GB1575904A - Phenyl piperazines - Google Patents
Phenyl piperazines Download PDFInfo
- Publication number
- GB1575904A GB1575904A GB16526/76A GB1652676A GB1575904A GB 1575904 A GB1575904 A GB 1575904A GB 16526/76 A GB16526/76 A GB 16526/76A GB 1652676 A GB1652676 A GB 1652676A GB 1575904 A GB1575904 A GB 1575904A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- piperazine
- phenylpiperazine
- ylmethyl
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical class C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 75
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 42
- 150000003839 salts Chemical class 0.000 claims abstract description 28
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 13
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 8
- 229930192474 thiophene Chemical group 0.000 claims abstract description 7
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 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
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 13
- 150000002367 halogens Chemical class 0.000 claims description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 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 claims description 3
- 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 claims 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 claims description 3
- 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 claims description 3
- 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 3
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 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 claims 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 claims description 2
- 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 claims 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 claims description 2
- BXYDDVIECGIBTF-UHFFFAOYSA-N 1-phenyl-4-[4-(5-phenylthiophen-2-yl)butan-2-yl]piperazine Chemical compound C1(=CC=CC=C1)C1=CC=C(S1)CCC(C)N1CCN(CC1)C1=CC=CC=C1 BXYDDVIECGIBTF-UHFFFAOYSA-N 0.000 claims description 2
- 125000004803 chlorobenzyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- ABCSPNANFXDHDU-UHFFFAOYSA-N 2-benzyl-1,3-thiazole Chemical compound C=1C=CC=CC=1CC1=NC=CS1 ABCSPNANFXDHDU-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 5
- 230000001225 therapeutic effect Effects 0.000 abstract description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 2
- 241000124008 Mammalia Species 0.000 abstract description 2
- 208000006673 asthma Diseases 0.000 abstract description 2
- 238000009833 condensation Methods 0.000 abstract description 2
- 230000005494 condensation Effects 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- 239000000203 mixture Substances 0.000 description 36
- -1 PHENYL PIPERAZINES Chemical class 0.000 description 35
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 34
- 239000003921 oil Substances 0.000 description 33
- 239000000243 solution Substances 0.000 description 33
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
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- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 17
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
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- 239000002904 solvent Substances 0.000 description 12
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 8
- 235000019341 magnesium sulphate Nutrition 0.000 description 8
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- 230000003226 decolorizating effect Effects 0.000 description 6
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
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- 235000017550 sodium carbonate Nutrition 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
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- JJDXREXQSCIIJY-UHFFFAOYSA-N (2-amino-2-sulfanylideneethyl) acetate Chemical compound CC(=O)OCC(N)=S JJDXREXQSCIIJY-UHFFFAOYSA-N 0.000 description 3
- 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 3
- VKGLKWKQBWOENE-UHFFFAOYSA-N 2-(4-chlorophenyl)furan Chemical compound C1=CC(Cl)=CC=C1C1=CC=CO1 VKGLKWKQBWOENE-UHFFFAOYSA-N 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
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- 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
- LQLTYMKINLYYGJ-UHFFFAOYSA-N n-[4-[4-[(5-phenyl-1,3-oxazol-2-yl)methyl]piperazin-1-yl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1N1CCN(CC=2OC(=CN=2)C=2C=CC=CC=2)CC1 LQLTYMKINLYYGJ-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
- DXRQITWEIMAHEN-UHFFFAOYSA-N n-phenacyl-3-(4-phenylpiperazin-1-yl)propanamide Chemical compound C=1C=CC=CC=1C(=O)CNC(=O)CCN(CC1)CCN1C1=CC=CC=C1 DXRQITWEIMAHEN-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 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
- 239000012044 organic layer Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002916 oxazoles Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-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
- 150000004885 piperazines Chemical class 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
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920006316 polyvinylpyrrolidine Polymers 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000012056 semi-solid material Substances 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
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 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
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
- XVSFHIIADLZQJP-UHFFFAOYSA-M sodium;propane-1-thiolate Chemical compound [Na+].CCC[S-] XVSFHIIADLZQJP-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 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
- 239000008117 stearic acid Substances 0.000 description 1
- 239000012058 sterile packaged powder Substances 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000001117 sulphuric acid 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
- 239000007916 tablet composition Substances 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003511 tertiary amides Chemical class 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 229940100611 topical cream Drugs 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 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
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 239000003981 vehicle Substances 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Priority Applications (40)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB16526/76A GB1575904A (en) | 1976-04-23 | 1976-04-23 | Phenyl piperazines |
| ZA00771849A ZA771849B (en) | 1976-04-23 | 1977-03-28 | Phenyl piperazines |
| NZ183715A NZ183715A (en) | 1976-04-23 | 1977-03-28 | Phenylpiperazine derivatives |
| CA275,160A CA1087617A (en) | 1976-04-23 | 1977-03-30 | Phenyl piperazines |
| IE671/77A IE44730B1 (en) | 1976-04-23 | 1977-03-30 | Phenyl piperazines |
| IL51787A IL51787A (en) | 1976-04-23 | 1977-03-30 | 1 heterocyclylalkyl 4 phenyl piperazine derivatives their preparation and pharmaceutical compositions containing them |
| CH455777A CH625802A5 (en) | 1976-04-23 | 1977-04-13 | Process for the preparation of phenylpiperazine derivatives |
| CH525781A CH633009A5 (en) | 1976-04-23 | 1977-04-13 | Process for the preparation of new phenylpiperazine derivatives |
| MX775629U MX4596E (es) | 1976-04-23 | 1977-04-13 | Procedimiento para preparar un derivado de fenilpiperazina |
| PH19656A PH14124A (en) | 1976-04-23 | 1977-04-14 | Phenyl piperazines |
| PT66452A PT66452B (en) | 1976-04-23 | 1977-04-18 | Process for preparing a phenylpiperazine |
| AU24386/77A AU514822B2 (en) | 1976-04-23 | 1977-04-18 | Phenyl diperazines derivatives |
| FR7711669A FR2348925A1 (fr) | 1976-04-23 | 1977-04-19 | Derives de phenylpiperazine |
| GR53236A GR64084B (en) | 1976-04-23 | 1977-04-19 | Method for the preparation of phenyl piperazines |
| DE19772717415 DE2717415A1 (de) | 1976-04-23 | 1977-04-20 | Verfahren zur herstellung von phenylpiperazinderivaten, phenylpiperazinderivate und diese enthaltende pharmazeutische zubereitungen |
| OA56149A OA05643A (fr) | 1976-04-23 | 1977-04-20 | Dérivés de phénylpipérazine. |
| ES457988A ES457988A1 (es) | 1976-04-23 | 1977-04-20 | Un procedimiento de preparacion de un derivado de fenilpipe-razina. |
| RO7790106A RO72831A (ro) | 1976-04-23 | 1977-04-20 | Procedeu pentru prepararea unor fenilpiperazine |
| SE7704536A SE7704536L (sv) | 1976-04-23 | 1977-04-20 | Forfarande for framstellning av fenylpiperazinderivat |
| BG036062A BG27746A3 (bg) | 1976-04-23 | 1977-04-20 | Метод за получаване на фенилпиперазинови производни |
| BG037191A BG28055A3 (bg) | 1976-04-23 | 1977-04-20 | Метод за получаване на фенилпиперазинови производни |
| YU01044/77A YU104477A (en) | 1976-04-23 | 1977-04-21 | Process for obtaining phenyl piperazine derivatives |
| DK176177A DK176177A (da) | 1976-04-23 | 1977-04-21 | Fremgangsmade til fremstilling af phenylpiperaziner |
| LU77170A LU77170A1 (enExample) | 1976-04-23 | 1977-04-21 | |
| CS772668A CS196360B2 (en) | 1976-04-23 | 1977-04-21 | Process for preparing derivatives of phenylpiperazine |
| AR267310A AR222003A1 (es) | 1976-04-23 | 1977-04-22 | Procedimiento para la preparacion de derivados de fenilpiperazina |
| FI771287A FI63937C (fi) | 1976-04-23 | 1977-04-22 | Foerfarande foer framstaellning av terapeutiskt anvaendbara feylpiperaziner |
| BE6045977A BE853899A (fr) | 1976-04-23 | 1977-04-22 | Derives de phenylpiperazine |
| AT285177A AT355579B (de) | 1976-04-23 | 1977-04-22 | Verfahren zur herstellung von neuen phenyl- piperazinderivaten und deren salzen |
| NL7704456A NL7704456A (nl) | 1976-04-23 | 1977-04-22 | Werkwijze voor de bereiding van farmaceutisch werkzame fenylpiperazinen, werkwijze voor de bereiding van een farmaceutisch preparaat en preparaat, verkregen volgens deze werkwijze. |
| NO771398A NO146710C (no) | 1976-04-23 | 1977-04-22 | Analogifremgangsmaate for fremstilling av terapeutisk aktive fenylpiperazinderivater |
| DD7700198558A DD129790A5 (de) | 1976-04-23 | 1977-04-22 | Verfahren zur herstellung von phenylpiperazinderivaten |
| SU772474105A SU664564A3 (ru) | 1976-04-23 | 1977-04-22 | Способ получени производных фенилпиперазина или их солей |
| PL1977197550A PL117466B1 (en) | 1976-04-23 | 1977-04-22 | Process for preparing novel derivatives of phenylopiperazine |
| HU77LI311A HU176820B (en) | 1976-04-23 | 1977-04-22 | Process for preparing phenyl-piperazine derivatives |
| JP4727677A JPS52151183A (en) | 1976-04-23 | 1977-04-23 | Phenylpyperazine |
| US05/813,912 US4123529A (en) | 1976-04-23 | 1977-07-08 | Phenylpiperazine derivatives |
| SU772558499A SU727146A3 (ru) | 1976-04-23 | 1977-12-28 | Способ получени производных фенилпиперазина или их солей |
| ES467948A ES467948A1 (es) | 1976-04-23 | 1978-03-16 | Un procedimiento para la preparacion de un derivado de fe- nilpiperazina. |
| AR271519A AR222635A1 (es) | 1976-04-23 | 1978-03-22 | Procedimiento para la preparacion de derivados de fenilpiperazina |
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 |
|---|---|
| GB1575904A true GB1575904A (en) | 1980-10-01 |
Family
ID=10078930
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB16526/76A Expired GB1575904A (en) | 1976-04-23 | 1976-04-23 | Phenyl piperazines |
Country Status (34)
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007100852A1 (en) * | 2006-02-28 | 2007-09-07 | Helicon Therapeutics, Inc. | Therapeutic piperazines as pde4 inhibitors |
| US8927546B2 (en) | 2006-02-28 | 2015-01-06 | Dart Neuroscience (Cayman) Ltd. | Therapeutic piperazines |
Families Citing this family (7)
| 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 |
-
1976
- 1976-04-23 GB GB16526/76A patent/GB1575904A/en not_active Expired
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1977
- 1977-03-28 ZA ZA00771849A patent/ZA771849B/xx unknown
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- 1977-03-30 CA CA275,160A patent/CA1087617A/en not_active Expired
- 1977-03-30 IL IL51787A patent/IL51787A/xx unknown
- 1977-04-13 CH CH525781A patent/CH633009A5/fr not_active IP Right Cessation
- 1977-04-13 MX MX775629U patent/MX4596E/es unknown
- 1977-04-13 CH CH455777A patent/CH625802A5/fr not_active IP Right Cessation
- 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 RO RO7790106A patent/RO72831A/ro unknown
- 1977-04-20 DE DE19772717415 patent/DE2717415A1/de not_active Withdrawn
- 1977-04-20 BG BG036062A patent/BG27746A3/xx unknown
- 1977-04-20 BG BG037191A patent/BG28055A3/xx unknown
- 1977-04-20 OA OA56149A patent/OA05643A/xx unknown
- 1977-04-20 ES ES457988A patent/ES457988A1/es not_active Expired
- 1977-04-20 SE SE7704536A patent/SE7704536L/xx not_active Application Discontinuation
- 1977-04-21 DK DK176177A patent/DK176177A/da not_active Application Discontinuation
- 1977-04-21 CS CS772668A patent/CS196360B2/cs unknown
- 1977-04-21 LU LU77170A patent/LU77170A1/xx unknown
- 1977-04-21 YU YU01044/77A patent/YU104477A/xx unknown
- 1977-04-22 FI FI771287A patent/FI63937C/fi not_active IP Right Cessation
- 1977-04-22 AT AT285177A patent/AT355579B/de not_active IP Right Cessation
- 1977-04-22 BE BE6045977A patent/BE853899A/xx not_active IP Right Cessation
- 1977-04-22 HU HU77LI311A patent/HU176820B/hu unknown
- 1977-04-22 NO NO771398A patent/NO146710C/no unknown
- 1977-04-22 NL NL7704456A patent/NL7704456A/xx not_active Application Discontinuation
- 1977-04-22 DD DD7700198558A patent/DD129790A5/xx unknown
- 1977-04-22 AR AR267310A patent/AR222003A1/es active
- 1977-04-22 PL PL1977197550A patent/PL117466B1/pl unknown
- 1977-04-22 SU SU772474105A patent/SU664564A3/ru active
- 1977-04-23 JP JP4727677A patent/JPS52151183A/ja active Pending
- 1977-12-28 SU SU772558499A patent/SU727146A3/ru active
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1978
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007100852A1 (en) * | 2006-02-28 | 2007-09-07 | Helicon Therapeutics, Inc. | Therapeutic piperazines as pde4 inhibitors |
| US7829713B2 (en) | 2006-02-28 | 2010-11-09 | Helicon Therapeutics, Inc. | Therapeutic piperazines |
| US8338405B2 (en) | 2006-02-28 | 2012-12-25 | Dart Neuroscience Llc | Therapeutic piperazines |
| AU2007221021B2 (en) * | 2006-02-28 | 2013-01-17 | Dart Neuroscience (Cayman) Ltd | Therapeutic piperazines as PDE4 inhibitors |
| US8501745B2 (en) | 2006-02-28 | 2013-08-06 | Dart Neuroscience (Cayman) Ltd. | Piperazine PDE4 inhibitors and uses thereof |
| US8927546B2 (en) | 2006-02-28 | 2015-01-06 | Dart Neuroscience (Cayman) Ltd. | Therapeutic piperazines |
| US9624200B2 (en) | 2006-02-28 | 2017-04-18 | Dart Neuroscience (Cayman) Ltd. | Therapeutic piperazines |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |