HRP20121004T1 - (1-fenil-2-piridin-4-il)etil-esteri benzojeve kiseline kao inhibitori fosfodiesteraze - Google Patents
(1-fenil-2-piridin-4-il)etil-esteri benzojeve kiseline kao inhibitori fosfodiesteraze Download PDFInfo
- Publication number
- HRP20121004T1 HRP20121004T1 HRP20121004AT HRP20121004T HRP20121004T1 HR P20121004 T1 HRP20121004 T1 HR P20121004T1 HR P20121004A T HRP20121004A T HR P20121004AT HR P20121004 T HRP20121004 T HR P20121004T HR P20121004 T1 HRP20121004 T1 HR P20121004T1
- Authority
- HR
- Croatia
- Prior art keywords
- image
- compound
- hnso2r4
- methyl
- formula
- Prior art date
Links
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 title claims 4
- 239000005711 Benzoic acid Substances 0.000 title claims 2
- 235000010233 benzoic acid Nutrition 0.000 title claims 2
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 title 1
- 239000002571 phosphodiesterase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- LJRXSWAYTGAJHV-UHFFFAOYSA-N 2,3-dichloro-4-methylpyridine Chemical compound CC1=CC=NC(Cl)=C1Cl LJRXSWAYTGAJHV-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 238000002360 preparation method Methods 0.000 claims 2
- HXHSSJUSVPPLRX-SNVBAGLBSA-N (2s)-2-hydroxy-3-oxo-2-phenylbutanoic acid Chemical compound CC(=O)[C@](O)(C(O)=O)C1=CC=CC=C1 HXHSSJUSVPPLRX-SNVBAGLBSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- IHOXNOQMRZISPV-YJYMSZOUSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-methoxyphenyl)propan-2-yl]azaniumyl]ethyl]-2-oxo-1h-quinolin-8-olate Chemical compound C1=CC(OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=C(O)C2=C1C=CC(=O)N2 IHOXNOQMRZISPV-YJYMSZOUSA-N 0.000 claims 1
- 206010012438 Dermatitis atopic Diseases 0.000 claims 1
- 150000001204 N-oxides Chemical class 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 239000005557 antagonist Substances 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 201000008937 atopic dermatitis Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229950010713 carmoterol Drugs 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 239000003246 corticosteroid Substances 0.000 claims 1
- 229960001334 corticosteroids Drugs 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- BPZSYCZIITTYBL-UHFFFAOYSA-N formoterol Chemical group C1=CC(OC)=CC=C1CC(C)NCC(O)C1=CC=C(O)C(NC=O)=C1 BPZSYCZIITTYBL-UHFFFAOYSA-N 0.000 claims 1
- 229960002848 formoterol Drugs 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical compound C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 210000002345 respiratory system Anatomy 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
- 238000005507 spraying Methods 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES 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
- A61M15/00—Inhalators
- A61M15/0065—Inhalators with dosage or measuring devices
-
- 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
-
- 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
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4704—2-Quinolinones, e.g. carbostyril
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES 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
- A61M16/00—Devices for influencing the respiratory system of patients by gas treatment, e.g. mouth-to-mouth respiration; Tracheal tubes
- A61M16/10—Preparation of respiratory gases or vapours
- A61M16/14—Preparation of respiratory gases or vapours by mixing different fluids, one of them being in a liquid phase
-
- 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
-
- 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
- A61P11/02—Nasal agents, e.g. decongestants
-
- 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
- A61P11/06—Antiasthmatics
-
- 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
-
- 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
-
- 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
-
- 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
- C07D213/24—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
-
- 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
-
- 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
Landscapes
- 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)
Claims (18)
1. (-)-Enantiomer spoja opće formule (I)
[image]
(I)
naznačen time da
n jest 0 ili 1,
R1 i R2 mogu biti isti ili različiti, a odabrani su od sljedeće skupine
- linearni ili razgranati C1-C6 alkil, koji može biti supstituiran s jednim ili više atoma halogena,
- OR3 u kojem R3 jest linearni ili razgranati C1-C6 alkil koji može biti supstituiran s jednim ili više atoma halogena
ili C3-C7 cikloalkilne skupine, te
- HNSO2R4 u kojem R4 jest linearni ili razgranati C1-C4 alkil koji može biti supstituiran s jednim ili više atoma halogena,
u kojem je najmanje jedan od R1 i R2 jest HNSO2R4, farmaceutski prihvatljive anorganske i organske soli, hidrati te solvati.
2. Spoj prema patentnom zahtjevu 1, naznačen time da R1 jest HNSO2R4, u kojem R4 jest metil, R2 je OR3, pri čemu R3 jest ciklopropilmetil te n jest 0.
3. Spoj prema patentnom zahtjevu 1, naznačen time da R1 jest HNSO2R4, u kojem R4 jest metil, R2 je OR3, pri čemu R3 jest ciklopropilmetil te n jest 1.
4. Spoj prema patentnom zahtjevu 1, naznačen time da R1 jest OR3, R2 je HNSO2R4 u kojem R4 jest metil te n jest 1.
5. Spoj prema patentnom zahtjevu 1, naznačen time da R1 jest metil, R2 je HNSO2R4 u kojem R4 jest metil te n jest 1.
6. Spoj prema patentnom zahtjevu 1, naznačen time da R1 u R2 jesu HNSO2R4, u kojima R4 jest metil, te n jest 0.
7. Spoj prema patentnom zahtjevu 1, naznačen time da R1 u R2 jesu HNSO2R4, u kojima R4 jest metil, te n jest 1.
8. Postupak priprave spojeva definiranih patentnim zahtjevima 1 do 7, naznačen time da obuhvaća korak reakcije aldehida (1)
[image]
(1)
s metildiklorpiridinom (2)
[image]
(2)
čime nastaje alkohol (3) koji može biti oksidiran u odgovarajući N-oksidni derivat (4),
[image]
(3)
kondenzaciju (3) ili (4) s kiralnom kiselinom kao što je (S)-naproksen ili (S)-acetilbademova kiselina čime nastaje dijastereomrna smjesa (10)
[image]
(10)
ili (5)
[image]
(5)
odjeljivanje dijastereomerne smjese (10) ili (5) i dva dijastereomera (11)
[image]
(11)
te (13)
[image]
(13)
ili (6)
[image]
(6)
te (8)
[image]
(8)
kromatografiju ili kristalizaciju čime nakon cijepanja alkohola nastaje (±) (14)
[image]
(14)
ili (+) (7)
[image]
(7)
te (-) (9)
[image]
(9)
te reakciju spoja (+) (14) ili (+) (7) s pogodnom benzojevom kiselinom (15)
[image]
(15)
čime nastaju spojevi opće formule (I) u kojima R1 i R2 jesu kao što su definirani u patentnom zahtijevu 1.
9. Spoj opće formule (II)
[image]
(II)
naznačen time da je n definiran u patentnom zahtjevu 1, a ugljikov atom naznačen zvjezdicom ima (S) konfoguraciju.
10. Kombinacija spoja formule (I) kao što je definirano u patentnim zahtjevima 1 do 7, naznačena time da je s drugom farmaceutski aktivnom komponentom odabranom od sljedećih: klasa �2 agonista, M3 antagnista i koritkosteroidi.
11. Kombinacija prema patentnom zahtjevu 10, naznačena time da aktivna komponenta jest formoterol ili karmoterol.
12. Farmaceutski pripravak, naznačen time da sadrži spoj formule (I) kao što je definirano u patentnim zahtjevima 1 do 7 ili kombinaciju prema patentnim zahtjevima 10 ili 11, te jedan ili više farmaceutski prihvatljivih nosača i/ili ekcipijensa.
13. Spoj formule (I) kao što je definiran u patentnim zahtjevima 1 do 7, naznačen time da je za lijek.
14. Spoj formule (I) kao što je definiran u patentnim zahtjevima 1 do 7, naznačen time da je za sprječavanje i liječenje bolesti respiratornog trakta karakteriziran opstrukcijom kao što je astma ili COPD.
15. Naprava, naznačena time da sadrži farmaceutski pripravak prema patentnom zahtjevu 12.
16. Paket, naznačen time da sadrži farmaceutski pripravak iz patentnog zahtijeva 12 u napravi koja može sadržavati jednu ili višestruku dozu praška za inhalaciju ili tlačeni inhalat ili pripravak za raspršivanje u inhalatoru.
17. Spoj formule (I) kao što je definiran u patentnim zahtjevima od 1 do 7, naznačena time da se koristi za sprječavanje i/ili liječenje alergijskog rinitisa.
18. Spoj formule (I) kao što je definiran u patentnim zahtjevima od 1 do 7, naznačena time da se koristi za sprječavanje i/ili liječenje atopičnog dermatititsa.
