JP2007531757A - 抗癌剤としての置換チオフェン誘導体 - Google Patents

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Publication number

JP2007531757A

JP2007531757A JP2007506511A JP2007506511A JP2007531757A JP 2007531757 A JP2007531757 A JP 2007531757A JP 2007506511 A JP2007506511 A JP 2007506511A JP 2007506511 A JP2007506511 A JP 2007506511A JP 2007531757 A JP2007531757 A JP 2007531757A

Authority

JP

Japan

Prior art keywords

carboxamide

thiophene

pyrimidin

methylamino

ethyl

Prior art date

2004-03-30

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.)

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• 239000002246 antineoplastic agent Substances 0.000 title claims description 8
• 150000003577 thiophenes Chemical class 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 201
• 239000000203 mixture Substances 0.000 claims abstract description 157
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 45
• 102100034744 Cell division cycle 7-related protein kinase Human genes 0.000 claims abstract description 43
• 101000945740 Homo sapiens Cell division cycle 7-related protein kinase Proteins 0.000 claims abstract description 43
• 201000011510 cancer Diseases 0.000 claims abstract description 30
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
• 150000003839 salts Chemical class 0.000 claims abstract description 17
• 230000001404 mediated effect Effects 0.000 claims abstract description 15
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 14
• 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 13
• 150000002148 esters Chemical class 0.000 claims abstract description 11
• 239000000651 prodrug Substances 0.000 claims abstract description 10
• 229940002612 prodrug Drugs 0.000 claims abstract description 10
• 239000003937 drug carrier Substances 0.000 claims abstract description 7
• -1 carboxyl ester Chemical class 0.000 claims description 588
• 125000000623 heterocyclic group Chemical group 0.000 claims description 93
• 125000001072 heteroaryl group Chemical group 0.000 claims description 81
• 125000000217 alkyl group Chemical group 0.000 claims description 80
• 125000003118 aryl group Chemical group 0.000 claims description 63
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 57
• 239000001257 hydrogen Substances 0.000 claims description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims description 51
• 238000000034 method Methods 0.000 claims description 51
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 45
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 40
• 125000001424 substituent group Chemical group 0.000 claims description 40
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 37
• 125000003107 substituted aryl group Chemical group 0.000 claims description 36
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 34
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 33
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 31
• 125000004432 carbon atom Chemical group C* 0.000 claims description 28
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 27
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 26
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 24
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 22
• 229910052799 carbon Inorganic materials 0.000 claims description 21
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
• 125000004104 aryloxy group Chemical group 0.000 claims description 18
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 14
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 13
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 13
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 12
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 12
• 125000002252 acyl group Chemical group 0.000 claims description 11
• 125000004442 acylamino group Chemical group 0.000 claims description 11
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
• DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims description 11
• 125000004414 alkyl thio group Chemical group 0.000 claims description 10
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 10
• 230000002401 inhibitory effect Effects 0.000 claims description 10
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 10
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 10
• 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims description 9
• 125000002947 alkylene group Chemical group 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 229910052717 sulfur Inorganic materials 0.000 claims description 7
• 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 125000003282 alkyl amino group Chemical group 0.000 claims description 6
• 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 6
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
• 239000004202 carbamide Substances 0.000 claims description 6
• VWEBSWBFMBFVOS-UHFFFAOYSA-N n-[2-(4-fluorophenyl)ethyl]-5-[5-methyl-2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=C(C)C(C=2SC(=CC=2)C(=O)NCCC=2C=CC(F)=CC=2)=N1 VWEBSWBFMBFVOS-UHFFFAOYSA-N 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 6
• 125000006413 ring segment Chemical group 0.000 claims description 6
• 239000011593 sulfur Substances 0.000 claims description 6
• 229920002554 vinyl polymer Polymers 0.000 claims description 6
• 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 5
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 150000003573 thiols Chemical class 0.000 claims description 5
• 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims description 4
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 4
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
• 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims description 3
• YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 claims description 3
• 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 3
• NBSAHLXYOZVQLE-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-sulfonamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)S(=O)(=O)NCCC=2C(=CC(Cl)=CC=2)Cl)=N1 NBSAHLXYOZVQLE-UHFFFAOYSA-N 0.000 claims description 3
• JJYPEEFKRBLOSR-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide Chemical compound S1C(C(=O)N)=CC=C1C1=CC=NC(N)=N1 JJYPEEFKRBLOSR-UHFFFAOYSA-N 0.000 claims description 3
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 3
• 125000003277 amino group Chemical group 0.000 claims description 3
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 3
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 3
• 150000003857 carboxamides Chemical class 0.000 claims description 3
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
• QPYFGRWLGVZTGI-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-sulfonamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)S(=O)(=O)NCCC=2C=CC(Cl)=CC=2)=N1 QPYFGRWLGVZTGI-UHFFFAOYSA-N 0.000 claims description 3
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
• 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims description 2
• 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims description 2
• 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
• 125000002927 2-methoxybenzyl group Chemical group [H]C1=C([H])C([H])=C(C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 2
• 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 2
• 125000006188 2-phenyl benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims description 2
• 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 claims description 2
• XPQRYCUXLRXKMQ-UHFFFAOYSA-N 3-amino-n-[2-(2,4-dichlorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=C(N)C=2)C(=O)NCCC=2C(=CC(Cl)=CC=2)Cl)=N1 XPQRYCUXLRXKMQ-UHFFFAOYSA-N 0.000 claims description 2
• 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 claims description 2
• 125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 2
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
• IHXNIOYEXQWUNI-UHFFFAOYSA-N 4,5-dihydro-1h-pyrimidin-6-one Chemical compound O=C1CCN=CN1 IHXNIOYEXQWUNI-UHFFFAOYSA-N 0.000 claims description 2
• 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 claims description 2
• 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims description 2
• LIGYTORWTOTIQC-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-(2-phenylethyl)thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=CC=CC=2)=N1 LIGYTORWTOTIQC-UHFFFAOYSA-N 0.000 claims description 2
• SSVSNUYEDRPXJR-UHFFFAOYSA-N 6-(2-aminopyrimidin-4-yl)-3-[2-(2,4-dichlorophenyl)ethyl]thieno[3,2-d]pyrimidin-4-one Chemical compound NC1=NC=CC(C=2SC=3C(=O)N(CCC=4C(=CC(Cl)=CC=4)Cl)C=NC=3C=2)=N1 SSVSNUYEDRPXJR-UHFFFAOYSA-N 0.000 claims description 2
• 239000004472 Lysine Substances 0.000 claims description 2
• 125000000638 benzylaminocarbonyl group Chemical group C(C1=CC=CC=C1)NC(=O)* 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000006260 ethylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])C([H])([H])[H] 0.000 claims description 2
• 125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 claims description 2
• 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 2
• 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 2
• 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 2
• UQJIBVBUYFZGLL-UHFFFAOYSA-N n-(4-chloro-1,3-benzothiazol-2-yl)-3-hydroxy-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=C(O)C=2)C(=O)NC=2SC3=CC=CC(Cl)=C3N=2)=N1 UQJIBVBUYFZGLL-UHFFFAOYSA-N 0.000 claims description 2
• AEFXFKAEVKAHGS-UHFFFAOYSA-N n-(4-methoxy-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC=CC(OC)=C3N=2)=N1 AEFXFKAEVKAHGS-UHFFFAOYSA-N 0.000 claims description 2
• HIJOLKIVKMBZSX-HNNXBMFYSA-N n-[(2s)-1-amino-3-(2,4-dichlorophenyl)propan-2-yl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound C([C@@H](CN)NC(=O)C=1SC(=CC=1)C=1C=CN=CC=1)C1=CC=C(Cl)C=C1Cl HIJOLKIVKMBZSX-HNNXBMFYSA-N 0.000 claims description 2
• XURUQPNEBSLOTC-UHFFFAOYSA-N n-[2-(4-fluorophenyl)ethyl]-5-[2-(methylamino)pyridin-4-yl]thiophene-2-carboxamide Chemical compound C1=NC(NC)=CC(C=2SC(=CC=2)C(=O)NCCC=2C=CC(F)=CC=2)=C1 XURUQPNEBSLOTC-UHFFFAOYSA-N 0.000 claims description 2
• VQWCRDHPNXZMIT-UHFFFAOYSA-N n-[2-(4-fluorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=CC(F)=CC=2)=N1 VQWCRDHPNXZMIT-UHFFFAOYSA-N 0.000 claims description 2
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims description 2
• 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 2
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 10
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 7
• 125000001475 halogen functional group Chemical group 0.000 claims 3
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 3
• WEXAVDOGLDFHQL-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(4-methoxy-1,3-benzothiazol-2-yl)thiophene-2-carboxamide Chemical compound N=1C=2C(OC)=CC=CC=2SC=1NC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 WEXAVDOGLDFHQL-UHFFFAOYSA-N 0.000 claims 2
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 2
• HHOVRZGUSBMKKU-ZDUSSCGKSA-N n-[(1s)-2-amino-1-(2,4-dichlorobenzyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)N[C@H](CN)CC=2C(=CC(Cl)=CC=2)Cl)=N1 HHOVRZGUSBMKKU-ZDUSSCGKSA-N 0.000 claims 2
• 125000000980 1H-indol-3-ylmethyl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C(C([H])([H])[*])C2=C1[H] 0.000 claims 1
• MZWHUYLRDIDNRG-UHFFFAOYSA-N 3-(2-aminoethoxy)-n-(4-chloro-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=C(OCCN)C=2)C(=O)NC=2SC3=CC=CC(Cl)=C3N=2)=N1 MZWHUYLRDIDNRG-UHFFFAOYSA-N 0.000 claims 1
• BPRGBSYSQVRXNR-UHFFFAOYSA-N 3-[2-(2,4-dichlorophenyl)ethyl]-6-[2-(methylamino)pyrimidin-4-yl]thieno[3,2-d]pyrimidin-4-one Chemical compound CNC1=NC=CC(C=2SC=3C(=O)N(CCC=4C(=CC(Cl)=CC=4)Cl)C=NC=3C=2)=N1 BPRGBSYSQVRXNR-UHFFFAOYSA-N 0.000 claims 1
• QNVHMIQCVOXFHS-UHFFFAOYSA-N 3-amino-n-(4-chloro-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=C(N)C=2)C(=O)NC=2SC3=CC=CC(Cl)=C3N=2)=N1 QNVHMIQCVOXFHS-UHFFFAOYSA-N 0.000 claims 1
• 125000004042 4-aminobutyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])N([H])[H] 0.000 claims 1
• HWOYVCYUWKJONH-UHFFFAOYSA-N 4-chloro-n-[[5-[2-(methylamino)pyrimidin-4-yl]thiophen-2-yl]methyl]-1,3-benzothiazol-2-amine Chemical compound CNC1=NC=CC(C=2SC(CNC=3SC4=CC=CC(Cl)=C4N=3)=CC=2)=N1 HWOYVCYUWKJONH-UHFFFAOYSA-N 0.000 claims 1
• NPTZTUDTQQZJDC-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(1,3-benzothiazol-2-yl)thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC=CC=C3N=2)=N1 NPTZTUDTQQZJDC-UHFFFAOYSA-N 0.000 claims 1
• FNEVLTPNUHMCJW-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(1h-benzimidazol-2-yl)thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2NC3=CC=CC=C3N=2)=N1 FNEVLTPNUHMCJW-UHFFFAOYSA-N 0.000 claims 1
• PYYUPKMXPCFNBT-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(2-hydroxy-1-phenylethyl)thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC(CO)C=2C=CC=CC=2)=N1 PYYUPKMXPCFNBT-UHFFFAOYSA-N 0.000 claims 1
• XMEWJNGGFIDRIO-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(2-phenylpropyl)thiophene-2-carboxamide Chemical compound C=1C=CC=CC=1C(C)CNC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 XMEWJNGGFIDRIO-UHFFFAOYSA-N 0.000 claims 1
• XNANVNNMNLUYPZ-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(2-pyridin-3-ylethyl)thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=NC=CC=2)=N1 XNANVNNMNLUYPZ-UHFFFAOYSA-N 0.000 claims 1
• CRBQBIVQWYSTAN-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(4,6-dichloro-1,3-benzothiazol-2-yl)thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC(Cl)=CC(Cl)=C3N=2)=N1 CRBQBIVQWYSTAN-UHFFFAOYSA-N 0.000 claims 1
• MTKKCZSXSDQIAQ-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(4,6-difluoro-1,3-benzothiazol-2-yl)thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC(F)=CC(F)=C3N=2)=N1 MTKKCZSXSDQIAQ-UHFFFAOYSA-N 0.000 claims 1
• HUBYTTGYYAONET-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(4-bromo-1,3-benzothiazol-2-yl)thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC=CC(Br)=C3N=2)=N1 HUBYTTGYYAONET-UHFFFAOYSA-N 0.000 claims 1
• XMGDTDAXGWPTSR-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(4-chloro-1,3-benzothiazol-2-yl)thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC=CC(Cl)=C3N=2)=N1 XMGDTDAXGWPTSR-UHFFFAOYSA-N 0.000 claims 1
• JFHNDLNJWMSSJU-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(4-chloro-1,3-benzoxazol-2-yl)thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2OC3=CC=CC(Cl)=C3N=2)=N1 JFHNDLNJWMSSJU-UHFFFAOYSA-N 0.000 claims 1
• QXRYEJPCGMQPGU-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(4-chloro-6-methyl-1,3-benzothiazol-2-yl)thiophene-2-carboxamide Chemical compound S1C2=CC(C)=CC(Cl)=C2N=C1NC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 QXRYEJPCGMQPGU-UHFFFAOYSA-N 0.000 claims 1
• NQNWPDHBHJBOQN-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(4-fluoro-1,3-benzothiazol-2-yl)thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC=CC(F)=C3N=2)=N1 NQNWPDHBHJBOQN-UHFFFAOYSA-N 0.000 claims 1
• AUKWTEYRSILVGT-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(4-hydroxy-1,3-benzothiazol-2-yl)thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC=CC(O)=C3N=2)=N1 AUKWTEYRSILVGT-UHFFFAOYSA-N 0.000 claims 1
• SUJCLYSOQYHCER-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(4-phenyl-1,3-thiazol-2-yl)thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC=C(N=2)C=2C=CC=CC=2)=N1 SUJCLYSOQYHCER-UHFFFAOYSA-N 0.000 claims 1
• UHAYTDSERFCPIU-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(4-pyridin-2-yl-1,3-thiazol-2-yl)thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC=C(N=2)C=2N=CC=CC=2)=N1 UHAYTDSERFCPIU-UHFFFAOYSA-N 0.000 claims 1
• QOKWBHQYKMVXLN-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC=C(N=2)C=2C=NC=CC=2)=N1 QOKWBHQYKMVXLN-UHFFFAOYSA-N 0.000 claims 1
• LAHORGMYKLZDPA-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(5-chloro-1,3-benzothiazol-2-yl)thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC=C(Cl)C=C3N=2)=N1 LAHORGMYKLZDPA-UHFFFAOYSA-N 0.000 claims 1
• KVEMIEMSWHDUIY-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(7-chloro-1,3-benzothiazol-2-yl)thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=C(Cl)C=CC=C3N=2)=N1 KVEMIEMSWHDUIY-UHFFFAOYSA-N 0.000 claims 1
• KGICFSCMVZEXTP-ZDUSSCGKSA-N 5-(2-aminopyrimidin-4-yl)-n-[(2r)-2-(4-chlorophenyl)-2-hydroxyethyl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC[C@H](O)C=2C=CC(Cl)=CC=2)=N1 KGICFSCMVZEXTP-ZDUSSCGKSA-N 0.000 claims 1
• XMEWJNGGFIDRIO-LBPRGKRZSA-N 5-(2-aminopyrimidin-4-yl)-n-[(2r)-2-phenylpropyl]thiophene-2-carboxamide Chemical compound C([C@H](C)C=1C=CC=CC=1)NC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 XMEWJNGGFIDRIO-LBPRGKRZSA-N 0.000 claims 1
• XMEWJNGGFIDRIO-GFCCVEGCSA-N 5-(2-aminopyrimidin-4-yl)-n-[(2s)-2-phenylpropyl]thiophene-2-carboxamide Chemical compound C([C@@H](C)C=1C=CC=CC=1)NC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 XMEWJNGGFIDRIO-GFCCVEGCSA-N 0.000 claims 1
• CFLCOFVWOJTRCB-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[1-(4-chlorophenyl)-3-(dimethylamino)propyl]thiophene-2-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(CCN(C)C)NC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 CFLCOFVWOJTRCB-UHFFFAOYSA-N 0.000 claims 1
• UZJHGGDNLWLNIC-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C(=CC(Cl)=CC=2)Cl)=N1 UZJHGGDNLWLNIC-UHFFFAOYSA-N 0.000 claims 1
• MAXALQSSMNJURH-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[2-(2,4-dichlorophenyl)pent-4-enyl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NCC(CC=C)C=2C(=CC(Cl)=CC=2)Cl)=N1 MAXALQSSMNJURH-UHFFFAOYSA-N 0.000 claims 1
• SPMCOJWMYNBROI-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[2-(2,4-dichlorophenyl)pent-4-ynyl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NCC(CC#C)C=2C(=CC(Cl)=CC=2)Cl)=N1 SPMCOJWMYNBROI-UHFFFAOYSA-N 0.000 claims 1
• YHSMOAXQCDDYTD-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[2-(2,4-dichlorophenyl)pentyl]thiophene-2-carboxamide Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(CCC)CNC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 YHSMOAXQCDDYTD-UHFFFAOYSA-N 0.000 claims 1
• RCIHDNFMDYSGRD-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[2-(2,4-dichlorophenyl)propyl]thiophene-2-carboxamide Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(C)CNC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 RCIHDNFMDYSGRD-UHFFFAOYSA-N 0.000 claims 1
• LPVFDFUNENYSFU-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[2-(2,6-dichlorophenyl)ethyl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C(=CC=CC=2Cl)Cl)=N1 LPVFDFUNENYSFU-UHFFFAOYSA-N 0.000 claims 1
• PEDRXWZBJBNIOW-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[2-(2-chlorophenyl)ethyl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C(=CC=CC=2)Cl)=N1 PEDRXWZBJBNIOW-UHFFFAOYSA-N 0.000 claims 1
• LANAZOCDBPOFPX-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[2-(2-fluoro-4-methoxyphenyl)ethyl]thiophene-2-carboxamide Chemical compound FC1=CC(OC)=CC=C1CCNC(=O)C1=CC=C(C=2N=C(N)N=CC=2)S1 LANAZOCDBPOFPX-UHFFFAOYSA-N 0.000 claims 1
• SQVVLPCNHZIYMB-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[2-(2-fluoro-4-methylphenyl)ethyl]thiophene-2-carboxamide Chemical compound FC1=CC(C)=CC=C1CCNC(=O)C1=CC=C(C=2N=C(N)N=CC=2)S1 SQVVLPCNHZIYMB-UHFFFAOYSA-N 0.000 claims 1
• NUTJLMPCFZERPW-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[2-(3,4-dichlorophenyl)ethyl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=C(Cl)C(Cl)=CC=2)=N1 NUTJLMPCFZERPW-UHFFFAOYSA-N 0.000 claims 1
• AWDIZMAZPSUOPG-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[2-(3-chlorophenyl)ethyl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=C(Cl)C=CC=2)=N1 AWDIZMAZPSUOPG-UHFFFAOYSA-N 0.000 claims 1
• XKBGGFLQRNZRJW-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[2-(4-chlorophenyl)ethyl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=CC(Cl)=CC=2)=N1 XKBGGFLQRNZRJW-UHFFFAOYSA-N 0.000 claims 1
• NTYZKDOMUPHNRB-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[2-(4-fluorophenyl)ethyl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=CC(F)=CC=2)=N1 NTYZKDOMUPHNRB-UHFFFAOYSA-N 0.000 claims 1
• RNADBBOCLFKEFW-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[2-(4-fluorophenyl)ethyl]thiophene-2-sulfonamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)S(=O)(=O)NCCC=2C=CC(F)=CC=2)=N1 RNADBBOCLFKEFW-UHFFFAOYSA-N 0.000 claims 1
• JPEZMMIWJRFRFN-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC=C(N=2)C=2C(=CC=CC=2)Cl)=N1 JPEZMMIWJRFRFN-UHFFFAOYSA-N 0.000 claims 1
• DTDCBIKDTZKDRC-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC=C(N=2)C=2C=C(F)C(F)=CC=2)=N1 DTDCBIKDTZKDRC-UHFFFAOYSA-N 0.000 claims 1
• UWZFVXSUYUSLJH-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[4-(3-chlorophenyl)-1,3-thiazol-2-yl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC=C(N=2)C=2C=C(Cl)C=CC=2)=N1 UWZFVXSUYUSLJH-UHFFFAOYSA-N 0.000 claims 1
• BGFTVXXILCFFDY-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]thiophene-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CSC(NC(=O)C=2SC(=CC=2)C=2N=C(N)N=CC=2)=N1 BGFTVXXILCFFDY-UHFFFAOYSA-N 0.000 claims 1
• FDBIYDXSNVVOKR-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[4-chloro-6-(2-nitroethyl)-1,3-benzothiazol-2-yl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC(CC[N+]([O-])=O)=CC(Cl)=C3N=2)=N1 FDBIYDXSNVVOKR-UHFFFAOYSA-N 0.000 claims 1
• ODNWBUAWVNJCIX-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[4-chloro-6-(hydroxymethyl)-1,3-benzothiazol-2-yl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC(CO)=CC(Cl)=C3N=2)=N1 ODNWBUAWVNJCIX-UHFFFAOYSA-N 0.000 claims 1
• QXDRCBXIBWLXER-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[4-chloro-6-(morpholin-4-ylmethyl)-1,3-benzothiazol-2-yl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC(CN4CCOCC4)=CC(Cl)=C3N=2)=N1 QXDRCBXIBWLXER-UHFFFAOYSA-N 0.000 claims 1
• GKWAVOOYICWTIK-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[4-chloro-6-(trifluoromethoxy)-1,3-benzothiazol-2-yl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC(OC(F)(F)F)=CC(Cl)=C3N=2)=N1 GKWAVOOYICWTIK-UHFFFAOYSA-N 0.000 claims 1
• BXSQEDMSIROAAW-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[4-chloro-6-(trifluoromethyl)-1,3-benzothiazol-2-yl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC(=CC(Cl)=C3N=2)C(F)(F)F)=N1 BXSQEDMSIROAAW-UHFFFAOYSA-N 0.000 claims 1
• VEJCRRQADBUYFT-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[4-chloro-6-[(dimethylamino)methyl]-1,3-benzothiazol-2-yl]thiophene-2-carboxamide Chemical compound S1C2=CC(CN(C)C)=CC(Cl)=C2N=C1NC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 VEJCRRQADBUYFT-UHFFFAOYSA-N 0.000 claims 1
• ACNGIGBNSAVXLG-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[5-(3-bromo-4-methoxyphenyl)-1,3-thiazol-2-yl]thiophene-2-carboxamide Chemical compound C1=C(Br)C(OC)=CC=C1C(S1)=CN=C1NC(=O)C1=CC=C(C=2N=C(N)N=CC=2)S1 ACNGIGBNSAVXLG-UHFFFAOYSA-N 0.000 claims 1
• FDKNPSYDZBINEL-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[[1-(4-chlorophenyl)cyclobutyl]methyl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NCC2(CCC2)C=2C=CC(Cl)=CC=2)=N1 FDKNPSYDZBINEL-UHFFFAOYSA-N 0.000 claims 1
• CMRWNLCSJWAETG-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[[1-(4-chlorophenyl)cyclopropyl]methyl]thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NCC2(CC2)C=2C=CC(Cl)=CC=2)=N1 CMRWNLCSJWAETG-UHFFFAOYSA-N 0.000 claims 1
• NVNZUMSKDWXVBS-UHFFFAOYSA-N 5-(2-anilinopyrimidin-4-yl)-n-[2-(4-fluorophenyl)ethyl]thiophene-2-carboxamide Chemical compound C1=CC(F)=CC=C1CCNC(=O)C1=CC=C(C=2N=C(NC=3C=CC=CC=3)N=CC=2)S1 NVNZUMSKDWXVBS-UHFFFAOYSA-N 0.000 claims 1
• UAXGDOWTVZTQBY-UHFFFAOYSA-N 5-[2-(benzylamino)pyrimidin-4-yl]-n-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1CCNC(=O)C1=CC=C(C=2N=C(NCC=3C=CC=CC=3)N=CC=2)S1 UAXGDOWTVZTQBY-UHFFFAOYSA-N 0.000 claims 1
• FMXKEISBOAKKPN-UHFFFAOYSA-N 5-[2-(butylamino)pyrimidin-4-yl]-n-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide Chemical compound CCCCNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C(=CC(Cl)=CC=2)Cl)=N1 FMXKEISBOAKKPN-UHFFFAOYSA-N 0.000 claims 1
• FYBVWFQTQKULGT-UHFFFAOYSA-N 5-[2-(cyclobutylamino)pyrimidin-4-yl]-n-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1CCNC(=O)C1=CC=C(C=2N=C(NC3CCC3)N=CC=2)S1 FYBVWFQTQKULGT-UHFFFAOYSA-N 0.000 claims 1
• WQULOHAJMAQTLC-UHFFFAOYSA-N 5-[2-(cyclopentylamino)pyrimidin-4-yl]-n-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1CCNC(=O)C1=CC=C(C=2N=C(NC3CCCC3)N=CC=2)S1 WQULOHAJMAQTLC-UHFFFAOYSA-N 0.000 claims 1
• XWBHEAVRYIOCDA-UHFFFAOYSA-N 5-[2-(cyclopropylamino)pyrimidin-4-yl]-n-[2-(2,4-dichlorophenyl)ethyl]thiophene-2-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1CCNC(=O)C1=CC=C(C=2N=C(NC3CC3)N=CC=2)S1 XWBHEAVRYIOCDA-UHFFFAOYSA-N 0.000 claims 1
• AGZCRDGUZJDKNH-UHFFFAOYSA-N 5-[2-(dimethylamino)pyrimidin-4-yl]-n-[2-(4-fluorophenyl)ethyl]thiophene-2-carboxamide Chemical compound CN(C)C1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=CC(F)=CC=2)=N1 AGZCRDGUZJDKNH-UHFFFAOYSA-N 0.000 claims 1
• RDSOQXDTFGIAGL-UHFFFAOYSA-N 5-[2-(ethylamino)pyrimidin-4-yl]-n-[2-(4-fluorophenyl)ethyl]thiophene-2-carboxamide Chemical compound CCNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=CC(F)=CC=2)=N1 RDSOQXDTFGIAGL-UHFFFAOYSA-N 0.000 claims 1
• YAQZTVOEXWBHGW-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-(1,2,3,4-tetrahydronaphthalen-1-yl)thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC2C3=CC=CC=C3CCC2)=N1 YAQZTVOEXWBHGW-UHFFFAOYSA-N 0.000 claims 1
• MLCRRFSSEJCWKM-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-(2-morpholin-4-yl-2-phenylethyl)thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCC(N2CCOCC2)C=2C=CC=CC=2)=N1 MLCRRFSSEJCWKM-UHFFFAOYSA-N 0.000 claims 1
• YVWCLQZBYNEBCS-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-(2-morpholin-4-ylethyl)thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCN2CCOCC2)=N1 YVWCLQZBYNEBCS-UHFFFAOYSA-N 0.000 claims 1
• FSBMMNCTVJSKAQ-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-(2-phenylpropyl)thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCC(C)C=2C=CC=CC=2)=N1 FSBMMNCTVJSKAQ-UHFFFAOYSA-N 0.000 claims 1
• INKVUIMEZCZJDU-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-(2-piperidin-1-ylethyl)thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCN2CCCCC2)=N1 INKVUIMEZCZJDU-UHFFFAOYSA-N 0.000 claims 1
• ANCMTSBLWZPSQD-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-(2-pyridin-2-ylethyl)thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2N=CC=CC=2)=N1 ANCMTSBLWZPSQD-UHFFFAOYSA-N 0.000 claims 1
• MZGSYIGYCQFSKV-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-(2-pyridin-4-ylethyl)thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=CN=CC=2)=N1 MZGSYIGYCQFSKV-UHFFFAOYSA-N 0.000 claims 1
• AUJSQMWSRIQLKJ-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-(4-methyl-1,3-benzothiazol-2-yl)thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC=CC(C)=C3N=2)=N1 AUJSQMWSRIQLKJ-UHFFFAOYSA-N 0.000 claims 1
• FMHNLORGXCTUBC-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-(4-phenyl-1,3-thiazol-2-yl)thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC=C(N=2)C=2C=CC=CC=2)=N1 FMHNLORGXCTUBC-UHFFFAOYSA-N 0.000 claims 1
• ILOADZQIXIGSNS-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-(4-pyridin-2-yl-1,3-thiazol-2-yl)thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC=C(N=2)C=2N=CC=CC=2)=N1 ILOADZQIXIGSNS-UHFFFAOYSA-N 0.000 claims 1
• BMSMVHRXCQBORR-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC=C(N=2)C=2C=NC=CC=2)=N1 BMSMVHRXCQBORR-UHFFFAOYSA-N 0.000 claims 1
• OFXUEAVLIYUDNI-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-(pyridin-2-ylmethyl)thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCC=2N=CC=CC=2)=N1 OFXUEAVLIYUDNI-UHFFFAOYSA-N 0.000 claims 1
• VGWYYDFAUBZGTJ-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-(pyridin-3-ylmethyl)thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCC=2C=NC=CC=2)=N1 VGWYYDFAUBZGTJ-UHFFFAOYSA-N 0.000 claims 1
• LXVDFAWPGBSWCR-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-(pyridin-4-ylmethyl)thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCC=2C=CN=CC=2)=N1 LXVDFAWPGBSWCR-UHFFFAOYSA-N 0.000 claims 1
• FSBMMNCTVJSKAQ-ZDUSSCGKSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-[(2r)-2-phenylpropyl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC[C@H](C)C=2C=CC=CC=2)=N1 FSBMMNCTVJSKAQ-ZDUSSCGKSA-N 0.000 claims 1
• FSBMMNCTVJSKAQ-CYBMUJFWSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-[(2s)-2-phenylpropyl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC[C@@H](C)C=2C=CC=CC=2)=N1 FSBMMNCTVJSKAQ-CYBMUJFWSA-N 0.000 claims 1
• KWWNNIKIVXQIJU-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-[2-(4-methylphenyl)ethyl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=CC(C)=CC=2)=N1 KWWNNIKIVXQIJU-UHFFFAOYSA-N 0.000 claims 1
• AOYOYTUZOHDUMY-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-[2-(4-methylpiperazin-1-yl)ethyl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCN2CCN(C)CC2)=N1 AOYOYTUZOHDUMY-UHFFFAOYSA-N 0.000 claims 1
• AOCZJDPDLIJLCR-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-[2-(4-phenoxyphenyl)ethyl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=CC(OC=3C=CC=CC=3)=CC=2)=N1 AOCZJDPDLIJLCR-UHFFFAOYSA-N 0.000 claims 1
• SQLQMQPHQGTPHS-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-piperidin-3-ylthiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC2CNCCC2)=N1 SQLQMQPHQGTPHS-UHFFFAOYSA-N 0.000 claims 1
• BFVNGLYYIBSCFZ-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-pyrrolidin-3-ylthiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC2CNCC2)=N1 BFVNGLYYIBSCFZ-UHFFFAOYSA-N 0.000 claims 1
• AKFSTAXJYQVCLG-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-quinolin-2-ylthiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2N=C3C=CC=CC3=CC=2)=N1 AKFSTAXJYQVCLG-UHFFFAOYSA-N 0.000 claims 1
• WSVGIONTZPMOKG-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-quinolin-3-ylthiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2C=C3C=CC=CC3=NC=2)=N1 WSVGIONTZPMOKG-UHFFFAOYSA-N 0.000 claims 1
• FQUGBOHRQSPEBF-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]-n-quinolin-6-ylthiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2C=C3C=CC=NC3=CC=2)=N1 FQUGBOHRQSPEBF-UHFFFAOYSA-N 0.000 claims 1
• XZWFFMMANAOYPA-UHFFFAOYSA-N 5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(N)=O)=N1 XZWFFMMANAOYPA-UHFFFAOYSA-N 0.000 claims 1
• AVRWEULSKHQETA-UHFFFAOYSA-N Thiophene-2 Chemical compound S1C=2CCCCCC=2C(C(=O)OC)=C1NC(=O)C1=C(F)C(F)=C(F)C(F)=C1F AVRWEULSKHQETA-UHFFFAOYSA-N 0.000 claims 1
• 125000003705 anilinocarbonyl group Chemical group O=C([*])N([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims 1
• RTPVYTSJFKBAOC-UHFFFAOYSA-N methyl 2-[[5-(2-aminopyrimidin-4-yl)thiophene-2-carbonyl]amino]-4-chloro-1,3-benzothiazole-5-carboxylate Chemical compound N=1C2=C(Cl)C(C(=O)OC)=CC=C2SC=1NC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 RTPVYTSJFKBAOC-UHFFFAOYSA-N 0.000 claims 1
• YOGAYYYZPISLTN-UHFFFAOYSA-N methyl 4-chloro-2-[[5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carbonyl]amino]-1,3-benzothiazole-5-carboxylate Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC=C(C(Cl)=C3N=2)C(=O)OC)=N1 YOGAYYYZPISLTN-UHFFFAOYSA-N 0.000 claims 1
• GFUONLMQSGRDEX-UHFFFAOYSA-N n-(1,2-diphenylethyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC(CC=2C=CC=CC=2)C=2C=CC=CC=2)=N1 GFUONLMQSGRDEX-UHFFFAOYSA-N 0.000 claims 1
• UVIDDQVRCBLANS-UHFFFAOYSA-N n-(1-benzylpyrrolidin-3-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC2CN(CC=3C=CC=CC=3)CC2)=N1 UVIDDQVRCBLANS-UHFFFAOYSA-N 0.000 claims 1
• NJHYYLPVLKEBQP-UHFFFAOYSA-N n-(2,2-diphenylethyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCC(C=2C=CC=CC=2)C=2C=CC=CC=2)=N1 NJHYYLPVLKEBQP-UHFFFAOYSA-N 0.000 claims 1
• GTZNGZIDDWCVEG-UHFFFAOYSA-N n-(2-aminoethyl)-4-chloro-2-[[5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carbonyl]amino]-1,3-benzothiazole-6-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC(=CC(Cl)=C3N=2)C(=O)NCCN)=N1 GTZNGZIDDWCVEG-UHFFFAOYSA-N 0.000 claims 1
• BMCNSGBPGWNGAW-UHFFFAOYSA-N n-(2-aminoethyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCN)=N1 BMCNSGBPGWNGAW-UHFFFAOYSA-N 0.000 claims 1
• YQIFHDIODVEVBD-UHFFFAOYSA-N n-(2-aminoethyl)-n-(4-chloro-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)N(CCN)C=2SC3=CC=CC(Cl)=C3N=2)=N1 YQIFHDIODVEVBD-UHFFFAOYSA-N 0.000 claims 1
• FYRLHDAYSIJVQN-UHFFFAOYSA-N n-(4,6-difluoro-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC(F)=CC(F)=C3N=2)=N1 FYRLHDAYSIJVQN-UHFFFAOYSA-N 0.000 claims 1
• VOMRJFKDDQGCSZ-UHFFFAOYSA-N n-(4-chloro-1,3-benzothiazol-2-yl)-3-methoxy-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=C(OC)C=2)C(=O)NC=2SC3=CC=CC(Cl)=C3N=2)=N1 VOMRJFKDDQGCSZ-UHFFFAOYSA-N 0.000 claims 1
• UBXMUHDEMWWYEP-UHFFFAOYSA-N n-(4-chloro-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC=CC(Cl)=C3N=2)=N1 UBXMUHDEMWWYEP-UHFFFAOYSA-N 0.000 claims 1
• TYBUDXLJBAFHPA-UHFFFAOYSA-N n-(4-chloro-1,3-benzothiazol-2-yl)-n-methyl-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)N(C)C=2SC3=CC=CC(Cl)=C3N=2)=N1 TYBUDXLJBAFHPA-UHFFFAOYSA-N 0.000 claims 1
• IOVATEWBWZGHIZ-UHFFFAOYSA-N n-(4-chloro-1,3-benzoxazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2OC3=CC=CC(Cl)=C3N=2)=N1 IOVATEWBWZGHIZ-UHFFFAOYSA-N 0.000 claims 1
• SLSKJTKRUUWBKY-UHFFFAOYSA-N n-(4-chloro-6-methyl-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC(C)=CC(Cl)=C3N=2)=N1 SLSKJTKRUUWBKY-UHFFFAOYSA-N 0.000 claims 1
• SLGMKFVHOSMRMA-UHFFFAOYSA-N n-(4-fluorophenyl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2C=CC(F)=CC=2)=N1 SLGMKFVHOSMRMA-UHFFFAOYSA-N 0.000 claims 1
• JTCNQIBIJBDQCP-UHFFFAOYSA-N n-(4-hydroxy-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC=CC(O)=C3N=2)=N1 JTCNQIBIJBDQCP-UHFFFAOYSA-N 0.000 claims 1
• UNQPSFNJYHZYEX-UHFFFAOYSA-N n-(5-chloro-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC=C(Cl)C=C3N=2)=N1 UNQPSFNJYHZYEX-UHFFFAOYSA-N 0.000 claims 1
• QVKDBDYFPRZLLB-UHFFFAOYSA-N n-(6-fluoro-1,3-benzothiazol-2-yl)-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC3=CC(F)=CC=C3N=2)=N1 QVKDBDYFPRZLLB-UHFFFAOYSA-N 0.000 claims 1
• TVBATRHELCPWFC-XPCCGILXSA-N n-[(2r)-2-hydroxy-2,3-dihydro-1h-inden-1-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC2C3=CC=CC=C3C[C@H]2O)=N1 TVBATRHELCPWFC-XPCCGILXSA-N 0.000 claims 1
• SLIFUDFEWWHQQI-GFCCVEGCSA-N n-[(2s)-2-amino-2-phenylethyl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide Chemical compound C([C@@H](N)C=1C=CC=CC=1)NC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 SLIFUDFEWWHQQI-GFCCVEGCSA-N 0.000 claims 1
• XPMIPHQPUWQWIB-CYBMUJFWSA-N n-[(2s)-2-amino-2-phenylethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC[C@@H](N)C=2C=CC=CC=2)=N1 XPMIPHQPUWQWIB-CYBMUJFWSA-N 0.000 claims 1
• SFSMICBLCBGDLK-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCC=2C=CC(F)=CC=2)=N1 SFSMICBLCBGDLK-UHFFFAOYSA-N 0.000 claims 1
• UOLYTRAUGYBDOZ-UHFFFAOYSA-N n-[1-(4-chlorophenyl)-3-(dimethylamino)propyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC(CCN(C)C)C=2C=CC(Cl)=CC=2)=N1 UOLYTRAUGYBDOZ-UHFFFAOYSA-N 0.000 claims 1
• HTKHGJMBTREOOL-UHFFFAOYSA-N n-[1-(4-chlorophenyl)-3-hydroxypropyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC(CCO)C=2C=CC(Cl)=CC=2)=N1 HTKHGJMBTREOOL-UHFFFAOYSA-N 0.000 claims 1
• YZNHMSYFPSNFCI-UHFFFAOYSA-N n-[1-(4-fluorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC(C)C=2C=CC(F)=CC=2)=N1 YZNHMSYFPSNFCI-UHFFFAOYSA-N 0.000 claims 1
• MXMKADGJEUXBFS-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)ethyl]-5-[2-(dimethylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CN(C)C1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C(=CC(Cl)=CC=2)Cl)=N1 MXMKADGJEUXBFS-UHFFFAOYSA-N 0.000 claims 1
• VFIZNSNMLQIIMY-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)ethyl]-5-[2-(ethylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CCNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C(=CC(Cl)=CC=2)Cl)=N1 VFIZNSNMLQIIMY-UHFFFAOYSA-N 0.000 claims 1
• SMYXXLZMXSZYRT-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)ethyl]-5-[2-(methylamino)pyridin-4-yl]thiophene-2-carboxamide Chemical compound C1=NC(NC)=CC(C=2SC(=CC=2)C(=O)NCCC=2C(=CC(Cl)=CC=2)Cl)=C1 SMYXXLZMXSZYRT-UHFFFAOYSA-N 0.000 claims 1
• MPABKDRFTWVLMC-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C(=CC(Cl)=CC=2)Cl)=N1 MPABKDRFTWVLMC-UHFFFAOYSA-N 0.000 claims 1
• ZMPQDHMDRQYSKY-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-sulfonamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)S(=O)(=O)NCCC=2C(=CC(Cl)=CC=2)Cl)=N1 ZMPQDHMDRQYSKY-UHFFFAOYSA-N 0.000 claims 1
• HYOWGDCBCIXWAP-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)ethyl]-5-[2-(propylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CCCNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C(=CC(Cl)=CC=2)Cl)=N1 HYOWGDCBCIXWAP-UHFFFAOYSA-N 0.000 claims 1
• DYESAQIRADGESU-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)ethyl]-5-[2-(pyridin-4-ylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1CCNC(=O)C1=CC=C(C=2N=C(NC=3C=CN=CC=3)N=CC=2)S1 DYESAQIRADGESU-UHFFFAOYSA-N 0.000 claims 1
• MMQXDJGZVCZRSJ-YDNXMHBPSA-N n-[2-(2,4-dichlorophenyl)ethyl]-5-[2-[[(2s)-2-phenylcyclopropyl]amino]pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1CCNC(=O)C1=CC=C(C=2N=C(NC3[C@@H](C3)C=3C=CC=CC=3)N=CC=2)S1 MMQXDJGZVCZRSJ-YDNXMHBPSA-N 0.000 claims 1
• VLICBHXEYNKDHC-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)ethyl]-5-[4-(methylamino)-1,3,5-triazin-2-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=NC(C=2SC(=CC=2)C(=O)NCCC=2C(=CC(Cl)=CC=2)Cl)=N1 VLICBHXEYNKDHC-UHFFFAOYSA-N 0.000 claims 1
• PYVYBANUWNFBKC-UHFFFAOYSA-N n-[2-(2,4-dichlorophenyl)ethyl]-5-pyrimidin-4-ylthiophene-2-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1CCNC(=O)C1=CC=C(C=2N=CN=CC=2)S1 PYVYBANUWNFBKC-UHFFFAOYSA-N 0.000 claims 1
• LVGSFJIMINBHKE-UHFFFAOYSA-N n-[2-(2,5-dimethoxyphenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C(=CC=C(OC)C=2)OC)=N1 LVGSFJIMINBHKE-UHFFFAOYSA-N 0.000 claims 1
• QMGOSDFBFDADFB-UHFFFAOYSA-N n-[2-(2,6-dichlorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C(=CC=CC=2Cl)Cl)=N1 QMGOSDFBFDADFB-UHFFFAOYSA-N 0.000 claims 1
• UCRVNWSQOAMWMH-UHFFFAOYSA-N n-[2-(2-chlorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C(=CC=CC=2)Cl)=N1 UCRVNWSQOAMWMH-UHFFFAOYSA-N 0.000 claims 1
• FHDAWHASPNWEPU-UHFFFAOYSA-N n-[2-(2-fluorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C(=CC=CC=2)F)=N1 FHDAWHASPNWEPU-UHFFFAOYSA-N 0.000 claims 1
• CTHWZLWFDWJTKZ-UHFFFAOYSA-N n-[2-(2-methoxyphenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C(=CC=CC=2)OC)=N1 CTHWZLWFDWJTKZ-UHFFFAOYSA-N 0.000 claims 1
• QLGHBSUHBXDGLW-UHFFFAOYSA-N n-[2-(3,4-dichlorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=C(Cl)C(Cl)=CC=2)=N1 QLGHBSUHBXDGLW-UHFFFAOYSA-N 0.000 claims 1
• URWRQQWYHAMDAH-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=C(OC)C(OC)=CC=2)=N1 URWRQQWYHAMDAH-UHFFFAOYSA-N 0.000 claims 1
• YRCTVYMPNWIFAJ-UHFFFAOYSA-N n-[2-(3-chlorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=C(Cl)C=CC=2)=N1 YRCTVYMPNWIFAJ-UHFFFAOYSA-N 0.000 claims 1
• ICKXYJSTJUCBBZ-UHFFFAOYSA-N n-[2-(3-fluorophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=C(F)C=CC=2)=N1 ICKXYJSTJUCBBZ-UHFFFAOYSA-N 0.000 claims 1
• PVEICDOYZVUTLN-UHFFFAOYSA-N n-[2-(3-methoxyphenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=C(OC)C=CC=2)=N1 PVEICDOYZVUTLN-UHFFFAOYSA-N 0.000 claims 1
• AFSOOPRQPFBEOM-UHFFFAOYSA-N n-[2-(4-aminophenyl)ethyl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide Chemical compound C1=CC(N)=CC=C1CCNC(=O)C1=CC=C(C=2N=C(N)N=CC=2)S1 AFSOOPRQPFBEOM-UHFFFAOYSA-N 0.000 claims 1
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