CA2883323A1 - Aldehyde derivative of substituted oxazolidinones - Google Patents
Aldehyde derivative of substituted oxazolidinones Download PDFInfo
- Publication number
- CA2883323A1 CA2883323A1 CA2883323A CA2883323A CA2883323A1 CA 2883323 A1 CA2883323 A1 CA 2883323A1 CA 2883323 A CA2883323 A CA 2883323A CA 2883323 A CA2883323 A CA 2883323A CA 2883323 A1 CA2883323 A1 CA 2883323A1
- Authority
- CA
- Canada
- Prior art keywords
- formula
- compound
- rivaroxaban
- compound formula
- test
- 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
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 170
- 238000000034 method Methods 0.000 claims abstract description 20
- 238000002360 preparation method Methods 0.000 claims abstract description 20
- 238000011282 treatment Methods 0.000 claims abstract description 12
- 230000008569 process Effects 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
- 230000009424 thromboembolic effect Effects 0.000 claims abstract description 7
- 239000002904 solvent Substances 0.000 claims description 30
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- 239000000203 mixture Substances 0.000 claims description 27
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 20
- -1 sulfonyloxy, imidazole Chemical group 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 10
- 235000019253 formic acid Nutrition 0.000 claims description 10
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- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 5
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- 150000003141 primary amines Chemical group 0.000 claims description 5
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 claims description 4
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 claims description 4
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- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
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- 125000003545 alkoxy group Chemical group 0.000 claims description 4
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
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- HOGDNTQCSIKEEV-UHFFFAOYSA-N n'-hydroxybutanediamide Chemical group NC(=O)CCC(=O)NO HOGDNTQCSIKEEV-UHFFFAOYSA-N 0.000 claims description 4
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 4
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims 2
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- 238000004821 distillation Methods 0.000 claims 1
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- BWEPHOKPIKTSCJ-ZDUSSCGKSA-N n-[[(5s)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]formamide Chemical compound O=C1O[C@@H](CNC=O)CN1C1=CC=C(N2C(COCC2)=O)C=C1 BWEPHOKPIKTSCJ-ZDUSSCGKSA-N 0.000 claims 1
- 235000006408 oxalic acid Nutrition 0.000 claims 1
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- 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 abstract description 95
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Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
- A61K31/5375—1,4-Oxazines, e.g. morpholine
- A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- C07D413/10—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 carbon chain containing aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN3359/MUM/2012 | 2012-12-26 | ||
| PCT/IN2013/000801 WO2014102822A2 (en) | 2012-12-26 | 2013-12-24 | Aldehyde derivative of substitute oxazolidinones |
| IN3359MU2012 IN2012MU03359A (cg-RX-API-DMAC7.html) | 2012-12-26 | 2013-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2883323A1 true CA2883323A1 (en) | 2014-07-03 |
Family
ID=54242230
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2883323A Abandoned CA2883323A1 (en) | 2012-12-26 | 2013-12-24 | Aldehyde derivative of substituted oxazolidinones |
Country Status (15)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20161588T1 (hr) | 2012-12-26 | 2017-01-13 | Wanbury Limited | Intermedijer rivaroksabana i njegova priprava |
| US20160251342A1 (en) * | 2012-12-26 | 2016-09-01 | Wanbury Ltd. | Aldehyde derivative of substituted oxazolidinones |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19962924A1 (de) | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
