DE2654951A1 - Gemischt veresterte polyole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel - Google Patents
Gemischt veresterte polyole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittelInfo
- Publication number
- DE2654951A1 DE2654951A1 DE19762654951 DE2654951A DE2654951A1 DE 2654951 A1 DE2654951 A1 DE 2654951A1 DE 19762654951 DE19762654951 DE 19762654951 DE 2654951 A DE2654951 A DE 2654951A DE 2654951 A1 DE2654951 A1 DE 2654951A1
- Authority
- DE
- Germany
- Prior art keywords
- clof
- acid
- acyl
- compound
- sal
- 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.)
- Withdrawn
Links
- 150000001875 compounds Chemical class 0.000 title claims description 52
- 238000000034 method Methods 0.000 title claims description 37
- 229920005862 polyol Polymers 0.000 title claims description 27
- 150000003077 polyols Chemical class 0.000 title claims description 25
- 238000004519 manufacturing process Methods 0.000 title description 4
- 229940126601 medicinal product Drugs 0.000 title description 3
- -1 2-p-chlorophenoxy-2-methylpropionyl group Chemical group 0.000 claims description 52
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 229910052783 alkali metal Inorganic materials 0.000 claims description 9
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 6
- CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical group O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 claims description 6
- 229960000367 inositol Drugs 0.000 claims description 6
- 230000002829 reductive effect Effects 0.000 claims description 5
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 claims description 5
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000011664 nicotinic acid Substances 0.000 claims description 2
- 229960003512 nicotinic acid Drugs 0.000 claims description 2
- 235000001968 nicotinic acid Nutrition 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 6
- 150000001735 carboxylic acids Chemical class 0.000 claims 3
- IIRVGTWONXBBAW-UHFFFAOYSA-M disodium;dioxido(oxo)phosphanium Chemical compound [Na+].[Na+].[O-][P+]([O-])=O IIRVGTWONXBBAW-UHFFFAOYSA-M 0.000 claims 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 150000003460 sulfonic acids Polymers 0.000 claims 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 230000010933 acylation Effects 0.000 claims 1
- 238000005917 acylation reaction Methods 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 150000001450 anions Chemical class 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002924 oxiranes Chemical class 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 52
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 38
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 34
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 22
- 238000002329 infrared spectrum Methods 0.000 description 21
- 235000017557 sodium bicarbonate Nutrition 0.000 description 17
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 17
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
- 239000000460 chlorine Substances 0.000 description 14
- 239000003921 oil Substances 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 238000003756 stirring Methods 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 210000004369 blood Anatomy 0.000 description 8
- 239000008280 blood Substances 0.000 description 8
- 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 8
- TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 6
- DSGKWFGEUBCEIE-UHFFFAOYSA-N (2-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C(Cl)=O DSGKWFGEUBCEIE-UHFFFAOYSA-N 0.000 description 5
- 229960001214 clofibrate Drugs 0.000 description 5
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 229960001138 acetylsalicylic acid Drugs 0.000 description 4
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 229940051269 1,3-dichloro-2-propanol Drugs 0.000 description 3
- DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- JLWKPDBTSOFSTR-UHFFFAOYSA-N [3-[2-(4-chlorophenoxy)-2-methylpropanoyl]oxy-2-hydroxypropyl] 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound C=1C=C(Cl)C=CC=1OC(C)(C)C(=O)OCC(O)COC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 JLWKPDBTSOFSTR-UHFFFAOYSA-N 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000007795 chemical reaction product 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
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229960003750 ethyl chloride Drugs 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229960004889 salicylic acid Drugs 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XVULGGBRRNJCGL-UHFFFAOYSA-N 2-[(2-acetyloxyphenyl)methoxy]ethyl 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound CC(=O)OC1=CC=CC=C1COCCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 XVULGGBRRNJCGL-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- DCSUSQDUTXEIIH-UHFFFAOYSA-N [2-(oxiran-2-ylmethoxymethyl)phenyl] acetate Chemical compound C(C)(=O)OC=1C(COCC2CO2)=CC=CC1 DCSUSQDUTXEIIH-UHFFFAOYSA-N 0.000 description 2
- DIVBBUKIOUKDKZ-UHFFFAOYSA-N [2-[(2-acetyloxyphenyl)methoxy]-3-[2-(4-chlorophenoxy)-2-methylpropanoyl]oxypropyl] 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound CC(=O)OC1=CC=CC=C1COC(COC(=O)C(C)(C)OC=1C=CC(Cl)=CC=1)COC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 DIVBBUKIOUKDKZ-UHFFFAOYSA-N 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 238000005054 agglomeration Methods 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 210000001772 blood platelet Anatomy 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- YHRUOJUYPBUZOS-UHFFFAOYSA-N 1,3-dichloropropane Chemical compound ClCCCCl YHRUOJUYPBUZOS-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- APWQDNJPTHPAGP-UHFFFAOYSA-N 1-[(2-acetyloxyphenyl)methoxy]-3-[2-(4-chlorophenoxy)-2-methylpropanoyl]oxy-1-hydroxypropane-2-sulfonic acid Chemical compound CC(=O)OC1=CC=CC=C1COC(O)C(S(O)(=O)=O)COC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 APWQDNJPTHPAGP-UHFFFAOYSA-N 0.000 description 1
- XZQAAHHYJTZCPV-UHFFFAOYSA-N 2-(1,3-dichloropropan-2-yloxymethyl)phenol Chemical compound OC1=CC=CC=C1COC(CCl)CCl XZQAAHHYJTZCPV-UHFFFAOYSA-N 0.000 description 1
- IHGRUNBJGIGMQE-UHFFFAOYSA-N 2-(2-chloroethoxymethyl)phenol Chemical compound OC1=CC=CC=C1COCCCl IHGRUNBJGIGMQE-UHFFFAOYSA-N 0.000 description 1
- OODRWLGKUBMFLZ-UHFFFAOYSA-N 2-(4-chlorophenoxy)-2-methylpropanoyl chloride Chemical compound ClC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 OODRWLGKUBMFLZ-UHFFFAOYSA-N 0.000 description 1
- OHMWXVQPUYRIQM-UHFFFAOYSA-N 2-[(2-hydroxyphenyl)methoxy]ethyl 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound C=1C=CC=C(O)C=1COCCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 OHMWXVQPUYRIQM-UHFFFAOYSA-N 0.000 description 1
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 description 1
- IUAXUYMFMHJWHL-UHFFFAOYSA-N 2-chloroethyl 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound ClCCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 IUAXUYMFMHJWHL-UHFFFAOYSA-N 0.000 description 1
- RFEZILPHQJCCMV-UHFFFAOYSA-N 2-hydroxyethyl 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound OCCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 RFEZILPHQJCCMV-UHFFFAOYSA-N 0.000 description 1
- ILPUOPPYSQEBNJ-UHFFFAOYSA-N 2-methyl-2-phenoxypropanoic acid Chemical compound OC(=O)C(C)(C)OC1=CC=CC=C1 ILPUOPPYSQEBNJ-UHFFFAOYSA-N 0.000 description 1
