JP2001526276A5 - - Google Patents
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- Publication number
- JP2001526276A5 JP2001526276A5 JP2000525400A JP2000525400A JP2001526276A5 JP 2001526276 A5 JP2001526276 A5 JP 2001526276A5 JP 2000525400 A JP2000525400 A JP 2000525400A JP 2000525400 A JP2000525400 A JP 2000525400A JP 2001526276 A5 JP2001526276 A5 JP 2001526276A5
- Authority
- JP
- Japan
- Prior art keywords
- urea
- halogen
- substituted
- alkyl
- methoxyphenyl
- 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.)
- Granted
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- 229910052736 halogen Inorganic materials 0.000 description 50
- 125000000217 alkyl group Chemical group 0.000 description 45
- 125000003545 alkoxy group Chemical group 0.000 description 33
- 150000002367 halogens Chemical class 0.000 description 31
- 125000005843 halogen group Chemical group 0.000 description 24
- 229910052799 carbon Inorganic materials 0.000 description 20
- 229910052739 hydrogen Inorganic materials 0.000 description 18
- 125000003118 aryl group Chemical group 0.000 description 17
- 125000001072 heteroaryl group Chemical group 0.000 description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
- 239000003814 drug Substances 0.000 description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 10
- -1 methyl-substituted pyrrole Chemical class 0.000 description 10
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 7
- 125000002877 alkyl aryl group Chemical group 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 125000005213 alkyl heteroaryl group Chemical group 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 239000004202 carbamide Substances 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical group C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical group N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 125000001589 carboacyl group Chemical group 0.000 description 4
- 125000004076 pyridyl group Chemical group 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 3
- NQSGLPJENUWZCH-UHFFFAOYSA-N 2-[4-tert-butyl-2-[(2,3-dichlorophenyl)carbamoylamino]phenoxy]-n-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC1=CC=CC(Cl)=C1Cl NQSGLPJENUWZCH-UHFFFAOYSA-N 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 230000001404 mediated effect Effects 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- HIXNPJUOIABYJB-UHFFFAOYSA-N 1-(3-chloro-4-fluorophenyl)-3-[5-(difluoromethylsulfonyl)-2-methoxyphenyl]urea Chemical compound COC1=CC=C(S(=O)(=O)C(F)F)C=C1NC(=O)NC1=CC=C(F)C(Cl)=C1 HIXNPJUOIABYJB-UHFFFAOYSA-N 0.000 description 2
- BVGDTMAZIBUCJX-UHFFFAOYSA-N 1-(3-chloro-4-methylphenyl)-3-[5-(difluoromethylsulfonyl)-2-methoxyphenyl]urea Chemical compound COC1=CC=C(S(=O)(=O)C(F)F)C=C1NC(=O)NC1=CC=C(C)C(Cl)=C1 BVGDTMAZIBUCJX-UHFFFAOYSA-N 0.000 description 2
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 description 2
- FUOBTFFYDOUWJF-UHFFFAOYSA-N 1-[5-(difluoromethylsulfonyl)-2-methoxyphenyl]-3-(2,3-dimethylphenyl)urea Chemical compound COC1=CC=C(S(=O)(=O)C(F)F)C=C1NC(=O)NC1=CC=CC(C)=C1C FUOBTFFYDOUWJF-UHFFFAOYSA-N 0.000 description 2
- NSCICEWWQXGDBG-UHFFFAOYSA-N 1-[5-(difluoromethylsulfonyl)-2-methoxyphenyl]-3-(2-fluoro-4-methylphenyl)urea Chemical compound COC1=CC=C(S(=O)(=O)C(F)F)C=C1NC(=O)NC1=CC=C(C)C=C1F NSCICEWWQXGDBG-UHFFFAOYSA-N 0.000 description 2
- ORPATFVSFMGXEK-UHFFFAOYSA-N 1-[5-(difluoromethylsulfonyl)-2-methoxyphenyl]-3-(3-fluoro-4-methylphenyl)urea Chemical compound COC1=CC=C(S(=O)(=O)C(F)F)C=C1NC(=O)NC1=CC=C(C)C(F)=C1 ORPATFVSFMGXEK-UHFFFAOYSA-N 0.000 description 2
- FLQZHESNDLWZGI-UHFFFAOYSA-N 1-[5-(difluoromethylsulfonyl)-2-methoxyphenyl]-3-(4-fluoro-3-methylphenyl)urea Chemical compound COC1=CC=C(S(=O)(=O)C(F)F)C=C1NC(=O)NC1=CC=C(F)C(C)=C1 FLQZHESNDLWZGI-UHFFFAOYSA-N 0.000 description 2
- IQTQAOVHKVVSRJ-UHFFFAOYSA-N 1-[5-(difluoromethylsulfonyl)-2-methoxyphenyl]-3-(4-fluorophenyl)urea Chemical compound COC1=CC=C(S(=O)(=O)C(F)F)C=C1NC(=O)NC1=CC=C(F)C=C1 IQTQAOVHKVVSRJ-UHFFFAOYSA-N 0.000 description 2
- JNGWTTDGSWDQFT-UHFFFAOYSA-N 1-[5-(difluoromethylsulfonyl)-2-methoxyphenyl]-3-(4-methylphenyl)urea Chemical compound COC1=CC=C(S(=O)(=O)C(F)F)C=C1NC(=O)NC1=CC=C(C)C=C1 JNGWTTDGSWDQFT-UHFFFAOYSA-N 0.000 description 2
- AUWOOQSOMNALEH-UHFFFAOYSA-N 1-[5-tert-butyl-2-(oxolan-3-yloxy)phenyl]-3-(2,3-dichlorophenyl)urea Chemical compound C=1C=CC(Cl)=C(Cl)C=1NC(=O)NC1=CC(C(C)(C)C)=CC=C1OC1CCOC1 AUWOOQSOMNALEH-UHFFFAOYSA-N 0.000 description 2
- ZFXKBQLAXHAGGU-UHFFFAOYSA-N 2-[4-tert-butyl-2-(naphthalen-1-ylcarbamoylamino)phenoxy]-n-methylacetamide Chemical compound CNC(=O)COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC1=CC=CC2=CC=CC=C12 ZFXKBQLAXHAGGU-UHFFFAOYSA-N 0.000 description 2
- XSAJLMSHKDARQZ-UHFFFAOYSA-N C1[N-]CCOC1 Chemical compound C1[N-]CCOC1 XSAJLMSHKDARQZ-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Chemical group C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical group C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical group O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- LYKMMUBOEFYJQG-UHFFFAOYSA-N piperoxan Chemical group C1OC2=CC=CC=C2OC1CN1CCCCC1 LYKMMUBOEFYJQG-UHFFFAOYSA-N 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- CIMJBQAYBPMLBL-UHFFFAOYSA-N 1-(2,3-dimethylphenyl)-3-(3-methoxynaphthalen-2-yl)urea Chemical compound COC1=CC2=CC=CC=C2C=C1NC(=O)NC1=CC=CC(C)=C1C CIMJBQAYBPMLBL-UHFFFAOYSA-N 0.000 description 1
- FWYLZUATYISQMP-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-3-[2-methoxy-5-(trifluoromethyl)phenyl]urea Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)NC1=CC=C(F)C=C1F FWYLZUATYISQMP-UHFFFAOYSA-N 0.000 description 1
- SUCUGGJVKQQPES-UHFFFAOYSA-N 1-(2-fluoro-4-methylphenyl)-3-[2-methoxy-5-(trifluoromethyl)phenyl]urea Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)NC1=CC=C(C)C=C1F SUCUGGJVKQQPES-UHFFFAOYSA-N 0.000 description 1
- KUGJJKWDMFQOSJ-UHFFFAOYSA-N 1-(2-fluorophenyl)-3-(3-methoxynaphthalen-2-yl)urea Chemical compound COC1=CC2=CC=CC=C2C=C1NC(=O)NC1=CC=CC=C1F KUGJJKWDMFQOSJ-UHFFFAOYSA-N 0.000 description 1
- DWJLOSAVQXZQEK-UHFFFAOYSA-N 1-(3,5-dichloro-4-phenoxyphenyl)-3-[2-methoxy-5-(trifluoromethyl)phenyl]urea Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)NC(C=C1Cl)=CC(Cl)=C1OC1=CC=CC=C1 DWJLOSAVQXZQEK-UHFFFAOYSA-N 0.000 description 1
- SUEHBAZECVRTOQ-UHFFFAOYSA-N 1-(3-chloro-4-fluorophenyl)-3-[2-methoxy-5-(trifluoromethyl)phenyl]urea Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)NC1=CC=C(F)C(Cl)=C1 SUEHBAZECVRTOQ-UHFFFAOYSA-N 0.000 description 1
- ONUBJNPWBUNSDO-UHFFFAOYSA-N 1-(3-chloro-4-methylphenyl)-3-[2-methoxy-5-(trifluoromethyl)phenyl]urea Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)NC1=CC=C(C)C(Cl)=C1 ONUBJNPWBUNSDO-UHFFFAOYSA-N 0.000 description 1
- RVRRXOGHQFPGEO-UHFFFAOYSA-N 1-(3-fluoro-4-methylphenyl)-3-(3-methoxynaphthalen-2-yl)urea Chemical compound COC1=CC2=CC=CC=C2C=C1NC(=O)NC1=CC=C(C)C(F)=C1 RVRRXOGHQFPGEO-UHFFFAOYSA-N 0.000 description 1
- NACDJICRDYELIJ-UHFFFAOYSA-N 1-(3-fluoro-4-methylphenyl)-3-[2-methoxy-5-(trifluoromethyl)phenyl]urea Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)NC1=CC=C(C)C(F)=C1 NACDJICRDYELIJ-UHFFFAOYSA-N 0.000 description 1
- CPXWLAHCVVXGEX-UHFFFAOYSA-N 1-(3-fluorophenyl)-3-(3-methoxynaphthalen-2-yl)urea Chemical compound COC1=CC2=CC=CC=C2C=C1NC(=O)NC1=CC=CC(F)=C1 CPXWLAHCVVXGEX-UHFFFAOYSA-N 0.000 description 1
- NARZIXFXYQEUCF-UHFFFAOYSA-N 1-(3-methoxynaphthalen-2-yl)-3-(4-methylphenyl)urea Chemical compound COC1=CC2=CC=CC=C2C=C1NC(=O)NC1=CC=C(C)C=C1 NARZIXFXYQEUCF-UHFFFAOYSA-N 0.000 description 1
- IDWWOMPHWKJLGC-UHFFFAOYSA-N 1-(3-methoxynaphthalen-2-yl)-3-(4-pyridin-4-ylsulfanylphenyl)urea Chemical compound COC1=CC2=CC=CC=C2C=C1NC(=O)NC(C=C1)=CC=C1SC1=CC=NC=C1 IDWWOMPHWKJLGC-UHFFFAOYSA-N 0.000 description 1
- UBZGBQRSXPGADO-UHFFFAOYSA-N 1-(3-methoxynaphthalen-2-yl)-3-[4-(pyridin-4-ylmethyl)phenyl]urea Chemical compound COC1=CC2=CC=CC=C2C=C1NC(=O)NC(C=C1)=CC=C1CC1=CC=NC=C1 UBZGBQRSXPGADO-UHFFFAOYSA-N 0.000 description 1
- RGBHNZLHKCUWSG-UHFFFAOYSA-N 1-(3-methoxynaphthalen-2-yl)-3-naphthalen-1-ylurea Chemical compound C1=CC=C2C(NC(=O)NC3=CC4=CC=CC=C4C=C3OC)=CC=CC2=C1 RGBHNZLHKCUWSG-UHFFFAOYSA-N 0.000 description 1
- JVVLHNHJGIXXCQ-UHFFFAOYSA-N 1-(5-chloro-2-hydroxy-4-nitrophenyl)-3-[4-(pyridin-4-ylmethyl)phenyl]urea Chemical compound OC1=CC([N+]([O-])=O)=C(Cl)C=C1NC(=O)NC(C=C1)=CC=C1CC1=CC=NC=C1 JVVLHNHJGIXXCQ-UHFFFAOYSA-N 0.000 description 1
- ASMCVDDUQQZBFK-UHFFFAOYSA-N 1-(5-chloro-2-hydroxy-4-nitrophenyl)-3-phenylurea Chemical compound OC1=CC([N+]([O-])=O)=C(Cl)C=C1NC(=O)NC1=CC=CC=C1 ASMCVDDUQQZBFK-UHFFFAOYSA-N 0.000 description 1
- AWNQQYAADTXMNT-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-(4-phenoxyphenyl)urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=CC=C1 AWNQQYAADTXMNT-UHFFFAOYSA-N 0.000 description 1
