CH616650A5 - - Google Patents
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- Publication number
- CH616650A5 CH616650A5 CH1039275A CH1039275A CH616650A5 CH 616650 A5 CH616650 A5 CH 616650A5 CH 1039275 A CH1039275 A CH 1039275A CH 1039275 A CH1039275 A CH 1039275A CH 616650 A5 CH616650 A5 CH 616650A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acid
- trans
- formula
- acid amide
- bromo
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 description 28
- 238000000034 method Methods 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- 241000699670 Mus sp. Species 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- 238000010992 reflux Methods 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- 150000001412 amines Chemical class 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- LDCXGZCEMNMWIL-VOTSOKGWSA-N cinromide Chemical compound CCNC(=O)\C=C\C1=CC=CC(Br)=C1 LDCXGZCEMNMWIL-VOTSOKGWSA-N 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 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 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 238000002329 infrared spectrum Methods 0.000 description 5
- 210000003141 lower extremity Anatomy 0.000 description 5
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 125000001246 bromo group Chemical group Br* 0.000 description 4
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 239000011630 iodine Chemical group 0.000 description 4
- 229910052740 iodine Chemical group 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- -1 trans-3-bromocinnamyl chloride Chemical compound 0.000 description 4
- 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 3
- 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 3
- LDCXGZCEMNMWIL-UHFFFAOYSA-N 3-(3-bromophenyl)-n-ethylprop-2-enamide Chemical compound CCNC(=O)C=CC1=CC=CC(Br)=C1 LDCXGZCEMNMWIL-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 206010010904 Convulsion Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- APEJMQOBVMLION-UHFFFAOYSA-N cinnamamide Chemical class NC(=O)C=CC1=CC=CC=C1 APEJMQOBVMLION-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- MSSAFCYKWMNVMZ-VOTSOKGWSA-N ethyl (e)-3-(3-bromophenyl)prop-2-enoate Chemical compound CCOC(=O)\C=C\C1=CC=CC(Br)=C1 MSSAFCYKWMNVMZ-VOTSOKGWSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 229920000609 methyl cellulose Polymers 0.000 description 3
- 239000001923 methylcellulose Substances 0.000 description 3
- 235000010981 methylcellulose Nutrition 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- WXDKSHWEVCMKPK-UHFFFAOYSA-N 3-(3-bromophenyl)-n-methylprop-2-enamide Chemical compound CNC(=O)C=CC1=CC=CC(Br)=C1 WXDKSHWEVCMKPK-UHFFFAOYSA-N 0.000 description 2
- VEGFRDDLDFXXGY-UHFFFAOYSA-N 3-(3-bromophenyl)-n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)C=CC1=CC=CC(Br)=C1 VEGFRDDLDFXXGY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HTPJRPPDRGOHFT-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-ethylprop-2-enamide Chemical compound CCNC(=O)C=CC1=CC=CC(Cl)=C1 HTPJRPPDRGOHFT-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000001773 anti-convulsant effect Effects 0.000 description 2
- 230000002921 anti-spasmodic effect Effects 0.000 description 2
- 239000001961 anticonvulsive agent Substances 0.000 description 2
- 229960003965 antiepileptics Drugs 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- APEJMQOBVMLION-VOTSOKGWSA-N trans-cinnamamide Chemical compound NC(=O)\C=C\C1=CC=CC=C1 APEJMQOBVMLION-VOTSOKGWSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- WXDKSHWEVCMKPK-AATRIKPKSA-N (e)-3-(3-bromophenyl)-n-methylprop-2-enamide Chemical compound CNC(=O)\C=C\C1=CC=CC(Br)=C1 WXDKSHWEVCMKPK-AATRIKPKSA-N 0.000 description 1
- VEGFRDDLDFXXGY-VOTSOKGWSA-N (e)-3-(3-bromophenyl)-n-propan-2-ylprop-2-enamide Chemical compound CC(C)NC(=O)\C=C\C1=CC=CC(Br)=C1 VEGFRDDLDFXXGY-VOTSOKGWSA-N 0.000 description 1
- PIGPCZZJBZXVBF-SNAWJCMRSA-N (e)-3-(3-bromophenyl)prop-2-enamide Chemical compound NC(=O)\C=C\C1=CC=CC(Br)=C1 PIGPCZZJBZXVBF-SNAWJCMRSA-N 0.000 description 1
- HTPJRPPDRGOHFT-VOTSOKGWSA-N (e)-3-(3-chlorophenyl)-n-ethylprop-2-enamide Chemical compound CCNC(=O)\C=C\C1=CC=CC(Cl)=C1 HTPJRPPDRGOHFT-VOTSOKGWSA-N 0.000 description 1
- SCNRDAIXZJFMEX-SNAWJCMRSA-N (e)-3-(3-chlorophenyl)prop-2-enoyl chloride Chemical compound ClC(=O)\C=C\C1=CC=CC(Cl)=C1 SCNRDAIXZJFMEX-SNAWJCMRSA-N 0.000 description 1
- XQOFQTFBKOHMCW-SNAWJCMRSA-N (e)-3-(3-iodophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CC(I)=C1 XQOFQTFBKOHMCW-SNAWJCMRSA-N 0.000 description 1
- GQPXDUZITOCERA-VOTSOKGWSA-N (e)-n-ethyl-3-(3-iodophenyl)prop-2-enamide Chemical compound CCNC(=O)\C=C\C1=CC=CC(I)=C1 GQPXDUZITOCERA-VOTSOKGWSA-N 0.000 description 1
- ZWAVGZYKJNOTPX-UHFFFAOYSA-N 1,3-diethylurea Chemical compound CCNC(=O)NCC ZWAVGZYKJNOTPX-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BEDSJQWRRJYSRA-UHFFFAOYSA-N 3-(3-bromophenyl)-n-propylprop-2-enamide Chemical compound CCCNC(=O)C=CC1=CC=CC(Br)=C1 BEDSJQWRRJYSRA-UHFFFAOYSA-N 0.000 description 1
- PIGPCZZJBZXVBF-UHFFFAOYSA-N 3-(3-bromophenyl)prop-2-enamide Chemical compound NC(=O)C=CC1=CC=CC(Br)=C1 PIGPCZZJBZXVBF-UHFFFAOYSA-N 0.000 description 1
- WLDLUGXUGDYTOM-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-methylprop-2-enamide Chemical compound CNC(=O)C=CC1=CC=CC(Cl)=C1 WLDLUGXUGDYTOM-UHFFFAOYSA-N 0.000 description 1
- ZKZBHVPWUJOHCG-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-propylprop-2-enamide Chemical compound CCCNC(=O)C=CC1=CC=CC(Cl)=C1 ZKZBHVPWUJOHCG-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000723347 Cinnamomum Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 208000034308 Grand mal convulsion Diseases 0.000 description 1
- 238000006000 Knoevenagel condensation reaction Methods 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 206010061334 Partial seizures Diseases 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
- 241000906446 Theraps Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 239000011230 binding agent Substances 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
- 238000007707 calorimetry Methods 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 201000005108 complex partial epilepsy Diseases 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000000265 homogenisation 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
