FI66598C - Foerfarande foer framstaellning av terapeutiskt anvaendbara sapetersyraestrar av n-(hydroxialkyl)pyridinkarboxamidderiv at - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara sapetersyraestrar av n-(hydroxialkyl)pyridinkarboxamidderiv at Download PDFInfo
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- FI66598C FI66598C FI771024A FI771024A FI66598C FI 66598 C FI66598 C FI 66598C FI 771024 A FI771024 A FI 771024A FI 771024 A FI771024 A FI 771024A FI 66598 C FI66598 C FI 66598C
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- Prior art keywords
- compound
- solution
- nitric acid
- coronary
- effect
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- 150000001875 compounds Chemical class 0.000 claims description 85
- 238000000034 method Methods 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 11
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- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000005557 antagonist Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 229940127088 antihypertensive drug Drugs 0.000 description 1
- 210000000709 aorta Anatomy 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000037007 arousal Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 1
- 239000001639 calcium acetate Substances 0.000 description 1
- 235000011092 calcium acetate Nutrition 0.000 description 1
- 229960005147 calcium acetate Drugs 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000003205 diastolic effect Effects 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- SULWMEGSVQCTSK-UHFFFAOYSA-N diethyl hydrogen phosphite Chemical compound CCOP(O)OCC SULWMEGSVQCTSK-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BTYPWVDULNVBHU-UHFFFAOYSA-N disodium;dinitrate Chemical compound [Na+].[Na+].[O-][N+]([O-])=O.[O-][N+]([O-])=O BTYPWVDULNVBHU-UHFFFAOYSA-N 0.000 description 1
- 208000035475 disorder Diseases 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
- 230000005611 electricity Effects 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000010247 heart contraction Effects 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 230000004217 heart function Effects 0.000 description 1
- 208000031169 hemorrhagic disease Diseases 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 230000000622 irritating effect Effects 0.000 description 1
- 229940102253 isopropanolamine Drugs 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 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
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004660 morphological change Effects 0.000 description 1
- 230000004118 muscle contraction Effects 0.000 description 1
- UHAAFJWANJYDIS-UHFFFAOYSA-N n,n'-diethylmethanediimine Chemical compound CCN=C=NCC UHAAFJWANJYDIS-UHFFFAOYSA-N 0.000 description 1
- CDKFLTUOBAPNKV-UHFFFAOYSA-N n,n-bis(2-hydroxyethyl)pyridine-3-carboxamide Chemical compound OCCN(CCO)C(=O)C1=CC=CN=C1 CDKFLTUOBAPNKV-UHFFFAOYSA-N 0.000 description 1
- VMESOKCXSYNAKD-UHFFFAOYSA-N n,n-dimethylhydroxylamine Chemical compound CN(C)O VMESOKCXSYNAKD-UHFFFAOYSA-N 0.000 description 1
- SJZLOWYUGKIWAK-UHFFFAOYSA-N n-(2-hydroxyethyl)pyridine-3-carboxamide Chemical compound OCCNC(=O)C1=CC=CN=C1 SJZLOWYUGKIWAK-UHFFFAOYSA-N 0.000 description 1
- NBDWZSMXICVNGC-UHFFFAOYSA-N n-(2-hydroxypropyl)pyridine-3-carboxamide Chemical compound CC(O)CNC(=O)C1=CC=CN=C1 NBDWZSMXICVNGC-UHFFFAOYSA-N 0.000 description 1
- 230000014508 negative regulation of coagulation Effects 0.000 description 1
- LBHIOVVIQHSOQN-UHFFFAOYSA-N nicorandil Chemical compound [O-][N+](=O)OCCNC(=O)C1=CC=CN=C1 LBHIOVVIQHSOQN-UHFFFAOYSA-N 0.000 description 1
- 235000005152 nicotinamide Nutrition 0.000 description 1
- 239000011570 nicotinamide Substances 0.000 description 1
- 229960003966 nicotinamide Drugs 0.000 description 1
- 150000005480 nicotinamides Chemical class 0.000 description 1
- HVZWVEKIQMJYIK-UHFFFAOYSA-N nitryl chloride Chemical compound [O-][N+](Cl)=O HVZWVEKIQMJYIK-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000010355 oscillation Effects 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 210000005259 peripheral blood Anatomy 0.000 description 1
- 239000011886 peripheral blood Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000008327 renal blood flow Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000010414 supernatant solution Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3610176 | 1976-04-02 | ||
| JP51036101A JPS5817463B2 (ja) | 1976-04-02 | 1976-04-02 | ニコチン酸アミド誘導体 |
| JP8245876A JPS6052685B2 (ja) | 1976-07-13 | 1976-07-13 | 循環器疾患治療剤 |
| JP8245876 | 1976-07-13 | ||
| JP8352276A JPS539775A (en) | 1976-07-15 | 1976-07-15 | Pyridine derivatives and their preparation |
| JP8352276 | 1976-07-15 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI771024A7 FI771024A7 (da) | 1977-10-03 |
| FI66598B FI66598B (fi) | 1984-07-31 |
| FI66598C true FI66598C (fi) | 1984-11-12 |
Family
ID=27288973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI771024A FI66598C (fi) | 1976-04-02 | 1977-04-01 | Foerfarande foer framstaellning av terapeutiskt anvaendbara sapetersyraestrar av n-(hydroxialkyl)pyridinkarboxamidderiv at |
Country Status (13)
| Country | Link |
|---|---|
| AR (2) | AR217423A1 (da) |
| AT (1) | AT360532B (da) |
| AU (1) | AU509591B2 (da) |
| CA (1) | CA1088944A (da) |
| CH (1) | CH633535A5 (da) |
| DE (1) | DE2714713C3 (da) |
| DK (1) | DK145608C (da) |
| ES (2) | ES457421A1 (da) |
| FI (1) | FI66598C (da) |
| FR (1) | FR2346334A1 (da) |
| MX (1) | MX5534E (da) |
| NL (2) | NL176674C (da) |
| SE (1) | SE436029B (da) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO1986006960A2 (en) * | 1985-05-22 | 1986-12-04 | Beecham Group P.L.C. | Use of nicorandil or pinacidil for the treatment of peripheral vascular disease |
| AU3693789A (en) * | 1988-05-10 | 1989-11-29 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab) | New ophthalmic preparation for treating glaucoma |
| US4973565A (en) * | 1989-07-17 | 1990-11-27 | Corning Incorporated | Fluoroborosilicate glass and clad article |
| ZA91291B (en) * | 1990-01-16 | 1991-09-25 | Hoechst Ag | Di(nitroxyalkyl)amides of pyridine-2,4-and-2,5-dicarboxylic acids,a process for the preparation thereof,and the use thereof |
| WO2000067754A1 (en) * | 1999-05-12 | 2000-11-16 | Nitromed, Inc. | Nitrosated and nitrosylated potassium channel activators, compositions and methods of use |
| PL2307380T3 (pl) * | 2008-07-01 | 2013-01-31 | Univ Jagiellonski | Pochodne N’-nitroksyalkilonikotynamidu do leczenia chorób układu sercowo-naczyniowego |
| IT1403890B1 (it) | 2010-12-28 | 2013-11-08 | Procos Spa | Processo per la produzione di nicorandil |
-
1977
- 1977-03-23 DK DK128277A patent/DK145608C/da not_active IP Right Cessation
- 1977-03-23 AU AU23532/77A patent/AU509591B2/en not_active Expired
- 1977-03-24 CA CA274,696A patent/CA1088944A/en not_active Expired
- 1977-03-30 MX MX775593U patent/MX5534E/es unknown
- 1977-03-31 ES ES457421A patent/ES457421A1/es not_active Expired
- 1977-04-01 AR AR267099A patent/AR217423A1/es active
- 1977-04-01 DE DE2714713A patent/DE2714713C3/de not_active Expired
- 1977-04-01 SE SE7703868A patent/SE436029B/xx not_active IP Right Cessation
- 1977-04-01 FI FI771024A patent/FI66598C/fi not_active IP Right Cessation
- 1977-04-01 CH CH415377A patent/CH633535A5/de not_active IP Right Cessation
- 1977-04-04 AT AT235077A patent/AT360532B/de not_active IP Right Cessation
- 1977-04-04 NL NLAANVRAGE7703624,A patent/NL176674C/xx not_active IP Right Cessation
- 1977-04-04 FR FR7710119A patent/FR2346334A1/fr active Granted
-
1978
- 1978-02-20 AR AR271162A patent/AR220907A1/es active
- 1978-03-31 ES ES468462A patent/ES468462A1/es not_active Expired
-
1993
- 1993-05-28 NL NL930042C patent/NL930042I2/nl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2346334A1 (fr) | 1977-10-28 |
| FI771024A7 (da) | 1977-10-03 |
| ES457421A1 (es) | 1978-11-16 |
| FI66598B (fi) | 1984-07-31 |
| DE2714713A1 (de) | 1977-10-20 |
| DE2714713B2 (de) | 1980-02-21 |
| AU509591B2 (en) | 1980-05-15 |
| DK145608C (da) | 1983-07-11 |
| NL7703624A (nl) | 1977-10-04 |
| NL930042I1 (nl) | 1993-08-02 |
| CA1088944A (en) | 1980-11-04 |
| DE2714713C3 (de) | 1980-10-16 |
| NL176674B (nl) | 1984-12-17 |
| CH633535A5 (en) | 1982-12-15 |
| AT360532B (de) | 1981-01-12 |
| NL176674C (nl) | 1985-05-17 |
| FR2346334B1 (da) | 1980-02-01 |
| ATA235077A (de) | 1980-06-15 |
| SE7703868L (sv) | 1977-10-03 |
| AR217423A1 (es) | 1980-03-31 |
| DK145608B (da) | 1982-12-27 |
| DK128277A (da) | 1977-10-03 |
| NL930042I2 (nl) | 1993-09-16 |
| AU2353277A (en) | 1978-09-28 |
| SE436029B (sv) | 1984-11-05 |
| AR220907A1 (es) | 1980-12-15 |
| ES468462A1 (es) | 1979-10-01 |
| MX5534E (es) | 1983-09-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MA | Patent expired | ||
| MA | Patent expired |
Owner name: CHUGAI SEIYAKU KABUSHIKI KAISHA |