JPWO2020239952A5 - - Google Patents
Download PDFInfo
- Publication number
- JPWO2020239952A5 JPWO2020239952A5 JP2021570931A JP2021570931A JPWO2020239952A5 JP WO2020239952 A5 JPWO2020239952 A5 JP WO2020239952A5 JP 2021570931 A JP2021570931 A JP 2021570931A JP 2021570931 A JP2021570931 A JP 2021570931A JP WO2020239952 A5 JPWO2020239952 A5 JP WO2020239952A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- quinazolin
- amine
- methoxy
- ethyl
- 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
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 23
- 125000001072 heteroaryl group Chemical group 0.000 claims 23
- 125000005843 halogen group Chemical group 0.000 claims 17
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 17
- 125000003118 aryl group Chemical group 0.000 claims 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 14
- 125000002947 alkylene group Chemical group 0.000 claims 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 14
- 150000001412 amines Chemical class 0.000 claims 12
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 11
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 11
- 206010011224 Cough Diseases 0.000 claims 8
- -1 (R A R B )N- Chemical group 0.000 claims 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 6
- BPMVUJACSQFKAS-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NC(C)C=1SC(=NN=1)C)C=1SC(=CN=1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NC(C)C=1SC(=NN=1)C)C=1SC(=CN=1)C BPMVUJACSQFKAS-UHFFFAOYSA-N 0.000 claims 6
- RAFQASZWPFSIJL-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C1=CC=CC(N1)=O Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C1=CC=CC(N1)=O RAFQASZWPFSIJL-UHFFFAOYSA-N 0.000 claims 6
- BEAGZQGNOOVGIO-UHFFFAOYSA-N FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C1=NC(=NO1)C Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C1=NC(=NO1)C BEAGZQGNOOVGIO-UHFFFAOYSA-N 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000004043 oxo group Chemical group O=* 0.000 claims 5
- 125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims 4
- GTADTGLAOGYVSF-UHFFFAOYSA-N 6-(5-fluoropyridin-2-yl)-8-methoxy-N-[1-[6-(trifluoromethyl)pyridazin-3-yl]ethyl]quinazolin-4-amine Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1N=NC(=CC=1)C(F)(F)F GTADTGLAOGYVSF-UHFFFAOYSA-N 0.000 claims 4
- MOXNZYIXXWXDNF-UHFFFAOYSA-N 8-methoxy-6-(5-methylpyrimidin-2-yl)-N-[1-(5-methyl-1,3,4-thiadiazol-2-yl)ethyl]quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NC(C)C=1SC(=NN=1)C)C1=NC=C(C=N1)C MOXNZYIXXWXDNF-UHFFFAOYSA-N 0.000 claims 4
- ZXRFKVOCWKERRJ-UHFFFAOYSA-N 8-methoxy-6-(5-methylpyrimidin-2-yl)-N-[1-[6-(trifluoromethyl)pyridazin-3-yl]ethyl]quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NC(C)C=1N=NC(=CC=1)C(F)(F)F)C1=NC=C(C=N1)C ZXRFKVOCWKERRJ-UHFFFAOYSA-N 0.000 claims 4
- SFEXGNKDILHXSX-UHFFFAOYSA-N 8-methoxy-N-[1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]-6-(5-methylpyrimidin-2-yl)quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NC(C)C1=NC(=NO1)C)C1=NC=C(C=N1)C SFEXGNKDILHXSX-UHFFFAOYSA-N 0.000 claims 4
- CNOZNARJABWQET-UHFFFAOYSA-N CC1=CC=C(N=N1)C(C)NC1=NC=NC2=C(C=C(C=C12)C1=NC=C(C=N1)C)OC1CCOCC1 Chemical compound CC1=CC=C(N=N1)C(C)NC1=NC=NC2=C(C=C(C=C12)C1=NC=C(C=N1)C)OC1CCOCC1 CNOZNARJABWQET-UHFFFAOYSA-N 0.000 claims 4
- BFOFHOYBTLGLKZ-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NC(C)C1=NC(=NO1)C)C1=NC=C(C=C1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NC(C)C1=NC(=NO1)C)C1=NC=C(C=C1)C BFOFHOYBTLGLKZ-UHFFFAOYSA-N 0.000 claims 4
- KDGDLGFEPBRLIC-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NC(C)C=1SC(=NN=1)C)C1=NC=C(C=C1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NC(C)C=1SC(=NN=1)C)C1=NC=C(C=C1)C KDGDLGFEPBRLIC-UHFFFAOYSA-N 0.000 claims 4
- VREDKYBVIGZVPM-UHFFFAOYSA-N FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1SC(=NN=1)C Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1SC(=NN=1)C VREDKYBVIGZVPM-UHFFFAOYSA-N 0.000 claims 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 3
- BRNLTJHIGKXWIY-UHFFFAOYSA-N 6-(4-fluorophenyl)-N-[(6-methylpyridazin-3-yl)methyl]-8-(oxetan-3-yloxy)quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC1COC1)NCC=1N=NC(=CC=1)C BRNLTJHIGKXWIY-UHFFFAOYSA-N 0.000 claims 3
- RUIVBEVUNDSHKO-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NC(C)C1=NC(=NO1)C1=CC=NC=C1)C1=NC=C(C=N1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NC(C)C1=NC(=NO1)C1=CC=NC=C1)C1=NC=C(C=N1)C RUIVBEVUNDSHKO-UHFFFAOYSA-N 0.000 claims 3
- BMPWQDRELWVIJS-GFCCVEGCSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OCC(=O)O)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OCC(=O)O)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F BMPWQDRELWVIJS-GFCCVEGCSA-N 0.000 claims 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 3
- 208000013116 chronic cough Diseases 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000001301 oxygen Substances 0.000 claims 3
- UELDKBXAUWNGDS-UHFFFAOYSA-N 2-[4-[(6-methylpyridazin-3-yl)methylamino]-6-(5-methylpyrimidin-2-yl)quinazolin-8-yl]oxyacetic acid dihydrochloride Chemical compound Cl.Cl.CC1=CC=C(N=N1)CNC1=NC=NC2=C(C=C(C=C12)C1=NC=C(C=N1)C)OCC(=O)O UELDKBXAUWNGDS-UHFFFAOYSA-N 0.000 claims 2
- DPASNAOQCAPJJT-UHFFFAOYSA-N 4-[[[6-(5-fluoropyridin-2-yl)-8-methoxyquinazolin-4-yl]amino]methyl]-1H-pyridin-2-one Chemical compound COC(C=C(C=C12)C(C=C3)=NC=C3F)=C1N=CN=C2NCC(C=CN1)=CC1=O DPASNAOQCAPJJT-UHFFFAOYSA-N 0.000 claims 2
- SUQZVIXPCVZNLS-UHFFFAOYSA-N 4-[[[8-methoxy-6-(5-methyl-1,3-thiazol-2-yl)quinazolin-4-yl]amino]methyl]-1-methylpyridin-2-one Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC1=CC(N(C=C1)C)=O)C=1SC(=CN=1)C SUQZVIXPCVZNLS-UHFFFAOYSA-N 0.000 claims 2
- CSFOVBHMLMYNPT-UHFFFAOYSA-N 6-(3-chloropyrazol-1-yl)-8-methoxy-N-[1-(6-methylpyridazin-3-yl)ethyl]quinazolin-4-amine Chemical compound ClC1=NN(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1N=NC(=CC=1)C CSFOVBHMLMYNPT-UHFFFAOYSA-N 0.000 claims 2
- IVTJNEUOTNRNAM-SNVBAGLBSA-N 6-(4-chloropyrazol-1-yl)-8-methoxy-N-[(1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]quinazolin-4-amine Chemical compound ClC=1C=NN(C=1)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F IVTJNEUOTNRNAM-SNVBAGLBSA-N 0.000 claims 2
- BQFNJNBPNARBNE-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-[(3-methyloxetan-3-yl)methoxy]-N-[(6-methylpyridazin-3-yl)methyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OCC1(COC1)C)NCC=1N=NC(=CC=1)C BQFNJNBPNARBNE-UHFFFAOYSA-N 0.000 claims 2
- PFQHDBNHULBMGF-GFCCVEGCSA-N 6-(4-fluoropyrazol-1-yl)-8-methoxy-N-[(1R)-1-(6-methylpyridazin-3-yl)ethyl]quinazolin-4-amine Chemical compound FC=1C=NN(C=1)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@H](C)C=1N=NC(=CC=1)C PFQHDBNHULBMGF-GFCCVEGCSA-N 0.000 claims 2
- VDFYWJLTHTYFGN-SNVBAGLBSA-N 6-(4-fluoropyrazol-1-yl)-8-methoxy-N-[(1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]quinazolin-4-amine Chemical compound FC=1C=NN(C=1)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F VDFYWJLTHTYFGN-SNVBAGLBSA-N 0.000 claims 2
- NGSLBCPVAVJNFF-UHFFFAOYSA-N 6-(5-fluoropyridin-2-yl)-8-methoxy-N-[(5-methyl-1,2-oxazol-3-yl)methyl]quinazolin-4-amine Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=NOC(=C1)C NGSLBCPVAVJNFF-UHFFFAOYSA-N 0.000 claims 2
- WEQRGBLNZUKKPY-UHFFFAOYSA-N 6-(5-fluoropyridin-2-yl)-8-methoxy-N-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]quinazolin-4-amine Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC=1OC(=NN=1)C WEQRGBLNZUKKPY-UHFFFAOYSA-N 0.000 claims 2
- YWCYJKQUNMLEOR-CYBMUJFWSA-N 6-(5-fluoropyridin-2-yl)-N-[(1R)-1-(5-methyl-1,2,4-oxadiazol-3-yl)ethyl]-8-(oxan-4-yloxy)quinazolin-4-amine Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC1CCOCC1)N[C@H](C)C1=NOC(=N1)C YWCYJKQUNMLEOR-CYBMUJFWSA-N 0.000 claims 2
- CNWURNWCUQERPZ-UHFFFAOYSA-N 6-(5-fluoropyridin-2-yl)-N-[(6-methylpyridazin-3-yl)methyl]-8-(oxan-4-yloxy)quinazolin-4-amine Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC1CCOCC1)NCC=1N=NC(=CC=1)C CNWURNWCUQERPZ-UHFFFAOYSA-N 0.000 claims 2
- MPSFCYFXWFAIIZ-GFCCVEGCSA-N 6-(5-fluoropyrimidin-2-yl)-8-methoxy-N-[(1R)-1-(6-methylpyridazin-3-yl)ethyl]quinazolin-4-amine Chemical compound FC=1C=NC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@H](C)C=1N=NC(=CC=1)C MPSFCYFXWFAIIZ-GFCCVEGCSA-N 0.000 claims 2
- ASTMHSCHESBZOQ-UHFFFAOYSA-N 6-(5-fluoropyrimidin-2-yl)-8-methoxy-N-[1-(3-methyl-1,2,4-oxadiazol-5-yl)ethyl]quinazolin-4-amine Chemical compound FC=1C=NC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C1=NC(=NO1)C ASTMHSCHESBZOQ-UHFFFAOYSA-N 0.000 claims 2
- RDRJHYZLFBGPEZ-UHFFFAOYSA-N 6-(5-fluoropyrimidin-2-yl)-8-methoxy-N-[1-(5-methyl-1,2,4-oxadiazol-3-yl)ethyl]quinazolin-4-amine Chemical compound FC=1C=NC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C1=NOC(=N1)C RDRJHYZLFBGPEZ-UHFFFAOYSA-N 0.000 claims 2
- RZGOPJNPFUCYGK-UHFFFAOYSA-N 6-(5-fluoropyrimidin-2-yl)-8-methoxy-N-[1-(5-methyl-1,3,4-thiadiazol-2-yl)ethyl]quinazolin-4-amine Chemical compound FC=1C=NC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1SC(=NN=1)C RZGOPJNPFUCYGK-UHFFFAOYSA-N 0.000 claims 2
- GFGPECISMQULKS-OAHLLOKOSA-N 6-(5-methyl-1,3-thiazol-2-yl)-8-(oxan-4-yloxy)-N-[(1R)-1-pyridazin-3-ylethyl]quinazolin-4-amine Chemical compound CC1=CN=C(S1)C=1C=C2C(=NC=NC2=C(C=1)OC1CCOCC1)N[C@H](C)C=1N=NC=CC=1 GFGPECISMQULKS-OAHLLOKOSA-N 0.000 claims 2
- GGYNPZNUGUJLHG-LLVKDONJSA-N 8-methoxy-N-[(1R)-1-(5-methyl-1,2,4-oxadiazol-3-yl)ethyl]-6-(5-methylpyrimidin-2-yl)quinazolin-4-amine Chemical class COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C1=NOC(=N1)C)C1=NC=C(C=N1)C GGYNPZNUGUJLHG-LLVKDONJSA-N 0.000 claims 2
- VCDNIFWIDVGQLK-UHFFFAOYSA-N 8-methoxy-N-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-(5-methyl-1,3-thiazol-2-yl)quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC1=NC(=NO1)C)C=1SC(=CN=1)C VCDNIFWIDVGQLK-UHFFFAOYSA-N 0.000 claims 2
- NZLGKTRCRRRGBN-UHFFFAOYSA-N 8-methoxy-N-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-(5-methylpyridin-2-yl)quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC1=NC(=NO1)C)C1=NC=C(C=C1)C NZLGKTRCRRRGBN-UHFFFAOYSA-N 0.000 claims 2
- BVQVQNDRCJENQL-UHFFFAOYSA-N 8-methoxy-N-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]-6-(5-methylpyrimidin-2-yl)quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC1=NC(=NO1)C)C1=NC=C(C=N1)C BVQVQNDRCJENQL-UHFFFAOYSA-N 0.000 claims 2
- PLLKZWXYZJVDEU-UHFFFAOYSA-N 8-methoxy-N-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]-6-(5-methylpyridin-2-yl)quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC1=NOC(=N1)C)C1=NC=C(C=C1)C PLLKZWXYZJVDEU-UHFFFAOYSA-N 0.000 claims 2
- FHOKWFLBJSTPTQ-UHFFFAOYSA-N 8-methoxy-N-[(5-methyl-1,2-oxazol-3-yl)methyl]-6-(5-methylpyridin-2-yl)quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC1=NOC(=C1)C)C1=NC=C(C=C1)C FHOKWFLBJSTPTQ-UHFFFAOYSA-N 0.000 claims 2
- SQLWDDGMNVWEPG-UHFFFAOYSA-N 8-methoxy-N-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]-6-(5-methylpyridin-2-yl)quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC=1OC(=NN=1)C)C1=NC=C(C=C1)C SQLWDDGMNVWEPG-UHFFFAOYSA-N 0.000 claims 2
- CWPOPFWWEUKGEJ-UHFFFAOYSA-N 8-methoxy-N-[1-(5-methyl-1,2,4-oxadiazol-3-yl)ethyl]-6-(5-methyl-1,3-thiazol-2-yl)quinazolin-4-amine Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NC(C)C1=NOC(=N1)C)C=1SC(=CN=1)C CWPOPFWWEUKGEJ-UHFFFAOYSA-N 0.000 claims 2
- JVKXWTBEXNKBSJ-YDALLXLXSA-N C(=O)O.FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C1)OC)N[C@@H](C)C=1C=NC(=NC1)C(F)(F)F Chemical compound C(=O)O.FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C1)OC)N[C@@H](C)C=1C=NC(=NC1)C(F)(F)F JVKXWTBEXNKBSJ-YDALLXLXSA-N 0.000 claims 2
- HQQWJYNUXGHZFT-UHFFFAOYSA-N CC1=CC=C(N=N1)CNC1=NC=NC2=C(C=C(C=C12)C=1SC(=CN=1)C)OCCO Chemical compound CC1=CC=C(N=N1)CNC1=NC=NC2=C(C=C(C=C12)C=1SC(=CN=1)C)OCCO HQQWJYNUXGHZFT-UHFFFAOYSA-N 0.000 claims 2
- ZIYZXCRGFFDVDH-UHFFFAOYSA-N CC1=NN=C(S1)C(C)NC1=NC=NC2=C(C=C(C=C12)C=1SC(=CN=1)C)OC1CCOCC1 Chemical class CC1=NN=C(S1)C(C)NC1=NC=NC2=C(C=C(C=C12)C=1SC(=CN=1)C)OC1CCOCC1 ZIYZXCRGFFDVDH-UHFFFAOYSA-N 0.000 claims 2
- LHKJFGJVUKPWCW-MRXNPFEDSA-N CN1N=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC1CCOCC1)N[C@H](C)C=1N=NC(=CC=1)C Chemical compound CN1N=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC1CCOCC1)N[C@H](C)C=1N=NC(=CC=1)C LHKJFGJVUKPWCW-MRXNPFEDSA-N 0.000 claims 2
- KVRQGPRQLJIELD-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NC(C)C=1OC(=NN=1)C)C1=NN(C=C1)C Chemical class COC=1C=C(C=C2C(=NC=NC=12)NC(C)C=1OC(=NN=1)C)C1=NN(C=C1)C KVRQGPRQLJIELD-UHFFFAOYSA-N 0.000 claims 2
- QEZJNBZIWMMJJA-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NCC1=CC(=NO1)C)C1=NC=C(C=C1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC1=CC(=NO1)C)C1=NC=C(C=C1)C QEZJNBZIWMMJJA-UHFFFAOYSA-N 0.000 claims 2
- AYUXDBZSKSNYOR-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NCC1=CC(=NO1)C)C=1SC(=CN=1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC1=CC(=NO1)C)C=1SC(=CN=1)C AYUXDBZSKSNYOR-UHFFFAOYSA-N 0.000 claims 2
- NKOPUBTYJXAHKN-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NCC1=CC(N(C=C1)C)=O)C1=NC=C(C=N1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC1=CC(N(C=C1)C)=O)C1=NC=C(C=N1)C NKOPUBTYJXAHKN-UHFFFAOYSA-N 0.000 claims 2
- ZWVSXQNDFLLREJ-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NCC1=CC=CC(N1)=O)C1=NC=C(C=N1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC1=CC=CC(N1)=O)C1=NC=C(C=N1)C ZWVSXQNDFLLREJ-UHFFFAOYSA-N 0.000 claims 2
- FNDSNDYMLLXPLM-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NCC1=NC(=NO1)C(F)(F)F)C1=NC=C(C=N1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC1=NC(=NO1)C(F)(F)F)C1=NC=C(C=N1)C FNDSNDYMLLXPLM-UHFFFAOYSA-N 0.000 claims 2
- KJIYFKXQJXUFNK-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NCC1=NC(=NO1)C(F)(F)F)C=1SC(=CN=1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC1=NC(=NO1)C(F)(F)F)C=1SC(=CN=1)C KJIYFKXQJXUFNK-UHFFFAOYSA-N 0.000 claims 2
- XCZYMTBITXCELU-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NCC1=NC=C(C=C1)C(F)(F)F)C=1SC(=CN=1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC1=NC=C(C=C1)C(F)(F)F)C=1SC(=CN=1)C XCZYMTBITXCELU-UHFFFAOYSA-N 0.000 claims 2
