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 (cg-RX-API-DMAC7.html) | 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)
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 |
| EP3495367B1 (en) | 2012-06-13 | 2020-09-30 | Incyte Holdings Corporation | Substituted tricyclic compounds as fgfr inhibitors |
| DK2986610T5 (en) | 2013-04-19 | 2018-12-10 | Incyte Holdings Corp | BICYCLIC HETEROCYCLES AS FGFR INHIBITORS |
| CA2916116A1 (en) | 2013-06-21 | 2014-12-24 | Bayer Pharma Aktiengesellschaft | Substituted benzylpyrazoles |
| ES2652305T3 (es) | 2013-06-21 | 2018-02-01 | Bayer Pharma Aktiengesellschaft | Pirazoles heteroaril sustituidos |
| US9682974B2 (en) | 2013-10-30 | 2017-06-20 | Bayer Pharma Aktiengesellschaft | Heteroaryl substituted pyrazoles |
| SMT202400446T1 (it) | 2014-02-06 | 2024-11-15 | Nxera Pharma Uk Ltd | Composti aza biciclici come agonisti del recettore muscarinico |
| TW201613886A (en) | 2014-06-17 | 2016-04-16 | Bayer Pharma AG | 3-amino-1,5,6,7-tetrahydro-4h-indol-4-ones |
| TN2017000092A1 (en) | 2014-09-19 | 2018-07-04 | Bayer Pharma AG | Benzyl substituted indazoles as bub1 inhibitors. |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| CR20170390A (es) | 2015-02-20 | 2017-10-23 | Incyte Holdings Corp | Heterociclos biciclicos como inhibidores de fgfr |
| 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 |
| CN108727340B (zh) | 2017-04-11 | 2020-12-29 | 广东东阳光药业有限公司 | 氟取代的吲唑类化合物及其用途 |
| WO2018206547A1 (en) | 2017-05-12 | 2018-11-15 | Bayer Pharma Aktiengesellschaft | Combination of bub1 and atr inhibitors |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| WO2018215282A1 (en) | 2017-05-26 | 2018-11-29 | Bayer Pharma Aktiengesellschaft | Combination of bub1 and pi3k inhibitors |
| CN112566912A (zh) | 2018-05-04 | 2021-03-26 | 因赛特公司 | Fgfr抑制剂的盐 |
| US11466004B2 (en) | 2018-05-04 | 2022-10-11 | Incyte Corporation | Solid forms of an FGFR inhibitor and processes for preparing the same |
| WO2020185532A1 (en) | 2019-03-08 | 2020-09-17 | Incyte Corporation | Methods of treating cancer with an fgfr inhibitor |
| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| US12122767B2 (en) | 2019-10-01 | 2024-10-22 | 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 |
| BR112022010664A2 (pt) | 2019-12-04 | 2022-08-16 | Incyte Corp | Derivados de um inibidor de fgfr |
| EP4069696A1 (en) | 2019-12-04 | 2022-10-12 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| US12012409B2 (en) | 2020-01-15 | 2024-06-18 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| TW202304459A (zh) | 2021-04-12 | 2023-02-01 | 美商英塞特公司 | 包含ｆｇｆｒ抑制劑及ｎｅｃｔｉｎ－４靶向劑之組合療法 |
| WO2022261159A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| JP2024522189A (ja) | 2021-06-09 | 2024-06-11 | インサイト・コーポレイション | Ｆｇｆｒ阻害剤としての三環式ヘテロ環 |
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 |
| CZ130999A3 (cs) | 1996-10-14 | 1999-07-14 | Bayer Aktiengesellschaft | Heterocyklylmethyl-substituované deriváty pyrazolu, způsob jejich výroby, farmaceutické prostředky tyto látky obsahující a jejich použití pro výrobu léčiv |
| 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 |
| WO2003051833A2 (en) | 2001-12-18 | 2003-06-26 | Merck & Co., Inc. | Heteroaryl substituted pyrazole modulators of metabotropic glutamate receptor-5 |
| US7166293B2 (en) | 2002-03-29 | 2007-01-23 | Carlsbad Technology, Inc. | Angiogenesis inhibitors |
| US20040132730A1 (en) | 2002-09-10 | 2004-07-08 | Jonathan Axon | Inhibitors of TGFbeta |
| DE10244810A1 (de) | 2002-09-26 | 2004-04-08 | Bayer Ag | Neue Morpholin-überbrückte Indazolderivate |
| US8748601B2 (en) | 2003-04-11 | 2014-06-10 | The Regents Of The University Of California | Selective serine/threonine kinase inhibitors |
| US20080242681A1 (en) | 2004-01-22 | 2008-10-02 | Altana Pharma Ag | N-4-(6-(Hetero)Aryl-Pyrimidin-4-Ylaminophenyl)-Benzenesulfonamides 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 |
| CN102666537A (zh) | 2009-10-20 | 2012-09-12 | 艾格尔生物制药股份有限公司 | 治疗黄病毒科病毒感染的氮杂吲唑 |
| CN102791707B (zh) | 2009-11-27 | 2014-10-29 | 拜耳知识产权有限责任公司 | {4,6-二氨基-2-[1-(2-氟苄基)-1h-吡唑并[3,4-b]吡啶-3-基]嘧啶-5-基}甲基氨基甲酸甲酯的制备方法以及为了将其用作药用活性成分的纯化方法 |
| US20130178475A1 (en) | 2010-03-17 | 2013-07-11 | Ironwood Pharmaceuticals, Inc. | sGC STIMULATORS |
| RU2639876C2 (ru) | 2010-03-30 | 2017-12-25 | Версеон Корпорейшн | Мультизамещенные ароматические соединения в качестве ингибиторов тромбина |
| DK2588465T3 (en) | 2010-06-30 | 2017-05-01 | Ironwood Pharmaceuticals Inc | SGC stimulators |
| UA111754C2 (uk) * | 2011-10-06 | 2016-06-10 | Байєр Фарма Акцієнгезелльшафт | Заміщені бензиліндазоли для застосування як інгібіторів bub1-кінази для лікування гіперпроліферативних захворювань |
| WO2013092512A1 (en) | 2011-12-21 | 2013-06-27 | Bayer Intellectual Property Gmbh | Substituted benzylpyrazoles |
| 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 |
| HK1207861A1 (en) | 2012-05-11 | 2016-02-12 | Bayer Pharma Aktiengesellschaft | Substituted cycloalkenopyrazoles as bub1 inhibitors for the treatment of cancer |
| US9309235B2 (en) | 2012-09-18 | 2016-04-12 | Ironwood Pharmaceuticals, Inc. | SGC stimulators |
| US9487508B2 (en) | 2012-09-19 | 2016-11-08 | Ironwood Pharmaceuticals, Inc. | SGC stimulators |
| US9738610B2 (en) | 2012-09-24 | 2017-08-22 | Whitehead Institute For Biomedical Research | Indazole derivatives and uses thereof |
| CA2907594A1 (en) | 2013-03-21 | 2014-09-25 | Bayer Pharma Aktiengesellschaft | Heteroaryl substituted indazoles |
| JP2016514718A (ja) | 2013-03-21 | 2016-05-23 | バイエル ファーマ アクチエンゲゼルシャフト | ３−ヘテロアリール置換インダゾール類 |
| HK1217324A1 (zh) | 2013-03-21 | 2017-01-06 | Bayer Pharma Aktiengesellschaft | 二氨基杂芳基取代的吲唑 |
| ES2652305T3 (es) | 2013-06-21 | 2018-02-01 | Bayer Pharma Aktiengesellschaft | Pirazoles heteroaril sustituidos |
| CN105473570A (zh) | 2013-06-21 | 2016-04-06 | 拜耳制药股份公司 | 二氨基杂芳基取代的吡唑 |
| EP3010911A1 (en) | 2013-06-21 | 2016-04-27 | Bayer Pharma Aktiengesellschaft | Heteroaryl substituted pyrazoles |
| WO2014202583A1 (en) | 2013-06-21 | 2014-12-24 | Bayer Pharma Aktiengesellschaft | Substituted benzylpyrazoles |
| CA2916116A1 (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 |
| WO2016042080A1 (en) | 2014-09-19 | 2016-03-24 | Bayer Pharma Aktiengesellschaft | Benzyl substituted indazoles as bub1 kinase inhibitors |
| CA2961586A1 (en) | 2014-09-19 | 2016-03-24 | Bayer Pharma Aktiengesellschaft | Benzyl substituted indazoles as bub1 kinase inhibitors |
| WO2016042536A1 (en) | 2014-09-19 | 2016-03-24 | Glaxosmithkline Intellectual Property Development Limited | Novel soluble guanylate cyclase activators and their use |
| TN2017000092A1 (en) | 2014-09-19 | 2018-07-04 | Bayer Pharma AG | Benzyl substituted indazoles as bub1 inhibitors. |
| US20160082058A1 (en) | 2014-09-19 | 2016-03-24 | Nestec Sa | Methods and formulations for treatment, reduction, and prevention of cancer in a companion animal and for the reduction of postprandial blood glucose in a companion animal |
| LT3194376T (lt) | 2014-09-19 | 2019-02-25 | Forma Therapeutics, Inc. | Piridin-2(1h)-ono chinolinono dariniai, kaip mutantinės izocitratdehidrogenazės inhibitoriai |
| CN107148420A (zh) | 2014-09-19 | 2017-09-08 | 拜耳制药股份公司 | 苄基取代的吲唑类化合物 |
| 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 TN TN2017000092A patent/TN2017000092A1/en unknown
- 2015-09-17 JP JP2017514825A patent/JP6664385B2/ja not_active Expired - Fee Related
- 2015-09-17 EA EA201790649A patent/EA032401B1/ru not_active IP Right Cessation
- 2015-09-17 AU AU2015316796A patent/AU2015316796A1/en not_active Abandoned
- 2015-09-17 WO PCT/EP2015/071340 patent/WO2016042084A1/en not_active Ceased
- 2015-09-17 BR BR112017005444A patent/BR112017005444A2/pt not_active IP Right Cessation
- 2015-09-17 SG SG11201702082VA patent/SG11201702082VA/en unknown
- 2015-09-17 CN CN201580062951.4A patent/CN107001331A/zh active Pending
- 2015-09-17 MX MX2017003664A patent/MX2017003664A/es unknown
- 2015-09-17 US US15/512,494 patent/US10350206B2/en not_active Expired - Fee Related
- 2015-09-17 CA CA2961589A patent/CA2961589A1/en not_active Abandoned
- 2015-09-17 EP EP15763619.2A patent/EP3194379A1/en not_active Withdrawn
- 2015-09-17 AP AP2017009803A patent/AP2017009803A0/en unknown
- 2015-09-17 CU CUP2017000029A patent/CU20170029A7/xx unknown
- 2015-09-17 KR KR1020177010425A patent/KR20170049604A/ko not_active Withdrawn
- 2015-09-17 CR CR20170100A patent/CR20170100A/es unknown
- 2015-09-17 PE PE2017000480A patent/PE20170697A1/es unknown
- 2015-09-17 MA MA039484A patent/MA39484A/fr unknown
- 2015-09-18 TW TW104131025A patent/TW201615636A/zh unknown
- 2015-09-18 UY UY0001036311A patent/UY36311A/es not_active Application Discontinuation
-
2017
- 2017-03-09 IL IL251071A patent/IL251071A0/en unknown
- 2017-03-16 PH PH12017500509A patent/PH12017500509A1/en unknown
- 2017-03-17 EC ECIEPI201716797A patent/ECSP17016797A/es 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