BRPI0718520A2

BRPI0718520A2 - Composto, métodos para a modulação do receptor de adenosina a1 e para o tratamento de condições mediadas pelo receptor de adenosina a1 em mamíferos, composição farmacêutica, e, usos de uma composição e de um composto

Composto, métodos para a modulação do receptor de adenosina a1 e para o tratamento de condições mediadas pelo receptor de adenosina a1 em mamíferos, composição farmacêutica, e, usos de uma composição e de um composto Download PDF

Info

Publication number: BRPI0718520A2
Authority: BR; Brazil
Prior art keywords: chlorophenyl; amino; methyl; methanone; thiophen
Prior art date: 2006-11-13

Application number

BRPI0718520-0A

Other languages

English (en)

Portuguese (pt)

Inventor

Pier Giovanni Baraldi

Allan R Moorman

Romeo Romagnoli

Original Assignee

King Pharmaceuticals Res & Dev

Priority date

2006-11-13

Filing date

2007-11-13

Publication date

2013-11-19

2007-11-12 Priority claimed from US11/938,465 external-priority patent/US7855209B2/en

2007-11-12 Priority claimed from US11/938,514 external-priority patent/US7897596B2/en

2007-11-13 Application filed by King Pharmaceuticals Res & Dev filed Critical King Pharmaceuticals Res & Dev

2013-11-19 Publication of BRPI0718520A2 publication Critical patent/BRPI0718520A2/pt

Links

150000001875 compounds Chemical class 0.000 title claims description 282
239000008194 pharmaceutical composition Substances 0.000 title claims description 29
238000011282 treatment Methods 0.000 title claims description 26
230000001404 mediated effect Effects 0.000 title claims description 15
108010060263 Adenosine A1 Receptor Proteins 0.000 title claims description 12
102000030814 Adenosine A1 receptor Human genes 0.000 title claims description 12
239000000203 mixture Substances 0.000 title description 58
238000000034 method Methods 0.000 title description 33
OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 title description 14
241000124008 Mammalia Species 0.000 title description 11
239000002126 C01EB10 - Adenosine Substances 0.000 title description 7
229960005305 adenosine Drugs 0.000 title description 7
-1 (4-fluorophenyl) piperazin-1-yl Chemical group 0.000 claims description 119
150000003839 salts Chemical class 0.000 claims description 99
229910052739 hydrogen Inorganic materials 0.000 claims description 89
125000000217 alkyl group Chemical group 0.000 claims description 87
239000001257 hydrogen Substances 0.000 claims description 87
125000003118 aryl group Chemical group 0.000 claims description 61
150000002431 hydrogen Chemical group 0.000 claims description 53
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 52
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 48
229910052736 halogen Inorganic materials 0.000 claims description 44
150000002367 halogens Chemical class 0.000 claims description 44
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 44
125000004093 cyano group Chemical group *C#N 0.000 claims description 41
125000003107 substituted aryl group Chemical group 0.000 claims description 39
125000000753 cycloalkyl group Chemical group 0.000 claims description 38
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
208000002193 Pain Diseases 0.000 claims description 32
125000000547 substituted alkyl group Chemical group 0.000 claims description 32
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 28
150000001721 carbon Chemical group 0.000 claims description 24
229910052799 carbon Inorganic materials 0.000 claims description 24
230000036407 pain Effects 0.000 claims description 23
125000003545 alkoxy group Chemical group 0.000 claims description 22
AVPYQKSLYISFPO-UHFFFAOYSA-N 4-chlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1 AVPYQKSLYISFPO-UHFFFAOYSA-N 0.000 claims description 21
125000002252 acyl group Chemical group 0.000 claims description 19
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 17
239000003814 drug Substances 0.000 claims description 17
125000001072 heteroaryl group Chemical group 0.000 claims description 16
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
208000004296 neuralgia Diseases 0.000 claims description 15
208000021722 neuropathic pain Diseases 0.000 claims description 15
125000004475 heteroaralkyl group Chemical group 0.000 claims description 14
229910052760 oxygen Inorganic materials 0.000 claims description 14
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 13
239000001301 oxygen Substances 0.000 claims description 13
229910052717 sulfur Chemical group 0.000 claims description 13
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 12
239000011593 sulfur Chemical group 0.000 claims description 11
208000019622 heart disease Diseases 0.000 claims description 10
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 9
208000035475 disorder Diseases 0.000 claims description 9
206010015037 epilepsy Diseases 0.000 claims description 9
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
208000019116 sleep disease Diseases 0.000 claims description 9
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 8
125000005605 benzo group Chemical group 0.000 claims description 6
230000006378 damage Effects 0.000 claims description 6
125000005415 substituted alkoxy group Chemical group 0.000 claims description 6
WBVSHKCZLDSJBP-UHFFFAOYSA-N [2-amino-4-[(4-phenylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=CC=C1 WBVSHKCZLDSJBP-UHFFFAOYSA-N 0.000 claims description 5
ZJXZMWGZHYTTGI-UHFFFAOYSA-N [2-amino-5-phenyl-4-(piperidin-1-ylmethyl)thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC(C=2C=CC=CC=2)=C1CN1CCCCC1 ZJXZMWGZHYTTGI-UHFFFAOYSA-N 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
BTURCFCECILJTE-UHFFFAOYSA-N 2-[4-[[5-amino-4-(4-chlorobenzoyl)thiophen-3-yl]methyl]piperazin-1-yl]-1-(4-chlorophenyl)ethanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1CC(=O)C1=CC=C(Cl)C=C1 BTURCFCECILJTE-UHFFFAOYSA-N 0.000 claims description 2
GBEKMUYDTMZKOO-UHFFFAOYSA-N 4-[4-[[5-amino-4-(4-chlorobenzoyl)thiophen-3-yl]methyl]piperazin-1-yl]benzonitrile Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=C(C#N)C=C1 GBEKMUYDTMZKOO-UHFFFAOYSA-N 0.000 claims description 2
HYXHXEHHOZDASV-UHFFFAOYSA-N [2-amino-4-[(4-benzylpiperazin-1-yl)methyl]-5-methylthiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C1CN(CC=2C=CC=CC=2)CCN1CC1=C(C)SC(N)=C1C(=O)C1=CC=C(Cl)C=C1 HYXHXEHHOZDASV-UHFFFAOYSA-N 0.000 claims description 2
VLUIIUMESZDQJJ-UHFFFAOYSA-N [2-amino-4-[(4-benzylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1CC1=CC=CC=C1 VLUIIUMESZDQJJ-UHFFFAOYSA-N 0.000 claims description 2
PNTFMBLZDHRWEH-UHFFFAOYSA-N [2-amino-4-[(4-cyclohexylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1CCCCC1 PNTFMBLZDHRWEH-UHFFFAOYSA-N 0.000 claims description 2
GZDAZWLRSGSJFO-UHFFFAOYSA-N [2-amino-4-[(4-cyclooctylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1CCCCCCC1 GZDAZWLRSGSJFO-UHFFFAOYSA-N 0.000 claims description 2
FBLJFWZLJFATLC-UHFFFAOYSA-N [2-amino-4-[(4-methylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C1CN(C)CCN1CC1=CSC(N)=C1C(=O)C1=CC=C(Cl)C=C1 FBLJFWZLJFATLC-UHFFFAOYSA-N 0.000 claims description 2
LRNXGDCNTQAXDV-UHFFFAOYSA-N [2-amino-4-[(4-pyridin-2-ylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=CC=N1 LRNXGDCNTQAXDV-UHFFFAOYSA-N 0.000 claims description 2
PTDILEGANSBTSE-UHFFFAOYSA-N [2-amino-4-[(4-pyridin-4-ylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=NC=C1 PTDILEGANSBTSE-UHFFFAOYSA-N 0.000 claims description 2
FJHGONQMXVSBES-UHFFFAOYSA-N [2-amino-4-[(4-pyrimidin-2-ylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=NC=CC=N1 FJHGONQMXVSBES-UHFFFAOYSA-N 0.000 claims description 2
BKVQQVAZXXNRAL-UHFFFAOYSA-N [2-amino-4-[[2-(4-chlorophenyl)-2,5-diazabicyclo[2.2.1]heptan-5-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN1CC2CC1CN2C1=CC=C(Cl)C=C1 BKVQQVAZXXNRAL-UHFFFAOYSA-N 0.000 claims description 2
BRWGCTMCYZVICL-UHFFFAOYSA-N [2-amino-4-[[4-(2,3-dichlorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=CC(Cl)=C1Cl BRWGCTMCYZVICL-UHFFFAOYSA-N 0.000 claims description 2
QLXKABIMWDIRKB-UHFFFAOYSA-N [2-amino-4-[[4-(2,4,6-trifluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=C(F)C=C(F)C=C1F QLXKABIMWDIRKB-UHFFFAOYSA-N 0.000 claims description 2
RLQCJMVZVOGKBW-UHFFFAOYSA-N [2-amino-4-[[4-(2,4-dichlorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=C(Cl)C=C1Cl RLQCJMVZVOGKBW-UHFFFAOYSA-N 0.000 claims description 2
RRXKFDQOOZHJTF-UHFFFAOYSA-N [2-amino-4-[[4-(2,5-dichlorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC(Cl)=CC=C1Cl RRXKFDQOOZHJTF-UHFFFAOYSA-N 0.000 claims description 2
BHNZEYVIYRIQCZ-UHFFFAOYSA-N [2-amino-4-[[4-(2,6-dichlorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=C(Cl)C=CC=C1Cl BHNZEYVIYRIQCZ-UHFFFAOYSA-N 0.000 claims description 2
DHAUTGJWCQUFII-UHFFFAOYSA-N [2-amino-4-[[4-(2,6-difluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=C(F)C=CC=C1F DHAUTGJWCQUFII-UHFFFAOYSA-N 0.000 claims description 2
HDQFEKGOVIJERJ-UHFFFAOYSA-N [2-amino-4-[[4-(2,6-difluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=CC(C(F)(F)F)=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=C(F)C=CC=C1F HDQFEKGOVIJERJ-UHFFFAOYSA-N 0.000 claims description 2
KFWAXNAVBQKIAZ-UHFFFAOYSA-N [2-amino-4-[[4-(2-fluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=CC=C1F KFWAXNAVBQKIAZ-UHFFFAOYSA-N 0.000 claims description 2
NQOCPHPCHPECPX-UHFFFAOYSA-N [2-amino-4-[[4-(3,4-dichlorophenyl)piperazin-1-yl]methyl]-5-methylthiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C1CN(C=2C=C(Cl)C(Cl)=CC=2)CCN1CC1=C(C)SC(N)=C1C(=O)C1=CC=C(Cl)C=C1 NQOCPHPCHPECPX-UHFFFAOYSA-N 0.000 claims description 2
HZIBFSCCTZORDE-UHFFFAOYSA-N [2-amino-4-[[4-(3,4-dichlorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=C(Cl)C(Cl)=C1 HZIBFSCCTZORDE-UHFFFAOYSA-N 0.000 claims description 2
RQMCCXLNHOFIBT-UHFFFAOYSA-N [2-amino-4-[[4-(3,4-difluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=C(F)C(F)=C1 RQMCCXLNHOFIBT-UHFFFAOYSA-N 0.000 claims description 2
ACGNVIYHWCNNLW-UHFFFAOYSA-N [2-amino-4-[[4-(3,5-dichlorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC(Cl)=CC(Cl)=C1 ACGNVIYHWCNNLW-UHFFFAOYSA-N 0.000 claims description 2
UFSBQTGZKIHMDQ-UHFFFAOYSA-N [2-amino-4-[[4-(3,5-difluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC(F)=CC(F)=C1 UFSBQTGZKIHMDQ-UHFFFAOYSA-N 0.000 claims description 2
KFWLBGALSCQPIL-UHFFFAOYSA-N [2-amino-4-[[4-(3-chloro-4-fluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=C(F)C(Cl)=C1 KFWLBGALSCQPIL-UHFFFAOYSA-N 0.000 claims description 2
WERJSQBLFNLURF-UHFFFAOYSA-N [2-amino-4-[[4-(3-chlorophenyl)piperazin-1-yl]methyl]-5-methylthiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C1CN(C=2C=C(Cl)C=CC=2)CCN1CC1=C(C)SC(N)=C1C(=O)C1=CC=C(Cl)C=C1 WERJSQBLFNLURF-UHFFFAOYSA-N 0.000 claims description 2
NDWVFXKAKMRXDA-UHFFFAOYSA-N [2-amino-4-[[4-(3-chlorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=CC(Cl)=C1 NDWVFXKAKMRXDA-UHFFFAOYSA-N 0.000 claims description 2
ALBMIWSWBYYXEY-UHFFFAOYSA-N [2-amino-4-[[4-(3-fluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=CC(F)=C1 ALBMIWSWBYYXEY-UHFFFAOYSA-N 0.000 claims description 2
MMICKMTWNXSUED-UHFFFAOYSA-N [2-amino-4-[[4-(4-bromophenyl)piperazin-1-yl]methyl]-5-methylthiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C1CN(C=2C=CC(Br)=CC=2)CCN1CC1=C(C)SC(N)=C1C(=O)C1=CC=C(Cl)C=C1 MMICKMTWNXSUED-UHFFFAOYSA-N 0.000 claims description 2
DFDQPGWWASNUFZ-UHFFFAOYSA-N [2-amino-4-[[4-(4-chlorobenzoyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C(=O)C1=CC=C(Cl)C=C1 DFDQPGWWASNUFZ-UHFFFAOYSA-N 0.000 claims description 2
YTSDAHZZAZSJJB-UHFFFAOYSA-N [2-amino-4-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-5-ethylthiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C1CN(C=2C=CC(Cl)=CC=2)CCN1CC1=C(CC)SC(N)=C1C(=O)C1=CC=C(Cl)C=C1 YTSDAHZZAZSJJB-UHFFFAOYSA-N 0.000 claims description 2
MKNILBHXNSANDH-UHFFFAOYSA-N [2-amino-4-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]-5-methylthiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C1CN(C=2C=CC(Cl)=CC=2)CCN1CC1=C(C)SC(N)=C1C(=O)C1=CC=C(Cl)C=C1 MKNILBHXNSANDH-UHFFFAOYSA-N 0.000 claims description 2
VQGCSQVHKQRFTI-UHFFFAOYSA-N [2-amino-4-[[4-(4-chlorophenyl)piperidin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCC1C1=CC=C(Cl)C=C1 VQGCSQVHKQRFTI-UHFFFAOYSA-N 0.000 claims description 2
VMLCVTIAPHRDMD-UHFFFAOYSA-N [2-amino-4-[[4-(4-fluorophenyl)piperazin-1-yl]methyl]-5-methylthiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C1CN(C=2C=CC(F)=CC=2)CCN1CC1=C(C)SC(N)=C1C(=O)C1=CC=C(Cl)C=C1 VMLCVTIAPHRDMD-UHFFFAOYSA-N 0.000 claims description 2
ZKWSINKFKJPGQH-UHFFFAOYSA-N [2-amino-4-[[4-(4-iodophenyl)piperazin-1-yl]methyl]-5-methylthiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C1CN(C=2C=CC(I)=CC=2)CCN1CC1=C(C)SC(N)=C1C(=O)C1=CC=C(Cl)C=C1 ZKWSINKFKJPGQH-UHFFFAOYSA-N 0.000 claims description 2
QQBFTEIZJXNNOZ-UHFFFAOYSA-N [2-amino-4-[[4-(4-methylphenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C1=CC(C)=CC=C1N1CCN(CC=2C(=C(N)SC=2)C(=O)C=2C=CC(Cl)=CC=2)CC1 QQBFTEIZJXNNOZ-UHFFFAOYSA-N 0.000 claims description 2
JXLRWJMBKLELNA-UHFFFAOYSA-N [2-amino-4-[[4-(4-nitrophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=C([N+]([O-])=O)C=C1 JXLRWJMBKLELNA-UHFFFAOYSA-N 0.000 claims description 2
QPOPDJJHKWFMOW-UHFFFAOYSA-N [2-amino-4-[[4-[(4-chlorophenyl)methyl]piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1CC1=CC=C(Cl)C=C1 QPOPDJJHKWFMOW-UHFFFAOYSA-N 0.000 claims description 2
DZGCVGMLWHAEKM-UHFFFAOYSA-N [2-amino-4-[[4-[(4-fluorophenyl)methyl]piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1CC1=CC=C(F)C=C1 DZGCVGMLWHAEKM-UHFFFAOYSA-N 0.000 claims description 2
ZGXZMEGSHAZRAK-UHFFFAOYSA-N [2-amino-4-[[4-[2-(4-chlorophenyl)ethyl]piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1CCC1=CC=C(Cl)C=C1 ZGXZMEGSHAZRAK-UHFFFAOYSA-N 0.000 claims description 2
IIEVNVFDTPPXOR-UHFFFAOYSA-N [2-amino-4-[[4-[3-(4-chlorophenyl)propyl]piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1CCCC1=CC=C(Cl)C=C1 IIEVNVFDTPPXOR-UHFFFAOYSA-N 0.000 claims description 2
NIWKJXXHKUGXMO-UHFFFAOYSA-N [2-amino-4-[[4-[3-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=CC(C(F)(F)F)=C1 NIWKJXXHKUGXMO-UHFFFAOYSA-N 0.000 claims description 2
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