JPS5848545B2 - シンキホウコウゾクカルボンサンアミドユウドウタイ ノ セイゾウホウホウ - Google Patents
シンキホウコウゾクカルボンサンアミドユウドウタイ ノ セイゾウホウホウInfo
- Publication number
- JPS5848545B2 JPS5848545B2 JP4367374A JP4367374A JPS5848545B2 JP S5848545 B2 JPS5848545 B2 JP S5848545B2 JP 4367374 A JP4367374 A JP 4367374A JP 4367374 A JP4367374 A JP 4367374A JP S5848545 B2 JPS5848545 B2 JP S5848545B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- hydrogen
- group
- compound
- general formula
- 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
- 229910052799 carbon Inorganic materials 0.000 title description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 150000002148 esters Chemical class 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- ALYNCZNDIQEVRV-UHFFFAOYSA-N 4-aminobenzoic acid Chemical compound NC1=CC=C(C(O)=O)C=C1 ALYNCZNDIQEVRV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 229960004050 aminobenzoic acid Drugs 0.000 claims description 4
- 238000007796 conventional method Methods 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 description 68
- -1 derivatives of aromatic carboxylic acids Chemical class 0.000 description 55
- 239000001257 hydrogen Substances 0.000 description 54
- 150000001875 compounds Chemical class 0.000 description 34
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 239000007795 chemical reaction product Substances 0.000 description 16
- 239000013078 crystal Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 14
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 238000000862 absorption spectrum Methods 0.000 description 13
- 238000000921 elemental analysis Methods 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 230000002378 acidificating effect Effects 0.000 description 11
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 238000010992 reflux Methods 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 229940102398 methyl anthranilate Drugs 0.000 description 7
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- HJBWJAPEBGSQPR-GQCTYLIASA-N 3,4-dimethoxycinnamic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1OC HJBWJAPEBGSQPR-GQCTYLIASA-N 0.000 description 4
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical class OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 4
- HJBWJAPEBGSQPR-UHFFFAOYSA-N DMCA Natural products COC1=CC=C(C=CC(O)=O)C=C1OC HJBWJAPEBGSQPR-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 4
- 235000010233 benzoic acid Nutrition 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001336 alkenes Chemical class 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 235000013985 cinnamic acid Nutrition 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 description 2
