RU2311414C2 - Диаминотиазолы, обладающие свойствами ингибитора циклин-зависимой киназы 4 - Google Patents
Диаминотиазолы, обладающие свойствами ингибитора циклин-зависимой киназы 4 Download PDFInfo
- Publication number
- RU2311414C2 RU2311414C2 RU2004137110/04A RU2004137110A RU2311414C2 RU 2311414 C2 RU2311414 C2 RU 2311414C2 RU 2004137110/04 A RU2004137110/04 A RU 2004137110/04A RU 2004137110 A RU2004137110 A RU 2004137110A RU 2311414 C2 RU2311414 C2 RU 2311414C2
- Authority
- RU
- Russia
- Prior art keywords
- amino
- thiazol
- phenylamino
- methanone
- lower alkyl
- Prior art date
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- WKXCZMFWXZRMEZ-UHFFFAOYSA-N 1,3-thiazole-2,4-diamine Chemical class NC1=CSC(N)=N1 WKXCZMFWXZRMEZ-UHFFFAOYSA-N 0.000 title abstract 2
- 229940083347 Cyclin-dependent kinase 4 inhibitor Drugs 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract 43
- 150000001875 compounds Chemical class 0.000 claims abstract 42
- 125000004429 atom Chemical group 0.000 claims abstract 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 5
- 102000013701 Cyclin-Dependent Kinase 4 Human genes 0.000 claims abstract 5
- 108010025464 Cyclin-Dependent Kinase 4 Proteins 0.000 claims abstract 5
- 150000002148 esters Chemical class 0.000 claims abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 4
- 101150012716 CDK1 gene Proteins 0.000 claims abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- 101150073031 cdk2 gene Proteins 0.000 claims abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 63
- 229910052739 hydrogen Inorganic materials 0.000 claims 19
- 239000001257 hydrogen Substances 0.000 claims 19
- 150000002431 hydrogen Chemical class 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 7
- -1 —CF 3 Chemical group 0.000 claims 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 5
- 239000011737 fluorine Substances 0.000 claims 5
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- OVWYEQOVUDKZNU-UHFFFAOYSA-N m-tolualdehyde Chemical compound CC1=CC=CC(C=O)=C1 OVWYEQOVUDKZNU-UHFFFAOYSA-N 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- LUKXUACIWWQJHT-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound S1C(C(=O)C=2C=C(F)C=CC=2)=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCCC1 LUKXUACIWWQJHT-UHFFFAOYSA-N 0.000 claims 2
- 239000003112 inhibitor Substances 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- QBXCVQVFPVXAGS-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-bromoethanone Chemical compound BrCC(=O)C1=CC=C2OCOC2=C1 QBXCVQVFPVXAGS-UHFFFAOYSA-N 0.000 claims 1
- WUEPMEXUMQVEGN-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;2,2,2-trifluoro-n-[2-[2-[(2,2,2-trifluoroacetyl)amino]ethylamino]ethyl]acetamide Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C(=O)NCCNCCNC(=O)C(F)(F)F WUEPMEXUMQVEGN-UHFFFAOYSA-N 0.000 claims 1
- 125000003635 2-dimethylaminoethoxy group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims 1
- PQYFWQYDROQYOA-UHFFFAOYSA-N 3-[4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazole-5-carbonyl]benzonitrile Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(C=CC=2)C#N)S1 PQYFWQYDROQYOA-UHFFFAOYSA-N 0.000 claims 1
- COHGKAMBYJGYOZ-UHFFFAOYSA-N 3-cyclopropylbenzaldehyde Chemical compound O=CC1=CC=CC(C2CC2)=C1 COHGKAMBYJGYOZ-UHFFFAOYSA-N 0.000 claims 1
- PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- 102000003903 Cyclin-dependent kinases Human genes 0.000 claims 1
- 108090000266 Cyclin-dependent kinases Proteins 0.000 claims 1
- IBIXIAHOAPMZTJ-UHFFFAOYSA-N [4-amino-2-(4-piperidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(3-ethylphenyl)methanone Chemical compound CCC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OC4CNCCC4)=CC=3)S2)N)=C1 IBIXIAHOAPMZTJ-UHFFFAOYSA-N 0.000 claims 1
- SJWTXURWSJGDOI-UHFFFAOYSA-N [4-amino-2-(4-piperidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(3-fluoro-4-methoxyphenyl)methanone Chemical compound C1=C(F)C(OC)=CC=C1C(=O)C1=C(N)N=C(NC=2C=CC(OC3CNCCC3)=CC=2)S1 SJWTXURWSJGDOI-UHFFFAOYSA-N 0.000 claims 1
- FVTSKHLUDRUVSK-UHFFFAOYSA-N [4-amino-2-(4-piperidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound S1C(C(=O)C=2C=C(F)C=CC=2)=C(N)N=C1NC(C=C1)=CC=C1OC1CCCNC1 FVTSKHLUDRUVSK-UHFFFAOYSA-N 0.000 claims 1
- IFXOVSQDVVTNDS-UHFFFAOYSA-N [4-amino-2-(4-piperidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(4-hydroxy-3-propylphenyl)methanone Chemical compound C1=C(O)C(CCC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OC4CNCCC4)=CC=3)S2)N)=C1 IFXOVSQDVVTNDS-UHFFFAOYSA-N 0.000 claims 1
- BWQIMYBVXAAHBJ-UHFFFAOYSA-N [4-amino-2-(4-pyrrolidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(3-cyclopropylphenyl)methanone Chemical compound S1C(C(=O)C=2C=C(C=CC=2)C2CC2)=C(N)N=C1NC(C=C1)=CC=C1OC1CCNC1 BWQIMYBVXAAHBJ-UHFFFAOYSA-N 0.000 claims 1
- ZDUFKQZIJRVRSN-UHFFFAOYSA-N [4-amino-2-(4-pyrrolidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(3-ethylphenyl)methanone Chemical compound CCC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OC4CNCC4)=CC=3)S2)N)=C1 ZDUFKQZIJRVRSN-UHFFFAOYSA-N 0.000 claims 1
- QHFKAWDIEVTHCO-UHFFFAOYSA-N [4-amino-2-(4-pyrrolidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(3-fluoro-4-methoxyphenyl)methanone Chemical compound C1=C(F)C(OC)=CC=C1C(=O)C1=C(N)N=C(NC=2C=CC(OC3CNCC3)=CC=2)S1 QHFKAWDIEVTHCO-UHFFFAOYSA-N 0.000 claims 1
- KXUOSZRFGUIVQI-UHFFFAOYSA-N [4-amino-2-(4-pyrrolidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(3-fluoro-4-methylphenyl)methanone Chemical compound C1=C(F)C(C)=CC=C1C(=O)C1=C(N)N=C(NC=2C=CC(OC3CNCC3)=CC=2)S1 KXUOSZRFGUIVQI-UHFFFAOYSA-N 0.000 claims 1
- NFRSVKZUWBBCOO-UHFFFAOYSA-N [4-amino-2-(4-pyrrolidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound S1C(C(=O)C=2C=C(F)C=CC=2)=C(N)N=C1NC(C=C1)=CC=C1OC1CCNC1 NFRSVKZUWBBCOO-UHFFFAOYSA-N 0.000 claims 1
- DIYHPWPVOVXELI-UHFFFAOYSA-N [4-amino-2-(4-pyrrolidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OC4CNCC4)=CC=3)S2)N)=C1 DIYHPWPVOVXELI-UHFFFAOYSA-N 0.000 claims 1
- ASBJJBCTLYXARJ-UHFFFAOYSA-N [4-amino-2-(4-pyrrolidin-3-yloxyanilino)-1,3-thiazol-5-yl]-(4-hydroxy-3-propylphenyl)methanone Chemical compound C1=C(O)C(CCC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OC4CNCC4)=CC=3)S2)N)=C1 ASBJJBCTLYXARJ-UHFFFAOYSA-N 0.000 claims 1
- ZEGBKBJKJNMJPW-UHFFFAOYSA-N [4-amino-2-[4-(1-ethylpiperidin-3-yl)oxyanilino]-1,3-thiazol-5-yl]-(3-cyclopropylphenyl)methanone Chemical compound C1N(CC)CCCC1OC(C=C1)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(C=CC=2)C2CC2)S1 ZEGBKBJKJNMJPW-UHFFFAOYSA-N 0.000 claims 1
- SWUMKEFOVKMWNT-UHFFFAOYSA-N [4-amino-2-[4-(1-ethylpiperidin-3-yl)oxyanilino]-1,3-thiazol-5-yl]-(3-ethyl-4-fluorophenyl)methanone Chemical compound C1N(CC)CCCC1OC(C=C1)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(CC)C(F)=CC=2)S1 SWUMKEFOVKMWNT-UHFFFAOYSA-N 0.000 claims 1
- OLKIRKTWPIBXET-UHFFFAOYSA-N [4-amino-2-[4-(1-ethylpiperidin-3-yl)oxyanilino]-1,3-thiazol-5-yl]-(3-ethylphenyl)methanone Chemical compound C1N(CC)CCCC1OC(C=C1)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(CC)C=CC=2)S1 OLKIRKTWPIBXET-UHFFFAOYSA-N 0.000 claims 1
- KKVOJUGOEWEIOU-UHFFFAOYSA-N [4-amino-2-[4-(1-ethylpiperidin-3-yl)oxyanilino]-1,3-thiazol-5-yl]-(3-fluoro-4-hydroxyphenyl)methanone Chemical compound C1N(CC)CCCC1OC(C=C1)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C(O)=CC=2)S1 KKVOJUGOEWEIOU-UHFFFAOYSA-N 0.000 claims 1
- PTBUUYKKPMNSIC-UHFFFAOYSA-N [4-amino-2-[4-(1-ethylpiperidin-3-yl)oxyanilino]-1,3-thiazol-5-yl]-(3-fluoro-4-methylphenyl)methanone Chemical compound C1N(CC)CCCC1OC(C=C1)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C(C)=CC=2)S1 PTBUUYKKPMNSIC-UHFFFAOYSA-N 0.000 claims 1
- GHEKTLVREQLKIT-UHFFFAOYSA-N [4-amino-2-[4-(1-ethylpiperidin-3-yl)oxyanilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound C1N(CC)CCCC1OC(C=C1)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C=CC=2)S1 GHEKTLVREQLKIT-UHFFFAOYSA-N 0.000 claims 1
- ALBOVCNCPSAUSI-UHFFFAOYSA-N [4-amino-2-[4-(1-ethylpiperidin-3-yl)oxyanilino]-1,3-thiazol-5-yl]-(4-hydroxy-3-propylphenyl)methanone Chemical compound C1=C(O)C(CCC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OC4CN(CC)CCC4)=CC=3)S2)N)=C1 ALBOVCNCPSAUSI-UHFFFAOYSA-N 0.000 claims 1
- SAAADWCHXYPYBT-UHFFFAOYSA-N [4-amino-2-[4-(1-ethylpyrrolidin-3-yl)oxyanilino]-1,3-thiazol-5-yl]-(3-cyclopropylphenyl)methanone Chemical compound C1N(CC)CCC1OC(C=C1)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(C=CC=2)C2CC2)S1 SAAADWCHXYPYBT-UHFFFAOYSA-N 0.000 claims 1
- KAELTCHDLWSSKE-UHFFFAOYSA-N [4-amino-2-[4-(1-ethylpyrrolidin-3-yl)oxyanilino]-1,3-thiazol-5-yl]-(3-ethylphenyl)methanone Chemical compound C1N(CC)CCC1OC(C=C1)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(CC)C=CC=2)S1 KAELTCHDLWSSKE-UHFFFAOYSA-N 0.000 claims 1
- CENNDZYRNMUOKC-UHFFFAOYSA-N [4-amino-2-[4-(1-ethylpyrrolidin-3-yl)oxyanilino]-1,3-thiazol-5-yl]-(3-fluoro-4-methylphenyl)methanone Chemical compound C1N(CC)CCC1OC(C=C1)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C(C)=CC=2)S1 CENNDZYRNMUOKC-UHFFFAOYSA-N 0.000 claims 1
- UUMUREPIJLZIJX-UHFFFAOYSA-N [4-amino-2-[4-(1-ethylpyrrolidin-3-yl)oxyanilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound C1N(CC)CCC1OC(C=C1)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C=CC=2)S1 UUMUREPIJLZIJX-UHFFFAOYSA-N 0.000 claims 1
- NMTDYVUTYCNVNT-UHFFFAOYSA-N [4-amino-2-[4-(1-ethylpyrrolidin-3-yl)oxyanilino]-1,3-thiazol-5-yl]-(4-hydroxy-3-propylphenyl)methanone Chemical compound C1=C(O)C(CCC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OC4CN(CC)CC4)=CC=3)S2)N)=C1 NMTDYVUTYCNVNT-UHFFFAOYSA-N 0.000 claims 1
- JBEWFBPHPDHEKY-UHFFFAOYSA-N [4-amino-2-[4-(2-imidazol-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(3-methoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OCCN4C=NC=C4)=CC=3)S2)N)=C1 JBEWFBPHPDHEKY-UHFFFAOYSA-N 0.000 claims 1
- CVFSHHHSKJDYOE-UHFFFAOYSA-N [4-amino-2-[4-(2-morpholin-4-ylethoxy)anilino]-1,3-thiazol-5-yl]-(1,3-benzodioxol-5-yl)methanone Chemical compound S1C(C(=O)C=2C=C3OCOC3=CC=2)=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCOCC1 CVFSHHHSKJDYOE-UHFFFAOYSA-N 0.000 claims 1
- QMKKCOSTWZHORQ-UHFFFAOYSA-N [4-amino-2-[4-(2-morpholin-4-ylethoxy)anilino]-1,3-thiazol-5-yl]-(2,3-dihydro-1,4-benzodioxin-6-yl)methanone Chemical compound S1C(C(=O)C=2C=C3OCCOC3=CC=2)=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCOCC1 QMKKCOSTWZHORQ-UHFFFAOYSA-N 0.000 claims 1
- JQYOOPVLXZGSKP-UHFFFAOYSA-N [4-amino-2-[4-(2-morpholin-4-ylethoxy)anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound S1C(C(=O)C=2C=C(F)C=CC=2)=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCOCC1 JQYOOPVLXZGSKP-UHFFFAOYSA-N 0.000 claims 1
- MASMEBIOBMMGKM-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(1,3-benzodioxol-5-yl)methanone Chemical compound S1C(C(=O)C=2C=C3OCOC3=CC=2)=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCCC1 MASMEBIOBMMGKM-UHFFFAOYSA-N 0.000 claims 1
- RMVWQBBVMHXMQF-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(3-cyclopropylphenyl)methanone Chemical compound S1C(C(=O)C=2C=C(C=CC=2)C2CC2)=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCCC1 RMVWQBBVMHXMQF-UHFFFAOYSA-N 0.000 claims 1
- YWAKBDMZSWBMMS-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(3-ethoxyphenyl)methanone Chemical compound CCOC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OCCN4CCCC4)=CC=3)S2)N)=C1 YWAKBDMZSWBMMS-UHFFFAOYSA-N 0.000 claims 1
- KJTQECUCLSKETJ-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(3-ethyl-4-fluorophenyl)methanone Chemical compound C1=C(F)C(CC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OCCN4CCCC4)=CC=3)S2)N)=C1 KJTQECUCLSKETJ-UHFFFAOYSA-N 0.000 claims 1
- RYZRRKRPPFDTIK-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(3-ethylphenyl)methanone Chemical compound CCC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OCCN4CCCC4)=CC=3)S2)N)=C1 RYZRRKRPPFDTIK-UHFFFAOYSA-N 0.000 claims 1
- XDYNWZIICVZKBI-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(3-fluoro-4-hydroxyphenyl)methanone Chemical compound S1C(C(=O)C=2C=C(F)C(O)=CC=2)=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCCC1 XDYNWZIICVZKBI-UHFFFAOYSA-N 0.000 claims 1
- CZJMEJVHIWOBOC-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(3-methyl-2,3-dihydro-1-benzofuran-5-yl)methanone Chemical compound C1=C2C(C)COC2=CC=C1C(=O)C(=C(N=1)N)SC=1NC(C=C1)=CC=C1OCCN1CCCC1 CZJMEJVHIWOBOC-UHFFFAOYSA-N 0.000 claims 1
- RESOAIQZESAJBZ-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(3-methylphenyl)methanone Chemical compound CC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OCCN4CCCC4)=CC=3)S2)N)=C1 RESOAIQZESAJBZ-UHFFFAOYSA-N 0.000 claims 1
- MPJMUPXNCBXSED-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(4-ethyl-3-fluorophenyl)methanone Chemical compound C1=C(F)C(CC)=CC=C1C(=O)C1=C(N)N=C(NC=2C=CC(OCCN3CCCC3)=CC=2)S1 MPJMUPXNCBXSED-UHFFFAOYSA-N 0.000 claims 1
- RALWZQGWXGWCFR-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(4-hydroxy-3-propylphenyl)methanone Chemical compound C1=C(O)C(CCC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OCCN4CCCC4)=CC=3)S2)N)=C1 RALWZQGWXGWCFR-UHFFFAOYSA-N 0.000 claims 1
