CA2650631A1 - Crystalline forms of a dimethylphenyl compound - Google Patents
Crystalline forms of a dimethylphenyl compound Download PDFInfo
- Publication number
- CA2650631A1 CA2650631A1 CA002650631A CA2650631A CA2650631A1 CA 2650631 A1 CA2650631 A1 CA 2650631A1 CA 002650631 A CA002650631 A CA 002650631A CA 2650631 A CA2650631 A CA 2650631A CA 2650631 A1 CA2650631 A1 CA 2650631A1
- Authority
- CA
- Canada
- Prior art keywords
- free base
- crystalline free
- base form
- biphenyl
- ethyl
- 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
- -1 dimethylphenyl compound Chemical class 0.000 title description 20
- 239000012458 free base Substances 0.000 claims abstract description 141
- 238000000034 method Methods 0.000 claims abstract description 59
- ABKYKPJDWBZALL-QNGWXLTQSA-N [1-[3-[4-[[[(2r)-2-(3-formamido-4-hydroxyphenyl)-2-hydroxyethyl]amino]methyl]-2,5-dimethylanilino]-3-oxopropyl]piperidin-4-yl] n-(2-phenylphenyl)carbamate Chemical compound CC=1C=C(CNC[C@H](O)C=2C=C(NC=O)C(O)=CC=2)C(C)=CC=1NC(=O)CCN(CC1)CCC1OC(=O)NC1=CC=CC=C1C1=CC=CC=C1 ABKYKPJDWBZALL-QNGWXLTQSA-N 0.000 claims abstract description 57
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 48
- 208000019693 Lung disease Diseases 0.000 claims abstract description 16
- 230000008569 process Effects 0.000 claims abstract description 13
- 239000003814 drug Substances 0.000 claims description 62
- 229940124597 therapeutic agent Drugs 0.000 claims description 59
- 239000002904 solvent Substances 0.000 claims description 42
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 22
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 21
- 108060003345 Adrenergic Receptor Proteins 0.000 claims description 17
- 102000017910 Adrenergic receptor Human genes 0.000 claims description 17
- 239000013078 crystal Substances 0.000 claims description 16
- 239000002294 steroidal antiinflammatory agent Substances 0.000 claims description 13
- 239000003937 drug carrier Substances 0.000 claims description 12
- 241000124008 Mammalia Species 0.000 claims description 11
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 10
- 239000003085 diluting agent Substances 0.000 claims description 10
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims description 9
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 9
- 238000011282 treatment Methods 0.000 claims description 9
- 230000007883 bronchodilation Effects 0.000 claims description 8
- 208000006673 asthma Diseases 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 230000003042 antagnostic effect Effects 0.000 claims description 2
- 239000012453 solvate Substances 0.000 abstract description 18
- 239000000543 intermediate Substances 0.000 abstract description 3
- 239000000203 mixture Substances 0.000 description 146
- 150000001875 compounds Chemical class 0.000 description 116
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 90
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 57
- 238000003556 assay Methods 0.000 description 49
- 239000000243 solution Substances 0.000 description 47
- 210000004027 cell Anatomy 0.000 description 42
- 238000012360 testing method Methods 0.000 description 40
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 29
- 239000002002 slurry Substances 0.000 description 29
- 239000007787 solid Substances 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 102000005962 receptors Human genes 0.000 description 24
- 108020003175 receptors Proteins 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 23
- RSDOPYMFZBJHRL-UHFFFAOYSA-N Oxotremorine Chemical compound O=C1CCCN1CC#CCN1CCCC1 RSDOPYMFZBJHRL-UHFFFAOYSA-N 0.000 description 23
- 235000019441 ethanol Nutrition 0.000 description 22
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- 239000012044 organic layer Substances 0.000 description 20
- 239000012528 membrane Substances 0.000 description 19
- 239000011541 reaction mixture Substances 0.000 description 17
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 16
- 239000002245 particle Substances 0.000 description 16
- 239000000725 suspension Substances 0.000 description 16
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 15
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 14
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- 238000009739 binding Methods 0.000 description 13
- 239000000872 buffer Substances 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 238000001914 filtration Methods 0.000 description 13
- QMOVGVNKXUTCQU-UHFFFAOYSA-N (2-phenylphenyl)carbamic acid Chemical compound OC(=O)NC1=CC=CC=C1C1=CC=CC=C1 QMOVGVNKXUTCQU-UHFFFAOYSA-N 0.000 description 12
- 239000000556 agonist Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 239000006199 nebulizer Substances 0.000 description 12
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 12
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 12
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 11
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
- 230000027455 binding Effects 0.000 description 11
- 239000012267 brine Substances 0.000 description 11
- 239000008101 lactose Substances 0.000 description 11
- 229940071648 metered dose inhaler Drugs 0.000 description 11
- 239000012071 phase Substances 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 10
- 235000017557 sodium bicarbonate Nutrition 0.000 description 10
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 239000002775 capsule Substances 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 9
- 239000012065 filter cake Substances 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- NZWOPGCLSHLLPA-UHFFFAOYSA-N methacholine Chemical compound C[N+](C)(C)CC(C)OC(C)=O NZWOPGCLSHLLPA-UHFFFAOYSA-N 0.000 description 9
- 229960002329 methacholine Drugs 0.000 description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
- 239000008188 pellet Substances 0.000 description 9
- 239000000546 pharmaceutical excipient Substances 0.000 description 9
- 229920006395 saturated elastomer Polymers 0.000 description 9
- 238000002411 thermogravimetry Methods 0.000 description 9
- OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 description 8
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 8
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- 239000004044 bronchoconstricting agent Substances 0.000 description 8
- 230000003435 bronchoconstrictive effect Effects 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- 231100000673 dose–response relationship Toxicity 0.000 description 8
- 229940112141 dry powder inhaler Drugs 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 8
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 8
- 230000001404 mediated effect Effects 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical class CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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 7
- 239000000048 adrenergic agonist Substances 0.000 description 7
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- 238000004128 high performance liquid chromatography Methods 0.000 description 7
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- 230000005764 inhibitory process Effects 0.000 description 7
- 239000003149 muscarinic antagonist Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
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- AGZCCVMWUZINGV-UHFFFAOYSA-N piperidin-4-yl n-(2-phenylphenyl)carbamate Chemical compound C1CNCCC1OC(=O)NC1=CC=CC=C1C1=CC=CC=C1 AGZCCVMWUZINGV-UHFFFAOYSA-N 0.000 description 6
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- OXDZCSKGGZZWHZ-WBCKFURZSA-N [1-[3-[4-[[[(2r)-2-[tert-butyl(dimethyl)silyl]oxy-2-(3-formamido-4-hydroxyphenyl)ethyl]amino]methyl]-2,5-dimethylanilino]-3-oxopropyl]piperidin-4-yl] n-(2-phenylphenyl)carbamate Chemical compound CC=1C=C(CNC[C@H](O[Si](C)(C)C(C)(C)C)C=2C=C(NC=O)C(O)=CC=2)C(C)=CC=1NC(=O)CCN(CC1)CCC1OC(=O)NC1=CC=CC=C1C1=CC=CC=C1 OXDZCSKGGZZWHZ-WBCKFURZSA-N 0.000 description 5
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US79470906P | 2006-04-25 | 2006-04-25 | |
| US60/794,709 | 2006-04-25 | ||
| PCT/US2007/010120 WO2007127297A2 (en) | 2006-04-25 | 2007-04-24 | Crystalline forms of a dimethylphenyl compound |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2650631A1 true CA2650631A1 (en) | 2007-11-08 |
Family
ID=38556280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002650631A Abandoned CA2650631A1 (en) | 2006-04-25 | 2007-04-24 | Crystalline forms of a dimethylphenyl compound |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US7880010B2 (https=) |
| EP (1) | EP2010490B1 (https=) |
| JP (1) | JP2009535340A (https=) |
| CN (1) | CN101426765A (https=) |
| AR (1) | AR060648A1 (https=) |
| AT (1) | ATE520660T1 (https=) |
| CA (1) | CA2650631A1 (https=) |
| PE (1) | PE20080195A1 (https=) |
| TW (1) | TW200811104A (https=) |
| WO (1) | WO2007127297A2 (https=) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6693202B1 (en) * | 1999-02-16 | 2004-02-17 | Theravance, Inc. | Muscarinic receptor antagonists |
| PE20040950A1 (es) | 2003-02-14 | 2005-01-01 | Theravance Inc | DERIVADOS DE BIFENILO COMO AGONISTAS DE LOS RECEPTORES ADRENERGICOS ß2 Y COMO ANTAGONISTAS DE LOS RECEPTORES MUSCARINICOS |
| WO2004073729A1 (ja) | 2003-02-21 | 2004-09-02 | Translational Research Ltd. | 薬物の経鼻投与用組成物 |
| CA2519287A1 (en) | 2003-03-27 | 2004-10-14 | Bioactis Limited | Powder medicine applicator for nasal cavity |
| WO2006016530A1 (ja) * | 2004-08-10 | 2006-02-16 | Translational Research, Ltd. | 速効性でかつ高い吸収性を可能とする経鼻投与用組成物 |
| JP2008510014A (ja) * | 2004-08-16 | 2008-04-03 | セラヴァンス， インコーポレーテッド | β２アドレナリン作用性レセプターアゴニスト活性およびムスカリン性レセプターアンタゴニスト活性を有する化合物 |
| TW200811105A (en) * | 2006-04-25 | 2008-03-01 | Theravance Inc | Dialkylphenyl compounds having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
| US20080071141A1 (en) * | 2006-09-18 | 2008-03-20 | Abhisuek Gattani | Method and apparatus for measuring attributes of an anatomical feature during a medical procedure |
| CN101668544B (zh) | 2006-12-26 | 2013-04-24 | 株式会社新日本科学 | 经鼻投用制剂 |
| US20090216010A1 (en) * | 2008-02-22 | 2009-08-27 | Wei-Hong Tseng | Crystalline carbapenem compound and produced method thereof |
| SG175023A1 (en) * | 2009-04-14 | 2011-11-28 | Glaxo Group Ltd | Process for the preparation of a biphenyl-2-ylcarbamic acid ester |
| SG175330A1 (en) | 2009-04-23 | 2011-11-28 | Theravance Inc | DIAMIDE COMPOUNDS HAVING MUSCARINIC RECEPTOR ANTAGONIST AND ß2 ADRENERGIC RECEPTOR AGONIST ACTIVITY |
| US9101539B2 (en) * | 2009-05-15 | 2015-08-11 | Shin Nippon Biomedical Laboratories, Ltd. | Intranasal pharmaceutical compositions with improved pharmacokinetics |
| GB2472327B (en) | 2009-07-31 | 2013-03-13 | Shin Nippon Biomedical Lab Ltd | Intranasal granisetron and nasal applicator |
| WO2011081937A1 (en) | 2009-12-15 | 2011-07-07 | Gilead Sciences, Inc. | Corticosteroid-beta-agonist-muscarinic antagonist compounds for use in therapy |
| EP2386555A1 (en) | 2010-05-13 | 2011-11-16 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and m3 muscarinic antagonist activities |
| AR083115A1 (es) | 2010-09-30 | 2013-01-30 | Theravance Inc | Sales oxalato cristalinas de un compuesto diamida |
| EP2592078A1 (en) | 2011-11-11 | 2013-05-15 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and M3 muscarinic antagonist activities |
| EP2592077A1 (en) | 2011-11-11 | 2013-05-15 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and M3 muscarinic antagonist activities |
| WO2014175234A1 (ja) * | 2013-04-26 | 2014-10-30 | 富士フイルム株式会社 | 撮像装置及び画像表示方法 |
| CN107108502A (zh) * | 2015-05-14 | 2017-08-29 | 四川海思科制药有限公司 | 具有β2受体激动及M受体拮抗活性的联苯衍生物及其在医药上的用途 |
| US11744967B2 (en) | 2017-09-26 | 2023-09-05 | Shin Nippon Biomedical Laboratories, Ltd. | Intranasal delivery devices |
Family Cites Families (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995006635A1 (en) | 1993-09-02 | 1995-03-09 | Yamanouchi Pharmaceutical Co., Ltd. | Carbamate derivative and medicine containing the same |
| WO1995021820A1 (en) | 1994-02-10 | 1995-08-17 | Yamanouchi Pharmaceutical Co., Ltd. | Novel carbamate derivative and medicinal composition containing the same |
| US6040344A (en) * | 1996-11-11 | 2000-03-21 | Sepracor Inc. | Formoterol process |
| US6693202B1 (en) * | 1999-02-16 | 2004-02-17 | Theravance, Inc. | Muscarinic receptor antagonists |
| UA73965C2 (en) * | 1999-12-08 | 2005-10-17 | Theravance Inc | b2 ADRENERGIC RECEPTOR ANTAGONISTS |
| US20030018019A1 (en) * | 2001-06-23 | 2003-01-23 | Boehringer Ingelheim Pharma Kg | Pharmaceutical compositions based on anticholinergics, corticosteroids and betamimetics |
| TWI249515B (en) * | 2001-11-13 | 2006-02-21 | Theravance Inc | Aryl aniline beta2 adrenergic receptor agonists |
| US6653323B2 (en) * | 2001-11-13 | 2003-11-25 | Theravance, Inc. | Aryl aniline β2 adrenergic receptor agonists |
| PE20040950A1 (es) * | 2003-02-14 | 2005-01-01 | Theravance Inc | DERIVADOS DE BIFENILO COMO AGONISTAS DE LOS RECEPTORES ADRENERGICOS ß2 Y COMO ANTAGONISTAS DE LOS RECEPTORES MUSCARINICOS |
| WO2004101525A1 (en) * | 2003-05-08 | 2004-11-25 | Theravance, Inc. | Crystalline form of aryl aniline beta-2 adrenergic receptor agonist |
| US7345060B2 (en) * | 2003-11-21 | 2008-03-18 | Theravance, Inc. | Compounds having β2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
| JP2008510014A (ja) * | 2004-08-16 | 2008-04-03 | セラヴァンス， インコーポレーテッド | β２アドレナリン作用性レセプターアゴニスト活性およびムスカリン性レセプターアンタゴニスト活性を有する化合物 |
| TWI374883B (en) * | 2004-08-16 | 2012-10-21 | Theravance Inc | Crystalline form of a biphenyl compound |
| US7569586B2 (en) * | 2004-08-16 | 2009-08-04 | Theravance, Inc. | Compounds having β2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
| US7558576B2 (en) * | 2005-03-29 | 2009-07-07 | Qualcomm Incorporated | Employing frequency offset to compensate for Doppler shift |
| TW200811105A (en) * | 2006-04-25 | 2008-03-01 | Theravance Inc | Dialkylphenyl compounds having beta2 adrenergic receptor agonist and muscarinic receptor antagonist activity |
-
2007
- 2007-04-23 TW TW096114174A patent/TW200811104A/zh unknown
- 2007-04-24 AT AT07794375T patent/ATE520660T1/de not_active IP Right Cessation
- 2007-04-24 JP JP2009507797A patent/JP2009535340A/ja active Pending
- 2007-04-24 US US11/789,154 patent/US7880010B2/en not_active Expired - Fee Related
- 2007-04-24 PE PE2007000508A patent/PE20080195A1/es not_active Application Discontinuation
- 2007-04-24 AR ARP070101778A patent/AR060648A1/es unknown
- 2007-04-24 WO PCT/US2007/010120 patent/WO2007127297A2/en not_active Ceased
- 2007-04-24 CN CNA2007800142180A patent/CN101426765A/zh active Pending
- 2007-04-24 CA CA002650631A patent/CA2650631A1/en not_active Abandoned
- 2007-04-24 EP EP07794375A patent/EP2010490B1/en active Active
-
2010
- 2010-12-16 US US12/970,013 patent/US20110086881A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007127297A2 (en) | 2007-11-08 |
| WO2007127297A3 (en) | 2007-12-21 |
| PE20080195A1 (es) | 2008-04-04 |
| ATE520660T1 (de) | 2011-09-15 |
| US7880010B2 (en) | 2011-02-01 |
| US20070249674A1 (en) | 2007-10-25 |
| EP2010490A2 (en) | 2009-01-07 |
| EP2010490B1 (en) | 2011-08-17 |
| TW200811104A (en) | 2008-03-01 |
| JP2009535340A (ja) | 2009-10-01 |
| US20110086881A1 (en) | 2011-04-14 |
| CN101426765A (zh) | 2009-05-06 |
| AR060648A1 (es) | 2008-07-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |