GB1572035A - Therapeutically active glycerol ester containing clofibryl- and 2-acetylsalicylgroups - Google Patents
Therapeutically active glycerol ester containing clofibryl- and 2-acetylsalicylgroups Download PDFInfo
- Publication number
- GB1572035A GB1572035A GB49963/76A GB4996376A GB1572035A GB 1572035 A GB1572035 A GB 1572035A GB 49963/76 A GB49963/76 A GB 49963/76A GB 4996376 A GB4996376 A GB 4996376A GB 1572035 A GB1572035 A GB 1572035A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- residue
- asp
- chlorophenoxy
- 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
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 title claims description 16
- -1 glycerol ester Chemical class 0.000 title claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 30
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims description 2
- 229960004889 salicylic acid Drugs 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- 239000000243 solution Substances 0.000 description 24
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 20
- 239000000047 product Substances 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 229940093499 ethyl acetate Drugs 0.000 description 11
- 235000019439 ethyl acetate Nutrition 0.000 description 11
- 230000006870 function Effects 0.000 description 10
- 238000000034 method Methods 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- TXCGAZHTZHNUAI-UHFFFAOYSA-N clofibric acid Chemical compound OC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 TXCGAZHTZHNUAI-UHFFFAOYSA-N 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- HHLJUSLZGFYWKW-UHFFFAOYSA-N triethanolamine hydrochloride Chemical compound Cl.OCCN(CCO)CCO HHLJUSLZGFYWKW-UHFFFAOYSA-N 0.000 description 6
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- DSGKWFGEUBCEIE-UHFFFAOYSA-N (2-carbonochloridoylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C(Cl)=O DSGKWFGEUBCEIE-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 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 4
- 229960001138 acetylsalicylic acid Drugs 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 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 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
- 229960001214 clofibrate Drugs 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N dimethylmethane Natural products CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 230000000181 anti-adherent effect Effects 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 2
- 239000003315 2-(4-chlorophenoxy)-2-methylpropanoic acid Substances 0.000 description 2
- 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 2
- 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 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 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 2
- 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 2
- 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 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000002744 anti-aggregatory effect Effects 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000001772 blood platelet Anatomy 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 229950008441 clofibric acid Drugs 0.000 description 2
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000002207 metabolite Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 230000036470 plasma concentration Effects 0.000 description 2
- 230000009993 protective function Effects 0.000 description 2
- MAUQVQSXTOZPSX-UHFFFAOYSA-M sodium;2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound [Na+].[O-]C(=O)C(C)(C)OC1=CC=C(Cl)C=C1 MAUQVQSXTOZPSX-UHFFFAOYSA-M 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 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
- WOFOAEQYRWHJEQ-UHFFFAOYSA-N 3,5-dichloro-3-[(2-hydroxyphenyl)methoxy]pentan-2-one Chemical compound ClCCC(Cl)(C(=O)C)OCC1=CC=CC=C1O WOFOAEQYRWHJEQ-UHFFFAOYSA-N 0.000 description 1
- LAMUXTNQCICZQX-UHFFFAOYSA-N 3-chloropropan-1-ol Chemical compound OCCCCl LAMUXTNQCICZQX-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
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- 229910000831 Steel Inorganic materials 0.000 description 1
- 208000010513 Stupor Diseases 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
- 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 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
- XZBAKDVDVRPSCH-UHFFFAOYSA-N [3-[2-(4-chlorophenoxy)-2-methylpropanoyl]oxy-2-[(2-hydroxyphenyl)methoxy]propyl] 2-(4-chlorophenoxy)-2-methylpropanoate Chemical compound C=1C=C(Cl)C=CC=1OC(C)(C)C(=O)OCC(OCC=1C(=CC=CC=1)O)COC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 XZBAKDVDVRPSCH-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
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000011033 desalting Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002118 epoxides Chemical group 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent 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
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- PCTXBFQNMDKOSP-UHFFFAOYSA-M sodium;(2-carboxyphenyl) sulfate Chemical group [Na+].OS(=O)(=O)OC1=CC=CC=C1C([O-])=O PCTXBFQNMDKOSP-UHFFFAOYSA-M 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 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
- 238000002627 tracheal intubation Methods 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)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Obesity (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 (fr) | 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 |
|---|---|
| GB1572035A true GB1572035A (en) | 1980-07-23 |
Family
ID=25683750
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB49963/76A Expired GB1572035A (en) | 1976-01-08 | 1976-11-30 | Therapeutically active glycerol ester containing clofibryl- and 2-acetylsalicylgroups |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5285139A (fr) |
| BG (1) | BG27537A3 (fr) |
| CA (1) | CA1075708A (fr) |
| DD (1) | DD128400A5 (fr) |
| DE (1) | DE2654951A1 (fr) |
| EG (1) | EG12290A (fr) |
| ES (1) | ES453795A1 (fr) |
| FI (1) | FI763529A (fr) |
| FR (1) | FR2337552A1 (fr) |
| GB (1) | GB1572035A (fr) |
| GR (1) | GR61818B (fr) |
| IL (1) | IL51039A0 (fr) |
| NL (1) | NL7613457A (fr) |
| PL (1) | PL117246B1 (fr) |
| PT (1) | PT65894B (fr) |
| RO (1) | RO70355A (fr) |
| SE (1) | SE7613426L (fr) |
| YU (1) | YU286476A (fr) |
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/fr unknown
- 1976-11-26 RO RO7688569A patent/RO70355A/fr unknown
- 1976-11-30 GB GB49963/76A patent/GB1572035A/en not_active Expired
- 1976-11-30 SE SE7613426A patent/SE7613426L/xx not_active Application Discontinuation
- 1976-11-30 ES ES453795A patent/ES453795A1/es not_active Expired
- 1976-12-02 IL IL51039A patent/IL51039A0/xx unknown
- 1976-12-02 CA CA267,026A patent/CA1075708A/fr not_active Expired
- 1976-12-02 NL NL7613457A patent/NL7613457A/xx not_active Application Discontinuation
- 1976-12-03 DE DE19762654951 patent/DE2654951A1/de not_active Withdrawn
- 1976-12-08 FI FI763529A patent/FI763529A/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 |
|---|---|
| CA1075708A (fr) | 1980-04-15 |
| YU286476A (en) | 1982-08-31 |
| GR61818B (en) | 1979-01-22 |
| BG27537A3 (en) | 1979-11-12 |
| DE2654951A1 (de) | 1977-07-21 |
| IL51039A0 (en) | 1977-02-28 |
| PL194851A1 (pl) | 1979-05-07 |
| PT65894A (fr) | 1976-12-01 |
| RO70355A (fr) | 1981-08-17 |
| SE7613426L (sv) | 1977-07-09 |
| ES453795A1 (es) | 1978-01-16 |
| PL117246B1 (en) | 1981-07-31 |
| FI763529A (fr) | 1977-07-09 |
| NL7613457A (nl) | 1977-07-12 |
| FR2337552A1 (fr) | 1977-08-05 |
| PT65894B (fr) | 1978-05-18 |
| DD128400A5 (de) | 1977-11-16 |
| EG12290A (en) | 1979-06-30 |
| JPS5285139A (en) | 1977-07-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS59170097A (ja) | Ｏ−アシル−アルカンジオ−ル−ホスホリピドおよびその製法 | |
| JPS6081194A (ja) | ケトアルキルリン脂質 | |
| Paris et al. | Glycerides as prodrugs. 3. Synthesis and antiinflammatory activity of [1-(p-chlorobenzoyl)-5-methoxy-2-methylindole-3-acetyl] glycerides (indomethacin glycerides) | |
| WO1983003096A1 (fr) | Derives d'immidazole | |
| GB2088856A (en) | 7-substituted pg12-derivatives their preparation and pharmaceutical compositions containing them | |
| Stamatov et al. | Regioselective opening of an oxirane system with trifluoroacetic anhydride. A general method for the synthesis of 2-monoacyl-and 1, 3-symmetrical triacylglycerols | |
| GB1572035A (en) | Therapeutically active glycerol ester containing clofibryl- and 2-acetylsalicylgroups | |
| AU3159293A (en) | New BHT ether compounds and their use as hypolipidemic and antiatherosclerotic drugs | |
| US4145443A (en) | Bicyclo 3.1.0!hexylethylaminocarbonyl-substituted naphthyloxy cardiovascular agents | |
| EP0043472B1 (fr) | 3-Hydrocarbylthio-2-acyloxypropyl 2-trimethylammonioethyl phosphates, leur procédé de préparation et compositions pharmaceutiques les contenant | |
| US4118583A (en) | Mixed esters of polyols | |
| JPH0314030B2 (fr) | ||
| US4275068A (en) | Lipid lowering alkylene glycols and ester derivatives thereof | |
| JPS6123178B2 (fr) | ||
| EP0000506A2 (fr) | Ethers O- ou S- phényle substitué d'alcools cycloaliphatiques, leur procédé de préparation et leur application comme hypolipémiants; leurs esters avec des acides cyclopropanecarboxyliques et l'application de ces esters comme insecticides | |
| JPS6353968B2 (fr) | ||
| US5276180A (en) | Process for making succinyl acetone | |
| EP0481253B1 (fr) | Dérivés d'acides p-oxybenzoiques, procédés pour leur préparation et leur utilisation comme médicaments | |
| JPH053474B2 (fr) | ||
| DE19832238A1 (de) | Fluorierte Etherlipide, Verfahren zu deren Herstellung und Verwendung als Arzneimittel | |
| JPS6032763A (ja) | 新規な１１−オキソプロスタン酸誘導体ならびにその利用 | |
| EP0089857B1 (fr) | Composés pharmaceutiques et leur procédé de fabrication | |
| WO1983003411A1 (fr) | Compose pharmaceutique et son procede de fabrication | |
| Campbell et al. | The preparation and crystal structure of 2-phenoxypropenoic acid | |
| KR800001260B1 (ko) | 페닐 초산 에스테르 유도체의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |