CA1114383A - 2,6-pyridinedimethanol 2-¬a-(p-chlorophenoxy)- isobutyric acid| - Google Patents
2,6-pyridinedimethanol 2-¬a-(p-chlorophenoxy)- isobutyric acid|Info
- Publication number
- CA1114383A CA1114383A CA318,930A CA318930A CA1114383A CA 1114383 A CA1114383 A CA 1114383A CA 318930 A CA318930 A CA 318930A CA 1114383 A CA1114383 A CA 1114383A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- chlorophenoxy
- pyridinedimethanol
- ester
- isobutyric
- 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
- WWFMINHWJYHXHF-UHFFFAOYSA-N [6-(hydroxymethyl)pyridin-2-yl]methanol Chemical compound OCC1=CC=CC(CO)=N1 WWFMINHWJYHXHF-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000002148 esters Chemical class 0.000 claims abstract description 7
- 239000003377 acid catalyst Substances 0.000 claims abstract description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 235000011149 sulphuric acid Nutrition 0.000 claims abstract description 4
- 239000001117 sulphuric acid Substances 0.000 claims abstract description 3
- TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 238000005886 esterification reaction Methods 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 3
- LYWNNXMNOSKLHY-UHFFFAOYSA-N 4-hydroxy-2-methyl-5-propan-2-ylbenzenesulfonic acid Chemical compound CC(C)C1=CC(S(O)(=O)=O)=C(C)C=C1O LYWNNXMNOSKLHY-UHFFFAOYSA-N 0.000 claims 1
- 230000032050 esterification Effects 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 125000005489 p-toluenesulfonic acid group Chemical group 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 12
- 239000002253 acid Substances 0.000 abstract description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 3
- 230000004060 metabolic process Effects 0.000 abstract description 3
- -1 preferably Substances 0.000 abstract description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 abstract description 2
- 239000008096 xylene Substances 0.000 abstract description 2
- 208000035475 disorder Diseases 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 11
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 9
- 229960001214 clofibrate Drugs 0.000 description 9
- YEKQSSHBERGOJK-UHFFFAOYSA-N Pyricarbate Chemical compound CNC(=O)OCC1=CC=CC(COC(=O)NC)=N1 YEKQSSHBERGOJK-UHFFFAOYSA-N 0.000 description 8
- 229940070851 pyridinolcarbamate Drugs 0.000 description 8
- 150000002632 lipids Chemical class 0.000 description 7
- 241000700159 Rattus Species 0.000 description 6
- 235000012000 cholesterol Nutrition 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- YJBIJSVYPHRVCI-UHFFFAOYSA-N pirifibrate Chemical compound C=1C=CC(CO)=NC=1COC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 YJBIJSVYPHRVCI-UHFFFAOYSA-N 0.000 description 4
- 229950000957 pirifibrate Drugs 0.000 description 4
- 238000012453 sprague-dawley rat model Methods 0.000 description 4
- 150000003626 triacylglycerols Chemical class 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- RSMSFENOAKAUJU-UHFFFAOYSA-L bis[[2-(4-chlorophenoxy)-2-methylpropanoyl]oxy]aluminum;hydrate Chemical compound O.C=1C=C(Cl)C=CC=1OC(C)(C)C(=O)O[Al]OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 RSMSFENOAKAUJU-UHFFFAOYSA-L 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 208000031226 Hyperlipidaemia Diseases 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000260 hypercholesteremic effect Effects 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 210000000936 intestine Anatomy 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000000203 mixture 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
- 230000009467 reduction Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- IUKSYUOJRHDWRR-UHFFFAOYSA-N 2-diazonio-4,6-dinitrophenolate Chemical compound [O-]C1=C([N+]#N)C=C([N+]([O-])=O)C=C1[N+]([O-])=O IUKSYUOJRHDWRR-UHFFFAOYSA-N 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 208000012895 Gastric disease Diseases 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 206010020961 Hypocholesterolaemia Diseases 0.000 description 1
- 102000004895 Lipoproteins Human genes 0.000 description 1
- 108090001030 Lipoproteins Proteins 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 241000786363 Rhampholeon spectrum Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 206010048215 Xanthomatosis Diseases 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000004075 alteration Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 231100000132 chronic toxicity testing Toxicity 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 208000020346 hyperlipoproteinemia Diseases 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000031891 intestinal absorption Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005303 weighing 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Medicinal Preparation (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES465758A ES465758A1 (es) | 1978-01-04 | 1978-01-04 | Procedimiento de obtencion del monoester del acido p-cloro- fenoxi-isobutirico con 2,6-piridindimetanol, nuevo farmaco con accion hipocolesteremiante. |
