NO315786B1 - Inhibisjon av leukotrienbiosyntese med ureaderivater - Google Patents
Inhibisjon av leukotrienbiosyntese med ureaderivater Download PDFInfo
- Publication number
- NO315786B1 NO315786B1 NO19970477A NO970477A NO315786B1 NO 315786 B1 NO315786 B1 NO 315786B1 NO 19970477 A NO19970477 A NO 19970477A NO 970477 A NO970477 A NO 970477A NO 315786 B1 NO315786 B1 NO 315786B1
- Authority
- NO
- Norway
- Prior art keywords
- hydroxy
- urea
- phenyl
- carbon atoms
- phenylurea
- Prior art date
Links
- 150000002617 leukotrienes Chemical class 0.000 title claims abstract description 21
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 17
- 230000005764 inhibitory process Effects 0.000 title claims description 23
- 150000003672 ureas Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 97
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 59
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- -1 3-(4-butylphenyl)-1-hydroxy-1 - phenylurea Chemical compound 0.000 claims description 40
- 239000004202 carbamide Substances 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 150000001768 cations Chemical class 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- JGSIAOZAXBWRFO-UHFFFAOYSA-N 3-methylsulfanyl-1-phenyl-4,5-dihydrobenzo[g]indazole Chemical compound C1CC2=CC=CC=C2C2=C1C(SC)=NN2C1=CC=CC=C1 JGSIAOZAXBWRFO-UHFFFAOYSA-N 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 238000001727 in vivo Methods 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-UHFFFAOYSA-N 0.000 claims description 4
- XUPPUXBZXIIYGF-UHFFFAOYSA-N 1-butan-2-yl-1-hydroxy-3-phenylurea Chemical compound CCC(C)N(O)C(=O)NC1=CC=CC=C1 XUPPUXBZXIIYGF-UHFFFAOYSA-N 0.000 claims description 4
- VHDKOUQVFHQSLW-UHFFFAOYSA-N 1-heptan-4-yl-1-hydroxy-3-phenylurea Chemical compound CCCC(CCC)N(O)C(=O)NC1=CC=CC=C1 VHDKOUQVFHQSLW-UHFFFAOYSA-N 0.000 claims description 4
- FTHPVFHMPAFSEK-UHFFFAOYSA-N 1-hydroxy-1-methyl-3-(4-phenoxyphenyl)urea Chemical compound C1=CC(NC(=O)N(O)C)=CC=C1OC1=CC=CC=C1 FTHPVFHMPAFSEK-UHFFFAOYSA-N 0.000 claims description 4
- DNKZRQIPYKONDX-UHFFFAOYSA-N 1-hydroxy-1-pentan-3-yl-3-(2-phenoxyphenyl)urea Chemical compound CCC(CC)N(O)C(=O)NC1=CC=CC=C1OC1=CC=CC=C1 DNKZRQIPYKONDX-UHFFFAOYSA-N 0.000 claims description 4
- VECSJEDODMVSJD-UHFFFAOYSA-N 1-hydroxy-1-pentan-3-yl-3-(3-phenoxyphenyl)urea Chemical compound CCC(CC)N(O)C(=O)NC1=CC=CC(OC=2C=CC=CC=2)=C1 VECSJEDODMVSJD-UHFFFAOYSA-N 0.000 claims description 4
- ZIGHLRAVHFVRLS-UHFFFAOYSA-N 1-hydroxy-1-pentan-3-yl-3-(4-phenoxyphenyl)urea Chemical compound C1=CC(NC(=O)N(O)C(CC)CC)=CC=C1OC1=CC=CC=C1 ZIGHLRAVHFVRLS-UHFFFAOYSA-N 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 208000006673 asthma Diseases 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- CBMUGPKLGKEKPR-UHFFFAOYSA-N 1-cyclooctyl-1-hydroxy-3-(4-methoxyphenyl)urea Chemical compound C1=CC(OC)=CC=C1NC(=O)N(O)C1CCCCCCC1 CBMUGPKLGKEKPR-UHFFFAOYSA-N 0.000 claims description 3
- PZNYUIZWTWKNFN-UHFFFAOYSA-N 1-cyclooctyl-1-hydroxy-3-(4-nitrophenyl)urea Chemical compound C=1C=C([N+]([O-])=O)C=CC=1NC(=O)N(O)C1CCCCCCC1 PZNYUIZWTWKNFN-UHFFFAOYSA-N 0.000 claims description 3
- ZIXVMWVNEMPRGS-UHFFFAOYSA-N 1-cyclooctyl-1-hydroxy-3-phenylurea Chemical compound C=1C=CC=CC=1NC(=O)N(O)C1CCCCCCC1 ZIXVMWVNEMPRGS-UHFFFAOYSA-N 0.000 claims description 3
- DNWGFUVAFNEYNQ-UHFFFAOYSA-N 1-hexan-3-yl-1-hydroxy-3-phenylurea Chemical compound CCCC(CC)N(O)C(=O)NC1=CC=CC=C1 DNWGFUVAFNEYNQ-UHFFFAOYSA-N 0.000 claims description 3
- GSRXBOYHYVEDAZ-UHFFFAOYSA-N 1-hydroxy-1,3-dimethyl-3-phenylurea Chemical compound CN(O)C(=O)N(C)C1=CC=CC=C1 GSRXBOYHYVEDAZ-UHFFFAOYSA-N 0.000 claims description 3
- MIKNAGBXJJFBMH-UHFFFAOYSA-N 1-hydroxy-1-(2-methylpropyl)-3-phenylurea Chemical compound CC(C)CN(O)C(=O)NC1=CC=CC=C1 MIKNAGBXJJFBMH-UHFFFAOYSA-N 0.000 claims description 3
- KHRWQJXWOOYBPJ-UHFFFAOYSA-N 1-hydroxy-1-methyl-3-(4-methylsulfanylphenyl)urea Chemical compound CSC1=CC=C(NC(=O)N(C)O)C=C1 KHRWQJXWOOYBPJ-UHFFFAOYSA-N 0.000 claims description 3
- GHPVQGDLTYEKSE-UHFFFAOYSA-N 1-hydroxy-1-pentan-2-yl-3-phenylurea Chemical compound CCCC(C)N(O)C(=O)NC1=CC=CC=C1 GHPVQGDLTYEKSE-UHFFFAOYSA-N 0.000 claims description 3
- JLGFYLIGAKBPIM-UHFFFAOYSA-N 1-hydroxy-1-pentan-3-yl-3-(4-phenylphenyl)urea Chemical compound C1=CC(NC(=O)N(O)C(CC)CC)=CC=C1C1=CC=CC=C1 JLGFYLIGAKBPIM-UHFFFAOYSA-N 0.000 claims description 3
- YLBOOZRFNPXAAQ-UHFFFAOYSA-N 1-hydroxy-1-pentan-3-yl-3-phenylurea Chemical compound CCC(CC)N(O)C(=O)NC1=CC=CC=C1 YLBOOZRFNPXAAQ-UHFFFAOYSA-N 0.000 claims description 3
- VTRVQCIHWKQEBO-UHFFFAOYSA-N 3-(4-benzoylphenyl)-1-hydroxy-1-pentan-3-ylurea Chemical compound C1=CC(NC(=O)N(O)C(CC)CC)=CC=C1C(=O)C1=CC=CC=C1 VTRVQCIHWKQEBO-UHFFFAOYSA-N 0.000 claims description 3
- SSGRIYXOSFWTLN-UHFFFAOYSA-N 3-(4-butylphenyl)-1-hydroxy-1-propan-2-ylurea Chemical compound CCCCC1=CC=C(NC(=O)N(O)C(C)C)C=C1 SSGRIYXOSFWTLN-UHFFFAOYSA-N 0.000 claims description 3
- BAYJIVICNBMRFH-UHFFFAOYSA-N 3-[3,5-bis(trifluoromethyl)phenyl]-1-hydroxy-1-pentan-3-ylurea Chemical compound CCC(CC)N(O)C(=O)NC1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1 BAYJIVICNBMRFH-UHFFFAOYSA-N 0.000 claims description 3
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 3
- 201000005569 Gout Diseases 0.000 claims description 3
- 206010063837 Reperfusion injury Diseases 0.000 claims description 3
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 3
- 206010039085 Rhinitis allergic Diseases 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 3
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 3
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 3
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 3
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
- 201000010105 allergic rhinitis Diseases 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 230000000302 ischemic effect Effects 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 208000020431 spinal cord injury Diseases 0.000 claims description 3
- 230000009529 traumatic brain injury Effects 0.000 claims description 3
- GXENJOBLVCZEBW-UHFFFAOYSA-N 1-(2-ethoxyethyl)-1-hydroxy-3-phenylurea Chemical compound CCOCCN(O)C(=O)NC1=CC=CC=C1 GXENJOBLVCZEBW-UHFFFAOYSA-N 0.000 claims description 2
- SKCXCIJPVDTWDU-UHFFFAOYSA-N 1-(2-ethylhexyl)-1-hydroxy-3-phenylurea Chemical compound CCCCC(CC)CN(O)C(=O)NC1=CC=CC=C1 SKCXCIJPVDTWDU-UHFFFAOYSA-N 0.000 claims description 2
- XRKPPGJZSHRPRE-UHFFFAOYSA-N 1-cyclohexyl-1-hydroxy-3-(3-methylsulfanylphenyl)urea Chemical compound CSC1=CC=CC(NC(=O)N(O)C2CCCCC2)=C1 XRKPPGJZSHRPRE-UHFFFAOYSA-N 0.000 claims description 2
- PBKRZGRQYPZDOF-UHFFFAOYSA-N 1-cyclohexyl-1-hydroxy-3-(4-methylsulfanylphenyl)urea Chemical compound C1=CC(SC)=CC=C1NC(=O)N(O)C1CCCCC1 PBKRZGRQYPZDOF-UHFFFAOYSA-N 0.000 claims description 2
- IQMDJGZTJBEXBE-UHFFFAOYSA-N 1-ethyl-1-hydroxy-3-phenylurea Chemical compound CCN(O)C(=O)NC1=CC=CC=C1 IQMDJGZTJBEXBE-UHFFFAOYSA-N 0.000 claims description 2
- QEHHVWCTLFFYGB-UHFFFAOYSA-N 1-hydroxy-1-(2-methylpropyl)-3-(3-methylsulfanylphenyl)urea Chemical compound CSC1=CC=CC(NC(=O)N(O)CC(C)C)=C1 QEHHVWCTLFFYGB-UHFFFAOYSA-N 0.000 claims description 2
- DNDYVCLCRSOGAM-UHFFFAOYSA-N 1-hydroxy-1-methyl-3-(3-methylphenyl)urea Chemical compound CN(O)C(=O)NC1=CC=CC(C)=C1 DNDYVCLCRSOGAM-UHFFFAOYSA-N 0.000 claims description 2
- CDFBRZWZPFQLHK-UHFFFAOYSA-N 1-hydroxy-1-methyl-3-(3-methylsulfonylphenyl)urea Chemical compound CN(O)C(=O)NC1=CC=CC(S(C)(=O)=O)=C1 CDFBRZWZPFQLHK-UHFFFAOYSA-N 0.000 claims description 2
- SXQIEPLNJQLXPK-UHFFFAOYSA-N 1-hydroxy-1-methyl-3-(3-nitrophenyl)urea Chemical compound CN(O)C(=O)NC1=CC=CC([N+]([O-])=O)=C1 SXQIEPLNJQLXPK-UHFFFAOYSA-N 0.000 claims description 2
- QLCSFOCEFMIXJU-UHFFFAOYSA-N 1-hydroxy-1-methyl-3-(4-methylsulfinylphenyl)urea Chemical compound CN(O)C(=O)NC1=CC=C(S(C)=O)C=C1 QLCSFOCEFMIXJU-UHFFFAOYSA-N 0.000 claims description 2
- INWTVKADJULPBO-UHFFFAOYSA-N 1-hydroxy-1-methyl-3-(4-methylsulfonylphenyl)urea Chemical compound CN(O)C(=O)NC1=CC=C(S(C)(=O)=O)C=C1 INWTVKADJULPBO-UHFFFAOYSA-N 0.000 claims description 2
- QDWDPUOZHMWVAO-UHFFFAOYSA-N 1-hydroxy-1-methyl-3-(4-nitrophenyl)urea Chemical compound CN(O)C(=O)NC1=CC=C([N+]([O-])=O)C=C1 QDWDPUOZHMWVAO-UHFFFAOYSA-N 0.000 claims description 2
- WDFAHNFQLHAIAW-UHFFFAOYSA-N 1-hydroxy-1-methyl-3-phenylurea Chemical compound CN(O)C(=O)NC1=CC=CC=C1 WDFAHNFQLHAIAW-UHFFFAOYSA-N 0.000 claims description 2
- MBKLOKZYMMIOPI-UHFFFAOYSA-N 1-hydroxy-1-octyl-3-phenylurea Chemical compound CCCCCCCCN(O)C(=O)NC1=CC=CC=C1 MBKLOKZYMMIOPI-UHFFFAOYSA-N 0.000 claims description 2
- GBUJJTWYBQXKMP-UHFFFAOYSA-N 1-hydroxy-1-propan-2-yl-3-(3,4,5-trimethoxyphenyl)urea Chemical compound COC1=CC(NC(=O)N(O)C(C)C)=CC(OC)=C1OC GBUJJTWYBQXKMP-UHFFFAOYSA-N 0.000 claims description 2
- KIXWCQGCSDSZJP-UHFFFAOYSA-N 1-hydroxy-3-(3-methoxyphenyl)-1-methylurea Chemical compound COC1=CC=CC(NC(=O)N(C)O)=C1 KIXWCQGCSDSZJP-UHFFFAOYSA-N 0.000 claims description 2
- JFTXXIWGINAPRW-UHFFFAOYSA-N 1-hydroxy-3-(3-methylphenyl)-1-propan-2-ylurea Chemical compound CC(C)N(O)C(=O)NC1=CC=CC(C)=C1 JFTXXIWGINAPRW-UHFFFAOYSA-N 0.000 claims description 2
- ABSAVCDABIYUSR-UHFFFAOYSA-N 1-hydroxy-3-(4-methoxyphenyl)-1-propan-2-ylurea Chemical compound COC1=CC=C(NC(=O)N(O)C(C)C)C=C1 ABSAVCDABIYUSR-UHFFFAOYSA-N 0.000 claims description 2
- VMAJNRVBTRLLFF-UHFFFAOYSA-N 1-hydroxy-3-(4-methylsulfanylphenyl)-1-pentan-3-ylurea Chemical compound CCC(CC)N(O)C(=O)NC1=CC=C(SC)C=C1 VMAJNRVBTRLLFF-UHFFFAOYSA-N 0.000 claims description 2
- PVUSGHXDOQZRHB-UHFFFAOYSA-N 1-hydroxy-3-(4-methylsulfanylphenyl)-1-propan-2-ylurea Chemical compound CSC1=CC=C(NC(=O)N(O)C(C)C)C=C1 PVUSGHXDOQZRHB-UHFFFAOYSA-N 0.000 claims description 2
- GJHPFNVPBFZSBZ-UHFFFAOYSA-N 1-hydroxy-3-(4-methylsulfinylphenyl)-1-propan-2-ylurea Chemical compound CC(C)N(O)C(=O)NC1=CC=C(S(C)=O)C=C1 GJHPFNVPBFZSBZ-UHFFFAOYSA-N 0.000 claims description 2
- SRYYGLFBFPLVKS-UHFFFAOYSA-N 1-hydroxy-3-(4-methylsulfonylphenyl)-1-propan-2-ylurea Chemical compound CC(C)N(O)C(=O)NC1=CC=C(S(C)(=O)=O)C=C1 SRYYGLFBFPLVKS-UHFFFAOYSA-N 0.000 claims description 2
- ZKYGFQZYEHOHFT-UHFFFAOYSA-N 1-hydroxy-3-methyl-1-pentan-3-yl-3-phenylurea Chemical compound CCC(CC)N(O)C(=O)N(C)C1=CC=CC=C1 ZKYGFQZYEHOHFT-UHFFFAOYSA-N 0.000 claims description 2
- YXIQIWGBXUWPMP-UHFFFAOYSA-N 1-hydroxy-3-phenyl-1-propylurea Chemical compound CCCN(O)C(=O)NC1=CC=CC=C1 YXIQIWGBXUWPMP-UHFFFAOYSA-N 0.000 claims description 2
- XOUHVHLQDLQVGK-UHFFFAOYSA-N 3-(2,6-dimethylphenyl)-1-hydroxy-1-propan-2-ylurea Chemical compound CC(C)N(O)C(=O)NC1=C(C)C=CC=C1C XOUHVHLQDLQVGK-UHFFFAOYSA-N 0.000 claims description 2
- TUNLIDHDEAPGFH-UHFFFAOYSA-N 3-(2-chlorophenyl)-1-hydroxy-1-propan-2-ylurea Chemical compound CC(C)N(O)C(=O)NC1=CC=CC=C1Cl TUNLIDHDEAPGFH-UHFFFAOYSA-N 0.000 claims description 2
- UWRRNHUJMVRJQM-UHFFFAOYSA-N 3-(3-bromophenyl)-1-hydroxy-1-methylurea Chemical compound CN(O)C(=O)NC1=CC=CC(Br)=C1 UWRRNHUJMVRJQM-UHFFFAOYSA-N 0.000 claims description 2
- SSWQQXXNXZZMGI-UHFFFAOYSA-N 3-(3-fluorophenyl)-1-hydroxy-1-methylurea Chemical compound CN(O)C(=O)NC1=CC=CC(F)=C1 SSWQQXXNXZZMGI-UHFFFAOYSA-N 0.000 claims description 2
- PYOOIHLAZICISI-UHFFFAOYSA-N 3-(4-benzylphenyl)-1-hydroxy-1-pentan-3-ylurea Chemical compound C1=CC(NC(=O)N(O)C(CC)CC)=CC=C1CC1=CC=CC=C1 PYOOIHLAZICISI-UHFFFAOYSA-N 0.000 claims description 2
- KXNBJEAIJGHRTA-UHFFFAOYSA-N 3-(4-bromophenyl)-1-hydroxy-1-propan-2-ylurea Chemical compound CC(C)N(O)C(=O)NC1=CC=C(Br)C=C1 KXNBJEAIJGHRTA-UHFFFAOYSA-N 0.000 claims description 2
- LMSPXPMFWLBACP-UHFFFAOYSA-N 3-(4-fluorophenyl)-1-hydroxy-1-methylurea Chemical compound CN(O)C(=O)NC1=CC=C(F)C=C1 LMSPXPMFWLBACP-UHFFFAOYSA-N 0.000 claims description 2
- OZGAHZOKLMNWLQ-UHFFFAOYSA-N 3-(4-fluorophenyl)-1-hydroxy-1-propan-2-ylurea Chemical compound CC(C)N(O)C(=O)NC1=CC=C(F)C=C1 OZGAHZOKLMNWLQ-UHFFFAOYSA-N 0.000 claims description 2
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000000062 cyclohexylmethoxy group Chemical group [H]C([H])(O*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
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- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 2
- 230000008687 biosynthesis inhibition Effects 0.000 claims 2
- PXHXUXKVWDYSND-UHFFFAOYSA-N 1-(3,3-dimethylbutyl)-1-hydroxy-3-phenylurea Chemical compound CC(C)(C)CCN(O)C(=O)NC1=CC=CC=C1 PXHXUXKVWDYSND-UHFFFAOYSA-N 0.000 claims 1
- UVEHEHCJUFXWCZ-UHFFFAOYSA-N 1-dodecyl-1-hydroxy-3-phenylurea Chemical compound CCCCCCCCCCCCN(O)C(=O)NC1=CC=CC=C1 UVEHEHCJUFXWCZ-UHFFFAOYSA-N 0.000 claims 1
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- BFPVIYCFRMYRHI-UHFFFAOYSA-N 1-hydroxy-1-pentan-3-yl-3-[4-(3-phenylpropoxy)phenyl]urea Chemical compound C1=CC(NC(=O)N(O)C(CC)CC)=CC=C1OCCCC1=CC=CC=C1 BFPVIYCFRMYRHI-UHFFFAOYSA-N 0.000 claims 1
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- ITVQLDIOEIQRLO-UHFFFAOYSA-N 3-(2,5-dimethoxyphenyl)-1-hydroxy-1-propan-2-ylurea Chemical compound COC1=CC=C(OC)C(NC(=O)N(O)C(C)C)=C1 ITVQLDIOEIQRLO-UHFFFAOYSA-N 0.000 claims 1
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- KPYKRDVPHVGXMO-UHFFFAOYSA-N 3-[4-(cyclohexylmethoxy)phenyl]-1-hydroxy-1-pentan-3-ylurea Chemical compound C1=CC(NC(=O)N(O)C(CC)CC)=CC=C1OCC1CCCCC1 KPYKRDVPHVGXMO-UHFFFAOYSA-N 0.000 claims 1
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- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims 1
- OOBHKEXLUONANP-UHFFFAOYSA-N ethyl 6-[hydroxy(phenylcarbamoyl)amino]hexanoate Chemical compound CCOC(=O)CCCCCN(O)C(=O)NC1=CC=CC=C1 OOBHKEXLUONANP-UHFFFAOYSA-N 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
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- 125000002071 phenylalkoxy group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 55
- 230000002401 inhibitory effect Effects 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
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Classifications
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/17—Amides, e.g. hydroxamic acids having the group >N—C(O)—N< or >N—C(S)—N<, e.g. urea, thiourea, carmustine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
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US28601794A | 1994-08-04 | 1994-08-04 | |
US08/455,643 US5612377A (en) | 1994-08-04 | 1995-05-31 | Method of inhibiting leukotriene biosynthesis |
PCT/US1995/007667 WO1996003983A1 (en) | 1994-08-04 | 1995-07-14 | Inhibition of leukotriene biosynthesis with urea derivatives |
Publications (3)
Publication Number | Publication Date |
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NO970477D0 NO970477D0 (no) | 1997-02-03 |
NO970477L NO970477L (no) | 1997-03-14 |
NO315786B1 true NO315786B1 (no) | 2003-10-27 |
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Application Number | Title | Priority Date | Filing Date |
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NO19970477A NO315786B1 (no) | 1994-08-04 | 1997-02-03 | Inhibisjon av leukotrienbiosyntese med ureaderivater |
Country Status (19)
Country | Link |
---|---|
EP (1) | EP0777471B1 (de) |
JP (1) | JPH10503771A (de) |
AT (1) | ATE228359T1 (de) |
AU (1) | AU685980B2 (de) |
BR (1) | BR9508521A (de) |
CA (1) | CA2196701A1 (de) |
CZ (1) | CZ287034B6 (de) |
DE (1) | DE69528984T2 (de) |
DK (1) | DK0777471T3 (de) |
ES (1) | ES2185708T3 (de) |
FI (1) | FI970452A (de) |
HU (1) | HUT76830A (de) |
IL (1) | IL114646A (de) |
NO (1) | NO315786B1 (de) |
NZ (1) | NZ290236A (de) |
PL (1) | PL180668B1 (de) |
PT (1) | PT777471E (de) |
SK (1) | SK282777B6 (de) |
WO (1) | WO1996003983A1 (de) |
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Publication number | Priority date | Publication date | Assignee | Title |
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US6126919A (en) | 1997-02-07 | 2000-10-03 | 3M Innovative Properties Company | Biocompatible compounds for pharmaceutical drug delivery systems |
FR2880022B1 (fr) * | 2004-12-24 | 2007-08-24 | Mayoly Spindler Soc Par Action | Nouveaux derives de la n-hydroxy-n'-phenyluree et de la n-hydroxy-n'-phenylthiouree et leur utilisation comme inhibiteurs de la synthese de la melanine |
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Publication number | Priority date | Publication date | Assignee | Title |
