DE2810253A1 - Neue chalkonderivate und verfahren zu ihrer herstellung - Google Patents
Neue chalkonderivate und verfahren zu ihrer herstellungInfo
- Publication number
- DE2810253A1 DE2810253A1 DE19782810253 DE2810253A DE2810253A1 DE 2810253 A1 DE2810253 A1 DE 2810253A1 DE 19782810253 DE19782810253 DE 19782810253 DE 2810253 A DE2810253 A DE 2810253A DE 2810253 A1 DE2810253 A1 DE 2810253A1
- Authority
- DE
- Germany
- Prior art keywords
- carboxy
- carboxymethoxy
- methanol
- solution
- product
- 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.)
- Granted
Links
- 238000000034 method Methods 0.000 title claims description 8
- 239000007787 solid Substances 0.000 claims description 67
- 150000001875 compounds Chemical class 0.000 claims description 22
- 238000002360 preparation method Methods 0.000 claims description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
- -1 carboxymethoxy Chemical group 0.000 claims description 9
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 8
- DQFBYFPFKXHELB-UHFFFAOYSA-N Chalcone Natural products C=1C=CC=CC=1C(=O)C=CC1=CC=CC=C1 DQFBYFPFKXHELB-UHFFFAOYSA-N 0.000 claims description 7
- 235000005513 chalcones Nutrition 0.000 claims description 7
- DQFBYFPFKXHELB-VAWYXSNFSA-N trans-chalcone Chemical compound C=1C=CC=CC=1C(=O)\C=C\C1=CC=CC=C1 DQFBYFPFKXHELB-VAWYXSNFSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000005111 carboxyalkoxy group Chemical group 0.000 claims description 5
- 239000007788 liquid Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 238000009833 condensation Methods 0.000 claims description 4
- 230000005494 condensation Effects 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- BYZMEFUINJBANB-UHFFFAOYSA-N 2-[3-[4-(carboxymethoxy)phenyl]-3-oxoprop-1-enyl]benzoic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1C(=O)C=CC1=CC=CC=C1C(O)=O BYZMEFUINJBANB-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000008062 acetophenones Chemical class 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 150000007530 organic bases Chemical class 0.000 claims description 2
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 2
- IPCDYHILYJQPGX-UHFFFAOYSA-N 2-[4-[3-(4-sulfophenyl)prop-2-enoyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1C(=O)C=CC1=CC=C(S(O)(=O)=O)C=C1 IPCDYHILYJQPGX-UHFFFAOYSA-N 0.000 claims 1
- BLPZTWKLVIIQHM-UHFFFAOYSA-N 3-[3-[4-(carboxymethoxy)phenyl]-3-oxoprop-1-enyl]benzoic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1C(=O)C=CC1=CC=CC(C(O)=O)=C1 BLPZTWKLVIIQHM-UHFFFAOYSA-N 0.000 claims 1
- PWYRSFSDHFTVOH-UHFFFAOYSA-N 4-[3-[4-(carboxymethoxy)-3-methoxyphenyl]-3-oxoprop-1-enyl]benzoic acid Chemical compound C1=C(OCC(O)=O)C(OC)=CC(C(=O)C=CC=2C=CC(=CC=2)C(O)=O)=C1 PWYRSFSDHFTVOH-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- CBRXPQSYMMCZLR-UHFFFAOYSA-N OC1=C(C=CC=C1OC)C=CC(=O)C1=CC=C(C=C1)OCC(=O)O Chemical compound OC1=C(C=CC=C1OC)C=CC(=O)C1=CC=C(C=C1)OCC(=O)O CBRXPQSYMMCZLR-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 237
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 135
- 239000000243 solution Substances 0.000 description 109
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 96
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 83
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
- 238000004809 thin layer chromatography Methods 0.000 description 68
- 239000011541 reaction mixture Substances 0.000 description 58
- 239000000047 product Substances 0.000 description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- 239000000463 material Substances 0.000 description 42
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 28
