IE51797B1 - Carboxamide compounds as srs-a antagonists and a process for producing same - Google Patents
Carboxamide compounds as srs-a antagonists and a process for producing sameInfo
- Publication number
- IE51797B1 IE51797B1 IE2511/81A IE251181A IE51797B1 IE 51797 B1 IE51797 B1 IE 51797B1 IE 2511/81 A IE2511/81 A IE 2511/81A IE 251181 A IE251181 A IE 251181A IE 51797 B1 IE51797 B1 IE 51797B1
- Authority
- IE
- Ireland
- Prior art keywords
- formula
- compound
- hydrogen
- compounds
- alkyl
- Prior art date
Links
- -1 Carboxamide compounds Chemical class 0.000 title claims description 41
- 238000000034 method Methods 0.000 title claims description 19
- 239000005557 antagonist Substances 0.000 title description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 107
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 46
- 238000002360 preparation method Methods 0.000 claims description 39
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 7
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 claims description 3
- HIJQFTSZBHDYKW-UHFFFAOYSA-N 4,4-dimethyloxane-2,6-dione Chemical compound CC1(C)CC(=O)OC(=O)C1 HIJQFTSZBHDYKW-UHFFFAOYSA-N 0.000 claims description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 229940014800 succinic anhydride Drugs 0.000 claims description 3
- MGICRVTUCPFQQZ-UHFFFAOYSA-N 4-methyloxane-2,6-dione Chemical compound CC1CC(=O)OC(=O)C1 MGICRVTUCPFQQZ-UHFFFAOYSA-N 0.000 claims description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 12
- AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical class NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 abstract description 9
- 206010002198 Anaphylactic reaction Diseases 0.000 abstract description 8
- 230000036783 anaphylactic response Effects 0.000 abstract description 8
- 208000003455 anaphylaxis Diseases 0.000 abstract description 8
- 230000000172 allergic effect Effects 0.000 abstract description 5
- 208000010668 atopic eczema Diseases 0.000 abstract description 5
- 206010039085 Rhinitis allergic Diseases 0.000 abstract description 4
- 201000010105 allergic rhinitis Diseases 0.000 abstract description 4
- 208000006673 asthma Diseases 0.000 abstract description 4
- 150000002148 esters Chemical class 0.000 abstract description 4
- 208000030603 inherited susceptibility to asthma Diseases 0.000 abstract description 4
- 208000027771 Obstructive airways disease Diseases 0.000 abstract description 3
- 208000017520 skin disease Diseases 0.000 abstract description 3
- 230000003042 antagnostic effect Effects 0.000 abstract description 2
- NQQRXZOPZBKCNF-UHFFFAOYSA-N but-2-enamide Chemical class CC=CC(N)=O NQQRXZOPZBKCNF-UHFFFAOYSA-N 0.000 abstract 1
- 230000003033 spasmogenic effect Effects 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 72
- 239000000243 solution Substances 0.000 description 64
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 41
- 239000002904 solvent Substances 0.000 description 39
- 239000000047 product Substances 0.000 description 25
- 239000007787 solid Substances 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000001704 evaporation Methods 0.000 description 21
- 230000008020 evaporation Effects 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- 229960000583 acetic acid Drugs 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 16
- 230000009102 absorption Effects 0.000 description 15
- 238000010521 absorption reaction Methods 0.000 description 15
- 238000001914 filtration Methods 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000011541 reaction mixture Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 239000012362 glacial acetic acid Substances 0.000 description 10
- 150000002431 hydrogen Chemical group 0.000 description 10
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 10
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical class NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 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 9
- 238000010992 reflux Methods 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 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 6
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- BIHOAKPNPOGWEV-DTWKUNHWSA-N (1r,2r)-2-(4-nitrophenyl)cyclopropane-1-carboxylic acid Chemical compound OC(=O)[C@@H]1C[C@H]1C1=CC=C([N+]([O-])=O)C=C1 BIHOAKPNPOGWEV-DTWKUNHWSA-N 0.000 description 4
- NQQRXZOPZBKCNF-NSCUHMNNSA-N (e)-but-2-enamide Chemical compound C\C=C\C(N)=O NQQRXZOPZBKCNF-NSCUHMNNSA-N 0.000 description 4
- YDEVXEVUHMTVDR-UHFFFAOYSA-N 3-(3-aminophenyl)-n-undecan-2-ylbut-2-enamide Chemical compound CCCCCCCCCC(C)NC(=O)C=C(C)C1=CC=CC(N)=C1 YDEVXEVUHMTVDR-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 150000008064 anhydrides Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 125000006501 nitrophenyl group Chemical group 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 239000002002 slurry Substances 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- NHBKWZCTSMCKDS-UHFFFAOYSA-N undecan-2-amine Chemical compound CCCCCCCCCC(C)N NHBKWZCTSMCKDS-UHFFFAOYSA-N 0.000 description 4
- DMXDUJPYGUWROU-UHFFFAOYSA-N 2-methyl-3-(3-nitrophenyl)prop-2-enoic acid Chemical compound OC(=O)C(C)=CC1=CC=CC([N+]([O-])=O)=C1 DMXDUJPYGUWROU-UHFFFAOYSA-N 0.000 description 3
- IAAYIMSCXZZMNL-UHFFFAOYSA-N 3-(3-nitrophenyl)-n-undecan-2-ylbut-2-enamide Chemical compound CCCCCCCCCC(C)NC(=O)C=C(C)C1=CC=CC([N+]([O-])=O)=C1 IAAYIMSCXZZMNL-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000003213 activating effect Effects 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
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- 238000001990 intravenous administration Methods 0.000 description 3
- 210000003205 muscle Anatomy 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- GOIOMLHBTYITHL-RBUKOAKNSA-N (1r,2r)-n-decyl-2-(4-nitrophenyl)cyclopropane-1-carboxamide Chemical compound CCCCCCCCCCNC(=O)[C@@H]1C[C@H]1C1=CC=C([N+]([O-])=O)C=C1 GOIOMLHBTYITHL-RBUKOAKNSA-N 0.000 description 2
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KFTHUBZIEMOORC-UHFFFAOYSA-N 2-methylbut-2-enamide Chemical compound CC=C(C)C(N)=O KFTHUBZIEMOORC-UHFFFAOYSA-N 0.000 description 2
- BBQDLDVSEDAYAA-AATRIKPKSA-N 2-nitrocinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1[N+]([O-])=O BBQDLDVSEDAYAA-AATRIKPKSA-N 0.000 description 2
- VOEIMOANYYOUNN-UHFFFAOYSA-N 3-(3-nitrophenyl)but-2-enoic acid Chemical compound OC(=O)C=C(C)C1=CC=CC([N+]([O-])=O)=C1 VOEIMOANYYOUNN-UHFFFAOYSA-N 0.000 description 2
- ORIBWNWUGUWUKV-UHFFFAOYSA-N 3-(3-nitrophenyl)prop-2-enoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C=CC(Cl)=O)=C1 ORIBWNWUGUWUKV-UHFFFAOYSA-N 0.000 description 2
- ZETIVVHRRQLWFW-UHFFFAOYSA-N 3-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC(C=O)=C1 ZETIVVHRRQLWFW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
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- 229910014570 C—OH Inorganic materials 0.000 description 2
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- 101100518501 Mus musculus Spp1 gene Proteins 0.000 description 2
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- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 2
- FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 2
