FR2481118A1 - Application a titre de medicaments de derives substitues de l'acide phenyl-4-oxo-2-butenoique - Google Patents
Application a titre de medicaments de derives substitues de l'acide phenyl-4-oxo-2-butenoique Download PDFInfo
- Publication number
- FR2481118A1 FR2481118A1 FR8009216A FR8009216A FR2481118A1 FR 2481118 A1 FR2481118 A1 FR 2481118A1 FR 8009216 A FR8009216 A FR 8009216A FR 8009216 A FR8009216 A FR 8009216A FR 2481118 A1 FR2481118 A1 FR 2481118A1
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- FR
- France
- Prior art keywords
- alkaline
- formula
- products
- medicaments
- hydrogen atom
- 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
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- 239000003814 drug Substances 0.000 title claims abstract description 31
- CVFDZUVFEOTCQK-UHFFFAOYSA-N 4-oxo-2-phenylbut-2-enoic acid Chemical group C(=O)C=C(C(=O)O)C1=CC=CC=C1 CVFDZUVFEOTCQK-UHFFFAOYSA-N 0.000 title 1
- 150000001412 amines Chemical class 0.000 claims abstract description 14
- 150000003254 radicals Chemical class 0.000 claims abstract description 8
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical group F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- BLNWTAHYTCHDJH-UHFFFAOYSA-O hydroxy(oxo)azanium Chemical compound O[NH+]=O BLNWTAHYTCHDJH-UHFFFAOYSA-O 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 3
- -1 alkyl radical Chemical group 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 4
- PBLUZBCDLSSYAR-AATRIKPKSA-N (e)-4-(2-nitrophenyl)-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)C1=CC=CC=C1[N+]([O-])=O PBLUZBCDLSSYAR-AATRIKPKSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 230000000767 anti-ulcer Effects 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052731 fluorine Chemical group 0.000 claims description 3
- 159000000011 group IA salts Chemical class 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
- 229940126601 medicinal product Drugs 0.000 claims 2
- ZOIRMVZWDRLJPI-OWOJBTEDSA-N (e)-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C\C=O ZOIRMVZWDRLJPI-OWOJBTEDSA-N 0.000 claims 1
- 229940124599 anti-inflammatory drug Drugs 0.000 claims 1
- 238000002483 medication Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical group [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 239000000047 product Substances 0.000 description 38
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 10
- 238000000034 method Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 210000002784 stomach Anatomy 0.000 description 6
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- IQZLUWLMQNGTIW-UHFFFAOYSA-N acetoveratrone Chemical compound COC1=CC=C(C(C)=O)C=C1OC IQZLUWLMQNGTIW-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 230000002496 gastric effect Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 208000025865 Ulcer Diseases 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000004452 microanalysis Methods 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 239000012429 reaction media Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 238000005292 vacuum distillation Methods 0.000 description 3
- XIZWELOARFUPLO-ONEGZZNKSA-N (e)-4-(3,4-dichlorophenyl)-4-oxobut-2-enoic acid Chemical group OC(=O)\C=C\C(=O)C1=CC=C(Cl)C(Cl)=C1 XIZWELOARFUPLO-ONEGZZNKSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical group CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- 206010020601 Hyperchlorhydria Diseases 0.000 description 2
- 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 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- 239000004480 active ingredient Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000003699 antiulcer agent Substances 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 230000001079 digestive effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 210000001187 pylorus Anatomy 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000036269 ulceration Effects 0.000 description 2
