ES2587939T3 - Derivados de pirrolotriazinona - Google Patents
Derivados de pirrolotriazinona Download PDFInfo
- Publication number
- ES2587939T3 ES2587939T3 ES13714859.9T ES13714859T ES2587939T3 ES 2587939 T3 ES2587939 T3 ES 2587939T3 ES 13714859 T ES13714859 T ES 13714859T ES 2587939 T3 ES2587939 T3 ES 2587939T3
- Authority
- ES
- Spain
- Prior art keywords
- denotes
- triazin
- pyrrolo
- hal
- benzyl
- 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.)
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- BEBRHYJBTAMGRW-UHFFFAOYSA-N pyrrolo[3,2-d]triazin-4-one Chemical class O=C1N=NN=C2C=CN=C12 BEBRHYJBTAMGRW-UHFFFAOYSA-N 0.000 title 1
- -1 tetrahydroimidazolyl Chemical group 0.000 claims abstract description 29
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 3
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims abstract 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims abstract 2
- 239000012453 solvate Substances 0.000 claims abstract 2
- AVEFNYIOACXTPD-UHFFFAOYSA-N 2-cyclohexyl-1h-pyrrolo[2,1-f][1,2,4]triazin-4-one Chemical compound N1N2C=CC=C2C(=O)N=C1C1CCCCC1 AVEFNYIOACXTPD-UHFFFAOYSA-N 0.000 claims description 2
- QNLQDXLNFJEHGG-UHFFFAOYSA-N 2-[4-(2-hydroxypropan-2-yl)phenyl]-6-methyl-1h-pyrrolo[2,1-f][1,2,4]triazin-4-one Chemical compound C1=C(C)C=C(C(N=2)=O)N1NC=2C1=CC=C(C(C)(C)O)C=C1 QNLQDXLNFJEHGG-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 101100406879 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) par-2 gene Proteins 0.000 abstract 5
- 125000002393 azetidinyl group Chemical group 0.000 abstract 3
- 125000002757 morpholinyl group Chemical group 0.000 abstract 3
- 125000003386 piperidinyl group Chemical group 0.000 abstract 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 abstract 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 abstract 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 abstract 2
- 125000002541 furyl group Chemical group 0.000 abstract 2
- 125000002883 imidazolyl group Chemical group 0.000 abstract 2
- 125000005945 imidazopyridyl group Chemical group 0.000 abstract 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 abstract 2
- 125000001041 indolyl group Chemical group 0.000 abstract 2
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 abstract 2
- 125000000842 isoxazolyl group Chemical group 0.000 abstract 2
- 125000001715 oxadiazolyl group Chemical group 0.000 abstract 2
- 125000002971 oxazolyl group Chemical group 0.000 abstract 2
- 125000004193 piperazinyl group Chemical group 0.000 abstract 2
- 125000003226 pyrazolyl group Chemical group 0.000 abstract 2
- 125000002098 pyridazinyl group Chemical group 0.000 abstract 2
- 125000004076 pyridyl group Chemical group 0.000 abstract 2
- 125000000714 pyrimidinyl group Chemical group 0.000 abstract 2
- 125000000168 pyrrolyl group Chemical group 0.000 abstract 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract 2
- 125000003831 tetrazolyl group Chemical group 0.000 abstract 2
- 125000000335 thiazolyl group Chemical group 0.000 abstract 2
- 125000001544 thienyl group Chemical group 0.000 abstract 2
- 125000001425 triazolyl group Chemical group 0.000 abstract 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 abstract 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 abstract 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 abstract 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 abstract 1
- 125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 abstract 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 abstract 1
- 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 abstract 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 abstract 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000005493 quinolyl group Chemical group 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 125000005942 tetrahydropyridyl group Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 230000006907 apoptotic process Effects 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 238000013459 approach Methods 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003814 drug Substances 0.000 description 6
- FABUFPQFXZVHFB-CFWQTKTJSA-N ixabepilone Chemical compound C/C([C@@H]1C[C@@H]2O[C@]2(C)CCC[C@@H]([C@@H]([C@H](C)C(=O)C(C)(C)[C@H](O)CC(=O)N1)O)C)=C\C1=CSC(C)=N1 FABUFPQFXZVHFB-CFWQTKTJSA-N 0.000 description 6
- 229960002014 ixabepilone Drugs 0.000 description 6
- XKJMBINCVNINCA-UHFFFAOYSA-N Alfalone Chemical compound CON(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XKJMBINCVNINCA-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- RJURFGZVJUQBHK-UHFFFAOYSA-N actinomycin D Natural products CC1OC(=O)C(C(C)C)N(C)C(=O)CN(C)C(=O)C2CCCN2C(=O)C(C(C)C)NC(=O)C1NC(=O)C1=C(N)C(=O)C(C)=C2OC(C(C)=CC=C3C(=O)NC4C(=O)NC(C(N5CCCC5C(=O)N(C)CC(=O)N(C)C(C(C)C)C(=O)OC4C)=O)C(C)C)=C3N=C21 RJURFGZVJUQBHK-UHFFFAOYSA-N 0.000 description 4
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 4
- 125000004185 ester group Chemical group 0.000 description 4
- 235000019439 ethyl acetate Nutrition 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 238000004949 mass spectrometry Methods 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 108010006654 Bleomycin Proteins 0.000 description 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
- 108090000695 Cytokines Proteins 0.000 description 3
- 102000004127 Cytokines Human genes 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- KQYGMURBTJPBPQ-UHFFFAOYSA-L disodium;2-(2-sulfonatoethyldisulfanyl)ethanesulfonate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)CCSSCCS([O-])(=O)=O KQYGMURBTJPBPQ-UHFFFAOYSA-L 0.000 description 3
- OFDNQWIFNXBECV-VFSYNPLYSA-N dolastatin 10 Chemical compound CC(C)[C@H](N(C)C)C(=O)N[C@@H](C(C)C)C(=O)N(C)[C@@H]([C@@H](C)CC)[C@H](OC)CC(=O)N1CCC[C@H]1[C@H](OC)[C@@H](C)C(=O)N[C@H](C=1SC=CN=1)CC1=CC=CC=C1 OFDNQWIFNXBECV-VFSYNPLYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 3
- IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 description 2
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 2
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Oncology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12003445 | 2012-05-04 | ||
| EP12003445 | 2012-05-04 | ||
| PCT/EP2013/001026 WO2013164061A1 (en) | 2012-05-04 | 2013-04-06 | Pyrrolotriazinone derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2587939T3 true ES2587939T3 (es) | 2016-10-27 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES13714859.9T Active ES2587939T3 (es) | 2012-05-04 | 2013-04-06 | Derivados de pirrolotriazinona |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US9174995B2 (https=) |
| EP (1) | EP2844659B1 (https=) |
| JP (1) | JP6097820B2 (https=) |
| KR (1) | KR20150006873A (https=) |
| CN (1) | CN104271580B (https=) |
| AR (1) | AR090896A1 (https=) |
| AU (1) | AU2013257018B2 (https=) |
| CA (1) | CA2872334C (https=) |
| EA (1) | EA027628B1 (https=) |
| ES (1) | ES2587939T3 (https=) |
| HR (1) | HRP20161033T1 (https=) |
| HU (1) | HUE028325T2 (https=) |
| IL (1) | IL235414A (https=) |
| MX (1) | MX357502B (https=) |
| PL (1) | PL2844659T3 (https=) |
| PT (1) | PT2844659T (https=) |
| RS (1) | RS55062B1 (https=) |
| SG (1) | SG11201406997WA (https=) |
| SI (1) | SI2844659T1 (https=) |
| WO (1) | WO2013164061A1 (https=) |
| ZA (1) | ZA201408876B (https=) |
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| WO2013132253A1 (en) | 2012-03-07 | 2013-09-12 | Institute Of Cancer Research: Royal Cancer Hospital (The) | 3-aryl-5-substituted-isoquinolin-1-one compounds and their therapeutic use |
| EP3044221B1 (en) | 2013-09-11 | 2018-02-21 | Institute of Cancer Research: Royal Cancer Hospital (The) | 3-aryl-5-substituted-isoquinolin-1-one compounds and their therapeutic use |
| RU2672885C2 (ru) * | 2013-12-23 | 2018-11-20 | Мерк Патент Гмбх | Производные имидазопиразинона |
| UY36060A (es) | 2014-04-02 | 2015-10-30 | Bayer Pharma AG | Compuestos de azol sustituidos con amida |
| RU2672722C2 (ru) | 2014-04-10 | 2018-11-19 | Хубэй Био-Фармасьютикал Индастриал Текнолоджикал Инститьют Инк. | Аналоги соединений 4н-пиразоло[1,5-а]бензимидазола в качестве ингибиторов parp |
