JP2003535820A5 - - Google Patents
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- JP2003535820A5 JP2003535820A5 JP2001567669A JP2001567669A JP2003535820A5 JP 2003535820 A5 JP2003535820 A5 JP 2003535820A5 JP 2001567669 A JP2001567669 A JP 2001567669A JP 2001567669 A JP2001567669 A JP 2001567669A JP 2003535820 A5 JP2003535820 A5 JP 2003535820A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- aryl
- heterocyclic
- heteroaryl
- chloro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000001072 heteroaryl group Chemical group 0.000 description 15
- 125000000623 heterocyclic group Chemical group 0.000 description 15
- 125000003118 aryl group Chemical group 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 150000002431 hydrogen Chemical class 0.000 description 6
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 229910052736 halogen Inorganic materials 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000003107 substituted aryl group Chemical group 0.000 description 4
- 206010040070 Septic Shock Diseases 0.000 description 3
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- -1 sinoline Chemical compound 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 206010006448 Bronchiolitis Diseases 0.000 description 2
- 102000019034 Chemokines Human genes 0.000 description 2
- 108010012236 Chemokines Proteins 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 206010021143 Hypoxia Diseases 0.000 description 2
- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- 229910003813 NRa Inorganic materials 0.000 description 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 208000014674 injury Diseases 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 230000001404 mediated effect Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 230000000414 obstructive effect Effects 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000008733 trauma Effects 0.000 description 2
- HTJMXYRLEDBSLT-UHFFFAOYSA-N 1,2,4,5-tetrazine Chemical compound C1=NN=CN=N1 HTJMXYRLEDBSLT-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- YGTAZGSLCXNBQL-UHFFFAOYSA-N 1,2,4-thiadiazole Chemical compound C=1N=CSN=1 YGTAZGSLCXNBQL-UHFFFAOYSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- WYMMZOJONYUXBY-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-sulfamoylphenyl)-3-(2,5-dimethylpyrazol-3-yl)urea Chemical compound CN1N=C(C)C=C1NC(=O)NC1=CC=C(Cl)C(S(N)(=O)=O)=C1O WYMMZOJONYUXBY-UHFFFAOYSA-N 0.000 description 1
- GJTZGKXLCMGZEV-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-sulfamoylphenyl)-3-(2-chloropyridin-3-yl)urea Chemical compound NS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2C(=NC=CC=2)Cl)=C1O GJTZGKXLCMGZEV-UHFFFAOYSA-N 0.000 description 1
- IWXOMPLYZYYFBT-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-sulfamoylphenyl)-3-(2-methylpyrazol-3-yl)urea Chemical compound CN1N=CC=C1NC(=O)NC1=CC=C(Cl)C(S(N)(=O)=O)=C1O IWXOMPLYZYYFBT-UHFFFAOYSA-N 0.000 description 1
- ZFMVWZXEPFTPFB-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-sulfamoylphenyl)-3-(2-methylpyridin-3-yl)urea Chemical compound CC1=NC=CC=C1NC(=O)NC1=CC=C(Cl)C(S(N)(=O)=O)=C1O ZFMVWZXEPFTPFB-UHFFFAOYSA-N 0.000 description 1
- LEUDLDKGXKPGRY-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-sulfamoylphenyl)-3-(3,5-dimethyl-1,2-oxazol-4-yl)urea Chemical compound CC1=NOC(C)=C1NC(=O)NC1=CC=C(Cl)C(S(N)(=O)=O)=C1O LEUDLDKGXKPGRY-UHFFFAOYSA-N 0.000 description 1
- BZZRIJYVKRNPQX-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-sulfamoylphenyl)-3-(3-methyl-1,2-oxazol-4-yl)urea Chemical compound CC1=NOC=C1NC(=O)NC1=CC=C(Cl)C(S(N)(=O)=O)=C1O BZZRIJYVKRNPQX-UHFFFAOYSA-N 0.000 description 1
- DJGLODQPHHIOKD-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-sulfamoylphenyl)-3-(3-phenylmethoxythieno[2,3-b]pyridin-2-yl)urea Chemical compound NS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC2=C(C3=CC=CN=C3S2)OCC=2C=CC=CC=2)=C1O DJGLODQPHHIOKD-UHFFFAOYSA-N 0.000 description 1
- TXXWLKHZJAJBAX-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-sulfamoylphenyl)-3-(3-phenyltriazol-4-yl)urea Chemical compound NS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2N(N=NC=2)C=2C=CC=CC=2)=C1O TXXWLKHZJAJBAX-UHFFFAOYSA-N 0.000 description 1
- HZTXUOWTYRWMSV-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-sulfamoylphenyl)-3-(5-methyl-1,2-oxazol-4-yl)urea Chemical compound O1N=CC(NC(=O)NC=2C(=C(C(Cl)=CC=2)S(N)(=O)=O)O)=C1C HZTXUOWTYRWMSV-UHFFFAOYSA-N 0.000 description 1
- ZVOWSDUJTNTJPT-UHFFFAOYSA-N 1-(4-chloro-2-hydroxy-3-sulfamoylphenyl)-3-pyridin-2-ylurea Chemical compound NS(=O)(=O)C1=C(Cl)C=CC(NC(=O)NC=2N=CC=CC=2)=C1O ZVOWSDUJTNTJPT-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 1
- SYOANZBNGDEJFH-UHFFFAOYSA-N 2,5-dihydro-1h-triazole Chemical compound C1NNN=C1 SYOANZBNGDEJFH-UHFFFAOYSA-N 0.000 description 1
- RLFZYIUUQBHRNV-UHFFFAOYSA-N 2,5-dihydrooxadiazole Chemical compound C1ONN=C1 RLFZYIUUQBHRNV-UHFFFAOYSA-N 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 206010033646 Acute and chronic pancreatitis Diseases 0.000 description 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
- 208000000884 Airway Obstruction Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000022306 Cerebral injury Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- 206010009137 Chronic sinusitis Diseases 0.000 description 1
- 208000015943 Coeliac disease Diseases 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 208000034656 Contusions Diseases 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 201000003883 Cystic fibrosis Diseases 0.000 description 1
- 206010012438 Dermatitis atopic Diseases 0.000 description 1
- 208000000059 Dyspnea Diseases 0.000 description 1
- 206010013975 Dyspnoeas Diseases 0.000 description 1
- 206010014561 Emphysema Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- 208000005232 Glossitis Diseases 0.000 description 1
- 206010019728 Hepatitis alcoholic Diseases 0.000 description 1
- 206010020591 Hypercapnia Diseases 0.000 description 1
- 206010058490 Hyperoxia Diseases 0.000 description 1
- 208000022559 Inflammatory bowel disease Diseases 0.000 description 1
- 208000029523 Interstitial Lung disease Diseases 0.000 description 1
- 206010022998 Irritability Diseases 0.000 description 1
- 206010024453 Ligament sprain Diseases 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- 208000034486 Multi-organ failure Diseases 0.000 description 1
- 208000010718 Multiple Organ Failure Diseases 0.000 description 1
- 206010051606 Necrotising colitis Diseases 0.000 description 1
- 206010030216 Oesophagitis Diseases 0.000 description 1
- 206010067472 Organising pneumonia Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical group C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 208000006399 Premature Obstetric Labor Diseases 0.000 description 1
- 208000003251 Pruritus Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 201000001263 Psoriatic Arthritis Diseases 0.000 description 1
- 208000036824 Psoriatic arthropathy Diseases 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 206010063837 Reperfusion injury Diseases 0.000 description 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
- 208000037656 Respiratory Sounds Diseases 0.000 description 1
- 208000000924 Right ventricular hypertrophy Diseases 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- 208000010040 Sprains and Strains Diseases 0.000 description 1
- 208000007107 Stomach Ulcer Diseases 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 208000032851 Subarachnoid Hemorrhage Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 206010044248 Toxic shock syndrome Diseases 0.000 description 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 206010046851 Uveitis Diseases 0.000 description 1
- 206010047115 Vasculitis Diseases 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- 206010047924 Wheezing Diseases 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
- 230000036428 airway hyperreactivity Effects 0.000 description 1
- 208000002353 alcoholic hepatitis Diseases 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 201000008937 atopic dermatitis Diseases 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 201000009267 bronchiectasis Diseases 0.000 description 1
- 210000003123 bronchiole Anatomy 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 208000034526 bruise Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 208000025997 central nervous system neoplasm Diseases 0.000 description 1
- 208000010353 central nervous system vasculitis Diseases 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 208000027157 chronic rhinosinusitis Diseases 0.000 description 1
- 201000009805 cryptogenic organizing pneumonia Diseases 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000006843 cycloalkyl-C1-5-alkyl Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 208000000718 duodenal ulcer Diseases 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 206010014599 encephalitis Diseases 0.000 description 1
- 208000006881 esophagitis Diseases 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 208000007565 gingivitis Diseases 0.000 description 1
- 208000024908 graft versus host disease Diseases 0.000 description 1
- 210000003958 hematopoietic stem cell Anatomy 0.000 description 1
- 208000006454 hepatitis Diseases 0.000 description 1
- 231100000283 hepatitis Toxicity 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 230000000222 hyperoxic effect Effects 0.000 description 1
- 208000018875 hypoxemia Diseases 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 206010025135 lupus erythematosus Diseases 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 208000029744 multiple organ dysfunction syndrome Diseases 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 208000004995 necrotizing enterocolitis Diseases 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 201000006195 perinatal necrotizing enterocolitis Diseases 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 208000005987 polymyositis Diseases 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 208000005069 pulmonary fibrosis Diseases 0.000 description 1
- 208000002815 pulmonary hypertension Diseases 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 230000000241 respiratory effect Effects 0.000 description 1
- 208000023504 respiratory system disease Diseases 0.000 description 1
- 208000037803 restenosis Diseases 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 201000000306 sarcoidosis Diseases 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- PWSBNTOBQBTNEJ-UHFFFAOYSA-N thieno[2,3-b]pyridine Chemical group C1=C[CH]C2=C=CSC2=N1 PWSBNTOBQBTNEJ-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Chemical group 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18841000P | 2000-03-10 | 2000-03-10 | |
| US60/188,410 | 2000-03-10 | ||
| PCT/US2001/007746 WO2001068568A2 (en) | 2000-03-10 | 2001-03-09 | Il-8 receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2003535820A JP2003535820A (ja) | 2003-12-02 |
| JP2003535820A5 true JP2003535820A5 (enExample) | 2008-04-24 |
Family
ID=22693024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001567669A Pending JP2003535820A (ja) | 2000-03-10 | 2001-03-09 | Ｉｌ−８受容体アンタゴニスト |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6608077B2 (enExample) |
| EP (1) | EP1261336B1 (enExample) |
| JP (1) | JP2003535820A (enExample) |
| KR (1) | KR20020083174A (enExample) |
| CN (1) | CN1635979A (enExample) |
| AR (1) | AR030273A1 (enExample) |
| AT (1) | ATE353215T1 (enExample) |
| AU (2) | AU4560601A (enExample) |
| BR (1) | BR0109002A (enExample) |
| CA (1) | CA2402891A1 (enExample) |
| CO (1) | CO5271660A1 (enExample) |
| CY (1) | CY1106514T1 (enExample) |
| CZ (1) | CZ20023007A3 (enExample) |
| DE (1) | DE60126480T2 (enExample) |
| DK (1) | DK1261336T3 (enExample) |
| ES (1) | ES2280350T3 (enExample) |
| HU (1) | HUP0302003A3 (enExample) |
| IL (1) | IL151431A0 (enExample) |
| MX (1) | MXPA02008818A (enExample) |
| MY (1) | MY133845A (enExample) |
| NO (1) | NO20024193D0 (enExample) |
| NZ (1) | NZ520912A (enExample) |
| PL (1) | PL363118A1 (enExample) |
| PT (1) | PT1261336E (enExample) |
| WO (1) | WO2001068568A2 (enExample) |
| ZA (1) | ZA200207216B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CY2010012I2 (el) * | 2000-05-25 | 2020-05-29 | Novartis Ag | Μιμητικα θρομβοποιητινης |
| AR030753A1 (es) * | 2000-09-25 | 2003-09-03 | Smithkline Beecham Corp | Uso de moduladores-proteina de il-8, groalfa, grobeta, grogamma, nap-2, y ena-78, para tratar infecciones viricas |
| GB0124848D0 (en) * | 2001-10-16 | 2001-12-05 | Celltech R&D Ltd | Chemical compounds |
| US20030236287A1 (en) * | 2002-05-03 | 2003-12-25 | Piotrowski David W. | Positive allosteric modulators of the nicotinic acetylcholine receptor |
| US7056925B2 (en) | 2002-08-13 | 2006-06-06 | Abbott Laboratories | Urea kinase inhibitors |
| TW200418812A (en) * | 2002-10-29 | 2004-10-01 | Smithkline Beecham Corp | IL-8 receptor antagonists |
| US7511042B2 (en) | 2003-12-03 | 2009-03-31 | Boehringer Ingelheim Pharmaceuticals, Inc. | Triazole compounds |
| JP2008517054A (ja) * | 2004-10-20 | 2008-05-22 | 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 |
| EP2010180A4 (en) * | 2006-04-21 | 2010-10-13 | Glaxosmithkline Llc | IL-8 RECEPTOR ANTAGONISTS |
| CN101472477B (zh) * | 2006-04-21 | 2013-02-20 | 史密丝克莱恩比彻姆公司 | Il-8受体拮抗剂 |
| CL2007001829A1 (es) * | 2006-06-23 | 2008-01-25 | Smithkline Beecham Corp | P-toluensulfonato de n-[4-cloro-2-hidroxi-3-(piperazina-1-sulfonil)fenil]-n-(2-cloro-3-fluorofenil)urea;procedimiento de preparacion;composicion farmaceutica;combinacion farmaceutica;y uso en el tratamiento de una enfermedad mediada por la quiimioquina il-8, tales como asma y epoc. |
| RU2364405C1 (ru) * | 2008-04-10 | 2009-08-20 | Леонид Борисович Лазебник | Способ лечения воспалительных заболеваний кишечника |
| CN107522641B (zh) * | 2016-06-22 | 2020-05-05 | 复旦大学 | 联芳基脲类衍生物或其盐及其制备方法和用途 |
| WO2017219935A1 (zh) | 2016-06-22 | 2017-12-28 | 复旦大学 | 联芳基脲类衍生物或其盐及其制备方法和用途 |
| WO2019137484A1 (zh) * | 2018-01-11 | 2019-07-18 | 南京明德新药研发股份有限公司 | Cxcr2拮抗剂 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1996025157A1 (en) * | 1995-02-17 | 1996-08-22 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| WO1997049680A1 (en) * | 1996-06-27 | 1997-12-31 | Smithkline Beecham Corporation | Il-8 receptor antagonists |
| UY25842A1 (es) * | 1998-12-16 | 2001-04-30 | Smithkline Beecham Corp | Antagonistas de receptores de il-8 |
-
2001
- 2001-03-08 AR ARP010101098A patent/AR030273A1/es not_active Application Discontinuation
- 2001-03-08 MY MYPI20011072A patent/MY133845A/en unknown
- 2001-03-09 MX MXPA02008818A patent/MXPA02008818A/es not_active Application Discontinuation
- 2001-03-09 CA CA002402891A patent/CA2402891A1/en not_active Abandoned
- 2001-03-09 AU AU4560601A patent/AU4560601A/xx active Pending
- 2001-03-09 BR BR0109002-0A patent/BR0109002A/pt not_active IP Right Cessation
- 2001-03-09 AT AT01918542T patent/ATE353215T1/de not_active IP Right Cessation
- 2001-03-09 PT PT01918542T patent/PT1261336E/pt unknown
- 2001-03-09 DK DK01918542T patent/DK1261336T3/da active
- 2001-03-09 CZ CZ20023007A patent/CZ20023007A3/cs unknown
- 2001-03-09 EP EP01918542A patent/EP1261336B1/en not_active Expired - Lifetime
- 2001-03-09 PL PL01363118A patent/PL363118A1/xx not_active Application Discontinuation
- 2001-03-09 AU AU2001245606A patent/AU2001245606B2/en not_active Ceased
- 2001-03-09 DE DE60126480T patent/DE60126480T2/de not_active Expired - Fee Related
- 2001-03-09 IL IL15143101A patent/IL151431A0/xx unknown
- 2001-03-09 ES ES01918542T patent/ES2280350T3/es not_active Expired - Lifetime
- 2001-03-09 WO PCT/US2001/007746 patent/WO2001068568A2/en not_active Ceased
- 2001-03-09 US US10/220,772 patent/US6608077B2/en not_active Expired - Fee Related
- 2001-03-09 HU HU0302003A patent/HUP0302003A3/hu unknown
- 2001-03-09 NZ NZ520912A patent/NZ520912A/en unknown
- 2001-03-09 KR KR1020027011807A patent/KR20020083174A/ko not_active Ceased
- 2001-03-09 CN CNA018062563A patent/CN1635979A/zh active Pending
- 2001-03-09 JP JP2001567669A patent/JP2003535820A/ja active Pending
- 2001-03-12 CO CO01019686A patent/CO5271660A1/es not_active Application Discontinuation
-
2002
- 2002-09-03 NO NO20024193A patent/NO20024193D0/no unknown
- 2002-09-09 ZA ZA200207216A patent/ZA200207216B/en unknown
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2007
- 2007-04-16 CY CY20071100520T patent/CY1106514T1/el unknown
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