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US5066658A (en) * | 1988-11-10 | 1991-11-19 | Ortho Pharmaceutical Corporation | Substituted hydroxyureas |
EP0456760A4 (en) * | 1989-02-01 | 1992-01-08 | Abbott Laboratories | Lipoxygenase inhibiting compounds |
JP2528741B2 (ja) * | 1991-01-09 | 1996-08-28 | ファイザー製薬株式会社 | オキサゾ―ル、チアゾ―ルおよびイミダゾ―ル化合物 |
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1995
- 1995-07-14 WO PCT/US1995/007667 patent/WO1996003983A1/en active IP Right Grant
- 1995-07-14 EP EP95926593A patent/EP0777471B1/de not_active Expired - Lifetime
- 1995-07-14 PT PT95926593T patent/PT777471E/pt unknown
- 1995-07-14 HU HU9700338A patent/HUT76830A/hu unknown
- 1995-07-14 NZ NZ290236A patent/NZ290236A/xx unknown
- 1995-07-14 SK SK110-97A patent/SK282777B6/sk unknown
- 1995-07-14 DK DK95926593T patent/DK0777471T3/da active
- 1995-07-14 AU AU30917/95A patent/AU685980B2/en not_active Ceased
- 1995-07-14 CA CA002196701A patent/CA2196701A1/en not_active Abandoned
- 1995-07-14 CZ CZ1997312A patent/CZ287034B6/cs not_active IP Right Cessation
- 1995-07-14 PL PL95318539A patent/PL180668B1/pl not_active IP Right Cessation
- 1995-07-14 BR BR9508521A patent/BR9508521A/pt not_active Application Discontinuation
- 1995-07-14 JP JP8506485A patent/JPH10503771A/ja not_active Withdrawn
- 1995-07-14 AT AT95926593T patent/ATE228359T1/de not_active IP Right Cessation
- 1995-07-14 DE DE69528984T patent/DE69528984T2/de not_active Expired - Fee Related
- 1995-07-14 ES ES95926593T patent/ES2185708T3/es not_active Expired - Lifetime
- 1995-07-18 IL IL11464695A patent/IL114646A/xx not_active IP Right Cessation
-
1997
- 1997-02-03 NO NO19970477A patent/NO315786B1/no unknown
- 1997-02-03 FI FI970452A patent/FI970452A/fi not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
EP0777471B1 (de) | 2002-11-27 |
PL180668B1 (pl) | 2001-03-30 |
ATE228359T1 (de) | 2002-12-15 |
CZ31297A3 (en) | 1997-09-17 |
PL318539A1 (en) | 1997-06-23 |
CZ287034B6 (en) | 2000-08-16 |
WO1996003983A1 (en) | 1996-02-15 |
IL114646A0 (en) | 1995-11-27 |
CA2196701A1 (en) | 1996-02-15 |
DE69528984D1 (de) | 2003-01-09 |
AU3091795A (en) | 1996-03-04 |
ES2185708T3 (es) | 2003-05-01 |
FI970452A0 (fi) | 1997-02-03 |
IL114646A (en) | 2000-02-29 |
EP0777471A1 (de) | 1997-06-11 |
SK11097A3 (en) | 1997-09-10 |
HUT76830A (en) | 1997-11-28 |
BR9508521A (pt) | 1997-10-28 |
DE69528984T2 (de) | 2003-09-04 |
JPH10503771A (ja) | 1998-04-07 |
MX9700860A (es) | 1997-10-31 |
NO970477L (no) | 1997-03-14 |
FI970452A (fi) | 1997-02-03 |
NO970477D0 (no) | 1997-02-03 |
SK282777B6 (sk) | 2002-12-03 |
NZ290236A (en) | 1998-12-23 |
AU685980B2 (en) | 1998-01-29 |
DK0777471T3 (da) | 2003-03-17 |
PT777471E (pt) | 2003-04-30 |
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