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PE20120055A1 - (1-fenil-2-piridin-4-il)etil esteres del acido benzoico como inhibidores de fosfodiesterasa - Google Patents

(1-fenil-2-piridin-4-il)etil esteres del acido benzoico como inhibidores de fosfodiesterasa

Info

Publication number
PE20120055A1
PE20120055A1 PE2011001441A PE2011001441A PE20120055A1 PE 20120055 A1 PE20120055 A1 PE 20120055A1 PE 2011001441 A PE2011001441 A PE 2011001441A PE 2011001441 A PE2011001441 A PE 2011001441A PE 20120055 A1 PE20120055 A1 PE 20120055A1
Authority
PE
Peru
Prior art keywords
pyridin
phenyl
cyclopropylmetoxy
halogen
benzoic acid
Prior art date
Application number
PE2011001441A
Other languages
English (en)
Inventor
Gabriele Amari
Elisabetta Armani
Maurizio Delcanale
Original Assignee
Chiesi Farma Spa
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=40674203&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=PE20120055(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Chiesi Farma Spa filed Critical Chiesi Farma Spa
Publication of PE20120055A1 publication Critical patent/PE20120055A1/es

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61MDEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M15/00Inhalators
    • A61M15/0065Inhalators with dosage or measuring devices
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/44Non condensed pyridines; Hydrogenated derivatives thereof
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/47Quinolines; Isoquinolines
    • A61K31/47042-Quinolinones, e.g. carbostyril
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K45/00Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
    • A61K45/06Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61MDEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M16/00Devices for influencing the respiratory system of patients by gas treatment, e.g. ventilators; Tracheal tubes
    • A61M16/10Preparation of respiratory gases or vapours
    • A61M16/14Preparation of respiratory gases or vapours by mixing different fluids, one of them being in a liquid phase
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/02Nasal agents, e.g. decongestants
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00Drugs for disorders of the respiratory system
    • A61P11/06Antiasthmatics
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00Drugs for dermatological disorders
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/08Antiallergic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/24Heterocyclic 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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/04Heterocyclic 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
    • C07D213/60Heterocyclic 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
    • C07D213/61Halogen atoms or nitro radicals
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D213/00Heterocyclic 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
    • C07D213/02Heterocyclic 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
    • C07D213/89Heterocyclic 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

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Pulmonology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Epidemiology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Biomedical Technology (AREA)
  • Hematology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Anesthesiology (AREA)
  • Biophysics (AREA)
  • Emergency Medicine (AREA)
  • Dermatology (AREA)
  • Otolaryngology (AREA)
  • Immunology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Enzymes And Modification Thereof (AREA)

Abstract

SE REFIERE A COMPUESTOS DERIVADOS DE (1-FENIL-2-PIRIDIN-4-IL)ETIL ESTERES DEL ACIDO BENZOICO DE FORMULA (I) COMO (-) ENANTIOMERO DONDE n ES 0 O 1; R1 Y R2 SON CADA UNO ALQUILO(C1-C6) OPCIONALMENTE SUSTITUIDO CON HALOGENO, OR3 O HNSO2R4, EN DONDE R3 ES ALQUILO(C1-C6) OPCIONALMENTE SUSTITUIDO CON HALOGENO O CICLOALQUILO(C3-C7); R4 ES ALQUILO(C1-C4) OPCIONALMENTE SUSTITUIDO CON HALOGENO. SON COMPUESTOS PREFERIDOS: 1-(S)-(3-CICLOPROPILMETOXI-4-DIFLUOROMETOXI-FENIL)-2-(3,5-DICLORO-PIRIDIN-4-IL)-ETIL ESTER DEL ACIDO 3-CICLOPROPILMETOXI-4-METANOSULFONILAMINO-BENZOICO; 1-(S)-(3-CICLOPROPILMETOXI-4-DIFLUOROMETOXI-FENIL)-2-(3,5-DICLORO-1-OXI-PIRIDIN-4-IL)-ETIL ESTER DEL ACIDO 3-CICLOPROPILMETOXI-4-METANOSULFONILAMINO-BENZOICO; ENTRE OTROS. TAMBIEN SE REFIERE A UN PROCESO DE PREPARACION Y A UNA COMPOSICION FARMACEUTICA QUE ADEMAS CONTIENE FORMOTEROL O CARMOTEROL. DICHOS COMPUESTOS SON INHIBIDORES DE LA ENZIMA FOSFODIESTERASA 4 (PDE4) SIENDO UTILES EN EL TRATAMIENTO DE ASMA, ENFERMEDAD PULMONAR OBSTRUCTIVA CRONICA
PE2011001441A 2009-02-06 2010-02-04 (1-fenil-2-piridin-4-il)etil esteres del acido benzoico como inhibidores de fosfodiesterasa PE20120055A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
EP09001660A EP2216327A1 (en) 2009-02-06 2009-02-06 Benzoic acid (1-phenyl-2-pyridin-4-yl)ethyl esters as phosphodiesterase inhibitors

Publications (1)

Publication Number Publication Date
PE20120055A1 true PE20120055A1 (es) 2012-02-16

Family

ID=40674203

Family Applications (1)

Application Number Title Priority Date Filing Date
PE2011001441A PE20120055A1 (es) 2009-02-06 2010-02-04 (1-fenil-2-piridin-4-il)etil esteres del acido benzoico como inhibidores de fosfodiesterasa

Country Status (33)

Country Link
US (5) US8440834B2 (es)
EP (2) EP2216327A1 (es)
JP (2) JP5612610B2 (es)
KR (1) KR101337728B1 (es)
CN (1) CN102317262B (es)
AR (1) AR075243A1 (es)
AU (1) AU2010211274B2 (es)
BR (1) BRPI1005695A8 (es)
CA (1) CA2751494C (es)
CL (1) CL2011001876A1 (es)
CO (1) CO6400217A2 (es)
CY (1) CY1113764T1 (es)
EA (1) EA019113B1 (es)
ES (1) ES2395528T3 (es)
GE (1) GEP20135919B (es)
HR (1) HRP20121004T1 (es)
IL (1) IL214446A (es)
JO (1) JO2761B1 (es)
MA (1) MA33105B1 (es)
ME (1) ME02325B (es)
MX (1) MX2011007857A (es)
MY (1) MY152048A (es)
NZ (1) NZ594413A (es)
PE (1) PE20120055A1 (es)
PL (1) PL2393782T3 (es)
PT (1) PT2393782E (es)
RS (1) RS52605B (es)
SG (1) SG173208A1 (es)
SI (1) SI2393782T1 (es)
TN (1) TN2011000346A1 (es)
TW (1) TWI459945B (es)
UA (1) UA102574C2 (es)
WO (1) WO2010089107A1 (es)

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EP2022783A1 (en) * 2007-08-08 2009-02-11 CHIESI FARMACEUTICI S.p.A. "Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors"
EP2216327A1 (en) * 2009-02-06 2010-08-11 CHIESI FARMACEUTICI S.p.A. Benzoic acid (1-phenyl-2-pyridin-4-yl)ethyl esters as phosphodiesterase inhibitors
CA2807406C (en) 2010-08-03 2018-12-11 Chiesi Farmaceutici S.P.A. Pharmaceutical formulation comprising a phosphodiesterase inhibitor
SI2600830T1 (en) * 2010-08-03 2018-05-31 Chiesi Farmaceutici S.P.A. Dry powder formulation comprising a phosphodiesterase inhibitor
EP2718267B1 (en) 2011-06-06 2016-08-10 Chiesi Farmaceutici S.p.A. Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors
EP2760838B1 (en) 2011-09-26 2017-05-10 Chiesi Farmaceutici S.p.A. Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors
CN103889972A (zh) * 2011-10-21 2014-06-25 奇斯药制品公司 作为磷酸二酯酶抑制剂的1-苯基-2-吡啶基烷基醇的衍生物
AR089232A1 (es) * 2011-12-16 2014-08-06 Chiesi Farma Spa Potenciacion inducida por inhibidores de pde4 en el tratamiento de la leucemia
IN2014DN10239A (es) 2012-06-04 2015-08-07 Chiesi Farma Spa
AR093796A1 (es) * 2012-12-05 2015-06-24 Chiesi Farm Spa Derivados del alcohol 1-fenil-2-piridinil alquilico como inhibidores de la fosfodiesterasa
KR20150091061A (ko) 2012-12-05 2015-08-07 키에시 파르마슈티시 엣스. 피. 에이. Pde4-억제제로서 페닐에틸피리딘 유도체
HK1212988A1 (zh) 2012-12-05 2016-07-22 奇斯药制品公司 作为pde-4抑制剂的苯基乙基吡啶衍生物
WO2014086852A1 (en) 2012-12-05 2014-06-12 Chiesi Farmaceutici S.P.A. Phenylethylpyridine derivatives as pde4-inhibitors
US9427376B2 (en) 2013-10-10 2016-08-30 Chiesi Farmaceutici S.P.A. Process for preparing pharmaceutical formulations for inhalation comprising a high-dosage strength active ingredient
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
AR098621A1 (es) 2013-12-05 2016-06-01 Chiesi Farm Spa Derivados de heteroarilo
HK1225384A1 (zh) 2013-12-05 2017-09-08 奇斯药制品公司 用於治疗呼吸病的二苯甲基衍生物
EP3152202B1 (en) * 2014-06-04 2018-11-28 Chiesi Farmaceutici S.p.A. 3,5-dichloro,4-(3,4-(cyclo-)alkoxyphenyl)--2-carbonyloxy)ethyl)pyridine derivatives as pde-4 inhibitors and muscarinic m3 receptor antagonists
EP3152203A1 (en) * 2014-06-04 2017-04-12 Chiesi Farmaceutici S.p.A. 3,5-dichloro,4-(3,4-(cyclo-)alkoxyphenyl)- 2-carbonyloxy)ethyl)pyridine derivatives as pde-4 inhibitors
US9326976B2 (en) 2014-06-05 2016-05-03 Chiesi Farmaceutici S.P.A. Carbamate derivatives
US9763924B2 (en) * 2014-06-05 2017-09-19 Chiesi Farmaceutici S.P.A. Aminoester derivatives
WO2017089347A1 (en) 2015-11-25 2017-06-01 Inserm (Institut National De La Sante Et De La Recherche Medicale) Methods and pharmaceutical compositions for the treatment of braf inhibitor resistant melanomas
EP3487501A1 (en) * 2016-07-20 2019-05-29 Allergan, Inc. Methods, compositions, and compounds for treatment of dermatological and ocular conditions
MA51413A (fr) * 2017-12-28 2021-04-28 Chiesi Farm Spa Utilisation de dérivés d'alcool alkylique de 1-phényl-2-pyridinyl pour le traitement de la fibrose kystique
US11813360B2 (en) 2018-07-27 2023-11-14 Chiesi Farmaceutici S.P.A. Carrier particles for dry powder formulations for inhalation
CN115466169B (zh) * 2021-06-10 2024-03-26 中国医学科学院药物研究所 取代邻苯二酚醚类化合物及其制备方法和应用
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
WO2024027901A1 (en) 2022-08-02 2024-02-08 Chiesi Farmaceutici S.P.A. Predictive biomarker of clinical response to a pde4 inhibitor
EP4590273A1 (en) 2022-09-22 2025-07-30 Chiesi Farmaceutici S.p.A. Capsule inhaler for the administration of a phosphodiesterase-4 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
GB202306663D0 (en) 2023-05-05 2023-06-21 Union Therapeutics As Combination therapy

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PL178314B1 (pl) 1993-07-02 2000-04-28 Byk Gulden Lomberg Chem Fab Benzamidy podstawione grupą fluoroalkoksylową, hamujące fosfodiesterazę cyklicznych nukleotydów, sposób ich otrzymywania i lek zawierający podstawione benzamidy
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EP2022783A1 (en) 2007-08-08 2009-02-11 CHIESI FARMACEUTICI S.p.A. "Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors"
EP2070913A1 (en) 2007-12-14 2009-06-17 CHIESI FARMACEUTICI S.p.A. Ester derivatives as phosphodiesterase inhibitors
EP2110375A1 (en) 2008-04-14 2009-10-21 CHIESI FARMACEUTICI S.p.A. Phosphodiesterase-4 inhibitors belonging to the tertiary amine class
EP2216327A1 (en) * 2009-02-06 2010-08-11 CHIESI FARMACEUTICI S.p.A. Benzoic acid (1-phenyl-2-pyridin-4-yl)ethyl esters as phosphodiesterase inhibitors
SI2600830T1 (en) 2010-08-03 2018-05-31 Chiesi Farmaceutici S.P.A. Dry powder formulation comprising a phosphodiesterase inhibitor
CA2807406C (en) 2010-08-03 2018-12-11 Chiesi Farmaceutici S.P.A. Pharmaceutical formulation comprising a phosphodiesterase inhibitor
EP2718267B1 (en) 2011-06-06 2016-08-10 Chiesi Farmaceutici S.p.A. Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors
EP2760838B1 (en) 2011-09-26 2017-05-10 Chiesi Farmaceutici S.p.A. Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors
CN103889972A (zh) 2011-10-21 2014-06-25 奇斯药制品公司 作为磷酸二酯酶抑制剂的1-苯基-2-吡啶基烷基醇的衍生物
IN2014DN10239A (es) 2012-06-04 2015-08-07 Chiesi Farma Spa
AR093796A1 (es) 2012-12-05 2015-06-24 Chiesi Farm Spa Derivados del alcohol 1-fenil-2-piridinil alquilico como inhibidores de la fosfodiesterasa

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BRPI1005695A2 (pt) 2017-06-06
HK1162508A1 (en) 2012-08-31
CO6400217A2 (es) 2012-03-15
HRP20121004T1 (hr) 2012-12-31
JP2012516863A (ja) 2012-07-26
US8440834B2 (en) 2013-05-14
CL2011001876A1 (es) 2011-10-28
US20130012487A1 (en) 2013-01-10
MA33105B1 (fr) 2012-03-01
EP2216327A1 (en) 2010-08-11
AR075243A1 (es) 2011-03-16
AU2010211274B2 (en) 2016-03-17
UA102574C2 (ru) 2013-07-25
PL2393782T3 (pl) 2013-02-28
US20140179647A1 (en) 2014-06-26
CN102317262A (zh) 2012-01-11
RS52605B (sr) 2013-04-30
WO2010089107A1 (en) 2010-08-12
PT2393782E (pt) 2012-12-26
US9056176B2 (en) 2015-06-16
AU2010211274A1 (en) 2011-08-25
CY1113764T1 (el) 2016-07-27
IL214446A0 (en) 2011-09-27
JP5612610B2 (ja) 2014-10-22
KR101337728B1 (ko) 2013-12-09
EA019113B1 (ru) 2014-01-30
EA201190099A1 (ru) 2012-02-28
TWI459945B (zh) 2014-11-11
TN2011000346A1 (en) 2013-03-27
EP2393782A1 (en) 2011-12-14
JP2015038079A (ja) 2015-02-26
EP2393782B1 (en) 2012-09-12
JO2761B1 (en) 2014-03-15
NZ594413A (en) 2013-05-31
MY152048A (en) 2014-08-15
CA2751494A1 (en) 2010-08-12
US20100204256A1 (en) 2010-08-12
ME02325B (me) 2016-06-20
US20130289010A1 (en) 2013-10-31
KR20110094356A (ko) 2011-08-23
MX2011007857A (es) 2011-08-15
US8648204B2 (en) 2014-02-11
ES2395528T3 (es) 2013-02-13
SG173208A1 (en) 2011-09-29
SI2393782T1 (sl) 2013-01-31
US20140378423A1 (en) 2014-12-25
IL214446A (en) 2014-12-31
CN102317262B (zh) 2014-08-06
GEP20135919B (en) 2013-09-10
CA2751494C (en) 2017-03-07
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TW201032804A (en) 2010-09-16
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