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 27
- 238000002844 melting Methods 0.000 description 25
- 230000008018 melting Effects 0.000 description 25
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- GOUHYARYYWKXHS-UHFFFAOYSA-N 4-formylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=O)C=C1 GOUHYARYYWKXHS-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 238000002425 crystallisation Methods 0.000 description 14
- 230000008025 crystallization Effects 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- 239000012153 distilled water Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 238000001914 filtration Methods 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000003208 petroleum Substances 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 6
- 229940106681 chloroacetic acid Drugs 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 239000012535 impurity Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 229940073735 4-hydroxy acetophenone Drugs 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000001556 precipitation Methods 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- OYNIIKHNXNPSAG-UHFFFAOYSA-N 2-(4-formylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=C(C=O)C=C1 OYNIIKHNXNPSAG-UHFFFAOYSA-N 0.000 description 4
- 150000001788 chalcone derivatives Chemical class 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 239000005457 ice water Substances 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 238000000354 decomposition reaction Methods 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 238000003760 magnetic stirring Methods 0.000 description 3
- UVSBCUAQEZINCQ-UHFFFAOYSA-N methyl 3-formylbenzoate Chemical compound COC(=O)C1=CC=CC(C=O)=C1 UVSBCUAQEZINCQ-UHFFFAOYSA-N 0.000 description 3
- 239000012452 mother liquor Substances 0.000 description 3
- 230000020477 pH reduction Effects 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- GSWTXZXGONEVJC-UHFFFAOYSA-N 1-(3-fluoro-4-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC=C(O)C(F)=C1 GSWTXZXGONEVJC-UHFFFAOYSA-N 0.000 description 2
- PKZJLOCLABXVMC-UHFFFAOYSA-N 2-Methoxybenzaldehyde Chemical compound COC1=CC=CC=C1C=O PKZJLOCLABXVMC-UHFFFAOYSA-N 0.000 description 2
- SIMKBYSULJHOMR-UHFFFAOYSA-N 2-[4-[3-[4-(hydroxymethyl)phenyl]prop-2-enoyl]phenoxy]acetic acid Chemical compound C1=CC(CO)=CC=C1C=CC(=O)C1=CC=C(OCC(O)=O)C=C1 SIMKBYSULJHOMR-UHFFFAOYSA-N 0.000 description 2
- MWSBXHPHUZMQRC-UHFFFAOYSA-N 3-(3-methoxycarbonylphenyl)pentanedioic acid Chemical compound COC(=O)C1=CC=CC(C(CC(O)=O)CC(O)=O)=C1 MWSBXHPHUZMQRC-UHFFFAOYSA-N 0.000 description 2
- JMAZIJYBOSJVNT-UHFFFAOYSA-N 3-[3-(4-hydroxyphenyl)-3-oxoprop-1-enyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(C=CC(=O)C=2C=CC(O)=CC=2)=C1 JMAZIJYBOSJVNT-UHFFFAOYSA-N 0.000 description 2
- LUJMEECXHPYQOF-UHFFFAOYSA-N 3-hydroxyacetophenone Chemical compound CC(=O)C1=CC=CC(O)=C1 LUJMEECXHPYQOF-UHFFFAOYSA-N 0.000 description 2
- IAVREABSGIHHMO-UHFFFAOYSA-N 3-hydroxybenzaldehyde Chemical compound OC1=CC=CC(C=O)=C1 IAVREABSGIHHMO-UHFFFAOYSA-N 0.000 description 2
- WMPDAIZRQDCGFH-UHFFFAOYSA-N 3-methoxybenzaldehyde Chemical compound COC1=CC=CC(C=O)=C1 WMPDAIZRQDCGFH-UHFFFAOYSA-N 0.000 description 2
- QBHDSQZASIBAAI-UHFFFAOYSA-N 4-acetylbenzoic acid Chemical compound CC(=O)C1=CC=C(C(O)=O)C=C1 QBHDSQZASIBAAI-UHFFFAOYSA-N 0.000 description 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 229940117975 chromium trioxide Drugs 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000001030 gas--liquid chromatography Methods 0.000 description 2
- GPSDUZXPYCFOSQ-UHFFFAOYSA-N m-toluic acid Chemical compound CC1=CC=CC(C(O)=O)=C1 GPSDUZXPYCFOSQ-UHFFFAOYSA-N 0.000 description 2
- CPXCDEMFNPKOEF-UHFFFAOYSA-N methyl 3-methylbenzoate Chemical compound COC(=O)C1=CC=CC(C)=C1 CPXCDEMFNPKOEF-UHFFFAOYSA-N 0.000 description 2
- JUYVXCGKMCYNBN-UHFFFAOYSA-N methyl 4-hydroxybutanoate Chemical group COC(=O)CCCO JUYVXCGKMCYNBN-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- ZRSNZINYAWTAHE-UHFFFAOYSA-N p-methoxybenzaldehyde Chemical compound COC1=CC=C(C=O)C=C1 ZRSNZINYAWTAHE-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000011343 solid material Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000375 suspending agent Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- LQASUDVYVOFKNK-UHFFFAOYSA-N 1-(3-fluoro-4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(C)=O)C=C1F LQASUDVYVOFKNK-UHFFFAOYSA-N 0.000 description 1
- KHBBQMHTRDEPCR-UHFFFAOYSA-N 2-(3-formylphenoxy)acetic acid Chemical compound OC(=O)COC1=CC=CC(C=O)=C1 KHBBQMHTRDEPCR-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- BZUQCRZTLNCSEE-UHFFFAOYSA-N 2-[4-[3-(3-methoxyphenyl)prop-2-enoyl]phenoxy]acetic acid Chemical compound COC1=CC=CC(C=CC(=O)C=2C=CC(OCC(O)=O)=CC=2)=C1 BZUQCRZTLNCSEE-UHFFFAOYSA-N 0.000 description 1
- UZVWWRUBQJZHPL-UHFFFAOYSA-N 2-[4-[3-(3-methylphenyl)prop-2-enoyl]phenoxy]acetic acid Chemical compound CC1=CC=CC(C=CC(=O)C=2C=CC(OCC(O)=O)=CC=2)=C1 UZVWWRUBQJZHPL-UHFFFAOYSA-N 0.000 description 1
- DSJYBJQBVDEKDW-UHFFFAOYSA-N 2-[4-[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]phenoxy]acetic acid;sodium Chemical compound [Na].C1=C(O)C(OC)=CC(C=CC(=O)C=2C=CC(OCC(O)=O)=CC=2)=C1 DSJYBJQBVDEKDW-UHFFFAOYSA-N 0.000 description 1
- LGWGLTSMPGQZON-UHFFFAOYSA-N 2-[4-[3-(4-methoxyphenyl)prop-2-enoyl]phenoxy]acetic acid;sodium Chemical compound [Na].C1=CC(OC)=CC=C1C=CC(=O)C1=CC=C(OCC(O)=O)C=C1 LGWGLTSMPGQZON-UHFFFAOYSA-N 0.000 description 1
- HYOAPBYBPFLBRA-UHFFFAOYSA-N 2-[4-[3-(4-methylphenyl)prop-2-enoyl]phenoxy]acetic acid Chemical compound C1=CC(C)=CC=C1C=CC(=O)C1=CC=C(OCC(O)=O)C=C1 HYOAPBYBPFLBRA-UHFFFAOYSA-N 0.000 description 1
- JATPGTOTNVAZRJ-UHFFFAOYSA-N 2-[4-[3-[3-(carboxymethoxy)phenyl]prop-2-enoyl]phenoxy]acetic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1C(=O)C=CC1=CC=CC(OCC(O)=O)=C1 JATPGTOTNVAZRJ-UHFFFAOYSA-N 0.000 description 1
- DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 1
- HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
- PXPZIMHJMBPTHK-UHFFFAOYSA-N 2-phenacyloxyacetic acid Chemical compound OC(=O)COCC(=O)C1=CC=CC=C1 PXPZIMHJMBPTHK-UHFFFAOYSA-N 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- KXNXFGGNSPCWCR-UHFFFAOYSA-N 4-[3-(3-fluoro-4-hydroxyphenyl)-3-oxoprop-1-enyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C=CC(=O)C1=CC=C(O)C(F)=C1 KXNXFGGNSPCWCR-UHFFFAOYSA-N 0.000 description 1
- RHOTYTPYWLMIJA-UHFFFAOYSA-N 4-[3-[3-(carboxymethoxy)phenyl]-3-oxoprop-1-enyl]benzoic acid Chemical compound OC(=O)COC1=CC=CC(C(=O)C=CC=2C=CC(=CC=2)C(O)=O)=C1 RHOTYTPYWLMIJA-UHFFFAOYSA-N 0.000 description 1
- ZEKLXOOLTGNIDC-UHFFFAOYSA-N 4-[3-[4-(carboxymethoxy)-3-fluorophenyl]-3-oxoprop-1-enyl]benzoic acid Chemical compound C1=C(F)C(OCC(=O)O)=CC=C1C(=O)C=CC1=CC=C(C(O)=O)C=C1 ZEKLXOOLTGNIDC-UHFFFAOYSA-N 0.000 description 1
- HXSSCTOWBWPFEV-UHFFFAOYSA-N 4-[3-[4-(carboxymethoxy)phenyl]-3-oxoprop-1-enyl]benzoic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1C(=O)C=CC1=CC=C(C(O)=O)C=C1 HXSSCTOWBWPFEV-UHFFFAOYSA-N 0.000 description 1
- UDDLLGLQYKHDLW-UHFFFAOYSA-N 4-[3-[4-(carboxymethoxy)phenyl]prop-2-enoyl]benzoic acid Chemical compound C1=CC(OCC(=O)O)=CC=C1C=CC(=O)C1=CC=C(C(O)=O)C=C1 UDDLLGLQYKHDLW-UHFFFAOYSA-N 0.000 description 1
