KR20200013758A - 피라졸로피리미딘 pde9 억제제 - Google Patents

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Publication number

KR20200013758A

KR20200013758A KR1020207000123A KR20207000123A KR20200013758A KR 20200013758 A KR20200013758 A KR 20200013758A KR 1020207000123 A KR1020207000123 A KR 1020207000123A KR 20207000123 A KR20207000123 A KR 20207000123A KR 20200013758 A KR20200013758 A KR 20200013758A

Authority

KR

South Korea

Prior art keywords

ethyl

pyrimidine

pyrazolo

oxo

carbonitrile

Prior art date

2017-06-08

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Withdrawn

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• 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
• 229940076380 PDE9 inhibitor Drugs 0.000 title description 8
• RVEJWGYZBXCGGM-DNVCBOLYSA-N chembl2179094 Chemical compound C([C@H]([C@@H](C1)C=2NC(=O)C=3C=NN(C=3N=2)C2CCOCC2)C)N1CC1=CC=CC=C1 RVEJWGYZBXCGGM-DNVCBOLYSA-N 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims abstract description 239
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 73
• 208000035475 disorder Diseases 0.000 claims abstract description 51
• 238000011282 treatment Methods 0.000 claims abstract description 30
• 208000028017 Psychotic disease Diseases 0.000 claims abstract description 23
• 206010020772 Hypertension Diseases 0.000 claims abstract description 16
• 208000026106 cerebrovascular disease Diseases 0.000 claims abstract description 13
• 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 12
• 230000004064 dysfunction Effects 0.000 claims abstract description 12
• 208000020832 chronic kidney disease Diseases 0.000 claims abstract description 7
• 206010007558 Cardiac failure chronic Diseases 0.000 claims abstract description 5
• -1 2- (pyrimidin-2-yl) cyclobutyl Chemical group 0.000 claims description 112
• 150000003839 salts Chemical class 0.000 claims description 54
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 53
• 238000000034 method Methods 0.000 claims description 49
• 229910052739 hydrogen Inorganic materials 0.000 claims description 36
• 239000001257 hydrogen Substances 0.000 claims description 36
• 125000001153 fluoro group Chemical group F* 0.000 claims description 34
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
• 125000001424 substituent group Chemical group 0.000 claims description 24
• 125000000217 alkyl group Chemical group 0.000 claims description 22
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 20
• 201000010099 disease Diseases 0.000 claims description 20
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 17
• 208000019901 Anxiety disease Diseases 0.000 claims description 15
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 14
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
• 239000008194 pharmaceutical composition Substances 0.000 claims description 12
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
• 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
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 125000000335 thiazolyl group Chemical group 0.000 claims description 11
• 208000019022 Mood disease Diseases 0.000 claims description 10
• 150000002431 hydrogen Chemical class 0.000 claims description 10
• 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 8
• 229910052736 halogen Inorganic materials 0.000 claims description 8
• 150000002367 halogens Chemical class 0.000 claims description 8
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 8
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
• 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
• 208000024254 Delusional disease Diseases 0.000 claims description 5
• 208000011963 Substance-induced psychotic disease Diseases 0.000 claims description 5
• 231100000393 Substance-induced psychotic disorder Toxicity 0.000 claims description 5
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
• 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 5
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
• 208000015122 neurodegenerative disease Diseases 0.000 claims description 5
• 208000002851 paranoid schizophrenia Diseases 0.000 claims description 5
• 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 5
• XFDDEQWMKKNJEL-UHFFFAOYSA-N C(#C)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 Chemical compound C(#C)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 XFDDEQWMKKNJEL-UHFFFAOYSA-N 0.000 claims description 4
• 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
• SUDCPSKTLHFPRM-BPNCWPANSA-N FC=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 FC=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 SUDCPSKTLHFPRM-BPNCWPANSA-N 0.000 claims description 4
• SUDCPSKTLHFPRM-ZLKJLUDKSA-N FC=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 FC=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 SUDCPSKTLHFPRM-ZLKJLUDKSA-N 0.000 claims description 4
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 238000002560 therapeutic procedure Methods 0.000 claims description 4
• HAWIPJVSLZKKOE-KCXAZCMYSA-N FC1=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 FC1=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 HAWIPJVSLZKKOE-KCXAZCMYSA-N 0.000 claims description 3
• HAWIPJVSLZKKOE-DAXOMENPSA-N FC1=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 FC1=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 HAWIPJVSLZKKOE-DAXOMENPSA-N 0.000 claims description 3
• HAWIPJVSLZKKOE-RCBQFDQVSA-N FC1=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 FC1=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 HAWIPJVSLZKKOE-RCBQFDQVSA-N 0.000 claims description 3
• HAWIPJVSLZKKOE-APHBMKBZSA-N FC1=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 FC1=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 HAWIPJVSLZKKOE-APHBMKBZSA-N 0.000 claims description 3
• 125000001246 bromo group Chemical group Br* 0.000 claims description 3
• HPFLLZGQKSUDNM-UHFFFAOYSA-N BrC=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 Chemical compound BrC=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 HPFLLZGQKSUDNM-UHFFFAOYSA-N 0.000 claims description 2
• HPFLLZGQKSUDNM-BPNCWPANSA-N BrC=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 BrC=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 HPFLLZGQKSUDNM-BPNCWPANSA-N 0.000 claims description 2
• HPFLLZGQKSUDNM-SWHYSGLUSA-N BrC=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 BrC=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 HPFLLZGQKSUDNM-SWHYSGLUSA-N 0.000 claims description 2
• HPFLLZGQKSUDNM-ZLKJLUDKSA-N BrC=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 BrC=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 HPFLLZGQKSUDNM-ZLKJLUDKSA-N 0.000 claims description 2
• HPFLLZGQKSUDNM-LERXQTSPSA-N BrC=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 BrC=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 HPFLLZGQKSUDNM-LERXQTSPSA-N 0.000 claims description 2
• XFDDEQWMKKNJEL-RCBQFDQVSA-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-RCBQFDQVSA-N 0.000 claims description 2
• XFDDEQWMKKNJEL-KCXAZCMYSA-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-KCXAZCMYSA-N 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
• XFDDEQWMKKNJEL-DAXOMENPSA-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-DAXOMENPSA-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-COXVUDFISA-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-COXVUDFISA-N 0.000 claims description 2
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