ZA200106340B - Quinazoline derivatives as angiogenesis inhibitors. - Google Patents
Quinazoline derivatives as angiogenesis inhibitors. Download PDFInfo
- Publication number
- ZA200106340B ZA200106340B ZA200106340A ZA200106340A ZA200106340B ZA 200106340 B ZA200106340 B ZA 200106340B ZA 200106340 A ZA200106340 A ZA 200106340A ZA 200106340 A ZA200106340 A ZA 200106340A ZA 200106340 B ZA200106340 B ZA 200106340B
- Authority
- ZA
- South Africa
- Prior art keywords
- alkyl
- yloxy
- quinazoline
- methoxy
- hydroxy
- Prior art date
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- 229940121369 angiogenesis inhibitor Drugs 0.000 title description 2
- 239000004037 angiogenesis inhibitor Substances 0.000 title description 2
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
- -1 halegeno and C Chemical group 0.000 claims description 581
- 125000000217 alkyl group Chemical group 0.000 claims description 542
- 229910052739 hydrogen Inorganic materials 0.000 claims description 148
- 239000001257 hydrogen Substances 0.000 claims description 148
- 125000001424 substituent group Chemical group 0.000 claims description 129
- 150000002431 hydrogen Chemical class 0.000 claims description 112
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 107
- 125000005843 halogen group Chemical group 0.000 claims description 100
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 94
- 125000000623 heterocyclic group Chemical group 0.000 claims description 86
- 229910052757 nitrogen Inorganic materials 0.000 claims description 73
- 125000004043 oxo group Chemical group O=* 0.000 claims description 70
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 62
- 125000005842 heteroatom Chemical group 0.000 claims description 61
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 59
- 229910052760 oxygen Inorganic materials 0.000 claims description 57
- 125000003386 piperidinyl group Chemical group 0.000 claims description 57
- 229910052717 sulfur Inorganic materials 0.000 claims description 57
- 125000002393 azetidinyl group Chemical group 0.000 claims description 56
- 125000004122 cyclic group Chemical group 0.000 claims description 52
- 150000001875 compounds Chemical class 0.000 claims description 50
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 50
- 125000005505 thiomorpholino group Chemical group 0.000 claims description 46
- 125000004193 piperazinyl group Chemical group 0.000 claims description 44
- 125000003282 alkyl amino group Chemical group 0.000 claims description 40
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 32
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 20
- 125000001153 fluoro group Chemical group F* 0.000 claims description 20
- 125000004848 alkoxyethyl group Chemical group 0.000 claims description 19
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 19
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 19
- 125000000304 alkynyl group Chemical group 0.000 claims description 18
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 14
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 150000001721 carbon Chemical group 0.000 claims description 12
- 125000001246 bromo group Chemical group Br* 0.000 claims description 10
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 10
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 9
- 230000008728 vascular permeability Effects 0.000 claims description 9
- 125000004849 alkoxymethyl group Chemical group 0.000 claims description 8
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 8
- 241001465754 Metazoa Species 0.000 claims description 7
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 7
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 7
- 125000001589 carboacyl group Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical group [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 6
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 241000282412 Homo Species 0.000 claims description 5
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 5
- 230000001772 anti-angiogenic effect Effects 0.000 claims description 5
- 230000001603 reducing effect Effects 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 3
- 150000001408 amides Chemical class 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 229940002612 prodrug Drugs 0.000 claims description 3
- 239000000651 prodrug Substances 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 150000003568 thioethers Chemical class 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims 46
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 8
- 238000006243 chemical reaction Methods 0.000 claims 5
- KYZNICPMZHBROC-UHFFFAOYSA-N 4-fluoro-1h-indol-5-ol Chemical compound OC1=CC=C2NC=CC2=C1F KYZNICPMZHBROC-UHFFFAOYSA-N 0.000 claims 2
- UMWRMOYYUHIPDT-UHFFFAOYSA-N 4-fluoro-2-methyl-1h-indol-5-ol Chemical compound OC1=CC=C2NC(C)=CC2=C1F UMWRMOYYUHIPDT-UHFFFAOYSA-N 0.000 claims 2
- XQJHCCZRXUOIGW-UHFFFAOYSA-N 6-fluoro-1h-indol-5-ol Chemical compound C1=C(F)C(O)=CC2=C1NC=C2 XQJHCCZRXUOIGW-UHFFFAOYSA-N 0.000 claims 2
- GCAVJDUGKMXYET-UHFFFAOYSA-N 6-fluoro-2-methyl-1h-indol-5-ol Chemical compound OC1=C(F)C=C2NC(C)=CC2=C1 GCAVJDUGKMXYET-UHFFFAOYSA-N 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- AJTCPFPFRHDRSS-QGZVFWFLSA-N (2r)-1-[4-(1h-indol-5-yloxy)-6-methoxyquinazolin-7-yl]oxy-3-morpholin-4-ylpropan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC=NC(OC=3C=C4C=CNC4=CC=3)=C2C=C1OC)N1CCOCC1 AJTCPFPFRHDRSS-QGZVFWFLSA-N 0.000 claims 1
- CAINZODQISJWSP-GOSISDBHSA-N (2r)-1-[4-(1h-indol-5-yloxy)-6-methoxyquinazolin-7-yl]oxy-3-piperidin-1-ylpropan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC=NC(OC=3C=C4C=CNC4=CC=3)=C2C=C1OC)N1CCCCC1 CAINZODQISJWSP-GOSISDBHSA-N 0.000 claims 1
- RGMVLDOREVSNEH-QGZVFWFLSA-N (2r)-1-[4-(1h-indol-5-yloxy)-6-methoxyquinazolin-7-yl]oxy-3-pyrrolidin-1-ylpropan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC=NC(OC=3C=C4C=CNC4=CC=3)=C2C=C1OC)N1CCCC1 RGMVLDOREVSNEH-QGZVFWFLSA-N 0.000 claims 1
- RMLKLTNSQXPRTB-GOSISDBHSA-N (2r)-1-[6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-pyrrolidin-1-ylpropan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC=NC(OC=3C=C4C=C(C)NC4=CC=3)=C2C=C1OC)N1CCCC1 RMLKLTNSQXPRTB-GOSISDBHSA-N 0.000 claims 1
- RCAIAVOQSMMUJK-GOSISDBHSA-N (2r)-1-[6-methoxy-4-[(3-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-piperidin-1-ylpropan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC=NC(OC=3C=C4C(C)=CNC4=CC=3)=C2C=C1OC)N1CCCCC1 RCAIAVOQSMMUJK-GOSISDBHSA-N 0.000 claims 1
- GAULSWVAQXWTPO-QGZVFWFLSA-N (2r)-1-[6-methoxy-4-[(3-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-pyrrolidin-1-ylpropan-2-ol Chemical compound C([C@@H](O)COC1=CC2=NC=NC(OC=3C=C4C(C)=CNC4=CC=3)=C2C=C1OC)N1CCCC1 GAULSWVAQXWTPO-QGZVFWFLSA-N 0.000 claims 1
- JEHHXBXKFYXWMT-OAHLLOKOSA-N (5r)-5-[[6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxymethyl]pyrrolidin-2-one Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OC[C@H]1CCC(=O)N1 JEHHXBXKFYXWMT-OAHLLOKOSA-N 0.000 claims 1
- YAWIAVFCBGTFIS-UHFFFAOYSA-N 1-(diethylamino)-3-[6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxypropan-2-ol Chemical compound C1=C2NC(C)=CC2=CC(OC=2N=CN=C3C=C(C(=CC3=2)OC)OCC(O)CN(CC)CC)=C1 YAWIAVFCBGTFIS-UHFFFAOYSA-N 0.000 claims 1
- BOYNTSOFXPSPNM-UHFFFAOYSA-N 1-[6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-(4-methylpiperazin-1-yl)propan-2-ol Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCC(O)CN1CCN(C)CC1 BOYNTSOFXPSPNM-UHFFFAOYSA-N 0.000 claims 1
- NCVLOJJBTMDBMS-UHFFFAOYSA-N 1-[6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-(propan-2-ylamino)propan-2-ol Chemical compound C1=C2NC(C)=CC2=CC(OC2=C3C=C(C(=CC3=NC=N2)OCC(O)CNC(C)C)OC)=C1 NCVLOJJBTMDBMS-UHFFFAOYSA-N 0.000 claims 1
- GFJOCFYAAVCNRB-UHFFFAOYSA-N 1-[6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-morpholin-4-ylpropan-2-ol Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCC(O)CN1CCOCC1 GFJOCFYAAVCNRB-UHFFFAOYSA-N 0.000 claims 1
- KGVZGCARCFJSCR-UHFFFAOYSA-N 1-[6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-piperidin-1-ylpropan-2-ol Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCC(O)CN1CCCCC1 KGVZGCARCFJSCR-UHFFFAOYSA-N 0.000 claims 1
- MYDKUTLLQONJKD-UHFFFAOYSA-N 2-[6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxy-n-methylethanamine Chemical compound C1=C2NC(C)=CC2=CC(OC=2N=CN=C3C=C(C(=CC3=2)OC)OCCNC)=C1 MYDKUTLLQONJKD-UHFFFAOYSA-N 0.000 claims 1
- QUTFAZLYDDGVLH-UHFFFAOYSA-N 3-[4-(1h-indol-5-yloxy)-6-methoxyquinazolin-7-yl]oxy-n,n-dimethylpropan-1-amine Chemical compound C1=C2NC=CC2=CC(OC2=C3C=C(C(=CC3=NC=N2)OCCCN(C)C)OC)=C1 QUTFAZLYDDGVLH-UHFFFAOYSA-N 0.000 claims 1
- APUJNJMMOVJBMQ-UHFFFAOYSA-N 3-[4-[(2,3-dimethyl-1h-indol-5-yl)oxy]-6-methoxyquinazolin-7-yl]oxy-n,n-dimethylpropan-1-amine Chemical compound C1=C2NC(C)=C(C)C2=CC(OC2=C3C=C(C(=CC3=NC=N2)OCCCN(C)C)OC)=C1 APUJNJMMOVJBMQ-UHFFFAOYSA-N 0.000 claims 1
- KSYZTLBEZNPWQB-UHFFFAOYSA-N 3-[4-[2-[6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxyethoxy]piperidin-1-yl]propanenitrile Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OCCOC1CCN(CCC#N)CC1 KSYZTLBEZNPWQB-UHFFFAOYSA-N 0.000 claims 1
- SSPGYVCKWTUTSX-UHFFFAOYSA-N 3-[6-methoxy-4-[(2-methyl-1h-indol-5-yl)oxy]quinazolin-7-yl]oxy-3-piperidin-4-ylpropanenitrile Chemical compound COC1=CC2=C(OC=3C=C4C=C(C)NC4=CC=3)N=CN=C2C=C1OC(CC#N)C1CCNCC1 SSPGYVCKWTUTSX-UHFFFAOYSA-N 0.000 claims 1
- ZHWIBBNQOOPMAE-UHFFFAOYSA-N 4-(1h-indol-5-yloxy)-6-methoxy-7-(2-piperidin-1-ylethoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCCN1CCCCC1 ZHWIBBNQOOPMAE-UHFFFAOYSA-N 0.000 claims 1
- MEBAXCQMZHDHLI-UHFFFAOYSA-N 4-(1h-indol-5-yloxy)-6-methoxy-7-(2-piperidin-2-ylethoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCCC1CCCCN1 MEBAXCQMZHDHLI-UHFFFAOYSA-N 0.000 claims 1
- IFQGZDCTCSXUNK-UHFFFAOYSA-N 4-(1h-indol-5-yloxy)-6-methoxy-7-(2-pyridin-4-yloxyethoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCCOC1=CC=NC=C1 IFQGZDCTCSXUNK-UHFFFAOYSA-N 0.000 claims 1
- YUHFKJWRLSLBBH-UHFFFAOYSA-N 4-(1h-indol-5-yloxy)-6-methoxy-7-(3-methylsulfonylpropoxy)quinazoline Chemical compound C1=C2NC=CC2=CC(OC2=C3C=C(C(=CC3=NC=N2)OCCCS(C)(=O)=O)OC)=C1 YUHFKJWRLSLBBH-UHFFFAOYSA-N 0.000 claims 1
- ZQARCLVLXXXKJF-UHFFFAOYSA-N 4-(1h-indol-5-yloxy)-6-methoxy-7-(3-piperidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCCCN1CCCCC1 ZQARCLVLXXXKJF-UHFFFAOYSA-N 0.000 claims 1
- JJFONHXJKBVBHW-UHFFFAOYSA-N 4-(1h-indol-5-yloxy)-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCCCN1CCCC1 JJFONHXJKBVBHW-UHFFFAOYSA-N 0.000 claims 1
- GHAQVSSERMFIOD-UHFFFAOYSA-N 4-(1h-indol-5-yloxy)-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C=CNC4=CC=3)N=CN=C2C=C1OCC1CCN(C)CC1 GHAQVSSERMFIOD-UHFFFAOYSA-N 0.000 claims 1
- FDGLZZQHPXHDGZ-UHFFFAOYSA-N 4-(1h-indol-5-yloxy)-6-methoxy-7-[2-(2-methoxyethoxy)ethoxy]quinazoline Chemical compound C1=C2NC=CC2=CC(OC=2N=CN=C3C=C(C(=CC3=2)OC)OCCOCCOC)=C1 FDGLZZQHPXHDGZ-UHFFFAOYSA-N 0.000 claims 1
- DQNUKKHSBRKMTN-UHFFFAOYSA-N 4-(1h-indol-6-yloxy)-6-methoxy-7-(3-piperidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4NC=CC4=CC=3)N=CN=C2C=C1OCCCN1CCCCC1 DQNUKKHSBRKMTN-UHFFFAOYSA-N 0.000 claims 1
- WEXBUAHOJKVQNZ-UHFFFAOYSA-N 4-(3-fluoroquinolin-7-yl)oxy-6-methoxy-7-(3-piperidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4N=CC(F)=CC4=CC=3)N=CN=C2C=C1OCCCN1CCCCC1 WEXBUAHOJKVQNZ-UHFFFAOYSA-N 0.000 claims 1
- XNENFRLEEFRRCB-UHFFFAOYSA-N 4-(3-fluoroquinolin-7-yl)oxy-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4N=CC(F)=CC4=CC=3)N=CN=C2C=C1OCCCN1CCCC1 XNENFRLEEFRRCB-UHFFFAOYSA-N 0.000 claims 1
- QXMBFDNIAYVLFK-UHFFFAOYSA-N 4-[(2,3-dimethyl-1h-indol-5-yl)oxy]-6-methoxy-7-(3-pyrrolidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C(C)=C(C)NC4=CC=3)N=CN=C2C=C1OCCCN1CCCC1 QXMBFDNIAYVLFK-UHFFFAOYSA-N 0.000 claims 1
- CPYOLRZYFGXJMZ-UHFFFAOYSA-N 4-[(2,3-dimethyl-1h-indol-5-yl)oxy]-6-methoxy-7-[(1-methylpiperidin-3-yl)methoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C(C)=C(C)NC4=CC=3)N=CN=C2C=C1OCC1CCCN(C)C1 CPYOLRZYFGXJMZ-UHFFFAOYSA-N 0.000 claims 1
- BYXRJZJEIZSEEJ-UHFFFAOYSA-N 4-[(2,3-dimethyl-1h-indol-5-yl)oxy]-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazoline Chemical compound COC1=CC2=C(OC=3C=C4C(C)=C(C)NC4=CC=3)N=CN=C2C=C1OCC1CCN(C)CC1 BYXRJZJEIZSEEJ-UHFFFAOYSA-N 0.000 claims 1
- SUANGBBIESOPQK-UHFFFAOYSA-N 4-[(2-methyl-1h-indol-5-yl)oxy]-7-(2-piperidin-1-ylethoxy)quinazoline Chemical compound C=1C=C2NC(C)=CC2=CC=1OC(C1=CC=2)=NC=NC1=CC=2OCCN1CCCCC1 SUANGBBIESOPQK-UHFFFAOYSA-N 0.000 claims 1
- VBYBNMXKSTZHGU-UHFFFAOYSA-N 4-[(2-methyl-1h-indol-5-yl)oxy]-7-(3-methylsulfonylpropoxy)quinazoline Chemical compound CS(=O)(=O)CCCOC1=CC=C2C(OC=3C=C4C=C(NC4=CC=3)C)=NC=NC2=C1 VBYBNMXKSTZHGU-UHFFFAOYSA-N 0.000 claims 1
- KFPBKESUJSJWGU-UHFFFAOYSA-N 4-[(2-methyl-1h-indol-5-yl)oxy]-7-(3-pyrrolidin-1-ylpropoxy)quinazoline Chemical compound C=1C=C2NC(C)=CC2=CC=1OC(C1=CC=2)=NC=NC1=CC=2OCCCN1CCCC1 KFPBKESUJSJWGU-UHFFFAOYSA-N 0.000 claims 1
- RATKYOYWLZOLNN-UHFFFAOYSA-N 4-[(2-methyl-1h-indol-5-yl)oxy]-7-(piperidin-4-ylmethoxy)quinazoline Chemical compound C=1C=C2NC(C)=CC2=CC=1OC(C1=CC=2)=NC=NC1=CC=2OCC1CCNCC1 RATKYOYWLZOLNN-UHFFFAOYSA-N 0.000 claims 1
- MKAMATMVKCLDIG-UHFFFAOYSA-N 4-[(2-methyl-1h-indol-5-yl)oxy]-7-[2-(1,2,4-triazol-1-yl)ethoxy]quinazoline Chemical compound C=1C=C2NC(C)=CC2=CC=1OC(C1=CC=2)=NC=NC1=CC=2OCCN1C=NC=N1 MKAMATMVKCLDIG-UHFFFAOYSA-N 0.000 claims 1
- LBHIBGICIXQVKN-UHFFFAOYSA-N 4-[(4-bromo-1h-indol-5-yl)oxy]-6-methoxy-7-(3-piperidin-1-ylpropoxy)quinazoline Chemical compound COC1=CC2=C(OC=3C(=C4C=CNC4=CC=3)Br)N=CN=C2C=C1OCCCN1CCCCC1 LBHIBGICIXQVKN-UHFFFAOYSA-N 0.000 claims 1
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
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Families Citing this family (315)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE482946T1 (de) * | 1999-02-10 | 2010-10-15 | Astrazeneca Ab | Chinazolinderivate als angiogenesehemmer und zwischenprodukte dafür |
AU769222B2 (en) | 1999-11-05 | 2004-01-22 | Genzyme Corporation | Quinazoline derivatives as VEGF inhibitors |
DE60112268T2 (de) | 2000-03-06 | 2006-05-24 | Astrazeneca Ab | Verwendung von quinazolinderivate als inhibitoren der angiogenese |
GB0008269D0 (en) * | 2000-04-05 | 2000-05-24 | Astrazeneca Ab | Combination chemotherapy |
UA73993C2 (uk) | 2000-06-06 | 2005-10-17 | Астразенека Аб | Хіназолінові похідні для лікування пухлин та фармацевтична композиція |
CZ2003486A3 (cs) * | 2000-08-21 | 2003-05-14 | Astrazeneca Ab | Chinazolinové deriváty, způsob jejich přípravy a farmaceutický prostředek, který je obsahuje |
EP1326860A1 (en) | 2000-10-13 | 2003-07-16 | AstraZeneca AB | Quinazoline derivatives |
WO2002030924A1 (en) | 2000-10-13 | 2002-04-18 | Astrazeneca Ab | Quinazoline derivatives with anti-tumour activity |
IL155447A0 (en) | 2000-10-20 | 2003-11-23 | Eisai Co Ltd | Nitrogenous aromatic ring compounds |
EP1330444B1 (en) | 2000-11-01 | 2011-03-23 | Millennium Pharmaceuticals, Inc. | Nitrogenous heterocyclic compounds and process for making them |
ES2556946T3 (es) | 2000-12-21 | 2016-01-21 | Novartis Ag | Pirimidinaminas como moduladores de la angiogénesis |
US6995162B2 (en) * | 2001-01-12 | 2006-02-07 | Amgen Inc. | Substituted alkylamine derivatives and methods of use |
US7102009B2 (en) | 2001-01-12 | 2006-09-05 | Amgen Inc. | Substituted amine derivatives and methods of use |
US6878714B2 (en) | 2001-01-12 | 2005-04-12 | Amgen Inc. | Substituted alkylamine derivatives and methods of use |
US7105682B2 (en) * | 2001-01-12 | 2006-09-12 | Amgen Inc. | Substituted amine derivatives and methods of use |
PE20021011A1 (es) * | 2001-03-23 | 2003-02-01 | Bayer Corp | Derivados quinazolinicos como inhibidores de la rho-quinasa |
DE60218138T2 (de) * | 2001-03-23 | 2007-09-20 | Bayer Pharmaceuticals Corp., West Haven | Rho-kinase inhibitoren |
JP4307843B2 (ja) * | 2001-04-19 | 2009-08-05 | アストラゼネカ アクチボラグ | キナゾリン誘導体 |
AU2002350105A1 (en) | 2001-06-21 | 2003-01-08 | Ariad Pharmaceuticals, Inc. | Novel quinazolines and uses thereof |
ES2272737T3 (es) * | 2001-07-16 | 2007-05-01 | Astrazeneca Ab | Derivados de quinolina y su uso como inhibidores de tirosina quinasas. |
GB0128109D0 (en) * | 2001-11-23 | 2002-01-16 | Astrazeneca Ab | Therapeutic use |
PL371486A1 (en) | 2002-02-01 | 2005-06-13 | Astrazeneca Ab | Quinazoline compounds |
WO2003066602A1 (fr) | 2002-02-06 | 2003-08-14 | Ube Industries, Ltd. | Procede relatif a l'elaboration d'un compose 4-aminoquinazoline |
US6924285B2 (en) | 2002-03-30 | 2005-08-02 | Boehringer Ingelheim Pharma Gmbh & Co. | Bicyclic heterocyclic compounds, pharmaceutical compositions containing these compounds, their use and process for preparing them |
AU2003281193A1 (en) * | 2002-07-09 | 2004-01-23 | Astrazeneca Ab | Quinazoline derivatives for use in the treatment of cancer |
EP1521747B1 (en) | 2002-07-15 | 2018-09-05 | Symphony Evolution, Inc. | Receptor-type kinase modulators and methods of use |
EP1548008A4 (en) | 2002-08-23 | 2008-08-06 | Kirin Pharma Kk | COMPOUND HAVING BETA-TRANSFORMING GROWTH FACTOR INHIBITORY ACTIVITY AND DRUG CONTAINING COMPOSITION |
DK1562955T3 (da) | 2002-11-04 | 2008-06-02 | Astrazeneca Ab | Quinazolinderivater som Src-tyrosinkinaseinhibitorer |
JPWO2004080462A1 (ja) | 2003-03-10 | 2006-06-08 | エーザイ株式会社 | c−Kitキナーゼ阻害剤 |
GB0309850D0 (en) | 2003-04-30 | 2003-06-04 | Astrazeneca Ab | Quinazoline derivatives |
GB0310401D0 (en) * | 2003-05-07 | 2003-06-11 | Astrazeneca Ab | Therapeutic agent |
GB0316127D0 (en) * | 2003-07-10 | 2003-08-13 | Astrazeneca Ab | Combination therapy |
GB0316123D0 (en) * | 2003-07-10 | 2003-08-13 | Astrazeneca Ab | Combination therapy |
GB0318423D0 (en) * | 2003-08-06 | 2003-09-10 | Astrazeneca Ab | Chemical compounds |
GB0318422D0 (en) | 2003-08-06 | 2003-09-10 | Astrazeneca Ab | Chemical compounds |
EP1660090B1 (en) * | 2003-08-14 | 2012-11-21 | Array Biopharma, Inc. | Quinazoline analogs as receptor tyrosine kinase inhibitors |
SI2392565T1 (sl) | 2003-09-26 | 2014-05-30 | Exelixis, Inc. | c-Met modulatorji in postopki uporabe |
EP1683785B1 (en) | 2003-11-11 | 2013-10-16 | Eisai R&D Management Co., Ltd. | Urea derivative and process for producing the same |
GB0328040D0 (en) * | 2003-12-03 | 2004-01-07 | Coleman Robert E | Pharmaceutical uses of bisphosphonates |
CA2551508C (en) | 2003-12-23 | 2011-08-09 | Pfizer Inc. | Novel quinoline derivatives |
GB0330002D0 (en) * | 2003-12-24 | 2004-01-28 | Astrazeneca Ab | Quinazoline derivatives |
CN1933839A (zh) * | 2004-01-23 | 2007-03-21 | 安进公司 | 化合物和使用方法 |
AU2005207946A1 (en) * | 2004-01-23 | 2005-08-11 | Amgen Inc. | Quinoline quinazoline pyridine and pyrimidine counds and their use in the treatment of inflammation angiogenesis and cancer |
GB0406445D0 (en) * | 2004-03-23 | 2004-04-28 | Astrazeneca Ab | Combination therapy |
GB0406446D0 (en) * | 2004-03-23 | 2004-04-28 | Astrazeneca Ab | Combination therapy |
BRPI0508959A (pt) * | 2004-03-23 | 2007-08-14 | Astrazeneca Ab | uso de azd2171 ou de um sal do mesmo farmaceuticamente aceitável, uso de sal maleato de azd2171 e oxaliplatina, composição farmacêutica, kit, e, método para a produção de um efeito antiangiogênico e/ou de redução da permeabilidade vascular em um animal de sangue quente |
US7880000B2 (en) | 2004-05-07 | 2011-02-01 | Amgen Inc. | Protein kinase modulators and method of use |
US8772269B2 (en) | 2004-09-13 | 2014-07-08 | Eisai R&D Management Co., Ltd. | Use of sulfonamide-including compounds in combination with angiogenesis inhibitors |
WO2006030941A1 (ja) | 2004-09-13 | 2006-03-23 | Eisai R & D Management Co., Ltd. | スルホンアミド含有化合物の血管新生阻害物質との併用 |
AU2005283422C1 (en) | 2004-09-17 | 2017-02-02 | Eisai R & D Management Co., Ltd. | Medicinal composition |
US7285569B2 (en) | 2004-09-24 | 2007-10-23 | Hoff Hoffmann-La Roche Inc. | Tricycles, their manufacture and use as pharmaceutical agents |
TW200624431A (en) | 2004-09-24 | 2006-07-16 | Hoffmann La Roche | Phthalazinone derivatives, their manufacture and use as pharmaceutical agents |
JP2008514576A (ja) * | 2004-09-27 | 2008-05-08 | アストラゼネカ アクチボラグ | Azd2171およびイマチニブを含む癌組合せ療法 |
EP1802591B1 (en) | 2004-10-12 | 2012-01-11 | AstraZeneca AB | Quinazoline derivatives |
CA2587642C (en) | 2004-11-30 | 2013-04-09 | Amgen Inc. | Substituted heterocycles and methods of use |
DK1838733T3 (da) | 2004-12-21 | 2011-11-28 | Medimmune Ltd | Antistoffer rettet mod angiopoietin-2 og anvendelser deraf |
EP1674467A1 (en) * | 2004-12-22 | 2006-06-28 | 4Sc Ag | 2,5- and 2,6-disubstituted benzazole derivatives useful as protein kinase inhibitors |
BRPI0608178A2 (pt) | 2005-04-14 | 2009-11-17 | Hoffmann La Roche | derivados de aminopirazol, sua fabricação, composição farmacêutica e uso como agentes farmacêuticos |
JO2787B1 (en) | 2005-04-27 | 2014-03-15 | امجين إنك, | Alternative amide derivatives and methods of use |
AU2006299902B2 (en) | 2005-05-18 | 2012-11-01 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
CA2611688A1 (en) | 2005-06-30 | 2007-01-11 | Amgen Inc. | Bis-aryl kinase inhibitors and their use in the treatment of inflammation, angiogenesis and cancer |
WO2007015569A1 (ja) * | 2005-08-01 | 2007-02-08 | Eisai R & D Management Co., Ltd. | 血管新生阻害物質の効果を予測する方法 |
EP2281901B1 (en) | 2005-08-02 | 2013-11-27 | Eisai R&D Management Co., Ltd. | Anti-tumour pharmaceutical composition with angiogenesis inhibitors |
CN101277720A (zh) * | 2005-09-01 | 2008-10-01 | 卫材R&D管理有限公司 | 崩解性被改善的药物组合物的制备方法 |
US8247556B2 (en) | 2005-10-21 | 2012-08-21 | Amgen Inc. | Method for preparing 6-substituted-7-aza-indoles |
CN101316590B (zh) * | 2005-11-07 | 2011-08-03 | 卫材R&D管理有限公司 | 血管生成抑制剂和c-kit激酶抑制剂的组合使用 |
WO2007061130A1 (ja) * | 2005-11-22 | 2007-05-31 | Eisai R & D Management Co., Ltd. | 多発性骨髄腫に対する抗腫瘍剤 |
GB0523810D0 (en) * | 2005-11-23 | 2006-01-04 | Astrazeneca Ab | Pharmaceutical compositions |
EP1965801B1 (en) * | 2005-12-22 | 2011-03-23 | AstraZeneca AB | Combination of azd2171 and pemetrexed |
US7868177B2 (en) | 2006-02-24 | 2011-01-11 | Amgen Inc. | Multi-cyclic compounds and method of use |
MX2008010953A (es) * | 2006-02-28 | 2008-09-08 | Amgen Inc | Derivados de cinolina y quinoxalina como inhibidores de la fosfodiesterasa 10. |
US20090076075A1 (en) * | 2006-03-02 | 2009-03-19 | Frederic Henri Jung | Quinoline derivatives |
UY30183A1 (es) * | 2006-03-02 | 2007-10-31 | Astrazeneca Ab | Derivados de quinolina |
TW200813091A (en) | 2006-04-10 | 2008-03-16 | Amgen Fremont Inc | Targeted binding agents directed to uPAR and uses thereof |
US20090209580A1 (en) * | 2006-05-18 | 2009-08-20 | Eisai R & D Management Co., Ltd. | Antitumor agent for thyroid cancer |
WO2008001956A1 (fr) * | 2006-06-29 | 2008-01-03 | Eisai R & D Management Co., Ltd. | Agent thérapeutique contre la fibrose hépatique |
CL2007002225A1 (es) | 2006-08-03 | 2008-04-18 | Astrazeneca Ab | Agente de union especifico para un receptor del factor de crecimiento derivado de plaquetas (pdgfr-alfa); molecula de acido nucleico que lo codifica; vector y celula huesped que la comprenden; conjugado que comprende al agente; y uso del agente de un |
MY148688A (en) | 2006-08-23 | 2013-05-31 | Kudos Pharm Ltd | 2-methylmorpholine pyrido-, pyrazo- and pyrimido-pyrimidine derivatives as mtor inhibitors |
JP5368096B2 (ja) | 2006-08-28 | 2013-12-18 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | 未分化型胃癌に対する抗腫瘍剤 |
CA2662587C (en) | 2006-09-11 | 2013-08-06 | Curis, Inc. | Quinazoline based egfr inhibitors |
US7851623B2 (en) | 2006-11-02 | 2010-12-14 | Astrazeneca Ab | Chemical process |
AU2012204077B2 (en) * | 2006-11-02 | 2012-11-29 | Astrazeneca Ab | Process for preparing indol-5-oxy-quinazoline derivatives and intermediates |
EP1921070A1 (de) | 2006-11-10 | 2008-05-14 | Boehringer Ingelheim Pharma GmbH & Co. KG | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstelllung |
US8338455B2 (en) | 2006-12-20 | 2012-12-25 | Amgen Inc. | Compounds and methods of use |
WO2008093855A1 (ja) | 2007-01-29 | 2008-08-07 | Eisai R & D Management Co., Ltd. | 未分化型胃癌治療用組成物 |
JP5377332B2 (ja) | 2007-02-06 | 2013-12-25 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 二環式へテロ環、それらの化合物を含む薬剤、その使用及びその製法 |
US20080190689A1 (en) * | 2007-02-12 | 2008-08-14 | Ballard Ebbin C | Inserts for engine exhaust systems |
US8148532B2 (en) | 2007-03-14 | 2012-04-03 | Guoqing Paul Chen | Spiro substituted compounds as angiogenesis inhibitors |
JPWO2008114819A1 (ja) | 2007-03-20 | 2010-07-08 | 大日本住友製薬株式会社 | 新規アデニン化合物 |
AR065784A1 (es) | 2007-03-20 | 2009-07-01 | Dainippon Sumitomo Pharma Co | Derivados de 8-oxo adenina,medicamentos que los contienen y usos como agentes terapeuticos para enfermedades alergicas, antivirales o antibacterianas. |
WO2008125820A1 (en) * | 2007-04-13 | 2008-10-23 | Astrazeneca Ab | Combination therapy comprising azd2171 and azd6244 or mek-inhibitor ii |
TWI484960B (zh) | 2007-04-16 | 2015-05-21 | Hutchison Medipharma Entpr Ltd | 嘧啶衍生物 |
WO2009030224A2 (de) * | 2007-09-07 | 2009-03-12 | Schebo Biotech Ag | Neue chinazolin- verbindungen und ihre verwendung zur therapie von krebserkrankungen |
EP2190287B1 (en) | 2007-09-10 | 2014-10-29 | Curis, Inc. | Tartrate salts or complexes of quinazoline based egfr inhibitors containing a zinc binding moiety |
TW200922590A (en) * | 2007-09-10 | 2009-06-01 | Curis Inc | VEGFR inhibitors containing a zinc binding moiety |
US8119616B2 (en) | 2007-09-10 | 2012-02-21 | Curis, Inc. | Formulation of quinazoline based EGFR inhibitors containing a zinc binding moiety |
KR101494734B1 (ko) | 2007-10-11 | 2015-02-26 | 아스트라제네카 아베 | 단백질 키나제 b 억제제로서 피롤로[2,3-d]피리미딘 유도체 |
MX2010004620A (es) * | 2007-10-29 | 2010-07-28 | Amgen Inc | Derivados de benzomorfolina y metodos de uso. |
KR101513326B1 (ko) | 2007-11-09 | 2015-04-17 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 혈관 신생 저해 물질과 항종양성 백금 착물의 병용 |
DK2222675T3 (da) | 2007-12-19 | 2013-11-04 | Genentech Inc | 5-anilinoimidazopyridiner og fremgangsmåder til deres anvendelse |
KR20100099185A (ko) | 2007-12-21 | 2010-09-10 | 제넨테크, 인크. | 아자인돌리진 및 이용 방법 |
CN101215274B (zh) * | 2007-12-27 | 2011-05-04 | 上海北卡医药技术有限公司 | N取代吗啉类有机化合物的制备工艺 |
EP2247579B1 (en) * | 2008-01-17 | 2012-04-18 | Bayer Pharma Aktiengesellschaft | Sulphoximine-substituted quinazoline derivatives as immunomodulators, their preparation and use as medicaments |
WO2009094211A1 (en) * | 2008-01-22 | 2009-07-30 | Concert Pharmaceuticals Inc. | Quinazoline compounds and methods of treating cancer |
US20100324087A1 (en) * | 2008-01-29 | 2010-12-23 | Eisai R&D Management Co., Ltd. | Combined use of angiogenesis inhibitor and taxane |
BRPI0907916A2 (pt) | 2008-02-07 | 2015-07-28 | Boehringer Ingelheim Int | Heterociclos espirociclos, medicamentos contendo esses compostos, e processos para preparar os mesmos |
WO2009104019A1 (en) * | 2008-02-21 | 2009-08-27 | Astrazeneca Ab | Combination therapy 238 |
BRPI0909082A2 (pt) * | 2008-03-26 | 2019-02-26 | Novartis Ag | imidazoquinolinas e derivados de pirimidina como moduladores potentes de processos angiogênicos acionados por vegf |
US7829574B2 (en) * | 2008-05-09 | 2010-11-09 | Hutchison Medipharma Enterprises Limited | Substituted quinazoline compounds and their use in treating angiogenesis-related diseases |
EP2303276B1 (en) | 2008-05-13 | 2013-11-13 | AstraZeneca AB | Fumarate salt of 4-(3-chloro-2-fluoroanilino)-7-methoxy-6-{[1-(n-methylcarbamoylmethyl)piperidin-4-yl]oxy}quinazoline |
US8426430B2 (en) | 2008-06-30 | 2013-04-23 | Hutchison Medipharma Enterprises Limited | Quinazoline derivatives |
EP2149565A1 (de) * | 2008-07-24 | 2010-02-03 | Bayer Schering Pharma AG | Sulfonsubstituierte Chinazolinderivate als Immunmodulatoren zur Behandlung von enzündlichen und allergischen Erkrankungen |
JP5539351B2 (ja) | 2008-08-08 | 2014-07-02 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | シクロヘキシルオキシ置換ヘテロ環、これらの化合物を含有する医薬、およびそれらを生成するための方法 |
US8211911B2 (en) | 2008-08-19 | 2012-07-03 | Guoqing Paul Chen | Compounds as kinase inhibitors |
TW201008933A (en) | 2008-08-29 | 2010-03-01 | Hutchison Medipharma Entpr Ltd | Pyrimidine compounds |
US8192738B2 (en) | 2008-09-19 | 2012-06-05 | Medimmune, Llc | Targeted antibodies directed to DLL4 |
RU2011119478A (ru) * | 2008-10-14 | 2012-11-27 | Нин Си | Соединения и способы применения |
UY32351A (es) | 2008-12-22 | 2010-07-30 | Astrazeneca Ab | Compuestos de pirimidinil indol para uso como inhibidores de atr |
US20120114667A1 (en) | 2008-12-23 | 2012-05-10 | Medimmune Limited | TARGETED BINDING AGENTS DIRECTED TO a5BETA1 AND USES THEREOF |
WO2010083414A1 (en) | 2009-01-16 | 2010-07-22 | Exelixis, Inc. | Malate salt of n- (4- { [ 6, 7-bis (methyloxy) quin0lin-4-yl] oxy}phenyl-n' - (4 -fluorophenyl) cyclopropane-1-dicarboxamide, and crystalline forms therof for the treatment of cancer |
WO2010091150A1 (en) | 2009-02-05 | 2010-08-12 | Immunogen, Inc. | Novel benzodiazepine derivatives |
WO2010089580A1 (en) | 2009-02-06 | 2010-08-12 | Astrazeneca Ab | Use of a mct1 inhibitor in the treatment of cancers expressing mct1 over mct4 |
PE20120603A1 (es) | 2009-02-10 | 2012-06-14 | Astrazeneca Ab | Derivados de triazolo[4,3-b]piridazina y sus usos para el cancer de prostata |
US8785457B2 (en) | 2009-03-13 | 2014-07-22 | Cellzome Limited | Pyrimidine derivatives as mTOR inhibitors |
IT1393351B1 (it) * | 2009-03-16 | 2012-04-20 | Eos Ethical Oncology Science Spa In Forma Abbreviata Eos Spa | Procedimento per la preparazione della 6-(7-((1-amminociclopropil)metossi)-6-metossichinolin-4-ilossi)-n-metil-1-naftammide e suoi intermedi di sintesi |
KR20110133048A (ko) * | 2009-03-21 | 2011-12-09 | 닝 시 | 아미노 에스테르 유도체, 그의 염 및 이용 방법 |
GB0905127D0 (en) | 2009-03-25 | 2009-05-06 | Pharminox Ltd | Novel prodrugs |
WO2010118986A1 (en) | 2009-04-14 | 2010-10-21 | Cellzome Limited | Fluoro substituted pyrimidine compounds as jak3 inhibitors |
US8389580B2 (en) | 2009-06-02 | 2013-03-05 | Duke University | Arylcyclopropylamines and methods of use |
US20100317593A1 (en) | 2009-06-12 | 2010-12-16 | Astrazeneca Ab | 2,3-dihydro-1h-indene compounds |
UA108618C2 (uk) | 2009-08-07 | 2015-05-25 | Застосування c-met-модуляторів в комбінації з темозоломідом та/або променевою терапією для лікування раку | |
WO2011029807A1 (en) | 2009-09-11 | 2011-03-17 | Cellzome Limited | Ortho substituted pyrimidine compounds as jak inhibitors |
US9242987B2 (en) | 2009-10-20 | 2016-01-26 | Cellzome Limited | Heterocyclyl pyrazolopyrimidine analogues as JAK inhibitors |
US8399460B2 (en) | 2009-10-27 | 2013-03-19 | Astrazeneca Ab | Chromenone derivatives |
AR079050A1 (es) | 2009-11-18 | 2011-12-21 | Astrazeneca Ab | Compuestos benzoimidazolicos y sus usos |