- IXPGMTPGNMUMER-UHFFFAOYSA-N 4-[3-[4-(carboxymethoxy)phenyl]prop-2-enoyl]benzoic acid;sodium Chemical compound [Na].[Na].C1=CC(OCC(=O)O)=CC=C1C=CC(=O)C1=CC=C(C(O)=O)C=C1 IXPGMTPGNMUMER-UHFFFAOYSA-N 0.000 description 1
- UWDMKTDPDJCJOP-UHFFFAOYSA-N 4-hydroxy-2,2,6,6-tetramethylpiperidin-1-ium-4-carboxylate Chemical compound CC1(C)CC(O)(C(O)=O)CC(C)(C)N1 UWDMKTDPDJCJOP-UHFFFAOYSA-N 0.000 description 1
- 206010027654 Allergic conditions Diseases 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
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
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- 108010010803 Gelatin Proteins 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
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- 208000025865 Ulcer Diseases 0.000 description 1
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-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
- 239000011149 active material Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 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
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical compound COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 description 1
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- 235000019568 aromas Nutrition 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- VIQSRHWJEKERKR-UHFFFAOYSA-L disodium;terephthalate Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 VIQSRHWJEKERKR-UHFFFAOYSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- VRZVPALEJCLXPR-UHFFFAOYSA-N ethyl 4-methylbenzenesulfonate Chemical compound CCOS(=O)(=O)C1=CC=C(C)C=C1 VRZVPALEJCLXPR-UHFFFAOYSA-N 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 239000010408 film Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 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
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 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
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 238000007273 lactonization reaction Methods 0.000 description 1
- 229940080428 lactose 200 mg Drugs 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- OVWYEQOVUDKZNU-UHFFFAOYSA-N m-tolualdehyde Chemical compound CC1=CC=CC(C=O)=C1 OVWYEQOVUDKZNU-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- FEIOASZZURHTHB-UHFFFAOYSA-N methyl 4-formylbenzoate Chemical compound COC(=O)C1=CC=C(C=O)C=C1 FEIOASZZURHTHB-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
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- 239000008188 pellet Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- XYGBKMMCQDZQOZ-UHFFFAOYSA-M sodium;4-hydroxybutanoate Chemical compound [Na+].OCCCC([O-])=O XYGBKMMCQDZQOZ-UHFFFAOYSA-M 0.000 description 1
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- 239000012265 solid product Substances 0.000 description 1
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- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
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- 229940014800 succinic anhydride Drugs 0.000 description 1
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- 235000020357 syrup Nutrition 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
- C07C45/29—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C47/00—Compounds having —CHO groups
- C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
- C07C47/56—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing hydroxy groups
-
- 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
- C07C59/74—Unsaturated compounds containing —CHO groups
-
- 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
