JP2017530962A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2017530962A5 JP2017530962A5 JP2017514825A JP2017514825A JP2017530962A5 JP 2017530962 A5 JP2017530962 A5 JP 2017530962A5 JP 2017514825 A JP2017514825 A JP 2017514825A JP 2017514825 A JP2017514825 A JP 2017514825A JP 2017530962 A5 JP2017530962 A5 JP 2017530962A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- amino
- indazol
- difluoro
- phenoxy
- 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
Links
- 150000001875 compounds Chemical class 0.000 claims description 39
- 150000003839 salts Chemical class 0.000 claims description 36
- -1 C 1 -C 4 - alkoxy Chemical group 0.000 claims description 35
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 32
- 150000001204 N-oxides Chemical class 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 5
- MCAHKQZJTSJTMD-QGZVFWFLSA-N (2R)-3-[3,5-difluoro-4-[[3-[5-methoxy-4-[(3-methoxypyridin-4-yl)amino]pyrimidin-2-yl]indazol-1-yl]methyl]phenoxy]-2-methylpropan-1-ol Chemical compound FC=1C=C(OC[C@@H](CO)C)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=C(C=NC=C1)OC)OC)F MCAHKQZJTSJTMD-QGZVFWFLSA-N 0.000 claims description 4
- TWGTVRYYTDSEDP-UHFFFAOYSA-N 2-[3,5-difluoro-4-[[3-[5-methoxy-4-[(2-methylpyrimidin-4-yl)amino]pyrimidin-2-yl]indazol-1-yl]methyl]phenoxy]ethanol Chemical compound COC1=CN=C(N=C1NC1=CC=NC(C)=N1)C1=NN(CC2=C(F)C=C(OCCO)C=C2F)C2=C1C=CC=C2 TWGTVRYYTDSEDP-UHFFFAOYSA-N 0.000 claims description 4
- SYNHBBSXFBGUNB-UHFFFAOYSA-N C1(CC1)C=1C=NC=CC=1NC1=NC(=NC=C1OC)C1=NN(C2=CC=CC=C12)CC1=C(C=C(OCCO)C=C1F)F Chemical compound C1(CC1)C=1C=NC=CC=1NC1=NC(=NC=C1OC)C1=NN(C2=CC=CC=C12)CC1=C(C=C(OCCO)C=C1F)F SYNHBBSXFBGUNB-UHFFFAOYSA-N 0.000 claims description 4
- VHFSNHDRBRBTHZ-UHFFFAOYSA-N C1(CC1)NC(=O)NC1=NC=CC(=C1)NC1=NC(=NC=C1OC)C1=NN(C2=CC=CC=C12)CC1=C(C=C(C=C1F)OCCO)F Chemical compound C1(CC1)NC(=O)NC1=NC=CC(=C1)NC1=NC(=NC=C1OC)C1=NN(C2=CC=CC=C12)CC1=C(C=C(C=C1F)OCCO)F VHFSNHDRBRBTHZ-UHFFFAOYSA-N 0.000 claims description 4
- DWTOTPJNRNGNOI-UHFFFAOYSA-N CC1=NC(=CC(=N1)NC1=NC(=NC=C1OC)C1=NN(C2=CC=CC=C12)CC1=C(C=C(OCCO)C=C1F)F)C Chemical compound CC1=NC(=CC(=N1)NC1=NC(=NC=C1OC)C1=NN(C2=CC=CC=C12)CC1=C(C=C(OCCO)C=C1F)F)C DWTOTPJNRNGNOI-UHFFFAOYSA-N 0.000 claims description 4
- AZLHFBQFMUUGQV-UHFFFAOYSA-N CC1=NC=C(C(=C1)NC1=NC(=NC=C1OC)C1=NN(C2=CC=CC=C12)CC1=C(C=C(OCCCO)C=C1F)F)C Chemical compound CC1=NC=C(C(=C1)NC1=NC(=NC=C1OC)C1=NN(C2=CC=CC=C12)CC1=C(C=C(OCCCO)C=C1F)F)C AZLHFBQFMUUGQV-UHFFFAOYSA-N 0.000 claims description 4
- KPMXRZRGKYONOC-UHFFFAOYSA-N CC1=NC=C(C(=C1)NC1=NC(=NC=C1OC)C1=NN(C2=CC=CC=C12)CC1=C(C=C(OCCO)C=C1F)F)C Chemical compound CC1=NC=C(C(=C1)NC1=NC(=NC=C1OC)C1=NN(C2=CC=CC=C12)CC1=C(C=C(OCCO)C=C1F)F)C KPMXRZRGKYONOC-UHFFFAOYSA-N 0.000 claims description 4
- XDDKFAVYRALFNW-UHFFFAOYSA-N ClC=1C=NC=CC=1NC1=NC(=NC=C1OC)C1=NN(C2=CC=CC=C12)CC1=C(C=C(OCCO)C=C1F)F Chemical compound ClC=1C=NC=CC=1NC1=NC(=NC=C1OC)C1=NN(C2=CC=CC=C12)CC1=C(C=C(OCCO)C=C1F)F XDDKFAVYRALFNW-UHFFFAOYSA-N 0.000 claims description 4
- OMOHVHZNCRENBT-UHFFFAOYSA-N FC(C1=NC=CC(=C1)NC1=NC(=NC=C1OC)C1=NN(C2=CC=CC=C12)CC1=C(C=C(OCCO)C=C1F)F)F Chemical compound FC(C1=NC=CC(=C1)NC1=NC(=NC=C1OC)C1=NN(C2=CC=CC=C12)CC1=C(C=C(OCCO)C=C1F)F)F OMOHVHZNCRENBT-UHFFFAOYSA-N 0.000 claims description 4
- HBVMURLVNVHXMZ-UHFFFAOYSA-N FC1=C(CN2N=C(C3=CC=CC=C23)C2=NC=C(C(=N2)NC2=CC(=NC=C2)NC(=O)C2CC2)OC)C(=CC(=C1)OCCO)F Chemical compound FC1=C(CN2N=C(C3=CC=CC=C23)C2=NC=C(C(=N2)NC2=CC(=NC=C2)NC(=O)C2CC2)OC)C(=CC(=C1)OCCO)F HBVMURLVNVHXMZ-UHFFFAOYSA-N 0.000 claims description 4
- BIOPPPLFVKPPSV-UHFFFAOYSA-N FC1=C(CN2N=C(C3=CC=CC=C23)C2=NC=C(C(=N2)NC2=CC(=NC=C2)NC(C)=O)OC)C(=CC(=C1)OCCO)F Chemical compound FC1=C(CN2N=C(C3=CC=CC=C23)C2=NC=C(C(=N2)NC2=CC(=NC=C2)NC(C)=O)OC)C(=CC(=C1)OCCO)F BIOPPPLFVKPPSV-UHFFFAOYSA-N 0.000 claims description 4
- UWLIGUMEWIWGJA-QGZVFWFLSA-N FC1=C(CN2N=C(C3=CC=CC=C23)C2=NC=C(C(=N2)NC2=CC(=NC=C2)NC(C)=O)OC)C(=CC(=C1)OC[C@@H](CO)C)F Chemical compound FC1=C(CN2N=C(C3=CC=CC=C23)C2=NC=C(C(=N2)NC2=CC(=NC=C2)NC(C)=O)OC)C(=CC(=C1)OC[C@@H](CO)C)F UWLIGUMEWIWGJA-QGZVFWFLSA-N 0.000 claims description 4
- UOKBKUUNTJIBQD-UHFFFAOYSA-N FC1=C(CN2N=C(C3=CC=CC=C23)C2=NC=C(C(=N2)NC2=CC(=NC=C2C)NC(C)=O)OC)C(=CC(=C1)OCCO)F Chemical compound FC1=C(CN2N=C(C3=CC=CC=C23)C2=NC=C(C(=N2)NC2=CC(=NC=C2C)NC(C)=O)OC)C(=CC(=C1)OCCO)F UOKBKUUNTJIBQD-UHFFFAOYSA-N 0.000 claims description 4
- VCBJXDQBPSBQFL-UHFFFAOYSA-N FC=1C=C(OCCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=CC(=NC=C1)C)OC)F Chemical compound FC=1C=C(OCCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=CC(=NC=C1)C)OC)F VCBJXDQBPSBQFL-UHFFFAOYSA-N 0.000 claims description 4
- QBBHMMJJLHOAIW-UHFFFAOYSA-N FC=1C=C(OCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=C(C(=NC=C1)C)OC)OC)F Chemical compound FC=1C=C(OCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=C(C(=NC=C1)C)OC)OC)F QBBHMMJJLHOAIW-UHFFFAOYSA-N 0.000 claims description 4
- HBSJPJQBIKFQFE-UHFFFAOYSA-N FC=1C=C(OCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=C(C=NC=C1)C)OC)F Chemical compound FC=1C=C(OCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=C(C=NC=C1)C)OC)F HBSJPJQBIKFQFE-UHFFFAOYSA-N 0.000 claims description 4
- XSLIKTXXGQQKBW-UHFFFAOYSA-N FC=1C=C(OCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=C(C=NC=C1)F)OC)F Chemical compound FC=1C=C(OCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=C(C=NC=C1)F)OC)F XSLIKTXXGQQKBW-UHFFFAOYSA-N 0.000 claims description 4
- QVOGVAVHOLLLAZ-UHFFFAOYSA-N FC=1C=C(OCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=C(C=NC=C1)OC)OC)F Chemical compound FC=1C=C(OCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=C(C=NC=C1)OC)OC)F QVOGVAVHOLLLAZ-UHFFFAOYSA-N 0.000 claims description 4
- QRTAVTWIFZNXQN-UHFFFAOYSA-N FC=1C=C(OCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=CC(=NC=C1)C)OC)F Chemical compound FC=1C=C(OCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=CC(=NC=C1)C)OC)F QRTAVTWIFZNXQN-UHFFFAOYSA-N 0.000 claims description 4
- PKWOFYLMAHSQFD-UHFFFAOYSA-N FC=1C=C(OCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=CC(=NC=C1)F)OC)F Chemical compound FC=1C=C(OCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=CC(=NC=C1)F)OC)F PKWOFYLMAHSQFD-UHFFFAOYSA-N 0.000 claims description 4
- ZVCMASALTKEJIQ-UHFFFAOYSA-N FC=1C=C(OCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=CC(=NC=C1F)C)OC)F Chemical compound FC=1C=C(OCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=CC(=NC=C1F)C)OC)F ZVCMASALTKEJIQ-UHFFFAOYSA-N 0.000 claims description 4
- LKFUFDBSWBGFIK-UHFFFAOYSA-N FC=1C=C(OCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=CC(=NC=C1OC)C)OC)F Chemical compound FC=1C=C(OCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=CC(=NC=C1OC)C)OC)F LKFUFDBSWBGFIK-UHFFFAOYSA-N 0.000 claims description 4
- MCXBYXIBJFCXFZ-UHFFFAOYSA-N FC=1C=C(OCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=NC=NC=C1)OC)F Chemical compound FC=1C=C(OCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=NC=NC=C1)OC)F MCXBYXIBJFCXFZ-UHFFFAOYSA-N 0.000 claims description 4