- ODAQTFBUQZYFCV-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NCC1=NN(C=C1)C)C1=NC=C(C=C1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC1=NN(C=C1)C)C1=NC=C(C=C1)C ODAQTFBUQZYFCV-UHFFFAOYSA-N 0.000 claims 2
- WQUNPXBURLTFTJ-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NCC=1C=NC(=CC=1)C)C1=NC=C(C=N1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC=1C=NC(=CC=1)C)C1=NC=C(C=N1)C WQUNPXBURLTFTJ-UHFFFAOYSA-N 0.000 claims 2
- RZVUSUAJSFZNOQ-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NCC=1C=NC(=NC=1)C(F)(F)F)C1=NC=C(C=N1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC=1C=NC(=NC=1)C(F)(F)F)C1=NC=C(C=N1)C RZVUSUAJSFZNOQ-UHFFFAOYSA-N 0.000 claims 2
- ZGTXMMZHFWSCOG-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NCC=1SC(=NN=1)C)C1=NC=C(C=N1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC=1SC(=NN=1)C)C1=NC=C(C=N1)C ZGTXMMZHFWSCOG-UHFFFAOYSA-N 0.000 claims 2
- WTZXSDFDWAIENB-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NCC=1SC(=NN=1)C)C=1SC(=CN=1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC=1SC(=NN=1)C)C=1SC(=CN=1)C WTZXSDFDWAIENB-UHFFFAOYSA-N 0.000 claims 2
- UYOLUDJCIFTICT-CQSZACIVSA-N COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C1=NN(C=C1)C)C1=NC=C(C=C1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C1=NN(C=C1)C)C1=NC=C(C=C1)C UYOLUDJCIFTICT-CQSZACIVSA-N 0.000 claims 2
- SDMPQQSNFXWVNX-CYBMUJFWSA-N COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C=1N=NC(=CC=1)C)C=1SC(=CN=1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C=1N=NC(=CC=1)C)C=1SC(=CN=1)C SDMPQQSNFXWVNX-CYBMUJFWSA-N 0.000 claims 2
- OMFAQEYFGKWKQG-CQSZACIVSA-N COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C=1N=NC(=CC=1)C)N1N=C(C=C1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C=1N=NC(=CC=1)C)N1N=C(C=C1)C OMFAQEYFGKWKQG-CQSZACIVSA-N 0.000 claims 2
- JXDZWSNRBJKJHW-CQSZACIVSA-N COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C=1N=NC(=CC=1)C)N1N=CC(=C1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C=1N=NC(=CC=1)C)N1N=CC(=C1)C JXDZWSNRBJKJHW-CQSZACIVSA-N 0.000 claims 2
- KCKRXCWUJZMJLB-CQSZACIVSA-N COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C=1N=NC(=CC=1)C)N1N=CC=C1C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C=1N=NC(=CC=1)C)N1N=CC=C1C KCKRXCWUJZMJLB-CQSZACIVSA-N 0.000 claims 2
- GDHYTEXJAJFPAA-UHFFFAOYSA-N COCCOC=1C=C(C=C2C(=NC=NC=12)NCC=1N=NC(=CC=1)C)C=1SC(=CN=1)C Chemical compound COCCOC=1C=C(C=C2C(=NC=NC=12)NCC=1N=NC(=CC=1)C)C=1SC(=CN=1)C GDHYTEXJAJFPAA-UHFFFAOYSA-N 0.000 claims 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- MQNXAQDBJOACTL-UHFFFAOYSA-N Cl.FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OCC(=O)O)NCC1CCN(CC1)C Chemical compound Cl.FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OCC(=O)O)NCC1CCN(CC1)C MQNXAQDBJOACTL-UHFFFAOYSA-N 0.000 claims 2
- CGKXPDZOXZNVSZ-UHFFFAOYSA-N ClC1=NN(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1C=NC(=NC=1)C(F)(F)F Chemical compound ClC1=NN(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1C=NC(=NC=1)C(F)(F)F CGKXPDZOXZNVSZ-UHFFFAOYSA-N 0.000 claims 2
- GMVDIMXWRPGXDJ-GFCCVEGCSA-N ClC=1C=NN(C=1)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@H](C)C=1N=NC(=CC=1)C Chemical compound ClC=1C=NN(C=1)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@H](C)C=1N=NC(=CC=1)C GMVDIMXWRPGXDJ-GFCCVEGCSA-N 0.000 claims 2
- SSEAIMDZIFDWQP-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=NC=C(C=C1)F Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=NC=C(C=C1)F SSEAIMDZIFDWQP-UHFFFAOYSA-N 0.000 claims 2
- OKQMVSSPAKWHIH-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC1C(N(CC1)C)=O)NCC=1N=NC(=CC=1)C Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC1C(N(CC1)C)=O)NCC=1N=NC(=CC=1)C OKQMVSSPAKWHIH-UHFFFAOYSA-N 0.000 claims 2
- GZEDHHMQRGUYEK-GFCCVEGCSA-N FC1=NN(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@H](C)C=1N=NC(=CC=1)C Chemical compound FC1=NN(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@H](C)C=1N=NC(=CC=1)C GZEDHHMQRGUYEK-GFCCVEGCSA-N 0.000 claims 2
- LPKPCBSDZFYFFX-LLVKDONJSA-N FC=1C(=NC=C(C=1)C)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@H](C)C1=NOC(=N1)C Chemical compound FC=1C(=NC=C(C=1)C)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@H](C)C1=NOC(=N1)C LPKPCBSDZFYFFX-LLVKDONJSA-N 0.000 claims 2
- OBUNHRBGHKPZGK-UHFFFAOYSA-N FC=1C(=NC=C(C=1)F)CNC1=NC=NC2=C(C=C(C=C12)C=1SC(=CN=1)C)OC Chemical compound FC=1C(=NC=C(C=1)F)CNC1=NC=NC2=C(C=C(C=C12)C=1SC(=CN=1)C)OC OBUNHRBGHKPZGK-UHFFFAOYSA-N 0.000 claims 2
- KQOMUQWSRHRBCJ-UHFFFAOYSA-N FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=CC(=NO1)C Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=CC(=NO1)C KQOMUQWSRHRBCJ-UHFFFAOYSA-N 0.000 claims 2
- AKIJZXNIXJXYMI-UHFFFAOYSA-N FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=CC(N(C=C1)C)=O Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=CC(N(C=C1)C)=O AKIJZXNIXJXYMI-UHFFFAOYSA-N 0.000 claims 2
