DE69327890T2 - Verfahren zur Herstellung von 2-(un)substituierten 4-Alkylimidazolen - Google Patents
Verfahren zur Herstellung von 2-(un)substituierten 4-AlkylimidazolenInfo
- Publication number
- DE69327890T2 DE69327890T2 DE69327890T DE69327890T DE69327890T2 DE 69327890 T2 DE69327890 T2 DE 69327890T2 DE 69327890 T DE69327890 T DE 69327890T DE 69327890 T DE69327890 T DE 69327890T DE 69327890 T2 DE69327890 T2 DE 69327890T2
- Authority
- DE
- Germany
- Prior art keywords
- formula
- radical
- integer
- alkyl
- imidazoles
- 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
- 238000000034 method Methods 0.000 title claims description 19
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 aldehyde compound Chemical class 0.000 claims abstract description 29
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000002460 imidazoles Chemical class 0.000 claims abstract description 13
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 238000009833 condensation Methods 0.000 claims abstract description 5
- 230000005494 condensation Effects 0.000 claims abstract description 5
- 150000003254 radicals Chemical class 0.000 claims description 9
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000005041 acyloxyalkyl group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000011630 iodine Substances 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000003905 agrochemical Substances 0.000 abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 19
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 235000011114 ammonium hydroxide Nutrition 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 239000012043 crude product Substances 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- KJQOQMAGHMMDMV-UHFFFAOYSA-N 2,2-dichloro-3-methylbutanal Chemical compound CC(C)C(Cl)(Cl)C=O KJQOQMAGHMMDMV-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000005530 alkylenedioxy group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RGTYYGDMHXSGLS-UHFFFAOYSA-N 2,2-dichlorohexanal Chemical compound CCCCC(Cl)(Cl)C=O RGTYYGDMHXSGLS-UHFFFAOYSA-N 0.000 description 1
- FWNOUILZZKVNQJ-UHFFFAOYSA-N 2-methyl-5-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=CN=C(C)N1 FWNOUILZZKVNQJ-UHFFFAOYSA-N 0.000 description 1
- OIMQEZBKDKVPHU-UHFFFAOYSA-N 2-phenyl-5-propyl-1h-imidazole Chemical compound CCCC1=CNC(C=2C=CC=CC=2)=N1 OIMQEZBKDKVPHU-UHFFFAOYSA-N 0.000 description 1
- DRSZTATWOSZRAK-UHFFFAOYSA-N 3,4-dibromobutan-2-one Chemical compound CC(=O)C(Br)CBr DRSZTATWOSZRAK-UHFFFAOYSA-N 0.000 description 1
- YOTBOYFKPMRBAG-UHFFFAOYSA-N 5-butyl-1h-imidazole Chemical compound CCCCC1=CNC=N1 YOTBOYFKPMRBAG-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 239000002259 anti human immunodeficiency virus agent Substances 0.000 description 1
- 229940124411 anti-hiv antiviral agent Drugs 0.000 description 1
- 125000005129 aryl carbonyl group Chemical group 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- YEMKVBRHRNHHGE-UHFFFAOYSA-N n-methyl-1-(1-methylpyrrol-2-yl)methanamine Chemical compound CNCC1=CC=CN1C YEMKVBRHRNHHGE-UHFFFAOYSA-N 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 230000007096 poisonous effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000005425 toluyl group Chemical group 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
- C07D233/54—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
- C07D233/68—Halogen 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
-
- 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
- C07D233/56—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 only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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
- C07D401/04—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Radar Systems Or Details Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21907892 | 1992-08-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69327890D1 DE69327890D1 (de) | 2000-03-30 |
| DE69327890T2 true DE69327890T2 (de) | 2000-07-20 |
Family
ID=16729919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69327890T Expired - Fee Related DE69327890T2 (de) | 1992-08-18 | 1993-08-13 | Verfahren zur Herstellung von 2-(un)substituierten 4-Alkylimidazolen |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5312927A (enExample) |
| EP (1) | EP0585014B1 (enExample) |
| JP (1) | JP3393891B2 (enExample) |
| KR (1) | KR100244831B1 (enExample) |
| CN (1) | CN1032690C (enExample) |
| AT (1) | ATE189890T1 (enExample) |
| CA (1) | CA2104268C (enExample) |
| DE (1) | DE69327890T2 (enExample) |
| DK (1) | DK0585014T3 (enExample) |
| ES (1) | ES2145033T3 (enExample) |
| GR (1) | GR3032807T3 (enExample) |
| HU (1) | HU216973B (enExample) |
| PT (1) | PT585014E (enExample) |
| TW (1) | TW240223B (enExample) |