- KSJWFOMLEIROON-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 KSJWFOMLEIROON-UHFFFAOYSA-N 0.000 description 1
- UIIMLVRGKRPKJF-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-(4-pyridin-4-ylsulfanylphenyl)urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1SC1=CC=NC=C1 UIIMLVRGKRPKJF-UHFFFAOYSA-N 0.000 description 1
- OCPGRDMOAPCBAN-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(4-methoxyphenoxy)phenyl]urea Chemical compound C1=CC(OC)=CC=C1OC(C=C1)=CC=C1NC(=O)NC1=CC(C(C)(C)C)=CC=C1OC OCPGRDMOAPCBAN-UHFFFAOYSA-N 0.000 description 1
- BQUTVXTUZCAKSG-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(pyridin-3-ylmethyl)phenyl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1CC1=CC=CN=C1 BQUTVXTUZCAKSG-UHFFFAOYSA-N 0.000 description 1
- XNIGDEIZAANVJQ-UHFFFAOYSA-N 1-(5-tert-butyl-2-methoxyphenyl)-3-[4-(pyridin-4-ylmethyl)phenyl]urea Chemical compound COC1=CC=C(C(C)(C)C)C=C1NC(=O)NC(C=C1)=CC=C1CC1=CC=NC=C1 XNIGDEIZAANVJQ-UHFFFAOYSA-N 0.000 description 1
- ANGVHJHUUCSQAW-UHFFFAOYSA-N 1-(5-tert-butyl-2-phenylphenyl)-3-(2,3-dichlorophenyl)urea Chemical compound C=1C(C(C)(C)C)=CC=C(C=2C=CC=CC=2)C=1NC(=O)NC1=CC=CC(Cl)=C1Cl ANGVHJHUUCSQAW-UHFFFAOYSA-N 0.000 description 1
- YRHGPXLYOAFTRO-UHFFFAOYSA-N 1-(5-tert-butyl-2-thiophen-3-ylphenyl)-3-(2,3-dichlorophenyl)urea Chemical compound C=1C=CC(Cl)=C(Cl)C=1NC(=O)NC1=CC(C(C)(C)C)=CC=C1C=1C=CSC=1 YRHGPXLYOAFTRO-UHFFFAOYSA-N 0.000 description 1
- QXEQXIYKHSLSID-UHFFFAOYSA-N 1-[2-methoxy-5-(trifluoromethyl)phenyl]-3-(3-pyridin-4-ylsulfanylphenyl)urea Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)NC1=CC=CC(SC=2C=CN=CC=2)=C1 QXEQXIYKHSLSID-UHFFFAOYSA-N 0.000 description 1
- XQXIPVQCMSNTRN-UHFFFAOYSA-N 1-[2-methoxy-5-(trifluoromethyl)phenyl]-3-(4-methylphenyl)urea Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)NC1=CC=C(C)C=C1 XQXIPVQCMSNTRN-UHFFFAOYSA-N 0.000 description 1
- MWSOHEJRUMZBJC-UHFFFAOYSA-N 1-[2-methoxy-5-(trifluoromethyl)phenyl]-3-(4-pyridin-4-yloxyphenyl)urea Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)NC(C=C1)=CC=C1OC1=CC=NC=C1 MWSOHEJRUMZBJC-UHFFFAOYSA-N 0.000 description 1
- XSIGIAGUVJSXBS-UHFFFAOYSA-N 1-[2-methoxy-5-(trifluoromethyl)phenyl]-3-(4-pyridin-4-ylsulfanylphenyl)urea Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)NC(C=C1)=CC=C1SC1=CC=NC=C1 XSIGIAGUVJSXBS-UHFFFAOYSA-N 0.000 description 1
- QDWXEIYYKTWRNF-UHFFFAOYSA-N 1-[2-methoxy-5-(trifluoromethyl)phenyl]-3-[4-(pyridin-4-ylmethyl)phenyl]urea Chemical compound COC1=CC=C(C(F)(F)F)C=C1NC(=O)NC(C=C1)=CC=C1CC1=CC=NC=C1 QDWXEIYYKTWRNF-UHFFFAOYSA-N 0.000 description 1
- WYOKSNOAQIXIOE-UHFFFAOYSA-N 1-[2-methoxy-5-(trifluoromethylsulfonyl)phenyl]-3-(4-methylphenyl)urea Chemical compound COC1=CC=C(S(=O)(=O)C(F)(F)F)C=C1NC(=O)NC1=CC=C(C)C=C1 WYOKSNOAQIXIOE-UHFFFAOYSA-N 0.000 description 1
- VKUYLANQOAKALN-UHFFFAOYSA-N 2-[benzyl-(4-methoxyphenyl)sulfonylamino]-n-hydroxy-4-methylpentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(CC(C)C)C(=O)NO)CC1=CC=CC=C1 VKUYLANQOAKALN-UHFFFAOYSA-N 0.000 description 1
