SK9282003A3 - Pyrrole derivatives for treating cytokine mediated diseases - Google Patents

Pyrrole derivatives for treating cytokine mediated diseases Download PDF

Info

Publication number: SK9282003A3
Authority: SK; Slovakia
Prior art keywords: group; groups; substituent; compound; formula
Prior art date: 2001-01-22

Application number

SK928-2003A

Other languages

English (en)

Slovak (sk)

Inventor

Tomio Kimura

Nobuyuki Ohkawa

Akira Nakao

Takayoshi Nagasaki

Takanori Yamazaki

Original Assignee

Sankyo Co

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.)

2001-01-22

Filing date

2002-01-22

Publication date

2004-04-06

2002-01-22 Application filed by Sankyo Co filed Critical Sankyo Co

2004-04-06 Publication of SK9282003A3 publication Critical patent/SK9282003A3/sk

Links

102000004127 Cytokines Human genes 0.000 title claims abstract description 21
108090000695 Cytokines Proteins 0.000 title claims abstract description 21
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 23
201000010099 disease Diseases 0.000 title claims description 22
150000003233 pyrroles Chemical class 0.000 title description 5
230000001404 mediated effect Effects 0.000 title 1
-1 hydroxyimino Chemical group 0.000 claims abstract description 744
150000001875 compounds Chemical class 0.000 claims abstract description 490
125000001424 substituent group Chemical group 0.000 claims abstract description 454
125000000217 alkyl group Chemical group 0.000 claims abstract description 188
125000003545 alkoxy group Chemical group 0.000 claims abstract description 62
229910052757 nitrogen Inorganic materials 0.000 claims abstract description 60
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 58
125000001072 heteroaryl group Chemical group 0.000 claims abstract description 49
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 47
125000005843 halogen group Chemical group 0.000 claims abstract description 45
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 44
125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 39
238000004519 manufacturing process Methods 0.000 claims abstract description 37
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 30
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 24
125000002947 alkylene group Chemical group 0.000 claims abstract description 22
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 21
125000003342 alkenyl group Chemical group 0.000 claims abstract description 18
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 18
230000002757 inflammatory effect Effects 0.000 claims abstract description 18
125000000304 alkynyl group Chemical group 0.000 claims abstract description 17
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 17
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
125000005530 alkylenedioxy group Chemical group 0.000 claims abstract description 14
239000001257 hydrogen Substances 0.000 claims abstract description 14
125000004043 oxo group Chemical group O=* 0.000 claims abstract description 13
125000000168 pyrrolyl group Chemical group 0.000 claims abstract description 13
125000004104 aryloxy group Chemical group 0.000 claims abstract description 11
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
125000000676 alkoxyimino group Chemical group 0.000 claims abstract description 7
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
125000003341 7 membered heterocyclic group Chemical group 0.000 claims abstract description 6
229910052736 halogen Inorganic materials 0.000 claims abstract description 5
150000002367 halogens Chemical class 0.000 claims abstract description 5
125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 521
238000006243 chemical reaction Methods 0.000 claims description 209
150000002148 esters Chemical class 0.000 claims description 142
150000003839 salts Chemical class 0.000 claims description 136
238000000034 method Methods 0.000 claims description 105
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 78
241000124008 Mammalia Species 0.000 claims description 67
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 67
125000003118 aryl group Chemical group 0.000 claims description 65
125000004432 carbon atom Chemical group C* 0.000 claims description 55
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 46
239000003814 drug Substances 0.000 claims description 40
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
230000002265 prevention Effects 0.000 claims description 26
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 22
230000002401 inhibitory effect Effects 0.000 claims description 22
125000004430 oxygen atom Chemical group O* 0.000 claims description 18
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 17
230000008569 process Effects 0.000 claims description 15
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 15
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
125000005842 heteroatom Chemical group 0.000 claims description 14
229920006395 saturated elastomer Polymers 0.000 claims description 13
125000004434 sulfur atom Chemical group 0.000 claims description 13
JJKFPCYYCXXLKP-UHFFFAOYSA-N 4-pyrrol-1-ylpyridine Chemical compound C1=CC=CN1C1=CC=NC=C1 JJKFPCYYCXXLKP-UHFFFAOYSA-N 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000004076 pyridyl group Chemical group 0.000 claims description 12
125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 12
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
125000004122 cyclic group Chemical group 0.000 claims description 11
201000008482 osteoarthritis Diseases 0.000 claims description 11
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
230000001684 chronic effect Effects 0.000 claims description 10
208000001132 Osteoporosis Diseases 0.000 claims description 9
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 9
229910052760 oxygen Inorganic materials 0.000 claims description 9
239000001301 oxygen Substances 0.000 claims description 9
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 9
238000006297 dehydration reaction Methods 0.000 claims description 8
208000027866 inflammatory disease Diseases 0.000 claims description 8
239000011593 sulfur Chemical group 0.000 claims description 8
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
125000001624 naphthyl group Chemical group 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 6
125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 6
208000024827 Alzheimer disease Diseases 0.000 claims description 6