- OMSMPCPLTGNODX-QGZVFWFLSA-N CC1=NC=C(C(=C1)NC1=NC(=NC=C1OC)C1=NN(C2=CC=CC=C12)CC1=C(C=C(OC[C@@H](CO)C)C=C1F)F)C Chemical compound CC1=NC=C(C(=C1)NC1=NC(=NC=C1OC)C1=NN(C2=CC=CC=C12)CC1=C(C=C(OC[C@@H](CO)C)C=C1F)F)C OMSMPCPLTGNODX-QGZVFWFLSA-N 0.000 claims description 3
- CDAJKEBTLKBUSG-UHFFFAOYSA-N FC=1C=C(OCCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=C(C=NC=C1)OC)OC)F Chemical compound FC=1C=C(OCCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=C(C=NC=C1)OC)OC)F CDAJKEBTLKBUSG-UHFFFAOYSA-N 0.000 claims description 3
- SKYOCCGOJLUTJT-UHFFFAOYSA-N FC=1C=C(OCCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=NC(=NC=C1)C)OC)F Chemical compound FC=1C=C(OCCCO)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=NC(=NC=C1)C)OC)F SKYOCCGOJLUTJT-UHFFFAOYSA-N 0.000 claims description 3
- ROMZFKRTAGTNBL-MRXNPFEDSA-N FC=1C=C(OC[C@@H](CO)C)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=NC(=NC=C1)C)OC)F Chemical compound FC=1C=C(OC[C@@H](CO)C)C=C(C=1CN1N=C(C2=CC=CC=C12)C1=NC=C(C(=N1)NC1=NC(=NC=C1)C)OC)F ROMZFKRTAGTNBL-MRXNPFEDSA-N 0.000 claims description 3
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims 24
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 11
- 229910052801 chlorine Inorganic materials 0.000 claims 11
- 239000000460 chlorine Substances 0.000 claims 11
- 229910052731 fluorine Inorganic materials 0.000 claims 11
- 239000011737 fluorine Substances 0.000 claims 11
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 9
- 201000010099 disease Diseases 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 5
- 239000004472 Lysine Substances 0.000 claims 5
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 5
- 235000004279 alanine Nutrition 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 5
- 238000002360 preparation method Methods 0.000 claims 5
- PECYZEOJVXMISF-UHFFFAOYSA-N 3-aminoalanine Chemical compound [NH3+]CC(N)C([O-])=O PECYZEOJVXMISF-UHFFFAOYSA-N 0.000 claims 4
- 239000004471 Glycine Substances 0.000 claims 4
- IDIDJDIHTAOVLG-VKHMYHEASA-N S-methylcysteine Chemical compound CSC[C@H](N)C(O)=O IDIDJDIHTAOVLG-VKHMYHEASA-N 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 125000006677 (C1-C3) haloalkoxy group Chemical group 0.000 claims 3
- 125000006699 (C1-C3) hydroxyalkyl group Chemical group 0.000 claims 3
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 3
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 3
- 239000004475 Arginine Substances 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- SNDPXSYFESPGGJ-BYPYZUCNSA-N L-2-aminopentanoic acid Chemical compound CCC[C@H](N)C(O)=O SNDPXSYFESPGGJ-BYPYZUCNSA-N 0.000 claims 3
- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 claims 3
- SNDPXSYFESPGGJ-UHFFFAOYSA-N L-norVal-OH Natural products CCCC(N)C(O)=O SNDPXSYFESPGGJ-UHFFFAOYSA-N 0.000 claims 3
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 3
- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 claims 3
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 claims 3
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 230000003463 hyperproliferative effect Effects 0.000 claims 3
- 229960003104 ornithine Drugs 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 239000004474 valine Substances 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- UKAUYVFTDYCKQA-UHFFFAOYSA-N -2-Amino-4-hydroxybutanoic acid Natural products OC(=O)C(N)CCO UKAUYVFTDYCKQA-UHFFFAOYSA-N 0.000 claims 2
- OZDAOHVKBFBBMZ-UHFFFAOYSA-N 2-aminopentanedioic acid;hydrate Chemical compound O.OC(=O)C(N)CCC(O)=O OZDAOHVKBFBBMZ-UHFFFAOYSA-N 0.000 claims 2
- 125000003143 4-hydroxybenzyl group Chemical group [H]C([*])([H])C1=C([H])C([H])=C(O[H])C([H])=C1[H] 0.000 claims 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 2
- LCWXJXMHJVIJFK-UHFFFAOYSA-N Hydroxylysine Natural products NCC(O)CC(N)CC(O)=O LCWXJXMHJVIJFK-UHFFFAOYSA-N 0.000 claims 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 2
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 2
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 claims 2
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 claims 2
- UKAUYVFTDYCKQA-VKHMYHEASA-N L-homoserine Chemical compound OC(=O)[C@@H](N)CCO UKAUYVFTDYCKQA-VKHMYHEASA-N 0.000 claims 2
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 2
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 claims 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 2
- 206010027476 Metastases Diseases 0.000 claims 2
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- IDIDJDIHTAOVLG-UHFFFAOYSA-N S-methyl-L-cysteine Natural products CSCC(N)C(O)=O IDIDJDIHTAOVLG-UHFFFAOYSA-N 0.000 claims 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 2
- 239000004473 Threonine Substances 0.000 claims 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000006241 alcohol protecting group Chemical group 0.000 claims 2
- 239000002246 antineoplastic agent Substances 0.000 claims 2
- 235000009582 asparagine Nutrition 0.000 claims 2
- 229960001230 asparagine Drugs 0.000 claims 2
- 235000003704 aspartic acid Nutrition 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 2
- RGTXVXDNHPWPHH-UHFFFAOYSA-N butane-1,3-diamine Chemical compound CC(N)CCN RGTXVXDNHPWPHH-UHFFFAOYSA-N 0.000 claims 2
- 230000030833 cell death Effects 0.000 claims 2
- 235000013477 citrulline Nutrition 0.000 claims 2
- 229960002173 citrulline Drugs 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 235000018417 cysteine Nutrition 0.000 claims 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 2
- YSMODUONRAFBET-UHFFFAOYSA-N delta-DL-hydroxylysine Natural products NCC(O)CCC(N)C(O)=O YSMODUONRAFBET-UHFFFAOYSA-N 0.000 claims 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- YSMODUONRAFBET-UHNVWZDZSA-N erythro-5-hydroxy-L-lysine Chemical compound NC[C@H](O)CC[C@H](N)C(O)=O YSMODUONRAFBET-UHNVWZDZSA-N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 239000004220 glutamic acid Substances 0.000 claims 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- QJHBJHUKURJDLG-UHFFFAOYSA-N hydroxy-L-lysine Natural products NCCCCC(NO)C(O)=O QJHBJHUKURJDLG-UHFFFAOYSA-N 0.000 claims 2
- 230000006698 induction Effects 0.000 claims 2
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 2
- 229960000310 isoleucine Drugs 0.000 claims 2
- 229930182817 methionine Natural products 0.000 claims 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 1
- 239000007848 Bronsted acid Substances 0.000 claims 1
- 206010008342 Cervix carcinoma Diseases 0.000 claims 1
- 208000006105 Uterine Cervical Neoplasms Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 201000010881 cervical cancer Diseases 0.000 claims 1
- 230000000973 chemotherapeutic effect Effects 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 239000012351 deprotecting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 201000005787 hematologic cancer Diseases 0.000 claims 1
- 208000019691 hematopoietic and lymphoid cell neoplasm Diseases 0.000 claims 1
- 208000024200 hematopoietic and lymphoid system neoplasm Diseases 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 239000007858 starting material Substances 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 0 C*C(Nc1nc(-c2n[n](Cc(c(F)cc(O*(C)*(C)OC(C(*)NC(C(*)N*)=O)=O)c3)c3F)c3ccccc23)ncc1O*)=**=N*=C Chemical compound C*C(Nc1nc(-c2n[n](Cc(c(F)cc(O*(C)*(C)OC(C(*)NC(C(*)N*)=O)=O)c3)c3F)c3ccccc23)ncc1O*)=**=N*=C 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Substances CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N n-propyl alcohol Natural products CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14185604 | 2014-09-19 | ||
| EP14185604.7 | 2014-09-19 | ||
| EP15176903.1 | 2015-07-15 | ||
| EP15176903 | 2015-07-15 | ||
| PCT/EP2015/071340 WO2016042084A1 (en) | 2014-09-19 | 2015-09-17 | Benzyl substituted indazoles as bub1 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2017530962A JP2017530962A (ja) | 2017-10-19 |
| JP2017530962A5 true JP2017530962A5 (enExample) | 2018-10-25 |
| JP6664385B2 JP6664385B2 (ja) | 2020-03-13 |
Family
ID=54140475
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017514825A Expired - Fee Related JP6664385B2 (ja) | 2014-09-19 | 2015-09-17 | Ｂｕｂ１阻害薬としてのベンジル置換インダゾール類 |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US10350206B2 (enExample) |
| EP (1) | EP3194379A1 (enExample) |
| JP (1) | JP6664385B2 (enExample) |
| KR (1) | KR20170049604A (enExample) |
| CN (1) | CN107001331A (enExample) |
| AP (1) | AP2017009803A0 (enExample) |
| AU (1) | AU2015316796A1 (enExample) |
| BR (1) | BR112017005444A2 (enExample) |
| CA (1) | CA2961589A1 (enExample) |
| CL (1) | CL2017000654A1 (enExample) |
| CO (1) | CO2017002532A2 (enExample) |
| CR (1) | CR20170100A (enExample) |
| CU (1) | CU20170029A7 (enExample) |
| DO (1) | DOP2017000078A (enExample) |
| EA (1) | EA032401B1 (enExample) |
| EC (1) | ECSP17016797A (enExample) |
| IL (1) | IL251071A0 (enExample) |
| MA (1) | MA39484A (enExample) |
| MX (1) | MX2017003664A (enExample) |
| NI (1) | NI201700034A (enExample) |
| PE (1) | PE20170697A1 (enExample) |
| PH (1) | PH12017500509A1 (enExample) |
| SG (1) | SG11201702082VA (enExample) |
| TN (1) | TN2017000092A1 (enExample) |
| TW (1) | TW201615636A (enExample) |
| UY (1) | UY36311A (enExample) |
| WO (1) | WO2016042084A1 (enExample) |
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA111754C2 (uk) | 2011-10-06 | 2016-06-10 | Байєр Фарма Акцієнгезелльшафт | Заміщені бензиліндазоли для застосування як інгібіторів bub1-кінази для лікування гіперпроліферативних захворювань |
| US9611267B2 (en) | 2012-06-13 | 2017-04-04 | Incyte Holdings Corporation | Substituted tricyclic compounds as FGFR inhibitors |
| TWI649318B (zh) | 2013-04-19 | 2019-02-01 | 英塞特控股公司 | 作為ｆｇｆｒ抑制劑之雙環雜環 |
| CN105452237A (zh) | 2013-06-21 | 2016-03-30 | 拜耳制药股份公司 | 杂芳基取代的吡唑 |
| WO2014202590A1 (en) | 2013-06-21 | 2014-12-24 | Bayer Pharma Aktiengesellschaft | Substituted benzylpyrazoles |
| US9682974B2 (en) | 2013-10-30 | 2017-06-20 | Bayer Pharma Aktiengesellschaft | Heteroaryl substituted pyrazoles |
| PL3102568T3 (pl) | 2014-02-06 | 2019-01-31 | Heptares Therapeutics Limited | Bicykliczne związki aza w postaci agonistów receptorów muskarynowych m1 |
| US10428044B2 (en) | 2014-06-17 | 2019-10-01 | Bayer Pharma Aktiengesellschaft | 3-amino-1,5,6,7-tetrahydro-4H-indol-4-ones |
| CR20170100A (es) | 2014-09-19 | 2017-04-24 | Bayer Pharma Aktiengesellchaft | Indazoles sustituidos con bencilo como inhibidores bub1 |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| AU2016219822B2 (en) | 2015-02-20 | 2020-07-09 | Incyte Holdings Corporation | Bicyclic heterocycles as FGFR inhibitors |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| TWI808055B (zh) | 2016-05-11 | 2023-07-11 | 美商滬亞生物國際有限公司 | Hdac 抑制劑與 pd-1 抑制劑之組合治療 |