- YWGRWUCXXBYRFF-UHFFFAOYSA-N ethyl 3-(3-nitrophenyl)but-2-enoate Chemical compound CCOC(=O)C=C(C)C1=CC=CC([N+]([O-])=O)=C1 YWGRWUCXXBYRFF-UHFFFAOYSA-N 0.000 description 2
- GXKAVJLXZLKIAJ-UHFFFAOYSA-N ethyl 3-(4-nitrophenyl)but-2-enoate Chemical compound CCOC(=O)C=C(C)C1=CC=C([N+]([O-])=O)C=C1 GXKAVJLXZLKIAJ-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229960001340 histamine Drugs 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
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- 229910052742 iron Inorganic materials 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- DZLUCCVCCOVAHN-UHFFFAOYSA-N n-decyl-3-(2-nitrophenyl)prop-2-enamide Chemical compound CCCCCCCCCCNC(=O)C=CC1=CC=CC=C1[N+]([O-])=O DZLUCCVCCOVAHN-UHFFFAOYSA-N 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/56—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups bound to carbon atoms of six-membered aromatic rings and carboxyl groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/55—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/201,894 US4296129A (en) | 1980-10-29 | 1980-10-29 | (Carboxyacylamino)phenylalkenamides and esters thereof as SRS-A antagonists |
| US06/292,387 US4331683A (en) | 1980-10-29 | 1981-08-13 | Carboxamide compounds as SRS-A antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE812511L IE812511L (en) | 1982-04-29 |
| IE51797B1 true IE51797B1 (en) | 1987-04-01 |
Family
ID=26897189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2511/81A IE51797B1 (en) | 1980-10-29 | 1981-10-27 | Carboxamide compounds as srs-a antagonists and a process for producing same |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4331683A (enExample) |
| EP (1) | EP0050977B1 (enExample) |
| AU (1) | AU7689681A (enExample) |
| DE (1) | DE3160883D1 (enExample) |
| DK (1) | DK475381A (enExample) |
| GR (1) | GR75391B (enExample) |
| IE (1) | IE51797B1 (enExample) |
| IL (1) | IL64150A0 (enExample) |
| PT (1) | PT73895B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2526422B1 (fr) * | 1982-05-06 | 1985-09-20 | Roussel Uclaf | Nouveau procede de preparation de derives de l'acide cyclopropane carboxylique |
| DE3515278A1 (de) * | 1985-04-27 | 1986-10-30 | Grünenthal GmbH, 5190 Stolberg | Neue benzoesaeurederivate, diese enthaltende arzneimittel und verfahren zur herstellung dieser verbindungen und arzneimittel |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3966965A (en) * | 1973-03-23 | 1976-06-29 | American Home Products Corporation | Oxamic acid derivatives for the prevention of immediate type hypersensitivity reactions |
| US4061791A (en) * | 1975-12-29 | 1977-12-06 | The Upjohn Company | Anti-allergic oxanilate compounds |
-
1981
- 1981-08-13 US US06/292,387 patent/US4331683A/en not_active Expired - Lifetime
- 1981-10-26 GR GR66360A patent/GR75391B/el unknown
- 1981-10-26 DE DE8181305024T patent/DE3160883D1/de not_active Expired
- 1981-10-26 EP EP81305024A patent/EP0050977B1/en not_active Expired
- 1981-10-27 IE IE2511/81A patent/IE51797B1/en unknown
- 1981-10-28 AU AU76896/81A patent/AU7689681A/en not_active Abandoned
- 1981-10-28 IL IL64150A patent/IL64150A0/xx unknown
- 1981-10-28 DK DK475381A patent/DK475381A/da not_active Application Discontinuation
- 1981-10-28 PT PT73895A patent/PT73895B/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK475381A (da) | 1982-04-30 |
| DE3160883D1 (en) | 1983-10-20 |
| AU7689681A (en) | 1982-05-06 |
| EP0050977B1 (en) | 1983-09-14 |
| EP0050977A1 (en) | 1982-05-05 |
| GR75391B (enExample) | 1984-07-13 |
| IL64150A0 (en) | 1982-01-31 |
| IE812511L (en) | 1982-04-29 |
| US4331683A (en) | 1982-05-25 |
| PT73895B (en) | 1983-06-28 |
| PT73895A (en) | 1981-11-01 |
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