- YKJRZBWOQWXSCX-UHFFFAOYSA-N FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=NC(=NO1)C Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=NC(=NO1)C YKJRZBWOQWXSCX-UHFFFAOYSA-N 0.000 claims 2
- CEAZICSUCBTFRA-UHFFFAOYSA-N FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=NN(C=C1)C Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=NN(C=C1)C CEAZICSUCBTFRA-UHFFFAOYSA-N 0.000 claims 2
- DCIDIPCGFCGRKZ-UHFFFAOYSA-N FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=NOC(=N1)C Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC1=NOC(=N1)C DCIDIPCGFCGRKZ-UHFFFAOYSA-N 0.000 claims 2
- KRKKIRQNZIQXQV-UHFFFAOYSA-N FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC=1C=NC(=CC=1)C Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC=1C=NC(=CC=1)C KRKKIRQNZIQXQV-UHFFFAOYSA-N 0.000 claims 2
- POSFKSCFQRBHJP-UHFFFAOYSA-N FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC=1C=NC(=NC=1)C(F)(F)F Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC=1C=NC(=NC=1)C(F)(F)F POSFKSCFQRBHJP-UHFFFAOYSA-N 0.000 claims 2
- NUNAAXJPALZEQG-GFCCVEGCSA-N FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@H](C)C1=NN(C=C1)C Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)N[C@H](C)C1=NN(C=C1)C NUNAAXJPALZEQG-GFCCVEGCSA-N 0.000 claims 2
- XUUASSDYSNTOBL-UHFFFAOYSA-N FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC1CCOCC1)NC(C)C1=NC(=NO1)C Chemical compound FC=1C=CC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC1CCOCC1)NC(C)C1=NC(=NO1)C XUUASSDYSNTOBL-UHFFFAOYSA-N 0.000 claims 2
- VNMZIVPIMAOVIV-UHFFFAOYSA-N FC=1C=CC(=NC=1)CNC1=NC=NC2=C(C=C(C=C12)C=1SC(=CN=1)C)OC Chemical compound FC=1C=CC(=NC=1)CNC1=NC=NC2=C(C=C(C=C12)C=1SC(=CN=1)C)OC VNMZIVPIMAOVIV-UHFFFAOYSA-N 0.000 claims 2
- HYSRVHRIJWYEDR-UHFFFAOYSA-N FC=1C=NC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1OC(=NN=1)C Chemical compound FC=1C=NC(=NC=1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C=1OC(=NN=1)C HYSRVHRIJWYEDR-UHFFFAOYSA-N 0.000 claims 2
- 201000009794 Idiopathic Pulmonary Fibrosis Diseases 0.000 claims 2
- CHMVMBBUNZZTKA-UHFFFAOYSA-N N-[(5-chloropyridin-2-yl)methyl]-8-methoxy-6-(5-methyl-1,3-thiazol-2-yl)quinazolin-4-amine Chemical compound ClC=1C=CC(=NC=1)CNC1=NC=NC2=C(C=C(C=C12)C=1SC(=CN=1)C)OC CHMVMBBUNZZTKA-UHFFFAOYSA-N 0.000 claims 2
- MWNPQWWFKMWSKH-UHFFFAOYSA-N N-[(6-methylpyridazin-3-yl)methyl]-6-(5-methyl-1,3-thiazol-2-yl)-8-(oxan-4-yloxy)quinazolin-4-amine Chemical compound CC1=CC=C(N=N1)CNC1=NC=NC2=C(C=C(C=C12)C=1SC(=CN=1)C)OC1CCOCC1 MWNPQWWFKMWSKH-UHFFFAOYSA-N 0.000 claims 2
- NIVXWPHLERREPM-UHFFFAOYSA-N N-[(6-methylpyridazin-3-yl)methyl]-6-(5-methyl-1,3-thiazol-2-yl)-8-(oxetan-3-ylmethoxy)quinazolin-4-amine Chemical compound CC1=CC=C(N=N1)CNC1=NC=NC2=C(C=C(C=C12)C=1SC(=CN=1)C)OCC1COC1 NIVXWPHLERREPM-UHFFFAOYSA-N 0.000 claims 2
- NIMNDWXFYMWTKZ-UHFFFAOYSA-N N-[(6-methylpyridazin-3-yl)methyl]-6-(5-methylpyrimidin-2-yl)-8-(oxan-4-yloxy)quinazolin-4-amine Chemical compound CC1=CC=C(N=N1)CNC1=NC=NC2=C(C=C(C=C12)C1=NC=C(C=N1)C)OC1CCOCC1 NIMNDWXFYMWTKZ-UHFFFAOYSA-N 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 208000036971 interstitial lung disease 2 Diseases 0.000 claims 2
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims 2
- 208000023504 respiratory system disease Diseases 0.000 claims 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims 1
- IOCBPZQFQNHJMR-UHFFFAOYSA-N 2-[6-(4-fluorophenyl)-4-[(6-methylpyridazin-3-yl)methylamino]quinazolin-8-yl]oxy-N-(2,2,2-trifluoroethyl)acetamide Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OCC(=O)NCC(F)(F)F)NCC=1N=NC(=CC=1)C IOCBPZQFQNHJMR-UHFFFAOYSA-N 0.000 claims 1
- JKSMYOCCGRGEOV-UHFFFAOYSA-N 6-(3,6-dihydro-2H-pyran-4-yl)-8-methoxy-N-[(6-methylpyridazin-3-yl)methyl]quinazolin-4-amine Chemical compound O1CCC(=CC1)C=1C=C2C(=NC=NC2=C(C=1)OC)NCC=1N=NC(=CC=1)C JKSMYOCCGRGEOV-UHFFFAOYSA-N 0.000 claims 1
- QPCPUHGENQLVKS-OAHLLOKOSA-N 6-(4-fluorophenyl)-8-(1,2,3,6-tetrahydropyridin-4-yl)-N-[(1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)C=1CCNCC=1)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F QPCPUHGENQLVKS-OAHLLOKOSA-N 0.000 claims 1
- RASCKORQFCAIRQ-UHFFFAOYSA-N 6-(4-fluorophenyl)-8-methoxy-N-[1-(3-pyridin-4-yl-1,2,4-oxadiazol-5-yl)ethyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)OC)NC(C)C1=NC(=NO1)C1=CC=NC=C1 RASCKORQFCAIRQ-UHFFFAOYSA-N 0.000 claims 1
- OITDELSYLCLRLI-OAHLLOKOSA-N 6-(4-fluorophenyl)-8-morpholin-4-ylsulfonyl-N-[(1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]quinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)S(=O)(=O)N1CCOCC1)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F OITDELSYLCLRLI-OAHLLOKOSA-N 0.000 claims 1