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 1
- KYEACNNYFNZCST-UHFFFAOYSA-N CN(C(CC1)=O)C1=O Chemical compound CN(C(CC1)=O)C1=O KYEACNNYFNZCST-UHFFFAOYSA-N 0.000 description 1
- NXUBPJOMIBZQST-UHFFFAOYSA-N CN(C1OC1CC1)C1=O Chemical compound CN(C1OC1CC1)C1=O NXUBPJOMIBZQST-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N CN(CCC1)C1=O Chemical compound CN(CCC1)C1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- JTPZTKBRUCILQD-UHFFFAOYSA-N CN(CCN1)C1=O Chemical compound CN(CCN1)C1=O JTPZTKBRUCILQD-UHFFFAOYSA-N 0.000 description 1
- KIRCYRMNYHUMHH-UHFFFAOYSA-N COC1=C(C=C(C=C1)S(=O)(=O)C(F)F)NC(=O)N Chemical compound COC1=C(C=C(C=C1)S(=O)(=O)C(F)F)NC(=O)N KIRCYRMNYHUMHH-UHFFFAOYSA-N 0.000 description 1
- BOCZJMMVTZKBGE-UHFFFAOYSA-N COC1=CC=C(S(F)(=O)=O)C=C1NC(=O)NC1=CC=C(C)C=C1 Chemical compound COC1=CC=C(S(F)(=O)=O)C=C1NC(=O)NC1=CC=C(C)C=C1 BOCZJMMVTZKBGE-UHFFFAOYSA-N 0.000 description 1
- 241000252095 Congridae Species 0.000 description 1
- 108090000695 Cytokines Proteins 0.000 description 1
- 102000004127 Cytokines Human genes 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 108010002352 Interleukin-1 Proteins 0.000 description 1
- 102000000589 Interleukin-1 Human genes 0.000 description 1
- 108090001005 Interleukin-6 Proteins 0.000 description 1
- 102000004889 Interleukin-6 Human genes 0.000 description 1
- 108090001007 Interleukin-8 Proteins 0.000 description 1
- 102000004890 Interleukin-8 Human genes 0.000 description 1
- 102000000380 Matrix Metalloproteinase 1 Human genes 0.000 description 1
- 108010016113 Matrix Metalloproteinase 1 Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- 102100030416 Stromelysin-1 Human genes 0.000 description 1
- 101710108790 Stromelysin-1 Proteins 0.000 description 1
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 1
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US99574997A | 1997-12-22 | 1997-12-22 | |
| US08/995,749 | 1997-12-22 | ||
| PCT/US1998/027265 WO1999032463A1 (en) | 1997-12-22 | 1998-12-22 | INHIBITION OF p38 KINASE USING SYMMETRICAL AND UNSYMMETRICAL DIPHENYL UREAS |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001526276A JP2001526276A (ja) | 2001-12-18 |
| JP2001526276A5 true JP2001526276A5 (https=) | 2006-01-05 |
| JP3887769B2 JP3887769B2 (ja) | 2007-02-28 |
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| JP2000525400A Expired - Fee Related JP3887769B2 (ja) | 1997-12-22 | 1998-12-22 | 対称および非対称ジフェニル尿素を用いるｐ３８キナーゼの阻害 |
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| JP (1) | JP3887769B2 (https=) |
| AT (1) | ATE297383T1 (https=) |
| AU (1) | AU1939999A (https=) |
| CA (1) | CA2315715C (https=) |
| DE (2) | DE1042305T1 (https=) |
| DK (1) | DK1042305T3 (https=) |
| ES (1) | ES2154252T3 (https=) |
| IL (3) | IL136737A0 (https=) |
| PT (1) | PT1042305E (https=) |
| WO (1) | WO1999032463A1 (https=) |
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| JP6510485B2 (ja) | 2013-03-15 | 2019-05-08 | オハイオ・ステイト・イノベーション・ファウンデーション | Ｐｒｍｔ５インヒビターおよびそれらの使用方法 |
| WO2015003360A2 (en) | 2013-07-11 | 2015-01-15 | Agios Pharmaceuticals, Inc. | Therapeutically active compounds and their methods of use |
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| US9638690B2 (en) | 2014-11-07 | 2017-05-02 | The University Of British Columbia | Compounds and compositions for use as alkylating agent sensors and methods of use thereof |
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| US11053255B2 (en) | 2015-06-22 | 2021-07-06 | Georgetown University | Synthesis of mahanine and related compounds |
| WO2017011767A2 (en) | 2015-07-15 | 2017-01-19 | Axovant Sciences Ltd. | Diaryl and arylheteroaryl urea derivatives as modulators of the 5-ht2a serotonin receptor useful for the prophylaxis and treatment of hallucinations associated with a neurodegenerative disease |
| PT3362066T (pt) | 2015-10-15 | 2021-11-16 | Celgene Corp | Terapia de combinação para tratar malignidades |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB828231A (en) * | 1955-10-20 | 1960-02-17 | Geigy Ag J R | Improvements relating to insecticidal compounds and their use |
| NL254871A (https=) * | 1959-08-14 | |||
| NL277511A (https=) * | 1961-04-21 | |||
| US3200035A (en) * | 1962-06-01 | 1965-08-10 | Ciba Ltd | Treatment of synthetic products, especially synthetic fibers |
| DE2928485A1 (de) * | 1979-07-14 | 1981-01-29 | Bayer Ag | Verwendung von harnstoffderivaten als arzneimittel bei der behandlung von fettstoffwechselstoerungen |
| WO1998052558A1 (en) * | 1997-05-23 | 1998-11-26 | Bayer Corporation | INHIBITION OF p38 KINASE ACTIVITY BY ARYL UREAS |
-
1998
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- 1998-12-22 AT AT98964221T patent/ATE297383T1/de active
- 1998-12-22 DK DK98964221T patent/DK1042305T3/da active
- 1998-12-22 DE DE1042305T patent/DE1042305T1/de active Pending
- 1998-12-22 WO PCT/US1998/027265 patent/WO1999032463A1/en not_active Ceased
- 1998-12-22 AU AU19399/99A patent/AU1939999A/en not_active Abandoned
- 1998-12-22 ES ES98964221T patent/ES2154252T3/es not_active Expired - Lifetime
- 1998-12-22 DE DE69830513T patent/DE69830513T2/de not_active Expired - Lifetime
- 1998-12-22 EP EP98964221A patent/EP1042305B1/en not_active Expired - Lifetime
- 1998-12-22 CA CA2315715A patent/CA2315715C/en not_active Expired - Lifetime
- 1998-12-22 EP EP05012144A patent/EP1616865A1/en not_active Ceased
- 1998-12-22 IL IL13673798A patent/IL136737A0/xx active IP Right Grant
- 1998-12-22 PT PT98964221T patent/PT1042305E/pt unknown
-
2000
- 2000-06-13 IL IL136737A patent/IL136737A/en not_active IP Right Cessation
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2005
- 2005-08-11 IL IL170235A patent/IL170235A/en not_active IP Right Cessation
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