RU2019144010A - Пиразолопиримидиновые ингибиторы pde9 - Google Patents
Пиразолопиримидиновые ингибиторы pde9 Download PDFInfo
- Publication number
- RU2019144010A RU2019144010A RU2019144010A RU2019144010A RU2019144010A RU 2019144010 A RU2019144010 A RU 2019144010A RU 2019144010 A RU2019144010 A RU 2019144010A RU 2019144010 A RU2019144010 A RU 2019144010A RU 2019144010 A RU2019144010 A RU 2019144010A
- Authority
- RU
- Russia
- Prior art keywords
- pyrazolo
- carbonitrile
- pyrimidine
- dihydro
- oxo
- Prior art date
Links
- 229940076380 PDE9 inhibitor Drugs 0.000 title 1
- 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 1
- -1 4 – oxo – 6 - ((1R, 2R) –2– (pyrimidin – 2 – yl) cyclobutyl) –1 - ((S) –1– (5– (trifluoromethyl) pyrazin – 2 – yl) ethyl) –4 , 5 – dihydro – 1H – pyrazolo [3,4 – d] pyrimidine Chemical compound 0.000 claims 57
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 57
- 150000003839 salts Chemical class 0.000 claims 14
- 150000001875 compounds Chemical class 0.000 claims 13
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 239000001257 hydrogen Substances 0.000 claims 10
- 150000002431 hydrogen Chemical class 0.000 claims 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000001424 substituent group Chemical group 0.000 claims 7
- 125000000217 alkyl group Chemical group 0.000 claims 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims 5
- 229910052731 fluorine Inorganic materials 0.000 claims 5
- 239000011737 fluorine Substances 0.000 claims 5
- 125000001153 fluoro group Chemical group F* 0.000 claims 5
- 238000000034 method Methods 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- IVUZZGZAKBPNAE-UHFFFAOYSA-N 2h-pyrazolo[3,4-d]pyrimidine-3-carbonitrile Chemical compound C1=NC=C2C(C#N)=NNC2=N1 IVUZZGZAKBPNAE-UHFFFAOYSA-N 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims 2
- 208000024254 Delusional disease Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 206010020772 Hypertension Diseases 0.000 claims 2
- 208000019022 Mood disease Diseases 0.000 claims 2
- 208000016285 Movement disease Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims 2
- 208000020832 chronic kidney disease Diseases 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 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 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 201000002545 drug psychosis Diseases 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 208000002851 paranoid schizophrenia Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 2
- 125000000335 thiazolyl group Chemical group 0.000 claims 2
- BFKYQYMHJANOTR-UHFFFAOYSA-N 2h-pyrimidine-1-carbonitrile Chemical compound N#CN1CN=CC=C1 BFKYQYMHJANOTR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- DCEDXXOLOACMFX-KBRIMQKVSA-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-KBRIMQKVSA-N 0.000 claims 1
- 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 1
- 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 1
- BXEKIWVRPOTJNA-JEYLPNPQSA-N C(C)(C)(C)C1=NC(=NC=C1)C1C(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)C1C(CC1)C=1NC(C2=C(N=1)N(N=C2C#N)[C@@H](C)C=1C=NC(=CC=1)C(F)(F)F)=O BXEKIWVRPOTJNA-JEYLPNPQSA-N 0.000 claims 1
- VMABGNBOHHGZNG-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 VMABGNBOHHGZNG-UHFFFAOYSA-N 0.000 claims 1
- DFKCKCZESWJKRM-UHFFFAOYSA-N C1(CC1)C1=CC=C(C=N1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=C(C=N1)F)C#N Chemical compound C1(CC1)C1=CC=C(C=N1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=C(C=N1)F)C#N DFKCKCZESWJKRM-UHFFFAOYSA-N 0.000 claims 1
- GFVBNEXQGQGAKO-UHFFFAOYSA-N C1(CC1)C1=CC=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=CC=C(C=N1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N GFVBNEXQGQGAKO-UHFFFAOYSA-N 0.000 claims 1
- GFVBNEXQGQGAKO-XYPHTWIQSA-N C1(CC1)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 Chemical compound C1(CC1)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 GFVBNEXQGQGAKO-XYPHTWIQSA-N 0.000 claims 1
- DFKCKCZESWJKRM-DQYPLSBCSA-N C1(CC1)C1=CC=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=CC=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 DFKCKCZESWJKRM-DQYPLSBCSA-N 0.000 claims 1
- GFVBNEXQGQGAKO-COXVUDFISA-N C1(CC1)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 Chemical compound C1(CC1)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 GFVBNEXQGQGAKO-COXVUDFISA-N 0.000 claims 1
- GFVBNEXQGQGAKO-KBRIMQKVSA-N C1(CC1)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 Chemical compound C1(CC1)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 GFVBNEXQGQGAKO-KBRIMQKVSA-N 0.000 claims 1
- GFVBNEXQGQGAKO-XOKHGSTOSA-N C1(CC1)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 Chemical compound C1(CC1)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 GFVBNEXQGQGAKO-XOKHGSTOSA-N 0.000 claims 1
- GFVBNEXQGQGAKO-XKQJLSEDSA-N C1(CC1)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 Chemical compound C1(CC1)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 GFVBNEXQGQGAKO-XKQJLSEDSA-N 0.000 claims 1
- DFKCKCZESWJKRM-ZLIFDBKOSA-N C1(CC1)C1=CC=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=CC=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 DFKCKCZESWJKRM-ZLIFDBKOSA-N 0.000 claims 1
- GFVBNEXQGQGAKO-JQFCIGGWSA-N C1(CC1)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 Chemical compound C1(CC1)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 GFVBNEXQGQGAKO-JQFCIGGWSA-N 0.000 claims 1
- DFKCKCZESWJKRM-JCURWCKSSA-N C1(CC1)C1=CC=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=CC=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 DFKCKCZESWJKRM-JCURWCKSSA-N 0.000 claims 1
- GFVBNEXQGQGAKO-IAOVAPTHSA-N C1(CC1)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 Chemical compound C1(CC1)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 GFVBNEXQGQGAKO-IAOVAPTHSA-N 0.000 claims 1
- GPFRQZOJIQJLJV-UHFFFAOYSA-N C1(CC1)C1=NC=C(C=N1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=C(C=N1)F)C#N Chemical compound C1(CC1)C1=NC=C(C=N1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=C(C=N1)F)C#N GPFRQZOJIQJLJV-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- GPFRQZOJIQJLJV-RLCCDNCMSA-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-RLCCDNCMSA-N 0.000 claims 1
- FEPNMKDMRNRDPJ-KCXAZCMYSA-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-KCXAZCMYSA-N 0.000 claims 1
- GPFRQZOJIQJLJV-HFBAOOFYSA-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-HFBAOOFYSA-N 0.000 claims 1
- FEPNMKDMRNRDPJ-DAXOMENPSA-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-DAXOMENPSA-N 0.000 claims 1
- 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 1
- 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 1
- GPFRQZOJIQJLJV-IUIKQTSFSA-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-IUIKQTSFSA-N 0.000 claims 1
- 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 1
- IZUNLAVGPGXIDZ-UHFFFAOYSA-N C1(CC1)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 C1(CC1)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 IZUNLAVGPGXIDZ-UHFFFAOYSA-N 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 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 1
- LNHVCZNICIGKBT-NWANDNLSSA-N CC1=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 CC1=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 LNHVCZNICIGKBT-NWANDNLSSA-N 0.000 claims 1
- LNHVCZNICIGKBT-BPLDGKMQSA-N CC1=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 CC1=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 LNHVCZNICIGKBT-BPLDGKMQSA-N 0.000 claims 1
- DBCMPEFUKVOJOC-UHFFFAOYSA-N CC=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 CC=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 DBCMPEFUKVOJOC-UHFFFAOYSA-N 0.000 claims 1
- DBCMPEFUKVOJOC-SNPRPXQTSA-N CC=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 CC=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 DBCMPEFUKVOJOC-SNPRPXQTSA-N 0.000 claims 1
- 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 1
- SFIWAZKKXJUERW-XBFCOCLRSA-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-XBFCOCLRSA-N 0.000 claims 1
- SFIWAZKKXJUERW-MRVWCRGKSA-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-MRVWCRGKSA-N 0.000 claims 1
- 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 1
- SFIWAZKKXJUERW-IACUBPJLSA-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-IACUBPJLSA-N 0.000 claims 1
- NGEUQIJGBKRGTR-UHFFFAOYSA-N COC=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 COC=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 NGEUQIJGBKRGTR-UHFFFAOYSA-N 0.000 claims 1
