IL117807A - Use of a history of 3,1-Dihydro-1 (phenylalkyl) - 2H-imidazole - 2 On for the preparation of drugs, such new derivatives, the process for their preparation and the pharmaceutical preparations containing them - Google Patents

Use of a history of 3,1-Dihydro-1 (phenylalkyl) - 2H-imidazole - 2 On for the preparation of drugs, such new derivatives, the process for their preparation and the pharmaceutical preparations containing them

Info

Publication number: IL117807A
Authority: IL; Israel
Prior art keywords: substituted; alkyl; formula; aryl; hydrogen
Prior art date: 1995-04-06

Application number

IL11780796A

Other languages

English (en)

Hebrew (he)

Other versions

IL117807A0 (en

Original Assignee

Janssen Pharmaceutica Nv

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.)

1995-04-06

Filing date

1996-04-03

Publication date

2001-06-14

1996-04-03 Application filed by Janssen Pharmaceutica Nv filed Critical Janssen Pharmaceutica Nv

1996-08-04 Publication of IL117807A0 publication Critical patent/IL117807A0/xx

2001-06-14 Publication of IL117807A publication Critical patent/IL117807A/en

Links

239000003814 drug Substances 0.000 title claims abstract description 16
238000000034 method Methods 0.000 title claims description 23
239000008194 pharmaceutical composition Substances 0.000 title claims description 11
230000008569 process Effects 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title description 13
-1 bicyclo [2.2.1]-2-heptenyl Chemical group 0.000 claims abstract description 180
150000001875 compounds Chemical class 0.000 claims abstract description 174
239000001257 hydrogen Substances 0.000 claims abstract description 114
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 114
125000003118 aryl group Chemical group 0.000 claims abstract description 90
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 83
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 80
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 55
229910052757 nitrogen Chemical group 0.000 claims abstract description 42
229920006395 saturated elastomer Polymers 0.000 claims abstract description 40
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 38
229910052760 oxygen Inorganic materials 0.000 claims abstract description 38
239000001301 oxygen Substances 0.000 claims abstract description 38
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 37
125000002541 furyl group Chemical group 0.000 claims abstract description 37
229910052717 sulfur Inorganic materials 0.000 claims abstract description 37
239000011593 sulfur Chemical group 0.000 claims abstract description 37
125000001544 thienyl group Chemical group 0.000 claims abstract description 37
125000005842 heteroatom Chemical group 0.000 claims abstract description 36
125000004076 pyridyl group Chemical group 0.000 claims abstract description 36
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 35
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 33
125000003386 piperidinyl group Chemical group 0.000 claims abstract description 32
125000001424 substituent group Chemical group 0.000 claims abstract description 31
150000002431 hydrogen Chemical group 0.000 claims abstract description 30
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 29
239000002253 acid Substances 0.000 claims abstract description 29
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 29
150000003839 salts Chemical class 0.000 claims abstract description 27
125000004391 aryl sulfonyl group Chemical group 0.000 claims abstract description 26
125000004193 piperazinyl group Chemical group 0.000 claims abstract description 21
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 18
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
102000004127 Cytokines Human genes 0.000 claims abstract description 14
108090000695 Cytokines Proteins 0.000 claims abstract description 14
BVCRERJDOOBZOH-UHFFFAOYSA-N bicyclo[2.2.1]heptanyl Chemical group C1C[C+]2CC[C-]1C2 BVCRERJDOOBZOH-UHFFFAOYSA-N 0.000 claims abstract description 14
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 13
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims abstract description 13
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims abstract description 12
201000010099 disease Diseases 0.000 claims abstract description 12
125000002883 imidazolyl group Chemical group 0.000 claims abstract description 10
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract description 10
125000002757 morpholinyl group Chemical group 0.000 claims abstract description 10
125000002971 oxazolyl group Chemical group 0.000 claims abstract description 10
125000000335 thiazolyl group Chemical group 0.000 claims abstract description 9
241001465754 Metazoa Species 0.000 claims abstract description 8
230000002255 enzymatic effect Effects 0.000 claims abstract description 6
238000004519 manufacturing process Methods 0.000 claims abstract description 6
102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims abstract description 5
108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims abstract description 5
230000002159 abnormal effect Effects 0.000 claims abstract description 5
230000003197 catalytic effect Effects 0.000 claims abstract description 5
230000001627 detrimental effect Effects 0.000 claims abstract description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract 9
125000000815 N-oxide group Chemical group 0.000 claims abstract 2
239000000543 intermediate Substances 0.000 claims description 80
239000011541 reaction mixture Substances 0.000 claims description 41
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 20
238000006243 chemical reaction Methods 0.000 claims description 19
239000002585 base Substances 0.000 claims description 18
239000012442 inert solvent Substances 0.000 claims description 15
208000012657 Atopic disease Diseases 0.000 claims description 13
208000026935 allergic disease Diseases 0.000 claims description 13
125000004432 carbon atom Chemical group C* 0.000 claims description 11
230000000172 allergic effect Effects 0.000 claims description 10
208000027866 inflammatory disease Diseases 0.000 claims description 10
125000006239 protecting group Chemical group 0.000 claims description 9
125000000217 alkyl group Chemical group 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical class NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 5
239000003153 chemical reaction reagent Substances 0.000 claims description 5
239000003937 drug carrier Substances 0.000 claims description 5
238000006356 dehydrogenation reaction Methods 0.000 claims description 4
238000010511 deprotection reaction Methods 0.000 claims description 4
238000005984 hydrogenation reaction Methods 0.000 claims description 4
229910021645 metal ion Inorganic materials 0.000 claims description 3
QRXNFMNALVKMSM-UHFFFAOYSA-N 3-[[1-(3-cyclopentyloxy-4-methoxyphenyl)cyclopropyl]methyl]-1h-imidazol-2-one Chemical compound COC1=CC=C(C2(CN3C(NC=C3)=O)CC2)C=C1OC1CCCC1 QRXNFMNALVKMSM-UHFFFAOYSA-N 0.000 claims description 2
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 2
206010012438 Dermatitis atopic Diseases 0.000 claims description 2
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 2
238000007259 addition reaction Methods 0.000 claims description 2
239000003513 alkali Substances 0.000 claims description 2
201000008937 atopic dermatitis Diseases 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
239000012948 isocyanate Substances 0.000 claims description 2
150000002513 isocyanates Chemical class 0.000 claims description 2
125000001475 halogen functional group Chemical group 0.000 claims 11
125000004356 hydroxy functional group Chemical group O* 0.000 claims 8
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 2
125000003806 alkyl carbonyl amino group Chemical group 0.000 claims 1
238000005804 alkylation reaction Methods 0.000 claims 1
230000003301 hydrolyzing effect Effects 0.000 claims 1
150000002902 organometallic compounds Chemical class 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
125000005843 halogen group Chemical group 0.000 abstract description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 18
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 20
125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 11
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 abstract 3
125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 abstract 3
125000003545 alkoxy group Chemical group 0.000 abstract 3
125000003342 alkenyl group Chemical group 0.000 abstract 2
125000000008 (C1-C10) alkyl group Chemical group 0.000 abstract 1
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 1
125000004448 alkyl carbonyl group Chemical group 0.000 abstract 1
125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 abstract 1
239000000203 mixture Substances 0.000 description 106
239000002904 solvent Substances 0.000 description 66
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 56
239000000243 solution Substances 0.000 description 46
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 42
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
150000003254 radicals Chemical group 0.000 description 36
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 29
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 29
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 28
239000003480 eluent Substances 0.000 description 27
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 26
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 26
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 26
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 25
239000012044 organic layer Substances 0.000 description 25
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 24
239000000741 silica gel Substances 0.000 description 24
229910002027 silica gel Inorganic materials 0.000 description 24
108010037444 diisopropylglutathione ester Proteins 0.000 description 23
239000002244 precipitate Substances 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 22
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
239000003054 catalyst Substances 0.000 description 20
229940093499 ethyl acetate Drugs 0.000 description 19
235000019439 ethyl acetate Nutrition 0.000 description 19
238000003756 stirring Methods 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
229910052943 magnesium sulfate Inorganic materials 0.000 description 15
230000000694 effects Effects 0.000 description 14
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 14
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
210000004027 cell Anatomy 0.000 description 12
238000004440 column chromatography Methods 0.000 description 12
230000002401 inhibitory effect Effects 0.000 description 12
238000012360 testing method Methods 0.000 description 12
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
235000019441 ethanol Nutrition 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
230000005764 inhibitory process Effects 0.000 description 10
239000008213 purified water Substances 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
229910000069 nitrogen hydride Inorganic materials 0.000 description 9
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 8
239000007983 Tris buffer Substances 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 8
239000000725 suspension Substances 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
150000001204 N-oxides Chemical group 0.000 description 7
238000002156 mixing Methods 0.000 description 7
238000005055 short column chromatography Methods 0.000 description 7
239000003826 tablet Substances 0.000 description 7
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 7
229920002307 Dextran Polymers 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
239000007868 Raney catalyst Substances 0.000 description 6
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 6
229910000564 Raney nickel Inorganic materials 0.000 description 6
229960004132 diethyl ether Drugs 0.000 description 6
238000001727 in vivo Methods 0.000 description 6
229920000858 Cyclodextrin Polymers 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
239000004480 active ingredient Substances 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000000975 dye Substances 0.000 description 5
238000004128 high performance liquid chromatography Methods 0.000 description 5
238000000338 in vitro Methods 0.000 description 5
239000002674 ointment Substances 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
238000007363 ring formation reaction Methods 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 4
206010015866 Extravasation Diseases 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
241000699670 Mus sp. Species 0.000 description 4
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
229910021529 ammonia Inorganic materials 0.000 description 4
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
239000006071 cream Substances 0.000 description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
230000036251 extravasation Effects 0.000 description 4
229910052736 halogen Inorganic materials 0.000 description 4
150000002367 halogens Chemical class 0.000 description 4
BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
238000004811 liquid chromatography Methods 0.000 description 4
210000004698 lymphocyte Anatomy 0.000 description 4
GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
229910000104 sodium hydride Inorganic materials 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
UAYWVJHJZHQCIE-UHFFFAOYSA-L zinc iodide Chemical compound I[Zn]I UAYWVJHJZHQCIE-UHFFFAOYSA-L 0.000 description 4
PAAZPARNPHGIKF-UHFFFAOYSA-N 1,2-dibromoethane Chemical compound BrCCBr PAAZPARNPHGIKF-UHFFFAOYSA-N 0.000 description 3
QKWWDTYDYOFRJL-UHFFFAOYSA-N 2,2-dimethoxyethanamine Chemical compound COC(CN)OC QKWWDTYDYOFRJL-UHFFFAOYSA-N 0.000 description 3
208000030507 AIDS Diseases 0.000 description 3
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AHWALFGBDFAJAI-UHFFFAOYSA-N phenyl carbonochloridate Chemical compound ClC(=O)OC1=CC=CC=C1 AHWALFGBDFAJAI-UHFFFAOYSA-N 0.000 description 3
239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 3
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 3
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241000701447 unidentified baculovirus Species 0.000 description 3
VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 2
KOIFVFCAXJUKHG-UHFFFAOYSA-N 2-(3-cyclopentyloxy-4-methoxyphenyl)acetonitrile Chemical compound COC1=CC=C(CC#N)C=C1OC1CCCC1 KOIFVFCAXJUKHG-UHFFFAOYSA-N 0.000 description 2
QJGCOOJXRVRPQB-UHFFFAOYSA-N 2-chloro-1-(3-cyclopentyloxy-4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)CCl)C=C1OC1CCCC1 QJGCOOJXRVRPQB-UHFFFAOYSA-N 0.000 description 2
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UBYNPNBASJLDED-UHFFFAOYSA-N 3-[2-(3,4-dimethoxyphenyl)propyl]-4-methyl-1h-imidazol-2-one Chemical compound C1=C(OC)C(OC)=CC=C1C(C)CN1C(=O)NC=C1C UBYNPNBASJLDED-UHFFFAOYSA-N 0.000 description 2
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241000700199 Cavia porcellus Species 0.000 description 2
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229920000053 polysorbate 80 Polymers 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
235000015320 potassium carbonate Nutrition 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
239000000047 product Substances 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
230000002685 pulmonary effect Effects 0.000 description 1
201000003651 pulmonary sarcoidosis Diseases 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
238000011002 quantification Methods 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
230000009467 reduction Effects 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000004648 relaxation of smooth muscle Effects 0.000 description 1
QEVHRUUCFGRFIF-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C(C5=CC=C(OC)C=C5N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 QEVHRUUCFGRFIF-MDEJGZGSSA-N 0.000 description 1
238000012552 review Methods 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
231100000241 scar Toxicity 0.000 description 1
230000036303 septic shock Effects 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
210000000329 smooth muscle myocyte Anatomy 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229960001407 sodium bicarbonate Drugs 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
238000002415 sodium dodecyl sulfate polyacrylamide gel electrophoresis Methods 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 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
229940075554 sorbate Drugs 0.000 description 1
239000001587 sorbitan monostearate Substances 0.000 description 1
235000011076 sorbitan monostearate Nutrition 0.000 description 1
229940035048 sorbitan monostearate Drugs 0.000 description 1
239000004544 spot-on Substances 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
230000008961 swelling Effects 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000007910 systemic administration Methods 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
229960003604 testosterone Drugs 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
230000009772 tissue formation Effects 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
229940100611 topical cream Drugs 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
229940042129 topical gel Drugs 0.000 description 1
239000003204 tranquilizing agent Substances 0.000 description 1
230000002936 tranquilizing effect Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000006433 tumor necrosis factor production Effects 0.000 description 1
230000008728 vascular permeability Effects 0.000 description 1
208000002003 vulvitis Diseases 0.000 description 1
235000012431 wafers Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
238000001262 western blot Methods 0.000 description 1
UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- 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]
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/36—One oxygen atom with hydrocarbon radicals, substituted by nitrogen atoms, attached to ring nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/70—One oxygen atom

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pulmonology (AREA)
Immunology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Dermatology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

IL11780796A 1995-04-06 1996-04-03 Use of a history of 3,1-Dihydro-1 (phenylalkyl) - 2H-imidazole - 2 On for the preparation of drugs, such new derivatives, the process for their preparation and the pharmaceutical preparations containing them IL117807A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP95200868		1995-04-06
EP95202898		1995-10-26

Publications (2)

Publication Number	Publication Date
IL117807A0 IL117807A0 (en)	1996-08-04
IL117807A true IL117807A (en)	2001-06-14

Family

ID=26139205

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL11780796A IL117807A (en)	1995-04-06	1996-04-03	Use of a history of 3,1-Dihydro-1 (phenylalkyl) - 2H-imidazole - 2 On for the preparation of drugs, such new derivatives, the process for their preparation and the pharmaceutical preparations containing them

Country Status (26)

Country	Link
US (2)	US5994376A (es)
EP (1)	EP0819122B1 (es)
JP (1)	JP4562101B2 (es)
KR (1)	KR100406628B1 (es)
CN (1)	CN1068591C (es)
AR (1)	AR002732A1 (es)
AT (1)	ATE214052T1 (es)
AU (1)	AU702947B2 (es)
CA (1)	CA2216653C (es)
CY (1)	CY2328B1 (es)
CZ (1)	CZ293127B6 (es)
DE (1)	DE69619661T2 (es)
DK (1)	DK0819122T3 (es)
ES (1)	ES2174064T3 (es)
HR (1)	HRP960155A2 (es)
HU (1)	HU223324B1 (es)
IL (1)	IL117807A (es)
MX (1)	MX9707652A (es)
MY (1)	MY119254A (es)
NO (1)	NO314339B1 (es)
NZ (1)	NZ304877A (es)
PL (1)	PL187375B1 (es)
PT (1)	PT819122E (es)
SI (1)	SI0819122T1 (es)
TW (1)	TW332201B (es)
WO (1)	WO1996031485A1 (es)

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US5703098A (en) *	1994-12-30	1997-12-30	Celgene Corporation	Immunotherapeutic imides/amides
TW332201B (en)	1995-04-06	1998-05-21	Janssen Pharmaceutica Nv	1,3-Dihydro-1-(phenylalkyl)-2H-imidazol-2-one derivatives
UA62939C2 (uk) *	1996-10-02	2004-01-15	Янссен Фармацевтика Н.В.	Похідне 2-ціаноіміноімідазолу, фармацевтична композиція та спосіб одержання сполуки
WO1999002504A1 (en)	1997-07-10	1999-01-21	Janssen Pharmaceutica N.V.	6-azauracil derivatives as il-5 inhibitors
US6017926A (en) *	1997-12-17	2000-01-25	Merck & Co., Inc.	Integrin receptor antagonists
SK284468B6 (sk) *	1998-04-01	2005-04-01	Janssen Pharmaceutica N. V.	Pyridínový derivát, spôsob jeho prípravy a použitie, kompozícia s jeho obsahom a spôsob jej prípravy
EP1071645A4 (en) *	1998-04-14	2003-04-02	Smithkline Beecham Corp	COMPOUNDS INHIBITING ISOENZYME PHOSPHODIESTERASE 4 (PDE 4)
US6172118B1 (en) *	1998-04-14	2001-01-09	Smithkline Beecham Corporation	Compounds
ES2198980T3 (es) *	1998-11-23	2004-02-01	Janssen Pharmaceutica N.V.	Derivados de 6-azauralico inhibidores de il-5.
CA2354511A1 (en)	1998-12-18	2000-06-29	Janssen Pharmaceutica N.V.	Il-5 inhibiting 6-azauracil derivatives
EP1322310A4 (en) *	2000-09-13	2004-09-15	Merck & Co Inc	ALPHA-V integrin receptor Antagonist
WO2002094320A1 (en)	2001-05-23	2002-11-28	Tanabe Seiyaku Co., Ltd.	Therapeutic compositions for repairing chondropathy
WO2002094321A1 (en) *	2001-05-23	2002-11-28	Tanabe Seiyaku Co., Ltd.	Compositions for promoting healing of bone fracture
US6706739B2 (en) *	2001-08-21	2004-03-16	National Health Research Institute	Imidazolidinone compounds
SE0200667D0 (sv) *	2002-03-05	2002-03-05	A & Science Invest Ab	Novel use of cytokine inhibitors
GB0326407D0 (en) *	2003-11-12	2003-12-17	Glaxo Group Ltd	Chemical compounds
GB0412865D0 (en) *	2004-06-09	2004-07-14	Glaxo Group Ltd	Chemical compounds
CA2572898C (en) *	2004-07-05	2010-04-20	Dong Wha Pharmaceutical Ind. Co., Ltd.	Composition for the prevention and treatment of allergic inflammatory disease
AR057455A1 (es) *	2005-07-22	2007-12-05	Merck & Co Inc	Inhibidores de la transcriptasa reversa de vih y composicion farmaceutica
EP1987009A1 (en) *	2006-01-30	2008-11-05	Euro-Celtique S.A.	Cyclourea compounds as calcium channel blockers
EP1834953A1 (en)	2006-03-14	2007-09-19	Ranbaxy Laboratories Limited	Tetrahydropyrane derivatives as 5-lipoxygenase inhibitors
US7390772B2 (en) *	2006-05-18	2008-06-24	International Flavor & Fragrances Inc.	1-phenyl-spiro[2.5]octane-1-carbonitrile analogues their use in fragrance formulations
WO2008157425A2 (en) *	2007-06-14	2008-12-24	The Regents Of The University Of California	Compounds for inhibiting protein aggregation, and methods for making and using them
NZ601967A (en) *	2010-03-12	2015-03-27	Omeros Corp	Pde10 inhibitors and related compositions and methods
NZ716462A (en)	2014-04-28	2017-11-24	Omeros Corp	Optically active pde10 inhibitor
NZ716494A (en)	2014-04-28	2017-07-28	Omeros Corp	Processes and intermediates for the preparation of a pde10 inhibitor
CN107530313A (zh)	2015-04-24	2018-01-02	奥默罗斯公司	Pde10抑制剂以及相关组合物和方法
WO2017079678A1 (en)	2015-11-04	2017-05-11	Omeros Corporation	Solid state forms of a pde10 inhibitor

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NL285394A (es) *	1961-11-17
US3184060A (en)	1963-02-13	1965-05-18	Owens Illinois Glass Co	Packaging tacky latex emulsion paints in containers manufactured from polyolefinic maerials
CA2095429A1 (en) *	1990-11-06	1992-05-07	Paul E. Bender	Imidazolidinone compounds
BR9307570A (pt) *	1992-12-02	1999-05-25	Pfizer	Diéteres de catecol como inibidores seletivos de pdeiv
TW263495B (es) *	1992-12-23	1995-11-21	Celltech Ltd
GB9304920D0 (en) *	1993-03-10	1993-04-28	Celltech Ltd	Chemical compounds
TW332201B (en)	1995-04-06	1998-05-21	Janssen Pharmaceutica Nv	1,3-Dihydro-1-(phenylalkyl)-2H-imidazol-2-one derivatives

1996
- 1996-03-22 TW TW085103447A patent/TW332201B/zh not_active IP Right Cessation
- 1996-03-28 AU AU52755/96A patent/AU702947B2/en not_active Expired
- 1996-03-28 HU HU9801575A patent/HU223324B1/hu active IP Right Grant
- 1996-03-28 AT AT96909150T patent/ATE214052T1/de active
- 1996-03-28 CN CN96193101A patent/CN1068591C/zh not_active Expired - Lifetime
- 1996-03-28 CZ CZ19973149A patent/CZ293127B6/cs not_active IP Right Cessation
- 1996-03-28 CA CA002216653A patent/CA2216653C/en not_active Expired - Lifetime
- 1996-03-28 EP EP96909150A patent/EP0819122B1/en not_active Expired - Lifetime
- 1996-03-28 PT PT96909150T patent/PT819122E/pt unknown
- 1996-03-28 US US08/930,296 patent/US5994376A/en not_active Expired - Lifetime
- 1996-03-28 PL PL96322654A patent/PL187375B1/pl unknown
- 1996-03-28 MX MX9707652A patent/MX9707652A/es unknown
- 1996-03-28 KR KR1019970706853A patent/KR100406628B1/ko not_active Expired - Lifetime
- 1996-03-28 WO PCT/EP1996/001394 patent/WO1996031485A1/en not_active Ceased
- 1996-03-28 SI SI9630434T patent/SI0819122T1/xx unknown
- 1996-03-28 NZ NZ304877A patent/NZ304877A/en not_active IP Right Cessation
- 1996-03-28 DK DK96909150T patent/DK0819122T3/da active
- 1996-03-28 DE DE69619661T patent/DE69619661T2/de not_active Expired - Lifetime
- 1996-03-28 ES ES96909150T patent/ES2174064T3/es not_active Expired - Lifetime
- 1996-03-28 JP JP52995996A patent/JP4562101B2/ja not_active Expired - Lifetime
- 1996-04-02 HR HR95202898.3A patent/HRP960155A2/hr not_active Application Discontinuation
- 1996-04-03 IL IL11780796A patent/IL117807A/en not_active IP Right Cessation
- 1996-04-03 AR ARP960102076A patent/AR002732A1/es active IP Right Grant
- 1996-04-05 MY MYPI96001300A patent/MY119254A/en unknown
1997
- 1997-10-06 NO NO19974602A patent/NO314339B1/no not_active IP Right Cessation
1999
- 1999-07-27 US US09/362,007 patent/US6403805B1/en not_active Expired - Lifetime
2002
- 2002-07-15 CY CY0200043A patent/CY2328B1/xx unknown

Also Published As

Publication number	Publication date
AU702947B2 (en)	1999-03-11
US5994376A (en)	1999-11-30
WO1996031485A1 (en)	1996-10-10
NO974602L (no)	1997-10-06
DE69619661T2 (de)	2002-10-31
CZ293127B6 (cs)	2004-02-18
JPH11503136A (ja)	1999-03-23
EP0819122B1 (en)	2002-03-06
JP4562101B2 (ja)	2010-10-13
MX9707652A (es)	1997-11-29
PT819122E (pt)	2002-08-30
PL187375B1 (pl)	2004-06-30
HRP960155A2 (en)	1997-10-31
AR002732A1 (es)	1998-04-29
CZ314997A3 (cs)	1998-12-16
ES2174064T3 (es)	2002-11-01
KR19980703449A (ko)	1998-11-05
CY2328B1 (en)	2004-02-06
CN1181072A (zh)	1998-05-06
HK1007880A1 (en)	1999-04-30
KR100406628B1 (ko)	2004-05-31
AU5275596A (en)	1996-10-23
NO974602D0 (no)	1997-10-06
US20020068830A1 (en)	2002-06-06
CA2216653C (en)	2009-05-26
MY119254A (en)	2005-04-30
CN1068591C (zh)	2001-07-18
TW332201B (en)	1998-05-21
HUP9801575A3 (en)	1999-03-01
DE69619661D1 (de)	2002-04-11
HUP9801575A2 (hu)	1999-01-28
NZ304877A (en)	1999-06-29
CA2216653A1 (en)	1996-10-10
HU223324B1 (hu)	2004-06-28
EP0819122A1 (en)	1998-01-21
NO314339B1 (no)	2003-03-10
SI0819122T1 (en)	2002-06-30
DK0819122T3 (da)	2002-07-01
US6403805B1 (en)	2002-06-11
ATE214052T1 (de)	2002-03-15
IL117807A0 (en)	1996-08-04
PL322654A1 (en)	1998-02-16

Legal Events

Date	Code	Title
2001-11-25	FF	Patent granted
2002-02-10	KB	Patent renewed
2002-05-23	KB	Patent renewed
2006-07-05	KB	Patent renewed
2010-10-31	KB	Patent renewed
2014-03-31	KB	Patent renewed
2016-11-30	EXP	Patent expired

Publication	Publication Date	Title
US6403805B1 (en)	2002-06-11	1,3-dihydro-1-(phenylalkyl)-2H-imidazol-2-one derivatves
EP0934280B1 (en)	2003-04-09	Pde iv inhibiting 2-cyanoiminoimidazole derivatives
EP0819123B1 (en)	2007-12-12	1,3-dihydro-1-(phenylalkenyl)-2h-imidazol-2-one derivatives having pde iv and cytokine inhibiting activity
EP0832071B1 (en)	2005-09-28	1,3-dihydro-2h-imidazol-2-one derivatives having pde iv and cytokinin inhibiting activity
US6656959B1 (en)	2003-12-02	PDE IV inhibiting pyridine derivatives
HK1007880B (en)	2002-07-05	1,3-dihydro-1-(phenylalkyl)-2h-imidazol-2-one derivatives having pdeiv and cytokine activity
AU697390C (en)	1999-07-22	1,3-dihydro-2h-imidazol-2-one derivatives having PDE IV and cytokinin inhibiting activity
HK1020344B (en)	2003-07-25	Pde iv inhibiting 2-cyanoiminoimidazole derivatives