AR098128A1 - Proceso para la preparación de un inhibidor de pde4 - Google Patents
Proceso para la preparación de un inhibidor de pde4Info
- Publication number
- AR098128A1 AR098128A1 ARP140103938A ARP140103938A AR098128A1 AR 098128 A1 AR098128 A1 AR 098128A1 AR P140103938 A ARP140103938 A AR P140103938A AR P140103938 A ARP140103938 A AR P140103938A AR 098128 A1 AR098128 A1 AR 098128A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- indicated above
- meanings indicated
- compounds
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 5
- 238000002360 preparation method Methods 0.000 title abstract 3
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 23
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 abstract 2
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 abstract 2
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 abstract 2
- 230000003647 oxidation Effects 0.000 abstract 2
- 238000007254 oxidation reaction Methods 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 1
- 125000005199 aryl carbonyloxy group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000000969 carrier Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 238000013375 chromatographic separation Methods 0.000 abstract 1
- 238000004587 chromatography analysis Methods 0.000 abstract 1
- 238000002425 crystallisation Methods 0.000 abstract 1
- 230000008025 crystallization Effects 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 238000002955 isolation Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- -1 methanesulfonyl halide Chemical class 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 208000023504 respiratory system disease Diseases 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/61—Halogen atoms or nitro radicals
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- 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
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- 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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive 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
- A61P11/08—Bronchodilators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/10—Anti-acne agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
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- 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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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/59—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton the carbon skeleton being further substituted by singly-bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
- C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
-
- 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)
- 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Diabetes (AREA)
- Otolaryngology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Rheumatology (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Emergency Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Oncology (AREA)
- Neurosurgery (AREA)
- Vascular Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Proceso para la preparación de compuestos que poseen actividad inhibitoria de fosfodiesterasa (PDE4) de fórmula (1). También se relaciona con el proceso para el aislamiento por cristalización del compuesto de fórmula (1) y su uso para la preparación de composiciones farmacéuticas para inhalación en combinación con transportadores o vehículos adecuados. El producto sintetizado es adecuado para el uso en aplicaciones farmacéuticas por ejemplo en el tratamiento de enfermedades respiratorias. También reivindican los compuestos de fórmula (3), (4) y (5). Reivindicación 1: Un proceso para preparar un compuesto de fórmula (1) donde n es 0 ó 1, caracterizado porque dicho proceso comprende: a) hacer reaccionar un compuesto de fórmula (2) donde n es 0 ó 1, con un compuesto de fórmula (3) en donde X se selecciona entre -NHSO₂Me y -NO₂ y Z se selecciona entre -OH, cloro, bromo, C₁₋₆ alcoxilo lineal o ramificado, ariloxilo, arilalcoxilo, C₁₋₆ alquilcarboniloxilo, arilcarboniloxilo y aril-C₁₋₆ alquilcarboniloxilo para obtener un compuesto de fórmula (1) en donde n es 0 ó 1 o un compuesto de fórmula (4) en donde n tiene los significados indicados precedentemente y X es -NO₂; y, cuando un compuesto de fórmula (4) se obtiene en el paso a): b) reducirlo al compuesto correspondiente de fórmula (5) en donde n es 0 ó 1, y hacerlo reaccionar con halogenuro de metanosulfonilo para obtener un compuesto de fórmula (1) en donde n tiene los significados indicados precedentemente; y donde el compuesto de fórmula (2) en el paso a) se obtiene de acuerdo con cualquiera de los pasos alternativos c1) o c2) por: c1) oxidación de un compuesto de fórmula (6) en donde n es 0 ó 1 para obtener un compuesto de fórmula (7) en donde n es 0 ó 1, y posteriormente reducción enantioselectiva para obtener un compuesto de fórmula (2) en donde n tiene los significados indicados precedentemente; o c2) separación por cromatografía un compuesto de fórmula (6) en donde n es 0 ó 1, para obtener un compuesto de fórmula (2) y un compuesto de fórmula (8) en donde n tiene los significados indicados precedentemente; y opcionalmente oxidar el compuesto de fórmula (8) obtenido en el paso c2) al compuesto correspondiente de fórmula (7) para reducirlo posteriormente a un compuesto de fórmula (6) en donde n es 0 ó 1 y reprocesarlo en el proceso de separación cromatográfica; y en donde todos los compuestos de fórmula (1), (2), (4), (5), (6), (7) ú (8) en donde n es 1 pueden obtenerse por oxidación de los compuestos correspondientes en donde n es 0.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13189784 | 2013-10-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR098128A1 true AR098128A1 (es) | 2016-05-04 |
Family
ID=49385193
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP140103938A AR098128A1 (es) | 2013-10-22 | 2014-10-20 | Proceso para la preparación de un inhibidor de pde4 |
| ARP200100438A AR118124A2 (es) | 2013-10-22 | 2020-02-17 | Proceso para la preparación de un inhibidor de pde4 |
| ARP210101431A AR122183A2 (es) | 2013-10-22 | 2021-05-27 | Proceso para la preparación de una forma cristalina de un inhibidor de pde4, forma cristalina, composición farmacéutica para inhalación, usos y solvato |
| ARP210101430A AR122182A2 (es) | 2013-10-22 | 2021-05-27 | Procesos para la preparación de compuestos intermediarios de un inhibidor de pde4 y dichos compuestos intermediarios |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP200100438A AR118124A2 (es) | 2013-10-22 | 2020-02-17 | Proceso para la preparación de un inhibidor de pde4 |
| ARP210101431A AR122183A2 (es) | 2013-10-22 | 2021-05-27 | Proceso para la preparación de una forma cristalina de un inhibidor de pde4, forma cristalina, composición farmacéutica para inhalación, usos y solvato |
| ARP210101430A AR122182A2 (es) | 2013-10-22 | 2021-05-27 | Procesos para la preparación de compuestos intermediarios de un inhibidor de pde4 y dichos compuestos intermediarios |
Country Status (29)
| Country | Link |
|---|---|
| US (7) | US9434691B2 (es) |
| EP (5) | EP3293176B1 (es) |
| JP (5) | JP6458957B2 (es) |
| KR (3) | KR102287598B1 (es) |
| CN (5) | CN110256338A (es) |
| AR (4) | AR098128A1 (es) |
| AU (1) | AU2014339136C1 (es) |
| BR (1) | BR112016008161B1 (es) |
| CA (3) | CA3115570C (es) |
| CY (1) | CY1123811T1 (es) |
| DK (3) | DK3293176T3 (es) |
| ES (3) | ES2980505T3 (es) |
| FI (1) | FI3587400T3 (es) |
| HR (3) | HRP20240783T1 (es) |
| HU (3) | HUE046637T2 (es) |
| IL (4) | IL285528B2 (es) |
| LT (2) | LT3293176T (es) |
| MX (4) | MX389002B (es) |
| MY (1) | MY182559A (es) |
| PH (3) | PH12020500162B1 (es) |
| PL (3) | PL3293176T3 (es) |
| PT (3) | PT3060551T (es) |
| RS (2) | RS65452B1 (es) |
| RU (1) | RU2682660C9 (es) |
| SG (4) | SG10202112587RA (es) |
| SI (3) | SI3060551T1 (es) |
| TW (3) | TWI685486B (es) |
| UA (2) | UA127453C2 (es) |
| WO (1) | WO2015059050A1 (es) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI2600830T1 (en) | 2010-08-03 | 2018-05-31 | Chiesi Farmaceutici S.P.A. | Dry powder formulation comprising a phosphodiesterase inhibitor |
| JP6458957B2 (ja) | 2013-10-22 | 2019-01-30 | チエシ ファルマスティスィ エス．ピー．エー． | Ｐｄｅ４阻害剤の製造方法 |
| EP3487501A1 (en) * | 2016-07-20 | 2019-05-29 | Allergan, Inc. | Methods, compositions, and compounds for treatment of dermatological and ocular conditions |
| JP7361584B2 (ja) * | 2018-12-19 | 2023-10-16 | 高砂香料工業株式会社 | アミドの還元によるアミンの製造方法 |
| JP6780763B2 (ja) | 2018-12-25 | 2020-11-04 | トヨタ自動車株式会社 | 内燃機関の制御装置 |
| US11149615B2 (en) | 2018-12-25 | 2021-10-19 | Toyota Jidosha Kabushiki Kaisha | Control device for internal combustion engine |
| CN111808029A (zh) * | 2020-08-31 | 2020-10-23 | 兰晟生物医药(苏州)有限公司 | 一种pde4抑制剂氯比普兰的制备方法 |
| WO2023117985A1 (en) | 2021-12-21 | 2023-06-29 | Chiesi Farmaceutici S.P.A. | Dry powder formulations filled in an inhaler with improved resistance to humidity |
| JP2025514863A (ja) | 2022-04-27 | 2025-05-09 | キエシ・フアルマチエウテイチ・ソチエタ・ペル・アチオニ | Ｐｄｅ４阻害剤の新規結晶形態 |
| CN115304542B (zh) * | 2022-07-18 | 2024-02-02 | 湖南华纳大药厂手性药物有限公司 | 一种3-羟基吡啶的合成工艺 |
| WO2024027901A1 (en) | 2022-08-02 | 2024-02-08 | Chiesi Farmaceutici S.P.A. | Predictive biomarker of clinical response to a pde4 inhibitor |
| WO2024062006A1 (en) | 2022-09-22 | 2024-03-28 | Chiesi Farmaceutici S.P.A. | Capsule inhaler for the administration of a phosphodiesterase-4 inhibitor |
| CN119947705A (zh) | 2022-09-22 | 2025-05-06 | 奇斯药制品公司 | 用于施用磷酸二酯酶-4抑制剂的胶囊吸入器 |
| EP4590273A1 (en) | 2022-09-22 | 2025-07-30 | Chiesi Farmaceutici S.p.A. | Capsule inhaler for the administration of a phosphodiesterase-4 inhibitor |
| KR20250079386A (ko) | 2023-11-27 | 2025-06-04 | 국립한국해양대학교산학협력단 | 복수의 학습모델을 이용한 이미지 기반의 강도 추정 장치 및 방법 |
Family Cites Families (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5935978A (en) * | 1991-01-28 | 1999-08-10 | Rhone-Poulenc Rorer Limited | Compounds containing phenyl linked to aryl or heteroaryl by an aliphatic- or heteroatom-containing linking group |
| CA2414049A1 (en) * | 2000-03-30 | 2001-10-11 | Chirotech Technology Limited | Ruthenium-diphosphine complexes and their use as catalysts |
| EP1670742A1 (en) * | 2003-09-12 | 2006-06-21 | Ranbaxy Laboratories Limited | Process for the preparation of roflumilast |
| ES2577303T3 (es) | 2004-04-19 | 2016-07-14 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Procedimientos para la preparación de la forma polimórfica I de hidrogenosulfato de clopidogrel |
| DK1749001T3 (da) * | 2004-04-29 | 2010-06-28 | Aventis Pharma Inc | 3-piperidinylisochroman-5-ol som dopaminagonister |
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