SI2947068T1 - Derivati 1-fenil-2-piridinil alkil alkoholov kot inhibitorji fosfodiesteraze - Google Patents

Derivati 1-fenil-2-piridinil alkil alkoholov kot inhibitorji fosfodiesteraze Download PDF

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SI2947068T1
SI2947068T1 SI200831909T SI200831909T SI2947068T1 SI 2947068 T1 SI2947068 T1 SI 2947068T1 SI 200831909 T SI200831909 T SI 200831909T SI 200831909 T SI200831909 T SI 200831909T SI 2947068 T1 SI2947068 T1 SI 2947068T1
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Prior art keywords
optionally substituted
alkyl
halogen atoms
phenyl
branched
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SI200831909T
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English (en)
Inventor
Maurizio Delcanale
Gabriele Amari
Elisabetta Armani
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Chiesi Farmaceutici S.P.A.
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Publication of SI2947068T1 publication Critical patent/SI2947068T1/sl

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    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
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    • 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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    • 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
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4433—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with oxygen as a ring hetero atom
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
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    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A61K31/4523—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems
    • A61K31/4545—Non condensed piperidines, e.g. piperocaine containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/455—Nicotinic acids, e.g. niacin; Derivatives thereof, e.g. esters, amides
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    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • A61K31/52—Purines, e.g. adenine
    • A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
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    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
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    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/538—1,4-Oxazines, e.g. morpholine ortho- or peri-condensed with carbocyclic ring systems
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    • 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
    • C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
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    • 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
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Claims (11)

  1. EP 2947068 DERIVATI 1-FENIL-2-PIRIDINIL ALKIL ALKOHOLOV KOT INHIBITORJI FOSFODIESTERAZE PATENTNI ZAHTEVKI
    1. Formulacija praška, ki jo je mogoče inhalirati, obsegajoča spojino s splošno formulo (II)
    kjer Z je izbran iz skupine, ki jo sestavljajo (CH2)m, kjer m = 0, 1 ali 2; in CR4R5, kjer R4 je neodvisno izbran iz H ali linearnega ali razvejanega (C1-C4) alkila, opcijsko substituiranega z enim ali več atomi halogena ali s (C1-C4) cikloalkilom in R5 je neodvisno izbran iz skupine, ki jo sestavljajo - linearen ali razvejan (C1-C4) alkil, opcijsko substituiran z enim ali več atomi halogena; - fenil; - benzil; - NH2; in - HNCOOR’, kjer je R’ linearen ali razvejan (C1-C4) alkil, opcijsko substituiran z enim ali več atomi halogena; R1 in R2 sta različna ali enaka in sta neodvisno izbrana iz skupine, ki jo sestavljajo -H; - linearen ali razvejan (Ci-Ce) alkil, opcijsko substituiran z enim ali več substituenti, izbranimi iz atomov halogena, (C3-C7) cikloalkila ali (C5-C7) cikloalkenila; - (C3-C7) cikloalkil; - (C5-C7) cikloalkenil; - linearen ali razvejan (C2-C6) alkenil; in - linearen ali razvejan (C2-Ce) alkinil; A je fenil, opcijsko substituiran z eno ali več skupinami Rx, ali je A heteroarilni obroč, opcijsko substituiran z eno ali več skupinami Rx, kjer je A heteroarilni obroč, izbran iz skupine, ki jo sestavljajo pirol, pirazol, furan, tiofen, imidazol, oksazol, izoksazol, tiazol, piridin, pirimidin, pirazin, piridazin in piran, pri katerih je opcijski substituent Rx na obročnem sistemu A lahko eden ali jih je več, je lahko enak ali različen, in je neodvisno izbran iz skupine, ki jo sestavljajo: - linearen ali razvejan (Ci-C6) alkil, opcijsko substituiran z enim ali več atomi halogena ali (C3-C7) cikloalkilom; - linearen ali razvejan (C2-C6) alkenil, opcijsko substituiran z enim ali več (C3-C7) cikloalkili; - linearen ali razvejan (C2-C6) alkinil, opcijsko substituiran z enim ali več (C3-C7) cikloalkili; - (C5-C7) cikloalkenil; - fenil; - (C3-C7) heterocikloalkil; - OR7, kjer je R7 izbran iz skupine, ki jo sestavljajo -H; - (C1-C10) alkil, opcijsko substituiran z enim ali več atomi halogena ali (C3-C7) cikloalkilom; - (C3-C7) cikloalkil; - (C1-C4) alkilen-(C3-C7) heterocikloalkil; - CCHCrCe) alkil, kjer je (C1-C6) alkil opcijsko substituiran z enim ali več atomi halogena; - COO-(Ci-Ce) alkil, kjer je (C1-C6) alkil opcijsko substituiran z enim ali več atomi halogena; - fenil; - benzil; - (C1-C10) alkil-NRsRg, kjer sta Re in Rg neodvisno izbrana iz skupine, ki jo sestavljajo H, linearen ali razvejan (Ci-C6) alkil, opcijsko substituiran z enim ali več atomi halogena, in tvorita z atomom dušika, na katerega sta vezana, nasičen, deloma nasičen ali nenasičen obroč; in - atomi halogena; -CN; -N02; - NR10R11, kjer sta R10 in Rn različna ali enaka in sta neodvisno izbrana iz skupine, ki jo sestavljajo -H; - linearen ali razvejan (Ci-C6) alkil, opcijsko substituiran z enim ali več atomi halogena, fenilom ali (C3-C7) cikloalkilom; - COC6H5; - C0-(CrC4) alkil, kjer je (C1-C4) alkil opcijsko substituiran z enim ali več atomi halogena; - COO-(Ci-C4) alkil, kjer je (C1-C4) alkil opcijsko substituiran z enim ali več atomi halogena; - CONH-(Ci-C6) alkil-Ri2, kjer je R12 izbran iz skupine, ki jo sestavljajo -H; - (C1-C4) alkil, opcijsko substituiran z enim ali več atomi halogena; - OR4R5; in - CONH (C1-C4) alkil-N(Ci-C4) alkil, kjer je N(CrC4) alkil opcijsko substituiran z enim ali več atomi halogena; ali tvorijo z atomom dušika, na katerega so vezani, nasičen ali deloma nasičen obroč; -(C1-C4) alkil-NR10Rn; - COR12, kjer je R12 fenil ali linearen ali razvejan (C1-C6) alkil, opcijsko substituiran z enim ali več atomi halogena; - okso; - HNSO2R13, kjer je R13 (C1-C4) alkil, opcijsko substituiran z enim ali več atomi halogena ali fenil, opcijsko substituiran z atomi halogena ali s (C1-C4) alkilno skupino, opcijsko substituirano z enim ali več atomi halogena; - SO2R14, kjer je R14 (C1-C4) alkil, opcijsko substituiran z enim ali več atomi halogena, OH ali NR10R11, kjer sta R10 in Rn, kot je definirano zgoraj; - SOR15, kjer je R15 fenil ali (CrC4) alkil, opcijsko substituiran z enim ali več atomi halogena; - SR16, kjer je R16 H, fenil ali (C1-C4) alkil, opcijsko substituiran z enim ali več atomi halogena; - C00Ri7, kjer je Ru H, (C1-C4) alkil, opcijsko substituiran z enim ali več atomi halogena, fenil ali benzil; in - (CH2)qORie, kjer q=1, 2, 3 ali 4 in Ri8 je H ali (C1-C4) cikloalkil; in farmacevtsko sprejemljive soli in N-oksidi na piridinskem obroču le-te.
  2. 2. Formulacija po zahtevku 1, ki obsega polnilo ali nosilec.
  3. 3. Formulacija po zahtevku 2, kjer je polnilo laktoza.
  4. 4. Enoodmerni ali večodmerni inhalator s suhim praškom, ki obsega formulacijo praška, ki jo je mogoče inhalirati, iz zahtevka 1.
  5. 5. Inhalator s suhim praškom po zahtevku 4, kjer se prašek polni v želatinske, plastične ali druge kapsule, vložke ali pretisne omote ali v rezervoir.
  6. 6. Odmerna aerosolna formulacija, vsebujoča potisni plin, ki obsega spojino s splošno formulo (II), kot je definirano v zahtevku 1.
  7. 7. Formulacija po zahtevku 6, kjer je omenjeni potisni plin hidrofluoroalkan.
  8. 8. Formulacija po zahtevkih 6 ali 7, kjer je spojina v obliki raztopine ali v dispergirani obiki.
  9. 9. Formulacija po zahtevkih 6 do 8, ki vsebuje so-topila, stabilizatorje in opcijsko druge ekscipiente.
  10. 10. Formulacija brez potisnega plina, ki jo je mogoče inhalirati, ki obsega spojino s splošno formulo (II), kot je definirano v zahtevku 1.
  11. 11. Formulacija po zahtevku 10, kjer so spojine izuma v obliki raztopin ali suspenzij v vodnem, alkoholnem ali vodno-alkoholnem mediju.
SI200831909T 2007-08-08 2008-07-17 Derivati 1-fenil-2-piridinil alkil alkoholov kot inhibitorji fosfodiesteraze SI2947068T1 (sl)

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EP07114019A EP2022783A1 (en) 2007-08-08 2007-08-08 "Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors"
EP15164929.0A EP2947068B1 (en) 2007-08-08 2008-07-17 Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors

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Families Citing this family (31)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
NO2560611T3 (sl) 2010-04-21 2018-06-02
KR101803121B1 (ko) * 2010-08-03 2017-11-29 키에시 파르마슈티시 엣스. 피. 에이. 포스포디에스테라제 억제제를 포함하는 약학적 제제
EP2600830B1 (en) * 2010-08-03 2018-02-21 Chiesi Farmaceutici S.p.A. Dry powder formulation comprising a phosphodiesterase inhibitor
PL2621494T3 (pl) * 2010-09-30 2019-04-30 Chiesi Farm Spa Zastosowanie stearynianu magnezu w preparatach w postaci suchego proszku do inhalacji
US20130005716A1 (en) * 2011-06-06 2013-01-03 Chiesi Farmaceutici S.P.A. Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors
WO2013045280A1 (en) 2011-09-26 2013-04-04 Chiesi Farmaceutici S.P.A. Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors
KR20140078719A (ko) 2011-10-21 2014-06-25 키에시 파르마슈티시 엣스. 피. 에이. 포스포디에스테라제 억제제로서 1-페닐-2-피리디닐 알킬 알코올의 유도체
BR112014029642A2 (pt) 2012-06-04 2017-06-27 Chiesi Farm Spa composto, combinação de um composto, composição farmacêutica, uso de um composto, dispositivo e kit
CN104822669A (zh) 2012-12-05 2015-08-05 奇斯药制品公司 作为pde-4抑制剂的苯基乙基吡啶衍生物
CN104822671B (zh) * 2012-12-05 2017-10-31 奇斯药制品公司 作为pde4抑制剂的苯乙基吡啶衍生物
RU2015121043A (ru) * 2012-12-05 2017-01-11 КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. Производные фенилэтилпиридина в качестве ингибиторов PDE-4
TR201907092T4 (tr) * 2012-12-05 2019-06-21 Chiesi Farm Spa Fosfodiesteraz inhibitörleri olarak 1-fenil-2-piridinil alkil alkol türevleri.
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
SI3587400T1 (sl) * 2013-10-22 2024-05-31 Chiesi Farmaceutici S.P.A. Postopek za pripravo zaviralca pde4
RU2016121854A (ru) * 2013-12-05 2017-12-07 КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. Производные гетероарила
US9145409B2 (en) * 2013-12-05 2015-09-29 Chiesi Farmaceutici S.P.A Benzhydryl derivatives
US10087176B2 (en) 2014-06-04 2018-10-02 Chiesi Farmaceutici S.P.A. 3,5-dichloro,4-(3,4-(cyclo-)alkoxyphenyl)--2-carbonyloxy)ethyl)pyridine derivatives as PDE-4 inhibitors
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
US9763924B2 (en) 2014-06-05 2017-09-19 Chiesi Farmaceutici S.P.A. Aminoester derivatives
US9326976B2 (en) * 2014-06-05 2016-05-03 Chiesi Farmaceutici S.P.A. Carbamate derivatives
TW201710254A (zh) * 2015-06-01 2017-03-16 吉斯藥品公司 胺基酯衍生物
WO2019129586A1 (en) 2017-12-28 2019-07-04 Chiesi Farmaceutici S.P.A. Use of 1-phenyl-2-pyridinyl alkyl alcohol derivatives for treating cystic fibrosis
WO2020217510A1 (ja) 2019-04-26 2020-10-29 株式会社Ｆｕｊｉ 印刷パラメータ取得装置および印刷パラメータ取得方法
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
WO2023208982A1 (en) 2022-04-27 2023-11-02 Chiesi Farmaceutici S.P.A. Crystal form of a pde4 inhibitor
WO2024027901A1 (en) 2022-08-02 2024-02-08 Chiesi Farmaceutici S.P.A. Predictive biomarker of clinical response to a pde4 inhibitor
WO2024062005A1 (en) 2022-09-22 2024-03-28 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
WO2024062007A1 (en) 2022-09-22 2024-03-28 Chiesi Farmaceutici S.P.A. Capsule inhaler for the administration of a phosphodiesterase-4 inhibitor

Family Cites Families (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5124455A (en) * 1990-08-08 1992-06-23 American Home Products Corporation Oxime-carbamates and oxime-carbonates as bronchodilators and anti-inflammatory agents
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
ATE282025T1 (de) 1992-07-28 2004-11-15 Aventis Pharma Ltd Inhibitoren von c-amp phosphodiesterase
US5786354A (en) * 1994-06-21 1998-07-28 Celltech Therapeutics, Limited Tri-substituted phenyl derivatives and processes for their preparation
GB9412573D0 (en) * 1994-06-22 1994-08-10 Celltech Ltd Chemical compounds
DE69712631D1 (de) 1996-09-17 2002-06-20 Merck & Co Inc Verfahren zur herstellung von phosphodiesterase iv inhibitoren
WO2000050402A1 (en) 1999-02-25 2000-08-31 Merck Frosst Canada & Co. Pde iv inhibiting compounds, compositions and methods of treatment
KR20050111759A (ko) 2003-03-12 2005-11-28 셀진 코포레이션 7-아미노-이소인돌릴 화합물 및 그의 제약학적 용도
TW200420554A (en) 2003-03-31 2004-10-16 Kyowa Hakko Kogyo Kk A intra-airway administrating preparation
US7888381B2 (en) * 2005-06-14 2011-02-15 Bristol-Myers Squibb Company Modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity, and use thereof
DE602007012105D1 (de) * 2006-07-14 2011-03-03 Chiesi Farma Spa Derivate von 1-phenyl-2-pyridinylalkylenalkohole als phosphodiesteraseinhibitoren
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
EP2600830B1 (en) 2010-08-03 2018-02-21 Chiesi Farmaceutici S.p.A. Dry powder formulation comprising a phosphodiesterase inhibitor
KR101803121B1 (ko) 2010-08-03 2017-11-29 키에시 파르마슈티시 엣스. 피. 에이. 포스포디에스테라제 억제제를 포함하는 약학적 제제
US20130005716A1 (en) 2011-06-06 2013-01-03 Chiesi Farmaceutici S.P.A. Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors
WO2013045280A1 (en) 2011-09-26 2013-04-04 Chiesi Farmaceutici S.P.A. Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors
KR20140078719A (ko) 2011-10-21 2014-06-25 키에시 파르마슈티시 엣스. 피. 에이. 포스포디에스테라제 억제제로서 1-페닐-2-피리디닐 알킬 알코올의 유도체
BR112014029642A2 (pt) 2012-06-04 2017-06-27 Chiesi Farm Spa composto, combinação de um composto, composição farmacêutica, uso de um composto, dispositivo e kit

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