AU2013250801A1 - Process for the preparation of rivaroxaban and intermediates thereof - Google Patents
Process for the preparation of rivaroxaban and intermediates thereof Download PDFInfo
- Publication number
- AU2013250801A1 AU2013250801A1 AU2013250801A AU2013250801A AU2013250801A1 AU 2013250801 A1 AU2013250801 A1 AU 2013250801A1 AU 2013250801 A AU2013250801 A AU 2013250801A AU 2013250801 A AU2013250801 A AU 2013250801A AU 2013250801 A1 AU2013250801 A1 AU 2013250801A1
- Authority
- AU
- Australia
- Prior art keywords
- formula
- compound
- rivaroxaban
- preparation
- iii
- 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.)
- Abandoned
Links
- 238000000034 method Methods 0.000 title claims abstract description 60
- 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 title claims abstract description 36
- 229960001148 rivaroxaban Drugs 0.000 title claims abstract description 35
- 238000002360 preparation method Methods 0.000 title claims abstract description 32
- 239000000543 intermediate Substances 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 90
- 239000000203 mixture Substances 0.000 claims description 27
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- XSGMBZPBLJKZLG-RXMQYKEDSA-N 5-chloro-n-[(2s)-3-chloro-2-hydroxypropyl]thiophene-2-carboxamide Chemical compound ClC[C@@H](O)CNC(=O)C1=CC=C(Cl)S1 XSGMBZPBLJKZLG-RXMQYKEDSA-N 0.000 claims description 5
- BMPDCQVRKDNUAP-UHFFFAOYSA-N 5-chlorothiophene-2-carbonyl chloride Chemical group ClC(=O)C1=CC=C(Cl)S1 BMPDCQVRKDNUAP-UHFFFAOYSA-N 0.000 claims description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- YBNFDPQDRAJWPK-UHFFFAOYSA-N 5-chlorothiophene-2-carbonyl bromide Chemical compound ClC1=CC=C(C(Br)=O)S1 YBNFDPQDRAJWPK-UHFFFAOYSA-N 0.000 claims 1
- OSIVUYFVTDQPMF-UHFFFAOYSA-N 5-chlorothiophene-2-carbonyl iodide Chemical compound ClC1=CC=C(C(I)=O)S1 OSIVUYFVTDQPMF-UHFFFAOYSA-N 0.000 claims 1
- -1 chloro-N-((2R)-2-hydroxy-3- { [4-(3 -oxo-4-morpholinyl)-phenyl] amino } propyl)-2 thiophenecarboxamide Chemical compound 0.000 description 13
- 239000011541 reaction mixture Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000002002 slurry Substances 0.000 description 6
- LLRCNCXTSFGOGG-YFKPBYRVSA-N 5-chloro-n-[[(2s)-oxiran-2-yl]methyl]thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NC[C@@H]1OC1 LLRCNCXTSFGOGG-YFKPBYRVSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 238000010908 decantation Methods 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- KPIKCRCDQKZWBQ-RXMQYKEDSA-N n-[(2s)-3-bromo-2-hydroxypropyl]-5-chlorothiophene-2-carboxamide Chemical compound BrC[C@@H](O)CNC(=O)C1=CC=C(Cl)S1 KPIKCRCDQKZWBQ-RXMQYKEDSA-N 0.000 description 2
- 239000012056 semi-solid material Substances 0.000 description 2
- BRLQWZUYTZBJKN-GSVOUGTGSA-N (+)-Epichlorohydrin Chemical compound ClC[C@@H]1CO1 BRLQWZUYTZBJKN-GSVOUGTGSA-N 0.000 description 1
- ZCPJBHYNOFIAPJ-AENDTGMFSA-N (2s)-1-amino-3-chloropropan-2-ol;hydrochloride Chemical compound Cl.NC[C@H](O)CCl ZCPJBHYNOFIAPJ-AENDTGMFSA-N 0.000 description 1
- ZCPJBHYNOFIAPJ-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl)azanium;chloride Chemical compound Cl.NCC(O)CCl ZCPJBHYNOFIAPJ-UHFFFAOYSA-N 0.000 description 1
- USWMGRHEMVYLCF-UHFFFAOYSA-N 1-aminopropane-1,2-diol hydrochloride Chemical compound Cl.NC(C(C)O)O USWMGRHEMVYLCF-UHFFFAOYSA-N 0.000 description 1
- MHCRLDZZHOVFEE-UHFFFAOYSA-N 4-(4-aminophenyl)morpholin-3-one Chemical compound C1=CC(N)=CC=C1N1C(=O)COCC1 MHCRLDZZHOVFEE-UHFFFAOYSA-N 0.000 description 1
- LLRCNCXTSFGOGG-UHFFFAOYSA-N 5-chloro-n-(oxiran-2-ylmethyl)thiophene-2-carboxamide Chemical compound S1C(Cl)=CC=C1C(=O)NCC1OC1 LLRCNCXTSFGOGG-UHFFFAOYSA-N 0.000 description 1
- KPLVWXBCSNCNJA-YFKPBYRVSA-N 5-chloro-n-[(2s)-2,3-dihydroxypropyl]thiophene-2-carboxamide Chemical compound OC[C@@H](O)CNC(=O)C1=CC=C(Cl)S1 KPLVWXBCSNCNJA-YFKPBYRVSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 159000000021 acetate salts Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000004675 formic acid derivatives Chemical class 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- JNZQZWXLEQBGDK-UHFFFAOYSA-N n-(3-amino-2-hydroxypropyl)-5-chlorothiophene-2-carboxamide Chemical class NCC(O)CNC(=O)C1=CC=C(Cl)S1 JNZQZWXLEQBGDK-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- DENPQNAWGQXKCU-UHFFFAOYSA-N thiophene-2-carboxamide Chemical compound NC(=O)C1=CC=CS1 DENPQNAWGQXKCU-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1174/DEL/2012 | 2012-04-16 | ||
| IN1174DE2012 | 2012-04-16 | ||
| PCT/IB2013/053025 WO2013156936A1 (en) | 2012-04-16 | 2013-04-16 | Process for the preparation of rivaroxaban and intermediates thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2013250801A1 true AU2013250801A1 (en) | 2014-11-06 |
Family
ID=48539327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2013250801A Abandoned AU2013250801A1 (en) | 2012-04-16 | 2013-04-16 | Process for the preparation of rivaroxaban and intermediates thereof |
Country Status (6)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103819468A (zh) * | 2013-12-05 | 2014-05-28 | 浙江天宇药业股份有限公司 | 一种利伐沙班及其中间体的合成方法 |
| WO2015104605A1 (en) | 2014-01-08 | 2015-07-16 | Wockhardt Limited | A process for preparing rivaroxaban or a pharmaceutically acceptable salt thereof |
| CN104478820B (zh) * | 2014-12-22 | 2016-08-31 | 杭州瀚康生物医药科技有限公司 | 一种利伐沙班中间体的制备方法 |
| CN104910141B (zh) * | 2015-05-12 | 2018-11-02 | 浙江天顺生物科技有限公司 | 一种利伐沙班中间体5-氯-n-(2-环氧乙烷基甲基)-2-噻吩甲酰胺的制备方法 |
| CN104788444B (zh) * | 2015-05-12 | 2018-11-06 | 浙江天顺生物科技有限公司 | 利伐沙班的制备方法 |
| CN104817550B (zh) * | 2015-05-26 | 2017-06-16 | 山东铂源药业有限公司 | 一种利伐沙班的制备方法 |
| CN108707080B (zh) * | 2018-06-20 | 2022-01-25 | 上海圣赢生物科技有限公司 | 一种利奈唑胺及其中间体的环保合成方法 |
| CN109400577B (zh) * | 2019-01-07 | 2021-01-19 | 石药集团中奇制药技术（石家庄）有限公司 | 利伐沙班有关化合物及其制备方法和用途 |
| CN112110910B (zh) * | 2019-06-19 | 2024-03-19 | 上海特化医药科技有限公司 | 制备利伐沙班中间体的方法及由其制备利伐沙班的方法 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SK286569B6 (sk) | 1997-11-07 | 2009-01-07 | Pharmacia & Upjohn Company | Spôsob výroby oxazolidinónov |
| DE19962924A1 (de) | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
| DE10300111A1 (de) | 2003-01-07 | 2004-07-15 | Bayer Healthcare Ag | Verfahren zur Herstellung von 5-Chlor-N-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidin-5-yl}-methyl)-2-thiophencarboxamid |
| DE10322469A1 (de) | 2003-05-19 | 2004-12-16 | Bayer Healthcare Ag | Heterocyclische Verbindungen |
| DE102006051625A1 (de) | 2006-11-02 | 2008-05-08 | Bayer Materialscience Ag | Kombinationstherapie substituierter Oxazolidinone |
| DE102007028320A1 (de) * | 2007-06-20 | 2008-12-24 | Bayer Healthcare Ag | Substituierte Oxazolidinone und ihre Verwendung |
| DE102007032347A1 (de) | 2007-07-11 | 2009-01-15 | Bayer Healthcare Ag | Aminoacyl-Prodrugs |
| DE102007032345A1 (de) * | 2007-07-11 | 2009-01-15 | Bayer Healthcare Ag | Aminoacyl-Prodrugs |
| EP2354128A1 (en) | 2010-02-10 | 2011-08-10 | Sandoz Ag | Method for the preparation of rivaroxaban |
| CN102584738B (zh) | 2011-01-07 | 2015-04-29 | 浙江九洲药业股份有限公司 | 一种合成利伐沙班中间体的工艺 |
| WO2013046211A1 (en) * | 2011-09-27 | 2013-04-04 | Symed Labs Limited | Processes for the preparation of 5-chloro-n-({(5s)-2-oxo-3-[4-(3-oxo-4-morpholinyl) phenyl]-1,3-oxazolidin-5-yl}methyl)-2-thiophene-carboxamide and intermediates thereof |
-
2013
- 2013-04-16 AU AU2013250801A patent/AU2013250801A1/en not_active Abandoned
- 2013-04-16 EP EP13726292.9A patent/EP2838897A1/en not_active Withdrawn
- 2013-04-16 WO PCT/IB2013/053025 patent/WO2013156936A1/en active Application Filing
- 2013-04-16 US US14/394,547 patent/US20150299160A1/en not_active Abandoned
- 2013-04-16 SG SG11201406623PA patent/SG11201406623PA/en unknown
- 2013-04-16 IN IN9450DEN2014 patent/IN2014DN09450A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2838897A1 (en) | 2015-02-25 |
| IN2014DN09450A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2015-07-17 |
| SG11201406623PA (en) | 2014-11-27 |
| US20150299160A1 (en) | 2015-10-22 |
| WO2013156936A1 (en) | 2013-10-24 |
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