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
230000008020 evaporation Effects 0.000 description 8
238000001914 filtration Methods 0.000 description 8
125000004356 hydroxy functional group Chemical group O* 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
108010064593 Intercellular Adhesion Molecule-1 Proteins 0.000 description 7
102000015271 Intercellular Adhesion Molecule-1 Human genes 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 7
229910000041 hydrogen chloride Inorganic materials 0.000 description 7
210000000265 leukocyte Anatomy 0.000 description 7
239000002609 medium Substances 0.000 description 7
239000002244 precipitate Substances 0.000 description 7
239000012265 solid product Substances 0.000 description 7
108010024212 E-Selectin Proteins 0.000 description 6
102000004890 Interleukin-8 Human genes 0.000 description 6
108090001007 Interleukin-8 Proteins 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000002585 base Substances 0.000 description 6
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 6
230000002757 inflammatory effect Effects 0.000 description 6
XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 6
229940096397 interleukin-8 Drugs 0.000 description 6
210000000440 neutrophil Anatomy 0.000 description 6
QJPQVXSHYBGQGM-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 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 6
150000003233 pyrroles Chemical class 0.000 description 6
MGCGJBXTNWUHQE-UHFFFAOYSA-N quinoline-4-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CC=NC2=C1 MGCGJBXTNWUHQE-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
238000003786 synthesis reaction Methods 0.000 description 6
SURCGQGDUADKBL-UHFFFAOYSA-N 2-(2-hydroxyethylamino)-5-nitrobenzo[de]isoquinoline-1,3-dione Chemical compound [O-][N+](=O)C1=CC(C(N(NCCO)C2=O)=O)=C3C2=CC=CC3=C1 SURCGQGDUADKBL-UHFFFAOYSA-N 0.000 description 5
102100023471 E-selectin Human genes 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
238000002835 absorbance Methods 0.000 description 5
239000002253 acid Substances 0.000 description 5
238000005859 coupling reaction Methods 0.000 description 5
239000012043 crude product Substances 0.000 description 5
HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
239000003921 oil Substances 0.000 description 5
239000004533 oil dispersion Substances 0.000 description 5
235000019198 oils Nutrition 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
206010039073 rheumatoid arthritis Diseases 0.000 description 5
239000000126 substance Substances 0.000 description 5
238000012360 testing method Methods 0.000 description 5
210000001519 tissue Anatomy 0.000 description 5
239000008096 xylene Substances 0.000 description 5
PXCNNHUZRVQVBB-UHFFFAOYSA-N 1-(2-bromo-4-methyl-5-pyridin-4-yl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C1=C(Br)NC(C=2C=CN=CC=2)=C1C PXCNNHUZRVQVBB-UHFFFAOYSA-N 0.000 description 4
DVSOJRSUEOHWOS-UHFFFAOYSA-N 1-(4-methyl-2-phenyl-1h-pyrrol-3-yl)ethanone Chemical compound CC1=CNC(C=2C=CC=CC=2)=C1C(=O)C DVSOJRSUEOHWOS-UHFFFAOYSA-N 0.000 description 4
XTORSZAODKLOMN-UHFFFAOYSA-N 1-(4-methyl-5-pyridin-4-yl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C1=CNC(C=2C=CN=CC=2)=C1C XTORSZAODKLOMN-UHFFFAOYSA-N 0.000 description 4
206010001052 Acute respiratory distress syndrome Diseases 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
239000012980 RPMI-1640 medium Substances 0.000 description 4
208000013616 Respiratory Distress Syndrome Diseases 0.000 description 4
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
108010000134 Vascular Cell Adhesion Molecule-1 Proteins 0.000 description 4
102100023543 Vascular cell adhesion protein 1 Human genes 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 4
201000000028 adult respiratory distress syndrome Diseases 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
239000003814 drug Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
210000002889 endothelial cell Anatomy 0.000 description 4
239000002158 endotoxin Substances 0.000 description 4
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 4
239000002674 ointment Substances 0.000 description 4
125000002524 organometallic group Chemical group 0.000 description 4
239000002953 phosphate buffered saline Substances 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
239000002904 solvent Substances 0.000 description 4
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 4
239000011701 zinc Substances 0.000 description 4
WUUGDFUZGVWFSX-UHFFFAOYSA-N 1-(4-methyl-5-phenyl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C1=CNC(C=2C=CC=CC=2)=C1C WUUGDFUZGVWFSX-UHFFFAOYSA-N 0.000 description 3
ZQLNLLNDMBWRNR-UHFFFAOYSA-N 1-phenyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound O=C1CCCC=2C1=CNC=2C1=CC=CC=C1 ZQLNLLNDMBWRNR-UHFFFAOYSA-N 0.000 description 3
PYKJFEPAUKAXNN-UHFFFAOYSA-N 2-(2-methyl-8-phenylmethoxy-3-imidazo[1,2-a]pyridinyl)acetonitrile Chemical compound C=1C=CN2C(CC#N)=C(C)N=C2C=1OCC1=CC=CC=C1 PYKJFEPAUKAXNN-UHFFFAOYSA-N 0.000 description 3
FQPREIYYNITXAF-UHFFFAOYSA-N 2-bromo-3,5,5-trimethyl-6,7-dihydro-1h-indol-4-one Chemical compound C1CC(C)(C)C(=O)C2=C1NC(Br)=C2C FQPREIYYNITXAF-UHFFFAOYSA-N 0.000 description 3
MYAJIWDOWJNGEZ-UHFFFAOYSA-N 2-bromo-3,7,7-trimethyl-5,6-dihydro-1h-indol-4-one Chemical compound O=C1CCC(C)(C)C2=C1C(C)=C(Br)N2 MYAJIWDOWJNGEZ-UHFFFAOYSA-N 0.000 description 3
WTPIZLJDELCVED-UHFFFAOYSA-N 3,5,5-trimethyl-6,7-dihydro-1h-indol-4-one Chemical compound C1CC(C)(C)C(=O)C2=C1NC=C2C WTPIZLJDELCVED-UHFFFAOYSA-N 0.000 description 3
NBFQBQCXVOYXFH-UHFFFAOYSA-N 3,7,7-trimethyl-5,6-dihydro-1h-indol-4-one Chemical compound O=C1CCC(C)(C)C2=C1C(C)=CN2 NBFQBQCXVOYXFH-UHFFFAOYSA-N 0.000 description 3
PRRBQHNMYJRHFW-UHFFFAOYSA-M 3-oxoheptanoate Chemical compound CCCCC(=O)CC([O-])=O PRRBQHNMYJRHFW-UHFFFAOYSA-M 0.000 description 3
ZMNVMMGBWQNHKU-UHFFFAOYSA-N 3-phenyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12C(=O)CCCC2=CNC=1C1=CC=CC=C1 ZMNVMMGBWQNHKU-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
238000006069 Suzuki reaction reaction Methods 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
235000010338 boric acid Nutrition 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000005482 chemotactic factor Substances 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
229940079593 drug Drugs 0.000 description 3
230000003511 endothelial effect Effects 0.000 description 3
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
230000026030 halogenation Effects 0.000 description 3
238000005658 halogenation reaction Methods 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
230000003993 interaction Effects 0.000 description 3
239000010410 layer Substances 0.000 description 3
238000012417 linear regression Methods 0.000 description 3
229920006008 lipopolysaccharide Polymers 0.000 description 3
230000033001 locomotion Effects 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
201000008482 osteoarthritis Diseases 0.000 description 3
229910052763 palladium Inorganic materials 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
ALQUTEKNDPODSS-UHFFFAOYSA-N quinoline-4-carbaldehyde-oxime Natural products C1=CC=C2C(C=NO)=CC=NC2=C1 ALQUTEKNDPODSS-UHFFFAOYSA-N 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
230000000638 stimulation Effects 0.000 description 3
239000006228 supernatant Substances 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
UNEPXPMBVGDXGH-UHFFFAOYSA-N tributyl(pyridin-4-yl)stannane Chemical compound CCCC[Sn](CCCC)(CCCC)C1=CC=NC=C1 UNEPXPMBVGDXGH-UHFFFAOYSA-N 0.000 description 3
229910052725 zinc Inorganic materials 0.000 description 3
OVGLVOLWBBGQHS-RQOWECAXSA-N (1z)-1-hydroxyiminopropan-2-one Chemical compound CC(=O)\C=N/O OVGLVOLWBBGQHS-RQOWECAXSA-N 0.000 description 2
CYVVJSKZRBZHAV-UNZYHPAISA-N (2e,6e)-2,6-bis(pyridin-4-ylmethylidene)cyclohexan-1-one Chemical compound O=C1\C(=C\C=2C=CN=CC=2)CCC\C1=C/C1=CC=NC=C1 CYVVJSKZRBZHAV-UNZYHPAISA-N 0.000 description 2
LIZHCUCYKVWNDY-UHFFFAOYSA-N 1-(2,4-dimethyl-1h-pyrrol-3-yl)-2,2,2-trifluoroethanone Chemical compound CC1=CNC(C)=C1C(=O)C(F)(F)F LIZHCUCYKVWNDY-UHFFFAOYSA-N 0.000 description 2
CMTKNAXISUXFOY-UHFFFAOYSA-N 1-(2,4-dimethyl-5-pyridin-4-yl-1h-pyrrol-3-yl)-2,2,2-trifluoroethanone Chemical compound FC(F)(F)C(=O)C1=C(C)NC(C=2C=CN=CC=2)=C1C CMTKNAXISUXFOY-UHFFFAOYSA-N 0.000 description 2
JYWJSRYPAOHBID-UHFFFAOYSA-N 1-(5-bromo-2,4-dimethyl-1h-pyrrol-3-yl)-2,2,2-trifluoroethanone Chemical compound CC=1NC(Br)=C(C)C=1C(=O)C(F)(F)F JYWJSRYPAOHBID-UHFFFAOYSA-N 0.000 description 2
CLQIKPUIHJZKTM-UHFFFAOYSA-N 1-(5-bromo-4-methyl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C1=CNC(Br)=C1C CLQIKPUIHJZKTM-UHFFFAOYSA-N 0.000 description 2
FUVKGZAOMKCEHB-UHFFFAOYSA-N 1-(5-bromo-4-methyl-2-phenyl-1h-pyrrol-3-yl)ethanone Chemical compound CC1=C(Br)NC(C=2C=CC=CC=2)=C1C(=O)C FUVKGZAOMKCEHB-UHFFFAOYSA-N 0.000 description 2
JNDTXPLBMARXAO-UHFFFAOYSA-N 1-[2,4-dimethyl-1-(2-trimethylsilylethoxymethyl)pyrrol-3-yl]ethanone Chemical compound CC(=O)C=1C(C)=CN(COCC[Si](C)(C)C)C=1C JNDTXPLBMARXAO-UHFFFAOYSA-N 0.000 description 2
SBQQFVNPPMPWBW-UHFFFAOYSA-N 1-[4-(methoxymethyl)-2,5-dipyridin-4-yl-1h-pyrrol-3-yl]ethanone Chemical compound COCC=1C(C(C)=O)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 SBQQFVNPPMPWBW-UHFFFAOYSA-N 0.000 description 2
LINHWFUEUYKZSD-UHFFFAOYSA-N 1-[4-methyl-2-(4-methylsulfanylphenyl)-5-pyridin-4-yl-1h-pyrrol-3-yl]ethanone Chemical compound C1=CC(SC)=CC=C1C1=C(C(C)=O)C(C)=C(C=2C=CN=CC=2)N1 LINHWFUEUYKZSD-UHFFFAOYSA-N 0.000 description 2
JJOIDHFKZPDXCM-UHFFFAOYSA-N 1-phenyl-3-pyridin-4-yl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12C(=O)CCCC2=C(C=2C=CC=CC=2)NC=1C1=CC=NC=C1 JJOIDHFKZPDXCM-UHFFFAOYSA-N 0.000 description 2
LONQLMPIHRATJX-UHFFFAOYSA-N 2-bromo-3-methyl-1,5,6,7-tetrahydroindol-4-one Chemical compound C1CCC(=O)C2=C1NC(Br)=C2C LONQLMPIHRATJX-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
UKVMRYAHLAFWNO-UHFFFAOYSA-N 3,5,5-trimethyl-2-pyridin-4-yl-6,7-dihydro-1h-indol-4-one Chemical compound N1C=2CCC(C)(C)C(=O)C=2C(C)=C1C1=CC=NC=C1 UKVMRYAHLAFWNO-UHFFFAOYSA-N 0.000 description 2
WHSZIKFKIUHUEN-UHFFFAOYSA-N 3-bromo-1-phenyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12CCCC(=O)C2=C(Br)NC=1C1=CC=CC=C1 WHSZIKFKIUHUEN-UHFFFAOYSA-N 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
SNHVQHNXQVXZOU-UHFFFAOYSA-N 3-methyl-1,5,6,7-tetrahydroindol-4-one Chemical compound C1CCC(=O)C2=C1NC=C2C SNHVQHNXQVXZOU-UHFFFAOYSA-N 0.000 description 2
AFNBCZIMHKUDAB-UHFFFAOYSA-N 3-phenyl-1-pyridin-4-yl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C=12C(=O)CCCC2=C(C=2C=CN=CC=2)NC=1C1=CC=CC=C1 AFNBCZIMHKUDAB-UHFFFAOYSA-N 0.000 description 2
PXNRZJNTMDCHFR-UHFFFAOYSA-N 4-hydroxy-2-methyl-2,3-dihydropyran-6-one Chemical compound CC1CC(O)=CC(=O)O1 PXNRZJNTMDCHFR-UHFFFAOYSA-N 0.000 description 2
LKHUUFZEJCJBAX-UHFFFAOYSA-N 4-methyl-2,5-dipyridin-4-yl-1h-pyrrole-3-carbonitrile Chemical compound CC=1C(C#N)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 LKHUUFZEJCJBAX-UHFFFAOYSA-N 0.000 description 2
CBTWAEGIWMBHTC-UHFFFAOYSA-N 4-methyl-3-acetyl pyrrole Natural products CC(=O)C1=CNC=C1C CBTWAEGIWMBHTC-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
239000005695 Ammonium acetate Substances 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
XJUZRXYOEPSWMB-UHFFFAOYSA-N Chloromethyl methyl ether Chemical compound COCCl XJUZRXYOEPSWMB-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
238000002965 ELISA Methods 0.000 description 2
MGIXHQSSTZKVOO-UHFFFAOYSA-N Egomaketone Chemical compound CC(C)=CCC(=O)C=1C=COC=1 MGIXHQSSTZKVOO-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
206010018634 Gouty Arthritis Diseases 0.000 description 2
239000012981 Hank's balanced salt solution Substances 0.000 description 2
238000006736 Huisgen cycloaddition reaction Methods 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 2
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
201000001263 Psoriatic Arthritis Diseases 0.000 description 2
208000036824 Psoriatic arthropathy Diseases 0.000 description 2
206010063837 Reperfusion injury Diseases 0.000 description 2
229910006074 SO2NH2 Inorganic materials 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
206010044248 Toxic shock syndrome Diseases 0.000 description 2
231100000650 Toxic shock syndrome Toxicity 0.000 description 2
DBOLZNOZPSUKQT-UHFFFAOYSA-N [1-(methoxymethyl)-4-methyl-2,5-dipyridin-4-ylpyrrol-3-yl]methanol Chemical compound COCN1C(C=2C=CN=CC=2)=C(C)C(CO)=C1C1=CC=NC=C1 DBOLZNOZPSUKQT-UHFFFAOYSA-N 0.000 description 2
RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000003973 alkyl amines Chemical class 0.000 description 2
229940043376 ammonium acetate Drugs 0.000 description 2
235000019257 ammonium acetate Nutrition 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
FZIZEIAMIREUTN-UHFFFAOYSA-N azane;cerium(3+) Chemical compound N.[Ce+3] FZIZEIAMIREUTN-UHFFFAOYSA-N 0.000 description 2
230000009286 beneficial effect Effects 0.000 description 2
QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical group C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 2
YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
229910000085 borane Inorganic materials 0.000 description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
239000004327 boric acid Substances 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000000969 carrier Substances 0.000 description 2
230000001413 cellular effect Effects 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
229940061627 chloromethyl methyl ether Drugs 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000011097 chromatography purification Methods 0.000 description 2
230000001276 controlling effect Effects 0.000 description 2
230000008878 coupling Effects 0.000 description 2
238000010168 coupling process Methods 0.000 description 2
239000006071 cream Substances 0.000 description 2
FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 2
230000016396 cytokine production Effects 0.000 description 2
LRLPMKLRAJIMNA-UHFFFAOYSA-N diethyl(pyridin-4-yl)borane Chemical compound CCB(CC)C1=CC=NC=C1 LRLPMKLRAJIMNA-UHFFFAOYSA-N 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
210000003038 endothelium Anatomy 0.000 description 2
IXLFHEDTDLRCJC-UHFFFAOYSA-N ethyl 4-ethyl-2,5-dipyridin-4-yl-1h-pyrrole-3-carboxylate Chemical compound CCOC(=O)C=1C(CC)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 IXLFHEDTDLRCJC-UHFFFAOYSA-N 0.000 description 2
GHHVIAPGVFAGFW-UHFFFAOYSA-N ethyl 4-methyl-2,5-dipyridin-4-yl-1h-pyrrole-3-carboxylate Chemical compound CCOC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 GHHVIAPGVFAGFW-UHFFFAOYSA-N 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
239000001963 growth medium Substances 0.000 description 2
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 2
JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
230000006698 induction Effects 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
230000021995 interleukin-8 production Effects 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
239000007937 lozenge Substances 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
KKTREZWLSCWNRV-UHFFFAOYSA-N methyl 4-methyl-2-phenyl-1h-pyrrole-3-carboxylate Chemical compound CC1=CNC(C=2C=CC=CC=2)=C1C(=O)OC KKTREZWLSCWNRV-UHFFFAOYSA-N 0.000 description 2
WWTLEELMVPFCEN-UHFFFAOYSA-N methyl 4-methyl-2-phenyl-5-pyridin-4-yl-1h-pyrrole-3-carboxylate Chemical compound COC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=CC=C1 WWTLEELMVPFCEN-UHFFFAOYSA-N 0.000 description 2
KUCUHFKHCLFJPE-UHFFFAOYSA-N methyl 5-bromo-4-methyl-2-phenyl-1h-pyrrole-3-carboxylate Chemical compound CC1=C(Br)NC(C=2C=CC=CC=2)=C1C(=O)OC KUCUHFKHCLFJPE-UHFFFAOYSA-N 0.000 description 2
239000011259 mixed solution Substances 0.000 description 2
210000001616 monocyte Anatomy 0.000 description 2
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
239000006072 paste Substances 0.000 description 2
229940049954 penicillin Drugs 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
239000010452 phosphate Substances 0.000 description 2
229910000073 phosphorus hydride Inorganic materials 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
230000001105 regulatory effect Effects 0.000 description 2
239000011734 sodium Substances 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
229960005322 streptomycin Drugs 0.000 description 2
239000003826 tablet Substances 0.000 description 2
229940095064 tartrate Drugs 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
239000003981 vehicle Substances 0.000 description 2
VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 2
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 2
VNTJWIVWYDXXMF-UHFFFAOYSA-N (4-methyl-2,5-dipyridin-4-yl-1h-pyrrol-3-yl)methanol Chemical compound CC=1C(CO)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 VNTJWIVWYDXXMF-UHFFFAOYSA-N 0.000 description 1
DELJOESCKJGFML-DUXPYHPUSA-N (e)-3-aminobut-2-enenitrile Chemical compound C\C(N)=C/C#N DELJOESCKJGFML-DUXPYHPUSA-N 0.000 description 1
VLLHEPHWWIDUSS-ONEGZZNKSA-N (e)-4-methoxybut-3-en-2-one Chemical compound CO\C=C\C(C)=O VLLHEPHWWIDUSS-ONEGZZNKSA-N 0.000 description 1
SHXHPUAKLCCLDV-UHFFFAOYSA-N 1,1,1-trifluoropentane-2,4-dione Chemical compound CC(=O)CC(=O)C(F)(F)F SHXHPUAKLCCLDV-UHFFFAOYSA-N 0.000 description 1
GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
XQCIIVLJPAJQFK-UHFFFAOYSA-N 1-(2-ethenyl-4-methyl-5-pyridin-4-yl-1h-pyrrol-3-yl)ethanone Chemical compound N1C(C=C)=C(C(=O)C)C(C)=C1C1=CC=NC=C1 XQCIIVLJPAJQFK-UHFFFAOYSA-N 0.000 description 1
HABJDCFZOAQFLS-UHFFFAOYSA-N 1-(2-methyl-4,5-dipyridin-4-yl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C1=C(C)NC(C=2C=CN=CC=2)=C1C1=CC=NC=C1 HABJDCFZOAQFLS-UHFFFAOYSA-N 0.000 description 1
BIVFNKZXBRUIEA-UHFFFAOYSA-N 1-(2-methyl-5-pyridin-4-yl-1h-pyrrol-3-yl)ethanone Chemical compound N1C(C)=C(C(=O)C)C=C1C1=CC=NC=C1 BIVFNKZXBRUIEA-UHFFFAOYSA-N 0.000 description 1
AJDRJUSWCGIZBS-UHFFFAOYSA-N 1-(4-butyl-2,5-dipyridin-4-yl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C=1C(CCCC)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 AJDRJUSWCGIZBS-UHFFFAOYSA-N 0.000 description 1
SUZROVSSVDAROJ-UHFFFAOYSA-N 1-(4-methyl-2,5-dipyridin-4-yl-1h-pyrrol-3-yl)pentan-1-one Chemical compound CCCCC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 SUZROVSSVDAROJ-UHFFFAOYSA-N 0.000 description 1
LADHOSHDXKPKRA-UHFFFAOYSA-N 1-(4-methyl-2-naphthalen-1-yl-5-pyridin-4-yl-1h-pyrrol-3-yl)ethanone Chemical compound N1C(C=2C3=CC=CC=C3C=CC=2)=C(C(=O)C)C(C)=C1C1=CC=NC=C1 LADHOSHDXKPKRA-UHFFFAOYSA-N 0.000 description 1
HJBUEIFBCFTDHM-UHFFFAOYSA-N 1-(4-methyl-2-nitro-5-pyridin-4-yl-1h-pyrrol-3-yl)ethanone Chemical compound N1C([N+]([O-])=O)=C(C(=O)C)C(C)=C1C1=CC=NC=C1 HJBUEIFBCFTDHM-UHFFFAOYSA-N 0.000 description 1
VPYDZTAOCPPBLG-UHFFFAOYSA-N 1-(4-methyl-2-pyridin-3-yl-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=CN=C1 VPYDZTAOCPPBLG-UHFFFAOYSA-N 0.000 description 1
DQKAXZRUAGQUIW-UHFFFAOYSA-N 1-(4-methyl-2-pyridin-4-yl-5-quinolin-4-yl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C=1C(C)=C(C=2C3=CC=CC=C3N=CC=2)NC=1C1=CC=NC=C1 DQKAXZRUAGQUIW-UHFFFAOYSA-N 0.000 description 1
UFLZOVSTCOXPJW-UHFFFAOYSA-N 1-(4-methyl-5-phenyl-2-pyridin-4-yl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C=1C(C)=C(C=2C=CC=CC=2)NC=1C1=CC=NC=C1 UFLZOVSTCOXPJW-UHFFFAOYSA-N 0.000 description 1
GPZOVWNOWAKXPE-UHFFFAOYSA-N 1-(4-methyl-5-pyridin-4-yl-2-thiophen-2-yl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=CS1 GPZOVWNOWAKXPE-UHFFFAOYSA-N 0.000 description 1
YVAZCCZJUYUXQB-UHFFFAOYSA-N 1-(4-phenyl-2,5-dipyridin-4-yl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C1=C(C=2C=CN=CC=2)NC(C=2C=CN=CC=2)=C1C1=CC=CC=C1 YVAZCCZJUYUXQB-UHFFFAOYSA-N 0.000 description 1
JNBUBLZJTCLALT-UHFFFAOYSA-N 1-(4-propyl-2,5-dipyridin-4-yl-1h-pyrrol-3-yl)ethanone Chemical compound CC(=O)C=1C(CCC)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 JNBUBLZJTCLALT-UHFFFAOYSA-N 0.000 description 1
FYFKZIOCKPUXSL-UHFFFAOYSA-N 1-[1-(hydroxymethyl)-2,4-dimethyl-5-pyridin-4-ylpyrrol-3-yl]ethanone Chemical compound OCN1C(C)=C(C(=O)C)C(C)=C1C1=CC=NC=C1 FYFKZIOCKPUXSL-UHFFFAOYSA-N 0.000 description 1
BCYCWQYYTRYTAT-UHFFFAOYSA-N 1-[1-(methoxymethyl)-4-methyl-2,5-dipyridin-4-ylpyrrol-3-yl]ethanone Chemical compound COCN1C(C=2C=CN=CC=2)=C(C)C(C(C)=O)=C1C1=CC=NC=C1 BCYCWQYYTRYTAT-UHFFFAOYSA-N 0.000 description 1
ISSPCPFYGGMYLU-UHFFFAOYSA-N 1-[2-(3-aminophenyl)-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(N)=C1 ISSPCPFYGGMYLU-UHFFFAOYSA-N 0.000 description 1
UKSUMLCOZWDEEG-UHFFFAOYSA-N 1-[2-(hydroxymethyl)-4-methyl-5-pyridin-4-yl-1h-pyrrol-3-yl]ethanone Chemical compound N1C(CO)=C(C(=O)C)C(C)=C1C1=CC=NC=C1 UKSUMLCOZWDEEG-UHFFFAOYSA-N 0.000 description 1
CNLITEUSVJONGW-TXEJJXNPSA-N 1-[2-[(2r,6s)-2,6-dimethylmorpholin-4-yl]-4-methyl-5-pyridin-4-yl-1h-pyrrol-3-yl]ethanone Chemical compound C1[C@@H](C)O[C@@H](C)CN1C1=C(C(C)=O)C(C)=C(C=2C=CN=CC=2)N1 CNLITEUSVJONGW-TXEJJXNPSA-N 0.000 description 1
YNAPSRNZXWLTCM-UHFFFAOYSA-N 1-[2-[3-(4-fluorophenoxy)phenyl]-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=1C(C=1)=CC=CC=1OC1=CC=C(F)C=C1 YNAPSRNZXWLTCM-UHFFFAOYSA-N 0.000 description 1
WAOIVERRDWSMHV-UHFFFAOYSA-N 1-[4-(hydroxymethyl)-2,5-dipyridin-4-yl-1h-pyrrol-3-yl]ethanone Chemical compound CC(=O)C=1C(CO)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 WAOIVERRDWSMHV-UHFFFAOYSA-N 0.000 description 1
JBYHPELUKJLDIB-UHFFFAOYSA-N 1-[4-methyl-2,5-di(quinolin-4-yl)-1h-pyrrol-3-yl]ethanone Chemical compound C1=CC=C2C(C3=C(C)C(=C(N3)C=3C4=CC=CC=C4N=CC=3)C(=O)C)=CC=NC2=C1 JBYHPELUKJLDIB-UHFFFAOYSA-N 0.000 description 1
XWKLWMVBKZPYOZ-UHFFFAOYSA-N 1-[4-methyl-2-(3-nitrophenyl)-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([N+]([O-])=O)=C1 XWKLWMVBKZPYOZ-UHFFFAOYSA-N 0.000 description 1
MBKVCZOSEIJGPG-UHFFFAOYSA-N 1-[4-methyl-2-(4-methylsulfinylphenyl)-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(S(C)=O)C=C1 MBKVCZOSEIJGPG-UHFFFAOYSA-N 0.000 description 1
BBMLMGQAIAYGJZ-UHFFFAOYSA-N 1-[4-methyl-5-pyridin-4-yl-2-(4-pyridin-2-ylpiperazin-1-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=N1 BBMLMGQAIAYGJZ-UHFFFAOYSA-N 0.000 description 1
PBBCRTMNFNUDSZ-UHFFFAOYSA-N 1-[4-methyl-5-pyridin-4-yl-2-[4-(trifluoromethyl)phenyl]-1h-pyrrol-3-yl]ethanone Chemical compound CC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=C(C(F)(F)F)C=C1 PBBCRTMNFNUDSZ-UHFFFAOYSA-N 0.000 description 1
LOBHNFJMQKDEOO-UHFFFAOYSA-N 1-[5-bromo-2,4-dimethyl-1-(2-trimethylsilylethoxymethyl)pyrrol-3-yl]ethanone Chemical compound CC(=O)C=1C(C)=C(Br)N(COCC[Si](C)(C)C)C=1C LOBHNFJMQKDEOO-UHFFFAOYSA-N 0.000 description 1
PLWANCOYVAFWCA-UHFFFAOYSA-N 1-amino-1-phenylpropan-2-one;hydrochloride Chemical compound Cl.CC(=O)C(N)C1=CC=CC=C1 PLWANCOYVAFWCA-UHFFFAOYSA-N 0.000 description 1
HXNCEYUSHNQTKV-UHFFFAOYSA-N 1-bromo-3-phenyl-2,5,6,7-tetrahydroisoindol-4-one Chemical compound C1CCC(=O)C=2C1=C(Br)NC=2C1=CC=CC=C1 HXNCEYUSHNQTKV-UHFFFAOYSA-N 0.000 description 1
125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
XTIGGAHUZJWQMD-UHFFFAOYSA-N 1-chloro-2-methoxyethane Chemical compound COCCCl XTIGGAHUZJWQMD-UHFFFAOYSA-N 0.000 description 1
DUZVTUSLKJEJIA-UHFFFAOYSA-M 1-heptylpyridin-1-ium;bromide Chemical compound [Br-].CCCCCCC[N+]1=CC=CC=C1 DUZVTUSLKJEJIA-UHFFFAOYSA-M 0.000 description 1
FVSYUWGGSGJDEB-UHFFFAOYSA-N 1-hydroxyimino-1-pyridin-4-ylpropan-2-one Chemical compound CC(=O)C(=NO)C1=CC=NC=C1 FVSYUWGGSGJDEB-UHFFFAOYSA-N 0.000 description 1
125000006017 1-propenyl group Chemical group 0.000 description 1
AOPBDTHQAIWWMI-UHFFFAOYSA-N 2,2-dimethylcyclohexane-1,3-dione Chemical compound CC1(C)C(=O)CCCC1=O AOPBDTHQAIWWMI-UHFFFAOYSA-N 0.000 description 1
NGGDTWNURWLVMC-UHFFFAOYSA-N 2-(1h-pyrrol-2-yl)pyridine Chemical class C1=CNC(C=2N=CC=CC=2)=C1 NGGDTWNURWLVMC-UHFFFAOYSA-N 0.000 description 1
VIRSFQIJOFMOPY-UHFFFAOYSA-N 2-(5-quinolin-2-yl-1h-pyrrol-2-yl)quinoline Chemical compound C1=CC=CC2=NC(C3=CC=C(N3)C=3N=C4C=CC=CC4=CC=3)=CC=C21 VIRSFQIJOFMOPY-UHFFFAOYSA-N 0.000 description 1
BPXKZEMBEZGUAH-UHFFFAOYSA-N 2-(chloromethoxy)ethyl-trimethylsilane Chemical compound C[Si](C)(C)CCOCCl BPXKZEMBEZGUAH-UHFFFAOYSA-N 0.000 description 1
RGALBQILADNMKA-UHFFFAOYSA-N 2-bromo-1-pyridin-4-ylethanone;hydron;bromide Chemical compound Br.BrCC(=O)C1=CC=NC=C1 RGALBQILADNMKA-UHFFFAOYSA-N 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
ZUOOIRRDMPIIJM-UHFFFAOYSA-N 2-methoxyethyl 4-methyl-2,5-dipyridin-4-yl-1h-pyrrole-3-carboxylate Chemical compound COCCOC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 ZUOOIRRDMPIIJM-UHFFFAOYSA-N 0.000 description 1
125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
BMLKSMGUVMXKQS-UHFFFAOYSA-N 2-phenylcyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1C1=CC=CC=C1 BMLKSMGUVMXKQS-UHFFFAOYSA-N 0.000 description 1
NPUKDXXFDDZOKR-UHFFFAOYSA-N 3-(1-phenylethyl)-4-imidazolecarboxylic acid ethyl ester Chemical compound CCOC(=O)C1=CN=CN1C(C)C1=CC=CC=C1 NPUKDXXFDDZOKR-UHFFFAOYSA-N 0.000 description 1
FUPTWJOBSSOLJO-UHFFFAOYSA-N 3-acetyl-4-methyl-5-pyridin-4-yl-1h-pyrrole-2-carbaldehyde Chemical compound N1C(C=O)=C(C(=O)C)C(C)=C1C1=CC=NC=C1 FUPTWJOBSSOLJO-UHFFFAOYSA-N 0.000 description 1
FWXAUDSWDBGCMN-UHFFFAOYSA-N 3-diphenylphosphanylbutan-2-yl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)C(C)C(C)P(C=1C=CC=CC=1)C1=CC=CC=C1 FWXAUDSWDBGCMN-UHFFFAOYSA-N 0.000 description 1
LGXOVPGEBDUENZ-UHFFFAOYSA-N 3-methyl-1-(4-methyl-2,5-dipyridin-4-yl-1h-pyrrol-3-yl)butan-1-one Chemical compound CC(C)CC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 LGXOVPGEBDUENZ-UHFFFAOYSA-N 0.000 description 1
SDKCIWOUARPPPX-UHFFFAOYSA-N 3-methyl-2-pyridin-4-yl-1,7-dihydrothiopyrano[3,4-b]pyrrol-4-one Chemical compound N1C=2CSCC(=O)C=2C(C)=C1C1=CC=NC=C1 SDKCIWOUARPPPX-UHFFFAOYSA-N 0.000 description 1
CKHRDHIRPFEDAD-UHFFFAOYSA-N 3-methyl-6-phenyl-2-pyridin-4-yl-1,5,6,7-tetrahydroindol-4-one Chemical compound C1C(=O)C=2C(C)=C(C=3C=CN=CC=3)NC=2CC1C1=CC=CC=C1 CKHRDHIRPFEDAD-UHFFFAOYSA-N 0.000 description 1
PJCCSZUMZMCWSX-UHFFFAOYSA-N 4,4-Dimethoxy-2-butanone Chemical compound COC(OC)CC(C)=O PJCCSZUMZMCWSX-UHFFFAOYSA-N 0.000 description 1
PLGPBTCNKJQJHQ-UHFFFAOYSA-N 4,4-dimethylcyclohexane-1,3-dione Chemical compound CC1(C)CCC(=O)CC1=O PLGPBTCNKJQJHQ-UHFFFAOYSA-N 0.000 description 1
JHJSHAORWYRPPF-UHFFFAOYSA-N 4-(3-methyl-4-methylsulfonyl-5-pyridin-4-yl-1h-pyrrol-2-yl)pyridine Chemical compound CS(=O)(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 JHJSHAORWYRPPF-UHFFFAOYSA-N 0.000 description 1
LBUNNMJLXWQQBY-UHFFFAOYSA-N 4-fluorophenylboronic acid Chemical compound OB(O)C1=CC=C(F)C=C1 LBUNNMJLXWQQBY-UHFFFAOYSA-N 0.000 description 1
IKALLWCKWBIZOW-UHFFFAOYSA-N 4-methyl-2,5-dipyridin-4-yl-1h-pyrrole-3-carbaldehyde Chemical compound CC=1C(C=O)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 IKALLWCKWBIZOW-UHFFFAOYSA-N 0.000 description 1
PGSOORCBXGRVKQ-UHFFFAOYSA-N 4-methyl-2,5-dipyridin-4-yl-1h-pyrrole-3-carboxamide Chemical compound NC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 PGSOORCBXGRVKQ-UHFFFAOYSA-N 0.000 description 1
XHTRHEMAXFRQDD-UHFFFAOYSA-N 4-methyl-N-(4-methylbenzoyl)iminobenzamide Chemical compound C1=CC(C)=CC=C1C(=O)N=NC(=O)C1=CC=C(C)C=C1 XHTRHEMAXFRQDD-UHFFFAOYSA-N 0.000 description 1
AHIFRRRKIUGPLQ-UHFFFAOYSA-N 5-(3-pyridin-2-yl-1h-pyrrol-2-yl)quinoline Chemical class C=1C=CC2=NC=CC=C2C=1C=1NC=CC=1C1=CC=CC=N1 AHIFRRRKIUGPLQ-UHFFFAOYSA-N 0.000 description 1
DMIIMPQQPXUKOO-UHFFFAOYSA-N 5-methylcyclohexane-1,3-dione Chemical compound CC1CC(=O)CC(=O)C1 DMIIMPQQPXUKOO-UHFFFAOYSA-N 0.000 description 1
IGMOYJSFRIASIE-UHFFFAOYSA-N 6-Methylheptan-2,4-dione Chemical compound CC(C)CC(=O)CC(C)=O IGMOYJSFRIASIE-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
206010002556 Ankylosing Spondylitis Diseases 0.000 description 1
108020000948 Antisense Oligonucleotides Proteins 0.000 description 1
201000001320 Atherosclerosis Diseases 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
AQNKDHDMTRVWFF-UHFFFAOYSA-N CC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=[N+]([O-])C=C1 Chemical class CC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=[N+]([O-])C=C1 AQNKDHDMTRVWFF-UHFFFAOYSA-N 0.000 description 1
CSHPPDBKEPSYMG-UHFFFAOYSA-N CC(=O)C=1C(C)=C(C=2C=C[N+]([O-])=CC=2)NC=1C1=CC=NC=C1 Chemical compound CC(=O)C=1C(C)=C(C=2C=C[N+]([O-])=CC=2)NC=1C1=CC=NC=C1 CSHPPDBKEPSYMG-UHFFFAOYSA-N 0.000 description 1
101100289995 Caenorhabditis elegans mac-1 gene Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
206010063094 Cerebral malaria Diseases 0.000 description 1
208000017667 Chronic Disease Diseases 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
206010009900 Colitis ulcerative Diseases 0.000 description 1
DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-N 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
108010092160 Dactinomycin Proteins 0.000 description 1
208000037487 Endotoxemia Diseases 0.000 description 1
102000004190 Enzymes Human genes 0.000 description 1
108090000790 Enzymes Proteins 0.000 description 1
PAEYAKGINDQUCT-UHFFFAOYSA-N Ethyl 2-pyrrolecarboxylate Chemical class CCOC(=O)C1=CC=CN1 PAEYAKGINDQUCT-UHFFFAOYSA-N 0.000 description 1
208000001640 Fibromyalgia Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
241000282412 Homo Species 0.000 description 1
101001046686 Homo sapiens Integrin alpha-M Proteins 0.000 description 1
101000935040 Homo sapiens Integrin beta-2 Proteins 0.000 description 1
101000611183 Homo sapiens Tumor necrosis factor Proteins 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
238000012404 In vitro experiment Methods 0.000 description 1
102100022338 Integrin alpha-M Human genes 0.000 description 1
102100025390 Integrin beta-2 Human genes 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
208000019693 Lung disease Diseases 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
240000003183 Manihot esculenta Species 0.000 description 1
235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
102000018697 Membrane Proteins Human genes 0.000 description 1
108010052285 Membrane Proteins Proteins 0.000 description 1
206010027476 Metastases Diseases 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
244000179886 Moringa oleifera Species 0.000 description 1
235000011347 Moringa oleifera Nutrition 0.000 description 1
239000007832 Na2SO4 Substances 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
235000019483 Peanut oil Nutrition 0.000 description 1
241001494479 Pecora Species 0.000 description 1
102000003992 Peroxidases Human genes 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
206010037660 Pyrexia Diseases 0.000 description 1
208000033464 Reiter syndrome Diseases 0.000 description 1
241000219061 Rheum Species 0.000 description 1
IFCPVHSQXSHLRI-UHFFFAOYSA-N S-amino pyridine-4-carbothioate Chemical class NSC(=O)C1=CC=NC=C1 IFCPVHSQXSHLRI-UHFFFAOYSA-N 0.000 description 1
244000000231 Sesamum indicum Species 0.000 description 1
201000010001 Silicosis Diseases 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
238000006619 Stille reaction Methods 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
210000001744 T-lymphocyte Anatomy 0.000 description 1
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
206010048873 Traumatic arthritis Diseases 0.000 description 1
GCTFWCDSFPMHHS-UHFFFAOYSA-M Tributyltin chloride Chemical compound CCCC[Sn](Cl)(CCCC)CCCC GCTFWCDSFPMHHS-UHFFFAOYSA-M 0.000 description 1
235000021307 Triticum Nutrition 0.000 description 1
244000098338 Triticum aestivum Species 0.000 description 1
102000004142 Trypsin Human genes 0.000 description 1
108090000631 Trypsin Proteins 0.000 description 1
108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 description 1
102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 1
206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
201000006704 Ulcerative Colitis Diseases 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
UXWZJQHQCUDAMN-UHFFFAOYSA-N [NH2+]1CCOCC1.C(=O)([O-])C1=C(NC(=C1C)C1=CC=NC=C1)C1=CC=NC=C1 Chemical compound [NH2+]1CCOCC1.C(=O)([O-])C1=C(NC(=C1C)C1=CC=NC=C1)C1=CC=NC=C1 UXWZJQHQCUDAMN-UHFFFAOYSA-N 0.000 description 1
238000000862 absorption spectrum Methods 0.000 description 1
RJURFGZVJUQBHK-IIXSONLDSA-N actinomycin D Chemical compound C[C@H]1OC(=O)[C@H](C(C)C)N(C)C(=O)CN(C)C(=O)[C@@H]2CCCN2C(=O)[C@@H](C(C)C)NC(=O)[C@H]1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)N[C@@H]4C(=O)N[C@@H](C(N5CCC[C@H]5C(=O)N(C)CC(=O)N(C)[C@@H](C(C)C)C(=O)O[C@@H]4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-IIXSONLDSA-N 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000001464 adherent effect Effects 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
125000003342 alkenyl group Chemical group 0.000 description 1
125000005157 alkyl carboxy group Chemical group 0.000 description 1
150000001351 alkyl iodides Chemical class 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
230000001668 ameliorated effect Effects 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
230000033115 angiogenesis Effects 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
239000005557 antagonist Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
230000000843 anti-fungal effect Effects 0.000 description 1
230000000890 antigenic effect Effects 0.000 description 1
239000000074 antisense oligonucleotide Substances 0.000 description 1
238000012230 antisense oligonucleotides Methods 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
230000002917 arthritic effect Effects 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
210000003651 basophil Anatomy 0.000 description 1
229940077388 benzenesulfonate Drugs 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
PFZJOQANUUEHGP-UHFFFAOYSA-N benzyl 4-methyl-2,5-dipyridin-4-yl-1h-pyrrole-3-carboxylate Chemical compound C=1C=NC=CC=1C=1NC(C=2C=CN=CC=2)=C(C)C=1C(=O)OCC1=CC=CC=C1 PFZJOQANUUEHGP-UHFFFAOYSA-N 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000033228 biological regulation Effects 0.000 description 1
230000008512 biological response Effects 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
239000008280 blood Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
208000019664 bone resorption disease Diseases 0.000 description 1
125000005619 boric acid group Chemical class 0.000 description 1
125000005620 boronic acid group Chemical class 0.000 description 1
125000005382 boronyl group Chemical group 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
244000309464 bull Species 0.000 description 1
239000001273 butane Substances 0.000 description 1
RORCGVYADSDJEZ-UHFFFAOYSA-N butyl 4-methyl-2,5-dipyridin-4-yl-1h-pyrrole-3-carboxylate Chemical compound CCCCOC(=O)C=1C(C)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 RORCGVYADSDJEZ-UHFFFAOYSA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000002775 capsule Substances 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000021164 cell adhesion Effects 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
230000009087 cell motility Effects 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000002975 chemoattractant Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
KWTSZCJMWHGPOS-UHFFFAOYSA-M chloro(trimethyl)stannane Chemical compound C[Sn](C)(C)Cl KWTSZCJMWHGPOS-UHFFFAOYSA-M 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000006352 cycloaddition reaction Methods 0.000 description 1
DBOVMTXPZWVYAQ-UHFFFAOYSA-N cycloheptane-1,3-dione Chemical compound O=C1CCCCC(=O)C1 DBOVMTXPZWVYAQ-UHFFFAOYSA-N 0.000 description 1
238000002784 cytotoxicity assay Methods 0.000 description 1
231100000263 cytotoxicity test Toxicity 0.000 description 1
229960000640 dactinomycin Drugs 0.000 description 1
230000007850 degeneration Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
206010012601 diabetes mellitus Diseases 0.000 description 1
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
FESAXEDIWWXCNG-UHFFFAOYSA-N diethyl(methoxy)borane Chemical compound CCB(CC)OC FESAXEDIWWXCNG-UHFFFAOYSA-N 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
235000019797 dipotassium phosphate Nutrition 0.000 description 1
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000000975 dye Substances 0.000 description 1
125000006575 electron-withdrawing group Chemical group 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
150000002084 enol ethers Chemical class 0.000 description 1
210000002919 epithelial cell Anatomy 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
GCFHZZWXZLABBL-UHFFFAOYSA-N ethanol;hexane Chemical compound CCO.CCCCCC GCFHZZWXZLABBL-UHFFFAOYSA-N 0.000 description 1
JRDCIMZBDJFAII-UHFFFAOYSA-N ethyl 1-(methoxymethyl)-4-methyl-2,5-dipyridin-4-ylpyrrole-3-carboxylate Chemical compound COCN1C(C=2C=CN=CC=2)=C(C(=O)OCC)C(C)=C1C1=CC=NC=C1 JRDCIMZBDJFAII-UHFFFAOYSA-N 0.000 description 1
VGBSBLHKCHAVHU-UHFFFAOYSA-N ethyl 2,4-dimethyl-5-pyridin-4-yl-1h-pyrrole-3-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(C=2C=CN=CC=2)=C1C VGBSBLHKCHAVHU-UHFFFAOYSA-N 0.000 description 1
PCJNYGPKMQQCPX-UHFFFAOYSA-N ethyl 3-oxo-3-pyridin-4-ylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=NC=C1 PCJNYGPKMQQCPX-UHFFFAOYSA-N 0.000 description 1
LLQWWTFKILFIRI-UHFFFAOYSA-N ethyl 4-(4-nitrophenyl)-2,5-dipyridin-4-yl-1h-pyrrole-3-carboxylate Chemical compound CCOC(=O)C1=C(C=2C=CN=CC=2)NC(C=2C=CN=CC=2)=C1C1=CC=C([N+]([O-])=O)C=C1 LLQWWTFKILFIRI-UHFFFAOYSA-N 0.000 description 1
MGKYEWWFHSESJN-UHFFFAOYSA-N ethyl 4-[methyl-(2-phenyl-1,3-thiazol-4-yl)amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N(C)C1=CSC(C=2C=CC=CC=2)=N1 MGKYEWWFHSESJN-UHFFFAOYSA-N 0.000 description 1
XTTKBKPVIUXLHF-UHFFFAOYSA-N ethyl 4-butyl-2,5-dipyridin-4-yl-1h-pyrrole-3-carboxylate Chemical compound CCCCC=1C(C(=O)OCC)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 XTTKBKPVIUXLHF-UHFFFAOYSA-N 0.000 description 1
SYTMRBYQZWJKNL-UHFFFAOYSA-N ethyl 4-phenyl-2,5-dipyridin-4-yl-1h-pyrrole-3-carboxylate Chemical compound CCOC(=O)C1=C(C=2C=CN=CC=2)NC(C=2C=CN=CC=2)=C1C1=CC=CC=C1 SYTMRBYQZWJKNL-UHFFFAOYSA-N 0.000 description 1
FPVNNYXQNDYEDT-UHFFFAOYSA-N ethyl 4-propan-2-yl-2,5-dipyridin-4-yl-1h-pyrrole-3-carboxylate Chemical compound CC(C)C=1C(C(=O)OCC)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 FPVNNYXQNDYEDT-UHFFFAOYSA-N 0.000 description 1
VMUDJEAKISMZFT-UHFFFAOYSA-N ethyl 4-propyl-2,5-dipyridin-4-yl-1h-pyrrole-3-carboxylate Chemical compound CCCC=1C(C(=O)OCC)=C(C=2C=CN=CC=2)NC=1C1=CC=NC=C1 VMUDJEAKISMZFT-UHFFFAOYSA-N 0.000 description 1
ZZENCVNULWKCNC-UHFFFAOYSA-N ethyl 5-bromo-2,4-dimethyl-1h-pyrrole-3-carboxylate Chemical compound CCOC(=O)C1=C(C)NC(Br)=C1C ZZENCVNULWKCNC-UHFFFAOYSA-N 0.000 description 1
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
230000005284 excitation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012894 fetal calf serum Substances 0.000 description 1
210000002950 fibroblast Anatomy 0.000 description 1
239000012997 ficoll-paque Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
239000012530 fluid Substances 0.000 description 1
239000007850 fluorescent dye Substances 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000012634 fragment Substances 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
230000006870 function Effects 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
229940050410 gluconate Drugs 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
230000003179 granulation Effects 0.000 description 1
238000005469 granulation Methods 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
208000006454 hepatitis Diseases 0.000 description 1
231100000283 hepatitis Toxicity 0.000 description 1
125000001072 heteroaryl group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
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
230000008595 infiltration Effects 0.000 description 1
238000001764 infiltration Methods 0.000 description 1
230000004968 inflammatory condition Effects 0.000 description 1
230000028709 inflammatory response Effects 0.000 description 1
206010022000 influenza Diseases 0.000 description 1
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
208000028867 ischemia Diseases 0.000 description 1
125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
235000015110 jellies Nutrition 0.000 description 1
208000011379 keloid formation Diseases 0.000 description 1
210000002510 keratinocyte Anatomy 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000003446 ligand Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000006210 lotion Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
230000002132 lysosomal effect Effects 0.000 description 1
210000002540 macrophage Anatomy 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
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
230000007246 mechanism Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
230000009401 metastasis Effects 0.000 description 1
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 (fr)
EP (1)	EP0912548A1 (fr)
AP (1)	AP9701041A0 (fr)
AR (1)	AR007828A1 (fr)
AU (1)	AU3044197A (fr)
BR (1)	BR9710352A (fr)
CA (1)	CA2260213C (fr)
HN (1)	HN1997000090A (fr)
HR (1)	HRP970378A2 (fr)
ID (1)	ID19476A (fr)
MA (1)	MA26433A1 (fr)
PA (1)	PA8432901A1 (fr)
TN (1)	TNSN97119A1 (fr)
WO (1)	WO1998002430A1 (fr)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6147080A (en) *	1996-12-18	2000-11-14	Vertex Pharmaceuticals Incorporated	Inhibitors of p38
US5945418A (en) *	1996-12-18	1999-08-31	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
ATE295166T1 (de) *	1998-01-14	2005-05-15	Nippon Shinyaku Co Ltd	Aktivatoren der kalium-kanäle
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
WO2000069847A1 (fr) *	1999-05-14	2000-11-23	Ortho-Mcneil Pharmaceutical, Inc.	3-pyridyle-4-arylpyrroles substitues et methodes prophylactiques et therapeutiques associees
AU7961100A (en) *	1999-10-28	2001-05-08	Daiichi Pharmaceutical Co., Ltd.	Drug discharge pump inhibitors
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
CA2435141A1 (fr) *	2001-01-18	2002-07-25	Sankyo Company, Limited	Compositions destinees a la prevention et au traitement de l'hepatopathie
JPWO2002087589A1 (ja) *	2001-04-26	2004-08-12	第一製薬株式会社	薬剤排出ポンプ阻害薬
US7056917B2 (en) *	2001-04-26	2006-06-06	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
JP2005506324A (ja)	2001-08-30	2005-03-03	エフ．ホフマン−ラ　ロシュ　アーゲー	抗炎症剤としてのアミノピロール化合物
CN1747949A (zh) *	2002-12-20	2006-03-15	法马西亚公司	无环吡唑化合物
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
US20070185106A1 (en) *	2004-02-20	2007-08-09	Astrazeneca Ab	Pyrrole derivatives as gonadotropin releasing hormone (gnrh) antagonists
US7618982B2 (en) *	2005-12-19	2009-11-17	Nerviano Medical Sciences S.R.L.	Heteroarylpyrrolopyridinones active as kinase inhibitors
CA2632565A1 (fr) *	2005-12-19	2007-07-05	Syngenta Limited	Composes heterocycliques aromatiques substitues en tant que fongicides
ZA200808966B (en) *	2006-03-27	2010-03-31	Nerviano Medical Sciences Srl	Pyridyl- and pyrimidinyl-substituted pyrrole-, thiophene- and furane-derivatives as kinase inhibitors
BRPI0717097A2 (pt)	2006-09-21	2013-11-26	Novartis Ag	Derivados de pirrol úteis para o tratamento de doenças mediadas por citocina
EP2838881B1 (fr) *	2012-04-20	2018-08-08	AbbVie Inc.	Dérivés d'iso-indolone
CN104379573A (zh) *	2012-04-20	2015-02-25	艾伯维公司	异吲哚酮衍生物
EP2970193B1 (fr) *	2013-03-12	2018-07-25	AbbVie Inc.	Inhibiteurs de pyrrole-amide
AR100886A1 (es)	2014-06-17	2016-11-09	Bayer Pharma AG	3-amino-1,5,6,7-tetrahidro-4h-indol-4-onas
EP3390401A1 (fr) *	2015-12-16	2018-10-24	Bayer Pharma Aktiengesellschaft	Hétéro-1,5,6,7-tétrahydro-4h-indol-4-ones

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5356897A (en)	1991-09-09	1994-10-18	Fujisawa Pharmaceutical Co., Ltd.	3-(heteroaryl)-pyrazololi[1,5-a]pyrimidines
WO1997005878A1 (fr) *	1995-08-10	1997-02-20	Merck & Co., Inc.	Pyrroles d'aryle substitues en position 2 et 5, compositions contenant de tels composes et leurs modes d'utilisation
WO1997005877A1 (fr) *	1995-08-10	1997-02-20	Merck & Co., Inc.	Pyrroles d'aryle substitues en position 2, compositions contenant de tels composes et leurs modes d'utilisation
EP0859771A4 (fr)	1995-10-31	2000-03-15	Merck & Co Inc	Pyrroles de pyridyle substitues, compositions contenant de tels composes et mode d'utilisation
AU7529096A (en)	1995-10-31	1997-05-22	Merck & Co., Inc.	Substituted aryl pyrroles, compositions containing such compounds and methods of use
WO1997016441A1 (fr)	1995-10-31	1997-05-09	Merck & Co., Inc.	Pyrroles aryliques de substitution, compositions renfermant de telles composes et methodes d'utilisation de ces substances
US5776954A (en) *	1996-10-30	1998-07-07	Merck & Co., Inc.	Substituted pyridyl pyrroles, compositions containing such compounds and methods of use

1997
- 1997-06-16 BR BR9710352A patent/BR9710352A/pt not_active Application Discontinuation
- 1997-06-16 EP EP97925215A patent/EP0912548A1/fr not_active Withdrawn
- 1997-06-16 CA CA002260213A patent/CA2260213C/fr not_active Expired - Fee Related
- 1997-06-16 AU AU30441/97A patent/AU3044197A/en not_active Abandoned
- 1997-06-16 WO PCT/IB1997/000703 patent/WO1998002430A1/fr not_active Ceased
- 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
EP0912548A1 (fr)	1999-05-06
TNSN97119A1 (fr)	2005-03-15
HN1997000090A (es)	1997-12-26
CA2260213C (fr)	2005-03-29
US6417202B1 (en)	2002-07-09
PA8432901A1 (es)	2000-05-24
ID19476A (id)	1998-07-16
US20020049235A1 (en)	2002-04-25
AR007828A1 (es)	1999-11-24
MA26433A1 (fr)	2004-12-20
AP9701041A0 (en)	1999-01-10
WO1998002430A1 (fr)	1998-01-22
AU3044197A (en)	1998-02-09
BR9710352A (pt)	1999-08-17
CA2260213A1 (fr)	1998-01-22

Legal Events

Date

Code

Title

Description

1998-07-11

ODRP

Renewal fee for the maintenance of a patent

Payment date: 19980711

Year of fee payment: 2