JPS5817463B2 - ニコチン酸アミド誘導体 - Google Patents
ニコチン酸アミド誘導体Info
- Publication number
- JPS5817463B2 JPS5817463B2 JP51036101A JP3610176A JPS5817463B2 JP S5817463 B2 JPS5817463 B2 JP S5817463B2 JP 51036101 A JP51036101 A JP 51036101A JP 3610176 A JP3610176 A JP 3610176A JP S5817463 B2 JPS5817463 B2 JP S5817463B2
- Authority
- JP
- Japan
- Prior art keywords
- nicotinic acid
- nitrate
- acid amide
- amide derivatives
- nicotinamide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical class NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 title claims description 6
- 229910002651 NO3 Inorganic materials 0.000 claims description 3
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 3
- 239000011570 nicotinamide Substances 0.000 claims description 3
- 229960003966 nicotinamide Drugs 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 235000005152 nicotinamide Nutrition 0.000 claims description 2
- 150000005480 nicotinamides Chemical class 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- LBHIOVVIQHSOQN-UHFFFAOYSA-N nicorandil Chemical compound [O-][N+](=O)OCCNC(=O)C1=CC=CN=C1 LBHIOVVIQHSOQN-UHFFFAOYSA-N 0.000 description 5
- -1 nicotinic acid ester Chemical class 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- CEZQWBVHIJYRGO-UHFFFAOYSA-N 3-(pyridin-3-ylmethoxy)propane-1,2-diol Chemical compound OCC(O)COCC1=CC=CN=C1 CEZQWBVHIJYRGO-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- MSYBLBLAMDYKKZ-UHFFFAOYSA-N hydron;pyridine-3-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=CN=C1 MSYBLBLAMDYKKZ-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000010446 mirabilite Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 208000031225 myocardial ischemia Diseases 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 2
- RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
- 230000000304 vasodilatating effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UKVBWDYMOLOAKV-UHFFFAOYSA-N 2-(2-hydroxyethylamino)ethanol;nitric acid Chemical compound O[N+]([O-])=O.OCCNCCO UKVBWDYMOLOAKV-UHFFFAOYSA-N 0.000 description 1
- OKZKZRACAIQAQK-UHFFFAOYSA-N 2-aminoethanol;nitric acid Chemical compound NCCO.O[N+]([O-])=O.O[N+]([O-])=O OKZKZRACAIQAQK-UHFFFAOYSA-N 0.000 description 1
- WAFNMNCIAQAQJU-UHFFFAOYSA-N 2-aminoethanol;nitric acid Chemical compound NCCO.O[N+]([O-])=O WAFNMNCIAQAQJU-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 239000004004 anti-anginal agent Substances 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940124345 antianginal agent Drugs 0.000 description 1
- QVMUMWQPPZZURQ-UHFFFAOYSA-N benzene;ethanol Chemical compound CCO.CCO.C1=CC=CC=C1 QVMUMWQPPZZURQ-UHFFFAOYSA-N 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000005923 long-lasting effect Effects 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SJZLOWYUGKIWAK-UHFFFAOYSA-N n-(2-hydroxyethyl)pyridine-3-carboxamide Chemical class OCCNC(=O)C1=CC=CN=C1 SJZLOWYUGKIWAK-UHFFFAOYSA-N 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- FCOXEIQHEDEXKV-UHFFFAOYSA-N nitric acid;pyridine-3-carboxamide Chemical compound O[N+]([O-])=O.NC(=O)C1=CC=CN=C1 FCOXEIQHEDEXKV-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 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
- 238000011282 treatment Methods 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (28)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP51036101A JPS5817463B2 (ja) | 1976-04-02 | 1976-04-02 | ニコチン酸アミド誘導体 |
| AU23532/77A AU509591B2 (en) | 1976-04-02 | 1977-03-23 | Pyridine derivatives |
| DK128277A DK145608C (da) | 1976-04-02 | 1977-03-23 | Analogifremgangsmaade til fremstilling af salpetersyreesteren af n-(2-hydroxyethyl)nicotinamid |
| GB1254177A GB1562962A (en) | 1976-04-02 | 1977-03-24 | Nicotinamide derivatives processes for producting the same and pharmaceutical compositions containing the same |
| CA274,696A CA1088944A (en) | 1976-04-02 | 1977-03-24 | Nitric ester of n-(2-hydroxyethyl)nicotinamide and a process for the preparation of same |
| MX775593U MX5534E (es) | 1976-04-02 | 1977-03-30 | Procedimiento para la preparacion de derivados de nicotinamida |
| MX1052777U MX7103E (es) | 1976-04-02 | 1977-03-30 | Procedimiento para preparar derivados de nicotinamida |
| ZA00771976A ZA771976B (en) | 1976-04-02 | 1977-03-31 | Novel pyridine derivative,process for preparing the same and pharmaceutical composition containing the same |
| ES457421A ES457421A1 (es) | 1976-04-02 | 1977-03-31 | Un procedimiento para la preparacion de nuevos derivados de piridina. |
| CS772189A CS228104B2 (en) | 1976-04-02 | 1977-04-01 | Preparation of esters of nitric acid and n-/2-hydroxyethyl/nicotinamides |
| FI771024A FI66598C (fi) | 1976-04-02 | 1977-04-01 | Foerfarande foer framstaellning av terapeutiskt anvaendbara sapetersyraestrar av n-(hydroxialkyl)pyridinkarboxamidderiv at |
| AR267099A AR217423A1 (es) | 1976-04-02 | 1977-04-01 | Procedimiento de preparacion de esteres nitricos de n-(2-hidroxietil)-nicotinamida |
| CH415377A CH633535A5 (en) | 1976-04-02 | 1977-04-01 | Process for the preparation of pyridine derivatives. |
| SU772467501A SU999965A3 (ru) | 1976-04-02 | 1977-04-01 | Способ получени эфира азотной кислоты N-/2-оксиэтил/-никотинамида или его солей |
| DE2714713A DE2714713C3 (de) | 1976-04-02 | 1977-04-01 | Salpetersäureester von N-(2-HydroxyäthyO-nicotinamid, Verfahren zu dessen Herstellung und Arzneimittel |
| SE7703868A SE436029B (sv) | 1976-04-02 | 1977-04-01 | Forfarande for framstellning av salpetersyraestern av n-(2-hydroxietyl)-nikotinamid |
| BE2055790A BE853144A (fr) | 1976-04-02 | 1977-04-01 | Derive nouveau de la pyridine, procede pour sa composition pharmaceutique contenant ce derive |
| NLAANVRAGE7703624,A NL176674C (nl) | 1976-04-02 | 1977-04-04 | Werkwijze ter bereiding van een geneesmiddel voor de behandeling van circulatiestoringen en werkwijze ter bereiding van de geneeskrachtige verbindingen. |
| AT235077A AT360532B (de) | 1976-04-02 | 1977-04-04 | Verfahren zur herstellung des neuen salpeter- saeureesters von n-(2-hydroxyaethyl)nicotinamid unter von desssen salzen |
| FR7710119A FR2346334A1 (fr) | 1976-04-02 | 1977-04-04 | Nouveaux derives de la pyridine, leur procede de preparation et leurs applications therapeutiques |
| HU77CU155A HU174118B (hu) | 1976-04-02 | 1977-09-01 | Sposob poluchenija novykh slozhnykh ehfirov i solej n-/2-gidroksi-ehtil/-niamido-azotnoj kisloty |
| AR271162A AR220907A1 (es) | 1976-04-02 | 1978-02-20 | Procedimiento de preparacion de esteres nitricos de n-(2-hidroxietil)nicotinamida |
| ES468462A ES468462A1 (es) | 1976-04-02 | 1978-03-31 | un procedimiento para la preparacion de nuevos derivados depiridina |
| SU782640400A SU942593A3 (ru) | 1976-04-02 | 1978-07-28 | Способ получени азотнокислого эфира N-/2-оксиэтил/ никотинамида или его солей |
| US05/940,194 US4200640A (en) | 1976-04-02 | 1978-09-07 | Nitric ester of N-(2-hydroxyethyl)nicotinamide and pharmaceutical use |
| CS787549A CS228111B2 (cs) | 1976-04-02 | 1978-11-20 | Způsob přípravy esteru kyseliny dusičné a N-(2-hydroxyethylJ-nikotinamidu |
| AT286979A AT360536B (de) | 1976-04-02 | 1979-04-17 | Verfahren zur herstellung des neuen salpeter- saeureesters von n-(2-hydroxyaethyl)nicotinamid und von dessen salzen |
| NL930042C NL930042I2 (nl) | 1976-04-02 | 1993-05-28 | Werkwijze ter bereiding van een geneesmiddel voor de behandeling van circulatiestoringen en werkwijze ter bereiding van de geneeskrachtige verbindingen. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP51036101A JPS5817463B2 (ja) | 1976-04-02 | 1976-04-02 | ニコチン酸アミド誘導体 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS52122373A JPS52122373A (en) | 1977-10-14 |
| JPS5817463B2 true JPS5817463B2 (ja) | 1983-04-07 |
Family
ID=12460366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP51036101A Expired JPS5817463B2 (ja) | 1976-04-02 | 1976-04-02 | ニコチン酸アミド誘導体 |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5817463B2 (cs) |
| BE (1) | BE853144A (cs) |
| CS (1) | CS228104B2 (cs) |
| SU (2) | SU999965A3 (cs) |
| ZA (1) | ZA771976B (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59192562U (ja) * | 1983-06-07 | 1984-12-20 | 四国化成工業株式会社 | 支柱 |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2020100598A (ja) | 2018-12-25 | 2020-07-02 | 公益財団法人応用生化学研究所 | レンバチニブ誘導体、並びにそれを用いた医薬研究用組成物及び腫瘍治療剤 |
-
1976
- 1976-04-02 JP JP51036101A patent/JPS5817463B2/ja not_active Expired
-
1977
- 1977-03-31 ZA ZA00771976A patent/ZA771976B/xx unknown
- 1977-04-01 CS CS772189A patent/CS228104B2/cs unknown
- 1977-04-01 BE BE2055790A patent/BE853144A/fr not_active IP Right Cessation
- 1977-04-01 SU SU772467501A patent/SU999965A3/ru active
-
1978
- 1978-07-28 SU SU782640400A patent/SU942593A3/ru active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59192562U (ja) * | 1983-06-07 | 1984-12-20 | 四国化成工業株式会社 | 支柱 |
Also Published As
| Publication number | Publication date |
|---|---|
| BE853144A (fr) | 1977-08-01 |
| CS228104B2 (en) | 1984-05-14 |
| SU999965A3 (ru) | 1983-02-23 |
| SU942593A3 (ru) | 1982-07-07 |
| ZA771976B (en) | 1978-03-29 |
| JPS52122373A (en) | 1977-10-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term | ||
| R154 | Certificate of patent or utility model (reissue) |
Free format text: JAPANESE INTERMEDIATE CODE: R154 |