JP2007531757A5 - - Google Patents
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- Publication number
- JP2007531757A5 JP2007531757A5 JP2007506511A JP2007506511A JP2007531757A5 JP 2007531757 A5 JP2007531757 A5 JP 2007531757A5 JP 2007506511 A JP2007506511 A JP 2007506511A JP 2007506511 A JP2007506511 A JP 2007506511A JP 2007531757 A5 JP2007531757 A5 JP 2007531757A5
- Authority
- JP
- Japan
- Prior art keywords
- carboxamide
- thiophene
- pyrimidin
- methylamino
- ethyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- -1 carboxyl ester Chemical class 0.000 claims 296
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 47
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 29
- 150000001875 compounds Chemical class 0.000 claims 28
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 26
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 22
- 125000000623 heterocyclic group Chemical group 0.000 claims 22
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 18
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 17
- 125000001072 heteroaryl group Chemical group 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 16
- 239000001257 hydrogen Substances 0.000 claims 16
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 12
- 150000002431 hydrogen Chemical class 0.000 claims 10
- 239000000203 mixture Substances 0.000 claims 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 10
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 9
- 125000000547 substituted alkyl group Chemical group 0.000 claims 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 7
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000003107 substituted aryl group Chemical group 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 5
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 4
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 230000001404 mediated effect Effects 0.000 claims 4
- 102100034744 Cell division cycle 7-related protein kinase Human genes 0.000 claims 3
- 101000945740 Homo sapiens Cell division cycle 7-related protein kinase Proteins 0.000 claims 3
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 230000002401 inhibitory effect Effects 0.000 claims 3
- 125000000449 nitro group Chemical class [O-][N+](*)=O 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims 3
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims 2
- 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims 2
- YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 claims 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=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
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000004442 acylamino group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000004104 aryloxy group Chemical group 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
- 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 2
- 239000004202 carbamide Substances 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000005553 heteroaryloxy group Chemical group 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
- 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 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000006514 pyridin-2-ylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims 2
- 125000006413 ring segment Chemical group 0.000 claims 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims 1
- 125000006730 (C2-C5) alkynyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 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
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([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
- 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
- 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 1
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([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
- 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
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([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
- 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 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
- 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
- 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 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
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- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 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 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
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 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
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 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
- 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 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
- 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
- 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
- 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 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
- GMHIHHJFPKGLTE-UHFFFAOYSA-N n-[2-(4-bromophenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=CC(Br)=CC=2)=N1 GMHIHHJFPKGLTE-UHFFFAOYSA-N 0.000 claims 1
- SNEBFCVAIRGLGQ-UHFFFAOYSA-N n-[2-(4-chlorophenyl)-4-hydroxybutyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCC(CCO)C=2C=CC(Cl)=CC=2)=N1 SNEBFCVAIRGLGQ-UHFFFAOYSA-N 0.000 claims 1
- YPNATZHZOCDUHJ-UHFFFAOYSA-N n-[2-(4-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(Cl)=CC=2)=N1 YPNATZHZOCDUHJ-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- GGRVIJWDDOHCBW-UHFFFAOYSA-N n-[2-(4-ethoxyphenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound C1=CC(OCC)=CC=C1CCNC(=O)C1=CC=C(C=2N=C(NC)N=CC=2)S1 GGRVIJWDDOHCBW-UHFFFAOYSA-N 0.000 claims 1
- ZFQUVFPIYPYCSV-UHFFFAOYSA-N n-[2-(4-ethylphenyl)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound C1=CC(CC)=CC=C1CCNC(=O)C1=CC=C(C=2N=C(NC)N=CC=2)S1 ZFQUVFPIYPYCSV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- JXRYCYBMVNQOMQ-UHFFFAOYSA-N n-[2-(4-fluorophenyl)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(F)=CC=2)=N1 JXRYCYBMVNQOMQ-UHFFFAOYSA-N 0.000 claims 1
- FATJKXOPTHBIOJ-UHFFFAOYSA-N n-[2-(4-fluorophenyl)ethyl]-5-[6-(methylamino)pyridin-2-yl]thiophene-2-carboxamide Chemical compound CNC1=CC=CC(C=2SC(=CC=2)C(=O)NCCC=2C=CC(F)=CC=2)=N1 FATJKXOPTHBIOJ-UHFFFAOYSA-N 0.000 claims 1
- AAWNVQYZVTTYED-UHFFFAOYSA-N n-[2-(4-fluorophenyl)ethyl]-5-pyridin-4-ylthiophene-2-carboxamide Chemical compound C1=CC(F)=CC=C1CCNC(=O)C1=CC=C(C=2C=CN=CC=2)S1 AAWNVQYZVTTYED-UHFFFAOYSA-N 0.000 claims 1
- RJVLYJURXGSMMB-UHFFFAOYSA-N n-[2-(4-fluorophenyl)ethyl]-n-methyl-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)N(C)CCC=2C=CC(F)=CC=2)=N1 RJVLYJURXGSMMB-UHFFFAOYSA-N 0.000 claims 1
- ZZYCUCRSTVKYIG-UHFFFAOYSA-N n-[2-(4-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(OC)=CC=2)=N1 ZZYCUCRSTVKYIG-UHFFFAOYSA-N 0.000 claims 1
- NMHPRSZNSIRZJD-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCN(C)C)=N1 NMHPRSZNSIRZJD-UHFFFAOYSA-N 0.000 claims 1
- ATXIGCMNGRDMPV-UHFFFAOYSA-N n-[3-(4-fluorophenyl)propyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCCCC=2C=CC(F)=CC=2)=N1 ATXIGCMNGRDMPV-UHFFFAOYSA-N 0.000 claims 1
- HKAXPJOLHAZMSO-UHFFFAOYSA-N n-[3-amino-1-(4-chlorophenyl)propyl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide Chemical compound C=1C=C(Cl)C=CC=1C(CCN)NC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 HKAXPJOLHAZMSO-UHFFFAOYSA-N 0.000 claims 1
- WMQIUPWPTGHQKW-UHFFFAOYSA-N n-[4-(2-chlorophenyl)-1,3-thiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-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)Cl)=N1 WMQIUPWPTGHQKW-UHFFFAOYSA-N 0.000 claims 1
