HRP20100461T1 - Heteroaromatični spojevi hinolina i njihova uporaba kao pde10 inhibitora - Google Patents
Heteroaromatični spojevi hinolina i njihova uporaba kao pde10 inhibitora Download PDFInfo
- Publication number
- HRP20100461T1 HRP20100461T1 HR20100461T HRP20100461T HRP20100461T1 HR P20100461 T1 HRP20100461 T1 HR P20100461T1 HR 20100461 T HR20100461 T HR 20100461T HR P20100461 T HRP20100461 T HR P20100461T HR P20100461 T1 HRP20100461 T1 HR P20100461T1
- Authority
- HR
- Croatia
- Prior art keywords
- pyridin
- quinoline
- pyrazol
- methyl
- phenoxymethyl
- Prior art date
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- -1 Heteroaromatic quinoline compounds Chemical class 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 32
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 11
- 239000001257 hydrogen Substances 0.000 claims abstract 11
- 150000003839 salts Chemical class 0.000 claims abstract 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract 10
- 229910052799 carbon Inorganic materials 0.000 claims abstract 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract 9
- 150000002367 halogens Chemical class 0.000 claims abstract 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000003118 aryl group Chemical group 0.000 claims abstract 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 4
- 239000001301 oxygen Substances 0.000 claims abstract 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims abstract 3
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 3
- 125000004429 atom Chemical group 0.000 claims abstract 3
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims abstract 3
- 125000002950 monocyclic group Chemical class 0.000 claims abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract 2
- 125000001424 substituent group Chemical group 0.000 claims abstract 2
- 206010012289 Dementia Diseases 0.000 claims 6
- 208000028017 Psychotic disease Diseases 0.000 claims 6
- 230000004770 neurodegeneration Effects 0.000 claims 6
- 208000020401 Depressive disease Diseases 0.000 claims 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 208000024254 Delusional disease Diseases 0.000 claims 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- 208000024714 major depressive disease Diseases 0.000 claims 3
- 230000036651 mood Effects 0.000 claims 3
- 208000002851 paranoid schizophrenia Diseases 0.000 claims 3
- PRWFSBVVFNTTJQ-UHFFFAOYSA-N 2-[[4-(2-methyl-4-pyridin-4-ylpyrazol-3-yl)phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C=1N(C)N=CC=1C1=CC=NC=C1 PRWFSBVVFNTTJQ-UHFFFAOYSA-N 0.000 claims 2
- AZEXWHKOMMASPA-UHFFFAOYSA-N 2-{[4-(1-methyl-4-pyridin-4-yl-1h-pyrazol-3-yl)phenoxy]methyl}quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(C)C=C1C1=CC=NC=C1 AZEXWHKOMMASPA-UHFFFAOYSA-N 0.000 claims 2
- VRWJZGHUCOFGPZ-UHFFFAOYSA-N 2-{[4-(4-pyridin-4-yl-1h-pyrazol-3-yl)phenoxy]methyl}quinoline Chemical compound C=1C=C2C=CC=CC2=NC=1COC(C=C1)=CC=C1C1=NNC=C1C1=CC=NC=C1 VRWJZGHUCOFGPZ-UHFFFAOYSA-N 0.000 claims 2
- 206010065040 AIDS dementia complex Diseases 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000005314 Multi-Infarct Dementia Diseases 0.000 claims 2
- 208000008589 Obesity Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000006011 Stroke Diseases 0.000 claims 2
- 208000011963 Substance-induced psychotic disease Diseases 0.000 claims 2
- 231100000393 Substance-induced psychotic disorder Toxicity 0.000 claims 2
- 201000004810 Vascular dementia Diseases 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 206010007776 catatonia Diseases 0.000 claims 2
- 230000002490 cerebral effect Effects 0.000 claims 2
- ZPUCINDJVBIVPJ-LJISPDSOSA-N cocaine Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 235000020824 obesity Nutrition 0.000 claims 2
- 208000022821 personality disease Diseases 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 230000008733 trauma Effects 0.000 claims 2
- RUHAIMFLJXRIOR-LJQANCHMSA-N (2r)-1-[4-pyridin-4-yl-3-[4-(quinolin-2-ylmethoxy)phenyl]pyrazol-1-yl]propan-2-ol Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(C[C@H](O)C)C=C1C1=CC=NC=C1 RUHAIMFLJXRIOR-LJQANCHMSA-N 0.000 claims 1
- RUHAIMFLJXRIOR-IBGZPJMESA-N (2s)-1-[4-pyridin-4-yl-3-[4-(quinolin-2-ylmethoxy)phenyl]pyrazol-1-yl]propan-2-ol Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(C[C@@H](O)C)C=C1C1=CC=NC=C1 RUHAIMFLJXRIOR-IBGZPJMESA-N 0.000 claims 1
- KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims 1
- RUHAIMFLJXRIOR-UHFFFAOYSA-N 1-[4-pyridin-4-yl-3-[4-(quinolin-2-ylmethoxy)phenyl]pyrazol-1-yl]propan-2-ol Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(O)C)C=C1C1=CC=NC=C1 RUHAIMFLJXRIOR-UHFFFAOYSA-N 0.000 claims 1
- OMRQGOHJLIKRNJ-UHFFFAOYSA-N 1-[4-pyridin-4-yl-5-[4-(quinolin-2-ylmethoxy)phenyl]pyrazol-1-yl]propan-2-ol Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C=1N(CC(O)C)N=CC=1C1=CC=NC=C1 OMRQGOHJLIKRNJ-UHFFFAOYSA-N 0.000 claims 1
- JYFZUNQQRAJGHS-UHFFFAOYSA-N 2-[1-[4-(1-methyl-4-pyridin-4-ylpyrazol-3-yl)phenoxy]ethyl]quinoline Chemical compound C=1C=C2C=CC=CC2=NC=1C(C)OC(C=C1)=CC=C1C1=NN(C)C=C1C1=CC=NC=C1 JYFZUNQQRAJGHS-UHFFFAOYSA-N 0.000 claims 1
- QEDXQTGIBNYPTN-UHFFFAOYSA-N 2-[2-[4-(1-methyl-4-pyridin-4-ylpyrazol-3-yl)phenyl]ethyl]quinoline Chemical compound C=1C=C(CCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(C)C=C1C1=CC=NC=C1 QEDXQTGIBNYPTN-UHFFFAOYSA-N 0.000 claims 1
- FTOVUYIQDPEFAM-UHFFFAOYSA-N 2-[2-[4-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenyl]ethyl]quinoline Chemical compound C=1C=C2C=CC=CC2=NC=1CCC(C=C1)=CC=C1C=1NN=CC=1C1=CC=NC=C1 FTOVUYIQDPEFAM-UHFFFAOYSA-N 0.000 claims 1
- UJAGLBQVYJPDDQ-UHFFFAOYSA-N 2-[[2,3-difluoro-4-(1-methyl-4-pyridin-4-ylpyrazol-3-yl)phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C(F)=C(F)C=1C1=NN(C)C=C1C1=CC=NC=C1 UJAGLBQVYJPDDQ-UHFFFAOYSA-N 0.000 claims 1
- JUCIQNCMRHCEFW-UHFFFAOYSA-N 2-[[2-chloro-4-(1-methyl-4-pyridin-4-ylpyrazol-3-yl)phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C(Cl)=CC=1C1=NN(C)C=C1C1=CC=NC=C1 JUCIQNCMRHCEFW-UHFFFAOYSA-N 0.000 claims 1
- SODQNGJPEKNZBT-UHFFFAOYSA-N 2-[[2-chloro-4-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C(Cl)=CC=1C1=NNC=C1C1=CC=NC=C1 SODQNGJPEKNZBT-UHFFFAOYSA-N 0.000 claims 1
- OIUFHLZLDYGIKF-UHFFFAOYSA-N 2-[[2-fluoro-4-(1-methyl-4-pyridin-4-ylpyrazol-3-yl)phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C(F)=CC=1C1=NN(C)C=C1C1=CC=NC=C1 OIUFHLZLDYGIKF-UHFFFAOYSA-N 0.000 claims 1
- YOABOEUHOSBBNP-UHFFFAOYSA-N 2-[[2-fluoro-4-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C(F)=CC=1C1=NNC=C1C1=CC=NC=C1 YOABOEUHOSBBNP-UHFFFAOYSA-N 0.000 claims 1