- ZDIYGBWFISUTHI-GQCTYLIASA-N (e)-3-(3,4-diacetyloxyphenyl)prop-2-enoic acid Chemical compound CC(=O)OC1=CC=C(\C=C\C(O)=O)C=C1OC(C)=O ZDIYGBWFISUTHI-GQCTYLIASA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- AJHPGXZOIAYYDW-UHFFFAOYSA-N 3-(2-cyanophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CC1=CC=CC=C1C#N AJHPGXZOIAYYDW-UHFFFAOYSA-N 0.000 description 2
- BJJQJLOZWBZEGA-UHFFFAOYSA-N 3-Methoxybenzenepropanoic acid Chemical compound COC1=CC=CC(CCC(O)=O)=C1 BJJQJLOZWBZEGA-UHFFFAOYSA-N 0.000 description 2
- LZPNXAULYJPXEH-AATRIKPKSA-N 3-Methoxycinnamic acid Chemical compound COC1=CC=CC(\C=C\C(O)=O)=C1 LZPNXAULYJPXEH-AATRIKPKSA-N 0.000 description 2
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- IHKNVZISLLDMOR-UHFFFAOYSA-N O-Acetylferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1OC(C)=O IHKNVZISLLDMOR-UHFFFAOYSA-N 0.000 description 2
- IHKNVZISLLDMOR-GQCTYLIASA-N O-acetylferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1OC(C)=O IHKNVZISLLDMOR-GQCTYLIASA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- TXHWYSOQHNMOOU-UHFFFAOYSA-N chloro(diethoxy)phosphane Chemical compound CCOP(Cl)OCC TXHWYSOQHNMOOU-UHFFFAOYSA-N 0.000 description 2
- LXHWDUISRBUGRA-UHFFFAOYSA-N dichloro(phenoxy)phosphane Chemical compound ClP(Cl)OC1=CC=CC=C1 LXHWDUISRBUGRA-UHFFFAOYSA-N 0.000 description 2
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 2
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000007530 organic bases Chemical group 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000010647 peptide synthesis reaction Methods 0.000 description 2
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- OSGFGNDMDFEDTP-UHFFFAOYSA-N (2-chlorophenyl)-(4,5-dichloroimidazol-1-yl)methanone Chemical compound ClC1=C(Cl)N=CN1C(=O)C1=CC=CC=C1Cl OSGFGNDMDFEDTP-UHFFFAOYSA-N 0.000 description 1
- YIKHDPHTFYWYJV-GQCTYLIASA-N (e)-3-(2,4-dimethoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C(OC)=C1 YIKHDPHTFYWYJV-GQCTYLIASA-N 0.000 description 1
- UXOWQQCLBQBRMQ-VOTSOKGWSA-N (e)-3-(2-acetyloxyphenyl)prop-2-enoic acid Chemical compound CC(=O)OC1=CC=CC=C1\C=C\C(O)=O UXOWQQCLBQBRMQ-VOTSOKGWSA-N 0.000 description 1
- VLSRUFWCGBMYDJ-ONEGZZNKSA-N (e)-3-(3,5-dimethoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC(OC)=CC(\C=C\C(O)=O)=C1 VLSRUFWCGBMYDJ-ONEGZZNKSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- YZBOZNXACBQJHI-UHFFFAOYSA-N 1-dichlorophosphoryloxyethane Chemical compound CCOP(Cl)(Cl)=O YZBOZNXACBQJHI-UHFFFAOYSA-N 0.000 description 1
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 1
- LRQJURLTJGJOHF-UHFFFAOYSA-N 2,3-diethoxy-3-phenylprop-2-enoic acid Chemical compound C(C)OC(=C(C(=O)O)OCC)C1=CC=CC=C1 LRQJURLTJGJOHF-UHFFFAOYSA-N 0.000 description 1
- KMWSGKPLIWNTEF-UHFFFAOYSA-N 2-chloro-1,3,2$l^{5}-benzodioxaphosphole 2-oxide Chemical compound C1=CC=C2OP(Cl)(=O)OC2=C1 KMWSGKPLIWNTEF-UHFFFAOYSA-N 0.000 description 1
- YUJYEGDMJZHLMY-UHFFFAOYSA-N 2-chloro-1,3,2-benzodioxaphosphole Chemical compound C1=CC=C2OP(Cl)OC2=C1 YUJYEGDMJZHLMY-UHFFFAOYSA-N 0.000 description 1
- OLSFRDLMFAOSIA-UHFFFAOYSA-N 2-chloro-1,3,2-dioxaphospholane Chemical compound ClP1OCCO1 OLSFRDLMFAOSIA-UHFFFAOYSA-N 0.000 description 1
- YTFVRYKNXDADBI-SNAWJCMRSA-N 3,4,5-trimethoxycinnamic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC(OC)=C1OC YTFVRYKNXDADBI-SNAWJCMRSA-N 0.000 description 1
- MFFCZSWTQMCKFP-OWOJBTEDSA-N 3,5-dihydroxycinnamic acid Chemical compound OC(=O)\C=C\C1=CC(O)=CC(O)=C1 MFFCZSWTQMCKFP-OWOJBTEDSA-N 0.000 description 1
- VZFPHVWLPRCAGD-AATRIKPKSA-N 3-(2-Hydroxy-3-methoxyphenyl)-2-propenoic acid Chemical compound COC1=CC=CC(\C=C\C(O)=O)=C1O VZFPHVWLPRCAGD-AATRIKPKSA-N 0.000 description 1
- FXNNIQRXQQHHLV-UHFFFAOYSA-N 3-(2-ethoxy-3-methoxyphenyl)prop-2-enoic acid Chemical compound CCOC1=C(OC)C=CC=C1C=CC(O)=O FXNNIQRXQQHHLV-UHFFFAOYSA-N 0.000 description 1
- UMHUEEUKPMGPIL-UHFFFAOYSA-N 3-(2-ethoxy-3-methoxyphenyl)propanoic acid Chemical compound CCOC1=C(CCC(O)=O)C=CC=C1OC UMHUEEUKPMGPIL-UHFFFAOYSA-N 0.000 description 1
- UIZJAJLWHZFNRX-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)propanoic acid Chemical compound COC1=CC=CC(CCC(O)=O)=C1O UIZJAJLWHZFNRX-UHFFFAOYSA-N 0.000 description 1
- NWWYVWYCLMZXLU-UHFFFAOYSA-N 3-(3,4-diacetyloxyphenyl)propanoic acid Chemical compound CC(=O)OC1=CC=C(CCC(O)=O)C=C1OC(C)=O NWWYVWYCLMZXLU-UHFFFAOYSA-N 0.000 description 1
- UEEXLAGLYZFQIE-UHFFFAOYSA-N 3-(3,4-dipropoxyphenyl)prop-2-enoic acid Chemical compound CCCOC1=CC=C(C=CC(O)=O)C=C1OCCC UEEXLAGLYZFQIE-UHFFFAOYSA-N 0.000 description 1
- JSQCZLSYRUGLQC-UHFFFAOYSA-N 3-(3,5-diethoxyphenyl)propanoic acid Chemical compound CCOC1=CC(CCC(O)=O)=CC(OCC)=C1 JSQCZLSYRUGLQC-UHFFFAOYSA-N 0.000 description 1
- LMBOJOXVLORKSQ-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)propanoic acid Chemical compound COC1=CC(CCC(O)=O)=CC(OC)=C1 LMBOJOXVLORKSQ-UHFFFAOYSA-N 0.000 description 1
- HUSAGMYPWSUOFQ-UHFFFAOYSA-N 3-(3-acetyloxy-4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(C=CC(O)=O)C=C1OC(C)=O HUSAGMYPWSUOFQ-UHFFFAOYSA-N 0.000 description 1
- OBWBKPZBQCSHTL-UHFFFAOYSA-N 3-(3-ethoxy-4-methoxyphenyl)prop-2-enoic acid Chemical compound CCOC1=CC(C=CC(O)=O)=CC=C1OC OBWBKPZBQCSHTL-UHFFFAOYSA-N 0.000 description 1
- XOHHVCSPHJILQB-UHFFFAOYSA-N 3-(3-ethoxy-4-methoxyphenyl)propanoic acid Chemical compound CCOC1=CC(CCC(O)=O)=CC=C1OC XOHHVCSPHJILQB-UHFFFAOYSA-N 0.000 description 1
- KPSQXFCUDMQQNG-UHFFFAOYSA-N 3-(3-methoxy-2-propoxyphenyl)prop-2-enoic acid Chemical compound CCCOC1=C(OC)C=CC=C1C=CC(O)=O KPSQXFCUDMQQNG-UHFFFAOYSA-N 0.000 description 1