- 206010007558 Cardiac failure chronic Diseases 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- MKKQXYGRZYERLN-UHFFFAOYSA-N ClC=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 ClC=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 MKKQXYGRZYERLN-UHFFFAOYSA-N 0.000 claims 1
- 101100407341 Drosophila melanogaster Pde9 gene Proteins 0.000 claims 1
- XSPADNFKOXOWIQ-UHFFFAOYSA-N FC(C1=CC=C(C=N1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N)F Chemical compound FC(C1=CC=C(C=N1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N)F XSPADNFKOXOWIQ-UHFFFAOYSA-N 0.000 claims 1
- XSPADNFKOXOWIQ-BNOWGMLFSA-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-BNOWGMLFSA-N 0.000 claims 1
- XSPADNFKOXOWIQ-XBFCOCLRSA-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-XBFCOCLRSA-N 0.000 claims 1
- XSPADNFKOXOWIQ-MRVWCRGKSA-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-MRVWCRGKSA-N 0.000 claims 1
- XSPADNFKOXOWIQ-KWCYVHTRSA-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-KWCYVHTRSA-N 0.000 claims 1
- 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 1
- XSPADNFKOXOWIQ-UBHSHLNASA-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-UBHSHLNASA-N 0.000 claims 1
- XSPADNFKOXOWIQ-IACUBPJLSA-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-IACUBPJLSA-N 0.000 claims 1
- XSPADNFKOXOWIQ-FPMFFAJLSA-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-FPMFFAJLSA-N 0.000 claims 1
- 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 1
- HHQGAUAHYUEZOF-UHFFFAOYSA-N FC(OC=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(OC=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 HHQGAUAHYUEZOF-UHFFFAOYSA-N 0.000 claims 1
- HAWIPJVSLZKKOE-UHFFFAOYSA-N FC1=CC=C(C=C1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N Chemical compound FC1=CC=C(C=C1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N HAWIPJVSLZKKOE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 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 1
- 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 1
- 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 1
- LYRPKBQNNKHMEZ-UHFFFAOYSA-N FC=1C=C(C=CC=1F)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N Chemical compound FC=1C=C(C=CC=1F)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N LYRPKBQNNKHMEZ-UHFFFAOYSA-N 0.000 claims 1
- LYRPKBQNNKHMEZ-XBFCOCLRSA-N FC=1C=C(C=CC=1F)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N Chemical compound FC=1C=C(C=CC=1F)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N LYRPKBQNNKHMEZ-XBFCOCLRSA-N 0.000 claims 1
- LYRPKBQNNKHMEZ-MRVWCRGKSA-N FC=1C=C(C=CC=1F)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N Chemical compound FC=1C=C(C=CC=1F)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N LYRPKBQNNKHMEZ-MRVWCRGKSA-N 0.000 claims 1
- LYRPKBQNNKHMEZ-UBHSHLNASA-N FC=1C=C(C=CC=1F)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N Chemical compound FC=1C=C(C=CC=1F)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N LYRPKBQNNKHMEZ-UBHSHLNASA-N 0.000 claims 1
- LYRPKBQNNKHMEZ-IACUBPJLSA-N FC=1C=C(C=CC=1F)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N Chemical compound FC=1C=C(C=CC=1F)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N LYRPKBQNNKHMEZ-IACUBPJLSA-N 0.000 claims 1
- SLCWMIUYDJFWJQ-UHFFFAOYSA-N FC=1C=C(C=NC=1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N Chemical compound FC=1C=C(C=NC=1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N SLCWMIUYDJFWJQ-UHFFFAOYSA-N 0.000 claims 1
- SLCWMIUYDJFWJQ-UGFHNGPFSA-N FC=1C=C(C=NC=1)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N Chemical compound FC=1C=C(C=NC=1)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N SLCWMIUYDJFWJQ-UGFHNGPFSA-N 0.000 claims 1
- SLCWMIUYDJFWJQ-KCPJHIHWSA-N FC=1C=C(C=NC=1)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N Chemical compound FC=1C=C(C=NC=1)[C@@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N SLCWMIUYDJFWJQ-KCPJHIHWSA-N 0.000 claims 1
- SLCWMIUYDJFWJQ-CQDKDKBSSA-N FC=1C=C(C=NC=1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N Chemical compound FC=1C=C(C=NC=1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N SLCWMIUYDJFWJQ-CQDKDKBSSA-N 0.000 claims 1
- SLCWMIUYDJFWJQ-NILFDRSVSA-N FC=1C=C(C=NC=1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N Chemical compound FC=1C=C(C=NC=1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N SLCWMIUYDJFWJQ-NILFDRSVSA-N 0.000 claims 1
