BE828003A - Nouveaux derives d'acides amidocarboxyliques aromatiques - Google Patents
Nouveaux derives d'acides amidocarboxyliques aromatiquesInfo
- Publication number
- BE828003A BE828003A BE155462A BE155462A BE828003A BE 828003 A BE828003 A BE 828003A BE 155462 A BE155462 A BE 155462A BE 155462 A BE155462 A BE 155462A BE 828003 A BE828003 A BE 828003A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- group
- acid
- carbon atoms
- general formula
- Prior art date
Links
- 239000002253 acid Substances 0.000 title description 50
- 150000007513 acids Chemical class 0.000 title description 21
- 150000001875 compounds Chemical class 0.000 claims description 63
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 11
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 238000012360 testing method Methods 0.000 claims description 5
- 125000002947 alkylene group Chemical group 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
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005702 oxyalkylene group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 208000010668 atopic eczema Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000035945 sensitivity Effects 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- 239000000203 mixture Substances 0.000 description 36
- 239000000243 solution Substances 0.000 description 29
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- 239000013078 crystal Substances 0.000 description 25
- 238000001914 filtration Methods 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 230000003266 anti-allergic effect Effects 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- -1 alkali metal salts Chemical class 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 7
- 230000002378 acidificating effect Effects 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 239000012467 final product Substances 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 206010020751 Hypersensitivity Diseases 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000001735 carboxylic acids Chemical class 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 3
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 206010002198 Anaphylactic reaction Diseases 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 230000007815 allergy Effects 0.000 description 3
- 230000036783 anaphylactic response Effects 0.000 description 3
- 208000003455 anaphylaxis Diseases 0.000 description 3
- 239000000427 antigen Substances 0.000 description 3
- 102000036639 antigens Human genes 0.000 description 3
- 108091007433 antigens Proteins 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 230000003389 potentiating effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 2
- CSEWAUGPAQPMDC-UHFFFAOYSA-N 2-(4-aminophenyl)acetic acid Chemical class NC1=CC=C(CC(O)=O)C=C1 CSEWAUGPAQPMDC-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- USZBUTFSZXTHPQ-UHFFFAOYSA-N 2-[2-[3-(3-methoxyphenyl)prop-2-enoylamino]phenyl]propanoic acid Chemical compound COC1=CC=CC(C=CC(=O)NC=2C(=CC=CC=2)C(C)C(O)=O)=C1 USZBUTFSZXTHPQ-UHFFFAOYSA-N 0.000 description 2
- SQBAMYXDIAGGLZ-UHFFFAOYSA-N 2-[2-[3-(4-methylphenyl)propanoylamino]phenyl]acetic acid Chemical compound C1=CC(C)=CC=C1CCC(=O)NC1=CC=CC=C1CC(O)=O SQBAMYXDIAGGLZ-UHFFFAOYSA-N 0.000 description 2
- IVACEVWMMBMPSM-UHFFFAOYSA-N 2-[3-[[3-(4-chlorophenyl)-2-methylprop-2-enoyl]amino]phenyl]acetic acid Chemical compound C=1C=CC(CC(O)=O)=CC=1NC(=O)C(C)=CC1=CC=C(Cl)C=C1 IVACEVWMMBMPSM-UHFFFAOYSA-N 0.000 description 2
- BWXFZQHCFYCUJE-UHFFFAOYSA-N 2-[4-[3-(3,4-dimethoxyphenyl)prop-2-enoylamino]phenoxy]acetic acid Chemical compound C1=C(OC)C(OC)=CC=C1C=CC(=O)NC1=CC=C(OCC(O)=O)C=C1 BWXFZQHCFYCUJE-UHFFFAOYSA-N 0.000 description 2
- MLGAECMFCGDQLR-UHFFFAOYSA-N 2-[4-[3-(4-hydroxyphenyl)prop-2-enoylamino]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1NC(=O)C=CC1=CC=C(O)C=C1 MLGAECMFCGDQLR-UHFFFAOYSA-N 0.000 description 2
- RRDFZVOQYJBJDT-UHFFFAOYSA-N 2-[4-[3-(4-hydroxyphenyl)prop-2-enoylamino]phenyl]acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1NC(=O)C=CC1=CC=C(O)C=C1 RRDFZVOQYJBJDT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BYHBHNKBISXCEP-UHFFFAOYSA-N 3-(4-acetyloxyphenyl)prop-2-enoic acid Chemical class CC(=O)OC1=CC=C(C=CC(O)=O)C=C1 BYHBHNKBISXCEP-UHFFFAOYSA-N 0.000 description 2
- QURCVMIEKCOAJU-UHFFFAOYSA-N 3-Hydroxy 4-Methoxy Cinnamic acid Chemical compound COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 2
- NOJXRHBIVBIMQY-UHFFFAOYSA-N 3-anilino-3-oxopropanoic acid Chemical class OC(=O)CC(=O)NC1=CC=CC=C1 NOJXRHBIVBIMQY-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 239000000043 antiallergic agent Substances 0.000 description 2
- 150000003934 aromatic aldehydes Chemical class 0.000 description 2
- 150000008430 aromatic amides Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 235000013985 cinnamic acid Nutrition 0.000 description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical class C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000001188 haloalkyl group Chemical group 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 150000007530 organic bases Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 2
- 229920000137 polyphosphoric acid Polymers 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 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
- MXOAEAUPQDYUQM-QMMMGPOBSA-N (S)-chlorphenesin Chemical compound OC[C@H](O)COC1=CC=C(Cl)C=C1 MXOAEAUPQDYUQM-QMMMGPOBSA-N 0.000 description 1
- HGDZRSNJGRIAKS-GQCTYLIASA-N (e)-3-(3,4-dimethoxyphenyl)prop-2-enoyl chloride Chemical compound COC1=CC=C(\C=C\C(Cl)=O)C=C1OC HGDZRSNJGRIAKS-GQCTYLIASA-N 0.000 description 1
- GMEKUFJCKPYDAH-UHFFFAOYSA-N 2-(3-phenylprop-2-enoylamino)benzoic acid Chemical class OC(=O)C1=CC=CC=C1NC(=O)C=CC1=CC=CC=C1 GMEKUFJCKPYDAH-UHFFFAOYSA-N 0.000 description 1
- GIFGMEWQGDEWKB-UHFFFAOYSA-N 2-(4-aminophenoxy)acetic acid Chemical compound NC1=CC=C(OCC(O)=O)C=C1 GIFGMEWQGDEWKB-UHFFFAOYSA-N 0.000 description 1
- HIFZPVZEBXWFCS-UHFFFAOYSA-N 2-[4-[3-(3-methoxy-4-propoxyphenyl)prop-2-enoylamino]phenyl]acetic acid Chemical compound C1=C(OC)C(OCCC)=CC=C1C=CC(=O)NC1=CC=C(CC(O)=O)C=C1 HIFZPVZEBXWFCS-UHFFFAOYSA-N 0.000 description 1
- RSTAYRVGFDRAMI-UHFFFAOYSA-N 2-amino-1-(diethylamino)ethanol Chemical compound CCN(CC)C(O)CN RSTAYRVGFDRAMI-UHFFFAOYSA-N 0.000 description 1
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 description 1
- KHMNCHDUSFCTGK-UHFFFAOYSA-N 2-aminophenylacetic acid Chemical compound NC1=CC=CC=C1CC(O)=O KHMNCHDUSFCTGK-UHFFFAOYSA-N 0.000 description 1
- ZCYXGVJUZBKJAI-UHFFFAOYSA-N 3,4,5-trimethoxydihydrocinnamic acid Chemical class COC1=CC(CCC(O)=O)=CC(OC)=C1OC ZCYXGVJUZBKJAI-UHFFFAOYSA-N 0.000 description 1
- MFFCZSWTQMCKFP-UHFFFAOYSA-N 3,5-dihydroxycinnamic acid Chemical class OC(=O)C=CC1=CC(O)=CC(O)=C1 MFFCZSWTQMCKFP-UHFFFAOYSA-N 0.000 description 1
- UIYJGLLTSVRSBM-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yl)propanoic acid Chemical compound OC(=O)CCC1=CC=C2OCOC2=C1 UIYJGLLTSVRSBM-UHFFFAOYSA-N 0.000 description 1
- ZGUOCBRYCRJZDR-UHFFFAOYSA-N 3-(2,4-diethylphenyl)prop-2-enoic acid Chemical compound CCC1=CC=C(C=CC(O)=O)C(CC)=C1 ZGUOCBRYCRJZDR-UHFFFAOYSA-N 0.000 description 1
- IRDSHCONNQHUFF-UHFFFAOYSA-N 3-(2,4-diethylphenyl)propanoic acid Chemical compound CCC1=CC=C(CCC(O)=O)C(CC)=C1 IRDSHCONNQHUFF-UHFFFAOYSA-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
- VEWUZPFHUFVIAJ-UHFFFAOYSA-N 3-(2-bromo-4-hydroxy-5-methoxyphenyl)propanoic acid Chemical compound COC1=CC(CCC(O)=O)=C(Br)C=C1O VEWUZPFHUFVIAJ-UHFFFAOYSA-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
- NHYJRLYFKZYPMO-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)propanoic acid Chemical class OC(=O)CCC1=CC=C(Cl)C(Cl)=C1 NHYJRLYFKZYPMO-UHFFFAOYSA-N 0.000 description 1
- FHEOAGCWJWUKJJ-UHFFFAOYSA-N 3-(3,4-dimethylphenyl)propanoic acid Chemical class CC1=CC=C(CCC(O)=O)C=C1C FHEOAGCWJWUKJJ-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
- BKKBVLIVEOBTMX-UHFFFAOYSA-N 3-(3,4-dipropoxyphenyl)propanoic acid Chemical class CCCOC1=CC=C(CCC(O)=O)C=C1OCCC BKKBVLIVEOBTMX-UHFFFAOYSA-N 0.000 description 1
- IGQGNLHKSKOMRI-UHFFFAOYSA-N 3-(3,5-diethoxyphenyl)prop-2-enoic acid Chemical compound CCOC1=CC(OCC)=CC(C=CC(O)=O)=C1 IGQGNLHKSKOMRI-UHFFFAOYSA-N 0.000 description 1
- ITPFIKQWNDGDLG-UHFFFAOYSA-N 3-(3,5-dihydroxyphenyl)propionic acid Chemical class OC(=O)CCC1=CC(O)=CC(O)=C1 ITPFIKQWNDGDLG-UHFFFAOYSA-N 0.000 description 1
- VLSRUFWCGBMYDJ-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)prop-2-enoic acid Chemical class COC1=CC(OC)=CC(C=CC(O)=O)=C1 VLSRUFWCGBMYDJ-UHFFFAOYSA-N 0.000 description 1
- LMBOJOXVLORKSQ-UHFFFAOYSA-N 3-(3,5-dimethoxyphenyl)propanoic acid Chemical class COC1=CC(CCC(O)=O)=CC(OC)=C1 LMBOJOXVLORKSQ-UHFFFAOYSA-N 0.000 description 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-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
- 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
- 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
- SXXZPHOCVWJAEN-UHFFFAOYSA-N 3-(3-methoxyphenyl)prop-2-enoyl chloride Chemical compound COC1=CC=CC(C=CC(Cl)=O)=C1 SXXZPHOCVWJAEN-UHFFFAOYSA-N 0.000 description 1
- CPDDDTNAMBSPRN-UHFFFAOYSA-N 3-(4-bromophenyl)prop-2-enoic acid Chemical class OC(=O)C=CC1=CC=C(Br)C=C1 CPDDDTNAMBSPRN-UHFFFAOYSA-N 0.000 description 1
- NCSTWHYWOVZDOC-UHFFFAOYSA-N 3-(4-bromophenyl)propanoic acid Chemical class OC(=O)CCC1=CC=C(Br)C=C1 NCSTWHYWOVZDOC-UHFFFAOYSA-N 0.000 description 1
- SONMBARPFYFEMC-UHFFFAOYSA-N 3-(4-butan-2-yloxyphenyl)prop-2-enoic acid Chemical class CCC(C)OC1=CC=C(C=CC(O)=O)C=C1 SONMBARPFYFEMC-UHFFFAOYSA-N 0.000 description 1
- AAHNIBROSVVFRO-UHFFFAOYSA-N 3-(4-butoxyphenyl)prop-2-enoic acid Chemical class CCCCOC1=CC=C(C=CC(O)=O)C=C1 AAHNIBROSVVFRO-UHFFFAOYSA-N 0.000 description 1