Applications Claiming Priority (2)
| 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 |
| PCT/EP2010/000676 WO2010089107A1 (en) | 2009-02-06 | 2010-02-04 | Benzoic acid (1-phenyl-2-pyridin-4-yl) ethyl esters as phosphodiesterase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20121004T1 true HRP20121004T1 (hr) | 2012-12-31 |
Family
ID=40674203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20121004AT HRP20121004T1 (hr) | 2009-02-06 | 2012-12-06 | (1-fenil-2-piridin-4-il)etil-esteri benzojeve kiseline kao inhibitori fosfodiesteraze |
Country Status (34)
| Country | Link |
|---|---|
| US (5) | US8440834B2 (hr) |
| EP (2) | EP2216327A1 (hr) |
| JP (2) | JP5612610B2 (hr) |
| KR (1) | KR101337728B1 (hr) |
| CN (1) | CN102317262B (hr) |
| AR (1) | AR075243A1 (hr) |
| AU (1) | AU2010211274B2 (hr) |
| BR (1) | BRPI1005695A8 (hr) |
| CA (1) | CA2751494C (hr) |
| CL (1) | CL2011001876A1 (hr) |
| CO (1) | CO6400217A2 (hr) |
| CY (1) | CY1113764T1 (hr) |
| EA (1) | EA019113B1 (hr) |
| ES (1) | ES2395528T3 (hr) |
| GE (1) | GEP20135919B (hr) |
| HK (1) | HK1162508A1 (hr) |
| HR (1) | HRP20121004T1 (hr) |
| IL (1) | IL214446A (hr) |
| JO (1) | JO2761B1 (hr) |
| MA (1) | MA33105B1 (hr) |
| ME (1) | ME02325B (hr) |
| MX (1) | MX2011007857A (hr) |
| MY (1) | MY152048A (hr) |
| NZ (1) | NZ594413A (hr) |
| PE (1) | PE20120055A1 (hr) |
| PL (1) | PL2393782T3 (hr) |
| PT (1) | PT2393782E (hr) |
| RS (1) | RS52605B (hr) |
| SG (1) | SG173208A1 (hr) |
| SI (1) | SI2393782T1 (hr) |
| TN (1) | TN2011000346A1 (hr) |
| TW (1) | TWI459945B (hr) |
| UA (1) | UA102574C2 (hr) |
| WO (1) | WO2010089107A1 (hr) |
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 |
| MA34449B1 (fr) * | 2010-08-03 | 2013-08-01 | Chiesi Farma Spa | Formulation de poudre seche comprenant un inhibiteur de phosphodiesterase |
| CN103052378A (zh) | 2010-08-03 | 2013-04-17 | 奇斯药制品公司 | 包含磷酸二酯酶抑制剂的药物制剂 |
| CN106946848B (zh) | 2011-06-06 | 2022-01-04 | 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 |
| CN103827088B (zh) * | 2011-09-26 | 2017-10-13 | 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 |
| WO2013057013A2 (en) | 2011-10-21 | 2013-04-25 | Chiesi Farmaceutici S.P.A. | Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors |
| WO2013087749A1 (en) * | 2011-12-16 | 2013-06-20 | Chiesi Farmaceutici S.P.A. | Potentiation induced by pde4 inhibitors in the treatment of leukemia |
| 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 |
| KR20150090253A (ko) * | 2012-12-05 | 2015-08-05 | 키에시 파르마슈티시 엣스. 피. 에이. | Pde4-억제제로서 페닐에틸피리딘 유도체 |
| PL2928869T3 (pl) | 2012-12-05 | 2019-08-30 | Chiesi Farmaceutici S.P.A. | Pochodne alkoholu 1-fenylo-2-pirydynyloalkilowego jako inhibitory fosfodiesterazy |
| EP2928880B1 (en) * | 2012-12-05 | 2018-02-14 | Chiesi Farmaceutici S.p.A. | Phenylethylpyridine derivatives as pde4-inhibitors and muscarinic receptor antagonists |
| WO2014086855A1 (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 |
| EP3293176B1 (en) | 2013-10-22 | 2020-12-02 | Chiesi Farmaceutici S.p.A. | Crystal form of a pde4 inhibitor |
| US9145409B2 (en) | 2013-12-05 | 2015-09-29 | Chiesi Farmaceutici S.P.A | Benzhydryl derivatives |
| TW201607944A (zh) | 2013-12-05 | 2016-03-01 | 吉斯藥品公司 | 雜芳基衍生物 |
| WO2015185128A1 (en) * | 2014-06-04 | 2015-12-10 | Chiesi Farmaceutici S.P.A. | 3,5-dichloro,4-(3,4-(cyclo-)alkoxyphenyl)- 2-carbonyloxy)ethyl)pyridine derivatives as pde-4 inhibitors |
| WO2015185130A1 (en) * | 2014-06-04 | 2015-12-10 | 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 |
| 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 |
| US20190275022A1 (en) * | 2016-07-20 | 2019-09-12 | Allergan, Inc. | Methods, compositions, and compounds for treatment of dermatological and ocular conditions |
| BR112020012972A2 (pt) * | 2017-12-28 | 2020-11-24 | Chiesi Farmaceutici S.P.A. | uso de derivados de álcool 1-fenil-2-piridinil alquílico para tratar fibrose cística |
| 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 |
| 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 |
| 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 (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW263495B (hr) * | 1992-12-23 | 1995-11-21 | Celltech Ltd | |
| GB9304919D0 (en) * | 1993-03-10 | 1993-04-28 | Celltech Ltd | Chemical compounds |
| SI0706513T1 (en) * | 1993-07-02 | 2002-10-31 | Altana Pharma Ag | Fluoroalkoxy-substituted benzamides and their use as cyclic nucleotide phosphodiesterase inhibitors |
| GB9412573D0 (en) * | 1994-06-22 | 1994-08-10 | Celltech Ltd | Chemical compounds |
| WO2008006509A1 (en) * | 2006-07-14 | 2008-01-17 | Chiesi Farmaceutici S.P.A. | Derivatives of 1-phenyl-2-pyridynyl alkylene alcohols as phosphodiesterase inhibitors |
| 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 |
| CN103052378A (zh) | 2010-08-03 | 2013-04-17 | 奇斯药制品公司 | 包含磷酸二酯酶抑制剂的药物制剂 |
| MA34449B1 (fr) | 2010-08-03 | 2013-08-01 | Chiesi Farma Spa | Formulation de poudre seche comprenant un inhibiteur de phosphodiesterase |
| CN106946848B (zh) | 2011-06-06 | 2022-01-04 | 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 |
| CN103827088B (zh) | 2011-09-26 | 2017-10-13 | 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 |
| WO2013057013A2 (en) | 2011-10-21 | 2013-04-25 | Chiesi Farmaceutici S.P.A. | Derivatives of 1-phenyl-2-pyridinyl alkyl alcohols as phosphodiesterase inhibitors |
| 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 |
| PL2928869T3 (pl) | 2012-12-05 | 2019-08-30 | Chiesi Farmaceutici S.P.A. | Pochodne alkoholu 1-fenylo-2-pirydynyloalkilowego jako inhibitory fosfodiesterazy |
-
2009
- 2009-02-06 EP EP09001660A patent/EP2216327A1/en not_active Withdrawn
-
2010
- 2010-02-03 JO JO201033A patent/JO2761B1/en active
- 2010-02-04 EP EP10704746A patent/EP2393782B1/en active Active
- 2010-02-04 UA UAA201108827A patent/UA102574C2/ru unknown
- 2010-02-04 CN CN201080006643.7A patent/CN102317262B/zh active Active
- 2010-02-04 MY MYPI2011003639 patent/MY152048A/en unknown
- 2010-02-04 AU AU2010211274A patent/AU2010211274B2/en active Active
- 2010-02-04 ME MEP-2016-19A patent/ME02325B/me unknown
- 2010-02-04 SI SI201030094T patent/SI2393782T1/sl unknown
- 2010-02-04 MX MX2011007857A patent/MX2011007857A/es active IP Right Grant
- 2010-02-04 PE PE2011001441A patent/PE20120055A1/es active IP Right Grant
- 2010-02-04 NZ NZ594413A patent/NZ594413A/xx unknown
- 2010-02-04 BR BRPI1005695A patent/BRPI1005695A8/pt not_active Application Discontinuation
- 2010-02-04 JP JP2011548600A patent/JP5612610B2/ja active Active
- 2010-02-04 EA EA201190099A patent/EA019113B1/ru unknown
- 2010-02-04 TW TW099103291A patent/TWI459945B/zh active
- 2010-02-04 GE GEAP201012324A patent/GEP20135919B/en unknown
- 2010-02-04 SG SG2011056165A patent/SG173208A1/en unknown
- 2010-02-04 PL PL10704746T patent/PL2393782T3/pl unknown
- 2010-02-04 AR ARP100100311A patent/AR075243A1/es not_active Application Discontinuation
- 2010-02-04 WO PCT/EP2010/000676 patent/WO2010089107A1/en active Application Filing
- 2010-02-04 PT PT107047466T patent/PT2393782E/pt unknown
- 2010-02-04 MA MA34150A patent/MA33105B1/fr unknown
- 2010-02-04 KR KR1020117016842A patent/KR101337728B1/ko active IP Right Grant
- 2010-02-04 RS RS20120547A patent/RS52605B/en unknown
- 2010-02-04 CA CA2751494A patent/CA2751494C/en active Active
- 2010-02-04 ES ES10704746T patent/ES2395528T3/es active Active
- 2010-02-05 US US12/700,926 patent/US8440834B2/en active Active
-
2011
- 2011-07-13 TN TN2011000346A patent/TN2011000346A1/fr unknown
- 2011-08-04 IL IL214446A patent/IL214446A/en active IP Right Grant
- 2011-08-04 CO CO11098671A patent/CO6400217A2/es not_active Application Discontinuation
- 2011-08-04 CL CL2011001876A patent/CL2011001876A1/es unknown
-
2012
- 2012-03-28 HK HK12103106.1A patent/HK1162508A1/xx unknown
- 2012-09-14 US US13/618,346 patent/US20130012487A1/en not_active Abandoned
- 2012-12-04 CY CY20121101183T patent/CY1113764T1/el unknown
- 2012-12-06 HR HRP20121004AT patent/HRP20121004T1/hr unknown
-
2013
- 2013-06-28 US US13/930,304 patent/US8648204B2/en active Active
- 2013-12-17 US US14/108,731 patent/US8859778B2/en active Active
-
2014
- 2014-09-04 JP JP2014179895A patent/JP2015038079A/ja active Pending
- 2014-09-10 US US14/482,287 patent/US9056176B2/en active Active
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20121004T1 (hr) | (1-fenil-2-piridin-4-il)etil-esteri benzojeve kiseline kao inhibitori fosfodiesteraze | |
| HRP20181048T1 (hr) | Neuroaktivni 19-alkoksi-17-supstituirani steroidi, korisni u postupcima liječenja | |
| HRP20110445T1 (hr) | Spojevi bisadenozina kao agonisti receptora adenozina a2a | |
| HRP20160292T1 (hr) | Derivati 1-fenil-2-piridinilalkil-alkohola kao inhibitori fosfodiesteraze | |
| RU2012149633A (ru) | Органические соединения | |
| JP2017531019A5 (hr) | ||
| MY180666A (en) | Substituted pyrazolo [3,4-b] pyridines as medicaments | |
| IN2014MN01839A (hr) | ||
| HRP20130213T1 (hr) | Spojevi morfinana | |
| JP2004511512A (ja) | 認識障害の治療のためのアセチルコリンエステラーゼ阻害薬およびｇａｂａａ反作用薬の組合せ使用 | |
| BRPI0714320A2 (pt) | Derivado de imidazo[1,2-a] piridina-2-carboxamidas, sua preparação e sua aplicação em terapêutica | |
| WO2012016845A3 (en) | Pharmaceutical formulation comprising a phosphodiesterase inhibitor | |
| JP2011500621A5 (hr) | ||
| AR086100A1 (es) | Compuestos de cromenona y composiciones farmaceuticas que los contienen | |
| EA032951B1 (ru) | Производное глутаримидов, его применение, фармацевтическая композиция на его основе, способ его получения | |
| EP2607363A4 (en) | CONDENSED RING COMPOUND FOR USE AS MINERALOCORTICOID RECEPTOR ANTAGONISTS | |
| TW201217338A (en) | Crystalline oxalate salts of a diamide compound | |
| HRP20121074T1 (hr) | Derivati kinolina i njihovi farmaceutski sastavi | |
| WO2020160225A1 (en) | ESTROGEN RECEPTOR BETA (ERβ) AGONISTS FOR THE TREATMENT OF FIBROTIC CONDITIONS | |
| PE20220964A1 (es) | Derivados de n-metil, n-(6-(metoxi)piridazin-3-il) amina como moduladores de autotaxina (atx) para el tratamiento de enfermedades inflamatorias de las vias respiratorias o fibroticas | |
| RU2016137349A (ru) | Успокоительный феромон для кошек | |
| WO2011113852A3 (fr) | Nouvelles utilisations de composes de type esteramide | |
| RU2012131280A (ru) | [4-(5-аминометил-2-фторфенил)пиперидин-1-ил]-(1н-пирролопиридинил)метаноны и их синтез | |
| JP2017526719A5 (hr) | ||
| MX2023009961A (es) | Compuestos heterociclicos antivirales. |