- NHDGCCYJHZJHQV-UHFFFAOYSA-N FC=1C=CC(=NC=1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N Chemical compound FC=1C=CC(=NC=1)C(C)N1N=C(C2=C1N=C(NC2=O)C1C(CC1)C1=NC=CC=N1)C#N NHDGCCYJHZJHQV-UHFFFAOYSA-N 0.000 claims 1
- NHDGCCYJHZJHQV-YUTCNCBUSA-N FC=1C=CC(=NC=1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@@H](CC1)C1=NC=CC=N1)C#N Chemical compound FC=1C=CC(=NC=1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@@H](CC1)C1=NC=CC=N1)C#N NHDGCCYJHZJHQV-YUTCNCBUSA-N 0.000 claims 1
- NHDGCCYJHZJHQV-UBHSHLNASA-N FC=1C=CC(=NC=1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N Chemical compound FC=1C=CC(=NC=1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@@H]1[C@H](CC1)C1=NC=CC=N1)C#N NHDGCCYJHZJHQV-UBHSHLNASA-N 0.000 claims 1
- NHDGCCYJHZJHQV-IACUBPJLSA-N FC=1C=CC(=NC=1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N Chemical compound FC=1C=CC(=NC=1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@@H](CC1)C1=NC=CC=N1)C#N NHDGCCYJHZJHQV-IACUBPJLSA-N 0.000 claims 1
- NHDGCCYJHZJHQV-FPMFFAJLSA-N FC=1C=CC(=NC=1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@H](CC1)C1=NC=CC=N1)C#N Chemical compound FC=1C=CC(=NC=1)[C@H](C)N1N=C(C2=C1N=C(NC2=O)[C@H]1[C@H](CC1)C1=NC=CC=N1)C#N NHDGCCYJHZJHQV-FPMFFAJLSA-N 0.000 claims 1
- 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 1
- SUDCPSKTLHFPRM-UHFFFAOYSA-N FC=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 FC=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 SUDCPSKTLHFPRM-UHFFFAOYSA-N 0.000 claims 1
- WWBTYSYBUPIFQD-CQDKDKBSSA-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)C1CCOCC1)=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)C1CCOCC1)=O WWBTYSYBUPIFQD-CQDKDKBSSA-N 0.000 claims 1
- WWBTYSYBUPIFQD-UGFHNGPFSA-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)C1CCOCC1)=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)C1CCOCC1)=O WWBTYSYBUPIFQD-UGFHNGPFSA-N 0.000 claims 1
- WWBTYSYBUPIFQD-NILFDRSVSA-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)C1CCOCC1)=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)C1CCOCC1)=O WWBTYSYBUPIFQD-NILFDRSVSA-N 0.000 claims 1
- WWBTYSYBUPIFQD-KCPJHIHWSA-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)C1CCOCC1)=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)C1CCOCC1)=O WWBTYSYBUPIFQD-KCPJHIHWSA-N 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 claims 1
- HUJVIDLHYSWEKF-UHFFFAOYSA-N O=C1C2=C(N=C(N1)C1C(CC1)C1=NC=CC=N1)N(N=C2C#N)C(C)C1=CC(=CC=C1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)C1C(CC1)C1=NC=CC=N1)N(N=C2C#N)C(C)C1=CC(=CC=C1)C(F)(F)F HUJVIDLHYSWEKF-UHFFFAOYSA-N 0.000 claims 1
- BKGRGWITJPSOOJ-UHFFFAOYSA-N O=C1C2=C(N=C(N1)C1C(CC1)C1=NC=CC=N1)N(N=C2C#N)C(C)C1=CC=C(C=C1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)C1C(CC1)C1=NC=CC=N1)N(N=C2C#N)C(C)C1=CC=C(C=C1)C(F)(F)F BKGRGWITJPSOOJ-UHFFFAOYSA-N 0.000 claims 1
- ZLKHKMHQLQQIOC-UHFFFAOYSA-N O=C1C2=C(N=C(N1)C1C(CC1)C1=NC=CC=N1)N(N=C2C#N)C(C)C1=CN=C(S1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)C1C(CC1)C1=NC=CC=N1)N(N=C2C#N)C(C)C1=CN=C(S1)C(F)(F)F ZLKHKMHQLQQIOC-UHFFFAOYSA-N 0.000 claims 1
- SESUHSGADRECQZ-UHFFFAOYSA-N O=C1C2=C(N=C(N1)C1C(CC1)C1=NC=CC=N1)N(N=C2C#N)C(C)C1=NC=C(N=C1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)C1C(CC1)C1=NC=CC=N1)N(N=C2C#N)C(C)C1=NC=C(N=C1)C(F)(F)F SESUHSGADRECQZ-UHFFFAOYSA-N 0.000 claims 1
- BLVLZOOVHIZKPF-UHFFFAOYSA-N O=C1C2=C(N=C(N1)C1C(CC1)C1=NC=CC=N1)N(N=C2C#N)C(C)C1CCOCC1 Chemical compound O=C1C2=C(N=C(N1)C1C(CC1)C1=NC=CC=N1)N(N=C2C#N)C(C)C1CCOCC1 BLVLZOOVHIZKPF-UHFFFAOYSA-N 0.000 claims 1
- AGJXXEHLPVMHRJ-UHFFFAOYSA-N O=C1C2=C(N=C(N1)C1C(CC1)C1=NC=CC=N1)N(N=C2C#N)C(C)C=1C=NC(=CC=1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)C1C(CC1)C1=NC=CC=N1)N(N=C2C#N)C(C)C=1C=NC(=CC=1)C(F)(F)F AGJXXEHLPVMHRJ-UHFFFAOYSA-N 0.000 claims 1
- GKGGELBUPDPMFR-UHFFFAOYSA-N O=C1C2=C(N=C(N1)C1C(CC1)C1=NC=CC=N1)N(N=C2C#N)C(C)C=1C=NC(=NC=1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)C1C(CC1)C1=NC=CC=N1)N(N=C2C#N)C(C)C=1C=NC(=NC=1)C(F)(F)F GKGGELBUPDPMFR-UHFFFAOYSA-N 0.000 claims 1
- MAOBYZNMOOJWQP-UHFFFAOYSA-N O=C1C2=C(N=C(N1)C1C(CC1)C1=NC=CC=N1)N(N=C2C#N)CC=1C=NC(=CC=1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)C1C(CC1)C1=NC=CC=N1)N(N=C2C#N)CC=1C=NC(=CC=1)C(F)(F)F MAOBYZNMOOJWQP-UHFFFAOYSA-N 0.000 claims 1
- MAOBYZNMOOJWQP-STQMWFEESA-N O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)CC=1C=NC(=CC=1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)CC=1C=NC(=CC=1)C(F)(F)F MAOBYZNMOOJWQP-STQMWFEESA-N 0.000 claims 1
- HUJVIDLHYSWEKF-RCBQFDQVSA-N O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C1=CC(=CC=C1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C1=CC(=CC=C1)C(F)(F)F HUJVIDLHYSWEKF-RCBQFDQVSA-N 0.000 claims 1
- BKGRGWITJPSOOJ-RCBQFDQVSA-N O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C1=CC=C(C=C1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C1=CC=C(C=C1)C(F)(F)F BKGRGWITJPSOOJ-RCBQFDQVSA-N 0.000 claims 1
- ZLKHKMHQLQQIOC-DCAQKATOSA-N O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C1=CN=C(S1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C1=CN=C(S1)C(F)(F)F ZLKHKMHQLQQIOC-DCAQKATOSA-N 0.000 claims 1
- SESUHSGADRECQZ-SRVKXCTJSA-N O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C1=NC=C(N=C1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C1=NC=C(N=C1)C(F)(F)F SESUHSGADRECQZ-SRVKXCTJSA-N 0.000 claims 1
- BLVLZOOVHIZKPF-QEJZJMRPSA-N O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C1CCOCC1 Chemical compound O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C1CCOCC1 BLVLZOOVHIZKPF-QEJZJMRPSA-N 0.000 claims 1
- AGJXXEHLPVMHRJ-UBHSHLNASA-N O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C=1C=NC(=CC=1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C=1C=NC(=CC=1)C(F)(F)F AGJXXEHLPVMHRJ-UBHSHLNASA-N 0.000 claims 1
- GKGGELBUPDPMFR-DRZSPHRISA-N O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C=1C=NC(=NC=1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C=1C=NC(=NC=1)C(F)(F)F GKGGELBUPDPMFR-DRZSPHRISA-N 0.000 claims 1
- HUJVIDLHYSWEKF-KCXAZCMYSA-N O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1=CC(=CC=C1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1=CC(=CC=C1)C(F)(F)F HUJVIDLHYSWEKF-KCXAZCMYSA-N 0.000 claims 1
- BKGRGWITJPSOOJ-KCXAZCMYSA-N O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1=CC=C(C=C1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1=CC=C(C=C1)C(F)(F)F BKGRGWITJPSOOJ-KCXAZCMYSA-N 0.000 claims 1
- ZLKHKMHQLQQIOC-VWYCJHECSA-N O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1=CN=C(S1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1=CN=C(S1)C(F)(F)F ZLKHKMHQLQQIOC-VWYCJHECSA-N 0.000 claims 1
- SESUHSGADRECQZ-WOPDTQHZSA-N O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1=NC=C(N=C1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1=NC=C(N=C1)C(F)(F)F SESUHSGADRECQZ-WOPDTQHZSA-N 0.000 claims 1
- BLVLZOOVHIZKPF-SNPRPXQTSA-N O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1CCOCC1 Chemical compound O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1CCOCC1 BLVLZOOVHIZKPF-SNPRPXQTSA-N 0.000 claims 1
- AGJXXEHLPVMHRJ-XBFCOCLRSA-N O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C=1C=NC(=CC=1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C=1C=NC(=CC=1)C(F)(F)F AGJXXEHLPVMHRJ-XBFCOCLRSA-N 0.000 claims 1
- GKGGELBUPDPMFR-WXHSDQCUSA-N O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C=1C=NC(=NC=1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@@H]1[C@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C=1C=NC(=NC=1)C(F)(F)F GKGGELBUPDPMFR-WXHSDQCUSA-N 0.000 claims 1
- MAOBYZNMOOJWQP-CHWSQXEVSA-N O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)CC=1C=NC(=CC=1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)CC=1C=NC(=CC=1)C(F)(F)F MAOBYZNMOOJWQP-CHWSQXEVSA-N 0.000 claims 1
- HUJVIDLHYSWEKF-APHBMKBZSA-N O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C1=CC(=CC=C1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C1=CC(=CC=C1)C(F)(F)F HUJVIDLHYSWEKF-APHBMKBZSA-N 0.000 claims 1
- BKGRGWITJPSOOJ-APHBMKBZSA-N O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C1=CC=C(C=C1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C1=CC=C(C=C1)C(F)(F)F BKGRGWITJPSOOJ-APHBMKBZSA-N 0.000 claims 1
- ZLKHKMHQLQQIOC-HBNTYKKESA-N O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C1=CN=C(S1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C1=CN=C(S1)C(F)(F)F ZLKHKMHQLQQIOC-HBNTYKKESA-N 0.000 claims 1
- BLVLZOOVHIZKPF-NWANDNLSSA-N O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C1CCOCC1 Chemical compound O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C1CCOCC1 BLVLZOOVHIZKPF-NWANDNLSSA-N 0.000 claims 1
- AGJXXEHLPVMHRJ-IACUBPJLSA-N O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C=1C=NC(=CC=1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C=1C=NC(=CC=1)C(F)(F)F AGJXXEHLPVMHRJ-IACUBPJLSA-N 0.000 claims 1
- GKGGELBUPDPMFR-CYZMBNFOSA-N O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C=1C=NC(=NC=1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@@H](C)C=1C=NC(=NC=1)C(F)(F)F GKGGELBUPDPMFR-CYZMBNFOSA-N 0.000 claims 1
- HUJVIDLHYSWEKF-DAXOMENPSA-N O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1=CC(=CC=C1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1=CC(=CC=C1)C(F)(F)F HUJVIDLHYSWEKF-DAXOMENPSA-N 0.000 claims 1
- BKGRGWITJPSOOJ-DAXOMENPSA-N O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1=CC=C(C=C1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1=CC=C(C=C1)C(F)(F)F BKGRGWITJPSOOJ-DAXOMENPSA-N 0.000 claims 1
- ZLKHKMHQLQQIOC-GMTAPVOTSA-N O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1=CN=C(S1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1=CN=C(S1)C(F)(F)F ZLKHKMHQLQQIOC-GMTAPVOTSA-N 0.000 claims 1
- SESUHSGADRECQZ-IJLUTSLNSA-N O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1=NC=C(N=C1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1=NC=C(N=C1)C(F)(F)F SESUHSGADRECQZ-IJLUTSLNSA-N 0.000 claims 1
- BLVLZOOVHIZKPF-BPLDGKMQSA-N O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1CCOCC1 Chemical compound O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C1CCOCC1 BLVLZOOVHIZKPF-BPLDGKMQSA-N 0.000 claims 1
- AGJXXEHLPVMHRJ-MRVWCRGKSA-N O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C=1C=NC(=CC=1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C=1C=NC(=CC=1)C(F)(F)F AGJXXEHLPVMHRJ-MRVWCRGKSA-N 0.000 claims 1
- GKGGELBUPDPMFR-RAIGVLPGSA-N O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C=1C=NC(=NC=1)C(F)(F)F Chemical compound O=C1C2=C(N=C(N1)[C@H]1[C@@H](CC1)C1=NC=CC=N1)N(N=C2C#N)[C@H](C)C=1C=NC(=NC=1)C(F)(F)F GKGGELBUPDPMFR-RAIGVLPGSA-N 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Classifications
-
- 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
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762516903P | 2017-06-08 | 2017-06-08 | |
| US62/516,903 | 2017-06-08 | ||
| US201862665840P | 2018-05-02 | 2018-05-02 | |
| US62/665,840 | 2018-05-02 | ||
| PCT/US2018/036172 WO2018226771A1 (en) | 2017-06-08 | 2018-06-06 | Pyrazolopyrimidine pde9 inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2019144010A true RU2019144010A (ru) | 2021-07-13 |
| RU2019144010A3 RU2019144010A3 (https=) | 2021-10-01 |
Family
ID=62779024
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2019144010A RU2019144010A (ru) | 2017-06-08 | 2018-06-06 | Пиразолопиримидиновые ингибиторы pde9 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US10934294B2 (https=) |
| EP (1) | EP3634964B1 (https=) |
| JP (1) | JP2020523309A (https=) |
| KR (1) | KR20200013758A (https=) |
| CN (1) | CN111051308A (https=) |
| AU (1) | AU2018281131B2 (https=) |
| BR (1) | BR112019025813A2 (https=) |
| CA (1) | CA3064938A1 (https=) |
| MA (1) | MA53841A (https=) |
| MX (1) | MX2019014597A (https=) |
| RU (1) | RU2019144010A (https=) |
| TW (1) | TW201902898A (https=) |
| WO (1) | WO2018226771A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2019144010A (ru) * | 2017-06-08 | 2021-07-13 | Мерк Шарп И Доум Корп. | Пиразолопиримидиновые ингибиторы pde9 |
| EP3893881B1 (en) * | 2018-12-12 | 2024-10-09 | Merck Sharp & Dohme LLC | Cyclobutyl pyrazolopyrimidine pde9 inhibitors |
| WO2020123272A1 (en) * | 2018-12-12 | 2020-06-18 | Merck Sharp & Dohme Corp. | Pyrazolopyrimidine pde9 inhibitors |
| SG11202109781QA (en) | 2019-03-08 | 2021-10-28 | Transthera Sciences Nanjing Inc | Uses of phosphodiesterase inhibitors |
| WO2021253180A1 (en) * | 2020-06-15 | 2021-12-23 | Novartis Ag | Methyl (r) -2- (fluoromethyl) -5-oxo-4-phenyl-4, 5, 6, 7-tetrahydro-1h-cyclopenta [b] pyridine-3-carboxylate and methyl (r) -2- (fluoromethyl) -5-oxo-4-phenyl-1, 4, 5, 7-tetrahydrofuro [3, 4-b] pyridine-3-carboxylate as cav1.2 activators |
| CN114773256B (zh) * | 2022-03-23 | 2024-05-03 | 中国农业大学 | 一种4-氰基哌啶的合成方法 |
| CN117582909B (zh) * | 2024-01-19 | 2024-04-02 | 天津凯莱英医药科技发展有限公司 | 一种连续生产5-单硝酸异山梨酯的系统和方法 |
| CN120329388B (zh) * | 2025-04-30 | 2025-09-26 | 中日友好医院(中日友好临床医学研究所) | 一种双靶点多肽及其在心衰治疗中的应用 |
Family Cites Families (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE960441L (en) | 1988-12-27 | 1990-06-27 | Takeda Chemical Industries Ltd | Guanidine derivatives, their production and insecticides |
| US5294612A (en) | 1992-03-30 | 1994-03-15 | Sterling Winthrop Inc. | 6-heterocyclyl pyrazolo [3,4-d]pyrimidin-4-ones and compositions and method of use thereof |
| DE19709877A1 (de) | 1997-03-11 | 1998-09-17 | Bayer Ag | 1,5-Dihydro-pyrazolo[3,4-d]-pyrimidinon-derivate |
| CZ27399A3 (cs) | 1999-01-26 | 2000-08-16 | Ústav Experimentální Botaniky Av Čr | Substituované dusíkaté heterocyklické deriváty, způsob jejich přípravy, tyto deriváty pro použití jako léčiva, farmaceutická kompozice a kombinovaný farmaceutický přípravek tyto deriváty obsahující a použití těchto derivátů pro výrobu léčiv |
| WO2002009713A2 (de) | 2000-08-01 | 2002-02-07 | Bayer Aktiengesellschaft | Selektive pde 2-inhibitoren als arzneimittel zur verbesserung der wahrnehmung |
| US6770645B2 (en) | 2001-03-16 | 2004-08-03 | Pfizer Inc. | Pharmaceutically active compounds |
| EP1444009A1 (en) | 2001-11-02 | 2004-08-11 | Pfizer Products Inc. | Treatment of insulin resistance syndrome and type 2 diabetes with pde9 inhibitors |
| US20030195205A1 (en) | 2001-11-02 | 2003-10-16 | Pfizer Inc. | PDE9 inhibitors for treating cardiovascular disorders |
| DE10238722A1 (de) | 2002-08-23 | 2004-03-11 | Bayer Ag | Selektive Phosphodiesterase 9A-Inhibitoren als Arzneimittel zur Verbesserung kognitiver Prozesse |
| DE10328479A1 (de) | 2003-06-25 | 2005-01-13 | Bayer Ag | 6-Arylamino-5-cyano-4-pyrimidinone |
| WO2006135080A1 (ja) | 2005-06-14 | 2006-12-21 | Aska Pharmaceutical Co., Ltd. | チエノピリミジン誘導体 |
| EP2010505B1 (en) | 2006-03-28 | 2012-12-05 | Atir Holding S.A. | Heterocyclic compounds and uses thereof in the treatment of sexual disorders |
| AU2007282678B2 (en) | 2006-08-08 | 2012-09-27 | Aska Pharmaceutical Co., Ltd. | Quinazoline derivative |
| CA2671980C (en) | 2006-12-13 | 2015-05-05 | Aska Pharmaceutical Co., Ltd. | Quinoxaline derivatives |
| PT2152712E (pt) | 2007-05-11 | 2012-02-29 | Pfizer | Compostos amino-heterocíclicos |
| JP5498392B2 (ja) | 2007-11-30 | 2014-05-21 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | １，５−ジヒドロ−ピラゾロ［３，４−ｄ］ピリミジン−４−オン誘導体及びｃｎｓ障害の治療のためのｐｄｅ９ａモジュレーターとしてのそれらの使用 |
| US9089572B2 (en) | 2008-01-17 | 2015-07-28 | California Institute Of Technology | Inhibitors of p97 |
| UA105362C2 (en) | 2008-04-02 | 2014-05-12 | Бьорингер Ингельхайм Интернациональ Гмбх | 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators |
| JP5453431B2 (ja) | 2008-09-08 | 2014-03-26 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ピラゾロピリミジン及びｃｎｓ障害の治療のためのそれらの使用 |
| TWI404721B (zh) | 2009-01-26 | 2013-08-11 | Pfizer | 胺基－雜環化合物 |
| PE20120505A1 (es) | 2009-03-31 | 2012-05-09 | Boehringer Ingelheim Int | Derivados de 1-heterociclil-1,5-dihidro-pirazolo[3,4-d]pirimidin-4-ona como moduladores de pde9a |
| AR077859A1 (es) | 2009-08-12 | 2011-09-28 | Boehringer Ingelheim Int | Compuestos para el tratamiento de trastornos del snc |
| AP2012006631A0 (en) * | 2010-08-12 | 2012-12-31 | Boehringer Ingelheim Int | 6-Cycloalkyl-1, 5-dihydro-pyrazolo[3,4-D] pyrimidin-4-one derivatives and their use as PDE9A inhibitors |
| WO2012102405A1 (ja) | 2011-01-28 | 2012-08-02 | 佐藤製薬株式会社 | 縮環化合物 |
| US20130040971A1 (en) * | 2011-02-14 | 2013-02-14 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of cns disorders |
| US8809345B2 (en) | 2011-02-15 | 2014-08-19 | Boehringer Ingelheim International Gmbh | 6-cycloalkyl-pyrazolopyrimidinones for the treatment of CNS disorders |
| SG11201502728WA (en) | 2011-10-10 | 2015-05-28 | Lundbeck & Co As H | Pde9i with imidazo pyrazinone backbone |
| TW201348231A (zh) | 2012-02-29 | 2013-12-01 | Amgen Inc | 雜雙環化合物 |
| KR101706216B1 (ko) | 2012-04-03 | 2017-02-13 | 한화테크윈 주식회사 | 고밀도 삼차원 영상 재구성 장치 및 방법 |
| WO2014024125A1 (en) | 2012-08-08 | 2014-02-13 | Celon Pharma S.A. | Pyrazolo[4,3-d]pyrimidin-7(6h)-one derivatives as pde9 inhibitors |
| US10174032B2 (en) | 2014-05-05 | 2019-01-08 | Signalrx Pharmaceuticals, Inc. | Heterocyclic compound classes for signaling modulation |
| WO2016191935A1 (en) | 2015-05-29 | 2016-12-08 | Merck Sharp & Dohme Corp. | 6-alkyl dihydropyrazolopyrimidinone compounds as pde2 inhibitors |
| US10647727B2 (en) | 2015-06-25 | 2020-05-12 | Merck Sharp & Dohme Corp. | Substituted pyrazolo/imidazolo bicyclic compounds as PDE2 inhibitors |
| WO2017000276A1 (en) | 2015-07-01 | 2017-01-05 | Merck Sharp & Dohme Corp. | Bicyclic heterocyclic compounds as pde2 inhibitors |
| US10370336B2 (en) | 2015-07-29 | 2019-08-06 | Merck Sharp & Dohme Corp. | Phenyl-cyanoquinolinone PDE9 inhibitors |
| WO2017019723A1 (en) | 2015-07-29 | 2017-02-02 | Merck Sharp & Dohme Corp. | Aza-cyanoquinolinone pde9 inhibitors |
| WO2017019726A1 (en) | 2015-07-29 | 2017-02-02 | Merck Sharp & Dohme Corp. | Oxy-cyanoquinolinone pde9 inhibitors |
| RU2019144010A (ru) * | 2017-06-08 | 2021-07-13 | Мерк Шарп И Доум Корп. | Пиразолопиримидиновые ингибиторы pde9 |
-
2018
- 2018-06-06 RU RU2019144010A patent/RU2019144010A/ru unknown
- 2018-06-06 MX MX2019014597A patent/MX2019014597A/es unknown
- 2018-06-06 US US16/001,295 patent/US10934294B2/en active Active
- 2018-06-06 BR BR112019025813-2A patent/BR112019025813A2/pt not_active Application Discontinuation
- 2018-06-06 MA MA053841A patent/MA53841A/fr unknown
- 2018-06-06 WO PCT/US2018/036172 patent/WO2018226771A1/en not_active Ceased
- 2018-06-06 CA CA3064938A patent/CA3064938A1/en active Pending
- 2018-06-06 KR KR1020207000123A patent/KR20200013758A/ko not_active Withdrawn
- 2018-06-06 JP JP2019567341A patent/JP2020523309A/ja active Pending
- 2018-06-06 TW TW107119410A patent/TW201902898A/zh unknown
- 2018-06-06 CN CN201880037972.4A patent/CN111051308A/zh active Pending
- 2018-06-06 AU AU2018281131A patent/AU2018281131B2/en not_active Ceased
- 2018-06-06 EP EP18735038.4A patent/EP3634964B1/en active Active
-
2019
- 2019-10-31 US US16/670,093 patent/US11028092B2/en active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US11028092B2 (en) | 2021-06-08 |
| US10934294B2 (en) | 2021-03-02 |
| BR112019025813A2 (pt) | 2020-07-07 |
| AU2018281131B2 (en) | 2022-01-20 |
| US20180354955A1 (en) | 2018-12-13 |
| RU2019144010A3 (https=) | 2021-10-01 |
| EP3634964B1 (en) | 2022-02-23 |
| US20200140445A1 (en) | 2020-05-07 |
| CN111051308A (zh) | 2020-04-21 |
| WO2018226771A1 (en) | 2018-12-13 |
| MA53841A (fr) | 2021-09-22 |
| TW201902898A (zh) | 2019-01-16 |
| CA3064938A1 (en) | 2018-12-13 |
| EP3634964A1 (en) | 2020-04-15 |
| JP2020523309A (ja) | 2020-08-06 |
| AU2018281131A1 (en) | 2019-12-05 |
| KR20200013758A (ko) | 2020-02-07 |
| MX2019014597A (es) | 2020-02-05 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU2019144010A (ru) | Пиразолопиримидиновые ингибиторы pde9 | |
| JP7088983B2 (ja) | キナーゼ阻害剤としてのビアリールアミド化合物 | |
| KR102702236B1 (ko) | Ror 감마 조절제로서의 치환된 테트라하이드로퀴놀리논 화합물 | |
| JP7576581B2 (ja) | イミダゾ［１，２－ａ］ピリジニル誘導体及び疾患の処置におけるそれらの使用 | |
| US9718804B2 (en) | GSK-3 inhibitors | |
| WO2020150626A1 (en) | Imidazo[1,2-a]pyridinyl derivatives as irak4 inhibitors | |
| AU2016219183B2 (en) | Substituted pyrazole compounds as RORgammaT inhibitors and uses thereof | |
| RS51768B (sr) | Derivati pirazolpiridina | |
| MX2013011612A (es) | Derivados de pirrolo[2,3-d]pirimidina como inhibidores de quinasa relacionados con tropomiosina. | |
| KR20130130030A (ko) | Vps34 억제제로서의 비-헤테로아릴 화합물 | |
| EP3191478A1 (en) | Compounds and compositions as raf kinase inhibitors | |
| US8828990B2 (en) | N-7 substituted purine and pyrazolopyrimine compounds, compositions and methods of use | |
| RU2020114670A (ru) | Бициклические соединения для применения в качестве ингибиторов rip1 киназы | |
| JP2020523309A5 (https=) | ||
| EP3548484A1 (en) | Bicyclic amide compounds and methods of use thereof | |
| JP2018508554A5 (https=) | ||
| JP2025521780A (ja) | リウマチ性関節炎の処置のためのＳＩＫモジュレーターとしてのイミダゾ［４，５－ｃ］ピリジン誘導体 | |
| EP4522612A1 (en) | Tyk2 inhibitors | |
| CN114630822B (zh) | 联芳基二氢乳清酸脱氢酶抑制剂 | |
| JPWO2020168143A5 (https=) | ||
| WO2023250064A1 (en) | Tyrosine kinase 2 inhibitors and uses thereof | |
| CN116323582B (zh) | 杂芳环类化合物及其用途 | |
| CA3226950A1 (en) | Fused ring heteroaryl compounds and use thereof | |
| WO2026046976A1 (en) | Pyrazolopyridine phosphate esters for modulating salt-inducible kinase (sik) | |
| HK40095637B (zh) | 杂芳环类化合物及其用途 |