CA1054153A - PROCESS FOR THE PRODUCTION OF .alpha.(-2-(P-CHLOROPHENOXY)-ISOBUTYRYL)-.beta.-NICOTINOYL GLYCOL ESTER - Google Patents
PROCESS FOR THE PRODUCTION OF .alpha.(-2-(P-CHLOROPHENOXY)-ISOBUTYRYL)-.beta.-NICOTINOYL GLYCOL ESTERInfo
- Publication number
- CA1054153A CA1054153A CA234,142A CA234142A CA1054153A CA 1054153 A CA1054153 A CA 1054153A CA 234142 A CA234142 A CA 234142A CA 1054153 A CA1054153 A CA 1054153A
- Authority
- CA
- Canada
- Prior art keywords
- isobutyryl
- chlorophenoxy
- beta
- nicotinoyl
- glycol ester
- 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 title claims abstract description 25
- -1 GLYCOL ESTER Chemical class 0.000 title claims abstract description 24
- 238000000034 method Methods 0.000 title claims abstract description 23
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- 229960003750 ethyl chloride Drugs 0.000 claims abstract description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 45
- 238000006243 chemical reaction Methods 0.000 claims description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 7
- 238000004821 distillation Methods 0.000 claims description 6
- KFLRWGSAMLBHBV-UHFFFAOYSA-M sodium;pyridine-3-carboxylate Chemical compound [Na+].[O-]C(=O)C1=CC=CN=C1 KFLRWGSAMLBHBV-UHFFFAOYSA-M 0.000 claims description 4
- 235000001968 nicotinic acid Nutrition 0.000 claims description 3
- 239000011664 nicotinic acid Substances 0.000 claims description 3
- 229960003512 nicotinic acid Drugs 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 239000002798 polar solvent Substances 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 2
- 239000006227 byproduct Substances 0.000 abstract 1
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000007844 bleaching agent Substances 0.000 description 3
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000001348 alkyl chlorides Chemical class 0.000 description 2
- DLGYNVMUCSTYDQ-UHFFFAOYSA-N azane;pyridine Chemical compound N.C1=CC=NC=C1 DLGYNVMUCSTYDQ-UHFFFAOYSA-N 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 239000007937 lozenge Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 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
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CLWAXFZCVYJLLM-UHFFFAOYSA-N 1-chlorohexadecane Chemical compound CCCCCCCCCCCCCCCCCl CLWAXFZCVYJLLM-UHFFFAOYSA-N 0.000 description 1
- CEJKAKCQVUWNNA-UHFFFAOYSA-N 2-(4-chlorophenoxy)butanoic acid Chemical compound CCC(C(O)=O)OC1=CC=C(Cl)C=C1 CEJKAKCQVUWNNA-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 241000282414 Homo sapiens Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 229960000443 hydrochloric acid Drugs 0.000 description 1
- 235000011167 hydrochloric acid Nutrition 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000002741 palatine tonsil Anatomy 0.000 description 1
- WCZVUZYEOJQHNJ-UHFFFAOYSA-M potassium;pyridine-3-carboxylate Chemical class [K+].[O-]C(=O)C1=CC=CN=C1 WCZVUZYEOJQHNJ-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 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
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3877874A GB1442474A (en) | 1974-09-05 | 1974-09-05 | Process for the production of beta-2-p-chlorophenoxy-isobutyryloxy -ethyl nicotinate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1054153A true CA1054153A (en) | 1979-05-08 |
Family
ID=10405641
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA234,142A Expired CA1054153A (en) | 1974-09-05 | 1975-08-25 | PROCESS FOR THE PRODUCTION OF .alpha.(-2-(P-CHLOROPHENOXY)-ISOBUTYRYL)-.beta.-NICOTINOYL GLYCOL ESTER |
Country Status (17)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4375545A (en) * | 1981-06-22 | 1983-03-01 | Westwood Pharmaceuticals, Inc. | Process for the synthesis of the nicotinyl ester of 6-aminonicotinic acid |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2304405A1 (de) * | 1972-03-08 | 1973-09-13 | Hurka Wilhelm | Ester der p-chlorphenoxyisobuttersaeure und verfahren zu deren herstellung |
-
1974
- 1974-09-05 GB GB3877874A patent/GB1442474A/en not_active Expired
-
1975
- 1975-01-01 AR AR260267A patent/AR205658A1/es active
- 1975-07-12 DE DE19752531254 patent/DE2531254A1/de not_active Withdrawn
- 1975-07-18 FI FI752079A patent/FI60392C/fi not_active IP Right Cessation
- 1975-07-28 YU YU1923/75A patent/YU37132B/xx unknown
- 1975-07-30 AT AT591475A patent/AT344173B/de not_active IP Right Cessation
- 1975-08-06 NO NO752762A patent/NO752762L/no unknown
- 1975-08-21 BE BE159356A patent/BE832618R/xx active
- 1975-08-25 CA CA234,142A patent/CA1054153A/en not_active Expired
- 1975-08-29 DK DK390875A patent/DK145929C/da not_active IP Right Cessation
- 1975-08-30 JP JP50105573A patent/JPS597702B2/ja not_active Expired
- 1975-09-04 ES ES440711A patent/ES440711A1/es not_active Expired
- 1975-09-04 HU HUME1893A patent/HU169891B/hu not_active IP Right Cessation
- 1975-09-05 CH CH1151575A patent/CH584198A5/xx not_active IP Right Cessation
- 1975-09-05 PL PL1975183136A patent/PL97697B1/pl unknown
- 1975-09-05 FR FR7527367A patent/FR2283892A2/fr active Granted
- 1975-09-05 NL NL7510526A patent/NL7510526A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK390875A (da) | 1976-03-06 |
| NL7510526A (nl) | 1976-03-09 |
| PL97697B1 (pl) | 1978-03-30 |
| DK145929C (da) | 1983-09-26 |
| ES440711A1 (es) | 1977-03-16 |
| FI60392C (fi) | 1982-01-11 |
| FR2283892A2 (fr) | 1976-04-02 |
| GB1442474A (en) | 1976-07-14 |
| FI752079A7 (enrdf_load_stackoverflow) | 1976-03-06 |
| ATA591475A (de) | 1977-11-15 |
| YU192375A (en) | 1983-04-27 |
| DK145929B (da) | 1983-04-18 |
| HU169891B (enrdf_load_stackoverflow) | 1977-02-28 |
| JPS5168572A (en) | 1976-06-14 |
| AR205658A1 (es) | 1976-05-21 |
| NO752762L (enrdf_load_stackoverflow) | 1976-03-08 |
| JPS597702B2 (ja) | 1984-02-20 |
| FI60392B (fi) | 1981-09-30 |
| YU37132B (en) | 1984-08-31 |
| AT344173B (de) | 1978-07-10 |
| FR2283892B2 (enrdf_load_stackoverflow) | 1980-08-08 |
| DE2531254A1 (de) | 1976-03-25 |
| CH584198A5 (enrdf_load_stackoverflow) | 1977-01-31 |
| BE832618R (fr) | 1975-12-16 |
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