CH643549A5 - N-(trimethoxybenzyl)-n'-phenylpiperazine. - Google Patents
N-(trimethoxybenzyl)-n'-phenylpiperazine. Download PDFInfo
- Publication number
- CH643549A5 CH643549A5 CH622980A CH622980A CH643549A5 CH 643549 A5 CH643549 A5 CH 643549A5 CH 622980 A CH622980 A CH 622980A CH 622980 A CH622980 A CH 622980A CH 643549 A5 CH643549 A5 CH 643549A5
- Authority
- CH
- Switzerland
- Prior art keywords
- trimethoxybenzyl
- alkoxy
- formula
- alkyl
- piperazine
- Prior art date
Links
- NIQFIUZYSBPAKU-UHFFFAOYSA-N 1-[dimethoxy-(2-methoxyphenyl)methyl]-4-phenylpiperazine Chemical compound COC1=CC=CC=C1C(OC)(OC)N1CCN(C=2C=CC=CC=2)CC1 NIQFIUZYSBPAKU-UHFFFAOYSA-N 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 29
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- -1 3,4,5-trimethoxybenzyl halide Chemical class 0.000 claims description 15
- 150000002367 halogens Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 239000004480 active ingredient Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- YUPUSBMJCFBHAP-UHFFFAOYSA-N (3,4,5-trimethoxyphenyl)methanamine Chemical compound COC1=CC(CN)=CC(OC)=C1OC YUPUSBMJCFBHAP-UHFFFAOYSA-N 0.000 claims description 9
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical compound C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- MWNCHGVMCXDYED-UHFFFAOYSA-N 1-(2-methylphenyl)-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine Chemical compound COC1=C(OC)C(OC)=CC(CN2CCN(CC2)C=2C(=CC=CC=2)C)=C1 MWNCHGVMCXDYED-UHFFFAOYSA-N 0.000 claims description 2
- LMOGEOIHIWFDKE-UHFFFAOYSA-N 1-(2-ethoxyphenyl)-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine Chemical compound CCOC1=CC=CC=C1N1CCN(CC=2C=C(OC)C(OC)=C(OC)C=2)CC1 LMOGEOIHIWFDKE-UHFFFAOYSA-N 0.000 claims 1
- JOIWQEYNQUFQNE-UHFFFAOYSA-N 1-(2-ethylphenyl)-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine Chemical compound CCC1=CC=CC=C1N1CCN(CC=2C=C(OC)C(OC)=C(OC)C=2)CC1 JOIWQEYNQUFQNE-UHFFFAOYSA-N 0.000 claims 1
- JNWYVRLAZGEFRB-UHFFFAOYSA-N 1-(3-methoxyphenyl)-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine Chemical compound COC1=CC=CC(N2CCN(CC=3C=C(OC)C(OC)=C(OC)C=3)CC2)=C1 JNWYVRLAZGEFRB-UHFFFAOYSA-N 0.000 claims 1
- KKCOGNFFBYOKMA-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine Chemical compound COC1=C(OC)C(OC)=CC(CN2CCN(CC2)C=2C=CC(F)=CC=2)=C1 KKCOGNFFBYOKMA-UHFFFAOYSA-N 0.000 claims 1
- 238000002844 melting Methods 0.000 description 20
- 230000008018 melting Effects 0.000 description 20
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 19
- XXRUQNNAKXZSOS-UHFFFAOYSA-N 5-(chloromethyl)-1,2,3-trimethoxybenzene Chemical compound COC1=CC(CCl)=CC(OC)=C1OC XXRUQNNAKXZSOS-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229910000027 potassium carbonate Inorganic materials 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- 230000002792 vascular Effects 0.000 description 11
- DERZBLKQOCDDDZ-JLHYYAGUSA-N cinnarizine Chemical compound C1CN(C(C=2C=CC=CC=2)C=2C=CC=CC=2)CCN1C\C=C\C1=CC=CC=C1 DERZBLKQOCDDDZ-JLHYYAGUSA-N 0.000 description 10
- 229960000876 cinnarizine Drugs 0.000 description 10
- 229910052731 fluorine Inorganic materials 0.000 description 10
- 239000011737 fluorine Substances 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000007789 gas Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- 150000004885 piperazines Chemical class 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000008107 starch Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000003840 hydrochlorides Chemical class 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- RHQQHZQUAMFINJ-GKWSUJDHSA-N 1-[(3s,5s,8s,9s,10s,11s,13s,14s,17s)-3,11-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-hydroxyethanone Chemical compound C1[C@@H](O)CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CC[C@H]21 RHQQHZQUAMFINJ-GKWSUJDHSA-N 0.000 description 2
- 125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 231100000403 acute toxicity Toxicity 0.000 description 2
- 230000007059 acute toxicity Effects 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 2
- 229940038472 dicalcium phosphate Drugs 0.000 description 2
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- CVVIJWRCGSYCMB-UHFFFAOYSA-N hydron;piperazine;dichloride Chemical compound Cl.Cl.C1CNCCN1 CVVIJWRCGSYCMB-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000013558 reference substance Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QNCWKECHSBDMPF-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)piperazine Chemical compound C1=C2OCOC2=CC=C1N1CCNCC1 QNCWKECHSBDMPF-UHFFFAOYSA-N 0.000 description 1
- ZDUKNPPJJCLUBH-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CN2CCN(CC2)C=2C(=CC=CC=2C)C)=C1 ZDUKNPPJJCLUBH-UHFFFAOYSA-N 0.000 description 1
- JDVUSTNITSGJOH-UHFFFAOYSA-N 1-(2,6-dimethylphenyl)piperazine Chemical compound CC1=CC=CC(C)=C1N1CCNCC1 JDVUSTNITSGJOH-UHFFFAOYSA-N 0.000 description 1
- ZMONCZQGFUAONA-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine Chemical compound COC1=C(OC)C(OC)=CC(CN2CCN(CC2)C=2C(=CC=CC=2)Cl)=C1 ZMONCZQGFUAONA-UHFFFAOYSA-N 0.000 description 1
- PWZDJIUQHUGFRJ-UHFFFAOYSA-N 1-(2-chlorophenyl)piperazine Chemical compound ClC1=CC=CC=C1N1CCNCC1 PWZDJIUQHUGFRJ-UHFFFAOYSA-N 0.000 description 1
- UMBOIQPCUXFUFZ-UHFFFAOYSA-N 1-(2-ethoxyphenyl)-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine;dihydrochloride Chemical compound Cl.Cl.CCOC1=CC=CC=C1N1CCN(CC=2C=C(OC)C(OC)=C(OC)C=2)CC1 UMBOIQPCUXFUFZ-UHFFFAOYSA-N 0.000 description 1
- FBQIUSDQWOLCNY-UHFFFAOYSA-N 1-(2-ethoxyphenyl)piperazine Chemical compound CCOC1=CC=CC=C1N1CCNCC1 FBQIUSDQWOLCNY-UHFFFAOYSA-N 0.000 description 1
- NXRLQKQALWFYAK-UHFFFAOYSA-N 1-(2-ethylphenyl)-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine;dihydrochloride Chemical compound Cl.Cl.CCC1=CC=CC=C1N1CCN(CC=2C=C(OC)C(OC)=C(OC)C=2)CC1 NXRLQKQALWFYAK-UHFFFAOYSA-N 0.000 description 1
- GFFQZPFWQJWGBK-UHFFFAOYSA-N 1-(2-fluorophenyl)-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CN2CCN(CC2)C=2C(=CC=CC=2)F)=C1 GFFQZPFWQJWGBK-UHFFFAOYSA-N 0.000 description 1
- JDVIUHLPZGWPQV-UHFFFAOYSA-N 1-(2-methoxyphenyl)-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine;dihydrochloride Chemical compound Cl.Cl.COC1=CC=CC=C1N1CCN(CC=2C=C(OC)C(OC)=C(OC)C=2)CC1 JDVIUHLPZGWPQV-UHFFFAOYSA-N 0.000 description 1
- VNZLQLYBRIOLFZ-UHFFFAOYSA-N 1-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCNCC1 VNZLQLYBRIOLFZ-UHFFFAOYSA-N 0.000 description 1
- WICKLEOONJPMEQ-UHFFFAOYSA-N 1-(2-methylphenyl)piperazine Chemical compound CC1=CC=CC=C1N1CCNCC1 WICKLEOONJPMEQ-UHFFFAOYSA-N 0.000 description 1
- GZDUUSZPKIEBDM-UHFFFAOYSA-N 1-(2-nitrophenyl)-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CN2CCN(CC2)C=2C(=CC=CC=2)[N+]([O-])=O)=C1 GZDUUSZPKIEBDM-UHFFFAOYSA-N 0.000 description 1
- QSTMOHFZTDLSBZ-UHFFFAOYSA-N 1-(3,4,5-trimethoxyphenyl)piperazine Chemical compound COC1=C(OC)C(OC)=CC(N2CCNCC2)=C1 QSTMOHFZTDLSBZ-UHFFFAOYSA-N 0.000 description 1
- AKQHQKRWLCVIPU-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CN2CCN(CC2)C=2C=C(C)C(C)=CC=2)=C1 AKQHQKRWLCVIPU-UHFFFAOYSA-N 0.000 description 1
- SFLNVAVCCYTHCQ-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)piperazine Chemical compound C1=C(C)C(C)=CC=C1N1CCNCC1 SFLNVAVCCYTHCQ-UHFFFAOYSA-N 0.000 description 1
- UYZOZSNGFPGQPV-UHFFFAOYSA-N 1-(3-methoxyphenyl)-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine;hydrochloride Chemical compound Cl.COC1=CC=CC(N2CCN(CC=3C=C(OC)C(OC)=C(OC)C=3)CC2)=C1 UYZOZSNGFPGQPV-UHFFFAOYSA-N 0.000 description 1
- PZIBVWUXWNYTNL-UHFFFAOYSA-N 1-(3-methoxyphenyl)piperazine Chemical compound COC1=CC=CC(N2CCNCC2)=C1 PZIBVWUXWNYTNL-UHFFFAOYSA-N 0.000 description 1
- PSBVPOHSKOPVQO-UHFFFAOYSA-N 1-(3-methylphenyl)-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CN2CCN(CC2)C=2C=C(C)C=CC=2)=C1 PSBVPOHSKOPVQO-UHFFFAOYSA-N 0.000 description 1
- VBEFHINCTCYNJA-UHFFFAOYSA-N 1-(4-fluorophenyl)-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CN2CCN(CC2)C=2C=CC(F)=CC=2)=C1 VBEFHINCTCYNJA-UHFFFAOYSA-N 0.000 description 1
- IECVYJWQLCJEEL-UHFFFAOYSA-N 1-(4-methoxyphenyl)-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine;dihydrochloride Chemical compound Cl.Cl.C1=CC(OC)=CC=C1N1CCN(CC=2C=C(OC)C(OC)=C(OC)C=2)CC1 IECVYJWQLCJEEL-UHFFFAOYSA-N 0.000 description 1
- ZGBURIAEMYVQBZ-UHFFFAOYSA-N 1-(4-methylphenyl)-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CN2CCN(CC2)C=2C=CC(C)=CC=2)=C1 ZGBURIAEMYVQBZ-UHFFFAOYSA-N 0.000 description 1
- VHCJPRZEACGXJW-UHFFFAOYSA-N 1-[3,5-bis(trifluoromethyl)phenyl]-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CN2CCN(CC2)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 VHCJPRZEACGXJW-UHFFFAOYSA-N 0.000 description 1
- LUIPVTMUUVKHKV-UHFFFAOYSA-N 1-[4-chloro-3-(trifluoromethyl)phenyl]-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CN2CCN(CC2)C=2C=C(C(Cl)=CC=2)C(F)(F)F)=C1 LUIPVTMUUVKHKV-UHFFFAOYSA-N 0.000 description 1
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical class C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- GXOVGAABWPQKTP-UHFFFAOYSA-N 1-phenyl-4-[(3,4,5-trimethoxyphenyl)methyl]piperazine;hydrochloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CN2CCN(CC2)C=2C=CC=CC=2)=C1 GXOVGAABWPQKTP-UHFFFAOYSA-N 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- RHEJPBFFJBKULZ-UHFFFAOYSA-N 4-chloro-n,n-bis(2-chloroethyl)-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N(CCCl)CCCl)=CC=C1Cl RHEJPBFFJBKULZ-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- GPEOAEVZTOQXLG-UHFFFAOYSA-N 4-piperazin-1-ium-1-ylphenolate Chemical compound C1=CC(O)=CC=C1N1CCNCC1 GPEOAEVZTOQXLG-UHFFFAOYSA-N 0.000 description 1
- QSXCPLAFNLQCBL-UHFFFAOYSA-N 5-(chloromethyl)-1,2,3-trimethylbenzene Chemical compound CC1=CC(CCl)=CC(C)=C1C QSXCPLAFNLQCBL-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 244000144725 Amygdalus communis Species 0.000 description 1
- 235000011437 Amygdalus communis Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZUWCJVUSVPUJIM-UHFFFAOYSA-N C(C)OClO Chemical compound C(C)OClO ZUWCJVUSVPUJIM-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 244000131522 Citrus pyriformis Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000000159 acid neutralizing agent Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 231100000215 acute (single dose) toxicity testing Toxicity 0.000 description 1
- 231100000460 acute oral toxicity Toxicity 0.000 description 1
- 238000011047 acute toxicity test Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000002908 adrenolytic effect Effects 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 235000020224 almond Nutrition 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 230000036770 blood supply Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000005998 bromoethyl group Chemical group 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000003979 granulating agent Substances 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000014380 magnesium carbonate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-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
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- JZWFDVDETGFGFC-UHFFFAOYSA-N salacetamide Chemical group CC(=O)NC(=O)C1=CC=CC=C1O JZWFDVDETGFGFC-UHFFFAOYSA-N 0.000 description 1
- 229940125723 sedative agent Drugs 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 229940066771 systemic antihistamines piperazine derivative Drugs 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000001701 trimethoxybenzyl group Chemical group 0.000 description 1
Classifications
-
- 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
- C07D295/04—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—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 with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2934488A DE2934488C2 (de) | 1979-08-25 | 1979-08-25 | N-(Trimethoxybenzyl)-N'-(einfachsubstituierte-phenyl)-piperazine, deren Salze, Verfahren zu deren Herstellung und Arzneimittel |
| DE19792934450 DE2934450C2 (de) | 1979-08-25 | 1979-08-25 | N-(Trimethoxybenzyl)-piperazinderivate und deren Salze, Verfahren zu deren Herstellung und Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH643549A5 true CH643549A5 (de) | 1984-06-15 |
Family
ID=25780725
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH622980A CH643549A5 (de) | 1979-08-25 | 1980-08-18 | N-(trimethoxybenzyl)-n'-phenylpiperazine. |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US4370329A (show.php) |
| AT (1) | AT375075B (show.php) |
| AU (1) | AU538005B2 (show.php) |
| CA (1) | CA1153377A (show.php) |
| CH (1) | CH643549A5 (show.php) |
| DK (1) | DK363280A (show.php) |
| ES (1) | ES8104264A1 (show.php) |
| FR (1) | FR2463768A1 (show.php) |
| GB (1) | GB2057441B (show.php) |
| GR (1) | GR69917B (show.php) |
| HU (1) | HU182180B (show.php) |
| IL (1) | IL60891A (show.php) |
| MX (1) | MX6163E (show.php) |
| NL (1) | NL8004783A (show.php) |
| PL (1) | PL125663B1 (show.php) |
| SE (1) | SE8005943L (show.php) |
| SG (1) | SG3385G (show.php) |
| YU (1) | YU211480A (show.php) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4713382A (en) * | 1985-05-30 | 1987-12-15 | Syntex (U.S.A.) Inc. | N-phenyl-4-phenyl-1-piperazinecarboxamidines and related compounds as antiarrhythmic agents |
| IL85700A0 (en) * | 1987-03-24 | 1988-08-31 | Takeda Chemical Industries Ltd | 1,4-disubstituted piperazine compounds,their production and use |
| DE3715763A1 (de) * | 1987-05-12 | 1988-11-24 | Hoechst Ag | Diarylalkyl-substituierte alkylamine, verfahren zu ihrer herstellung, ihre verwendung sowie sie enthaltende arzneimittel |
| US5346653A (en) * | 1991-02-18 | 1994-09-13 | Matsushita Electric Industrial Co., Ltd. | Non-linear optical material, method of manufacturing the same and optical wavelength converter |
| WO1997041108A1 (en) * | 1996-04-30 | 1997-11-06 | Warner-Lambert Company | Substituted piperazines and piperidines as central nervous system agents |
| HUP9601331A3 (en) * | 1996-05-17 | 2000-06-28 | Egyt Gyogyszervegyeszeti Gyar | Piperazine- and homopiperazine-derivatives, process for producing them and pharmaceutical compositions containing them |
| US5859246A (en) * | 1997-01-30 | 1999-01-12 | Neurogen Corporation | 1-phenyl-4-benzylpiperazines: dopamine receptor subtype specific ligands |
| MXPA03000174A (es) | 2000-07-06 | 2003-09-22 | Neurogen Corp | Ligandos de receptor de hormona concentradora de melanina. |
| EP1389189A2 (en) * | 2001-05-22 | 2004-02-18 | Neurogen Corporation | Melanin concentrating hormone receptor ligands: substituted 1-benzyl-4-aryl piperazine analogues |
| RU2260431C2 (ru) * | 2003-12-15 | 2005-09-20 | Закрытое акционерное общество "Фармацевтическое предприятие "Оболенское" | Лекарственная форма, обладающая антиангинальным действием, и способ ее изготовления |
| WO2005110989A1 (en) * | 2004-04-07 | 2005-11-24 | Neurogen Corporation | Substituted 1-heteroaryl-4-substituted piperazine and piperidine analogues |
| WO2005110982A2 (en) * | 2004-04-07 | 2005-11-24 | Neurogen Corporation | Substituted 1-benzyl-4-substituted piperazine analogues |
| TW200609219A (en) * | 2004-06-17 | 2006-03-16 | Neurogen Corp | Aryl-substituted piperazine derivatives |
| RU2281772C1 (ru) * | 2005-02-14 | 2006-08-20 | Закрытое акционерное общество "Фармацевтическое предприятие "Оболенское" | Лекарственная форма, обладающая антиангинальным действием, и способ ее изготовления |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB868353A (en) | 1959-12-01 | 1961-05-17 | Soc Ind Fab Antibiotiques Sifa | Phenyl piperazine derivatives for therapeutic use and processes for the production of such derivatives |
| FR1275308A (fr) * | 1960-11-30 | 1961-11-03 | Soc Ind Fab Antibiotiques Sifa | Nouveaux dérivés de la phényl pipérazine, et leur préparation |
| GB939822A (en) * | 1961-03-29 | 1963-10-16 | Soc Ind Fab Antibiotiques Sifa | Piperazine compounds |
| US4100285A (en) | 1976-04-09 | 1978-07-11 | Nippon Shinyaku Co., Ltd. | N-substituted trialkoxybenzyl piperazine derivatives |
-
1980
- 1980-08-18 CH CH622980A patent/CH643549A5/de not_active IP Right Cessation
- 1980-08-19 AT AT0423080A patent/AT375075B/de active
- 1980-08-21 IL IL60891A patent/IL60891A/xx unknown
- 1980-08-22 FR FR8018407A patent/FR2463768A1/fr active Granted
- 1980-08-22 HU HU802091A patent/HU182180B/hu unknown
- 1980-08-22 DK DK363280A patent/DK363280A/da not_active Application Discontinuation
- 1980-08-22 MX MX808987U patent/MX6163E/es unknown
- 1980-08-22 ES ES494426A patent/ES8104264A1/es not_active Expired
- 1980-08-22 US US06/181,189 patent/US4370329A/en not_active Expired - Lifetime
- 1980-08-22 GB GB8027405A patent/GB2057441B/en not_active Expired
- 1980-08-24 NL NL8004783A patent/NL8004783A/nl not_active Application Discontinuation
- 1980-08-25 CA CA000358914A patent/CA1153377A/en not_active Expired
- 1980-08-25 AU AU61719/80A patent/AU538005B2/en not_active Ceased
- 1980-08-25 GR GR62738A patent/GR69917B/el unknown
- 1980-08-25 PL PL1980226396A patent/PL125663B1/pl unknown
- 1980-08-25 YU YU02114/80A patent/YU211480A/xx unknown
- 1980-08-25 SE SE8005943A patent/SE8005943L/xx not_active Application Discontinuation
-
1981
- 1981-10-05 US US06/308,607 patent/US4370330A/en not_active Expired - Fee Related
-
1985
- 1985-01-11 SG SG33/85A patent/SG3385G/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU6171980A (en) | 1981-03-05 |
| PL125663B1 (en) | 1983-06-30 |
| HU182180B (en) | 1983-12-28 |
| GB2057441A (en) | 1981-04-01 |
| DK363280A (da) | 1981-02-26 |
| US4370329A (en) | 1983-01-25 |
| US4370330A (en) | 1983-01-25 |
| NL8004783A (nl) | 1981-02-27 |
| FR2463768B1 (show.php) | 1983-11-25 |
| ATA423080A (de) | 1983-11-15 |
| GB2057441B (en) | 1983-05-25 |
| SE8005943L (sv) | 1981-02-26 |
| SG3385G (en) | 1985-06-14 |
| YU211480A (en) | 1983-06-30 |
| AU538005B2 (en) | 1984-07-26 |
| AT375075B (de) | 1984-06-25 |
| PL226396A1 (show.php) | 1981-10-30 |
| ES494426A0 (es) | 1981-04-01 |
| IL60891A (en) | 1984-03-30 |
| MX6163E (es) | 1984-11-29 |
| ES8104264A1 (es) | 1981-04-01 |
| CA1153377A (en) | 1983-09-06 |
| FR2463768A1 (fr) | 1981-02-27 |
| IL60891A0 (en) | 1980-10-26 |
| GR69917B (show.php) | 1982-07-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1643262C3 (de) | i-Phenoxy^-hydroxy-S-alklyaminopropane, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| EP0005828B1 (de) | Neue substituierte Phenylpiperazinderivate, diese enthaltende Arzneimittel und Verfahren zu deren Herstellung | |
| CH643549A5 (de) | N-(trimethoxybenzyl)-n'-phenylpiperazine. | |
| DE2415082A1 (de) | Disubstituierte piperazine, verfahren zu deren herstellung und diese verbindungen enthaltende arzneimittel | |
| DE2502397A1 (de) | Guanidinderivate, ein verfahren zu deren herstellung sowie arzneimittel | |
| EP0101574A1 (de) | 2-Substituierte 1-Aminoalkyl-1,2,3,4-tetrahydro-beta-carboline, ihre Herstellung und Verwendung als Arzneimittel | |
| EP0303951B1 (de) | 2-Pyrimidinyl-1-piperazin-Derivate zur Behandlung von Alkoholismus | |
| EP0105210B1 (de) | Isochinolinderivate, Verfahren zu ihrer Herstellung, pharmazeutische Präparate auf Basis dieser Verbindungen und ihre Verwendung | |
| DE2523103A1 (de) | Neue propargyl-2-phenylamino-imidazoline-(2), deren saeureadditionssalze, diese enthaltende arzneimittel und verfahren zur herstellung derselben | |
| EP0435902B1 (de) | 2-hydroxy-3-phenoxy-propyl-substituierte piperazine, ihre herstellung und verwendung | |
| DE1901519A1 (de) | Chinazolinylharnstoffe | |
| DE2231067A1 (de) | Phenoxathiinderivate mit antiviraler wirkung, verfahren zu ihrer herstellung sowie pharmazeutische praeparate mit einem gehalt an phenoxathiinderivaten | |
| CH645368A5 (de) | 2-hydroxy-5-(1-hydroxy-2-piperazinylethyl)benzoesaeure-derivate sowie verfahren zu deren herstellung. | |
| EP0075165B1 (de) | 9,10-Substituierte 2-Mesitylimino-3-alkyl-3,4,6,7-tetrahydro-2H-pyrimido(6,1-a)isochinolin-4-one, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel | |
| DE2062055C3 (de) | Propanolamin-Derivate, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel | |
| DE2034640A1 (de) | p (Tnhalogenmethylchinolylamino) benzamide und Verfahren zu ihrer Her stellung | |
| AT376965B (de) | Verfahren zum herstellen von neuen n-(trimethoxybenzyl)-n'-phenylpiperazinen und ihren saeureadditionssalzen | |
| DE2435816B2 (de) | Substituierte nitrobenzophenonderivate, ihre salze, verfahren zur herstellung derselben und arzneimittel | |
| DE2442158A1 (de) | Neue substituierte n- eckige klammer auf l-(3,4-methylendioxyphenyl)propyl(2) eckige klammer zu -n'-subst. phenylpiperazine | |
| DE3116250A1 (de) | "nonaprenylamin-derivate und sie enthaltende pharmazeutische mittel" | |
| DE69523346T2 (de) | Substituierte 6-h-1,3,4-thiadiazin-2-amine, deren verwendung als anaesthetisierende cardiovaskulare und hypometabole mittel, und eine sie enthaltende pharmazeutische zubereitung | |
| DE2525725A1 (de) | Substituierte 4-phenyl-imidazoline, deren saeureadditionssalze und verfahren zu ihrer herstellung | |
| DE2934450C2 (de) | N-(Trimethoxybenzyl)-piperazinderivate und deren Salze, Verfahren zu deren Herstellung und Arzneimittel | |
| DE2934488C2 (de) | N-(Trimethoxybenzyl)-N'-(einfachsubstituierte-phenyl)-piperazine, deren Salze, Verfahren zu deren Herstellung und Arzneimittel | |
| DE1958212A1 (de) | Neue substituierte N-Cycloalkyl-arylamino-imidazoline-(2) und Verfahren zu deren Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |