JP2008500320A5 - - Google Patents
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- Publication number
- JP2008500320A5 JP2008500320A5 JP2007514117A JP2007514117A JP2008500320A5 JP 2008500320 A5 JP2008500320 A5 JP 2008500320A5 JP 2007514117 A JP2007514117 A JP 2007514117A JP 2007514117 A JP2007514117 A JP 2007514117A JP 2008500320 A5 JP2008500320 A5 JP 2008500320A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrimidin
- thiazol
- methyl
- phenyl
- amine
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 50
- 125000000217 alkyl group Chemical group 0.000 claims 48
- 229910005965 SO 2 Inorganic materials 0.000 claims 47
- -1 alkyl-R 9 Chemical group 0.000 claims 39
- 125000003118 aryl group Chemical group 0.000 claims 28
- 125000003710 aryl alkyl group Chemical group 0.000 claims 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 16
- 125000003545 alkoxy group Chemical group 0.000 claims 14
- 125000005843 halogen group Chemical group 0.000 claims 11
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 10
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 9
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
- 125000001424 substituent group Chemical group 0.000 claims 7
- 102000004190 Enzymes Human genes 0.000 claims 6
- 108090000790 Enzymes Proteins 0.000 claims 6
- 125000002723 alicyclic group Polymers 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- 229910052760 oxygen Inorganic materials 0.000 claims 6
- 125000004076 pyridyl group Chemical group 0.000 claims 6
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 5
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 5
- 150000004292 cyclic ethers Chemical class 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 5
- 208000035475 disorder Diseases 0.000 claims 5
- WMYBWPZOKYUYHQ-UHFFFAOYSA-N 1-[4-[3-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C1=CC=CC(NC=2N=C(C=CN=2)C2=C(N=C(C)S2)C)=C1 WMYBWPZOKYUYHQ-UHFFFAOYSA-N 0.000 claims 4
- ZBYYPNTVDDUJTC-UHFFFAOYSA-N 1-[4-[4-[[4-(2-amino-4-methyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound C1CN(C(=O)C)CCN1C(C=C1)=CC=C1NC1=NC=CC(C2=C(N=C(N)S2)C)=N1 ZBYYPNTVDDUJTC-UHFFFAOYSA-N 0.000 claims 4
- RPMKNQKYFFKBAZ-UHFFFAOYSA-N 1-[4-[4-[[4-[2-(ethylamino)-4-methyl-1,3-thiazol-5-yl]pyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound S1C(NCC)=NC(C)=C1C1=CC=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(C)=O)=N1 RPMKNQKYFFKBAZ-UHFFFAOYSA-N 0.000 claims 4
- DOBOZMUVNVYNLF-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(3-methyl-4-piperidin-1-ylphenyl)pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=C(C)C(N3CCCCC3)=CC=2)=N1 DOBOZMUVNVYNLF-UHFFFAOYSA-N 0.000 claims 4
- KKZLCEABFUFJHM-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(3-methylsulfonylphenyl)pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=C(C=CC=2)S(C)(=O)=O)=N1 KKZLCEABFUFJHM-UHFFFAOYSA-N 0.000 claims 4
- YNNLNAPIIVWREC-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(3-piperazin-1-ylphenyl)pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=C(C=CC=2)N2CCNCC2)=N1 YNNLNAPIIVWREC-UHFFFAOYSA-N 0.000 claims 4
- GGVWWYJGNSVOOQ-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(4-piperidin-1-ylphenyl)pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=CC(=CC=2)N2CCCCC2)=N1 GGVWWYJGNSVOOQ-UHFFFAOYSA-N 0.000 claims 4
- MSLDXLIUSOSHSA-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-(4-thiomorpholin-4-ylphenyl)pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=CC(=CC=2)N2CCSCC2)=N1 MSLDXLIUSOSHSA-UHFFFAOYSA-N 0.000 claims 4
- GMRHSZXJSJNDHZ-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-[3-(morpholin-4-ylmethyl)phenyl]pyrimidin-2-amine Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=C(CN3CCOCC3)C=CC=2)=N1 GMRHSZXJSJNDHZ-UHFFFAOYSA-N 0.000 claims 4
- SXGSWCDDSRJDTO-UHFFFAOYSA-N 4-(2,4-dimethyl-1,3-thiazol-5-yl)-n-[4-methoxy-3-(morpholin-4-ylmethyl)phenyl]pyrimidin-2-amine Chemical compound C1=C(CN2CCOCC2)C(OC)=CC=C1NC(N=1)=NC=CC=1C=1SC(C)=NC=1C SXGSWCDDSRJDTO-UHFFFAOYSA-N 0.000 claims 4
- YJJKMZKHSQMMTM-UHFFFAOYSA-N 4-[4-methyl-2-(thiophen-2-ylsulfonylmethyl)-1,3-thiazol-5-yl]-n-(4-morpholin-4-ylphenyl)pyrimidin-2-amine Chemical compound S1C(C=2N=C(NC=3C=CC(=CC=3)N3CCOCC3)N=CC=2)=C(C)N=C1CS(=O)(=O)C1=CC=CS1 YJJKMZKHSQMMTM-UHFFFAOYSA-N 0.000 claims 4
- QOBGKWWRAPVAHZ-UHFFFAOYSA-N 4-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]-2-(morpholin-4-ylmethyl)phenol Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=C(CN3CCOCC3)C(O)=CC=2)=N1 QOBGKWWRAPVAHZ-UHFFFAOYSA-N 0.000 claims 4
- YGXOMEYMYMUEEV-UHFFFAOYSA-N 4-methyl-5-[2-(3-methyl-4-piperidin-1-ylanilino)pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound N1=C(N)SC(C=2N=C(NC=3C=C(C)C(N4CCCCC4)=CC=3)N=CC=2)=C1C YGXOMEYMYMUEEV-UHFFFAOYSA-N 0.000 claims 4
- WIRNEQAIBUAVLP-UHFFFAOYSA-N 4-methyl-5-[2-(4-piperazin-1-ylanilino)pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound N1=C(N)SC(C=2N=C(NC=3C=CC(=CC=3)N3CCNCC3)N=CC=2)=C1C WIRNEQAIBUAVLP-UHFFFAOYSA-N 0.000 claims 4
- XGOQGRONEKZZQT-UHFFFAOYSA-N 4-methyl-5-[2-(4-piperidin-1-ylanilino)pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound N1=C(N)SC(C=2N=C(NC=3C=CC(=CC=3)N3CCCCC3)N=CC=2)=C1C XGOQGRONEKZZQT-UHFFFAOYSA-N 0.000 claims 4
- AJVAMKMZGVKFMK-UHFFFAOYSA-N 4-methyl-5-[2-(4-thiomorpholin-4-ylanilino)pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound N1=C(N)SC(C=2N=C(NC=3C=CC(=CC=3)N3CCSCC3)N=CC=2)=C1C AJVAMKMZGVKFMK-UHFFFAOYSA-N 0.000 claims 4
- LRWFZAGCWBXQDC-UHFFFAOYSA-N 4-n-[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]-1-n-methyl-2-(trifluoromethyl)benzene-1,4-diamine Chemical compound C1=C(C(F)(F)F)C(NC)=CC=C1NC1=NC=CC(C2=C(N=C(C)S2)C)=N1 LRWFZAGCWBXQDC-UHFFFAOYSA-N 0.000 claims 4
- YOLKAZLNKSERGQ-UHFFFAOYSA-N 5-[2-(3-methoxy-4-morpholin-4-ylanilino)pyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C=1C=C(N2CCOCC2)C(OC)=CC=1NC(N=1)=NC=CC=1C=1SC(N)=NC=1C YOLKAZLNKSERGQ-UHFFFAOYSA-N 0.000 claims 4
- OOCUBFRMWPHCEE-UHFFFAOYSA-N 5-[2-[4-(4-benzylpiperazin-1-yl)anilino]pyrimidin-4-yl]-n-ethyl-4-methyl-1,3-thiazol-2-amine Chemical compound S1C(NCC)=NC(C)=C1C1=CC=NC(NC=2C=CC(=CC=2)N2CCN(CC=3C=CC=CC=3)CC2)=N1 OOCUBFRMWPHCEE-UHFFFAOYSA-N 0.000 claims 4
- 108091007914 CDKs Proteins 0.000 claims 4
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims 4
- ZDNIYSVIOJWIRR-UHFFFAOYSA-N [3-(hydroxymethyl)-5-[[4-[4-methyl-2-(methylamino)-1,3-thiazol-5-yl]pyrimidin-2-yl]amino]phenyl]methanol Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=C(CO)C=C(CO)C=2)=N1 ZDNIYSVIOJWIRR-UHFFFAOYSA-N 0.000 claims 4
- ZYHPYQACTSXUDE-UHFFFAOYSA-N [3-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]-5-(hydroxymethyl)phenyl]methanol Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=C(CO)C=C(CO)C=2)=N1 ZYHPYQACTSXUDE-UHFFFAOYSA-N 0.000 claims 4
- LJKQHMFUGPKGDU-UHFFFAOYSA-N [4-methyl-5-[2-(3-methyl-4-piperidin-1-ylanilino)pyrimidin-4-yl]-1,3-thiazol-2-yl]methanol Chemical compound N1=C(CO)SC(C=2N=C(NC=3C=C(C)C(N4CCCCC4)=CC=3)N=CC=2)=C1C LJKQHMFUGPKGDU-UHFFFAOYSA-N 0.000 claims 4
- GQSACQZGAVTUSA-UHFFFAOYSA-N [4-methyl-5-[2-(4-piperidin-1-ylanilino)pyrimidin-4-yl]-1,3-thiazol-2-yl]methanol Chemical compound N1=C(CO)SC(C=2N=C(NC=3C=CC(=CC=3)N3CCCCC3)N=CC=2)=C1C GQSACQZGAVTUSA-UHFFFAOYSA-N 0.000 claims 4
- HSLPGZVMVMTNLG-UHFFFAOYSA-N [5-[2-(3-methoxy-4-morpholin-4-ylanilino)pyrimidin-4-yl]-4-methyl-1,3-thiazol-2-yl]methanol Chemical compound C=1C=C(N2CCOCC2)C(OC)=CC=1NC(N=1)=NC=CC=1C=1SC(CO)=NC=1C HSLPGZVMVMTNLG-UHFFFAOYSA-N 0.000 claims 4
- 125000001931 aliphatic group Polymers 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- HVESLTJNPMAQNR-UHFFFAOYSA-N cyclopropyl-[4-[4-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]phenyl]piperazin-1-yl]methanone Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=CC(=CC=2)N2CCN(CC2)C(=O)C2CC2)=N1 HVESLTJNPMAQNR-UHFFFAOYSA-N 0.000 claims 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims 4
- 125000001033 ether group Chemical group 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000005842 heteroatom Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- BFQBIVCJNIEQPK-UHFFFAOYSA-N n,4-dimethyl-5-[2-(3-methylsulfonylanilino)pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=C(C=CC=2)S(C)(=O)=O)=N1 BFQBIVCJNIEQPK-UHFFFAOYSA-N 0.000 claims 4
- VLPMVKQWBBVWGZ-UHFFFAOYSA-N n,4-dimethyl-5-[2-(3-piperazin-1-ylanilino)pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=C(C=CC=2)N2CCNCC2)=N1 VLPMVKQWBBVWGZ-UHFFFAOYSA-N 0.000 claims 4
- YLBFCKJSKYBEIA-UHFFFAOYSA-N n,4-dimethyl-5-[2-(4-methylsulfonylanilino)pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=CC(=CC=2)S(C)(=O)=O)=N1 YLBFCKJSKYBEIA-UHFFFAOYSA-N 0.000 claims 4
- CHWONMDPHRERMK-UHFFFAOYSA-N n,4-dimethyl-5-[2-[4-(4-methylpiperazin-1-yl)anilino]pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=CC(=CC=2)N2CCN(C)CC2)=N1 CHWONMDPHRERMK-UHFFFAOYSA-N 0.000 claims 4
- QWDFRAOGDXXNAM-UHFFFAOYSA-N n-(3-methoxy-4-morpholin-4-ylphenyl)-4-(4-methyl-2-pyridin-3-yl-1,3-thiazol-5-yl)pyrimidin-2-amine Chemical compound C=1C=C(N2CCOCC2)C(OC)=CC=1NC(N=1)=NC=CC=1C(=C(N=1)C)SC=1C1=CC=CN=C1 QWDFRAOGDXXNAM-UHFFFAOYSA-N 0.000 claims 4
- OJNPFEPSIXIFKN-UHFFFAOYSA-N n-[4-(2,6-dimethylmorpholin-4-yl)phenyl]-4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-amine Chemical compound C1C(C)OC(C)CN1C(C=C1)=CC=C1NC1=NC=CC(C2=C(N=C(C)S2)C)=N1 OJNPFEPSIXIFKN-UHFFFAOYSA-N 0.000 claims 4
- ZSIXBFIBEOQNSX-UHFFFAOYSA-N n-[[3-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]phenyl]methyl]-1,1,1-trifluoromethanesulfonamide Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=C(CNS(=O)(=O)C(F)(F)F)C=CC=2)=N1 ZSIXBFIBEOQNSX-UHFFFAOYSA-N 0.000 claims 4
- VDMDIBJEXQVBAV-UHFFFAOYSA-N n-[[3-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]phenyl]methyl]benzamide Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=C(CNC(=O)C=3C=CC=CC=3)C=CC=2)=N1 VDMDIBJEXQVBAV-UHFFFAOYSA-N 0.000 claims 4
- SGOOKXXNYMRRDT-UHFFFAOYSA-N n-[[3-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]phenyl]methyl]methanesulfonamide Chemical compound S1C(C)=NC(C)=C1C1=CC=NC(NC=2C=C(CNS(C)(=O)=O)C=CC=2)=N1 SGOOKXXNYMRRDT-UHFFFAOYSA-N 0.000 claims 4
- MKZYCKFHJVCYGG-UHFFFAOYSA-N n-[[3-[[4-(2-amino-4-methyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]phenyl]methyl]-1,1,1-trifluoromethanesulfonamide Chemical compound N1=C(N)SC(C=2N=C(NC=3C=C(CNS(=O)(=O)C(F)(F)F)C=CC=3)N=CC=2)=C1C MKZYCKFHJVCYGG-UHFFFAOYSA-N 0.000 claims 4
- KDRXPXTYLVINKS-UHFFFAOYSA-N n-[[3-[[4-(2-amino-4-methyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]phenyl]methyl]methanesulfonamide Chemical compound N1=C(N)SC(C=2N=C(NC=3C=C(CNS(C)(=O)=O)C=CC=3)N=CC=2)=C1C KDRXPXTYLVINKS-UHFFFAOYSA-N 0.000 claims 4
- QHONPBKEQDOAJS-UHFFFAOYSA-N n-[[3-[[4-[2-(ethylamino)-4-methyl-1,3-thiazol-5-yl]pyrimidin-2-yl]amino]phenyl]methyl]-1,1,1-trifluoromethanesulfonamide Chemical compound S1C(NCC)=NC(C)=C1C1=CC=NC(NC=2C=C(CNS(=O)(=O)C(F)(F)F)C=CC=2)=N1 QHONPBKEQDOAJS-UHFFFAOYSA-N 0.000 claims 4
- VDUVNFOVCLKZJU-UHFFFAOYSA-N n-[[3-[[4-[2-(ethylamino)-4-methyl-1,3-thiazol-5-yl]pyrimidin-2-yl]amino]phenyl]methyl]methanesulfonamide Chemical compound S1C(NCC)=NC(C)=C1C1=CC=NC(NC=2C=C(CNS(C)(=O)=O)C=CC=2)=N1 VDUVNFOVCLKZJU-UHFFFAOYSA-N 0.000 claims 4
- IMPXANVMKWVJJQ-UHFFFAOYSA-N n-[[4-[[4-(2,4-dimethyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]phenyl]methyl]acetamide Chemical compound C1=CC(CNC(=O)C)=CC=C1NC1=NC=CC(C2=C(N=C(C)S2)C)=N1 IMPXANVMKWVJJQ-UHFFFAOYSA-N 0.000 claims 4
- ZGIRUXCIRPWULG-UHFFFAOYSA-N n-[[4-[[4-(2-amino-4-methyl-1,3-thiazol-5-yl)pyrimidin-2-yl]amino]phenyl]methyl]acetamide Chemical compound C1=CC(CNC(=O)C)=CC=C1NC1=NC=CC(C2=C(N=C(N)S2)C)=N1 ZGIRUXCIRPWULG-UHFFFAOYSA-N 0.000 claims 4
- VEJCMMPVTMQFME-UHFFFAOYSA-N n-[[4-[[4-[2-(ethylamino)-4-methyl-1,3-thiazol-5-yl]pyrimidin-2-yl]amino]phenyl]methyl]acetamide Chemical compound S1C(NCC)=NC(C)=C1C1=CC=NC(NC=2C=CC(CNC(C)=O)=CC=2)=N1 VEJCMMPVTMQFME-UHFFFAOYSA-N 0.000 claims 4
- IZUCAZPNDUNAOT-UHFFFAOYSA-N n-[[4-[[4-[4-methyl-2-(methylamino)-1,3-thiazol-5-yl]pyrimidin-2-yl]amino]phenyl]methyl]acetamide Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=CC(CNC(C)=O)=CC=2)=N1 IZUCAZPNDUNAOT-UHFFFAOYSA-N 0.000 claims 4
- FIIVFWBKGOOXBG-UHFFFAOYSA-N n-benzyl-4-methyl-5-[2-(4-morpholin-4-ylanilino)pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound S1C(C=2N=C(NC=3C=CC(=CC=3)N3CCOCC3)N=CC=2)=C(C)N=C1NCC1=CC=CC=C1 FIIVFWBKGOOXBG-UHFFFAOYSA-N 0.000 claims 4
- WBZISVWUTDVGGZ-UHFFFAOYSA-N n-ethyl-4-methyl-5-[2-(3-methyl-4-piperidin-1-ylanilino)pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound S1C(NCC)=NC(C)=C1C1=CC=NC(NC=2C=C(C)C(N3CCCCC3)=CC=2)=N1 WBZISVWUTDVGGZ-UHFFFAOYSA-N 0.000 claims 4
- XUKYEEYMPUGKNF-UHFFFAOYSA-N n-ethyl-4-methyl-5-[2-(3-methylsulfonylanilino)pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound S1C(NCC)=NC(C)=C1C1=CC=NC(NC=2C=C(C=CC=2)S(C)(=O)=O)=N1 XUKYEEYMPUGKNF-UHFFFAOYSA-N 0.000 claims 4
- YLZOUCKPNFYBKL-UHFFFAOYSA-N n-ethyl-4-methyl-5-[2-(4-methylsulfonylanilino)pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound S1C(NCC)=NC(C)=C1C1=CC=NC(NC=2C=CC(=CC=2)S(C)(=O)=O)=N1 YLZOUCKPNFYBKL-UHFFFAOYSA-N 0.000 claims 4
- GUFQYCOGYHRMAZ-UHFFFAOYSA-N n-ethyl-4-methyl-5-[2-(4-piperazin-1-ylanilino)pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound S1C(NCC)=NC(C)=C1C1=CC=NC(NC=2C=CC(=CC=2)N2CCNCC2)=N1 GUFQYCOGYHRMAZ-UHFFFAOYSA-N 0.000 claims 4
- SEDNPAMEXQDTDN-UHFFFAOYSA-N n-ethyl-4-methyl-5-[2-(4-piperidin-1-ylanilino)pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound S1C(NCC)=NC(C)=C1C1=CC=NC(NC=2C=CC(=CC=2)N2CCCCC2)=N1 SEDNPAMEXQDTDN-UHFFFAOYSA-N 0.000 claims 4
- IULWJMBPGCCACX-UHFFFAOYSA-N n-ethyl-4-methyl-5-[2-(4-thiomorpholin-4-ylanilino)pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound S1C(NCC)=NC(C)=C1C1=CC=NC(NC=2C=CC(=CC=2)N2CCSCC2)=N1 IULWJMBPGCCACX-UHFFFAOYSA-N 0.000 claims 4
- VNHYQYPOPAKUSF-UHFFFAOYSA-N n-ethyl-5-[2-(3-methoxy-4-morpholin-4-ylanilino)pyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound S1C(NCC)=NC(C)=C1C1=CC=NC(NC=2C=C(OC)C(N3CCOCC3)=CC=2)=N1 VNHYQYPOPAKUSF-UHFFFAOYSA-N 0.000 claims 4
- BFVATTPOPABDOP-UHFFFAOYSA-N n-ethyl-n,4-dimethyl-5-[2-(4-morpholin-4-ylanilino)pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound S1C(N(C)CC)=NC(C)=C1C1=CC=NC(NC=2C=CC(=CC=2)N2CCOCC2)=N1 BFVATTPOPABDOP-UHFFFAOYSA-N 0.000 claims 4
- 108090000765 processed proteins & peptides Chemical class 0.000 claims 4
- 150000003839 salts Chemical class 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- ZOMIHFOYONJRJB-UHFFFAOYSA-N 1-[4-[3-[[4-[4-methyl-2-(methylamino)-1,3-thiazol-5-yl]pyrimidin-2-yl]amino]phenyl]piperazin-1-yl]ethanone Chemical compound S1C(NC)=NC(C)=C1C1=CC=NC(NC=2C=C(C=CC=2)N2CCN(CC2)C(C)=O)=N1 ZOMIHFOYONJRJB-UHFFFAOYSA-N 0.000 claims 3
- 102000003989 Aurora kinases Human genes 0.000 claims 3
- 108090000433 Aurora kinases Proteins 0.000 claims 3
- 108091007911 GSKs Proteins 0.000 claims 3
- 102000038624 GSKs Human genes 0.000 claims 3
- 125000001072 heteroaryl group Chemical group 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
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- JFIZCDBJOWLTKX-UHFFFAOYSA-N n-[[3-[[4-[2-(3,5-dichloro-n-methylanilino)-4-methyl-1,3-thiazol-5-yl]pyrimidin-2-yl]amino]phenyl]methyl]acetamide Chemical compound C=1C(Cl)=CC(Cl)=CC=1N(C)C(S1)=NC(C)=C1C(N=1)=CC=NC=1NC1=CC=CC(CNC(C)=O)=C1 JFIZCDBJOWLTKX-UHFFFAOYSA-N 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 230000000414 obstructive effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 108010056274 polo-like kinase 1 Proteins 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
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| PCT/GB2005/002134 WO2005116025A2 (en) | 2004-05-26 | 2005-05-26 | 2-substituted-4-heteroaryl-pyrimidines useful for the treatment of proliferative disorders |
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| IL (1) | IL179508A0 (OSRAM) |
| MX (1) | MXPA06013632A (OSRAM) |
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| GB0205693D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
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| GB0205688D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
| GB0205690D0 (en) | 2002-03-09 | 2002-04-24 | Astrazeneca Ab | Chemical compounds |
| GB0311276D0 (en) | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
| GB0311274D0 (en) | 2003-05-16 | 2003-06-18 | Astrazeneca Ab | Chemical compounds |
| CA2583812A1 (en) * | 2004-10-28 | 2006-05-11 | Irm Llc | Compounds and compositions as hedgehog pathway modulators |
| JP5186219B2 (ja) | 2005-01-25 | 2013-04-17 | エピックス デラウェア， インコーポレイテッド | 置換アリールアミン化合物および５−ｈｔ６調節因子としてのその使用 |
| CN101203500B (zh) * | 2005-01-25 | 2013-08-21 | 格利尼公司 | 取代的芳胺化合物和它们作为5-ht6调节剂的用途 |
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| WO2007132221A1 (en) * | 2006-05-12 | 2007-11-22 | Cyclacel Limited | Combined anticancer pyrimidine-thiazole aurora kinase inhibitors |
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| EP2231625A4 (en) * | 2007-12-13 | 2010-12-29 | Glaxosmithkline Llc | KINASE INHIBITORS BASED ON THIAZOLE AND OXAZOLE |
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| GB0805477D0 (en) * | 2008-03-26 | 2008-04-30 | Univ Nottingham | Pyrimidines triazines and their use as pharmaceutical agents |
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| EP2483406A2 (en) | 2009-09-30 | 2012-08-08 | President and Fellows of Harvard College | Methods for modulation of autophagy through the modulation of autophagy-inhibiting gene products |
| EP2498608A4 (en) * | 2009-11-10 | 2013-04-24 | Glaxosmithkline Llc | BENZOLSULFONAMIDE THIAZOL AND OXAZOLE COMPOUNDS |
| US9180127B2 (en) | 2009-12-29 | 2015-11-10 | Dana-Farber Cancer Institute, Inc. | Type II Raf kinase inhibitors |
| BR112013021537B1 (pt) * | 2011-02-24 | 2021-08-10 | Nerviano Medical Sciences S.R.L. | Derivados de tiazolilpenil-benzenosulfonamido como inibidores da quinase |
| WO2013059634A1 (en) | 2011-10-20 | 2013-04-25 | The Regents Of The University Of California | Use of cdk9 inhibitors to reduce cartilage degradation |
| EP3569598A1 (en) * | 2011-11-17 | 2019-11-20 | Dana Farber Cancer Institute, Inc. | Inhibitors of c-jun-n-terminal kinase (jnk) |
| EP2909194A1 (en) | 2012-10-18 | 2015-08-26 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinase 7 (cdk7) |
| US9758522B2 (en) | 2012-10-19 | 2017-09-12 | Dana-Farber Cancer Institute, Inc. | Hydrophobically tagged small molecules as inducers of protein degradation |
| WO2014063054A1 (en) | 2012-10-19 | 2014-04-24 | Dana-Farber Cancer Institute, Inc. | Bone marrow on x chromosome kinase (bmx) inhibitors and uses thereof |
| JP6491202B2 (ja) | 2013-10-18 | 2019-03-27 | デイナ ファーバー キャンサー インスティチュート，インコーポレイテッド | サイクリン依存性キナーゼ７（ｃｄｋ７）の多環阻害剤 |
| WO2015058126A1 (en) | 2013-10-18 | 2015-04-23 | Syros Pharmaceuticals, Inc. | Heteroaromatic compounds useful for the treatment of prolferative diseases |
| RS58175B1 (sr) * | 2014-04-04 | 2019-03-29 | Syros Pharmaceuticals Inc | Inhibitori ciklin-zavisne kinaze 7 (cdk7) |
| US10017477B2 (en) | 2014-04-23 | 2018-07-10 | Dana-Farber Cancer Institute, Inc. | Janus kinase inhibitors and uses thereof |
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| US10300073B2 (en) | 2014-10-14 | 2019-05-28 | The Regents Of The University Of California | Use of CDK9 and BRD4 inhibitors to inhibit inflammation |
| HK1245260A1 (zh) | 2014-12-23 | 2018-08-24 | Dana-Farber Cancer Institute, Inc. | 细胞周期蛋白依赖性激酶7(cdk7)的抑制剂 |
| JP6861166B2 (ja) | 2015-03-27 | 2021-04-21 | ダナ−ファーバー キャンサー インスティテュート， インコーポレイテッド | サイクリン依存性キナーゼの阻害剤 |
| CA2986441A1 (en) | 2015-06-12 | 2016-12-15 | Dana-Farber Cancer Institute, Inc. | Combination therapy of transcription inhibitors and kinase inhibitors |
| CN113336746A (zh) | 2015-08-04 | 2021-09-03 | 常州千红生化制药股份有限公司 | N-(吡啶-2-基)-4-(噻唑-5-基)嘧啶-2-胺类化合物作为治疗性化合物 |
| US11142507B2 (en) | 2015-09-09 | 2021-10-12 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinases |
| CN111757881B (zh) * | 2018-01-15 | 2024-05-07 | 澳升医药公司 | 作为治疗剂的5-(嘧啶-4-基)噻唑-2-基脲衍生物 |
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| CN111039941B (zh) * | 2018-10-12 | 2023-03-21 | 上海医药集团股份有限公司 | 一种含氮杂环化合物、其制备方法及应用 |
| CA3124422A1 (en) | 2018-12-28 | 2020-07-02 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinase 7 and uses thereof |
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| CN116903592B (zh) * | 2023-07-13 | 2025-08-01 | 特科罗生物科技(成都)有限公司 | 一种嘧啶胺类nuak抑制剂及其制备方法和用途 |
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| US5516775A (en) * | 1992-08-31 | 1996-05-14 | Ciba-Geigy Corporation | Further use of pyrimidine derivatives |
| PL313973A1 (en) * | 1993-10-12 | 1996-08-05 | Du Pont Merck Pharma | 1 n-alkyl-n-arylopyrimidin amines and their derivatives |
| GB9519275D0 (en) * | 1995-09-21 | 1995-11-22 | Univ Dundee | Substances and their therapeutic use |
| GB9523675D0 (en) * | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| DE69736351D1 (de) * | 1996-05-08 | 2006-08-31 | Cyclacel Ltd | Methoden und mittel zur hemmung der cdk4-aktivität |
| US6703395B2 (en) * | 1998-03-04 | 2004-03-09 | Institute Of Experimental Botany Of The Academy Of Sciences Of The Czech Republic | Cyclin dependent kinase inhibitor |
| CA2231005A1 (en) * | 1998-03-04 | 1999-09-04 | Libor Havlicek | Cyclin dependent kinase inhibitor |
| CN1312807A (zh) * | 1998-06-19 | 2001-09-12 | 希龙公司 | 糖元合成酶激酶3的抑制剂 |
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| GB0107901D0 (en) * | 2001-03-29 | 2001-05-23 | Cyclacel Ltd | Anti-cancer compounds |
| DE60214703T2 (de) * | 2001-06-01 | 2007-09-13 | Vertex Pharmaceuticals Inc., Cambridge | Thiazolverbindungen, die sich als inhibitoren von proteinkinasen eignen |
| US20040181066A1 (en) * | 2001-08-01 | 2004-09-16 | Fraley Mark E. | Tyrosine kinase inhibitors |
| IL161092A0 (en) * | 2001-09-28 | 2004-08-31 | Cyclacel Ltd | N-(4-(4-methylthiazol-5-yl) pyrimidin-2-yl)-n-phenylamines as antiproliferative compounds |
| GB0226582D0 (en) * | 2002-11-14 | 2002-12-18 | Cyclacel Ltd | Anti-viral compounds |
| GB0226583D0 (en) * | 2002-11-14 | 2002-12-18 | Cyclacel Ltd | Compounds |
| GB0229581D0 (en) * | 2002-12-19 | 2003-01-22 | Cyclacel Ltd | Use |
| US20040235834A1 (en) * | 2003-03-25 | 2004-11-25 | Farmer Luc J. | Thiazoles useful as inhibitors of protein kinases |
| JP2007500179A (ja) * | 2003-07-30 | 2007-01-11 | サイクラセル・リミテッド | キナーゼ阻害剤としての２−アミノフェニル−４−フェニルピリミジン |
| JP2007500178A (ja) * | 2003-07-30 | 2007-01-11 | サイクラセル・リミテッド | プロテインキナーゼ阻害剤としてのピリジニルアミノ−ピリミジン誘導体 |
| JP5164380B2 (ja) * | 2003-10-21 | 2013-03-21 | サイクラセル リミテッド | ピリミジン−４−イル−３，４−チオン化合物及び治療におけるその使用 |
| WO2005113550A1 (ja) * | 2004-05-20 | 2005-12-01 | Mitsubishi Pharma Corporation | アミノピリミジン誘導体及びその医薬としての用途 |
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2004
- 2004-05-26 GB GBGB0411791.7A patent/GB0411791D0/en not_active Ceased
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2005
- 2005-05-26 CA CA002566051A patent/CA2566051A1/en not_active Abandoned
- 2005-05-26 CN CNA2005800241399A patent/CN1989138A/zh active Pending
- 2005-05-26 US US11/596,740 patent/US20090137572A1/en not_active Abandoned
- 2005-05-26 JP JP2007514117A patent/JP5026259B2/ja not_active Expired - Fee Related
- 2005-05-26 EP EP05748147A patent/EP1756098A2/en not_active Withdrawn
- 2005-05-26 BR BRPI0511616-3A patent/BRPI0511616A/pt not_active IP Right Cessation
- 2005-05-26 WO PCT/GB2005/002134 patent/WO2005116025A2/en not_active Ceased
- 2005-05-26 AU AU2005247682A patent/AU2005247682A1/en not_active Abandoned
- 2005-05-26 MX MXPA06013632A patent/MXPA06013632A/es not_active Application Discontinuation
-
2006
- 2006-11-22 IL IL179508A patent/IL179508A0/en unknown
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