HRP970378A2

HRP970378A2 - Pyridylpyrrole compounds

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

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
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