- 238000002955 isolation Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 201000003040 photosensitive epilepsy Diseases 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 201000005070 reflex epilepsy Diseases 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 201000008914 temporal lobe epilepsy Diseases 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07C233/11—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB35279/74A GB1519762A (en) | 1974-08-09 | 1974-08-09 | Cinnamamides their preparation and pharmaceutical compositions containing them |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH616650A5 true CH616650A5 (pl) | 1980-04-15 |
Family
ID=10375925
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1039275A CH616650A5 (pl) | 1974-08-09 | 1975-08-08 | |
| CH1093979A CH639067A5 (de) | 1974-08-09 | 1979-12-10 | Verfahren zur herstellung von zimtsaeureamiden. |
| CH1093879A CH636339A5 (de) | 1974-08-09 | 1979-12-10 | Verfahren zur herstellung von zimtsaeureamiden. |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1093979A CH639067A5 (de) | 1974-08-09 | 1979-12-10 | Verfahren zur herstellung von zimtsaeureamiden. |
| CH1093879A CH636339A5 (de) | 1974-08-09 | 1979-12-10 | Verfahren zur herstellung von zimtsaeureamiden. |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4041071A (pl) |
| JP (1) | JPS588387B2 (pl) |
| AR (2) | AR213275A1 (pl) |
| AT (2) | AT350531B (pl) |
| AU (1) | AU498222B2 (pl) |
| BE (1) | BE832283A (pl) |
| CA (1) | CA1075714A (pl) |
| CH (3) | CH616650A5 (pl) |
| CS (1) | CS209864B2 (pl) |
| CY (1) | CY1110A (pl) |
| DD (1) | DD123311A5 (pl) |
| DE (1) | DE2535599C2 (pl) |
| DK (1) | DK360975A (pl) |
| ES (3) | ES440140A1 (pl) |
| FI (1) | FI752257A (pl) |
| FR (1) | FR2281109A1 (pl) |
| GB (1) | GB1519762A (pl) |
| HK (1) | HK20881A (pl) |
| HU (1) | HU174875B (pl) |
| IE (1) | IE41444B1 (pl) |
| IL (1) | IL47892A (pl) |
| IT (1) | IT8047984A0 (pl) |
| NL (1) | NL7509482A (pl) |
| PL (5) | PL118454B1 (pl) |
| SE (1) | SE424316B (pl) |
| SU (1) | SU728712A3 (pl) |
| ZA (1) | ZA755127B (pl) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4190674A (en) * | 1976-02-03 | 1980-02-26 | Burroughs Wellcome Co. | 3-Fluoro-N-cyclopropylcinnamide |
| US4107320A (en) * | 1976-08-06 | 1978-08-15 | Burroughs Wellcome Co. | Biologically active amides |
| US4183858A (en) * | 1977-07-01 | 1980-01-15 | Merrell Toraude Et Compagnie | α-Vinyl tryptophanes |
| US4179524A (en) * | 1978-06-16 | 1979-12-18 | Burroughs Wellcome Co. | Biologically active amide |
| DE4421536A1 (de) * | 1994-06-20 | 1995-12-21 | Hoechst Ag | Perfluoralkylgruppen tragende phenylsubstituierte Alkenylcarbonsäure-guanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament |
| KR100492809B1 (ko) * | 2001-11-23 | 2005-06-03 | 한국화학연구원 | 항산화 활성을 갖는 4-히드록시 신남아미드 유도체, 그의제조방법 및 이를 포함하는 약학적 조성물 |
| PL209602B1 (pl) | 2005-10-20 | 2011-09-30 | Inst Chemii Bioorg Pan | Sposób otrzymywania amidu kwasu 3-(4-hydroksyfenylo)propanowego |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1131728A (en) | 1966-05-10 | 1968-10-23 | Smith Kline French Lab | N,n-dimethylcinnamamides |
| GB1128142A (en) | 1966-06-30 | 1968-09-25 | James Lincoln Bezemek | Wear indicating arrangement for vehicle power transfer devices |
| US3444197A (en) | 1966-09-27 | 1969-05-13 | Upjohn Co | 3,4-dihalocinnamamides |
| US3538156A (en) | 1967-07-24 | 1970-11-03 | Herbert Schwartz | Cinnamamides |
| CH533113A (de) * | 1967-12-01 | 1973-03-15 | Thomae Gmbh Dr K | Verfahren zur Herstellung von neuen Zimtsäureamiden |
| US3488749A (en) * | 1968-01-29 | 1970-01-06 | Smithkline Corp | Antidepressant n,n-dimethylcinnamamide compositions and methods |
| CH510021A (de) | 1968-11-05 | 1971-07-15 | Thomae Gmbh Dr K | Verfahren zur Herstellung neuer Zimtsäureamide |
| FR2040181A1 (pl) * | 1969-04-02 | 1971-01-22 | Lipha | |
| CA1174865A (en) | 1971-04-16 | 1984-09-25 | Ferenc M. Pallos | Thiolcarbamate herbicides containing nitrogen containing antidote |
-
1974
- 1974-08-09 GB GB35279/74A patent/GB1519762A/en not_active Expired
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1975
- 1975-07-17 US US05/596,653 patent/US4041071A/en not_active Expired - Lifetime
- 1975-08-08 CS CS755508A patent/CS209864B2/cs unknown
- 1975-08-08 AT AT618175A patent/AT350531B/de not_active IP Right Cessation
- 1975-08-08 CH CH1039275A patent/CH616650A5/de not_active IP Right Cessation
- 1975-08-08 AU AU83789/75A patent/AU498222B2/en not_active Expired
- 1975-08-08 HU HU75WE526A patent/HU174875B/hu unknown
- 1975-08-08 ES ES440140A patent/ES440140A1/es not_active Expired
- 1975-08-08 CA CA233,157A patent/CA1075714A/en not_active Expired
- 1975-08-08 FI FI752257A patent/FI752257A/fi not_active Application Discontinuation
- 1975-08-08 SE SE7508936A patent/SE424316B/xx unknown
- 1975-08-08 PL PL1975217610A patent/PL118454B1/pl unknown
- 1975-08-08 DD DD187766A patent/DD123311A5/xx unknown
- 1975-08-08 DE DE2535599A patent/DE2535599C2/de not_active Expired
- 1975-08-08 IE IE1760/75A patent/IE41444B1/en unknown
- 1975-08-08 NL NL7509482A patent/NL7509482A/xx not_active Application Discontinuation
- 1975-08-08 PL PL1975182629A patent/PL101781B1/pl unknown
- 1975-08-08 BE BE159078A patent/BE832283A/xx unknown
- 1975-08-08 DK DK360975A patent/DK360975A/da unknown
- 1975-08-08 SU SU752163175A patent/SU728712A3/ru active
- 1975-08-08 IL IL47892A patent/IL47892A/xx unknown
- 1975-08-08 PL PL1975201096A patent/PL101758B1/pl unknown
- 1975-08-08 ZA ZA755127A patent/ZA755127B/xx unknown
- 1975-08-08 AR AR259950A patent/AR213275A1/es active
- 1975-08-08 PL PL1975201097A patent/PL110755B1/pl unknown
- 1975-08-08 JP JP50096600A patent/JPS588387B2/ja not_active Expired
- 1975-08-08 PL PL1975217609A patent/PL118238B1/pl unknown
- 1975-08-08 FR FR7524783A patent/FR2281109A1/fr active Granted
- 1975-11-07 CY CY1110A patent/CY1110A/xx unknown
-
1976
- 1976-11-06 ES ES453101A patent/ES453101A1/es not_active Expired
- 1976-11-06 ES ES453100A patent/ES453100A1/es not_active Expired
-
1977
- 1977-02-01 AT AT61977A patent/AT346314B/de not_active IP Right Cessation
- 1977-08-04 AR AR264203A patent/AR211436Q/es unknown
-
1979
- 1979-12-10 CH CH1093979A patent/CH639067A5/de not_active IP Right Cessation
- 1979-12-10 CH CH1093879A patent/CH636339A5/de not_active IP Right Cessation
-
1980
- 1980-02-22 IT IT8047984A patent/IT8047984A0/it unknown
-
1981
- 1981-05-14 HK HK208/81A patent/HK20881A/xx unknown
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