OA11731A - Hydroxy diphenyl urea sulfonamides as IL-8 receptor antagonists. - Google Patents
Hydroxy diphenyl urea sulfonamides as IL-8 receptor antagonists. Download PDFInfo
- Publication number
- OA11731A OA11731A OA1200100154A OA1200100154A OA11731A OA 11731 A OA11731 A OA 11731A OA 1200100154 A OA1200100154 A OA 1200100154A OA 1200100154 A OA1200100154 A OA 1200100154A OA 11731 A OA11731 A OA 11731A
- Authority
- OA
- OAPI
- Prior art keywords
- urea
- chloro
- hydroxy
- aminosulfonyl
- dichlorophenyl
- Prior art date
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- -1 Hydroxy diphenyl urea sulfonamides Chemical class 0.000 title claims abstract description 81
- 229940124530 sulfonamide Drugs 0.000 title abstract description 53
- 102000010681 interleukin-8 receptors Human genes 0.000 title description 6
- 108010038415 interleukin-8 receptors Proteins 0.000 title description 5
- 239000002464 receptor antagonist Substances 0.000 title 1
- 229940044551 receptor antagonist Drugs 0.000 title 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 726
- 239000004202 carbamide Substances 0.000 claims description 378
- 238000000034 method Methods 0.000 claims description 272
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 137
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 103
- 125000000217 alkyl group Chemical group 0.000 claims description 82
- 229910052739 hydrogen Inorganic materials 0.000 claims description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 72
- 150000001875 compounds Chemical class 0.000 claims description 72
- 239000001257 hydrogen Substances 0.000 claims description 67
- 125000003118 aryl group Chemical group 0.000 claims description 55
- 125000001072 heteroaryl group Chemical group 0.000 claims description 52
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 48
- 125000000623 heterocyclic group Chemical group 0.000 claims description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 41
- 230000007062 hydrolysis Effects 0.000 claims description 40
- 238000006460 hydrolysis reaction Methods 0.000 claims description 40
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 28
- 125000003545 alkoxy group Chemical group 0.000 claims description 25
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 150000002431 hydrogen Chemical group 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 17
- 229910052708 sodium Inorganic materials 0.000 claims description 15
- 239000011734 sodium Substances 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 11
- 125000003107 substituted aryl group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 8
- VYWQTJWGWLKBQA-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;chloride Chemical compound Cl.NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-N 0.000 claims description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 8
- 229910017604 nitric acid Inorganic materials 0.000 claims description 8
- 239000012312 sodium hydride Substances 0.000 claims description 8
- WTLRWOHEKQGKDS-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-sulfamoylphenyl)-3-(2,3-dichlorophenyl)urea Chemical compound NS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1O WTLRWOHEKQGKDS-UHFFFAOYSA-N 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- USJRACJWHFMFOU-UHFFFAOYSA-N 1-[3-[bis(2-methoxyethyl)sulfamoyl]-4-chloro-2-hydroxyphenyl]-3-(2,3-dichlorophenyl)urea Chemical compound COCCN(CCOC)S(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1O USJRACJWHFMFOU-UHFFFAOYSA-N 0.000 claims description 5
- ZEJUGAOSIALXKD-UHFFFAOYSA-N 1-[4-chloro-2-hydroxy-3-[(1-oxo-1,4-thiazinan-4-yl)sulfonyl]phenyl]-3-(2,3-dichlorophenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CCS(=O)CC2)C(O)=C1NC(=O)NC1=CC=CC(Cl)=C1Cl ZEJUGAOSIALXKD-UHFFFAOYSA-N 0.000 claims description 5
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 claims description 5
