RU2019144010A - Пиразолопиримидиновые ингибиторы pde9 - Google Patents
Пиразолопиримидиновые ингибиторы pde9 Download PDFInfo
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- 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
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- 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
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- 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
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- 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
-
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- 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
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- 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
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- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
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| 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 |
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| RU2019144010A true RU2019144010A (ru) | 2021-07-13 |
| RU2019144010A3 RU2019144010A3 (enExample) | 2021-10-01 |
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| KR20200013758A (ko) | 2017-06-08 | 2020-02-07 | 머크 샤프 앤드 돔 코포레이션 | 피라졸로피리미딘 pde9 억제제 |
| WO2020123272A1 (en) * | 2018-12-12 | 2020-06-18 | Merck Sharp & Dohme Corp. | Pyrazolopyrimidine pde9 inhibitors |
| US12247031B2 (en) | 2018-12-12 | 2025-03-11 | Merck Sharp & Dohme Llc | Cyclobutyl pyrazolopyrimidine PDE9 inhibitors |
| CA3132895C (en) * | 2019-03-08 | 2024-05-14 | 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 |
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| IE960442L (en) | 1988-12-27 | 1990-06-27 | Takeda Chemical Industries Ltd | Guanidine derivatives, their production and insecticides |
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| 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 |
| AU2001289751A1 (en) | 2000-08-01 | 2002-02-13 | Bayer Aktiengesellschaft | Selective pde 2 inhibitors, used as medicaments for improving cognition |
| US6770645B2 (en) | 2001-03-16 | 2004-08-03 | Pfizer Inc. | Pharmaceutically active compounds |
| US20030195205A1 (en) | 2001-11-02 | 2003-10-16 | Pfizer Inc. | PDE9 inhibitors for treating cardiovascular disorders |
| JP2005508978A (ja) | 2001-11-02 | 2005-04-07 | ファイザー・プロダクツ・インク | Ｐｄｅ９阻害薬によるインスリン抵抗性症候群及び２型糖尿病の治療 |
| 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 |
| JP5140418B2 (ja) | 2005-06-14 | 2013-02-06 | あすか製薬株式会社 | チエノピリミジン誘導体 |
| US8349850B2 (en) | 2006-03-28 | 2013-01-08 | Atir Holding S.A. | Heterocyclic compounds and uses thereof in the treatment of sexual disorders |
| ES2581573T3 (es) | 2006-08-08 | 2016-09-06 | Aska Pharmaceutical Co., Ltd. | Derivado de quinazolina |
| KR101555384B1 (ko) | 2006-12-13 | 2015-09-23 | 아스카 세이야쿠 가부시키가이샤 | 퀴녹살린 유도체 |
| DK2152712T3 (da) | 2007-05-11 | 2012-03-26 | Pfizer | Aminoheterocykliske fobindelser |
| PE20091211A1 (es) | 2007-11-30 | 2009-09-14 | Boehringer Ingelheim Int | Derivados de pirazolopirimidina como moduladores de pde9a |
| 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 |
| CA2736304A1 (en) | 2008-09-08 | 2010-03-11 | Boehringer Ingelheim International Gmbh | Pyrazolopyrimidines and their use for the treatment of cns disorders |
| TWI404721B (zh) | 2009-01-26 | 2013-08-11 | Pfizer | 胺基－雜環化合物 |
| GEP20146098B (en) | 2009-03-31 | 2014-05-27 | Boehringer Ingelheim Int | 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their usage as pde9a modulators |
| TW201118099A (en) | 2009-08-12 | 2011-06-01 | Boehringer Ingelheim Int | New compounds for the treatment of CNS disorders |
| MX344770B (es) * | 2010-08-12 | 2017-01-06 | Boehringer Ingelheim Int Gmbh * | Derivados de 6-cicloalquil-1,5-dihidro-pirazolo (3,4-d) pirimidin-4-onas y su uso como inhibidores de pde9a. |
| EP2669270B1 (en) | 2011-01-28 | 2018-01-03 | Sato Pharmaceutical Co., Ltd. | Indole-related compounds as urat1 inhibitors |
| 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 |
| CN104703987B (zh) | 2011-10-10 | 2017-05-03 | H.隆德贝克有限公司 | 具有咪唑并吡嗪酮骨架的pde9抑制剂 |
| 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 |
| EP3313852B1 (en) | 2015-06-25 | 2021-01-20 | 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 |
| US10370337B2 (en) | 2015-07-29 | 2019-08-06 | Merck, Sharp & Dohme Corp. | Oxy-cyanoquinolinone PDE9 inhibitors |
| WO2017019724A1 (en) | 2015-07-29 | 2017-02-02 | Merck Sharp & Dohme Corp. | Phenyl-cyanoquinolinone pde9 inhibitors |
| WO2017019723A1 (en) | 2015-07-29 | 2017-02-02 | Merck Sharp & Dohme Corp. | Aza-cyanoquinolinone pde9 inhibitors |
| KR20200013758A (ko) * | 2017-06-08 | 2020-02-07 | 머크 샤프 앤드 돔 코포레이션 | 피라졸로피리미딘 pde9 억제제 |
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- 2018-06-06 RU RU2019144010A patent/RU2019144010A/ru unknown
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- 2018-06-06 CN CN201880037972.4A patent/CN111051308A/zh active Pending
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| KR20200013758A (ko) | 2020-02-07 |
| CN111051308A (zh) | 2020-04-21 |
| US11028092B2 (en) | 2021-06-08 |
| EP3634964A1 (en) | 2020-04-15 |
| CA3064938A1 (en) | 2018-12-13 |
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| TW201902898A (zh) | 2019-01-16 |
| US10934294B2 (en) | 2021-03-02 |
| BR112019025813A2 (pt) | 2020-07-07 |
| AU2018281131A1 (en) | 2019-12-05 |
| AU2018281131B2 (en) | 2022-01-20 |
| JP2020523309A (ja) | 2020-08-06 |
| US20200140445A1 (en) | 2020-05-07 |
| WO2018226771A1 (en) | 2018-12-13 |
| MX2019014597A (es) | 2020-02-05 |
| MA53841A (fr) | 2021-09-22 |
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