BR112019025813A2 - inibidores de pirazolopirimidina pde9 - Google Patents

Info

Publication number

BR112019025813A2

BR112019025813A2 BR112019025813-2A BR112019025813A BR112019025813A2 BR 112019025813 A2 BR112019025813 A2 BR 112019025813A2 BR 112019025813 A BR112019025813 A BR 112019025813A BR 112019025813 A2 BR112019025813 A2 BR 112019025813A2

Authority

BR

Brazil

Prior art keywords

ethyl

dihydro

oxo

pyrimidine

carbonitrile

Prior art date

2017-06-08

Links

• Espacenet
• Global Dossier
• Discuss

• OGEBRHQLRGFBNV-RZDIXWSQSA-N chembl2036808 Chemical compound C12=NC(NCCCC)=NC=C2C(C=2C=CC(F)=CC=2)=NN1C[C@H]1CC[C@H](N)CC1 OGEBRHQLRGFBNV-RZDIXWSQSA-N 0.000 title abstract description 3
• 239000003112 inhibitor Substances 0.000 title description 15
• 150000001875 compounds Chemical class 0.000 claims abstract description 235
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 69
• 208000035475 disorder Diseases 0.000 claims abstract description 46
• 208000028017 Psychotic disease Diseases 0.000 claims abstract description 20
• 238000011282 treatment Methods 0.000 claims abstract description 18
• 206010020772 Hypertension Diseases 0.000 claims abstract description 14
• 208000026106 cerebrovascular disease Diseases 0.000 claims abstract description 12
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 11
• 230000004064 dysfunction Effects 0.000 claims abstract description 8
• 208000020832 chronic kidney disease Diseases 0.000 claims abstract description 6
• 206010007558 Cardiac failure chronic Diseases 0.000 claims abstract description 3
• -1 4-oxo-6- (2- (pyrimidin-2-yl) cyclobutyl) -1- (1- (5- (trifluoromethyl) pyrazin-2-yl) ethyl) - 4,5-dihydro-1H-pyrazole Chemical compound 0.000 claims description 186
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 99
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 56
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 56
• 238000000034 method Methods 0.000 claims description 54
• 150000003839 salts Chemical class 0.000 claims description 53
• BFKYQYMHJANOTR-UHFFFAOYSA-N 2h-pyrimidine-1-carbonitrile Chemical compound N#CN1CN=CC=C1 BFKYQYMHJANOTR-UHFFFAOYSA-N 0.000 claims description 50
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 37
• 239000011737 fluorine Substances 0.000 claims description 35
• 229910052731 fluorine Inorganic materials 0.000 claims description 35
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 239000001257 hydrogen Substances 0.000 claims description 34
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 30
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
• 125000001424 substituent group Chemical group 0.000 claims description 24
• 201000010099 disease Diseases 0.000 claims description 23
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 16
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• FEPNMKDMRNRDPJ-UHFFFAOYSA-N C1(CC1)C1=NC=C(C=N1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N Chemical compound C1(CC1)C1=NC=C(C=N1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N FEPNMKDMRNRDPJ-UHFFFAOYSA-N 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 208000019901 Anxiety disease Diseases 0.000 claims description 11
• 206010019280 Heart failures Diseases 0.000 claims description 11
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 11
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 11
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 11
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
• 125000000335 thiazolyl group Chemical group 0.000 claims description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
• 229910052736 halogen Inorganic materials 0.000 claims description 8
• 150000002367 halogens Chemical class 0.000 claims description 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
• 208000019022 Mood disease Diseases 0.000 claims description 7
• 239000000460 chlorine Substances 0.000 claims description 6
• 229910052801 chlorine Inorganic materials 0.000 claims description 6
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
• JERSLDYYZIQFKX-BPUTZDHNSA-N CC1=NC(=NC(=C1)C)[C@@H]1[C@H](CC1)C=1NC(C2=C(N=1)N(N=C2C#N)[C@@H](C)C=1C=NC(=CC=1)C(F)(F)F)=O Chemical compound CC1=NC(=NC(=C1)C)[C@@H]1[C@H](CC1)C=1NC(C2=C(N=1)N(N=C2C#N)[C@@H](C)C=1C=NC(=CC=1)C(F)(F)F)=O JERSLDYYZIQFKX-BPUTZDHNSA-N 0.000 claims description 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• WWBTYSYBUPIFQD-UHFFFAOYSA-N FC=1C=NC(=NC=1)C1C(CC1)C=1NC(C2=C(N=1)N(N=C2C#N)C(C)C1CCOCC1)=O Chemical compound FC=1C=NC(=NC=1)C1C(CC1)C=1NC(C2=C(N=1)N(N=C2C#N)C(C)C1CCOCC1)=O WWBTYSYBUPIFQD-UHFFFAOYSA-N 0.000 claims description 4
• 150000002431 hydrogen Chemical group 0.000 claims description 4
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
• 238000002560 therapeutic procedure Methods 0.000 claims description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
• QLSVPIXLPXOJOW-UHFFFAOYSA-N CC1(C(CC1)C1=NC=CC=N1)C=1NC(C2=C(N=1)N(N=C2C#N)C(C)C=1C=NC(=CC=1)C(F)(F)F)=O Chemical compound CC1(C(CC1)C1=NC=CC=N1)C=1NC(C2=C(N=1)N(N=C2C#N)C(C)C=1C=NC(=CC=1)C(F)(F)F)=O QLSVPIXLPXOJOW-UHFFFAOYSA-N 0.000 claims description 3
• 208000024254 Delusional disease Diseases 0.000 claims description 3
• 208000016285 Movement disease Diseases 0.000 claims description 3
• 208000011963 Substance-induced psychotic disease Diseases 0.000 claims description 3
• 231100000393 Substance-induced psychotic disorder Toxicity 0.000 claims description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
• 229910052794 bromium Inorganic materials 0.000 claims description 3
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
• 208000002851 paranoid schizophrenia Diseases 0.000 claims description 3
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
• XFDDEQWMKKNJEL-APHBMKBZSA-N C(#C)C=1C=NC(=NC=1)[C@H]1[C@@H](CC1)C=1NC(C2=C(N=1)N(N=C2C#N)[C@@H](C)C=1C=NC(=CC=1)C(F)(F)F)=O Chemical compound C(#C)C=1C=NC(=NC=1)[C@H]1[C@@H](CC1)C=1NC(C2=C(N=1)N(N=C2C#N)[C@@H](C)C=1C=NC(=CC=1)C(F)(F)F)=O XFDDEQWMKKNJEL-APHBMKBZSA-N 0.000 claims description 2
• DCEDXXOLOACMFX-UHFFFAOYSA-N C(#N)C1=CC=C(C=C1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N Chemical compound C(#N)C1=CC=C(C=C1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N DCEDXXOLOACMFX-UHFFFAOYSA-N 0.000 claims description 2
• DCEDXXOLOACMFX-JQFCIGGWSA-N C(#N)C1=CC=C(C=C1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N Chemical compound C(#N)C1=CC=C(C=C1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N DCEDXXOLOACMFX-JQFCIGGWSA-N 0.000 claims description 2
• DCEDXXOLOACMFX-IAOVAPTHSA-N C(#N)C1=CC=C(C=C1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N Chemical compound C(#N)C1=CC=C(C=C1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N DCEDXXOLOACMFX-IAOVAPTHSA-N 0.000 claims description 2
• ZZJGDDUSWIREGY-SZMVWBNQSA-N C(C)(C)(C)C1=NC(=NC(=C1)C(C)(C)C)[C@@H]1[C@H](CC1)C=1NC(C2=C(N=1)N(N=C2C#N)[C@@H](C)C=1C=NC(=CC=1)C(F)(F)F)=O Chemical compound C(C)(C)(C)C1=NC(=NC(=C1)C(C)(C)C)[C@@H]1[C@H](CC1)C=1NC(C2=C(N=1)N(N=C2C#N)[C@@H](C)C=1C=NC(=CC=1)C(F)(F)F)=O ZZJGDDUSWIREGY-SZMVWBNQSA-N 0.000 claims description 2
• ZZJGDDUSWIREGY-CGTJXYLNSA-N C(C)(C)(C)C1=NC(=NC(=C1)C(C)(C)C)[C@H]1[C@@H](CC1)C=1NC(C2=C(N=1)N(N=C2C#N)[C@@H](C)C=1C=NC(=CC=1)C(F)(F)F)=O Chemical compound C(C)(C)(C)C1=NC(=NC(=C1)C(C)(C)C)[C@H]1[C@@H](CC1)C=1NC(C2=C(N=1)N(N=C2C#N)[C@@H](C)C=1C=NC(=CC=1)C(F)(F)F)=O ZZJGDDUSWIREGY-CGTJXYLNSA-N 0.000 claims description 2
• ZZJGDDUSWIREGY-KBAYOESNSA-N C(C)(C)(C)C1=NC(=NC(=C1)C(C)(C)C)[C@H]1[C@@H](CC1)C=1NC(C2=C(N=1)N(N=C2C#N)[C@H](C)C=1C=NC(=CC=1)C(F)(F)F)=O Chemical compound C(C)(C)(C)C1=NC(=NC(=C1)C(C)(C)C)[C@H]1[C@@H](CC1)C=1NC(C2=C(N=1)N(N=C2C#N)[C@H](C)C=1C=NC(=CC=1)C(F)(F)F)=O ZZJGDDUSWIREGY-KBAYOESNSA-N 0.000 claims description 2
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• MOWSUDBENVUAHH-APHBMKBZSA-N C1(CC1)C1=NC(=NC=C1)[C@H]1[C@@H](CC1)C=1NC(C2=C(N=1)N(N=C2C#N)[C@@H](C)C=1C=NC(=CC=1)C(F)(F)F)=O Chemical compound C1(CC1)C1=NC(=NC=C1)[C@H]1[C@@H](CC1)C=1NC(C2=C(N=1)N(N=C2C#N)[C@@H](C)C=1C=NC(=CC=1)C(F)(F)F)=O MOWSUDBENVUAHH-APHBMKBZSA-N 0.000 claims description 2
• GPFRQZOJIQJLJV-UVBJJODRSA-N C1(CC1)C1=NC=C(C=N1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=C(C=N1)F)C#N Chemical compound C1(CC1)C1=NC=C(C=N1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=C(C=N1)F)C#N GPFRQZOJIQJLJV-UVBJJODRSA-N 0.000 claims description 2
• FEPNMKDMRNRDPJ-RCBQFDQVSA-N C1(CC1)C1=NC=C(C=N1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N Chemical compound C1(CC1)C1=NC=C(C=N1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N FEPNMKDMRNRDPJ-RCBQFDQVSA-N 0.000 claims description 2
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• FEPNMKDMRNRDPJ-APHBMKBZSA-N C1(CC1)C1=NC=C(C=N1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N Chemical compound C1(CC1)C1=NC=C(C=N1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N FEPNMKDMRNRDPJ-APHBMKBZSA-N 0.000 claims description 2
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
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• SFIWAZKKXJUERW-UHFFFAOYSA-N CN1N=CC(=C1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N Chemical compound CN1N=CC(=C1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N SFIWAZKKXJUERW-UHFFFAOYSA-N 0.000 claims description 2
• SFIWAZKKXJUERW-UBHSHLNASA-N CN1N=CC(=C1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N Chemical compound CN1N=CC(=C1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N SFIWAZKKXJUERW-UBHSHLNASA-N 0.000 claims description 2
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• XSPADNFKOXOWIQ-YUTCNCBUSA-N FC(C1=CC=C(C=N1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@@H](CC1)C1=NC=CC=N1)C#N)F Chemical compound FC(C1=CC=C(C=N1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@@H](CC1)C1=NC=CC=N1)C#N)F XSPADNFKOXOWIQ-YUTCNCBUSA-N 0.000 claims description 2
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• PNFZXYGCZQPOCD-UHFFFAOYSA-N FC(C=1C=NC(=NC=1)C1C(CC1)C=1NC(C2=C(N=1)N(N=C2C#N)C(C)C=1C=NC(=CC=1)C(F)(F)F)=O)F Chemical compound FC(C=1C=NC(=NC=1)C1C(CC1)C=1NC(C2=C(N=1)N(N=C2C#N)C(C)C=1C=NC(=CC=1)C(F)(F)F)=O)F PNFZXYGCZQPOCD-UHFFFAOYSA-N 0.000 claims description 2
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