- JTYLHQDHIAWRJI-UHFFFAOYSA-N 3-(4-chlorophenoxy)-2-methylpropanoyl chloride Chemical compound ClC(=O)C(C)COC1=CC=C(Cl)C=C1 JTYLHQDHIAWRJI-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- QDEOLQXBVGPPDR-UHFFFAOYSA-N 6-acetyl-6-hydroxycyclohexa-2,4-diene-1-carbonyl chloride Chemical compound CC(=O)C1(O)C=CC=CC1C(Cl)=O QDEOLQXBVGPPDR-UHFFFAOYSA-N 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- ZAFUHRHAMNSDHZ-UHFFFAOYSA-N C(C)(=O)OC=1C(COCCC)=CC=CC=1 Chemical compound C(C)(=O)OC=1C(COCCC)=CC=CC=1 ZAFUHRHAMNSDHZ-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- ZACICIWAPBDNJM-UHFFFAOYSA-N [2-(1,3-dihydroxypropan-2-ylperoxymethyl)phenyl] acetate Chemical compound CC(=O)OC1=CC=CC=C1COOC(CO)CO ZACICIWAPBDNJM-UHFFFAOYSA-N 0.000 description 1
- VVRFXEYVUZOYTI-UHFFFAOYSA-N [2-(4-chlorophenoxy)-2-methylpropanoyl] 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound C=1C=C(Cl)C=CC=1OC(C)(C)C(=O)OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 VVRFXEYVUZOYTI-UHFFFAOYSA-N 0.000 description 1
- XDRKOVCXNVIRNW-UHFFFAOYSA-N [2-[(2-acetyloxyphenyl)methoxy]-3-[3-(4-chlorophenoxy)-2-methylpropanoyl]oxypropyl] 3-(4-chlorophenoxy)-2-methylpropanoate Chemical compound C=1C=C(Cl)C=CC=1OCC(C)C(=O)OCC(OCC=1C(=CC=CC=1)OC(C)=O)COC(=O)C(C)COC1=CC=C(Cl)C=C1 XDRKOVCXNVIRNW-UHFFFAOYSA-N 0.000 description 1
- YPGCTENMFKFBGI-UHFFFAOYSA-N [2-[2-(4-chlorophenoxy)-2-methylpropanoyl]oxy-3-[(2-hydroxyphenyl)methoxy]propyl] 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound C=1C=CC=C(O)C=1COCC(OC(=O)C(C)(C)OC=1C=CC(Cl)=CC=1)COC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 YPGCTENMFKFBGI-UHFFFAOYSA-N 0.000 description 1
- GQPZJPPOGINKNT-UHFFFAOYSA-N [2-acetyloxy-3-[(2-acetyloxyphenyl)methoxy]propyl] 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound C=1C=C(Cl)C=CC=1OC(C)(C)C(=O)OCC(OC(=O)C)COCC1=CC=CC=C1OC(C)=O GQPZJPPOGINKNT-UHFFFAOYSA-N 0.000 description 1
- ACMNZPDBACFBJW-UHFFFAOYSA-N [3-[(2-acetyloxyphenyl)methoxy]-2-[2-(4-chlorophenoxy)-2-methylpropanoyl]oxypropyl] 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound CC(=O)OC1=CC=CC=C1COCC(OC(=O)C(C)(C)OC=1C=CC(Cl)=CC=1)COC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 ACMNZPDBACFBJW-UHFFFAOYSA-N 0.000 description 1
- QMLVUTCNAFPIOP-UHFFFAOYSA-N [3-[(2-acetyloxyphenyl)methoxy]-2-hydroxypropyl] 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound CC(=O)OC1=CC=CC=C1COCC(O)COC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 QMLVUTCNAFPIOP-UHFFFAOYSA-N 0.000 description 1
- WRFWWUGUCOOGED-UHFFFAOYSA-N [3-chloro-2-[3-(4-chlorophenoxy)-2-methylpropanoyl]oxypropyl] 3-(4-chlorophenoxy)-2-methylpropanoate Chemical compound C=1C=C(Cl)C=CC=1OCC(C)C(=O)OC(CCl)COC(=O)C(C)COC1=CC=C(Cl)C=C1 WRFWWUGUCOOGED-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 208000014797 chronic intestinal pseudoobstruction Diseases 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 150000005690 diesters Chemical class 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 201000005577 familial hyperlipidemia Diseases 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000009533 lab test Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- IUICKCNUBIKWJG-UHFFFAOYSA-N oxiran-2-ylmethyl 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound C1OC1COC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 IUICKCNUBIKWJG-UHFFFAOYSA-N 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- ZNCXUFVDFVBRDO-UHFFFAOYSA-N pyridine;sulfuric acid Chemical compound [H+].[O-]S([O-])(=O)=O.C1=CC=[NH+]C=C1 ZNCXUFVDFVBRDO-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229940058287 salicylic acid derivative anticestodals Drugs 0.000 description 1
