CA3005516C - 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
CA3005516C
CA3005516C CA3005516A CA3005516A CA3005516C CA 3005516 C CA3005516 C CA 3005516C CA 3005516 A CA3005516 A CA 3005516A CA 3005516 A CA3005516 A CA 3005516A CA 3005516 C CA3005516 C CA 3005516C
Authority
CA
Canada
Prior art keywords
methoxy
thiadiazol
methylpyridazin
pyrrolidin
compound
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
CA3005516A
Other languages
English (en)
French (fr)
Other versions
CA3005516A1 (en
Inventor
Maurice Raymond Verschoyle Finlay
Johannes Wilhelmus Maria Nissink
Mark David Charles
James Matthew Wood
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 CA3005516A1 publication Critical patent/CA3005516A1/en
Application granted granted Critical
Publication of CA3005516C publication Critical patent/CA3005516C/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D417/00Heterocyclic 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
    • C07D417/14Heterocyclic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495Heterocyclic 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
    • A61K31/50Pyridazines; Hydrogenated pyridazines
    • A61K31/501Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/53Heterocyclic 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicinal Preparation (AREA)
CA3005516A 2015-11-30 2016-11-30 1,3,4-thiadiazole compounds and their use in treating cancer Active CA3005516C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562260787P 2015-11-30 2015-11-30
US62/260787 2015-11-30
PCT/EP2016/079251 WO2017093300A1 (en) 2015-11-30 2016-11-30 1,3,4-thiadiazole compounds and their use in treating cancer

Publications (2)

Publication Number Publication Date
CA3005516A1 CA3005516A1 (en) 2017-06-08
CA3005516C true CA3005516C (en) 2024-04-16

Family

ID=57421876

Family Applications (1)

Application Number Title Priority Date Filing Date
CA3005516A Active CA3005516C (en) 2015-11-30 2016-11-30 1,3,4-thiadiazole compounds and their use in treating cancer

Country Status (25)

Country Link
US (1) US9938265B2 (cg-RX-API-DMAC7.html)
EP (1) EP3383871B1 (cg-RX-API-DMAC7.html)
JP (1) JP6873132B2 (cg-RX-API-DMAC7.html)
KR (1) KR20180083412A (cg-RX-API-DMAC7.html)
CN (1) CN108349967B (cg-RX-API-DMAC7.html)
AR (1) AR106876A1 (cg-RX-API-DMAC7.html)
AU (1) AU2016363719B2 (cg-RX-API-DMAC7.html)
BR (1) BR112018010812A2 (cg-RX-API-DMAC7.html)
CA (1) CA3005516C (cg-RX-API-DMAC7.html)
CL (1) CL2018001408A1 (cg-RX-API-DMAC7.html)
CO (1) CO2018006929A2 (cg-RX-API-DMAC7.html)
DK (1) DK3383871T3 (cg-RX-API-DMAC7.html)
DO (1) DOP2018000134A (cg-RX-API-DMAC7.html)
EA (1) EA201891240A1 (cg-RX-API-DMAC7.html)
ES (1) ES2759940T3 (cg-RX-API-DMAC7.html)
IL (1) IL258644A (cg-RX-API-DMAC7.html)
MX (1) MX2018006528A (cg-RX-API-DMAC7.html)
NI (1) NI201800065A (cg-RX-API-DMAC7.html)
PE (1) PE20181450A1 (cg-RX-API-DMAC7.html)
PH (1) PH12018501132A1 (cg-RX-API-DMAC7.html)
SG (1) SG11201803813UA (cg-RX-API-DMAC7.html)
SV (1) SV2018005701A (cg-RX-API-DMAC7.html)
TN (1) TN2018000126A1 (cg-RX-API-DMAC7.html)
TW (1) TW201730188A (cg-RX-API-DMAC7.html)
WO (1) WO2017093300A1 (cg-RX-API-DMAC7.html)

Families Citing this family (5)

* 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
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
TW201733587A (zh) * 2015-11-30 2017-10-01 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
CN112888686B (zh) * 2018-10-16 2022-04-19 南京明德新药研发有限公司 噻二唑衍生物及其作为gls1抑制剂的应用
WO2025196446A1 (en) * 2024-03-22 2025-09-25 Sitryx Therapeutics Limited Thiadiazoles as glutaminase 1 inhibitors

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE377011T1 (de) * 1999-11-24 2007-11-15 Merck & Co Inc Gamma-hydroxy-2-(fluoralkylaminocarbonyl)-1- piperazinpentanamide als hiv-proteasehemmer
US6451828B1 (en) * 2000-08-10 2002-09-17 Elan Pharmaceuticals, Inc. Selective inhibition of glutaminase by bis-thiadiazoles
MY142655A (en) * 2003-06-12 2010-12-15 Euro Celtique Sa Therapeutic agents useful for treating pain
EP1828144A2 (en) * 2004-11-12 2007-09-05 OSI Pharmaceuticals, Inc. Integrin antagonists useful as anticancer agents
AU2010241084B2 (en) * 2009-04-20 2014-10-23 F. Hoffmann-La Roche Ag Proline derivatives as cathepsin inhibitors
SG11201402305WA (en) 2011-11-21 2014-06-27 Calithera Biosciences Inc Heterocyclic inhibitors of glutaminase
US10793535B2 (en) * 2012-11-16 2020-10-06 Calithera Biosciences, Inc. Heterocyclic glutaminase inhibitors
US9029531B2 (en) 2012-11-22 2015-05-12 Agios Pharmaceuticals, Inc. Compounds and their methods of use
CN105960405B (zh) * 2014-01-06 2021-02-19 理森制药股份公司 谷氨酰胺酶抑制剂
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
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
TW201733587A (zh) * 2015-11-30 2017-10-01 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

Also Published As

Publication number Publication date
MX2018006528A (es) 2019-05-15
ES2759940T8 (es) 2020-05-20
IL258644A (en) 2018-06-28
CO2018006929A2 (es) 2018-10-10
ES2759940T3 (es) 2020-05-12
NI201800065A (es) 2018-10-18
PH12018501132A1 (en) 2019-01-21
PE20181450A1 (es) 2018-09-12
DOP2018000134A (es) 2018-06-30
AU2016363719B2 (en) 2019-11-14
JP2019501134A (ja) 2019-01-17
TW201730188A (zh) 2017-09-01
EP3383871A1 (en) 2018-10-10
SV2018005701A (es) 2018-11-27
SG11201803813UA (en) 2018-06-28
EA201891240A1 (ru) 2018-11-30
JP6873132B2 (ja) 2021-05-19
TN2018000126A1 (en) 2019-10-04
DK3383871T3 (da) 2019-12-16
CL2018001408A1 (es) 2018-10-12
CA3005516A1 (en) 2017-06-08
US9938265B2 (en) 2018-04-10
WO2017093300A1 (en) 2017-06-08
AR106876A1 (es) 2018-02-28
CN108349967A (zh) 2018-07-31
KR20180083412A (ko) 2018-07-20
AU2016363719A8 (en) 2018-07-12
US20170152254A1 (en) 2017-06-01
EP3383871B1 (en) 2019-09-11
AU2016363719A1 (en) 2018-07-05
BR112018010812A2 (pt) 2018-11-27
CN108349967B (zh) 2022-02-15

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