CH633009A5 - Process for the preparation of new phenylpiperazine derivatives - Google Patents
Process for the preparation of new phenylpiperazine derivatives Download PDFInfo
- Publication number
- CH633009A5 CH633009A5 CH525781A CH696480A CH633009A5 CH 633009 A5 CH633009 A5 CH 633009A5 CH 525781 A CH525781 A CH 525781A CH 696480 A CH696480 A CH 696480A CH 633009 A5 CH633009 A5 CH 633009A5
- Authority
- CH
- Switzerland
- Prior art keywords
- phenyl
- optionally substituted
- piperazine
- formula
- alkyl
- Prior art date
Links
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000000034 method Methods 0.000 title claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 35
- -1 5-thiazolyl group Chemical group 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 23
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 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
- 229930192474 thiophene Chemical group 0.000 claims abstract description 6
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 2
- 101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 claims 1
- 101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 claims 1
- 208000001718 Immediate Hypersensitivity Diseases 0.000 abstract description 2
- 206010045240 Type I hypersensitivity Diseases 0.000 abstract description 2
- 208000006673 asthma Diseases 0.000 abstract description 2
- 208000010216 atopic IgE responsiveness 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
- 230000000069 prophylactic effect Effects 0.000 abstract description 2
- 230000001225 therapeutic effect Effects 0.000 abstract description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 241000124008 Mammalia Species 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
- 239000002253 acid Substances 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000007513 acids Chemical class 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- 238000004806 packaging method and process Methods 0.000 description 4
- 229960005141 piperazine Drugs 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 101100521345 Mus musculus Prop1 gene Proteins 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 108700017836 Prophet of Pit-1 Proteins 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 2
- 150000003557 thiazoles Chemical class 0.000 description 2
- CUNWUEBNSZSNRX-RKGWDQTMSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;(z)-octadec-9-enoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O CUNWUEBNSZSNRX-RKGWDQTMSA-N 0.000 description 1
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- UWYVPFMHMJIBHE-OWOJBTEDSA-N (e)-2-hydroxybut-2-enedioic acid Chemical compound OC(=O)\C=C(\O)C(O)=O UWYVPFMHMJIBHE-OWOJBTEDSA-N 0.000 description 1
- RMVWZPKAJXGDLZ-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-[3-(5-methylfuran-2-yl)propyl]piperazine Chemical compound O1C(C)=CC=C1CCCN1CCN(C=2C(=CC=CC=2)Cl)CC1 RMVWZPKAJXGDLZ-UHFFFAOYSA-N 0.000 description 1
- HEASYVDSWBSHHR-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-[3-(5-methylthiophen-2-yl)propyl]piperazine Chemical compound S1C(C)=CC=C1CCCN1CCN(C=2C(=CC=CC=2)Cl)CC1 HEASYVDSWBSHHR-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZNDDSYAHAFLAQG-UHFFFAOYSA-N 1-(3-chlorophenyl)-4-[(5-methylfuran-2-yl)methyl]piperazine Chemical compound O1C(C)=CC=C1CN1CCN(C=2C=C(Cl)C=CC=2)CC1 ZNDDSYAHAFLAQG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZJSKLQMRROAOFR-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-[2-(5-methylfuran-2-yl)ethyl]piperazine Chemical compound O1C(C)=CC=C1CCN1CCN(C=2C=CC(Cl)=CC=2)CC1 ZJSKLQMRROAOFR-UHFFFAOYSA-N 0.000 description 1
- SNVDLLXQHFFRGT-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-[2-(5-methylthiophen-2-yl)ethyl]piperazine Chemical compound S1C(C)=CC=C1CCN1CCN(C=2C=CC(Cl)=CC=2)CC1 SNVDLLXQHFFRGT-UHFFFAOYSA-N 0.000 description 1
- CVQHFSRFVLVULV-UHFFFAOYSA-N 1-(4-chlorophenyl)-4-[2-(5-phenylfuran-2-yl)ethyl]piperazine Chemical compound C1=CC(Cl)=CC=C1N1CCN(CCC=2OC(=CC=2)C=2C=CC=CC=2)CC1 CVQHFSRFVLVULV-UHFFFAOYSA-N 0.000 description 1
- DPEWTQJUUDLJNX-UHFFFAOYSA-N 1-(4-ethoxyphenyl)piperazine Chemical compound C1=CC(OCC)=CC=C1N1CCNCC1 DPEWTQJUUDLJNX-UHFFFAOYSA-N 0.000 description 1
- RLABBVYISMVSTG-UHFFFAOYSA-N 1-(4-methoxyphenyl)-4-[(5-phenylthiophen-2-yl)methyl]piperazine Chemical compound C1=CC(OC)=CC=C1N1CCN(CC=2SC(=CC=2)C=2C=CC=CC=2)CC1 RLABBVYISMVSTG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- ONEYFZXGNFNRJH-UHFFFAOYSA-N 1-(4-methylphenyl)piperazine Chemical compound C1=CC(C)=CC=C1N1CCNCC1 ONEYFZXGNFNRJH-UHFFFAOYSA-N 0.000 description 1
- VWOJSRICSKDKAW-UHFFFAOYSA-N 1-(4-nitrophenyl)piperazine Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1CCNCC1 VWOJSRICSKDKAW-UHFFFAOYSA-N 0.000 description 1
- FWEBUUYZJJXOOM-UHFFFAOYSA-N 1-[(5-benzylfuran-2-yl)methyl]-4-(4-nitrophenyl)piperazine Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1CCN(CC=2OC(CC=3C=CC=CC=3)=CC=2)CC1 FWEBUUYZJJXOOM-UHFFFAOYSA-N 0.000 description 1
- SHWBLTAQTWPNDM-UHFFFAOYSA-N 1-[(5-benzylthiophen-2-yl)methyl]-4-(4-nitrophenyl)piperazine Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1CCN(CC=2SC(CC=3C=CC=CC=3)=CC=2)CC1 SHWBLTAQTWPNDM-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AEPZJPIAGFJEGT-UHFFFAOYSA-N 1-[(5-methylthiophen-2-yl)methyl]-4-phenylpiperazine Chemical compound S1C(C)=CC=C1CN1CCN(C=2C=CC=CC=2)CC1 AEPZJPIAGFJEGT-UHFFFAOYSA-N 0.000 description 1
- YICOOFFFJYDRAG-UHFFFAOYSA-N 1-[2-(4-methylfuran-2-yl)ethyl]-4-(3-methylphenyl)piperazine Chemical compound CC1=COC(CCN2CCN(CC2)C=2C=C(C)C=CC=2)=C1 YICOOFFFJYDRAG-UHFFFAOYSA-N 0.000 description 1
- YCAOCUFHMHTCDG-UHFFFAOYSA-N 1-[2-(5-benzylfuran-2-yl)ethyl]-4-(4-ethylphenyl)piperazine Chemical compound C1=CC(CC)=CC=C1N1CCN(CCC=2OC(CC=3C=CC=CC=3)=CC=2)CC1 YCAOCUFHMHTCDG-UHFFFAOYSA-N 0.000 description 1
- YVWWGVKRDSVNER-UHFFFAOYSA-N 1-[2-(5-benzylthiophen-2-yl)ethyl]-4-(4-ethylphenyl)piperazine Chemical compound C1=CC(CC)=CC=C1N1CCN(CCC=2SC(CC=3C=CC=CC=3)=CC=2)CC1 YVWWGVKRDSVNER-UHFFFAOYSA-N 0.000 description 1
- NYKKNMHZSUQSTB-UHFFFAOYSA-N 1-[3-(5-benzylfuran-2-yl)propyl]-4-(4-ethoxyphenyl)piperazine Chemical compound C1=CC(OCC)=CC=C1N1CCN(CCCC=2OC(CC=3C=CC=CC=3)=CC=2)CC1 NYKKNMHZSUQSTB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- BQYFJDYYJZLQJV-UHFFFAOYSA-N 1-[[5-(3,4-dichlorophenyl)furan-2-yl]methyl]-4-[3-(trifluoromethyl)phenyl]piperazine;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC=CC(N2CCN(CC=3OC(=CC=3)C=3C=C(Cl)C(Cl)=CC=3)CC2)=C1 BQYFJDYYJZLQJV-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ISRUOZWLYKHEJK-UHFFFAOYSA-N 1-phenyl-4-[2-(5-phenylthiophen-2-yl)butyl]piperazine Chemical compound C=1C=C(C=2C=CC=CC=2)SC=1C(CC)CN(CC1)CCN1C1=CC=CC=C1 ISRUOZWLYKHEJK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- IYEYEHOIEHGEKJ-UHFFFAOYSA-N 2-[1-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-4-phenyl-1,3-thiazole Chemical compound N=1C(C=2C=CC=CC=2)=CSC=1C(C)N(CC1)CCN1C1=CC=C(C)C=C1 IYEYEHOIEHGEKJ-UHFFFAOYSA-N 0.000 description 1
- GACCNQRSVVGFIT-UHFFFAOYSA-N 2-[1-[4-(4-methylphenyl)piperazin-1-yl]ethyl]-5-phenyl-1,3-oxazole Chemical compound N=1C=C(C=2C=CC=CC=2)OC=1C(C)N(CC1)CCN1C1=CC=C(C)C=C1 GACCNQRSVVGFIT-UHFFFAOYSA-N 0.000 description 1
- JZWWJQNBPJPQGA-UHFFFAOYSA-N 2-[2-[4-(4-chlorophenyl)piperazin-1-yl]ethyl]-5-methyl-1,3-oxazole Chemical compound O1C(C)=CN=C1CCN1CCN(C=2C=CC(Cl)=CC=2)CC1 JZWWJQNBPJPQGA-UHFFFAOYSA-N 0.000 description 1
- RDWBQVZTEJJUFL-UHFFFAOYSA-N 2-[2-[4-(4-chlorophenyl)piperazin-1-yl]ethyl]-5-phenyl-1,3-oxazole Chemical compound C1=CC(Cl)=CC=C1N1CCN(CCC=2OC(=CN=2)C=2C=CC=CC=2)CC1 RDWBQVZTEJJUFL-UHFFFAOYSA-N 0.000 description 1
- MJELUHMJJPAFHM-UHFFFAOYSA-N 2-[2-[4-(4-methylphenyl)piperazin-1-yl]propyl]-4-phenyl-1,3-thiazole Chemical compound C1CN(C=2C=CC(C)=CC=2)CCN1C(C)CC(SC=1)=NC=1C1=CC=CC=C1 MJELUHMJJPAFHM-UHFFFAOYSA-N 0.000 description 1
- HVGIFIZRMBDRMH-UHFFFAOYSA-N 2-[2-[4-(4-methylphenyl)piperazin-1-yl]propyl]-5-phenyl-1,3-oxazole Chemical compound C1CN(C=2C=CC(C)=CC=2)CCN1C(C)CC(O1)=NC=C1C1=CC=CC=C1 HVGIFIZRMBDRMH-UHFFFAOYSA-N 0.000 description 1
- DJVJNWWFPJWVIU-UHFFFAOYSA-N 2-[2-[4-(4-nitrophenyl)piperazin-1-yl]ethyl]-4-phenyl-1,3-thiazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1CCN(CCC=2SC=C(N=2)C=2C=CC=CC=2)CC1 DJVJNWWFPJWVIU-UHFFFAOYSA-N 0.000 description 1
- HRMACTPKDGDMBS-UHFFFAOYSA-N 2-[3-[4-(2-chlorophenyl)piperazin-1-yl]propyl]-5-methyl-1,3-oxazole Chemical compound CC1=CN=C(O1)CCCN1CCN(CC1)C1=C(C=CC=C1)Cl HRMACTPKDGDMBS-UHFFFAOYSA-N 0.000 description 1
- PSZGVEBPTIDAMJ-UHFFFAOYSA-N 2-[3-[4-(2-chlorophenyl)piperazin-1-yl]propyl]-5-methyl-1,3-thiazole Chemical compound S1C(C)=CN=C1CCCN1CCN(C=2C(=CC=CC=2)Cl)CC1 PSZGVEBPTIDAMJ-UHFFFAOYSA-N 0.000 description 1
- HMNKFNHXELLGTE-UHFFFAOYSA-N 2-[[2,3-dimethyl-4-(4-methylphenyl)piperazin-1-yl]methyl]-5-phenyl-1,3-oxazole Chemical compound CC1C(C)N(C=2C=CC(C)=CC=2)CCN1CC(O1)=NC=C1C1=CC=CC=C1 HMNKFNHXELLGTE-UHFFFAOYSA-N 0.000 description 1
- WDGRSAFRBFFKRK-UHFFFAOYSA-N 2-[[3-methyl-4-(4-methylphenyl)piperazin-1-yl]methyl]-5-phenyl-1,3-oxazole Chemical compound C1CN(C=2C=CC(C)=CC=2)C(C)CN1CC(O1)=NC=C1C1=CC=CC=C1 WDGRSAFRBFFKRK-UHFFFAOYSA-N 0.000 description 1
- JUSDHZJXSNQIQW-UHFFFAOYSA-N 2-[[4-(4-methylphenyl)piperazin-1-yl]methyl]-5-phenyl-1,3-oxazole Chemical compound C1=CC(C)=CC=C1N1CCN(CC=2OC(=CN=2)C=2C=CC=CC=2)CC1 JUSDHZJXSNQIQW-UHFFFAOYSA-N 0.000 description 1
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- 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 |
|---|---|
| CH633009A5 true CH633009A5 (en) | 1982-11-15 |
Family
ID=10078930
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH525781A CH633009A5 (en) | 1976-04-23 | 1977-04-13 | Process for the preparation of new phenylpiperazine derivatives |
| CH455777A CH625802A5 (en) | 1976-04-23 | 1977-04-13 | Process for the preparation of phenylpiperazine derivatives |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH455777A CH625802A5 (en) | 1976-04-23 | 1977-04-13 | Process for the preparation of phenylpiperazine 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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Legal Events
| Date | Code | Title | Description |
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| PL | Patent ceased | ||
| PL | Patent ceased |