HRP20140585T1 - Inovativni inhibitori fosfodiesteraze - Google Patents

Inovativni inhibitori fosfodiesteraze Download PDF

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Publication number
HRP20140585T1
HRP20140585T1 HRP20140585AT HRP20140585T HRP20140585T1 HR P20140585 T1 HRP20140585 T1 HR P20140585T1 HR P20140585A T HRP20140585A T HR P20140585AT HR P20140585 T HRP20140585 T HR P20140585T HR P20140585 T1 HRP20140585 T1 HR P20140585T1
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compound
methoxy
ethanone
spiro
dichloropyridin
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HRP20140585AT
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Jakob Felding
Simon Feldbak Nielsen
Jens Christian Hojland Larsen
Bollu Ravindra Babu
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Leo Pharma A/S
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/10—Spiro-condensed systems
    • 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
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/357—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having two or more oxygen atoms in the same ring, e.g. crown ethers, guanadrel
    • A61K31/36—Compounds containing methylenedioxyphenyl groups, e.g. sesamin
    • 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
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • 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
    • A61P17/04—Antipruritics
    • 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
    • A61P17/06—Antipsoriatics
    • 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
    • A61P17/08—Antiseborrheics
    • 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
    • A61P17/14—Drugs for dermatological disorders for baldness or alopecia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • 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
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/10—Spiro-condensed systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • Pain & Pain Management (AREA)
  • Pulmonology (AREA)
  • Rheumatology (AREA)
  • Immunology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Claims (26)

1. Spoj općenite formule I [image] gdje m i n neovisno predstavljaju 0, 1, 2, 3, 4, 5, 6, ili 7; i gdje G i E neovisno predstavljaju sumpor, kisik, -N(R5)-, ili -N(R5)C(O)-, a R1 i R2, zajedno s atomom ugljika na koji su vezani, tvore jedan heterociklički prsten koji sadrži jedan ili dva heteroatoma odabrana iz skupine koju čine kisik, sumpor, -S(O)-, -S(O)2-, -N=, -N(R5)-, pri čemu su jedan ili više atoma ugljika u spomenutom heterocikličkom prstenu opcionalno supstituirani jednim ili više, istih ili različitih supstituenata odabranih iz R4; R3 je halogen hidroksi, C1-6-alkil, C2-6-alkenil, C2-6-alkinil, halo-C1-6-alkil, C1-6-alkoksi, halo-C1-6-alkoksi, C1-6-alkiltio, formil, C1-6-alkoksikarbonil, C1-6-alkilkarbonil, ili aminokarbonil; R4 je hidrogen, amino, tiokso, C1-6-alkil, halo-C1-6-alkil, hidroksi-C1-6-alkil, C1-6-alkoksi, halogen, okso ili hidroksi; R5 je hidrogen, C1-6-alkil, halo-C1-6-alkil, C1-6-alkilkarbonil, hidroksi-C1-6-alkil, C1-6-alkoksikarbonil, C1-6-alkilsulfonil, C1-6-alkilaminosulfonil ili aminosulfonil; X je jedna veza, -CH2-, ili -NH-; A je aril koji sadrži 6-10 atoma ugljika, C3-10-cikloalkil, C3-10-cikloalkenil, aril-C1-6-alkil, heteroaril koji sadrži 1-10 atoma ugljika i 1-5 heteroatoma, heteroaril-C1-6-alkil, heteroaril koji sadrži 1-10 atoma ugljika i 1-5 heteroatoma, hetero-C3-10-cikloalkil koji sadrži 1-3 heteroatoma ili hetero-C3-10-cikloalkenil koji sadrži 1-3 heteroatoma, opcionalno supstituiranih jednim ili više, istih ili različitih supstituenata odabranih iz R4; i njihove farmaceutski prihvatljive soli, hidrati, N-oksidi ili solvati.
2. Spoj prema zahtjevu 1, naznačen time da su i E i G kisik.
3. Spoj prema zahtjevu 1 ili 2, naznačen time da su i „m“ i „n“ jedan.
4. Spoj prema zahtjevu 1 ili 2, naznačen time da su i „m“ i „n“ nula.
5. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time da R1 i R2, zajedno s atomom ugljika na koji su spojeni, tvore jedan 4-, 5- ili 6-člani heterociklički prsten.
6. Spoj prema zahtjevu 5, naznačen time da je taj heterociklički prsten tetrahidropiran, oksetan, [1,3]dioksolan, [1,3]dioksan, tetrahidrotiopiran, tetrahidrotiopiran-1,1-dioksid, tetrahidrotiopiran-1-oksid, piperidin, tetrahidrotiofen, [1,3]-ditian, tietan, [1,3]-ditian-1,3-dioksid, tietan-1-oksid, ili tietan-1,1-dioksid.
7. Spoj prema zahtjevu 5, naznačen time da heterociklički prsten sadrži jedan heteroatom.
8. Spoj prema zahtjevu 5, naznačen time da heterociklički prsten sadrži dva heteroatoma.
9. Spoj prema zahtjevu 7 ili 8, naznačen time da je/su taj/ti heteroatom(i) kisik.
10. Spoj prema zahtjevu 7 ili 8, naznačen time da je/su taj/ti heteroatom(i) sumpor, -S(O)-, ili -S(O)2-.
11. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time da je A heteroaril koji sadrži 1-10 atoma ugljika i 1-5 heteroatoma ili heteroaril-C1-6-alkil, a taj heteroaril sadrži 1-10 atoma ugljika i 1-5 heteroatoma.
12. Spoj prema zahtjevu 11, naznačen time da je A piridil, pirazinil ili kvinolil.
13. Spoj prema bilo kojem od zahtjeva 1-10, naznačen time da je A fenil.
14. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time da je A supstituiran halogenom.
15. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time da je R3 C1-6alkoksi, C1-6halogenalkil ili halogen.
16. Spoj prema zahtjevu 15, naznačen time da je R3 metoksi ili etoksi.
17. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time da je X -CH2-.
18. Spoj prema bilo kojem od zahtjeva 1-16, naznačen time da je X -NH-.
19. Spoj prema zahtjevu 12, naznačen time da je A 4-(3,5-dikloropiridil).
20. Spoj prema bilo kojem od prethodnih zahtjeva, naznačen time da je R4 hidrogen.
21. Spoj prema bilo kojem od prethodnih zahtjeva, odabran is skupine koju sačinjavaju 2-(3,5-Dikloropiridin-4-il)-1-(7-metoksi-2’,3’,5’,6’-tetrahidro-spiro[1,3-benzodioksol-2,4’-(4H)-piran]-4-il)etanon (spoj 101), N-(3,5-Dikloropiridin-4-il)-7-metoksi-2’,3’,5’,6’-tetrahidro-spiro[1,3-benzodioksol-2,4’-(4H)-piran]-4-karboksamid (spoj 102), 2-(3,5-Dikloro-1-oksido-piridin-4-il)-1-(7-metoksi-2’,3’,5’,6’-tetrahidrospiro[1,3-benzodioksol-2,4’-(4H)-piran]-4-il)etanon (spoj 103), 2-(3,5-Dikloropiridin-4-il)-1-(7-metoksi-4’,5’-dihidro-spiro[1,3-benzodioksol-2,3’-(2H)-tiofen]-4-il)etanon (spoj 104), 2-(3,5-Dikloropiridin-4-il)-1-(7-metoksi-spiro[1,3-benzodioksol-2,4’-piperidin]-4-il)etanon (spoj 105), 2-(3,5-Dikloropiridin-4-il)-1-(7-metoksi-1’-[metoksikarbonil]-spiro[1,3-benzodioksol-2,4’-piperidin]-4-il)etanon (spoj 106), 2-(3,5-Dikloropiridin-4-il)-1-(7-metoksi-1’-[metilsulfonil]-spiro[1,3-benzodioksol-2,4’-piperidin]-4-il)etanon (spoj 107), 2-(3,5-Dikloropiridin-4-il)-1-(7-metoksi-1’-acetil-spiro[1,3-benzodioksol-2,4’-piperidin]-4-il)etanon (spoj 108) 2-(3,5-Dikloropiridin-4-il)-1-(7-metoksi-1’-metil-spiro[1,5-benzodioksol-2,4’-piperidin]-4-il)etanon (spoj 109), 2-(3,5-Dikloropiridin-4-il)-1-(7-metoksi-2’,3’,5’,6’-tetrahidro-spiro[1,3-benzodioksol-2,4’-(4H)-tiopiran]-4-il)etanon (spoj 110), 2-(3,5-Dikloropiridin-4-il)-1-(7-metoksi-2’,3’,5’,6’-tetrahidro-spiro[1,3-benzodioksol-2, 4’-(4H)-tiopiran 1’-oksid]-4-il)etanon. (spoj 111), 2-(3,5-Dikloropiridin-4-il)-1-(7-metoksi-2’,3’,5’,6’-tetrahidro-spiro[1,3-benzodioksol-2, 4’-(4H)-tiopiran-1’,1’-dioksid]-4-il)etanon (spoj 112), 2-(3,5-Dikloro-1-oksido-piridin-4-il)-1-(7-metoksi-2’,3’,5’,6’-tetrahidrospiro[1,3-benzodioksol-2,4’-(4H)-tiopiran-1’,1’-dioksid]-4-il)etanon (spoj 113), 2-(3-bromopiridin-4-il)-1-(7-metoksi-2’,3’,5’,6’-tetrahidro-spiro[1,3-benzodioksol-2, 4 ’-(4H)-tiopiran]-4-il)etanon (spoj 114), 2-(3-Bromo-pirazin-2-il))-1-(7-metoksi-2’,3’,5’,6’-tetrahidro-spiro[1,3-benzodioksol-2, 4’-(4H)-tiopiran]-4-il)etanon (spoj 115), 2-(-pirazin-2-il)-1-(7-metoksi-2’,3’,5’,6’-tetrahidro-spiro[1,3-benzodioksol-2, 4’-(4H)-tiopiran]-4-il)etanon (spoj 116), 2-(-piridin-4-il-)-1-(7-metoksi-2’,3’,5’,6’-tetrahidro-spiro[1,3-benzo-dioksol-2, 4’-(4H)-tiopiran]-4-il)etanon (spoj 117), 2-(kvinolin-4-il-)-1-(7-metoksi-2’,3’,5’,6’-tetrahidro-spiro[1,3-benzo-dioksol-2, 4’-(4H)-tiopiran]-4-il)etanon (spoj 118), 2-(2,6-Dikloro-fenil)-1-(7-metoksi-2’,3’,5’,6’-tetrahidro-spiro[1,3-benzodioksol-2, 4’-(4H)-tiopiran]-4-il)etanon (spoj 119), 2-(2-Kloro-fenil)-1-(7-metoksi-2’,3’,5’,6’-tetrahidro-spiro[1,3-benzodioksol-2, 4’-(4H)-tiopiran]-4-il)etanon (spoj 120), 2-(3,5-Dikloropiridin-4-il)-1-{9-metoksi-spiro[2H-1,5-benzodioksepin-3(4H),3’-oksetan]-6-il}etanon (spoj 121), 2-(3,5-Dikloro-1-oksido-piridin-4-il)-1-{9-metoksi-spiro[2H-1,5-benzodioksepin-3(4H),3’-oksetan]-6-il}etanon (spoj 122), 2-(3,5-Dikloropiridin-4-il)-1-{9-metoksi-spiro[2H-1,5-benzodioksepin-3(4H),3’-tietan]-6-il}etanon (spoj 123), 2-(3,5-Dikloropiridin-4-il)-1-{9-metoksi-spiro[2H-1,5-benzodioksepin-3(4H),3’-tietan-1’,1’-dioksid]-6-il}etanon (spoj 124), 2-(3,5-Dikloropiridin-1-oksido-4-il)-1-{9-metoksi-spiro[2H-1,5-benzodioksepin-3(4H),3’-tietan-1’,1’-dioksid]-6-il}etanon (spoj 125), 2-(3,5-Dikloropiridin-4-il)-1-{9-metoksi-spiro[2H-1,5-benzodioksepin-3(4H),2’-(1,3-dioksolan)]-6-il}etanon (spoj 126), 2-(3,5-Dikloropiridin-4-il)-1-{9-metoksi-spiro[2H-1,5-benzodioksepin-3(4H),4’-tetrahidropiran]-6-il}etanon (spoj 127), 2-(3,5-Dikloro-1-oksido-piridin-4-il)-1-{9-metoksi-spiro[2H-1,5-benzodioksepin-3(4H),4’-tetrahidropiran]-6-il}etanon (spoj 128), 2-(3,5-Dikloropiridin-4-il)-1-{9-metoksi-2’,2’-dimetil-spiro[2H-1,5-benzodioksepin-3(4H),5’-[1,3]dioksan]-6-il} etanon (spoj 129), 2-(3,5-Dikloropiridin-4-il)-1-{9-metoksi-spiro[2H-1,5-benzodioksepin-3(4H),5’-[1,3]dioksan]-6-il}etanon (spoj 130), 2-(3,5-Dikloro-1-oksido-piridin-4-il)-1-{9-metoksi-spiro[2H-1,5-benzodioksepin-3(4H),5’-[1,3]dioksan]-6-il}etanon (spoj 131), i 2-(3,5-Dikloropiridin-4-il)-1-{9-metoksi-spiro[2H-1,5-benzodioksepin-3(4H),5’-[1,3]ditian]-6-il}etanon (spoj 132), i njihove farmaceutski prihvatljive soli, hidrati, N-oksidi ili solvati.
22. Spoj prema bilo kojem od zahtjeva 1-21 za primjenu u liječenju.
23. Farmaceutski pripravak koji sadrži neki spoj prema bilo kojem od zahtjeva 1-21 zajedno s nekom farmaceutski prihvatljivom pomoćnom tvari ili prijenosnim sredstvom ili farmaceutski prihvatljivim nositelj(ima).
24. Farmaceutski pripravak prema zahtjevu 23 zajedno s jednim ili više drugih terapeutski djelatnih spojeva.
25. Spoj prema bilo kojem od zahtjeva 1-21 za primjenu u prevenciji, liječenju ili ublažavanju kožnih oboljenja ili stanja, ili akutnih ili kroničnih poremećaja kod rana na koži.
26. Spoj prema zahtjevu 25, za primjenu u prevenciji, liječenju ili ublažavanju kožnih oboljenja ili stanja odabranih iz skupine koju sačinjavaju proliferativni i upalni poremećaji na koži, psorijaza, rak, epidermalna upala, alopecija, atrofija kože, atrofija kože inducirana steroidima, starenje kože, foto starenje kože, akne, dermatitis, atopijski dermatitis, seboroični dermatitis, kontaktni dermatitis, urtikarija, svrbež i ekcem.
HRP20140585AT 2007-02-28 2014-06-23 Inovativni inhibitori fosfodiesteraze HRP20140585T1 (hr)

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US90384907P 2007-02-28 2007-02-28
US94684907P 2007-06-28 2007-06-28
PCT/DK2008/000080 WO2008104175A2 (en) 2007-02-28 2008-02-26 Novel phosphodiesterase inhibitors

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AU (1) AU2008221121B2 (hr)
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IL (1) IL200153A (hr)
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