HU176820B - Process for preparing phenyl-piperazine derivatives - Google Patents
Process for preparing phenyl-piperazine derivatives Download PDFInfo
- Publication number
- HU176820B HU176820B HU77LI311A HULI000311A HU176820B HU 176820 B HU176820 B HU 176820B HU 77LI311 A HU77LI311 A HU 77LI311A HU LI000311 A HULI000311 A HU LI000311A HU 176820 B HU176820 B HU 176820B
- Authority
- HU
- Hungary
- Prior art keywords
- phenyl
- formula
- piperazine
- ylmethyl
- compound
- Prior art date
Links
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 85
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 43
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- 238000002360 preparation method Methods 0.000 claims abstract description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 238000009833 condensation Methods 0.000 claims abstract 2
- 230000005494 condensation Effects 0.000 claims abstract 2
- -1 hydroxy, nitro, amino Chemical group 0.000 claims description 61
- 238000000034 method Methods 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 239000007858 starting material Substances 0.000 claims description 12
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
- 206010029897 Obsessive thoughts Diseases 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 229920000137 polyphosphoric acid Polymers 0.000 claims description 5
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- BAEORBQOPCVJAH-UHFFFAOYSA-N 2-benzyl-4-[(4-phenylpiperazin-1-yl)methyl]-1,3-thiazole Chemical compound C=1SC(CC=2C=CC=CC=2)=NC=1CN(CC1)CCN1C1=CC=CC=C1 BAEORBQOPCVJAH-UHFFFAOYSA-N 0.000 claims description 4
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000005557 thiazolylene group Chemical group 0.000 claims description 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
- OBQYFPBESLPHHK-UHFFFAOYSA-N 2-benzyl-4-(chloromethyl)-1,3-thiazole Chemical compound ClCC1=CSC(CC=2C=CC=CC=2)=N1 OBQYFPBESLPHHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 3
- 125000005564 oxazolylene group Chemical group 0.000 claims description 3
- 125000005730 thiophenylene group Chemical group 0.000 claims description 3
- 150000001450 anions Chemical class 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 125000004803 chlorobenzyl group Chemical group 0.000 claims description 2
- 239000012024 dehydrating agents Substances 0.000 claims description 2
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract description 4
- 208000006673 asthma Diseases 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 241000124008 Mammalia Species 0.000 abstract 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 abstract 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 230000000069 prophylactic effect Effects 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 abstract 1
- 229930192474 thiophene Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 47
- 239000000243 solution Substances 0.000 description 43
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- 238000003756 stirring Methods 0.000 description 20
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000003921 oil Substances 0.000 description 15
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000284 extract Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000003610 charcoal Substances 0.000 description 7
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000003826 tablet Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- JJDXREXQSCIIJY-UHFFFAOYSA-N (2-amino-2-sulfanylideneethyl) acetate Chemical compound CC(=O)OCC(N)=S JJDXREXQSCIIJY-UHFFFAOYSA-N 0.000 description 3
- TYUWZKSJURGPRJ-UHFFFAOYSA-N (4-phenyl-1,3-thiazol-2-yl)methanol Chemical compound S1C(CO)=NC(C=2C=CC=CC=2)=C1 TYUWZKSJURGPRJ-UHFFFAOYSA-N 0.000 description 3
- FHBNFEHLTZSQOR-UHFFFAOYSA-N 1-(3-chlorophenyl)-4-[(5-phenylthiophen-2-yl)methyl]piperazine Chemical compound ClC1=CC=CC(N2CCN(CC=3SC(=CC=3)C=3C=CC=CC=3)CC2)=C1 FHBNFEHLTZSQOR-UHFFFAOYSA-N 0.000 description 3
- DJKMAJBJDYWGIS-UHFFFAOYSA-N 1-(5-phenylfuran-2-yl)propan-2-ol Chemical compound O1C(CC(O)C)=CC=C1C1=CC=CC=C1 DJKMAJBJDYWGIS-UHFFFAOYSA-N 0.000 description 3
- HTGUJDLBZUXWFC-UHFFFAOYSA-N 1-[[5-(3,4-dimethylphenyl)furan-2-yl]methyl]-4-phenylpiperazine Chemical compound C1=C(C)C(C)=CC=C1C(O1)=CC=C1CN1CCN(C=2C=CC=CC=2)CC1 HTGUJDLBZUXWFC-UHFFFAOYSA-N 0.000 description 3
- FCXHZNGCMZFMLB-UHFFFAOYSA-N 1-phenyl-4-[(5-phenylthiophen-2-yl)methyl]piperazine Chemical compound C=1C=C(C=2C=CC=CC=2)SC=1CN(CC1)CCN1C1=CC=CC=C1 FCXHZNGCMZFMLB-UHFFFAOYSA-N 0.000 description 3
- GEKGXUITXYAIED-UHFFFAOYSA-N 1-phenyl-4-[2-(5-phenylthiophen-2-yl)ethyl]piperazine Chemical compound C1CN(C=2C=CC=CC=2)CCN1CCC(S1)=CC=C1C1=CC=CC=C1 GEKGXUITXYAIED-UHFFFAOYSA-N 0.000 description 3
- RDOBRNOEPGSNQE-UHFFFAOYSA-N 2-(5-phenylthiophen-2-yl)ethanol Chemical compound S1C(CCO)=CC=C1C1=CC=CC=C1 RDOBRNOEPGSNQE-UHFFFAOYSA-N 0.000 description 3
- YBGXWDOUCLDSBT-UHFFFAOYSA-N 2-(bromomethyl)-5-[3-(trifluoromethyl)phenyl]furan Chemical compound FC(F)(F)C1=CC=CC(C=2OC(CBr)=CC=2)=C1 YBGXWDOUCLDSBT-UHFFFAOYSA-N 0.000 description 3
- FQSDPNWLPHANMB-UHFFFAOYSA-N 2-chloro-n-phenacylacetamide Chemical compound ClCC(=O)NCC(=O)C1=CC=CC=C1 FQSDPNWLPHANMB-UHFFFAOYSA-N 0.000 description 3
- XRFWDWNOUYIGGY-UHFFFAOYSA-N 3-bromo-n-phenacylpropanamide Chemical compound BrCCC(=O)NCC(=O)C1=CC=CC=C1 XRFWDWNOUYIGGY-UHFFFAOYSA-N 0.000 description 3
- KSHWYDGWGVFSJR-UHFFFAOYSA-N 4-[4-[(5-phenyl-1,3-oxazol-2-yl)methyl]piperazin-1-yl]aniline Chemical compound C1=CC(N)=CC=C1N1CCN(CC=2OC(=CN=2)C=2C=CC=CC=2)CC1 KSHWYDGWGVFSJR-UHFFFAOYSA-N 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 3
- TUFYTBLUQVDMST-UHFFFAOYSA-N 4-phenyl-2-[(4-phenylpiperazin-1-yl)methyl]-1,3-thiazole Chemical compound N=1C(C=2C=CC=CC=2)=CSC=1CN(CC1)CCN1C1=CC=CC=C1 TUFYTBLUQVDMST-UHFFFAOYSA-N 0.000 description 3
- VTOQRROVVPDIIF-UHFFFAOYSA-N 5-phenyl-2-[(4-phenylpiperazin-1-yl)methyl]-1,3-oxazole Chemical compound N=1C=C(C=2C=CC=CC=2)OC=1CN(CC1)CCN1C1=CC=CC=C1 VTOQRROVVPDIIF-UHFFFAOYSA-N 0.000 description 3
- NSKIAVMDKCAZIK-UHFFFAOYSA-N 5-phenyl-2-[2-(4-phenylpiperazin-1-yl)ethyl]-1,3-oxazole Chemical compound C1CN(C=2C=CC=CC=2)CCN1CCC(O1)=NC=C1C1=CC=CC=C1 NSKIAVMDKCAZIK-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229920000168 Microcrystalline cellulose Polymers 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- XPXRIFIZAIPZDF-UHFFFAOYSA-N [5-[3-(trifluoromethyl)phenyl]furan-2-yl]methanol Chemical compound O1C(CO)=CC=C1C1=CC=CC(C(F)(F)F)=C1 XPXRIFIZAIPZDF-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 150000001805 chlorine compounds Chemical class 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229940057995 liquid paraffin Drugs 0.000 description 3
- 239000008108 microcrystalline cellulose Substances 0.000 description 3
- 229940016286 microcrystalline cellulose Drugs 0.000 description 3
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000003380 propellant Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- SUNMBRGCANLOEG-UHFFFAOYSA-N 1,3-dichloroacetone Chemical compound ClCC(=O)CCl SUNMBRGCANLOEG-UHFFFAOYSA-N 0.000 description 2
- QMIVBPXNYLQQKP-UHFFFAOYSA-N 1-(3,4-dimethylphenyl)-4-[(5-phenylthiophen-2-yl)methyl]piperazine Chemical compound C1=C(C)C(C)=CC=C1N1CCN(CC=2SC(=CC=2)C=2C=CC=CC=2)CC1 QMIVBPXNYLQQKP-UHFFFAOYSA-N 0.000 description 2
- DOYNABJKDZARLF-UHFFFAOYSA-N 1-(3-bromophenyl)piperazine Chemical compound BrC1=CC=CC(N2CCNCC2)=C1 DOYNABJKDZARLF-UHFFFAOYSA-N 0.000 description 2
- SSASWPMHNMYMLZ-UHFFFAOYSA-N 1-(4-methylphenyl)-4-[(5-phenylfuran-2-yl)methyl]piperazine Chemical compound C1=CC(C)=CC=C1N1CCN(CC=2OC(=CC=2)C=2C=CC=CC=2)CC1 SSASWPMHNMYMLZ-UHFFFAOYSA-N 0.000 description 2
- NTAGWPPYNYPCLZ-UHFFFAOYSA-N 1-(4-methylphenyl)-4-[3-(5-phenylfuran-2-yl)propyl]piperazine Chemical compound C1=CC(C)=CC=C1N1CCN(CCCC=2OC(=CC=2)C=2C=CC=CC=2)CC1 NTAGWPPYNYPCLZ-UHFFFAOYSA-N 0.000 description 2
- PSXXTFAXJYBZIF-UHFFFAOYSA-N 1-(4-nitrophenyl)-4-[(5-phenylfuran-2-yl)methyl]piperazine Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1CCN(CC=2OC(=CC=2)C=2C=CC=CC=2)CC1 PSXXTFAXJYBZIF-UHFFFAOYSA-N 0.000 description 2
- JGCJCWBFGQNKSG-UHFFFAOYSA-N 1-[(5-methylfuran-2-yl)methyl]-4-phenylpiperazine Chemical compound O1C(C)=CC=C1CN1CCN(C=2C=CC=CC=2)CC1 JGCJCWBFGQNKSG-UHFFFAOYSA-N 0.000 description 2
- ODTHWSYRJVMUSA-UHFFFAOYSA-N 1-[(5-tert-butylfuran-2-yl)methyl]-4-phenylpiperazine Chemical compound O1C(C(C)(C)C)=CC=C1CN1CCN(C=2C=CC=CC=2)CC1 ODTHWSYRJVMUSA-UHFFFAOYSA-N 0.000 description 2
- CHSOHEAEPISALT-UHFFFAOYSA-N 1-[3-(5-phenylfuran-2-yl)propyl]-4-[3-(trifluoromethyl)phenyl]piperazine Chemical compound FC(F)(F)C1=CC=CC(N2CCN(CCCC=3OC(=CC=3)C=3C=CC=CC=3)CC2)=C1 CHSOHEAEPISALT-UHFFFAOYSA-N 0.000 description 2
- XCKAPWITOIAZFI-UHFFFAOYSA-N 1-[3-[5-(3,4-dichlorophenyl)furan-2-yl]propyl]-4-(4-methylphenyl)piperazine Chemical compound C1=CC(C)=CC=C1N1CCN(CCCC=2OC(=CC=2)C=2C=C(Cl)C(Cl)=CC=2)CC1 XCKAPWITOIAZFI-UHFFFAOYSA-N 0.000 description 2
- ZZWNNIQNXFJHGR-UHFFFAOYSA-N 1-[[5-(4-methoxyphenyl)furan-2-yl]methyl]-4-(4-methylphenyl)piperazine Chemical compound C1=CC(OC)=CC=C1C(O1)=CC=C1CN1CCN(C=2C=CC(C)=CC=2)CC1 ZZWNNIQNXFJHGR-UHFFFAOYSA-N 0.000 description 2
- JQZAAXONFICWOX-UHFFFAOYSA-N 1-[[5-(4-methoxyphenyl)furan-2-yl]methyl]-4-phenylpiperazine Chemical compound C1=CC(OC)=CC=C1C(O1)=CC=C1CN1CCN(C=2C=CC=CC=2)CC1 JQZAAXONFICWOX-UHFFFAOYSA-N 0.000 description 2
- UZDJZCPPAJVEQJ-UHFFFAOYSA-N 1-[[5-[4-chloro-3-(trifluoromethyl)phenyl]furan-2-yl]methyl]-4-(4-fluorophenyl)piperazine Chemical compound C1=CC(F)=CC=C1N1CCN(CC=2OC(=CC=2)C=2C=C(C(Cl)=CC=2)C(F)(F)F)CC1 UZDJZCPPAJVEQJ-UHFFFAOYSA-N 0.000 description 2
- YGTQGKPFUWLVQV-UHFFFAOYSA-N 1-phenyl-4-[3-(5-phenylfuran-2-yl)propyl]piperazine Chemical compound C=1C=C(C=2C=CC=CC=2)OC=1CCCN(CC1)CCN1C1=CC=CC=C1 YGTQGKPFUWLVQV-UHFFFAOYSA-N 0.000 description 2
- BYVARESVDFFVAV-UHFFFAOYSA-N 1-phenyl-4-[[5-[3-(trifluoromethyl)phenyl]furan-2-yl]methyl]piperazine Chemical compound FC(F)(F)C1=CC=CC(C=2OC(CN3CCN(CC3)C=3C=CC=CC=3)=CC=2)=C1 BYVARESVDFFVAV-UHFFFAOYSA-N 0.000 description 2
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- XQLRHFNLEFQVNU-UHFFFAOYSA-N n-[3-[4-[(4-benzylfuran-2-yl)methyl]piperazin-1-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(N2CCN(CC=3OC=C(CC=4C=CC=CC=4)C=3)CC2)=C1 XQLRHFNLEFQVNU-UHFFFAOYSA-N 0.000 description 1
- SNACRZQMOMMHLD-UHFFFAOYSA-N n-[3-[4-[(4-benzylthiophen-2-yl)methyl]piperazin-1-yl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(N2CCN(CC=3SC=C(CC=4C=CC=CC=4)C=3)CC2)=C1 SNACRZQMOMMHLD-UHFFFAOYSA-N 0.000 description 1
- RKHHXXQWDJFGPJ-UHFFFAOYSA-N n-[4-[4-[(4-phenyl-1,3-thiazol-2-yl)methyl]piperazin-1-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1N1CCN(CC=2SC=C(N=2)C=2C=CC=CC=2)CC1 RKHHXXQWDJFGPJ-UHFFFAOYSA-N 0.000 description 1
- DEGXEBQXKJOSTK-UHFFFAOYSA-N n-[4-[4-[(5-phenylthiophen-2-yl)methyl]piperazin-1-yl]phenyl]methanesulfonamide Chemical compound C1=CC(NS(=O)(=O)C)=CC=C1N1CCN(CC=2SC(=CC=2)C=2C=CC=CC=2)CC1 DEGXEBQXKJOSTK-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 229940055577 oleyl alcohol Drugs 0.000 description 1
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002916 oxazoles Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008024 pharmaceutical diluent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229940113116 polyethylene glycol 1000 Drugs 0.000 description 1
- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- SUVIGLJNEAMWEG-UHFFFAOYSA-N propane-1-thiol Chemical compound CCCS SUVIGLJNEAMWEG-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- XVSFHIIADLZQJP-UHFFFAOYSA-M sodium;propane-1-thiolate Chemical compound [Na+].CCC[S-] XVSFHIIADLZQJP-UHFFFAOYSA-M 0.000 description 1
- 229960005078 sorbitan sesquioleate Drugs 0.000 description 1
- 235000019337 sorbitan trioleate Nutrition 0.000 description 1
- 229960000391 sorbitan trioleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen 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
- C07D295/04—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
- C07D295/14—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—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 carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/42—Singly bound oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pulmonology (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB16526/76A GB1575904A (en) | 1976-04-23 | 1976-04-23 | Phenyl piperazines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU176820B true HU176820B (en) | 1981-05-28 |
Family
ID=10078930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU77LI311A HU176820B (en) | 1976-04-23 | 1977-04-22 | Process for preparing phenyl-piperazine derivatives |
Country Status (34)
| Country | Link |
|---|---|
| JP (1) | JPS52151183A (cs) |
| AR (2) | AR222003A1 (cs) |
| AT (1) | AT355579B (cs) |
| AU (1) | AU514822B2 (cs) |
| BE (1) | BE853899A (cs) |
| BG (2) | BG28055A3 (cs) |
| CA (1) | CA1087617A (cs) |
| CH (2) | CH633009A5 (cs) |
| CS (1) | CS196360B2 (cs) |
| DD (1) | DD129790A5 (cs) |
| DE (1) | DE2717415A1 (cs) |
| DK (1) | DK176177A (cs) |
| ES (2) | ES457988A1 (cs) |
| FI (1) | FI63937C (cs) |
| FR (1) | FR2348925A1 (cs) |
| GB (1) | GB1575904A (cs) |
| GR (1) | GR64084B (cs) |
| HU (1) | HU176820B (cs) |
| IE (1) | IE44730B1 (cs) |
| IL (1) | IL51787A (cs) |
| LU (1) | LU77170A1 (cs) |
| MX (1) | MX4596E (cs) |
| NL (1) | NL7704456A (cs) |
| NO (1) | NO146710C (cs) |
| NZ (1) | NZ183715A (cs) |
| OA (1) | OA05643A (cs) |
| PH (1) | PH14124A (cs) |
| PL (1) | PL117466B1 (cs) |
| PT (1) | PT66452B (cs) |
| RO (1) | RO72831A (cs) |
| SE (1) | SE7704536L (cs) |
| SU (2) | SU664564A3 (cs) |
| YU (1) | YU104477A (cs) |
| ZA (1) | ZA771849B (cs) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1601310A (en) * | 1978-05-23 | 1981-10-28 | Lilly Industries Ltd | Aryl hydantoins |
| DE3142608A1 (de) * | 1981-10-28 | 1983-05-05 | Basf Ag, 6700 Ludwigshafen | Polyazofarbstoffe |
| JPH07157477A (ja) * | 1993-12-02 | 1995-06-20 | Asahi Kagaku Kogyo Kk | チアゾール誘導体の製造方法 |
| KR970701705A (ko) * | 1994-03-11 | 1997-04-12 | 오노다 마사요시 | 5-HT₃ 수용체 효능제, 신규한 티아졸 유도체 및 이의 중간체(5-HT₃receptor agonist, novel thiazole derivative, and intermediate therefor) |
| CA2144669A1 (en) * | 1994-03-29 | 1995-09-30 | Kozo Akasaka | Biphenyl derivatives |
| GB9517381D0 (en) * | 1995-08-24 | 1995-10-25 | Pharmacia Spa | Aryl and heteroaryl piperazine derivatives |
| DZ3292A1 (fr) * | 2001-09-13 | 2005-05-14 | Solvay Pharm Gmbh | Nouveaux composes de type 1-[1-(hetero)aryl-1-perhydroxyalkylmethyl]piperazine, methodes pour les preparer et medicaments renfermant cescomposes |
| US8927546B2 (en) | 2006-02-28 | 2015-01-06 | Dart Neuroscience (Cayman) Ltd. | Therapeutic piperazines |
| CN101490017B (zh) | 2006-02-28 | 2013-01-23 | 海利空医疗公司 | 作为pde4抑制剂的用于治疗的哌嗪类 |
-
1976
- 1976-04-23 GB GB16526/76A patent/GB1575904A/en not_active Expired
-
1977
- 1977-03-28 NZ NZ183715A patent/NZ183715A/xx unknown
- 1977-03-28 ZA ZA00771849A patent/ZA771849B/xx unknown
- 1977-03-30 IL IL51787A patent/IL51787A/xx unknown
- 1977-03-30 CA CA275,160A patent/CA1087617A/en not_active Expired
- 1977-03-30 IE IE671/77A patent/IE44730B1/en unknown
- 1977-04-13 CH CH525781A patent/CH633009A5/fr not_active IP Right Cessation
- 1977-04-13 CH CH455777A patent/CH625802A5/fr not_active IP Right Cessation
- 1977-04-13 MX MX775629U patent/MX4596E/es unknown
- 1977-04-14 PH PH19656A patent/PH14124A/en unknown
- 1977-04-18 AU AU24386/77A patent/AU514822B2/en not_active Expired
- 1977-04-18 PT PT66452A patent/PT66452B/pt unknown
- 1977-04-19 FR FR7711669A patent/FR2348925A1/fr active Granted
- 1977-04-19 GR GR53236A patent/GR64084B/el unknown
- 1977-04-20 OA OA56149A patent/OA05643A/xx unknown
- 1977-04-20 SE SE7704536A patent/SE7704536L/xx not_active Application Discontinuation
- 1977-04-20 ES ES457988A patent/ES457988A1/es not_active Expired
- 1977-04-20 DE DE19772717415 patent/DE2717415A1/de not_active Withdrawn
- 1977-04-20 BG BG037191A patent/BG28055A3/xx unknown
- 1977-04-20 RO RO7790106A patent/RO72831A/ro unknown
- 1977-04-20 BG BG036062A patent/BG27746A3/xx unknown
- 1977-04-21 LU LU77170A patent/LU77170A1/xx unknown
- 1977-04-21 CS CS772668A patent/CS196360B2/cs unknown
- 1977-04-21 YU YU01044/77A patent/YU104477A/xx unknown
- 1977-04-21 DK DK176177A patent/DK176177A/da not_active Application Discontinuation
- 1977-04-22 DD DD7700198558A patent/DD129790A5/xx unknown
- 1977-04-22 PL PL1977197550A patent/PL117466B1/pl unknown
- 1977-04-22 AT AT285177A patent/AT355579B/de not_active IP Right Cessation
- 1977-04-22 NL NL7704456A patent/NL7704456A/xx not_active Application Discontinuation
- 1977-04-22 BE BE6045977A patent/BE853899A/xx not_active IP Right Cessation
- 1977-04-22 FI FI771287A patent/FI63937C/fi not_active IP Right Cessation
- 1977-04-22 AR AR267310A patent/AR222003A1/es active
- 1977-04-22 SU SU772474105A patent/SU664564A3/ru active
- 1977-04-22 NO NO771398A patent/NO146710C/no unknown
- 1977-04-22 HU HU77LI311A patent/HU176820B/hu unknown
- 1977-04-23 JP JP4727677A patent/JPS52151183A/ja active Pending
- 1977-12-28 SU SU772558499A patent/SU727146A3/ru active
-
1978
- 1978-03-16 ES ES467948A patent/ES467948A1/es not_active Expired
- 1978-03-22 AR AR271519A patent/AR222635A1/es active
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