CA3165243A1 - Crystalline aclidinium bromide and uses thereof - Google Patents
Crystalline aclidinium bromide and uses thereof Download PDFInfo
- Publication number
- CA3165243A1 CA3165243A1 CA3165243A CA3165243A CA3165243A1 CA 3165243 A1 CA3165243 A1 CA 3165243A1 CA 3165243 A CA3165243 A CA 3165243A CA 3165243 A CA3165243 A CA 3165243A CA 3165243 A1 CA3165243 A1 CA 3165243A1
- Authority
- CA
- Canada
- Prior art keywords
- aclidinium bromide
- pharmaceutical composition
- crystalline
- mixture
- bromide
- 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.)
- Pending
Links
- 229960005012 aclidinium bromide Drugs 0.000 title claims abstract description 62
- ASMXXROZKSBQIH-VITNCHFBSA-N aclidinium Chemical compound C([C@@H](C(CC1)CC2)OC(=O)C(O)(C=3SC=CC=3)C=3SC=CC=3)[N+]21CCCOC1=CC=CC=C1 ASMXXROZKSBQIH-VITNCHFBSA-N 0.000 title claims abstract description 27
- 239000000843 powder Substances 0.000 claims abstract description 23
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 10
- 239000003814 drug Substances 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 30
- 239000000725 suspension Substances 0.000 claims description 21
- 239000000243 solution Substances 0.000 claims description 13
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N lactose group Chemical group OC1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@@H](O)[C@H](O2)CO)[C@H](O1)CO GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- WSVLPVUVIUVCRA-KPKNDVKVSA-N Alpha-lactose monohydrate Chemical compound O.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 WSVLPVUVIUVCRA-KPKNDVKVSA-N 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 3
- 229960001375 lactose Drugs 0.000 claims description 3
- 239000008101 lactose Substances 0.000 claims description 3
- 230000004580 weight loss Effects 0.000 claims description 3
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- XLAKJQPTOJHYDR-QTQXQZBYSA-M aclidinium bromide Chemical compound [Br-].C([C@@H](C(CC1)CC2)OC(=O)C(O)(C=3SC=CC=3)C=3SC=CC=3)[N+]21CCCOC1=CC=CC=C1 XLAKJQPTOJHYDR-QTQXQZBYSA-M 0.000 description 47
- 239000002904 solvent Substances 0.000 description 36
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 23
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 20
- NIDWUZTTXGJFNN-UHFFFAOYSA-N 3-bromopropoxybenzene Chemical compound BrCCCOC1=CC=CC=C1 NIDWUZTTXGJFNN-UHFFFAOYSA-N 0.000 description 14
- 239000002245 particle Substances 0.000 description 13
- 238000004128 high performance liquid chromatography Methods 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 8
- 238000005956 quaternization reaction Methods 0.000 description 7
- 238000002411 thermogravimetry Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 229940019903 aclidinium Drugs 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 6
- 238000004626 scanning electron microscopy Methods 0.000 description 6
- 238000001694 spray drying Methods 0.000 description 6
- FVEJUHUCFCAYRP-UHFFFAOYSA-N 2-hydroxy-2,2-dithiophen-2-ylacetic acid Chemical compound C=1C=CSC=1C(O)(C(=O)O)C1=CC=CS1 FVEJUHUCFCAYRP-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 5
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- SYHWYWHVEQQDMO-UHFFFAOYSA-N methyl 2-hydroxy-2,2-dithiophen-2-ylacetate Chemical compound C=1C=CSC=1C(O)(C(=O)OC)C1=CC=CS1 SYHWYWHVEQQDMO-UHFFFAOYSA-N 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 125000003375 sulfoxide group Chemical group 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- GYDFTKNRHZMENP-ZDUSSCGKSA-N [(3r)-1-azabicyclo[2.2.2]octan-3-yl] 2-hydroxy-2,2-dithiophen-2-ylacetate Chemical compound O([C@@H]1C2CCN(CC2)C1)C(=O)C(O)(C=1SC=CC=1)C1=CC=CS1 GYDFTKNRHZMENP-ZDUSSCGKSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000000113 differential scanning calorimetry Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 231100000024 genotoxic Toxicity 0.000 description 3
- 230000001738 genotoxic effect Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- AZXLOLRTEJEZHJ-UHFFFAOYSA-N 3-chloropropoxybenzene Chemical compound ClCCCOC1=CC=CC=C1 AZXLOLRTEJEZHJ-UHFFFAOYSA-N 0.000 description 1
- -1 3-phenoxypropyl Chemical group 0.000 description 1
- 101100532856 Arabidopsis thaliana SDRA gene Proteins 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- 229910016523 CuKa Inorganic materials 0.000 description 1
- 241000248317 Didinium Species 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 1
- 108050003473 Muscarinic acetylcholine receptor Proteins 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- 244000126002 Ziziphus vulgaris Species 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229910002056 binary alloy Inorganic materials 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 230000007885 bronchoconstriction Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000013480 data collection Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000003086 effect on acetylcholine Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 238000010902 jet-milling Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 239000003149 muscarinic antagonist Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 238000004621 scanning probe microscopy Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- KKVTYAVXTDIPAP-UHFFFAOYSA-M sodium;methanesulfonate Chemical compound [Na+].CS([O-])(=O)=O KKVTYAVXTDIPAP-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- 229940020597 tudorza Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- 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
- A61K31/439—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 the ring forming part of a bridged ring system, e.g. quinuclidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/0018—Evaporation of components of the mixture to be separated
- B01D9/0027—Evaporation of components of the mixture to be separated by means of conveying fluid, e.g. spray-crystallisation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01D—SEPARATION
- B01D9/00—Crystallisation
- B01D9/005—Selection of auxiliary, e.g. for control of crystallisation nuclei, of crystal growth, of adherence to walls; Arrangements for introduction thereof
-
- 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)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Pulmonology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Otolaryngology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Catalysts (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PT108370 | 2015-03-30 | ||
| PT10837015A PT108370B (pt) | 2015-03-30 | 2015-03-30 | Processo de preparação de brometo de aclidínio |
| CA2980665A CA2980665A1 (en) | 2015-03-30 | 2016-03-30 | Process for the preparation of aclidinium bromide |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2980665A Division CA2980665A1 (en) | 2015-03-30 | 2016-03-30 | Process for the preparation of aclidinium bromide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA3165243A1 true CA3165243A1 (en) | 2016-10-06 |
Family
ID=55806548
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2980665A Pending CA2980665A1 (en) | 2015-03-30 | 2016-03-30 | Process for the preparation of aclidinium bromide |
| CA3165243A Pending CA3165243A1 (en) | 2015-03-30 | 2016-03-30 | Crystalline aclidinium bromide and uses thereof |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2980665A Pending CA2980665A1 (en) | 2015-03-30 | 2016-03-30 | Process for the preparation of aclidinium bromide |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US10087177B2 (enExample) |
| EP (1) | EP3277679A1 (enExample) |
| JP (4) | JP2018510189A (enExample) |
| CN (1) | CN108112252B (enExample) |
| AU (1) | AU2016240289B2 (enExample) |
| CA (2) | CA2980665A1 (enExample) |
| IL (1) | IL254712A0 (enExample) |
| PT (1) | PT108370B (enExample) |
| WO (1) | WO2016156836A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT108370B (pt) | 2015-03-30 | 2018-10-25 | Hovione Farm S A | Processo de preparação de brometo de aclidínio |
| CN108586450B (zh) * | 2017-12-15 | 2021-02-19 | 上海方予健康医药科技有限公司 | 一种胆碱m受体抗结剂的重结晶纯化方法 |
| PT115583B (pt) * | 2019-06-17 | 2022-05-02 | Hovione Farm S A | Processo contínuo para a preparação de medicamentos anticolinérgicos |
| CN114890997A (zh) * | 2022-04-20 | 2022-08-12 | 江苏联环药业股份有限公司 | 一种抗胆碱能药物噻格溴铵的制备工艺 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2165768B1 (es) * | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| NZ519984A (en) * | 2000-01-07 | 2004-03-26 | Transform Pharmaceuticals Inc | High-throughput formation, identification, and analysis of diverse solid-forms |
| US6482847B2 (en) * | 2000-10-03 | 2002-11-19 | Hoffmann-La Roche Inc. | Amorphous form of cell cycle inhibitor having improved solubility and bioavailability |
| AR044134A1 (es) * | 2003-05-02 | 2005-08-24 | Novartis Ag | Derivados de quinuclidina, metodo de preparacion y composiciones farmaceuticas. |
| BRPI0413129A (pt) | 2003-07-29 | 2006-10-03 | Boehringer Ingelheim Int | medicamentos para inalação compreendendo betamiméticos e anticolinérgico |
| CA2635581C (en) * | 2005-12-28 | 2017-02-28 | Vertex Pharmaceuticals Incorporated | Solid forms of n-[2,4-bis(1,1-dimethylethyl)-5-hydroxyphenyl]-1,4-dihydro-4-oxoquinoline-3-carboxamide |
| ES2298049B1 (es) * | 2006-07-21 | 2009-10-20 | Laboratorios Almirall S.A. | Procedimiento para fabricar bromuro de 3(r)-(2-hidroxi-2,2-ditien-2-ilacetoxi)-1-(3-fenoxipropil)-1-azoniabiciclo (2.2.2) octano. |
| US9273001B2 (en) * | 2012-08-15 | 2016-03-01 | Glaxo Group Limited | Chemical process |
| CZ306791B6 (cs) * | 2013-10-29 | 2017-07-12 | Zentiva, K.S. | Průmyslově využitelný způsob přípravy aklidinium bromidu o vysoké čistotě |
| WO2015071824A1 (en) | 2013-11-13 | 2015-05-21 | Glenmark Pharmaceuticals Limited; Glenmark Generics Limited | Process for the preparation of aclidinium bromide |
| PT108370B (pt) | 2015-03-30 | 2018-10-25 | Hovione Farm S A | Processo de preparação de brometo de aclidínio |
-
2015
- 2015-03-30 PT PT10837015A patent/PT108370B/pt active IP Right Grant
-
2016
- 2016-03-30 JP JP2017551330A patent/JP2018510189A/ja active Pending
- 2016-03-30 AU AU2016240289A patent/AU2016240289B2/en not_active Ceased
- 2016-03-30 WO PCT/GB2016/050888 patent/WO2016156836A1/en not_active Ceased
- 2016-03-30 US US15/562,814 patent/US10087177B2/en active Active
- 2016-03-30 EP EP16717989.4A patent/EP3277679A1/en not_active Withdrawn
- 2016-03-30 CA CA2980665A patent/CA2980665A1/en active Pending
- 2016-03-30 CA CA3165243A patent/CA3165243A1/en active Pending
- 2016-03-30 CN CN201680031574.2A patent/CN108112252B/zh not_active Expired - Fee Related
-
2017
- 2017-09-26 IL IL254712A patent/IL254712A0/en unknown
-
2018
- 2018-08-28 US US16/114,714 patent/US10590124B2/en not_active Expired - Fee Related
-
2020
- 2020-06-04 JP JP2020097781A patent/JP2020143160A/ja active Pending
- 2020-11-05 JP JP2020185042A patent/JP7124035B2/ja active Active
-
2022
- 2022-08-10 JP JP2022128244A patent/JP2022160667A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| EP3277679A1 (en) | 2018-02-07 |
| US10590124B2 (en) | 2020-03-17 |
| JP2020143160A (ja) | 2020-09-10 |
| US20180362523A1 (en) | 2018-12-20 |
| JP2021020965A (ja) | 2021-02-18 |
| PT108370B (pt) | 2018-10-25 |
| CN108112252B (zh) | 2020-11-24 |
| PT108370A (pt) | 2016-09-30 |
| US10087177B2 (en) | 2018-10-02 |
| IL254712A0 (en) | 2017-11-30 |
| CA2980665A1 (en) | 2016-10-06 |
| AU2016240289B2 (en) | 2020-08-27 |
| US20180105517A1 (en) | 2018-04-19 |
| WO2016156836A1 (en) | 2016-10-06 |
| JP2022160667A (ja) | 2022-10-19 |
| JP2018510189A (ja) | 2018-04-12 |
| JP7124035B2 (ja) | 2022-08-23 |
| AU2016240289A1 (en) | 2017-10-19 |
| CN108112252A (zh) | 2018-06-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP7124035B2 (ja) | アクリジニウム臭化物の製造方法 | |
| CN104144928B (zh) | 制备噻托溴铵的方法 | |
| EP2882753B1 (en) | Process for the preparation of pemetrexed and lysin salt thereof | |
| KR20240027877A (ko) | 2,4,6-트리플루오로-n-[6-(1-메틸-피페리딘-4-카르보닐)-피리딘-2-일]-벤즈아미드헤미숙시네이트의 대규모 제조를 위한 방법 및 중간체, 및 2,4,6-트리플루오로-n-[6-(1-메틸-피페리딘-4-카르보닐)-피리딘-2-일]-벤즈아미드 아세테이트의 제조 | |
| WO2015011659A1 (en) | Crystalline polymorphic forms of regorafenib and processes for the preparation of polymorph i of regorafenib | |
| JP2018510189A5 (enExample) | ||
| CN108586450B (zh) | 一种胆碱m受体抗结剂的重结晶纯化方法 | |
| JP2014201592A (ja) | 臭化チオトロピウムの結晶形態 | |
| JP2012500268A (ja) | ７−クロロ−Ｎ，Ｎ，５−トリメチル−４−オキソ−３−フェニル−３，５−ジヒドロ−４Ｈ−ピリダジノ［４，５−ｂ］インドール−１−アセトアミドの多形体を製造するための方法 | |
| EP3052499B1 (en) | Crystalline abacavir hydrochloride monohydrate and process for its preparation | |
| CN119859139A (zh) | 双盐酸安罗替尼的固体形式及其制备方法 | |
| HK1209426B (en) | Process for the preparation of pemetrexed and lysin salt thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20220623 |
|
| EEER | Examination request |
Effective date: 20220623 |
|
| EEER | Examination request |
Effective date: 20220623 |
|
| EEER | Examination request |
Effective date: 20220623 |
|
| EEER | Examination request |
Effective date: 20220623 |
|
| EEER | Examination request |
Effective date: 20220623 |
|
| EEER | Examination request |
Effective date: 20220623 |