DK174918B1 - Fremgangsmåde til fremstilling af stabile nicorandilpræparater - Google Patents
Fremgangsmåde til fremstilling af stabile nicorandilpræparater Download PDFInfo
- Publication number
- DK174918B1 DK174918B1 DK198700191A DK19187A DK174918B1 DK 174918 B1 DK174918 B1 DK 174918B1 DK 198700191 A DK198700191 A DK 198700191A DK 19187 A DK19187 A DK 19187A DK 174918 B1 DK174918 B1 DK 174918B1
- Authority
- DK
- Denmark
- Prior art keywords
- nicorandil
- acid
- saturated
- tablet
- tablets
- Prior art date
Links
- LBHIOVVIQHSOQN-UHFFFAOYSA-N nicorandil Chemical compound [O-][N+](=O)OCCNC(=O)C1=CC=CN=C1 LBHIOVVIQHSOQN-UHFFFAOYSA-N 0.000 title claims description 63
- 229960002497 nicorandil Drugs 0.000 title claims description 63
- 238000000034 method Methods 0.000 title claims description 21
- 238000002360 preparation method Methods 0.000 title claims description 18
- 239000000203 mixture Substances 0.000 claims description 38
- 229920006395 saturated elastomer Polymers 0.000 claims description 18
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 claims description 16
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 15
- 235000021355 Stearic acid Nutrition 0.000 claims description 13
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 13
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- 239000008117 stearic acid Substances 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000001931 aliphatic group Chemical group 0.000 claims description 9
- 150000007524 organic acids Chemical class 0.000 claims description 9
- 235000021314 Palmitic acid Nutrition 0.000 claims description 8
- GOQYKNQRPGWPLP-UHFFFAOYSA-N n-heptadecyl alcohol Natural products CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 claims description 8
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 7
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 claims description 3
- 235000005985 organic acids Nutrition 0.000 claims description 3
- 229960000541 cetyl alcohol Drugs 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims description 2
- 150000002311 glutaric acids Chemical class 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000003826 tablet Substances 0.000 description 50
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 26
- 239000008187 granular material Substances 0.000 description 14
- 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 13
- 229930195725 Mannitol Natural products 0.000 description 13
- 239000001530 fumaric acid Substances 0.000 description 13
- 239000000594 mannitol Substances 0.000 description 13
- 235000010355 mannitol Nutrition 0.000 description 13
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 13
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 12
- 235000013539 calcium stearate Nutrition 0.000 description 12
- 239000008116 calcium stearate Substances 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- -1 nitrate ester Chemical class 0.000 description 12
- 239000000843 powder Substances 0.000 description 12
- 239000004698 Polyethylene Substances 0.000 description 10
- 229920000573 polyethylene Polymers 0.000 description 10
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 10
- 229920002261 Corn starch Polymers 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000008120 corn starch Substances 0.000 description 9
- 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 8
- 239000008101 lactose Substances 0.000 description 8
- 239000007916 tablet composition Substances 0.000 description 8
- 239000002775 capsule Substances 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000002245 particle Substances 0.000 description 7
- 238000003825 pressing Methods 0.000 description 7
- 238000013112 stability test Methods 0.000 description 7
- 238000005303 weighing Methods 0.000 description 7
- 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 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 235000019359 magnesium stearate Nutrition 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 5
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 5
- 239000004570 mortar (masonry) Substances 0.000 description 5
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 5
- 229960004889 salicylic acid Drugs 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 239000001993 wax Substances 0.000 description 4
- 229940084030 carboxymethylcellulose calcium Drugs 0.000 description 3
- 229920002678 cellulose Polymers 0.000 description 3
- 239000001913 cellulose Substances 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 238000007922 dissolution test Methods 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011812 mixed powder Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 235000001465 calcium Nutrition 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 2
- 229940105329 carboxymethylcellulose Drugs 0.000 description 2
- 239000004203 carnauba wax Substances 0.000 description 2
- 229940082483 carnauba wax Drugs 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 239000003925 fat Substances 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
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- FNAQSUUGMSOBHW-UHFFFAOYSA-H calcium citrate Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O FNAQSUUGMSOBHW-UHFFFAOYSA-H 0.000 description 1
- 239000001354 calcium citrate Substances 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- ASXJQLNITQPRKN-UHFFFAOYSA-L calcium octadecanoate chloride Chemical compound C(CCCCCCCCCCCCCCCCC)(=O)[O-].[Ca+2].[Cl-] ASXJQLNITQPRKN-UHFFFAOYSA-L 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 239000000306 component Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000019700 dicalcium phosphate Nutrition 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 230000004217 heart function Effects 0.000 description 1
- 229920003132 hydroxypropyl methylcellulose phthalate Polymers 0.000 description 1
- 229940031704 hydroxypropyl methylcellulose phthalate Drugs 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000010030 laminating Methods 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 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
- A61K9/20—Pills, tablets, discs, rods
-
- 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
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/455—Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP772286 | 1986-01-17 | ||
| JP772286 | 1986-01-17 | ||
| JP6185686 | 1986-03-19 | ||
| JP6185686 | 1986-03-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK19187D0 DK19187D0 (da) | 1987-01-15 |
| DK19187A DK19187A (da) | 1987-07-18 |
| DK174918B1 true DK174918B1 (da) | 2004-02-23 |
Family
ID=26342067
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK198700191A DK174918B1 (da) | 1986-01-17 | 1987-01-15 | Fremgangsmåde til fremstilling af stabile nicorandilpræparater |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4822808A (cs) |
| EP (1) | EP0230932B1 (cs) |
| KR (1) | KR940000232B1 (cs) |
| CN (1) | CN1009525B (cs) |
| AR (1) | AR241514A1 (cs) |
| AU (1) | AU591958B2 (cs) |
| CA (1) | CA1285486C (cs) |
| CS (1) | CS276587B6 (cs) |
| DE (1) | DE3769662D1 (cs) |
| DK (1) | DK174918B1 (cs) |
| EG (1) | EG18088A (cs) |
| ES (1) | ES2054623T3 (cs) |
| FI (1) | FI87043C (cs) |
| GR (1) | GR3002288T3 (cs) |
| HK (1) | HK66193A (cs) |
| HU (1) | HU196705B (cs) |
| MX (1) | MX167912B (cs) |
| NO (1) | NO173590C (cs) |
| NZ (1) | NZ218917A (cs) |
| PT (1) | PT84124B (cs) |
| SG (1) | SG64893G (cs) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5637322A (en) * | 1992-11-06 | 1997-06-10 | Japan Tobacco Inc. | Method for producing composition for solid medicine |
| IT1293835B1 (it) * | 1997-08-08 | 1999-03-10 | Foscama Biomed Chim Farma | Composizioni farmaceutiche orali in forma solida a cessione modulata contenenti nicorandil e procedimento per la loro preparazione |
| ATE308342T1 (de) * | 1997-08-08 | 2005-11-15 | Chugai Pharmaceutical Co Ltd | Arzneimittel gegen diabetes-komplikationen |
| AU748359B2 (en) * | 1998-05-15 | 2002-06-06 | Chugai Seiyaku Kabushiki Kaisha | Controlled-release formulations |
| AU4841700A (en) | 1999-05-12 | 2000-11-21 | Nitromed, Inc. | Nitrosated and nitrosylated potassium channel activators, compositions and methods of use |
| TWI324074B (en) * | 2001-10-09 | 2010-05-01 | Bristol Myers Squibb Co | Flashmelt oral dosage formulation |
| FR2872705B1 (fr) * | 2004-07-08 | 2008-07-18 | Aventis Pharma Sa | Compositions contenant du nicorandil, procede de preparation et utilisation |
| WO2008112227A1 (en) * | 2007-03-12 | 2008-09-18 | Reliant Pharmaceuticals, Inc. | Treatment with nicorandil and omega-3 fatty acids, and a combination product thereof |
| SI2098249T1 (sl) * | 2008-03-05 | 2013-02-28 | Rivopharm Sa | Nosilci nikorandila s povečano stabilnostjo |
| KR20100007082A (ko) * | 2008-07-11 | 2010-01-22 | 주식회사 엘지생명과학 | 니코란딜을 포함하는 서방성 제제 |
| CN102186474A (zh) * | 2008-08-14 | 2011-09-14 | 杏林制药株式会社 | 稳定的医药组合物 |
| ES2768651T3 (es) | 2013-04-25 | 2020-06-23 | Kyorin Seiyaku Kk | Composición farmacéutica sólida |
| CN110123749B (zh) * | 2019-06-03 | 2022-01-25 | 太阳升(亳州)生物医药科技有限公司 | 尼可地尔脂微球制剂及其制备方法 |
| CN111574441B (zh) * | 2020-05-26 | 2021-12-31 | 中国科学院上海药物研究所 | 一种尼可地尔与水杨酸的共晶及其制备方法和应用 |
| CN115429763B (zh) * | 2021-06-02 | 2024-01-02 | 北京四环科宝制药股份有限公司 | 尼可地尔片剂及其制备方法 |
| CN114732792A (zh) * | 2022-03-25 | 2022-07-12 | 北京诺康达医药科技股份有限公司 | 一种尼可地尔口腔崩解片及其制备方法 |
| CN115317456A (zh) * | 2022-08-17 | 2022-11-11 | 北京科源创欣科技有限公司 | 一种尼可地尔片组合物及其制备方法 |
| CN115282123B (zh) * | 2022-09-13 | 2023-11-03 | 南京比逊医药科技有限公司 | 一种稳定的尼可地尔制剂的制备方法 |
| CN117547534B (zh) * | 2023-11-10 | 2024-07-12 | 江南大学 | 尼可地尔缓释制剂及其制备方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3168438A (en) * | 1962-08-09 | 1965-02-02 | Synergistics Inc | Vasodilation by nitric acid ester derivatives of nicotinic acid |
| US3332848A (en) * | 1963-07-10 | 1967-07-25 | Hoffmann La Roche | Microcrystalline cellulose with starch in niacinamide ascorbic acid tablet granulations |
| US4200640A (en) * | 1976-04-02 | 1980-04-29 | Chugai Seiyaku Kabushiki Kaisha | Nitric ester of N-(2-hydroxyethyl)nicotinamide and pharmaceutical use |
| JPS599539B2 (ja) * | 1979-11-13 | 1984-03-03 | 日本化薬株式会社 | ニトログリセリン水溶液及びその製造法 |
| US4490377A (en) * | 1980-07-29 | 1984-12-25 | Syntex (U.S.A.) Inc. | Acid stabilized compositions of thieno-pyridine derived compounds |
| JPS57145659A (en) * | 1981-03-06 | 1982-09-08 | Chugai Pharmaceutical Co Ltd | Production of tablet |
