CH517687A - Verfahren zur Herstellung von neuen Aryloxy- und Arylthioessigsäurederivaten - Google Patents
Verfahren zur Herstellung von neuen Aryloxy- und ArylthioessigsäurederivatenInfo
- Publication number
- CH517687A CH517687A CH1447671A CH1447671A CH517687A CH 517687 A CH517687 A CH 517687A CH 1447671 A CH1447671 A CH 1447671A CH 1447671 A CH1447671 A CH 1447671A CH 517687 A CH517687 A CH 517687A
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- general formula
- hexahydro
- hexahydrofluoren
- solution
- Prior art date
Links
- 125000004104 aryloxy group Chemical group 0.000 title claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 22
- -1 alkaline earth metal salts Chemical class 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 17
- 239000003513 alkali Substances 0.000 claims description 11
- 150000001735 carboxylic acids Chemical class 0.000 claims description 9
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 229910002092 carbon dioxide Inorganic materials 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000001569 carbon dioxide Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 230000000055 hyoplipidemic effect Effects 0.000 abstract description 3
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract description 2
- 238000010561 standard procedure Methods 0.000 abstract description 2
- 150000001408 amides Chemical class 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YENHPUBUIQVFPK-UHFFFAOYSA-N 2-(5,6,7,8,8a,9-hexahydro-4bH-fluoren-2-yloxy)heptanoic acid Chemical compound C1=C(C=CC=2C3CCCCC3CC12)OC(C(=O)O)CCCCC YENHPUBUIQVFPK-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000002775 capsule Substances 0.000 description 8
- 229920000159 gelatin Polymers 0.000 description 7
- 235000019322 gelatine Nutrition 0.000 description 7
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- 108010010803 Gelatin Proteins 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 239000008273 gelatin Substances 0.000 description 6
- 235000011852 gelatine desserts Nutrition 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000454 talc Substances 0.000 description 6
- 229910052623 talc Inorganic materials 0.000 description 6
- XOGLRDCCKJUTKO-UHFFFAOYSA-N 2-(5,6,7,8,8a,9-hexahydro-4bH-fluoren-2-ylsulfanyl)heptanoic acid Chemical compound C1=C(C=CC=2C3CCCCC3CC12)SC(C(=O)O)CCCCC XOGLRDCCKJUTKO-UHFFFAOYSA-N 0.000 description 5
- NSCCCRCGJBJLOR-UHFFFAOYSA-N 5,6,7,8,8a,9-hexahydro-4bh-fluoren-2-ol Chemical compound C1CCCC2CC3=CC(O)=CC=C3C21 NSCCCRCGJBJLOR-UHFFFAOYSA-N 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000008120 corn starch Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000829 suppository Substances 0.000 description 5
- OSJFWOVKJZKBOA-UHFFFAOYSA-N 2,3,4,4a,9,9a-hexahydro-1h-fluorene Chemical compound C12=CC=CC=C2CC2C1CCCC2 OSJFWOVKJZKBOA-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 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 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 230000007717 exclusion Effects 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 159000000007 calcium salts Chemical class 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 239000012259 ether extract Substances 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920001592 potato starch Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 235000012239 silicon dioxide Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- KFTYDTJYPQAGHY-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methyl]cyclohexan-1-one Chemical compound COC1=CC=CC(CC2C(CCCC2)=O)=C1 KFTYDTJYPQAGHY-UHFFFAOYSA-N 0.000 description 2
- OOSNWUQTBWDRSA-UHFFFAOYSA-N 2-[(3-methoxyphenyl)methylidene]cyclohexan-1-one Chemical compound COC1=CC=CC(C=C2C(CCCC2)=O)=C1 OOSNWUQTBWDRSA-UHFFFAOYSA-N 0.000 description 2
- DAEHKEAOGPULJI-UHFFFAOYSA-N 5,6,7,8,8a,9-hexahydro-4bH-fluorene-2-sulfonyl chloride Chemical compound C1=C(C=CC=2C3CCCCC3CC12)S(=O)(=O)Cl DAEHKEAOGPULJI-UHFFFAOYSA-N 0.000 description 2
- QXIPTDHEVKPAMV-UHFFFAOYSA-N 5,6,7,8,8a,9-hexahydro-4bH-fluorene-2-thiol Chemical compound C1=C(C=CC=2C3CCCCC3CC12)S QXIPTDHEVKPAMV-UHFFFAOYSA-N 0.000 description 2
- KWNQDPATGIWMJM-UHFFFAOYSA-N 7-methoxy-2,3,4,4a,9,9a-hexahydro-1h-fluorene Chemical compound C1CCCC2CC3=CC(OC)=CC=C3C21 KWNQDPATGIWMJM-UHFFFAOYSA-N 0.000 description 2
- IAOHSPBWEKHGSV-UHFFFAOYSA-N 7-methoxy-2,3,4,9-tetrahydro-1h-fluorene Chemical compound C1CCCC2=C1CC1=CC(OC)=CC=C12 IAOHSPBWEKHGSV-UHFFFAOYSA-N 0.000 description 2
- 244000215068 Acacia senegal Species 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- BOLMSJNOWYBERZ-UHFFFAOYSA-N C(C)OC(C(C(=O)OCC)(CCCCC)SC1=CC=2CC3CCCCC3C2C=C1)=O Chemical compound C(C)OC(C(C(=O)OCC)(CCCCC)SC1=CC=2CC3CCCCC3C2C=C1)=O BOLMSJNOWYBERZ-UHFFFAOYSA-N 0.000 description 2
- QDYRJSQAFAEAMF-UHFFFAOYSA-N CCOC(C(COC1=CC(CC2C3CCCC2)=C3C=C1)C(O)=O)=O Chemical compound CCOC(C(COC1=CC(CC2C3CCCC2)=C3C=C1)C(O)=O)=O QDYRJSQAFAEAMF-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920000084 Gum arabic Polymers 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000000205 acacia gum Substances 0.000 description 2
- 235000010489 acacia gum Nutrition 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- PSOUETBRCHLRNY-UHFFFAOYSA-N diethyl 2-bromo-2-pentylpropanedioate Chemical compound CCCCCC(Br)(C(=O)OCC)C(=O)OCC PSOUETBRCHLRNY-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002511 suppository base Substances 0.000 description 2
- 231100001274 therapeutic index Toxicity 0.000 description 2
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 2
- JEBCWDNUQFZVOM-UHFFFAOYSA-N 2-(5,6,7,8,8a,9-hexahydro-4bH-fluoren-2-yloxy)-2-pentylpropanedioic acid Chemical compound C1=C(C=CC=2C3CCCCC3CC12)OC(C(=O)O)(C(=O)O)CCCCC JEBCWDNUQFZVOM-UHFFFAOYSA-N 0.000 description 1
- OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 1
- VGUWZCUCNQXGBU-UHFFFAOYSA-N 3-[(4-methylpiperazin-1-yl)methyl]-5-nitro-1h-indole Chemical compound C1CN(C)CCN1CC1=CNC2=CC=C([N+]([O-])=O)C=C12 VGUWZCUCNQXGBU-UHFFFAOYSA-N 0.000 description 1
- XGFXOPUNRYZUBB-UHFFFAOYSA-N 5,6,7,8,8a,9-hexahydro-4bH-fluorene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=C2C3CCCCC3CC2=C1 XGFXOPUNRYZUBB-UHFFFAOYSA-N 0.000 description 1
- OOCRPNTZVSMEIJ-UHFFFAOYSA-N 9h-fluorene-2-sulfonyl chloride Chemical compound C1=CC=C2C3=CC=C(S(=O)(=O)Cl)C=C3CC2=C1 OOCRPNTZVSMEIJ-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 229920000945 Amylopectin Polymers 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- LDNBQEKWAQTARO-UHFFFAOYSA-N C(C)OC(C(C(=O)OCC)(CCCCC)OC1=CC=2CC3CCCCC3C2C=C1)=O Chemical compound C(C)OC(C(C(=O)OCC)(CCCCC)OC1=CC=2CC3CCCCC3C2C=C1)=O LDNBQEKWAQTARO-UHFFFAOYSA-N 0.000 description 1
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- 241000207199 Citrus Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 241001466453 Laminaria Species 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 241000530268 Lycaena heteronea Species 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- ZJTGSKFZBBCQBW-UHFFFAOYSA-N acetaldehyde;lead Chemical compound [Pb].CC=O ZJTGSKFZBBCQBW-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- ZJWSPHOYDIRACO-UHFFFAOYSA-N diethyl 2-(5,6,7,8,8a,9-hexahydro-4bH-fluoren-2-yloxy)-2-decylpropanedioate Chemical compound C(C)OC(C(C(=O)OCC)(CCCCCCCCCC)OC1=CC=2CC3CCCCC3C2C=C1)=O ZJWSPHOYDIRACO-UHFFFAOYSA-N 0.000 description 1
- FNJVDWXUKLTFFL-UHFFFAOYSA-N diethyl 2-bromopropanedioate Chemical group CCOC(=O)C(Br)C(=O)OCC FNJVDWXUKLTFFL-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003791 organic solvent mixture Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/72—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/06—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members
- C07C2603/10—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings
- C07C2603/12—Ortho- or ortho- and peri-condensed systems containing three rings containing at least one ring with less than six ring members containing five-membered rings only one five-membered ring
- C07C2603/18—Fluorenes; Hydrogenated fluorenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1447671A CH517687A (de) | 1969-07-09 | 1969-07-09 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioessigsäurederivaten |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1447671A CH517687A (de) | 1969-07-09 | 1969-07-09 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioessigsäurederivaten |
| CH1045669A CH517064A (de) | 1969-07-09 | 1969-07-09 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioessigsäurederivaten |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH517687A true CH517687A (de) | 1972-01-15 |
Family
ID=4363417
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1447671A CH517687A (de) | 1969-07-09 | 1969-07-09 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioessigsäurederivaten |
| CH1447571A CH517067A (de) | 1969-07-09 | 1969-07-09 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioessigsäuren |
| CH1447971A CH517068A (de) | 1969-07-09 | 1969-07-09 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioessigsäurederivaten |
| CH1447471A CH517066A (de) | 1969-07-09 | 1969-07-09 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioessigsäuren und ihren Alkali- und Erdalkalimetallsalzen |
| CH1045669A CH517064A (de) | 1969-07-09 | 1969-07-09 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioessigsäurederivaten |
| CH1447771A CH517688A (de) | 1969-07-09 | 1969-07-09 | Verfahren zur Herstellung von neuen Aryloxy-essigsäurederivaten |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1447571A CH517067A (de) | 1969-07-09 | 1969-07-09 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioessigsäuren |
| CH1447971A CH517068A (de) | 1969-07-09 | 1969-07-09 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioessigsäurederivaten |
| CH1447471A CH517066A (de) | 1969-07-09 | 1969-07-09 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioessigsäuren und ihren Alkali- und Erdalkalimetallsalzen |
| CH1045669A CH517064A (de) | 1969-07-09 | 1969-07-09 | Verfahren zur Herstellung von neuen Aryloxy- und Arylthioessigsäurederivaten |
| CH1447771A CH517688A (de) | 1969-07-09 | 1969-07-09 | Verfahren zur Herstellung von neuen Aryloxy-essigsäurederivaten |
Country Status (12)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3976686A (en) * | 1972-10-13 | 1976-08-24 | Merck & Co., Inc. | [1-Oxo-2,3-hydrocarbylene-5-indanyloxy(or thio)]alkanoic acids |