| KR20160007347A (ko) | 2014-07-11 | 2016-01-20 | 에스티팜 주식회사 | 신규한 이미다조트리아지논 또는 이미다조피라지논 유도체, 및 이들의 용도 |
| KR101775356B1 (ko) * | 2015-07-06 | 2017-09-06 | 재단법인 아산사회복지재단 | Parp 및 탄키라제 동시 저해제에 대한 감수성 결정 방법 |
| ES2969565T3 (es) * | 2015-09-30 | 2024-12-13 | Max Planck Ges Zur Foerderung Derwissenschaften E V | Derivados heteroarílicos como inhibidores de la sepiapterina reductasa |
| WO2017055316A1 (en) | 2015-10-01 | 2017-04-06 | Bayer Pharma Aktiengesellschaft | Amido-substituted azole compounds |
| WO2017055313A1 (en) | 2015-10-01 | 2017-04-06 | Bayer Pharma Aktiengesellschaft | Amido-substituted azole compounds |
| SMT202200190T1 (it) | 2015-11-16 | 2022-07-21 | Topadur Pharma Ag | Derivati del 2-fenil-3,4-diidropirrolo[2,1-f] [1,2,4]triazinone come inibitori della fosfodesterasi e loro usi |
| WO2017156350A1 (en) | 2016-03-09 | 2017-09-14 | K-Gen, Inc. | Methods of cancer treatment |
| WO2018078009A1 (en) | 2016-10-29 | 2018-05-03 | Bayer Pharma Aktiengesellschaft | Amido-substituted cyclohexane derivatives |
| WO2018078005A1 (en) | 2016-10-29 | 2018-05-03 | Bayer Pharma Aktiengesellschaft | Amido-substituted azaspiro derivatives as tankyrase inhibitors |
| WO2018087126A1 (en) | 2016-11-09 | 2018-05-17 | Bayer Pharma Aktiengesellschaft | Amido-substituted cyclohexane derivatives as inhibitors of tankyrase |
| CN109180702B (zh) * | 2018-10-29 | 2021-11-30 | 四川大学 | 一种噻吩并嘧啶酮化合物及其用途 |
| CN111961058B (zh) * | 2020-08-03 | 2022-12-16 | 天津全和诚科技有限责任公司 | 4-氨基-吡咯并三嗪衍生物及其制备方法和用途 |
| IL315733A (en) | 2022-04-08 | 2024-11-01 | SHY Therapeutics LLC | Compounds that Interact with RAS Superfamily Proteins for the Treatment of Cancer, Inflammatory, Basoplastic, and Fibrotic Diseases |
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| GB9624482D0 (en) | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
| DE69720965T2 (de) | 1996-02-13 | 2004-02-05 | Astrazeneca Ab | Chinazolinderivate und deren verwendung als vegf hemmer |
| NZ331191A (en) | 1996-03-05 | 2000-03-27 | Zeneca Ltd | 4-anilinoquinazoline derivatives and pharmaceutical compositions thereof |
| GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
| GB9714249D0 (en) | 1997-07-08 | 1997-09-10 | Angiogene Pharm Ltd | Vascular damaging agents |
| GB9900334D0 (en) | 1999-01-07 | 1999-02-24 | Angiogene Pharm Ltd | Tricylic vascular damaging agents |
| GB9900752D0 (en) | 1999-01-15 | 1999-03-03 | Angiogene Pharm Ltd | Benzimidazole vascular damaging agents |
| AU2001258628A1 (en) | 2000-05-31 | 2001-12-11 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
| MXPA02012903A (es) | 2000-07-07 | 2004-07-30 | Angiogene Pharm Ltd | Derivados de colquinol como inhibidores de angiogenesis. |
| MXPA02012905A (es) | 2000-07-07 | 2004-07-30 | Angiogene Pharm Ltd | Derivados de colquinol como agentes de dano vascular.. |
| US7223766B2 (en) * | 2003-03-28 | 2007-05-29 | Scios, Inc. | Bi-cyclic pyrimidine inhibitors of TGFβ |
| KR20070058602A (ko) * | 2004-09-30 | 2007-06-08 | 티보텍 파마슈티칼즈 리미티드 | Ｈｃｖ 저해 바이-사이클릭 피리미딘 |
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| US8299256B2 (en) | 2007-03-08 | 2012-10-30 | Janssen Pharmaceutica Nv | Quinolinone derivatives as PARP and TANK inhibitors |
| EP2134716A1 (en) * | 2007-04-18 | 2009-12-23 | Bristol-Myers Squibb Company | Pyrrolotriazine kinase inhibitors |
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| SI2844659T1 (sl) | 2016-10-28 |
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| RS55062B1 (sr) | 2016-12-30 |
| CN104271580B (zh) | 2017-02-22 |
| KR20150006873A (ko) | 2015-01-19 |
| PL2844659T3 (pl) | 2016-11-30 |
| US9174995B2 (en) | 2015-11-03 |
| WO2013164061A8 (en) | 2014-11-06 |
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| HK1205740A1 (en) | 2015-12-24 |
| ZA201408876B (en) | 2017-06-28 |
| PT2844659T (pt) | 2016-08-31 |
| EP2844659B1 (en) | 2016-05-25 |
| IL235414A (en) | 2017-11-30 |
| WO2013164061A1 (en) | 2013-11-07 |
| CA2872334A1 (en) | 2013-11-07 |
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