- ARXWPDDXBRKAIK-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-methylprop-2-enoyl chloride Chemical compound ClC(=O)C(C)=CC1=CC=C(Cl)C=C1 ARXWPDDXBRKAIK-UHFFFAOYSA-N 0.000 description 1
- GXLIFJYFGMHYDY-UHFFFAOYSA-N 3-(4-chlorophenyl)prop-2-enoic acid Chemical class OC(=O)C=CC1=CC=C(Cl)C=C1 GXLIFJYFGMHYDY-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
- DZLOUWYGNATKKZ-UHFFFAOYSA-N 3-(4-ethoxyphenyl)prop-2-enoic acid Chemical class CCOC1=CC=C(C=CC(O)=O)C=C1 DZLOUWYGNATKKZ-UHFFFAOYSA-N 0.000 description 1
- ZDSHOEQSCJOGCK-UHFFFAOYSA-N 3-(4-ethoxyphenyl)propanoic acid Chemical class CCOC1=CC=C(CCC(O)=O)C=C1 ZDSHOEQSCJOGCK-UHFFFAOYSA-N 0.000 description 1
- ISMMYAZSUSYVQG-UHFFFAOYSA-N 3-(4-fluorophenyl)prop-2-enoic acid Chemical class OC(=O)C=CC1=CC=C(F)C=C1 ISMMYAZSUSYVQG-UHFFFAOYSA-N 0.000 description 1
- ZMKXWDPUXLPHCA-UHFFFAOYSA-N 3-(4-fluorophenyl)propanoic acid Chemical class OC(=O)CCC1=CC=C(F)C=C1 ZMKXWDPUXLPHCA-UHFFFAOYSA-N 0.000 description 1
- FIUFLISGGHNPSM-UHFFFAOYSA-N 3-(4-methoxyphenyl)propanoic acid Chemical class COC1=CC=C(CCC(O)=O)C=C1 FIUFLISGGHNPSM-UHFFFAOYSA-N 0.000 description 1
- CSYAUJIRKNGPRT-UHFFFAOYSA-N 3-(4-propan-2-ylphenyl)propanoic acid Chemical compound CC(C)C1=CC=C(CCC(O)=O)C=C1 CSYAUJIRKNGPRT-UHFFFAOYSA-N 0.000 description 1
- WTYNDSOJMSGRQV-UHFFFAOYSA-N 3-(4-propoxyphenyl)prop-2-enoic acid Chemical class CCCOC1=CC=C(C=CC(O)=O)C=C1 WTYNDSOJMSGRQV-UHFFFAOYSA-N 0.000 description 1
- WRBXYOSHIVEUNT-UHFFFAOYSA-N 3-(4-propylphenyl)propanoic acid Chemical class CCCC1=CC=C(CCC(O)=O)C=C1 WRBXYOSHIVEUNT-UHFFFAOYSA-N 0.000 description 1
- LDYGRLNSOKABMM-UHFFFAOYSA-N 3-(p-tolyl)propionic acid Chemical class CC1=CC=C(CCC(O)=O)C=C1 LDYGRLNSOKABMM-UHFFFAOYSA-N 0.000 description 1
- NZUIHGSLMBYAMW-UHFFFAOYSA-N 3-[4-(2-methylpropoxy)phenyl]prop-2-enoic acid Chemical class CC(C)COC1=CC=C(C=CC(O)=O)C=C1 NZUIHGSLMBYAMW-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
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical class CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 1
- 208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 1
- RZZPDXZPRHQOCG-OJAKKHQRSA-O CDP-choline(1+) Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OCC[N+](C)(C)C)O[C@H]1N1C(=O)N=C(N)C=C1 RZZPDXZPRHQOCG-OJAKKHQRSA-O 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 208000024780 Urticaria Diseases 0.000 description 1
- FXTAOSIHTREOSA-UHFFFAOYSA-N [4-(3-chloro-3-oxoprop-1-enyl)phenyl] acetate Chemical compound CC(=O)OC1=CC=C(C=CC(Cl)=O)C=C1 FXTAOSIHTREOSA-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
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005157 alkyl carboxy group Chemical group 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 208000030961 allergic reaction Diseases 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229960003993 chlorphenesin Drugs 0.000 description 1
- APEJMQOBVMLION-UHFFFAOYSA-N cinnamamide Chemical class NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 description 1
- IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 description 1
- 150000004292 cyclic ethers Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-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
- HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- IBGBOGKPIMZRRU-UHFFFAOYSA-N ethyl 2-(4-aminophenoxy)acetate Chemical compound CCOC(=O)COC1=CC=C(N)C=C1 IBGBOGKPIMZRRU-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
- 229960003699 evans blue Drugs 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 1
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- LUSQADYGIDUVOH-UHFFFAOYSA-N n-(4-hydroxyphenyl)-3-(4-methylphenyl)prop-2-enamide Chemical compound C1=CC(C)=CC=C1C=CC(=O)NC1=CC=C(O)C=C1 LUSQADYGIDUVOH-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical class OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000004672 propanoic acids Chemical class 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- QYKUKWGTVZDOGM-UHFFFAOYSA-M sodium;2-(2-aminophenyl)propanoate Chemical compound [Na+].[O-]C(=O)C(C)C1=CC=CC=C1N QYKUKWGTVZDOGM-UHFFFAOYSA-M 0.000 description 1
- HMTQUXLLFLKDDP-UHFFFAOYSA-M sodium;2-[2-[3-(3-methoxyphenyl)prop-2-enoylamino]phenyl]propanoate Chemical compound [Na+].COC1=CC=CC(C=CC(=O)NC=2C(=CC=CC=2)C(C)C([O-])=O)=C1 HMTQUXLLFLKDDP-UHFFFAOYSA-M 0.000 description 1
- BMJXWIVZCONCJO-UHFFFAOYSA-M sodium;2-[2-[3-(4-methylphenyl)propanoylamino]phenyl]acetate Chemical compound [Na+].C1=CC(C)=CC=C1CCC(=O)NC1=CC=CC=C1CC([O-])=O BMJXWIVZCONCJO-UHFFFAOYSA-M 0.000 description 1
- FNFKDKOXIQGRKJ-UHFFFAOYSA-M sodium;2-[3-[[3-(4-chlorophenyl)-2-methylprop-2-enoyl]amino]phenyl]acetate Chemical compound [Na+].C=1C=CC(CC([O-])=O)=CC=1NC(=O)C(C)=CC1=CC=C(Cl)C=C1 FNFKDKOXIQGRKJ-UHFFFAOYSA-M 0.000 description 1
- OTIGQPFFXQWVQS-UHFFFAOYSA-M sodium;2-[4-[3-(4-hydroxyphenyl)prop-2-enoylamino]phenyl]acetate Chemical compound [Na+].C1=CC(O)=CC=C1C=CC(=O)NC1=CC=C(CC([O-])=O)C=C1 OTIGQPFFXQWVQS-UHFFFAOYSA-M 0.000 description 1
- WPTJBFNYRRZIDZ-UHFFFAOYSA-M sodium;2-phenoxyacetate Chemical compound [Na+].[O-]C(=O)COC1=CC=CC=C1 WPTJBFNYRRZIDZ-UHFFFAOYSA-M 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4367574A JPS5632981B2 (enrdf_load_stackoverflow) | 1974-04-18 | 1974-04-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE828003A true BE828003A (fr) | 1975-08-18 |
Family
ID=12670403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE155462A BE828003A (fr) | 1974-04-18 | 1975-04-16 | Nouveaux derives d'acides amidocarboxyliques aromatiques |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5632981B2 (enrdf_load_stackoverflow) |
| BE (1) | BE828003A (enrdf_load_stackoverflow) |
| ZA (1) | ZA752375B (enrdf_load_stackoverflow) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6097946A (ja) * | 1983-11-01 | 1985-05-31 | Ono Pharmaceut Co Ltd | カルボキサミド誘導体 |
| JPS60116657A (ja) * | 1983-11-30 | 1985-06-24 | Ono Pharmaceut Co Ltd | アニリン誘導体 |
| JPS60142936A (ja) * | 1983-12-28 | 1985-07-29 | Ono Pharmaceut Co Ltd | 置換フエニル誘導体 |
| 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 |
| JPS61126061A (ja) * | 1984-11-22 | 1986-06-13 | Ono Pharmaceut Co Ltd | アリールカルバモイル化合物 |
-
1974
- 1974-04-18 JP JP4367574A patent/JPS5632981B2/ja not_active Expired
-
1975
- 1975-04-15 ZA ZA00752375A patent/ZA752375B/xx unknown
- 1975-04-16 BE BE155462A patent/BE828003A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS511438A (enrdf_load_stackoverflow) | 1976-01-08 |
| ZA752375B (en) | 1976-04-28 |
| JPS5632981B2 (enrdf_load_stackoverflow) | 1981-07-31 |
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