- LDWASAYFOGXWAO-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-(4-methoxy-3-nitrophenyl)methanone Chemical compound C1=C([N+]([O-])=O)C(OC)=CC=C1C(=O)C1=C(N)N=C(NC=2C=CC(OCCN3CCCC3)=CC=2)S1 LDWASAYFOGXWAO-UHFFFAOYSA-N 0.000 claims 1
- WDQXBUODEQGSPT-UHFFFAOYSA-N [4-amino-2-[4-(2-pyrrolidin-1-ylethoxy)anilino]-1,3-thiazol-5-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound S1C(C(=O)C=2C=C(C=CC=2)C(F)(F)F)=C(N)N=C1NC(C=C1)=CC=C1OCCN1CCCC1 WDQXBUODEQGSPT-UHFFFAOYSA-N 0.000 claims 1
- TUQRPBZGEYGHGW-UHFFFAOYSA-N [4-amino-2-[4-(3-aminopropoxy)anilino]-1,3-thiazol-5-yl]-(3-fluoro-4-methoxyphenyl)methanone Chemical compound C1=C(F)C(OC)=CC=C1C(=O)C1=C(N)N=C(NC=2C=CC(OCCCN)=CC=2)S1 TUQRPBZGEYGHGW-UHFFFAOYSA-N 0.000 claims 1
- CJUSRCPMBVBEDN-UHFFFAOYSA-N [4-amino-2-[4-(pyrrolidin-2-ylmethoxy)anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound S1C(C(=O)C=2C=C(F)C=CC=2)=C(N)N=C1NC(C=C1)=CC=C1OCC1CCCN1 CJUSRCPMBVBEDN-UHFFFAOYSA-N 0.000 claims 1
- NCLDOAPBCXAMNW-OAHLLOKOSA-N [4-amino-2-[4-[(2r)-2-(dimethylamino)propoxy]anilino]-1,3-thiazol-5-yl]-(3-cyclopropylphenyl)methanone Chemical compound C1=CC(OC[C@@H](C)N(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(C=CC=2)C2CC2)S1 NCLDOAPBCXAMNW-OAHLLOKOSA-N 0.000 claims 1
- UUQWCSLNCKAQHP-CQSZACIVSA-N [4-amino-2-[4-[(2r)-2-(dimethylamino)propoxy]anilino]-1,3-thiazol-5-yl]-(3-ethyl-4-fluorophenyl)methanone Chemical compound C1=C(F)C(CC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OC[C@@H](C)N(C)C)=CC=3)S2)N)=C1 UUQWCSLNCKAQHP-CQSZACIVSA-N 0.000 claims 1
- WTCFGJXWVHDULE-OAHLLOKOSA-N [4-amino-2-[4-[(2r)-2-(dimethylamino)propoxy]anilino]-1,3-thiazol-5-yl]-(3-ethylphenyl)methanone Chemical compound CCC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OC[C@@H](C)N(C)C)=CC=3)S2)N)=C1 WTCFGJXWVHDULE-OAHLLOKOSA-N 0.000 claims 1
- PEPFZROHPFCQPQ-CQSZACIVSA-N [4-amino-2-[4-[(2r)-2-(dimethylamino)propoxy]anilino]-1,3-thiazol-5-yl]-(3-fluoro-4-methylphenyl)methanone Chemical compound C1=CC(OC[C@@H](C)N(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C(C)=CC=2)S1 PEPFZROHPFCQPQ-CQSZACIVSA-N 0.000 claims 1
- PKHGKTDIDRERBR-CYBMUJFWSA-N [4-amino-2-[4-[(2r)-2-(dimethylamino)propoxy]anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound C1=CC(OC[C@@H](C)N(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C=CC=2)S1 PKHGKTDIDRERBR-CYBMUJFWSA-N 0.000 claims 1
- JNJCWPVQZGQMFX-OAHLLOKOSA-N [4-amino-2-[4-[(2r)-2-(dimethylamino)propoxy]anilino]-1,3-thiazol-5-yl]-(4-hydroxy-3-propylphenyl)methanone Chemical compound C1=C(O)C(CCC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OC[C@@H](C)N(C)C)=CC=3)S2)N)=C1 JNJCWPVQZGQMFX-OAHLLOKOSA-N 0.000 claims 1
- CQLWHHFYBLHEIJ-QGZVFWFLSA-N [4-amino-2-[4-[(2r)-2-pyrrolidin-1-ylpropoxy]anilino]-1,3-thiazol-5-yl]-(3-cyclopropylphenyl)methanone Chemical compound C([C@@H](C)N1CCCC1)OC(C=C1)=CC=C1NC(S1)=NC(N)=C1C(=O)C(C=1)=CC=CC=1C1CC1 CQLWHHFYBLHEIJ-QGZVFWFLSA-N 0.000 claims 1
- NUIRIOMUOLZYKJ-QGZVFWFLSA-N [4-amino-2-[4-[(2r)-2-pyrrolidin-1-ylpropoxy]anilino]-1,3-thiazol-5-yl]-(3-ethylphenyl)methanone Chemical compound CCC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OC[C@@H](C)N4CCCC4)=CC=3)S2)N)=C1 NUIRIOMUOLZYKJ-QGZVFWFLSA-N 0.000 claims 1
- OCHCZBZJAGBUPK-OAHLLOKOSA-N [4-amino-2-[4-[(2r)-2-pyrrolidin-1-ylpropoxy]anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound C([C@@H](C)N1CCCC1)OC(C=C1)=CC=C1NC(S1)=NC(N)=C1C(=O)C1=CC=CC(F)=C1 OCHCZBZJAGBUPK-OAHLLOKOSA-N 0.000 claims 1
- GLMKMNCOBCCCNY-MRXNPFEDSA-N [4-amino-2-[4-[(2r)-2-pyrrolidin-1-ylpropoxy]anilino]-1,3-thiazol-5-yl]-(3-methoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OC[C@@H](C)N4CCCC4)=CC=3)S2)N)=C1 GLMKMNCOBCCCNY-MRXNPFEDSA-N 0.000 claims 1
- KMXSHWREYZLHRF-QGZVFWFLSA-N [4-amino-2-[4-[(2r)-2-pyrrolidin-1-ylpropoxy]anilino]-1,3-thiazol-5-yl]-(4-hydroxy-3-propylphenyl)methanone Chemical compound C1=C(O)C(CCC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OC[C@@H](C)N4CCCC4)=CC=3)S2)N)=C1 KMXSHWREYZLHRF-QGZVFWFLSA-N 0.000 claims 1
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- BQUDHJBKNRWRMM-UHFFFAOYSA-N [4-amino-2-[4-[2-(diethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-fluoro-4-hydroxyphenyl)methanone Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C(O)=CC=2)S1 BQUDHJBKNRWRMM-UHFFFAOYSA-N 0.000 claims 1
- WWBQVIMIWSCQEZ-UHFFFAOYSA-N [4-amino-2-[4-[2-(diethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-fluoro-4-methoxyphenyl)methanone Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C(OC)=CC=2)S1 WWBQVIMIWSCQEZ-UHFFFAOYSA-N 0.000 claims 1
- IRQLNMKGTDYAOH-UHFFFAOYSA-N [4-amino-2-[4-[2-(diethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-methoxyphenyl)methanone Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(OC)C=CC=2)S1 IRQLNMKGTDYAOH-UHFFFAOYSA-N 0.000 claims 1
- ZUYYPVXTKZCTDZ-UHFFFAOYSA-N [4-amino-2-[4-[2-(diethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-methyl-2,3-dihydro-1-benzofuran-5-yl)methanone Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C3C(C)COC3=CC=2)S1 ZUYYPVXTKZCTDZ-UHFFFAOYSA-N 0.000 claims 1
- OGGSLOIELKUMQF-UHFFFAOYSA-N [4-amino-2-[4-[2-(diethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-methylsulfanylphenyl)methanone Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(SC)C=CC=2)S1 OGGSLOIELKUMQF-UHFFFAOYSA-N 0.000 claims 1
- PWSRPVZBXCPOSZ-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)-2-methylpropoxy]anilino]-1,3-thiazol-5-yl]-(3-cyclopropylphenyl)methanone Chemical compound C1=CC(OCC(C)(C)N(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(C=CC=2)C2CC2)S1 PWSRPVZBXCPOSZ-UHFFFAOYSA-N 0.000 claims 1
- HJXRZDYSJZIAQG-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)-2-methylpropoxy]anilino]-1,3-thiazol-5-yl]-(3-ethylphenyl)methanone Chemical compound CCC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OCC(C)(C)N(C)C)=CC=3)S2)N)=C1 HJXRZDYSJZIAQG-UHFFFAOYSA-N 0.000 claims 1
- BCHOKPPWMJKWOJ-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)-2-methylpropoxy]anilino]-1,3-thiazol-5-yl]-(3-fluoro-4-methylphenyl)methanone Chemical compound C1=CC(OCC(C)(C)N(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C(C)=CC=2)S1 BCHOKPPWMJKWOJ-UHFFFAOYSA-N 0.000 claims 1
- QWOASFZMYYNXRM-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)-2-methylpropoxy]anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound C1=CC(OCC(C)(C)N(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C=CC=2)S1 QWOASFZMYYNXRM-UHFFFAOYSA-N 0.000 claims 1
- DWEMBEFIYMPUFF-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)-2-methylpropoxy]anilino]-1,3-thiazol-5-yl]-(4-hydroxy-3-propylphenyl)methanone Chemical compound C1=C(O)C(CCC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OCC(C)(C)N(C)C)=CC=3)S2)N)=C1 DWEMBEFIYMPUFF-UHFFFAOYSA-N 0.000 claims 1
- ZUHXRBPQXZBELD-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(1,3-benzodioxol-5-yl)methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C3OCOC3=CC=2)S1 ZUHXRBPQXZBELD-UHFFFAOYSA-N 0.000 claims 1
- XWEJXUMHVXPUSS-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(2,3-dihydro-1,4-benzodioxin-6-yl)methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C3OCCOC3=CC=2)S1 XWEJXUMHVXPUSS-UHFFFAOYSA-N 0.000 claims 1
- UGIRNNLPFVHGJO-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-bromophenyl)methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(Br)C=CC=2)S1 UGIRNNLPFVHGJO-UHFFFAOYSA-N 0.000 claims 1
- RNAXYOGSJHEJAT-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-ethylphenyl)methanone Chemical compound CCC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OCCN(C)C)=CC=3)S2)N)=C1 RNAXYOGSJHEJAT-UHFFFAOYSA-N 0.000 claims 1
- KJGZHVGPHYUWRJ-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-fluoro-4-methylphenyl)methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C(C)=CC=2)S1 KJGZHVGPHYUWRJ-UHFFFAOYSA-N 0.000 claims 1
- KCLVVBCHPZJWBZ-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C=CC=2)S1 KCLVVBCHPZJWBZ-UHFFFAOYSA-N 0.000 claims 1
- VLUPPQWRQPEQRJ-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-methoxyphenyl)methanone Chemical compound COC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OCCN(C)C)=CC=3)S2)N)=C1 VLUPPQWRQPEQRJ-UHFFFAOYSA-N 0.000 claims 1
- BUMVLQOZZMNPSW-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-methylphenyl)methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(C)C=CC=2)S1 BUMVLQOZZMNPSW-UHFFFAOYSA-N 0.000 claims 1
- GVCMCRIPYSUCJX-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-nitrophenyl)methanone Chemical compound C1=CC(OCCN(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(C=CC=2)[N+]([O-])=O)S1 GVCMCRIPYSUCJX-UHFFFAOYSA-N 0.000 claims 1
- DTXMTQQZIZGTPO-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(4-hydroxy-3-propylphenyl)methanone Chemical compound C1=C(O)C(CCC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OCCN(C)C)=CC=3)S2)N)=C1 DTXMTQQZIZGTPO-UHFFFAOYSA-N 0.000 claims 1
- XWUKRJCWANUHSZ-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(4-methoxy-3-nitrophenyl)methanone Chemical compound C1=C([N+]([O-])=O)C(OC)=CC=C1C(=O)C1=C(N)N=C(NC=2C=CC(OCCN(C)C)=CC=2)S1 XWUKRJCWANUHSZ-UHFFFAOYSA-N 0.000 claims 1
- PKHGKTDIDRERBR-UHFFFAOYSA-N [4-amino-2-[4-[2-(dimethylamino)propoxy]anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound C1=CC(OCC(C)N(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C=CC=2)S1 PKHGKTDIDRERBR-UHFFFAOYSA-N 0.000 claims 1
- IWGPPWKRMBZHSQ-UHFFFAOYSA-N [4-amino-2-[4-[2-(ethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(1,3-benzodioxol-5-yl)methanone Chemical compound C1=CC(OCCNCC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C3OCOC3=CC=2)S1 IWGPPWKRMBZHSQ-UHFFFAOYSA-N 0.000 claims 1
- MDFPJKFYFFFBPM-UHFFFAOYSA-N [4-amino-2-[4-[2-(ethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(2,3-dihydro-1,4-benzodioxin-6-yl)methanone Chemical compound C1=CC(OCCNCC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C3OCCOC3=CC=2)S1 MDFPJKFYFFFBPM-UHFFFAOYSA-N 0.000 claims 1
- GLJAZVDIWLYFBM-UHFFFAOYSA-N [4-amino-2-[4-[2-(ethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(2,3-dihydro-1-benzofuran-5-yl)methanone Chemical compound C1=CC(OCCNCC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C3CCOC3=CC=2)S1 GLJAZVDIWLYFBM-UHFFFAOYSA-N 0.000 claims 1
- CIMCWUAUKUSXMB-UHFFFAOYSA-N [4-amino-2-[4-[2-(ethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-cyclopropylphenyl)methanone Chemical compound C1=CC(OCCNCC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(C=CC=2)C2CC2)S1 CIMCWUAUKUSXMB-UHFFFAOYSA-N 0.000 claims 1
- LOSSNOFDCNVJON-UHFFFAOYSA-N [4-amino-2-[4-[2-(ethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-ethyl-4-fluorophenyl)methanone Chemical compound C1=CC(OCCNCC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(CC)C(F)=CC=2)S1 LOSSNOFDCNVJON-UHFFFAOYSA-N 0.000 claims 1
- QNKLRWZNKREECZ-UHFFFAOYSA-N [4-amino-2-[4-[2-(ethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-ethylphenyl)methanone Chemical compound C1=CC(OCCNCC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(CC)C=CC=2)S1 QNKLRWZNKREECZ-UHFFFAOYSA-N 0.000 claims 1
- FIWHTKIXUIAOTG-UHFFFAOYSA-N [4-amino-2-[4-[2-(ethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-fluoro-4-methylphenyl)methanone Chemical compound C1=CC(OCCNCC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C(C)=CC=2)S1 FIWHTKIXUIAOTG-UHFFFAOYSA-N 0.000 claims 1
- PODGXWBFFFLLCT-UHFFFAOYSA-N [4-amino-2-[4-[2-(ethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound C1=CC(OCCNCC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C=CC=2)S1 PODGXWBFFFLLCT-UHFFFAOYSA-N 0.000 claims 1
- FBEOXMSYTZRCPI-UHFFFAOYSA-N [4-amino-2-[4-[2-(ethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(3-methoxyphenyl)methanone Chemical compound C1=CC(OCCNCC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(OC)C=CC=2)S1 FBEOXMSYTZRCPI-UHFFFAOYSA-N 0.000 claims 1
- XXEDJYQWHZFCKK-UHFFFAOYSA-N [4-amino-2-[4-[2-(ethylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(4-hydroxy-3-propylphenyl)methanone Chemical compound C1=C(O)C(CCC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OCCNCC)=CC=3)S2)N)=C1 XXEDJYQWHZFCKK-UHFFFAOYSA-N 0.000 claims 1
- NVPRDJYYVWXAFP-UHFFFAOYSA-N [4-amino-2-[4-[2-(propan-2-ylamino)ethoxy]anilino]-1,3-thiazol-5-yl]-(2,3-dihydro-1,4-benzodioxin-6-yl)methanone Chemical compound C1=CC(OCCNC(C)C)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C3OCCOC3=CC=2)S1 NVPRDJYYVWXAFP-UHFFFAOYSA-N 0.000 claims 1
- KACFBTLJESYLDN-UHFFFAOYSA-N [4-amino-2-[4-[3-(ethylamino)propoxy]anilino]-1,3-thiazol-5-yl]-(3-fluoro-4-methoxyphenyl)methanone Chemical compound C1=CC(OCCCNCC)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C(OC)=CC=2)S1 KACFBTLJESYLDN-UHFFFAOYSA-N 0.000 claims 1
- PNDUVXGVAYSDOC-FQEVSTJZSA-N [4-amino-2-[4-[[(2s)-1-methylpyrrolidin-2-yl]methoxy]anilino]-1,3-thiazol-5-yl]-(3-cyclopropylphenyl)methanone Chemical compound CN1CCC[C@H]1COC(C=C1)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(C=CC=2)C2CC2)S1 PNDUVXGVAYSDOC-FQEVSTJZSA-N 0.000 claims 1
- OQOXLJLEICWLTO-IBGZPJMESA-N [4-amino-2-[4-[[(2s)-1-methylpyrrolidin-2-yl]methoxy]anilino]-1,3-thiazol-5-yl]-(3-ethylphenyl)methanone Chemical compound CCC1=CC=CC(C(=O)C2=C(N=C(NC=3C=CC(OC[C@H]4N(CCC4)C)=CC=3)S2)N)=C1 OQOXLJLEICWLTO-IBGZPJMESA-N 0.000 claims 1
- PJKYZDOZWGPMPF-KRWDZBQOSA-N [4-amino-2-[4-[[(2s)-1-methylpyrrolidin-2-yl]methoxy]anilino]-1,3-thiazol-5-yl]-(3-fluoro-4-methylphenyl)methanone Chemical compound CN1CCC[C@H]1COC(C=C1)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C(C)=CC=2)S1 PJKYZDOZWGPMPF-KRWDZBQOSA-N 0.000 claims 1
- QJIDJBIONRJFKP-KRWDZBQOSA-N [4-amino-2-[4-[[(2s)-1-methylpyrrolidin-2-yl]methoxy]anilino]-1,3-thiazol-5-yl]-(3-fluorophenyl)methanone Chemical compound CN1CCC[C@H]1COC(C=C1)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C=CC=2)S1 QJIDJBIONRJFKP-KRWDZBQOSA-N 0.000 claims 1
- WYJCIMXJXJDOGR-IBGZPJMESA-N [4-amino-2-[4-[[(2s)-1-methylpyrrolidin-2-yl]methoxy]anilino]-1,3-thiazol-5-yl]-(4-hydroxy-3-propylphenyl)methanone Chemical compound C1=C(O)C(CCC)=CC(C(=O)C2=C(N=C(NC=3C=CC(OC[C@H]4N(CCC4)C)=CC=3)S2)N)=C1 WYJCIMXJXJDOGR-IBGZPJMESA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- WMHLXDXCUJYTGL-UHFFFAOYSA-N tert-butyl 3-[4-[[4-amino-5-(3-fluorobenzoyl)-1,3-thiazol-2-yl]amino]phenoxy]azetidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC1OC(C=C1)=CC=C1NC1=NC(N)=C(C(=O)C=2C=C(F)C=CC=2)S1 WMHLXDXCUJYTGL-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 206010028980 Neoplasm Diseases 0.000 abstract 2
- 230000000694 effects Effects 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 2
- 201000011510 cancer Diseases 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000001153 fluoro group Chemical group F* 0.000 abstract 1
- 230000007721 medicinal effect Effects 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/42—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38151302P | 2002-05-17 | 2002-05-17 | |
| US60/381,513 | 2002-05-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2004137110A RU2004137110A (ru) | 2005-08-20 |
| RU2311414C2 true RU2311414C2 (ru) | 2007-11-27 |
Family
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|---|---|---|---|
| RU2004137110/04A RU2311414C2 (ru) | 2002-05-17 | 2003-05-12 | Диаминотиазолы, обладающие свойствами ингибитора циклин-зависимой киназы 4 |
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|---|---|
| US (1) | US6818663B2 (https=) |
| EP (1) | EP1507530B1 (https=) |
| JP (1) | JP4308133B2 (https=) |
| KR (1) | KR100619515B1 (https=) |
| CN (1) | CN100400041C (https=) |
| AR (1) | AR040078A1 (https=) |
| AT (1) | ATE308323T1 (https=) |
| AU (1) | AU2003232754B2 (https=) |
| BR (1) | BR0310081A (https=) |
| CA (1) | CA2485367A1 (https=) |
| DE (1) | DE60302152T2 (https=) |
| ES (1) | ES2251697T3 (https=) |
| MX (1) | MXPA04011372A (https=) |
| PL (1) | PL374581A1 (https=) |
| RU (1) | RU2311414C2 (https=) |
| WO (1) | WO2003097048A1 (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2609018C2 (ru) * | 2010-08-24 | 2017-01-30 | Джи Ти Икс, ИНК. | Соединения для лечения рака |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070167329A1 (en) * | 2003-12-24 | 2007-07-19 | Bayer Cropscience Gmbh | Plant growth regulation |
| US7211576B2 (en) * | 2004-04-20 | 2007-05-01 | Hoffmann-La Roche Inc. | Diaminothiazoles |
| US7405220B2 (en) | 2004-06-09 | 2008-07-29 | Hoffmann-La Roche Inc. | Pyrazolopyrimidines |
| US7705009B2 (en) * | 2005-11-22 | 2010-04-27 | Hoffman-La Roche Inc. | 4-aminopyrimidine-5-thione derivatives |
| CA2668210C (en) | 2006-10-31 | 2013-03-12 | Schering Corporation | Anilinopiperazine derivatives and methods of use thereof |
| AR063531A1 (es) | 2006-10-31 | 2009-01-28 | Schering Corp | Derivados de anilinopiperazina y composicion farmaceutica |
| US8502401B2 (en) * | 2008-08-12 | 2013-08-06 | Delsper LP | Polymeric compositions comprising per(phenylethynyl) arene derivatives |
| WO2013074120A1 (en) | 2011-11-18 | 2013-05-23 | Greene, Tweed & Co. | Crosslinking compounds for high glass transition temperature polymers |
| CA2909683A1 (en) | 2013-04-16 | 2014-10-23 | Memorial Sloan-Kettering Cancer Center | Companion diagnostic for cdk4 inhibitors |
| WO2015051525A1 (en) * | 2013-10-11 | 2015-04-16 | Rhodia Operations | Synthesis of acetal/ketal |
| WO2017156263A1 (en) | 2016-03-09 | 2017-09-14 | Memorial Sloan-Kettering Cancer Center | Enigma and cdh18 as companion diagnostics for cdk4 inhibitors |
| WO2017158147A1 (en) | 2016-03-18 | 2017-09-21 | Savira Pharmaceuticals Gmbh | Pyrimidone derivatives and their use in the treatment, amelioration or prevention of a viral disease |
| WO2018089902A1 (en) * | 2016-11-13 | 2018-05-17 | Apogee Biotechnology Corporation | Diaminothiazole compounds, compositions and methods of use |
| CN110950848B (zh) * | 2018-09-27 | 2024-03-26 | 徐诺药业 | 新型氨基吡唑类衍生物的合成与应用 |
| AU2020266083A1 (en) | 2019-04-30 | 2021-09-23 | Instituto de Medicina Molecular João Lobo Antunes | Rank pathway inhibitors in combination with CDK inhibitors |
| WO2026024674A1 (en) | 2024-07-22 | 2026-01-29 | Genesis Therapeutics, Inc. | Methods of treating skp2-associated cancers |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2107063C1 (ru) * | 1993-12-21 | 1998-03-20 | Санофи | Аминопроизводные тиазола или их стереоизомеры или их аддитивные соли, способы их получения, фармацевтическая композиция, обладающая активностью в отношении кортикотропного гормона (crf) |
| EA003527B1 (ru) * | 1997-10-27 | 2003-06-26 | Агурон Фармасьютикалз, Инк. | Замещенные 4-аминотиазолы в качестве ингибиторов циклинзависимых киназ |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA71971C2 (en) * | 1999-06-04 | 2005-01-17 | Agoron Pharmaceuticals Inc | Diaminothiazoles, composition based thereon, a method for modulation of protein kinases activity, a method for the treatment of diseases mediated by protein kinases |
| EP1307462A2 (en) * | 2000-08-09 | 2003-05-07 | Agouron Pharmaceuticals, Inc. | Pyrazole-thiazole compounds, pharmaceutical compositions containing them, and methods of their use for inhibiting cyclin-dependent kinases |
| US6756374B2 (en) | 2001-01-22 | 2004-06-29 | Hoffmann-La Roche Inc. | Diaminothiazoles having antiproliferative activity |
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2003
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- 2003-05-12 EP EP03752731A patent/EP1507530B1/en not_active Expired - Lifetime
- 2003-05-12 AT AT03752731T patent/ATE308323T1/de not_active IP Right Cessation
- 2003-05-12 DE DE60302152T patent/DE60302152T2/de not_active Expired - Fee Related
- 2003-05-12 KR KR1020047018605A patent/KR100619515B1/ko not_active Expired - Fee Related
- 2003-05-12 AU AU2003232754A patent/AU2003232754B2/en not_active Ceased
- 2003-05-12 CN CNB038111314A patent/CN100400041C/zh not_active Expired - Fee Related
- 2003-05-12 MX MXPA04011372A patent/MXPA04011372A/es active IP Right Grant
- 2003-05-12 CA CA002485367A patent/CA2485367A1/en not_active Abandoned
- 2003-05-12 JP JP2004505047A patent/JP4308133B2/ja not_active Expired - Fee Related
- 2003-05-12 PL PL03374581A patent/PL374581A1/xx not_active Application Discontinuation
- 2003-05-12 BR BR0310081-2A patent/BR0310081A/pt not_active IP Right Cessation
- 2003-05-12 ES ES03752731T patent/ES2251697T3/es not_active Expired - Lifetime
- 2003-05-12 RU RU2004137110/04A patent/RU2311414C2/ru active
- 2003-05-12 WO PCT/EP2003/004939 patent/WO2003097048A1/en not_active Ceased
- 2003-05-15 AR ARP030101692A patent/AR040078A1/es not_active Application Discontinuation
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2107063C1 (ru) * | 1993-12-21 | 1998-03-20 | Санофи | Аминопроизводные тиазола или их стереоизомеры или их аддитивные соли, способы их получения, фармацевтическая композиция, обладающая активностью в отношении кортикотропного гормона (crf) |
| EA003527B1 (ru) * | 1997-10-27 | 2003-06-26 | Агурон Фармасьютикалз, Инк. | Замещенные 4-аминотиазолы в качестве ингибиторов циклинзависимых киназ |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2609018C2 (ru) * | 2010-08-24 | 2017-01-30 | Джи Ти Икс, ИНК. | Соединения для лечения рака |
Also Published As
| Publication number | Publication date |
|---|---|
| JP4308133B2 (ja) | 2009-08-05 |
| CA2485367A1 (en) | 2003-11-27 |
| WO2003097048A1 (en) | 2003-11-27 |
| AU2003232754A1 (en) | 2003-12-02 |
| CN1652780A (zh) | 2005-08-10 |
| RU2004137110A (ru) | 2005-08-20 |
| AR040078A1 (es) | 2005-03-16 |
| US6818663B2 (en) | 2004-11-16 |
| KR20050006261A (ko) | 2005-01-15 |
| KR100619515B1 (ko) | 2006-09-08 |
| PL374581A1 (en) | 2005-10-31 |
| ES2251697T3 (es) | 2006-05-01 |
| DE60302152T2 (de) | 2006-07-13 |
| BR0310081A (pt) | 2005-02-15 |
| DE60302152D1 (de) | 2005-12-08 |
| JP2005530783A (ja) | 2005-10-13 |
| US20040006058A1 (en) | 2004-01-08 |
| ATE308323T1 (de) | 2005-11-15 |
| EP1507530B1 (en) | 2005-11-02 |
| AU2003232754B2 (en) | 2009-03-12 |
| EP1507530A1 (en) | 2005-02-23 |
| MXPA04011372A (es) | 2005-08-15 |
| CN100400041C (zh) | 2008-07-09 |
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