HRP20180212T1 - Derivati 1-fenil-2-piridinilalkil-alkohola kao inhibitori fosfodiesteraze - Google Patents

Derivati 1-fenil-2-piridinilalkil-alkohola kao inhibitori fosfodiesteraze Download PDF

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Publication number
HRP20180212T1
HRP20180212T1 HRP20180212TT HRP20180212T HRP20180212T1 HR P20180212 T1 HRP20180212 T1 HR P20180212T1 HR P20180212T T HRP20180212T T HR P20180212TT HR P20180212 T HRP20180212 T HR P20180212T HR P20180212 T1 HRP20180212 T1 HR P20180212T1
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Croatia
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alkyl
substituted
halogen atoms
branched
linear
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HRP20180212TT
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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 HRP20180212T1 publication Critical patent/HRP20180212T1/hr

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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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    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
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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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    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • 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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    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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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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    • A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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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
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
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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
    • C07D213/60—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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    • 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
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    • C07D473/08—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1 and 3, e.g. theophylline

Claims (11)

1. Formulacija praška za inhalaciju koja sadrži spoj opće formule (II) [image] (II) u kojoj: Z jest odabran iz skupine koju čine (CH2)m gdje m = 0, 1 ili 2; i CR4R5 gdje R4 jest neovisno odabran od H ili linearnog ili razgranatog (C1–C4) alkila koji može biti supstituiran s jednim ili više atoma halogena ili (C1–C4) cikloalkilom te R5 je neovisno odabran iz skupine koju čine – linearni ili razgranati (C1–C4) alkil koji može biti supstituiran s jednim ili više atoma halogena; – fenil; – benzil; – NH2; te – HNCOOR’, gdje je R’ linearni ili razgranati (C1–C4) alkil koji može biti supstituiran s jednim ili više atoma halogena. R1 i R2 su različiti ili isti i neovisno su odabrani iz skupine koju čine – H; – linearni ili razgranati (C1–C6) alkil, koji može biti supstituiran s jednim ili više supstituenata odabranim od atoma halogena, (C3–C7) cikloalkila ili (C5–C7) cikloalkenila; – (C3–C7) cikloalkil; – (C5–C7) cikloalkenil; – linearni ili razgranati (C2–C6) alkenil; te – linearni ili razgranati (C2–C6) alkinil. A je fenil koji može biti supstituiran s jednom ili više Rx skupina, ili A jest heteroarilni prsten koji može biti supstituiran s jednom ili više Rx skupina, pri čemu A jest heteroarilni prsten odabran od skupine koju čine pirol, pirazol, furan, tiofen, imidazol, oksazol, izoksazol, tiazol, piridin, pirimidin, pirazin, piridazin, i piran, pri čemu opcionalnih supstituenata Rx na sustavu prstena A može biti jedan ili više, mogu biti isti ili različiti, i neovisno su odabrani iz skupine koju čine: – linearni ili razgranati (C1–C6) alkil koji može biti supstituiran s jednim ili više atoma halogena ili (C3–C7) cikloalkilom; – linearni ili razgranati (C2–C6) alkenil koji može biti supstituiran s jednim ili više (C3–C7) cikloalkilom; – linearni