JP4772780B2 - ５−カルボキシアルデヒド−２−３−ジヒドロベンゾオキセピン調製のための新規な１−メトキシ−２−フェニルエテン - Google Patents
５−カルボキシアルデヒド−２−３−ジヒドロベンゾオキセピン調製のための新規な１−メトキシ−２−フェニルエテン Download PDFInfo
- Publication number
- JP4772780B2 JP4772780B2 JP2007509908A JP2007509908A JP4772780B2 JP 4772780 B2 JP4772780 B2 JP 4772780B2 JP 2007509908 A JP2007509908 A JP 2007509908A JP 2007509908 A JP2007509908 A JP 2007509908A JP 4772780 B2 JP4772780 B2 JP 4772780B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- formula
- group
- alkyl
- optionally
- 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
- 238000002360 preparation method Methods 0.000 title claims description 19
- CTHJQRHPNQEPAB-UHFFFAOYSA-N 2-methoxyethenylbenzene Chemical compound COC=CC1=CC=CC=C1 CTHJQRHPNQEPAB-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 129
- 238000000034 method Methods 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- -1 alkyl lithium Chemical compound 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 239000002585 base Substances 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 239000000203 mixture Substances 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 21
- 125000003545 alkoxy group Chemical group 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 15
- 150000004714 phosphonium salts Chemical class 0.000 claims description 13
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 12
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 9
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 claims description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 239000000010 aprotic solvent Substances 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 7
- 239000011574 phosphorus Substances 0.000 claims description 7
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims description 5
- 150000008041 alkali metal carbonates Chemical class 0.000 claims description 5
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 5
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 5
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000006652 (C3-C12) cycloalkyl group Chemical group 0.000 claims description 4
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 229910019093 NaOCl Inorganic materials 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004465 cycloalkenyloxy group Chemical group 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methyl-cyclopentane Natural products CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 6
- 239000003880 polar aprotic solvent Substances 0.000 claims 2
- 229910052744 lithium Inorganic materials 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 150000001299 aldehydes Chemical class 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- 238000007796 conventional method Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 125000003342 alkenyl group Chemical group 0.000 description 7
- FZHSPPYCNDYIKD-UHFFFAOYSA-N 5-methoxysalicylaldehyde Chemical compound COC1=CC=C(O)C(C=O)=C1 FZHSPPYCNDYIKD-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 5
- 230000002411 adverse Effects 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 239000012047 saturated solution Substances 0.000 description 5
- 238000006546 Horner-Wadsworth-Emmons reaction Methods 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000002798 polar solvent Substances 0.000 description 4
- LEHBURLTIWGHEM-UHFFFAOYSA-N pyridinium chlorochromate Chemical compound [O-][Cr](Cl)(=O)=O.C1=CC=[NH+]C=C1 LEHBURLTIWGHEM-UHFFFAOYSA-N 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 235000009518 sodium iodide Nutrition 0.000 description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 3
- NJXRYHRBEGYUPB-UHFFFAOYSA-N 3,3-dimethyl-2h-1-benzoxepine-5-carbaldehyde Chemical class O=CC1=CC(C)(C)COC2=CC=CC=C21 NJXRYHRBEGYUPB-UHFFFAOYSA-N 0.000 description 3
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001188 haloalkyl group Chemical group 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 125000006413 ring segment Chemical group 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
- AHWAGLZCTFNKBG-UHFFFAOYSA-N 3h-1-benzoxepin-2-one Chemical compound O1C(=O)CC=CC2=CC=CC=C21 AHWAGLZCTFNKBG-UHFFFAOYSA-N 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- FJTDJJRLZXTYOW-UHFFFAOYSA-N 7-methoxy-3,3-dimethyl-2h-1-benzoxepine-5-carbaldehyde Chemical compound O1CC(C)(C)C=C(C=O)C2=CC(OC)=CC=C21 FJTDJJRLZXTYOW-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- AMIMRNSIRUDHCM-UHFFFAOYSA-N Isopropylaldehyde Chemical compound CC(C)C=O AMIMRNSIRUDHCM-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000007239 Wittig reaction Methods 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000012300 argon atmosphere Substances 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 2
- 229910000105 potassium hydride Inorganic materials 0.000 description 2
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- 230000004224 protection Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000009466 transformation Effects 0.000 description 2
- 238000000844 transformation Methods 0.000 description 2
- IPOOOIBJQZVDCA-UHFFFAOYSA-N (1-hydroxy-2,2-dimethylpropyl) methanesulfonate Chemical compound CC(C)(C)C(O)OS(C)(=O)=O IPOOOIBJQZVDCA-UHFFFAOYSA-N 0.000 description 1
- ZVSNGVBYOIFXCY-UHFFFAOYSA-N (3,3-diethoxy-2,2-dimethylpropyl) methanesulfonate Chemical compound CCOC(OCC)C(C)(C)COS(C)(=O)=O ZVSNGVBYOIFXCY-UHFFFAOYSA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LWLAPDUEXHDCAE-UHFFFAOYSA-N 1-chloro-2,2-dimethylpropan-1-ol Chemical compound CC(C)(C)C(O)Cl LWLAPDUEXHDCAE-UHFFFAOYSA-N 0.000 description 1
- HFMOBKBIBPODDD-UHFFFAOYSA-N 2-(1,3-dioxolan-2-yl)-2-methylpropan-1-ol Chemical compound OCC(C)(C)C1OCCO1 HFMOBKBIBPODDD-UHFFFAOYSA-N 0.000 description 1
- HYUZJBRNTRHBER-UHFFFAOYSA-N 2-(3,3-diethoxy-2-methylpropoxy)-5-methoxybenzaldehyde Chemical compound CCOC(OCC)C(C)COC1=CC=C(OC)C=C1C=O HYUZJBRNTRHBER-UHFFFAOYSA-N 0.000 description 1
- UIWAGDBKYMFMLD-UHFFFAOYSA-N 2-[2-(1,3-dioxolan-2-yl)-2-methylpropoxy]-5-methoxybenzaldehyde Chemical compound O=CC1=CC(OC)=CC=C1OCC(C)(C)C1OCCO1 UIWAGDBKYMFMLD-UHFFFAOYSA-N 0.000 description 1
- 125000005979 2-naphthyloxy group Chemical group 0.000 description 1
- YFBAZNSOMSLRHA-UHFFFAOYSA-N 3,3-dimethyl-7-(trifluoromethyl)-2h-1-benzoxepine-5-carbaldehyde Chemical compound O=CC1=CC(C)(C)COC2=CC=C(C(F)(F)F)C=C21 YFBAZNSOMSLRHA-UHFFFAOYSA-N 0.000 description 1
- BNIGFKIAHYBVJF-UHFFFAOYSA-N 3,3-dimethyl-7-phenyl-2h-1-benzoxepine-5-carbaldehyde Chemical compound C1=C2C(C=O)=CC(C)(C)COC2=CC=C1C1=CC=CC=C1 BNIGFKIAHYBVJF-UHFFFAOYSA-N 0.000 description 1
- GBPJKCNNAPOFQL-UHFFFAOYSA-N 3-bromo-1,1-diethoxy-2,2-dimethylpropane Chemical compound CCOC(OCC)C(C)(C)CBr GBPJKCNNAPOFQL-UHFFFAOYSA-N 0.000 description 1
- KQOQXYPZBYTICM-UHFFFAOYSA-N 3-bromo-2,2-dimethylpropan-1-ol Chemical compound OCC(C)(C)CBr KQOQXYPZBYTICM-UHFFFAOYSA-N 0.000 description 1
- XMKISEFVBOLIHI-UHFFFAOYSA-N 3-chloro-1,1-diethoxy-2,2-dimethylpropane Chemical compound CCOC(OCC)C(C)(C)CCl XMKISEFVBOLIHI-UHFFFAOYSA-N 0.000 description 1
- CAZPRAORHCOIHC-UHFFFAOYSA-N 3-chloro-2,2-dimethylpropan-1-ol Chemical compound OCC(C)(C)CCl CAZPRAORHCOIHC-UHFFFAOYSA-N 0.000 description 1
- MYGGQSNCIKRMLN-UHFFFAOYSA-N 3-iodo-2,2-dimethylpropan-1-ol Chemical compound OCC(C)(C)CI MYGGQSNCIKRMLN-UHFFFAOYSA-N 0.000 description 1
- HXGFFRALJQMFCH-UHFFFAOYSA-N 3-iodo-2-methylbutanal Chemical compound CC(I)C(C)C=O HXGFFRALJQMFCH-UHFFFAOYSA-N 0.000 description 1
- NQVHRWFVWPPPJL-UHFFFAOYSA-N 7,8-dichloro-3,3-dimethyl-2h-1-benzoxepine-5-carbaldehyde Chemical compound O=CC1=CC(C)(C)COC2=CC(Cl)=C(Cl)C=C21 NQVHRWFVWPPPJL-UHFFFAOYSA-N 0.000 description 1
- LRUYDLUCMKVCIX-UHFFFAOYSA-N 7,8-dimethoxy-3,3-dimethyl-2h-1-benzoxepine-5-carbaldehyde Chemical compound O1CC(C)(C)C=C(C=O)C2=C1C=C(OC)C(OC)=C2 LRUYDLUCMKVCIX-UHFFFAOYSA-N 0.000 description 1
- NSCROSAISOHTDC-UHFFFAOYSA-N 7-(4-chlorobenzoyl)-3,3-dimethyl-2h-1-benzoxepine-5-carbaldehyde Chemical compound C1=C2C(C=O)=CC(C)(C)COC2=CC=C1C(=O)C1=CC=C(Cl)C=C1 NSCROSAISOHTDC-UHFFFAOYSA-N 0.000 description 1
- VXPBRJKXTSHXBL-UHFFFAOYSA-N 7-bromo-3,3-dimethyl-2h-1-benzoxepine-5-carbaldehyde Chemical compound O=CC1=CC(C)(C)COC2=CC=C(Br)C=C21 VXPBRJKXTSHXBL-UHFFFAOYSA-N 0.000 description 1
- NPJYCRDSDWGMQZ-UHFFFAOYSA-N 7-chloro-3,3-dimethyl-2h-1-benzoxepine-5-carbaldehyde Chemical compound O=CC1=CC(C)(C)COC2=CC=C(Cl)C=C21 NPJYCRDSDWGMQZ-UHFFFAOYSA-N 0.000 description 1
- OXKPNPDAPSWFFL-UHFFFAOYSA-N 7-fluoro-3,3-dimethyl-2h-1-benzoxepine-5-carbaldehyde Chemical compound O=CC1=CC(C)(C)COC2=CC=C(F)C=C21 OXKPNPDAPSWFFL-UHFFFAOYSA-N 0.000 description 1
- YDSRIAJGIXYFOQ-UHFFFAOYSA-N 8-chloro-7-fluoro-3,3-dimethyl-2h-1-benzoxepine-5-carbaldehyde Chemical compound O=CC1=CC(C)(C)COC2=CC(Cl)=C(F)C=C21 YDSRIAJGIXYFOQ-UHFFFAOYSA-N 0.000 description 1
- ASNIFYVGQKEYOM-UHFFFAOYSA-N 9-methoxy-3,3-dimethyl-2h-1-benzoxepine-5-carbaldehyde Chemical compound O1CC(C)(C)C=C(C=O)C2=C1C(OC)=CC=C2 ASNIFYVGQKEYOM-UHFFFAOYSA-N 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 208000032928 Dyslipidaemia Diseases 0.000 description 1
- 102000010029 Homer Scaffolding Proteins Human genes 0.000 description 1
- 208000017170 Lipid metabolism disease Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- NMWWBGCEALAKKT-UHFFFAOYSA-N [2-(1,3-dioxolan-2-yl)-2-methylpropyl] methanesulfonate Chemical compound CS(=O)(=O)OCC(C)(C)C1OCCO1 NMWWBGCEALAKKT-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 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
- 238000009835 boiling Methods 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical class [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([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
- 125000006547 cyclononyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([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
- 125000003493 decenyl group Chemical group [H]C([*])=C([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- SOCTUWSJJQCPFX-UHFFFAOYSA-N dichromate(2-) Chemical compound [O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O SOCTUWSJJQCPFX-UHFFFAOYSA-N 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-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
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000013067 intermediate product 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
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004370 n-butenyl group Chemical group [H]\C([H])=C(/[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 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
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
- C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
- C07C309/66—Methanesulfonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/313—Compounds having groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/30—Compounds having groups
- C07C43/315—Compounds having groups containing oxygen atoms singly bound to carbon atoms not being acetal carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
- C07D317/22—Radicals substituted by singly bound oxygen or sulfur atoms etherified
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Epoxy Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP04291091.9 | 2004-04-27 | ||
| EP04291091A EP1591434B1 (en) | 2004-04-27 | 2004-04-27 | New 1-methoxy-2-phenyl ethenes useful for the preparation of 5-carboxaldehyde-2-3-dihydrobenzoxepines |
| PCT/EP2005/003550 WO2005102977A1 (en) | 2004-04-27 | 2005-04-05 | New 1-methoxy-2-phenyl ethenes for the preparation of 5-carboxaldehyde-2-3-dihydrobenzoxepines |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007534709A JP2007534709A (ja) | 2007-11-29 |
| JP2007534709A5 JP2007534709A5 (https=) | 2008-05-22 |
| JP4772780B2 true JP4772780B2 (ja) | 2011-09-14 |
Family
ID=34931056
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007509908A Expired - Fee Related JP4772780B2 (ja) | 2004-04-27 | 2005-04-05 | ５−カルボキシアルデヒド−２−３−ジヒドロベンゾオキセピン調製のための新規な１−メトキシ−２−フェニルエテン |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US7442814B2 (https=) |
| EP (2) | EP1591434B1 (https=) |
| JP (1) | JP4772780B2 (https=) |
| AR (1) | AR048770A1 (https=) |
| AT (2) | ATE360606T1 (https=) |
| AU (1) | AU2005235671B2 (https=) |
| CA (1) | CA2564733A1 (https=) |
| CY (1) | CY1106649T1 (https=) |
| DE (2) | DE602004006085T2 (https=) |
| DK (1) | DK1591434T3 (https=) |
| ES (2) | ES2285377T3 (https=) |
| PL (1) | PL1591434T3 (https=) |
| PT (1) | PT1591434E (https=) |
| SI (1) | SI1591434T1 (https=) |
| WO (1) | WO2005102977A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5907418B2 (ja) * | 2011-03-25 | 2016-04-26 | 日油株式会社 | 水酸基含有アセタール化合物の製造方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003517449A (ja) * | 1998-12-29 | 2003-05-27 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | ベンゾピランおよびベンツオキセピン、それらを含む医薬組成物および製造方法 |
-
2004
- 2004-04-27 DE DE602004006085T patent/DE602004006085T2/de not_active Expired - Lifetime
- 2004-04-27 AT AT04291091T patent/ATE360606T1/de active
- 2004-04-27 SI SI200430368T patent/SI1591434T1/sl unknown
- 2004-04-27 PL PL04291091T patent/PL1591434T3/pl unknown
- 2004-04-27 ES ES04291091T patent/ES2285377T3/es not_active Expired - Lifetime
- 2004-04-27 PT PT04291091T patent/PT1591434E/pt unknown
- 2004-04-27 EP EP04291091A patent/EP1591434B1/en not_active Expired - Lifetime
- 2004-04-27 DK DK04291091T patent/DK1591434T3/da active
-
2005
- 2005-04-05 WO PCT/EP2005/003550 patent/WO2005102977A1/en not_active Ceased
- 2005-04-05 ES ES05730358T patent/ES2360408T3/es not_active Expired - Lifetime
- 2005-04-05 CA CA002564733A patent/CA2564733A1/en not_active Abandoned
- 2005-04-05 US US11/587,488 patent/US7442814B2/en not_active Expired - Fee Related
- 2005-04-05 DE DE602005026641T patent/DE602005026641D1/de not_active Expired - Lifetime
- 2005-04-05 AU AU2005235671A patent/AU2005235671B2/en not_active Ceased
- 2005-04-05 AT AT05730358T patent/ATE500211T1/de not_active IP Right Cessation
- 2005-04-05 EP EP05730358A patent/EP1740523B1/en not_active Expired - Lifetime
- 2005-04-05 JP JP2007509908A patent/JP4772780B2/ja not_active Expired - Fee Related
- 2005-04-27 AR ARP050101654A patent/AR048770A1/es unknown
-
2007
- 2007-06-11 CY CY20071100769T patent/CY1106649T1/el unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003517449A (ja) * | 1998-12-29 | 2003-05-27 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフトング | ベンゾピランおよびベンツオキセピン、それらを含む医薬組成物および製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1591434A1 (en) | 2005-11-02 |
| ES2360408T3 (es) | 2011-06-03 |
| DK1591434T3 (da) | 2007-09-17 |
| WO2005102977A1 (en) | 2005-11-03 |
| DE602004006085T2 (de) | 2007-12-27 |
| AU2005235671A1 (en) | 2005-11-03 |
| US7442814B2 (en) | 2008-10-28 |
| AR048770A1 (es) | 2006-05-24 |
| SI1591434T1 (sl) | 2007-10-31 |
| EP1740523A1 (en) | 2007-01-10 |
| CY1106649T1 (el) | 2012-01-25 |
| US20070219381A1 (en) | 2007-09-20 |
| ATE360606T1 (de) | 2007-05-15 |
| JP2007534709A (ja) | 2007-11-29 |
| ATE500211T1 (de) | 2011-03-15 |
| PT1591434E (pt) | 2007-07-11 |
| EP1740523B1 (en) | 2011-03-02 |
| CA2564733A1 (en) | 2005-11-03 |
| PL1591434T3 (pl) | 2007-09-28 |
| AU2005235671B2 (en) | 2011-03-17 |
| EP1591434B1 (en) | 2007-04-25 |
| DE602004006085D1 (de) | 2007-06-06 |
| ES2285377T3 (es) | 2007-11-16 |
| DE602005026641D1 (de) | 2011-04-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR100695964B1 (ko) | 2-아미노말론산유도체의 제조방법 | |
| US9604914B2 (en) | Process for preparing N-(4-cyclohexyl-3-trifluoromethyl-benzyloxy)-acetimidic acid ethyl ester | |
| JPH01305076A (ja) | タキソールを調製する方法 | |
| JP7553689B2 (ja) | フェニルイソオキサゾリン系化合物の製造方法 | |
| JPH0625039A (ja) | シクロヘキサントリオール誘導体 | |
| JP2014201545A (ja) | ２−ヒドロキシメチル−２，３−ジヒドロ−チエノ［３，４−ｂ］［１，４］ジオキシン−５，７−ジカルボン酸ジアルキルエステルの製造方法 | |
| JP5115477B2 (ja) | 水酸基を有する３−エチルオキセタン化合物及びその製法 | |
| JP4772780B2 (ja) | ５−カルボキシアルデヒド−２−３−ジヒドロベンゾオキセピン調製のための新規な１−メトキシ−２−フェニルエテン | |
| KR101728443B1 (ko) | 2-아미노니코틴산벤질에스테르 유도체의 제조 방법 | |
| WO2017164379A1 (ja) | ２－アルキルカルボニルナフト［２，３－ｂ］フラン－４，９－ジオンの関連物質の製造方法、及びその関連物質 | |
| US10562834B2 (en) | Process for preparing substituted crotonic acids | |
| JP2009132624A (ja) | ２，３−ジシアノナフタレン誘導体 | |
| CN101121708A (zh) | 奥沙碘铵及其类似物的合成新方法 | |
| CN103183591B (zh) | 4′-二烷氧基甲基双环己烷-4-基甲醇及其制造方法 | |
| Kuang et al. | A convenient and efficient asymmetric synthesis of (S)-α-arylthiomethyl-α-hydroxybutyric acid esters | |
| JPWO1999038828A1 (ja) | ブタントリオール誘導体の製造法 | |
| CN116063216B (zh) | 一种钯催化脱羧[3+2]环加成反应 | |
| ES2703518T3 (es) | Proceso mejorado para la preparación de derivados de ácido 2-(7-metilbenzo[d][1,3]dioxol-4-il 6-(sustituido))acético 2-sustituido | |
| JPH09183749A (ja) | ３，３−ジオキシ−４，４，４−トリフルオロ酪酸誘導体 | |
| KR20250110245A (ko) | 스틸벤 및 이의 중간체의 합성 공정 | |
| KR100618232B1 (ko) | 팜시클로버의 제조방법 | |
| JPH0822830B2 (ja) | ２（ｚ）−ペンテニル置換シクロペンタン類およびその新規中間体 | |
| JP2008001662A (ja) | ２−アシルアミノイミダゾール−４−アルデヒド誘導体の新規合成法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20080402 |
|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20080402 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20110119 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20110119 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20110418 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20110525 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20110622 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20140701 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| LAPS | Cancellation because of no payment of annual fees |