 2010-09-22 | 2012-03-29 | Ramot At Tel-Aviv University Ltd. | An acid addition salt of a nortriptyline-gaba conjugate and a process of preparing same |
| CA2815858C (en) | 2010-11-01 | 2018-10-16 | Celgene Avilomics Research, Inc. | Heterocyclic compounds and uses thereof |
| JP5956999B2 (ja) | 2010-11-01 | 2016-07-27 | セルジーン アヴィロミクス リサーチ， インコーポレイテッド | ヘテロアリール化合物およびその使用 |
| JP5957003B2 (ja) | 2010-11-10 | 2016-07-27 | セルジーン アヴィロミクス リサーチ， インコーポレイテッド | 変異体選択的ｅｇｆｒ阻害剤およびその使用 |
| WO2012071524A1 (en) * | 2010-11-24 | 2012-05-31 | Ratiopharm Gmbh | Arylsulfonate salts of fingolimod and processes for preparation thereof |
| WO2013063401A1 (en) | 2011-10-28 | 2013-05-02 | Celgene Avilomics Research, Inc. | Methods of treating a bruton's tyrosine kinase disease or disorder |
| MX356753B (es) | 2012-03-15 | 2018-06-12 | Celgene Avilomics Res Inc | Formas solidas de un inhibidor de cinasa del receptor del factor de crecimiento epidermico. |
| HRP20181784T1 (hr) | 2012-03-15 | 2018-12-28 | Celgene Car Llc | Soli epidermalnog faktora rasta inhibitora receptora kinaze |
| PL236001B1 (pl) | 2012-12-21 | 2020-11-30 | Adamed Spolka Z Ograniczona Odpowiedzialnoscia | Złożona kompozycja farmaceutyczna zawierająca kandesartan cyleksetylu oraz amlodypinę, sposób jej wytwarzania oraz jednostkowa postać dawkowania zawierająca tę kompozycję |
| WO2014100748A1 (en) | 2012-12-21 | 2014-06-26 | Celgene Avilomics Research, Inc. | Heteroaryl compounds and uses thereof |
| US9561228B2 (en) | 2013-02-08 | 2017-02-07 | Celgene Avilomics Research, Inc. | ERK inhibitors and uses thereof |
| US20150374713A1 (en) | 2013-02-08 | 2015-12-31 | Wockhardt Limited | Stable pharmeceutical composition of amlodipine and benazepril or salts thereof |
| AU2014255381A1 (en) | 2013-04-17 | 2015-10-08 | Pfizer Inc. | N-piperidin-3-ylbenzamide derivatives for treating cardiovascular diseases |
| US9492471B2 (en) | 2013-08-27 | 2016-11-15 | Celgene Avilomics Research, Inc. | Methods of treating a disease or disorder associated with Bruton'S Tyrosine Kinase |
| US9415049B2 (en) | 2013-12-20 | 2016-08-16 | Celgene Avilomics Research, Inc. | Heteroaryl compounds and uses thereof |
| TW201613892A (en) | 2014-08-13 | 2016-04-16 | Celgene Avilomics Res Inc | Forms and compositions of an ERK inhibitor |
| WO2016055901A1 (en) | 2014-10-08 | 2016-04-14 | Pfizer Inc. | Substituted amide compounds |
| CN104610130A (zh) * | 2015-01-22 | 2015-05-13 | 华东理工常熟研究院有限公司 | 氨氯地平-棕榈酸离子液体及其制备方法和用途 |
| CN104529877A (zh) * | 2015-01-22 | 2015-04-22 | 华东理工常熟研究院有限公司 | 氨氯地平-癸酸离子液体及其制备方法和用途 |
| CN104523588A (zh) * | 2015-01-22 | 2015-04-22 | 华东理工常熟研究院有限公司 | 氨氯地平-硬脂酸离子液体及其制备方法和用途 |
| WO2017030893A1 (en) | 2015-08-14 | 2017-02-23 | Endocyte, Inc. | Method of imaging with a chelating compound |
| US20180303811A1 (en) | 2015-10-23 | 2018-10-25 | Ftf Pharma Private Limited | Oral solution of dihydropyridine derivatives |
| CN105395495A (zh) * | 2015-11-30 | 2016-03-16 | 宜昌东阳光长江药业股份有限公司 | 一种含有苯磺酸氨氯地平的组合物及其制备方法 |
| EP3219309A1 (en) | 2016-03-17 | 2017-09-20 | K.H.S. Pharma Holding GmbH | Fixed dosed pharmaceutical composition comprising amlodipine, candesartan cilexetil and hydrochlorothiazide for the treatment of hypertension |
| EP3463309B1 (en) | 2016-05-30 | 2020-06-17 | Boehringer Ingelheim International GmbH | Fixed dose combination of telmisartan, hydrochlorothiazide and amlodipine |
| WO2018067959A1 (en) | 2016-10-07 | 2018-04-12 | Silvergate Pharmaceuticals, Inc. | Amlodipine formulations |
| US10350171B2 (en) | 2017-07-06 | 2019-07-16 | Dexcel Ltd. | Celecoxib and amlodipine formulation and method of making the same |
| EP3501502A1 (en) | 2017-12-20 | 2019-06-26 | Midas Pharma GmbH | Fixed dosed pharmaceutical compositions comprising amlodipine, ramipril and atorvastatin |
| EP3773574A4 (en) | 2018-04-11 | 2022-03-02 | Silvergate Pharmaceuticals, Inc. | AMLODIPINE FORMULATIONS |
| AU2019285170A1 (en) | 2018-06-14 | 2021-01-28 | Astrazeneca Uk Limited | Methods for lowering blood pressure with a dihydropyridine-type calcium channel blocker pharmaceutical composition |
| CN113574055B (zh) | 2019-01-18 | 2024-07-23 | 阿斯利康(瑞典)有限公司 | Pcsk9抑制剂及其使用方法 |
| US11253474B1 (en) | 2021-02-01 | 2022-02-22 | Liqmeds Worldwide Limited | Pharmaceutical solution of amlodipine |
| EP4052695A1 (en) | 2021-03-05 | 2022-09-07 | Midas Pharma GmbH | Stable oral fixed-dose immediate release pharmaceutical compositions comprising amlodipine, atorvastatin and candesartan cilexetil |
| WO2023285646A1 (en) | 2021-07-15 | 2023-01-19 | Adamed Pharma S.A | A pharmaceutical composition comprising amlodipine, candesartan cilexetil and hydrochlorothiazide for the treatment of hypertension |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CS228917B2 (en) * | 1981-03-14 | 1984-05-14 | Pfizer | Method of preparing substituted derivatives of 1,4-dihydropyridine |
| DK161312C (da) * | 1982-03-11 | 1991-12-09 | Pfizer | Analogifremgangsmaade til fremstilling af 2-aminoalkoxymethyl-4-phenyl-6-methyl-1,4-dihydropyridin-3,5-dicarboxylsyreestere eller syreadditionssalte deraf samt phthalimidoderivater til anvendelse som udgangsmateriale ved fremgangsmaaden |
| ZA839187B (en) * | 1982-12-10 | 1984-07-25 | Ciba Geigy Ag | Amide compounds |
-
1986
- 1986-04-04 GB GB868608335A patent/GB8608335D0/en active Pending
-
1987
- 1987-03-18 LU LU86812A patent/LU86812A1/fr unknown
- 1987-03-30 DE DE19873710457 patent/DE3710457A1/de not_active Withdrawn
- 1987-03-30 CN CN87102493A patent/CN1023800C/zh 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 ES ES87302767T patent/ES2012803B3/es not_active Expired - Lifetime
- 1987-03-31 SE SE8701348A patent/SE463457B/sv not_active IP Right Cessation
- 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
- 1987-04-01 MY MYPI87000413A patent/MY101177A/en unknown
- 1987-04-01 MX MX584787A patent/MX5847A/es unknown
- 1987-04-02 IN IN281/DEL/87A patent/IN168414B/en unknown
- 1987-04-02 CA CA000533732A patent/CA1321393C/en not_active Expired - Lifetime
- 1987-04-02 GR GR870525A patent/GR870525B/el unknown
- 1987-04-02 CS CS872363A patent/CS265237B2/cs not_active IP Right Cessation
- 1987-04-02 PH PH35098A patent/PH24348A/en unknown
- 1987-04-02 AP APAP/P/1987/000060A patent/AP50A/en active
