UA65572C2 - Substituted imidazoles, intermediate compounds for the preparation thereof, a method for the preparation of substituted imidazoles and a method for the treatment of inflammatory diseases - Google Patents

Substituted imidazoles, intermediate compounds for the preparation thereof, a method for the preparation of substituted imidazoles and a method for the treatment of inflammatory diseases Download PDF

Info

Publication number: UA65572C2
Authority: UA; Ukraine
Prior art keywords: group; alkyl; substituted; fluorophenyl; imidazole
Prior art date: 1997-04-24

Application number

UA99105811A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Ortho Mcneil Pharm Inc

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.)

1997-04-24

Filing date

1998-04-17

Publication date

2004-04-15

1998-04-17 Application filed by Ortho Mcneil Pharm Inc filed Critical Ortho Mcneil Pharm Inc

2004-04-15 Publication of UA65572C2 publication Critical patent/UA65572C2/uk

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 123
150000002460 imidazoles Chemical class 0.000 title claims abstract description 33
238000000034 method Methods 0.000 title claims description 22
208000027866 inflammatory disease Diseases 0.000 title claims description 4
238000002360 preparation method Methods 0.000 title description 5
102000004127 Cytokines Human genes 0.000 claims abstract description 21
108090000695 Cytokines Proteins 0.000 claims abstract description 21
239000000543 intermediate Substances 0.000 claims abstract description 19
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 17
201000010099 disease Diseases 0.000 claims abstract description 10
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 56
-1 vinylene, ethynylene Chemical group 0.000 claims description 44
125000001072 heteroaryl group Chemical group 0.000 claims description 35
229910052736 halogen Inorganic materials 0.000 claims description 34
150000002367 halogens Chemical class 0.000 claims description 34
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 29
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
150000003839 salts Chemical class 0.000 claims description 26
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
125000001424 substituent group Chemical group 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 16
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 12
239000000460 chlorine Substances 0.000 claims description 12
229910052740 iodine Inorganic materials 0.000 claims description 12
150000002825 nitriles Chemical class 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 11
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
125000003277 amino group Chemical group 0.000 claims description 11
125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 11
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 11
229910052794 bromium Inorganic materials 0.000 claims description 11
238000006243 chemical reaction Methods 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 11
229920002554 vinyl polymer Polymers 0.000 claims description 11
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
239000011630 iodine Substances 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 9
125000004429 atom Chemical group 0.000 claims description 9
125000006413 ring segment Chemical group 0.000 claims description 9
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
229910052763 palladium Inorganic materials 0.000 claims description 8
125000005544 phthalimido group Chemical group 0.000 claims description 8
239000007822 coupling agent Substances 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
125000002560 nitrile group Chemical group 0.000 claims description 6
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
206010003246 arthritis Diseases 0.000 claims description 5
125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
230000003993 interaction Effects 0.000 claims description 5
239000002904 solvent Substances 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
241000124008 Mammalia Species 0.000 claims description 4
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
150000007530 organic bases Chemical class 0.000 claims description 4
QSUSKMBNZQHHPA-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)-1-(3-phenylpropyl)-5-pyridin-4-ylimidazol-2-yl]but-3-yn-1-ol Chemical compound C=1C=CC=CC=1CCCN1C(C#CCCO)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 QSUSKMBNZQHHPA-UHFFFAOYSA-N 0.000 claims description 3
IMWNIKIDZJRIGK-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-2-iodo-3-(3-phenylpropyl)imidazol-4-yl]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)N(CCCC=2C=CC=CC=2)C(I)=N1 IMWNIKIDZJRIGK-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 2
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
QOERMZSCFCZYCO-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)-1-(3-phenylpropyl)-5-pyridin-4-ylimidazol-2-yl]-n,n-dimethylbut-3-yn-1-amine Chemical compound C=1C=CC=CC=1CCCN1C(C#CCCN(C)C)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 QOERMZSCFCZYCO-UHFFFAOYSA-N 0.000 claims description 2
ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims description 2
WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
125000003544 oxime group Chemical group 0.000 claims description 2
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 8
JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 2
YJYGOGWMDDTIIU-UHFFFAOYSA-N 3-[4-(4-fluorophenyl)-1-(3-phenylpropyl)-5-pyridin-4-ylimidazol-2-yl]prop-2-yn-1-ol Chemical compound C=1C=CC=CC=1CCCN1C(C#CCO)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 YJYGOGWMDDTIIU-UHFFFAOYSA-N 0.000 claims 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 claims 2
IHHLHKLBHIEAOK-UHFFFAOYSA-N 5-[4-(4-fluorophenyl)-1-(3-phenylpropyl)-5-pyridin-4-ylimidazol-2-yl]pent-4-yn-1-ol Chemical compound C=1C=CC=CC=1CCCN1C(C#CCCCO)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 IHHLHKLBHIEAOK-UHFFFAOYSA-N 0.000 claims 2
230000001419 dependent effect Effects 0.000 claims 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
125000006596 (C1-C3) alkylcarbonyloxy group Chemical group 0.000 claims 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
KDSQXPCPIDCOQN-UHFFFAOYSA-N 4-[2-(5-butylsulfanylpent-1-ynyl)-5-(4-fluorophenyl)-3-(3-phenylpropyl)imidazol-4-yl]pyridine Chemical compound C=1C=CC=CC=1CCCN1C(C#CCCCSCCCC)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 KDSQXPCPIDCOQN-UHFFFAOYSA-N 0.000 claims 1
XOJLNOCCMFAJPV-UHFFFAOYSA-N 4-[2-(5-butylsulfonylpent-1-ynyl)-5-(4-fluorophenyl)-3-(3-phenylpropyl)imidazol-4-yl]pyridine Chemical compound C=1C=CC=CC=1CCCN1C(C#CCCCS(=O)(=O)CCCC)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 XOJLNOCCMFAJPV-UHFFFAOYSA-N 0.000 claims 1
KHHGVCBMFUGWEG-UHFFFAOYSA-N 4-[2-(5-chloropent-1-ynyl)-5-(4-fluorophenyl)-3-(3-phenylpropyl)imidazol-4-yl]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)N(CCCC=2C=CC=CC=2)C(C#CCCCCl)=N1 KHHGVCBMFUGWEG-UHFFFAOYSA-N 0.000 claims 1
ADFYINPKHOEJJY-UHFFFAOYSA-N 4-[2-bromo-5-(4-fluorophenyl)-3-(3-phenylpropyl)imidazol-4-yl]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)N(CCCC=2C=CC=CC=2)C(Br)=N1 ADFYINPKHOEJJY-UHFFFAOYSA-N 0.000 claims 1
UOCMNXKXUYBJET-UHFFFAOYSA-N 4-[2-chloro-5-(4-fluorophenyl)-3-(3-phenylpropyl)imidazol-4-yl]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)N(CCCC=2C=CC=CC=2)C(Cl)=N1 UOCMNXKXUYBJET-UHFFFAOYSA-N 0.000 claims 1
ZCLLWLYRFGXXFY-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)-1-(3-phenylpropyl)-5-pyridin-4-ylimidazol-2-yl]but-3-ynyl acetate Chemical compound C=1C=CC=CC=1CCCN1C(C#CCCOC(=O)C)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 ZCLLWLYRFGXXFY-UHFFFAOYSA-N 0.000 claims 1
SUDNTPYBVHNXOT-UHFFFAOYSA-N 4-[4-(4-fluorophenyl)-1-(3-phenylpropyl)-5-pyridin-4-ylimidazol-2-yl]but-3-ynyl benzoate Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)N(CCCC=2C=CC=CC=2)C(C#CCCOC(=O)C=2C=CC=CC=2)=N1 SUDNTPYBVHNXOT-UHFFFAOYSA-N 0.000 claims 1
IOKBLNMQALUDJY-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-2-(5-phenylpent-1-ynyl)-3-(3-phenylpropyl)imidazol-4-yl]pyridine Chemical compound C1=CC(F)=CC=C1C1=C(C=2C=CN=CC=2)N(CCCC=2C=CC=CC=2)C(C#CCCCC=2C=CC=CC=2)=N1 IOKBLNMQALUDJY-UHFFFAOYSA-N 0.000 claims 1
CBHBNYVEBBXTJR-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-2-oct-1-ynyl-3-(3-phenylpropyl)imidazol-4-yl]pyridine Chemical compound C=1C=CC=CC=1CCCN1C(C#CCCCCCC)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 CBHBNYVEBBXTJR-UHFFFAOYSA-N 0.000 claims 1
JIXUXAXJWCADIY-UHFFFAOYSA-N 4-[5-(4-fluorophenyl)-2-pent-1-ynyl-3-(3-phenylpropyl)imidazol-4-yl]pyridine Chemical compound C=1C=CC=CC=1CCCN1C(C#CCCC)=NC(C=2C=CC(F)=CC=2)=C1C1=CC=NC=C1 JIXUXAXJWCADIY-UHFFFAOYSA-N 0.000 claims 1
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 1
238000010438 heat treatment Methods 0.000 claims 1
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 claims 1
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238000010992 reflux Methods 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
230000002757 inflammatory effect Effects 0.000 abstract description 9
238000004519 manufacturing process Methods 0.000 abstract description 9
238000012261 overproduction Methods 0.000 abstract description 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
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239000007787 solid Substances 0.000 description 23
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238000001819 mass spectrum Methods 0.000 description 14
238000012360 testing method Methods 0.000 description 14
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MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
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150000002431 hydrogen Chemical class 0.000 description 7
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LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
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Classifications

- C—CHEMISTRY; METALLURGY
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- 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
- A—HUMAN NECESSITIES
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- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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- 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
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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
- 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
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
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Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
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Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
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Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Rheumatology (AREA)
Physical Education & Sports Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Epidemiology (AREA)
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Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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UA99105811A 1997-04-24 1998-04-17 Substituted imidazoles, intermediate compounds for the preparation thereof, a method for the preparation of substituted imidazoles and a method for the treatment of inflammatory diseases UA65572C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US4425297P	1997-04-24	1997-04-24
PCT/US1998/007910 WO1998047892A1 (en)	1997-04-24	1998-04-17	Substituted imidazoles useful in the treatment of inflammatory diseases

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UA65572C2 true UA65572C2 (en)	2004-04-15

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UA99105811A UA65572C2 (en)	1997-04-24	1998-04-17	Substituted imidazoles, intermediate compounds for the preparation thereof, a method for the preparation of substituted imidazoles and a method for the treatment of inflammatory diseases

Country Status (24)

Country	Link
US (3)	US5965583A (no)
EP (1)	EP1028954B1 (no)
JP (1)	JP2001522357A (no)
KR (1)	KR100568438B1 (no)
CN (1)	CN1211381C (no)
AR (1)	AR012594A1 (no)
AT (1)	ATE244234T1 (no)
AU (1)	AU7138298A (no)
BR (1)	BR9808998A (no)
CA (1)	CA2297176A1 (no)
DE (1)	DE69816109T2 (no)
DK (1)	DK1028954T3 (no)
ES (1)	ES2202840T3 (no)
HU (1)	HUP0002842A3 (no)
IL (1)	IL132318A0 (no)
NO (1)	NO318937B1 (no)
NZ (1)	NZ500447A (no)
PL (1)	PL191111B1 (no)
PT (1)	PT1028954E (no)
RU (1)	RU2222534C2 (no)
TR (1)	TR199902622T2 (no)
UA (1)	UA65572C2 (no)
WO (1)	WO1998047892A1 (no)
ZA (1)	ZA983451B (no)

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1998
- 1998-04-17 US US09/062,304 patent/US5965583A/en not_active Expired - Lifetime
- 1998-04-17 CN CNB988045230A patent/CN1211381C/zh not_active Expired - Fee Related
- 1998-04-17 JP JP54623198A patent/JP2001522357A/ja not_active Withdrawn
- 1998-04-17 CA CA002297176A patent/CA2297176A1/en not_active Abandoned
- 1998-04-17 AU AU71382/98A patent/AU7138298A/en not_active Abandoned
- 1998-04-17 NZ NZ500447A patent/NZ500447A/en unknown
- 1998-04-17 PT PT98918463T patent/PT1028954E/pt unknown
- 1998-04-17 BR BR9808998-6A patent/BR9808998A/pt not_active Application Discontinuation
- 1998-04-17 IL IL13231898A patent/IL132318A0/xx not_active IP Right Cessation
- 1998-04-17 DE DE69816109T patent/DE69816109T2/de not_active Expired - Fee Related
- 1998-04-17 PL PL336758A patent/PL191111B1/pl not_active IP Right Cessation
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- 1998-04-17 RU RU99122164/04A patent/RU2222534C2/ru not_active IP Right Cessation
- 1998-04-17 WO PCT/US1998/007910 patent/WO1998047892A1/en not_active Ceased
- 1998-04-17 AT AT98918463T patent/ATE244234T1/de not_active IP Right Cessation
- 1998-04-17 TR TR1999/02622T patent/TR199902622T2/xx unknown
- 1998-04-17 ES ES98918463T patent/ES2202840T3/es not_active Expired - Lifetime
- 1998-04-17 UA UA99105811A patent/UA65572C2/uk unknown
- 1998-04-17 KR KR1019997009785A patent/KR100568438B1/ko not_active Expired - Fee Related
- 1998-04-17 EP EP98918463A patent/EP1028954B1/en not_active Expired - Lifetime
- 1998-04-17 DK DK98918463T patent/DK1028954T3/da active
- 1998-04-23 ZA ZA9803451A patent/ZA983451B/xx unknown
- 1998-04-23 AR ARP980101886A patent/AR012594A1/es not_active Application Discontinuation
1999
- 1999-04-20 US US09/295,156 patent/US6214830B1/en not_active Expired - Lifetime
- 1999-10-19 NO NO19995095A patent/NO318937B1/no unknown
2000
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Also Published As

Publication number	Publication date
EP1028954A1 (en)	2000-08-23
EP1028954B1 (en)	2003-07-02
KR100568438B1 (ko)	2006-04-07
PL191111B1 (pl)	2006-03-31
DK1028954T3 (da)	2003-10-27
NZ500447A (en)	2001-09-28
PL336758A1 (en)	2000-07-17
CA2297176A1 (en)	1998-10-29
AU7138298A (en)	1998-11-13
ES2202840T3 (es)	2004-04-01
BR9808998A (pt)	2000-08-08
CN1211381C (zh)	2005-07-20
PT1028954E (pt)	2003-11-28
WO1998047892A1 (en)	1998-10-29
ATE244234T1 (de)	2003-07-15
CN1253558A (zh)	2000-05-17
HUP0002842A3 (en)	2002-01-28
DE69816109D1 (de)	2003-08-07
RU2222534C2 (ru)	2004-01-27
HUP0002842A2 (hu)	2001-06-28
US6521655B1 (en)	2003-02-18
KR20010020204A (ko)	2001-03-15
IL132318A0 (en)	2001-03-19
AR012594A1 (es)	2000-11-08
NO318937B1 (no)	2005-05-30
NO995095D0 (no)	1999-10-19
JP2001522357A (ja)	2001-11-13
DE69816109T2 (de)	2004-04-22
US5965583A (en)	1999-10-12
ZA983451B (en)	1999-10-25
US6214830B1 (en)	2001-04-10
NO995095L (no)	1999-12-09
TR199902622T2 (xx)	2000-05-22

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