NZ521292A - Sustained release ranolazine formulations - Google Patents
Sustained release ranolazine formulationsInfo
- Publication number
- NZ521292A NZ521292A NZ521292A NZ52129201A NZ521292A NZ 521292 A NZ521292 A NZ 521292A NZ 521292 A NZ521292 A NZ 521292A NZ 52129201 A NZ52129201 A NZ 52129201A NZ 521292 A NZ521292 A NZ 521292A
- Authority
- NZ
- New Zealand
- Prior art keywords
- ranolazine
- dosage form
- pharmaceutical dosage
- plasma
- hours
- Prior art date
Links
- XKLMZUWKNUAPSZ-UHFFFAOYSA-N N-(2,6-dimethylphenyl)-2-{4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl}acetamide Chemical compound COC1=CC=CC=C1OCC(O)CN1CCN(CC(=O)NC=2C(=CC=CC=2C)C)CC1 XKLMZUWKNUAPSZ-UHFFFAOYSA-N 0.000 title claims abstract description 257
- 229960000213 ranolazine Drugs 0.000 title claims abstract description 254
- 238000013268 sustained release Methods 0.000 title claims abstract description 84
- 239000012730 sustained-release form Substances 0.000 title claims abstract description 84
- 239000000203 mixture Substances 0.000 title description 104
- 238000009472 formulation Methods 0.000 title description 91
- 230000036470 plasma concentration Effects 0.000 claims abstract description 48
- 239000002552 dosage form Substances 0.000 claims abstract description 39
- 206010002383 Angina Pectoris Diseases 0.000 claims abstract description 31
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 9
- 208000010125 myocardial infarction Diseases 0.000 claims abstract description 9
- 201000001068 Prinzmetal angina Diseases 0.000 claims abstract description 8
- 206010003119 arrhythmia Diseases 0.000 claims abstract description 8
- 230000006793 arrhythmia Effects 0.000 claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 31
- 238000011282 treatment Methods 0.000 claims description 25
- 238000002360 preparation method Methods 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 229940068196 placebo Drugs 0.000 description 37
- 239000000902 placebo Substances 0.000 description 37
- 239000011230 binding agent Substances 0.000 description 29
- 239000003826 tablet Substances 0.000 description 25
- 101100094849 Homo sapiens SLC22A4 gene Proteins 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 23
- 102100036928 Solute carrier family 22 member 4 Human genes 0.000 description 23
- 238000011987 exercise tolerance test Methods 0.000 description 23
- 239000012458 free base Substances 0.000 description 22
- 239000002585 base Substances 0.000 description 21
- 230000001419 dependent effect Effects 0.000 description 20
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
- 238000004090 dissolution Methods 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- 230000003257 anti-anginal effect Effects 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- 229940079593 drug Drugs 0.000 description 11
- 239000003814 drug Substances 0.000 description 11
- 239000008187 granular material Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- 208000007718 Stable Angina Diseases 0.000 description 9
- 239000004004 anti-anginal agent Substances 0.000 description 9
- 229920001577 copolymer Polymers 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 230000002253 anti-ischaemic effect Effects 0.000 description 8
- 239000002876 beta blocker Substances 0.000 description 8
- 229940097320 beta blocking agent Drugs 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 239000012729 immediate-release (IR) formulation Substances 0.000 description 8
- 230000001965 increasing effect Effects 0.000 description 8
- 235000019359 magnesium stearate Nutrition 0.000 description 8
- 229920003145 methacrylic acid copolymer Polymers 0.000 description 8
- 210000002784 stomach Anatomy 0.000 description 8
- 230000036772 blood pressure Effects 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- RJNSNFZXAZXOFX-UHFFFAOYSA-N n-(2,6-dimethylphenyl)-2-[4-[2-hydroxy-3-(2-methoxyphenoxy)propyl]piperazin-1-yl]acetamide;hydron;dichloride Chemical class Cl.Cl.COC1=CC=CC=C1OCC(O)CN1CCN(CC(=O)NC=2C(=CC=CC=2C)C)CC1 RJNSNFZXAZXOFX-UHFFFAOYSA-N 0.000 description 7
- 239000000546 pharmaceutical excipient Substances 0.000 description 7
- 230000002035 prolonged effect Effects 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- 238000002560 therapeutic procedure Methods 0.000 description 7
- 241000282412 Homo Species 0.000 description 6
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 6
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 6
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 6
- 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 6
- 229940016286 microcrystalline cellulose Drugs 0.000 description 6
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 6
- 239000008108 microcrystalline cellulose Substances 0.000 description 6
- 229940127291 Calcium channel antagonist Drugs 0.000 description 5
- 229920003135 Eudragit® L 100-55 Polymers 0.000 description 5
- 238000000540 analysis of variance Methods 0.000 description 5
- 239000012530 fluid Substances 0.000 description 5
- 208000028867 ischemia Diseases 0.000 description 5
- 230000036961 partial effect Effects 0.000 description 5
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 5
- 238000009097 single-agent therapy Methods 0.000 description 5
- -1 2-methoxyphenoxy Chemical group 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- 239000008280 blood Substances 0.000 description 4
- 210000004369 blood Anatomy 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- 229940117841 methacrylic acid copolymer Drugs 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 150000002823 nitrates Chemical class 0.000 description 4
- 239000006186 oral dosage form Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 4
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 4
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- 229920002785 Croscarmellose sodium Polymers 0.000 description 3
- 102100028701 General vesicular transport factor p115 Human genes 0.000 description 3
- 101000767151 Homo sapiens General vesicular transport factor p115 Proteins 0.000 description 3
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 229940124345 antianginal agent Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000000747 cardiac effect Effects 0.000 description 3
- 239000003086 colorant Substances 0.000 description 3
- 239000007891 compressed tablet Substances 0.000 description 3
- 229960001681 croscarmellose sodium Drugs 0.000 description 3
- 235000010947 crosslinked sodium carboxy methyl cellulose Nutrition 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 3
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002483 medication Methods 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 229940124531 pharmaceutical excipient Drugs 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- 229920003163 Eudragit® NE 30 D Polymers 0.000 description 2
- 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- LCTONWCANYUPML-UHFFFAOYSA-M Pyruvate Chemical compound CC(=O)C([O-])=O LCTONWCANYUPML-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 238000000692 Student's t-test Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 229920013820 alkyl cellulose Polymers 0.000 description 2
- 230000001174 ascending effect Effects 0.000 description 2
- 210000005013 brain tissue Anatomy 0.000 description 2
- 235000010980 cellulose Nutrition 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000001913 cellulose Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000013270 controlled release Methods 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 238000009505 enteric coating Methods 0.000 description 2
- 239000002702 enteric coating Substances 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000007888 film coating Substances 0.000 description 2
- 238000009501 film coating Methods 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 230000000004 hemodynamic effect Effects 0.000 description 2
- 229920013821 hydroxy alkyl cellulose Polymers 0.000 description 2
- 230000001146 hypoxic effect Effects 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- 235000010981 methylcellulose Nutrition 0.000 description 2
- 210000004165 myocardium Anatomy 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 2
- 150000003021 phthalic acid derivatives Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 210000002027 skeletal muscle Anatomy 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012353 t test Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- XKLMZUWKNUAPSZ-FQEVSTJZSA-N (S)-ranolazine Chemical compound COC1=CC=CC=C1OC[C@@H](O)CN1CCN(CC(=O)NC=2C(=CC=CC=2C)C)CC1 XKLMZUWKNUAPSZ-FQEVSTJZSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- 230000002407 ATP formation Effects 0.000 description 1
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-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
- 206010002388 Angina unstable Diseases 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 208000002330 Congenital Heart Defects Diseases 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
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 description 1
- 229920003164 Eudragit® NE 40 D Polymers 0.000 description 1
- 229920003153 Eudragit® NE polymer Polymers 0.000 description 1
- 229920003134 Eudragit® polymer Polymers 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 206010022562 Intermittent claudication Diseases 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 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
- 208000007177 Left Ventricular Hypertrophy Diseases 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001274656 Marisa Species 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical group CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229920003091 Methocel™ Polymers 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 208000005764 Peripheral Arterial Disease Diseases 0.000 description 1
- 206010063837 Reperfusion injury Diseases 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 208000007814 Unstable Angina Diseases 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 235000021152 breakfast Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 1
- 229920003086 cellulose ether Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 208000028831 congenital heart disease Diseases 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 description 1
- 229960005156 digoxin Drugs 0.000 description 1
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000034659 glycolysis Effects 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 208000018578 heart valve disease Diseases 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 201000004332 intermediate coronary syndrome Diseases 0.000 description 1
- 208000021156 intermittent vascular claudication Diseases 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000011872 intimate mixture Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000007449 liver function test Methods 0.000 description 1
- 210000003750 lower gastrointestinal tract Anatomy 0.000 description 1
- 238000007726 management method Methods 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 229940063557 methacrylate Drugs 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- 239000011812 mixed powder Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 208000031225 myocardial ischemia Diseases 0.000 description 1
- 230000002746 orthostatic effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940100467 polyvinyl acetate phthalate Drugs 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000010410 reperfusion Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000013526 supercooled liquid Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000007939 sustained release tablet Substances 0.000 description 1
- 230000009747 swallowing Effects 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 210000002438 upper gastrointestinal tract Anatomy 0.000 description 1
- 238000002562 urinalysis Methods 0.000 description 1
- 229920006163 vinyl copolymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- 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
- A61K9/2027—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
-
- 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
- A61K9/28—Dragees; Coated pills or tablets, e.g. with film or compression coating
- A61K9/2806—Coating materials
- A61K9/2833—Organic macromolecular compounds
- A61K9/284—Organic macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone
- A61K9/2846—Poly(meth)acrylates
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/520,932 US6479496B1 (en) | 1998-09-10 | 2000-03-08 | Methods for treating angina with ranolazine |
| PCT/US2001/007287 WO2001066093A2 (en) | 2000-03-08 | 2001-03-07 | Sustained release ranolazine formulations |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ521292A true NZ521292A (en) | 2008-07-31 |
Family
ID=24074628
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ521292A NZ521292A (en) | 2000-03-08 | 2001-03-07 | Sustained release ranolazine formulations |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US6479496B1 (enExample) |
| EP (1) | EP1263439A2 (enExample) |
| JP (2) | JP4108980B2 (enExample) |
| CN (1) | CN1323664C (enExample) |
| AU (3) | AU2001240092B8 (enExample) |
| BR (1) | BR0109091A (enExample) |
| CA (1) | CA2402222C (enExample) |
| CZ (1) | CZ20022996A3 (enExample) |
| HU (1) | HUP0204409A3 (enExample) |
| IL (1) | IL151575A0 (enExample) |
| MX (1) | MXPA02008654A (enExample) |
| NO (1) | NO20024270L (enExample) |
| NZ (1) | NZ521292A (enExample) |
| PL (1) | PL357273A1 (enExample) |
| RU (1) | RU2002126615A (enExample) |
| WO (1) | WO2001066093A2 (enExample) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6303607B1 (en) * | 1998-09-10 | 2001-10-16 | Cv Therapeutics, Inc. | Method for administering a sustained release ranolanolazine formulation |
| US6479496B1 (en) * | 1998-09-10 | 2002-11-12 | Cv Therapeutics, Inc. | Methods for treating angina with ranolazine |
| US6544555B2 (en) | 2000-02-24 | 2003-04-08 | Advancis Pharmaceutical Corp. | Antibiotic product, use and formulation thereof |
| US6565882B2 (en) | 2000-02-24 | 2003-05-20 | Advancis Pharmaceutical Corp | Antibiotic composition with inhibitor |
| US20020068078A1 (en) | 2000-10-13 | 2002-06-06 | Rudnic Edward M. | Antifungal product, use and formulation thereof |
| US6541014B2 (en) | 2000-10-13 | 2003-04-01 | Advancis Pharmaceutical Corp. | Antiviral product, use and formulation thereof |
| AU2003248558B8 (en) | 2002-05-21 | 2009-07-09 | Gilead Sciences, Inc. | Method of treating diabetes |
| US8822473B2 (en) * | 2002-05-21 | 2014-09-02 | Gilead Sciences, Inc. | Method of treating diabetes |
| JP2006528190A (ja) | 2003-07-21 | 2006-12-14 | アドバンシス ファーマスーティカル コーポレイション | 抗生物質製剤、その使用法及び作成方法 |
| CA2533178C (en) | 2003-07-21 | 2014-03-11 | Advancis Pharmaceutical Corporation | Antibiotic product, use and formulation thereof |
| JP2006528185A (ja) | 2003-07-21 | 2006-12-14 | アドバンシス ファーマスーティカル コーポレイション | 抗生物質製剤、その使用法及び作成方法 |
| WO2005016311A1 (en) | 2003-08-11 | 2005-02-24 | Advancis Pharmaceutical Corporation | Robust pellet |
| AU2004264356B2 (en) | 2003-08-12 | 2011-01-27 | Shionogi, Inc. | Antibiotic product, use and formulation thereof |
| JP5686494B2 (ja) | 2003-08-29 | 2015-03-18 | シオノギ インコーポレイテッド | 抗生物質製剤、その使用法及び作成方法 |
| EP1663169A4 (en) | 2003-09-15 | 2010-11-24 | Middlebrook Pharmaceuticals In | ANTIBIOTICS, ITS USE AND FORMULATION |
| WO2006014427A1 (en) | 2004-07-02 | 2006-02-09 | Advancis Pharmaceutical Corporation | Tablet for pulsed delivery |
