CH659243A5 - Carbonsaeureamidverbindungen und ihre derivate. - Google Patents
Carbonsaeureamidverbindungen und ihre derivate. Download PDFInfo
- Publication number
- CH659243A5 CH659243A5 CH2883/84A CH288384A CH659243A5 CH 659243 A5 CH659243 A5 CH 659243A5 CH 2883/84 A CH2883/84 A CH 2883/84A CH 288384 A CH288384 A CH 288384A CH 659243 A5 CH659243 A5 CH 659243A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- group
- aminocarbonyl
- dimethyl
- hydrogen atom
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims description 48
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 title 1
- -1 Carboxamide compound Chemical class 0.000 claims description 71
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 38
- 150000003839 salts Chemical class 0.000 claims description 19
- FKOPGCJIAFSDAO-UHFFFAOYSA-N 1-methylcyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1(C)CCC=CC1 FKOPGCJIAFSDAO-UHFFFAOYSA-N 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 8
- 230000002490 cerebral effect Effects 0.000 claims description 7
- 206010015037 epilepsy Diseases 0.000 claims description 7
- 208000024891 symptom Diseases 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- ZBJJJVAZHYEDET-UHFFFAOYSA-N 6-[[3,5-bis(trifluoromethyl)phenyl]carbamoyl]-3,4-dimethylcyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CC(C)=C(C)CC1C(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 ZBJJJVAZHYEDET-UHFFFAOYSA-N 0.000 claims description 4
- WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000002521 alkyl halide group Chemical group 0.000 claims description 4
- 230000001079 digestive effect Effects 0.000 claims description 4
- 208000019553 vascular disease Diseases 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- MEVHTHLQPUQANE-UHFFFAOYSA-N aziridine-2,3-dione Chemical compound O=C1NC1=O MEVHTHLQPUQANE-UHFFFAOYSA-N 0.000 claims 2
- 108090000623 proteins and genes Proteins 0.000 claims 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 1
- 206010019196 Head injury Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 150000004820 halides Chemical group 0.000 claims 1
- 125000001475 halogen functional group Chemical group 0.000 claims 1
- 125000004970 halomethyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 238000000921 elemental analysis Methods 0.000 description 44
- 238000002844 melting Methods 0.000 description 33
- 230000008018 melting Effects 0.000 description 33
- 239000002253 acid Substances 0.000 description 15
- 159000000000 sodium salts Chemical class 0.000 description 12
- 241000699670 Mus sp. Species 0.000 description 11
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- 206010010904 Convulsion Diseases 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 230000001771 impaired effect Effects 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000003449 preventive effect Effects 0.000 description 4
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- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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- 239000008273 gelatin Substances 0.000 description 3
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- 235000019322 gelatine Nutrition 0.000 description 3
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- 208000014674 injury Diseases 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
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- 239000011734 sodium Substances 0.000 description 3
- 230000008733 trauma Effects 0.000 description 3
- 238000005303 weighing Methods 0.000 description 3
- XVMHMVDTROABSK-UHFFFAOYSA-N 2-(3,5-dichlorophenyl)-5-methyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C(C)=CCC(C2=O)C1C(=O)N2C1=CC(Cl)=CC(Cl)=C1 XVMHMVDTROABSK-UHFFFAOYSA-N 0.000 description 2
- OYZPZDVVDGUGJH-UHFFFAOYSA-N 2-(3,5-dimethylphenyl)-5-methyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C(C)=CCC(C2=O)C1C(=O)N2C1=CC(C)=CC(C)=C1 OYZPZDVVDGUGJH-UHFFFAOYSA-N 0.000 description 2
- SSIFECZGUBWWED-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-5-methyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C(C)=CCC(C2=O)C1C(=O)N2C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 SSIFECZGUBWWED-UHFFFAOYSA-N 0.000 description 2
- YURNCBVQZBJDAJ-UHFFFAOYSA-N 2-heptenoic acid Chemical compound CCCCC=CC(O)=O YURNCBVQZBJDAJ-UHFFFAOYSA-N 0.000 description 2
- UWGJHXAQRXPUAB-UHFFFAOYSA-N 3,4-dimethyl-6-(phenylcarbamoyl)cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CC(C)=C(C)CC1C(=O)NC1=CC=CC=C1 UWGJHXAQRXPUAB-UHFFFAOYSA-N 0.000 description 2
- MPNAVCFVLWBLCI-UHFFFAOYSA-N 3,4-dimethyl-6-[(4-methylphenyl)carbamoyl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CC(C)=C(C)CC1C(=O)NC1=CC=C(C)C=C1 MPNAVCFVLWBLCI-UHFFFAOYSA-N 0.000 description 2
- VDBPMDLICMFYOB-UHFFFAOYSA-N 6-[(3,5-dichlorophenyl)carbamoyl]-3,4-dimethylcyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CC(C)=C(C)CC1C(=O)NC1=CC(Cl)=CC(Cl)=C1 VDBPMDLICMFYOB-UHFFFAOYSA-N 0.000 description 2
- KOTAEYIGZGZJQW-UHFFFAOYSA-N 6-[(3-chlorophenyl)carbamoyl]-3,4-dimethylcyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CC(C)=C(C)CC1C(=O)NC1=CC=CC(Cl)=C1 KOTAEYIGZGZJQW-UHFFFAOYSA-N 0.000 description 2
- RWXGSIZUGMFQJI-UHFFFAOYSA-N 6-[(4-chlorophenyl)carbamoyl]-3,4-dimethylcyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CC(C)=C(C)CC1C(=O)NC1=CC=C(Cl)C=C1 RWXGSIZUGMFQJI-UHFFFAOYSA-N 0.000 description 2
- NKDSQCOOZMPVPQ-UHFFFAOYSA-N 6-[[2-chloro-5-(trifluoromethyl)phenyl]carbamoyl]-3,4-dimethylcyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CC(C)=C(C)CC1C(=O)NC1=CC(C(F)(F)F)=CC=C1Cl NKDSQCOOZMPVPQ-UHFFFAOYSA-N 0.000 description 2
- 206010002091 Anaesthesia Diseases 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- 208000026139 Memory disease Diseases 0.000 description 2
- 208000016285 Movement disease Diseases 0.000 description 2
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 210000001015 abdomen Anatomy 0.000 description 2
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- 230000006931 brain damage Effects 0.000 description 2
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- 229910052791 calcium Inorganic materials 0.000 description 2
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 239000000812 cholinergic antagonist Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
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- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 2
- 210000004798 organs belonging to the digestive system Anatomy 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
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- AQKACENWDQZESU-PBOULFJWSA-N (2E,4E)-N-isobutyl-7-(3,4-methylenedioxyphenyl)-hepta-2,4-dienamide Chemical compound CC(C)CNC(=O)\C=C\C=C\CCC1=CC=C2OCOC2=C1 AQKACENWDQZESU-PBOULFJWSA-N 0.000 description 1
- LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-N 0.000 description 1
- CECCXJUWRKJNSQ-VYKNHSEDSA-N (4R,4aR,7S,7aR,12bS)-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol ethyl carbamate Chemical compound CCOC(N)=O.O[C@H]([C@@H]1O2)C=C[C@H]3[C@]4([H])N(C)CC[C@]13C1=C2C(O)=CC=C1C4 CECCXJUWRKJNSQ-VYKNHSEDSA-N 0.000 description 1
- JSQQHMFSUKLZSE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-methyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C(C)=CCC(C2=O)C1C(=O)N2C1=CC=CC=C1Cl JSQQHMFSUKLZSE-UHFFFAOYSA-N 0.000 description 1
- FUSWZQXPUSGYPO-UHFFFAOYSA-N 2-(3-chlorophenyl)-5,6-dimethyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C(C)=C(C)CC(C2=O)C1C(=O)N2C1=CC=CC(Cl)=C1 FUSWZQXPUSGYPO-UHFFFAOYSA-N 0.000 description 1
- QWIJLLKDJZVJRQ-UHFFFAOYSA-N 2-(3-chlorophenyl)-5-methyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C(C)=CCC(C2=O)C1C(=O)N2C1=CC=CC(Cl)=C1 QWIJLLKDJZVJRQ-UHFFFAOYSA-N 0.000 description 1
- WGPBEPVLHUAUFV-UHFFFAOYSA-N 2-(3-ethylphenyl)-5,6-dimethyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound CCC1=CC=CC(N2C(C3CC(C)=C(C)CC3C2=O)=O)=C1 WGPBEPVLHUAUFV-UHFFFAOYSA-N 0.000 description 1
- SPPKVZDGPPSGAK-UHFFFAOYSA-N 2-(4-bromophenyl)-5-methyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C(C)=CCC(C2=O)C1C(=O)N2C1=CC=C(Br)C=C1 SPPKVZDGPPSGAK-UHFFFAOYSA-N 0.000 description 1
- DCDKOXKFGLOBNY-UHFFFAOYSA-N 2-(4-chloro-2-methylphenyl)-5,6-dimethyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C(C)=C(C)CC(C2=O)C1C(=O)N2C1=CC=C(Cl)C=C1C DCDKOXKFGLOBNY-UHFFFAOYSA-N 0.000 description 1
- RSTTZEFIQUOSMC-UHFFFAOYSA-N 2-(4-chlorophenyl)-5,6-dimethyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C(C)=C(C)CC(C2=O)C1C(=O)N2C1=CC=C(Cl)C=C1 RSTTZEFIQUOSMC-UHFFFAOYSA-N 0.000 description 1
- AYXQXJZFOINROG-UHFFFAOYSA-N 2-(4-methoxyphenyl)-5-methyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1=CC(OC)=CC=C1N1C(=O)C2CC(C)=CCC2C1=O AYXQXJZFOINROG-UHFFFAOYSA-N 0.000 description 1
- AWOYNIFVZKAAKO-UHFFFAOYSA-N 2-[2-chloro-5-(trifluoromethyl)phenyl]-5,6-dimethyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C(C)=C(C)CC(C2=O)C1C(=O)N2C1=CC(C(F)(F)F)=CC=C1Cl AWOYNIFVZKAAKO-UHFFFAOYSA-N 0.000 description 1
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- KTWWYKNJEXQFHC-UHFFFAOYSA-N 2-[3,5-bis(trifluoromethyl)phenyl]-5,6-dimethyl-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C(C)=C(C)CC(C2=O)C1C(=O)N2C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 KTWWYKNJEXQFHC-UHFFFAOYSA-N 0.000 description 1
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- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- BRFYLSHOWYVWBU-UHFFFAOYSA-N 3-methyl-6-(phenylcarbamoyl)cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CC(C)=CCC1C(=O)NC1=CC=CC=C1 BRFYLSHOWYVWBU-UHFFFAOYSA-N 0.000 description 1
- AOHHVUGEFHDKKA-UHFFFAOYSA-N 3-methyl-6-[(2-methylphenyl)carbamoyl]cyclohex-3-ene-1-carboxylic acid Chemical compound OC(=O)C1CC(C)=CCC1C(=O)NC1=CC=CC=C1C AOHHVUGEFHDKKA-UHFFFAOYSA-N 0.000 description 1
- MTWZRIQAZWCMNK-UHFFFAOYSA-N 3-methyl-6-[(4-propylphenyl)carbamoyl]cyclohex-3-ene-1-carboxylic acid Chemical compound C1=CC(CCC)=CC=C1NC(=O)C1C(C(O)=O)CC(C)=CC1 MTWZRIQAZWCMNK-UHFFFAOYSA-N 0.000 description 1
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- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
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- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/166—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the carbon of a carboxamide group directly attached to the aromatic ring, e.g. procainamide, procarbazine, metoclopramide, labetalol
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- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58104873A JPS59231057A (ja) | 1983-06-14 | 1983-06-14 | カルボン酸アミド化合物およびその誘導体 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH659243A5 true CH659243A5 (de) | 1987-01-15 |
Family
ID=14392332
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH2883/84A CH659243A5 (de) | 1983-06-14 | 1984-06-14 | Carbonsaeureamidverbindungen und ihre derivate. |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4596826A (en, 2012) |
| JP (1) | JPS59231057A (en, 2012) |
| KR (1) | KR850001153A (en, 2012) |
| AU (1) | AU582117B2 (en, 2012) |
| BE (1) | BE899918A (en, 2012) |
| CA (1) | CA1215992A (en, 2012) |
| CH (1) | CH659243A5 (en, 2012) |
| DE (1) | DE3421929A1 (en, 2012) |
| DK (1) | DK289684A (en, 2012) |
| ES (2) | ES533372A0 (en, 2012) |
| FR (1) | FR2548180B1 (en, 2012) |
| GB (1) | GB2141713B (en, 2012) |
| HU (1) | HU191674B (en, 2012) |
| IT (1) | IT1180188B (en, 2012) |
| NL (1) | NL8401890A (en, 2012) |
| PH (2) | PH20503A (en, 2012) |
| SE (1) | SE8403168L (en, 2012) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59118750A (ja) * | 1982-12-27 | 1984-07-09 | Eisai Co Ltd | カルボン酸アミド化合物およびその誘導体 |
| EP0302934A4 (en) * | 1987-02-26 | 1990-12-12 | Nippon Zeon Co., Ltd. | Alicyclic dicarboxylic acid derivatives and muscle relaxants containing them as effective ingredients |
