JP2014037426A5 - - Google Patents
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- Publication number
- JP2014037426A5 JP2014037426A5 JP2013212664A JP2013212664A JP2014037426A5 JP 2014037426 A5 JP2014037426 A5 JP 2014037426A5 JP 2013212664 A JP2013212664 A JP 2013212664A JP 2013212664 A JP2013212664 A JP 2013212664A JP 2014037426 A5 JP2014037426 A5 JP 2014037426A5
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- substituted
- hydrogen atoms
- branched
- linear
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000005843 halogen group Chemical group 0.000 claims 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 19
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 17
- 150000001875 compounds Chemical class 0.000 claims 15
- 125000000217 alkyl group Chemical group 0.000 claims 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 4
- 229920006395 saturated elastomer Polymers 0.000 claims 4
- MSYGAHOHLUJIKV-UHFFFAOYSA-N 3,5-dimethyl-1-(3-nitrophenyl)-1h-pyrazole-4-carboxylic acid ethyl ester Chemical compound CC1=C(C(=O)OCC)C(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 MSYGAHOHLUJIKV-UHFFFAOYSA-N 0.000 claims 3
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims 3
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- -1 - (C 1 -C 4 ) alkyl R 10 Chemical compound 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- 150000001204 N-oxides Chemical class 0.000 claims 2
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 125000004429 atom Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 229910052801 chlorine Inorganic materials 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 claims 1
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims 1
- 125000006709 (C5-C7) cycloalkenyl group Chemical group 0.000 claims 1
- KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims 1
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims 1
- IGFDIFLMMLWKKY-UHFFFAOYSA-N 3-(cyclopropylmethoxy)-4-(difluoromethoxy)benzoic acid Chemical compound OC(=O)C1=CC=C(OC(F)F)C(OCC2CC2)=C1 IGFDIFLMMLWKKY-UHFFFAOYSA-N 0.000 claims 1
- 208000000884 Airway Obstruction Diseases 0.000 claims 1
- 206010006458 Bronchitis chronic Diseases 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 229940121948 Muscarinic receptor antagonist Drugs 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims 1
- 206010037211 Psychomotor hyperactivity Diseases 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 150000001298 alcohols Chemical class 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 206010006451 bronchitis Diseases 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000000812 cholinergic antagonist Substances 0.000 claims 1
- 208000007451 chronic bronchitis Diseases 0.000 claims 1
- 229940126543 compound 14 Drugs 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 229960001334 corticosteroids Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 239000003149 muscarinic antagonist Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 0 CC1(*)C=NC=CC(CC(c(cc2)cc(O*)c2O*)OC(**)=O)=C1 Chemical compound CC1(*)C=NC=CC(CC(c(cc2)cc(O*)c2O*)OC(**)=O)=C1 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07114019.8 | 2007-08-08 | ||
| EP07114019A EP2022783A1 (en) | 2007-08-08 | 2007-08-08 | "Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors" |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010519351A Division JP2010535722A (ja) | 2007-08-08 | 2008-07-17 | ホスホジエステラーゼ阻害剤としての１−フェニル−２−ピリジニルアルキルアルコールの誘導体 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015094698A Division JP6023846B2 (ja) | 2007-08-08 | 2015-05-07 | ホスホジエステラーゼ阻害剤としての１−フェニル−２−ピリジニルアルキルアルコールの誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014037426A JP2014037426A (ja) | 2014-02-27 |
| JP2014037426A5 true JP2014037426A5 (enExample) | 2014-04-10 |
| JP5746298B2 JP5746298B2 (ja) | 2015-07-08 |
Family
ID=38754730
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010519351A Ceased JP2010535722A (ja) | 2007-08-08 | 2008-07-17 | ホスホジエステラーゼ阻害剤としての１−フェニル−２−ピリジニルアルキルアルコールの誘導体 |
| JP2013212664A Active JP5746298B2 (ja) | 2007-08-08 | 2013-10-10 | ホスホジエステラーゼ阻害剤としての１−フェニル−２−ピリジニルアルキルアルコールの誘導体 |
| JP2015094698A Active JP6023846B2 (ja) | 2007-08-08 | 2015-05-07 | ホスホジエステラーゼ阻害剤としての１−フェニル−２−ピリジニルアルキルアルコールの誘導体 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010519351A Ceased JP2010535722A (ja) | 2007-08-08 | 2008-07-17 | ホスホジエステラーゼ阻害剤としての１−フェニル−２−ピリジニルアルキルアルコールの誘導体 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015094698A Active JP6023846B2 (ja) | 2007-08-08 | 2015-05-07 | ホスホジエステラーゼ阻害剤としての１−フェニル−２−ピリジニルアルキルアルコールの誘導体 |
Country Status (37)
Families Citing this family (32)
| 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 |
| HRP20180488T1 (hr) | 2010-04-21 | 2018-07-13 | Chiesi Farmaceutici S.P.A. | Postupak priprave čestica sa smanjenim elektrostatičkim nabojem |
| EP2600829B1 (en) | 2010-08-03 | 2017-06-14 | Chiesi Farmaceutici S.p.A. | Pharmaceutical formulation comprising a phosphodiesterase inhibitor |
| ES2664175T3 (es) * | 2010-08-03 | 2018-04-18 | Chiesi Farmaceutici S.P.A. | Formulación de polvo seco que comprende un inhibidor de fosfodiesterasa |
| PL2621494T3 (pl) | 2010-09-30 | 2019-04-30 | Chiesi Farm Spa | Zastosowanie stearynianu magnezu w preparatach w postaci suchego proszku do inhalacji |
| SG195319A1 (en) * | 2011-06-06 | 2013-12-30 | Chiesi Farma Spa | 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 |
| WO2013057013A2 (en) | 2011-10-21 | 2013-04-25 | Chiesi Farmaceutici S.P.A. | Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors |
| RU2637945C2 (ru) * | 2012-06-04 | 2017-12-08 | КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. | Производные 1-фенил-2-пиридинил-алкиловых спиртов в качестве ингибиторов фосфодиэстеразы |
| EP2928883B1 (en) | 2012-12-05 | 2018-02-14 | Chiesi Farmaceutici S.p.A. | Phenylethylpyridine derivatives as pde4-inhibitors and muscarinic receptor antagonists |
| 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 |
| CA2893663A1 (en) * | 2012-12-05 | 2014-06-12 | Chiesi Farmaceutici S.P.A. | Phenylethylpyridine derivatives as pde4-inhibitors |
| KR102192739B1 (ko) | 2012-12-05 | 2020-12-18 | 키에시 파르마슈티시 엣스. 피. 에이. | 포스포디에스테라제 억제제로서 1-페닐-2-피리디닐 알킬 알코올의 유도체 |
| 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 |
| SI3060551T1 (sl) * | 2013-10-22 | 2019-11-29 | Chiesi Farm Spa | Postopek za pripravo inhibitorja PDE4 |
| 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 |
| EP3077385B1 (en) * | 2013-12-05 | 2017-10-04 | Chiesi Farmaceutici S.p.A. | Heteroaryl derivatives for the treatment of respiratory diseases |
| 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 |
| 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 |
| 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 |
| 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 |
| US11794466B2 (en) | 2019-04-26 | 2023-10-24 | Fuji Corporation | Printing parameter acquisition device and printing parameter acquisition method |
| US12247674B2 (en) * | 2021-01-18 | 2025-03-11 | Chad Heffernan | Eclipse valve assembly |
| CN118475343A (zh) | 2021-12-21 | 2024-08-09 | 凯西制药公司 | 填充在具有改善的耐湿性的吸入器中的干粉制剂 |
| 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 |
| CA3267958A1 (en) | 2022-09-22 | 2024-03-28 | Chiesi Farm Spa | CAPSULE INHALATOR FOR THE ADMINISTRATION OF A PHOSPHODIESTERASE-4 INHIBITOR |
| KR20250069948A (ko) | 2022-09-22 | 2025-05-20 | 키에시 파르마슈티시 엣스. 피. 에이. | 포스포다이에스테라제-4 억제제의 투여를 위한 캡슐 흡입기 |
| EP4590271A1 (en) | 2022-09-22 | 2025-07-30 | Chiesi Farmaceutici S.p.A. | Capsule inhaler for the administration of a phosphodiesterase-4 inhibitor |
Family Cites Families (21)
| 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 |
| JP3775684B2 (ja) | 1992-07-28 | 2006-05-17 | ローン−プーラン・ロレ・リミテツド | 脂肪族−またはヘテロ原子−含有連結基によりアリールまたはヘテロアリールに連結されたフェニル含有化合物 |
| 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 |
| WO1998012178A1 (en) | 1996-09-17 | 1998-03-26 | Merck & Co., Inc. | Method of preparing phosphodiesterase iv inhibitors |
| AU764005B2 (en) | 1999-02-25 | 2003-08-07 | Merck Frosst Canada & Co. | PDE IV inhibiting compounds, compositions and methods of treatment |
| NZ542671A (en) | 2003-03-12 | 2008-12-24 | Celgene Corp | 7-Amido-isoindolyl compounds and their pharmaceutical uses |
| JPWO2004096274A1 (ja) | 2003-03-31 | 2006-07-13 | 協和醗酵工業株式会社 | 気道内投与剤 |
| 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 |
| EP2600829B1 (en) | 2010-08-03 | 2017-06-14 | Chiesi Farmaceutici S.p.A. | Pharmaceutical formulation comprising a phosphodiesterase inhibitor |
| ES2664175T3 (es) | 2010-08-03 | 2018-04-18 | Chiesi Farmaceutici S.P.A. | Formulación de polvo seco que comprende un inhibidor de fosfodiesterasa |
| SG195319A1 (en) | 2011-06-06 | 2013-12-30 | Chiesi Farma Spa | 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 |
| WO2013057013A2 (en) | 2011-10-21 | 2013-04-25 | Chiesi Farmaceutici S.P.A. | Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors |
| RU2637945C2 (ru) | 2012-06-04 | 2017-12-08 | КЬЕЗИ ФАРМАЧЕУТИЧИ С.п.А. | Производные 1-фенил-2-пиридинил-алкиловых спиртов в качестве ингибиторов фосфодиэстеразы |
-
2007
- 2007-08-08 EP EP07114019A patent/EP2022783A1/en not_active Withdrawn
-
2008
- 2008-07-17 RS RS20160145A patent/RS54606B1/sr unknown
- 2008-07-17 AU AU2008286027A patent/AU2008286027B2/en active Active
- 2008-07-17 NO NO15164929A patent/NO2947068T3/no unknown
- 2008-07-17 KR KR1020107002838A patent/KR101200683B1/ko active Active
- 2008-07-17 CA CA2695580A patent/CA2695580C/en active Active
- 2008-07-17 PT PT151649290T patent/PT2947068T/pt unknown
- 2008-07-17 PL PL08784827T patent/PL2185515T3/pl unknown
- 2008-07-17 EP EP15164929.0A patent/EP2947068B1/en active Active
- 2008-07-17 HU HUE15164929A patent/HUE035557T2/en unknown
- 2008-07-17 RS RS20180021A patent/RS56765B1/sr unknown
- 2008-07-17 JP JP2010519351A patent/JP2010535722A/ja not_active Ceased
- 2008-07-17 LT LTEP15164929.0T patent/LT2947068T/lt unknown
- 2008-07-17 MX MX2010001544A patent/MX2010001544A/es active IP Right Grant
- 2008-07-17 DK DK15164929.0T patent/DK2947068T3/en active
- 2008-07-17 HU HUE08784827A patent/HUE027171T2/en unknown
- 2008-07-17 HR HRP20160292TT patent/HRP20160292T1/hr unknown
- 2008-07-17 MY MYPI20100536 patent/MY152692A/en unknown
- 2008-07-17 DK DK08784827.1T patent/DK2185515T3/en active
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