MX2007007688A - Compuestos de fenilpiperazina nitro-sustituidos, su preparacion y uso en medicamentos. - Google Patents
Compuestos de fenilpiperazina nitro-sustituidos, su preparacion y uso en medicamentos.Info
- Publication number
- MX2007007688A MX2007007688A MX2007007688A MX2007007688A MX2007007688A MX 2007007688 A MX2007007688 A MX 2007007688A MX 2007007688 A MX2007007688 A MX 2007007688A MX 2007007688 A MX2007007688 A MX 2007007688A MX 2007007688 A MX2007007688 A MX 2007007688A
- Authority
- MX
- Mexico
- Prior art keywords
- alkyl
- group
- phenyl
- butyl
- radical
- Prior art date
Links
- -1 Nitro-substituted phenyl-piperazine compounds Chemical class 0.000 title claims abstract description 675
- 239000003814 drug Substances 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 21
- 238000011282 treatment Methods 0.000 claims abstract description 18
- 238000011321 prophylaxis Methods 0.000 claims abstract description 16
- 208000035475 disorder Diseases 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 13
- 230000008569 process Effects 0.000 claims abstract description 8
- 201000010099 disease Diseases 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 627
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 550
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 472
- 125000001424 substituent group Chemical group 0.000 claims description 261
- 229910052731 fluorine Inorganic materials 0.000 claims description 239
- 229910052794 bromium Inorganic materials 0.000 claims description 236
- 229910052801 chlorine Inorganic materials 0.000 claims description 220
- 229910052740 iodine Inorganic materials 0.000 claims description 217
- 239000000460 chlorine Substances 0.000 claims description 209
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 207
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 153
- 125000001544 thienyl group Chemical group 0.000 claims description 153
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 150
- 125000003118 aryl group Chemical group 0.000 claims description 142
- 125000002541 furyl group Chemical group 0.000 claims description 142
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 134
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 133
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 127
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 124
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 123
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 102
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 100
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 99
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 98
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 94
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 87
- 125000000335 thiazolyl group Chemical group 0.000 claims description 86
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 84
- 125000004076 pyridyl group Chemical group 0.000 claims description 80
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 80
- 150000001875 compounds Chemical class 0.000 claims description 75
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 74
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 74
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 74
- 125000002971 oxazolyl group Chemical group 0.000 claims description 74
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 74
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 74
- 125000001425 triazolyl group Chemical group 0.000 claims description 74
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 71
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims description 67
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 67
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 67
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 67
- 125000002883 imidazolyl group Chemical group 0.000 claims description 66
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 66
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 65
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 63
- 239000000203 mixture Substances 0.000 claims description 62
- 125000005842 heteroatom Chemical group 0.000 claims description 59
- 125000001624 naphthyl group Chemical group 0.000 claims description 59
- 229910052799 carbon Inorganic materials 0.000 claims description 48
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims description 44
- 229920006395 saturated elastomer Polymers 0.000 claims description 43
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 42
- 229910052717 sulfur Inorganic materials 0.000 claims description 42
- 239000011593 sulfur Substances 0.000 claims description 42
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 38
- 229910052760 oxygen Inorganic materials 0.000 claims description 38
- 239000001301 oxygen Substances 0.000 claims description 38
- 239000012453 solvate Substances 0.000 claims description 35
- 150000003254 radicals Chemical class 0.000 claims description 31
- 125000002947 alkylene group Chemical group 0.000 claims description 29
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 29
- 150000005840 aryl radicals Chemical class 0.000 claims description 24
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 21
- 125000001072 heteroaryl group Chemical group 0.000 claims description 18
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims description 17
- 239000012752 auxiliary agent Substances 0.000 claims description 16
- 239000012429 reaction media Substances 0.000 claims description 16
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims description 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 13
- 239000003054 catalyst Substances 0.000 claims description 13
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 12
- UVNXNSUKKOLFBM-UHFFFAOYSA-N imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=CSC2=NC=CN21 UVNXNSUKKOLFBM-UHFFFAOYSA-N 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 11
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical group OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
- HNCIKWSCVIYUBH-UHFFFAOYSA-N 5-(4-methylpiperazin-1-yl)-2-nitro-n-(2-pyrrol-1-ylethyl)aniline Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(NCCN2C=CC=C2)=C1 HNCIKWSCVIYUBH-UHFFFAOYSA-N 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 6
- 208000008589 Obesity Diseases 0.000 claims description 6
- 125000003725 azepanyl group Chemical group 0.000 claims description 6
- 125000002393 azetidinyl group Chemical group 0.000 claims description 6
- 125000004069 aziridinyl group Chemical group 0.000 claims description 6
- 230000001149 cognitive effect Effects 0.000 claims description 6
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 claims description 6
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000002757 morpholinyl group Chemical group 0.000 claims description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 6
- 235000020824 obesity Nutrition 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000003507 tetrahydrothiofenyl group Chemical group 0.000 claims description 6
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 6
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 5
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 235000013305 food Nutrition 0.000 claims description 5
- 230000037406 food intake Effects 0.000 claims description 5
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- MYBGUIWPZVAIMK-UHFFFAOYSA-N 2-[5-(4-methylpiperazin-1-yl)-2-nitrophenyl]pyridazin-3-one Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(N2C(C=CC=N2)=O)=C1 MYBGUIWPZVAIMK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004419 alkynylene group Chemical group 0.000 claims description 4
- FSMCLELVLWKGBI-UHFFFAOYSA-N n-[5-(4-methylpiperazin-1-yl)-2-nitrophenyl]benzamide Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(NC(=O)C=2C=CC=CC=2)=C1 FSMCLELVLWKGBI-UHFFFAOYSA-N 0.000 claims description 4
- PNWSCBBGAAPCOT-UHFFFAOYSA-N n-[5-(4-methylpiperazin-1-yl)-2-nitrophenyl]pyrrol-1-amine Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(NN2C=CC=C2)=C1 PNWSCBBGAAPCOT-UHFFFAOYSA-N 0.000 claims description 4
- WHNPCQMONQGNSL-UHFFFAOYSA-N n-benzyl-5-(4-butylpiperazin-1-yl)-2-nitroaniline Chemical compound C1CN(CCCC)CCN1C1=CC=C([N+]([O-])=O)C(NCC=2C=CC=CC=2)=C1 WHNPCQMONQGNSL-UHFFFAOYSA-N 0.000 claims description 4
- LPOIGVZLNWEGJG-UHFFFAOYSA-N n-benzyl-5-(4-methylpiperazin-1-yl)-2-nitroaniline Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(NCC=2C=CC=CC=2)=C1 LPOIGVZLNWEGJG-UHFFFAOYSA-N 0.000 claims description 4
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- 125000004429 atom Chemical group 0.000 claims description 3
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- 210000003169 central nervous system Anatomy 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- HLSPGBDTBCMRFQ-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-(4-methylpiperazin-1-yl)-2-nitroaniline Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(NCC=2C=CC(F)=CC=2)=C1 HLSPGBDTBCMRFQ-UHFFFAOYSA-N 0.000 claims description 3
- IDOVIEHVLYVZOK-UHFFFAOYSA-N n-benzyl-2-nitro-5-(4-pyridin-2-ylpiperazin-1-yl)aniline Chemical compound [O-][N+](=O)C1=CC=C(N2CCN(CC2)C=2N=CC=CC=2)C=C1NCC1=CC=CC=C1 IDOVIEHVLYVZOK-UHFFFAOYSA-N 0.000 claims description 3
- 201000000980 schizophrenia Diseases 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 101150118795 UCH2 gene Proteins 0.000 claims 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
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- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 2
- PLHTVUFOHHOCSF-UHFFFAOYSA-N 2-[5-(4-methylpiperazin-1-yl)-2-nitrophenyl]-4-phenylphthalazin-1-one Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(N2C(C3=CC=CC=C3C(C=3C=CC=CC=3)=N2)=O)=C1 PLHTVUFOHHOCSF-UHFFFAOYSA-N 0.000 claims 2
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- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 2
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- VXFJHTLURWORGX-UHFFFAOYSA-N n-[2-(2-methylphenoxy)ethyl]-2-nitro-5-piperazin-1-ylaniline Chemical compound CC1=CC=CC=C1OCCNC1=CC(N2CCNCC2)=CC=C1[N+]([O-])=O VXFJHTLURWORGX-UHFFFAOYSA-N 0.000 claims 2
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- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 2
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- NHOSMDUPJTUDCU-UHFFFAOYSA-N 1-[3-(3,5-dimethylpyrazol-1-yl)-4-nitrophenyl]-4-methylpiperazine Chemical compound C1CN(C)CCN1C1=CC=C([N+]([O-])=O)C(N2C(=CC(C)=N2)C)=C1 NHOSMDUPJTUDCU-UHFFFAOYSA-N 0.000 claims 1
- JMJWFMJOTXNCFI-UHFFFAOYSA-N 1-[3-(3,5-dimethylpyrazol-1-yl)-4-nitrophenyl]piperazine Chemical compound N1=C(C)C=C(C)N1C1=CC(N2CCNCC2)=CC=C1[N+]([O-])=O JMJWFMJOTXNCFI-UHFFFAOYSA-N 0.000 claims 1
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- UNFZPHVBNJIVHW-UHFFFAOYSA-N 2-nitro-5-piperazin-1-yl-n-(pyridin-3-ylmethyl)aniline Chemical compound [O-][N+](=O)C1=CC=C(N2CCNCC2)C=C1NCC1=CC=CN=C1 UNFZPHVBNJIVHW-UHFFFAOYSA-N 0.000 claims 1
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- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
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- 208000029078 coronary artery disease Diseases 0.000 description 1
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- 230000008025 crystallization Effects 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- KFGVRWGDTLZAAO-UHFFFAOYSA-N cyclopenta-1,3-diene dicyclohexyl(cyclopenta-1,3-dien-1-yl)phosphane iron(2+) Chemical compound [Fe++].c1cc[cH-]c1.C1CCC(CC1)P(C1CCCCC1)c1ccc[cH-]1 KFGVRWGDTLZAAO-UHFFFAOYSA-N 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
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- 238000000605 extraction Methods 0.000 description 1
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- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
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- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000002831 pharmacologic agent Substances 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
- 238000002953 preparative HPLC Methods 0.000 description 1
- TVPRCLHSULCNLV-UHFFFAOYSA-N pyridazin-3-one Chemical compound O=C1C=CC=N[N]1 TVPRCLHSULCNLV-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 108010006590 serotonin 5 receptor Proteins 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/50—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Anesthesiology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Pyrrole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04380288A EP1676842A1 (en) | 2004-12-30 | 2004-12-30 | Nitro-substituted phenyl-piperazine compounds, their preparation and use in medicaments |
| PCT/EP2005/014191 WO2006069808A2 (en) | 2004-12-30 | 2005-12-29 | Nitro-substituted phenyl-piperazine compounds, their preparation and use in medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2007007688A true MX2007007688A (es) | 2007-08-17 |
Family
ID=34931899
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2007007688A MX2007007688A (es) | 2004-12-30 | 2005-12-29 | Compuestos de fenilpiperazina nitro-sustituidos, su preparacion y uso en medicamentos. |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US20080176854A1 (enExample) |
| EP (2) | EP1676842A1 (enExample) |
| JP (1) | JP2008526706A (enExample) |
| CN (1) | CN101133042A (enExample) |
| AT (1) | ATE529415T1 (enExample) |
| CA (1) | CA2592852A1 (enExample) |
| ES (1) | ES2375817T3 (enExample) |
| MX (1) | MX2007007688A (enExample) |
| WO (1) | WO2006069808A2 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2477604A1 (en) | 2002-03-13 | 2003-09-25 | Signum Biosciences, Inc. | Modulation of protein methylation and phosphoprotein phosphate |
| US7968538B2 (en) * | 2005-01-25 | 2011-06-28 | Galenea Corp. | Substituted arylamine compounds and methods of treatment |
| US7923041B2 (en) | 2005-02-03 | 2011-04-12 | Signum Biosciences, Inc. | Compositions and methods for enhancing cognitive function |
| EP1843734A4 (en) | 2005-02-03 | 2008-09-10 | Signum Biosciences Inc | COMPOSITIONS AND METHOD FOR INTENSIFYING COGNITIVE FUNCTIONS |
| EP2020230B1 (en) | 2007-08-01 | 2011-01-19 | Laboratorios del Dr. Esteve S.A. | Combination of at least two 5-HT6-Ligands |
| CN102014897B (zh) | 2008-04-21 | 2015-08-05 | 西格纳姆生物科学公司 | 化合物、组合物和其制备方法 |
| GB201002563D0 (en) * | 2010-02-15 | 2010-03-31 | Cambridge Entpr Ltd | Compounds |
| FR2976942B1 (fr) * | 2011-06-23 | 2013-07-12 | Metabolys | Derives de piperazine, leurs procedes de preparation et leurs utilisations dans le traitement de l'insulinoresistance |
| JP5949070B2 (ja) * | 2012-04-03 | 2016-07-06 | Jsr株式会社 | 液晶配向剤、液晶配向膜及び液晶表示素子 |
| HK1215256A1 (zh) | 2012-11-20 | 2016-08-19 | Vertex Pharmaceuticals Incorporated | 用作吲哚胺2，3-二氧化酶的抑制劑的化合物 |
| US11459308B2 (en) | 2016-12-05 | 2022-10-04 | Microbiotix, Inc. | Broad spectrum inhibitors of filoviruses |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2712591B1 (fr) * | 1993-11-19 | 1996-02-09 | Pf Medicament | Nouvelles arylpipérazines dérivées d'indole, leur préparation et leur utilisation thérapeutique. |
| JP4597480B2 (ja) * | 2001-05-11 | 2010-12-15 | プロキシマゲン・リミテッド | 肥満、ｉｉ型糖尿病およびｃｎｓ疾患の処置のための新規アリールスルホンアミド化合物 |
| EP1412325A1 (en) * | 2001-06-11 | 2004-04-28 | Biovitrum Ab | Substituted sulfonamide compounds, process for their use as medicament for the treatment of cns disorders, obesity and type ii diabetes |
| GB0305575D0 (en) * | 2003-03-11 | 2003-04-16 | Glaxo Group Ltd | Novel compounds |
| US8362264B2 (en) * | 2003-08-22 | 2013-01-29 | Dendreon Corporation | Compositions and methods for the treatment of disease associated with Trp-p8 expression |
| ATE437864T1 (de) * | 2004-10-22 | 2009-08-15 | Janssen Pharmaceutica Nv | Aromatische amide als hemmer der c-fms-kinase |
| US7968538B2 (en) * | 2005-01-25 | 2011-06-28 | Galenea Corp. | Substituted arylamine compounds and methods of treatment |
-
2004
- 2004-12-30 EP EP04380288A patent/EP1676842A1/en not_active Withdrawn
-
2005
- 2005-12-29 ES ES05824122T patent/ES2375817T3/es not_active Expired - Lifetime
- 2005-12-29 JP JP2007548771A patent/JP2008526706A/ja active Pending
- 2005-12-29 MX MX2007007688A patent/MX2007007688A/es not_active Application Discontinuation
- 2005-12-29 AT AT05824122T patent/ATE529415T1/de not_active IP Right Cessation
- 2005-12-29 CA CA002592852A patent/CA2592852A1/en not_active Abandoned
- 2005-12-29 WO PCT/EP2005/014191 patent/WO2006069808A2/en not_active Ceased
- 2005-12-29 US US11/813,247 patent/US20080176854A1/en not_active Abandoned
- 2005-12-29 CN CNA2005800488245A patent/CN101133042A/zh active Pending
- 2005-12-29 EP EP05824122A patent/EP1851210B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| ES2375817T3 (es) | 2012-03-06 |
| EP1851210A2 (en) | 2007-11-07 |
| US20080176854A1 (en) | 2008-07-24 |
| WO2006069808A2 (en) | 2006-07-06 |
| EP1676842A1 (en) | 2006-07-05 |
| CN101133042A (zh) | 2008-02-27 |
| ATE529415T1 (de) | 2011-11-15 |
| JP2008526706A (ja) | 2008-07-24 |
| CA2592852A1 (en) | 2006-07-06 |
| EP1851210B1 (en) | 2011-10-19 |
| WO2006069808A3 (en) | 2006-11-02 |
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