| MX2007008162A (es) * | 2005-01-06 | 2007-07-24 | Cv Therapeutics Inc | Formulaciones farmaceuticas de liberacion prolongada que contienen ranolazina. |
| US8357394B2 (en) | 2005-12-08 | 2013-01-22 | Shionogi Inc. | Compositions and methods for improved efficacy of penicillin-type antibiotics |
| US8778924B2 (en) | 2006-12-04 | 2014-07-15 | Shionogi Inc. | Modified release amoxicillin products |
| US8299052B2 (en) | 2006-05-05 | 2012-10-30 | Shionogi Inc. | Pharmaceutical compositions and methods for improved bacterial eradication |
| CN100455288C (zh) * | 2006-06-26 | 2009-01-28 | 哈药集团制药总厂 | 一种盐酸雷诺嗪制剂配方 |
| US20080031947A1 (en) * | 2006-07-24 | 2008-02-07 | Cima Labs Inc. | Orally dissolvable/disintegrable lyophilized dosage forms containing protected |
| CA2678272A1 (en) * | 2007-02-13 | 2008-10-02 | Cv Therapeutics, Inc. | Use of ranolazine for the treatment of cardiovascular diseases |
| US20090111826A1 (en) * | 2007-02-13 | 2009-04-30 | Louis Lange | Use of ranolazine for the treatment of cardiovascular diseases |
| EP2117549A1 (en) * | 2007-02-13 | 2009-11-18 | CV Therapeutics Inc. | Use of ranolazine for the treatment of coronary microvascular diseases |
| JP2010518171A (ja) * | 2007-02-13 | 2010-05-27 | ギリアード・パロ・アルト・インコーポレイテッド | 非冠微小血管疾患の処置のためのラノラジンの使用 |
| WO2008109175A1 (en) * | 2007-03-07 | 2008-09-12 | Concert Pharmaceuticals, Inc. | Deuterated piperazine derivatives as anti-anginal compounds |
| WO2008116083A1 (en) * | 2007-03-22 | 2008-09-25 | Cv Therapeutics, Inc. | Use of ranolazine for elevated brain-type natriuretic peptide |
| JP2010528112A (ja) * | 2007-05-31 | 2010-08-19 | ギリアード・パロ・アルト・インコーポレイテッド | 糖尿病を治療する方法 |
| CA2689633A1 (en) * | 2007-05-31 | 2008-12-11 | Cv Therapeutics, Inc. | Use of ranolazine for elevated brain-type natriuretic peptide |
| RU2442585C2 (ru) * | 2007-05-31 | 2012-02-20 | Си Ви Терапьютикс, Инк. | Способ лечения диабета |
| KR20100047190A (ko) * | 2007-06-13 | 2010-05-07 | 오스펙스 파마슈티칼스, 인코포레이티드 | 치환 피페라진 |
| US20090012103A1 (en) * | 2007-07-05 | 2009-01-08 | Matthew Abelman | Substituted heterocyclic compounds |
| BRPI0908428A2 (pt) * | 2008-02-06 | 2015-12-08 | Gilead Sciences Inc | uso de ranozalina para tratar a dor. |
| MX2011012140A (es) * | 2009-05-14 | 2012-02-28 | Gilead Sciences Inc | Ranolazina para el tratamiento de problemas del snc. |
| NO3175985T3 (enExample) | 2011-07-01 | 2018-04-28 | ||
| WO2013043925A1 (en) | 2011-09-21 | 2013-03-28 | Gilead Sciences, Inc. | Sodium channel blockers reduce glucagon secretion |
| TW201717919A (zh) | 2015-07-02 | 2017-06-01 | 國際藥品股份公司 | 雷諾多重壓縮錠劑 |
| WO2018001582A1 (en) | 2016-06-30 | 2018-01-04 | Interquim, S.A. | Ranolazine multiple compressed tablets |
| JP2023507626A (ja) | 2019-12-16 | 2023-02-24 | テナックス・セラピューティクス，インコーポレイテッド | 駆出率が保たれた心不全を伴う肺高血圧症（ＰＨ－ＨＦ－ｐＥＦ）を治療するためのレボシメンダン |
| US12569481B2 (en) | 2020-06-12 | 2026-03-10 | Vanderbilt University | Methods of treatment for gastrointestinal motility disorders |
| EP4456897A4 (en) | 2021-12-31 | 2025-12-10 | Tenax Therapeutics Inc | ORAL FORMULATIONS OF LEVOSIMENDAN FOR THE TREATMENT OF PULMONARY HYPERTENSION WITH HEART FAILURE AND PRESERVED EJECTION FRACTION |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4567264A (en) * | 1983-05-18 | 1986-01-28 | Syntex (U.S.A.) Inc. | Cardioselective aryloxy- and arylthio- hydroxypropylene-piperazinyl acetanilides which affect calcium entry |
| IL81419A0 (en) * | 1986-01-30 | 1987-08-31 | Syntex Inc | Long acting sustained release pharmaceutical compositions containing dihydropyridines and their preparation |
| ES2177601T3 (es) * | 1989-06-23 | 2002-12-16 | Syntex Llc | Ranolazina y pepeerazinas relacionadas para uso en el tratamiento de estados de choque. . |
| US5209933A (en) | 1990-01-10 | 1993-05-11 | Syntex (U.S.A.) Inc. | Long acting calcium channel blocker composition |
