PT108370B - Processo de preparação de brometo de aclidínio - Google Patents
Processo de preparação de brometo de aclidínio Download PDFInfo
- Publication number
- PT108370B PT108370B PT10837015A PT10837015A PT108370B PT 108370 B PT108370 B PT 108370B PT 10837015 A PT10837015 A PT 10837015A PT 10837015 A PT10837015 A PT 10837015A PT 108370 B PT108370 B PT 108370B
- Authority
- PT
- Portugal
- Prior art keywords
- bromide
- solvent
- process according
- mixture
- aclidinium
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- JUGRTVJQTFZHOM-UHFFFAOYSA-N 1,1,1-tribromo-2-methylpropan-2-ol Chemical compound CC(C)(O)C(Br)(Br)Br JUGRTVJQTFZHOM-UHFFFAOYSA-N 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 45
- ASMXXROZKSBQIH-VITNCHFBSA-N aclidinium Chemical class 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 claims abstract description 31
- 229960005012 aclidinium bromide Drugs 0.000 claims abstract description 24
- 239000000725 suspension Substances 0.000 claims abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 239000002904 solvent Substances 0.000 claims description 41
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 37
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 26
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 21
- 239000000047 product Substances 0.000 claims description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 239000000243 solution Substances 0.000 claims description 12
- 239000000843 powder Substances 0.000 claims description 11
- 239000011877 solvent mixture Substances 0.000 claims description 11
- 238000001035 drying Methods 0.000 claims description 10
- -1 3-phenoxypropyl Chemical group 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 8
- GUTQMBQKTSGBPQ-UHFFFAOYSA-N dithiophen-2-ylmethanone Chemical group C=1C=CSC=1C(=O)C1=CC=CS1 GUTQMBQKTSGBPQ-UHFFFAOYSA-N 0.000 claims description 8
- NIDWUZTTXGJFNN-UHFFFAOYSA-N 3-bromopropoxybenzene Chemical compound BrCCCOC1=CC=CC=C1 NIDWUZTTXGJFNN-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- 239000011261 inert gas Substances 0.000 claims description 4
- 239000008101 lactose Substances 0.000 claims description 4
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 238000000746 purification Methods 0.000 claims description 4
- 125000003375 sulfoxide group Chemical group 0.000 claims description 4
- 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 claims description 3
- 229940019903 aclidinium Drugs 0.000 claims description 3
- 238000001694 spray drying Methods 0.000 claims description 3
- 150000003462 sulfoxides Chemical class 0.000 claims description 3
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 238000000113 differential scanning calorimetry Methods 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 239000012264 purified product Substances 0.000 claims description 2
- 238000001757 thermogravimetry curve Methods 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 238000002411 thermogravimetry Methods 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 230000001684 chronic effect Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000001307 helium Substances 0.000 claims 1
- 229910052734 helium Inorganic materials 0.000 claims 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 claims 1
- 229910052741 iridium Inorganic materials 0.000 claims 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims 1
- 238000000634 powder X-ray diffraction Methods 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 229930195727 α-lactose Natural products 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 239000002245 particle Substances 0.000 description 10
- 238000004128 high performance liquid chromatography Methods 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000004626 scanning electron microscopy Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000009826 distribution Methods 0.000 description 4
- 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 description 4
- 238000005956 quaternization reaction Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229960001375 lactose Drugs 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000005809 transesterification reaction Methods 0.000 description 3
- 230000007704 transition Effects 0.000 description 3
- 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 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 231100000024 genotoxic Toxicity 0.000 description 2
- 230000001738 genotoxic effect Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000000463 material 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
- 239000007858 starting material Substances 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 101100532856 Arabidopsis thaliana SDRA gene Proteins 0.000 description 1
- 101150049479 CCNC gene Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 1
- 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 1
- 241001442234 Cosa Species 0.000 description 1
- 244000182067 Fraxinus ornus Species 0.000 description 1
- 101100469010 Homo sapiens RIOX2 gene Proteins 0.000 description 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 208000011623 Obstructive Lung disease Diseases 0.000 description 1
- 101000608752 Phytolacca americana Lectin-C Proteins 0.000 description 1
- 241000183024 Populus tremula Species 0.000 description 1
- NFQIAEMCQGTTIR-UHFFFAOYSA-N Repirinast Chemical compound C12=CC=C(C)C(C)=C2NC(=O)C2=C1OC(C(=O)OCCC(C)C)=CC2=O NFQIAEMCQGTTIR-UHFFFAOYSA-N 0.000 description 1
- 102100022092 Ribosomal oxygenase 2 Human genes 0.000 description 1
- YPALLBOSSJZATK-UHFFFAOYSA-N [He].Br Chemical compound [He].Br YPALLBOSSJZATK-UHFFFAOYSA-N 0.000 description 1
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 238000005085 air analysis Methods 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000013480 data collection Methods 0.000 description 1
- 238000001938 differential scanning calorimetry curve Methods 0.000 description 1
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
- 235000019797 dipotassium phosphate Nutrition 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 150000004694 iodide salts Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229960001021 lactose monohydrate Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 230000000877 morphologic effect Effects 0.000 description 1
- 239000003149 muscarinic antagonist Substances 0.000 description 1
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- OCYSGIYOVXAGKQ-FVGYRXGTSA-N phenylephrine hydrochloride Chemical compound [H+].[Cl-].CNC[C@H](O)C1=CC=CC(O)=C1 OCYSGIYOVXAGKQ-FVGYRXGTSA-N 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 229950009147 repirinast Drugs 0.000 description 1
- 238000005185 salting out Methods 0.000 description 1
- 238000001878 scanning electron micrograph Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- FIAFUQMPZJWCLV-UHFFFAOYSA-N suramin Chemical compound OS(=O)(=O)C1=CC(S(O)(=O)=O)=C2C(NC(=O)C3=CC=C(C(=C3)NC(=O)C=3C=C(NC(=O)NC=4C=C(C=CC=4)C(=O)NC=4C(=CC=C(C=4)C(=O)NC=4C5=C(C=C(C=C5C(=CC=4)S(O)(=O)=O)S(O)(=O)=O)S(O)(=O)=O)C)C=CC=3)C)=CC=C(S(O)(=O)=O)C2=C1 FIAFUQMPZJWCLV-UHFFFAOYSA-N 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical group [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Otolaryngology (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
- Catalysts (AREA)
Priority Applications (14)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PT10837015A PT108370B (pt) | 2015-03-30 | 2015-03-30 | Processo de preparação de brometo de aclidínio |
| PCT/GB2016/050888 WO2016156836A1 (en) | 2015-03-30 | 2016-03-30 | Process for the preparation of aclidinium bromide |
| CN201680031574.2A CN108112252B (zh) | 2015-03-30 | 2016-03-30 | 制备阿地溴铵的方法 |
| AU2016240289A AU2016240289B2 (en) | 2015-03-30 | 2016-03-30 | Process for the preparation of aclidinium bromide |
| US15/562,814 US10087177B2 (en) | 2015-03-30 | 2016-03-30 | Process for the preparation of aclidinium bromide |
| JP2017551330A JP2018510189A (ja) | 2015-03-30 | 2016-03-30 | アクリジニウム臭化物の製造方法 |
| CA2980665A CA2980665A1 (en) | 2015-03-30 | 2016-03-30 | Process for the preparation of aclidinium bromide |
| EP16717989.4A EP3277679A1 (en) | 2015-03-30 | 2016-03-30 | Process for the preparation of aclidinium bromide |
| CA3165243A CA3165243A1 (en) | 2015-03-30 | 2016-03-30 | Crystalline aclidinium bromide and uses thereof |
| IL254712A IL254712A0 (en) | 2015-03-30 | 2017-09-26 | A process for the preparation of aclidinium bromide |
| US16/114,714 US10590124B2 (en) | 2015-03-30 | 2018-08-28 | Process for the preparation of aclidinium bromide |
| JP2020097781A JP2020143160A (ja) | 2015-03-30 | 2020-06-04 | アクリジニウム臭化物の製造方法 |
| JP2020185042A JP7124035B2 (ja) | 2015-03-30 | 2020-11-05 | アクリジニウム臭化物の製造方法 |
| JP2022128244A JP2022160667A (ja) | 2015-03-30 | 2022-08-10 | アクリジニウム臭化物の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PT10837015A PT108370B (pt) | 2015-03-30 | 2015-03-30 | Processo de preparação de brometo de aclidínio |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PT108370A PT108370A (pt) | 2016-09-30 |
| PT108370B true PT108370B (pt) | 2018-10-25 |
Family
ID=55806548
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT10837015A PT108370B (pt) | 2015-03-30 | 2015-03-30 | Processo de preparação de brometo de aclidínio |
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) | CA3165243A1 (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. |
| AU2930501A (en) * | 2000-01-07 | 2001-07-24 | 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. |
| JP2007500151A (ja) * | 2003-07-29 | 2007-01-11 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ベータ受容体刺激薬及び抗コリン薬を含む吸入用医薬 |
| 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. |
| EP3401316B1 (en) * | 2012-08-15 | 2021-08-04 | 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 CA CA3165243A patent/CA3165243A1/en active Pending
- 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 AU AU2016240289A patent/AU2016240289B2/en not_active Ceased
- 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 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 |
|---|---|
| US20180105517A1 (en) | 2018-04-19 |
| US10087177B2 (en) | 2018-10-02 |
| AU2016240289B2 (en) | 2020-08-27 |
| JP2020143160A (ja) | 2020-09-10 |
| US10590124B2 (en) | 2020-03-17 |
| IL254712A0 (en) | 2017-11-30 |
| CN108112252A (zh) | 2018-06-01 |
| AU2016240289A1 (en) | 2017-10-19 |
| PT108370A (pt) | 2016-09-30 |
| JP7124035B2 (ja) | 2022-08-23 |
| EP3277679A1 (en) | 2018-02-07 |
| CA2980665A1 (en) | 2016-10-06 |
| US20180362523A1 (en) | 2018-12-20 |
| JP2021020965A (ja) | 2021-02-18 |
| JP2022160667A (ja) | 2022-10-19 |
| JP2018510189A (ja) | 2018-04-12 |
| CA3165243A1 (en) | 2016-10-06 |
| WO2016156836A1 (en) | 2016-10-06 |
| CN108112252B (zh) | 2020-11-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| PT108370B (pt) | Processo de preparação de brometo de aclidínio | |
| JP5337261B2 (ja) | 縮合複素環誘導体の塩及びその結晶 | |
| AU2015330554B2 (en) | Crystal form of bisulfate of JAK inhibitor and preparation method therefor | |
| CN114761381B (zh) | 7h-苯并[7]轮烯-2-甲酸衍生物的结晶形式 | |
| BR112014019736B1 (pt) | Processo para preparar brometo de tiotrópio | |
| ES2607890T3 (es) | Proceso para la preparación de pemetrexed y de sal de lisina del mismo | |
| WO2012077138A1 (en) | Methods of crystallizing (r) -1- (3 -hydroxypropyl) -5- [2- [2- [2- ( 2, 2, 2 - trifluoroethoxy) phenoxy] ethylamino] propyl] indoline-7 -carboxamide | |
| EP3256474A1 (en) | Ibrutinib sulphate salt | |
| JP2018511646A (ja) | 多形体及びキナゾリニル誘導体の調製プロセス | |
| ES2214318T5 (es) | Cristales de mirtazapina anhidra y procedimiento para su produccion. | |
| WO2011007870A1 (ja) | ２－［［［２－［（ヒドロキシアセチル）アミノ］－４－ピリジニル］メチル］チオ］－ｎ－［４－（トリフルオロメトキシ）フェニル］－３－ピリジンカルボキサミドのベンゼンスルホン酸塩、その結晶、その結晶多形およびそれらの製造方法 | |
| CN102428098B (zh) | {[(2s，5r，8s，11s)-5-苄基-11-(3-胍基-丙基)-8-异丙基-7-甲基-3，6，9，12，15-五氧代-1，4，7，10，13-五氮杂-环十五烷-2-基]-乙酸}的新固体物质和获得它们的方法 | |
| CN104876841B (zh) | 晶体态盐酸沃尼妙林产品及其结晶制备方法 | |
| CN110461844B (zh) | 5-甲基-(6s)-四氢叶酸与有机碱的结晶二元钠盐 | |
| US8604208B2 (en) | Polymorphs of sorafenib acid addition salts | |
| KR101589910B1 (ko) | 결정형 α 탈티레린의 제조방법 및 결정형의 변환방법 | |
| ES2557893T3 (es) | Sal de tosilato de 4-(6-cloro-3-metil-4,10-dihidro-3H-2,3,4,9-tetrabenzo[f]azuleno-9-carbonil)-2-fluorobencilamida del ácido ciclopropanocarboxílico | |
| US9834540B2 (en) | Omeprazole Sodium semihydrate and preparation method thereof | |
| CZ33762U1 (cs) | Pevné formy selektivního JAK-1 inhibitoru | |
| JP2016523899A (ja) | ゲフィチニブの新規な結晶形およびその製造方法 | |
| WO2023187762A1 (en) | Co-crystals of vortioxetine hydrobromide | |
| TW201720818A (zh) | 哌嗪化合物的新穎結晶 | |
| US20090018346A1 (en) | Amorphous Form Of Darifenacin Hydrobromide And Processes For The Preparation Thereof | |
| CN106432253A (zh) | 一种维帕他韦新晶型及其制备方法 | |
| ES2651854T3 (es) | Clorhidrato de abacavir monohidrato cristalino y procedimiento para su preparación |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BB1A | Laying open of patent application |
Effective date: 20160708 |
|
| FG3A | Patent granted, date of granting |
Effective date: 20181022 |