HRP970378A2 - Pyridylpyrrole compounds - Google Patents

Pyridylpyrrole compounds Download PDF

Info

Publication number: HRP970378A2
Authority: HR; Croatia
Prior art keywords: pyridyl; alkyl; halo; pyrrole; methyl
Prior art date: 1996-07-11

Application number

HRPCT/IB96/00671A

Other languages

English (en)

Croatian (hr)

Inventor

Minoru Sakakibara

Original Assignee

Minoru Sakakibara

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.)

1996-07-11

Filing date

1997-07-11

Publication date

1998-08-31

1997-07-11 Application filed by Minoru Sakakibara filed Critical Minoru Sakakibara

1998-08-31 Publication of HRP970378A2 publication Critical patent/HRP970378A2/hr

Links

150000001875 compounds Chemical class 0.000 title claims description 160
-1 nitro, hydroxy, amino Chemical class 0.000 claims description 131
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 102
238000000034 method Methods 0.000 claims description 100
125000005843 halogen group Chemical group 0.000 claims description 81
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 71
229910052739 hydrogen Inorganic materials 0.000 claims description 65
239000001257 hydrogen Substances 0.000 claims description 65
150000002431 hydrogen Chemical class 0.000 claims description 52
125000000217 alkyl group Chemical group 0.000 claims description 48
125000004076 pyridyl group Chemical group 0.000 claims description 48
125000000168 pyrrolyl group Chemical group 0.000 claims description 45
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 36
125000001544 thienyl group Chemical group 0.000 claims description 36
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 32
125000002541 furyl group Chemical group 0.000 claims description 32
125000001624 naphthyl group Chemical group 0.000 claims description 32
238000006243 chemical reaction Methods 0.000 claims description 28
125000005493 quinolyl group Chemical group 0.000 claims description 28
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 25
201000010099 disease Diseases 0.000 claims description 22
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
239000000825 pharmaceutical preparation Substances 0.000 claims description 21
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 18
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 17
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 16
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
102000004127 Cytokines Human genes 0.000 claims description 15
108090000695 Cytokines Proteins 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 14
CFDCGXXHXUZSNP-UHFFFAOYSA-N 1-(4-methyl-2,5-dipyridin-4-yl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 CFDCGXXHXUZSNP-UHFFFAOYSA-N 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 12
125000000951 phenoxy group Chemical class [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 12
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 11
125000001041 indolyl group Chemical group 0.000 claims description 11
VGMYYTPVOVGRKN-UHFFFAOYSA-N 1-(2,4-dimethyl-5-pyridin-4-yl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C1=C(C)NC(C=2C=CN=CC=2)=C1C VGMYYTPVOVGRKN-UHFFFAOYSA-N 0.000 claims description 10
208000022559 Inflammatory bowel disease Diseases 0.000 claims description 9
239000012442 inert solvent Substances 0.000 claims description 9
206010061218 Inflammation Diseases 0.000 claims description 8
206010040070 Septic Shock Diseases 0.000 claims description 8
125000004414 alkyl thio group Chemical group 0.000 claims description 8
125000002947 alkylene group Chemical group 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 8
229910002091 carbon monoxide Inorganic materials 0.000 claims description 8
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 8
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 8
125000002883 imidazolyl group Chemical group 0.000 claims description 8
