ES2377148T3 - Benzoxazoles y oxazolopiridinas útiles como inhibidores de las quinasas Janus - Google Patents
Benzoxazoles y oxazolopiridinas útiles como inhibidores de las quinasas Janus Download PDFInfo
- Publication number
- ES2377148T3 ES2377148T3 ES07802300T ES07802300T ES2377148T3 ES 2377148 T3 ES2377148 T3 ES 2377148T3 ES 07802300 T ES07802300 T ES 07802300T ES 07802300 T ES07802300 T ES 07802300T ES 2377148 T3 ES2377148 T3 ES 2377148T3
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- ES
- Spain
- Prior art keywords
- phenyl
- alkyl
- benzooxazol
- methyl
- piperazin
- 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.)
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- BFPLMTPHDFFMTG-UHFFFAOYSA-N [1,3]oxazolo[5,4-b]pyridine Chemical class C1=CN=C2OC=NC2=C1 BFPLMTPHDFFMTG-UHFFFAOYSA-N 0.000 title description 4
- 150000000183 1,3-benzoxazoles Chemical class 0.000 title description 2
- 229940122245 Janus kinase inhibitor Drugs 0.000 title description 2
- -1 cyano, hydroxyl Chemical group 0.000 claims abstract description 549
- 150000001875 compounds Chemical class 0.000 claims abstract description 318
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 113
- 150000003839 salts Chemical class 0.000 claims abstract description 65
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 51
- 239000001257 hydrogen Substances 0.000 claims abstract description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 28
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 19
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- JAXFYELIPVPBLH-UHFFFAOYSA-N 7-phenyl-n-piperidin-4-yl-1,3-benzoxazol-2-amine Chemical compound C1CNCCC1NC1=NC2=CC=CC(C=3C=CC=CC=3)=C2O1 JAXFYELIPVPBLH-UHFFFAOYSA-N 0.000 claims abstract description 10
- UMRYNCGEZWMEKD-UHFFFAOYSA-N n-[1-[(3,5-diethoxy-4-fluorophenyl)methyl]piperidin-4-yl]-7-phenyl-1,3-benzoxazol-2-amine Chemical compound CCOC1=C(F)C(OCC)=CC(CN2CCC(CC2)NC=2OC3=C(C=4C=CC=CC=4)C=CC=C3N=2)=C1 UMRYNCGEZWMEKD-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims abstract description 5
- 125000003944 tolyl group Chemical group 0.000 claims description 60
- 229910052717 sulfur Inorganic materials 0.000 claims description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 40
- 125000005843 halogen group Chemical group 0.000 claims description 36
- 238000011282 treatment Methods 0.000 claims description 35
- 125000001424 substituent group Chemical group 0.000 claims description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 201000010099 disease Diseases 0.000 claims description 25
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 24
- 108091000080 Phosphotransferase Proteins 0.000 claims description 23
- 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 claims description 23
- 102000020233 phosphotransferase Human genes 0.000 claims description 23
- 125000004076 pyridyl group Chemical group 0.000 claims description 22
- 125000001624 naphthyl group Chemical group 0.000 claims description 21
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 20
- 101000997832 Homo sapiens Tyrosine-protein kinase JAK2 Proteins 0.000 claims description 18
- 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000003814 drug Substances 0.000 claims description 16
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 13
- 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 claims description 11
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 11
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- 125000004802 cyanophenyl group Chemical group 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
- 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 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Chemical group 0.000 claims description 8
- 230000008569 process Effects 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 7
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 7
- 230000001404 mediated effect Effects 0.000 claims description 7
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 229940124597 therapeutic agent Drugs 0.000 claims description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000004230 chromenyl group Chemical group O1C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 4
- 125000001680 trimethoxyphenyl group Chemical group 0.000 claims description 4
- 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 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-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
- 125000000068 chlorophenyl group Chemical group 0.000 claims description 3
- 125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 3
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 3
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 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
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-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
- 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
- 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 2
- XEFRNCLPPFDWAC-UHFFFAOYSA-N 3,4,5-trimethoxyaniline Chemical compound COC1=CC(N)=CC(OC)=C1OC XEFRNCLPPFDWAC-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
- 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
- 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
- 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
- JZZKLCDTABRAHI-UHFFFAOYSA-N 4-[[4-[2-[4-(4-cyclopropylpiperazin-1-yl)-3-methylanilino]-1,3-benzoxazol-7-yl]-2,6-difluorophenyl]methyl]-1-methylpiperazin-2-one Chemical compound C1C(=O)N(C)CCN1CC1=C(F)C=C(C=2C=3OC(NC=4C=C(C)C(N5CCN(CC5)C5CC5)=CC=4)=NC=3C=CC=2)C=C1F JZZKLCDTABRAHI-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
- PPISUGAOFZSWMT-UHFFFAOYSA-N 4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-1,3-benzoxazol-2-yl]amino]-2-ethyl-n,n-dimethylbenzamide Chemical compound C1=C(C(=O)N(C)C)C(CC)=CC(NC=2OC3=C(C=4C=C(F)C(CN5CCOCC5)=C(F)C=4)C=CC=C3N=2)=C1 PPISUGAOFZSWMT-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
- SKOAILFDFRVQLU-UHFFFAOYSA-N 4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-1,3-benzoxazol-2-yl]amino]-n-(2-methoxyethyl)-n,2-dimethylbenzamide Chemical compound C1=C(C)C(C(=O)N(C)CCOC)=CC=C1NC1=NC2=CC=CC(C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)=C2O1 SKOAILFDFRVQLU-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
- CCYLXRZCCYTEPD-UHFFFAOYSA-N 4-[[7-[3,5-difluoro-4-(morpholin-4-ylmethyl)phenyl]-1,3-benzoxazol-2-yl]amino]-n-[3-(dimethylamino)propyl]-2-methylbenzamide Chemical compound C1=C(C)C(C(=O)NCCCN(C)C)=CC=C1NC1=NC2=CC=CC(C=3C=C(F)C(CN4CCOCC4)=C(F)C=3)=C2O1 CCYLXRZCCYTEPD-UHFFFAOYSA-N 0.000 claims description 2
- DXJFYTUABGHTNV-UHFFFAOYSA-N 4-[[7-[3,5-difluoro-4-[(3-oxopiperazin-1-yl)methyl]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(CN4CC(=O)NCC4)=C(F)C=3)=C2O1 DXJFYTUABGHTNV-UHFFFAOYSA-N 0.000 claims description 2
- FASUPNIUXSOUEZ-UHFFFAOYSA-N 4-[[7-[3,5-difluoro-4-[(4-methyl-3-oxopiperazin-1-yl)methyl]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(CN4CC(=O)N(C)CC4)=C(F)C=3)=C2O1 FASUPNIUXSOUEZ-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
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- XRTXYXCNVWUOKB-UHFFFAOYSA-N 7-(2-methoxyphenyl)-n-(3,4,5-trimethoxyphenyl)-1,3-benzoxazol-2-amine Chemical compound COC1=CC=CC=C1C1=CC=CC2=C1OC(NC=1C=C(OC)C(OC)=C(OC)C=1)=N2 XRTXYXCNVWUOKB-UHFFFAOYSA-N 0.000 claims description 2
- ROUGJNNRPQCIQZ-UHFFFAOYSA-N 7-(2-methylphenyl)-n-(3,4,5-trimethoxyphenyl)-1,3-benzoxazol-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C(=CC=CC=4)C)C=CC=C3N=2)=C1 ROUGJNNRPQCIQZ-UHFFFAOYSA-N 0.000 claims description 2
- BWVGAIJUWAPMNX-UHFFFAOYSA-N 7-(3-amino-4-chlorophenyl)-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(Cl)=CC=4)C=CC=C3N=2)=C1 BWVGAIJUWAPMNX-UHFFFAOYSA-N 0.000 claims description 2
- UURNNRNSXFXXHP-UHFFFAOYSA-N 7-(3-amino-4-methoxyphenyl)-n-(3,4,5-trimethoxyphenyl)-1,3-benzoxazol-2-amine Chemical compound C1=C(N)C(OC)=CC=C1C1=CC=CC2=C1OC(NC=1C=C(OC)C(OC)=C(OC)C=1)=N2 UURNNRNSXFXXHP-UHFFFAOYSA-N 0.000 claims description 2
- FZAGFNHIURVENH-UHFFFAOYSA-N 7-(3-chlorophenyl)-n-(3,4,5-trimethoxyphenyl)-1,3-benzoxazol-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=C(Cl)C=CC=4)C=CC=C3N=2)=C1 FZAGFNHIURVENH-UHFFFAOYSA-N 0.000 claims description 2
- FNTVDFNPNLGBOJ-UHFFFAOYSA-N 7-(3-methoxyphenyl)-n-(3,4,5-trimethoxyphenyl)-1,3-benzoxazol-2-amine Chemical compound COC1=CC=CC(C=2C=3OC(NC=4C=C(OC)C(OC)=C(OC)C=4)=NC=3C=CC=2)=C1 FNTVDFNPNLGBOJ-UHFFFAOYSA-N 0.000 claims description 2
- APGGPVMPCVNXNX-UHFFFAOYSA-N 7-(3-methoxyphenyl)-n-(4-morpholin-4-ylphenyl)-1,3-benzoxazol-2-amine Chemical compound COC1=CC=CC(C=2C=3OC(NC=4C=CC(=CC=4)N4CCOCC4)=NC=3C=CC=2)=C1 APGGPVMPCVNXNX-UHFFFAOYSA-N 0.000 claims description 2
- SEMGWBXKKAUDQJ-UHFFFAOYSA-N 7-(3-methylphenyl)-n-(3,4,5-trimethoxyphenyl)-1,3-benzoxazol-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=C(C)C=CC=4)C=CC=C3N=2)=C1 SEMGWBXKKAUDQJ-UHFFFAOYSA-N 0.000 claims description 2
- NQZMZJDDJJLQLK-UHFFFAOYSA-N 7-(3-methylsulfonylphenyl)-n-(3,4,5-trimethoxyphenyl)-1,3-benzoxazol-2-amine Chemical compound COC1=C(OC)C(OC)=CC(NC=2OC3=C(C=4C=C(C=CC=4)S(C)(=O)=O)C=CC=C3N=2)=C1 NQZMZJDDJJLQLK-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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- 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
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- 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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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- 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)
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| EP06120733 | 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 |
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| ES2377148T3 true ES2377148T3 (es) | 2012-03-22 |
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| ES07802300T Active ES2377148T3 (es) | 2006-09-15 | 2007-09-13 | Benzoxazoles y oxazolopiridinas útiles como inhibidores de las quinasas Janus |
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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 |
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| 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 |
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| BR112016017993A2 (pt) | 2014-02-03 | 2017-08-08 | Quadriga Biosciences Inc | Gama-aminoácidos beta-substituídos e análogos como agentes quimioterapêuticos |
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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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