KR101934071B1 (ko) | 2009-11-24 | 2019-01-02 | 메디뮨 리미티드 | B7―h1에 대한 표적화된 결합 물질 |
EP2507237A1 (en) | 2009-12-03 | 2012-10-10 | Dainippon Sumitomo Pharma Co., Ltd. | Imidazoquinolines which act via toll - like receptors (tlr) |
AU2010343102B2 (en) * | 2009-12-29 | 2016-03-24 | Dana-Farber Cancer Institute, Inc. | Type II Raf kinase inhibitors |
ES2857626T3 (es) | 2010-01-15 | 2021-09-29 | Suzhou Neupharma Co Ltd | Ciertas entidades químicas, composiciones y métodos |
WO2011089416A1 (en) | 2010-01-19 | 2011-07-28 | Astrazeneca Ab | Pyrazine derivatives |
WO2011095807A1 (en) | 2010-02-07 | 2011-08-11 | Astrazeneca Ab | Combinations of mek and hh inhibitors |
WO2011100403A1 (en) | 2010-02-10 | 2011-08-18 | Immunogen, Inc | Cd20 antibodies and uses thereof |
ES2535116T3 (es) | 2010-03-04 | 2015-05-05 | Cellzome Limited | Derivados de urea sustituida con morfolino como inhibidores de mtor |
CN103180322A (zh) | 2010-04-30 | 2013-06-26 | 塞尔佐姆有限公司 | 作为jak抑制剂的吡唑化合物 |
SA111320519B1 (ar) | 2010-06-11 | 2014-07-02 | Astrazeneca Ab | مركبات بيريميدينيل للاستخدام كمثبطات atr |
ES2573515T3 (es) | 2010-06-25 | 2016-06-08 | Eisai R&D Management Co., Ltd. | Agente antitumoral que emplea compuestos con efecto inhibitorio de cinasas combinados |
EP2588105A1 (en) | 2010-07-01 | 2013-05-08 | Cellzome Limited | Triazolopyridines as tyk2 inhibitors |
TWI535712B (zh) | 2010-08-06 | 2016-06-01 | 阿斯特捷利康公司 | 化合物 |
US9040545B2 (en) | 2010-08-20 | 2015-05-26 | Cellzome Limited | Heterocyclyl pyrazolopyrimidine analogues as selective JAK inhibitors |
US9018197B2 (en) | 2010-08-28 | 2015-04-28 | Suzhou Neupharma Co. Ltd. | Tetradecahydro-1H-cyclopenta[a]phenanthrene compounds, compositions, and related methods of use |
GB201016442D0 (en) | 2010-09-30 | 2010-11-17 | Pharminox Ltd | Novel acridine derivatives |
WO2012062704A1 (en) | 2010-11-09 | 2012-05-18 | Cellzome Limited | Pyridine compounds and aza analogues thereof as tyk2 inhibitors |
WO2012066336A1 (en) | 2010-11-19 | 2012-05-24 | Astrazeneca Ab | Benzylamine compounds as toll -like receptor 7 agonists |
WO2012067268A1 (en) | 2010-11-19 | 2012-05-24 | Dainippon Sumitomo Pharma Co., Ltd. | Cyclic amide compounds and their use in the treatment of disease |
WO2012067269A1 (en) | 2010-11-19 | 2012-05-24 | Dainippon Sumitomo Pharma Co., Ltd. | Aminoalkoxyphenyl compounds and their use in the treatment of disease |
WO2012066335A1 (en) | 2010-11-19 | 2012-05-24 | Astrazeneca Ab | Phenol compounds als toll -like receptor 7 agonists |
EP2670763B1 (en) | 2011-02-02 | 2018-08-01 | Suzhou Neupharma Co., Ltd | Certain chemical entities, compositions, and methods |
EP3053600B1 (en) | 2011-02-15 | 2020-01-29 | ImmunoGen, Inc. | Cytotoxic benzodiazepine derivatives |
WO2012110773A1 (en) | 2011-02-17 | 2012-08-23 | Cancer Therapeutics Crc Pty Limited | Fak inhibitors |
WO2012110774A1 (en) | 2011-02-17 | 2012-08-23 | Cancer Therapeutics Crc Pty Limited | Selective fak inhibitors |
GB201104267D0 (en) | 2011-03-14 | 2011-04-27 | Cancer Rec Tech Ltd | Pyrrolopyridineamino derivatives |
EP2694511A1 (en) | 2011-04-04 | 2014-02-12 | Cellzome Limited | Dihydropyrrolo pyrimidine derivatives as mtor inhibitors |
UY34013A (es) | 2011-04-13 | 2012-11-30 | Astrazeneca Ab | ?compuestos de cromenona con actividad anti-tumoral?. |
CN103402519B (zh) | 2011-04-18 | 2015-11-25 | 卫材R&D管理有限公司 | 肿瘤治疗剂 |
WO2012143320A1 (en) | 2011-04-18 | 2012-10-26 | Cellzome Limited | (7h-pyrrolo[2,3-d]pyrimidin-2-yl)amine compounds as jak3 inhibitors |
WO2012166899A2 (en) | 2011-06-03 | 2012-12-06 | Eisai R&D Management Co., Ltd. | Biomarkers for predicting and assessing responsiveness of thyroid and kidney cancer subjects to lenvatinib compounds |
WO2012175991A1 (en) | 2011-06-24 | 2012-12-27 | Pharminox Limited | Fused pentacyclic anti - proliferative compounds |
WO2013014448A1 (en) | 2011-07-27 | 2013-01-31 | Astrazeneca Ab | 2 - (2, 4, 5 - substituted -anilino) pyrimidine derivatives as egfr modulators useful for treating cancer |
US20140179664A1 (en) | 2011-07-28 | 2014-06-26 | Cellzome Limited | Heterocyclyl Pyrimidine Analogues As JAK Inhibitors |
WO2013017480A1 (en) | 2011-07-29 | 2013-02-07 | Cellzome Limited | Pyrazolo[4,3-c]pyridine derivatives as jak inhibitors |
WO2013017479A1 (en) | 2011-07-29 | 2013-02-07 | Cellzome Limited | Pyrazolo[4,3-c]pyridine derivatives as jak inhibitors |
CN104053442B (zh) | 2011-08-26 | 2017-06-23 | 润新生物公司 | 某些化学实体、组合物及方法 |
WO2013033250A1 (en) | 2011-09-01 | 2013-03-07 | Xiangping Qian | Certain chemical entities, compositions, and methods |
CN115403531A (zh) | 2011-09-14 | 2022-11-29 | 润新生物公司 | 作为激酶抑制剂的化学实体、组合物及方法 |
CA2849340A1 (en) | 2011-09-20 | 2013-03-28 | Cellzome Limited | Pyrazolo[4,3-c]pyridine derivatives as kinase inhibitors |
CN103917530B (zh) | 2011-09-21 | 2016-08-24 | 塞尔佐姆有限公司 | 作为mtor抑制剂的吗啉代取代的脲或氨基甲酸衍生物 |
WO2013043935A1 (en) | 2011-09-21 | 2013-03-28 | Neupharma, Inc. | Certain chemical entites, compositions, and methods |
EP2760458B1 (en) | 2011-09-29 | 2017-06-14 | The University of Liverpool | Prevention and/or treatment of cancer and/or cancer metastasis |
US9249111B2 (en) | 2011-09-30 | 2016-02-02 | Neupharma, Inc. | Substituted quinoxalines as B-RAF kinase inhibitors |
AU2012320465B2 (en) | 2011-10-07 | 2016-03-03 | Cellzome Limited | Morpholino substituted bicyclic pyrimidine urea or carbamate derivatives as mTOR inhibitors |
US20130178520A1 (en) | 2011-12-23 | 2013-07-11 | Duke University | Methods of treatment using arylcyclopropylamine compounds |
AU2012357038B2 (en) | 2011-12-23 | 2016-05-12 | Cellzome Limited | Pyrimidine-2,4-diamine derivatives as kinase inhibitors |
EP2806874B1 (en) | 2012-01-25 | 2017-11-15 | Neupharma, Inc. | Quinoxaline-oxy-phenyl derivatives as kinase inhibitors |
EP2626066A1 (en) | 2012-02-10 | 2013-08-14 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Combination therapy comprising selective VEGFR-2 inhibitors and MEK inhibitors |
WO2013165924A1 (en) | 2012-04-29 | 2013-11-07 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
SI2859017T1 (sl) | 2012-06-08 | 2019-05-31 | Sutro Biopharma, Inc. | Protitelesa, ki vsebujejo specifične nenaravne aminokislinske ostanke, postopki njihove priprave in postopki njihove uporabe |
EP3135690A1 (en) | 2012-06-26 | 2017-03-01 | Sutro Biopharma, Inc. | Modified fc proteins comprising site-specific non-natural amino acid residues, conjugates of the same, methods of their preparation and methods of their use |
US20160009686A1 (en) | 2012-08-17 | 2016-01-14 | Cancer Therapeutics Crc Pty Limited | Vegfr3 inhibitors |
EP2887965A1 (en) | 2012-08-22 | 2015-07-01 | ImmunoGen, Inc. | Cytotoxic benzodiazepine derivatives |
PL3584255T3 (pl) | 2012-08-31 | 2022-05-16 | Sutro Biopharma, Inc. | Modyfikowane aminokwasy zawierające grupę azydkową |
WO2014041349A1 (en) | 2012-09-12 | 2014-03-20 | Cancer Therapeutics Crc Pty Ltd | Tetrahydropyran-4-ylethylamino- or tetrahydropyranyl-4-ethyloxy-pyrimidines or -pyridazines as isoprenylcysteincarboxymethyl transferase inhibitors |
WO2014045101A1 (en) | 2012-09-21 | 2014-03-27 | Cellzome Gmbh | Tetrazolo quinoxaline derivatives as tankyrase inhibitors |
WO2014047648A1 (en) | 2012-09-24 | 2014-03-27 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
CN104955459B (zh) | 2012-11-05 | 2019-02-01 | 南特知识产权控股有限责任公司 | 取代的吲哚-5-酚衍生物及其治疗应用 |
US9725421B2 (en) | 2012-11-12 | 2017-08-08 | Neupharma, Inc. | Substituted quinoxalines as B-raf kinase inhibitors |
KR20150098605A (ko) | 2012-12-21 | 2015-08-28 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 퀴놀린 유도체의 비정질 형태 및 그의 제조방법 |
EP2951177B1 (en) | 2013-01-31 | 2018-04-04 | Neomed Institute | Imidazopyridine compounds and uses thereof |
WO2014127214A1 (en) | 2013-02-15 | 2014-08-21 | Kala Pharmaceuticals, Inc. | Therapeutic compounds and uses thereof |
CA2900680C (en) * | 2013-02-20 | 2021-08-10 | Kala Pharmaceuticals, Inc. | Quinoline and quinazoline compounds and uses thereof for treating and/or preventing diseases |
US9688688B2 (en) | 2013-02-20 | 2017-06-27 | Kala Pharmaceuticals, Inc. | Crystalline forms of 4-((4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-yl)oxy)-1-(2-oxa-7-azaspiro[3.5]nonan-7-yl)butan-1-one and uses thereof |
JP6423804B2 (ja) | 2013-02-28 | 2018-11-14 | イミュノジェン・インコーポレーテッド | 細胞結合剤及び細胞毒性剤を含む複合体 |
JP6494533B2 (ja) | 2013-02-28 | 2019-04-03 | イミュノジェン・インコーポレーテッド | 細胞結合剤及び細胞毒性剤としてのマイタンシノイドを含む複合体 |
PE20191685A1 (es) | 2013-03-13 | 2019-11-19 | Abbvie Inc | Procesos para la preparacion de un agente inductor de la apoptosis |
RU2015143657A (ru) | 2013-03-15 | 2017-04-27 | Нэнтбайосайенс, Инк. | Замещенные производные индол-5-ола и их терапевтические применения |
AR095443A1 (es) | 2013-03-15 | 2015-10-14 | Fundación Centro Nac De Investig Oncológicas Carlos Iii | Heterociclos condensados con acción sobre atr |
CN105142648A (zh) | 2013-03-15 | 2015-12-09 | 玛格塞蒂克斯公司 | 用于癌症的镁组合物及其用途 |
US9540381B2 (en) * | 2013-04-09 | 2017-01-10 | Guangzhou Kangrui Biological Pharmaceutical Technology Co., Ltd. | Anti-angiogenesis compound, intermediate and use thereof |
CA2912219C (en) | 2013-05-14 | 2021-11-16 | Eisai R&D Management Co., Ltd. | Biomarkers for predicting and assessing responsiveness of endometrial cancer subjects to lenvatinib compounds |
EP2806480B1 (en) * | 2013-05-20 | 2017-08-09 | Nintendo Co., Ltd. | Battery accomodation structure and battery accomodation method |
CN103275069B (zh) * | 2013-05-22 | 2015-03-11 | 苏州明锐医药科技有限公司 | 西地尼布的制备方法 |
WO2014194030A2 (en) | 2013-05-31 | 2014-12-04 | Immunogen, Inc. | Conjugates comprising cell-binding agents and cytotoxic agents |
EP3004073A1 (en) | 2013-06-07 | 2016-04-13 | Université catholique de Louvain | 3-carboxy substituted coumarin derivatives with a potential utility for the treatment of cancer diseases |
US9764039B2 (en) | 2013-07-10 | 2017-09-19 | Sutro Biopharma, Inc. | Antibodies comprising multiple site-specific non-natural amino acid residues, methods of their preparation and methods of their use |
JP6559132B2 (ja) | 2013-08-23 | 2019-08-14 | ニューファーマ, インコーポレイテッド | ある特定の化学的実体、組成物および方法 |
CN103509005B (zh) * | 2013-09-26 | 2015-04-08 | 苏州海特比奥生物技术有限公司 | 喹唑啉类化合物及其制备方法与应用 |
US9840493B2 (en) | 2013-10-11 | 2017-12-12 | Sutro Biopharma, Inc. | Modified amino acids comprising tetrazine functional groups, methods of preparation, and methods of their use |
EP2868702A1 (en) | 2013-10-29 | 2015-05-06 | DyStar Colours Distribution GmbH | Disperse dyes, their preparation and their use |
JP6426194B2 (ja) | 2013-11-01 | 2018-11-21 | カラ ファーマシューティカルズ インコーポレイテッド | 治療用化合物の結晶形態及びその使用 |
JP6426195B2 (ja) * | 2013-11-01 | 2018-11-21 | カラ ファーマシューティカルズ インコーポレイテッド | 治療用化合物の結晶形態及びその使用 |
US9890173B2 (en) | 2013-11-01 | 2018-02-13 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
GB201403536D0 (en) | 2014-02-28 | 2014-04-16 | Cancer Rec Tech Ltd | Inhibitor compounds |
KR102512940B1 (ko) | 2014-08-28 | 2023-03-23 | 에자이 알앤드디 매니지먼트 가부시키가이샤 | 고순도의 퀴놀린 유도체 및 이를 제조하는 방법 |
CN105461698A (zh) * | 2014-09-12 | 2016-04-06 | 杭州普晒医药科技有限公司 | 西地尼布盐及其晶型、以及其制备方法和药物组合物 |
MA41179A (fr) | 2014-12-19 | 2017-10-24 | Cancer Research Tech Ltd | Composés inhibiteurs de parg |
GB201501870D0 (en) | 2015-02-04 | 2015-03-18 | Cancer Rec Tech Ltd | Autotaxin inhibitors |
GB201502020D0 (en) | 2015-02-06 | 2015-03-25 | Cancer Rec Tech Ltd | Autotaxin inhibitory compounds |
WO2016133935A1 (en) | 2015-02-17 | 2016-08-25 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
JP6792546B2 (ja) | 2015-02-25 | 2020-11-25 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | キノリン誘導体の苦味抑制方法 |
WO2016140717A1 (en) | 2015-03-04 | 2016-09-09 | Merck Sharp & Dohme Corp. | Combination of a pd-1 antagonist and a vegfr/fgfr/ret tyrosine kinase inhibitor for treating cancer |
GB201510019D0 (en) | 2015-06-09 | 2015-07-22 | Cancer Therapeutics Crc Pty Ltd | Compounds |
US11369623B2 (en) | 2015-06-16 | 2022-06-28 | Prism Pharma Co., Ltd. | Anticancer combination of a CBP/catenin inhibitor and an immune checkpoint inhibitor |
CN108349964B (zh) | 2015-08-04 | 2021-06-01 | 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 |
CA3000988A1 (en) | 2015-10-05 | 2017-04-13 | The Trustees Of Columbia University In The City Of New York | Activators of autophagic flux and phospholipase d and clearance of protein aggregates including tau and treatment of proteinopathies |
SG11201806419RA (en) | 2016-01-27 | 2018-08-30 | Sutro Biopharma Inc | Anti-cd74 antibody conjugates, compositions comprising anti-cd74 antibody conjugates and methods of using anti-cd74 antibody conjugates |
AU2017221268B2 (en) | 2016-02-15 | 2024-02-15 | Astrazeneca Ab | Methods comprising fixed intermittent dosing of cediranib |
RS63609B1 (sr) | 2016-04-15 | 2022-10-31 | Cancer Research Tech Ltd | Heterociklična jedinjenja kao inhibitori ret kinaze |
GB2554333A (en) | 2016-04-26 | 2018-04-04 | Big Dna Ltd | Combination therapy |
CA3033370A1 (en) | 2016-08-15 | 2018-02-22 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
EP3507305A1 (en) | 2016-09-02 | 2019-07-10 | Dana-Farber Cancer Institute, Inc. | Composition and methods of treating b cell disorders |
JP2019533641A (ja) | 2016-09-08 | 2019-11-21 | カラ ファーマシューティカルズ インコーポレイテッド | 治療用化合物の結晶形態およびその使用 |
AU2017324713B2 (en) | 2016-09-08 | 2020-08-13 | KALA BIO, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
AU2017324716B2 (en) | 2016-09-08 | 2020-08-13 | KALA BIO, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
CA3037605A1 (en) | 2016-09-22 | 2018-03-29 | Cancer Research Technology Limited | Preparation and uses of pyrimidinone derivatives |
GB201617103D0 (en) | 2016-10-07 | 2016-11-23 | Cancer Research Technology Limited | Compound |
JP6755775B2 (ja) * | 2016-11-04 | 2020-09-16 | 富士アミドケミカル株式会社 | 4−フルオロイソキノリンの製法 |
CA3041563C (en) | 2016-11-22 | 2023-10-31 | Dana-Farber Cancer Institute, Inc. | Pyrimidin-2-amine derivatives and pharmaceutical compositions thereof useful as inhibitors of cyclin-dependent kinase 12 (cdk12) |
US10786502B2 (en) | 2016-12-05 | 2020-09-29 | Apros Therapeutics, Inc. | Substituted pyrimidines containing acidic groups as TLR7 modulators |
AU2017372722B2 (en) | 2016-12-05 | 2021-09-09 | Apros Therapeutics, Inc. | Pyrimidine compounds containing acidic groups |
CN106831729A (zh) * | 2016-12-19 | 2017-06-13 | 浙江工业大学 | 一种西地尼布的纯化方法 |
CA3051604A1 (en) | 2017-02-01 | 2018-08-09 | Aucentra Therapeutics Pty Ltd | Derivatives of n-cycloalkyl/heterocycloalkyl-4-(imidazo [1,2-a]pyridine)pyrimidin-2-amine as therapeutic agents |
GB201704325D0 (en) | 2017-03-17 | 2017-05-03 | Argonaut Therapeutics Ltd | Compounds |
GB201705971D0 (en) | 2017-04-13 | 2017-05-31 | Cancer Res Tech Ltd | Inhibitor compounds |
CN108864079B (zh) | 2017-05-15 | 2021-04-09 | 深圳福沃药业有限公司 | 一种三嗪化合物及其药学上可接受的盐 |
US11161839B2 (en) | 2017-05-26 | 2021-11-02 | The Institute Of Cancer Research: Royal Cancer Hospital | 2-quinolone derived inhibitors of BCL6 |
US20200207859A1 (en) | 2017-07-26 | 2020-07-02 | Sutro Biopharma, Inc. | Methods of using anti-cd74 antibodies and antibody conjugates in treatment of t-cell lymphoma |
US11447505B1 (en) | 2017-08-18 | 2022-09-20 | Cancer Research Technology Limited | Pyrrolo[2,3-b]pyridine compounds and their use in the treatment of cancer |
EP3684814A1 (en) | 2017-09-18 | 2020-07-29 | Sutro Biopharma, Inc. | Anti-folate receptor alpha antibody conjugates and their uses |
EP3697775A1 (en) * | 2017-10-20 | 2020-08-26 | Kala Pharmaceuticals, Inc. | Ret9 and vegfr2 inhibitors |
NL2019801B1 (en) | 2017-10-25 | 2019-05-02 | Univ Leiden | Delivery vectors |
EP3740484A4 (en) | 2018-01-15 | 2021-06-09 | Aucentra Holdings Pty Ltd | 5- (PYRIMIDIN-4-YL) THIAZOL-2-YL-UREA DERIVATIVES AS THERAPEUTICS |
GB201801128D0 (en) | 2018-01-24 | 2018-03-07 | Univ Oxford Innovation Ltd | Compounds |
US11465975B2 (en) | 2018-02-08 | 2022-10-11 | Neupharma, Inc | Certain chemical entities, compositions, and methods |
WO2019175093A1 (en) | 2018-03-12 | 2019-09-19 | Astrazeneca Ab | Method for treating lung cancer |
PT3774817T (pt) | 2018-04-13 | 2023-03-09 | The Institute Of Cancer Res Royal Cancer Hospital | Inibidores de bcl6 |
FR3080620B1 (fr) * | 2018-04-27 | 2021-11-12 | Univ Paris Sud | Composes a activite inhibitrice de la polymerisation de la tubuline et aux proprietes immunomodulatrices |
GB201809102D0 (en) | 2018-06-04 | 2018-07-18 | Univ Oxford Innovation Ltd | Compounds |
EP3802519A1 (en) | 2018-06-04 | 2021-04-14 | Apros Therapeutics, Inc. | Pyrimidine compounds containing acidic groups useful to treat diseases connected to the modulation of tlr7 |
GB201810092D0 (en) | 2018-06-20 | 2018-08-08 | Ctxt Pty Ltd | Compounds |
GB201810581D0 (en) | 2018-06-28 | 2018-08-15 | Ctxt Pty Ltd | Compounds |
EP3852811A1 (en) | 2018-09-17 | 2021-07-28 | Sutro Biopharma, Inc. | Combination therapies with anti-folate receptor antibody conjugates |
WO2020057403A1 (zh) * | 2018-09-18 | 2020-03-26 | 北京越之康泰生物医药科技有限公司 | 吲哚衍生物及其在医药上的应用 |
MX2021003517A (es) | 2018-09-25 | 2021-08-16 | Black Diamond Therapeutics Inc | Composiciones de inhibidor de tirosina quinasa, metodos de fabricacion y metodos de uso. |
GB201819126D0 (en) | 2018-11-23 | 2019-01-09 | Cancer Research Tech Ltd | Inhibitor compounds |
CN111747950B (zh) | 2019-03-29 | 2024-01-23 | 深圳福沃药业有限公司 | 用于治疗癌症的嘧啶衍生物 |
JP2022528562A (ja) | 2019-04-05 | 2022-06-14 | ストーム・セラピューティクス・リミテッド | Mettl3阻害化合物 |
GB201905328D0 (en) | 2019-04-15 | 2019-05-29 | Azeria Therapeutics Ltd | Inhibitor compounds |
WO2020227105A1 (en) | 2019-05-03 | 2020-11-12 | Sutro Biopharma, Inc. | Anti-bcma antibody conjugates |
GB201908885D0 (en) | 2019-06-20 | 2019-08-07 | Storm Therapeutics Ltd | Therapeutic compounds |
JP2022545930A (ja) | 2019-08-31 | 2022-11-01 | 上海奕拓醫藥科技有限責任公司 | Fgfr阻害剤とするピラゾール類誘導体及びその調製方法 |
AU2020348489A1 (en) | 2019-09-20 | 2022-05-05 | Ideaya Biosciences, Inc. | 4-substituted indole and indazole sulfonamido derivatives as PARG inhibitors |
GB201913988D0 (en) | 2019-09-27 | 2019-11-13 | Celleron Therapeutics Ltd | Novel treatment |
GB201914860D0 (en) | 2019-10-14 | 2019-11-27 | Cancer Research Tech Ltd | Inhibitor compounds |
GB201915828D0 (en) | 2019-10-31 | 2019-12-18 | Cancer Research Tech Ltd | Compounds, compositions and therapeutic uses thereof |
GB201915829D0 (en) | 2019-10-31 | 2019-12-18 | Cancer Research Tech Ltd | Compounds, compositions and therapeutic uses thereof |
GB201915831D0 (en) | 2019-10-31 | 2019-12-18 | Cancer Research Tech Ltd | Compounds, compositions and therapeutic uses thereof |
AU2020394867A1 (en) | 2019-12-02 | 2022-05-26 | Storm Therapeutics Limited | Polyheterocyclic compounds as METTL3 inhibitors |
US20230095053A1 (en) | 2020-03-03 | 2023-03-30 | Sutro Biopharma, Inc. | Antibodies comprising site-specific glutamine tags, methods of their preparation and methods of their use |
GB202004960D0 (en) | 2020-04-03 | 2020-05-20 | Kinsenus Ltd | Inhibitor compounds |
GB202012969D0 (en) | 2020-08-19 | 2020-09-30 | Univ Of Oxford | Inhibitor compounds |
US20230391770A1 (en) | 2020-10-06 | 2023-12-07 | Storm Therapeutics Limited | Mettl3 inhibitory compounds |
US20240101589A1 (en) | 2020-10-08 | 2024-03-28 | Strom Therapeutics Limited | Inhibitors of mettl3 |
GB202102895D0 (en) | 2021-03-01 | 2021-04-14 | Cambridge Entpr Ltd | Novel compounds, compositions and therapeutic uses thereof |
KR20220156448A (ko) | 2021-05-17 | 2022-11-25 | 에이치케이이노엔 주식회사 | 벤즈아미드 유도체, 이의 제조방법 및 이를 유효성분으로 함유하는 암의 예방 또는 치료용 약학적 조성물 |
GB202107907D0 (en) | 2021-06-02 | 2021-07-14 | Storm Therapeutics Ltd | Combination therapies |
GB202108383D0 (en) | 2021-06-11 | 2021-07-28 | Argonaut Therapeutics Ltd | Compounds useful in the treatment or prevention of a prmt5-mediated disorder |
CA3225500A1 (en) | 2021-10-04 | 2023-04-13 | Ulrich Luecking | Parg inhibitory compounds |
WO2023057394A1 (en) | 2021-10-04 | 2023-04-13 | Forx Therapeutics Ag | N,n-dimethyl-4-(7-(n-(1-methylcyclopropyl)sulfamoyl)-imidazo[1,5-a]pyridin-5-yl)piperazine-1-carboxamide derivatives and the corresponding pyrazolo[1,5-a]pyridine derivatives as parg inhibitors for the treatment of cancer |
WO2023081923A1 (en) | 2021-11-08 | 2023-05-11 | Frequency Therapeutics, Inc. | Platelet-derived growth factor receptor (pdgfr) alpha inhibitors and uses thereof |
GB202202199D0 (en) | 2022-02-18 | 2022-04-06 | Cancer Research Tech Ltd | Compounds |
WO2023161881A1 (en) * | 2022-02-25 | 2023-08-31 | Glaxosmithkline Intellectual Property Development Limited | Cytotoxicity targeting chimeras for ccr2-expressing cells |
WO2023175185A1 (en) | 2022-03-17 | 2023-09-21 | Forx Therapeutics Ag | 2,4-dioxo-1,4-dihydroquinazoline derivatives as parg inhibitors for the treatment of cancer |
WO2023175184A1 (en) | 2022-03-17 | 2023-09-21 | Forx Therapeutics Ag | 2,4-dioxo-1,4-dihydroquinazoline derivatives as parg inhibitors for the treatment of cancer |
GB202204935D0 (en) | 2022-04-04 | 2022-05-18 | Cambridge Entpr Ltd | Nanoparticles |
GB202209404D0 (en) | 2022-06-27 | 2022-08-10 | Univ Of Sussex | Compounds |
WO2024006542A1 (en) | 2022-06-30 | 2024-01-04 | Sutro Biopharma, Inc. | Anti-ror1 antibodies and antibody conjugates, compositions comprising anti-ror1 antibodies or antibody conjugates, and methods of making and using anti-ror1 antibodies and antibody conjugates |
WO2024003241A1 (en) | 2022-06-30 | 2024-01-04 | Astrazeneca Ab | Treatment for immuno-oncology resistant subjects with an anti pd-l1 antibody an antisense targeted to stat3 and an inhibitor of ctla-4 |
WO2024030825A1 (en) | 2022-08-01 | 2024-02-08 | Neupharma, Inc | Crystalline salts of crystalline salts of (3s,5r,8r,9s,10s,13r,14s,17r)-14-hydroxy-10,13-dimethyl-17-(2- oxo-2h-pyran-5-yl)hexadecahydro-1h-cyclopenta[a]phenanthren-3-yl piperazine-1-carboxylate |
GB202213167D0 (en) | 2022-09-08 | 2022-10-26 | Cambridge Entpr Ltd | Novel compounds, compositions and therapeutic uses thereof |
GB202213164D0 (en) | 2022-09-08 | 2022-10-26 | Cambridge Entpr Ltd | Novel compounds, compositions and therapeutic uses thereof |
GB202213163D0 (en) | 2022-09-08 | 2022-10-26 | Cambridge Entpr Ltd | Novel compounds, compositions and therapeutic uses thereof |
GB202213166D0 (en) | 2022-09-08 | 2022-10-26 | Cambridge Entpr Ltd | Novel compounds, compositions and therapeutic uses thereof |
WO2024059169A1 (en) * | 2022-09-14 | 2024-03-21 | Blueprint Medicines Corporation | Egfr inhibitors |
WO2024074497A1 (en) | 2022-10-03 | 2024-04-11 | Forx Therapeutics Ag | Parg inhibitory compound |
WO2024094962A1 (en) | 2022-11-02 | 2024-05-10 | Cancer Research Technology Limited | Pyrido[2,3-d]pyrimidin-2-amine derivatives as egfr inhibitors for the treatment of cancer |
WO2024094963A1 (en) | 2022-11-02 | 2024-05-10 | Cancer Research Technology Limited | 2-amino-pyrido[2,3-d]pyrimidin-7(8h)-one and 7-amino-1-pyrimido[4,5-d]pyrimidin-2(1 h)-one derivatives as egfr inhibitors for the treatment of cancer |
Family Cites Families (61)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3557142A (en) * | 1968-02-20 | 1971-01-19 | Sterling Drug Inc | 4,5,6,7-tetrahydro-indole-lower-alkanoic acids and esters |
US4460584A (en) | 1981-03-13 | 1984-07-17 | Imperial Chemical Industries Plc | Nitrogen heterocycles |
IL81307A0 (en) | 1986-01-23 | 1987-08-31 | Union Carbide Agricult | Method for reducing moisture loss from plants and increasing crop yield utilizing nitrogen containing heterocyclic compounds and some novel polysubstituted pyridine derivatives |
IL89029A (en) | 1988-01-29 | 1993-01-31 | Lilly Co Eli | Fungicidal quinoline and cinnoline derivatives, compositions containing them, and fungicidal methods of using them |
US5411963A (en) | 1988-01-29 | 1995-05-02 | Dowelanco | Quinazoline derivatives |
GB8819307D0 (en) | 1988-08-13 | 1988-09-14 | Pfizer Ltd | Antiarrhythmic agents |
US5710158A (en) | 1991-05-10 | 1998-01-20 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
US6645969B1 (en) | 1991-05-10 | 2003-11-11 | Aventis Pharmaceuticals Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
US5480883A (en) | 1991-05-10 | 1996-01-02 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Bis mono- and bicyclic aryl and heteroaryl compounds which inhibit EGF and/or PDGF receptor tyrosine kinase |
US5714493A (en) | 1991-05-10 | 1998-02-03 | Rhone-Poulenc Rorer Pharmaceuticals, Inc. | Aryl and heteroaryl quinazoline compounds which inhibit CSF-1R receptor tyrosine kinase |
US5721237A (en) * | 1991-05-10 | 1998-02-24 | Rhone-Poulenc Rorer Pharmaceuticals Inc. | Protein tyrosine kinase aryl and heteroaryl quinazoline compounds having selective inhibition of HER-2 autophosphorylation properties |
ES2108120T3 (es) | 1991-05-10 | 1997-12-16 | Rhone Poulenc Rorer Int | Compuestos bis arilicos y heteroarilicos mono- y biciclicos que inhiben tirosina quinasa receptora de egf y/o pdgf. |
NZ243082A (en) | 1991-06-28 | 1995-02-24 | Ici Plc | 4-anilino-quinazoline derivatives; pharmaceutical compositions, preparatory processes, and use thereof |
AU661533B2 (en) | 1992-01-20 | 1995-07-27 | Astrazeneca Ab | Quinazoline derivatives |
GB9323290D0 (en) * | 1992-12-10 | 1994-01-05 | Zeneca Ltd | Quinazoline derivatives |
GB9314893D0 (en) | 1993-07-19 | 1993-09-01 | Zeneca Ltd | Quinazoline derivatives |
US5700823A (en) | 1994-01-07 | 1997-12-23 | Sugen, Inc. | Treatment of platelet derived growth factor related disorders such as cancers |
AU686843B2 (en) | 1994-02-23 | 1998-02-12 | Pfizer Inc. | 4-heterocyclyl-substituted quinazoline derivatives, processes for their preparation and their use as anti-cancer agents |
WO1995024190A2 (en) | 1994-03-07 | 1995-09-14 | Sugen, Inc. | Receptor tyrosine kinase inhibitors for inhibiting cell proliferative disorders and compositions thereof |
WO1996011187A1 (fr) | 1994-10-07 | 1996-04-18 | Zenyaku Kogyo Kabushiki Kaisha | Derive thioquinolone |
DE4436509A1 (de) * | 1994-10-13 | 1996-04-18 | Hoechst Schering Agrevo Gmbh | Substituierte Spiroalkylamino- und alkoxy-Heterocyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Schädlingsbekämpfungsmittel und Fungizide |
GB9505651D0 (en) | 1995-03-21 | 1995-05-10 | Agrevo Uk Ltd | AgrEvo UK Limited |
US6046206A (en) | 1995-06-07 | 2000-04-04 | Cell Pathways, Inc. | Method of treating a patient having a precancerous lesions with amide quinazoline derivatives |
GB9514265D0 (en) | 1995-07-13 | 1995-09-13 | Wellcome Found | Hetrocyclic compounds |
EP0860433B1 (en) | 1995-11-07 | 2002-07-03 | Kirin Beer Kabushiki Kaisha | Quinoline derivatives and quinazoline derivatives inhibiting autophosphorylation of growth factor receptor originating in platelet and pharmaceutical compositions containing the same |
GB9624482D0 (en) | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
GB9603095D0 (en) | 1996-02-14 | 1996-04-10 | Zeneca Ltd | Quinazoline derivatives |
DE19614718A1 (de) | 1996-04-15 | 1997-10-16 | Hoechst Schering Agrevo Gmbh | Substituierte Pyridine/Pyrimidine, Verfahren zu ihrer Herstellung, und ihre Verwendung als Schädlingsbekämpfungsmittel |
GB9707800D0 (en) | 1996-05-06 | 1997-06-04 | Zeneca Ltd | Chemical compounds |
GB9609641D0 (en) * | 1996-05-09 | 1996-07-10 | Pfizer Ltd | Compounds useful in therapy |
DK0912559T3 (da) | 1996-07-13 | 2003-03-10 | Glaxo Group Ltd | Kondenserede heterocykliske forbindelser som proteintyrosinkinaseinhibitorer |
US6809097B1 (en) * | 1996-09-25 | 2004-10-26 | Zeneca Limited | Quinoline derivatives inhibiting the effect of growth factors such as VEGF |
US6225318B1 (en) | 1996-10-17 | 2001-05-01 | Pfizer Inc | 4-aminoquinazolone derivatives |
EP0837063A1 (en) | 1996-10-17 | 1998-04-22 | Pfizer Inc. | 4-Aminoquinazoline derivatives |
EP0984692A4 (en) | 1997-05-30 | 2001-02-21 | Merck & Co Inc | ANGIOGENESIS INHIBITORS |
GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
ZA986729B (en) | 1997-07-29 | 1999-02-02 | Warner Lambert Co | Irreversible inhibitors of tyrosine kinases |
WO1999010349A1 (en) * | 1997-08-22 | 1999-03-04 | Zeneca Limited | Oxindolylquinazoline derivatives as angiogenesis inhibitors |
US6162804A (en) | 1997-09-26 | 2000-12-19 | Merck & Co., Inc. | Tyrosine kinase inhibitors |
GB9721437D0 (en) | 1997-10-10 | 1997-12-10 | Glaxo Group Ltd | Heteroaromatic compounds and their use in medicine |
WO1999028159A1 (de) | 1997-11-27 | 1999-06-10 | Continental Teves Ag & Co. Ohg | Verfahren und vorrichtung zum versorgen von kraftfahrzeugen mit daten oder zum datenaustausch |
GB9800569D0 (en) | 1998-01-12 | 1998-03-11 | Glaxo Group Ltd | Heterocyclic compounds |
GB9800575D0 (en) | 1998-01-12 | 1998-03-11 | Glaxo Group Ltd | Heterocyclic compounds |
US6172071B1 (en) | 1998-07-30 | 2001-01-09 | Hughes Institute | Lipid-lowering quinazoline derivative |
US6184226B1 (en) | 1998-08-28 | 2001-02-06 | Scios Inc. | Quinazoline derivatives as inhibitors of P-38 α |
GB2345486A (en) | 1999-01-11 | 2000-07-12 | Glaxo Group Ltd | Heteroaromatic protein tyrosine kinase inhibitors |
UA71945C2 (en) | 1999-01-27 | 2005-01-17 | Pfizer Prod Inc | Substituted bicyclic derivatives being used as anticancer agents |
JP3270834B2 (ja) | 1999-01-27 | 2002-04-02 | ファイザー・プロダクツ・インク | 抗がん剤として有用なヘテロ芳香族二環式誘導体 |
ATE482946T1 (de) * | 1999-02-10 | 2010-10-15 | Astrazeneca Ab | Chinazolinderivate als angiogenesehemmer und zwischenprodukte dafür |
DE19911509A1 (de) | 1999-03-15 | 2000-09-21 | Boehringer Ingelheim Pharma | Bicyclische Heterocyclen, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
TWI262914B (en) | 1999-07-02 | 2006-10-01 | Agouron Pharma | Compounds and pharmaceutical compositions for inhibiting protein kinases |
PE20010306A1 (es) | 1999-07-02 | 2001-03-29 | Agouron Pharma | Compuestos de indazol y composiciones farmaceuticas que los contienen utiles para la inhibicion de proteina kinasa |
CZ20021390A3 (cs) | 1999-10-19 | 2002-09-11 | Merck & Co., Inc. | Inhibitory tyrosinkinázy |
AU2001279938B2 (en) | 2000-08-09 | 2007-01-25 | Astrazeneca Ab | Indole, azaindole and indazole derivatives having VEGF inhibiting activity |
AU7653601A (en) | 2000-08-09 | 2002-02-18 | Astrazeneca Ab | Quinoline derivatives having vegf inhibiting activity |
CN1252065C (zh) | 2000-08-09 | 2006-04-19 | 阿斯特拉曾尼卡有限公司 | 噌啉化合物 |
PL371486A1 (en) * | 2002-02-01 | 2005-06-13 | Astrazeneca Ab | Quinazoline compounds |
GB0318422D0 (en) | 2003-08-06 | 2003-09-10 | Astrazeneca Ab | Chemical compounds |
GB0330002D0 (en) | 2003-12-24 | 2004-01-28 | Astrazeneca Ab | Quinazoline derivatives |
GB0523810D0 (en) * | 2005-11-23 | 2006-01-04 | Astrazeneca Ab | Pharmaceutical compositions |
US7851623B2 (en) | 2006-11-02 | 2010-12-14 | Astrazeneca Ab | Chemical process |
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2000
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