208000006386 Bone Resorption Diseases 0.000 claims description 6
206010009900 Colitis ulcerative Diseases 0.000 claims description 6
206010028980 Neoplasm Diseases 0.000 claims description 6
201000004681 Psoriasis Diseases 0.000 claims description 6
206010040047 Sepsis Diseases 0.000 claims description 6
201000006704 Ulcerative Colitis Diseases 0.000 claims description 6
125000001118 alkylidene group Chemical group 0.000 claims description 6
208000026935 allergic disease Diseases 0.000 claims description 6
208000006673 asthma Diseases 0.000 claims description 6
230000024279 bone resorption Effects 0.000 claims description 6
201000011510 cancer Diseases 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 6
208000006454 hepatitis Diseases 0.000 claims description 6
231100000283 hepatitis Toxicity 0.000 claims description 6
201000008383 nephritis Diseases 0.000 claims description 6
208000013223 septicemia Diseases 0.000 claims description 6
125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims description 5
206010037660 Pyrexia Diseases 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
206010012601 diabetes mellitus Diseases 0.000 claims description 5
230000027950 fever generation Effects 0.000 claims description 5
208000031225 myocardial ischemia Diseases 0.000 claims description 5
201000000596 systemic lupus erythematosus Diseases 0.000 claims description 5
230000003612 virological effect Effects 0.000 claims description 5
206010003210 Arteriosclerosis Diseases 0.000 claims description 4
208000011775 arteriosclerosis disease Diseases 0.000 claims description 4
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
238000005828 desilylation reaction Methods 0.000 claims description 4
LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 4
239000003085 diluting agent Substances 0.000 claims description 3
125000001153 fluoro group Chemical group F* 0.000 claims description 3
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 3
125000001422 pyrrolinyl group Chemical group 0.000 claims description 3
208000011231 Crohn disease Diseases 0.000 claims description 2
125000002029 aromatic hydrocarbon group Chemical group 0.000 claims description 2
230000000269 nucleophilic effect Effects 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
125000006413 ring segment Chemical group 0.000 claims description 2
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical group NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims 6
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical group NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 4
RQEUFEKYXDPUSK-UHFFFAOYSA-N 1-phenylethylamine Chemical group CC(N)C1=CC=CC=C1 RQEUFEKYXDPUSK-UHFFFAOYSA-N 0.000 claims 3
GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical group CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 claims 3
238000005266 casting Methods 0.000 claims 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 2
150000002641 lithium Chemical class 0.000 claims 2
125000003282 alkyl amino group Chemical group 0.000 claims 1
206010003246 arthritis Diseases 0.000 claims 1
208000029078 coronary artery disease Diseases 0.000 claims 1
230000018044 dehydration Effects 0.000 claims 1
125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
125000004429 atom Chemical group 0.000 abstract description 6
230000000694 effects Effects 0.000 abstract description 5
125000004438 haloalkoxy group Chemical group 0.000 abstract 1
125000000547 substituted alkyl group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 234
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 126
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 97
239000002904 solvent Substances 0.000 description 83
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 81
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 77
239000011541 reaction mixture Substances 0.000 description 76
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 70
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 68
239000000243 solution Substances 0.000 description 66
238000010898 silica gel chromatography Methods 0.000 description 65
239000000843 powder Substances 0.000 description 63
230000002829 reductive effect Effects 0.000 description 60
ZMANZCXQSJIPKH-UHFFFAOYSA-N triethylamine Natural products CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 56
238000002844 melting Methods 0.000 description 54
230000008018 melting Effects 0.000 description 54
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 49
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 41
239000003921 oil Substances 0.000 description 40
235000019198 oils Nutrition 0.000 description 40
239000000203 mixture Substances 0.000 description 39
235000019441 ethanol Nutrition 0.000 description 37
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 35
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 33
239000002585 base Substances 0.000 description 33
239000002253 acid Substances 0.000 description 32
239000000376 reactant Substances 0.000 description 31
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 29
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
239000000284 extract Substances 0.000 description 27
125000006239 protecting group Chemical group 0.000 description 27
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 26
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 25
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 22
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 20
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
239000003795 chemical substances by application Substances 0.000 description 20
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 19
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 19
239000007858 starting material Substances 0.000 description 18
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 18
238000006460 hydrolysis reaction Methods 0.000 description 16
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 15
150000002170 ethers Chemical class 0.000 description 15
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 14
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 14
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
125000005129 aryl carbonyl group Chemical group 0.000 description 14
239000003153 chemical reaction reagent Substances 0.000 description 14
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
150000001412 amines Chemical class 0.000 description 13
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 12
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
150000001298 alcohols Chemical class 0.000 description 12
238000001816 cooling Methods 0.000 description 12
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 12
239000000706 filtrate Substances 0.000 description 11
238000003756 stirring Methods 0.000 description 11
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 10
235000011054 acetic acid Nutrition 0.000 description 10
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 10
238000004440 column chromatography Methods 0.000 description 10
238000006114 decarboxylation reaction Methods 0.000 description 10
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
229910000029 sodium carbonate Inorganic materials 0.000 description 10
239000008096 xylene Substances 0.000 description 10
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 9
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 9
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 9
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 9
150000008282 halocarbons Chemical class 0.000 description 9
230000007062 hydrolysis Effects 0.000 description 9
231100000989 no adverse effect Toxicity 0.000 description 9
239000002798 polar solvent Substances 0.000 description 9
239000000047 product Substances 0.000 description 9
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 9
238000003786 synthesis reaction Methods 0.000 description 9
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AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
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229910052783 alkali metal Inorganic materials 0.000 description 8
229910000102 alkali metal hydride Inorganic materials 0.000 description 8
150000008046 alkali metal hydrides Chemical class 0.000 description 8
150000008044 alkali metal hydroxides Chemical class 0.000 description 8
150000001408 amides Chemical class 0.000 description 8
150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
239000012230 colorless oil Substances 0.000 description 8
229910000103 lithium hydride Inorganic materials 0.000 description 8
150000002825 nitriles Chemical class 0.000 description 8
229910000027 potassium carbonate Inorganic materials 0.000 description 8
239000012312 sodium hydride Substances 0.000 description 8
229910000104 sodium hydride Inorganic materials 0.000 description 8
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 8
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 7
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
125000002252 acyl group Chemical group 0.000 description 7
229910000288 alkali metal carbonate Inorganic materials 0.000 description 7
150000008041 alkali metal carbonates Chemical class 0.000 description 7
125000004453 alkoxycarbonyl group Chemical group 0.000 description 7
239000012280 lithium aluminium hydride Substances 0.000 description 7
230000004060 metabolic process Effects 0.000 description 7
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 7
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
125000001931 aliphatic group Chemical group 0.000 description 6
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
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229920001592 potato starch Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical class CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
150000003180 prostaglandins Chemical class 0.000 description 1
235000019423 pullulan Nutrition 0.000 description 1
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
NGHMEZWZOZEZOH-UHFFFAOYSA-N silicic acid;hydrate Chemical compound O.O[Si](O)(O)O NGHMEZWZOZEZOH-UHFFFAOYSA-N 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
239000004299 sodium benzoate Substances 0.000 description 1
235000010234 sodium benzoate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229920003109 sodium starch glycolate Polymers 0.000 description 1
239000008109 sodium starch glycolate Substances 0.000 description 1
229940079832 sodium starch glycolate Drugs 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
RBBWNXJFTBCLKT-UHFFFAOYSA-M sodium;ethanethioate Chemical compound [Na+].CC([S-])=O RBBWNXJFTBCLKT-UHFFFAOYSA-M 0.000 description 1
239000011949 solid catalyst Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
229940086735 succinate Drugs 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
NCEXYHBECQHGNR-QZQOTICOSA-N sulfasalazine Chemical compound C1=C(O)C(C(=O)O)=CC(\N=N\C=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-QZQOTICOSA-N 0.000 description 1
229960001940 sulfasalazine Drugs 0.000 description 1
NCEXYHBECQHGNR-UHFFFAOYSA-N sulfasalazine Natural products C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000005942 tetrahydropyridyl group Chemical group 0.000 description 1
125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
229940033663 thimerosal Drugs 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
230000014616 translation Effects 0.000 description 1
LHJCZOXMCGQVDQ-UHFFFAOYSA-N tri(propan-2-yl)silyl trifluoromethanesulfonate Chemical compound CC(C)[Si](C(C)C)(C(C)C)OS(=O)(=O)C(F)(F)F LHJCZOXMCGQVDQ-UHFFFAOYSA-N 0.000 description 1
ISEIIPDWJVGTQS-UHFFFAOYSA-N tributylsilicon Chemical compound CCCC[Si](CCCC)CCCC ISEIIPDWJVGTQS-UHFFFAOYSA-N 0.000 description 1
125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
125000002827 triflate group Chemical class FC(S(=O)(=O)O*)(F)F 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
ZHOVAWFVVBWEGQ-UHFFFAOYSA-N tripropylsilane Chemical compound CCC[SiH](CCC)CCC ZHOVAWFVVBWEGQ-UHFFFAOYSA-N 0.000 description 1
125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000012873 virucide Substances 0.000 description 1
230000008673 vomiting Effects 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- 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]
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Rheumatology (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pain & Pain Management (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SK928-2003A 2001-01-22 2002-01-22 Pyrrole derivatives for treating cytokine mediated diseases SK9282003A3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
JP2001013817		2001-01-22
US27500501P	2001-03-12	2001-03-12
PCT/IB2002/000176 WO2002057264A1 (en)	2001-01-22	2002-01-22	Pyrrole derivates for treating cytokine mediated diseases

Publications (1)

Publication Number	Publication Date
SK9282003A3 true SK9282003A3 (en)	2004-04-06

Family

ID=26608097

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK928-2003A SK9282003A3 (en)	2001-01-22	2002-01-22	Pyrrole derivatives for treating cytokine mediated diseases

Country Status (21)

Country	Link
EP (1)	EP1377577B1 (cs)
KR (1)	KR20030076619A (cs)
CN (1)	CN100371336C (cs)
AR (1)	AR032511A1 (cs)
AT (1)	ATE329915T1 (cs)
BR (1)	BR0206650A (cs)
CA (1)	CA2435692A1 (cs)
CZ (1)	CZ20031949A3 (cs)
DE (1)	DE60212357T2 (cs)
EG (1)	EG23054A (cs)
ES (1)	ES2266500T3 (cs)
HU (1)	HUP0302807A2 (cs)
IL (1)	IL156861A0 (cs)
MX (1)	MXPA03006515A (cs)
NO (1)	NO20033290L (cs)
NZ (1)	NZ527099A (cs)
PE (1)	PE20030197A1 (cs)
PL (1)	PL362896A1 (cs)
RU (1)	RU2003122364A (cs)
SK (1)	SK9282003A3 (cs)
WO (1)	WO2002057264A1 (cs)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
WO2003015781A1 (en) *	2001-08-15	2003-02-27	Sankyo Company, Limited	Novel antidiabetic pharmaceutical compositions
EP1541571A4 (en) *	2002-07-19	2008-12-03	Sankyo Co	BICYCLIC, UNSATURATED TERTIARY AMINE COMPOUND
WO2006066361A1 (en)	2004-12-24	2006-06-29	The University Of Queensland	Method of treatment or prophylaxis
US20130131007A1 (en)	2005-09-07	2013-05-23	Bebaas, Inc.	Vitamin b12 compositions
CA2866540A1 (en)	2006-03-20	2007-09-27	Spinifex Pharmaceuticals Pty Ltd.	Method of treatment or prophylaxis of inflammatory pain

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5837719A (en) *	1995-08-10	1998-11-17	Merck & Co., Inc.	2,5-substituted aryl pyrroles, compositions containing such compounds and methods of use
US5792778A (en) *	1995-08-10	1998-08-11	Merck & Co., Inc.	2-substituted aryl pyrroles, compositions containing such compounds and methods of use
WO1997005878A1 (en) *	1995-08-10	1997-02-20	Merck & Co., Inc.	2,5-substituted aryl pyrroles, compositions containing such compounds and methods of use
IL137365A0 (en) *	1999-07-21	2001-07-24	Sankyo Co	Heteroaryl-substituted pyrrole derivatives, processes for the preparation thereof and pharmaceutical compositions containing the same

2002
- 2002-01-20 EG EG20020068A patent/EG23054A/xx active
- 2002-01-22 DE DE60212357T patent/DE60212357T2/de not_active Expired - Fee Related
- 2002-01-22 SK SK928-2003A patent/SK9282003A3/sk not_active Application Discontinuation
- 2002-01-22 CZ CZ20031949A patent/CZ20031949A3/cs unknown
- 2002-01-22 AT AT02732180T patent/ATE329915T1/de not_active IP Right Cessation
- 2002-01-22 HU HU0302807A patent/HUP0302807A2/hu unknown
- 2002-01-22 MX MXPA03006515A patent/MXPA03006515A/es unknown
- 2002-01-22 CA CA002435692A patent/CA2435692A1/en not_active Abandoned
- 2002-01-22 WO PCT/IB2002/000176 patent/WO2002057264A1/en not_active Ceased
- 2002-01-22 EP EP02732180A patent/EP1377577B1/en not_active Expired - Lifetime
- 2002-01-22 RU RU2003122364/04A patent/RU2003122364A/ru unknown
- 2002-01-22 NZ NZ527099A patent/NZ527099A/en unknown
- 2002-01-22 BR BR0206650-5A patent/BR0206650A/pt not_active IP Right Cessation
- 2002-01-22 KR KR10-2003-7009619A patent/KR20030076619A/ko not_active Ceased
- 2002-01-22 PE PE2002000046A patent/PE20030197A1/es not_active Application Discontinuation
- 2002-01-22 AR ARP020100212A patent/AR032511A1/es unknown
- 2002-01-22 ES ES02732180T patent/ES2266500T3/es not_active Expired - Lifetime
- 2002-01-22 CN CNB028069781A patent/CN100371336C/zh not_active Expired - Fee Related
- 2002-01-22 IL IL15686102A patent/IL156861A0/xx unknown
- 2002-01-22 PL PL02362896A patent/PL362896A1/xx not_active Application Discontinuation
2003
- 2003-07-21 NO NO20033290A patent/NO20033290L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
CA2435692A1 (en)	2002-07-25
BR0206650A (pt)	2004-02-25
WO2002057264A1 (en)	2002-07-25
NO20033290D0 (no)	2003-07-21
ATE329915T1 (de)	2006-07-15
CN1553911A (zh)	2004-12-08
CN100371336C (zh)	2008-02-27
IL156861A0 (en)	2004-02-08
ES2266500T3 (es)	2007-03-01
DE60212357D1 (de)	2006-07-27
NO20033290L (no)	2003-09-11
PL362896A1 (en)	2004-11-02
PE20030197A1 (es)	2003-03-12
MXPA03006515A (es)	2003-10-15
EP1377577B1 (en)	2006-06-14
AR032511A1 (es)	2003-11-12
HUP0302807A2 (hu)	2003-12-29
DE60212357T2 (de)	2007-05-31
RU2003122364A (ru)	2005-03-27
KR20030076619A (ko)	2003-09-26
EP1377577A1 (en)	2004-01-07
NZ527099A (en)	2004-09-24
CZ20031949A3 (cs)	2003-12-17
EG23054A (en)	2004-02-29

Legal Events

Date	Code	Title	Description
2010-12-07	FC9A	Refused patent application

Publication	Publication Date	Title
KR20070026708A (ko)	2007-03-08	헤테로아릴 치환 피롤 유도체, 그의 제조방법 및 그의치료적 용도
US7122666B2 (en)	2006-10-17	Heteroaryl-substituted pyrrole derivatives, their preparation and their therapeutic uses
JP2002284779A (ja)	2002-10-03	ヘテロアリール置換ピロール誘導体を含有する医薬
EP1377577B1 (en)	2006-06-14	Pyrrole derivates for treating cytokine mediated diseases
JP2003261566A (ja)	2003-09-19	キノリジンを含有する医薬
JP2003128551A (ja)	2003-05-08	新規抗糖尿病医薬組成物
AU2007205452B2 (en)	2012-04-12	Pyrrolopyridazinone compound
JP2002284783A (ja)	2002-10-03	二環性アミノ基置換ピロール誘導体
JP3088672B2 (ja)	2000-09-18	飽和複素環化合物
JP2001247564A (ja)	2001-09-11	ヘテロアリール置換ピロール誘導体
JP2001181187A (ja)	2001-07-03	５員ヘテロアリール化合物を含有する組成物
EP1352906A1 (en)	2003-10-15	Compositions for prevention or treatment of hepatopathy
JP2000080094A (ja)	2000-03-21	５員ヘテロアリ―ル化合物
CZ20002629A3 (cs)	2001-03-14	Heteroarylem substituované deriváty pyrrolu, jejich příprava a terapeutické použití
JP2002284681A (ja)	2002-10-03	肝障害を予防又は治療するための組成物
JP2002284782A (ja)	2002-10-03	二環性アミノ基置換化合物
JP2001072662A (ja)	2001-03-21	インドリン又はテトラヒドロキノリン誘導体
JPH10152478A (ja)	1998-06-09	飽和複素環化合物
HK1033945A (en)	2001-10-05	Heteroaryl-substituted pyrrole derivatives, their preparation and their therapeutic uses
JP2003212853A (ja)	2003-07-30	４−オキソキノリン誘導体