HRP20231663T1 - Biciklički derivati heteroarila - Google Patents
Biciklički derivati heteroarila Download PDFInfo
- Publication number
- HRP20231663T1 HRP20231663T1 HRP20231663TT HRP20231663T HRP20231663T1 HR P20231663 T1 HRP20231663 T1 HR P20231663T1 HR P20231663T T HRP20231663T T HR P20231663TT HR P20231663 T HRP20231663 T HR P20231663T HR P20231663 T1 HRP20231663 T1 HR P20231663T1
- Authority
- HR
- Croatia
- Prior art keywords
- amine
- triazolo
- azabicyclo
- oxazepin
- tetrahydro
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims 22
- RETFIEPIZUQCDL-UHFFFAOYSA-N oxazin-2-amine Chemical compound NN1OC=CC=C1 RETFIEPIZUQCDL-UHFFFAOYSA-N 0.000 claims 10
- 229910052736 halogen Inorganic materials 0.000 claims 8
- 150000002367 halogens Chemical group 0.000 claims 8
- 125000000217 alkyl group Chemical group 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 6
- 239000001257 hydrogen Substances 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- PUVJNVLOUNIHNF-MFGZZSJASA-N CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C4=CC(Cl)=CC(F)=C4)C3=N2)=CN=N1 Chemical compound CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C4=CC(Cl)=CC(F)=C4)C3=N2)=CN=N1 PUVJNVLOUNIHNF-MFGZZSJASA-N 0.000 claims 2
- FECROEMXGDFEFX-MFGZZSJASA-N CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C4=CC(Cl)=CC(F)=C4)C3=N2)=NC=N1 Chemical compound CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C4=CC(Cl)=CC(F)=C4)C3=N2)=NC=N1 FECROEMXGDFEFX-MFGZZSJASA-N 0.000 claims 2
- PUVJNVLOUNIHNF-MVGGYSAASA-N CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C4=CC(Cl)=CC(F)=C4)C3=N2)=CN=N1 Chemical compound CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C4=CC(Cl)=CC(F)=C4)C3=N2)=CN=N1 PUVJNVLOUNIHNF-MVGGYSAASA-N 0.000 claims 2
- FECROEMXGDFEFX-MVGGYSAASA-N CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C4=CC(Cl)=CC(F)=C4)C3=N2)=NC=N1 Chemical compound CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C4=CC(Cl)=CC(F)=C4)C3=N2)=NC=N1 FECROEMXGDFEFX-MVGGYSAASA-N 0.000 claims 2
- DRMLDDBQPBECRA-GHEUYMLLSA-N COC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C4=CC(Cl)=CC(F)=C4)C3=N2)=CN=N1 Chemical compound COC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C4=CC(Cl)=CC(F)=C4)C3=N2)=CN=N1 DRMLDDBQPBECRA-GHEUYMLLSA-N 0.000 claims 2
- DRMLDDBQPBECRA-DIMRZHFKSA-N COC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C4=CC(Cl)=CC(F)=C4)C3=N2)=CN=N1 Chemical compound COC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C4=CC(Cl)=CC(F)=C4)C3=N2)=CN=N1 DRMLDDBQPBECRA-DIMRZHFKSA-N 0.000 claims 2
- QFLMYOYPGVRLER-UISQCYCNSA-N COC1=NC=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C4=CC(Cl)=CC(F)=C4)C3=N2)=C1 Chemical compound COC1=NC=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C4=CC(Cl)=CC(F)=C4)C3=N2)=C1 QFLMYOYPGVRLER-UISQCYCNSA-N 0.000 claims 2
- QFLMYOYPGVRLER-GUNXFRPYSA-N COC1=NC=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C4=CC(Cl)=CC(F)=C4)C3=N2)=C1 Chemical compound COC1=NC=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C4=CC(Cl)=CC(F)=C4)C3=N2)=C1 QFLMYOYPGVRLER-GUNXFRPYSA-N 0.000 claims 2
- 208000005145 Cerebral amyloid angiopathy Diseases 0.000 claims 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 229910052801 chlorine Chemical group 0.000 claims 2
- 239000000460 chlorine Chemical group 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- OUMFVKNEDMFGII-GHEUYMLLSA-N (8R)-8-(3-chloro-5-fluorophenyl)-N-[(1R,5S)-3-(2-methoxypyridin-4-yl)-3-azabicyclo[3.2.1]octan-8-yl]-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazin-2-amine Chemical compound ClC=1C=C(C=C(C=1)F)[C@H]1OCCN2C1=NC(=N2)NC1[C@H]2CN(C[C@@H]1CC2)C1=CC(=NC=C1)OC OUMFVKNEDMFGII-GHEUYMLLSA-N 0.000 claims 1
- SSQYSSOQTRMADE-REAHPQQBSA-N (8R)-8-(3-chloro-5-fluorophenyl)-N-[(1R,5S)-3-(6-methoxypyridazin-4-yl)-3-azabicyclo[3.2.1]octan-8-yl]-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazin-2-amine Chemical compound ClC=1C=C(C=C(C=1)F)[C@H]1OCCN2C1=NC(=N2)NC1[C@H]2CN(C[C@@H]1CC2)C1=CN=NC(=C1)OC SSQYSSOQTRMADE-REAHPQQBSA-N 0.000 claims 1
- DMNYTRIALSCYSN-VUBXYBDHSA-N (8R)-8-(3-chloro-5-fluorophenyl)-N-[(1R,5S)-3-(6-methylpyrimidin-4-yl)-3-azabicyclo[3.2.1]octan-8-yl]-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazin-2-amine Chemical compound ClC=1C=C(C=C(C=1)F)[C@H]1OCCN2C1=NC(=N2)NC1[C@H]2CN(C[C@@H]1CC2)C1=NC=NC(=C1)C DMNYTRIALSCYSN-VUBXYBDHSA-N 0.000 claims 1
- OUMFVKNEDMFGII-DIMRZHFKSA-N (8S)-8-(3-chloro-5-fluorophenyl)-N-[(1R,5S)-3-(2-methoxypyridin-4-yl)-3-azabicyclo[3.2.1]octan-8-yl]-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazin-2-amine Chemical compound ClC=1C=C(C=C(C=1)F)[C@@H]1OCCN2C1=NC(=N2)NC1[C@H]2CN(C[C@@H]1CC2)C1=CC(=NC=C1)OC OUMFVKNEDMFGII-DIMRZHFKSA-N 0.000 claims 1
- SSQYSSOQTRMADE-RJNPCAAESA-N (8S)-8-(3-chloro-5-fluorophenyl)-N-[(1R,5S)-3-(6-methoxypyridazin-4-yl)-3-azabicyclo[3.2.1]octan-8-yl]-6,8-dihydro-5H-[1,2,4]triazolo[5,1-c][1,4]oxazin-2-amine Chemical compound ClC=1C=C(C=C(C=1)F)[C@@H]1OCCN2C1=NC(=N2)NC1[C@H]2CN(C[C@@H]1CC2)C1=CN=NC(=C1)OC SSQYSSOQTRMADE-RJNPCAAESA-N 0.000 claims 1
- 208000018282 ACys amyloidosis Diseases 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- TZHWRCJKZZSICY-MFGZZSJASA-N CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C(C=CC(F)=C4)=C4F)C3=N2)=NC=N1 Chemical compound CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C(C=CC(F)=C4)=C4F)C3=N2)=NC=N1 TZHWRCJKZZSICY-MFGZZSJASA-N 0.000 claims 1
- SLOCFYCPEIIVMG-MFGZZSJASA-N CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C(C=CC=C4F)=C4F)C3=N2)=NC=N1 Chemical compound CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C(C=CC=C4F)=C4F)C3=N2)=NC=N1 SLOCFYCPEIIVMG-MFGZZSJASA-N 0.000 claims 1
- WXBDNKUJROQEHZ-MFGZZSJASA-N CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C4=CC(F)=CC(F)=C4)C3=N2)=NC=N1 Chemical compound CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C4=CC(F)=CC(F)=C4)C3=N2)=NC=N1 WXBDNKUJROQEHZ-MFGZZSJASA-N 0.000 claims 1
- TZHWRCJKZZSICY-MVGGYSAASA-N CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C(C=CC(F)=C4)=C4F)C3=N2)=NC=N1 Chemical compound CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C(C=CC(F)=C4)=C4F)C3=N2)=NC=N1 TZHWRCJKZZSICY-MVGGYSAASA-N 0.000 claims 1
- SLOCFYCPEIIVMG-MVGGYSAASA-N CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C(C=CC=C4F)=C4F)C3=N2)=NC=N1 Chemical compound CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C(C=CC=C4F)=C4F)C3=N2)=NC=N1 SLOCFYCPEIIVMG-MVGGYSAASA-N 0.000 claims 1
- WXBDNKUJROQEHZ-MVGGYSAASA-N CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C4=CC(F)=CC(F)=C4)C3=N2)=NC=N1 Chemical compound CC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C4=CC(F)=CC(F)=C4)C3=N2)=NC=N1 WXBDNKUJROQEHZ-MVGGYSAASA-N 0.000 claims 1
- KQQKMJRXNXRLPN-GHEUYMLLSA-N COC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C(C=CC(F)=C4)=C4F)C3=N2)=CN=N1 Chemical compound COC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C(C=CC(F)=C4)=C4F)C3=N2)=CN=N1 KQQKMJRXNXRLPN-GHEUYMLLSA-N 0.000 claims 1
- WLZZOJITXAXCRJ-GHEUYMLLSA-N COC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C(C=CC=C4F)=C4F)C3=N2)=CN=N1 Chemical compound COC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C(C=CC=C4F)=C4F)C3=N2)=CN=N1 WLZZOJITXAXCRJ-GHEUYMLLSA-N 0.000 claims 1
- WGNAEOBGKQHHBW-GHEUYMLLSA-N COC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C4=CC(F)=CC(F)=C4)C3=N2)=CN=N1 Chemical compound COC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@@H]3C4=CC(F)=CC(F)=C4)C3=N2)=CN=N1 WGNAEOBGKQHHBW-GHEUYMLLSA-N 0.000 claims 1
- KQQKMJRXNXRLPN-DIMRZHFKSA-N COC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C(C=CC(F)=C4)=C4F)C3=N2)=CN=N1 Chemical compound COC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C(C=CC(F)=C4)=C4F)C3=N2)=CN=N1 KQQKMJRXNXRLPN-DIMRZHFKSA-N 0.000 claims 1
- WLZZOJITXAXCRJ-DIMRZHFKSA-N COC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C(C=CC=C4F)=C4F)C3=N2)=CN=N1 Chemical compound COC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C(C=CC=C4F)=C4F)C3=N2)=CN=N1 WLZZOJITXAXCRJ-DIMRZHFKSA-N 0.000 claims 1
- WGNAEOBGKQHHBW-DIMRZHFKSA-N COC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C4=CC(F)=CC(F)=C4)C3=N2)=CN=N1 Chemical compound COC1=CC(N(C[C@H]2CC3)C[C@H]3C2NC2=NN(CCCO[C@H]3C4=CC(F)=CC(F)=C4)C3=N2)=CN=N1 WGNAEOBGKQHHBW-DIMRZHFKSA-N 0.000 claims 1
- DMNYTRIALSCYSN-VCTRGTQWSA-N ClC=1C=C(C=C(C1)F)[C@@H]1OCCN2C1=NC(=N2)NC2[C@H]1CN(C[C@@H]2CC1)C1=NC=NC(=C1)C Chemical compound ClC=1C=C(C=C(C1)F)[C@@H]1OCCN2C1=NC(=N2)NC2[C@H]1CN(C[C@@H]2CC1)C1=NC=NC(=C1)C DMNYTRIALSCYSN-VCTRGTQWSA-N 0.000 claims 1
- 201000010374 Down Syndrome Diseases 0.000 claims 1
- 208000007487 Familial Cerebral Amyloid Angiopathy Diseases 0.000 claims 1
- 208000032849 Hereditary cerebral hemorrhage with amyloidosis Diseases 0.000 claims 1
- 208000005314 Multi-Infarct Dementia Diseases 0.000 claims 1
- 206010044688 Trisomy 21 Diseases 0.000 claims 1
- 201000004810 Vascular dementia Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 229940125898 compound 5 Drugs 0.000 claims 1
- 208000017004 dementia pugilistica Diseases 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
-
- 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
- A61P35/00—Antineoplastic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Claims (16)
1. Spoj, naznačen time, da je predstavljen formulom (I)
[image]
pri čemu
R1 je halogen, C1-7 alkil, C1-7 alkil supstituiran halogenom, C1-7 alkoksi, ili C1-7 alkoksi supstituiran halogenom,
i R1 može biti različit ako je n = 2 ili 3;
m je 1 ili 2;
n je 1, 2 ili 3;
Ar je šesteročlana heteroarilna skupina, koja se bira između
[image]
,
[image]
,
[image]
pri čemu
R2 je vodik, halogen, C1−7 alkil, C1−7 alkil supstituiran halogenom, ili C1−7 alkoksi;
R3 je vodik ili halogen;
ili njegova farmaceutski prihvatljiva sol.
2. Spoj koji ima formulu (I) prema patentnom zahtjevu 1, naznačen time, da je spoj koji ima formulu (I) spoj predstavljen formulom (Ia):
[image]
pri čemu su R1, m, n i Ar definirani kao u patentnom zahtjevu 1.
3. Spoj koji ima formulu (I) prema patentnom zahtjevu 1, naznačen time, da je spoj koji ima formulu (I) spoj predstavljen formulom (Ib):
[image]
pri čemu su R1, m, n i Ar definirani kao u patentnom zahtjevu 1.
4. Spoj koji ima formulu (I) prema bilo kojem od patentnih zahtjeva 1 do 3, naznačen time, da R1 je halogen.
5. Spoj koji ima formulu (I) prema bilo kojem od patentnih zahtjeva 1 do 4, naznačen time, da R1 je fluor ili klor.
6. Spoj koji ima formulu (I) prema bilo kojem od patentnih zahtjeva od 1 do 5, naznačen time, da n je 2 ili 3.
7. Spoj koji ima formulu (I) prema bilo kojem od patentnih zahtjeva 1 do 6, naznačen time, da Ar je šesteročlana heteroarilna skupina, koja se bira između
[image]
,
[image]
,
[image]
pri čemu
R2 je C1-7 alkil ili C1-7 alkoksi;
R3 je vodik.
8. Spoj koji ima formulu (I) prema bilo kojem od patentnih zahtjeva 1 do 7, naznačen time, da Ar je šesteročlana heteroarilna skupina, koja se bira između
[image]
,
[image]
,
[image]
pri čemu
R2 je metil ili metoksi;
R3 je vodik.
9. Spoj koji ima formulu (I) prema bilo kojem od patentnih zahtjeva od 1 do 3, naznačen time, da:
R1 je halogen;
m je 1 ili 2;
n je 2 ili 3;
Ar je šesteročlana heteroarilna skupina, koja se bira između
[image]
,
[image]
,
[image]
pri čemu
R2 je C1-7 alkil ili C1-7 alkoksi;
R3 je vodik.
10. Spoj koji ima formulu (I) prema bilo kojem od patentnih zahtjeva od 1 do 3, naznačen time, da:
R1 je fluor ili klor,
m je 1 ili 2;
n je 2 ili 3;
Ar je šesteročlana heteroarilna skupina, koja se bira između
[image]
,
[image]
,
[image]
pri čemu
R2 je metil ili metoksi;
R3 je vodik.
11. Spoj prema bilo kojem od patentnih zahtjeva 1 do 10, naznačen time, da je odabran iz skupine koju čine
(9R)-9-(2,3-difluorofenil)-N-[(1R,5S)-3-(6-metoksipiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-9-(2,3-difluorofenil)-N-[(1R,5S)-3-(6-metoksipiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9R)-9-(2,4-difluorofenil)-N-[(1R,5S)-3-(6-metoksipiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-9-(2,4-difluorofenil)-N-[(1R,5S)-3-(6-metoksipiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9R)-9-(2,3-difluorofenil)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-9-(2,3-difluorofenil)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9R)-9-(3,5-difluorofenil)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-9-(3,5-difluorofenil)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9R)-9-(2,4-difluorofenil)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-9-(2,4-difluorofenil)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9R)-9-(3,5-difluorofenil)-N-[(1R,5S)-3-(6-metoksipiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-9-(3,5-difluorofenil)-N-[(1R,5S)-3-(6-metoksipiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9R)-N-[(1R,5S)-3-(6-metoksipiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-9-(2,3,4-trifluorofenil)-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-N-[(1R,5S)-3-(6-metoksipiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-9-(2,3,4-trifluorofenil)-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9R)-9-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(6-metilpiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-9-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(6-metilpiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9R)-N-[(1R,5S)-3-(6-metilpiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-9-(2,3,4-trifluorofenil)-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-N-[(1R,5S)-3-(6-metilpiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-9-(2,3,4-trifluorofenil)-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9R)-9-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(6-metoksipiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8 -il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-9-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(6-metoksipiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8 -il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(8R)-8-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(6-metoksipiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8 -il]-6,8-dihidro-5H-[1,2,4]triazolo[5,1-c][1,4]oksazin-2-amin;
(8S)-8-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(6-metoksipiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8 -il]-6,8-dihidro-5H-[1,2,4]triazolo[5,1-c][1,4]oksazin-2-amin;
(8R)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-8-(2,3,4-trifluorofenil)-6,8-dihidro-5H-[1,2,4]triazolo[5,1-c][1,4]oksazin-2-amin;
(8S)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-8-(2,3,4-trifluorofenil)-6,8-dihidro-5H-[1,2,4]triazolo[5,1-c][1,4]oksazin-2-amin;
(8R)-8-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8 -il]-6,8-dihidro-5H-[1,2,4]triazolo[5,1-c][1,4]oksazin-2-amin;
(8S)-8-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8 -il]-6,8-dihidro-5H-[1,2,4]triazolo[5,1-c][1,4]oksazin-2-amin;
(8R)-N-[(1R,5S)-3-(6-metoksipiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-8-(2,3,4-trifluorofenil)-6,8-dihidro-5H-[1,2,4]triazolo[5,1-c][1,4]oksazin-2-amin;
(8S)-N-[(1R,5S)-3-(6-metoksipiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-8-(2,3,4-trifluorofenil)-6,8-dihidro-5H-[1,2,4]triazolo[5,1-c][1,4]oksazin-2-amin;
(8R)-8-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(2-metoksi-4-piridil)-3-azabiciklo[3.2.1]oktan-8 -il]-6,8-dihidro-5H-[1,2,4]triazolo[5,1-c][1,4]oksazin-2-amin;
(8S)-8-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(2-metoksi-4-piridil)-3-azabiciklo[3.2.1]oktan-8 -il]-6,8-dihidro-5H-[1,2,4]triazolo[5,1-c][1,4]oksazin-2-amin;
(8R)-N-[(1R,5S)-3-(2-metoksi-4-piridil)-3-azabiciklo[3.2.1]oktan-8-il]-8-(2,3,4-trifluorofenil)-6,8-dihidro-5H-[1,2,4]triazolo[5,1-c][1,4]oksazin-2-amin;
(8S)-N-[(1R,5S)-3-(2-metoksi-4-piridil)-3-azabiciklo[3.2.1]oktan-8-il]-8-(2,3,4-trifluorofenil)-6,8-dihidro-5H-[1,2,4]triazolo[5,1-c][1,4]oksazin-2-amin;
(9R)-9-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-9-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9R)-9-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(2-metoksi-4-piridil)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-9-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(2-metoksi-4-piridil)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9R)-N-[(1R,5S)-3-(2-metoksi-4-piridil)-3-azabiciklo[3.2.1]oktan-8-il]-9-(2,3,4-trifluorofenil)-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-N-[(1R,5S)-3-(2-metoksi-4-piridil)-3-azabiciklo[3.2.1]oktan-8-il]-9-(2,3,4-trifluorofenil)-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9R)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-9-(2,3,4-trifluorofenil)-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-9-(2,3,4-trifluorofenil)-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
ili njihova farmaceutski prihvatljiva sol.
12. Spoj prema bilo kojem od patentnih zahtjeva 1 do 10, naznačen time, da je odabran iz skupine koju čine
(9R)-N-[(1R,5S)-3-(6-metoksipiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-9-(2,3,4-trifluorofenil)-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-N-[(1R,5S)-3-(6-metoksipiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-9-(2,3,4-trifluorofenil)-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9R)-9-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(6-metilpiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-9-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(6-metilpiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9R)-N-[(1R,5S)-3-(6-metilpiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-9-(2,3,4-trifluorofenil)-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-N-[(1R,5S)-3-(6-metilpiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-9-(2,3,4-trifluorofenil)-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9R)-9-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(6-metoksipiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8 -il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-9-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(6-metoksipiridazin-4-il)-3-azabiciklo[3.2.1]oktan-8 -il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(8R)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-8-(2,3,4-trifluorofenil)-6,8-dihidro-5H-[1,2,4]triazolo[5,1-c][1,4]oksazin-2-amin;
(8S)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-8-(2,3,4-trifluorofenil)-6,8-dihidro-5H-[1,2,4]triazolo[5,1-c][1,4]oksazin-2-amin;
(8R)-N-[(1R,5S)-3-(2-metoksi-4-piridil)-3-azabiciklo[3.2.1]oktan-8-il]-8-(2,3,4-trifluorofenil)-6,8-dihidro-5H-[1,2,4]triazolo[5,1-c][1,4]oksazin-2-amin;
(8S)-N-[(1R,5S)-3-(2-metoksi-4-piridil)-3-azabiciklo[3.2.1]oktan-8-il]-8-(2,3,4-trifluorofenil)-6,8-dihidro-5H-[1,2,4]triazolo[5,1-c][1,4]oksazin-2-amin;
(9R)-9-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-9-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9R)-9-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(2-metoksi-4-piridil)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-9-(3-kloro-5-fluoro-fenil)-N-[(1R,5S)-3-(2-metoksi-4-piridil)-3-azabiciklo[3.2.1]oktan-8-il]-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9R)-N-[(1R,5S)-3-(2-metoksi-4-piridil)-3-azabiciklo[3.2.1]oktan-8-il]-9-(2,3,4-trifluorofenil)-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-N-[(1R,5S)-3-(2-metoksi-4-piridil)-3-azabiciklo[3.2.1]oktan-8-il]-9-(2,3,4-trifluorofenil)-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9R)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-9-(2,3,4-trifluorofenil)-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
(9S)-N-[(1R,5S)-3-(6-metilpirimidin-4-il)-3-azabiciklo[3.2.1]oktan-8-il]-9-(2,3,4-trifluorofenil)-5,6,7,9-tetrahidro-[1,2,4]triazolo[5,1-c][1,4]oksazepin-2-amin;
ili njihova farmaceutski prihvatljiva sol.
13. Postupak za pripravu spoja prema bilo kojem od patentnih zahtjeva 1 do 12, naznačen time, da obuhvaća reakciju između spoja 5
[image]
i amina 6
[image]
pri čemu su Ar, R1, n i m definirani kao u bilo kojem od patentnih zahtjeva 1 do 12, kako bi se dobio navedeni spoj koji ima formulu (I), i po želji, pretvaranje dobivenih spojeva u njihovu farmaceutski prihvatljivu sol.
14. Spoj prema bilo kojem od patentnih zahtjeva 1 do 12, naznačen time, da se primjenjuje kao terapeutski aktivna tvar.
15. Farmaceutski pripravak, naznačen time, da sadrži spoj prema bilo kojem od patentnih zahtjeva 1 do 12 i terapeutski inertni nosač.
16. Spoj prema bilo kojem od patentnih zahtjeva 1 do 12, naznačen time, da se primjenjuje u terapijskom i/ili profilaktičkom liječenju Alzheimerove bolesti, cerebralne amiloidne angiopatije, nasljednog moždanog krvarenja s amiloidozom Dutch tipa, multiinfarktne demencije, poremećaja dementia pugilistica ili Downovog sindroma.
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