JP6097820B2 - ピロロトリアジノン誘導体 - Google Patents
ピロロトリアジノン誘導体 Download PDFInfo
- Publication number
- JP6097820B2 JP6097820B2 JP2015509321A JP2015509321A JP6097820B2 JP 6097820 B2 JP6097820 B2 JP 6097820B2 JP 2015509321 A JP2015509321 A JP 2015509321A JP 2015509321 A JP2015509321 A JP 2015509321A JP 6097820 B2 JP6097820 B2 JP 6097820B2
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- Prior art keywords
- het
- pharmaceutically acceptable
- phenyl
- mixture
- compounds
- 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 5-chloro-2-fluorophenyl Chemical group 0.000 claims description 148
- 150000001875 compounds Chemical class 0.000 claims description 144
- 150000003839 salts Chemical class 0.000 claims description 71
- 239000000203 mixture Substances 0.000 claims description 69
- 239000004480 active ingredient Substances 0.000 claims description 36
- 239000012453 solvate Substances 0.000 claims description 31
- 206010028980 Neoplasm Diseases 0.000 claims description 25
- 238000011282 treatment Methods 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 201000011510 cancer Diseases 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 17
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000002585 base Substances 0.000 claims description 15
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 14
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 8
- 125000004185 ester group Chemical group 0.000 claims description 8
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 7
- 206010061218 Inflammation Diseases 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 210000003169 central nervous system Anatomy 0.000 claims description 7
- 230000004054 inflammatory process Effects 0.000 claims description 7
- 201000006417 multiple sclerosis Diseases 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 208000001738 Nervous System Trauma Diseases 0.000 claims description 6
- 210000004369 blood Anatomy 0.000 claims description 6
- 239000008280 blood Substances 0.000 claims description 6
- 208000028412 nervous system injury Diseases 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 5
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 4
- 125000003158 alcohol group Chemical group 0.000 claims description 4
- 210000001508 eye Anatomy 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 229910052740 iodine Inorganic materials 0.000 claims description 4
- 210000000214 mouth Anatomy 0.000 claims description 4
- 210000003800 pharynx Anatomy 0.000 claims description 4
- 239000003981 vehicle Substances 0.000 claims description 4
- 210000004556 brain Anatomy 0.000 claims description 3
- 210000000481 breast Anatomy 0.000 claims description 3
- 210000003734 kidney Anatomy 0.000 claims description 3
- 210000004185 liver Anatomy 0.000 claims description 3
- 210000004072 lung Anatomy 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- 210000000496 pancreas Anatomy 0.000 claims description 3
- 210000003491 skin Anatomy 0.000 claims description 3
- 210000000988 bone and bone Anatomy 0.000 claims description 2
- 210000000621 bronchi Anatomy 0.000 claims description 2
- 201000007455 central nervous system cancer Diseases 0.000 claims description 2
- 210000003679 cervix uteri Anatomy 0.000 claims description 2
- 210000001072 colon Anatomy 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 210000003238 esophagus Anatomy 0.000 claims description 2
- 210000004392 genitalia Anatomy 0.000 claims description 2
- 210000003128 head Anatomy 0.000 claims description 2
- 210000000867 larynx Anatomy 0.000 claims description 2
- 210000001165 lymph node Anatomy 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 210000003739 neck Anatomy 0.000 claims description 2
- 210000001672 ovary Anatomy 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 210000002307 prostate Anatomy 0.000 claims description 2
- 210000000664 rectum Anatomy 0.000 claims description 2
- 210000002784 stomach Anatomy 0.000 claims description 2
- 210000001550 testis Anatomy 0.000 claims description 2
- 210000001685 thyroid gland Anatomy 0.000 claims description 2
- 210000003932 urinary bladder Anatomy 0.000 claims description 2
- 210000004291 uterus Anatomy 0.000 claims description 2
- 241000023320 Luma <angiosperm> Species 0.000 claims 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims 2
- 210000000038 chest Anatomy 0.000 claims 1
- 230000006806 disease prevention Effects 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- 239000000243 solution Substances 0.000 description 53
- 235000002639 sodium chloride Nutrition 0.000 description 52
- 238000004949 mass spectrometry Methods 0.000 description 44
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 41
- 238000004128 high performance liquid chromatography Methods 0.000 description 40
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- 102100037664 Poly [ADP-ribose] polymerase tankyrase-1 Human genes 0.000 description 35
- 239000011541 reaction mixture Substances 0.000 description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 29
- 108010017601 Tankyrases Proteins 0.000 description 28
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- 239000007787 solid Substances 0.000 description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- 230000000694 effects Effects 0.000 description 23
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
- 238000006243 chemical reaction Methods 0.000 description 22
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- 239000000725 suspension Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 19
- 239000003480 eluent Substances 0.000 description 19
- 239000000843 powder Substances 0.000 description 19
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
- 238000003556 assay Methods 0.000 description 16
- 210000004027 cell Anatomy 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000012074 organic phase Substances 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 14
- 235000019439 ethyl acetate Nutrition 0.000 description 14
- 239000003112 inhibitor Substances 0.000 description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
- 239000008194 pharmaceutical composition Substances 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 13
- 238000009472 formulation Methods 0.000 description 13
- 125000003386 piperidinyl group Chemical group 0.000 description 13
- 239000003826 tablet Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229910052938 sodium sulfate Inorganic materials 0.000 description 12
- 235000011152 sodium sulphate Nutrition 0.000 description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 10
- 101000663006 Homo sapiens Poly [ADP-ribose] polymerase tankyrase-1 Proteins 0.000 description 10
- 238000013459 approach Methods 0.000 description 10
- VYLVYHXQOHJDJL-UHFFFAOYSA-K cerium trichloride Chemical compound Cl[Ce](Cl)Cl VYLVYHXQOHJDJL-UHFFFAOYSA-K 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- 230000005764 inhibitory process Effects 0.000 description 10
- 229960005419 nitrogen Drugs 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000000758 substrate Substances 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- 102100035683 Axin-2 Human genes 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
- 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 description 8
- 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 description 8
- 208000035475 disorder Diseases 0.000 description 8
- 238000002868 homogeneous time resolved fluorescence Methods 0.000 description 8
- 238000001727 in vivo Methods 0.000 description 8
- 239000011777 magnesium Substances 0.000 description 8
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
- 101150096411 AXIN2 gene Proteins 0.000 description 7
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- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 7
- 101001113483 Homo sapiens Poly [ADP-ribose] polymerase 1 Proteins 0.000 description 7
- 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 description 7
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 229910002091 carbon monoxide Inorganic materials 0.000 description 7
- 230000000875 corresponding effect Effects 0.000 description 7
- 235000019253 formic acid Nutrition 0.000 description 7
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- 125000002757 morpholinyl group Chemical group 0.000 description 7
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- 150000003254 radicals Chemical class 0.000 description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 7
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 7
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 6
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
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- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 4
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- NXQGGXCHGDYOHB-UHFFFAOYSA-L cyclopenta-1,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+) Chemical compound [Fe+2].Cl[Pd]Cl.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1.[CH-]1C=CC(P(C=2C=CC=CC=2)C=2C=CC=CC=2)=C1 NXQGGXCHGDYOHB-UHFFFAOYSA-L 0.000 description 4
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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
-
- 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
-
- 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 |
|---|---|---|---|
| EP12003445.9 | 2012-05-04 | ||
| EP12003445 | 2012-05-04 | ||
| PCT/EP2013/001026 WO2013164061A1 (en) | 2012-05-04 | 2013-04-06 | Pyrrolotriazinone derivatives |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015515961A JP2015515961A (ja) | 2015-06-04 |
| JP2015515961A5 JP2015515961A5 (https=) | 2016-06-02 |
| JP6097820B2 true JP6097820B2 (ja) | 2017-03-15 |
Family
ID=48050660
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015509321A Expired - Fee Related JP6097820B2 (ja) | 2012-05-04 | 2013-04-06 | ピロロトリアジノン誘導体 |
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=) |
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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 |
| WO2008092861A1 (en) * | 2007-01-30 | 2008-08-07 | Janssen Pharmaceutica N.V. | Bicyclic derivatives as ep4 agonists |
| 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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| EP2844659A1 (en) | 2015-03-11 |
| SI2844659T1 (sl) | 2016-10-28 |
| HRP20161033T1 (hr) | 2016-10-21 |
| SG11201406997WA (en) | 2014-11-27 |
| HUE028325T2 (en) | 2016-12-28 |
| AR090896A1 (es) | 2014-12-17 |
| EA027628B1 (ru) | 2017-08-31 |
| MX2014013090A (es) | 2014-12-08 |
| EA201401212A1 (ru) | 2015-08-31 |
| ES2587939T3 (es) | 2016-10-27 |
| JP2015515961A (ja) | 2015-06-04 |
| CA2872334C (en) | 2020-06-30 |
| AU2013257018B2 (en) | 2017-02-16 |
| AU2013257018A1 (en) | 2014-12-18 |
| MX357502B (es) | 2018-07-12 |
| 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 |
| US20150133453A1 (en) | 2015-05-14 |
| CN104271580A (zh) | 2015-01-07 |
| 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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