DK3148994T3 - 1,3,4-thiadiazolforbindelser og deres anvendelse til behandling af cancer - Google Patents

1,3,4-thiadiazolforbindelser og deres anvendelse til behandling af cancer Download PDF

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Publication number
DK3148994T3
DK3148994T3 DK15726266.8T DK15726266T DK3148994T3 DK 3148994 T3 DK3148994 T3 DK 3148994T3 DK 15726266 T DK15726266 T DK 15726266T DK 3148994 T3 DK3148994 T3 DK 3148994T3
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amino
methoxy
acetamide
thiadiazol
pyridazin
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DK15726266.8T
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Maurice Raymond Verschoyle Finlay
Chukuemeka Tennyson Ekwuru
Mark David Charles
Piotr Antoni Raubo
Jonathan James Gordon Winter
Johannes Wilhelmus Maria Nissink
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Astrazeneca Ab
Cancer Research Tech Ltd
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    • 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
    • A61K31/41—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
    • A61K31/433—Thidiazoles
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
    • C07B59/002—Heterocyclic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/05—Isotopically modified compounds, e.g. labelled
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/13—Crystalline forms, e.g. polymorphs

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Claims (12)

1. Forbindelse med formel (I):
(I) eller et farmaceutisk acceptabelt salt deraf, hvor: Q er pyridazin-3-yl, 1,2,4-triazin-3-yl eller 1,2,4-triazin-6- yi; R er hydro, fluor eller methoxy; R1 er hydro, methoxy, difluormethoxy eller trifluormethoxy; og R2 er methyl eller ethyl.
2. Forbindelse med formel (I) eller et farmaceutisk acceptabelt salt deraf ifølge krav 1, hvor Q er pyridazin-3-yl eller 1,2,4-triazin-3-yl.
3. Forbindelse med formel (I) eller et farmaceutisk acceptabelt salt deraf ifølge krav 2, hvor Q er pyridazin-3- yl.
4. Forbindelse med formel (I) eller et farmaceutisk acceptabelt salt deraf ifølge et hvilket som helst af kravene 1 til 3, hvor R er hydro.
5. Forbindelse med formel (I) eller et farmaceutisk acceptabelt salt deraf ifølge et hvilket som helst af kravene 1 til 4, hvor R1 er hydro.
6. Forbindelse med formel (I) eller et farmaceutisk acceptabelt salt deraf ifølge et hvilket som helst af kravene 1 til 4, hvor R1 er methoxy, dif luormethoxy eller trifluormethoxy.
Ί. Forbindelse med formel (I) eller et farmaceutisk acceptabelt salt deraf ifølge krav 6, hvor R1 er methoxy.
8. Forbindelse med formel (I) eller et farmaceutisk acceptabelt salt deraf ifølge et hvilket som helst af kravene 1 til 7, hvor R2 er methyl.
9. Forbindelse med formel (I) eller et farmaceutisk acceptabelt salt deraf ifølge et hvilket som helst af kravene 1 til 7, hvor R2 er ethyl.
10. Forbindelse med formel (I) eller et farmaceutisk acceptabelt salt deraf ifølge krav 1, hvor forbindelsen er valgt fra gruppen, der består af: (2 S)-2-methoxy-2-phenyl-N-[5 —[[ (3R)-1-(1,2,4-triazin-3-yl) pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2R)-2-methoxy-2-phenyl-N-[5 —[[ (3R)-1-(1,2,4-triazin-3-yl) pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2S)-2-methoxy-2-phenyl-N-[5-[[(3R)-l-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2R)-2-methoxy-2-phenyl-N-[5-[[(3R)-l-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2 S)-2-methoxy-2-phenyl-N-[5 —[[ (3R)-1-(1,2,4-triazin-6-yl) pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2 S)-2-methoxy-2-(3-methoxyphenyl)-N-[5-[ (3R)-1-(1,2,4-triazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2R)-2-methoxy-2-(3-methoxyphenyl)-N-[5-[(3R)-1-(1,2,4-triazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2S)-2-methoxy-2-(3-methoxyphenyl)-N-[5-[(3R)-l-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2R)-2-methoxy-2-(3-methoxyphenyl)-N-[5-[(3R)-l-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2S)-2-[3-(difluormethoxy)phenyl]-2-methoxy-N-[5-[[(3R)-1-(l,2,4-triazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2R)-2-[3-(difluormethoxy)phenyl]-2-methoxy-N-[5-[[(3R)-1- (l,2,4-triazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2S)-2-[3-(difluormethoxy)phenyl]-2-methoxy-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2R)-2-[3-(difluormethoxy)phenyl]-2-methoxy-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2 S)-2-methoxy-N-[5-[[(3R)-1-(1,2,4-triazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]-2-[3-(trifluormethoxy)phenyl]acetamid; (2R)-2-methoxy-N-[5-[[(3R)-1-(1,2,4-triazin-3-yl)pyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]-2-[3-(trifluormethoxy)phenyl]acetamid; (2S)-2-methoxy-N-[5-[[(3N)-l-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]-2-[3-(trifluormethoxy)phenyl]acetamid; (2R)-2-methoxy-N-[5-[[(3R)-l-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]-2-[3-(trifluormethoxy)phenyl]acetamid; (2S)-2-ethoxy-2-phenyl-N-[5-[[(3R)-l-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2S)-2-methoxy-2-(4-methoxyphenyl)-N-[5-[[(3R)-l-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2R)-2-ethoxy-2-phenyl-N-[5-[[(3R)-l-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2S)-2- (4-fluorphenyl)-2-methoxy-N-[5-[[ (3R)-l-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2R)-2-(4-fluorphenyl)-2-methoxy-N-[5-[[(3R)-l-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2S)-2-ethoxy-2-(4-fluorphenyl)-N-[5-[[(3R)-l-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2R)-2-ethoxy-2-(4-fluorphenyl)-N-[5-[[(3R)-l-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2S)-2-(4-fluor-3-methoxy-phenyl)-2-methoxy-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2R)-2-(4-fluor-3-methoxy-phenyl)-2-methoxy-N-[5-[[(3R)-1- pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2S)-2-[3-(difluormethoxy)phenyl]-2-ethoxy-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2R)-2-[3-(difluormethoxy)phenyl]-2-ethoxy-N-[5-[[(3R)-1-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]acetamid; (2S)-2-ethoxy-N-[5-[[(3R)-l-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]-2-[3-(trifluormethoxy)phenyl]acetamid; og (2R)-2-ethoxy-N-[5-[[(3R)-l-pyridazin-3-ylpyrrolidin-3-yl]amino]-1,3,4-thiadiazol-2-yl]-2-[3-(trifluormethoxy)phenyl]acetamid.
11. Farmaceutisk sammensætning, der omfatter en forbindelse med formel (I) eller et farmaceutisk acceptabelt salt deraf ifølge et hvilket som helst af kravene 1 til 10 og mindst ét farmaceutisk acceptabelt fortyndingsmiddel eller bæremateriale.
12. Forbindelse med formel (I) eller et farmaceutisk acceptabelt salt deraf ifølge et hvilket som helst af kravene 1 til 10 til anvendelse til terapi.
13. Forbindelse med formel (I) eller et farmaceutisk acceptabelt salt deraf ifølge et hvilket som helst af kravene 1 til 10 til anvendelse til behandling af cancer.
DK15726266.8T 2014-05-30 2015-05-27 1,3,4-thiadiazolforbindelser og deres anvendelse til behandling af cancer DK3148994T3 (da)

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GBGB1409624.2A GB201409624D0 (en) 2014-05-30 2014-05-30 1,3,4-thiadiazole compounds and their use in treating cancer
PCT/GB2015/051537 WO2015181539A1 (en) 2014-05-30 2015-05-27 1, 3, 4-thiadiazole compounds and their use in treating cancer

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EP (1) EP3148994B1 (da)
JP (1) JP6538830B2 (da)
KR (1) KR20170005875A (da)
CN (1) CN106795150B (da)
AP (1) AP2016009578A0 (da)
AR (1) AR100694A1 (da)
AU (1) AU2015265703B2 (da)
BR (1) BR112016028002B1 (da)
CA (1) CA2949598C (da)
CL (1) CL2016003074A1 (da)
CR (1) CR20160558A (da)
CY (1) CY1120836T1 (da)
DK (1) DK3148994T3 (da)
DO (1) DOP2016000308A (da)
EA (1) EA030937B1 (da)
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GB (1) GB201409624D0 (da)
GT (1) GT201600250A (da)
HR (1) HRP20181490T1 (da)
HU (1) HUE039879T2 (da)
IL (1) IL249020B (da)
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MX (1) MX2016015738A (da)
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PE (1) PE20170148A1 (da)
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SM (1) SMT201800516T1 (da)
SV (1) SV2016005330A (da)
TN (1) TN2016000511A1 (da)
TW (1) TWI693220B (da)
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TW201730188A (zh) * 2015-11-30 2017-09-01 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
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KR102934231B1 (ko) * 2019-03-05 2026-03-06 아스트라제네카 아베 항암제로 유용한 융합 삼환식 화합물
CN121532182A (zh) * 2023-05-10 2026-02-13 里尔治疗股份有限公司 谷氨酰胺酶的小分子抑制剂
CN116854582B (zh) * 2023-07-10 2025-08-29 泰州葛林美克医药科技有限公司 一种对映纯α-甲氧基苯乙酸的制备方法
CN117003745B (zh) * 2023-07-20 2024-06-07 南京市第一医院 Gls1/hdac双靶点抑制剂及其合成方法和应用
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PT3148994T (pt) 2018-10-22
ES2688396T3 (es) 2018-11-02
EA030937B1 (ru) 2018-10-31
US10040788B2 (en) 2018-08-07
AU2015265703A1 (en) 2016-12-15
HUE039879T2 (hu) 2019-02-28
DOP2016000308A (es) 2017-03-15
TW201609720A (zh) 2016-03-16
US20170197954A1 (en) 2017-07-13
UY36145A (es) 2016-01-08
TN2016000511A1 (en) 2018-04-04
CA2949598A1 (en) 2015-12-03
AP2016009578A0 (en) 2016-11-30
CY1120836T1 (el) 2019-12-11
CN106795150B (zh) 2019-10-15
TWI693220B (zh) 2020-05-11
IL249020B (en) 2020-11-30
NZ726790A (en) 2017-11-24
CR20160558A (es) 2017-09-01
EP3148994B1 (en) 2018-07-11
AR100694A1 (es) 2016-10-26
PL3148994T3 (pl) 2019-04-30
WO2015181539A1 (en) 2015-12-03
SV2016005330A (es) 2017-06-07
SG11201609880QA (en) 2016-12-29
SMT201800516T1 (it) 2018-11-09
BR112016028002A2 (da) 2017-08-22
MY192861A (en) 2022-09-13
RS57876B1 (sr) 2018-12-31
CL2016003074A1 (es) 2017-04-28
EA201692260A1 (ru) 2017-06-30
GT201600250A (es) 2019-06-10
MX2016015738A (es) 2017-02-27
JP2017516859A (ja) 2017-06-22
GB201409624D0 (en) 2014-07-16
CA2949598C (en) 2022-08-09
NI201600176A (es) 2017-08-25
LT3148994T (lt) 2018-11-26
IL249020A0 (en) 2017-01-31
HRP20181490T1 (hr) 2019-01-11
SI3148994T1 (sl) 2018-12-31
JP6538830B2 (ja) 2019-07-03
PH12016502394A1 (en) 2017-02-20
KR20170005875A (ko) 2017-01-16
PE20170148A1 (es) 2017-04-05
US20180305349A1 (en) 2018-10-25
US10294221B2 (en) 2019-05-21
BR112016028002B1 (pt) 2022-09-27
AU2015265703B2 (en) 2017-12-07
CN106795150A (zh) 2017-05-31
EP3148994A1 (en) 2017-04-05

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