| US4382091A (en) * | 1981-04-30 | 1983-05-03 | Syntex (U.S.A.) Inc. | Stabilization of 1-substituted imidazole derivatives in talc |
| JPS5839618A (ja) * | 1981-09-04 | 1983-03-08 | Chugai Pharmaceut Co Ltd | 持続性積層錠剤 |
| DE3244178A1 (de) * | 1982-11-30 | 1984-05-30 | Bayer Ag, 5090 Leverkusen | 1,4-dihydropyridinderivate, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| DE3421468A1 (de) * | 1984-06-08 | 1985-12-19 | Dr. Rentschler Arzneimittel Gmbh & Co, 7958 Laupheim | Lipidnanopellets als traegersystem fuer arzneimittel zur peroralen anwendung |
| JPH0653658B2 (ja) * | 1984-12-17 | 1994-07-20 | 中外製薬株式会社 | 安定な錠剤の製造法 |
| US5188840A (en) * | 1985-09-26 | 1993-02-23 | Chugai Seiyaku Kabushiki Kaisha | Slow-release pharmaceutical agent |
-
1986
- 1986-12-31 KR KR1019860011645A patent/KR940000232B1/ko not_active Expired - Lifetime
-
1987
- 1987-01-13 EG EG19/87A patent/EG18088A/xx active
- 1987-01-13 NZ NZ218917A patent/NZ218917A/xx unknown
- 1987-01-14 CA CA000527319A patent/CA1285486C/en not_active Expired - Lifetime
- 1987-01-14 FI FI870131A patent/FI87043C/fi not_active IP Right Cessation
- 1987-01-15 CS CS87282A patent/CS276587B6/cs not_active IP Right Cessation
- 1987-01-15 AR AR87306490A patent/AR241514A1/es active
- 1987-01-15 DK DK198700191A patent/DK174918B1/da not_active IP Right Cessation
- 1987-01-16 CN CN87100285A patent/CN1009525B/zh not_active Expired
- 1987-01-16 DE DE8787100549T patent/DE3769662D1/de not_active Expired - Lifetime
- 1987-01-16 AU AU67648/87A patent/AU591958B2/en not_active Expired
- 1987-01-16 HU HU87123A patent/HU196705B/hu unknown
- 1987-01-16 ES ES87100549T patent/ES2054623T3/es not_active Expired - Lifetime
- 1987-01-16 EP EP87100549A patent/EP0230932B1/en not_active Expired - Lifetime
- 1987-01-16 MX MX004957A patent/MX167912B/es unknown
- 1987-01-16 PT PT84124A patent/PT84124B/pt unknown
- 1987-01-19 NO NO870212A patent/NO173590C/no unknown
-
1988
- 1988-06-13 US US07/211,095 patent/US4822808A/en not_active Expired - Lifetime
-
1991
- 1991-07-10 GR GR91400993T patent/GR3002288T3/el unknown
-
1993
- 1993-05-18 SG SG648/93A patent/SG64893G/en unknown
- 1993-07-08 HK HK661/93A patent/HK66193A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| HUT44435A (en) | 1988-03-28 |
| FI87043C (fi) | 1992-11-25 |
| CA1285486C (en) | 1991-07-02 |
| FI87043B (fi) | 1992-08-14 |
| CN87100285A (zh) | 1987-08-19 |
| AR241514A1 (es) | 1992-08-31 |
| NO173590C (no) | 1994-01-05 |
| AU6764887A (en) | 1987-07-23 |
| EG18088A (en) | 1992-08-30 |
| FI870131L (fi) | 1987-07-18 |
| PT84124A (en) | 1987-02-01 |
| DK19187A (da) | 1987-07-18 |
| ES2054623T3 (es) | 1994-08-16 |
| SG64893G (en) | 1993-08-06 |
| EP0230932A3 (en) | 1987-12-09 |
| PT84124B (pt) | 1989-02-28 |
| EP0230932A2 (en) | 1987-08-05 |
| KR940000232B1 (ko) | 1994-01-12 |
| EP0230932B1 (en) | 1991-05-02 |
| US4822808A (en) | 1989-04-18 |
| CS8700282A2 (en) | 1991-07-16 |
| NO870212D0 (no) | 1987-01-19 |
| KR870006894A (ko) | 1987-08-13 |
| DE3769662D1 (de) | 1991-06-06 |
| HU196705B (en) | 1989-01-30 |
| DK19187D0 (da) | 1987-01-15 |
| MX167912B (es) | 1993-04-22 |
| NO870212L (no) | 1987-07-20 |
| GR3002288T3 (en) | 1992-12-30 |
| FI870131A0 (fi) | 1987-01-14 |
| CS276587B6 (en) | 1992-07-15 |
| NZ218917A (en) | 1989-10-27 |
| NO173590B (no) | 1993-09-27 |
| CN1009525B (zh) | 1990-09-12 |
| HK66193A (en) | 1993-07-16 |
| AU591958B2 (en) | 1989-12-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUP | Patent expired |