CS199283B2 - Method of preparing aryloxyalkyl aminobenzoic acids and esters thereof - Google Patents
Method of preparing aryloxyalkyl aminobenzoic acids and esters thereof Download PDFInfo
- Publication number
- CS199283B2 CS199283B2 CS768014A CS801476A CS199283B2 CS 199283 B2 CS199283 B2 CS 199283B2 CS 768014 A CS768014 A CS 768014A CS 801476 A CS801476 A CS 801476A CS 199283 B2 CS199283 B2 CS 199283B2
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- CS
- Czechoslovakia
- Prior art keywords
- mixture
- ethyl
- water
- solution
- hours
- Prior art date
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- -1 aryloxyalkyl aminobenzoic acids Chemical class 0.000 title claims description 51
- 150000002148 esters Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 105
- 239000000203 mixture Substances 0.000 claims description 76
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 58
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 44
- 239000007787 solid Substances 0.000 claims description 38
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical class NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 238000002844 melting Methods 0.000 claims description 8
- 230000008018 melting Effects 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000002168 alkylating agent Substances 0.000 claims description 5
- 229940100198 alkylating agent Drugs 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000001816 cooling Methods 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000000843 powder Substances 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000004953 trihalomethyl group Chemical group 0.000 claims description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 57
- 239000000243 solution Substances 0.000 description 54
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
- 239000013078 crystal Substances 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 29
- 239000000047 product Substances 0.000 description 26
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 20
- 238000001953 recrystallisation Methods 0.000 description 18
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 15
- 235000019341 magnesium sulphate Nutrition 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 12
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 11
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 11
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 11
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 125000005160 aryl oxy alkyl group Chemical group 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 229940064734 aminobenzoate Drugs 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 4
- 239000005711 Benzoic acid Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 229930182558 Sterol Natural products 0.000 description 4
- 230000029936 alkylation Effects 0.000 description 4
- 238000005804 alkylation reaction Methods 0.000 description 4
- 150000005415 aminobenzoic acids Chemical class 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 210000002966 serum Anatomy 0.000 description 4
- 150000003432 sterols Chemical class 0.000 description 4
- 235000003702 sterols Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical class NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 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 3
- BFPFJPUHXMQFKT-UHFFFAOYSA-N ethyl 4-(3-phenoxypropylamino)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NCCCOC1=CC=CC=C1 BFPFJPUHXMQFKT-UHFFFAOYSA-N 0.000 description 3
- 230000000055 hyoplipidemic effect Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 150000003626 triacylglycerols Chemical class 0.000 description 3
