JP2009534420A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2009534420A5 JP2009534420A5 JP2009506793A JP2009506793A JP2009534420A5 JP 2009534420 A5 JP2009534420 A5 JP 2009534420A5 JP 2009506793 A JP2009506793 A JP 2009506793A JP 2009506793 A JP2009506793 A JP 2009506793A JP 2009534420 A5 JP2009534420 A5 JP 2009534420A5
- Authority
- JP
- Japan
- Prior art keywords
- chloro
- urea
- hydroxyphenyl
- phenyl
- diazabicyclo
- 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.)
- Pending
Links
- -1 phenyloxy Chemical group 0.000 claims 33
- 150000001875 compounds Chemical class 0.000 claims 26
- 125000000217 alkyl group Chemical group 0.000 claims 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical group 0.000 claims 8
- 102000019034 Chemokines Human genes 0.000 claims 7
- 108010012236 Chemokines Proteins 0.000 claims 7
- 201000010099 disease Diseases 0.000 claims 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 7
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 6
- 241000124008 Mammalia Species 0.000 claims 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 6
- 239000004202 carbamide Substances 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 5
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 230000001404 mediated effect Effects 0.000 claims 5
- 238000000034 method Methods 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 5
- GZBLFQYBTDMOIN-MQVJKMGUSA-N 1-[3-[[(1s,5r)-3-(butylamino)-8-azabicyclo[3.2.1]octan-8-yl]sulfonyl]-4-chloro-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound N1([C@]2([H])CC[C@]1(CC(C2)NCCCC)[H])S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1Cl GZBLFQYBTDMOIN-MQVJKMGUSA-N 0.000 claims 4
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims 4
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims 4
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims 4
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims 4
- 208000006673 asthma Diseases 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- MJMBYVFAKNILJO-OKILXGFUSA-N 1-[4-chloro-2-hydroxy-3-[[(1r,5s)-3-hydroxyimino-8-azabicyclo[3.2.1]octan-8-yl]sulfonyl]phenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound N1([C@]2([H])CC[C@]1(CC(C2)=NO)[H])S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1C MJMBYVFAKNILJO-OKILXGFUSA-N 0.000 claims 3
- ZBDSJFYZOPFXIP-GOOCMWNKSA-N 1-[4-chloro-2-hydroxy-3-[[(1s,5r)-3-(methylamino)-8-azabicyclo[3.2.1]octan-8-yl]sulfonyl]phenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound N1([C@]2([H])CC[C@]1(CC(C2)NC)[H])S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1C ZBDSJFYZOPFXIP-GOOCMWNKSA-N 0.000 claims 3
- RNNBGAHBGNJAGE-UHFFFAOYSA-N 1-[4-chloro-3-(3,8-diazabicyclo[3.2.1]octan-3-ylsulfonyl)-2-hydroxyphenyl]-3-(2-phenoxyphenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CC3CCC(N3)C2)C(O)=C1NC(=O)NC1=CC=CC=C1OC1=CC=CC=C1 RNNBGAHBGNJAGE-UHFFFAOYSA-N 0.000 claims 3
- HONMASBTBAPAJJ-UHFFFAOYSA-N 1-[4-chloro-3-(3,8-diazabicyclo[3.2.1]octan-3-ylsulfonyl)-2-hydroxyphenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound CC1=C(F)C=CC=C1NC(=O)NC1=CC=C(Cl)C(S(=O)(=O)N2CC3CCC(N3)C2)=C1O HONMASBTBAPAJJ-UHFFFAOYSA-N 0.000 claims 3
- AUIYZBPIYFZKJY-GOOCMWNKSA-N 1-[4-chloro-3-[[(1r,5s)-3-(cyclopropylamino)-8-azabicyclo[3.2.1]octan-8-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C([C@]1(CC[C@@](C2)(N1S(=O)(=O)C=1C(=C(NC(=O)NC=3C(=C(F)C=CC=3)Cl)C=CC=1Cl)O)[H])[H])C2NC1CC1 AUIYZBPIYFZKJY-GOOCMWNKSA-N 0.000 claims 3
- UKEODWQYKLFNKV-AGUYFDCRSA-N 1-[4-chloro-3-[[(1r,5s)-3-(ethylamino)-8-azabicyclo[3.2.1]octan-8-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound N1([C@]2([H])CC[C@]1(CC(C2)NCC)[H])S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1Cl UKEODWQYKLFNKV-AGUYFDCRSA-N 0.000 claims 3
- WUMHAFGYRJQVAA-MQVJKMGUSA-N 1-[4-chloro-3-[[(1r,5s)-3-(ethylamino)-8-azabicyclo[3.2.1]octan-8-yl]sulfonyl]-2-hydroxyphenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound N1([C@]2([H])CC[C@]1(CC(C2)NCC)[H])S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1C WUMHAFGYRJQVAA-MQVJKMGUSA-N 0.000 claims 3
- XJPKPJLOCXRDSH-KBPBESRZSA-N 1-[4-chloro-3-[[(1s,4s)-5-(cyclopropylmethyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C([C@]1(N(C[C@@]2(C1)[H])S(=O)(=O)C=1C(=CC=C(NC(=O)NC=3C(=C(F)C=CC=3)Cl)C=1O)Cl)[H])N2CC1CC1 XJPKPJLOCXRDSH-KBPBESRZSA-N 0.000 claims 3
- XGGAKJCYUCGHMZ-PHIMTYICSA-N 1-[4-chloro-3-[[(1s,5r)-3,8-diazabicyclo[3.2.1]octan-8-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound N1([C@]2([H])CC[C@]1(CNC2)[H])S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1Cl XGGAKJCYUCGHMZ-PHIMTYICSA-N 0.000 claims 3
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 3
- 206010040070 Septic Shock Diseases 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 3
- GQHISURWNNDZTN-RYUDHWBXSA-N 1-(2-chloro-3-fluorophenyl)-3-[4-chloro-2-hydroxy-3-[[(1s,4s)-5-(2-hydroxyethyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]phenyl]urea Chemical compound C([C@]1(N(C[C@]2([H])C1)CCO)[H])N2S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CC(F)=C1Cl GQHISURWNNDZTN-RYUDHWBXSA-N 0.000 claims 2
- ZGFRYCRDXCTXBA-QWRGUYRKSA-N 1-(2-chloro-3-fluorophenyl)-3-[4-chloro-2-hydroxy-3-[[(1s,4s)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]phenyl]urea Chemical compound C([C@]1(N(C[C@]2([H])C1)C)[H])N2S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1Cl ZGFRYCRDXCTXBA-QWRGUYRKSA-N 0.000 claims 2
- DAZVVDHMHGRJEE-OALUTQOASA-N 1-[4-chloro-2-hydroxy-3-[[(1s,4s)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]phenyl]-3-(2-phenylmethoxyphenyl)urea Chemical compound C([C@]1(N(C[C@]2([H])C1)C)[H])N2S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CC=C1OCC1=CC=CC=C1 DAZVVDHMHGRJEE-OALUTQOASA-N 0.000 claims 2
- HSBKLRQSRFANNZ-UHFFFAOYSA-N 1-[4-chloro-3-(1,8-diazaspiro[4.5]decan-8-ylsulfonyl)-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CCC3(NCCC3)CC2)C(O)=C1NC(=O)NC1=CC=CC(F)=C1Cl HSBKLRQSRFANNZ-UHFFFAOYSA-N 0.000 claims 2
- DWMIADSRLTYJBG-UHFFFAOYSA-N 1-[4-chloro-3-(1,8-diazaspiro[4.5]decan-8-ylsulfonyl)-2-hydroxyphenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound CC1=C(F)C=CC=C1NC(=O)NC1=CC=C(Cl)C(S(=O)(=O)N2CCC3(NCCC3)CC2)=C1O DWMIADSRLTYJBG-UHFFFAOYSA-N 0.000 claims 2
- ACQFHYAQGLSNAC-UHFFFAOYSA-N 1-[4-chloro-3-(6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-ylsulfonyl)-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CC3=NC=CN3CC2)C(O)=C1NC(=O)NC1=CC=CC(F)=C1Cl ACQFHYAQGLSNAC-UHFFFAOYSA-N 0.000 claims 2
- DNOKBVYRPWLULP-ZJUUUORDSA-N 1-[4-chloro-3-[[(1s,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C([C@@]1(NC[C@]2([H])C1)[H])N2S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CC(F)=C1Cl DNOKBVYRPWLULP-ZJUUUORDSA-N 0.000 claims 2
- DNOKBVYRPWLULP-UWVGGRQHSA-N 1-[4-chloro-3-[[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CC(F)=C1Cl DNOKBVYRPWLULP-UWVGGRQHSA-N 0.000 claims 2
- UNIWORFJYDXWQB-HOTGVXAUSA-N 1-[4-chloro-3-[[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-phenoxyphenyl)urea Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CC=C1OC1=CC=CC=C1 UNIWORFJYDXWQB-HOTGVXAUSA-N 0.000 claims 2
- QKZATTLECOGXEB-ROUUACIJSA-N 1-[4-chloro-3-[[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-phenylmethoxyphenyl)urea Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CC=C1OCC1=CC=CC=C1 QKZATTLECOGXEB-ROUUACIJSA-N 0.000 claims 2
- NBNZDLOYGFNKSX-PHIMTYICSA-N 1-[4-chloro-3-[[(1s,5r)-3,8-diazabicyclo[3.2.1]octan-3-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C([C@]1(CC[C@@](C2)(N1)[H])[H])N2S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1Cl NBNZDLOYGFNKSX-PHIMTYICSA-N 0.000 claims 2
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical compound NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 claims 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 239000012948 isocyanate Substances 0.000 claims 2
- 150000002513 isocyanates Chemical class 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 claims 1
- GBVWZFOKWBOKSZ-PHIMTYICSA-N 1-(2-chloro-3-fluorophenyl)-3-[4-chloro-2-hydroxy-3-[[(1s,5r)-3-oxo-8-azabicyclo[3.2.1]octan-8-yl]sulfonyl]phenyl]urea Chemical compound N1([C@]2([H])CC[C@]1(CC(=O)C2)[H])S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CC(F)=C1Cl GBVWZFOKWBOKSZ-PHIMTYICSA-N 0.000 claims 1
- CHWTWYIXLKQNQB-UHFFFAOYSA-N 1-[3-(1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridin-5-ylsulfonyl)-4-chloro-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CC3CCNC3CC2)C(O)=C1NC(=O)NC1=CC=CC(F)=C1Cl CHWTWYIXLKQNQB-UHFFFAOYSA-N 0.000 claims 1
- SEGNSEUXIMDNPI-UHFFFAOYSA-N 1-[3-(1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridin-5-ylsulfonyl)-4-chloro-2-hydroxyphenyl]-3-(2-chloropyridin-3-yl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CC3CCNC3CC2)C(O)=C1NC(=O)NC1=CC=CN=C1Cl SEGNSEUXIMDNPI-UHFFFAOYSA-N 0.000 claims 1
- MSWCEQJQBLVFIL-UHFFFAOYSA-N 1-[3-(1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,2-c]pyridin-5-ylsulfonyl)-4-chloro-2-hydroxyphenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound CC1=C(F)C=CC=C1NC(=O)NC1=CC=C(Cl)C(S(=O)(=O)N2CC3CCNC3CC2)=C1O MSWCEQJQBLVFIL-UHFFFAOYSA-N 0.000 claims 1
- QLMRDUBUVLKBGI-UHFFFAOYSA-N 1-[3-[(3-benzyl-3,8-diazabicyclo[3.2.1]octan-8-yl)sulfonyl]-4-chloro-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2C3CCC2CN(CC=2C=CC=CC=2)C3)C(O)=C1NC(=O)NC1=CC=CC(F)=C1Cl QLMRDUBUVLKBGI-UHFFFAOYSA-N 0.000 claims 1
- MXUATWBPBVOFSG-WOJBJXKFSA-N 1-[3-[[(1r,5r)-8-benzyl-3,8-diazabicyclo[3.2.1]octan-3-yl]sulfonyl]-4-chloro-2-hydroxyphenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound C([C@]1(CC[C@](C2)(N1CC=1C=CC=CC=1)[H])[H])N2S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1C MXUATWBPBVOFSG-WOJBJXKFSA-N 0.000 claims 1
- VNXUBUYGDOEUNX-AYHJJNSGSA-N 1-[3-[[(1r,5s)-3-(butylamino)-8-azabicyclo[3.2.1]octan-8-yl]sulfonyl]-4-chloro-2-hydroxyphenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound N1([C@]2([H])CC[C@]1(CC(C2)NCCCC)[H])S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1C VNXUBUYGDOEUNX-AYHJJNSGSA-N 0.000 claims 1
- FSTBHAOLTGRZFJ-PBWFPOADSA-N 1-[3-[[(1r,5s)-8-azabicyclo[3.2.1]octan-3-yl]sulfamoyl]-4-chloro-2-hydroxyphenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound C([C@]1(CC[C@@](C2)(N1)[H])[H])C2NS(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1C FSTBHAOLTGRZFJ-PBWFPOADSA-N 0.000 claims 1
- JCPBTWNWWDTTTI-FOSCPWQOSA-N 1-[3-[[(1s,5r)-8-azabicyclo[3.2.1]octan-3-yl]sulfamoyl]-4-chloro-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C([C@]1(CC[C@@](C2)(N1)[H])[H])C2NS(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1Cl JCPBTWNWWDTTTI-FOSCPWQOSA-N 0.000 claims 1
- UHTDYTDNMSYVNS-MRXNPFEDSA-N 1-[3-[[(3s)-1-azabicyclo[2.2.2]octan-3-yl]sulfamoyl]-4-chloro-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N[C@H]2C3CCN(CC3)C2)C(O)=C1NC(=O)NC1=CC=CC(F)=C1Cl UHTDYTDNMSYVNS-MRXNPFEDSA-N 0.000 claims 1
- HTNYBKNNYOEOFO-PHIMTYICSA-N 1-[4-chloro-2-hydroxy-3-[[(1r,5s)-3-oxo-8-azabicyclo[3.2.1]octan-8-yl]sulfonyl]phenyl]-3-(2,2-difluoro-1,3-benzodioxol-4-yl)urea Chemical compound N1([C@]2([H])CC[C@]1(CC(=O)C2)[H])S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC2=C1OC(F)(F)O2 HTNYBKNNYOEOFO-PHIMTYICSA-N 0.000 claims 1
- LWQJHWZPPFFHCA-ALOPSCKCSA-N 1-[4-chloro-2-hydroxy-3-[[(1s,5r)-3-(propylamino)-8-azabicyclo[3.2.1]octan-8-yl]sulfonyl]phenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound N1([C@]2([H])CC[C@]1(CC(C2)NCCC)[H])S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1C LWQJHWZPPFFHCA-ALOPSCKCSA-N 0.000 claims 1
- CBYWOYRIOIDQCQ-PHIMTYICSA-N 1-[4-chloro-2-hydroxy-3-[[(1s,5r)-3-oxo-8-azabicyclo[3.2.1]octan-8-yl]sulfonyl]phenyl]-3-(2-chloropyridin-3-yl)urea Chemical compound N1([C@]2([H])CC[C@]1(CC(=O)C2)[H])S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CN=C1Cl CBYWOYRIOIDQCQ-PHIMTYICSA-N 0.000 claims 1
- ASDFMPKGRQQQOW-BETUJISGSA-N 1-[4-chloro-2-hydroxy-3-[[(1s,5r)-3-oxo-8-azabicyclo[3.2.1]octan-8-yl]sulfonyl]phenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound N1([C@]2([H])CC[C@]1(CC(=O)C2)[H])S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1C ASDFMPKGRQQQOW-BETUJISGSA-N 0.000 claims 1
- ZDJFKZQIMPXIHG-UHFFFAOYSA-N 1-[4-chloro-3-(1,8-diazaspiro[4.5]decan-8-ylsulfonyl)-2-hydroxyphenyl]-3-(2-ethylphenyl)urea Chemical compound CCC1=CC=CC=C1NC(=O)NC1=CC=C(Cl)C(S(=O)(=O)N2CCC3(NCCC3)CC2)=C1O ZDJFKZQIMPXIHG-UHFFFAOYSA-N 0.000 claims 1
- RCYAOPOAKRDRPB-UHFFFAOYSA-N 1-[4-chloro-3-(1,8-diazaspiro[4.5]decan-8-ylsulfonyl)-2-hydroxyphenyl]-3-[2-(trifluoromethoxy)phenyl]urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CCC3(NCCC3)CC2)C(O)=C1NC(=O)NC1=CC=CC=C1OC(F)(F)F RCYAOPOAKRDRPB-UHFFFAOYSA-N 0.000 claims 1
- OZVJRQMLLBIHEU-UHFFFAOYSA-N 1-[4-chloro-3-(3,8-diazabicyclo[3.2.1]octan-3-ylsulfonyl)-2-hydroxyphenyl]-3-(2-chloropyridin-3-yl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CC3CCC(N3)C2)C(O)=C1NC(=O)NC1=CC=CN=C1Cl OZVJRQMLLBIHEU-UHFFFAOYSA-N 0.000 claims 1
- ARHDPHGWDPKXBY-UHFFFAOYSA-N 1-[4-chloro-3-(6,8-dihydro-5h-imidazo[1,2-a]pyrazin-7-ylsulfonyl)-2-hydroxyphenyl]-3-(2-ethylphenyl)urea Chemical compound CCC1=CC=CC=C1NC(=O)NC1=CC=C(Cl)C(S(=O)(=O)N2CC3=NC=CN3CC2)=C1O ARHDPHGWDPKXBY-UHFFFAOYSA-N 0.000 claims 1
