IE36016B1 - Nicotinic acid derivatives - Google Patents
Nicotinic acid derivativesInfo
- Publication number
- IE36016B1 IE36016B1 IE1468/71A IE146871A IE36016B1 IE 36016 B1 IE36016 B1 IE 36016B1 IE 1468/71 A IE1468/71 A IE 1468/71A IE 146871 A IE146871 A IE 146871A IE 36016 B1 IE36016 B1 IE 36016B1
- 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)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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 IE36016L (en) | 1972-05-23 |
| IE36016B1 true 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 (enExample) |
| BE (1) | BE775641A (enExample) |
| CH (1) | CH558798A (enExample) |
| DE (1) | DE2157334A1 (enExample) |
| ES (1) | ES397243A1 (enExample) |
| FR (1) | FR2115357B1 (enExample) |
| GB (1) | GB1317239A (enExample) |
| HU (1) | HU163713B (enExample) |
| IE (1) | IE36016B1 (enExample) |
| IL (1) | IL38089A (enExample) |
| NL (1) | NL7115903A (enExample) |
| NO (1) | NO133894C (enExample) |
-
1971
- 1971-11-03 CH CH1612471A patent/CH558798A/xx not_active IP Right Cessation
- 1971-11-08 IL IL38089A patent/IL38089A/xx unknown
- 1971-11-18 NO NO714263A patent/NO133894C/no unknown
- 1971-11-18 NL NL7115903A patent/NL7115903A/xx unknown
- 1971-11-18 DE DE19712157334 patent/DE2157334A1/de active Pending
- 1971-11-19 IE IE1468/71A patent/IE36016B1/xx unknown
- 1971-11-22 ES ES397243A patent/ES397243A1/es not_active Expired
- 1971-11-22 BE BE775641A patent/BE775641A/xx unknown
- 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
- 1971-11-23 AR AR239196A patent/AR192334A1/es active
Also Published As
| Publication number | Publication date |
|---|---|
| NO133894C (enExample) | 1976-07-14 |
| NO133894B (enExample) | 1976-04-05 |
| IE36016L (en) | 1972-05-23 |
| DE2157334A1 (de) | 1972-05-31 |
| CH558798A (de) | 1975-02-14 |
| FR2115357B1 (enExample) | 1974-10-18 |
| FR2115357A1 (enExample) | 1972-07-07 |
| IL38089A0 (en) | 1972-01-27 |
| IL38089A (en) | 1975-08-31 |
| HU163713B (enExample) | 1973-10-27 |
| ES397243A1 (es) | 1975-04-16 |
| GB1317239A (en) | 1973-05-16 |
| AR192334A1 (es) | 1973-02-14 |
| BE775641A (fr) | 1972-05-23 |
| AU3556471A (en) | 1973-05-17 |
| NL7115903A (enExample) | 1972-05-25 |
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