- UCXKEROBOPLEEV-UHFFFAOYSA-N 3-(3-methoxy-2-propoxyphenyl)propanoic acid Chemical compound CCCOC1=C(CCC(O)=O)C=CC=C1OC UCXKEROBOPLEEV-UHFFFAOYSA-N 0.000 description 1
- HCIFIHNJOLFAAX-UHFFFAOYSA-N 3-(3-methoxy-4-propan-2-yloxyphenyl)prop-2-enoic acid Chemical compound COC1=CC(C=CC(O)=O)=CC=C1OC(C)C HCIFIHNJOLFAAX-UHFFFAOYSA-N 0.000 description 1
- RLAQRGMUUSGHQC-UHFFFAOYSA-N 3-(3-methoxy-4-propan-2-yloxyphenyl)propanoic acid Chemical compound COC1=CC(CCC(O)=O)=CC=C1OC(C)C RLAQRGMUUSGHQC-UHFFFAOYSA-N 0.000 description 1
- QLWJYHRZUFQUDK-UHFFFAOYSA-N 3-(3-methoxy-4-propoxyphenyl)prop-2-enoic acid Chemical compound CCCOC1=CC=C(C=CC(O)=O)C=C1OC QLWJYHRZUFQUDK-UHFFFAOYSA-N 0.000 description 1
- RHGLPWUVIKZTEL-UHFFFAOYSA-N 3-(3-methoxy-4-propoxyphenyl)propanoic acid Chemical compound CCCOC1=CC=C(CCC(O)=O)C=C1OC RHGLPWUVIKZTEL-UHFFFAOYSA-N 0.000 description 1
- QOKSGDLEBVRINF-UHFFFAOYSA-N 3-(4-acetyloxy-3-methoxyphenyl)propanoic acid Chemical compound COC1=CC(CCC(O)=O)=CC=C1OC(C)=O QOKSGDLEBVRINF-UHFFFAOYSA-N 0.000 description 1
- BTKVFGHQNRGQIB-UHFFFAOYSA-N 3-(4-ethoxy-3-methoxyphenyl)propanoic acid Chemical compound CCOC1=CC=C(CCC(O)=O)C=C1OC BTKVFGHQNRGQIB-UHFFFAOYSA-N 0.000 description 1
- QQYITMPFOSACLW-UHFFFAOYSA-N 3-(4-methoxy-3-propoxyphenyl)prop-2-enoic acid Chemical compound CCCOC1=CC(C=CC(O)=O)=CC=C1OC QQYITMPFOSACLW-UHFFFAOYSA-N 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 1
- BYHMLZGICSEKIY-UHFFFAOYSA-N 3-amino-2-methylbenzoic acid Chemical compound CC1=C(N)C=CC=C1C(O)=O BYHMLZGICSEKIY-UHFFFAOYSA-N 0.000 description 1
- BYHBHNKBISXCEP-QPJJXVBHSA-N 4-acetoxycinnamic acid Chemical compound CC(=O)OC1=CC=C(\C=C\C(O)=O)C=C1 BYHBHNKBISXCEP-QPJJXVBHSA-N 0.000 description 1
- ALYNCZNDIQEVRV-PZFLKRBQSA-N 4-amino-3,5-ditritiobenzoic acid Chemical compound [3H]c1cc(cc([3H])c1N)C(O)=O ALYNCZNDIQEVRV-PZFLKRBQSA-N 0.000 description 1
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 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
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- YTFVRYKNXDADBI-UHFFFAOYSA-N O-Methylsinapic acid Natural products COC1=CC(C=CC(O)=O)=CC(OC)=C1OC YTFVRYKNXDADBI-UHFFFAOYSA-N 0.000 description 1
- 241001483078 Phyto Species 0.000 description 1
- QPQGTZMAQRXCJW-UHFFFAOYSA-N [chloro(phenyl)phosphoryl]benzene Chemical compound C=1C=CC=CC=1P(=O)(Cl)C1=CC=CC=C1 QPQGTZMAQRXCJW-UHFFFAOYSA-N 0.000 description 1
- ZVQOOHYFBIDMTQ-UHFFFAOYSA-N [methyl(oxido){1-[6-(trifluoromethyl)pyridin-3-yl]ethyl}-lambda(6)-sulfanylidene]cyanamide Chemical compound N#CN=S(C)(=O)C(C)C1=CC=C(C(F)(F)F)N=C1 ZVQOOHYFBIDMTQ-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000005427 anthranyl group Chemical group 0.000 description 1
- 230000003266 anti-allergic effect Effects 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N beta-methyl-butyric acid Natural products CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001727 carbonic acid monoesters Chemical class 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- 150000001731 carboxylic acid azides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- NNPCWHQMEPPTJV-UHFFFAOYSA-N chloro(dimethoxy)phosphane Chemical compound COP(Cl)OC NNPCWHQMEPPTJV-UHFFFAOYSA-N 0.000 description 1
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- PVCINRPAXRJLEP-UHFFFAOYSA-N dichloro(ethoxy)phosphane Chemical compound CCOP(Cl)Cl PVCINRPAXRJLEP-UHFFFAOYSA-N 0.000 description 1
- HCSDJECSMANTCX-UHFFFAOYSA-N dichloro(methoxy)phosphane Chemical compound COP(Cl)Cl HCSDJECSMANTCX-UHFFFAOYSA-N 0.000 description 1
- TXFOLHZMICYNRM-UHFFFAOYSA-N dichlorophosphoryloxybenzene Chemical compound ClP(Cl)(=O)OC1=CC=CC=C1 TXFOLHZMICYNRM-UHFFFAOYSA-N 0.000 description 1
- BOLQJTPHPSDZHR-UHFFFAOYSA-N dihydroferulic acid Chemical compound COC1=CC(CCC(O)=O)=CC=C1O BOLQJTPHPSDZHR-UHFFFAOYSA-N 0.000 description 1
- ZVIJTQFTLXXGJA-UHFFFAOYSA-N dihydroisoferulic acid Chemical compound COC1=CC=C(CCC(O)=O)C=C1O ZVIJTQFTLXXGJA-UHFFFAOYSA-N 0.000 description 1
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- UJQMLHKSZKBMMO-UHFFFAOYSA-N n,n-diethylethanamine;pyridine Chemical compound C1=CC=NC=C1.CCN(CC)CC UJQMLHKSZKBMMO-UHFFFAOYSA-N 0.000 description 1
- AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- KKSDGJDHHZEWEP-SNAWJCMRSA-N trans-3-coumaric acid Chemical compound OC(=O)\C=C\C1=CC=CC(O)=C1 KKSDGJDHHZEWEP-SNAWJCMRSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
Landscapes
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Pyrane Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4367374A JPS5848545B2 (ja) | 1974-04-18 | 1974-04-18 | シンキホウコウゾクカルボンサンアミドユウドウタイ ノ セイゾウホウホウ |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4367374A JPS5848545B2 (ja) | 1974-04-18 | 1974-04-18 | シンキホウコウゾクカルボンサンアミドユウドウタイ ノ セイゾウホウホウ |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS50140413A JPS50140413A (enrdf_load_stackoverflow) | 1975-11-11 |
| JPS5848545B2 true JPS5848545B2 (ja) | 1983-10-28 |
Family
ID=12670346
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4367374A Expired JPS5848545B2 (ja) | 1974-04-18 | 1974-04-18 | シンキホウコウゾクカルボンサンアミドユウドウタイ ノ セイゾウホウホウ |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5848545B2 (enrdf_load_stackoverflow) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5838244A (ja) * | 1981-09-01 | 1983-03-05 | Kissei Pharmaceut Co Ltd | 核置換シンナモイルアントラニル酸塩およびその製造方法 |
| JPS60146856A (ja) * | 1983-12-30 | 1985-08-02 | Kissei Pharmaceut Co Ltd | α−ハロ芳香族アミドカルボン酸誘導体及びこの化合物より成る抗アレルギ−剤 |
| JPS60146857A (ja) * | 1983-12-30 | 1985-08-02 | Kissei Pharmaceut Co Ltd | α−ハロ芳香族アミドカルボン酸誘導体及びこの化合物より成る抗アレルギ−剤 |
| JPH064584B2 (ja) * | 1984-02-29 | 1994-01-19 | 沢井製薬株式会社 | 新規アニリド誘導体 |
| FR2759368B1 (fr) * | 1997-02-10 | 2001-06-01 | Galderma Rech Dermatologique | Composes biaromatiques, compositions les contenant et utilisations |
| DE19935219A1 (de) * | 1999-07-27 | 2001-02-01 | Boehringer Ingelheim Pharma | Carbonsäureamide, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Herstellung |
| FR2835253B1 (fr) * | 2002-01-31 | 2008-02-01 | Pape Patrice Le | Composes, en particulier de derives urees ou esters de l'acide haloacetamidobenzoique et leur utilisation pour le traitement de maladies parasitaires |
| LT2799427T (lt) | 2006-07-05 | 2018-11-26 | Fibrotech Therapeutics Pty Ltd | Terapiniai junginiai |
| KR101593708B1 (ko) | 2007-12-21 | 2016-02-12 | 피브로테크 세라퓨틱 피티와이 엘티디 | 항섬유증 제제의 할로겐화 유사체 |
| WO2011047432A1 (en) | 2009-10-22 | 2011-04-28 | Fibrotech Therapeutics Pty Ltd | Fused ring analogues of anti-fibrotic agents |
| CA3052036A1 (en) | 2017-02-03 | 2018-08-09 | Certa Therapeutics Pty Ltd. | Anti-fibrotic compounds |
| US11078155B2 (en) * | 2018-08-14 | 2021-08-03 | Nuformix Technologies Limited | Crystalline tranilast salts and their pharmaceutical use |
-
1974
- 1974-04-18 JP JP4367374A patent/JPS5848545B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| JPS50140413A (enrdf_load_stackoverflow) | 1975-11-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| WO1991014673A1 (fr) | Procede nouveau pour fabriquer un derive d'acide benzoique | |
| JPS5848545B2 (ja) | シンキホウコウゾクカルボンサンアミドユウドウタイ ノ セイゾウホウホウ | |
| CN112174989A (zh) | 一种克立硼罗的制备方法 | |
| JPH01211567A (ja) | 新規なスルホンアミド化合物 | |
| CN103910671B (zh) | Vismodegib及其中间体的制备方法 | |
| JPS5830302B2 (ja) | シンキホウコウゾクカルボンサンアミドユウドウタイ ノ セイゾウホウホウ | |
| CN114105984A (zh) | 吲哚嗪类抗蚀剂的制备方法 | |
| JPS5817186B2 (ja) | 新規芳香族カルボン酸誘導体の製造方法 | |
| JPH01265074A (ja) | 新規な７―アシルインドール誘導体 | |
| SU512697A3 (ru) | Способ получени бензиламинов | |
| JPS6115882A (ja) | Ｎ−アシル−２，６−キシリジン誘導体 | |
| CN100522907C (zh) | 一羟基芳族化合物的二聚体的制备方法 | |
| JPS5927343B2 (ja) | ３−アミノイソオキサゾ−ル類の合成法 | |
| US3240784A (en) | Esters of quaternary z-hydroxy methyl piperidinium compounds | |
| JPS604163A (ja) | スルフアイド化合物 | |
| JPS5838261A (ja) | 新規な１，３−二置換イミダゾ−ル誘導体及びその製造方法 | |
| JPH06508851A (ja) | １３α−シンナモイルバッカチンＩＩＩまたは−１０−デアセチルバッカチンＩＩＩの製造方法 | |
| JPS59122449A (ja) | 芳香族カルボン酸アミド誘導体の製造方法 | |
| Liu et al. | Microwave-assisted synthesis and recognition properties of chiral molecular tweezers based on deoxycholic acid | |
| JPS61112056A (ja) | イミダゾ−ル誘導体及びその製法 | |
| JPS5848544B2 (ja) | Ｎ− チカンマロンサンアミドユウドウタイ ノ セイゾウホウホウ | |
| JPS6130660B2 (enrdf_load_stackoverflow) | ||
| CN120329233A (zh) | 乌帕替尼中间体的制备方法及其中间体 | |
| KR900001078B1 (ko) | 시클로 퀴놀론 유도체의 제조방법 | |
| JPH01238548A (ja) | ナフタレン―１，４，５，８―テトラカルボン酸テトラアルキルエステルの製造方法 |