IL234713A - The history of ovarian pyrazinone in the preparation, preparation and pharmaceutical preparations containing them - Google Patents
The history of ovarian pyrazinone in the preparation, preparation and pharmaceutical preparations containing themInfo
- Publication number
- IL234713A IL234713A IL234713A IL23471314A IL234713A IL 234713 A IL234713 A IL 234713A IL 234713 A IL234713 A IL 234713A IL 23471314 A IL23471314 A IL 23471314A IL 234713 A IL234713 A IL 234713A
- Authority
- IL
- Israel
- Prior art keywords
- denotes
- phenyl
- unsubstituted
- mmol
- mono
- Prior art date
Links
- -1 Bicyclic pyrazinone derivatives Chemical class 0.000 title claims description 250
- 238000002360 preparation method Methods 0.000 title claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 title description 17
- 150000001875 compounds Chemical class 0.000 claims description 160
- 239000000203 mixture Substances 0.000 claims description 74
- 150000003839 salts Chemical class 0.000 claims description 68
- 101100372601 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) POR2 gene Proteins 0.000 claims description 31
- 101100099673 Zea mays TIP2-3 gene Proteins 0.000 claims description 31
- 125000002757 morpholinyl group Chemical group 0.000 claims description 28
- 125000003386 piperidinyl group Chemical group 0.000 claims description 28
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 28
- 239000012453 solvate Substances 0.000 claims description 28
- 229910052801 chlorine Inorganic materials 0.000 claims description 27
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
- 101100406879 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) par-2 gene Proteins 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 22
- 238000011282 treatment Methods 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 125000002393 azetidinyl group Chemical group 0.000 claims description 19
- 125000004193 piperazinyl group Chemical group 0.000 claims description 19
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 16
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 15
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 15
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 15
- 125000002971 oxazolyl group Chemical group 0.000 claims description 15
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 13
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 12
- 108010081348 HRT1 protein Hairy Proteins 0.000 claims description 12
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims description 12
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 12
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 12
- 125000002541 furyl group Chemical group 0.000 claims description 12
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 12
- 125000002883 imidazolyl group Chemical group 0.000 claims description 12
- 125000005945 imidazopyridyl group Chemical group 0.000 claims description 12
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 12
- 125000001041 indolyl group Chemical group 0.000 claims description 12
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 12
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 12
- 125000005493 quinolyl group Chemical group 0.000 claims description 12
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 12
- 125000000335 thiazolyl group Chemical group 0.000 claims description 12
- 125000001544 thienyl group Chemical group 0.000 claims description 12
- 125000001425 triazolyl group Chemical group 0.000 claims description 12
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 7
- 125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 claims description 7
- 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- 125000003566 oxetanyl group Chemical group 0.000 claims description 7
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims description 7
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 6
- PBGKNXWGYQPUJK-UHFFFAOYSA-N 4-chloro-2-nitroaniline Chemical compound NC1=CC=C(Cl)C=C1[N+]([O-])=O PBGKNXWGYQPUJK-UHFFFAOYSA-N 0.000 claims description 6
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 claims description 6
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 6
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 6
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 6
- 229910052727 yttrium Inorganic materials 0.000 claims description 6
- 238000006069 Suzuki reaction reaction Methods 0.000 claims description 4
- 125000003158 alcohol group Chemical group 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 144
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- 238000004128 high performance liquid chromatography Methods 0.000 description 85
- 239000000243 solution Substances 0.000 description 79
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
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- 239000011541 reaction mixture Substances 0.000 description 73
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 60
- 238000005160 1H NMR spectroscopy Methods 0.000 description 55
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 55
- 235000002639 sodium chloride Nutrition 0.000 description 51
- 235000019439 ethyl acetate Nutrition 0.000 description 44
- 229940093499 ethyl acetate Drugs 0.000 description 43
- 239000000725 suspension Substances 0.000 description 42
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 40
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
- 239000007787 solid Substances 0.000 description 38
- 230000015572 biosynthetic process Effects 0.000 description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 34
- 239000004480 active ingredient Substances 0.000 description 33
- 238000003786 synthesis reaction Methods 0.000 description 33
- 239000003480 eluent Substances 0.000 description 32
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
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- 102100037664 Poly [ADP-ribose] polymerase tankyrase-1 Human genes 0.000 description 27
- 108010017601 Tankyrases Proteins 0.000 description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 25
- 239000012074 organic phase Substances 0.000 description 25
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 24
- 229910052938 sodium sulfate Inorganic materials 0.000 description 24
- 235000011152 sodium sulphate Nutrition 0.000 description 24
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 23
- 230000000694 effects Effects 0.000 description 23
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- 239000003112 inhibitor Substances 0.000 description 11
- 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 10
- 101000663006 Homo sapiens Poly [ADP-ribose] polymerase tankyrase-1 Proteins 0.000 description 10
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- WSZIQFBLHPZUBT-UHFFFAOYSA-N 3-(4-bromophenyl)-2h-pyrrolo[1,2-a]pyrazin-1-one Chemical compound C1=CC(Br)=CC=C1C(NC1=O)=CN2C1=CC=C2 WSZIQFBLHPZUBT-UHFFFAOYSA-N 0.000 description 7
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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
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- 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
- A61K31/4985—Pyrazines or piperazines ortho- or peri-condensed with heterocyclic ring 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
- A61K31/495—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
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/506—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim 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
- A61P25/00—Drugs for disorders of the nervous system
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- 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
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- 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)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
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- Veterinary Medicine (AREA)
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- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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- Diabetes (AREA)
- Cardiology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12002215 | 2012-03-28 | ||
| PCT/EP2013/000827 WO2013143663A1 (en) | 2012-03-28 | 2013-03-19 | Bicyclic pyrazinone derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL234713A true IL234713A (en) | 2016-09-29 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL234713A IL234713A (en) | 2012-03-28 | 2014-09-18 | The history of ovarian pyrazinone in the preparation, preparation and pharmaceutical preparations containing them |
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| Country | Link |
|---|---|
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| EP (1) | EP2831077B1 (enExample) |
| JP (1) | JP6096879B2 (enExample) |
| KR (1) | KR102070567B1 (enExample) |
| CN (1) | CN104169284B (enExample) |
| AR (1) | AR090496A1 (enExample) |
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| CA (1) | CA2868620C (enExample) |
| CL (1) | CL2014002557A1 (enExample) |
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| EA (1) | EA027416B1 (enExample) |
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| ES (1) | ES2585044T3 (enExample) |
| HR (1) | HRP20160908T1 (enExample) |
| HU (1) | HUE030067T2 (enExample) |
| IL (1) | IL234713A (enExample) |
| MX (1) | MX351149B (enExample) |
| MY (1) | MY172308A (enExample) |
| NZ (1) | NZ630489A (enExample) |
| PE (1) | PE20142186A1 (enExample) |
| PH (1) | PH12014501829A1 (enExample) |
| PL (1) | PL2831077T3 (enExample) |
| PT (1) | PT2831077T (enExample) |
| RS (1) | RS54997B1 (enExample) |
| SG (1) | SG11201405750YA (enExample) |
| SI (1) | SI2831077T1 (enExample) |
| TW (1) | TWI576346B (enExample) |
| UA (1) | UA112795C2 (enExample) |
| WO (1) | WO2013143663A1 (enExample) |
| ZA (1) | ZA201407828B (enExample) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2822656T3 (en) | 2012-03-07 | 2017-01-30 | Inst Of Cancer Research: Royal Cancer Hospital (The) | 3-aryl-5-substituted-isoquinolin-1-one compounds and their therapeutic use |
| HUE030067T2 (en) | 2012-03-28 | 2017-04-28 | Merck Patent Gmbh | Bicyclic pyrazinone derivatives |
| KR20150011838A (ko) * | 2012-06-20 | 2015-02-02 | 에프. 호프만-라 로슈 아게 | 탄키라아제 억제제로서의 피롤로피라존 |
| CN105722835B (zh) | 2013-09-11 | 2018-07-31 | 癌症研究协会:皇家癌症医院 | 3-芳基-5-取代的-异喹啉-1-酮化合物及它们的疗法应用 |
| MX364859B (es) | 2013-12-23 | 2019-05-09 | Merck Patent Gmbh | Derivados de imidazopirazinona. |
| KR20160007347A (ko) | 2014-07-11 | 2016-01-20 | 에스티팜 주식회사 | 신규한 이미다조트리아지논 또는 이미다조피라지논 유도체, 및 이들의 용도 |
| WO2016006974A2 (en) * | 2014-07-11 | 2016-01-14 | St Pharm Co., Ltd. | Novel triazolopyrimidinone or triazolopyridinone derivatives, and use thereof |
| WO2016006975A2 (en) * | 2014-07-11 | 2016-01-14 | St Pharm Co., Ltd. | Novel imidazotriazinone or imidazopyrazinone derivatives, and use thereof |
| KR101739003B1 (ko) * | 2014-07-11 | 2017-05-23 | 에스티팜 주식회사 | 신규한 트리아졸로피리미디논 또는 트리아졸로피리디논 유도체, 및 이들의 용도 |
| KR20170090476A (ko) * | 2014-12-05 | 2017-08-07 | 어레이 바이오파마 인크. | 야누스 키나제 저해제로서의 4,6-치환된-피라졸로[1,5-a]피라진 |
| HK1255269A1 (zh) | 2015-08-17 | 2019-08-09 | Lupin Limited | 作为parp抑制剂的杂芳基衍生物 |
| RS60261B1 (sr) | 2016-02-24 | 2020-06-30 | Pfizer | Pirazolo[1,5-a]pirazin-4-il derivativi kao jak-inhibitori |
| WO2017156350A1 (en) | 2016-03-09 | 2017-09-14 | K-Gen, Inc. | Methods of cancer treatment |
| US11254668B2 (en) | 2017-08-14 | 2022-02-22 | Pfizer Inc. | Pyrazolo[1,5-A]pyrazin-4-yl and related derivatives |
| MX2020012201A (es) * | 2018-05-17 | 2021-01-29 | Bayer Ag | Derivados sustituidos de la carboxamida dihidropirazolo pirazina. |
| GB2632307A (en) * | 2023-08-02 | 2025-02-05 | Duke Street Bio Ltd | PARP1 inhibitor compounds |
| GB2632441A (en) * | 2023-08-08 | 2025-02-12 | Duke Street Bio Ltd | Deuterated PARP1 inhibitor compounds |
| WO2025084446A1 (ko) * | 2023-10-16 | 2025-04-24 | 에스티팜 주식회사 | 트리아졸로피리미디논 유도체의 결정형 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB9624482D0 (en) | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
| BR9707495A (pt) | 1996-02-13 | 1999-07-27 | Zeneca Ltd | Derivado de quinazolina processo para a preparação do mesmo composição farmacêutica e processo para a produç o de um efeito antiangiogênico e/ou de redução de permeabilidade vascular em um animal de sangue quente |
| JP4464466B2 (ja) | 1996-03-05 | 2010-05-19 | アストラゼネカ・ユーケイ・リミテッド | ４―アニリノキナゾリン誘導体 |
| GB9718972D0 (en) | 1996-09-25 | 1997-11-12 | Zeneca Ltd | Chemical compounds |
| SE9702706D0 (sv) | 1997-07-11 | 1997-07-11 | Pharmacia & Upjohn Ab | Prostaglandin derivatives devoid of side-effects for the treatment of glaucoma |
| 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 |
| IL152682A0 (en) | 2000-05-31 | 2003-06-24 | Astrazeneca Ab | Indole derivatives with vascular damaging activity |
| JP2004502766A (ja) | 2000-07-07 | 2004-01-29 | アンギオジェン・ファーマシューティカルズ・リミテッド | 血管損傷剤としてのコルヒノール誘導体 |
| CA2410562A1 (en) | 2000-07-07 | 2002-01-31 | Angiogene Pharmaceuticals Limited | Colchinol derivatives as angiogenesis inhibitors |
| EP2032140A1 (en) * | 2006-05-31 | 2009-03-11 | Istituto di Richerche di Biologia Molecolare P. Angeletti S.p.A. | Pyrrolo[1,2-a]pyrazin-1(2h)-one and pyrrolo[1,2-d][1,2,4]triazin-1(2h)-one derivatives as inhibitors of poly(adp-ribose)polymerase(parp) |
| CN101616919B (zh) * | 2006-12-28 | 2012-10-10 | 雅培制药有限公司 | 聚（adp核糖）聚合酶抑制剂 |
| ATE542799T1 (de) | 2007-03-08 | 2012-02-15 | Janssen Pharmaceutica Nv | Chinolinonderivate als parp und tank-inhibitoren |
| DE102007032349A1 (de) * | 2007-07-11 | 2009-01-15 | Bayer Healthcare Ag | Imidazo-, Pyrazolopyrazine und Imidazotriazine und ihre Verwendung |
| WO2009130232A1 (en) * | 2008-04-24 | 2009-10-29 | Glaxo Group Limited | Pyrazolo [1, 5 -a] pyrazine derivatives as antagonists of v1b receptors |
| WO2009130231A1 (en) | 2008-04-24 | 2009-10-29 | Glaxo Group Limited | Pyrrolo [1, 2-a] pyrazine derivatives as vasopressin vib receptor antagonists |
| EP2350084B1 (en) | 2008-10-17 | 2015-06-24 | Boehringer Ingelheim International GmbH | Tetra-aza-heterocycles as phosphatidylinositol-3-kinases (pi3-kinases) inhibitor |
| CA2787714C (en) | 2010-01-22 | 2019-04-09 | Joaquin Pastor Fernandez | Inhibitors of pi3 kinase |
| CA2794861A1 (en) * | 2010-04-16 | 2011-10-20 | Abbvie Inc. | Pyrrolopyrazinone inhibitors of kinases |
| CN102229611B (zh) * | 2011-04-26 | 2012-12-12 | 山东大学 | 2,6-二芳基吡唑并[1,5-a]吡嗪-4(5H)-酮化合物及其应用 |
| HUE030067T2 (en) | 2012-03-28 | 2017-04-28 | Merck Patent Gmbh | Bicyclic pyrazinone derivatives |
| KR20150011838A (ko) * | 2012-06-20 | 2015-02-02 | 에프. 호프만-라 로슈 아게 | 탄키라아제 억제제로서의 피롤로피라존 |
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2013
- 2013-03-19 HU HUE13712685A patent/HUE030067T2/en unknown
- 2013-03-19 RS RS20160596A patent/RS54997B1/sr unknown
- 2013-03-19 AU AU2013242492A patent/AU2013242492B2/en active Active
- 2013-03-19 PL PL13712685.0T patent/PL2831077T3/pl unknown
- 2013-03-19 UA UAA201411566A patent/UA112795C2/uk unknown
- 2013-03-19 MX MX2014011420A patent/MX351149B/es active IP Right Grant
- 2013-03-19 WO PCT/EP2013/000827 patent/WO2013143663A1/en not_active Ceased
- 2013-03-19 ES ES13712685.0T patent/ES2585044T3/es active Active
- 2013-03-19 HR HRP20160908TT patent/HRP20160908T1/hr unknown
- 2013-03-19 PE PE2014001502A patent/PE20142186A1/es active IP Right Grant
- 2013-03-19 DK DK13712685.0T patent/DK2831077T3/en active
- 2013-03-19 NZ NZ630489A patent/NZ630489A/en not_active IP Right Cessation
- 2013-03-19 PT PT137126850T patent/PT2831077T/pt unknown
- 2013-03-19 JP JP2015502129A patent/JP6096879B2/ja active Active
- 2013-03-19 SG SG11201405750YA patent/SG11201405750YA/en unknown
- 2013-03-19 EP EP13712685.0A patent/EP2831077B1/en active Active
- 2013-03-19 CN CN201380017205.4A patent/CN104169284B/zh active Active
- 2013-03-19 US US14/388,270 patent/US9120805B2/en active Active
- 2013-03-19 CA CA2868620A patent/CA2868620C/en active Active
- 2013-03-19 EA EA201401062A patent/EA027416B1/ru not_active IP Right Cessation
- 2013-03-19 KR KR1020147029895A patent/KR102070567B1/ko not_active Expired - Fee Related
- 2013-03-19 SI SI201330254A patent/SI2831077T1/sl unknown
- 2013-03-19 MY MYPI2014702730A patent/MY172308A/en unknown
- 2013-03-26 AR ARP130100972A patent/AR090496A1/es active IP Right Grant
- 2013-03-27 TW TW102110996A patent/TWI576346B/zh active
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- 2014-08-13 PH PH12014501829A patent/PH12014501829A1/en unknown
- 2014-08-20 CO CO14182299A patent/CO7111292A2/es unknown
- 2014-09-18 IL IL234713A patent/IL234713A/en active IP Right Grant
- 2014-09-25 CL CL2014002557A patent/CL2014002557A1/es unknown
- 2014-10-27 EC ECIEPI201424526A patent/ECSP14024526A/es unknown
- 2014-10-27 ZA ZA2014/07828A patent/ZA201407828B/en unknown
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| KB | Patent renewed | ||
| KB | Patent renewed |