230000004054 inflammatory process Effects 0.000 claims description 8
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 8
125000002971 oxazolyl group Chemical group 0.000 claims description 8
125000003356 phenylsulfanyl group Chemical class [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
125000003831 tetrazolyl group Chemical group 0.000 claims description 8
125000000335 thiazolyl group Chemical group 0.000 claims description 8
125000001425 triazolyl group Chemical group 0.000 claims description 8
CQTUQSPZQSUMQF-UHFFFAOYSA-N 3,7,7-trimethyl-2-pyridin-4-yl-5,6-dihydro-1h-indol-4-one Chemical compound N1C(C(CCC2=O)(C)C)=C2C(C)=C1C1=CC=NC=C1 CQTUQSPZQSUMQF-UHFFFAOYSA-N 0.000 claims description 7
206010003246 arthritis Diseases 0.000 claims description 7
125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 6
MBTIRJCWEUGLQN-UHFFFAOYSA-N 1-(4-methyl-2-phenyl-5-pyridin-4-yl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=CC=C1 MBTIRJCWEUGLQN-UHFFFAOYSA-N 0.000 claims description 6
OAQHMDXYUNLJAW-UHFFFAOYSA-N 3-methyl-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound N1C=2CCCC(=O)C=2C(C)=C1C1=CC=NC=C1 OAQHMDXYUNLJAW-UHFFFAOYSA-N 0.000 claims description 6
206010006895 Cachexia Diseases 0.000 claims description 6
201000005569 Gout Diseases 0.000 claims description 6
206010040047 Sepsis Diseases 0.000 claims description 6
125000003118 aryl group Chemical group 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
ZZVBBGRLNWHGKI-UHFFFAOYSA-N 1-(4-ethyl-2,5-dipyridin-4-yl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C=1C(CC)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 ZZVBBGRLNWHGKI-UHFFFAOYSA-N 0.000 claims description 5
VBRZIZQAEKDYQT-UHFFFAOYSA-N 1-(4-methyl-2-piperidin-1-yl-5-pyridin-4-yl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1N1CCCCC1 VBRZIZQAEKDYQT-UHFFFAOYSA-N 0.000 claims description 5
OIQDPAUDWHKBHK-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)-4-methyl-5-pyridin-4-yl-1h-pyrrol-3-yl]ethanone Chemical compound CC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=C(F)C=C1 OIQDPAUDWHKBHK-UHFFFAOYSA-N 0.000 claims description 5
GRPGEHJNRYQOKP-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)-4-methyl-5-pyridin-4-yl-1h-pyrrol-3-yl]ethanone Chemical compound C1=CC(OC)=CC=C1C1=C(C(C)=O)C(C)=C(C=2C=CN=CC=2)N1 GRPGEHJNRYQOKP-UHFFFAOYSA-N 0.000 claims description 5
UCFDLEPYTFZWAA-UHFFFAOYSA-N 3,6,6-trimethyl-2-pyridin-4-yl-5,7-dihydro-1h-indol-4-one Chemical compound N1C=2CC(C)(C)CC(=O)C=2C(C)=C1C1=CC=NC=C1 UCFDLEPYTFZWAA-UHFFFAOYSA-N 0.000 claims description 5
ABERWOGDIPSMRX-UHFFFAOYSA-N 3,6-dimethyl-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound CC=1C=2C(=O)CC(C)CC=2NC=1C1=CC=NC=C1 ABERWOGDIPSMRX-UHFFFAOYSA-N 0.000 claims description 5
208000030507 AIDS Diseases 0.000 claims description 5
125000000815 N-oxide group Chemical group 0.000 claims description 5
201000004681 Psoriasis Diseases 0.000 claims description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
208000027866 inflammatory disease Diseases 0.000 claims description 5
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
VSHSBDXBPIMNIW-UHFFFAOYSA-N methyl 4-methyl-2,5-dipyridin-4-yl-1h-pyrrole-3-carboxylate Chemical compound COC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 VSHSBDXBPIMNIW-UHFFFAOYSA-N 0.000 claims description 5
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
210000000056 organ Anatomy 0.000 claims description 5
230000036303 septic shock Effects 0.000 claims description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
125000004747 1,1-dimethylethoxycarbonyl group Chemical group CC(C)(OC(=O)*)C 0.000 claims description 4
VZEWYUNAGKOSEB-UHFFFAOYSA-N 1-[2,5-dipyridin-4-yl-4-(trifluoromethyl)-1h-pyrrol-3-yl]ethanone Chemical compound FC(F)(F)C=1C(C(=O)C)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 VZEWYUNAGKOSEB-UHFFFAOYSA-N 0.000 claims description 4
PISUAZYYXFTULY-UHFFFAOYSA-N 1-[2-(2-fluorophenyl)-4-methyl-5-pyridin-4-yl-1h-pyrrol-3-yl]ethanone Chemical compound CC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=CC=C1F PISUAZYYXFTULY-UHFFFAOYSA-N 0.000 claims description 4
MJHQNOKCZUFOOY-UHFFFAOYSA-N 1-[2-(3-chloro-4-fluorophenyl)-4-methyl-5-pyridin-4-yl-1h-pyrrol-3-yl]ethanone Chemical compound CC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=C(F)C(Cl)=C1 MJHQNOKCZUFOOY-UHFFFAOYSA-N 0.000 claims description 4
MHTAJIUSPWVIQC-UHFFFAOYSA-N 1-[4-methyl-2-(4-phenylpiperazin-1-yl)-5-pyridin-4-yl-1h-pyrrol-3-yl]ethanone Chemical compound CC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1N(CC1)CCN1C1=CC=CC=C1 MHTAJIUSPWVIQC-UHFFFAOYSA-N 0.000 claims description 4
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 4
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 4
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
208000024172 Cardiovascular disease Diseases 0.000 claims description 4
208000011231 Crohn disease Diseases 0.000 claims description 4
206010052779 Transplant rejections Diseases 0.000 claims description 4
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
125000003282 alkyl amino group Chemical group 0.000 claims description 4
208000006673 asthma Diseases 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 4
125000004744 butyloxycarbonyl group Chemical group 0.000 claims description 4
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 4
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000006501 nitrophenyl group Chemical group 0.000 claims description 4
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 4
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 4
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 4
125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000004742 propyloxycarbonyl group Chemical group 0.000 claims description 4
206010039083 rhinitis Diseases 0.000 claims description 4
125000006413 ring segment Chemical group 0.000 claims description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
ADHKPIAZBHTKOE-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)-4-methyl-5-pyridin-4-yl-1h-pyrrol-3-yl]ethanone Chemical compound CC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=C(Cl)C=C1 ADHKPIAZBHTKOE-UHFFFAOYSA-N 0.000 claims description 3
208000007536 Thrombosis Diseases 0.000 claims description 3
208000036142 Viral infection Diseases 0.000 claims description 3
125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
230000009385 viral infection Effects 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 8
102100025580 Calmodulin-1 Human genes 0.000 claims 2
101001091610 Homo sapiens Krev interaction trapped protein 1 Proteins 0.000 claims 2
229960005486 vaccine Drugs 0.000 claims 2
230000000116 mitigating effect Effects 0.000 claims 1
MSTPNDZQVGSTET-UHFFFAOYSA-M sodium;2-anilino-6-sulfanylidene-1h-1,3,5-triazine-4-thiolate Chemical compound [Na+].N1C(=S)N=C([S-])N=C1NC1=CC=CC=C1 MSTPNDZQVGSTET-UHFFFAOYSA-M 0.000 claims 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 130
238000005160 1H NMR spectroscopy Methods 0.000 description 122
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 90
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 79
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 68
239000000203 mixture Substances 0.000 description 68
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 39
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
210000004027 cell Anatomy 0.000 description 34
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 30
235000019439 ethyl acetate Nutrition 0.000 description 29
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 26
239000012044 organic layer Substances 0.000 description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
238000001816 cooling Methods 0.000 description 24
239000000243 solution Substances 0.000 description 24
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 22
238000003818 flash chromatography Methods 0.000 description 22
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
108060008682 Tumor Necrosis Factor Proteins 0.000 description 21
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 20
239000000047 product Substances 0.000 description 20
239000007787 solid Substances 0.000 description 20
102000003390 tumor necrosis factor Human genes 0.000 description 20
NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 19
238000010992 reflux Methods 0.000 description 19
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 15
239000012267 brine Substances 0.000 description 15
229920006395 saturated elastomer Polymers 0.000 description 15
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 14
102000016289 Cell Adhesion Molecules Human genes 0.000 description 13
108010067225 Cell Adhesion Molecules Proteins 0.000 description 13
238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 13
229910052943 magnesium sulfate Inorganic materials 0.000 description 13
235000019341 magnesium sulphate Nutrition 0.000 description 13
102000000589 Interleukin-1 Human genes 0.000 description 12
108010002352 Interleukin-1 Proteins 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 12
QLULGIRFKAWHOJ-UHFFFAOYSA-N pyridin-4-ylboronic acid Chemical compound OB(O)C1=CC=NC=C1 QLULGIRFKAWHOJ-UHFFFAOYSA-N 0.000 description 12
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 11
239000000706 filtrate Substances 0.000 description 11
VGZCKCJMYREIKA-UHFFFAOYSA-N 1-(2,4-dimethyl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C=1C(C)=CNC=1C VGZCKCJMYREIKA-UHFFFAOYSA-N 0.000 description 10
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 10
230000015572 biosynthetic process Effects 0.000 description 10
230000005764 inhibitory process Effects 0.000 description 10
BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
229910000104 sodium hydride Inorganic materials 0.000 description 9
238000003756 stirring Methods 0.000 description 9
239000003039 volatile agent Substances 0.000 description 9
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
HJVPKTCQFGHJQW-UHFFFAOYSA-N 1-(5-bromo-2,4-dimethyl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C1=C(C)NC(Br)=C1C HJVPKTCQFGHJQW-UHFFFAOYSA-N 0.000 description 8
239000003054 catalyst Substances 0.000 description 8
238000001704 evaporation Methods 0.000 description 8
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102000057041 human TNF Human genes 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229960000890 hydrocortisone Drugs 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
208000026278 immune system disease Diseases 0.000 description 1
230000007365 immunoregulation Effects 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
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238000001764 infiltration Methods 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
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239000003112 inhibitor Substances 0.000 description 1
238000010255 intramuscular injection Methods 0.000 description 1
239000007927 intramuscular injection Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000002346 iodo group Chemical group I* 0.000 description 1
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239000007788 liquid Substances 0.000 description 1
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VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
230000036210 malignancy Effects 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
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AUTCCPQKLPMHDN-ONEGZZNKSA-N methyl (e)-3-methoxyprop-2-enoate Chemical compound CO\C=C\C(=O)OC AUTCCPQKLPMHDN-ONEGZZNKSA-N 0.000 description 1
XQUFLSYLEHOANN-UHFFFAOYSA-N methyl 4-(methoxymethyl)-2,5-dipyridin-4-yl-1h-pyrrole-3-carboxylate Chemical compound COCC=1C(C(=O)OC)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 XQUFLSYLEHOANN-UHFFFAOYSA-N 0.000 description 1
OPURNNHYTATPKM-UHFFFAOYSA-N methyl 5-methoxy-3-oxopentanoate Chemical compound COCCC(=O)CC(=O)OC OPURNNHYTATPKM-UHFFFAOYSA-N 0.000 description 1
SMQSMQUBQPWGAO-UHFFFAOYSA-N methylsulfonyl acetate Chemical compound CC(=O)OS(C)(=O)=O SMQSMQUBQPWGAO-UHFFFAOYSA-N 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000005087 mononuclear cell Anatomy 0.000 description 1
230000003387 muscular Effects 0.000 description 1
IZUQZLGWRCYWCB-UHFFFAOYSA-N n-[(4-methoxyphenyl)methylideneamino]aniline Chemical compound C1=CC(OC)=CC=C1C=NNC1=CC=CC=C1 IZUQZLGWRCYWCB-UHFFFAOYSA-N 0.000 description 1
IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
USPBRALCUPNARB-UHFFFAOYSA-N n-methoxy-2-(4-methyl-2,5-dipyridin-4-yl-1h-pyrrol-3-yl)ethanimine;hydrochloride Chemical compound Cl.CON=CCC=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 USPBRALCUPNARB-UHFFFAOYSA-N 0.000 description 1
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
238000010534 nucleophilic substitution reaction Methods 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000008183 oral pharmaceutical preparation Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
210000003819 peripheral blood mononuclear cell Anatomy 0.000 description 1
108040007629 peroxidase activity proteins Proteins 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
230000004962 physiological condition Effects 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
230000008569 process Effects 0.000 description 1
UIAVBVHIBKBUQQ-UHFFFAOYSA-N propan-2-yl 4-methyl-2,5-dipyridin-4-yl-1h-pyrrole-3-carboxylate Chemical compound CC(C)OC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 UIAVBVHIBKBUQQ-UHFFFAOYSA-N 0.000 description 1
238000001243 protein synthesis Methods 0.000 description 1
201000003651 pulmonary sarcoidosis Diseases 0.000 description 1
238000011002 quantification Methods 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
WPYJKGWLDJECQD-UHFFFAOYSA-N quinoline-2-carbaldehyde Chemical class C1=CC=CC2=NC(C=O)=CC=C21 WPYJKGWLDJECQD-UHFFFAOYSA-N 0.000 description 1
208000002574 reactive arthritis Diseases 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
102000005962 receptors Human genes 0.000 description 1
108020003175 receptors Proteins 0.000 description 1
230000000241 respiratory effect Effects 0.000 description 1
230000004044 response Effects 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
201000005404 rubella Diseases 0.000 description 1
231100000241 scar Toxicity 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000011083 sodium citrates Nutrition 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
201000004595 synovitis Diseases 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
UQEPTRSRIANXOI-UHFFFAOYSA-N tert-butyl 4-methyl-2,5-dipyridin-4-yl-1h-pyrrole-3-carboxylate Chemical compound CC(C)(C)OC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 UQEPTRSRIANXOI-UHFFFAOYSA-N 0.000 description 1
CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 1
230000009772 tissue formation Effects 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
238000013518 transcription Methods 0.000 description 1
230000035897 transcription Effects 0.000 description 1
230000014616 translation Effects 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
239000012588 trypsin Substances 0.000 description 1
201000008827 tuberculosis Diseases 0.000 description 1
230000006433 tumor necrosis factor production Effects 0.000 description 1
102000003298 tumor necrosis factor receptor Human genes 0.000 description 1
210000003606 umbilical vein Anatomy 0.000 description 1
210000003556 vascular endothelial cell Anatomy 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229940102001 zinc bromide Drugs 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrrole Compounds (AREA)

HRPCT/IB96/00671A 1996-07-11 1997-07-11 Pyridylpyrrole compounds HRP970378A2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IB9600671		1996-07-11

Publications (1)

Publication Number	Publication Date
HRP970378A2 true HRP970378A2 (en)	1998-08-31

Family

ID=11004451

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HRPCT/IB96/00671A HRP970378A2 (en)	1996-07-11	1997-07-11	Pyridylpyrrole compounds

Country Status (14)

Country	Link
US (1)	US6417202B1 (id)
EP (1)	EP0912548A1 (id)
AP (1)	AP9701041A0 (id)
AR (1)	AR007828A1 (id)
AU (1)	AU3044197A (id)
BR (1)	BR9710352A (id)
CA (1)	CA2260213C (id)
HN (1)	HN1997000090A (id)
HR (1)	HRP970378A2 (id)
ID (1)	ID19476A (id)
MA (1)	MA26433A1 (id)
PA (1)	PA8432901A1 (id)
TN (1)	TNSN97119A1 (id)
WO (1)	WO1998002430A1 (id)

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US5945418A (en) *	1996-12-18	1999-08-31	Vertex Pharmaceuticals Incorporated	Inhibitors of p38
US6147080A (en) *	1996-12-18	2000-11-14	Vertex Pharmaceuticals Incorporated	Inhibitors of p38
US6608060B1 (en)	1996-12-18	2003-08-19	Vertex Pharmaceuticals Incorporated	Inhibitors of p38
PT853083E (pt) *	1997-01-06	2001-12-28	Pfizer	Composto de piridilfurano e piridiltiofeno e sua utilizacao farmaceutica
FR2771412B1 (fr) *	1997-11-26	2000-04-28	Adir	Nouveaux derives de pyrrole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent
EP1057485B1 (en) *	1998-01-14	2005-05-11	Nippon Shinyaku Co., Ltd.	Potassium channel activators
AU3953899A (en) *	1998-05-27	1999-12-13	Nippon Shinyaku Co. Ltd.	Cyclooxygenase-2 inhibitors
WO2000066124A1 (fr) *	1999-04-28	2000-11-09	Sankyo Company, Limited	Agents preventifs ou inhibiteurs destines a une hepatopathie
KR20010114267A (ko) *	1999-05-14	2001-12-31	오르토-맥네일 파마슈티칼, 인코퍼레이티드	치환된 3-피리딜-4-아릴피롤과 관련 치료방법 및 예방방법
CN1414951A (zh) *	1999-10-28	2003-04-30	基本治疗公司	药剂排出泵抑制药
GB0003154D0 (en)	2000-02-12	2000-04-05	Astrazeneca Uk Ltd	Novel compounds
GB0016453D0 (en) *	2000-07-04	2000-08-23	Hoffmann La Roche	Pyrrole derivatives
KR20030076612A (ko) *	2001-01-18	2003-09-26	상꾜 가부시키가이샤	간장해를 예방 또는 치료하기 위한 조성물
US7056917B2 (en) *	2001-04-26	2006-06-06	Daiichi Pharmaceutical Co., Ltd.	Drug efflux pump inhibitor
CA2665516A1 (en) *	2001-04-26	2002-11-07	Daiichi Pharmaceutical Co., Ltd.	Drug efflux pump inhibitor
SE0102617D0 (sv)	2001-07-25	2001-07-25	Astrazeneca Ab	Novel compounds
SE0102616D0 (sv)	2001-07-25	2001-07-25	Astrazeneca Ab	Novel compounds
DE60207273T2 (de)	2001-08-30	2006-07-20	F. Hoffmann-La Roche Ag	Aminopyrrolverbindungen als entzündungshemmende Wirkstoffe
AU2003297431A1 (en) *	2002-12-20	2004-07-22	Pharmacia Corporation	Mitogen activated protein kinase-activated protein kinase-2 inhibiting compounds
SE0300091D0 (sv)	2003-01-15	2003-01-15	Astrazeneca Ab	Novel compounds
SE0300092D0 (sv)	2003-01-15	2003-01-15	Astrazeneca Ab	Novel compounds
US20050043346A1 (en) *	2003-08-08	2005-02-24	Pharmacia Italia S.P.A.	Pyridylpyrrole derivatives active as kinase inhibitors
EP1729776A1 (en) *	2004-02-20	2006-12-13	AstraZeneca AB	Pyrrole derivatives as gonadotropin releasing hormone (gnrh) antagonists
BRPI0620079A2 (pt) *	2005-12-19	2011-11-01	Syngenta Ltd	compostos heterocìclicos aromáticos substituìdos como fungicidas
US7618982B2 (en) *	2005-12-19	2009-11-17	Nerviano Medical Sciences S.R.L.	Heteroarylpyrrolopyridinones active as kinase inhibitors
UA94097C2 (ru) *	2006-03-27	2011-04-11	НЕРВИАНО МЕДИКАЛ САЙЕНСИЗ С.р.л.	Пиридил- и пиримидинилзамещенные производной пиррола, тиофена и фурана как ингибиторы киназ
EP2069333A1 (en)	2006-09-21	2009-06-17	Novartis Ag	Pyrrole derivatives useful for the treatment of cytokine-mediated diseases
CN104379573A (zh) *	2012-04-20	2015-02-25	艾伯维公司	异吲哚酮衍生物
EP2838881B1 (en)	2012-04-20	2018-08-08	AbbVie Inc.	Isoindolone derivatives
WO2014165127A1 (en) *	2013-03-12	2014-10-09	Abbvie Inc.	Pyrrole amide inhibitors
ES2708211T3 (es)	2014-06-17	2019-04-09	Bayer Pharma AG	3-amino-1,5,6,7-tetrahidro-4H-indol-4-onas
JP2019504826A (ja) *	2015-12-16	2019-02-21	バイエルファーマアクチエンゲゼルシャフト	ヘテロ−１，５，６，７−テトラヒドロ−４ｈ−インドール−４−オン類

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DE69627006T2 (de) *	1995-08-10	2004-01-15	Merck & Co Inc	2-substituierte aryl-pyrrolen, zusammensetzungen solche verbindungen enthaltend und deren verwendung
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WO1997016442A1 (en)	1995-10-31	1997-05-09	Merck & Co., Inc.	Substituted pyridyl pyrroles, compositions containing such compounds and methods of use
WO1997016441A1 (en) *	1995-10-31	1997-05-09	Merck & Co., Inc.	Substituted aryl pyrroles, compositions containing such compounds and methods of use
AU7529096A (en)	1995-10-31	1997-05-22	Merck & Co., Inc.	Substituted aryl pyrroles, compositions containing such compounds and methods of use
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1997
- 1997-06-16 CA CA002260213A patent/CA2260213C/en not_active Expired - Fee Related
- 1997-06-16 WO PCT/IB1997/000703 patent/WO1998002430A1/en not_active Ceased
- 1997-06-16 BR BR9710352A patent/BR9710352A/pt not_active Application Discontinuation
- 1997-06-16 EP EP97925215A patent/EP0912548A1/en not_active Withdrawn
- 1997-06-16 AU AU30441/97A patent/AU3044197A/en not_active Abandoned
- 1997-06-16 US US09/214,573 patent/US6417202B1/en not_active Expired - Fee Related
- 1997-06-18 HN HN1997000090A patent/HN1997000090A/es unknown
- 1997-06-19 PA PA19978432901A patent/PA8432901A1/es unknown
- 1997-07-08 MA MA24709A patent/MA26433A1/fr unknown
- 1997-07-08 AR ARP970103050A patent/AR007828A1/es unknown
- 1997-07-09 TN TNTNSN97119A patent/TNSN97119A1/fr unknown
- 1997-07-10 ID IDP972375A patent/ID19476A/id unknown
- 1997-07-11 HR HRPCT/IB96/00671A patent/HRP970378A2/hr not_active Application Discontinuation
- 1997-07-29 AP APAP/P/1997/001041A patent/AP9701041A0/en unknown

Also Published As

Publication number	Publication date
WO1998002430A1 (en)	1998-01-22
CA2260213C (en)	2005-03-29
TNSN97119A1 (fr)	2005-03-15
AP9701041A0 (en)	1999-01-10
AR007828A1 (es)	1999-11-24
ID19476A (id)	1998-07-16
AU3044197A (en)	1998-02-09
EP0912548A1 (en)	1999-05-06
CA2260213A1 (en)	1998-01-22
PA8432901A1 (es)	2000-05-24
BR9710352A (pt)	1999-08-17
MA26433A1 (fr)	2004-12-20
US6417202B1 (en)	2002-07-09
US20020049235A1 (en)	2002-04-25
HN1997000090A (es)	1997-12-26

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