AU2008293444B2 - Carbamate stereoisomer - Google Patents
Carbamate stereoisomer Download PDFInfo
- Publication number
- AU2008293444B2 AU2008293444B2 AU2008293444A AU2008293444A AU2008293444B2 AU 2008293444 B2 AU2008293444 B2 AU 2008293444B2 AU 2008293444 A AU2008293444 A AU 2008293444A AU 2008293444 A AU2008293444 A AU 2008293444A AU 2008293444 B2 AU2008293444 B2 AU 2008293444B2
- Authority
- AU
- Australia
- Prior art keywords
- compound
- pharmaceutical composition
- protecting group
- hydroxy
- mixture
- 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.)
- Ceased
Links
- 150000004657 carbamic acid derivatives Chemical class 0.000 title description 14
- 150000001875 compounds Chemical class 0.000 claims abstract description 84
- 239000000203 mixture Substances 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- -1 funisolide Chemical compound 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000006239 protecting group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims description 5
- 125000006242 amine protecting group Chemical group 0.000 claims description 5
- 125000001743 benzylic group Chemical group 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 206010006482 Bronchospasm Diseases 0.000 claims description 4
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims description 4
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims description 4
- 230000007885 bronchoconstriction Effects 0.000 claims description 4
- 150000003431 steroids Chemical class 0.000 claims description 4
- 239000004475 Arginine Substances 0.000 claims description 3
- 208000027771 Obstructive airways disease Diseases 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
- OEXHQOGQTVQTAT-JRNQLAHRSA-N ipratropium Chemical group O([C@H]1C[C@H]2CC[C@@H](C1)[N@@+]2(C)C(C)C)C(=O)C(CO)C1=CC=CC=C1 OEXHQOGQTVQTAT-JRNQLAHRSA-N 0.000 claims description 3
- 229960001888 ipratropium Drugs 0.000 claims description 3
- 239000003149 muscarinic antagonist Substances 0.000 claims description 3
- 230000002441 reversible effect Effects 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
- 102000016622 Dipeptidyl Peptidase 4 Human genes 0.000 claims description 2
- 101000930822 Giardia intestinalis Dipeptidyl-peptidase 4 Proteins 0.000 claims description 2
- 102000015696 Interleukins Human genes 0.000 claims description 2
- 108010063738 Interleukins Proteins 0.000 claims description 2
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 claims description 2
- 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
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 2
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 2
- 229960003121 arginine Drugs 0.000 claims description 2
- 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
- 229940092705 beclomethasone Drugs 0.000 claims description 2
- 229960004436 budesonide Drugs 0.000 claims description 2
- 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
- 229960002714 fluticasone Drugs 0.000 claims description 2
- MGNNYOODZCAHBA-GQKYHHCASA-N fluticasone Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@@H](C)[C@@](C(=O)SCF)(O)[C@@]2(C)C[C@@H]1O MGNNYOODZCAHBA-GQKYHHCASA-N 0.000 claims description 2
- 239000003112 inhibitor Substances 0.000 claims description 2
- 229940047122 interleukins Drugs 0.000 claims description 2
- FEWJPZIEWOKRBE-LWMBPPNESA-N levotartaric acid Chemical class OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 claims description 2
- 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
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-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
- 230000001078 anti-cholinergic effect Effects 0.000 claims 2
- 230000000510 mucolytic effect Effects 0.000 claims 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 101150061302 och1 gene Proteins 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 40
- 239000000243 solution Substances 0.000 description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
- 239000007787 solid Substances 0.000 description 21
- 235000019439 ethyl acetate Nutrition 0.000 description 19
- 238000009472 formulation Methods 0.000 description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000000443 aerosol Substances 0.000 description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 150000004702 methyl esters Chemical class 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004128 high performance liquid chromatography Methods 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
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- 102000005962 receptors Human genes 0.000 description 8
- 108020003175 receptors Proteins 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 108060003345 Adrenergic Receptor Proteins 0.000 description 7
- 102000017910 Adrenergic receptor Human genes 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 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 7
- 229960002848 formoterol Drugs 0.000 description 7
- 230000009870 specific binding Effects 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- GZDFHIJNHHMENY-UHFFFAOYSA-N Dimethyl dicarbonate Chemical compound COC(=O)OC(=O)OC GZDFHIJNHHMENY-UHFFFAOYSA-N 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 229940125782 compound 2 Drugs 0.000 description 5
- 239000006184 cosolvent Substances 0.000 description 5
- 235000010300 dimethyl dicarbonate Nutrition 0.000 description 5
- 239000004316 dimethyl dicarbonate Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
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- 239000000741 silica gel Substances 0.000 description 5
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- 239000000126 substance Substances 0.000 description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 4
- BPZSYCZIITTYBL-YJYMSZOUSA-N R-Formoterol Chemical compound C1=CC(OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-YJYMSZOUSA-N 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/26—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring
- C07C271/28—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a six-membered aromatic ring to a carbon atom of a non-condensed six-membered aromatic ring
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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
-
- 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
- A61P11/06—Antiasthmatics
-
- 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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
-
- 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
- C07B2200/07—Optical isomers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Epidemiology (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)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US96639107P | 2007-08-28 | 2007-08-28 | |
| US60/966,391 | 2007-08-28 | ||
| PCT/US2008/074643 WO2009029717A1 (en) | 2007-08-28 | 2008-08-28 | Carbamate stereoisomer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2008293444A1 AU2008293444A1 (en) | 2009-03-05 |
| AU2008293444B2 true AU2008293444B2 (en) | 2013-11-21 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2008293444A Ceased AU2008293444B2 (en) | 2007-08-28 | 2008-08-28 | Carbamate stereoisomer |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US7718822B2 (enExample) |
| EP (1) | EP2190813B1 (enExample) |
| JP (1) | JP5529740B2 (enExample) |
| KR (1) | KR20100065303A (enExample) |
| AR (1) | AR071045A1 (enExample) |
| AU (1) | AU2008293444B2 (enExample) |
| CA (1) | CA2696922C (enExample) |
| ES (1) | ES2430338T3 (enExample) |
| MX (1) | MX2010002039A (enExample) |
| NZ (1) | NZ583202A (enExample) |
| TW (1) | TWI465416B (enExample) |
| WO (1) | WO2009029717A1 (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN112279776B (zh) * | 2020-11-02 | 2022-09-02 | 扬州中宝药业股份有限公司 | 一种合成阿福特罗游离碱的方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3657319A (en) * | 1970-05-05 | 1972-04-18 | Smith Kline French Lab | Alpha-aminoalkyl-4-hydroxy-3-carboalkoxyaminobenzyl alcohols |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2115926C3 (de) | 1971-04-01 | 1978-05-03 | C.H. Boehringer Sohn, 6507 Ingelheim | 1 -(4-Hydroxy-3-dimethylaminosuIfamidophenyI)-2-aminoäthanderivate, Verfahren zu ihrer Herstellung und diese enthaltende Mittel |
| GB1415256A (en) | 1972-02-05 | 1975-11-26 | Yamanouchi Pharma Co Ltd | Alpha-aminomethylbenzyl alcohol derivatives |
| DE2305092A1 (de) | 1972-02-05 | 1973-08-16 | Yamanouchi Pharma Co Ltd | Alpha-aminomethylbenzylalkoholderivate |
| JPS4880523A (enExample) * | 1972-02-05 | 1973-10-29 | ||
| US3994974A (en) * | 1972-02-05 | 1976-11-30 | Yamanouchi Pharmaceutical Co., Ltd. | α-Aminomethylbenzyl alcohol derivatives |
| 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". |
| ES2208772T3 (es) | 1996-01-10 | 2004-06-16 | Asahi Kasei Kabushiki Kaisha | Nuevos compuestos triciclicos y compuestos farmaceuticos que contienen los mismos. |
| US6040344A (en) * | 1996-11-11 | 2000-03-21 | Sepracor Inc. | Formoterol process |
| DE69713374T2 (de) | 1996-11-11 | 2003-01-02 | Sepracor Inc., Marlborough | Verfahren zur herstellung von optisch reinen isomeren des formoterols |
| US6303145B2 (en) * | 1999-05-10 | 2001-10-16 | Sepracor Inc. | (S,R) formoterol methods and compositions |
| US20030145850A1 (en) * | 2000-03-01 | 2003-08-07 | Hailey Mark Andrew | Metered dose inhaler |
| 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 |
-
2008
- 2008-08-21 US US12/196,071 patent/US7718822B2/en active Active
- 2008-08-26 TW TW097132496A patent/TWI465416B/zh not_active IP Right Cessation
- 2008-08-27 AR ARP080103725A patent/AR071045A1/es unknown
- 2008-08-28 JP JP2010523135A patent/JP5529740B2/ja not_active Expired - Fee Related
- 2008-08-28 WO PCT/US2008/074643 patent/WO2009029717A1/en not_active Ceased
- 2008-08-28 NZ NZ583202A patent/NZ583202A/en not_active IP Right Cessation
- 2008-08-28 KR KR1020107004336A patent/KR20100065303A/ko not_active Ceased
- 2008-08-28 CA CA2696922A patent/CA2696922C/en active Active
- 2008-08-28 MX MX2010002039A patent/MX2010002039A/es active IP Right Grant
- 2008-08-28 AU AU2008293444A patent/AU2008293444B2/en not_active Ceased
- 2008-08-28 ES ES08828303T patent/ES2430338T3/es active Active
- 2008-08-28 EP EP08828303.1A patent/EP2190813B1/en not_active Not-in-force
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2010
- 2010-03-31 US US12/751,563 patent/US8173829B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3657319A (en) * | 1970-05-05 | 1972-04-18 | Smith Kline French Lab | Alpha-aminoalkyl-4-hydroxy-3-carboalkoxyaminobenzyl alcohols |
Also Published As
| Publication number | Publication date |
|---|---|
| US8173829B2 (en) | 2012-05-08 |
| CA2696922A1 (en) | 2009-03-05 |
| AR071045A1 (es) | 2010-05-26 |
| WO2009029717A1 (en) | 2009-03-05 |
| EP2190813A1 (en) | 2010-06-02 |
| KR20100065303A (ko) | 2010-06-16 |
| TWI465416B (zh) | 2014-12-21 |
| CA2696922C (en) | 2015-10-06 |
| US20090060917A1 (en) | 2009-03-05 |
| NZ583202A (en) | 2012-03-30 |
| JP2010538009A (ja) | 2010-12-09 |
| JP5529740B2 (ja) | 2014-06-25 |
| AU2008293444A1 (en) | 2009-03-05 |
| MX2010002039A (es) | 2010-03-25 |
| ES2430338T3 (es) | 2013-11-20 |
| US7718822B2 (en) | 2010-05-18 |
| US20100215589A1 (en) | 2010-08-26 |
| EP2190813B1 (en) | 2013-07-31 |
| TW200920725A (en) | 2009-05-16 |
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