DE69626513T2 - Imidazolverbindungen - Google Patents
ImidazolverbindungenInfo
- Publication number
- DE69626513T2 DE69626513T2 DE69626513T DE69626513T DE69626513T2 DE 69626513 T2 DE69626513 T2 DE 69626513T2 DE 69626513 T DE69626513 T DE 69626513T DE 69626513 T DE69626513 T DE 69626513T DE 69626513 T2 DE69626513 T2 DE 69626513T2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- formula
- substituted
- imidazole
- aryl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims description 206
- 150000002460 imidazoles Chemical class 0.000 claims abstract description 89
- 150000001875 compounds Chemical class 0.000 claims description 221
- -1 1-imidazolyl Chemical group 0.000 claims description 108
- 238000000034 method Methods 0.000 claims description 77
- 125000003118 aryl group Chemical group 0.000 claims description 61
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 59
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 54
- 125000000623 heterocyclic group Chemical group 0.000 claims description 51
- 238000006243 chemical reaction Methods 0.000 claims description 45
- 125000001072 heteroaryl group Chemical group 0.000 claims description 45
- 201000010099 disease Diseases 0.000 claims description 44
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 44
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 44
- 125000000008 (C1-C10) alkyl group Chemical class 0.000 claims description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 40
- 239000002904 solvent Substances 0.000 claims description 40
- 150000002367 halogens Chemical class 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 38
- 238000011282 treatment Methods 0.000 claims description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 33
- 125000001424 substituent group Chemical group 0.000 claims description 29
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 27
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 26
- 150000002466 imines Chemical class 0.000 claims description 25
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 22
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 20
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 230000001404 mediated effect Effects 0.000 claims description 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
- 206010040070 Septic Shock Diseases 0.000 claims description 16
- 208000014674 injury Diseases 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 230000008569 process Effects 0.000 claims description 16
- 125000003107 substituted aryl group Chemical group 0.000 claims description 16
- 208000027418 Wounds and injury Diseases 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 14
- 230000006378 damage Effects 0.000 claims description 14
- 239000001301 oxygen Substances 0.000 claims description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 13
- 101150020251 NR13 gene Proteins 0.000 claims description 12
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 9
- 108010084680 Heterogeneous-Nuclear Ribonucleoprotein K Proteins 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 102100023482 Mitogen-activated protein kinase 14 Human genes 0.000 claims description 9
- 229910017711 NHRa Inorganic materials 0.000 claims description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 9
- 150000003141 primary amines Chemical class 0.000 claims description 9
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 8
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 8
- 206010040047 Sepsis Diseases 0.000 claims description 8
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 8
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 8
- 239000002243 precursor Substances 0.000 claims description 8
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 206010014824 Endotoxic shock Diseases 0.000 claims description 6
- 201000005569 Gout Diseases 0.000 claims description 6
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 6
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
- 206010044248 Toxic shock syndrome Diseases 0.000 claims description 6
- 231100000650 Toxic shock syndrome Toxicity 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 239000003153 chemical reaction reagent Substances 0.000 claims description 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 6
- 201000008482 osteoarthritis Diseases 0.000 claims description 6
- 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 5
- FTVFPPFZRRKJIH-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-4-amine Chemical compound CC1(C)CC(N)CC(C)(C)N1 FTVFPPFZRRKJIH-UHFFFAOYSA-N 0.000 claims description 5
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 5
- 125000006374 C2-C10 alkenyl group Chemical class 0.000 claims description 5
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 5
- 206010063837 Reperfusion injury Diseases 0.000 claims description 5
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 5
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 5
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 5
- 150000001768 cations Chemical class 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- XFXPMWWXUTWYJX-UHFFFAOYSA-N isonitrile group Chemical group N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 5
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 claims description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims description 4
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 4
- UHVAZVWTFCJNPH-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-3-piperidin-4-ylimidazol-4-yl]-n-phenylpyridin-2-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=C(NC=3C=CC=CC=3)N=CC=2)N(C2CCNCC2)C=N1 UHVAZVWTFCJNPH-UHFFFAOYSA-N 0.000 claims description 4
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims description 4
- 206010063094 Cerebral malaria Diseases 0.000 claims description 4
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 4
- 208000011231 Crohn disease Diseases 0.000 claims description 4
- 206010018634 Gouty Arthritis Diseases 0.000 claims description 4
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 4
- 201000004681 Psoriasis Diseases 0.000 claims description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 4
- 101100311330 Schizosaccharomyces pombe (strain 972 / ATCC 24843) uap56 gene Proteins 0.000 claims description 4
- 201000010001 Silicosis Diseases 0.000 claims description 4
- 208000006011 Stroke Diseases 0.000 claims description 4
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 125000003435 aroyl group Chemical group 0.000 claims description 4
- 230000002917 arthritic effect Effects 0.000 claims description 4
- 208000019664 bone resorption disease Diseases 0.000 claims description 4
- 230000001684 chronic effect Effects 0.000 claims description 4
- 239000007943 implant Substances 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 230000002685 pulmonary effect Effects 0.000 claims description 4
- 201000003651 pulmonary sarcoidosis Diseases 0.000 claims description 4
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
- 230000036303 septic shock Effects 0.000 claims description 4
- 101150018444 sub2 gene Proteins 0.000 claims description 4
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 4
- 229930192474 thiophene Natural products 0.000 claims description 4
- 150000003852 triazoles Chemical class 0.000 claims description 4
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 3
- 125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 3
- LKIOISBDXPXOKL-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-3-(1-methylpiperidin-4-yl)imidazol-4-yl]-n-(thian-4-yl)pyrimidin-2-amine Chemical compound C1CN(C)CCC1N1C(C=2N=C(NC3CCSCC3)N=CC=2)=C(C=2C=CC(F)=CC=2)N=C1 LKIOISBDXPXOKL-UHFFFAOYSA-N 0.000 claims description 3
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 claims description 3
- 208000001132 Osteoporosis Diseases 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 230000018044 dehydration Effects 0.000 claims description 3
- 238000006297 dehydration reaction Methods 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 125000004923 naphthylmethyl group Chemical class C1(=CC=CC2=CC=CC=C12)C* 0.000 claims description 3
- 150000003053 piperidines Chemical class 0.000 claims description 3
- 229960005235 piperonyl butoxide Drugs 0.000 claims description 3
- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 claims description 3
- 125000006239 protecting group Chemical group 0.000 claims description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
- 125000004632 tetrahydrothiopyranyl group Chemical class S1C(CCCC1)* 0.000 claims description 3
- OJBGEOXGUGYQKZ-UHFFFAOYSA-N 2-[[4-(4-fluorophenyl)-4-[1-(1-methylpiperidin-4-yl)imidazol-2-yl]-1h-pyrimidin-5-yl]amino]ethanol Chemical compound C1CN(C)CCC1N1C(C2(C(=CN=CN2)NCCO)C=2C=CC(F)=CC=2)=NC=C1 OJBGEOXGUGYQKZ-UHFFFAOYSA-N 0.000 claims description 2
- BQQCFBWHNKUAEA-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-3-piperidin-4-ylimidazol-4-yl]-n-(3-imidazol-1-ylpropyl)pyrimidin-2-amine Chemical compound C1=CC(F)=CC=C1C1=C(C=2N=C(NCCCN3C=NC=C3)N=CC=2)N(C2CCNCC2)C=N1 BQQCFBWHNKUAEA-UHFFFAOYSA-N 0.000 claims description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 101100295738 Gallus gallus COR3 gene Proteins 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 238000010952 in-situ formation Methods 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 2
- ZTSJPQOIAARTDL-UHFFFAOYSA-N n-chloro-2-(1h-indol-3-yl)ethanamine Chemical class C1=CC=C2C(CCNCl)=CNC2=C1 ZTSJPQOIAARTDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004546 quinazolin-4-yl group Chemical group N1=CN=C(C2=CC=CC=C12)* 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 208000037803 restenosis Diseases 0.000 claims description 2
- RKMGAJGJIURJSJ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidine Chemical compound CC1(C)CCCC(C)(C)N1 RKMGAJGJIURJSJ-UHFFFAOYSA-N 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- NZVZVGPYTICZBZ-UHFFFAOYSA-N 1-benzylpiperidine Chemical compound C=1C=CC=CC=1CN1CCCCC1 NZVZVGPYTICZBZ-UHFFFAOYSA-N 0.000 claims 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 claims 1
- 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 45
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- 239000003112 inhibitor Substances 0.000 abstract description 8
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- 102000000589 Interleukin-1 Human genes 0.000 description 40
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- GACUCTNCAUTQPH-UHFFFAOYSA-N 2-methylpyrimidine-4-carbothialdehyde Chemical compound CC1=NC=CC(C=S)=N1 GACUCTNCAUTQPH-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
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Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
-
- 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
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- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Cardiology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Heart & Thoracic Surgery (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Pulmonology (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Epoxy Resins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US47339695A | 1995-06-07 | 1995-06-07 | |
| US63677996A | 1996-04-19 | 1996-04-19 | |
| PCT/US1996/010039 WO1996040143A1 (en) | 1995-06-07 | 1996-06-07 | Imidazole compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69626513D1 DE69626513D1 (en) | 2003-04-10 |
| DE69626513T2 true DE69626513T2 (de) | 2003-12-24 |
Family
ID=27044121
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69626513T Expired - Fee Related DE69626513T2 (de) | 1995-06-07 | 1996-06-07 | Imidazolverbindungen |
Country Status (24)
| Country | Link |
|---|---|
| US (2) | US5658903A (enExample) |
| EP (2) | EP0831830B1 (enExample) |
| JP (1) | JPH11513017A (enExample) |
| KR (1) | KR19990022574A (enExample) |
| CN (1) | CN1130358C (enExample) |
| AT (1) | ATE233561T1 (enExample) |
| BR (1) | BR9608591A (enExample) |
| CA (1) | CA2223533A1 (enExample) |
| CZ (1) | CZ392597A3 (enExample) |
| DE (1) | DE69626513T2 (enExample) |
| DZ (1) | DZ2043A1 (enExample) |
| ES (1) | ES2194106T3 (enExample) |
| HU (1) | HUP9802259A3 (enExample) |
| IL (1) | IL118544A (enExample) |
| IN (1) | IN186434B (enExample) |
| MA (1) | MA24242A1 (enExample) |
| MY (1) | MY114014A (enExample) |
| NO (1) | NO975716L (enExample) |
| NZ (1) | NZ311403A (enExample) |
| PE (1) | PE7798A1 (enExample) |
| PL (1) | PL185515B1 (enExample) |
| TR (1) | TR199701574T2 (enExample) |
| TW (1) | TW442481B (enExample) |
| WO (1) | WO1996040143A1 (enExample) |
Families Citing this family (197)
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| US5916891A (en) | 1992-01-13 | 1999-06-29 | Smithkline Beecham Corporation | Pyrimidinyl imidazoles |
| EP0802908A4 (en) * | 1995-01-12 | 2001-04-11 | Smithkline Beecham Corp | NEW CONNECTIONS |
| US5739143A (en) * | 1995-06-07 | 1998-04-14 | Smithkline Beecham Corporation | Imidazole compounds and compositions |
| US5658903A (en) | 1995-06-07 | 1997-08-19 | Smithkline Beecham Corporation | Imidazole compounds, compositions and use |
| US6369068B1 (en) | 1995-06-07 | 2002-04-09 | Smithkline Beecham Corporation | Amino substituted pyrimidine containing compounds |
| ZA9610687B (en) * | 1995-12-22 | 1997-09-29 | Smithkline Beecham Corp | Novel synthesis. |
| US5977103A (en) * | 1996-01-11 | 1999-11-02 | Smithkline Beecham Corporation | Substituted imidazole compounds |
| US6046208A (en) * | 1996-01-11 | 2000-04-04 | Smithkline Beecham Corporation | Substituted imidazole compounds |
| AP9700912A0 (en) * | 1996-01-11 | 1997-01-31 | Smithkline Beecham Corp | Novel cycloalkyl substituted imidazoles |
| ZA97175B (en) * | 1996-01-11 | 1997-11-04 | Smithkline Beecham Corp | Novel substituted imidazole compounds. |
| JP2000507224A (ja) * | 1996-03-08 | 2000-06-13 | スミスクライン・ビーチャム・コーポレイション | Ｃｓａｉｄ化合物の血管形成の抑制物質としての使用 |
| JP2000507558A (ja) * | 1996-03-25 | 2000-06-20 | スミスクライン・ビーチャム・コーポレイション | Ｃｎｓ損傷についての新規な治療 |
| JP2000507545A (ja) * | 1996-03-25 | 2000-06-20 | スミスクライン・ビーチャム・コーポレイション | Ｃｎｓ損傷についての新規な治療 |
| EP0956018A4 (en) | 1996-08-21 | 2000-01-12 | Smithkline Beecham Corp | IMIDAZOLE COMPOUNDS, COMPOSITIONS CONTAINING THEM AND THEIR USE |
| AU5147598A (en) * | 1996-10-17 | 1998-05-11 | Smithkline Beecham Corporation | Methods for reversibly inhibiting myelopoiesis in mammalian tissue |
| ZA9711092B (en) * | 1996-12-11 | 1999-07-22 | Smithkline Beecham Corp | Novel compounds. |
| US6548512B1 (en) | 1996-12-23 | 2003-04-15 | Bristol-Myers Squibb Pharma Company | Nitrogen containing heteroaromatics as factor Xa inhibitors |
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| US6514977B1 (en) | 1997-05-22 | 2003-02-04 | G.D. Searle & Company | Substituted pyrazoles as p38 kinase inhibitors |
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| WO1998057966A1 (en) | 1997-06-19 | 1998-12-23 | Smithkline Beecham Corporation | Novel aryloxy substituted pyrimidine imidazole compounds |
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| TW517055B (en) | 1997-07-02 | 2003-01-11 | Smithkline Beecham Corp | Novel substituted imidazole compounds |
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| US6251914B1 (en) | 1997-07-02 | 2001-06-26 | Smithkline Beecham Corporation | Cycloalkyl substituted imidazoles |
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| BR9814961A (pt) * | 1997-11-14 | 2000-10-03 | Sankyo Co | Composto ou um sal ou derivado deste farmacologicamente aceitáveis, e, medicamentos antiinflamatório, para prevenção ou tratamento de reumatismo crÈnico, e para prevenção ou tratamento de osteoartrite |
| US6335340B1 (en) | 1997-12-19 | 2002-01-01 | Smithkline Beecham Corporation | compounds of heteroaryl substituted imidazole, their pharmaceutical compositons and uses |
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| KR20010025087A (ko) | 1998-05-22 | 2001-03-26 | 스튜어트 알. 수터 | 신규한 2-알킬 치환된 이미다졸 화합물 |
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| AU5438299A (en) | 1998-08-29 | 2000-03-21 | Astrazeneca Ab | Pyrimidine compounds |
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| JP2002528506A (ja) * | 1998-11-04 | 2002-09-03 | スミスクライン・ビーチャム・コーポレイション | ピリジン−４−イルまたはピリミジン−４−イル置換ピラジン |
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