CA2944801C - Analogs of 4h-pyrazolo[1,5-a]benzimidazole compounds as parp inhibitors - Google Patents

Analogs of 4h-pyrazolo[1,5-a]benzimidazole compounds as parp inhibitors Download PDF

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Publication number
CA2944801C
CA2944801C CA2944801A CA2944801A CA2944801C CA 2944801 C CA2944801 C CA 2944801C CA 2944801 A CA2944801 A CA 2944801A CA 2944801 A CA2944801 A CA 2944801A CA 2944801 C CA2944801 C CA 2944801C
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Prior art keywords
fluoro
benzo
imidazo
carboxamide
pyrazole
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CA2944801A
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English (en)
French (fr)
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CA2944801A1 (en
Inventor
Zhaozhong DING
Shuhui Chen
Gang Li
Cailin WANG
Zhibo Zhang
Xuehai WANG
Yong Xu
Lie LI
Ronghua TU
Yang Yue
Hailiang Chen
Wenjie Sun
Lu Huang
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hubei Bio-Pharmaceutical Industrial Technological Institute Inc
HUMANWELL HEALTHCARE (GROUP) Co Ltd
Original Assignee
Hubei Bio-Pharmaceutical Industrial Technological Institute Inc
HUMANWELL HEALTHCARE (GROUP) Co Ltd
Medshine Discovery Inc
Priority date (The priority date 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 date listed.)
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Priority claimed from CN201410144173.0A external-priority patent/CN104974161B/zh
Application filed by Hubei Bio-Pharmaceutical Industrial Technological Institute Inc, HUMANWELL HEALTHCARE (GROUP) Co Ltd, Medshine Discovery Inc filed Critical Hubei Bio-Pharmaceutical Industrial Technological Institute Inc
Publication of CA2944801A1 publication Critical patent/CA2944801A1/en
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    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A61K31/4162—1,2-Diazoles condensed with heterocyclic ring 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/4164—1,3-Diazoles
    • A61K31/4184—1,3-Diazoles condensed with carbocyclic rings, e.g. benzimidazoles
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/42—Oxazoles
    • A61K31/424—Oxazoles condensed with heterocyclic ring systems, e.g. clavulanic acid
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/429—Thiazoles condensed with heterocyclic ring systems
    • 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
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • 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
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
    • C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
    • C07D513/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Epidemiology (AREA)
  • Diabetes (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Vascular Medicine (AREA)
  • Emergency Medicine (AREA)
  • Endocrinology (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Urology & Nephrology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
CA2944801A 2014-04-10 2015-03-30 Analogs of 4h-pyrazolo[1,5-a]benzimidazole compounds as parp inhibitors Active CA2944801C (en)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
CN201410144173.0A CN104974161B (zh) 2014-04-10 2014-04-10 作为PARP抑制剂的4H-吡唑并[1,5-α]苯并咪唑化合物的类似物
CN201410144173.0 2014-04-10
CN201510113090.X 2015-03-13
CN201510113090 2015-03-13
PCT/CN2015/075363 WO2015154630A1 (zh) 2014-04-10 2015-03-30 作为PARP抑制剂的4H-吡唑并[1,5-α]苯并咪唑化合物的类似物

Publications (2)

Publication Number Publication Date
CA2944801A1 CA2944801A1 (en) 2015-10-15
CA2944801C true CA2944801C (en) 2019-02-12

Family

ID=54287319

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2944801A Active CA2944801C (en) 2014-04-10 2015-03-30 Analogs of 4h-pyrazolo[1,5-a]benzimidazole compounds as parp inhibitors

Country Status (22)

Country Link
US (1) US9856262B2 (en:Method)
EP (1) EP3130592B1 (en:Method)
JP (1) JP6359175B2 (en:Method)
KR (1) KR101921486B1 (en:Method)
CN (1) CN106459057B (en:Method)
AU (1) AU2015245786B2 (en:Method)
BR (1) BR112016023397B1 (en:Method)
CA (1) CA2944801C (en:Method)
DK (1) DK3130592T3 (en:Method)
ES (1) ES2754590T3 (en:Method)
HU (1) HUE047410T2 (en:Method)
IL (1) IL248258B (en:Method)
MX (1) MX368496B (en:Method)
NZ (1) NZ725165A (en:Method)
PL (1) PL3130592T3 (en:Method)
PT (1) PT3130592T (en:Method)
RU (1) RU2672722C2 (en:Method)
SA (1) SA516380051B1 (en:Method)
SG (1) SG11201608438YA (en:Method)
TW (1) TWI671301B (en:Method)
WO (1) WO2015154630A1 (en:Method)
ZA (1) ZA201607736B (en:Method)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104974161B (zh) * 2014-04-10 2019-11-01 湖北生物医药产业技术研究院有限公司 作为PARP抑制剂的4H-吡唑并[1,5-α]苯并咪唑化合物的类似物
AU2016333293B2 (en) * 2015-09-30 2020-07-30 Hubei Bio-Pharmaceutical Industrial Technological Institute Inc. Salt type and crystal type of 4H-pyrazolo (1, 5-alpha) benzimidazole compound and preparation method and intermediate thereof
WO2017156350A1 (en) 2016-03-09 2017-09-14 K-Gen, Inc. Methods of cancer treatment
ES2998110T3 (en) 2017-04-27 2025-02-19 Elanco Animal Health Gmbh New bicyclic pyrazole derivatives
CN115028641B (zh) * 2022-07-19 2024-05-28 湖南大学 一种钴催化合成5,8-双官能团取代咪唑并[1,2-a]吡嗪类化合物的方法
TW202508595A (zh) 2023-05-04 2025-03-01 美商銳新醫藥公司 用於ｒａｓ相關疾病或病症之組合療法
WO2025034702A1 (en) 2023-08-07 2025-02-13 Revolution Medicines, Inc. Rmc-6291 for use in the treatment of ras protein-related disease or disorder
WO2025056690A1 (en) 2023-09-12 2025-03-20 MAX-PLANCK-Gesellschaft zur Förderung der Wissenschaften e.V. Parp1- and immune-checkpoint inhibitors for the treatment of cancer patients overexpressing ubqln1 and/or ubqln4
CN116969954B (zh) * 2023-09-21 2023-11-28 广东省农业科学院农业质量标准与监测技术研究所 一类含内酰胺的三环稠合杂环化合物及其应用
US20250154171A1 (en) 2023-10-12 2025-05-15 Revolution Medicines, Inc. Ras inhibitors
CN117534677B (zh) * 2024-01-09 2024-03-12 广东省农业科学院农业质量标准与监测技术研究所 一类含亚胺的三环稠合杂环化合物及其应用
WO2025171296A1 (en) 2024-02-09 2025-08-14 Revolution Medicines, Inc. Ras inhibitors
WO2025217307A1 (en) 2024-04-09 2025-10-16 Revolution Medicines, Inc. Methods for predicting response to a ras(on) inhibitor and combination therapies
WO2025240847A1 (en) 2024-05-17 2025-11-20 Revolution Medicines, Inc. Ras inhibitors

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4916051A (en) * 1987-04-07 1990-04-10 Konica Corporation Silver halide color photographic light-sensitive material
NZ547990A (en) * 2003-12-22 2010-04-30 Smithkline Beecham Cork Ltd CRF receptor antagonists and methods relating thereto
WO2007076127A2 (en) 2005-12-22 2007-07-05 Biogen Idec Ma Inc Condensed imidazoles or pyrazoles and their use as transforming growth factor modulators
WO2007144669A1 (en) * 2006-06-15 2007-12-21 Istituto Di Ricerche Di Biologia Molecolare P. Angeletti Spa Pyrazolo[1,5-a]quinazolin-5(4h)-ones as inhibitors of poly(adp-ribose)polymerase (parp)
EP2069351B1 (en) * 2006-06-20 2015-10-28 AbbVie Inc. Pyrazoloquinazolinones as parp inhibitors
GB0701273D0 (en) * 2007-01-24 2007-02-28 Angeletti P Ist Richerche Bio New compounds
DK2656843T3 (en) 2012-04-26 2015-04-20 Helmut Schickaneder Esters of bendamustine and related compounds, and medical use thereof
KR20150006873A (ko) * 2012-05-04 2015-01-19 메르크 파텐트 게엠베하 피롤로트리아지논 유도체
EP2666775A1 (en) * 2012-05-21 2013-11-27 Domain Therapeutics Substituted pyrazoloquinazolinones and pyrroloquinazolinones as allosteric modulators of group II metabotropic glutamate receptors
MX2014014832A (es) 2012-06-07 2015-02-12 Hoffmann La Roche Pirrolopirimidona y pirrolopiridona, inhibidores de tanquirasa.
IN2015MN00002A (en:Method) 2012-07-09 2015-10-16 Lupin Ltd
CN103570725B (zh) 2012-08-01 2017-03-22 中国科学院上海药物研究所 哌嗪并三唑类化合物及其制备方法和用途
ES2773272T3 (es) * 2012-08-08 2020-07-10 Merck Patent Gmbh Derivados de (aza-)isoquinolinona
CN104974161B (zh) 2014-04-10 2019-11-01 湖北生物医药产业技术研究院有限公司 作为PARP抑制剂的4H-吡唑并[1,5-α]苯并咪唑化合物的类似物

Also Published As

Publication number Publication date
DK3130592T3 (da) 2019-11-04
KR101921486B1 (ko) 2018-11-26
CA2944801A1 (en) 2015-10-15
TW201620913A (zh) 2016-06-16
TWI671301B (zh) 2019-09-11
WO2015154630A1 (zh) 2015-10-15
RU2016144202A (ru) 2018-05-15
CN106459057B (zh) 2019-06-07
NZ725165A (en) 2018-04-27
ZA201607736B (en) 2017-09-27
CN106459057A (zh) 2017-02-22
HUE047410T2 (hu) 2020-04-28
MX368496B (es) 2019-10-04
SA516380051B1 (ar) 2020-05-17
US9856262B2 (en) 2018-01-02
RU2016144202A3 (en:Method) 2018-05-15
EP3130592B1 (en) 2019-08-14
BR112016023397B1 (pt) 2022-08-16
EP3130592A4 (en) 2017-09-06
JP2017510653A (ja) 2017-04-13
US20170029430A1 (en) 2017-02-02
SG11201608438YA (en) 2016-11-29
MX2016013265A (es) 2017-05-03
AU2015245786A1 (en) 2016-11-03
JP6359175B2 (ja) 2018-07-18
PL3130592T3 (pl) 2020-05-18
BR112016023397A2 (en:Method) 2017-08-15
AU2015245786B2 (en) 2018-03-15
PT3130592T (pt) 2019-11-21
RU2672722C2 (ru) 2018-11-19
IL248258B (en) 2018-11-29
KR20170005807A (ko) 2017-01-16
ES2754590T3 (es) 2020-04-20
EP3130592A1 (en) 2017-02-15

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