WO2005026135A1 - Verfahren zur herstellung von 4-(4-aminophenyl)-3-morpholinon - Google Patents
Verfahren zur herstellung von 4-(4-aminophenyl)-3-morpholinon Download PDFInfo
- Publication number
- WO2005026135A1 WO2005026135A1 PCT/EP2004/010054 EP2004010054W WO2005026135A1 WO 2005026135 A1 WO2005026135 A1 WO 2005026135A1 EP 2004010054 W EP2004010054 W EP 2004010054W WO 2005026135 A1 WO2005026135 A1 WO 2005026135A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- morpholinone
- aminophenyl
- preparation
- nitrophenyl
- phenyl
- Prior art date
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- MHCRLDZZHOVFEE-UHFFFAOYSA-N 4-(4-aminophenyl)morpholin-3-one Chemical compound C1=CC(N)=CC=C1N1C(=O)COCC1 MHCRLDZZHOVFEE-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- OWMGEFWSGOTGAU-UHFFFAOYSA-N 4-(4-nitrophenyl)morpholin-3-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1N1C(=O)COCC1 OWMGEFWSGOTGAU-UHFFFAOYSA-N 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 6
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 13
- SIWXCJHUZAEIAE-UHFFFAOYSA-N 4-phenylmorpholin-3-one Chemical compound O=C1COCCN1C1=CC=CC=C1 SIWXCJHUZAEIAE-UHFFFAOYSA-N 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 5
- -1 3- oxo-4-morpholinyl Chemical group 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 238000006396 nitration reaction Methods 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 3
- 239000000706 filtrate Substances 0.000 claims description 3
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 claims description 3
- 238000010626 work up procedure Methods 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 claims description 2
- 230000008025 crystallization Effects 0.000 claims description 2
- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 claims description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- MWGATWIBSKHFMR-UHFFFAOYSA-N 2-anilinoethanol Chemical compound OCCNC1=CC=CC=C1 MWGATWIBSKHFMR-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- DUILGEYLVHGSEE-ZETCQYMHSA-N 2-[[(2s)-oxiran-2-yl]methyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C[C@H]1CO1 DUILGEYLVHGSEE-ZETCQYMHSA-N 0.000 description 2
- BMPDCQVRKDNUAP-UHFFFAOYSA-N 5-chlorothiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)S1 BMPDCQVRKDNUAP-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- KGFYHTZWPPHNLQ-AWEZNQCLSA-N rivaroxaban Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC(=O)N(C=2C=CC(=CC=2)N2C(COCC2)=O)C1 KGFYHTZWPPHNLQ-AWEZNQCLSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- PGOHTUIFYSHAQG-LJSDBVFPSA-N (2S)-6-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-4-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-5-amino-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-amino-2-[[(2S)-1-[(2S,3R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-amino-4-methylsulfanylbutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-methylpentanoyl]amino]acetyl]amino]-3-hydroxypropanoyl]amino]-4-methylpentanoyl]amino]-3-sulfanylpropanoyl]amino]-4-methylsulfanylbutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-hydroxybutanoyl]pyrrolidine-2-carbonyl]amino]-5-oxopentanoyl]amino]-3-hydroxypropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-4-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-5-carbamimidamidopentanoyl]amino]-5-oxopentanoyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxypropanoyl]amino]-3-carboxypropanoyl]amino]-3-hydroxypropanoyl]amino]-5-oxopentanoyl]amino]-5-oxopentanoyl]amino]-3-phenylpropanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-methylbutanoyl]amino]-4-methylpentanoyl]amino]-4-oxobutanoyl]amino]-5-carbamimidamidopentanoyl]amino]-3-(1H-indol-3-yl)propanoyl]amino]-4-carboxybutanoyl]amino]-5-oxopentanoyl]amino]hexanoic acid Chemical compound CSCC[C@H](N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](Cc1cnc[nH]1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCCN)C(O)=O PGOHTUIFYSHAQG-LJSDBVFPSA-N 0.000 description 1
- WFQDTOYDVUWQMS-UHFFFAOYSA-N 1-fluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1 WFQDTOYDVUWQMS-UHFFFAOYSA-N 0.000 description 1
- FHQRDEDZJIFJAL-UHFFFAOYSA-N 4-phenylmorpholine Chemical compound C1COCCN1C1=CC=CC=C1 FHQRDEDZJIFJAL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- VEUUMBGHMNQHGO-UHFFFAOYSA-N ethyl chloroacetate Chemical compound CCOC(=O)CCl VEUUMBGHMNQHGO-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000009424 thromboembolic effect Effects 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
- C07D265/32—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
Definitions
- the invention relates to a process for the preparation of 4- (4-An inophenyl) -3-mor- pholinone by reacting 4- (4-nitrophenyl) -3-morpholinone with hydrogen in the presence of a hydrogenation catalyst, characterized in that the reaction in a Alcoholic alcohol takes place.
- 4- (4-Aminophenyl) -3-morpholinone is a Central Precursor in the Synthesis of 5-Chloro-N- ( ⁇ (5S) -2-oxo-3- [4- (3-oxo-4-morpholinyl) - phenyl] -l, 3-oxazolidin-5-yl ⁇ -methyl) -2-thiophenecarboxamide, an inhibitor of the blood coagulation factor Xa, which can be used for the prophylaxis and / or treatment of various thromboembolic disorders (see WO-A 01/47919 the disclosure of which is hereby incorporated by reference).
- WO-A 02/48099 4- (4-aminophenyl) -3-morpholinone is also described as a precursor for the synthesis of active ingredients, but there is no indication whatsoever of the preparation of this compound.
- WO-A 01/47919 also describes a preparation method for 4- (4-aminophenyl) -3-morpholinone (I).
- Morpholine-3-one (V) is first deprotonated with sodium hydride and then reacted with 4-fluoronitrobenzene (VI) to give 4- (4-nitrophenyl) -3-morpholinone (VH).
- Catalytic hydrogenation of (VH) with hydrogen over palladium on charcoal in tetrahydrofuran as solvent gives 4- (4-aminophenyl) -3-morpholinone (I):
- the product-containing filtrate is further reacted directly without 4- (4-aminophenyl) -3-morpholinone (I) being isolated in bulk.
- VE 4- (4-Nitrophenyl) -3-morpholinone
- V1H 4-phenyl-3-morpholinone
- VITJ 4-phenyl-3-morpholinone
- the reaction mixture is added at -10 to 0 ° C with 0.9 to 1.2 equivalents of 65% nitric acid.
- the unwanted ortho and meta isomers are formed in addition to the desired para-isomer.
- 5 to 15 ° C water and 25% aqueous ammonia solution are added to the reaction mixture until a pH of 7 to 7.5 is reached.
- 2-anilinoethanol is presented in aqueous alcoholic, preferably ethanolic solution.
- aqueous alcoholic preferably ethanolic solution.
- 2.5 to 3.5 equivalents of chloroacetyl chloride and 4 to 8, preferably 5 to 7 equivalents of base are metered in at the same time.
- the base used are aqueous alkali metal or alkaline earth metal hydroxide solutions, preferably sodium hydroxide or potassium hydroxide solutions, in particular aqueous sodium hydroxide solution.
- the addition takes place at an internal temperature of the reaction solution of 30 to 50 ° C, preferably from 35 to 45 ° C.
- the rate of addition is adjusted so that the pH of the reaction solution is between 10 and 13.5, preferably between 12 and 12.5.
- the product (VEI) crystallizes out and can be obtained by filtration and washing with cold water in good yield and high purity.
- Another object of the present invention is prepared according to the invention 4- (4-aminophenyl) -3-morpholinone.
- Another object of the present invention is the use of inventively prepared 4- (4-aminophenyl) -3-morpholinone for the preparation of 5-chloro-N - ( ⁇ (5S) -2-oxo-3- [4- (3-oxo 4-morpholinyl) -phenyl] -l, 3-oxazolidin-5-yl ⁇ methyl) -2-thiophenecarboxamide (IV).
- the suspension is mixed with 2000 g of acetone and heated to 40 ° C.
- the product goes into solution so that the phases can be separated.
- 1500 g of acetone are added to the organic phase.
- distilled off clay / water mixture wherein the product precipitates.
- the suspension is cooled to 10 ° C, stirred for 30 minutes and the product is isolated.
- the moist product is washed with 320 g of cold acetone and dried in vacuo at 50 ° C.
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK04764990.0T DK1664004T3 (en) | 2003-09-15 | 2004-09-09 | METHOD FOR PREPARING 4- (4-AMINOPHENYL) -3-MORPHOLINON |
| SI200432262T SI1664004T1 (sl) | 2003-09-15 | 2004-09-09 | Postopek izdelave 4-(4-aminofenil)-3-morfolinona |
| PL04764990T PL1664004T3 (pl) | 2003-09-15 | 2004-09-09 | Sposób wytwarzania 4-(4-aminofenylo)-3-morfolinonu |
| CA2538906A CA2538906C (en) | 2003-09-15 | 2004-09-09 | Process for preparing 4-(4-aminophenyl)-3-morpholinone |
| KR1020067005136A KR101148264B1 (ko) | 2003-09-15 | 2004-09-09 | 4-(4-아미노페닐)-3-모폴리논 제조 방법 |
| AU2004272255A AU2004272255B2 (en) | 2003-09-15 | 2004-09-09 | Method for the production of 4-(4-aminophenyl)-3-morpholinon |
| HK07104349.3A HK1098134B (en) | 2003-09-15 | 2004-09-09 | Method for the production of 4-(4-aminophenyl)-3-morpholinon |
| BRPI0414382-5A BRPI0414382B1 (pt) | 2003-09-15 | 2004-09-09 | Processo para preparação de 4-(4-aminofenil)-3-morfolinona |
| EP04764990.0A EP1664004B1 (de) | 2003-09-15 | 2004-09-09 | Verfahren zur herstellung von 4-(4-aminophenyl)-3-morpholinon |
| IN411DEN2012 IN2012DN00411A (forum.php) | 2003-09-15 | 2004-09-09 | |
| JP2006525762A JP4852419B2 (ja) | 2003-09-15 | 2004-09-09 | ４−（４−アミノフェニル）−３−モルホリノンの製造方法 |
| MXPA06002883A MXPA06002883A (es) | 2003-09-15 | 2004-09-09 | Procedimiento para preparar la 4-(4-aminofenil)-3-morfolinona. |
| US10/571,364 US7598378B2 (en) | 2003-09-15 | 2004-09-09 | Method for the production of 4-(4-aminophenyl)-3-morpholinone |
| ES04764990.0T ES2545072T3 (es) | 2003-09-15 | 2004-09-09 | Procedimiento para la preparación de 4-(4-aminofenil)-3-morfolinona |
| IL174194A IL174194A (en) | 2003-09-15 | 2006-03-09 | Method for the production of 4-(4-aminophenyl)-3-morpholinon |
| EGPCTNA2006000246A EG26605A (en) | 2003-09-15 | 2006-03-13 | Process for the preparation of 4- (4-aminophenyl) -3-morpholine |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10342570A DE10342570A1 (de) | 2003-09-15 | 2003-09-15 | Verfahren zur Herstellung von 4-(4-Aminophenyl)-3-morpholinon |
| DE10342570.5 | 2003-09-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2005026135A1 true WO2005026135A1 (de) | 2005-03-24 |
Family
ID=34305779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/EP2004/010054 WO2005026135A1 (de) | 2003-09-15 | 2004-09-09 | Verfahren zur herstellung von 4-(4-aminophenyl)-3-morpholinon |
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| EP (1) | EP1664004B1 (forum.php) |
| JP (1) | JP4852419B2 (forum.php) |
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| DE (1) | DE10342570A1 (forum.php) |
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| PL (1) | PL1664004T3 (forum.php) |
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| KR100898361B1 (ko) | 2008-07-03 | 2009-05-20 | 주식회사 레고켐 바이오사이언스 | Ｐ4 위치에 사이클릭 아미독심 또는 사이클릭 아미드라존기를 가지는 ＦＸａ 저해제, 이의 유도체, 제조방법 및이를 함유하는 의약 조성물 |
| WO2011080341A1 (en) | 2010-01-04 | 2011-07-07 | Enantia, S.L. | Process for the preparation of rivaroxaban and intermediates thereof |
| WO2011131316A1 (de) * | 2010-04-23 | 2011-10-27 | Archimica Gmbh | Verfahren zur herstellung von 4-(4-aminophenyl)-morpholin-3-on |
| WO2012140061A1 (en) | 2011-04-11 | 2012-10-18 | Sandoz Ag | Method for the preparation of substituted oxazolidinones |
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| CN103232446A (zh) * | 2013-05-17 | 2013-08-07 | 天津药物研究院 | 一种噁唑烷酮衍生物晶型ⅱ及其制备方法和用途 |
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| CN102320988B (zh) * | 2011-06-03 | 2014-04-09 | 中国科学院上海有机化学研究所 | 4-(4-氨基苯基)-3-吗啉酮中间体酰胺、合成方法和用途 |
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- 2004-09-09 BR BRPI0414382-5A patent/BRPI0414382B1/pt not_active IP Right Cessation
- 2004-09-09 AU AU2004272255A patent/AU2004272255B2/en not_active Expired
- 2004-09-09 PT PT47649900T patent/PT1664004E/pt unknown
- 2004-09-09 EP EP04764990.0A patent/EP1664004B1/de not_active Expired - Lifetime
- 2004-09-09 CA CA2538906A patent/CA2538906C/en not_active Expired - Lifetime
- 2004-09-09 HU HUE04764990A patent/HUE025273T2/en unknown
- 2004-09-09 US US10/571,364 patent/US7598378B2/en active Active
- 2004-09-09 KR KR1020067005136A patent/KR101148264B1/ko not_active Expired - Lifetime
- 2004-09-09 MX MXPA06002883A patent/MXPA06002883A/es active IP Right Grant
- 2004-09-09 PL PL04764990T patent/PL1664004T3/pl unknown
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- 2004-09-09 IN IN411DEN2012 patent/IN2012DN00411A/en unknown
- 2004-09-09 DK DK04764990.0T patent/DK1664004T3/en active
- 2004-09-09 WO PCT/EP2004/010054 patent/WO2005026135A1/de active Application Filing
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Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100898361B1 (ko) | 2008-07-03 | 2009-05-20 | 주식회사 레고켐 바이오사이언스 | Ｐ4 위치에 사이클릭 아미독심 또는 사이클릭 아미드라존기를 가지는 ＦＸａ 저해제, 이의 유도체, 제조방법 및이를 함유하는 의약 조성물 |
| WO2011080341A1 (en) | 2010-01-04 | 2011-07-07 | Enantia, S.L. | Process for the preparation of rivaroxaban and intermediates thereof |
| WO2011131316A1 (de) * | 2010-04-23 | 2011-10-27 | Archimica Gmbh | Verfahren zur herstellung von 4-(4-aminophenyl)-morpholin-3-on |
| WO2012140061A1 (en) | 2011-04-11 | 2012-10-18 | Sandoz Ag | Method for the preparation of substituted oxazolidinones |
| WO2012153155A1 (en) | 2011-05-06 | 2012-11-15 | Egis Gyógyszergyár Nyilvãnosan Müködö Részvény-Társaság | Process for the preparation of a rivaroxaban and intermediates formed in said process |
| MD4557B1 (ro) * | 2011-05-06 | 2018-03-31 | Egis Gyogysszegyar Nyilvanosan Mukodo Reszvenytarsasag | Procedeu de obţinere a rivaroxabanului şi un compus intermediar utilizat în acest procedeu |
| CN103288814A (zh) * | 2012-02-24 | 2013-09-11 | 上海医药工业研究院 | 一种利伐沙班中间体的制备方法 |
| CN103288814B (zh) * | 2012-02-24 | 2016-07-06 | 国药集团国瑞药业有限公司 | 一种利伐沙班中间体的制备方法 |
| WO2014175563A1 (en) * | 2013-04-25 | 2014-10-30 | Chong Kun Dang Pharmaceutical Corp. | Novel method of preparing 4-(4-aminophenyl)-3-morpholinone |
| CN103232446B (zh) * | 2013-05-17 | 2015-09-23 | 天津药物研究院 | 一种噁唑烷酮衍生物晶型ⅱ及其制备方法和用途 |
| CN103232446A (zh) * | 2013-05-17 | 2013-08-07 | 天津药物研究院 | 一种噁唑烷酮衍生物晶型ⅱ及其制备方法和用途 |
| US9751843B2 (en) | 2013-11-08 | 2017-09-05 | Bayer Pharma Aktiengesellschaft | Substituted uracils and use thereof |
| CN103709116A (zh) * | 2013-12-10 | 2014-04-09 | 四川大学 | 一种4-(4-烷氧羰氨基)苯基-3-吗啉酮的制备方法 |
| CN103709116B (zh) * | 2013-12-10 | 2015-09-23 | 四川大学 | 一种4-(4-烷氧羰氨基)苯基-3-吗啉酮的制备方法 |
| WO2019138362A1 (en) | 2018-01-12 | 2019-07-18 | Richter Gedeon Nyrt. | Process for the preparation of 4-(4-aminophenyl)morpholin-3-one |
Also Published As
| Publication number | Publication date |
|---|---|
| IN2012DN00411A (forum.php) | 2015-08-21 |
| DE10342570A1 (de) | 2005-04-14 |
| CA2538906A1 (en) | 2005-03-24 |
| KR101148264B1 (ko) | 2012-05-21 |
| PL1664004T3 (pl) | 2015-11-30 |
| IL174194A0 (en) | 2006-08-01 |
| KR20060070561A (ko) | 2006-06-23 |
| PT1664004E (pt) | 2015-09-21 |
| DK1664004T3 (en) | 2015-09-07 |
| EP1664004B1 (de) | 2015-06-24 |
| EP1664004A1 (de) | 2006-06-07 |
| US20070066611A1 (en) | 2007-03-22 |
| HK1098134A1 (zh) | 2007-07-13 |
| EG26605A (en) | 2014-03-23 |
| IL174194A (en) | 2010-11-30 |
| AU2004272255A1 (en) | 2005-03-24 |
| CY1116644T1 (el) | 2017-03-15 |
| ES2545072T3 (es) | 2015-09-08 |
| SI1664004T1 (sl) | 2015-10-30 |
| ZA200602093B (en) | 2007-05-30 |
| CA2538906C (en) | 2013-04-23 |
| US7598378B2 (en) | 2009-10-06 |
| JP2007505821A (ja) | 2007-03-15 |
| MXPA06002883A (es) | 2006-06-05 |
| HUE025273T2 (en) | 2016-02-29 |
| AU2004272255B2 (en) | 2011-01-06 |
| CN1852902A (zh) | 2006-10-25 |
| CN100430384C (zh) | 2008-11-05 |
| BRPI0414382A (pt) | 2006-11-21 |
| BRPI0414382B1 (pt) | 2014-01-28 |
| JP4852419B2 (ja) | 2012-01-11 |
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