| JP4663748B2 (ja) * | 2008-03-10 | 2011-04-06 | 三菱重工交通機器エンジニアリング株式会社 | ボーディングブリッジの接続部およびボーディングブリッジ |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2774787A (en) * | 1953-09-03 | 1956-12-18 | Charles F Geschickter | Polyhydrophthalamic acid visceral smooth muscle relaxants |
| US3131509A (en) * | 1961-05-08 | 1964-05-05 | Spencer Chem Co | Compositions and methods for reducing herbicidal injury |
| US3507904A (en) * | 1966-04-01 | 1970-04-21 | Herbert Schwartz | Novel tetrahydrophthalamic acids and derivatives thereof |
| US3745170A (en) * | 1969-03-19 | 1973-07-10 | Sumitomo Chemical Co | Novel n-(3,5-dihalophenyl)-imide compounds |
| US3654302A (en) * | 1970-01-30 | 1972-04-04 | Herbert Schwartz | Tetrahydrophthalanils |
| JPS4882038A (en, 2012) * | 1972-02-08 | 1973-11-02 | ||
| US3987056A (en) * | 1973-05-07 | 1976-10-19 | Phillips Petroleum Company | Disproportionation of n-aryl-1,2,3,6-tetrahydrophthalimides |
| US4002460A (en) * | 1974-03-13 | 1977-01-11 | Stauffer Chemical Company | Triazine-antidote compositions and methods of use for cotton |
| US3996043A (en) * | 1975-04-10 | 1976-12-07 | Stauffer Chemical Company | Triazine--antidote compositions and methods of use for cotton |
| PT71116A (de) * | 1979-04-20 | 1980-05-01 | Ciba Geigy Ag | Verfahren zur herstellung neuer cyclobutandicarbonsaureimide |
| JPS56169669A (en) * | 1980-05-30 | 1981-12-26 | Takeda Chem Ind Ltd | Hexahydroisoindole derivative, its preparation and herbicide |
| JPS59118750A (ja) * | 1982-12-27 | 1984-07-09 | Eisai Co Ltd | カルボン酸アミド化合物およびその誘導体 |
-
1983
- 1983-06-14 JP JP58104873A patent/JPS59231057A/ja active Granted
-
1984
- 1984-06-11 PH PH30801A patent/PH20503A/en unknown
- 1984-06-11 CA CA000456279A patent/CA1215992A/en not_active Expired
- 1984-06-12 US US06/620,050 patent/US4596826A/en not_active Expired - Fee Related
- 1984-06-13 IT IT21378/84A patent/IT1180188B/it active
- 1984-06-13 SE SE8403168A patent/SE8403168L/xx not_active Application Discontinuation
- 1984-06-13 DE DE19843421929 patent/DE3421929A1/de not_active Withdrawn
- 1984-06-13 ES ES533372A patent/ES533372A0/es active Granted
- 1984-06-13 DK DK289684A patent/DK289684A/da not_active Application Discontinuation
- 1984-06-13 HU HU842278A patent/HU191674B/hu not_active IP Right Cessation
- 1984-06-14 FR FR8409341A patent/FR2548180B1/fr not_active Expired
- 1984-06-14 KR KR1019840003332A patent/KR850001153A/ko not_active Ceased
- 1984-06-14 BE BE0/213145A patent/BE899918A/fr not_active IP Right Cessation
- 1984-06-14 CH CH2883/84A patent/CH659243A5/de not_active IP Right Cessation
- 1984-06-14 NL NL8401890A patent/NL8401890A/nl not_active Application Discontinuation
- 1984-06-14 AU AU29379/84A patent/AU582117B2/en not_active Ceased
- 1984-06-14 GB GB08415153A patent/GB2141713B/en not_active Expired
-
1985
- 1985-07-16 ES ES545252A patent/ES8603824A1/es not_active Expired
- 1985-12-12 PH PH33166A patent/PH21315A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1215992A (en) | 1986-12-30 |
| SE8403168L (sv) | 1984-12-15 |
| ES8603383A1 (es) | 1985-12-16 |
| PH20503A (en) | 1987-01-21 |
| DE3421929A1 (de) | 1984-12-20 |
| ES533372A0 (es) | 1985-12-16 |
| BE899918A (fr) | 1984-12-14 |
| SE8403168D0 (sv) | 1984-06-13 |
| DK289684A (da) | 1984-12-15 |
| AU582117B2 (en) | 1989-03-16 |
| ES545252A0 (es) | 1986-01-01 |
| US4596826A (en) | 1986-06-24 |
| GB8415153D0 (en) | 1984-07-18 |
| PH21315A (en) | 1987-09-28 |
| HU191674B (en) | 1987-03-30 |
| IT8421378A1 (it) | 1985-12-13 |
| GB2141713A (en) | 1985-01-03 |
| DK289684D0 (da) | 1984-06-13 |
| KR850001153A (ko) | 1985-03-16 |
| AU2937984A (en) | 1984-12-20 |
| HUT36084A (en) | 1985-08-28 |
| GB2141713B (en) | 1987-06-10 |
| JPH0136820B2 (en, 2012) | 1989-08-02 |
| NL8401890A (nl) | 1985-01-02 |
| JPS59231057A (ja) | 1984-12-25 |
| FR2548180A1 (fr) | 1985-01-04 |
| IT1180188B (it) | 1987-09-23 |
| IT8421378A0 (it) | 1984-06-13 |
| ES8603824A1 (es) | 1986-01-01 |
| FR2548180B1 (fr) | 1987-06-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |