CH634551A5 - Process for preparing cinnamides - Google Patents
Process for preparing cinnamides Download PDFInfo
- Publication number
- CH634551A5 CH634551A5 CH125377A CH125377A CH634551A5 CH 634551 A5 CH634551 A5 CH 634551A5 CH 125377 A CH125377 A CH 125377A CH 125377 A CH125377 A CH 125377A CH 634551 A5 CH634551 A5 CH 634551A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- formula
- group
- compound
- trifluoromethyl
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- 239000000460 chlorine Chemical group 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- HQAQWHHPDKFGLV-QPJJXVBHSA-N (e)-n-cyclopropyl-3-[3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound FC(F)(F)C1=CC=CC(\C=C\C(=O)NC2CC2)=C1 HQAQWHHPDKFGLV-QPJJXVBHSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- RTSIUKMGSDOSTI-SNAWJCMRSA-N (e)-3-(3-fluorophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CC(F)=C1 RTSIUKMGSDOSTI-SNAWJCMRSA-N 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- NCOOUEIQXVWKTO-QPJJXVBHSA-N (e)-n-cyclopropyl-3-(3-fluorophenyl)prop-2-enamide Chemical compound FC1=CC=CC(\C=C\C(=O)NC2CC2)=C1 NCOOUEIQXVWKTO-QPJJXVBHSA-N 0.000 claims description 6
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 150000008065 acid anhydrides Chemical class 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 239000011630 iodine Chemical group 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 235000017803 cinnamon Nutrition 0.000 claims description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 241000723347 Cinnamomum Species 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- APEJMQOBVMLION-UHFFFAOYSA-N cinnamamide Chemical class NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
- 239000004615 ingredient Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 6
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 6
- 239000008108 microcrystalline cellulose Substances 0.000 description 6
- 229940016286 microcrystalline cellulose Drugs 0.000 description 6
- 229920002261 Corn starch Polymers 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 239000008120 corn starch Substances 0.000 description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000000377 silicon dioxide Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 235000020357 syrup Nutrition 0.000 description 5
- 239000006188 syrup Substances 0.000 description 5
- LYOVOKZDYQTGTL-SNAWJCMRSA-N (e)-3-(3-fluorophenyl)prop-2-enoyl chloride Chemical compound FC1=CC=CC(\C=C\C(Cl)=O)=C1 LYOVOKZDYQTGTL-SNAWJCMRSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 239000000796 flavoring agent Substances 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- VJMVNRGWCFKKJO-QPJJXVBHSA-N (e)-3-(3-bromophenyl)-n-cyclopropylprop-2-enamide Chemical compound BrC1=CC=CC(\C=C\C(=O)NC2CC2)=C1 VJMVNRGWCFKKJO-QPJJXVBHSA-N 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 3
- 230000002921 anti-spasmodic effect Effects 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 235000013355 food flavoring agent Nutrition 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- NCOOUEIQXVWKTO-UHFFFAOYSA-N n-cyclopropyl-3-(3-fluorophenyl)prop-2-enamide Chemical compound FC1=CC=CC(C=CC(=O)NC2CC2)=C1 NCOOUEIQXVWKTO-UHFFFAOYSA-N 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 3
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 3
- 229920000053 polysorbate 80 Polymers 0.000 description 3
- 229940068968 polysorbate 80 Drugs 0.000 description 3
- 230000002335 preservative effect Effects 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 235000020374 simple syrup Nutrition 0.000 description 3
- 210000002027 skeletal muscle Anatomy 0.000 description 3
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 3
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- KSBWHDDGWSYETA-SNAWJCMRSA-N (E)-3-(trifluoromethyl)cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC(C(F)(F)F)=C1 KSBWHDDGWSYETA-SNAWJCMRSA-N 0.000 description 2
- CVWIVRGJMCHSEZ-VOTSOKGWSA-N (e)-3-(3-bromophenyl)-n-(2-methylpropyl)prop-2-enamide Chemical compound CC(C)CNC(=O)\C=C\C1=CC=CC(Br)=C1 CVWIVRGJMCHSEZ-VOTSOKGWSA-N 0.000 description 2
- OUCPCUKNSDNTMD-SNAWJCMRSA-N (e)-3-(3-bromophenyl)prop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC(Br)=C1 OUCPCUKNSDNTMD-SNAWJCMRSA-N 0.000 description 2
- DKGHNLLBYRFJRC-SNAWJCMRSA-N (e)-3-(3-fluorophenyl)prop-2-enamide Chemical compound NC(=O)\C=C\C1=CC=CC(F)=C1 DKGHNLLBYRFJRC-SNAWJCMRSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- 208000007101 Muscle Cramp Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000007891 compressed tablet Substances 0.000 description 2
- 230000036461 convulsion Effects 0.000 description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 230000011514 reflex Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000829 suppository Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 150000007970 thio esters Chemical class 0.000 description 2
- YEMUSDCFQUBPAL-SNAWJCMRSA-N (e)-3-(3-bromophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CC(Br)=C1 YEMUSDCFQUBPAL-SNAWJCMRSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- CVWIVRGJMCHSEZ-UHFFFAOYSA-N 3-(3-bromophenyl)-n-(2-methylpropyl)prop-2-enamide Chemical compound CC(C)CNC(=O)C=CC1=CC=CC(Br)=C1 CVWIVRGJMCHSEZ-UHFFFAOYSA-N 0.000 description 1
- XKYHWYRDIXTOAX-UHFFFAOYSA-N 3-(3-bromophenyl)-n-cyclobutylprop-2-enamide Chemical compound BrC1=CC=CC(C=CC(=O)NC2CCC2)=C1 XKYHWYRDIXTOAX-UHFFFAOYSA-N 0.000 description 1
- ASYGEDNVHSVFTP-UHFFFAOYSA-N 3-(3-bromophenyl)-n-cycloheptylprop-2-enamide Chemical compound BrC1=CC=CC(C=CC(=O)NC2CCCCCC2)=C1 ASYGEDNVHSVFTP-UHFFFAOYSA-N 0.000 description 1
- FFILVCOQTJBZMW-UHFFFAOYSA-N 3-(3-bromophenyl)-n-cyclohexylprop-2-enamide Chemical compound BrC1=CC=CC(C=CC(=O)NC2CCCCC2)=C1 FFILVCOQTJBZMW-UHFFFAOYSA-N 0.000 description 1
- ZBTSRJMIYOWEDI-UHFFFAOYSA-N 3-(3-bromophenyl)-n-cyclooctylprop-2-enamide Chemical compound BrC1=CC=CC(C=CC(=O)NC2CCCCCCC2)=C1 ZBTSRJMIYOWEDI-UHFFFAOYSA-N 0.000 description 1
- YFZCCSAJORQLPL-UHFFFAOYSA-N 3-(3-bromophenyl)-n-cyclopentylprop-2-enamide Chemical compound BrC1=CC=CC(C=CC(=O)NC2CCCC2)=C1 YFZCCSAJORQLPL-UHFFFAOYSA-N 0.000 description 1
- VJMVNRGWCFKKJO-UHFFFAOYSA-N 3-(3-bromophenyl)-n-cyclopropylprop-2-enamide Chemical compound BrC1=CC=CC(C=CC(=O)NC2CC2)=C1 VJMVNRGWCFKKJO-UHFFFAOYSA-N 0.000 description 1
- KOZDHQSHBDPWGQ-UHFFFAOYSA-N 3-(3-bromophenyl)-n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=CC1=CC=CC(Br)=C1 KOZDHQSHBDPWGQ-UHFFFAOYSA-N 0.000 description 1
- OUCPCUKNSDNTMD-UHFFFAOYSA-N 3-(3-bromophenyl)prop-2-enoyl chloride Chemical compound ClC(=O)C=CC1=CC=CC(Br)=C1 OUCPCUKNSDNTMD-UHFFFAOYSA-N 0.000 description 1
- SIABXCJUNSBMSR-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-(2-methylpropyl)prop-2-enamide Chemical compound CC(C)CNC(=O)C=CC1=CC=CC(Cl)=C1 SIABXCJUNSBMSR-UHFFFAOYSA-N 0.000 description 1
- LLQWQIJQRLZGCH-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-cyclobutylprop-2-enamide Chemical compound ClC1=CC=CC(C=CC(=O)NC2CCC2)=C1 LLQWQIJQRLZGCH-UHFFFAOYSA-N 0.000 description 1
- LLBCLJWCFIGJLH-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-cycloheptylprop-2-enamide Chemical compound ClC1=CC=CC(C=CC(=O)NC2CCCCCC2)=C1 LLBCLJWCFIGJLH-UHFFFAOYSA-N 0.000 description 1
- ZJMYHJJWXYGHKO-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-cyclohexylprop-2-enamide Chemical compound ClC1=CC=CC(C=CC(=O)NC2CCCCC2)=C1 ZJMYHJJWXYGHKO-UHFFFAOYSA-N 0.000 description 1
- RBAHJRZVDYJXBN-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-cyclooctylprop-2-enamide Chemical compound ClC1=CC=CC(C=CC(=O)NC2CCCCCCC2)=C1 RBAHJRZVDYJXBN-UHFFFAOYSA-N 0.000 description 1
- CKQWYISVVILTKG-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-cyclopentylprop-2-enamide Chemical compound ClC1=CC=CC(C=CC(=O)NC2CCCC2)=C1 CKQWYISVVILTKG-UHFFFAOYSA-N 0.000 description 1
- IRIKHRXRQWFJQC-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-cyclopropylprop-2-enamide Chemical compound ClC1=CC=CC(C=CC(=O)NC2CC2)=C1 IRIKHRXRQWFJQC-UHFFFAOYSA-N 0.000 description 1
- MUDQWFVADDJMNM-UHFFFAOYSA-N 3-(3-fluorophenyl)-n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=CC1=CC=CC(F)=C1 MUDQWFVADDJMNM-UHFFFAOYSA-N 0.000 description 1
- DKGHNLLBYRFJRC-UHFFFAOYSA-N 3-(3-fluorophenyl)prop-2-enamide Chemical compound NC(=O)C=CC1=CC=CC(F)=C1 DKGHNLLBYRFJRC-UHFFFAOYSA-N 0.000 description 1
- HGLUKYHWCGEMMR-UHFFFAOYSA-N 3-(3-iodophenyl)-n-(2-methylpropyl)prop-2-enamide Chemical compound CC(C)CNC(=O)C=CC1=CC=CC(I)=C1 HGLUKYHWCGEMMR-UHFFFAOYSA-N 0.000 description 1
- HGQSKTQYEWJJRZ-UHFFFAOYSA-N 3-[3-(trifluoromethyl)phenyl]prop-2-enoyl chloride Chemical compound FC(F)(F)C1=CC=CC(C=CC(Cl)=O)=C1 HGQSKTQYEWJJRZ-UHFFFAOYSA-N 0.000 description 1
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 206010008748 Chorea Diseases 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- 208000034308 Grand mal convulsion Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- 201000002481 Myositis Diseases 0.000 description 1
- GIQDMXXWFNOHPF-UHFFFAOYSA-N N-cyclopropyl-3-[4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound FC(C1=CC=C(C=CC(=O)NC2CC2)C=C1)(F)F GIQDMXXWFNOHPF-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 208000027089 Parkinsonian disease Diseases 0.000 description 1
- 206010034010 Parkinsonism Diseases 0.000 description 1
- 206010061334 Partial seizures Diseases 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 238000003684 Perkin reaction Methods 0.000 description 1
- 206010034759 Petit mal epilepsy Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 208000005392 Spasm Diseases 0.000 description 1
- 201000002661 Spondylitis Diseases 0.000 description 1
- 206010043376 Tetanus Diseases 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001773 anti-convulsant effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 206010008129 cerebral palsy Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 208000012601 choreatic disease Diseases 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 201000005108 complex partial epilepsy Diseases 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- -1 etc. Chemical compound 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 201000007186 focal epilepsy Diseases 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001660 hyperkinetic effect Effects 0.000 description 1
- 230000001631 hypertensive effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000003127 knee Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 239000003158 myorelaxant agent Substances 0.000 description 1
- ACBVXGOUSTUPJP-UHFFFAOYSA-N n-(2-methylpropyl)-3-[3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound CC(C)CNC(=O)C=CC1=CC=CC(C(F)(F)F)=C1 ACBVXGOUSTUPJP-UHFFFAOYSA-N 0.000 description 1
- CZASAKSLHWLFOH-UHFFFAOYSA-N n-cyclobutyl-3-(3-fluorophenyl)prop-2-enamide Chemical compound FC1=CC=CC(C=CC(=O)NC2CCC2)=C1 CZASAKSLHWLFOH-UHFFFAOYSA-N 0.000 description 1
- VLNFULPWFVKYFX-UHFFFAOYSA-N n-cyclobutyl-3-[3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound FC(F)(F)C1=CC=CC(C=CC(=O)NC2CCC2)=C1 VLNFULPWFVKYFX-UHFFFAOYSA-N 0.000 description 1
- MHNSYFDGRRALHL-UHFFFAOYSA-N n-cycloheptyl-3-(3-fluorophenyl)prop-2-enamide Chemical compound FC1=CC=CC(C=CC(=O)NC2CCCCCC2)=C1 MHNSYFDGRRALHL-UHFFFAOYSA-N 0.000 description 1
- FMKOACWNBBYNFN-UHFFFAOYSA-N n-cycloheptyl-3-[3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound FC(F)(F)C1=CC=CC(C=CC(=O)NC2CCCCCC2)=C1 FMKOACWNBBYNFN-UHFFFAOYSA-N 0.000 description 1
- LDEAUXAWEWQLIU-UHFFFAOYSA-N n-cyclohexyl-3-(3-fluorophenyl)prop-2-enamide Chemical compound FC1=CC=CC(C=CC(=O)NC2CCCCC2)=C1 LDEAUXAWEWQLIU-UHFFFAOYSA-N 0.000 description 1
- OIWRPCWKNIEMSU-UHFFFAOYSA-N n-cyclohexyl-3-[3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound FC(F)(F)C1=CC=CC(C=CC(=O)NC2CCCCC2)=C1 OIWRPCWKNIEMSU-UHFFFAOYSA-N 0.000 description 1
- OTACVAFZCVJAMS-UHFFFAOYSA-N n-cyclooctyl-3-(3-fluorophenyl)prop-2-enamide Chemical compound FC1=CC=CC(C=CC(=O)NC2CCCCCCC2)=C1 OTACVAFZCVJAMS-UHFFFAOYSA-N 0.000 description 1
- ORUDCYFNFAPGIU-UHFFFAOYSA-N n-cyclooctyl-3-[3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound FC(F)(F)C1=CC=CC(C=CC(=O)NC2CCCCCCC2)=C1 ORUDCYFNFAPGIU-UHFFFAOYSA-N 0.000 description 1
- HGFJUYNXVPJDAO-UHFFFAOYSA-N n-cyclopentyl-3-(3-fluorophenyl)prop-2-enamide Chemical compound FC1=CC=CC(C=CC(=O)NC2CCCC2)=C1 HGFJUYNXVPJDAO-UHFFFAOYSA-N 0.000 description 1
- VIIXLUGEWGFBOH-UHFFFAOYSA-N n-cyclopentyl-3-(3-iodophenyl)prop-2-enamide Chemical compound IC1=CC=CC(C=CC(=O)NC2CCCC2)=C1 VIIXLUGEWGFBOH-UHFFFAOYSA-N 0.000 description 1
- PIZIXOKAFLWZLH-UHFFFAOYSA-N n-cyclopentyl-3-[3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound FC(F)(F)C1=CC=CC(C=CC(=O)NC2CCCC2)=C1 PIZIXOKAFLWZLH-UHFFFAOYSA-N 0.000 description 1
- GYJLPPVIRHTTAI-UHFFFAOYSA-N n-cyclopropyl-3-(3-iodophenyl)prop-2-enamide Chemical compound IC1=CC=CC(C=CC(=O)NC2CC2)=C1 GYJLPPVIRHTTAI-UHFFFAOYSA-N 0.000 description 1
- HQAQWHHPDKFGLV-UHFFFAOYSA-N n-cyclopropyl-3-[3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound FC(F)(F)C1=CC=CC(C=CC(=O)NC2CC2)=C1 HQAQWHHPDKFGLV-UHFFFAOYSA-N 0.000 description 1
- RSZRIZJHHCIDMV-UHFFFAOYSA-N n-ethyl-3-(3-fluorophenyl)prop-2-enamide Chemical compound CCNC(=O)C=CC1=CC=CC(F)=C1 RSZRIZJHHCIDMV-UHFFFAOYSA-N 0.000 description 1
- FCIHMGBPVMONLW-UHFFFAOYSA-N n-ethyl-3-[3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound CCNC(=O)C=CC1=CC=CC(C(F)(F)F)=C1 FCIHMGBPVMONLW-UHFFFAOYSA-N 0.000 description 1
- YEBIYCKHVHLBHN-UHFFFAOYSA-N n-methyl-3-[3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound CNC(=O)C=CC1=CC=CC(C(F)(F)F)=C1 YEBIYCKHVHLBHN-UHFFFAOYSA-N 0.000 description 1
- CGAMWTJOYCHRLC-UHFFFAOYSA-N n-propan-2-yl-3-[3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound CC(C)NC(=O)C=CC1=CC=CC(C(F)(F)F)=C1 CGAMWTJOYCHRLC-UHFFFAOYSA-N 0.000 description 1
- PIKAUMGVHTWEEJ-UHFFFAOYSA-N n-propyl-3-[3-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound CCCNC(=O)C=CC1=CC=CC(C(F)(F)F)=C1 PIKAUMGVHTWEEJ-UHFFFAOYSA-N 0.000 description 1
- SEFGYZFRYKHSDP-UHFFFAOYSA-N n-tert-butyl-3-(3-iodophenyl)prop-2-enamide Chemical compound CC(C)(C)NC(=O)C=CC1=CC=CC(I)=C1 SEFGYZFRYKHSDP-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000001148 spastic effect Effects 0.000 description 1
- 208000005809 status epilepticus Diseases 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 201000008914 temporal lobe epilepsy Diseases 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical class NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/09—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an acyclic unsaturated carbon skeleton
-
- 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
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/48—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/612—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety
- C07C69/618—Esters of carboxylic acids having a carboxyl group bound to an acyclic carbon atom and having a six-membered aromatic ring in the acid moiety having unsaturation outside the six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (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)
- Indole Compounds (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH504182A CH635820A5 (en) | 1976-02-03 | 1982-08-24 | Process for preparing cinnamides |
| CH504282A CH636849A5 (en) | 1976-02-03 | 1982-08-25 | Process for the preparation of cinnamamides |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB416976 | 1976-02-03 | ||
| GB4168/76A GB1568401A (en) | 1976-02-03 | 1976-02-03 | Biologically active amides |
| GB417076 | 1976-02-03 | ||
| US71213476A | 1976-08-06 | 1976-08-06 | |
| US71213576A | 1976-08-06 | 1976-08-06 | |
| US71231876A | 1976-08-06 | 1976-08-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH634551A5 true CH634551A5 (en) | 1983-02-15 |
Family
ID=27546490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH125377A CH634551A5 (en) | 1976-02-03 | 1977-02-02 | Process for preparing cinnamides |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS6056700B2 (enExample) |
| AR (1) | AR218865A1 (enExample) |
| AT (1) | AT363926B (enExample) |
| BE (1) | BE851020A (enExample) |
| CA (1) | CA1109076A (enExample) |
| CH (1) | CH634551A5 (enExample) |
| CS (2) | CS245756B2 (enExample) |
| DD (1) | DD130349A5 (enExample) |
| DE (1) | DE2704365C2 (enExample) |
| DK (1) | DK43177A (enExample) |
| FI (1) | FI69625C (enExample) |
| FR (1) | FR2340303A1 (enExample) |
| GB (1) | GB1568401A (enExample) |
| GR (1) | GR66474B (enExample) |
| HU (1) | HU175435B (enExample) |
| IE (1) | IE44862B1 (enExample) |
| IL (1) | IL51373A (enExample) |
| NL (1) | NL7701088A (enExample) |
| PL (2) | PL119314B1 (enExample) |
| SE (2) | SE436870B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104432097A (zh) * | 2014-12-16 | 2015-03-25 | 段占娥 | 一种缓解体力疲劳的天然增补剂 |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0714871B2 (ja) * | 1989-02-02 | 1995-02-22 | 大正製薬株式会社 | 筋弛緩剤 |
| DE19931116A1 (de) * | 1999-07-06 | 2001-01-11 | Bayer Ag | Verfahren zur Herstellung von Phenethylaminen und neue chemische Verbindungen |
| CN104513172B (zh) * | 2013-09-30 | 2018-02-02 | 天士力医药集团股份有限公司 | 含有三氟甲基的酰胺生物碱、制备方法及其药物用途 |
-
1976
- 1976-02-03 GB GB4168/76A patent/GB1568401A/en not_active Expired
-
1977
- 1977-02-02 FI FI770365A patent/FI69625C/fi not_active IP Right Cessation
- 1977-02-02 IE IE212/77A patent/IE44862B1/en unknown
- 1977-02-02 CH CH125377A patent/CH634551A5/de not_active IP Right Cessation
- 1977-02-02 JP JP52010599A patent/JPS6056700B2/ja not_active Expired
- 1977-02-02 BE BE174605A patent/BE851020A/xx not_active IP Right Cessation
- 1977-02-02 FR FR7702865A patent/FR2340303A1/fr active Granted
- 1977-02-02 PL PL1977214782A patent/PL119314B1/pl unknown
- 1977-02-02 SE SE7701107A patent/SE436870B/xx not_active IP Right Cessation
- 1977-02-02 DK DK43177A patent/DK43177A/da not_active Application Discontinuation
- 1977-02-02 AT AT0065277A patent/AT363926B/de not_active IP Right Cessation
- 1977-02-02 AR AR266409A patent/AR218865A1/es active
- 1977-02-02 DD DD7700197200A patent/DD130349A5/xx not_active IP Right Cessation
- 1977-02-02 GR GR52690A patent/GR66474B/el unknown
- 1977-02-02 HU HU77WE549A patent/HU175435B/hu not_active IP Right Cessation
- 1977-02-02 PL PL1977195740A patent/PL119716B1/pl not_active IP Right Cessation
- 1977-02-02 IL IL51373A patent/IL51373A/xx unknown
- 1977-02-02 NL NL7701088A patent/NL7701088A/xx not_active Application Discontinuation
- 1977-02-02 DE DE2704365A patent/DE2704365C2/de not_active Expired
- 1977-02-02 CS CS77695A patent/CS245756B2/cs unknown
- 1977-02-02 CA CA270,904A patent/CA1109076A/en not_active Expired
- 1977-02-02 CS CS777652A patent/CS245758B2/cs unknown
-
1983
- 1983-01-28 SE SE8300432A patent/SE8300432L/sv not_active Application Discontinuation
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104432097A (zh) * | 2014-12-16 | 2015-03-25 | 段占娥 | 一种缓解体力疲劳的天然增补剂 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2340303A1 (fr) | 1977-09-02 |
| PL195740A1 (pl) | 1979-05-07 |
| SE436870B (sv) | 1985-01-28 |
| DE2704365A1 (de) | 1977-08-04 |
| DK43177A (da) | 1977-08-04 |
| AR218865A1 (es) | 1980-07-15 |
| DD130349A5 (de) | 1978-03-22 |
| GB1568401A (en) | 1980-05-29 |
| PL119716B1 (en) | 1982-01-30 |
| FI69625B (fi) | 1985-11-29 |
| JPS6056700B2 (ja) | 1985-12-11 |
| ATA65277A (de) | 1981-02-15 |
| HU175435B (hu) | 1980-07-28 |
| SE8300432D0 (sv) | 1983-01-28 |
| FI69625C (fi) | 1986-03-10 |
| GR66474B (enExample) | 1981-03-23 |
| AT363926B (de) | 1981-09-10 |
| IL51373A (en) | 1981-12-31 |
| SE7701107L (sv) | 1977-08-04 |
| PL119314B1 (en) | 1981-12-31 |
| NL7701088A (nl) | 1977-08-05 |
| JPS52116437A (en) | 1977-09-29 |
| DE2704365C2 (de) | 1986-03-20 |
| FI770365A7 (enExample) | 1977-08-04 |
| IE44862L (en) | 1977-08-03 |
| IE44862B1 (en) | 1982-04-21 |
| CS245758B2 (en) | 1986-10-16 |
| CS245756B2 (en) | 1986-10-16 |
| BE851020A (fr) | 1977-08-02 |
| SE8300432L (sv) | 1983-01-28 |
| CA1109076A (en) | 1981-09-15 |
| IL51373A0 (en) | 1977-04-29 |
| FR2340303B1 (enExample) | 1979-04-13 |
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