JP2008526705A5 - - Google Patents
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- JP2008526705A5 JP2008526705A5 JP2007548770A JP2007548770A JP2008526705A5 JP 2008526705 A5 JP2008526705 A5 JP 2008526705A5 JP 2007548770 A JP2007548770 A JP 2007548770A JP 2007548770 A JP2007548770 A JP 2007548770A JP 2008526705 A5 JP2008526705 A5 JP 2008526705A5
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- JP
- Japan
- Prior art keywords
- alkyl
- group
- phenyl
- radical
- butyl
- 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.)
- Pending
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- -1 alicyclic radicals Chemical class 0.000 claims 137
- 229910052801 chlorine Inorganic materials 0.000 claims 88
- 239000000460 chlorine Substances 0.000 claims 84
- 229910052794 bromium Inorganic materials 0.000 claims 83
- 229910052731 fluorine Inorganic materials 0.000 claims 81
- 229910052740 iodine Inorganic materials 0.000 claims 75
- 125000001424 substituent group Chemical group 0.000 claims 72
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 59
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 47
- 125000003118 aryl group Chemical group 0.000 claims 44
- 150000001875 compounds Chemical class 0.000 claims 40
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 35
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 35
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 35
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 35
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 34
- 150000005840 aryl radicals Chemical class 0.000 claims 31
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 28
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 28
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 28
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 28
- 125000002541 furyl group Chemical group 0.000 claims 26
- 125000001544 thienyl group Chemical group 0.000 claims 26
- 125000005842 heteroatom Chemical group 0.000 claims 24
- 125000001624 naphthyl group Chemical group 0.000 claims 22
- 229910052757 nitrogen Inorganic materials 0.000 claims 21
- 239000012429 reaction media Substances 0.000 claims 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 14
- 229910052760 oxygen Inorganic materials 0.000 claims 14
- 239000001301 oxygen Substances 0.000 claims 14
- 229920006395 saturated elastomer Polymers 0.000 claims 14
- 239000011593 sulfur Substances 0.000 claims 14
- 229910052717 sulfur Inorganic materials 0.000 claims 14
- 125000000335 thiazolyl group Chemical group 0.000 claims 14
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims 13
- 125000006239 protecting group Chemical group 0.000 claims 13
- 230000002265 prevention Effects 0.000 claims 11
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 10
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims 10
- 125000004122 cyclic group Chemical group 0.000 claims 10
- 125000002883 imidazolyl group Chemical group 0.000 claims 10
- 238000006467 substitution reaction Methods 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 9
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 9
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 8
- 125000000842 isoxazolyl group Chemical group 0.000 claims 8
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 8
- 125000002971 oxazolyl group Chemical group 0.000 claims 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims 8
- 125000002098 pyridazinyl group Chemical group 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 8
- 125000000168 pyrrolyl group Chemical group 0.000 claims 8
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 8
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 8
- 125000000464 thioxo group Chemical group S=* 0.000 claims 8
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 7
- 239000003054 catalyst Substances 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 7
- 125000005874 benzothiadiazolyl group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000001786 isothiazolyl group Chemical group 0.000 claims 6
- 150000003254 radicals Chemical class 0.000 claims 6
- 125000001425 triazolyl group Chemical group 0.000 claims 6
- WFZFZXACWWMWPM-UHFFFAOYSA-N 2-(benzylamino)-4-(4-methylpiperazin-1-yl)benzoic acid Chemical compound C1CN(C)CCN1C1=CC=C(C(O)=O)C(NCC=2C=CC=CC=2)=C1 WFZFZXACWWMWPM-UHFFFAOYSA-N 0.000 claims 5
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 5
- 125000004429 atom Chemical group 0.000 claims 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 5
- 239000003795 chemical substances by application Substances 0.000 claims 5
- 208000035475 disorder Diseases 0.000 claims 5
- 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 4
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 4
- 208000008589 Obesity Diseases 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 125000002723 alicyclic group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 239000012752 auxiliary agent Substances 0.000 claims 4
- 125000003725 azepanyl group Chemical group 0.000 claims 4
- 125000002393 azetidinyl group Chemical group 0.000 claims 4
- 125000004069 aziridinyl group Chemical group 0.000 claims 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 230000019771 cognition Effects 0.000 claims 4
- 208000010877 cognitive disease Diseases 0.000 claims 4
- 230000001149 cognitive effect Effects 0.000 claims 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 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 4
- 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 4
- 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 4
- 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 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 4
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 4
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 4
- 125000002757 morpholinyl group Chemical group 0.000 claims 4
- 235000020824 obesity Nutrition 0.000 claims 4
- 125000004193 piperazinyl group Chemical group 0.000 claims 4
- 125000003386 piperidinyl group Chemical group 0.000 claims 4
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 4
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 4
- MDIHEDNCIGRDGU-UHFFFAOYSA-N 4-(4-methylpiperazin-1-yl)-2-(2-phenylethylamino)benzoic acid Chemical compound C1CN(C)CCN1C1=CC=C(C(O)=O)C(NCCC=2C=CC=CC=2)=C1 MDIHEDNCIGRDGU-UHFFFAOYSA-N 0.000 claims 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 3
- 208000024827 Alzheimer disease Diseases 0.000 claims 3
- 208000032841 Bulimia Diseases 0.000 claims 3
- 206010006550 Bulimia nervosa Diseases 0.000 claims 3
- 208000028698 Cognitive impairment Diseases 0.000 claims 3
- 208000018737 Parkinson disease Diseases 0.000 claims 3
- 208000028017 Psychotic disease Diseases 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- 239000012453 solvate Substances 0.000 claims 3
- HZHGVNZFZLEQOX-UHFFFAOYSA-N 2-(benzylamino)-4-(4-methylpiperazin-1-yl)benzonitrile Chemical compound C1CN(C)CCN1C1=CC=C(C#N)C(NCC=2C=CC=CC=2)=C1 HZHGVNZFZLEQOX-UHFFFAOYSA-N 0.000 claims 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical class [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims 2
- 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 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 206010006895 Cachexia Diseases 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- 206010010904 Convulsion Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 206010019196 Head injury Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 206010021143 Hypoxia Diseases 0.000 claims 2
- 208000019695 Migraine disease Diseases 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- 208000021384 Obsessive-Compulsive disease Diseases 0.000 claims 2
- 206010033664 Panic attack Diseases 0.000 claims 2
- 206010039966 Senile dementia Diseases 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 208000022531 anorexia Diseases 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 230000001684 chronic effect Effects 0.000 claims 2
- 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
- 230000036461 convulsion Effects 0.000 claims 2
- 206010061428 decreased appetite Diseases 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 206010013663 drug dependence Diseases 0.000 claims 2
- 230000002708 enhancing effect Effects 0.000 claims 2
- 206010015037 epilepsy Diseases 0.000 claims 2
- 230000037406 food intake Effects 0.000 claims 2
- 235000012631 food intake Nutrition 0.000 claims 2
- 208000013403 hyperactivity Diseases 0.000 claims 2
- 230000007954 hypoxia Effects 0.000 claims 2
- 206010027599 migraine Diseases 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 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 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 208000019906 panic disease Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 208000019116 sleep disease Diseases 0.000 claims 2
- 208000020685 sleep-wake disease Diseases 0.000 claims 2
- 208000011117 substance-related disease Diseases 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 claims 1
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 1
- CBYSIJBEUWAVAA-UHFFFAOYSA-N 2-(furan-2-ylmethylamino)-4-(4-methylpiperazin-1-yl)benzoic acid Chemical compound C1CN(C)CCN1C1=CC=C(C(O)=O)C(NCC=2OC=CC=2)=C1 CBYSIJBEUWAVAA-UHFFFAOYSA-N 0.000 claims 1
- HHJORYDAHSBCPD-UHFFFAOYSA-N 2-(furan-2-ylmethylamino)-4-(4-methylpiperazin-1-yl)benzonitrile Chemical compound C1CN(C)CCN1C1=CC=C(C#N)C(NCC=2OC=CC=2)=C1 HHJORYDAHSBCPD-UHFFFAOYSA-N 0.000 claims 1
- JXZVCMWWCLKOND-UHFFFAOYSA-N 2-methoxy-5-(4-methylpiperazin-1-yl)-n-(2-phenylethyl)aniline Chemical compound COC1=CC=C(N2CCN(C)CC2)C=C1NCCC1=CC=CC=C1 JXZVCMWWCLKOND-UHFFFAOYSA-N 0.000 claims 1
- ULBWRSOPHKGYLP-UHFFFAOYSA-N 5-(4-methylpiperazin-1-yl)-2-phenylmethoxyaniline Chemical compound C1CN(C)CCN1C(C=C1N)=CC=C1OCC1=CC=CC=C1 ULBWRSOPHKGYLP-UHFFFAOYSA-N 0.000 claims 1
- QFZMKTVOJUEHMG-UHFFFAOYSA-N 5-(4-methylpiperazin-1-yl)-n-(2-phenylethyl)-2-phenylmethoxyaniline Chemical compound C1CN(C)CCN1C(C=C1NCCC=2C=CC=CC=2)=CC=C1OCC1=CC=CC=C1 QFZMKTVOJUEHMG-UHFFFAOYSA-N 0.000 claims 1
- 208000007848 Alcoholism Diseases 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 206010012335 Dependence Diseases 0.000 claims 1
- 208000026139 Memory disease Diseases 0.000 claims 1
- IHULFCDGFFJLLK-UHFFFAOYSA-N N-methyl-N-[5-(4-methylpiperazin-1-yl)-2-phenylmethoxyphenyl]furan-2-amine Chemical compound C=1C(N2CCN(C)CC2)=CC=C(OCC=2C=CC=CC=2)C=1N(C)C1=CC=CO1 IHULFCDGFFJLLK-UHFFFAOYSA-N 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 206010057852 Nicotine dependence Diseases 0.000 claims 1
- 208000025569 Tobacco Use disease Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 235000021229 appetite regulation Nutrition 0.000 claims 1
- 229940049706 benzodiazepine Drugs 0.000 claims 1
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- 230000037396 body weight Effects 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 229960003920 cocaine Drugs 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- 238000012423 maintenance Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 206010027175 memory impairment Diseases 0.000 claims 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims 1
- WFOLZSRGLJHBCN-UHFFFAOYSA-N methyl 2-(benzylamino)-4-(4-methylpiperazin-1-yl)benzoate Chemical compound COC(=O)C1=CC=C(N2CCN(C)CC2)C=C1NCC1=CC=CC=C1 WFOLZSRGLJHBCN-UHFFFAOYSA-N 0.000 claims 1
- ASJVRMMOPQBABY-UHFFFAOYSA-N methyl 2-(furan-2-ylmethylamino)-4-(4-methylpiperazin-1-yl)benzoate Chemical compound COC(=O)C1=CC=C(N2CCN(C)CC2)C=C1NCC1=CC=CO1 ASJVRMMOPQBABY-UHFFFAOYSA-N 0.000 claims 1
- JXFNOYWXKCDHGQ-UHFFFAOYSA-N methyl 4-(4-methylpiperazin-1-yl)-2-(2-phenylethylamino)benzoate Chemical compound COC(=O)C1=CC=C(N2CCN(C)CC2)C=C1NCCC1=CC=CC=C1 JXFNOYWXKCDHGQ-UHFFFAOYSA-N 0.000 claims 1
- WOIXBPIABHLZAY-UHFFFAOYSA-N n-(furan-2-ylmethyl)-2-methoxy-5-(4-methylpiperazin-1-yl)aniline Chemical compound COC1=CC=C(N2CCN(C)CC2)C=C1NCC1=CC=CO1 WOIXBPIABHLZAY-UHFFFAOYSA-N 0.000 claims 1
- BKYYCKTXIMUECZ-UHFFFAOYSA-N n-[2-(3,5-dimethylpyrazol-1-yl)-4-(4-methylpiperazin-1-yl)phenyl]acetamide Chemical compound C1CN(C)CCN1C1=CC=C(NC(C)=O)C(N2C(=CC(C)=N2)C)=C1 BKYYCKTXIMUECZ-UHFFFAOYSA-N 0.000 claims 1
- ZYOWFEBTYNZXLF-UHFFFAOYSA-N n-[2-(benzylamino)-4-(4-methylpiperazin-1-yl)phenyl]acetamide Chemical compound C1CN(C)CCN1C1=CC=C(NC(C)=O)C(NCC=2C=CC=CC=2)=C1 ZYOWFEBTYNZXLF-UHFFFAOYSA-N 0.000 claims 1
- ADICJNUDACADIN-UHFFFAOYSA-N n-[2-(benzylamino)-4-(4-methylpiperazin-1-yl)phenyl]benzenesulfonamide Chemical compound C1CN(C)CCN1C(C=C1NCC=2C=CC=CC=2)=CC=C1NS(=O)(=O)C1=CC=CC=C1 ADICJNUDACADIN-UHFFFAOYSA-N 0.000 claims 1
- SNUBWJKPSBHZOH-UHFFFAOYSA-N n-[2-(benzylamino)-4-(4-methylpiperazin-1-yl)phenyl]methanesulfonamide Chemical compound C1CN(C)CCN1C1=CC=C(NS(C)(=O)=O)C(NCC=2C=CC=CC=2)=C1 SNUBWJKPSBHZOH-UHFFFAOYSA-N 0.000 claims 1
- SPPYXPYZXSWNEF-UHFFFAOYSA-N n-[2-[acetyl(benzyl)amino]-5-(4-methylpiperazin-1-yl)phenyl]acetamide Chemical compound C1CN(C)CCN1C(C=C1NC(C)=O)=CC=C1N(C(C)=O)CC1=CC=CC=C1 SPPYXPYZXSWNEF-UHFFFAOYSA-N 0.000 claims 1
- SNJGTPYBEMEVRH-UHFFFAOYSA-N n-[2-[acetyl(furan-2-ylmethyl)amino]-4-(4-methylpiperazin-1-yl)phenyl]acetamide Chemical compound C1CN(C)CCN1C1=CC=C(NC(C)=O)C(N(CC=2OC=CC=2)C(C)=O)=C1 SNJGTPYBEMEVRH-UHFFFAOYSA-N 0.000 claims 1
- WYGBQZUNBWZIRS-UHFFFAOYSA-N n-[2-amino-4-(4-methylpiperazin-1-yl)phenyl]-n-benzylacetamide Chemical compound C1CN(C)CCN1C(C=C1N)=CC=C1N(C(C)=O)CC1=CC=CC=C1 WYGBQZUNBWZIRS-UHFFFAOYSA-N 0.000 claims 1
- GVZQKYQJXVHCLO-UHFFFAOYSA-N n-[2-amino-5-(4-methylpiperazin-1-yl)phenyl]-n-(furan-2-ylmethyl)acetamide Chemical compound C1CN(C)CCN1C1=CC=C(N)C(N(CC=2OC=CC=2)C(C)=O)=C1 GVZQKYQJXVHCLO-UHFFFAOYSA-N 0.000 claims 1
- HFERBEZYFLCFDW-UHFFFAOYSA-N n-[4-(4-methylpiperazin-1-yl)-2-(2-phenoxyethylamino)phenyl]acetamide Chemical compound C1CN(C)CCN1C1=CC=C(NC(C)=O)C(NCCOC=2C=CC=CC=2)=C1 HFERBEZYFLCFDW-UHFFFAOYSA-N 0.000 claims 1
- XMRHNDHBZFNIMG-UHFFFAOYSA-N n-benzyl-2-methoxy-5-(4-methylpiperazin-1-yl)aniline Chemical compound COC1=CC=C(N2CCN(C)CC2)C=C1NCC1=CC=CC=C1 XMRHNDHBZFNIMG-UHFFFAOYSA-N 0.000 claims 1
- RDPPMOCXKWPZLB-UHFFFAOYSA-N n-benzyl-4-(4-methylpiperazin-1-yl)-2-nitroaniline Chemical compound C1CN(C)CCN1C(C=C1[N+]([O-])=O)=CC=C1NCC1=CC=CC=C1 RDPPMOCXKWPZLB-UHFFFAOYSA-N 0.000 claims 1
- KGACXFRDNFTJOU-UHFFFAOYSA-N n-benzyl-5-(4-methylpiperazin-1-yl)-2-phenylmethoxyaniline Chemical compound C1CN(C)CCN1C(C=C1NCC=2C=CC=CC=2)=CC=C1OCC1=CC=CC=C1 KGACXFRDNFTJOU-UHFFFAOYSA-N 0.000 claims 1
- 229960002715 nicotine Drugs 0.000 claims 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 1
- 229940005483 opioid analgesics Drugs 0.000 claims 1
- 230000003893 regulation of appetite Effects 0.000 claims 1
- UQFQONCQIQEYPJ-UHFFFAOYSA-N C[n]1nccc1 Chemical compound C[n]1nccc1 UQFQONCQIQEYPJ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04380289A EP1695971A1 (en) | 2004-12-30 | 2004-12-30 | Substituted phenyl-piperazine compounds, their preparation and use in medicaments |
| PCT/EP2005/014190 WO2006069807A1 (en) | 2004-12-30 | 2005-12-29 | Substituted phenyl-piperazine compounds, their preparation and use in medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2008526705A JP2008526705A (ja) | 2008-07-24 |
| JP2008526705A5 true JP2008526705A5 (enExample) | 2009-02-05 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007548770A Pending JP2008526705A (ja) | 2004-12-30 | 2005-12-29 | 置換フェニル−ピペラジン化合物、それらの調製および薬剤における使用 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US20090042904A1 (enExample) |
| EP (2) | EP1695971A1 (enExample) |
| JP (1) | JP2008526705A (enExample) |
| CN (1) | CN101142201A (enExample) |
| CA (1) | CA2592832A1 (enExample) |
| MX (1) | MX2007007684A (enExample) |
| WO (1) | WO2006069807A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5186219B2 (ja) | 2005-01-25 | 2013-04-17 | エピックス デラウェア， インコーポレイテッド | 置換アリールアミン化合物および５−ｈｔ６調節因子としてのその使用 |
| EP1878724A1 (en) | 2006-07-15 | 2008-01-16 | sanofi-aventis | A regioselective palladium catalyzed synthesis of benzimidazoles and azabenzimidazoles |
| EP1902733A1 (en) * | 2006-09-19 | 2008-03-26 | Laboratorios Del Dr. Esteve, S.A. | Combination of a NMDA-receptor ligand and a compound with 5-HT6 receptor affinity |
| ES2358288T3 (es) | 2007-08-01 | 2011-05-09 | Laboratorios Del Dr. Esteve S.A. | Combinación de al menos dos ligandos de 5ht6. |
| WO2009079797A1 (en) | 2007-12-26 | 2009-07-02 | Critical Outcome Technologies, Inc. | Compounds and method for treatment of cancer |
| EP3023426A1 (en) | 2008-07-17 | 2016-05-25 | Critical Outcome Technologies, Inc. | Thiosemicarbazone inhibitor compounds and cancer treatment methods |
| US8420640B2 (en) * | 2008-08-29 | 2013-04-16 | Treventis Corporation | Methods of treating amyloid disease using analogs of 1-(4-nitrophenyl) piperazine |
| GB0815781D0 (en) * | 2008-08-29 | 2008-10-08 | Xention Ltd | Novel potassium channel blockers |
| WO2011120153A1 (en) | 2010-04-01 | 2011-10-06 | Critical Outcome Technologies Inc. | Compounds and method for treatment of hiv |
| WO2015158313A1 (en) | 2014-04-19 | 2015-10-22 | Sunshine Lake Pharma Co., Ltd. | Sulfonamide derivatives and pharmaceutical applications thereof |
| GB201521919D0 (en) * | 2015-12-11 | 2016-01-27 | Electrophoretics Ltd | Isobaric mass labels |
| WO2018106667A1 (en) | 2016-12-05 | 2018-06-14 | Microbiotix, Inc. | Broad-spectrum inhibitors of filoviruses |
| RU2676100C1 (ru) * | 2018-10-05 | 2018-12-26 | федеральное государственное автономное образовательное учреждение высшего образования "Санкт-Петербургский политехнический университет Петра Великого" (ФГАОУ ВО "СПбПУ") | Применение производных пиперазина для лечения болезни Альцгеймера и деменций альцгеймеровского типа с нарушенной внутриклеточной кальциевой сигнализацией |
| CN109799297A (zh) * | 2019-02-01 | 2019-05-24 | 广西中烟工业有限责任公司 | 一种卷烟烟气pH调控模型的构建方法及其调控方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19637237A1 (de) * | 1996-09-13 | 1998-03-19 | Merck Patent Gmbh | Piperazin-Derivate |
| EP0994862B1 (en) * | 1997-07-11 | 2005-06-01 | SmithKline Beecham plc | Sulphonamide derivatives being 5-ht6 receptor antagonists and process for their preparation |
| NZ528450A (en) * | 2001-05-11 | 2006-02-24 | Biovitrum Ab | Novel, arylsulfonamide compounds for the treatment of obesity, type II diabetes and CNS-disorders |
| ES2316619T3 (es) * | 2001-08-10 | 2009-04-16 | F. Hoffmann-La Roche Ag | Derivados de arilsulfonilo con afinidad receptora de 5-ht 6. |
-
2004
- 2004-12-30 EP EP04380289A patent/EP1695971A1/en not_active Withdrawn
-
2005
- 2005-12-29 JP JP2007548770A patent/JP2008526705A/ja active Pending
- 2005-12-29 US US11/813,161 patent/US20090042904A1/en not_active Abandoned
- 2005-12-29 CA CA002592832A patent/CA2592832A1/en not_active Abandoned
- 2005-12-29 CN CNA2005800488279A patent/CN101142201A/zh active Pending
- 2005-12-29 WO PCT/EP2005/014190 patent/WO2006069807A1/en not_active Ceased
- 2005-12-29 MX MX2007007684A patent/MX2007007684A/es not_active Application Discontinuation
- 2005-12-29 EP EP05825004A patent/EP1844031A1/en not_active Withdrawn
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