IE36016L - Nicotinic acid derivatives. - Google Patents
Nicotinic acid derivatives.Info
- Publication number
- IE36016L IE36016L IE711468A IE146871A IE36016L IE 36016 L IE36016 L IE 36016L IE 711468 A IE711468 A IE 711468A IE 146871 A IE146871 A IE 146871A IE 36016 L IE36016 L IE 36016L
- Authority
- IE
- Ireland
- Prior art keywords
- hydroxy
- nicotinic acid
- acid
- alkyl
- give
- Prior art date
Links
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 title abstract 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 abstract 6
- 229960003512 nicotinic acid Drugs 0.000 abstract 5
- 239000011664 nicotinic acid Substances 0.000 abstract 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 4
- 238000006243 chemical reaction Methods 0.000 abstract 4
- UEYQJQVBUVAELZ-UHFFFAOYSA-N 2-Hydroxynicotinic acid Chemical class OC(=O)C1=CC=CN=C1O UEYQJQVBUVAELZ-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 235000010288 sodium nitrite Nutrition 0.000 abstract 3
- IHLBCGVADAYUDV-UHFFFAOYSA-N 4-chloro-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC(=O)C1=C(Cl)C=CNC1=O IHLBCGVADAYUDV-UHFFFAOYSA-N 0.000 abstract 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 2
- -1 alkyl lithium Chemical compound 0.000 abstract 2
- 229910021529 ammonia Inorganic materials 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- VLGIIWGQCIFWPV-UHFFFAOYSA-N 2-amino-4-methylpyridine-3-carboxylic acid Chemical compound CC1=CC=NC(N)=C1C(O)=O VLGIIWGQCIFWPV-UHFFFAOYSA-N 0.000 abstract 1
- OOKFORLRLLVDOD-UHFFFAOYSA-N 2-amino-5-methylpyridine-3-carbonitrile Chemical compound CC1=CN=C(N)C(C#N)=C1 OOKFORLRLLVDOD-UHFFFAOYSA-N 0.000 abstract 1
- QWAPEIPRSXJCBK-UHFFFAOYSA-N 2-carbamoyl-4-methylpyridine-3-carboxylic acid Chemical compound C(=O)(O)C=1C(=NC=CC1C)C(=O)N QWAPEIPRSXJCBK-UHFFFAOYSA-N 0.000 abstract 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- ALJSJOYNRAYYSJ-UHFFFAOYSA-N 4-amino-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound NC=1C=CNC(=O)C=1C(O)=O ALJSJOYNRAYYSJ-UHFFFAOYSA-N 0.000 abstract 1
- LKXREDOIMHQPQO-UHFFFAOYSA-N 4-methylpyridine-2,3-dicarboxylic acid Chemical compound CC1=CC=NC(C(O)=O)=C1C(O)=O LKXREDOIMHQPQO-UHFFFAOYSA-N 0.000 abstract 1
- QMJIMNGWYFBQKB-UHFFFAOYSA-N 5-amino-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound NC1=CN=C(O)C(C(O)=O)=C1 QMJIMNGWYFBQKB-UHFFFAOYSA-N 0.000 abstract 1
- GKYJTSJLGDBJKC-UHFFFAOYSA-N 5-methyl-2-oxo-1h-pyridine-3-carbonitrile Chemical compound CC1=CN=C(O)C(C#N)=C1 GKYJTSJLGDBJKC-UHFFFAOYSA-N 0.000 abstract 1
- YFHKLJZXZABYPU-UHFFFAOYSA-N 6-bromo-2-oxo-1h-pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=C(Br)NC1=O YFHKLJZXZABYPU-UHFFFAOYSA-N 0.000 abstract 1
- 101000653791 Bos taurus Protein S100-A12 Proteins 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 abstract 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 abstract 1
- SFCMXMCBRUVDNL-UHFFFAOYSA-N OC1=C(C(=O)O)C(=CC=[N+]1[O-])[N+](=O)[O-] Chemical compound OC1=C(C(=O)O)C(=CC=[N+]1[O-])[N+](=O)[O-] SFCMXMCBRUVDNL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000005903 acid hydrolysis reaction Methods 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- ITQTTZVARXURQS-UHFFFAOYSA-N beta-methylpyridine Natural products CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 abstract 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 abstract 1
- DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 abstract 1
- 229940045803 cuprous chloride Drugs 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 230000000055 hyoplipidemic effect Effects 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- 229910001623 magnesium bromide Inorganic materials 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 235000001968 nicotinic acid Nutrition 0.000 abstract 1
- 230000020477 pH reduction Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 239000004291 sulphur dioxide Substances 0.000 abstract 1
- 235000010269 sulphur dioxide Nutrition 0.000 abstract 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
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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
- C07D213/84—Nitriles
- C07D213/85—Nitriles in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Abstract
1317239 2-Hydroxy-nicotinic acids F HOFFMANN-LA ROCHE & CO AG 23 Nov 1971 [23 Nov 1970 (2)] 54366/71 Heading C2C Novel 2-hydroxy-nicotinic acids of the general formula wherein R is a halogen atom in the 5- or 6- position, an amino group in the 4-position or a C 1-4 alkyl group in the 4- or 5-position, and base addition salts thereof are prepared (a) by base hydrolysis of a 2,6-dihalo-nicotinic acid at reflux temperature and acidification of the hydrolysis mixture to give a 6-halo-2-hydroxy-nicotinic acid, (b) by hydrogenation of 2-hydroxy-4- nitro-nicotinic acid-N-oxide to give 4-amino-2- hydroxy-nicotinic acid, (c) by reaction of 4- chloro-2-hydroxy-nicotinic acid with ammonia to give the product of (b), (d) by treatment of 4-chloro-2-hydroxy-nicotinic acid with a C 1-4 alkyl lithium or C 1-4 alkyl magnesium bromide to give a 2-hydroxy-4-C 1-4 alkyl-nicotinic acid, (e) by treatment of a 2-amino-4-C 1-4 alkylnicotinic acid with sodium nitrite and sulphuric acid to give a 2-hydroxy-4-C 1-4 alkyl-nicotinic acid, (f) by treatment of a 2-hydroxy-3-bromo- 5-C 1-4 alkyl-pyridine in an inert solvent with n-butyl lithium and carbon dioxide to give a 2 - hydroxy - 5 - C 1-4 alkyl - nicotinic acid, (g) by acid hydrolysis of a 2-hydroxy-3-cyano-5- C 1-4 alkyl-pyridine to give a 2-hydroxy-5-C 1-4 alkyl-nicotinic acid and (h) by treatment of 2- hydroxy-5-amino-nicotinic acid with sodium nitrite and hydrochloric acid/cuprous chloride or hydrobromic acid/cuprous bromide to give 5 - chloro- or bromo - 2 - hydroxy - nicotinic acid, followed optionally by salification of the product. 2 - Hydroxy - 3 - cyano - 5 - methyl - pyridine is prepared by reaction of 2-amino-3-bromo-5- 5-methyl-pyridine with cuprous cyanide and treatment of the resulting 2-amino-3-cyano-5- methyl-pyridine with sodium nitrite and sulphuric acid. 2 - Amino - 4 - methyl - nicotinic acid is prepared by reaction of 4-methylquinolinic acid with ammonia and reaction of the resulting 3 - carboxy - 4 - methyl - pyridine-2- carboxylic acid amide with aqueous sodium hydroxide and bromine, followed by sulphur dioxide. Pharmaceutical compositions having hypolipidemic activity comprise, as active ingredient, a 2-hydroxy-nicotinic acid of the above general formula or a pharmaceutically acceptable base addition salt thereof, in association with a compatible pharmaceutical carrier.
[GB1317239A]
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9213770A | 1970-11-23 | 1970-11-23 | |
| US9229670A | 1970-11-23 | 1970-11-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE36016L true IE36016L (en) | 1972-05-23 |
| IE36016B1 IE36016B1 (en) | 1976-07-21 |
Family
ID=26785310
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1468/71A IE36016B1 (en) | 1970-11-23 | 1971-11-19 | Nicotinic acid derivatives |
Country Status (12)
| Country | Link |
|---|---|
| AR (1) | AR192334A1 (en) |
| BE (1) | BE775641A (en) |
| CH (1) | CH558798A (en) |
| DE (1) | DE2157334A1 (en) |
| ES (1) | ES397243A1 (en) |
| FR (1) | FR2115357B1 (en) |
| GB (1) | GB1317239A (en) |
| HU (1) | HU163713B (en) |
| IE (1) | IE36016B1 (en) |
| IL (1) | IL38089A (en) |
| NL (1) | NL7115903A (en) |
| NO (1) | NO133894C (en) |
-
1971
- 1971-11-03 CH CH1612471A patent/CH558798A/en not_active IP Right Cessation
- 1971-11-08 IL IL38089A patent/IL38089A/en unknown
- 1971-11-18 DE DE19712157334 patent/DE2157334A1/en active Pending
- 1971-11-18 NL NL7115903A patent/NL7115903A/xx unknown
- 1971-11-18 NO NO714263A patent/NO133894C/no unknown
- 1971-11-19 IE IE1468/71A patent/IE36016B1/en unknown
- 1971-11-22 ES ES397243A patent/ES397243A1/en not_active Expired
- 1971-11-22 BE BE775641A patent/BE775641A/en unknown
- 1971-11-23 AR AR239196A patent/AR192334A1/en active
- 1971-11-23 FR FR7141921A patent/FR2115357B1/fr not_active Expired
- 1971-11-23 GB GB5436671A patent/GB1317239A/en not_active Expired
- 1971-11-23 HU HUHO1435A patent/HU163713B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU3556471A (en) | 1973-05-17 |
| IL38089A (en) | 1975-08-31 |
| GB1317239A (en) | 1973-05-16 |
| CH558798A (en) | 1975-02-14 |
| DE2157334A1 (en) | 1972-05-31 |
| FR2115357B1 (en) | 1974-10-18 |
| IL38089A0 (en) | 1972-01-27 |
| ES397243A1 (en) | 1975-04-16 |
| HU163713B (en) | 1973-10-27 |
| AR192334A1 (en) | 1973-02-14 |
| NO133894C (en) | 1976-07-14 |
| NO133894B (en) | 1976-04-05 |
| FR2115357A1 (en) | 1972-07-07 |
| IE36016B1 (en) | 1976-07-21 |
| NL7115903A (en) | 1972-05-25 |
| BE775641A (en) | 1972-05-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1234058A (en) | ||
| GB1307205A (en) | Isoindoline derivatives | |
| GB1294763A (en) | 3-oxo-2,3-dihydro-1,4-benzoxazine derivatives | |
| GB1382513A (en) | 1-pyridylalkyl-indole derivatives | |
| GB1467110A (en) | 4-phenyl-5-oxo-heptenoic acids | |
| GB1513320A (en) | N-propargyl-2-phenylamino-2-imidazolines | |
| IE36016B1 (en) | Nicotinic acid derivatives | |
| KR830007631A (en) | 2-pyridinecarboxamide derivatives and preparation method thereof | |
| GB1321424A (en) | N-phenyl-n-disubstituted aminoalkyl-2-amino indanes | |
| GB1448547A (en) | Derivative of phenylacetic acid | |
| ES8609208A1 (en) | A PROCESS FOR PREPARING p-AMINO PHENOLS BY ELECTROLYSIS. | |
| GB1384843A (en) | Benzofuran derivatives their preparation and compositions containing them | |
| GB1490289A (en) | Intermediates and production thereof for use in the preparation of 6-(2-phenyl-2-(guanylureidoacetamido)acetamido)penicillanic acid | |
| JPS591714B2 (en) | Process for producing isothiazoloisoquinoline derivatives | |
| GB1271767A (en) | Substituted arylpyridinecarboxylic acids and their derivatives | |
| GB1220750A (en) | New spiro-azatetramethylene derivatives | |
| Sammes et al. | Synthetic applications of N–N linked heterocycles. Part 16. Reactions between carbanions derived from carbon acids with p K a 7–14 and N-(2, 6-dimethyl-4-oxopyridin-1-yl) pyridinium tetrafluoroborate: synthesis of 4-substituted pyridines, and observation of pyridine ringopening reactions | |
| GB1192162A (en) | Derivatives of Tetrazolyl Alkanoic Acids | |
| IE34139B1 (en) | 4-phenyl-butric acid derivatives | |
| GB1465219A (en) | Process for the preparation of a phenyl alkonoic acid and its salts | |
| GB1285790A (en) | Acylaminopenicillanic acids and process for preparing them | |
| ES268522A1 (en) | A procedure for the production of new antranilic acids (Machine-translation by Google Translate, not legally binding) | |
| SE7600340L (en) | PROCEDURE FOR THE PREPARATION OF 2-AMINOIMIDAZOLIDE DERIVATIVES | |
| GB1511475A (en) | Hydrazinopyridazine derivatives having antihypertensive activity | |
| GB1335403A (en) | Pharmaceutical compositions containing benzofuran derivatives |