CA3005495C - 1,3,4-thiadiazole compounds and their use in treating cancer - Google Patents

1,3,4-thiadiazole compounds and their use in treating cancer Download PDF

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Publication number
CA3005495C
CA3005495C CA3005495A CA3005495A CA3005495C CA 3005495 C CA3005495 C CA 3005495C CA 3005495 A CA3005495 A CA 3005495A CA 3005495 A CA3005495 A CA 3005495A CA 3005495 C CA3005495 C CA 3005495C
Authority
CA
Canada
Prior art keywords
methoxy
thiadiazol
mmol
pyridazin
ylpyrrolidin
Prior art date
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.)
Active
Application number
CA3005495A
Other languages
English (en)
French (fr)
Other versions
CA3005495A1 (en
Inventor
Maurice Raymond Verschoyle Finlay
Johannes Wilhelmus Maria Nissink
Mark David Charles
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.)
Cancer Research Technology Ltd
AstraZeneca AB
Original Assignee
Cancer Research Technology Ltd
AstraZeneca AB
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.)
Filing date
Publication date
Application filed by Cancer Research Technology Ltd, AstraZeneca AB filed Critical Cancer Research Technology Ltd
Publication of CA3005495A1 publication Critical patent/CA3005495A1/en
Application granted granted Critical
Publication of CA3005495C publication Critical patent/CA3005495C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
    • 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
    • A61K31/50—Pyridazines; Hydrogenated pyridazines
    • A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
    • 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
    • A61K31/53—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with three nitrogens as the only ring hetero atoms, e.g. chlorazanil, melamine
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Medicinal Preparation (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
CA3005495A 2015-11-30 2016-11-30 1,3,4-thiadiazole compounds and their use in treating cancer Active CA3005495C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562260789P 2015-11-30 2015-11-30
US62/260,789 2015-11-30
PCT/EP2016/079250 WO2017093299A1 (en) 2015-11-30 2016-11-30 1,3,4-thiadiazole compounds and their use in treating cancer

Publications (2)

Publication Number Publication Date
CA3005495A1 CA3005495A1 (en) 2017-06-08
CA3005495C true CA3005495C (en) 2023-12-12

Family

ID=57485461

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3005495A Active CA3005495C (en) 2015-11-30 2016-11-30 1,3,4-thiadiazole compounds and their use in treating cancer

Country Status (24)

Country Link
US (3) US10323028B2 (enExample)
EP (1) EP3383873B1 (enExample)
JP (1) JP6999550B2 (enExample)
KR (1) KR20180083942A (enExample)
CN (1) CN108349966B (enExample)
AR (1) AR106874A1 (enExample)
AU (1) AU2016363718B2 (enExample)
BR (1) BR112018010806A2 (enExample)
CA (1) CA3005495C (enExample)
CL (1) CL2018001407A1 (enExample)
CO (1) CO2018006928A2 (enExample)
EA (1) EA201891241A1 (enExample)
ES (1) ES2914333T3 (enExample)
IL (1) IL259510A (enExample)
MX (1) MX2018006532A (enExample)
NI (1) NI201800064A (enExample)
PE (1) PE20181565A1 (enExample)
PH (1) PH12018501131A1 (enExample)
RU (1) RU2018123714A (enExample)
SG (1) SG11201803810XA (enExample)
SV (1) SV2018005702A (enExample)
TN (1) TN2018000127A1 (enExample)
TW (1) TW201733587A (enExample)
WO (1) WO2017093299A1 (enExample)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB201520959D0 (en) 2015-11-27 2016-01-13 Astrazeneca Ab And Cancer Res Technology Ltd Bis-pyridazine compounds and their use in treating cancer
US9938265B2 (en) 2015-11-30 2018-04-10 Astrazeneca Ab 1,3,4-thiadiazole compounds and their use in treating cancer
TW201731511A (zh) * 2015-11-30 2017-09-16 阿斯特捷利康公司 1,3,4-噻二唑化合物及其在治療癌症中之用途
US10323028B2 (en) 2015-11-30 2019-06-18 Astrazeneca Ab 1,3,4-thiadiazole compounds and their use in treating cancer
CN110741003B (zh) * 2017-06-13 2021-07-23 南京明德新药研发有限公司 作为gls1抑制剂的化合物
ES2939506T3 (es) 2018-10-16 2023-04-24 Medshine Discovery Inc Derivado de tiadiazol y usos del mismo como inhibidor de GLS1 para el tratamiento de cáncer
WO2025196446A1 (en) * 2024-03-22 2025-09-25 Sitryx Therapeutics Limited Thiadiazoles as glutaminase 1 inhibitors

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6451828B1 (en) * 2000-08-10 2002-09-17 Elan Pharmaceuticals, Inc. Selective inhibition of glutaminase by bis-thiadiazoles
CN108785305B (zh) * 2011-11-21 2021-10-29 卡利泰拉生物科技公司 谷氨酰胺酶的杂环抑制剂
HUE056078T2 (hu) * 2012-11-16 2022-01-28 Calithera Biosciences Inc Heterociklusos glutamináz inhibitorok
WO2014079011A1 (en) 2012-11-22 2014-05-30 Agios Pharmaceuticals, Inc. Heterocyclic compounds for inhibiting glutaminase and their methods of use
KR20160100407A (ko) 2014-01-06 2016-08-23 리젠 파마슈티컬스 소시에떼 아노님 신규한 글루타미나제의 저해제
WO2015138902A1 (en) * 2014-03-14 2015-09-17 Calithera Biosciences, Inc. Combination therapy with glutaminase inhibitors
GB201409624D0 (en) 2014-05-30 2014-07-16 Astrazeneca Ab 1,3,4-thiadiazole compounds and their use in treating cancer
GB201520959D0 (en) 2015-11-27 2016-01-13 Astrazeneca Ab And Cancer Res Technology Ltd Bis-pyridazine compounds and their use in treating cancer
US9938265B2 (en) * 2015-11-30 2018-04-10 Astrazeneca Ab 1,3,4-thiadiazole compounds and their use in treating cancer
TW201731511A (zh) 2015-11-30 2017-09-16 阿斯特捷利康公司 1,3,4-噻二唑化合物及其在治療癌症中之用途
US10323028B2 (en) 2015-11-30 2019-06-18 Astrazeneca Ab 1,3,4-thiadiazole compounds and their use in treating cancer

Also Published As

Publication number Publication date
US11753405B2 (en) 2023-09-12
SG11201803810XA (en) 2018-06-28
CL2018001407A1 (es) 2018-10-12
MX2018006532A (es) 2019-05-15
US20170152255A1 (en) 2017-06-01
JP2018535986A (ja) 2018-12-06
PE20181565A1 (es) 2018-10-03
WO2017093299A1 (en) 2017-06-08
CN108349966A (zh) 2018-07-31
BR112018010806A2 (en) 2018-11-27
CA3005495A1 (en) 2017-06-08
EP3383873A1 (en) 2018-10-10
AU2016363718B2 (en) 2019-11-14
SV2018005702A (es) 2018-11-27
US10323028B2 (en) 2019-06-18
PH12018501131A1 (en) 2019-01-21
AU2016363718A1 (en) 2018-07-12
US20210246131A1 (en) 2021-08-12
CN108349966B (zh) 2022-02-15
NI201800064A (es) 2018-10-18
JP6999550B2 (ja) 2022-02-10
ES2914333T3 (es) 2022-06-09
TN2018000127A1 (en) 2019-10-04
TW201733587A (zh) 2017-10-01
RU2018123714A (ru) 2020-01-09
US10981904B2 (en) 2021-04-20
IL259510A (en) 2018-07-31
CO2018006928A2 (es) 2018-10-10
EA201891241A1 (ru) 2019-01-31
KR20180083942A (ko) 2018-07-23
AR106874A1 (es) 2018-02-28
US20190389853A1 (en) 2019-12-26
EP3383873B1 (en) 2022-03-09

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