EA030646B1 - Соединения и способы их применения - Google Patents
Соединения и способы их применения Download PDFInfo
- Publication number
- EA030646B1 EA030646B1 EA201590987A EA201590987A EA030646B1 EA 030646 B1 EA030646 B1 EA 030646B1 EA 201590987 A EA201590987 A EA 201590987A EA 201590987 A EA201590987 A EA 201590987A EA 030646 B1 EA030646 B1 EA 030646B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- compound
- bis
- diyl
- pharmaceutically acceptable
- acceptable salt
- Prior art date
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- -1 -OH Chemical group 0.000 claims description 279
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 84
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- RVAVJTWTLZIHTJ-UHFFFAOYSA-N methyl 2-[2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-1,3-thiazol-4-yl]acetate Chemical compound COC(=O)CC1=CSC(N(C)C(=O)OC(C)(C)C)=N1 RVAVJTWTLZIHTJ-UHFFFAOYSA-N 0.000 description 1
- NFURJCZUQRMWFZ-UHFFFAOYSA-N methyl 2-[3-(3,3-difluoroazetidin-1-yl)phenyl]acetate Chemical compound COC(=O)CC1=CC=CC(N2CC(F)(F)C2)=C1 NFURJCZUQRMWFZ-UHFFFAOYSA-N 0.000 description 1
- MSPVJLQSTROFGA-UHFFFAOYSA-N methyl 2-[3-(azetidin-1-yl)phenyl]acetate Chemical compound COC(=O)CC1=CC=CC(N2CCC2)=C1 MSPVJLQSTROFGA-UHFFFAOYSA-N 0.000 description 1
- BVGHSPDEDKRWGG-UHFFFAOYSA-N methyl 2-[3-(cyclopropylamino)phenyl]acetate Chemical compound COC(=O)CC1=CC=CC(NC2CC2)=C1 BVGHSPDEDKRWGG-UHFFFAOYSA-N 0.000 description 1
- QGNULBBSPMJDEX-UHFFFAOYSA-N methyl 2-[3-(dimethylamino)pyridin-2-yl]acetate Chemical compound COC(=O)CC1=NC=CC=C1N(C)C QGNULBBSPMJDEX-UHFFFAOYSA-N 0.000 description 1
- QYHPSSAIUSMMOK-UHFFFAOYSA-N methyl 2-[3-(ethylamino)phenyl]acetate Chemical compound CCNC1=CC=CC(CC(=O)OC)=C1 QYHPSSAIUSMMOK-UHFFFAOYSA-N 0.000 description 1
- AKDJSSHOMUXMDO-UHFFFAOYSA-N methyl 2-[3-(hydroxymethyl)phenyl]acetate Chemical compound COC(=O)CC1=CC=CC(CO)=C1 AKDJSSHOMUXMDO-UHFFFAOYSA-N 0.000 description 1
- UMLCXALUSHYMHG-UHFFFAOYSA-N methyl 2-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]phenyl]acetate Chemical compound COC(=O)CC1=CC=CC(CNC(=O)OC(C)(C)C)=C1 UMLCXALUSHYMHG-UHFFFAOYSA-N 0.000 description 1
- WULXTSYCDARSGC-UHFFFAOYSA-N methyl 2-[4-(3,3-difluoroazetidin-1-yl)pyridin-2-yl]acetate Chemical compound C1=NC(CC(=O)OC)=CC(N2CC(F)(F)C2)=C1 WULXTSYCDARSGC-UHFFFAOYSA-N 0.000 description 1
- QNAJJWDKBDJGPT-UHFFFAOYSA-N methyl 2-[4-(3-hydroxyazetidin-1-yl)pyridin-2-yl]acetate Chemical compound C1=NC(CC(=O)OC)=CC(N2CC(O)C2)=C1 QNAJJWDKBDJGPT-UHFFFAOYSA-N 0.000 description 1
- HHNJODYIVMUMDY-UHFFFAOYSA-N methyl 2-[5-(difluoromethoxy)pyridin-2-yl]acetate Chemical compound COC(=O)CC1=CC=C(OC(F)F)C=N1 HHNJODYIVMUMDY-UHFFFAOYSA-N 0.000 description 1
- MQZUNOVVHOYZIO-UHFFFAOYSA-N methyl 2-[5-(dimethylamino)pyridin-2-yl]acetate Chemical compound COC(=O)CC1=CC=C(N(C)C)C=N1 MQZUNOVVHOYZIO-UHFFFAOYSA-N 0.000 description 1
- ZAQMXPNHPFCXBI-UHFFFAOYSA-N methyl 2-[5-(dimethylcarbamoyl)pyridin-2-yl]acetate Chemical compound COC(=O)CC1=CC=C(C(=O)N(C)C)C=N1 ZAQMXPNHPFCXBI-UHFFFAOYSA-N 0.000 description 1
- JDSWJCSKJZEXMM-UHFFFAOYSA-N methyl 2-[5-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyridin-2-yl]acetate Chemical compound COC(=O)CC1=CC=C(CNC(=O)OC(C)(C)C)C=N1 JDSWJCSKJZEXMM-UHFFFAOYSA-N 0.000 description 1
- VHBKPOKJSMXUDB-UHFFFAOYSA-N methyl 2-[5-[tert-butyl(dimethyl)silyl]oxypyridin-2-yl]acetate Chemical compound COC(=O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=N1 VHBKPOKJSMXUDB-UHFFFAOYSA-N 0.000 description 1
- IWRPHUBFVVHWPG-UHFFFAOYSA-N methyl 2-[6-(3,3-difluoroazetidin-1-yl)pyridin-3-yl]acetate Chemical compound N1=CC(CC(=O)OC)=CC=C1N1CC(F)(F)C1 IWRPHUBFVVHWPG-UHFFFAOYSA-N 0.000 description 1
- YBUSEKHEULAKDH-UHFFFAOYSA-N methyl 2-[6-(3-hydroxyazetidin-1-yl)pyridin-2-yl]acetate Chemical compound COC(=O)CC1=CC=CC(N2CC(O)C2)=N1 YBUSEKHEULAKDH-UHFFFAOYSA-N 0.000 description 1
- ATYJHKTWLVGXJK-UHFFFAOYSA-N methyl 2-[6-(3-methoxyazetidin-1-yl)pyridin-2-yl]acetate Chemical compound C1C(OC)CN1C1=CC=CC(CC(=O)OC)=N1 ATYJHKTWLVGXJK-UHFFFAOYSA-N 0.000 description 1
- GJUIRRZPFMZFJU-UHFFFAOYSA-N methyl 2-[6-(azetidin-1-yl)pyridin-2-yl]acetate Chemical compound COC(=O)CC1=CC=CC(N2CCC2)=N1 GJUIRRZPFMZFJU-UHFFFAOYSA-N 0.000 description 1
- ORAKNQSHWMHCEY-UHFFFAOYSA-N methyl 2-pyridin-2-ylacetate Chemical compound COC(=O)CC1=CC=CC=N1 ORAKNQSHWMHCEY-UHFFFAOYSA-N 0.000 description 1
- ZDUBLLCAMMIGFH-UHFFFAOYSA-N methyl 2-pyrimidin-2-ylacetate Chemical compound COC(=O)CC1=NC=CC=N1 ZDUBLLCAMMIGFH-UHFFFAOYSA-N 0.000 description 1
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- KLCWZHVQXHPZOG-YUMQZZPRSA-N n-[5-[(1s,3s)-3-(5-amino-1,3,4-thiadiazol-2-yl)cyclohexyl]-1,3,4-thiadiazol-2-yl]propanamide Chemical compound S1C(NC(=O)CC)=NN=C1[C@@H]1C[C@@H](C=2SC(N)=NN=2)CCC1 KLCWZHVQXHPZOG-YUMQZZPRSA-N 0.000 description 1
- QROKOTBWFZITJZ-UHFFFAOYSA-N n-pyridin-2-ylacetamide Chemical compound CC(=O)NC1=CC=CC=N1 QROKOTBWFZITJZ-UHFFFAOYSA-N 0.000 description 1
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- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
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- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
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- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- MRTAVLDNYYEJHK-UHFFFAOYSA-M sodium;2-chloro-2,2-difluoroacetate Chemical compound [Na+].[O-]C(=O)C(F)(F)Cl MRTAVLDNYYEJHK-UHFFFAOYSA-M 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
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- BBGGVTGEGMNWSK-UHFFFAOYSA-N tert-butyl 4-[3-(2-methoxy-2-oxoethyl)phenyl]piperidine-1-carboxylate Chemical compound COC(=O)CC1=CC=CC(C2CCN(CC2)C(=O)OC(C)(C)C)=C1 BBGGVTGEGMNWSK-UHFFFAOYSA-N 0.000 description 1
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
- 239000012414 tert-butyl nitrite Substances 0.000 description 1
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 1
- MHXBHWLGRWOABW-UHFFFAOYSA-N tetradecyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCCCC MHXBHWLGRWOABW-UHFFFAOYSA-N 0.000 description 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
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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
- A61K31/41—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
- C07D285/01—Five-membered rings
- C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
- C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
- C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
- C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
- C07D285/135—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/CN2012/085023 WO2014079011A1 (en) | 2012-11-22 | 2012-11-22 | Heterocyclic compounds for inhibiting glutaminase and their methods of use |
| PCT/CN2013/000294 WO2014079136A1 (en) | 2012-11-22 | 2013-03-15 | Compounds, pharmaceutical compositions and uses as glutaminase inhibitors for treating cancers thereof |
| PCT/CN2013/001428 WO2014079150A1 (en) | 2012-11-22 | 2013-11-21 | Compounds and their methods of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201590987A1 EA201590987A1 (ru) | 2015-12-30 |
| EA030646B1 true EA030646B1 (ru) | 2018-09-28 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201590987A EA030646B1 (ru) | 2012-11-22 | 2013-11-21 | Соединения и способы их применения |
| EA201890754A EA201890754A1 (ru) | 2012-11-22 | 2013-11-21 | Соединения и способы их применения |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201890754A EA201890754A1 (ru) | 2012-11-22 | 2013-11-21 | Соединения и способы их применения |
Country Status (36)
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8604016B2 (en) | 2011-11-21 | 2013-12-10 | Calithera Biosciences Inc. | Heterocyclic inhibitors of glutaminase |
| JP6275153B2 (ja) | 2012-11-16 | 2018-02-07 | キャリセラ バイオサイエンシーズ, インコーポレイテッド | ヘテロ環式グルタミナーゼ阻害剤 |
| MX369691B (es) | 2012-11-21 | 2019-11-19 | Agios Pharmaceuticals Inc | Inhibidores de glutaminasa y métodos de empleo. |
| WO2014079011A1 (en) | 2012-11-22 | 2014-05-30 | Agios Pharmaceuticals, Inc. | Heterocyclic compounds for inhibiting glutaminase and their methods of use |
| CA2892817A1 (en) * | 2012-12-03 | 2014-06-12 | Calithera Biosciences Inc. | Treatment of cancer with heterocyclic inhibitors of glutaminase |
| JP6437452B2 (ja) | 2013-01-14 | 2018-12-12 | インサイト・ホールディングス・コーポレイションIncyte Holdings Corporation | Pimキナーゼ阻害剤として有用な二環式芳香族カルボキサミド化合物 |
| LT2945939T (lt) | 2013-01-15 | 2020-07-27 | Incyte Holdings Corporation | Triazolkarboksamidai ir piridinkarboksamido junginiai, naudotini kaip pim kinazės inhibitoriai |
| EP3036238A1 (en) | 2013-08-23 | 2016-06-29 | Incyte Corporation | Furo- and thieno-pyridine carboxamide compounds useful as pim kinase inhibitors |
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