- 1987-04-02 AR AR87307197A patent/AR242562A1/es active
- 1987-04-02 YU YU580/87A patent/YU44801B/xx unknown
- 1987-04-02 PT PT84611A patent/PT84611B/pt unknown
- 1987-04-03 DK DK170187A patent/DK171708B1/da active IP Right Grant
- 1987-04-03 IE IE86987A patent/IE59457B1/en not_active IP Right Cessation
- 1987-04-03 BE BE8700349A patent/BE1000130A4/fr not_active IP Right Cessation
- 1987-04-03 IL IL82101A patent/IL82101A/xx not_active IP Right Cessation
- 1987-04-03 DD DD87301485A patent/DD265142A5/de unknown
- 1987-04-03 UA UA4202353A patent/UA6344A1/uk unknown
- 1987-04-03 ES ES8700965A patent/ES2002599A6/es not_active Expired
- 1987-04-03 SU SU874202353A patent/SU1498388A3/ru active
- 1987-04-03 NL NL8700791A patent/NL8700791A/nl not_active Application Discontinuation
- 1987-04-03 NO NO871408A patent/NO172181C/no unknown
- 1987-04-03 ZA ZA872439A patent/ZA872439B/xx unknown
- 1987-04-03 JP JP62082787A patent/JPS62240660A/ja active Granted
- 1987-04-03 HU HU871450A patent/HU196962B/hu unknown
- 1987-04-03 PL PL1987264982A patent/PL149532B1/pl unknown
- 1987-04-03 MA MA21175A patent/MA20938A1/fr unknown
- 1987-04-03 NZ NZ219868A patent/NZ219868A/xx unknown
- 1987-04-03 FR FR8704705A patent/FR2596758B1/fr not_active Expired
- 1987-04-03 FI FI871470A patent/FI85017C/fi not_active IP Right Cessation
- 1987-04-03 IT IT19977/87A patent/IT1203853B/it active
- 1987-04-04 KR KR1019870003209A patent/KR950006710B1/ko not_active Expired - Lifetime
-
1988
- 1988-10-13 US US07/256,938 patent/US4879303A/en not_active Expired - Lifetime
-
1990
- 1990-03-21 GR GR90400158T patent/GR3000394T3/el unknown
-
1991
- 1991-11-22 CZ CS19913539A patent/CZ289095B6/cs not_active IP Right Cessation
- 1991-11-22 SK SK3539-91A patent/SK278435B6/sk unknown
-
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
-
1993
- 1993-05-14 CY CY1669A patent/CY1669A/xx unknown
-
1994
- 1994-07-26 EC EC1994001129A patent/ECSP941129A/es unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CS265237B2 (en) | Process for preparing salt of 3-ethyl-5-methyl-2-/aminoethoxymethyl/4-/2-chlorphenyl/-1,4-dihydro-6-methylpyridin-3,5-dicarboxylate with benzensulphonic acid | |
| US7579475B2 (en) | S-(-)-amlodipine nicotinate and process for the preparation thereof | |
| CZ20032583A3 (cs) | Nový amlodipinkamsylát a způsob jeho přípravy | |
| US20070135488A1 (en) | Amlodipine nicotinate and process for the preparation thereof | |
| KR100538641B1 (ko) | 암로디핀의 유기산염 | |
| KR950007228B1 (ko) | 암로디핀의 베실레이트염 | |
| SI8710580A8 (sl) | Postopek za pridobivanje benzolsulfonatne soli 3-etil-5-metil-2-(2-aminoetoksimetil)- 4-{2-klorofenil)-1.4-dihidro-6- metilpiridin-3.5-dikarboksilata | |
| US6756390B2 (en) | Organic acid salt of amlodipine | |
| MXPA05001241A (es) | Sal acida organica de amilodipina. | |
| KR100765464B1 (ko) | 암로디핀 말레이트를 포함하는 약제조성물 및 그 제조 방법 | |
| US20040030143A1 (en) | Organic acid salt of amlodipine |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| IF00 | In force as of 2000-06-30 in czech republic | ||
| MK4A | Patent expired |
Effective date: 20020402 |