CH639072A5 - 2-[ alpha -(p-Chlorophenoxy)isobutyrate] of 2,6-pyridinedimethanol and process for its preparation - Google Patents
2-[ alpha -(p-Chlorophenoxy)isobutyrate] of 2,6-pyridinedimethanol and process for its preparation Download PDFInfo
- Publication number
- CH639072A5 CH639072A5 CH2979A CH2979A CH639072A5 CH 639072 A5 CH639072 A5 CH 639072A5 CH 2979 A CH2979 A CH 2979A CH 2979 A CH2979 A CH 2979A CH 639072 A5 CH639072 A5 CH 639072A5
- Authority
- CH
- Switzerland
- Prior art keywords
- pyridinedimethanol
- acid
- isobutyrate
- chlorophenoxy
- hydrochloride
- Prior art date
Links
- WWFMINHWJYHXHF-UHFFFAOYSA-N [6-(hydroxymethyl)pyridin-2-yl]methanol Chemical compound OCC1=CC=CC(CO)=N1 WWFMINHWJYHXHF-UHFFFAOYSA-N 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 7
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- -1 2- (p-chlorophenoxy) 2,6-pyridinedimethanol isobutyrate hydrochloride Chemical compound 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 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 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 230000032050 esterification Effects 0.000 claims 2
- 238000005886 esterification reaction Methods 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 230000037356 lipid metabolism Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000012429 reaction media Substances 0.000 claims 1
- 125000000542 sulfonic acid group Chemical group 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 description 23
- 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 12
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 10
- 229960001214 clofibrate Drugs 0.000 description 10
- YEKQSSHBERGOJK-UHFFFAOYSA-N Pyricarbate Chemical compound CNC(=O)OCC1=CC=CC(COC(=O)NC)=N1 YEKQSSHBERGOJK-UHFFFAOYSA-N 0.000 description 9
- 229940070851 pyridinolcarbamate Drugs 0.000 description 9
- 235000012000 cholesterol Nutrition 0.000 description 6
- 150000002632 lipids Chemical class 0.000 description 6
- 241000700159 Rattus Species 0.000 description 4
- 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 4
- 230000000052 comparative effect Effects 0.000 description 4
- 230000003247 decreasing effect Effects 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
- 241001465754 Metazoa Species 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- 238000010521 absorption reaction Methods 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
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- GEGSSUSEWOHAFE-UHFFFAOYSA-N 2-(4-chlorphenoxy)-ethanol Chemical compound OCCOC1=CC=C(Cl)C=C1 GEGSSUSEWOHAFE-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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 208000017170 Lipid metabolism disease Diseases 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000283977 Oryctolagus Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 108010062497 VLDL Lipoproteins Proteins 0.000 description 1
- 206010048215 Xanthomatosis Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000009471 action Effects 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
- 125000003118 aryl group Chemical group 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
- 230000002490 cerebral effect Effects 0.000 description 1
- 230000008859 change 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
- 231100000673 dose–response relationship Toxicity 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 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
- 244000144993 groups of animals Species 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
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 1
- 208000020346 hyperlipoproteinemia Diseases 0.000 description 1
- 208000006575 hypertriglyceridemia Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000031891 intestinal absorption Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 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
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000012047 saturated solution Substances 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
- 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)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicinal Preparation (AREA)
Applications Claiming Priority (1)
| 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. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH639072A5 true CH639072A5 (en) | 1983-10-31 |
Family
ID=8475233
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH2979A CH639072A5 (en) | 1978-01-04 | 1979-01-03 | 2-[ alpha -(p-Chlorophenoxy)isobutyrate] of 2,6-pyridinedimethanol and process for its preparation |
Country Status (14)
| Country | Link |
|---|---|
| AT (1) | AT369360B (da) |
| BE (1) | BE873280A (da) |
| BR (1) | BR7900022A (da) |
| CA (1) | CA1114383A (da) |
| CH (1) | CH639072A5 (da) |
| DE (1) | DE2855811A1 (da) |
| ES (1) | ES465758A1 (da) |
| FR (1) | FR2414041A1 (da) |
| GR (1) | GR69617B (da) |
| IT (1) | IT1118259B (da) |
| LU (1) | LU80750A1 (da) |
| MX (1) | MX5621E (da) |
| PH (1) | PH14894A (da) |
| PT (1) | PT69024A (da) |
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 LU LU80750A patent/LU80750A1/xx unknown
- 1979-01-02 CA CA318,930A patent/CA1114383A/en not_active Expired
- 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
- 1979-01-03 MX MX797611U patent/MX5621E/es unknown
- 1979-01-03 BE BE2/57529A patent/BE873280A/xx not_active IP Right Cessation
- 1979-01-04 AT AT0006179A patent/AT369360B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| BE873280A (fr) | 1979-07-03 |
| LU80750A1 (fr) | 1979-04-13 |
| DE2855811A1 (de) | 1979-07-05 |
| MX5621E (es) | 1983-11-09 |
| GR69617B (da) | 1982-07-06 |
| FR2414041B1 (da) | 1981-07-24 |
| CA1114383A (en) | 1981-12-15 |
| IT7967006A0 (it) | 1979-01-03 |
| BR7900022A (pt) | 1979-08-07 |
| FR2414041A1 (fr) | 1979-08-03 |
| PT69024A (fr) | 1979-02-01 |
| PH14894A (en) | 1982-01-08 |
| IT1118259B (it) | 1986-02-24 |
| ATA6179A (de) | 1982-05-15 |
| AT369360B (de) | 1982-12-27 |
| ES465758A1 (es) | 1978-11-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0330532B1 (fr) | Nouvelle forme galénique du fénofibrate | |
| US20070027218A1 (en) | Pharmaceutical compositions comprising higher primary alcohols and ezetimibe and process of preparation thereof | |
| WO1994015607A1 (fr) | Application de la lamotrigine dans le traitement de la maladie de parkinson et des syndromes parkinsoniens | |
| FR2663633A1 (fr) | Nouvelles chalcones, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. | |
| BE895724A (fr) | Nouvelle utilisation therapeutique de la dihydrocyclosporine d | |
| CH639072A5 (en) | 2-[ alpha -(p-Chlorophenoxy)isobutyrate] of 2,6-pyridinedimethanol and process for its preparation | |
| US4883813A (en) | Method of treating inflammation in mammals utilizing ketobutyrolactones and furylbutyrolactones | |
| JP7257091B2 (ja) | 認知症の治療及び予防薬 | |
| JPS6245525A (ja) | 脂質低下剤 | |
| CA1270762A (fr) | Compositions pharmaceutiques renfermant un derive de l'acide maleopimarique | |
| EP0006061A1 (fr) | Médicament constitué par un dérivé de cyclopentyl-aldéhyde | |
| FR2516793A1 (fr) | Nouveaux medicaments immunomodulateurs contenant un derive de trithiazolepentamethylidene-cyanine | |
| EP1007522B1 (fr) | 2- 4-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]piperazin-1-yl -5-fluoropyrimidine, sa preparation et son utilisation therapeutique | |
| JP3102908B2 (ja) | ３−フェニルプロペナール誘導体を有効成分とする抗潰瘍剤 | |
| CA2127545A1 (fr) | Nouvelle application therapeutique de derives de pyridylpyrrolothiazole carboxamide | |
| DE68907893T2 (de) | Neue 1,3,4,-thiadiazolderivate und antigeschwulstmittel, die diese enthalten. | |
| EP0412877A1 (fr) | Nouvelle forme galénique orale améliorant la biodisponibilité | |
| US20080247962A1 (en) | Pharmaceutical Compositions Comprising Higher Primary Aliphatic Alcohols and Hmg Coa Reductase Inhibitor and Process of Preparation Thereof | |
| CH628321A5 (en) | Process for the preparation of derivatives of isobutyramide and medical composition containing these derivatives | |
| FR2700114A1 (fr) | Application de la lamotrigine dans le traitement de la maladie de Parkinson et des syndromes parkinsoniens. | |
| LU83644A1 (fr) | Nouveau derive de benzanilide doue d'activite anti-arythmique son procede de preparation et composition pharmaceutique le contenant | |
| WO2003002585A1 (fr) | Derives de [4-(4-cyanobenzoyl)phenyl]glycopyranoside, utilisation en tant que medicament, procede d'obtention et compositions | |
| WO2003002586A1 (fr) | Derives de [4-(4-cyanobenzoyl)phenyl]glycofuranoside, utilisation en tant que medicament, procede d'obtention et compositions pharmaceutiques les contenant | |
| FR2573071A1 (fr) | N-(hydroxy-2-dimethyl-1,1-ethyl)-amino-2-phenyl-1-ethanol utile notamment comme anti-inflammatoire, et son procede de preparation | |
| JPH06211657A (ja) | 尿酸排泄剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |