JP2006520351A - シアノイソベンゾフランの製造方法 - Google Patents
シアノイソベンゾフランの製造方法 Download PDFInfo
- Publication number
- JP2006520351A JP2006520351A JP2006504646A JP2006504646A JP2006520351A JP 2006520351 A JP2006520351 A JP 2006520351A JP 2006504646 A JP2006504646 A JP 2006504646A JP 2006504646 A JP2006504646 A JP 2006504646A JP 2006520351 A JP2006520351 A JP 2006520351A
- Authority
- JP
- Japan
- Prior art keywords
- fluorophenyl
- dihydro
- isobenzofurancarbonitrile
- hydroxymethyl
- bis
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 12
- DNEVVXBMQZYGEI-UHFFFAOYSA-N 2-benzofuran-1-carbonitrile Chemical compound C1=CC=CC2=C(C#N)OC=C21 DNEVVXBMQZYGEI-UHFFFAOYSA-N 0.000 title description 2
- YXCRMKYHFFMNPT-UHFFFAOYSA-N 1-(4-fluorophenyl)-1,3-dihydro-2-benzofuran-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C1C2=CC=C(C#N)C=C2CO1 YXCRMKYHFFMNPT-UHFFFAOYSA-N 0.000 claims abstract description 42
- XEEGWTLAFIZLSF-UHFFFAOYSA-N 1-oxo-3h-2-benzofuran-5-carbonitrile Chemical compound N#CC1=CC=C2C(=O)OCC2=C1 XEEGWTLAFIZLSF-UHFFFAOYSA-N 0.000 claims abstract description 29
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims abstract description 27
- WSEQXVZVJXJVFP-HXUWFJFHSA-N (R)-citalopram Chemical compound C1([C@@]2(C3=CC=C(C=C3CO2)C#N)CCCN(C)C)=CC=C(F)C=C1 WSEQXVZVJXJVFP-HXUWFJFHSA-N 0.000 claims abstract description 25
- 229960001653 citalopram Drugs 0.000 claims abstract description 25
- WDWABVHVASZWHB-UHFFFAOYSA-N 1,1-bis(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile Chemical compound C1=CC(F)=CC=C1C1(C=2C=CC(F)=CC=2)C2=CC=C(C#N)C=C2CO1 WDWABVHVASZWHB-UHFFFAOYSA-N 0.000 claims abstract description 21
- -1 4-fluorophenylmagnesium halide Chemical class 0.000 claims abstract description 20
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- GDOCLIOVHKLEOU-UHFFFAOYSA-N 4-(4-fluorobenzoyl)-3-(hydroxymethyl)benzonitrile Chemical compound OCC1=CC(C#N)=CC=C1C(=O)C1=CC=C(F)C=C1 GDOCLIOVHKLEOU-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 11
- JOWBVIAXILQDHG-UHFFFAOYSA-N 4-[(4-fluorophenyl)-hydroxymethyl]-3-(hydroxymethyl)benzonitrile Chemical compound OCC1=CC(C#N)=CC=C1C(O)C1=CC=C(F)C=C1 JOWBVIAXILQDHG-UHFFFAOYSA-N 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000002576 ketones Chemical class 0.000 claims abstract description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 81
- 239000000203 mixture Substances 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- BNUIKEORRSAIAY-UHFFFAOYSA-N 4-[bis(4-fluorophenyl)-hydroxymethyl]-3-(hydroxymethyl)benzonitrile Chemical compound OCC1=CC(C#N)=CC=C1C(O)(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 BNUIKEORRSAIAY-UHFFFAOYSA-N 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 16
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 12
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 10
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 7
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
- 239000012458 free base Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000012312 sodium hydride Substances 0.000 claims description 5
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 5
- ZLXJXAMSNFFEFG-UHFFFAOYSA-N 1,3-dihydro-2-benzofuran-5-carbonitrile Chemical compound N#CC1=CC=C2COCC2=C1 ZLXJXAMSNFFEFG-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 230000002051 biphasic effect Effects 0.000 claims 4
- MLGVWRLCURBYNQ-UHFFFAOYSA-N 2-benzofuran-5-carbonitrile Chemical compound C1=C(C#N)C=CC2=COC=C21 MLGVWRLCURBYNQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001207 fluorophenyl group Chemical group 0.000 claims 2
- TZAITSBCLSGKMM-UHFFFAOYSA-N 1-(4-fluorophenyl)-3h-2-benzofuran-1-carbonitrile Chemical compound C1=CC(F)=CC=C1C1(C#N)C2=CC=CC=C2CO1 TZAITSBCLSGKMM-UHFFFAOYSA-N 0.000 claims 1
- 229940072018 zofran Drugs 0.000 claims 1
- ZQGAXHXHVKVERC-UHFFFAOYSA-N 1-benzofuran-2-carbonitrile Chemical compound C1=CC=C2OC(C#N)=CC2=C1 ZQGAXHXHVKVERC-UHFFFAOYSA-N 0.000 abstract description 4
- 239000000243 solution Substances 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- 239000012074 organic phase Substances 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000008346 aqueous phase Substances 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 17
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 15
- 239000012071 phase Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 238000004128 high performance liquid chromatography Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 8
- BRKADVNLTRCLOW-UHFFFAOYSA-M magnesium;fluorobenzene;bromide Chemical compound [Mg+2].[Br-].FC1=CC=[C-]C=C1 BRKADVNLTRCLOW-UHFFFAOYSA-M 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000012790 confirmation Methods 0.000 description 6
- 238000005191 phase separation Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 150000002825 nitriles Chemical class 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- WIHMBLDNRMIGDW-UHFFFAOYSA-N 1-[3-(dimethylamino)propyl]-1-(4-fluorophenyl)-3h-2-benzofuran-5-carbonitrile;hydron;bromide Chemical compound [Br-].O1CC2=CC(C#N)=CC=C2C1(CCC[NH+](C)C)C1=CC=C(F)C=C1 WIHMBLDNRMIGDW-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 235000019270 ammonium chloride Nutrition 0.000 description 4
- 229960000584 citalopram hydrobromide Drugs 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 150000002009 diols Chemical class 0.000 description 4
- 230000008034 disappearance Effects 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 229910052749 magnesium Inorganic materials 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- AITNMTXHTIIIBB-UHFFFAOYSA-N 1-bromo-4-fluorobenzene Chemical compound FC1=CC=C(Br)C=C1 AITNMTXHTIIIBB-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- IUSPXLCLQIZFHL-UHFFFAOYSA-N 5-bromo-3h-2-benzofuran-1-one Chemical compound BrC1=CC=C2C(=O)OCC2=C1 IUSPXLCLQIZFHL-UHFFFAOYSA-N 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 3
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 2
- NYYRRBOMNHUCLB-UHFFFAOYSA-N 3-chloro-n,n-dimethylpropan-1-amine Chemical compound CN(C)CCCCl NYYRRBOMNHUCLB-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000003747 Grignard reaction Methods 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 230000014509 gene expression Effects 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002680 magnesium Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- NHKJPPKXDNZFBJ-UHFFFAOYSA-N phenyllithium Chemical compound [Li]C1=CC=CC=C1 NHKJPPKXDNZFBJ-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- NWRXEGKWQXAEHC-UHFFFAOYSA-N 2-(hydroxymethyl)benzonitrile Chemical compound OCC1=CC=CC=C1C#N NWRXEGKWQXAEHC-UHFFFAOYSA-N 0.000 description 1
- OFQCQIGMURIECL-UHFFFAOYSA-N 2-[2-(diethylamino)ethyl]-2',6'-dimethylspiro[isoquinoline-4,4'-oxane]-1,3-dione;phosphoric acid Chemical compound OP(O)(O)=O.O=C1N(CCN(CC)CC)C(=O)C2=CC=CC=C2C21CC(C)OC(C)C2 OFQCQIGMURIECL-UHFFFAOYSA-N 0.000 description 1
- PUIVIZQHTBRFTR-UHFFFAOYSA-N 3-oxo-1h-2-benzofuran-1-carbonitrile Chemical compound C1=CC=C2C(=O)OC(C#N)C2=C1 PUIVIZQHTBRFTR-UHFFFAOYSA-N 0.000 description 1
- CBTIEHGGPCWUAD-UHFFFAOYSA-N C1C2=C(C=CC(=C2)C#N)C(O1)C3=CC=CC=C3 Chemical compound C1C2=C(C=CC(=C2)C#N)C(O1)C3=CC=CC=C3 CBTIEHGGPCWUAD-UHFFFAOYSA-N 0.000 description 1
- 208000020401 Depressive disease Diseases 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- GCJYYUGXODRJJT-UHFFFAOYSA-N [4-bromo-2-(hydroxymethyl)phenyl]-(4-fluorophenyl)methanol Chemical compound OCC1=CC(Br)=CC=C1C(O)C1=CC=C(F)C=C1 GCJYYUGXODRJJT-UHFFFAOYSA-N 0.000 description 1
- DSXGDABDEZITPU-UHFFFAOYSA-N [4-bromo-2-(hydroxymethyl)phenyl]-(4-fluorophenyl)methanone Chemical compound OCC1=CC(Br)=CC=C1C(=O)C1=CC=C(F)C=C1 DSXGDABDEZITPU-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 238000004042 decolorization Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- NGPAITITALWALP-UHFFFAOYSA-M magnesium;n,n-dimethylpropan-1-amine;chloride Chemical compound [Mg+2].[Cl-].CN(C)CC[CH2-] NGPAITITALWALP-UHFFFAOYSA-M 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000479A ITMI20030479A1 (it) | 2003-03-13 | 2003-03-13 | Procedimento per la preparazione di un ciano-isobenzofurano. |
| PCT/EP2004/002522 WO2004080988A1 (en) | 2003-03-13 | 2004-03-09 | Process for the preparation of a cyano-isobenzofuran |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006520351A true JP2006520351A (ja) | 2006-09-07 |
| JP2006520351A5 JP2006520351A5 (https=) | 2007-04-26 |
Family
ID=32983208
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006504646A Pending JP2006520351A (ja) | 2003-03-13 | 2004-03-09 | シアノイソベンゾフランの製造方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7411077B2 (https=) |
| EP (1) | EP1601662A1 (https=) |
| JP (1) | JP2006520351A (https=) |
| KR (1) | KR20050108376A (https=) |
| CN (1) | CN1761658A (https=) |
| AU (1) | AU2004220410A1 (https=) |
| BR (1) | BRPI0408732A (https=) |
| CA (1) | CA2514458A1 (https=) |
| HR (1) | HRP20050893A2 (https=) |
| IT (1) | ITMI20030479A1 (https=) |
| MX (1) | MXPA05008411A (https=) |
| WO (1) | WO2004080988A1 (https=) |
| ZA (1) | ZA200505592B (https=) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2005283422C1 (en) | 2004-09-17 | 2017-02-02 | Eisai R & D Management Co., Ltd. | Medicinal composition |
| WO2008059514A2 (en) * | 2006-07-31 | 2008-05-22 | Cadila Healthcare Limited | Process for preparing escitalopram |
| JP6687625B2 (ja) | 2014-12-30 | 2020-04-22 | ダウ アグロサイエンシィズ エルエルシー | 殺真菌活性を有するピコリンアミド化合物 |
| CN109640657B (zh) | 2016-07-07 | 2020-10-30 | 美国陶氏益农公司 | 制备4-烷氧基-3-(酰基或脂族饱和烃基)氧基吡啶甲酰胺的方法 |
| CN108929245A (zh) * | 2017-05-25 | 2018-12-04 | 万全万特制药江苏有限公司 | 艾司西酞普兰工艺杂质的制备方法 |
| CN108947869A (zh) * | 2017-05-25 | 2018-12-07 | 万全万特制药江苏有限公司 | 一种艾司西酞普兰工艺杂质的制备方法 |
| CN120097946A (zh) * | 2025-02-28 | 2025-06-06 | 浙江工业大学 | 一种应用脱水膜强化5-氰二醇盐酸盐醚化制西酞普兰溴酸盐的方法 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52105162A (en) * | 1976-01-14 | 1977-09-03 | Kefalas As | Phthleic derivatives and preparation thereof |
| JP2002509526A (ja) * | 1997-07-08 | 2002-03-26 | ハー・ルンドベック・アクティーゼルスカブ | シタロプラムの製造方法 |
| JP2002121161A (ja) * | 1999-11-01 | 2002-04-23 | Sumika Fine Chemicals Co Ltd | ５−フタランカルボニトリル化合物の製造方法、その中間体およびその製造方法 |
| JP2002121189A (ja) * | 2000-02-17 | 2002-04-23 | Sumika Fine Chemicals Co Ltd | シタロプラムの製造方法、およびその中間体とその製造方法 |
| JP2002530295A (ja) * | 1997-11-11 | 2002-09-17 | ハー・ルンドベック・アクチエゼルスカベット | シタロプラムの製造方法 |
| JP2002530296A (ja) * | 1997-11-10 | 2002-09-17 | ハー・ルンドベック・アクチエゼルスカベット | シタロプラムの製造方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6310222B1 (en) * | 1999-11-01 | 2001-10-30 | Sumika Fine Chemicals Co., Ltd. | Production method of 5-phthalancarbonitrile compound, intermediate therefor and production method of the intermediate |
| US6433196B1 (en) | 2000-02-17 | 2002-08-13 | Sumika Fine Chemicals Co., Ltd. | Production method of citalopram, intermediate therefor and production method of the intermediate |
-
2003
- 2003-03-13 IT IT000479A patent/ITMI20030479A1/it unknown
-
2004
- 2004-03-09 AU AU2004220410A patent/AU2004220410A1/en not_active Abandoned
- 2004-03-09 EP EP04718658A patent/EP1601662A1/en not_active Withdrawn
- 2004-03-09 WO PCT/EP2004/002522 patent/WO2004080988A1/en not_active Ceased
- 2004-03-09 JP JP2006504646A patent/JP2006520351A/ja active Pending
- 2004-03-09 US US10/549,062 patent/US7411077B2/en not_active Expired - Fee Related
- 2004-03-09 KR KR1020057016274A patent/KR20050108376A/ko not_active Withdrawn
- 2004-03-09 MX MXPA05008411A patent/MXPA05008411A/es unknown
- 2004-03-09 ZA ZA200505592A patent/ZA200505592B/en unknown
- 2004-03-09 CA CA002514458A patent/CA2514458A1/en not_active Abandoned
- 2004-03-09 BR BRPI0408732-1A patent/BRPI0408732A/pt not_active IP Right Cessation
- 2004-03-09 HR HR20050893A patent/HRP20050893A2/hr not_active Application Discontinuation
- 2004-03-09 CN CNA2004800068530A patent/CN1761658A/zh active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52105162A (en) * | 1976-01-14 | 1977-09-03 | Kefalas As | Phthleic derivatives and preparation thereof |
| JP2002509526A (ja) * | 1997-07-08 | 2002-03-26 | ハー・ルンドベック・アクティーゼルスカブ | シタロプラムの製造方法 |
| JP2002530296A (ja) * | 1997-11-10 | 2002-09-17 | ハー・ルンドベック・アクチエゼルスカベット | シタロプラムの製造方法 |
| JP2002530295A (ja) * | 1997-11-11 | 2002-09-17 | ハー・ルンドベック・アクチエゼルスカベット | シタロプラムの製造方法 |
| JP2002121161A (ja) * | 1999-11-01 | 2002-04-23 | Sumika Fine Chemicals Co Ltd | ５−フタランカルボニトリル化合物の製造方法、その中間体およびその製造方法 |
| JP2002121189A (ja) * | 2000-02-17 | 2002-04-23 | Sumika Fine Chemicals Co Ltd | シタロプラムの製造方法、およびその中間体とその製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2514458A1 (en) | 2004-09-23 |
| ITMI20030479A1 (it) | 2004-09-14 |
| CN1761658A (zh) | 2006-04-19 |
| US7411077B2 (en) | 2008-08-12 |
| ZA200505592B (en) | 2006-09-27 |
| KR20050108376A (ko) | 2005-11-16 |
| AU2004220410A1 (en) | 2004-09-23 |
| HRP20050893A2 (en) | 2005-12-31 |
| MXPA05008411A (es) | 2005-10-05 |
| EP1601662A1 (en) | 2005-12-07 |
| US20060183925A1 (en) | 2006-08-17 |
| WO2004080988A1 (en) | 2004-09-23 |
| BRPI0408732A (pt) | 2006-03-07 |
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