IL118544A

IL118544A - History of imidazole, the process for their preparation and the pharmaceutical preparations containing them

History of imidazole, the process for their preparation and the pharmaceutical preparations containing them

Info

Publication number: IL118544A
Authority: IL; Israel
Prior art keywords: formula; alkyl; compound; optionally substituted; substituted
Prior art date: 1995-06-07

Application number

IL11854496A

Other languages

English (en)

Hebrew (he)

Other versions

IL118544A0 (en

Original Assignee

Smithkline Beecham Corp

Priority date

1995-06-07

Filing date

1996-06-03

Publication date

2001-08-08

1996-06-03 Application filed by Smithkline Beecham Corp filed Critical Smithkline Beecham Corp

1997-03-18 Publication of IL118544A0 publication Critical patent/IL118544A0/xx

2001-08-08 Publication of IL118544A publication Critical patent/IL118544A/en

Links

238000000034 method Methods 0.000 title claims description 92
230000008569 process Effects 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 17
239000008194 pharmaceutical composition Substances 0.000 title claims description 9
150000002460 imidazoles Chemical class 0.000 title abstract description 64
229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims description 235
125000000217 alkyl group Chemical group 0.000 claims description 180
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 175
-1 alkyl lithium Chemical compound 0.000 claims description 110
125000003118 aryl group Chemical group 0.000 claims description 69
125000000623 heterocyclic group Chemical group 0.000 claims description 61
125000001072 heteroaryl group Chemical group 0.000 claims description 55
201000010099 disease Diseases 0.000 claims description 46
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 46
239000001257 hydrogen Substances 0.000 claims description 43
229910052739 hydrogen Inorganic materials 0.000 claims description 43
238000006243 chemical reaction Methods 0.000 claims description 42
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims description 28
150000002466 imines Chemical class 0.000 claims description 25
125000001424 substituent group Chemical group 0.000 claims description 25
150000003839 salts Chemical class 0.000 claims description 24
238000004519 manufacturing process Methods 0.000 claims description 23
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 23
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
230000001404 mediated effect Effects 0.000 claims description 20
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
229910052760 oxygen Inorganic materials 0.000 claims description 19
229910052717 sulfur Inorganic materials 0.000 claims description 19
125000003107 substituted aryl group Chemical group 0.000 claims description 18
239000011593 sulfur Substances 0.000 claims description 18
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 17
230000015572 biosynthetic process Effects 0.000 claims description 17
229910052757 nitrogen Inorganic materials 0.000 claims description 17
239000001301 oxygen Substances 0.000 claims description 17
206010040070 Septic Shock Diseases 0.000 claims description 15
230000002757 inflammatory effect Effects 0.000 claims description 15
125000005842 heteroatom Chemical group 0.000 claims description 14
150000001299 aldehydes Chemical class 0.000 claims description 12
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 10
230000002685 pulmonary effect Effects 0.000 claims description 10
229910017711 NHRa Inorganic materials 0.000 claims description 9
125000005343 heterocyclic alkyl group Chemical group 0.000 claims description 9
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
239000002243 precursor Substances 0.000 claims description 8
201000005569 Gout Diseases 0.000 claims description 7
206010044248 Toxic shock syndrome Diseases 0.000 claims description 7
231100000650 Toxic shock syndrome Toxicity 0.000 claims description 7
229910052744 lithium Inorganic materials 0.000 claims description 7
102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 7
206010061218 Inflammation Diseases 0.000 claims description 6
239000003153 chemical reaction reagent Substances 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
230000004054 inflammatory process Effects 0.000 claims description 6
125000003386 piperidinyl group Chemical group 0.000 claims description 6
206010018634 Gouty Arthritis Diseases 0.000 claims description 5
230000002917 arthritic effect Effects 0.000 claims description 5
230000001684 chronic effect Effects 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
238000011065 in-situ storage Methods 0.000 claims description 5
208000006386 Bone Resorption Diseases 0.000 claims description 4
108091000080 Phosphotransferase Proteins 0.000 claims description 4
230000024279 bone resorption Effects 0.000 claims description 4
239000003937 drug carrier Substances 0.000 claims description 4
102000020233 phosphotransferase Human genes 0.000 claims description 4
206010038687 Respiratory distress Diseases 0.000 claims 2
208000025865 Ulcer Diseases 0.000 claims 2
230000002490 cerebral effect Effects 0.000 claims 2
231100000284 endotoxic Toxicity 0.000 claims 2
230000002346 endotoxic effect Effects 0.000 claims 2
230000010410 reperfusion Effects 0.000 claims 2
CCOXWRVWKFVFDG-UHFFFAOYSA-N pyrimidine-2-carbaldehyde Chemical compound O=CC1=NC=CC=N1 CCOXWRVWKFVFDG-UHFFFAOYSA-N 0.000 claims 1
102000004127 Cytokines Human genes 0.000 abstract description 49
108090000695 Cytokines Proteins 0.000 abstract description 49
239000000203 mixture Chemical class 0.000 abstract description 30
239000003112 inhibitor Substances 0.000 abstract description 7
238000002560 therapeutic procedure Methods 0.000 abstract description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 76
108060008682 Tumor Necrosis Factor Proteins 0.000 description 63
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 description 53
239000007787 solid Substances 0.000 description 51
238000011282 treatment Methods 0.000 description 40
210000004027 cell Anatomy 0.000 description 38
235000019439 ethyl acetate Nutrition 0.000 description 38
239000002904 solvent Substances 0.000 description 38
239000000243 solution Substances 0.000 description 35
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 34
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150000002367 halogens Chemical class 0.000 description 32
241000124008 Mammalia Species 0.000 description 31
229910052736 halogen Inorganic materials 0.000 description 31
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
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 30
229940096397 interleukin-8 Drugs 0.000 description 30
239000002585 base Substances 0.000 description 28
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
102000000589 Interleukin-1 Human genes 0.000 description 25
108010002352 Interleukin-1 Proteins 0.000 description 25
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 24
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 23
230000000875 corresponding effect Effects 0.000 description 23
230000002401 inhibitory effect Effects 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
230000014509 gene expression Effects 0.000 description 22
229910001868 water Inorganic materials 0.000 description 21
239000011541 reaction mixture Substances 0.000 description 20
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
125000000753 cycloalkyl group Chemical group 0.000 description 19
150000002431 hydrogen Chemical group 0.000 description 19
230000005764 inhibitory process Effects 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 17
241000700605 Viruses Species 0.000 description 17
238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 17
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
208000014674 injury Diseases 0.000 description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
208000027418 Wounds and injury Diseases 0.000 description 15
125000003710 aryl alkyl group Chemical group 0.000 description 15
230000006378 damage Effects 0.000 description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
239000003054 catalyst Substances 0.000 description 14
238000010438 heat treatment Methods 0.000 description 14
210000001616 monocyte Anatomy 0.000 description 14
GACUCTNCAUTQPH-UHFFFAOYSA-N 2-methylpyrimidine-4-carbothialdehyde Chemical compound CC1=NC=CC(C=S)=N1 GACUCTNCAUTQPH-UHFFFAOYSA-N 0.000 description 13
241000725303 Human immunodeficiency virus Species 0.000 description 13
108090001005 Interleukin-6 Proteins 0.000 description 13
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210000001744 T-lymphocyte Anatomy 0.000 description 13
125000003545 alkoxy group Chemical group 0.000 description 13
229940100601 interleukin-6 Drugs 0.000 description 13
150000002527 isonitriles Chemical class 0.000 description 13
108020004999 messenger RNA Proteins 0.000 description 13
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XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
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230000000694 effects Effects 0.000 description 12
125000001153 fluoro group Chemical group F* 0.000 description 12
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 12
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238000003786 synthesis reaction Methods 0.000 description 12
210000004556 brain Anatomy 0.000 description 11
239000012267 brine Substances 0.000 description 11
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238000003818 flash chromatography Methods 0.000 description 11
210000000440 neutrophil Anatomy 0.000 description 11
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
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125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 4
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