NO880352L - Fremgangsmaate for fremstilling av 4-aryl-n-(2-(dialkylamino og heterocyklisk amino)alkyl)-1-piperazincarboxamider. - Google Patents
Fremgangsmaate for fremstilling av 4-aryl-n-(2-(dialkylamino og heterocyklisk amino)alkyl)-1-piperazincarboxamider.Info
- Publication number
- NO880352L NO880352L NO880352A NO880352A NO880352L NO 880352 L NO880352 L NO 880352L NO 880352 A NO880352 A NO 880352A NO 880352 A NO880352 A NO 880352A NO 880352 L NO880352 L NO 880352L
- Authority
- NO
- Norway
- Prior art keywords
- ethyl
- piperazinecarboxamide
- dimethylamino
- mol
- phenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 62
- -1 AMINO Chemical class 0.000 title claims description 40
- 238000002360 preparation method Methods 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 136
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 239000012458 free base Substances 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- UXVMHPDFGRRXPH-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(4-nitrophenyl)piperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCN(C)C)CCN1C1=CC=C([N+]([O-])=O)C=C1 UXVMHPDFGRRXPH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 3
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- UAZPZIWLIHPPAJ-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)-n-[2-(dimethylamino)ethyl]piperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCN(C)C)CCN1C1=CC=C(Cl)C(Cl)=C1 UAZPZIWLIHPPAJ-UHFFFAOYSA-N 0.000 claims description 2
- XMRJZABWSNOFGA-UHFFFAOYSA-N 4-(4-chlorophenyl)-n-[2-(dimethylamino)ethyl]piperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCN(C)C)CCN1C1=CC=C(Cl)C=C1 XMRJZABWSNOFGA-UHFFFAOYSA-N 0.000 claims description 2
- NYZKRRCGNAMLNT-UHFFFAOYSA-N 4-phenyl-n-(2-pyrrolidin-1-ylethyl)piperazine-1-carboxamide Chemical compound C1CN(C=2C=CC=CC=2)CCN1C(=O)NCCN1CCCC1 NYZKRRCGNAMLNT-UHFFFAOYSA-N 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 150000001734 carboxylic acid salts Chemical class 0.000 claims description 2
- HZBZEYXAHTVQKW-UHFFFAOYSA-N n-(1-ethylpiperidin-3-yl)-4-phenylpiperazine-1-carboxamide Chemical compound C1N(CC)CCCC1NC(=O)N1CCN(C=2C=CC=CC=2)CC1 HZBZEYXAHTVQKW-UHFFFAOYSA-N 0.000 claims description 2
- KTUSITLQMUDEFW-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(2-methoxyphenyl)piperazine-1-carboxamide Chemical compound COC1=CC=CC=C1N1CCN(C(=O)NCCN(C)C)CC1 KTUSITLQMUDEFW-UHFFFAOYSA-N 0.000 claims description 2
- GOAJGCDPZXUQDR-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(3-methoxyphenyl)piperazine-1-carboxamide Chemical compound COC1=CC=CC(N2CCN(CC2)C(=O)NCCN(C)C)=C1 GOAJGCDPZXUQDR-UHFFFAOYSA-N 0.000 claims description 2
- YMWSDSKUNYUOKR-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(4-fluorophenyl)piperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCN(C)C)CCN1C1=CC=C(F)C=C1 YMWSDSKUNYUOKR-UHFFFAOYSA-N 0.000 claims description 2
- BGFQALRPQNDUKA-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(4-methoxyphenyl)piperazine-1-carboxamide Chemical compound C1=CC(OC)=CC=C1N1CCN(C(=O)NCCN(C)C)CC1 BGFQALRPQNDUKA-UHFFFAOYSA-N 0.000 claims description 2
- XXYRQOAFNOQOER-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(4-methylphenyl)piperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCN(C)C)CCN1C1=CC=C(C)C=C1 XXYRQOAFNOQOER-UHFFFAOYSA-N 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 239000005864 Sulphur Chemical group 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 claims 1
- ZGSDJMADBJCNPN-UHFFFAOYSA-N [S-][NH3+] Chemical compound [S-][NH3+] ZGSDJMADBJCNPN-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 118
- 239000007787 solid Substances 0.000 description 93
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 63
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 59
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 58
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 56
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 54
- 239000000203 mixture Substances 0.000 description 52
- 238000004458 analytical method Methods 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 25
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 241001465754 Metazoa Species 0.000 description 16
- 239000003208 petroleum Substances 0.000 description 16
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 13
- 235000011121 sodium hydroxide Nutrition 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 11
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 11
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 239000000706 filtrate Substances 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 238000001665 trituration Methods 0.000 description 7
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000007792 addition Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 210000002683 foot Anatomy 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 230000003266 anti-allergic effect Effects 0.000 description 5
- 239000000427 antigen Substances 0.000 description 5
- 102000036639 antigens Human genes 0.000 description 5
- 108091007433 antigens Proteins 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- AVJKDKWRVSSJPK-UHFFFAOYSA-N 1-(4-fluorophenyl)piperazine Chemical compound C1=CC(F)=CC=C1N1CCNCC1 AVJKDKWRVSSJPK-UHFFFAOYSA-N 0.000 description 4
- 241000700198 Cavia Species 0.000 description 4
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- 208000026935 allergic disease Diseases 0.000 description 4
- 239000003054 catalyst Substances 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
- 239000002904 solvent Substances 0.000 description 4
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- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 4
- YMDZDFSUDFLGMX-UHFFFAOYSA-N 2-chloro-n-(2-chloroethyl)ethanamine;hydron;chloride Chemical compound [Cl-].ClCC[NH2+]CCCl YMDZDFSUDFLGMX-UHFFFAOYSA-N 0.000 description 3
- WRXNJTBODVGDRY-UHFFFAOYSA-N 2-pyrrolidin-1-ylethanamine Chemical compound NCCN1CCCC1 WRXNJTBODVGDRY-UHFFFAOYSA-N 0.000 description 3
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- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
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- 238000010253 intravenous injection Methods 0.000 description 2
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- STSMIHZKPXEPTM-UHFFFAOYSA-N n-[2-(azetidin-1-yl)ethyl]-4-phenylpiperazine-1-carboxamide Chemical compound C1CN(C=2C=CC=CC=2)CCN1C(=O)NCCN1CCC1 STSMIHZKPXEPTM-UHFFFAOYSA-N 0.000 description 1
- AKAXBYHYGDWYIQ-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-4-phenylpiperazine-1-carboxamide;oxalic acid Chemical compound OC(=O)C(O)=O.C1CN(C(=O)NCCN(CC)CC)CCN1C1=CC=CC=C1 AKAXBYHYGDWYIQ-UHFFFAOYSA-N 0.000 description 1
- FMONGVQGMINZKH-UHFFFAOYSA-N n-[2-(diethylamino)ethyl]-4-phenylpiperazine-1-carboxamide;oxalic acid;hydrate Chemical compound O.OC(=O)C(O)=O.C1CN(C(=O)NCCN(CC)CC)CCN1C1=CC=CC=C1 FMONGVQGMINZKH-UHFFFAOYSA-N 0.000 description 1
- SWGUDYFEQHUHOE-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(2-fluorophenyl)piperazine-1-carboxamide;dihydrochloride Chemical compound Cl.Cl.C1CN(C(=O)NCCN(C)C)CCN1C1=CC=CC=C1F SWGUDYFEQHUHOE-UHFFFAOYSA-N 0.000 description 1
- YTVWGCUDXUOGQT-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(2-fluorophenyl)piperazine-1-carboxamide;hydrate;hydrochloride Chemical compound O.Cl.C1CN(C(=O)NCCN(C)C)CCN1C1=CC=CC=C1F YTVWGCUDXUOGQT-UHFFFAOYSA-N 0.000 description 1
- QKFMACQMXSIXNY-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-(3-fluorophenyl)piperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCN(C)C)CCN1C1=CC=CC(F)=C1 QKFMACQMXSIXNY-UHFFFAOYSA-N 0.000 description 1
- DZJOQCLDFPMFJK-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-4-phenylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCN(C)C)CCN1C1=CC=CC=C1 DZJOQCLDFPMFJK-UHFFFAOYSA-N 0.000 description 1
- GTENIXUBDMTWFS-UHFFFAOYSA-N n-[3-(dimethylamino)propyl]-4-phenylpiperazine-1-carboxamide Chemical compound C1CN(C(=O)NCCCN(C)C)CCN1C1=CC=CC=C1 GTENIXUBDMTWFS-UHFFFAOYSA-N 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000002663 nebulization Methods 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000003891 oxalate salts Chemical class 0.000 description 1
- UNEIHNMKASENIG-UHFFFAOYSA-N para-chlorophenylpiperazine Chemical compound C1=CC(Cl)=CC=C1N1CCNCC1 UNEIHNMKASENIG-UHFFFAOYSA-N 0.000 description 1
- MRDGZSKYFPGAKP-UHFFFAOYSA-N para-methoxyphenylpiperazine Chemical compound C1=CC(OC)=CC=C1N1CCNCC1 MRDGZSKYFPGAKP-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 210000003800 pharynx Anatomy 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- SAALQYKUFCIMHR-UHFFFAOYSA-N propan-2-ol;2-propan-2-yloxypropane Chemical compound CC(C)O.CC(C)OC(C)C SAALQYKUFCIMHR-UHFFFAOYSA-N 0.000 description 1
- XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 206010039083 rhinitis Diseases 0.000 description 1
- 102220004588 rs104893797 Human genes 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000012353 t test Methods 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000009959 type I hypersensitivity Effects 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/215—Radicals derived from nitrogen analogues of carbonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyridine Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/007,592 US4960776A (en) | 1987-01-28 | 1987-01-28 | 4-aryl-N-(alkylaminoalkyl, heterocyclicamino and heterocyclicamino)alkyl)-1-piperazinecarboxamides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO880352D0 NO880352D0 (no) | 1988-01-27 |
| NO880352L true NO880352L (no) | 1988-07-29 |
Family
ID=21727070
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO880352A NO880352L (no) | 1987-01-28 | 1988-01-27 | Fremgangsmaate for fremstilling av 4-aryl-n-(2-(dialkylamino og heterocyklisk amino)alkyl)-1-piperazincarboxamider. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4960776A (fr) |
| EP (1) | EP0277725A3 (fr) |
| JP (1) | JPS63188670A (fr) |
| AU (1) | AU8067687A (fr) |
| DK (1) | DK39988A (fr) |
| FI (1) | FI880371A (fr) |
| IL (1) | IL84045A0 (fr) |
| NO (1) | NO880352L (fr) |
| PT (1) | PT86635B (fr) |
| ZA (1) | ZA877371B (fr) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3719612B2 (ja) * | 1993-06-14 | 2005-11-24 | 塩野義製薬株式会社 | ヘテロ環を含有する尿素誘導体 |
| US5780472A (en) * | 1995-01-11 | 1998-07-14 | Samjin Pharmaceuticazl Co., Ltd. | Piperazine derivatives and methods for the preparation thereof and compositions containing the same |
| US6211199B1 (en) | 1995-11-17 | 2001-04-03 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl-amino)piperidines useful for the treatment of allergic diseases |
| US6194406B1 (en) | 1995-12-20 | 2001-02-27 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic disease |
| US6423704B2 (en) | 1995-12-20 | 2002-07-23 | Aventis Pharmaceuticals Inc. | Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic diseases |
| US5932571A (en) * | 1996-02-21 | 1999-08-03 | Hoechst Marion Roussel, Inc. | Substituted N-methyl-N-(4-(4-(1H-benzimidazol-2-yl) {1,4}diazepan-1-yl)-2-(aryl) butyl) benzamides useful for the treatment of allergic diseases |
| US5998439A (en) | 1996-02-21 | 1999-12-07 | Hoescht Marion Roussel, Inc. | Substituted N-methyl-N-(4-(piperidin-1-yl)-2-(aryl)butyl)benzamides useful for the treatment of allergic diseases |
| US5922737A (en) * | 1996-02-21 | 1999-07-13 | Hoechst Marion Roussel, Inc. | Substituted N-methyl-N-(4-(4-(1H-Benzimidazol-2-YL-amino) piperidin-1-YL)-2-(arlyl) butyl) benzamides useful for the treatment of allergic diseases |
| WO2000063168A1 (fr) * | 1999-04-16 | 2000-10-26 | Coelacanth Chemical Corporation | Synthese de derives d'azetidine |
| GB0421908D0 (en) | 2004-10-01 | 2004-11-03 | Angeletti P Ist Richerche Bio | New uses |
| US8927546B2 (en) | 2006-02-28 | 2015-01-06 | Dart Neuroscience (Cayman) Ltd. | Therapeutic piperazines |
| SG171634A1 (en) | 2006-02-28 | 2011-06-29 | Helicon Therapeutics Inc | Therapeutic piperazines as pde4 inhibitors |
| FR2948369B1 (fr) | 2009-07-27 | 2013-04-12 | Sanofi Aventis | Derives d'uree de tetrahydroquinoxaline, leur preparation et leur application en therapeutique |
| FR2948370B1 (fr) | 2009-07-27 | 2013-04-05 | Sanofi Aventis | Derives d'uree de tetrahydroquinoxaline, leur preparation et leur application en therapeutique |
| US10689360B1 (en) * | 2019-01-30 | 2020-06-23 | Insilico Medicine Ip Limited | TLR inhibitors |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2642255A (en) * | 1947-12-10 | 1953-06-16 | Weatherhead Co | Packless valve |
| US3133067A (en) * | 1959-01-30 | 1964-05-12 | Sterling Drug Inc | 1-monocarbocyclic aryl-4-thiocarbam-ylpiperazines and intermediates and processes therefor |
| NO154582C (no) * | 1978-10-20 | 1986-11-05 | Ferrosan Ab | Analogifremgangsmaate for fremstilling av terapeutisk aktive difenyl-dibutylpiperazinkarboksamider. |
| JPS56127370A (en) * | 1980-02-15 | 1981-10-06 | Mitsui Toatsu Chem Inc | Novel piperazine compound, its preparation and utilization |
| US4593102A (en) * | 1984-04-10 | 1986-06-03 | A. H. Robins Company, Inc. | N-[(amino)alkyl]-1-pyrrolidine, 1-piperidine and 1-homopiperidinecarboxamides (and thiocarboxamides) with sulfur linked substitution in the 2, 3 or 4-position |
| DE3420193A1 (de) * | 1984-05-30 | 1985-12-05 | Boehringer Ingelheim KG, 6507 Ingelheim | Neue substituierte pyrrolidinone, verfahren zu ihrer herstellung und arzneimittel |
| US4594343A (en) * | 1984-10-19 | 1986-06-10 | Shanklin Jr James R | 1-[(aminoalkyl and aminoalkylamino)carbonyl and thiocarbonyl]-α,α-diarylpyrrolidine, piperidine and homopiperidineacetamides and acetonitriles |
-
1987
- 1987-01-28 US US07/007,592 patent/US4960776A/en not_active Expired - Fee Related
- 1987-09-30 IL IL84045A patent/IL84045A0/xx unknown
- 1987-09-30 ZA ZA877371A patent/ZA877371B/xx unknown
- 1987-11-04 AU AU80676/87A patent/AU8067687A/en not_active Abandoned
- 1987-11-11 JP JP62285156A patent/JPS63188670A/ja active Pending
-
1988
- 1988-01-20 EP EP88300436A patent/EP0277725A3/fr not_active Withdrawn
- 1988-01-27 FI FI880371A patent/FI880371A/fi not_active IP Right Cessation
- 1988-01-27 NO NO880352A patent/NO880352L/no unknown
- 1988-01-27 PT PT86635A patent/PT86635B/pt not_active IP Right Cessation
- 1988-01-27 DK DK039988A patent/DK39988A/da not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US4960776A (en) | 1990-10-02 |
| EP0277725A2 (fr) | 1988-08-10 |
| AU8067687A (en) | 1988-08-04 |
| IL84045A0 (en) | 1988-02-29 |
| NO880352D0 (no) | 1988-01-27 |
| FI880371A0 (fi) | 1988-01-27 |
| PT86635A (pt) | 1988-02-01 |
| DK39988A (da) | 1988-07-29 |
| PT86635B (pt) | 1992-01-31 |
| DK39988D0 (da) | 1988-01-27 |
| FI880371A (fi) | 1988-07-29 |
| JPS63188670A (ja) | 1988-08-04 |
| EP0277725A3 (fr) | 1988-08-31 |
| ZA877371B (en) | 1988-04-11 |
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