TW200536814A - Chemical process and new crystalline form - Google Patents
Chemical process and new crystalline form Download PDFInfo
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- TW200536814A TW200536814A TW094110351A TW94110351A TW200536814A TW 200536814 A TW200536814 A TW 200536814A TW 094110351 A TW094110351 A TW 094110351A TW 94110351 A TW94110351 A TW 94110351A TW 200536814 A TW200536814 A TW 200536814A
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- acid
- compound
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- crystalline salt
- mixture
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- 238000001311 chemical methods and process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 99
- 150000003839 salts Chemical group 0.000 claims abstract description 75
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 31
- 239000000048 adrenergic agonist Substances 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 3
- 239000002253 acid Substances 0.000 claims description 72
- 239000000203 mixture Substances 0.000 claims description 71
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 38
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 26
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical class [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims description 18
- 239000013078 crystal Substances 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 14
- 238000010438 heat treatment Methods 0.000 claims description 13
- 239000000843 powder Substances 0.000 claims description 13
- 239000011780 sodium chloride Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 claims description 9
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- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims description 9
- 239000003246 corticosteroid Substances 0.000 claims description 8
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
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- 125000006239 protecting group Chemical group 0.000 claims description 8
- 239000000812 cholinergic antagonist Substances 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 5
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 230000005588 protonation Effects 0.000 claims description 4
- 208000024891 symptom Diseases 0.000 claims description 4
- 238000005349 anion exchange Methods 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
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- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
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- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
- OPFILOLCFWFBNT-UHFFFAOYSA-N 4-methyl-9h-fluorene Chemical compound C1C2=CC=CC=C2C2=C1C=CC=C2C OPFILOLCFWFBNT-UHFFFAOYSA-N 0.000 claims 1
- 150000007857 hydrazones Chemical class 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 8
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- 239000000243 solution Substances 0.000 description 31
- -1 monohydrogen salt Chemical class 0.000 description 30
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 28
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 21
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
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- 239000005557 antagonist Substances 0.000 description 10
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- 238000001914 filtration Methods 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 9
- 229910052782 aluminium Inorganic materials 0.000 description 9
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 9
- 238000002425 crystallisation Methods 0.000 description 9
- 230000008025 crystallization Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
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- 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 7
- 239000004480 active ingredient Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