| ES465,758 | 1978-01-04 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1114383A true CA1114383A (en) | 1981-12-15 |
Family
ID=8475233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA318,930A Expired CA1114383A (en) | 1978-01-04 | 1979-01-02 | 2,6-pyridinedimethanol 2-¬a-(p-chlorophenoxy)- isobutyric acid| |
Country Status (14)
| Country | Link |
|---|---|
| AT (1) | AT369360B (en, 2012) |
| BE (1) | BE873280A (en, 2012) |
| BR (1) | BR7900022A (en, 2012) |
| CA (1) | CA1114383A (en, 2012) |
| CH (1) | CH639072A5 (en, 2012) |
| DE (1) | DE2855811A1 (en, 2012) |
| ES (1) | ES465758A1 (en, 2012) |
| FR (1) | FR2414041A1 (en, 2012) |
| GR (1) | GR69617B (en, 2012) |
| IT (1) | IT1118259B (en, 2012) |
| LU (1) | LU80750A1 (en, 2012) |
| MX (1) | MX5621E (en, 2012) |
| PH (1) | PH14894A (en, 2012) |
| PT (1) | PT69024A (en, 2012) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2214511A1 (en) * | 1973-01-19 | 1974-08-19 | Perreau Louis | Suspension of increased storage stability - prepd. by freezing and then thawing of a solid in a liquid |
-
1978
- 1978-01-04 ES ES465758A patent/ES465758A1/es not_active Expired
- 1978-12-18 GR GR57923A patent/GR69617B/el unknown
- 1978-12-18 FR FR7835595A patent/FR2414041A1/fr active Granted
- 1978-12-22 DE DE19782855811 patent/DE2855811A1/de not_active Withdrawn
- 1978-12-28 PH PH21998A patent/PH14894A/en unknown
-
1979
- 1979-01-02 CA CA318,930A patent/CA1114383A/en not_active Expired
- 1979-01-02 LU LU80750A patent/LU80750A1/xx unknown
- 1979-01-03 MX MX797611U patent/MX5621E/es unknown
- 1979-01-03 BE BE2/57529A patent/BE873280A/xx not_active IP Right Cessation
- 1979-01-03 IT IT67006/79A patent/IT1118259B/it active
- 1979-01-03 CH CH2979A patent/CH639072A5/fr not_active IP Right Cessation
- 1979-01-03 BR BR7900022A patent/BR7900022A/pt unknown
- 1979-01-03 PT PT69024A patent/PT69024A/pt unknown
- 1979-01-04 AT AT0006179A patent/AT369360B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| FR2414041A1 (fr) | 1979-08-03 |
| PH14894A (en) | 1982-01-08 |
| GR69617B (en, 2012) | 1982-07-06 |
| CH639072A5 (en) | 1983-10-31 |
| BE873280A (fr) | 1979-07-03 |
| DE2855811A1 (de) | 1979-07-05 |
| BR7900022A (pt) | 1979-08-07 |
| ATA6179A (de) | 1982-05-15 |
| AT369360B (de) | 1982-12-27 |
| FR2414041B1 (en, 2012) | 1981-07-24 |
| PT69024A (fr) | 1979-02-01 |
| LU80750A1 (fr) | 1979-04-13 |
| ES465758A1 (es) | 1978-11-16 |
| IT1118259B (it) | 1986-02-24 |
| IT7967006A0 (it) | 1979-01-03 |
| MX5621E (es) | 1983-11-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69606840D1 (de) | Monohydrate von Aminobenzensulfonsäurederivaten und Verfahren zu ihrer Herstellung | |
| US20140364500A1 (en) | Ursolic acid salts for treating diabetes and obesity | |
| IE72479B1 (en) | Codeine salt of a substituted carbonacid process of its preparation its use and pharmaceutical preparations | |
| GB2038818A (en) | ???,???-Dihydropolyprenyl Alcohols and Pharmaceutical Compositions thereof | |
| CA1114383A (en) | 2,6-pyridinedimethanol 2-¬a-(p-chlorophenoxy)- isobutyric acid| | |
| KR880701235A (ko) | 디벤즈[b,e] 옥세핀유도체 및 그것을 유효성분으로 하는 의약 | |
| EP0232227B1 (en) | Phosphorylalkanolamide derivatives of l-carnitine and pharmaceutical compositions containing same | |
| GB2082173A (en) | Isopsoralens | |
| JPS5827796B2 (ja) | テオフイリニルメチルジオキソラン誘導体およびその製法 | |
| US5149688A (en) | Methods, compounds, and compositions for immunosuppression | |
| EP0228314A2 (en) | Use of ethanol/amine derivatives in treating or preventing hyperlipemia | |
| CN109503480B (zh) | 含喹啉母核的非季铵盐肟类化合物及其医药用途 | |
| DE69515498T2 (de) | Naphthyridinderivate | |
| JPS62294616A (ja) | 抗真菌用薬剤 | |
| US3433789A (en) | S-benzoyloxymethyl-thiamines | |
| FI66597C (fi) | Foerfarande foer framstaellning av en antiarrytmisk 4-hydroxi-3-metoxi-n-(2-(2-(1-metyl-2-piperidinyl)-etyl)fenyl)bensamidoch farmaceutisk godtagbara syraadditionssalter daerav | |
| KR810000382B1 (ko) | 빈카민-5-피리독살포스페이트의 제법 | |
| US4234583A (en) | 2-Chloro-4-(4-lower alkyl-1-piperazinyl)benzenemethanol, N.sup.ω -oxides and methods for their preparation | |
| US3928602A (en) | Substituted phenoxymalonic acids, esters thereof and hypolipaemic agents containing the same for lowering lipid levels | |
| AU607621B2 (en) | Novel esters of estramustine | |
| CA1270248A (en) | Imidazole compounds as immunomodulating agents | |
| JPS61204122A (ja) | 肝臓疾患治療剤 | |
| EP0198508A1 (en) | L-phosphoserine salts, a process for the preparation thereof and pharmaceutical compositions containing them | |
| IE790237L (en) | Benzimidazol-2-ones. | |
| JPH0228113A (ja) | 高尿酸血症改善・治療剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |