OA11079A - Sulfonyl urea derivatives and their use in the control of interleukin-1 activity - Google Patents

Sulfonyl urea derivatives and their use in the control of interleukin-1 activity Download PDF

Info

Publication number: OA11079A
Authority: OA; OAPI
Prior art keywords: alkyl; hydrogen; hydroxy; urea; group
Prior art date: 1997-01-29

Application number

OA9900165A

Other languages

English (en)

Inventor

Mark Anthony Dombroski

James Frederick Eggler

Original Assignee

Pfizer

Priority date (The priority date 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 date listed.)

1997-01-29

Filing date

1999-07-23

Publication date

2002-03-14

1999-07-23 Application filed by Pfizer filed Critical Pfizer

2002-03-14 Publication of OA11079A publication Critical patent/OA11079A/en

Links

108010002352 Interleukin-1 Proteins 0.000 title claims abstract description 9
102000000589 Interleukin-1 Human genes 0.000 title description 6
230000000694 effects Effects 0.000 title description 4
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 59
125000003118 aryl group Chemical group 0.000 claims abstract description 35
201000010099 disease Diseases 0.000 claims abstract description 12
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 12
238000011282 treatment Methods 0.000 claims abstract description 8
208000009525 Myocarditis Diseases 0.000 claims abstract description 7
206010001052 Acute respiratory distress syndrome Diseases 0.000 claims abstract description 6
206010006895 Cachexia Diseases 0.000 claims abstract description 6
206010016654 Fibrosis Diseases 0.000 claims abstract description 6
206010018364 Glomerulonephritis Diseases 0.000 claims abstract description 6
208000009329 Graft vs Host Disease Diseases 0.000 claims abstract description 6
241000124008 Mammalia Species 0.000 claims abstract description 6
206010028980 Neoplasm Diseases 0.000 claims abstract description 6
206010033645 Pancreatitis Diseases 0.000 claims abstract description 6
208000013616 Respiratory Distress Syndrome Diseases 0.000 claims abstract description 6
206010040070 Septic Shock Diseases 0.000 claims abstract description 6
201000009594 Systemic Scleroderma Diseases 0.000 claims abstract description 6
206010042953 Systemic sclerosis Diseases 0.000 claims abstract description 6
206010047115 Vasculitis Diseases 0.000 claims abstract description 6
208000027418 Wounds and injury Diseases 0.000 claims abstract description 6
230000001154 acute effect Effects 0.000 claims abstract description 6
208000038016 acute inflammation Diseases 0.000 claims abstract description 6
230000006022 acute inflammation Effects 0.000 claims abstract description 6
208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims abstract description 6
201000000028 adult respiratory distress syndrome Diseases 0.000 claims abstract description 6
206010003246 arthritis Diseases 0.000 claims abstract description 6
230000003305 autocrine Effects 0.000 claims abstract description 6
208000003167 cholangitis Diseases 0.000 claims abstract description 6
208000037976 chronic inflammation Diseases 0.000 claims abstract description 6
230000006020 chronic inflammation Effects 0.000 claims abstract description 6
230000007882 cirrhosis Effects 0.000 claims abstract description 6
208000019425 cirrhosis of liver Diseases 0.000 claims abstract description 6
206010009887 colitis Diseases 0.000 claims abstract description 6
230000006378 damage Effects 0.000 claims abstract description 6
206010014599 encephalitis Diseases 0.000 claims abstract description 6
206010014665 endocarditis Diseases 0.000 claims abstract description 6
208000024908 graft versus host disease Diseases 0.000 claims abstract description 6
239000003102 growth factor Substances 0.000 claims abstract description 6
208000006454 hepatitis Diseases 0.000 claims abstract description 6
231100000283 hepatitis Toxicity 0.000 claims abstract description 6
208000014674 injury Diseases 0.000 claims abstract description 6
208000011379 keloid formation Diseases 0.000 claims abstract description 6
201000006417 multiple sclerosis Diseases 0.000 claims abstract description 6
238000009527 percussion Methods 0.000 claims abstract description 6
208000008494 pericarditis Diseases 0.000 claims abstract description 6
230000036303 septic shock Effects 0.000 claims abstract description 6
201000001320 Atherosclerosis Diseases 0.000 claims abstract description 5
208000023275 Autoimmune disease Diseases 0.000 claims abstract description 5
208000006313 Delayed Hypersensitivity Diseases 0.000 claims abstract description 5
208000001132 Osteoporosis Diseases 0.000 claims abstract description 5
206010063837 Reperfusion injury Diseases 0.000 claims abstract description 5
208000007893 Salpingitis Diseases 0.000 claims abstract description 5
206010052779 Transplant rejections Diseases 0.000 claims abstract description 5
208000029523 Interstitial Lung disease Diseases 0.000 claims abstract description 4
201000009906 Meningitis Diseases 0.000 claims abstract description 3
239000004202 carbamide Substances 0.000 claims description 128
125000000217 alkyl group Chemical group 0.000 claims description 116
239000001257 hydrogen Substances 0.000 claims description 89
229910052739 hydrogen Inorganic materials 0.000 claims description 89
125000005843 halogen group Chemical group 0.000 claims description 62
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 38
-1 hydroxymethylene Chemical group 0.000 claims description 36
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
239000001301 oxygen Substances 0.000 claims description 28
229910052760 oxygen Inorganic materials 0.000 claims description 28
125000003545 alkoxy group Chemical group 0.000 claims description 27
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
235000001508 sulfur Nutrition 0.000 claims description 17
125000001072 heteroaryl group Chemical group 0.000 claims description 16
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
239000011593 sulfur Substances 0.000 claims description 15
229910052717 sulfur Inorganic materials 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 14
150000002431 hydrogen Chemical group 0.000 claims description 13
125000004414 alkyl thio group Chemical group 0.000 claims description 12
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 9
238000000034 method Methods 0.000 claims description 9
125000004423 acyloxy group Chemical group 0.000 claims description 8
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 8
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
125000005110 aryl thio group Chemical group 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000005936 piperidyl group Chemical group 0.000 claims description 8
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 7
125000003282 alkyl amino group Chemical group 0.000 claims description 7
125000005135 aryl sulfinyl group Chemical group 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
125000004442 acylamino group Chemical group 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
125000005241 heteroarylamino group Chemical group 0.000 claims description 6
125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
208000024827 Alzheimer disease Diseases 0.000 claims description 5
229910014585 C2-Ce Inorganic materials 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 5
125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 4
125000001769 aryl amino group Chemical group 0.000 claims description 4
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 4
125000005145 cycloalkylaminosulfonyl group Chemical group 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000005368 heteroarylthio group Chemical group 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
RZNNEQHIXCRCKM-UHFFFAOYSA-N 4-(2-hydroxypropan-2-yl)furan-2-sulfonamide Chemical compound CC(C)(O)C1=COC(S(N)(=O)=O)=C1 RZNNEQHIXCRCKM-UHFFFAOYSA-N 0.000 claims description 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
101100001672 Emericella variicolor andG gene Chemical group 0.000 claims description 3
125000005035 acylthio group Chemical group 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000002541 furyl group Chemical group 0.000 claims description 3
230000005764 inhibitory process Effects 0.000 claims description 3
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 3
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
HUUSXLKCTQDPGL-UHFFFAOYSA-N 1-(1,2,3,5,6,7-hexahydro-s-indacen-4-yl)-3-[4-(2-hydroxypropan-2-yl)furan-2-yl]sulfonylurea Chemical compound CC(C)(O)C1=COC(S(=O)(=O)NC(=O)NC=2C=3CCCC=3C=C3CCCC3=2)=C1 HUUSXLKCTQDPGL-UHFFFAOYSA-N 0.000 claims description 2
GGWYDFQWIFFOSI-UHFFFAOYSA-N 1-(4-acetylfuran-2-yl)sulfonyl-3-(1,2,3,5,6,7-hexahydro-s-indacen-4-yl)urea Chemical compound CC(=O)C1=COC(S(=O)(=O)NC(=O)NC=2C=3CCCC=3C=C3CCCC3=2)=C1 GGWYDFQWIFFOSI-UHFFFAOYSA-N 0.000 claims description 2
101100509371 Arabidopsis thaliana CHR11 gene Proteins 0.000 claims description 2
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 20
125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims 2
230000015271 coagulation Effects 0.000 claims 2
238000005345 coagulation Methods 0.000 claims 2
125000006528 (C2-C6) alkyl group Chemical group 0.000 claims 1
NQUWYENCXXXALZ-UHFFFAOYSA-N 1-(1,2,3,5,6,7-hexahydrodicyclopenta[2,1-b:2',1'-f]pyridin-8-yl)-3-[4-(2-hydroxypropan-2-yl)furan-2-yl]sulfonylurea Chemical compound CC(C)(O)C1=COC(S(=O)(=O)NC(=O)NC=2C=3CCCC=3N=C3CCCC3=2)=C1 NQUWYENCXXXALZ-UHFFFAOYSA-N 0.000 claims 1
MRKXXRUHPFFURP-UHFFFAOYSA-N 1-[2,6-di(propan-2-yl)phenyl]-3-[4-(2-hydroxypropan-2-yl)furan-2-yl]sulfonylurea Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NC(=O)NS(=O)(=O)C1=CC(C(C)(C)O)=CO1 MRKXXRUHPFFURP-UHFFFAOYSA-N 0.000 claims 1
SKRPFWPDHPSIJV-UHFFFAOYSA-N 1-[2,6-di(propan-2-yl)phenyl]-3-[4-(2-hydroxypropan-2-yl)thiophen-2-yl]sulfonylurea Chemical compound CC(C)C1=CC=CC(C(C)C)=C1NC(=O)NS(=O)(=O)C1=CC(C(C)(C)O)=CS1 SKRPFWPDHPSIJV-UHFFFAOYSA-N 0.000 claims 1
YAJHGUJUZWRUCH-UHFFFAOYSA-N 1-[4-chloro-2,6-di(propan-2-yl)phenyl]-3-[2-fluoro-5-(2-methyl-1,3-dioxolan-2-yl)phenyl]sulfonylurea Chemical compound CC(C)C1=CC(Cl)=CC(C(C)C)=C1NC(=O)NS(=O)(=O)C1=CC(C2(C)OCCO2)=CC=C1F YAJHGUJUZWRUCH-UHFFFAOYSA-N 0.000 claims 1
101100495912 Arabidopsis thaliana CHR12 gene Proteins 0.000 claims 1
KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
125000004193 piperazinyl group Chemical group 0.000 claims 1
125000005505 thiomorpholino group Chemical group 0.000 claims 1
208000009190 disseminated intravascular coagulation Diseases 0.000 abstract description 4
206010067584 Type 1 diabetes mellitus Diseases 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 84
239000000243 solution Substances 0.000 description 77
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 72
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 65
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
238000002360 preparation method Methods 0.000 description 48
LYAWGVFUGRUFEO-UHFFFAOYSA-N 5-chloro-2-isocyanato-1,3-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC(Cl)=CC(C(C)C)=C1N=C=O LYAWGVFUGRUFEO-UHFFFAOYSA-N 0.000 description 42
239000000203 mixture Substances 0.000 description 42
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
235000019439 ethyl acetate Nutrition 0.000 description 28
229940093499 ethyl acetate Drugs 0.000 description 28
FEUFNKALUGDEMQ-UHFFFAOYSA-N 2-isocyanato-1,3-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC(C(C)C)=C1N=C=O FEUFNKALUGDEMQ-UHFFFAOYSA-N 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 23
239000007787 solid Substances 0.000 description 23
125000002887 hydroxy group Chemical group [H]O* 0.000 description 20
229940073584 methylene chloride Drugs 0.000 description 20
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
210000004027 cell Anatomy 0.000 description 14
229960004132 diethyl ether Drugs 0.000 description 14
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 13
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
238000003756 stirring Methods 0.000 description 12
MJTPVXZNGZLGLN-UHFFFAOYSA-N 5-bromo-2-isocyanato-1,3-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC(Br)=CC(C(C)C)=C1N=C=O MJTPVXZNGZLGLN-UHFFFAOYSA-N 0.000 description 11
235000013877 carbamide Nutrition 0.000 description 11
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 10
229960000583 acetic acid Drugs 0.000 description 10
239000012948 isocyanate Substances 0.000 description 10
238000010992 reflux Methods 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 9
229940124530 sulfonamide Drugs 0.000 description 9
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
235000011054 acetic acid Nutrition 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
239000012267 brine Substances 0.000 description 8
235000011167 hydrochloric acid Nutrition 0.000 description 8
229960000443 hydrochloric acid Drugs 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
235000011121 sodium hydroxide Nutrition 0.000 description 8
229940083608 sodium hydroxide Drugs 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
ZLZNHLVBJWGUCV-UHFFFAOYSA-N 3-acetylbenzenesulfonamide Chemical compound CC(=O)C1=CC=CC(S(N)(=O)=O)=C1 ZLZNHLVBJWGUCV-UHFFFAOYSA-N 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
239000002002 slurry Substances 0.000 description 7
229960003010 sodium sulfate Drugs 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
235000011114 ammonium hydroxide Nutrition 0.000 description 6
150000002513 isocyanates Chemical class 0.000 description 6
210000001616 monocyte Anatomy 0.000 description 6
238000012545 processing Methods 0.000 description 6
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YDOAPWWZEHJLOL-UHFFFAOYSA-N 3-(tert-butylsulfamoyl)benzenesulfonyl chloride Chemical compound CC(C)(C)NS(=O)(=O)C1=CC=CC(S(Cl)(=O)=O)=C1 YDOAPWWZEHJLOL-UHFFFAOYSA-N 0.000 description 5
108090000695 Cytokines Proteins 0.000 description 5
102000004127 Cytokines Human genes 0.000 description 5
239000012259 ether extract Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
239000001632 sodium acetate Substances 0.000 description 5
235000017281 sodium acetate Nutrition 0.000 description 5
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
PTCFLPVOXDDUJB-UHFFFAOYSA-N 3-(1-hydroxyethyl)benzenesulfonamide Chemical compound CC(O)C1=CC=CC(S(N)(=O)=O)=C1 PTCFLPVOXDDUJB-UHFFFAOYSA-N 0.000 description 4
GXHWHRYDHGDHGB-UHFFFAOYSA-N 3-(tert-butylsulfamoyl)benzenesulfonic acid Chemical compound CC(C)(C)NS(=O)(=O)C1=CC=CC(S(O)(=O)=O)=C1 GXHWHRYDHGDHGB-UHFFFAOYSA-N 0.000 description 4
MGPHDXOVGHRZJB-UHFFFAOYSA-N 3-methylsulfanylbenzenesulfonamide Chemical compound CSC1=CC=CC(S(N)(=O)=O)=C1 MGPHDXOVGHRZJB-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
108091005804 Peptidases Proteins 0.000 description 4
239000004365 Protease Substances 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 4
239000008346 aqueous phase Substances 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000011084 recovery Methods 0.000 description 4
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
238000012360 testing method Methods 0.000 description 4
JSRLURSZEMLAFO-UHFFFAOYSA-N 1,3-dibromobenzene Chemical compound BrC1=CC=CC(Br)=C1 JSRLURSZEMLAFO-UHFFFAOYSA-N 0.000 description 3
DMBDLUOINUAOAF-UHFFFAOYSA-N 3,5-diacetylbenzenesulfonamide Chemical compound CC(=O)C1=CC(C(C)=O)=CC(S(N)(=O)=O)=C1 DMBDLUOINUAOAF-UHFFFAOYSA-N 0.000 description 3
HMFYZZFUJIBWKA-UHFFFAOYSA-N 3-(1-hydroxycyclopentyl)benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC(C2(O)CCCC2)=C1 HMFYZZFUJIBWKA-UHFFFAOYSA-N 0.000 description 3
KCCHKLXPMKGBPF-UHFFFAOYSA-N 3-(2-hydroxypropan-2-yl)benzenesulfonamide Chemical compound CC(C)(O)C1=CC=CC(S(N)(=O)=O)=C1 KCCHKLXPMKGBPF-UHFFFAOYSA-N 0.000 description 3
MRMLQMUKWMKZSC-UHFFFAOYSA-N 3-methylsulfinylbenzenesulfonamide Chemical compound CS(=O)C1=CC=CC(S(N)(=O)=O)=C1 MRMLQMUKWMKZSC-UHFFFAOYSA-N 0.000 description 3
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Classifications

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- 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
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/64—Sulfur atoms
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
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- C07C311/60—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea having sulfur atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings having nitrogen atoms of the sulfonylurea groups bound to carbon atoms of six-membered aromatic rings
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- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
- C07C323/67—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfonamide groups, bound to the carbon skeleton
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
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- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C—CHEMISTRY; METALLURGY
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

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Pharmacology & Pharmacy (AREA)
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Rheumatology (AREA)
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OA9900165A 1997-01-29 1999-07-23 Sulfonyl urea derivatives and their use in the control of interleukin-1 activity OA11079A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US3697997P	1997-01-29	1997-01-29

Publications (1)

Publication Number	Publication Date
OA11079A true OA11079A (en)	2002-03-14

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ID=21891776

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA9900165A OA11079A (en)	1997-01-29	1999-07-23	Sulfonyl urea derivatives and their use in the control of interleukin-1 activity

Country Status (40)

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US (2)	US6166064A (de)
EP (1)	EP0964849B1 (de)
JP (1)	JP3573757B2 (de)
KR (1)	KR100324058B1 (de)
CN (1)	CN1127479C (de)
AP (1)	AP929A (de)
AR (1)	AR011093A1 (de)
AT (2)	ATE242208T1 (de)
AU (1)	AU723895B2 (de)
BG (1)	BG103597A (de)
BR (1)	BR9714328A (de)
CA (1)	CA2279186C (de)
CO (1)	CO4920230A1 (de)
CZ (1)	CZ293173B6 (de)
DE (2)	DE69722663T2 (de)
DK (2)	DK0964849T3 (de)
DZ (1)	DZ2407A1 (de)
EA (1)	EA001803B1 (de)
ES (2)	ES2222426T3 (de)
HR (1)	HRP980045B1 (de)
HU (1)	HUP0000567A3 (de)
ID (1)	ID22223A (de)
IL (1)	IL130855A0 (de)
IS (1)	IS5099A (de)
MA (1)	MA26468A1 (de)
NO (1)	NO313279B1 (de)
NZ (1)	NZ336248A (de)
OA (1)	OA11079A (de)
PA (1)	PA8444701A1 (de)
PE (1)	PE57898A1 (de)
PL (1)	PL335052A1 (de)
PT (2)	PT1270565E (de)
SK (1)	SK283679B6 (de)
TN (1)	TNSN98017A1 (de)
TR (1)	TR199901816T2 (de)
TW (1)	TW515788B (de)
UY (1)	UY24861A1 (de)
WO (1)	WO1998032733A1 (de)
YU (1)	YU33799A (de)
ZA (1)	ZA98685B (de)

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1997
- 1997-12-29 JP JP51868798A patent/JP3573757B2/ja not_active Expired - Fee Related
- 1997-12-29 ES ES02020749T patent/ES2222426T3/es not_active Expired - Lifetime
- 1997-12-29 ID IDW990764A patent/ID22223A/id unknown
- 1997-12-29 SK SK982-99A patent/SK283679B6/sk unknown
- 1997-12-29 TR TR1999/01816T patent/TR199901816T2/xx unknown
- 1997-12-29 WO PCT/IB1997/001603 patent/WO1998032733A1/en not_active Ceased
- 1997-12-29 AT AT97947201T patent/ATE242208T1/de not_active IP Right Cessation
- 1997-12-29 HU HU0000567A patent/HUP0000567A3/hu unknown
- 1997-12-29 CA CA002279186A patent/CA2279186C/en not_active Expired - Fee Related
- 1997-12-29 US US09/341,782 patent/US6166064A/en not_active Expired - Fee Related
- 1997-12-29 PT PT02020749T patent/PT1270565E/pt unknown
- 1997-12-29 NZ NZ336248A patent/NZ336248A/xx unknown
- 1997-12-29 BR BR9714328A patent/BR9714328A/pt not_active Application Discontinuation
- 1997-12-29 PT PT97947201T patent/PT964849E/pt unknown
- 1997-12-29 CZ CZ19992575A patent/CZ293173B6/cs not_active IP Right Cessation
- 1997-12-29 CN CN97181579A patent/CN1127479C/zh not_active Expired - Fee Related
- 1997-12-29 KR KR1019997006786A patent/KR100324058B1/ko not_active Expired - Fee Related
- 1997-12-29 EA EA199900603A patent/EA001803B1/ru not_active IP Right Cessation
- 1997-12-29 DK DK97947201T patent/DK0964849T3/da active
- 1997-12-29 DE DE69722663T patent/DE69722663T2/de not_active Expired - Fee Related
- 1997-12-29 AU AU52340/98A patent/AU723895B2/en not_active Ceased
- 1997-12-29 IL IL13085597A patent/IL130855A0/xx unknown
- 1997-12-29 AT AT02020749T patent/ATE270285T1/de not_active IP Right Cessation
- 1997-12-29 EP EP97947201A patent/EP0964849B1/de not_active Expired - Lifetime
- 1997-12-29 DE DE69729762T patent/DE69729762T2/de not_active Expired - Fee Related
- 1997-12-29 YU YU33799A patent/YU33799A/sh unknown
- 1997-12-29 DK DK02020749T patent/DK1270565T3/da active
- 1997-12-29 PL PL97335052A patent/PL335052A1/xx unknown
- 1997-12-29 ES ES97947201T patent/ES2198598T3/es not_active Expired - Lifetime
1998
- 1998-01-16 PA PA19988444701A patent/PA8444701A1/es unknown
- 1998-01-20 UY UY24861A patent/UY24861A1/es unknown
- 1998-01-23 PE PE1998000051A patent/PE57898A1/es not_active Application Discontinuation
- 1998-01-26 TW TW087101087A patent/TW515788B/zh not_active IP Right Cessation
- 1998-01-27 HR HR980045A patent/HRP980045B1/xx not_active IP Right Cessation
- 1998-01-27 DZ DZ980017A patent/DZ2407A1/xx active
- 1998-01-27 AR ARP980100358A patent/AR011093A1/es not_active Application Discontinuation
- 1998-01-28 TN TNTNSN98017A patent/TNSN98017A1/fr unknown
- 1998-01-28 MA MA24947A patent/MA26468A1/fr unknown
- 1998-01-28 ZA ZA9800685A patent/ZA98685B/xx unknown
- 1998-01-29 CO CO98004326A patent/CO4920230A1/es unknown
- 1998-01-29 AP APAP/P/1998/001190A patent/AP929A/en active
1999
- 1999-06-29 IS IS5099A patent/IS5099A/is unknown
- 1999-07-22 BG BG103597A patent/BG103597A/bg unknown
- 1999-07-23 OA OA9900165A patent/OA11079A/en unknown
- 1999-07-28 NO NO19993658A patent/NO313279B1/no not_active IP Right Cessation
2000
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Also Published As

Publication number	Publication date
EA001803B1 (ru)	2001-08-27
CA2279186C (en)	2004-02-24
ES2198598T3 (es)	2004-02-01
YU33799A (sh)	2002-03-18
MA26468A1 (fr)	2004-12-20
US6433009B1 (en)	2002-08-13
CN1127479C (zh)	2003-11-12
AP929A (en)	2001-01-18
ZA98685B (en)	1999-07-29
CO4920230A1 (es)	2000-05-29
IS5099A (is)	1999-06-29
EP0964849B1 (de)	2003-06-04
ATE270285T1 (de)	2004-07-15
PT964849E (pt)	2003-08-29
BR9714328A (pt)	2000-03-21
CA2279186A1 (en)	1998-07-30
EA199900603A1 (ru)	2000-02-28
ATE242208T1 (de)	2003-06-15
AU723895B2 (en)	2000-09-07
DE69722663D1 (de)	2003-07-10
DK0964849T3 (da)	2003-08-25
PE57898A1 (es)	1999-06-11
UY24861A1 (es)	2000-09-29
US6166064A (en)	2000-12-26
CZ293173B6 (cs)	2004-02-18
BG103597A (bg)	2000-02-29
SK283679B6 (sk)	2003-11-04
TR199901816T2 (xx)	1999-11-22
EP0964849A1 (de)	1999-12-22
KR100324058B1 (ko)	2002-02-16
ES2222426T3 (es)	2005-02-01
NO313279B1 (no)	2002-09-09
PL335052A1 (en)	2000-03-27
CN1245490A (zh)	2000-02-23
WO1998032733A1 (en)	1998-07-30
DK1270565T3 (da)	2004-10-04
SK98299A3 (en)	2001-10-08
HRP980045B1 (en)	2002-10-31
ID22223A (id)	1999-09-16
KR20000070541A (ko)	2000-11-25
AU5234098A (en)	1998-08-18
NO993658D0 (no)	1999-07-28
HUP0000567A3 (en)	2002-10-28
PT1270565E (pt)	2004-09-30
TNSN98017A1 (fr)	2005-03-15
CZ257599A3 (cs)	2000-09-13
PA8444701A1 (es)	2000-05-24
JP3573757B2 (ja)	2004-10-06
IL130855A0 (en)	2001-01-28
DZ2407A1 (fr)	2003-01-04
JP2000511200A (ja)	2000-08-29
DE69729762T2 (de)	2005-07-14
DE69722663T2 (de)	2004-04-29
DE69729762D1 (de)	2004-08-05
AR011093A1 (es)	2000-08-02
NZ336248A (en)	2000-10-27
HRP980045A2 (en)	1999-06-30
NO993658L (no)	1999-09-28
HUP0000567A2 (hu)	2000-10-28
AP9801190A0 (en)	1998-03-31
TW515788B (en)	2003-01-01

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