- CAEYRRAGTFPSHP-NXEZZACHSA-N 1-[4-chloro-3-[[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloropyridin-3-yl)urea Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CN=C1Cl CAEYRRAGTFPSHP-NXEZZACHSA-N 0.000 claims 1
- MDNQCHUMXKZCIP-ZIAGYGMSSA-N 1-[4-chloro-3-[[(1r,4r)-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-ethylphenyl)urea Chemical compound C([C@@]1(NC[C@@]2([H])C1)[H])N2S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CC=C1CC MDNQCHUMXKZCIP-ZIAGYGMSSA-N 0.000 claims 1
- PYNFRFIWPMMKGG-TXEJJXNPSA-N 1-[4-chloro-3-[[(1r,5s)-3,7-diazabicyclo[3.3.1]nonan-3-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloropyridin-3-yl)urea Chemical compound C([C@]1(CNC[C@@](C2)(C1)[H])[H])N2S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CN=C1Cl PYNFRFIWPMMKGG-TXEJJXNPSA-N 0.000 claims 1
- HDNYZFWDYAMMPN-RYUDHWBXSA-N 1-[4-chloro-3-[[(1s,4s)-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]-2-hydroxyphenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound C([C@]1(NC[C@]2([H])C1)[H])N2S(=O)(=O)C(C(=CC=1)Cl)=C(O)C=1NC(=O)NC1=CC=CC(F)=C1C HDNYZFWDYAMMPN-RYUDHWBXSA-N 0.000 claims 1
- OFSSPCTUNWAUNU-VXKWHMMOSA-N 1-[4-chloro-3-[[(1s,4s)-5-(cyclopropylmethyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-phenylmethoxyphenyl)urea Chemical compound C([C@]1(N(C[C@@]2(C1)[H])S(=O)(=O)C=1C(=C(NC(=O)NC=3C(=CC=CC=3)OCC=3C=CC=CC=3)C=CC=1Cl)O)[H])N2CC1CC1 OFSSPCTUNWAUNU-VXKWHMMOSA-N 0.000 claims 1
- UVDILLOVMZZMCF-HOTGVXAUSA-N 1-[4-chloro-3-[[(1s,4s)-5-(cyclopropylmethyl)-2,5-diazabicyclo[2.2.1]heptan-2-yl]sulfonyl]-2-hydroxyphenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound C([C@]1(N(C[C@@]2(C1)[H])S(=O)(=O)C=1C(=CC=C(NC(=O)NC=3C(=C(F)C=CC=3)C)C=1O)Cl)[H])N2CC1CC1 UVDILLOVMZZMCF-HOTGVXAUSA-N 0.000 claims 1
- WNXDIFWWDCPOBV-AYHJJNSGSA-N 1-[4-chloro-3-[[(1s,5r)-3-(cyclopropylmethylamino)-8-azabicyclo[3.2.1]octan-8-yl]sulfonyl]-2-hydroxyphenyl]-3-(3-fluoro-2-methylphenyl)urea Chemical compound C([C@]1(CC[C@@](C2)(N1S(=O)(=O)C=1C(=C(NC(=O)NC=3C(=C(F)C=CC=3)C)C=CC=1Cl)O)[H])[H])C2NCC1CC1 WNXDIFWWDCPOBV-AYHJJNSGSA-N 0.000 claims 1
- APKOVQXQUOWYQH-RYUDHWBXSA-N 1-[4-chloro-3-[[(1s,5s)-3,7-diazabicyclo[3.3.1]nonan-3-yl]sulfonyl]-2-hydroxyphenyl]-3-(2-chloro-3-fluorophenyl)urea Chemical compound C([C@@]1(CNC[C@@](C2)(C1)[H])[H])N2S(=O)(=O)C(C=1O)=C(Cl)C=CC=1NC(=O)NC1=CC=CC(F)=C1Cl APKOVQXQUOWYQH-RYUDHWBXSA-N 0.000 claims 1
- 125000005983 2,5-diazabicyclo[2.2.1]heptan-2-yl group Chemical group 0.000 claims 1
- 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 claims 1
- ZERCTXGMBRAWQP-UHFFFAOYSA-N 8-azabicyclo[3.2.1]octan-3-amine Chemical group C1C(N)CC2CCC1N2 ZERCTXGMBRAWQP-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 241000709661 Enterovirus Species 0.000 claims 1
- 206010018364 Glomerulonephritis Diseases 0.000 claims 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000007536 Thrombosis Diseases 0.000 claims 1
- 206010044248 Toxic shock syndrome Diseases 0.000 claims 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 210000004204 blood vessel Anatomy 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000012467 final product Substances 0.000 claims 1
- 208000007565 gingivitis Diseases 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 210000003958 hematopoietic stem cell Anatomy 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 210000003734 kidney Anatomy 0.000 claims 1
- 201000004792 malaria Diseases 0.000 claims 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 208000013223 septicemia Diseases 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 230000003612 virological effect Effects 0.000 claims 1
- 0 CC(C)(C)c1nc2ccc(*)c(S(*)(=O)=O)c2[o]1 Chemical compound CC(C)(C)c1nc2ccc(*)c(S(*)(=O)=O)c2[o]1 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79383606P | 2006-04-21 | 2006-04-21 | |
| PCT/US2007/067088 WO2007124423A2 (en) | 2006-04-21 | 2007-04-20 | Il-8 receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2009534420A JP2009534420A (ja) | 2009-09-24 |
| JP2009534420A5 true JP2009534420A5 (enExample) | 2010-06-17 |
Family
ID=38625765
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009506793A Pending JP2009534420A (ja) | 2006-04-21 | 2007-04-20 | Ｉｌ−８受容体アンタゴニスト |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8097626B2 (enExample) |
| EP (1) | EP2010180A4 (enExample) |
| JP (1) | JP2009534420A (enExample) |
| CN (1) | CN101495113A (enExample) |
| AU (1) | AU2007240364A1 (enExample) |
| BR (1) | BRPI0710559A2 (enExample) |
| CA (1) | CA2650007A1 (enExample) |
| IL (1) | IL194700A0 (enExample) |
| MX (1) | MX2008013599A (enExample) |
| RU (1) | RU2008145871A (enExample) |
| WO (1) | WO2007124423A2 (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2009992B1 (en) | 2006-04-21 | 2012-06-27 | GlaxoSmithKline LLC | Il-8 receptor antagonists |
| MX2008013599A (es) | 2006-04-21 | 2008-10-31 | Smithkline Beechman Corp | Antagonistas del receptor il-8. |
| TW201035102A (en) * | 2009-03-04 | 2010-10-01 | Gruenethal Gmbh | Sulfonylated tetrahydroazolopyrazines and their use as medicinal products |
| JO3156B1 (ar) | 2009-07-09 | 2017-09-20 | Novartis Ag | ايميدازولات مدمجة والتركيبات التي تشملها لعلاج الأمراض الطفيلية على مثال الملاريا |
| CN102781448B (zh) * | 2010-03-01 | 2015-01-21 | 诺瓦药品公司 | 用于治疗病毒性疾病的组合物和方法 |
| US8648070B2 (en) * | 2010-12-17 | 2014-02-11 | Boehringer Ingelheim International Gmbh | Bicyclic ring system substituted sulfonamide functionalised phenols as medicaments |
| US8648118B2 (en) * | 2010-12-17 | 2014-02-11 | Boehringer Ingelheim International Gmbh | Bicyclic ring system substituted amide functionalised phenols as medicaments |
| US9241930B2 (en) | 2011-08-24 | 2016-01-26 | Novadrug, Llc | Compositions and methods for treating viral diseases |
| KR20150002713A (ko) | 2012-03-28 | 2015-01-07 | 뉴로포레 테라피스, 인코포레이티드 | 단백질 응집 저해제로서의 페닐-우레아 및 페닐-카바메이트 유도체 |
| US10167293B2 (en) * | 2016-05-26 | 2019-01-01 | Bayer Pharma Aktiengesellschaft | [8-(phenylsulfonyl)-3,8-diazabicyclo[3.2.1]oct-3-yl](1H-1,2,3-triazol-4-yl)methanones |
| EA036824B1 (ru) * | 2016-07-11 | 2020-12-24 | Байер Фарма Акциенгезельшафт | [8-(фенилсульфонил)-3,8-диазабицикло[3.2.1]окт-3-ил](1н-1,2,3-триазол-4-ил)метаноны |
| AU2018235937A1 (en) * | 2017-03-15 | 2019-09-19 | Lunella Biotech, Inc. | Mitoriboscins: mitochondrial-based therapeutics targeting cancer cells, bacteria, and pathogenic yeast |
| EP3615030A1 (en) | 2017-04-24 | 2020-03-04 | Novartis AG | Therapeutic regimen of 2-amino-l-(2-(4-fluorophenyl)-3-(4-fluorophenylamino)-8,8-dimethyl-5,6-dihydroimidazo[1,2-a]pyrazin-7(8h)-yl)ethanone and combinations thereof |
| US11136315B2 (en) | 2018-01-11 | 2021-10-05 | Medshine Discovery Inc. | CXCR2 antagonist |
| WO2021004531A1 (zh) * | 2019-07-11 | 2021-01-14 | 南京明德新药研发有限公司 | 一种cxcr2拮抗剂的晶型及其应用 |
Family Cites Families (100)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1792156A (en) | 1928-01-17 | 1931-02-10 | Gen Aniline Works Inc | 5-halogen-2-amino-1-alkyloxy and 1-aralkyloxy-benzenes and intermediate products thereof and process of preparing them |
| US2363074A (en) | 1938-06-16 | 1944-11-21 | Geigy Ag J R | Halogen substituted acylamino sulphonic acids of the aromatic series and their manufacture |
| US2407309A (en) | 1942-02-04 | 1946-09-10 | Squibb & Sons Inc | Chemotherapeutic agents of the sulphonamide type |
| US2795610A (en) | 1955-03-31 | 1957-06-11 | Du Pont | Hydroxy-phenyl alkyl ureas |
| BE639588A (enExample) | 1962-11-06 | |||
| US3996253A (en) | 1966-01-11 | 1976-12-07 | Minnesota Mining And Manufacturing Company | Process for the preparation of color images |
| GB1210596A (en) | 1967-04-06 | 1970-10-28 | Armour Grocery Products Compan | Antiseptic compositions |
| CH506240A (de) | 1969-02-04 | 1971-04-30 | Ciba Geigy Ag | Verwendung von N-Hydroxyphenyl-N'-phenylharnstoffen zur Bekämpfung schädlicher Mikroorganismen ausserhalb der Textilindustrie |
| SE370866B (enExample) | 1968-03-21 | 1974-11-04 | Ciba Geigy Ag | |
| US3647819A (en) | 1969-09-19 | 1972-03-07 | Sterling Drug Inc | Indazolylphenylureas and indazolyl-phenylthioureas |
| FR2100943A1 (en) | 1970-07-23 | 1972-03-24 | Ici Ltd | O-carboylcarbanilides from anthranilic acid and substd - isocyanates - immuno-suppressive agents |
| US4048333A (en) | 1971-08-23 | 1977-09-13 | Medizinska Akademia | Method for treating a picorna virus infection |
| DE2303761A1 (de) | 1973-01-26 | 1974-08-01 | Henkel & Cie Gmbh | Neue n,n'-disubstituierte thioharnstoffe, deren herstellung sowie verwendung als antimikrobielle substanzen |
| US4008326A (en) | 1973-12-26 | 1977-02-15 | The Upjohn Company | Substituted ureas and thioureas and pharmaceutical compositions thereof |
| US3932434A (en) | 1974-08-30 | 1976-01-13 | Eli Lilly And Company | N-2-(6-hydroxybenzothiazolyl)-N'-phenyl (or substituted phenyl) ureas |
| JPS5598152A (en) | 1979-01-16 | 1980-07-25 | Hokko Chem Ind Co Ltd | Phenylurea derivative |
| DE2928485A1 (de) | 1979-07-14 | 1981-01-29 | Bayer Ag | Verwendung von harnstoffderivaten als arzneimittel bei der behandlung von fettstoffwechselstoerungen |
| GB2079480B (en) | 1980-07-08 | 1984-05-16 | Kodak Ltd | Heat-activated photographic and thermal recording processes employing precursor compounds |
| US4608205A (en) | 1983-03-09 | 1986-08-26 | American Cyanamid Company | Polyanionic benzene ureas |
| US4591604A (en) | 1984-03-28 | 1986-05-27 | American Cyanamid Company | Method of inhibiting the complement system by administering multisulfonated naphthalene ureas |
| DE68911203T2 (de) | 1988-03-30 | 1994-04-14 | Warner Lambert Co | N-[[(2,6-disubstituierte)phenyl]N'- arylalkyl] Harnstoffe als antihypercholesterolemische und antiatherosclerotische Mittel. |
| US5215570A (en) | 1988-10-20 | 1993-06-01 | Ciba-Geigy Corporation | Sulfamoylphenylureas |
| US5290814A (en) | 1988-11-21 | 1994-03-01 | Burroughs Wellcome Co. | Anti-atherosclerotic diaryl compounds |
| US5206234A (en) | 1990-10-22 | 1993-04-27 | Merck & Co., Inc. | Benzolactam analogs as antagonists of cck |
| JPH05294935A (ja) | 1991-03-15 | 1993-11-09 | Green Cross Corp:The | アミノピリジン系化合物 |
| DK0625898T3 (da) | 1992-02-12 | 1996-06-03 | Janssen Cilag S P A | Liposom-piroxicamformuleringer |
| NZ250916A (en) | 1993-02-27 | 1995-08-28 | Nihon Nohyaku Co Ltd | N-heteroaryl-n'-phenylureas, their use as acat inhibitors |
| DK41193D0 (da) | 1993-04-07 | 1993-04-07 | Neurosearch As | Ionkanalaabnere |
| US5312831A (en) | 1993-05-12 | 1994-05-17 | American Cyanamid Company | Urethanes and ureas that induce cytokine production |
| CA2123728A1 (en) | 1993-05-21 | 1994-11-22 | Noriyoshi Sueda | Urea derivatives and their use as acat inhibitors |
| US5401758A (en) | 1993-10-07 | 1995-03-28 | Bristol-Myers Squibb Company | Pyridinyl cyanoguanidine compounds |
| US5547966A (en) | 1993-10-07 | 1996-08-20 | Bristol-Myers Squibb Company | Aryl urea and related compounds |
| US5441984A (en) | 1994-01-06 | 1995-08-15 | Eli Lilly And Company | Urea, thiourea and guanidine derivatives |
| US5576335A (en) | 1994-02-01 | 1996-11-19 | Nisshin Flour Milling Co., Ltd. | Urea derivatives and their use as ACAT inhibitors |
| DE4413265A1 (de) | 1994-04-16 | 1995-10-19 | Basf Ag | Hydroxyphenylharnstoffe |
| US5780483A (en) | 1995-02-17 | 1998-07-14 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| EP0809492A4 (en) | 1995-02-17 | 2007-01-24 | Smithkline Beecham Corp | IL-8 RECEPTOR ANTAGONISTS |
| US6005008A (en) | 1996-02-16 | 1999-12-21 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6211373B1 (en) | 1996-03-20 | 2001-04-03 | Smithkline Beecham Corporation | Phenyl urea antagonists of the IL-8 receptor |
| US6262113B1 (en) | 1996-03-20 | 2001-07-17 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| CZ425698A3 (cs) | 1996-06-27 | 1999-06-16 | Smithkline Beecham Corporation | Antagonista IL-8 receptoru |
| EP0932405A4 (en) | 1996-06-27 | 2001-10-17 | Smithkline Beckman Corp | IL-8 RECEPTOR ANTAGONISTS |
| TR199802694T2 (xx) | 1996-06-27 | 1999-03-22 | Smithkline Beecham Corporation | IL-8 resept�r kar��tlar� |
| WO1997049287A1 (en) | 1996-06-27 | 1997-12-31 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| WO1997049399A1 (en) | 1996-06-27 | 1997-12-31 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| JP2002513384A (ja) | 1996-08-06 | 2002-05-08 | スミスクライン・ビーチャム・コーポレイション | Ｉｌ―８受容体アンタゴニスト |
| WO1998005329A1 (en) | 1996-08-06 | 1998-02-12 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| WO1998005317A1 (en) | 1996-08-06 | 1998-02-12 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| JP2001527519A (ja) | 1996-08-15 | 2001-12-25 | スミスクライン・ビーチャム・コーポレイション | Ｉｌ―８レセプターアンタゴニスト |
| WO1998006398A1 (en) | 1996-08-15 | 1998-02-19 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| EP0923373A4 (en) | 1996-08-15 | 2001-10-17 | Smithkline Beecham Corp | IL-8 RECEPTOR ANTAGOISTS |
| WO1998006701A1 (en) | 1996-08-15 | 1998-02-19 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| AR008290A1 (es) | 1996-08-15 | 1999-12-29 | Smithkline Beecham Corp | Nuevos compuestos que contienen guanidina utiles como antagonistas de los receptores de il-8, composiciones farmaceuticas que los contienenprocedimiento para la preparacion de dichos compuestos y procedimiento para la preparacion de intermediarios. |
| JP2001501918A (ja) | 1996-08-21 | 2001-02-13 | スミスクライン・ビーチャム・コーポレイション | Ｉｌ―８レセプターアンタゴニスト |
| US5929250A (en) | 1997-01-23 | 1999-07-27 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| KR20000070368A (ko) | 1997-01-23 | 2000-11-25 | 스튜어트 알. 수터, 스티븐 베네티아너, 피터 존 기딩스 | 인터루킨-8 수용체 길항제 |
| US6436927B1 (en) | 1997-02-12 | 2002-08-20 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| AU8673198A (en) | 1997-07-29 | 1999-02-22 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| AR015425A1 (es) | 1997-09-05 | 2001-05-02 | Smithkline Beecham Corp | Compuestos de benzotiazol, composicion farmaceutica que los contiene, su uso en la manufactura de un medicamento, procedimiento para su preparacion,compuestos intermediarios y procedimiento para su preparacion |
| AR015426A1 (es) | 1997-09-05 | 2001-05-02 | Smithkline Beecham Corp | Compuestos de benzotiazol antagonistas del receptor de il-8, composicion farmaceutica que los contiene, su uso para la manufactura de un medicamento,procedimiento para su preparacion, compuestos intermediarios y procedimiento para su preparacion |
| JP2002509105A (ja) | 1998-01-16 | 2002-03-26 | スミスクライン・ビーチャム・コーポレイション | Ｉｌ−８受容体アンタゴニスト |
| WO1999036070A1 (en) | 1998-01-20 | 1999-07-22 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| WO2000006557A1 (en) | 1998-07-27 | 2000-02-10 | Smithkline Beecham Corporation | Novel process for making il-8 receptor antagonists |
| JP2003525856A (ja) | 1998-08-28 | 2003-09-02 | スミスクライン・ビーチャム・コーポレイション | ２−アミノ−５−シアノフェノールの製法 |
| CA2341718A1 (en) | 1998-08-28 | 2000-03-09 | Neil H. Baine | An improved synthesis of 3-hydroxy-4-amino-benzonitrile |
| NZ510435A (en) | 1998-09-23 | 2003-04-29 | Tularik Inc | Arylsulfonanilide ureas and pharmaceutical use |
| JP4213792B2 (ja) * | 1998-09-24 | 2009-01-21 | 日東電工株式会社 | 熱硬化型感圧性接着剤とその接着シ―ト類 |
| UY25842A1 (es) | 1998-12-16 | 2001-04-30 | Smithkline Beecham Corp | Antagonistas de receptores de il-8 |
| AR029637A1 (es) | 1999-05-28 | 2003-07-10 | Smithkline Beecham Corp | Compuestos de guanidina, antagonistas de los receptores de la il-8, una composicion farmaceutica que los contiene y el uso de los mismos para la manufactura de un medicamento |
| US20030225125A1 (en) | 1999-06-16 | 2003-12-04 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6372933B1 (en) | 1999-08-26 | 2002-04-16 | Smithkline Beecham Corporation | Process for preparing certain phenyl urea compounds |
| US6440993B1 (en) | 1999-10-12 | 2002-08-27 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| EP1274413A4 (en) | 2000-03-01 | 2005-08-10 | Smithkline Beecham Corp | IL-8 RECEPTOR ANTAGONISTS |
| MY133845A (en) | 2000-03-10 | 2007-11-30 | Smithkline Beecham Corp | Il-8 receptor antagonists |
| JP2004504270A (ja) | 2000-03-10 | 2004-02-12 | スミスクライン・ビーチャム・コーポレイション | Ｉｌ−８受容体アンタゴニスト |
| US6767922B2 (en) * | 2000-03-14 | 2004-07-27 | Smithkline Beecham Corporation | IL-8 receptor antagonists |
| US6664259B2 (en) * | 2000-03-16 | 2003-12-16 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| AR031098A1 (es) * | 2000-03-16 | 2003-09-10 | Smithkline Beecham Corp | Compuestos de hidroxifenil urea sustituidos con sulfonamidas, composiciones farmaceuticas que los comprenden, y uso de los mismos en la fabricacion de medicamentos para tratar una enfermedad mediada por una quimioquina |
| UY26627A1 (es) | 2000-03-24 | 2001-09-28 | Smithkline Beecham Corp | Antagonistas de receptores de il-8 |
| EP1274428A4 (en) | 2000-04-07 | 2003-05-02 | Smithkline Beecham Corp | INTERLEUKIN-8 (IL-8) RECEPTOR ANTAGONISTS |
| US6432960B2 (en) | 2000-05-10 | 2002-08-13 | Bristol-Myers Squibb Company | Squarate derivatives of dihydropyridine NPY antagonists |
| WO2001092202A1 (en) | 2000-05-30 | 2001-12-06 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| DE60230722D1 (de) | 2001-01-16 | 2009-02-26 | Smithkline Beecham Corp | Il-8-rezeptor-antagonisten |
| WO2002057230A1 (en) | 2001-01-16 | 2002-07-25 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| US20030204085A1 (en) | 2001-02-02 | 2003-10-30 | Taveras Arthur G. | 3, 4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor antagonists |
| PL367534A1 (en) | 2001-02-02 | 2005-02-21 | Schering Corporation | 3,4-di-substituted cyclobutene-1, 2-diones as cxc chemokine receptor antagonists |
| KR20030088044A (ko) | 2001-03-30 | 2003-11-15 | 스미스클라인 비참 코포레이션 | 페놀-함유 화합물의 합성 방법 |
| WO2002098869A2 (en) | 2001-06-05 | 2002-12-12 | Boehringer Ingelheim Pharmaceuticals, Inc. | 1,4-disubstituted benzo-fused cycloalkyl urea compounds |
| US20040038854A1 (en) | 2001-07-16 | 2004-02-26 | Dillon Susan B. | Use of il-8 receptor antagonists in the treatment of virus infections |
| US20030032802A1 (en) | 2002-08-30 | 2003-02-13 | Palovich Michael R. | IL8-receptor antagonists |
| US20030028042A1 (en) | 2002-08-30 | 2003-02-06 | Palovich Michael R. | Il8-receptor antagonists |
| US20030065170A1 (en) | 2002-09-05 | 2003-04-03 | Widdowson Katherine Louisa | Il-8 receptor antagonists |
| TW200418812A (en) | 2002-10-29 | 2004-10-01 | Smithkline Beecham Corp | IL-8 receptor antagonists |
| TW200510311A (en) * | 2002-12-23 | 2005-03-16 | Millennium Pharm Inc | CCr8 inhibitors |
| WO2005000231A2 (en) | 2003-06-06 | 2005-01-06 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| US20070249625A1 (en) | 2004-10-20 | 2007-10-25 | Jakob Busch-Petersen | Il-8 Receptor Antagonists |
| MX2008013599A (es) | 2006-04-21 | 2008-10-31 | Smithkline Beechman Corp | Antagonistas del receptor il-8. |
| EP2009992B1 (en) | 2006-04-21 | 2012-06-27 | GlaxoSmithKline LLC | Il-8 receptor antagonists |
| TW200817006A (en) | 2006-06-23 | 2008-04-16 | Smithkline Beecham Corp | IL-8 receptor antagonist |
| EP2099300A4 (en) | 2006-12-05 | 2011-12-07 | Glaxosmithkline Llc | IL-8 RECEPTOR ANTAGONISTS |
-
2007
- 2007-04-20 MX MX2008013599A patent/MX2008013599A/es not_active Application Discontinuation
- 2007-04-20 US US12/297,917 patent/US8097626B2/en not_active Expired - Fee Related
- 2007-04-20 AU AU2007240364A patent/AU2007240364A1/en not_active Abandoned
- 2007-04-20 CN CNA2007800232115A patent/CN101495113A/zh active Pending
- 2007-04-20 CA CA002650007A patent/CA2650007A1/en not_active Abandoned
- 2007-04-20 WO PCT/US2007/067088 patent/WO2007124423A2/en not_active Ceased
- 2007-04-20 EP EP07761016A patent/EP2010180A4/en not_active Withdrawn
- 2007-04-20 BR BRPI0710559-2A patent/BRPI0710559A2/pt not_active IP Right Cessation
- 2007-04-20 RU RU2008145871/04A patent/RU2008145871A/ru not_active Application Discontinuation
- 2007-04-20 JP JP2009506793A patent/JP2009534420A/ja active Pending
-
2008
- 2008-10-12 IL IL194700A patent/IL194700A0/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009534420A5 (enExample) | ||
| RU2008145871A (ru) | Антагонисты рецептора il-8 | |
| US10487079B2 (en) | Heteroaryl carboxamides | |
| CA2481482C (en) | Tropane derivatives as ccr5 modulators | |
| JP2009534421A5 (enExample) | ||
| EP1966200B1 (en) | Heterocyclic janus kinase 3 inhibitors | |
| US8124600B2 (en) | 5-HT3 receptor modulators, methods of making, and use thereof | |
| CA2402039A1 (en) | 3-(diarylmethylene)-8-azabicyclo[3.2.1]octane derivatives | |
| US20050107460A1 (en) | Bicyclic n-arylamides | |
| JPWO2010119875A1 (ja) | 縮合ピロロピリジン誘導体 | |
| WO2020239660A1 (en) | Novel compounds and pharmaceutical compositions thereof for the treatment of diseases | |
| RU2010107795A (ru) | Бициклические амиды для усиления глутаматергических синаптических ответов | |
| CN102056933A (zh) | 作为白三烯a4水解酶调节剂的噻唑并吡啶-2-基氧基-苯基和噻唑并吡嗪-2-基氧基-苯基胺类 | |
| JP2007518740A (ja) | ムスカリン性アセチルコリン受容体アンタゴニスト | |
| US20070185157A1 (en) | Tropane derivatives useful in therapy | |
| RU2009135834A (ru) | Кристаллические формы соединения 8-азабицикло(3.2.1)октана | |
| AU2003281527A1 (en) | Bicyclic piperidine derivatives as antagonists of the ccr1 chemokine receptor | |
| EP2344496A1 (en) | Amides of diazabicyclooctanes and uses thereof | |
| JP2007534678A5 (enExample) | ||
| WO2025132358A1 (en) | Novel compounds and pharmaceutical compositions thereof for the treatment of infectious diseases | |
| US20050004163A1 (en) | 3-(diarylmethylene)-8-azabicyclo[3.2.1]octane derivatives | |
| RU2021118626A (ru) | Производные 7-фенокси-n-(3-азабицикло[3.2.1]октан-8-ил)-6,7-дигидро-5h-пирроло[1,2-b][1,2,4]триазол-2-амина и связанные соединения в качестве модуляторов гамма-секретазы для лечения болезни альцгеймера | |
| MXPA06007958A (en) | Muscarinic acetylcholine receptor antagonists |