| TWI794171B (zh) | 2016-05-11 | 2023-03-01 | 美商滬亞生物國際有限公司 | Ｈｄａｃ抑制劑與ｐｄ-ｌ１抑制劑之組合治療 |
| WO2018122168A1 (en) | 2016-12-29 | 2018-07-05 | Bayer Pharma Aktiengesellschaft | Combinations of bub1 kinase and parp inhibitors |
| WO2018158175A1 (en) | 2017-02-28 | 2018-09-07 | Bayer Pharma Aktiengesellschaft | Combination of bub1 inhibitors |
| ES2924359T3 (es) | 2017-04-11 | 2022-10-06 | Sunshine Lake Pharma Co Ltd | Compuestos de indazol sustituidos con flúor y usos de los mismos |
| WO2018206547A1 (en) | 2017-05-12 | 2018-11-15 | Bayer Pharma Aktiengesellschaft | Combination of bub1 and atr inhibitors |
| WO2018215282A1 (en) | 2017-05-26 | 2018-11-29 | Bayer Pharma Aktiengesellschaft | Combination of bub1 and pi3k inhibitors |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| ES2991427T3 (es) | 2018-05-04 | 2024-12-03 | Incyte Corp | Formas sólidas de un inhibidor de FGFR y procedimientos para preparar las mismas |
| TW201946630A (zh) | 2018-05-04 | 2019-12-16 | 美商英塞特公司 | Fgfr抑制劑之鹽 |
| US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
| WO2021007269A1 (en) | 2019-07-09 | 2021-01-14 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| WO2021067374A1 (en) | 2019-10-01 | 2021-04-08 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| GEAP202415945A (en) | 2019-10-14 | 2024-04-25 | Incyte Corp | Bicyclic heterocycles as fgfr inhibitors |
| WO2021076728A1 (en) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| CA3163875A1 (en) | 2019-12-04 | 2021-06-10 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| AU2020395185A1 (en) | 2019-12-04 | 2022-06-02 | Incyte Corporation | Derivatives of an FGFR inhibitor |
| WO2021146424A1 (en) | 2020-01-15 | 2021-07-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| EP4323405A1 (en) | 2021-04-12 | 2024-02-21 | Incyte Corporation | Combination therapy comprising an fgfr inhibitor and a nectin-4 targeting agent |
| AR126101A1 (es) | 2021-06-09 | 2023-09-13 | Incyte Corp | Heterociclos tricíclicos como inhibidores de fgfr |
| CA3220274A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
Family Cites Families (51)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5011472A (en) | 1988-09-06 | 1991-04-30 | Brown University Research Foundation | Implantable delivery system for biological factors |
| US5470862A (en) | 1995-02-03 | 1995-11-28 | Ohmeda Pharmaceutical Products Division Inc. | Substituted pyrazolyl compounds and methods employing such compounds |
| ID22176A (id) | 1996-10-14 | 1999-09-09 | Bayer Ag | Turunan pirazola tersubstitusi-heterosiklilmetil yang baru |
| DE19834047A1 (de) | 1998-07-29 | 2000-02-03 | Bayer Ag | Substituierte Pyrazolderivate |
| DE19846514A1 (de) | 1998-10-09 | 2000-04-20 | Bayer Ag | Neue Heterocyclyl-methyl-substituierte Pyrazole |
| JP4286146B2 (ja) | 2001-12-18 | 2009-06-24 | メルク エンド カムパニー インコーポレーテッド | メタボトロピックグルタミン酸受容体−５のヘテロアリール置換ピラゾール系調節剤 |
| US7166293B2 (en) | 2002-03-29 | 2007-01-23 | Carlsbad Technology, Inc. | Angiogenesis inhibitors |
| BR0314196A (pt) | 2002-09-10 | 2005-07-26 | Scios Inc | Inibidores de tgf-beta |
| DE10244810A1 (de) | 2002-09-26 | 2004-04-08 | Bayer Ag | Neue Morpholin-überbrückte Indazolderivate |
| WO2007038613A2 (en) | 2005-09-26 | 2007-04-05 | The Regents Of The University Of California | Selective serine/threonine kinase inhibitors |
| CA2553513A1 (en) | 2004-01-22 | 2005-08-04 | Altana Pharma Ag | N-4-(6- (heteo) aryl-pyrimidin-4-ylaminophenyl) -bezenesulfonamides as kinase inhibitors |
| WO2007065010A2 (en) | 2005-12-02 | 2007-06-07 | Hif Bio, Inc. | Anti-angiogenesis compounds |
| DE102006043443A1 (de) | 2006-09-15 | 2008-03-27 | Bayer Healthcare Ag | Neue aza-bicyclische Verbindungen und ihre Verwendung |
| AU2008253311A1 (en) | 2007-05-18 | 2008-11-27 | Bayer Schering Pharma Aktiengesellshaft | Inhibitors of hypoxia inducible factor (HIF) useful for treating hyper-proliferative disorders and diseases associated with angiogenesis |
| JP2010111624A (ja) | 2008-11-06 | 2010-05-20 | Shionogi & Co Ltd | Ｔｔｋ阻害作用を有するインダゾール誘導体 |
| US8354399B2 (en) | 2008-12-18 | 2013-01-15 | Nerviano Medical Sciences S.R.L. | Substituted indazole derivatives active as kinase inhibitors |
| US20120232062A1 (en) | 2009-10-20 | 2012-09-13 | Eiger Biopharmaceuticals, Inc. | Azaindazoles to treat flaviviridae virus infection |
| HUE026778T2 (en) | 2009-11-27 | 2016-08-29 | Adverio Pharma Gmbh | Method for producing methyl- {4,6-diamino-2-[1-(2-fluorobenzyl) -1H-pyrazolo[3,4-b]pyridin-3-yl]-pyrimidin-5-yl}-methyl carbamate and its purification for its use as a pharmaceutical agent |
| US20130178475A1 (en) | 2010-03-17 | 2013-07-11 | Ironwood Pharmaceuticals, Inc. | sGC STIMULATORS |
| EP2560966B1 (en) | 2010-03-30 | 2021-01-06 | Verseon International Corporation | Multisubstituted aromatic compounds as inhibitors of thrombin |
| EA026692B1 (ru) | 2010-06-30 | 2017-05-31 | Айронвуд Фармасьютикелз, Инк. | Стимуляторы sgc |
| UA111754C2 (uk) | 2011-10-06 | 2016-06-10 | Байєр Фарма Акцієнгезелльшафт | Заміщені бензиліндазоли для застосування як інгібіторів bub1-кінази для лікування гіперпроліферативних захворювань |
| ES2638144T3 (es) | 2011-12-21 | 2017-10-18 | Bayer Intellectual Property Gmbh | Bencilpirazoles sustituidos |
| EP2797915B1 (en) | 2011-12-27 | 2016-07-13 | Ironwood Pharmaceuticals, Inc. | 2-benzyl-3-(oxazole/thiazole)-5-(pyrimidin-2-yl)-1(H)-pyrazole derivatives as stimulators of the soluble guanylate cyclase (sGC) for the treatment of e.g. hypertension or heart failure |
| WO2013167698A1 (en) | 2012-05-11 | 2013-11-14 | Bayer Pharma Aktiengesellschaft | Substituted cycloalkenopyrazoles as bub1 inhibitors for the treatment of cancer |
| WO2014047111A1 (en) | 2012-09-18 | 2014-03-27 | Ironwood Pharmaceuticals, Inc. | Sgc stimulators |
| CA2885645A1 (en) | 2012-09-19 | 2014-03-27 | Ironwood Pharmaceuticals, Inc. | Sgc stimulators |
| US9738610B2 (en) | 2012-09-24 | 2017-08-22 | Whitehead Institute For Biomedical Research | Indazole derivatives and uses thereof |
| US20160046604A1 (en) | 2013-03-21 | 2016-02-18 | Bayer Pharma Aktiengesellschaft | Heteroaryl substituted indazoles |
| EP2976334A1 (en) | 2013-03-21 | 2016-01-27 | Bayer Pharma Aktiengesellschaft | Diaminoheteroaryl substituted indazoles |
| CA2907592A1 (en) | 2013-03-21 | 2014-09-25 | Bayer Pharma Aktiengesellschaft | 3-heteroaryl substituted indazoles |
| CN105452242A (zh) | 2013-06-21 | 2016-03-30 | 拜耳制药股份公司 | 杂芳基取代的吡唑 |
| CA2916097A1 (en) | 2013-06-21 | 2014-12-24 | Bayer Pharma Aktiengesellschaft | Substituted benzylpyrazoles |
| WO2014202590A1 (en) | 2013-06-21 | 2014-12-24 | Bayer Pharma Aktiengesellschaft | Substituted benzylpyrazoles |
| JP2016522231A (ja) | 2013-06-21 | 2016-07-28 | バイエル ファーマ アクチエンゲゼルシャフト | ジアミノヘテロアリール置換ピラゾール類 |
| CN105452237A (zh) | 2013-06-21 | 2016-03-30 | 拜耳制药股份公司 | 杂芳基取代的吡唑 |
| US9682974B2 (en) | 2013-10-30 | 2017-06-20 | Bayer Pharma Aktiengesellschaft | Heteroaryl substituted pyrazoles |
| SG11201701915TA (en) | 2014-09-19 | 2017-04-27 | Glaxosmithkline Ip Dev Ltd | Novel soluble guanylate cyclase activators and their use |
| JP2017535514A (ja) | 2014-09-19 | 2017-11-30 | バイエル ファーマ アクチエンゲゼルシャフト | Ｂｕｂ１キナーゼ阻害薬としてのベンジル置換インダゾール類 |
| US20170275270A1 (en) | 2014-09-19 | 2017-09-28 | Bayer Pharma Aktiengesellschaft | Benzyl substituted indazoles |
| JP2017534576A (ja) | 2014-09-19 | 2017-11-24 | ネステク ソシエテ アノニム | コンパニオンアニマルにおけるα−アミラーゼ阻害物質でのがんの治療 |
| LT3194376T (lt) | 2014-09-19 | 2019-02-25 | Forma Therapeutics, Inc. | Piridin-2(1h)-ono chinolinono dariniai, kaip mutantinės izocitratdehidrogenazės inhibitoriai |
| WO2016042081A1 (en) | 2014-09-19 | 2016-03-24 | Bayer Pharma Aktiengesellschaft | Benzyl substituted indazoles as bub1 kinase inhibitors |
| CR20170100A (es) | 2014-09-19 | 2017-04-24 | Bayer Pharma Aktiengesellchaft | Indazoles sustituidos con bencilo como inhibidores bub1 |
| WO2017148995A1 (en) | 2016-03-04 | 2017-09-08 | Bayer Pharma Aktiengesellschaft | 1-(pyrimidin-2-yl)-1h-indazoles having bub1 kinase inhibiting activity |
| WO2017157992A1 (en) | 2016-03-18 | 2017-09-21 | Bayer Pharma Aktiengesellschaft | Annulated pyrazoles as bub1 kinase inhibitors for treating proliferative disorders |
| WO2017157991A1 (en) | 2016-03-18 | 2017-09-21 | Bayer Pharma Aktiengesellschaft | 1-alkyl-pyrazoles and -indazoles as bub1 inhibitors for the treatment of hyperproliferative diseases |
| WO2018122168A1 (en) | 2016-12-29 | 2018-07-05 | Bayer Pharma Aktiengesellschaft | Combinations of bub1 kinase and parp inhibitors |
| WO2018158175A1 (en) | 2017-02-28 | 2018-09-07 | Bayer Pharma Aktiengesellschaft | Combination of bub1 inhibitors |
| WO2018206547A1 (en) | 2017-05-12 | 2018-11-15 | Bayer Pharma Aktiengesellschaft | Combination of bub1 and atr inhibitors |
| WO2018215282A1 (en) | 2017-05-26 | 2018-11-29 | Bayer Pharma Aktiengesellschaft | Combination of bub1 and pi3k inhibitors |
-
2015
- 2015-09-17 CR CR20170100A patent/CR20170100A/es unknown
- 2015-09-17 US US15/512,494 patent/US10350206B2/en not_active Expired - Fee Related
- 2015-09-17 MX MX2017003664A patent/MX2017003664A/es unknown
- 2015-09-17 MA MA039484A patent/MA39484A/fr unknown
- 2015-09-17 TN TN2017000092A patent/TN2017000092A1/en unknown
- 2015-09-17 PE PE2017000480A patent/PE20170697A1/es unknown
- 2015-09-17 EP EP15763619.2A patent/EP3194379A1/en not_active Withdrawn
- 2015-09-17 KR KR1020177010425A patent/KR20170049604A/ko not_active Withdrawn
- 2015-09-17 CU CUP2017000029A patent/CU20170029A7/xx unknown
- 2015-09-17 JP JP2017514825A patent/JP6664385B2/ja not_active Expired - Fee Related
- 2015-09-17 AU AU2015316796A patent/AU2015316796A1/en not_active Abandoned
- 2015-09-17 CA CA2961589A patent/CA2961589A1/en not_active Abandoned
- 2015-09-17 BR BR112017005444A patent/BR112017005444A2/pt not_active IP Right Cessation
- 2015-09-17 CN CN201580062951.4A patent/CN107001331A/zh active Pending
- 2015-09-17 SG SG11201702082VA patent/SG11201702082VA/en unknown
- 2015-09-17 EA EA201790649A patent/EA032401B1/ru not_active IP Right Cessation
- 2015-09-17 AP AP2017009803A patent/AP2017009803A0/en unknown
- 2015-09-17 WO PCT/EP2015/071340 patent/WO2016042084A1/en not_active Ceased
- 2015-09-18 UY UY0001036311A patent/UY36311A/es not_active Application Discontinuation
- 2015-09-18 TW TW104131025A patent/TW201615636A/zh unknown
-
2017
- 2017-03-09 IL IL251071A patent/IL251071A0/en unknown
- 2017-03-16 PH PH12017500509A patent/PH12017500509A1/en unknown
- 2017-03-17 CL CL2017000654A patent/CL2017000654A1/es unknown
- 2017-03-17 NI NI201700034A patent/NI201700034A/es unknown
- 2017-03-17 DO DO2017000078A patent/DOP2017000078A/es unknown
- 2017-03-17 CO CONC2017/0002532A patent/CO2017002532A2/es unknown
- 2017-03-17 EC ECIEPI201716797A patent/ECSP17016797A/es unknown