HRP20151250T1 - Derivati izoksazolo-piridina - Google Patents
Derivati izoksazolo-piridina Download PDFInfo
- Publication number
- HRP20151250T1 HRP20151250T1 HRP20151250TT HRP20151250T HRP20151250T1 HR P20151250 T1 HRP20151250 T1 HR P20151250T1 HR P20151250T T HRP20151250T T HR P20151250TT HR P20151250 T HRP20151250 T HR P20151250T HR P20151250 T1 HRP20151250 T1 HR P20151250T1
- Authority
- HR
- Croatia
- Prior art keywords
- compound according
- methyl
- compound
- phenyl
- optionally substituted
- Prior art date
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- NABZXASCLFSKLF-UHFFFAOYSA-N [1,2]oxazolo[4,3-b]pyridine Chemical class C1=CC=NC2=CON=C21 NABZXASCLFSKLF-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 14
- -1 benzyloxy, tetrahydropyridinyl Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 4
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 3
- 229940079593 drug Drugs 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 229920006395 saturated elastomer Polymers 0.000 claims 3
- NDOVLWQBFFJETK-UHFFFAOYSA-N 1,4-thiazinane 1,1-dioxide Chemical compound O=S1(=O)CCNCC1 NDOVLWQBFFJETK-UHFFFAOYSA-N 0.000 claims 2
- DBPRZHYSXRZSHX-UHFFFAOYSA-N 6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridine-3-carboxylic acid Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC1=CC=C(C(O)=O)C=N1 DBPRZHYSXRZSHX-UHFFFAOYSA-N 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 230000001149 cognitive effect Effects 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- 125000004043 oxo group Chemical group O=* 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
-
- 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
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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
- C07D491/08—Bridged systems
-
- 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
Claims (14)
1. Spoj, naznačen time, da ima formulu I:
[image]
u kojoj
X je O ili NH;
R1 je fenil, piridinil ili pirimidinil, od kojih je svaki po želji supstituiran s 1,2 ili 3 halogena;
R2 je H ili CH3 ili CF3;
R3 i R6 su H, halogen, CN ili C1-7-alkil;
R4 je -C(O)-NRbRc, gdje Rb i Rc zajedno s dušikom na kojega su vezani, tvore heterociklilni dio skupine, po želji supstituiran s jednim ili više A;
R5 je H, CF3, benziloksi, tetrahidropiridinil opcijski supstituiran s jednim metilom, -C(O)-NRbRc, pri čemu je svaki od Rb i Rc neovisno H ili morfolinil;
A je hidroksi, okso, C1-7-alkil, C1-7-alkoksi, C1-7-haloaIkil, C1-7-hidroksialkil, halogen ili CN;
pri čemu se izraz „heterociklilni dio skupine" odnosi na monovalentni zasićeni ili djelomično zasićeni 3-člani do 7-člani monociklički sustav prstena, ili 9-člani do 10-člani biciklički sustav prstena, gdje se jedan, dva, tri ili četiri atoma ugljika toga prstena, zamjenjuje s N, O ili S, i s točkom priključenja na zasićenom ili djelomično nezasićenom prstenu od navedenog sustava prstena; ili njegova farmaceutski prihvatljiva sol.
2. Spoj prema zahtjevu 1, naznačen time, da R2 je metil ili trifluorometil.
3. Spoj prema bilo kojem od zahtjeva 1 do 2, naznačen time, da R3 je H, CN ili metil.
4. Spoj prema bilo kojem od zahtjeva 1 do 3, naznačen time, da R6 je H, Br ili metil.
5. Spoj prema bilo kojem od zahtjeva 1 do 4, naznačen time, da je heterociklilni dio skupine od R4 odabran od sljedećih: morfolinil, tiomorfolinil, 5,6,7,8-tetrahidro-[1,2,4]triazolo-[4,3-a]pirazinil, i 4,5,6,7-tetrahidro-pirazolo [1,5-a]pirimidinil, od kojih je svaki po želji supstituiran s jednim ili više A.
6. Spoj prema bilo kojem od zahtjeva 1 do 5, naznačen time, da R5 je H ili CF3.
7. Spoj prema bilo kojem od zahtjeva 1 do 6, naznačen time, da R5 je H ili CF3, R3 i R5 su H, halogen, CN ili C1-7-alkil.
8. Spoj prema bilo kojem od zahtjeva 1 do 7, naznačen time, da spoj je (1,1-diokso-1λ6-tiomorfolin-4-il)-{6-[3-(4-fluoro-fenil)-5-metil-izoksazol-4-ilmetoksi]-piridin-3-il}-metanon.
9. Spoj prema zahtjevu 8, naznačen time, da se on može dobiti pomoću reakcije spoja 6-[3-(4-fluoro-fenil)-5-metil-izoksazol-4-ilmetoksi]-nikotinska kiselina s tiomorfolin-S,S-dioksidom.
10. Spoj prema zahtjevu 9, naznačen time, da se spojevi 2-(1H-benzotriazol-1-il)-1,1,3,3-tetrametiluronij-tetrafluoroborat i tiomorfolin-S,S-dioksid, dodaju u otopinu od 6-[3-(4-fluoro-fenil)-5-metil-izoksazol-4-ilmetoksi]-nikotinske kiseline u DMF.
11. Spoj prema bilo kojem od zahtjeva 1 do 10, naznačen time, da se upotrebljava kao lijek.
12. Lijek, naznačen time, da sadrži barem jedan spoj formule I prema bilo kojem od zahtjeva 1 do 10.
13. Lijek prema zahtjevu 12, naznačen time, da se upotrebljava u liječenju kognitivnih poremećaja ili kao kognitivni pobuđivač.
14. Lijek prema zahtjevu 13, naznačen time, da se upotrebljava u liječenju Alzheimerove bolesti.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07122240 | 2007-12-04 | ||
| EP14168581.8A EP2767536B1 (en) | 2007-12-04 | 2008-11-26 | Isoxazolo-pyridine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20151250T1 true HRP20151250T1 (hr) | 2015-12-18 |
Family
ID=40329314
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20150348TT HRP20150348T1 (hr) | 2007-12-04 | 2015-03-27 | Derivati izoksazolo-piridina |
| HRP20151250TT HRP20151250T1 (hr) | 2007-12-04 | 2015-11-20 | Derivati izoksazolo-piridina |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20150348TT HRP20150348T1 (hr) | 2007-12-04 | 2015-03-27 | Derivati izoksazolo-piridina |
Country Status (34)
| Country | Link |
|---|---|
| US (6) | US20090143371A1 (hr) |
| EP (2) | EP2227467B1 (hr) |
| JP (1) | JP5301557B2 (hr) |
| KR (2) | KR20120102117A (hr) |
| CN (1) | CN101889010B (hr) |
| AR (1) | AR069523A1 (hr) |
| AU (1) | AU2008333326B2 (hr) |
| BR (1) | BRPI0820112B8 (hr) |
| CA (1) | CA2707648C (hr) |
| CL (1) | CL2008003591A1 (hr) |
| CO (1) | CO6351788A2 (hr) |
| CR (1) | CR11454A (hr) |
| CY (2) | CY1116119T1 (hr) |
| DK (2) | DK2227467T3 (hr) |
| EC (1) | ECSP10010230A (hr) |
| ES (2) | ES2550994T3 (hr) |
| HK (1) | HK1149756A1 (hr) |
| HR (2) | HRP20150348T1 (hr) |
| HU (1) | HUE025545T2 (hr) |
| IL (1) | IL205759A (hr) |
| MA (1) | MA31865B1 (hr) |
| MX (1) | MX2010005717A (hr) |
| MY (1) | MY156747A (hr) |
| NZ (1) | NZ585308A (hr) |
| PE (2) | PE20130242A1 (hr) |
| PL (2) | PL2227467T3 (hr) |
| PT (2) | PT2767536E (hr) |
| RS (2) | RS53877B1 (hr) |
| RU (1) | RU2484091C2 (hr) |
| SI (2) | SI2767536T1 (hr) |
| TW (1) | TWI363624B (hr) |
| UA (1) | UA100132C2 (hr) |
| WO (1) | WO2009071476A1 (hr) |
| ZA (1) | ZA201003631B (hr) |
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|---|---|---|---|---|
| PL2227467T3 (pl) | 2007-12-04 | 2015-05-29 | Hoffmann La Roche | Pochodne izoksazolo-pirydyny |
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| PL2227467T3 (pl) | 2007-12-04 | 2015-05-29 | Hoffmann La Roche | Pochodne izoksazolo-pirydyny |
| CA2706990C (en) | 2007-12-04 | 2016-05-10 | F. Hoffmann-La Roche Ag | Isoxazolo-pyrazine derivatives |
| US20100280019A1 (en) * | 2009-04-30 | 2010-11-04 | Roland Jakob-Roetne | Isoxazoles |
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