DE1793381C - - Google Patents
Info
- Publication number
- DE1793381C DE1793381C DE1793381C DE 1793381 C DE1793381 C DE 1793381C DE 1793381 C DE1793381 C DE 1793381C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- oxo
- benzyl
- cyclohexanepropionic
- solution
- 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.)
- Active
Links
- -1 2 - Oxo -1 - benzyl - cyclohexanepropionic acid sodium salt Chemical compound 0.000 claims description 14
- QQWBGHWKTDIMCX-UHFFFAOYSA-N 3-(1-benzyl-2-oxocyclohexyl)propanoic acid Chemical class C=1C=CC=CC=1CC1(CCC(=O)O)CCCCC1=O QQWBGHWKTDIMCX-UHFFFAOYSA-N 0.000 claims description 14
- 239000011780 sodium chloride Substances 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atoms Chemical class [H]* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- 239000002253 acid Substances 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 210000000941 Bile Anatomy 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- OVGORFFCBUIFIA-UHFFFAOYSA-N 1-phenylpentan-1-ol Chemical compound CCCCC(O)C1=CC=CC=C1 OVGORFFCBUIFIA-UHFFFAOYSA-N 0.000 description 5
- 230000001989 choleretic Effects 0.000 description 5
- 125000001664 diethylamino group Chemical class [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butanoic acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000000731 choleretic agent Substances 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- CUYLPYBYCYQGCE-UHFFFAOYSA-N 2-benzylcyclohexan-1-one Chemical compound O=C1CCCCC1CC1=CC=CC=C1 CUYLPYBYCYQGCE-UHFFFAOYSA-N 0.000 description 2
- IBAJWKQKPIIFQU-UHFFFAOYSA-N 2-methoxypropan-2-ylcyclohexane Chemical compound COC(C)(C)C1CCCCC1 IBAJWKQKPIIFQU-UHFFFAOYSA-N 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M Benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- IOOMCNWJDOMAPZ-UHFFFAOYSA-N C(CC)(=O)O.C(C1=CC=CC=C1)C1CCCCC1 Chemical compound C(CC)(=O)O.C(C1=CC=CC=C1)C1CCCCC1 IOOMCNWJDOMAPZ-UHFFFAOYSA-N 0.000 description 2
- 210000001953 Common Bile Duct Anatomy 0.000 description 2
- 229960002997 Dehydrocholic Acid Drugs 0.000 description 2
- OHXPGWPVLFPUSM-KLRNGDHRSA-N Dehydrocholic acid Chemical compound C1CC(=O)C[C@H]2CC(=O)[C@H]3[C@@H]4CC[C@H]([C@@H](CCC(O)=O)C)[C@@]4(C)C(=O)C[C@@H]3[C@]21C OHXPGWPVLFPUSM-KLRNGDHRSA-N 0.000 description 2
- 230000036826 Excretion Effects 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012259 ether extract Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- IYXQRCXQQWUFQV-RDJMKVHDSA-N (3R,5R)-1,4-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-3,5-dihydroxycyclohexane-1-carboxylic acid Chemical compound C1([C@H](O)CC(C[C@H]1O)(OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C(O)=O)OC(=O)\C=C\C1=CC=C(O)C(O)=C1 IYXQRCXQQWUFQV-RDJMKVHDSA-N 0.000 description 1
- YDDUMTOHNYZQPO-RVXRWRFUSA-N 1,3-dicaffeoylquinic acid Chemical compound O([C@@H]1C[C@@](C[C@H]([C@@H]1O)O)(OC(=O)\C=C\C=1C=C(O)C(O)=CC=1)C(O)=O)C(=O)\C=C\C1=CC=C(O)C(O)=C1 YDDUMTOHNYZQPO-RVXRWRFUSA-N 0.000 description 1
- HPLFQKUIHGZHPH-UHFFFAOYSA-N 2-(1-hydroxy-4-phenylcyclohexyl)butanoic acid Chemical compound C1CC(C(C(O)=O)CC)(O)CCC1C1=CC=CC=C1 HPLFQKUIHGZHPH-UHFFFAOYSA-N 0.000 description 1
- OYYZUAGSPRPUCK-UHFFFAOYSA-N 2-[(2-chlorophenyl)methyl]cyclohexan-1-one Chemical compound ClC1=CC=CC=C1CC1C(=O)CCCC1 OYYZUAGSPRPUCK-UHFFFAOYSA-N 0.000 description 1
- XEBOVYWLIDTDQE-UHFFFAOYSA-N 3-[1-[(2-chlorophenyl)methyl]-2-oxocyclohexyl]propanoic acid Chemical compound C=1C=CC=C(Cl)C=1CC1(CCC(=O)O)CCCCC1=O XEBOVYWLIDTDQE-UHFFFAOYSA-N 0.000 description 1
- BQRWJPVPSAFIRY-UHFFFAOYSA-N 3-[1-[(2-methoxyphenyl)methyl]-2-oxocyclohexyl]propanoic acid Chemical compound COC1=CC=CC=C1CC1(CCC(O)=O)C(=O)CCCC1 BQRWJPVPSAFIRY-UHFFFAOYSA-N 0.000 description 1
- 229960000583 Acetic Acid Drugs 0.000 description 1
- UEHKDTFMDMCQOE-UHFFFAOYSA-N C(CC)(=O)O.O=C1C(CCCC1)CC1=CC=CC=C1 Chemical compound C(CC)(=O)O.O=C1C(CCCC1)CC1=CC=CC=C1 UEHKDTFMDMCQOE-UHFFFAOYSA-N 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M Copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- NIVFTEMPSCMWDE-UHFFFAOYSA-N Cyclobutyrol Chemical compound CCC(C(O)=O)C1(O)CCCCC1 NIVFTEMPSCMWDE-UHFFFAOYSA-N 0.000 description 1
- HJZLEGIHUQOJBA-UHFFFAOYSA-N Cyclohexane Propionic Acid Chemical class OC(=O)CCC1CCCCC1 HJZLEGIHUQOJBA-UHFFFAOYSA-N 0.000 description 1
- 229950009125 Cynarine Drugs 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N Diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229950000795 Fencibutirol Drugs 0.000 description 1
- 239000004698 Polyethylene (PE) Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N Sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000008845 cholagoga Substances 0.000 description 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- HXXRFEYZOBSAJK-UHFFFAOYSA-N hexane;propanoic acid Chemical compound CCC(O)=O.CCCCCC HXXRFEYZOBSAJK-UHFFFAOYSA-N 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
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- VJINJXFHNHCOOT-UHFFFAOYSA-L magnesium;4-(4-methoxynaphthalen-1-yl)-4-oxobutanoate Chemical group [Mg+2].C1=CC=C2C(OC)=CC=C(C(=O)CCC([O-])=O)C2=C1.C1=CC=C2C(OC)=CC=C(C(=O)CCC([O-])=O)C2=C1 VJINJXFHNHCOOT-UHFFFAOYSA-L 0.000 description 1
- KQEVIFKPZOGBMZ-UHFFFAOYSA-N methyl 3-bromopropanoate Chemical compound COC(=O)CCBr KQEVIFKPZOGBMZ-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 230000000802 nitrating Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002035 prolonged Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Family
ID=
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