- 150000003872 salicylic acid derivatives Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C305/00—Esters of sulfuric acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/16—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by esterified hydroxyl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH17376A CH616911A5 (cg-RX-API-DMAC7.html) | 1976-01-08 | 1976-01-08 | |
| CH979076A CH617175A5 (en) | 1976-07-30 | 1976-07-30 | Processes for the preparation of mixed polyol esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2654951A1 true DE2654951A1 (de) | 1977-07-21 |
Family
ID=25683750
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762654951 Withdrawn DE2654951A1 (de) | 1976-01-08 | 1976-12-03 | Gemischt veresterte polyole, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5285139A (cg-RX-API-DMAC7.html) |
| BG (1) | BG27537A3 (cg-RX-API-DMAC7.html) |
| CA (1) | CA1075708A (cg-RX-API-DMAC7.html) |
| DD (1) | DD128400A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE2654951A1 (cg-RX-API-DMAC7.html) |
| EG (1) | EG12290A (cg-RX-API-DMAC7.html) |
| ES (1) | ES453795A1 (cg-RX-API-DMAC7.html) |
| FI (1) | FI763529A7 (cg-RX-API-DMAC7.html) |
| FR (1) | FR2337552A1 (cg-RX-API-DMAC7.html) |
| GB (1) | GB1572035A (cg-RX-API-DMAC7.html) |
| GR (1) | GR61818B (cg-RX-API-DMAC7.html) |
| IL (1) | IL51039A0 (cg-RX-API-DMAC7.html) |
| NL (1) | NL7613457A (cg-RX-API-DMAC7.html) |
| PL (1) | PL117246B1 (cg-RX-API-DMAC7.html) |
| PT (1) | PT65894B (cg-RX-API-DMAC7.html) |
| RO (1) | RO70355A (cg-RX-API-DMAC7.html) |
| SE (1) | SE7613426L (cg-RX-API-DMAC7.html) |
| YU (1) | YU286476A (cg-RX-API-DMAC7.html) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL176551C (nl) * | 1979-04-25 | 1985-05-01 | Shell Int Research | Werkwijze voor de bereiding van een aromatisch koolwaterstofmengsel door katalytische omzetting van een mengsel van koolmonoxyde en waterstof. |
-
1976
- 1976-11-19 FR FR7634925A patent/FR2337552A1/fr active Pending
- 1976-11-20 GR GR52230A patent/GR61818B/el unknown
- 1976-11-24 YU YU02864/76A patent/YU286476A/xx unknown
- 1976-11-26 PT PT65894A patent/PT65894B/pt unknown
- 1976-11-26 RO RO7688569A patent/RO70355A/ro unknown
- 1976-11-30 SE SE7613426A patent/SE7613426L/xx not_active Application Discontinuation
- 1976-11-30 GB GB49963/76A patent/GB1572035A/en not_active Expired
- 1976-11-30 ES ES453795A patent/ES453795A1/es not_active Expired
- 1976-12-02 IL IL51039A patent/IL51039A0/xx unknown
- 1976-12-02 NL NL7613457A patent/NL7613457A/xx not_active Application Discontinuation
- 1976-12-02 CA CA267,026A patent/CA1075708A/en not_active Expired
- 1976-12-03 DE DE19762654951 patent/DE2654951A1/de not_active Withdrawn
- 1976-12-08 FI FI763529A patent/FI763529A7/fi not_active Application Discontinuation
- 1976-12-09 BG BG034871A patent/BG27537A3/xx unknown
- 1976-12-21 EG EG784/76A patent/EG12290A/xx active
- 1976-12-22 JP JP15351976A patent/JPS5285139A/ja active Pending
- 1976-12-27 DD DD7600196638A patent/DD128400A5/xx unknown
- 1976-12-30 PL PL1976194851A patent/PL117246B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RO70355A (ro) | 1981-08-17 |
| FR2337552A1 (fr) | 1977-08-05 |
| SE7613426L (sv) | 1977-07-09 |
| DD128400A5 (de) | 1977-11-16 |
| JPS5285139A (en) | 1977-07-15 |
| FI763529A7 (cg-RX-API-DMAC7.html) | 1977-07-09 |
| EG12290A (en) | 1979-06-30 |
| NL7613457A (nl) | 1977-07-12 |
| CA1075708A (en) | 1980-04-15 |
| PL117246B1 (en) | 1981-07-31 |
| PT65894A (fr) | 1976-12-01 |
| PL194851A1 (pl) | 1979-05-07 |
| ES453795A1 (es) | 1978-01-16 |
| PT65894B (fr) | 1978-05-18 |
| YU286476A (en) | 1982-08-31 |
| GB1572035A (en) | 1980-07-23 |
| IL51039A0 (en) | 1977-02-28 |
| BG27537A3 (bg) | 1979-11-12 |
| GR61818B (en) | 1979-01-22 |
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| 8139 | Disposal/non-payment of the annual fee |