CZ20014471A3 - Antagonisté IL-8 receptoru - Google Patents

Info

Publication number

CZ20014471A3

CZ20014471A3 CZ20014471A CZ20014471A CZ20014471A3 CZ 20014471 A3 CZ20014471 A3 CZ 20014471A3 CZ 20014471 A CZ20014471 A CZ 20014471A CZ 20014471 A CZ20014471 A CZ 20014471A CZ 20014471 A3 CZ20014471 A3 CZ 20014471A3

Authority

CZ

Czechia

Prior art keywords

group

carbon atoms

urea

hydroxy

alkyl

Prior art date

1999-06-16

Links

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• Global Dossier
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• 102000010681 interleukin-8 receptors Human genes 0.000 title description 5
• 108010038415 interleukin-8 receptors Proteins 0.000 title description 4
• 239000002464 receptor antagonist Substances 0.000 title 1
• 229940044551 receptor antagonist Drugs 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 156
• 201000010099 disease Diseases 0.000 claims abstract description 33
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 33
• 150000003839 salts Chemical class 0.000 claims abstract description 29
• 230000001404 mediated effect Effects 0.000 claims abstract description 18
• 102000012740 beta Adrenergic Receptors Human genes 0.000 claims abstract description 14
• 108010079452 beta Adrenergic Receptors Proteins 0.000 claims abstract description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 425
• 125000000217 alkyl group Chemical group 0.000 claims description 182
• -1 -NHS (O) 2 Rb Chemical group 0.000 claims description 166
• 125000003342 alkenyl group Chemical group 0.000 claims description 122
• 229910052739 hydrogen Inorganic materials 0.000 claims description 78
• 125000000623 heterocyclic group Chemical group 0.000 claims description 75
• 229910052736 halogen Inorganic materials 0.000 claims description 73
• 239000001257 hydrogen Substances 0.000 claims description 67
• 125000003545 alkoxy group Chemical group 0.000 claims description 58
• 125000001072 heteroaryl group Chemical group 0.000 claims description 58
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 51
• 125000001424 substituent group Chemical group 0.000 claims description 49
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 47
• 150000002367 halogens Chemical class 0.000 claims description 42
• 125000003118 aryl group Chemical group 0.000 claims description 41
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
• 229910052717 sulfur Chemical group 0.000 claims description 33
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 32
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
• 125000003107 substituted aryl group Chemical group 0.000 claims description 29
• 229910052757 nitrogen Inorganic materials 0.000 claims description 25
• 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 24
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
• 229910052760 oxygen Inorganic materials 0.000 claims description 23
• 239000001301 oxygen Substances 0.000 claims description 23
• 125000005018 aryl alkenyl group Chemical group 0.000 claims description 22
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 21
• 125000005843 halogen group Chemical group 0.000 claims description 21
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 21
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 18
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 17
• 125000004104 aryloxy group Chemical group 0.000 claims description 17
• 125000005415 substituted alkoxy group Chemical group 0.000 claims description 15
• IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 14
• 125000005842 heteroatom Chemical group 0.000 claims description 13
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
• 125000004434 sulfur atom Chemical group 0.000 claims description 13
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
• 239000011593 sulfur Chemical group 0.000 claims description 12
• 241000124008 Mammalia Species 0.000 claims description 11
• 125000004429 atom Chemical group 0.000 claims description 11
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
• 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
• 229910052799 carbon Inorganic materials 0.000 claims description 10
• 125000000524 functional group Chemical group 0.000 claims description 8
• VIKJECVSALYBJB-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(4-cyano-2-hydroxyphenyl)urea Chemical compound OC1=CC(C#N)=CC=C1NC(=O)NC1=CC=CC=C1Br VIKJECVSALYBJB-UHFFFAOYSA-N 0.000 claims description 7
• 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 7
• 108010018976 Interleukin-8A Receptors Proteins 0.000 claims description 6
• 241000700605 Viruses Species 0.000 claims description 6
• JYYRLQNSIZPUPF-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(2-hydroxy-4-nitrophenyl)thiourea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=S)NC1=CC=CC=C1Br JYYRLQNSIZPUPF-UHFFFAOYSA-N 0.000 claims description 5
• MPBMQOWOKKDSFC-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(3-chloro-2-hydroxyphenyl)urea Chemical compound OC1=C(Cl)C=CC=C1NC(=O)NC1=CC=CC=C1Br MPBMQOWOKKDSFC-UHFFFAOYSA-N 0.000 claims description 5
• DNYOWRQDSNGAQQ-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(3-cyano-2-hydroxy-4-methylphenyl)urea Chemical compound OC1=C(C#N)C(C)=CC=C1NC(=O)NC1=CC=CC=C1Br DNYOWRQDSNGAQQ-UHFFFAOYSA-N 0.000 claims description 5
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
• 125000002950 monocyclic group Chemical group 0.000 claims description 5
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
• CBPGTUOXTFTWTE-UHFFFAOYSA-N 1-(1,3-benzodioxol-4-yl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC2=C1OCO2 CBPGTUOXTFTWTE-UHFFFAOYSA-N 0.000 claims description 4
• PEBCQTKZVQCXJP-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(3,4-dichloro-2-hydroxyphenyl)urea Chemical compound OC1=C(Cl)C(Cl)=CC=C1NC(=O)NC1=CC=CC=C1Br PEBCQTKZVQCXJP-UHFFFAOYSA-N 0.000 claims description 4
• XJGIXEVHERZBQV-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(3-cyano-2-hydroxyphenyl)urea Chemical compound C1=CC=C(C#N)C(O)=C1NC(=O)NC1=CC=CC=C1Br XJGIXEVHERZBQV-UHFFFAOYSA-N 0.000 claims description 4
• IGNKQJCDASZUBP-UHFFFAOYSA-N 1-(2-bromophenyl)-3-[2-hydroxy-3-(trifluoromethyl)phenyl]urea Chemical compound C1=CC=C(C(F)(F)F)C(O)=C1NC(=O)NC1=CC=CC=C1Br IGNKQJCDASZUBP-UHFFFAOYSA-N 0.000 claims description 4
• MHEWCJHSRKVNIF-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(2-phenoxyphenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1OC1=CC=CC=C1 MHEWCJHSRKVNIF-UHFFFAOYSA-N 0.000 claims description 4
• ZHFMJOHHDQGOTA-UHFFFAOYSA-N 1-(4-cyano-2-hydroxyphenyl)-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC=C(C#N)C=C1O ZHFMJOHHDQGOTA-UHFFFAOYSA-N 0.000 claims description 4
• BNWWISXBCWURFH-UHFFFAOYSA-N 3-[(2-bromophenyl)carbamoylamino]-2-hydroxy-n-phenylbenzamide Chemical compound C1=CC=C(C(=O)NC=2C=CC=CC=2)C(O)=C1NC(=O)NC1=CC=CC=C1Br BNWWISXBCWURFH-UHFFFAOYSA-N 0.000 claims description 4
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 4
• 230000000241 respiratory effect Effects 0.000 claims description 4
• 150000003573 thiols Chemical group 0.000 claims description 4
• UUDFKBXAWIEQJG-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(2-hydroxy-3-nitrophenyl)urea Chemical compound C1=CC=C([N+]([O-])=O)C(O)=C1NC(=O)NC1=CC=CC=C1Br UUDFKBXAWIEQJG-UHFFFAOYSA-N 0.000 claims description 3
• MQBZVUNNWUIPMK-UHFFFAOYSA-N 1-(2-bromophenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1Br MQBZVUNNWUIPMK-UHFFFAOYSA-N 0.000 claims description 3
• PMMYTIINRJXKSU-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(2-iodophenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1I PMMYTIINRJXKSU-UHFFFAOYSA-N 0.000 claims description 3
• GTJXCKKJNGSTCK-UHFFFAOYSA-N 1-(3-chloro-2-methoxyphenyl)-3-(2-hydroxy-4-nitrophenyl)urea Chemical compound COC1=C(Cl)C=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1O GTJXCKKJNGSTCK-UHFFFAOYSA-N 0.000 claims description 3
• IAIFWAOFGOIHNN-UHFFFAOYSA-N 1-(3-cyano-2-hydroxyphenyl)-3-(2,3-dichlorophenyl)urea Chemical compound C1=CC=C(C#N)C(O)=C1NC(=O)NC1=CC=CC(Cl)=C1Cl IAIFWAOFGOIHNN-UHFFFAOYSA-N 0.000 claims description 3
• PSODDICKDGEFJX-UHFFFAOYSA-N 1-(4-cyano-2-hydroxyphenyl)-3-[2-(trifluoromethyl)phenyl]urea Chemical compound OC1=CC(C#N)=CC=C1NC(=O)NC1=CC=CC=C1C(F)(F)F PSODDICKDGEFJX-UHFFFAOYSA-N 0.000 claims description 3
• 230000033115 angiogenesis Effects 0.000 claims description 3
• 210000003958 hematopoietic stem cell Anatomy 0.000 claims description 3
• 201000004792 malaria Diseases 0.000 claims description 3
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 3
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 3
• DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 2
• KNPLCJZGNRGZAN-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1O KNPLCJZGNRGZAN-UHFFFAOYSA-N 0.000 claims description 2
• MPSVIJAQCVNHHQ-UHFFFAOYSA-N 1-(2-hydroxy-4-nitrophenyl)-3-(2-phenylphenyl)urea Chemical compound OC1=CC([N+]([O-])=O)=CC=C1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 MPSVIJAQCVNHHQ-UHFFFAOYSA-N 0.000 claims description 2
• YZAZGBOPFBFDAC-UHFFFAOYSA-N 1-(4-cyano-2-hydroxyphenyl)-3-(2-phenylphenyl)urea Chemical compound OC1=CC(C#N)=CC=C1NC(=O)NC1=CC=CC=C1C1=CC=CC=C1 YZAZGBOPFBFDAC-UHFFFAOYSA-N 0.000 claims description 2
• 241000723346 Cinnamomum camphora Species 0.000 claims description 2
• 229960000846 camphor Drugs 0.000 claims description 2
• 229930008380 camphor Natural products 0.000 claims description 2
• 208000006454 hepatitis Diseases 0.000 claims description 2
• 125000004001 thioalkyl group Chemical group 0.000 claims description 2
• 125000005000 thioaryl group Chemical group 0.000 claims description 2
• 241001529453 unidentified herpesvirus Species 0.000 claims description 2
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
• PEZPHMOCGURMEM-UHFFFAOYSA-N (2,3-dichlorophenyl)urea Chemical compound NC(=O)NC1=CC=CC(Cl)=C1Cl PEZPHMOCGURMEM-UHFFFAOYSA-N 0.000 claims 1
• 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims 1
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
• UDJXJZJIZIAVBN-UHFFFAOYSA-N 1-(3,4-dichloro-2-hydroxyphenyl)-1-(2-methoxyphenyl)urea Chemical compound COC1=CC=CC=C1N(C(N)=O)C1=CC=C(Cl)C(Cl)=C1O UDJXJZJIZIAVBN-UHFFFAOYSA-N 0.000 claims 1
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• 238000000034 method Methods 0.000 abstract description 169
• 108090001007 Interleukin-8 Proteins 0.000 abstract description 5
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• 102000019034 Chemokines Human genes 0.000 abstract 3
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 561
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 388
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