- 150000001540 azides Chemical class 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- YWFVGENQTSRXGG-UHFFFAOYSA-N 1-[4-chloro-2-hydroxy-3-[methoxy(methyl)sulfamoyl]phenyl]-3-(2,3-dichlorophenyl)urea Chemical compound CON(C)S(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1O YWFVGENQTSRXGG-UHFFFAOYSA-N 0.000 claims description 4
- CRUWUHMDYZKBQL-UHFFFAOYSA-N 6-[[6-chloro-3-[(2,3-dichlorophenyl)carbamoylamino]-2-hydroxyphenyl]sulfonylamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CCCCNS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1O CRUWUHMDYZKBQL-UHFFFAOYSA-N 0.000 claims description 4
- IOOZIXMHHDXUIJ-UHFFFAOYSA-N 6-[[6-chloro-3-[(2-chlorophenyl)carbamoylamino]-2-hydroxyphenyl]sulfonylamino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoic acid Chemical compound CC(C)(C)OC(=O)NC(C(O)=O)CCCCNS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=CC=CC=2)Cl)=C1O IOOZIXMHHDXUIJ-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000006261 methyl amino sulfonyl group Chemical group [H]N(C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
- BPBATAFSRWQKGT-UHFFFAOYSA-N tert-butyl 4-[[[3-[(2-bromophenyl)carbamoylamino]-6-chloro-2-hydroxyphenyl]sulfonylamino]methyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CNS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=CC=CC=2)Br)=C1O BPBATAFSRWQKGT-UHFFFAOYSA-N 0.000 claims description 4
- IJLFVSFRJXOQAC-UHFFFAOYSA-N tert-butyl 4-[[[6-chloro-3-[(2,3-dichlorophenyl)carbamoylamino]-2-hydroxyphenyl]sulfonylamino]methyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CNS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1O IJLFVSFRJXOQAC-UHFFFAOYSA-N 0.000 claims description 4
- LRPZJUYRWLMIME-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[4-chloro-2-hydroxy-3-(2-morpholin-4-ylethylsulfamoyl)phenyl]urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)NCCN2CCOCC2)C(O)=C1NC(=O)NC1=CC=CC=C1Br LRPZJUYRWLMIME-UHFFFAOYSA-N 0.000 claims description 3
- QTYAKDWUWAUTKB-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[4-chloro-2-hydroxy-3-(piperidin-4-ylmethylsulfamoyl)phenyl]urea;hydrochloride Chemical compound Cl.C1=CC(Cl)=C(S(=O)(=O)NCC2CCNCC2)C(O)=C1NC(=O)NC1=CC=CC=C1Br QTYAKDWUWAUTKB-UHFFFAOYSA-N 0.000 claims description 3
- TUBUYQNHCVSORA-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[4-chloro-3-[2-(dimethylamino)ethylsulfamoyl]-2-hydroxyphenyl]urea;hydrochloride Chemical compound Cl.CN(C)CCNS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=CC=CC=2)Br)=C1O TUBUYQNHCVSORA-UHFFFAOYSA-N 0.000 claims description 3
- DVJNRBFRDKWRGZ-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-morpholin-4-ylsulfonylphenyl)-3-(2,3-dichlorophenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CCOCC2)C(O)=C1NC(=O)NC1=CC=CC(Cl)=C1Cl DVJNRBFRDKWRGZ-UHFFFAOYSA-N 0.000 claims description 3
- CYFLBYNPTBOTBA-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-sulfamoylphenyl)-3-(2,3-dichlorophenyl)urea;sodium Chemical compound [Na].NS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1O CYFLBYNPTBOTBA-UHFFFAOYSA-N 0.000 claims description 3
- FREATZYVHXVRFE-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-sulfamoylphenyl)-3-(2-chlorophenyl)urea Chemical compound NS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=CC=CC=2)Cl)=C1O FREATZYVHXVRFE-UHFFFAOYSA-N 0.000 claims description 3
- ZKTJMPNHMFVMRB-UHFFFAOYSA-N 1-[3-(3-aminopropylsulfamoyl)-4-chloro-2-hydroxyphenyl]-3-(2,3-dichlorophenyl)urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NCCCNS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1O ZKTJMPNHMFVMRB-UHFFFAOYSA-N 0.000 claims description 3
- VUYRFCQHUYFDPC-UHFFFAOYSA-N 1-[3-(3-aminopropylsulfamoyl)-4-chloro-2-hydroxyphenyl]-3-(2-bromophenyl)urea;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.NCCCNS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=CC=CC=2)Br)=C1O VUYRFCQHUYFDPC-UHFFFAOYSA-N 0.000 claims description 3
- FYUYZAISOBJBKN-UHFFFAOYSA-N 1-[3-(3-aminopropylsulfamoyl)-4-chloro-2-hydroxyphenyl]-3-(2-bromophenyl)urea;hydrochloride Chemical compound Cl.NCCCNS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=CC=CC=2)Br)=C1O FYUYZAISOBJBKN-UHFFFAOYSA-N 0.000 claims description 3
- IHDKSFQUTBZHIG-UHFFFAOYSA-N 1-[3-(azetidin-1-ylsulfonyl)-4-chloro-2-hydroxyphenyl]-3-(2-bromophenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CCC2)C(O)=C1NC(=O)NC1=CC=CC=C1Br IHDKSFQUTBZHIG-UHFFFAOYSA-N 0.000 claims description 3
- REKHAVCDCMAEDI-UHFFFAOYSA-N 1-[3-[bis(2-hydroxyethyl)sulfamoyl]-4-chloro-2-hydroxyphenyl]-3-(2,3-dichlorophenyl)urea Chemical compound OCCN(CCO)S(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1O REKHAVCDCMAEDI-UHFFFAOYSA-N 0.000 claims description 3
- KSUOUYHJVXMOBZ-UHFFFAOYSA-N 1-[3-[bis(2-methoxyethyl)sulfamoyl]-4-chloro-2-hydroxyphenyl]-3-(2-bromophenyl)urea Chemical compound COCCN(CCOC)S(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=CC=CC=2)Br)=C1O KSUOUYHJVXMOBZ-UHFFFAOYSA-N 0.000 claims description 3
- MHQPTTGNFCCOQQ-UHFFFAOYSA-N 1-[4-chloro-2-hydroxy-3-(2-morpholin-4-ylethylsulfamoyl)phenyl]-3-(2,3-dichlorophenyl)urea;hydrochloride Chemical compound Cl.C1=CC(Cl)=C(S(=O)(=O)NCCN2CCOCC2)C(O)=C1NC(=O)NC1=CC=CC(Cl)=C1Cl MHQPTTGNFCCOQQ-UHFFFAOYSA-N 0.000 claims description 3
- BIVRGLRQQDPKSJ-UHFFFAOYSA-N 1-[4-chloro-2-hydroxy-3-(2-morpholin-4-ylethylsulfamoyl)phenyl]-3-(2-chlorophenyl)urea;hydrochloride Chemical compound Cl.C1=CC(Cl)=C(S(=O)(=O)NCCN2CCOCC2)C(O)=C1NC(=O)NC1=CC=CC=C1Cl BIVRGLRQQDPKSJ-UHFFFAOYSA-N 0.000 claims description 3
- QQZSWRALACIVKN-UHFFFAOYSA-N 1-[4-chloro-2-hydroxy-3-(2-propan-2-yloxyethylsulfamoyl)phenyl]-3-(2-chlorophenyl)urea Chemical compound CC(C)OCCNS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=CC=CC=2)Cl)=C1O QQZSWRALACIVKN-UHFFFAOYSA-N 0.000 claims description 3
- RVTUWWCROPRUCB-UHFFFAOYSA-N 1-[4-chloro-2-hydroxy-3-[methoxy(methyl)sulfamoyl]phenyl]-3-(2-chlorophenyl)urea Chemical compound CON(C)S(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=CC=CC=2)Cl)=C1O RVTUWWCROPRUCB-UHFFFAOYSA-N 0.000 claims description 3
- XYOJBTIUANAJMO-UHFFFAOYSA-N 1-[4-chloro-3-(cyclopropylmethylsulfamoyl)-2-hydroxyphenyl]-3-(2,3-dichlorophenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)NCC2CC2)C(O)=C1NC(=O)NC1=CC=CC(Cl)=C1Cl XYOJBTIUANAJMO-UHFFFAOYSA-N 0.000 claims description 3
- FSTISGLVJFANFN-UHFFFAOYSA-N 1-[4-chloro-3-(cyclopropylmethylsulfamoyl)-2-hydroxyphenyl]-3-(2-chlorophenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)NCC2CC2)C(O)=C1NC(=O)NC1=CC=CC=C1Cl FSTISGLVJFANFN-UHFFFAOYSA-N 0.000 claims description 3
- KCFSDULZVWHBCZ-UHFFFAOYSA-N 1-[4-chloro-3-[(1,1-dioxo-1,4-thiazinan-4-yl)sulfonyl]-2-hydroxyphenyl]-3-(2,3-dichlorophenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CCS(=O)(=O)CC2)C(O)=C1NC(=O)NC1=CC=CC(Cl)=C1Cl KCFSDULZVWHBCZ-UHFFFAOYSA-N 0.000 claims description 3
- GSPVITUWQGKNKA-UHFFFAOYSA-N 2-amino-6-[[6-chloro-3-[(2-chlorophenyl)carbamoylamino]-2-hydroxyphenyl]sulfonylamino]hexanoic acid;hydrochloride Chemical compound Cl.OC(=O)C(N)CCCCNS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=CC=CC=2)Cl)=C1O GSPVITUWQGKNKA-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000001632 sodium acetate Substances 0.000 claims description 3
- 235000017281 sodium acetate Nutrition 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- IJBIKBBICMCEHH-UHFFFAOYSA-N tert-butyl n-[3-[[3-[(2-bromophenyl)carbamoylamino]-6-chloro-2-hydroxyphenyl]sulfonylamino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=CC=CC=2)Br)=C1O IJBIKBBICMCEHH-UHFFFAOYSA-N 0.000 claims description 3
- CGKPKSCYSRNXPY-UHFFFAOYSA-N (2,3-dichlorophenyl)urea hydrochloride Chemical compound Cl.NC(=O)Nc1cccc(Cl)c1Cl CGKPKSCYSRNXPY-UHFFFAOYSA-N 0.000 claims description 2
- AZCYJEGLRSHUQN-UHFFFAOYSA-N 1-(2-bromo-3-fluorophenyl)-3-(4-chloro-2-hydroxy-3-sulfamoylphenyl)urea Chemical compound NS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=C(F)C=CC=2)Br)=C1O AZCYJEGLRSHUQN-UHFFFAOYSA-N 0.000 claims description 2
- KDXMZVRLUDLWSB-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(4-chloro-2-hydroxy-3-morpholin-4-ylsulfonylphenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CCOCC2)C(O)=C1NC(=O)NC1=CC=CC=C1Br KDXMZVRLUDLWSB-UHFFFAOYSA-N 0.000 claims description 2
- BICMBSXXKPGUGQ-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(4-chloro-2-hydroxy-3-thiomorpholin-4-ylsulfonylphenyl)urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CCSCC2)C(O)=C1NC(=O)NC1=CC=CC=C1Br BICMBSXXKPGUGQ-UHFFFAOYSA-N 0.000 claims description 2
- MSMYXJWMCQMKJZ-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[4-chloro-2-hydroxy-3-(1,2-oxazolidin-3-ylsulfamoyl)phenyl]urea Chemical compound BrC1=C(C=CC=C1)NC(=O)NC1=C(C(=C(C=C1)Cl)S(=O)(=O)NC1NOCC1)O MSMYXJWMCQMKJZ-UHFFFAOYSA-N 0.000 claims description 2
- QBBXUGZXUXMDHU-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[4-chloro-2-hydroxy-3-(2-methoxyethylsulfamoyl)phenyl]urea Chemical compound COCCNS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=CC=CC=2)Br)=C1O QBBXUGZXUXMDHU-UHFFFAOYSA-N 0.000 claims description 2
- XTMOHOUEIHSHBP-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[4-chloro-2-hydroxy-3-(2-propan-2-yloxyethylsulfamoyl)phenyl]urea Chemical compound CC(C)OCCNS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=CC=CC=2)Br)=C1O XTMOHOUEIHSHBP-UHFFFAOYSA-N 0.000 claims description 2
- LTSABOCZIXUPKO-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[4-chloro-2-hydroxy-3-(3-methylsulfanylpropylsulfamoyl)phenyl]urea Chemical compound CSCCCNS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=CC=CC=2)Br)=C1O LTSABOCZIXUPKO-UHFFFAOYSA-N 0.000 claims description 2
- QCCWUHLFZSAWAP-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[4-chloro-2-hydroxy-3-[(1-oxo-1,4-thiazinan-4-yl)sulfonyl]phenyl]urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CCS(=O)CC2)C(O)=C1NC(=O)NC1=CC=CC=C1Br QCCWUHLFZSAWAP-UHFFFAOYSA-N 0.000 claims description 2
- DVAPHBXKXWATMJ-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[4-chloro-3-(cyclopropylmethylsulfamoyl)-2-hydroxyphenyl]urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)NCC2CC2)C(O)=C1NC(=O)NC1=CC=CC=C1Br DVAPHBXKXWATMJ-UHFFFAOYSA-N 0.000 claims description 2
- WQDFUCNPEBWLIG-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[4-chloro-3-[(1,1-dioxo-1,4-thiazinan-4-yl)sulfonyl]-2-hydroxyphenyl]urea Chemical compound C1=CC(Cl)=C(S(=O)(=O)N2CCS(=O)(=O)CC2)C(O)=C1NC(=O)NC1=CC=CC=C1Br WQDFUCNPEBWLIG-UHFFFAOYSA-N 0.000 claims description 2
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- HQBCIDPLKYTXIR-UHFFFAOYSA-N tert-butyl 4-(2,6-dichloro-3-nitrophenyl)sulfonylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1S(=O)(=O)C1=C(Cl)C=CC([N+]([O-])=O)=C1Cl HQBCIDPLKYTXIR-UHFFFAOYSA-N 0.000 description 1
- LCIACHWXRVKXPA-UHFFFAOYSA-N tert-butyl 4-[3-[(2-bromophenyl)carbamoylamino]-6-chloro-2-hydroxyphenyl]sulfonylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1S(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=CC=CC=2)Br)=C1O LCIACHWXRVKXPA-UHFFFAOYSA-N 0.000 description 1
- KELRDEGJZFWPKY-UHFFFAOYSA-N tert-butyl 4-[6-chloro-3-[(2,3-dichlorophenyl)carbamoylamino]-2-hydroxyphenyl]sulfonylpiperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1S(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=C(Cl)C=CC=2)Cl)=C1O KELRDEGJZFWPKY-UHFFFAOYSA-N 0.000 description 1
- MPVWZTNFECENRY-UHFFFAOYSA-N tert-butyl 4-[[(2,6-dichloro-3-nitrophenyl)sulfonylamino]methyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CNS(=O)(=O)C1=C(Cl)C=CC([N+]([O-])=O)=C1Cl MPVWZTNFECENRY-UHFFFAOYSA-N 0.000 description 1