| JPH06199657A (ja) * | 1992-12-10 | 1994-07-19 | Sumitomo Pharmaceut Co Ltd | 徐放性製剤 |
| US5455045A (en) * | 1993-05-13 | 1995-10-03 | Syntex (U.S.A.) Inc. | High dose formulations |
| JPH09188617A (ja) * | 1996-01-08 | 1997-07-22 | Pola Chem Ind Inc | 徐放性医薬組成物 |
| US6303607B1 (en) * | 1998-09-10 | 2001-10-16 | Cv Therapeutics, Inc. | Method for administering a sustained release ranolanolazine formulation |
| US6479496B1 (en) * | 1998-09-10 | 2002-11-12 | Cv Therapeutics, Inc. | Methods for treating angina with ranolazine |
| JP2000336032A (ja) * | 1999-05-26 | 2000-12-05 | Kissei Pharmaceut Co Ltd | ピペラジンアセトアミド誘導体を含有する徐放性経口医薬品組成物 |
-
2000
- 2000-03-08 US US09/520,932 patent/US6479496B1/en not_active Expired - Lifetime
-
2001
- 2001-03-07 CA CA002402222A patent/CA2402222C/en not_active Expired - Lifetime
- 2001-03-07 WO PCT/US2001/007287 patent/WO2001066093A2/en not_active Ceased
- 2001-03-07 CZ CZ20022996A patent/CZ20022996A3/cs unknown
- 2001-03-07 BR BR0109091-7A patent/BR0109091A/pt not_active Application Discontinuation
- 2001-03-07 AU AU2001240092A patent/AU2001240092B8/en not_active Revoked
- 2001-03-07 IL IL15157501A patent/IL151575A0/xx unknown
- 2001-03-07 MX MXPA02008654A patent/MXPA02008654A/es active IP Right Grant
- 2001-03-07 AU AU4009201A patent/AU4009201A/xx active Pending
- 2001-03-07 HU HU0204409A patent/HUP0204409A3/hu unknown
- 2001-03-07 PL PL01357273A patent/PL357273A1/xx not_active Application Discontinuation
- 2001-03-07 CN CNB018061850A patent/CN1323664C/zh not_active Expired - Lifetime
- 2001-03-07 NZ NZ521292A patent/NZ521292A/en not_active IP Right Cessation
- 2001-03-07 JP JP2001564746A patent/JP4108980B2/ja not_active Expired - Lifetime
- 2001-03-07 EP EP01914738A patent/EP1263439A2/en not_active Withdrawn
- 2001-03-07 RU RU2002126615/14A patent/RU2002126615A/ru unknown
-
2002
- 2002-09-06 NO NO20024270A patent/NO20024270L/no not_active Application Discontinuation
-
2007
- 2007-09-20 JP JP2007243731A patent/JP2008069159A/ja active Pending
-
2008
- 2008-09-03 AU AU2008212005A patent/AU2008212005A1/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CA2402222A1 (en) | 2001-09-13 |
| HK1058003A1 (en) | 2004-04-30 |
| NO20024270L (no) | 2002-11-06 |
| BR0109091A (pt) | 2005-02-15 |
| IL151575A0 (en) | 2003-04-10 |
| AU4009201A (en) | 2001-09-17 |
| PL357273A1 (en) | 2004-07-26 |
| RU2002126615A (ru) | 2004-03-20 |
| MXPA02008654A (es) | 2004-09-06 |
| WO2001066093A2 (en) | 2001-09-13 |
| JP2008069159A (ja) | 2008-03-27 |
| EP1263439A2 (en) | 2002-12-11 |
| JP2003525896A (ja) | 2003-09-02 |
| US6479496B1 (en) | 2002-11-12 |
| CN1443069A (zh) | 2003-09-17 |
| HUP0204409A3 (en) | 2005-04-28 |
| CZ20022996A3 (cs) | 2003-09-17 |
| CN1323664C (zh) | 2007-07-04 |
| HUP0204409A2 (en) | 2003-05-28 |
| AU2001240092B2 (en) | 2004-10-14 |
| JP4108980B2 (ja) | 2008-06-25 |
| AU2008212005A1 (en) | 2008-09-25 |
| NO20024270D0 (no) | 2002-09-06 |
| CA2402222C (en) | 2009-11-03 |
| AU2001240092B8 (en) | 2004-12-02 |
| WO2001066093A3 (en) | 2002-03-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU760435B2 (en) | Sustained release ranolazine formulations | |
| CA2402222C (en) | Sustained release ranolazine formulations | |
| AU2001240092A1 (en) | Sustained release ranolazine formulations | |
| US20020052377A1 (en) | Method for treating angina | |
| HK1075415A (en) | Sustained release ranolazine formulations |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PSEA | Patent sealed | ||
| ASS | Change of ownership |
Owner name: ROCHE PALO ALTO, US Free format text: OLD OWNER(S): CV THERAPEUTICS, INC. |
|
| RENW | Renewal (renewal fees accepted) | ||
| RENW | Renewal (renewal fees accepted) |
Free format text: PATENT RENEWED FOR 7 YEARS UNTIL 07 MAR 2021 BY COMPUTER PACKAGES INC Effective date: 20140328 |
|
| ASS | Change of ownership |
Owner name: GILEAD SCIENCES, INC., US Effective date: 20180328 |
|
| EXPY | Patent expired |