ES2684125T3 - Estereoisómero de acetamida - Google Patents
Estereoisómero de acetamida Download PDFInfo
- Publication number
- ES2684125T3 ES2684125T3 ES08829102.6T ES08829102T ES2684125T3 ES 2684125 T3 ES2684125 T3 ES 2684125T3 ES 08829102 T ES08829102 T ES 08829102T ES 2684125 T3 ES2684125 T3 ES 2684125T3
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- Prior art keywords
- pharmaceutical composition
- compound
- composition according
- formula
- pharmaceutically acceptable
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- 150000003869 acetamides Chemical class 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 61
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000006239 protecting group Chemical group 0.000 claims description 7
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 230000002441 reversible effect Effects 0.000 claims description 5
- 206010006482 Bronchospasm Diseases 0.000 claims description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical group NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims description 4
- 230000007885 bronchoconstriction Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003431 steroids Chemical class 0.000 claims description 4
- 239000004475 Arginine Substances 0.000 claims description 3
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 3
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 3
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- 229960001888 ipratropium Drugs 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
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- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- VOVIALXJUBGFJZ-KWVAZRHASA-N Budesonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@@H]2[C@@H]1[C@@H]1C[C@H]3OC(CCC)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O VOVIALXJUBGFJZ-KWVAZRHASA-N 0.000 claims description 2
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- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 claims description 2
- VPNYRYCIDCJBOM-UHFFFAOYSA-M Glycopyrronium bromide Chemical compound [Br-].C1[N+](C)(C)CCC1OC(=O)C(O)(C=1C=CC=CC=1)C1CCCC1 VPNYRYCIDCJBOM-UHFFFAOYSA-M 0.000 claims description 2
- 102000003816 Interleukin-13 Human genes 0.000 claims description 2
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- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- 229960004308 acetylcysteine Drugs 0.000 claims description 2
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- NBMKJKDGKREAPL-DVTGEIKXSA-N beclomethasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CO)(O)[C@@]1(C)C[C@@H]2O NBMKJKDGKREAPL-DVTGEIKXSA-N 0.000 claims description 2
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- ZNEWHQLOPFWXOF-UHFFFAOYSA-N coenzyme M Chemical compound OS(=O)(=O)CCS ZNEWHQLOPFWXOF-UHFFFAOYSA-N 0.000 claims description 2
- 229940109248 cromoglycate Drugs 0.000 claims description 2
- IMZMKUWMOSJXDT-UHFFFAOYSA-N cromoglycic acid Chemical compound O1C(C(O)=O)=CC(=O)C2=C1C=CC=C2OCC(O)COC1=CC=CC2=C1C(=O)C=C(C(O)=O)O2 IMZMKUWMOSJXDT-UHFFFAOYSA-N 0.000 claims description 2
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- 239000003112 inhibitor Substances 0.000 claims description 2
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- 229960001664 mometasone Drugs 0.000 claims description 2
- QLIIKPVHVRXHRI-CXSFZGCWSA-N mometasone Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(Cl)[C@@H]1[C@@H]1C[C@@H](C)[C@@](C(=O)CCl)(O)[C@@]1(C)C[C@@H]2O QLIIKPVHVRXHRI-CXSFZGCWSA-N 0.000 claims description 2
- 230000000770 proinflammatory effect Effects 0.000 claims description 2
- 229960005294 triamcinolone Drugs 0.000 claims description 2
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 claims description 2
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- 208000027771 Obstructive airways disease Diseases 0.000 claims 2
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- 230000000510 mucolytic effect Effects 0.000 claims 2
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- MIXMJCQRHVAJIO-TZHJZOAOSA-N qk4dys664x Chemical compound O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O.C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@@H]1[C@@H]2[C@@H]2C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]2(C)C[C@@H]1O MIXMJCQRHVAJIO-TZHJZOAOSA-N 0.000 claims 1
- LERNTVKEWCAPOY-DZZGSBJMSA-N tiotropium Chemical compound O([C@H]1C[C@@H]2[N+]([C@H](C1)[C@@H]1[C@H]2O1)(C)C)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 LERNTVKEWCAPOY-DZZGSBJMSA-N 0.000 claims 1
- 229940110309 tiotropium Drugs 0.000 claims 1
- 239000000243 solution Substances 0.000 description 42
- 239000000203 mixture Substances 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 22
- 238000009472 formulation Methods 0.000 description 20
- 239000000443 aerosol Substances 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 235000019439 ethyl acetate Nutrition 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 108060003345 Adrenergic Receptor Proteins 0.000 description 10
- 102000017910 Adrenergic receptor Human genes 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- 230000000694 effects Effects 0.000 description 10
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000003380 propellant Substances 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical compound C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 description 8
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- 239000004094 surface-active agent Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 4
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- FYJDOJRVHFOYFZ-CWTRNNRKSA-N n-[2-hydroxy-5-[(1s)-1-hydroxy-2-[[(2r)-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenyl]acetamide Chemical compound C([C@@H](C)NC[C@@H](O)C=1C=C(NC(C)=O)C(O)=CC=1)C1=CC=C(O)C=C1 FYJDOJRVHFOYFZ-CWTRNNRKSA-N 0.000 description 4
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
- C07C233/42—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
- C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
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- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/4015—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil having oxo groups directly attached to the heterocyclic ring, e.g. piracetam, ethosuximide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/0075—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy for inhalation via a dry powder inhaler [DPI], e.g. comprising micronized drug mixed with lactose carrier particles
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/16—Preparation of optical isomers
- C07C231/18—Preparation of optical isomers by stereospecific synthesis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Otolaryngology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96643807P | 2007-08-28 | 2007-08-28 | |
| US966438P | 2007-08-28 | ||
| PCT/US2008/074653 WO2009032764A1 (en) | 2007-08-28 | 2008-08-28 | Acetamide stereoisomer |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2684125T3 true ES2684125T3 (es) | 2018-10-01 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES08829102.6T Active ES2684125T3 (es) | 2007-08-28 | 2008-08-28 | Estereoisómero de acetamida |
Country Status (12)
| Country | Link |
|---|---|
| US (4) | US8501994B2 (enExample) |
| EP (1) | EP2195285B1 (enExample) |
| JP (1) | JP5468543B2 (enExample) |
| KR (1) | KR101398775B1 (enExample) |
| AR (1) | AR072943A1 (enExample) |
| AU (1) | AU2008296458B2 (enExample) |
| CA (1) | CA2696943C (enExample) |
| ES (1) | ES2684125T3 (enExample) |
| MX (1) | MX2010001978A (enExample) |
| NZ (1) | NZ583462A (enExample) |
| TW (1) | TWI505826B (enExample) |
| WO (1) | WO2009032764A1 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200510277A (en) * | 2003-05-27 | 2005-03-16 | Theravance Inc | Crystalline form of β2-adrenergic receptor agonist |
| US8501994B2 (en) | 2007-08-28 | 2013-08-06 | Sunovion Pharmaceuticals Inc. | Acetamide stereoisomer |
| EP2578570A1 (en) | 2011-10-07 | 2013-04-10 | Almirall, S.A. | Novel process for preparing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1(r)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one via novel intermediates of synthesis. |
| EP2641900A1 (en) | 2012-03-20 | 2013-09-25 | Almirall, S.A. | Novel polymorphic Crystal forms of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-(R)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one, heminapadisylate as agonist of the ß2 adrenergic receptor. |
| JP2022521600A (ja) * | 2019-02-22 | 2022-04-11 | シラ セラピューティック インコーポレイティッド | 吸入可能な治療剤 |
| CN111944855B (zh) * | 2020-09-03 | 2022-08-30 | 扬州中宝药业股份有限公司 | 一种合成(r)-1-(4-(苄氧基)-3-硝基苯基)-2-溴乙醇的方法 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| GB1415256A (en) | 1972-02-05 | 1975-11-26 | Yamanouchi Pharma Co Ltd | Alpha-aminomethylbenzyl alcohol derivatives |
| US3994974A (en) * | 1972-02-05 | 1976-11-30 | Yamanouchi Pharmaceutical Co., Ltd. | α-Aminomethylbenzyl alcohol derivatives |
| DE2366625C2 (enExample) | 1972-02-05 | 1988-06-09 | Yamanouchi Pharmaceutical Co., Ltd., Tokio/Tokyo, Jp | |
| JPS4880523A (enExample) * | 1972-02-05 | 1973-10-29 | ||
| JPS599542B2 (ja) * | 1980-06-11 | 1984-03-03 | 山之内製薬株式会社 | 新規な３−アシルアミノ−４−ヒドロキシ−α−（アラルキルアミノメチル）ベンジルアルコ−ルの製法 |
| ES2005492A6 (es) | 1987-12-23 | 1989-03-01 | Lasa Lab | Procedimiento de obtencion de n-(2-hidroxi-5-(1-hidroxi-2((2- (4-metoxifenil)-1metiletil)amino)etil)fenil)foramida (i). |
| ES2031407A6 (es) | 1988-10-05 | 1992-12-01 | Lasa Lab | Mejoras introducidas en el objeto de la patente principal n{ 8703715 por: procedimiento de obtencion de n-(2-hidroxi-5-(1-hidroxi-2-((2-(4-metoxifenil)-1-metiletil)amino)etil)fenil)formamida". |
| CN1083831C (zh) | 1996-01-10 | 2002-05-01 | 旭化成株式会社 | 新的三环化合物及含有它们的药物组合物 |
| DK0938467T3 (da) | 1996-11-11 | 2002-10-07 | Sepracor Inc | Fremgangsmåde til fremstilling af optisk rene isomerer af formoterol |
| US6040344A (en) * | 1996-11-11 | 2000-03-21 | Sepracor Inc. | Formoterol process |
| US6303145B2 (en) * | 1999-05-10 | 2001-10-16 | Sepracor Inc. | (S,R) formoterol methods and compositions |
| US6472563B1 (en) * | 2001-11-09 | 2002-10-29 | Sepracor Inc. | Formoterol tartrate process and polymorph |
| US7718822B2 (en) * | 2007-08-28 | 2010-05-18 | Sepracor Inc. | Carbamate Stereoisomer |
| US8501994B2 (en) * | 2007-08-28 | 2013-08-06 | Sunovion Pharmaceuticals Inc. | Acetamide stereoisomer |
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- 2008-08-28 NZ NZ583462A patent/NZ583462A/en not_active IP Right Cessation
- 2008-08-28 ES ES08829102.6T patent/ES2684125T3/es active Active
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- 2008-08-28 JP JP2010523136A patent/JP5468543B2/ja not_active Expired - Fee Related
- 2008-08-28 KR KR1020107006647A patent/KR101398775B1/ko not_active Expired - Fee Related
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- 2008-08-28 MX MX2010001978A patent/MX2010001978A/es active IP Right Grant
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2013
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2014
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Also Published As
| Publication number | Publication date |
|---|---|
| CA2696943C (en) | 2015-05-26 |
| US9040588B2 (en) | 2015-05-26 |
| AR072943A1 (es) | 2010-10-06 |
| CA2696943A1 (en) | 2009-03-12 |
| US20140135300A1 (en) | 2014-05-15 |
| AU2008296458A1 (en) | 2009-03-12 |
| US8501994B2 (en) | 2013-08-06 |
| US9499476B2 (en) | 2016-11-22 |
| WO2009032764A1 (en) | 2009-03-12 |
| TWI505826B (zh) | 2015-11-01 |
| EP2195285A1 (en) | 2010-06-16 |
| KR101398775B1 (ko) | 2014-05-27 |
| US20130296607A1 (en) | 2013-11-07 |
| KR20100047333A (ko) | 2010-05-07 |
| TW200913984A (en) | 2009-04-01 |
| NZ583462A (en) | 2012-03-30 |
| JP5468543B2 (ja) | 2014-04-09 |
| JP2010538010A (ja) | 2010-12-09 |
| EP2195285B1 (en) | 2018-08-01 |
| US20150225334A1 (en) | 2015-08-13 |
| MX2010001978A (es) | 2010-05-27 |
| US8664441B2 (en) | 2014-03-04 |
| AU2008296458B2 (en) | 2014-01-16 |
| US20090060922A1 (en) | 2009-03-05 |
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