CS601987A2 - Method of pharmaceutical agent production for nicorandil endormication - Google Patents
Method of pharmaceutical agent production for nicorandil endormication Download PDFInfo
- Publication number
- CS601987A2 CS601987A2 CS876019A CS601987A CS601987A2 CS 601987 A2 CS601987 A2 CS 601987A2 CS 876019 A CS876019 A CS 876019A CS 601987 A CS601987 A CS 601987A CS 601987 A2 CS601987 A2 CS 601987A2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- nicorandil
- weight
- parts
- rubber
- acid
- Prior art date
Links
- 229960002497 nicorandil Drugs 0.000 title claims description 79
- LBHIOVVIQHSOQN-UHFFFAOYSA-N nicorandil Chemical compound [O-][N+](=O)OCCNC(=O)C1=CC=CN=C1 LBHIOVVIQHSOQN-UHFFFAOYSA-N 0.000 title claims description 78
- 238000000034 method Methods 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title description 4
- 239000008177 pharmaceutical agent Substances 0.000 title 1
- 239000000463 material Substances 0.000 claims description 36
- 125000001931 aliphatic group Chemical group 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 28
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- 239000008194 pharmaceutical composition Substances 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 19
- 229920001971 elastomer Polymers 0.000 claims description 18
- 239000005060 rubber Substances 0.000 claims description 18
- -1 alkyl radicals Chemical class 0.000 claims description 15
- 239000005062 Polybutadiene Substances 0.000 claims description 14
- 229920002857 polybutadiene Polymers 0.000 claims description 14
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 12
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 8
- 244000043261 Hevea brasiliensis Species 0.000 claims description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 8
- 239000013078 crystal Substances 0.000 claims description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 8
- 229920003052 natural elastomer Polymers 0.000 claims description 8
- 229920001194 natural rubber Polymers 0.000 claims description 8
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- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
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- VSKJLJHPAFKHBX-UHFFFAOYSA-N 2-methylbuta-1,3-diene;styrene Chemical compound CC(=C)C=C.C=CC1=CC=CC=C1.C=CC1=CC=CC=C1 VSKJLJHPAFKHBX-UHFFFAOYSA-N 0.000 claims 2
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 12
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- 125000004432 carbon atom Chemical group C* 0.000 description 7
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- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 6
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 6
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- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 4
- AOMUHOFOVNGZAN-UHFFFAOYSA-N N,N-bis(2-hydroxyethyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)N(CCO)CCO AOMUHOFOVNGZAN-UHFFFAOYSA-N 0.000 description 4
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
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- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 4
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- 231100000274 skin absorption Toxicity 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229920002367 Polyisobutene Polymers 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
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- AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
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- 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
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- 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
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- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 2
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- 239000003755 preservative agent Substances 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- FTBUKOLPOATXGV-UHFFFAOYSA-N propyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OCCC FTBUKOLPOATXGV-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 108700004121 sarkosyl Proteins 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920006132 styrene block copolymer Polymers 0.000 description 1
- LVLJBRFCYXMKCE-UHFFFAOYSA-N sulfo dodecanoate Chemical compound CCCCCCCCCCCC(=O)OS(O)(=O)=O LVLJBRFCYXMKCE-UHFFFAOYSA-N 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 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
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
- A61K9/7053—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained by reactions only involving carbon to carbon unsaturated bonds, e.g. polyvinyl, polyisobutylene, polystyrene
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
- A61K9/7069—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. polysiloxane, polyesters, polyurethane, polyethylene oxide
-
- 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
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7076—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising ingredients of undetermined constitution or reaction products thereof, e.g. rosin or other plant resins
Landscapes
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Dermatology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Botany (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19249286 | 1986-08-18 | ||
| JP19249386 | 1986-08-18 | ||
| JP8027687 | 1987-04-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS601987A2 true CS601987A2 (en) | 1990-08-14 |
Family
ID=27303257
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS876019A CS601987A2 (en) | 1986-08-18 | 1987-08-17 | Method of pharmaceutical agent production for nicorandil endormication |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US5211943A (da) |
| EP (1) | EP0260452B1 (da) |
| KR (1) | KR880002523A (da) |
| CN (1) | CN87105632A (da) |
| AR (2) | AR241513A1 (da) |
| AT (1) | ATA207887A (da) |
| AU (1) | AU7717587A (da) |
| BE (1) | BE1000477A3 (da) |
| CS (1) | CS601987A2 (da) |
| DE (1) | DE3782594T2 (da) |
| DK (1) | DK424987A (da) |
| ES (1) | ES2052528T3 (da) |
| FI (1) | FI873566A (da) |
| GR (1) | GR871267B (da) |
| HU (1) | HU200923B (da) |
| NO (1) | NO873423L (da) |
| NZ (1) | NZ221465A (da) |
| PT (1) | PT85543B (da) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2886446B2 (ja) * | 1994-03-03 | 1999-04-26 | 関西ペイント株式会社 | 塗膜保護用シート |
| US5925658A (en) * | 1995-03-02 | 1999-07-20 | Sankyo Company, Limited | Optically active thiazolidinone derivative |
| US5698217A (en) * | 1995-05-31 | 1997-12-16 | Minnesota Mining And Manufacturing Company | Transdermal drug delivery device containing a desiccant |
| WO2000061120A1 (fr) * | 1999-04-13 | 2000-10-19 | Hisamitsu Pharmaceutical Co., Inc. | Préparations destinées à être absorbées par voie percutanée |
| AU4841700A (en) | 1999-05-12 | 2000-11-21 | Nitromed, Inc. | Nitrosated and nitrosylated potassium channel activators, compositions and methods of use |
| CA3225065A1 (en) | 2021-07-10 | 2023-01-19 | Denny Johan Marijn Van Den Heuvel | Modified release nicorandil compound formulations |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4200640A (en) * | 1976-04-02 | 1980-04-29 | Chugai Seiyaku Kabushiki Kaisha | Nitric ester of N-(2-hydroxyethyl)nicotinamide and pharmaceutical use |
| JPS5910513A (ja) * | 1982-07-12 | 1984-01-20 | Nitto Electric Ind Co Ltd | 医薬製剤 |
| JPS60184010A (ja) * | 1984-03-02 | 1985-09-19 | Nitto Electric Ind Co Ltd | 経皮投与用医薬製剤 |
| GB2156215B (en) * | 1984-03-05 | 1988-03-02 | Nitto Electric Ind Co | Percutaneous absorption type adhesive pharmaceutical preparation |
| JPH0627068B2 (ja) * | 1984-09-22 | 1994-04-13 | 中外製薬株式会社 | 経皮薬剤 |
| JPS61103840A (ja) * | 1984-10-26 | 1986-05-22 | Nitto Electric Ind Co Ltd | 外皮投与用組成物 |
| 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 |
| US4690683A (en) * | 1985-07-02 | 1987-09-01 | Rutgers, The State University Of New Jersey | Transdermal varapamil delivery device |
-
1987
- 1987-08-12 GR GR871267A patent/GR871267B/el unknown
- 1987-08-14 AR AR87308440A patent/AR241513A1/es active
- 1987-08-14 US US07/086,319 patent/US5211943A/en not_active Expired - Fee Related
- 1987-08-14 NO NO873423A patent/NO873423L/no unknown
- 1987-08-14 BE BE8700910A patent/BE1000477A3/fr not_active IP Right Cessation
- 1987-08-14 DK DK424987A patent/DK424987A/da not_active Application Discontinuation
- 1987-08-17 NZ NZ221465A patent/NZ221465A/xx unknown
- 1987-08-17 EP EP87111906A patent/EP0260452B1/en not_active Expired - Lifetime
- 1987-08-17 DE DE8787111906T patent/DE3782594T2/de not_active Expired - Fee Related
- 1987-08-17 CS CS876019A patent/CS601987A2/cs unknown
- 1987-08-17 HU HU873692A patent/HU200923B/hu not_active IP Right Cessation
- 1987-08-17 ES ES87111906T patent/ES2052528T3/es not_active Expired - Lifetime
- 1987-08-17 PT PT85543A patent/PT85543B/pt unknown
- 1987-08-18 KR KR870009029A patent/KR880002523A/ko not_active Application Discontinuation
- 1987-08-18 CN CN198787105632A patent/CN87105632A/zh active Pending
- 1987-08-18 AU AU77175/87A patent/AU7717587A/en not_active Abandoned
- 1987-08-18 FI FI873566A patent/FI873566A/fi not_active Application Discontinuation
- 1987-08-18 AT AT2078/87A patent/ATA207887A/de not_active IP Right Cessation
-
1988
- 1988-04-15 AR AR310581A patent/AR240017A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| US5211943A (en) | 1993-05-18 |
| BE1000477A3 (fr) | 1988-12-20 |
| HUT45397A (en) | 1988-07-28 |
| GR871267B (en) | 1987-12-24 |
| CN87105632A (zh) | 1988-03-30 |
| EP0260452A1 (en) | 1988-03-23 |
| NO873423L (no) | 1988-02-19 |
| DE3782594D1 (de) | 1992-12-17 |
| NO873423D0 (no) | 1987-08-14 |
| ATA207887A (de) | 1990-08-15 |
| ES2052528T3 (es) | 1994-07-16 |
| AR240017A1 (es) | 1990-01-31 |
| NZ221465A (en) | 1989-12-21 |
| EP0260452B1 (en) | 1992-11-11 |
| FI873566A (fi) | 1988-02-19 |
| PT85543A (en) | 1987-09-01 |
| DK424987A (da) | 1988-02-19 |
| AU7717587A (en) | 1988-02-25 |
| AR241513A1 (es) | 1992-08-31 |
| PT85543B (en) | 1989-11-06 |
| HU200923B (en) | 1990-09-28 |
| KR880002523A (ko) | 1988-05-09 |
| FI873566A0 (fi) | 1987-08-18 |
| DK424987D0 (da) | 1987-08-14 |
| DE3782594T2 (de) | 1993-06-03 |
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