- KHSYYLCXQKCYQX-UHFFFAOYSA-N 1-naphthalen-2-ylethanamine Chemical compound C1=CC=CC2=CC(C(N)C)=CC=C21 KHSYYLCXQKCYQX-UHFFFAOYSA-N 0.000 description 2
- PVPXWOAAXYWGNN-UHFFFAOYSA-N 11-phenoxyundecan-1-ol Chemical compound OCCCCCCCCCCCOC1=CC=CC=C1 PVPXWOAAXYWGNN-UHFFFAOYSA-N 0.000 description 2
- XIWVTXCMAXCPCT-UHFFFAOYSA-N 11-phenoxyundecyl methanesulfonate Chemical compound CS(=O)(=O)OCCCCCCCCCCCOC1=CC=CC=C1 XIWVTXCMAXCPCT-UHFFFAOYSA-N 0.000 description 2
- DVXLSPQJOMFKKF-UHFFFAOYSA-N 2,3-dihydroxypropyl 4-(3-phenoxypropylamino)benzoate Chemical compound C1=CC(C(=O)OCC(O)CO)=CC=C1NCCCOC1=CC=CC=C1 DVXLSPQJOMFKKF-UHFFFAOYSA-N 0.000 description 2
- DUCLMCMBTHOIAI-UHFFFAOYSA-N 2-(4-chlorophenoxy)propyl methanesulfonate Chemical compound CS(=O)(=O)OCC(C)OC1=CC=C(Cl)C=C1 DUCLMCMBTHOIAI-UHFFFAOYSA-N 0.000 description 2
- KJJLZIVJYUVYTR-UHFFFAOYSA-N 2-(4-fluorophenoxy)ethanol Chemical compound OCCOC1=CC=C(F)C=C1 KJJLZIVJYUVYTR-UHFFFAOYSA-N 0.000 description 2
- QUZSHRALJXOPFS-UHFFFAOYSA-N 2-(4-fluorophenoxy)propan-1-ol Chemical compound OCC(C)OC1=CC=C(F)C=C1 QUZSHRALJXOPFS-UHFFFAOYSA-N 0.000 description 2
- WIVLMXDHGGRLMP-UHFFFAOYSA-N 2-(4-fluorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(F)C=C1 WIVLMXDHGGRLMP-UHFFFAOYSA-N 0.000 description 2
- QRXLRRPTCPKNCC-UHFFFAOYSA-N 2-naphthalen-1-yloxyethyl methanesulfonate Chemical compound C1=CC=C2C(OCCOS(=O)(=O)C)=CC=CC2=C1 QRXLRRPTCPKNCC-UHFFFAOYSA-N 0.000 description 2
- LOJHHQNEBFCTQK-UHFFFAOYSA-N 2-phenoxypropan-1-ol Chemical compound OCC(C)OC1=CC=CC=C1 LOJHHQNEBFCTQK-UHFFFAOYSA-N 0.000 description 2
- OMCLFGKJUXKWRU-UHFFFAOYSA-N 2-phenoxypropyl methanesulfonate Chemical compound CS(=O)(=O)OCC(C)OC1=CC=CC=C1 OMCLFGKJUXKWRU-UHFFFAOYSA-N 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- IRTQUWPZPJDVPX-UHFFFAOYSA-N 3-(4-chlorophenoxy)propyl methanesulfonate Chemical compound CS(=O)(=O)OCCCOC1=CC=C(Cl)C=C1 IRTQUWPZPJDVPX-UHFFFAOYSA-N 0.000 description 2
- PZTAMYVDDKMLHV-UHFFFAOYSA-N 4-(11-phenoxyundecylamino)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NCCCCCCCCCCCOC1=CC=CC=C1 PZTAMYVDDKMLHV-UHFFFAOYSA-N 0.000 description 2
- PPASVIGUSAEUFJ-UHFFFAOYSA-N 4-(2-phenoxyethylamino)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NCCOC1=CC=CC=C1 PPASVIGUSAEUFJ-UHFFFAOYSA-N 0.000 description 2
- JEPGCYHWAKWKID-UHFFFAOYSA-N 4-(2-phenoxypropylamino)benzoic acid Chemical compound C=1C=CC=CC=1OC(C)CNC1=CC=C(C(O)=O)C=C1 JEPGCYHWAKWKID-UHFFFAOYSA-N 0.000 description 2
- RMVDFSUOWSZJJC-UHFFFAOYSA-N 4-(3-phenoxypropylamino)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NCCCOC1=CC=CC=C1 RMVDFSUOWSZJJC-UHFFFAOYSA-N 0.000 description 2
- JNTPTNNCGDAGEJ-UHFFFAOYSA-N 6-chlorohexan-1-ol Chemical compound OCCCCCCCl JNTPTNNCGDAGEJ-UHFFFAOYSA-N 0.000 description 2
- PVDHNBFKZKZOSO-UHFFFAOYSA-N 6-naphthalen-2-yloxyhexan-1-ol Chemical compound C1=CC=CC2=CC(OCCCCCCO)=CC=C21 PVDHNBFKZKZOSO-UHFFFAOYSA-N 0.000 description 2
- KGAAHYOKTFZJFD-UHFFFAOYSA-N 6-phenoxyhexan-1-ol Chemical compound OCCCCCCOC1=CC=CC=C1 KGAAHYOKTFZJFD-UHFFFAOYSA-N 0.000 description 2
- UKKCWEXFTCUHHL-UHFFFAOYSA-N 6-phenoxyhexyl methanesulfonate Chemical compound CS(=O)(=O)OCCCCCCOC1=CC=CC=C1 UKKCWEXFTCUHHL-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 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 2
- 229930006000 Sucrose Natural products 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229960004050 aminobenzoic acid Drugs 0.000 description 2
- 229950011260 betanaphthol Drugs 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001805 chlorine compounds Chemical class 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- AGVFWQPBGRCYBY-UHFFFAOYSA-N ethyl 4-(11-phenoxyundecylamino)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NCCCCCCCCCCCOC1=CC=CC=C1 AGVFWQPBGRCYBY-UHFFFAOYSA-N 0.000 description 2
- CYXKGJNVFAAGNH-UHFFFAOYSA-N ethyl 4-(2-phenoxyethylamino)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NCCOC1=CC=CC=C1 CYXKGJNVFAAGNH-UHFFFAOYSA-N 0.000 description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 229910052987 metal hydride Inorganic materials 0.000 description 2
- 150000004681 metal hydrides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 238000005932 reductive alkylation reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Inorganic materials [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- ULTHEAFYOOPTTB-UHFFFAOYSA-N 1,4-dibromobutane Chemical compound BrCCCCBr ULTHEAFYOOPTTB-UHFFFAOYSA-N 0.000 description 1
- MGAGSLFQCLCNKL-UHFFFAOYSA-N 1-bromo-3-propoxypropane Chemical compound CCCOCCCBr MGAGSLFQCLCNKL-UHFFFAOYSA-N 0.000 description 1
- SRGBSEMMGLSUMI-UHFFFAOYSA-N 1-bromo-4-(2-bromoethoxy)benzene Chemical compound BrCCOC1=CC=C(Br)C=C1 SRGBSEMMGLSUMI-UHFFFAOYSA-N 0.000 description 1
- VZLMIORNRMGZJC-UHFFFAOYSA-N 1-naphthalen-2-yloxyethanol Chemical compound C1=CC=CC2=CC(OC(O)C)=CC=C21 VZLMIORNRMGZJC-UHFFFAOYSA-N 0.000 description 1
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N 1-propanol Substances CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- IUDGNRWYNOEIKF-UHFFFAOYSA-N 11-bromo-undecanoic acid Chemical compound OC(=O)CCCCCCCCCCBr IUDGNRWYNOEIKF-UHFFFAOYSA-N 0.000 description 1
- ZBIULCVFFJJYTN-UHFFFAOYSA-N 2-(4-fluorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(F)C=C1 ZBIULCVFFJJYTN-UHFFFAOYSA-N 0.000 description 1
- TYLUJTIEHNATAM-UHFFFAOYSA-N 2-(4-phenylmethoxyphenoxy)propan-1-ol Chemical compound C1=CC(OC(CO)C)=CC=C1OCC1=CC=CC=C1 TYLUJTIEHNATAM-UHFFFAOYSA-N 0.000 description 1
- SXERGJJQSKIUIC-UHFFFAOYSA-N 2-Phenoxypropionic acid Chemical compound OC(=O)C(C)OC1=CC=CC=C1 SXERGJJQSKIUIC-UHFFFAOYSA-N 0.000 description 1
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 1
- JJFOBACUIRKUPN-UHFFFAOYSA-N 2-bromoethoxybenzene Chemical compound BrCCOC1=CC=CC=C1 JJFOBACUIRKUPN-UHFFFAOYSA-N 0.000 description 1
- MONMFXREYOKQTI-UHFFFAOYSA-N 2-bromopropanoic acid Chemical compound CC(Br)C(O)=O MONMFXREYOKQTI-UHFFFAOYSA-N 0.000 description 1
- IHQRCMUWPFBYLW-UHFFFAOYSA-N 2-methyl-2-(4-phenylmethoxyphenoxy)propanoic acid Chemical compound C1=CC(OC(C)(C)C(O)=O)=CC=C1OCC1=CC=CC=C1 IHQRCMUWPFBYLW-UHFFFAOYSA-N 0.000 description 1
- HCWJMLZCVUEYPO-UHFFFAOYSA-N 2-naphthalen-1-yloxyethanol Chemical compound C1=CC=C2C(OCCO)=CC=CC2=C1 HCWJMLZCVUEYPO-UHFFFAOYSA-N 0.000 description 1
- BQPBZDSDFCDSAO-UHFFFAOYSA-N 2-naphthalen-2-yloxyethanol Chemical compound C1=CC=CC2=CC(OCCO)=CC=C21 BQPBZDSDFCDSAO-UHFFFAOYSA-N 0.000 description 1
- RGBVJWZNBGQZTP-UHFFFAOYSA-N 2-naphthalen-2-yloxyethyl methanesulfonate Chemical compound C1=CC=CC2=CC(OCCOS(=O)(=O)C)=CC=C21 RGBVJWZNBGQZTP-UHFFFAOYSA-N 0.000 description 1
- VMJOFTHFJMLIKL-UHFFFAOYSA-N 2-thiophen-2-ylethanol Chemical compound OCCC1=CC=CS1 VMJOFTHFJMLIKL-UHFFFAOYSA-N 0.000 description 1
- VUMFRFIVUQTAPJ-UHFFFAOYSA-N 2-thiophen-2-ylethyl methanesulfonate Chemical compound CS(=O)(=O)OCCC1=CC=CS1 VUMFRFIVUQTAPJ-UHFFFAOYSA-N 0.000 description 1
- DMCGTVJRKBBDNM-UHFFFAOYSA-N 3-(4-chlorophenoxy)propan-1-ol Chemical compound OCCCOC1=CC=C(Cl)C=C1 DMCGTVJRKBBDNM-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- HJPNGEBNEGDLKU-UHFFFAOYSA-N 4-(2-naphthalen-2-yloxyethylamino)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NCCOC1=CC=C(C=CC=C2)C2=C1 HJPNGEBNEGDLKU-UHFFFAOYSA-N 0.000 description 1
- ABRFIWBGXBHPGF-UHFFFAOYSA-N 4-(4-phenoxybutylamino)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NCCCCOC1=CC=CC=C1 ABRFIWBGXBHPGF-UHFFFAOYSA-N 0.000 description 1
- SFQDEETZVKZXNH-UHFFFAOYSA-N 4-(6-phenoxyhexylamino)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NCCCCCCOC1=CC=CC=C1 SFQDEETZVKZXNH-UHFFFAOYSA-N 0.000 description 1
- BJYWFTMCEMOMKQ-UHFFFAOYSA-N 4-(hexadecanoylamino)benzoic acid Chemical compound CCCCCCCCCCCCCCCC(=O)NC1=CC=C(C(O)=O)C=C1 BJYWFTMCEMOMKQ-UHFFFAOYSA-N 0.000 description 1
- QXWKHSSBFQDQPR-UHFFFAOYSA-N 4-(hexadecylamino)benzoic acid Chemical compound CCCCCCCCCCCCCCCCNC1=CC=C(C(O)=O)C=C1 QXWKHSSBFQDQPR-UHFFFAOYSA-N 0.000 description 1
- SLJVKPULEZEMQO-UHFFFAOYSA-N 4-[2-(2,4-dichlorophenoxy)ethylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NCCOC1=CC=C(Cl)C=C1Cl SLJVKPULEZEMQO-UHFFFAOYSA-N 0.000 description 1
- UZQISPVDSZBOTB-UHFFFAOYSA-N 4-[2-(4-fluorophenoxy)propylamino]benzoic acid Chemical compound C=1C=C(F)C=CC=1OC(C)CNC1=CC=C(C(O)=O)C=C1 UZQISPVDSZBOTB-UHFFFAOYSA-N 0.000 description 1
- YMWURYHJQWKSDD-UHFFFAOYSA-N 4-[3-(4-chlorophenoxy)propylamino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NCCCOC1=CC=C(Cl)C=C1 YMWURYHJQWKSDD-UHFFFAOYSA-N 0.000 description 1
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 1
- CYYSMKXETNAWMU-UHFFFAOYSA-N 6-naphthalen-2-yloxyhexyl methanesulfonate Chemical compound C1=CC=CC2=CC(OCCCCCCOS(=O)(=O)C)=CC=C21 CYYSMKXETNAWMU-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
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 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 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
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- 241000124008 Mammalia Species 0.000 description 1
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000004442 acylamino group Chemical group 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000003524 antilipemic agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- FXCLIEYDXXVEAI-UHFFFAOYSA-N benzene;dichloromethane Chemical compound ClCCl.C1=CC=CC=C1 FXCLIEYDXXVEAI-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- 239000007958 cherry flavor Substances 0.000 description 1
- 235000015218 chewing gum Nutrition 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- NPOMSUOUAZCMBL-UHFFFAOYSA-N dichloromethane;ethoxyethane Chemical compound ClCCl.CCOCC NPOMSUOUAZCMBL-UHFFFAOYSA-N 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- LMKYBAPDSOHWRD-UHFFFAOYSA-N ethyl 2-(4-phenylmethoxyphenoxy)propanoate Chemical compound C1=CC(OC(C)C(=O)OCC)=CC=C1OCC1=CC=CC=C1 LMKYBAPDSOHWRD-UHFFFAOYSA-N 0.000 description 1
- IOLQWGVDEFWYNP-UHFFFAOYSA-N ethyl 2-bromo-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)Br IOLQWGVDEFWYNP-UHFFFAOYSA-N 0.000 description 1
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
- QWSTWDSYGCHYEJ-UHFFFAOYSA-N ethyl 4-(6-phenoxyhexylamino)benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NCCCCCCOC1=CC=CC=C1 QWSTWDSYGCHYEJ-UHFFFAOYSA-N 0.000 description 1
- XRBOKBDWIVSMAY-UHFFFAOYSA-N ethyl 4-(hexadecanoylamino)benzoate Chemical compound CCCCCCCCCCCCCCCC(=O)NC1=CC=C(C(=O)OCC)C=C1 XRBOKBDWIVSMAY-UHFFFAOYSA-N 0.000 description 1
- VCFLGAOCYOZUMD-UHFFFAOYSA-N ethyl 4-(hexadecylamino)benzoate Chemical compound CCCCCCCCCCCCCCCCNC1=CC=C(C(=O)OCC)C=C1 VCFLGAOCYOZUMD-UHFFFAOYSA-N 0.000 description 1
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000012041 food component Nutrition 0.000 description 1
- 239000005417 food ingredient Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-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
- 239000003701 inert diluent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 229960000990 monobenzone Drugs 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000003755 preservative agent 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
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 235000012431 wafers Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- 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
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
-
- 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
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Obesity (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Heart & Thoracic Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Furan Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63901875A | 1975-12-09 | 1975-12-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS199283B2 true CS199283B2 (en) | 1980-07-31 |
Family
ID=24562393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS768014A CS199283B2 (en) | 1975-12-09 | 1976-12-08 | Method of preparing aryloxyalkyl aminobenzoic acids and esters thereof |
Country Status (22)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9207855D0 (en) * | 1992-04-09 | 1992-05-27 | Ici Plc | Therapeutic amines |
| US5741926A (en) * | 1997-02-12 | 1998-04-21 | Shaman Pharmaceuticals, Inc. | Aniline derivatives having antihyperglycemic activity |
-
1976
- 1976-11-16 ZA ZA766847A patent/ZA766847B/xx unknown
- 1976-11-17 IL IL50926A patent/IL50926A/xx unknown
- 1976-11-19 IN IN2074/CAL/1976A patent/IN145203B/en unknown
- 1976-11-19 AU AU19831/76A patent/AU507077B2/en not_active Expired
- 1976-11-23 AR AR265570A patent/AR214187A1/es active
- 1976-12-02 DE DE19762654646 patent/DE2654646A1/de not_active Withdrawn
- 1976-12-03 GB GB50633/76A patent/GB1533647A/en not_active Expired
- 1976-12-07 AT AT907776A patent/AT358013B/de not_active IP Right Cessation
- 1976-12-08 RO RO7688674A patent/RO71276A/ro unknown
- 1976-12-08 CS CS768014A patent/CS199283B2/cs unknown
- 1976-12-08 DK DK550676A patent/DK550676A/da unknown
- 1976-12-08 SE SE7613808A patent/SE7613808L/xx not_active Application Discontinuation
- 1976-12-09 NL NL7613696A patent/NL7613696A/xx not_active Application Discontinuation
- 1976-12-09 BG BG034873A patent/BG27540A3/xx unknown
- 1976-12-09 DD DD7600196223A patent/DD128354A5/xx unknown
- 1976-12-09 PL PL1976194269A patent/PL109985B1/pl unknown
- 1976-12-09 ES ES454073A patent/ES454073A1/es not_active Expired
- 1976-12-09 SU SU762427095A patent/SU636225A1/ru active
- 1976-12-09 PT PT65945A patent/PT65945B/pt unknown
- 1976-12-09 FR FR7637076A patent/FR2334347A1/fr active Granted
- 1976-12-09 JP JP51148275A patent/JPS5273834A/ja active Pending
- 1976-12-09 BE BE173108A patent/BE849231A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AT358013B (de) | 1980-08-11 |
| AR214187A1 (es) | 1979-05-15 |
| AU1983176A (en) | 1978-05-25 |
| SE7613808L (sv) | 1977-06-10 |
| DK550676A (da) | 1977-06-10 |
| FR2334347A1 (fr) | 1977-07-08 |
| ATA907776A (de) | 1980-01-15 |
| IN145203B (enrdf_load_html_response) | 1978-09-09 |
| JPS5273834A (en) | 1977-06-21 |
| PT65945B (en) | 1978-06-14 |
| GB1533647A (en) | 1978-11-29 |
| ES454073A1 (es) | 1978-02-16 |
| IL50926A0 (en) | 1977-01-31 |
| BE849231A (fr) | 1977-06-09 |
| ZA766847B (en) | 1977-10-26 |
| BG27540A3 (en) | 1979-11-12 |
| PT65945A (en) | 1977-01-01 |
| SU636225A1 (ru) | 1978-12-05 |
| RO71276A (ro) | 1982-10-26 |
| FR2334347B1 (enrdf_load_html_response) | 1980-10-31 |
| PL194269A1 (pl) | 1978-06-05 |
| DD128354A5 (de) | 1977-11-16 |
| AU507077B2 (en) | 1980-01-31 |
| IL50926A (en) | 1980-12-31 |
| DE2654646A1 (de) | 1977-06-16 |
| NL7613696A (nl) | 1977-06-13 |
| PL109985B1 (en) | 1980-06-30 |
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