- NDHYWODVGZGNOR-UHFFFAOYSA-N n-[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC=C(N=2)C=2C=C(F)C(F)=CC=2)=N1 NDHYWODVGZGNOR-UHFFFAOYSA-N 0.000 claims 1
- HGCNQYOKNWGTKD-UHFFFAOYSA-N n-[4-(3-chlorophenyl)-1,3-thiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC=C(N=2)C=2C=C(Cl)C=CC=2)=N1 HGCNQYOKNWGTKD-UHFFFAOYSA-N 0.000 claims 1
- RAKLDOKJEVXJIG-UHFFFAOYSA-N n-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC=C(N=2)C=2C=CC(OC)=CC=2)=N1 RAKLDOKJEVXJIG-UHFFFAOYSA-N 0.000 claims 1
- YKNUPOUJWCCICK-UHFFFAOYSA-N n-[4-(aminomethyl)-1,3-benzothiazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide Chemical compound N=1C=2C(CN)=CC=CC=2SC=1NC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 YKNUPOUJWCCICK-UHFFFAOYSA-N 0.000 claims 1
- OVEZBCVYUORCFG-UHFFFAOYSA-N n-[4-(aminomethyl)-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(CN)=C3N=2)=N1 OVEZBCVYUORCFG-UHFFFAOYSA-N 0.000 claims 1
- SXVBGQYMFWTIMA-UHFFFAOYSA-N n-[4-amino-2-(4-chlorophenyl)butyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCC(CCN)C=2C=CC(Cl)=CC=2)=N1 SXVBGQYMFWTIMA-UHFFFAOYSA-N 0.000 claims 1
- OFKNVJOYELBTFQ-UHFFFAOYSA-N n-[4-chloro-6-(2-nitroethyl)-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[N+]([O-])=O)=CC(Cl)=C3N=2)=N1 OFKNVJOYELBTFQ-UHFFFAOYSA-N 0.000 claims 1
- GUCFIBZUUWTNOO-UHFFFAOYSA-N n-[4-chloro-6-(morpholin-4-ylmethyl)-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(CN4CCOCC4)=CC(Cl)=C3N=2)=N1 GUCFIBZUUWTNOO-UHFFFAOYSA-N 0.000 claims 1
- ASZFEJKKBAQPRU-UHFFFAOYSA-N n-[4-chloro-6-(trifluoromethoxy)-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(OC(F)(F)F)=CC(Cl)=C3N=2)=N1 ASZFEJKKBAQPRU-UHFFFAOYSA-N 0.000 claims 1
- CLKUZOMGQGYILX-UHFFFAOYSA-N n-[4-chloro-6-(trifluoromethyl)-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)C(F)(F)F)=N1 CLKUZOMGQGYILX-UHFFFAOYSA-N 0.000 claims 1
- XRNOLADMONHKAM-UHFFFAOYSA-N n-[4-chloro-6-[(dimethylamino)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(CN(C)C)=CC(Cl)=C3N=2)=N1 XRNOLADMONHKAM-UHFFFAOYSA-N 0.000 claims 1
- VYDHJJKKXAJQAO-UHFFFAOYSA-N n-[4-chloro-7-(hydroxymethyl)-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=C(CO)C=CC(Cl)=C3N=2)=N1 VYDHJJKKXAJQAO-UHFFFAOYSA-N 0.000 claims 1
- KGZPOPXFJLNAKS-UHFFFAOYSA-N n-[5-(3-bromo-4-methoxyphenyl)-1,3-thiazol-2-yl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NC=2SC(=CN=2)C=2C=C(Br)C(OC)=CC=2)=N1 KGZPOPXFJLNAKS-UHFFFAOYSA-N 0.000 claims 1
- QZSOJEQIMXJRLS-UHFFFAOYSA-N n-[6-(2-aminoethyl)-4-chloro-1,3-benzothiazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide Chemical compound S1C2=CC(CCN)=CC(Cl)=C2N=C1NC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 QZSOJEQIMXJRLS-UHFFFAOYSA-N 0.000 claims 1
- WIECFCHPCPFVDC-UHFFFAOYSA-N n-[6-(2-aminoethyl)-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(CCN)=CC(Cl)=C3N=2)=N1 WIECFCHPCPFVDC-UHFFFAOYSA-N 0.000 claims 1
- AOBXWRCCZHGOJW-UHFFFAOYSA-N n-[6-(aminomethyl)-1,3-benzothiazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide Chemical compound S1C2=CC(CN)=CC=C2N=C1NC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 AOBXWRCCZHGOJW-UHFFFAOYSA-N 0.000 claims 1
- LMKQBFNXPKGPAO-UHFFFAOYSA-N n-[6-(aminomethyl)-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(CN)=CC=C3N=2)=N1 LMKQBFNXPKGPAO-UHFFFAOYSA-N 0.000 claims 1
- KAUVTOXYGIWIGL-UHFFFAOYSA-N n-[6-(aminomethyl)-4-(trifluoromethoxy)-1,3-benzothiazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide Chemical compound S1C2=CC(CN)=CC(OC(F)(F)F)=C2N=C1NC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 KAUVTOXYGIWIGL-UHFFFAOYSA-N 0.000 claims 1
- DJYKMVNRPVTKEK-UHFFFAOYSA-N n-[6-(aminomethyl)-4-(trifluoromethoxy)-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(CN)=CC(OC(F)(F)F)=C3N=2)=N1 DJYKMVNRPVTKEK-UHFFFAOYSA-N 0.000 claims 1
- FCHSTIRKQIBTHF-UHFFFAOYSA-N n-[6-(aminomethyl)-4-(trifluoromethyl)-1,3-benzothiazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide Chemical compound S1C2=CC(CN)=CC(C(F)(F)F)=C2N=C1NC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 FCHSTIRKQIBTHF-UHFFFAOYSA-N 0.000 claims 1
- FPQORDSVXQXJLB-UHFFFAOYSA-N n-[6-(aminomethyl)-4-(trifluoromethyl)-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(CN)=CC(=C3N=2)C(F)(F)F)=N1 FPQORDSVXQXJLB-UHFFFAOYSA-N 0.000 claims 1
- YMXTUQYXYGVDSZ-UHFFFAOYSA-N n-[6-(aminomethyl)-4-bromo-1,3-benzothiazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide Chemical compound S1C2=CC(CN)=CC(Br)=C2N=C1NC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 YMXTUQYXYGVDSZ-UHFFFAOYSA-N 0.000 claims 1
- NBKABANUFOYBEC-UHFFFAOYSA-N n-[6-(aminomethyl)-4-bromo-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(CN)=CC(Br)=C3N=2)=N1 NBKABANUFOYBEC-UHFFFAOYSA-N 0.000 claims 1
- IRUQMRLGGUBPCE-UHFFFAOYSA-N n-[6-(aminomethyl)-4-chloro-1,3-benzothiazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide Chemical compound S1C2=CC(CN)=CC(Cl)=C2N=C1NC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 IRUQMRLGGUBPCE-UHFFFAOYSA-N 0.000 claims 1
- HBPCATNHBDQBIH-UHFFFAOYSA-N n-[6-(aminomethyl)-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(CN)=CC(Cl)=C3N=2)=N1 HBPCATNHBDQBIH-UHFFFAOYSA-N 0.000 claims 1
- NPBLUDZLSPNADJ-UHFFFAOYSA-N n-[6-(aminomethyl)-4-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(CN)=CC(C)=C3N=2)=N1 NPBLUDZLSPNADJ-UHFFFAOYSA-N 0.000 claims 1
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- NVOKDHJNTDQNMA-VIFPVBQESA-N n-[6-[[[(2s)-2-aminopropanoyl]amino]methyl]-4-chloro-1,3-benzothiazol-2-yl]-5-(2-aminopyrimidin-4-yl)thiophene-2-carboxamide Chemical compound S1C2=CC(CNC(=O)[C@@H](N)C)=CC(Cl)=C2N=C1NC(=O)C(S1)=CC=C1C1=CC=NC(N)=N1 NVOKDHJNTDQNMA-VIFPVBQESA-N 0.000 claims 1
- OKZUMVGXJFQHGB-UHFFFAOYSA-N n-[7-(aminomethyl)-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=C(CN)C=CC(Cl)=C3N=2)=N1 OKZUMVGXJFQHGB-UHFFFAOYSA-N 0.000 claims 1
- KMOJYIAAOSYDMM-UHFFFAOYSA-N n-[[1-(4-chlorophenyl)cyclopropyl]methyl]-5-[2-(methylamino)pyrimidin-4-yl]thiophene-2-carboxamide Chemical compound CNC1=NC=CC(C=2SC(=CC=2)C(=O)NCC2(CC2)C=2C=CC(Cl)=CC=2)=N1 KMOJYIAAOSYDMM-UHFFFAOYSA-N 0.000 claims 1
- WRNZVLSGKACYLF-UHFFFAOYSA-N n-[[5-(2-aminopyrimidin-4-yl)thiophen-2-yl]methyl]-4-chloro-1,3-benzothiazol-2-amine Chemical compound NC1=NC=CC(C=2SC(CNC=3SC4=CC=CC(Cl)=C4N=3)=CC=2)=N1 WRNZVLSGKACYLF-UHFFFAOYSA-N 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 229960005190 phenylalanine Drugs 0.000 claims 1
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
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- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- VSCGRMUDBNQJNB-UHFFFAOYSA-N pyrimidin-2-ylcarbamic acid Chemical compound OC(=O)NC1=NC=CC=N1 VSCGRMUDBNQJNB-UHFFFAOYSA-N 0.000 claims 1
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 claims 1
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims 1
- 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 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 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
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| CN101624391A (zh) * | 2001-06-11 | 2010-01-13 | 病毒化学医药公司 | 用作黄病毒感染抗病毒剂的噻吩衍生物 |
| US7402608B2 (en) * | 2002-12-10 | 2008-07-22 | Virochem Pharma Inc. | Compounds and methods for the treatment or prevention of Flavivirus infections |
| TW200533357A (en) * | 2004-01-08 | 2005-10-16 | Millennium Pharm Inc | 2-(amino-substituted)-4-aryl pyrimidines and related compounds useful for treating inflammatory diseases |
| US20080293716A1 (en) * | 2004-01-30 | 2008-11-27 | Smithkline Beecham Corporation | Chemical Compounds |
| EP1907385A4 (en) * | 2005-07-26 | 2009-05-06 | Smithkline Beecham Corp | LINKS |
| WO2007016292A2 (en) * | 2005-07-27 | 2007-02-08 | Vertex Pharmaceuticals Incorporated | Heterocyclic amides as biofilm modulators |
| US7803806B2 (en) | 2005-11-03 | 2010-09-28 | Sgx Pharmaceuticals, Inc. | Pyrimidinyl-thiophene kinase modulators |
| MY149143A (en) * | 2006-01-18 | 2013-07-15 | Amgen Inc | Thiazole compounds as protien kinase b (pkb) inhibitors |
| AU2007208358A1 (en) | 2006-01-23 | 2007-08-02 | Vertex Pharmaceuticals Incorporated | Thiophene-carboxamides useful as inhibitors of protein kinases |
| ZA200808966B (en) * | 2006-03-27 | 2010-03-31 | Nerviano Medical Sciences Srl | Pyridyl- and pyrimidinyl-substituted pyrrole-, thiophene- and furane-derivatives as kinase inhibitors |
| EP2418210A1 (en) * | 2006-04-13 | 2012-02-15 | Vertex Pharmceuticals Incorporated | Thiophene-carboxamides useful as inhibitors of protein kinases |
| AU2007268056A1 (en) | 2006-05-23 | 2007-12-06 | Vertex Pharmaceuticals Incorporated | Thiophene-carboxamides useful as inhibitors of protein kinases |
| JP2009538309A (ja) | 2006-05-23 | 2009-11-05 | バーテックス ファーマシューティカルズ インコーポレイテッド | プロテインキナーゼのインヒビターとして有用なチオフェンカルボキサミド |
| CA2670260A1 (en) | 2006-11-15 | 2008-05-22 | Virochem Pharma Inc. | Thiophene analogues for the treatment or prevention of flavivirus infections |
| UY30892A1 (es) | 2007-02-07 | 2008-09-02 | Smithkline Beckman Corp | Inhibidores de la actividad akt |
| AU2012233017B2 (en) * | 2007-02-07 | 2013-01-10 | Novartis Ag | Inhibitors of Akt activity |
| WO2008098105A1 (en) * | 2007-02-07 | 2008-08-14 | Smithkline Beecham Corporation | Inhibitors of akt activity |
| DE102007010801A1 (de) | 2007-03-02 | 2008-09-04 | Bayer Cropscience Ag | Diaminopyrimidine als Fungizide |
| AU2008276512A1 (en) * | 2007-07-17 | 2009-01-22 | Amgen Inc. | Thiadiazole modulators of PKB |
| US7897619B2 (en) | 2007-07-17 | 2011-03-01 | Amgen Inc. | Heterocyclic modulators of PKB |
| RS54303B1 (sr) | 2007-07-19 | 2016-02-29 | Lundbeck, H., A/S | 5-člani heterociklični amidi i srodna jedinjenja |
| PL2201012T3 (pl) * | 2007-10-11 | 2014-11-28 | Astrazeneca Ab | Pochodne pirolo[2,3-d]pirymidyny jako inhibitory kinazy białkowej b |
| JP5581219B2 (ja) | 2008-01-25 | 2014-08-27 | ミレニアム ファーマシューティカルズ， インコーポレイテッド | チオフェンおよびホスファチジルイノシトール３−キナーゼ（ｐｉ３ｋ）阻害薬としてのその使用 |
| TWI426074B (zh) * | 2008-04-30 | 2014-02-11 | Nerviano Medical Sciences Srl | ５－（２－胺基－嘧啶－４－基）－２－芳基－１ｈ－吡咯－３－羧醯胺之製造方法 |
| JP2011525930A (ja) * | 2008-06-26 | 2011-09-29 | グラクソスミスクライン・リミテッド・ライアビリティ・カンパニー | Ａｋｔ活性の阻害剤 |
| EP2303852A4 (en) * | 2008-06-26 | 2011-12-28 | Glaxosmithkline Llc | ACTIVITY INHIBITORS AKT |
| EP2161259A1 (de) | 2008-09-03 | 2010-03-10 | Bayer CropScience AG | 4-Halogenalkylsubstituierte Diaminopyrimidine als Fungizide |
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2005
- 2005-03-30 MX MXPA06010520A patent/MXPA06010520A/es active IP Right Grant
- 2005-03-30 AU AU2005228899A patent/AU2005228899A1/en not_active Abandoned
- 2005-03-30 BR BRPI0508230-7A patent/BRPI0508230A/pt not_active IP Right Cessation
- 2005-03-30 US US11/095,993 patent/US7470701B2/en not_active Expired - Fee Related
- 2005-03-30 RU RU2006138036/04A patent/RU2006138036A/ru not_active Application Discontinuation
- 2005-03-30 EP EP05760186A patent/EP1732919A1/en not_active Withdrawn
- 2005-03-30 JP JP2007506511A patent/JP2007531757A/ja active Pending
- 2005-03-30 CA CA002561977A patent/CA2561977A1/en not_active Abandoned
- 2005-03-30 WO PCT/US2005/010690 patent/WO2005095386A1/en not_active Ceased
- 2005-03-30 CN CNA2005800105750A patent/CN1989131A/zh active Pending
-
2006
- 2006-08-31 IL IL177799A patent/IL177799A0/en unknown
-
2008
- 2008-05-29 US US12/129,367 patent/US20080255120A1/en not_active Abandoned
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