- QUWWWXPLUJFEHM-GQCTYLIASA-N (e)-4-(3,4-dimethoxyphenyl)-4-oxobut-2-enoic acid Chemical compound COC1=CC=C(C(=O)\C=C\C(O)=O)C=C1OC QUWWWXPLUJFEHM-GQCTYLIASA-N 0.000 description 1
- CMSWGWOQRTZZAS-AATRIKPKSA-N (e)-4-(4-fluorophenyl)-4-oxobut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)C1=CC=C(F)C=C1 CMSWGWOQRTZZAS-AATRIKPKSA-N 0.000 description 1
- PLPDHGOODMBBGN-VOTSOKGWSA-N (e)-4-oxo-4-phenylbut-2-enoic acid Chemical compound OC(=O)\C=C\C(=O)C1=CC=CC=C1 PLPDHGOODMBBGN-VOTSOKGWSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- LNBMZFHIYRDKNS-UHFFFAOYSA-N 2,2-dimethoxy-1-phenylethanone Chemical compound COC(OC)C(=O)C1=CC=CC=C1 LNBMZFHIYRDKNS-UHFFFAOYSA-N 0.000 description 1
- RVVAEJKFWAAGKL-UHFFFAOYSA-N 4-(4-fluorophenyl)-2-hydroxy-4-oxobutanoic acid Chemical compound OC(=O)C(O)CC(=O)C1=CC=C(F)C=C1 RVVAEJKFWAAGKL-UHFFFAOYSA-N 0.000 description 1
- DJJGRVVIVRCHRI-UHFFFAOYSA-N 4-hydroxy-1-phenylbut-2-en-1-one Chemical compound OCC=CC(=O)C1=CC=CC=C1 DJJGRVVIVRCHRI-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 229910002012 Aerosil® Inorganic materials 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-DYCDLGHISA-N Deuterium chloride Chemical compound [2H]Cl VEXZGXHMUGYJMC-DYCDLGHISA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 208000034991 Hiatal Hernia Diseases 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
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000001632 acidimetric titration Methods 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000001539 anorectic effect Effects 0.000 description 1
- 230000002924 anti-infective effect Effects 0.000 description 1
- 230000001262 anti-secretory effect Effects 0.000 description 1
- 239000008135 aqueous vehicle Substances 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
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 210000002318 cardia Anatomy 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 210000001198 duodenum Anatomy 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- VMSUNVQFEYKKMB-UHFFFAOYSA-N ethanamine;methanamine Chemical compound NC.CCN VMSUNVQFEYKKMB-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000000762 glandular Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000003387 muscular Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 229940100486 rice starch Drugs 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
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 210000001562 sternum Anatomy 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- 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
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional 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
- C07C59/88—Unsaturated compounds containing keto groups containing halogen
-
- 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
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- Medicinal Chemistry (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8009216A FR2481118A1 (fr) | 1980-04-24 | 1980-04-24 | Application a titre de medicaments de derives substitues de l'acide phenyl-4-oxo-2-butenoique |
| SE8102220A SE451838B (sv) | 1980-04-24 | 1981-04-07 | Substituerade 4-fenyl-4-oxo-2-butensyraderivat till anvendning som lekemedel samt farmaceutisk komposition innehallande dessa |
| FR8107803A FR2504005A2 (fr) | 1980-04-24 | 1981-04-17 | Application a titre de medicaments de derives substitues de l'acide 4-phenyl 4-oxo-2-butenoique |
| CA000376022A CA1179601A (fr) | 1980-04-24 | 1981-04-23 | Application a titre de medicaments de derives substitues de l'acide 4-phenyl-4-oxo-2-butenoique |
| BE0/204587A BE888540A (fr) | 1980-04-24 | 1981-04-23 | Application a titre de medicaments de derives substitues de l'acide 1-phenyl 4-oxo 2-butenoique, |
| US06/256,932 US4483868A (en) | 1980-04-24 | 1981-04-23 | Gastro-protecting activity |
| CH2669/81A CH649920A5 (fr) | 1980-04-24 | 1981-04-23 | Derives substitues de l'acide 4-phenyl 4-oxo 2-butenoique, a titre de medicaments. |
| ZA00812672A ZA812672B (en) | 1980-04-24 | 1981-04-23 | Use as medicaments of substituted derivatives of 4-phenyl-4-oxo-2-butenoic acid |
| JP6071281A JPS5726641A (en) | 1980-04-24 | 1981-04-23 | Use of substituted derivative of 4-phenyl-4-oxo-2-butenoic acid as drug |
| IT48336/81A IT1170915B (it) | 1980-04-24 | 1981-04-23 | Derivati sostituiti dell'acido 4-fenil-4-osso-2-butenoico aventi proprieta' farmaceutiche |
| NL8102005A NL8102005A (nl) | 1980-04-24 | 1981-04-23 | Als geneesmiddelen toepasbare gesubstitueerde derivaten van 4-fenyl-4-oxo-2-buteenzuur. |
| AU69803/81A AU543641B2 (en) | 1980-04-24 | 1981-04-24 | Butenoic acid derivatives |
| DE19813116416 DE3116416A1 (de) | 1980-04-24 | 1981-04-24 | "verwendung von substituierten derivaten der 4-phenyl-4-oxo-2-butensaeure als arzneimittel" |
| GB8112679A GB2075836B (en) | 1980-04-24 | 1981-04-24 | Derivatives of 4-phenyl-4-oxo-2-butenoic acid for use as anti ulcer pharmaceuticals |
| SE8700714A SE463366B (sv) | 1980-04-24 | 1987-02-20 | Anvaendning av substituerade 4-fenyl-4-oxo-2-butensyraderivat foer framstaellning av laekemedel foer behandling av sjukdomar i matsmaeltningskanalen och som antiulceroest laekemedel |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8009216A FR2481118A1 (fr) | 1980-04-24 | 1980-04-24 | Application a titre de medicaments de derives substitues de l'acide phenyl-4-oxo-2-butenoique |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2481118A1 true FR2481118A1 (fr) | 1981-10-30 |
| FR2481118B1 FR2481118B1 (US20020095090A1-20020718-M00002.png) | 1983-05-27 |
Family
ID=9241314
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8009216A Granted FR2481118A1 (fr) | 1980-04-24 | 1980-04-24 | Application a titre de medicaments de derives substitues de l'acide phenyl-4-oxo-2-butenoique |
Country Status (13)
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2515175A1 (fr) * | 1981-10-22 | 1983-04-29 | Roussel Uclaf | Nouveaux derives de l'acide 4-phenyl 4-oxo 2-butenoique, leurs sels, leur preparation, leur application comme medicaments et les compositions les renfermant |
| DE3239220A1 (de) * | 1981-10-22 | 1983-05-05 | Roussel-Uclaf, 75007 Paris | Zur verwendung als arzneimittel bestimmte monosubstituierte derivate der 4-phenyl-4-oxo-buten-2-saeure sowie diese enthaltende zusammensetzungen |
| EP0101918A1 (de) * | 1982-08-02 | 1984-03-07 | Henkel Kommanditgesellschaft auf Aktien | Verwendung von Aryloxobutensäure-Derivaten in kosmetischen Mitteln, sowie neue Aryloxobutensäurederivate |
| DE3402313A1 (de) * | 1983-01-24 | 1984-07-26 | Roussel-Uclaf, Paris | Als arzneimittel acrylsaeurederivate mit einem sauerstoff enthaltenden heterocyclus, neue industrielle produkte und herstellungsverfahren |
| FR2567883A2 (fr) * | 1983-01-24 | 1986-01-24 | Roussel Uclaf | Nouveaux derives de l'acide trans 4-oxo 2-butenoique substitues en 4 par un radical furyle, eventuellement substitue a titre de medicaments, produits industriels nouveaux et procede de preparation |
| EP0309262A2 (en) * | 1987-09-25 | 1989-03-29 | Richter Gedeon Vegyeszeti Gyar R.T. | Novel salicylates, their salts, pharmaceutical compositions containing them and process for preparing same |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2504127B1 (fr) * | 1981-04-17 | 1985-07-19 | Roussel Uclaf | Nouveaux derives d'acides phenyl aliphatique carboxyliques, procede pour leur preparation et leur application comme medicaments |
| FR2504004A1 (fr) * | 1981-04-17 | 1982-10-22 | Roussel Uclaf | Application a titre de medicaments de derives d'acides phenyl aliphatique carboxyliques |
| US4649157A (en) * | 1986-03-28 | 1987-03-10 | G. D. Searle & Co. | Pharmaceutical compositions containing 5-phenyl-1,3-dioxoalkenyl compounds |
| IT1190340B (it) * | 1986-06-06 | 1988-02-16 | Roussel Maestretti Spa | Derivati dell'acido 4-fenil 4-osso 2-butenoico,loro procedimento di preparazione e loro impiego come prodotti medicinali |
| DK49688A (da) * | 1987-03-20 | 1988-09-21 | Hoffmann La Roche | Propiolophenonderivater |
| JPH04235142A (ja) * | 1991-01-09 | 1992-08-24 | Kanegafuchi Chem Ind Co Ltd | トランス−β−アロイルアクリル酸エステル類の製造法 |
| JPH064812U (ja) * | 1992-06-29 | 1994-01-21 | オンキヨー株式会社 | 定電流回路 |
| GB9522617D0 (en) * | 1995-11-03 | 1996-01-03 | Pharmacia Spa | 4-Phenyl-4-oxo-butenoic acid derivatives with kynurenine-3-hydroxylase inhibiting activity |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB588108A (en) * | 1944-10-23 | 1947-05-14 | Roche Products Ltd | Manufacture of bacteriostatic substances |
| US2532579A (en) * | 1946-08-06 | 1950-12-05 | Du Pont | Pest control compositions containing beta-acyl acrylates |
| US2562208A (en) * | 1947-04-14 | 1951-07-31 | Schering Corp | Fungistatic composition |
| FR8495M (US20020095090A1-20020718-M00002.png) * | 1966-12-30 | 1973-07-27 | ||
| DE2501834A1 (de) * | 1974-01-17 | 1975-07-24 | Screen | Neue carbonsaeureverbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel |
| CH591415A5 (en) * | 1972-09-13 | 1977-09-15 | Takeda Chemical Industries Ltd | 3-(Tri-substd. benzoyl) propionic acids - as relaxants or spasmolytics for the gall bladder |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1282644B (de) * | 1962-09-08 | 1968-11-14 | Hoechst Ag | Verfahren zur Herstellung von ungesaettigten ª€-Ketocarbonsaeureestern |
| NL6717403A (US20020095090A1-20020718-M00002.png) * | 1966-12-30 | 1968-07-01 | ||
| DE2047806A1 (en) * | 1970-09-29 | 1972-04-06 | Dr Karl Thomae GmbH, 7950 Biberach | 3-aroyl-acrylic acids - pharmaceutical intermediates prepd from acetophenones and glyoxylic acid derivs |
| DE2103749A1 (en) * | 1971-01-27 | 1972-08-10 | Dr. Karl Thomae GmbH, 7951 Biberach | 3-acyl-acrylic acids prepn - from a ketone and glyoxylic acid (deriv) |
| DE2116293A1 (de) * | 1971-04-02 | 1972-10-19 | Cassella Farbwerke Mainkur Ag, 6000 Frankfurt | Ketonderivate und Verfahren zu ihrer Herstellung |
| US3753997A (en) * | 1971-06-07 | 1973-08-21 | A Ash | Trifluoromethly substituted-2,6-diphenyl-4-pyridyl carbinolamine antimalarials |
| BE788749A (fr) * | 1971-09-13 | 1973-03-13 | Takeda Chemical Industries Ltd | Acide 3-(benzoyl trisubstitue)-propionique et son procede de preparation |
| US4017517A (en) * | 1971-09-13 | 1977-04-12 | Takeda Chemical Industries, Ltd. | 2-(Trisubstituted benzoyl)-propionic acid and a method for the production thereof |
| BE795893A (fr) * | 1972-02-28 | 1973-06-18 | Unicler | Derives de (methylene dioxy-3,4 phenyl)-1 dimethyl-4,4 pentene-1, leur preparation et leur application en therrapeutique |
| GB1392100A (en) * | 1972-09-13 | 1975-04-23 | Beecham Group Ltd | Insecticides |
| US3940404A (en) * | 1974-03-06 | 1976-02-24 | The United States Of America As Represented By The Secretary Of The Army | 2-Substituted phenyl-6-trifluoromethyl-4-pyridyl-carbinolamines |
| US3953463A (en) * | 1974-03-06 | 1976-04-27 | The United States Of America As Represented By The Secretary Of The Army | 2-Aryl-6-trifluoromethyl-4-pyridyl-carbinolamine antimalarials |
| JPS5536434A (en) * | 1978-09-07 | 1980-03-14 | Sankyo Co Ltd | 4-phenyl-4-oxo-2-butenoic acid derivative and its preparation |
| ES496382A0 (es) * | 1979-10-31 | 1982-03-01 | Byk Gulden Lomberg Chem Fab | Procedimiento para la preparacion de acidos oxocarboxilicos sustituidos |
| FR2481270A1 (fr) * | 1980-04-24 | 1981-10-30 | Roussel Uclaf | Nouveaux derives substitues de l'acide 4-phenyl 4-oxo 2-hydroxy butanoique, procede pour leur preparation et applications comme medicaments |
-
1980
- 1980-04-24 FR FR8009216A patent/FR2481118A1/fr active Granted
-
1981
- 1981-04-07 SE SE8102220A patent/SE451838B/sv not_active IP Right Cessation
- 1981-04-23 BE BE0/204587A patent/BE888540A/fr not_active IP Right Cessation
- 1981-04-23 CA CA000376022A patent/CA1179601A/fr not_active Expired
- 1981-04-23 NL NL8102005A patent/NL8102005A/nl not_active Application Discontinuation
- 1981-04-23 IT IT48336/81A patent/IT1170915B/it active
- 1981-04-23 JP JP6071281A patent/JPS5726641A/ja active Granted
- 1981-04-23 ZA ZA00812672A patent/ZA812672B/xx unknown
- 1981-04-23 US US06/256,932 patent/US4483868A/en not_active Expired - Fee Related
- 1981-04-23 CH CH2669/81A patent/CH649920A5/fr not_active IP Right Cessation
- 1981-04-24 DE DE19813116416 patent/DE3116416A1/de active Granted
- 1981-04-24 AU AU69803/81A patent/AU543641B2/en not_active Ceased
- 1981-04-24 GB GB8112679A patent/GB2075836B/en not_active Expired
-
1987
- 1987-02-20 SE SE8700714A patent/SE463366B/sv not_active Application Discontinuation
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB588108A (en) * | 1944-10-23 | 1947-05-14 | Roche Products Ltd | Manufacture of bacteriostatic substances |
| US2532579A (en) * | 1946-08-06 | 1950-12-05 | Du Pont | Pest control compositions containing beta-acyl acrylates |
| US2562208A (en) * | 1947-04-14 | 1951-07-31 | Schering Corp | Fungistatic composition |
| FR8495M (US20020095090A1-20020718-M00002.png) * | 1966-12-30 | 1973-07-27 | ||
| CH591415A5 (en) * | 1972-09-13 | 1977-09-15 | Takeda Chemical Industries Ltd | 3-(Tri-substd. benzoyl) propionic acids - as relaxants or spasmolytics for the gall bladder |
| DE2501834A1 (de) * | 1974-01-17 | 1975-07-24 | Screen | Neue carbonsaeureverbindungen, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel |
Non-Patent Citations (3)
| Title |
|---|
| EXBK/48 * |
| EXBK/49 * |
| EXBK/78 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2515175A1 (fr) * | 1981-10-22 | 1983-04-29 | Roussel Uclaf | Nouveaux derives de l'acide 4-phenyl 4-oxo 2-butenoique, leurs sels, leur preparation, leur application comme medicaments et les compositions les renfermant |
| DE3239220A1 (de) * | 1981-10-22 | 1983-05-05 | Roussel-Uclaf, 75007 Paris | Zur verwendung als arzneimittel bestimmte monosubstituierte derivate der 4-phenyl-4-oxo-buten-2-saeure sowie diese enthaltende zusammensetzungen |
| EP0101918A1 (de) * | 1982-08-02 | 1984-03-07 | Henkel Kommanditgesellschaft auf Aktien | Verwendung von Aryloxobutensäure-Derivaten in kosmetischen Mitteln, sowie neue Aryloxobutensäurederivate |
| DE3402313A1 (de) * | 1983-01-24 | 1984-07-26 | Roussel-Uclaf, Paris | Als arzneimittel acrylsaeurederivate mit einem sauerstoff enthaltenden heterocyclus, neue industrielle produkte und herstellungsverfahren |
| FR2546888A1 (fr) * | 1983-01-24 | 1984-12-07 | Roussel Uclaf | Derives de l'acide acrylique comportant un heterocycle renfermant de l'oxygene a titre de medicaments, produits industriels nouveaux et procede de preparation |
| FR2567883A2 (fr) * | 1983-01-24 | 1986-01-24 | Roussel Uclaf | Nouveaux derives de l'acide trans 4-oxo 2-butenoique substitues en 4 par un radical furyle, eventuellement substitue a titre de medicaments, produits industriels nouveaux et procede de preparation |
| EP0309262A2 (en) * | 1987-09-25 | 1989-03-29 | Richter Gedeon Vegyeszeti Gyar R.T. | Novel salicylates, their salts, pharmaceutical compositions containing them and process for preparing same |
| EP0309262A3 (en) * | 1987-09-25 | 1991-04-10 | Richter Gedeon Vegyeszeti Gyar R.T. | Novel salicylates, their salts, pharmaceutical compositions containing them and process for preparing same |
Also Published As
| Publication number | Publication date |
|---|---|
| BE888540A (fr) | 1981-10-23 |
| FR2481118B1 (US20020095090A1-20020718-M00002.png) | 1983-05-27 |
| AU543641B2 (en) | 1985-04-26 |
| DE3116416C2 (US20020095090A1-20020718-M00002.png) | 1990-01-18 |
| ZA812672B (en) | 1982-04-28 |
| SE8102220L (sv) | 1981-10-25 |
| US4483868A (en) | 1984-11-20 |
| CA1179601A (fr) | 1984-12-18 |
| SE463366B (sv) | 1990-11-12 |
| SE451838B (sv) | 1987-11-02 |
| AU6980381A (en) | 1981-10-29 |
| GB2075836A (en) | 1981-11-25 |
| GB2075836B (en) | 1985-03-13 |
| IT8148336A0 (it) | 1981-04-23 |
| NL8102005A (nl) | 1981-11-16 |
| IT1170915B (it) | 1987-06-03 |
| JPH0227326B2 (US20020095090A1-20020718-M00002.png) | 1990-06-15 |
| DE3116416A1 (de) | 1982-04-01 |
| JPS5726641A (en) | 1982-02-12 |
| SE8700714L (sv) | 1987-02-20 |
| SE8700714D0 (sv) | 1987-02-20 |
| CH649920A5 (fr) | 1985-06-28 |
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| CH670823A5 (US20020095090A1-20020718-M00002.png) | ||
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |