RU2008139612A - METHOD FOR PRODUCING A LINEZOLIDE - Google Patents
METHOD FOR PRODUCING A LINEZOLIDE Download PDFInfo
- Publication number
- RU2008139612A RU2008139612A RU2008139612/04A RU2008139612A RU2008139612A RU 2008139612 A RU2008139612 A RU 2008139612A RU 2008139612/04 A RU2008139612/04 A RU 2008139612/04A RU 2008139612 A RU2008139612 A RU 2008139612A RU 2008139612 A RU2008139612 A RU 2008139612A
- Authority
- RU
- Russia
- Prior art keywords
- compound
- amino
- chloro
- propan
- bromophenyl
- Prior art date
Links
- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 title claims abstract 5
- 229960003907 linezolid Drugs 0.000 title claims abstract 5
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 32
- 238000000034 method Methods 0.000 claims abstract 19
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims abstract 9
- 125000004799 bromophenyl group Chemical group 0.000 claims abstract 9
- 125000000068 chlorophenyl group Chemical group 0.000 claims abstract 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 5
- -1 (S) -5 - {[(4-bromobenzylidene) amino] methyl} -3- (3-fluoro-4-morpholin-4-ylphenyl) oxazolidine Chemical compound 0.000 claims abstract 4
- 230000003993 interaction Effects 0.000 claims abstract 4
- QUIRMPBFJNOJKI-SECBINFHSA-N (2s)-1-chloro-3-[(2,4-dichlorophenyl)methylideneamino]propan-2-ol Chemical compound ClC[C@@H](O)CN=CC1=CC=C(Cl)C=C1Cl QUIRMPBFJNOJKI-SECBINFHSA-N 0.000 claims abstract 3
- LFVZLCKHDSVJFP-KUKWCLJQSA-N ClC[C@@H](O)C\N=C\C1=CC=C(Cl)C=C1 Chemical compound ClC[C@@H](O)C\N=C\C1=CC=C(Cl)C=C1 LFVZLCKHDSVJFP-KUKWCLJQSA-N 0.000 claims abstract 3
- QZNSUKJDFNQCRL-KUKWCLJQSA-N ClC[C@@H](O)C\N=C\c1ccc(Br)cc1 Chemical compound ClC[C@@H](O)C\N=C\c1ccc(Br)cc1 QZNSUKJDFNQCRL-KUKWCLJQSA-N 0.000 claims abstract 3
- JBMVQABQXFJXCV-IBGZPJMESA-N C1COCCN1C2=C(C=C(C=C2)N3C[C@@H](OC3)CN=CC4=CC=C(C=C4)Cl)F Chemical compound C1COCCN1C2=C(C=C(C=C2)N3C[C@@H](OC3)CN=CC4=CC=C(C=C4)Cl)F JBMVQABQXFJXCV-IBGZPJMESA-N 0.000 claims abstract 2
- 230000010933 acylation Effects 0.000 claims abstract 2
- 238000005917 acylation reaction Methods 0.000 claims abstract 2
- 230000007062 hydrolysis Effects 0.000 claims abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- OMPURGCNIGTEBA-SFHVURJKSA-N (5s)-5-[[(4-chlorophenyl)methylideneamino]methyl]-3-(3-fluoro-4-morpholin-4-ylphenyl)-1,3-oxazolidin-2-one Chemical compound FC1=CC(N2C(O[C@@H](CN=CC=3C=CC(Cl)=CC=3)C2)=O)=CC=C1N1CCOCC1 OMPURGCNIGTEBA-SFHVURJKSA-N 0.000 claims 1
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 238000010583 slow cooling Methods 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 230000009466 transformation Effects 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 0 *OC(Nc(cc1)cc(F)c1N1CCOCC1)=O Chemical compound *OC(Nc(cc1)cc(F)c1N1CCOCC1)=O 0.000 description 1
- KSNAGWRTXFLBQI-FARCUNLSSA-N C/C=N/CC(CCl)O Chemical compound C/C=N/CC(CCl)O KSNAGWRTXFLBQI-FARCUNLSSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/04—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C251/06—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton
- C07C251/08—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of a saturated carbon skeleton being acyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/08—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1. Способ получения линезолида ! ! который включает: ! a) взаимодействие соединения структуры (1) ! ! где X представляет собой хлорфенил, бромфенил или 2,4-дихлорфенил, ! с соединением структуры (2) ! ! при температуре в диапазоне от температуры окружающей среды до приблизительно 65°C, где R представляет собой бензил или C1-8алкил, с получением соединения структуры (3): ! ! где X представляет собой хлорфенил, бромфенил или 2,4-дихлорфенил; ! б) гидролиз соединения структуры (3) и последующее ацилирование с получением линезолида. ! 2. Способ по п.1, где соединение структуры (1) представляет собой (S)-1-хлор-3-[(4-хлор-E-бензилиден)амино]пропан-2-ол. ! 3. Способ по п.1, где соединение структуры (1) представляет собой (S)-1-хлор-3-[(4-бром-E-бензилиден)амино]пропан-2-ол. ! 4. Способ по п.1, где соединение структуры (1) представляет собой (S)-1-хлор-3-[(2,4-дихлорбензилиден)амино]пропан-2-ол. ! 5. Способ по п.1, где соединение структуры (3) представляет собой (S)-5-{[(4-хлорбензилиден)амино]метил}-3-(3-фтор-4-морфолин-4-илфенил)оксазолидин-2-он. ! 6. Способ по п.1, где соединение структуры (3) представляет собой (S)-5-{[(4-бромбензилиден)амино]метил}-3-(3-фтор-4-морфолин-4-илфенил)оксазолидин-2-он. ! 7. Способ по п.1, где соединение структуры (3) представляет собой (S)-5-{[(2,4-дихлорбензилиден)амино]метил}-3-(3-фтор-4-морфолин-4-илфенил)оксазолидин-2-он. ! 8. Способ по п.1, где R представляет собой бензил. ! 9. Способ получения соединения структуры (3) ! ! где X представляет собой хлорфенил, бромфенил или 2,4-дихлорфенил, ! который включает ! a) взаимодействие соединения структуры (1) ! ! где X представляет собой хлорфенил, бромфенил или 2,4-дихлорфенил, ! с соединением структуры (2) ! ! при температуре в ди 1. The method of obtaining linezolid! ! which includes:! a) the interaction of the compounds of structure (1)! ! where X is chlorophenyl, bromophenyl or 2,4-dichlorophenyl! with compound structure (2)! ! at a temperature ranging from ambient to about 65 ° C, where R is benzyl or C1-8 alkyl, to give a compound of structure (3):! ! where X is chlorophenyl, bromophenyl or 2,4-dichlorophenyl; ! b) hydrolysis of the compound of structure (3) and subsequent acylation to obtain linezolid. ! 2. The method according to claim 1, where the compound of structure (1) is (S) -1-chloro-3 - [(4-chloro-E-benzylidene) amino] propan-2-ol. ! 3. The method according to claim 1, where the compound of structure (1) is (S) -1-chloro-3 - [(4-bromo-E-benzylidene) amino] propan-2-ol. ! 4. The method according to claim 1, where the compound of structure (1) is (S) -1-chloro-3 - [(2,4-dichlorobenzylidene) amino] propan-2-ol. ! 5. The method according to claim 1, where the compound of structure (3) is (S) -5 - {[(4-chlorobenzylidene) amino] methyl} -3- (3-fluoro-4-morpholin-4-ylphenyl) oxazolidine -2-he. ! 6. The method according to claim 1, where the compound of structure (3) is (S) -5 - {[(4-bromobenzylidene) amino] methyl} -3- (3-fluoro-4-morpholin-4-ylphenyl) oxazolidine -2-he. ! 7. The method according to claim 1, where the compound of structure (3) is (S) -5 - {[((2,4-dichlorobenzylidene) amino] methyl} -3- (3-fluoro-4-morpholin-4-ylphenyl ) oxazolidin-2-one. ! 8. The method according to claim 1, where R is benzyl. ! 9. A method of obtaining a compound of structure (3)! ! where X is chlorophenyl, bromophenyl or 2,4-dichlorophenyl! which includes! a) the interaction of the compounds of structure (1)! ! where X is chlorophenyl, bromophenyl or 2,4-dichlorophenyl! with compound structure (2)! ! at temperature in di
Claims (15)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79036006P | 2006-04-07 | 2006-04-07 | |
| US60/790,360 | 2006-04-07 | ||
| US81698306P | 2006-06-28 | 2006-06-28 | |
| US60/816,983 | 2006-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2008139612A true RU2008139612A (en) | 2010-04-20 |
Family
ID=38308763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008139612/04A RU2008139612A (en) | 2006-04-07 | 2007-03-26 | METHOD FOR PRODUCING A LINEZOLIDE |
Country Status (11)
| Country | Link |
|---|---|
| EP (1) | EP2007740A1 (en) |
| JP (1) | JP2007277243A (en) |
| KR (1) | KR20080104178A (en) |
| AR (1) | AR060299A1 (en) |
| AU (1) | AU2007235635A1 (en) |
| BR (1) | BRPI0710312A2 (en) |
| CA (1) | CA2648178A1 (en) |
| MX (1) | MX2008012941A (en) |
| RU (1) | RU2008139612A (en) |
| TW (1) | TW200808782A (en) |
| WO (1) | WO2007116284A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2792687C1 (en) * | 2019-08-20 | 2023-03-23 | Хангжоу Дике Технологиес Ко., Лтд. | Method for synthesis of n-substituted phenyl-5-hydroxymethyl-2-oxazolidinone |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010084514A2 (en) * | 2009-01-02 | 2010-07-29 | Neuland Laboratories Ltd. | A process for the preparation of (5s)-(n)-[[3-[3-fluoro-4-(4-morpholinyl) phenyl]-2-oxo-5-oxazolidinyl] methyl] acetamide |
| CN101774978B (en) | 2009-01-13 | 2011-09-21 | 联化科技股份有限公司 | Preparation method of linezolid and intermediate thereof |
| BR112012027901A2 (en) | 2010-04-30 | 2015-09-08 | Univ Indiana Res & Tech Corp | processes for preparing linezolid |
| WO2012019632A1 (en) | 2010-08-11 | 2012-02-16 | Synthon B.V. | Process for making linezolid |
| EP2690100A1 (en) | 2010-08-11 | 2014-01-29 | Synhton B.V. | Process for making linezolid |
| ES2395304B1 (en) * | 2011-05-20 | 2014-01-16 | Interquim, S.A. | PROCEDURE FOR OBTAINING A THIOPHEN-2-CARBOXAMIDE. |
| CN102827154B (en) * | 2011-06-14 | 2015-04-22 | 上海科胜药物研发有限公司 | New method for synthesizing rivaroxaban intermediate 4-{4-[(5S)-5-(aminomethyl)-2-oxo-1,3-oxazolidine-3-yl]phenyl}morpholine-3-ketone |
| WO2013072923A1 (en) | 2011-09-19 | 2013-05-23 | Cadila Healthcare Limited | Process for the preparation of crystalline linezolid |
| CN103254148B (en) | 2012-02-15 | 2016-04-13 | 浙江海正药业股份有限公司 | The preparation method of linezolid intermediate |
| CZ2012111A3 (en) | 2012-02-16 | 2013-08-28 | Zentiva, K.S. | Process for preparing rivaroxaban based on the use of (S)-epichlorohydrin |
| ES2603252T3 (en) | 2012-11-09 | 2017-02-24 | Synthon Bv | Process to prepare linezolid |
| US9643939B1 (en) | 2016-04-18 | 2017-05-09 | Optimus Drugs Private Limited | Process for the preparation of linezolid |
| USRE47606E1 (en) | 2016-04-21 | 2019-09-17 | Optimus Drugs Private Limited | Process for the preparation of linezolid |
| CN110579556B (en) * | 2018-06-08 | 2024-11-05 | 四川科伦药物研究院有限公司 | Testing methods for linezolid products |
| CN115236236A (en) * | 2022-07-26 | 2022-10-25 | 上海市食品药品检验研究院 | Linezolid and separation and analysis method of enantiomers in preparation thereof |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5688792A (en) * | 1994-08-16 | 1997-11-18 | Pharmacia & Upjohn Company | Substituted oxazine and thiazine oxazolidinone antimicrobials |
| DE69738457T2 (en) * | 1996-04-11 | 2008-12-24 | Pharmacia & Upjohn Co. Llc, Kalamazoo | Process for the preparation of oxazolidinones |
| KR100619639B1 (en) * | 1997-11-07 | 2006-09-06 | 파마시아 앤드 업존 캄파니 엘엘씨 | Process to Produce Oxazolidinones |
-
2007
- 2007-03-26 RU RU2008139612/04A patent/RU2008139612A/en not_active Application Discontinuation
- 2007-03-26 MX MX2008012941A patent/MX2008012941A/en unknown
- 2007-03-26 CA CA002648178A patent/CA2648178A1/en not_active Abandoned
- 2007-03-26 BR BRPI0710312-3A patent/BRPI0710312A2/en not_active IP Right Cessation
- 2007-03-26 WO PCT/IB2007/000882 patent/WO2007116284A1/en not_active Ceased
- 2007-03-26 EP EP07734203A patent/EP2007740A1/en not_active Withdrawn
- 2007-03-26 AU AU2007235635A patent/AU2007235635A1/en not_active Abandoned
- 2007-03-26 KR KR1020087024348A patent/KR20080104178A/en not_active Ceased
- 2007-04-04 AR ARP070101433A patent/AR060299A1/en not_active Application Discontinuation
- 2007-04-04 TW TW096112188A patent/TW200808782A/en unknown
- 2007-04-06 JP JP2007099953A patent/JP2007277243A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2792687C1 (en) * | 2019-08-20 | 2023-03-23 | Хангжоу Дике Технологиес Ко., Лтд. | Method for synthesis of n-substituted phenyl-5-hydroxymethyl-2-oxazolidinone |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2007740A1 (en) | 2008-12-31 |
| JP2007277243A (en) | 2007-10-25 |
| WO2007116284A1 (en) | 2007-10-18 |
| TW200808782A (en) | 2008-02-16 |
| AU2007235635A1 (en) | 2007-10-18 |
| BRPI0710312A2 (en) | 2011-08-09 |
| MX2008012941A (en) | 2008-10-15 |
| AR060299A1 (en) | 2008-06-04 |
| KR20080104178A (en) | 2008-12-01 |
| CA2648178A1 (en) | 2007-10-18 |
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