ili razgranati (C2–C6) alkinil koji može biti supstituiran s jednim ili više (C3–C7) cikloalkilom; – (C5–C7) cikloalkenil; – fenil; – (C3–C7) heterocikloalkil; – OR7 gdje je R7 odabran iz skupine koju čine – H; – (C1–C10) alkil koji može biti supstituiran s jednim ili više atoma halogena ili (C3–C7) cikloalkilom; – (C3–C7) cikloalkil; – (C1–C4) alkilen-( C3–C7) heterocikloalkil; – CO–(C1–C6) alkil, gdje (C1–C6) alkil može biti supstituiran s jednim ili više atoma halogena; – COO–(C1–C6) alkil, gdje (C1–C6) alkil može biti supstituiran s jednim ili više atoma halogena; – fenil; – benzil; – (C1–C10) alkil-NR8R9 gdje R8 i R9 jesuneovisno odabrani iz skupine koju čine H, linearni ili razgranati (C1–C6) alkil koji može biti supstituiran s jednim ili više atoma halogena te skupa s dušikovim atomom na koji su vezani tvore zasićeni, djelomično zasićeni ili nezasićeni prsten; te – atomi halogena; – CN; – NO2; – NR10R11 gdje su R10 i R11 različiti ili isti i neovisno su odabrani iz skupine koju čine – H; – linearni ili razgranati (C1-C6) alkil, koji može biti supstituiran s jednim ili više atoma halogena, fenil ili (C3–C7) cikloalkil; – COC6H5; – CO–(C1–C4) alkil, gdje (C1–C4) alkil može biti supstituiran s jednim ili više atoma halogena; – COO-(C1–C4) alkil, gdje (C1–C4) alkil može biti supstituiran s jednim ili više atoma halogena; – CONH–(C1–C6) alkil-R12, gdje je R12 odabran iz skupine koju čine – H; – (C1–C4) alkil koji može biti supstituiran s jednim ili više atoma halogena; – OR4R5; te –CONH(C1–C4) alkil–N(C1–C4) alkil, gdje N(C1–C4) alkil može biti supstituiran s jednim ili više atoma halogena; ili zajedno s dušikovim atomom na koji su vezani tvore zasićeni ili djelomično zasićeni prsten; –(C1–C4) alkil–NR10R11; – COR12 gdje R12 jest fenil ili linearni ili razgranati (C1-C6) alkil koji može biti supstituiran s jednim ili više atoma halogena; – okso; – HNSO2R13 gdje R13 jest (C1–C4) alkil koji može biti supstituiran s jednim ili više atoma halogena ili fenil koji može biti supstituiran s atomima halogena ili s (C1–C4) alkilnom skupinom koja može biti supstituirana s jednim ili više atoma halogena; – SO2R14 gdje R14 jest (C1–C4) alkil koji može biti supstituiran s jednim ili više atoma halogena, OH ili NR10R11 gdje R10 i R11 jesu kao gore definirani; – SOR15 gdje R15 jest fenil ili (C1–C4) alkil koji može biti supstituiran s jednim ili više atoma halogena; – SR16 gdje R16 jest H, fenil ili (C1–C4) alkil koji može biti supstituiran s jednim ili više atoma halogena; – COOR17 gdje R17 jest H, (C1–C4) alkil koji može biti supstituiran s jednim ili više atoma halogena, fenil ili benzil; te – (CH2)qOR18, gdje q=1, 2, 3 ili 4 te R18 jest H ili (C1–C4) cikloalkil, te farmaceutski prihvatljive soli i njihovi N-oksidi na piridinskom prstenu.
2. Formulacija prema patentnom zahtjevu 1, naznačeno time da sadrži razrjeđivač ili nosač.
3. Formulacija prema patentnom zahtjevu 2, naznačeno time da razrjeđivač jest laktoza.
4. Suhi prašak za inhalaciju u jednoj ili višestrukoj dozi koji sadrži formulaciju praška za inhalaciju prema patentnom zahtjevu 1.
5. Suhi prašak za inhalaciju prema patentnom zahtjevu 4, naznačeno time da je prašak punjen u želatinske, plastične ili druge kapsule, patrone ili pakiranja blistera ili u spremnike.
6. Aerosolna formulacija s propelantom koja se može odmjeriti, koja sadrži spoj opće formule (II) kako je definiran u patentnom zahtjevu 1.
7. Formulacija prema patentnom zahtjevu 6, naznačeno time da rečeni propelant jest hidrofluoralkan.
8. Formulacija prema patentnim zahtjevima 6 ili 7, naznačeno time da je spoj u otopini ili u dispergiranom obliku.
9. Formulacija prema patentnim zahtjevima 6 do 8, naznačeno time da sadrži kootapala, stabilizatore, a može i druge ekspicijense.
10. Formulacija za inhaliranje bez propelanta koja sadrži spoj opće formule (II) kako je definiran u patentnom zahtjevu 1.
11. Formulacija prema patentnom zahtjevu 10, naznačeno time da su spojevi iz izuma u obliku otopina ili suspenzija u vodenom, alkoholnom ili hidroalkoholnom mediju.
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