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/38—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups having unsaturation outside the aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
- C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/582—Recycling of unreacted starting or intermediate materials
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (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)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3592577 | 1977-08-26 | ||
| GB11339/77A GB1566497A (en) | 1977-08-26 | 1978-03-10 | Chalcone derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2810253A1 true DE2810253A1 (de) | 1978-09-21 |
| DE2810253C2 DE2810253C2 (enExample) | 1989-01-26 |
Family
ID=26248208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19782810253 Granted DE2810253A1 (de) | 1977-08-26 | 1978-03-09 | Neue chalkonderivate und verfahren zu ihrer herstellung |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4190671A (enExample) |
| JP (1) | JPS53116356A (enExample) |
| AU (1) | AU520288B2 (enExample) |
| DE (1) | DE2810253A1 (enExample) |
| ES (1) | ES467961A1 (enExample) |
| FR (1) | FR2383157B1 (enExample) |
| GB (1) | GB1566497A (enExample) |
| IT (1) | IT1113112B (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987005215A1 (fr) * | 1986-03-08 | 1987-09-11 | Dainippon Ink And Chemicals, Inc. | Agent anti-allergique |
| AU601992B2 (en) * | 1986-06-21 | 1990-09-27 | Dainippon Ink And Chemicals Inc. | Isoliquiritigenin for the treatment of kidney and liver diseases |
Families Citing this family (65)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4256760A (en) * | 1979-01-09 | 1981-03-17 | Laboratorios Bago S.A. | Methods of treating mammals suffering from inflammation and pain |
| FR2492815A1 (fr) * | 1980-10-23 | 1982-04-30 | Sori Soc Rech Ind | Nouveau derive d'acide cinnamoyl-cinnamique, son procede de preparation et son application en therapeutique |
| US4760161A (en) * | 1983-04-25 | 1988-07-26 | Merck & Co., Inc. | Ipoxygenase inhibitors |
| US4733002A (en) * | 1984-05-23 | 1988-03-22 | Green Cross Corporation | Lipoxygenase inhibitor |
| EP0170105B1 (en) * | 1984-07-07 | 1990-10-17 | Koichi Prof. Dr. Shudo | Benzoic acid derivatives |
| GB8426424D0 (en) * | 1984-10-19 | 1984-11-28 | Biorex Laboratories Ltd | Chalcone derivatives |
| HU198292B (en) * | 1987-09-25 | 1989-09-28 | Richter Gedeon Vegyeszet | Process for producing salicilates and pharmaceutical compositions comprising such active ingredient |
| EP0502205A4 (en) * | 1990-09-21 | 1992-11-25 | Nippon Hypox Laboratories Incorporated | Chalcone derivative and ultraviolet screening cosmetic |
| FR2676439B1 (fr) * | 1991-05-13 | 1994-10-28 | Cird Galderma | Nouveaux composes bi-aromatiques derives d'un motif salicylique, leur procede de preparation et leur utilisation en medecine humaine et veterinaire ainsi qu'en cosmetique. |
| US5773182A (en) | 1993-08-05 | 1998-06-30 | Kimberly-Clark Worldwide, Inc. | Method of light stabilizing a colorant |
| US5733693A (en) | 1993-08-05 | 1998-03-31 | Kimberly-Clark Worldwide, Inc. | Method for improving the readability of data processing forms |
| US5681380A (en) | 1995-06-05 | 1997-10-28 | Kimberly-Clark Worldwide, Inc. | Ink for ink jet printers |
| US6017661A (en) | 1994-11-09 | 2000-01-25 | Kimberly-Clark Corporation | Temporary marking using photoerasable colorants |
| US5645964A (en) | 1993-08-05 | 1997-07-08 | Kimberly-Clark Corporation | Digital information recording media and method of using same |
| US6017471A (en) | 1993-08-05 | 2000-01-25 | Kimberly-Clark Worldwide, Inc. | Colorants and colorant modifiers |
| US5865471A (en) | 1993-08-05 | 1999-02-02 | Kimberly-Clark Worldwide, Inc. | Photo-erasable data processing forms |
| US6211383B1 (en) | 1993-08-05 | 2001-04-03 | Kimberly-Clark Worldwide, Inc. | Nohr-McDonald elimination reaction |
| US6242057B1 (en) | 1994-06-30 | 2001-06-05 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition and applications therefor |
| US6071979A (en) | 1994-06-30 | 2000-06-06 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition method of generating a reactive species and applications therefor |
| US5685754A (en) | 1994-06-30 | 1997-11-11 | Kimberly-Clark Corporation | Method of generating a reactive species and polymer coating applications therefor |
| US6008268A (en) | 1994-10-21 | 1999-12-28 | Kimberly-Clark Worldwide, Inc. | Photoreactor composition, method of generating a reactive species, and applications therefor |
| US5786132A (en) | 1995-06-05 | 1998-07-28 | Kimberly-Clark Corporation | Pre-dyes, mutable dye compositions, and methods of developing a color |
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| US3255241A (en) * | 1961-01-19 | 1966-06-07 | Merck & Co Inc | (2-alkylidene acyl)phenoxy-and (2-alkylidene acyl)phenylmercaptocarboxylic acids |
| US3928421A (en) * | 1973-10-30 | 1975-12-23 | Taisho Pharmaceutical Co Ltd | Anti-gastric ulcer chalcone ethers |
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| HU163394B (enExample) * | 1971-12-20 | 1973-08-28 | ||
| JPS5170815A (ja) * | 1974-12-12 | 1976-06-18 | Mitsubishi Petrochemical Co | Josozai |
| US3994955A (en) * | 1975-01-20 | 1976-11-30 | G. D. Searle & Co. | Substituted phenoxydialkylacetic acids and esters |
| JPS5297950A (en) * | 1976-02-13 | 1977-08-17 | Taisho Pharmaceut Co Ltd | Chalconeether derivatives |
-
1978
- 1978-03-03 US US05/883,252 patent/US4190671A/en not_active Expired - Lifetime
- 1978-03-06 FR FR7806279A patent/FR2383157B1/fr not_active Expired
- 1978-03-09 DE DE19782810253 patent/DE2810253A1/de active Granted
- 1978-03-10 GB GB11339/77A patent/GB1566497A/en not_active Expired
- 1978-03-13 IT IT7821146A patent/IT1113112B/it active
- 1978-03-15 JP JP3049378A patent/JPS53116356A/ja active Granted
- 1978-03-17 ES ES78467961A patent/ES467961A1/es not_active Expired
- 1978-03-29 AU AU34552/78A patent/AU520288B2/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3255241A (en) * | 1961-01-19 | 1966-06-07 | Merck & Co Inc | (2-alkylidene acyl)phenoxy-and (2-alkylidene acyl)phenylmercaptocarboxylic acids |
| US3928421A (en) * | 1973-10-30 | 1975-12-23 | Taisho Pharmaceutical Co Ltd | Anti-gastric ulcer chalcone ethers |
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| Title |
|---|
| Bull. Soc. Chim. Belg. 66, 1957, S.619-628 * |
| LIEBIG: Ann. Chem. 460, 1928, S.147 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1987005215A1 (fr) * | 1986-03-08 | 1987-09-11 | Dainippon Ink And Chemicals, Inc. | Agent anti-allergique |
| US4952564A (en) * | 1986-03-08 | 1990-08-28 | Dainippon Ink And Chemicals, Inc. | Antiallergic agent |
| AU601992B2 (en) * | 1986-06-21 | 1990-09-27 | Dainippon Ink And Chemicals Inc. | Isoliquiritigenin for the treatment of kidney and liver diseases |
Also Published As
| Publication number | Publication date |
|---|---|
| IT7821146A0 (it) | 1978-03-13 |
| DE2810253C2 (enExample) | 1989-01-26 |
| IT1113112B (it) | 1986-01-20 |
| US4190671A (en) | 1980-02-26 |
| JPS53116356A (en) | 1978-10-11 |
| JPS641456B2 (enExample) | 1989-01-11 |
| FR2383157A1 (fr) | 1978-10-06 |
| AU3455278A (en) | 1979-10-04 |
| GB1566497A (en) | 1980-04-30 |
| ES467961A1 (es) | 1979-09-01 |
| FR2383157B1 (fr) | 1983-03-25 |
| AU520288B2 (en) | 1982-01-21 |
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