- HFOVYIVZZFUCME-UHFFFAOYSA-N 2-[[3-fluoro-4-(1-methyl-4-pyridin-4-ylpyrazol-3-yl)phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=C(F)C=1C1=NN(C)C=C1C1=CC=NC=C1 HFOVYIVZZFUCME-UHFFFAOYSA-N 0.000 claims 1
- VXZDAYNHUOIVSC-UHFFFAOYSA-N 2-[[3-fluoro-4-(4-pyridin-4-yl-1h-pyrazol-5-yl)phenoxy]methyl]quinoline Chemical compound FC1=CC(OCC=2N=C3C=CC=CC3=CC=2)=CC=C1C1=NNC=C1C1=CC=NC=C1 VXZDAYNHUOIVSC-UHFFFAOYSA-N 0.000 claims 1
- DXDMXTCWTGFOSL-UHFFFAOYSA-N 2-[[3-fluoro-4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical compound FC1=CC(OCC=2N=C3C=CC=CC3=CC=2)=CC=C1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 DXDMXTCWTGFOSL-UHFFFAOYSA-N 0.000 claims 1
- XEDXYELVMICFBM-UHFFFAOYSA-N 2-[[4-(1,5-dimethyl-4-pyridin-4-ylpyrazol-3-yl)phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(C)C(C)=C1C1=CC=NC=C1 XEDXYELVMICFBM-UHFFFAOYSA-N 0.000 claims 1
- MSCSERRKBGIMGH-UHFFFAOYSA-N 2-[[4-(1-ethyl-4-pyridin-4-ylpyrazol-3-yl)phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC)C=C1C1=CC=NC=C1 MSCSERRKBGIMGH-UHFFFAOYSA-N 0.000 claims 1
- AESZYYCTKODVMP-UHFFFAOYSA-N 2-[[4-(1-methyl-3-pyridin-4-ylpyrazol-4-yl)phenoxy]methyl]quinoline Chemical compound N=1N(C)C=C(C=2C=CC(OCC=3N=C4C=CC=CC4=CC=3)=CC=2)C=1C1=CC=NC=C1 AESZYYCTKODVMP-UHFFFAOYSA-N 0.000 claims 1
- VBTLLMHNJNKKPI-UHFFFAOYSA-N 2-[[4-(1-methyl-4-pyridazin-4-ylpyrazol-3-yl)phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(C)C=C1C1=CC=NN=C1 VBTLLMHNJNKKPI-UHFFFAOYSA-N 0.000 claims 1
- NEZLZBNIWODXNN-UHFFFAOYSA-N 2-[[4-(1-methyl-5-pyridin-4-ylpyrazol-4-yl)phenoxy]methyl]quinoline Chemical compound CN1N=CC(C=2C=CC(OCC=3N=C4C=CC=CC4=CC=3)=CC=2)=C1C1=CC=NC=C1 NEZLZBNIWODXNN-UHFFFAOYSA-N 0.000 claims 1
- ZBVZRRRHCWSVNJ-UHFFFAOYSA-N 2-[[4-(1-propan-2-yl-4-pyridin-4-ylpyrazol-3-yl)phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(C(C)C)C=C1C1=CC=NC=C1 ZBVZRRRHCWSVNJ-UHFFFAOYSA-N 0.000 claims 1
- YEYYFESVOAQOMX-UHFFFAOYSA-N 2-[[4-(1-pyridin-4-ylimidazol-2-yl)phenoxy]methyl]quinoline Chemical compound C=1C=C2C=CC=CC2=NC=1COC(C=C1)=CC=C1C1=NC=CN1C1=CC=NC=C1 YEYYFESVOAQOMX-UHFFFAOYSA-N 0.000 claims 1
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- UFBIOSDYTOETCT-UHFFFAOYSA-N 2-[[4-(2-ethyl-4-pyridin-4-ylpyrazol-3-yl)phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C=1N(CC)N=CC=1C1=CC=NC=C1 UFBIOSDYTOETCT-UHFFFAOYSA-N 0.000 claims 1
- XLSBGYBUVUYTKT-UHFFFAOYSA-N 2-[[4-(2-ethyl-5-pyridin-4-ylimidazol-1-yl)phenoxy]methyl]quinoline Chemical compound C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1N1C(CC)=NC=C1C1=CC=NC=C1 XLSBGYBUVUYTKT-UHFFFAOYSA-N 0.000 claims 1
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- 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
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Applications Claiming Priority (2)
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| US64205805P | 2005-01-07 | 2005-01-07 | |
| PCT/IB2005/003937 WO2006072828A2 (en) | 2005-01-07 | 2005-12-22 | Heteroaromatic quinoline compounds and their use as pde10 inhibitors |
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| HRP20100461T1 true HRP20100461T1 (hr) | 2010-11-30 |
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| HR20100461T HRP20100461T1 (hr) | 2005-01-07 | 2010-08-19 | Heteroaromatični spojevi hinolina i njihova uporaba kao pde10 inhibitora |
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