AU2016361834B2 - 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 PDFInfo
- Publication number
- AU2016361834B2 AU2016361834B2 AU2016361834A AU2016361834A AU2016361834B2 AU 2016361834 B2 AU2016361834 B2 AU 2016361834B2 AU 2016361834 A AU2016361834 A AU 2016361834A AU 2016361834 A AU2016361834 A AU 2016361834A AU 2016361834 B2 AU2016361834 B2 AU 2016361834B2
- Authority
- AU
- Australia
- Prior art keywords
- amino
- pyridazin
- acetamide
- thiadiazol
- phenyl
- 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
Links
- BDBFPNBOFLDJND-SSDOTTSWSA-N Nc1nnc(N[C@H](CC2)CN2c2nnccc2)[s]1 Chemical compound Nc1nnc(N[C@H](CC2)CN2c2nnccc2)[s]1 BDBFPNBOFLDJND-SSDOTTSWSA-N 0.000 description 2
- VYAQCWUQXIXCIX-UHFFFAOYSA-N CC(Oc1cc(C(C(O)=O)Br)ccc1)F Chemical compound CC(Oc1cc(C(C(O)=O)Br)ccc1)F VYAQCWUQXIXCIX-UHFFFAOYSA-N 0.000 description 1
- ZLUNIMIQWCCCHH-OMOCHNIRSA-N CN(C)[C@@H](C(Nc1nnc(NC(CC2)CN2c2cccnn2)[s]1)=O)c(cc1)ccc1F Chemical compound CN(C)[C@@H](C(Nc1nnc(NC(CC2)CN2c2cccnn2)[s]1)=O)c(cc1)ccc1F ZLUNIMIQWCCCHH-OMOCHNIRSA-N 0.000 description 1
- VOPBRZXKPSPMAY-VQIMIIECSA-N COc1cc([C@H](C(Nc2nnc(N[C@H](CC3)CN3c3cccnn3)[s]2)=O)N2CCC2)ccc1 Chemical compound COc1cc([C@H](C(Nc2nnc(N[C@H](CC3)CN3c3cccnn3)[s]2)=O)N2CCC2)ccc1 VOPBRZXKPSPMAY-VQIMIIECSA-N 0.000 description 1
- AXRVWVBJEIBSRD-NSHDSACASA-N COc1cccc([C@@H](C(N)=O)N2CCC2)c1 Chemical compound COc1cccc([C@@H](C(N)=O)N2CCC2)c1 AXRVWVBJEIBSRD-NSHDSACASA-N 0.000 description 1
- OTZBYWQLUIYFAU-GXTWGEPZSA-N C[C@H](C(Nc1nnc(N[C@H](CC2)CN2c2nnccc2)[s]1)=O)c1cccc(OC(F)F)c1 Chemical compound C[C@H](C(Nc1nnc(N[C@H](CC2)CN2c2nnccc2)[s]1)=O)c1cccc(OC(F)F)c1 OTZBYWQLUIYFAU-GXTWGEPZSA-N 0.000 description 1
- CSNOMEYXRFRNOF-DZGCQCFKSA-N C[C@H](C(Nc1nnc(N[C@H](CC2)CN2c2nnccc2)[s]1)=O)c1ccccc1 Chemical compound C[C@H](C(Nc1nnc(N[C@H](CC2)CN2c2nnccc2)[s]1)=O)c1ccccc1 CSNOMEYXRFRNOF-DZGCQCFKSA-N 0.000 description 1
- JGRRPMNEWJNJGZ-CRAIPNDOSA-N O=C([C@@H](c1cccc(OC(F)F)c1)N1CCC1)Nc1nnc(N[C@H](CC2)CN2c2nnccc2)[s]1 Chemical compound O=C([C@@H](c1cccc(OC(F)F)c1)N1CCC1)Nc1nnc(N[C@H](CC2)CN2c2nnccc2)[s]1 JGRRPMNEWJNJGZ-CRAIPNDOSA-N 0.000 description 1
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
- A61K31/41—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
- 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
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562260784P | 2015-11-30 | 2015-11-30 | |
| US62/260,784 | 2015-11-30 | ||
| PCT/EP2016/079253 WO2017093301A1 (en) | 2015-11-30 | 2016-11-30 | 1,3,4-thiadiazole compounds and their use in treating cancer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2016361834A1 AU2016361834A1 (en) | 2018-07-12 |
| AU2016361834B2 true AU2016361834B2 (en) | 2019-11-14 |
Family
ID=57460503
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2016361834A Active AU2016361834B2 (en) | 2015-11-30 | 2016-11-30 | 1,3,4-thiadiazole compounds and their use in treating cancer |
Country Status (28)
| Country | Link |
|---|---|
| US (1) | US10040789B2 (enExample) |
| EP (1) | EP3383872B1 (enExample) |
| JP (1) | JP6821680B2 (enExample) |
| KR (1) | KR20180083411A (enExample) |
| CN (1) | CN108349965B (enExample) |
| AR (1) | AR106875A1 (enExample) |
| AU (1) | AU2016361834B2 (enExample) |
| BR (1) | BR112018008330B1 (enExample) |
| CA (1) | CA3005517C (enExample) |
| CL (1) | CL2018001409A1 (enExample) |
| CO (1) | CO2018006930A2 (enExample) |
| DK (1) | DK3383872T3 (enExample) |
| DO (1) | DOP2018000135A (enExample) |
| EA (1) | EA035519B9 (enExample) |
| ES (1) | ES2796562T3 (enExample) |
| IL (1) | IL259508A (enExample) |
| MX (1) | MX2018006483A (enExample) |
| MY (1) | MY195680A (enExample) |
| NI (1) | NI201800063A (enExample) |
| NZ (1) | NZ743699A (enExample) |
| PE (1) | PE20181522A1 (enExample) |
| PH (1) | PH12018501133A1 (enExample) |
| SG (1) | SG11201803808VA (enExample) |
| SV (1) | SV2018005700A (enExample) |
| TN (1) | TN2018000118A1 (enExample) |
| TW (1) | TW201731511A (enExample) |
| WO (1) | WO2017093301A1 (enExample) |
| ZA (1) | ZA201804361B (enExample) |
Families Citing this family (7)
| 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 |
| US10323028B2 (en) | 2015-11-30 | 2019-06-18 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| 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 |
| CN114560855B (zh) * | 2021-03-26 | 2023-05-23 | 成都苑东生物制药股份有限公司 | 环烷基甲酰胺类衍生物、其制备方法及用途 |
| WO2025196447A1 (en) | 2024-03-22 | 2025-09-25 | Sitryx Therapeutics Limited | Thiadiazoles as glutaminase 1 inhibitors |
| WO2025196446A1 (en) | 2024-03-22 | 2025-09-25 | Sitryx Therapeutics Limited | Thiadiazoles as glutaminase 1 inhibitors |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013078123A1 (en) * | 2011-11-21 | 2013-05-30 | Calithera Biosciences Inc. | Heterocyclic inhibitors of glutaminase |
| US20140142081A1 (en) * | 2012-11-22 | 2014-05-22 | Agios Pharmaceuticals, Inc | Compounds and their methods of use |
| WO2015181539A1 (en) * | 2014-05-30 | 2015-12-03 | Astrazeneca Ab | 1, 3, 4-thiadiazole compounds and their use in treating cancer |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20160100407A (ko) | 2014-01-06 | 2016-08-23 | 리젠 파마슈티컬스 소시에떼 아노님 | 신규한 글루타미나제의 저해제 |
| US9938265B2 (en) * | 2015-11-30 | 2018-04-10 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
| US10323028B2 (en) * | 2015-11-30 | 2019-06-18 | Astrazeneca Ab | 1,3,4-thiadiazole compounds and their use in treating cancer |
-
2016
- 2016-11-29 TW TW105139334A patent/TW201731511A/zh unknown
- 2016-11-29 US US15/362,989 patent/US10040789B2/en active Active
- 2016-11-30 SG SG11201803808VA patent/SG11201803808VA/en unknown
- 2016-11-30 KR KR1020187017163A patent/KR20180083411A/ko not_active Withdrawn
- 2016-11-30 TN TNP/2018/000118A patent/TN2018000118A1/en unknown
- 2016-11-30 AR ARP160103664A patent/AR106875A1/es unknown
- 2016-11-30 MY MYPI2018702070A patent/MY195680A/en unknown
- 2016-11-30 EP EP16805078.9A patent/EP3383872B1/en active Active
- 2016-11-30 ES ES16805078T patent/ES2796562T3/es active Active
- 2016-11-30 WO PCT/EP2016/079253 patent/WO2017093301A1/en not_active Ceased
- 2016-11-30 NZ NZ743699A patent/NZ743699A/en unknown
- 2016-11-30 BR BR112018008330-5A patent/BR112018008330B1/pt active IP Right Grant
- 2016-11-30 PE PE2018001012A patent/PE20181522A1/es unknown
- 2016-11-30 DK DK16805078.9T patent/DK3383872T3/da active
- 2016-11-30 JP JP2018527201A patent/JP6821680B2/ja active Active
- 2016-11-30 EA EA201891239A patent/EA035519B9/ru not_active IP Right Cessation
- 2016-11-30 MX MX2018006483A patent/MX2018006483A/es unknown
- 2016-11-30 CN CN201680067210.XA patent/CN108349965B/zh active Active
- 2016-11-30 CA CA3005517A patent/CA3005517C/en active Active
- 2016-11-30 AU AU2016361834A patent/AU2016361834B2/en active Active
-
2018
- 2018-05-22 IL IL259508A patent/IL259508A/en active IP Right Grant
- 2018-05-24 CL CL2018001409A patent/CL2018001409A1/es unknown
- 2018-05-29 DO DO2018000135A patent/DOP2018000135A/es unknown
- 2018-05-29 NI NI201800063A patent/NI201800063A/es unknown
- 2018-05-29 PH PH12018501133A patent/PH12018501133A1/en unknown
- 2018-05-29 SV SV2018005700A patent/SV2018005700A/es unknown
- 2018-06-28 ZA ZA2018/04361A patent/ZA201804361B/en unknown
- 2018-06-29 CO CONC2018/0006930A patent/CO2018006930A2/es unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013078123A1 (en) * | 2011-11-21 | 2013-05-30 | Calithera Biosciences Inc. | Heterocyclic inhibitors of glutaminase |
| US20140142081A1 (en) * | 2012-11-22 | 2014-05-22 | Agios Pharmaceuticals, Inc | Compounds and their methods of use |
| WO2015181539A1 (en) * | 2014-05-30 | 2015-12-03 | Astrazeneca Ab | 1, 3, 4-thiadiazole compounds and their use in treating cancer |
Non-Patent Citations (1)
| Title |
|---|
| AJIT G. THOMAS ET AL, "Small molecule glutaminase inhibitors block glutamate release from stimulated microglia", BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2014, vol. 443(1), pages 32 - 36 * |
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) |