| US4172211A (en) * | 1978-03-31 | 1979-10-23 | Chevron Research Company | Process for preparing thioethers of mercapto-acids |
| WO2000006560A1 (en) | 1998-07-30 | 2000-02-10 | Warner-Lambert Company | Tricyclic heteroaromatics and their derivatives as inhibitors of matrix metalloproteinases |
| EP1100792B1 (en) | 1998-07-30 | 2004-03-17 | Warner-Lambert Company LLC | Tricyclic sulfonamides and their derivatives as inhibitors of matrix metalloproteinases |
| KR101547573B1 (ko) * | 2007-03-09 | 2015-08-26 | 사노피 | 치환된 디하이드로 및 테트라하이드로 옥사졸로피리미디논, 이의 제조방법 및 용도 |
| DE102008048580B4 (de) * | 2008-09-23 | 2014-08-21 | List Holding Ag | Vorrichtung zur Durchführung von mechanischen, chemischen und/oder thermischen Prozessen |
| AR078171A1 (es) | 2009-09-15 | 2011-10-19 | Sanofi Aventis | Dihidrobenzocicloalquiloximetil-oxazolopirimidinonas sustituidas, preparacion y uso de las mismas |
| US20230174485A1 (en) * | 2020-03-25 | 2023-06-08 | Sri International | Lipoxygenase inhibitors |
-
1969
- 1969-07-09 CH CH1447671A patent/CH517687A/de not_active IP Right Cessation
- 1969-07-09 CH CH1447571A patent/CH517067A/de not_active IP Right Cessation
- 1969-07-09 CH CH1447971A patent/CH517068A/de not_active IP Right Cessation
- 1969-07-09 CH CH1447471A patent/CH517066A/de not_active IP Right Cessation
- 1969-07-09 CH CH1045669A patent/CH517064A/de not_active IP Right Cessation
- 1969-07-09 CH CH1447771A patent/CH517688A/de not_active IP Right Cessation
-
1970
- 1970-07-02 NL NL7009808A patent/NL7009808A/xx unknown
- 1970-07-07 SU SU1454007A patent/SU370772A3/ru active
- 1970-07-08 FR FR7025300A patent/FR2059498A1/fr not_active Withdrawn
- 1970-07-08 ES ES381579A patent/ES381579A1/es not_active Expired
- 1970-07-08 ES ES381582A patent/ES381582A1/es not_active Expired
- 1970-07-08 AT AT617070A patent/AT299177B/de active
- 1970-07-08 BE BE753172D patent/BE753172A/xx unknown
- 1970-07-08 ES ES381583A patent/ES381583A1/es not_active Expired
- 1970-07-08 US US00053293A patent/US3743663A/en not_active Expired - Lifetime
- 1970-07-08 AU AU17289/70A patent/AU1728970A/en not_active Expired
- 1970-07-08 IL IL34872A patent/IL34872A0/xx unknown
- 1970-07-08 ZA ZA704720A patent/ZA704720B/xx unknown
- 1970-07-08 ES ES381581A patent/ES381581A1/es not_active Expired
- 1970-07-08 ES ES381577A patent/ES381577A1/es not_active Expired
- 1970-07-08 ES ES381580A patent/ES381580A1/es not_active Expired
- 1970-07-08 DE DE19702033959 patent/DE2033959A1/de active Pending
- 1970-07-08 ES ES381578A patent/ES381578A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IL34872A0 (en) | 1970-09-17 |
| ES381582A1 (es) | 1973-01-16 |
| CH517066A (de) | 1971-12-31 |
| BE753172A (fr) | 1971-01-08 |
| DE2033959A1 (de) | 1971-02-04 |
| ES381577A1 (es) | 1972-11-16 |
| AT299177B (de) | 1972-06-12 |
| CH517068A (de) | 1971-12-31 |
| ES381581A1 (es) | 1973-01-16 |
| ES381579A1 (es) | 1972-11-16 |
| ES381583A1 (es) | 1972-11-16 |
| FR2059498A1 (enrdf_load_stackoverflow) | 1971-06-04 |
| NL7009808A (enrdf_load_stackoverflow) | 1971-01-12 |
| SU370772A3 (enrdf_load_stackoverflow) | 1973-02-15 |
| CH517067A (de) | 1971-12-31 |
| ZA704720B (en) | 1971-03-31 |
| CH517064A (de) | 1971-12-31 |
| ES381578A1 (es) | 1972-11-16 |
| ES381580A1 (es) | 1972-11-16 |
| US3743663A (en) | 1973-07-03 |
| CH517688A (de) | 1972-01-15 |
| AU1728970A (en) | 1972-01-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |