CA2651979A1 - Derives de la triazolopyridazine - Google Patents
Derives de la triazolopyridazine Download PDFInfo
- Publication number
- CA2651979A1 CA2651979A1 CA002651979A CA2651979A CA2651979A1 CA 2651979 A1 CA2651979 A1 CA 2651979A1 CA 002651979 A CA002651979 A CA 002651979A CA 2651979 A CA2651979 A CA 2651979A CA 2651979 A1 CA2651979 A1 CA 2651979A1
- Authority
- CA
- Canada
- Prior art keywords
- membered
- triazolo
- pyridazin
- compound
- aryl
- 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.)
- Abandoned
Links
- CBHTTYDJRXOHHL-UHFFFAOYSA-N 2h-triazolo[4,5-c]pyridazine Chemical class N1=NC=CC2=C1N=NN2 CBHTTYDJRXOHHL-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 168
- 150000003839 salts Chemical class 0.000 claims abstract description 42
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
- 241000124008 Mammalia Species 0.000 claims abstract description 16
- -1 -C(O)CH3 Chemical group 0.000 claims description 53
- 206010028980 Neoplasm Diseases 0.000 claims description 45
- 125000001072 heteroaryl group Chemical group 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 238000011282 treatment Methods 0.000 claims description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 27
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 25
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 21
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 20
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 17
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 208000035475 disorder Diseases 0.000 claims description 17
- 201000011510 cancer Diseases 0.000 claims description 16
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 14
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 8
- 208000014829 head and neck neoplasm Diseases 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 206010006187 Breast cancer Diseases 0.000 claims description 7
- 208000026310 Breast neoplasm Diseases 0.000 claims description 7
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims description 7
- 208000005718 Stomach Neoplasms Diseases 0.000 claims description 7
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000004043 oxo group Chemical group O=* 0.000 claims description 7
- 201000002528 pancreatic cancer Diseases 0.000 claims description 7
- 208000008443 pancreatic carcinoma Diseases 0.000 claims description 7
- 208000032612 Glial tumor Diseases 0.000 claims description 6
- 206010018338 Glioma Diseases 0.000 claims description 6
- 206010039491 Sarcoma Diseases 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
- 208000032839 leukemia Diseases 0.000 claims description 6
- 208000008839 Kidney Neoplasms Diseases 0.000 claims description 5
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- 206010017758 gastric cancer Diseases 0.000 claims description 5
- 208000020816 lung neoplasm Diseases 0.000 claims description 5
- 201000011549 stomach cancer Diseases 0.000 claims description 5
- WKCHRDXPLNKEOL-UHFFFAOYSA-N 7-methyl-6-[[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl]quinoline Chemical compound CC1=CC2=NC=CC=C2C=C1CC(N1N=2)=NN=C1C=CC=2C=1C=NN(C)C=1 WKCHRDXPLNKEOL-UHFFFAOYSA-N 0.000 claims description 4
- 206010009944 Colon cancer Diseases 0.000 claims description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims description 4
- 206010038389 Renal cancer Diseases 0.000 claims description 4
- 201000010982 kidney cancer Diseases 0.000 claims description 4
- 201000007270 liver cancer Diseases 0.000 claims description 4
- 208000014018 liver neoplasm Diseases 0.000 claims description 4
- 201000005202 lung cancer Diseases 0.000 claims description 4
- 201000001441 melanoma Diseases 0.000 claims description 4
- 201000000050 myeloid neoplasm Diseases 0.000 claims description 4
- XTCOLZQEGQSACV-UHFFFAOYSA-N 4-[3-(quinolin-6-ylmethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=NN2C(CC=3C=C4C=CC=NC4=CC=3)=NN=C2C=C1 XTCOLZQEGQSACV-UHFFFAOYSA-N 0.000 claims description 3
- ZKFWMJOPGZGDIU-UHFFFAOYSA-N 6-[[6-(1H-pyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]methyl]quinoline Chemical compound C=1C=C2N=CC=CC2=CC=1CC(N1N=2)=NN=C1C=CC=2C=1C=NNC=1 ZKFWMJOPGZGDIU-UHFFFAOYSA-N 0.000 claims description 3
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- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 3
- 208000026037 malignant tumor of neck Diseases 0.000 claims description 3
- PQHYFVORICIMQW-UHFFFAOYSA-N 2-[[3-(1-quinolin-6-ylethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]amino]ethanol Chemical compound N1=CC=CC2=CC(C(C=3N4N=C(NCCO)C=CC4=NN=3)C)=CC=C21 PQHYFVORICIMQW-UHFFFAOYSA-N 0.000 claims description 2
- GFFOZPOIVRIOFY-UHFFFAOYSA-N 3-[(7-methylquinolin-6-yl)methyl]-n-(oxolan-3-yl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine Chemical compound CC1=CC2=NC=CC=C2C=C1CC(N1N=2)=NN=C1C=CC=2NC1CCOC1 GFFOZPOIVRIOFY-UHFFFAOYSA-N 0.000 claims description 2
- ZZPRSODDIBGQOO-ZDUSSCGKSA-N 4-[3-[(1s)-1-(1h-pyrrolo[2,3-b]pyridin-3-yl)ethyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]benzonitrile Chemical compound N=1N2C([C@H](C=3C4=CC=CN=C4NC=3)C)=NN=C2C=CC=1C1=CC=C(C#N)C=C1 ZZPRSODDIBGQOO-ZDUSSCGKSA-N 0.000 claims description 2
- RPZJELRWJSCLHY-HNNXBMFYSA-N 4-[3-[(1s)-1-quinolin-6-ylethyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-yl]benzonitrile Chemical compound N=1N2C([C@@H](C)C=3C=C4C=CC=NC4=CC=3)=NN=C2C=CC=1C1=CC=C(C#N)C=C1 RPZJELRWJSCLHY-HNNXBMFYSA-N 0.000 claims description 2
- NDEVWCAZDRRLOZ-NSHDSACASA-N 6-(1-methylpyrazol-4-yl)-3-[(1s)-1-(1h-pyrrolo[2,3-b]pyridin-3-yl)ethyl]-[1,2,4]triazolo[4,3-b]pyridazine Chemical compound N=1N2C([C@H](C=3C4=CC=CN=C4NC=3)C)=NN=C2C=CC=1C=1C=NN(C)C=1 NDEVWCAZDRRLOZ-NSHDSACASA-N 0.000 claims description 2
- VQYHPUHKYSSEOB-ZDUSSCGKSA-N 6-[(1s)-1-[6-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl]ethyl]quinoline Chemical compound N=1N2C([C@@H](C)C=3C=C4C=CC=NC4=CC=3)=NN=C2C=CC=1C=1C=NN(C)C=1 VQYHPUHKYSSEOB-ZDUSSCGKSA-N 0.000 claims description 2
- ZGUCLZCHJHIWBW-UHFFFAOYSA-N n-cyclopentyl-3-[(7-methylquinolin-6-yl)methyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-amine Chemical compound CC1=CC2=NC=CC=C2C=C1CC(N1N=2)=NN=C1C=CC=2NC1CCCC1 ZGUCLZCHJHIWBW-UHFFFAOYSA-N 0.000 claims description 2
- LLYNUJHWODYAPQ-ZDUSSCGKSA-N n-propan-2-yl-3-[(1s)-1-quinolin-6-ylethyl]-[1,2,4]triazolo[4,3-b]pyridazin-6-amine Chemical compound N1=CC=CC2=CC([C@H](C)C3=NN=C4C=CC(=NN43)NC(C)C)=CC=C21 LLYNUJHWODYAPQ-ZDUSSCGKSA-N 0.000 claims description 2
- WDDSVRBHOISTHU-UHFFFAOYSA-N n-(oxolan-3-yl)-3-(1-quinolin-6-ylethyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-amine Chemical compound C=1C=C2N=CC=CC2=CC=1C(C)C(N1N=2)=NN=C1C=CC=2NC1CCOC1 WDDSVRBHOISTHU-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 67
- 230000003463 hyperproliferative effect Effects 0.000 abstract description 4
- 239000000203 mixture Substances 0.000 description 75
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 58
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 57
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 50
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 49
- 239000000243 solution Substances 0.000 description 46
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 45
- 229910001868 water Inorganic materials 0.000 description 44
- 229910052757 nitrogen Inorganic materials 0.000 description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 41
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 37
- 230000000694 effects Effects 0.000 description 37
- 238000005481 NMR spectroscopy Methods 0.000 description 32
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- 210000004027 cell Anatomy 0.000 description 30
- 229910052740 iodine Inorganic materials 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
- 235000019439 ethyl acetate Nutrition 0.000 description 25
- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
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- 125000004432 carbon atom Chemical group C* 0.000 description 22
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 125000003342 alkenyl group Chemical group 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 238000003556 assay Methods 0.000 description 16
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
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- YDELTVFMAORHME-UHFFFAOYSA-N 6-[1-(6-chloro-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)ethyl]quinoline Chemical compound N1=CC=CC2=CC(C(C=3N4N=C(Cl)C=CC4=NN=3)C)=CC=C21 YDELTVFMAORHME-UHFFFAOYSA-N 0.000 description 13
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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
- 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
-
- 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
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hematology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US80346906P | 2006-05-30 | 2006-05-30 | |
| US60/803,469 | 2006-05-30 | ||
| PCT/IB2007/001446 WO2007138472A2 (fr) | 2006-05-30 | 2007-05-18 | Dérivés de la triazolopyridazine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2651979A1 true CA2651979A1 (fr) | 2007-12-06 |
Family
ID=38626862
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002651979A Abandoned CA2651979A1 (fr) | 2006-05-30 | 2007-05-18 | Derives de la triazolopyridazine |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP2032578A2 (fr) |
| JP (1) | JP2009538899A (fr) |
| CA (1) | CA2651979A1 (fr) |
| WO (1) | WO2007138472A2 (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116969955A (zh) * | 2023-09-25 | 2023-10-31 | 中国药科大学 | 一种[1,2,4]三唑[4,3-b]哒嗪类化合物及其制法与应用 |
Families Citing this family (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0620292B1 (pt) | 2005-12-21 | 2021-08-24 | Janssen Pharmaceutica N. V. | Compostos de triazolopiridazinas como moduladores da cinase, composição, uso, combinação e processo de preparo do referido composto |
| US8217177B2 (en) * | 2006-07-14 | 2012-07-10 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
| US8198448B2 (en) | 2006-07-14 | 2012-06-12 | Amgen Inc. | Fused heterocyclic derivatives and methods of use |
| PE20080403A1 (es) * | 2006-07-14 | 2008-04-25 | Amgen Inc | Derivados heterociclicos fusionados y metodos de uso |
| PL2081937T3 (pl) * | 2006-10-23 | 2013-01-31 | Sgx Pharmaceuticals Inc | Triazolopirydazynowe modulatory kinaz białkowych |
| US8188083B2 (en) | 2007-06-28 | 2012-05-29 | Abbott Laboratories | Triazolopyridazines |
| FR2919870B1 (fr) * | 2007-08-09 | 2014-05-16 | Sanofi Aventis | Nouveaux derives de 6-triazolopyridazine-sulfanyl benzothiazole et benzothiazole et benzimidazole, procede, compositions pharmaceutiques et nouvelle utilisation comme inhibiteurs de cmet |
| PA8792501A1 (es) * | 2007-08-09 | 2009-04-23 | Sanofi Aventis | Nuevos derivados de 6-triazolopiridacina-sulfanil benzotiazol y bencimidazol,su procedimiento de preparación,su aplicación como medicamentos,composiciones farmacéuticas y nueva utilización principalmente como inhibidores de met. |
| CA2717034A1 (fr) | 2008-02-28 | 2009-09-03 | Pascal Furet | Derives d'imidazo[1,2-b]pyridazine pour le traitement de maladies mediees par la tyrosine kinase c-met |
| WO2009126624A1 (fr) | 2008-04-11 | 2009-10-15 | Bristol-Myers Squibb Company | Composés triazolos utiles en tant qu'inhibiteurs de dgat1 |
| US8394823B2 (en) | 2008-04-11 | 2013-03-12 | Bristol-Myers Squibb Company | Triazolopyridine compounds useful as DGAT1 inhibitors |
| DE102008028905A1 (de) | 2008-06-18 | 2009-12-24 | Merck Patent Gmbh | 3-(3-Pyrimidin-2-yl-benzyl)-[1,2,4]triazolo[4,3-b]pyridazinderivate |
| DE102008037790A1 (de) | 2008-08-14 | 2010-02-18 | Merck Patent Gmbh | Bicyclische Triazolderivate |
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| US9284323B2 (en) | 2012-01-04 | 2016-03-15 | Gilead Sciences, Inc. | Naphthalene acetic acid derivatives against HIV infection |
| WO2013103724A1 (fr) | 2012-01-04 | 2013-07-11 | Gilead Sciences, Inc. | Dérivés d'acide 2-(tert-butoxy)-2-(7-méthylquinoléin-6-yl)acétique pour traiter le sida |
| ES2571479T3 (es) | 2012-04-20 | 2016-05-25 | Gilead Sciences Inc | Derivados del ácido benzotiazol-6-il acético y su uso para tratar una infección por VIH |
| CN104447867B (zh) * | 2013-09-17 | 2017-12-26 | 江苏天士力帝益药业有限公司 | 一种噻吩并哌啶衍生物、制备方法及其应用 |
| WO2015134854A2 (fr) * | 2014-03-06 | 2015-09-11 | Oyagen, Inc. | Antagonistes à petites molécules obtenus par dimérisation de vif à titre d'agents anti-vih et pouvant être utilisés à titre d'agents thérapeutiques |
| PL224660B1 (pl) * | 2014-07-23 | 2017-01-31 | Inst Immunologii I Terapii Doświadczalnej | Nowe analogi 1,2,4-triazoli i sposób otrzymywania analogów 1,2,4-triazoli |
| JP6864953B2 (ja) | 2014-12-09 | 2021-04-28 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | Ａｘｌに対するヒトモノクローナル抗体 |
| WO2016135041A1 (fr) | 2015-02-26 | 2016-09-01 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Protéines de fusion et anticorps les contenant pour favoriser l'apoptose |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10038019A1 (de) * | 2000-08-04 | 2002-02-14 | Bayer Ag | Substituierte Triazolopyrid(az)ine |
| KR20040087335A (ko) * | 2002-03-01 | 2004-10-13 | 야마노우치세이야쿠 가부시키가이샤 | 질소 함유 복소환 화합물 |
| JP4817661B2 (ja) * | 2002-12-18 | 2011-11-16 | バーテックス ファーマシューティカルズ インコーポレイテッド | プロテインキナーゼインヒビターとしてのトリアゾロピリダジン |
| WO2007064797A2 (fr) * | 2005-11-30 | 2007-06-07 | Vertex Pharmaceuticals Incorporated | Inhibiteurs de c-met et leurs utilisations |
| BRPI0620292B1 (pt) * | 2005-12-21 | 2021-08-24 | Janssen Pharmaceutica N. V. | Compostos de triazolopiridazinas como moduladores da cinase, composição, uso, combinação e processo de preparo do referido composto |
-
2007
- 2007-05-18 JP JP2009512702A patent/JP2009538899A/ja not_active Withdrawn
- 2007-05-18 CA CA002651979A patent/CA2651979A1/fr not_active Abandoned
- 2007-05-18 WO PCT/IB2007/001446 patent/WO2007138472A2/fr active Application Filing
- 2007-05-18 EP EP07734734A patent/EP2032578A2/fr not_active Withdrawn
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116969955A (zh) * | 2023-09-25 | 2023-10-31 | 中国药科大学 | 一种[1,2,4]三唑[4,3-b]哒嗪类化合物及其制法与应用 |
| CN116969955B (zh) * | 2023-09-25 | 2023-12-19 | 中国药科大学 | 一种[1,2,4]三唑[4,3-b]哒嗪类化合物及其制法与应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007138472A3 (fr) | 2008-02-07 |
| WO2007138472A2 (fr) | 2007-12-06 |
| EP2032578A2 (fr) | 2009-03-11 |
| JP2009538899A (ja) | 2009-11-12 |
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