CA1109076A - Biologically active amides - Google Patents
Biologically active amidesInfo
- Publication number
- CA1109076A CA1109076A CA270,904A CA270904A CA1109076A CA 1109076 A CA1109076 A CA 1109076A CA 270904 A CA270904 A CA 270904A CA 1109076 A CA1109076 A CA 1109076A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- acid
- compound
- fluoro
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001408 amides Chemical class 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 57
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 13
- -1 chloro, bromo, iodo Chemical group 0.000 claims abstract description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 44
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 11
- 150000001412 amines Chemical class 0.000 claims description 10
- 239000007788 liquid Substances 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- 150000008065 acid anhydrides Chemical class 0.000 claims description 5
- APEJMQOBVMLION-UHFFFAOYSA-N cinnamamide Chemical compound NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 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 4
- 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
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 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 claims description 3
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000012433 hydrogen halide Substances 0.000 claims description 3
- 229910000039 hydrogen halide Inorganic materials 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 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
- 238000002360 preparation method Methods 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 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
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 2
- 239000003209 petroleum derivative Substances 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
- 239000001117 sulphuric acid Substances 0.000 claims description 2
- 235000011149 sulphuric acid Nutrition 0.000 claims description 2
- 150000003672 ureas Chemical class 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 230000000875 corresponding effect Effects 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 125000002346 iodo group Chemical group I* 0.000 claims 1
- 230000001773 anti-convulsant effect Effects 0.000 abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000000203 mixture Substances 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 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 description 6
- 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
- 238000010992 reflux Methods 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- 206010010904 Convulsion Diseases 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- 240000008042 Zea mays Species 0.000 description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 5
- 235000005822 corn Nutrition 0.000 description 5
- 239000005350 fused silica glass Substances 0.000 description 5
- 235000019359 magnesium stearate Nutrition 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000006188 syrup Substances 0.000 description 5
- 235000020357 syrup Nutrition 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
- 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 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 230000000694 effects Effects 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
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 4
- 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 4
- 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 4
- 239000003755 preservative agent Substances 0.000 description 4
- 238000011321 prophylaxis Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 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
- 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
- 239000001961 anticonvulsive agent Substances 0.000 description 3
- 229960003965 antiepileptics Drugs 0.000 description 3
- 239000001768 carboxy methyl cellulose Substances 0.000 description 3
- 239000007891 compressed tablet Substances 0.000 description 3
- 230000036461 convulsion Effects 0.000 description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 235000013355 food flavoring agent Nutrition 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-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
- 230000000144 pharmacologic effect Effects 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
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 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
- 229960004016 sucrose syrup Drugs 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- 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
- HGQSKTQYEWJJRZ-SNAWJCMRSA-N (e)-3-[3-(trifluoromethyl)phenyl]prop-2-enoyl chloride Chemical compound FC(F)(F)C1=CC=CC(\C=C\C(Cl)=O)=C1 HGQSKTQYEWJJRZ-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
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 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
- 238000004566 IR spectroscopy Methods 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
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000002775 capsule Substances 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
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003814 drug Substances 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
- 239000008101 lactose Substances 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 239000003158 myorelaxant agent Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000008194 pharmaceutical composition Substances 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
- 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
- KWQSNWNWCQKYNG-UHFFFAOYSA-N 3-(3-bromophenyl)-n-(cyclohexylmethyl)prop-2-enamide Chemical compound BrC1=CC=CC(C=CC(=O)NCC2CCCCC2)=C1 KWQSNWNWCQKYNG-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
- 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
- 208000009017 Athetosis Diseases 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 206010008748 Chorea Diseases 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 208000034308 Grand mal convulsion Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- 208000007101 Muscle Cramp Diseases 0.000 description 1
- 201000002481 Myositis Diseases 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
- 238000006680 Reformatsky reaction Methods 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
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-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
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003937 drug carrier 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
- 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
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 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
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 230000003387 muscular Effects 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
- 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
- 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
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000012501 relaxation of skeletal muscle Effects 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001148 spastic effect Effects 0.000 description 1
- 208000005809 status epilepticus Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 201000008914 temporal lobe epilepsy Diseases 0.000 description 1
- 230000008719 thickening Effects 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
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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)
Applications Claiming Priority (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4169/76 | 1976-02-03 | ||
| GB4168/76A GB1568401A (en) | 1976-02-03 | 1976-02-03 | Biologically active amides |
| GB4168/76 | 1976-02-03 | ||
| GB416976 | 1976-02-03 | ||
| GB417076 | 1976-02-03 | ||
| GB4170/76 | 1976-02-03 | ||
| US71231876A | 1976-08-06 | 1976-08-06 | |
| US71213576A | 1976-08-06 | 1976-08-06 | |
| US71213476A | 1976-08-06 | 1976-08-06 | |
| US712,134 | 1976-08-06 | ||
| US712,135 | 1976-08-06 | ||
| US712,318 | 1976-08-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1109076A true CA1109076A (en) | 1981-09-15 |
Family
ID=27546490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA270,904A Expired CA1109076A (en) | 1976-02-03 | 1977-02-02 | Biologically active amides |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS6056700B2 (sv) |
| AR (1) | AR218865A1 (sv) |
| AT (1) | AT363926B (sv) |
| BE (1) | BE851020A (sv) |
| CA (1) | CA1109076A (sv) |
| CH (1) | CH634551A5 (sv) |
| CS (2) | CS245756B2 (sv) |
| DD (1) | DD130349A5 (sv) |
| DE (1) | DE2704365C2 (sv) |
| DK (1) | DK43177A (sv) |
| FI (1) | FI69625C (sv) |
| FR (1) | FR2340303A1 (sv) |
| GB (1) | GB1568401A (sv) |
| GR (1) | GR66474B (sv) |
| HU (1) | HU175435B (sv) |
| IE (1) | IE44862B1 (sv) |
| IL (1) | IL51373A (sv) |
| NL (1) | NL7701088A (sv) |
| PL (2) | PL119716B1 (sv) |
| SE (2) | SE436870B (sv) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5116877A (en) * | 1989-02-02 | 1992-05-26 | Taisho Pharmaceutical Co., Ltd. | Pharmaceutical use for cinnamamide derivatives |
| 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 |
| CN104432097B (zh) * | 2014-12-16 | 2016-08-17 | 广州渔夫堡医药科技有限公司 | 一种缓解体力疲劳的天然增补剂 |
-
1976
- 1976-02-03 GB GB4168/76A patent/GB1568401A/en not_active Expired
-
1977
- 1977-02-02 DD DD7700197200A patent/DD130349A5/xx not_active IP Right Cessation
- 1977-02-02 FI FI770365A patent/FI69625C/fi not_active IP Right Cessation
- 1977-02-02 CS CS77695A patent/CS245756B2/cs unknown
- 1977-02-02 AT AT0065277A patent/AT363926B/de not_active IP Right Cessation
- 1977-02-02 BE BE174605A patent/BE851020A/xx not_active IP Right Cessation
- 1977-02-02 CS CS777652A patent/CS245758B2/cs unknown
- 1977-02-02 GR GR52690A patent/GR66474B/el unknown
- 1977-02-02 CA CA270,904A patent/CA1109076A/en not_active Expired
- 1977-02-02 AR AR266409A patent/AR218865A1/es active
- 1977-02-02 NL NL7701088A patent/NL7701088A/xx not_active Application Discontinuation
- 1977-02-02 SE SE7701107A patent/SE436870B/sv not_active IP Right Cessation
- 1977-02-02 PL PL1977195740A patent/PL119716B1/pl not_active IP Right Cessation
- 1977-02-02 JP JP52010599A patent/JPS6056700B2/ja not_active Expired
- 1977-02-02 DE DE2704365A patent/DE2704365C2/de not_active Expired
- 1977-02-02 PL PL1977214782A patent/PL119314B1/pl unknown
- 1977-02-02 IL IL51373A patent/IL51373A/xx unknown
- 1977-02-02 CH CH125377A patent/CH634551A5/de not_active IP Right Cessation
- 1977-02-02 HU HU77WE549A patent/HU175435B/hu not_active IP Right Cessation
- 1977-02-02 DK DK43177A patent/DK43177A/da not_active Application Discontinuation
- 1977-02-02 FR FR7702865A patent/FR2340303A1/fr active Granted
- 1977-02-02 IE IE212/77A patent/IE44862B1/en unknown
-
1983
- 1983-01-28 SE SE8300432A patent/SE8300432D0/sv not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| HU175435B (hu) | 1980-07-28 |
| DK43177A (da) | 1977-08-04 |
| SE8300432L (sv) | 1983-01-28 |
| AT363926B (de) | 1981-09-10 |
| FR2340303A1 (fr) | 1977-09-02 |
| FR2340303B1 (sv) | 1979-04-13 |
| DE2704365A1 (de) | 1977-08-04 |
| JPS52116437A (en) | 1977-09-29 |
| DD130349A5 (de) | 1978-03-22 |
| IE44862L (en) | 1977-08-03 |
| CS245756B2 (en) | 1986-10-16 |
| IL51373A (en) | 1981-12-31 |
| FI69625C (fi) | 1986-03-10 |
| CS245758B2 (en) | 1986-10-16 |
| AR218865A1 (es) | 1980-07-15 |
| GB1568401A (en) | 1980-05-29 |
| PL195740A1 (pl) | 1979-05-07 |
| DE2704365C2 (de) | 1986-03-20 |
| FI770365A (sv) | 1977-08-04 |
| PL119314B1 (en) | 1981-12-31 |
| JPS6056700B2 (ja) | 1985-12-11 |
| SE7701107L (sv) | 1977-08-04 |
| PL119716B1 (en) | 1982-01-30 |
| CH634551A5 (en) | 1983-02-15 |
| IL51373A0 (en) | 1977-04-29 |
| BE851020A (fr) | 1977-08-02 |
| NL7701088A (nl) | 1977-08-05 |
| FI69625B (fi) | 1985-11-29 |
| ATA65277A (de) | 1981-02-15 |
| SE8300432D0 (sv) | 1983-01-28 |
| SE436870B (sv) | 1985-01-28 |
| GR66474B (sv) | 1981-03-23 |
| IE44862B1 (en) | 1982-04-21 |
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