JP2011506588A - 抗がん剤としての３−置換−４−オキソ−３，４−ジヒドロ−イミダゾ−［５，１−ｄ］［１，２，３，５］−テトラジン−８−カルボン酸アミド - Google Patents
抗がん剤としての３−置換−４−オキソ−３，４−ジヒドロ−イミダゾ−［５，１−ｄ］［１，２，３，５］−テトラジン−８−カルボン酸アミド Download PDFInfo
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- JP2011506588A JP2011506588A JP2010538886A JP2010538886A JP2011506588A JP 2011506588 A JP2011506588 A JP 2011506588A JP 2010538886 A JP2010538886 A JP 2010538886A JP 2010538886 A JP2010538886 A JP 2010538886A JP 2011506588 A JP2011506588 A JP 2011506588A
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- 125000001931 aliphatic group Chemical group 0.000 claims description 214
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- 125000002947 alkylene group Chemical group 0.000 claims description 121
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 120
- 238000000034 method Methods 0.000 claims description 106
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- 125000000217 alkyl group Chemical group 0.000 claims description 81
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- 125000001425 triazolyl group Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- HGHDIUFFBHTMQV-UHFFFAOYSA-N [4-[2,6-bis(4-aminophenyl)thiopyran-4-ylidene]cyclohexa-2,5-dien-1-ylidene]-dimethylazanium;chloride Chemical compound [Cl-].C1=CC(=[N+](C)C)C=CC1=C1C=C(C=2C=CC(N)=CC=2)SC(C=2C=CC(N)=CC=2)=C1 HGHDIUFFBHTMQV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002785 azepinyl group Chemical group 0.000 claims description 2
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- 239000008280 blood Substances 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 claims description 2
- 125000000532 dioxanyl group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
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- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002632 imidazolidinyl group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 2
- 125000004499 isoxazol-5-yl group Chemical group O1N=CC=C1* 0.000 claims description 2
- 125000002757 morpholinyl group Chemical group 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 2
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 163
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 104
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- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical compound OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 230000008685 targeting Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 229940061353 temodar Drugs 0.000 description 1
- 208000001608 teratocarcinoma Diseases 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- SJMDMGHPMLKLHQ-UHFFFAOYSA-N tert-butyl 2-aminoacetate Chemical compound CC(C)(C)OC(=O)CN SJMDMGHPMLKLHQ-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 201000003120 testicular cancer Diseases 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- 238000011285 therapeutic regimen Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 201000002510 thyroid cancer Diseases 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 208000030901 thyroid gland follicular carcinoma Diseases 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000002723 toxicity assay Methods 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- SEDZOYHHAIAQIW-UHFFFAOYSA-N trimethylsilyl azide Chemical compound C[Si](C)(C)N=[N+]=[N-] SEDZOYHHAIAQIW-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
- 201000005112 urinary bladder cancer Diseases 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
Classifications
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1452007P | 2007-12-18 | 2007-12-18 | |
| PCT/GB2008/004140 WO2009077741A2 (en) | 2007-12-18 | 2008-12-16 | 3-substituted-4-oxo-3,4-dihydro-imidazo-[5,1-d][1,2,3,5-tetrazine-8-carboxylic acid amides and their use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2011506588A true JP2011506588A (ja) | 2011-03-03 |
| JP2011506588A5 JP2011506588A5 (enExample) | 2012-02-09 |
Family
ID=40427129
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010538886A Pending JP2011506588A (ja) | 2007-12-18 | 2008-12-16 | 抗がん剤としての３−置換−４−オキソ−３，４−ジヒドロ−イミダゾ−［５，１−ｄ］［１，２，３，５］−テトラジン−８−カルボン酸アミド |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US8450479B2 (enExample) |
| EP (2) | EP2698370A3 (enExample) |
| JP (1) | JP2011506588A (enExample) |
| CN (1) | CN101945874A (enExample) |
| AR (1) | AR071548A1 (enExample) |
| AU (1) | AU2008337261A1 (enExample) |
| CA (1) | CA2709749A1 (enExample) |
| IL (1) | IL206453A0 (enExample) |
| PE (1) | PE20091101A1 (enExample) |
| TW (1) | TW200934782A (enExample) |
| WO (1) | WO2009077741A2 (enExample) |
| ZA (1) | ZA201004554B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021533164A (ja) * | 2018-08-09 | 2021-12-02 | ザ ボード オブ トラスティーズ オブ ザ ユニバーシテイ オブ イリノイ | イミダゾテトラジン化合物 |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20091101A1 (es) | 2007-12-18 | 2009-07-26 | Pharminox Ltd | AMIDAS DE ACIDO 3-SUBSTITUIDO-4-OXO-3,4-DIHIDRO-IMIDAZO[5,1-d] [1,2,3,5-TETRACINA-8-CARBOXILICO Y SU EMPLEO |
| CA2763766A1 (en) | 2009-06-23 | 2010-12-29 | Pharminox Limited | 3-substituted-8-substituted-3h-imidazo[5,1-d][1,2,3,5-tetrazin-4-one compounds and their use |
| EP2542553A1 (en) * | 2010-03-01 | 2013-01-09 | Pharminox Ltd | Methods and intermediates for the synthesis of 4-oxo-3,4-dihydro-imidazo[5,1-d][1,2,3,5]tetrazines |
| WO2012085501A1 (en) | 2010-12-20 | 2012-06-28 | Pharminox Limited | 8 - sulfo - imidazotetrazin- 4 - one compounds and their use as anticancer drug |
| RU2545458C2 (ru) * | 2013-08-01 | 2015-03-27 | Автономная Некоммерческая Организация "Научно-Исследовательский Центр Биотехнологии Антибиотиков И Других Биологически Активных Веществ "Биоан" | ПРОТИВОТУБЕРКУЛЕЗНОЕ ЛЕКАРСТВЕННОЕ СРЕДСТВО: КОМПОЗИЦИЯ ИМИДАЗО[1,2-b]ТЕТРАЗИНА С ПИРАЗИНАМИДОМ |
| CN108276415B (zh) * | 2018-02-08 | 2019-07-05 | 台州职业技术学院 | 一种烷氧化三唑并四嗪类化合物及其制备方法和应用 |
| US12414952B2 (en) | 2018-11-20 | 2025-09-16 | Merck Sharp & Dohme Llc | Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use |
| JP2022507734A (ja) | 2018-11-20 | 2022-01-18 | メルク・シャープ・アンド・ドーム・コーポレーション | 置換アミノトリアゾロピリミジン及びアミノトリアゾロピラジンアデノシン受容体アンタゴニスト、医薬組成物及びそれらの使用 |
| JP2022511778A (ja) | 2018-11-30 | 2022-02-01 | メルク・シャープ・アンド・ドーム・コーポレーション | アデノシン受容体拮抗薬としての７－、８－及び１０－置換されたアミノトリアゾロキナゾリン誘導体、医薬組成物及びそれらの使用 |
| AR117164A1 (es) | 2018-11-30 | 2021-07-14 | Merck Sharp & Dohme | Derivados de amino-triazoloquinazolina 9-sustituidos como antagonistas del receptor de adenosina, composiciones farmacéuticas y su uso para el tratamiento de diversos tipos de cáncer |
| GB201907813D0 (en) | 2019-05-31 | 2019-07-17 | Univ Nottingham | Therapeutic compounds |
| KR102571751B1 (ko) | 2020-03-24 | 2023-08-25 | 삼성에스디아이 주식회사 | 리튬 이차 전지의 전해질용 첨가제, 리튬 이차 전지용 전해질 및 이를 포함하는 리튬 이차 전지 |
| US20240294478A1 (en) * | 2021-06-18 | 2024-09-05 | Yale University | Anti-cancer compounds and methods of use |
| US20240400572A1 (en) * | 2021-09-23 | 2024-12-05 | Yale University | Compounds and methods for treating cancers that are mgmt deficient regardless of mmr status |
| US20250129083A1 (en) * | 2022-02-01 | 2025-04-24 | The Board Of Trustees Of The University Of Illinois | Imidazotetrazine compounds and treatment of tmz-resistant cancers |
| GEAP202616916A (en) * | 2023-08-04 | 2026-05-25 | Modifi Biosciences Inc | Fluoroalkoxyalkylene-dihydroimidazo[5,1-d]tetrazinone compounds and related compounds and their use in treating medical conditions |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5843975A (ja) * | 1981-08-24 | 1983-03-14 | メイ・アンド・ベイカ−・リミテツド | テトラジン誘導体 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5260291A (en) | 1981-08-24 | 1993-11-09 | Cancer Research Campaign Technology Limited | Tetrazine derivatives |
| GB2125402B (en) | 1982-08-17 | 1985-11-13 | May & Baker Ltd | New tetrazine derivatives |
| US4504475A (en) | 1983-05-24 | 1985-03-12 | Warner Lambert Company | 3-(Haloethyl)-4-oxopyrazolo[5,1-D]-1,2,3,5-tetrazine-8-carboxamide compounds |
| GB9504361D0 (en) | 1995-03-04 | 1995-04-26 | Glaxo Spa | Heterocyclic compounds |
| WO2002057269A1 (en) | 2001-01-18 | 2002-07-25 | Schering Corporation | Synthesis of temozolomide and analogs |
| CN1742723A (zh) | 2004-09-02 | 2006-03-08 | 天津倍方科技发展有限公司 | 含有替莫唑胺－8－羧酸酯的药物组合物以及该类化合物用于制备抗肿瘤药物的用途 |
| PE20091101A1 (es) | 2007-12-18 | 2009-07-26 | Pharminox Ltd | AMIDAS DE ACIDO 3-SUBSTITUIDO-4-OXO-3,4-DIHIDRO-IMIDAZO[5,1-d] [1,2,3,5-TETRACINA-8-CARBOXILICO Y SU EMPLEO |
| GB0807103D0 (en) | 2008-04-18 | 2008-05-21 | Univ Bradford The | Compounds |
| CA2763766A1 (en) | 2009-06-23 | 2010-12-29 | Pharminox Limited | 3-substituted-8-substituted-3h-imidazo[5,1-d][1,2,3,5-tetrazin-4-one compounds and their use |
-
2008
- 2008-12-12 PE PE2008002071A patent/PE20091101A1/es not_active Application Discontinuation
- 2008-12-16 WO PCT/GB2008/004140 patent/WO2009077741A2/en not_active Ceased
- 2008-12-16 EP EP20130175051 patent/EP2698370A3/en not_active Withdrawn
- 2008-12-16 CA CA2709749A patent/CA2709749A1/en not_active Abandoned
- 2008-12-16 JP JP2010538886A patent/JP2011506588A/ja active Pending
- 2008-12-16 CN CN2008801269450A patent/CN101945874A/zh active Pending
- 2008-12-16 AU AU2008337261A patent/AU2008337261A1/en not_active Abandoned
- 2008-12-16 US US12/808,604 patent/US8450479B2/en not_active Expired - Fee Related
- 2008-12-16 EP EP08861839A patent/EP2229393A2/en not_active Withdrawn
- 2008-12-18 AR ARP080105534A patent/AR071548A1/es unknown
- 2008-12-18 TW TW097149411A patent/TW200934782A/zh unknown
-
2010
- 2010-06-17 IL IL206453A patent/IL206453A0/en unknown
- 2010-06-28 ZA ZA2010/04554A patent/ZA201004554B/en unknown
-
2013
- 2013-05-24 US US13/901,680 patent/US20130338104A1/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5843975A (ja) * | 1981-08-24 | 1983-03-14 | メイ・アンド・ベイカ−・リミテツド | テトラジン誘導体 |
Non-Patent Citations (2)
| Title |
|---|
| JPN5011002345; ＡＲＲＯＷＳＭＩＴＨ Ｊ: 'ＡＮＴＩＴＵＭＯＵＲ ＩＭＩＤＡＺＯＴＥＴＲＡＺＩＮＥＳ． ＰＡＲＴ ３９．１ ＳＹＮＴＨＥＳＩＳ ＯＦ ＢＩＳ （ＩＭＩＤＡＺＯＴＥＴＲＡＺＩＮＥ）Ｓ 以下備考' ＪＯＵＲＮＡＬ ＯＦ ＴＨＥ ＣＨＥＭＩＣＡＬ ＳＯＣＩＥＴＹ． ＰＥＲＫＩＮ ＴＲＡＮＳＡＣＴＩＯＮＳ １ Ｖ２４, 20000101, Ｐ４４３２-４４３８, ＣＨＥＭＩＣＡＬ ＳＯＣＩＥＴＹ * |
| JPN6013050300; 'Ａ Ｎｅｗ Ｓｙｎｔｈｅｔｉｃ Ｍｅｔｈｏｄ ｆｏｒ ｔｈｅ ２-Ｓｕｂｓｔｉｔｕｔｉｏｎ ｏｆ Ｎ' Ｊ．Ｏｒｇ．Ｃｈｅｍ． ５４, 1989, ２９４９-２９５２ * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2021533164A (ja) * | 2018-08-09 | 2021-12-02 | ザ ボード オブ トラスティーズ オブ ザ ユニバーシテイ オブ イリノイ | イミダゾテトラジン化合物 |
| JP7487949B2 (ja) | 2018-08-09 | 2024-05-21 | ザ ボード オブ トラスティーズ オブ ザ ユニバーシテイ オブ イリノイ | イミダゾテトラジン化合物 |
| US12234240B2 (en) | 2018-08-09 | 2025-02-25 | The Board Of Trustees Of The University Of Illinois | Substituted imidazo[5,1-d][1,2,3,5]tetrazines for the treatment of cancer |
Also Published As
| Publication number | Publication date |
|---|---|
| US20130338104A1 (en) | 2013-12-19 |
| US20100286088A1 (en) | 2010-11-11 |
| TW200934782A (en) | 2009-08-16 |
| IL206453A0 (en) | 2010-12-30 |
| EP2698370A3 (en) | 2014-07-16 |
| CN101945874A (zh) | 2011-01-12 |
| ZA201004554B (en) | 2011-09-28 |
| US8450479B2 (en) | 2013-05-28 |
| WO2009077741A3 (en) | 2009-12-03 |
| EP2698370A2 (en) | 2014-02-19 |
| EP2229393A2 (en) | 2010-09-22 |
| AU2008337261A1 (en) | 2009-06-25 |
| PE20091101A1 (es) | 2009-07-26 |
| CA2709749A1 (en) | 2009-06-25 |
| WO2009077741A2 (en) | 2009-06-25 |
| AR071548A1 (es) | 2010-06-30 |
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