JP5325105B2 - ヤヌスキナーゼ阻害剤として有用なベンゾオキサゾールおよびオキサゾロピリジン - Google Patents
ヤヌスキナーゼ阻害剤として有用なベンゾオキサゾールおよびオキサゾロピリジン Download PDFInfo
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- JP5325105B2 JP5325105B2 JP2009527741A JP2009527741A JP5325105B2 JP 5325105 B2 JP5325105 B2 JP 5325105B2 JP 2009527741 A JP2009527741 A JP 2009527741A JP 2009527741 A JP2009527741 A JP 2009527741A JP 5325105 B2 JP5325105 B2 JP 5325105B2
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- JP
- Japan
- Prior art keywords
- phenyl
- methyl
- benzoxazol
- piperazin
- ylmethyl
- Prior art date
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- BFPLMTPHDFFMTG-UHFFFAOYSA-N [1,3]oxazolo[5,4-b]pyridine Chemical compound C1=CN=C2OC=NC2=C1 BFPLMTPHDFFMTG-UHFFFAOYSA-N 0.000 title description 3
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 title 1
- 229940122245 Janus kinase inhibitor Drugs 0.000 title 1
- -1 2,7-disubstituted benzoxazole Chemical class 0.000 claims abstract description 619
- 150000001875 compounds Chemical class 0.000 claims abstract description 299
- 150000003839 salts Chemical class 0.000 claims abstract description 57
- 238000000034 method Methods 0.000 claims abstract description 44
- 238000011282 treatment Methods 0.000 claims abstract description 39
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 230000008569 process Effects 0.000 claims abstract description 12
- 241001465754 Metazoa Species 0.000 claims abstract description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 89
- 229910052717 sulfur Inorganic materials 0.000 claims description 49
- 125000003944 tolyl group Chemical group 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 11
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 9
- UXBVFVGUHFXBEC-UHFFFAOYSA-N 7-(4-aminophenyl)-n-(3,4,5-trimethoxyphenyl)-1,3-benzoxazol-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=CC(N)=CC=4)C=CC=C3N=2)=C1 UXBVFVGUHFXBEC-UHFFFAOYSA-N 0.000 claims description 7
- HTLBXUGTQSCOCA-UHFFFAOYSA-N 7-[4-(aminomethyl)phenyl]-n-(3,4,5-trimethoxyphenyl)-1,3-benzoxazol-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=CC(CN)=CC=4)C=CC=C3N=2)=C1 HTLBXUGTQSCOCA-UHFFFAOYSA-N 0.000 claims description 7
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 5
- MVSZRYMPBVTTJZ-UHFFFAOYSA-N 4-[2-(3,4,5-trimethoxyanilino)-1,3-benzoxazol-7-yl]benzonitrile Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=CC(=CC=4)C#N)C=CC=C3N=2)=C1 MVSZRYMPBVTTJZ-UHFFFAOYSA-N 0.000 claims description 5
- JBLDCINMLPLRMR-UHFFFAOYSA-N 7-(3-aminophenyl)-n-(3,4,5-trimethoxyphenyl)-1,3-benzoxazol-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=C(N)C=CC=4)C=CC=C3N=2)=C1 JBLDCINMLPLRMR-UHFFFAOYSA-N 0.000 claims description 5
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 5
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 5
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 5
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000001680 trimethoxyphenyl group Chemical group 0.000 claims description 5
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 4
- XKEGANFLPSLKLA-UHFFFAOYSA-N 2-methoxy-n,n-dimethyl-4-[[7-[4-(morpholine-4-carbonyl)phenyl]-1,3-benzoxazol-2-yl]amino]benzamide Chemical compound C1=C(C(=O)N(C)C)C(OC)=CC(NC=2OC3=C(C=4C=CC(=CC=4)C(=O)N4CCOCC4)C=CC=C3N=2)=C1 XKEGANFLPSLKLA-UHFFFAOYSA-N 0.000 claims description 3
- MWYPYFVFRTZEIL-UHFFFAOYSA-N 7-[4-[(4-methylpiperazin-1-yl)methyl]phenyl]-n-(3,4,5-trimethoxyphenyl)-1,3-benzoxazol-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=CC(CN5CCN(C)CC5)=CC=4)C=CC=C3N=2)=C1 MWYPYFVFRTZEIL-UHFFFAOYSA-N 0.000 claims description 3
- 238000006619 Stille reaction Methods 0.000 claims description 3
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 3
- JBQRUSKLKTYFHS-UHFFFAOYSA-N [4-[2-(3,4,5-trimethoxyanilino)-1,3-benzoxazol-7-yl]phenyl]methanol Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=CC(CO)=CC=4)C=CC=C3N=2)=C1 JBQRUSKLKTYFHS-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- ZUIVNYCUKBVSNF-UHFFFAOYSA-N (4-methylpiperazin-1-yl)-[4-[2-(3,4,5-trimethoxyanilino)-1,3-benzoxazol-7-yl]phenyl]methanone Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=CC(=CC=4)C(=O)N4CCN(C)CC4)C=CC=C3N=2)=C1 ZUIVNYCUKBVSNF-UHFFFAOYSA-N 0.000 claims description 2
- LQCQFEJUBMGYFX-UHFFFAOYSA-N 1-[4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-1,3-benzoxazol-2-yl]amino]phenyl]pyrrolidin-2-one Chemical compound FC1=CC(C=2C=3OC(NC=4C=CC(=CC=4)N4C(CCC4)=O)=NC=3C=CC=2)=CC(F)=C1CN1CCOCC1 LQCQFEJUBMGYFX-UHFFFAOYSA-N 0.000 claims description 2
- JHVGJLJVIUEVSL-UHFFFAOYSA-N 1-morpholin-4-yl-2-[4-[2-(3,4,5-trimethoxyanilino)-1,3-benzoxazol-7-yl]phenyl]ethanone Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=CC(CC(=O)N5CCOCC5)=CC=4)C=CC=C3N=2)=C1 JHVGJLJVIUEVSL-UHFFFAOYSA-N 0.000 claims description 2
- PUVPBQQCYCNAEX-UHFFFAOYSA-N 2-[2-fluoro-4-[2-[3-methyl-4-(4-methylpiperazine-1-carbonyl)anilino]-1,3-benzoxazol-7-yl]phenyl]-1-morpholin-4-ylethanone Chemical compound C1CN(C)CCN1C(=O)C(C(=C1)C)=CC=C1NC1=NC2=CC=CC(C=3C=C(F)C(CC(=O)N4CCOCC4)=CC=3)=C2O1 PUVPBQQCYCNAEX-UHFFFAOYSA-N 0.000 claims description 2
- QVTYETFFDAYZJM-UHFFFAOYSA-N 2-[4-[2-(4-methylsulfinylanilino)-1,3-benzoxazol-7-yl]phenyl]-1-morpholin-4-ylethanone Chemical compound C1=CC(S(=O)C)=CC=C1NC1=NC2=CC=CC(C=3C=CC(CC(=O)N4CCOCC4)=CC=3)=C2O1 QVTYETFFDAYZJM-UHFFFAOYSA-N 0.000 claims description 2
- IKUNUNXHVKIZEG-UHFFFAOYSA-N 2-[4-[2-(4-methylsulfonylanilino)-1,3-benzoxazol-7-yl]phenyl]-1-morpholin-4-ylethanone Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NC1=NC2=CC=CC(C=3C=CC(CC(=O)N4CCOCC4)=CC=3)=C2O1 IKUNUNXHVKIZEG-UHFFFAOYSA-N 0.000 claims description 2
- HNCAURUDDZEXDN-UHFFFAOYSA-N 2-[4-[2-[3-methyl-4-(4-methylpiperazine-1-carbonyl)anilino]-1,3-benzoxazol-7-yl]phenyl]-1-morpholin-4-ylethanone Chemical compound C1CN(C)CCN1C(=O)C(C(=C1)C)=CC=C1NC1=NC2=CC=CC(C=3C=CC(CC(=O)N4CCOCC4)=CC=3)=C2O1 HNCAURUDDZEXDN-UHFFFAOYSA-N 0.000 claims description 2
- DUHXZLNOTMJPAF-UHFFFAOYSA-N 2-[4-[2-[4-(4-cyclopropylpiperazin-1-yl)-3-methylanilino]-1,3-benzoxazol-7-yl]phenyl]-2-methyl-1-morpholin-4-ylpropan-1-one Chemical compound C=1C=C(N2CCN(CC2)C2CC2)C(C)=CC=1NC(OC1=2)=NC1=CC=CC=2C(C=C1)=CC=C1C(C)(C)C(=O)N1CCOCC1 DUHXZLNOTMJPAF-UHFFFAOYSA-N 0.000 claims description 2
- XBFCPYYBUZVREP-UHFFFAOYSA-N 2-[4-[2-[4-(4-ethylpiperazin-1-yl)-3-methylanilino]-1,3-benzoxazol-7-yl]phenyl]-2-methyl-1-morpholin-4-ylpropan-1-one Chemical compound C1CN(CC)CCN1C(C(=C1)C)=CC=C1NC1=NC2=CC=CC(C=3C=CC(=CC=3)C(C)(C)C(=O)N3CCOCC3)=C2O1 XBFCPYYBUZVREP-UHFFFAOYSA-N 0.000 claims description 2
- BGUWIPOUDHQJQW-UHFFFAOYSA-N 2-[4-[2-[4-(4-methylpiperazin-1-yl)anilino]-1,3-benzoxazol-7-yl]phenyl]-1-morpholin-4-ylethanone Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC2=CC=CC(C=3C=CC(CC(=O)N4CCOCC4)=CC=3)=C2O1 BGUWIPOUDHQJQW-UHFFFAOYSA-N 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- KMIYVKBDTPNEMG-UHFFFAOYSA-N 2-methyl-2-[4-[2-[4-(4-methylpiperazin-1-yl)anilino]-1,3-benzoxazol-7-yl]phenyl]-1-morpholin-4-ylpropan-1-one Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC2=CC=CC(C=3C=CC(=CC=3)C(C)(C)C(=O)N3CCOCC3)=C2O1 KMIYVKBDTPNEMG-UHFFFAOYSA-N 0.000 claims description 2
- FZPOSFMWXAMKTA-UHFFFAOYSA-N 3-[2-(3,4,5-trimethoxyanilino)-1,3-benzoxazol-7-yl]benzamide Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=C(C=CC=4)C(N)=O)C=CC=C3N=2)=C1 FZPOSFMWXAMKTA-UHFFFAOYSA-N 0.000 claims description 2
- PJOFYYPCCAJWNW-UHFFFAOYSA-N 3-[2-(3,4,5-trimethoxyanilino)-1,3-benzoxazol-7-yl]benzonitrile Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=C(C=CC=4)C#N)C=CC=C3N=2)=C1 PJOFYYPCCAJWNW-UHFFFAOYSA-N 0.000 claims description 2
- ANLLJVNQONWMDM-UHFFFAOYSA-N 3-[2-(3,4,5-trimethoxyanilino)-1,3-benzoxazol-7-yl]phenol Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=C(O)C=CC=4)C=CC=C3N=2)=C1 ANLLJVNQONWMDM-UHFFFAOYSA-N 0.000 claims description 2
- ZIZRNDYTHZUJMX-UHFFFAOYSA-N 4-(3-aminophenyl)-n-(3,4,5-trimethoxyphenyl)-[1,3]oxazolo[5,4-c]pyridin-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=C(N)C=CC=4)N=CC=C3N=2)=C1 ZIZRNDYTHZUJMX-UHFFFAOYSA-N 0.000 claims description 2
- PVBXASBYRQNIRT-UHFFFAOYSA-N 4-(4-aminophenyl)-n-(3,4,5-trimethoxyphenyl)-[1,3]oxazolo[5,4-c]pyridin-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=CC(N)=CC=4)N=CC=C3N=2)=C1 PVBXASBYRQNIRT-UHFFFAOYSA-N 0.000 claims description 2
- RPLKUFKLZRTRTQ-UHFFFAOYSA-N 4-[2-(3,4,5-trimethoxyanilino)-1,3-benzoxazol-7-yl]benzamide Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=CC(=CC=4)C(N)=O)C=CC=C3N=2)=C1 RPLKUFKLZRTRTQ-UHFFFAOYSA-N 0.000 claims description 2
- BMPHAHMCRHCVSY-UHFFFAOYSA-N 4-[2-(3,4,5-trimethoxyanilino)-1,3-benzoxazol-7-yl]benzenesulfonamide Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=CC(=CC=4)S(N)(=O)=O)C=CC=C3N=2)=C1 BMPHAHMCRHCVSY-UHFFFAOYSA-N 0.000 claims description 2
- YJMFGGLNEHFURZ-UHFFFAOYSA-N 4-[2-(3,4,5-trimethoxyanilino)-[1,3]oxazolo[5,4-c]pyridin-4-yl]benzenesulfonamide Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=CC(=CC=4)S(N)(=O)=O)N=CC=C3N=2)=C1 YJMFGGLNEHFURZ-UHFFFAOYSA-N 0.000 claims description 2
- ZQEYKJQBHCZAIQ-UHFFFAOYSA-N 4-[2-(3,4-dimethoxyanilino)-1,3-benzoxazol-7-yl]-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1C1=CC=CC2=C1OC(NC=1C=C(OC)C(OC)=CC=1)=N2 ZQEYKJQBHCZAIQ-UHFFFAOYSA-N 0.000 claims description 2
- GIBUNVJRGDFUPJ-UHFFFAOYSA-N 4-[2-(3,4-dimethoxyanilino)-1,3-benzoxazol-7-yl]benzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1NC1=NC2=CC=CC(C=3C=CC(=CC=3)S(N)(=O)=O)=C2O1 GIBUNVJRGDFUPJ-UHFFFAOYSA-N 0.000 claims description 2
- XJEFTKVWSHBXCF-UHFFFAOYSA-N 4-[2-(3,5-dimethoxyanilino)-1,3-benzoxazol-7-yl]benzenesulfonamide Chemical compound COC1=CC(OC)=CC(NC=2OC3=C(C=4C=CC(=CC=4)S(N)(=O)=O)C=CC=C3N=2)=C1 XJEFTKVWSHBXCF-UHFFFAOYSA-N 0.000 claims description 2
- LBDPJJPWBXECKH-UHFFFAOYSA-N 4-[2-(3-methoxy-4-methylanilino)-1,3-benzoxazol-7-yl]-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1C1=CC=CC2=C1OC(NC=1C=C(OC)C(C)=CC=1)=N2 LBDPJJPWBXECKH-UHFFFAOYSA-N 0.000 claims description 2
- FBBKHZHSVDHEPC-UHFFFAOYSA-N 4-[2-(4-methoxyanilino)-1,3-benzoxazol-7-yl]-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1C1=CC=CC2=C1OC(NC=1C=CC(OC)=CC=1)=N2 FBBKHZHSVDHEPC-UHFFFAOYSA-N 0.000 claims description 2
- CNPSHGJTABUFCO-UHFFFAOYSA-N 4-[2-[4-(4-ethylpiperazin-1-yl)-3-methylanilino]-1,3-benzoxazol-7-yl]benzenesulfonamide Chemical compound C1CN(CC)CCN1C(C(=C1)C)=CC=C1NC1=NC2=CC=CC(C=3C=CC(=CC=3)S(N)(=O)=O)=C2O1 CNPSHGJTABUFCO-UHFFFAOYSA-N 0.000 claims description 2
- RWVMAEJTWJRDEA-UHFFFAOYSA-N 4-[2-[4-(4-methylpiperazin-1-yl)anilino]-1,3-benzoxazol-7-yl]benzenesulfonamide Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NC2=CC=CC(C=3C=CC(=CC=3)S(N)(=O)=O)=C2O1 RWVMAEJTWJRDEA-UHFFFAOYSA-N 0.000 claims description 2
- KPVLNGQQGXRVLS-UHFFFAOYSA-N 4-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-n-[4-(4-ethylpiperazin-1-yl)-3-methylphenyl]-[1,3]oxazolo[5,4-c]pyridin-2-amine Chemical compound C1CN(CC)CCN1C(C(=C1)C)=CC=C1NC1=NC2=CC=NC(C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)=C2O1 KPVLNGQQGXRVLS-UHFFFAOYSA-N 0.000 claims description 2
- ZWLOUUJFBZLECC-UHFFFAOYSA-N 4-[[7-[2-fluoro-4-(morpholine-4-carbonyl)phenyl]-1,3-benzoxazol-2-yl]amino]-n,n,2-trimethylbenzamide Chemical compound C1=C(C)C(C(=O)N(C)C)=CC=C1NC1=NC2=CC=CC(C=3C(=CC(=CC=3)C(=O)N3CCOCC3)F)=C2O1 ZWLOUUJFBZLECC-UHFFFAOYSA-N 0.000 claims description 2
- JPVQJSNRDPPJID-UHFFFAOYSA-N 4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-1,3-benzoxazol-2-yl]amino]-n,2-dimethylbenzamide Chemical compound C1=C(C)C(C(=O)NC)=CC=C1NC1=NC2=CC=CC(C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)=C2O1 JPVQJSNRDPPJID-UHFFFAOYSA-N 0.000 claims description 2
- MBBPTMKXDHVDSS-UHFFFAOYSA-N 4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-1,3-benzoxazol-2-yl]amino]-n,n,2-trimethylbenzamide Chemical compound C1=C(C)C(C(=O)N(C)C)=CC=C1NC1=NC2=CC=CC(C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)=C2O1 MBBPTMKXDHVDSS-UHFFFAOYSA-N 0.000 claims description 2
- WPODTHCWPDTNCY-UHFFFAOYSA-N 4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-1,3-benzoxazol-2-yl]amino]-n,n-diethyl-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)N(CC)CC)=CC=C1NC1=NC2=CC=CC(C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)=C2O1 WPODTHCWPDTNCY-UHFFFAOYSA-N 0.000 claims description 2
- GJXXAFDGVPNZCS-UHFFFAOYSA-N 4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-1,3-benzoxazol-2-yl]amino]-n-[2-(dimethylamino)ethyl]-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)NCCN(C)C)=CC=C1NC1=NC2=CC=CC(C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)=C2O1 GJXXAFDGVPNZCS-UHFFFAOYSA-N 0.000 claims description 2
- NCWLZRGHZVTXHW-UHFFFAOYSA-N 4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-1,3-benzoxazol-2-yl]amino]-n-[2-(dimethylamino)ethyl]-n,2-dimethylbenzamide Chemical compound C1=C(C)C(C(=O)N(C)CCN(C)C)=CC=C1NC1=NC2=CC=CC(C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)=C2O1 NCWLZRGHZVTXHW-UHFFFAOYSA-N 0.000 claims description 2
- GUFDLBOQMBNMJW-UHFFFAOYSA-N 4-[[7-[3-fluoro-4-(morpholin-4-ylmethyl)phenyl]-1,3-benzoxazol-2-yl]amino]-n,n,2-trimethylbenzamide Chemical compound C1=C(C)C(C(=O)N(C)C)=CC=C1NC1=NC2=CC=CC(C=3C=C(F)C(CN4CCOCC4)=CC=3)=C2O1 GUFDLBOQMBNMJW-UHFFFAOYSA-N 0.000 claims description 2
- LNAZRCWOQJRGCJ-UHFFFAOYSA-N 4-[[7-[3-fluoro-4-(morpholine-4-carbonyl)phenyl]-1,3-benzoxazol-2-yl]amino]-n,n,2-trimethylbenzamide Chemical compound C1=C(C)C(C(=O)N(C)C)=CC=C1NC1=NC2=CC=CC(C=3C=C(F)C(C(=O)N4CCOCC4)=CC=3)=C2O1 LNAZRCWOQJRGCJ-UHFFFAOYSA-N 0.000 claims description 2
- NEUJWTIUYWKVBE-UHFFFAOYSA-N 4-[[7-[4-[(1,1-dioxo-1,4-thiazinan-4-yl)methyl]-3,5-difluorophenyl]-1,3-benzoxazol-2-yl]amino]-n,n,2-trimethylbenzamide Chemical compound C1=C(C)C(C(=O)N(C)C)=CC=C1NC1=NC2=CC=CC(C=3C=C(F)C(CN4CCS(=O)(=O)CC4)=C(F)C=3)=C2O1 NEUJWTIUYWKVBE-UHFFFAOYSA-N 0.000 claims description 2
- YYUAURIHUBEGHX-UHFFFAOYSA-N 4-[[7-[4-[(4-acetylpiperazin-1-yl)methyl]-3,5-difluorophenyl]-1,3-benzoxazol-2-yl]amino]-n,n-diethyl-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)N(CC)CC)=CC=C1NC1=NC2=CC=CC(C=3C=C(F)C(CN4CCN(CC4)C(C)=O)=C(F)C=3)=C2O1 YYUAURIHUBEGHX-UHFFFAOYSA-N 0.000 claims description 2
- CRXZEWARUXDPKY-UHFFFAOYSA-N 5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-1,3-benzoxazol-2-yl]amino]-1,3-dihydroindol-2-one Chemical compound FC1=CC(C=2C=3OC(NC=4C=C5CC(=O)NC5=CC=4)=NC=3C=CC=2)=CC(F)=C1CN1CCOCC1 CRXZEWARUXDPKY-UHFFFAOYSA-N 0.000 claims description 2
- KRCKWPBJGJGULZ-UHFFFAOYSA-N 5-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-1,3-benzoxazol-2-yl]amino]-1,3-dimethylpyridin-2-one Chemical compound CN1C(=O)C(C)=CC(NC=2OC3=C(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC=C3N=2)=C1 KRCKWPBJGJGULZ-UHFFFAOYSA-N 0.000 claims description 2
- MWQLZCDAWNMJAP-UHFFFAOYSA-N 5-[[7-[3-fluoro-4-(morpholine-4-carbonyl)phenyl]-1,3-benzoxazol-2-yl]amino]-2-(4-methylpiperazin-1-yl)benzonitrile Chemical compound C1CN(C)CCN1C(C(=C1)C#N)=CC=C1NC1=NC2=CC=CC(C=3C=C(F)C(C(=O)N4CCOCC4)=CC=3)=C2O1 MWQLZCDAWNMJAP-UHFFFAOYSA-N 0.000 claims description 2
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- RGJMICFWNAVTAA-UHFFFAOYSA-N morpholin-4-yl-[4-[2-(3,4,5-trimethoxyanilino)-1,3-benzoxazol-7-yl]phenyl]methanone Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=CC(=CC=4)C(=O)N4CCOCC4)C=CC=C3N=2)=C1 RGJMICFWNAVTAA-UHFFFAOYSA-N 0.000 claims description 2
- ZLYZKPAQQZPPGP-UHFFFAOYSA-N n,n,2-trimethyl-4-[[7-[3-methyl-4-(morpholine-4-carbonyl)phenyl]-1,3-benzoxazol-2-yl]amino]benzamide Chemical compound C1=C(C)C(C(=O)N(C)C)=CC=C1NC1=NC2=CC=CC(C=3C=C(C)C(C(=O)N4CCOCC4)=CC=3)=C2O1 ZLYZKPAQQZPPGP-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
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- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
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Landscapes
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- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP06120733.8 | 2006-09-15 | ||
| EP06120733A EP1900729A1 (en) | 2006-09-15 | 2006-09-15 | Benzoxazoles and oxazolopyridines being useful as Janus kinases inhibitors |
| PCT/EP2007/007983 WO2008031594A1 (en) | 2006-09-15 | 2007-09-13 | Benzoxazoles and oxazolopyridines being useful as janus kinases inhibitors |
Publications (3)
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| JP2010503629A JP2010503629A (ja) | 2010-02-04 |
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| JP2009527741A Expired - Fee Related JP5325105B2 (ja) | 2006-09-15 | 2007-09-13 | ヤヌスキナーゼ阻害剤として有用なベンゾオキサゾールおよびオキサゾロピリジン |
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| GB2467670B (en) | 2007-10-04 | 2012-08-01 | Intellikine Inc | Chemical entities and therapeutic uses thereof |
| US8993580B2 (en) | 2008-03-14 | 2015-03-31 | Intellikine Llc | Benzothiazole kinase inhibitors and methods of use |
| BRPI0915231A2 (pt) | 2008-07-08 | 2018-06-12 | Intellikine Inc | compostos inibidores de quinase e métodos de uso |
| MX2011000211A (es) * | 2008-07-15 | 2011-03-03 | Sanofi Aventis | Oxazolopirimidinas como agonistas del receptor edg-1. |
| US20100041891A1 (en) * | 2008-08-12 | 2010-02-18 | Takeda Pharmaceutical Company Limited | Amide compound |
| US8476431B2 (en) | 2008-11-03 | 2013-07-02 | Itellikine LLC | Benzoxazole kinase inhibitors and methods of use |
| WO2010061971A1 (ja) | 2008-11-28 | 2010-06-03 | 興和株式会社 | ピリジン－３－カルボキシアミド誘導体 |
| WO2011078360A1 (ja) | 2009-12-24 | 2011-06-30 | 武田薬品工業株式会社 | アミド化合物 |
| TWI485153B (zh) * | 2010-01-13 | 2015-05-21 | Sanofi Aventis | ２，５，７－經取代唑并嘧啶衍生物 |
| US9295673B2 (en) | 2011-02-23 | 2016-03-29 | Intellikine Llc | Combination of mTOR inhibitors and P13-kinase inhibitors, and uses thereof |
| US8580816B2 (en) * | 2011-07-07 | 2013-11-12 | Sanofi | Carboxylic acid derivatives having an oxazolo[5,4-b]pyridine ring |
| US8907093B2 (en) * | 2011-07-07 | 2014-12-09 | Sanofi | Carboxylic acid derivatives having an oxazolo[4,5-c]pyridine ring |
| CN103102359B (zh) * | 2011-11-15 | 2016-11-09 | 江苏先声药业有限公司 | 嘧啶类化合物及其应用 |
| ES3018133T3 (en) | 2011-11-30 | 2025-05-14 | Univ Emory | Jak inhibitors for use in the prevention or treatment of a viral disease caused by a coronaviridae |
| WO2014075318A1 (zh) * | 2012-11-19 | 2014-05-22 | 江苏先声药业有限公司 | 嘧啶类化合物及其应用 |
| WO2014153509A1 (en) | 2013-03-22 | 2014-09-25 | Millennium Pharmaceuticals, Inc. | Combination of catalytic mtorc 1/2 inhibitors and selective inhibitors of aurora a kinase |
| CN103664759A (zh) * | 2013-12-06 | 2014-03-26 | 常熟市联创化学有限公司 | 一种3-羟基-2-硝基吡啶的制备方法 |
| WO2015117147A1 (en) | 2014-02-03 | 2015-08-06 | Quadriga Biosciences, Inc. | Beta-substituted beta-amino acids and analogs as chemotherapeutic agents |
| BR112016017993A2 (pt) | 2014-02-03 | 2017-08-08 | Quadriga Biosciences Inc | Gama-aminoácidos beta-substituídos e análogos como agentes quimioterapêuticos |
| WO2016047678A1 (ja) * | 2014-09-25 | 2016-03-31 | 武田薬品工業株式会社 | 複素環化合物 |
| KR20180035894A (ko) | 2015-08-03 | 2018-04-06 | 콰드리가 바이오사이언시스 인코포레이티드 | 화학치료제로서의 베타-치환된 베타-아미노산 및 유사체 및 이들의 용도 |
| US20220372135A1 (en) | 2019-09-27 | 2022-11-24 | Disc Medicine, Inc. | Methods for treating myelofibrosis and related conditions |
| KR20230012539A (ko) | 2020-05-13 | 2023-01-26 | 디스크 메디슨, 인크. | 골수섬유증을 치료하기 위한 항-헤모주벨린 (hjv) 항체 |
| WO2022251597A1 (en) | 2021-05-28 | 2022-12-01 | Verge Analytics, Inc. | Methods of treating neurological disorders with modulators of ribosomal protein s6 kinase alpha-1 (rsk1) and ribosomal protein s6 kinase alpha-3 (rsk2) |
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| DE60037345T2 (de) * | 1999-12-10 | 2008-11-13 | Pfizer Products Inc., Groton | Pyrrolo(2,3-d)pyrimidin-Verbindungen |
| SE0301373D0 (sv) * | 2003-05-09 | 2003-05-09 | Astrazeneca Ab | Novel compounds |
| DE10344223A1 (de) * | 2003-09-24 | 2005-04-21 | Merck Patent Gmbh | 1,3-Benzoxazolylderivate als Kinase-Inhibitoren |
| GB0402140D0 (en) * | 2004-01-30 | 2004-03-03 | Smithkline Beecham Corp | Novel compounds |
| EP1674467A1 (en) * | 2004-12-22 | 2006-06-28 | 4Sc Ag | 2,5- and 2,6-disubstituted benzazole derivatives useful as protein kinase inhibitors |
| CA2620127A1 (en) * | 2005-09-02 | 2007-03-08 | F. Hoffmann-La Roche Ag | Benzooxazole, oxazolopyridine, benzothiazole and thiazolopyridine derivatives |
| WO2008009458A1 (en) * | 2006-07-21 | 2008-01-24 | Novartis Ag | 2, 4 -di (arylaminio) -pyrimidine-5-carboxamide compounds as jak kinases inhibitors |
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