MXPA06010520A - Derivados de tiofeno sustituidos como agentes anticancerosos. - Google Patents

Info

Publication number

MXPA06010520A

MXPA06010520A MXPA06010520A MXPA06010520A MXPA06010520A MX PA06010520 A MXPA06010520 A MX PA06010520A MX PA06010520 A MXPA06010520 A MX PA06010520A MX PA06010520 A MXPA06010520 A MX PA06010520A MX PA06010520 A MXPA06010520 A MX PA06010520A

Authority

MX

Mexico

Prior art keywords

carboxamide

thiophene

pyrimidin

methylamino

ethyl

Prior art date

2004-03-30

Links

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• 239000002246 antineoplastic agent Substances 0.000 title claims description 9
• 150000003577 thiophenes Chemical class 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 188
• 239000000203 mixture Substances 0.000 claims abstract description 172
• 150000003839 salts Chemical class 0.000 claims abstract description 16
• 150000002148 esters Chemical class 0.000 claims abstract description 10
• 239000000651 prodrug Substances 0.000 claims abstract description 9
• 229940002612 prodrug Drugs 0.000 claims abstract description 9
• 239000003937 drug carrier Substances 0.000 claims abstract description 6
• -1 carboxyl ester Chemical class 0.000 claims description 494
• 125000000217 alkyl group Chemical group 0.000 claims description 139
• 125000004432 carbon atom Chemical group C* 0.000 claims description 117
• 125000000623 heterocyclic group Chemical group 0.000 claims description 95
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 89
• 125000001072 heteroaryl group Chemical group 0.000 claims description 84
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 76
• 125000003118 aryl group Chemical group 0.000 claims description 59
• 239000001257 hydrogen Substances 0.000 claims description 53
• 229910052739 hydrogen Inorganic materials 0.000 claims description 53
• 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 49
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 48
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 48
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 48
• 238000000034 method Methods 0.000 claims description 47
• 206010028980 Neoplasm Diseases 0.000 claims description 45
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 45
• 102100034744 Cell division cycle 7-related protein kinase Human genes 0.000 claims description 42
• 101000945740 Homo sapiens Cell division cycle 7-related protein kinase Proteins 0.000 claims description 42
• 125000003107 substituted aryl group Chemical group 0.000 claims description 42
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 40
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 39
• 125000001424 substituent group Chemical group 0.000 claims description 38
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 37
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 27
• 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 26
• 125000003342 alkenyl group Chemical group 0.000 claims description 25
• 229910052799 carbon Inorganic materials 0.000 claims description 25
• 201000011510 cancer Diseases 0.000 claims description 24
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims description 23
• 125000003545 alkoxy group Chemical group 0.000 claims description 22
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 20
• 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 19
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 18
• 125000000304 alkynyl group Chemical group 0.000 claims description 17
• 125000004104 aryloxy group Chemical group 0.000 claims description 17
• 229910052757 nitrogen Inorganic materials 0.000 claims description 16
• 125000005843 halogen group Chemical group 0.000 claims description 15
• 125000002947 alkylene group Chemical group 0.000 claims description 14
• 150000001721 carbon Chemical class 0.000 claims description 14
• 230000001404 mediated effect Effects 0.000 claims description 14
• 125000002252 acyl group Chemical group 0.000 claims description 13
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 13
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 13
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 12
• 125000004442 acylamino group Chemical group 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
• 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 10
• 125000004414 alkyl thio group Chemical group 0.000 claims description 10
• 230000002401 inhibitory effect Effects 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
• 238000011282 treatment Methods 0.000 claims description 9
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
• 230000001419 dependent effect Effects 0.000 claims description 8
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 8
• 238000006467 substitution reaction Methods 0.000 claims description 8
• 125000003282 alkyl amino group Chemical group 0.000 claims description 7
• 125000004429 atom Chemical group 0.000 claims description 7
• 125000004433 nitrogen atom Chemical group N* 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
• 229920002554 vinyl polymer Polymers 0.000 claims description 7
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
• 239000004202 carbamide Substances 0.000 claims description 6
• 125000006413 ring segment Chemical group 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 239000011593 sulfur Substances 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
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 5
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 5
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
• 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims description 5
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
• 229910052760 oxygen Inorganic materials 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 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
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
• 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 4
• 150000003573 thiols Chemical class 0.000 claims description 4
• 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
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([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
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 3
• 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
• 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
• 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 3
• 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 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
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 2
• 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
• 125000006288 3,5-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(C([H])=C1F)C([H])([H])* 0.000 claims description 2
• 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 description 2
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[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
• 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[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
• 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 claims description 2
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 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
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
• 241001024304 Mino Species 0.000 claims description 2
• 150000007860 aryl ester derivatives Chemical class 0.000 claims description 2
• 125000000638 benzylaminocarbonyl group Chemical group C(C1=CC=CC=C1)NC(=O)* 0.000 claims description 2
• 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 2
• UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 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
• RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical group C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 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
• 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[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
• 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
• 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
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 8
• WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 3
• 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 2
• 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
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 2
• 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 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
• 125000003070 2-(2-chlorophenyl)ethyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
• OXRMYJAKCWMHED-UHFFFAOYSA-N 3-(1,3-benzothiazol-2-yl)thiophene-2-carboxamide Chemical compound S1C=CC(C=2SC3=CC=CC=C3N=2)=C1C(=O)N OXRMYJAKCWMHED-UHFFFAOYSA-N 0.000 claims 1
• 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 1
• 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 claims 1
• IHXNIOYEXQWUNI-UHFFFAOYSA-N 4,5-dihydro-1h-pyrimidin-6-one Chemical compound O=C1CCN=CN1 IHXNIOYEXQWUNI-UHFFFAOYSA-N 0.000 claims 1
• VOWXAMZJYPLGFZ-UHFFFAOYSA-N 4-(4-methoxyphenyl)-1,3-thiazole Chemical compound C1=CC(OC)=CC=C1C1=CSC=N1 VOWXAMZJYPLGFZ-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
• 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 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
• LVQLXDADAXLOST-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-(1h-benzimidazol-2-ylmethyl)thiophene-2-carboxamide Chemical compound NC1=NC=CC(C=2SC(=CC=2)C(=O)NCC=2NC3=CC=CC=C3N=2)=N1 LVQLXDADAXLOST-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
• 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
• 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-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
• OIPICQKGIKHLLG-UHFFFAOYSA-N 5-(2-aminopyrimidin-4-yl)-n-[1-(4-chlorophenyl)-3-(methylamino)propyl]thiophene-2-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(CCNC)NC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 OIPICQKGIKHLLG-UHFFFAOYSA-N 0.000 claims 1
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• 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
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• 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
• 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
• 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
• 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
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• 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
• 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
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• 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
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• 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
• 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
• 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
• 239000004472 Lysine Substances 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
• 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
• 125000006309 butyl amino group Chemical group 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
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• 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
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• 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 1
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