| DE10129725A1 (de) * | 2001-06-20 | 2003-01-02 | Bayer Ag | Kombinationstherapie substituierter Oxazolidinone |
| 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 |
| DE102004002044A1 (de) | 2004-01-15 | 2005-08-04 | Bayer Healthcare Ag | Herstellverfahren |
| GT200600196A (es) | 2005-05-23 | 2007-01-15 | Compuestos n-formil de hidroxilamina | |
| DE102005045518A1 (de) | 2005-09-23 | 2007-03-29 | Bayer Healthcare Ag | 2-Aminoethoxyessigsäure-Derivate und ihre Verwendung |
| CA2624310C (en) | 2005-10-04 | 2014-01-07 | Bayer Healthcare Ag | Polymorphic form of 5-chloro-n-({5s)-2-oxo-3-[4-(3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidin-5-yl}-methyl)-2-thiophenecarboxamide |
| DE102006007146A1 (de) * | 2006-02-16 | 2007-08-23 | Bayer Healthcare Ag | Aminoacyl-Prodrugs |
| DE102006039589A1 (de) * | 2006-08-24 | 2008-03-06 | Bayer Healthcare Ag | Aminoacyl-Prodrugs II |
| JP5389028B2 (ja) | 2007-08-14 | 2014-01-15 | コンサート ファーマシューティカルズ インコーポレイテッド | 置換オキサゾリジノン誘導体 |
| US7816355B1 (en) | 2009-04-28 | 2010-10-19 | Apotex Pharmachem Inc | Processes for the preparation of rivaroxaban and intermediates thereof |
| EP2459555B1 (en) | 2009-07-31 | 2021-11-03 | KRKA, D.D., Novo Mesto | Processes for crystallization of rivaroxaban |
| US20120283434A1 (en) | 2010-01-04 | 2012-11-08 | Enantia, S.L. | Process for the preparation of rivaroxaban and intermediates thereof |
| EP2354128A1 (en) | 2010-02-10 | 2011-08-10 | Sandoz Ag | Method for the preparation of rivaroxaban |
| EA201370107A1 (ru) * | 2010-11-11 | 2013-11-29 | Редкс Фарма Лимитед | Производные лекарственных средств |
| WO2012140061A1 (en) | 2011-04-11 | 2012-10-18 | Sandoz Ag | Method for the preparation of substituted oxazolidinones |
| GEP20156397B (en) | 2011-05-06 | 2015-11-10 | Egis Gyógyszergyár Nyilvánosan Működő Részvénytársaság | Process for the preparation of a rivaroxaban and intermediates formed in said process |
| ES2395304B1 (es) | 2011-05-20 | 2014-01-16 | Interquim, S.A. | Procedimiento de obtención de una tiofen-2-carboxamida. |
| HRP20161588T1 (hr) | 2012-12-26 | 2017-01-13 | Wanbury Limited | Intermedijer rivaroksabana i njegova priprava |
-
2013
- 2013-12-24 IN IN3359MU2012 patent/IN2012MU03359A/en unknown
- 2013-12-24 CA CA2883323A patent/CA2883323A1/en not_active Abandoned
- 2013-12-24 AU AU2013368847A patent/AU2013368847B2/en not_active Expired - Fee Related
- 2013-12-24 US US14/436,018 patent/US9359341B2/en not_active Expired - Fee Related
- 2013-12-24 EP EP13869179.5A patent/EP2897619A4/en not_active Withdrawn
- 2013-12-24 RU RU2015112195A patent/RU2015112195A/ru not_active Application Discontinuation
- 2013-12-24 BR BR112015011033A patent/BR112015011033A2/pt not_active IP Right Cessation
- 2013-12-24 KR KR1020157015903A patent/KR20150100661A/ko not_active Ceased
- 2013-12-24 MX MX2015003319A patent/MX2015003319A/es unknown
- 2013-12-24 CN CN201380068642.9A patent/CN105431429A/zh active Pending
- 2013-12-24 JP JP2015550211A patent/JP2016504348A/ja active Pending
- 2013-12-24 HK HK16105076.8A patent/HK1217101A1/zh unknown
- 2013-12-24 WO PCT/IN2013/000801 patent/WO2014102822A2/en not_active Ceased
-
2015
- 2015-05-25 ZA ZA2015/03700A patent/ZA201503700B/en unknown
- 2015-07-22 PH PH12015501625A patent/PH12015501625A1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| MX2015003319A (es) | 2015-08-14 |
| CN105431429A (zh) | 2016-03-23 |
| IN2012MU03359A (cg-RX-API-DMAC7.html) | 2015-06-26 |
| US9359341B2 (en) | 2016-06-07 |
| EP2897619A2 (en) | 2015-07-29 |
| KR20150100661A (ko) | 2015-09-02 |
| EP2897619A4 (en) | 2016-08-17 |
| RU2015112195A (ru) | 2017-01-31 |
| HK1217101A1 (zh) | 2016-12-23 |
| ZA201503700B (en) | 2016-10-26 |
| AU2013368847B2 (en) | 2017-03-16 |
| BR112015011033A2 (pt) | 2017-07-11 |
| WO2014102822A2 (en) | 2014-07-03 |
| US20150259333A1 (en) | 2015-09-17 |
| WO2014102822A3 (en) | 2015-10-29 |
| PH12015501625A1 (en) | 2015-09-28 |
| AU2013368847A1 (en) | 2015-05-28 |
| JP2016504348A (ja) | 2016-02-12 |
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| Date | Code | Title | Description |
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| EEER | Examination request |
Effective date: 20160613 |
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| FZDE | Dead |
Effective date: 20181106 |