TW480251B - Procedure for producing formylimidazoles - Google Patents
Procedure for producing formylimidazoles Download PDFInfo
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- TW480251B TW480251B TW087118818A TW87118818A TW480251B TW 480251 B TW480251 B TW 480251B TW 087118818 A TW087118818 A TW 087118818A TW 87118818 A TW87118818 A TW 87118818A TW 480251 B TW480251 B TW 480251B
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- catalytic oxidation
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- 238000000034 method Methods 0.000 title claims abstract description 11
- 230000003197 catalytic effect Effects 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 7
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 229910000510 noble metal Inorganic materials 0.000 claims description 5
- 230000003647 oxidation Effects 0.000 claims description 5
- 238000011049 filling Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 230000002079 cooperative effect Effects 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims 1
- 239000013589 supplement Substances 0.000 claims 1
- 150000002978 peroxides Chemical class 0.000 abstract description 5
- ZOMATQMEHRJKLO-UHFFFAOYSA-N 1h-imidazol-2-ylmethanol Chemical class OCC1=NC=CN1 ZOMATQMEHRJKLO-UHFFFAOYSA-N 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 2
- 239000013067 intermediate product Substances 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
- 239000010970 precious metal Substances 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
- JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- -1 hydroxyfluorimidazole Chemical group 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 210000003296 saliva Anatomy 0.000 description 2
- AKUNSTOMHUXJOZ-UHFFFAOYSA-N 1-hydroperoxybutane Chemical compound CCCCOO AKUNSTOMHUXJOZ-UHFFFAOYSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NRZUIOKXURFYHV-UHFFFAOYSA-N C(CCC)C1=C(C=2CC3=CC=CC(=C3C2C=C1)C)C=1N(C=CN1)CC1=CC=C(C(=O)O)C=C1 Chemical compound C(CCC)C1=C(C=2CC3=CC=CC(=C3C2C=C1)C)C=1N(C=CN1)CC1=CC=C(C(=O)O)C=C1 NRZUIOKXURFYHV-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
- 108010068370 Glutens Proteins 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229910052778 Plutonium Inorganic materials 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- CTYJTTYDINWPOU-UHFFFAOYSA-N benzenecarboperoxoic acid;methane Chemical compound C.OOC(=O)C1=CC=CC=C1 CTYJTTYDINWPOU-UHFFFAOYSA-N 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- YQHLDYVWEZKEOX-UHFFFAOYSA-N cumene hydroperoxide Chemical compound OOC(C)(C)C1=CC=CC=C1 YQHLDYVWEZKEOX-UHFFFAOYSA-N 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000021312 gluten Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910000449 hafnium oxide Inorganic materials 0.000 description 1
- WIHZLLGSGQNAGK-UHFFFAOYSA-N hafnium(4+);oxygen(2-) Chemical compound [O-2].[O-2].[Hf+4] WIHZLLGSGQNAGK-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000007857 hydrazones Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- OYEHPCDNVJXUIW-UHFFFAOYSA-N plutonium atom Chemical compound [Pu] OYEHPCDNVJXUIW-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- MWNQXXOSWHCCOZ-UHFFFAOYSA-L sodium;oxido carbonate Chemical compound [Na+].[O-]OC([O-])=O MWNQXXOSWHCCOZ-UHFFFAOYSA-L 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/62—Platinum group metals with gallium, indium, thallium, germanium, tin or lead
- B01J23/622—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead
- B01J23/628—Platinum group metals with gallium, indium, thallium, germanium, tin or lead with germanium, tin or lead with lead
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/54—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals combined with metals, oxides or hydroxides provided for in groups B01J23/02 - B01J23/36
- B01J23/56—Platinum group metals
- B01J23/64—Platinum group metals with arsenic, antimony, bismuth, vanadium, niobium, tantalum, polonium, chromium, molybdenum, tungsten, manganese, technetium or rhenium
- B01J23/644—Arsenic, antimony or bismuth
- B01J23/6447—Bismuth
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Catalysts (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
Description
--------_Β7^ 五、發明説明（！） 本發明係關於一種製借下々 >Γ里表爾下式甲醯基咪唑類之新穎方 法，
其中，R1為烧基， 其係藉著下式羥基甲基味唾類 一蔡中曾砵|一1 備 製 而化 氧性化 催 的 (請先閲讀背面之注意事項再填寫本頁) r裝· pz^CH.OH 丫
、1T ττ m： -OOtt 經濟部中央標準局員工消費合作社印製
p -A I 其中，R1定義如前。 甲基味唾類為，例如，於製備製藥物質，例如， 利尿劑或抗高血壓藥時之重要中間產物（w〇_A_92/ 20651)。已知有多種製造甲醯基^米唾類的方法。於ch_ A 685496中揭示—種由經基咪錢催化性氧化為f醯 基咪唾類之方法’其係在貴金屬催化劑存在之下進行， 例如’翻鉍，始黑，於活性炭上之始或鈀，並吹入氧 -I ί 1 ί ! - -I ϋϋ · :紙張尺度ϋ用中國國家標格釐) 87453Α ,i - -- I - A7 B7
CH2〇H
五、發明説明（ 氣 因此本發明之目的在於提供一種既經濟又改良之製 備曱醢基ϋ米唾類的方法。 於本發明中，此目的可由申請專利範圍第丨項中所 疋義之方法得到解答，於申請專利範圍第丨項中，式π 之羥基曱基咪唑類
U 請 先 閱 讀 背 面 意 事 項 再i 本 頁 裝 訂 經濟部中央標準局員工消費合作社印製 其中’ R1定義如前， 係在一貴金屬催化劑及過氧化物存在之下，經催化性氧 化為下式之甲醯基咪唑類
OOH
f .¾) k . 一’ :厓,-aJ 其中R1定義如前 Μ氏張尺度適用中國國家標準（CNS ) A4祝格（2丨0><297公釐） 480251 A7 B7 經濟部中央標準局員工消費合作社印製 五 發明説明（3 ) R1之定義為氫或烷基，特別是具1至6個碳原子的 直鏈或分支烷基。尤其是甲基、乙基、丙基、異丙基、 丁基、異丁基、特丁基、戊基及其異構物和己基及其異 構物。R1之定義宜為丁基。 例如於 WO-A 92/20651 或於 E_F· Godefroi et al·， Trav. Chim. Recueil Pays, Bes. 1383(1972)中所載 明，羥基曱基咪唑類可容易的製備用作為起始化合物。 翻，把，姥或金可用作為貴金屬催化劑。該貴金屬 係適當的與作為第二組成份之金屬，例如鉍，鉛，鈽或 銦一起使用。較佳之催化劑為翻/絲或顧/錯。 該貴金屬催化劑係單獨使用或附在一載體上，例如 活性炭，二氧化矽，二氧化鋁，矽一二氧化鋁，氧化鍅 或二氧化鈦上使用。宜附在活性炭上使用。 附在活性炭上的貴金屬催化劑為商業可得，例如由 Degussa ° 附在載體上之貴金屬的適當百分比相對於載體物質 之0.1及15%重量間，宜在0.5及7%重量間。 該貴金屬催化劑之使用量宜為相對於羥基曱基咪唑 類之0.05至1.0莫耳％貴金屬，且使用量最好為相對於 羥基甲基咪唑類之0.1至0.4莫耳％貴金屬。 有機或無機過氧化物係用作為過氧化物。例如，適 合者為過氧化氫，過硼酸鹽，過碳酸鹽，特丁基化氧 氫，枯基過氧氫，過苯甲酸，間氣過苯甲酸，單過酞酸 請 閲 面· 之 注 意 事 項
本紙張尺度適用中國國家標準（CNS ) A4規格（210X 297公釐） 02 48 A7 B7 五、發明説明（4 ) 或過醋酸。 用於10%至30%水溶液之過氧化氫特別適合。 該催化性氧化反應適合於水，水一溶混性溶劑或其 混合物存在之下，於鹼性環境中進行。 最適合的水一溶混性溶劑為，例如醇類或具1至6 個碳原子之羧酸類或酮類，如丙酮或曱基乙基酮。 宜使用水及水一溶混性溶劑之混合物。在所使用的 水中適當的加入驗性氫氧化物，鹼性碳酸鹽或驗性醋酸 鹽而將之調整為鹼性被證明為有利的。鹼性氫氧化物的 較佳使用量為相對於式II羥基甲基咪唑之莫耳量比例 為1:0.05至5，宜為1:1至3。 該催化性氧化作用適合在20°C至120°C之溫度時進 行，宜為50°C至8〇°C溫度。 在標準過氧化物加藥時間2至3小時後，式I化合 物可在充足的第二反應時間後用標準方式單離出來。 產物係用適當結晶法及過濾法單離出來。所用的催 化劑可以使用多次而不會喪失活性。 經濟部中央標準局員工消費合作社印製 實例 實例1 4-[(2-丁基-5-甲醯基-1H-咪唑-1-基）甲基]苯甲酸之製備 於室溫時將9.5克（33毫莫耳）4-[(2-丁基-5_羥基甲 基-1H-咪唑-1-基）甲基]苯甲酸，40毫升水，10毫升甲 醇，4.2克（105毫莫耳)NaOH及0.92克於活性炭上之 -6- 本紙張尺度適用中國國家標準（CNS ) A4現格（210X297公釐） 4β0251
五、發明說明（
Rnf；哲 f 請 t 第 871 18818 號 t 7NI°^^ ) (請先閱讀背面之注意事項再填寫本頁) (Submitted on October 17, 2000) 50/o翻及5%麵(含60%水）置於一 100毫升燒瓶中並加熱 到60°c。於60°C時在60分鐘期將6.6克（39毫莫 耳）20% HP2水溶液加到這個懸浮液中且然後將此混合 物用HPLC轉化。再次於60分鐘期間加入20% 112〇2水 溶液。然後於20分鐘期間加入I·7克（1〇毫貪耳）2〇0/〇 H2〇2水溶液（轉化>90%)。將混合物冷卻至室溫。用 17.6宅升HC1(15%)酸化至ρΗ=6·0後，產物沈殿出來。 將之冷卻到2°C，過濾，用2 X 20毫升水清洗並於室溫 在15毫巴時乾燥，得到7.2克（70%)黃色的4-[(2-丁基一 5-曱醯基-1H-咪唑-1-基）甲基]苯曱酸（hplc含量為 95%) 〇
熔點：144-146°C ^-NMR (DMS0-d6 400 MHz) δ : 12.9(1 H, s)· 經濟部智慧財產局員工消費合作社印製 9·65(1Η，s); 7.94(1Η. s)； 7·90(2Η，d); 7.11(2H，d); 5·65(2Η，s); 2·63(2Η, t); _ 1·54(2Η，戊)； 1·36(2Η，己)； 〇·79(3Η，t) -7-
87453A 本，紙張尺度適用中國國家標準（CNS)A4規格（210 X 297公釐）
Claims (1)
- 480251 h修正.Η補充 A8 B8 C8 D8 口 1. 一種製備下式（I)曱醯基咪唑類的方法， 六、申請專利範圍 專利申請案第87118818號 ROC Patent Αρρίη. Νό. 87118818 修正之申請專利範圍中文本一附件一 Amended Claims in Chinese - Enel. I (民國90年8月（(7日送呈) (Submitted on August (f] , 2001)C〇〇H 其中，R1為C「C6-烷基， 其包括於為貴金屬催化劑之翻/祕催化劑或始/錯催化 劑的存在下及於20°C至120°C的溫度下，催化性氧 化通式（II)之羥基曱基咪唑類 (請先閲讀背面之注意事項再填寫本頁) Γ 經濟部中央標準局員工消費合作社印製 h9oh(Π) 其中，R1定義如前 87453B 本紙張尺度適用中國國家標準（CNS ) A4規格（210X297公釐）申凊專利範圍 其特徵為該催化性氧化係在過氧化氫的存在之下進 行。 •如申請專利範圍第丨項之方法，其中…為丁基。 3·如申請專利範圍第丨項之方法，其中，催化性氧化 係在水，水一溶混性溶劑，或其混合物存在之下， 於一驗性介質中進行。 4.:申請專利範圍帛3項之方法，其中，鹼性介質係 藉添加鹼性氫氧化物到反應混合物中而得到。 -----^--.----I --------訂---------線 (請先閱讀背面之注意事項再填寫本頁) 經濟部智慧財產局員工消費合作社印製 本紙張尺度適用中國國家標準（CNS)A4規格（21〇 χ 297公釐）
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH263897 | 1997-11-14 | ||
| CH273897 | 1997-11-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW480251B true TW480251B (en) | 2002-03-21 |
Family
ID=25691005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW087118818A TW480251B (en) | 1997-11-14 | 1999-02-09 | Procedure for producing formylimidazoles |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP1051401B1 (zh) |
| JP (1) | JP4418104B2 (zh) |
| KR (1) | KR100550204B1 (zh) |
| CN (1) | CN1285824A (zh) |
| AR (1) | AR016678A1 (zh) |
| AT (1) | ATE376544T1 (zh) |
| AU (1) | AU743105B2 (zh) |
| BR (1) | BR9814174A (zh) |
| CA (1) | CA2309856C (zh) |
| CY (1) | CY1108524T1 (zh) |
| DE (1) | DE69838624T2 (zh) |
| DK (1) | DK1051401T3 (zh) |
| ES (1) | ES2296348T3 (zh) |
| HU (1) | HUP0004950A3 (zh) |
| IL (1) | IL136026A0 (zh) |
| IN (1) | IN190803B (zh) |
| NO (1) | NO315466B1 (zh) |
| NZ (1) | NZ504337A (zh) |
| PL (1) | PL340497A1 (zh) |
| PT (1) | PT1051401E (zh) |
| SI (1) | SI1051401T1 (zh) |
| TR (1) | TR200001349T2 (zh) |
| TW (1) | TW480251B (zh) |
| WO (1) | WO1999025696A1 (zh) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY119854A (en) * | 1998-06-15 | 2005-07-29 | Lonza Ag | Procedure for producing formyl imidazoles |
| CN111978257A (zh) * | 2020-08-26 | 2020-11-24 | 武汉药明康德新药开发有限公司 | 含有醛基和羧基的1-甲基芳烃-1h-咪唑系列化合物的合成方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5336779A (en) * | 1992-10-08 | 1994-08-09 | Nippon Gohsei Kagaku Kogyo Kabushiki Kaisha | Method of producing formylimidazoles |
| KR100587187B1 (ko) * | 1997-10-29 | 2006-10-24 | 론자 아게 | 포르밀이미다졸의제조방법 |
-
1998
- 1998-11-10 HU HU0004950A patent/HUP0004950A3/hu unknown
- 1998-11-10 DK DK98956918T patent/DK1051401T3/da active
- 1998-11-10 CA CA002309856A patent/CA2309856C/en not_active Expired - Fee Related
- 1998-11-10 PL PL98340497A patent/PL340497A1/xx not_active Application Discontinuation
- 1998-11-10 CN CN98813092A patent/CN1285824A/zh active Pending
- 1998-11-10 AU AU13384/99A patent/AU743105B2/en not_active Ceased
- 1998-11-10 EP EP98956918A patent/EP1051401B1/en not_active Expired - Lifetime
- 1998-11-10 KR KR1020007005214A patent/KR100550204B1/ko not_active Expired - Fee Related
- 1998-11-10 SI SI9830898T patent/SI1051401T1/sl unknown
- 1998-11-10 BR BR9814174-0A patent/BR9814174A/pt not_active IP Right Cessation
- 1998-11-10 NZ NZ504337A patent/NZ504337A/en unknown
- 1998-11-10 DE DE69838624T patent/DE69838624T2/de not_active Expired - Lifetime
- 1998-11-10 JP JP2000521080A patent/JP4418104B2/ja not_active Expired - Fee Related
- 1998-11-10 TR TR2000/01349T patent/TR200001349T2/xx unknown
- 1998-11-10 AT AT98956918T patent/ATE376544T1/de not_active IP Right Cessation
- 1998-11-10 WO PCT/EP1998/007322 patent/WO1999025696A1/en not_active Ceased
- 1998-11-10 ES ES98956918T patent/ES2296348T3/es not_active Expired - Lifetime
- 1998-11-10 PT PT98956918T patent/PT1051401E/pt unknown
- 1998-11-10 IL IL13602698A patent/IL136026A0/xx not_active IP Right Cessation
- 1998-11-12 IN IN3380DE1998 patent/IN190803B/en unknown
- 1998-11-12 AR ARP980105725A patent/AR016678A1/es active IP Right Grant
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1999
- 1999-02-09 TW TW087118818A patent/TW480251B/zh not_active IP Right Cessation
-
2000
- 2000-05-12 NO NO20002476A patent/NO315466B1/no not_active IP Right Cessation
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2007
- 2007-12-18 CY CY20071101603T patent/CY1108524T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO20002476D0 (no) | 2000-05-12 |
| CN1285824A (zh) | 2001-02-28 |
| SI1051401T1 (sl) | 2008-06-30 |
| AR016678A1 (es) | 2001-07-25 |
| NO20002476L (no) | 2000-05-12 |
| TR200001349T2 (tr) | 2001-01-22 |
| HUP0004950A3 (en) | 2002-01-28 |
| ATE376544T1 (de) | 2007-11-15 |
| AU743105B2 (en) | 2002-01-17 |
| JP4418104B2 (ja) | 2010-02-17 |
| CA2309856A1 (en) | 1999-05-27 |
| HUP0004950A2 (hu) | 2001-11-28 |
| NZ504337A (en) | 2002-03-28 |
| PT1051401E (pt) | 2007-12-24 |
| HK1034064A1 (zh) | 2001-10-12 |
| CA2309856C (en) | 2009-05-19 |
| IL136026A0 (en) | 2001-05-20 |
| JP2001523668A (ja) | 2001-11-27 |
| DK1051401T3 (da) | 2007-12-27 |
| AU1338499A (en) | 1999-06-07 |
| CY1108524T1 (el) | 2014-04-09 |
| KR20010032089A (ko) | 2001-04-16 |
| WO1999025696A1 (en) | 1999-05-27 |
| BR9814174A (pt) | 2000-09-26 |
| NO315466B1 (no) | 2003-09-08 |
| KR100550204B1 (ko) | 2006-02-08 |
| DE69838624D1 (de) | 2007-12-06 |
| EP1051401B1 (en) | 2007-10-24 |
| ES2296348T3 (es) | 2008-04-16 |
| EP1051401A1 (en) | 2000-11-15 |
| DE69838624T2 (de) | 2008-07-24 |
| PL340497A1 (en) | 2001-02-12 |
| IN190803B (zh) | 2003-08-23 |
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