ES2651349T3 - Composiciones y métodos para la inhibición de la ruta JAK - Google Patents
Composiciones y métodos para la inhibición de la ruta JAK Download PDFInfo
- Publication number
- ES2651349T3 ES2651349T3 ES06784727.7T ES06784727T ES2651349T3 ES 2651349 T3 ES2651349 T3 ES 2651349T3 ES 06784727 T ES06784727 T ES 06784727T ES 2651349 T3 ES2651349 T3 ES 2651349T3
- Authority
- ES
- Spain
- Prior art keywords
- pyrimidinediamine
- fluoro
- phenyl
- aminosulfonyl
- aminosulfonylphenyl
- 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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- 238000000034 method Methods 0.000 title claims description 7
- 230000002401 inhibitory effect Effects 0.000 title description 2
- 239000000203 mixture Substances 0.000 title 1
- -1 amino, aminocarbonyl Chemical group 0.000 claims abstract description 501
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 118
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 84
- HXCIDYGTACKSQQ-UHFFFAOYSA-N 5-fluoro-6-phenylpyrimidine-2,4-diamine Chemical compound NC1=NC(N)=C(F)C(C=2C=CC=CC=2)=N1 HXCIDYGTACKSQQ-UHFFFAOYSA-N 0.000 claims abstract description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 43
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims abstract description 29
- 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 abstract description 17
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 3
- FUVWRUJASRBHEK-UHFFFAOYSA-N 5-phenylpyrimidine-2,4-diamine Chemical compound NC1=NC(N)=NC=C1C1=CC=CC=C1 FUVWRUJASRBHEK-UHFFFAOYSA-N 0.000 claims description 19
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 14
- 159000000000 sodium salts Chemical class 0.000 claims description 13
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 12
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004458 methylaminocarbonyl group Chemical group [H]N(C(*)=O)C([H])([H])[H] 0.000 claims description 6
- GMMWNTHAIOJBSD-UHFFFAOYSA-N 6-chloro-4-n-(2,3-dimethylphenyl)-2-n,2-n-dimethylpyrimidine-2,4-diamine Chemical compound CN(C)C1=NC(Cl)=CC(NC=2C(=C(C)C=CC=2)C)=N1 GMMWNTHAIOJBSD-UHFFFAOYSA-N 0.000 claims description 5
- ADLPJXSNTYRFAI-UHFFFAOYSA-N 2-[4-[[5-fluoro-2-[3-(propanoylsulfamoyl)anilino]pyrimidin-4-yl]amino]phenyl]ethyl n,n-dimethylcarbamate Chemical compound CCC(=O)NS(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=CC(CCOC(=O)N(C)C)=CC=3)C(F)=CN=2)=C1 ADLPJXSNTYRFAI-UHFFFAOYSA-N 0.000 claims description 4
- YTLYLLTVENPWFT-UHFFFAOYSA-N 3-aminoprop-2-enoic acid Chemical group NC=CC(O)=O YTLYLLTVENPWFT-UHFFFAOYSA-N 0.000 claims description 4
- 210000001744 T-lymphocyte Anatomy 0.000 claims description 4
- HKNYUKDSEKARSG-UHFFFAOYSA-N n-[5-[[4-[4-(2-cyanoethyl)-3-methylanilino]-5-fluoropyrimidin-2-yl]amino]-2-methylphenyl]sulfonylpropanamide Chemical compound C1=C(C)C(S(=O)(=O)NC(=O)CC)=CC(NC=2N=C(NC=3C=C(C)C(CCC#N)=CC=3)C(F)=CN=2)=C1 HKNYUKDSEKARSG-UHFFFAOYSA-N 0.000 claims description 4
- CHQBVMBVYQAHES-UHFFFAOYSA-N 3-[[4-[[4-(cyanomethyl)-3-oxo-1,4-benzothiazin-6-yl]amino]-5-fluoropyrimidin-2-yl]amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=C4N(CC#N)C(=O)CSC4=CC=3)C(F)=CN=2)=C1 CHQBVMBVYQAHES-UHFFFAOYSA-N 0.000 claims description 3
- VSJPKSVDCDOVJB-UHFFFAOYSA-N 4-[[5-fluoro-4-[(2,2,4-trimethyl-1,1,3-trioxo-1$l^{6},4-benzothiazin-6-yl)amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=C2N(C)C(=O)C(C)(C)S(=O)(=O)C2=CC=C1NC(C(=CN=1)F)=NC=1NC1=CC=C(S(N)(=O)=O)C=C1 VSJPKSVDCDOVJB-UHFFFAOYSA-N 0.000 claims description 3
- SOKJMSBSBGDGIG-UHFFFAOYSA-N 5-[[5-fluoro-4-[(3-oxo-4h-1,4-benzothiazin-6-yl)amino]pyrimidin-2-yl]amino]-2-methylbenzenesulfonamide Chemical compound C1=C(S(N)(=O)=O)C(C)=CC=C1NC1=NC=C(F)C(NC=2C=C3NC(=O)CSC3=CC=2)=N1 SOKJMSBSBGDGIG-UHFFFAOYSA-N 0.000 claims description 3
- UTUUAIPSQMYOEQ-UHFFFAOYSA-N 5-[[5-fluoro-4-[[3-oxo-4-(pyridin-2-ylmethyl)-1,4-benzoxazin-6-yl]amino]pyrimidin-2-yl]amino]-2-methylbenzenesulfonamide Chemical compound C1=C(S(N)(=O)=O)C(C)=CC=C1NC1=NC=C(F)C(NC=2C=C3N(CC=4N=CC=CC=4)C(=O)COC3=CC=2)=N1 UTUUAIPSQMYOEQ-UHFFFAOYSA-N 0.000 claims description 3
- 229960003444 immunosuppressant agent Drugs 0.000 claims description 3
- 230000001861 immunosuppressant effect Effects 0.000 claims description 3
- 239000003018 immunosuppressive agent Substances 0.000 claims description 3
- DEODYXOEQQKAQB-UHFFFAOYSA-N 2-[2-chloro-4-[[5-fluoro-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]phenoxy]-n,n-dimethylacetamide Chemical compound C1=C(Cl)C(OCC(=O)N(C)C)=CC=C1NC1=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=C1F DEODYXOEQQKAQB-UHFFFAOYSA-N 0.000 claims description 2
- ZFSPAWFQNPWUJO-UHFFFAOYSA-N 2-[2-chloro-4-[[5-fluoro-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]phenoxy]-n-methylacetamide Chemical compound C1=C(Cl)C(OCC(=O)NC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=C1F ZFSPAWFQNPWUJO-UHFFFAOYSA-N 0.000 claims description 2
- BMVVDJQCGBKYHI-UHFFFAOYSA-N 2-[2-chloro-4-[[5-fluoro-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]phenoxy]acetamide Chemical compound C1=C(Cl)C(OCC(=O)N)=CC=C1NC1=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=C1F BMVVDJQCGBKYHI-UHFFFAOYSA-N 0.000 claims description 2
- OJRWJMADJBXUHN-UHFFFAOYSA-N 2-[2-chloro-4-[[5-methyl-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]phenoxy]-n,n-dimethylacetamide Chemical compound C1=C(Cl)C(OCC(=O)N(C)C)=CC=C1NC1=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=C1C OJRWJMADJBXUHN-UHFFFAOYSA-N 0.000 claims description 2
- RFNYPHNLDVTBGE-UHFFFAOYSA-N 2-[2-chloro-4-[[5-methyl-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]phenoxy]-n-methylacetamide Chemical compound C1=C(Cl)C(OCC(=O)NC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=C1C RFNYPHNLDVTBGE-UHFFFAOYSA-N 0.000 claims description 2
- KPQGOCBYEBQLPS-UHFFFAOYSA-N 2-[2-fluoro-4-[[5-fluoro-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]phenoxy]acetamide Chemical compound C1=C(F)C(OCC(=O)N)=CC=C1NC1=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=C1F KPQGOCBYEBQLPS-UHFFFAOYSA-N 0.000 claims description 2
- KFLOWPTVEJUDRF-UHFFFAOYSA-N 2-[2-fluoro-4-[[5-methyl-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]phenoxy]-n,n-dimethylacetamide Chemical compound C1=C(F)C(OCC(=O)N(C)C)=CC=C1NC1=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=C1C KFLOWPTVEJUDRF-UHFFFAOYSA-N 0.000 claims description 2
- ONUISJRMJLHATK-UHFFFAOYSA-N 2-[2-fluoro-4-[[5-methyl-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]phenoxy]-n-methylacetamide Chemical compound C1=C(F)C(OCC(=O)NC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=C1C ONUISJRMJLHATK-UHFFFAOYSA-N 0.000 claims description 2
- UUHTZLXQDSELLJ-UHFFFAOYSA-N 2-[4-[[5-fluoro-2-(3-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]ethylurea Chemical compound C1=CC(CCNC(=O)N)=CC=C1NC1=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=C1F UUHTZLXQDSELLJ-UHFFFAOYSA-N 0.000 claims description 2
- WGIQBECETWEDKO-UHFFFAOYSA-N 2-[4-[[5-fluoro-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]-2-methoxyphenoxy]acetamide Chemical compound C1=C(OCC(N)=O)C(OC)=CC(NC=2C(=CN=C(NC=3C=CC(=CC=3)S(N)(=O)=O)N=2)F)=C1 WGIQBECETWEDKO-UHFFFAOYSA-N 0.000 claims description 2
- GSQHMQAOWSMYEH-UHFFFAOYSA-N 2-[4-[[5-fluoro-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]phenoxy]-n,n-dimethylacetamide Chemical compound C1=CC(OCC(=O)N(C)C)=CC=C1NC1=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=C1F GSQHMQAOWSMYEH-UHFFFAOYSA-N 0.000 claims description 2
- KYOYQBSGQSWRTH-UHFFFAOYSA-N 2-[4-[[5-fluoro-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]phenoxy]-n-methylacetamide Chemical compound C1=CC(OCC(=O)NC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)S(N)(=O)=O)=NC=C1F KYOYQBSGQSWRTH-UHFFFAOYSA-N 0.000 claims description 2
- BCGIZVPEUXXCNQ-UHFFFAOYSA-N 2-[4-[[5-fluoro-2-[4-(4-methylpiperazin-1-yl)sulfonylanilino]pyrimidin-4-yl]amino]-2,6-dimethylphenoxy]acetonitrile Chemical compound C1CN(C)CCN1S(=O)(=O)C(C=C1)=CC=C1NC1=NC=C(F)C(NC=2C=C(C)C(OCC#N)=C(C)C=2)=N1 BCGIZVPEUXXCNQ-UHFFFAOYSA-N 0.000 claims description 2
- AHHVINVBXOLAIM-UHFFFAOYSA-N 2-[4-[[5-methyl-2-(4-sulfamoylanilino)pyrimidin-4-yl]amino]phenoxy]acetamide Chemical compound N1=C(NC=2C=CC(OCC(N)=O)=CC=2)C(C)=CN=C1NC1=CC=C(S(N)(=O)=O)C=C1 AHHVINVBXOLAIM-UHFFFAOYSA-N 0.000 claims description 2
- GPJXQHZORKKWAL-UHFFFAOYSA-N 2-chloro-5-[[2-(4-chloro-3-sulfamoylanilino)-5-fluoropyrimidin-4-yl]amino]benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(NC=2N=C(NC=3C=C(C(Cl)=CC=3)S(N)(=O)=O)C(F)=CN=2)=C1 GPJXQHZORKKWAL-UHFFFAOYSA-N 0.000 claims description 2
- CCEBZTVGDUQUEM-UHFFFAOYSA-N 2-fluoro-5-[[5-fluoro-4-(4-hydroxyanilino)pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=C(F)C(S(=O)(=O)N)=CC(NC=2N=C(NC=3C=CC(O)=CC=3)C(F)=CN=2)=C1 CCEBZTVGDUQUEM-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
- PDMZSTUKICAEPP-UHFFFAOYSA-N 2-methyl-5-[[5-methyl-4-[(3-oxo-4h-1,4-benzoxazin-6-yl)amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=C(S(N)(=O)=O)C(C)=CC=C1NC1=NC=C(C)C(NC=2C=C3NC(=O)COC3=CC=2)=N1 PDMZSTUKICAEPP-UHFFFAOYSA-N 0.000 claims description 2
- CHLCYPMVUQXEOV-UHFFFAOYSA-N 2-methyl-5-[[5-methyl-4-[(4-methyl-3-oxo-1,4-benzothiazin-6-yl)amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=C2N(C)C(=O)CSC2=CC=C1NC(C(=CN=1)C)=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 CHLCYPMVUQXEOV-UHFFFAOYSA-N 0.000 claims description 2
- JAUGLUXFPUOTDA-UHFFFAOYSA-N 3-[[4-(3,4-dichloroanilino)-5-fluoropyrimidin-2-yl]amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=C(Cl)C(Cl)=CC=3)C(F)=CN=2)=C1 JAUGLUXFPUOTDA-UHFFFAOYSA-N 0.000 claims description 2
- LUKLMAGXUUPWTE-UHFFFAOYSA-N 3-[[4-(3-cyano-4-fluoroanilino)-5-fluoropyrimidin-2-yl]amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=C(C(F)=CC=3)C#N)C(F)=CN=2)=C1 LUKLMAGXUUPWTE-UHFFFAOYSA-N 0.000 claims description 2
- OVIBKPIIOIPWMU-UHFFFAOYSA-N 3-[[4-(3-cyano-4-methylanilino)-5-fluoropyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=C(C#N)C(C)=CC=C1NC1=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=C1F OVIBKPIIOIPWMU-UHFFFAOYSA-N 0.000 claims description 2
- QKZOXRIARDHFGL-UHFFFAOYSA-N 3-[[4-[(6-amino-5-methoxypyridin-2-yl)amino]-5-fluoropyrimidin-2-yl]amino]benzenesulfonamide Chemical compound N1=C(N)C(OC)=CC=C1NC1=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=C1F QKZOXRIARDHFGL-UHFFFAOYSA-N 0.000 claims description 2
- BQZHWVKZUFKPGZ-UHFFFAOYSA-N 3-[[4-[[3-(cyanomethyl)-1h-indol-6-yl]amino]-5-fluoropyrimidin-2-yl]amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=C4NC=C(CC#N)C4=CC=3)C(F)=CN=2)=C1 BQZHWVKZUFKPGZ-UHFFFAOYSA-N 0.000 claims description 2
- LPLWDFGPLKXXQZ-UHFFFAOYSA-N 3-[[5-fluoro-2-(3-sulfamoylanilino)pyrimidin-4-yl]amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=C(C=CC=3)S(N)(=O)=O)C(F)=CN=2)=C1 LPLWDFGPLKXXQZ-UHFFFAOYSA-N 0.000 claims description 2
- SCUGNLRJAYZZTA-UHFFFAOYSA-N 3-[[5-fluoro-4-(4-hydroxyanilino)pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=CC(O)=CC=3)C(F)=CN=2)=C1 SCUGNLRJAYZZTA-UHFFFAOYSA-N 0.000 claims description 2
- BXWQTYGKABNEPF-UHFFFAOYSA-N 3-[[5-fluoro-4-[(2,2,4-trimethyl-1,1,3-trioxo-1$l^{6},4-benzothiazin-6-yl)amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=C2N(C)C(=O)C(C)(C)S(=O)(=O)C2=CC=C1NC(C(=CN=1)F)=NC=1NC1=CC=CC(S(N)(=O)=O)=C1 BXWQTYGKABNEPF-UHFFFAOYSA-N 0.000 claims description 2
- SIJFUGGZPUMGFX-UHFFFAOYSA-N 3-[[5-fluoro-4-[(4-methyl-3-oxo-1,4-benzoxazin-6-yl)amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=C2N(C)C(=O)COC2=CC=C1NC(C(=CN=1)F)=NC=1NC1=CC=CC(S(N)(=O)=O)=C1 SIJFUGGZPUMGFX-UHFFFAOYSA-N 0.000 claims description 2
- VOABTIJNANEKFV-UHFFFAOYSA-N 3-[[5-fluoro-4-[(6-methoxypyridin-3-yl)amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=NC(OC)=CC=C1NC1=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=C1F VOABTIJNANEKFV-UHFFFAOYSA-N 0.000 claims description 2
- CLEWCFKCHOACJM-UHFFFAOYSA-N 3-[[5-fluoro-4-[4-(3-fluoropropyl)anilino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=CC(CCCF)=CC=3)C(F)=CN=2)=C1 CLEWCFKCHOACJM-UHFFFAOYSA-N 0.000 claims description 2
- HNHTVALXKVVWFC-UHFFFAOYSA-N 3-[[5-fluoro-4-[4-(3-hydroxypropyl)anilino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=CC(CCCO)=CC=3)C(F)=CN=2)=C1 HNHTVALXKVVWFC-UHFFFAOYSA-N 0.000 claims description 2
- YJWZFFOTZXKRLR-UHFFFAOYSA-N 3-[[5-fluoro-4-[4-(4-fluorobutyl)anilino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=CC(CCCCF)=CC=3)C(F)=CN=2)=C1 YJWZFFOTZXKRLR-UHFFFAOYSA-N 0.000 claims description 2
- VEFSWHJJLKVDFZ-UHFFFAOYSA-N 3-[[5-fluoro-4-[4-(4-hydroxybutyl)anilino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=CC(CCCCO)=CC=3)C(F)=CN=2)=C1 VEFSWHJJLKVDFZ-UHFFFAOYSA-N 0.000 claims description 2
- YZZHIAZOELLZRX-UHFFFAOYSA-N 3-[[5-fluoro-4-[4-(trifluoromethyl)anilino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=CC(=CC=3)C(F)(F)F)C(F)=CN=2)=C1 YZZHIAZOELLZRX-UHFFFAOYSA-N 0.000 claims description 2
- GPGUSCHJPBLYHX-UHFFFAOYSA-N 3-[[5-methyl-4-[(3-oxo-4h-1,4-benzoxazin-6-yl)amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound N1=C(NC=2C=C3NC(=O)COC3=CC=2)C(C)=CN=C1NC1=CC=CC(S(N)(=O)=O)=C1 GPGUSCHJPBLYHX-UHFFFAOYSA-N 0.000 claims description 2
- QOJCOJPJLBPFID-UHFFFAOYSA-N 3-[[5-methyl-4-[(4-methyl-3-oxo-1,4-benzothiazin-6-yl)amino]pyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=C2N(C)C(=O)CSC2=CC=C1NC(C(=CN=1)C)=NC=1NC1=CC=CC(S(N)(=O)=O)=C1 QOJCOJPJLBPFID-UHFFFAOYSA-N 0.000 claims description 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims description 2
- ZXAKYPRKBSFYPF-UHFFFAOYSA-N 4-[[4-(3,4-dichloroanilino)-5-fluoropyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC1=NC=C(F)C(NC=2C=C(Cl)C(Cl)=CC=2)=N1 ZXAKYPRKBSFYPF-UHFFFAOYSA-N 0.000 claims description 2
- HESCAKDVRKTKAC-UHFFFAOYSA-N 4-[[4-(3-chloro-4-methoxyanilino)-5-fluoropyrimidin-2-yl]amino]pyridine-3-sulfonamide Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC(NC=2C(=CN=CC=2)S(N)(=O)=O)=NC=C1F HESCAKDVRKTKAC-UHFFFAOYSA-N 0.000 claims description 2
- YMHXTJMKWPCCKE-UHFFFAOYSA-N 4-[[4-[3-(cyanomethoxy)-4,5-dimethoxyanilino]-5-fluoropyrimidin-2-yl]amino]benzenesulfonamide Chemical compound N#CCOC1=C(OC)C(OC)=CC(NC=2C(=CN=C(NC=3C=CC(=CC=3)S(N)(=O)=O)N=2)F)=C1 YMHXTJMKWPCCKE-UHFFFAOYSA-N 0.000 claims description 2
- OGQZIXOECJFOTF-UHFFFAOYSA-N 4-[[4-[3-chloro-4-(cyanomethoxy)anilino]-5-fluoropyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC1=NC=C(F)C(NC=2C=C(Cl)C(OCC#N)=CC=2)=N1 OGQZIXOECJFOTF-UHFFFAOYSA-N 0.000 claims description 2
- IQIICWJWPCLSOT-UHFFFAOYSA-N 4-[[4-[4-(cyanomethoxy)-3-[1-(cyanomethyl)pyrazol-3-yl]anilino]-5-fluoropyrimidin-2-yl]amino]benzenesulfonamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1NC1=NC=C(F)C(NC=2C=C(C(OCC#N)=CC=2)C2=NN(CC#N)C=C2)=N1 IQIICWJWPCLSOT-UHFFFAOYSA-N 0.000 claims description 2
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- PKHZOBQYJQPMCU-UHFFFAOYSA-N 5-[[5-fluoro-4-[4-(2-morpholin-4-yl-2-oxoethoxy)anilino]pyrimidin-2-yl]amino]-2-methylbenzenesulfonamide Chemical compound C1=C(S(N)(=O)=O)C(C)=CC=C1NC1=NC=C(F)C(NC=2C=CC(OCC(=O)N3CCOCC3)=CC=2)=N1 PKHZOBQYJQPMCU-UHFFFAOYSA-N 0.000 description 1
- JUNVIFBFLDBXBX-UHFFFAOYSA-N 5-[[5-fluoro-4-[4-(2h-triazol-4-ylmethyl)anilino]pyrimidin-2-yl]amino]-2-methylbenzenesulfonamide Chemical compound C1=C(S(N)(=O)=O)C(C)=CC=C1NC1=NC=C(F)C(NC=2C=CC(CC=3N=NNC=3)=CC=2)=N1 JUNVIFBFLDBXBX-UHFFFAOYSA-N 0.000 description 1
- HMAOIDRWGLRWQY-UHFFFAOYSA-N 5-[[5-fluoro-4-[4-(2h-triazol-4-ylmethyl)anilino]pyrimidin-2-yl]amino]-n,2-dimethylbenzenesulfonamide Chemical compound C1=C(C)C(S(=O)(=O)NC)=CC(NC=2N=C(NC=3C=CC(CC=4N=NNC=4)=CC=3)C(F)=CN=2)=C1 HMAOIDRWGLRWQY-UHFFFAOYSA-N 0.000 description 1
- YWKPMSDXISFQLQ-UHFFFAOYSA-N 5-[[5-fluoro-4-[4-(4-methylpiperazine-1-carbonyl)anilino]pyrimidin-2-yl]amino]-2-methylbenzenesulfonamide Chemical compound C1CN(C)CCN1C(=O)C(C=C1)=CC=C1NC1=NC(NC=2C=C(C(C)=CC=2)S(N)(=O)=O)=NC=C1F YWKPMSDXISFQLQ-UHFFFAOYSA-N 0.000 description 1
- AIWGOBVGTYYXIX-UHFFFAOYSA-N 5-[[5-fluoro-4-[4-(pyridin-3-ylmethoxy)anilino]pyrimidin-2-yl]amino]-2-methylbenzenesulfonamide Chemical compound C1=C(S(N)(=O)=O)C(C)=CC=C1NC1=NC=C(F)C(NC=2C=CC(OCC=3C=NC=CC=3)=CC=2)=N1 AIWGOBVGTYYXIX-UHFFFAOYSA-N 0.000 description 1
- UMXSGNRLHBZPLR-UHFFFAOYSA-N 5-[[5-fluoro-4-[4-(pyridin-4-ylmethyl)anilino]pyrimidin-2-yl]amino]-2-methoxybenzenesulfonamide Chemical compound C1=C(S(N)(=O)=O)C(OC)=CC=C1NC1=NC=C(F)C(NC=2C=CC(CC=3C=CN=CC=3)=CC=2)=N1 UMXSGNRLHBZPLR-UHFFFAOYSA-N 0.000 description 1
- CORJMVZDIVOFRX-UHFFFAOYSA-N 5-[[5-fluoro-4-[4-(pyridin-4-ylmethyl)anilino]pyrimidin-2-yl]amino]-2-methylbenzenesulfonamide Chemical compound C1=C(S(N)(=O)=O)C(C)=CC=C1NC1=NC=C(F)C(NC=2C=CC(CC=3C=CN=CC=3)=CC=2)=N1 CORJMVZDIVOFRX-UHFFFAOYSA-N 0.000 description 1
- CEIURZUGGKXDJP-UHFFFAOYSA-N 5-[[5-fluoro-4-[4-(thiomorpholine-4-carbonyl)anilino]pyrimidin-2-yl]amino]-2-methylbenzenesulfonamide Chemical compound C1=C(S(N)(=O)=O)C(C)=CC=C1NC1=NC=C(F)C(NC=2C=CC(=CC=2)C(=O)N2CCSCC2)=N1 CEIURZUGGKXDJP-UHFFFAOYSA-N 0.000 description 1
- NSESYLRNKJCNEV-UHFFFAOYSA-N 5-[[5-fluoro-4-[4-(trifluoromethyl)anilino]pyrimidin-2-yl]amino]-2-methoxy-3-methylbenzenesulfonamide Chemical compound C1=C(S(N)(=O)=O)C(OC)=C(C)C=C1NC1=NC=C(F)C(NC=2C=CC(=CC=2)C(F)(F)F)=N1 NSESYLRNKJCNEV-UHFFFAOYSA-N 0.000 description 1
- GMCAJKZZXRJCCN-UHFFFAOYSA-N 5-[[5-fluoro-4-[4-[(2-methylimidazol-2-yl)methyl]anilino]pyrimidin-2-yl]amino]-n,2-dimethylbenzenesulfonamide Chemical compound C1=C(C)C(S(=O)(=O)NC)=CC(NC=2N=C(NC=3C=CC(CC4(C)N=CC=N4)=CC=3)C(F)=CN=2)=C1 GMCAJKZZXRJCCN-UHFFFAOYSA-N 0.000 description 1
- ZLFAXFYHFMWHAP-UHFFFAOYSA-N 5-[[5-fluoro-4-[4-[(5-methyl-1,3,4-oxadiazol-2-yl)methoxy]anilino]pyrimidin-2-yl]amino]-2-methylbenzenesulfonamide Chemical compound O1C(C)=NN=C1COC(C=C1)=CC=C1NC1=NC(NC=2C=C(C(C)=CC=2)S(N)(=O)=O)=NC=C1F ZLFAXFYHFMWHAP-UHFFFAOYSA-N 0.000 description 1
- FFFXDHNOQLTRRP-UHFFFAOYSA-N 5-[[5-fluoro-4-[4-methyl-3-(2-morpholin-4-ylethoxy)anilino]pyrimidin-2-yl]amino]-2-methylbenzenesulfonamide Chemical compound C1=C(OCCN2CCOCC2)C(C)=CC=C1NC(C(=CN=1)F)=NC=1NC1=CC=C(C)C(S(N)(=O)=O)=C1 FFFXDHNOQLTRRP-UHFFFAOYSA-N 0.000 description 1
- UWBYXLWXDRBEMZ-UHFFFAOYSA-N 5-fluoro-4-n-[4-(2-morpholin-4-ylethoxy)phenyl]-2-n-(3-morpholin-4-ylsulfonylphenyl)pyrimidine-2,4-diamine Chemical compound N1=C(NC=2C=CC(OCCN3CCOCC3)=CC=2)C(F)=CN=C1NC(C=1)=CC=CC=1S(=O)(=O)N1CCOCC1 UWBYXLWXDRBEMZ-UHFFFAOYSA-N 0.000 description 1
- JKTBBXJVGSCSPX-UHFFFAOYSA-N 6-[[5-fluoro-2-(3-piperidin-1-ylsulfonylanilino)pyrimidin-4-yl]amino]-4-methyl-1,4-benzothiazin-3-one Chemical compound C1=C2N(C)C(=O)CSC2=CC=C1NC(C(=CN=1)F)=NC=1NC(C=1)=CC=CC=1S(=O)(=O)N1CCCCC1 JKTBBXJVGSCSPX-UHFFFAOYSA-N 0.000 description 1
- AIKDWEXMJCXGFJ-UHFFFAOYSA-N C1=C(Cl)C(OC)=CC=C1NC1=NC(N)(C=2C=C(C(C)=CC=2)S(N)(=O)=O)NC=C1Br Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC(N)(C=2C=C(C(C)=CC=2)S(N)(=O)=O)NC=C1Br AIKDWEXMJCXGFJ-UHFFFAOYSA-N 0.000 description 1
- 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 102000000551 Syk Kinase Human genes 0.000 description 1
- 108010016672 Syk Kinase Proteins 0.000 description 1
- 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 description 1
- VGYWXNDXVIRUPF-UHFFFAOYSA-N [4-[[5-fluoro-2-(3-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]methylurea Chemical compound C1=CC(CNC(=O)N)=CC=C1NC1=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=C1F VGYWXNDXVIRUPF-UHFFFAOYSA-N 0.000 description 1
- LCZLFHFWNDGSDK-UHFFFAOYSA-N [4-[[5-fluoro-2-(4-methyl-3-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]methylurea Chemical compound C1=C(S(N)(=O)=O)C(C)=CC=C1NC1=NC=C(F)C(NC=2C=CC(CNC(N)=O)=CC=2)=N1 LCZLFHFWNDGSDK-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 230000001363 autoimmune Effects 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- QHBREUPPKZDCEW-UHFFFAOYSA-N methyl 2-[4-[[5-fluoro-2-[4-methyl-3-(propanoylsulfamoyl)anilino]pyrimidin-4-yl]amino]phenoxy]acetate Chemical compound C1=C(C)C(S(=O)(=O)NC(=O)CC)=CC(NC=2N=C(NC=3C=CC(OCC(=O)OC)=CC=3)C(F)=CN=2)=C1 QHBREUPPKZDCEW-UHFFFAOYSA-N 0.000 description 1
- VAWRULOLYNMUKJ-UHFFFAOYSA-N methyl 5-[[5-fluoro-2-(3-sulfamoylanilino)pyrimidin-4-yl]amino]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1NC1=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=C1F VAWRULOLYNMUKJ-UHFFFAOYSA-N 0.000 description 1
- ARNQNZSUMHALMJ-UHFFFAOYSA-N methyl 5-[[5-fluoro-2-(4-fluoro-3-sulfamoylanilino)pyrimidin-4-yl]amino]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1NC1=NC(NC=2C=C(C(F)=CC=2)S(N)(=O)=O)=NC=C1F ARNQNZSUMHALMJ-UHFFFAOYSA-N 0.000 description 1
- BRIYDDLCTBTABF-UHFFFAOYSA-N methyl 5-[[5-fluoro-2-(4-methyl-3-sulfamoylanilino)pyrimidin-4-yl]amino]thiophene-2-carboxylate Chemical compound S1C(C(=O)OC)=CC=C1NC1=NC(NC=2C=C(C(C)=CC=2)S(N)(=O)=O)=NC=C1F BRIYDDLCTBTABF-UHFFFAOYSA-N 0.000 description 1
- VFRPECLJKCUOSI-UHFFFAOYSA-N n-[2-chloro-5-[[4-(3-chloro-4-methoxyanilino)-5-fluoropyrimidin-2-yl]amino]phenyl]sulfonylacetamide Chemical compound C1=C(Cl)C(OC)=CC=C1NC1=NC(NC=2C=C(C(Cl)=CC=2)S(=O)(=O)NC(C)=O)=NC=C1F VFRPECLJKCUOSI-UHFFFAOYSA-N 0.000 description 1
- PNNWNUOANAFYQR-UHFFFAOYSA-N n-[[4-[[5-fluoro-2-(3-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]methyl]prop-2-enamide Chemical compound NS(=O)(=O)C1=CC=CC(NC=2N=C(NC=3C=CC(CNC(=O)C=C)=CC=3)C(F)=CN=2)=C1 PNNWNUOANAFYQR-UHFFFAOYSA-N 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- XXULMLOENPXCIO-UHFFFAOYSA-N s-[2-[4-[[5-fluoro-2-(3-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]-2-oxoethyl] ethanethioate Chemical compound C1=CC(C(=O)CSC(=O)C)=CC=C1NC1=NC(NC=2C=C(C=CC=2)S(N)(=O)=O)=NC=C1F XXULMLOENPXCIO-UHFFFAOYSA-N 0.000 description 1
- SMIIULRICOQUSH-UHFFFAOYSA-N s-[2-[4-[[5-fluoro-2-(4-methyl-3-sulfamoylanilino)pyrimidin-4-yl]amino]phenyl]-2-oxoethyl] ethanethioate Chemical compound C1=CC(C(=O)CSC(=O)C)=CC=C1NC1=NC(NC=2C=C(C(C)=CC=2)S(N)(=O)=O)=NC=C1F SMIIULRICOQUSH-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- 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
- C07D413/12—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 linked by a chain containing hetero atoms as chain links
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- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
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- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/436—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having oxygen as a ring hetero atom, e.g. rapamycin
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim not condensed and containing further heterocyclic rings
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- A61K31/5375—1,4-Oxazines, e.g. morpholine
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- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/12—Cyclic peptides, e.g. bacitracins; Polymyxins; Gramicidins S, C; Tyrocidins A, B or C
- A61K38/13—Cyclosporins
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- A61K39/395—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum
- A61K39/39533—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum against materials from animals
- A61K39/3955—Antibodies; Immunoglobulins; Immune serum, e.g. antilymphocytic serum against materials from animals against proteinaceous materials, e.g. enzymes, hormones, lymphokines
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- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
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- C07D285/20—1,2,4-Thiadiazines; Hydrogenated 1,2,4-thiadiazines condensed with carbocyclic rings or ring systems
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| US77663606P | 2006-02-24 | 2006-02-24 | |
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| PCT/US2006/022590 WO2006133426A2 (en) | 2005-06-08 | 2006-06-08 | Compositions and methods for inhibition of the jak pathway |
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