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- 230000015572 biosynthetic process Effects 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 6
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 6
- 239000008101 lactose Substances 0.000 description 6
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- GUVUOGQBMYCBQP-UHFFFAOYSA-N dmpu Chemical compound CN1CCCN(C)C1=O GUVUOGQBMYCBQP-UHFFFAOYSA-N 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 4
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- 101100296720 Dictyostelium discoideum Pde4 gene Proteins 0.000 description 3
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- 230000001624 sedative effect Effects 0.000 description 1
- 238000007873 sieving Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 229940087562 sodium acetate trihydrate Drugs 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 229940046810 spiriva Drugs 0.000 description 1
- DQHNAVOVODVIMG-RGECMCKFSA-M spiriva Chemical compound [Br-].C([C@@H]1[N+]([C@H](C2)[C@@H]3[C@H]1O3)(C)C)C2OC(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 DQHNAVOVODVIMG-RGECMCKFSA-M 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229960000351 terfenadine Drugs 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- XZYMGRBAHIUVGY-UHFFFAOYSA-M tert-butyl(dimethyl)sulfanium;chloride Chemical compound [Cl-].C[S+](C)C(C)(C)C XZYMGRBAHIUVGY-UHFFFAOYSA-M 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 239000002753 trypsin inhibitor Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 238000004804 winding Methods 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
-
- 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
- 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
-
- 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
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0407521A GB0407521D0 (en) | 2004-04-02 | 2004-04-02 | Chemical process |
| GB0411688A GB0411688D0 (en) | 2004-05-25 | 2004-05-25 | Chemical process |
| US57446704P | 2004-05-26 | 2004-05-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW200536814A true TW200536814A (en) | 2005-11-16 |
Family
ID=34963396
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW094110351A TW200536814A (en) | 2004-04-02 | 2005-03-31 | Chemical process and new crystalline form |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7846973B2 (https=) |
| EP (1) | EP1730104A1 (https=) |
| JP (1) | JP2007530652A (https=) |
| AR (1) | AR052301A1 (https=) |
| AU (1) | AU2005227733A1 (https=) |
| BR (1) | BRPI0509382A (https=) |
| CA (1) | CA2561400A1 (https=) |
| IL (1) | IL178064A0 (https=) |
| MA (1) | MA28558B1 (https=) |
| NO (1) | NO20064884L (https=) |
| PE (1) | PE20060678A1 (https=) |
| TW (1) | TW200536814A (https=) |
| WO (1) | WO2005095328A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006066907A1 (en) * | 2004-12-21 | 2006-06-29 | Glaxo Group Limited | Pharmaceutical formulations |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| MX2010007604A (es) | 2008-01-11 | 2010-08-02 | Novartis Ag | Pirimidinas como inhibidores de cinasa. |
| WO2011061527A1 (en) | 2009-11-17 | 2011-05-26 | Astrazeneca Ab | Combinations comprising a glucocorticoid receptor modulator for the treatment of respiratory diseases |
| IT1399912B1 (it) * | 2010-04-29 | 2013-05-09 | Lundbeck Pharmaceuticals Italy S Pa | Processo di preparazione di ritodrina cloridrato. |
| JP5645762B2 (ja) * | 2010-06-29 | 2014-12-24 | 日本ポリプロ株式会社 | ポリオレフィンの結晶性分布分析方法およびその装置 |
| WO2012034095A1 (en) | 2010-09-09 | 2012-03-15 | Irm Llc | Compounds and compositions as trk inhibitors |
| US8637516B2 (en) | 2010-09-09 | 2014-01-28 | Irm Llc | Compounds and compositions as TRK inhibitors |
| WO2012116217A1 (en) | 2011-02-25 | 2012-08-30 | Irm Llc | Compounds and compositions as trk inhibitors |
| GB201212081D0 (en) * | 2012-07-06 | 2012-08-22 | Kalvista Pharmaceuticals Ltd | New polymorph |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2064336B (en) | 1979-12-06 | 1984-03-14 | Glaxo Group Ltd | Device for dispensing medicaments |
| US4353656A (en) | 1980-10-14 | 1982-10-12 | Xerox Corporation | Moving coil, multiple energy print hammer system including a closed loop servo |
| DE3274065D1 (de) | 1981-07-08 | 1986-12-11 | Draco Ab | Powder inhalator |
| GB2169265B (en) | 1982-10-08 | 1987-08-12 | Glaxo Group Ltd | Pack for medicament |
| US4778054A (en) | 1982-10-08 | 1988-10-18 | Glaxo Group Limited | Pack for administering medicaments to patients |
| DK172541B1 (da) | 1982-10-08 | 1998-12-07 | Glaxo Group Ltd | Apparat til administrering af medikamenter til patienter og en medikamentpakning til brug i apparatet |
| DE3682457D1 (de) | 1985-07-30 | 1991-12-19 | Glaxo Group Ltd | Geraet zur verabreichung von medikamenten an patienten. |
| GB9004781D0 (en) | 1990-03-02 | 1990-04-25 | Glaxo Group Ltd | Device |
| HU225869B1 (en) | 1992-04-02 | 2007-11-28 | Smithkline Beecham Corp | Compounds with antiallergic and antiinflammatory activity and pharmaceutical compns. contg. them |
| US5495054A (en) | 1994-05-31 | 1996-02-27 | Sepracor, Inc. | Tetrahydroindeno[1,2-D][1,3,2]oxazaboroles and their use as enantioselective catalysts |
| US6040344A (en) | 1996-11-11 | 2000-03-21 | Sepracor Inc. | Formoterol process |
| GB9700226D0 (en) | 1997-01-08 | 1997-02-26 | Glaxo Group Ltd | Inhalation device |
| UA73965C2 (en) | 1999-12-08 | 2005-10-17 | Theravance Inc | b2 ADRENERGIC RECEPTOR ANTAGONISTS |
| OA11558A (en) | 1999-12-08 | 2004-06-03 | Advanced Medicine Inc | Beta 2-adrenergic receptor agonists. |
| US6632666B2 (en) | 2000-01-14 | 2003-10-14 | Biolife Solutions, Inc. | Normothermic, hypothermic and cryopreservation maintenance and storage of cells, tissues and organs in gel-based media |
| TWI249515B (en) * | 2001-11-13 | 2006-02-21 | Theravance Inc | Aryl aniline beta2 adrenergic receptor agonists |
| GB0201677D0 (en) | 2002-01-25 | 2002-03-13 | Glaxo Group Ltd | Medicament dispenser |
| AR040661A1 (es) * | 2002-07-26 | 2005-04-13 | Theravance Inc | Diclorhidrato cristalino de n-{2-[-((r)-2-hidroxi-2-feniletilamino)fenil]etil}-(r)-2hidroxi-2-(3-formamido-4-hidroxifenil)etilamina, agonista del receptor adrenergico beta 2 |
| CN100387598C (zh) | 2002-09-16 | 2008-05-14 | 葛兰素集团有限公司 | 吡唑并[3,4-b]吡啶化合物及其作为磷酸二酯酶抑制剂的用途 |
| TW200510277A (en) | 2003-05-27 | 2005-03-16 | Theravance Inc | Crystalline form of β2-adrenergic receptor agonist |
-
2005
- 2005-03-30 WO PCT/GB2005/001241 patent/WO2005095328A1/en not_active Ceased
- 2005-03-30 JP JP2007505632A patent/JP2007530652A/ja active Pending
- 2005-03-30 US US10/599,145 patent/US7846973B2/en not_active Expired - Fee Related
- 2005-03-30 CA CA002561400A patent/CA2561400A1/en not_active Abandoned
- 2005-03-30 AU AU2005227733A patent/AU2005227733A1/en not_active Abandoned
- 2005-03-30 BR BRPI0509382-1A patent/BRPI0509382A/pt not_active IP Right Cessation
- 2005-03-30 EP EP05729685A patent/EP1730104A1/en not_active Withdrawn
- 2005-03-31 PE PE2005000372A patent/PE20060678A1/es not_active Application Discontinuation
- 2005-03-31 TW TW094110351A patent/TW200536814A/zh unknown
- 2005-03-31 AR ARP050101278A patent/AR052301A1/es not_active Application Discontinuation
-
2006
- 2006-09-13 IL IL178064A patent/IL178064A0/en unknown
- 2006-10-26 NO NO20064884A patent/NO20064884L/no not_active Application Discontinuation
- 2006-10-30 MA MA29421A patent/MA28558B1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2561400A1 (en) | 2005-10-13 |
| PE20060678A1 (es) | 2006-08-02 |
| WO2005095328A1 (en) | 2005-10-13 |
| KR20070000508A (ko) | 2007-01-02 |
| JP2007530652A (ja) | 2007-11-01 |
| US7846973B2 (en) | 2010-12-07 |
| MA28558B1 (fr) | 2007-04-03 |
| NO20064884L (no) | 2006-10-26 |
| BRPI0509382A (pt) | 2007-09-18 |
| EP1730104A1 (en) | 2006-12-13 |
| IL178064A0 (en) | 2006-12-31 |
| US20100063157A1 (en) | 2010-03-11 |
| AR052301A1 (es) | 2007-03-14 |
| AU2005227733A1 (en) | 2005-10-13 |
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