| ZA (1) | ZA936054B (enExample) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5646281A (en) * | 1990-12-28 | 1997-07-08 | Neurogen Corporation | Certain 4-piperidino- and piperazinomethyl-2-phenyl imidazole derivatives; dopamine receptor subtype specific ligands |
| US5681956A (en) * | 1990-12-28 | 1997-10-28 | Neurogen Corporation | 4-aryl substituted piperazinylmethyl phenylimidazole derivatives; a new class of dopamine receptor subtype specific ligands |
| US5646280A (en) * | 1990-12-28 | 1997-07-08 | Neurogen Corporation | Substituted 4-(alkyl, dialkyl) or cycloaklyl)aminomethyl 2-phenylimidazoes: dopamine receptor subtype specific ligands |
| US5633376A (en) * | 1990-12-28 | 1997-05-27 | Neurogen Corporation | Certain aminomethyl phenylimidazole derivatives; and 4-aryl substituted piperazinyl and piperidinylmethyl phenylimidazole derivatives; a new class of dopamine receptor subtype ligands |
| US5362334A (en) * | 1993-12-23 | 1994-11-08 | Macdermid, Incorporated | Composition and process for treatment of metallic surfaces |
| FR2717474B1 (fr) * | 1994-03-15 | 1996-06-21 | Hoechst France | Procédé de préparation d'acétals du formyl-2 imidazole. |
| CA2232467A1 (en) | 1997-03-20 | 1998-09-20 | Richard A. Glennon | Imidazoles with serotonin receptor binding activity |
| US6503935B1 (en) | 1998-08-07 | 2003-01-07 | Abbott Laboratories | Imidazoles and related compounds as α1A agonists |
| US6166205A (en) * | 1998-09-02 | 2000-12-26 | Neurogen Corporation | 2-Aryl-4-(1-[4-heteroaryl]piperazin-1-yl)methylimidazoles: dopamine . D.sub4 receptor subtype ligands |
| US7108834B2 (en) | 2004-10-14 | 2006-09-19 | Chuan Pan Huang | Device for producing negative ion fragrance |
| US9029408B2 (en) | 2008-06-16 | 2015-05-12 | Gtx, Inc. | Compounds for treatment of cancer |
| US9447049B2 (en) | 2010-03-01 | 2016-09-20 | University Of Tennessee Research Foundation | Compounds for treatment of cancer |
| PL3289876T3 (pl) | 2008-06-16 | 2022-11-21 | University Of Tennessee Research Foundation | Związki do leczenia nowotworu |
| EP3064204A1 (en) * | 2010-03-01 | 2016-09-07 | GTx, Inc. | Compounds for treatment of cancer |
| CN102199126B (zh) * | 2010-03-25 | 2013-06-05 | 中国石油化工股份有限公司 | 一种二烷基咪唑的制备方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7017486A (enExample) * | 1969-12-15 | 1971-06-17 | ||
| GB2068362B (en) * | 1980-01-25 | 1983-11-16 | Kodak Ltd | Preparation of imidazoles |
| DE3018458A1 (de) * | 1980-05-14 | 1982-01-21 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von 4-methylimidazolen |
| YU47834B (sr) * | 1989-08-10 | 1996-01-09 | Schering Agrochemical Limited | Azolni pesticid |
| AU1191292A (en) * | 1991-02-11 | 1992-09-07 | Schering Agrochemicals Limited | Imidazole pesticides |
-
1993
- 1993-08-12 JP JP20052393A patent/JP3393891B2/ja not_active Expired - Fee Related
- 1993-08-13 ES ES93306405T patent/ES2145033T3/es not_active Expired - Lifetime
- 1993-08-13 EP EP93306405A patent/EP0585014B1/en not_active Expired - Lifetime
- 1993-08-13 DE DE69327890T patent/DE69327890T2/de not_active Expired - Fee Related
- 1993-08-13 AT AT93306405T patent/ATE189890T1/de not_active IP Right Cessation
- 1993-08-13 PT PT93306405T patent/PT585014E/pt unknown
- 1993-08-13 DK DK93306405T patent/DK0585014T3/da active
- 1993-08-16 US US08/106,550 patent/US5312927A/en not_active Expired - Fee Related
- 1993-08-17 KR KR1019930015913A patent/KR100244831B1/ko not_active Expired - Fee Related
- 1993-08-17 CA CA002104268A patent/CA2104268C/en not_active Expired - Fee Related
- 1993-08-17 HU HU9302360A patent/HU216973B/hu not_active IP Right Cessation
- 1993-08-18 CN CN93118117A patent/CN1032690C/zh not_active Expired - Fee Related
- 1993-08-18 ZA ZA936054A patent/ZA936054B/xx unknown
- 1993-08-18 TW TW082106649A patent/TW240223B/zh active
-
2000
- 2000-02-29 GR GR20000400512T patent/GR3032807T3/el not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0585014A2 (en) | 1994-03-02 |
| KR940003938A (ko) | 1994-03-14 |
| PT585014E (pt) | 2000-06-30 |
| GR3032807T3 (en) | 2000-06-30 |
| HUT65121A (en) | 1994-04-28 |
| ZA936054B (en) | 1995-02-03 |
| HU216973B (hu) | 1999-10-28 |
| DK0585014T3 (da) | 2000-06-05 |
| DE69327890D1 (de) | 2000-03-30 |
| KR100244831B1 (ko) | 2000-03-02 |
| EP0585014B1 (en) | 2000-02-23 |
| US5312927A (en) | 1994-05-17 |
| TW240223B (enExample) | 1995-02-11 |
| CN1091130A (zh) | 1994-08-24 |
| JP3393891B2 (ja) | 2003-04-07 |
| JPH06116242A (ja) | 1994-04-26 |
| CA2104268C (en) | 2003-10-28 |
| HU9302360D0 (en) | 1993-11-29 |
| CN1032690C (zh) | 1996-09-04 |
| ATE189890T1 (de) | 2000-03-15 |
| CA2104268A1 (en) | 1994-02-19 |
| EP0585014A3 (en) | 1994-12-14 |
| ES2145033T3 (es) | 2000-07-01 |
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