- IRMMSJCFVWGLCP-UHFFFAOYSA-N tert-butyl 4-[[(3-amino-6-chloro-2-hydroxyphenyl)sulfonylamino]methyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CNS(=O)(=O)C1=C(Cl)C=CC(N)=C1O IRMMSJCFVWGLCP-UHFFFAOYSA-N 0.000 description 1
- KJSBJMCSIVWJNJ-UHFFFAOYSA-N tert-butyl 4-[[(6-chloro-2-hydroxy-3-nitrophenyl)sulfonylamino]methyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1CNS(=O)(=O)C1=C(O)C([N+]([O-])=O)=CC=C1Cl KJSBJMCSIVWJNJ-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AOCSUUGBCMTKJH-UHFFFAOYSA-N tert-butyl n-(2-aminoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCN AOCSUUGBCMTKJH-UHFFFAOYSA-N 0.000 description 1
- POHWAQLZBIMPRN-UHFFFAOYSA-N tert-butyl n-(3-aminopropyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCCN POHWAQLZBIMPRN-UHFFFAOYSA-N 0.000 description 1
- GOLJVCMLYOCUQA-UHFFFAOYSA-N tert-butyl n-[2-[(6-chloro-2-hydroxy-3-nitrophenyl)sulfonylamino]ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCNS(=O)(=O)C1=C(O)C([N+]([O-])=O)=CC=C1Cl GOLJVCMLYOCUQA-UHFFFAOYSA-N 0.000 description 1
- HNHMDGDVHJYGFJ-UHFFFAOYSA-N tert-butyl n-[2-[[3-[(2-bromophenyl)carbamoylamino]-6-chloro-2-hydroxyphenyl]sulfonylamino]ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCNS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=CC=CC=2)Br)=C1O HNHMDGDVHJYGFJ-UHFFFAOYSA-N 0.000 description 1
- TZIWVEPCFXAYOY-UHFFFAOYSA-N tert-butyl n-[3-[(2,6-dichloro-3-nitrophenyl)sulfonylamino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNS(=O)(=O)C1=C(Cl)C=CC([N+]([O-])=O)=C1Cl TZIWVEPCFXAYOY-UHFFFAOYSA-N 0.000 description 1
- CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000005000 thioaryl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 241001529453 unidentified herpesvirus Species 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- GSQBIOQCECCMOQ-UHFFFAOYSA-N β-alanine ethyl ester Chemical compound CCOC(=O)CCN GSQBIOQCECCMOQ-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
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- C07D207/48—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
- C07D211/28—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/04—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/14—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
- C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Virology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Immunology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Dermatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
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- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Urology & Nephrology (AREA)
- Psychiatry (AREA)
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- Tropical Medicine & Parasitology (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11248198P | 1998-12-16 | 1998-12-16 | |
| US13700399P | 1999-06-01 | 1999-06-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA11731A true OA11731A (en) | 2005-05-12 |
Family
ID=26810001
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200100154A OA11731A (en) | 1998-12-16 | 1999-12-15 | Hydroxy diphenyl urea sulfonamides as IL-8 receptor antagonists. |
Country Status (32)
| Country | Link |
|---|---|
| US (2) | US6500863B1 (fr) |
| EP (1) | EP1161232B1 (fr) |
| JP (1) | JP2002532419A (fr) |
| KR (1) | KR20010101243A (fr) |
| CN (1) | CN1334726A (fr) |
| AR (1) | AR029605A1 (fr) |
| AT (1) | ATE262328T1 (fr) |
| AU (1) | AU748799B2 (fr) |
| BG (1) | BG105661A (fr) |
| BR (1) | BR9916159A (fr) |
| CA (1) | CA2355890A1 (fr) |
| CO (1) | CO4990929A1 (fr) |
| CZ (1) | CZ20012150A3 (fr) |
| DE (1) | DE69915888T2 (fr) |
| DK (1) | DK1161232T3 (fr) |
| DZ (1) | DZ2964A1 (fr) |
| EA (1) | EA005210B1 (fr) |
| ES (1) | ES2217871T3 (fr) |
| HK (1) | HK1043535B (fr) |
| HU (1) | HUP0104686A3 (fr) |
| IL (1) | IL143507A0 (fr) |
| MA (1) | MA25366A1 (fr) |
| NO (1) | NO20012948L (fr) |
| NZ (1) | NZ511993A (fr) |
| OA (1) | OA11731A (fr) |
| PE (1) | PE20001323A1 (fr) |
| PL (1) | PL348179A1 (fr) |
| PT (1) | PT1161232E (fr) |
| SK (1) | SK8222001A3 (fr) |
| TR (1) | TR200101772T2 (fr) |
| UY (1) | UY25842A1 (fr) |
| WO (1) | WO2000035442A1 (fr) |
Families Citing this family (60)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7517880B2 (en) * | 1997-12-22 | 2009-04-14 | Bayer Pharmaceuticals Corporation | Inhibition of p38 kinase using symmetrical and unsymmetrical diphenyl ureas |
| RU2319693C9 (ru) | 1999-01-13 | 2008-08-20 | Байер Копэрейшн | Производные мочевины (варианты), фармацевтическая композиция (варианты) и способ лечения заболевания, связанного с ростом раковых клеток (варианты) |
| EP1140840B1 (fr) * | 1999-01-13 | 2006-03-22 | Bayer Pharmaceuticals Corp. | Diphenylurees a substituants -g(v)-carboxyaryles, inhibitrices de kinase raf |
| US8124630B2 (en) | 1999-01-13 | 2012-02-28 | Bayer Healthcare Llc | ω-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| ATE538794T1 (de) | 1999-01-13 | 2012-01-15 | Bayer Healthcare Llc | Gamma carboxyarylsubstituierte diphenylharnstoffverbindungen als p38 kinasehemmer |
| 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 |
| EP1265905A4 (fr) * | 2000-03-01 | 2003-03-12 | Smithkline Beecham Corp | Antagonistes du recepteur de l'interleukine 8 (il-8) |
| 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 |
| MY133845A (en) * | 2000-03-10 | 2007-11-30 | Smithkline Beecham Corp | Il-8 receptor antagonists |
| AU2001245724A1 (en) * | 2000-03-14 | 2001-09-24 | Smith Kline Beecham Corporation | Il-8 receptor antagonists |
| AR030689A1 (es) * | 2000-03-14 | 2003-09-03 | Smithkline Beecham Corp | Compuestos de 3-aminosulfonil-2-hidroxifenil urea, composiciones farmaceuticas que los comprenden, y uso de dichos compuestos en la manufactura de medicamentos para tratar enfermedades mediadas por quimioquinas |
| CO5280089A1 (es) * | 2000-03-16 | 2003-05-30 | Smithkline Beecham Corp | Antagonistas del receptor il-8 |
| US6664259B2 (en) * | 2000-03-16 | 2003-12-16 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| UY26627A1 (es) * | 2000-03-24 | 2001-09-28 | Smithkline Beecham Corp | Antagonistas de receptores de il-8 |
| JP2003530328A (ja) | 2000-04-07 | 2003-10-14 | 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 |
| US6414161B1 (en) * | 2000-08-09 | 2002-07-02 | Boehringer Ingelheim Pharmaceuticals, Inc. | Synthesis of (R)-3-(4-Bromobenzyl)-1-(3,5-dichlorophenyl)-5-iodo-3-methyl-1-H-imidazo[1,2-a]imidazol-2-one |
| CN101849953B (zh) * | 2000-12-18 | 2012-04-25 | 株式会社医药分子设计研究所 | 炎症性细胞因子产生游离抑制剂 |
| EP1351933B1 (fr) * | 2001-01-16 | 2006-11-22 | SmithKline Beecham Corporation | Antagonistes des recepteurs de l'il-8 |
| CA2442480A1 (fr) * | 2001-03-30 | 2002-10-10 | Katherine L. Widdowson | Procedes de synthese de composes contenant un phenol |
| TW200303742A (en) | 2001-11-21 | 2003-09-16 | Novartis Ag | Organic compounds |
| US20030207872A1 (en) * | 2002-01-11 | 2003-11-06 | Bayer Corporation | Omega-carboxyaryl substituted diphenyl ureas as raf kinase inhibitors |
| US7838541B2 (en) | 2002-02-11 | 2010-11-23 | Bayer Healthcare, Llc | Aryl ureas with angiogenesis inhibiting activity |
| WO2003103647A1 (fr) * | 2002-06-05 | 2003-12-18 | 株式会社医薬分子設計研究所 | Inhibiteurs de l'activation de ap-1 et de nfat |
| AU2003242118B2 (en) | 2002-06-06 | 2008-09-11 | Institute Of Medicinal Molecular Design, Inc | O-substituted hydroxyaryl derivatives |
| WO2009039091A1 (fr) * | 2007-09-21 | 2009-03-26 | Smithkline Beecham Corporation | Procédé de traitement |
| AR041834A1 (es) * | 2002-10-29 | 2005-06-01 | Smithkline Beecham Corp | Compuesto de difenilurea sustituido con sulfonamida, composicion farmaceutica que lo comprende y su uso para preparar dicha composicion |
| UY28213A1 (es) | 2003-02-28 | 2004-09-30 | Bayer Pharmaceuticals Corp | Nuevos derivados de cianopiridina útiles en el tratamiento de cáncer y otros trastornos. |
| WO2004113274A2 (fr) | 2003-05-20 | 2004-12-29 | Bayer Pharmaceuticals Corporation | Diaryl-urees presentant une activite d'inhibition des kinases |
| RS52625B (sr) | 2003-07-23 | 2013-06-28 | Bayer Healthcare Llc | Fluoro supstituisana omega-karboksiaril difenil urea za lečenje i prevenciju bolesti i stanja bolesti |
| EP1812008A4 (fr) * | 2004-10-20 | 2008-10-29 | Smithkline Beecham Corp | Antagonistes du récepteur il-8 |
| CN101495113A (zh) * | 2006-04-21 | 2009-07-29 | 史密丝克莱恩比彻姆公司 | Il-8受体拮抗剂 |
| MY145810A (en) * | 2006-04-21 | 2012-04-30 | Smithkline Beecham Corp | Il-8 receptor antagonists |
| US7671058B2 (en) | 2006-06-21 | 2010-03-02 | Institute Of Medicinal Molecular Design, Inc. | N-(3,4-disubstituted phenyl) salicylamide derivatives |
| AR061571A1 (es) * | 2006-06-23 | 2008-09-03 | Smithkline Beecham Corp | Compuesto sal del acido toluenosulfonico de 4-{[6-cloro-3-({[(2- cloro-3-fluorofenil) amino]carbonil} amino)- 2- hidroxifenil]sulfonil] -1- piperazinacarbxilato de 1.1-dimetiletilo, composicion farmaceutica que lo comprende su uso para la fabricacion de un medicamento combinacion farmaceutica con un |
| EP2110019A1 (fr) | 2008-04-19 | 2009-10-21 | Bayer CropScience AG | Composés herbicides à base de N-azinyl-N'-pyridylsulfonylurées |
| JP6067226B2 (ja) | 2009-03-13 | 2017-01-25 | アジオス ファーマシューティカルズ, インコーポレイテッド | 細胞増殖関連疾患のための方法および組成物 |
| CR20170071A (es) | 2009-06-29 | 2017-03-28 | Agios Pharmaceuticals Inc | Compuestos terapeuticos y composiciones |
| JP2013508318A (ja) * | 2009-10-21 | 2013-03-07 | バイエル・ファルマ・アクチェンゲゼルシャフト | 置換されたベンゾスルホンアミド誘導体 |
| CA2793836C (fr) | 2009-10-21 | 2020-03-24 | Agios Pharmaceuticals, Inc. | Procedes et compositions pour troubles associes a la proliferation cellulaire |
| WO2011050210A1 (fr) | 2009-10-21 | 2011-04-28 | Agios Pharmaceuticals, Inc. | Procedes et compositions pour des troubles relatifs |
| JP2013514313A (ja) | 2009-12-17 | 2013-04-25 | ガルデルマ・リサーチ・アンド・デヴェロップメント | 皮膚障害の治療又は予防における化合物の使用 |
| ME03074B (fr) | 2011-05-03 | 2019-01-20 | Agios Pharmaceuticals Inc | Activateurs de la pyruvate kinase destinés à être utilisés en thérapie |
| CN102827170A (zh) | 2011-06-17 | 2012-12-19 | 安吉奥斯医药品有限公司 | 治疗活性组合物和它们的使用方法 |
| CN102827073A (zh) | 2011-06-17 | 2012-12-19 | 安吉奥斯医药品有限公司 | 治疗活性组合物和它们的使用方法 |
| KR101893112B1 (ko) | 2012-01-06 | 2018-08-30 | 아지오스 파마슈티컬스 아이엔씨. | 치료학적으로 활성인 화합물 및 이의 이용 방법 |
| US9474779B2 (en) | 2012-01-19 | 2016-10-25 | Agios Pharmaceuticals, Inc. | Therapeutically active compositions and their methods of use |
| WO2014062511A1 (fr) * | 2012-10-15 | 2014-04-24 | Agios Pharmaceuticals, Inc. | Composés et compositions thérapeutiques |
| US9579324B2 (en) | 2013-07-11 | 2017-02-28 | Agios Pharmaceuticals, Inc | Therapeutically active compounds and their methods of use |
| CA2917671A1 (fr) | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Composes de 2,4 ou de 4,6-diaminopyrimidine en tant qu'inhibiteurs des mutants idh2 pour le traitement du cancer |
| WO2015003355A2 (fr) | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Composés thérapeutiquement actifs et leurs méthodes d'utilisation |
| WO2015003360A2 (fr) | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Composés thérapeutiquement actifs et leurs méthodes d'utilisation |
| PE20160744A1 (es) | 2013-07-11 | 2016-08-01 | Agios Pharmaceuticals Inc | Compuestos de n,6-bis(aril o heteroaril)-1,3,5-triazin-2,4-diamina como inhibidores de idh2 mutantes para el tratamiento de cancer |
| US20150031627A1 (en) | 2013-07-25 | 2015-01-29 | Agios Pharmaceuticals, Inc | Therapeutically active compounds and their methods of use |
| PH12021551647A1 (en) | 2014-03-14 | 2022-06-06 | Agios Pharmaceuticals Inc | Pharmaceutical compositions of therapeutically active compounds |
| FR3030515B1 (fr) | 2014-12-23 | 2017-01-20 | Galderma Res & Dev | Nouveaux composes antagonistes des recepteurs cxcr1 et cxcr2 aux chimiokines, et leur utilisation dans le traitement de pathologies mediees par des chimiokines |
| MA44392B1 (fr) | 2015-06-11 | 2023-10-31 | Agios Pharmaceuticals Inc | Procédés d'utilisation d'activateurs de la pyruvate kinase |
| ES2897959T3 (es) | 2015-10-15 | 2022-03-03 | Servier Lab | Terapia de combinación para tratar neoplasias malignas |
| KR20250126877A (ko) | 2015-10-15 | 2025-08-25 | 르 라보레또레 쎄르비에르 | 악성 종양의 치료를 위한 조합물 요법 |
| US10980788B2 (en) | 2018-06-08 | 2021-04-20 | Agios Pharmaceuticals, Inc. | Therapy for treating malignancies |
| CN112778167A (zh) * | 2019-11-01 | 2021-05-11 | 邵阳学院 | 一种快速制备n-苯磺酰基氨基酸酯类化合物的方法 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3972886A (en) * | 1972-07-13 | 1976-08-03 | Leo Pharmaceutical Products Ltd. | Certain 4-phenoxy-3-heteroarylmethyl or ethyl sulfamyl benzoic acid derivatives |
| US4155930A (en) * | 1978-07-11 | 1979-05-22 | American Cyanamid Company | Ureylene phenylene anionic naphthalenesulfonic acids |
| US4786316A (en) * | 1984-07-13 | 1988-11-22 | E. I. Du Pont De Nemours And Company | Herbicidal ortho-sulfamoyl sulfonamides |
| KR20000022273A (ko) * | 1996-06-27 | 2000-04-25 | 스튜어트 알. 수터, 스티븐 베네티아너, 피터 존 기딩스 | Il-8 수용체 길항제 |
| JP2000513360A (ja) * | 1996-06-27 | 2000-10-10 | 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 |
| DE69826695T2 (de) * | 1997-05-23 | 2006-02-02 | Bayer Pharmaceuticals Corp., West Haven | Arylharnstoffderivate zur behandlung von inflammatorischen oder immunomodulatorischen erkrankungen |
-
1999
- 1999-12-09 UY UY25842A patent/UY25842A1/es unknown
- 1999-12-12 DZ DZ990264A patent/DZ2964A1/fr active
- 1999-12-13 CO CO99077673A patent/CO4990929A1/es unknown
- 1999-12-14 PE PE1999001243A patent/PE20001323A1/es not_active Application Discontinuation
- 1999-12-14 AR ARP990106373A patent/AR029605A1/es not_active Application Discontinuation
- 1999-12-15 DE DE1999615888 patent/DE69915888T2/de not_active Expired - Lifetime
- 1999-12-15 TR TR2001/01772T patent/TR200101772T2/xx unknown
- 1999-12-15 WO PCT/US1999/029940 patent/WO2000035442A1/fr not_active Ceased
- 1999-12-15 AT AT99965288T patent/ATE262328T1/de active
- 1999-12-15 BR BR9916159-1A patent/BR9916159A/pt not_active IP Right Cessation
- 1999-12-15 CA CA002355890A patent/CA2355890A1/fr not_active Abandoned
- 1999-12-15 IL IL14350799A patent/IL143507A0/xx unknown
- 1999-12-15 PL PL99348179A patent/PL348179A1/xx not_active Application Discontinuation
- 1999-12-15 KR KR1020017007504A patent/KR20010101243A/ko not_active Ceased
- 1999-12-15 NZ NZ511993A patent/NZ511993A/en not_active IP Right Cessation
- 1999-12-15 DK DK99965288T patent/DK1161232T3/da active
- 1999-12-15 EA EA200100659A patent/EA005210B1/ru not_active IP Right Cessation
- 1999-12-15 EP EP99965288A patent/EP1161232B1/fr not_active Expired - Lifetime
- 1999-12-15 AU AU31237/00A patent/AU748799B2/en not_active Ceased
- 1999-12-15 OA OA1200100154A patent/OA11731A/en unknown
- 1999-12-15 JP JP2000587762A patent/JP2002532419A/ja not_active Ceased
- 1999-12-15 CZ CZ20012150A patent/CZ20012150A3/cs unknown
- 1999-12-15 PT PT99965288T patent/PT1161232E/pt unknown
- 1999-12-15 US US09/868,165 patent/US6500863B1/en not_active Expired - Fee Related
- 1999-12-15 CN CN99816125A patent/CN1334726A/zh active Pending
- 1999-12-15 HK HK02103608.6A patent/HK1043535B/en not_active IP Right Cessation
- 1999-12-15 SK SK822-2001A patent/SK8222001A3/sk unknown
- 1999-12-15 ES ES99965288T patent/ES2217871T3/es not_active Expired - Lifetime
- 1999-12-15 HU HU0104686A patent/HUP0104686A3/hu unknown
-
2001
- 2001-06-13 MA MA26236A patent/MA25366A1/fr unknown
- 2001-06-14 NO NO20012948A patent/NO20012948L/no not_active Application Discontinuation
- 2001-06-29 BG BG105661A patent/BG105661A/xx unknown
-
2002
- 2002-11-18 US US10/299,503 patent/US20030109527A1/en not_active Abandoned
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