- YWWYRHQDMDMIRC-OAHLLOKOSA-N 6-(4-fluorophenyl)-N,N-dimethyl-4-[[(1R)-1-(6-methylpyridazin-3-yl)ethyl]amino]quinazoline-8-sulfonamide Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)S(=O)(=O)N(C)C)N[C@H](C)C=1N=NC(=CC=1)C YWWYRHQDMDMIRC-OAHLLOKOSA-N 0.000 claims 1
- CVXGFTCNUQQCKY-QGZVFWFLSA-N 6-(4-fluorophenyl)-N-[(1R)-1-(6-methylpyridazin-3-yl)ethyl]-8-morpholin-4-ylsulfonylquinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)S(=O)(=O)N1CCOCC1)N[C@H](C)C=1N=NC(=CC=1)C CVXGFTCNUQQCKY-QGZVFWFLSA-N 0.000 claims 1
- MZLKYBKWPSGBOI-QGZVFWFLSA-N 6-(4-fluorophenyl)-N-[(1R)-1-(6-methylpyridazin-3-yl)ethyl]-8-piperazin-1-ylsulfonylquinazolin-4-amine Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)S(=O)(=O)N1CCNCC1)N[C@H](C)C=1N=NC(=CC=1)C MZLKYBKWPSGBOI-QGZVFWFLSA-N 0.000 claims 1
- LCHXKQARHDPLKJ-LLVKDONJSA-N 6-(4-fluorophenyl)-N-methyl-4-[[(1R)-1-(5-methyl-1,2,4-oxadiazol-3-yl)ethyl]amino]quinazoline-8-sulfonamide Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)S(=O)(=O)NC)N[C@H](C)C1=NOC(=N1)C LCHXKQARHDPLKJ-LLVKDONJSA-N 0.000 claims 1
- KOCBLWNEAICRDA-PLEWWHCXSA-N 8-(5-azaspiro[3.5]nonan-8-yloxy)-6-(4-fluorophenyl)-N-[(1R)-1-[2-(trifluoromethyl)pyrimidin-5-yl]ethyl]quinazolin-4-amine Chemical compound C1CCC11NCCC(C1)OC=1C=C(C=C2C(=NC=NC=12)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F)C1=CC=C(C=C1)F KOCBLWNEAICRDA-PLEWWHCXSA-N 0.000 claims 1
- 208000009079 Bronchial Spasm Diseases 0.000 claims 1
- 208000014181 Bronchial disease Diseases 0.000 claims 1
- 206010006482 Bronchospasm Diseases 0.000 claims 1
- VKOHZTBRPBMRMO-AOECRULISA-N C12NCC(C(C1)OC=1C=C(C=C3C(=NC=NC=13)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F)C1=CC=C(C=C1)F)C2 Chemical compound C12NCC(C(C1)OC=1C=C(C=C3C(=NC=NC=13)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F)C1=CC=C(C=C1)F)C2 VKOHZTBRPBMRMO-AOECRULISA-N 0.000 claims 1
- XWIYMLBMMHDGOC-UHFFFAOYSA-N CC1=CC=C(N=N1)C(C)NC1=NC=NC2=C(C=C(C=C12)C1=NC=C(C=N1)C)OCC1(CCOCC1)O Chemical compound CC1=CC=C(N=N1)C(C)NC1=NC=NC2=C(C=C(C=C12)C1=NC=C(C=N1)C)OCC1(CCOCC1)O XWIYMLBMMHDGOC-UHFFFAOYSA-N 0.000 claims 1
- NRFMMOOQSJSLTF-UHFFFAOYSA-N COC=1C=C(C=C2C(=NC=NC=12)NCC(=O)N1CCOCC1)C1=NC=C(C=N1)C Chemical compound COC=1C=C(C=C2C(=NC=NC=12)NCC(=O)N1CCOCC1)C1=NC=C(C=N1)C NRFMMOOQSJSLTF-UHFFFAOYSA-N 0.000 claims 1
- AYHNTWQQXVEDBW-CQSZACIVSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)C1=CN=NC=C1)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)C1=CN=NC=C1)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F AYHNTWQQXVEDBW-CQSZACIVSA-N 0.000 claims 1
- BNFJLUBUGNRBBP-OAHLLOKOSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)C1CCOCC1)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)C1CCOCC1)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F BNFJLUBUGNRBBP-OAHLLOKOSA-N 0.000 claims 1
- YKECREMBHVBRAD-CQSZACIVSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)C=1C=NC=NC=1)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)C=1C=NC=NC=1)N[C@H](C)C=1C=NC(=NC=1)C(F)(F)F YKECREMBHVBRAD-CQSZACIVSA-N 0.000 claims 1
- NUBQTJPUZUJFOM-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)C=1N(N=CC=1)C)NCC=1N=NC(=CC=1)C Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)C=1N(N=CC=1)C)NCC=1N=NC(=CC=1)C NUBQTJPUZUJFOM-UHFFFAOYSA-N 0.000 claims 1
- POLCBUQGOULOBW-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)S(=O)(=O)N(C)C)NC(C)C1=NOC(=N1)C Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)S(=O)(=O)N(C)C)NC(C)C1=NOC(=N1)C POLCBUQGOULOBW-UHFFFAOYSA-N 0.000 claims 1
- DFKSXZQDJJWAFA-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)S(=O)(=O)N(C)C)NC(C)C=1SC(=NN=1)C Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)S(=O)(=O)N(C)C)NC(C)C=1SC(=NN=1)C DFKSXZQDJJWAFA-UHFFFAOYSA-N 0.000 claims 1
- RBUARGSIXDJRJS-CQSZACIVSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)S(=O)(=O)N1CCNCC1)N[C@H](C)C1=NOC(=N1)C Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)S(=O)(=O)N1CCNCC1)N[C@H](C)C1=NOC(=N1)C RBUARGSIXDJRJS-CQSZACIVSA-N 0.000 claims 1
- ULWNZWILUFFRPZ-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)S(=O)(=O)N1CCOCC1)NC(C)C=1SC(=NN=1)C Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)S(=O)(=O)N1CCOCC1)NC(C)C=1SC(=NN=1)C ULWNZWILUFFRPZ-UHFFFAOYSA-N 0.000 claims 1
- CCQIRXVUWKBRFZ-UHFFFAOYSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)S(=O)(=O)NC)NC(C)C=1SC(=NN=1)C Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)S(=O)(=O)NC)NC(C)C=1SC(=NN=1)C CCQIRXVUWKBRFZ-UHFFFAOYSA-N 0.000 claims 1
- DVVMOBIWFGFUBN-CQSZACIVSA-N FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)S(=O)(=O)NC)N[C@H](C)C=1N=NC(=CC=1)C Chemical compound FC1=CC=C(C=C1)C=1C=C2C(=NC=NC2=C(C=1)S(=O)(=O)NC)N[C@H](C)C=1N=NC(=CC=1)C DVVMOBIWFGFUBN-CQSZACIVSA-N 0.000 claims 1
- 102100040460 P2X purinoceptor 3 Human genes 0.000 claims 1
- 101710189970 P2X purinoceptor 3 Proteins 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 1
- 230000000642 iatrogenic effect Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP19177604 | 2019-05-31 | ||
| EP19177604.6 | 2019-05-31 | ||
| EP19201168 | 2019-10-02 | ||
| EP19201168.2 | 2019-10-02 | ||
| PCT/EP2020/064914 WO2020239952A1 (en) | 2019-05-31 | 2020-05-28 | Amino quinazoline derivatives as p2x3 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2022534751A JP2022534751A (ja) | 2022-08-03 |
| JPWO2020239952A5 true JPWO2020239952A5 (enExample) | 2023-06-05 |
| JP7641917B2 JP7641917B2 (ja) | 2025-03-07 |
Family
ID=70861506
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021570931A Active JP7641917B2 (ja) | 2019-05-31 | 2020-05-28 | Ｐ２ｘ３阻害剤としてのアミノキナゾリン誘導体 |
| JP2021570930A Active JP7644029B2 (ja) | 2019-05-31 | 2020-05-28 | Ｐ２ｘ３阻害剤としてのアミノキナゾリン誘導体 |
| JP2025029719A Pending JP2025098014A (ja) | 2019-05-31 | 2025-02-27 | Ｐ２ｘ３阻害剤としてのアミノキナゾリン誘導体 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2021570930A Active JP7644029B2 (ja) | 2019-05-31 | 2020-05-28 | Ｐ２ｘ３阻害剤としてのアミノキナゾリン誘導体 |
| JP2025029719A Pending JP2025098014A (ja) | 2019-05-31 | 2025-02-27 | Ｐ２ｘ３阻害剤としてのアミノキナゾリン誘導体 |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US20230092892A1 (enExample) |
| EP (2) | EP3976180A1 (enExample) |
| JP (3) | JP7641917B2 (enExample) |
| KR (2) | KR20220016499A (enExample) |
| CN (3) | CN113891745B (enExample) |
| AU (2) | AU2020281923A1 (enExample) |
| BR (2) | BR112021022099A2 (enExample) |
| CA (2) | CA3139019A1 (enExample) |
| CL (1) | CL2021003165A1 (enExample) |
| CO (1) | CO2021017031A2 (enExample) |
| GE (2) | GEP20257823B (enExample) |
| IL (1) | IL288405A (enExample) |
| MA (2) | MA56021A (enExample) |
| MX (2) | MX2021014113A (enExample) |
| PE (1) | PE20220934A1 (enExample) |
| PH (1) | PH12021552881A1 (enExample) |
| SA (1) | SA521430920B1 (enExample) |
| SG (1) | SG11202112187YA (enExample) |
| WO (2) | WO2020239952A1 (enExample) |
| ZA (1) | ZA202108273B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR112021022099A2 (pt) * | 2019-05-31 | 2021-12-28 | Chiesi Farm Spa | Derivados de amino quinazolina como inibidores de p2x3 |
| FI3976597T3 (fi) | 2019-05-31 | 2024-09-25 | Janssen Pharmaceutica Nv | Nf-kb:tä indusoivan kinaasin pienimolekyylisiä estäjiä |
| CA3141826A1 (en) | 2019-05-31 | 2020-12-03 | Ikena Oncology, Inc. | Tead inhibitors and uses thereof |
| BR112021020279A2 (pt) * | 2019-05-31 | 2021-12-14 | Chiesi Farm Spa | Derivados de piridopirimidinas como inibidores de p2x3 |
| WO2022063205A1 (zh) * | 2020-09-24 | 2022-03-31 | 中国医药研究开发中心有限公司 | 芳基甲酰胺类化合物及其制备方法和医药用途 |
| WO2022083657A1 (zh) * | 2020-10-20 | 2022-04-28 | 苏州泽璟生物制药股份有限公司 | 取代苯并或吡啶并嘧啶胺类抑制剂及其制备方法和应用 |
| ES3026782T3 (en) * | 2020-11-27 | 2025-06-12 | Chiesi Farm Spa | (aza)quinoline 4-amines derivatives as p2x3 inhibitors |
| AU2021388923A1 (en) * | 2020-11-27 | 2023-05-25 | Chiesi Farmaceutici S.P.A. | Amino quinazoline derivatives as p2x3 inhibitors |
| CN112661803A (zh) * | 2020-12-17 | 2021-04-16 | 上海药明康德新药开发有限公司 | DNA编码化合物库构建中On-DNA 4-胺基喹唑啉化合物的合成方法 |
| KR20230155422A (ko) * | 2020-12-22 | 2023-11-10 | 메카니스틱 테라퓨틱스 엘엘씨 | Egfr 및/또는 pi3k 억제제로서의 치환된 아미노벤질헤테로아릴 화합물 |
| WO2022171118A1 (zh) * | 2021-02-10 | 2022-08-18 | 石药集团中奇制药技术（石家庄）有限公司 | 一种具有抗肿瘤活性的化合物及其用途 |
| CN115677601B (zh) * | 2021-07-29 | 2025-06-03 | 石药集团中奇制药技术（石家庄）有限公司 | 一种具有抗肿瘤活性的化合物及其用途 |
| WO2024235225A1 (zh) * | 2023-05-15 | 2024-11-21 | 苏州泽璟生物制药股份有限公司 | 取代嘧啶并环类抑制剂及其制备方法和应用 |
| WO2024240728A1 (en) | 2023-05-22 | 2024-11-28 | Chiesi Farmaceutici S.P.A. | Process and intermediates for the preparation of a p2x3 inhibitor |
| AR132741A1 (es) | 2023-05-22 | 2025-07-23 | Chiesi Farm Spa | Sales de derivados de aminoquinazolina |
| WO2025101598A1 (en) * | 2023-11-07 | 2025-05-15 | Zeno Management, Inc. | Bi-cyclic pyrimidine compounds, methods and uses thereof |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PH31122A (en) | 1993-03-31 | 1998-02-23 | Eisai Co Ltd | Nitrogen-containing fused-heterocycle compounds. |
| JP4342007B2 (ja) | 1998-08-10 | 2009-10-14 | 大日本住友製薬株式会社 | キナゾリン誘導体 |
| BR122018003623B8 (pt) * | 2004-03-05 | 2021-07-27 | Hoffmann La Roche | diaminopirimidinas, seus usos, e composição farmacêutica |
| ATE537169T1 (de) * | 2005-08-15 | 2011-12-15 | Hoffmann La Roche | Piperidin- und piperazinderivate als p2x3- antagonisten |
| WO2007025925A1 (en) | 2005-09-01 | 2007-03-08 | F. Hoffmann-La Roche Ag | Diaminopyrimidines as p2x3 and p2x2/3 modulators |
| WO2008000645A1 (en) | 2006-06-29 | 2008-01-03 | F. Hoffmann-La Roche Ag | Tetrazole-substituted arylamides |
| CA2682162C (en) | 2007-04-02 | 2016-05-10 | Renovis, Inc. | Pyrid-2-yl fused heterocyclic compounds, and compositions and uses thereof |
| PL2139334T3 (pl) | 2007-04-17 | 2013-11-29 | Evotec Ag | Skondensowane związki heterocykliczne 2-cyjanofenylu i ich kompozycje i zastosowania |
| MX2010009561A (es) | 2008-02-29 | 2010-09-24 | Renovis Inc | Compuestos amida, composiciones y usos de los mismos. |
| JP5608655B2 (ja) | 2008-09-18 | 2014-10-15 | エヴォテック アーゲー | Ｐ２ｘ３受容体活性のモジュレーター |
| AU2011326427B2 (en) | 2010-11-10 | 2016-01-07 | Infinity Pharmaceuticals Inc. | Heterocyclic compounds and uses thereof |
| WO2014102233A1 (en) | 2012-12-27 | 2014-07-03 | F. Hoffmann-La Roche Ag | Comt inhibitors |
| TWI637949B (zh) | 2013-06-14 | 2018-10-11 | 塩野義製藥股份有限公司 | 胺基三衍生物及含有其等之醫藥組合物 |
| US20170239249A1 (en) * | 2014-09-30 | 2017-08-24 | Bristol-Myers Squibb Company | Quinazoline-based kinase inhibitors |
| JPWO2016084922A1 (ja) | 2014-11-28 | 2017-09-07 | 塩野義製薬株式会社 | １，２，４−トリアジン誘導体およびその医薬組成物 |
| JPWO2016088838A1 (ja) | 2014-12-04 | 2017-09-14 | 塩野義製薬株式会社 | プリン誘導体およびその医薬組成物 |
| RS63014B1 (sr) | 2014-12-09 | 2022-04-29 | Bayer Ag | 1,3-tiazol-2-il supstituisani benzamidi |
| WO2017011729A1 (en) | 2015-07-16 | 2017-01-19 | Patara Pharma, LLC | Combination therapies for the treatment of lung diseases |
| LT3355889T (lt) | 2015-09-29 | 2023-05-10 | Afferent Pharmaceuticals Inc. | Diaminopirimidino p2x3 ir p2x2/3 receptorių moduliatoriai, skirti panaudoti gydant kosulį |
| JP6882289B2 (ja) * | 2015-11-25 | 2021-06-02 | コンバージーン・リミテッド・ライアビリティ・カンパニーＣｏｎｖｅｒｇｅｎｅ Ｌｌｃ | 二環式ｂｅｔブロモドメイン阻害剤及びその使用 |
| ES2800339T3 (es) | 2016-06-30 | 2020-12-29 | Gilead Sciences Inc | 4,6-diaminoquinazolinas como moduladores de cuna y métodos de uso de los mismos |
| WO2018035061A1 (en) * | 2016-08-15 | 2018-02-22 | Neupharma, Inc. | Certain chemical entities, compositions, and methods |
| US10898487B2 (en) * | 2016-12-22 | 2021-01-26 | Boehringer Ingelheim International Gmbh | Benzylamino substituted quinazolines and derivatives as SOS1 inhibitors |
| GB201700814D0 (en) | 2017-01-17 | 2017-03-01 | Liverpool School Tropical Medicine | Compounds |
| EP3619193B1 (en) * | 2017-05-05 | 2023-03-22 | Hepanova, Inc. | Amino-aryl-benzamide compounds and methods of use thereof |
| BR112021020279A2 (pt) | 2019-05-31 | 2021-12-14 | Chiesi Farm Spa | Derivados de piridopirimidinas como inibidores de p2x3 |
| BR112021022099A2 (pt) * | 2019-05-31 | 2021-12-28 | Chiesi Farm Spa | Derivados de amino quinazolina como inibidores de p2x3 |
-
2020
- 2020-05-28 BR BR112021022099A patent/BR112021022099A2/pt unknown
- 2020-05-28 AU AU2020281923A patent/AU2020281923A1/en active Pending
- 2020-05-28 MA MA056021A patent/MA56021A/fr unknown
- 2020-05-28 CN CN202080039837.0A patent/CN113891745B/zh active Active
- 2020-05-28 KR KR1020217043074A patent/KR20220016499A/ko active Pending
- 2020-05-28 CA CA3139019A patent/CA3139019A1/en active Pending
- 2020-05-28 AU AU2020285336A patent/AU2020285336A1/en active Pending
- 2020-05-28 US US17/615,056 patent/US20230092892A1/en active Pending
- 2020-05-28 JP JP2021570931A patent/JP7641917B2/ja active Active
- 2020-05-28 MX MX2021014113A patent/MX2021014113A/es unknown
- 2020-05-28 CN CN202410508911.9A patent/CN118239931A/zh active Pending
- 2020-05-28 SG SG11202112187YA patent/SG11202112187YA/en unknown
- 2020-05-28 KR KR1020217043072A patent/KR20220016498A/ko active Pending
- 2020-05-28 PH PH1/2021/552881A patent/PH12021552881A1/en unknown
- 2020-05-28 WO PCT/EP2020/064914 patent/WO2020239952A1/en not_active Ceased
- 2020-05-28 EP EP20728766.5A patent/EP3976180A1/en active Pending
- 2020-05-28 CA CA3139018A patent/CA3139018A1/en active Pending
- 2020-05-28 CN CN202080040266.2A patent/CN114269432B/zh active Active
- 2020-05-28 EP EP20728765.7A patent/EP3976179A1/en active Pending
- 2020-05-28 US US17/615,017 patent/US12466820B2/en active Active
- 2020-05-28 BR BR112021021738A patent/BR112021021738A2/pt unknown
- 2020-05-28 MA MA056022A patent/MA56022A/fr unknown
- 2020-05-28 GE GEAP202015818A patent/GEP20257823B/en unknown
- 2020-05-28 WO PCT/EP2020/064913 patent/WO2020239951A1/en not_active Ceased
- 2020-05-28 JP JP2021570930A patent/JP7644029B2/ja active Active
- 2020-05-28 GE GEAP202515818A patent/GEAP202515818A/en unknown
- 2020-05-28 PE PE2021001962A patent/PE20220934A1/es unknown
- 2020-05-28 MX MX2021014115A patent/MX2021014115A/es unknown
-
2021
- 2021-10-26 ZA ZA2021/08273A patent/ZA202108273B/en unknown
- 2021-11-22 SA SA521430920A patent/SA521430920B1/ar unknown
- 2021-11-25 IL IL288405A patent/IL288405A/en unknown
- 2021-11-29 CL CL2021003165A patent/CL2021003165A1/es unknown
- 2021-12-14 CO CONC2021/0017031A patent/CO2021017031A2/es unknown
-
2025
- 2025-02-27 JP JP2025029719A patent/JP2025098014A/ja active Pending